organic compounds
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—HO hydrogen bonds, forming a one-dimensional chain along the b axis.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015996/at2032sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015996/at2032Isup2.hkl |
CCDC reference: 610686
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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 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-(3,4-dichlorophenyl)-N'-(3-nitrobenzoyl)thiourea top
Crystal data top
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) Å3 |
Data collection top
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 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0508P)2 + 0.2184P] where P = (Fo2 + 2Fc2)/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 (Å2) top
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
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) top
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) top
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···O2i | 0.93 | 2.42 | 3.322 (4) | 165 |
Symmetry code: (i) x, y−1, z. |