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In each asymmetric unit of the title compounds, one independent mol­ecule is present. In the crystal structure of 4-benzyl-6-phenyl-4,5-di­hydro­pyridazin-3(2H)-one, adjacent mol­ecules are linked by a pair of N—H...O hydrogen bonds, forming inversion dimers with an R_{2}^{2}(8) ring motif. The crystal structure of methyl 2-[5-(2,6-di­chloro­benz­yl)-6-oxo-3-phenyl-1,6-di­hydro-pyridazin-1-yl]acetate displays inter­molecular C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019013707/wm5515sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019013707/wm5515Isup4.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019013707/wm5515IIsup5.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019013707/wm5515Isup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019013707/wm5515IIsup5.cml
Supplementary material

CCDC references: 1958029; 1958030

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.056
  • wR factor = 0.104
  • Data-to-parameter ratio = 22.9

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low .. 41% Check PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 71.206 Check PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.306 Check PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 11.449 Check PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.098 Check PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 4.539 Check PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.808 Check
Alert level G PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size .... 0.78 mm PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 3 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 179 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 1 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 7 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 0 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 8 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Datablock: II
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections (too) Low .. 31% Check PLAT919_ALERT_3_B Reflection # Likely Affected by the Beamstop ... 1 Check PLAT920_ALERT_1_B Theta(Max) in CIF and FCF Differ by ........... 2.61 Degree PLAT921_ALERT_1_B R1 in the CIF and FCF Differ by ............... -0.0054 Check PLAT922_ALERT_1_B wR2 in the CIF and FCF Differ by ............... -0.0082 Check PLAT934_ALERT_3_B Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers .. 2 Check
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.36 Report PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00563 Ang. PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 55.170 Check PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 8.821 Check PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.651 Check PLAT923_ALERT_1_C S Values in the CIF and FCF Differ by ....... -0.142 Check PLAT928_ALERT_1_C Reported and Calculated S value Differ by . -0.112 Check
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 7 Note PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 6 Report PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT013_ALERT_1_G No _shelx_hkl_checksum Found in CIF ...... Please Check PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size .... 0.80 mm PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large 0.11 Report PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 7% Note PLAT367_ALERT_2_G Long? C(sp?)-C(sp?) Bond C18 - C19 . 1.50 Ang. PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 68 Note PLAT953_ALERT_1_G Reported (CIF) and Actual (FCF) Hmax Differ by . 2 Units PLAT954_ALERT_1_G Reported (CIF) and Actual (FCF) Kmax Differ by . 1 Units PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by . 2 Units PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ 2 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 2 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 1 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 6 ALERT level B = A potentially serious problem, consider carefully 7 ALERT level C = Check. Ensure it is not caused by an omission or oversight 15 ALERT level G = General information/check it is not something unexpected 11 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 9 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

For both structures, data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2017 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012).

4-Benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one (I) top
Crystal data top
C17H14N2OF(000) = 552
Mr = 262.30Dx = 1.252 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.819 (3) ÅCell parameters from 15196 reflections
b = 11.501 (3) Åθ = 3.2–31.3°
c = 11.187 (4) ŵ = 0.08 mm1
β = 90.93 (3)°T = 296 K
V = 1391.7 (7) Å3Prism, colourless
Z = 40.78 × 0.71 × 0.59 mm
Data collection top
STOE IPDS 2
diffractometer
4234 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1728 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.084
rotation method scansθmax = 30.9°, θmin = 3.2°
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
h = 1315
Tmin = 0.943, Tmax = 0.963k = 1616
14296 measured reflectionsl = 1516
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.034P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.88(Δ/σ)max < 0.001
4234 reflectionsΔρmax = 0.12 e Å3
185 parametersΔρmin = 0.22 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.62706 (11)0.40510 (10)0.98172 (10)0.0511 (3)
N10.48091 (14)0.45541 (13)0.84500 (12)0.0441 (4)
N20.41272 (13)0.44540 (12)0.74360 (12)0.0441 (4)
C110.44527 (16)0.36178 (14)0.67190 (15)0.0405 (4)
C20.61718 (15)0.30051 (13)0.79846 (14)0.0392 (4)
C10.57821 (16)0.38841 (14)0.88184 (15)0.0406 (4)
C100.54855 (16)0.28797 (14)0.69831 (14)0.0446 (4)
H100.5687120.2295950.6445120.053*
C30.73380 (16)0.23298 (14)0.82536 (15)0.0475 (4)
H3A0.7283340.1568340.7883630.057*
H3B0.7429720.2222040.9110460.057*
C120.37007 (16)0.34746 (15)0.56177 (15)0.0440 (4)
C40.84563 (17)0.29722 (15)0.77837 (16)0.0475 (4)
C130.33000 (17)0.23823 (18)0.52768 (17)0.0556 (5)
H130.3527470.1737420.5731150.067*
C50.9009 (2)0.38546 (17)0.84222 (19)0.0628 (5)
H50.8729350.4033990.9181910.075*
C170.33608 (18)0.44182 (17)0.49299 (16)0.0559 (5)
H170.3621990.5159990.5147750.067*
C150.22392 (19)0.3182 (2)0.35938 (19)0.0733 (6)
H150.1747050.3086620.2911530.088*
C140.25661 (19)0.2239 (2)0.4269 (2)0.0684 (6)
H140.2293890.1501090.4049940.082*
C90.8903 (2)0.2735 (2)0.66590 (19)0.0735 (6)
H90.8543880.2140960.6208050.088*
C160.2635 (2)0.4265 (2)0.39206 (18)0.0722 (6)
H160.2412510.4905230.3456960.087*
C60.9983 (2)0.4484 (2)0.7947 (3)0.0943 (9)
H61.0346280.5078830.8392570.113*
C71.0412 (3)0.4237 (3)0.6833 (4)0.1156 (12)
H71.1062220.4659520.6517150.139*
C80.9869 (3)0.3360 (3)0.6192 (3)0.1073 (10)
H81.0154100.3182690.5433880.129*
H10.4486 (16)0.5073 (16)0.9010 (16)0.060 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0612 (8)0.0586 (8)0.0334 (6)0.0067 (6)0.0021 (6)0.0081 (6)
N10.0550 (10)0.0423 (9)0.0351 (8)0.0067 (7)0.0024 (7)0.0069 (7)
N20.0504 (9)0.0452 (9)0.0366 (8)0.0039 (7)0.0012 (7)0.0033 (7)
C110.0447 (10)0.0403 (10)0.0367 (9)0.0009 (8)0.0043 (8)0.0012 (7)
C20.0466 (10)0.0351 (9)0.0360 (9)0.0009 (8)0.0024 (8)0.0002 (7)
C10.0489 (11)0.0405 (10)0.0327 (10)0.0038 (9)0.0053 (9)0.0002 (7)
C100.0539 (11)0.0399 (10)0.0399 (10)0.0019 (9)0.0004 (9)0.0092 (8)
C30.0597 (12)0.0403 (9)0.0423 (9)0.0075 (9)0.0055 (9)0.0020 (8)
C120.0397 (10)0.0539 (11)0.0384 (10)0.0057 (9)0.0028 (8)0.0086 (8)
C40.0434 (10)0.0516 (10)0.0474 (10)0.0131 (9)0.0041 (9)0.0031 (9)
C130.0514 (11)0.0595 (12)0.0556 (11)0.0084 (10)0.0070 (10)0.0142 (10)
C50.0614 (13)0.0666 (13)0.0601 (13)0.0035 (11)0.0142 (11)0.0065 (10)
C170.0572 (13)0.0602 (12)0.0501 (11)0.0030 (10)0.0025 (10)0.0021 (10)
C150.0566 (14)0.113 (2)0.0494 (12)0.0119 (14)0.0123 (10)0.0194 (14)
C140.0531 (13)0.0787 (15)0.0731 (14)0.0052 (11)0.0094 (11)0.0305 (13)
C90.0715 (15)0.0874 (16)0.0619 (13)0.0268 (13)0.0118 (12)0.0014 (12)
C160.0694 (15)0.0965 (18)0.0504 (12)0.0146 (13)0.0086 (12)0.0098 (12)
C60.0636 (16)0.097 (2)0.121 (2)0.0194 (15)0.0214 (17)0.0302 (18)
C70.0527 (17)0.144 (3)0.151 (3)0.0057 (18)0.0204 (19)0.063 (3)
C80.077 (2)0.149 (3)0.096 (2)0.036 (2)0.0412 (17)0.022 (2)
Geometric parameters (Å, º) top
O1—C11.243 (2)C13—C141.378 (3)
N1—N21.348 (2)C13—H130.9300
N1—C11.363 (2)C5—C61.390 (3)
N1—H10.937 (18)C5—H50.9300
N2—C111.3044 (19)C17—C161.376 (3)
C11—C101.430 (2)C17—H170.9300
C11—C121.475 (2)C15—C141.365 (3)
C2—C101.342 (2)C15—C161.365 (3)
C2—C11.443 (2)C15—H150.9300
C2—C31.508 (2)C14—H140.9300
C10—H100.9300C9—C81.379 (4)
C3—C41.519 (2)C9—H90.9300
C3—H3A0.9700C16—H160.9300
C3—H3B0.9700C6—C71.367 (4)
C12—C171.377 (2)C6—H60.9300
C12—C131.381 (2)C7—C81.364 (4)
C4—C51.373 (3)C7—H70.9300
C4—C91.382 (3)C8—H80.9300
N2—N1—C1128.00 (14)C14—C13—H13119.7
N2—N1—H1114.4 (11)C12—C13—H13119.7
C1—N1—H1116.9 (11)C4—C5—C6120.8 (2)
C11—N2—N1115.52 (15)C4—C5—H5119.6
N2—C11—C10121.89 (16)C6—C5—H5119.6
N2—C11—C12116.44 (15)C16—C17—C12120.1 (2)
C10—C11—C12121.67 (15)C16—C17—H17120.0
C10—C2—C1116.83 (16)C12—C17—H17120.0
C10—C2—C3124.15 (15)C14—C15—C16120.0 (2)
C1—C2—C3118.96 (15)C14—C15—H15120.0
O1—C1—N1119.96 (15)C16—C15—H15120.0
O1—C1—C2124.38 (17)C15—C14—C13119.9 (2)
N1—C1—C2115.66 (15)C15—C14—H14120.1
C2—C10—C11121.92 (15)C13—C14—H14120.1
C2—C10—H10119.0C8—C9—C4121.3 (2)
C11—C10—H10119.0C8—C9—H9119.3
C2—C3—C4110.44 (14)C4—C9—H9119.3
C2—C3—H3A109.6C15—C16—C17120.6 (2)
C4—C3—H3A109.6C15—C16—H16119.7
C2—C3—H3B109.6C17—C16—H16119.7
C4—C3—H3B109.6C7—C6—C5120.7 (3)
H3A—C3—H3B108.1C7—C6—H6119.6
C17—C12—C13118.88 (17)C5—C6—H6119.6
C17—C12—C11121.17 (16)C8—C7—C6118.9 (3)
C13—C12—C11119.93 (17)C8—C7—H7120.5
C5—C4—C9117.6 (2)C6—C7—H7120.5
C5—C4—C3121.50 (17)C7—C8—C9120.6 (3)
C9—C4—C3120.73 (19)C7—C8—H8119.7
C14—C13—C12120.6 (2)C9—C8—H8119.7
C1—N1—N2—C110.7 (2)C2—C3—C4—C582.6 (2)
N1—N2—C11—C101.6 (2)C2—C3—C4—C993.2 (2)
N1—N2—C11—C12178.58 (15)C17—C12—C13—C140.4 (3)
N2—N1—C1—O1175.85 (16)C11—C12—C13—C14178.07 (17)
N2—N1—C1—C24.0 (2)C9—C4—C5—C60.1 (3)
C10—C2—C1—O1174.96 (17)C3—C4—C5—C6175.88 (18)
C3—C2—C1—O17.8 (2)C13—C12—C17—C160.1 (3)
C10—C2—C1—N14.9 (2)C11—C12—C17—C16178.52 (17)
C3—C2—C1—N1172.33 (14)C16—C15—C14—C130.3 (3)
C1—C2—C10—C113.1 (2)C12—C13—C14—C150.6 (3)
C3—C2—C10—C11173.96 (15)C5—C4—C9—C80.0 (3)
N2—C11—C10—C20.3 (3)C3—C4—C9—C8176.0 (2)
C12—C11—C10—C2179.90 (16)C14—C15—C16—C170.2 (3)
C10—C2—C3—C490.0 (2)C12—C17—C16—C150.4 (3)
C1—C2—C3—C486.97 (18)C4—C5—C6—C70.0 (4)
N2—C11—C12—C1745.2 (2)C5—C6—C7—C80.1 (4)
C10—C11—C12—C17134.69 (17)C6—C7—C8—C90.1 (4)
N2—C11—C12—C13133.26 (17)C4—C9—C8—C70.1 (4)
C10—C11—C12—C1346.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O1i0.932.483.404 (2)172
N1—H1···O1ii0.937 (18)1.855 (19)2.7873 (19)173.0 (16)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y+1, z+2.
Methyl 2-[5-(2,6-dichlorobenzyl)-6-oxo-3-phenyl-1,4,5,6-tetrahydro-pyridazin-1-yl]acetate (II) top
Crystal data top
C20H16Cl2N2O3F(000) = 832
Mr = 403.25Dx = 1.359 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.2730 (13) ÅCell parameters from 14081 reflections
b = 12.3808 (9) Åθ = 1.6–30.5°
c = 14.1405 (15) ŵ = 0.35 mm1
β = 92.801 (9)°T = 296 K
V = 1971.2 (3) Å3Cubic, colourless
Z = 40.80 × 0.76 × 0.60 mm
Data collection top
STOE IPDS 2
diffractometer
6015 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1892 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.095
rotation method scansθmax = 30.6°, θmin = 1.8°
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
h = 1416
Tmin = 0.762, Tmax = 0.832k = 1717
19293 measured reflectionsl = 2020
Refinement top
Refinement on F268 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.231 w = 1/[σ2(Fo2) + (0.1133P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.83(Δ/σ)max < 0.001
6015 reflectionsΔρmax = 0.96 e Å3
265 parametersΔρmin = 0.28 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl20.28302 (11)0.78380 (8)0.39545 (9)0.0874 (4)
Cl10.11530 (12)0.56182 (11)0.68990 (9)0.0990 (4)
O10.4761 (2)0.6024 (2)0.73816 (19)0.0734 (8)
O20.7312 (3)0.4765 (2)0.6889 (2)0.0785 (8)
N20.4886 (3)0.4295 (2)0.6878 (2)0.0598 (8)
N10.4620 (3)0.3458 (2)0.6290 (2)0.0589 (8)
C100.3921 (3)0.3643 (2)0.5550 (2)0.0521 (8)
C90.3431 (3)0.4694 (2)0.5375 (3)0.0525 (8)
H90.2939910.4807180.4836170.063*
C80.3664 (3)0.5517 (2)0.5968 (2)0.0522 (8)
C60.1935 (3)0.6695 (3)0.5385 (3)0.0575 (9)
C170.4456 (3)0.5342 (3)0.6787 (3)0.0570 (9)
C110.3627 (3)0.2690 (3)0.4945 (3)0.0555 (9)
C50.1694 (3)0.7216 (3)0.4534 (3)0.0645 (10)
C70.3150 (3)0.6633 (3)0.5872 (3)0.0624 (10)
H7A0.3688060.7075340.5522540.075*
H7B0.3110270.6943490.6499530.075*
C190.6926 (4)0.4357 (3)0.7570 (3)0.0660 (9)
C120.3198 (3)0.2793 (3)0.4022 (3)0.0636 (10)
H120.3119700.3478920.3757770.076*
C180.5661 (3)0.4012 (3)0.7686 (3)0.0659 (10)
H18A0.5638810.3236460.7778730.079*
H18B0.5370300.4351490.8248350.079*
C10.0960 (4)0.6252 (3)0.5811 (3)0.0689 (10)
C160.3768 (4)0.1655 (3)0.5324 (3)0.0702 (11)
H160.4064430.1563630.5944230.084*
C130.2881 (4)0.1900 (3)0.3477 (3)0.0761 (12)
H130.2581830.1990130.2857670.091*
C140.3009 (4)0.0890 (3)0.3850 (3)0.0779 (12)
H140.2791120.0288040.3488340.093*
C150.3463 (4)0.0763 (3)0.4771 (3)0.0832 (13)
H150.3565130.0072580.5020850.100*
C40.0557 (4)0.7290 (4)0.4124 (4)0.0859 (13)
H40.0426960.7651850.3552040.103*
C20.0182 (4)0.6326 (4)0.5418 (4)0.0892 (14)
H20.0816670.6036910.5729540.107*
C30.0371 (4)0.6835 (4)0.4557 (4)0.0965 (16)
H30.1131400.6866650.4272090.116*
O3A0.7602 (3)0.3969 (6)0.8303 (3)0.0728 (15)0.626 (11)
C20A0.8977 (5)0.4168 (8)0.8327 (6)0.092 (2)0.626 (11)
H20A0.9188460.4493460.7742250.138*0.626 (11)
H20B0.9385590.3492100.8410050.138*0.626 (11)
H20C0.9199350.4641470.8843680.138*0.626 (11)
O3B0.7492 (6)0.4387 (10)0.8431 (4)0.0755 (19)0.374 (11)
C20B0.8759 (9)0.4925 (14)0.8535 (8)0.091 (3)0.374 (11)
H20D0.9167040.4820910.7962410.137*0.374 (11)
H20E0.9206060.4598310.9054870.137*0.374 (11)
H20F0.8674050.5684350.8652760.137*0.374 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl20.1012 (9)0.0618 (6)0.0996 (9)0.0013 (6)0.0092 (7)0.0122 (6)
Cl10.1100 (10)0.1085 (9)0.0791 (8)0.0063 (7)0.0106 (7)0.0075 (7)
O10.0876 (19)0.0628 (15)0.0671 (17)0.0012 (13)0.0224 (14)0.0133 (13)
O20.0850 (19)0.0732 (17)0.0761 (17)0.0032 (14)0.0089 (15)0.0184 (15)
N20.0670 (19)0.0536 (17)0.0570 (17)0.0014 (14)0.0160 (15)0.0007 (15)
N10.0655 (19)0.0484 (16)0.0619 (18)0.0012 (14)0.0076 (15)0.0044 (15)
C100.0540 (19)0.0444 (17)0.057 (2)0.0001 (14)0.0094 (16)0.0043 (16)
C90.0537 (19)0.0460 (17)0.056 (2)0.0014 (14)0.0114 (16)0.0009 (15)
C80.0517 (19)0.0446 (17)0.059 (2)0.0005 (14)0.0086 (15)0.0009 (15)
C60.061 (2)0.0389 (17)0.071 (2)0.0010 (15)0.0111 (18)0.0091 (17)
C170.060 (2)0.0491 (19)0.061 (2)0.0023 (16)0.0075 (17)0.0020 (17)
C110.060 (2)0.0422 (18)0.064 (2)0.0032 (15)0.0006 (17)0.0027 (16)
C50.070 (2)0.0454 (18)0.078 (3)0.0046 (17)0.000 (2)0.0051 (18)
C70.063 (2)0.0433 (18)0.079 (3)0.0013 (16)0.0172 (19)0.0063 (18)
C190.079 (2)0.0544 (19)0.062 (2)0.0015 (17)0.0175 (17)0.0069 (17)
C120.079 (2)0.0496 (19)0.062 (2)0.0016 (18)0.0031 (19)0.0021 (17)
C180.067 (2)0.068 (2)0.061 (2)0.0009 (19)0.0169 (19)0.0138 (19)
C10.068 (3)0.059 (2)0.079 (3)0.0023 (18)0.005 (2)0.0094 (19)
C160.093 (3)0.048 (2)0.068 (2)0.0014 (19)0.012 (2)0.0026 (19)
C130.097 (3)0.066 (3)0.064 (2)0.004 (2)0.005 (2)0.013 (2)
C140.097 (3)0.054 (2)0.082 (3)0.003 (2)0.001 (2)0.017 (2)
C150.115 (4)0.044 (2)0.090 (3)0.003 (2)0.001 (3)0.004 (2)
C40.087 (3)0.079 (3)0.089 (3)0.017 (2)0.022 (3)0.004 (2)
C20.063 (3)0.093 (3)0.111 (4)0.000 (2)0.000 (3)0.010 (3)
C30.060 (3)0.105 (4)0.122 (4)0.011 (3)0.025 (3)0.009 (3)
O3A0.075 (2)0.068 (3)0.072 (2)0.011 (2)0.025 (2)0.011 (2)
C20A0.087 (3)0.083 (5)0.105 (5)0.025 (4)0.008 (4)0.018 (4)
O3B0.080 (3)0.074 (4)0.070 (3)0.009 (3)0.023 (3)0.005 (3)
C20B0.072 (5)0.102 (6)0.100 (6)0.003 (5)0.001 (4)0.024 (6)
Geometric parameters (Å, º) top
Cl2—C51.734 (4)C12—C131.384 (5)
Cl1—C11.731 (4)C12—H120.9300
O1—C171.228 (4)C18—H18A0.9700
O2—C191.189 (5)C18—H18B0.9700
N2—N11.353 (4)C1—C21.380 (6)
N2—C171.388 (4)C16—C151.387 (5)
N2—C181.447 (4)C16—H160.9300
N1—C101.299 (4)C13—C141.363 (6)
C10—C91.430 (4)C13—H130.9300
C10—C111.484 (4)C14—C151.384 (6)
C9—C81.338 (4)C14—H140.9300
C9—H90.9300C15—H150.9300
C8—C171.444 (5)C4—C31.359 (7)
C8—C71.503 (4)C4—H40.9300
C6—C51.381 (5)C2—C31.378 (7)
C6—C11.392 (6)C2—H20.9300
C6—C71.504 (5)C3—H30.9300
C11—C121.376 (5)O3A—C20A1.569 (6)
C11—C161.395 (5)C20A—H20A0.9600
C5—C41.384 (6)C20A—H20B0.9600
C7—H7A0.9700C20A—H20C0.9600
C7—H7B0.9700O3B—C20B1.576 (7)
C19—O3A1.344 (5)C20B—H20D0.9600
C19—O3B1.347 (5)C20B—H20E0.9600
C19—C181.505 (6)C20B—H20F0.9600
N1—N2—C17126.3 (3)N2—C18—H18B109.1
N1—N2—C18114.1 (3)C19—C18—H18B109.1
C17—N2—C18119.6 (3)H18A—C18—H18B107.8
C10—N1—N2117.9 (3)C2—C1—C6122.7 (4)
N1—C10—C9120.9 (3)C2—C1—Cl1117.6 (4)
N1—C10—C11115.7 (3)C6—C1—Cl1119.7 (3)
C9—C10—C11123.3 (3)C15—C16—C11119.6 (4)
C8—C9—C10121.5 (3)C15—C16—H16120.2
C8—C9—H9119.3C11—C16—H16120.2
C10—C9—H9119.3C14—C13—C12119.9 (4)
C9—C8—C17118.9 (3)C14—C13—H13120.1
C9—C8—C7125.6 (3)C12—C13—H13120.1
C17—C8—C7115.5 (3)C13—C14—C15119.7 (4)
C5—C6—C1115.8 (3)C13—C14—H14120.2
C5—C6—C7123.9 (4)C15—C14—H14120.2
C1—C6—C7120.2 (3)C14—C15—C16120.7 (4)
O1—C17—N2119.6 (3)C14—C15—H15119.7
O1—C17—C8126.0 (3)C16—C15—H15119.7
N2—C17—C8114.4 (3)C3—C4—C5120.1 (4)
C12—C11—C16118.5 (3)C3—C4—H4120.0
C12—C11—C10122.1 (3)C5—C4—H4120.0
C16—C11—C10119.4 (3)C3—C2—C1119.2 (5)
C6—C5—C4122.3 (4)C3—C2—H2120.4
C6—C5—Cl2120.1 (3)C1—C2—H2120.4
C4—C5—Cl2117.6 (4)C4—C3—C2119.9 (4)
C8—C7—C6115.2 (3)C4—C3—H3120.1
C8—C7—H7A108.5C2—C3—H3120.1
C6—C7—H7A108.5C19—O3A—C20A118.9 (4)
C8—C7—H7B108.5O3A—C20A—H20A109.5
C6—C7—H7B108.5O3A—C20A—H20B109.5
H7A—C7—H7B107.5H20A—C20A—H20B109.5
O2—C19—O3A124.0 (4)O3A—C20A—H20C109.5
O2—C19—O3B123.0 (4)H20A—C20A—H20C109.5
O2—C19—C18126.5 (3)H20B—C20A—H20C109.5
O3A—C19—C18108.6 (4)C19—O3B—C20B118.9 (5)
O3B—C19—C18108.6 (4)O3B—C20B—H20D109.5
C11—C12—C13121.6 (3)O3B—C20B—H20E109.5
C11—C12—H12119.2H20D—C20B—H20E109.5
C13—C12—H12119.2O3B—C20B—H20F109.5
N2—C18—C19112.6 (3)H20D—C20B—H20F109.5
N2—C18—H18A109.1H20E—C20B—H20F109.5
C19—C18—H18A109.1
C17—N2—N1—C101.9 (5)C16—C11—C12—C131.6 (6)
C18—N2—N1—C10179.5 (3)C10—C11—C12—C13177.3 (4)
N2—N1—C10—C91.2 (5)N1—N2—C18—C19102.0 (4)
N2—N1—C10—C11178.0 (3)C17—N2—C18—C1980.2 (4)
N1—C10—C9—C80.7 (6)O2—C19—C18—N24.0 (6)
C11—C10—C9—C8176.0 (3)O3A—C19—C18—N2173.8 (4)
C10—C9—C8—C171.8 (5)O3B—C19—C18—N2160.7 (6)
C10—C9—C8—C7176.9 (4)C5—C6—C1—C20.2 (6)
N1—N2—C17—O1179.1 (3)C7—C6—C1—C2177.1 (4)
C18—N2—C17—O11.7 (5)C5—C6—C1—Cl1177.9 (3)
N1—N2—C17—C80.8 (5)C7—C6—C1—Cl10.6 (5)
C18—N2—C17—C8178.2 (3)C12—C11—C16—C150.7 (6)
C9—C8—C17—O1179.0 (4)C10—C11—C16—C15178.2 (4)
C7—C8—C17—O12.1 (6)C11—C12—C13—C141.0 (7)
C9—C8—C17—N21.1 (5)C12—C13—C14—C150.5 (7)
C7—C8—C17—N2177.8 (3)C13—C14—C15—C161.3 (7)
N1—C10—C11—C12160.9 (3)C11—C16—C15—C140.7 (7)
C9—C10—C11—C1222.3 (6)C6—C5—C4—C30.4 (7)
N1—C10—C11—C1620.2 (5)Cl2—C5—C4—C3178.8 (4)
C9—C10—C11—C16156.6 (4)C6—C1—C2—C31.7 (7)
C1—C6—C5—C40.4 (5)Cl1—C1—C2—C3179.4 (4)
C7—C6—C5—C4177.6 (4)C5—C4—C3—C21.9 (7)
C1—C6—C5—Cl2178.0 (3)C1—C2—C3—C42.5 (7)
C7—C6—C5—Cl20.8 (5)O2—C19—O3A—C20A6.9 (8)
C9—C8—C7—C629.2 (6)C18—C19—O3A—C20A177.1 (5)
C17—C8—C7—C6149.6 (3)O2—C19—O3B—C20B3.6 (13)
C5—C6—C7—C8116.0 (4)C18—C19—O3B—C20B168.9 (8)
C1—C6—C7—C866.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O2i0.932.503.337 (4)150
C12—H12···O2i0.932.403.326 (4)174
Symmetry code: (i) x+1, y+1, z+1.
 

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