N′-[1-(4-Chloro­phen­yl)ethyl­idene]-5-methyl-1-(4-nitro­phen­yl)-1H-1,2,3-triazole-4-carbohydrazide

Fun, H.-K.; Quah, C.K.; Nitinchandra; Kalluraya, B.; Shetty, S.

doi:10.1107/S1600536812027535

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2164

https://doi.org/10.1107/S1600536812027535

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N′-[1-(4-Chlorophenyl)ethylidene]-5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbohydrazide

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Nitinchandra,^b Balakrishna Kalluraya ^b and Shobhitha Shetty ^b

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

(Received 11 June 2012; accepted 18 June 2012; online 23 June 2012)

In the title compound, C₁₈H₁₅ClN₆O₃, 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, molecules 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_r = 398.81
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.120
S = 1.03
7839 reflections
259 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.45 e Å⁻³

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) x, y-1, 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: https://doi.org/10.1107/S1600536812027535/is5158sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027535/is5158Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812027535/is5158Isup3.cml

checkCIF report

Comment top

1,2,3-Triazole and its derivatives had attracted considerable attention for the past few decades due to their chemotherapeutic value. Many 1,2,3-triazoles are found to be potent antimicrobial (Sherement et al., 2004) and antiviral agents. Some of them have exhibited antiproliferative and anticancer activities (Danoun et al., 1998). Some 1,2,3-triazoles are used as DNA cleaving agents (Manfredini et al., 2000) and potassium channel activators (Biagi et al., 2004). Hydrazones derived from anisaldehyde and 4-nitro-5-ethoxycarbonyl phenylhydrazine showed excellent NLO property (Vijayakumar et al., 2011). Prompted by these observation, we synthesized new hydrazone carrying 1,2,3-triazoles nucleus.

In the title molecule, Fig. 1, the mean plane of 1,2,3-triazole ring (N3-N5/C9/C10, r.m.s deviation = 0.002 Å) forms dihedral angles of 15.64 (5) and 57.50 (5)° with the two benzene rings (C1–C6 and C11–C16). The dihedral angle between the two benzenel rings is 72.26 (5)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun, Quah, Chandrakantha et al., 2011; Fun et al., 2011a,b). In the crystal (Fig. 2), molecules are linked via intermolecular C13—H13A···O1 hydrogen bonds (Table 1) into chains propagating along [010]. A short O2···C7 contact of 2.9972 (13) Å also occurs.

Related literature top

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 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) and p-chloroacetophenone (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. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol-N,N-dimethylformamide (DMF) (3:1) solution.

Structure description top

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).

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 for non-H atoms.
	Fig. 2. A packing diagram of the title compound, viewed along the c axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

N'-[1-(4-Chlorophenyl)ethylidene]-5-methyl-1-(4-nitrophenyl)-1H- 1,2,3-triazole-4-carbohydrazide top

Crystal data top

C₁₈H₁₅ClN₆O₃	Z = 2
M_r = 398.81	F(000) = 412
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.041	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(F_o²) + (0.0635P)² + 0.2969P] where P = (F_o² + 2F_c²)/3
7839 reflections	(Δ/σ)_max = 0.001
259 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₈H₁₅ClN₆O₃	γ = 76.373 (1)°
M_r = 398.81	V = 887.84 (2) Å³
Triclinic, P1	Z = 2
a = 8.6603 (1) Å	Mo Kα radiation
b = 10.2844 (1) Å	µ = 0.25 mm⁻¹
c = 10.4033 (1) Å	T = 100 K
α = 83.816 (1)°	0.31 × 0.19 × 0.17 mm
β = 81.402 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7839 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6598 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.958	R_int = 0.023
29293 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.56 e Å⁻³
7839 reflections	Δρ_min = −0.45 e Å⁻³
259 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 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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅ClN₆O₃
M_r	398.81
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.6603 (1), 10.2844 (1), 10.4033 (1)
α, β, γ (°)	83.816 (1), 81.402 (1), 76.373 (1)
V (Å³)	887.84 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.31 × 0.19 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.927, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	29293, 7839, 6598
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.812

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.120, 1.03
No. of reflections	7839
No. of parameters	259
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.45

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

Symmetry code: (i) x, y−1, z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). CKQ also thanks USM for an Incentive Grant. BK thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for financial assistance.

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