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The title compound, C
15H
11Cl
2N
3O
2S, has a similar structure and similar structural dimensions to the unsubstituted
N-(
N-benzoylhydrazinocarbothioyl)benzamide. However, the presence of Cl atoms at the
para and
ortho positions in the benzamide and benzoyl groups, respectively, caused the dihedral angle between these groups to increase from 16.42 (14)° in the unsubstituted compound to 74.96 (8)°. The molecule is stabilized by intermolecular C—H
O and N—H
S interactions, forming polymeric chains parallel to the
c axis.
Supporting information
CCDC reference: 251763
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.112
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
2-Chloro-
N-[
N-(4-chlorobenzoyl)hydrazinocarbothioyl]benzamide
top
Crystal data top
C15H11Cl2N3O2S | Z = 2 |
Mr = 368.24 | F(000) = 376 |
Triclinic, P1 | Dx = 1.488 Mg m−3 |
a = 7.498 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.449 (2) Å | Cell parameters from 936 reflections |
c = 11.861 (2) Å | θ = 1.9–27.0° |
α = 110.37 (1)° | µ = 0.53 mm−1 |
β = 104.62 (1)° | T = 273 K |
γ = 96.57 (1)° | Block, colourless |
V = 821.7 (3) Å3 | 0.48 × 0.37 × 0.17 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3549 independent reflections |
Radiation source: fine-focus sealed tube | 3216 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
Detector resolution: 83.66 pixels mm-1 | θmax = 27.0°, θmin = 1.9° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −13→13 |
Tmin = 0.783, Tmax = 0.914 | l = −15→15 |
9062 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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0581P)2 + 0.2898P] where P = (Fo2 + 2Fc2)/3 |
3549 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | −0.06292 (11) | 0.58378 (7) | 0.25233 (6) | 0.0819 (2) | |
Cl2 | 1.32032 (8) | 1.39958 (7) | 0.35832 (6) | 0.07327 (19) | |
S1 | 0.28522 (6) | 1.08971 (5) | 0.52002 (4) | 0.05016 (15) | |
O1 | −0.01934 (19) | 0.83714 (16) | 0.09960 (12) | 0.0604 (4) | |
O2 | 0.40628 (19) | 1.07690 (16) | 0.12321 (12) | 0.0560 (3) | |
N1 | 0.0105 (2) | 0.91866 (16) | 0.31002 (13) | 0.0449 (3) | |
H1A | −0.0518 | 0.9185 | 0.3617 | 0.054* | |
N2 | 0.2808 (2) | 1.00622 (17) | 0.28151 (14) | 0.0484 (4) | |
H2A | 0.2232 | 0.9597 | 0.2020 | 0.058* | |
N3 | 0.4630 (2) | 1.08168 (17) | 0.31907 (14) | 0.0489 (4) | |
H3A | 0.5371 | 1.1094 | 0.3954 | 0.059* | |
C1 | −0.4337 (3) | 0.7730 (2) | 0.1059 (2) | 0.0566 (5) | |
H1B | −0.4313 | 0.8465 | 0.0787 | 0.068* | |
C2 | −0.6053 (3) | 0.6916 (3) | 0.0897 (2) | 0.0737 (7) | |
H2B | −0.7181 | 0.7113 | 0.0529 | 0.088* | |
C3 | −0.6082 (4) | 0.5819 (3) | 0.1283 (3) | 0.0815 (8) | |
H3B | −0.7234 | 0.5294 | 0.1196 | 0.098* | |
C4 | −0.4433 (4) | 0.5488 (3) | 0.1795 (2) | 0.0740 (7) | |
H4A | −0.4462 | 0.4724 | 0.2027 | 0.089* | |
C5 | −0.2734 (3) | 0.6302 (2) | 0.19605 (17) | 0.0539 (5) | |
C6 | −0.2661 (3) | 0.74443 (18) | 0.16245 (15) | 0.0437 (4) | |
C7 | −0.0809 (3) | 0.83571 (19) | 0.18490 (16) | 0.0445 (4) | |
C8 | 0.1912 (2) | 1.00261 (18) | 0.36303 (15) | 0.0415 (4) | |
C9 | 0.5189 (2) | 1.10976 (18) | 0.22835 (15) | 0.0423 (4) | |
C10 | 0.7205 (2) | 1.18020 (17) | 0.26557 (15) | 0.0412 (4) | |
C11 | 0.8027 (3) | 1.16219 (19) | 0.16976 (16) | 0.0475 (4) | |
H11A | 0.7317 | 1.1063 | 0.0863 | 0.057* | |
C12 | 0.9887 (3) | 1.2267 (2) | 0.19768 (18) | 0.0515 (4) | |
H12A | 1.0442 | 1.2140 | 0.1339 | 0.062* | |
C13 | 1.0902 (3) | 1.30989 (19) | 0.32139 (18) | 0.0477 (4) | |
C14 | 1.0127 (3) | 1.3272 (2) | 0.41784 (18) | 0.0533 (4) | |
H14A | 1.0849 | 1.3824 | 0.5012 | 0.064* | |
C15 | 0.8276 (3) | 1.2621 (2) | 0.38984 (17) | 0.0510 (4) | |
H15A | 0.7744 | 1.2732 | 0.4545 | 0.061* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.1072 (5) | 0.0828 (4) | 0.0704 (4) | 0.0421 (4) | 0.0248 (3) | 0.0427 (3) |
Cl2 | 0.0501 (3) | 0.0782 (4) | 0.0798 (4) | −0.0058 (3) | 0.0179 (3) | 0.0253 (3) |
S1 | 0.0445 (3) | 0.0671 (3) | 0.0331 (2) | 0.0077 (2) | 0.01247 (17) | 0.0141 (2) |
O1 | 0.0542 (8) | 0.0831 (10) | 0.0340 (6) | −0.0002 (7) | 0.0169 (6) | 0.0139 (6) |
O2 | 0.0503 (7) | 0.0751 (9) | 0.0378 (6) | 0.0034 (6) | 0.0099 (6) | 0.0224 (6) |
N1 | 0.0426 (8) | 0.0567 (9) | 0.0343 (7) | 0.0068 (6) | 0.0170 (6) | 0.0143 (6) |
N2 | 0.0433 (8) | 0.0629 (9) | 0.0340 (7) | 0.0024 (7) | 0.0134 (6) | 0.0153 (7) |
N3 | 0.0403 (8) | 0.0660 (10) | 0.0373 (7) | 0.0020 (7) | 0.0112 (6) | 0.0204 (7) |
C1 | 0.0507 (11) | 0.0504 (10) | 0.0572 (11) | 0.0105 (8) | 0.0139 (9) | 0.0101 (9) |
C2 | 0.0470 (11) | 0.0755 (15) | 0.0732 (15) | 0.0067 (10) | 0.0188 (10) | 0.0017 (12) |
C3 | 0.0689 (15) | 0.0781 (16) | 0.0755 (16) | −0.0161 (13) | 0.0404 (13) | 0.0019 (13) |
C4 | 0.0984 (19) | 0.0609 (13) | 0.0629 (14) | −0.0029 (12) | 0.0429 (13) | 0.0188 (11) |
C5 | 0.0704 (12) | 0.0540 (10) | 0.0394 (9) | 0.0132 (9) | 0.0232 (9) | 0.0167 (8) |
C6 | 0.0484 (9) | 0.0433 (9) | 0.0339 (8) | 0.0070 (7) | 0.0160 (7) | 0.0075 (7) |
C7 | 0.0457 (9) | 0.0512 (10) | 0.0365 (8) | 0.0116 (7) | 0.0151 (7) | 0.0155 (7) |
C8 | 0.0416 (8) | 0.0495 (9) | 0.0362 (8) | 0.0126 (7) | 0.0149 (7) | 0.0174 (7) |
C9 | 0.0468 (9) | 0.0445 (9) | 0.0355 (8) | 0.0095 (7) | 0.0151 (7) | 0.0143 (7) |
C10 | 0.0451 (9) | 0.0424 (8) | 0.0367 (8) | 0.0073 (7) | 0.0138 (7) | 0.0164 (7) |
C11 | 0.0522 (10) | 0.0530 (10) | 0.0341 (8) | 0.0042 (8) | 0.0138 (7) | 0.0153 (7) |
C12 | 0.0549 (11) | 0.0575 (11) | 0.0450 (10) | 0.0067 (8) | 0.0227 (8) | 0.0202 (8) |
C13 | 0.0441 (9) | 0.0464 (9) | 0.0521 (10) | 0.0053 (7) | 0.0138 (8) | 0.0211 (8) |
C14 | 0.0531 (10) | 0.0549 (11) | 0.0392 (9) | 0.0013 (8) | 0.0083 (8) | 0.0113 (8) |
C15 | 0.0566 (11) | 0.0565 (11) | 0.0368 (9) | 0.0068 (8) | 0.0189 (8) | 0.0136 (8) |
Geometric parameters (Å, º) top
Cl1—C5 | 1.744 (2) | C3—C4 | 1.372 (4) |
Cl2—C13 | 1.7350 (19) | C3—H3B | 0.9300 |
S1—C8 | 1.6743 (17) | C4—C5 | 1.376 (3) |
O1—C7 | 1.217 (2) | C4—H4A | 0.9300 |
O2—C9 | 1.221 (2) | C5—C6 | 1.383 (3) |
N1—C7 | 1.371 (2) | C6—C7 | 1.497 (2) |
N1—C8 | 1.384 (2) | C9—C10 | 1.485 (2) |
N1—H1A | 0.8600 | C10—C15 | 1.385 (2) |
N2—C8 | 1.317 (2) | C10—C11 | 1.392 (2) |
N2—N3 | 1.375 (2) | C11—C12 | 1.380 (3) |
N2—H2A | 0.8600 | C11—H11A | 0.9300 |
N3—C9 | 1.356 (2) | C12—C13 | 1.373 (3) |
N3—H3A | 0.8600 | C12—H12A | 0.9300 |
C1—C6 | 1.385 (3) | C13—C14 | 1.376 (3) |
C1—C2 | 1.388 (3) | C14—C15 | 1.376 (3) |
C1—H1B | 0.9300 | C14—H14A | 0.9300 |
C2—C3 | 1.374 (4) | C15—H15A | 0.9300 |
C2—H2B | 0.9300 | | |
| | | |
C7—N1—C8 | 127.72 (14) | O1—C7—N1 | 123.42 (16) |
C7—N1—H1A | 116.1 | O1—C7—C6 | 122.95 (16) |
C8—N1—H1A | 116.1 | N1—C7—C6 | 113.62 (14) |
C8—N2—N3 | 122.31 (15) | N2—C8—N1 | 115.09 (15) |
C8—N2—H2A | 118.8 | N2—C8—S1 | 123.83 (14) |
N3—N2—H2A | 118.8 | N1—C8—S1 | 121.08 (12) |
C9—N3—N2 | 115.92 (14) | O2—C9—N3 | 120.23 (16) |
C9—N3—H3A | 122.0 | O2—C9—C10 | 123.77 (15) |
N2—N3—H3A | 122.0 | N3—C9—C10 | 116.01 (15) |
C6—C1—C2 | 119.8 (2) | C15—C10—C11 | 119.47 (16) |
C6—C1—H1B | 120.1 | C15—C10—C9 | 122.95 (15) |
C2—C1—H1B | 120.1 | C11—C10—C9 | 117.58 (15) |
C3—C2—C1 | 119.9 (2) | C12—C11—C10 | 120.51 (16) |
C3—C2—H2B | 120.0 | C12—C11—H11A | 119.7 |
C1—C2—H2B | 120.0 | C10—C11—H11A | 119.7 |
C4—C3—C2 | 120.8 (2) | C13—C12—C11 | 118.75 (16) |
C4—C3—H3B | 119.6 | C13—C12—H12A | 120.6 |
C2—C3—H3B | 119.6 | C11—C12—H12A | 120.6 |
C3—C4—C5 | 119.1 (2) | C12—C13—C14 | 121.68 (17) |
C3—C4—H4A | 120.5 | C12—C13—Cl2 | 119.79 (15) |
C5—C4—H4A | 120.5 | C14—C13—Cl2 | 118.51 (15) |
C4—C5—C6 | 121.3 (2) | C15—C14—C13 | 119.43 (17) |
C4—C5—Cl1 | 119.70 (18) | C15—C14—H14A | 120.3 |
C6—C5—Cl1 | 118.90 (16) | C13—C14—H14A | 120.3 |
C5—C6—C1 | 118.95 (18) | C14—C15—C10 | 120.13 (17) |
C5—C6—C7 | 121.13 (17) | C14—C15—H15A | 119.9 |
C1—C6—C7 | 119.91 (17) | C10—C15—H15A | 119.9 |
| | | |
C7—N1—C8—N2 | 3.0 (3) | C1—C6—C7—N1 | 108.71 (19) |
C7—N1—C8—S1 | −176.17 (15) | N2—N3—C9—O2 | 4.9 (3) |
C8—N2—N3—C9 | −161.68 (17) | N2—N3—C9—C10 | −174.80 (15) |
C6—C1—C2—C3 | −0.9 (3) | N3—N2—C8—N1 | −178.28 (15) |
C1—C2—C3—C4 | −1.9 (4) | N3—N2—C8—S1 | 0.8 (3) |
C2—C3—C4—C5 | 2.3 (4) | O2—C9—C10—C15 | 155.20 (19) |
C3—C4—C5—C6 | 0.2 (3) | N3—C9—C10—C15 | −25.1 (3) |
C3—C4—C5—Cl1 | −176.28 (17) | O2—C9—C10—C11 | −24.5 (3) |
C4—C5—C6—C1 | −2.9 (3) | N3—C9—C10—C11 | 155.11 (17) |
Cl1—C5—C6—C1 | 173.55 (14) | C15—C10—C11—C12 | −0.8 (3) |
C4—C5—C6—C7 | 177.80 (17) | C9—C10—C11—C12 | 178.94 (17) |
Cl1—C5—C6—C7 | −5.7 (2) | C10—C11—C12—C13 | −0.7 (3) |
C2—C1—C6—C5 | 3.3 (3) | C11—C12—C13—C14 | 1.8 (3) |
C2—C1—C6—C7 | −177.43 (17) | C11—C12—C13—Cl2 | −176.63 (15) |
C8—N1—C7—O1 | −8.5 (3) | C12—C13—C14—C15 | −1.4 (3) |
C8—N1—C7—C6 | 172.51 (16) | Cl2—C13—C14—C15 | 177.03 (15) |
C5—C6—C7—O1 | 108.9 (2) | C13—C14—C15—C10 | −0.1 (3) |
C1—C6—C7—O1 | −70.3 (2) | C11—C10—C15—C14 | 1.2 (3) |
C5—C6—C7—N1 | −72.0 (2) | C9—C10—C15—C14 | −178.53 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.92 | 2.613 (2) | 136 |
N3—H3A···S1 | 0.86 | 2.71 | 2.9925 (17) | 101 |
N1—H1A···S1i | 0.86 | 2.52 | 3.3649 (17) | 170 |
C11—H11A···O2ii | 0.93 | 2.42 | 3.329 (2) | 166 |
C12—H12A···O1ii | 0.93 | 2.58 | 3.426 (2) | 151 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+2, −z. |
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