6-Chloro-N-(2-meth­oxy­phen­yl)pyridazin-3-amine

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

doi:10.1107/S1600536812001535

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o438-o439

doi:10.1107/S1600536812001535

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6-Chloro-N-(2-methoxyphenyl)pyridazin-3-amine

Abdul Qayyum Ather,^a,^b M. Nawaz Tahir,^c ^* Muhammad Naeem Khan,^b 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, ^cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ^dInstitute of Chemistry, University of the Punjab, Lahore, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 7 January 2012; accepted 13 January 2012; online 18 January 2012)

The asymmetric unit of the title compound, C₁₁H₁₀ClN₃O, contains two geometrically different molecules, A and B, in both of which the pyridazine rings are essentially planar with r.m.s. deviations of 0.0137 and 0.0056Å, respectively. In molecule A, the dihedral angle between the pyridazine and benzene rings is 6.5 (2)°, whereas in molecule B it is 27.93 (7)°. In molecule B, an intramolecular N—H⋯O hydrogen bond forms an S(5) ring motif. In both molecules, S(6) ring motifs are present due to non-classical C—H⋯N hydrogen bonds. The π–π interactions between the pyridazine rings of A molecules [3.4740 (13) Å] and B molecules [3.4786 (17) Å] have very similar centroid–centroid separations. π–π Interactions also occur between the benzene rings of B molecules with a centroid–centroid separation of 3.676 (2) Å and a slippage of 1.02 Å. In the crystal, the molecules are linked into chains extending along [010] by C—H⋯N and C—H⋯Cl interactions.

Related literature

For general background and related structures, see: Ather et al. (2010a ,b ,c ; 2011 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₁H₁₀ClN₃O
M_r = 235.67
Monoclinic, P 2/c
a = 14.6018 (5) Å
b = 10.8574 (3) Å
c = 17.4630 (6) Å
β = 126.438 (2)°
V = 2227.29 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 295 K
0.32 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.938, T_max = 0.957
17904 measured reflections
4387 independent reflections
2815 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.110
S = 1.03
4387 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1	0.86	2.14	2.579 (3)	111
N3—H3⋯N4	0.86	2.48	3.278 (2)	155
N6—H6A⋯N1ⁱ	0.86	2.44	3.270 (3)	161
C2—H2⋯Cl2ⁱⁱ	0.93	2.79	3.526 (2)	137
C3—H3A⋯N5	0.93	2.61	3.503 (3)	161
C6—H6⋯N2	0.93	2.31	2.913 (4)	122
C17—H17⋯N5	0.93	2.50	2.992 (3)	113
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

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 (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/S1600536812001535/rk2330sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001535/rk2330Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812001535/rk2330Isup3.cml

checkCIF report

Comment top

In continuation to 6-chloropyridazin derivatives (Ather et al., 2010a,b,c; 2011), the title compound I (Fig. 1) is being reported here.

The two molecules in the asymmetric unit are present, which differ from each other geometrically. In one molecule, the pyridazin ring A (C1-C4/N1/N2) and the phenyl ring B (C5-C10) are planar with r. m. s. deviation of 0.0137Å and 0.0065Å, respectively. The dihedral angle between A/B is 6.5 (2)°. In second molecule, the pyridazin ring C (C12-C15/N4/N5) and the phenyl ring D (C16-C21) are planar with r. m. s. deviation of 0.0056 and 0.0053Å, respectively and the dihedral angle between C/D is 27.93 (7)°. In the more planar molecule, there exists classical intramolecular H-bonding of N–H···O type (Table 1, Fig. 2) with S(5) ring motif (Bernstein et al., 1995). In both molecules S(6) ring motifs are formed due to non-classical C–H···N type of H-bondings (Table 1, Fig. 2). The molecules are interlinked due to the H-bondings of C–H···N and C–H···Cl types (Table 1, Fig. 2) to form the one dimensional polymeric chains extending along [0 1 0]. There exist π–π interactions between the centroids of a phenyl and two pyridazin rings with CgA···CgAⁱ = 3.4740 (13)Å, CgC···CgCⁱ = 3.4786 (17)Å and CgD···CgDⁱⁱ = 3.676 (2)Å (slippage = 1.021Å), where CgA, CgC and CgD are the centroids of the rings A, C and D, respectively. Symmetry codes: (i) 1-x, y, 1/2-z; (ii) -x, 1-y, -z.

Related literature top

For general background and related structures, see: Ather et al. (2010a,b,c; 2011). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

An equimolar quantity (6.71 mmol) of 3,6-dichloropyradizine and 2-methoxyaniline in 10 ml of ethanol was heated under reflux for 3 h. The reaction mixture was concentrated under reduced pressure, cooled and poured over 50 ml of distilled water. The precipitate was filtered and dried in oven on 333 K. The dried crude product was recrystallized in ethanol to obtain colourless needles of I.

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 (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 displacement ellipsoids are drawn at the 30% probability level. The H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Packing diagram of the title compound showing that molecules form one dimensional polymeric chains along [0 1 0].

6-Chloro-N-(2-methoxyphenyl)pyridazin-3-amine top

Crystal data top

C₁₁H₁₀ClN₃O	F(000) = 976
M_r = 235.67	D_x = 1.406 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 773 reflections
a = 14.6018 (5) Å	θ = 2.4–25.3°
b = 10.8574 (3) Å	µ = 0.32 mm⁻¹
c = 17.4630 (6) Å	T = 295 K
β = 126.438 (2)°	Needle, colourless
V = 2227.29 (14) Å³	0.32 × 0.16 × 0.14 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	4387 independent reflections
Radiation source: fine-focus sealed tube	2815 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 8.0 pixels mm^-1	θ_max = 26.0°, θ_min = 1.9°
ω scans	h = −17→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→12
T_min = 0.938, T_max = 0.957	l = −21→21
17904 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.048P)² + 0.3696P] where P = (F_o² + 2F_c²)/3
4387 reflections	(Δ/σ)_max < 0.001
291 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₁H₁₀ClN₃O	V = 2227.29 (14) Å³
M_r = 235.67	Z = 8
Monoclinic, P2/c	Mo Kα radiation
a = 14.6018 (5) Å	µ = 0.32 mm⁻¹
b = 10.8574 (3) Å	T = 295 K
c = 17.4630 (6) Å	0.32 × 0.16 × 0.14 mm
β = 126.438 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4387 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2815 reflections with I > 2σ(I)
T_min = 0.938, T_max = 0.957	R_int = 0.027
17904 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
4387 reflections	Δρ_min = −0.21 e Å⁻³
291 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.46850 (6)	−0.13866 (5)	0.05144 (5)	0.0738 (2)
O1	0.24223 (15)	0.23518 (15)	0.32088 (12)	0.0808 (7)
N1	0.36545 (16)	−0.13820 (14)	0.13098 (13)	0.0619 (6)
N2	0.32177 (15)	−0.08784 (14)	0.17449 (13)	0.0607 (7)
N3	0.28781 (15)	0.08591 (15)	0.23280 (13)	0.0659 (7)
C1	0.40898 (17)	−0.06681 (16)	0.10082 (14)	0.0523 (7)
C2	0.41035 (19)	0.06066 (17)	0.10578 (15)	0.0626 (8)
C3	0.3676 (2)	0.11179 (16)	0.14842 (16)	0.0645 (9)
C4	0.32520 (17)	0.03400 (16)	0.18478 (14)	0.0528 (7)
C5	0.23884 (17)	0.0334 (2)	0.27383 (15)	0.0622 (8)
C6	0.2125 (2)	−0.0903 (2)	0.26998 (19)	0.0792 (10)
C7	0.1651 (3)	−0.1314 (3)	0.3150 (2)	0.1053 (16)
C8	0.1428 (3)	−0.0507 (3)	0.3617 (2)	0.1073 (14)
C9	0.1660 (2)	0.0735 (3)	0.36443 (19)	0.0881 (11)
C10	0.21385 (19)	0.1147 (2)	0.32131 (16)	0.0673 (9)
C11	0.2238 (3)	0.3246 (3)	0.3706 (2)	0.0938 (11)
Cl2	0.56300 (6)	0.35556 (5)	0.46367 (4)	0.0777 (2)
O2	0.08261 (14)	0.73892 (13)	−0.00138 (12)	0.0856 (7)
N4	0.40277 (16)	0.36064 (13)	0.28154 (14)	0.0582 (7)
N5	0.32848 (15)	0.41352 (13)	0.19496 (13)	0.0575 (6)
N6	0.25123 (16)	0.59100 (15)	0.10279 (14)	0.0722 (7)
C12	0.47012 (18)	0.42988 (16)	0.35550 (15)	0.0537 (7)
C13	0.47274 (19)	0.55815 (17)	0.35300 (17)	0.0622 (8)
C14	0.3991 (2)	0.61149 (17)	0.26792 (17)	0.0655 (9)
C15	0.32556 (18)	0.53634 (16)	0.18843 (16)	0.0550 (8)
C16	0.15632 (19)	0.54289 (18)	0.01765 (16)	0.0592 (8)
C17	0.1480 (2)	0.4246 (2)	−0.01534 (18)	0.0705 (9)
C18	0.0498 (3)	0.3871 (2)	−0.10086 (19)	0.0834 (10)
C19	−0.0397 (2)	0.4662 (3)	−0.15407 (19)	0.0842 (11)
C20	−0.0322 (2)	0.5845 (2)	−0.12320 (19)	0.0760 (10)
C21	0.0649 (2)	0.62309 (19)	−0.03823 (17)	0.0633 (9)
C22	−0.0100 (3)	0.8233 (3)	−0.0472 (2)	0.1089 (13)
H2	0.43954	0.10860	0.08075	0.0752*
H3	0.29570	0.16458	0.23890	0.0791*
H3A	0.36609	0.19688	0.15370	0.0775*
H6	0.22645	−0.14566	0.23738	0.0949*
H7	0.14864	−0.21451	0.31319	0.1261*
H8	0.11179	−0.07923	0.39190	0.1288*
H9	0.14920	0.12855	0.39529	0.1058*
H11A	0.26440	0.30060	0.43607	0.1408*
H11B	0.14394	0.32969	0.34210	0.1408*
H11C	0.25074	0.40345	0.36695	0.1408*
H6A	0.26458	0.66753	0.10045	0.0866*
H13	0.52290	0.60433	0.40746	0.0747*
H14	0.39682	0.69672	0.26167	0.0786*
H17	0.20860	0.37019	0.02014	0.0846*
H18	0.04463	0.30724	−0.12243	0.1002*
H19	−0.10576	0.43986	−0.21125	0.1013*
H20	−0.09290	0.63851	−0.15978	0.0912*
H22A	−0.07363	0.78708	−0.05266	0.1638*
H22B	−0.03118	0.84205	−0.10951	0.1638*
H22C	0.01230	0.89754	−0.01038	0.1638*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1073 (5)	0.0477 (3)	0.0915 (4)	0.0106 (3)	0.0727 (4)	0.0023 (3)
O1	0.1095 (13)	0.0681 (10)	0.0948 (12)	0.0036 (9)	0.0771 (11)	−0.0063 (9)
N1	0.0869 (13)	0.0357 (8)	0.0751 (12)	−0.0041 (8)	0.0547 (11)	−0.0027 (8)
N2	0.0787 (13)	0.0389 (8)	0.0778 (13)	−0.0060 (8)	0.0537 (11)	−0.0029 (8)
N3	0.0868 (14)	0.0455 (9)	0.0894 (14)	0.0022 (9)	0.0654 (12)	0.0000 (9)
C1	0.0654 (13)	0.0360 (9)	0.0545 (13)	0.0019 (9)	0.0350 (11)	0.0012 (9)
C2	0.0921 (17)	0.0368 (9)	0.0779 (16)	−0.0039 (10)	0.0608 (14)	0.0000 (10)
C3	0.0981 (18)	0.0305 (9)	0.0837 (16)	−0.0042 (10)	0.0642 (15)	−0.0031 (10)
C4	0.0581 (13)	0.0406 (10)	0.0582 (13)	0.0001 (9)	0.0338 (11)	0.0015 (9)
C5	0.0549 (13)	0.0675 (13)	0.0651 (14)	−0.0018 (10)	0.0361 (12)	0.0015 (11)
C6	0.0869 (18)	0.0732 (15)	0.099 (2)	−0.0176 (13)	0.0670 (17)	−0.0098 (14)
C7	0.120 (3)	0.100 (2)	0.129 (3)	−0.0425 (18)	0.092 (2)	−0.0195 (19)
C8	0.121 (2)	0.129 (3)	0.112 (2)	−0.048 (2)	0.091 (2)	−0.026 (2)
C9	0.0869 (19)	0.113 (2)	0.0851 (19)	−0.0225 (16)	0.0623 (17)	−0.0181 (16)
C10	0.0607 (15)	0.0811 (16)	0.0631 (15)	−0.0031 (12)	0.0384 (13)	−0.0040 (12)
C11	0.122 (2)	0.0861 (18)	0.097 (2)	0.0192 (16)	0.0780 (19)	−0.0074 (15)
Cl2	0.1150 (5)	0.0491 (3)	0.0793 (4)	0.0085 (3)	0.0634 (4)	0.0085 (3)
O2	0.0938 (13)	0.0507 (9)	0.0976 (12)	0.0108 (8)	0.0489 (11)	0.0039 (8)
N4	0.0806 (13)	0.0349 (8)	0.0777 (13)	0.0005 (8)	0.0572 (11)	−0.0002 (9)
N5	0.0726 (12)	0.0352 (8)	0.0763 (12)	−0.0019 (8)	0.0505 (11)	−0.0007 (8)
N6	0.0799 (14)	0.0406 (9)	0.0811 (14)	−0.0046 (9)	0.0397 (12)	0.0088 (9)
C12	0.0736 (14)	0.0378 (9)	0.0731 (14)	0.0029 (9)	0.0564 (13)	0.0027 (10)
C13	0.0846 (16)	0.0377 (10)	0.0767 (16)	−0.0088 (10)	0.0546 (14)	−0.0064 (10)
C14	0.0877 (17)	0.0320 (9)	0.0839 (17)	−0.0032 (10)	0.0549 (15)	0.0024 (10)
C15	0.0677 (14)	0.0369 (10)	0.0758 (15)	−0.0039 (9)	0.0510 (13)	0.0006 (10)
C16	0.0677 (15)	0.0510 (11)	0.0696 (15)	−0.0030 (11)	0.0466 (13)	0.0021 (11)
C17	0.0809 (17)	0.0608 (13)	0.0805 (17)	0.0063 (12)	0.0537 (15)	−0.0031 (12)
C18	0.106 (2)	0.0732 (15)	0.0828 (19)	−0.0028 (15)	0.0625 (19)	−0.0188 (14)
C19	0.0857 (19)	0.093 (2)	0.0746 (18)	−0.0053 (16)	0.0480 (16)	−0.0130 (15)
C20	0.0761 (18)	0.0790 (16)	0.0781 (18)	0.0104 (13)	0.0487 (16)	0.0077 (14)
C21	0.0755 (16)	0.0548 (12)	0.0738 (16)	0.0020 (11)	0.0521 (15)	0.0042 (11)
C22	0.116 (2)	0.0680 (16)	0.137 (3)	0.0319 (16)	0.072 (2)	0.0163 (17)

Geometric parameters (Å, º) top

Cl1—C1	1.731 (3)	C2—H2	0.9300
Cl2—C12	1.737 (2)	C3—H3A	0.9300
O1—C10	1.374 (3)	C6—H6	0.9300
O1—C11	1.431 (4)	C7—H7	0.9300
O2—C21	1.366 (3)	C8—H8	0.9300
O2—C22	1.422 (4)	C9—H9	0.9300
N1—N2	1.363 (3)	C11—H11B	0.9600
N1—C1	1.296 (3)	C11—H11C	0.9600
N2—C4	1.332 (2)	C11—H11A	0.9600
N3—C5	1.399 (4)	C12—C13	1.395 (3)
N3—C4	1.365 (3)	C13—C14	1.342 (3)
N3—H3	0.8600	C14—C15	1.405 (3)
N4—N5	1.358 (3)	C16—C21	1.395 (4)
N4—C12	1.301 (3)	C16—C17	1.383 (3)
N5—C15	1.337 (2)	C17—C18	1.381 (4)
N6—C15	1.356 (3)	C18—C19	1.366 (5)
N6—C16	1.399 (3)	C19—C20	1.372 (4)
N6—H6A	0.8600	C20—C21	1.374 (4)
C1—C2	1.386 (3)	C13—H13	0.9300
C2—C3	1.343 (4)	C14—H14	0.9300
C3—C4	1.402 (4)	C17—H17	0.9300
C5—C10	1.400 (4)	C18—H18	0.9300
C5—C6	1.388 (3)	C19—H19	0.9300
C6—C7	1.394 (5)	C20—H20	0.9300
C7—C8	1.362 (5)	C22—H22A	0.9600
C8—C9	1.384 (5)	C22—H22B	0.9600
C9—C10	1.371 (4)	C22—H22C	0.9600

C10—O1—C11	118.5 (3)	H11B—C11—H11C	109.00
C21—O2—C22	118.5 (2)	H11A—C11—H11B	110.00
N2—N1—C1	119.43 (16)	O1—C11—H11B	109.00
N1—N2—C4	118.8 (2)	O1—C11—H11C	109.00
C4—N3—C5	131.21 (18)	H11A—C11—H11C	109.00
C5—N3—H3	114.00	O1—C11—H11A	109.00
C4—N3—H3	114.00	N4—C12—C13	124.4 (2)
N5—N4—C12	119.61 (15)	Cl2—C12—N4	116.94 (14)
N4—N5—C15	118.73 (17)	Cl2—C12—C13	118.68 (17)
C15—N6—C16	130.36 (18)	C12—C13—C14	116.5 (2)
C15—N6—H6A	115.00	C13—C14—C15	118.86 (18)
C16—N6—H6A	115.00	N5—C15—C14	121.9 (2)
N1—C1—C2	124.3 (2)	N6—C15—C14	118.47 (17)
Cl1—C1—C2	119.2 (2)	N5—C15—N6	119.65 (19)
Cl1—C1—N1	116.44 (15)	C17—C16—C21	118.5 (2)
C1—C2—C3	116.9 (2)	N6—C16—C17	125.2 (2)
C2—C3—C4	118.53 (18)	N6—C16—C21	116.29 (19)
N2—C4—C3	121.9 (2)	C16—C17—C18	120.1 (3)
N3—C4—C3	118.34 (17)	C17—C18—C19	120.6 (2)
N2—C4—N3	119.8 (2)	C18—C19—C20	120.0 (3)
N3—C5—C10	116.0 (2)	C19—C20—C21	120.0 (3)
N3—C5—C6	125.5 (2)	C16—C21—C20	120.7 (2)
C6—C5—C10	118.5 (3)	O2—C21—C16	114.2 (2)
C5—C6—C7	119.9 (3)	O2—C21—C20	125.1 (2)
C6—C7—C8	120.5 (3)	C12—C13—H13	122.00
C7—C8—C9	120.5 (4)	C14—C13—H13	122.00
C8—C9—C10	119.5 (3)	C13—C14—H14	121.00
C5—C10—C9	121.1 (2)	C15—C14—H14	121.00
O1—C10—C9	124.6 (3)	C16—C17—H17	120.00
O1—C10—C5	114.3 (2)	C18—C17—H17	120.00
C1—C2—H2	122.00	C17—C18—H18	120.00
C3—C2—H2	122.00	C19—C18—H18	120.00
C4—C3—H3A	121.00	C18—C19—H19	120.00
C2—C3—H3A	121.00	C20—C19—H19	120.00
C7—C6—H6	120.00	C19—C20—H20	120.00
C5—C6—H6	120.00	C21—C20—H20	120.00
C6—C7—H7	120.00	O2—C22—H22A	109.00
C8—C7—H7	120.00	O2—C22—H22B	109.00
C7—C8—H8	120.00	O2—C22—H22C	109.00
C9—C8—H8	120.00	H22A—C22—H22B	109.00
C8—C9—H9	120.00	H22A—C22—H22C	110.00
C10—C9—H9	120.00	H22B—C22—H22C	110.00

C11—O1—C10—C5	−177.8 (2)	N3—C5—C6—C7	179.2 (3)
C11—O1—C10—C9	1.7 (4)	C10—C5—C6—C7	−1.7 (4)
C22—O2—C21—C16	−172.8 (3)	N3—C5—C10—O1	−0.4 (3)
C22—O2—C21—C20	8.1 (5)	C6—C5—C10—C9	1.0 (4)
N2—N1—C1—C2	−3.0 (3)	N3—C5—C10—C9	−179.8 (2)
C1—N1—N2—C4	0.0 (3)	C6—C5—C10—O1	−179.6 (2)
N2—N1—C1—Cl1	177.09 (16)	C5—C6—C7—C8	1.0 (5)
N1—N2—C4—C3	2.9 (3)	C6—C7—C8—C9	0.6 (5)
N1—N2—C4—N3	−176.4 (2)	C7—C8—C9—C10	−1.3 (5)
C5—N3—C4—C3	177.8 (2)	C8—C9—C10—O1	−178.9 (3)
C5—N3—C4—N2	−2.9 (4)	C8—C9—C10—C5	0.5 (4)
C4—N3—C5—C6	−3.1 (4)	Cl2—C12—C13—C14	−179.7 (3)
C4—N3—C5—C10	177.8 (2)	N4—C12—C13—C14	0.8 (5)
C12—N4—N5—C15	−1.0 (4)	C12—C13—C14—C15	0.0 (5)
N5—N4—C12—Cl2	−179.8 (2)	C13—C14—C15—N5	−1.3 (5)
N5—N4—C12—C13	−0.3 (5)	C13—C14—C15—N6	179.8 (3)
N4—N5—C15—C14	1.8 (4)	N6—C16—C17—C18	−179.9 (3)
N4—N5—C15—N6	−179.4 (3)	C21—C16—C17—C18	−1.4 (5)
C15—N6—C16—C17	−35.8 (5)	N6—C16—C21—O2	0.8 (4)
C16—N6—C15—N5	14.6 (5)	N6—C16—C21—C20	180.0 (3)
C16—N6—C15—C14	−166.5 (3)	C17—C16—C21—O2	−177.8 (3)
C15—N6—C16—C21	145.7 (3)	C17—C16—C21—C20	1.4 (5)
Cl1—C1—C2—C3	−177.19 (19)	C16—C17—C18—C19	0.5 (6)
N1—C1—C2—C3	2.9 (4)	C17—C18—C19—C20	0.6 (6)
C1—C2—C3—C4	0.1 (4)	C18—C19—C20—C21	−0.7 (5)
C2—C3—C4—N3	176.3 (2)	C19—C20—C21—O2	178.8 (3)
C2—C3—C4—N2	−3.0 (4)	C19—C20—C21—C16	−0.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.86	2.14	2.579 (3)	111
N3—H3···N4	0.86	2.48	3.278 (2)	155
N6—H6A···N1ⁱ	0.86	2.44	3.270 (3)	161
C2—H2···Cl2ⁱⁱ	0.93	2.79	3.526 (2)	137
C3—H3A···N5	0.93	2.61	3.503 (3)	161
C6—H6···N2	0.93	2.31	2.913 (4)	122
C17—H17···N5	0.93	2.50	2.992 (3)	113

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀ClN₃O
M_r	235.67
Crystal system, space group	Monoclinic, P2/c
Temperature (K)	295
a, b, c (Å)	14.6018 (5), 10.8574 (3), 17.4630 (6)
β (°)	126.438 (2)
V (Å³)	2227.29 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.32 × 0.16 × 0.14

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.938, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	17904, 4387, 2815
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.110, 1.03
No. of reflections	4387
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (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—H3···O1	0.86	2.14	2.579 (3)	111
N3—H3···N4	0.86	2.48	3.278 (2)	155
N6—H6A···N1ⁱ	0.86	2.44	3.270 (3)	161
C2—H2···Cl2ⁱⁱ	0.93	2.79	3.526 (2)	137
C3—H3A···N5	0.93	2.61	3.503 (3)	161
C6—H6···N2	0.93	2.31	2.913 (4)	122
C17—H17···N5	0.93	2.50	2.992 (3)	113

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

Acknowledgements

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

References

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