(E)-1-(4-Chloro­benzyl­idene)-2-phenyl­hydrazine

Tahir, M.N.; Tariq, M.I.; Tariq, R.H.; Sarfraz, M.

doi:10.1107/S1600536811032958

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2377

doi:10.1107/S1600536811032958

Open

access

(E)-1-(4-Chlorobenzylidene)-2-phenylhydrazine

M. Nawaz Tahir,^a ^* Muhammad Ilyas Tariq,^b Riaz H. Tariq ^c and Muhammad Sarfraz ^b

^aDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^bDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, and ^cInstitute of Chemical and Pharmaceutical Sciences, The University of Faisalabad, Faisalabad, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 13 August 2011; accepted 14 August 2011; online 27 August 2011)

The asymmetric unit of the title compound, C₁₃H₁₁ClN₂, contains two geometrically distinct molecules; one molecule is close to planar [dihedral angle between the aromatic rings = 2.44 (18)°] and the other is twisted about the linking hydrazide group [dihedral angle = 14.08 (19)°]. In the crystal, the N—H groups do not form hydrogen bonds and the molecules are linked by weak C—H⋯π interactions.

Related literature

For related structures, see: Mufakkar et al. (2010 ); Shad et al. (2010 ); Yin et al. (2007 ).

Experimental

Crystal data

C₁₃H₁₁ClN₂
M_r = 230.69
Orthorhombic, P c a 2₁
a = 18.6896 (9) Å
b = 15.0250 (7) Å
c = 8.4679 (4) Å
V = 2377.9 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 296 K
0.30 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.972, T_max = 0.983
10661 measured reflections
4631 independent reflections
2234 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.107
S = 0.96
4631 reflections
295 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.12 e Å⁻³
Absolute structure: Flack (1983 ), 2120 Friedel pairs
Flack parameter: 0.08 (8)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C14–C19 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cg1ⁱ	0.93	2.91	3.668 (4)	139
C20—H20⋯Cg2ⁱⁱ	0.93	2.73	3.660 (4)	174
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-1, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+1, z]$ .

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/S1600536811032958/hb6364sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032958/hb6364Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032958/hb6364Isup3.cml

checkCIF report

Comment top

We have reported crystal structures of Schiff bases containing phenylhydrazine (E)-1-(2-nitrobenzylidene)-2-phenylhydrazine (Shad et al., 2010) and (E)-1-(4-methoxybenzylidene)-2-phenylhydrazine 2-nitrobenzaldehyde (Mufakkar et al., 2010). The crystal structure of (E)-N- (2,4-dichlorobenzylidene)-N^'-phenylhydrazine (Yin, et al., 2007) has been published which is related to the title compound (I), (Fig. 1).

The title compound consists of two molecules in the crystallographic asymmetric unit which differ from each other geometrically. In one molecule, the benzene ring A (C1—C6) of phenylhydrazine and group B (C8—C13/CL1) of 4-chlorobenzaldehyde are planar with r.m.s. deviation of 0.006 and 0.018 Å, respectively. The Schiff base group C (C7/N1/N2) is of course planar. The dihedral angle between A/B, A/C and B/C is 14.62 (16)°, 8.18 (51)° and 9.86 (48)°, respectively. In second molecule, the benzene ring D (C14—C19) and group E (C21—C26) of 4-chlorobenzaldehyde are also almost planar with r.m.s. deviations of 0.004 and 0.016 Å, respectively. The dihedral angle between D/E is 2.84 (15)°. The central group F (C20/N3/N4) of this molecule makes dihedral angle of 3.10 (41)° with group D, whereas it is oriented at 0.99 (43)° with group E. This molecule is therefore, essentially planar with r.m.s. deviation of 0.026 Å. The molecules are consolidated due to van Der Wal and C—H···π interactions (Table 1).

Related literature top

For related structures, see: Mufakkar et al. (2010); Shad et al. (2010); Yin et al. (2007).

Experimental top

Equimolar quantities of phenylhydrazine and 4-chlorobenzaldehyde were refluxed in methanol for 30 min resulting in light yellow solution. The solution was kept at room temperature which affoarded yellow prisms after 72 h.

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 displacement ellipsoids drawn at the 50% probability level.

(E)-1-(4-Chlorobenzylidene)-2-phenylhydrazine top

Crystal data top

C₁₃H₁₁ClN₂	F(000) = 960
M_r = 230.69	D_x = 1.289 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2234 reflections
a = 18.6896 (9) Å	θ = 2.6–26.0°
b = 15.0250 (7) Å	µ = 0.29 mm⁻¹
c = 8.4679 (4) Å	T = 296 K
V = 2377.9 (2) Å³	Prism, yellow
Z = 8	0.30 × 0.22 × 0.18 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4631 independent reflections
Radiation source: fine-focus sealed tube	2234 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 7.80 pixels mm^-1	θ_max = 26.0°, θ_min = 2.6°
ω scans	h = −23→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −18→8
T_min = 0.972, T_max = 0.983	l = −10→10
10661 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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.034P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max < 0.001
4631 reflections	Δρ_max = 0.15 e Å⁻³
295 parameters	Δρ_min = −0.12 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2120 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (8)

Crystal data top

C₁₃H₁₁ClN₂	V = 2377.9 (2) Å³
M_r = 230.69	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 18.6896 (9) Å	µ = 0.29 mm⁻¹
b = 15.0250 (7) Å	T = 296 K
c = 8.4679 (4) Å	0.30 × 0.22 × 0.18 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4631 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2234 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.983	R_int = 0.047
10661 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	Δρ_max = 0.15 e Å⁻³
S = 0.96	Δρ_min = −0.12 e Å⁻³
4631 reflections	Absolute structure: Flack (1983), 2120 Friedel pairs
295 parameters	Absolute structure parameter: 0.08 (8)
1 restraint

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.65074 (8)	−0.28852 (7)	0.04443 (17)	0.1121 (6)
N1	0.7409 (2)	0.2275 (3)	0.1957 (4)	0.0747 (16)
N2	0.71259 (15)	0.1473 (2)	0.1565 (3)	0.0620 (12)
C1	0.7116 (2)	0.3043 (3)	0.1339 (4)	0.0570 (17)
C2	0.6470 (2)	0.3045 (2)	0.0531 (5)	0.0600 (16)
C3	0.6199 (2)	0.3839 (3)	−0.0015 (4)	0.0680 (16)
C4	0.6544 (2)	0.4633 (3)	0.0205 (5)	0.0700 (17)
C5	0.7189 (2)	0.4618 (3)	0.0988 (4)	0.0733 (17)
C6	0.7466 (2)	0.3843 (3)	0.1566 (5)	0.0667 (16)
C7	0.7460 (2)	0.0782 (3)	0.2017 (4)	0.0660 (17)
C8	0.7209 (2)	−0.0111 (3)	0.1679 (5)	0.0610 (16)
C9	0.6539 (2)	−0.0276 (3)	0.1025 (4)	0.0690 (17)
C10	0.6317 (2)	−0.1110 (3)	0.0677 (4)	0.0733 (17)
C11	0.6769 (3)	−0.1823 (3)	0.0953 (5)	0.0763 (19)
C12	0.7428 (3)	−0.1686 (3)	0.1634 (6)	0.0880 (19)
C13	0.7642 (2)	−0.0834 (3)	0.1987 (5)	0.0830 (17)
Cl2	0.05113 (6)	0.19759 (6)	0.67491 (15)	0.0891 (5)
N3	0.09142 (18)	0.7174 (2)	0.4688 (4)	0.0713 (14)
N4	0.07889 (14)	0.6368 (2)	0.5353 (3)	0.0569 (11)
C14	0.07671 (18)	0.7951 (2)	0.5497 (4)	0.0550 (14)
C15	0.0503 (2)	0.7956 (3)	0.7018 (4)	0.0627 (17)
C16	0.0368 (2)	0.8752 (3)	0.7763 (5)	0.0723 (17)
C17	0.0484 (2)	0.9564 (3)	0.7053 (5)	0.0727 (17)
C18	0.0740 (2)	0.9553 (3)	0.5522 (5)	0.0740 (19)
C19	0.0884 (2)	0.8767 (3)	0.4756 (5)	0.0670 (17)
C20	0.09573 (19)	0.5686 (3)	0.4543 (4)	0.0613 (16)
C21	0.08497 (18)	0.4782 (2)	0.5112 (4)	0.0527 (14)
C22	0.1035 (2)	0.4073 (3)	0.4174 (4)	0.0730 (16)
C23	0.0947 (2)	0.3208 (3)	0.4663 (5)	0.0763 (17)
C24	0.0658 (2)	0.3056 (3)	0.6128 (4)	0.0580 (16)
C25	0.0479 (2)	0.3741 (3)	0.7092 (4)	0.0617 (16)
C26	0.05611 (19)	0.4603 (2)	0.6581 (5)	0.0590 (14)
H1	0.782 (2)	0.228 (2)	0.231 (5)	0.0899*
H2	0.62234	0.25154	0.03615	0.0718*
H3	0.57649	0.38355	−0.05530	0.0817*
H4	0.63493	0.51639	−0.01617	0.0842*
H5	0.74414	0.51457	0.11255	0.0878*
H6	0.78957	0.38538	0.21195	0.0798*
H7	0.78820	0.08512	0.25863	0.0790*
H9	0.62358	0.02012	0.08204	0.0825*
H10	0.58637	−0.12036	0.02547	0.0879*
H12	0.77257	−0.21656	0.18531	0.1056*
H13	0.80890	−0.07435	0.24434	0.0998*
H3A	0.113 (2)	0.720 (2)	0.369 (4)	0.0858*
H15	0.04156	0.74218	0.75390	0.0750*
H16	0.01907	0.87411	0.87893	0.0867*
H17	0.03937	1.00953	0.75794	0.0874*
H18	0.08167	1.00894	0.49998	0.0888*
H19	0.10607	0.87791	0.37294	0.0803*
H20	0.11570	0.57692	0.35474	0.0736*
H22	0.12260	0.41816	0.31781	0.0874*
H23	0.10806	0.27364	0.40153	0.0915*
H25	0.03018	0.36272	0.80979	0.0739*
H26	0.04206	0.50705	0.72297	0.0710*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1692 (12)	0.0627 (8)	0.1044 (9)	−0.0202 (8)	−0.0151 (10)	0.0053 (7)
N1	0.067 (3)	0.063 (2)	0.094 (3)	−0.002 (2)	−0.019 (2)	−0.004 (2)
N2	0.063 (2)	0.056 (2)	0.067 (2)	0.0003 (18)	−0.0010 (19)	−0.003 (2)
C1	0.055 (3)	0.060 (3)	0.056 (3)	−0.003 (2)	0.006 (2)	−0.013 (2)
C2	0.062 (3)	0.056 (3)	0.062 (2)	−0.009 (2)	−0.005 (2)	−0.010 (2)
C3	0.070 (3)	0.072 (3)	0.062 (2)	0.004 (2)	−0.012 (2)	−0.003 (2)
C4	0.087 (3)	0.056 (3)	0.067 (3)	−0.001 (2)	0.002 (2)	−0.010 (2)
C5	0.079 (3)	0.064 (3)	0.077 (3)	−0.017 (2)	0.011 (2)	−0.016 (2)
C6	0.057 (2)	0.064 (3)	0.079 (3)	−0.005 (2)	−0.001 (2)	−0.012 (3)
C7	0.060 (3)	0.068 (3)	0.070 (3)	0.004 (3)	−0.008 (2)	−0.004 (2)
C8	0.056 (3)	0.065 (3)	0.062 (2)	0.004 (2)	−0.006 (2)	−0.002 (2)
C9	0.069 (3)	0.061 (3)	0.077 (3)	0.007 (2)	−0.006 (2)	0.000 (2)
C10	0.077 (3)	0.074 (3)	0.069 (3)	−0.001 (3)	−0.007 (2)	0.002 (3)
C11	0.101 (4)	0.062 (3)	0.066 (3)	−0.015 (3)	0.000 (3)	0.009 (2)
C12	0.100 (4)	0.058 (3)	0.106 (3)	0.011 (3)	−0.009 (3)	0.011 (3)
C13	0.070 (3)	0.072 (3)	0.107 (3)	0.008 (3)	−0.023 (3)	0.013 (3)
Cl2	0.1246 (9)	0.0516 (7)	0.0911 (8)	−0.0030 (6)	−0.0040 (8)	0.0068 (7)
N3	0.104 (3)	0.049 (2)	0.061 (2)	0.0020 (19)	0.0193 (19)	0.0028 (18)
N4	0.068 (2)	0.044 (2)	0.0586 (19)	0.0062 (16)	−0.0039 (17)	0.0035 (17)
C14	0.060 (2)	0.049 (3)	0.056 (2)	0.0028 (19)	0.001 (2)	0.000 (2)
C15	0.077 (3)	0.051 (3)	0.060 (3)	0.007 (2)	0.004 (2)	0.013 (2)
C16	0.084 (3)	0.063 (3)	0.070 (3)	0.009 (2)	0.012 (2)	−0.003 (2)
C17	0.088 (3)	0.060 (3)	0.070 (3)	−0.004 (2)	−0.001 (2)	0.007 (2)
C18	0.088 (3)	0.041 (3)	0.093 (4)	−0.004 (2)	−0.003 (3)	0.014 (2)
C19	0.076 (3)	0.057 (3)	0.068 (3)	−0.002 (2)	0.011 (2)	0.014 (2)
C20	0.074 (3)	0.057 (3)	0.053 (2)	0.004 (2)	0.004 (2)	0.000 (2)
C21	0.062 (3)	0.043 (2)	0.053 (2)	0.0034 (18)	0.0001 (19)	−0.0053 (19)
C22	0.099 (3)	0.060 (3)	0.060 (2)	0.006 (2)	0.018 (2)	−0.001 (2)
C23	0.102 (3)	0.059 (3)	0.068 (3)	0.014 (2)	0.010 (2)	−0.012 (2)
C24	0.069 (3)	0.042 (2)	0.063 (3)	−0.002 (2)	−0.010 (2)	0.0058 (19)
C25	0.081 (3)	0.053 (3)	0.051 (2)	0.001 (2)	0.003 (2)	0.003 (2)
C26	0.069 (2)	0.056 (3)	0.052 (2)	0.012 (2)	0.003 (2)	−0.011 (2)

Geometric parameters (Å, º) top

Cl1—C11	1.724 (5)	C7—H7	0.9300
Cl2—C24	1.728 (4)	C9—H9	0.9300
N1—N2	1.357 (5)	C10—H10	0.9300
N1—C1	1.380 (6)	C12—H12	0.9300
N2—C7	1.271 (5)	C13—H13	0.9300
N1—H1	0.82 (4)	C14—C19	1.395 (5)
N3—C14	1.381 (4)	C14—C15	1.379 (5)
N3—N4	1.356 (4)	C15—C16	1.376 (6)
N4—C20	1.273 (5)	C16—C17	1.377 (6)
N3—H3A	0.94 (3)	C17—C18	1.382 (6)
C1—C6	1.382 (6)	C18—C19	1.374 (6)
C1—C2	1.388 (5)	C20—C21	1.455 (5)
C2—C3	1.376 (5)	C21—C26	1.382 (5)
C3—C4	1.369 (6)	C21—C22	1.373 (5)
C4—C5	1.376 (5)	C22—C23	1.374 (6)
C5—C6	1.365 (6)	C23—C24	1.372 (5)
C7—C8	1.450 (6)	C24—C25	1.356 (6)
C8—C13	1.380 (6)	C25—C26	1.374 (5)
C8—C9	1.392 (5)	C15—H15	0.9300
C9—C10	1.353 (6)	C16—H16	0.9300
C10—C11	1.384 (6)	C17—H17	0.9300
C11—C12	1.376 (8)	C18—H18	0.9300
C12—C13	1.374 (6)	C19—H19	0.9300
C2—H2	0.9300	C20—H20	0.9300
C3—H3	0.9300	C22—H22	0.9300
C4—H4	0.9300	C23—H23	0.9300
C5—H5	0.9300	C25—H25	0.9300
C6—H6	0.9300	C26—H26	0.9300

N2—N1—C1	119.7 (3)	C11—C12—H12	120.00
N1—N2—C7	117.4 (3)	C13—C12—H12	120.00
N2—N1—H1	117 (2)	C12—C13—H13	119.00
C1—N1—H1	120 (2)	C8—C13—H13	119.00
N4—N3—C14	121.0 (3)	N3—C14—C15	122.6 (3)
N3—N4—C20	116.9 (3)	N3—C14—C19	119.3 (3)
C14—N3—H3A	119.8 (19)	C15—C14—C19	118.1 (3)
N4—N3—H3A	119.1 (19)	C14—C15—C16	119.9 (4)
N1—C1—C6	119.1 (4)	C15—C16—C17	122.8 (4)
N1—C1—C2	122.3 (4)	C16—C17—C18	117.0 (4)
C2—C1—C6	118.6 (4)	C17—C18—C19	121.4 (4)
C1—C2—C3	119.2 (3)	C14—C19—C18	120.8 (4)
C2—C3—C4	122.4 (4)	N4—C20—C21	122.6 (3)
C3—C4—C5	117.7 (4)	C22—C21—C26	117.9 (3)
C4—C5—C6	121.3 (4)	C20—C21—C22	119.9 (3)
C1—C6—C5	120.8 (4)	C20—C21—C26	122.2 (3)
N2—C7—C8	122.5 (3)	C21—C22—C23	122.0 (3)
C7—C8—C9	122.3 (4)	C22—C23—C24	118.5 (4)
C7—C8—C13	120.1 (4)	Cl2—C24—C25	119.4 (3)
C9—C8—C13	117.6 (4)	Cl2—C24—C23	119.6 (3)
C8—C9—C10	121.9 (4)	C23—C24—C25	121.0 (4)
C9—C10—C11	119.5 (4)	C24—C25—C26	119.9 (3)
Cl1—C11—C12	119.8 (4)	C21—C26—C25	120.7 (3)
C10—C11—C12	120.1 (4)	C14—C15—H15	120.00
Cl1—C11—C10	120.1 (4)	C16—C15—H15	120.00
C11—C12—C13	119.4 (4)	C15—C16—H16	119.00
C8—C13—C12	121.5 (4)	C17—C16—H16	119.00
C3—C2—H2	120.00	C16—C17—H17	122.00
C1—C2—H2	120.00	C18—C17—H17	122.00
C2—C3—H3	119.00	C17—C18—H18	119.00
C4—C3—H3	119.00	C19—C18—H18	119.00
C3—C4—H4	121.00	C14—C19—H19	120.00
C5—C4—H4	121.00	C18—C19—H19	120.00
C4—C5—H5	119.00	N4—C20—H20	119.00
C6—C5—H5	119.00	C21—C20—H20	119.00
C5—C6—H6	120.00	C21—C22—H22	119.00
C1—C6—H6	120.00	C23—C22—H22	119.00
C8—C7—H7	119.00	C22—C23—H23	121.00
N2—C7—H7	119.00	C24—C23—H23	121.00
C8—C9—H9	119.00	C24—C25—H25	120.00
C10—C9—H9	119.00	C26—C25—H25	120.00
C11—C10—H10	120.00	C21—C26—H26	120.00
C9—C10—H10	120.00	C25—C26—H26	120.00

C1—N1—N2—C7	172.3 (3)	C9—C10—C11—C12	2.5 (6)
N2—N1—C1—C2	10.7 (5)	C10—C11—C12—C13	−2.2 (7)
N2—N1—C1—C6	−171.1 (3)	Cl1—C11—C12—C13	177.8 (4)
N1—N2—C7—C8	179.6 (3)	C11—C12—C13—C8	0.3 (7)
N4—N3—C14—C19	−178.2 (3)	N3—C14—C15—C16	179.9 (3)
C14—N3—N4—C20	−178.2 (3)	C19—C14—C15—C16	−0.5 (5)
N4—N3—C14—C15	1.4 (5)	N3—C14—C19—C18	179.7 (3)
N3—N4—C20—C21	−179.8 (3)	C15—C14—C19—C18	0.0 (5)
N1—C1—C2—C3	178.2 (4)	C14—C15—C16—C17	0.1 (6)
N1—C1—C6—C5	−179.3 (4)	C15—C16—C17—C18	0.7 (6)
C2—C1—C6—C5	−1.0 (6)	C16—C17—C18—C19	−1.1 (6)
C6—C1—C2—C3	−0.1 (6)	C17—C18—C19—C14	0.8 (6)
C1—C2—C3—C4	0.2 (6)	N4—C20—C21—C22	179.3 (3)
C2—C3—C4—C5	0.8 (6)	N4—C20—C21—C26	−0.5 (5)
C3—C4—C5—C6	−1.9 (6)	C20—C21—C22—C23	179.7 (3)
C4—C5—C6—C1	2.0 (6)	C26—C21—C22—C23	−0.6 (5)
N2—C7—C8—C13	170.3 (4)	C20—C21—C26—C25	−178.8 (3)
N2—C7—C8—C9	−8.9 (6)	C22—C21—C26—C25	1.4 (5)
C13—C8—C9—C10	−0.9 (6)	C21—C22—C23—C24	0.7 (6)
C7—C8—C13—C12	−178.0 (4)	C22—C23—C24—Cl2	177.7 (3)
C7—C8—C9—C10	178.3 (4)	C22—C23—C24—C25	−1.6 (6)
C9—C8—C13—C12	1.3 (6)	Cl2—C24—C25—C26	−176.9 (3)
C8—C9—C10—C11	−1.0 (6)	C23—C24—C25—C26	2.5 (6)
C9—C10—C11—Cl1	−177.5 (3)	C24—C25—C26—C21	−2.4 (6)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C14–C19 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg1ⁱ	0.93	2.91	3.668 (4)	139
C20—H20···Cg2ⁱⁱ	0.93	2.73	3.660 (4)	174

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁ClN₂
M_r	230.69
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	296
a, b, c (Å)	18.6896 (9), 15.0250 (7), 8.4679 (4)
V (Å³)	2377.9 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.30 × 0.22 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.972, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	10661, 4631, 2234
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.107, 0.96
No. of reflections	4631
No. of parameters	295
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.12
Absolute structure	Flack (1983), 2120 Friedel pairs
Absolute structure parameter	0.08 (8)

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

Cg1 and Cg2 are the centroids of the C14–C19 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg1ⁱ	0.93	2.91	3.668 (4)	139
C20—H20···Cg2ⁱⁱ	0.93	2.73	3.660 (4)	174

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, former Vice Chancellor, University of Sargodha. Pakistan.

References

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
Mufakkar, M., Tahir, M. N., Tariq, M. I., Ahmad, S. & Sarfraz, M. (2010). Acta Cryst. E66, o1887. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shad, H. A., Tahir, M. N., Tariq, M. I., Sarfraz, M. & Ahmad, S. (2010). Acta Cryst. E66, o1955. CrossRef 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
Yin, Z.-G., Qian, H.-Y., Chen, Y.-Z. & Feng, Y.-L. (2007). Acta Cryst. E63, o4119. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2377

doi:10.1107/S1600536811032958

Open

access