2-(2,3-Dimethyl­anilino)benzohydrazide

Fun, H.-K.; Chia, T.S.; Elsaman, T.; Attia, M.I.; Abdel-Aziz, H.A.

doi:10.1107/S1600536812032576

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Pages o2527-o2528

https://doi.org/10.1107/S1600536812032576

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2-(2,3-Dimethylanilino)benzohydrazide

Hoong-Kun Fun,^a ^*‡ Tze Shyang Chia,^a Tilal Elsaman,^b Mohamed I. Attia ^b and Hatem A. Abdel-Aziz ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia
^*Correspondence e-mail: hkfun@usm.my

(Received 14 July 2012; accepted 18 July 2012; online 25 July 2012)

In the title compound, C₁₅H₁₇N₃O, the dihedral angle between the benzene rings is 58.05 (9)°. The non-H atoms of the hydrazide group lie in a common plane (r.m.s. deviation = 0.0006 Å) and are close to coplanar with their attached benzene ring [dihedral angle = 8.02 (9)°]. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif in the molecule, and a short intramolecular contact (H⋯H = 1.88 Å) is also observed. In the crystal, molecules are linked by pairs of N—H⋯N hydrogen bonds into inversion dimers. The crystal packing also features C—H⋯π interactions.

Related literature

For the biological activity of fenamates, see: Boschelli et al. (1990 ); Reddy et al. (2010 ); Aboul-Fadl et al. (2011 ). For the synthesis, see: Reddy et al. (2010); Aboul-Fadl et al. (2011). For a related structure, see: Bhat et al. (2012 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For reference bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₅H₁₇N₃O
M_r = 255.32
Triclinic, $[P \overline 1]$
a = 6.9092 (8) Å
b = 6.9609 (7) Å
c = 14.9458 (15) Å
α = 81.562 (2)°
β = 81.328 (2)°
γ = 66.269 (2)°
V = 647.56 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.28 × 0.18 × 0.13 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.977, T_max = 0.989
8491 measured reflections
2218 independent reflections
1826 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.108
S = 1.05
2218 reflections
190 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 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
N2—H1N2⋯N3ⁱ	0.89 (2)	2.29 (2)	3.129 (2)	158.4 (19)
N1—H1N1⋯O1	0.89 (2)	1.90 (2)	2.6667 (19)	143.4 (18)
C11—H11A⋯Cg1ⁱⁱ	0.93	2.58	3.303 (2)	135
C14—H14C⋯Cg1ⁱⁱⁱ	0.96	2.77	3.535 (2)	137
Symmetry codes: (i) -x+3, -y+1, -z; (ii) x+1, y-1, z; (iii) -x+1, -y+1, -z+1.

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/S1600536812032576/hb6900sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812032576/hb6900Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812032576/hb6900Isup3.cml

checkCIF report

Comment top

Mefenamic acid (MFA), N-(2,3-xylyl)anthranilic acid and meclofenamic acid (MCFA) are derivatives of fenamates. They are non-steroidal anti-inflammatory drugs (NSAIDs) used as potent analgesic and anti-inflammatory agents in the treatment of osteoarthritis and rheumatoid arthritis (Boschelli et al., 1990; Reddy et al., 2010; Aboul-Fadl et al., 2011). In view of the importance of the hydrazide of fenamic acid as an active synthon in the synthesis of compounds with biological interests (Reddy et al., 2010; Bhat et al., 2012), we report herein the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The C1–C6 benzene ring makes a dihedral angle of 58.05 (9)° with the C7–C12 benzene ring. The non-H atoms of hydrazide group (O1/N2/N3/C13) lie nearly on a plane [r.m.s. deviation = 0.0006 Å] and are nearly coplanar with the attached C7–C12 benzene ring as indicated by the dihedral angle of 8.02 (9)°. An intramolecular N1—H1N1···O1 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995) in the molecule. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those in a related structure (Bhat et al., 2012).

In the crystal (Fig. 2), the molecules are linked by pairs of intermolecular N2—H1N2···N3 hydrogen bond into inversion dimers. The crystal packing is further stabilized by C—H···π interactions (Table 1), involving Cg1 which is the centroid of C1–C6 ring. A short intramolecular contact [H1N2···H9A = 1.88 Å] is also observed.

Related literature top

For the biological activity of fenamates, see: Boschelli et al. (1990); Reddy et al. (2010); Aboul-Fadl et al. (2011). For the synthesis, see: Reddy et al. (2010); Aboul-Fadl et al. (2011). For a related structure, see: Bhat et al. (2012). For hydrogen-bond motifs, see: Bernstein et al. (1995). For reference bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was prepared by the reaction of the methyl ester of fenamic acid with hydrazine hydrate or with the direct reaction of fenamic acid with hydrazine hydrate under microwave irritation (Reddy et al., 2010; Aboul-Fadl et al., 2011). Brown blocks were grown from the slow evaporation of a methanol solution.

Structure description top

For the biological activity of fenamates, see: Boschelli et al. (1990); Reddy et al. (2010); Aboul-Fadl et al. (2011). For the synthesis, see: Reddy et al. (2010); Aboul-Fadl et al. (2011). For a related structure, see: Bhat et al. (2012). For hydrogen-bond motifs, see: Bernstein et al. (1995). For reference bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for 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 with 50% probability displacement ellipsoids. The dashed line represents the intramolecular N—H···O hydrogen bond.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. The dashed lines represent the hydrogen bonds. For clarity sake, hydrogen atoms not involved in hydrogen bonding have been omitted.

2-(2,3-Dimethylanilino)benzohydrazide top

Crystal data top

C₁₅H₁₇N₃O	Z = 2
M_r = 255.32	F(000) = 272
Triclinic, P1	D_x = 1.309 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9092 (8) Å	Cell parameters from 4059 reflections
b = 6.9609 (7) Å	θ = 2.8–30.3°
c = 14.9458 (15) Å	µ = 0.09 mm⁻¹
α = 81.562 (2)°	T = 100 K
β = 81.328 (2)°	Block, brown
γ = 66.269 (2)°	0.28 × 0.18 × 0.13 mm
V = 647.56 (12) Å³

Data collection top

Bruker APEX DUO CCD diffractometer	2218 independent reflections
Radiation source: fine-focus sealed tube	1826 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
φ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.977, T_max = 0.989	k = −8→8
8491 measured reflections	l = −17→17

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.042P)² + 0.4394P] where P = (F_o² + 2F_c²)/3
2218 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₅H₁₇N₃O	γ = 66.269 (2)°
M_r = 255.32	V = 647.56 (12) Å³
Triclinic, P1	Z = 2
a = 6.9092 (8) Å	Mo Kα radiation
b = 6.9609 (7) Å	µ = 0.09 mm⁻¹
c = 14.9458 (15) Å	T = 100 K
α = 81.562 (2)°	0.28 × 0.18 × 0.13 mm
β = 81.328 (2)°

Data collection top

Bruker APEX DUO CCD diffractometer	2218 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1826 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.989	R_int = 0.028
8491 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.21 e Å⁻³
2218 reflections	Δρ_min = −0.20 e Å⁻³
190 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
O1	0.91711 (19)	0.74672 (18)	0.09083 (8)	0.0228 (3)
N1	0.7359 (2)	0.5409 (2)	0.21691 (10)	0.0232 (4)
N2	1.2514 (3)	0.5701 (2)	0.03071 (10)	0.0228 (4)
N3	1.2742 (2)	0.7493 (2)	−0.01967 (10)	0.0220 (3)
C1	0.4439 (3)	0.4330 (3)	0.27761 (11)	0.0214 (4)
H1A	0.4763	0.3502	0.2296	0.026*
C2	0.2757 (3)	0.4418 (3)	0.34225 (12)	0.0235 (4)
H2A	0.1957	0.3636	0.3385	0.028*
C3	0.2270 (3)	0.5677 (3)	0.41256 (11)	0.0228 (4)
H3A	0.1144	0.5724	0.4562	0.027*
C4	0.3424 (3)	0.6870 (3)	0.41951 (11)	0.0202 (4)
C5	0.5160 (3)	0.6764 (3)	0.35493 (11)	0.0181 (4)
C6	0.5649 (3)	0.5483 (2)	0.28435 (11)	0.0181 (4)
C7	0.9115 (3)	0.3622 (3)	0.19813 (10)	0.0173 (4)
C8	1.0787 (3)	0.3723 (3)	0.13174 (10)	0.0173 (4)
C9	1.2500 (3)	0.1835 (3)	0.11310 (11)	0.0205 (4)
H9A	1.3578	0.1879	0.0684	0.025*
C10	1.2652 (3)	−0.0080 (3)	0.15836 (11)	0.0219 (4)
H10A	1.3814	−0.1305	0.1445	0.026*
C11	1.1052 (3)	−0.0163 (3)	0.22493 (11)	0.0211 (4)
H11A	1.1149	−0.1448	0.2565	0.025*
C12	0.9318 (3)	0.1645 (3)	0.24464 (11)	0.0196 (4)
H12A	0.8258	0.1562	0.2896	0.023*
C13	1.0721 (3)	0.5779 (3)	0.08386 (10)	0.0178 (4)
C14	0.2827 (3)	0.8260 (3)	0.49557 (12)	0.0297 (4)
H14A	0.1620	0.8139	0.5333	0.045*
H14B	0.2479	0.9698	0.4707	0.045*
H14C	0.4002	0.7831	0.5313	0.045*
C15	0.6429 (3)	0.8056 (3)	0.36060 (13)	0.0272 (4)
H15A	0.7813	0.7434	0.3285	0.041*
H15B	0.6571	0.8093	0.4232	0.041*
H15C	0.5712	0.9465	0.3338	0.041*
H1N2	1.370 (3)	0.454 (3)	0.0319 (13)	0.027 (5)*
H1N1	0.756 (3)	0.654 (3)	0.1890 (14)	0.032 (6)*
H2N3	1.204 (3)	0.867 (3)	0.0165 (13)	0.022 (5)*
H1N3	1.188 (4)	0.795 (4)	−0.0667 (17)	0.053 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0206 (7)	0.0180 (6)	0.0261 (6)	−0.0056 (5)	0.0023 (5)	−0.0010 (5)
N1	0.0212 (9)	0.0164 (8)	0.0258 (8)	−0.0049 (6)	0.0064 (6)	0.0002 (6)
N2	0.0184 (9)	0.0202 (8)	0.0263 (8)	−0.0068 (7)	0.0021 (6)	0.0018 (6)
N3	0.0226 (9)	0.0212 (8)	0.0223 (8)	−0.0101 (7)	0.0000 (6)	0.0001 (6)
C1	0.0243 (10)	0.0181 (8)	0.0220 (8)	−0.0077 (7)	−0.0084 (7)	0.0022 (7)
C2	0.0195 (10)	0.0224 (9)	0.0308 (9)	−0.0115 (8)	−0.0090 (7)	0.0073 (7)
C3	0.0121 (9)	0.0278 (10)	0.0222 (9)	−0.0048 (8)	−0.0016 (7)	0.0079 (7)
C4	0.0141 (9)	0.0215 (9)	0.0176 (8)	0.0000 (7)	−0.0042 (6)	0.0024 (6)
C5	0.0130 (9)	0.0170 (8)	0.0217 (8)	−0.0032 (7)	−0.0054 (6)	0.0019 (6)
C6	0.0151 (9)	0.0165 (8)	0.0189 (8)	−0.0039 (7)	−0.0016 (6)	0.0033 (6)
C7	0.0163 (9)	0.0191 (8)	0.0160 (8)	−0.0054 (7)	−0.0034 (6)	−0.0030 (6)
C8	0.0171 (9)	0.0208 (9)	0.0150 (8)	−0.0077 (7)	−0.0043 (6)	−0.0016 (6)
C9	0.0174 (9)	0.0230 (9)	0.0193 (8)	−0.0063 (7)	−0.0004 (7)	−0.0026 (7)
C10	0.0188 (10)	0.0197 (9)	0.0232 (9)	−0.0024 (7)	−0.0039 (7)	−0.0026 (7)
C11	0.0240 (10)	0.0195 (9)	0.0192 (8)	−0.0074 (8)	−0.0077 (7)	0.0026 (6)
C12	0.0192 (9)	0.0225 (9)	0.0172 (8)	−0.0088 (7)	−0.0016 (6)	−0.0002 (6)
C13	0.0176 (9)	0.0218 (9)	0.0155 (8)	−0.0080 (8)	−0.0031 (6)	−0.0034 (6)
C14	0.0242 (11)	0.0312 (10)	0.0246 (9)	−0.0001 (8)	−0.0051 (8)	−0.0039 (8)
C15	0.0206 (10)	0.0234 (9)	0.0385 (11)	−0.0083 (8)	−0.0042 (8)	−0.0051 (8)

Geometric parameters (Å, º) top

O1—C13	1.236 (2)	C5—C15	1.505 (2)
N1—C7	1.372 (2)	C7—C12	1.411 (2)
N1—C6	1.422 (2)	C7—C8	1.422 (2)
N1—H1N1	0.89 (2)	C8—C9	1.401 (2)
N2—C13	1.353 (2)	C8—C13	1.489 (2)
N2—N3	1.412 (2)	C9—C10	1.375 (2)
N2—H1N2	0.89 (2)	C9—H9A	0.9300
N3—H2N3	0.963 (19)	C10—C11	1.385 (2)
N3—H1N3	0.93 (3)	C10—H10A	0.9300
C1—C2	1.382 (3)	C11—C12	1.377 (2)
C1—C6	1.394 (2)	C11—H11A	0.9300
C1—H1A	0.9300	C12—H12A	0.9300
C2—C3	1.383 (3)	C14—H14A	0.9600
C2—H2A	0.9300	C14—H14B	0.9600
C3—C4	1.385 (2)	C14—H14C	0.9600
C3—H3A	0.9300	C15—H15A	0.9600
C4—C5	1.406 (2)	C15—H15B	0.9600
C4—C14	1.503 (2)	C15—H15C	0.9600
C5—C6	1.395 (2)

C7—N1—C6	124.88 (14)	C9—C8—C7	118.05 (15)
C7—N1—H1N1	110.0 (14)	C9—C8—C13	121.02 (15)
C6—N1—H1N1	124.1 (13)	C7—C8—C13	120.93 (15)
C13—N2—N3	123.16 (15)	C10—C9—C8	122.59 (16)
C13—N2—H1N2	121.2 (13)	C10—C9—H9A	118.7
N3—N2—H1N2	115.0 (13)	C8—C9—H9A	118.7
N2—N3—H2N3	108.0 (11)	C9—C10—C11	119.13 (16)
N2—N3—H1N3	109.7 (15)	C9—C10—H10A	120.4
H2N3—N3—H1N3	99.5 (19)	C11—C10—H10A	120.4
C2—C1—C6	119.93 (16)	C12—C11—C10	120.42 (16)
C2—C1—H1A	120.0	C12—C11—H11A	119.8
C6—C1—H1A	120.0	C10—C11—H11A	119.8
C1—C2—C3	119.54 (16)	C11—C12—C7	121.37 (15)
C1—C2—H2A	120.2	C11—C12—H12A	119.3
C3—C2—H2A	120.2	C7—C12—H12A	119.3
C2—C3—C4	121.49 (15)	O1—C13—N2	120.69 (15)
C2—C3—H3A	119.3	O1—C13—C8	124.06 (15)
C4—C3—H3A	119.3	N2—C13—C8	115.25 (15)
C3—C4—C5	119.36 (15)	C4—C14—H14A	109.5
C3—C4—C14	120.26 (16)	C4—C14—H14B	109.5
C5—C4—C14	120.38 (16)	H14A—C14—H14B	109.5
C6—C5—C4	118.89 (15)	C4—C14—H14C	109.5
C6—C5—C15	120.69 (15)	H14A—C14—H14C	109.5
C4—C5—C15	120.39 (15)	H14B—C14—H14C	109.5
C1—C6—C5	120.76 (15)	C5—C15—H15A	109.5
C1—C6—N1	119.64 (15)	C5—C15—H15B	109.5
C5—C6—N1	119.57 (15)	H15A—C15—H15B	109.5
N1—C7—C12	120.95 (15)	C5—C15—H15C	109.5
N1—C7—C8	120.68 (15)	H15A—C15—H15C	109.5
C12—C7—C8	118.37 (15)	H15B—C15—H15C	109.5

C6—C1—C2—C3	0.9 (2)	N1—C7—C8—C9	−177.64 (15)
C1—C2—C3—C4	0.5 (3)	C12—C7—C8—C9	2.9 (2)
C2—C3—C4—C5	−1.5 (2)	N1—C7—C8—C13	2.7 (2)
C2—C3—C4—C14	178.65 (15)	C12—C7—C8—C13	−176.72 (14)
C3—C4—C5—C6	1.2 (2)	C7—C8—C9—C10	−2.1 (2)
C14—C4—C5—C6	−178.98 (15)	C13—C8—C9—C10	177.53 (15)
C3—C4—C5—C15	179.57 (16)	C8—C9—C10—C11	0.2 (3)
C14—C4—C5—C15	−0.6 (2)	C9—C10—C11—C12	0.9 (2)
C2—C1—C6—C5	−1.2 (2)	C10—C11—C12—C7	0.0 (2)
C2—C1—C6—N1	−179.12 (15)	N1—C7—C12—C11	178.61 (16)
C4—C5—C6—C1	0.1 (2)	C8—C7—C12—C11	−2.0 (2)
C15—C5—C6—C1	−178.22 (15)	N3—N2—C13—O1	−0.2 (2)
C4—C5—C6—N1	178.07 (14)	N3—N2—C13—C8	−179.91 (14)
C15—C5—C6—N1	−0.3 (2)	C9—C8—C13—O1	172.87 (15)
C7—N1—C6—C1	−61.6 (2)	C7—C8—C13—O1	−7.5 (2)
C7—N1—C6—C5	120.45 (18)	C9—C8—C13—N2	−7.4 (2)
C6—N1—C7—C12	2.0 (3)	C7—C8—C13—N2	172.23 (14)
C6—N1—C7—C8	−177.41 (15)

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
N2—H1N2···N3ⁱ	0.89 (2)	2.29 (2)	3.129 (2)	158.4 (19)
N1—H1N1···O1	0.89 (2)	1.90 (2)	2.6667 (19)	143.4 (18)
C11—H11A···Cg1ⁱⁱ	0.93	2.58	3.303 (2)	135
C14—H14C···Cg1ⁱⁱⁱ	0.96	2.77	3.535 (2)	137

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇N₃O
M_r	255.32
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.9092 (8), 6.9609 (7), 14.9458 (15)
α, β, γ (°)	81.562 (2), 81.328 (2), 66.269 (2)
V (Å³)	647.56 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.18 × 0.13

Data collection
Diffractometer	Bruker APEX DUO CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.977, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	8491, 2218, 1826
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.108, 1.05
No. of reflections	2218
No. of parameters	190
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

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 C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N3ⁱ	0.89 (2)	2.29 (2)	3.129 (2)	158.4 (19)
N1—H1N1···O1	0.89 (2)	1.90 (2)	2.6667 (19)	143.4 (18)
C11—H11A···Cg1ⁱⁱ	0.93	2.58	3.303 (2)	135
C14—H14C···Cg1ⁱⁱⁱ	0.96	2.77	3.535 (2)	137

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSC thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). TSC thanks the Malaysian government and USM for the award of a Research Fellowship. The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University, for funding and facilities.

References

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