N-(4-Methyl­benzo­yl)-N′-(4-nitro­phen­yl)thio­urea

Yusof, M.S.M.; Hamid, M.A.; Ramli, R.N.H.R.; Yamin, B.M.

doi:10.1107/S1600536806015534

N-(4-Methylbenzoyl)-N'-(4-nitrophenyl)thiourea

M. S. M. Yusof, M. A. Hamid, R. N. H. R. Ramli and B. M. Yamin

The title compound, C₁₅H₁₃N₃O₃S, adopts a trans-cis configuration of the tolyl and nitrophenyl groups, respectively, with respect to the thiono S atom across the thiourea C-N bonds. The molecule is stabilized by intermolecular hydrogen bonds, forming one-dimensional chains parallel to the a axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015534/ac2017sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015534/ac2017Isup2.hkl Contains datablock I

CCDC reference: 610674

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.046
wR factor = 0.128
Data-to-parameter ratio = 12.9

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

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   0 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

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

N-(4-Methylbenzoyl)-N-(4-nitrophenyl)thiourea top

Crystal data top

C₁₅H₁₃N₃O₃S	F(000) = 656
M_r = 315.34	D_x = 1.430 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1024 reflections
a = 12.237 (3) Å	θ = 1.7–25.0°
b = 6.3181 (15) Å	µ = 0.24 mm⁻¹
c = 19.362 (5) Å	T = 293 K
β = 101.976 (4)°	Slab, light yellow
V = 1464.4 (6) Å³	0.40 × 0.31 × 0.11 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2572 independent reflections
Radiation source: fine-focus sealed tube	2004 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.0°, θ_min = 1.7°
ω scans	h = −14→13
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −7→7
T_min = 0.911, T_max = 0.974	l = −23→21
7216 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0714P)² + 0.407P] where P = (F_o² + 2F_c²)/3
2572 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

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

	x	y	z	U_iso*/U_eq
S1	0.09616 (6)	0.64478 (12)	0.08710 (4)	0.0640 (3)
O1	0.34704 (14)	0.4156 (3)	−0.03927 (10)	0.0614 (5)
O2	0.5778 (2)	1.4744 (4)	0.18236 (12)	0.0894 (7)
O3	0.42415 (18)	1.5513 (3)	0.21375 (11)	0.0802 (6)
N1	0.18220 (15)	0.4256 (3)	−0.00226 (10)	0.0477 (5)
H1A	0.1181	0.3645	−0.0081	0.057*
N2	0.29485 (15)	0.6956 (3)	0.04981 (10)	0.0458 (5)
H2A	0.3399	0.6369	0.0269	0.055*
N3	0.4813 (2)	1.4374 (4)	0.18436 (11)	0.0588 (6)
C6	0.21069 (18)	0.1571 (3)	−0.08598 (12)	0.0428 (5)
C1	0.1307 (2)	0.0208 (4)	−0.06996 (12)	0.0489 (6)
H1	0.1018	0.0445	−0.0299	0.059*
C2	0.0938 (2)	−0.1498 (4)	−0.11304 (13)	0.0514 (6)
H2	0.0401	−0.2396	−0.1015	0.062*
C3	0.1350 (2)	−0.1894 (4)	−0.17287 (12)	0.0491 (6)
C4	0.2150 (2)	−0.0524 (4)	−0.18859 (13)	0.0564 (7)
H4	0.2437	−0.0758	−0.2288	0.068*
C5	0.2525 (2)	0.1175 (4)	−0.14587 (13)	0.0531 (6)
H5	0.3066	0.2066	−0.1573	0.064*
C15	0.0941 (3)	−0.3753 (4)	−0.21946 (15)	0.0690 (8)
H15C	0.0430	−0.4568	−0.1987	0.104*
H15B	0.1564	−0.4623	−0.2243	0.104*
H15A	0.0568	−0.3257	−0.2651	0.104*
C7	0.25433 (19)	0.3412 (4)	−0.04129 (12)	0.0455 (6)
C8	0.19740 (19)	0.5943 (4)	0.04499 (12)	0.0452 (6)
C9	0.33626 (18)	0.8819 (3)	0.08604 (12)	0.0425 (5)
C10	0.4417 (2)	0.9428 (4)	0.07917 (13)	0.0531 (6)
H10	0.4811	0.8599	0.0530	0.064*
C11	0.4890 (2)	1.1250 (4)	0.11072 (14)	0.0564 (7)
H11	0.5599	1.1662	0.1059	0.068*
C12	0.4307 (2)	1.2450 (4)	0.14926 (12)	0.0469 (6)
C13	0.3261 (2)	1.1885 (4)	0.15708 (14)	0.0573 (7)
H13	0.2878	1.2721	0.1837	0.069*
C14	0.2781 (2)	1.0062 (4)	0.12518 (14)	0.0578 (7)
H14	0.2068	0.9668	0.1299	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0576 (4)	0.0738 (5)	0.0673 (5)	−0.0202 (3)	0.0283 (3)	−0.0246 (4)
O1	0.0499 (10)	0.0622 (12)	0.0753 (12)	−0.0107 (9)	0.0205 (9)	−0.0229 (9)
O2	0.0970 (16)	0.0814 (16)	0.0953 (16)	−0.0481 (13)	0.0329 (13)	−0.0261 (12)
O3	0.0948 (15)	0.0609 (13)	0.0800 (14)	−0.0023 (11)	0.0069 (12)	−0.0300 (11)
N1	0.0448 (11)	0.0442 (11)	0.0558 (12)	−0.0093 (8)	0.0147 (9)	−0.0098 (9)
N2	0.0418 (10)	0.0437 (11)	0.0531 (12)	−0.0047 (8)	0.0126 (9)	−0.0099 (9)
N3	0.0731 (15)	0.0521 (14)	0.0477 (13)	−0.0149 (12)	0.0043 (11)	−0.0019 (10)
C6	0.0449 (12)	0.0375 (12)	0.0451 (13)	0.0008 (10)	0.0075 (10)	0.0001 (10)
C1	0.0618 (15)	0.0383 (13)	0.0487 (14)	−0.0020 (11)	0.0160 (11)	−0.0006 (11)
C2	0.0590 (15)	0.0371 (13)	0.0589 (15)	−0.0085 (11)	0.0140 (12)	0.0037 (11)
C3	0.0578 (14)	0.0383 (13)	0.0481 (14)	0.0011 (11)	0.0039 (12)	−0.0004 (11)
C4	0.0642 (16)	0.0569 (16)	0.0507 (14)	−0.0035 (13)	0.0181 (12)	−0.0064 (12)
C5	0.0530 (14)	0.0487 (15)	0.0601 (16)	−0.0102 (12)	0.0174 (12)	−0.0079 (12)
C15	0.092 (2)	0.0515 (16)	0.0617 (17)	−0.0125 (15)	0.0126 (15)	−0.0117 (13)
C7	0.0460 (13)	0.0411 (13)	0.0484 (13)	−0.0020 (11)	0.0076 (11)	0.0010 (10)
C8	0.0499 (13)	0.0409 (13)	0.0439 (13)	−0.0042 (10)	0.0077 (10)	−0.0025 (10)
C9	0.0456 (13)	0.0379 (12)	0.0423 (12)	−0.0009 (10)	0.0057 (10)	−0.0016 (10)
C10	0.0489 (14)	0.0519 (15)	0.0606 (16)	−0.0058 (11)	0.0161 (12)	−0.0130 (12)
C11	0.0501 (14)	0.0580 (16)	0.0613 (16)	−0.0131 (12)	0.0124 (12)	−0.0050 (13)
C12	0.0579 (15)	0.0400 (13)	0.0386 (12)	−0.0030 (11)	0.0004 (11)	−0.0022 (10)
C13	0.0621 (16)	0.0524 (16)	0.0596 (16)	−0.0019 (12)	0.0176 (13)	−0.0161 (12)
C14	0.0496 (14)	0.0569 (16)	0.0701 (17)	−0.0088 (12)	0.0194 (13)	−0.0168 (13)

Geometric parameters (Å, º) top

S1—C8	1.649 (2)	C3—C4	1.387 (3)
O1—C7	1.221 (3)	C3—C15	1.502 (3)
O2—N3	1.212 (3)	C4—C5	1.374 (3)
O3—N3	1.223 (3)	C4—H4	0.9300
N1—C7	1.383 (3)	C5—H5	0.9300
N1—C8	1.392 (3)	C15—H15C	0.9600
N1—H1A	0.8600	C15—H15B	0.9600
N2—C8	1.339 (3)	C15—H15A	0.9600
N2—C9	1.410 (3)	C9—C10	1.379 (3)
N2—H2A	0.8600	C9—C14	1.386 (3)
N3—C12	1.466 (3)	C10—C11	1.373 (3)
C6—C5	1.384 (3)	C10—H10	0.9300
C6—C1	1.386 (3)	C11—C12	1.364 (3)
C6—C7	1.481 (3)	C11—H11	0.9300
C1—C2	1.380 (3)	C12—C13	1.367 (3)
C1—H1	0.9300	C13—C14	1.379 (3)
C2—C3	1.379 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300

C7—N1—C8	129.90 (19)	H15C—C15—H15B	109.5
C7—N1—H1A	115.1	C3—C15—H15A	109.5
C8—N1—H1A	115.1	H15C—C15—H15A	109.5
C8—N2—C9	131.04 (19)	H15B—C15—H15A	109.5
C8—N2—H2A	114.5	O1—C7—N1	121.9 (2)
C9—N2—H2A	114.5	O1—C7—C6	122.7 (2)
O2—N3—O3	123.8 (2)	N1—C7—C6	115.37 (19)
O2—N3—C12	117.7 (2)	N2—C8—N1	114.04 (19)
O3—N3—C12	118.5 (2)	N2—C8—S1	128.49 (18)
C5—C6—C1	118.4 (2)	N1—C8—S1	117.48 (16)
C5—C6—C7	118.7 (2)	C10—C9—C14	119.5 (2)
C1—C6—C7	122.9 (2)	C10—C9—N2	115.6 (2)
C2—C1—C6	120.5 (2)	C14—C9—N2	124.9 (2)
C2—C1—H1	119.7	C11—C10—C9	120.5 (2)
C6—C1—H1	119.7	C11—C10—H10	119.8
C3—C2—C1	121.2 (2)	C9—C10—H10	119.8
C3—C2—H2	119.4	C12—C11—C10	119.3 (2)
C1—C2—H2	119.4	C12—C11—H11	120.3
C2—C3—C4	117.9 (2)	C10—C11—H11	120.3
C2—C3—C15	120.8 (2)	C11—C12—C13	121.5 (2)
C4—C3—C15	121.2 (2)	C11—C12—N3	119.8 (2)
C5—C4—C3	121.2 (2)	C13—C12—N3	118.7 (2)
C5—C4—H4	119.4	C12—C13—C14	119.4 (2)
C3—C4—H4	119.4	C12—C13—H13	120.3
C4—C5—C6	120.7 (2)	C14—C13—H13	120.3
C4—C5—H5	119.7	C13—C14—C9	119.9 (2)
C6—C5—H5	119.7	C13—C14—H14	120.1
C3—C15—H15C	109.5	C9—C14—H14	120.1
C3—C15—H15B	109.5

C5—C6—C1—C2	−0.2 (4)	C7—N1—C8—N2	4.1 (3)
C7—C6—C1—C2	−179.3 (2)	C7—N1—C8—S1	−176.05 (19)
C6—C1—C2—C3	0.0 (4)	C8—N2—C9—C10	−179.7 (2)
C1—C2—C3—C4	0.0 (4)	C8—N2—C9—C14	−1.5 (4)
C1—C2—C3—C15	−179.9 (2)	C14—C9—C10—C11	0.0 (4)
C2—C3—C4—C5	0.2 (4)	N2—C9—C10—C11	178.3 (2)
C15—C3—C4—C5	−179.9 (2)	C9—C10—C11—C12	0.3 (4)
C3—C4—C5—C6	−0.4 (4)	C10—C11—C12—C13	−0.2 (4)
C1—C6—C5—C4	0.4 (4)	C10—C11—C12—N3	178.8 (2)
C7—C6—C5—C4	179.6 (2)	O2—N3—C12—C11	−5.8 (3)
C8—N1—C7—O1	−1.7 (4)	O3—N3—C12—C11	174.1 (2)
C8—N1—C7—C6	179.1 (2)	O2—N3—C12—C13	173.2 (2)
C5—C6—C7—O1	−25.5 (3)	O3—N3—C12—C13	−6.9 (3)
C1—C6—C7—O1	153.6 (2)	C11—C12—C13—C14	−0.2 (4)
C5—C6—C7—N1	153.8 (2)	N3—C12—C13—C14	−179.1 (2)
C1—C6—C7—N1	−27.1 (3)	C12—C13—C14—C9	0.4 (4)
C9—N2—C8—N1	173.5 (2)	C10—C9—C14—C13	−0.3 (4)
C9—N2—C8—S1	−6.3 (4)	N2—C9—C14—C13	−178.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.91	2.640 (3)	142
C14—H14···S1	0.93	2.49	3.168 (3)	130
N1—H1A···S1ⁱ	0.86	2.75	3.490 (2)	145
C5—H5···O2ⁱⁱ	0.93	2.57	3.474 (4)	165

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

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N-(4-Methyl­benzo­yl)-N'-(4-nitro­phen­yl)thio­urea

Supporting information

Key indicators

checkCIF/PLATON results

N-(4-Methylbenzoyl)-N'-(4-nitrophenyl)thiourea