organic compounds
Ethyl 2-(3,5-difluorophenyl)quinoline-4-carboxylate: a second triclinic polymorph
aDepartment of Chemistry, Mangalore University, Mangaluru 574 199, India, bDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India, dDepartment of Material Science, Mangalore University, Mangaluru 574 199, India, and ePURSE Lab, Mangalagangotri, Mangalore University, Mangaluru 574 199, India
*Correspondence e-mail: madanmx@mangaloreuniversity.ac.in
The title compound, C18H13F2NO2, is a polymorph of the structure reported by Sunitha et al. [Acta Cryst. (2015), E71, o341–o342]. Both compounds crystallize in the triclinic P-1. The principal difference between the two polymorphs lies in the orientation of the carboxylate substituents with respect to the planes of the quinoline ring systems. In the crystal, the packing features C—H⋯O hydrogen bonds together with short C—F⋯π and π–π interactions.
CCDC reference: 1477839
Structure description
The title compound (I), Fig. 1, which crystallizes in the triclinic P, is a polymorph of the structure (II) reported by Sunitha et al. (2015), also in P. In both polymorphs, the difluorophenyl rings lie close to the planes of the quinoline ring system with dihedral angles of 10.85 (10)° for (I) and 7.65 (7)° for (II). In contrast however, the carboxylate substituent in (I) projects away from one face of the quinoline ring system, with the angle between the best fit plane through O12/C10–C15 inclined to the quinoline plane by 42.17 (9)°, while for (II) the carboxylate lies close to the quinoline plane, with a corresponding dihedral angle of ca 5.87 (8)°. The torsion angle between the carboxylate substituent and the quinoline ring system C10—C11—O13—C14 is 176.44 (16)°, indicating a + anti-periplanar conformation. This is opposite to the − anti-periplanar conformation found for (II) (Sunitha et al., 2015). Intramolecular C2—H2⋯O12 and C21—H21⋯N7 hydrogen bonds, Table 1, also affect the overall molecular conformation. The structure of a closely related molecule, 2-(4-chlorophenyl)-6-methyl-4-(3-methylphenyl)quinoline was reported by Prabhuswamy et al. (2012).
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In the crystal, molecules are linked through C19—H19⋯O12 hydrogen bonds into chains parallel to the ab diagonal, Table 1 and Fig. 2. A variety of π–π interactions are observed: Cg1⋯Cg1ii = 3.8199 (11), Cg1⋯Cg2ii = 3.6825 (12) and Cg1⋯Cg3iii = 3.8722 (13) Å, Cg1, Cg2 and Cg3 are the centroids of the N7/C1/C6/C8–C10; C1–C6 and C16–C21 rings, respectively; symmetry codes: (ii) −x, 2 − y, 1 − z; (iii) 1 − x, 2 − y, 1 − z). C20—F23⋯Cg1iii [F⋯Cg1 = 3.6366 (17) Å] and C20—F23⋯Cg3iv [F⋯Cg3 = 3.3445 (18) Å; symmetry code: (iv) 1 − x, 1 − y, 1 − z] interactions also occur.
Synthesis and crystallization
Synthesis was performed using a literature method (Sunitha et al., 2015). Recrystallization was carried out using the slow evaporation technique from ethanol solution.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1477839
10.1107/S2414314616007392/sj4012sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616007392/sj4012Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616007392/sj4012Isup3.cml
Synthesis was performed using a literature method (Sunitha et al., 2015). Recrystallization was carried out using the slow evaporation technique from ethanol.
The title compound (I), Fig. 1, which crystallizes in the triclinic 1, is a polymorph of the structure (II) reported by Sunitha et al. (2015), also in P1. In both polymorphs, the difluorophenyl rings lie close to the planes of the quinoline ring system with dihedral angles of 10.85 (10)° for (I) and 7.65 (7)° for (II). In contrast however, the carboxylate substituent in (I) projects away from one face of the quinoline ring system, with the angle between the best fit plane through O12/C10–C15 inclined to the quinoline plane by 42.17 (9)°, while for (II) the carboxylate lies close to the quinoline plane, with a corresponding dihedral angle of ca 5.87°. The torsion angle between the carboxylate substituent and the quinoline ring system C10—C11—O13—C14 is 176.44 (16)°, suggesting a + anti-periplanar conformation. This is opposite to the - anti-periplanar conformation found for (II) (Sunitha et al., 2015). Intramolecular C2—H2···O12 and C21—H21···N7 hydrogen bonds, Table 1, also affect the overall The structure of a closely related molecule, 2-(4-chlorophenyl)-6-methyl-4-(3-methylphenyl)quinoline was reported by Prabhuswamy et al., 2012).
PIn the crystal, molecules are linked through C19—H19···O12 hydrogen bonds into chains parallel to the ab diagonal, Table 1 and Fig. 2. A variety of π–π interactions, [Cg1···Cg1ii = 3.8199 (11), Cg1···Cg2ii = 3.6825 (12) and Cg1···Cg3iii = 3.8722 (13) Å, Cg1, Cg2 and Cg3 are the centroids of the N7/C1/C6/C8–C10; C1–C6 and C16–C21 rings, respectively; symmetry codes: (ii) -x, 2 - y, 1 - z; (iii) 1 - x, 2 - y, 1 - z) also occur along with C20—F23···Cg1iii [F···Cg1 = 3.6366 (17) Å] and C20—F23···Cg3iv [F···Cg3 = 3.3445 (18) Å; symmetry code: ( iv) 1 - x, 1 - y, 1 - z] contacts.
Data collection: CrystalClear SM-Expert (Rigaku, 2011); cell
CrystalClear SM-Expert (Rigaku, 2011); data reduction: CrystalClear SM-Expert (Rigaku, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).Fig. 1. A view of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level and intramolecular hydrogen bonds are shown as dashed lines. | |
Fig. 2. A view along the a axis of the crystal packing of the title compound. Hydrogen bonds are drawn as dashed lines. |
C18H13F2NO2 | Z = 2 |
Mr = 313.29 | F(000) = 324 |
Triclinic, P1 | Dx = 1.418 Mg m−3 |
a = 8.9998 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.0314 (6) Å | Cell parameters from 3269 reflections |
c = 10.2747 (5) Å | θ = 27.5–3.1° |
α = 67.15 (2)° | µ = 0.11 mm−1 |
β = 72.45 (3)° | T = 293 K |
γ = 82.91 (3)° | Block, colourless |
V = 733.76 (18) Å3 | 0.6 × 0.5 × 0.3 mm |
Rigaku Saturn724+ diffractometer | 2198 reflections with I > 2σ(I) |
Detector resolution: 28.5714 pixels mm-1 | Rint = 0.038 |
profile data from ω–scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (NUMABS; Rigaku 1999) | h = −11→11 |
Tmin = 0.936, Tmax = 0.968 | k = −11→8 |
4288 measured reflections | l = −13→8 |
3269 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.172 | w = 1/[σ2(Fo2) + (0.0867P)2 + 0.0798P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3269 reflections | Δρmax = 0.25 e Å−3 |
209 parameters | Δρmin = −0.20 e Å−3 |
C18H13F2NO2 | γ = 82.91 (3)° |
Mr = 313.29 | V = 733.76 (18) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.9998 (8) Å | Mo Kα radiation |
b = 9.0314 (6) Å | µ = 0.11 mm−1 |
c = 10.2747 (5) Å | T = 293 K |
α = 67.15 (2)° | 0.6 × 0.5 × 0.3 mm |
β = 72.45 (3)° |
Rigaku Saturn724+ diffractometer | 3269 independent reflections |
Absorption correction: multi-scan (NUMABS; Rigaku 1999) | 2198 reflections with I > 2σ(I) |
Tmin = 0.936, Tmax = 0.968 | Rint = 0.038 |
4288 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.25 e Å−3 |
3269 reflections | Δρmin = −0.20 e Å−3 |
209 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
F22 | 0.6825 (2) | 0.7904 (2) | 0.07067 (16) | 0.1001 (6) | |
F23 | 0.67056 (16) | 0.53755 (15) | 0.56697 (16) | 0.0718 (4) | |
O12 | −0.01987 (17) | 1.4064 (2) | 0.24797 (16) | 0.0649 (5) | |
O13 | 0.23514 (16) | 1.42864 (17) | 0.13543 (14) | 0.0531 (4) | |
N7 | 0.24653 (18) | 0.94165 (18) | 0.57154 (16) | 0.0421 (4) | |
C1 | 0.0774 (2) | 1.1781 (2) | 0.51318 (19) | 0.0376 (4) | |
C2 | −0.0454 (2) | 1.2713 (2) | 0.5691 (2) | 0.0480 (5) | |
H2 | −0.0801 | 1.3639 | 0.5047 | 0.058* | |
C3 | −0.1123 (3) | 1.2258 (3) | 0.7167 (2) | 0.0539 (5) | |
H3 | −0.1929 | 1.2874 | 0.7519 | 0.065* | |
C4 | −0.0618 (3) | 1.0881 (3) | 0.8155 (2) | 0.0555 (5) | |
H4 | −0.1086 | 1.0588 | 0.9159 | 0.067* | |
C5 | 0.0558 (2) | 0.9962 (2) | 0.7659 (2) | 0.0503 (5) | |
H5 | 0.0882 | 0.9044 | 0.8329 | 0.060* | |
C6 | 0.1290 (2) | 1.0385 (2) | 0.61443 (19) | 0.0401 (4) | |
C8 | 0.3163 (2) | 0.9798 (2) | 0.43039 (19) | 0.0388 (4) | |
C9 | 0.2746 (2) | 1.1196 (2) | 0.3221 (2) | 0.0405 (4) | |
H9 | 0.3281 | 1.1449 | 0.2234 | 0.049* | |
C10 | 0.1566 (2) | 1.2166 (2) | 0.36229 (19) | 0.0383 (4) | |
C11 | 0.1116 (2) | 1.3604 (2) | 0.2447 (2) | 0.0426 (4) | |
C14 | 0.2048 (3) | 1.5635 (3) | 0.0110 (2) | 0.0608 (6) | |
H14A | 0.1244 | 1.6326 | 0.0450 | 0.073* | |
H14B | 0.1698 | 1.5253 | −0.0509 | 0.073* | |
C15 | 0.3529 (3) | 1.6536 (4) | −0.0731 (3) | 0.0974 (11) | |
H15A | 0.3348 | 1.7481 | −0.1521 | 0.146* | |
H15B | 0.4292 | 1.5865 | −0.1125 | 0.146* | |
H15C | 0.3903 | 1.6842 | −0.0090 | 0.146* | |
C16 | 0.4429 (2) | 0.8708 (2) | 0.3884 (2) | 0.0408 (4) | |
C17 | 0.5062 (3) | 0.8827 (2) | 0.2435 (2) | 0.0534 (5) | |
H17 | 0.4699 | 0.9601 | 0.1686 | 0.064* | |
C18 | 0.6236 (3) | 0.7778 (3) | 0.2130 (3) | 0.0606 (6) | |
C19 | 0.6821 (2) | 0.6602 (3) | 0.3172 (3) | 0.0588 (6) | |
H19 | 0.7611 | 0.5905 | 0.2935 | 0.071* | |
C20 | 0.6169 (2) | 0.6520 (2) | 0.4584 (3) | 0.0509 (5) | |
C21 | 0.4994 (2) | 0.7514 (2) | 0.4975 (2) | 0.0453 (5) | |
H21 | 0.4578 | 0.7395 | 0.5955 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F22 | 0.1142 (14) | 0.0950 (12) | 0.0644 (9) | 0.0349 (10) | 0.0037 (9) | −0.0335 (8) |
F23 | 0.0743 (9) | 0.0543 (8) | 0.0933 (10) | 0.0268 (7) | −0.0468 (8) | −0.0246 (7) |
O12 | 0.0491 (9) | 0.0713 (11) | 0.0610 (10) | 0.0189 (8) | −0.0218 (7) | −0.0113 (8) |
O13 | 0.0508 (8) | 0.0528 (9) | 0.0406 (7) | 0.0100 (6) | −0.0154 (6) | −0.0027 (6) |
N7 | 0.0473 (9) | 0.0345 (8) | 0.0422 (8) | 0.0038 (7) | −0.0157 (7) | −0.0108 (6) |
C1 | 0.0384 (9) | 0.0362 (9) | 0.0413 (9) | 0.0023 (7) | −0.0148 (7) | −0.0157 (7) |
C2 | 0.0486 (11) | 0.0452 (11) | 0.0513 (11) | 0.0086 (9) | −0.0183 (9) | −0.0185 (9) |
C3 | 0.0526 (12) | 0.0622 (13) | 0.0511 (11) | 0.0097 (10) | −0.0134 (9) | −0.0291 (10) |
C4 | 0.0596 (13) | 0.0638 (14) | 0.0414 (11) | 0.0027 (11) | −0.0096 (9) | −0.0220 (10) |
C5 | 0.0609 (13) | 0.0481 (12) | 0.0389 (10) | 0.0031 (10) | −0.0164 (9) | −0.0121 (8) |
C6 | 0.0433 (10) | 0.0377 (9) | 0.0419 (10) | 0.0013 (8) | −0.0162 (8) | −0.0146 (8) |
C8 | 0.0400 (10) | 0.0338 (9) | 0.0426 (10) | 0.0035 (7) | −0.0139 (8) | −0.0135 (7) |
C9 | 0.0433 (10) | 0.0388 (10) | 0.0378 (9) | 0.0040 (8) | −0.0136 (8) | −0.0120 (8) |
C10 | 0.0406 (10) | 0.0347 (9) | 0.0402 (9) | 0.0028 (7) | −0.0160 (7) | −0.0120 (7) |
C11 | 0.0477 (11) | 0.0410 (10) | 0.0410 (10) | 0.0097 (8) | −0.0185 (8) | −0.0156 (8) |
C14 | 0.0688 (15) | 0.0597 (14) | 0.0434 (11) | 0.0182 (11) | −0.0256 (10) | −0.0059 (10) |
C15 | 0.0709 (18) | 0.095 (2) | 0.0630 (16) | 0.0102 (16) | −0.0056 (13) | 0.0247 (15) |
C16 | 0.0382 (9) | 0.0333 (9) | 0.0508 (10) | 0.0025 (7) | −0.0128 (8) | −0.0159 (8) |
C17 | 0.0556 (12) | 0.0439 (11) | 0.0512 (12) | 0.0080 (9) | −0.0117 (9) | −0.0124 (9) |
C18 | 0.0615 (14) | 0.0524 (13) | 0.0585 (13) | 0.0042 (11) | −0.0012 (10) | −0.0235 (10) |
C19 | 0.0447 (12) | 0.0472 (12) | 0.0803 (16) | 0.0114 (9) | −0.0109 (11) | −0.0278 (11) |
C20 | 0.0447 (11) | 0.0358 (10) | 0.0756 (14) | 0.0069 (8) | −0.0284 (10) | −0.0175 (9) |
C21 | 0.0456 (11) | 0.0398 (10) | 0.0535 (11) | 0.0032 (8) | −0.0189 (9) | −0.0176 (9) |
F22—C18 | 1.360 (3) | C8—C16 | 1.487 (2) |
F23—C20 | 1.361 (2) | C9—H9 | 0.9300 |
O12—C11 | 1.200 (2) | C9—C10 | 1.361 (2) |
O13—C11 | 1.325 (2) | C10—C11 | 1.503 (2) |
O13—C14 | 1.453 (2) | C14—H14A | 0.9700 |
N7—C6 | 1.367 (2) | C14—H14B | 0.9700 |
N7—C8 | 1.316 (2) | C14—C15 | 1.487 (4) |
C1—C2 | 1.422 (3) | C15—H15A | 0.9600 |
C1—C6 | 1.420 (2) | C15—H15B | 0.9600 |
C1—C10 | 1.417 (3) | C15—H15C | 0.9600 |
C2—H2 | 0.9300 | C16—C17 | 1.390 (3) |
C2—C3 | 1.362 (3) | C16—C21 | 1.395 (3) |
C3—H3 | 0.9300 | C17—H17 | 0.9300 |
C3—C4 | 1.394 (3) | C17—C18 | 1.377 (3) |
C4—H4 | 0.9300 | C18—C19 | 1.368 (3) |
C4—C5 | 1.362 (3) | C19—H19 | 0.9300 |
C5—H5 | 0.9300 | C19—C20 | 1.367 (3) |
C5—C6 | 1.408 (3) | C20—C21 | 1.370 (3) |
C8—C9 | 1.420 (2) | C21—H21 | 0.9300 |
C11—O13—C14 | 116.37 (15) | O13—C11—C10 | 111.54 (15) |
C8—N7—C6 | 118.80 (15) | O13—C14—H14A | 110.2 |
C6—C1—C2 | 118.52 (17) | O13—C14—H14B | 110.2 |
C10—C1—C2 | 124.76 (16) | O13—C14—C15 | 107.47 (18) |
C10—C1—C6 | 116.69 (16) | H14A—C14—H14B | 108.5 |
C1—C2—H2 | 119.8 | C15—C14—H14A | 110.2 |
C3—C2—C1 | 120.33 (18) | C15—C14—H14B | 110.2 |
C3—C2—H2 | 119.8 | C14—C15—H15A | 109.5 |
C2—C3—H3 | 119.5 | C14—C15—H15B | 109.5 |
C2—C3—C4 | 120.9 (2) | C14—C15—H15C | 109.5 |
C4—C3—H3 | 119.5 | H15A—C15—H15B | 109.5 |
C3—C4—H4 | 119.8 | H15A—C15—H15C | 109.5 |
C5—C4—C3 | 120.36 (19) | H15B—C15—H15C | 109.5 |
C5—C4—H4 | 119.8 | C17—C16—C8 | 122.06 (17) |
C4—C5—H5 | 119.6 | C17—C16—C21 | 118.63 (18) |
C4—C5—C6 | 120.87 (18) | C21—C16—C8 | 119.30 (17) |
C6—C5—H5 | 119.6 | C16—C17—H17 | 120.6 |
N7—C6—C1 | 122.89 (16) | C18—C17—C16 | 118.79 (19) |
N7—C6—C5 | 118.10 (16) | C18—C17—H17 | 120.6 |
C5—C6—C1 | 119.01 (18) | F22—C18—C17 | 117.8 (2) |
N7—C8—C9 | 121.95 (17) | F22—C18—C19 | 118.2 (2) |
N7—C8—C16 | 117.07 (16) | C19—C18—C17 | 124.0 (2) |
C9—C8—C16 | 120.97 (16) | C18—C19—H19 | 122.2 |
C8—C9—H9 | 119.9 | C20—C19—C18 | 115.57 (19) |
C10—C9—C8 | 120.18 (17) | C20—C19—H19 | 122.2 |
C10—C9—H9 | 119.9 | F23—C20—C19 | 118.31 (19) |
C1—C10—C11 | 121.64 (16) | F23—C20—C21 | 117.9 (2) |
C9—C10—C1 | 119.46 (16) | C19—C20—C21 | 123.82 (19) |
C9—C10—C11 | 118.89 (16) | C16—C21—H21 | 120.4 |
O12—C11—O13 | 124.14 (17) | C20—C21—C16 | 119.18 (19) |
O12—C11—C10 | 124.31 (18) | C20—C21—H21 | 120.4 |
F22—C18—C19—C20 | −179.1 (2) | C8—C9—C10—C1 | 0.9 (3) |
F23—C20—C21—C16 | 179.44 (16) | C8—C9—C10—C11 | −177.89 (16) |
N7—C8—C9—C10 | −1.8 (3) | C8—C16—C17—C18 | 179.82 (19) |
N7—C8—C16—C17 | 168.68 (18) | C8—C16—C21—C20 | −179.52 (17) |
N7—C8—C16—C21 | −10.6 (3) | C9—C8—C16—C17 | −12.0 (3) |
C1—C2—C3—C4 | 0.3 (3) | C9—C8—C16—C21 | 168.72 (16) |
C1—C10—C11—O12 | −37.0 (3) | C9—C10—C11—O12 | 141.7 (2) |
C1—C10—C11—O13 | 144.05 (17) | C9—C10—C11—O13 | −37.2 (2) |
C2—C1—C6—N7 | −179.66 (16) | C10—C1—C2—C3 | −178.75 (19) |
C2—C1—C6—C5 | 0.8 (3) | C10—C1—C6—N7 | −1.4 (3) |
C2—C1—C10—C9 | 178.70 (17) | C10—C1—C6—C5 | 179.03 (17) |
C2—C1—C10—C11 | −2.5 (3) | C11—O13—C14—C15 | 162.0 (2) |
C2—C3—C4—C5 | −0.1 (3) | C14—O13—C11—O12 | −2.5 (3) |
C3—C4—C5—C6 | 0.3 (3) | C14—O13—C11—C10 | 176.44 (16) |
C4—C5—C6—N7 | 179.84 (18) | C16—C8—C9—C10 | 178.90 (16) |
C4—C5—C6—C1 | −0.6 (3) | C16—C17—C18—F22 | 179.2 (2) |
C6—N7—C8—C9 | 1.0 (3) | C16—C17—C18—C19 | 0.5 (4) |
C6—N7—C8—C16 | −179.68 (15) | C17—C16—C21—C20 | 1.2 (3) |
C6—C1—C2—C3 | −0.7 (3) | C17—C18—C19—C20 | −0.4 (4) |
C6—C1—C10—C9 | 0.6 (3) | C18—C19—C20—F23 | −179.87 (19) |
C6—C1—C10—C11 | 179.39 (16) | C18—C19—C20—C21 | 0.7 (3) |
C8—N7—C6—C1 | 0.6 (3) | C19—C20—C21—C16 | −1.1 (3) |
C8—N7—C6—C5 | −179.84 (17) | C21—C16—C17—C18 | −0.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O12 | 0.93 | 2.41 | 2.986 (2) | 120 |
C21—H21···N7 | 0.93 | 2.47 | 2.778 (3) | 100 |
C19—H19···O12i | 0.93 | 2.47 | 3.399 (3) | 175 |
Symmetry code: (i) x+1, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O12 | 0.93 | 2.41 | 2.986 (2) | 120 |
C21—H21···N7 | 0.93 | 2.47 | 2.778 (3) | 100 |
C19—H19···O12i | 0.93 | 2.47 | 3.399 (3) | 175 |
Symmetry code: (i) x+1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C18H13F2NO2 |
Mr | 313.29 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.9998 (8), 9.0314 (6), 10.2747 (5) |
α, β, γ (°) | 67.15 (2), 72.45 (3), 82.91 (3) |
V (Å3) | 733.76 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.6 × 0.5 × 0.3 |
Data collection | |
Diffractometer | Rigaku Saturn724+ |
Absorption correction | Multi-scan (NUMABS; Rigaku 1999) |
Tmin, Tmax | 0.936, 0.968 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4288, 3269, 2198 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.172, 1.05 |
No. of reflections | 3269 |
No. of parameters | 209 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.20 |
Computer programs: CrystalClear SM-Expert (Rigaku, 2011), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), Mercury (Macrae et al., 2008), OLEX2 (Dolomanov et al., 2009).
Acknowledgements
The authors thank the Department of Studies in Physics, University of Mysore, Mysore, India and DST–PURSE, Mangalore University, Mangaluru, for providing the single-crystal X-ray diffraction facility. KK thanks IOE for financial support.
References
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