Crystal structure of 2-[(E)-2-(2-chloro­benzyl­idene)hydrazin-1-yl]-4-phenyl-1,3-thia­zole

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Hassan, A.A.; Albayati, M.R.

doi:10.1107/S1600536814016298

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o907-o908

doi:10.1107/S1600536814016298

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Crystal structure of 2-[(E)-2-(2-chlorobenzylidene)hydrazin-1-yl]-4-phenyl-1,3-thiazole

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Alaa A. Hassan ^c and Mustafa R. Albayati ^e ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Mini University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 11 July 2014; accepted 14 July 2014; online 1 August 2014)

The asymmetric unit of the title compound, C₁₆H₁₂ClN₃S, contains two independent molecules whose conformations differ primarily in the orientations of the phenyl and chlorobenzene rings with respect to the thiazole ring. In the first molecule, the dihedral angles are 3.0 (1) and 9.2 (1)°, respectively, for the phenyl ring and the chlorobenzene ring, while in the second molecule, the corresponding angles are 18.6 (1) and 23.4 (1)°. In the crystal, the two independent molecules are associated via complementary N—H⋯N hydrogen bonds into a dimer. These dimers are associated through weak C—H⋯Cl and C—H⋯S interactions into supramolecular chains propagating along the a-axis direction.

Keywords: crystal structure; 1,3-thiazole; hydrogen bonding; hydrogen-bonded dimers.

CCDC reference: 1013753

1. Related literature

For pharmaceutical properties of thiazole derivatives, see: Siddiqui et al. (2011 , 2009 ); Bakris et al. (2004 ); Little et al. (2005 ). For the synthesis of the title compound, see: Mohamed et al. (2013 ).

2. Experimental

2.1. Crystal data

C₁₆H₁₂ClN₃S
M_r = 313.80
Orthorhombic, P b c a
a = 16.981 (4) Å
b = 8.1081 (17) Å
c = 41.660 (9) Å
V = 5736 (2) Å³
Z = 16
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 150 K
0.22 × 0.22 × 0.05 mm

2.2. Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.80, T_max = 0.98
99305 measured reflections
7415 independent reflections
5577 reflections with I > 2σ(I)
R_int = 0.086

2.3. Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.109
S = 1.04
7415 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N6	0.91	2.02	2.901 (2)	163
N5—H5A⋯N3	0.91	2.05	2.946 (2)	166
C9—H9⋯S1ⁱ	0.95	2.97	3.696 (2)	134
C25—H25⋯Cl1ⁱⁱ	0.95	2.92	3.720 (2)	143
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2013); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1013753

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814016298/xu5803sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814016298/xu5803Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814016298/xu5803Isup3.cml

checkCIF report

Comment top

Thiazole containing compounds have been reported to possess large number of biological properties (Siddiqui et al., 2011; Siddiqui et al., 2009). Sulfathiazol (antimicrobial drug), Ritonavir (antiretroviral drug), Abafungin (antifungal drug), Bleomycine and Tiazofurin (antineoplastic drug) are common drugs with thiazole-based structures. Alagebrium (formerly known as ALT-711) is also a thiazolium salt which was the first drug used for breaking the protein crosslinks caused by advanced glycation endproducts (AGEs). Through this effect Alagebrium is designed to reverse the stiffening of blood vessel walls that contributes to hypertension and cardiovascular disease (Bakris et al., 2004; Little et al., 2005). İn this context and as part of our study in synthesis of potential bioactive heterocyclic molecules, we report the synthesis and crystal structure of the title compound.

There are two independent molecules of the title compound in the asymmetric unit whose conformations differ primarily in the orientations of the phenyl rings with respect to the thiazole ring. For molecule 1, the dihedral angles are 3.0 (1) and 9.2 (1)°, respectively, for rings C1–C6 and C11–C16 while for molecule 2 the corresponding angles are 18.6 (1) and 23.4 (1)°.

In the crystal structure, the two independent molecules are associated via complementary N—H···N hydrogen bonds (Fig. 1 and Table 1). These pairs are associated into chains running along the a axis through weak C—H···Cl interactions (Table 1) and weak C—H···S interactions (Table 1).

Related literature top

For pharmaceutical properties of thiazole derivatives, see: Siddiqui et al. (2011, 2009); Bakris et al. (2004); Little et al. (2005). For the synthesis of the title compound, see: Mohamed et al. (2013).

Experimental top

The title compound has been prepared according to our reported method (Mohamed et al., 2013). Colourless crystals suitable for X-ray diffraction have been obtained by crystallization of the crude product (I) from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Bruker, 2013); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Bruker, 2013).

Figures top

Fig. 1. The asymmetric unit with the complementary N—H···N hydrogen bonds shown as dotted lines. Ellipsoids are drawn at the 50% probability level.

2-[(E)-2-[(2-chlorophenyl)methylidene]hydrazin-1-yl]-4-phenyl-1,3-thiazole top

Crystal data top

C₁₆H₁₂ClN₃S	D_x = 1.454 Mg m⁻³
M_r = 313.80	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9986 reflections
a = 16.981 (4) Å	θ = 2.6–28.7°
b = 8.1081 (17) Å	µ = 0.41 mm⁻¹
c = 41.660 (9) Å	T = 150 K
V = 5736 (2) Å³	Plate, colourless
Z = 16	0.22 × 0.22 × 0.05 mm
F(000) = 2592

Data collection top

Bruker SMART APEX CCD diffractometer	7415 independent reflections
Radiation source: fine-focus sealed tube	5577 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
Detector resolution: 8.3660 pixels mm^-1	θ_max = 28.8°, θ_min = 2.0°
ϕ and ω scans	h = −22→22
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −10→10
T_min = 0.80, T_max = 0.98	l = −55→56
99305 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0371P)² + 4.8434P] where P = (F_o² + 2F_c²)/3
7415 reflections	(Δ/σ)_max = 0.001
379 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₆H₁₂ClN₃S	V = 5736 (2) Å³
M_r = 313.80	Z = 16
Orthorhombic, Pbca	Mo Kα radiation
a = 16.981 (4) Å	µ = 0.41 mm⁻¹
b = 8.1081 (17) Å	T = 150 K
c = 41.660 (9) Å	0.22 × 0.22 × 0.05 mm

Data collection top

Bruker SMART APEX CCD diffractometer	7415 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	5577 reflections with I > 2σ(I)
T_min = 0.80, T_max = 0.98	R_int = 0.086
99305 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.04	Δρ_max = 0.42 e Å⁻³
7415 reflections	Δρ_min = −0.33 e Å⁻³
379 parameters

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, collected at ϕ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in ϕ, collected at ω = -30.00 and 210.00°. The scan time was 15 sec/frame.

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 Å) while those attached to nitrogen were placed in locations derived from a difference map and, following initial independent refinement to verify their presence, their coordinates were adjusted to give N—H = 0.91 Å. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

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

	x	y	z	U_iso*/U_eq
Cl1	0.42874 (3)	0.85456 (8)	0.45306 (2)	0.04262 (15)
S1	0.67429 (3)	0.24168 (6)	0.37657 (2)	0.02704 (12)
N1	0.57267 (10)	0.4806 (2)	0.40738 (4)	0.0248 (3)
N2	0.53242 (10)	0.3466 (2)	0.39636 (4)	0.0266 (4)
H2A	0.4789	0.3475	0.3972	0.032*
N3	0.54083 (9)	0.0943 (2)	0.36976 (4)	0.0235 (3)
C1	0.52954 (12)	0.8719 (3)	0.44674 (5)	0.0266 (4)
C2	0.56720 (14)	1.0112 (3)	0.45834 (5)	0.0325 (5)
H2	0.5382	1.0943	0.4692	0.039*
C3	0.64723 (14)	1.0279 (3)	0.45392 (5)	0.0354 (5)
H3	0.6737	1.1225	0.4620	0.042*
C4	0.68913 (13)	0.9078 (3)	0.43785 (5)	0.0326 (5)
H4	0.7442	0.9205	0.4346	0.039*
C5	0.65150 (12)	0.7700 (3)	0.42652 (5)	0.0268 (4)
H5	0.6811	0.6881	0.4156	0.032*
C6	0.57031 (11)	0.7473 (2)	0.43076 (4)	0.0229 (4)
C7	0.53147 (11)	0.5992 (2)	0.41884 (5)	0.0244 (4)
H7	0.4757	0.5905	0.4196	0.029*
C8	0.57334 (11)	0.2272 (2)	0.38144 (4)	0.0221 (4)
C9	0.67232 (11)	0.0512 (2)	0.35830 (5)	0.0263 (4)
H9	0.7175	−0.0043	0.3503	0.032*
C10	0.59793 (11)	−0.0091 (2)	0.35689 (4)	0.0226 (4)
C11	0.57380 (11)	−0.1716 (2)	0.34490 (5)	0.0239 (4)
C12	0.62690 (12)	−0.2731 (3)	0.32880 (5)	0.0295 (4)
H12	0.6792	−0.2358	0.3252	0.035*
C13	0.60464 (13)	−0.4266 (3)	0.31801 (5)	0.0339 (5)
H13	0.6417	−0.4947	0.3073	0.041*
C14	0.52845 (14)	−0.4821 (3)	0.32276 (5)	0.0336 (5)
H14	0.5131	−0.5877	0.3151	0.040*
C15	0.47497 (13)	−0.3835 (3)	0.33864 (5)	0.0321 (5)
H15	0.4225	−0.4210	0.3418	0.039*
C16	0.49763 (12)	−0.2292 (3)	0.34997 (5)	0.0276 (4)
H16	0.4608	−0.1627	0.3613	0.033*
Cl2	0.51373 (3)	−0.18369 (8)	0.25484 (2)	0.03684 (14)
S2	0.23921 (3)	0.26852 (7)	0.35529 (2)	0.03059 (13)
N4	0.35122 (10)	0.0848 (2)	0.31580 (4)	0.0254 (4)
N5	0.38660 (10)	0.1670 (2)	0.34063 (4)	0.0279 (4)
H5A	0.4365	0.1386	0.3464	0.033*
N6	0.36410 (9)	0.2951 (2)	0.39001 (4)	0.0242 (3)
C17	0.41198 (12)	−0.1953 (3)	0.25184 (5)	0.0255 (4)
C18	0.38063 (13)	−0.2967 (3)	0.22837 (5)	0.0301 (4)
H18	0.4145	−0.3575	0.2146	0.036*
C19	0.30033 (13)	−0.3091 (3)	0.22512 (5)	0.0317 (5)
H19	0.2786	−0.3785	0.2090	0.038*
C20	0.25097 (13)	−0.2208 (3)	0.24522 (5)	0.0327 (5)
H20	0.1955	−0.2294	0.2429	0.039*
C21	0.28249 (12)	−0.1202 (3)	0.26869 (5)	0.0287 (4)
H21	0.2482	−0.0608	0.2825	0.034*
C22	0.36410 (12)	−0.1042 (2)	0.27246 (5)	0.0245 (4)
C23	0.39660 (12)	−0.0014 (3)	0.29797 (5)	0.0258 (4)
H23	0.4519	0.0014	0.3014	0.031*
C24	0.33820 (11)	0.2402 (2)	0.36249 (5)	0.0232 (4)
C25	0.23213 (12)	0.3603 (3)	0.39246 (5)	0.0299 (5)
H25	0.1847	0.4030	0.4013	0.036*
C26	0.30284 (11)	0.3639 (2)	0.40748 (5)	0.0236 (4)
C27	0.31902 (11)	0.4215 (2)	0.44032 (5)	0.0233 (4)
C28	0.26964 (12)	0.5346 (3)	0.45548 (5)	0.0281 (4)
H28	0.2254	0.5774	0.4443	0.034*
C29	0.28430 (13)	0.5849 (3)	0.48644 (5)	0.0325 (5)
H29	0.2504	0.6627	0.4964	0.039*
C30	0.34853 (14)	0.5223 (3)	0.50318 (5)	0.0353 (5)
H30	0.3586	0.5568	0.5246	0.042*
C31	0.39759 (13)	0.4097 (3)	0.48843 (5)	0.0334 (5)
H31	0.4415	0.3667	0.4998	0.040*
C32	0.38344 (12)	0.3590 (3)	0.45732 (5)	0.0269 (4)
H32	0.4176	0.2813	0.4474	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0279 (3)	0.0448 (3)	0.0552 (4)	0.0053 (2)	0.0023 (2)	−0.0128 (3)
S1	0.0191 (2)	0.0260 (2)	0.0360 (3)	−0.00266 (19)	−0.00276 (19)	0.0003 (2)
N1	0.0269 (8)	0.0228 (8)	0.0246 (8)	−0.0049 (7)	−0.0031 (7)	−0.0022 (7)
N2	0.0205 (8)	0.0251 (9)	0.0341 (9)	−0.0045 (7)	0.0005 (7)	−0.0074 (7)
N3	0.0202 (7)	0.0236 (8)	0.0266 (8)	−0.0010 (6)	0.0007 (6)	−0.0024 (7)
C1	0.0280 (10)	0.0266 (10)	0.0253 (10)	0.0033 (8)	−0.0039 (8)	−0.0001 (8)
C2	0.0422 (12)	0.0242 (10)	0.0311 (11)	0.0037 (9)	−0.0050 (9)	−0.0056 (9)
C3	0.0445 (13)	0.0260 (11)	0.0356 (12)	−0.0073 (10)	−0.0116 (10)	−0.0035 (9)
C4	0.0326 (11)	0.0320 (11)	0.0333 (11)	−0.0066 (9)	−0.0033 (9)	0.0002 (9)
C5	0.0284 (10)	0.0275 (10)	0.0246 (10)	−0.0028 (8)	0.0002 (8)	−0.0012 (8)
C6	0.0272 (9)	0.0230 (9)	0.0184 (9)	−0.0020 (8)	−0.0031 (7)	0.0003 (7)
C7	0.0237 (9)	0.0258 (10)	0.0236 (9)	−0.0026 (8)	−0.0019 (7)	−0.0011 (8)
C8	0.0195 (8)	0.0245 (9)	0.0224 (9)	−0.0010 (7)	−0.0012 (7)	0.0006 (7)
C9	0.0227 (9)	0.0267 (10)	0.0295 (10)	0.0019 (8)	0.0008 (8)	0.0025 (8)
C10	0.0232 (9)	0.0243 (10)	0.0202 (9)	0.0030 (7)	−0.0015 (7)	0.0023 (7)
C11	0.0268 (9)	0.0233 (10)	0.0214 (9)	0.0014 (8)	−0.0041 (7)	0.0015 (7)
C12	0.0293 (10)	0.0300 (11)	0.0292 (10)	0.0032 (9)	−0.0006 (8)	−0.0032 (9)
C13	0.0391 (12)	0.0302 (11)	0.0325 (12)	0.0065 (9)	0.0008 (9)	−0.0042 (9)
C14	0.0454 (13)	0.0241 (10)	0.0313 (11)	−0.0014 (9)	−0.0036 (10)	−0.0025 (9)
C15	0.0342 (11)	0.0287 (11)	0.0334 (11)	−0.0042 (9)	−0.0025 (9)	0.0030 (9)
C16	0.0300 (10)	0.0249 (10)	0.0278 (10)	0.0002 (8)	−0.0001 (8)	−0.0002 (8)
Cl2	0.0278 (3)	0.0471 (3)	0.0356 (3)	0.0053 (2)	−0.0013 (2)	−0.0076 (2)
S2	0.0236 (2)	0.0383 (3)	0.0298 (3)	0.0043 (2)	−0.00573 (19)	−0.0034 (2)
N4	0.0273 (8)	0.0264 (9)	0.0226 (8)	−0.0035 (7)	−0.0023 (6)	−0.0020 (7)
N5	0.0219 (8)	0.0343 (10)	0.0274 (9)	0.0002 (7)	−0.0024 (7)	−0.0091 (7)
N6	0.0212 (8)	0.0261 (9)	0.0254 (8)	−0.0010 (7)	0.0002 (6)	−0.0030 (7)
C17	0.0278 (10)	0.0262 (10)	0.0227 (9)	0.0019 (8)	−0.0022 (7)	0.0030 (8)
C18	0.0400 (12)	0.0246 (10)	0.0257 (10)	0.0031 (9)	−0.0001 (9)	−0.0003 (8)
C19	0.0420 (12)	0.0261 (10)	0.0270 (11)	−0.0054 (9)	−0.0074 (9)	−0.0020 (9)
C20	0.0304 (10)	0.0339 (11)	0.0337 (11)	−0.0046 (9)	−0.0068 (9)	0.0008 (9)
C21	0.0297 (10)	0.0290 (11)	0.0275 (11)	0.0003 (9)	−0.0007 (8)	0.0000 (9)
C22	0.0295 (10)	0.0228 (10)	0.0211 (9)	−0.0003 (8)	−0.0027 (8)	0.0024 (8)
C23	0.0253 (9)	0.0281 (10)	0.0238 (10)	−0.0016 (8)	−0.0012 (7)	0.0007 (8)
C24	0.0204 (9)	0.0232 (9)	0.0259 (9)	−0.0020 (7)	−0.0010 (7)	−0.0002 (8)
C25	0.0241 (10)	0.0354 (12)	0.0302 (11)	0.0075 (9)	−0.0012 (8)	−0.0008 (9)
C26	0.0233 (9)	0.0203 (9)	0.0272 (10)	0.0006 (7)	0.0012 (7)	0.0013 (8)
C27	0.0241 (9)	0.0224 (9)	0.0234 (9)	−0.0015 (8)	0.0024 (7)	0.0014 (8)
C28	0.0284 (10)	0.0263 (10)	0.0296 (11)	0.0010 (8)	0.0011 (8)	0.0013 (9)
C29	0.0386 (12)	0.0287 (11)	0.0304 (11)	0.0028 (9)	0.0056 (9)	−0.0021 (9)
C30	0.0463 (13)	0.0361 (12)	0.0235 (10)	−0.0012 (10)	0.0006 (9)	−0.0017 (9)
C31	0.0348 (11)	0.0369 (12)	0.0287 (11)	0.0022 (9)	−0.0025 (9)	0.0020 (9)
C32	0.0256 (9)	0.0283 (10)	0.0269 (10)	0.0029 (8)	0.0014 (8)	−0.0002 (8)

Geometric parameters (Å, º) top

Cl1—C1	1.737 (2)	Cl2—C17	1.735 (2)
S1—C9	1.722 (2)	S2—C25	1.722 (2)
S1—C8	1.7301 (19)	S2—C24	1.723 (2)
N1—C7	1.282 (3)	N4—C23	1.278 (3)
N1—N2	1.363 (2)	N4—N5	1.370 (2)
N2—C8	1.344 (2)	N5—C24	1.363 (2)
N2—H2A	0.9098	N5—H5A	0.9100
N3—C8	1.305 (2)	N6—C24	1.306 (2)
N3—C10	1.389 (2)	N6—C26	1.387 (2)
C1—C2	1.385 (3)	C17—C18	1.384 (3)
C1—C6	1.394 (3)	C17—C22	1.395 (3)
C2—C3	1.378 (3)	C18—C19	1.374 (3)
C2—H2	0.9500	C18—H18	0.9500
C3—C4	1.380 (3)	C19—C20	1.384 (3)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.371 (3)	C20—C21	1.382 (3)
C4—H4	0.9500	C20—H20	0.9500
C5—C6	1.402 (3)	C21—C22	1.401 (3)
C5—H5	0.9500	C21—H21	0.9500
C6—C7	1.458 (3)	C22—C23	1.459 (3)
C7—H7	0.9500	C23—H23	0.9500
C9—C10	1.356 (3)	C25—C26	1.354 (3)
C9—H9	0.9500	C25—H25	0.9500
C10—C11	1.468 (3)	C26—C27	1.472 (3)
C11—C16	1.391 (3)	C27—C28	1.394 (3)
C11—C12	1.393 (3)	C27—C32	1.398 (3)
C12—C13	1.376 (3)	C28—C29	1.375 (3)
C12—H12	0.9500	C28—H28	0.9500
C13—C14	1.384 (3)	C29—C30	1.390 (3)
C13—H13	0.9500	C29—H29	0.9500
C14—C15	1.379 (3)	C30—C31	1.380 (3)
C14—H14	0.9500	C30—H30	0.9500
C15—C16	1.391 (3)	C31—C32	1.381 (3)
C15—H15	0.9500	C31—H31	0.9500
C16—H16	0.9500	C32—H32	0.9500

C9—S1—C8	88.38 (9)	C25—S2—C24	88.24 (9)
C7—N1—N2	116.74 (16)	C23—N4—N5	116.15 (17)
C8—N2—N1	118.06 (16)	C24—N5—N4	116.89 (16)
C8—N2—H2A	122.8	C24—N5—H5A	119.7
N1—N2—H2A	118.7	N4—N5—H5A	118.9
C8—N3—C10	110.30 (16)	C24—N6—C26	110.19 (16)
C2—C1—C6	121.89 (19)	C18—C17—C22	121.71 (19)
C2—C1—Cl1	117.90 (16)	C18—C17—Cl2	117.79 (16)
C6—C1—Cl1	120.21 (16)	C22—C17—Cl2	120.50 (15)
C3—C2—C1	119.3 (2)	C19—C18—C17	119.6 (2)
C3—C2—H2	120.4	C19—C18—H18	120.2
C1—C2—H2	120.4	C17—C18—H18	120.2
C2—C3—C4	120.3 (2)	C18—C19—C20	120.2 (2)
C2—C3—H3	119.9	C18—C19—H19	119.9
C4—C3—H3	119.9	C20—C19—H19	119.9
C5—C4—C3	120.1 (2)	C21—C20—C19	119.9 (2)
C5—C4—H4	119.9	C21—C20—H20	120.0
C3—C4—H4	119.9	C19—C20—H20	120.0
C4—C5—C6	121.5 (2)	C20—C21—C22	121.2 (2)
C4—C5—H5	119.3	C20—C21—H21	119.4
C6—C5—H5	119.3	C22—C21—H21	119.4
C1—C6—C5	116.98 (18)	C17—C22—C21	117.30 (18)
C1—C6—C7	122.36 (18)	C17—C22—C23	122.05 (18)
C5—C6—C7	120.66 (18)	C21—C22—C23	120.59 (18)
N1—C7—C6	119.91 (18)	N4—C23—C22	120.50 (18)
N1—C7—H7	120.0	N4—C23—H23	119.8
C6—C7—H7	120.0	C22—C23—H23	119.8
N3—C8—N2	123.26 (17)	N6—C24—N5	122.14 (17)
N3—C8—S1	115.56 (15)	N6—C24—S2	115.85 (15)
N2—C8—S1	121.18 (14)	N5—C24—S2	122.01 (14)
C10—C9—S1	111.14 (15)	C26—C25—S2	111.26 (15)
C10—C9—H9	124.4	C26—C25—H25	124.4
S1—C9—H9	124.4	S2—C25—H25	124.4
C9—C10—N3	114.57 (18)	C25—C26—N6	114.46 (18)
C9—C10—C11	126.78 (18)	C25—C26—C27	126.99 (18)
N3—C10—C11	118.58 (17)	N6—C26—C27	118.41 (17)
C16—C11—C12	118.49 (19)	C28—C27—C32	118.67 (19)
C16—C11—C10	120.61 (18)	C28—C27—C26	121.19 (18)
C12—C11—C10	120.88 (18)	C32—C27—C26	120.11 (18)
C13—C12—C11	120.9 (2)	C29—C28—C27	120.7 (2)
C13—C12—H12	119.6	C29—C28—H28	119.6
C11—C12—H12	119.6	C27—C28—H28	119.6
C12—C13—C14	120.3 (2)	C28—C29—C30	120.3 (2)
C12—C13—H13	119.9	C28—C29—H29	119.9
C14—C13—H13	119.9	C30—C29—H29	119.9
C15—C14—C13	119.7 (2)	C31—C30—C29	119.4 (2)
C15—C14—H14	120.1	C31—C30—H30	120.3
C13—C14—H14	120.1	C29—C30—H30	120.3
C14—C15—C16	120.1 (2)	C30—C31—C32	120.7 (2)
C14—C15—H15	119.9	C30—C31—H31	119.7
C16—C15—H15	119.9	C32—C31—H31	119.7
C11—C16—C15	120.5 (2)	C31—C32—C27	120.23 (19)
C11—C16—H16	119.8	C31—C32—H32	119.9
C15—C16—H16	119.8	C27—C32—H32	119.9

C7—N1—N2—C8	173.77 (18)	C23—N4—N5—C24	−170.95 (18)
C6—C1—C2—C3	0.2 (3)	C22—C17—C18—C19	−0.1 (3)
Cl1—C1—C2—C3	179.50 (17)	Cl2—C17—C18—C19	−179.82 (17)
C1—C2—C3—C4	0.6 (3)	C17—C18—C19—C20	−0.1 (3)
C2—C3—C4—C5	−0.8 (3)	C18—C19—C20—C21	−0.2 (3)
C3—C4—C5—C6	0.2 (3)	C19—C20—C21—C22	0.6 (3)
C2—C1—C6—C5	−0.8 (3)	C18—C17—C22—C21	0.5 (3)
Cl1—C1—C6—C5	179.94 (15)	Cl2—C17—C22—C21	−179.80 (15)
C2—C1—C6—C7	179.12 (19)	C18—C17—C22—C23	177.84 (19)
Cl1—C1—C6—C7	−0.1 (3)	Cl2—C17—C22—C23	−2.4 (3)
C4—C5—C6—C1	0.6 (3)	C20—C21—C22—C17	−0.7 (3)
C4—C5—C6—C7	−179.34 (19)	C20—C21—C22—C23	−178.12 (19)
N2—N1—C7—C6	−179.33 (17)	N5—N4—C23—C22	175.08 (17)
C1—C6—C7—N1	−172.59 (19)	C17—C22—C23—N4	177.70 (19)
C5—C6—C7—N1	7.3 (3)	C21—C22—C23—N4	−5.0 (3)
C10—N3—C8—N2	−177.70 (18)	C26—N6—C24—N5	179.78 (18)
C10—N3—C8—S1	2.3 (2)	C26—N6—C24—S2	0.6 (2)
N1—N2—C8—N3	−179.50 (18)	N4—N5—C24—N6	167.05 (18)
N1—N2—C8—S1	0.5 (3)	N4—N5—C24—S2	−13.8 (3)
C9—S1—C8—N3	−1.55 (16)	C25—S2—C24—N6	−0.41 (17)
C9—S1—C8—N2	178.42 (17)	C25—S2—C24—N5	−179.58 (18)
C8—S1—C9—C10	0.33 (16)	C24—S2—C25—C26	0.07 (17)
S1—C9—C10—N3	0.9 (2)	S2—C25—C26—N6	0.3 (2)
S1—C9—C10—C11	−175.89 (16)	S2—C25—C26—C27	−175.32 (16)
C8—N3—C10—C9	−2.0 (2)	C24—N6—C26—C25	−0.6 (3)
C8—N3—C10—C11	175.04 (17)	C24—N6—C26—C27	175.43 (17)
C9—C10—C11—C16	168.6 (2)	C25—C26—C27—C28	−24.5 (3)
N3—C10—C11—C16	−8.0 (3)	N6—C26—C27—C28	160.09 (18)
C9—C10—C11—C12	−10.1 (3)	C25—C26—C27—C32	153.4 (2)
N3—C10—C11—C12	173.30 (18)	N6—C26—C27—C32	−22.0 (3)
C16—C11—C12—C13	0.2 (3)	C32—C27—C28—C29	0.6 (3)
C10—C11—C12—C13	178.94 (19)	C26—C27—C28—C29	178.54 (19)
C11—C12—C13—C14	0.6 (3)	C27—C28—C29—C30	−0.5 (3)
C12—C13—C14—C15	−0.6 (3)	C28—C29—C30—C31	0.2 (3)
C13—C14—C15—C16	−0.3 (3)	C29—C30—C31—C32	0.0 (3)
C12—C11—C16—C15	−1.2 (3)	C30—C31—C32—C27	0.1 (3)
C10—C11—C16—C15	−179.87 (18)	C28—C27—C32—C31	−0.4 (3)
C14—C15—C16—C11	1.2 (3)	C26—C27—C32—C31	−178.36 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N6	0.91	2.02	2.901 (2)	163
N5—H5A···N3	0.91	2.05	2.946 (2)	166
C9—H9···S1ⁱ	0.95	2.97	3.696 (2)	134
C25—H25···Cl1ⁱⁱ	0.95	2.92	3.720 (2)	143

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) −x+1/2, y−1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N6	0.91	2.02	2.901 (2)	163
N5—H5A···N3	0.91	2.05	2.946 (2)	166
C9—H9···S1ⁱ	0.95	2.97	3.696 (2)	134
C25—H25···Cl1ⁱⁱ	0.95	2.92	3.720 (2)	143

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) −x+1/2, y−1/2, z.

Acknowledgements

JTM thanks Tulane University for the support of the Tulane Crystallography Laboratory.

References

Bakris, G. L., Bank, A. J., Kass, D. A., Neutel, J. M., Preston, R. A. & Oparil, S. (2004). Am. J. Hypertens. 17, 23S–30S. Web of Science CrossRef PubMed CAS Google Scholar
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Bruker (2013). APEX2, SHELXTL, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Little, W. C., Zile, M. R., Kitzman, D. W., Hundley, W. G., O'Brien, T. X. & Degroof, R. C. (2005). J. Card. Fail. 11, 191–195. Web of Science CrossRef PubMed CAS Google Scholar
Mohamed, S. K., Mague, J. T., Akkurt, M., Hassan, A. A. & Albayati, M. R. (2013). Acta Cryst. E69, o1324. CSD CrossRef IUCr Journals Google Scholar
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Siddiqui, N., Arshad, M. F., Ahsan, W. & Alam, M. S. (2009). IJPSDR, 1, 136–143. CAS Google Scholar
Siddiqui, N., Arya, S. K., Ahsan, W. & Azad, B. (2011). Int. J. Drug Dev. Res., 3, 55–67. CAS Google Scholar

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o907-o908

doi:10.1107/S1600536814016298

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 2-[(E)-2-(2-chloro­benzyl­­idene)hydrazin-1-yl]-4-phenyl-1,3-thia­zole

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 2-[(E)-2-(2-chlorobenzylidene)hydrazin-1-yl]-4-phenyl-1,3-thiazole