3-(4-Chloro­phen­yl)-1-phenyl-1H-pyrazole-4-carbaldehyde

Fun, H.-K.; Arshad, S.; Malladi, S.; Selvam, R.; Isloor, A.M.

doi:10.1107/S1600536811023713

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages o1783-o1784

doi:10.1107/S1600536811023713

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3-(4-Chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde

Hoong-Kun Fun,^a ^*‡ Suhana Arshad,^a Shridhar Malladi,^b R. Selvam ^b and Arun M. Isloor ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 15 June 2011; accepted 17 June 2011; online 25 June 2011)

In the title compound, C₁₆H₁₁ClN₂O, the chloro-substituted phenyl ring is disordered over two positions with refined site occupancies of 0.503 (2) and 0.497 (2). The dihedral angle between the pyrazole and phenyl rings is 7.93 (7)°. The pyrazole ring also forms dihedral angles of 24.43 (9)° and 28.67 (9)° with the disordered chloro-substituted benzene ring. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds, generating R₂¹(7) and R₂²(10) ring motifs. π–π interactions between the pyrazole and phenyl rings [centroid–centroid distance = 3.758 (1) Å] further stabilize the crystal structure.

Related literature

For related pharmacological literature, see: Karci & Karci (2008 ); Isloor et al. (2000 ); Kalluraya et al. (2004 ); Isloor et al. (2009 ); Comber et al. (1992 ). For the experimental preparation, see: Vora et al. (2009 ). For reference bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₆H₁₁ClN₂O
M_r = 282.72
Monoclinic, P 2₁ /c
a = 16.0429 (4) Å
b = 4.8585 (1) Å
c = 16.7960 (4) Å
β = 96.581 (1)°
V = 1300.53 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 100 K
0.55 × 0.16 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.858, T_max = 0.979
26528 measured reflections
3859 independent reflections
3302 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.098
S = 1.03
3859 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1ⁱ	0.95	2.42	3.3545 (18)	167
C7—H7A⋯O1ⁱ	0.95	2.33	3.2684 (16)	169
Symmetry code: (i) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811023713/wn2437sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811023713/wn2437Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811023713/wn2437Isup3.cml

checkCIF report

Comment top

Heterocyclic compounds have been gaining more importance in recent years due to their pharmacological activities. Nitrogen-, sulfur-, oxygen-containing five- or six-membered heterocyclic compounds are of enormous significance in the field of drug discovery process. Pyrazoles are important compounds that have many derivatives with a wide range of interesting properties, such as antipyretic, hypoglycemic, sedative-hypnotic (Karci & Karci, 2008), analgesic (Isloor et al., 2000), anti-inflammatory (Kalluraya et al., 2004) and antimicrobial activities (Isloor et al., 2009). Much attention was paid to pyrazole as a potential antimicrobial agent after the discovery of the natural pyrazole C-glycoside and pyrazofurin which demonstrated a broad spectrum of antimicrobial activity (Comber et al., 1992).

The molecular structure is shown in Fig 1. The chloro-substituted phenyl ring (C10–C15) is disordered over two positions with refined site occupancies of 0.503 (2) and 0.497 (2). The dihedral angle between the pyrazole ring (N1/N2/C7–C9) and the phenyl ring (C1–C6) is 7.93 (7)°. The pyrazole ring also forms dihedral angles of 24.43 (9)° and 28.67 (9)° with the disordered chloro-substituted phenyl rings (C10–C15) and (C10–C11X–C12X–C13–C14X–C15X), respectively. The bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal packing (Fig. 2), the intermolecular C1—H1A···O1 and C7—H7A···O1 hydrogen bonds (Table 1) link the molecules to form dimers, generating R¹₂(7) and R²₂(10) ring motifs (Bernstein et al., 1995). π–π interactions between the pyrazole and phenyl rings further stabilize the crystal structure; [Cg1···Cg2 = 3.7579 (8) Å, where Cg1 and Cg2 are the centroids of the rings N1/N2/C7–C9 and C1–C6, respectively; symmetry code: x, y - 1, z].

Related literature top

For related pharmacological literature, see: Karci & Karci (2008); Isloor et al. (2000); Kalluraya et al. (2004); Isloor et al. (2009); Comber et al. (1992). For the experimental preparation, see: Vora et al. (2009). For reference bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Phosphoryl chloride (5 ml) was added dropwise to cold N,N- dimethylformamide (DMF) (15 ml) with continuous stirring at 273–278 K for about 30 min. 4-Chloroacetophenone phenylhydrazone (3.66 g, 15 mmol) was separately dissolved in 5 ml of DMF and was added dropwise to the former cold mixture with continuous stirring at 273–278 K for an hour. The resulting mixture was further stirred at 323–333 K for 5–6 h and cooled to room temperature. The crude product was poured into crushed ice, resulting in a white precipitate. The precipitate was filtered, washed with water and recrystallized from ethanol. Yield: 3.7 g, 87.4%. M.p.: 413–415 K (Vora et al., 2009).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. Both disordered components are shown.
	Fig. 2. The crystal packing of the title compound. Dashed lines represent the intermolecular hydrogen bonds. Only the major disordered components are shown.

3-(4-Chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde top

Crystal data top

C₁₆H₁₁ClN₂O	F(000) = 584
M_r = 282.72	D_x = 1.444 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9960 reflections
a = 16.0429 (4) Å	θ = 2.4–30.2°
b = 4.8585 (1) Å	µ = 0.29 mm⁻¹
c = 16.7960 (4) Å	T = 100 K
β = 96.581 (1)°	Needle, colourless
V = 1300.53 (5) Å³	0.55 × 0.16 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3859 independent reflections
Radiation source: fine-focus sealed tube	3302 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ϕ and ω scans	θ_max = 30.2°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −22→22
T_min = 0.858, T_max = 0.979	k = −6→6
26528 measured reflections	l = −20→23

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0397P)² + 0.6665P] where P = (F_o² + 2F_c²)/3
3859 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₆H₁₁ClN₂O	V = 1300.53 (5) Å³
M_r = 282.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.0429 (4) Å	µ = 0.29 mm⁻¹
b = 4.8585 (1) Å	T = 100 K
c = 16.7960 (4) Å	0.55 × 0.16 × 0.08 mm
β = 96.581 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3859 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3302 reflections with I > 2σ(I)
T_min = 0.858, T_max = 0.979	R_int = 0.057
26528 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.03	Δρ_max = 0.36 e Å⁻³
3859 reflections	Δρ_min = −0.35 e Å⁻³
218 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	Occ. (<1)
Cl1	−0.055017 (18)	−0.04423 (7)	0.181350 (19)	0.02215 (9)
O1	0.43582 (6)	−0.2143 (2)	0.07840 (6)	0.0270 (2)
N1	0.32027 (6)	0.4298 (2)	−0.06319 (6)	0.0180 (2)
N2	0.24330 (7)	0.4223 (2)	−0.03471 (7)	0.0190 (2)
C1	0.41332 (9)	0.6604 (3)	−0.14732 (9)	0.0241 (3)
H1A	0.4596	0.5576	−0.1225	0.029*
C2	0.42428 (9)	0.8515 (3)	−0.20713 (9)	0.0248 (3)
H2A	0.4785	0.8781	−0.2234	0.030*
C3	0.35726 (9)	1.0028 (3)	−0.24314 (8)	0.0238 (3)
H3A	0.3654	1.1322	−0.2840	0.029*
C4	0.27791 (9)	0.9645 (3)	−0.21919 (8)	0.0276 (3)
H4A	0.2318	1.0693	−0.2434	0.033*
C5	0.26568 (8)	0.7734 (3)	−0.15994 (8)	0.0245 (3)
H5A	0.2114	0.7462	−0.1439	0.029*
C6	0.33339 (8)	0.6232 (3)	−0.12461 (7)	0.0183 (2)
C7	0.37382 (8)	0.2434 (3)	−0.02733 (7)	0.0181 (2)
H7A	0.4300	0.2126	−0.0379	0.022*
C8	0.33170 (7)	0.1040 (3)	0.02808 (7)	0.0171 (2)
C9	0.24994 (7)	0.2247 (3)	0.02049 (7)	0.0167 (2)
C10	0.17600 (7)	0.1594 (3)	0.06219 (7)	0.0160 (2)
C13	0.03440 (7)	0.0390 (3)	0.13674 (7)	0.0158 (2)
C11	0.16431 (15)	−0.0971 (5)	0.09304 (15)	0.0177 (5)	0.503 (2)
H11A	0.2047	−0.2365	0.0871	0.021*	0.503 (2)
C12	0.09495 (15)	−0.1604 (5)	0.13298 (15)	0.0176 (5)	0.503 (2)
H12A	0.0897	−0.3359	0.1569	0.021*	0.503 (2)
C14	0.04106 (15)	0.2993 (5)	0.10535 (15)	0.0187 (5)	0.503 (2)
H14A	−0.0012	0.4336	0.1098	0.022*	0.503 (2)
C15	0.11108 (15)	0.3605 (5)	0.06696 (15)	0.0181 (5)	0.503 (2)
H15A	0.1161	0.5370	0.0436	0.022*	0.503 (2)
C11X	0.18437 (14)	0.0503 (5)	0.14160 (14)	0.0155 (5)	0.497 (2)
H11B	0.2384	0.0184	0.1695	0.019*	0.497 (2)
C12X	0.11256 (15)	−0.0091 (5)	0.17791 (14)	0.0159 (5)	0.497 (2)
H12B	0.1174	−0.0822	0.2307	0.019*	0.497 (2)
C14X	0.02656 (14)	0.1474 (5)	0.05831 (14)	0.0169 (5)	0.497 (2)
H14B	−0.0273	0.1799	0.0301	0.020*	0.497 (2)
C15X	0.09871 (15)	0.2059 (5)	0.02300 (14)	0.0173 (5)	0.497 (2)
H15B	0.0937	0.2799	−0.0297	0.021*	0.497 (2)
C16	0.36592 (8)	−0.1175 (4)	0.07881 (8)	0.0274 (3)
H16A	0.3312	−0.1937	0.1154	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01577 (14)	0.02598 (17)	0.02634 (17)	−0.00049 (11)	0.00943 (11)	0.00063 (13)
O1	0.0174 (4)	0.0356 (6)	0.0282 (5)	0.0042 (4)	0.0033 (4)	0.0034 (4)
N1	0.0180 (5)	0.0166 (5)	0.0209 (5)	−0.0017 (4)	0.0091 (4)	−0.0018 (4)
N2	0.0182 (5)	0.0174 (5)	0.0232 (5)	−0.0007 (4)	0.0105 (4)	−0.0014 (4)
C1	0.0240 (6)	0.0170 (6)	0.0336 (7)	0.0012 (5)	0.0140 (5)	0.0014 (5)
C2	0.0267 (6)	0.0191 (6)	0.0316 (7)	−0.0023 (5)	0.0161 (5)	−0.0004 (6)
C3	0.0300 (7)	0.0229 (7)	0.0197 (6)	−0.0059 (6)	0.0082 (5)	0.0001 (5)
C4	0.0233 (6)	0.0360 (8)	0.0232 (6)	−0.0034 (6)	0.0016 (5)	0.0054 (6)
C5	0.0194 (6)	0.0331 (8)	0.0215 (6)	−0.0046 (5)	0.0041 (5)	0.0029 (6)
C6	0.0223 (6)	0.0149 (6)	0.0193 (6)	−0.0035 (5)	0.0089 (4)	−0.0032 (5)
C7	0.0170 (5)	0.0178 (6)	0.0205 (6)	−0.0017 (5)	0.0061 (4)	−0.0035 (5)
C8	0.0149 (5)	0.0190 (6)	0.0182 (5)	−0.0022 (4)	0.0048 (4)	−0.0039 (5)
C9	0.0164 (5)	0.0165 (6)	0.0180 (5)	−0.0024 (4)	0.0054 (4)	−0.0041 (5)
C10	0.0155 (5)	0.0162 (6)	0.0171 (5)	−0.0009 (4)	0.0053 (4)	−0.0024 (4)
C13	0.0136 (5)	0.0179 (6)	0.0166 (5)	−0.0007 (4)	0.0046 (4)	−0.0015 (4)
C11	0.0130 (10)	0.0192 (12)	0.0209 (12)	0.0028 (9)	0.0021 (8)	0.0000 (9)
C12	0.0169 (10)	0.0169 (12)	0.0192 (11)	−0.0001 (9)	0.0030 (8)	0.0023 (9)
C14	0.0164 (10)	0.0198 (12)	0.0205 (12)	0.0042 (9)	0.0049 (9)	−0.0010 (10)
C15	0.0189 (11)	0.0156 (11)	0.0207 (11)	0.0008 (9)	0.0059 (9)	−0.0002 (10)
C11X	0.0127 (10)	0.0170 (11)	0.0166 (11)	0.0012 (9)	0.0013 (8)	−0.0008 (9)
C12X	0.0161 (10)	0.0176 (12)	0.0145 (10)	0.0003 (9)	0.0037 (8)	0.0018 (9)
C14X	0.0127 (10)	0.0201 (12)	0.0176 (11)	0.0003 (9)	0.0005 (8)	−0.0011 (10)
C15X	0.0170 (11)	0.0197 (12)	0.0152 (11)	−0.0001 (9)	0.0020 (8)	0.0017 (9)
C16	0.0160 (6)	0.0436 (9)	0.0232 (6)	0.0018 (6)	0.0047 (5)	0.0092 (6)

Geometric parameters (Å, º) top

Cl1—C13	1.7405 (12)	C10—C15X	1.355 (3)
O1—C16	1.2168 (16)	C10—C11	1.371 (3)
N1—C7	1.3427 (17)	C10—C11X	1.427 (3)
N1—N2	1.3749 (13)	C10—C15	1.437 (3)
N1—C6	1.4287 (16)	C13—C14	1.379 (3)
N2—C9	1.3301 (16)	C13—C12	1.379 (3)
C1—C6	1.3909 (17)	C13—C12X	1.381 (3)
C1—C2	1.3935 (19)	C13—C14X	1.411 (3)
C1—H1A	0.9500	C11—C12	1.398 (3)
C2—C3	1.383 (2)	C11—H11A	0.9500
C2—H2A	0.9500	C12—H12A	0.9500
C3—C4	1.3908 (18)	C14—C15	1.390 (3)
C3—H3A	0.9500	C14—H14A	0.9500
C4—C5	1.391 (2)	C15—H15A	0.9500
C4—H4A	0.9500	C11X—C12X	1.394 (3)
C5—C6	1.3844 (19)	C11X—H11B	0.9500
C5—H5A	0.9500	C12X—H12B	0.9500
C7—C8	1.3877 (17)	C14X—C15X	1.389 (3)
C7—H7A	0.9500	C14X—H14B	0.9500
C8—C9	1.4292 (16)	C15X—H15B	0.9500
C8—C16	1.441 (2)	C16—H16A	0.9500
C9—C10	1.4795 (16)

C7—N1—N2	112.33 (10)	C15—C10—C9	120.41 (14)
C7—N1—C6	128.90 (10)	C14—C13—C12	122.76 (16)
N2—N1—C6	118.77 (10)	C14—C13—C12X	103.95 (17)
C9—N2—N1	104.97 (10)	C12—C13—C12X	45.55 (15)
C6—C1—C2	118.74 (13)	C14—C13—C14X	45.84 (15)
C6—C1—H1A	120.6	C12—C13—C14X	101.97 (16)
C2—C1—H1A	120.6	C12X—C13—C14X	120.63 (16)
C3—C2—C1	120.88 (12)	C14—C13—Cl1	118.80 (13)
C3—C2—H2A	119.6	C12—C13—Cl1	118.43 (13)
C1—C2—H2A	119.6	C12X—C13—Cl1	119.40 (13)
C2—C3—C4	119.58 (13)	C14X—C13—Cl1	119.94 (12)
C2—C3—H3A	120.2	C10—C11—C12	122.2 (2)
C4—C3—H3A	120.2	C10—C11—H11A	118.9
C3—C4—C5	120.33 (13)	C12—C11—H11A	118.9
C3—C4—H4A	119.8	C13—C12—C11	118.1 (2)
C5—C4—H4A	119.8	C13—C12—H12A	120.9
C6—C5—C4	119.36 (12)	C11—C12—H12A	120.9
C6—C5—H5A	120.3	C13—C14—C15	118.4 (2)
C4—C5—H5A	120.3	C13—C14—H14A	120.8
C5—C6—C1	121.10 (12)	C15—C14—H14A	120.8
C5—C6—N1	118.87 (11)	C14—C15—C10	120.7 (2)
C1—C6—N1	120.02 (12)	C14—C15—H15A	119.7
N1—C7—C8	107.12 (11)	C10—C15—H15A	119.7
N1—C7—H7A	126.4	C12X—C11X—C10	119.5 (2)
C8—C7—H7A	126.4	C12X—C11X—H11B	120.3
C7—C8—C9	104.61 (11)	C10—C11X—H11B	120.3
C7—C8—C16	125.38 (11)	C13—C12X—C11X	119.6 (2)
C9—C8—C16	129.99 (11)	C13—C12X—H12B	120.2
N2—C9—C8	110.96 (10)	C11X—C12X—H12B	120.2
N2—C9—C10	118.70 (11)	C15X—C14X—C13	119.0 (2)
C8—C9—C10	130.32 (11)	C15X—C14X—H14B	120.5
C15X—C10—C11	100.24 (17)	C13—C14X—H14B	120.5
C15X—C10—C11X	119.92 (16)	C10—C15X—C14X	121.3 (2)
C11—C10—C11X	46.48 (15)	C10—C15X—H15B	119.3
C11—C10—C15	117.75 (16)	C14X—C15X—H15B	119.3
C11X—C10—C15	101.05 (15)	O1—C16—C8	125.03 (13)
C15X—C10—C9	118.24 (14)	O1—C16—H16A	117.5
C11—C10—C9	121.72 (14)	C8—C16—H16A	117.5
C11X—C10—C9	121.83 (13)

C7—N1—N2—C9	0.05 (14)	C9—C10—C11—C12	179.58 (18)
C6—N1—N2—C9	179.65 (11)	C14—C13—C12—C11	−2.3 (3)
C6—C1—C2—C3	0.3 (2)	C12X—C13—C12—C11	−79.1 (3)
C1—C2—C3—C4	0.2 (2)	C14X—C13—C12—C11	42.4 (3)
C2—C3—C4—C5	−0.6 (2)	Cl1—C13—C12—C11	176.41 (17)
C3—C4—C5—C6	0.5 (2)	C10—C11—C12—C13	4.0 (3)
C4—C5—C6—C1	0.1 (2)	C12—C13—C14—C15	1.3 (3)
C4—C5—C6—N1	179.29 (13)	C12X—C13—C14—C15	47.0 (3)
C2—C1—C6—C5	−0.5 (2)	C14X—C13—C14—C15	−72.4 (2)
C2—C1—C6—N1	−179.69 (12)	Cl1—C13—C14—C15	−177.43 (17)
C7—N1—C6—C5	172.00 (13)	C13—C14—C15—C10	−1.7 (3)
N2—N1—C6—C5	−7.51 (17)	C15X—C10—C15—C14	78.7 (3)
C7—N1—C6—C1	−8.8 (2)	C11—C10—C15—C14	3.2 (3)
N2—N1—C6—C1	171.72 (12)	C11X—C10—C15—C14	−43.1 (3)
N2—N1—C7—C8	−0.27 (14)	C9—C10—C15—C14	179.34 (18)
C6—N1—C7—C8	−179.81 (12)	C15X—C10—C11X—C12X	0.4 (3)
N1—C7—C8—C9	0.36 (13)	C11—C10—C11X—C12X	−74.3 (3)
N1—C7—C8—C16	178.86 (13)	C15—C10—C11X—C12X	43.6 (3)
N1—N2—C9—C8	0.19 (13)	C9—C10—C11X—C12X	−179.63 (18)
N1—N2—C9—C10	−178.74 (10)	C14—C13—C12X—C11X	−46.5 (3)
C7—C8—C9—N2	−0.34 (14)	C12—C13—C12X—C11X	76.0 (3)
C16—C8—C9—N2	−178.75 (14)	C14X—C13—C12X—C11X	0.1 (3)
C7—C8—C9—C10	178.42 (12)	Cl1—C13—C12X—C11X	178.26 (17)
C16—C8—C9—C10	0.0 (2)	C10—C11X—C12X—C13	−0.2 (3)
N2—C9—C10—C15X	28.1 (2)	C14—C13—C14X—C15X	79.2 (3)
C8—C9—C10—C15X	−150.62 (17)	C12—C13—C14X—C15X	−45.2 (3)
N2—C9—C10—C11	152.77 (16)	C12X—C13—C14X—C15X	−0.2 (3)
C8—C9—C10—C11	−25.9 (2)	Cl1—C13—C14X—C15X	−178.35 (18)
N2—C9—C10—C11X	−151.92 (16)	C11—C10—C15X—C14X	44.8 (3)
C8—C9—C10—C11X	29.4 (2)	C11X—C10—C15X—C14X	−0.5 (3)
N2—C9—C10—C15	−23.2 (2)	C15—C10—C15X—C14X	−74.7 (3)
C8—C9—C10—C15	158.14 (16)	C9—C10—C15X—C14X	179.5 (2)
C15X—C10—C11—C12	−47.8 (3)	C13—C14X—C15X—C10	0.4 (4)
C11X—C10—C11—C12	74.0 (3)	C7—C8—C16—O1	−1.5 (2)
C15—C10—C11—C12	−4.4 (3)	C9—C8—C16—O1	176.61 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1ⁱ	0.95	2.42	3.3545 (18)	167
C7—H7A···O1ⁱ	0.95	2.33	3.2684 (16)	169

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁ClN₂O
M_r	282.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	16.0429 (4), 4.8585 (1), 16.7960 (4)
β (°)	96.581 (1)
V (Å³)	1300.53 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.55 × 0.16 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.858, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	26528, 3859, 3302
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.708

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.098, 1.03
No. of reflections	3859
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.35

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1ⁱ	0.95	2.42	3.3545 (18)	167
C7—H7A···O1ⁱ	0.95	2.33	3.2684 (16)	169

Symmetry code: (i) −x+1, −y, −z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). SA thanks the Malaysian Government and USM for the award of a research scholarship. AMI thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India for a Young Scientist award.

References

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