{5-Chloro-2-[(2-hy­droxy­benzyl­idene)amino]­phen­yl}(phen­yl)methanone

Aslam, M.; Anis, I.; Afza, N.; Nelofar, A.; Yousuf, S.

doi:10.1107/S1600536811048690

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages o3442-o3443

https://doi.org/10.1107/S1600536811048690

Open

access

{5-Chloro-2-[(2-hydroxybenzylidene)amino]phenyl}(phenyl)methanone

M. Aslam,^a,^b ^* I. Anis,^b N. Afza,^a A. Nelofar ^a and S. Yousuf ^c ^*

^aPharmaceutical Research Centre, PCSIR Laboratories Complex, Karachi, Pakistan, ^bDepartment of Chemistry, University of Karachi, Karachi, Pakistan, and ^cH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
^*Correspondence e-mail: maslamchemist@hotmail.com, dr.sammer.yousuf@gmail.com

(Received 5 November 2011; accepted 16 November 2011; online 25 November 2011)

The title Schiff base compound, C₂₀H₁₄ClNO₂, adopts an E configuration about the azomethine bond. The phenol and chlorobenzene rings form dihedral angles of 84.71 (9) and 80.70 (8)°, respectively, with the phenyl ring and are twisted by 15.32 (8)° with respect to one another. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond, which forms an S(6) ring motif. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming columns parallel to the a axis.

Related literature

For the biological activity of Schiff bases, see: Khan et al. (2009 ); Gerdemann et al. (2002 ); Samadhiya & Halve (2001 ); Mallikarjun & Sangamesh (1997 ); Fioravanti et al. (1995 ); Solomon & Lowery (1993 ). For related structures, see: Aslam et al. (2011 ); Zeb & Yousuf (2011 ); Cox et al. (2008 ); Vasco-Mendez et al. (1996 ).

Experimental

Crystal data

C₂₀H₁₄ClNO₂
M_r = 335.77
Triclinic, $[P \overline 1]$
a = 7.3904 (9) Å
b = 10.7933 (14) Å
c = 10.8999 (14) Å
α = 73.120 (2)°
β = 87.919 (3)°
γ = 82.953 (3)°
V = 825.71 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 273 K
0.43 × 0.19 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.903, T_max = 0.962
9338 measured reflections
3066 independent reflections
2481 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.109
S = 1.03
3066 reflections
221 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N1	0.89 (2)	1.80 (2)	2.6188 (19)	152 (2)
C7—H7A⋯O1ⁱ	0.93	2.57	3.353 (2)	142
C17—H17A⋯O1ⁱⁱ	0.93	2.48	3.340 (2)	155
Symmetry codes: (i) -x+1, -y, -z+2; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811048690/rz2667sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048690/rz2667Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811048690/rz2667Isup3.cml

checkCIF report

Comment top

Schiff bases are well known ligands in coordination chemistry with a wide range of biological activities (Khan et al., 2009; Gerdemann et al., 2002; Samadhiya & Halve, 2001; Mallikarjun & Sangamesh, 1997; Fioravanti et al., 1995; Solomon & Lowery, 1993). The title compound was prepared as a part of our ongoing research on bioactive compounds.

The structure of title compound (Fig. 1) is similar to that of the recently reported compound {5-chloro-2-[(4-nitrobenzylidene)amino]phenyl}(phenyl)methanone (Aslam et al., 2011) with the difference that the nitrobenzene moiety is replaced by a phenol group. The phenol (C1-C6) and clorobenzene (C8-C13) rings are twisted by 15.32 (8)° and form dihedral angles of 84.71 (9)° and 80.70 (8)°, respectively, with the phenyl ring (C15-C20). The azomethine C═N double bond adopts an E configuration, with the C8/N1/C6-C7 torsion angle of 178.60 (13)°. The molecular conformation is stabilized by an O2—H2A···N1 intramolecular hydrogen bond (Table 1) to form a S6 ring motif (Fig. 1). Bond lengths and angles are similar to those observed in other structurally related compounds (Aslam et al., 2011; Cox et al., 2008; Vasco-Mendez et al., 1996; Zeb & Yousuf, 2011). In the crystal structure, the molecules are linked to form columns parallel to the a axis (Fig. 2) via C7—H7A···O1 and C17—H17A···O1 intermolecular hydrogen bonds (Table 1).

Related literature top

For the biological activity of Schiff bases, see: Khan et al. (2009); Gerdemann et al. (2002); Samadhiya & Halve (2001); Mallikarjun & Sangamesh (1997); Fioravanti et al. (1995); Solomon & Lowery (1993). For related structures, see: Aslam et al. (2011); Zeb & Yousuf (2011); Cox et al. (2008); Vasco-Mendez et al. (1996).

Experimental top

The synthesis of title compound was carried out by refluxing a mixture of salicylaldehyde (1 mol) and 2-amino-5-chlorobenzophenone (1 mol) in ethanol (50 ml) along with 3 drops of conc. H₂SO₄ for 5 h at 343 K. After cooling the mixture was concentrated to one third under reduced pressure followed by addition of ethyl acetate (10 ml) and chloroforom (10 ml). The mixture was kept at room temperature and yellow crystals were obtained after seven days. The crystalline product was collected, washed with methanol and dried to afford the title compound in 85% yield. Slow evaporation of a methanol solution afforded yellow crystals found suitable for single-crystal X-ray diffraction studies. All chemicals were purchased from Sigma-Aldrich.

Structure description top

For the biological activity of Schiff bases, see: Khan et al. (2009); Gerdemann et al. (2002); Samadhiya & Halve (2001); Mallikarjun & Sangamesh (1997); Fioravanti et al. (1995); Solomon & Lowery (1993). For related structures, see: Aslam et al. (2011); Zeb & Yousuf (2011); Cox et al. (2008); Vasco-Mendez et al. (1996).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the b axis. Hydrogen atoms not involved in hydrogen bonding (dashed lines) are omitted.

{5-Chloro-2-[(2-hydroxybenzylidene)amino]phenyl}(phenyl)methanone top

Crystal data top

C₂₀H₁₄ClNO₂	Z = 2
M_r = 335.77	F(000) = 348
Triclinic, P1	D_x = 1.351 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3904 (9) Å	Cell parameters from 3265 reflections
b = 10.7933 (14) Å	θ = 2.0–25.5°
c = 10.8999 (14) Å	µ = 0.24 mm⁻¹
α = 73.120 (2)°	T = 273 K
β = 87.919 (3)°	Block, yellow
γ = 82.953 (3)°	0.43 × 0.19 × 0.16 mm
V = 825.71 (18) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3066 independent reflections
Radiation source: fine-focus sealed tube	2481 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ω scan	θ_max = 25.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
T_min = 0.903, T_max = 0.962	k = −13→13
9338 measured reflections	l = −13→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0541P)² + 0.1538P] where P = (F_o² + 2F_c²)/3
3066 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.17 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₀H₁₄ClNO₂	γ = 82.953 (3)°
M_r = 335.77	V = 825.71 (18) Å³
Triclinic, P1	Z = 2
a = 7.3904 (9) Å	Mo Kα radiation
b = 10.7933 (14) Å	µ = 0.24 mm⁻¹
c = 10.8999 (14) Å	T = 273 K
α = 73.120 (2)°	0.43 × 0.19 × 0.16 mm
β = 87.919 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3066 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2481 reflections with I > 2σ(I)
T_min = 0.903, T_max = 0.962	R_int = 0.016
9338 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.17 e Å⁻³
3066 reflections	Δρ_min = −0.20 e Å⁻³
221 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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	0.31204 (8)	0.24660 (5)	0.46997 (5)	0.0854 (2)
O1	0.59969 (16)	−0.21801 (12)	0.84282 (15)	0.0757 (4)
O2	0.2754 (2)	−0.32066 (12)	1.15776 (14)	0.0788 (4)
H2A	0.279 (3)	−0.254 (2)	1.0879 (11)	0.103 (8)*
N1	0.26996 (17)	−0.08203 (12)	1.00695 (12)	0.0487 (3)
C1	0.2475 (2)	−0.26589 (17)	1.25483 (17)	0.0612 (4)
C2	0.2341 (3)	−0.3472 (2)	1.3787 (2)	0.0828 (6)
H2B	0.2496	−0.4372	1.3938	0.099*
C3	0.1979 (3)	−0.2949 (3)	1.4788 (2)	0.0882 (7)
H3A	0.1878	−0.3502	1.5613	0.106*
C4	0.1761 (3)	−0.1621 (3)	1.45934 (19)	0.0817 (6)
H4A	0.1495	−0.1278	1.5279	0.098*
C5	0.1939 (2)	−0.0807 (2)	1.33794 (17)	0.0657 (5)
H5A	0.1819	0.0089	1.3249	0.079*
C6	0.2299 (2)	−0.13059 (16)	1.23310 (15)	0.0519 (4)
C7	0.2450 (2)	−0.04203 (15)	1.10631 (15)	0.0490 (4)
H7A	0.2363	0.0470	1.0967	0.059*
C8	0.28094 (19)	0.00455 (14)	0.88212 (14)	0.0454 (3)
C9	0.2189 (2)	0.13726 (15)	0.84612 (16)	0.0541 (4)
H9A	0.1692	0.1759	0.9076	0.065*
C10	0.2302 (2)	0.21192 (15)	0.72062 (17)	0.0580 (4)
H10A	0.1894	0.3006	0.6976	0.070*
C11	0.3023 (2)	0.15451 (16)	0.62954 (16)	0.0557 (4)
C12	0.3654 (2)	0.02359 (16)	0.66243 (16)	0.0550 (4)
H12A	0.4144	−0.0142	0.6001	0.066*
C13	0.3554 (2)	−0.05126 (14)	0.78849 (15)	0.0463 (4)
C14	0.4369 (2)	−0.19231 (15)	0.82362 (15)	0.0487 (4)
C15	0.3180 (2)	−0.29461 (14)	0.83004 (14)	0.0449 (3)
C16	0.1298 (2)	−0.26661 (16)	0.81996 (15)	0.0529 (4)
H16A	0.0760	−0.1813	0.8075	0.063*
C17	0.0220 (2)	−0.36421 (18)	0.82830 (17)	0.0626 (5)
H17A	−0.1041	−0.3450	0.8220	0.075*
C18	0.1019 (3)	−0.49073 (17)	0.84612 (18)	0.0657 (5)
H18A	0.0294	−0.5568	0.8520	0.079*
C19	0.2881 (3)	−0.51924 (16)	0.85517 (19)	0.0672 (5)
H19A	0.3412	−0.6045	0.8667	0.081*
C20	0.3961 (2)	−0.42217 (15)	0.84726 (16)	0.0558 (4)
H20A	0.5221	−0.4421	0.8535	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1056 (4)	0.0725 (3)	0.0594 (3)	−0.0004 (3)	0.0066 (3)	0.0054 (2)
O1	0.0506 (7)	0.0541 (7)	0.1234 (12)	0.0019 (5)	−0.0083 (7)	−0.0295 (7)
O2	0.1159 (12)	0.0473 (7)	0.0672 (9)	−0.0021 (7)	0.0064 (8)	−0.0111 (7)
N1	0.0531 (7)	0.0435 (7)	0.0492 (8)	−0.0035 (6)	0.0016 (6)	−0.0137 (6)
C1	0.0636 (11)	0.0598 (10)	0.0556 (10)	−0.0029 (8)	−0.0010 (8)	−0.0113 (8)
C2	0.0990 (16)	0.0672 (12)	0.0684 (13)	−0.0047 (11)	−0.0030 (11)	0.0004 (10)
C3	0.0985 (16)	0.1036 (18)	0.0499 (11)	−0.0121 (13)	−0.0008 (10)	−0.0024 (11)
C4	0.0866 (14)	0.1068 (18)	0.0524 (11)	−0.0116 (12)	0.0000 (10)	−0.0237 (11)
C5	0.0666 (11)	0.0776 (12)	0.0561 (11)	−0.0078 (9)	−0.0022 (8)	−0.0241 (9)
C6	0.0455 (8)	0.0593 (10)	0.0506 (9)	−0.0053 (7)	−0.0025 (7)	−0.0152 (7)
C7	0.0470 (8)	0.0467 (8)	0.0546 (9)	−0.0046 (6)	−0.0012 (7)	−0.0171 (7)
C8	0.0447 (8)	0.0415 (8)	0.0506 (9)	−0.0056 (6)	0.0003 (6)	−0.0139 (7)
C9	0.0634 (10)	0.0412 (8)	0.0596 (10)	−0.0012 (7)	0.0017 (8)	−0.0196 (7)
C10	0.0666 (10)	0.0385 (8)	0.0650 (11)	−0.0022 (7)	−0.0036 (8)	−0.0103 (8)
C11	0.0580 (10)	0.0499 (9)	0.0536 (9)	−0.0073 (7)	0.0001 (7)	−0.0058 (7)
C12	0.0596 (10)	0.0524 (9)	0.0520 (9)	−0.0025 (7)	0.0058 (7)	−0.0160 (7)
C13	0.0451 (8)	0.0407 (8)	0.0533 (9)	−0.0054 (6)	0.0017 (6)	−0.0143 (7)
C14	0.0503 (9)	0.0450 (8)	0.0507 (9)	−0.0005 (7)	0.0033 (7)	−0.0159 (7)
C15	0.0519 (8)	0.0416 (8)	0.0401 (8)	−0.0008 (6)	0.0008 (6)	−0.0122 (6)
C16	0.0542 (9)	0.0477 (9)	0.0551 (9)	0.0013 (7)	0.0013 (7)	−0.0153 (7)
C17	0.0517 (9)	0.0691 (11)	0.0684 (11)	−0.0096 (8)	0.0044 (8)	−0.0217 (9)
C18	0.0742 (12)	0.0551 (10)	0.0701 (12)	−0.0202 (9)	0.0031 (9)	−0.0167 (9)
C19	0.0777 (13)	0.0423 (9)	0.0805 (13)	−0.0027 (8)	−0.0081 (10)	−0.0169 (8)
C20	0.0565 (9)	0.0457 (9)	0.0640 (10)	0.0024 (7)	−0.0046 (8)	−0.0167 (8)

Geometric parameters (Å, º) top

Cl1—C11	1.7386 (17)	C9—C10	1.377 (2)
O1—C14	1.2125 (18)	C9—H9A	0.9300
O2—C1	1.352 (2)	C10—C11	1.375 (2)
O2—H2A	0.882 (19)	C10—H10A	0.9300
N1—C7	1.277 (2)	C11—C12	1.378 (2)
N1—C8	1.4154 (19)	C12—C13	1.382 (2)
C1—C2	1.388 (3)	C12—H12A	0.9300
C1—C6	1.400 (2)	C13—C14	1.510 (2)
C2—C3	1.371 (3)	C14—C15	1.479 (2)
C2—H2B	0.9300	C15—C16	1.388 (2)
C3—C4	1.377 (3)	C15—C20	1.388 (2)
C3—H3A	0.9300	C16—C17	1.377 (2)
C4—C5	1.371 (3)	C16—H16A	0.9300
C4—H4A	0.9300	C17—C18	1.381 (3)
C5—C6	1.402 (2)	C17—H17A	0.9300
C5—H5A	0.9300	C18—C19	1.373 (3)
C6—C7	1.444 (2)	C18—H18A	0.9300
C7—H7A	0.9300	C19—C20	1.375 (2)
C8—C9	1.393 (2)	C19—H19A	0.9300
C8—C13	1.393 (2)	C20—H20A	0.9300

C1—O2—H2A	105.0 (12)	C9—C10—H10A	120.2
C7—N1—C8	122.32 (13)	C10—C11—C12	120.90 (15)
O2—C1—C2	118.41 (17)	C10—C11—Cl1	120.10 (13)
O2—C1—C6	121.81 (15)	C12—C11—Cl1	119.00 (14)
C2—C1—C6	119.78 (18)	C11—C12—C13	119.61 (15)
C3—C2—C1	120.0 (2)	C11—C12—H12A	120.2
C3—C2—H2B	120.0	C13—C12—H12A	120.2
C1—C2—H2B	120.0	C12—C13—C8	120.47 (14)
C2—C3—C4	121.19 (19)	C12—C13—C14	118.56 (14)
C2—C3—H3A	119.4	C8—C13—C14	120.87 (13)
C4—C3—H3A	119.4	O1—C14—C15	121.85 (14)
C5—C4—C3	119.4 (2)	O1—C14—C13	118.73 (14)
C5—C4—H4A	120.3	C15—C14—C13	119.39 (13)
C3—C4—H4A	120.3	C16—C15—C20	119.02 (14)
C4—C5—C6	121.1 (2)	C16—C15—C14	121.71 (13)
C4—C5—H5A	119.5	C20—C15—C14	119.26 (14)
C6—C5—H5A	119.5	C17—C16—C15	120.48 (15)
C1—C6—C5	118.54 (16)	C17—C16—H16A	119.8
C1—C6—C7	121.87 (15)	C15—C16—H16A	119.8
C5—C6—C7	119.59 (16)	C16—C17—C18	119.74 (16)
N1—C7—C6	122.09 (15)	C16—C17—H17A	120.1
N1—C7—H7A	119.0	C18—C17—H17A	120.1
C6—C7—H7A	119.0	C19—C18—C17	120.21 (16)
C9—C8—C13	118.64 (14)	C19—C18—H18A	119.9
C9—C8—N1	125.53 (14)	C17—C18—H18A	119.9
C13—C8—N1	115.80 (13)	C18—C19—C20	120.23 (16)
C10—C9—C8	120.82 (15)	C18—C19—H19A	119.9
C10—C9—H9A	119.6	C20—C19—H19A	119.9
C8—C9—H9A	119.6	C19—C20—C15	120.31 (16)
C11—C10—C9	119.56 (15)	C19—C20—H20A	119.8
C11—C10—H10A	120.2	C15—C20—H20A	119.8

O2—C1—C2—C3	−177.1 (2)	C11—C12—C13—C8	0.4 (2)
C6—C1—C2—C3	2.1 (3)	C11—C12—C13—C14	−175.92 (15)
C1—C2—C3—C4	−0.7 (4)	C9—C8—C13—C12	−0.7 (2)
C2—C3—C4—C5	−1.1 (4)	N1—C8—C13—C12	177.30 (13)
C3—C4—C5—C6	1.4 (3)	C9—C8—C13—C14	175.60 (14)
O2—C1—C6—C5	177.45 (16)	N1—C8—C13—C14	−6.4 (2)
C2—C1—C6—C5	−1.7 (3)	C12—C13—C14—O1	82.0 (2)
O2—C1—C6—C7	−1.6 (3)	C8—C13—C14—O1	−94.33 (19)
C2—C1—C6—C7	179.24 (16)	C12—C13—C14—C15	−96.24 (17)
C4—C5—C6—C1	0.0 (3)	C8—C13—C14—C15	87.42 (18)
C4—C5—C6—C7	179.05 (16)	O1—C14—C15—C16	173.85 (16)
C8—N1—C7—C6	178.60 (13)	C13—C14—C15—C16	−8.0 (2)
C1—C6—C7—N1	2.1 (2)	O1—C14—C15—C20	−5.8 (2)
C5—C6—C7—N1	−176.98 (15)	C13—C14—C15—C20	172.40 (14)
C7—N1—C8—C9	−18.6 (2)	C20—C15—C16—C17	0.7 (2)
C7—N1—C8—C13	163.59 (14)	C14—C15—C16—C17	−178.96 (15)
C13—C8—C9—C10	0.2 (2)	C15—C16—C17—C18	−0.4 (3)
N1—C8—C9—C10	−177.59 (15)	C16—C17—C18—C19	−0.2 (3)
C8—C9—C10—C11	0.6 (3)	C17—C18—C19—C20	0.4 (3)
C9—C10—C11—C12	−0.8 (3)	C18—C19—C20—C15	0.0 (3)
C9—C10—C11—Cl1	178.32 (13)	C16—C15—C20—C19	−0.5 (2)
C10—C11—C12—C13	0.3 (3)	C14—C15—C20—C19	179.16 (16)
Cl1—C11—C12—C13	−178.83 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1	0.89 (2)	1.80 (2)	2.6188 (19)	152 (2)
C7—H7A···O1ⁱ	0.93	2.57	3.353 (2)	142
C17—H17A···O1ⁱⁱ	0.93	2.48	3.340 (2)	155

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄ClNO₂
M_r	335.77
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	7.3904 (9), 10.7933 (14), 10.8999 (14)
α, β, γ (°)	73.120 (2), 87.919 (3), 82.953 (3)
V (Å³)	825.71 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.43 × 0.19 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.903, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	9338, 3066, 2481
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.109, 1.03
No. of reflections	3066
No. of parameters	221
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)	0.17, −0.20

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1	0.885 (16)	1.80 (2)	2.6188 (19)	152.2 (17)
C7—H7A···O1ⁱ	0.9300	2.5700	3.353 (2)	142.00
C17—H17A···O1ⁱⁱ	0.9300	2.4800	3.340 (2)	155.00

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

Acknowledgements

MA express his gratitude to the Pakistan Council of Scientific and Industrial Research Laboratories Complex, Karachi, the Department of Chemistry, University of Karachi, and the H·E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, for providing financial support, research facilities and X-ray diffraction facilities, respectively.

References

Aslam, M., Anis, I., Afza, N., Nelofar, A. & Yousuf, S. (2011). Acta Cryst. E67, o3215. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cox, P. J., Kechagias, D. & Kelly, O. (2008). Acta Cryst. B64, 206–216. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fioravanti, R., Biaval, M., Porrettal, G. C., Landolfil, C., Simonetti, N., Villa, A., Conte, E. & Puglia, A. P. (1995). Eur. J. Med. Chem. 30, 123–132. CrossRef CAS Web of Science Google Scholar
Gerdemann, C., Eicken, C. & Krebs, B. (2002). Acc. Chem. Res. 35, 183–191. Web of Science CrossRef PubMed CAS Google Scholar
Khan, K. M., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795–7801. Web of Science CrossRef PubMed CAS Google Scholar
Mallikarjun, S. Y. & Sangamesh, A. P. (1997). Transition Met. Chem. 22, 220–224. Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Samadhiya, S. & Halve, A. (2001). Orient. J. Chem. 17, 119–122. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Solomon, E. I. & Lowery, M. D. (1993). Science, 259, 1575–1581. CrossRef CAS PubMed Web of Science Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vasco-Mendez, N. L., Panneerselvam, K., Rudino-Pinera, E. & Soriano-Garcia, M. (1996). Anal. Sci. 12, 677–678. CAS Google Scholar
Zeb, A. & Yousuf, S. (2011). Acta Cryst. E67, o2801. Web of Science CSD CrossRef IUCr Journals Google Scholar