2-(4-Chloro­anilino)quinoxaline

Idris, A.; Wan Saffiee, W.A.M.; Abdullah, Z.; Ariffin, A.; Ng, S.W.

doi:10.1107/S1600536808038610

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2443

doi:10.1107/S1600536808038610

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2-(4-Chloroanilino)quinoxaline

Azila Idris,^a Wan Ainna Mardhiah Wan Saffiee,^a Zanariah Abdullah,^a Azahar Ariffin ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 18 November 2008; accepted 19 November 2008; online 26 November 2008)

There are two molecules in the asymmetric unit of the title compound, C₁₄H₁₀ClN₃, with dihedral angles of 5.11 (10) and 13.61 (10)° between the aromatic ring systems. In the crystal structure, molecules are linked by N—H⋯N hydrogen bonds, resulting in chains propagating in [010].

Related literature

For the structure of 2-N-(4-chloroanilino)pyridine, see: Fairuz et al. (2008 ).

Experimental

Crystal data

C₁₄H₁₀ClN₃
M_r = 255.70
Orthorhombic, P b c a
a = 12.155 (1) Å
b = 11.238 (1) Å
c = 35.421 (3) Å
V = 4838.3 (8) Å³
Z = 16
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 100 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.916, T_max = 0.971
25622 measured reflections
5495 independent reflections
4111 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.135
S = 1.07
5495 reflections
331 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N6	0.88 (1)	2.24 (1)	3.086 (3)	160 (3)
N4—H4⋯N3ⁱ	0.88 (1)	2.19 (2)	3.010 (3)	155 (3)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038610/hb2854sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038610/hb2854Isup2.hkl

checkCIF report

Comment top

See the Abstract for details of the title compound, (I), (Fig. 1). See Table 1 for hydrogen bond information. For a related structure, see: Fairuz et al. (2008).

Related literature top

For the structure of 2-N-(4-chloroanilino)pyridine, see: Fairuz et al. (2008).

Experimental top

Chloroquinoxaline (0.33 g, 0.2 mmol) and 4-chloroaniline (0.25 g, 0.2 mmol) were heated at 423–433 K for 5 h. The mixture was cooled and dissolved in water. The solution was extracted with chloroform. The chloroform extract was dried over sodium sulfate and the solvent evaporated. The product was recrystallized from chloroform to yield colourless prisms of (I).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

Fig. 1. The molecular structure of (I) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

2-(4-Chloroanilino)quinoxaline top

Crystal data top

C₁₄H₁₀ClN₃	F(000) = 2112
M_r = 255.70	D_x = 1.404 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3986 reflections
a = 12.155 (1) Å	θ = 2.5–27.8°
b = 11.238 (1) Å	µ = 0.30 mm⁻¹
c = 35.421 (3) Å	T = 100 K
V = 4838.3 (8) Å³	Prism, colourless
Z = 16	0.30 × 0.20 × 0.10 mm

Data collection top

Bruker SMART APEX CCD diffractometer	5495 independent reflections
Radiation source: fine-focus sealed tube	4111 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
ω scans	θ_max = 27.5°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.916, T_max = 0.971	k = −14→14
25622 measured reflections	l = −34→45

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0485P)² + 5.0859P] where P = (F_o² + 2F_c²)/3
5495 reflections	(Δ/σ)_max = 0.001
331 parameters	Δρ_max = 0.31 e Å⁻³
2 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₄H₁₀ClN₃	V = 4838.3 (8) Å³
M_r = 255.70	Z = 16
Orthorhombic, Pbca	Mo Kα radiation
a = 12.155 (1) Å	µ = 0.30 mm⁻¹
b = 11.238 (1) Å	T = 100 K
c = 35.421 (3) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Bruker SMART APEX CCD diffractometer	5495 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4111 reflections with I > 2σ(I)
T_min = 0.916, T_max = 0.971	R_int = 0.066
25622 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	2 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.31 e Å⁻³
5495 reflections	Δρ_min = −0.28 e Å⁻³
331 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.71730 (5)	0.59065 (6)	0.569356 (19)	0.02492 (17)
Cl2	0.02845 (6)	0.18094 (7)	0.22911 (2)	0.03264 (19)
N1	0.51639 (18)	0.8613 (2)	0.44328 (6)	0.0193 (5)
H1	0.481 (2)	0.813 (2)	0.4277 (7)	0.023*
N2	0.59094 (17)	1.05427 (18)	0.44793 (6)	0.0167 (4)
N3	0.45895 (17)	1.11409 (19)	0.38437 (6)	0.0176 (5)
N4	0.22121 (17)	0.54504 (19)	0.33035 (6)	0.0192 (5)
H4	0.1703 (18)	0.586 (2)	0.3421 (7)	0.023*
N5	0.41121 (17)	0.5347 (2)	0.31927 (6)	0.0198 (5)
N6	0.43633 (18)	0.7150 (2)	0.37487 (6)	0.0216 (5)
C1	0.56706 (19)	0.8032 (2)	0.47383 (7)	0.0171 (5)
C2	0.6235 (2)	0.8609 (2)	0.50277 (7)	0.0174 (5)
H2	0.6304	0.9451	0.5026	0.021*
C3	0.6698 (2)	0.7948 (2)	0.53204 (7)	0.0192 (5)
H3	0.7084	0.8341	0.5518	0.023*
C4	0.6597 (2)	0.6723 (2)	0.53243 (7)	0.0196 (5)
C5	0.6043 (2)	0.6133 (2)	0.50399 (8)	0.0203 (6)
H5	0.5977	0.5290	0.5045	0.024*
C6	0.5582 (2)	0.6787 (2)	0.47463 (8)	0.0203 (5)
H6	0.5204	0.6387	0.4549	0.024*
C7	0.52621 (19)	0.9770 (2)	0.43137 (7)	0.0166 (5)
C8	0.4600 (2)	1.0082 (2)	0.39899 (7)	0.0177 (5)
H8	0.4152	0.9485	0.3879	0.021*
C9	0.52583 (19)	1.1984 (2)	0.40114 (7)	0.0164 (5)
C10	0.5304 (2)	1.3140 (2)	0.38633 (7)	0.0198 (5)
H10	0.4862	1.3348	0.3652	0.024*
C11	0.5988 (2)	1.3973 (2)	0.40237 (8)	0.0217 (6)
H11	0.6026	1.4754	0.3922	0.026*
C12	0.6633 (2)	1.3663 (2)	0.43405 (8)	0.0212 (6)
H12	0.7101	1.4243	0.4451	0.025*
C13	0.6594 (2)	1.2541 (2)	0.44907 (8)	0.0205 (6)
H13	0.7028	1.2350	0.4705	0.025*
C14	0.59083 (19)	1.1667 (2)	0.43268 (7)	0.0161 (5)
C15	0.1823 (2)	0.4550 (2)	0.30593 (7)	0.0177 (5)
C16	0.2491 (2)	0.3811 (2)	0.28402 (8)	0.0247 (6)
H16	0.3268	0.3891	0.2850	0.030*
C17	0.2014 (2)	0.2959 (3)	0.26090 (8)	0.0266 (6)
H17	0.2466	0.2452	0.2461	0.032*
C18	0.0884 (2)	0.2845 (2)	0.25939 (8)	0.0224 (6)
C19	0.0212 (2)	0.3556 (2)	0.28118 (7)	0.0191 (5)
H19	−0.0564	0.3466	0.2802	0.023*
C20	0.0680 (2)	0.4399 (2)	0.30451 (7)	0.0189 (5)
H20	0.0221	0.4884	0.3198	0.023*
C21	0.3268 (2)	0.5814 (2)	0.33713 (7)	0.0183 (5)
C22	0.3404 (2)	0.6720 (2)	0.36542 (8)	0.0211 (6)
H22	0.2767	0.7019	0.3778	0.025*
C23	0.5259 (2)	0.6708 (2)	0.35548 (7)	0.0187 (5)
C24	0.6321 (2)	0.7168 (2)	0.36303 (8)	0.0249 (6)
H24	0.6415	0.7777	0.3813	0.030*
C25	0.7212 (2)	0.6729 (3)	0.34385 (8)	0.0286 (7)
H25	0.7925	0.7037	0.3489	0.034*
C26	0.7081 (2)	0.5829 (3)	0.31683 (8)	0.0288 (6)
H26	0.7707	0.5532	0.3038	0.035*
C27	0.6061 (2)	0.5372 (2)	0.30895 (8)	0.0236 (6)
H27	0.5982	0.4760	0.2907	0.028*
C28	0.5127 (2)	0.5815 (2)	0.32813 (7)	0.0193 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0267 (3)	0.0231 (3)	0.0250 (4)	0.0045 (3)	−0.0042 (3)	0.0047 (3)
Cl2	0.0256 (4)	0.0359 (4)	0.0365 (4)	−0.0093 (3)	−0.0007 (3)	−0.0154 (3)
N1	0.0227 (11)	0.0162 (11)	0.0190 (12)	−0.0039 (9)	−0.0045 (9)	0.0001 (9)
N2	0.0150 (10)	0.0171 (11)	0.0180 (11)	0.0003 (8)	0.0001 (8)	0.0008 (9)
N3	0.0160 (10)	0.0170 (11)	0.0197 (11)	−0.0013 (8)	0.0004 (8)	0.0017 (9)
N4	0.0163 (11)	0.0187 (11)	0.0227 (12)	−0.0025 (9)	0.0027 (9)	−0.0045 (9)
N5	0.0187 (11)	0.0217 (11)	0.0192 (11)	−0.0023 (9)	0.0001 (9)	−0.0026 (9)
N6	0.0236 (11)	0.0203 (12)	0.0208 (12)	−0.0024 (9)	−0.0017 (9)	0.0006 (9)
C1	0.0134 (11)	0.0189 (13)	0.0191 (13)	0.0002 (10)	0.0018 (10)	0.0001 (10)
C2	0.0182 (12)	0.0167 (12)	0.0172 (13)	0.0003 (10)	0.0030 (10)	−0.0011 (10)
C3	0.0179 (12)	0.0215 (13)	0.0184 (13)	0.0011 (10)	0.0011 (10)	−0.0013 (11)
C4	0.0163 (12)	0.0221 (13)	0.0202 (14)	0.0031 (10)	0.0012 (10)	0.0029 (11)
C5	0.0189 (12)	0.0138 (12)	0.0283 (15)	−0.0016 (10)	0.0015 (11)	0.0027 (11)
C6	0.0198 (12)	0.0188 (13)	0.0224 (14)	−0.0029 (10)	−0.0019 (10)	0.0006 (11)
C7	0.0145 (11)	0.0172 (12)	0.0181 (13)	0.0014 (9)	0.0021 (10)	0.0007 (10)
C8	0.0157 (12)	0.0192 (13)	0.0181 (13)	−0.0031 (10)	0.0001 (10)	−0.0026 (10)
C9	0.0119 (11)	0.0192 (13)	0.0180 (13)	0.0007 (10)	0.0011 (9)	−0.0014 (10)
C10	0.0190 (12)	0.0200 (13)	0.0204 (14)	0.0037 (11)	−0.0002 (10)	0.0041 (11)
C11	0.0216 (13)	0.0152 (13)	0.0284 (15)	0.0007 (10)	0.0001 (11)	0.0013 (11)
C12	0.0181 (12)	0.0192 (13)	0.0263 (15)	−0.0015 (10)	−0.0014 (11)	−0.0012 (11)
C13	0.0186 (13)	0.0215 (13)	0.0215 (14)	−0.0013 (10)	−0.0015 (10)	−0.0002 (11)
C14	0.0127 (11)	0.0178 (12)	0.0179 (13)	0.0028 (9)	0.0022 (9)	0.0018 (10)
C15	0.0184 (12)	0.0172 (12)	0.0177 (13)	−0.0017 (10)	−0.0008 (10)	0.0009 (10)
C16	0.0170 (13)	0.0268 (15)	0.0305 (16)	−0.0045 (11)	0.0038 (11)	−0.0055 (12)
C17	0.0215 (14)	0.0270 (15)	0.0312 (16)	−0.0006 (11)	0.0026 (12)	−0.0096 (12)
C18	0.0215 (13)	0.0213 (14)	0.0245 (15)	−0.0053 (10)	−0.0031 (11)	0.0002 (11)
C19	0.0151 (12)	0.0198 (13)	0.0223 (14)	−0.0033 (10)	−0.0013 (10)	0.0033 (11)
C20	0.0185 (12)	0.0205 (13)	0.0178 (13)	0.0006 (10)	0.0013 (10)	0.0023 (10)
C21	0.0195 (12)	0.0147 (12)	0.0207 (14)	−0.0036 (10)	−0.0013 (10)	0.0025 (10)
C22	0.0234 (13)	0.0169 (13)	0.0230 (14)	−0.0003 (11)	0.0011 (11)	−0.0003 (11)
C23	0.0210 (12)	0.0157 (12)	0.0195 (13)	−0.0031 (10)	−0.0032 (10)	0.0028 (10)
C24	0.0279 (15)	0.0190 (14)	0.0278 (16)	−0.0048 (11)	−0.0061 (12)	−0.0003 (12)
C25	0.0199 (13)	0.0343 (16)	0.0316 (16)	−0.0071 (12)	−0.0070 (11)	0.0028 (13)
C26	0.0200 (13)	0.0350 (16)	0.0314 (16)	−0.0005 (12)	0.0002 (12)	0.0007 (13)
C27	0.0213 (13)	0.0250 (14)	0.0244 (15)	−0.0018 (11)	0.0003 (11)	−0.0023 (12)
C28	0.0181 (12)	0.0194 (13)	0.0203 (14)	−0.0018 (10)	−0.0022 (10)	0.0026 (11)

Geometric parameters (Å, º) top

Cl1—C4	1.745 (3)	C10—C11	1.375 (4)
Cl2—C18	1.743 (3)	C10—H10	0.9500
N1—C7	1.373 (3)	C11—C12	1.412 (4)
N1—C1	1.406 (3)	C11—H11	0.9500
N1—H1	0.883 (10)	C12—C13	1.369 (4)
N2—C7	1.310 (3)	C12—H12	0.9500
N2—C14	1.374 (3)	C13—C14	1.413 (3)
N3—C8	1.297 (3)	C13—H13	0.9500
N3—C9	1.383 (3)	C15—C16	1.397 (4)
N4—C21	1.368 (3)	C15—C20	1.400 (3)
N4—C15	1.412 (3)	C16—C17	1.387 (4)
N4—H4	0.877 (10)	C16—H16	0.9500
N5—C21	1.314 (3)	C17—C18	1.381 (4)
N5—C28	1.377 (3)	C17—H17	0.9500
N6—C22	1.306 (3)	C18—C19	1.379 (4)
N6—C23	1.380 (3)	C19—C20	1.380 (4)
C1—C2	1.394 (4)	C19—H19	0.9500
C1—C6	1.403 (4)	C20—H20	0.9500
C2—C3	1.394 (4)	C21—C22	1.438 (4)
C2—H2	0.9500	C22—H22	0.9500
C3—C4	1.382 (4)	C23—C28	1.404 (4)
C3—H3	0.9500	C23—C24	1.415 (4)
C4—C5	1.382 (4)	C24—C25	1.371 (4)
C5—C6	1.391 (4)	C24—H24	0.9500
C5—H5	0.9500	C25—C26	1.401 (4)
C6—H6	0.9500	C25—H25	0.9500
C7—C8	1.444 (3)	C26—C27	1.370 (4)
C8—H8	0.9500	C26—H26	0.9500
C9—C10	1.403 (4)	C27—C28	1.413 (4)
C9—C14	1.414 (3)	C27—H27	0.9500

C7—N1—C1	129.7 (2)	C12—C13—H13	120.0
C7—N1—H1	115.4 (19)	C14—C13—H13	120.0
C1—N1—H1	114.2 (19)	N2—C14—C9	122.9 (2)
C7—N2—C14	115.6 (2)	N2—C14—C13	118.5 (2)
C8—N3—C9	116.8 (2)	C9—C14—C13	118.6 (2)
C21—N4—C15	129.5 (2)	C16—C15—C20	119.0 (2)
C21—N4—H4	115 (2)	C16—C15—N4	124.9 (2)
C15—N4—H4	116 (2)	C20—C15—N4	116.2 (2)
C21—N5—C28	115.9 (2)	C17—C16—C15	119.7 (2)
C22—N6—C23	116.4 (2)	C17—C16—H16	120.1
C2—C1—C6	119.1 (2)	C15—C16—H16	120.1
C2—C1—N1	124.4 (2)	C18—C17—C16	120.2 (3)
C6—C1—N1	116.4 (2)	C18—C17—H17	119.9
C1—C2—C3	119.8 (2)	C16—C17—H17	119.9
C1—C2—H2	120.1	C19—C18—C17	120.9 (3)
C3—C2—H2	120.1	C19—C18—Cl2	118.9 (2)
C4—C3—C2	120.2 (2)	C17—C18—Cl2	120.1 (2)
C4—C3—H3	119.9	C18—C19—C20	119.3 (2)
C2—C3—H3	119.9	C18—C19—H19	120.4
C3—C4—C5	121.0 (2)	C20—C19—H19	120.4
C3—C4—Cl1	119.7 (2)	C19—C20—C15	120.9 (2)
C5—C4—Cl1	119.3 (2)	C19—C20—H20	119.5
C4—C5—C6	119.1 (2)	C15—C20—H20	119.5
C4—C5—H5	120.4	N5—C21—N4	121.9 (2)
C6—C5—H5	120.4	N5—C21—C22	121.9 (2)
C5—C6—C1	120.8 (2)	N4—C21—C22	116.2 (2)
C5—C6—H6	119.6	N6—C22—C21	122.9 (2)
C1—C6—H6	119.6	N6—C22—H22	118.6
N2—C7—N1	122.9 (2)	C21—C22—H22	118.6
N2—C7—C8	122.0 (2)	N6—C23—C28	120.7 (2)
N1—C7—C8	115.2 (2)	N6—C23—C24	119.6 (2)
N3—C8—C7	123.0 (2)	C28—C23—C24	119.7 (2)
N3—C8—H8	118.5	C25—C24—C23	119.7 (3)
C7—C8—H8	118.5	C25—C24—H24	120.1
N3—C9—C10	119.8 (2)	C23—C24—H24	120.1
N3—C9—C14	119.7 (2)	C24—C25—C26	120.5 (3)
C10—C9—C14	120.5 (2)	C24—C25—H25	119.7
C11—C10—C9	120.0 (2)	C26—C25—H25	119.7
C11—C10—H10	120.0	C27—C26—C25	120.8 (3)
C9—C10—H10	120.0	C27—C26—H26	119.6
C10—C11—C12	119.7 (2)	C25—C26—H26	119.6
C10—C11—H11	120.1	C26—C27—C28	119.8 (3)
C12—C11—H11	120.1	C26—C27—H27	120.1
C13—C12—C11	121.1 (2)	C28—C27—H27	120.1
C13—C12—H12	119.4	N5—C28—C23	122.2 (2)
C11—C12—H12	119.4	N5—C28—C27	118.4 (2)
C12—C13—C14	120.0 (2)	C23—C28—C27	119.4 (2)

C7—N1—C1—C2	12.7 (4)	C21—N4—C15—C16	2.0 (4)
C7—N1—C1—C6	−167.7 (3)	C21—N4—C15—C20	−178.8 (3)
C6—C1—C2—C3	−0.3 (4)	C20—C15—C16—C17	1.1 (4)
N1—C1—C2—C3	179.3 (2)	N4—C15—C16—C17	−179.7 (3)
C1—C2—C3—C4	−0.1 (4)	C15—C16—C17—C18	0.3 (4)
C2—C3—C4—C5	0.2 (4)	C16—C17—C18—C19	−1.2 (4)
C2—C3—C4—Cl1	−179.64 (19)	C16—C17—C18—Cl2	177.8 (2)
C3—C4—C5—C6	0.0 (4)	C17—C18—C19—C20	0.6 (4)
Cl1—C4—C5—C6	179.86 (19)	Cl2—C18—C19—C20	−178.3 (2)
C4—C5—C6—C1	−0.4 (4)	C18—C19—C20—C15	0.8 (4)
C2—C1—C6—C5	0.5 (4)	C16—C15—C20—C19	−1.6 (4)
N1—C1—C6—C5	−179.1 (2)	N4—C15—C20—C19	179.1 (2)
C14—N2—C7—N1	−179.6 (2)	C28—N5—C21—N4	178.5 (2)
C14—N2—C7—C8	0.6 (3)	C28—N5—C21—C22	−2.7 (4)
C1—N1—C7—N2	1.3 (4)	C15—N4—C21—N5	2.2 (4)
C1—N1—C7—C8	−178.8 (2)	C15—N4—C21—C22	−176.7 (2)
C9—N3—C8—C7	0.5 (4)	C23—N6—C22—C21	1.6 (4)
N2—C7—C8—N3	−0.8 (4)	N5—C21—C22—N6	1.0 (4)
N1—C7—C8—N3	179.4 (2)	N4—C21—C22—N6	179.8 (2)
C8—N3—C9—C10	178.7 (2)	C22—N6—C23—C28	−2.2 (4)
C8—N3—C9—C14	0.0 (3)	C22—N6—C23—C24	177.3 (2)
N3—C9—C10—C11	−178.5 (2)	N6—C23—C24—C25	179.9 (3)
C14—C9—C10—C11	0.3 (4)	C28—C23—C24—C25	−0.6 (4)
C9—C10—C11—C12	−0.8 (4)	C23—C24—C25—C26	0.0 (4)
C10—C11—C12—C13	0.3 (4)	C24—C25—C26—C27	0.2 (4)
C11—C12—C13—C14	0.6 (4)	C25—C26—C27—C28	0.3 (4)
C7—N2—C14—C9	−0.2 (3)	C21—N5—C28—C23	2.1 (4)
C7—N2—C14—C13	−179.6 (2)	C21—N5—C28—C27	−178.1 (2)
N3—C9—C14—N2	−0.1 (4)	N6—C23—C28—N5	0.4 (4)
C10—C9—C14—N2	−178.9 (2)	C24—C23—C28—N5	−179.1 (2)
N3—C9—C14—C13	179.3 (2)	N6—C23—C28—C27	−179.4 (2)
C10—C9—C14—C13	0.6 (4)	C24—C23—C28—C27	1.1 (4)
C12—C13—C14—N2	178.5 (2)	C26—C27—C28—N5	179.3 (3)
C12—C13—C14—C9	−1.0 (4)	C26—C27—C28—C23	−0.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N6	0.88 (1)	2.24 (1)	3.086 (3)	160 (3)
N4—H4···N3ⁱ	0.88 (1)	2.19 (2)	3.010 (3)	155 (3)

Symmetry code: (i) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀ClN₃
M_r	255.70
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	12.155 (1), 11.238 (1), 35.421 (3)
V (Å³)	4838.3 (8)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.916, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	25622, 5495, 4111
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.135, 1.07
No. of reflections	5495
No. of parameters	331
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N6	0.88 (1)	2.24 (1)	3.086 (3)	160 (3)
N4—H4···N3ⁱ	0.88 (1)	2.19 (2)	3.010 (3)	155 (3)

Symmetry code: (i) −x+1/2, y−1/2, z.

Acknowledgements

We thank the University of Malaya for supporting this study (grant No. FS 302/2007 C, FS 313/2007 C, FP 067/2006 A).

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fairuz, M. Z. A., Aiyub, Z., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o1800. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttigen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar