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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 3| March 2016| x160415
doi:10.1107/S2414314616004156

2-Chloro-6-fluoro­phenyl 4-chloro­benzoate

Yasser Hussein Issa Mohammed,a S. Naveen,b N. K. Lokanath,c H. R. Manjunath,d Mohammed Al-Ghorbania and Shaukath Ara Khanuma*

aDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysuru 570 005, India, bInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India, cDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India, and dDepartment of Physics, Acharya Institute of Technology, Soldevanahalli, Bengaluru 560 107, India
*Correspondence e-mail: shaukathara@yahoo.co.in

Edited by V. V. Chernyshev, Moscow State University, Russia (Received 21 February 2016; accepted 11 March 2016; online 18 March 2016)

In the title compound, C13H7Cl2FO2, the dihedral angle between the aromatic rings is 49.96 (12)° and the fluorine atom is syn to the C=O group. In the crystal, the molecules are linked into [010] chains by C—H⋯O hydro­gen bonds and weak C—H⋯Cl inter­actions link these chains into sheets parallel to the (101) plane.

CCDC references: 1463777; 1464378

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Phenyl benzoate derivatives are widely used as inter­mediates in the synthesis of bioactive compounds (Prashanth et al., 2014[Prashanth, T., Thurusangu, B. R. P., Avin, V., Lakshmi Ranganatha, V., Prabhakar, B. T. & Khanum, S. A. (2014). Eur. J. Med. Chem. 87, 274-283.]; Khanum et al., 2004[Khanum, S. A., Shashikanth, S. & Deepak, A. V. (2004). Bioorg. Chem. 32, 211-222.]), which exhibit a broad range of biological activities. As part of our studies in this area, we obtained the title compound, namely 2-chloro-6-fluoro­phenyl 4-chloro­benzoate, (I), the structure of which we report here.

The mol­ecular structure of (I) (Fig. 1[link]) closely resembles that of 2,6-di­chloro­phenyl 4-chloro­benzoate (Abdoh et al., 2012[Abdoh, M. M. M., Srinivasa Murthy, V., Manjunath, B. C., Shashikanth, S. & Lokanath, N. K. (2012). Acta Cryst. E68, o3449.]), (II), with similar bond lengths and angles. The dihedral angle between the planes of the aromatic rings is 49.96 (12)° [cf. 82.1 (2)° in (II)]. The ester grouping in (I) is twisted at an angle of 66.3 (3)° out of the 2-chloro-6-fluoro­phenyl plane, while it forms a dihedral angle of 10.5 (4)° with the plane of the 2-chloro-6-fluoro­phenyl ring. In the crystal, C—H⋯O hydrogen bonds (Table 1[link]) link the mol­ecules into chains extending along [010] (Fig. 2[link]) and weak C—H⋯Cl inter­actions (Table 1[link]) further link these chains into sheets parallel to (101).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C13—H13⋯O9i 0.93 2.54 3.142 (3) 123
C2—H2⋯Cl7ii 0.93 2.94 3.581 (3) 127
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+1]; (ii) [-x+1, y-{\script{1\over 2}}, -z].
[Figure 1]
Figure 1
The mol­ecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2]
Figure 2
A portion of the crystal packing, viewed approximately down the a axis, and showing the hydrogen-bonded (dashed lines) chain of mol­ecules running in the [010] direction.

Synthesis and crystallization

2-Chloro-6-fluoro­phenol (0.20 mol) was dissolved in di­chloro­methane (DCM) and tri­ethyl­amine (0.45 mol) was added. The reaction mixture was cooled to 273 K. A solution of chloro­benzoyl chloride (0.21 mol) in DCM was added slowly to the reaction mixture and the resulting solution stirred for 3 h. The completion of the reaction was monitored by thin-layer chromatography (TLC) using a 4:1 n-hexa­ne–ethyl acetate solvent mixture. The reaction mass was diluted with DCM (100 ml) and washed successively with 10% sodium hydroxide solution (3 × 40 ml) and water (3 × 30 ml). The organic layer was dried over sodium sulfate and the solid obtained after evaporation of the solvent was recrystallized from ethanol, giving white crystals in good yield (95%; m.p. 325.1–326.5 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined as riding, with Uiso(H) = 1.2–1.5Ueq(C).

Table 2
Experimental details

Crystal data
Chemical formula C13H7Cl2FO2
Mr 285.09
Crystal system, space group Monoclinic, P21
Temperature (K) 296
a, b, c (Å) 3.8882 (3), 11.2750 (7), 13.5058 (8)
β (°) 95.520 (3)
V (Å3) 589.34 (7)
Z 2
Radiation type Cu Kα
μ (mm−1) 5.01
Crystal size (mm) 0.30 × 0.28 × 0.23
 
Data collection
Diffractometer Bruker X8 Proteum
Absorption correction Multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.278, 0.316
No. of measured, independent and observed [I > 2σ(I)] reflections 4587, 1724, 1702
Rint 0.036
(sin θ/λ)max (Å−1) 0.583
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.080, 1.06
No. of reflections 1724
No. of parameters 163
No. of restraints 1
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.27, −0.21
Absolute structure Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 877 Friedel pairs
Absolute structure parameter 0.051 (17)
Computer programs: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Structural data

CCDC references: 1463777; 1464378

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616004156/cv4003sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616004156/cv4003Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616004156/cv4003Isup3.cml

checkCIF report


Comment top

Phenyl benzoate derivatives are widely used as intermediates in the synthesis of novel bioactive compounds (Prashanth et al., 2014; Khanum et al., 2004), which exhibit a broad range of biological activities. In our systematic search for new phenyl benzoate derivatives, we obtained the title compound, 2-chloro-6-fluorophenyl 4-chlorobenzoate, (I), the structure of which we report here.

The molecular structure of (I) (Fig. 1) closely resembles that of 2,6-dichlorophenyl 4-chlorobenzoate (Abdoh et al., 2012), (II), with similar bond lengths and angles. The dihedral angle between the planes of the two aromatic rings is 49.96 (12)° [cf. 82.1 (2)° in (II)]. The keto group in (I) is twisted at an angle of 66.3 (3)° out of the 2-chloro-6-fluorophenyl plane, while it forms a dihedral angle of 10.5 (4)° with the plane of the chlorophenyl ring. In the crystal, intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains extended in the [010] direction (Fig. 2), and weak C—H···Cl interactions (Table 2) link further these chains into sheets parallel to the (101) plane.

Experimental top

2-Chloro-6-fluorophenol (0.20 mol) was dissolved in dichloromethane (DCM) and triethylamine (0.45 mol) was added. The reaction mixture was cooled to 273 K. A solution of chlorobenzoyl chloride (0.21 mol) in DCM was added slowly to the reaction mixture and the resulting solution stirred for 3 h. The completion of the reaction was monitored by thin-layer chromatography (TLC) using a 4:1 n-hexane–ethyl acetate solvent mixture. The reaction mass was diluted with DCM (100 ml) and washed successively with 10% sodium hydroxide solution (3 × 40 ml) and water (3 × 30 ml). The organic layer was dried over sodium sulfate and the solid obtained after evaporation of the solvent was recrystallized from ethanol, giving white crystals in good yield (95%; m.p. 325.1–326.5 K).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were positioned geometrically (C—H= 0.93–0.96 Å) and refined as riding, with Uiso(H) = 1.2–1.5Ueq(C).

Structure description top

Phenyl benzoate derivatives are widely used as intermediates in the synthesis of novel bioactive compounds (Prashanth et al., 2014; Khanum et al., 2004), which exhibit a broad range of biological activities. In our systematic search for new phenyl benzoate derivatives, we obtained the title compound, namely 2-chloro-6-fluorophenyl 4-chlorobenzoate, (I), the structure of which we report here.

The molecular structure of (I) (Fig. 1) closely resembles that of 2,6-dichlorophenyl 4-chlorobenzoate (Abdoh et al., 2012), (II), with similar bond lengths and angles. The dihedral angle between the planes of the two aromatic rings is 49.96 (12)° [cf. 82.1 (2)° in (II)]. The keto group in (I) is twisted at an angle of 66.3 (3)° out of the 2-chloro-6-fluorophenyl plane, while it forms a dihedral angle of 10.5 (4)° with the plane of the 2-chloro-6-fluorophenyl ring. In the crystal, intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains extending in the [010] direction (Fig. 2) and weak C—H···Cl interactions (Table 2) further link these chains into sheets parallel to the (101) plane.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A portion of the crystal packing, viewed approximately down the a axis, and showing the hydrogen-bonded (dashed lines) chain of molecules running in the [010] direction.
2-Chloro-6-fluorophenyl 4-chlorobenzoate top
Crystal data top
C13H7Cl2FO2F(000) = 288
Mr = 285.09Dx = 1.607 Mg m−3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ybCell parameters from 1724 reflections
a = 3.8882 (3) Åθ = 3.3–64.1°
b = 11.2750 (7) ŵ = 5.01 mm−1
c = 13.5058 (8) ÅT = 296 K
β = 95.520 (3)°Prism, white
V = 589.34 (7) Å30.30 × 0.28 × 0.23 mm
Z = 2
Data collection top
Bruker X8 Proteum
diffractometer		1724 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode1702 reflections with I > 2σ(I)
Helios multilayer optics monochromatorRint = 0.036
Detector resolution: 18.4 pixels mm-1θmax = 64.1°, θmin = 3.3°
φ and ω scansh = −4→3
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		k = −12→12
Tmin = 0.278, Tmax = 0.316l = −15→15
4587 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.080 w = 1/[σ2(Fo2) + (0.052P)2 + 0.0506P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
1724 reflectionsΔρmax = 0.27 e Å−3
163 parametersΔρmin = −0.21 e Å−3
1 restraintAbsolute structure: Flack (1983), 877 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.051 (17)
Crystal data top
C13H7Cl2FO2V = 589.34 (7) Å3
Mr = 285.09Z = 2
Monoclinic, P21Cu Kα radiation
a = 3.8882 (3) ŵ = 5.01 mm−1
b = 11.2750 (7) ÅT = 296 K
c = 13.5058 (8) Å0.30 × 0.28 × 0.23 mm
β = 95.520 (3)°
Data collection top
Bruker X8 Proteum
diffractometer		1724 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		1702 reflections with I > 2σ(I)
Tmin = 0.278, Tmax = 0.316Rint = 0.036
4587 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.080Δρmax = 0.27 e Å−3
S = 1.06Δρmin = −0.21 e Å−3
1724 reflectionsAbsolute structure: Flack (1983), 877 Friedel pairs
163 parametersAbsolute structure parameter: 0.051 (17)
1 restraint
Special details top

Experimental. 1H NMR(400 MHz, DMSO-d6 δ p.p.m.)7.39–8.17 (m, 7H, Ar—H).

IR (KBr) (vmax/cm−1):1750 (ester, C=O).

Mass spectra of the compound showed molecular ion peaks at m/z = 285 [M+], 287 (M+2) and 289 (M+4).

Anal. Calcd. for C13H7O2Cl2F: C, 54.77; H, 2.47; Cl, 24.87; F, 6.66. Found: C, 54.57; H, 2.33; Cl, 24.64; F, 6.42%.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
xyzUiso*/Ueq
Cl70.60980 (16)0.92140 (6)0.06763 (5)0.0271 (2)
Cl17−0.06501 (14)0.25211 (6)0.13366 (4)0.0255 (2)
F180.5317 (4)0.34204 (15)0.47450 (11)0.0248 (5)
O90.0700 (4)0.51053 (19)0.37803 (14)0.0225 (6)
O100.3621 (4)0.39889 (16)0.27475 (13)0.0185 (5)
C10.3494 (6)0.6054 (2)0.2487 (2)0.0161 (7)
C20.4895 (6)0.5885 (2)0.1588 (2)0.0185 (7)
C30.5675 (6)0.6864 (2)0.10226 (19)0.0203 (7)
C40.5093 (6)0.7989 (2)0.1372 (2)0.0192 (7)
C50.3728 (6)0.8170 (2)0.2276 (2)0.0205 (8)
C60.2917 (6)0.7197 (2)0.28295 (19)0.0181 (7)
C80.2427 (6)0.5038 (2)0.30924 (18)0.0159 (7)
C110.2481 (6)0.2947 (2)0.3165 (2)0.0170 (7)
C120.3379 (6)0.2650 (3)0.41579 (19)0.0190 (7)
C130.2396 (7)0.1580 (3)0.4542 (2)0.0222 (8)
C140.0485 (7)0.0793 (3)0.3933 (2)0.0243 (8)
C15−0.0440 (6)0.1067 (3)0.2939 (2)0.0228 (8)
C160.0548 (6)0.2149 (2)0.25638 (19)0.0181 (7)
H20.530800.512200.136500.0220*
H30.657900.676000.041600.0240*
H50.336800.893400.250400.0250*
H60.198400.730400.343200.0220*
H130.301900.139300.520600.0270*
H14−0.019200.007300.418900.0290*
H15−0.171000.053000.252900.0270*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl70.0352 (3)0.0206 (3)0.0248 (4)−0.0058 (3)−0.0003 (2)0.0072 (3)
Cl170.0294 (3)0.0285 (4)0.0180 (3)0.0007 (3)−0.0007 (2)−0.0016 (3)
F180.0282 (8)0.0255 (8)0.0193 (8)−0.0051 (6)−0.0047 (6)−0.0002 (7)
O90.0261 (9)0.0216 (10)0.0206 (10)0.0014 (8)0.0069 (7)0.0008 (9)
O100.0233 (8)0.0129 (9)0.0200 (9)−0.0004 (7)0.0056 (7)0.0014 (8)
C10.0159 (11)0.0147 (13)0.0167 (12)−0.0001 (9)−0.0033 (9)0.0012 (10)
C20.0198 (11)0.0149 (14)0.0202 (13)−0.0004 (10)−0.0004 (10)−0.0013 (12)
C30.0230 (11)0.0247 (15)0.0129 (12)−0.0007 (11)−0.0002 (10)0.0004 (11)
C40.0185 (10)0.0183 (14)0.0196 (14)−0.0032 (10)−0.0035 (9)0.0027 (11)
C50.0211 (12)0.0167 (15)0.0225 (14)0.0003 (10)−0.0037 (10)−0.0038 (11)
C60.0180 (10)0.0189 (14)0.0172 (13)0.0024 (10)0.0005 (9)−0.0005 (11)
C80.0166 (11)0.0165 (13)0.0141 (13)0.0011 (10)−0.0013 (9)0.0011 (11)
C110.0174 (10)0.0140 (12)0.0201 (13)0.0003 (10)0.0043 (10)0.0019 (10)
C120.0181 (10)0.0201 (14)0.0186 (12)−0.0005 (10)0.0006 (9)−0.0004 (11)
C130.0225 (12)0.0237 (14)0.0210 (14)0.0019 (11)0.0048 (10)0.0068 (12)
C140.0255 (12)0.0186 (15)0.0299 (15)0.0018 (11)0.0078 (11)0.0058 (13)
C150.0185 (11)0.0195 (14)0.0304 (16)−0.0026 (11)0.0026 (10)−0.0028 (12)
C160.0178 (11)0.0205 (14)0.0159 (12)0.0028 (10)0.0019 (9)−0.0001 (11)
Geometric parameters (Å, º) top
Cl7—C41.736 (2)C11—C121.394 (4)
Cl17—C161.730 (3)C11—C161.384 (3)
F18—C121.355 (3)C12—C131.382 (5)
O9—C81.200 (3)C13—C141.378 (4)
O10—C81.369 (3)C14—C151.391 (4)
O10—C111.394 (3)C15—C161.389 (4)
C1—C21.391 (4)C2—H20.9300
C1—C61.395 (3)C3—H30.9300
C1—C81.489 (3)C5—H50.9300
C2—C31.392 (3)C6—H60.9300
C3—C41.380 (3)C13—H130.9300
C4—C51.392 (4)C14—H140.9300
C5—C61.381 (3)C15—H150.9300
C8—O10—C11117.34 (18)C12—C13—C14119.4 (3)
C2—C1—C6120.3 (2)C13—C14—C15120.5 (3)
C2—C1—C8121.8 (2)C14—C15—C16119.5 (3)
C6—C1—C8117.8 (2)Cl17—C16—C11119.04 (18)
C1—C2—C3119.6 (2)Cl17—C16—C15120.27 (19)
C2—C3—C4119.3 (2)C11—C16—C15120.7 (2)
Cl7—C4—C3119.6 (2)C1—C2—H2120.00
Cl7—C4—C5118.86 (18)C3—C2—H2120.00
C3—C4—C5121.6 (2)C2—C3—H3120.00
C4—C5—C6119.0 (2)C4—C3—H3120.00
C1—C6—C5120.1 (2)C4—C5—H5121.00
O9—C8—O10123.5 (2)C6—C5—H5120.00
O9—C8—C1125.6 (2)C1—C6—H6120.00
O10—C8—C1110.9 (2)C5—C6—H6120.00
O10—C11—C12122.1 (2)C12—C13—H13120.00
O10—C11—C16119.1 (2)C14—C13—H13120.00
C12—C11—C16118.7 (2)C13—C14—H14120.00
F18—C12—C11118.9 (3)C15—C14—H14120.00
F18—C12—C13119.9 (2)C14—C15—H15120.00
C11—C12—C13121.2 (3)C16—C15—H15120.00
C11—O10—C8—C1−172.5 (2)Cl7—C4—C5—C6179.81 (19)
C8—O10—C11—C12−66.3 (3)C4—C5—C6—C10.6 (4)
C8—O10—C11—C16117.2 (2)O10—C11—C12—F182.5 (4)
C11—O10—C8—O96.2 (3)O10—C11—C12—C13−176.0 (2)
C8—C1—C6—C5−177.4 (2)C16—C11—C12—F18179.0 (2)
C2—C1—C8—O1011.7 (3)C16—C11—C12—C130.4 (4)
C6—C1—C8—O910.5 (4)O10—C11—C16—Cl17−4.6 (3)
C2—C1—C8—O9−166.9 (2)O10—C11—C16—C15175.8 (2)
C6—C1—C2—C3−0.9 (4)C12—C11—C16—Cl17178.78 (19)
C8—C1—C2—C3176.5 (2)C12—C11—C16—C15−0.8 (4)
C2—C1—C6—C50.1 (4)F18—C12—C13—C14−178.7 (2)
C6—C1—C8—O10−170.8 (2)C11—C12—C13—C14−0.2 (4)
C1—C2—C3—C41.0 (4)C12—C13—C14—C150.3 (4)
C2—C3—C4—Cl7179.39 (19)C13—C14—C15—C16−0.7 (4)
C2—C3—C4—C5−0.3 (4)C14—C15—C16—Cl17−178.7 (2)
C3—C4—C5—C6−0.5 (4)C14—C15—C16—C110.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O9i0.932.543.142 (3)123
C2—H2···Cl7ii0.932.943.581 (3)127
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) −x+1, y−1/2, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O9i0.932.543.142 (3)123
C2—H2···Cl7ii0.932.943.581 (3)127
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) −x+1, y−1/2, −z.

Experimental details

Crystal data
Chemical formulaC13H7Cl2FO2
Mr285.09
Crystal system, space groupMonoclinic, P21
Temperature (K)296
a, b, c (Å)3.8882 (3), 11.2750 (7), 13.5058 (8)
β (°) 95.520 (3)
V (Å3)589.34 (7)
Z2
Radiation typeCu Kα
µ (mm−1)5.01
Crystal size (mm)0.30 × 0.28 × 0.23
Data collection
DiffractometerBruker X8 Proteum
Absorption correctionMulti-scan
(SADABS; Bruker, 2013)
Tmin, Tmax0.278, 0.316
No. of measured, independent and
observed [I > 2σ(I)] reflections		4587, 1724, 1702
Rint0.036
(sin θ/λ)max (Å−1)0.583
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.080, 1.06
No. of reflections1724
No. of parameters163
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.27, −0.21
Absolute structureFlack (1983), 877 Friedel pairs
Absolute structure parameter0.051 (17)

Computer programs: APEX2 (Bruker, 2013), SAINT (Bruker, 2013), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).

 

Acknowledgements

The authors are grateful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, India, for providing the single-crystal X-ray diffractometer facility. YHIM thanks the University of Hajah, Yemen, for financial support. SAK gratefully acknowledges the financial support provided by the Vision Group of Science and Technology, Government of Karnataka, under the scheme CISEE, Department of Information Technology, Biotechnology and Science and Technology, Bangalore.

References

First citationAbdoh, M. M. M., Srinivasa Murthy, V., Manjunath, B. C., Shashikanth, S. & Lokanath, N. K. (2012). Acta Cryst. E68, o3449.  CSD CrossRef IUCr Journals Google Scholar
 First citationBruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationKhanum, S. A., Shashikanth, S. & Deepak, A. V. (2004). Bioorg. Chem. 32, 211–222.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationPrashanth, T., Thurusangu, B. R. P., Avin, V., Lakshmi Ranganatha, V., Prabhakar, B. T. & Khanum, S. A. (2014). Eur. J. Med. Chem. 87, 274–283.  CrossRef CAS PubMed Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  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.

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 3| March 2016| x160415
doi:10.1107/S2414314616004156
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