{5-Chloro-2-[(4-nitro­benzyl­idene)amino]­phen­yl}(phen­yl)methanone

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

doi:10.1107/S1600536811046162

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3215

https://doi.org/10.1107/S1600536811046162

Open

access

{5-Chloro-2-[(4-nitrobenzylidene)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 Labs. 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: dr.sammer.yousuf@gmail.com

(Received 26 October 2011; accepted 2 November 2011; online 5 November 2011)

The molecule of the title Schiff base compound, C₂₀H₁₃ClN₂O₃, assumes an E configuration about the C=N bond. The aromatic rings of the nitrobenzene and chlorobenzene groups are twisted by 13.89 (13)° and form dihedral angles of 76.38 (13) and 84.64 (13)°, respectively, with the phenyl ring. In the crystal, molecules are linked into chains parallel to the b axis by C—H⋯π interactions.

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: Zeb & Yousuf (2011 ); Cox et al. (2008 ); Vasco-Mendez et al. (1996 ).

Experimental

Crystal data

C₂₀H₁₃ClN₂O₃
M_r = 364.77
Monoclinic, P 2₁ /n
a = 7.231 (2) Å
b = 20.235 (6) Å
c = 11.942 (4) Å
β = 98.030 (6)°
V = 1730.1 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 273 K
0.22 × 0.13 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.948, T_max = 0.974
9867 measured reflections
3117 independent reflections
2059 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.125
S = 1.06
3117 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19A⋯Cg1ⁱ	0.93	2.68	3.538 (3)	154
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536811046162/rz2660sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046162/rz2660Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811046162/rz2660Isup3.cml

checkCIF report

Comment top

Schiff bases are well known reaction products of aldehyde/ketone functionalities with amines and are considered as important ligands in coordination chemistry. They are also well known to possess a wide range of biological activities including antifungal, antiinflammatory, anti-HIV, antibacterial, herbicidal, antiproliferative, cytotoxic, anticonvulsant and anticancer 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 and crystallized during our ongoing research on bioactive compounds.

The structure of title compound (Fig. 1) is composed of three aromatic rings A–C (C1-C6, C8-C13 and C15-C20) with dihedral angles of 76.38 (13)°, 84.64 (13)° and 13.89 (13)° between the A/B, A/C and B/C planes, respectively. The azomethine C═N double bond adopts an E configuration, with a C13–N1–C14–C15 torsion angle of 177.1 (2)°. The bond lengths and angles are similar to those observed in other structurally related compounds (Cox et al., 2008; Vasco-Mendez et al., 1996; Zeb & Yousuf, 2011). The bond length of the azomethine double bond is 1.249 (3)Å. In the crystal structure (Fig. 2), the molecules are arranged into chains parallel to the b axis by C—H···π interactions (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: 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 4-nitrobenzaldehyde (1 mol) and 2-amino-5-chlorobenzophenone (1 mol) in ethanol (50 ml) along with 3 drops of conc. H₂SO₄ for 5 h at 70 °C. After cooling down to room temperature, the crystalline product was collected by filtration, washed with methanol and dried to afford the title compound in 85% yield. Recrystallization from methanol 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: 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 30% probability level.
	Fig. 2. Crystal packing of the title compound viewed along the a axis.

{5-Chloro-2-[(4-nitrobenzylidene)amino]phenyl}(phenyl)methanone top

Crystal data top

C₂₀H₁₃ClN₂O₃	F(000) = 752
M_r = 364.77	D_x = 1.400 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1927 reflections
a = 7.231 (2) Å	θ = 2.7–22.4°
b = 20.235 (6) Å	µ = 0.24 mm⁻¹
c = 11.942 (4) Å	T = 273 K
β = 98.030 (6)°	Block, yellow
V = 1730.1 (9) Å³	0.22 × 0.13 × 0.11 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3117 independent reflections
Radiation source: fine-focus sealed tube	2059 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scan	θ_max = 25.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
T_min = 0.948, T_max = 0.974	k = −24→24
9867 measured reflections	l = −14→14

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0442P)² + 0.6878P] where P = (F_o² + 2F_c²)/3
3117 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₀H₁₃ClN₂O₃	V = 1730.1 (9) Å³
M_r = 364.77	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.231 (2) Å	µ = 0.24 mm⁻¹
b = 20.235 (6) Å	T = 273 K
c = 11.942 (4) Å	0.22 × 0.13 × 0.11 mm
β = 98.030 (6)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3117 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2059 reflections with I > 2σ(I)
T_min = 0.948, T_max = 0.974	R_int = 0.034
9867 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.06	Δρ_max = 0.17 e Å⁻³
3117 reflections	Δρ_min = −0.22 e Å⁻³
235 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	0.19880 (13)	0.14369 (6)	0.09091 (6)	0.0991 (4)
O1	0.5383 (3)	0.18026 (11)	0.52750 (17)	0.0748 (6)
O2	0.2903 (3)	−0.18427 (11)	1.03849 (16)	0.0729 (6)
O3	0.3022 (4)	−0.08484 (12)	1.09952 (18)	0.1055 (9)
N1	0.2719 (3)	0.02909 (11)	0.54984 (17)	0.0546 (6)
N2	0.2951 (3)	−0.12485 (13)	1.02346 (19)	0.0610 (6)
C1	0.0800 (4)	0.16884 (13)	0.6054 (2)	0.0559 (7)
H1B	0.0152	0.1594	0.5344	0.067*
C2	−0.0173 (4)	0.18077 (15)	0.6959 (3)	0.0705 (9)
H2A	−0.1472	0.1797	0.6854	0.085*
C3	0.0798 (5)	0.19418 (15)	0.8012 (3)	0.0682 (9)
H3A	0.0151	0.2016	0.8620	0.082*
C4	0.2711 (5)	0.19659 (15)	0.8168 (2)	0.0631 (8)
H4A	0.3357	0.2058	0.8879	0.076*
C5	0.3672 (4)	0.18538 (13)	0.7273 (2)	0.0535 (7)
H5A	0.4970	0.1875	0.7382	0.064*
C6	0.2730 (4)	0.17095 (11)	0.6210 (2)	0.0442 (6)
C7	0.3806 (4)	0.15890 (12)	0.5257 (2)	0.0472 (6)
C8	0.2958 (3)	0.11941 (13)	0.42535 (19)	0.0444 (6)
C9	0.2807 (4)	0.14706 (15)	0.3181 (2)	0.0563 (7)
H9A	0.3118	0.1912	0.3093	0.068*
C10	0.2197 (4)	0.10903 (17)	0.2252 (2)	0.0590 (8)
C11	0.1768 (4)	0.04369 (17)	0.2359 (2)	0.0614 (8)
H11A	0.1375	0.0184	0.1719	0.074*
C12	0.1918 (4)	0.01582 (14)	0.3409 (2)	0.0610 (8)
H12A	0.1618	−0.0285	0.3480	0.073*
C13	0.2515 (4)	0.05276 (13)	0.43751 (19)	0.0462 (6)
C14	0.2730 (4)	−0.03103 (13)	0.5735 (2)	0.0488 (7)
H14A	0.2657	−0.0619	0.5154	0.059*
C15	0.2857 (3)	−0.05421 (12)	0.6908 (2)	0.0448 (6)
C16	0.3020 (4)	−0.01050 (14)	0.7803 (2)	0.0566 (7)
H16A	0.3102	0.0346	0.7667	0.068*
C17	0.3062 (4)	−0.03285 (14)	0.8895 (2)	0.0581 (8)
H17A	0.3180	−0.0034	0.9498	0.070*
C18	0.2927 (4)	−0.09993 (13)	0.9074 (2)	0.0478 (6)
C19	0.2786 (4)	−0.14440 (13)	0.8209 (2)	0.0531 (7)
H19A	0.2719	−0.1895	0.8351	0.064*
C20	0.2745 (4)	−0.12143 (13)	0.7120 (2)	0.0528 (7)
H20A	0.2642	−0.1512	0.6522	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0832 (7)	0.1653 (10)	0.0474 (4)	−0.0118 (6)	0.0041 (4)	0.0365 (5)
O1	0.0597 (14)	0.0966 (17)	0.0717 (14)	−0.0256 (12)	0.0214 (11)	−0.0183 (11)
O2	0.0972 (18)	0.0613 (14)	0.0608 (13)	−0.0026 (13)	0.0128 (11)	0.0164 (10)
O3	0.186 (3)	0.0809 (17)	0.0499 (13)	0.0053 (18)	0.0163 (15)	−0.0056 (12)
N1	0.0755 (18)	0.0418 (13)	0.0458 (12)	0.0014 (12)	0.0063 (11)	0.0035 (9)
N2	0.0676 (17)	0.0663 (17)	0.0484 (14)	0.0002 (14)	0.0057 (12)	0.0003 (12)
C1	0.0523 (19)	0.0556 (18)	0.0602 (17)	−0.0004 (14)	0.0091 (14)	−0.0060 (13)
C2	0.059 (2)	0.072 (2)	0.085 (2)	0.0021 (16)	0.0268 (18)	−0.0072 (17)
C3	0.089 (3)	0.063 (2)	0.0586 (19)	0.0127 (18)	0.0333 (18)	0.0035 (14)
C4	0.075 (2)	0.069 (2)	0.0452 (16)	0.0092 (17)	0.0094 (15)	0.0049 (13)
C5	0.0576 (18)	0.0553 (17)	0.0476 (15)	0.0049 (14)	0.0077 (13)	0.0037 (12)
C6	0.0493 (17)	0.0368 (14)	0.0471 (14)	−0.0004 (12)	0.0083 (12)	0.0031 (11)
C7	0.0489 (17)	0.0454 (16)	0.0477 (15)	−0.0028 (13)	0.0080 (12)	0.0039 (11)
C8	0.0408 (15)	0.0512 (16)	0.0424 (14)	0.0023 (12)	0.0108 (11)	0.0033 (11)
C9	0.0538 (18)	0.0645 (19)	0.0509 (17)	−0.0034 (15)	0.0085 (13)	0.0164 (14)
C10	0.0458 (18)	0.091 (2)	0.0409 (15)	0.0045 (16)	0.0086 (13)	0.0125 (15)
C11	0.0555 (19)	0.085 (2)	0.0417 (15)	0.0083 (17)	0.0012 (13)	−0.0088 (14)
C12	0.075 (2)	0.0539 (18)	0.0529 (17)	0.0018 (15)	0.0046 (15)	−0.0083 (13)
C13	0.0501 (17)	0.0494 (16)	0.0397 (13)	0.0052 (13)	0.0081 (12)	0.0005 (11)
C14	0.0530 (18)	0.0473 (17)	0.0476 (15)	0.0010 (13)	0.0122 (12)	−0.0015 (12)
C15	0.0436 (16)	0.0422 (15)	0.0494 (15)	0.0013 (12)	0.0098 (12)	0.0021 (11)
C16	0.071 (2)	0.0431 (16)	0.0543 (17)	−0.0057 (14)	0.0019 (14)	0.0019 (12)
C17	0.072 (2)	0.0481 (17)	0.0514 (16)	−0.0011 (15)	0.0002 (14)	−0.0074 (13)
C18	0.0462 (16)	0.0528 (17)	0.0433 (14)	0.0020 (13)	0.0027 (12)	0.0047 (12)
C19	0.0625 (19)	0.0424 (16)	0.0556 (16)	−0.0003 (13)	0.0130 (14)	0.0037 (12)
C20	0.0646 (19)	0.0447 (16)	0.0500 (15)	0.0019 (14)	0.0111 (13)	−0.0013 (12)

Geometric parameters (Å, º) top

Cl1—C10	1.738 (3)	C8—C13	1.398 (3)
O1—C7	1.217 (3)	C9—C10	1.371 (4)
O2—N2	1.217 (3)	C9—H9A	0.9300
O3—N2	1.213 (3)	C10—C11	1.368 (4)
N1—C14	1.249 (3)	C11—C12	1.366 (4)
N1—C13	1.413 (3)	C11—H11A	0.9300
N2—C18	1.472 (3)	C12—C13	1.392 (4)
C1—C6	1.383 (4)	C12—H12A	0.9300
C1—C2	1.390 (4)	C14—C15	1.468 (3)
C1—H1B	0.9300	C14—H14A	0.9300
C2—C3	1.379 (4)	C15—C16	1.379 (4)
C2—H2A	0.9300	C15—C20	1.388 (3)
C3—C4	1.370 (4)	C16—C17	1.377 (4)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.372 (4)	C17—C18	1.380 (4)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.386 (3)	C18—C19	1.364 (4)
C5—H5A	0.9300	C19—C20	1.377 (3)
C6—C7	1.485 (3)	C19—H19A	0.9300
C7—C8	1.498 (3)	C20—H20A	0.9300
C8—C9	1.388 (3)

C14—N1—C13	122.8 (2)	C11—C10—Cl1	119.0 (2)
O3—N2—O2	123.3 (2)	C9—C10—Cl1	119.8 (3)
O3—N2—C18	118.0 (3)	C12—C11—C10	119.6 (3)
O2—N2—C18	118.7 (2)	C12—C11—H11A	120.2
C6—C1—C2	120.1 (3)	C10—C11—H11A	120.2
C6—C1—H1B	119.9	C11—C12—C13	121.0 (3)
C2—C1—H1B	119.9	C11—C12—H12A	119.5
C3—C2—C1	119.6 (3)	C13—C12—H12A	119.5
C3—C2—H2A	120.2	C12—C13—C8	118.7 (2)
C1—C2—H2A	120.2	C12—C13—N1	125.8 (2)
C4—C3—C2	120.5 (3)	C8—C13—N1	115.5 (2)
C4—C3—H3A	119.8	N1—C14—C15	121.7 (2)
C2—C3—H3A	119.8	N1—C14—H14A	119.2
C3—C4—C5	120.0 (3)	C15—C14—H14A	119.2
C3—C4—H4A	120.0	C16—C15—C20	119.2 (2)
C5—C4—H4A	120.0	C16—C15—C14	121.4 (2)
C4—C5—C6	120.7 (3)	C20—C15—C14	119.3 (2)
C4—C5—H5A	119.6	C17—C16—C15	120.7 (3)
C6—C5—H5A	119.6	C17—C16—H16A	119.6
C1—C6—C5	119.1 (2)	C15—C16—H16A	119.6
C1—C6—C7	121.3 (2)	C18—C17—C16	118.5 (2)
C5—C6—C7	119.6 (2)	C18—C17—H17A	120.7
O1—C7—C6	121.2 (2)	C16—C17—H17A	120.7
O1—C7—C8	118.8 (2)	C19—C18—C17	122.1 (2)
C6—C7—C8	120.0 (2)	C19—C18—N2	118.5 (2)
C9—C8—C13	119.7 (2)	C17—C18—N2	119.4 (2)
C9—C8—C7	119.6 (2)	C18—C19—C20	118.8 (3)
C13—C8—C7	120.4 (2)	C18—C19—H19A	120.6
C10—C9—C8	119.7 (3)	C20—C19—H19A	120.6
C10—C9—H9A	120.2	C19—C20—C15	120.6 (2)
C8—C9—H9A	120.2	C19—C20—H20A	119.7
C11—C10—C9	121.2 (3)	C15—C20—H20A	119.7

C6—C1—C2—C3	−0.5 (4)	C11—C12—C13—N1	179.9 (3)
C1—C2—C3—C4	0.8 (5)	C9—C8—C13—C12	−0.4 (4)
C2—C3—C4—C5	−0.2 (5)	C7—C8—C13—C12	−173.2 (2)
C3—C4—C5—C6	−0.6 (4)	C9—C8—C13—N1	179.7 (2)
C2—C1—C6—C5	−0.3 (4)	C7—C8—C13—N1	7.0 (3)
C2—C1—C6—C7	−179.5 (2)	C14—N1—C13—C12	14.4 (4)
C4—C5—C6—C1	0.9 (4)	C14—N1—C13—C8	−165.8 (3)
C4—C5—C6—C7	−179.9 (2)	C13—N1—C14—C15	−177.1 (2)
C1—C6—C7—O1	156.5 (3)	N1—C14—C15—C16	−1.8 (4)
C5—C6—C7—O1	−22.7 (4)	N1—C14—C15—C20	176.0 (3)
C1—C6—C7—C8	−24.0 (4)	C20—C15—C16—C17	−0.4 (4)
C5—C6—C7—C8	156.8 (2)	C14—C15—C16—C17	177.4 (2)
O1—C7—C8—C9	−57.3 (4)	C15—C16—C17—C18	−0.4 (4)
C6—C7—C8—C9	123.1 (3)	C16—C17—C18—C19	1.1 (4)
O1—C7—C8—C13	115.5 (3)	C16—C17—C18—N2	−179.4 (2)
C6—C7—C8—C13	−64.1 (3)	O3—N2—C18—C19	−177.9 (3)
C13—C8—C9—C10	1.0 (4)	O2—N2—C18—C19	2.2 (4)
C7—C8—C9—C10	173.8 (2)	O3—N2—C18—C17	2.6 (4)
C8—C9—C10—C11	−1.3 (4)	O2—N2—C18—C17	−177.2 (3)
C8—C9—C10—Cl1	179.5 (2)	C17—C18—C19—C20	−1.1 (4)
C9—C10—C11—C12	1.0 (4)	N2—C18—C19—C20	179.4 (2)
Cl1—C10—C11—C12	−179.7 (2)	C18—C19—C20—C15	0.4 (4)
C10—C11—C12—C13	−0.4 (5)	C16—C15—C20—C19	0.4 (4)
C11—C12—C13—C8	0.1 (4)	C14—C15—C20—C19	−177.5 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···Cg1ⁱ	0.93	2.68	3.538 (3)	154

Symmetry code: (i) −x+1/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₃ClN₂O₃
M_r	364.77
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	7.231 (2), 20.235 (6), 11.942 (4)
β (°)	98.030 (6)
V (Å³)	1730.1 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.22 × 0.13 × 0.11

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.948, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	9867, 3117, 2059
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.125, 1.06
No. of reflections	3117
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.22

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

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···Cg1ⁱ	0.93	2.68	3.538 (3)	154

Symmetry code: (i) −x+1/2, y−1/2, −z+3/2.

References

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., Biava, M., Porretta, G. C., Landolfi, C., Simonetti, N., Villa, A., Conte, E. & Porta-Puglia, A. (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

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 12| December 2011| Page o3215

https://doi.org/10.1107/S1600536811046162

Open

access