5-Acetyl-4-methyl-2-phenyl­amino-1,3-thia­zole

The asymmetric unit of the title compound, C₁₂H₁₂N₂OS, contains two crystallographically independent mol­ecules. Both mol­ecules are essentially planar and stabilized by intra- and inter­molecular hydrogen-bonding inter­actions to form one-dimensional zigzag polymeric chains parallel to the c axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.055
• wR factor = 0.125
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N3     -   C18     ..       5.34 su
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S2     in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

5-Acetyl-4-methyl-2-phenylamino-1,3-thiazole

Crystal data

C12H12N2OS	F(000) = 976
Mr = 232.30	Dx = 1.328 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1480 reflections
a = 12.932 (6) Å	θ = 1.6–26.0°
b = 7.532 (3) Å	µ = 0.26 mm^−1
c = 24.322 (11) Å	T = 293 K
β = 101.236 (9)°	Block, colourless
V = 2323.6 (18) Å^3	0.31 × 0.19 × 0.12 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer	4065 independent reflections
Radiation source: fine-focus sealed tube	2637 reflections with I > 2σI
Graphite monochromator	Rint = 0.049
Detector resolution: 83.66 pixels mm^-1	θmax = 25.0°, θmin = 1.6°
ω scans	h = −15→14
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −7→8
Tmin = 0.924, Tmax = 0.969	l = −28→28
11081 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0551P)^2 + 0.1476P] where P = (Fo^2 + 2Fc^2)/3
4065 reflections	(Δ/σ)max < 0.001
293 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.11715 (6)	0.17457 (11)	0.36646 (3)	0.0531 (3)
S2	0.95293 (6)	0.20100 (12)	0.10301 (3)	0.0540 (3)
O1	0.05122 (18)	0.2456 (3)	0.47004 (9)	0.0735 (7)
O2	1.01763 (18)	0.0760 (4)	0.21506 (9)	0.0862 (8)
N1	0.21706 (18)	0.1096 (3)	0.28282 (10)	0.0555 (7)
H1	0.1532	0.0887	0.2663	0.067*
N2	0.31592 (18)	0.2238 (3)	0.36848 (10)	0.0531 (7)
N3	0.85371 (19)	0.3241 (3)	0.00316 (10)	0.0534 (7)
H3	0.9157	0.3114	−0.0041	0.064*
N4	0.75385 (17)	0.2705 (3)	0.07319 (10)	0.0481 (6)
C1	0.3986 (2)	0.1147 (5)	0.26695 (13)	0.0607 (9)
H1A	0.4229	0.1691	0.3014	0.073*
C2	0.4678 (3)	0.0719 (5)	0.23233 (14)	0.0711 (10)
H2	0.5389	0.0998	0.2436	0.085*
C3	0.4344 (3)	−0.0101 (5)	0.18215 (14)	0.0684 (10)
H3A	0.4824	−0.0400	0.1597	0.082*
C4	0.3300 (3)	−0.0480 (4)	0.16500 (13)	0.0630 (9)
H4	0.3065	−0.1035	0.1307	0.076*
C5	0.2594 (2)	−0.0045 (4)	0.19827 (12)	0.0561 (8)
H5	0.1881	−0.0291	0.1861	0.067*
C6	0.2939 (2)	0.0760 (4)	0.24995 (12)	0.0494 (8)
C7	0.2279 (2)	0.1693 (4)	0.33612 (12)	0.0480 (7)
C8	0.1957 (2)	0.2590 (4)	0.42724 (11)	0.0483 (8)
C9	0.2972 (2)	0.2758 (4)	0.41969 (12)	0.0492 (8)
C10	0.3908 (2)	0.3428 (5)	0.46103 (13)	0.0698 (10)
H10A	0.3816	0.4667	0.4680	0.105*
H10B	0.4535	0.3267	0.4460	0.105*
H10C	0.3971	0.2778	0.4955	0.105*
C11	0.1428 (3)	0.2913 (4)	0.47394 (12)	0.0542 (8)
C12	0.2000 (3)	0.3820 (4)	0.52584 (13)	0.0695 (10)
H12A	0.1506	0.4156	0.5487	0.104*
H12B	0.2348	0.4861	0.5156	0.104*
H12C	0.2514	0.3025	0.5464	0.104*
C13	0.6717 (3)	0.4057 (4)	−0.03923 (14)	0.0654 (9)
H13	0.6463	0.3627	−0.0086	0.078*
C14	0.6035 (3)	0.4808 (5)	−0.08435 (15)	0.0791 (11)
H14	0.5318	0.4861	−0.0839	0.095*
C15	0.6392 (4)	0.5469 (5)	−0.12930 (15)	0.0803 (11)
H15	0.5927	0.5988	−0.1589	0.096*
C16	0.7434 (4)	0.5360 (5)	−0.13022 (14)	0.0762 (11)
H16	0.7681	0.5811	−0.1608	0.091*
C17	0.8135 (3)	0.4597 (4)	−0.08684 (13)	0.0662 (9)
H17	0.8845	0.4511	−0.0886	0.079*
C18	0.7779 (2)	0.3958 (4)	−0.04052 (12)	0.0527 (8)
C19	0.8431 (2)	0.2716 (4)	0.05547 (12)	0.0458 (7)
C20	0.8721 (2)	0.1687 (4)	0.15179 (12)	0.0479 (7)
C21	0.7701 (2)	0.2126 (4)	0.12766 (12)	0.0468 (7)
C22	0.6740 (2)	0.2028 (5)	0.15336 (13)	0.0640 (9)
H22A	0.6567	0.0807	0.1584	0.096*
H22B	0.6161	0.2600	0.1291	0.096*
H22C	0.6877	0.2616	0.1891	0.096*
C23	0.9225 (3)	0.1029 (5)	0.20590 (13)	0.0592 (9)
C24	0.8614 (3)	0.0670 (5)	0.25108 (13)	0.0772 (11)
H24A	0.9062	0.0092	0.2820	0.116*
H24B	0.8025	−0.0083	0.2367	0.116*
H24C	0.8364	0.1771	0.2635	0.116*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0496 (5)	0.0584 (6)	0.0515 (5)	−0.0039 (4)	0.0107 (4)	−0.0011 (4)
S2	0.0448 (4)	0.0652 (6)	0.0529 (5)	−0.0033 (4)	0.0118 (4)	−0.0034 (4)
O1	0.0670 (15)	0.0872 (19)	0.0728 (16)	−0.0034 (14)	0.0296 (12)	0.0009 (13)
O2	0.0561 (14)	0.138 (3)	0.0579 (15)	0.0056 (16)	−0.0063 (12)	−0.0029 (14)
N1	0.0494 (15)	0.0694 (19)	0.0459 (15)	−0.0054 (13)	0.0046 (12)	−0.0102 (13)
N2	0.0526 (15)	0.0603 (18)	0.0450 (15)	−0.0062 (13)	0.0063 (13)	−0.0029 (13)
N3	0.0544 (15)	0.0562 (17)	0.0531 (16)	−0.0069 (14)	0.0188 (13)	0.0007 (13)
N4	0.0469 (14)	0.0500 (16)	0.0489 (15)	−0.0018 (12)	0.0132 (12)	0.0004 (12)
C1	0.058 (2)	0.079 (3)	0.0447 (19)	−0.0096 (19)	0.0086 (16)	−0.0015 (17)
C2	0.061 (2)	0.096 (3)	0.060 (2)	−0.012 (2)	0.0201 (18)	0.004 (2)
C3	0.071 (2)	0.077 (3)	0.063 (2)	0.002 (2)	0.0271 (19)	0.003 (2)
C4	0.083 (3)	0.061 (2)	0.0474 (19)	0.002 (2)	0.0181 (19)	−0.0032 (16)
C5	0.061 (2)	0.054 (2)	0.0512 (19)	−0.0086 (17)	0.0068 (16)	−0.0033 (16)
C6	0.0556 (19)	0.048 (2)	0.0453 (18)	0.0004 (16)	0.0113 (15)	0.0067 (15)
C7	0.0499 (18)	0.0462 (19)	0.0462 (18)	0.0004 (16)	0.0052 (15)	0.0018 (15)
C8	0.0547 (19)	0.0437 (19)	0.0454 (18)	0.0001 (15)	0.0072 (15)	0.0036 (14)
C9	0.0538 (19)	0.050 (2)	0.0435 (18)	−0.0017 (16)	0.0074 (15)	0.0004 (15)
C10	0.062 (2)	0.088 (3)	0.058 (2)	−0.008 (2)	0.0063 (17)	−0.0103 (19)
C11	0.068 (2)	0.044 (2)	0.053 (2)	0.0073 (18)	0.0171 (17)	0.0084 (15)
C12	0.095 (3)	0.064 (2)	0.053 (2)	−0.003 (2)	0.0237 (19)	−0.0021 (17)
C13	0.062 (2)	0.069 (3)	0.060 (2)	−0.0035 (19)	−0.0007 (18)	0.0108 (18)
C14	0.077 (2)	0.082 (3)	0.072 (3)	−0.001 (2)	0.000 (2)	0.009 (2)
C15	0.103 (3)	0.068 (3)	0.060 (2)	0.006 (2)	−0.009 (2)	−0.001 (2)
C16	0.124 (3)	0.061 (2)	0.047 (2)	0.004 (3)	0.024 (2)	0.0021 (18)
C17	0.087 (2)	0.059 (2)	0.056 (2)	−0.002 (2)	0.021 (2)	−0.0004 (18)
C18	0.062 (2)	0.045 (2)	0.0470 (19)	−0.0044 (17)	0.0026 (16)	−0.0012 (15)
C19	0.0477 (18)	0.0424 (19)	0.0491 (19)	−0.0057 (14)	0.0138 (15)	−0.0062 (14)
C20	0.0488 (18)	0.051 (2)	0.0441 (17)	−0.0032 (16)	0.0096 (14)	−0.0079 (15)
C21	0.0508 (18)	0.0417 (19)	0.0509 (19)	−0.0063 (15)	0.0171 (15)	−0.0052 (15)
C22	0.0556 (19)	0.075 (3)	0.066 (2)	−0.0006 (18)	0.0238 (16)	−0.0012 (19)
C23	0.061 (2)	0.064 (2)	0.051 (2)	−0.0051 (19)	0.0074 (17)	−0.0090 (16)
C24	0.089 (3)	0.094 (3)	0.051 (2)	0.001 (2)	0.0190 (19)	0.0063 (19)

Geometric parameters (Å, º)

S1—C7	1.734 (3)	C9—C10	1.502 (4)
S1—C8	1.742 (3)	C10—H10A	0.9600
S2—C19	1.731 (3)	C10—H10B	0.9600
S2—C20	1.744 (3)	C10—H10C	0.9600
O1—C11	1.219 (3)	C11—C12	1.498 (4)
O2—C23	1.223 (3)	C12—H12A	0.9600
N1—C7	1.354 (4)	C12—H12B	0.9600
N1—C6	1.414 (4)	C12—H12C	0.9600
N1—H1	0.8600	C13—C18	1.382 (4)
N2—C7	1.317 (3)	C13—C14	1.387 (4)
N2—C9	1.371 (3)	C13—H13	0.9300
N3—C19	1.364 (3)	C14—C15	1.361 (5)
N3—C18	1.406 (4)	C14—H14	0.9300
N3—H3	0.8600	C15—C16	1.355 (5)
N4—C19	1.309 (3)	C15—H15	0.9300
N4—C21	1.372 (3)	C16—C17	1.375 (5)
C1—C6	1.368 (4)	C16—H16	0.9300
C1—C2	1.381 (4)	C17—C18	1.384 (4)
C1—H1A	0.9300	C17—H17	0.9300
C2—C3	1.361 (4)	C20—C21	1.376 (4)
C2—H2	0.9300	C20—C23	1.438 (4)
C3—C4	1.364 (4)	C21—C22	1.497 (4)
C3—H3A	0.9300	C22—H22A	0.9600
C4—C5	1.372 (4)	C22—H22B	0.9600
C4—H4	0.9300	C22—H22C	0.9600
C5—C6	1.389 (4)	C23—C24	1.498 (4)
C5—H5	0.9300	C24—H24A	0.9600
C8—C9	1.367 (4)	C24—H24B	0.9600
C8—C11	1.456 (4)	C24—H24C	0.9600
C7—S1—C8	88.65 (14)	C11—C12—H12B	109.5
C19—S2—C20	88.56 (14)	H12A—C12—H12B	109.5
C7—N1—C6	130.4 (2)	C11—C12—H12C	109.5
C7—N1—H1	114.8	H12A—C12—H12C	109.5
C6—N1—H1	114.8	H12B—C12—H12C	109.5
C7—N2—C9	110.3 (2)	C18—C13—C14	119.0 (3)
C19—N3—C18	129.4 (3)	C18—C13—H13	120.5
C19—N3—H3	115.3	C14—C13—H13	120.5
C18—N3—H3	115.3	C15—C14—C13	121.5 (4)
C19—N4—C21	109.9 (2)	C15—C14—H14	119.3
C6—C1—C2	119.1 (3)	C13—C14—H14	119.3
C6—C1—H1A	120.4	C16—C15—C14	119.0 (4)
C2—C1—H1A	120.4	C16—C15—H15	120.5
C3—C2—C1	121.5 (3)	C14—C15—H15	120.5
C3—C2—H2	119.3	C15—C16—C17	121.4 (3)
C1—C2—H2	119.3	C15—C16—H16	119.3
C2—C3—C4	119.5 (3)	C17—C16—H16	119.3
C2—C3—H3A	120.3	C16—C17—C18	119.7 (3)
C4—C3—H3A	120.3	C16—C17—H17	120.1
C3—C4—C5	120.2 (3)	C18—C17—H17	120.1
C3—C4—H4	119.9	C13—C18—C17	119.3 (3)
C5—C4—H4	119.9	C13—C18—N3	123.6 (3)
C4—C5—C6	120.3 (3)	C17—C18—N3	117.1 (3)
C4—C5—H5	119.8	N4—C19—N3	124.3 (3)
C6—C5—H5	119.8	N4—C19—S2	116.1 (2)
C1—C6—C5	119.4 (3)	N3—C19—S2	119.6 (2)
C1—C6—N1	123.7 (3)	C21—C20—C23	134.4 (3)
C5—C6—N1	116.9 (3)	C21—C20—S2	109.2 (2)
N2—C7—N1	126.3 (3)	C23—C20—S2	116.5 (2)
N2—C7—S1	115.3 (2)	N4—C21—C20	116.2 (2)
N1—C7—S1	118.4 (2)	N4—C21—C22	115.8 (3)
C9—C8—C11	134.3 (3)	C20—C21—C22	128.0 (3)
C9—C8—S1	109.6 (2)	C21—C22—H22A	109.5
C11—C8—S1	116.0 (2)	C21—C22—H22B	109.5
C8—C9—N2	116.1 (3)	H22A—C22—H22B	109.5
C8—C9—C10	127.7 (3)	C21—C22—H22C	109.5
N2—C9—C10	116.2 (3)	H22A—C22—H22C	109.5
C9—C10—H10A	109.5	H22B—C22—H22C	109.5
C9—C10—H10B	109.5	O2—C23—C20	119.0 (3)
H10A—C10—H10B	109.5	O2—C23—C24	119.5 (3)
C9—C10—H10C	109.5	C20—C23—C24	121.6 (3)
H10A—C10—H10C	109.5	C23—C24—H24A	109.5
H10B—C10—H10C	109.5	C23—C24—H24B	109.5
O1—C11—C8	119.3 (3)	H24A—C24—H24B	109.5
O1—C11—C12	120.5 (3)	C23—C24—H24C	109.5
C8—C11—C12	120.2 (3)	H24A—C24—H24C	109.5
C11—C12—H12A	109.5	H24B—C24—H24C	109.5
C6—C1—C2—C3	−1.0 (5)	C18—C13—C14—C15	−1.0 (6)
C1—C2—C3—C4	1.3 (5)	C13—C14—C15—C16	1.1 (6)
C2—C3—C4—C5	−0.3 (5)	C14—C15—C16—C17	0.1 (6)
C3—C4—C5—C6	−1.0 (5)	C15—C16—C17—C18	−1.4 (5)
C2—C1—C6—C5	−0.3 (5)	C14—C13—C18—C17	−0.4 (5)
C2—C1—C6—N1	178.2 (3)	C14—C13—C18—N3	179.3 (3)
C4—C5—C6—C1	1.3 (5)	C16—C17—C18—C13	1.6 (5)
C4—C5—C6—N1	−177.3 (3)	C16—C17—C18—N3	−178.2 (3)
C7—N1—C6—C1	−5.6 (5)	C19—N3—C18—C13	−8.2 (5)
C7—N1—C6—C5	172.9 (3)	C19—N3—C18—C17	171.5 (3)
C9—N2—C7—N1	179.7 (3)	C21—N4—C19—N3	−179.4 (3)
C9—N2—C7—S1	−1.0 (3)	C21—N4—C19—S2	0.6 (3)
C6—N1—C7—N2	5.8 (5)	C18—N3—C19—N4	4.3 (5)
C6—N1—C7—S1	−173.5 (2)	C18—N3—C19—S2	−175.7 (2)
C8—S1—C7—N2	0.6 (2)	C20—S2—C19—N4	−0.6 (2)
C8—S1—C7—N1	180.0 (2)	C20—S2—C19—N3	179.3 (2)
C7—S1—C8—C9	0.0 (2)	C19—S2—C20—C21	0.5 (2)
C7—S1—C8—C11	−178.5 (2)	C19—S2—C20—C23	179.7 (3)
C11—C8—C9—N2	177.6 (3)	C19—N4—C21—C20	−0.1 (4)
S1—C8—C9—N2	−0.5 (3)	C19—N4—C21—C22	−179.4 (2)
C11—C8—C9—C10	−1.8 (6)	C23—C20—C21—N4	−179.3 (3)
S1—C8—C9—C10	−179.9 (3)	S2—C20—C21—N4	−0.3 (3)
C7—N2—C9—C8	1.0 (4)	C23—C20—C21—C22	−0.1 (6)
C7—N2—C9—C10	−179.6 (3)	S2—C20—C21—C22	178.9 (3)
C9—C8—C11—O1	−172.2 (3)	C21—C20—C23—O2	180.0 (3)
S1—C8—C11—O1	5.8 (4)	S2—C20—C23—O2	1.1 (4)
C9—C8—C11—C12	8.6 (5)	C21—C20—C23—C24	−0.1 (6)
S1—C8—C11—C12	−173.3 (2)	S2—C20—C23—C24	−179.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N2	0.93	2.37	2.991 (4)	124
C13—H13···N4	0.93	2.30	2.917 (4)	123
N1—H1···O2^i	0.86	1.95	2.788 (4)	166
N3—H3···O1^ii	0.86	2.02	2.872 (4)	171
C5—H5···O2^i	0.93	2.57	3.288 (4)	135

Symmetry codes: (i) x−1, y, z; (ii) x+1, −y+1/2, z−1/2.