N-(4-Chloro­phen­yl)-2,2-diphenyl­acetamide

Fun, H.-K.; Loh, W.-S.; Nayak, P.S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812032965

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Pages o2556-o2557

https://doi.org/10.1107/S1600536812032965

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N-(4-Chlorophenyl)-2,2-diphenylacetamide

Hoong-Kun Fun,^a ^*‡ Wan-Sin Loh,^a § Prakash S Nayak,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P.A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 17 July 2012; accepted 20 July 2012; online 25 July 2012)

In the title compound, C₂₀H₁₆ClNO, an S(6) ring motif is formed via an intramolecular C—H⋯O hydrogen bond. The chloro-substituted benzene ring is almost perpendicular to the benzene rings, forming dihedral angles of 87.33 (9) and 88.69 (9)°. The dihedral angle between the benzene rings is 87.17 (9)°. In the crystal, molecules are linked into chains parallel to the c axis by intermolecular N—H⋯O hydrogen bonds. The crystal packing also features weak C—H⋯π interactions involving the chloro-substituted ring.

Related literature

For related structures, see: Fun et al. (2012a ,b ,c ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₀H₁₆ClNO
M_r = 321.79
Monoclinic, P 2₁ /c
a = 10.2147 (2) Å
b = 17.8203 (4) Å
c = 9.5730 (2) Å
β = 114.019 (1)°
V = 1591.68 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 100 K
0.49 × 0.27 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.890, T_max = 0.954
14326 measured reflections
3639 independent reflections
3091 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.103
S = 1.09
3639 reflections
212 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.84 (2)	2.07 (2)	2.8598 (19)	157 (2)
C1—H1A⋯O1	0.95	2.58	3.202 (3)	123
C4—H4A⋯Cg1ⁱⁱ	0.95	2.93	3.415 (2)	113
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-1, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

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: https://doi.org/10.1107/S1600536812032965/rz2793sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812032965/rz2793Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812032965/rz2793Isup3.cml

checkCIF report

Comment top

In continuation of our work on the synthesis of amides (Fun et al., 2012a,b,c) we report herein the crystal structure of the title compound.

In the title compound, Fig. 1, an S(6) ring motif (Bernstein et al., 1995) is formed via intramolecular C1—H1A···O1 hydrogen bond (Table 1). The chloro-substituted benzene ring (C15–C20) is almost perpendicular to the benzene rings (C1–C6, C7–C12) forming dihedral angles of 87.33 (9) and 88.69 (9)°, respectively. The dihedral angle formed by the benzene rings is 87.17 (9)°. Bond lengths (Allen et al., 1987) and angles are within the normal ranges. In the crystal packing (Fig. 2), the molecules are linked into chains parallel the c axis by intermolecular N1—H1N1···O1 hydrogen bonds (Table 1). The crystal packing is further stabilized by weak C—H···π interactions (Table 1) involving the chloro-substituted ring.

Related literature top

For related structures, see: Fun et al. (2012a,b,c). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Diphenylacetic acid (0.212 g, 1 mmol), 4-chloroaniline (0.127 g, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) were dissolved in dichloromethane (20 ml). The mixture was stirred in presence of triethylamine at 273 K for about 3 h. The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring, which was extracted thrice with dichloromethane. The organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound. Single crystals were grown from N,N-dimethylformamide by the slow evaporation method. M.p.: 463–465 K.

Structure description top

In continuation of our work on the synthesis of amides (Fun et al., 2012a,b,c) we report herein the crystal structure of the title compound.

For related structures, see: Fun et al. (2012a,b,c). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

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 50% probability displacement ellipsoids. The dashed line indicates the intramolecular hydrogen bond.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

N-(4-Chlorophenyl)-2,2-diphenylacetamide top

Crystal data top

C₂₀H₁₆ClNO	F(000) = 672
M_r = 321.79	D_x = 1.343 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8307 reflections
a = 10.2147 (2) Å	θ = 2.2–32.2°
b = 17.8203 (4) Å	µ = 0.24 mm⁻¹
c = 9.5730 (2) Å	T = 100 K
β = 114.019 (1)°	Block, colourless
V = 1591.68 (6) Å³	0.49 × 0.27 × 0.19 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3639 independent reflections
Radiation source: fine-focus sealed tube	3091 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
φ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
T_min = 0.890, T_max = 0.954	k = −21→23
14326 measured reflections	l = −12→12

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0323P)² + 1.4338P] where P = (F_o² + 2F_c²)/3
3639 reflections	(Δ/σ)_max = 0.001
212 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₀H₁₆ClNO	V = 1591.68 (6) Å³
M_r = 321.79	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.2147 (2) Å	µ = 0.24 mm⁻¹
b = 17.8203 (4) Å	T = 100 K
c = 9.5730 (2) Å	0.49 × 0.27 × 0.19 mm
β = 114.019 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3639 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3091 reflections with I > 2σ(I)
T_min = 0.890, T_max = 0.954	R_int = 0.028
14326 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.30 e Å⁻³
3639 reflections	Δρ_min = −0.28 e Å⁻³
212 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
Cl1	1.15388 (5)	0.49276 (3)	1.29695 (5)	0.02582 (13)
O1	0.61313 (13)	0.26955 (7)	0.78711 (13)	0.0207 (3)
N1	0.64271 (15)	0.29804 (8)	1.03055 (16)	0.0164 (3)
H1N1	0.614 (2)	0.2863 (12)	1.098 (3)	0.027 (6)*
C1	0.2968 (2)	0.32265 (11)	0.7336 (2)	0.0228 (4)
H1A	0.3761	0.3418	0.7169	0.027*
C2	0.1669 (2)	0.36130 (12)	0.6756 (2)	0.0315 (5)
H2A	0.1578	0.4064	0.6194	0.038*
C3	0.0508 (2)	0.33385 (12)	0.6999 (3)	0.0352 (5)
H3A	−0.0377	0.3602	0.6609	0.042*
C4	0.0645 (2)	0.26804 (12)	0.7810 (2)	0.0310 (5)
H4A	−0.0149	0.2491	0.7977	0.037*
C5	0.19353 (19)	0.22950 (11)	0.8381 (2)	0.0237 (4)
H5A	0.2017	0.1842	0.8932	0.028*
C6	0.31158 (18)	0.25666 (10)	0.81530 (19)	0.0179 (4)
C7	0.37110 (18)	0.12810 (10)	0.6510 (2)	0.0182 (4)
H7A	0.3131	0.1676	0.5905	0.022*
C8	0.37547 (19)	0.05950 (10)	0.5837 (2)	0.0211 (4)
H8A	0.3202	0.0525	0.4774	0.025*
C9	0.45962 (19)	0.00140 (10)	0.6702 (2)	0.0213 (4)
H9A	0.4622	−0.0453	0.6235	0.026*
C10	0.54027 (19)	0.01183 (10)	0.8258 (2)	0.0206 (4)
H10A	0.5984	−0.0277	0.8859	0.025*
C11	0.53563 (18)	0.08021 (10)	0.8931 (2)	0.0184 (4)
H11A	0.5907	0.0870	0.9996	0.022*
C12	0.45162 (17)	0.13905 (10)	0.80713 (19)	0.0158 (3)
C13	0.45186 (17)	0.21313 (10)	0.88570 (18)	0.0156 (3)
H13A	0.4669	0.2009	0.9931	0.019*
C14	0.57806 (17)	0.26222 (10)	0.89552 (19)	0.0155 (3)
C15	0.76050 (17)	0.34768 (10)	1.08061 (19)	0.0160 (3)
C16	0.84756 (18)	0.36106 (10)	1.0026 (2)	0.0192 (4)
H16A	0.8252	0.3391	0.9052	0.023*
C17	0.96742 (18)	0.40692 (10)	1.0687 (2)	0.0206 (4)
H17A	1.0280	0.4158	1.0170	0.025*
C18	0.99832 (18)	0.43946 (10)	1.2094 (2)	0.0199 (4)
C19	0.90983 (19)	0.42853 (10)	1.2855 (2)	0.0209 (4)
H19A	0.9307	0.4521	1.3812	0.025*
C20	0.79109 (18)	0.38303 (10)	1.2206 (2)	0.0193 (4)
H20A	0.7295	0.3757	1.2717	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0203 (2)	0.0244 (2)	0.0292 (3)	−0.00523 (17)	0.00640 (18)	−0.00464 (19)
O1	0.0268 (6)	0.0253 (7)	0.0134 (6)	−0.0066 (5)	0.0119 (5)	−0.0035 (5)
N1	0.0188 (7)	0.0221 (8)	0.0115 (7)	−0.0028 (6)	0.0095 (6)	−0.0009 (6)
C1	0.0239 (9)	0.0212 (9)	0.0236 (9)	0.0012 (7)	0.0100 (7)	−0.0002 (8)
C2	0.0332 (11)	0.0235 (10)	0.0336 (12)	0.0061 (8)	0.0093 (9)	0.0002 (9)
C3	0.0239 (10)	0.0314 (12)	0.0446 (13)	0.0058 (8)	0.0080 (9)	−0.0130 (10)
C4	0.0225 (9)	0.0328 (11)	0.0396 (12)	−0.0054 (8)	0.0148 (9)	−0.0146 (10)
C5	0.0244 (9)	0.0228 (10)	0.0262 (10)	−0.0050 (7)	0.0126 (8)	−0.0062 (8)
C6	0.0197 (8)	0.0191 (9)	0.0154 (8)	−0.0015 (7)	0.0078 (7)	−0.0064 (7)
C7	0.0217 (8)	0.0189 (9)	0.0155 (8)	0.0005 (7)	0.0090 (7)	0.0022 (7)
C8	0.0264 (9)	0.0232 (10)	0.0154 (8)	−0.0031 (7)	0.0101 (7)	−0.0035 (7)
C9	0.0268 (9)	0.0177 (9)	0.0248 (9)	−0.0017 (7)	0.0161 (8)	−0.0033 (7)
C10	0.0228 (9)	0.0185 (9)	0.0234 (9)	0.0021 (7)	0.0125 (7)	0.0046 (7)
C11	0.0202 (8)	0.0214 (9)	0.0146 (8)	−0.0019 (7)	0.0081 (7)	0.0004 (7)
C12	0.0178 (8)	0.0170 (8)	0.0163 (8)	−0.0030 (6)	0.0107 (7)	−0.0006 (7)
C13	0.0199 (8)	0.0185 (9)	0.0101 (8)	−0.0016 (7)	0.0079 (6)	0.0005 (7)
C14	0.0183 (8)	0.0161 (8)	0.0133 (8)	0.0016 (6)	0.0077 (6)	0.0010 (7)
C15	0.0169 (8)	0.0166 (8)	0.0136 (8)	0.0009 (6)	0.0053 (6)	0.0006 (7)
C16	0.0231 (9)	0.0217 (9)	0.0147 (8)	−0.0005 (7)	0.0095 (7)	−0.0012 (7)
C17	0.0202 (8)	0.0229 (9)	0.0205 (9)	−0.0012 (7)	0.0102 (7)	−0.0001 (8)
C18	0.0164 (8)	0.0168 (9)	0.0226 (9)	−0.0002 (7)	0.0041 (7)	−0.0003 (7)
C19	0.0230 (9)	0.0224 (9)	0.0160 (9)	0.0009 (7)	0.0068 (7)	−0.0054 (7)
C20	0.0206 (8)	0.0228 (9)	0.0168 (9)	0.0008 (7)	0.0099 (7)	−0.0023 (7)

Geometric parameters (Å, º) top

Cl1—C18	1.7451 (18)	C8—H8A	0.9500
O1—C14	1.2349 (19)	C9—C10	1.390 (3)
N1—C14	1.349 (2)	C9—H9A	0.9500
N1—C15	1.411 (2)	C10—C11	1.388 (3)
N1—H1N1	0.84 (2)	C10—H10A	0.9500
C1—C6	1.386 (3)	C11—C12	1.392 (2)
C1—C2	1.395 (3)	C11—H11A	0.9500
C1—H1A	0.9500	C12—C13	1.519 (2)
C2—C3	1.387 (3)	C13—C14	1.529 (2)
C2—H2A	0.9500	C13—H13A	1.0000
C3—C4	1.382 (3)	C15—C16	1.395 (2)
C3—H3A	0.9500	C15—C20	1.397 (2)
C4—C5	1.386 (3)	C16—C17	1.392 (2)
C4—H4A	0.9500	C16—H16A	0.9500
C5—C6	1.396 (2)	C17—C18	1.380 (3)
C5—H5A	0.9500	C17—H17A	0.9500
C6—C13	1.524 (2)	C18—C19	1.386 (2)
C7—C8	1.391 (3)	C19—C20	1.379 (2)
C7—C12	1.396 (2)	C19—H19A	0.9500
C7—H7A	0.9500	C20—H20A	0.9500
C8—C9	1.385 (3)

C14—N1—C15	129.75 (14)	C10—C11—C12	121.05 (16)
C14—N1—H1N1	115.6 (15)	C10—C11—H11A	119.5
C15—N1—H1N1	114.4 (15)	C12—C11—H11A	119.5
C6—C1—C2	120.71 (18)	C11—C12—C7	118.73 (16)
C6—C1—H1A	119.6	C11—C12—C13	119.04 (15)
C2—C1—H1A	119.6	C7—C12—C13	122.23 (15)
C3—C2—C1	119.9 (2)	C12—C13—C6	114.31 (14)
C3—C2—H2A	120.0	C12—C13—C14	111.05 (13)
C1—C2—H2A	120.0	C6—C13—C14	110.69 (14)
C4—C3—C2	119.74 (19)	C12—C13—H13A	106.8
C4—C3—H3A	120.1	C6—C13—H13A	106.8
C2—C3—H3A	120.1	C14—C13—H13A	106.8
C3—C4—C5	120.29 (19)	O1—C14—N1	123.99 (16)
C3—C4—H4A	119.9	O1—C14—C13	122.31 (15)
C5—C4—H4A	119.9	N1—C14—C13	113.66 (14)
C4—C5—C6	120.65 (19)	C16—C15—C20	119.63 (16)
C4—C5—H5A	119.7	C16—C15—N1	124.52 (15)
C6—C5—H5A	119.7	C20—C15—N1	115.82 (15)
C1—C6—C5	118.67 (17)	C17—C16—C15	119.43 (16)
C1—C6—C13	123.22 (15)	C17—C16—H16A	120.3
C5—C6—C13	118.08 (16)	C15—C16—H16A	120.3
C8—C7—C12	120.19 (17)	C18—C17—C16	120.00 (16)
C8—C7—H7A	119.9	C18—C17—H17A	120.0
C12—C7—H7A	119.9	C16—C17—H17A	120.0
C9—C8—C7	120.61 (17)	C17—C18—C19	120.99 (16)
C9—C8—H8A	119.7	C17—C18—Cl1	119.93 (14)
C7—C8—H8A	119.7	C19—C18—Cl1	119.04 (14)
C8—C9—C10	119.58 (17)	C20—C19—C18	119.22 (16)
C8—C9—H9A	120.2	C20—C19—H19A	120.4
C10—C9—H9A	120.2	C18—C19—H19A	120.4
C11—C10—C9	119.83 (17)	C19—C20—C15	120.65 (16)
C11—C10—H10A	120.1	C19—C20—H20A	119.7
C9—C10—H10A	120.1	C15—C20—H20A	119.7

C6—C1—C2—C3	0.2 (3)	C5—C6—C13—C12	72.2 (2)
C1—C2—C3—C4	−0.3 (3)	C1—C6—C13—C14	16.8 (2)
C2—C3—C4—C5	0.1 (3)	C5—C6—C13—C14	−161.46 (15)
C3—C4—C5—C6	0.3 (3)	C15—N1—C14—O1	−1.8 (3)
C2—C1—C6—C5	0.2 (3)	C15—N1—C14—C13	−179.66 (16)
C2—C1—C6—C13	−178.09 (17)	C12—C13—C14—O1	43.3 (2)
C4—C5—C6—C1	−0.4 (3)	C6—C13—C14—O1	−84.76 (19)
C4—C5—C6—C13	177.91 (16)	C12—C13—C14—N1	−138.80 (15)
C12—C7—C8—C9	−0.1 (3)	C6—C13—C14—N1	93.11 (17)
C7—C8—C9—C10	0.1 (3)	C14—N1—C15—C16	−9.8 (3)
C8—C9—C10—C11	0.1 (3)	C14—N1—C15—C20	172.23 (17)
C9—C10—C11—C12	−0.3 (3)	C20—C15—C16—C17	2.8 (3)
C10—C11—C12—C7	0.2 (2)	N1—C15—C16—C17	−175.13 (16)
C10—C11—C12—C13	−179.13 (15)	C15—C16—C17—C18	−0.8 (3)
C8—C7—C12—C11	0.0 (2)	C16—C17—C18—C19	−1.4 (3)
C8—C7—C12—C13	179.30 (15)	C16—C17—C18—Cl1	176.51 (14)
C11—C12—C13—C6	−149.59 (15)	C17—C18—C19—C20	1.5 (3)
C7—C12—C13—C6	31.1 (2)	Cl1—C18—C19—C20	−176.42 (14)
C11—C12—C13—C14	84.30 (18)	C18—C19—C20—C15	0.6 (3)
C7—C12—C13—C14	−95.00 (18)	C16—C15—C20—C19	−2.7 (3)
C1—C6—C13—C12	−109.50 (18)	N1—C15—C20—C19	175.40 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.84 (2)	2.07 (2)	2.8598 (19)	157 (2)
C1—H1A···O1	0.95	2.58	3.202 (3)	123
C4—H4A···Cg1ⁱⁱ	0.95	2.93	3.415 (2)	113

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆ClNO
M_r	321.79
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.2147 (2), 17.8203 (4), 9.5730 (2)
β (°)	114.019 (1)
V (Å³)	1591.68 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.49 × 0.27 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.890, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	14326, 3639, 3091
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.103, 1.09
No. of reflections	3639
No. of parameters	212
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.28

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.84 (2)	2.07 (2)	2.8598 (19)	157 (2)
C1—H1A···O1	0.9500	2.5800	3.202 (3)	123.00
C4—H4A···Cg1ⁱⁱ	0.9500	2.93	3.415 (2)	113.00

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7581-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the post of Research Officer under the Research University Grant (1001/PFIZIK/811160). BN thanks the UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP–DRS-Phase 1 programme.

References

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