N'-(3,4-Dichloro-benzyl-idene)-5-methyl-1-(4-nitro-phen-yl)-1H-1,2,3-triazole-4-carbohydrazide.

In the title compound, C(17)H(12)Cl(2)N(6)O(3), 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 mol-ecules 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 = 419.23

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.099

S = 1.04

6085 reflections

258 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.64 e Å−3

Δρmin = −0.46 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023112/hb6804sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812023112/hb6804Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H12Cl2N6O3	F(000) = 856
Mr = 419.23	Dx = 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

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

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(Fo2) + (0.0481P)2 + 0.9914P] where P = (Fo2 + 2Fc2)/3
6085 reflections	(Δ/σ)max = 0.001
258 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) .