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A large number of structural determinations of compounds containing 2-hy­droxy-3,5-di­nitro­benzoic acid and its various deprotonated forms, 2-hy­droxy-3,5-di­nitro­benzoate or 2-carb­oxy-4,6-di­nitro­phenolate, are biased. The reason for the bias follows from incorrectly applied constraints or restraints on the bridging hydrogen, which is involved in the intra­molecular hydrogen bond between the neighbouring carb­oxy­lic/carboxyl­ate and oxo/hy­droxy groups. The present article examines the problem of the location and refinement of such a bridging hydrogen in a number of reported compounds. The analysis of the intra­molecular hydrogen bonding is also discussed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989018011544/su5452sup1.cif
Contains datablocks global, DUJZAK, JEVNAA, NUQVEB, QIQJAD, SEDKET, VABZIJ, WADXOR, YAXPOE, LUDFUL, SAFGUD, TIYZIM, TUJPEV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018011544/su5452DUJZAKsup2.hkl
Contains datablock DUJZAK

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018011544/su5452JEVNAAsup3.hkl
Contains datablock JEVNAA

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018011544/su5452LUDFULsup4.hkl
Contains datablock LUDFUL

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018011544/su5452NUQVEBsup5.hkl
Contains datablock NUQVEB

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018011544/su5452QIQJADsup6.hkl
Contains datablock QIQJAD

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018011544/su5452SAFGUDsup7.hkl
Contains datablock SAFGUD

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018011544/su5452TIYZIMsup8.hkl
Contains datablock TIYZIM

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018011544/su5452TUJPEVsup9.hkl
Contains datablock TUJPEV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018011544/su5452VABZIJsup10.hkl
Contains datablock VABZIJ

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018011544/su5452WADXORsup11.hkl
Contains datablock WADXOR

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018011544/su5452YAXPOEsup12.hkl
Contains datablock YAXPOE

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018011544/su5452SEDKETsup13.hkl
Contains datablock SEDKET

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018011544/su5452NUQVEBsup14.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018011544/su5452QIQJADsup15.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018011544/su5452SEDKETsup16.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018011544/su5452TIYZIMsup17.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018011544/su5452TUJPEVsup18.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018011544/su5452VABZIJsup19.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018011544/su5452WADXORsup20.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018011544/su5452YAXPOEsup21.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2056989018011544/su5452sup21.pdf
Supplementary material

CCDC references: 1862187; 1862188; 1862189; 1862190; 1862191; 1862192; 1862193; 1862194; 1862195; 1862196; 1862197; 1862198

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • Mean [sigma](C-C) = 0.003 Å
  • Mean [sigma](C-C) = 0.003 Å
  • Mean [sigma](C-C) = 0.002 Å
  • Mean [sigma](C-C) = 0.003 Å
  • Mean [sigma](C-C) = 0.009 Å
  • Mean [sigma](C-C) = 0.005 Å
  • Mean [sigma](C-C) = 0.002 Å
  • Mean [sigma](C-C) = 0.002 Å
  • Mean [sigma](C-C) = 0.002 Å
  • Mean [sigma](C-C) = 0.003 Å
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in main residue
  • R factor = 0.023
  • wR factor = 0.053
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Datablock: DUJZAK


Alert level B PLAT772_ALERT_2_B Suspect O-H Bond in CIF: O9 --H3B .. 1.50 Ang.
Alert level C PLAT090_ALERT_3_C Poor Data / Parameter Ratio (Zmax > 18) ........ 7.96 Note PLAT223_ALERT_4_C Solv./Anion Resd 2 H Ueq(max)/Ueq(min) Range 10.0 Ratio PLAT355_ALERT_3_C Long O-H (X0.82,N0.98A) O3 - H3B . 1.04 Ang. PLAT751_ALERT_4_C Bond Calc 0.76000, Rep 0.7585(19) ...... Senseless s.u. O1 -H1AA 1.555 1.555 ........ # 2 Check PLAT751_ALERT_4_C Bond Calc 0.92000, Rep 0.922(2) ...... Senseless s.u. O2 -H2AA 1.555 1.555 ........ # 4 Check PLAT751_ALERT_4_C Bond Calc 1.04000, Rep 1.040(2) ...... Senseless s.u. O3 -H3B 1.555 1.555 ........ # 40 Check PLAT751_ALERT_4_C Bond Calc 1.50000, Rep 1.4952(19) ...... Senseless s.u. O9 -H3B 1.555 1.555 ........ # 47 Check PLAT752_ALERT_4_C Angle Calc 118.00, Rep 118.2(2) ...... Senseless s.u. C8 -O1 -H1AA 1.555 1.555 1.555 # 1 Check PLAT752_ALERT_4_C Angle Calc 112.00, Rep 111.60(19) ...... Senseless s.u. C17 -O2 -H2AA 1.555 1.555 1.555 # 2 Check PLAT752_ALERT_4_C Angle Calc 103.00, Rep 102.89(19) ...... Senseless s.u. C22 -O3 -H3B 1.555 1.555 1.555 # 59 Check PLAT752_ALERT_4_C Angle Calc 103.00, Rep 102.84(17) ...... Senseless s.u. C25 -O9 -H3B 1.555 1.555 1.555 # 60 Check PLAT752_ALERT_4_C Angle Calc 156.00, Rep 155.88(12) ...... Senseless s.u. O3 -H3B -O9 1.555 1.555 1.555 # 88 Check PLAT755_ALERT_4_C D-H Calc 0.76000, Rep 0.7585(19) ...... Senseless s.u. O1 -H1AA 1.555 1.555 ........ # 58 Check PLAT755_ALERT_4_C D-H Calc 0.92000, Rep 0.922(2) ...... Senseless s.u. O2 -H2AA 1.555 1.555 ........ # 58 Check PLAT755_ALERT_4_C D-H Calc 1.04000, Rep 1.040(2) ...... Senseless s.u. O3 -H3B 1.555 1.555 ........ # 58 Check PLAT756_ALERT_4_C H...A Calc 1.86000, Rep 1.859(2) ...... Senseless s.u. H1AA -O8 1.555 1.555 ........ # 58 Check PLAT756_ALERT_4_C H...A Calc 1.73000, Rep 1.727(2) ...... Senseless s.u. H2AA -O9 1.555 1.555 ........ # 58 Check PLAT756_ALERT_4_C H...A Calc 1.50000, Rep 1.4952(19) ...... Senseless s.u. H3B -O9 1.555 1.555 ........ # 58 Check PLAT758_ALERT_4_C D-H..A Calc 168.00, Rep 167.96(14) ...... Senseless s.u. O1 -H1AA -O8 1.555 1.555 1.555 # 88 Check PLAT758_ALERT_4_C D-H..A Calc 166.00, Rep 166.48(15) ...... Senseless s.u. O2 -H2AA -O9 1.555 1.555 1.555 # 88 Check PLAT758_ALERT_4_C D-H..A Calc 156.00, Rep 155.88(12) ...... Senseless s.u. O3 -H3B -O9 1.555 1.555 1.555 # 88 Check
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 3 Report PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as mixed Check PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 2 Note PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note C7 H3 N2 O7 PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2018 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 21 ALERT level C = Check. Ensure it is not caused by an omission or oversight 8 ALERT level G = General information/check it is not something unexpected 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 22 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Datablock: JEVNAA

Alert level B PLAT772_ALERT_2_B Suspect O-H Bond in CIF: O1 --H1A .. 1.50 Ang.
Alert level C PLAT355_ALERT_3_C Long O-H (X0.82,N0.98A) O2 - H1A . 1.04 Ang. PLAT751_ALERT_4_C Bond Calc 0.94000, Rep 0.9427(18) ...... Senseless s.u. N4 -H4A 1.555 1.555 ........ # 13 Check PLAT751_ALERT_4_C Bond Calc 0.97000, Rep 0.967(2) ...... Senseless s.u. N2 -H2A 1.555 1.555 ........ # 31 Check PLAT751_ALERT_4_C Bond Calc 1.50000, Rep 1.4955(15) ...... Senseless s.u. O1 -H1A 1.555 1.555 ........ # 37 Check PLAT751_ALERT_4_C Bond Calc 1.04000, Rep 1.0386(15) ...... Senseless s.u. O2 -H1A 1.555 1.555 ........ # 38 Check PLAT752_ALERT_4_C Angle Calc 134.00, Rep 133.8(2) ...... Senseless s.u. C4 -N4 -H4A 1.555 1.555 1.555 # 14 Check PLAT752_ALERT_4_C Angle Calc 118.00, Rep 118.5(2) ...... Senseless s.u. C5 -N4 -H4A 1.555 1.555 1.555 # 15 Check PLAT752_ALERT_4_C Angle Calc 121.00, Rep 121.3(2) ...... Senseless s.u. C2 -N2 -H2A 1.555 1.555 1.555 # 42 Check PLAT752_ALERT_4_C Angle Calc 131.00, Rep 131.3(2) ...... Senseless s.u. C3 -N2 -H2A 1.555 1.555 1.555 # 43 Check PLAT752_ALERT_4_C Angle Calc 99.00, Rep 98.67(13) ...... Senseless s.u. C10 -O1 -H1A 1.555 1.555 1.555 # 54 Check PLAT752_ALERT_4_C Angle Calc 103.00, Rep 102.66(16) ...... Senseless s.u. C13 -O2 -H1A 1.555 1.555 1.555 # 55 Check PLAT752_ALERT_4_C Angle Calc 160.00, Rep 160.37(10) ...... Senseless s.u. O1 -H1A -O2 1.555 1.555 1.555 # 56 Check PLAT755_ALERT_4_C D-H Calc 1.04000, Rep 1.0386(15) ...... Senseless s.u. O2 -H1A 1.555 1.555 ........ # 38 Check PLAT755_ALERT_4_C D-H Calc 1.04000, Rep 1.0386(15) ...... Senseless s.u. O2 -H1A 1.555 1.555 ........ # 38 Check PLAT755_ALERT_4_C D-H Calc 0.97000, Rep 0.967(2) ...... Senseless s.u. N2 -H2A 1.555 1.555 ........ # 38 Check PLAT755_ALERT_4_C D-H Calc 0.94000, Rep 0.9427(18) ...... Senseless s.u. N4 -H4A 1.555 1.555 ........ # 38 Check PLAT755_ALERT_4_C D-H Calc 0.94000, Rep 0.9427(18) ...... Senseless s.u. N4 -H4A 1.555 1.555 ........ # 38 Check PLAT756_ALERT_4_C H...A Calc 2.11000, Rep 2.110(2) ...... Senseless s.u. H1A -C10 1.555 1.555 ........ # 38 Check PLAT756_ALERT_4_C H...A Calc 1.50000, Rep 1.4955(15) ...... Senseless s.u. H1A -O1 1.555 1.555 ........ # 38 Check PLAT756_ALERT_4_C H...A Calc 1.89000, Rep 1.8902(16) ...... Senseless s.u. H2A -O3 1.555 1.555 ........ # 38 Check PLAT756_ALERT_4_C H...A Calc 1.92000, Rep 1.9236(14) ...... Senseless s.u. H4A -O1 1.555 6.656 ........ # 38 Check PLAT756_ALERT_4_C H...A Calc 2.43000, Rep 2.4336(18) ...... Senseless s.u. H4A -O7 1.555 6.656 ........ # 38 Check PLAT758_ALERT_4_C D-H..A Calc 124.00, Rep 123.50(10) ...... Senseless s.u. O2 -H1A -C10 1.555 1.555 1.555 # 56 Check PLAT758_ALERT_4_C D-H..A Calc 160.00, Rep 160.40(10) ...... Senseless s.u. O2 -H1A -O1 1.555 1.555 1.555 # 56 Check PLAT758_ALERT_4_C D-H..A Calc 166.00, Rep 165.87(12) ...... Senseless s.u. N2 -H2A -O3 1.555 1.555 1.555 # 56 Check
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 3 Report PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as mixed Check PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT432_ALERT_2_G Short Inter X...Y Contact O7 ..C13 3.01 Ang. 3/2-x,3/2-y,1-z = 7_666 Check PLAT794_ALERT_5_G Tentative Bond Valency for Zn1 (II) . 1.94 Info PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2018 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 25 ALERT level C = Check. Ensure it is not caused by an omission or oversight 9 ALERT level G = General information/check it is not something unexpected 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 25 ALERT type 4 Improvement, methodology, query or suggestion 3 ALERT type 5 Informative message, check
Datablock: LUDFUL

Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections (too) Low .. 38% Check
Alert level C PLAT125_ALERT_4_C No '_symmetry_space_group_name_Hall' Given ..... Please Do ! PLAT230_ALERT_2_C Hirshfeld Test Diff for O7 --N2 . 5.4 s.u. PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 --C7 . 5.3 s.u. PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of N1 Check PLAT303_ALERT_2_C Full Occupancy Atom H1A with # Connections 2.00 Check PLAT355_ALERT_3_C Long O-H (X0.82,N0.98A) O3 - H3A . 1.06 Ang. PLAT751_ALERT_4_C Bond Calc 1.06000, Rep 1.0592(14) ...... Senseless s.u. O3 -H3A 1.555 1.555 ........ # 2 Check PLAT751_ALERT_4_C Bond Calc 1.16000, Rep 1.1628(13) ...... Senseless s.u. O1 -H1A 1.555 1.555 ........ # 4 Check PLAT752_ALERT_4_C Angle Calc 106.00, Rep 105.60(13) ...... Senseless s.u. C2 -O3 -H3A 1.555 1.555 1.555 # 1 Check PLAT752_ALERT_4_C Angle Calc 114.00, Rep 113.94(15) ...... Senseless s.u. C7 -O1 -H1A 1.555 1.555 1.555 # 2 Check PLAT752_ALERT_4_C Angle Calc 102.00, Rep 102.24(13) ...... Senseless s.u. C7 -O2 -H3A 1.555 1.555 1.555 # 12 Check PLAT752_ALERT_4_C Angle Calc 119.00, Rep 119.38(14) ...... Senseless s.u. C19 -N3 -H1A 1.555 1.555 1.555 # 32 Check PLAT752_ALERT_4_C Angle Calc 121.00, Rep 120.79(14) ...... Senseless s.u. C16 -N3 -H1A 1.555 1.555 1.555 # 33 Check PLAT752_ALERT_4_C Angle Calc 152.00, Rep 151.72(10) ...... Senseless s.u. O3 -H3A -O2 1.555 1.555 1.555 # 71 Check PLAT752_ALERT_4_C Angle Calc 163.00, Rep 163.24(10) ...... Senseless s.u. O1 -H1A -N3 1.555 1.555 1.555 # 72 Check PLAT755_ALERT_4_C D-H Calc 1.06000, Rep 1.0592(14) ...... Senseless s.u. O3 -H3A 1.555 1.555 ........ # 44 Check PLAT755_ALERT_4_C D-H Calc 1.16000, Rep 1.1628(13) ...... Senseless s.u. O1 -H1A 1.555 1.555 ........ # 44 Check PLAT756_ALERT_4_C H...A Calc 1.53000, Rep 1.5297(14) ...... Senseless s.u. H3A -O2 1.555 1.555 ........ # 44 Check PLAT756_ALERT_4_C H...A Calc 1.42000, Rep 1.4160(14) ...... Senseless s.u. H1A -N3 1.555 1.555 ........ # 44 Check PLAT758_ALERT_4_C D-H..A Calc 152.00, Rep 151.72(10) ...... Senseless s.u. O3 -H3A -O2 1.555 1.555 1.555 # 72 Check PLAT758_ALERT_4_C D-H..A Calc 163.00, Rep 163.24(10) ...... Senseless s.u. O1 -H1A -N3 1.555 1.555 1.555 # 72 Check
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as mixed Check PLAT128_ALERT_4_G Alternate Setting for Input Space Group P21/a P21/c Note PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 21 ALERT level C = Check. Ensure it is not caused by an omission or oversight 7 ALERT level G = General information/check it is not something unexpected 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 17 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Datablock: NUQVEB

Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 2.060 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low . 0.962 Why? PLAT751_ALERT_4_C Bond Calc 0.90000, Rep 0.8977(9) ...... Senseless s.u. N1 -H1 1.555 1.555 ........ # 3 Check PLAT751_ALERT_4_C Bond Calc 0.89000, Rep 0.8921(9) ...... Senseless s.u. N2 -H2A 1.555 1.555 ........ # 5 Check PLAT751_ALERT_4_C Bond Calc 0.85000, Rep 0.8456(10) ...... Senseless s.u. N2 -H2B 1.555 1.555 ........ # 6 Check PLAT751_ALERT_4_C Bond Calc 1.50000, Rep 1.49896(19) ...... Senseless s.u. H2A -H2B 1.555 1.555 ........ # 41 Check PLAT752_ALERT_4_C Angle Calc 120.00, Rep 120.41(9) ...... Senseless s.u. C1 -N1 -H1 1.555 1.555 1.555 # 2 Check PLAT752_ALERT_4_C Angle Calc 116.00, Rep 116.29(10) ...... Senseless s.u. C2 -N1 -H1 1.555 1.555 1.555 # 3 Check PLAT752_ALERT_4_C Angle Calc 121.00, Rep 120.74(11) ...... Senseless s.u. C1 -N2 -H2A 1.555 1.555 1.555 # 4 Check PLAT752_ALERT_4_C Angle Calc 120.00, Rep 120.05(10) ...... Senseless s.u. C1 -N2 -H2B 1.555 1.555 1.555 # 5 Check PLAT752_ALERT_4_C Angle Calc 119.00, Rep 119.20(10) ...... Senseless s.u. H2A -N2 -H2B 1.555 1.555 1.555 # 6 Check PLAT755_ALERT_4_C D-H Calc 0.89000, Rep 0.8921(9) ...... Senseless s.u. N2 -H2A 1.555 1.555 ........ # 41 Check PLAT755_ALERT_4_C D-H Calc 0.85000, Rep 0.8456(10) ...... Senseless s.u. N2 -H2B 1.555 1.555 ........ # 41 Check PLAT755_ALERT_4_C D-H Calc 0.85000, Rep 0.8456(10) ...... Senseless s.u. N2 -H2B 1.555 1.555 ........ # 41 Check PLAT755_ALERT_4_C D-H Calc 0.90000, Rep 0.8977(9) ...... Senseless s.u. N1 -H1 1.555 1.555 ........ # 41 Check PLAT756_ALERT_4_C H...A Calc 2.08000, Rep 2.0783(9) ...... Senseless s.u. H2A -O7 1.555 2.665 ........ # 41 Check PLAT756_ALERT_4_C H...A Calc 2.16000, Rep 2.1644(9) ...... Senseless s.u. H2B -O1 1.555 1.655 ........ # 41 Check PLAT756_ALERT_4_C H...A Calc 2.41000, Rep 2.4133(10) ...... Senseless s.u. H2B -O2 1.555 1.655 ........ # 41 Check PLAT756_ALERT_4_C H...A Calc 1.78000, Rep 1.7828(9) ...... Senseless s.u. H1 -O6 1.555 2.665 ........ # 41 Check
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 5 Report PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as mixed Check PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.003 Degree PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 2 Note PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2018 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 19 ALERT level C = Check. Ensure it is not caused by an omission or oversight 8 ALERT level G = General information/check it is not something unexpected 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 19 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Datablock: QIQJAD

Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C3 --C4 . 8.3 s.u. PLAT230_ALERT_2_B Hirshfeld Test Diff for C5 --C6 . 9.7 s.u.
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 3.410 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.22 Report PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of N6 Check PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of N8 Check PLAT751_ALERT_4_C Bond Calc 0.90000, Rep 0.8973(16) ...... Senseless s.u. N2 -H2N 1.555 1.555 ........ # 19 Check PLAT751_ALERT_4_C Bond Calc 0.86000, Rep 0.8624(18) ...... Senseless s.u. N3 -H3N 1.555 1.555 ........ # 20 Check PLAT751_ALERT_4_C Bond Calc 0.86000, Rep 0.8630(15) ...... Senseless s.u. N3 -H4N 1.555 1.555 ........ # 21 Check PLAT751_ALERT_4_C Bond Calc 0.87000, Rep 0.8658(14) ...... Senseless s.u. N5 -H5N 1.555 1.555 ........ # 22 Check PLAT751_ALERT_4_C Bond Calc 0.86000, Rep 0.8630(16) ...... Senseless s.u. N5 -H6N 1.555 1.555 ........ # 23 Check PLAT751_ALERT_4_C Bond Calc 0.93000, Rep 0.9258(14) ...... Senseless s.u. O3 -H3O 1.555 1.555 ........ # 42 Check PLAT752_ALERT_4_C Angle Calc 122.00, Rep 122.42(17) ...... Senseless s.u. C8 -N2 -H2N 1.555 1.555 1.555 # 26 Check PLAT752_ALERT_4_C Angle Calc 114.00, Rep 113.82(14) ...... Senseless s.u. N1 -N2 -H2N 1.555 1.555 1.555 # 27 Check PLAT752_ALERT_4_C Angle Calc 122.00, Rep 122.28(17) ...... Senseless s.u. C8 -N3 -H3N 1.555 1.555 1.555 # 28 Check PLAT752_ALERT_4_C Angle Calc 121.00, Rep 121.07(18) ...... Senseless s.u. C8 -N3 -H4N 1.555 1.555 1.555 # 29 Check PLAT752_ALERT_4_C Angle Calc 116.00, Rep 116.2(2) ...... Senseless s.u. H3N -N3 -H4N 1.555 1.555 1.555 # 30 Check PLAT752_ALERT_4_C Angle Calc 120.00, Rep 119.55(17) ...... Senseless s.u. C9 -N5 -H5N 1.555 1.555 1.555 # 32 Check PLAT752_ALERT_4_C Angle Calc 125.00, Rep 124.81(16) ...... Senseless s.u. C9 -N5 -H6N 1.555 1.555 1.555 # 33 Check PLAT752_ALERT_4_C Angle Calc 116.00, Rep 115.64(18) ...... Senseless s.u. H5N -N5 -H6N 1.555 1.555 1.555 # 34 Check PLAT752_ALERT_4_C Angle Calc 101.00, Rep 101.27(12) ...... Senseless s.u. C10 -O1 -H3O 1.555 1.555 1.555 # 62 Check PLAT752_ALERT_4_C Angle Calc 99.00, Rep 99.28(14) ...... Senseless s.u. C12 -O3 -H3O 1.555 1.555 1.555 # 63 Check PLAT752_ALERT_4_C Angle Calc 161.00, Rep 161.33(12) ...... Senseless s.u. O1 -H3O -O3 1.555 1.555 1.555 # 82 Check PLAT755_ALERT_4_C D-H Calc 0.86000, Rep 0.8624(18) ...... Senseless s.u. N3 -H3N 1.555 1.555 ........ # 59 Check PLAT755_ALERT_4_C D-H Calc 0.86000, Rep 0.8630(15) ...... Senseless s.u. N3 -H4N 1.555 1.555 ........ # 59 Check PLAT755_ALERT_4_C D-H Calc 0.90000, Rep 0.8973(16) ...... Senseless s.u. N2 -H2N 1.555 1.555 ........ # 59 Check PLAT755_ALERT_4_C D-H Calc 0.87000, Rep 0.8658(14) ...... Senseless s.u. N5 -H5N 1.555 1.555 ........ # 59 Check PLAT755_ALERT_4_C D-H Calc 0.86000, Rep 0.8630(16) ...... Senseless s.u. N5 -H6N 1.555 1.555 ........ # 59 Check PLAT755_ALERT_4_C D-H Calc 0.93000, Rep 0.9258(14) ...... Senseless s.u. O3 -H3O 1.555 1.555 ........ # 59 Check PLAT756_ALERT_4_C H...A Calc 1.99000, Rep 1.9939(16) ...... Senseless s.u. H3N -O2 1.555 1.555 ........ # 59 Check PLAT756_ALERT_4_C H...A Calc 2.06000, Rep 2.0586(14) ...... Senseless s.u. H4N -O8 1.555 2.666 ........ # 59 Check PLAT756_ALERT_4_C H...A Calc 1.83000, Rep 1.8310(15) ...... Senseless s.u. H2N -O1 1.555 1.555 ........ # 59 Check PLAT756_ALERT_4_C H...A Calc 2.14000, Rep 2.1409(13) ...... Senseless s.u. H5N -N4 1.555 2.576 ........ # 59 Check PLAT756_ALERT_4_C H...A Calc 2.04000, Rep 2.0412(16) ...... Senseless s.u. H6N -O8 1.555 1.465 ........ # 59 Check PLAT756_ALERT_4_C H...A Calc 1.56000, Rep 1.5621(12) ...... Senseless s.u. H3O -O1 1.555 1.555 ........ # 59 Check PLAT758_ALERT_4_C D-H..A Calc 175.00, Rep 174.78(11) ...... Senseless s.u. N3 -H3N -O2 1.555 1.555 1.555 # 82 Check PLAT758_ALERT_4_C D-H..A Calc 177.00, Rep 177.45(12) ...... Senseless s.u. N2 -H2N -O1 1.555 1.555 1.555 # 82 Check PLAT758_ALERT_4_C D-H..A Calc 161.00, Rep 161.33(12) ...... Senseless s.u. O3 -H3O -O1 1.555 1.555 1.555 # 82 Check
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 6 Report PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as mixed Check PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.001 Degree PLAT432_ALERT_2_G Short Inter X...Y Contact O7 ..C17 2.96 Ang. 2-x,1-y,1-z = 2_766 Check PLAT432_ALERT_2_G Short Inter X...Y Contact O7 ..C19 2.96 Ang. x,y,1+z = 1_556 Check
0 ALERT level A = Most likely a serious problem - resolve or explain 2 ALERT level B = A potentially serious problem, consider carefully 36 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 33 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Datablock: SAFGUD

Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C6 --C7 . 21.7 s.u.
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 --C5 . 6.4 s.u. PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of C6 Check PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C7 Check PLAT245_ALERT_2_C U(iso) H7 Smaller than U(eq) O8 by 0.047 Ang   2 PLAT303_ALERT_2_C Full Occupancy Atom H7 with # Connections 2.00 Check PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.0089 Ang. PLAT751_ALERT_4_C Bond Calc 1.35000, Rep 1.346(4) ...... Senseless s.u. O7 -H7 1.555 1.555 ........ # 71 Check PLAT751_ALERT_4_C Bond Calc 1.16000, Rep 1.155(4) ...... Senseless s.u. O8 -H7 1.555 1.555 ........ # 72 Check PLAT752_ALERT_4_C Angle Calc 99.00, Rep 99.4(4) ...... Senseless s.u. C26 -O7 -H7 1.555 1.555 1.555 # 104 Check PLAT752_ALERT_4_C Angle Calc 104.00, Rep 103.7(4) ...... Senseless s.u. C31 -O8 -H7 1.555 1.555 1.555 # 105 Check PLAT752_ALERT_4_C Angle Calc 160.00, Rep 159.6(3) ...... Senseless s.u. O7 -H7 -O8 1.555 1.555 1.555 # 106 Check PLAT755_ALERT_4_C D-H Calc 1.35000, Rep 1.346(4) ...... Senseless s.u. O7 -H7 1.555 1.555 ........ # 72 Check PLAT755_ALERT_4_C D-H Calc 1.35000, Rep 1.346(4) ...... Senseless s.u. O7 -H7 1.555 1.555 ........ # 72 Check PLAT755_ALERT_4_C D-H Calc 1.16000, Rep 1.155(4) ...... Senseless s.u. O8 -H7 1.555 1.555 ........ # 72 Check PLAT755_ALERT_4_C D-H Calc 1.16000, Rep 1.155(4) ...... Senseless s.u. O8 -H7 1.555 1.555 ........ # 72 Check PLAT756_ALERT_4_C H...A Calc 1.92000, Rep 1.922(7) ...... Senseless s.u. H7 -C31 1.555 1.555 ........ # 72 Check PLAT756_ALERT_4_C H...A Calc 1.16000, Rep 1.155(4) ...... Senseless s.u. H7 -O8 1.555 1.555 ........ # 72 Check PLAT756_ALERT_4_C H...A Calc 2.01000, Rep 2.013(6) ...... Senseless s.u. H7 -C26 1.555 1.555 ........ # 72 Check PLAT756_ALERT_4_C H...A Calc 1.35000, Rep 1.346(4) ...... Senseless s.u. H7 -O7 1.555 1.555 ........ # 72 Check PLAT758_ALERT_4_C D-H..A Calc 119.00, Rep 119.1(3) ...... Senseless s.u. O7 -H7 -C31 1.555 1.555 1.555 # 106 Check PLAT758_ALERT_4_C D-H..A Calc 160.00, Rep 159.6(3) ...... Senseless s.u. O7 -H7 -O8 1.555 1.555 1.555 # 106 Check PLAT758_ALERT_4_C D-H..A Calc 120.00, Rep 120.3(3) ...... Senseless s.u. O8 -H7 -C26 1.555 1.555 1.555 # 106 Check PLAT758_ALERT_4_C D-H..A Calc 160.00, Rep 159.6(3) ...... Senseless s.u. O8 -H7 -O7 1.555 1.555 1.555 # 106 Check PLAT772_ALERT_2_C Suspect O-H Bond in CIF: O7 --H7 .. 1.35 Ang. PLAT776_ALERT_1_C Suspect D-H Dist in CIF: O7 --H7 .. 1.35 Ang. PLAT776_ALERT_1_C Suspect D-H Dist in CIF: O7 --H7 .. 1.35 Ang.
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT333_ALERT_2_G Large Aver C6-Ring C-C Dist. C4 -C12 1.43 Ang. PLAT333_ALERT_2_G Large Aver C6-Ring C-C Dist. C16 -C24 1.45 Ang. PLAT432_ALERT_2_G Short Inter X...Y Contact O1 ..C18 2.96 Ang. 1-x,1-y,1-z = 3_666 Check PLAT432_ALERT_2_G Short Inter X...Y Contact O9 ..C17 2.74 Ang. -x,1-y,1-z = 3_566 Check PLAT432_ALERT_2_G Short Inter X...Y Contact O9 ..C18 2.90 Ang. -x,1-y,1-z = 3_566 Check PLAT432_ALERT_2_G Short Inter X...Y Contact O9 ..C16 2.93 Ang. -x,1-y,1-z = 3_566 Check
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 26 ALERT level C = Check. Ensure it is not caused by an omission or oversight 9 ALERT level G = General information/check it is not something unexpected 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 13 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 17 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Datablock: SEDKET

Alert level B PLAT353_ALERT_3_B Long N-H (N0.87,N1.01A) N1 - H1 . 1.11 Ang.
Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.500 From the CIF: _refine_ls_abs_structure_Flack_su 0.000 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........ 6.38 Note PLAT125_ALERT_4_C No '_symmetry_space_group_name_Hall' Given ..... Please Do ! PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 --C12 . 5.5 s.u. PLAT303_ALERT_2_C Full Occupancy Atom H2A with # Connections 2.00 Check PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00445 Ang. PLAT430_ALERT_2_C Short Inter D...A Contact O2 ..O3 2.89 Ang. 1-x,-1/2+y,1-z = 2_646 Check PLAT772_ALERT_2_C Suspect O-H Bond in CIF: O2 --H2A .. 1.34 Ang. PLAT776_ALERT_1_C Suspect D-H Dist in CIF: O2 --H2A .. 1.34 Ang.
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT033_ALERT_4_G Flack x Value Deviates > 3.0 * sigma from Zero . 0.500 Note PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT432_ALERT_2_G Short Inter X...Y Contact O2 ..C6 2.94 Ang. 1-x,-1/2+y,1-z = 2_646 Check PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2018 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 9 ALERT level C = Check. Ensure it is not caused by an omission or oversight 8 ALERT level G = General information/check it is not something unexpected 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Datablock: TIYZIM

Alert level C PLAT751_ALERT_4_C Bond Calc 0.98000, Rep 0.9820(12) ...... Senseless s.u. O2B -H2B 1.555 1.555 ........ # 3 Check PLAT751_ALERT_4_C Bond Calc 0.90000, Rep 0.9042(14) ...... Senseless s.u. N3A -H3AA 1.555 1.555 ........ # 26 Check PLAT751_ALERT_4_C Bond Calc 0.90000, Rep 0.9009(13) ...... Senseless s.u. N3A -H3AB 1.555 1.555 ........ # 27 Check PLAT751_ALERT_4_C Bond Calc 0.89000, Rep 0.8932(14) ...... Senseless s.u. N3A -H3AC 1.555 1.555 ........ # 28 Check PLAT752_ALERT_4_C Angle Calc 100.00, Rep 99.82(10) ...... Senseless s.u. C1B -O1B -H2B 1.555 1.555 1.555 # 1 Check PLAT752_ALERT_4_C Angle Calc 107.00, Rep 106.90(11) ...... Senseless s.u. C7B -O2B -H2B 1.555 1.555 1.555 # 2 Check PLAT752_ALERT_4_C Angle Calc 111.00, Rep 111.33(12) ...... Senseless s.u. C6A -N3A -H3AA 1.555 1.555 1.555 # 34 Check PLAT752_ALERT_4_C Angle Calc 109.00, Rep 109.46(13) ...... Senseless s.u. C6A -N3A -H3AB 1.555 1.555 1.555 # 35 Check PLAT752_ALERT_4_C Angle Calc 112.00, Rep 111.76(15) ...... Senseless s.u. C6A -N3A -H3AC 1.555 1.555 1.555 # 36 Check PLAT752_ALERT_4_C Angle Calc 110.00, Rep 110.21(16) ...... Senseless s.u. H3AA -N3A -H3AB 1.555 1.555 1.555 # 37 Check PLAT752_ALERT_4_C Angle Calc 107.00, Rep 106.71(14) ...... Senseless s.u. H3AA -N3A -H3AC 1.555 1.555 1.555 # 38 Check PLAT752_ALERT_4_C Angle Calc 107.00, Rep 107.27(13) ...... Senseless s.u. H3AB -N3A -H3AC 1.555 1.555 1.555 # 39 Check PLAT752_ALERT_4_C Angle Calc 156.00, Rep 156.29(9) ...... Senseless s.u. O1B -H2B -O2B 1.555 1.555 1.555 # 67 Check PLAT755_ALERT_4_C D-H Calc 0.98000, Rep 0.9820(12) ...... Senseless s.u. O2B -H2B 1.555 1.555 ........ # 40 Check PLAT755_ALERT_4_C D-H Calc 0.98000, Rep 0.9820(12) ...... Senseless s.u. O2B -H2B 1.555 1.555 ........ # 40 Check PLAT755_ALERT_4_C D-H Calc 0.90000, Rep 0.9042(14) ...... Senseless s.u. N3A -H3AA 1.555 1.555 ........ # 40 Check PLAT755_ALERT_4_C D-H Calc 0.90000, Rep 0.9009(13) ...... Senseless s.u. N3A -H3AB 1.555 1.555 ........ # 40 Check PLAT755_ALERT_4_C D-H Calc 0.90000, Rep 0.9009(13) ...... Senseless s.u. N3A -H3AB 1.555 1.555 ........ # 40 Check PLAT755_ALERT_4_C D-H Calc 0.89000, Rep 0.8932(14) ...... Senseless s.u. N3A -H3AC 1.555 1.555 ........ # 40 Check PLAT755_ALERT_4_C D-H Calc 0.89000, Rep 0.8932(14) ...... Senseless s.u. N3A -H3AC 1.555 1.555 ........ # 40 Check PLAT756_ALERT_4_C H...A Calc 1.52000, Rep 1.5161(11) ...... Senseless s.u. H2B -O1B 1.555 1.555 ........ # 40 Check PLAT756_ALERT_4_C H...A Calc 2.15000, Rep 2.1471(15) ...... Senseless s.u. H2B -C1B 1.555 1.555 ........ # 40 Check PLAT756_ALERT_4_C H...A Calc 1.93000, Rep 1.9318(14) ...... Senseless s.u. H3AA -N1A 1.555 2.555 ........ # 40 Check PLAT756_ALERT_4_C H...A Calc 2.56000, Rep 2.5650(12) ...... Senseless s.u. H3AB -O2B 1.555 1.655 ........ # 40 Check PLAT756_ALERT_4_C H...A Calc 2.07000, Rep 2.0721(11) ...... Senseless s.u. H3AB -O3B 1.555 1.655 ........ # 40 Check PLAT756_ALERT_4_C H...A Calc 2.06000, Rep 2.0610(13) ...... Senseless s.u. H3AC -O1B 1.555 2.566 ........ # 40 Check PLAT756_ALERT_4_C H...A Calc 2.48000, Rep 2.4844(13) ...... Senseless s.u. H3AC -O7B 1.555 2.566 ........ # 40 Check PLAT758_ALERT_4_C D-H..A Calc 156.00, Rep 156.29(9) ...... Senseless s.u. O2B -H2B -O1B 1.555 1.555 1.555 # 67 Check PLAT758_ALERT_4_C D-H..A Calc 121.00, Rep 121.00(8) ...... Senseless s.u. O2B -H2B -C1B 1.555 1.555 1.555 # 67 Check
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 4 Report PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as mixed Check PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 9 Note PLAT882_ALERT_1_G No Datum for _diffrn_reflns_av_unetI/netI ...... Please Do !
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 29 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 30 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Datablock: TUJPEV

Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O9 --N5 . 8.4 s.u.
Alert level C PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of N4 Check PLAT303_ALERT_2_C Full Occupancy Atom H6A with # Connections 2.00 Check PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C1 -C6 1.37 Ang. PLAT430_ALERT_2_C Short Inter D...A Contact O4 ..O7 2.88 Ang. 1+x,y,z = 1_655 Check PLAT751_ALERT_4_C Bond Calc 1.00000, Rep 1.0015(14) ...... Senseless s.u. N1 -H1A 1.555 1.555 ........ # 7 Check PLAT751_ALERT_4_C Bond Calc 0.79000, Rep 0.7932(11) ...... Senseless s.u. N1 -H1B 1.555 1.555 ........ # 8 Check PLAT751_ALERT_4_C Bond Calc 0.83000, Rep 0.8315(15) ...... Senseless s.u. N1 -H1C 1.555 1.555 ........ # 9 Check PLAT751_ALERT_4_C Bond Calc 0.97000, Rep 0.9703(12) ...... Senseless s.u. N2 -H2A 1.555 1.555 ........ # 11 Check PLAT751_ALERT_4_C Bond Calc 1.29000, Rep 1.2945(12) ...... Senseless s.u. O5 -H6A 1.555 1.555 ........ # 32 Check PLAT751_ALERT_4_C Bond Calc 1.18000, Rep 1.1837(11) ...... Senseless s.u. O6 -H6A 1.555 1.555 ........ # 34 Check PLAT752_ALERT_4_C Angle Calc 103.00, Rep 102.59(10) ...... Senseless s.u. C4 -N1 -H1A 1.555 1.555 1.555 # 5 Check PLAT752_ALERT_4_C Angle Calc 107.00, Rep 107.06(15) ...... Senseless s.u. C4 -N1 -H1B 1.555 1.555 1.555 # 6 Check PLAT752_ALERT_4_C Angle Calc 108.00, Rep 107.83(13) ...... Senseless s.u. C4 -N1 -H1C 1.555 1.555 1.555 # 7 Check PLAT752_ALERT_4_C Angle Calc 125.00, Rep 124.65(16) ...... Senseless s.u. H1A -N1 -H1B 1.555 1.555 1.555 # 8 Check PLAT752_ALERT_4_C Angle Calc 103.00, Rep 103.41(14) ...... Senseless s.u. H1A -N1 -H1C 1.555 1.555 1.555 # 9 Check PLAT752_ALERT_4_C Angle Calc 110.00, Rep 110.21(14) ...... Senseless s.u. H1B -N1 -H1C 1.555 1.555 1.555 # 10 Check PLAT752_ALERT_4_C Angle Calc 114.00, Rep 113.65(11) ...... Senseless s.u. S1 -N2 -H2A 1.555 1.555 1.555 # 12 Check PLAT752_ALERT_4_C Angle Calc 116.00, Rep 116.39(12) ...... Senseless s.u. C7 -N2 -H2A 1.555 1.555 1.555 # 13 Check PLAT752_ALERT_4_C Angle Calc 105.00, Rep 105.28(11) ...... Senseless s.u. C17 -O5 -H6A 1.555 1.555 1.555 # 46 Check PLAT752_ALERT_4_C Angle Calc 102.00, Rep 102.01(10) ...... Senseless s.u. C12 -O6 -H6A 1.555 1.555 1.555 # 47 Check PLAT752_ALERT_4_C Angle Calc 157.00, Rep 156.58(6) ...... Senseless s.u. O5 -H6A -O6 1.555 1.555 1.555 # 75 Check PLAT755_ALERT_4_C D-H Calc 1.00000, Rep 1.0015(14) ...... Senseless s.u. N1 -H1A 1.555 1.555 ........ # 49 Check PLAT755_ALERT_4_C D-H Calc 0.79000, Rep 0.7932(11) ...... Senseless s.u. N1 -H1B 1.555 1.555 ........ # 49 Check PLAT755_ALERT_4_C D-H Calc 0.83000, Rep 0.8315(15) ...... Senseless s.u. N1 -H1C 1.555 1.555 ........ # 49 Check PLAT755_ALERT_4_C D-H Calc 0.97000, Rep 0.9703(12) ...... Senseless s.u. N2 -H2A 1.555 1.555 ........ # 49 Check PLAT755_ALERT_4_C D-H Calc 1.29000, Rep 1.2945(12) ...... Senseless s.u. O5 -H6A 1.555 1.555 ........ # 49 Check PLAT755_ALERT_4_C D-H Calc 1.29000, Rep 1.2945(12) ...... Senseless s.u. O5 -H6A 1.555 1.555 ........ # 49 Check PLAT755_ALERT_4_C D-H Calc 1.18000, Rep 1.1837(11) ...... Senseless s.u. O6 -H6A 1.555 1.555 ........ # 49 Check PLAT755_ALERT_4_C D-H Calc 1.18000, Rep 1.1837(11) ...... Senseless s.u. O6 -H6A 1.555 1.555 ........ # 49 Check PLAT756_ALERT_4_C H...A Calc 2.07000, Rep 2.0683(10) ...... Senseless s.u. H1A -O6 1.555 2.576 ........ # 49 Check PLAT756_ALERT_4_C H...A Calc 2.29000, Rep 2.2920(11) ...... Senseless s.u. H1B -N3 1.555 2.676 ........ # 49 Check PLAT756_ALERT_4_C H...A Calc 1.83000, Rep 1.8318(14) ...... Senseless s.u. H1C -O4 1.555 2.676 ........ # 49 Check PLAT756_ALERT_4_C H...A Calc 1.84000, Rep 1.8440(10) ...... Senseless s.u. H2A -O5 1.555 1.555 ........ # 49 Check PLAT756_ALERT_4_C H...A Calc 1.18000, Rep 1.1837(11) ...... Senseless s.u. H6A -O6 1.555 1.555 ........ # 49 Check PLAT756_ALERT_4_C H...A Calc 1.93000, Rep 1.9326(15) ...... Senseless s.u. H6A -C12 1.555 1.555 ........ # 49 Check PLAT756_ALERT_4_C H...A Calc 1.29000, Rep 1.2945(12) ...... Senseless s.u. H6A -O5 1.555 1.555 ........ # 49 Check PLAT756_ALERT_4_C H...A Calc 2.05000, Rep 2.0485(15) ...... Senseless s.u. H6A -C17 1.555 1.555 ........ # 49 Check PLAT758_ALERT_4_C D-H..A Calc 163.00, Rep 162.64(9) ...... Senseless s.u. N2 -H2A -O5 1.555 1.555 1.555 # 75 Check PLAT758_ALERT_4_C D-H..A Calc 157.00, Rep 156.58(6) ...... Senseless s.u. O5 -H6A -O6 1.555 1.555 1.555 # 75 Check PLAT758_ALERT_4_C D-H..A Calc 115.00, Rep 115.40(6) ...... Senseless s.u. O5 -H6A -C12 1.555 1.555 1.555 # 75 Check PLAT758_ALERT_4_C D-H..A Calc 157.00, Rep 156.58(6) ...... Senseless s.u. O6 -H6A -O5 1.555 1.555 1.555 # 75 Check PLAT758_ALERT_4_C D-H..A Calc 119.00, Rep 119.42(7) ...... Senseless s.u. O6 -H6A -C17 1.555 1.555 1.555 # 75 Check
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 5 Report PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as mixed Check PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.001 Degree PLAT395_ALERT_2_G Deviating X-O-Y Angle From 120 for O3 108.9 Degree
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 42 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 38 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Datablock: VABZIJ

Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O3 --N2 . 7.6 s.u. PLAT772_ALERT_2_B Suspect O-H Bond in CIF: O1 --H7 .. 1.43 Ang.
Alert level C PLAT222_ALERT_3_C Non-Solv. Resd 1 H Uiso(max)/Uiso(min) Range 4.4 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 --N1 . 5.7 s.u. PLAT355_ALERT_3_C Long O-H (X0.82,N0.98A) O7 - H7 . 1.02 Ang. PLAT751_ALERT_4_C Bond Calc 1.43000, Rep 1.4329(9) ...... Senseless s.u. O1 -H7 1.555 1.555 ........ # 2 Check PLAT751_ALERT_4_C Bond Calc 1.02000, Rep 1.0191(9) ...... Senseless s.u. O7 -H7 1.555 1.555 ........ # 9 Check PLAT751_ALERT_4_C Bond Calc 0.97000, Rep 0.9729(11) ...... Senseless s.u. N3 -H1N3 1.555 1.555 ........ # 15 Check PLAT751_ALERT_4_C Bond Calc 0.91000, Rep 0.9085(11) ...... Senseless s.u. N4 -H1N4 1.555 1.555 ........ # 18 Check PLAT751_ALERT_4_C Bond Calc 0.92000, Rep 0.9169(10) ...... Senseless s.u. O1W -H2W1 1.555 1.555 ........ # 45 Check PLAT751_ALERT_4_C Bond Calc 0.91000, Rep 0.9146(10) ...... Senseless s.u. O1W -H1W1 1.555 1.555 ........ # 46 Check PLAT752_ALERT_4_C Angle Calc 97.00, Rep 96.54(8) ...... Senseless s.u. C1 -O1 -H7 1.555 1.555 1.555 # 1 Check PLAT752_ALERT_4_C Angle Calc 101.00, Rep 101.27(9) ...... Senseless s.u. C7 -O7 -H7 1.555 1.555 1.555 # 2 Check PLAT752_ALERT_4_C Angle Calc 118.00, Rep 118.37(11) ...... Senseless s.u. C10 -N3 -H1N3 1.555 1.555 1.555 # 10 Check PLAT752_ALERT_4_C Angle Calc 119.00, Rep 119.14(11) ...... Senseless s.u. C11 -N3 -H1N3 1.555 1.555 1.555 # 11 Check PLAT752_ALERT_4_C Angle Calc 117.00, Rep 116.55(11) ...... Senseless s.u. C8 -N4 -H1N4 1.555 1.555 1.555 # 13 Check PLAT752_ALERT_4_C Angle Calc 119.00, Rep 118.72(12) ...... Senseless s.u. C11 -N4 -H1N4 1.555 1.555 1.555 # 14 Check PLAT752_ALERT_4_C Angle Calc 110.00, Rep 110.00(10) ...... Senseless s.u. H2W1 -O1W -H1W1 1.555 1.555 1.555 # 72 Check PLAT752_ALERT_4_C Angle Calc 166.00, Rep 165.94(7) ...... Senseless s.u. O1 -H7 -O7 1.555 1.555 1.555 # 73 Check PLAT755_ALERT_4_C D-H Calc 0.97000, Rep 0.9729(11) ...... Senseless s.u. N3 -H1N3 1.555 1.555 ........ # 46 Check PLAT755_ALERT_4_C D-H Calc 0.91000, Rep 0.9085(11) ...... Senseless s.u. N4 -H1N4 1.555 1.555 ........ # 46 Check PLAT755_ALERT_4_C D-H Calc 0.92000, Rep 0.9169(10) ...... Senseless s.u. O1W -H2W1 1.555 1.555 ........ # 46 Check PLAT755_ALERT_4_C D-H Calc 0.91000, Rep 0.9146(10) ...... Senseless s.u. O1W -H1W1 1.555 1.555 ........ # 46 Check PLAT755_ALERT_4_C D-H Calc 1.02000, Rep 1.0191(9) ...... Senseless s.u. O7 -H7 1.555 1.555 ........ # 46 Check PLAT756_ALERT_4_C H...A Calc 1.75000, Rep 1.7539(9) ...... Senseless s.u. H1N3 -O6 1.555 2.566 ........ # 46 Check PLAT756_ALERT_4_C H...A Calc 1.84000, Rep 1.8401(10) ...... Senseless s.u. H1N4 -O1W 1.555 1.555 ........ # 46 Check PLAT756_ALERT_4_C H...A Calc 1.89000, Rep 1.8895(10) ...... Senseless s.u. H2W1 -O1 1.555 1.565 ........ # 46 Check PLAT756_ALERT_4_C H...A Calc 2.04000, Rep 2.0399(10) ...... Senseless s.u. H1W1 -O3 1.555 2.655 ........ # 46 Check PLAT756_ALERT_4_C H...A Calc 1.43000, Rep 1.4329(9) ...... Senseless s.u. H7 -O1 1.555 1.555 ........ # 46 Check PLAT758_ALERT_4_C D-H..A Calc 168.00, Rep 167.76(8) ...... Senseless s.u. N4 -H1N4 -O1W 1.555 1.555 1.555 # 73 Check PLAT758_ALERT_4_C D-H..A Calc 166.00, Rep 165.94(7) ...... Senseless s.u. O7 -H7 -O1 1.555 1.555 1.555 # 73 Check
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 5 Report PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as mixed Check PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.002 Degree PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 4 Note PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2018 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 2 ALERT level B = A potentially serious problem, consider carefully 29 ALERT level C = Check. Ensure it is not caused by an omission or oversight 8 ALERT level G = General information/check it is not something unexpected 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 28 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Datablock: WADXOR

Alert level C PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Explicit -P 2yab c PLAT230_ALERT_2_C Hirshfeld Test Diff for N3B --C3B . 5.9 s.u. PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of N3B Check PLAT410_ALERT_2_C Short Intra H...H Contact H12A ..H14A 1.96 Ang. x,y,z = 1_555 Check PLAT751_ALERT_4_C Bond Calc 0.96000, Rep 0.9604(17) ...... Senseless s.u. N8A -H8A 1.555 1.555 ........ # 31 Check PLAT752_ALERT_4_C Angle Calc 120.00, Rep 119.53(19) ...... Senseless s.u. C7A -N8A -H8A 1.555 1.555 1.555 # 39 Check PLAT755_ALERT_4_C D-H Calc 0.96000, Rep 0.9604(17) ...... Senseless s.u. N8A -H8A 1.555 1.555 ........ # 66 Check PLAT756_ALERT_4_C H...A Calc 1.93000, Rep 1.9329(15) ...... Senseless s.u. H8A -O11B 1.555 1.555 ........ # 66 Check PLAT758_ALERT_4_C D-H..A Calc 163.00, Rep 162.83(11) ...... Senseless s.u. N8A -H8A -O11B 1.555 1.555 1.555 # 151 Check PLAT772_ALERT_2_C Suspect O-H Bond in CIF: O21B --H21B .. 1.30 Ang. PLAT772_ALERT_2_C Suspect O-H Bond in CIF: O12B --H2B .. 1.38 Ang. PLAT776_ALERT_1_C Suspect D-H Dist in CIF: O12B --H2B .. 1.38 Ang.
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 3 Report PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT300_ALERT_4_G Atom Site Occupancy of H10A Constrained at 0.686 Check PLAT300_ALERT_4_G Atom Site Occupancy of H11A Constrained at 0.686 Check PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 6% Note PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 2 ) 18% Note PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd 2 26.63 Check PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd 3 0.69 Check PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd 4 0.69 Check PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 40 Check C9A -N8A -C13A 1.555 1.555 1.555 22.60 Deg. PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 2 Note PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2018 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 12 ALERT level C = Check. Ensure it is not caused by an omission or oversight 13 ALERT level G = General information/check it is not something unexpected 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 13 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Datablock: YAXPOE

Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O4 --N4 . 7.1 s.u. PLAT230_ALERT_2_B Hirshfeld Test Diff for O6 --C9 . 8.2 s.u.
Alert level C DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.25 Report PLAT097_ALERT_2_C Large Reported Max. (Positive) Residual Density 0.63 eA-3 PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 --C42 . 5.8 s.u. PLAT245_ALERT_2_C U(iso) H7 Smaller than U(eq) O7 by 0.021 Ang   2 PLAT751_ALERT_4_C Bond Calc 0.94000, Rep 0.9448(11) ...... Senseless s.u. N1 -H71 1.555 1.555 ........ # 1 Check PLAT751_ALERT_4_C Bond Calc 0.92000, Rep 0.9238(15) ...... Senseless s.u. O7 -H7 1.555 1.555 ........ # 73 Check PLAT752_ALERT_4_C Angle Calc 110.00, Rep 109.70(10) ...... Senseless s.u. H71 -N1 -C3 1.555 1.555 1.555 # 1 Check PLAT752_ALERT_4_C Angle Calc 107.00, Rep 107.37(11) ...... Senseless s.u. H71 -N1 -C4 1.555 1.555 1.555 # 2 Check PLAT752_ALERT_4_C Angle Calc 107.00, Rep 106.90(11) ...... Senseless s.u. H71 -N1 -C7 1.555 1.555 1.555 # 3 Check PLAT752_ALERT_4_C Angle Calc 102.00, Rep 101.64(10) ...... Senseless s.u. C41 -O1 -H7 1.555 1.555 1.555 # 106 Check PLAT752_ALERT_4_C Angle Calc 113.00, Rep 112.68(16) ...... Senseless s.u. C9 -O7 -H7 1.555 1.555 1.555 # 107 Check PLAT752_ALERT_4_C Angle Calc 149.00, Rep 148.96(9) ...... Senseless s.u. O1 -H7 -O7 1.555 1.555 1.555 # 135 Check PLAT755_ALERT_4_C D-H Calc 0.94000, Rep 0.9448(11) ...... Senseless s.u. N1 -H71 1.555 1.555 ........ # 84 Check PLAT755_ALERT_4_C D-H Calc 0.94000, Rep 0.9448(11) ...... Senseless s.u. N1 -H71 1.555 1.555 ........ # 84 Check PLAT755_ALERT_4_C D-H Calc 0.92000, Rep 0.9238(15) ...... Senseless s.u. O7 -H7 1.555 1.555 ........ # 84 Check PLAT755_ALERT_4_C D-H Calc 0.92000, Rep 0.9238(15) ...... Senseless s.u. O7 -H7 1.555 1.555 ........ # 84 Check PLAT756_ALERT_4_C H...A Calc 1.95000, Rep 1.9544(11) ...... Senseless s.u. H71 -O1 1.555 3.666 ........ # 84 Check PLAT756_ALERT_4_C H...A Calc 2.30000, Rep 2.3020(16) ...... Senseless s.u. H71 -O2 1.555 3.666 ........ # 84 Check PLAT756_ALERT_4_C H...A Calc 1.67000, Rep 1.6675(13) ...... Senseless s.u. H7 -O1 1.555 1.555 ........ # 84 Check PLAT756_ALERT_4_C H...A Calc 2.30000, Rep 2.2985(16) ...... Senseless s.u. H7 -C41 1.555 1.555 ........ # 84 Check PLAT758_ALERT_4_C D-H..A Calc 149.00, Rep 148.96(9) ...... Senseless s.u. O7 -H7 -O1 1.555 1.555 1.555 # 135 Check PLAT758_ALERT_4_C D-H..A Calc 116.00, Rep 115.91(9) ...... Senseless s.u. O7 -H7 -C41 1.555 1.555 1.555 # 135 Check
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as mixed Check PLAT432_ALERT_2_G Short Inter X...Y Contact C35 ..C35 3.16 Ang. -x,1-y,-z = 3_565 Check PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2018 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 2 ALERT level B = A potentially serious problem, consider carefully 23 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 19 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL022_ALERT_1_A There is a mismatched ~ on line 249 180\% (Jeffrey, 1995). The O~carboxylate/carboxylicgroup~ ...O~hydroxy/oxo If you require a ~ then it should be escaped with a \, i.e. \~ Otherwise there must be a matching closing ~, e.g. C~2~H~4~ PUBL022_ALERT_1_A There is a mismatched ~ on line 250 group~ distance can be as short as 2.41 \%A in some If you require a ~ then it should be escaped with a \, i.e. \~ Otherwise there must be a matching closing ~, e.g. C~2~H~4~ PUBL022_ALERT_1_A There is a mismatched ~ on line 619 <0.06--0.10> \%A, <i>i.e.</i> for the shortest distances of <i>D</i>13 (\~ If you require a ~ then it should be escaped with a \, i.e. \~ Otherwise there must be a matching closing ~, e.g. C~2~H~4~
3 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: SMART (Bruker, 1997) for DUJZAK; SMART (Bruker, 1999) for JEVNAA; CAD-4 Software (Enraf-Nonius, 1989) for LUDFUL; APEX2 (Bruker, 2009) for NUQVEB, VABZIJ; SMART (Bruker, 2001) for QIQJAD; SMART (Bruker, 2007) for SAFGUD; SMART (Bruker, 2002) for SEDKET; CrysAlis PRO (Agilent, 2012) for TIYZIM; APEX2 (Bruker, 2004) for TUJPEV; CrysAlis PRO (Agilent, 2014) for WADXOR; APEX2 (Bruker, 2010) for YAXPOE. Cell refinement: SAINT (Bruker, 1997) for DUJZAK; SAINT (Bruker, 1999) for JEVNAA; CAD-4 Software (Enraf-Nonius, 1989) for LUDFUL; SAINT (Bruker, 2009) for NUQVEB, VABZIJ; SAINT (Bruker, 2001) for QIQJAD; SAINT (Bruker, 2007) for SAFGUD; SAINT (Bruker, 2002) for SEDKET; CrysAlis PRO (Agilent, 2012) for TIYZIM; SAINT (Bruker, 2004) for TUJPEV; CrysAlis PRO (Agilent, 2014) for WADXOR; SAINT (Bruker, 2010) for YAXPOE. Data reduction: SAINT (Bruker, 1997) for DUJZAK; SAINT (Bruker, 1999) for JEVNAA; Xtal3.5 (Hall et al., 1995) for LUDFUL; SAINT (Bruker, 2009) for NUQVEB, VABZIJ; SAINT (Bruker, 2001) for QIQJAD; SAINT (Bruker, 2007) for SAFGUD; SAINT (Bruker, 2002) for SEDKET; CrysAlis RED (Agilent, 2012) for TIYZIM; SAINT (Bruker, 2004) for TUJPEV; CrysAlis PRO (Agilent, 2014) for WADXOR; SAINT (Bruker, 2010) for YAXPOE. Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for DUJZAK, JEVNAA, LUDFUL, QIQJAD, SEDKET, TUJPEV, YAXPOE; SHELXTL (Sheldrick, 2008) for NUQVEB, VABZIJ; SHELXS-97 (Sheldrick, 2008) for SAFGUD; SUPERFLIP (Palatinus & Chapuis, 2007) for TIYZIM; SIR92 (Altomare et al., 1993) for WADXOR. Program(s) used to refine structure: JANA2016 (Petricek et al., 2014) for DUJZAK; JANA2006 (Petricek et al., 2014) for JEVNAA, LUDFUL, NUQVEB, QIQJAD, SAFGUD, TIYZIM, TUJPEV, VABZIJ, YAXPOE; JANA2006 (Petricek, 2014) for SEDKET.

Bis(quinolin-8-ol)silver(I) 2-hydroxy-3,5-dinitrobenzoate (DUJZAK) top
Crystal data top
[Ag(C9H7NO)2](C7H3N2O7)F(000) = 628
Mr = 625.30Dx = 1.823 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4356 reflections
a = 9.0154 (18) Åθ = 3.6–27.6°
b = 7.6122 (15) ŵ = 0.95 mm1
c = 17.138 (3) ÅT = 293 K
β = 104.38 (3)°Block, yellow
V = 1139.3 (4) Å30.20 × 0.15 × 0.11 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
4225 reflections with I > 3σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 27.6°, θmin = 3.6°
φ and ω scansh = 1111
10841 measured reflectionsk = 98
4602 independent reflectionsl = 2222
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F > 3σ(F)] = 0.023Hydrogen site location: difference Fourier map
wR(F) = 0.053H atoms treated by a mixture of independent and constrained refinement
S = 1.34Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
4602 reflections(Δ/σ)max = 0.025
356 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.30 e Å3
48 constraintsAbsolute structure: 1800 of Friedel pairs used in the refinement
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.004 (17)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Number of fixed parameters 9.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.062197 (18)0.74282 (3)0.668863 (11)0.01868 (5)
O10.0993 (2)0.4630 (2)0.64021 (12)0.0202 (6)
O20.1741 (2)0.5061 (2)0.77196 (12)0.0214 (6)
N10.1154 (2)0.7667 (3)0.55616 (13)0.0177 (7)
N20.2685 (2)0.8371 (3)0.75427 (14)0.0163 (7)
C10.1280 (3)0.9181 (4)0.51463 (18)0.0222 (9)
H1a0.0612411.0092760.5353860.0267*
C20.2362 (3)0.9448 (4)0.44205 (18)0.0243 (9)
H2a0.2409231.0519170.4154390.0291*
C30.3354 (3)0.8130 (4)0.41016 (19)0.0209 (9)
H3a0.4078480.8294710.3616120.0251*
C40.3270 (3)0.6506 (4)0.45167 (18)0.0169 (8)
C50.4264 (3)0.5079 (4)0.42259 (17)0.0209 (9)
H5a0.5007440.5183440.374290.0251*
C60.4131 (3)0.3554 (4)0.46539 (17)0.0217 (9)
H6a0.4774020.2616620.4453110.026*
C70.3036 (3)0.3371 (3)0.53948 (17)0.0184 (8)
H7a0.2979650.2326720.5682040.0221*
C80.2057 (3)0.4717 (3)0.56954 (16)0.0148 (8)
C90.2139 (3)0.6331 (3)0.52566 (16)0.0141 (8)
C100.3159 (3)0.9993 (4)0.74633 (17)0.0188 (9)
H10a0.2568921.0698720.7061080.0225*
C110.4512 (3)1.0703 (4)0.79567 (18)0.0220 (9)
H11a0.4808851.1845290.7877030.0264*
C120.5373 (3)0.9693 (4)0.85495 (18)0.0210 (9)
H12a0.6273461.013970.8877960.0252*
C130.4907 (3)0.7960 (3)0.86712 (16)0.0171 (8)
C140.5743 (3)0.6845 (4)0.92853 (17)0.0200 (8)
H14a0.6650830.7239380.9627490.024*
C150.5225 (3)0.5197 (4)0.93771 (17)0.0206 (8)
H15a0.5777890.4478070.9785390.0247*
C160.3863 (3)0.4570 (3)0.88620 (16)0.0173 (8)
H16a0.351780.3446690.89370.0208*
C170.3043 (3)0.5596 (3)0.82528 (16)0.0142 (8)
C180.3541 (2)0.7340 (5)0.81443 (13)0.0140 (6)
O30.1402 (2)0.0134 (3)0.92525 (13)0.0259 (7)
O40.4152 (2)0.3755 (3)0.69139 (13)0.0284 (7)
O50.3271 (2)0.5961 (3)0.76858 (13)0.0271 (7)
O60.1238 (2)0.5247 (2)0.98352 (12)0.0211 (6)
O70.1679 (2)0.2659 (4)1.03546 (11)0.0286 (6)
O80.0981 (2)0.1498 (2)0.70180 (12)0.0237 (7)
O90.06657 (19)0.2138 (2)0.81885 (11)0.0196 (6)
N30.3217 (2)0.4436 (3)0.74764 (14)0.0173 (7)
N40.1088 (2)0.3645 (3)0.98085 (13)0.0152 (7)
C190.1970 (3)0.3339 (4)0.79254 (18)0.0130 (8)
C200.1027 (3)0.3992 (3)0.86303 (15)0.0126 (7)
H20a0.1149340.5128550.8802950.0151*
C210.0095 (2)0.2908 (3)0.90660 (15)0.0114 (8)
C220.0326 (3)0.1188 (3)0.88194 (16)0.0130 (8)
C230.0605 (3)0.0603 (3)0.80708 (16)0.0129 (7)
C240.1770 (3)0.1678 (3)0.76332 (17)0.0132 (8)
H24a0.2405390.1286610.7150890.0159*
C250.0307 (3)0.1145 (3)0.77245 (16)0.0148 (8)
H1aa0.0914070.3777320.6638150.047 (14)*
H2aa0.1455360.3950040.7839010.043 (11)*
H3b0.1352790.0953530.8879930.17 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.01622 (8)0.01722 (9)0.01945 (10)0.00339 (11)0.00154 (6)0.00024 (11)
O10.0219 (9)0.0127 (9)0.0199 (10)0.0063 (8)0.0065 (8)0.0058 (8)
O20.0185 (9)0.0173 (9)0.0231 (11)0.0065 (8)0.0049 (8)0.0030 (8)
N10.0190 (9)0.0152 (14)0.0181 (11)0.0003 (11)0.0033 (8)0.0008 (10)
N20.0145 (10)0.0161 (11)0.0187 (12)0.0018 (9)0.0049 (9)0.0005 (9)
C10.0254 (14)0.0145 (12)0.0263 (16)0.0042 (12)0.0056 (12)0.0044 (11)
C20.0325 (15)0.0177 (13)0.0239 (16)0.0069 (13)0.0093 (12)0.0104 (11)
C30.0214 (13)0.0247 (13)0.0154 (15)0.0059 (12)0.0021 (12)0.0023 (11)
C40.0136 (12)0.0220 (14)0.0150 (15)0.0026 (11)0.0031 (10)0.0005 (12)
C50.0160 (12)0.0289 (15)0.0156 (14)0.0005 (12)0.0002 (10)0.0035 (12)
C60.0156 (12)0.0247 (14)0.0217 (16)0.0092 (12)0.0009 (11)0.0062 (11)
C70.0179 (12)0.0175 (14)0.0187 (14)0.0039 (11)0.0026 (10)0.0018 (11)
C80.0139 (12)0.0146 (12)0.0140 (13)0.0001 (11)0.0000 (9)0.0001 (10)
C90.0147 (12)0.0142 (12)0.0132 (13)0.0002 (11)0.0032 (9)0.0016 (10)
C100.0208 (13)0.0176 (13)0.0198 (15)0.0021 (12)0.0084 (11)0.0021 (11)
C110.0259 (14)0.0166 (13)0.0254 (16)0.0085 (12)0.0099 (12)0.0039 (11)
C120.0180 (12)0.0226 (14)0.0235 (15)0.0108 (12)0.0074 (11)0.0101 (12)
C130.0138 (11)0.0232 (14)0.0156 (14)0.0032 (10)0.0064 (10)0.0059 (10)
C140.0118 (11)0.0285 (14)0.0182 (15)0.0034 (11)0.0010 (10)0.0071 (10)
C150.0143 (12)0.0281 (15)0.0175 (15)0.0038 (12)0.0002 (10)0.0017 (11)
C160.0160 (12)0.0146 (12)0.0208 (15)0.0018 (11)0.0035 (10)0.0001 (10)
C170.0107 (11)0.0149 (12)0.0165 (14)0.0020 (10)0.0025 (9)0.0031 (10)
C180.0115 (9)0.0160 (11)0.0156 (11)0.0014 (17)0.0052 (8)0.0001 (15)
O30.0215 (10)0.0236 (11)0.0279 (12)0.0066 (9)0.0029 (9)0.0016 (9)
O40.0212 (10)0.0283 (11)0.0267 (12)0.0044 (9)0.0110 (8)0.0010 (9)
O50.0295 (10)0.0195 (10)0.0288 (12)0.0130 (9)0.0004 (9)0.0016 (9)
O60.0213 (9)0.0158 (9)0.0236 (11)0.0028 (8)0.0007 (8)0.0059 (8)
O70.0340 (9)0.0225 (9)0.0194 (9)0.0057 (15)0.0121 (7)0.0015 (13)
O80.0304 (11)0.0156 (10)0.0204 (11)0.0061 (9)0.0028 (8)0.0051 (8)
O90.0209 (8)0.0129 (12)0.0223 (10)0.0061 (8)0.0003 (7)0.0009 (8)
N30.0141 (10)0.0190 (11)0.0169 (12)0.0064 (10)0.0001 (9)0.0044 (9)
N40.0115 (10)0.0169 (11)0.0154 (12)0.0012 (9)0.0003 (8)0.0025 (9)
C190.0080 (11)0.0164 (12)0.0135 (15)0.0043 (10)0.0009 (10)0.0044 (11)
C200.0158 (12)0.0082 (11)0.0137 (13)0.0009 (10)0.0036 (9)0.0004 (9)
C210.0098 (9)0.0122 (17)0.0103 (11)0.0048 (10)0.0012 (8)0.0021 (9)
C220.0086 (11)0.0150 (13)0.0147 (14)0.0009 (10)0.0015 (9)0.0033 (10)
C230.0133 (11)0.0110 (12)0.0134 (13)0.0001 (10)0.0015 (9)0.0007 (9)
C240.0120 (12)0.0135 (13)0.0142 (15)0.0018 (11)0.0033 (10)0.0004 (11)
C250.0153 (12)0.0109 (11)0.0177 (14)0.0006 (10)0.0029 (10)0.0010 (10)
Geometric parameters (Å, º) top
O1—C81.347 (3)C13—C141.415 (4)
O1—H1aa0.7585 (19)C13—C181.415 (3)
O2—C171.359 (3)C14—H14a0.93
O2—H2aa0.922 (2)C14—C151.361 (4)
N1—C11.344 (4)C15—H15a0.93
N1—C91.365 (3)C15—C161.406 (3)
N2—C101.325 (4)C16—H16a0.93
N2—C181.371 (4)C16—C171.365 (4)
C1—H1a0.93C17—C181.429 (5)
C1—C21.392 (4)O3—C221.333 (3)
C2—H2a0.93O3—H3b1.040 (2)
C2—C31.364 (4)O4—N31.227 (3)
C3—H3a0.93O5—N31.219 (3)
C3—C41.419 (4)O6—N41.226 (3)
C4—C51.418 (4)O7—N41.215 (3)
C4—C91.423 (4)O8—C251.242 (3)
C5—H5a0.93O9—C251.275 (3)
C5—C61.362 (4)O9—H3b1.4952 (19)
C6—H6a0.93N3—C191.458 (3)
C6—C71.408 (4)N4—C211.473 (3)
C7—H7a0.93C19—C201.385 (4)
C7—C81.367 (4)C19—C241.388 (4)
C8—C91.433 (4)C20—H20a0.93
C10—H10a0.93C20—C211.373 (3)
C10—C111.408 (4)C21—C221.408 (4)
C11—H11a0.93C22—C231.419 (3)
C11—C121.354 (4)C23—C241.394 (3)
C12—H12a0.93C23—C251.508 (4)
C12—C131.416 (4)C24—H24a0.93
C8—O1—H1aa118.2 (2)C13—C14—C15120.2 (2)
C17—O2—H2aa111.60 (19)H14a—C14—C15119.88
C1—N1—C9118.3 (2)C14—C15—H15a119.61
C10—N2—C18118.4 (2)C14—C15—C16120.8 (2)
N1—C1—H1a118.43H15a—C15—C16119.61
N1—C1—C2123.1 (2)C15—C16—H16a119.71
H1a—C1—C2118.43C15—C16—C17120.6 (2)
C1—C2—H2a120.19H16a—C16—C17119.71
C1—C2—C3119.6 (3)O2—C17—C16123.8 (2)
H2a—C2—C3120.19O2—C17—C18116.0 (2)
C2—C3—H3a120.26C16—C17—C18120.2 (2)
C2—C3—C4119.5 (2)N2—C18—C13121.8 (3)
H3a—C3—C4120.27N2—C18—C17119.6 (2)
C3—C4—C5122.8 (2)C13—C18—C17118.6 (2)
C3—C4—C9117.8 (2)C22—O3—H3b102.89 (19)
C5—C4—C9119.5 (2)C25—O9—H3b102.84 (17)
C4—C5—H5a120O4—N3—O5124.3 (2)
C4—C5—C6120.0 (2)O4—N3—C19117.5 (2)
H5a—C5—C6120O5—N3—C19118.2 (2)
C5—C6—H6a119.4O6—N4—O7124.2 (2)
C5—C6—C7121.2 (2)O6—N4—C21116.66 (19)
H6a—C6—C7119.4O7—N4—C21119.1 (2)
C6—C7—H7a119.72N3—C19—C20118.7 (2)
C6—C7—C8120.6 (2)N3—C19—C24118.9 (2)
H7a—C7—C8119.72C20—C19—C24122.3 (2)
O1—C8—C7123.5 (2)C19—C20—H20a121.04
O1—C8—C9116.5 (2)C19—C20—C21117.9 (2)
C7—C8—C9120.0 (2)H20a—C20—C21121.04
N1—C9—C4121.7 (2)N4—C21—C20116.7 (2)
N1—C9—C8119.6 (2)N4—C21—C22120.67 (19)
C4—C9—C8118.7 (2)C20—C21—C22122.7 (2)
N2—C10—H10a118.33O3—C22—C21122.3 (2)
N2—C10—C11123.3 (2)O3—C22—C23120.0 (2)
H10a—C10—C11118.33C21—C22—C23117.7 (2)
C10—C11—H11a120.58C22—C23—C24120.0 (2)
C10—C11—C12118.8 (3)C22—C23—C25120.6 (2)
H11a—C11—C12120.58C24—C23—C25119.4 (2)
C11—C12—H12a119.87C19—C24—C23119.2 (2)
C11—C12—C13120.3 (2)C19—C24—H24a120.38
H12a—C12—C13119.87C23—C24—H24a120.38
C12—C13—C14123.1 (2)O8—C25—O9125.0 (2)
C12—C13—C18117.4 (2)O8—C25—C23118.9 (2)
C14—C13—C18119.6 (3)O9—C25—C23116.1 (2)
C13—C14—H14a119.88O3—H3b—O9155.88 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11a···O5i0.932.483.335 (4)152
O1—H1aa···O80.7585 (19)1.859 (2)2.606 (3)167.96 (14)
O2—H2aa···O90.922 (2)1.727 (2)2.631 (3)166.48 (15)
O3—H3b···O91.040 (2)1.4952 (19)2.481 (3)155.88 (12)
Symmetry code: (i) x+1, y+2, z.
Tetrakis(1H-imidazole-κN3)zinc(II) bis(2-hydroxy-3,5-dinitrobenzoate) (JEVNAA) top
Crystal data top
[Zn(C3H4N2)4](C7H3N2O7)2F(000) = 1616
Mr = 791.93Dx = 1.664 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3242 reflections
a = 25.0809 (15) Åθ = 2.1–26.9°
b = 6.7251 (4) ŵ = 0.87 mm1
c = 18.9145 (10) ÅT = 293 K
β = 97.658 (6)°Platelet, yellow
V = 3161.9 (3) Å30.20 × 0.18 × 0.10 mm
Z = 4
Data collection top
Bruker APEX-II area-detector
diffractometer
3635 independent reflections
Radiation source: fine-focus sealed tube2152 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.058
φ and ω scansθmax = 27.6°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 3231
Tmin = 0.846, Tmax = 0.918k = 88
20634 measured reflectionsl = 2424
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F > 3σ(F)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F) = 0.075Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
S = 1.23(Δ/σ)max = 0.007
3635 reflectionsΔρmax = 0.23 e Å3
244 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
32 constraintsExtinction coefficient: 1400 (500)
Primary atom site location: structure-invariant direct methods
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Number of fixed parameters: 9

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.47960 (10)0.4200 (3)0.62639 (13)0.0460 (10)
H10.4440040.3982020.6330960.0552*
C20.50386 (10)0.3369 (4)0.57533 (13)0.0484 (10)
H20.4887450.2482950.5405650.0581*
C30.56018 (9)0.5299 (3)0.63970 (12)0.0401 (9)
H30.5915910.5978190.6566660.0481*
C40.59325 (9)0.9065 (4)0.83991 (12)0.0404 (9)
H40.5917220.8232290.878850.0485*
N40.62879 (7)1.0508 (3)0.83789 (11)0.0471 (8)
C60.57665 (9)1.0451 (4)0.73735 (13)0.0444 (9)
H60.5609521.0747050.6911990.0533*
C70.73999 (9)0.4553 (3)0.34225 (11)0.0329 (8)
C80.79245 (9)0.5059 (3)0.36676 (12)0.0342 (8)
H80.8176390.517620.3350920.0411*
C90.80717 (8)0.5388 (3)0.43803 (12)0.0311 (8)
C100.77048 (8)0.5210 (3)0.48978 (12)0.0302 (8)
C110.71702 (8)0.4593 (3)0.46099 (11)0.0282 (7)
C120.70286 (9)0.4300 (3)0.38898 (12)0.0323 (8)
H120.6678450.3926760.3716560.0388*
C130.67545 (9)0.4249 (3)0.50834 (12)0.0333 (8)
N10.51487 (7)0.5429 (3)0.66784 (9)0.0373 (7)
N20.55523 (8)0.4075 (3)0.58408 (10)0.0438 (8)
N30.56024 (7)0.8957 (3)0.77961 (9)0.0354 (7)
C50.61854 (9)1.1406 (4)0.77303 (14)0.0479 (10)
H50.6370641.2474020.756750.0575*
N50.72386 (8)0.4225 (3)0.26644 (10)0.0427 (8)
N60.86351 (7)0.5897 (3)0.46068 (11)0.0403 (8)
O10.78238 (6)0.5518 (2)0.55681 (8)0.0378 (6)
O20.68832 (6)0.4695 (2)0.57640 (8)0.0420 (6)
O30.63104 (6)0.3579 (2)0.48669 (8)0.0426 (6)
O40.67630 (7)0.3835 (3)0.24643 (8)0.0575 (7)
O50.75772 (7)0.4340 (3)0.22570 (9)0.0662 (8)
O60.89634 (7)0.5475 (3)0.42013 (9)0.0658 (8)
O70.87622 (6)0.6730 (3)0.51757 (9)0.0568 (7)
Zn10.50.70908 (6)0.750.03866 (15)
H1a0.7286410.5082680.5793350.108 (11)*
H2a0.5806680.3677140.5525620.088 (9)*
H4a0.6575931.0985790.8705940.106 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0323 (14)0.0558 (17)0.0507 (17)0.0069 (12)0.0086 (12)0.0071 (13)
C20.0460 (16)0.0536 (18)0.0448 (17)0.0064 (13)0.0033 (12)0.0116 (13)
C30.0327 (13)0.0485 (16)0.0396 (16)0.0053 (11)0.0071 (11)0.0037 (12)
C40.0366 (14)0.0491 (16)0.0343 (15)0.0066 (12)0.0004 (11)0.0062 (12)
N40.0332 (12)0.0568 (15)0.0484 (15)0.0016 (10)0.0048 (10)0.0044 (11)
C60.0416 (15)0.0568 (17)0.0336 (15)0.0015 (12)0.0004 (12)0.0077 (13)
C70.0344 (13)0.0369 (14)0.0264 (14)0.0024 (10)0.0002 (10)0.0008 (10)
C80.0332 (13)0.0366 (14)0.0337 (15)0.0009 (10)0.0073 (10)0.0030 (10)
C90.0254 (12)0.0287 (13)0.0382 (15)0.0031 (9)0.0003 (10)0.0001 (10)
C100.0338 (13)0.0219 (12)0.0342 (14)0.0035 (9)0.0013 (10)0.0006 (10)
C110.0288 (12)0.0245 (12)0.0310 (14)0.0011 (9)0.0030 (10)0.0013 (10)
C120.0281 (12)0.0306 (14)0.0370 (15)0.0009 (9)0.0002 (10)0.0004 (10)
C130.0338 (13)0.0312 (14)0.0356 (15)0.0037 (10)0.0067 (11)0.0026 (10)
N10.0341 (11)0.0433 (13)0.0357 (12)0.0029 (9)0.0086 (9)0.0001 (9)
N20.0437 (12)0.0526 (14)0.0371 (13)0.0034 (10)0.0126 (10)0.0035 (10)
N30.0321 (10)0.0442 (12)0.0288 (11)0.0016 (9)0.0003 (9)0.0042 (9)
C50.0393 (15)0.0540 (18)0.0499 (18)0.0090 (12)0.0040 (12)0.0069 (14)
N50.0414 (13)0.0517 (14)0.0338 (13)0.0032 (10)0.0004 (10)0.0005 (10)
N60.0327 (11)0.0435 (13)0.0438 (14)0.0038 (9)0.0023 (10)0.0059 (10)
O10.0362 (9)0.0445 (10)0.0308 (10)0.0009 (7)0.0026 (7)0.0054 (7)
O20.0399 (10)0.0552 (11)0.0313 (10)0.0055 (8)0.0056 (7)0.0066 (8)
O30.0325 (9)0.0561 (11)0.0400 (10)0.0091 (8)0.0079 (7)0.0084 (8)
O40.0395 (10)0.0890 (14)0.0408 (11)0.0047 (9)0.0063 (8)0.0048 (9)
O50.0499 (11)0.1146 (17)0.0361 (11)0.0057 (10)0.0133 (9)0.0036 (10)
O60.0351 (10)0.1012 (16)0.0635 (13)0.0075 (10)0.0156 (9)0.0121 (11)
O70.0430 (10)0.0799 (14)0.0453 (11)0.0182 (9)0.0029 (8)0.0108 (10)
Zn10.0355 (2)0.0455 (3)0.0352 (3)00.00566 (17)0
Geometric parameters (Å, º) top
C1—H10.93C8—H80.93
C1—C21.331 (4)C8—C91.367 (3)
C1—N11.377 (3)C9—C101.435 (3)
C2—H20.93C9—N61.462 (3)
C2—N21.362 (3)C10—C111.440 (3)
C3—H30.93C10—O11.280 (3)
C3—N11.320 (3)C11—C121.375 (3)
C3—N21.328 (3)C11—C131.480 (3)
C4—H40.93C12—H120.93
C4—N41.322 (3)C13—O21.319 (3)
C4—N31.319 (3)C13—O31.220 (3)
N4—C51.361 (3)N2—H2a0.967 (2)
N4—H4a0.9427 (18)C5—H50.93
C6—H60.93N5—O41.231 (3)
C6—N31.381 (3)N5—O51.223 (3)
C6—C51.335 (3)N6—O61.231 (3)
C7—C81.378 (3)N6—O71.217 (3)
C7—C121.377 (3)O1—H1a1.4955 (15)
C7—N51.454 (3)O2—H1a1.0386 (15)
H1—C1—C2124.94C9—C10—O1125.18 (18)
H1—C1—N1124.94C11—C10—O1120.2 (2)
C2—C1—N1110.1 (2)C10—C11—C12121.4 (2)
C1—C2—H2126.81C10—C11—C13120.78 (19)
C1—C2—N2106.4 (2)C12—C11—C13117.85 (18)
H2—C2—N2126.81C7—C12—C11120.69 (19)
H3—C3—N1124.28C7—C12—H12119.65
H3—C3—N2124.28C11—C12—H12119.66
N1—C3—N2111.44 (19)C11—C13—O2117.03 (18)
H4—C4—N4124.35C11—C13—O3122.6 (2)
H4—C4—N3124.35O2—C13—O3120.3 (2)
N4—C4—N3111.3 (2)C1—N1—C3104.66 (19)
C4—N4—C5107.74 (19)C2—N2—C3107.4 (2)
C4—N4—H4a133.8 (2)C2—N2—H2a121.3 (2)
C5—N4—H4a118.5 (2)C3—N2—H2a131.3 (2)
H6—C6—N3125.29C4—N3—C6105.04 (18)
H6—C6—C5125.29N4—C5—C6106.5 (2)
N3—C6—C5109.4 (2)N4—C5—H5126.75
C8—C7—C12120.8 (2)C6—C5—H5126.75
C8—C7—N5119.8 (2)C7—N5—O4117.82 (19)
C12—C7—N5119.40 (19)C7—N5—O5119.10 (18)
C7—C8—H8120.27O4—N5—O5123.08 (19)
C7—C8—C9119.5 (2)C9—N6—O6117.66 (19)
H8—C8—C9120.27C9—N6—O7119.73 (19)
C8—C9—C10123.06 (18)O6—N6—O7122.61 (18)
C8—C9—N6116.8 (2)C10—O1—H1a98.67 (13)
C10—C9—N6120.16 (19)C13—O2—H1a102.66 (16)
C9—C10—C11114.56 (19)O1—H1a—O2160.37 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O3i0.932.473.327 (3)154
O2—H1a···C101.0386 (15)2.110 (2)2.820 (3)123.5 (1)
O2—H1a···O11.0386 (15)1.4955 (15)2.498 (2)160.4 (1)
N2—H2a···O30.967 (2)1.8902 (16)2.838 (3)165.87 (12)
N4—H4a···O1ii0.9427 (18)1.9236 (14)2.784 (2)150.60 (13)
N4—H4a···O7ii0.9427 (18)2.4336 (18)2.873 (3)108.36 (13)
Symmetry codes: (i) x, y+1, z+1/2; (ii) x+3/2, y+1/2, z+3/2.
3,5-Dinitrosalicylic acid–phenazine (1/1) (LUDFUL) top
Crystal data top
C7H4N2O7·C12H8N2Dx = 1.556 Mg m3
Mr = 408.33Melting point: 471 K
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
a = 14.8002 (15) ÅCell parameters from 25 reflections
b = 7.4029 (16) Åθ = 5–12°
c = 16.0091 (16) ŵ = 0.12 mm1
β = 96.395 (8)°T = 293 K
V = 1743.1 (5) Å3Rhombic, yellow
Z = 40.36 × 0.34 × 0.26 mm
F(000) = 840
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.056
Radiation source: fine-focus sealed tubeθmax = 28.0°, θmin = 1.5°
Graphite monochromatorh = 019
w scansk = 99
8396 measured reflectionsl = 2121
4202 independent reflections3 standard reflections every 150 reflections
1587 reflections with I > 3σ(I) intensity decay: 2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F > 3σ(F)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F) = 0.083Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
S = 1.08(Δ/σ)max = 0.006
4202 reflectionsΔρmax = 0.29 e Å3
274 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
40 constraintsExtinction coefficient: 5100 (500)
Primary atom site location: structure-invariant direct methods
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Number of fixed parameters: 6

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O30.98761 (10)0.2874 (2)0.46747 (9)0.0599 (6)
O10.85079 (8)0.4309 (2)0.24121 (9)0.0539 (6)
C10.98636 (12)0.4161 (3)0.33159 (12)0.0373 (7)
O71.12739 (10)0.6537 (3)0.15665 (10)0.0716 (7)
C41.17200 (13)0.4785 (3)0.36328 (13)0.0421 (8)
H4a1.2340710.5010180.3734320.0506*
C51.12429 (13)0.5256 (3)0.28746 (12)0.0378 (7)
O20.84456 (9)0.3110 (2)0.36758 (9)0.0632 (7)
C21.03254 (14)0.3661 (3)0.40995 (13)0.0430 (8)
C31.12654 (13)0.3980 (3)0.42348 (12)0.0423 (8)
N11.18089 (15)0.3455 (3)0.50174 (12)0.0665 (9)
C70.88704 (14)0.3818 (3)0.31414 (14)0.0457 (9)
C61.03232 (13)0.4947 (3)0.27113 (12)0.0386 (7)
H6a1.0015060.5268820.2194650.0463*
O61.25212 (10)0.6448 (3)0.23814 (10)0.0804 (8)
O41.14445 (14)0.2742 (3)0.55587 (13)0.1291 (12)
N21.17129 (12)0.6128 (3)0.22290 (12)0.0504 (8)
O51.26041 (12)0.3839 (3)0.51002 (10)0.0996 (10)
N30.68389 (10)0.3729 (2)0.18982 (10)0.0388 (6)
N40.50803 (11)0.3575 (3)0.10509 (11)0.0517 (7)
C170.57960 (14)0.2988 (3)0.06927 (13)0.0505 (9)
C190.61248 (13)0.4326 (3)0.22726 (12)0.0377 (7)
C80.74378 (15)0.2489 (3)0.06912 (15)0.0552 (9)
H8a0.8026870.2529570.0962150.0663*
C160.66987 (13)0.3064 (3)0.11118 (13)0.0405 (8)
C180.52369 (13)0.4267 (3)0.18296 (13)0.0413 (8)
C120.45074 (14)0.4976 (3)0.22251 (15)0.0533 (9)
H12a0.3923870.4981060.1941320.064*
C140.55304 (15)0.5655 (3)0.34545 (14)0.0522 (9)
H14a0.5612950.6102010.4000520.0627*
C130.46523 (15)0.5645 (3)0.30108 (15)0.0555 (10)
H13a0.4166060.6106330.3264530.0666*
C150.62592 (14)0.5020 (3)0.30951 (13)0.0442 (8)
H15a0.6837590.5044970.3389180.053*
C100.6400 (2)0.1763 (4)0.05197 (16)0.0789 (12)
H10a0.6311770.1315330.106540.0946*
C110.56781 (17)0.2291 (3)0.01395 (15)0.0689 (11)
H11a0.5096710.2199060.0423730.0827*
C90.72833 (18)0.1879 (3)0.01060 (16)0.0685 (12)
H9a0.7772450.1528770.0386190.0822*
H3a0.9191910.2790020.4401530.138 (12)*
H1a0.7731390.4026660.2291660.105 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0634 (10)0.0734 (13)0.0442 (9)0.0001 (9)0.0122 (8)0.0094 (9)
O10.0315 (8)0.0749 (13)0.0545 (10)0.0027 (8)0.0009 (7)0.0096 (9)
C10.0315 (11)0.0413 (14)0.0394 (12)0.0004 (10)0.0046 (10)0.0033 (11)
O70.0556 (10)0.1066 (17)0.0520 (10)0.0111 (10)0.0040 (8)0.0199 (11)
C40.0326 (11)0.0468 (15)0.0457 (13)0.0043 (11)0.0016 (11)0.0111 (12)
C50.0325 (11)0.0414 (15)0.0398 (12)0.0028 (10)0.0059 (10)0.0035 (11)
O20.0445 (9)0.0836 (14)0.0637 (10)0.0069 (9)0.0161 (8)0.0161 (10)
C20.0493 (13)0.0426 (15)0.0377 (12)0.0029 (12)0.0073 (11)0.0033 (12)
C30.0449 (12)0.0468 (16)0.0337 (12)0.0128 (11)0.0024 (10)0.0056 (12)
N10.0646 (15)0.090 (2)0.0420 (13)0.0141 (14)0.0078 (12)0.0014 (13)
C70.0413 (13)0.0461 (16)0.0509 (14)0.0004 (12)0.0098 (11)0.0019 (13)
C60.0334 (11)0.0433 (14)0.0381 (12)0.0051 (10)0.0003 (10)0.0035 (11)
O60.0328 (8)0.1225 (17)0.0871 (12)0.0130 (10)0.0128 (8)0.0119 (12)
O40.1041 (16)0.197 (3)0.0807 (15)0.0108 (16)0.0151 (13)0.0758 (17)
N20.0369 (11)0.0590 (15)0.0567 (13)0.0011 (11)0.0116 (10)0.0046 (12)
O50.0575 (11)0.177 (2)0.0581 (11)0.0108 (14)0.0193 (9)0.0056 (13)
N30.0310 (9)0.0431 (12)0.0419 (10)0.0041 (9)0.0024 (8)0.0009 (10)
N40.0446 (11)0.0533 (14)0.0545 (12)0.0017 (10)0.0065 (9)0.0035 (11)
C170.0538 (14)0.0491 (17)0.0469 (14)0.0046 (13)0.0024 (12)0.0024 (13)
C190.0354 (12)0.0362 (14)0.0412 (13)0.0040 (11)0.0029 (10)0.0023 (11)
C80.0564 (15)0.0521 (18)0.0588 (16)0.0030 (13)0.0136 (13)0.0013 (13)
C160.0459 (13)0.0339 (14)0.0419 (13)0.0006 (11)0.0057 (11)0.0018 (11)
C180.0352 (11)0.0378 (15)0.0504 (13)0.0009 (11)0.0032 (10)0.0008 (12)
C120.0355 (13)0.0510 (17)0.0730 (17)0.0020 (12)0.0041 (12)0.0052 (14)
C140.0630 (15)0.0471 (17)0.0484 (14)0.0037 (14)0.0143 (13)0.0049 (13)
C130.0457 (14)0.0512 (18)0.0728 (18)0.0032 (13)0.0208 (13)0.0040 (15)
C150.0419 (13)0.0481 (16)0.0418 (13)0.0029 (12)0.0012 (11)0.0047 (12)
C100.107 (2)0.078 (2)0.0504 (16)0.009 (2)0.0051 (17)0.0198 (16)
C110.0775 (19)0.071 (2)0.0533 (17)0.0057 (16)0.0147 (14)0.0148 (15)
C90.089 (2)0.060 (2)0.0602 (18)0.0060 (17)0.0270 (15)0.0069 (16)
Geometric parameters (Å, º) top
O3—C21.329 (3)N4—C171.332 (3)
O3—H3a1.0592 (14)N4—C181.344 (3)
O1—C71.282 (3)C17—C161.428 (3)
O1—H1a1.1628 (13)C17—C111.421 (3)
C1—C21.410 (3)C19—C181.423 (3)
C1—C71.487 (3)C19—C151.407 (3)
C1—C61.373 (3)C8—H8a0.93
O7—N21.219 (2)C8—C161.413 (3)
C4—H4a0.93C8—C91.349 (3)
C4—C51.379 (3)C18—C121.412 (3)
C4—C31.371 (3)C12—H12a0.93
C5—C61.376 (3)C12—C131.347 (3)
C5—N21.459 (3)C14—H14a0.93
O2—C71.234 (3)C14—C131.410 (3)
C2—C31.404 (3)C14—C151.361 (3)
C3—N11.464 (3)C13—H13a0.93
N1—O41.194 (3)C15—H15a0.93
N1—O51.204 (3)C10—H10a0.93
C6—H6a0.93C10—C111.346 (4)
O6—N21.217 (2)C10—C91.400 (4)
N3—C191.346 (3)C11—H11a0.93
N3—C161.346 (3)C9—H9a0.93
C2—O3—H3a105.60 (13)C16—C17—C11117.8 (2)
C7—O1—H1a113.94 (15)N3—C19—C18119.68 (18)
C2—C1—C7119.58 (18)N3—C19—C15120.03 (17)
C2—C1—C6120.63 (17)C18—C19—C15120.28 (19)
C7—C1—C6119.79 (17)H8a—C8—C16120.23
H4a—C4—C5120.49H8a—C8—C9120.23
H4a—C4—C3120.49C16—C8—C9119.5 (2)
C5—C4—C3119.01 (18)N3—C16—C17119.52 (18)
C4—C5—C6121.58 (19)N3—C16—C8120.61 (17)
C4—C5—N2119.83 (17)C17—C16—C8119.86 (19)
C6—C5—N2118.58 (17)N4—C18—C19121.90 (19)
C7—O2—H3a102.24 (13)N4—C18—C12119.74 (18)
O3—C2—C1120.09 (17)C19—C18—C12118.35 (19)
O3—C2—C3122.05 (17)C18—C12—H12a119.82
C1—C2—C3117.84 (19)C18—C12—C13120.35 (19)
C4—C3—C2121.34 (18)H12a—C12—C13119.82
C4—C3—N1116.79 (18)H14a—C14—C13119.52
C2—C3—N1121.86 (19)H14a—C14—C15119.52
C3—N1—O4119.3 (2)C13—C14—C15121.0 (2)
C3—N1—O5118.0 (2)C12—C13—C14121.0 (2)
O4—N1—O5122.7 (2)C12—C13—H13a119.52
O1—C7—C1115.30 (19)C14—C13—H13a119.52
O1—C7—O2123.93 (18)C19—C15—C14119.05 (18)
C1—C7—O2120.76 (18)C19—C15—H15a120.48
C1—C6—C5119.59 (17)C14—C15—H15a120.48
C1—C6—H6a120.21H10a—C10—C11119.51
C5—C6—H6a120.2H10a—C10—C9119.51
O7—N2—C5118.45 (16)C11—C10—C9121.0 (2)
O7—N2—O6122.87 (19)C17—C11—C10120.6 (2)
C5—N2—O6118.66 (17)C17—C11—H11a119.71
C19—N3—C16119.31 (15)C10—C11—H11a119.71
C19—N3—H1a119.38 (14)C8—C9—C10121.3 (3)
C16—N3—H1a120.79 (14)C8—C9—H9a119.37
C17—N4—C18117.41 (17)C10—C9—H9a119.37
N4—C17—C16122.14 (19)O3—H3a—O2151.72 (10)
N4—C17—C11120.09 (19)O1—H1a—N3163.24 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13a···O4i0.932.493.334 (3)151
O3—H3a···O21.0592 (14)1.5297 (14)2.5132 (19)151.72 (10)
O1—H1a···N31.1628 (13)1.4160 (14)2.5515 (19)163.24 (10)
Symmetry code: (i) x+3/2, y+1/2, z+1.
2-Amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate (NUQVEB) top
Crystal data top
C6H9N2+·C7H3N2O7Z = 2
Mr = 336.27F(000) = 348
Triclinic, P1Dx = 1.569 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.8673 (7) ÅCell parameters from 5139 reflections
b = 8.0991 (9) Åθ = 2.7–32.4°
c = 15.2437 (17) ŵ = 0.13 mm1
α = 86.844 (3)°T = 100 K
β = 84.252 (3)°Block, yellow
γ = 81.209 (3)°0.29 × 0.14 × 0.08 mm
V = 711.69 (14) Å3
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer
4943 independent reflections
Radiation source: fine-focus sealed tube3677 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 32.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 88
Tmin = 0.963, Tmax = 0.990k = 1211
12709 measured reflectionsl = 2223
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F > 3σ(F)] = 0.042Hydrogen site location: difference Fourier map
wR(F) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 2.06Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
4943 reflections(Δ/σ)max = 0.009
222 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.32 e Å3
34 constraints
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Number of fixed parameters: 15

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.50355 (15)0.28624 (11)0.24318 (6)0.0153 (3)
N20.82331 (16)0.41649 (12)0.19964 (6)0.0182 (3)
C10.67739 (18)0.36376 (13)0.26429 (7)0.0152 (3)
C20.35124 (18)0.22197 (14)0.30471 (7)0.0165 (3)
H20.2333130.1677250.2857310.0198*
C30.36539 (18)0.23424 (14)0.39257 (7)0.0180 (3)
C40.54266 (19)0.31918 (15)0.41642 (7)0.0200 (3)
H40.5560830.3320790.4771690.024*
C50.69461 (19)0.38301 (14)0.35491 (7)0.0186 (3)
H50.8111360.4399590.3728330.0223*
C60.2014 (2)0.16274 (17)0.46143 (8)0.0262 (4)
H6a0.1180190.2524390.4980840.0394*
H6b0.0901440.1107430.4324580.0394*
H6c0.2890830.0784570.4986080.0394*
O10.17284 (13)0.61818 (10)0.14277 (5)0.0201 (2)
O20.10549 (15)0.60964 (11)0.31689 (5)0.0252 (3)
O30.28472 (15)0.76461 (12)0.38855 (5)0.0275 (3)
O40.93312 (14)0.99538 (11)0.26216 (6)0.0242 (3)
O50.99966 (15)1.02486 (11)0.11988 (6)0.0279 (3)
O60.55543 (14)0.76370 (11)0.07523 (5)0.0224 (3)
O70.26607 (14)0.63258 (10)0.01549 (5)0.0199 (2)
N30.25052 (15)0.70323 (12)0.31961 (6)0.0172 (3)
N40.89095 (16)0.97282 (12)0.18597 (6)0.0190 (3)
C70.33912 (17)0.70052 (13)0.15501 (7)0.0141 (3)
C80.38900 (17)0.74506 (13)0.23906 (7)0.0144 (3)
C90.56997 (17)0.83259 (13)0.24874 (7)0.0156 (3)
H90.6014390.8597040.3057240.0187*
C100.70326 (17)0.87968 (13)0.17493 (7)0.0154 (3)
C110.66121 (18)0.84357 (13)0.09021 (7)0.0157 (3)
H110.7536950.8791430.0400520.0188*
C120.48279 (17)0.75522 (13)0.08058 (7)0.0139 (3)
C130.43623 (18)0.71649 (13)0.01006 (7)0.0165 (3)
H1o70.207680.6154570.0419230.044 (6)*0.62 (3)
H1o10.1868130.6130810.0815690.044 (6)*0.38 (3)
H2a0.8094760.3979730.1434020.035 (4)*
H2b0.9285720.4698910.2116570.048 (5)*
H10.4811170.2761330.1864430.032 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0166 (4)0.0168 (5)0.0130 (4)0.0032 (3)0.0023 (3)0.0006 (3)
N20.0194 (4)0.0221 (5)0.0147 (4)0.0085 (4)0.0004 (3)0.0009 (4)
C10.0166 (5)0.0137 (5)0.0152 (5)0.0012 (4)0.0022 (4)0.0004 (4)
C20.0142 (5)0.0162 (5)0.0192 (5)0.0026 (4)0.0015 (4)0.0007 (4)
C30.0182 (5)0.0180 (5)0.0168 (5)0.0011 (4)0.0004 (4)0.0009 (4)
C40.0239 (5)0.0239 (6)0.0127 (5)0.0043 (5)0.0035 (4)0.0007 (4)
C50.0201 (5)0.0201 (6)0.0169 (5)0.0054 (4)0.0041 (4)0.0004 (4)
C60.0238 (6)0.0324 (7)0.0219 (6)0.0077 (5)0.0028 (4)0.0047 (5)
O10.0192 (4)0.0259 (4)0.0176 (4)0.0108 (3)0.0027 (3)0.0010 (3)
O20.0275 (4)0.0281 (5)0.0220 (4)0.0141 (4)0.0034 (3)0.0013 (3)
O30.0290 (5)0.0434 (6)0.0120 (4)0.0097 (4)0.0019 (3)0.0062 (4)
O40.0215 (4)0.0234 (4)0.0302 (5)0.0036 (3)0.0110 (3)0.0066 (4)
O50.0227 (4)0.0276 (5)0.0354 (5)0.0122 (4)0.0009 (3)0.0022 (4)
O60.0280 (4)0.0278 (5)0.0128 (4)0.0102 (4)0.0001 (3)0.0006 (3)
O70.0229 (4)0.0252 (4)0.0139 (4)0.0096 (3)0.0034 (3)0.0010 (3)
N30.0168 (4)0.0200 (5)0.0145 (4)0.0020 (4)0.0017 (3)0.0002 (4)
N40.0154 (4)0.0150 (5)0.0275 (5)0.0027 (4)0.0051 (4)0.0025 (4)
C70.0135 (4)0.0136 (5)0.0150 (5)0.0010 (4)0.0022 (4)0.0010 (4)
C80.0145 (5)0.0155 (5)0.0128 (5)0.0016 (4)0.0000 (4)0.0003 (4)
C90.0144 (5)0.0156 (5)0.0169 (5)0.0000 (4)0.0038 (4)0.0031 (4)
C100.0128 (4)0.0131 (5)0.0210 (5)0.0030 (4)0.0035 (4)0.0018 (4)
C110.0148 (5)0.0137 (5)0.0179 (5)0.0009 (4)0.0007 (4)0.0005 (4)
C120.0145 (4)0.0141 (5)0.0132 (5)0.0020 (4)0.0018 (4)0.0009 (4)
C130.0190 (5)0.0153 (5)0.0151 (5)0.0021 (4)0.0026 (4)0.0012 (4)
Geometric parameters (Å, º) top
N1—C11.3498 (15)O1—H1o10.9310 (8)
N1—C21.3674 (14)O2—N31.2280 (14)
N1—H10.8977 (9)O3—N31.2338 (13)
N2—C11.3353 (14)O4—N41.2402 (14)
N2—H2a0.8921 (9)O5—N41.2273 (13)
N2—H2b0.8456 (10)O6—C131.2340 (13)
C1—C51.4139 (15)O7—C131.3022 (15)
C2—H20.95O7—H1o70.9185 (8)
C2—C31.3602 (16)N3—C81.4564 (13)
C3—C41.4174 (17)N4—C101.4544 (15)
C3—C61.5049 (16)C7—C81.4197 (15)
C4—H40.95C7—C121.4357 (14)
C4—C51.3643 (16)C8—C91.3874 (16)
C5—H50.95C9—H90.95
C6—H6a0.98C9—C101.3750 (15)
C6—H6b0.98C10—C111.3934 (16)
C6—H6c0.98C11—H110.95
H6a—H6b1.6003C11—C121.3787 (16)
H6a—H6c1.6003C12—C131.4939 (15)
H6b—H6c1.6003H2a—H2b1.4990 (2)
O1—C71.2964 (14)
C1—N1—C2123.29 (9)O2—N3—O3122.52 (9)
C1—N1—H1120.41 (9)O2—N3—C8119.61 (9)
C2—N1—H1116.29 (10)O3—N3—C8117.87 (10)
C1—N2—H2a120.74 (11)O4—N4—O5123.30 (10)
C1—N2—H2b120.05 (10)O4—N4—C10118.02 (9)
H2a—N2—H2b119.20 (10)O5—N4—C10118.69 (10)
N1—C1—N2118.98 (10)O1—C7—C8124.03 (9)
N1—C1—C5117.27 (9)O1—C7—C12119.84 (10)
N2—C1—C5123.75 (11)C8—C7—C12116.12 (10)
N1—C2—H2119.38N3—C8—C7121.67 (10)
N1—C2—C3121.25 (11)N3—C8—C9116.48 (9)
H2—C2—C3119.38C7—C8—C9121.84 (9)
C2—C3—C4116.54 (10)C8—C9—H9120.37
C2—C3—C6122.15 (11)C8—C9—C10119.26 (10)
C4—C3—C6121.31 (10)H9—C9—C10120.37
C3—C4—H4118.95N4—C10—C9118.68 (10)
C3—C4—C5122.10 (10)N4—C10—C11119.25 (9)
H4—C4—C5118.95C9—C10—C11122.05 (10)
C1—C5—C4119.51 (11)C10—C11—H11120.64
C1—C5—H5120.24C10—C11—C12118.72 (9)
C4—C5—H5120.24H11—C11—C12120.64
C3—C6—H6a109.47C7—C12—C11121.98 (10)
C3—C6—H6b109.47C7—C12—C13119.00 (10)
C3—C6—H6c109.47C11—C12—C13119.02 (9)
H6a—C6—H6b109.47O6—C13—O7123.12 (10)
H6a—C6—H6c109.47O6—C13—C12120.31 (10)
H6b—C6—H6c109.47O7—C13—C12116.57 (9)
C7—O1—H1o798.33 (6)O1—H1o7—O7161.55 (6)
C7—O1—H1o1101.65 (8)O7—H1o7—H1o1166.67 (6)
C13—O7—H1o7104.71 (9)O1—H1o1—O7163.52 (6)
C13—O7—H1o199.43 (7)O1—H1o1—H1o7171.56 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O4i0.952.473.4107 (16)169
C4—H4···O3ii0.952.383.2397 (15)151
C5—H5···O2iii0.952.433.2361 (16)143
O7—H1o7···O10.9185 (8)1.5313 (8)2.4202 (12)161.55 (6)
O1—H1o1···O70.9310 (8)1.5130 (8)2.4202 (12)163.52 (6)
N2—H2a···O7iv0.8921 (9)2.0783 (9)2.9655 (14)172.84 (6)
N2—H2b···O1iii0.8456 (10)2.1644 (9)2.8526 (14)138.40 (6)
N2—H2b···O2iii0.8456 (10)2.4133 (10)3.1741 (14)150.02 (6)
N1—H1···O6iv0.8977 (9)1.7828 (9)2.6781 (13)174.83 (6)
Symmetry codes: (i) x1, y1, z; (ii) x+1, y+1, z+1; (iii) x+1, y, z; (iv) x+1, y+1, z.
3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium 3,5-dinitro-2-hydroxybenzoate N,N-dimethylformamide monosolvate (QIQJAD) top
Crystal data top
C9H8Cl2N5+·C7H3N2O7·C3H7NOZ = 2
Mr = 557.31F(000) = 572
Triclinic, P1Dx = 1.564 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.0227 (5) ÅCell parameters from 6413 reflections
b = 10.5507 (5) Åθ = 2.3–28.2°
c = 12.5359 (6) ŵ = 0.34 mm1
α = 81.858 (1)°T = 294 K
β = 71.888 (1)°Plate, colourless
γ = 70.009 (1)°0.16 × 0.14 × 0.08 mm
V = 1183.1 (1) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5507 independent reflections
Radiation source: fine-focus sealed tube4441 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.019
ω scansθmax = 28.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1213
Tmin = 0.93, Tmax = 0.97k = 1313
13936 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
R[F > 3σ(F)] = 0.056Secondary atom site location: difference Fourier map
wR(F) = 0.147Hydrogen site location: difference Fourier map
S = 3.41H atoms treated by a mixture of independent and constrained refinement
5507 reflectionsWeighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
340 parameters(Δ/σ)max = 0.020
0 restraintsΔρmax = 0.80 e Å3
48 constraintsΔρmin = 0.36 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Number of fixed parameters: 18

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.32107 (18)1.06764 (19)0.15844 (16)0.0464 (7)
C20.2718 (2)1.0232 (2)0.08378 (15)0.0485 (7)
C30.2713 (2)1.0903 (2)0.02046 (16)0.0529 (8)
C40.3231 (2)1.2001 (2)0.04951 (19)0.0621 (9)
H40.3231271.2451730.118860.0745*
C50.3741 (2)1.2420 (2)0.02358 (19)0.0632 (10)
H50.4101271.3148570.0019370.0758*
C60.3745 (2)1.1807 (2)0.12857 (17)0.0537 (8)
H60.408161.2119240.1777270.0645*
C70.32753 (18)0.99894 (19)0.26974 (15)0.0437 (7)
C80.35068 (19)0.8912 (2)0.47363 (15)0.0449 (7)
C90.19780 (18)0.99408 (18)0.36291 (15)0.0418 (7)
N10.45735 (16)0.95248 (17)0.28531 (13)0.0488 (6)
N20.46755 (16)0.89842 (17)0.38722 (13)0.0484 (6)
N30.37354 (18)0.8352 (2)0.56859 (14)0.0613 (8)
N40.21299 (15)0.93978 (16)0.46191 (12)0.0454 (6)
N50.06397 (16)1.04599 (17)0.35102 (13)0.0504 (7)
Cl10.21444 (7)0.88366 (6)0.11855 (5)0.0685 (3)
Cl20.20368 (7)1.04039 (8)0.11161 (5)0.0772 (3)
C100.7671 (2)0.7509 (2)0.50260 (17)0.0495 (8)
C110.92521 (19)0.68875 (18)0.50532 (16)0.0456 (8)
C121.0399 (2)0.68056 (19)0.40501 (17)0.0482 (8)
C131.1855 (2)0.6217 (2)0.4120 (2)0.0565 (9)
C141.2169 (3)0.5728 (2)0.5120 (2)0.0650 (11)
H141.314290.5359920.5150210.078*
C151.1014 (3)0.5795 (2)0.6070 (2)0.0608 (10)
C160.9560 (2)0.63637 (19)0.60559 (18)0.0537 (9)
H160.8795920.6394420.6713130.0645*
N61.3082 (2)0.6096 (2)0.3083 (2)0.0763 (10)
N71.1324 (3)0.5213 (2)0.7146 (3)0.0870 (14)
O10.74835 (14)0.79734 (16)0.40757 (12)0.0638 (7)
O20.66684 (16)0.75284 (17)0.58991 (13)0.0695 (7)
O31.01381 (16)0.72881 (16)0.30779 (13)0.0651 (7)
O41.3027 (2)0.5624 (2)0.22939 (18)0.0962 (10)
O51.4096 (2)0.6460 (3)0.3106 (2)0.1311 (14)
O61.2621 (3)0.4654 (3)0.7114 (2)0.1272 (14)
O71.0297 (3)0.5356 (3)0.7980 (2)0.1153 (15)
C170.8968 (2)0.2419 (2)0.13898 (19)0.0638 (10)
H170.9970490.2257530.102840.0765*
C180.6486 (3)0.3564 (4)0.1366 (3)0.1002 (16)
H18a0.6005660.3622370.0798270.1503*
H18b0.6120840.4416650.1714970.1503*
H18c0.6281540.2877660.1921780.1503*
C190.8613 (4)0.3905 (3)0.0204 (2)0.0959 (16)
H19a0.8126840.384630.073670.1439*
H19b0.8424040.4836990.0083940.1439*
H19c0.9658940.3473770.0489290.1439*
N80.8043 (2)0.32305 (17)0.08649 (14)0.0588 (8)
O80.86513 (17)0.18476 (18)0.23111 (12)0.0693 (7)
H3n0.4599920.8086420.5793830.067 (7)*
H4n0.3006840.8316490.626650.058 (6)*
H2n0.5604480.8674230.3928780.069 (7)*
H5n0.011251.0407690.4067490.056 (6)*
H6n0.0434491.0867030.29060.052 (6)*
H3o0.9113780.7564830.3307910.131 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0300 (8)0.0541 (11)0.0483 (10)0.0081 (8)0.0060 (7)0.0055 (8)
C20.0354 (9)0.0578 (11)0.0464 (10)0.0118 (8)0.0044 (8)0.0068 (8)
C30.0364 (9)0.0682 (13)0.0443 (10)0.0090 (9)0.0049 (8)0.0047 (9)
C40.0457 (11)0.0737 (15)0.0546 (12)0.0053 (10)0.0119 (9)0.0038 (11)
C50.0580 (13)0.0599 (13)0.0701 (14)0.0224 (11)0.0153 (11)0.0054 (11)
C60.0442 (10)0.0589 (12)0.0502 (11)0.0107 (9)0.0112 (9)0.0032 (9)
C70.0323 (9)0.0527 (11)0.0433 (10)0.0115 (8)0.0076 (7)0.0053 (8)
C80.0316 (8)0.0564 (11)0.0446 (10)0.0113 (8)0.0096 (7)0.0050 (8)
C90.0305 (8)0.0502 (10)0.0430 (9)0.0112 (7)0.0074 (7)0.0072 (8)
N10.0326 (8)0.0622 (10)0.0469 (9)0.0126 (7)0.0079 (6)0.0007 (7)
N20.0282 (7)0.0679 (10)0.0450 (9)0.0113 (7)0.0098 (6)0.0005 (7)
N30.0343 (8)0.0949 (14)0.0468 (9)0.0152 (9)0.0110 (7)0.0078 (9)
N40.0293 (7)0.0618 (10)0.0417 (8)0.0119 (7)0.0077 (6)0.0027 (7)
N50.0307 (7)0.0730 (11)0.0421 (9)0.0106 (7)0.0102 (7)0.0001 (8)
Cl10.0784 (4)0.0786 (4)0.0600 (3)0.0419 (3)0.0150 (3)0.0059 (3)
Cl20.0721 (4)0.1162 (5)0.0522 (3)0.0373 (4)0.0190 (3)0.0090 (3)
C100.0386 (10)0.0504 (11)0.0597 (12)0.0073 (8)0.0180 (9)0.0107 (9)
C110.0404 (10)0.0417 (10)0.0597 (12)0.0103 (8)0.0219 (9)0.0067 (8)
C120.0395 (10)0.0464 (10)0.0641 (12)0.0136 (8)0.0218 (9)0.0030 (9)
C130.0384 (10)0.0512 (11)0.0826 (15)0.0101 (8)0.0220 (10)0.0101 (10)
C140.0504 (12)0.0533 (12)0.1065 (19)0.0093 (10)0.0465 (13)0.0135 (12)
C150.0692 (15)0.0506 (12)0.0797 (15)0.0144 (10)0.0492 (13)0.0036 (10)
C160.0578 (12)0.0501 (11)0.0625 (13)0.0162 (9)0.0287 (10)0.0069 (9)
N60.0372 (10)0.0779 (14)0.1062 (18)0.0082 (9)0.0156 (10)0.0157 (12)
N70.113 (2)0.0759 (15)0.1066 (19)0.0325 (14)0.0800 (17)0.0073 (14)
O10.0374 (7)0.0841 (11)0.0645 (9)0.0093 (7)0.0222 (7)0.0067 (8)
O20.0428 (8)0.0946 (12)0.0601 (9)0.0074 (8)0.0121 (7)0.0108 (8)
O30.0427 (8)0.0802 (10)0.0653 (9)0.0151 (7)0.0148 (7)0.0074 (8)
O40.0575 (10)0.1277 (17)0.0882 (13)0.0110 (11)0.0135 (9)0.0195 (12)
O50.0520 (11)0.164 (2)0.181 (2)0.0480 (13)0.0026 (13)0.0623 (18)
O60.1283 (19)0.1273 (18)0.142 (2)0.0037 (15)0.1080 (17)0.0100 (15)
O70.142 (2)0.159 (2)0.0879 (15)0.0849 (19)0.0675 (16)0.0370 (15)
C170.0454 (11)0.0753 (15)0.0575 (13)0.0065 (10)0.0078 (10)0.0085 (11)
C180.0568 (15)0.129 (3)0.120 (2)0.0180 (16)0.0417 (16)0.009 (2)
C190.123 (3)0.0831 (19)0.0697 (17)0.0251 (18)0.0261 (16)0.0120 (14)
N80.0593 (11)0.0601 (11)0.0548 (10)0.0096 (9)0.0229 (9)0.0033 (8)
O80.0558 (9)0.0937 (12)0.0520 (9)0.0195 (8)0.0165 (7)0.0097 (8)
Geometric parameters (Å, º) top
C1—C21.382 (3)C13—C141.374 (4)
C1—C61.427 (3)C13—N61.471 (3)
C1—C71.488 (3)C14—H140.93
C2—C31.396 (3)C14—C151.369 (3)
C3—C41.385 (4)C15—C161.378 (3)
C4—H40.93C15—N71.479 (4)
C4—C51.362 (4)C16—H160.93
C5—H50.93N6—O41.192 (4)
C5—C61.382 (3)N6—O51.213 (4)
C6—H60.93N7—O61.221 (4)
C7—C91.464 (2)N7—O71.202 (4)
C7—N11.291 (2)O3—H3o0.9258 (14)
C8—N21.342 (2)C17—H170.93
C8—N31.303 (3)C17—N81.305 (3)
C8—N41.345 (2)C17—O81.226 (3)
C9—N41.322 (2)C18—H18a0.96
C9—N51.312 (2)C18—H18b0.96
N1—N21.343 (2)C18—H18c0.96
N2—H2n0.8973 (16)C18—N81.425 (3)
N3—H3n0.8624 (18)H18a—H18b1.5677
N3—H4n0.8630 (15)H18a—H18c1.5677
N5—H5n0.8658 (14)H18b—H18c1.5677
N5—H6n0.8630 (16)C19—H19a0.96
C10—C111.503 (3)C19—H19b0.96
C10—O11.267 (3)C19—H19c0.96
C10—O21.231 (2)C19—N81.470 (3)
C11—C121.405 (2)H19a—H19b1.5677
C11—C161.382 (3)H19a—H19c1.5677
C12—C131.402 (3)H19b—H19c1.5677
C12—O31.321 (3)
C2—C1—C6120.20 (18)C11—C12—O3122.09 (17)
C2—C1—C7122.86 (19)C13—C12—O3120.57 (17)
C6—C1—C7116.9 (2)C12—C13—C14122.17 (18)
C1—C2—C3120.2 (2)C12—C13—N6118.7 (2)
C2—C3—C4119.6 (2)C14—C13—N6119.10 (19)
C3—C4—H4120.02C13—C14—H14120.79
C3—C4—C5120.0 (2)C13—C14—C15118.4 (2)
H4—C4—C5120.02H14—C14—C15120.79
C4—C5—H5118.63C14—C15—C16122.1 (2)
C4—C5—C6122.7 (2)C14—C15—N7119.4 (2)
H5—C5—C6118.63C16—C15—N7118.5 (2)
C1—C6—C5117.3 (2)C11—C16—C15119.19 (18)
C1—C6—H6121.37C11—C16—H16120.41
C5—C6—H6121.36C15—C16—H16120.41
C1—C7—C9124.50 (16)C13—N6—O4118.2 (2)
C1—C7—N1115.60 (15)C13—N6—O5117.0 (3)
C9—C7—N1119.58 (16)O4—N6—O5124.8 (2)
N2—C8—N3118.61 (17)C15—N7—O6116.6 (2)
N2—C8—N4120.57 (17)C15—N7—O7118.1 (3)
N3—C8—N4120.81 (16)O6—N7—O7125.3 (3)
C7—C9—N4120.53 (16)C10—O1—H3o101.27 (12)
C7—C9—N5120.93 (16)C12—O3—H3o99.28 (14)
N4—C9—N5118.52 (15)H17—C17—N8116.69
C7—N1—N2117.85 (14)H17—C17—O8116.69
C8—N2—N1123.77 (16)N8—C17—O8126.6 (2)
C8—N2—H2n122.42 (17)H18a—C18—H18b109.47
N1—N2—H2n113.82 (14)H18a—C18—H18c109.47
C8—N3—H3n122.28 (17)H18a—C18—N8109.47
C8—N3—H4n121.07 (18)H18b—C18—H18c109.47
H3n—N3—H4n116.2 (2)H18b—C18—N8109.47
C8—N4—C9117.69 (14)H18c—C18—N8109.47
C9—N5—H5n119.55 (17)H19a—C19—H19b109.47
C9—N5—H6n124.81 (16)H19a—C19—H19c109.47
H5n—N5—H6n115.64 (18)H19a—C19—N8109.47
C11—C10—O1115.76 (15)H19b—C19—H19c109.47
C11—C10—O2119.27 (19)H19b—C19—N8109.47
O1—C10—O2124.96 (19)H19c—C19—N8109.47
C10—C11—C12119.51 (18)C17—N8—C18120.7 (2)
C10—C11—C16119.71 (16)C17—N8—C19119.5 (2)
C12—C11—C16120.74 (18)C18—N8—C19119.6 (2)
C11—C12—C13117.3 (2)O1—H3o—O3161.33 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19a···O4i0.962.473.401 (4)163
N3—H3n···O20.8624 (18)1.9939 (16)2.854 (2)174.78 (11)
N3—H4n···O8ii0.8630 (15)2.0586 (14)2.921 (2)176.91 (12)
N2—H2n···O10.8973 (16)1.8310 (15)2.728 (2)177.45 (12)
N5—H5n···N4iii0.8658 (14)2.1409 (13)2.9992 (19)171.06 (11)
N5—H6n···O8iv0.8630 (16)2.0412 (16)2.760 (2)140.22 (10)
O3—H3o···O10.9258 (14)1.5621 (12)2.4572 (18)161.33 (12)
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+1, z+1; (iii) x, y+2, z+1; (iv) x1, y+1, z.
Bis(1,10-phenanthroline-5,6-dione-κ2N,N')silver(I) 3,5-dinitrosalicylate (SAFGUD) top
Crystal data top
[Ag(C12H6N2O2)](C7H3N2O7)F(000) = 1512
Mr = 755.36Dx = 1.817 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5197 reflections
a = 11.757 (2) Åθ = 3.2–25.4°
b = 18.297 (4) ŵ = 0.81 mm1
c = 13.223 (3) ÅT = 174 K
β = 103.91 (3)°Prism, yellow
V = 2761.1 (11) Å30.3 × 0.24 × 0.2 mm
Z = 4
Data collection top
Oxford Diffraction Gemini R Ultra
diffractometer
5013 independent reflections
Radiation source: fine-focus sealed tube3100 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.052
ω scansθmax = 25.4°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1411
Tmin = 0.780, Tmax = 0.910k = 1722
12726 measured reflectionsl = 1513
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F > 3σ(F)] = 0.062H-atom parameters constrained
wR(F) = 0.118Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
S = 1.64(Δ/σ)max = 0.016
5013 reflectionsΔρmax = 0.76 e Å3
444 parametersΔρmin = 0.63 e Å3
0 restraintsExtinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
56 constraintsExtinction coefficient: 2400 (800)
Primary atom site location: structure-invariant direct methods
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Number of fixed parameters 3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.21070 (4)0.44031 (3)0.52479 (4)0.0538 (2)
C10.4796 (5)0.5138 (3)0.6221 (4)0.043 (2)
H10.4406960.5582090.606890.0511*
C20.5975 (6)0.5153 (3)0.6692 (4)0.046 (2)
H20.6370090.5594830.6848730.0553*
C30.6551 (5)0.4500 (3)0.6925 (4)0.046 (2)
H30.7343910.4491180.7257290.0547*
C40.5946 (5)0.3859 (3)0.6661 (4)0.035 (2)
C50.6523 (8)0.3141 (4)0.6884 (5)0.068 (3)
C60.5912 (10)0.2510 (4)0.6718 (6)0.093 (5)
C70.4628 (6)0.2534 (3)0.6228 (4)0.042 (2)
C80.3994 (7)0.1881 (3)0.6033 (4)0.052 (3)
H80.4350890.1431840.62240.0623*
C90.2837 (7)0.1928 (4)0.5555 (5)0.063 (3)
H90.2386650.1506160.5401610.0756*
C100.2345 (6)0.2592 (3)0.5304 (5)0.052 (3)
H100.1555820.261070.4961880.0629*
C110.4065 (5)0.3197 (3)0.5966 (4)0.032 (2)
C120.4742 (5)0.3885 (3)0.6197 (4)0.033 (2)
C130.0851 (5)0.4150 (3)0.2774 (5)0.054 (3)
H130.1091470.3670480.2931740.0649*
C140.0376 (5)0.4324 (4)0.1743 (5)0.060 (3)
H140.0291510.3970850.1223580.0717*
C150.0032 (5)0.5033 (3)0.1508 (5)0.051 (3)
H150.0303710.5167790.0822740.0617*
C160.0190 (5)0.5550 (3)0.2306 (4)0.040 (2)
C170.0145 (5)0.6317 (3)0.2063 (5)0.051 (3)
C180.0094 (5)0.6826 (3)0.2940 (5)0.053 (3)
C190.0474 (5)0.6578 (3)0.4023 (5)0.042 (2)
C200.0689 (5)0.7058 (3)0.4858 (5)0.052 (3)
H200.0480990.7547260.4750140.063*
C210.1204 (6)0.6817 (4)0.5833 (5)0.058 (3)
H210.1346260.7131230.640290.0692*
C220.1503 (5)0.6091 (4)0.5941 (5)0.054 (3)
H220.1863520.592540.6605530.0653*
C230.0818 (5)0.5847 (3)0.4195 (4)0.036 (2)
C240.0637 (4)0.5318 (3)0.3326 (4)0.032 (2)
C250.6150 (6)0.4142 (3)0.9276 (4)0.041 (2)
C260.5079 (6)0.4527 (3)0.8869 (4)0.040 (2)
C270.4074 (5)0.4101 (3)0.8426 (4)0.037 (2)
C280.4091 (5)0.3351 (3)0.8456 (4)0.041 (2)
H280.3419980.3080640.8176160.0498*
C290.5156 (6)0.3004 (3)0.8924 (4)0.041 (2)
C300.6177 (5)0.3387 (3)0.9323 (4)0.043 (2)
H300.6870510.3141230.9618040.0515*
C310.2956 (6)0.4467 (4)0.7881 (5)0.047 (3)
N10.4179 (4)0.4525 (2)0.5968 (3)0.0338 (17)
N20.2929 (4)0.3229 (2)0.5519 (3)0.0387 (18)
N30.0989 (4)0.4627 (2)0.3563 (3)0.0413 (18)
N40.1317 (4)0.5603 (2)0.5163 (3)0.0405 (18)
N50.7267 (6)0.4510 (4)0.9628 (4)0.059 (3)
N60.5168 (6)0.2209 (3)0.9002 (4)0.055 (3)
O10.7646 (5)0.3117 (3)0.7273 (4)0.092 (3)
O20.6406 (5)0.1892 (3)0.6987 (4)0.102 (3)
O30.0421 (4)0.6544 (2)0.1169 (3)0.069 (2)
O40.0501 (5)0.7444 (2)0.2776 (4)0.081 (2)
O50.8168 (5)0.4145 (3)0.9750 (4)0.090 (3)
O60.7298 (5)0.5169 (3)0.9762 (4)0.084 (2)
O70.5025 (4)0.5233 (2)0.8850 (3)0.0617 (19)
O80.2936 (4)0.5168 (3)0.7945 (3)0.066 (2)
O90.2137 (4)0.4111 (3)0.7370 (3)0.064 (2)
O100.4286 (5)0.1877 (2)0.8580 (4)0.070 (2)
O110.6096 (5)0.1916 (2)0.9512 (4)0.068 (2)
H70.3888840.5317470.835910.019 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0474 (4)0.0492 (3)0.0603 (3)0.0150 (3)0.0038 (2)0.0149 (3)
C10.054 (5)0.035 (4)0.041 (3)0.006 (3)0.014 (3)0.001 (3)
C20.052 (5)0.041 (4)0.048 (4)0.010 (3)0.018 (3)0.001 (3)
C30.031 (4)0.063 (4)0.043 (3)0.004 (3)0.008 (3)0.008 (3)
C40.036 (4)0.034 (3)0.035 (3)0.015 (3)0.013 (3)0.004 (3)
C50.085 (7)0.078 (6)0.048 (4)0.014 (5)0.031 (4)0.006 (4)
C60.201 (12)0.037 (5)0.065 (5)0.012 (6)0.081 (7)0.001 (4)
C70.033 (4)0.059 (5)0.035 (3)0.007 (3)0.008 (3)0.001 (3)
C80.088 (6)0.023 (3)0.051 (4)0.010 (4)0.029 (4)0.005 (3)
C90.074 (6)0.053 (5)0.067 (5)0.009 (4)0.025 (4)0.008 (4)
C100.039 (4)0.054 (4)0.064 (4)0.003 (4)0.012 (3)0.014 (4)
C110.043 (4)0.026 (3)0.029 (3)0.006 (3)0.010 (3)0.002 (2)
C120.043 (4)0.031 (3)0.028 (3)0.004 (3)0.014 (3)0.002 (2)
C130.052 (5)0.034 (4)0.071 (5)0.002 (3)0.005 (4)0.001 (3)
C140.055 (5)0.055 (5)0.064 (4)0.000 (4)0.003 (4)0.024 (4)
C150.046 (4)0.057 (4)0.045 (4)0.004 (3)0.000 (3)0.002 (3)
C160.029 (3)0.038 (3)0.051 (4)0.000 (3)0.004 (3)0.005 (3)
C170.039 (4)0.054 (4)0.055 (4)0.002 (3)0.001 (3)0.021 (4)
C180.036 (4)0.042 (4)0.077 (5)0.003 (3)0.004 (3)0.005 (4)
C190.035 (4)0.032 (3)0.057 (4)0.003 (3)0.007 (3)0.002 (3)
C200.046 (4)0.031 (3)0.079 (5)0.000 (3)0.012 (4)0.010 (4)
C210.049 (5)0.055 (5)0.067 (5)0.002 (4)0.010 (4)0.013 (4)
C220.046 (4)0.070 (5)0.042 (4)0.003 (4)0.001 (3)0.006 (4)
C230.027 (3)0.034 (3)0.046 (3)0.002 (3)0.006 (3)0.000 (3)
C240.019 (3)0.031 (3)0.046 (3)0.001 (2)0.007 (2)0.004 (3)
C250.058 (5)0.037 (4)0.028 (3)0.010 (3)0.010 (3)0.004 (3)
C260.062 (5)0.032 (3)0.030 (3)0.001 (3)0.018 (3)0.002 (3)
C270.039 (4)0.038 (4)0.035 (3)0.002 (3)0.012 (3)0.006 (3)
C280.057 (5)0.041 (4)0.030 (3)0.007 (3)0.018 (3)0.002 (3)
C290.068 (5)0.029 (3)0.032 (3)0.004 (3)0.024 (3)0.005 (3)
C300.047 (4)0.047 (4)0.036 (3)0.005 (3)0.014 (3)0.002 (3)
C310.057 (5)0.041 (4)0.048 (4)0.011 (4)0.023 (3)0.008 (3)
N10.036 (3)0.031 (3)0.033 (2)0.005 (2)0.008 (2)0.001 (2)
N20.033 (3)0.037 (3)0.044 (3)0.001 (2)0.006 (2)0.002 (2)
N30.040 (3)0.029 (3)0.051 (3)0.001 (2)0.004 (2)0.003 (2)
N40.035 (3)0.043 (3)0.041 (3)0.003 (2)0.004 (2)0.006 (2)
N50.057 (4)0.072 (5)0.044 (3)0.015 (4)0.003 (3)0.009 (3)
N60.090 (5)0.039 (4)0.044 (3)0.004 (3)0.033 (3)0.004 (3)
O10.083 (4)0.104 (4)0.088 (4)0.034 (4)0.022 (3)0.021 (3)
O20.095 (5)0.085 (4)0.115 (5)0.014 (4)0.002 (4)0.007 (4)
O30.066 (3)0.071 (3)0.065 (3)0.002 (3)0.004 (3)0.026 (3)
O40.101 (4)0.040 (3)0.095 (4)0.019 (3)0.007 (3)0.017 (3)
O50.052 (4)0.100 (4)0.111 (4)0.002 (3)0.006 (3)0.031 (3)
O60.091 (4)0.051 (3)0.090 (4)0.024 (3)0.015 (3)0.003 (3)
O70.088 (4)0.042 (3)0.057 (3)0.005 (2)0.021 (3)0.002 (2)
O80.069 (4)0.060 (3)0.072 (3)0.017 (3)0.022 (3)0.009 (2)
O90.042 (3)0.084 (4)0.066 (3)0.006 (3)0.012 (2)0.002 (3)
O100.107 (5)0.039 (3)0.067 (3)0.016 (3)0.025 (3)0.001 (2)
O110.089 (4)0.042 (3)0.081 (3)0.016 (3)0.036 (3)0.022 (2)
Geometric parameters (Å, º) top
Ag1—N12.404 (4)C16—C241.392 (7)
Ag1—N22.348 (5)C17—C181.476 (9)
Ag1—N32.335 (4)C17—O31.220 (8)
Ag1—N42.376 (5)C18—C191.498 (8)
C1—H10.93C18—O41.227 (8)
C1—C21.376 (8)C19—C201.386 (8)
C1—N11.334 (7)C19—C231.400 (8)
C2—H20.93C20—H200.93
C2—C31.373 (8)C20—C211.359 (9)
C3—H30.93C21—H210.93
C3—C41.372 (8)C21—C221.373 (9)
C4—C51.475 (10)C22—H220.93
C4—C121.402 (8)C22—N41.341 (8)
C5—C61.349 (12)C23—C241.478 (7)
C5—O11.298 (10)C23—N41.349 (7)
C6—C71.493 (13)C24—N31.344 (7)
C6—O21.283 (10)C25—C261.430 (9)
C7—C81.399 (9)C25—C301.384 (8)
C7—C111.385 (8)C25—N51.450 (9)
C8—H80.93C26—C271.418 (8)
C8—C91.357 (10)C26—O71.293 (7)
C9—H90.93C27—C281.373 (8)
C9—C101.353 (9)C27—C311.496 (8)
C10—H100.93C28—H280.93
C10—N21.347 (8)C28—C291.407 (8)
C11—C121.481 (7)C29—C301.380 (8)
C11—N21.326 (7)C29—N61.458 (8)
C12—N11.344 (7)C30—H300.93
C13—H130.93C31—O81.286 (8)
C13—C141.381 (9)C31—O91.223 (8)
C13—N31.339 (8)N5—O51.230 (9)
C14—H140.93N5—O61.218 (8)
C14—C151.373 (9)N6—O101.216 (8)
C15—H150.93N6—O111.257 (8)
C15—C161.396 (8)O7—H71.346 (4)
C16—C171.473 (8)O8—H71.155 (4)
H1—C1—C2118.04C19—C18—O4120.9 (6)
H1—C1—N1118.04C18—C19—C20121.6 (5)
C2—C1—N1123.9 (5)C18—C19—C23119.3 (5)
C1—C2—H2120.88C20—C19—C23119.1 (5)
C1—C2—C3118.2 (5)C19—C20—H20119.84
H2—C2—C3120.88C19—C20—C21120.3 (6)
C2—C3—H3120.34H20—C20—C21119.84
C2—C3—C4119.3 (5)C20—C21—H21121.42
H3—C3—C4120.34C20—C21—C22117.2 (6)
C3—C4—C5121.7 (6)H21—C21—C22121.42
C3—C4—C12119.3 (5)C21—C22—H22117.46
C5—C4—C12119.0 (5)C21—C22—N4125.1 (5)
C4—C5—C6121.9 (8)H22—C22—N4117.46
C4—C5—O1118.9 (7)C19—C23—C24121.2 (5)
C6—C5—O1119.2 (8)C19—C23—N4120.8 (5)
C5—C6—C7119.3 (7)C24—C23—N4118.0 (5)
C5—C6—O2121.4 (9)C16—C24—C23120.2 (5)
C7—C6—O2119.3 (7)C16—C24—N3122.5 (5)
C6—C7—C8119.6 (6)C23—C24—N3117.2 (4)
C6—C7—C11120.4 (6)C26—C25—C30121.2 (5)
C8—C7—C11120.0 (6)C26—C25—N5122.7 (5)
C7—C8—H8121.23C30—C25—N5116.1 (6)
C7—C8—C9117.5 (6)C25—C26—C27117.1 (5)
H8—C8—C9121.23C25—C26—O7122.2 (5)
C8—C9—H9120.26C27—C26—O7120.5 (5)
C8—C9—C10119.5 (6)C26—C27—C28122.1 (5)
H9—C9—C10120.26C26—C27—C31120.1 (5)
C9—C10—H10118.01C28—C27—C31117.8 (5)
C9—C10—N2124.0 (6)C27—C28—H28121
H10—C10—N2118.01C27—C28—C29118.0 (5)
C7—C11—C12119.5 (5)H28—C28—C29121
C7—C11—N2121.3 (5)C28—C29—C30122.6 (5)
C12—C11—N2119.2 (5)C28—C29—N6118.3 (5)
C4—C12—C11119.8 (5)C30—C29—N6119.1 (5)
C4—C12—N1121.2 (5)C25—C30—C29118.7 (5)
C11—C12—N1118.9 (5)C25—C30—H30120.65
H13—C13—C14117.83C29—C30—H30120.65
H13—C13—N3117.83C27—C31—O8116.2 (5)
C14—C13—N3124.3 (5)C27—C31—O9120.8 (6)
C13—C14—H14121.04O8—C31—O9122.9 (6)
C13—C14—C15117.9 (6)C1—N1—C12117.9 (4)
H14—C14—C15121.04C10—N2—C11117.6 (5)
C14—C15—H15120.29C13—N3—C24117.3 (5)
C14—C15—C16119.4 (5)C22—N4—C23117.5 (5)
H15—C15—C16120.29C25—N5—O5118.4 (6)
C15—C16—C17120.1 (5)C25—N5—O6120.0 (6)
C15—C16—C24118.5 (5)O5—N5—O6121.6 (6)
C17—C16—C24121.4 (5)C29—N6—O10118.3 (5)
C16—C17—C18118.1 (5)C29—N6—O11117.2 (5)
C16—C17—O3122.0 (6)O10—N6—O11124.5 (5)
C18—C17—O3119.9 (6)C26—O7—H799.4 (4)
C17—C18—C19119.0 (5)C31—O8—H7103.7 (4)
C17—C18—O4120.1 (6)O7—H7—O8159.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O10i0.932.493.180 (7)131
C8—H8···O7ii0.932.323.220 (7)162
C9—H9···O6ii0.932.493.243 (9)138
C13—H13···O4iii0.932.473.209 (7)137
C22—H22···O80.932.363.251 (7)160
O7—H7···C311.346 (4)1.922 (7)2.833 (8)119.1 (3)
O7—H7···O81.346 (4)1.155 (4)2.462 (6)159.6 (3)
O8—H7···C261.155 (4)2.013 (6)2.781 (7)120.3 (3)
O8—H7···O71.155 (4)1.346 (4)2.462 (6)159.6 (3)
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+1, y1/2, z+3/2; (iii) x, y1/2, z+1/2.
3,5-Dimethylpyrazolium 3,5-dinitrosalicylate (SEDKET) top
Crystal data top
C5H9N2+·C7H3N2O7F(000) = 336
Mr = 324.26Dx = 1.547 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 8.1183 (7) ÅCell parameters from 1025 reflections
b = 6.0636 (5) Åθ = 2.5–22.6°
c = 14.1453 (11) ŵ = 0.13 mm1
β = 91.904 (1)°T = 293 K
V = 695.93 (10) Å3Block, colorless
Z = 20.40 × 0.27 × 0.11 mm
Data collection top
Bruker SMART CCD
diffractometer
2301 independent reflections
Radiation source: fine-focus sealed tube1444 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.040
ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 99
Tmin = 0.959, Tmax = 0.986k = 77
3523 measured reflectionsl = 1612
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F > 3σ(F)] = 0.041Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
wR(F) = 0.088(Δ/σ)max = 0.033
S = 1.16Δρmax = 0.11 e Å3
2301 reflectionsΔρmin = 0.10 e Å3
212 parametersExtinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
0 restraintsExtinction coefficient: 3100 (400)
37 constraintsAbsolute structure: 955 of Friedel pairs used in the refinement
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.5
Secondary atom site location: difference Fourier map
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Number of fixed parameters 10.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.2262 (4)0.7164 (5)0.2338 (2)0.0464 (11)
N20.2203 (3)0.6196 (5)0.3198 (2)0.0478 (11)
C60.3519 (4)0.7226 (6)0.5525 (2)0.0412 (12)
N30.2179 (3)1.3158 (5)0.7705 (2)0.0509 (12)
N40.5552 (4)0.7120 (5)0.8913 (2)0.0501 (12)
O10.5417 (3)0.5285 (4)0.70239 (16)0.0462 (9)
O20.4266 (3)0.5357 (4)0.53811 (15)0.0582 (10)
O30.2657 (3)0.8100 (4)0.49006 (14)0.0507 (8)
O40.1415 (3)1.4013 (4)0.70419 (18)0.0652 (10)
O50.2270 (3)1.3968 (4)0.85025 (18)0.0709 (11)
O60.5263 (4)0.7839 (5)0.96960 (17)0.0853 (12)
O70.6549 (4)0.5664 (5)0.87980 (17)0.0719 (12)
C10.1300 (5)0.6431 (8)0.0685 (2)0.0762 (19)
H1a0.1321190.8002980.0607330.1144*
H1b0.0275250.5860150.0430680.1144*
H1c0.2196990.5783960.0357440.1144*
C20.1466 (4)0.5878 (6)0.1713 (2)0.0469 (13)
C30.0892 (4)0.4058 (7)0.2187 (3)0.0553 (14)
H30.0296510.2885880.1924460.0663*
C40.1373 (4)0.4313 (6)0.3133 (2)0.0481 (13)
C50.1093 (5)0.2896 (7)0.3966 (3)0.0669 (16)
H5a0.0251420.1832510.3809140.1003*
H5b0.209640.2145510.4144770.1003*
H5c0.0748820.3793020.4482380.1003*
C120.4691 (4)0.7102 (6)0.7196 (2)0.0372 (12)
C70.3736 (3)0.8233 (6)0.6477 (2)0.0348 (11)
C80.2972 (4)1.0181 (6)0.6641 (2)0.0380 (12)
H80.2398051.0895160.6150130.0456*
C90.3044 (4)1.1108 (6)0.7534 (2)0.0381 (11)
C100.3902 (4)1.0091 (6)0.8274 (2)0.0403 (12)
H100.3937511.0711210.8876030.0483*
C110.4704 (4)0.8133 (6)0.8100 (2)0.0380 (11)
H2a0.507 (5)0.485 (9)0.620 (3)0.145 (19)*
H10.289 (6)0.878 (9)0.225 (3)0.130 (19)*
H20.258 (4)0.707 (6)0.373 (2)0.063 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0502 (18)0.049 (2)0.0399 (18)0.0006 (15)0.0027 (14)0.0034 (15)
N20.0497 (19)0.051 (2)0.0422 (18)0.0046 (17)0.0047 (14)0.0066 (17)
C60.0393 (19)0.047 (2)0.037 (2)0.0016 (18)0.0053 (16)0.0027 (18)
N30.0500 (19)0.043 (2)0.060 (2)0.0003 (17)0.0048 (16)0.0031 (18)
N40.065 (2)0.046 (2)0.0387 (19)0.0015 (17)0.0037 (16)0.0042 (16)
O10.0564 (15)0.0414 (15)0.0407 (14)0.0091 (13)0.0027 (11)0.0072 (12)
O20.0704 (17)0.0626 (18)0.0414 (14)0.0205 (15)0.0036 (12)0.0156 (14)
O30.0581 (14)0.0600 (17)0.0333 (13)0.0050 (14)0.0083 (11)0.0013 (12)
O40.0703 (17)0.0521 (17)0.0721 (18)0.0185 (15)0.0141 (14)0.0031 (15)
O50.092 (2)0.0593 (19)0.0617 (17)0.0072 (16)0.0048 (14)0.0187 (15)
O60.148 (3)0.075 (2)0.0326 (16)0.035 (2)0.0069 (15)0.0032 (15)
O70.092 (2)0.072 (2)0.0510 (16)0.0308 (19)0.0083 (14)0.0090 (16)
C10.086 (3)0.096 (4)0.047 (2)0.014 (3)0.009 (2)0.007 (2)
C20.043 (2)0.054 (3)0.0434 (19)0.005 (2)0.0046 (17)0.009 (2)
C30.049 (2)0.057 (3)0.060 (2)0.004 (2)0.0075 (18)0.022 (2)
C40.039 (2)0.044 (2)0.062 (2)0.0027 (19)0.0037 (17)0.003 (2)
C50.066 (3)0.060 (3)0.074 (3)0.000 (2)0.002 (2)0.012 (2)
C120.0351 (19)0.041 (2)0.036 (2)0.0079 (18)0.0025 (15)0.0010 (17)
C70.0342 (17)0.039 (2)0.0316 (17)0.0052 (17)0.0004 (13)0.0031 (16)
C80.041 (2)0.038 (2)0.0349 (19)0.0032 (18)0.0036 (15)0.0039 (17)
C90.041 (2)0.032 (2)0.0416 (19)0.0045 (17)0.0020 (15)0.0015 (17)
C100.049 (2)0.039 (2)0.0325 (19)0.0038 (18)0.0020 (16)0.0017 (17)
C110.0419 (19)0.041 (2)0.0312 (17)0.0038 (19)0.0025 (14)0.0049 (17)
Geometric parameters (Å, º) top
N1—N21.353 (4)H1a—H1b1.5677
N1—C21.330 (5)H1a—H1c1.5677
N1—H11.11 (5)H1b—H1c1.5677
N2—C41.327 (5)C2—C31.380 (5)
N2—H20.96 (3)C3—H30.93
C6—O21.304 (4)C3—C41.389 (5)
C6—O31.229 (4)C4—C51.482 (5)
C6—C71.484 (4)C5—H5a0.96
N3—O41.223 (4)C5—H5b0.96
N3—O51.231 (4)C5—H5c0.96
N3—C91.452 (5)H5a—H5b1.5677
N4—O61.220 (4)H5a—H5c1.5677
N4—O71.213 (4)H5b—H5c1.5677
N4—C111.457 (4)C12—C71.433 (4)
O1—C121.277 (4)C12—C111.422 (4)
O1—H2a1.22 (5)C7—C81.358 (5)
O2—H2a1.34 (5)C8—H80.93
C1—H1a0.96C8—C91.382 (4)
C1—H1b0.96C9—C101.384 (4)
C1—H1c0.96C10—H100.93
C1—C21.494 (5)C10—C111.380 (5)
N2—N1—C2108.2 (3)N2—C4—C3106.8 (3)
N2—N1—H1121 (2)N2—C4—C5122.3 (3)
C2—N1—H1131 (2)C3—C4—C5130.9 (3)
N1—N2—C4110.1 (3)C4—C5—H5a109.47
N1—N2—H2117 (2)C4—C5—H5b109.47
C4—N2—H2132 (2)C4—C5—H5c109.47
O2—C6—O3121.3 (3)H5a—C5—H5b109.47
O2—C6—C7117.2 (3)H5a—C5—H5c109.47
O3—C6—C7121.5 (3)H5b—C5—H5c109.47
O4—N3—O5123.2 (3)O1—C12—C7121.3 (3)
O4—N3—C9118.1 (3)O1—C12—C11124.1 (3)
O5—N3—C9118.7 (3)C7—C12—C11114.5 (3)
O6—N4—O7122.1 (3)C6—C7—C12119.5 (3)
O6—N4—C11117.8 (3)C6—C7—C8118.1 (3)
O7—N4—C11120.1 (3)C12—C7—C8122.3 (3)
C12—O1—H2a106 (2)C7—C8—H8119.87
C6—O2—H2a106 (2)C7—C8—C9120.3 (3)
H1a—C1—H1b109.47H8—C8—C9119.87
H1a—C1—H1c109.47N3—C9—C8119.6 (3)
H1a—C1—C2109.47N3—C9—C10119.3 (3)
H1b—C1—H1c109.47C8—C9—C10121.0 (3)
H1b—C1—C2109.47C9—C10—H10120.77
H1c—C1—C2109.47C9—C10—C11118.5 (3)
N1—C2—C1122.8 (3)H10—C10—C11120.77
N1—C2—C3108.1 (3)N4—C11—C12120.9 (3)
C1—C2—C3129.1 (3)N4—C11—C10115.7 (3)
C2—C3—H3126.58C12—C11—C10123.3 (3)
C2—C3—C4106.8 (3)O1—H2a—O2149 (5)
H3—C3—C4126.58
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1a···O7i0.962.493.176 (5)128
C5—H5a···O4ii0.962.473.395 (5)162
C10—H10···O6iii0.932.473.369 (4)164
O1—H2a···O21.22 (5)1.34 (5)2.476 (3)149 (5)
O2—H2a···O11.34 (5)1.22 (5)2.476 (3)149 (5)
N1—H1···O1i1.11 (5)1.92 (5)2.799 (4)133 (3)
N1—H1···O7i1.11 (5)1.94 (5)2.850 (4)137 (3)
N2—H2···O30.96 (3)1.77 (3)2.685 (4)158 (3)
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x, y3/2, z+1; (iii) x+1, y+1/2, z+2.
3-(1H-Imidazol-1-yl)propanaminium 2-carboxy-4,6-dinitrophenolate (TIYZIM) top
Crystal data top
C6H12N3+·C7H3N2O7Z = 2
Mr = 353.30F(000) = 368
Triclinic, P1Dx = 1.525 Mg m3
a = 7.0109 (4) ÅCu Kα radiation, λ = 1.54184 Å
b = 10.6617 (8) ÅCell parameters from 2218 reflections
c = 10.7454 (7) Åθ = 4.2–72.3°
α = 93.075 (6)°µ = 1.09 mm1
β = 95.863 (5)°T = 173 K
γ = 104.944 (6)°Irregular, yellow
V = 769.30 (9) Å30.22 × 0.14 × 0.12 mm
Data collection top
Agilent Xcalibur (Eos, Gemini)
diffractometer
2953 independent reflections
Graphite monochromator2426 reflections with I > 3σ(I)
Detector resolution: 16.0416 pixels mm-1Rint = 0.026
ω scansθmax = 72.5°, θmin = 4.2°
Absorption correction: multi-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
h = 85
Tmin = 0.925, Tmax = 1.000k = 1213
4664 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F > 3σ(F)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F) = 0.100Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
S = 1.64(Δ/σ)max = 0.013
2953 reflectionsΔρmax = 0.21 e Å3
229 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
46 constraintsExtinction coefficient: 740 (130)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Number of fixed parameters: 12

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1b0.19161 (17)0.67539 (12)0.52684 (11)0.0294 (4)
O2b0.38292 (17)0.47166 (12)0.40838 (12)0.0313 (4)
O3b0.25511 (17)0.37712 (12)0.26158 (12)0.0312 (4)
O4b0.41258 (19)0.58639 (13)0.16853 (13)0.0365 (5)
O5b0.59776 (18)0.75622 (13)0.28239 (14)0.0382 (5)
O6b0.3446 (2)0.93719 (14)0.62658 (15)0.0474 (5)
O7b0.02822 (19)0.91655 (13)0.61477 (13)0.0410 (5)
N1b0.1720 (2)0.88469 (14)0.58118 (14)0.0301 (5)
N2b0.4396 (2)0.67347 (14)0.25363 (14)0.0281 (5)
C1b0.0455 (2)0.68023 (16)0.46268 (15)0.0225 (5)
C2b0.0572 (2)0.57873 (15)0.36597 (15)0.0217 (5)
C3b0.0987 (2)0.57933 (16)0.29810 (15)0.0228 (5)
H3b0.0861720.5125620.2332190.0273*
C4b0.2738 (2)0.67709 (16)0.32422 (15)0.0238 (5)
C5b0.2967 (2)0.77664 (16)0.41630 (15)0.0244 (5)
H5b0.4184940.8426180.4336770.0292*
C6b0.1392 (2)0.77850 (16)0.48267 (15)0.0244 (5)
C7b0.2405 (2)0.46767 (16)0.33986 (15)0.0245 (5)
N1a0.2235 (2)0.05127 (14)0.17301 (14)0.0305 (5)
N2a0.0146 (2)0.22579 (13)0.06967 (13)0.0239 (4)
N3a0.3467 (2)0.20531 (13)0.28160 (13)0.0254 (4)
C1a0.0395 (2)0.12591 (16)0.15749 (16)0.0272 (6)
H1a0.063240.1110940.2027720.0327*
C2a0.3211 (3)0.10665 (17)0.08987 (17)0.0314 (6)
H2a0.4574430.074320.0791160.0377*
C3a0.1954 (3)0.21356 (17)0.02572 (17)0.0294 (6)
H3a0.2258450.2690840.037060.0353*
C4a0.1719 (2)0.32466 (17)0.02832 (15)0.0268 (5)
H4aa0.2420140.3513320.1019650.0322*
H4ab0.1427080.4037980.0084810.0322*
C5a0.3076 (2)0.27759 (16)0.06668 (16)0.0271 (5)
H5aa0.3244870.1931340.0336640.0326*
H5ab0.4406670.3404340.0791140.0326*
C6a0.2253 (2)0.26206 (16)0.19085 (15)0.0279 (6)
H6aa0.2182270.3478910.2270270.0335*
H6ab0.087120.2060210.177260.0335*
H2b0.3391340.5541440.461480.075 (9)*
H3aa0.3297810.1195320.2607010.045 (4)*
H3ab0.4758270.2487040.2845540.045 (4)*
H3ac0.3131450.212090.3591890.045 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1b0.0268 (6)0.0307 (7)0.0277 (6)0.0010 (5)0.0098 (5)0.0050 (5)
O2b0.0247 (6)0.0313 (7)0.0327 (7)0.0024 (5)0.0088 (5)0.0060 (5)
O3b0.0283 (6)0.0285 (7)0.0317 (7)0.0002 (5)0.0047 (5)0.0082 (5)
O4b0.0371 (7)0.0325 (7)0.0413 (8)0.0085 (6)0.0167 (6)0.0042 (6)
O5b0.0231 (6)0.0380 (8)0.0506 (9)0.0010 (6)0.0111 (6)0.0014 (6)
O6b0.0352 (7)0.0408 (8)0.0552 (10)0.0009 (6)0.0052 (7)0.0197 (7)
O7b0.0398 (7)0.0333 (7)0.0470 (8)0.0034 (6)0.0162 (6)0.0121 (6)
N1b0.0326 (8)0.0241 (8)0.0301 (8)0.0012 (6)0.0060 (6)0.0023 (6)
N2b0.0260 (7)0.0259 (7)0.0343 (8)0.0074 (6)0.0092 (6)0.0063 (6)
C1b0.0234 (8)0.0236 (8)0.0201 (8)0.0054 (6)0.0034 (6)0.0027 (6)
C2b0.0218 (8)0.0215 (8)0.0207 (8)0.0036 (6)0.0019 (6)0.0029 (6)
C3b0.0265 (8)0.0220 (8)0.0208 (8)0.0077 (7)0.0043 (6)0.0017 (6)
C4b0.0220 (8)0.0254 (8)0.0260 (8)0.0080 (7)0.0064 (7)0.0057 (7)
C5b0.0220 (8)0.0220 (8)0.0269 (8)0.0015 (6)0.0023 (7)0.0050 (7)
C6b0.0276 (8)0.0210 (8)0.0230 (8)0.0045 (7)0.0018 (7)0.0001 (6)
C7b0.0247 (8)0.0261 (8)0.0216 (8)0.0051 (7)0.0021 (6)0.0007 (6)
N1a0.0292 (8)0.0252 (8)0.0349 (8)0.0050 (6)0.0011 (6)0.0007 (6)
N2a0.0247 (7)0.0234 (7)0.0229 (7)0.0054 (6)0.0034 (5)0.0002 (6)
N3a0.0268 (7)0.0229 (7)0.0245 (7)0.0041 (6)0.0021 (6)0.0026 (6)
C1a0.0286 (9)0.0260 (9)0.0278 (9)0.0087 (7)0.0051 (7)0.0018 (7)
C2a0.0269 (9)0.0316 (10)0.0352 (10)0.0047 (7)0.0073 (7)0.0060 (8)
C3a0.0301 (9)0.0311 (9)0.0289 (9)0.0095 (7)0.0092 (7)0.0016 (7)
C4a0.0277 (8)0.0248 (8)0.0248 (8)0.0009 (7)0.0052 (7)0.0000 (7)
C5a0.0237 (8)0.0295 (9)0.0260 (9)0.0030 (7)0.0055 (7)0.0021 (7)
C6a0.0301 (9)0.0306 (9)0.0261 (9)0.0125 (7)0.0053 (7)0.0016 (7)
Geometric parameters (Å, º) top
O1b—C1b1.284 (2)N1a—C2a1.376 (3)
O2b—C7b1.308 (2)N2a—C1a1.348 (2)
O2b—H2b0.9820 (12)N2a—C3a1.375 (2)
O3b—C7b1.222 (2)N2a—C4a1.4622 (19)
O4b—N2b1.232 (2)N3a—C6a1.483 (2)
O5b—N2b1.2248 (17)N3a—H3aa0.9042 (14)
O6b—N1b1.2313 (18)N3a—H3ab0.9009 (13)
O7b—N1b1.225 (2)N3a—H3ac0.8932 (14)
N1b—C6b1.464 (2)C1a—H1a0.95
N2b—C4b1.458 (2)C2a—H2a0.95
C1b—C2b1.440 (2)C2a—C3a1.351 (2)
C1b—C6b1.428 (2)C3a—H3a0.95
C2b—C3b1.373 (2)C4a—H4aa0.99
C2b—C7b1.496 (2)C4a—H4ab0.99
C3b—H3b0.95C4a—C5a1.517 (2)
C3b—C4b1.382 (2)C5a—H5aa0.99
C4b—C5b1.378 (2)C5a—H5ab0.99
C5b—H5b0.95C5a—C6a1.507 (2)
C5b—C6b1.378 (2)C6a—H6aa0.99
N1a—C1a1.318 (2)C6a—H6ab0.99
C1b—O1b—H2b99.82 (10)C6a—N3a—H3ab109.46 (13)
C7b—O2b—H2b106.90 (11)C6a—N3a—H3ac111.76 (15)
O6b—N1b—O7b123.30 (15)H3aa—N3a—H3ab110.21 (16)
O6b—N1b—C6b117.72 (16)H3aa—N3a—H3ac106.71 (14)
O7b—N1b—C6b118.97 (13)H3ab—N3a—H3ac107.27 (13)
O4b—N2b—O5b123.59 (16)N1a—C1a—N2a111.91 (16)
O4b—N2b—C4b117.89 (12)N1a—C1a—H1a124.04
O5b—N2b—C4b118.52 (14)N2a—C1a—H1a124.04
O1b—C1b—C2b120.19 (13)N1a—C2a—H2a124.86
O1b—C1b—C6b124.76 (15)N1a—C2a—C3a110.28 (15)
C2b—C1b—C6b115.00 (15)H2a—C2a—C3a124.86
C1b—C2b—C3b121.54 (13)N2a—C3a—C2a106.10 (16)
C1b—C2b—C7b119.88 (15)N2a—C3a—H3a126.95
C3b—C2b—C7b118.56 (14)C2a—C3a—H3a126.95
C2b—C3b—H3b120.01N2a—C4a—H4aa109.47
C2b—C3b—C4b119.99 (15)N2a—C4a—H4ab109.47
H3b—C3b—C4b120.01N2a—C4a—C5a112.62 (14)
N2b—C4b—C3b119.03 (14)H4aa—C4a—H4ab106.12
N2b—C4b—C5b119.24 (13)H4aa—C4a—C5a109.47
C3b—C4b—C5b121.73 (16)H4ab—C4a—C5a109.47
C4b—C5b—H5b120.69C4a—C5a—H5aa109.47
C4b—C5b—C6b118.62 (13)C4a—C5a—H5ab109.47
H5b—C5b—C6b120.69C4a—C5a—C6a111.50 (15)
N1b—C6b—C1b120.26 (15)H5aa—C5a—H5ab107.36
N1b—C6b—C5b116.59 (13)H5aa—C5a—C6a109.47
C1b—C6b—C5b123.09 (15)H5ab—C5a—C6a109.47
O2b—C7b—O3b121.86 (14)N3a—C6a—C5a112.35 (15)
O2b—C7b—C2b115.78 (14)N3a—C6a—H6aa109.47
O3b—C7b—C2b122.33 (16)N3a—C6a—H6ab109.47
C1a—N1a—C2a105.01 (14)C5a—C6a—H6aa109.47
C1a—N2a—C3a106.69 (13)C5a—C6a—H6ab109.47
C1a—N2a—C4a125.73 (15)H6aa—C6a—H6ab106.43
C3a—N2a—C4a127.56 (14)O1b—H2b—O2b156.29 (9)
C6a—N3a—H3aa111.33 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4a—H4aa···O4bi0.992.533.359 (2)141
O2b—H2b···O1b0.9820 (12)1.5161 (11)2.4473 (16)156.29 (9)
O2b—H2b···C1b0.9820 (12)2.1471 (15)2.7833 (18)121.00 (8)
N3a—H3aa···N1aii0.9042 (14)1.9318 (14)2.797 (2)159.6 (1)
N3a—H3ab···O2biii0.9009 (13)2.5650 (12)3.1297 (17)121.35 (10)
N3a—H3ab···O3biii0.9009 (13)2.0721 (11)2.9537 (17)165.79 (10)
N3a—H3ac···O1biv0.8932 (14)2.0610 (13)2.815 (2)141.47 (11)
N3a—H3ac···O7biv0.8932 (14)2.4844 (13)2.9712 (19)114.74 (8)
Symmetry codes: (i) x+1, y+1, z; (ii) x, y, z; (iii) x+1, y, z; (iv) x, y+1, z+1.
4-{[(5-Methylisoxazol-3-yl)amino]sulfonyl}anilinium 2-hydroxy-3,5-dinitrobenzoate (TUJPEV) top
Crystal data top
C10H12N3O3S+·C7H3N2O7Z = 2
Mr = 481.41F(000) = 496
Triclinic, P1Dx = 1.609 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.5551 (1) ÅCell parameters from 6718 reflections
b = 10.5000 (2) Åθ = 1.8–32.6°
c = 12.7576 (3) ŵ = 0.23 mm1
α = 106.463 (1)°T = 296 K
β = 100.913 (1)°Prism, yellow
γ = 108.272 (1)°0.20 × 0.20 × 0.16 mm
V = 993.72 (3) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
6717 independent reflections
Radiation source: fine-focus sealed tube4398 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.030
ω and φ scanθmax = 32.6°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1212
Tmin = 0.955, Tmax = 0.964k = 1515
24261 measured reflectionsl = 1916
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F > 3σ(F)] = 0.044Hydrogen site location: difference Fourier map
wR(F) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.95Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
6717 reflections(Δ/σ)max = 0.013
301 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.35 e Å3
48 constraints
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Number of fixed parameters: 9

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.02012 (4)0.65156 (4)0.38514 (3)0.03475 (15)
O10.12136 (12)0.56298 (10)0.26952 (9)0.0472 (5)
O20.09555 (13)0.65440 (11)0.47594 (9)0.0468 (5)
O30.47434 (14)0.55510 (13)0.32058 (11)0.0626 (6)
N10.29155 (15)1.24477 (12)0.38430 (11)0.0434 (6)
N20.13845 (14)0.60248 (12)0.42019 (10)0.0376 (5)
N30.39246 (16)0.57705 (15)0.40555 (12)0.0536 (6)
C10.07464 (15)0.82919 (13)0.38935 (12)0.0322 (5)
C20.21693 (19)0.93183 (16)0.47844 (13)0.0511 (7)
C30.28732 (19)1.06857 (16)0.47796 (14)0.0514 (7)
C40.21467 (16)1.10142 (13)0.38945 (12)0.0344 (6)
C50.07052 (18)1.00124 (15)0.30229 (13)0.0444 (7)
C60.00046 (17)0.86380 (15)0.30181 (13)0.0421 (6)
C70.24788 (17)0.58299 (13)0.35471 (13)0.0355 (6)
C80.2306 (2)0.56568 (16)0.23936 (14)0.0473 (7)
C90.3761 (2)0.55015 (16)0.22381 (16)0.0511 (8)
C100.4452 (3)0.5287 (2)0.12416 (18)0.0766 (11)
O40.51685 (14)0.76882 (14)0.75724 (10)0.0657 (6)
O50.25004 (13)0.72390 (11)0.65907 (9)0.0495 (5)
O60.03442 (11)0.74382 (11)0.75483 (8)0.0431 (4)
O70.13539 (17)0.8490 (2)0.89544 (14)0.0980 (10)
O80.12065 (16)0.7660 (2)1.03000 (12)0.0975 (9)
O90.46550 (16)0.90412 (15)1.25865 (10)0.0717 (7)
O100.66293 (15)0.90569 (15)1.17611 (11)0.0749 (7)
N40.06158 (16)0.80710 (17)0.96062 (13)0.0598 (7)
N50.51466 (16)0.88865 (13)1.17407 (12)0.0488 (6)
C110.31789 (15)0.78551 (13)0.85956 (12)0.0326 (5)
C120.14714 (16)0.77857 (13)0.85292 (12)0.0328 (5)
C130.10840 (16)0.80786 (15)0.95755 (13)0.0389 (6)
C140.22578 (17)0.84024 (15)1.06095 (13)0.0403 (6)
C150.38931 (16)0.84763 (14)1.06263 (12)0.0365 (6)
C160.43735 (16)0.82163 (13)0.96389 (12)0.0356 (6)
C170.36856 (18)0.75728 (15)0.75210 (13)0.0400 (6)
H1a0.1888481.2565720.3422130.088 (4)*
H1b0.3535681.2974120.4468230.088 (4)*
H1c0.3482881.2386270.3382320.088 (4)*
H20.2651210.9087890.5385670.0613*
H2a0.1864990.6300390.502340.068 (5)*
H30.3839071.1384390.5375610.0617*
H50.0202221.0257660.2438150.0533*
H60.0967980.7945380.2424170.0506*
H80.1396150.5650540.1858780.0568*
H10a0.5519470.6085970.1422860.1149*
H10b0.3629550.5225510.0583210.1149*
H10c0.465050.4410640.10770.1149*
H140.1949650.8567421.1281710.0484*
H160.5493530.828330.9673860.0428*
H6a0.1155770.7276990.690230.132 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.03683 (17)0.03321 (18)0.0360 (2)0.01370 (13)0.01260 (14)0.01423 (16)
O10.0462 (5)0.0373 (5)0.0422 (7)0.0089 (4)0.0009 (5)0.0087 (5)
O20.0524 (6)0.0510 (6)0.0532 (7)0.0246 (5)0.0309 (5)0.0276 (6)
O30.0518 (6)0.0718 (8)0.0660 (9)0.0313 (6)0.0248 (6)0.0153 (7)
N10.0510 (7)0.0374 (6)0.0502 (9)0.0178 (5)0.0268 (6)0.0202 (6)
N20.0476 (6)0.0413 (6)0.0327 (7)0.0235 (5)0.0154 (5)0.0169 (6)
N30.0495 (7)0.0628 (9)0.0487 (9)0.0283 (6)0.0154 (6)0.0136 (7)
C10.0350 (6)0.0317 (7)0.0316 (8)0.0143 (5)0.0112 (5)0.0120 (6)
C20.0588 (9)0.0433 (9)0.0382 (9)0.0107 (7)0.0053 (7)0.0197 (8)
C30.0520 (9)0.0380 (8)0.0432 (10)0.0029 (7)0.0033 (7)0.0129 (8)
C40.0400 (7)0.0320 (7)0.0393 (9)0.0172 (6)0.0208 (6)0.0153 (6)
C50.0478 (8)0.0446 (8)0.0438 (10)0.0195 (7)0.0064 (7)0.0235 (8)
C60.0392 (7)0.0397 (8)0.0403 (9)0.0118 (6)0.0004 (6)0.0159 (7)
C70.0414 (7)0.0275 (7)0.0374 (9)0.0132 (5)0.0131 (6)0.0113 (6)
C80.0553 (9)0.0506 (9)0.0426 (10)0.0238 (7)0.0203 (7)0.0194 (8)
C90.0605 (9)0.0379 (8)0.0574 (12)0.0169 (7)0.0325 (9)0.0141 (8)
C100.0921 (14)0.0731 (13)0.0819 (15)0.0351 (12)0.0607 (13)0.0275 (13)
O40.0483 (6)0.0981 (10)0.0513 (8)0.0274 (6)0.0254 (5)0.0227 (7)
O50.0578 (6)0.0613 (7)0.0295 (6)0.0241 (5)0.0132 (5)0.0156 (5)
O60.0404 (5)0.0525 (6)0.0322 (6)0.0196 (4)0.0028 (4)0.0136 (5)
O70.0700 (8)0.1711 (16)0.0831 (11)0.0810 (10)0.0212 (8)0.0529 (11)
O80.0537 (7)0.1721 (16)0.0566 (9)0.0299 (9)0.0287 (7)0.0359 (10)
O90.0770 (8)0.0950 (10)0.0308 (7)0.0267 (7)0.0041 (6)0.0211 (7)
O100.0480 (7)0.0991 (10)0.0639 (9)0.0302 (6)0.0064 (6)0.0241 (8)
N40.0396 (7)0.0856 (11)0.0419 (9)0.0249 (7)0.0082 (6)0.0084 (8)
N50.0478 (7)0.0458 (7)0.0405 (9)0.0147 (6)0.0044 (6)0.0138 (7)
C110.0346 (6)0.0281 (6)0.0318 (8)0.0107 (5)0.0078 (5)0.0096 (6)
C120.0351 (6)0.0301 (7)0.0291 (8)0.0112 (5)0.0039 (5)0.0104 (6)
C130.0330 (6)0.0444 (8)0.0356 (9)0.0154 (6)0.0079 (6)0.0108 (7)
C140.0424 (7)0.0454 (8)0.0301 (8)0.0162 (6)0.0100 (6)0.0112 (7)
C150.0370 (7)0.0341 (7)0.0297 (8)0.0107 (5)0.0009 (6)0.0104 (6)
C160.0321 (6)0.0324 (7)0.0393 (9)0.0124 (5)0.0061 (6)0.0120 (6)
C170.0411 (7)0.0393 (8)0.0385 (9)0.0139 (6)0.0130 (6)0.0143 (7)
Geometric parameters (Å, º) top
S1—O11.4228 (9)C9—C101.491 (3)
S1—O21.4264 (13)C10—H10a0.96
S1—N21.6264 (14)C10—H10b0.96
O3—N31.402 (2)C10—H10c0.96
O3—C91.333 (2)O4—C171.223 (2)
N1—C41.468 (2)O5—C171.2827 (18)
N1—H1a1.0015 (14)O5—H6a1.2945 (12)
N1—H1b0.7932 (11)O6—C121.3010 (16)
N1—H1c0.8315 (15)O6—H6a1.1837 (11)
N2—C71.391 (2)O7—N41.211 (3)
N2—H2a0.9703 (12)O8—N41.214 (2)
N3—C71.312 (2)O9—N51.218 (2)
C1—C21.3764 (15)O10—N51.218 (2)
C1—C61.374 (2)N4—C131.460 (2)
C2—C31.374 (2)N5—C151.4638 (19)
C2—H20.93C11—C121.425 (2)
C3—C41.367 (2)C11—C161.3841 (19)
C3—H30.93C11—C171.493 (2)
C4—C51.3668 (15)C12—C131.409 (2)
C5—C61.376 (2)C13—C141.376 (2)
C5—H50.93C14—C151.372 (2)
C6—H60.93C14—H140.93
C7—C81.403 (2)C15—C161.379 (2)
C8—C91.348 (3)C16—H160.93
C8—H80.93
O1—S1—O2120.50 (6)C8—C9—C10133.88 (19)
O1—S1—N2108.78 (6)C9—C10—H10a109.47
O2—S1—N2104.15 (7)C9—C10—H10b109.47
N3—O3—C9108.94 (14)C9—C10—H10c109.47
C4—N1—H1a102.59 (10)H10a—C10—H10b109.47
C4—N1—H1b107.06 (15)H10a—C10—H10c109.47
C4—N1—H1c107.83 (13)H10b—C10—H10c109.47
H1a—N1—H1b124.65 (16)C17—O5—H6a105.28 (11)
H1a—N1—H1c103.41 (14)C12—O6—H6a102.01 (10)
H1b—N1—H1c110.21 (14)O7—N4—O8123.34 (17)
S1—N2—C7124.43 (12)O7—N4—C13118.74 (17)
S1—N2—H2a113.65 (11)O8—N4—C13117.91 (17)
C7—N2—H2a116.39 (12)O9—N5—O10124.03 (14)
O3—N3—C7104.86 (14)O9—N5—C15118.56 (14)
C2—C1—C6120.38 (14)O10—N5—C15117.41 (15)
C1—C2—C3119.57 (16)C12—C11—C16120.99 (14)
C1—C2—H2120.22C12—C11—C17118.93 (12)
C3—C2—H2120.22C16—C11—C17120.07 (13)
C2—C3—C4119.68 (12)O6—C12—C11121.05 (14)
C2—C3—H3120.16O6—C12—C13122.90 (13)
C4—C3—H3120.16C11—C12—C13116.03 (12)
N1—C4—C3120.80 (10)N4—C13—C12120.40 (13)
N1—C4—C5118.09 (15)N4—C13—C14116.57 (15)
C3—C4—C5121.09 (14)C12—C13—C14123.02 (14)
C4—C5—C6119.44 (16)C13—C14—C15118.50 (15)
C4—C5—H5120.28C13—C14—H14120.75
C6—C5—H5120.28C15—C14—H14120.75
C1—C6—C5119.80 (11)N5—C15—C14117.72 (14)
C1—C6—H6120.1N5—C15—C16120.43 (13)
C5—C6—H6120.1C14—C15—C16121.82 (13)
N2—C7—N3117.05 (14)C11—C16—C15119.61 (13)
N2—C7—C8131.01 (14)C11—C16—H16120.19
N3—C7—C8111.93 (15)C15—C16—H16120.19
C7—C8—C9104.20 (16)O4—C17—O5124.29 (16)
C7—C8—H8127.9O4—C17—C11119.59 (13)
C9—C8—H8127.9O5—C17—C11116.11 (13)
O3—C9—C8110.05 (18)O5—H6a—O6156.58 (6)
O3—C9—C10116.07 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1a···O6i1.0015 (14)2.0683 (10)3.0655 (17)173.55 (7)
N1—H1b···N3ii0.7932 (11)2.2920 (11)3.0393 (15)157.33 (11)
N1—H1c···O4ii0.8315 (15)1.8318 (14)2.663 (2)177.12 (7)
N2—H2a···O50.9703 (12)1.8440 (10)2.7852 (15)162.64 (9)
O5—H6a···O61.2945 (12)1.1837 (11)2.4268 (16)156.58 (6)
O5—H6a···C121.2945 (12)1.9326 (15)2.7490 (19)115.40 (6)
O6—H6a···O51.1837 (11)1.2945 (12)2.4268 (16)156.58 (6)
O6—H6a···C171.1837 (11)2.0485 (15)2.8249 (19)119.42 (7)
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+2, z+1.
2-Isopropyl-6-methyl-4-oxo-3,4-dihydropyrimidin-1-ium 2-carboxy-4,6-dinitrophenolate monohydrate (VABZIJ) top
Crystal data top
C8H13N2O+·C7H3N2O7·H2OZ = 2
Mr = 398.33F(000) = 416
Triclinic, P1Dx = 1.497 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.6691 (3) ÅCell parameters from 6994 reflections
b = 11.3831 (4) Åθ = 2.4–31.6°
c = 12.2900 (5) ŵ = 0.13 mm1
α = 89.727 (2)°T = 100 K
β = 76.771 (2)°Block, yellow
γ = 76.930 (2)°0.52 × 0.13 × 0.10 mm
V = 883.62 (6) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
4061 independent reflections
Radiation source: fine-focus sealed tube3042 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.030
φ and ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 88
Tmin = 0.937, Tmax = 0.987k = 1412
17014 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
R[F > 3σ(F)] = 0.038Secondary atom site location: difference Fourier map
wR(F) = 0.086Hydrogen site location: difference Fourier map
S = 1.77H atoms treated by a mixture of independent and constrained refinement
4061 reflectionsWeighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
258 parameters(Δ/σ)max = 0.014
0 restraintsΔρmax = 0.46 e Å3
52 constraintsΔρmin = 0.23 e Å3
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Number of fixed parameters: 15

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.30546 (16)0.17099 (9)0.14963 (8)0.0232 (4)
O20.56653 (17)0.35718 (9)0.01361 (9)0.0316 (4)
O30.48656 (18)0.36691 (9)0.14697 (9)0.0311 (4)
O40.36254 (16)0.00313 (9)0.33889 (8)0.0235 (4)
O50.23753 (16)0.16995 (9)0.24573 (8)0.0255 (4)
O60.07250 (15)0.19153 (8)0.16330 (8)0.0204 (4)
O70.14533 (16)0.02234 (9)0.25238 (8)0.0215 (4)
O80.31889 (16)0.38510 (9)0.41956 (8)0.0221 (4)
N10.30174 (18)0.05930 (11)0.25094 (10)0.0185 (4)
N20.48606 (19)0.31064 (11)0.06125 (10)0.0213 (4)
N30.11898 (17)0.64252 (10)0.66449 (9)0.0147 (4)
N40.23841 (17)0.58259 (10)0.47936 (9)0.0144 (4)
C10.3103 (2)0.11910 (12)0.05547 (11)0.0151 (5)
C20.3895 (2)0.18160 (12)0.05145 (11)0.0154 (5)
C30.3838 (2)0.12419 (13)0.15034 (12)0.0160 (5)
H3a0.4327430.1679180.2186860.0192*
C40.3044 (2)0.00126 (13)0.14615 (11)0.0150 (5)
C50.2281 (2)0.06626 (13)0.04539 (11)0.0148 (5)
H5a0.1769640.1494040.0446560.0177*
C60.2290 (2)0.00871 (12)0.05379 (11)0.0140 (5)
C70.1429 (2)0.08121 (13)0.16123 (11)0.0159 (5)
C80.2598 (2)0.45829 (12)0.49910 (12)0.0158 (5)
C90.2070 (2)0.43367 (13)0.61582 (11)0.0160 (5)
H9a0.2211910.3540140.6363870.0192*
C100.1376 (2)0.52320 (12)0.69587 (11)0.0157 (5)
C110.1694 (2)0.67095 (12)0.55875 (11)0.0141 (5)
C120.1445 (2)0.80006 (12)0.52928 (11)0.0153 (5)
H12a0.1103480.850570.5983710.0184*
C130.0374 (2)0.83589 (13)0.47019 (13)0.0224 (5)
H13a0.0549270.9193180.4526270.0335*
H13b0.1657590.8240460.5184620.0335*
H13c0.0057340.7867630.4024090.0335*
C140.3509 (2)0.82298 (12)0.45745 (12)0.0195 (5)
H14a0.4615270.8005480.4968970.0292*
H14b0.3315150.9070810.4422050.0292*
H14c0.3891040.7756880.388230.0292*
C150.0772 (2)0.50600 (13)0.81821 (12)0.0221 (5)
H15a0.0688940.5452230.8471260.0332*
H15b0.1638950.5403890.8554390.0332*
H15c0.0977930.4212950.8309530.0332*
O1w0.32852 (17)0.60955 (9)0.25340 (8)0.0272 (4)
H1n30.0614150.7068780.7226090.037 (5)*
H1n40.2704670.6022340.4067040.034 (5)*
H2w10.3397290.6751240.2107790.053 (6)*
H1w10.3816110.5399110.209320.055 (6)*
H70.2113640.0637540.2203310.078 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0305 (6)0.0178 (6)0.0185 (6)0.0038 (5)0.0018 (5)0.0031 (4)
O20.0431 (7)0.0219 (6)0.0232 (6)0.0045 (5)0.0063 (5)0.0044 (5)
O30.0489 (7)0.0181 (6)0.0229 (6)0.0036 (5)0.0053 (5)0.0086 (5)
O40.0291 (6)0.0274 (6)0.0138 (6)0.0083 (5)0.0030 (5)0.0009 (5)
O50.0347 (6)0.0178 (6)0.0235 (6)0.0045 (5)0.0072 (5)0.0058 (5)
O60.0244 (6)0.0142 (6)0.0187 (6)0.0013 (4)0.0004 (4)0.0029 (4)
O70.0284 (6)0.0175 (6)0.0140 (5)0.0009 (5)0.0003 (4)0.0003 (4)
O80.0321 (6)0.0137 (5)0.0176 (6)0.0026 (5)0.0027 (5)0.0025 (4)
N10.0182 (6)0.0202 (7)0.0186 (7)0.0071 (6)0.0047 (5)0.0034 (6)
N20.0240 (7)0.0161 (7)0.0198 (7)0.0035 (6)0.0019 (6)0.0001 (6)
N30.0168 (6)0.0123 (6)0.0136 (6)0.0024 (5)0.0017 (5)0.0006 (5)
N40.0172 (6)0.0117 (6)0.0129 (6)0.0026 (5)0.0014 (5)0.0011 (5)
C10.0133 (7)0.0177 (8)0.0148 (7)0.0064 (6)0.0014 (6)0.0022 (6)
C20.0158 (7)0.0118 (7)0.0176 (8)0.0030 (6)0.0017 (6)0.0008 (6)
C30.0159 (7)0.0184 (8)0.0140 (8)0.0070 (6)0.0012 (6)0.0029 (6)
C40.0146 (7)0.0196 (8)0.0125 (7)0.0073 (6)0.0030 (6)0.0033 (6)
C50.0121 (7)0.0137 (7)0.0188 (8)0.0046 (6)0.0026 (6)0.0007 (6)
C60.0113 (7)0.0154 (7)0.0154 (7)0.0048 (6)0.0015 (6)0.0005 (6)
C70.0130 (7)0.0171 (8)0.0170 (8)0.0048 (6)0.0008 (6)0.0000 (6)
C80.0145 (7)0.0132 (7)0.0193 (8)0.0022 (6)0.0036 (6)0.0001 (6)
C90.0177 (7)0.0110 (7)0.0187 (8)0.0031 (6)0.0036 (6)0.0032 (6)
C100.0137 (7)0.0154 (8)0.0182 (8)0.0033 (6)0.0041 (6)0.0029 (6)
C110.0106 (7)0.0152 (7)0.0161 (8)0.0028 (6)0.0026 (6)0.0012 (6)
C120.0178 (7)0.0114 (7)0.0155 (7)0.0034 (6)0.0014 (6)0.0007 (6)
C130.0218 (8)0.0140 (8)0.0321 (9)0.0033 (6)0.0089 (7)0.0052 (7)
C140.0210 (8)0.0141 (8)0.0218 (8)0.0048 (6)0.0012 (6)0.0004 (6)
C150.0269 (8)0.0194 (8)0.0188 (8)0.0047 (7)0.0034 (6)0.0019 (6)
O1w0.0471 (7)0.0134 (6)0.0163 (6)0.0043 (5)0.0005 (5)0.0003 (5)
Geometric parameters (Å, º) top
O1—C11.2939 (17)C4—C51.3881 (18)
O1—H71.4329 (9)C5—H5a0.93
O2—N21.2279 (17)C5—C61.3816 (19)
O3—N21.2346 (17)C6—C71.4844 (18)
O4—N11.2304 (15)C8—C91.439 (2)
O5—N11.2321 (15)C9—H9a0.93
O6—C71.2355 (16)C9—C101.3449 (19)
O7—C71.3040 (17)C10—C151.4889 (19)
O7—H71.0191 (9)C11—C121.4936 (19)
O8—C81.2198 (17)C12—H12a0.98
N1—C41.4597 (18)C12—C131.531 (2)
N2—C21.4576 (17)C12—C141.5318 (19)
N3—C101.3963 (18)C13—H13a0.96
N3—C111.3236 (17)C13—H13b0.96
N3—H1n30.9729 (11)C13—H13c0.96
N4—C81.4152 (18)C14—H14a0.96
N4—C111.3303 (17)C14—H14b0.96
N4—H1n40.9085 (11)C14—H14c0.96
C1—C21.4259 (18)C15—H15a0.96
C1—C61.4349 (19)C15—H15b0.96
C2—C31.381 (2)C15—H15c0.96
C3—H3a0.93O1w—H2w10.9169 (10)
C3—C41.3763 (19)O1w—H1w10.9146 (10)
C1—O1—H796.54 (8)N4—C8—C9113.60 (12)
C7—O7—H7101.27 (9)C8—C9—H9a119.24
O4—N1—O5124.04 (12)C8—C9—C10121.51 (13)
O4—N1—C4118.12 (11)H9a—C9—C10119.24
O5—N1—C4117.84 (11)N3—C10—C9118.95 (12)
O2—N2—O3123.42 (12)N3—C10—C15116.00 (11)
O2—N2—C2119.16 (12)C9—C10—C15125.06 (13)
O3—N2—C2117.39 (12)N3—C11—N4118.76 (12)
C10—N3—C11122.45 (11)N3—C11—C12120.45 (12)
C10—N3—H1n3118.37 (11)N4—C11—C12120.78 (12)
C11—N3—H1n3119.14 (11)C11—C12—H12a108.71
C8—N4—C11124.69 (12)C11—C12—C13109.61 (13)
C8—N4—H1n4116.55 (11)C11—C12—C14111.42 (10)
C11—N4—H1n4118.72 (12)H12a—C12—C13108.78
O1—C1—C2124.06 (12)H12a—C12—C14106.87
O1—C1—C6120.40 (11)C13—C12—C14111.36 (12)
C2—C1—C6115.53 (12)C12—C13—H13a109.47
N2—C2—C1120.85 (12)C12—C13—H13b109.47
N2—C2—C3116.56 (11)C12—C13—H13c109.47
C1—C2—C3122.58 (12)H13a—C13—H13b109.47
C2—C3—H3a120.52H13a—C13—H13c109.47
C2—C3—C4118.97 (12)H13b—C13—H13c109.47
H3a—C3—C4120.52C12—C14—H14a109.47
N1—C4—C3118.77 (12)C12—C14—H14b109.47
N1—C4—C5119.38 (12)C12—C14—H14c109.47
C3—C4—C5121.85 (13)H14a—C14—H14b109.47
C4—C5—H5a120.33H14a—C14—H14c109.47
C4—C5—C6119.34 (12)H14b—C14—H14c109.47
H5a—C5—C6120.33C10—C15—H15a109.47
C1—C6—C5121.71 (12)C10—C15—H15b109.47
C1—C6—C7119.30 (12)C10—C15—H15c109.47
C5—C6—C7118.99 (12)H15a—C15—H15b109.47
O6—C7—O7122.20 (12)H15a—C15—H15c109.47
O6—C7—C6121.26 (12)H15b—C15—H15c109.47
O7—C7—C6116.54 (12)H2w1—O1w—H1w1110.00 (10)
O8—C8—N4119.14 (12)O1—H7—O7165.94 (7)
O8—C8—C9127.26 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12a···O7i0.982.423.3068 (15)151
N3—H1n3···O6i0.9729 (11)1.7539 (9)2.7182 (14)170.48 (8)
N4—H1n4···O1w0.9085 (11)1.8401 (10)2.7348 (15)167.76 (8)
O1w—H2w1···O1ii0.9169 (10)1.8895 (10)2.7886 (14)166.21 (6)
O1w—H1w1···O3iii0.9146 (10)2.0399 (10)2.9352 (14)165.84 (7)
O7—H7···O11.0191 (9)1.4329 (9)2.4340 (13)165.94 (7)
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1, z; (iii) x+1, y, z.
1-Aza-8-azoniabicyclo[5.4.0]undec-7-ene 4-aminobenzoate (WADXOR) top
Crystal data top
C9H17N2+·C7H3N2O7F(000) = 800
Mr = 380.35Dx = 1.489 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yabcCell parameters from 1891 reflections
a = 6.1537 (3) Åθ = 3.5–26.6°
b = 19.1541 (14) ŵ = 0.12 mm1
c = 14.5527 (11) ÅT = 200 K
β = 98.343 (6)°Needle, yellow
V = 1697.2 (2) Å30.30 × 0.13 × 0.10 mm
Z = 4
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer
3339 independent reflections
Graphite monochromator1976 reflections with I > 3σ(I)
Detector resolution: 16.067 pixels mm-1Rint = 0.034
ω scansθmax = 26.0°, θmin = 3.4°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
h = 77
Tmin = 0.920, Tmax = 0.990k = 2323
7800 measured reflectionsl = 1717
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
S = 1.33(Δ/σ)max = 0.005
3339 reflectionsΔρmax = 0.36 e Å3
268 parametersΔρmin = 0.24 e Å3
2 restraintsExtinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
98 constraintsExtinction coefficient: 2200 (700)
Primary atom site location: structure-invariant direct methods
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Number of fixed parameters : 10

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O2b0.8418 (3)0.56169 (11)0.78950 (14)0.0440 (8)0.727 (4)
H61b0.8521070.5608190.767070.0359*0.273 (4)
O21b0.7735 (8)0.6569 (3)0.4912 (4)0.048 (2)0.273 (4)
H6b0.8057120.6449670.5072070.0328*0.727 (4)
O11b0.5083 (2)0.68884 (8)0.59278 (11)0.0444 (6)
O12b0.5447 (2)0.64534 (8)0.73586 (12)0.0524 (7)
O31b1.1108 (3)0.45706 (10)0.81717 (14)0.0829 (9)
O32b1.4073 (3)0.47245 (10)0.75770 (13)0.0775 (8)
O51b1.3288 (3)0.55869 (9)0.44602 (12)0.0603 (7)
O52b1.0707 (3)0.63212 (10)0.39870 (12)0.0680 (8)
N3b1.2111 (3)0.48284 (10)0.76049 (14)0.0472 (8)
N5b1.1654 (3)0.59180 (10)0.45701 (14)0.0418 (7)
C1b0.8002 (3)0.60956 (10)0.63903 (15)0.0264 (7)
C2b0.9062 (3)0.56604 (11)0.70954 (15)0.0299 (7)
C3b1.0952 (3)0.53063 (10)0.69140 (15)0.0309 (7)
C4b1.1814 (3)0.53946 (10)0.61042 (15)0.0309 (7)
C5b1.0736 (3)0.58234 (10)0.54290 (14)0.0271 (7)
C6b0.8810 (3)0.61681 (10)0.55538 (15)0.0273 (7)
C11b0.6030 (3)0.65080 (11)0.65583 (18)0.0351 (8)
N1a0.1521 (2)0.82026 (8)0.63826 (12)0.0293 (6)
N8a0.1721 (2)0.76019 (9)0.67283 (12)0.0373 (7)
C2a0.3261 (3)0.85089 (11)0.57022 (15)0.0370 (8)
C3a0.2602 (3)0.91805 (11)0.52679 (15)0.0401 (8)
C4a0.1188 (3)0.90791 (11)0.45061 (16)0.0417 (8)
C5a0.0933 (3)0.86805 (11)0.48032 (14)0.0401 (8)
C6a0.0611 (3)0.79367 (11)0.51423 (14)0.0344 (8)
C7a0.0226 (3)0.79087 (10)0.61288 (14)0.0268 (7)
C9a0.1394 (8)0.7480 (3)0.7694 (4)0.0377 (17)0.687 (4)
C10a0.0234 (5)0.8112 (2)0.8006 (2)0.0388 (12)0.687 (4)
C11a0.1865 (3)0.82334 (13)0.73606 (16)0.0375 (8)
C13a0.192 (2)0.7733 (6)0.7752 (10)0.0377 (17)0.313 (4)
C12a0.0453 (12)0.7700 (5)0.7962 (6)0.0388 (12)0.313 (4)
H4b1.3131230.5163930.6011440.0371*
H8a0.3040170.7430290.6527060.073 (8)*
H10a0.1195150.8525930.8003330.0466*0.686
H21a0.4583930.8592490.6001030.0444*
H22a0.3739110.8163720.5207730.0444*
H31a0.3935230.9448050.5020410.0481*
H32a0.1825750.9486580.5757160.0481*
H41a0.0845640.953950.4252850.0501*
H42a0.205390.8839820.3971030.0501*
H51a0.1805060.8667590.4282860.0482*
H52a0.1868380.8945380.529430.0482*
H61a0.1913560.7651120.5065610.0413*
H62a0.0639470.771620.4741770.0413*
H91a0.0461760.7061490.7725040.0452*0.687 (4)
H92a0.2838330.742650.8087120.0452*0.687 (4)
H11a0.0098730.8034390.8643510.0466*0.686
H12a0.318 (2)0.7965 (9)0.7425 (13)0.045*
H13a0.230 (3)0.8711 (6)0.7485 (13)0.045*
H14a0.1050820.72260.7824360.0466*0.313 (4)
H15a0.0473110.7807680.8625980.0466*0.313 (4)
H16a0.278930.7355190.8091310.0452*0.313 (4)
H17a0.2516970.8206860.7892370.0452*0.313 (4)
H21b0.6218370.6780520.5386280.082 (11)*0.273 (4)
H2b0.7028960.5982910.7744750.082 (11)*0.727 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O2b0.0481 (12)0.0570 (16)0.0296 (15)0.0087 (11)0.0152 (10)0.0091 (11)
O21b0.045 (3)0.053 (4)0.046 (4)0.006 (3)0.006 (3)0.023 (3)
O11b0.0369 (8)0.0391 (10)0.0583 (12)0.0136 (7)0.0102 (8)0.0073 (9)
O12b0.0488 (9)0.0643 (12)0.0488 (12)0.0091 (8)0.0232 (8)0.0030 (9)
O31b0.0796 (13)0.0853 (16)0.0753 (16)0.0256 (11)0.0175 (11)0.0533 (13)
O32b0.0728 (12)0.0903 (16)0.0642 (14)0.0483 (11)0.0074 (10)0.0050 (11)
O51b0.0542 (10)0.0650 (12)0.0694 (13)0.0077 (9)0.0350 (9)0.0110 (10)
O52b0.0926 (13)0.0722 (14)0.0455 (12)0.0171 (11)0.0314 (10)0.0241 (10)
N3b0.0575 (13)0.0347 (13)0.0432 (15)0.0005 (11)0.0137 (11)0.0004 (10)
N5b0.0476 (11)0.0400 (13)0.0414 (13)0.0046 (10)0.0193 (10)0.0067 (10)
C1b0.0265 (10)0.0220 (11)0.0303 (13)0.0029 (9)0.0024 (9)0.0023 (10)
C2b0.0337 (11)0.0267 (12)0.0294 (14)0.0061 (10)0.0050 (10)0.0023 (10)
C3b0.0361 (11)0.0233 (12)0.0304 (14)0.0002 (9)0.0053 (10)0.0025 (10)
C4b0.0257 (10)0.0240 (12)0.0413 (15)0.0013 (9)0.0005 (10)0.0053 (11)
C5b0.0295 (10)0.0254 (12)0.0274 (13)0.0052 (9)0.0073 (9)0.0017 (10)
C6b0.0298 (10)0.0218 (12)0.0290 (13)0.0028 (9)0.0003 (9)0.0007 (10)
C11b0.0297 (11)0.0296 (13)0.0464 (16)0.0042 (10)0.0070 (11)0.0061 (12)
N1a0.0249 (8)0.0327 (11)0.0305 (11)0.0026 (8)0.0041 (8)0.0000 (9)
N8a0.0332 (9)0.0493 (12)0.0291 (12)0.0137 (9)0.0037 (8)0.0056 (9)
C2a0.0243 (10)0.0400 (14)0.0451 (15)0.0063 (10)0.0002 (10)0.0020 (12)
C3a0.0374 (12)0.0331 (14)0.0465 (16)0.0071 (10)0.0044 (11)0.0000 (11)
C4a0.0450 (12)0.0397 (15)0.0370 (15)0.0028 (11)0.0060 (11)0.0087 (11)
C5a0.0368 (11)0.0526 (16)0.0319 (14)0.0008 (11)0.0079 (10)0.0091 (12)
C6a0.0355 (11)0.0411 (15)0.0262 (13)0.0079 (10)0.0032 (9)0.0057 (11)
C7a0.0283 (10)0.0224 (12)0.0291 (13)0.0012 (9)0.0025 (9)0.0030 (10)
C9a0.040 (3)0.041 (4)0.0304 (18)0.001 (2)0.001 (2)0.004 (3)
C10a0.049 (2)0.042 (2)0.0270 (17)0.0043 (18)0.0083 (15)0.0029 (19)
C11a0.0367 (12)0.0426 (15)0.0364 (15)0.0003 (11)0.0161 (11)0.0056 (12)
C13a0.040 (3)0.041 (4)0.0304 (18)0.001 (2)0.001 (2)0.004 (3)
C12a0.049 (2)0.042 (2)0.0270 (17)0.0043 (18)0.0083 (15)0.0029 (19)
Geometric parameters (Å, º) top
O2b—C2b1.285 (3)C2a—H22a0.99
O2b—H2b1.103 (2)C3a—C4a1.518 (3)
H61b—C2b0.95C3a—H31a0.99
O21b—C6b1.311 (6)C3a—H32a0.99
O21b—H21b1.303 (6)C4a—C5a1.520 (3)
H6b—C6b0.95C4a—H41a0.99
O11b—C11b1.248 (3)C4a—H42a0.99
O11b—H21b1.1454 (16)C5a—C6a1.530 (3)
O12b—C11b1.272 (3)C5a—H51a0.99
O12b—H2b1.3846 (15)C5a—H52a0.99
O31b—N3b1.205 (3)C6a—C7a1.490 (3)
O32b—N3b1.230 (3)C6a—H61a0.99
O51b—N5b1.219 (3)C6a—H62a0.99
O52b—N5b1.230 (3)C9a—C10a1.508 (6)
N3b—C3b1.466 (3)C9a—C13a0.581 (13)
N5b—C5b1.456 (3)C9a—C12a1.323 (10)
C1b—C2b1.407 (3)C9a—H91a0.99
C1b—C6b1.387 (3)C9a—H92a0.99
C1b—C11b1.497 (3)C9a—H16a0.9922
C2b—C3b1.404 (3)C10a—C11a1.501 (4)
C3b—C4b1.371 (3)C10a—C13a1.358 (14)
C4b—C5b1.375 (3)C10a—H10a0.99
C4b—H4b0.95C10a—H11a0.99
C5b—C6b1.392 (3)C10a—H15a1.207
N1a—C2a1.471 (2)C11a—C12a1.530 (8)
N1a—C7a1.313 (2)C11a—H12a0.977 (15)
N1a—C11a1.470 (3)C11a—H13a0.978 (13)
N8a—C7a1.311 (2)C13a—C12a1.534 (16)
N8a—C9a1.467 (6)C13a—H92a0.9083
N8a—C13a1.498 (15)C13a—H16a0.99
N8a—H8a0.9604 (17)C13a—H17a0.99
C2a—C3a1.514 (3)C12a—H14a0.99
C2a—H21a0.99C12a—H15a0.99
H6b—O21b—H21b102.88N8a—C9a—C13a81.6 (16)
C11b—O12b—H2b98.61 (14)N8a—C9a—C12a118.3 (5)
O31b—N3b—O32b124.0 (2)N8a—C9a—H91a109.47
O31b—N3b—C3b118.6 (2)N8a—C9a—H92a109.47
O32b—N3b—C3b117.4 (2)N8a—C9a—H14a114.78
O51b—N5b—O52b123.6 (2)N8a—C9a—H16a111.65
O51b—N5b—C5b118.57 (18)C10a—C9a—H91a109.47
O52b—N5b—C5b117.83 (18)C10a—C9a—H92a109.47
C2b—C1b—C6b120.82 (17)C13a—C9a—C12a99.9 (15)
C2b—C1b—C11b119.6 (2)C13a—C9a—H91a168.74
C6b—C1b—C11b119.51 (18)C13a—C9a—H14a137.56
O2b—C2b—C1b121.84 (19)C12a—C9a—H92a126.91
O2b—C2b—C3b120.77 (19)C12a—C9a—H16a127.82
H61b—C2b—C1b121.37H91a—C9a—H92a111.59
H61b—C2b—C3b121.37H14a—C9a—H16a126.91
C1b—C2b—C3b117.3 (2)H14a—C9a—H17a129.78
N3b—C3b—C2b120.4 (2)H16a—C9a—H17a77.55
N3b—C3b—C4b117.12 (18)C9a—C10a—C11a109.8 (3)
C2b—C3b—C4b122.44 (18)C11a—C10a—C13a122.2 (6)
C3b—C4b—C5b118.75 (18)C11a—C10a—H10a109.47
C3b—C4b—H4b120.62C11a—C10a—H11a109.47
C5b—C4b—H4b120.62C11a—C10a—H17a132.02
N5b—C5b—C4b118.74 (17)C13a—C10a—H11a116.43
N5b—C5b—C6b119.80 (17)C13a—C10a—H15a108.54
C4b—C5b—C6b121.5 (2)C12a—C10a—H17a124.07
O21b—C6b—C1b118.4 (3)H10a—C10a—H11a109.16
O21b—C6b—C5b122.4 (3)H10a—C10a—H15a132.06
H6b—C6b—C1b120.41H11a—C10a—H17a117.48
H6b—C6b—C5b120.41H15a—C10a—H17a127.34
C1b—C6b—C5b119.17 (18)N1a—C11a—C10a111.6 (2)
O11b—C11b—O12b123.9 (2)N1a—C11a—C12a112.2 (4)
O11b—C11b—C1b119.4 (2)N1a—C11a—H12a108.1 (11)
O12b—C11b—C1b116.70 (19)N1a—C11a—H13a107.3 (12)
C2a—N1a—C7a121.83 (17)C10a—C11a—H12a120.7 (10)
C2a—N1a—C11a116.29 (16)C10a—C11a—H13a105.2 (10)
C7a—N1a—C11a121.87 (16)C12a—C11a—H13a131.8 (11)
C7a—N8a—C9a121.9 (2)H12a—C11a—H13a102.9 (15)
C7a—N8a—C13a122.3 (5)N8a—C13a—C9a75.8 (15)
C7a—N8a—H8a119.53 (19)N8a—C13a—C10a114.0 (9)
C9a—N8a—C13a22.6 (5)N8a—C13a—C12a104.5 (8)
C9a—N8a—H8a118.5 (2)N8a—C13a—H10a113.12
C13a—N8a—H8a114.3 (5)N8a—C13a—H92a112.32
N1a—C2a—C3a114.01 (15)N8a—C13a—H16a109.47
N1a—C2a—H21a109.47N8a—C13a—H17a109.47
N1a—C2a—H22a109.47C9a—C13a—H10a130.08
C3a—C2a—H21a109.47C9a—C13a—H17a167.66
C3a—C2a—H22a109.47C10a—C13a—H92a129.79
H21a—C2a—H22a104.52C10a—C13a—H16a129.35
C2a—C3a—C4a114.39 (18)C12a—C13a—H92a113.84
C2a—C3a—H31a109.47C12a—C13a—H16a109.47
C2a—C3a—H32a109.47C12a—C13a—H17a109.47
C4a—C3a—H31a109.47H10a—C13a—H91a126.53
C4a—C3a—H32a109.47H10a—C13a—H92a130.35
H31a—C3a—H32a104.05H10a—C13a—H16a135.32
C3a—C4a—C5a114.58 (18)H92a—C13a—H17a107.21
C3a—C4a—H41a109.47H16a—C13a—H17a114.05
C3a—C4a—H42a109.47C9a—C12a—C11a119.1 (6)
C5a—C4a—H41a109.47C9a—C12a—H11a111.16
C5a—C4a—H42a109.47C9a—C12a—H15a119.13
H41a—C4a—H42a103.83C10a—C12a—H91a125.59
C4a—C5a—C6a114.44 (16)C10a—C12a—H14a169.66
C4a—C5a—H51a109.47C11a—C12a—C13a109.6 (7)
C4a—C5a—H52a109.47C11a—C12a—H91a130.75
C6a—C5a—H51a109.47C11a—C12a—H14a109.47
C6a—C5a—H52a109.47C11a—C12a—H15a109.47
H51a—C5a—H52a104C13a—C12a—H14a109.47
C5a—C6a—C7a112.99 (17)C13a—C12a—H15a109.47
C5a—C6a—H61a109.47H91a—C12a—H11a130.35
C5a—C6a—H62a109.47H91a—C12a—H15a118.71
C7a—C6a—H61a109.47H11a—C12a—H14a133.54
C7a—C6a—H62a109.47H14a—C12a—H15a109.31
H61a—C6a—H62a105.71O21b—H21b—O11b167.3 (3)
N1a—C7a—N8a121.93 (19)H6b—H21b—O11b152.98
N1a—C7a—C6a120.45 (16)O2b—H2b—O12b166.81 (13)
N8a—C7a—C6a117.59 (17)H61b—H2b—O12b150.18
N8a—C9a—C10a107.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8a—H8a···O11b0.9604 (17)1.9329 (15)2.864 (2)162.83 (11)
C10a—H10a···O32bi0.992.443.248 (4)138
C2a—H21a···O31bii0.992.483.275 (3)137
C6a—H62a···O21biii0.992.443.152 (6)128
C10a—H11a···O21biv0.992.473.033 (7)116
O21b—H21b···O11b1.303 (6)1.1454 (16)2.433 (6)167.3 (3)
O11b—H21b···O21b1.1454 (16)1.303 (6)2.433 (6)167.3 (3)
O12b—H2b···O2b1.3846 (15)1.103 (2)2.471 (2)166.81 (13)
Symmetry codes: (i) x+3/2, y+1/2, z+3/2; (ii) x+1/2, y+1/2, z+3/2; (iii) x1, y, z; (iv) x1/2, y+3/2, z+1/2.
4-(Diphenylmethyl)-1-(3-phenylprop-2-en-1-yl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate (YAXPOE) top
Crystal data top
C26H29N2+·C7H3N2O7F(000) = 1256
Mr = 596.63Dx = 1.341 Mg m3
Monoclinic, P21/cMelting point: 383 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 14.5648 (3) ÅCell parameters from 9909 reflections
b = 12.9374 (3) Åθ = 2.3–28.3°
c = 16.1619 (3) ŵ = 0.10 mm1
β = 103.900 (1)°T = 200 K
V = 2956.22 (11) Å3Block, yellow
Z = 40.51 × 0.26 × 0.17 mm
Data collection top
Bruker APEXII CCD
diffractometer
7344 independent reflections
Radiation source: fine-focus sealed tube5724 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.015
φ and ω scansθmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1919
Tmin = 0.932, Tmax = 1.000k = 1717
29552 measured reflectionsl = 2115
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F > 3σ(F)] = 0.054Hydrogen site location: difference Fourier map
wR(F) = 0.190H atoms treated by a mixture of independent and constrained refinement
S = 1.80Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0063999998I2)
7344 reflections(Δ/σ)max = 0.044
399 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = 0.28 e Å3
120 constraints
Special details top

Refinement. Number of fixed parameters 6

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.25627 (8)0.71181 (9)0.31343 (7)0.0246 (3)
H710.301280.6694740.3499790.035 (4)*
N20.10023 (8)0.56683 (9)0.26575 (7)0.0233 (3)
C10.29865 (11)0.95151 (12)0.41661 (10)0.0334 (5)
H1a0.2458980.9809320.3774220.0401*
C20.33463 (11)0.86695 (12)0.39170 (10)0.0322 (5)
H20.3867650.8354780.4302020.0386*
C30.29839 (12)0.81754 (12)0.30656 (10)0.0333 (5)
H3a0.3505210.8113910.277250.04*
H3b0.2500480.8627410.2705140.04*
C40.17112 (10)0.71678 (11)0.34935 (9)0.0281 (4)
H4a0.1232410.7627040.3135660.0337*
H4b0.1890390.7458970.407670.0337*
C50.12943 (10)0.61031 (11)0.35226 (9)0.0271 (4)
H5a0.073870.6148050.3773370.0326*
H5b0.1771610.5645220.3883860.0326*
C60.18571 (10)0.55563 (11)0.23345 (9)0.0262 (4)
H6a0.2311710.5096060.2718160.0315*
H6b0.1689310.52330.1762720.0315*
C70.23149 (10)0.65944 (12)0.22789 (9)0.0282 (4)
H7a0.2895370.6498130.2070680.0338*
H7b0.1876390.7038270.1864930.0338*
C80.05326 (9)0.46528 (10)0.26756 (8)0.0230 (4)
H80.0992820.4172660.3045420.0276*
C110.33145 (11)1.00535 (12)0.49876 (10)0.0326 (5)
C120.41578 (13)0.97941 (14)0.55685 (10)0.0391 (5)
H120.4549270.9265170.5432050.047*
C130.44278 (15)1.03053 (17)0.63457 (11)0.0502 (6)
H130.4997991.0116580.6740940.0603*
C140.38752 (17)1.10810 (17)0.65451 (12)0.0554 (7)
H140.406881.1431580.7074950.0665*
C150.30389 (15)1.13552 (16)0.59798 (13)0.0516 (7)
H150.2658491.189310.611970.0619*
C160.27570 (13)1.08400 (13)0.52053 (11)0.0397 (5)
H160.2178821.1024360.4819490.0476*
C210.03166 (9)0.47504 (10)0.30647 (8)0.0240 (4)
C220.04272 (11)0.40385 (12)0.36763 (10)0.0315 (5)
H220.0032760.3511980.3853150.0378*
C230.12077 (12)0.40899 (13)0.40333 (11)0.0388 (5)
H230.1277450.3598260.4450560.0466*
C240.18805 (12)0.48544 (13)0.37818 (11)0.0385 (5)
H240.2416770.4883650.4019110.0461*
C250.17687 (11)0.55719 (12)0.31859 (11)0.0351 (5)
H250.2227110.6101740.3017380.0421*
C260.09910 (10)0.55304 (11)0.28271 (9)0.0286 (4)
H260.0918990.6033960.2419580.0344*
C310.02520 (10)0.41880 (11)0.17810 (9)0.0248 (4)
C320.06690 (11)0.32720 (12)0.16027 (10)0.0331 (5)
H320.1124960.29380.2040430.0397*
C330.04254 (13)0.28416 (13)0.07918 (11)0.0392 (5)
H330.0718420.2218930.0677980.047*
C340.02351 (12)0.33108 (13)0.01557 (10)0.0379 (5)
H340.0396380.3018860.0399790.0455*
C350.06672 (12)0.42142 (14)0.03267 (10)0.0385 (5)
H350.1137090.4532380.010920.0461*
C360.04162 (11)0.46550 (12)0.11316 (10)0.0321 (5)
H360.0704830.5283110.1239290.0386*
O10.63327 (8)0.37352 (10)0.53505 (8)0.0392 (4)
O20.58197 (10)0.44006 (14)0.67133 (9)0.0614 (6)
O30.43608 (10)0.48129 (12)0.65684 (9)0.0549 (5)
O40.19464 (9)0.32143 (13)0.44743 (10)0.0569 (5)
O50.22764 (11)0.24248 (13)0.34091 (10)0.0631 (6)
O60.54745 (10)0.23529 (12)0.30214 (8)0.0518 (5)
O70.66627 (9)0.28940 (12)0.40564 (9)0.0507 (5)
N30.49861 (10)0.43835 (11)0.63197 (9)0.0379 (4)
N40.25133 (10)0.29121 (12)0.40756 (10)0.0428 (5)
C90.57563 (13)0.27360 (13)0.37128 (12)0.0398 (6)
C410.54458 (10)0.35627 (11)0.50735 (10)0.0298 (4)
C420.50987 (11)0.30564 (12)0.42622 (10)0.0314 (5)
C430.41587 (11)0.28489 (12)0.39522 (10)0.0329 (5)
H430.3950870.2499010.3423480.0394*
C440.35106 (10)0.31453 (12)0.44039 (10)0.0313 (4)
C450.37850 (10)0.36477 (12)0.51759 (10)0.0305 (4)
H450.3329010.385430.5475960.0366*
C460.47336 (11)0.38456 (11)0.55054 (9)0.0290 (4)
H70.6768410.3216830.4580630.030 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0221 (6)0.0282 (6)0.0236 (5)0.0039 (4)0.0055 (4)0.0028 (4)
N20.0209 (5)0.0268 (6)0.0227 (5)0.0035 (4)0.0063 (4)0.0032 (4)
C10.0300 (8)0.0358 (8)0.0314 (7)0.0037 (6)0.0017 (6)0.0003 (6)
C20.0301 (7)0.0308 (7)0.0334 (7)0.0076 (6)0.0033 (6)0.0004 (6)
C30.0391 (8)0.0304 (7)0.0318 (7)0.0113 (6)0.0111 (6)0.0022 (6)
C40.0216 (6)0.0331 (7)0.0302 (7)0.0026 (5)0.0075 (5)0.0076 (5)
C50.0248 (7)0.0337 (7)0.0241 (6)0.0051 (5)0.0082 (5)0.0053 (5)
C60.0232 (6)0.0304 (7)0.0265 (6)0.0032 (5)0.0088 (5)0.0047 (5)
C70.0285 (7)0.0344 (7)0.0223 (6)0.0060 (6)0.0073 (5)0.0045 (5)
C80.0197 (6)0.0247 (6)0.0245 (6)0.0003 (5)0.0054 (5)0.0010 (5)
C110.0357 (8)0.0306 (7)0.0307 (7)0.0080 (6)0.0064 (6)0.0006 (6)
C120.0398 (9)0.0415 (9)0.0337 (8)0.0067 (7)0.0042 (7)0.0007 (7)
C130.0523 (11)0.0604 (12)0.0319 (8)0.0142 (9)0.0018 (8)0.0005 (8)
C140.0691 (14)0.0629 (13)0.0354 (9)0.0230 (10)0.0149 (9)0.0159 (8)
C150.0584 (12)0.0455 (10)0.0562 (11)0.0106 (9)0.0242 (10)0.0151 (8)
C160.0392 (9)0.0350 (8)0.0444 (9)0.0049 (7)0.0090 (7)0.0039 (7)
C210.0213 (6)0.0250 (6)0.0255 (6)0.0020 (5)0.0050 (5)0.0024 (5)
C220.0311 (7)0.0329 (8)0.0325 (7)0.0030 (6)0.0114 (6)0.0046 (6)
C230.0426 (9)0.0390 (9)0.0413 (9)0.0005 (7)0.0228 (7)0.0058 (7)
C240.0344 (8)0.0391 (8)0.0493 (9)0.0028 (6)0.0245 (7)0.0078 (7)
C250.0278 (7)0.0336 (8)0.0447 (9)0.0044 (6)0.0104 (6)0.0058 (6)
C260.0269 (7)0.0271 (7)0.0323 (7)0.0015 (5)0.0079 (6)0.0002 (5)
C310.0226 (6)0.0253 (6)0.0282 (6)0.0049 (5)0.0093 (5)0.0016 (5)
C320.0327 (8)0.0296 (7)0.0367 (8)0.0017 (6)0.0076 (6)0.0021 (6)
C330.0437 (9)0.0299 (8)0.0463 (9)0.0014 (7)0.0154 (8)0.0097 (7)
C340.0452 (9)0.0381 (9)0.0313 (8)0.0104 (7)0.0109 (7)0.0090 (6)
C350.0387 (9)0.0451 (9)0.0283 (7)0.0015 (7)0.0017 (7)0.0024 (7)
C360.0316 (8)0.0337 (8)0.0310 (7)0.0020 (6)0.0073 (6)0.0020 (6)
O10.0242 (6)0.0466 (7)0.0449 (6)0.0022 (5)0.0046 (5)0.0065 (5)
O20.0364 (7)0.0954 (12)0.0457 (8)0.0021 (7)0.0029 (6)0.0243 (7)
O30.0459 (8)0.0698 (9)0.0453 (7)0.0153 (7)0.0038 (6)0.0171 (6)
O40.0239 (6)0.0732 (10)0.0713 (9)0.0049 (6)0.0067 (6)0.0008 (8)
O50.0465 (8)0.0774 (11)0.0531 (8)0.0103 (7)0.0120 (7)0.0150 (7)
O60.0595 (9)0.0612 (9)0.0400 (7)0.0066 (7)0.0226 (6)0.0026 (6)
O70.0391 (7)0.0619 (9)0.0567 (8)0.0007 (6)0.0223 (6)0.0035 (6)
N30.0355 (7)0.0405 (8)0.0347 (7)0.0038 (6)0.0023 (6)0.0023 (6)
N40.0303 (7)0.0466 (8)0.0442 (8)0.0012 (6)0.0056 (6)0.0040 (6)
C90.0393 (9)0.0352 (8)0.0491 (10)0.0046 (7)0.0190 (8)0.0095 (7)
C410.0232 (7)0.0277 (7)0.0368 (7)0.0028 (5)0.0038 (6)0.0099 (6)
C420.0330 (8)0.0293 (7)0.0345 (7)0.0049 (6)0.0133 (6)0.0074 (6)
C430.0370 (8)0.0322 (8)0.0284 (7)0.0011 (6)0.0059 (6)0.0030 (6)
C440.0238 (7)0.0334 (8)0.0333 (7)0.0012 (5)0.0000 (6)0.0037 (6)
C450.0255 (7)0.0325 (7)0.0333 (7)0.0060 (6)0.0067 (6)0.0030 (6)
C460.0282 (7)0.0282 (7)0.0282 (7)0.0018 (5)0.0017 (6)0.0016 (5)
Geometric parameters (Å, º) top
N1—H710.9448 (11)C16—H160.95
N1—C31.5141 (19)C21—C221.388 (2)
N1—C41.492 (2)C21—C261.3962 (19)
N1—C71.5036 (18)C22—H220.95
N2—C51.4718 (17)C22—C231.395 (3)
N2—C61.4682 (19)C23—H230.95
N2—C81.4848 (17)C23—C241.383 (2)
C1—H1a0.95C24—H240.95
C1—C21.317 (2)C24—C251.375 (3)
C1—C111.474 (2)C25—H250.95
C2—H20.95C25—C261.392 (2)
C2—C31.494 (2)C26—H260.95
C3—H3a0.99C31—C321.393 (2)
C3—H3b0.99C31—C361.3867 (19)
H3a—H3b1.5869C32—H320.95
C4—H4a0.99C32—C331.389 (2)
C4—H4b0.99C33—H330.95
C4—C51.511 (2)C33—C341.370 (2)
H4a—H4b1.6058C34—H340.95
C5—H5a0.99C34—C351.386 (3)
C5—H5b0.99C35—H350.95
H5a—H5b1.6091C35—C361.387 (2)
C6—H6a0.99C36—H360.95
C6—H6b0.99O1—C411.2810 (17)
C6—C71.512 (2)O2—N31.2281 (18)
H6a—H6b1.6016O3—N31.215 (2)
C7—H7a0.99O4—N41.227 (2)
C7—H7b0.99O5—N41.224 (2)
H7a—H7b1.6014O6—C91.201 (2)
C8—H81O7—C91.319 (2)
C8—C211.522 (2)O7—H70.9238 (15)
C8—C311.5282 (19)N3—C461.456 (2)
C11—C121.396 (2)N4—C441.453 (2)
C11—C161.399 (3)C9—C421.512 (3)
C12—H120.95C41—C421.444 (2)
C12—C131.390 (2)C41—C461.430 (2)
C13—H130.95C42—C431.367 (2)
C13—C141.372 (3)C43—H430.95
C14—H140.95C43—C441.379 (2)
C14—C151.382 (3)C44—C451.378 (2)
C15—H150.95C45—H450.95
C15—C161.390 (3)C45—C461.380 (2)
H71—N1—C3109.70 (10)C15—C16—H16119.61
H71—N1—C4107.37 (11)C8—C21—C22118.95 (12)
H71—N1—C7106.90 (11)C8—C21—C26122.30 (13)
C3—N1—C4112.27 (12)C22—C21—C26118.75 (14)
C3—N1—C7110.59 (11)C21—C22—H22119.72
C4—N1—C7109.82 (10)C21—C22—C23120.56 (14)
C5—N2—C6107.42 (10)H22—C22—C23119.72
C5—N2—C8110.41 (11)C22—C23—H23119.9
C6—N2—C8110.71 (11)C22—C23—C24120.20 (16)
H1a—C1—C2116.52H23—C23—C24119.9
H1a—C1—C11116.52C23—C24—H24120.2
C2—C1—C11126.96 (14)C23—C24—C25119.60 (17)
C1—C2—H2118.03H24—C24—C25120.2
C1—C2—C3123.95 (13)C24—C25—H25119.64
H2—C2—C3118.03C24—C25—C26120.72 (15)
N1—C3—C2112.26 (13)H25—C25—C26119.64
N1—C3—H3a109.47C21—C26—C25120.16 (14)
N1—C3—H3b109.47C21—C26—H26119.92
C2—C3—H3a109.47C25—C26—H26119.92
C2—C3—H3b109.47C8—C31—C32119.98 (11)
H3a—C3—H3b106.54C8—C31—C36121.61 (13)
N1—C4—H4a109.47C32—C31—C36118.41 (13)
N1—C4—H4b109.47C31—C32—H32119.64
N1—C4—C5110.53 (12)C31—C32—C33120.73 (13)
H4a—C4—H4b108.39H32—C32—C33119.64
H4a—C4—C5109.47C32—C33—H33119.85
H4b—C4—C5109.47C32—C33—C34120.30 (16)
N2—C5—C4110.21 (12)H33—C33—C34119.85
N2—C5—H5a109.47C33—C34—H34120.18
N2—C5—H5b109.47C33—C34—C35119.65 (15)
C4—C5—H5a109.47H34—C34—C35120.18
C4—C5—H5b109.47C34—C35—H35119.87
H5a—C5—H5b108.72C34—C35—C36120.25 (14)
N2—C6—H6a109.47H35—C35—C36119.88
N2—C6—H6b109.47C31—C36—C35120.65 (15)
N2—C6—C7110.93 (12)C31—C36—H36119.67
H6a—C6—H6b107.97C35—C36—H36119.68
H6a—C6—C7109.47C41—O1—H7101.64 (10)
H6b—C6—C7109.47C9—O7—H7112.68 (16)
N1—C7—C6110.95 (12)O2—N3—O3123.16 (15)
N1—C7—H7a109.47O2—N3—C46118.72 (15)
N1—C7—H7b109.47O3—N3—C46118.10 (13)
C6—C7—H7a109.47O4—N4—O5122.91 (15)
C6—C7—H7b109.47O4—N4—C44118.79 (14)
H7a—C7—H7b107.95O5—N4—C44118.29 (16)
N2—C8—H8108.39O6—C9—O7122.64 (19)
N2—C8—C21111.04 (11)O6—C9—C42122.44 (16)
N2—C8—C31110.45 (11)O7—C9—C42114.91 (15)
H8—C8—C21107.41O1—C41—C42120.00 (15)
H8—C8—C31108.03O1—C41—C46125.00 (14)
C21—C8—C31111.38 (10)C42—C41—C46115.00 (13)
C1—C11—C12122.33 (15)C9—C42—C41121.64 (14)
C1—C11—C16119.24 (13)C9—C42—C43116.80 (14)
C12—C11—C16118.42 (15)C41—C42—C43121.55 (16)
C11—C12—H12119.81C42—C43—H43119.87
C11—C12—C13120.37 (17)C42—C43—C44120.27 (14)
H12—C12—C13119.81H43—C43—C44119.87
C12—C13—H13119.82N4—C44—C43120.01 (14)
C12—C13—C14120.37 (17)N4—C44—C45118.40 (15)
H13—C13—C14119.82C43—C44—C45121.59 (13)
C13—C14—H14119.8C44—C45—H45120.57
C13—C14—C15120.40 (18)C44—C45—C46118.86 (15)
H14—C14—C15119.8H45—C45—C46120.57
C14—C15—H15120.17N3—C46—C41120.55 (13)
C14—C15—C16119.7 (2)N3—C46—C45116.73 (14)
H15—C15—C16120.17C41—C46—C45122.71 (13)
C11—C16—C15120.77 (16)O1—H7—O7148.96 (9)
C11—C16—H16119.61
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H71···O1i0.9448 (11)1.9544 (11)2.8126 (15)150.01 (8)
N1—H71···O2i0.9448 (11)2.3020 (16)3.032 (2)133.62 (8)
C3—H3a···O6ii0.992.403.340 (2)159
C5—H5a···C210.992.472.8777 (19)104
C6—H6b···C310.992.502.8974 (19)104
O7—H7···O10.9238 (15)1.6675 (13)2.505 (2)148.96 (9)
O7—H7···C410.9238 (15)2.2985 (16)2.827 (2)115.91 (9)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1/2, z+1/2.
Overview of the redetermined structures top
REFCODEChemical name original/corrected if necessary
DUJZAKaBis(quinolin-8-ol)silver(I) 2-hydroxy-3,5-dinitrobenzoate
JEVNAAbTetrakis(1H-imidazole-N3)zinc(II) bis(2-hydroxy-3,5-dinitrobenzoate / tetrakis(1H-imidazole-N3)zinc(II) bis(2-carboxy-4,6-dinitrophenolate)
LUDFULc1-Aza-8-azoniabicyclo[5.4.0]undec-7-ene 2-hydroxy-3,5-dinitrobenzoate / phenazine 2-hydroxy-3,5-dinitrobenzoic acid
NUQVEBd2-Amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate) / 2-Amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate) (0.38)/ 2-Amino-5-methylpyridinium 2-carboxy-4,6-dinitrophenolate (0.62)
QIQJADe3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium 3,5-dinitro-2-hydroxybenzoate N,N-dimethylformamide solvate / 3,5-dinitro-2-hydroxybenzoate (0.55) 2-carboxy-4,6-dinitrophenolate (0.45) N,N-dimethylformamide monosolvate / 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium 3,5-dinitro-2-hydroxybenzoate N,N-dimethylformamide monosolvate
SAFGUDfBis(1,10-phenanthroline-5,6-dione-2N,N')silver(I) 2-hydroxy-3,5-dinitrobenzoate / Bis(1,10-phenanthroline-5,6-dione-2N,N')silver(I) 2-carboxy-4,6-dinitrophenolate
SEDKETg3,5-Dimethylpyrazolium 2-carboxy-4,6-dinitrophenolate / 3,5-dimethylpyrazolium 2-hydroxy-3,5-dinitrobenzoate
TIYZIMh3-(1H-Imidazol-1-yl)propanaminium 2-carboxy-4,6-dinitrophenolate
TUJPEVi4-[(5-methylisoxazol-3-yl)aminosulfonyl]anilinium 3,5-dinitrosalicylate
VABZIJj2-Isopropyl-6-methyl-4-oxo-3,4-dihydropyrimidin-1-ium 2-carboxy-4,6-dinitrophenolatemonohydrate
WADXORk1-Aza-8-azoniabicyclo[5.4.0]undec-7-ene 2-hydroxy-3,5-dinitrobenzoate / 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium 2-hydroxy-3,5-dinitrobenzoate (0.73) / 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium 2-carboxy-4,6-2-carboxy-4,6-dinitrophenolate (0.37)
YAXPOEl4-(Diphenylmethyl)-1-(3-phenylprop-2-en-1-yl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate
Notes: (a) Zhang & Jian (2009); (b) Huang et al. (2007); (c) Senthil Kumar et al. (2002); (d) Hemamalini & Fun (2010a); (e) Sridhar et al. (2013); (f) Wang et al. (2012); (g) Wei et al. (2012); (h) Yamuna et al. (2014); (i) Malathy et al. (2015); (j) Hemamalini & Fun (2010b); (k) Smith & Lynch (2016); (l) Dayananda et al. (2012).
Hydrogen bonds (Å, °) in the redetermined structures top
The upper entries for each hydrogen bond refer to refinement Method 1: fixed hydrogen-atom positions, which were obtained from the difference electron-density maps, and refined displacement parameters. The lower entries refer to refinement Method 2: refined hydrogen-atom positions and constrained displacement parameters.
D—H···AD—HH···AD···AD—H···A
DUJZAK
O1—H1aa···O80.759 (2)1.859 (2)2.606 (3)167.96 (14)
0.97 (4)1.64 (4)2.603 (3)175 (3)
O2—H2aa···O90.922 (2)1.727 (2)2.631 (3)166.48 (15)
0.75 (4)1.90 (4)2.636 (3)165 (4)
O3—H3b···O91.040 (2)1.495 (2)2.481 (3)155.88 (12)
1.11 (4)1.41 (4)2.480 (3)160 (3)
JEVNAA
O2—H1a···O11.039 (2)1.496 (2)2.498 (2)160.4 (1)
0.89 (2)1.65 (3)2.503 (2)160 (2)
N2—H2a···O30.967 (2)1.890 (2)2.838 (3)165.9 (1)
0.84 (2)2.02 (2)2.845 (3)169 (2)
N4—H4a···O1i0.943 (2)1.924 (1)2.784 (2)150.6 (1)
0.86 (2)1.95 (2)2.792 (2)165 (2)
LUDFUL
O3—H3a···O21.059 (1)1.530 (1)2.513 (2)151.7 (1)
1.06 (2)1.51 (2)2.516 (2)156 (2)
O1—H1a···N31.163 (1)1.416 (1)2.552 (2)163.2 (1)
1.14 (2)1.44 (2)2.552 (2)166 (2)
NUQVEB
O7—H1o7···O10.919 (1)1.531 (1)2.4202 (12)161.55 (6)
1.14 (2)1.31 (2)2.4178 (12)163 (2)
O1—H1o1···O70.931 (1)1.513 (1)2.4202 (12)163.52 (6)
1.31 (2)1.14 (2)2.4178 (12)163 (2)
N2—H2a···O7ii0.892 (1)2.079 (1)2.9655 (14)172.84 (6)
0.87 (1)2.095 (14)2.9674 (14)176.5 (12)
N2—H2b···O1iii0.846 (1)2.165 (1)2.8526 (14)138.40 (6)
0.88 (2)2.146 (14)2.852 (1)137.3 (11)
N2—H2b···O2iii0.846 (1)2.413 (1)3.1741 (14)150.02 (6)
0.88 (2)2.384 (14)3.1736 (15)150.3 (11)
N1—H1···O6ii0.898 (1)1.783 (1)2.6781 (13)174.83 (6)
0.90 (1)1.784 (14)2.6773 (14)173.3 (13)
QIQJAD
N3—H3n···O20.862 (2)1.994 (2)2.854 (2)174.8 (1)
0.81 (3)2.05 (3)2.854 (3)175 (3)
N3—H4n···O8iv0.863 (2)2.059 (1)2.921 (2)176.9 (1)
0.85 (2)2.07 (2)2.920 (2)173 (3)
N2—H2n···O10.897 (2)1.831 (2)2.728 (2)177.5 (1)
0.81 (3)1.93 (3)2.731 (2)171 (2)
N5—H5n···N4v0.866 (1)2.141 (1)2.9992 (19)171.1 (1)
0.84 (2)2.17 (2)2.999 (2)171 (2)
N5—H6n···O8vi0.863 (2)2.041 (2)2.760 (2)140.2 (1)
0.78 (2)2.12 (3)2.764 (2)141 (2)
O3—H3o···O10.926 (1)1.562 (1)2.4572 (18)161.3 (1)
0.99 (3)1.49 (3)2.4569 (19)164 (3)
SAFGUD
O8—H7···O71.155 (4)1.346 (4)2.462 (6)159.6 (3)
1.05 (7)1.57 (7)2.452 (7)138 (6)
SEDKET
O1—H2a···O21.22 (5)1.34 (5)2.476 (3)149 (5)
1.27 (3)1.29 (3)2.477 (3)151 (3)
O2—H2a···O11.34 (5)1.22 (5)2.476 (3)149 (5)
1.29 (3)1.27 (3)2.477 (3)151 (3)
N1—H1···O1vii1.11 (5)1.92 (5)2.799 (4)133 (3)
0.99 (4)2.00 (3)2.804 (4)137 (3)
N1—H1···O7vii1.11 (5)1.94 (5)2.850 (4)137 (3)
0.99 (4)2.03 (3)2.855 (4)140 (3)
N2—H2···O30.96 (3)1.77 (3)2.685 (4)158 (3)
0.99 (3)1.75 (3)2.684 (4)157 (3)
TIYZIM
O2b—H2b···O1b0.982 (1)1.516 (1)2.4473 (16)156.3 (1)
1.02 (2)1.48 (2)2.4476 (16)156 (2)
N3a—H3aa···N1aaviii0.904 (1)1.932 (1)2.797 (2)159.6 (1)
0.911.922.797 (2)162
N3a—H3ab···O2bix0.901 (1)2.565 (1)3.1297 (17)121.4 (1)
0.912.583.1298 (17)120
N3a—H3ab···O2bix0.901 (1)2.565 (1)3.1297 (17)121.4 (1)
0.912.583.1297 (18)120
N3a—H3ab···O3bix0.901 (1)2.072 (1)2.9537 (17)165.8 (1)
0.912.062.9542 (17)165
N3a—H3ac···O1bx0.893 (1)2.061 (1)2.815 (2)141.5 (1)
0.912.032.815 (2)144
N3a—H3ac···O7bx0.893 (1)2.484 (1)2.9712 (19)114.7 (1)
0.912.462.9706 (19)116
TUJPEV
O6—H6a···O51.184 (1)1.295 (1)2.4268 (16)156.58 (6)
1.24 (2)1.21 (2)2.4280 (17)165.3 (14)
N1—H1a···O6xi1.002 (1)2.068 (1)3.0655 (17)173.55 (7)
0.892.243.0694 (17)155
N1—H1b···N3v0.793 (1)2.292 (1)3.0393 (15)157.3 (1)
0.892.203.0382 (15)157
N1—H1c···O4v0.832 (2)1.831 (1)2.663 (2)177.1 (1)
0.891.772.660 (2)175
N2—H2a···O50.970 (1)1.844 (1)2.7852 (15)162.64 (9)
0.827 (17)1.986 (16)2.7900 (16)164.0 (18)
VABZIJ
N3—H1n3···O6x0.973 (1)1.754 (1)2.7182 (14)170.48 (8)
0.91 (1)1.823 (14)2.7214 (14)170.8 (15)
N4—H1n4···O1w0.909 (1)1.840 (1)2.7348 (15)167.76 (8)
0.91 (2)1.833 (15)2.7323 (16)172.0 (15)
O1w—H2w1···O1xii0.917 (1)1.890 (1)2.7886 (14)166.21 (6)
0.82 (2)1.995 (19)2.7906 (15)162.7 (16)
O1w—H1w1—O3iii0.915 (1)2.040 (1)2.9352 (14)165.84 (7)
0.89 (2)2.064 (18)2.9357 (15)168.0 (17)
O7—H7···O11.019 (1)1.433 (1)2.4340 (13)165.94 (7)
0.96 (2)1.505 (16)2.4358 (13)162.0 (16)
WADXOR
N8a—H8a···O11b0.960 (2)1.933 (2)2.864 (2)162.83 (11)
0.91 (2)1.96 (2)2.869 (2)174.1 (17)
O11b—H21b···O21b1.145 (2)1.303 (6)2.433 (6)167.3 (3)
1.07 (9)1.48 (9)2.430 (6)145 (7)
O2b—H2b···O12b1.103 (2)1.385 (2)2.471 (2)166.81 (13)
0.91 (3)1.61 (3)2.475 (3)159 (3)
YAXPOE
N1—H71···O1iv0.945 (1)1.954 (1)2.813 (2)150.01 (8)
0.90 (2)1.98 (2)2.812 (2)154.0 (19)
N1—H71···O2iv0.945 (1)2.302 (2)3.032 (2)133.62 (8)
0.90 (2)2.36 (2)3.034 (2)131.8 (17)
O7—H7···O10.924 (2)1.668 (1)2.505 (2)148.96 (9)
0.92 (3)1.71 (3)2.504 (2)142 (2)
Symmetry codes: (i) -x + 3/2, -y + 1/2, -z + 1; (ii) -x + 1, -y + 1, -z; (iii) -x + 1, -y, -z; (iv) -x + 1, -y + 1, -z + 1; (v) -x + 1, -y + 2, -z + 1; (vi) x - 1, y + 1, z; (vii) -x + 1, y + 1/2, -z + 1; (viii) -x, -y, -z; (ix) x + 1, y, z; (x) -x, -y + 1, -z + 1; (xi) -x, -y + 2, -z + 1; (xii) x, y + 1, z.
Overview of selected structures with different forms of the molecules: 2-hydroxy-3,5-dinitrobenzoic acid (I); 2-hydroxy-3,5-dinitrobenzoate (II); 2-carboxy-4,6-dinitrophenolate (III); 3,5-dinitro-2-oxidobenzoate (IV) top
The structures are ordered by ascending pKα value of the base. The corresponding values of (q1 + q2), D13, D1, D2 and D5 (cf. Fig. 1) are also given.
RefcodeBase and its form present in the structurepKαΔpKαType(q1 + q2) (Å)D13 (Å)D1 (Å)D2 (Å)D5 (Å)Remarks
1GORXAMa1,4-dioxane-3.9-6.08I0.204 0.1962.547 2.5451.219 1.2201.337 1.3361.307 1.300Two independent molecules
2GORXEQa1,4-dioxane-3.9-6.08I0.2352.6011.2061.3431.319
3GORXEQ01a1,4-dioxane-3.9-6.08I0.1972.5311.2221.3461.302
4AJEBOGb4-cyanopyridinium1.92-0.26III0.0032.5231.3241.281.213
5ABULAMc2-aminoanilinium<2<-0.18III0.0112.4471.3091.2821.219
6PIDCAIc2-Aminoanilinium<2<-0.18III0.0092.441.3141.2851.229Wrongly attached hydrogen due to CO distances. Originally determined as type II but it should be III.
7PERBARd3-carbamoylpyridinium3.351.2II0.172.4521.2871.3291.239Wrongly attached hydrogen due to CO distances. Originally determined as type II but it is probably III. Disorder present in the structure.
8GIFMUEe1-naphthylammonium3.921.74III0.0112.4881.311.2791.224
9MIPROSf8-aminoquinolinium3.951.77II0.0722.4081.2781.3001.237The bridging H is situated about the centre.
10ABUKUFg4-chloroanilinium3.981.80II0.0942.4351.2761.2971.242
11YIVHIWh4-iodoanilinium4.181.63II0.1292.4611.2851.3211.228
12GIFNUFi1,10-phenanthrolinium4.272.09II0.0962.4281.2801.2971.232Determined as the type III but it is probably II (Fig. 1). The chemical name was correct.
13FOXHADj2-(pyridin-2-yl)pyridinium4.332.15II0.0472.421.3071.2921.228100 K; the reported hydrogen H3 is situated out of the plane formed by C···O bonds and is superficial.
14KEZJIJj2-(pyridin-2-yl)pyridinium4.332.15III0.072.4221.2931.2961.231CO distances are about equal. The recalculation has shown that the bridging hydrogen is about the centre of the hydrogen bond, slightly closer to atom O2, which forms a shorter CO bond.
15KEZJIJ01j2-(pyridin-2-yl)pyridinium4.332.15III0.0662.4231.2951.2991.221CO distances are about equal, the hydrogen is attached to the O atom forming a shorter CO bond.
16FICXIZkcytosinium4.602.42II0.0982.4231.2851.3101.234The type according to the CO distances should be II; the bridging hydrogen was wrongly attached.
17ABUJUElanilinium4.602.42II0.1292.4481.2801.3231.231
18ABUKOZm4-fluoroanilinium4.652.47II0.1422.4651.2731.3251.252
19GIFMOYnquinolinium4.852.67III0.052.4141.2941.2851.235The title molecule has similarly long CO distances.
20ZAJHATo2-amminobenzoic acid4.962.78II0.1352.4611.2821.3241.227
21AJEBIAppyridinium5.233.05I and II0.142 0.1632.458 2.5821.2501.3081.257Two independent molecules
22EGABOFq2-methylquinolinium5.713.53II0.2852.4111.2071.3591.244outlier
23AJECEX01r2,6-diaminopyridin-1-ium6.133.95II0.072 0.1212.435 2.4641.298 1.2951.309 1.3321.241 1.237One of the title molecules has similarly long CO distances.
24AJECIBs2-aminopyrimidinium6.824.64II0.114 0.1452.466 2.4731.277 1.2701.308 1.3231.241 1.238
25TUMWABt1H-imidazol-3-ium6.954.77III-0.012.4571.3201.2791.214
26LUMJOUuhydrazinium8.125.94III0.0142.4591.3181.2751.211
27SEDKETv3,5-dimethylpyrazolium96.82III0.0372.4811.3001.2821.224
28SEDKETv (corrected)3,5-dimethylpyrazolium96.82II0.0272.4761.3051.2771.229The bridging hydrogen after recalculation is closer to oxygen O1, which forms the shorter CO bond (C12—O1).
29LUDDETwbenzylammonium9.337.15III0.0022.4831.3051.2691.218
30LUDDET01wbenzylammonium9.337.15III1.311 1.3111.275 1.2791.217 1.219
31INELUIx1-phenylethylammonium9.797.61III0.009 0.0092.467 2.4821.309 1.3201.272 1.2771.221 1.214
32MILLOIydicyclohexylammonium10.48.22III0.0282.4641.2891.2731.225The CO distances of the title molecule are similar.
33ACIFATz4-sulfamoylanilinium10.68.42III0.0282.4621.3151.2871.209
34EGUTIJaamethylammonium10.68.42III0.0112.4811.3141.2761.218
35EGUTOPbbtriethylammonium10.788.6II0.0822.4291.2751.2861.248
36EGUTOP01bbtriethylammonium10.788.6II0.0722.4191.2751.2881.242
37FOGZILccdiethylammonium11.098.91III0.0042.4891.3081.2701.217
38XEBFAMddpiperidinium C5H11N11.289.1II and IV0.078 0.0612.586 2.7361.219 1.2341.278 1.2531.255 1.271One molecule of DNSA (I) is fully ionized, the other is in form II.
39YEJZAOeeguanidinium12.510.32II0.0792.4151.2911.3051.235
40YEJZAO01eeguanidinium12.510.32II0.0732.4151.2921.3001.239
References for the pKα values: (a) https://chemaxon.com/products/calculators-and-predictors\hashpka; (b) https://www.chemicalbook.com/ProductMSDSDetailCB0688145_EN.htm; (c) Dean (1987); (d) https://pubchem.ncbi.nlm.nih.gov/compound/nicotinamide\hashsection=pKa; (e) https://labs.chem.ucsb.edu/zhang/liming/pdf/pKas_of_Organic_Acids_and_Bases.pdf; (f) https://binarystore.wiley.com/store/10.1002/jcc.23068/asset/supinfo/JCC_23068_sm_SuppInfo.pdf?v=1&s=e864a51d58b4cdc175f6b69c92ceddb546201e3b; (g) https://sites.chem.colostate.edu/diverdi/all_courses/CRC%20reference%20data/dissociation%20constants%20of%20organic%20acids%20and%20bases.pdf; (h) https://sites.chem.colostate.edu/diverdi/all_courses/CRC%20reference%20data/dissociation%20constants%20of%20organic%20acids%20and%20bases.pdf; (i) https://chemicalland21.com/specialtychem/finechem/1,10-PHENANTHROLINE.htm; (j) https://www.chemicalbook.com/ProductMSDSDetailCB5195697_EN.htm; (k) https://www.drugfuture.com/chemdata/cytosine.html; (l) https://pubchem.ncbi.nlm.nih.gov/compound/aniline\hashsection=pKa; (m) https://sites.chem.colostate.edu/diverdi/all_courses/CRC%20reference%20data/dissociation%20constants%20of%20organic%20acids%20and%20bases.pdf; (n) Hosmane & Liebman (2009); (o) https://www.csun.edu/\~hcchm003/321/Ka.pdf; (p) https://pubchem.ncbi.nlm.nih.gov/compound/pyridine\hashsection=Dissociation-Constants; (q) https://onlinelibrary.wiley.com/doi/pdf/10.1002/jcc.23068; (r) https://www.chemicalbook.com/ProductMSDSDetailCB0236195_EN.htm; (s) https://pubchem.ncbi.nlm.nih.gov/compound/2-aminopyridine\hashsection=Dissociation-Constants; (t) https://pubchem.ncbi.nlm.nih.gov/compound/imidazole\hashsection=pKa; (u) https://evans.rc.fas.harvard.edu/pdf/evans_pKa_table.pdf; (v) https://www.chemicalbook.com/ProductMSDSDetailCB2707394_EN.htm; (w) https://pubchem.ncbi.nlm.nih.gov/compound/benzylamine\hashsection=pKa; (x) https://www.drugbank.ca/drugs/DB04325; (z) https://pubchem.ncbi.nlm.nih.gov/compound/dicyclohexylamine\hashsection=Dissociation-Constants; (z) https://pubchem.ncbi.nlm.nih.gov/compound/sulfanilamide\hashsection=Dissociation-Constants; (aa) https://pubchem.ncbi.nlm.nih.gov/compound/methylamine\hashsection=pKa; (ab) https://pubchem.ncbi.nlm.nih.gov/compound/triethylamine\hashsection=Dissociation-Constants; (ac) https://pubchem.ncbi.nlm.nih.gov/compound/diethylamine\hashsection=Dissociation-Constants; (ad) https://pubchem.ncbi.nlm.nih.gov/compound/piperidine\hashsection=Dissociation-Constants; (ae) https://pubchem.ncbi.nlm.nih.gov/compound/guanidine\hashsection=pKa.

References to publications with the chemical names of the determined compounds (original and corrected ones if necessary): (1) Senthil Kumar et al. (1999): 3,5-dinitrosalicylic acid 1,4-dioxane solvate, 3,5-dinitrosalicylic acid 1,4-dioxane (1:1)]; (2) Senthil Kumar et al. (1999): 3,5-dinitrosalicylic acid 1,4-dioxane solvate, 3,5-dinitrosalicylic acid 1,4-dioxane (2:1); (3) Senthil Kumar et al. (1999): 3,5-dinitrosalicylic acid 1,4-dioxane solvate, 3,5-dinitrosalicylic acid 1,4-dioxane (2:1); (4) Smith et al. (2003a): 4-cyanopyridinium 3,5-dinitrosalicylate, 4-cyanopyridinium 3,5-dinitrosalicylate 2-carboxy-4,6-dinitrophenolate; (5) Smith et al. (2011): 2-aminoanilinium 2-carboxy-4,6-dinitrophenolate; (6) Khan et al. (2013): 2-aminoanilinium 2-hydroxy-3,5-dinitrobenzoate, 2-aminoanilinium 2-carboxy-4,6-dinitrophenolate; (7) Jin et al. (2013): 3-carbamoylpyridinium 2-carboxy-4,6-dinitrophenolate, 3-carbamoylpyridinium 2-hydroxy-3,5-dinitrobenzoate; (8) Healy & White (2007): 1-naphthylammonium 3,5-dinitrosalicylate, 1-naphthylammonium 2-carboxy-4,6-dinitrophenolate; (9) Smith et al. (2001b): 8-aminoquinolinium 3,5-dinitrosalicylate; (10) Smith et al. (2011): 4-chloroanilinium 2-hydroxy-3,5-dinitrobenzoate; (11) Jones et al. (2014): (4-iodoanilinium 2-hydroxy-3,5-dinitrobenzoate; (12) Smith et al. (2007): 1,10-Phenanthrolinium 3,5-dinitrosalicylate; (13) Singh et al. (2014): 2-(pyridin-2-yl)pyridinium 2-hydroxy-3,5-dinitrobenzoate; (14) Song et al. (2007): 2,2'-bipyridinium 2-carboxy-4,6-dinitrophenolate; (15) Smith et al. (2007): 2,2'-bipyridinium 2-carboxy-4,6-dinitrophenolate; (16) Smith et al. (2005a): cytosinium 3,5-dinitrosalicylate, cytosinium 2-carboxy-4,6-dinitrophenolate; (17) Smith et al. (2011): anilinium 2-hydroxy-3,5-dinitrobenzoate; (18) Smith et al. (2011): 4-fluoroanilinium 2-hydroxy-3,5-dinitrobenzoate; (19) Smith, et al. (2007): quinolinium 3,5-dinitrosalicylate, quinolinium 2-carboxy-4,6-dinitrophenolate; (20) Smith et al. (1995): 3,5-dinitrosalicylic acid 2-aminobenzoic acid, 2-ammoniumbenzoic acid 2-carboxy-4,6-dinitrophenolate; (21) Smith et al. (2003b): pyridinium 3,5-dinitrosalicylate 3,5-dinitrosalicylic acid; (22) Zhang et al. (2014): 2-methylquinolinium 2-hydroxy-3,5-dinitrobenzoate; (23) Gao et al. (2015): 2,6-diaminopyridin-1-ium 2-hydroxy-3,5-dinitrobenzoate; (24) Smith et al. (2003a): 2-aminopyrimidinium 3,5-dinitrosalicylate ethanol solvate, 2-aminopyrimidinium 3,5-dinitrosalicylate ethanol (2:2:1); (25) Jin et al. (2015b): 1H-imidazol-3-ium 2-carboxy-4,6-dinitrophenolate; (26) Fu et al. (2015): hydrazinium 2-carboxy-4,6-dinitrophenolate; (27) Wei et al. (2012): (3,5-Dimethylpyrazolium 2-carboxy-4,6-dinitrophenolate); (28) this work: (3,5-dimethylpyrazolium 2-hydroxy-3,5-dinitrobenzoate; (29) Smith et al. (2002b): benzylammonium 3,5-dinitrosalicylate, benzylammonium 2-carboxy-4,6-dinitrophenolate; (30) Jin et al. (2015a): benzylammonium 2-carboxy-4,6-dinitrophenolate; (31) Smith, Wermuth & White (2003): (S)-(-)-1-phenylethylaminium 3,5-dinitrosalicylate, (S)-(-)-1-phenylethylaminium 2-carboxy-4,6-dinitrophenolate; (32) Ng et al. (2001): dicyclohexylammonium 2-carboxy-4,6-dinitrophenolate; (33) Smith et al. (2001c): 4-ammoniobenzenesulfonamide 3,5-dinitrosalicylate, 4-ammoniobenzenesulfonamide 2-carboxy-4,6-dinitrophenolate; (34) Smith et al. (2002a): methylammonium 3,5-dinitrosalicylate, methylammonium 2-carboxy-4,6-dinitrophenolate; (35) Smith et al. (2002a): triethylammonium 3,5-dinitrosalicylate; (36) Rajkumar & Chandramohan (2017): triethylammonium 2-hydroxy-3,5-dinitrobenzoate; (37) Smith et al. (2005b): diethylammonium 3,5-dinitrosalicylate, diethylammonium 2-carboxy-4,6-dinitrophenolate; (38) Smith et al. (2006): tris(piperidinium) bis(3,5-dinitrosalicylate) monohydrate, tris(piperidinium) 2-hydroxy-3,5-dinitrobenzoate 2-olate-3,5-dinitrobenzoate monohydrate; (39) Smith et al. (2001a): guanidinium 3,5-dinitrosalicylate; (40) Fu et al. (2015): guanidinium 3,5-dinitrosalicylate.
 

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