5-Ethyl-2-(4-fluoro­phen­yl)-4-phen­oxy-1H-pyrazol-3(2H)-one

Shahani, T.; Fun, H.-K.; Ragavan, R.V.; Vijayakumar, V.; Venkatesh, M.

doi:10.1107/S1600536811000754

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o475

doi:10.1107/S1600536811000754

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5-Ethyl-2-(4-fluorophenyl)-4-phenoxy-1H-pyrazol-3(2H)-one

Tara Shahani,^a Hoong-Kun Fun,^a ^*‡ R. Venkat Ragavan,^b V. Vijayakumar ^b and M. Venkatesh ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
^*Correspondence e-mail: hkfun@usm.my

(Received 5 January 2011; accepted 6 January 2011; online 22 January 2011)

In the title compound, C₁₇H₁₅FN₂O₂, the essentially planar pyrazole ring [maximum deviation = 0.026 (1) Å] makes dihedral angles of 72.06 (7) and 33.05 (7)°, with the phenyl and fluorobenzene rings, respectively. The dihedral angle between the two six-membered rings is 87.88 (7)°. In the crystal, intermolecular N—H⋯O and C—H⋯F hydrogen bonds link the molecules into layers lying parallel to the bc plane.

Related literature

For pyrazole derivatives and their microbial activity, see: Ragavan et al. (2009 , 2010 ). For the synthesis, see: Ragavan et al. (2009). For related structures, see: Shahani et al. (2009 , 2010a ,b ). 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

C₁₇H₁₅FN₂O₂
M_r = 298.31
Monoclinic, P 2₁ /c
a = 15.332 (2) Å
b = 8.6833 (14) Å
c = 11.6066 (19) Å
β = 109.916 (3)°
V = 1452.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.55 × 0.14 × 0.08 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.947, T_max = 0.992
12927 measured reflections
4247 independent reflections
3207 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.119
S = 1.05
4247 reflections
204 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2ⁱ	0.899 (18)	1.803 (18)	2.6865 (14)	167.1 (16)
C11—H11A⋯F1ⁱⁱ	0.93	2.52	3.3441 (16)	147
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: 10.1107/S1600536811000754/hb5788sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000754/hb5788Isup2.hkl

checkCIF report

Comment top

Antibacterial and antifungal activities of the azoles are most widely studied and some of them are in clinical practice as anti-microbial agents. However, the azole-resistant strain had led to the development of new antimicrobial compounds. In particular pyrazole derivatives are extensively studied and used as antimicrobial agents. Pyrazole is an important class of heterocyclic compounds and many pyrazole derivatives are reported to have the broad spectrum of biological properties, such as anti-inflammatory, antifungal, herbicidal,anti-tumour, cytotoxic, molecular modelling, and antiviral activities. Pyrazole derivatives also act as antiangiogenic agents, A3 adenosine receptor antagonists, neuropeptide YY5 receptor antagonists, kinase inhibitor for treatment of type 2 diabetes, hyperlipidemia, obesity, and thrombopiotinmimetics. Recently urea derivatives of pyrazoles have been reported as potent inhibitors of p38 kinase. Since the high electronegativity of halogens (particularly chlorine and fluorine) in the aromatic part of the drug molecules play an important role in enhancing their biological activity, we are interested to have 4-fluoro or 4-chloro substitution in the aryls of 1,5-diaryl pyrazoles. As part of our on-going research aiming the synthesis of new antimicrobial compounds, we have reported the synthesis of novel pyrazole derivatives and their microbial activities (Ragavan et al., 2009; 2010). The structure of the title compound, (I), is presented here.

In the title compound (Fig. 1), the molecule consists of two phenyl (C10—C15 and C1—C6) and one pyrazole (N1/N2/C7—C9) rings, all rings are essentially planar. The pyrazole ring (maximum deviation of 0.026 (1) Å at atom N1) makes dihedral angles of 72.06 (7) and 33.05 (7)°, with phenyl (C10—C15) and fluoro substituted phenyl (C1—C6) rings, respectively. The dihedral angle between the two six-membered rings,(C1—C6) and (C10—C15), is 87.88 (7)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the closely related structures (Shahani et al.,2009; 2010a,b).

In the crystal (Fig. 2), intermolecular N2–H1N2···O2 and C11–H11A···F1 (Table 1) hydrogen bonds link the molecules into two-dimensional arrays parallel to the bc plane.

Related literature top

For pyrazole derivatives and their microbial activity, see: Ragavan et al. (2009, 2010). For the synthesis, see: Ragavan et al. (2009). For related structures, see: Shahani et al. (2009, 2010a,b). 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

The compound was synthesized using the literature method (Ragavan et al.,2009) and recrystallized using an ethanol-chloroform 1:1 mixture to yield colourless needles of (I). Yield: 61%. M.p.: 441 K.

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 (I), showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of (I), viewed along b axis. Intermolecular hydrogen bonds linked the molecules into two-dimensional arrays parallel to the bc plane. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

5-Ethyl-2-(4-fluorophenyl)-4-phenoxy-1H-pyrazol-3(2H)-one top

Crystal data top

C₁₇H₁₅FN₂O₂	F(000) = 624
M_r = 298.31	D_x = 1.364 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2971 reflections
a = 15.332 (2) Å	θ = 3.0–33.0°
b = 8.6833 (14) Å	µ = 0.10 mm⁻¹
c = 11.6066 (19) Å	T = 100 K
β = 109.916 (3)°	Needle, colourless
V = 1452.8 (4) Å³	0.55 × 0.14 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD diffractometer	4247 independent reflections
Radiation source: fine-focus sealed tube	3207 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 30.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→20
T_min = 0.947, T_max = 0.992	k = −12→9
12927 measured reflections	l = −16→16

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) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.047P)² + 0.4776P] where P = (F_o² + 2F_c²)/3
4247 reflections	(Δ/σ)_max < 0.001
204 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₇H₁₅FN₂O₂	V = 1452.8 (4) Å³
M_r = 298.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.332 (2) Å	µ = 0.10 mm⁻¹
b = 8.6833 (14) Å	T = 100 K
c = 11.6066 (19) Å	0.55 × 0.14 × 0.08 mm
β = 109.916 (3)°

Data collection top

Bruker APEXII DUO CCD diffractometer	4247 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3207 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.992	R_int = 0.036
12927 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.34 e Å⁻³
4247 reflections	Δρ_min = −0.24 e Å⁻³
204 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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
F1	0.77686 (5)	0.90535 (11)	0.09196 (7)	0.0332 (2)
O1	0.22938 (6)	0.55499 (11)	0.07275 (8)	0.0226 (2)
O2	0.40598 (6)	0.72722 (11)	0.20071 (7)	0.0243 (2)
N1	0.41488 (7)	0.72695 (13)	0.00442 (8)	0.0187 (2)
N2	0.36358 (7)	0.66422 (13)	−0.10812 (9)	0.0192 (2)
C1	0.55898 (8)	0.70430 (15)	−0.03872 (10)	0.0191 (2)
H1A	0.5320	0.6289	−0.0969	0.023*
C2	0.64946 (9)	0.75124 (16)	−0.01831 (11)	0.0215 (3)
H2A	0.6836	0.7098	−0.0634	0.026*
C3	0.68736 (8)	0.86072 (16)	0.07039 (11)	0.0222 (3)
C4	0.63952 (9)	0.92659 (15)	0.13937 (11)	0.0215 (3)
H4A	0.6677	0.9992	0.1994	0.026*
C5	0.54850 (8)	0.88198 (15)	0.11691 (10)	0.0200 (3)
H5A	0.5142	0.9261	0.1607	0.024*
C6	0.50869 (8)	0.77049 (14)	0.02820 (10)	0.0172 (2)
C7	0.37115 (8)	0.69697 (15)	0.08861 (10)	0.0187 (2)
C8	0.28708 (8)	0.62287 (15)	0.01905 (10)	0.0190 (2)
C9	0.28418 (8)	0.60586 (15)	−0.09962 (10)	0.0190 (2)
C10	0.14644 (8)	0.62813 (16)	0.06414 (11)	0.0204 (3)
C11	0.10224 (9)	0.56911 (18)	0.14043 (11)	0.0254 (3)
H11A	0.1284	0.4881	0.1933	0.030*
C12	0.01814 (10)	0.6329 (2)	0.13677 (13)	0.0337 (4)
H12A	−0.0120	0.5947	0.1880	0.040*
C13	−0.02094 (10)	0.7526 (2)	0.05755 (14)	0.0378 (4)
H13A	−0.0772	0.7950	0.0554	0.045*
C14	0.02428 (10)	0.8092 (2)	−0.01883 (13)	0.0330 (3)
H14A	−0.0023	0.8892	−0.0727	0.040*
C15	0.10888 (9)	0.74771 (17)	−0.01581 (11)	0.0252 (3)
H15A	0.1394	0.7863	−0.0665	0.030*
C16	0.21135 (9)	0.53400 (17)	−0.20637 (11)	0.0246 (3)
H16A	0.1673	0.6127	−0.2491	0.030*
H16B	0.1781	0.4578	−0.1764	0.030*
C17	0.25005 (10)	0.45693 (18)	−0.29685 (12)	0.0282 (3)
H17A	0.2009	0.4051	−0.3590	0.042*
H17B	0.2968	0.3836	−0.2542	0.042*
H17C	0.2769	0.5336	−0.3342	0.042*
H1N2	0.3689 (12)	0.706 (2)	−0.1764 (16)	0.035 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0199 (4)	0.0497 (6)	0.0311 (4)	−0.0092 (4)	0.0103 (3)	−0.0079 (4)
O1	0.0193 (4)	0.0301 (5)	0.0232 (4)	0.0039 (4)	0.0136 (3)	0.0076 (4)
O2	0.0251 (4)	0.0367 (6)	0.0138 (4)	0.0009 (4)	0.0100 (3)	−0.0019 (3)
N1	0.0179 (5)	0.0274 (6)	0.0124 (4)	−0.0018 (4)	0.0071 (4)	−0.0017 (4)
N2	0.0192 (5)	0.0275 (6)	0.0120 (4)	−0.0024 (4)	0.0067 (4)	−0.0009 (4)
C1	0.0208 (5)	0.0212 (6)	0.0166 (5)	0.0005 (5)	0.0080 (4)	−0.0013 (4)
C2	0.0211 (6)	0.0265 (7)	0.0200 (5)	0.0019 (5)	0.0109 (5)	−0.0001 (5)
C3	0.0179 (5)	0.0281 (7)	0.0202 (5)	−0.0016 (5)	0.0060 (4)	0.0021 (5)
C4	0.0220 (6)	0.0243 (6)	0.0174 (5)	−0.0009 (5)	0.0059 (4)	−0.0019 (4)
C5	0.0217 (6)	0.0237 (6)	0.0159 (5)	0.0031 (5)	0.0082 (4)	−0.0002 (4)
C6	0.0174 (5)	0.0209 (6)	0.0143 (5)	0.0013 (4)	0.0067 (4)	0.0027 (4)
C7	0.0203 (5)	0.0224 (6)	0.0160 (5)	0.0042 (5)	0.0097 (4)	0.0019 (4)
C8	0.0178 (5)	0.0244 (6)	0.0177 (5)	0.0016 (5)	0.0099 (4)	0.0023 (4)
C9	0.0181 (5)	0.0225 (6)	0.0177 (5)	0.0016 (5)	0.0078 (4)	0.0015 (4)
C10	0.0163 (5)	0.0283 (7)	0.0175 (5)	0.0002 (5)	0.0070 (4)	−0.0029 (4)
C11	0.0191 (6)	0.0394 (8)	0.0193 (6)	−0.0026 (5)	0.0087 (5)	0.0010 (5)
C12	0.0207 (6)	0.0588 (11)	0.0263 (6)	−0.0031 (7)	0.0142 (5)	−0.0045 (6)
C13	0.0218 (6)	0.0590 (11)	0.0344 (7)	0.0097 (7)	0.0119 (6)	−0.0071 (7)
C14	0.0295 (7)	0.0401 (9)	0.0288 (7)	0.0129 (6)	0.0090 (6)	0.0007 (6)
C15	0.0246 (6)	0.0314 (7)	0.0221 (6)	0.0039 (6)	0.0110 (5)	−0.0006 (5)
C16	0.0211 (6)	0.0321 (7)	0.0207 (6)	−0.0027 (5)	0.0071 (5)	−0.0019 (5)
C17	0.0301 (7)	0.0347 (8)	0.0194 (6)	−0.0042 (6)	0.0078 (5)	−0.0055 (5)

Geometric parameters (Å, º) top

F1—C3	1.3644 (14)	C8—C9	1.3708 (16)
O1—C8	1.3763 (15)	C9—C16	1.4928 (17)
O1—C10	1.3941 (15)	C10—C15	1.3809 (18)
O2—C7	1.2544 (14)	C10—C11	1.3837 (18)
N1—C7	1.3851 (15)	C11—C12	1.3907 (19)
N1—N2	1.3862 (13)	C11—H11A	0.9300
N1—C6	1.4202 (16)	C12—C13	1.382 (2)
N2—C9	1.3529 (16)	C12—H12A	0.9300
N2—H1N2	0.899 (18)	C13—C14	1.388 (2)
C1—C2	1.3866 (17)	C13—H13A	0.9300
C1—C6	1.3915 (17)	C14—C15	1.3922 (19)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.3761 (18)	C15—H15A	0.9300
C2—H2A	0.9300	C16—C17	1.5255 (19)
C3—C4	1.3806 (18)	C16—H16A	0.9700
C4—C5	1.3848 (17)	C16—H16B	0.9700
C4—H4A	0.9300	C17—H17A	0.9600
C5—C6	1.3934 (17)	C17—H17B	0.9600
C5—H5A	0.9300	C17—H17C	0.9600
C7—C8	1.4206 (17)

C8—O1—C10	118.93 (10)	N2—C9—C16	122.23 (11)
C7—N1—N2	109.59 (10)	C8—C9—C16	129.65 (12)
C7—N1—C6	127.91 (9)	C15—C10—C11	121.70 (12)
N2—N1—C6	119.98 (9)	C15—C10—O1	123.51 (11)
C9—N2—N1	108.32 (9)	C11—C10—O1	114.77 (11)
C9—N2—H1N2	124.6 (11)	C10—C11—C12	118.95 (13)
N1—N2—H1N2	118.8 (11)	C10—C11—H11A	120.5
C2—C1—C6	119.70 (11)	C12—C11—H11A	120.5
C2—C1—H1A	120.1	C13—C12—C11	120.48 (14)
C6—C1—H1A	120.1	C13—C12—H12A	119.8
C3—C2—C1	118.28 (12)	C11—C12—H12A	119.8
C3—C2—H2A	120.9	C12—C13—C14	119.58 (14)
C1—C2—H2A	120.9	C12—C13—H13A	120.2
F1—C3—C2	118.39 (12)	C14—C13—H13A	120.2
F1—C3—C4	118.40 (11)	C13—C14—C15	120.79 (14)
C2—C3—C4	123.20 (12)	C13—C14—H14A	119.6
C3—C4—C5	118.38 (12)	C15—C14—H14A	119.6
C3—C4—H4A	120.8	C10—C15—C14	118.50 (13)
C5—C4—H4A	120.8	C10—C15—H15A	120.8
C4—C5—C6	119.55 (11)	C14—C15—H15A	120.8
C4—C5—H5A	120.2	C9—C16—C17	113.48 (11)
C6—C5—H5A	120.2	C9—C16—H16A	108.9
C1—C6—C5	120.86 (11)	C17—C16—H16A	108.9
C1—C6—N1	119.90 (11)	C9—C16—H16B	108.9
C5—C6—N1	119.23 (11)	C17—C16—H16B	108.9
O2—C7—N1	123.71 (11)	H16A—C16—H16B	107.7
O2—C7—C8	131.88 (11)	C16—C17—H17A	109.5
N1—C7—C8	104.34 (10)	C16—C17—H17B	109.5
C9—C8—O1	127.09 (11)	H17A—C17—H17B	109.5
C9—C8—C7	109.42 (11)	C16—C17—H17C	109.5
O1—C8—C7	122.36 (10)	H17A—C17—H17C	109.5
N2—C9—C8	108.11 (10)	H17B—C17—H17C	109.5

C7—N1—N2—C9	4.94 (14)	O2—C7—C8—C9	−174.87 (14)
C6—N1—N2—C9	168.32 (11)	N1—C7—C8—C9	2.11 (14)
C6—C1—C2—C3	1.35 (18)	O2—C7—C8—O1	−6.2 (2)
C1—C2—C3—F1	179.00 (11)	N1—C7—C8—O1	170.74 (11)
C1—C2—C3—C4	−0.4 (2)	N1—N2—C9—C8	−3.48 (14)
F1—C3—C4—C5	179.60 (11)	N1—N2—C9—C16	177.94 (12)
C2—C3—C4—C5	−1.0 (2)	O1—C8—C9—N2	−167.13 (12)
C3—C4—C5—C6	1.43 (18)	C7—C8—C9—N2	0.83 (15)
C2—C1—C6—C5	−0.93 (18)	O1—C8—C9—C16	11.3 (2)
C2—C1—C6—N1	177.66 (11)	C7—C8—C9—C16	179.27 (13)
C4—C5—C6—C1	−0.49 (18)	C8—O1—C10—C15	13.96 (18)
C4—C5—C6—N1	−179.09 (11)	C8—O1—C10—C11	−167.62 (11)
C7—N1—C6—C1	137.38 (13)	C15—C10—C11—C12	−0.4 (2)
N2—N1—C6—C1	−22.65 (17)	O1—C10—C11—C12	−178.89 (12)
C7—N1—C6—C5	−44.01 (18)	C10—C11—C12—C13	0.4 (2)
N2—N1—C6—C5	155.96 (11)	C11—C12—C13—C14	0.1 (2)
N2—N1—C7—O2	173.06 (12)	C12—C13—C14—C15	−0.6 (2)
C6—N1—C7—O2	11.4 (2)	C11—C10—C15—C14	−0.1 (2)
N2—N1—C7—C8	−4.24 (13)	O1—C10—C15—C14	178.25 (12)
C6—N1—C7—C8	−165.94 (12)	C13—C14—C15—C10	0.6 (2)
C10—O1—C8—C9	−87.43 (16)	N2—C9—C16—C17	30.45 (18)
C10—O1—C8—C7	106.04 (13)	C8—C9—C16—C17	−147.80 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2ⁱ	0.899 (18)	1.803 (18)	2.6865 (14)	167.1 (16)
C11—H11A···F1ⁱⁱ	0.93	2.52	3.3441 (16)	147

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅FN₂O₂
M_r	298.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	15.332 (2), 8.6833 (14), 11.6066 (19)
β (°)	109.916 (3)
V (Å³)	1452.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.55 × 0.14 × 0.08

Data collection
Diffractometer	Bruker APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.947, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	12927, 4247, 3207
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.119, 1.05
No. of reflections	4247
No. of parameters	204
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.24

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
N2—H1N2···O2ⁱ	0.899 (18)	1.803 (18)	2.6865 (14)	167.1 (16)
C11—H11A···F1ⁱⁱ	0.93	2.52	3.3441 (16)	147

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSH also thanks USM for the award of a research fellowship. VV is grateful to the DST–India for funding through the Young Scientist Scheme (Fast Track Proposal).

References

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