2-Chloro-N-[N-(4-chloro­benzoyl)­hydrazinocarbo­thio­yl]­benz­amide

Ali, H.; Yusof, M.S.; Khamis, N.A.; Mardi, A.S.; Yamin, B.M.

doi:10.1107/S1600536804020525

2-Chloro-N-[N-(4-chlorobenzoyl)hydrazinocarbothioyl]benzamide

H. Ali, M. S. Yusof, N. A. Khamis, A. S. Mardi and B. M. Yamin

The title compound, C₁₅H₁₁Cl₂N₃O₂S, 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020525/rn6021sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020525/rn6021Isup2.hkl Contains datablock I

CCDC reference: 251763

checkCIF report

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

Computing details top

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
M_r = 368.24	F(000) = 376
Triclinic, P1	D_x = 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	R_int = 0.015
Detector resolution: 83.66 pixels mm^-1	θ_max = 27.0°, θ_min = 1.9°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
T_min = 0.783, T_max = 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(F_o²) + (0.0581P)² + 0.2898P] where P = (F_o² + 2F_c²)/3
3549 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

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

	x	y	z	U_iso*/U_eq
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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2-Chloro-N-[N-(4-chloro­benzoyl)­hydrazinocarbo­thio­yl]­benz­amide

Supporting information

Key indicators

checkCIF/PLATON results

2-Chloro-N-[N-(4-chlorobenzoyl)hydrazinocarbothioyl]benzamide