Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801003154/bt6016sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801003154/bt6016Isup2.hkl |
CCDC reference: 159866
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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.
The title compound, (I), was prepared by Spa Contract Synthesis. Crystals of (I) formed when the reaction solution (POCl3) was poured into excess water.
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.
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.
Fig. 1. The molecular configuration and atom-numbering scheme for (I), showing 50% probability ellipsoids. |
C11H8Cl2N2S | Dx = 1.540 Mg m−3 |
Mr = 271.15 | Melting point: 386-388 K K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.467 (2) Å | Cell parameters from 9258 reflections |
b = 16.217 (3) Å | θ = 1.0–27.5° |
c = 19.318 (4) Å | µ = 0.70 mm−1 |
V = 2339.1 (8) Å3 | T = 150 K |
Z = 8 | Prism, colourless |
F(000) = 1104 | 0.28 × 0.24 × 0.20 mm |
Enraf Nonius KappaCCD area-detector diffractometer | 5186 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 4655 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 1.6° |
ϕ and ω scans | h = −9→9 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −19→20 |
Tmin = 0.827, Tmax = 0.872 | l = −24→24 |
11464 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-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 reflections | Δρmax = 0.23 e Å−3 |
291 parameters | Δρmin = −0.31 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.04 (5) |
C11H8Cl2N2S | V = 2339.1 (8) Å3 |
Mr = 271.15 | Z = 8 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.467 (2) Å | µ = 0.70 mm−1 |
b = 16.217 (3) Å | T = 150 K |
c = 19.318 (4) Å | 0.28 × 0.24 × 0.20 mm |
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 = 0.872 | Rint = 0.045 |
11464 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.087 | Δρmax = 0.23 e Å−3 |
S = 1.06 | Δρmin = −0.31 e Å−3 |
5186 reflections | Absolute structure: Flack (1983) |
291 parameters | Absolute structure parameter: −0.04 (5) |
0 restraints |
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 |
x | y | z | Uiso*/Ueq | ||
N1A | 1.0876 (2) | 0.73835 (12) | 0.83987 (9) | 0.0236 (4) | |
C2A | 1.2629 (3) | 0.75264 (14) | 0.83347 (11) | 0.0235 (5) | |
S21A | 1.40306 (8) | 0.75031 (4) | 0.90600 (3) | 0.03031 (15) | |
C22A | 1.2543 (4) | 0.71986 (18) | 0.97427 (13) | 0.0383 (6) | |
H21A | 1.1497 | 0.7564 | 0.9747 | 0.048* | |
H22A | 1.3167 | 0.7237 | 1.0188 | 0.048* | |
H23A | 1.2152 | 0.6629 | 0.9666 | 0.048* | |
N3A | 1.3499 (3) | 0.76982 (12) | 0.77472 (10) | 0.0252 (4) | |
C4A | 1.2509 (3) | 0.77174 (13) | 0.71816 (11) | 0.0242 (5) | |
Cl4A | 1.36552 (8) | 0.79749 (4) | 0.64325 (3) | 0.03203 (14) | |
C5A | 1.0677 (3) | 0.75529 (14) | 0.71556 (12) | 0.0232 (5) | |
C6A | 0.9970 (3) | 0.73938 (13) | 0.78087 (12) | 0.0224 (5) | |
Cl6A | 0.76906 (7) | 0.72124 (4) | 0.78894 (3) | 0.02915 (14) | |
C51A | 0.9582 (3) | 0.75736 (14) | 0.65118 (12) | 0.0239 (5) | |
C52A | 0.9080 (3) | 0.83244 (15) | 0.62246 (13) | 0.0304 (5) | |
H52A | 0.9473 | 0.8825 | 0.6429 | 0.038* | |
C53A | 0.8007 (4) | 0.83422 (16) | 0.56394 (13) | 0.0331 (6) | |
H53A | 0.7664 | 0.8858 | 0.5448 | 0.041* | |
C54A | 0.7431 (3) | 0.76239 (16) | 0.53317 (12) | 0.0330 (6) | |
H54A | 0.6689 | 0.7642 | 0.4932 | 0.041* | |
C55A | 0.7945 (4) | 0.68764 (16) | 0.56108 (13) | 0.0372 (6) | |
H55A | 0.7560 | 0.6378 | 0.5400 | 0.047* | |
C56A | 0.9018 (4) | 0.68470 (15) | 0.61967 (12) | 0.0316 (6) | |
H56A | 0.9368 | 0.6330 | 0.6383 | 0.040* | |
N3B | 0.8384 (2) | 0.51428 (12) | 0.85606 (10) | 0.0249 (4) | |
C2B | 0.7390 (3) | 0.52873 (13) | 0.91267 (11) | 0.0245 (5) | |
S21B | 0.86920 (9) | 0.53870 (4) | 0.98740 (3) | 0.03428 (16) | |
C22B | 0.7031 (4) | 0.55036 (18) | 1.05312 (12) | 0.0389 (6) | |
H21B | 0.6338 | 0.6006 | 1.0444 | 0.049* | |
H22B | 0.7615 | 0.5544 | 1.0984 | 0.049* | |
H23B | 0.6229 | 0.5025 | 1.0526 | 0.049* | |
N1B | 0.5613 (3) | 0.53514 (12) | 0.91511 (10) | 0.0242 (4) | |
C6B | 0.4796 (3) | 0.52853 (13) | 0.85443 (12) | 0.0224 (5) | |
CL6B | 0.24915 (7) | 0.53895 (4) | 0.85646 (3) | 0.02876 (14) | |
C5B | 0.5636 (3) | 0.51451 (14) | 0.79125 (12) | 0.0217 (5) | |
C4B | 0.7487 (3) | 0.50696 (14) | 0.79796 (11) | 0.0238 (5) | |
CL4B | 0.87945 (8) | 0.48429 (4) | 0.72652 (3) | 0.03379 (15) | |
C51B | 0.4662 (3) | 0.50886 (14) | 0.72414 (12) | 0.0227 (5) | |
C56B | 0.3751 (3) | 0.43736 (14) | 0.70554 (12) | 0.0278 (5) | |
H56B | 0.3750 | 0.3912 | 0.7358 | 0.035* | |
C55B | 0.2847 (3) | 0.43327 (15) | 0.64327 (13) | 0.0316 (5) | |
H55B | 0.2242 | 0.3839 | 0.6309 | 0.039* | |
C54B | 0.2810 (3) | 0.49964 (16) | 0.59888 (12) | 0.0297 (5) | |
H54B | 0.2171 | 0.4965 | 0.5564 | 0.037* | |
C53B | 0.3720 (4) | 0.57154 (16) | 0.61696 (12) | 0.0337 (6) | |
H53B | 0.3712 | 0.6175 | 0.5864 | 0.042* | |
C52B | 0.4632 (3) | 0.57640 (15) | 0.67886 (13) | 0.0303 (5) | |
H52B | 0.5243 | 0.6257 | 0.6909 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0200 (9) | 0.0285 (9) | 0.0223 (10) | 0.0008 (8) | 0.0012 (7) | −0.0004 (8) |
C2A | 0.0203 (11) | 0.0272 (10) | 0.0229 (11) | 0.0011 (10) | 0.0009 (9) | −0.0019 (9) |
S21A | 0.0221 (3) | 0.0475 (3) | 0.0213 (3) | −0.0024 (3) | −0.0017 (2) | 0.0012 (3) |
C22A | 0.0343 (14) | 0.0569 (16) | 0.0238 (13) | −0.0036 (14) | 0.0010 (12) | 0.0062 (11) |
N3A | 0.0205 (9) | 0.0336 (10) | 0.0215 (9) | −0.0016 (8) | 0.0022 (8) | −0.0017 (8) |
C4A | 0.0244 (11) | 0.0280 (11) | 0.0203 (11) | −0.0020 (10) | 0.0040 (10) | −0.0013 (9) |
Cl4A | 0.0300 (3) | 0.0433 (3) | 0.0227 (3) | −0.0063 (3) | 0.0059 (3) | 0.0012 (2) |
C5A | 0.0224 (11) | 0.0205 (10) | 0.0265 (12) | 0.0000 (9) | 0.0010 (9) | −0.0010 (9) |
C6A | 0.0180 (10) | 0.0220 (10) | 0.0273 (12) | 0.0004 (9) | 0.0014 (9) | −0.0010 (9) |
Cl6A | 0.0177 (3) | 0.0376 (3) | 0.0322 (3) | −0.0022 (2) | 0.0016 (2) | −0.0007 (2) |
C51A | 0.0221 (11) | 0.0278 (11) | 0.0218 (11) | −0.0026 (10) | 0.0001 (9) | 0.0003 (9) |
C52A | 0.0323 (13) | 0.0273 (12) | 0.0317 (13) | 0.0010 (11) | −0.0039 (11) | 0.0010 (10) |
C53A | 0.0353 (13) | 0.0370 (13) | 0.0270 (13) | 0.0035 (11) | −0.0034 (11) | 0.0044 (11) |
C54A | 0.0279 (12) | 0.0517 (15) | 0.0194 (12) | −0.0021 (13) | −0.0008 (10) | 0.0014 (10) |
C55A | 0.0453 (15) | 0.0364 (13) | 0.0301 (14) | −0.0124 (12) | −0.0074 (12) | −0.0036 (11) |
C56A | 0.0387 (15) | 0.0269 (11) | 0.0294 (13) | −0.0036 (12) | −0.0045 (12) | 0.0010 (10) |
N3B | 0.0203 (9) | 0.0343 (10) | 0.0202 (10) | 0.0012 (8) | −0.0007 (8) | 0.0020 (8) |
C2B | 0.0236 (11) | 0.0274 (11) | 0.0224 (11) | −0.0009 (10) | −0.0022 (10) | 0.0033 (9) |
S21B | 0.0269 (3) | 0.0566 (4) | 0.0194 (3) | −0.0038 (3) | −0.0041 (3) | 0.0020 (3) |
C22B | 0.0422 (15) | 0.0526 (16) | 0.0219 (12) | −0.0062 (14) | 0.0026 (11) | 0.0006 (12) |
N1B | 0.0229 (10) | 0.0273 (9) | 0.0223 (10) | −0.0003 (8) | −0.0006 (8) | 0.0020 (8) |
C6B | 0.0186 (10) | 0.0229 (10) | 0.0258 (12) | 0.0013 (9) | 0.0002 (10) | 0.0008 (9) |
CL6B | 0.0183 (3) | 0.0369 (3) | 0.0311 (3) | 0.0013 (3) | 0.0007 (2) | −0.0022 (2) |
C5B | 0.0217 (11) | 0.0227 (10) | 0.0207 (11) | 0.0005 (9) | −0.0038 (9) | 0.0023 (9) |
C4B | 0.0214 (11) | 0.0264 (10) | 0.0235 (11) | 0.0007 (10) | 0.0015 (10) | 0.0017 (9) |
CL4B | 0.0267 (3) | 0.0529 (4) | 0.0217 (3) | 0.0057 (3) | 0.0019 (3) | −0.0001 (3) |
C51B | 0.0192 (10) | 0.0273 (11) | 0.0215 (12) | 0.0022 (9) | −0.0009 (9) | 0.0002 (9) |
C56B | 0.0298 (12) | 0.0275 (11) | 0.0260 (11) | −0.0009 (11) | −0.0033 (11) | 0.0004 (9) |
C55B | 0.0286 (13) | 0.0341 (12) | 0.0320 (13) | −0.0030 (11) | −0.0023 (11) | −0.0065 (11) |
C54B | 0.0262 (12) | 0.0444 (14) | 0.0186 (11) | 0.0030 (12) | −0.0036 (10) | −0.0013 (10) |
C53B | 0.0363 (14) | 0.0377 (13) | 0.0270 (12) | −0.0013 (13) | −0.0047 (12) | 0.0072 (10) |
C52B | 0.0342 (14) | 0.0302 (12) | 0.0266 (12) | −0.0018 (11) | −0.0049 (11) | 0.0027 (10) |
N1A—C6A | 1.326 (3) | N3B—C4B | 1.312 (3) |
N1A—C2A | 1.335 (3) | N3B—C2B | 1.342 (3) |
C2A—N3A | 1.337 (3) | C2B—N1B | 1.332 (3) |
C2A—S21A | 1.749 (2) | C2B—S21B | 1.748 (2) |
S21A—C22A | 1.794 (3) | S21B—C22B | 1.785 (3) |
C22A—H21A | 0.98 | C22B—H21B | 0.98 |
C22A—H22A | 0.98 | C22B—H22B | 0.98 |
C22A—H23A | 0.98 | C22B—H23B | 0.98 |
N3A—C4A | 1.319 (3) | N1B—C6B | 1.326 (3) |
C4A—C5A | 1.395 (3) | C6B—C5B | 1.391 (3) |
C4A—Cl4A | 1.732 (2) | C6B—CL6B | 1.729 (2) |
C5A—C6A | 1.392 (3) | C5B—C4B | 1.394 (3) |
C5A—C51A | 1.489 (3) | C5B—C51B | 1.489 (3) |
C6A—Cl6A | 1.734 (2) | C4B—CL4B | 1.730 (2) |
C51A—C52A | 1.389 (3) | C51B—C56B | 1.392 (3) |
C51A—C56A | 1.392 (3) | C51B—C52B | 1.402 (3) |
C52A—C53A | 1.386 (3) | C56B—C55B | 1.381 (3) |
C52A—H52A | 0.95 | C56B—H56B | 0.95 |
C53A—C54A | 1.377 (4) | C55B—C54B | 1.377 (3) |
C53A—H53A | 0.95 | C55B—H55B | 0.95 |
C54A—C55A | 1.381 (4) | C54B—C53B | 1.394 (4) |
C54A—H54A | 0.95 | C54B—H54B | 0.95 |
C55A—C56A | 1.388 (4) | C53B—C52B | 1.378 (3) |
C55A—H55A | 0.95 | C53B—H53B | 0.95 |
C56A—H56A | 0.95 | C52B—H52B | 0.95 |
C6A—N1A—C2A | 114.76 (18) | C4B—N3B—C2B | 115.51 (19) |
N3A—C2A—N1A | 126.2 (2) | N1B—C2B—N3B | 126.4 (2) |
N3A—C2A—S21A | 113.19 (17) | N1B—C2B—S21B | 121.18 (18) |
N1A—C2A—S21A | 120.57 (17) | N3B—C2B—S21B | 112.43 (17) |
C2A—S21A—C22A | 102.96 (12) | C2B—S21B—C22B | 102.18 (12) |
S21A—C22A—H21A | 109.5 | S21B—C22B—H21B | 109.5 |
S21A—C22A—H22A | 109.5 | S21B—C22B—H22B | 109.5 |
H21A—C22A—H22A | 109.5 | H21B—C22B—H22B | 109.5 |
S21A—C22A—H23A | 109.5 | S21B—C22B—H23B | 109.5 |
H21A—C22A—H23A | 109.5 | H21B—C22B—H23B | 109.5 |
H22A—C22A—H23A | 109.5 | H22B—C22B—H23B | 109.5 |
C4A—N3A—C2A | 115.84 (19) | C6B—N1B—C2B | 114.89 (19) |
N3A—C4A—C5A | 125.1 (2) | N1B—C6B—C5B | 125.6 (2) |
N3A—C4A—Cl4A | 114.88 (17) | N1B—C6B—CL6B | 115.45 (17) |
C5A—C4A—Cl4A | 120.04 (18) | C5B—C6B—CL6B | 118.98 (17) |
C6A—C5A—C4A | 112.0 (2) | C6B—C5B—C4B | 112.3 (2) |
C6A—C5A—C51A | 123.6 (2) | C6B—C5B—C51B | 123.6 (2) |
C4A—C5A—C51A | 124.4 (2) | C4B—C5B—C51B | 124.0 (2) |
N1A—C6A—C5A | 126.0 (2) | N3B—C4B—C5B | 125.3 (2) |
N1A—C6A—Cl6A | 114.94 (16) | N3B—C4B—CL4B | 114.44 (18) |
C5A—C6A—Cl6A | 119.03 (17) | C5B—C4B—CL4B | 120.28 (18) |
C52A—C51A—C56A | 119.1 (2) | C56B—C51B—C52B | 118.8 (2) |
C52A—C51A—C5A | 120.1 (2) | C56B—C51B—C5B | 121.0 (2) |
C56A—C51A—C5A | 120.8 (2) | C52B—C51B—C5B | 120.2 (2) |
C53A—C52A—C51A | 120.0 (2) | C55B—C56B—C51B | 120.3 (2) |
C53A—C52A—H52A | 120.0 | C55B—C56B—H56B | 119.9 |
C51A—C52A—H52A | 120.0 | C51B—C56B—H56B | 119.9 |
C54A—C53A—C52A | 121.0 (2) | C54B—C55B—C56B | 121.0 (2) |
C54A—C53A—H53A | 119.5 | C54B—C55B—H55B | 119.5 |
C52A—C53A—H53A | 119.5 | C56B—C55B—H55B | 119.5 |
C53A—C54A—C55A | 119.2 (2) | C55B—C54B—C53B | 119.2 (2) |
C53A—C54A—H54A | 120.4 | C55B—C54B—H54B | 120.4 |
C55A—C54A—H54A | 120.4 | C53B—C54B—H54B | 120.4 |
C54A—C55A—C56A | 120.6 (2) | C52B—C53B—C54B | 120.4 (2) |
C54A—C55A—H55A | 119.7 | C52B—C53B—H53B | 119.8 |
C56A—C55A—H55A | 119.7 | C54B—C53B—H53B | 119.8 |
C55A—C56A—C51A | 120.2 (2) | C53B—C52B—C51B | 120.3 (2) |
C55A—C56A—H56A | 119.9 | C53B—C52B—H52B | 119.8 |
C51A—C56A—H56A | 119.9 | C51B—C52B—H52B | 119.8 |
C6A—N1A—C2A—N3A | 2.2 (3) | C4B—N3B—C2B—N1B | 0.9 (4) |
C6A—N1A—C2A—S21A | −178.03 (16) | C4B—N3B—C2B—S21B | −179.36 (17) |
N3A—C2A—S21A—C22A | −176.45 (18) | N1B—C2B—S21B—C22B | 3.4 (2) |
N1A—C2A—S21A—C22A | 3.7 (2) | N3B—C2B—S21B—C22B | −176.39 (18) |
N1A—C2A—N3A—C4A | −0.7 (3) | N3B—C2B—N1B—C6B | −2.0 (3) |
S21A—C2A—N3A—C4A | 179.47 (16) | S21B—C2B—N1B—C6B | 178.26 (16) |
C2A—N3A—C4A—C5A | −1.8 (3) | C2B—N1B—C6B—C5B | 1.1 (3) |
C2A—N3A—C4A—Cl4A | 177.96 (17) | C2B—N1B—C6B—CL6B | −178.65 (17) |
N3A—C4A—C5A—C6A | 2.4 (3) | N1B—C6B—C5B—C4B | 0.6 (3) |
Cl4A—C4A—C5A—C6A | −177.33 (16) | CL6B—C6B—C5B—C4B | −179.61 (16) |
N3A—C4A—C5A—C51A | −179.7 (2) | N1B—C6B—C5B—C51B | −179.0 (2) |
Cl4A—C4A—C5A—C51A | 0.6 (3) | CL6B—C6B—C5B—C51B | 0.8 (3) |
C2A—N1A—C6A—C5A | −1.4 (3) | C2B—N3B—C4B—C5B | 1.2 (4) |
C2A—N1A—C6A—Cl6A | −179.77 (17) | C2B—N3B—C4B—CL4B | −177.55 (16) |
C4A—C5A—C6A—N1A | −0.7 (3) | C6B—C5B—C4B—N3B | −1.9 (4) |
C51A—C5A—C6A—N1A | −178.6 (2) | C51B—C5B—C4B—N3B | 177.7 (2) |
C4A—C5A—C6A—Cl6A | 177.64 (16) | C6B—C5B—C4B—CL4B | 176.84 (16) |
C51A—C5A—C6A—Cl6A | −0.3 (3) | C51B—C5B—C4B—CL4B | −3.6 (3) |
C6A—C5A—C51A—C52A | 101.6 (3) | C6B—C5B—C51B—C56B | −78.5 (3) |
C4A—C5A—C51A—C52A | −76.1 (3) | C4B—C5B—C51B—C56B | 102.0 (3) |
C6A—C5A—C51A—C56A | −77.2 (3) | C6B—C5B—C51B—C52B | 100.7 (3) |
C4A—C5A—C51A—C56A | 105.2 (3) | C4B—C5B—C51B—C52B | −78.8 (3) |
C56A—C51A—C52A—C53A | 1.1 (4) | C52B—C51B—C56B—C55B | 0.5 (4) |
C5A—C51A—C52A—C53A | −177.7 (2) | C5B—C51B—C56B—C55B | 179.7 (2) |
C51A—C52A—C53A—C54A | −0.4 (4) | C51B—C56B—C55B—C54B | −0.8 (4) |
C52A—C53A—C54A—C55A | −0.4 (4) | C56B—C55B—C54B—C53B | 0.8 (4) |
C53A—C54A—C55A—C56A | 0.5 (4) | C55B—C54B—C53B—C52B | −0.6 (4) |
C54A—C55A—C56A—C51A | 0.3 (4) | C54B—C53B—C52B—C51B | 0.4 (4) |
C52A—C51A—C56A—C55A | −1.1 (4) | C56B—C51B—C52B—C53B | −0.3 (4) |
C5A—C51A—C56A—C55A | 177.7 (2) | C5B—C51B—C52B—C53B | −179.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C22B—H22B···CL4Bi | 0.98 | 2.76 | 3.452 (3) | 128 |
Symmetry code: (i) −x+3/2, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C11H8Cl2N2S |
Mr | 271.15 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 150 |
a, b, c (Å) | 7.467 (2), 16.217 (3), 19.318 (4) |
V (Å3) | 2339.1 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.70 |
Crystal size (mm) | 0.28 × 0.24 × 0.20 |
Data collection | |
Diffractometer | Enraf Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.827, 0.872 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11464, 5186, 4655 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.087, 1.06 |
No. of reflections | 5186 |
No. of parameters | 291 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.31 |
Absolute structure | Flack (1983) |
Absolute structure parameter | −0.04 (5) |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON97 (Spek, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
C22B—H22B···CL4Bi | 0.98 | 2.76 | 3.452 (3) | 128.0 |
Symmetry code: (i) −x+3/2, −y+1, z+1/2. |
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.