N-(4-Methyl-3-phenyl-2,3-dihydro-1,3-thia­zol-2-yl­idene)benzamide

Saeed, A.; Bolte, M.

doi:10.1107/S1600536807017138

N-(4-Methyl-3-phenyl-2,3-dihydro-1,3-thiazol-2-ylidene)benzamide

Geometric parameters of the title compound, C₁₈H₁₆N₂OS, are in the normal ranges. The phenyl ring is twisted by 68.22 (7)° out of the plane of the heterocycle.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017138/sg2152sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017138/sg2152Isup2.hkl Contains datablock I

CCDC reference: 647322

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C)= 0.003 Å
R factor = 0.042
wR factor = 0.114
Data-to-parameter ratio = 15.0

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

N-(4-Methyl-3-phenyl-2,3-dihydro-1,3-thiazol-2-ylidene)benzamide top

Crystal data top

C₁₈H₁₆N₂OS	D_x = 1.272 Mg m⁻³
M_r = 308.39	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, R3	Cell parameters from 9559 reflections
Hall symbol: -R 3	θ = 3.4–25.8°
a = 18.8437 (14) Å	µ = 0.20 mm⁻¹
c = 23.561 (2) Å	T = 173 K
V = 7245.3 (10) Å³	Block, colourless
Z = 18	0.26 × 0.24 × 0.20 mm
F(000) = 2916

Data collection top

Stoe IPDSII two-circle diffractometer	3025 independent reflections
Radiation source: fine-focus sealed tube	2336 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 25.7°, θ_min = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −21→21
T_min = 0.939, T_max = 0.950	k = −22→22
11573 measured reflections	l = −26→28

Refinement top

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0665P)² + 2.2717P] where P = (F_o² + 2F_c²)/3
3025 reflections	(Δ/σ)_max < 0.001
201 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Special details top

Experimental. R_f 0.14 (hexane ether–EtOAc 7:3 v/v); IR (KBr, ν, cm^-1): 2938, 1673 (CO), 1600 (C═C), 1514, 1572 (C═N), 1265, 1152, 1050, 783, 736, 700; ¹H NMR (CDCl₃, δ, p.p.m.): 2.07 (s, 3H, C5—Me), 2.48 (s, 3H, Ar—Me), 6.45 (s, 1H, C4—H), 7.14 (2H, AABB), 7.24 (2H, AABB), 7.35 (2H, AABB), 7.67 (2H,AABB); ¹³C NMR (CDCl₃, δ, p.p.m.): 15.1, 21.3, 105.2, 123.7, 128.1, 129.2, 130.0, 132.7.0, 133.8, 134.0, 137.5, 170.1, 179.0; EIMS: m/z 295 (7.0) (M⁺), 215 (36.0), 119 (100), 91 (51), 65 (22).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.15714 (3)	0.08813 (3)	0.42426 (3)	0.05856 (19)
O1	0.19191 (8)	0.23963 (9)	0.40863 (8)	0.0689 (5)
N1	0.29852 (9)	0.10065 (8)	0.42549 (6)	0.0435 (4)
N2	0.30922 (9)	0.22995 (9)	0.41791 (7)	0.0432 (4)
C1	0.26355 (11)	0.14910 (11)	0.42201 (8)	0.0440 (4)
C2	0.24185 (13)	0.01593 (11)	0.42972 (8)	0.0501 (5)
C3	0.16452 (13)	0.00044 (12)	0.43055 (10)	0.0581 (5)
H3	0.1184	−0.0530	0.4342	0.070*
C4	0.26753 (11)	0.27164 (11)	0.41219 (9)	0.0465 (4)
C11	0.38605 (11)	0.13371 (10)	0.42178 (7)	0.0399 (4)
C12	0.41806 (12)	0.11622 (12)	0.37424 (8)	0.0487 (5)
H12	0.3828	0.0842	0.3443	0.058*
C13	0.50140 (14)	0.14549 (13)	0.37059 (10)	0.0573 (5)
H13	0.5234	0.1334	0.3382	0.069*
C14	0.55277 (13)	0.19233 (13)	0.41406 (10)	0.0595 (6)
H14	0.6100	0.2123	0.4116	0.071*
C15	0.52036 (13)	0.21004 (13)	0.46122 (10)	0.0582 (5)
H15	0.5558	0.2428	0.4909	0.070*
C16	0.43667 (12)	0.18048 (11)	0.46561 (8)	0.0491 (5)
H16	0.4146	0.1922	0.4982	0.059*
C21	0.27075 (15)	−0.04472 (12)	0.43248 (10)	0.0606 (6)
H21A	0.2241	−0.0993	0.4403	0.091*
H21B	0.3115	−0.0292	0.4628	0.091*
H21C	0.2956	−0.0455	0.3961	0.091*
C41	0.32054 (10)	0.36292 (11)	0.40957 (8)	0.0402 (4)
C42	0.28854 (11)	0.40924 (12)	0.38642 (8)	0.0461 (4)
H42	0.2340	0.3826	0.3723	0.055*
C43	0.33585 (12)	0.49384 (12)	0.38386 (9)	0.0510 (5)
H43	0.3137	0.5244	0.3671	0.061*
C44	0.41525 (12)	0.53490 (11)	0.40542 (9)	0.0503 (5)
C45	0.44725 (11)	0.48855 (11)	0.42806 (8)	0.0464 (4)
H45	0.5016	0.5155	0.4425	0.056*
C46	0.40106 (10)	0.40360 (11)	0.42986 (8)	0.0413 (4)
H46	0.4243	0.3730	0.4449	0.050*
C47	0.46466 (16)	0.62749 (13)	0.40436 (13)	0.0763 (7)
H47A	0.5007	0.6455	0.3711	0.115*
H47B	0.4978	0.6473	0.4389	0.115*
H47C	0.4275	0.6496	0.4024	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0391 (3)	0.0415 (3)	0.0812 (4)	0.0097 (2)	0.0095 (2)	−0.0056 (2)
O1	0.0297 (7)	0.0479 (8)	0.1235 (14)	0.0153 (6)	0.0054 (7)	−0.0027 (8)
N1	0.0451 (8)	0.0319 (7)	0.0477 (9)	0.0148 (7)	0.0027 (6)	−0.0004 (6)
N2	0.0365 (8)	0.0347 (8)	0.0569 (9)	0.0165 (6)	0.0035 (6)	−0.0026 (6)
C1	0.0401 (9)	0.0374 (9)	0.0492 (10)	0.0154 (8)	0.0039 (8)	−0.0037 (7)
C2	0.0589 (12)	0.0304 (9)	0.0467 (10)	0.0117 (8)	0.0025 (9)	0.0008 (7)
C3	0.0548 (12)	0.0339 (10)	0.0649 (14)	0.0067 (9)	0.0080 (10)	−0.0014 (9)
C4	0.0360 (10)	0.0411 (10)	0.0613 (12)	0.0185 (8)	0.0052 (8)	−0.0030 (8)
C11	0.0472 (10)	0.0310 (8)	0.0427 (10)	0.0204 (7)	0.0010 (7)	0.0037 (7)
C12	0.0614 (12)	0.0453 (10)	0.0438 (10)	0.0300 (9)	−0.0002 (9)	−0.0029 (8)
C13	0.0672 (13)	0.0559 (12)	0.0612 (13)	0.0402 (11)	0.0136 (10)	0.0059 (10)
C14	0.0521 (12)	0.0546 (12)	0.0799 (16)	0.0327 (10)	0.0027 (11)	0.0082 (11)
C15	0.0564 (12)	0.0533 (12)	0.0635 (13)	0.0264 (10)	−0.0130 (10)	−0.0061 (10)
C16	0.0552 (11)	0.0442 (10)	0.0472 (11)	0.0242 (9)	−0.0019 (8)	−0.0047 (8)
C21	0.0809 (15)	0.0348 (10)	0.0597 (13)	0.0242 (10)	−0.0052 (11)	0.0036 (9)
C41	0.0358 (9)	0.0387 (9)	0.0482 (10)	0.0201 (8)	0.0069 (7)	−0.0032 (7)
C42	0.0384 (9)	0.0508 (10)	0.0537 (11)	0.0259 (9)	0.0037 (8)	−0.0024 (8)
C43	0.0530 (11)	0.0484 (11)	0.0623 (13)	0.0333 (10)	0.0076 (9)	0.0047 (9)
C44	0.0497 (11)	0.0395 (10)	0.0625 (12)	0.0227 (9)	0.0090 (9)	0.0016 (8)
C45	0.0387 (9)	0.0409 (10)	0.0559 (11)	0.0172 (8)	0.0023 (8)	−0.0046 (8)
C46	0.0390 (9)	0.0401 (9)	0.0488 (10)	0.0228 (8)	0.0034 (7)	−0.0009 (7)
C47	0.0715 (16)	0.0398 (11)	0.114 (2)	0.0251 (11)	0.0022 (14)	0.0035 (12)

Geometric parameters (Å, º) top

S1—C3	1.732 (2)	C15—C16	1.389 (3)
S1—C1	1.7435 (18)	C15—H15	0.9500
O1—C4	1.242 (2)	C16—H16	0.9500
N1—C1	1.370 (2)	C21—H21A	0.9800
N1—C2	1.412 (2)	C21—H21B	0.9800
N1—C11	1.445 (2)	C21—H21C	0.9800
N2—C1	1.327 (2)	C41—C42	1.396 (3)
N2—C4	1.367 (2)	C41—C46	1.398 (2)
C2—C3	1.336 (3)	C42—C43	1.385 (3)
C2—C21	1.493 (3)	C42—H42	0.9500
C3—H3	0.9500	C43—C44	1.392 (3)
C4—C41	1.497 (2)	C43—H43	0.9500
C11—C16	1.383 (3)	C44—C45	1.392 (3)
C11—C12	1.388 (3)	C44—C47	1.512 (3)
C12—C13	1.383 (3)	C45—C46	1.389 (3)
C12—H12	0.9500	C45—H45	0.9500
C13—C14	1.382 (3)	C46—H46	0.9500
C13—H13	0.9500	C47—H47A	0.9800
C14—C15	1.387 (3)	C47—H47B	0.9800
C14—H14	0.9500	C47—H47C	0.9800

C3—S1—C1	90.97 (9)	C11—C16—H16	120.6
C1—N1—C2	114.45 (15)	C15—C16—H16	120.6
C1—N1—C11	122.33 (14)	C2—C21—H21A	109.5
C2—N1—C11	123.13 (15)	C2—C21—H21B	109.5
C1—N2—C4	115.96 (15)	H21A—C21—H21B	109.5
N2—C1—N1	121.19 (16)	C2—C21—H21C	109.5
N2—C1—S1	129.13 (14)	H21A—C21—H21C	109.5
N1—C1—S1	109.69 (12)	H21B—C21—H21C	109.5
C3—C2—N1	111.95 (17)	C42—C41—C46	118.70 (16)
C3—C2—C21	127.42 (18)	C42—C41—C4	119.06 (16)
N1—C2—C21	120.62 (18)	C46—C41—C4	122.24 (16)
C2—C3—S1	112.92 (14)	C43—C42—C41	120.40 (17)
C2—C3—H3	123.5	C43—C42—H42	119.8
S1—C3—H3	123.5	C41—C42—H42	119.8
O1—C4—N2	125.25 (17)	C42—C43—C44	121.21 (18)
O1—C4—C41	119.97 (16)	C42—C43—H43	119.4
N2—C4—C41	114.78 (15)	C44—C43—H43	119.4
C16—C11—C12	120.73 (18)	C45—C44—C43	118.27 (17)
C16—C11—N1	120.28 (16)	C45—C44—C47	121.35 (19)
C12—C11—N1	118.97 (16)	C43—C44—C47	120.39 (19)
C13—C12—C11	119.81 (19)	C46—C45—C44	121.09 (17)
C13—C12—H12	120.1	C46—C45—H45	119.5
C11—C12—H12	120.1	C44—C45—H45	119.5
C14—C13—C12	120.1 (2)	C45—C46—C41	120.29 (17)
C14—C13—H13	119.9	C45—C46—H46	119.9
C12—C13—H13	119.9	C41—C46—H46	119.9
C13—C14—C15	119.7 (2)	C44—C47—H47A	109.5
C13—C14—H14	120.2	C44—C47—H47B	109.5
C15—C14—H14	120.2	H47A—C47—H47B	109.5
C14—C15—C16	120.8 (2)	C44—C47—H47C	109.5
C14—C15—H15	119.6	H47A—C47—H47C	109.5
C16—C15—H15	119.6	H47B—C47—H47C	109.5
C11—C16—C15	118.88 (19)

C4—N2—C1—N1	177.22 (17)	N1—C11—C12—C13	−178.30 (16)
C4—N2—C1—S1	−3.1 (3)	C11—C12—C13—C14	−0.3 (3)
C2—N1—C1—N2	179.92 (17)	C12—C13—C14—C15	−0.2 (3)
C11—N1—C1—N2	−3.5 (3)	C13—C14—C15—C16	0.7 (3)
C2—N1—C1—S1	0.2 (2)	C12—C11—C16—C15	0.2 (3)
C11—N1—C1—S1	176.78 (13)	N1—C11—C16—C15	178.78 (17)
C3—S1—C1—N2	−179.10 (19)	C14—C15—C16—C11	−0.7 (3)
C3—S1—C1—N1	0.61 (15)	O1—C4—C41—C42	−19.3 (3)
C1—N1—C2—C3	−1.2 (2)	N2—C4—C41—C42	160.02 (17)
C11—N1—C2—C3	−177.76 (17)	O1—C4—C41—C46	160.34 (19)
C1—N1—C2—C21	178.57 (18)	N2—C4—C41—C46	−20.4 (3)
C11—N1—C2—C21	2.0 (3)	C46—C41—C42—C43	−0.2 (3)
N1—C2—C3—S1	1.7 (2)	C4—C41—C42—C43	179.44 (17)
C21—C2—C3—S1	−178.10 (17)	C41—C42—C43—C44	−1.6 (3)
C1—S1—C3—C2	−1.33 (18)	C42—C43—C44—C45	2.1 (3)
C1—N2—C4—O1	−2.7 (3)	C42—C43—C44—C47	−177.5 (2)
C1—N2—C4—C41	178.09 (16)	C43—C44—C45—C46	−0.8 (3)
C1—N1—C11—C16	70.7 (2)	C47—C44—C45—C46	178.8 (2)
C2—N1—C11—C16	−113.0 (2)	C44—C45—C46—C41	−1.0 (3)
C1—N1—C11—C12	−110.8 (2)	C42—C41—C46—C45	1.5 (3)
C2—N1—C11—C12	65.5 (2)	C4—C41—C46—C45	−178.15 (17)
C16—C11—C12—C13	0.3 (3)

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N-(4-Methyl-3-phenyl-2,3-dihydro-1,3-thia­zol-2-yl­idene)benzamide

Supporting information

Key indicators

checkCIF/PLATON results

N-(4-Methyl-3-phenyl-2,3-dihydro-1,3-thiazol-2-ylidene)benzamide