organic compounds
N-[(3-Bromo-1-phenylsulfonyl-1H-indol-2-yl)methyl]-4-fluoroaniline
aDepartment of Chemistry, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India, and bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: shirai2011@gmail.com
In the title compound, C21H16BrFN2O2S, the indole ring system makes dihedral angles of 87.23 (10) and 77.58 (9)° with the fluorobenzene and phenyl rings, respectively. The molecular structure is stabilized by a C—H⋯O and a C—H⋯Br intramolecular hydrogen bond, which generate S(6) and S(8) ring motifs, respectively. In the crystal, molecules are linked by C—H⋯π interactions, forming ribbons propagating along the a-axis direction. Within the ribbons, there are offset π–π interactions present involving inversion-related molecules [intercentroid distance = 3.650 (1) Å].
Keywords: crystal structure; indole; C—H⋯π interactions; offset π–π interactions; hydrogen bonding.
CCDC reference: 1530001
Structure description
Indole is an important heterocyclic system because it is built into proteins in the form of the amino acid tryptophan as well as being the basis of drugs such as indomethacin and providing the skeleton of indole et al., 2010). As part of our investigations of indole derivatives, we have undertaken the synthesis and analysis of the title compound.
the biologically active compounds from plants (SharmaThe molecular structure of the title compound is shown in Fig. 1. The molecular structure is stabilized by a C—H⋯O and a C—H⋯Br intramolecular hydrogen bond, which generate S(6) and S(8) ring motifs, respectively (Fig. 1 and Table 1). The indole ring system (N2/C8–C15) adopts a planar conformation with a maximum deviation of 0.0340 (1) Å for atom C11. Atom F1 deviates by 0.0107 (1) Å from the plane of the benzene ring (C1–C6) to which it is attached. The mean plane of the indole ring system makes dihedral angles of 87.23 (10) and 77.58 (9)° with the fluorobenzene and phenyl (C16–C21) rings, respectively. The fluorobenzene and phenyl rings are inclined to one another by 81.44 (11)°. The indole and fluorobenzene rings are connected through the atoms N1 and C7 with torsion angle C8—C7—N1—C4 = 66.9 (3)°. Atom S1 has a distorted tetrahedral configuration. The widening of angle O1—S1—O2 = 119.87 (10) ° and narrowing of angle N2—S1—C16 = 105.53 (8)° from the ideal tetrahedral value are attributed to the Thorpe–Ingold effect (Bassindale, 1984).
In the crystal, molecules are linked by C—H⋯π interactions, forming ribbons propagating along the a-axis direction (Table 1 and Fig. 2). Within the ribbons there are offset π–π interactions involving inversion-related molecules [Cg3⋯Cg3iii = 3.650 (1) Å; Cg3 is the centroid of the C10-C15 ring; interplanar distance = 3.440 (1) Å; slippage 1.22 Å; symmetry code: (iii) −x + 2, −y + 2, −z + 1].
Synthesis and crystallization
A solution of 1-phenylsulfonyl-2-bromomethyl-3-bromoindole (1.07 g, 2.5 mmol, 1.0 equiv) and 4-fluoroaniline (0.27 g, 2.5 mmol, 1.0 equiv) in dry DMF (10 ml) containing finely powdered K2CO3 (0.69 g, 5.0 mmol, 2.0 equiv) was stirred at room temperature for 12 h. The reaction mixture was then poured onto ice (200 g) and the solid formed was filtered immediately and washed with an excess of water. The crude product was dried over CaCl2 and recrystallized from ethyl acetate–hexane (1: 9) to give a half-white coloured solid in 72% yield. Block-like colourless crystals were obtained by slow evaporation of a solution in CH3OH.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 1530001
https://doi.org/10.1107/S241431461700147X/su4110sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461700147X/su4110Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S241431461700147X/su4110Isup3.cml
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and SHELXL2016 (Sheldrick, 2015).C21H16BrFN2O2S | Z = 2 |
Mr = 459.33 | F(000) = 464 |
Triclinic, P1 | Dx = 1.623 Mg m−3 |
a = 8.1732 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.5828 (7) Å | Cell parameters from 4427 reflections |
c = 12.1781 (8) Å | θ = 2.2–28.3° |
α = 113.699 (1)° | µ = 2.33 mm−1 |
β = 94.617 (1)° | T = 293 K |
γ = 99.203 (1)° | Block, colourless |
V = 939.81 (11) Å3 | 0.24 × 0.19 × 0.12 mm |
Bruker SMART APEXII area-detector diffractometer | 3778 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.018 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 28.3°, θmin = 2.2° |
Tmin = 0.753, Tmax = 0.856 | h = −10→10 |
11107 measured reflections | k = −13→13 |
4427 independent reflections | l = −15→15 |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0594P)2 + 0.1305P] where P = (Fo2 + 2Fc2)/3 |
4427 reflections | (Δ/σ)max = 0.001 |
253 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
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 | ||
C1 | 1.0439 (3) | 0.3846 (2) | 0.3063 (2) | 0.0524 (5) | |
C2 | 0.8963 (3) | 0.4075 (2) | 0.3480 (2) | 0.0510 (5) | |
H2 | 0.870710 | 0.391539 | 0.415005 | 0.061* | |
C3 | 0.7849 (3) | 0.4548 (2) | 0.2890 (2) | 0.0466 (4) | |
H3 | 0.684493 | 0.471193 | 0.317208 | 0.056* | |
C4 | 0.8213 (3) | 0.47778 (19) | 0.18896 (17) | 0.0433 (4) | |
C5 | 0.9754 (3) | 0.4538 (3) | 0.1506 (2) | 0.0599 (6) | |
H5 | 1.003760 | 0.470852 | 0.084643 | 0.072* | |
C6 | 1.0853 (3) | 0.4057 (3) | 0.2082 (2) | 0.0613 (6) | |
H6 | 1.185730 | 0.387984 | 0.180567 | 0.074* | |
C7 | 0.5735 (3) | 0.5820 (2) | 0.17222 (19) | 0.0491 (5) | |
H7A | 0.507416 | 0.521160 | 0.201672 | 0.059* | |
H7B | 0.500965 | 0.587821 | 0.108060 | 0.059* | |
C8 | 0.6282 (2) | 0.7267 (2) | 0.27416 (17) | 0.0395 (4) | |
C9 | 0.6028 (2) | 0.7717 (2) | 0.39091 (18) | 0.0401 (4) | |
C10 | 0.6911 (2) | 0.9145 (2) | 0.46065 (17) | 0.0396 (4) | |
C11 | 0.7743 (2) | 0.9561 (2) | 0.38144 (16) | 0.0378 (4) | |
C12 | 0.8800 (3) | 1.0883 (2) | 0.4218 (2) | 0.0476 (5) | |
H12 | 0.936670 | 1.115759 | 0.369150 | 0.057* | |
C13 | 0.8966 (3) | 1.1766 (2) | 0.5435 (2) | 0.0562 (5) | |
H13 | 0.966282 | 1.265694 | 0.572957 | 0.067* | |
C14 | 0.8138 (3) | 1.1379 (2) | 0.6233 (2) | 0.0559 (5) | |
H14 | 0.827849 | 1.201048 | 0.704601 | 0.067* | |
C15 | 0.7107 (3) | 1.0068 (2) | 0.58341 (18) | 0.0488 (5) | |
H15 | 0.655233 | 0.980097 | 0.636937 | 0.059* | |
C16 | 0.5460 (2) | 0.9385 (2) | 0.13481 (16) | 0.0372 (4) | |
C17 | 0.5621 (3) | 1.0827 (2) | 0.1861 (2) | 0.0470 (4) | |
H17 | 0.667034 | 1.142071 | 0.220819 | 0.056* | |
C18 | 0.4198 (3) | 1.1384 (2) | 0.1854 (2) | 0.0524 (5) | |
H18 | 0.428905 | 1.235653 | 0.220589 | 0.063* | |
C19 | 0.2653 (3) | 1.0502 (2) | 0.1329 (2) | 0.0493 (5) | |
H19 | 0.170302 | 1.088132 | 0.132396 | 0.059* | |
C20 | 0.2503 (3) | 0.9069 (3) | 0.0815 (2) | 0.0528 (5) | |
H20 | 0.145091 | 0.848001 | 0.046733 | 0.063* | |
C21 | 0.3913 (3) | 0.8489 (2) | 0.08082 (19) | 0.0476 (4) | |
H21 | 0.381825 | 0.751566 | 0.044744 | 0.057* | |
N1 | 0.7090 (2) | 0.51720 (19) | 0.12096 (15) | 0.0522 (4) | |
H1 | 0.721138 | 0.502532 | 0.047600 | 0.063* | |
N2 | 0.73770 (19) | 0.83989 (17) | 0.26447 (13) | 0.0383 (3) | |
O1 | 0.87084 (18) | 0.9732 (2) | 0.15578 (15) | 0.0572 (4) | |
O2 | 0.6999 (2) | 0.73241 (18) | 0.03837 (13) | 0.0560 (4) | |
F1 | 1.1535 (2) | 0.33908 (19) | 0.36508 (16) | 0.0767 (4) | |
S1 | 0.72622 (6) | 0.86853 (6) | 0.13829 (4) | 0.04184 (12) | |
BR1 | 0.47945 (3) | 0.66201 (3) | 0.45649 (2) | 0.05848 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0500 (12) | 0.0487 (11) | 0.0578 (12) | 0.0118 (9) | −0.0011 (10) | 0.0229 (10) |
C2 | 0.0572 (12) | 0.0466 (11) | 0.0526 (11) | 0.0107 (9) | 0.0073 (10) | 0.0245 (9) |
C3 | 0.0459 (10) | 0.0389 (10) | 0.0538 (11) | 0.0094 (8) | 0.0074 (9) | 0.0183 (9) |
C4 | 0.0498 (11) | 0.0313 (9) | 0.0393 (9) | 0.0072 (8) | −0.0008 (8) | 0.0073 (7) |
C5 | 0.0660 (14) | 0.0713 (15) | 0.0523 (12) | 0.0263 (12) | 0.0186 (11) | 0.0300 (11) |
C6 | 0.0515 (12) | 0.0690 (15) | 0.0673 (15) | 0.0207 (11) | 0.0156 (11) | 0.0285 (12) |
C7 | 0.0475 (11) | 0.0483 (11) | 0.0452 (10) | 0.0112 (9) | −0.0048 (9) | 0.0152 (9) |
C8 | 0.0366 (9) | 0.0442 (10) | 0.0396 (9) | 0.0127 (7) | 0.0033 (7) | 0.0184 (8) |
C9 | 0.0362 (9) | 0.0464 (10) | 0.0452 (10) | 0.0126 (8) | 0.0098 (7) | 0.0246 (8) |
C10 | 0.0378 (9) | 0.0467 (10) | 0.0391 (9) | 0.0161 (8) | 0.0069 (7) | 0.0203 (8) |
C11 | 0.0354 (8) | 0.0440 (10) | 0.0375 (9) | 0.0138 (7) | 0.0038 (7) | 0.0189 (8) |
C12 | 0.0465 (11) | 0.0475 (11) | 0.0542 (11) | 0.0104 (8) | 0.0033 (9) | 0.0277 (9) |
C13 | 0.0564 (13) | 0.0419 (11) | 0.0628 (13) | 0.0090 (9) | −0.0057 (11) | 0.0178 (10) |
C14 | 0.0652 (14) | 0.0527 (12) | 0.0440 (11) | 0.0217 (11) | 0.0033 (10) | 0.0122 (10) |
C15 | 0.0551 (12) | 0.0562 (12) | 0.0380 (9) | 0.0203 (10) | 0.0105 (9) | 0.0191 (9) |
C16 | 0.0364 (9) | 0.0482 (10) | 0.0335 (8) | 0.0139 (7) | 0.0097 (7) | 0.0212 (8) |
C17 | 0.0415 (10) | 0.0477 (11) | 0.0555 (11) | 0.0071 (8) | 0.0031 (9) | 0.0274 (9) |
C18 | 0.0535 (12) | 0.0469 (11) | 0.0648 (13) | 0.0168 (9) | 0.0096 (10) | 0.0294 (10) |
C19 | 0.0435 (10) | 0.0625 (13) | 0.0545 (12) | 0.0224 (9) | 0.0130 (9) | 0.0322 (10) |
C20 | 0.0374 (10) | 0.0606 (13) | 0.0563 (12) | 0.0095 (9) | 0.0012 (9) | 0.0219 (10) |
C21 | 0.0459 (11) | 0.0453 (11) | 0.0459 (10) | 0.0112 (8) | 0.0022 (8) | 0.0139 (9) |
N1 | 0.0645 (11) | 0.0503 (10) | 0.0374 (8) | 0.0234 (8) | 0.0025 (8) | 0.0109 (7) |
N2 | 0.0389 (8) | 0.0460 (8) | 0.0344 (7) | 0.0131 (6) | 0.0060 (6) | 0.0199 (7) |
O1 | 0.0391 (7) | 0.0892 (11) | 0.0636 (9) | 0.0172 (7) | 0.0186 (7) | 0.0494 (9) |
O2 | 0.0713 (10) | 0.0687 (10) | 0.0383 (7) | 0.0377 (8) | 0.0178 (7) | 0.0227 (7) |
F1 | 0.0660 (9) | 0.0927 (11) | 0.0872 (11) | 0.0341 (8) | 0.0043 (8) | 0.0487 (9) |
S1 | 0.0396 (2) | 0.0592 (3) | 0.0377 (2) | 0.0207 (2) | 0.01327 (18) | 0.0264 (2) |
BR1 | 0.05446 (15) | 0.06742 (17) | 0.06666 (17) | 0.01190 (11) | 0.02033 (11) | 0.03985 (13) |
C1—C6 | 1.360 (4) | C12—C13 | 1.379 (3) |
C1—F1 | 1.363 (3) | C12—H12 | 0.9300 |
C1—C2 | 1.366 (3) | C13—C14 | 1.381 (4) |
C2—C3 | 1.387 (3) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—C15 | 1.375 (3) |
C3—C4 | 1.380 (3) | C14—H14 | 0.9300 |
C3—H3 | 0.9300 | C15—H15 | 0.9300 |
C4—C5 | 1.403 (3) | C16—C17 | 1.376 (3) |
C4—N1 | 1.407 (3) | C16—C21 | 1.383 (3) |
C5—C6 | 1.374 (3) | C16—S1 | 1.7562 (18) |
C5—H5 | 0.9300 | C17—C18 | 1.386 (3) |
C6—H6 | 0.9300 | C17—H17 | 0.9300 |
C7—N1 | 1.449 (3) | C18—C19 | 1.374 (3) |
C7—C8 | 1.500 (3) | C18—H18 | 0.9300 |
C7—H7A | 0.9700 | C19—C20 | 1.368 (3) |
C7—H7B | 0.9700 | C19—H19 | 0.9300 |
C8—C9 | 1.351 (3) | C20—C21 | 1.389 (3) |
C8—N2 | 1.427 (3) | C20—H20 | 0.9300 |
C9—C10 | 1.431 (3) | C21—H21 | 0.9300 |
C9—BR1 | 1.8712 (19) | N1—H1 | 0.8600 |
C10—C11 | 1.392 (3) | N2—S1 | 1.6799 (15) |
C10—C15 | 1.397 (3) | O1—S1 | 1.4215 (17) |
C11—C12 | 1.392 (3) | O2—S1 | 1.4324 (17) |
C11—N2 | 1.427 (2) | ||
C6—C1—F1 | 118.9 (2) | C14—C13—C12 | 122.5 (2) |
C6—C1—C2 | 122.2 (2) | C14—C13—H13 | 118.7 |
F1—C1—C2 | 118.9 (2) | C12—C13—H13 | 118.7 |
C1—C2—C3 | 119.1 (2) | C15—C14—C13 | 120.5 (2) |
C1—C2—H2 | 120.4 | C15—C14—H14 | 119.8 |
C3—C2—H2 | 120.4 | C13—C14—H14 | 119.8 |
C4—C3—C2 | 120.8 (2) | C14—C15—C10 | 118.5 (2) |
C4—C3—H3 | 119.6 | C14—C15—H15 | 120.7 |
C2—C3—H3 | 119.6 | C10—C15—H15 | 120.7 |
C3—C4—C5 | 117.71 (19) | C17—C16—C21 | 121.15 (18) |
C3—C4—N1 | 123.4 (2) | C17—C16—S1 | 118.91 (15) |
C5—C4—N1 | 118.8 (2) | C21—C16—S1 | 119.94 (15) |
C6—C5—C4 | 121.6 (2) | C16—C17—C18 | 119.11 (19) |
C6—C5—H5 | 119.2 | C16—C17—H17 | 120.4 |
C4—C5—H5 | 119.2 | C18—C17—H17 | 120.4 |
C1—C6—C5 | 118.5 (2) | C19—C18—C17 | 120.2 (2) |
C1—C6—H6 | 120.7 | C19—C18—H18 | 119.9 |
C5—C6—H6 | 120.7 | C17—C18—H18 | 119.9 |
N1—C7—C8 | 114.88 (17) | C20—C19—C18 | 120.40 (19) |
N1—C7—H7A | 108.5 | C20—C19—H19 | 119.8 |
C8—C7—H7A | 108.5 | C18—C19—H19 | 119.8 |
N1—C7—H7B | 108.5 | C19—C20—C21 | 120.4 (2) |
C8—C7—H7B | 108.5 | C19—C20—H20 | 119.8 |
H7A—C7—H7B | 107.5 | C21—C20—H20 | 119.8 |
C9—C8—N2 | 107.46 (17) | C16—C21—C20 | 118.8 (2) |
C9—C8—C7 | 128.96 (19) | C16—C21—H21 | 120.6 |
N2—C8—C7 | 123.22 (18) | C20—C21—H21 | 120.6 |
C8—C9—C10 | 110.49 (17) | C4—N1—C7 | 121.22 (18) |
C8—C9—BR1 | 125.55 (16) | C4—N1—H1 | 119.4 |
C10—C9—BR1 | 123.88 (14) | C7—N1—H1 | 119.4 |
C11—C10—C15 | 120.12 (19) | C11—N2—C8 | 107.49 (15) |
C11—C10—C9 | 106.54 (16) | C11—N2—S1 | 120.22 (13) |
C15—C10—C9 | 133.28 (19) | C8—N2—S1 | 122.79 (13) |
C12—C11—C10 | 121.47 (18) | O1—S1—O2 | 119.87 (10) |
C12—C11—N2 | 130.41 (18) | O1—S1—N2 | 106.12 (9) |
C10—C11—N2 | 108.01 (16) | O2—S1—N2 | 106.04 (9) |
C13—C12—C11 | 116.9 (2) | O1—S1—C16 | 109.28 (10) |
C13—C12—H12 | 121.6 | O2—S1—C16 | 109.01 (9) |
C11—C12—H12 | 121.6 | N2—S1—C16 | 105.53 (8) |
C6—C1—C2—C3 | −0.5 (3) | C21—C16—C17—C18 | 1.2 (3) |
F1—C1—C2—C3 | 179.51 (19) | S1—C16—C17—C18 | −178.91 (17) |
C1—C2—C3—C4 | 0.4 (3) | C16—C17—C18—C19 | −0.7 (3) |
C2—C3—C4—C5 | −1.0 (3) | C17—C18—C19—C20 | 0.3 (3) |
C2—C3—C4—N1 | 175.91 (18) | C18—C19—C20—C21 | −0.5 (4) |
C3—C4—C5—C6 | 1.6 (3) | C17—C16—C21—C20 | −1.4 (3) |
N1—C4—C5—C6 | −175.4 (2) | S1—C16—C21—C20 | 178.72 (17) |
F1—C1—C6—C5 | −178.9 (2) | C19—C20—C21—C16 | 1.1 (3) |
C2—C1—C6—C5 | 1.0 (4) | C3—C4—N1—C7 | 21.2 (3) |
C4—C5—C6—C1 | −1.6 (4) | C5—C4—N1—C7 | −162.0 (2) |
N1—C7—C8—C9 | −118.5 (2) | C8—C7—N1—C4 | 66.9 (3) |
N1—C7—C8—N2 | 53.7 (3) | C12—C11—N2—C8 | 176.79 (19) |
N2—C8—C9—C10 | 0.9 (2) | C10—C11—N2—C8 | 0.68 (19) |
C7—C8—C9—C10 | 174.02 (18) | C12—C11—N2—S1 | −36.0 (3) |
N2—C8—C9—BR1 | −176.08 (12) | C10—C11—N2—S1 | 147.90 (13) |
C7—C8—C9—BR1 | −3.0 (3) | C9—C8—N2—C11 | −0.97 (19) |
C8—C9—C10—C11 | −0.5 (2) | C7—C8—N2—C11 | −174.58 (16) |
BR1—C9—C10—C11 | 176.56 (13) | C9—C8—N2—S1 | −147.16 (14) |
C8—C9—C10—C15 | −177.6 (2) | C7—C8—N2—S1 | 39.2 (2) |
BR1—C9—C10—C15 | −0.6 (3) | C11—N2—S1—O1 | 47.52 (16) |
C15—C10—C11—C12 | 0.9 (3) | C8—N2—S1—O1 | −170.39 (15) |
C9—C10—C11—C12 | −176.67 (17) | C11—N2—S1—O2 | 176.02 (14) |
C15—C10—C11—N2 | 177.44 (16) | C8—N2—S1—O2 | −41.89 (17) |
C9—C10—C11—N2 | −0.15 (19) | C11—N2—S1—C16 | −68.41 (15) |
C10—C11—C12—C13 | −0.8 (3) | C8—N2—S1—C16 | 73.69 (16) |
N2—C11—C12—C13 | −176.45 (18) | C17—C16—S1—O1 | −20.95 (18) |
C11—C12—C13—C14 | 0.1 (3) | C21—C16—S1—O1 | 158.89 (16) |
C12—C13—C14—C15 | 0.5 (3) | C17—C16—S1—O2 | −153.69 (16) |
C13—C14—C15—C10 | −0.4 (3) | C21—C16—S1—O2 | 26.15 (18) |
C11—C10—C15—C14 | −0.3 (3) | C17—C16—S1—N2 | 92.79 (16) |
C9—C10—C15—C14 | 176.5 (2) | C21—C16—S1—N2 | −87.37 (17) |
Cg2 and Cg4 are the centroids of rings C1-C6 and C16–C21, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···Br1 | 0.93 | 2.92 | 3.765 (2) | 151 |
C12—H12···O1 | 0.93 | 2.38 | 2.957 (3) | 120 |
C13—H13···Cg2i | 0.93 | 2.90 | 3.8382 (3) | 151 |
C15—H15···Cg4ii | 0.93 | 2.72 | 3.6522 (2) | 154 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+2, −z+1. |
Acknowledgements
CSY thanks VIT University for support. The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection.
References
Bassindale, A. (1984). The Third Dimension in Organic Chemistry, ch. 1, p. 11. New York: John Wiley and Sons. Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
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. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sharma, V., Kumar, P. & Pathak, D. (2010). J. Heterocycl. Chem. 47, 491–502. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef 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.