N-(3,4-Dichloro­phen­yl)-N′-(3-nitro­benzo­yl)thio­urea

In the title mol­ecule, C₁₄H₉N₃O₃Cl₂S, the dihedral angles between the mean plane of the central carbonyl­thio­urea group, N₂CSCO, and the mean planes of the 3-nitro­benzoyl and 3,4-dichloro­phenyl groups are 22.82 (9) and 69.75 (11)°, respectively. The crystal packing is stabilized by weak inter­molecular C—H...O hydrogen bonds, forming a one-dimensional chain along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.105
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
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    O2     -   N1      ..       5.05 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.15
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2B    ...          ?

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

   2 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

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-(3,4-dichlorophenyl)-N'-(3-nitrobenzoyl)thiourea

Crystal data

C14H9Cl2N3O3S	Z = 2
Mr = 370.20	F(000) = 376
Triclinic, P1	Dx = 1.613 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1648 (15) Å	Cell parameters from 881 reflections
b = 8.1522 (17) Å	θ = 1.5–26.0°
c = 13.866 (3) Å	µ = 0.58 mm^−1
α = 73.990 (3)°	T = 293 K
β = 81.912 (3)°	Slab, light yellow
γ = 79.552 (4)°	0.50 × 0.22 × 0.08 mm
V = 762.0 (3) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2964 independent reflections
Radiation source: fine-focus sealed tube	2400 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 83.66 pixels mm^-1	θmax = 26.0°, θmin = 1.5°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −10→10
Tmin = 0.760, Tmax = 0.955	l = −17→17
7867 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0508P)^2 + 0.2184P] where P = (Fo^2 + 2Fc^2)/3
2964 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl1	−0.04834 (10)	−0.37658 (9)	0.65598 (4)	0.0642 (2)
Cl2	−0.32204 (10)	−0.34234 (10)	0.48877 (5)	0.0668 (2)
S1	0.08504 (11)	−0.21577 (9)	0.13950 (4)	0.0567 (2)
O1	0.4247 (3)	0.8699 (3)	−0.27091 (17)	0.0867 (7)
O2	0.3228 (4)	0.8584 (3)	−0.1169 (2)	0.1049 (9)
O3	0.2332 (3)	0.3104 (2)	0.12332 (12)	0.0642 (5)
N1	0.3725 (3)	0.7910 (3)	−0.18561 (19)	0.0646 (6)
N2	0.1913 (3)	0.0890 (3)	0.06250 (13)	0.0518 (5)
H2B	0.1949	0.0597	0.0072	0.062*
N3	0.1403 (3)	0.0113 (3)	0.23555 (13)	0.0500 (5)
H3	0.1726	0.1104	0.2300	0.060*
C1	0.3751 (3)	0.2600 (3)	−0.12787 (17)	0.0477 (6)
H1A	0.3763	0.1417	−0.1151	0.057*
C2	0.4418 (4)	0.3512 (3)	−0.22188 (17)	0.0534 (6)
H2A	0.4881	0.2943	−0.2720	0.064*
C3	0.4400 (3)	0.5259 (3)	−0.24168 (17)	0.0490 (6)
H3A	0.4845	0.5888	−0.3049	0.059*
C4	0.3713 (3)	0.6050 (3)	−0.16635 (17)	0.0447 (6)
C5	0.3051 (3)	0.5175 (3)	−0.07125 (17)	0.0440 (5)
H5	0.2607	0.5753	−0.0213	0.053*
C6	0.3063 (3)	0.3422 (3)	−0.05208 (15)	0.0405 (5)
C7	0.2392 (3)	0.2490 (3)	0.05194 (17)	0.0467 (6)
C8	0.1375 (3)	−0.0331 (3)	0.14994 (16)	0.0456 (6)
C9	0.0951 (3)	−0.0894 (3)	0.33518 (15)	0.0433 (5)
C10	0.2133 (3)	−0.1012 (3)	0.40786 (16)	0.0470 (6)
H10	0.3232	−0.0496	0.3908	0.056*
C11	0.1677 (3)	−0.1901 (3)	0.50621 (17)	0.0490 (6)
H11	0.2475	−0.1983	0.5553	0.059*
C12	0.0057 (3)	−0.2663 (3)	0.53222 (15)	0.0447 (6)
C13	−0.1127 (3)	−0.2527 (3)	0.45906 (16)	0.0447 (6)
C14	−0.0695 (3)	−0.1641 (3)	0.36069 (16)	0.0463 (6)
H14	−0.1504	−0.1547	0.3119	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0800 (5)	0.0692 (4)	0.0298 (3)	−0.0126 (4)	0.0055 (3)	0.0055 (3)
Cl2	0.0604 (4)	0.0880 (5)	0.0484 (4)	−0.0310 (4)	0.0129 (3)	−0.0075 (3)
S1	0.0810 (5)	0.0580 (4)	0.0346 (3)	−0.0369 (3)	0.0002 (3)	−0.0035 (3)
O1	0.1008 (17)	0.0543 (12)	0.0803 (14)	−0.0221 (11)	0.0072 (12)	0.0226 (10)
O2	0.154 (2)	0.0455 (12)	0.108 (2)	−0.0249 (13)	0.0417 (17)	−0.0274 (13)
O3	0.1043 (15)	0.0566 (11)	0.0331 (9)	−0.0315 (10)	0.0096 (9)	−0.0092 (8)
N1	0.0659 (15)	0.0405 (12)	0.0730 (16)	−0.0124 (11)	0.0074 (12)	0.0050 (12)
N2	0.0762 (15)	0.0567 (12)	0.0254 (9)	−0.0343 (11)	−0.0015 (9)	−0.0012 (8)
N3	0.0728 (14)	0.0500 (11)	0.0272 (10)	−0.0279 (10)	0.0010 (9)	−0.0008 (8)
C1	0.0563 (15)	0.0426 (13)	0.0435 (13)	−0.0161 (11)	0.0033 (11)	−0.0082 (10)
C2	0.0639 (17)	0.0601 (16)	0.0367 (13)	−0.0161 (13)	0.0075 (11)	−0.0150 (11)
C3	0.0517 (14)	0.0563 (15)	0.0311 (12)	−0.0145 (11)	0.0047 (10)	0.0014 (10)
C4	0.0472 (14)	0.0363 (12)	0.0437 (13)	−0.0102 (10)	0.0002 (10)	0.0014 (10)
C5	0.0492 (13)	0.0441 (13)	0.0369 (12)	−0.0128 (10)	0.0034 (10)	−0.0075 (10)
C6	0.0460 (13)	0.0436 (13)	0.0304 (11)	−0.0159 (10)	−0.0003 (9)	−0.0027 (9)
C7	0.0576 (15)	0.0482 (14)	0.0310 (12)	−0.0178 (11)	−0.0006 (10)	−0.0005 (10)
C8	0.0544 (14)	0.0508 (14)	0.0285 (11)	−0.0203 (11)	−0.0013 (10)	0.0015 (10)
C9	0.0546 (14)	0.0433 (12)	0.0273 (11)	−0.0105 (11)	0.0035 (10)	−0.0031 (9)
C10	0.0521 (14)	0.0517 (14)	0.0348 (12)	−0.0141 (11)	0.0005 (10)	−0.0054 (10)
C11	0.0560 (15)	0.0540 (14)	0.0338 (12)	−0.0047 (12)	−0.0063 (10)	−0.0072 (11)
C12	0.0566 (15)	0.0419 (13)	0.0257 (11)	−0.0010 (11)	0.0049 (10)	−0.0008 (9)
C13	0.0485 (14)	0.0446 (13)	0.0350 (12)	−0.0095 (11)	0.0094 (10)	−0.0053 (10)
C14	0.0509 (14)	0.0514 (14)	0.0330 (12)	−0.0103 (11)	−0.0016 (10)	−0.0047 (10)

Geometric parameters (Å, º)

Cl1—C12	1.730 (2)	C2—H2A	0.9300
Cl2—C13	1.735 (2)	C3—C4	1.364 (3)
S1—C8	1.648 (2)	C3—H3A	0.9300
O1—N1	1.223 (3)	C4—C5	1.378 (3)
O2—N1	1.207 (3)	C5—C6	1.378 (3)
O3—C7	1.219 (3)	C5—H5	0.9300
N1—C4	1.467 (3)	C6—C7	1.491 (3)
N2—C7	1.372 (3)	C9—C10	1.378 (3)
N2—C8	1.397 (3)	C9—C14	1.383 (3)
N2—H2B	0.8600	C10—C11	1.381 (3)
N3—C8	1.337 (3)	C10—H10	0.9300
N3—C9	1.426 (3)	C11—C12	1.372 (3)
N3—H3	0.8600	C11—H11	0.9300
C1—C2	1.378 (3)	C12—C13	1.381 (3)
C1—C6	1.386 (3)	C13—C14	1.377 (3)
C1—H1A	0.9300	C14—H14	0.9300
C2—C3	1.372 (3)
O2—N1—O1	123.3 (2)	C1—C6—C7	123.1 (2)
O2—N1—C4	118.7 (2)	O3—C7—N2	122.5 (2)
O1—N1—C4	118.0 (3)	O3—C7—C6	121.4 (2)
C7—N2—C8	129.5 (2)	N2—C7—C6	116.1 (2)
C7—N2—H2B	115.3	N3—C8—N2	114.6 (2)
C8—N2—H2B	115.3	N3—C8—S1	126.61 (16)
C8—N3—C9	126.4 (2)	N2—C8—S1	118.80 (17)
C8—N3—H3	116.8	C10—C9—C14	120.3 (2)
C9—N3—H3	116.8	C10—C9—N3	118.2 (2)
C2—C1—C6	120.9 (2)	C14—C9—N3	121.3 (2)
C2—C1—H1A	119.6	C9—C10—C11	119.6 (2)
C6—C1—H1A	119.6	C9—C10—H10	120.2
C3—C2—C1	120.1 (2)	C11—C10—H10	120.2
C3—C2—H2A	120.0	C12—C11—C10	120.6 (2)
C1—C2—H2A	120.0	C12—C11—H11	119.7
C4—C3—C2	118.3 (2)	C10—C11—H11	119.7
C4—C3—H3A	120.8	C11—C12—C13	119.4 (2)
C2—C3—H3A	120.8	C11—C12—Cl1	119.72 (18)
C3—C4—C5	123.1 (2)	C13—C12—Cl1	120.89 (19)
C3—C4—N1	119.0 (2)	C14—C13—C12	120.7 (2)
C5—C4—N1	117.9 (2)	C14—C13—Cl2	118.17 (19)
C4—C5—C6	118.2 (2)	C12—C13—Cl2	121.12 (17)
C4—C5—H5	120.9	C13—C14—C9	119.4 (2)
C6—C5—H5	120.9	C13—C14—H14	120.3
C5—C6—C1	119.4 (2)	C9—C14—H14	120.3
C5—C6—C7	117.5 (2)
C6—C1—C2—C3	−0.3 (4)	C9—N3—C8—N2	−179.0 (2)
C1—C2—C3—C4	0.1 (4)	C9—N3—C8—S1	−1.2 (4)
C2—C3—C4—C5	0.5 (4)	C7—N2—C8—N3	−2.7 (4)
C2—C3—C4—N1	178.6 (2)	C7—N2—C8—S1	179.3 (2)
O2—N1—C4—C3	−175.4 (3)	C8—N3—C9—C10	135.4 (3)
O1—N1—C4—C3	4.4 (4)	C8—N3—C9—C14	−49.0 (3)
O2—N1—C4—C5	2.8 (4)	C14—C9—C10—C11	0.8 (4)
O1—N1—C4—C5	−177.4 (2)	N3—C9—C10—C11	176.5 (2)
C3—C4—C5—C6	−0.9 (4)	C9—C10—C11—C12	−0.1 (4)
N1—C4—C5—C6	−179.0 (2)	C10—C11—C12—C13	−0.3 (4)
C4—C5—C6—C1	0.6 (3)	C10—C11—C12—Cl1	−179.91 (18)
C4—C5—C6—C7	178.4 (2)	C11—C12—C13—C14	0.1 (4)
C2—C1—C6—C5	−0.1 (4)	Cl1—C12—C13—C14	179.72 (18)
C2—C1—C6—C7	−177.7 (2)	C11—C12—C13—Cl2	−178.42 (18)
C8—N2—C7—O3	−3.0 (4)	Cl1—C12—C13—Cl2	1.2 (3)
C8—N2—C7—C6	175.0 (2)	C12—C13—C14—C9	0.5 (4)
C5—C6—C7—O3	−19.6 (4)	Cl2—C13—C14—C9	179.11 (18)
C1—C6—C7—O3	158.0 (3)	C10—C9—C14—C13	−1.0 (4)
C5—C6—C7—N2	162.4 (2)	N3—C9—C14—C13	−176.6 (2)
C1—C6—C7—N2	−19.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3	0.86	1.94	2.648 (3)	138
C14—H14···S1	0.93	2.83	3.225 (2)	107
C1—H1A···O2^i	0.93	2.42	3.322 (4)	165

Symmetry code: (i) x, y−1, z.