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The crystal structure of the title thiobenzamide, C17H17NS, was determined to investigate the relationship between the photoreactivity in solid state and the structure. The geometry was confirmed to be the Z isomer.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100004042/qa0253sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S0108270100004042/qa0253Isup2.hkl |
CCDC reference: 144713
S1. Experimental top
The title compound, (I), was prepared by one of the authors (HA) in a study on photocyclization of enamides and thioamides in the solid state (Aoyama, 2000). Crystals were grown from a benzene solution.
S2. Refinement top
All H-atom positional parameters were calculated geometrically and fixed with Uiso(H) = 1.2Ueq(parent atom).
Computing details top
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN.
N-Methyl-N-{(Z)-2-phenyl-propenyl}-thiobenzamide top
Crystal data top
| C17H17NS | Dx = 1.197 Mg m−3 |
| Mr = 267.39 | Mo Kα radiation, λ = 0.71073 Å |
| Monoclinic, P21/c | Cell parameters from 25 reflections |
| a = 10.057 (3) Å | θ = 14.3–15.0° |
| b = 8.344 (3) Å | µ = 0.20 mm−1 |
| c = 17.962 (4) Å | T = 298 K |
| β = 100.13 (2)° | Prism, yellow |
| V = 1483.8 (7) Å3 | 0.6 × 0.6 × 0.3 mm |
| Z = 4 |
Data collection top
| Rigaku AFC-7R diffractometer | θmax = 27.5°, θmin = 2.5° |
| θ–2θ scans | h = −13→0 |
| 3585 measured reflections | k = 0→10 |
| 3396 independent reflections | l = −23→23 |
| 2232 reflections with I > 2σ(I) | 3 standard reflections every 150 reflections |
| Rint = 0.027 | intensity decay: none |
Refinement top
| Refinement on F2 | H-atom parameters not refined |
| R[F2 > 2σ(F2)] = 0.066 | w = 1/[σ2(Fo2) + (0.05P)2 + 2.P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.175 | (Δ/σ)max = 0.001 |
| S = 1.02 | Δρmax = 0.48 e Å−3 |
| 3396 reflections | Δρmin = −0.40 e Å−3 |
| 172 parameters |
Crystal data top
| C17H17NS | V = 1483.8 (7) Å3 |
| Mr = 267.39 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 10.057 (3) Å | µ = 0.20 mm−1 |
| b = 8.344 (3) Å | T = 298 K |
| c = 17.962 (4) Å | 0.6 × 0.6 × 0.3 mm |
| β = 100.13 (2)° |
Data collection top
| Rigaku AFC-7R diffractometer | Rint = 0.027 |
| 3585 measured reflections | 3 standard reflections every 150 reflections |
| 3396 independent reflections | intensity decay: none |
| 2232 reflections with I > 2σ(I) |
Refinement top
| R[F2 > 2σ(F2)] = 0.066 | 172 parameters |
| wR(F2) = 0.175 | H-atom parameters not refined |
| S = 1.02 | Δρmax = 0.48 e Å−3 |
| 3396 reflections | Δρmin = −0.40 e Å−3 |
Special details top
Refinement. Refinement was based on F2 against all reflections. The weighted R-factor (wR) and goodness of fit (S) were based on F2, and conventional R-factor (R) was calculated on F, with F set to zero for negative F2. The threshold expression of I > 2σ(I) was used only for calculating R-factor(gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.36998 (9) | 0.0798 (1) | 0.32730 (5) | 0.0652 (3) | |
| N2 | 0.3475 (3) | 0.3937 (3) | 0.3389 (1) | 0.0516 (6) | |
| C3 | 0.2871 (3) | 0.2487 (3) | 0.3368 (2) | 0.0465 (7) | |
| C4 | 0.1416 (3) | 0.2435 (3) | 0.3400 (2) | 0.0445 (6) | |
| C5 | 0.0916 (3) | 0.1378 (3) | 0.3882 (2) | 0.0525 (7) | |
| C6 | −0.0441 (4) | 0.1243 (4) | 0.3875 (2) | 0.0661 (9) | |
| C7 | −0.1342 (4) | 0.2148 (5) | 0.3388 (3) | 0.077 (1) | |
| C8 | −0.0875 (4) | 0.3209 (5) | 0.2903 (2) | 0.075 (1) | |
| C9 | 0.0495 (4) | 0.3369 (4) | 0.2909 (2) | 0.0598 (8) | |
| C10 | 0.4837 (4) | 0.4098 (5) | 0.3225 (2) | 0.077 (1) | |
| C11 | 0.2951 (3) | 0.5356 (3) | 0.3674 (2) | 0.0542 (8) | |
| C12 | 0.2633 (3) | 0.5562 (3) | 0.4355 (2) | 0.0489 (7) | |
| C13 | 0.2085 (4) | 0.7181 (4) | 0.4528 (2) | 0.075 (1) | |
| C14 | 0.2781 (3) | 0.4334 (3) | 0.4960 (2) | 0.0459 (6) | |
| C15 | 0.3839 (3) | 0.3237 (4) | 0.5062 (2) | 0.0549 (8) | |
| C16 | 0.3951 (4) | 0.2093 (4) | 0.5631 (2) | 0.072 (1) | |
| C17 | 0.3041 (5) | 0.2045 (5) | 0.6110 (2) | 0.080 (1) | |
| C18 | 0.2006 (5) | 0.3151 (6) | 0.6036 (2) | 0.081 (1) | |
| C19 | 0.1883 (4) | 0.4290 (4) | 0.5468 (2) | 0.0621 (8) | |
| H5 | 0.1539 | 0.0720 | 0.4228 | 0.0600* | |
| H6 | −0.0772 | 0.0498 | 0.4210 | 0.0802* | |
| H7 | −0.2312 | 0.2059 | 0.3382 | 0.0856* | |
| H8 | −0.1519 | 0.3845 | 0.2555 | 0.0894* | |
| H9 | 0.0821 | 0.4123 | 0.2576 | 0.0683* | |
| H10A | 0.5124 | 0.3116 | 0.3030 | 0.0907* | |
| H10B | 0.4842 | 0.4935 | 0.2848 | 0.0907* | |
| H10C | 0.5450 | 0.4399 | 0.3674 | 0.0907* | |
| H11 | 0.2808 | 0.6266 | 0.3338 | 0.0613* | |
| H13A | 0.2718 | 0.7997 | 0.4491 | 0.0894* | |
| H13B | 0.1249 | 0.7385 | 0.4187 | 0.0894* | |
| H13C | 0.1886 | 0.7158 | 0.5041 | 0.0894* | |
| H15 | 0.4501 | 0.3270 | 0.4731 | 0.0641* | |
| H16 | 0.4673 | 0.1311 | 0.5686 | 0.0840* | |
| H17 | 0.3102 | 0.1222 | 0.6502 | 0.0902* | |
| H18 | 0.1387 | 0.3143 | 0.6398 | 0.0951* | |
| H19 | 0.1140 | 0.5069 | 0.5417 | 0.0741* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0645 (5) | 0.0557 (5) | 0.0733 (6) | 0.0130 (4) | 0.0067 (4) | −0.0111 (4) |
| N2 | 0.060 (2) | 0.049 (1) | 0.045 (1) | −0.007 (1) | 0.008 (1) | 0.000 (1) |
| C3 | 0.056 (2) | 0.044 (2) | 0.037 (1) | 0.001 (1) | 0.001 (1) | 0.000 (1) |
| C4 | 0.054 (2) | 0.032 (1) | 0.044 (1) | 0.003 (1) | 0.000 (1) | −0.004 (1) |
| C5 | 0.063 (2) | 0.035 (1) | 0.057 (2) | 0.001 (1) | 0.007 (1) | −0.001 (1) |
| C6 | 0.067 (2) | 0.055 (2) | 0.080 (2) | −0.011 (2) | 0.020 (2) | −0.015 (2) |
| C7 | 0.052 (2) | 0.080 (3) | 0.097 (3) | −0.003 (2) | 0.009 (2) | −0.033 (2) |
| C8 | 0.064 (2) | 0.069 (2) | 0.082 (3) | 0.020 (2) | −0.014 (2) | −0.015 (2) |
| C9 | 0.070 (2) | 0.046 (2) | 0.056 (2) | 0.010 (2) | −0.007 (2) | 0.001 (1) |
| C10 | 0.080 (3) | 0.087 (3) | 0.070 (2) | −0.025 (2) | 0.028 (2) | −0.012 (2) |
| C11 | 0.069 (2) | 0.034 (1) | 0.056 (2) | −0.004 (1) | 0.001 (1) | 0.009 (1) |
| C12 | 0.056 (2) | 0.030 (1) | 0.058 (2) | −0.002 (1) | 0.002 (1) | −0.001 (1) |
| C13 | 0.099 (3) | 0.037 (2) | 0.086 (3) | 0.007 (2) | 0.008 (2) | −0.001 (2) |
| C14 | 0.053 (2) | 0.037 (1) | 0.044 (1) | −0.006 (1) | −0.002 (1) | −0.005 (1) |
| C15 | 0.061 (2) | 0.048 (2) | 0.050 (2) | −0.002 (1) | −0.004 (1) | 0.001 (1) |
| C16 | 0.087 (3) | 0.051 (2) | 0.066 (2) | −0.001 (2) | −0.020 (2) | 0.011 (2) |
| C17 | 0.104 (3) | 0.071 (2) | 0.056 (2) | −0.026 (2) | −0.012 (2) | 0.020 (2) |
| C18 | 0.092 (3) | 0.092 (3) | 0.060 (2) | −0.031 (3) | 0.013 (2) | 0.004 (2) |
| C19 | 0.063 (2) | 0.060 (2) | 0.063 (2) | −0.011 (2) | 0.009 (2) | −0.005 (2) |
Geometric parameters (Å, º) top
| S1—C3 | 1.661 (3) | C11—C12 | 1.327 (5) |
| N2—C3 | 1.351 (4) | C11—H11 | 0.97 |
| N2—C10 | 1.456 (5) | C12—C13 | 1.512 (5) |
| N2—C11 | 1.428 (4) | C12—C14 | 1.483 (4) |
| C3—C4 | 1.475 (4) | C13—H13A | 0.94 |
| C4—C5 | 1.390 (4) | C13—H13B | 0.96 |
| C4—C9 | 1.398 (4) | C13—H13C | 0.98 |
| C5—C6 | 1.367 (5) | C14—C15 | 1.391 (4) |
| C5—H5 | 0.97 | C14—C19 | 1.392 (5) |
| C6—C7 | 1.370 (5) | C15—C16 | 1.389 (5) |
| C6—H6 | 0.96 | C15—H15 | 0.97 |
| C7—C8 | 1.381 (6) | C16—C17 | 1.362 (7) |
| C7—H7 | 0.98 | C16—H16 | 0.97 |
| C8—C9 | 1.382 (5) | C17—C18 | 1.380 (7) |
| C8—H8 | 0.97 | C17—H17 | 0.98 |
| C9—H9 | 0.97 | C18—C19 | 1.385 (6) |
| C10—H10A | 0.96 | C18—H18 | 0.98 |
| C10—H10B | 0.97 | C19—H19 | 0.98 |
| C10—H10C | 0.96 | ||
| C3—N2—C10 | 120.8 (3) | N2—C11—C12 | 127.0 (3) |
| C3—N2—C11 | 124.0 (3) | N2—C11—H11 | 117 |
| C10—N2—C11 | 114.6 (3) | C12—C11—H11 | 116 |
| S1—C3—N2 | 122.0 (2) | C11—C12—C13 | 117.5 (3) |
| S1—C3—C4 | 119.8 (2) | C11—C12—C14 | 125.2 (3) |
| N2—C3—C4 | 118.1 (3) | C13—C12—C14 | 117.3 (3) |
| C3—C4—C5 | 120.9 (2) | C12—C13—H13A | 111 |
| C3—C4—C9 | 120.7 (3) | C12—C13—H13B | 110 |
| C5—C4—C9 | 118.3 (3) | C12—C13—H13C | 109 |
| C4—C5—C6 | 121.1 (3) | H13A—C13—H13B | 111 |
| C4—C5—H5 | 120 | H13A—C13—H13C | 109 |
| C6—C5—H5 | 119 | H13B—C13—H13C | 108 |
| C5—C6—C7 | 120.4 (4) | C12—C14—C15 | 121.8 (3) |
| C5—C6—H6 | 120 | C12—C14—C19 | 120.4 (3) |
| C7—C6—H6 | 119 | C15—C14—C19 | 117.8 (3) |
| C6—C7—C8 | 119.8 (4) | C14—C15—C16 | 120.7 (3) |
| C6—C7—H7 | 121 | C14—C15—H15 | 120 |
| C8—C7—H7 | 120 | C16—C15—H15 | 120 |
| C7—C8—C9 | 120.4 (3) | C15—C16—C17 | 120.5 (4) |
| C7—C8—H8 | 120 | C15—C16—H16 | 120 |
| C9—C8—H8 | 120 | C17—C16—H16 | 120 |
| C4—C9—C8 | 120.0 (3) | C16—C17—C18 | 120.0 (4) |
| C4—C9—H9 | 120 | C16—C17—H17 | 121 |
| C8—C9—H9 | 120 | C18—C17—H17 | 119 |
| N2—C10—H10A | 111 | C17—C18—C19 | 119.8 (4) |
| N2—C10—H10B | 109 | C17—C18—H18 | 119 |
| N2—C10—H10C | 110 | C19—C18—H18 | 121 |
| H10A—C10—H10B | 109 | C14—C19—C18 | 121 |
| H10A—C10—H10C | 110 | C14—C19—H19 | 120 |
| H10B—C10—H10C | 109 | C18—C19—H19 | 119 |
Experimental details
| Crystal data | |
| Chemical formula | C17H17NS |
| Mr | 267.39 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 298 |
| a, b, c (Å) | 10.057 (3), 8.344 (3), 17.962 (4) |
| β (°) | 100.13 (2) |
| V (Å3) | 1483.8 (7) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.20 |
| Crystal size (mm) | 0.6 × 0.6 × 0.3 |
| Data collection | |
| Diffractometer | Rigaku AFC-7R diffractometer |
| Absorption correction | – |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 3585, 3396, 2232 |
| Rint | 0.027 |
| (sin θ/λ)max (Å−1) | 0.650 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.175, 1.02 |
| No. of reflections | 3396 |
| No. of parameters | 172 |
| No. of restraints | ? |
| H-atom treatment | H-atom parameters not refined |
| Δρmax, Δρmin (e Å−3) | 0.48, −0.40 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1999), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), TEXSAN.
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