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The structure of the title compound, C32H22Cl4N6S4, (I), comprises two unique mol­ecules that separately associate via a three-centre N—H...N/S interaction to form two linear one-dimensional hydrogen-bonded chains. The dihedral angles between the two phenyl rings and the pyrimidine ring for each mol­ecule are 84.6 (1) and 87.8 (1)°, and 83.9 (1) and 80.1 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680001761X/na6000sup1.cif
Contains datablocks I, default

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680001761X/na6000Isup2.hkl
Contains datablock I

CCDC reference: 155857

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.056
  • wR factor = 0.148
  • Data-to-parameter ratio = 17.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 7363 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 7809 Completeness (_total/calc) 94.29% Alert C: < 95% complete PLAT_420 Alert C D-H without acceptor N(21A) - H(22A) ? PLAT_420 Alert C D-H without acceptor N(21B) - H(22B) ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check

Comment top

NO COMMENT

Experimental top

Crystals of (I) were obtained from Spa Contract Synthesis.

Refinement top

All H atoms were included in the refinement, at calculated positions, as riding models with C—H set to 0.95 Å (Ar—H), except for the amine H atoms which were located on difference syntheses and both positional and displacement parameters refined.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

2-Amino-4,6-bis(4-chlorophenylthio)pyrimidine top
Crystal data top
C32H22Cl4N6S4F(000) = 1552
Mr = 760.60Dx = 1.487 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 28.4777 (13) ÅCell parameters from 12187 reflections
b = 8.6020 (3) Åθ = 1.0–30.5°
c = 14.2055 (5) ŵ = 0.63 mm1
β = 102.5620 (13)°T = 150 K
V = 3396.5 (2) Å3Prism, colourless
Z = 40.15 × 0.15 × 0.10 mm
Data collection top
Enraf Nonius KappaCCD area-detector
diffractometer
7363 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode4286 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.080
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 1.5°
ϕ and ω scansh = 3637
Absorption correction: multi-scan
SORTAV (Blessing, 1995)
k = 1110
Tmin = 0.912, Tmax = 0.940l = 1817
20121 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.148 w = 1/[σ2(Fo2) + (0.0703P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
7363 reflectionsΔρmax = 0.33 e Å3
432 parametersΔρmin = 0.39 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0046 (6)
Crystal data top
C32H22Cl4N6S4V = 3396.5 (2) Å3
Mr = 760.60Z = 4
Monoclinic, P21/cMo Kα radiation
a = 28.4777 (13) ŵ = 0.63 mm1
b = 8.6020 (3) ÅT = 150 K
c = 14.2055 (5) Å0.15 × 0.15 × 0.10 mm
β = 102.5620 (13)°
Data collection top
Enraf Nonius KappaCCD area-detector
diffractometer
7363 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1995)
4286 reflections with I > 2σ(I)
Tmin = 0.912, Tmax = 0.940Rint = 0.080
20121 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 0.97Δρmax = 0.33 e Å3
7363 reflectionsΔρmin = 0.39 e Å3
432 parameters
Special details top

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Geometry. Mean plane data ex SHELXL97 ###########################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 1.3912 (0.0419) x + 8.5813 (0.0009) y - 0.5311 (0.0191) z = 0.7704 (0.0146)

* -0.0018 (0.0022) C8A * 0.0025 (0.0024) C9A * -0.0004 (0.0025) C10A * -0.0026 (0.0025) C11A * 0.0033 (0.0025) C12A * -0.0011 (0.0023) C13A

Rms deviation of fitted atoms = 0.0022

26.4157 (0.0128) x - 0.5748 (0.0101) y - 7.9624 (0.0140) z = 7.1447 (0.0154)

Angle to previous plane (with approximate e.s.d.) = 84.61 (0.11)

* -0.0017 (0.0019) N1A * -0.0013 (0.0021) C2A * 0.0036 (0.0020) N3A * -0.0031 (0.0021) C4A * 0.0002 (0.0021) C5A * 0.0023 (0.0020) C6A

Rms deviation of fitted atoms = 0.0023

- 2.0118 (0.0420) x + 8.3084 (0.0032) y - 3.2374 (0.0205) z = 4.2869 (0.0157)

Angle to previous plane (with approximate e.s.d.) = 87.80 (0.11)

* 0.0010 (0.0023) C15A * 0.0009 (0.0025) C16A * -0.0040 (0.0026) C17A * 0.0052 (0.0027) C18A * -0.0032 (0.0025) C19A * 0.0001 (0.0023) C20A

Rms deviation of fitted atoms = 0.0030

6.0898 (0.0397) x + 8.3974 (0.0027) y - 1.1546 (0.0187) z = 5.4068 (0.0123)

Angle to previous plane (with approximate e.s.d.) = 20.50 (0.07)

* -0.0117 (0.0021) C8B * 0.0024 (0.0022) C9B * 0.0091 (0.0024) C10B * -0.0113 (0.0025) C11B * 0.0017 (0.0024) C12B * 0.0098 (0.0023) C13B

Rms deviation of fitted atoms = 0.0087

- 26.2289 (0.0129) x + 0.9118 (0.0099) y + 8.0422 (0.0137) z = 3.1829 (0.0112)

Angle to previous plane (with approximate e.s.d.) = 83.87 (0.10)

* -0.0036 (0.0019) N1B * 0.0057 (0.0020) C2B * -0.0006 (0.0019) N3B * -0.0061 (0.0020) C4B * 0.0076 (0.0020) C5B * -0.0030 (0.0020) C6B

Rms deviation of fitted atoms = 0.0050

10.0127 (0.0400) x + 7.9553 (0.0047) y + 0.9270 (0.0200) z = 11.5050 (0.0120)

Angle to previous plane (with approximate e.s.d.) = 80.13 (0.10)

* -0.0087 (0.0022) C15B * 0.0038 (0.0024) C16B * -0.0002 (0.0026) C17B * 0.0014 (0.0026) C18B * -0.0063 (0.0026) C19B * 0.0100 (0.0025) C20B

Rms deviation of fitted atoms = 0.0062

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.47036 (9)0.6658 (3)0.61528 (16)0.0261 (6)
C2A0.48381 (11)0.5371 (3)0.66914 (19)0.0258 (7)
N21A0.51080 (11)0.5590 (4)0.75831 (19)0.0342 (7)
H21A0.5147 (12)0.644 (4)0.780 (2)0.043 (12)*
H22A0.5146 (14)0.483 (5)0.793 (3)0.062 (14)*
N3A0.47261 (9)0.3895 (3)0.64203 (16)0.0286 (6)
C4A0.44511 (11)0.3712 (3)0.55295 (19)0.0267 (7)
C5A0.42929 (11)0.4931 (3)0.49126 (19)0.0257 (7)
H5A0.41000.47770.42840.032*
C6A0.44332 (10)0.6389 (3)0.52701 (19)0.0240 (7)
S7A0.43223 (4)0.17497 (9)0.52689 (6)0.0444 (3)
C8A0.39055 (12)0.1785 (3)0.4140 (2)0.0312 (8)
C9A0.34204 (13)0.1709 (4)0.4101 (2)0.0435 (9)
H9A0.33050.17320.46800.054*
C10A0.30979 (13)0.1599 (4)0.3222 (2)0.0482 (10)
H10A0.27620.15420.31910.060*
C11A0.32744 (13)0.1574 (4)0.2393 (2)0.0371 (8)
Cl1A0.28745 (4)0.13975 (14)0.12823 (6)0.0620 (3)
C12A0.37537 (13)0.1660 (4)0.2418 (2)0.0420 (9)
H12A0.38670.16500.18360.052*
C13A0.40742 (12)0.1761 (4)0.3299 (2)0.0387 (8)
H13A0.44100.18140.33260.048*
S14A0.42727 (3)0.81190 (9)0.46199 (5)0.0345 (2)
C15A0.38524 (11)0.7488 (3)0.35790 (19)0.0283 (7)
C16A0.33700 (13)0.7374 (4)0.3585 (2)0.0417 (9)
H16A0.32630.75770.41620.052*
C17A0.30409 (13)0.6964 (4)0.2752 (2)0.0479 (10)
H17A0.27090.68730.27540.060*
C18A0.32027 (13)0.6690 (4)0.1920 (2)0.0417 (9)
Cl2A0.27902 (4)0.62041 (16)0.08715 (6)0.0754 (4)
C19A0.36806 (13)0.6789 (4)0.1905 (2)0.0452 (9)
H19A0.37860.65810.13280.057*
C20A0.40071 (12)0.7196 (4)0.2736 (2)0.0365 (8)
H20A0.43390.72770.27300.046*
N1B0.03378 (9)1.1381 (3)0.37647 (16)0.0262 (6)
C2B0.01437 (10)1.0095 (3)0.32893 (19)0.0247 (7)
N21B0.01250 (10)1.0303 (4)0.23939 (18)0.0329 (7)
H21B0.0137 (11)1.117 (4)0.215 (2)0.024 (9)*
H22B0.0223 (12)0.951 (4)0.204 (2)0.045 (11)*
N3B0.01966 (9)0.8625 (3)0.36203 (15)0.0252 (6)
C4B0.04671 (11)0.8455 (3)0.45152 (19)0.0244 (7)
C5B0.06778 (10)0.9680 (3)0.50803 (19)0.0246 (7)
H5B0.08620.95380.57170.031*
C6B0.06011 (10)1.1132 (3)0.46523 (19)0.0236 (7)
S7B0.05197 (3)0.65027 (9)0.48769 (5)0.0347 (2)
C8B0.09758 (11)0.6535 (3)0.59522 (19)0.0270 (7)
C9B0.08499 (12)0.6764 (4)0.6830 (2)0.0341 (8)
H9B0.05270.70080.68530.043*
C10B0.11985 (12)0.6636 (4)0.7677 (2)0.0394 (9)
H10B0.11170.68000.82830.049*
C11B0.16589 (12)0.6271 (4)0.7630 (2)0.0393 (9)
Cl1B0.20838 (4)0.60209 (15)0.87035 (6)0.0688 (4)
C12B0.17931 (12)0.6070 (4)0.6764 (2)0.0415 (9)
H12B0.21170.58370.67470.052*
C13B0.14481 (12)0.6214 (4)0.5921 (2)0.0357 (8)
H13B0.15350.60920.53170.045*
S14B0.08396 (3)1.28593 (9)0.52263 (5)0.0315 (2)
C15B0.12233 (11)1.2177 (3)0.63009 (19)0.0271 (7)
C16B0.10738 (12)1.2281 (4)0.7163 (2)0.0368 (8)
H16B0.07641.26840.71720.046*
C17B0.13721 (13)1.1802 (4)0.8005 (2)0.0444 (9)
H17B0.12681.18590.85960.055*
C18B0.18226 (13)1.1239 (4)0.7992 (2)0.0410 (9)
Cl2B0.21979 (4)1.06277 (15)0.90598 (6)0.0721 (4)
C19B0.19785 (13)1.1132 (4)0.7142 (2)0.0472 (10)
H19B0.22881.07220.71370.059*
C20B0.16784 (12)1.1628 (4)0.6297 (2)0.0404 (9)
H20B0.17861.15920.57090.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0308 (15)0.0210 (13)0.0240 (12)0.0006 (11)0.0003 (11)0.0016 (11)
C2A0.0291 (18)0.0262 (17)0.0202 (15)0.0014 (14)0.0016 (13)0.0011 (13)
N21A0.046 (2)0.0242 (17)0.0257 (15)0.0005 (14)0.0070 (12)0.0054 (14)
N3A0.0373 (17)0.0226 (14)0.0227 (13)0.0013 (12)0.0003 (11)0.0012 (11)
C4A0.0329 (19)0.0250 (17)0.0200 (14)0.0004 (14)0.0010 (13)0.0021 (13)
C5A0.0330 (18)0.0194 (16)0.0212 (14)0.0006 (14)0.0021 (12)0.0010 (12)
C6A0.0261 (17)0.0224 (16)0.0228 (15)0.0001 (13)0.0035 (12)0.0006 (13)
S7A0.0715 (7)0.0186 (4)0.0304 (4)0.0050 (4)0.0165 (4)0.0014 (3)
C8A0.047 (2)0.0161 (15)0.0245 (16)0.0027 (14)0.0040 (14)0.0004 (13)
C9A0.052 (3)0.049 (2)0.0297 (18)0.0034 (19)0.0093 (16)0.0045 (16)
C10A0.035 (2)0.068 (3)0.039 (2)0.0052 (19)0.0033 (16)0.0007 (19)
C11A0.043 (2)0.038 (2)0.0265 (16)0.0054 (17)0.0012 (15)0.0021 (15)
Cl1A0.0496 (6)0.0947 (9)0.0329 (5)0.0096 (6)0.0103 (4)0.0044 (5)
C12A0.039 (2)0.061 (2)0.0259 (17)0.0015 (18)0.0059 (15)0.0006 (17)
C13A0.035 (2)0.044 (2)0.0345 (18)0.0056 (16)0.0016 (15)0.0029 (16)
S14A0.0505 (6)0.0179 (4)0.0285 (4)0.0005 (4)0.0057 (4)0.0001 (3)
C15A0.038 (2)0.0180 (16)0.0250 (15)0.0035 (14)0.0014 (13)0.0007 (13)
C16A0.045 (2)0.050 (2)0.0295 (17)0.0074 (18)0.0063 (15)0.0075 (16)
C17A0.031 (2)0.073 (3)0.0369 (19)0.0007 (19)0.0025 (16)0.0074 (19)
C18A0.041 (2)0.053 (2)0.0270 (17)0.0079 (18)0.0033 (15)0.0001 (16)
Cl2A0.0587 (7)0.1283 (11)0.0317 (5)0.0276 (7)0.0066 (5)0.0079 (6)
C19A0.049 (2)0.059 (2)0.0282 (17)0.0121 (19)0.0084 (16)0.0060 (17)
C20A0.033 (2)0.042 (2)0.0325 (18)0.0054 (16)0.0041 (15)0.0023 (15)
N1B0.0310 (15)0.0214 (14)0.0246 (13)0.0002 (11)0.0028 (11)0.0003 (11)
C2B0.0274 (18)0.0256 (17)0.0202 (14)0.0026 (14)0.0031 (12)0.0014 (13)
N21B0.0448 (19)0.0252 (16)0.0234 (14)0.0018 (14)0.0043 (12)0.0030 (14)
N3B0.0299 (15)0.0224 (14)0.0216 (12)0.0025 (11)0.0015 (10)0.0001 (10)
C4B0.0296 (18)0.0229 (16)0.0206 (14)0.0013 (13)0.0048 (12)0.0035 (12)
C5B0.0319 (18)0.0211 (16)0.0185 (14)0.0001 (13)0.0004 (12)0.0004 (12)
C6B0.0283 (18)0.0211 (16)0.0213 (14)0.0001 (13)0.0053 (12)0.0020 (12)
S7B0.0512 (6)0.0180 (4)0.0274 (4)0.0013 (4)0.0077 (4)0.0012 (3)
C8B0.040 (2)0.0146 (15)0.0225 (15)0.0003 (14)0.0027 (13)0.0003 (12)
C9B0.0317 (19)0.038 (2)0.0323 (17)0.0049 (15)0.0051 (14)0.0004 (15)
C10B0.039 (2)0.053 (2)0.0256 (16)0.0032 (17)0.0073 (15)0.0017 (16)
C11B0.035 (2)0.048 (2)0.0301 (17)0.0010 (17)0.0027 (15)0.0065 (16)
Cl1B0.0476 (7)0.1083 (10)0.0398 (5)0.0003 (6)0.0139 (4)0.0095 (6)
C12B0.028 (2)0.055 (2)0.0405 (19)0.0004 (17)0.0048 (15)0.0015 (18)
C13B0.042 (2)0.036 (2)0.0293 (17)0.0004 (16)0.0073 (15)0.0032 (15)
S14B0.0436 (5)0.0179 (4)0.0287 (4)0.0022 (4)0.0018 (3)0.0005 (3)
C15B0.0331 (19)0.0221 (16)0.0241 (15)0.0052 (14)0.0023 (13)0.0046 (13)
C16B0.035 (2)0.042 (2)0.0330 (18)0.0018 (16)0.0078 (15)0.0026 (16)
C17B0.048 (2)0.059 (2)0.0257 (17)0.0020 (19)0.0073 (16)0.0041 (17)
C18B0.041 (2)0.050 (2)0.0274 (17)0.0030 (18)0.0009 (15)0.0042 (16)
Cl2B0.0602 (7)0.1112 (10)0.0360 (5)0.0046 (7)0.0095 (5)0.0163 (6)
C19B0.040 (2)0.067 (3)0.0343 (19)0.0101 (19)0.0057 (16)0.0028 (18)
C20B0.043 (2)0.053 (2)0.0258 (16)0.0011 (18)0.0098 (15)0.0016 (16)
Geometric parameters (Å, º) top
N1A—C6A1.341 (3)N1B—C6B1.337 (3)
N1A—C2A1.353 (3)N1B—C2B1.350 (3)
C2A—N21A1.344 (4)C2B—N3B1.346 (4)
C2A—N3A1.345 (4)C2B—N21B1.346 (3)
N21A—H21A0.79 (4)N21B—H21B0.82 (3)
N21A—H22A0.81 (4)N21B—H22B0.86 (3)
N3A—C4A1.345 (3)N3B—C4B1.343 (3)
C4A—C5A1.378 (4)C4B—C5B1.380 (4)
C4A—S7A1.750 (3)C4B—S7B1.753 (3)
C5A—C6A1.380 (4)C5B—C6B1.385 (4)
C5A—H5A0.9500C5B—H5B0.9500
C6A—S14A1.758 (3)C6B—S14B1.759 (3)
S7A—C8A1.776 (3)S7B—C8B1.777 (3)
C8A—C9A1.372 (5)C8B—C9B1.385 (4)
C8A—C13A1.382 (4)C8B—C13B1.383 (4)
C9A—C10A1.383 (4)C9B—C10B1.387 (4)
C9A—H9A0.9500C9B—H9B0.9500
C10A—C11A1.378 (4)C10B—C11B1.364 (5)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.360 (5)C11B—C12B1.375 (4)
C11A—Cl1A1.740 (3)C11B—Cl1B1.742 (3)
C12A—C13A1.382 (4)C12B—C13B1.379 (4)
C12A—H12A0.9500C12B—H12B0.9500
C13A—H13A0.9500C13B—H13B0.9500
S14A—C15A1.773 (3)S14B—C15B1.773 (3)
C15A—C16A1.379 (4)C15B—C20B1.381 (4)
C15A—C20A1.386 (4)C15B—C16B1.385 (4)
C16A—C17A1.386 (4)C16B—C17B1.371 (4)
C16A—H16A0.9500C16B—H16B0.9500
C17A—C18A1.379 (5)C17B—C18B1.375 (5)
C17A—H17A0.9500C17B—H17B0.9500
C18A—C19A1.369 (5)C18B—C19B1.377 (4)
C18A—Cl2A1.735 (3)C18B—Cl2B1.736 (3)
C19A—C20A1.380 (4)C19B—C20B1.382 (4)
C19A—H19A0.9500C19B—H19B0.9500
C20A—H20A0.9500C20B—H20B0.9500
C6A—N1A—C2A115.0 (2)C6B—N1B—C2B115.2 (2)
N21A—C2A—N3A117.0 (3)N3B—C2B—N21B116.9 (3)
N21A—C2A—N1A116.8 (3)N3B—C2B—N1B126.3 (2)
N3A—C2A—N1A126.2 (2)N21B—C2B—N1B116.8 (3)
C2A—N21A—H21A120 (2)C2B—N21B—H21B119 (2)
C2A—N21A—H22A116 (3)C2B—N21B—H22B120 (2)
H21A—N21A—H22A121 (4)H21B—N21B—H22B119 (3)
C4A—N3A—C2A115.7 (2)C4B—N3B—C2B115.5 (2)
N3A—C4A—C5A123.5 (3)N3B—C4B—C5B123.7 (3)
N3A—C4A—S7A111.4 (2)N3B—C4B—S7B112.1 (2)
C5A—C4A—S7A125.1 (2)C5B—C4B—S7B124.2 (2)
C4A—C5A—C6A115.4 (2)C4B—C5B—C6B115.2 (2)
C4A—C5A—H5A122.3C4B—C5B—H5B122.4
C6A—C5A—H5A122.3C6B—C5B—H5B122.4
N1A—C6A—C5A124.2 (3)N1B—C6B—C5B124.1 (3)
N1A—C6A—S14A112.1 (2)N1B—C6B—S14B112.5 (2)
C5A—C6A—S14A123.7 (2)C5B—C6B—S14B123.4 (2)
C4A—S7A—C8A104.04 (13)C4B—S7B—C8B103.69 (13)
C9A—C8A—C13A120.0 (3)C9B—C8B—C13B120.1 (3)
C9A—C8A—S7A120.4 (2)C9B—C8B—S7B119.5 (3)
C13A—C8A—S7A119.4 (3)C13B—C8B—S7B120.2 (2)
C8A—C9A—C10A120.3 (3)C8B—C9B—C10B119.5 (3)
C8A—C9A—H9A119.8C8B—C9B—H9B120.2
C10A—C9A—H9A119.8C10B—C9B—H9B120.2
C11A—C10A—C9A118.6 (3)C11B—C10B—C9B119.4 (3)
C11A—C10A—H10A120.7C11B—C10B—H10B120.3
C9A—C10A—H10A120.7C9B—C10B—H10B120.3
C12A—C11A—C10A121.9 (3)C10B—C11B—C12B122.0 (3)
C12A—C11A—Cl1A118.9 (2)C10B—C11B—Cl1B118.5 (3)
C10A—C11A—Cl1A119.2 (3)C12B—C11B—Cl1B119.5 (3)
C11A—C12A—C13A119.2 (3)C11B—C12B—C13B118.7 (3)
C11A—C12A—H12A120.4C11B—C12B—H12B120.6
C13A—C12A—H12A120.4C13B—C12B—H12B120.6
C12A—C13A—C8A119.9 (3)C12B—C13B—C8B120.3 (3)
C12A—C13A—H13A120.0C12B—C13B—H13B119.9
C8A—C13A—H13A120.0C8B—C13B—H13B119.9
C6A—S14A—C15A103.32 (13)C6B—S14B—C15B102.90 (13)
C16A—C15A—C20A119.8 (3)C20B—C15B—C16B119.7 (3)
C16A—C15A—S14A120.6 (2)C20B—C15B—S14B120.8 (2)
C20A—C15A—S14A119.5 (3)C16B—C15B—S14B119.4 (2)
C15A—C16A—C17A120.1 (3)C17B—C16B—C15B120.1 (3)
C15A—C16A—H16A119.9C17B—C16B—H16B120.0
C17A—C16A—H16A119.9C15B—C16B—H16B120.0
C18A—C17A—C16A119.0 (3)C16B—C17B—C18B119.8 (3)
C18A—C17A—H17A120.5C16B—C17B—H17B120.1
C16A—C17A—H17A120.5C18B—C17B—H17B120.1
C19A—C18A—C17A121.4 (3)C19B—C18B—C17B121.0 (3)
C19A—C18A—Cl2A119.4 (3)C19B—C18B—Cl2B119.4 (3)
C17A—C18A—Cl2A119.1 (3)C17B—C18B—Cl2B119.6 (3)
C18A—C19A—C20A119.3 (3)C18B—C19B—C20B119.0 (3)
C18A—C19A—H19A120.3C18B—C19B—H19B120.5
C20A—C19A—H19A120.3C20B—C19B—H19B120.5
C19A—C20A—C15A120.2 (3)C15B—C20B—C19B120.4 (3)
C19A—C20A—H20A119.9C15B—C20B—H20B119.8
C15A—C20A—H20A119.9C19B—C20B—H20B119.8
C6A—N1A—C2A—N21A179.7 (3)C6B—N1B—C2B—N3B0.8 (4)
C6A—N1A—C2A—N3A0.0 (4)C6B—N1B—C2B—N21B179.8 (3)
N21A—C2A—N3A—C4A179.2 (3)N21B—C2B—N3B—C4B179.9 (3)
N1A—C2A—N3A—C4A0.5 (5)N1B—C2B—N3B—C4B0.6 (4)
C2A—N3A—C4A—C5A0.7 (4)C2B—N3B—C4B—C5B0.7 (4)
C2A—N3A—C4A—S7A179.1 (2)C2B—N3B—C4B—S7B179.4 (2)
N3A—C4A—C5A—C6A0.4 (5)N3B—C4B—C5B—C6B1.4 (4)
S7A—C4A—C5A—C6A179.3 (2)S7B—C4B—C5B—C6B178.7 (2)
C2A—N1A—C6A—C5A0.3 (4)C2B—N1B—C6B—C5B0.1 (4)
C2A—N1A—C6A—S14A179.8 (2)C2B—N1B—C6B—S14B179.8 (2)
C4A—C5A—C6A—N1A0.2 (5)C4B—C5B—C6B—N1B1.1 (4)
C4A—C5A—C6A—S14A179.6 (2)C4B—C5B—C6B—S14B179.2 (2)
N3A—C4A—S7A—C8A173.4 (2)N3B—C4B—S7B—C8B169.2 (2)
C5A—C4A—S7A—C8A6.4 (3)C5B—C4B—S7B—C8B10.9 (3)
C4A—S7A—C8A—C9A96.5 (3)C4B—S7B—C8B—C9B89.3 (3)
C4A—S7A—C8A—C13A88.8 (3)C4B—S7B—C8B—C13B95.8 (3)
C13A—C8A—C9A—C10A0.4 (5)C13B—C8B—C9B—C10B1.4 (5)
S7A—C8A—C9A—C10A174.3 (3)S7B—C8B—C9B—C10B173.6 (2)
C8A—C9A—C10A—C11A0.2 (5)C8B—C9B—C10B—C11B0.6 (5)
C9A—C10A—C11A—C12A0.3 (5)C9B—C10B—C11B—C12B2.0 (5)
C9A—C10A—C11A—Cl1A178.8 (3)C9B—C10B—C11B—Cl1B176.8 (3)
C10A—C11A—C12A—C13A0.6 (5)C10B—C11B—C12B—C13B1.3 (5)
Cl1A—C11A—C12A—C13A178.4 (3)Cl1B—C11B—C12B—C13B177.5 (3)
C11A—C12A—C13A—C8A0.5 (5)C11B—C12B—C13B—C8B0.8 (5)
C9A—C8A—C13A—C12A0.0 (5)C9B—C8B—C13B—C12B2.1 (5)
S7A—C8A—C13A—C12A174.7 (3)S7B—C8B—C13B—C12B172.8 (2)
N1A—C6A—S14A—C15A171.6 (2)N1B—C6B—S14B—C15B173.1 (2)
C5A—C6A—S14A—C15A7.9 (3)C5B—C6B—S14B—C15B7.1 (3)
C6A—S14A—C15A—C16A87.6 (3)C6B—S14B—C15B—C20B80.6 (3)
C6A—S14A—C15A—C20A96.2 (3)C6B—S14B—C15B—C16B103.1 (3)
C20A—C15A—C16A—C17A0.2 (5)C20B—C15B—C16B—C17B1.7 (5)
S14A—C15A—C16A—C17A176.4 (3)S14B—C15B—C16B—C17B178.0 (3)
C15A—C16A—C17A—C18A0.7 (5)C15B—C16B—C17B—C18B0.9 (5)
C16A—C17A—C18A—C19A1.1 (6)C16B—C17B—C18B—C19B0.6 (6)
C16A—C17A—C18A—Cl2A179.0 (3)C16B—C17B—C18B—Cl2B179.8 (3)
C17A—C18A—C19A—C20A1.0 (6)C17B—C18B—C19B—C20B1.2 (6)
Cl2A—C18A—C19A—C20A179.1 (3)Cl2B—C18B—C19B—C20B179.7 (3)
C18A—C19A—C20A—C15A0.5 (5)C16B—C15B—C20B—C19B2.3 (5)
C16A—C15A—C20A—C19A0.1 (5)S14B—C15B—C20B—C19B178.6 (3)
S14A—C15A—C20A—C19A176.4 (3)C18B—C19B—C20B—C15B2.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21A—H21A···N3Ai0.79 (4)2.38 (4)3.165 (4)175 (3)
N21A—H21A···S7Ai0.79 (4)2.84 (3)3.284 (3)118 (3)
N21B—H21B···N3Bii0.82 (3)2.37 (3)3.187 (4)178 (3)
N21B—H21B···S7Bii0.82 (3)2.86 (3)3.340 (3)120 (2)
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC32H22Cl4N6S4
Mr760.60
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)28.4777 (13), 8.6020 (3), 14.2055 (5)
β (°) 102.5620 (13)
V3)3396.5 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.63
Crystal size (mm)0.15 × 0.15 × 0.10
Data collection
DiffractometerEnraf Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
SORTAV (Blessing, 1995)
Tmin, Tmax0.912, 0.940
No. of measured, independent and
observed [I > 2σ(I)] reflections
20121, 7363, 4286
Rint0.080
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.148, 0.97
No. of reflections7363
No. of parameters432
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.33, 0.39

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21A—H21A···N3Ai0.79 (4)2.38 (4)3.165 (4)175 (3)
N21A—H21A···S7Ai0.79 (4)2.84 (3)3.284 (3)118 (3)
N21B—H21B···N3Bii0.82 (3)2.37 (3)3.187 (4)178 (3)
N21B—H21B···S7Bii0.82 (3)2.86 (3)3.340 (3)120 (2)
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x, y+1/2, z+1/2.
 

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