N′-(3,4-Dichloro­benzyl­idene)-5-methyl-1-(4-nitro­phen­yl)-1H-1,2,3-triazole-4-carbohydrazide

Fun, H.-K.; Arshad, S.; Nithinchandra; Kalluraya, B.; Vidyashree, J.H.S.

doi:10.1107/S1600536812023112

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1902

doi:10.1107/S1600536812023112

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N′-(3,4-Dichlorobenzylidene)-5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbohydrazide

Hoong-Kun Fun,^a ^*‡ Suhana Arshad,^a Nithinchandra,^b Balakrishna Kalluraya ^b and J. H. S. Vidyashree ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangothri 574 199, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 17 May 2012; accepted 21 May 2012; online 26 May 2012)

In the title compound, C₁₇H₁₂Cl₂N₆O₃, the 1H-1,2,3-triazole ring [maximum deviation = 0.003 (1) Å] forms dihedral angles of 34.08 (6) and 28.38 (6)°, respectively, with the nitro- and dichloro-substituted benzene rings. The dihedral angle between the benzene rings is 6.68 (5)°. In the crystal, C—H⋯O hydrogen bonds link the molecules into chains running parallel to the a axis.

Related literature

For aryl hydrazones, see: Sridhar & Perumal (2003 ); Bedia et al. (2006 ); Rollas et al. (2002 ); Terzioglu & Gürsoy (2003 ). For related structures, see: Fun et al. (2011 ); Wang et al. (2010 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₇H₁₂Cl₂N₆O₃
M_r = 419.23
Monoclinic, P 2₁ /c
a = 6.6309 (3) Å
b = 22.7059 (10) Å
c = 13.3019 (5) Å
β = 119.559 (2)°
V = 1742.08 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 100 K
0.43 × 0.15 × 0.08 mm

Data collection

Bruker SMART APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.844, T_max = 0.967
38004 measured reflections
6085 independent reflections
5280 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.099
S = 1.04
6085 reflections
258 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O3ⁱ	0.93	2.41	3.2649 (17)	153
C12—H12A⋯O3ⁱ	0.93	2.59	3.4076 (15)	147
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812023112/hb6804sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023112/hb6804Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812023112/hb6804Isup3.cml

checkCIF report

Comment top

Aryl hydrazones are important building blocks for the synthesis of a variety of heterocyclic compounds such as pyrazolines and pyrazoles (Sridhar & Perumal, 2003). Aryl hydrazones have been most conveniently synthesized by the reaction of aryl hydrazines with carbonyl compounds. Hydrazones possessing an azomethine —NHN═CH— proton constitute an important class of compound for new drug development. Hydrazones have been demonstrated to possess anti-microbial, anti-convulsant, analgesic, anti-inflammatory, anti-platelet, anti-tubercular, anti-cancer and anti-tumoral activities (Bedia et al., 2006; Rollas et al., 2002; Terzioglu & Gürsoy, 2003). Prompted by these observations, the title compound was synthesized and its crystal structure is reported here.

The molecular structure is shown in Fig. 1. The 1H-1,2,3-triazole ring [N2–N4/C7/C8; maximum deviation of 0.003 (1) Å at atom N3] forms dihedral angles of 34.08 (6) and 28.38 (6)°, respectively with the nitro-substituted and dichloro-substituted phenyl rings (C1–C6 and C11–C16). The dihedral angle between the nitro-substituted (C1–C6) and dichloro-substituted (C11–C16) phenyl rings is 6.68 (5)°. Bond lengths and angles are within normal ranges and comparable to the related structures (Fun et al., 2011; Wang et al., 2010).

The crystal packing is shown in Fig. 2. The molecules are linked via intermolecular C10—H10A···O3 and C12—H12A···O3 hydrogen bonds (Table 1) into one-dimensional chain parallel to a-axis.

Related literature top

For aryl hydrazones, see: Sridhar & Perumal (2003); Bedia et al. (2006); Rollas et al. (2002); Terzioglu & Gürsoy (2003). For related structures, see: Fun et al. (2011); Wang et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was obtained by refluxing a mixture of 5-methyl-1- (4-nitrophenyl)-1H-1,2,3-triazole-4-carbohydrazide (0.01 mol), 3,4-dichlorobenzaldehyde (0.01 mol) in ethanol (30 ml) and 3 drops of concentrated sulfuric acid for 1 h. Excess ethanol was removed from the reaction mixture under reduced pressure. The solid product obtained was filtered, washed with ethanol and dried. Colourless plates were obtained by slow evaporation of an ethanol-N,N- dimethylformamide (DMF) (3:1) solution.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound, viewed down the c axis. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

N'-(3,4-Dichlorobenzylidene)-5-methyl-1-(4-nitrophenyl)-1H- 1,2,3-triazole-4-carbohydrazide top

Crystal data top

C₁₇H₁₂Cl₂N₆O₃	F(000) = 856
M_r = 419.23	D_x = 1.598 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9957 reflections
a = 6.6309 (3) Å	θ = 2.5–32.1°
b = 22.7059 (10) Å	µ = 0.41 mm⁻¹
c = 13.3019 (5) Å	T = 100 K
β = 119.559 (2)°	Plate, colourless
V = 1742.08 (13) Å³	0.43 × 0.15 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEX DUO CCD diffractometer	6085 independent reflections
Radiation source: fine-focus sealed tube	5280 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 32.1°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
T_min = 0.844, T_max = 0.967	k = −33→33
38004 measured reflections	l = −19→19

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0481P)² + 0.9914P] where P = (F_o² + 2F_c²)/3
6085 reflections	(Δ/σ)_max = 0.001
258 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₇H₁₂Cl₂N₆O₃	V = 1742.08 (13) Å³
M_r = 419.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.6309 (3) Å	µ = 0.41 mm⁻¹
b = 22.7059 (10) Å	T = 100 K
c = 13.3019 (5) Å	0.43 × 0.15 × 0.08 mm
β = 119.559 (2)°

Data collection top

Bruker SMART APEX DUO CCD diffractometer	6085 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5280 reflections with I > 2σ(I)
T_min = 0.844, T_max = 0.967	R_int = 0.030
38004 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.64 e Å⁻³
6085 reflections	Δρ_min = −0.46 e Å⁻³
258 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

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

	x	y	z	U_iso*/U_eq
Cl1	−0.56021 (5)	0.165386 (13)	0.28246 (3)	0.02116 (7)
Cl2	−0.03571 (5)	0.156467 (14)	0.34211 (3)	0.02223 (8)
O1	1.5942 (2)	−0.28578 (5)	1.52152 (10)	0.0388 (3)
O2	1.84421 (19)	−0.26840 (5)	1.46501 (9)	0.0319 (2)
O3	0.78124 (15)	−0.02047 (4)	0.78857 (7)	0.01839 (17)
N1	1.6545 (2)	−0.26107 (5)	1.45880 (10)	0.0250 (2)
N2	1.01583 (16)	−0.11155 (4)	1.10939 (8)	0.01214 (16)
N3	0.83699 (17)	−0.09041 (4)	1.12221 (8)	0.01438 (17)
N4	0.70655 (17)	−0.05895 (4)	1.03092 (8)	0.01456 (17)
N5	0.45947 (17)	−0.01568 (4)	0.81069 (8)	0.01497 (18)
N6	0.32662 (17)	0.01542 (4)	0.71002 (8)	0.01402 (17)
C1	1.4138 (2)	−0.14706 (5)	1.22695 (10)	0.0166 (2)
H1A	1.4642	−0.1214	1.1894	0.020*
C2	1.5691 (2)	−0.18447 (5)	1.31329 (10)	0.0188 (2)
H2A	1.7244	−0.1852	1.3327	0.023*
C3	1.4894 (2)	−0.22062 (5)	1.36985 (10)	0.0183 (2)
C4	1.2597 (2)	−0.22145 (5)	1.34402 (10)	0.0196 (2)
H4A	1.2119	−0.2453	1.3851	0.024*
C5	1.1028 (2)	−0.18563 (5)	1.25507 (10)	0.0165 (2)
H5A	0.9466	−0.1862	1.2339	0.020*
C6	1.18123 (19)	−0.14880 (5)	1.19790 (9)	0.01316 (19)
C7	0.99791 (19)	−0.09356 (5)	1.00752 (9)	0.01230 (18)
C8	0.79878 (19)	−0.05976 (5)	0.95886 (9)	0.01275 (18)
C9	0.68418 (19)	−0.02983 (5)	0.84506 (9)	0.01328 (19)
C10	0.1116 (2)	0.01900 (5)	0.68224 (9)	0.01384 (19)
H10A	0.0589	−0.0010	0.7258	0.017*
C11	−0.05113 (19)	0.05422 (5)	0.58286 (9)	0.01318 (18)
C12	−0.2838 (2)	0.05721 (5)	0.55521 (10)	0.0160 (2)
H12A	−0.3340	0.0366	0.5993	0.019*
C13	−0.4402 (2)	0.09107 (5)	0.46155 (10)	0.0179 (2)
H13A	−0.5953	0.0925	0.4423	0.021*
C14	−0.3645 (2)	0.12262 (5)	0.39687 (10)	0.0152 (2)
C15	−0.1323 (2)	0.11926 (5)	0.42388 (9)	0.01465 (19)
C16	0.0234 (2)	0.08516 (5)	0.51611 (9)	0.01451 (19)
H16A	0.1774	0.0828	0.5336	0.017*
C17	1.1550 (2)	−0.11109 (6)	0.96271 (10)	0.0177 (2)
H17A	1.0738	−0.1081	0.8799	0.027*
H17B	1.2053	−0.1510	0.9850	0.027*
H17C	1.2874	−0.0855	0.9942	0.027*
H1N5	0.406 (3)	−0.0207 (8)	0.8574 (16)	0.027 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01639 (13)	0.02378 (14)	0.02034 (14)	0.00532 (10)	0.00678 (11)	0.00923 (10)
Cl2	0.02019 (14)	0.02874 (15)	0.02075 (14)	0.00390 (11)	0.01239 (12)	0.01002 (10)
O1	0.0315 (6)	0.0358 (6)	0.0322 (6)	0.0003 (5)	0.0026 (5)	0.0195 (5)
O2	0.0246 (5)	0.0302 (5)	0.0272 (5)	0.0129 (4)	0.0023 (4)	0.0007 (4)
O3	0.0149 (4)	0.0252 (4)	0.0170 (4)	0.0007 (3)	0.0093 (3)	0.0048 (3)
N1	0.0232 (5)	0.0183 (5)	0.0197 (5)	0.0029 (4)	−0.0001 (4)	0.0014 (4)
N2	0.0103 (4)	0.0142 (4)	0.0116 (4)	0.0010 (3)	0.0051 (3)	0.0001 (3)
N3	0.0127 (4)	0.0173 (4)	0.0140 (4)	0.0033 (3)	0.0072 (3)	0.0011 (3)
N4	0.0131 (4)	0.0179 (4)	0.0131 (4)	0.0028 (3)	0.0067 (3)	0.0019 (3)
N5	0.0131 (4)	0.0208 (4)	0.0111 (4)	0.0039 (3)	0.0061 (3)	0.0044 (3)
N6	0.0137 (4)	0.0161 (4)	0.0103 (4)	0.0028 (3)	0.0045 (3)	0.0014 (3)
C1	0.0128 (5)	0.0183 (5)	0.0160 (5)	0.0002 (4)	0.0049 (4)	0.0005 (4)
C2	0.0126 (5)	0.0202 (5)	0.0182 (5)	0.0026 (4)	0.0035 (4)	−0.0007 (4)
C3	0.0175 (5)	0.0150 (5)	0.0135 (5)	0.0033 (4)	0.0007 (4)	0.0005 (4)
C4	0.0206 (6)	0.0176 (5)	0.0157 (5)	−0.0011 (4)	0.0052 (4)	0.0031 (4)
C5	0.0134 (5)	0.0186 (5)	0.0149 (5)	−0.0007 (4)	0.0051 (4)	0.0016 (4)
C6	0.0124 (5)	0.0128 (4)	0.0113 (4)	0.0010 (3)	0.0035 (4)	−0.0004 (3)
C7	0.0106 (4)	0.0142 (4)	0.0111 (4)	−0.0003 (3)	0.0047 (4)	−0.0001 (3)
C8	0.0105 (4)	0.0152 (4)	0.0122 (4)	0.0009 (3)	0.0053 (4)	0.0006 (3)
C9	0.0118 (5)	0.0149 (4)	0.0121 (4)	0.0004 (4)	0.0051 (4)	0.0005 (3)
C10	0.0143 (5)	0.0147 (4)	0.0120 (4)	0.0010 (4)	0.0062 (4)	0.0001 (3)
C11	0.0127 (5)	0.0142 (4)	0.0112 (4)	0.0010 (4)	0.0048 (4)	−0.0003 (3)
C12	0.0134 (5)	0.0183 (5)	0.0153 (5)	0.0006 (4)	0.0062 (4)	0.0029 (4)
C13	0.0121 (5)	0.0217 (5)	0.0189 (5)	0.0016 (4)	0.0070 (4)	0.0046 (4)
C14	0.0141 (5)	0.0159 (4)	0.0140 (4)	0.0020 (4)	0.0057 (4)	0.0020 (4)
C15	0.0162 (5)	0.0153 (4)	0.0136 (4)	0.0005 (4)	0.0083 (4)	0.0012 (3)
C16	0.0137 (5)	0.0167 (4)	0.0133 (4)	0.0013 (4)	0.0067 (4)	0.0003 (3)
C17	0.0139 (5)	0.0250 (5)	0.0169 (5)	0.0030 (4)	0.0096 (4)	0.0012 (4)

Geometric parameters (Å, º) top

Cl1—C14	1.7305 (11)	C4—C5	1.3889 (16)
Cl2—C15	1.7304 (11)	C4—H4A	0.9300
O1—N1	1.2248 (17)	C5—C6	1.3920 (16)
O2—N1	1.2303 (17)	C5—H5A	0.9300
O3—C9	1.2252 (14)	C7—C8	1.3813 (15)
N1—C3	1.4711 (15)	C7—C17	1.4874 (16)
N2—C7	1.3631 (14)	C8—C9	1.4818 (15)
N2—N3	1.3658 (13)	C10—C11	1.4642 (15)
N2—C6	1.4249 (14)	C10—H10A	0.9300
N3—N4	1.3024 (13)	C11—C16	1.3998 (15)
N4—C8	1.3681 (14)	C11—C12	1.4000 (16)
N5—C9	1.3640 (14)	C12—C13	1.3941 (16)
N5—N6	1.3799 (13)	C12—H12A	0.9300
N5—H1N5	0.863 (19)	C13—C14	1.3897 (16)
N6—C10	1.2871 (15)	C13—H13A	0.9300
C1—C2	1.3906 (16)	C14—C15	1.4001 (16)
C1—C6	1.3935 (16)	C15—C16	1.3858 (15)
C1—H1A	0.9300	C16—H16A	0.9300
C2—C3	1.3824 (18)	C17—H17A	0.9600
C2—H2A	0.9300	C17—H17B	0.9600
C3—C4	1.3869 (18)	C17—H17C	0.9600

O1—N1—O2	123.98 (12)	N4—C8—C7	109.48 (9)
O1—N1—C3	118.05 (12)	N4—C8—C9	121.89 (10)
O2—N1—C3	117.97 (12)	C7—C8—C9	128.57 (10)
C7—N2—N3	111.32 (9)	O3—C9—N5	124.82 (10)
C7—N2—C6	130.79 (9)	O3—C9—C8	123.11 (10)
N3—N2—C6	117.85 (9)	N5—C9—C8	112.05 (9)
N4—N3—N2	107.12 (9)	N6—C10—C11	120.81 (10)
N3—N4—C8	108.97 (9)	N6—C10—H10A	119.6
C9—N5—N6	120.97 (9)	C11—C10—H10A	119.6
C9—N5—H1N5	120.0 (12)	C16—C11—C12	119.81 (10)
N6—N5—H1N5	118.2 (12)	C16—C11—C10	120.89 (10)
C10—N6—N5	113.41 (10)	C12—C11—C10	119.30 (10)
C2—C1—C6	118.62 (11)	C13—C12—C11	119.94 (11)
C2—C1—H1A	120.7	C13—C12—H12A	120.0
C6—C1—H1A	120.7	C11—C12—H12A	120.0
C3—C2—C1	119.09 (11)	C14—C13—C12	120.06 (11)
C3—C2—H2A	120.5	C14—C13—H13A	120.0
C1—C2—H2A	120.5	C12—C13—H13A	120.0
C2—C3—C4	122.77 (11)	C13—C14—C15	120.02 (10)
C2—C3—N1	118.42 (11)	C13—C14—Cl1	119.38 (9)
C4—C3—N1	118.78 (11)	C15—C14—Cl1	120.60 (9)
C3—C4—C5	118.19 (11)	C16—C15—C14	120.16 (10)
C3—C4—H4A	120.9	C16—C15—Cl2	118.96 (9)
C5—C4—H4A	120.9	C14—C15—Cl2	120.88 (8)
C4—C5—C6	119.53 (11)	C15—C16—C11	120.00 (10)
C4—C5—H5A	120.2	C15—C16—H16A	120.0
C6—C5—H5A	120.2	C11—C16—H16A	120.0
C5—C6—C1	121.73 (10)	C7—C17—H17A	109.5
C5—C6—N2	117.74 (10)	C7—C17—H17B	109.5
C1—C6—N2	120.52 (10)	H17A—C17—H17B	109.5
N2—C7—C8	103.11 (9)	C7—C17—H17C	109.5
N2—C7—C17	125.69 (10)	H17A—C17—H17C	109.5
C8—C7—C17	131.11 (10)	H17B—C17—H17C	109.5

C7—N2—N3—N4	−0.47 (12)	N3—N4—C8—C9	177.51 (10)
C6—N2—N3—N4	−178.56 (9)	N2—C7—C8—N4	−0.28 (12)
N2—N3—N4—C8	0.28 (12)	C17—C7—C8—N4	176.31 (11)
C9—N5—N6—C10	171.91 (10)	N2—C7—C8—C9	−177.56 (10)
C6—C1—C2—C3	−2.09 (17)	C17—C7—C8—C9	−1.0 (2)
C1—C2—C3—C4	0.21 (18)	N6—N5—C9—O3	−5.22 (17)
C1—C2—C3—N1	178.39 (11)	N6—N5—C9—C8	176.32 (9)
O1—N1—C3—C2	168.22 (12)	N4—C8—C9—O3	166.12 (11)
O2—N1—C3—C2	−12.38 (17)	C7—C8—C9—O3	−16.90 (18)
O1—N1—C3—C4	−13.52 (18)	N4—C8—C9—N5	−15.39 (15)
O2—N1—C3—C4	165.87 (12)	C7—C8—C9—N5	161.59 (11)
C2—C3—C4—C5	2.01 (18)	N5—N6—C10—C11	175.27 (9)
N1—C3—C4—C5	−176.16 (11)	N6—C10—C11—C16	−0.42 (16)
C3—C4—C5—C6	−2.29 (18)	N6—C10—C11—C12	−179.89 (10)
C4—C5—C6—C1	0.43 (17)	C16—C11—C12—C13	−0.14 (17)
C4—C5—C6—N2	−178.26 (10)	C10—C11—C12—C13	179.34 (10)
C2—C1—C6—C5	1.80 (17)	C11—C12—C13—C14	−1.09 (18)
C2—C1—C6—N2	−179.55 (10)	C12—C13—C14—C15	1.62 (18)
C7—N2—C6—C5	−144.57 (12)	C12—C13—C14—Cl1	−178.90 (9)
N3—N2—C6—C5	33.08 (14)	C13—C14—C15—C16	−0.91 (17)
C7—N2—C6—C1	36.73 (17)	Cl1—C14—C15—C16	179.61 (9)
N3—N2—C6—C1	−145.62 (11)	C13—C14—C15—Cl2	178.15 (9)
N3—N2—C7—C8	0.46 (12)	Cl1—C14—C15—Cl2	−1.32 (14)
C6—N2—C7—C8	178.23 (10)	C14—C15—C16—C11	−0.32 (17)
N3—N2—C7—C17	−176.38 (10)	Cl2—C15—C16—C11	−179.41 (8)
C6—N2—C7—C17	1.40 (18)	C12—C11—C16—C15	0.84 (16)
N3—N4—C8—C7	0.01 (13)	C10—C11—C16—C15	−178.62 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O3ⁱ	0.93	2.41	3.2649 (17)	153
C12—H12A···O3ⁱ	0.93	2.59	3.4076 (15)	147

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₂Cl₂N₆O₃
M_r	419.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	6.6309 (3), 22.7059 (10), 13.3019 (5)
β (°)	119.559 (2)
V (Å³)	1742.08 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.43 × 0.15 × 0.08

Data collection
Diffractometer	Bruker SMART APEX DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.844, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	38004, 6085, 5280
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.748

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.099, 1.04
No. of reflections	6085
No. of parameters	258
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.46

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O3ⁱ	0.93	2.41	3.2649 (17)	153
C12—H12A···O3ⁱ	0.93	2.59	3.4076 (15)	147

Symmetry code: (i) x−1, y, z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). SA also thanks the Malaysian Government and USM for the Academic Staff Training Scheme (ASTS) award. BK is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for financial assistance.

References

Bedia, K.-K., Elçin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253–1261. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Quah, C. K., Nithinchandra, & Kalluraya, B. (2011). Acta Cryst. E67, o2416. Google Scholar
Rollas, S., Gülerman, N. & Erdeniz, H. (2002). Farmaco, 57, 171–174. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N′-(3,4-Di­chloro­benzyl­­idene)-5-methyl-1-(4-nitro­phen­yl)-1H-1,2,3-triazole-4-carbohydrazide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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Acknowledgements

References

organic compounds

N′-(3,4-Dichlorobenzylidene)-5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbohydrazide