N-(4-Chloro-3-nitro­phen­yl)-N′-(3-nitro­benzo­yl)thio­urea

In the title mol­ecule, C₁₄H₉ClN₄O₅S, all bond lengths and angles show normal values. The mean plane of the central thio­urea unit, N₂CS, makes dihedral angles of 9.54 (12) and 56.60 (10)°, respectively, with the mean planes of the 3-nitro­benzoyl and 4-chloro-3-nitro­phenyl groups. The crystal packing is stabilized by weak inter­molecular N—H...O and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.113
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C7      ..       2.95 Ang.

   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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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

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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-(4-Chloro-3-nitrophenyl)-N'-(3-nitrobenzoyl)thiourea

Crystal data

C14H9ClN4O5S	Z = 2
Mr = 380.77	F(000) = 388
Triclinic, P1	Dx = 1.622 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7327 (14) Å	Cell parameters from 939 reflections
b = 7.8617 (14) Å	θ = 1.4–25.0°
c = 14.368 (3) Å	µ = 0.42 mm^−1
α = 102.041 (3)°	T = 298 K
β = 94.257 (3)°	Slab, light yellow
γ = 112.213 (3)°	0.40 × 0.18 × 0.11 mm
V = 779.5 (2) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2744 independent reflections
Radiation source: fine-focus sealed tube	2230 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 83.66 pixels mm^-1	θmax = 25.0°, θmin = 1.4°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −9→9
Tmin = 0.852, Tmax = 0.956	l = −17→16
7444 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0619P)^2 + 0.2966P] where P = (Fo^2 + 2Fc^2)/3
2744 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

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
Cl1	0.43686 (10)	0.25229 (10)	0.36046 (4)	0.0577 (2)
S1	0.56578 (12)	0.53667 (10)	0.85110 (5)	0.0621 (2)
O1	0.9577 (3)	−0.1878 (3)	1.22903 (13)	0.0630 (5)
O2	0.8955 (3)	−0.2921 (3)	1.07395 (13)	0.0571 (5)
O3	0.6835 (3)	0.0238 (2)	0.87269 (11)	0.0516 (5)
O4	0.0737 (3)	0.1318 (4)	0.43679 (16)	0.0973 (9)
O5	0.1218 (3)	0.3560 (4)	0.5640 (2)	0.0839 (7)
N1	0.9100 (3)	−0.1752 (3)	1.14858 (15)	0.0466 (5)
N2	0.6585 (3)	0.3032 (3)	0.93077 (13)	0.0437 (5)
H2	0.6640	0.3823	0.9834	0.052*
N3	0.6053 (3)	0.2233 (3)	0.76440 (13)	0.0440 (5)
H3	0.6299	0.1278	0.7703	0.053*
N4	0.1703 (3)	0.2456 (4)	0.51101 (17)	0.0562 (6)
C1	0.7981 (4)	0.2959 (4)	1.12319 (18)	0.0515 (6)
H1A	0.7750	0.4015	1.1177	0.062*
C2	0.8652 (5)	0.2854 (4)	1.21270 (19)	0.0645 (8)
H2A	0.8855	0.3833	1.2670	0.077*
C3	0.9021 (4)	0.1314 (4)	1.22216 (17)	0.0545 (7)
H3A	0.9478	0.1235	1.2822	0.065*
C4	0.8696 (3)	−0.0108 (3)	1.14025 (16)	0.0396 (5)
C5	0.8012 (3)	−0.0053 (3)	1.05034 (16)	0.0379 (5)
H5A	0.7795	−0.1044	0.9965	0.046*
C6	0.7651 (3)	0.1515 (3)	1.04165 (15)	0.0369 (5)
C7	0.6990 (3)	0.1523 (3)	0.94146 (16)	0.0389 (5)
C8	0.6095 (3)	0.3452 (3)	0.84544 (16)	0.0413 (5)
C9	0.5636 (3)	0.2381 (3)	0.66949 (16)	0.0396 (5)
C10	0.6924 (3)	0.2384 (4)	0.60778 (18)	0.0457 (6)
H10	0.8069	0.2351	0.6300	0.055*
C11	0.6525 (4)	0.2434 (4)	0.51309 (17)	0.0461 (6)
H11	0.7412	0.2460	0.4725	0.055*
C12	0.4822 (3)	0.2447 (3)	0.47885 (16)	0.0402 (5)
C13	0.3552 (3)	0.2448 (3)	0.54155 (16)	0.0388 (5)
C14	0.3942 (3)	0.2433 (3)	0.63644 (16)	0.0409 (5)
H14	0.3074	0.2458	0.6776	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0758 (5)	0.0687 (4)	0.0299 (3)	0.0281 (4)	0.0055 (3)	0.0183 (3)
S1	0.1013 (6)	0.0578 (4)	0.0375 (4)	0.0509 (4)	−0.0108 (3)	0.0054 (3)
O1	0.0869 (14)	0.0827 (14)	0.0433 (11)	0.0512 (12)	0.0090 (10)	0.0339 (10)
O2	0.0774 (13)	0.0509 (11)	0.0492 (11)	0.0335 (10)	0.0044 (9)	0.0133 (9)
O3	0.0804 (13)	0.0488 (10)	0.0317 (9)	0.0364 (9)	−0.0018 (8)	0.0069 (8)
O4	0.0637 (14)	0.156 (2)	0.0500 (14)	0.0279 (15)	−0.0154 (11)	0.0220 (15)
O5	0.0636 (14)	0.1029 (18)	0.1023 (19)	0.0514 (14)	0.0133 (13)	0.0276 (15)
N1	0.0529 (12)	0.0537 (12)	0.0431 (12)	0.0270 (10)	0.0076 (9)	0.0227 (10)
N2	0.0628 (13)	0.0479 (11)	0.0257 (10)	0.0319 (10)	−0.0039 (9)	0.0061 (8)
N3	0.0616 (13)	0.0491 (11)	0.0298 (10)	0.0334 (10)	−0.0005 (9)	0.0094 (9)
N4	0.0464 (13)	0.0814 (16)	0.0442 (13)	0.0241 (12)	0.0012 (11)	0.0289 (12)
C1	0.0758 (18)	0.0504 (15)	0.0362 (13)	0.0359 (14)	0.0024 (12)	0.0100 (11)
C2	0.108 (2)	0.0581 (17)	0.0318 (14)	0.0449 (17)	−0.0016 (14)	0.0033 (12)
C3	0.0790 (19)	0.0622 (16)	0.0281 (13)	0.0354 (15)	−0.0004 (12)	0.0134 (12)
C4	0.0455 (13)	0.0442 (13)	0.0349 (12)	0.0212 (11)	0.0057 (10)	0.0162 (10)
C5	0.0435 (13)	0.0406 (12)	0.0308 (12)	0.0183 (10)	0.0037 (10)	0.0099 (9)
C6	0.0428 (13)	0.0415 (12)	0.0297 (11)	0.0197 (10)	0.0050 (9)	0.0113 (9)
C7	0.0433 (13)	0.0407 (13)	0.0339 (12)	0.0190 (10)	0.0018 (10)	0.0094 (10)
C8	0.0477 (14)	0.0466 (13)	0.0306 (12)	0.0223 (11)	−0.0023 (10)	0.0088 (10)
C9	0.0499 (14)	0.0417 (13)	0.0294 (11)	0.0221 (11)	0.0003 (10)	0.0089 (9)
C10	0.0445 (14)	0.0545 (15)	0.0433 (14)	0.0261 (12)	0.0032 (11)	0.0131 (11)
C11	0.0515 (15)	0.0542 (15)	0.0387 (13)	0.0255 (12)	0.0133 (11)	0.0147 (11)
C12	0.0516 (14)	0.0381 (13)	0.0279 (11)	0.0158 (11)	0.0016 (10)	0.0087 (9)
C13	0.0398 (13)	0.0434 (13)	0.0326 (12)	0.0168 (10)	−0.0008 (10)	0.0109 (10)
C14	0.0464 (14)	0.0501 (14)	0.0298 (12)	0.0229 (11)	0.0050 (10)	0.0115 (10)

Geometric parameters (Å, º)

Cl1—C12	1.729 (2)	C2—C3	1.375 (4)
S1—C8	1.650 (2)	C2—H2A	0.9300
O1—N1	1.222 (3)	C3—C4	1.376 (3)
O2—N1	1.225 (3)	C3—H3A	0.9300
O3—C7	1.219 (3)	C4—C5	1.375 (3)
O4—N4	1.214 (3)	C5—C6	1.390 (3)
O5—N4	1.219 (3)	C5—H5A	0.9300
N1—C4	1.465 (3)	C6—C7	1.493 (3)
N2—C7	1.371 (3)	C9—C14	1.379 (3)
N2—C8	1.397 (3)	C9—C10	1.381 (3)
N2—H2	0.8600	C10—C11	1.385 (3)
N3—C8	1.334 (3)	C10—H10	0.9300
N3—C9	1.416 (3)	C11—C12	1.376 (3)
N3—H3	0.8600	C11—H11	0.9300
N4—C13	1.467 (3)	C12—C13	1.381 (3)
C1—C6	1.381 (3)	C13—C14	1.378 (3)
C1—C2	1.381 (3)	C14—H14	0.9300
C1—H1A	0.9300
O1—N1—O2	123.5 (2)	C1—C6—C5	119.2 (2)
O1—N1—C4	118.6 (2)	C1—C6—C7	124.9 (2)
O2—N1—C4	117.84 (19)	C5—C6—C7	115.84 (19)
C7—N2—C8	128.4 (2)	O3—C7—N2	122.1 (2)
C7—N2—H2	115.8	O3—C7—C6	120.7 (2)
C8—N2—H2	115.8	N2—C7—C6	117.20 (19)
C8—N3—C9	125.45 (19)	N3—C8—N2	115.1 (2)
C8—N3—H3	117.3	N3—C8—S1	125.45 (17)
C9—N3—H3	117.3	N2—C8—S1	119.48 (17)
O4—N4—O5	124.7 (3)	C14—C9—C10	119.6 (2)
O4—N4—C13	117.8 (3)	C14—C9—N3	121.4 (2)
O5—N4—C13	117.5 (2)	C10—C9—N3	119.0 (2)
C6—C1—C2	120.8 (2)	C9—C10—C11	120.6 (2)
C6—C1—H1A	119.6	C9—C10—H10	119.7
C2—C1—H1A	119.6	C11—C10—H10	119.7
C3—C2—C1	120.5 (2)	C12—C11—C10	120.3 (2)
C3—C2—H2A	119.8	C12—C11—H11	119.9
C1—C2—H2A	119.8	C10—C11—H11	119.9
C2—C3—C4	118.0 (2)	C11—C12—C13	118.4 (2)
C2—C3—H3A	121.0	C11—C12—Cl1	119.20 (19)
C4—C3—H3A	121.0	C13—C12—Cl1	122.35 (18)
C3—C4—C5	122.8 (2)	C12—C13—C14	122.0 (2)
C3—C4—N1	118.9 (2)	C12—C13—N4	122.0 (2)
C5—C4—N1	118.3 (2)	C14—C13—N4	116.0 (2)
C4—C5—C6	118.6 (2)	C9—C14—C13	119.1 (2)
C4—C5—H5A	120.7	C9—C14—H14	120.5
C6—C5—H5A	120.7	C13—C14—H14	120.5
C6—C1—C2—C3	0.6 (5)	C7—N2—C8—N3	−1.3 (4)
C1—C2—C3—C4	−0.2 (5)	C7—N2—C8—S1	179.70 (19)
C2—C3—C4—C5	−0.4 (4)	C8—N3—C9—C14	−58.3 (3)
C2—C3—C4—N1	179.4 (2)	C8—N3—C9—C10	124.7 (3)
O1—N1—C4—C3	5.4 (3)	C14—C9—C10—C11	−0.1 (4)
O2—N1—C4—C3	−173.9 (2)	N3—C9—C10—C11	176.9 (2)
O1—N1—C4—C5	−174.8 (2)	C9—C10—C11—C12	−1.2 (4)
O2—N1—C4—C5	5.9 (3)	C10—C11—C12—C13	1.3 (4)
C3—C4—C5—C6	0.7 (4)	C10—C11—C12—Cl1	179.69 (19)
N1—C4—C5—C6	−179.1 (2)	C11—C12—C13—C14	−0.1 (4)
C2—C1—C6—C5	−0.4 (4)	Cl1—C12—C13—C14	−178.43 (18)
C2—C1—C6—C7	−177.9 (3)	C11—C12—C13—N4	−179.8 (2)
C4—C5—C6—C1	−0.3 (3)	Cl1—C12—C13—N4	1.8 (3)
C4—C5—C6—C7	177.4 (2)	O4—N4—C13—C12	48.5 (3)
C8—N2—C7—O3	−5.1 (4)	O5—N4—C13—C12	−134.1 (3)
C8—N2—C7—C6	174.4 (2)	O4—N4—C13—C14	−131.2 (3)
C1—C6—C7—O3	175.8 (2)	O5—N4—C13—C14	46.1 (3)
C5—C6—C7—O3	−1.7 (3)	C10—C9—C14—C13	1.3 (3)
C1—C6—C7—N2	−3.7 (4)	N3—C9—C14—C13	−175.6 (2)
C5—C6—C7—N2	178.7 (2)	C12—C13—C14—C9	−1.2 (4)
C9—N3—C8—N2	−178.6 (2)	N4—C13—C14—C9	178.5 (2)
C9—N3—C8—S1	0.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3	0.86	1.92	2.616 (3)	138
N2—H2···O2^i	0.86	2.50	3.165 (3)	135
C1—H1A···O2^i	0.93	2.47	3.279 (4)	146
C3—H3A···O4^ii	0.93	2.34	3.264 (3)	175
C10—H10···O5^iii	0.93	2.59	3.242 (4)	128
C14—H14···O1^iv	0.93	2.48	3.401 (3)	169

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