N-(3-Methyl-phen-yl)-N'-(4-nitro-benzo-yl)thio-urea.

Two mol-ecules of the title compound, C(15)H(13)N(3)O(3)S, are linked by an inter-molecular N-H⋯S hydrogen bond. There is also an intra-molecular N-H⋯O hydrogen bond, forming a six-membered ring. The steric restriction of the m-methyl and p-nitro groups, as well as the intra-molecular hydrogen bond, are the main factors influencing the mol-ecular conformation.

Related literature

For general background, see: Su et al. (2006 ▶). For related coordination compounds, see: Su et al. (2005 ▶); Xian et al. (2004 ▶). For related structures, see: Su (2005 ▶, 2007 ▶); Yusof et al. (2007 ▶).

Experimental

Crystal data

C15H13N3O3S

M = 315.34

Monoclinic,

a = 11.381 (10) Å

b = 8.549 (8) Å

c = 15.653 (12) Å

β = 108.012 (16)°

V = 1448 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 296 (2) K

0.30 × 0.29 × 0.26 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.609, T max = 1.000 (expected range = 0.572–0.940)

7125 measured reflections

2692 independent reflections

2072 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.141

S = 0.89

2692 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: APEX2 and SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029425/bv2107sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029425/bv2107Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H13N3O3S	F(000) = 656
Mr = 315.34	Dx = 1.446 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.381 (10) Å	Cell parameters from 2974 reflections
b = 8.549 (8) Å	θ = 2.7–29.0°
c = 15.653 (12) Å	µ = 0.24 mm−1
β = 108.012 (16)°	T = 296 K
V = 1448 (3) Å3	Block, yellow
Z = 4	0.30 × 0.29 × 0.26 mm

Bruker APEXII CCD area-detector diffractometer	2692 independent reflections
Radiation source: fine-focus sealed tube	2072 reflections with I > 2σ(I)
graphite	Rint = 0.059
φ and ω scans	θmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −13→13
Tmin = 0.609, Tmax = 1.000	k = −5→10
7125 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.1P)2 + 0.161P] where P = (Fo2 + 2Fc2)/3
S = 0.89	(Δ/σ)max < 0.001
2692 reflections	Δρmax = 0.29 e Å−3
201 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (4)

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.

	x	y	z	Uiso*/Ueq
S1	0.16111 (5)	0.07187 (6)	0.10213 (3)	0.0457 (2)
C6	−0.05997 (17)	0.3452 (2)	−0.17937 (12)	0.0385 (5)
C8	0.14304 (16)	0.2443 (2)	0.05209 (11)	0.0368 (5)
N2	0.05371 (14)	0.25694 (19)	−0.03121 (10)	0.0395 (4)
H2'	0.0037	0.1792	−0.0469	0.047*
C9	0.30022 (17)	0.3945 (2)	0.16605 (12)	0.0379 (5)
C7	0.03499 (18)	0.3776 (3)	−0.09162 (13)	0.0413 (5)
O3	0.09358 (15)	0.4980 (2)	−0.07658 (10)	0.0612 (5)
N4	0.20710 (15)	0.3727 (2)	0.08184 (10)	0.0416 (4)
H4'	0.1908	0.4522	0.0464	0.050*
C10	0.28304 (18)	0.3445 (3)	0.24483 (12)	0.0427 (5)
H10	0.2111	0.2913	0.2433	0.051*
N1	−0.30000 (18)	0.2241 (2)	−0.43126 (12)	0.0545 (5)
C3	−0.21803 (18)	0.2731 (2)	−0.34317 (12)	0.0406 (5)
C1	−0.16868 (17)	0.2707 (2)	−0.18569 (12)	0.0391 (5)
H1	−0.1879	0.2449	−0.1338	0.047*
C2	−0.24957 (18)	0.2339 (2)	−0.26833 (13)	0.0422 (5)
H2	−0.3239	0.1835	−0.2733	0.051*
C12	0.4762 (2)	0.4543 (3)	0.32628 (15)	0.0544 (6)
H12	0.5374	0.4737	0.3804	0.065*
C11	0.37229 (19)	0.3729 (3)	0.32641 (13)	0.0465 (5)
C5	−0.03345 (18)	0.3910 (3)	−0.25606 (13)	0.0465 (5)
H5	0.0384	0.4468	−0.2515	0.056*
C4	−0.11358 (19)	0.3537 (3)	−0.33902 (13)	0.0470 (5)
H4	−0.0967	0.3830	−0.3912	0.056*
C14	0.40313 (18)	0.4767 (3)	0.16660 (14)	0.0479 (5)
H14	0.4140	0.5118	0.1133	0.058*
C13	0.49105 (19)	0.5068 (3)	0.24843 (16)	0.0539 (6)
H13	0.5613	0.5639	0.2501	0.065*
O1	−0.27911 (18)	0.2717 (3)	−0.49730 (10)	0.0787 (6)
O2	−0.38159 (19)	0.1337 (3)	−0.43392 (12)	0.0918 (7)
C15	0.3541 (3)	0.3154 (4)	0.41178 (14)	0.0725 (8)
H15A	0.3351	0.2057	0.4065	0.109*
H15B	0.2872	0.3715	0.4228	0.109*
H15C	0.4284	0.3321	0.4607	0.109*

	U11	U22	U33	U12	U13	U23
S1	0.0441 (4)	0.0420 (4)	0.0431 (3)	0.0008 (2)	0.0017 (2)	0.0030 (2)
C6	0.0384 (10)	0.0398 (11)	0.0356 (10)	0.0041 (9)	0.0088 (8)	0.0034 (9)
C8	0.0325 (9)	0.0458 (12)	0.0321 (9)	0.0017 (8)	0.0100 (8)	−0.0033 (8)
N2	0.0390 (9)	0.0397 (9)	0.0346 (8)	−0.0011 (7)	0.0039 (7)	0.0009 (7)
C9	0.0325 (9)	0.0403 (11)	0.0369 (10)	0.0032 (8)	0.0050 (8)	−0.0037 (9)
C7	0.0398 (11)	0.0424 (11)	0.0392 (10)	−0.0006 (9)	0.0083 (8)	0.0004 (9)
O3	0.0644 (10)	0.0559 (10)	0.0488 (9)	−0.0186 (9)	−0.0035 (7)	0.0098 (8)
N4	0.0423 (9)	0.0412 (10)	0.0357 (8)	−0.0034 (8)	0.0038 (7)	0.0016 (8)
C10	0.0379 (10)	0.0470 (12)	0.0408 (11)	−0.0010 (9)	0.0086 (8)	−0.0046 (10)
N1	0.0497 (11)	0.0658 (13)	0.0411 (10)	0.0018 (10)	0.0036 (8)	−0.0009 (9)
C3	0.0378 (10)	0.0457 (12)	0.0339 (10)	0.0052 (9)	0.0045 (8)	−0.0005 (9)
C1	0.0433 (11)	0.0407 (11)	0.0342 (9)	0.0019 (9)	0.0134 (8)	0.0035 (9)
C2	0.0349 (10)	0.0448 (11)	0.0458 (11)	0.0011 (9)	0.0108 (8)	0.0029 (9)
C12	0.0398 (12)	0.0633 (15)	0.0474 (12)	0.0050 (11)	−0.0051 (9)	−0.0084 (11)
C11	0.0470 (12)	0.0497 (12)	0.0379 (10)	0.0091 (10)	0.0058 (9)	−0.0015 (10)
C5	0.0362 (10)	0.0610 (14)	0.0415 (11)	−0.0053 (10)	0.0110 (9)	0.0039 (10)
C4	0.0450 (11)	0.0609 (14)	0.0365 (10)	0.0010 (10)	0.0145 (9)	0.0052 (10)
C14	0.0391 (11)	0.0546 (13)	0.0490 (12)	0.0009 (10)	0.0120 (9)	0.0014 (10)
C13	0.0313 (10)	0.0620 (15)	0.0617 (13)	−0.0068 (10)	0.0046 (9)	−0.0052 (12)
O1	0.0929 (14)	0.0997 (16)	0.0343 (8)	−0.0134 (12)	0.0062 (8)	0.0072 (9)
O2	0.0754 (12)	0.1309 (19)	0.0583 (11)	−0.0485 (14)	0.0046 (9)	−0.0138 (12)
C15	0.0825 (18)	0.090 (2)	0.0401 (12)	−0.0026 (16)	0.0122 (12)	0.0013 (13)

S1—C8	1.652 (3)	C3—C4	1.358 (3)
C6—C1	1.368 (3)	C3—C2	1.369 (3)
C6—C5	1.382 (3)	C1—C2	1.372 (3)
C6—C7	1.488 (3)	C1—H1	0.9300
C8—N4	1.320 (3)	C2—H2	0.9300
C8—N2	1.388 (2)	C12—C13	1.358 (4)
N2—C7	1.371 (3)	C12—C11	1.372 (3)
N2—H2'	0.8600	C12—H12	0.9300
C9—C14	1.364 (3)	C11—C15	1.497 (3)
C9—C10	1.375 (3)	C5—C4	1.374 (3)
C9—N4	1.425 (3)	C5—H5	0.9300
C7—O3	1.210 (3)	C4—H4	0.9300
N4—H4'	0.8600	C14—C13	1.384 (3)
C10—C11	1.385 (3)	C14—H14	0.9300
C10—H10	0.9300	C13—H13	0.9300
N1—O2	1.199 (3)	C15—H15A	0.9600
N1—O1	1.201 (3)	C15—H15B	0.9600
N1—C3	1.467 (3)	C15—H15C	0.9600
C1—C6—C5	120.32 (18)	C2—C1—H1	119.9
C1—C6—C7	122.42 (18)	C3—C2—C1	118.3 (2)
C5—C6—C7	117.25 (19)	C3—C2—H2	120.9
N4—C8—N2	115.52 (18)	C1—C2—H2	120.9
N4—C8—S1	126.90 (15)	C13—C12—C11	121.0 (2)
N2—C8—S1	117.56 (15)	C13—C12—H12	119.5
C7—N2—C8	128.27 (18)	C11—C12—H12	119.5
C7—N2—H2'	115.9	C12—C11—C10	118.3 (2)
C8—N2—H2'	115.9	C12—C11—C15	121.7 (2)
C14—C9—C10	120.97 (18)	C10—C11—C15	120.1 (2)
C14—C9—N4	117.68 (18)	C4—C5—C6	119.7 (2)
C10—C9—N4	121.17 (19)	C4—C5—H5	120.1
O3—C7—N2	123.19 (19)	C6—C5—H5	120.1
O3—C7—C6	122.51 (19)	C3—C4—C5	118.59 (19)
N2—C7—C6	114.24 (18)	C3—C4—H4	120.7
C8—N4—C9	127.32 (17)	C5—C4—H4	120.7
C8—N4—H4'	116.3	C9—C14—C13	118.4 (2)
C9—N4—H4'	116.3	C9—C14—H14	120.8
C9—C10—C11	120.3 (2)	C13—C14—H14	120.8
C9—C10—H10	119.8	C12—C13—C14	120.9 (2)
C11—C10—H10	119.8	C12—C13—H13	119.5
O2—N1—O1	123.1 (2)	C14—C13—H13	119.5
O2—N1—C3	118.5 (2)	C11—C15—H15A	109.5
O1—N1—C3	118.3 (2)	C11—C15—H15B	109.5
C4—C3—C2	122.73 (18)	H15A—C15—H15B	109.5
C4—C3—N1	118.87 (18)	C11—C15—H15C	109.5
C2—C3—N1	118.4 (2)	H15A—C15—H15C	109.5
C6—C1—C2	120.21 (18)	H15B—C15—H15C	109.5
C6—C1—H1	119.9
N4—C8—N2—C7	9.9 (3)	C5—C6—C1—C2	3.3 (3)
S1—C8—N2—C7	−168.46 (16)	C7—C6—C1—C2	−175.48 (19)
C8—N2—C7—O3	−4.2 (3)	C4—C3—C2—C1	−3.5 (3)
C8—N2—C7—C6	173.12 (17)	N1—C3—C2—C1	175.73 (18)
C1—C6—C7—O3	−141.1 (2)	C6—C1—C2—C3	0.2 (3)
C5—C6—C7—O3	40.1 (3)	C13—C12—C11—C10	0.5 (3)
C1—C6—C7—N2	41.5 (3)	C13—C12—C11—C15	−179.4 (2)
C5—C6—C7—N2	−137.3 (2)	C9—C10—C11—C12	1.2 (3)
N2—C8—N4—C9	177.28 (17)	C9—C10—C11—C15	−178.8 (2)
S1—C8—N4—C9	−4.5 (3)	C1—C6—C5—C4	−3.6 (3)
C14—C9—N4—C8	138.7 (2)	C7—C6—C5—C4	175.16 (19)
C10—C9—N4—C8	−46.1 (3)	C2—C3—C4—C5	3.1 (3)
C14—C9—C10—C11	−2.0 (3)	N1—C3—C4—C5	−176.1 (2)
N4—C9—C10—C11	−177.11 (18)	C6—C5—C4—C3	0.5 (3)
O2—N1—C3—C4	169.0 (2)	C10—C9—C14—C13	1.0 (3)
O1—N1—C3—C4	−8.1 (3)	N4—C9—C14—C13	176.2 (2)
O2—N1—C3—C2	−10.3 (3)	C11—C12—C13—C14	−1.5 (4)
O1—N1—C3—C2	172.6 (2)	C9—C14—C13—C12	0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2'···S1i	0.86	2.81	3.665 (4)	179.
N4—H4'···O3	0.86	1.94	2.643 (3)	138.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2′⋯S1i	0.86	2.81	3.665 (4)	179
N4—H4′⋯O3	0.86	1.94	2.643 (3)	138

Symmetry code: (i) .