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The title compound, C
14H
15ClN
2OS, was prepared from a condensation reaction between 2-(4-chlorophenyl)-3-methylbutanoyl chloride and 2-aminothiazole. The angle between the thiazole and benzene rings is 58.87 (8)°. There are N—H
N hydrogen-bonding interactions which give rise to dimers in the solid state.
Supporting information
CCDC reference: 628050
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.098
- Data-to-parameter ratio = 19.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT734_ALERT_1_B Contact Calc 3.525(2), Rep 3.5251(4) ...... 5.00 su-Ra
S1 -S1 1.555 2.654
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C6 - C7 .. 6.00 su
PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003);; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
2-(4-Chlorophenyl)-3-methyl-
N-(thiazol-2-yl)butanamide
top
Crystal data top
C14H15ClN2OS | F(000) = 1232.00 |
Mr = 294.80 | Dx = 1.321 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -C 2yc | Cell parameters from 10387 reflections |
a = 14.925 (6) Å | θ = 3.2–27.5° |
b = 17.712 (10) Å | µ = 0.39 mm−1 |
c = 11.214 (4) Å | T = 298 K |
β = 91.497 (14)° | Needle, colourless |
V = 2963 (2) Å3 | 0.39 × 0.32 × 0.28 mm |
Z = 8 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2063 reflections with F2 > 2.0σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.031 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −19→19 |
Tmin = 0.863, Tmax = 0.896 | k = −22→22 |
14487 measured reflections | l = −14→13 |
3382 independent reflections | |
Refinement top
Refinement on F2 | w = 1/[0.0004Fo2 + σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.038 | (Δ/σ)max < 0.001 |
wR(F2) = 0.098 | Δρmax = 0.27 e Å−3 |
S = 1.01 | Δρmin = −0.30 e Å−3 |
3382 reflections | Extinction correction: Larson (1970), eq. 22 |
173 parameters | Extinction coefficient: 62 (17) |
H-atom parameters constrained | |
Special details top
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and
goodness of fit (S) are based on F2. R-factor (gt) are
based on F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.02854 (4) | −0.18695 (4) | 0.07038 (6) | 0.1057 (2) | |
S1 | 0.49072 (3) | 0.10968 (3) | −0.09363 (3) | 0.06327 (15) | |
O1 | 0.31766 (6) | 0.09566 (8) | −0.03684 (9) | 0.0671 (4) | |
N1 | 0.56881 (8) | 0.10153 (9) | 0.11245 (11) | 0.0552 (4) | |
N2 | 0.41237 (8) | 0.09527 (8) | 0.12263 (10) | 0.0499 (4) | |
C1 | 0.63402 (11) | 0.10903 (12) | 0.02852 (14) | 0.0662 (5) | |
C2 | 0.60501 (11) | 0.11407 (12) | −0.08444 (14) | 0.0691 (6) | |
C3 | 0.49024 (10) | 0.10126 (10) | 0.05887 (12) | 0.0460 (4) | |
C4 | 0.32915 (10) | 0.09375 (10) | 0.07116 (12) | 0.0506 (4) | |
C5 | 0.25170 (10) | 0.09162 (10) | 0.15649 (12) | 0.0497 (4) | |
C6 | 0.19969 (11) | 0.16629 (11) | 0.14601 (14) | 0.0568 (5) | |
C7 | 0.26035 (13) | 0.23379 (12) | 0.17026 (18) | 0.0784 (7) | |
C8 | 0.12099 (12) | 0.16759 (12) | 0.22941 (19) | 0.0812 (7) | |
C9 | 0.19540 (9) | 0.02216 (10) | 0.13468 (12) | 0.0473 (4) | |
C10 | 0.19315 (11) | −0.03496 (12) | 0.21785 (13) | 0.0578 (5) | |
C11 | 0.14208 (12) | −0.09857 (12) | 0.19990 (17) | 0.0686 (6) | |
C12 | 0.09282 (12) | −0.10628 (12) | 0.09502 (18) | 0.0645 (6) | |
C13 | 0.09383 (12) | −0.05083 (12) | 0.01060 (16) | 0.0631 (6) | |
C14 | 0.14415 (10) | 0.01307 (11) | 0.03022 (13) | 0.0552 (5) | |
H1 | 0.6947 | 0.1105 | 0.0495 | 0.079* | |
H2 | 0.6419 | 0.1193 | −0.1495 | 0.083* | |
H5 | 0.2772 | 0.0884 | 0.2378 | 0.060* | |
H6 | 0.1758 | 0.1705 | 0.0640 | 0.068* | |
H10 | 0.2272 | −0.0303 | 0.2881 | 0.069* | |
H11 | 0.1407 | −0.1361 | 0.2579 | 0.082* | |
H13 | 0.0605 | −0.0563 | −0.0601 | 0.076* | |
H14 | 0.1440 | 0.0509 | −0.0273 | 0.066* | |
H71 | 0.3097 | 0.2325 | 0.1171 | 0.094* | |
H72 | 0.2827 | 0.2320 | 0.2513 | 0.094* | |
H73 | 0.2270 | 0.2796 | 0.1577 | 0.094* | |
H81 | 0.0863 | 0.2125 | 0.2153 | 0.097* | |
H82 | 0.1430 | 0.1671 | 0.3106 | 0.097* | |
H83 | 0.0840 | 0.1240 | 0.2149 | 0.097* | |
H201 | 0.4170 | 0.0924 | 0.1991 | 0.060* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.1118 (5) | 0.0736 (4) | 0.1320 (5) | −0.0245 (3) | 0.0097 (4) | −0.0192 (3) |
S1 | 0.0515 (2) | 0.1014 (4) | 0.0370 (2) | 0.0032 (2) | 0.00220 (18) | 0.0027 (2) |
O1 | 0.0457 (6) | 0.1180 (12) | 0.0374 (5) | −0.0056 (6) | −0.0038 (4) | 0.0025 (6) |
N1 | 0.0392 (6) | 0.0846 (12) | 0.0415 (6) | 0.0007 (7) | 0.0002 (5) | 0.0016 (6) |
N2 | 0.0389 (6) | 0.0762 (11) | 0.0345 (5) | −0.0028 (6) | −0.0008 (5) | 0.0016 (6) |
C1 | 0.0371 (8) | 0.1064 (17) | 0.0553 (9) | 0.0030 (9) | 0.0049 (7) | 0.0043 (10) |
C2 | 0.0509 (9) | 0.1073 (18) | 0.0498 (9) | 0.0042 (10) | 0.0127 (7) | 0.0059 (10) |
C3 | 0.0435 (8) | 0.0564 (11) | 0.0381 (7) | 0.0001 (7) | −0.0009 (6) | 0.0002 (7) |
C4 | 0.0417 (8) | 0.0704 (13) | 0.0394 (7) | −0.0031 (8) | −0.0025 (6) | 0.0012 (7) |
C5 | 0.0402 (8) | 0.0735 (14) | 0.0352 (7) | −0.0029 (8) | −0.0024 (6) | 0.0019 (7) |
C6 | 0.0497 (9) | 0.0674 (14) | 0.0530 (9) | −0.0029 (9) | −0.0003 (7) | 0.0003 (8) |
C7 | 0.0824 (13) | 0.0727 (17) | 0.0800 (13) | −0.0085 (11) | 0.0018 (10) | 0.0010 (11) |
C8 | 0.0675 (12) | 0.0824 (18) | 0.0946 (14) | 0.0074 (11) | 0.0234 (10) | −0.0067 (12) |
C9 | 0.0372 (7) | 0.0654 (12) | 0.0394 (7) | 0.0043 (7) | 0.0020 (6) | 0.0018 (7) |
C10 | 0.0546 (10) | 0.0718 (14) | 0.0468 (8) | 0.0074 (9) | −0.0021 (7) | 0.0054 (8) |
C11 | 0.0739 (12) | 0.0626 (14) | 0.0696 (11) | 0.0066 (11) | 0.0085 (9) | 0.0121 (10) |
C12 | 0.0575 (10) | 0.0614 (14) | 0.0751 (12) | −0.0001 (9) | 0.0078 (9) | −0.0099 (10) |
C13 | 0.0550 (10) | 0.0750 (16) | 0.0591 (10) | 0.0001 (10) | −0.0051 (8) | −0.0107 (10) |
C14 | 0.0487 (8) | 0.0707 (14) | 0.0459 (8) | 0.0007 (9) | −0.0045 (7) | 0.0041 (8) |
Geometric parameters (Å, º) top
Cl1—C12 | 1.739 (2) | C12—C13 | 1.364 (2) |
S1—C2 | 1.7079 (17) | C13—C14 | 1.373 (2) |
S1—C3 | 1.7168 (15) | N2—H201 | 0.860 |
O1—C4 | 1.2192 (17) | C1—H1 | 0.930 |
N1—C1 | 1.378 (2) | C2—H2 | 0.930 |
N1—C3 | 1.3036 (18) | C5—H5 | 0.980 |
N2—C3 | 1.3844 (19) | C6—H6 | 0.980 |
N2—C4 | 1.3561 (18) | C7—H71 | 0.960 |
C1—C2 | 1.331 (2) | C7—H72 | 0.960 |
C4—C5 | 1.520 (2) | C7—H73 | 0.960 |
C5—C6 | 1.536 (2) | C8—H81 | 0.960 |
C5—C9 | 1.506 (2) | C8—H82 | 0.960 |
C6—C7 | 1.520 (2) | C8—H83 | 0.960 |
C6—C8 | 1.521 (2) | C10—H10 | 0.930 |
C9—C10 | 1.377 (2) | C11—H11 | 0.930 |
C9—C14 | 1.392 (2) | C13—H13 | 0.930 |
C10—C11 | 1.372 (2) | C14—H14 | 0.930 |
C11—C12 | 1.377 (2) | | |
| | | |
S1···S1i | 3.5251 (4) | H10···O1vi | 2.623 |
O1···C7ii | 3.554 (2) | H10···C13vi | 3.537 |
O1···C10iii | 3.4510 (19) | H10···C14vi | 3.029 |
N1···N2iv | 2.9788 (16) | H10···H1iv | 3.283 |
N2···N1iv | 2.9788 (16) | H10···H2x | 2.979 |
C7···O1ii | 3.554 (2) | H10···H13vi | 3.415 |
C7···C11v | 3.598 (3) | H10···H14vi | 2.469 |
C10···O1vi | 3.4510 (19) | H10···H73vii | 3.487 |
C11···C7vii | 3.598 (3) | H11···Cl1ix | 3.340 |
C13···C13viii | 3.333 (2) | H11···O1vi | 3.531 |
Cl1···H6viii | 3.379 | H11···C7vii | 2.843 |
Cl1···H11ix | 3.340 | H11···H2x | 3.506 |
Cl1···H14viii | 3.550 | H11···H6vi | 3.513 |
Cl1···H82iii | 3.433 | H11···H14vi | 2.841 |
S1···H2i | 3.457 | H11···H71vii | 2.807 |
O1···H10iii | 2.623 | H11···H72vii | 2.605 |
O1···H11iii | 3.531 | H11···H73vii | 2.633 |
O1···H73ii | 2.668 | H13···C8iii | 3.222 |
N1···H5iv | 2.821 | H13···C13viii | 3.046 |
N1···H72iv | 3.523 | H13···C14viii | 3.175 |
N1···H201iv | 2.125 | H13···H10iii | 3.415 |
N2···H201iv | 3.196 | H13···H13viii | 3.030 |
C1···H5iv | 2.929 | H13···H14viii | 3.231 |
C1···H72iv | 3.496 | H13···H82iii | 2.749 |
C1···H201iv | 3.181 | H13···H83viii | 2.985 |
C3···H201iv | 3.018 | H13···H83iii | 2.824 |
C4···H73ii | 3.494 | H14···Cl1viii | 3.550 |
C5···H1iv | 3.388 | H14···C10iii | 2.983 |
C6···H71ii | 3.453 | H14···C11iii | 3.173 |
C7···H6ii | 3.288 | H14···C13viii | 3.559 |
C7···H11v | 2.843 | H14···H10iii | 2.469 |
C7···H71ii | 3.415 | H14···H11iii | 2.841 |
C8···H13vi | 3.222 | H14···H13viii | 3.231 |
C8···H81ix | 3.269 | H71···C6ii | 3.453 |
C8···H83ix | 3.232 | H71···C7ii | 3.415 |
C9···H1x | 3.557 | H71···H6ii | 2.674 |
C9···H2x | 3.489 | H71···H11v | 2.807 |
C10···H2x | 2.996 | H71···H71ii | 3.197 |
C10···H14vi | 2.983 | H71···H73ii | 3.123 |
C11···H2x | 3.308 | H72···N1iv | 3.523 |
C11···H14vi | 3.173 | H72···C1iv | 3.496 |
C11···H72vii | 3.246 | H72···C11v | 3.246 |
C11···H73vii | 3.297 | H72···H1iv | 3.113 |
C12···H82iii | 3.466 | H72···H2xii | 3.566 |
C13···H1x | 3.413 | H72···H11v | 2.605 |
C13···H10iii | 3.537 | H73···O1ii | 2.668 |
C13···H13viii | 3.046 | H73···C4ii | 3.494 |
C13···H14viii | 3.559 | H73···C11v | 3.297 |
C13···H82iii | 3.145 | H73···H2xii | 3.105 |
C13···H83iii | 3.560 | H73···H6ii | 3.043 |
C14···H1x | 3.389 | H73···H10v | 3.487 |
C14···H10iii | 3.029 | H73···H11v | 2.633 |
C14···H13viii | 3.175 | H73···H71ii | 3.123 |
H1···C5iv | 3.388 | H81···C8ix | 3.269 |
H1···C9x | 3.557 | H81···H2xii | 3.435 |
H1···C13x | 3.413 | H81···H81ix | 2.710 |
H1···C14x | 3.389 | H81···H82ix | 3.520 |
H1···H5iv | 2.442 | H81···H83ix | 3.104 |
H1···H10iv | 3.283 | H82···Cl1vi | 3.433 |
H1···H72iv | 3.113 | H82···C12vi | 3.466 |
H1···H82iv | 3.023 | H82···C13vi | 3.145 |
H1···H201iv | 3.328 | H82···H1iv | 3.023 |
H2···S1i | 3.457 | H82···H13vi | 2.749 |
H2···C9x | 3.489 | H82···H81ix | 3.520 |
H2···C10x | 2.996 | H82···H83ix | 3.477 |
H2···C11x | 3.308 | H83···C8ix | 3.232 |
H2···H10x | 2.979 | H83···C13vi | 3.560 |
H2···H11x | 3.506 | H83···H13viii | 2.985 |
H2···H72xi | 3.566 | H83···H13vi | 2.824 |
H2···H73xi | 3.105 | H83···H81ix | 3.104 |
H2···H81xi | 3.435 | H83···H82ix | 3.477 |
H5···N1iv | 2.821 | H83···H83ix | 2.648 |
H5···C1iv | 2.929 | H201···N1iv | 2.125 |
H5···H1iv | 2.442 | H201···N2iv | 3.196 |
H6···Cl1viii | 3.379 | H201···C1iv | 3.181 |
H6···C7ii | 3.288 | H201···C3iv | 3.018 |
H6···H11iii | 3.513 | H201···H1iv | 3.328 |
H6···H71ii | 2.674 | H201···H201iv | 2.700 |
H6···H73ii | 3.043 | | |
| | | |
C2—S1—C3 | 88.51 (7) | C2—C1—H1 | 122.0 |
C1—N1—C3 | 109.18 (12) | S1—C2—H2 | 124.6 |
C3—N2—C4 | 123.61 (11) | C1—C2—H2 | 124.6 |
N1—C1—C2 | 116.01 (14) | C4—C5—H5 | 107.7 |
S1—C2—C1 | 110.73 (12) | C6—C5—H5 | 107.7 |
S1—C3—N1 | 115.57 (11) | C9—C5—H5 | 107.7 |
S1—C3—N2 | 123.13 (10) | C5—C6—H6 | 107.9 |
N1—C3—N2 | 121.29 (13) | C7—C6—H6 | 107.9 |
O1—C4—N2 | 121.72 (13) | C8—C6—H6 | 107.9 |
O1—C4—C5 | 122.44 (13) | C6—C7—H71 | 109.5 |
N2—C4—C5 | 115.82 (12) | C6—C7—H72 | 109.5 |
C4—C5—C6 | 108.75 (13) | C6—C7—H73 | 109.5 |
C4—C5—C9 | 110.38 (13) | H71—C7—H72 | 109.5 |
C6—C5—C9 | 114.33 (12) | H71—C7—H73 | 109.5 |
C5—C6—C7 | 111.47 (14) | H72—C7—H73 | 109.5 |
C5—C6—C8 | 111.27 (15) | C6—C8—H81 | 109.5 |
C7—C6—C8 | 110.13 (16) | C6—C8—H82 | 109.5 |
C5—C9—C10 | 120.90 (13) | C6—C8—H83 | 109.5 |
C5—C9—C14 | 121.55 (14) | H81—C8—H82 | 109.5 |
C10—C9—C14 | 117.55 (15) | H81—C8—H83 | 109.5 |
C9—C10—C11 | 121.81 (15) | H82—C8—H83 | 109.5 |
C10—C11—C12 | 119.26 (18) | C9—C10—H10 | 119.1 |
Cl1—C12—C11 | 119.81 (16) | C11—C10—H10 | 119.1 |
Cl1—C12—C13 | 119.81 (15) | C10—C11—H11 | 120.4 |
C11—C12—C13 | 120.38 (18) | C12—C11—H11 | 120.4 |
C12—C13—C14 | 119.87 (16) | C12—C13—H13 | 120.1 |
C9—C14—C13 | 121.11 (16) | C14—C13—H13 | 120.1 |
C3—N2—H201 | 118.2 | C9—C14—H14 | 119.4 |
C4—N2—H201 | 118.2 | C13—C14—H14 | 119.4 |
N1—C1—H1 | 122.0 | | |
| | | |
C2—S1—C3—N1 | −0.12 (15) | C4—C5—C9—C10 | 111.76 (16) |
C2—S1—C3—N2 | 179.25 (16) | C4—C5—C9—C14 | −68.03 (18) |
C3—S1—C2—C1 | 0.05 (14) | C6—C5—C9—C10 | −125.27 (16) |
C1—N1—C3—S1 | 0.2 (2) | C6—C5—C9—C14 | 54.95 (19) |
C1—N1—C3—N2 | −179.23 (16) | C9—C5—C6—C7 | 179.44 (13) |
C3—N1—C1—C2 | −0.1 (2) | C9—C5—C6—C8 | 56.07 (18) |
C3—N2—C4—O1 | 1.9 (2) | C5—C9—C10—C11 | 179.77 (16) |
C3—N2—C4—C5 | −176.51 (15) | C5—C9—C14—C13 | 179.27 (15) |
C4—N2—C3—S1 | 1.5 (2) | C10—C9—C14—C13 | −0.5 (2) |
C4—N2—C3—N1 | −179.13 (16) | C14—C9—C10—C11 | −0.4 (2) |
N1—C1—C2—S1 | 0.0 (2) | C9—C10—C11—C12 | 1.1 (2) |
O1—C4—C5—C6 | −65.6 (2) | C10—C11—C12—Cl1 | 179.43 (14) |
O1—C4—C5—C9 | 60.6 (2) | C10—C11—C12—C13 | −0.9 (2) |
N2—C4—C5—C6 | 112.83 (15) | Cl1—C12—C13—C14 | 179.64 (14) |
N2—C4—C5—C9 | −120.99 (15) | C11—C12—C13—C14 | −0.0 (2) |
C4—C5—C6—C7 | −56.71 (17) | C12—C13—C14—C9 | 0.8 (2) |
C4—C5—C6—C8 | 179.93 (13) | | |
Symmetry codes: (i) −x+1, y, −z−1/2; (ii) −x+1/2, −y+1/2, −z; (iii) x, −y, z−1/2; (iv) −x+1, y, −z+1/2; (v) −x+1/2, y+1/2, −z+1/2; (vi) x, −y, z+1/2; (vii) −x+1/2, y−1/2, −z+1/2; (viii) −x, −y, −z; (ix) −x, y, −z+1/2; (x) −x+1, −y, −z; (xi) x+1/2, −y+1/2, z−1/2; (xii) x−1/2, −y+1/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H201···N1iv | 0.86 | 2.13 | 2.9788 (16) | 172 |
Symmetry code: (iv) −x+1, y, −z+1/2. |
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