Literature DB >> 22058758

N'-[(E)-2-Chloro-benzyl-idene]-2-[(1,3,4-thia-diazol-2-yl)sulfan-yl]acetohydrazide.

S Mohan, S Ananthan, P Ramesh, D Saravanan, M N Ponnuswamy.

Abstract

In the title compound, C(11)H(9)ClN(4)OS(2), the thia-diazole and chloro-phenyl rings are oriented at an angle of 43.1 (1)°. The sum of the bond angles around the amide N atom (359.8°) of the acetohydrazide group is in accordance with a model of sp(2) hybridization. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(8) loops. Weak C-H⋯π inter-actions also occur.

Entities: Chemical Disease Gene Species

Year: 2011 PMID： 22058758 PMCID： PMC3201361 DOI： 10.1107/S1600536811035549

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For related literature on the biological activities of 1,3,4-thiadiazole derivatives, see: Alireza et al. (2005 ▶); Matysiak & Opolski (2006 ▶); Wang et al. (1999 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H9ClN4OS2 M = 312.79 Triclinic, a = 7.551 (5) Å b = 8.743 (3) Å c = 11.269 (5) Å α = 69.295 (5)° β = 87.493 (4)° γ = 78.892 (5)° V = 682.6 (6) Å3 Z = 2 Mo Kα radiation μ = 0.58 mm−1 T = 293 K 0.20 × 0.17 × 0.16 mm

Data collection

Bruker SMART APEXII area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.890, T max = 0.911 12836 measured reflections 3446 independent reflections 2858 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.121 S = 1.05 3446 reflections 176 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.81 e Å−3 Δρmin = −0.70 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035549/bt5593sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035549/bt5593Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811035549/bt5593Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₁H₉ClN₄OS₂	Z = 2
M_r = 312.79	F(000) = 320
Triclinic, P1	D_x = 1.522 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.551 (5) Å	Cell parameters from 1536 reflections
b = 8.743 (3) Å	θ = 1.9–28.6°
c = 11.269 (5) Å	µ = 0.58 mm⁻¹
α = 69.295 (5)°	T = 293 K
β = 87.493 (4)°	Block, colorless
γ = 78.892 (5)°	0.20 × 0.17 × 0.16 mm
V = 682.6 (6) Å³

Bruker SMART APEXII area-detector diffractometer	3446 independent reflections
Radiation source: fine-focus sealed tube	2858 reflections with I > 2σ(I)
graphite	R_int = 0.026
ω and φ scans	θ_max = 28.6°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
T_min = 0.890, T_max = 0.911	k = −11→11
12836 measured reflections	l = −15→15

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0552P)² + 0.298P] where P = (F_o² + 2F_c²)/3
3446 reflections	(Δ/σ)_max < 0.001
176 parameters	Δρ_max = 0.81 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
S1	0.25535 (9)	0.03479 (8)	0.74213 (5)	0.06663 (19)
S2	0.56742 (7)	0.20903 (7)	0.65247 (4)	0.05462 (16)
Cl1	0.84070 (13)	0.88994 (8)	−0.05412 (6)	0.0894 (3)
O1	0.8486 (2)	0.3817 (2)	0.59757 (12)	0.0554 (3)
C1	0.1207 (3)	0.0256 (3)	0.6276 (2)	0.0626 (5)
H1	0.0209	−0.0258	0.6469	0.075*
N2	0.1673 (3)	0.0946 (3)	0.51348 (18)	0.0629 (5)
N3	0.3200 (3)	0.1628 (2)	0.50782 (16)	0.0562 (4)
C4	0.3807 (3)	0.1407 (2)	0.61968 (17)	0.0463 (4)
C5	0.6334 (3)	0.3041 (2)	0.49114 (16)	0.0471 (4)
H5A	0.6700	0.2203	0.4524	0.057*
H5B	0.5333	0.3857	0.4414	0.057*
C6	0.7884 (2)	0.3867 (2)	0.49625 (16)	0.0438 (4)
N7	0.8544 (2)	0.4699 (2)	0.38490 (14)	0.0489 (4)
H7	0.950 (3)	0.519 (3)	0.386 (2)	0.065 (7)*
N8	0.7873 (2)	0.4676 (2)	0.27372 (13)	0.0460 (3)
C9	0.8396 (2)	0.5689 (2)	0.17253 (16)	0.0449 (4)
H9	0.9113	0.6420	0.1773	0.054*
C10	0.7866 (2)	0.5701 (2)	0.04874 (16)	0.0454 (4)
C11	0.7840 (3)	0.7090 (3)	−0.06154 (18)	0.0556 (5)
C12	0.7388 (3)	0.7078 (3)	−0.17847 (19)	0.0672 (6)
H12	0.7370	0.8021	−0.2507	0.081*
C13	0.6966 (3)	0.5678 (4)	−0.1873 (2)	0.0729 (7)
H13	0.6667	0.5665	−0.2661	0.087*
C14	0.6980 (3)	0.4283 (4)	−0.0810 (2)	0.0694 (6)
H14	0.6692	0.3330	−0.0880	0.083*
C15	0.7423 (3)	0.4294 (3)	0.0368 (2)	0.0562 (5)
H15	0.7422	0.3348	0.1085	0.067*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0858 (4)	0.0739 (4)	0.0431 (3)	−0.0386 (3)	0.0118 (3)	−0.0131 (2)
S2	0.0671 (3)	0.0632 (3)	0.0327 (2)	−0.0252 (2)	−0.00281 (19)	−0.0087 (2)
Cl1	0.1404 (7)	0.0620 (4)	0.0558 (3)	−0.0234 (4)	−0.0051 (4)	−0.0055 (3)
O1	0.0617 (8)	0.0749 (9)	0.0336 (6)	−0.0256 (7)	−0.0014 (5)	−0.0173 (6)
C1	0.0675 (13)	0.0632 (13)	0.0646 (13)	−0.0273 (11)	0.0083 (10)	−0.0247 (10)
N2	0.0700 (11)	0.0703 (12)	0.0560 (10)	−0.0295 (9)	0.0011 (8)	−0.0228 (9)
N3	0.0681 (11)	0.0625 (10)	0.0417 (8)	−0.0259 (8)	0.0007 (7)	−0.0155 (7)
C4	0.0587 (11)	0.0410 (8)	0.0378 (8)	−0.0138 (8)	0.0045 (7)	−0.0102 (7)
C5	0.0586 (11)	0.0522 (10)	0.0329 (8)	−0.0178 (8)	0.0016 (7)	−0.0140 (7)
C6	0.0475 (9)	0.0489 (9)	0.0345 (8)	−0.0097 (7)	−0.0018 (7)	−0.0134 (7)
N7	0.0493 (9)	0.0647 (10)	0.0330 (7)	−0.0199 (8)	−0.0038 (6)	−0.0125 (7)
N8	0.0448 (8)	0.0608 (9)	0.0320 (7)	−0.0129 (7)	−0.0030 (6)	−0.0138 (6)
C9	0.0429 (9)	0.0537 (10)	0.0365 (8)	−0.0108 (7)	−0.0017 (7)	−0.0126 (7)
C10	0.0395 (8)	0.0597 (11)	0.0341 (8)	−0.0061 (7)	0.0009 (6)	−0.0148 (7)
C11	0.0578 (11)	0.0646 (12)	0.0369 (9)	−0.0040 (9)	−0.0001 (8)	−0.0127 (8)
C12	0.0677 (14)	0.0887 (17)	0.0342 (9)	−0.0003 (12)	−0.0031 (9)	−0.0154 (10)
C13	0.0602 (13)	0.118 (2)	0.0442 (11)	−0.0046 (13)	−0.0054 (9)	−0.0385 (13)
C14	0.0605 (13)	0.0982 (18)	0.0666 (14)	−0.0197 (12)	0.0004 (11)	−0.0470 (14)
C15	0.0530 (11)	0.0702 (13)	0.0489 (10)	−0.0155 (9)	0.0012 (8)	−0.0230 (9)

S1—C1	1.711 (3)	N7—H7	0.91 (3)
S1—C4	1.725 (2)	N8—C9	1.273 (2)
S2—C4	1.734 (2)	C9—C10	1.464 (2)
S2—C5	1.8044 (19)	C9—H9	0.9300
Cl1—C11	1.747 (3)	C10—C15	1.387 (3)
O1—C6	1.231 (2)	C10—C11	1.394 (3)
C1—N2	1.278 (3)	C11—C12	1.380 (3)
C1—H1	0.9300	C12—C13	1.360 (4)
N2—N3	1.386 (3)	C12—H12	0.9300
N3—C4	1.296 (2)	C13—C14	1.373 (4)
C5—C6	1.502 (3)	C13—H13	0.9300
C5—H5A	0.9700	C14—C15	1.387 (3)
C5—H5B	0.9700	C14—H14	0.9300
C6—N7	1.338 (2)	C15—H15	0.9300
N7—N8	1.380 (2)

C1—S1—C4	86.64 (11)	C9—N8—N7	115.02 (16)
C4—S2—C5	97.92 (9)	N8—C9—C10	119.93 (17)
N2—C1—S1	115.12 (18)	N8—C9—H9	120.0
N2—C1—H1	122.4	C10—C9—H9	120.0
S1—C1—H1	122.4	C15—C10—C11	117.46 (18)
C1—N2—N3	112.27 (18)	C15—C10—C9	120.55 (17)
C4—N3—N2	112.06 (17)	C11—C10—C9	121.96 (19)
N3—C4—S1	113.92 (16)	C12—C11—C10	121.7 (2)
N3—C4—S2	126.04 (15)	C12—C11—Cl1	118.25 (18)
S1—C4—S2	120.04 (11)	C10—C11—Cl1	120.05 (16)
C6—C5—S2	107.09 (12)	C13—C12—C11	119.5 (2)
C6—C5—H5A	110.3	C13—C12—H12	120.2
S2—C5—H5A	110.3	C11—C12—H12	120.2
C6—C5—H5B	110.3	C12—C13—C14	120.6 (2)
S2—C5—H5B	110.3	C12—C13—H13	119.7
H5A—C5—H5B	108.6	C14—C13—H13	119.7
O1—C6—N7	121.70 (17)	C13—C14—C15	120.0 (2)
O1—C6—C5	121.66 (16)	C13—C14—H14	120.0
N7—C6—C5	116.62 (15)	C15—C14—H14	120.0
C6—N7—N8	119.89 (16)	C10—C15—C14	120.7 (2)
C6—N7—H7	118.1 (16)	C10—C15—H15	119.6
N8—N7—H7	121.8 (16)	C14—C15—H15	119.6

C4—S1—C1—N2	−0.2 (2)	N7—N8—C9—C10	176.09 (16)
S1—C1—N2—N3	0.1 (3)	N8—C9—C10—C15	−24.7 (3)
C1—N2—N3—C4	0.1 (3)	N8—C9—C10—C11	157.42 (19)
N2—N3—C4—S1	−0.3 (2)	C15—C10—C11—C12	0.2 (3)
N2—N3—C4—S2	−179.38 (15)	C9—C10—C11—C12	178.18 (19)
C1—S1—C4—N3	0.26 (17)	C15—C10—C11—Cl1	−179.30 (15)
C1—S1—C4—S2	179.43 (14)	C9—C10—C11—Cl1	−1.3 (3)
C5—S2—C4—N3	−1.1 (2)	C10—C11—C12—C13	−0.5 (3)
C5—S2—C4—S1	179.81 (12)	Cl1—C11—C12—C13	179.03 (18)
C4—S2—C5—C6	175.22 (13)	C11—C12—C13—C14	0.3 (4)
S2—C5—C6—O1	0.3 (2)	C12—C13—C14—C15	0.1 (4)
S2—C5—C6—N7	−177.98 (14)	C11—C10—C15—C14	0.2 (3)
O1—C6—N7—N8	177.73 (17)	C9—C10—C15—C14	−177.78 (19)
C5—C6—N7—N8	−4.0 (3)	C13—C14—C15—C10	−0.4 (3)
C6—N7—N8—C9	170.33 (17)

Cg1 is the centroid of the S1/C1/N2/N3/C4 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cl1	0.93	2.73	3.056 (2)	102.
N7—H7···O1ⁱ	0.91 (3)	1.93 (3)	2.845 (3)	175 (2)
C5—H5A···Cg1ⁱⁱ	0.97	2.95	3.896 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1/C1/N2/N3/C4 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O1ⁱ	0.91 (3)	1.93 (3)	2.845 (3)	175 (2)
C5—H5A⋯Cg1ⁱⁱ	0.97	2.95	3.896(3)	165

Symmetry codes: (i) ; (ii) .

3 in total

N'-[(E)-2-Chloro-benzyl-idene]-2-[(1,3,4-thia-diazol-2-yl)sulfan-yl]acetohydrazide.

Related literature

Experimental

Crystal data

Data collection

Refinement

1. A short history of SHELX.

2. Synthesis and antiproliferative activity of N-substituted 2-amino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazoles.

3. Structure validation in chemical crystallography.