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Lamotrigine is a drug used in the treatment of epilepsy and related convulsive diseases. The drug in its free form is rather inadequate for pharmacological use due to poor absorption by the patient, which limits its bioavailability. On the other hand, the lamotrigine mol­ecule is an excellent hydrogen-bonding agent and this has been exploited intensively in the search for better formulations. The formulation presently commercialized (under the brand name Lamictal) is rather complex and includes a number of anions in addition to the active pharmaceutical ingredient (API). The title salts of lamotrigine, namely 3,5-di­amino-6-(2,3-di­chloro­phen­yl)-1,2,4-triazin-2-ium 2-[(2-carb­oxy­phen­yl)di­sul­fan­yl]benzoate monohydrate, C9H8Cl2N5+·C14H9O4S2-·H2O, (I), and the anhydrate, C9H8Cl2N5+·C14H9O4S2-, (II), contain a lamotriginium cation (L), a hydrogen di­thio­dibenzoate monoanion (D) and, in the case of (I), a disordered solvent water mol­ecule. Both L and D present their usual configurations severely twisted around their central C-C and S-S bonds, respectively. The supra­molecular structure generated by the many available donor and acceptor sites is characterized by a planar anti­symmetric motif of the form D-L-L-D, i.e. the structural building block. Although this characteristic motif is extremely similar in both structures, its conformation involves different donors and acceptors in its R22(8) central L-L homosynthon. The lateral R22(8) D-L hetero­synthons are, on the other hand, identical. These substructures are further connected by strong hydrogen bonds into broad two-dimensional structures, in turn weakly linked to each other. Even if the homo- and heterosynthons in (I) and (II) are rather frequent in lamotrigine structural chemistry, the composite tetra­meric synthon appears to be much less common. The occurrence of these motifs among lamotrigine salts and cocrystals is analyzed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616016090/fp3034sup1.cif
Contains datablocks I, II, gobal

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016090/fp3034Isup5.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229616016090/fp3034sup4.pdf
Comparsion geometry table

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016090/fp3034IIsup6.hkl
Contains datablock II

CCDC references: 1509538; 1509537

Computing details top

For both compounds, data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008). Software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) andPLATON (Spek, 2009) for (I); SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009) for (II).

(I) 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium 2-[(2-carboxyphenyl)disulfanyl]benzoate monohydrate top
Crystal data top
C9H8Cl2N5+·C14H9O4S2·H2OZ = 2
Mr = 580.45F(000) = 596
Triclinic, P1Dx = 1.540 Mg m3
a = 8.0598 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.3474 (13) ÅCell parameters from 1591 reflections
c = 13.4484 (10) Åθ = 4.0–24.6°
α = 100.996 (7)°µ = 0.47 mm1
β = 98.101 (7)°T = 294 K
γ = 103.659 (8)°Prism, pale_yellow
V = 1252.1 (2) Å30.50 × 0.25 × 0.15 mm
Data collection top
Oxford Diffraction Gemini CCD S Ultra
diffractometer
3744 reflections with I > 2σ(I)
ω scans, thick slicesRint = 0.035
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
θmax = 29.3°, θmin = 3.7°
Tmin = 0.84, Tmax = 0.95h = 109
11193 measured reflectionsk = 1616
5794 independent reflectionsl = 1817
Refinement top
Refinement on F28 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.057H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.166 w = 1/[σ2(Fo2) + (0.0716P)2 + 0.7292P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
5794 reflectionsΔρmax = 0.78 e Å3
356 parametersΔρmin = 0.42 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)
S110.77327 (12)0.07472 (7)0.28054 (7)0.0412 (2)
O110.8359 (3)0.2817 (2)0.2858 (2)0.0429 (6)
O210.7123 (3)0.4436 (2)0.1645 (2)0.0466 (6)
H21O0.735 (5)0.483 (3)0.207 (2)0.056*
C110.6798 (4)0.1567 (3)0.1521 (3)0.0352 (7)
C210.6092 (4)0.1083 (3)0.0785 (3)0.0450 (9)
H210.60960.03170.09640.054*
C310.5371 (5)0.1712 (3)0.0220 (3)0.0487 (9)
H310.49060.13690.07100.058*
C410.5354 (5)0.2851 (3)0.0481 (3)0.0467 (9)
H410.48620.32830.11480.056*
C510.6058 (4)0.3352 (3)0.0239 (3)0.0397 (8)
H510.60410.41200.00510.048*
C610.6799 (4)0.2730 (3)0.1249 (3)0.0326 (7)
C710.7506 (4)0.3306 (3)0.1995 (3)0.0367 (8)
S120.69471 (11)0.07312 (7)0.29397 (7)0.0398 (2)
O120.6162 (3)0.2656 (2)0.3413 (2)0.0481 (6)
O220.7138 (3)0.43096 (18)0.29926 (17)0.0362 (5)
C120.8473 (4)0.1655 (3)0.2412 (2)0.0315 (7)
C220.9662 (4)0.1253 (3)0.1894 (3)0.0391 (8)
H220.96810.04930.18330.047*
C321.0812 (4)0.1955 (3)0.1472 (3)0.0433 (8)
H321.16130.16720.11420.052*
C421.0780 (5)0.3079 (3)0.1537 (3)0.0465 (9)
H421.15600.35570.12550.056*
C520.9576 (4)0.3485 (3)0.2025 (3)0.0370 (8)
H520.95340.42360.20550.044*
C620.8422 (4)0.2791 (3)0.2476 (2)0.0309 (7)
C720.7146 (4)0.3283 (3)0.2994 (2)0.0333 (7)
Cl10.16354 (15)0.88548 (10)0.09415 (8)0.0631 (3)
Cl20.18343 (14)0.64446 (9)0.12805 (8)0.0564 (3)
N10.4223 (4)0.5934 (2)0.3226 (2)0.0399 (7)
N20.4335 (3)0.4952 (2)0.3473 (2)0.0375 (7)
H20.519 (3)0.469 (3)0.334 (3)0.045*
N30.3547 (4)0.3462 (3)0.4241 (2)0.0470 (8)
H3A0.287 (4)0.300 (2)0.449 (3)0.056*
H3B0.427 (4)0.315 (3)0.400 (3)0.056*
N40.1980 (3)0.4814 (2)0.43416 (19)0.0319 (6)
N50.0477 (4)0.6160 (3)0.4291 (3)0.0423 (7)
H5A0.026 (3)0.581 (3)0.458 (3)0.051*
H5B0.008 (4)0.657 (3)0.395 (2)0.051*
C10.3283 (4)0.4407 (3)0.4026 (2)0.0349 (7)
C20.1771 (4)0.5749 (3)0.4059 (3)0.0334 (7)
C30.2964 (4)0.6347 (3)0.3510 (3)0.0379 (8)
C40.2864 (4)0.7472 (3)0.3306 (3)0.0387 (8)
C50.2374 (4)0.7607 (3)0.2317 (3)0.0438 (9)
C60.2278 (4)0.8680 (3)0.2161 (3)0.0435 (9)
C70.2656 (4)0.9625 (4)0.3006 (3)0.0513 (10)
H70.26081.03430.29060.062*
C80.3099 (5)0.9469 (3)0.3983 (3)0.0512 (9)
H80.33081.00920.45400.061*
C90.3249 (4)0.8428 (3)0.4180 (3)0.0364 (8)
H90.35830.83530.48490.044*
O1WA0.0946 (5)0.1640 (4)0.4904 (3)0.0521 (10)0.686 (4)
O1WB0.2255 (12)0.1963 (8)0.5250 (7)0.0521 (10)0.314 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S110.0566 (5)0.0269 (4)0.0445 (5)0.0196 (4)0.0087 (4)0.0093 (4)
O110.0468 (14)0.0345 (13)0.0537 (16)0.0202 (11)0.0079 (12)0.0148 (12)
O210.0675 (16)0.0252 (13)0.0543 (16)0.0198 (11)0.0161 (13)0.0142 (11)
C110.0354 (17)0.0253 (16)0.049 (2)0.0136 (13)0.0119 (15)0.0095 (15)
C210.045 (2)0.0317 (19)0.062 (2)0.0173 (15)0.0090 (17)0.0114 (18)
C310.054 (2)0.042 (2)0.054 (2)0.0204 (17)0.0032 (18)0.0169 (19)
C410.050 (2)0.041 (2)0.045 (2)0.0096 (16)0.0078 (17)0.0046 (17)
C510.0462 (19)0.0267 (17)0.052 (2)0.0123 (14)0.0203 (16)0.0109 (16)
C610.0348 (16)0.0235 (16)0.0436 (19)0.0103 (12)0.0150 (14)0.0097 (14)
C710.0359 (17)0.0281 (17)0.057 (2)0.0174 (14)0.0185 (16)0.0169 (17)
S120.0536 (5)0.0261 (4)0.0491 (5)0.0200 (4)0.0215 (4)0.0114 (4)
O120.0613 (16)0.0322 (13)0.0687 (18)0.0268 (11)0.0347 (14)0.0203 (13)
O220.0475 (13)0.0245 (11)0.0441 (13)0.0186 (10)0.0174 (10)0.0087 (10)
C120.0409 (17)0.0258 (16)0.0306 (16)0.0149 (13)0.0066 (13)0.0059 (13)
C220.0474 (19)0.0311 (18)0.046 (2)0.0230 (15)0.0140 (16)0.0078 (15)
C320.0443 (19)0.043 (2)0.050 (2)0.0221 (16)0.0208 (17)0.0069 (17)
C420.054 (2)0.042 (2)0.049 (2)0.0154 (17)0.0221 (18)0.0114 (17)
C520.0467 (19)0.0267 (17)0.0400 (19)0.0135 (14)0.0118 (15)0.0064 (15)
C620.0393 (17)0.0232 (15)0.0319 (16)0.0141 (13)0.0047 (13)0.0047 (13)
C720.0414 (18)0.0271 (17)0.0373 (18)0.0181 (14)0.0116 (14)0.0074 (14)
Cl10.0787 (7)0.0722 (7)0.0600 (7)0.0421 (6)0.0246 (5)0.0320 (6)
Cl20.0740 (7)0.0533 (6)0.0474 (6)0.0274 (5)0.0159 (5)0.0090 (5)
N10.0438 (16)0.0329 (15)0.0527 (18)0.0194 (12)0.0203 (14)0.0138 (14)
N20.0378 (15)0.0361 (16)0.0469 (17)0.0196 (12)0.0174 (13)0.0111 (13)
N30.071 (2)0.0416 (18)0.0484 (19)0.0381 (16)0.0261 (16)0.0192 (15)
N40.0430 (15)0.0295 (14)0.0315 (14)0.0188 (12)0.0136 (12)0.0114 (12)
N50.0396 (16)0.0386 (17)0.065 (2)0.0226 (13)0.0246 (15)0.0257 (15)
C10.0469 (19)0.0323 (18)0.0294 (16)0.0172 (14)0.0102 (14)0.0061 (14)
C20.0338 (16)0.0293 (17)0.0401 (18)0.0106 (13)0.0103 (14)0.0103 (14)
C30.0393 (18)0.0360 (18)0.046 (2)0.0178 (14)0.0124 (15)0.0149 (16)
C40.0312 (17)0.043 (2)0.050 (2)0.0160 (14)0.0187 (15)0.0159 (17)
C50.0370 (18)0.049 (2)0.051 (2)0.0160 (16)0.0222 (16)0.0089 (18)
C60.0334 (18)0.044 (2)0.065 (2)0.0185 (15)0.0216 (17)0.0238 (19)
C70.0342 (19)0.055 (2)0.070 (3)0.0143 (16)0.0125 (18)0.024 (2)
C80.056 (2)0.039 (2)0.058 (2)0.0161 (17)0.0118 (19)0.0065 (19)
C90.0331 (16)0.0216 (15)0.055 (2)0.0095 (12)0.0132 (15)0.0048 (15)
O1WA0.056 (2)0.069 (3)0.047 (2)0.030 (2)0.0202 (19)0.0288 (19)
O1WB0.056 (2)0.069 (3)0.047 (2)0.030 (2)0.0202 (19)0.0288 (19)
Geometric parameters (Å, º) top
S11—C111.783 (4)C52—H520.9300
S11—S122.0538 (11)C62—C721.499 (4)
O11—C711.223 (4)Cl1—C61.718 (4)
O21—C711.330 (4)Cl2—C51.721 (4)
O21—H21O0.850 (10)N1—C31.310 (4)
C11—C211.374 (5)N1—N21.336 (4)
C11—C611.413 (4)N2—C11.351 (4)
C21—C311.390 (5)N2—H20.847 (10)
C21—H210.9300N3—C11.311 (4)
C31—C411.380 (5)N3—H3A0.841 (10)
C31—H310.9300N3—H3B0.843 (10)
C41—C511.371 (5)N4—C21.322 (4)
C41—H410.9300N4—C11.353 (4)
C51—C611.395 (5)N5—C21.313 (4)
C51—H510.9300N5—H5A0.837 (10)
C61—C711.463 (5)N5—H5B0.840 (10)
S12—C121.792 (3)C2—C31.445 (4)
O12—C721.245 (4)C3—C41.484 (5)
O22—C721.269 (4)C4—C51.385 (5)
C12—C221.389 (4)C4—C91.438 (5)
C12—C621.399 (4)C5—C61.399 (5)
C22—C321.374 (5)C6—C71.406 (5)
C22—H220.9300C7—C81.373 (5)
C32—C421.380 (5)C7—H70.9300
C32—H320.9300C8—C91.390 (5)
C42—C521.382 (4)C8—H80.9300
C42—H420.9300C9—H90.9300
C52—C621.395 (4)
C11—S11—S12105.99 (11)O12—C72—O22123.7 (3)
C71—O21—H21O118 (3)O12—C72—C62117.5 (3)
C21—C11—C61119.2 (3)O22—C72—C62118.8 (3)
C21—C11—S11121.1 (3)C3—N1—N2116.7 (3)
C61—C11—S11119.7 (3)N1—N2—C1123.8 (2)
C11—C21—C31121.6 (3)N1—N2—H2119 (2)
C11—C21—H21119.2C1—N2—H2117 (2)
C31—C21—H21119.2C1—N3—H3A125 (2)
C41—C31—C21119.0 (3)C1—N3—H3B123 (2)
C41—C31—H31120.5H3A—N3—H3B110 (2)
C21—C31—H31120.5C2—N4—C1116.5 (3)
C51—C41—C31120.4 (4)C2—N5—H5A121 (2)
C51—C41—H41119.8C2—N5—H5B121 (2)
C31—C41—H41119.8H5A—N5—H5B112 (2)
C41—C51—C61121.2 (3)N3—C1—N2118.1 (3)
C41—C51—H51119.4N3—C1—N4120.7 (3)
C61—C51—H51119.4N2—C1—N4121.2 (3)
C51—C61—C11118.5 (3)N5—C2—N4119.9 (3)
C51—C61—C71119.3 (3)N5—C2—C3118.9 (3)
C11—C61—C71122.2 (3)N4—C2—C3121.2 (3)
O11—C71—O21122.4 (3)N1—C3—C2120.5 (3)
O11—C71—C61124.5 (3)N1—C3—C4118.2 (3)
O21—C71—C61113.1 (3)C2—C3—C4121.3 (3)
C12—S12—S11104.62 (10)C5—C4—C9120.3 (3)
C22—C12—C62118.9 (3)C5—C4—C3122.0 (3)
C22—C12—S12121.3 (2)C9—C4—C3117.6 (3)
C62—C12—S12119.7 (2)C4—C5—C6120.2 (3)
C32—C22—C12121.4 (3)C4—C5—Cl2120.0 (3)
C32—C22—H22119.3C6—C5—Cl2119.8 (3)
C12—C22—H22119.3C5—C6—C7120.3 (4)
C22—C32—C42120.2 (3)C5—C6—Cl1120.7 (3)
C22—C32—H32119.9C7—C6—Cl1119.0 (3)
C42—C32—H32119.9C8—C7—C6118.7 (4)
C32—C42—C52119.2 (3)C8—C7—H7120.6
C32—C42—H42120.4C6—C7—H7120.6
C52—C42—H42120.4C7—C8—C9123.3 (4)
C42—C52—C62121.4 (3)C7—C8—H8118.3
C42—C52—H52119.3C9—C8—H8118.3
C62—C52—H52119.3C8—C9—C4117.1 (3)
C52—C62—C12118.9 (3)C8—C9—H9121.4
C52—C62—C72118.8 (3)C4—C9—H9121.4
C12—C62—C72122.3 (3)
S12—S11—C11—C2113.6 (3)C12—C62—C72—O22177.7 (3)
S12—S11—C11—C61167.2 (2)C3—N1—N2—C12.9 (5)
C61—C11—C21—C310.3 (5)N1—N2—C1—N3178.4 (3)
S11—C11—C21—C31179.5 (3)N1—N2—C1—N42.4 (5)
C11—C21—C31—C410.5 (5)C2—N4—C1—N3177.7 (3)
C21—C31—C41—C510.8 (5)C2—N4—C1—N21.5 (5)
C31—C41—C51—C610.3 (5)C1—N4—C2—N5176.5 (3)
C41—C51—C61—C110.5 (5)C1—N4—C2—C34.5 (5)
C41—C51—C61—C71178.9 (3)N2—N1—C3—C20.2 (5)
C21—C11—C61—C510.8 (4)N2—N1—C3—C4176.3 (3)
S11—C11—C61—C51179.9 (2)N5—C2—C3—N1177.0 (3)
C21—C11—C61—C71179.1 (3)N4—C2—C3—N14.1 (5)
S11—C11—C61—C711.6 (4)N5—C2—C3—C46.6 (5)
C51—C61—C71—O11171.1 (3)N4—C2—C3—C4172.3 (3)
C11—C61—C71—O1110.6 (5)N1—C3—C4—C571.0 (4)
C51—C61—C71—O219.3 (4)C2—C3—C4—C5112.5 (4)
C11—C61—C71—O21169.1 (3)N1—C3—C4—C9110.8 (4)
S11—S12—C12—C229.4 (3)C2—C3—C4—C965.7 (4)
S11—S12—C12—C62173.6 (2)C9—C4—C5—C61.1 (5)
C62—C12—C22—C321.8 (5)C3—C4—C5—C6179.3 (3)
S12—C12—C22—C32178.8 (3)C9—C4—C5—Cl2177.5 (2)
C12—C22—C32—C421.4 (6)C3—C4—C5—Cl20.7 (4)
C22—C32—C42—C520.3 (6)C4—C5—C6—C70.8 (5)
C32—C42—C52—C621.6 (5)Cl2—C5—C6—C7177.7 (2)
C42—C52—C62—C121.1 (5)C4—C5—C6—Cl1178.9 (2)
C42—C52—C62—C72180.0 (3)Cl2—C5—C6—Cl10.3 (4)
C22—C12—C62—C520.5 (5)C5—C6—C7—C80.7 (5)
S12—C12—C62—C52177.6 (2)Cl1—C6—C7—C8177.3 (3)
C22—C12—C62—C72178.3 (3)C6—C7—C8—C92.2 (5)
S12—C12—C62—C721.2 (4)C7—C8—C9—C41.9 (5)
C52—C62—C72—O12178.1 (3)C5—C4—C9—C80.2 (4)
C12—C62—C72—O123.1 (5)C3—C4—C9—C8178.0 (3)
C52—C62—C72—O221.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O21—H21O···O22i0.85 (1)1.78 (2)2.599 (3)162 (4)
C21—H21···S120.932.643.181 (4)118
C22—H22···S110.932.593.146 (4)119
N2—H2···O220.85 (1)1.84 (1)2.686 (3)172 (4)
N3—H3A···O1WA0.84 (1)2.22 (1)3.052 (5)172 (4)
N3—H3A···O1WB0.84 (1)1.81 (2)2.607 (9)157 (4)
N3—H3B···O120.84 (1)1.98 (1)2.811 (4)171 (3)
N5—H5A···N4ii0.84 (1)2.26 (1)3.080 (4)168 (4)
N5—H5B···O11iii0.84 (1)2.23 (2)3.041 (4)163 (3)
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z+1; (iii) x1, y+1, z.
(II) 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium 2-[(2-carboxyphenyl)disulfanyl]benzoate top
Crystal data top
C9H8Cl2N5+·C14H9O4S2Z = 2
Mr = 562.44F(000) = 576
Triclinic, P1Dx = 1.560 Mg m3
a = 8.5368 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.3100 (8) ÅCell parameters from 2580 reflections
c = 12.9348 (8) Åθ = 3.9–28.3°
α = 64.689 (6)°µ = 0.49 mm1
β = 86.474 (5)°T = 294 K
γ = 77.230 (5)°Prism, colourless
V = 1197.56 (14) Å30.44 × 0.26 × 0.16 mm
Data collection top
Oxford Diffraction Gemini CCD S Ultra
diffractometer
3784 reflections with I > 2σ(I)
ω scans, thick slicesRint = 0.028
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
θmax = 28.8°, θmin = 3.4°
Tmin = 0.82, Tmax = 0.90h = 1110
10448 measured reflectionsk = 1616
5165 independent reflectionsl = 1615
Refinement top
Refinement on F28 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) = 0.118 w = 1/[σ2(Fo2) + (0.0463P)2 + 0.5271P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
5165 reflectionsΔρmax = 0.69 e Å3
343 parametersΔρmin = 0.40 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
S110.73570 (9)1.26649 (6)0.70633 (6)0.04003 (18)
O110.7797 (2)1.47988 (16)0.70498 (17)0.0447 (5)
O210.6634 (3)1.56226 (16)0.82134 (18)0.0480 (5)
H21O0.687 (4)1.627 (2)0.770 (2)0.072*
C110.6616 (3)1.2586 (2)0.8408 (2)0.0319 (5)
C210.6106 (3)1.1548 (2)0.9203 (2)0.0410 (6)
H210.61801.08730.90390.049*
C310.5496 (3)1.1506 (3)1.0225 (3)0.0478 (7)
H310.51631.08041.07430.057*
C410.5373 (4)1.2488 (3)1.0488 (3)0.0504 (7)
H410.49421.24601.11750.061*
C510.5891 (3)1.3514 (2)0.9729 (2)0.0421 (6)
H510.58241.41740.99150.050*
C610.6516 (3)1.3585 (2)0.8688 (2)0.0317 (5)
C710.7057 (3)1.4711 (2)0.7898 (2)0.0341 (6)
S120.65073 (8)1.13349 (6)0.68552 (6)0.03733 (18)
O120.5271 (2)0.97209 (15)0.65169 (16)0.0404 (4)
O220.65550 (19)0.79103 (14)0.65987 (15)0.0341 (4)
C120.8020 (3)0.9961 (2)0.7504 (2)0.0305 (5)
C220.9368 (3)0.9932 (3)0.8073 (3)0.0438 (7)
H220.95001.06460.81070.053*
C321.0506 (3)0.8864 (3)0.8584 (3)0.0525 (8)
H321.14060.88650.89530.063*
C421.0333 (3)0.7795 (3)0.8559 (3)0.0497 (7)
H421.10990.70700.89190.060*
C520.9007 (3)0.7810 (2)0.7991 (2)0.0388 (6)
H520.88900.70850.79720.047*
C620.7838 (3)0.8881 (2)0.7445 (2)0.0277 (5)
C720.6447 (3)0.8848 (2)0.6814 (2)0.0281 (5)
Cl10.13956 (11)0.45741 (7)0.85919 (7)0.0587 (2)
Cl20.14555 (11)0.18571 (7)0.90091 (8)0.0671 (3)
N10.3716 (2)0.65097 (18)0.63653 (19)0.0358 (5)
N20.3601 (2)0.76963 (19)0.61448 (19)0.0345 (5)
H20.4487 (19)0.782 (2)0.628 (2)0.041*
N30.2263 (3)0.96928 (19)0.5602 (2)0.0396 (5)
H3A0.1440 (19)1.0264 (18)0.541 (2)0.048*
H3B0.3078 (19)0.990 (2)0.573 (2)0.048*
N40.0856 (2)0.82868 (17)0.56417 (18)0.0309 (5)
N50.0450 (2)0.6778 (2)0.5876 (2)0.0414 (6)
H5A0.1348 (19)0.7259 (18)0.581 (2)0.050*
H5B0.050 (3)0.6039 (10)0.614 (2)0.050*
C10.2237 (3)0.8559 (2)0.5791 (2)0.0293 (5)
C20.0902 (3)0.7111 (2)0.5919 (2)0.0308 (5)
C30.2401 (3)0.6199 (2)0.6266 (2)0.0320 (5)
C40.2482 (3)0.4890 (2)0.6501 (2)0.0354 (6)
C50.2010 (3)0.4083 (2)0.7538 (2)0.0383 (6)
C60.2043 (3)0.2872 (2)0.7723 (3)0.0427 (7)
C70.2552 (3)0.2480 (3)0.6893 (3)0.0488 (7)
H70.25670.16750.70210.059*
C80.3044 (3)0.3279 (3)0.5863 (3)0.0478 (7)
H80.34100.30030.53070.057*
C90.2996 (3)0.4478 (2)0.5655 (2)0.0411 (6)
H90.33050.50160.49540.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S110.0611 (4)0.0278 (3)0.0380 (4)0.0185 (3)0.0065 (3)0.0166 (3)
O110.0587 (12)0.0332 (10)0.0514 (12)0.0235 (9)0.0149 (10)0.0216 (9)
O210.0724 (14)0.0251 (9)0.0529 (13)0.0144 (9)0.0075 (10)0.0213 (9)
C110.0319 (13)0.0269 (12)0.0376 (14)0.0085 (10)0.0014 (10)0.0131 (11)
C210.0517 (16)0.0305 (13)0.0452 (17)0.0177 (12)0.0016 (13)0.0161 (12)
C310.0542 (17)0.0415 (16)0.0474 (18)0.0243 (14)0.0107 (14)0.0131 (14)
C410.0549 (18)0.0504 (17)0.0465 (18)0.0147 (14)0.0197 (14)0.0219 (14)
C510.0468 (16)0.0316 (13)0.0503 (18)0.0046 (12)0.0056 (13)0.0221 (13)
C610.0310 (13)0.0231 (12)0.0411 (15)0.0039 (10)0.0018 (11)0.0142 (11)
C710.0355 (13)0.0277 (12)0.0428 (16)0.0060 (11)0.0040 (11)0.0182 (11)
S120.0473 (4)0.0266 (3)0.0427 (4)0.0061 (3)0.0077 (3)0.0187 (3)
O120.0336 (10)0.0332 (9)0.0603 (13)0.0015 (8)0.0101 (8)0.0266 (9)
O220.0345 (9)0.0251 (8)0.0494 (11)0.0093 (7)0.0026 (8)0.0201 (8)
C120.0364 (13)0.0277 (12)0.0309 (13)0.0095 (10)0.0022 (10)0.0147 (10)
C220.0452 (16)0.0408 (15)0.0570 (18)0.0130 (13)0.0063 (13)0.0290 (14)
C320.0419 (16)0.0614 (19)0.063 (2)0.0055 (15)0.0169 (14)0.0345 (17)
C420.0446 (16)0.0472 (16)0.0564 (19)0.0050 (13)0.0179 (14)0.0256 (15)
C520.0450 (15)0.0320 (13)0.0434 (16)0.0056 (12)0.0068 (12)0.0200 (12)
C620.0290 (12)0.0268 (12)0.0302 (13)0.0092 (10)0.0030 (10)0.0135 (10)
C720.0297 (12)0.0257 (12)0.0319 (13)0.0116 (10)0.0043 (10)0.0126 (10)
Cl10.0803 (6)0.0491 (4)0.0488 (5)0.0151 (4)0.0096 (4)0.0232 (4)
Cl20.0863 (6)0.0453 (4)0.0607 (5)0.0300 (4)0.0017 (4)0.0066 (4)
N10.0291 (11)0.0292 (11)0.0498 (14)0.0056 (9)0.0029 (9)0.0172 (10)
N20.0249 (11)0.0309 (11)0.0507 (14)0.0093 (9)0.0037 (9)0.0178 (10)
N30.0329 (12)0.0264 (11)0.0597 (15)0.0123 (9)0.0014 (11)0.0152 (11)
N40.0248 (10)0.0252 (10)0.0409 (12)0.0085 (8)0.0008 (8)0.0108 (9)
N50.0275 (11)0.0285 (11)0.0656 (16)0.0095 (9)0.0035 (11)0.0153 (12)
C10.0258 (12)0.0307 (12)0.0313 (13)0.0088 (10)0.0039 (10)0.0124 (10)
C20.0273 (12)0.0298 (12)0.0354 (14)0.0090 (10)0.0010 (10)0.0126 (11)
C30.0287 (12)0.0261 (12)0.0399 (15)0.0060 (10)0.0012 (10)0.0124 (11)
C40.0278 (13)0.0278 (12)0.0487 (16)0.0040 (10)0.0046 (11)0.0146 (12)
C50.0331 (13)0.0354 (14)0.0450 (16)0.0057 (11)0.0017 (11)0.0163 (12)
C60.0377 (14)0.0283 (13)0.0555 (18)0.0089 (11)0.0067 (13)0.0096 (13)
C70.0481 (17)0.0341 (15)0.067 (2)0.0054 (13)0.0061 (15)0.0248 (15)
C80.0462 (16)0.0458 (16)0.059 (2)0.0044 (13)0.0020 (14)0.0312 (15)
C90.0389 (15)0.0336 (14)0.0475 (17)0.0066 (11)0.0056 (12)0.0152 (12)
Geometric parameters (Å, º) top
S11—C111.784 (3)C52—H520.9300
S11—S122.0506 (9)C62—C721.498 (3)
O11—C711.207 (3)Cl1—C51.725 (3)
O21—C711.323 (3)Cl2—C61.726 (3)
O21—H21O0.849 (10)N1—C31.294 (3)
C11—C211.396 (3)N1—N21.345 (3)
C11—C611.407 (3)N2—C11.341 (3)
C21—C311.375 (4)N2—H20.847 (10)
C21—H210.9300N3—C11.315 (3)
C31—C411.371 (4)N3—H3A0.838 (9)
C31—H310.9300N3—H3B0.839 (10)
C41—C511.374 (4)N4—C21.326 (3)
C41—H410.9300N4—C11.341 (3)
C51—C611.392 (4)N5—C21.319 (3)
C51—H510.9300N5—H5A0.841 (10)
C61—C711.481 (3)N5—H5B0.833 (9)
S12—C121.785 (2)C2—C31.450 (3)
O12—C721.236 (3)C3—C41.492 (3)
O22—C721.283 (3)C4—C51.387 (4)
C12—C221.389 (3)C4—C91.401 (4)
C12—C621.407 (3)C5—C61.399 (4)
C22—C321.371 (4)C6—C71.366 (4)
C22—H220.9300C7—C81.383 (4)
C32—C421.369 (4)C7—H70.9300
C32—H320.9300C8—C91.374 (4)
C42—C521.380 (4)C8—H80.9300
C42—H420.9300C9—H90.9300
C52—C621.393 (3)
C11—S11—S12103.92 (8)O12—C72—O22123.3 (2)
C71—O21—H21O109 (2)O12—C72—C62119.1 (2)
C21—C11—C61118.2 (2)O22—C72—C62117.6 (2)
C21—C11—S11121.4 (2)C3—N1—N2116.6 (2)
C61—C11—S11120.40 (18)C1—N2—N1123.87 (19)
C31—C21—C11121.1 (3)C1—N2—H2124.3 (19)
C31—C21—H21119.5N1—N2—H2111.8 (19)
C11—C21—H21119.5C1—N3—H3A123.2 (17)
C41—C31—C21120.6 (3)C1—N3—H3B123.4 (17)
C41—C31—H31119.7H3A—N3—H3B113 (2)
C21—C31—H31119.7C2—N4—C1116.2 (2)
C31—C41—C51119.5 (3)C2—N5—H5A121.3 (18)
C31—C41—H41120.3C2—N5—H5B121.4 (18)
C51—C41—H41120.3H5A—N5—H5B114 (2)
C41—C51—C61121.3 (3)N3—C1—N4119.7 (2)
C41—C51—H51119.4N3—C1—N2118.7 (2)
C61—C51—H51119.4N4—C1—N2121.5 (2)
C51—C61—C11119.3 (2)N5—C2—N4118.6 (2)
C51—C61—C71119.2 (2)N5—C2—C3120.1 (2)
C11—C61—C71121.5 (2)N4—C2—C3121.2 (2)
O11—C71—O21123.2 (2)N1—C3—C2120.3 (2)
O11—C71—C61123.9 (2)N1—C3—C4118.2 (2)
O21—C71—C61112.9 (2)C2—C3—C4121.5 (2)
C12—S12—S11105.17 (8)C5—C4—C9119.4 (2)
C22—C12—C62119.2 (2)C5—C4—C3120.6 (2)
C22—C12—S12121.56 (19)C9—C4—C3119.9 (2)
C62—C12—S12119.25 (18)C4—C5—C6119.6 (3)
C32—C22—C12120.9 (2)C4—C5—Cl1119.9 (2)
C32—C22—H22119.6C6—C5—Cl1120.6 (2)
C12—C22—H22119.6C7—C6—C5120.4 (3)
C42—C32—C22120.9 (3)C7—C6—Cl2119.5 (2)
C42—C32—H32119.6C5—C6—Cl2120.1 (2)
C22—C32—H32119.6C6—C7—C8120.1 (3)
C32—C42—C52119.0 (3)C6—C7—H7119.9
C32—C42—H42120.5C8—C7—H7119.9
C52—C42—H42120.5C9—C8—C7120.4 (3)
C42—C52—C62121.8 (2)C9—C8—H8119.8
C42—C52—H52119.1C7—C8—H8119.8
C62—C52—H52119.1C8—C9—C4120.0 (3)
C52—C62—C12118.2 (2)C8—C9—H9120.0
C52—C62—C72119.4 (2)C4—C9—H9120.0
C12—C62—C72122.4 (2)
S12—S11—C11—C2119.1 (2)C12—C62—C72—O22165.4 (2)
S12—S11—C11—C61160.19 (18)C3—N1—N2—C12.8 (4)
C61—C11—C21—C311.1 (4)C2—N4—C1—N3175.8 (2)
S11—C11—C21—C31178.2 (2)C2—N4—C1—N23.3 (4)
C11—C21—C31—C410.0 (4)N1—N2—C1—N3179.9 (2)
C21—C31—C41—C511.1 (5)N1—N2—C1—N40.8 (4)
C31—C41—C51—C611.1 (4)C1—N4—C2—N5174.6 (2)
C41—C51—C61—C110.1 (4)C1—N4—C2—C35.2 (4)
C41—C51—C61—C71179.9 (2)N2—N1—C3—C20.8 (4)
C21—C11—C61—C511.1 (4)N2—N1—C3—C4179.8 (2)
S11—C11—C61—C51178.21 (19)N5—C2—C3—N1176.5 (3)
C21—C11—C61—C71179.0 (2)N4—C2—C3—N13.4 (4)
S11—C11—C61—C711.7 (3)N5—C2—C3—C44.5 (4)
C51—C61—C71—O11170.2 (3)N4—C2—C3—C4175.7 (2)
C11—C61—C71—O119.9 (4)N1—C3—C4—C5100.9 (3)
C51—C61—C71—O2110.3 (3)C2—C3—C4—C580.1 (3)
C11—C61—C71—O21169.6 (2)N1—C3—C4—C981.0 (3)
S11—S12—C12—C224.2 (2)C2—C3—C4—C998.1 (3)
S11—S12—C12—C62176.30 (17)C9—C4—C5—C60.4 (4)
C62—C12—C22—C320.7 (4)C3—C4—C5—C6177.8 (2)
S12—C12—C22—C32178.8 (2)C9—C4—C5—Cl1179.27 (19)
C12—C22—C32—C420.8 (5)C3—C4—C5—Cl12.6 (3)
C22—C32—C42—C521.2 (5)C4—C5—C6—C70.6 (4)
C32—C42—C52—C620.1 (5)Cl1—C5—C6—C7179.1 (2)
C42—C52—C62—C121.3 (4)C4—C5—C6—Cl2179.89 (19)
C42—C52—C62—C72178.4 (3)Cl1—C5—C6—Cl20.4 (3)
C22—C12—C62—C521.7 (4)C5—C6—C7—C80.2 (4)
S12—C12—C62—C52177.84 (19)Cl2—C6—C7—C8179.3 (2)
C22—C12—C62—C72178.0 (2)C6—C7—C8—C91.3 (4)
S12—C12—C62—C722.5 (3)C7—C8—C9—C41.5 (4)
C52—C62—C72—O12166.6 (2)C5—C4—C9—C80.6 (4)
C12—C62—C72—O1213.8 (3)C3—C4—C9—C8178.8 (2)
C52—C62—C72—O2214.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O21—H21O···O22i0.85 (1)1.88 (2)2.683 (2)158 (3)
C21—H21···S120.932.643.150 (3)115
C22—H22···S110.932.603.152 (3)118
N2—H2···O220.85 (1)1.87 (1)2.717 (2)173 (3)
N3—H3A···N4ii0.84 (1)2.36 (1)3.168 (3)161 (3)
N3—H3B···O120.84 (1)2.11 (1)2.906 (3)158 (2)
N5—H5A···O22iii0.84 (1)2.18 (2)2.932 (3)149 (3)
N5—H5B···O11iv0.83 (1)2.25 (2)2.941 (3)140 (2)
Symmetry codes: (i) x, y+1, z; (ii) x, y+2, z+1; (iii) x1, y, z; (iv) x1, y1, z.
Selected geometric parameters (Å, °) top
HB denotes hydrogen bond.
(I)(II)Comment
O11—C711.222 (4)1.207 (3)Double bond
O21—C711.331 (4)1.323 (3)HB donor
O12—C721.245 (4)1.236 (3)Double HB acceptor
O22—C721.270 (4)1.283 (3)Single HB acceptor
C12—S12—S11—C11-83.7 (2)-89.4 (2)
N1—C3—C4—C571.0 (4)100.9 (3)
Hydrogen-bond geometry (Å, °) in (I) top
CodeD—H···AD—HH···AD···AD—H···A
#1aC21—H21···S120.932.643.181 (4)118
#2aC22—H22···S110.932.593.146 (4)119
#3aO21—H21O···O22i0.849 (10)1.779 (16)2.599 (3)162 (4)
#4aN2—H2···O220.847 (10)1.845 (12)2.686 (3)172 (4)
#5aN3—H3B···O120.844 (10)1.976 (11)2.811 (4)170 (3)
#6aN5—H5A···N4ii0.838 (10)2.251 (13)3.079 (4)169 (4)
#7aN5—H5B···O11iii0.840 (10)2.232 (15)3.042 (4)162 (3)
#8aN3—H3A···O1WA0.842 (10)2.219 (13)3.055 (5)172 (4)
#8a'N3—H3A···O1WB0.842 (10)1.81 (2)2.606 (9)158 (4)
Symmetry codes: (i) x, y-1, z; (ii) -x, -y+1, -z+1; (iii) x-1, y+1, z.
C—X···Cg (X = O or Cl) contacts (Å) in (I) top
Ring codes are as shown in Fig. 1.
LabelC—X···CgX···Cg(X···Cg)perp
#9aC5—Cl2···Cg1iv3.804 (2)3.751
#10aC6—Cl1···Cg2v3.813 (2)3.349
#11aC71—O11···Cg4vi3.474 (3)3.337
#12aC72—O21···Cg3vii3.973 (3)3.444
Symmetry codes: (iv) x, y+1, z; (v) -x+1, -y+1, -z; (vi) x+1, y-1, z; (vii) -x+1, -y+1, -z+1.
Hydrogen-bond geometry (Å, °) in (II). top
CodeD—H···AD—HH···AD···AD—H···A
#1bC21—H21···S120.932.643.150 (3)115
#2bC22—H22···S110.932.603.152 (3)118
#3bO21—H21O···O22i0.849 (10)1.877 (16)2.683 (2)158 (3)
#4bN2—H2···O220.847 (10)1.874 (11)2.717 (2)173 (3)
#5bN3—H3B···O120.839 (10)2.111 (13)2.906 (3)158 (2)
#6bN3—H3A···N4ii0.838 (9)2.364 (13)3.168 (3)161 (3)
#7bN5—H5B···O11iii0.833 (9)2.252 (19)2.941 (3)140 (2)
#8bN5—H5A···O22iv0.841 (10)2.176 (18)2.932 (3)149 (3)
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+2, -z+1; (iii) x-1, y-1, z; (iv) x-1, y, z.
C—Cl···Cg contacts (Å) in (II) top
Ring codes are as shown in Fig. 1.
LabelC—Cl···CgCl···Cg(Cl···Cg)perp
#9bC6—Cl2iv···Cg23.581 (2)3.299
Symmetry code: (iv) -x+1, -y+1, -z+2.
 

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