5-Acetyl-4-methyl-2-(o-toluidinyl)-1,3-thia­zole

In the title compound, C₁₃H₁₄N₂OS, the benzene and thia­zole rings make a dihedral angle of 73.44 (10)°. The intermolecular N—H...N hydrogen bonds link the mol­ecules into centrosymmetric dimers. The crystal packing is further stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.044
• wR factor = 0.122
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

5-acetyl-4-methyl-2-(o-toluidinyl)-1,3-thiazole

Crystal data

C13H14N2OS	F(000) = 520
Mr = 246.32	Dx = 1.299 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 871 reflections
a = 10.797 (2) Å	θ = 2.2–26.5°
b = 11.571 (2) Å	µ = 0.24 mm^−1
c = 12.0982 (16) Å	T = 273 K
β = 123.576 (11)°	Block, colourless
V = 1259.3 (4) Å^3	0.41 × 0.40 × 0.33 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2610 independent reflections
Radiation source: fine-focus sealed tube	2343 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 83.66 pixels mm^-1	θmax = 26.5°, θmin = 2.2°
ω scans	h = −13→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
Tmin = 0.907, Tmax = 0.924	l = −14→15
6884 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0659P)^2 + 0.3401P] where P = (Fo^2 + 2Fc^2)/3
2610 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.36514 (5)	0.14029 (4)	0.09201 (4)	0.04631 (17)
O1	0.56321 (19)	0.21909 (18)	0.47003 (16)	0.0833 (6)
N1	0.11037 (16)	0.02748 (15)	−0.07959 (14)	0.0471 (4)
H1A	0.0377	−0.0165	−0.0963	0.057*
N2	0.18362 (15)	0.04675 (12)	0.14127 (14)	0.0400 (3)
C1	0.0342 (2)	0.14303 (15)	−0.27556 (18)	0.0450 (4)
C2	0.0492 (3)	0.1663 (2)	−0.3802 (2)	0.0599 (5)
H2B	−0.0124	0.2212	−0.4431	0.072*
C3	0.1522 (3)	0.1106 (2)	−0.3932 (2)	0.0691 (6)
H3A	0.1592	0.1275	−0.4647	0.083*
C4	0.2453 (3)	0.0300 (2)	−0.3014 (3)	0.0683 (6)
H4A	0.3172	−0.0061	−0.3090	0.082*
C5	0.2314 (2)	0.00262 (18)	−0.1972 (2)	0.0548 (5)
H5A	0.2928	−0.0530	−0.1353	0.066*
C6	0.12603 (19)	0.05827 (15)	−0.18549 (16)	0.0415 (4)
C7	−0.0755 (3)	0.2078 (2)	−0.2597 (2)	0.0646 (6)
H7A	−0.1535	0.1564	−0.2754	0.097*
H7B	−0.1171	0.2703	−0.3223	0.097*
H7C	−0.0260	0.2381	−0.1712	0.097*
C8	0.20538 (17)	0.06492 (14)	0.04581 (16)	0.0385 (4)
C9	0.4052 (2)	0.14896 (15)	0.25331 (18)	0.0444 (4)
C10	0.29605 (19)	0.09372 (15)	0.25821 (17)	0.0417 (4)
C11	0.5305 (2)	0.21665 (18)	0.3561 (2)	0.0554 (5)
C12	0.6173 (3)	0.2869 (2)	0.3164 (3)	0.0784 (7)
H12A	0.7008	0.3222	0.3937	0.118*
H12B	0.5544	0.3459	0.2549	0.118*
H12C	0.6520	0.2375	0.2753	0.118*
C13	0.2875 (2)	0.0832 (2)	0.37681 (19)	0.0589 (5)
H13A	0.1870	0.0666	0.3486	0.088*
H13B	0.3187	0.1545	0.4255	0.088*
H13C	0.3514	0.0218	0.4326	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0391 (3)	0.0552 (3)	0.0480 (3)	−0.00770 (18)	0.0262 (2)	0.00222 (19)
O1	0.0629 (10)	0.1168 (15)	0.0560 (10)	−0.0252 (10)	0.0240 (8)	−0.0206 (9)
N1	0.0389 (7)	0.0656 (10)	0.0388 (8)	−0.0114 (7)	0.0227 (7)	−0.0005 (7)
N2	0.0366 (7)	0.0460 (8)	0.0405 (7)	−0.0021 (6)	0.0233 (6)	0.0006 (6)
C1	0.0450 (9)	0.0461 (9)	0.0432 (9)	−0.0075 (8)	0.0239 (8)	−0.0054 (7)
C2	0.0674 (13)	0.0632 (12)	0.0469 (11)	−0.0074 (11)	0.0302 (10)	0.0066 (9)
C3	0.0853 (16)	0.0842 (16)	0.0587 (13)	−0.0201 (14)	0.0530 (13)	−0.0069 (12)
C4	0.0736 (14)	0.0789 (15)	0.0838 (16)	−0.0071 (12)	0.0633 (14)	−0.0124 (13)
C5	0.0518 (11)	0.0582 (11)	0.0638 (12)	0.0012 (9)	0.0379 (10)	0.0021 (9)
C6	0.0407 (9)	0.0484 (9)	0.0399 (9)	−0.0093 (7)	0.0250 (8)	−0.0045 (7)
C7	0.0597 (12)	0.0661 (13)	0.0663 (13)	0.0122 (11)	0.0337 (11)	0.0028 (11)
C8	0.0335 (8)	0.0419 (9)	0.0430 (9)	0.0003 (7)	0.0229 (7)	0.0043 (7)
C9	0.0392 (9)	0.0467 (10)	0.0455 (9)	−0.0013 (7)	0.0222 (8)	−0.0001 (7)
C10	0.0403 (9)	0.0421 (9)	0.0432 (9)	0.0020 (7)	0.0235 (8)	0.0010 (7)
C11	0.0432 (10)	0.0576 (12)	0.0575 (12)	−0.0057 (9)	0.0229 (9)	−0.0081 (9)
C12	0.0642 (14)	0.0787 (16)	0.0871 (17)	−0.0309 (12)	0.0385 (13)	−0.0175 (13)
C13	0.0619 (12)	0.0750 (14)	0.0470 (10)	−0.0110 (11)	0.0347 (10)	−0.0091 (10)

Geometric parameters (Å, º)

S1—C8	1.7269 (16)	C4—H4A	0.9300
S1—C9	1.7527 (19)	C5—C6	1.381 (3)
O1—C11	1.219 (3)	C5—H5A	0.9300
N1—C8	1.349 (2)	C7—H7A	0.9600
N1—C6	1.427 (2)	C7—H7B	0.9600
N1—H1A	0.8600	C7—H7C	0.9600
N2—C8	1.317 (2)	C9—C10	1.370 (2)
N2—C10	1.368 (2)	C9—C11	1.459 (3)
C1—C2	1.389 (3)	C10—C13	1.493 (2)
C1—C6	1.392 (3)	C11—C12	1.506 (3)
C1—C7	1.500 (3)	C12—H12A	0.9600
C2—C3	1.367 (3)	C12—H12B	0.9600
C2—H2B	0.9300	C12—H12C	0.9600
C3—C4	1.370 (4)	C13—H13A	0.9600
C3—H3A	0.9300	C13—H13B	0.9600
C4—C5	1.387 (3)	C13—H13C	0.9600
C8—S1—C9	88.65 (8)	H7A—C7—H7C	109.5
C8—N1—C6	122.38 (14)	H7B—C7—H7C	109.5
C8—N1—H1A	118.8	N2—C8—N1	122.80 (15)
C6—N1—H1A	118.8	N2—C8—S1	115.32 (13)
C8—N2—C10	110.92 (14)	N1—C8—S1	121.89 (13)
C2—C1—C6	117.26 (18)	C10—C9—C11	128.87 (18)
C2—C1—C7	121.21 (19)	C10—C9—S1	109.45 (13)
C6—C1—C7	121.53 (17)	C11—C9—S1	121.41 (14)
C3—C2—C1	121.7 (2)	N2—C10—C9	115.67 (16)
C3—C2—H2B	119.1	N2—C10—C13	118.07 (16)
C1—C2—H2B	119.1	C9—C10—C13	126.24 (17)
C2—C3—C4	120.42 (19)	O1—C11—C9	121.89 (19)
C2—C3—H3A	119.8	O1—C11—C12	120.4 (2)
C4—C3—H3A	119.8	C9—C11—C12	117.72 (19)
C3—C4—C5	119.5 (2)	C11—C12—H12A	109.5
C3—C4—H4A	120.3	C11—C12—H12B	109.5
C5—C4—H4A	120.3	H12A—C12—H12B	109.5
C6—C5—C4	119.8 (2)	C11—C12—H12C	109.5
C6—C5—H5A	120.1	H12A—C12—H12C	109.5
C4—C5—H5A	120.1	H12B—C12—H12C	109.5
C5—C6—C1	121.29 (17)	C10—C13—H13A	109.5
C5—C6—N1	119.26 (17)	C10—C13—H13B	109.5
C1—C6—N1	119.45 (16)	H13A—C13—H13B	109.5
C1—C7—H7A	109.5	C10—C13—H13C	109.5
C1—C7—H7B	109.5	H13A—C13—H13C	109.5
H7A—C7—H7B	109.5	H13B—C13—H13C	109.5
C1—C7—H7C	109.5
C6—C1—C2—C3	−1.6 (3)	C6—N1—C8—S1	−7.2 (2)
C7—C1—C2—C3	177.8 (2)	C9—S1—C8—N2	−0.46 (14)
C1—C2—C3—C4	−0.5 (4)	C9—S1—C8—N1	179.65 (16)
C2—C3—C4—C5	1.9 (4)	C8—S1—C9—C10	0.56 (14)
C3—C4—C5—C6	−1.2 (3)	C8—S1—C9—C11	−173.98 (16)
C4—C5—C6—C1	−0.9 (3)	C8—N2—C10—C9	0.3 (2)
C4—C5—C6—N1	178.55 (18)	C8—N2—C10—C13	178.77 (16)
C2—C1—C6—C5	2.3 (3)	C11—C9—C10—N2	173.43 (18)
C7—C1—C6—C5	−177.03 (18)	S1—C9—C10—N2	−0.6 (2)
C2—C1—C6—N1	−177.21 (17)	C11—C9—C10—C13	−4.9 (3)
C7—C1—C6—N1	3.5 (3)	S1—C9—C10—C13	−178.96 (16)
C8—N1—C6—C5	77.9 (2)	C10—C9—C11—O1	9.9 (3)
C8—N1—C6—C1	−102.6 (2)	S1—C9—C11—O1	−176.69 (18)
C10—N2—C8—N1	−179.90 (16)	C10—C9—C11—C12	−168.5 (2)
C10—N2—C8—S1	0.21 (19)	S1—C9—C11—C12	4.9 (3)
C6—N1—C8—N2	172.96 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O1	0.96	2.50	2.982 (4)	111
N1—H1A···N2^i	0.86	2.17	2.958 (3)	153

Symmetry code: (i) −x, −y, −z.