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A few pyrazinamide (Pyz) cocrystals involving hy­droxy­benzoic/cinnamic acid derivatives [2,4-di­hydroxy­benzoic acid (24DHBA); 2,6-di­hydroxy­benzoic acid (26DHBA); 3,5-di­hydroxy­benzoic acid (35DHBA) and nutraceutical molecule ferulic acid (FRA)] and the first example of a molecular salt with p-toluene­sulfonic acid (pTSA) have been prepared and characterized using various solid-state techniques. A high-temperature cocrystal polymorph of Pyz·FRA has been characterized from the endothermic peaks observed using differential scanning calorimetry. The presence of substituent groups carrying hydrogen bond donors or acceptors and their influence on supramolecular synthon formation has been investigated using a Cambridge Structural Database search. Equilibrium solubility of all the binary complexes of Pyz follows the order of their coformer solubility, i.e. Pyz+·pTSA > Pyz·35DHBA > Pyz > Pyz·26DHBA > Pyz·24DHBA > Pyz·FRA. A twofold enhancement in solubility of Pyz+·pTSA molecular salt compared with the parent drug suggests a potential drug formulation for the treatment of tuberculosis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520617011477/rm5006sup1.cif
Contains datablocks PYZ_24DHBA, PYZ_26DHBA, Pyz_35DHBA, Pyz-Ferulic_acid, PYZ_pTSA

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617011477/rm5006PYZ_24DHBAsup2.hkl
PYZ_24DHBA hkl

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617011477/rm5006PYZ_26DHBAsup3.hkl
PYZ_26DHBA hkl

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617011477/rm5006Pyz_35DHBAsup4.hkl
Pyz_35DHBA hkl

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617011477/rm5006Pyz_Ferulic_acidsup5.hkl
PYZ_Ferulic acid hkl

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617011477/rm5006PYZ_pTSAsup6.hkl
PYZ_pTSA hkl

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520617011477/rm5006sup7.pdf
Experimental section; Tables S1 to S3; Figs. S1 to S9

CCDC references: 1504475; 1504478; 1504476; 1504479; 1504477; 1504479

Computing details top

For all structures, data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXL2016/6 (Sheldrick, 2016); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2016); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.

(PYZ_24DHBA) top
Crystal data top
C7H6O4·C5H5N3OF(000) = 576
Mr = 277.24Dx = 1.470 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.7759 (8) ÅCell parameters from 3570 reflections
b = 6.7421 (6) Åθ = 2.6–26.1°
c = 23.996 (2) ŵ = 0.12 mm1
β = 95.224 (6)°T = 296 K
V = 1252.8 (2) Å3Block, colorless
Z = 40.27 × 0.18 × 0.16 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2124 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
φ and ω scansθmax = 26.5°, θmin = 2.6°
Absorption correction: multi-scan
Bruker AXS SADABS program
h = 99
Tmin = 0.969, Tmax = 0.982k = 87
9812 measured reflectionsl = 3030
2564 independent reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.044 w = 1/[σ2(Fo2) + (0.0756P)2 + 0.1634P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.125(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.33 e Å3
2564 reflectionsΔρmin = 0.28 e Å3
202 parametersExtinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.066 (6)
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
C10.18875 (18)0.6795 (2)0.09166 (5)0.0370 (3)
C20.2703 (2)0.7256 (2)0.14391 (6)0.0418 (4)
H20.3301790.8446740.1488270.050*
C30.1781 (2)0.4343 (3)0.17754 (6)0.0476 (4)
H30.1712310.3450030.2067880.057*
C40.0980 (2)0.3883 (2)0.12528 (6)0.0456 (4)
H40.0394950.2684120.1203690.055*
C50.1983 (2)0.8224 (2)0.04435 (6)0.0421 (4)
C60.68469 (18)0.6105 (2)0.10862 (6)0.0369 (3)
C70.74549 (18)0.6081 (2)0.16564 (6)0.0387 (4)
C80.7081 (2)0.4494 (2)0.19922 (6)0.0427 (4)
H80.7489900.4483440.2368610.051*
C90.60961 (19)0.2920 (2)0.17678 (6)0.0409 (4)
C100.5481 (2)0.2927 (2)0.12037 (6)0.0431 (4)
H100.4821970.1873960.1052330.052*
C110.58545 (19)0.4495 (2)0.08754 (6)0.0412 (4)
H110.5436270.4492880.0499770.049*
C120.7288 (2)0.7731 (2)0.07251 (6)0.0425 (4)
H2A0.692 (3)0.856 (4)0.0020 (11)0.099 (8)*
H3A0.082 (3)0.646 (3)0.0107 (8)0.062 (6)*
H4A0.854 (3)0.855 (4)0.1618 (10)0.079 (7)*
H5A0.620 (3)0.135 (3)0.2413 (10)0.072 (6)*
H3B0.138 (3)0.848 (3)0.0342 (10)0.071 (6)*
N10.26447 (17)0.6029 (2)0.18705 (5)0.0450 (3)
N20.10226 (16)0.51007 (19)0.08191 (5)0.0399 (3)
N30.1311 (2)0.7680 (2)0.00544 (6)0.0537 (4)
O10.2658 (2)0.98595 (19)0.05387 (5)0.0690 (4)
O20.66837 (19)0.7519 (2)0.01996 (5)0.0688 (4)
O30.81772 (15)0.91669 (17)0.08891 (4)0.0512 (3)
O40.84357 (16)0.75641 (19)0.18942 (5)0.0550 (4)
O50.56468 (18)0.1350 (2)0.20717 (5)0.0602 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0395 (7)0.0393 (8)0.0315 (7)0.0015 (6)0.0002 (5)0.0017 (6)
C20.0479 (8)0.0425 (9)0.0340 (7)0.0030 (7)0.0028 (6)0.0034 (6)
C30.0595 (10)0.0489 (10)0.0337 (7)0.0036 (8)0.0003 (6)0.0056 (6)
C40.0535 (9)0.0415 (9)0.0409 (8)0.0056 (7)0.0008 (6)0.0032 (6)
C50.0489 (8)0.0431 (9)0.0332 (7)0.0107 (7)0.0029 (6)0.0007 (6)
C60.0360 (7)0.0426 (9)0.0319 (7)0.0003 (6)0.0011 (5)0.0001 (6)
C70.0389 (7)0.0445 (9)0.0320 (7)0.0003 (6)0.0006 (5)0.0068 (6)
C80.0470 (8)0.0533 (10)0.0264 (6)0.0010 (7)0.0040 (5)0.0011 (6)
C90.0452 (8)0.0441 (9)0.0330 (7)0.0000 (7)0.0007 (6)0.0044 (6)
C100.0487 (8)0.0456 (9)0.0334 (7)0.0077 (7)0.0047 (6)0.0006 (6)
C110.0459 (8)0.0487 (9)0.0277 (6)0.0031 (7)0.0039 (5)0.0009 (6)
C120.0464 (8)0.0464 (9)0.0339 (7)0.0036 (7)0.0000 (6)0.0009 (6)
N10.0529 (7)0.0503 (8)0.0303 (6)0.0038 (6)0.0048 (5)0.0019 (5)
N20.0455 (7)0.0389 (7)0.0344 (6)0.0054 (6)0.0020 (5)0.0003 (5)
N30.0806 (10)0.0487 (9)0.0300 (7)0.0244 (8)0.0047 (6)0.0014 (6)
O10.1066 (11)0.0561 (8)0.0398 (6)0.0391 (8)0.0182 (6)0.0070 (5)
O20.0998 (11)0.0680 (9)0.0347 (6)0.0382 (8)0.0143 (6)0.0128 (6)
O30.0651 (7)0.0467 (7)0.0405 (6)0.0129 (6)0.0017 (5)0.0015 (5)
O40.0712 (8)0.0530 (8)0.0385 (6)0.0161 (6)0.0078 (5)0.0054 (5)
O50.0800 (9)0.0591 (8)0.0385 (6)0.0186 (7)0.0116 (6)0.0136 (5)
Geometric parameters (Å, º) top
C1—N21.3353 (19)C7—C81.386 (2)
C1—C21.3878 (19)C8—C91.388 (2)
C1—C51.496 (2)C8—H80.9300
C2—N11.329 (2)C9—O51.3488 (19)
C2—H20.9300C9—C101.3941 (19)
C3—N11.329 (2)C10—C111.365 (2)
C3—C41.383 (2)C10—H100.9300
C3—H30.9300C11—H110.9300
C4—N21.3283 (19)C12—O31.2331 (19)
C4—H40.9300C12—O21.3126 (18)
C5—O11.2337 (19)N3—H3A0.91 (2)
C5—N31.3120 (19)N3—H3B0.88 (2)
C6—C111.399 (2)O2—H2A0.91 (3)
C6—C71.4064 (18)O4—H4A0.95 (3)
C6—C121.458 (2)O5—H5A0.89 (2)
C7—O41.3522 (18)
N2—C1—C2122.10 (13)C7—C8—H8119.9
N2—C1—C5118.49 (12)C9—C8—H8119.9
C2—C1—C5119.41 (13)O5—C9—C8123.43 (13)
N1—C2—C1121.25 (14)O5—C9—C10116.42 (14)
N1—C2—H2119.4C8—C9—C10120.13 (13)
C1—C2—H2119.4C11—C10—C9119.41 (14)
N1—C3—C4121.73 (14)C11—C10—H10120.3
N1—C3—H3119.1C9—C10—H10120.3
C4—C3—H3119.1C10—C11—C6122.09 (12)
N2—C4—C3122.04 (15)C10—C11—H11119.0
N2—C4—H4119.0C6—C11—H11119.0
C3—C4—H4119.0O3—C12—O2122.22 (14)
O1—C5—N3123.08 (15)O3—C12—C6123.80 (13)
O1—C5—C1119.01 (12)O2—C12—C6113.97 (14)
N3—C5—C1117.90 (14)C2—N1—C3116.81 (12)
C11—C6—C7117.91 (13)C4—N2—C1116.06 (12)
C11—C6—C12121.36 (12)C5—N3—H3A120.4 (12)
C7—C6—C12120.70 (13)C5—N3—H3B119.7 (14)
O4—C7—C8117.76 (12)H3A—N3—H3B119.9 (19)
O4—C7—C6121.92 (14)C12—O2—H2A113.7 (17)
C8—C7—C6120.31 (13)C7—O4—H4A107.9 (14)
C7—C8—C9120.15 (12)C9—O5—H5A111.5 (15)
(PYZ_26DHBA) top
Crystal data top
C7H6O4·C5H5N3OF(000) = 576
Mr = 277.24Dx = 1.558 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.0839 (15) ÅCell parameters from 4900 reflections
b = 5.0936 (8) Åθ = 2.5–25.8°
c = 23.335 (3) ŵ = 0.12 mm1
β = 99.605 (8)°T = 293 K
V = 1181.8 (3) Å3Needle, yellow
Z = 40.90 × 0.21 × 0.08 mm
Data collection top
Bruker APEX-II CCD
diffractometer
1827 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.075
φ and ω scansθmax = 26.5°, θmin = 2.5°
Absorption correction: multi-scan
Bruker AXS SADABS program
h = 1212
Tmin = 0.897, Tmax = 0.990k = 66
16225 measured reflectionsl = 2925
2413 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.137 w = 1/[σ2(Fo2) + (0.0771P)2 + 0.1214P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
2413 reflectionsΔρmax = 0.20 e Å3
181 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*/Ueq
O30.13875 (14)0.7030 (3)0.46846 (5)0.0475 (4)
O20.30423 (13)0.8732 (3)0.42840 (5)0.0449 (4)
H2A0.3168981.0209950.4639370.067*
O40.00526 (14)0.3121 (3)0.42031 (6)0.0536 (4)
H4A0.0364980.4407540.4486810.080*
O50.34566 (12)0.7251 (2)0.32621 (5)0.0412 (3)
H5A0.3552160.8233170.3602850.062*
C60.17650 (16)0.5352 (3)0.37772 (6)0.0324 (4)
C70.07447 (17)0.3420 (3)0.37611 (7)0.0367 (4)
C80.04381 (19)0.1764 (4)0.32889 (8)0.0431 (4)
H80.0237030.0513560.3279560.052*
C90.11341 (19)0.1974 (4)0.28337 (8)0.0425 (4)
H90.0924380.0853570.2516900.051*
C100.21406 (18)0.3816 (4)0.28365 (7)0.0396 (4)
H100.2604540.3918540.2524630.047*
C110.24579 (17)0.5503 (3)0.33011 (7)0.0335 (4)
C120.20399 (17)0.7087 (3)0.42845 (7)0.0343 (4)
O10.34994 (13)0.2781 (3)0.00680 (5)0.0463 (4)
N10.48221 (16)0.3132 (3)0.12588 (6)0.0422 (4)
N20.29239 (16)0.0639 (3)0.14428 (6)0.0423 (4)
N30.18861 (16)0.3917 (3)0.05846 (7)0.0474 (4)
H3A0.1557020.3605690.0905640.057*
H3B0.1520920.5143990.0318240.057*
C10.34313 (17)0.0529 (3)0.09513 (7)0.0337 (4)
C20.43729 (18)0.1328 (3)0.08613 (7)0.0377 (4)
H20.4703050.1316410.0512220.045*
C30.4328 (2)0.3009 (4)0.17479 (8)0.0435 (5)
H30.4619190.4225020.2039050.052*
C40.3394 (2)0.1136 (4)0.18437 (8)0.0467 (5)
H40.3085960.1119570.2197930.056*
C50.29339 (17)0.2522 (3)0.04951 (7)0.0352 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0548 (8)0.0447 (8)0.0471 (7)0.0127 (6)0.0200 (6)0.0100 (6)
O20.0495 (8)0.0427 (7)0.0447 (7)0.0166 (6)0.0143 (6)0.0111 (5)
O40.0593 (9)0.0538 (9)0.0510 (8)0.0241 (7)0.0191 (7)0.0067 (6)
O50.0472 (7)0.0363 (7)0.0422 (7)0.0095 (6)0.0135 (6)0.0035 (5)
C60.0347 (9)0.0257 (9)0.0354 (9)0.0018 (7)0.0015 (7)0.0016 (6)
C70.0366 (9)0.0313 (9)0.0414 (9)0.0012 (7)0.0042 (7)0.0037 (7)
C80.0417 (10)0.0330 (10)0.0520 (11)0.0082 (8)0.0004 (8)0.0018 (7)
C90.0478 (11)0.0326 (10)0.0442 (10)0.0009 (8)0.0011 (8)0.0075 (7)
C100.0440 (10)0.0368 (10)0.0379 (9)0.0027 (8)0.0070 (8)0.0027 (7)
C110.0348 (9)0.0260 (8)0.0391 (9)0.0022 (7)0.0040 (7)0.0027 (6)
C120.0364 (9)0.0292 (9)0.0377 (9)0.0004 (7)0.0070 (7)0.0017 (6)
O10.0544 (8)0.0446 (8)0.0433 (7)0.0161 (6)0.0182 (6)0.0118 (6)
N10.0440 (9)0.0358 (8)0.0468 (9)0.0067 (7)0.0077 (7)0.0038 (6)
N20.0490 (9)0.0394 (9)0.0413 (8)0.0063 (7)0.0155 (7)0.0026 (6)
N30.0468 (9)0.0466 (10)0.0521 (9)0.0164 (8)0.0173 (7)0.0122 (7)
C10.0338 (9)0.0312 (9)0.0364 (8)0.0002 (7)0.0066 (7)0.0001 (7)
C20.0412 (10)0.0367 (9)0.0365 (9)0.0019 (8)0.0104 (7)0.0006 (7)
C30.0500 (11)0.0384 (10)0.0418 (10)0.0030 (8)0.0064 (8)0.0069 (7)
C40.0584 (12)0.0461 (11)0.0392 (10)0.0058 (9)0.0183 (9)0.0060 (8)
C50.0360 (9)0.0307 (9)0.0391 (9)0.0022 (7)0.0069 (7)0.0001 (7)
Geometric parameters (Å, º) top
O3—C121.2291 (19)C10—H100.9300
O2—C121.313 (2)O1—C51.2352 (19)
O2—H2A1.1114N1—C31.321 (2)
O4—C71.347 (2)N1—C21.330 (2)
O4—H4A0.9473N2—C41.330 (2)
O5—C111.358 (2)N2—C11.333 (2)
O5—H5A0.9309N3—C51.319 (2)
C6—C111.410 (2)N3—H3A0.8828
C6—C71.420 (2)N3—H3B0.9144
C6—C121.466 (2)C1—C21.381 (2)
C7—C81.381 (2)C1—C51.496 (2)
C8—C91.371 (2)C2—H20.9300
C8—H80.9300C3—C41.385 (3)
C9—C101.381 (3)C3—H30.9300
C9—H90.9300C4—H40.9300
C10—C111.378 (2)
C12—O2—H2A115.1O3—C12—C6123.09 (15)
C7—O4—H4A107.6O2—C12—C6115.20 (14)
C11—O5—H5A105.5C3—N1—C2115.85 (15)
C11—C6—C7117.97 (14)C4—N2—C1115.72 (15)
C11—C6—C12123.48 (15)C5—N3—H3A117.5
C7—C6—C12118.55 (14)C5—N3—H3B120.2
O4—C7—C8117.80 (16)H3A—N3—H3B122.3
O4—C7—C6121.59 (15)N2—C1—C2122.16 (15)
C8—C7—C6120.61 (16)N2—C1—C5116.91 (14)
C9—C8—C7119.67 (17)C2—C1—C5120.93 (15)
C9—C8—H8120.2N1—C2—C1121.99 (15)
C7—C8—H8120.2N1—C2—H2119.0
C8—C9—C10121.32 (16)C1—C2—H2119.0
C8—C9—H9119.3N1—C3—C4122.49 (16)
C10—C9—H9119.3N1—C3—H3118.8
C11—C10—C9120.07 (16)C4—C3—H3118.8
C11—C10—H10120.0N2—C4—C3121.77 (16)
C9—C10—H10120.0N2—C4—H4119.1
O5—C11—C10115.66 (15)C3—C4—H4119.1
O5—C11—C6123.99 (14)O1—C5—N3124.09 (16)
C10—C11—C6120.35 (15)O1—C5—C1120.10 (14)
O3—C12—O2121.70 (15)N3—C5—C1115.81 (15)
C11—C6—C7—O4178.87 (15)C7—C6—C12—O33.5 (2)
C12—C6—C7—O41.4 (2)C11—C6—C12—O23.7 (2)
C11—C6—C7—C80.6 (2)C7—C6—C12—O2176.58 (14)
C12—C6—C7—C8179.15 (15)C4—N2—C1—C20.7 (3)
O4—C7—C8—C9178.93 (16)C4—N2—C1—C5179.28 (16)
C6—C7—C8—C90.6 (3)C3—N1—C2—C11.1 (3)
C7—C8—C9—C100.1 (3)N2—C1—C2—N10.5 (3)
C8—C9—C10—C110.4 (3)C5—C1—C2—N1179.47 (15)
C9—C10—C11—O5179.70 (15)C2—N1—C3—C40.4 (3)
C9—C10—C11—C60.4 (2)C1—N2—C4—C31.4 (3)
C7—C6—C11—O5179.77 (15)N1—C3—C4—N20.8 (3)
C12—C6—C11—O50.5 (2)N2—C1—C5—O1169.36 (16)
C7—C6—C11—C100.2 (2)C2—C1—C5—O110.6 (2)
C12—C6—C11—C10179.61 (16)N2—C1—C5—N310.6 (2)
C11—C6—C12—O3176.31 (16)C2—C1—C5—N3169.37 (16)
(Pyz_35DHBA) top
Crystal data top
C7H6O4·C5H5N3OF(000) = 576
Mr = 277.24Dx = 1.506 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 5.0262 (3) ÅCell parameters from 4461 reflections
b = 25.2701 (11) Åθ = 2.3–27.0°
c = 9.7106 (5) ŵ = 0.12 mm1
β = 97.492 (3)°T = 296 K
V = 1222.84 (11) Å3Block, colorless
Z = 40.23 × 0.18 × 0.16 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2259 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
φ and ω scansθmax = 27.1°, θmin = 2.3°
Absorption correction: multi-scan
Bruker AXS SADABS program
h = 56
Tmin = 0.973, Tmax = 0.981k = 3132
10147 measured reflectionsl = 1112
2677 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0581P)2 + 0.4176P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
2677 reflectionsΔρmax = 0.15 e Å3
201 parametersΔρmin = 0.26 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
C10.7152 (3)0.07063 (6)0.81374 (16)0.0311 (3)
C20.8607 (4)0.09207 (6)0.71523 (17)0.0375 (4)
H20.8385940.1276380.6919040.045*
C31.0541 (4)0.01251 (7)0.69110 (18)0.0407 (4)
H31.1707650.0091750.6499160.049*
C40.9104 (4)0.00895 (7)0.78978 (19)0.0439 (4)
H40.9337890.0444890.8131360.053*
C50.5225 (3)0.10536 (6)0.87752 (16)0.0344 (4)
C60.7002 (3)0.17708 (6)0.26205 (15)0.0296 (3)
C70.5911 (3)0.22364 (6)0.30452 (16)0.0337 (4)
H70.6356100.2560410.2682810.040*
C80.4135 (3)0.22086 (6)0.40251 (16)0.0344 (4)
C90.3463 (3)0.17281 (6)0.45713 (17)0.0349 (4)
H90.2286670.1715960.5234850.042*
C100.4554 (3)0.12651 (6)0.41227 (16)0.0337 (4)
C110.6346 (3)0.12845 (6)0.31483 (17)0.0345 (4)
H110.7096380.0974920.2852880.041*
C120.8917 (3)0.17874 (6)0.15695 (16)0.0321 (3)
H4A0.352 (5)0.2936 (10)0.412 (3)0.064 (7)*
H5A0.269 (6)0.0808 (11)0.523 (3)0.089 (9)*
H3A0.432 (4)0.0503 (9)1.004 (2)0.048 (6)*
H3B0.283 (4)0.1053 (8)1.014 (2)0.051 (6)*
H2A1.059 (5)0.2280 (9)0.055 (3)0.069 (7)*
N20.7391 (3)0.01997 (5)0.85234 (15)0.0382 (3)
N11.0315 (3)0.06284 (6)0.65319 (14)0.0387 (3)
N30.3986 (3)0.08439 (6)0.97651 (15)0.0396 (4)
O10.4864 (3)0.15084 (5)0.83340 (15)0.0544 (4)
O30.9916 (3)0.13964 (5)0.11251 (13)0.0440 (3)
O20.9400 (3)0.22726 (5)0.11761 (14)0.0492 (4)
O40.2972 (3)0.26537 (5)0.44612 (15)0.0526 (4)
O50.3948 (3)0.07791 (5)0.46020 (14)0.0490 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0325 (8)0.0297 (7)0.0334 (7)0.0010 (6)0.0129 (6)0.0012 (6)
C20.0427 (10)0.0313 (8)0.0423 (9)0.0015 (7)0.0198 (7)0.0036 (6)
C30.0461 (10)0.0354 (9)0.0454 (9)0.0041 (7)0.0238 (8)0.0013 (7)
C40.0562 (11)0.0288 (8)0.0521 (10)0.0042 (7)0.0280 (9)0.0038 (7)
C50.0379 (9)0.0291 (8)0.0389 (8)0.0003 (6)0.0156 (7)0.0029 (6)
C60.0287 (8)0.0317 (8)0.0308 (7)0.0005 (6)0.0131 (6)0.0002 (6)
C70.0369 (9)0.0288 (7)0.0398 (8)0.0016 (6)0.0214 (7)0.0005 (6)
C80.0390 (9)0.0301 (8)0.0385 (8)0.0013 (6)0.0217 (7)0.0048 (6)
C90.0376 (9)0.0363 (8)0.0353 (8)0.0043 (7)0.0219 (7)0.0022 (6)
C100.0380 (9)0.0314 (8)0.0344 (8)0.0029 (6)0.0151 (7)0.0032 (6)
C110.0379 (9)0.0301 (8)0.0391 (8)0.0037 (6)0.0190 (7)0.0008 (6)
C120.0318 (8)0.0333 (8)0.0343 (8)0.0024 (6)0.0157 (6)0.0014 (6)
N20.0459 (9)0.0301 (7)0.0430 (8)0.0012 (6)0.0223 (6)0.0023 (6)
N10.0429 (8)0.0365 (7)0.0413 (7)0.0001 (6)0.0224 (6)0.0016 (6)
N30.0444 (9)0.0351 (8)0.0445 (8)0.0036 (6)0.0257 (7)0.0003 (6)
O10.0710 (10)0.0314 (6)0.0697 (9)0.0100 (6)0.0430 (7)0.0072 (6)
O30.0479 (8)0.0393 (6)0.0514 (7)0.0056 (5)0.0308 (6)0.0020 (5)
O20.0591 (9)0.0375 (7)0.0609 (8)0.0049 (6)0.0452 (7)0.0086 (6)
O40.0685 (10)0.0295 (6)0.0716 (9)0.0006 (6)0.0538 (8)0.0044 (6)
O50.0643 (9)0.0313 (6)0.0594 (8)0.0018 (6)0.0380 (7)0.0068 (5)
Geometric parameters (Å, º) top
C1—N21.335 (2)C7—H70.9300
C1—C21.388 (2)C8—O41.3601 (18)
C1—C51.499 (2)C8—C91.384 (2)
C2—N11.335 (2)C9—C101.386 (2)
C2—H20.9300C9—H90.9300
C3—N11.325 (2)C10—O51.3620 (18)
C3—C41.384 (2)C10—C111.389 (2)
C3—H30.9300C11—H110.9300
C4—N21.334 (2)C12—O31.2128 (19)
C4—H40.9300C12—O21.3162 (19)
C5—O11.232 (2)N3—H3A0.91 (2)
C5—N31.323 (2)N3—H3B0.90 (2)
C6—C71.384 (2)O2—H2A0.91 (3)
C6—C111.388 (2)O4—H4A0.85 (3)
C6—C121.4920 (19)O5—H5A0.94 (3)
C7—C81.389 (2)
N2—C1—C2122.11 (14)O4—C8—C7120.81 (14)
N2—C1—C5119.01 (13)C9—C8—C7121.16 (14)
C2—C1—C5118.88 (14)C8—C9—C10119.58 (13)
N1—C2—C1121.54 (15)C8—C9—H9120.2
N1—C2—H2119.2C10—C9—H9120.2
C1—C2—H2119.2O5—C10—C9122.56 (13)
N1—C3—C4122.34 (15)O5—C10—C11117.29 (14)
N1—C3—H3118.8C9—C10—C11120.15 (14)
C4—C3—H3118.8C6—C11—C10119.29 (14)
N2—C4—C3121.79 (15)C6—C11—H11120.4
N2—C4—H4119.1C10—C11—H11120.4
C3—C4—H4119.1O3—C12—O2123.73 (14)
O1—C5—N3124.39 (15)O3—C12—C6123.66 (14)
O1—C5—C1118.44 (14)O2—C12—C6112.60 (13)
N3—C5—C1117.16 (14)C4—N2—C1115.93 (14)
C7—C6—C11121.35 (13)C3—N1—C2116.28 (13)
C7—C6—C12119.75 (13)C5—N3—H3A120.2 (13)
C11—C6—C12118.90 (13)C5—N3—H3B116.8 (13)
C6—C7—C8118.46 (14)H3A—N3—H3B123.0 (19)
C6—C7—H7120.8C12—O2—H2A112.1 (15)
C8—C7—H7120.8C8—O4—H4A113.5 (17)
O4—C8—C9118.03 (13)C10—O5—H5A110.7 (17)
(Pyz-Ferulic_acid) top
Crystal data top
C10H10O4·C5H5N3OZ = 2
Mr = 317.30F(000) = 332
Triclinic, P1Dx = 1.397 Mg m3
a = 7.4159 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.1690 (7) ÅCell parameters from 5994 reflections
c = 11.0335 (8) Åθ = 2.5–26.4°
α = 70.471 (3)°µ = 0.11 mm1
β = 76.142 (3)°T = 296 K
γ = 78.253 (4)°Block, yellow
V = 754.40 (9) Å30.23 × 0.19 × 0.17 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2632 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
φ and ω scansθmax = 26.5°, θmin = 2.0°
Absorption correction: multi-scan
Bruker AXS SADABS program
h = 99
Tmin = 0.976, Tmax = 0.982k = 1212
11332 measured reflectionsl = 1313
3118 independent reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0571P)2 + 0.1265P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.107(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.23 e Å3
3118 reflectionsΔρmin = 0.15 e Å3
226 parametersExtinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.036 (4)
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
C10.18688 (16)0.24623 (12)0.14500 (12)0.0399 (3)
C20.22192 (18)0.12192 (13)0.24235 (13)0.0452 (3)
H20.3343800.1022760.2723270.054*
C30.0563 (2)0.06323 (15)0.24598 (15)0.0591 (4)
H30.1447090.0009150.2782310.071*
C40.0922 (2)0.18745 (16)0.14933 (16)0.0607 (4)
H40.2045260.2067360.1192200.073*
C50.32803 (16)0.34795 (12)0.08814 (12)0.0418 (3)
C60.05299 (18)0.56029 (12)0.28478 (12)0.0424 (3)
C70.15110 (17)0.44463 (12)0.36515 (12)0.0415 (3)
H70.2742750.4476190.3684770.050*
C80.06773 (17)0.32654 (12)0.43929 (11)0.0399 (3)
C90.11862 (17)0.32108 (13)0.43606 (12)0.0432 (3)
C100.21494 (19)0.43527 (15)0.35648 (14)0.0517 (3)
H100.3383400.4327390.3532960.062*
C110.13009 (19)0.55336 (14)0.28144 (13)0.0498 (3)
H110.1969700.6289490.2281420.060*
C120.1413 (2)0.68512 (13)0.20393 (13)0.0469 (3)
H120.0697490.7552700.1493200.056*
C130.3111 (2)0.70931 (14)0.19984 (14)0.0523 (3)
H130.3848230.6418730.2547540.063*
C140.38923 (19)0.83643 (13)0.11359 (13)0.0481 (3)
C150.3492 (2)0.20444 (17)0.51565 (17)0.0642 (4)
H15A0.4164550.2222560.4270750.096*
H15B0.3974790.1134000.5674820.096*
H15C0.3642300.2752540.5508000.096*
H2A0.607 (4)0.9356 (18)0.071 (3)0.198 (15)*
H3A0.366 (2)0.5282 (19)0.0454 (17)0.066 (5)*
H5A0.139 (3)0.145 (2)0.5552 (19)0.076 (6)*
H3B0.174 (3)0.4702 (18)0.0283 (17)0.064 (5)*
N10.02881 (15)0.28023 (12)0.09808 (11)0.0517 (3)
N20.09973 (16)0.02950 (11)0.29450 (11)0.0521 (3)
N30.28469 (18)0.46044 (12)0.00823 (12)0.0532 (3)
O10.47332 (13)0.32349 (10)0.13172 (10)0.0595 (3)
O20.55090 (16)0.85065 (11)0.12432 (12)0.0690 (3)
O30.29722 (15)0.92710 (10)0.03279 (10)0.0599 (3)
O40.15490 (12)0.20803 (9)0.51800 (10)0.0524 (3)
O50.20720 (14)0.20744 (11)0.50558 (10)0.0575 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0382 (6)0.0369 (6)0.0408 (6)0.0046 (5)0.0070 (5)0.0071 (5)
C20.0433 (6)0.0393 (6)0.0492 (7)0.0059 (5)0.0138 (5)0.0049 (5)
C30.0523 (8)0.0525 (8)0.0651 (9)0.0216 (6)0.0134 (7)0.0022 (7)
C40.0463 (7)0.0597 (8)0.0687 (9)0.0168 (6)0.0213 (7)0.0032 (7)
C50.0380 (6)0.0382 (6)0.0443 (6)0.0056 (5)0.0068 (5)0.0064 (5)
C60.0497 (7)0.0373 (6)0.0368 (6)0.0113 (5)0.0045 (5)0.0061 (5)
C70.0381 (6)0.0402 (6)0.0438 (6)0.0108 (5)0.0053 (5)0.0079 (5)
C80.0391 (6)0.0372 (6)0.0389 (6)0.0073 (5)0.0059 (5)0.0053 (5)
C90.0421 (6)0.0422 (6)0.0414 (6)0.0136 (5)0.0061 (5)0.0041 (5)
C100.0419 (7)0.0541 (8)0.0536 (8)0.0128 (6)0.0152 (6)0.0010 (6)
C110.0517 (7)0.0448 (7)0.0459 (7)0.0077 (6)0.0155 (6)0.0005 (5)
C120.0574 (8)0.0366 (6)0.0414 (6)0.0109 (5)0.0063 (5)0.0042 (5)
C130.0559 (8)0.0370 (6)0.0544 (8)0.0117 (6)0.0076 (6)0.0001 (5)
C140.0526 (7)0.0359 (6)0.0504 (7)0.0113 (5)0.0042 (6)0.0068 (5)
C150.0425 (7)0.0569 (8)0.0785 (10)0.0081 (6)0.0180 (7)0.0041 (7)
N10.0445 (6)0.0476 (6)0.0548 (6)0.0118 (5)0.0158 (5)0.0032 (5)
N20.0542 (7)0.0406 (6)0.0541 (7)0.0116 (5)0.0133 (5)0.0006 (5)
N30.0478 (6)0.0439 (6)0.0592 (7)0.0147 (5)0.0175 (5)0.0061 (5)
O10.0438 (5)0.0533 (6)0.0709 (6)0.0141 (4)0.0195 (5)0.0058 (5)
O20.0580 (6)0.0487 (6)0.0860 (8)0.0211 (5)0.0164 (5)0.0082 (5)
O30.0686 (7)0.0449 (5)0.0594 (6)0.0203 (5)0.0159 (5)0.0032 (4)
O40.0405 (5)0.0416 (5)0.0623 (6)0.0102 (4)0.0132 (4)0.0062 (4)
O50.0467 (5)0.0518 (6)0.0634 (6)0.0220 (4)0.0169 (5)0.0100 (5)
Geometric parameters (Å, º) top
C1—N11.3295 (16)C9—O51.3529 (15)
C1—C21.3826 (17)C9—C101.3823 (18)
C1—C51.5005 (16)C10—C111.3846 (19)
C2—N21.3307 (17)C10—H100.9300
C2—H20.9300C11—H110.9300
C3—N21.3248 (18)C12—C131.319 (2)
C3—C41.379 (2)C12—H120.9300
C3—H30.9300C13—C141.4598 (17)
C4—N11.3269 (18)C13—H130.9300
C4—H40.9300C14—O31.2635 (17)
C5—O11.2301 (15)C14—O21.2737 (18)
C5—N31.3203 (16)C15—O41.4280 (16)
C6—C111.3836 (19)C15—H15A0.9600
C6—C71.4009 (17)C15—H15B0.9600
C6—C121.4619 (17)C15—H15C0.9600
C7—C81.3772 (16)N3—H3A0.930 (19)
C7—H70.9300N3—H3B0.880 (18)
C8—O41.3698 (14)O2—H2A0.9802 (10)
C8—C91.4036 (17)O5—H5A0.86 (2)
N1—C1—C2121.80 (11)C9—C10—H10119.6
N1—C1—C5117.56 (10)C11—C10—H10119.6
C2—C1—C5120.64 (11)C6—C11—C10120.81 (12)
N2—C2—C1122.04 (12)C6—C11—H11119.6
N2—C2—H2119.0C10—C11—H11119.6
C1—C2—H2119.0C13—C12—C6127.23 (13)
N2—C3—C4122.35 (13)C13—C12—H12116.4
N2—C3—H3118.8C6—C12—H12116.4
C4—C3—H3118.8C12—C13—C14123.42 (13)
N1—C4—C3121.89 (13)C12—C13—H13118.3
N1—C4—H4119.1C14—C13—H13118.3
C3—C4—H4119.1O3—C14—O2122.61 (12)
O1—C5—N3124.25 (12)O3—C14—C13120.17 (13)
O1—C5—C1119.89 (11)O2—C14—C13117.21 (12)
N3—C5—C1115.86 (11)O4—C15—H15A109.5
C11—C6—C7118.47 (11)O4—C15—H15B109.5
C11—C6—C12120.15 (12)H15A—C15—H15B109.5
C7—C6—C12121.36 (12)O4—C15—H15C109.5
C8—C7—C6120.94 (11)H15A—C15—H15C109.5
C8—C7—H7119.5H15B—C15—H15C109.5
C6—C7—H7119.5C4—N1—C1116.11 (11)
O4—C8—C7124.61 (11)C3—N2—C2115.79 (11)
O4—C8—C9115.26 (10)C5—N3—H3A119.4 (10)
C7—C8—C9120.13 (11)C5—N3—H3B116.7 (11)
O5—C9—C10118.40 (11)H3A—N3—H3B123.6 (15)
O5—C9—C8122.79 (11)C14—O2—H2A120.2 (19)
C10—C9—C8118.79 (11)C8—O4—C15117.07 (10)
C9—C10—C11120.85 (12)C9—O5—H5A111.2 (13)
(PYZ_pTSA) top
Crystal data top
C7H7O3S·C5H6N3OZ = 4
Mr = 295.31F(000) = 616
Triclinic, P1Dx = 1.468 Mg m3
a = 7.6458 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.9985 (11) ÅCell parameters from 4207 reflections
c = 18.027 (2) Åθ = 2.3–26.0°
α = 103.727 (5)°µ = 0.26 mm1
β = 92.711 (6)°T = 296 K
γ = 91.656 (5)°Block, yellow
V = 1336.1 (3) Å30.12 × 0.10 × 0.08 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3492 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.052
φ and ω scansθmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan
Bruker AXS SADABS program
h = 99
Tmin = 0.970, Tmax = 0.980k = 1212
20584 measured reflectionsl = 2222
5502 independent reflections
Refinement top
Refinement on F236 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.163 w = 1/[σ2(Fo2) + (0.0913P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.004
5502 reflectionsΔρmax = 0.34 e Å3
443 parametersΔρmin = 0.45 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)
C10.8272 (3)0.4203 (2)0.93810 (13)0.0322 (5)
C20.8683 (3)0.2905 (2)0.89836 (14)0.0400 (6)
H20.8436560.2135520.9172600.048*
C30.9811 (3)0.3857 (3)0.80406 (14)0.0431 (6)
H31.0321020.3750610.7572930.052*
C40.9415 (3)0.5147 (3)0.84624 (15)0.0452 (6)
H40.9696650.5917720.8280600.054*
C50.7356 (3)0.4359 (2)1.01158 (14)0.0351 (5)
C60.6610 (3)0.9132 (2)0.93679 (13)0.0343 (5)
C70.6045 (3)0.7824 (2)0.89799 (14)0.0385 (6)
H70.6298760.7067530.9176320.046*
C80.4777 (3)0.8733 (3)0.80262 (15)0.0466 (7)
H80.4171080.8604870.7553400.056*
C90.5323 (4)1.0034 (3)0.84333 (15)0.0477 (7)
H90.5047691.0788580.8238410.057*
C100.7661 (3)0.9338 (2)1.01163 (14)0.0356 (6)
C110.1067 (3)0.8432 (2)0.68057 (13)0.0336 (5)
C120.1879 (3)0.9471 (3)0.65402 (15)0.0457 (6)
H120.1509281.0368930.6683300.055*
C130.3243 (4)0.9159 (4)0.60612 (17)0.0598 (8)
H130.3776580.9857160.5879960.072*
C140.3837 (4)0.7839 (4)0.58437 (15)0.0582 (8)
C150.3004 (4)0.6814 (3)0.61160 (16)0.0551 (8)
H150.3378430.5917230.5974250.066*
C160.1629 (3)0.7097 (3)0.65928 (15)0.0438 (6)
H160.1086560.6397000.6769350.053*
C170.5386 (4)0.7521 (5)0.5348 (2)0.0924 (13)
H17A0.5556970.8233300.5079540.139*
H17B0.5165360.6652310.4985180.139*
H17C0.6419120.7475840.5663450.139*
C180.6133 (3)0.3468 (3)0.68533 (13)0.0350 (5)
C190.6906 (4)0.4507 (3)0.65800 (15)0.0483 (7)
H190.6518660.5400990.6719180.058*
C200.8268 (4)0.4199 (4)0.60951 (17)0.0633 (9)
H200.8769080.4894540.5901710.076*
C210.8902 (4)0.2900 (4)0.58910 (16)0.0623 (9)
C220.8103 (4)0.1867 (3)0.61726 (16)0.0562 (8)
H220.8499650.0976030.6035830.067*
C230.6727 (3)0.2141 (3)0.66526 (14)0.0451 (6)
H230.6208060.1442110.6837940.054*
C241.0444 (4)0.2591 (5)0.5389 (2)0.0976 (14)
H24A1.0193820.1750430.5006760.146*
H24B1.1469340.2494580.5697220.146*
H24C1.0644820.3332900.5145120.146*
H1A0.965 (4)0.187 (3)0.8065 (18)0.073 (10)*
H3A0.736 (3)0.637 (3)1.0254 (13)0.038 (7)*
H4A0.476 (4)0.683 (3)0.8033 (19)0.076 (11)*
H6A0.760 (3)1.132 (3)1.0309 (14)0.045 (8)*
H3B0.649 (4)0.575 (3)1.0871 (16)0.052 (8)*
H6B0.860 (3)1.076 (2)1.0942 (15)0.041 (7)*
N10.9443 (3)0.2780 (2)0.83212 (13)0.0454 (6)
N20.8639 (3)0.5313 (2)0.91233 (12)0.0405 (5)
N30.7020 (3)0.5631 (2)1.04678 (13)0.0396 (5)
N40.5125 (3)0.7666 (2)0.83154 (13)0.0441 (5)
N50.6239 (3)1.0236 (2)0.91020 (12)0.0416 (5)
N60.8067 (3)1.0628 (2)1.04786 (14)0.0419 (5)
O10.6975 (2)0.33240 (17)1.03446 (10)0.0495 (5)
O20.8079 (3)0.83300 (17)1.03494 (11)0.0528 (5)
O3A0.0083 (9)0.8340 (7)0.8106 (3)0.0674 (18)0.630 (10)
O4A0.0957 (7)1.0191 (3)0.7578 (3)0.065 (2)0.630 (10)
O5A0.2146 (5)0.7931 (6)0.7061 (2)0.0642 (17)0.630 (10)
O6A0.5200 (7)0.3700 (8)0.8221 (3)0.0868 (19)0.837 (15)
O7A0.3864 (6)0.5167 (5)0.7517 (3)0.0548 (12)0.837 (15)
O8A0.3066 (7)0.2789 (4)0.7209 (4)0.0819 (19)0.837 (15)
O3B0.2103 (8)0.9111 (15)0.7055 (4)0.093 (5)0.370 (10)
O4B0.076 (2)0.7824 (12)0.7852 (9)0.115 (7)0.370 (10)
O5B0.0144 (14)1.0111 (8)0.7994 (5)0.081 (3)0.370 (10)
O6B0.453 (6)0.310 (4)0.802 (2)0.109 (13)0.163 (15)
O7B0.452 (5)0.522 (3)0.779 (2)0.102 (12)0.163 (15)
O8B0.291 (3)0.340 (5)0.7007 (12)0.117 (13)0.163 (15)
S10.06309 (8)0.87955 (6)0.74478 (3)0.0400 (2)
S20.44210 (8)0.37959 (6)0.74898 (4)0.0385 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0284 (11)0.0304 (13)0.0370 (13)0.0007 (9)0.0008 (10)0.0070 (10)
C20.0402 (13)0.0328 (14)0.0475 (15)0.0012 (11)0.0062 (12)0.0098 (11)
C30.0345 (13)0.0564 (18)0.0382 (14)0.0023 (12)0.0063 (11)0.0099 (13)
C40.0518 (16)0.0437 (16)0.0443 (15)0.0012 (12)0.0082 (12)0.0176 (12)
C50.0320 (12)0.0303 (13)0.0430 (14)0.0008 (10)0.0015 (10)0.0087 (11)
C60.0307 (12)0.0329 (13)0.0411 (13)0.0021 (10)0.0094 (10)0.0105 (11)
C70.0367 (13)0.0319 (14)0.0465 (14)0.0036 (10)0.0046 (11)0.0080 (11)
C80.0408 (14)0.0558 (18)0.0424 (15)0.0000 (13)0.0009 (12)0.0106 (13)
C90.0529 (16)0.0475 (17)0.0474 (16)0.0009 (13)0.0015 (13)0.0213 (13)
C100.0356 (12)0.0302 (13)0.0419 (14)0.0011 (10)0.0045 (11)0.0098 (11)
C110.0307 (12)0.0330 (13)0.0349 (12)0.0008 (10)0.0000 (10)0.0040 (10)
C120.0446 (14)0.0462 (16)0.0476 (15)0.0037 (12)0.0022 (12)0.0143 (12)
C130.0442 (16)0.083 (2)0.0567 (18)0.0177 (16)0.0024 (14)0.0280 (17)
C140.0337 (14)0.097 (3)0.0385 (15)0.0005 (15)0.0008 (12)0.0053 (16)
C150.0447 (15)0.0591 (19)0.0522 (17)0.0138 (14)0.0005 (13)0.0062 (14)
C160.0418 (14)0.0381 (15)0.0489 (15)0.0005 (11)0.0040 (12)0.0052 (12)
C170.0476 (19)0.167 (4)0.057 (2)0.008 (2)0.0144 (16)0.014 (2)
C180.0291 (11)0.0407 (14)0.0327 (12)0.0024 (10)0.0006 (10)0.0050 (11)
C190.0458 (15)0.0498 (17)0.0489 (15)0.0104 (12)0.0005 (13)0.0128 (13)
C200.0464 (16)0.093 (3)0.0536 (18)0.0219 (17)0.0028 (14)0.0258 (17)
C210.0325 (14)0.112 (3)0.0380 (15)0.0008 (17)0.0022 (12)0.0110 (17)
C220.0449 (16)0.069 (2)0.0486 (16)0.0180 (15)0.0052 (13)0.0001 (15)
C230.0423 (14)0.0457 (16)0.0449 (15)0.0027 (12)0.0036 (12)0.0057 (12)
C240.0461 (19)0.186 (4)0.057 (2)0.003 (2)0.0167 (16)0.018 (2)
N10.0464 (13)0.0373 (13)0.0473 (13)0.0045 (10)0.0067 (10)0.0015 (11)
N20.0464 (12)0.0323 (11)0.0449 (12)0.0028 (9)0.0080 (10)0.0120 (9)
N30.0463 (13)0.0319 (12)0.0418 (13)0.0042 (10)0.0119 (10)0.0089 (10)
N40.0410 (12)0.0419 (14)0.0449 (13)0.0020 (10)0.0058 (10)0.0009 (11)
N50.0448 (12)0.0359 (12)0.0467 (12)0.0007 (9)0.0055 (10)0.0148 (10)
N60.0479 (13)0.0337 (13)0.0436 (13)0.0004 (10)0.0032 (11)0.0096 (10)
O10.0623 (12)0.0329 (10)0.0582 (11)0.0015 (8)0.0193 (9)0.0172 (9)
O20.0645 (12)0.0327 (10)0.0620 (12)0.0028 (9)0.0113 (10)0.0159 (9)
O3A0.084 (3)0.084 (5)0.042 (2)0.008 (3)0.003 (2)0.028 (3)
O4A0.088 (4)0.0278 (18)0.081 (4)0.018 (2)0.035 (3)0.0083 (19)
O5A0.0374 (18)0.073 (4)0.069 (2)0.0100 (19)0.0091 (16)0.011 (2)
O6A0.059 (2)0.163 (6)0.0508 (19)0.040 (3)0.0193 (17)0.043 (3)
O7A0.058 (2)0.034 (2)0.069 (2)0.0084 (17)0.0067 (16)0.0041 (19)
O8A0.049 (2)0.045 (2)0.134 (5)0.0157 (14)0.039 (3)0.0196 (18)
O3B0.040 (4)0.182 (16)0.061 (4)0.039 (6)0.003 (3)0.030 (6)
O4B0.175 (15)0.056 (7)0.151 (14)0.054 (7)0.128 (12)0.071 (8)
O5B0.084 (6)0.061 (4)0.075 (5)0.001 (4)0.014 (5)0.031 (4)
O6B0.15 (3)0.105 (19)0.12 (2)0.088 (17)0.097 (19)0.110 (18)
O7B0.11 (2)0.037 (11)0.13 (2)0.029 (13)0.062 (16)0.064 (14)
O8B0.024 (7)0.25 (3)0.034 (9)0.015 (16)0.015 (6)0.035 (16)
S10.0414 (4)0.0375 (4)0.0405 (4)0.0049 (3)0.0091 (3)0.0067 (3)
S20.0331 (3)0.0365 (4)0.0442 (4)0.0020 (3)0.0069 (3)0.0053 (3)
Geometric parameters (Å, º) top
C1—N21.329 (3)C17—H17A0.9600
C1—C21.379 (3)C17—H17B0.9600
C1—C51.505 (3)C17—H17C0.9600
C2—N11.334 (3)C18—C191.381 (4)
C2—H20.9300C18—C231.386 (3)
C3—N11.323 (3)C18—S21.768 (2)
C3—C41.382 (4)C19—C201.386 (4)
C3—H30.9300C19—H190.9300
C4—N21.333 (3)C20—C211.372 (4)
C4—H40.9300C20—H200.9300
C5—O11.234 (3)C21—C221.393 (4)
C5—N31.319 (3)C21—C241.514 (4)
C6—N51.336 (3)C22—C231.386 (4)
C6—C71.375 (3)C22—H220.9300
C6—C101.505 (3)C23—H230.9300
C7—N41.334 (3)C24—H24A0.9600
C7—H70.9300C24—H24B0.9600
C8—N41.321 (3)C24—H24C0.9600
C8—C91.376 (4)N1—H1A0.94 (3)
C8—H80.9300N3—H3A0.94 (3)
C9—N51.335 (3)N3—H3B0.83 (3)
C9—H90.9300N4—H4A0.90 (3)
C10—O21.225 (3)N6—H6A0.89 (3)
C10—N61.321 (3)N6—H6B0.89 (3)
C11—C121.385 (3)O3A—S11.418 (6)
C11—C161.385 (3)O4A—S11.391 (3)
C11—S11.769 (2)O5A—S11.468 (3)
C12—C131.381 (4)O6A—S21.446 (5)
C12—H120.9300O7A—S21.438 (5)
C13—C141.381 (4)O8A—S21.411 (4)
C13—H130.9300O3B—S11.385 (6)
C14—C151.388 (4)O4B—S11.349 (11)
C14—C171.514 (4)O5B—S11.528 (7)
C15—C161.382 (4)O6B—S21.31 (2)
C15—H150.9300O7B—S21.40 (2)
C16—H160.9300O8B—S21.399 (18)
N2—C1—C2121.5 (2)C18—C19—H19120.5
N2—C1—C5119.4 (2)C20—C19—H19120.5
C2—C1—C5119.1 (2)C21—C20—C19122.2 (3)
N1—C2—C1118.3 (2)C21—C20—H20118.9
N1—C2—H2120.9C19—C20—H20118.9
C1—C2—H2120.9C20—C21—C22117.9 (3)
N1—C3—C4118.1 (2)C20—C21—C24121.6 (4)
N1—C3—H3121.0C22—C21—C24120.5 (4)
C4—C3—H3121.0C23—C22—C21121.3 (3)
N2—C4—C3121.7 (2)C23—C22—H22119.4
N2—C4—H4119.2C21—C22—H22119.4
C3—C4—H4119.2C22—C23—C18119.3 (3)
O1—C5—N3125.0 (2)C22—C23—H23120.4
O1—C5—C1119.4 (2)C18—C23—H23120.4
N3—C5—C1115.7 (2)C21—C24—H24A109.5
N5—C6—C7121.8 (2)C21—C24—H24B109.5
N5—C6—C10118.7 (2)H24A—C24—H24B109.5
C7—C6—C10119.5 (2)C21—C24—H24C109.5
N4—C7—C6118.5 (2)H24A—C24—H24C109.5
N4—C7—H7120.8H24B—C24—H24C109.5
C6—C7—H7120.8C3—N1—C2122.0 (2)
N4—C8—C9119.2 (3)C3—N1—H1A123.2 (19)
N4—C8—H8120.4C2—N1—H1A114.7 (19)
C9—C8—H8120.4C1—N2—C4118.4 (2)
N5—C9—C8121.4 (2)C5—N3—H3A119.6 (14)
N5—C9—H9119.3C5—N3—H3B117.8 (19)
C8—C9—H9119.3H3A—N3—H3B123 (2)
O2—C10—N6124.5 (2)C8—N4—C7121.3 (2)
O2—C10—C6119.4 (2)C8—N4—H4A117 (2)
N6—C10—C6116.1 (2)C7—N4—H4A122 (2)
C12—C11—C16120.0 (2)C9—N5—C6117.9 (2)
C12—C11—S1120.87 (19)C10—N6—H6A119.8 (17)
C16—C11—S1119.03 (19)C10—N6—H6B116.8 (16)
C13—C12—C11119.3 (3)H6A—N6—H6B122 (2)
C13—C12—H12120.3O4B—S1—O3B119.6 (7)
C11—C12—H12120.3O4A—S1—O3A115.2 (3)
C12—C13—C14121.8 (3)O4A—S1—O5A111.8 (3)
C12—C13—H13119.1O3A—S1—O5A108.9 (3)
C14—C13—H13119.1O4B—S1—O5B107.3 (7)
C13—C14—C15117.9 (3)O3B—S1—O5B109.1 (5)
C13—C14—C17121.4 (3)O4B—S1—C11110.5 (5)
C15—C14—C17120.7 (3)O3B—S1—C11108.4 (3)
C16—C15—C14121.5 (3)O4A—S1—C11108.52 (17)
C16—C15—H15119.3O3A—S1—C11106.6 (3)
C14—C15—H15119.3O5A—S1—C11105.22 (15)
C15—C16—C11119.4 (3)O5B—S1—C11100.1 (3)
C15—C16—H16120.3O6B—S2—O7B112.9 (19)
C11—C16—H16120.3O6B—S2—O8B111.6 (17)
C14—C17—H17A109.5O7B—S2—O8B110.8 (16)
C14—C17—H17B109.5O8A—S2—O7A112.2 (2)
H17A—C17—H17B109.5O8A—S2—O6A112.8 (3)
C14—C17—H17C109.5O7A—S2—O6A111.1 (3)
H17A—C17—H17C109.5O6B—S2—C18112.7 (12)
H17B—C17—H17C109.5O7B—S2—C18105.2 (11)
C19—C18—C23120.4 (2)O8B—S2—C18103.1 (9)
C19—C18—S2121.4 (2)O8A—S2—C18107.6 (2)
C23—C18—S2118.16 (19)O7A—S2—C18107.6 (2)
C18—C19—C20119.0 (3)O6A—S2—C18105.1 (2)
 

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