1-[3-(4-Fluoro­phen­yl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone

Fun, H.-K.; Ooi, C.W.; Sapnakumari, M.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812033971

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2634

doi:10.1107/S1600536812033971

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1-[3-(4-Fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone

Hoong-Kun Fun,^a ^*‡ Chin Wei Ooi,^a M. Sapnakumari,^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 27 July 2012; accepted 30 July 2012; online 4 August 2012)

In the title compound, C₁₇H₁₅FN₂O, the pyrazoline ring adopts a flattened envelope conformation. The dihedral angle between the fluoro-substituted benzene ring and the phenyl ring is 69.20 (5)°. In the crystal, a pair of C—H⋯O hydrogen bonds link neighbouring molecules, forming an inversion dimer. The crystal structure is further consolidated by C—H⋯π interactions and by a π–π interaction with a centroid–centroid distance of 3.7379 (6) Å.

Related literature

For related structures, see: Fun et al. (2010 , 2012a ,b ); Samshuddin et al. (2011 ). For bond-length data, see: Allen et al. (1987 ). For ring conformations, see: Cremer & Pople (1975 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₇H₁₅FN₂O
M_r = 282.31
Orthorhombic, P b c a
a = 13.0973 (6) Å
b = 8.6104 (4) Å
c = 24.5948 (12) Å
V = 2773.6 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.34 × 0.33 × 0.09 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.969, T_max = 0.991
25040 measured reflections
4069 independent reflections
3442 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.113
S = 1.03
4069 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the pyrazole N1/N2/C7–C9 ring and the phenyl C10–C15 ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1ⁱ	0.99	2.58	3.3797 (13)	138
C1—H1A⋯Cg2ⁱⁱ	0.95	2.85	3.6856 (11)	148
C13—H13A⋯Cg1ⁱⁱⁱ	0.95	2.73	3.6370 (11)	161
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x+1, -y-{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x, y+1, 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/S1600536812033971/is5177sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812033971/is5177Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812033971/is5177Isup3.cml

checkCIF report

Comment top

In continuation of our work on synthesis of pyrazoline derivatives (Fun et al., 2010; Samshuddin et al., 2011), the title compound is prepared and crystal structure is reported.

In the title compound (Fig. 1), the pyrazoline (N1/N2/C7–C9) ring adopts a flattened envelope conformation [pucker atom at C9 with deviation of 0.065 (1) Å] with puckering parameters Q = 0.1082 (10) Å and ϕ = 79.4 (5)° (Cremer & Pople, 1975). The dihedral angle between fluoro-substituted benzene ring (C1–C6) and the phenyl ring (C10–C15) is 69.20 (5)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable with the related structures (Fun et al., 2012a,b).

In the crystal packing (Fig. 2), pairs of C8—H8A···O1 hydrogen bonds (Table 1) link the neighbouring molecules to form dimers. The crystal is further consolidated by C13—H13A···Cg1 and C1—H1A···Cg2 interactions (Table 1), involving the pyrazoline ring (N1/N2/C7–C9; Cg1) and the phenyl ring (C10–C15; Cg2), respectively. A weak π–π interaction is observed with Cg2···Cg2(1-x, 1-y, 1-z) = 3.7379 (6) Å.

Related literature top

For related structures, see: Fun et al. (2010, 2012a,b); Samshuddin et al. (2011). For bond-length data, see: Allen et al. (1987). For ring conformations, see: Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of (2E)-1-(4-fluorophenyl)-3-phenylprop-2-en-1-one (2.26 g, 0.01 mol) and hydrazine hydrate (0.48 ml, 0.01 mol) in 30 ml acetic acid was refluxed for 6 h. The reaction mixture was cooled and poured into 50 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. The single crystals were grown from toluene by slow evaporation method (m.p. 392–394 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 the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	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.

1-[3-(4-Fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone top

Crystal data top

C₁₇H₁₅FN₂O	F(000) = 1184
M_r = 282.31	D_x = 1.352 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8833 reflections
a = 13.0973 (6) Å	θ = 3.0–30.1°
b = 8.6104 (4) Å	µ = 0.10 mm⁻¹
c = 24.5948 (12) Å	T = 100 K
V = 2773.6 (2) Å³	Plate, colourless
Z = 8	0.34 × 0.33 × 0.09 mm

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	4069 independent reflections
Radiation source: fine-focus sealed tube	3442 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 30.1°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→18
T_min = 0.969, T_max = 0.991	k = −9→12
25040 measured reflections	l = −34→34

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) = 0.113	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0593P)² + 0.9304P] where P = (F_o² + 2F_c²)/3
4069 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₇H₁₅FN₂O	V = 2773.6 (2) Å³
M_r = 282.31	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.0973 (6) Å	µ = 0.10 mm⁻¹
b = 8.6104 (4) Å	T = 100 K
c = 24.5948 (12) Å	0.34 × 0.33 × 0.09 mm

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	4069 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3442 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.991	R_int = 0.029
25040 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.03	Δρ_max = 0.38 e Å⁻³
4069 reflections	Δρ_min = −0.24 e Å⁻³
191 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
F1	0.82344 (6)	−0.34824 (9)	0.79260 (3)	0.03354 (18)
O1	0.34443 (6)	0.10960 (9)	0.53136 (3)	0.02267 (17)
N1	0.49592 (6)	−0.01792 (10)	0.64081 (4)	0.01708 (17)
N2	0.46304 (6)	0.06398 (10)	0.59506 (3)	0.01737 (17)
C1	0.76046 (8)	−0.09765 (12)	0.67970 (4)	0.0202 (2)
H1A	0.7939	−0.0381	0.6525	0.024*
C2	0.81782 (8)	−0.18030 (13)	0.71746 (5)	0.0246 (2)
H2A	0.8903	−0.1776	0.7165	0.029*
C3	0.76748 (9)	−0.26591 (13)	0.75618 (4)	0.0242 (2)
C4	0.66219 (9)	−0.27418 (13)	0.75934 (4)	0.0248 (2)
H4A	0.6297	−0.3347	0.7866	0.030*
C5	0.60547 (8)	−0.19140 (13)	0.72153 (4)	0.0223 (2)
H5A	0.5330	−0.1956	0.7228	0.027*
C6	0.65372 (8)	−0.10171 (11)	0.68153 (4)	0.01726 (19)
C7	0.59451 (7)	−0.01827 (11)	0.64033 (4)	0.01611 (18)
C8	0.64134 (7)	0.06184 (12)	0.59202 (4)	0.01745 (19)
H8A	0.6751	−0.0134	0.5675	0.021*
H8B	0.6916	0.1413	0.6035	0.021*
C9	0.54760 (7)	0.13688 (11)	0.56463 (4)	0.01575 (18)
H9A	0.5444	0.1043	0.5256	0.019*
C10	0.54856 (7)	0.31268 (11)	0.56813 (4)	0.01515 (18)
C11	0.49159 (7)	0.39548 (12)	0.60596 (4)	0.0186 (2)
H11A	0.4487	0.3420	0.6308	0.022*
C12	0.49747 (8)	0.55759 (13)	0.60740 (4)	0.0222 (2)
H12A	0.4590	0.6142	0.6335	0.027*
C13	0.55944 (8)	0.63580 (12)	0.57079 (4)	0.0220 (2)
H13A	0.5622	0.7460	0.5713	0.026*
C14	0.61750 (8)	0.55344 (12)	0.53337 (4)	0.0197 (2)
H14A	0.6605	0.6071	0.5086	0.024*
C15	0.61256 (7)	0.39232 (12)	0.53229 (4)	0.01723 (19)
H15A	0.6530	0.3359	0.5070	0.021*
C16	0.36726 (7)	0.04583 (12)	0.57425 (4)	0.01743 (19)
C17	0.29434 (8)	−0.05575 (13)	0.60548 (5)	0.0233 (2)
H17A	0.2245	−0.0367	0.5928	0.035*
H17B	0.2991	−0.0315	0.6443	0.035*
H17C	0.3120	−0.1651	0.5996	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0370 (4)	0.0359 (4)	0.0277 (4)	0.0095 (3)	−0.0118 (3)	0.0057 (3)
O1	0.0190 (4)	0.0253 (4)	0.0237 (4)	−0.0001 (3)	−0.0042 (3)	0.0026 (3)
N1	0.0155 (4)	0.0176 (4)	0.0182 (4)	0.0005 (3)	−0.0008 (3)	0.0014 (3)
N2	0.0127 (4)	0.0187 (4)	0.0207 (4)	−0.0015 (3)	−0.0006 (3)	0.0044 (3)
C1	0.0177 (5)	0.0205 (5)	0.0225 (5)	0.0007 (4)	−0.0028 (4)	−0.0006 (4)
C2	0.0196 (5)	0.0268 (5)	0.0273 (5)	0.0032 (4)	−0.0067 (4)	−0.0010 (4)
C3	0.0298 (6)	0.0226 (5)	0.0202 (5)	0.0072 (4)	−0.0084 (4)	−0.0021 (4)
C4	0.0293 (6)	0.0262 (5)	0.0190 (5)	0.0050 (4)	0.0012 (4)	0.0022 (4)
C5	0.0196 (5)	0.0262 (5)	0.0210 (5)	0.0035 (4)	0.0018 (4)	0.0021 (4)
C6	0.0165 (4)	0.0177 (4)	0.0176 (4)	0.0024 (3)	−0.0012 (3)	−0.0024 (3)
C7	0.0149 (4)	0.0153 (4)	0.0180 (4)	0.0007 (3)	0.0005 (3)	−0.0019 (3)
C8	0.0126 (4)	0.0180 (4)	0.0218 (5)	0.0006 (3)	0.0009 (3)	0.0015 (3)
C9	0.0122 (4)	0.0166 (4)	0.0184 (4)	−0.0010 (3)	0.0008 (3)	0.0009 (3)
C10	0.0123 (4)	0.0170 (4)	0.0161 (4)	0.0002 (3)	−0.0023 (3)	0.0004 (3)
C11	0.0153 (4)	0.0215 (5)	0.0189 (4)	0.0009 (3)	0.0008 (3)	0.0000 (4)
C12	0.0203 (5)	0.0223 (5)	0.0241 (5)	0.0034 (4)	−0.0008 (4)	−0.0055 (4)
C13	0.0219 (5)	0.0166 (4)	0.0275 (5)	−0.0005 (4)	−0.0054 (4)	−0.0019 (4)
C14	0.0160 (4)	0.0203 (5)	0.0230 (5)	−0.0035 (4)	−0.0028 (4)	0.0029 (4)
C15	0.0144 (4)	0.0196 (5)	0.0177 (4)	−0.0002 (3)	−0.0003 (3)	−0.0002 (3)
C16	0.0137 (4)	0.0168 (4)	0.0218 (4)	0.0000 (3)	−0.0003 (3)	−0.0020 (3)
C17	0.0149 (4)	0.0279 (5)	0.0271 (5)	−0.0053 (4)	0.0001 (4)	0.0016 (4)

Geometric parameters (Å, º) top

F1—C3	1.3572 (12)	C8—H8A	0.9900
O1—C16	1.2261 (13)	C8—H8B	0.9900
N1—C7	1.2914 (13)	C9—C10	1.5162 (13)
N1—N2	1.3959 (11)	C9—H9A	1.0000
N2—C16	1.3639 (12)	C10—C11	1.3896 (13)
N2—C9	1.4767 (12)	C10—C15	1.3963 (13)
C1—C2	1.3903 (14)	C11—C12	1.3984 (15)
C1—C6	1.3991 (14)	C11—H11A	0.9500
C1—H1A	0.9500	C12—C13	1.3866 (15)
C2—C3	1.3729 (16)	C12—H12A	0.9500
C2—H2A	0.9500	C13—C14	1.3886 (15)
C3—C4	1.3831 (16)	C13—H13A	0.9500
C4—C5	1.3875 (15)	C14—C15	1.3891 (14)
C4—H4A	0.9500	C14—H14A	0.9500
C5—C6	1.4012 (14)	C15—H15A	0.9500
C5—H5A	0.9500	C16—C17	1.5058 (14)
C6—C7	1.4644 (13)	C17—H17A	0.9800
C7—C8	1.5045 (14)	C17—H17B	0.9800
C8—C9	1.5422 (13)	C17—H17C	0.9800

C7—N1—N2	107.59 (8)	N2—C9—C8	101.40 (7)
C16—N2—N1	121.90 (8)	C10—C9—C8	112.76 (8)
C16—N2—C9	123.25 (8)	N2—C9—H9A	109.6
N1—N2—C9	113.07 (8)	C10—C9—H9A	109.6
C2—C1—C6	120.37 (10)	C8—C9—H9A	109.6
C2—C1—H1A	119.8	C11—C10—C15	119.55 (9)
C6—C1—H1A	119.8	C11—C10—C9	123.07 (9)
C3—C2—C1	118.60 (10)	C15—C10—C9	117.35 (8)
C3—C2—H2A	120.7	C10—C11—C12	119.96 (9)
C1—C2—H2A	120.7	C10—C11—H11A	120.0
F1—C3—C2	118.61 (10)	C12—C11—H11A	120.0
F1—C3—C4	118.32 (10)	C13—C12—C11	120.04 (10)
C2—C3—C4	123.06 (10)	C13—C12—H12A	120.0
C3—C4—C5	118.02 (10)	C11—C12—H12A	120.0
C3—C4—H4A	121.0	C12—C13—C14	120.19 (10)
C5—C4—H4A	121.0	C12—C13—H13A	119.9
C4—C5—C6	120.81 (10)	C14—C13—H13A	119.9
C4—C5—H5A	119.6	C13—C14—C15	119.82 (10)
C6—C5—H5A	119.6	C13—C14—H14A	120.1
C1—C6—C5	119.14 (9)	C15—C14—H14A	120.1
C1—C6—C7	119.65 (9)	C14—C15—C10	120.42 (9)
C5—C6—C7	121.15 (9)	C14—C15—H15A	119.8
N1—C7—C6	121.63 (9)	C10—C15—H15A	119.8
N1—C7—C8	114.44 (9)	O1—C16—N2	119.73 (9)
C6—C7—C8	123.74 (9)	O1—C16—C17	122.97 (9)
C7—C8—C9	102.27 (8)	N2—C16—C17	117.29 (9)
C7—C8—H8A	111.3	C16—C17—H17A	109.5
C9—C8—H8A	111.3	C16—C17—H17B	109.5
C7—C8—H8B	111.3	H17A—C17—H17B	109.5
C9—C8—H8B	111.3	C16—C17—H17C	109.5
H8A—C8—H8B	109.2	H17A—C17—H17C	109.5
N2—C9—C10	113.69 (8)	H17B—C17—H17C	109.5

C7—N1—N2—C16	159.15 (9)	N1—N2—C9—C10	−110.76 (9)
C7—N1—N2—C9	−6.08 (11)	C16—N2—C9—C8	−154.47 (9)
C6—C1—C2—C3	0.25 (16)	N1—N2—C9—C8	10.53 (10)
C1—C2—C3—F1	179.15 (9)	C7—C8—C9—N2	−10.18 (9)
C1—C2—C3—C4	0.17 (17)	C7—C8—C9—C10	111.76 (9)
F1—C3—C4—C5	−179.15 (10)	N2—C9—C10—C11	14.38 (13)
C2—C3—C4—C5	−0.16 (17)	C8—C9—C10—C11	−100.34 (10)
C3—C4—C5—C6	−0.26 (16)	N2—C9—C10—C15	−167.56 (8)
C2—C1—C6—C5	−0.66 (15)	C8—C9—C10—C15	77.72 (11)
C2—C1—C6—C7	−177.92 (9)	C15—C10—C11—C12	0.96 (14)
C4—C5—C6—C1	0.67 (16)	C9—C10—C11—C12	178.98 (9)
C4—C5—C6—C7	177.89 (10)	C10—C11—C12—C13	0.55 (15)
N2—N1—C7—C6	−176.87 (8)	C11—C12—C13—C14	−1.38 (16)
N2—N1—C7—C8	−1.65 (11)	C12—C13—C14—C15	0.69 (15)
C1—C6—C7—N1	−179.40 (9)	C13—C14—C15—C10	0.84 (15)
C5—C6—C7—N1	3.40 (15)	C11—C10—C15—C14	−1.66 (14)
C1—C6—C7—C8	5.84 (15)	C9—C10—C15—C14	−179.79 (9)
C5—C6—C7—C8	−171.37 (9)	N1—N2—C16—O1	−173.68 (9)
N1—C7—C8—C9	8.00 (11)	C9—N2—C16—O1	−9.96 (15)
C6—C7—C8—C9	−176.89 (9)	N1—N2—C16—C17	5.37 (14)
C16—N2—C9—C10	84.23 (11)	C9—N2—C16—C17	169.09 (9)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the pyrazole N1/N2/C7–C9 ring and the phenyl C10–C15 ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1ⁱ	0.99	2.58	3.3797 (13)	138
C1—H1A···Cg2ⁱⁱ	0.95	2.85	3.6856 (11)	148
C13—H13A···Cg1ⁱⁱⁱ	0.95	2.73	3.6370 (11)	161

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅FN₂O
M_r	282.31
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	13.0973 (6), 8.6104 (4), 24.5948 (12)
V (Å³)	2773.6 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.34 × 0.33 × 0.09

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.969, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	25040, 4069, 3442
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.113, 1.03
No. of reflections	4069
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.24

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the pyrazole N1/N2/C7–C9 ring and the phenyl C10–C15 ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1ⁱ	0.99	2.58	3.3797 (13)	138
C1—H1A···Cg2ⁱⁱ	0.95	2.85	3.6856 (11)	148
C13—H13A···Cg1ⁱⁱⁱ	0.95	2.73	3.6370 (11)	161

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and CWO thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). CWO also thanks the Malaysian Government and USM for the award of the post of Research Officer under Research University Grant No. 1001/PFIZIK/811160. BN thanks the UGC for financial assistance through the SAP and BSR one-time grant for the purchase of chemicals.

References

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