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The structure of the title compound, C11H8Cl2N2S, comprises two unique mol­ecules with the dihedral angles between the two linked rings for each mol­ecule being 77.1 (1) and 78.4 (1)°. Only one C—H...X short contact exists from an aromatic C—H group to a Cl atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801003154/bt6016sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801003154/bt6016Isup2.hkl
Contains datablock I

CCDC reference: 159866

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.086
  • Data-to-parameter ratio = 17.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 5186 Count of symmetry unique reflns 3046 Completeness (_total/calc) 170.26% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2140 Fraction of Friedel pairs measured 0.703 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.

Comment top

The title compound, (I), is an analogue of 4,6-dichloro-2-methylthiopyrimidine (dcmtp; Lynch & McClenaghan, 2000). In dcmtp, the Cl atoms are displaced by nucleophiles first, before the methylthio group, although the second Cl atom is much less reactive than the first one. In terms of substituent effects, the presence of the phenyl ring in (I) should increase the activity of the Cl atoms, but as found for 4,6-dichloro-2-amino-5-phenylpyrimidine, nucleophilic displacement of the first Cl atom takes reaction times of hours, whereas that of the second takes days. This rate difference may be due to steric effects, thus we have instigated a series of studies to examine the structural changes that the phenyl ring imposes on the nucleophilic substituents of several different analogues of (I), including the 2-amino series. Here we report the single-crystal structure of (I) as our point of reference for further derivatized compounds in the 2-methylthio series.

Experimental top

The title compound, (I), was prepared by Spa Contract Synthesis. Crystals of (I) formed when the reaction solution (POCl3) was poured into excess water.

Refinement top

All H atoms were included in the refinement at calculated positions as riding models with C—H distances set to 0.95 (Ar—H) and 0.98 Å (CH3). The number of Friedel pairs is 2167.

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); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular configuration and atom-numbering scheme for (I), showing 50% probability ellipsoids.
4,6-Dichloro-2-methylthio-5-phenylpyrimidine top
Crystal data top
C11H8Cl2N2SDx = 1.540 Mg m3
Mr = 271.15Melting point: 386-388 K K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 7.467 (2) ÅCell parameters from 9258 reflections
b = 16.217 (3) Åθ = 1.0–27.5°
c = 19.318 (4) ŵ = 0.70 mm1
V = 2339.1 (8) Å3T = 150 K
Z = 8Prism, colourless
F(000) = 11040.28 × 0.24 × 0.20 mm
Data collection top
Enraf Nonius KappaCCD area-detector
diffractometer
5186 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode4655 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 1.6°
ϕ and ω scansh = 99
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 1920
Tmin = 0.827, Tmax = 0.872l = 2424
11464 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)] = 0.034H-atom parameters constrained
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.040P)2 + 0.3307P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.010
5186 reflectionsΔρmax = 0.23 e Å3
291 parametersΔρmin = 0.31 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.04 (5)
Crystal data top
C11H8Cl2N2SV = 2339.1 (8) Å3
Mr = 271.15Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 7.467 (2) ŵ = 0.70 mm1
b = 16.217 (3) ÅT = 150 K
c = 19.318 (4) Å0.28 × 0.24 × 0.20 mm
Data collection top
Enraf Nonius KappaCCD area-detector
diffractometer
5186 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
4655 reflections with I > 2σ(I)
Tmin = 0.827, Tmax = 0.872Rint = 0.045
11464 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.087Δρmax = 0.23 e Å3
S = 1.06Δρmin = 0.31 e Å3
5186 reflectionsAbsolute structure: Flack (1983)
291 parametersAbsolute structure parameter: 0.04 (5)
0 restraints
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)

- 1.3237 (0.0067) x + 15.8160 (0.0044) y + 2.5481 (0.0167) z = 12.3661 (0.0161)

* 0.0121 (0.0015) N1A * -0.0103 (0.0016) C2A * -0.0033 (0.0014) N3A * 0.0138 (0.0015) C4A * -0.0104 (0.0015) C5A * -0.0020 (0.0016) C6A

Rms deviation of fitted atoms = 0.0097

- 6.0999 (0.0043) x + 0.0459 (0.0200) y + 11.1404 (0.0153) z = 1.4378 (0.0202)

Angle to previous plane (with approximate e.s.d.) = 77.08 (0.09)

* 0.0065 (0.0017) C51A * -0.0040 (0.0018) C52A * -0.0013 (0.0019) C53A * 0.0042 (0.0018) C54A * -0.0017 (0.0020) C55A * -0.0036 (0.0019) C56A

Rms deviation of fitted atoms = 0.0040

0.6484 (0.0066) x + 15.9835 (0.0039) y - 2.8021 (0.0162) z = 6.3633 (0.0158)

Angle to previous plane (with approximate e.s.d.) = 81.27 (0.09)

* 0.0015 (0.0015) N3B * 0.0095 (0.0015) C2B * -0.0102 (0.0015) N1B * 0.0013 (0.0015) C6B * 0.0087 (0.0016) C5B * -0.0108 (0.0016) C4B

Rms deviation of fitted atoms = 0.0081

- 6.1618 (0.0045) x + 5.5556 (0.0164) y + 8.6739 (0.0181) z = 6.2361 (0.0144)

Angle to previous plane (with approximate e.s.d.) = 78.41 (0.08)

* -0.0007 (0.0017) C51B * 0.0024 (0.0017) C56B * -0.0036 (0.0018) C55B * 0.0032 (0.0018) C54B * -0.0016 (0.0019) C53B * 0.0004 (0.0018) C52B

Rms deviation of fitted atoms = 0.0023

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A1.0876 (2)0.73835 (12)0.83987 (9)0.0236 (4)
C2A1.2629 (3)0.75264 (14)0.83347 (11)0.0235 (5)
S21A1.40306 (8)0.75031 (4)0.90600 (3)0.03031 (15)
C22A1.2543 (4)0.71986 (18)0.97427 (13)0.0383 (6)
H21A1.14970.75640.97470.048*
H22A1.31670.72371.01880.048*
H23A1.21520.66290.96660.048*
N3A1.3499 (3)0.76982 (12)0.77472 (10)0.0252 (4)
C4A1.2509 (3)0.77174 (13)0.71816 (11)0.0242 (5)
Cl4A1.36552 (8)0.79749 (4)0.64325 (3)0.03203 (14)
C5A1.0677 (3)0.75529 (14)0.71556 (12)0.0232 (5)
C6A0.9970 (3)0.73938 (13)0.78087 (12)0.0224 (5)
Cl6A0.76906 (7)0.72124 (4)0.78894 (3)0.02915 (14)
C51A0.9582 (3)0.75736 (14)0.65118 (12)0.0239 (5)
C52A0.9080 (3)0.83244 (15)0.62246 (13)0.0304 (5)
H52A0.94730.88250.64290.038*
C53A0.8007 (4)0.83422 (16)0.56394 (13)0.0331 (6)
H53A0.76640.88580.54480.041*
C54A0.7431 (3)0.76239 (16)0.53317 (12)0.0330 (6)
H54A0.66890.76420.49320.041*
C55A0.7945 (4)0.68764 (16)0.56108 (13)0.0372 (6)
H55A0.75600.63780.54000.047*
C56A0.9018 (4)0.68470 (15)0.61967 (12)0.0316 (6)
H56A0.93680.63300.63830.040*
N3B0.8384 (2)0.51428 (12)0.85606 (10)0.0249 (4)
C2B0.7390 (3)0.52873 (13)0.91267 (11)0.0245 (5)
S21B0.86920 (9)0.53870 (4)0.98740 (3)0.03428 (16)
C22B0.7031 (4)0.55036 (18)1.05312 (12)0.0389 (6)
H21B0.63380.60061.04440.049*
H22B0.76150.55441.09840.049*
H23B0.62290.50251.05260.049*
N1B0.5613 (3)0.53514 (12)0.91511 (10)0.0242 (4)
C6B0.4796 (3)0.52853 (13)0.85443 (12)0.0224 (5)
CL6B0.24915 (7)0.53895 (4)0.85646 (3)0.02876 (14)
C5B0.5636 (3)0.51451 (14)0.79125 (12)0.0217 (5)
C4B0.7487 (3)0.50696 (14)0.79796 (11)0.0238 (5)
CL4B0.87945 (8)0.48429 (4)0.72652 (3)0.03379 (15)
C51B0.4662 (3)0.50886 (14)0.72414 (12)0.0227 (5)
C56B0.3751 (3)0.43736 (14)0.70554 (12)0.0278 (5)
H56B0.37500.39120.73580.035*
C55B0.2847 (3)0.43327 (15)0.64327 (13)0.0316 (5)
H55B0.22420.38390.63090.039*
C54B0.2810 (3)0.49964 (16)0.59888 (12)0.0297 (5)
H54B0.21710.49650.55640.037*
C53B0.3720 (4)0.57154 (16)0.61696 (12)0.0337 (6)
H53B0.37120.61750.58640.042*
C52B0.4632 (3)0.57640 (15)0.67886 (13)0.0303 (5)
H52B0.52430.62570.69090.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0200 (9)0.0285 (9)0.0223 (10)0.0008 (8)0.0012 (7)0.0004 (8)
C2A0.0203 (11)0.0272 (10)0.0229 (11)0.0011 (10)0.0009 (9)0.0019 (9)
S21A0.0221 (3)0.0475 (3)0.0213 (3)0.0024 (3)0.0017 (2)0.0012 (3)
C22A0.0343 (14)0.0569 (16)0.0238 (13)0.0036 (14)0.0010 (12)0.0062 (11)
N3A0.0205 (9)0.0336 (10)0.0215 (9)0.0016 (8)0.0022 (8)0.0017 (8)
C4A0.0244 (11)0.0280 (11)0.0203 (11)0.0020 (10)0.0040 (10)0.0013 (9)
Cl4A0.0300 (3)0.0433 (3)0.0227 (3)0.0063 (3)0.0059 (3)0.0012 (2)
C5A0.0224 (11)0.0205 (10)0.0265 (12)0.0000 (9)0.0010 (9)0.0010 (9)
C6A0.0180 (10)0.0220 (10)0.0273 (12)0.0004 (9)0.0014 (9)0.0010 (9)
Cl6A0.0177 (3)0.0376 (3)0.0322 (3)0.0022 (2)0.0016 (2)0.0007 (2)
C51A0.0221 (11)0.0278 (11)0.0218 (11)0.0026 (10)0.0001 (9)0.0003 (9)
C52A0.0323 (13)0.0273 (12)0.0317 (13)0.0010 (11)0.0039 (11)0.0010 (10)
C53A0.0353 (13)0.0370 (13)0.0270 (13)0.0035 (11)0.0034 (11)0.0044 (11)
C54A0.0279 (12)0.0517 (15)0.0194 (12)0.0021 (13)0.0008 (10)0.0014 (10)
C55A0.0453 (15)0.0364 (13)0.0301 (14)0.0124 (12)0.0074 (12)0.0036 (11)
C56A0.0387 (15)0.0269 (11)0.0294 (13)0.0036 (12)0.0045 (12)0.0010 (10)
N3B0.0203 (9)0.0343 (10)0.0202 (10)0.0012 (8)0.0007 (8)0.0020 (8)
C2B0.0236 (11)0.0274 (11)0.0224 (11)0.0009 (10)0.0022 (10)0.0033 (9)
S21B0.0269 (3)0.0566 (4)0.0194 (3)0.0038 (3)0.0041 (3)0.0020 (3)
C22B0.0422 (15)0.0526 (16)0.0219 (12)0.0062 (14)0.0026 (11)0.0006 (12)
N1B0.0229 (10)0.0273 (9)0.0223 (10)0.0003 (8)0.0006 (8)0.0020 (8)
C6B0.0186 (10)0.0229 (10)0.0258 (12)0.0013 (9)0.0002 (10)0.0008 (9)
CL6B0.0183 (3)0.0369 (3)0.0311 (3)0.0013 (3)0.0007 (2)0.0022 (2)
C5B0.0217 (11)0.0227 (10)0.0207 (11)0.0005 (9)0.0038 (9)0.0023 (9)
C4B0.0214 (11)0.0264 (10)0.0235 (11)0.0007 (10)0.0015 (10)0.0017 (9)
CL4B0.0267 (3)0.0529 (4)0.0217 (3)0.0057 (3)0.0019 (3)0.0001 (3)
C51B0.0192 (10)0.0273 (11)0.0215 (12)0.0022 (9)0.0009 (9)0.0002 (9)
C56B0.0298 (12)0.0275 (11)0.0260 (11)0.0009 (11)0.0033 (11)0.0004 (9)
C55B0.0286 (13)0.0341 (12)0.0320 (13)0.0030 (11)0.0023 (11)0.0065 (11)
C54B0.0262 (12)0.0444 (14)0.0186 (11)0.0030 (12)0.0036 (10)0.0013 (10)
C53B0.0363 (14)0.0377 (13)0.0270 (12)0.0013 (13)0.0047 (12)0.0072 (10)
C52B0.0342 (14)0.0302 (12)0.0266 (12)0.0018 (11)0.0049 (11)0.0027 (10)
Geometric parameters (Å, º) top
N1A—C6A1.326 (3)N3B—C4B1.312 (3)
N1A—C2A1.335 (3)N3B—C2B1.342 (3)
C2A—N3A1.337 (3)C2B—N1B1.332 (3)
C2A—S21A1.749 (2)C2B—S21B1.748 (2)
S21A—C22A1.794 (3)S21B—C22B1.785 (3)
C22A—H21A0.98C22B—H21B0.98
C22A—H22A0.98C22B—H22B0.98
C22A—H23A0.98C22B—H23B0.98
N3A—C4A1.319 (3)N1B—C6B1.326 (3)
C4A—C5A1.395 (3)C6B—C5B1.391 (3)
C4A—Cl4A1.732 (2)C6B—CL6B1.729 (2)
C5A—C6A1.392 (3)C5B—C4B1.394 (3)
C5A—C51A1.489 (3)C5B—C51B1.489 (3)
C6A—Cl6A1.734 (2)C4B—CL4B1.730 (2)
C51A—C52A1.389 (3)C51B—C56B1.392 (3)
C51A—C56A1.392 (3)C51B—C52B1.402 (3)
C52A—C53A1.386 (3)C56B—C55B1.381 (3)
C52A—H52A0.95C56B—H56B0.95
C53A—C54A1.377 (4)C55B—C54B1.377 (3)
C53A—H53A0.95C55B—H55B0.95
C54A—C55A1.381 (4)C54B—C53B1.394 (4)
C54A—H54A0.95C54B—H54B0.95
C55A—C56A1.388 (4)C53B—C52B1.378 (3)
C55A—H55A0.95C53B—H53B0.95
C56A—H56A0.95C52B—H52B0.95
C6A—N1A—C2A114.76 (18)C4B—N3B—C2B115.51 (19)
N3A—C2A—N1A126.2 (2)N1B—C2B—N3B126.4 (2)
N3A—C2A—S21A113.19 (17)N1B—C2B—S21B121.18 (18)
N1A—C2A—S21A120.57 (17)N3B—C2B—S21B112.43 (17)
C2A—S21A—C22A102.96 (12)C2B—S21B—C22B102.18 (12)
S21A—C22A—H21A109.5S21B—C22B—H21B109.5
S21A—C22A—H22A109.5S21B—C22B—H22B109.5
H21A—C22A—H22A109.5H21B—C22B—H22B109.5
S21A—C22A—H23A109.5S21B—C22B—H23B109.5
H21A—C22A—H23A109.5H21B—C22B—H23B109.5
H22A—C22A—H23A109.5H22B—C22B—H23B109.5
C4A—N3A—C2A115.84 (19)C6B—N1B—C2B114.89 (19)
N3A—C4A—C5A125.1 (2)N1B—C6B—C5B125.6 (2)
N3A—C4A—Cl4A114.88 (17)N1B—C6B—CL6B115.45 (17)
C5A—C4A—Cl4A120.04 (18)C5B—C6B—CL6B118.98 (17)
C6A—C5A—C4A112.0 (2)C6B—C5B—C4B112.3 (2)
C6A—C5A—C51A123.6 (2)C6B—C5B—C51B123.6 (2)
C4A—C5A—C51A124.4 (2)C4B—C5B—C51B124.0 (2)
N1A—C6A—C5A126.0 (2)N3B—C4B—C5B125.3 (2)
N1A—C6A—Cl6A114.94 (16)N3B—C4B—CL4B114.44 (18)
C5A—C6A—Cl6A119.03 (17)C5B—C4B—CL4B120.28 (18)
C52A—C51A—C56A119.1 (2)C56B—C51B—C52B118.8 (2)
C52A—C51A—C5A120.1 (2)C56B—C51B—C5B121.0 (2)
C56A—C51A—C5A120.8 (2)C52B—C51B—C5B120.2 (2)
C53A—C52A—C51A120.0 (2)C55B—C56B—C51B120.3 (2)
C53A—C52A—H52A120.0C55B—C56B—H56B119.9
C51A—C52A—H52A120.0C51B—C56B—H56B119.9
C54A—C53A—C52A121.0 (2)C54B—C55B—C56B121.0 (2)
C54A—C53A—H53A119.5C54B—C55B—H55B119.5
C52A—C53A—H53A119.5C56B—C55B—H55B119.5
C53A—C54A—C55A119.2 (2)C55B—C54B—C53B119.2 (2)
C53A—C54A—H54A120.4C55B—C54B—H54B120.4
C55A—C54A—H54A120.4C53B—C54B—H54B120.4
C54A—C55A—C56A120.6 (2)C52B—C53B—C54B120.4 (2)
C54A—C55A—H55A119.7C52B—C53B—H53B119.8
C56A—C55A—H55A119.7C54B—C53B—H53B119.8
C55A—C56A—C51A120.2 (2)C53B—C52B—C51B120.3 (2)
C55A—C56A—H56A119.9C53B—C52B—H52B119.8
C51A—C56A—H56A119.9C51B—C52B—H52B119.8
C6A—N1A—C2A—N3A2.2 (3)C4B—N3B—C2B—N1B0.9 (4)
C6A—N1A—C2A—S21A178.03 (16)C4B—N3B—C2B—S21B179.36 (17)
N3A—C2A—S21A—C22A176.45 (18)N1B—C2B—S21B—C22B3.4 (2)
N1A—C2A—S21A—C22A3.7 (2)N3B—C2B—S21B—C22B176.39 (18)
N1A—C2A—N3A—C4A0.7 (3)N3B—C2B—N1B—C6B2.0 (3)
S21A—C2A—N3A—C4A179.47 (16)S21B—C2B—N1B—C6B178.26 (16)
C2A—N3A—C4A—C5A1.8 (3)C2B—N1B—C6B—C5B1.1 (3)
C2A—N3A—C4A—Cl4A177.96 (17)C2B—N1B—C6B—CL6B178.65 (17)
N3A—C4A—C5A—C6A2.4 (3)N1B—C6B—C5B—C4B0.6 (3)
Cl4A—C4A—C5A—C6A177.33 (16)CL6B—C6B—C5B—C4B179.61 (16)
N3A—C4A—C5A—C51A179.7 (2)N1B—C6B—C5B—C51B179.0 (2)
Cl4A—C4A—C5A—C51A0.6 (3)CL6B—C6B—C5B—C51B0.8 (3)
C2A—N1A—C6A—C5A1.4 (3)C2B—N3B—C4B—C5B1.2 (4)
C2A—N1A—C6A—Cl6A179.77 (17)C2B—N3B—C4B—CL4B177.55 (16)
C4A—C5A—C6A—N1A0.7 (3)C6B—C5B—C4B—N3B1.9 (4)
C51A—C5A—C6A—N1A178.6 (2)C51B—C5B—C4B—N3B177.7 (2)
C4A—C5A—C6A—Cl6A177.64 (16)C6B—C5B—C4B—CL4B176.84 (16)
C51A—C5A—C6A—Cl6A0.3 (3)C51B—C5B—C4B—CL4B3.6 (3)
C6A—C5A—C51A—C52A101.6 (3)C6B—C5B—C51B—C56B78.5 (3)
C4A—C5A—C51A—C52A76.1 (3)C4B—C5B—C51B—C56B102.0 (3)
C6A—C5A—C51A—C56A77.2 (3)C6B—C5B—C51B—C52B100.7 (3)
C4A—C5A—C51A—C56A105.2 (3)C4B—C5B—C51B—C52B78.8 (3)
C56A—C51A—C52A—C53A1.1 (4)C52B—C51B—C56B—C55B0.5 (4)
C5A—C51A—C52A—C53A177.7 (2)C5B—C51B—C56B—C55B179.7 (2)
C51A—C52A—C53A—C54A0.4 (4)C51B—C56B—C55B—C54B0.8 (4)
C52A—C53A—C54A—C55A0.4 (4)C56B—C55B—C54B—C53B0.8 (4)
C53A—C54A—C55A—C56A0.5 (4)C55B—C54B—C53B—C52B0.6 (4)
C54A—C55A—C56A—C51A0.3 (4)C54B—C53B—C52B—C51B0.4 (4)
C52A—C51A—C56A—C55A1.1 (4)C56B—C51B—C52B—C53B0.3 (4)
C5A—C51A—C56A—C55A177.7 (2)C5B—C51B—C52B—C53B179.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22B—H22B···CL4Bi0.982.763.452 (3)128
Symmetry code: (i) x+3/2, y+1, z+1/2.

Experimental details

Crystal data
Chemical formulaC11H8Cl2N2S
Mr271.15
Crystal system, space groupOrthorhombic, P212121
Temperature (K)150
a, b, c (Å)7.467 (2), 16.217 (3), 19.318 (4)
V3)2339.1 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.70
Crystal size (mm)0.28 × 0.24 × 0.20
Data collection
DiffractometerEnraf Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.827, 0.872
No. of measured, independent and
observed [I > 2σ(I)] reflections
11464, 5186, 4655
Rint0.045
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.087, 1.06
No. of reflections5186
No. of parameters291
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.31
Absolute structureFlack (1983)
Absolute structure parameter0.04 (5)

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON97 (Spek, 1997), SHELXL97.

Selected torsion angles (º) top
N1A—C2A—S21A—C22A3.7 (2)N1B—C2B—S21B—C22B3.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22B—H22B···CL4Bi0.982.763.452 (3)128.0
Symmetry code: (i) x+3/2, y+1, z+1/2.
 

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