N'-[1-(4-Chloro-phen-yl)ethyl-idene]-5-methyl-1-(4-nitro-phen-yl)-1H-1,2,3-triazole-4-carbohydrazide.

In the title compound, C(18)H(15)ClN(6)O(3), the 1,2,3-triazole ring forms dihedral angles of 15.64 (5) and 57.50 (5)° with the two benzene rings. The dihedral angle between the two benzene rings is 72.26 (5)°. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds into chains propagating along the b axis. A short O⋯C contact of 2.9972 (13) Å is observed.

Related literature

For general background to and the biological activity of triazole derivatives, see: Sherement et al. (2004 ▶); Danoun et al. (1998 ▶); Manfredini et al. (2000 ▶); Biagi et al. (2004 ▶); Vijayakumar et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For related structures, see: Fun, Quah, Chandrakantha et al. (2011 ▶); Fun et al. (2011a ▶,b ▶).

Experimental

Crystal data

C18H15ClN6O3

M = 398.81

Triclinic,

a = 8.6603 (1) Å

b = 10.2844 (1) Å

c = 10.4033 (1) Å

α = 83.816 (1)°

β = 81.402 (1)°

γ = 76.373 (1)°

V = 887.84 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 100 K

0.31 × 0.19 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.927, T max = 0.958

29293 measured reflections

7839 independent reflections

6598 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.120

S = 1.03

7839 reflections

259 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.56 e Å−3

Δρmin = −0.45 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/S1600536812027535/is5158sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027535/is5158Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027535/is5158Isup3.cml

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

C18H15ClN6O3	Z = 2
Mr = 398.81	F(000) = 412
Triclinic, P1	Dx = 1.492 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6603 (1) Å	Cell parameters from 9924 reflections
b = 10.2844 (1) Å	θ = 2.4–35.1°
c = 10.4033 (1) Å	µ = 0.25 mm−1
α = 83.816 (1)°	T = 100 K
β = 81.402 (1)°	Block, yellow
γ = 76.373 (1)°	0.31 × 0.19 × 0.17 mm
V = 887.84 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	7839 independent reflections
Radiation source: fine-focus sealed tube	6598 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 35.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→13
Tmin = 0.927, Tmax = 0.958	k = −16→16
29293 measured reflections	l = −16→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0635P)2 + 0.2969P] where P = (Fo2 + 2Fc2)/3
7839 reflections	(Δ/σ)max = 0.001
259 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.45 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.07731 (3)	1.51350 (2)	0.15822 (3)	0.02455 (7)
O1	0.43782 (9)	0.74131 (7)	0.59589 (7)	0.01901 (13)
O2	0.30629 (12)	−0.13446 (9)	1.10163 (8)	0.0326 (2)
O3	0.38384 (15)	−0.24022 (8)	0.92733 (9)	0.0389 (2)
N1	0.21957 (10)	0.88716 (7)	0.43384 (8)	0.01537 (13)
N2	0.23356 (10)	0.75384 (8)	0.47404 (8)	0.01648 (14)
N3	0.23287 (10)	0.49322 (8)	0.53284 (8)	0.01770 (14)
N4	0.23488 (11)	0.37257 (8)	0.58529 (8)	0.01845 (15)
N5	0.32874 (10)	0.35228 (7)	0.68349 (7)	0.01458 (13)
N6	0.34560 (11)	−0.13715 (8)	0.98386 (9)	0.01954 (15)
C1	0.20505 (11)	1.15159 (9)	0.34403 (9)	0.01614 (15)
H1A	0.2840	1.1076	0.3981	0.019*
C2	0.19901 (12)	1.28429 (9)	0.29798 (9)	0.01779 (16)
H2A	0.2732	1.3307	0.3197	0.021*
C3	0.08252 (12)	1.34817 (9)	0.21943 (9)	0.01661 (15)
C4	−0.02861 (12)	1.28298 (9)	0.18865 (10)	0.01829 (16)
H4A	−0.1087	1.3283	0.1362	0.022*
C5	−0.02088 (11)	1.14978 (9)	0.23606 (9)	0.01716 (15)
H5A	−0.0974	1.1048	0.2161	0.021*
C6	0.09732 (10)	1.08100 (9)	0.31252 (8)	0.01409 (14)
C7	0.11168 (11)	0.93734 (9)	0.35781 (9)	0.01475 (14)
C8	0.34084 (11)	0.69073 (8)	0.55704 (8)	0.01471 (14)
C9	0.32483 (11)	0.55123 (8)	0.59531 (8)	0.01430 (14)
C10	0.38769 (11)	0.46173 (9)	0.69309 (9)	0.01486 (15)
C11	0.34388 (11)	0.22838 (8)	0.76168 (8)	0.01399 (14)
C12	0.40005 (11)	0.10949 (9)	0.70018 (9)	0.01562 (15)
H12A	0.4375	0.1114	0.6095	0.019*
C13	0.40066 (11)	−0.01205 (9)	0.77318 (9)	0.01625 (15)
H13A	0.4358	−0.0947	0.7334	0.019*
C14	0.34846 (11)	−0.00917 (9)	0.90596 (9)	0.01519 (15)
C15	0.29653 (12)	0.10859 (9)	0.96930 (9)	0.01683 (15)
H15A	0.2643	0.1063	1.0607	0.020*
C16	0.29298 (11)	0.22988 (9)	0.89527 (9)	0.01648 (15)
H16A	0.2565	0.3125	0.9350	0.020*
C17	0.00858 (14)	0.85722 (11)	0.31287 (12)	0.0258 (2)
H17A	0.0763	0.7751	0.2777	0.039*
H17B	−0.0510	0.9106	0.2449	0.039*
H17C	−0.0669	0.8336	0.3867	0.039*
C18	0.49787 (15)	0.46863 (11)	0.78744 (11)	0.0260 (2)
H18A	0.5705	0.3807	0.7998	0.039*
H18B	0.4354	0.4940	0.8711	0.039*
H18C	0.5604	0.5357	0.7537	0.039*
H1N2	0.166 (2)	0.7102 (18)	0.4563 (17)	0.036 (4)*

	U11	U22	U33	U12	U13	U23
Cl1	0.03489 (14)	0.01270 (10)	0.02708 (12)	−0.00533 (8)	−0.01090 (10)	0.00374 (8)
O1	0.0224 (3)	0.0150 (3)	0.0216 (3)	−0.0064 (2)	−0.0073 (3)	0.0008 (2)
O2	0.0440 (5)	0.0211 (4)	0.0239 (4)	−0.0016 (3)	0.0085 (3)	0.0065 (3)
O3	0.0768 (8)	0.0139 (3)	0.0274 (4)	−0.0118 (4)	−0.0103 (4)	0.0005 (3)
N1	0.0177 (3)	0.0118 (3)	0.0165 (3)	−0.0038 (2)	−0.0032 (3)	0.0019 (2)
N2	0.0197 (3)	0.0118 (3)	0.0190 (3)	−0.0052 (3)	−0.0061 (3)	0.0030 (2)
N3	0.0223 (4)	0.0151 (3)	0.0175 (3)	−0.0071 (3)	−0.0062 (3)	0.0025 (3)
N4	0.0239 (4)	0.0161 (3)	0.0177 (3)	−0.0078 (3)	−0.0080 (3)	0.0032 (3)
N5	0.0180 (3)	0.0123 (3)	0.0144 (3)	−0.0048 (2)	−0.0041 (2)	0.0008 (2)
N6	0.0214 (4)	0.0149 (3)	0.0222 (4)	−0.0047 (3)	−0.0045 (3)	0.0032 (3)
C1	0.0186 (4)	0.0148 (3)	0.0159 (3)	−0.0048 (3)	−0.0054 (3)	0.0018 (3)
C2	0.0225 (4)	0.0148 (3)	0.0177 (4)	−0.0060 (3)	−0.0061 (3)	0.0006 (3)
C3	0.0208 (4)	0.0115 (3)	0.0166 (4)	−0.0023 (3)	−0.0031 (3)	0.0006 (3)
C4	0.0178 (4)	0.0159 (4)	0.0203 (4)	−0.0016 (3)	−0.0055 (3)	0.0019 (3)
C5	0.0156 (4)	0.0161 (4)	0.0201 (4)	−0.0041 (3)	−0.0045 (3)	0.0018 (3)
C6	0.0143 (3)	0.0132 (3)	0.0143 (3)	−0.0033 (3)	−0.0014 (3)	0.0009 (3)
C7	0.0149 (3)	0.0139 (3)	0.0156 (3)	−0.0046 (3)	−0.0023 (3)	0.0016 (3)
C8	0.0177 (4)	0.0120 (3)	0.0138 (3)	−0.0031 (3)	−0.0016 (3)	0.0006 (3)
C9	0.0166 (3)	0.0121 (3)	0.0145 (3)	−0.0040 (3)	−0.0029 (3)	0.0007 (3)
C10	0.0172 (4)	0.0119 (3)	0.0160 (3)	−0.0039 (3)	−0.0037 (3)	0.0002 (3)
C11	0.0155 (3)	0.0119 (3)	0.0147 (3)	−0.0040 (3)	−0.0025 (3)	0.0011 (3)
C12	0.0182 (4)	0.0138 (3)	0.0149 (3)	−0.0039 (3)	−0.0016 (3)	−0.0009 (3)
C13	0.0186 (4)	0.0127 (3)	0.0175 (4)	−0.0034 (3)	−0.0028 (3)	−0.0007 (3)
C14	0.0159 (3)	0.0120 (3)	0.0176 (4)	−0.0038 (3)	−0.0029 (3)	0.0020 (3)
C15	0.0193 (4)	0.0148 (3)	0.0151 (3)	−0.0032 (3)	−0.0004 (3)	0.0007 (3)
C16	0.0202 (4)	0.0127 (3)	0.0155 (4)	−0.0027 (3)	−0.0008 (3)	−0.0007 (3)
C17	0.0286 (5)	0.0222 (4)	0.0321 (5)	−0.0143 (4)	−0.0149 (4)	0.0086 (4)
C18	0.0358 (6)	0.0183 (4)	0.0299 (5)	−0.0112 (4)	−0.0197 (4)	0.0046 (4)

Cl1—C3	1.7429 (9)	C5—H5A	0.9500
O1—C8	1.2214 (11)	C6—C7	1.4836 (12)
O2—N6	1.2231 (12)	C7—C17	1.4998 (14)
O3—N6	1.2205 (12)	C8—C9	1.4799 (12)
N1—C7	1.2926 (12)	C9—C10	1.3806 (12)
N1—N2	1.3722 (10)	C10—C18	1.4852 (13)
N2—C8	1.3657 (12)	C11—C12	1.3915 (12)
N2—H1N2	0.870 (18)	C11—C16	1.3943 (12)
N3—N4	1.2979 (11)	C12—C13	1.3903 (12)
N3—C9	1.3692 (12)	C12—H12A	0.9500
N4—N5	1.3676 (11)	C13—C14	1.3889 (13)
N5—C10	1.3594 (11)	C13—H13A	0.9500
N5—C11	1.4257 (11)	C14—C15	1.3892 (13)
N6—C14	1.4728 (12)	C15—C16	1.3900 (12)
C1—C2	1.3884 (12)	C15—H15A	0.9500
C1—C6	1.4025 (13)	C16—H16A	0.9500
C1—H1A	0.9500	C17—H17A	0.9800
C2—C3	1.3912 (13)	C17—H17B	0.9800
C2—H2A	0.9500	C17—H17C	0.9800
C3—C4	1.3859 (14)	C18—H18A	0.9800
C4—C5	1.3948 (13)	C18—H18B	0.9800
C4—H4A	0.9500	C18—H18C	0.9800
C5—C6	1.4007 (13)
C7—N1—N2	115.65 (8)	N3—C9—C10	109.28 (8)
C8—N2—N1	120.88 (8)	N3—C9—C8	120.79 (8)
C8—N2—H1N2	117.8 (12)	C10—C9—C8	129.91 (8)
N1—N2—H1N2	120.8 (12)	N5—C10—C9	103.05 (8)
N4—N3—C9	109.30 (8)	N5—C10—C18	124.22 (8)
N3—N4—N5	106.77 (7)	C9—C10—C18	132.69 (9)
C10—N5—N4	111.60 (7)	C12—C11—C16	122.23 (8)
C10—N5—C11	130.38 (8)	C12—C11—N5	118.44 (8)
N4—N5—C11	117.94 (7)	C16—C11—N5	119.21 (8)
O3—N6—O2	123.62 (9)	C13—C12—C11	119.11 (8)
O3—N6—C14	118.11 (9)	C13—C12—H12A	120.4
O2—N6—C14	118.27 (8)	C11—C12—H12A	120.4
C2—C1—C6	121.50 (8)	C14—C13—C12	118.08 (8)
C2—C1—H1A	119.3	C14—C13—H13A	121.0
C6—C1—H1A	119.3	C12—C13—H13A	121.0
C1—C2—C3	118.88 (9)	C13—C14—C15	123.40 (8)
C1—C2—H2A	120.6	C13—C14—N6	118.58 (8)
C3—C2—H2A	120.6	C15—C14—N6	118.02 (8)
C4—C3—C2	121.41 (8)	C14—C15—C16	118.22 (8)
C4—C3—Cl1	119.51 (7)	C14—C15—H15A	120.9
C2—C3—Cl1	119.08 (7)	C16—C15—H15A	120.9
C3—C4—C5	118.87 (8)	C15—C16—C11	118.92 (8)
C3—C4—H4A	120.6	C15—C16—H16A	120.5
C5—C4—H4A	120.6	C11—C16—H16A	120.5
C4—C5—C6	121.37 (9)	C7—C17—H17A	109.5
C4—C5—H5A	119.3	C7—C17—H17B	109.5
C6—C5—H5A	119.3	H17A—C17—H17B	109.5
C5—C6—C1	117.93 (8)	C7—C17—H17C	109.5
C5—C6—C7	121.78 (8)	H17A—C17—H17C	109.5
C1—C6—C7	120.28 (8)	H17B—C17—H17C	109.5
N1—C7—C6	115.96 (8)	C10—C18—H18A	109.5
N1—C7—C17	123.38 (8)	C10—C18—H18B	109.5
C6—C7—C17	120.63 (8)	H18A—C18—H18B	109.5
O1—C8—N2	125.21 (8)	C10—C18—H18C	109.5
O1—C8—C9	123.63 (8)	H18A—C18—H18C	109.5
N2—C8—C9	111.15 (8)	H18B—C18—H18C	109.5
C7—N1—N2—C8	−178.43 (8)	N2—C8—C9—C10	−167.16 (9)
C9—N3—N4—N5	0.29 (10)	N4—N5—C10—C9	0.09 (10)
N3—N4—N5—C10	−0.24 (11)	C11—N5—C10—C9	−176.51 (9)
N3—N4—N5—C11	176.83 (8)	N4—N5—C10—C18	−177.85 (10)
C6—C1—C2—C3	0.35 (14)	C11—N5—C10—C18	5.55 (16)
C1—C2—C3—C4	1.24 (14)	N3—C9—C10—N5	0.09 (10)
C1—C2—C3—Cl1	−178.52 (7)	C8—C9—C10—N5	178.30 (9)
C2—C3—C4—C5	−1.10 (14)	N3—C9—C10—C18	177.77 (11)
Cl1—C3—C4—C5	178.66 (7)	C8—C9—C10—C18	−4.03 (18)
C3—C4—C5—C6	−0.64 (14)	C10—N5—C11—C12	−126.78 (10)
C4—C5—C6—C1	2.15 (14)	N4—N5—C11—C12	56.80 (12)
C4—C5—C6—C7	−176.84 (9)	C10—N5—C11—C16	57.15 (13)
C2—C1—C6—C5	−2.00 (14)	N4—N5—C11—C16	−119.27 (10)
C2—C1—C6—C7	177.00 (8)	C16—C11—C12—C13	2.20 (14)
N2—N1—C7—C6	−179.22 (7)	N5—C11—C12—C13	−173.74 (8)
N2—N1—C7—C17	−1.02 (14)	C11—C12—C13—C14	−1.61 (13)
C5—C6—C7—N1	−176.20 (8)	C12—C13—C14—C15	−0.29 (14)
C1—C6—C7—N1	4.84 (13)	C12—C13—C14—N6	178.83 (8)
C5—C6—C7—C17	5.55 (14)	O3—N6—C14—C13	−2.62 (14)
C1—C6—C7—C17	−173.42 (9)	O2—N6—C14—C13	176.82 (10)
N1—N2—C8—O1	−4.64 (14)	O3—N6—C14—C15	176.54 (10)
N1—N2—C8—C9	175.17 (8)	O2—N6—C14—C15	−4.02 (14)
N4—N3—C9—C10	−0.25 (11)	C13—C14—C15—C16	1.63 (15)
N4—N3—C9—C8	−178.64 (8)	N6—C14—C15—C16	−177.48 (8)
O1—C8—C9—N3	−169.32 (9)	C14—C15—C16—C11	−1.05 (14)
N2—C8—C9—N3	10.87 (12)	C12—C11—C16—C15	−0.83 (14)
O1—C8—C9—C10	12.66 (16)	N5—C11—C16—C15	175.08 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1i	0.95	2.32	3.2226 (12)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1i	0.95	2.32	3.2226 (12)	158

Symmetry code: (i) .