N-Benzoyl-N′-(2-methyl­phen­yl)thio­urea

In the title compound, C₁₅H₁₄N₂OS, inter­molecular N—H...S hydrogen bonds link pairs of mol­ecules. The steric hindrance of the o-methyl group restricts the formation of a mol­ecular conjugated plane and π–π stacking. The presence of a hydrogen-bond acceptor atom is more helpful for the thio­urea ligand to promote its stability.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.109
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

N-Benzoyl-N'-(2-methylphenyl)thiourea

Crystal data

C15H14N2OS	F(000) = 568
Mr = 270.34	Dx = 1.305 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.6441 (10) Å	Cell parameters from 2356 reflections
b = 25.165 (4) Å	θ = 2.7–25.7°
c = 9.6851 (17) Å	µ = 0.23 mm^−1
β = 90.216 (3)°	T = 294 K
V = 1375.6 (4) Å^3	Block, colorless
Z = 4	0.36 × 0.32 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2792 independent reflections
Radiation source: fine-focus sealed tube	1816 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 26.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→6
Tmin = 0.910, Tmax = 0.942	k = −31→31
7656 measured reflections	l = −6→12

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0498P)^2 + 0.1902P] where P = (Fo^2 + 2Fc^2)/3
2792 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

Experimental. The infrared spectrum was recorded in the range of 4000–400?cm-1 on a Nicolet NEXUS 670?F T—IR spectrometer, using KBr pellets. 1H NMR spectrum was obtained on an INOVA-400?MHz superconduction spectrometer, DMSO-d6 was used as the solvent and TMS as internal standard, and the chemical shifts are expressed as delta. Elemental analyses were carried out on a PE-2400 CHN instrument. Melting point determination was performed in an open capillary tube and is uncorrected.

N-Benzoyl-N'-(o-methylphenyl)thiourea Color: colorless, Yield: 87%. Melting Point: 116–118(°C). Elemental analysis (%) found (calcd.): C, 65.45(66.67); H, 4.98(5.19); N, 10.76(10.37). IR (KBr, cm-1): 3268 (N—H), 1670 (C=O), 1586, 1527 (C=C), 1262(C=S), 1154. 1H NMR(delta, p.p.m.): 2.26 (s, 3H, CH3); 7.20–8.00 (m, 9H, C6H5, C6H4); 11.61 (s, 1H, NH); 12.29 (s, 1H, NH).

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.64767 (12)	0.44364 (2)	0.63254 (6)	0.0676 (2)
N1	0.7095 (3)	0.35643 (6)	0.47815 (17)	0.0486 (4)
H1	0.657 (4)	0.3397 (8)	0.406 (2)	0.059 (6)*
N2	0.4401 (3)	0.41790 (6)	0.39893 (16)	0.0483 (4)
H2	0.388 (4)	0.4499 (8)	0.409 (2)	0.053 (6)*
O1	0.4452 (3)	0.34613 (5)	0.25749 (15)	0.0696 (5)
C1	0.6042 (3)	0.40303 (7)	0.49881 (18)	0.0456 (5)
C2	0.8678 (3)	0.32847 (7)	0.56687 (18)	0.0460 (5)
C3	0.8358 (3)	0.27361 (8)	0.57925 (19)	0.0486 (5)
C4	0.9884 (4)	0.24641 (9)	0.6661 (2)	0.0675 (6)
H4	0.9690	0.2100	0.6775	0.081*
C5	1.1671 (5)	0.27173 (12)	0.7357 (2)	0.0791 (8)
H5	1.2652	0.2526	0.7949	0.095*
C6	1.2022 (4)	0.32515 (12)	0.7187 (2)	0.0747 (7)
H6	1.3264	0.3421	0.7643	0.090*
C7	1.0531 (4)	0.35382 (9)	0.6338 (2)	0.0592 (6)
H7	1.0769	0.3901	0.6215	0.071*
C8	0.6458 (4)	0.24438 (8)	0.5012 (2)	0.0626 (6)
H8A	0.6338	0.2087	0.5358	0.094*
H8B	0.6851	0.2435	0.4049	0.094*
H8C	0.4970	0.2623	0.5131	0.094*
C9	0.3601 (4)	0.38939 (7)	0.28725 (19)	0.0488 (5)
C10	0.1637 (3)	0.41274 (7)	0.20478 (19)	0.0468 (5)
C11	0.0082 (4)	0.45052 (7)	0.2554 (2)	0.0543 (5)
H11	0.0268	0.4635	0.3447	0.065*
C12	−0.1745 (4)	0.46888 (9)	0.1731 (2)	0.0645 (6)
H12	−0.2772	0.4947	0.2068	0.077*
C13	−0.2056 (4)	0.44941 (9)	0.0421 (3)	0.0697 (6)
H13	−0.3302	0.4617	−0.0123	0.084*
C14	−0.0532 (4)	0.41187 (9)	−0.0087 (2)	0.0712 (7)
H14	−0.0742	0.3987	−0.0976	0.085*
C15	0.1302 (4)	0.39367 (8)	0.0717 (2)	0.0611 (6)
H15	0.2333	0.3683	0.0366	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.1033 (5)	0.0452 (3)	0.0542 (3)	0.0130 (3)	−0.0247 (3)	−0.0140 (2)
N1	0.0641 (11)	0.0384 (9)	0.0433 (9)	0.0030 (8)	−0.0099 (8)	−0.0053 (7)
N2	0.0682 (11)	0.0317 (8)	0.0448 (9)	0.0049 (8)	−0.0104 (8)	−0.0044 (7)
O1	0.0987 (12)	0.0457 (8)	0.0642 (9)	0.0174 (8)	−0.0295 (8)	−0.0185 (7)
C1	0.0606 (12)	0.0349 (9)	0.0412 (10)	−0.0017 (9)	−0.0029 (9)	0.0008 (8)
C2	0.0492 (11)	0.0489 (11)	0.0398 (10)	0.0061 (9)	−0.0004 (8)	−0.0020 (8)
C3	0.0539 (12)	0.0473 (11)	0.0446 (11)	0.0085 (9)	0.0035 (9)	0.0018 (9)
C4	0.0758 (17)	0.0599 (13)	0.0669 (14)	0.0192 (12)	−0.0004 (12)	0.0096 (11)
C5	0.0760 (18)	0.095 (2)	0.0660 (16)	0.0372 (15)	−0.0138 (13)	0.0017 (14)
C6	0.0570 (15)	0.100 (2)	0.0667 (16)	0.0151 (13)	−0.0145 (12)	−0.0204 (14)
C7	0.0568 (14)	0.0619 (13)	0.0589 (13)	0.0016 (11)	−0.0043 (11)	−0.0087 (10)
C8	0.0707 (15)	0.0443 (11)	0.0727 (14)	−0.0018 (10)	0.0010 (11)	0.0049 (10)
C9	0.0670 (13)	0.0359 (10)	0.0434 (11)	−0.0001 (9)	−0.0053 (9)	−0.0037 (8)
C10	0.0577 (12)	0.0373 (10)	0.0453 (11)	−0.0030 (9)	−0.0052 (9)	0.0008 (8)
C11	0.0571 (13)	0.0509 (12)	0.0550 (12)	−0.0056 (10)	0.0018 (10)	−0.0029 (10)
C12	0.0534 (14)	0.0604 (13)	0.0797 (16)	0.0064 (10)	0.0055 (12)	0.0024 (12)
C13	0.0641 (15)	0.0739 (16)	0.0710 (16)	0.0057 (12)	−0.0147 (12)	0.0123 (13)
C14	0.0866 (18)	0.0725 (15)	0.0543 (13)	0.0087 (13)	−0.0186 (12)	−0.0035 (11)
C15	0.0776 (15)	0.0569 (12)	0.0487 (12)	0.0114 (11)	−0.0119 (11)	−0.0063 (10)

Geometric parameters (Å, º)

S1—C1	1.6671 (18)	C6—H6	0.9300
N1—C1	1.330 (2)	C7—H7	0.9300
N1—C2	1.424 (2)	C8—H8A	0.9600
N1—H1	0.87 (2)	C8—H8B	0.9600
N2—C9	1.373 (2)	C8—H8C	0.9600
N2—C1	1.388 (2)	C9—C10	1.485 (3)
N2—H2	0.86 (2)	C10—C11	1.385 (3)
O1—C9	1.225 (2)	C10—C15	1.388 (3)
C2—C7	1.384 (3)	C11—C12	1.380 (3)
C2—C3	1.397 (3)	C11—H11	0.9300
C3—C4	1.383 (3)	C12—C13	1.371 (3)
C3—C8	1.502 (3)	C12—H12	0.9300
C4—C5	1.369 (3)	C13—C14	1.370 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.369 (4)	C14—C15	1.372 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.378 (3)	C15—H15	0.9300
C1—N1—C2	128.67 (17)	C3—C8—H8A	109.5
C1—N1—H1	113.3 (14)	C3—C8—H8B	109.5
C2—N1—H1	117.4 (13)	H8A—C8—H8B	109.5
C9—N2—C1	128.66 (17)	C3—C8—H8C	109.5
C9—N2—H2	117.9 (13)	H8A—C8—H8C	109.5
C1—N2—H2	113.4 (13)	H8B—C8—H8C	109.5
N1—C1—N2	115.47 (16)	O1—C9—N2	121.47 (18)
N1—C1—S1	126.36 (15)	O1—C9—C10	121.17 (17)
N2—C1—S1	118.16 (14)	N2—C9—C10	117.36 (16)
C7—C2—C3	120.86 (18)	C11—C10—C15	118.79 (19)
C7—C2—N1	121.75 (18)	C11—C10—C9	123.66 (17)
C3—C2—N1	117.33 (17)	C15—C10—C9	117.49 (18)
C4—C3—C2	117.43 (19)	C12—C11—C10	119.9 (2)
C4—C3—C8	120.35 (19)	C12—C11—H11	120.0
C2—C3—C8	122.21 (17)	C10—C11—H11	120.0
C5—C4—C3	121.7 (2)	C13—C12—C11	120.5 (2)
C5—C4—H4	119.2	C13—C12—H12	119.8
C3—C4—H4	119.2	C11—C12—H12	119.8
C4—C5—C6	120.3 (2)	C14—C13—C12	120.0 (2)
C4—C5—H5	119.9	C14—C13—H13	120.0
C6—C5—H5	119.9	C12—C13—H13	120.0
C5—C6—C7	119.8 (2)	C13—C14—C15	120.0 (2)
C5—C6—H6	120.1	C13—C14—H14	120.0
C7—C6—H6	120.1	C15—C14—H14	120.0
C6—C7—C2	119.8 (2)	C14—C15—C10	120.8 (2)
C6—C7—H7	120.1	C14—C15—H15	119.6
C2—C7—H7	120.1	C10—C15—H15	119.6
C2—N1—C1—N2	−173.91 (18)	N1—C2—C7—C6	−179.96 (19)
C2—N1—C1—S1	4.9 (3)	C1—N2—C9—O1	−5.6 (3)
C9—N2—C1—N1	5.0 (3)	C1—N2—C9—C10	173.57 (18)
C9—N2—C1—S1	−173.91 (16)	O1—C9—C10—C11	157.1 (2)
C1—N1—C2—C7	−45.1 (3)	N2—C9—C10—C11	−22.0 (3)
C1—N1—C2—C3	137.7 (2)	O1—C9—C10—C15	−20.1 (3)
C7—C2—C3—C4	3.2 (3)	N2—C9—C10—C15	160.73 (18)
N1—C2—C3—C4	−179.58 (18)	C15—C10—C11—C12	−0.7 (3)
C7—C2—C3—C8	−176.17 (19)	C9—C10—C11—C12	−177.87 (19)
N1—C2—C3—C8	1.0 (3)	C10—C11—C12—C13	1.0 (3)
C2—C3—C4—C5	−1.2 (3)	C11—C12—C13—C14	−0.7 (4)
C8—C3—C4—C5	178.2 (2)	C12—C13—C14—C15	0.1 (4)
C3—C4—C5—C6	−1.3 (4)	C13—C14—C15—C10	0.2 (4)
C4—C5—C6—C7	1.7 (4)	C11—C10—C15—C14	0.1 (3)
C5—C6—C7—C2	0.4 (3)	C9—C10—C15—C14	177.5 (2)
C3—C2—C7—C6	−2.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1^i	0.86 (2)	2.72 (2)	3.5326 (18)	157.9 (17)
N1—H1···O1	0.87 (2)	1.87 (2)	2.614 (2)	142.4 (19)

Symmetry code: (i) −x+1, −y+1, −z+1.