organic compounds
1-[5-(4-Bromophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]butan-1-one
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
In the title compound, C19H18BrFN2O, the benzene rings form dihedral angles of 5.38 (7) and 85.48 (7)° with the mean plane of the 4,5-dihydro-1H-pyrazole ring (r.m.s. deviation = 0.0849 Å), which approximates to an with the –CH2– group as the flap. The dihedral angle between the benzene rings is 82.86 (7)°. In the crystal, C—H⋯F and C—H⋯O hydrogen bonds link the molecules to form inversion dimers and together these generate chains along [011]. The crystal packing also features C—H⋯π interactions.
Related literature
For background to pyrazoline derivatives, see: Fun et al. (2010); Samshuddin et al. (2011). For related structures, see: Fun, Quah et al. (2012); Fun, Loh et al. (2012). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell 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
10.1107/S1600536812034368/hb6918sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812034368/hb6918Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812034368/hb6918Isup3.cml
A mixture of (2E)-3-(4-bromophenyl)-1-(4-fluorophenyl)prop-2-en-1-one (3.05 g, 0.01 mol) and hydrazine hydrate (0.48 ml, 0.01 mol) in 30 ml butyric 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. Colourless plates were grown from acetone solution by slow evaporation method. M. p.: 383–385 K.
All the H atoms were located geometrically and were refined using a riding model with Uiso(H) = 1.2 or 1.5 Ueq(C) [C–H = 0.95 to 0.99 Å]. A rotating group model was applied to the methyl group. In the final
eighteen outliners were omitted, 3 - 3 7, 0 - 3 10, 4 0 3, 2 - 4 9, 2 0 2, 4 - 1 4, 1 0 0, -2 4 6, 2 5 1, -1 2 4, 1 0 5, -2 2 6, -2 5 4, 0 6 3, -1 - 1 8, 1 - 3 9, 15 2 and 1 2 1.Data collection: APEX2 (Bruker, 2009); cell
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).Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids. | |
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. |
C19H18BrFN2O | Z = 2 |
Mr = 389.26 | F(000) = 396 |
Triclinic, P1 | Dx = 1.543 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.7502 (3) Å | Cell parameters from 9994 reflections |
b = 10.1253 (5) Å | θ = 3.1–33.0° |
c = 13.7792 (8) Å | µ = 2.47 mm−1 |
α = 105.354 (1)° | T = 100 K |
β = 98.976 (1)° | Plate, colourless |
γ = 107.369 (1)° | 0.28 × 0.23 × 0.08 mm |
V = 838.01 (7) Å3 |
Bruker SMART APEXII DUO CCD diffractometer | 4816 independent reflections |
Radiation source: fine-focus sealed tube | 4458 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ϕ and ω scans | θmax = 30.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −9→9 |
Tmin = 0.546, Tmax = 0.823 | k = −14→14 |
17838 measured reflections | l = −19→19 |
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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.066 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0342P)2 + 0.3618P] where P = (Fo2 + 2Fc2)/3 |
4816 reflections | (Δ/σ)max = 0.001 |
218 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.63 e Å−3 |
C19H18BrFN2O | γ = 107.369 (1)° |
Mr = 389.26 | V = 838.01 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.7502 (3) Å | Mo Kα radiation |
b = 10.1253 (5) Å | µ = 2.47 mm−1 |
c = 13.7792 (8) Å | T = 100 K |
α = 105.354 (1)° | 0.28 × 0.23 × 0.08 mm |
β = 98.976 (1)° |
Bruker SMART APEXII DUO CCD diffractometer | 4816 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 4458 reflections with I > 2σ(I) |
Tmin = 0.546, Tmax = 0.823 | Rint = 0.023 |
17838 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.066 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.49 e Å−3 |
4816 reflections | Δρmin = −0.63 e Å−3 |
218 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.29346 (2) | 1.105034 (15) | 0.629792 (11) | 0.02435 (5) | |
F1 | 1.22640 (16) | 0.30984 (10) | 0.49188 (7) | 0.02653 (19) | |
O1 | 0.44837 (15) | 0.73712 (10) | 0.95847 (7) | 0.01715 (18) | |
N1 | 0.69619 (17) | 0.56573 (11) | 0.78382 (8) | 0.01292 (18) | |
N2 | 0.65164 (17) | 0.67234 (11) | 0.85431 (8) | 0.01310 (19) | |
C1 | 0.8653 (2) | 0.39253 (14) | 0.64641 (10) | 0.0171 (2) | |
H1A | 0.7351 | 0.3438 | 0.6608 | 0.020* | |
C2 | 0.9522 (2) | 0.31297 (15) | 0.57824 (11) | 0.0201 (2) | |
H2A | 0.8834 | 0.2100 | 0.5457 | 0.024* | |
C3 | 1.1414 (2) | 0.38745 (16) | 0.55897 (10) | 0.0184 (2) | |
C4 | 1.2486 (2) | 0.53618 (15) | 0.60412 (10) | 0.0175 (2) | |
H4A | 1.3788 | 0.5836 | 0.5892 | 0.021* | |
C5 | 1.1603 (2) | 0.61528 (14) | 0.67260 (10) | 0.0150 (2) | |
H5A | 1.2310 | 0.7182 | 0.7049 | 0.018* | |
C6 | 0.96862 (19) | 0.54438 (13) | 0.69403 (9) | 0.0133 (2) | |
C7 | 0.87764 (19) | 0.62814 (13) | 0.76656 (9) | 0.0127 (2) | |
C8 | 0.98525 (19) | 0.78883 (13) | 0.83134 (10) | 0.0149 (2) | |
H8A | 1.0376 | 0.8493 | 0.7883 | 0.018* | |
H8B | 1.1065 | 0.8046 | 0.8891 | 0.018* | |
C9 | 0.80040 (19) | 0.82300 (13) | 0.87232 (9) | 0.0131 (2) | |
H9A | 0.8511 | 0.8801 | 0.9484 | 0.016* | |
C10 | 0.68978 (19) | 0.89988 (13) | 0.81387 (9) | 0.0129 (2) | |
C11 | 0.6768 (2) | 0.87756 (14) | 0.70818 (10) | 0.0165 (2) | |
H11A | 0.7482 | 0.8192 | 0.6735 | 0.020* | |
C12 | 0.5613 (2) | 0.93907 (14) | 0.65294 (10) | 0.0183 (2) | |
H12A | 0.5527 | 0.9229 | 0.5810 | 0.022* | |
C13 | 0.4586 (2) | 1.02469 (14) | 0.70504 (10) | 0.0167 (2) | |
C14 | 0.4748 (2) | 1.05360 (13) | 0.81074 (10) | 0.0158 (2) | |
H14A | 0.4084 | 1.1155 | 0.8458 | 0.019* | |
C15 | 0.59010 (19) | 0.99012 (13) | 0.86442 (9) | 0.0143 (2) | |
H15A | 0.6012 | 1.0085 | 0.9367 | 0.017* | |
C16 | 0.48284 (19) | 0.63837 (13) | 0.89729 (9) | 0.0128 (2) | |
C17 | 0.34922 (19) | 0.47749 (13) | 0.86741 (9) | 0.0137 (2) | |
H17A | 0.4423 | 0.4249 | 0.8877 | 0.016* | |
H17B | 0.2912 | 0.4363 | 0.7909 | 0.016* | |
C18 | 0.1640 (2) | 0.45162 (14) | 0.91894 (10) | 0.0157 (2) | |
H18A | 0.0674 | 0.5007 | 0.8965 | 0.019* | |
H18B | 0.2213 | 0.4959 | 0.9954 | 0.019* | |
C19 | 0.0363 (2) | 0.28890 (16) | 0.89136 (11) | 0.0226 (3) | |
H19A | −0.0778 | 0.2765 | 0.9279 | 0.034* | |
H19B | 0.1321 | 0.2396 | 0.9123 | 0.034* | |
H19C | −0.0274 | 0.2459 | 0.8161 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.02830 (8) | 0.02231 (8) | 0.02494 (8) | 0.01276 (6) | 0.00379 (5) | 0.00926 (5) |
F1 | 0.0359 (5) | 0.0316 (5) | 0.0200 (4) | 0.0222 (4) | 0.0148 (4) | 0.0051 (3) |
O1 | 0.0176 (4) | 0.0163 (4) | 0.0177 (4) | 0.0058 (3) | 0.0095 (3) | 0.0033 (3) |
N1 | 0.0128 (4) | 0.0133 (4) | 0.0136 (4) | 0.0056 (4) | 0.0056 (4) | 0.0037 (4) |
N2 | 0.0127 (4) | 0.0109 (4) | 0.0156 (5) | 0.0035 (4) | 0.0068 (4) | 0.0030 (4) |
C1 | 0.0156 (5) | 0.0162 (5) | 0.0185 (6) | 0.0053 (4) | 0.0053 (5) | 0.0042 (5) |
C2 | 0.0235 (6) | 0.0180 (6) | 0.0174 (6) | 0.0097 (5) | 0.0041 (5) | 0.0018 (5) |
C3 | 0.0242 (6) | 0.0247 (6) | 0.0122 (5) | 0.0163 (5) | 0.0071 (5) | 0.0054 (5) |
C4 | 0.0169 (6) | 0.0244 (6) | 0.0167 (5) | 0.0108 (5) | 0.0085 (5) | 0.0092 (5) |
C5 | 0.0142 (5) | 0.0174 (5) | 0.0153 (5) | 0.0070 (4) | 0.0058 (4) | 0.0058 (4) |
C6 | 0.0128 (5) | 0.0162 (5) | 0.0123 (5) | 0.0069 (4) | 0.0041 (4) | 0.0047 (4) |
C7 | 0.0110 (5) | 0.0134 (5) | 0.0137 (5) | 0.0047 (4) | 0.0036 (4) | 0.0040 (4) |
C8 | 0.0110 (5) | 0.0142 (5) | 0.0187 (5) | 0.0032 (4) | 0.0066 (4) | 0.0037 (4) |
C9 | 0.0117 (5) | 0.0120 (5) | 0.0147 (5) | 0.0026 (4) | 0.0059 (4) | 0.0032 (4) |
C10 | 0.0126 (5) | 0.0115 (5) | 0.0134 (5) | 0.0027 (4) | 0.0057 (4) | 0.0027 (4) |
C11 | 0.0190 (6) | 0.0170 (5) | 0.0154 (5) | 0.0077 (5) | 0.0096 (5) | 0.0041 (4) |
C12 | 0.0224 (6) | 0.0186 (6) | 0.0151 (5) | 0.0072 (5) | 0.0083 (5) | 0.0054 (5) |
C13 | 0.0168 (5) | 0.0142 (5) | 0.0194 (6) | 0.0050 (4) | 0.0054 (5) | 0.0063 (4) |
C14 | 0.0151 (5) | 0.0131 (5) | 0.0193 (6) | 0.0046 (4) | 0.0078 (4) | 0.0036 (4) |
C15 | 0.0145 (5) | 0.0132 (5) | 0.0142 (5) | 0.0034 (4) | 0.0072 (4) | 0.0026 (4) |
C16 | 0.0113 (5) | 0.0154 (5) | 0.0124 (5) | 0.0046 (4) | 0.0041 (4) | 0.0052 (4) |
C17 | 0.0123 (5) | 0.0140 (5) | 0.0146 (5) | 0.0035 (4) | 0.0048 (4) | 0.0048 (4) |
C18 | 0.0127 (5) | 0.0191 (5) | 0.0165 (5) | 0.0039 (4) | 0.0063 (4) | 0.0080 (4) |
C19 | 0.0180 (6) | 0.0216 (6) | 0.0240 (7) | −0.0006 (5) | 0.0067 (5) | 0.0087 (5) |
Br1—C13 | 1.8991 (13) | C9—C10 | 1.5177 (17) |
F1—C3 | 1.3606 (14) | C9—H9A | 1.0000 |
O1—C16 | 1.2322 (15) | C10—C15 | 1.3960 (16) |
N1—C7 | 1.2901 (16) | C10—C11 | 1.3978 (17) |
N1—N2 | 1.3888 (13) | C11—C12 | 1.3894 (19) |
N2—C16 | 1.3608 (15) | C11—H11A | 0.9500 |
N2—C9 | 1.4846 (15) | C12—C13 | 1.3902 (17) |
C1—C2 | 1.3891 (17) | C12—H12A | 0.9500 |
C1—C6 | 1.4013 (17) | C13—C14 | 1.3872 (18) |
C1—H1A | 0.9500 | C14—C15 | 1.3918 (18) |
C2—C3 | 1.381 (2) | C14—H14A | 0.9500 |
C2—H2A | 0.9500 | C15—H15A | 0.9500 |
C3—C4 | 1.375 (2) | C16—C17 | 1.5127 (17) |
C4—C5 | 1.3957 (16) | C17—C18 | 1.5219 (16) |
C4—H4A | 0.9500 | C17—H17A | 0.9900 |
C5—C6 | 1.3975 (17) | C17—H17B | 0.9900 |
C5—H5A | 0.9500 | C18—C19 | 1.5232 (19) |
C6—C7 | 1.4660 (16) | C18—H18A | 0.9900 |
C7—C8 | 1.5148 (17) | C18—H18B | 0.9900 |
C8—C9 | 1.5394 (16) | C19—H19A | 0.9800 |
C8—H8A | 0.9900 | C19—H19B | 0.9800 |
C8—H8B | 0.9900 | C19—H19C | 0.9800 |
C7—N1—N2 | 107.76 (10) | C15—C10—C9 | 120.04 (11) |
C16—N2—N1 | 122.03 (10) | C11—C10—C9 | 121.35 (10) |
C16—N2—C9 | 125.22 (10) | C12—C11—C10 | 121.24 (11) |
N1—N2—C9 | 112.69 (9) | C12—C11—H11A | 119.4 |
C2—C1—C6 | 120.32 (12) | C10—C11—H11A | 119.4 |
C2—C1—H1A | 119.8 | C11—C12—C13 | 118.64 (12) |
C6—C1—H1A | 119.8 | C11—C12—H12A | 120.7 |
C3—C2—C1 | 118.28 (12) | C13—C12—H12A | 120.7 |
C3—C2—H2A | 120.9 | C14—C13—C12 | 121.63 (12) |
C1—C2—H2A | 120.9 | C14—C13—Br1 | 119.20 (9) |
F1—C3—C4 | 118.22 (12) | C12—C13—Br1 | 119.17 (10) |
F1—C3—C2 | 118.38 (12) | C13—C14—C15 | 118.73 (11) |
C4—C3—C2 | 123.40 (12) | C13—C14—H14A | 120.6 |
C3—C4—C5 | 117.96 (12) | C15—C14—H14A | 120.6 |
C3—C4—H4A | 121.0 | C14—C15—C10 | 121.14 (11) |
C5—C4—H4A | 121.0 | C14—C15—H15A | 119.4 |
C4—C5—C6 | 120.54 (12) | C10—C15—H15A | 119.4 |
C4—C5—H5A | 119.7 | O1—C16—N2 | 119.59 (11) |
C6—C5—H5A | 119.7 | O1—C16—C17 | 123.68 (11) |
C5—C6—C1 | 119.50 (11) | N2—C16—C17 | 116.72 (10) |
C5—C6—C7 | 120.20 (11) | C16—C17—C18 | 112.50 (10) |
C1—C6—C7 | 120.30 (11) | C16—C17—H17A | 109.1 |
N1—C7—C6 | 121.06 (11) | C18—C17—H17A | 109.1 |
N1—C7—C8 | 113.62 (10) | C16—C17—H17B | 109.1 |
C6—C7—C8 | 125.25 (10) | C18—C17—H17B | 109.1 |
C7—C8—C9 | 101.79 (9) | H17A—C17—H17B | 107.8 |
C7—C8—H8A | 111.4 | C17—C18—C19 | 111.82 (11) |
C9—C8—H8A | 111.4 | C17—C18—H18A | 109.3 |
C7—C8—H8B | 111.4 | C19—C18—H18A | 109.3 |
C9—C8—H8B | 111.4 | C17—C18—H18B | 109.3 |
H8A—C8—H8B | 109.3 | C19—C18—H18B | 109.3 |
N2—C9—C10 | 110.08 (10) | H18A—C18—H18B | 107.9 |
N2—C9—C8 | 100.37 (9) | C18—C19—H19A | 109.5 |
C10—C9—C8 | 114.80 (10) | C18—C19—H19B | 109.5 |
N2—C9—H9A | 110.4 | H19A—C19—H19B | 109.5 |
C10—C9—H9A | 110.4 | C18—C19—H19C | 109.5 |
C8—C9—H9A | 110.4 | H19A—C19—H19C | 109.5 |
C15—C10—C11 | 118.55 (11) | H19B—C19—H19C | 109.5 |
C7—N1—N2—C16 | −172.51 (11) | C7—C8—C9—N2 | 17.81 (11) |
C7—N1—N2—C9 | 10.01 (13) | C7—C8—C9—C10 | −100.16 (11) |
C6—C1—C2—C3 | −0.1 (2) | N2—C9—C10—C15 | 94.86 (13) |
C1—C2—C3—F1 | −179.72 (12) | C8—C9—C10—C15 | −152.80 (11) |
C1—C2—C3—C4 | 0.3 (2) | N2—C9—C10—C11 | −82.31 (14) |
F1—C3—C4—C5 | 179.79 (11) | C8—C9—C10—C11 | 30.03 (16) |
C2—C3—C4—C5 | −0.2 (2) | C15—C10—C11—C12 | −2.23 (19) |
C3—C4—C5—C6 | −0.02 (19) | C9—C10—C11—C12 | 174.98 (12) |
C4—C5—C6—C1 | 0.20 (19) | C10—C11—C12—C13 | 0.3 (2) |
C4—C5—C6—C7 | 179.61 (11) | C11—C12—C13—C14 | 2.1 (2) |
C2—C1—C6—C5 | −0.13 (19) | C11—C12—C13—Br1 | −178.25 (10) |
C2—C1—C6—C7 | −179.54 (12) | C12—C13—C14—C15 | −2.6 (2) |
N2—N1—C7—C6 | −179.32 (10) | Br1—C13—C14—C15 | 177.84 (9) |
N2—N1—C7—C8 | 3.50 (14) | C13—C14—C15—C10 | 0.53 (19) |
C5—C6—C7—N1 | 176.94 (12) | C11—C10—C15—C14 | 1.81 (18) |
C1—C6—C7—N1 | −3.66 (18) | C9—C10—C15—C14 | −175.44 (11) |
C5—C6—C7—C8 | −6.23 (18) | N1—N2—C16—O1 | −179.08 (11) |
C1—C6—C7—C8 | 173.18 (12) | C9—N2—C16—O1 | −1.92 (18) |
N1—C7—C8—C9 | −14.48 (14) | N1—N2—C16—C17 | 2.02 (16) |
C6—C7—C8—C9 | 168.48 (11) | C9—N2—C16—C17 | 179.18 (11) |
C16—N2—C9—C10 | −74.12 (14) | O1—C16—C17—C18 | 1.59 (17) |
N1—N2—C9—C10 | 103.27 (11) | N2—C16—C17—C18 | −179.55 (10) |
C16—N2—C9—C8 | 164.49 (11) | C16—C17—C18—C19 | −177.81 (11) |
N1—N2—C9—C8 | −18.12 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11A···F1i | 0.95 | 2.37 | 3.1873 (17) | 144 |
C14—H14A···O1ii | 0.95 | 2.57 | 3.1832 (16) | 122 |
C5—H5A···Cg2iii | 0.95 | 2.68 | 3.5453 (15) | 152 |
C17—H17B···Cg1iv | 0.99 | 2.70 | 3.5488 (14) | 144 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+2, −z+2; (iii) x+1, y, z; (iv) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C19H18BrFN2O |
Mr | 389.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 6.7502 (3), 10.1253 (5), 13.7792 (8) |
α, β, γ (°) | 105.354 (1), 98.976 (1), 107.369 (1) |
V (Å3) | 838.01 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.47 |
Crystal size (mm) | 0.28 × 0.23 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART APEXII DUO CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.546, 0.823 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17838, 4816, 4458 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.066, 1.06 |
No. of reflections | 4816 |
No. of parameters | 218 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.49, −0.63 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11A···F1i | 0.95 | 2.37 | 3.1873 (17) | 144 |
C14—H14A···O1ii | 0.95 | 2.57 | 3.1832 (16) | 122 |
C5—H5A···Cg2iii | 0.95 | 2.68 | 3.5453 (15) | 152 |
C17—H17B···Cg1iv | 0.99 | 2.70 | 3.5488 (14) | 144 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+2, −z+2; (iii) x+1, y, z; (iv) x−1, y, z. |
Acknowledgements
HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). WSL also thanks the Malaysian government and USM for the post of Research Officer under the Research University Grant (No. 1001/PFIZIK/811160). BN thanks the UGC for financial assistance through SAP and BSR one time grant for the purchase of chemicals.
References
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o582–o583. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Fun, H.-K., Loh, W.-S., Sapnakumari, M., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o2586. CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Quah, C. K., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o975. CSD CrossRef IUCr Journals Google Scholar
Samshuddin, S., Narayana, B., Baktir, Z., Akkurt, M. & Yathirajan, H. S. (2011). Der Pharma Chem. 3, 487–493. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
In continuation of our work on synthesis of pyrazoline derivatives (Fun et al., 2010; Samshuddin et al., 2011), the title compound is prepared and its crystal structure is reported.
In the title compound, Fig. 1, the benzene rings (C1–C6 & C10–C15) form dihedral angles of 5.38 (7) and 85.48 (7)°, respectively, with the mean plane of 4,5-dihydro-1H-pyrazole ring (N1/N2/C7–C9, r.m.s. deviation = 0.0849 Å). The dihedral angle between the two benzene rings is 82.86 (7) °. Bond lengths and angles are comparable with those in related structures (Fun, Quah et al., 2012; Fun, Loh et al., 2012).
In the crystal packing as shown in Fig. 2, C11—H11A···F1 and C14—H14A···O1 hydrogen bonds (Table 1) link the molecules to form dimers, generating chains along the [011]. The crystal packing is further consolidated by C17—H17B···Cg1 and C5—H5A···Cg2 (Table 1) interactions, where Cg1 and Cg2 are the centroids of C1–C5 and C10–C15 benzene rings, respectively.