Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800017876/ob6000sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536800017876/ob6000Isup2.hkl |
CCDC reference: 155863
The title compound, (I), was prepared by Spa Contract Synthesis. Crystals of (I) were grown from a dimethylformamide -solution.
All H atoms were included in the refinement, at calculated positions, as riding models with C—H set to 0.95 (Ar—H), 0.98 (CH3) and 0.99 Å (CH2), except for the H atoms involved in the hydrogen-bonding interactions which were located on difference syntheses and both positional and displacement parameters refined.
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZOand 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.
C12H15ClN2OS | Dx = 1.400 Mg m−3 |
Mr = 270.77 | Melting point: 489 - 493 K K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5746 (15) Å | Cell parameters from 10172 reflections |
b = 11.878 (2) Å | θ = 1.0–27.5° |
c = 14.519 (3) Å | µ = 0.45 mm−1 |
β = 100.47 (3)° | T = 150 K |
V = 1284.6 (4) Å3 | Needle, colourless |
Z = 4 | 0.20 × 0.08 × 0.06 mm |
F(000) = 568 |
Enraf Nonius KappaCCD area-detector diffractometer | 2796 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 2125 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.2° |
ϕ and ω scans | h = −9→9 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −14→15 |
Tmin = 0.916, Tmax = 0.974 | l = −18→18 |
6971 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0691P)2 + 0.162P] where P = (Fo2 + 2Fc2)/3 |
2796 reflections | (Δ/σ)max < 0.001 |
168 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.55 e Å−3 |
C12H15ClN2OS | V = 1284.6 (4) Å3 |
Mr = 270.77 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.5746 (15) Å | µ = 0.45 mm−1 |
b = 11.878 (2) Å | T = 150 K |
c = 14.519 (3) Å | 0.20 × 0.08 × 0.06 mm |
β = 100.47 (3)° |
Enraf Nonius KappaCCD area-detector diffractometer | 2796 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 2125 reflections with I > 2σ(I) |
Tmin = 0.916, Tmax = 0.974 | Rint = 0.073 |
6971 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.40 e Å−3 |
2796 reflections | Δρmin = −0.55 e Å−3 |
168 parameters |
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) - 0.9154 (0.0059) x - 9.5063 (0.0092) y + 8.7040 (0.0135) z = 5.1034 (0.0111) * 0.0004 (0.0010) S1 * -0.0017 (0.0012) C2 * 0.0026 (0.0014) N3 * -0.0022 (0.0015) C4 * 0.0010 (0.0014) C5 Rms deviation of fitted atoms = 0.0018 - 1.0226 (0.0075) x + 8.7142 (0.0091) y + 9.8653 (0.0116) z = 11.4669 (0.0109) Angle to previous plane (with approximate e.s.d.) = 79.65 (0.07) * 0.0042 (0.0016) C7 * -0.0007 (0.0017) C8 * -0.0028 (0.0017) C9 * 0.0029 (0.0018) C10 * 0.0007 (0.0018) C11 * -0.0042 (0.0017) C12 Rms deviation of fitted atoms = 0.0030 |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.20074 (8) | 0.56421 (5) | 0.90658 (4) | 0.0323 (2) | |
S1 | 0.02394 (8) | 0.15154 (5) | 0.75439 (4) | 0.0270 (2) | |
C2 | −0.1444 (3) | 0.09324 (19) | 0.67277 (15) | 0.0240 (5) | |
N21 | −0.1131 (3) | 0.02602 (18) | 0.60550 (15) | 0.0293 (5) | |
H21 | −0.198 (4) | 0.014 (2) | 0.5597 (18) | 0.033 (7)* | |
H22 | 0.003 (4) | 0.026 (2) | 0.5980 (19) | 0.044 (8)* | |
N3 | −0.3039 (3) | 0.12351 (18) | 0.68956 (14) | 0.0261 (5) | |
H3 | −0.402 (4) | 0.098 (3) | 0.660 (2) | 0.040 (8)* | |
C4 | −0.2999 (3) | 0.1947 (2) | 0.76714 (16) | 0.0265 (5) | |
C5 | −0.1334 (3) | 0.2181 (2) | 0.81063 (16) | 0.0267 (5) | |
C6 | −0.0676 (3) | 0.2906 (2) | 0.89428 (16) | 0.0302 (6) | |
H61 | −0.1705 | 0.3123 | 0.9238 | 0.038* | |
H62 | −0.0148 | 0.3604 | 0.8736 | 0.038* | |
C7 | 0.0710 (3) | 0.2316 (2) | 0.96556 (15) | 0.0272 (5) | |
C8 | 0.2520 (3) | 0.2491 (2) | 0.96837 (16) | 0.0302 (6) | |
H8 | 0.2886 | 0.3012 | 0.9259 | 0.038* | |
C9 | 0.3825 (3) | 0.1929 (2) | 1.03128 (16) | 0.0315 (6) | |
H9 | 0.5063 | 0.2064 | 1.0317 | 0.039* | |
C10 | 0.3299 (3) | 0.1171 (2) | 1.09339 (17) | 0.0309 (6) | |
O1 | 0.4440 (3) | 0.05801 (15) | 1.16006 (13) | 0.0414 (5) | |
C11 | 0.1490 (4) | 0.0980 (2) | 1.09124 (18) | 0.0364 (6) | |
H11 | 0.1125 | 0.0459 | 1.1337 | 0.045* | |
C12 | 0.0218 (4) | 0.1539 (2) | 1.02825 (18) | 0.0346 (6) | |
H12 | −0.1018 | 0.1393 | 1.0274 | 0.043* | |
C13 | −0.4737 (3) | 0.2328 (2) | 0.79016 (18) | 0.0364 (6) | |
H131 | −0.5296 | 0.1706 | 0.8186 | 0.046* | |
H132 | −0.5536 | 0.2571 | 0.7327 | 0.046* | |
H133 | −0.4525 | 0.2959 | 0.8343 | 0.046* | |
C14 | 0.6315 (4) | 0.0671 (3) | 1.1596 (2) | 0.0446 (7) | |
H141 | 0.6593 | 0.0294 | 1.1039 | 0.056* | |
H142 | 0.6992 | 0.0314 | 1.2159 | 0.056* | |
H143 | 0.6649 | 0.1467 | 1.1585 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0237 (3) | 0.0452 (4) | 0.0281 (3) | 0.0040 (3) | 0.0048 (2) | 0.0053 (3) |
S1 | 0.0204 (3) | 0.0343 (4) | 0.0261 (3) | 0.0002 (2) | 0.0039 (2) | −0.0042 (2) |
C2 | 0.0217 (12) | 0.0260 (12) | 0.0248 (12) | −0.0010 (10) | 0.0056 (9) | 0.0029 (9) |
N21 | 0.0242 (12) | 0.0387 (13) | 0.0256 (11) | −0.0035 (10) | 0.0060 (9) | −0.0064 (9) |
N3 | 0.0194 (10) | 0.0348 (11) | 0.0239 (10) | 0.0005 (9) | 0.0037 (8) | −0.0014 (9) |
C4 | 0.0258 (12) | 0.0302 (13) | 0.0243 (12) | −0.0013 (10) | 0.0067 (9) | −0.0002 (10) |
C5 | 0.0256 (12) | 0.0292 (13) | 0.0265 (12) | 0.0007 (10) | 0.0074 (9) | 0.0009 (10) |
C6 | 0.0281 (13) | 0.0342 (14) | 0.0281 (12) | 0.0012 (11) | 0.0044 (10) | −0.0051 (10) |
C7 | 0.0286 (13) | 0.0302 (13) | 0.0233 (12) | 0.0003 (10) | 0.0059 (9) | −0.0059 (10) |
C8 | 0.0304 (13) | 0.0353 (14) | 0.0257 (12) | −0.0027 (11) | 0.0073 (10) | −0.0011 (10) |
C9 | 0.0253 (13) | 0.0397 (14) | 0.0307 (13) | −0.0018 (11) | 0.0080 (10) | −0.0036 (11) |
C10 | 0.0334 (14) | 0.0315 (13) | 0.0267 (12) | −0.0003 (11) | 0.0027 (10) | −0.0035 (10) |
O1 | 0.0364 (11) | 0.0451 (11) | 0.0412 (11) | 0.0050 (9) | 0.0029 (8) | 0.0116 (9) |
C11 | 0.0378 (15) | 0.0368 (15) | 0.0353 (14) | −0.0065 (12) | 0.0089 (12) | 0.0048 (12) |
C12 | 0.0284 (14) | 0.0414 (16) | 0.0344 (14) | −0.0052 (12) | 0.0069 (11) | −0.0019 (11) |
C13 | 0.0257 (13) | 0.0481 (16) | 0.0373 (14) | 0.0004 (12) | 0.0106 (11) | −0.0074 (12) |
C14 | 0.0371 (16) | 0.0478 (18) | 0.0460 (16) | 0.0068 (13) | −0.0002 (13) | 0.0042 (13) |
S1—C2 | 1.721 (2) | C8—C9 | 1.388 (3) |
S1—C5 | 1.751 (2) | C8—H8 | 0.9500 |
C2—N21 | 1.316 (3) | C9—C10 | 1.383 (4) |
C2—N3 | 1.324 (3) | C9—H9 | 0.9500 |
N21—H21 | 0.85 (3) | C10—O1 | 1.368 (3) |
N21—H22 | 0.91 (3) | C10—C11 | 1.384 (4) |
N3—C4 | 1.404 (3) | O1—C14 | 1.426 (3) |
N3—H3 | 0.84 (3) | C11—C12 | 1.373 (4) |
C4—C5 | 1.333 (3) | C11—H11 | 0.9500 |
C4—C13 | 1.487 (3) | C12—H12 | 0.9500 |
C5—C6 | 1.499 (3) | C13—H131 | 0.9800 |
C6—C7 | 1.507 (3) | C13—H132 | 0.9800 |
C6—H61 | 0.9900 | C13—H133 | 0.9800 |
C6—H62 | 0.9900 | C14—H141 | 0.9800 |
C7—C8 | 1.380 (3) | C14—H142 | 0.9800 |
C7—C12 | 1.394 (3) | C14—H143 | 0.9800 |
C2—S1—C5 | 91.19 (11) | C9—C8—H8 | 118.9 |
N21—C2—N3 | 126.5 (2) | C10—C9—C8 | 119.1 (2) |
N21—C2—S1 | 122.97 (19) | C10—C9—H9 | 120.4 |
N3—C2—S1 | 110.52 (17) | C8—C9—H9 | 120.4 |
C2—N21—H21 | 118.4 (18) | O1—C10—C11 | 115.3 (2) |
C2—N21—H22 | 113.4 (18) | O1—C10—C9 | 125.1 (2) |
H21—N21—H22 | 121 (3) | C11—C10—C9 | 119.5 (2) |
C2—N3—C4 | 115.1 (2) | C10—O1—C14 | 117.3 (2) |
C2—N3—H3 | 124 (2) | C12—C11—C10 | 120.6 (2) |
C4—N3—H3 | 120 (2) | C12—C11—H11 | 119.7 |
C5—C4—N3 | 112.7 (2) | C10—C11—H11 | 119.7 |
C5—C4—C13 | 129.1 (2) | C11—C12—C7 | 121.1 (2) |
N3—C4—C13 | 118.2 (2) | C11—C12—H12 | 119.5 |
C4—C5—C6 | 130.6 (2) | C7—C12—H12 | 119.5 |
C4—C5—S1 | 110.50 (18) | C4—C13—H131 | 109.5 |
C6—C5—S1 | 118.88 (17) | C4—C13—H132 | 109.5 |
C5—C6—C7 | 112.1 (2) | H131—C13—H132 | 109.5 |
C5—C6—H61 | 109.2 | C4—C13—H133 | 109.5 |
C7—C6—H61 | 109.2 | H131—C13—H133 | 109.5 |
C5—C6—H62 | 109.2 | H132—C13—H133 | 109.5 |
C7—C6—H62 | 109.2 | O1—C14—H141 | 109.5 |
H61—C6—H62 | 107.9 | O1—C14—H142 | 109.5 |
C8—C7—C12 | 117.5 (2) | H141—C14—H142 | 109.5 |
C8—C7—C6 | 121.0 (2) | O1—C14—H143 | 109.5 |
C12—C7—C6 | 121.4 (2) | H141—C14—H143 | 109.5 |
C7—C8—C9 | 122.1 (2) | H142—C14—H143 | 109.5 |
C7—C8—H8 | 118.9 | ||
C5—S1—C2—N21 | −178.6 (2) | C5—C6—C7—C8 | 97.2 (3) |
C5—S1—C2—N3 | −0.21 (18) | C5—C6—C7—C12 | −80.0 (3) |
N21—C2—N3—C4 | 178.8 (2) | C12—C7—C8—C9 | −0.5 (4) |
S1—C2—N3—C4 | 0.5 (3) | C6—C7—C8—C9 | −177.8 (2) |
C2—N3—C4—C5 | −0.5 (3) | C7—C8—C9—C10 | −0.1 (4) |
C2—N3—C4—C13 | 179.7 (2) | C8—C9—C10—O1 | −178.6 (2) |
N3—C4—C5—C6 | 179.1 (2) | C8—C9—C10—C11 | 0.5 (4) |
C13—C4—C5—C6 | −1.2 (5) | C11—C10—O1—C14 | 174.5 (2) |
N3—C4—C5—S1 | 0.3 (3) | C9—C10—O1—C14 | −6.4 (4) |
C13—C4—C5—S1 | −179.9 (2) | O1—C10—C11—C12 | 179.0 (2) |
C2—S1—C5—C4 | −0.09 (19) | C9—C10—C11—C12 | −0.1 (4) |
C2—S1—C5—C6 | −179.0 (2) | C10—C11—C12—C7 | −0.5 (4) |
C4—C5—C6—C7 | 131.3 (3) | C8—C7—C12—C11 | 0.9 (4) |
S1—C5—C6—C7 | −50.1 (3) | C6—C7—C12—C11 | 178.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···Cl1i | 0.84 (3) | 2.33 (3) | 3.155 (2) | 167 (3) |
N21—H21···Cl1ii | 0.85 (3) | 2.40 (3) | 3.162 (2) | 150 (2) |
N21—H22···Cl1iii | 0.91 (3) | 2.30 (3) | 3.193 (2) | 168 (3) |
Symmetry codes: (i) −x−1/2, y−1/2, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1/2, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C12H15ClN2OS |
Mr | 270.77 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 150 |
a, b, c (Å) | 7.5746 (15), 11.878 (2), 14.519 (3) |
β (°) | 100.47 (3) |
V (Å3) | 1284.6 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.45 |
Crystal size (mm) | 0.20 × 0.08 × 0.06 |
Data collection | |
Diffractometer | Enraf Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.916, 0.974 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6971, 2796, 2125 |
Rint | 0.073 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.136, 1.01 |
No. of reflections | 2796 |
No. of parameters | 168 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.40, −0.55 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, DENZOand COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···Cl1i | 0.84 (3) | 2.33 (3) | 3.155 (2) | 167 (3) |
N21—H21···Cl1ii | 0.85 (3) | 2.40 (3) | 3.162 (2) | 150 (2) |
N21—H22···Cl1iii | 0.91 (3) | 2.30 (3) | 3.193 (2) | 168 (3) |
Symmetry codes: (i) −x−1/2, y−1/2, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1/2, y−1/2, −z+3/2. |
NO COMMENT