3-Chloro-6-[2-(cyclo­pentyl­idene)hydrazin-1-yl]pyridazine

Ather, A.Q.; Tahir, M.N.; Khan, M.A.; Athar, M.M.

doi:10.1107/S1600536811011342

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o1020

doi:10.1107/S1600536811011342

Open

access

3-Chloro-6-[2-(cyclopentylidene)hydrazin-1-yl]pyridazine

Abdul Qayyum Ather,^a,^b M. Nawaz Tahir,^c ^* Misbahul Ain Khan ^a and Muhammad Makshoof Athar ^d

^aDepartment of Chemistry, Islamia University, Bahawalpur, Pakistan, ^bApplied Chemistry Research Center, PCSIR Laboratories Complex, Lahore 54600, Pakistan, ^cDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^dInstitute of Chemistry, University of the Punjab, Lahore, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 20 March 2011; accepted 27 March 2011; online 31 March 2011)

The asymmetric unit of the title compound, C₉H₁₁ClN₄, contains two virtually planar molecules that differ in conformation about the bond connecting the hydrazine and pyridazine units. The 3-chloro-6-hydrazinylpyridazine and cyclopentane groups are oriented at dihedral angles of 4.5 (3) and 8.8 (4)° in the two molecules. In the crystal, the molecules form a one dimensional polymeric structure extending along the a axis via N—H⋯N hydrogen bonds. The crystal stucired was an inversion twin [ratio of the twin domains = 0.73 (9):0.27 (9)].

Related literature

For related structures, see: Ather et al. (2010a ,b ,c ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₉H₁₁ClN₄
M_r = 210.67
Orthorhombic, P c a 2₁
a = 10.180 (5) Å
b = 9.870 (5) Å
c = 20.049 (3) Å
V = 2014.5 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 296 K
0.30 × 0.15 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.942, T_max = 0.950
7740 measured reflections
3355 independent reflections
2130 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.120
S = 1.00
3355 reflections
254 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ), 1307 Friedel pairs
Flack parameter: 0.73 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N5ⁱ	0.86	2.52	3.295 (5)	150
N3—H3A⋯N6ⁱ	0.86	2.27	3.088 (5)	159
N7—H7⋯N1ⁱⁱ	0.86	2.19	3.041 (5)	170
Symmetry codes: (i) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011342/gk2360sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011342/gk2360Isup2.hkl

checkCIF report

Comment top

In continuation to on our studies on 3-chloro-6-hydrazinylpyridazine derivatives (Ather et al., 2010a,b,c), the title compound (Fig. 1) is being reported here.

There are two symmetry independent molecule in the asymmetric unit of title compound that differ in conformation. In one molecule 3-chloro-6-hydrazinylpyridazine moiety A (C1—C4/N1—N4/CL1) and cyclopentane group B (C5–C9) are planar with r. m. s. deviations of 0.0104 and 0.0354 Å. The dihedral angle between A/B is 8.5 (4)°. In the second symmetry independent molecule 3-chloro-6-hydrazinylpyridazine moiety C (C10—C13/N5—N8/CL2) and cyclopentane gruop D (C14–C18) are also planar with r. m. s. deviations of 0.0068 and 0.0046 Å. The dihedral angle between C/D is 4.5 (3)°. The title compound consists of one dimensional polymeric chains via N–H···N hydrogen bonds extending along the crystallographic a-axis (Table 1, Fig. 2).

Related literature top

For related structures, see: Ather et al. (2010a,b,c). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

3-Chloro-6-hydrazinylpyridazine (0.5 g, 3.46 mmol), dissolved in ethanol (10 ml) and refluxed for 15 min. Cyclopentanone (0.291 g, 3.459 mmol) was added to the formar solution and refluxed about 3 h, till the completion of reaction monitored through TLC. On completion of the reaction mixture was concenterated under vacuum. The crude product was recrystallized in ethanol which yielded the light yellow needles of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The partial packing diagram (PLATON; Spek, 2009) showing polymeric chains extending along the a-axis. The H-atoms of cyclopentane are omitted for clarity.

3-Chloro-6-{2-[cyclopentylidene]hydrazin-1-yl}pyridazine top

Crystal data top

C₉H₁₁ClN₄	F(000) = 880
M_r = 210.67	D_x = 1.389 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1374 reflections
a = 10.180 (5) Å	θ = 2.9–28.3°
b = 9.870 (5) Å	µ = 0.34 mm⁻¹
c = 20.049 (3) Å	T = 296 K
V = 2014.5 (15) Å³	Needle, light yellow
Z = 8	0.30 × 0.15 × 0.14 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3355 independent reflections
Radiation source: fine-focus sealed tube	2130 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 7.60 pixels mm^-1	θ_max = 26.0°, θ_min = 2.9°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→11
T_min = 0.942, T_max = 0.950	l = −24→19
7740 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.053P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3355 reflections	Δρ_max = 0.18 e Å⁻³
254 parameters	Δρ_min = −0.17 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1307 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.73 (9)

Crystal data top

C₉H₁₁ClN₄	V = 2014.5 (15) Å³
M_r = 210.67	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 10.180 (5) Å	µ = 0.34 mm⁻¹
b = 9.870 (5) Å	T = 296 K
c = 20.049 (3) Å	0.30 × 0.15 × 0.14 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3355 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2130 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.950	R_int = 0.044
7740 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.120	Δρ_max = 0.18 e Å⁻³
S = 1.00	Δρ_min = −0.17 e Å⁻³
3355 reflections	Absolute structure: Flack (1983), 1307 Friedel pairs
254 parameters	Absolute structure parameter: 0.73 (9)
1 restraint

Special details top

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 > 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	0.05268 (12)	−0.05719 (13)	0.64742 (7)	0.0730 (4)
N1	0.2266 (4)	−0.1211 (3)	0.5585 (2)	0.0563 (10)
N2	0.3221 (4)	−0.1007 (3)	0.5124 (2)	0.0540 (10)
N3	0.4576 (4)	0.0479 (3)	0.4564 (2)	0.0564 (10)
H3A	0.4848	0.1290	0.4488	0.068*
N4	0.5125 (4)	−0.0589 (3)	0.4229 (2)	0.0576 (10)
C1	0.3608 (4)	0.0263 (4)	0.5012 (2)	0.0403 (10)
C2	0.3031 (4)	0.1383 (4)	0.5338 (2)	0.0495 (11)
H2	0.3302	0.2261	0.5240	0.059*
C3	0.2085 (4)	0.1165 (4)	0.5791 (2)	0.0489 (12)
H3	0.1686	0.1871	0.6022	0.059*
C4	0.1736 (4)	−0.0193 (4)	0.5896 (2)	0.0490 (12)
C5	0.5972 (5)	−0.0292 (4)	0.3777 (3)	0.0553 (12)
C6	0.6610 (5)	−0.1391 (5)	0.3385 (3)	0.0860 (17)
H6A	0.7147	−0.1958	0.3671	0.103*
H6B	0.5955	−0.1954	0.3169	0.103*
C7	0.7435 (8)	−0.0690 (6)	0.2881 (4)	0.112 (3)
H7A	0.8349	−0.0934	0.2945	0.134*
H7B	0.7175	−0.0972	0.2436	0.134*
C8	0.7283 (7)	0.0760 (6)	0.2945 (4)	0.101 (2)
H8A	0.6859	0.1125	0.2551	0.121*
H8B	0.8137	0.1187	0.2991	0.121*
C9	0.6450 (4)	0.1042 (4)	0.3559 (2)	0.0574 (12)
H9A	0.6972	0.1466	0.3906	0.069*
H9B	0.5720	0.1634	0.3449	0.069*
Cl2	0.72267 (11)	0.48307 (11)	−0.15057 (7)	0.0678 (4)
N5	0.5643 (3)	0.6264 (3)	−0.07810 (19)	0.0544 (10)
N6	0.4710 (3)	0.6489 (3)	−0.03214 (19)	0.0512 (9)
N7	0.3193 (3)	0.5761 (3)	0.04280 (19)	0.0527 (10)
H7	0.2969	0.6590	0.0495	0.063*
N8	0.2597 (4)	0.4729 (3)	0.0777 (2)	0.0555 (11)
C10	0.4144 (4)	0.5451 (4)	−0.0025 (2)	0.0444 (11)
C11	0.4524 (4)	0.4099 (4)	−0.0162 (2)	0.0471 (11)
H11	0.4124	0.3377	0.0057	0.056*
C12	0.5459 (4)	0.3885 (4)	−0.0607 (2)	0.0466 (11)
H12	0.5744	0.3014	−0.0710	0.056*
C13	0.6001 (4)	0.5023 (4)	−0.0916 (2)	0.0464 (11)
C14	0.1787 (4)	0.5052 (4)	0.1230 (3)	0.0533 (12)
C15	0.1343 (4)	0.6416 (4)	0.1458 (3)	0.0658 (12)
H15A	0.0928	0.6908	0.1096	0.079*
H15B	0.2080	0.6943	0.1622	0.079*
C16	0.0371 (6)	0.6142 (7)	0.2012 (3)	0.105 (2)
H16A	0.0666	0.6569	0.2421	0.125*
H16B	−0.0480	0.6515	0.1896	0.125*
C17	0.0264 (7)	0.4674 (7)	0.2109 (4)	0.095 (2)
H17A	0.0509	0.4442	0.2562	0.114*
H17B	−0.0637	0.4389	0.2038	0.114*
C18	0.1122 (5)	0.3979 (5)	0.1643 (3)	0.0870 (19)
H18A	0.0617	0.3377	0.1359	0.104*
H18B	0.1770	0.3446	0.1882	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0700 (7)	0.0779 (9)	0.0711 (9)	−0.0235 (6)	0.0072 (8)	0.0036 (8)
N1	0.068 (3)	0.0344 (19)	0.067 (3)	−0.0143 (19)	0.000 (2)	−0.0021 (19)
N2	0.069 (2)	0.0250 (17)	0.068 (3)	−0.0104 (17)	−0.008 (2)	−0.0068 (17)
N3	0.077 (3)	0.0236 (18)	0.068 (3)	−0.0011 (16)	0.011 (2)	−0.0014 (18)
N4	0.070 (3)	0.034 (2)	0.068 (3)	0.0026 (17)	0.005 (2)	−0.0077 (19)
C1	0.050 (3)	0.029 (2)	0.042 (3)	−0.0022 (17)	−0.005 (2)	−0.0016 (18)
C2	0.065 (3)	0.026 (2)	0.057 (3)	0.000 (2)	0.003 (3)	0.0006 (19)
C3	0.057 (3)	0.032 (2)	0.058 (3)	0.005 (2)	−0.006 (3)	−0.0003 (19)
C4	0.050 (3)	0.046 (3)	0.052 (3)	−0.014 (2)	−0.010 (2)	0.005 (2)
C5	0.065 (3)	0.039 (3)	0.062 (3)	0.008 (2)	0.003 (3)	−0.002 (2)
C6	0.100 (4)	0.048 (3)	0.110 (5)	0.008 (3)	0.035 (4)	−0.016 (3)
C7	0.149 (7)	0.072 (4)	0.114 (6)	0.012 (4)	0.069 (5)	−0.006 (4)
C8	0.117 (6)	0.069 (4)	0.119 (6)	0.008 (3)	0.056 (5)	0.010 (4)
C9	0.069 (3)	0.051 (3)	0.053 (3)	−0.003 (2)	0.007 (3)	0.000 (2)
Cl2	0.0699 (7)	0.0664 (8)	0.0672 (8)	−0.0042 (6)	0.0083 (7)	−0.0049 (7)
N5	0.066 (3)	0.035 (2)	0.063 (3)	−0.0066 (17)	−0.002 (2)	0.0023 (17)
N6	0.061 (2)	0.0271 (18)	0.066 (2)	−0.0021 (16)	0.001 (2)	−0.0045 (17)
N7	0.061 (2)	0.0283 (18)	0.069 (3)	0.0018 (17)	0.006 (2)	−0.0037 (18)
N8	0.063 (2)	0.033 (2)	0.070 (3)	−0.0065 (18)	0.010 (2)	0.0003 (18)
C10	0.053 (3)	0.028 (2)	0.052 (3)	0.0021 (18)	−0.005 (2)	−0.001 (2)
C11	0.055 (3)	0.025 (2)	0.062 (3)	−0.0033 (18)	0.001 (3)	0.003 (2)
C12	0.055 (3)	0.026 (2)	0.058 (3)	−0.0014 (19)	−0.004 (3)	−0.0035 (19)
C13	0.052 (2)	0.039 (2)	0.048 (3)	−0.002 (2)	−0.008 (2)	−0.002 (2)
C14	0.056 (3)	0.045 (3)	0.059 (3)	−0.001 (2)	0.002 (3)	−0.004 (2)
C15	0.071 (3)	0.056 (3)	0.071 (3)	0.005 (2)	0.001 (3)	−0.015 (3)
C16	0.121 (5)	0.075 (5)	0.117 (6)	0.010 (4)	0.041 (5)	−0.012 (4)
C17	0.108 (5)	0.097 (5)	0.079 (5)	0.003 (4)	0.017 (4)	−0.008 (4)
C18	0.105 (4)	0.057 (3)	0.098 (5)	−0.006 (3)	0.044 (4)	0.006 (3)

Geometric parameters (Å, º) top

Cl1—C4	1.732 (5)	Cl2—C13	1.730 (5)
N1—C4	1.299 (5)	N5—C13	1.306 (5)
N1—N2	1.357 (5)	N5—N6	1.342 (5)
N2—C1	1.333 (5)	N6—C10	1.317 (5)
N3—C1	1.351 (5)	N7—C10	1.362 (5)
N3—N4	1.370 (5)	N7—N8	1.377 (5)
N3—H3A	0.8600	N7—H7	0.8600
N4—C5	1.285 (6)	N8—C14	1.268 (5)
C1—C2	1.413 (5)	C10—C11	1.416 (5)
C2—C3	1.341 (6)	C11—C12	1.322 (6)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.402 (6)	C12—C13	1.397 (6)
C3—H3	0.9300	C12—H12	0.9300
C5—C9	1.470 (6)	C14—C15	1.492 (6)
C5—C6	1.489 (6)	C14—C18	1.504 (7)
C6—C7	1.485 (8)	C15—C16	1.511 (7)
C6—H6A	0.9700	C15—H15A	0.9700
C6—H6B	0.9700	C15—H15B	0.9700
C7—C8	1.445 (7)	C16—C17	1.466 (9)
C7—H7A	0.9700	C16—H16A	0.9700
C7—H7B	0.9700	C16—H16B	0.9700
C8—C9	1.522 (8)	C17—C18	1.452 (8)
C8—H8A	0.9700	C17—H17A	0.9700
C8—H8B	0.9700	C17—H17B	0.9700
C9—H9A	0.9700	C18—H18A	0.9700
C9—H9B	0.9700	C18—H18B	0.9700

C4—N1—N2	120.7 (4)	C13—N5—N6	119.6 (3)
C1—N2—N1	117.7 (3)	C10—N6—N5	119.4 (3)
C1—N3—N4	120.1 (3)	C10—N7—N8	119.1 (3)
C1—N3—H3A	119.9	C10—N7—H7	120.5
N4—N3—H3A	119.9	N8—N7—H7	120.5
C5—N4—N3	116.3 (4)	C14—N8—N7	117.7 (4)
N2—C1—N3	118.4 (3)	N6—C10—N7	115.9 (4)
N2—C1—C2	122.4 (4)	N6—C10—C11	121.7 (4)
N3—C1—C2	119.2 (4)	N7—C10—C11	122.3 (4)
C3—C2—C1	119.1 (4)	C12—C11—C10	118.6 (4)
C3—C2—H2	120.5	C12—C11—H11	120.7
C1—C2—H2	120.5	C10—C11—H11	120.7
C2—C3—C4	115.9 (4)	C11—C12—C13	117.1 (4)
C2—C3—H3	122.0	C11—C12—H12	121.5
C4—C3—H3	122.0	C13—C12—H12	121.5
N1—C4—C3	124.2 (4)	N5—C13—C12	123.5 (4)
N1—C4—Cl1	116.7 (3)	N5—C13—Cl2	116.5 (3)
C3—C4—Cl1	119.1 (4)	C12—C13—Cl2	120.0 (3)
N4—C5—C9	129.5 (4)	N8—C14—C15	130.1 (4)
N4—C5—C6	119.9 (4)	N8—C14—C18	120.6 (4)
C9—C5—C6	110.6 (4)	C15—C14—C18	109.3 (4)
C7—C6—C5	105.4 (4)	C14—C15—C16	105.2 (4)
C7—C6—H6A	110.7	C14—C15—H15A	110.7
C5—C6—H6A	110.7	C16—C15—H15A	110.7
C7—C6—H6B	110.7	C14—C15—H15B	110.7
C5—C6—H6B	110.7	C16—C15—H15B	110.7
H6A—C6—H6B	108.8	H15A—C15—H15B	108.8
C8—C7—C6	109.9 (5)	C17—C16—C15	108.9 (5)
C8—C7—H7A	109.7	C17—C16—H16A	109.9
C6—C7—H7A	109.7	C15—C16—H16A	109.9
C8—C7—H7B	109.7	C17—C16—H16B	109.9
C6—C7—H7B	109.7	C15—C16—H16B	109.9
H7A—C7—H7B	108.2	H16A—C16—H16B	108.3
C7—C8—C9	108.2 (5)	C18—C17—C16	109.7 (5)
C7—C8—H8A	110.1	C18—C17—H17A	109.7
C9—C8—H8A	110.1	C16—C17—H17A	109.7
C7—C8—H8B	110.1	C18—C17—H17B	109.7
C9—C8—H8B	110.1	C16—C17—H17B	109.7
H8A—C8—H8B	108.4	H17A—C17—H17B	108.2
C5—C9—C8	105.1 (4)	C17—C18—C14	107.0 (5)
C5—C9—H9A	110.7	C17—C18—H18A	110.3
C8—C9—H9A	110.7	C14—C18—H18A	110.3
C5—C9—H9B	110.7	C17—C18—H18B	110.3
C8—C9—H9B	110.7	C14—C18—H18B	110.3
H9A—C9—H9B	108.8	H18A—C18—H18B	108.6

C4—N1—N2—C1	1.3 (6)	C13—N5—N6—C10	−1.8 (6)
C1—N3—N4—C5	175.2 (4)	C10—N7—N8—C14	174.9 (4)
N1—N2—C1—N3	178.8 (4)	N5—N6—C10—N7	−179.1 (3)
N1—N2—C1—C2	−2.2 (6)	N5—N6—C10—C11	2.2 (6)
N4—N3—C1—N2	0.8 (6)	N8—N7—C10—N6	−177.4 (4)
N4—N3—C1—C2	−178.2 (4)	N8—N7—C10—C11	1.4 (6)
N2—C1—C2—C3	2.1 (6)	N6—C10—C11—C12	−1.0 (6)
N3—C1—C2—C3	−178.9 (4)	N7—C10—C11—C12	−179.7 (4)
C1—C2—C3—C4	−0.9 (6)	C10—C11—C12—C13	−0.4 (6)
N2—N1—C4—C3	−0.1 (6)	N6—N5—C13—C12	0.2 (6)
N2—N1—C4—Cl1	−180.0 (3)	N6—N5—C13—Cl2	−179.1 (3)
C2—C3—C4—N1	0.0 (6)	C11—C12—C13—N5	0.9 (6)
C2—C3—C4—Cl1	179.8 (3)	C11—C12—C13—Cl2	−179.8 (3)
N3—N4—C5—C9	−0.2 (7)	N7—N8—C14—C15	0.4 (7)
N3—N4—C5—C6	−179.5 (4)	N7—N8—C14—C18	−178.5 (4)
N4—C5—C6—C7	175.6 (6)	N8—C14—C15—C16	179.9 (5)
C9—C5—C6—C7	−3.9 (7)	C18—C14—C15—C16	−1.1 (6)
C5—C6—C7—C8	−1.7 (8)	C14—C15—C16—C17	0.7 (6)
C6—C7—C8—C9	6.3 (9)	C15—C16—C17—C18	0.0 (8)
N4—C5—C9—C8	−171.9 (6)	C16—C17—C18—C14	−0.6 (7)
C6—C5—C9—C8	7.5 (6)	N8—C14—C18—C17	−179.8 (5)
C7—C8—C9—C5	−8.4 (7)	C15—C14—C18—C17	1.1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N5ⁱ	0.93	2.73	3.500 (6)	141
N3—H3A···N5ⁱ	0.86	2.52	3.295 (5)	150
N3—H3A···N6ⁱ	0.86	2.27	3.088 (5)	159
N7—H7···N1ⁱⁱ	0.86	2.19	3.041 (5)	170
C12—H12···N4ⁱⁱⁱ	0.93	2.55	3.323 (5)	140

Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) −x+1/2, y+1, z−1/2; (iii) −x+1, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₉H₁₁ClN₄
M_r	210.67
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	296
a, b, c (Å)	10.180 (5), 9.870 (5), 20.049 (3)
V (Å³)	2014.5 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.30 × 0.15 × 0.14

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.942, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	7740, 3355, 2130
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.120, 1.00
No. of reflections	3355
No. of parameters	254
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.17
Absolute structure	Flack (1983), 1307 Friedel pairs
Absolute structure parameter	0.73 (9)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N5ⁱ	0.86	2.52	3.295 (5)	150
N3—H3A···N6ⁱ	0.86	2.27	3.088 (5)	159
N7—H7···N1ⁱⁱ	0.86	2.19	3.041 (5)	170

Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) −x+1/2, y+1, z−1/2.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Bana International, Karachi, Pakistan.

References

Ather, A. Q., Tahir, M. N., Khan, M. A. & Athar, M. M. (2010a). Acta Cryst. E66, o2107. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ather, A. Q., Tahir, M. N., Khan, M. A. & Athar, M. M. (2010b). Acta Cryst. E66, o2441. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ather, A. Q., Tahir, M. N., Khan, M. A. & Athar, M. M. (2010c). Acta Cryst. E66, o2499. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals 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