In the title indole derivative, the chlorophenyl ring is almost perpendicular to the indole moiety, making a dihedral angle of 87.59 (6)°. In the crystal, molecules are linked via C—H⋯π interactions, forming C(9) chains along the [10
] direction.
Keywords: crystal structure, indole, methyl methacrylate, C—H⋯π interactions, π–π interactions
Abstract
In the title indole derivative, C20H18ClNO2, the chlorophenyl ring is almost perpendicular to the indole moiety, making a dihedral angle of 87.6 (1)°. The molecular packing is stabilized by C—H⋯π interactions, which form a C(9) chain motif along [10-1]. In addition, there are weak π–π interactions [centroid–centroid distance 3.851 (1) Å] between the chains, involving inversion-related chlorophenyl rings.
Chemical context
Indole derivatives inhibit hepatitis C virus replication through induction of pro-inflammatory cytokines (Lee et al., 2015 ▸) and these derivatives act as a new anti-hepatitis C virus agents (Andreev et al., 2015 ▸). These derivatives also act as potential mushroom tyrosinase inhibitors (Ferro et al., 2015 ▸). Indole derivatives also exhibit anti-proliferative (Parrino et al., 2015 ▸), anti-inflammatory (Chen et al., 2015 ▸) and anti-tumor (Ma et al., 2015 ▸) activities. In view of the many interesting applications of indole derivatives, we synthesized the title compound and report herein on its crystal structure.
Structural commentary
The molecular structure of the title compound, (I), is illustrated in Fig. 1 ▸. The geometry of the indole ring system (N1/C1–C8) in (I) is comparable with those reported for similar structures, namely 1-vinyl-1H-indole-3-carbaldehyde (II) (Selvanayagam et al., 2008 ▸) and methyl (2Z)-2-[(2-formyl-3-methyl-1H-indol-1-yl)methyl]-3-(4-methoxyphenyl)-prop-2-enoate (III) (Selvanayagam et al., 2014 ▸). The superposition of the indole ring system of (I) with the related reported structures, using Qmol (Gans & Shalloway, 2001 ▸), gives an r.m.s. deviation of 0.025 Å between (I) and (II), and 0.030 Å between (I) and (III); see Fig. 2 ▸. The indole ring system is planar with an r.m.s. deviation of 0.017 Å [maximum deviation of 0.028 (2) Å for atom C3], and the methyl atom C9 deviates by 0.050 (2) Å from its mean plane. The chlorine atom, Cl1, deviates by 0.008 (1) Å from the benzene ring (C15–C20) to which it is attached. This ring is almost perpendicular to the indole ring system, making a dihedral angle of 87.59 (6)°. The sum of the angles at atom N1 of the indole ring (360°) is in accordance with sp 2 hybridization. The widening of the C16—C15—C14 bond angle to 125.2 (1)° is due to the short H⋯H contact (H10B⋯H16 = 2.10 Å). The mean plane of the methyl methacrylate unit [O1/O2/C10–C14; maximum deviation of 0.015 (2) Å for atom O1] is almost planar with the chlrophenyl ring, making a dihedral angle of 18.98 (17)°, but is normal to the indole ring system with a dihedral angle of 89.96 (5)°.
Figure 1.
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
Figure 2.
Superposition of (I) (cyan) with the similar reported structures (II) (yellow; Selvanayagam et al., 2008 ▸) and (III) (green; Selvanayagam et al., 2014 ▸).
Supramolecular features
In the crystal, C—H⋯π interactions link the molecules, forming C(9) chains propagating along [10]; see Fig. 3 ▸ and Table 1 ▸. Between the chains there are weak π–π interactions involving inversion-related chlorophenyl rings (C15–C20), stabilizing the molecular packing [centroid-to-centroid distance = 3.851 (1) Å]; see Fig. 4 ▸.
Figure 3.
The molecular packing of the title compound, viewed along the b axis. C—H⋯π interactions (Table 1 ▸) are shown as dashed lines. For clarity, H atoms not involved in these interactions have been omitted.
Table 1. Hydrogen-bond geometry (, ).
Cg is the centroid of ring C1C6.
| DHA | DH | HA | D A | DHA |
|---|---|---|---|---|
| C13H13A Cg i | 0.96 | 2.69 | 3.581(2) | 154 |
Symmetry code: (i) 
.
Figure 4.
Molecular packing of the title compound, showing the π–π interactions as dashed lines. For clarity, H atoms not involved in these interactions have been omitted.
Synthesis and crystallization
Substituted (Z)-methyl-2-(bromomethyl)-3-phenylacrylate (1 mmol), tetra-butyl-ammonium bromide (0.5 mmol), and 50% NaOH (20 ml) were added to a solution of 3-methyl indole (1 mmol) in benzene (55 ml). The mixture was stirred vigorously at room temperature for 5–6 h. The organic layer was separated, washed with water and dried over MgSO4. The solvent was evaporated under reduced pressure (yield: 70%). Suitable crystals were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. H atoms were placed in idealized positions and allowed to ride on their parent atoms: C—H = 0.93–0.97 Å, with U iso(H) = 1.5U eq(C) for methyl H atoms and 1.2U eq(C) for other H atoms.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C20H18ClNO2 |
| M r | 339.80 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 292 |
| a, b, c () | 9.5867(5), 15.9077(8), 10.8902(6) |
| () | 94.787(1) |
| V (3) | 1654.99(15) |
| Z | 4 |
| Radiation type | Mo K |
| (mm1) | 0.24 |
| Crystal size (mm) | 0.20 0.18 0.16 |
| Data collection | |
| Diffractometer | Bruker SMART APEX CCD area detector |
| No. of measured, independent and observed [I > 2(I)] reflections | 19078, 3944, 3313 |
| R int | 0.026 |
| (sin /)max (1) | 0.661 |
| Refinement | |
| R[F 2 > 2(F 2)], wR(F 2), S | 0.044, 0.127, 1.02 |
| No. of reflections | 3944 |
| No. of parameters | 219 |
| H-atom treatment | H-atom parameters constrained |
| max, min (e 3) | 0.30, 0.23 |
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015010002/su5135sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015010002/su5135Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015010002/su5135Isup3.cml
CCDC reference: 1402521
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
SS thanks the Principal and Management of Kings College of Engineering, Punalkulam, for their support and encouragement.
supplementary crystallographic information
Crystal data
| C20H18ClNO2 | F(000) = 712 |
| Mr = 339.80 | Dx = 1.364 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| a = 9.5867 (5) Å | Cell parameters from 12437 reflections |
| b = 15.9077 (8) Å | θ = 2.3–27.7° |
| c = 10.8902 (6) Å | µ = 0.24 mm−1 |
| β = 94.787 (1)° | T = 292 K |
| V = 1654.99 (15) Å3 | Block, colourless |
| Z = 4 | 0.20 × 0.18 × 0.16 mm |
Data collection
| Bruker SMART APEX CCD area-detector diffractometer | Rint = 0.026 |
| Radiation source: fine-focus sealed tube | θmax = 28.0°, θmin = 2.3° |
| ω scans | h = −12→12 |
| 19078 measured reflections | k = −20→20 |
| 3944 independent reflections | l = −14→14 |
| 3313 reflections with I > 2σ(I) |
Refinement
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
| wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0722P)2 + 0.3404P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.02 | (Δ/σ)max = 0.002 |
| 3944 reflections | Δρmax = 0.30 e Å−3 |
| 219 parameters | Δρmin = −0.23 e Å−3 |
Special details
| 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 0.85221 (5) | 1.06092 (3) | 0.06559 (4) | 0.05976 (16) | |
| O1 | 0.23237 (16) | 0.66473 (11) | −0.05769 (11) | 0.0775 (4) | |
| O2 | 0.21544 (12) | 0.62293 (7) | 0.13579 (10) | 0.0524 (3) | |
| N1 | 0.32743 (12) | 0.78373 (7) | 0.30864 (10) | 0.0366 (3) | |
| C1 | 0.32983 (13) | 0.78740 (8) | 0.43477 (12) | 0.0333 (3) | |
| C2 | 0.40942 (15) | 0.74169 (9) | 0.52459 (13) | 0.0405 (3) | |
| H2 | 0.4756 | 0.7027 | 0.5035 | 0.049* | |
| C3 | 0.38621 (16) | 0.75652 (10) | 0.64588 (13) | 0.0472 (4) | |
| H3 | 0.4365 | 0.7262 | 0.7077 | 0.057* | |
| C4 | 0.28848 (17) | 0.81630 (11) | 0.67783 (13) | 0.0487 (4) | |
| H4 | 0.2759 | 0.8254 | 0.7605 | 0.058* | |
| C5 | 0.21077 (15) | 0.86187 (9) | 0.58952 (13) | 0.0421 (3) | |
| H5 | 0.1468 | 0.9018 | 0.6120 | 0.051* | |
| C6 | 0.22927 (13) | 0.84726 (8) | 0.46513 (12) | 0.0341 (3) | |
| C7 | 0.16518 (14) | 0.87978 (9) | 0.35139 (13) | 0.0384 (3) | |
| C8 | 0.22748 (14) | 0.83989 (9) | 0.25968 (13) | 0.0390 (3) | |
| H8 | 0.2059 | 0.8491 | 0.1759 | 0.047* | |
| C9 | 0.05055 (18) | 0.94375 (11) | 0.33648 (17) | 0.0551 (4) | |
| H9A | 0.0297 | 0.9559 | 0.2506 | 0.083* | |
| H9B | 0.0800 | 0.9943 | 0.3792 | 0.083* | |
| H9C | −0.0316 | 0.9221 | 0.3701 | 0.083* | |
| C10 | 0.41548 (15) | 0.72823 (9) | 0.24128 (12) | 0.0391 (3) | |
| H10A | 0.4063 | 0.6711 | 0.2708 | 0.047* | |
| H10B | 0.5126 | 0.7449 | 0.2578 | 0.047* | |
| C11 | 0.37749 (15) | 0.73022 (9) | 0.10415 (12) | 0.0395 (3) | |
| C12 | 0.26941 (16) | 0.67031 (10) | 0.05008 (14) | 0.0457 (3) | |
| C13 | 0.1091 (2) | 0.56359 (11) | 0.0915 (2) | 0.0622 (5) | |
| H13A | 0.0294 | 0.5934 | 0.0543 | 0.093* | |
| H13B | 0.0815 | 0.5306 | 0.1592 | 0.093* | |
| H13C | 0.1457 | 0.5272 | 0.0316 | 0.093* | |
| C14 | 0.43561 (15) | 0.78067 (10) | 0.02431 (13) | 0.0427 (3) | |
| H14 | 0.4052 | 0.7706 | −0.0577 | 0.051* | |
| C15 | 0.53784 (15) | 0.84850 (9) | 0.04181 (13) | 0.0418 (3) | |
| C16 | 0.57356 (18) | 0.89031 (11) | 0.15350 (14) | 0.0499 (4) | |
| H16 | 0.5315 | 0.8742 | 0.2238 | 0.060* | |
| C17 | 0.66983 (18) | 0.95481 (11) | 0.16082 (15) | 0.0516 (4) | |
| H17 | 0.6930 | 0.9818 | 0.2355 | 0.062* | |
| C18 | 0.73146 (16) | 0.97890 (9) | 0.05648 (14) | 0.0447 (3) | |
| C19 | 0.69899 (19) | 0.93986 (11) | −0.05510 (15) | 0.0521 (4) | |
| H19 | 0.7414 | 0.9567 | −0.1248 | 0.063* | |
| C20 | 0.60262 (18) | 0.87549 (11) | −0.06176 (14) | 0.0495 (4) | |
| H20 | 0.5800 | 0.8492 | −0.1371 | 0.059* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0659 (3) | 0.0532 (3) | 0.0606 (3) | −0.00944 (19) | 0.0072 (2) | 0.00371 (18) |
| O1 | 0.0809 (9) | 0.1119 (12) | 0.0386 (7) | −0.0357 (9) | −0.0008 (6) | −0.0147 (7) |
| O2 | 0.0572 (7) | 0.0500 (6) | 0.0490 (6) | −0.0075 (5) | −0.0016 (5) | −0.0016 (5) |
| N1 | 0.0384 (6) | 0.0420 (6) | 0.0293 (5) | 0.0067 (5) | 0.0016 (4) | −0.0017 (4) |
| C1 | 0.0341 (6) | 0.0353 (6) | 0.0304 (6) | −0.0008 (5) | 0.0024 (5) | −0.0030 (5) |
| C2 | 0.0428 (7) | 0.0411 (7) | 0.0371 (7) | 0.0080 (6) | −0.0005 (6) | −0.0006 (6) |
| C3 | 0.0524 (9) | 0.0538 (9) | 0.0341 (7) | 0.0067 (7) | −0.0031 (6) | 0.0035 (6) |
| C4 | 0.0528 (9) | 0.0641 (10) | 0.0292 (7) | 0.0029 (7) | 0.0041 (6) | −0.0049 (6) |
| C5 | 0.0407 (7) | 0.0468 (8) | 0.0394 (7) | 0.0032 (6) | 0.0070 (6) | −0.0069 (6) |
| C6 | 0.0328 (6) | 0.0344 (6) | 0.0351 (7) | −0.0016 (5) | 0.0025 (5) | −0.0014 (5) |
| C7 | 0.0360 (7) | 0.0397 (7) | 0.0390 (7) | 0.0028 (5) | 0.0013 (5) | 0.0002 (6) |
| C8 | 0.0391 (7) | 0.0446 (7) | 0.0324 (7) | 0.0043 (6) | −0.0010 (5) | 0.0031 (5) |
| C9 | 0.0504 (9) | 0.0552 (10) | 0.0591 (10) | 0.0181 (7) | 0.0013 (7) | 0.0038 (8) |
| C10 | 0.0403 (7) | 0.0446 (7) | 0.0321 (7) | 0.0069 (6) | 0.0016 (5) | −0.0041 (5) |
| C11 | 0.0400 (7) | 0.0478 (8) | 0.0306 (7) | 0.0066 (6) | 0.0019 (5) | −0.0069 (6) |
| C12 | 0.0450 (8) | 0.0538 (9) | 0.0384 (8) | 0.0033 (7) | 0.0034 (6) | −0.0098 (6) |
| C13 | 0.0606 (11) | 0.0505 (9) | 0.0739 (12) | −0.0092 (8) | −0.0043 (9) | −0.0039 (8) |
| C14 | 0.0433 (8) | 0.0540 (8) | 0.0305 (7) | 0.0056 (6) | 0.0007 (6) | −0.0064 (6) |
| C15 | 0.0441 (8) | 0.0463 (8) | 0.0349 (7) | 0.0072 (6) | 0.0024 (6) | −0.0006 (6) |
| C16 | 0.0583 (9) | 0.0570 (9) | 0.0357 (8) | −0.0043 (7) | 0.0108 (7) | −0.0050 (7) |
| C17 | 0.0602 (10) | 0.0545 (9) | 0.0406 (8) | −0.0044 (7) | 0.0075 (7) | −0.0088 (7) |
| C18 | 0.0456 (8) | 0.0406 (8) | 0.0476 (8) | 0.0049 (6) | 0.0024 (6) | 0.0041 (6) |
| C19 | 0.0626 (10) | 0.0563 (10) | 0.0384 (8) | −0.0001 (7) | 0.0095 (7) | 0.0067 (7) |
| C20 | 0.0606 (9) | 0.0555 (9) | 0.0319 (7) | −0.0002 (7) | 0.0015 (6) | −0.0003 (6) |
Geometric parameters (Å, º)
| Cl1—C18 | 1.7417 (16) | C9—H9B | 0.9600 |
| O1—C12 | 1.2007 (19) | C9—H9C | 0.9600 |
| O2—C12 | 1.3370 (19) | C10—C11 | 1.5077 (18) |
| O2—C13 | 1.442 (2) | C10—H10A | 0.9700 |
| N1—C1 | 1.3731 (16) | C10—H10B | 0.9700 |
| N1—C8 | 1.3839 (17) | C11—C14 | 1.338 (2) |
| N1—C10 | 1.4607 (17) | C11—C12 | 1.492 (2) |
| C1—C2 | 1.3940 (19) | C13—H13A | 0.9600 |
| C1—C6 | 1.4138 (18) | C13—H13B | 0.9600 |
| C2—C3 | 1.378 (2) | C13—H13C | 0.9600 |
| C2—H2 | 0.9300 | C14—C15 | 1.460 (2) |
| C3—C4 | 1.399 (2) | C14—H14 | 0.9300 |
| C3—H3 | 0.9300 | C15—C20 | 1.400 (2) |
| C4—C5 | 1.373 (2) | C15—C16 | 1.403 (2) |
| C4—H4 | 0.9300 | C16—C17 | 1.378 (2) |
| C5—C6 | 1.4001 (19) | C16—H16 | 0.9300 |
| C5—H5 | 0.9300 | C17—C18 | 1.378 (2) |
| C6—C7 | 1.4327 (19) | C17—H17 | 0.9300 |
| C7—C8 | 1.363 (2) | C18—C19 | 1.377 (2) |
| C7—C9 | 1.497 (2) | C19—C20 | 1.377 (2) |
| C8—H8 | 0.9300 | C19—H19 | 0.9300 |
| C9—H9A | 0.9600 | C20—H20 | 0.9300 |
| C12—O2—C13 | 116.06 (13) | N1—C10—H10B | 109.1 |
| C1—N1—C8 | 108.14 (11) | C11—C10—H10B | 109.1 |
| C1—N1—C10 | 124.46 (11) | H10A—C10—H10B | 107.8 |
| C8—N1—C10 | 127.39 (11) | C14—C11—C12 | 116.07 (13) |
| N1—C1—C2 | 129.96 (12) | C14—C11—C10 | 125.23 (13) |
| N1—C1—C6 | 107.92 (11) | C12—C11—C10 | 118.67 (13) |
| C2—C1—C6 | 122.09 (12) | O1—C12—O2 | 122.72 (15) |
| C3—C2—C1 | 117.42 (13) | O1—C12—C11 | 124.88 (16) |
| C3—C2—H2 | 121.3 | O2—C12—C11 | 112.39 (12) |
| C1—C2—H2 | 121.3 | O2—C13—H13A | 109.5 |
| C2—C3—C4 | 121.32 (14) | O2—C13—H13B | 109.5 |
| C2—C3—H3 | 119.3 | H13A—C13—H13B | 109.5 |
| C4—C3—H3 | 119.3 | O2—C13—H13C | 109.5 |
| C5—C4—C3 | 121.33 (13) | H13A—C13—H13C | 109.5 |
| C5—C4—H4 | 119.3 | H13B—C13—H13C | 109.5 |
| C3—C4—H4 | 119.3 | C11—C14—C15 | 132.06 (13) |
| C4—C5—C6 | 119.00 (13) | C11—C14—H14 | 114.0 |
| C4—C5—H5 | 120.5 | C15—C14—H14 | 114.0 |
| C6—C5—H5 | 120.5 | C20—C15—C16 | 117.42 (15) |
| C5—C6—C1 | 118.81 (12) | C20—C15—C14 | 117.37 (13) |
| C5—C6—C7 | 134.17 (13) | C16—C15—C14 | 125.19 (14) |
| C1—C6—C7 | 107.01 (11) | C17—C16—C15 | 121.12 (15) |
| C8—C7—C6 | 106.44 (12) | C17—C16—H16 | 119.4 |
| C8—C7—C9 | 126.87 (14) | C15—C16—H16 | 119.4 |
| C6—C7—C9 | 126.68 (13) | C18—C17—C16 | 119.37 (15) |
| C7—C8—N1 | 110.49 (12) | C18—C17—H17 | 120.3 |
| C7—C8—H8 | 124.8 | C16—C17—H17 | 120.3 |
| N1—C8—H8 | 124.8 | C19—C18—C17 | 121.42 (15) |
| C7—C9—H9A | 109.5 | C19—C18—Cl1 | 119.23 (12) |
| C7—C9—H9B | 109.5 | C17—C18—Cl1 | 119.34 (12) |
| H9A—C9—H9B | 109.5 | C18—C19—C20 | 118.89 (15) |
| C7—C9—H9C | 109.5 | C18—C19—H19 | 120.6 |
| H9A—C9—H9C | 109.5 | C20—C19—H19 | 120.6 |
| H9B—C9—H9C | 109.5 | C19—C20—C15 | 121.77 (15) |
| N1—C10—C11 | 112.50 (11) | C19—C20—H20 | 119.1 |
| N1—C10—H10A | 109.1 | C15—C20—H20 | 119.1 |
| C11—C10—H10A | 109.1 | ||
| C8—N1—C1—C2 | 178.13 (14) | C8—N1—C10—C11 | −6.0 (2) |
| C10—N1—C1—C2 | −1.0 (2) | N1—C10—C11—C14 | 92.47 (17) |
| C8—N1—C1—C6 | −0.08 (15) | N1—C10—C11—C12 | −89.24 (16) |
| C10—N1—C1—C6 | −179.21 (12) | C13—O2—C12—O1 | 0.2 (2) |
| N1—C1—C2—C3 | −177.65 (14) | C13—O2—C12—C11 | 179.53 (13) |
| C6—C1—C2—C3 | 0.3 (2) | C14—C11—C12—O1 | 0.0 (2) |
| C1—C2—C3—C4 | −1.2 (2) | C10—C11—C12—O1 | −178.46 (16) |
| C2—C3—C4—C5 | 0.7 (3) | C14—C11—C12—O2 | −179.30 (13) |
| C3—C4—C5—C6 | 0.7 (2) | C10—C11—C12—O2 | 2.25 (19) |
| C4—C5—C6—C1 | −1.5 (2) | C12—C11—C14—C15 | 176.82 (14) |
| C4—C5—C6—C7 | 177.51 (15) | C10—C11—C14—C15 | −4.9 (3) |
| N1—C1—C6—C5 | 179.37 (12) | C11—C14—C15—C20 | 164.77 (16) |
| C2—C1—C6—C5 | 1.0 (2) | C11—C14—C15—C16 | −17.0 (3) |
| N1—C1—C6—C7 | 0.14 (15) | C20—C15—C16—C17 | −0.7 (2) |
| C2—C1—C6—C7 | −178.25 (13) | C14—C15—C16—C17 | −178.87 (15) |
| C5—C6—C7—C8 | −179.20 (15) | C15—C16—C17—C18 | 0.3 (3) |
| C1—C6—C7—C8 | −0.14 (15) | C16—C17—C18—C19 | 0.0 (3) |
| C5—C6—C7—C9 | −0.3 (3) | C16—C17—C18—Cl1 | 179.55 (13) |
| C1—C6—C7—C9 | 178.81 (15) | C17—C18—C19—C20 | 0.1 (3) |
| C6—C7—C8—N1 | 0.09 (16) | Cl1—C18—C19—C20 | −179.51 (13) |
| C9—C7—C8—N1 | −178.86 (14) | C18—C19—C20—C15 | −0.4 (3) |
| C1—N1—C8—C7 | 0.00 (16) | C16—C15—C20—C19 | 0.7 (2) |
| C10—N1—C8—C7 | 179.09 (13) | C14—C15—C20—C19 | 179.06 (15) |
| C1—N1—C10—C11 | 172.92 (13) |
Hydrogen-bond geometry (Å, º)
Cg is the centroid of ring C1–C6.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C13—H13A···Cgi | 0.96 | 2.69 | 3.581 (2) | 154 |
Symmetry code: (i) x−1/2, −y−1/2, z−1/2.
References
- Andreev, I. A., Manvar, D., Barreca, M. L., Belov, D. S., Basu, A., Sweeney, N. L., Ratmanova, N. K., Lukyanenko, E. R., Manfroni, G., Cecchetti, V., Frick, D. N., Altieri, A., Kaushik-Basu, N. & Kurkin, A. V. (2015). Eur. J. Med. Chem. 96, 250–258. [DOI] [PMC free article] [PubMed]
- Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
- Chen, Y. R., Tseng, C. H., Chen, Y. L., Hwang, T. L. & Tzeng, C. C. (2015). Int. J. Mol. Sci. 16, 6532–6544. [DOI] [PMC free article] [PubMed]
- Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
- Ferro, S., Certo, G., De Luca, L., Germano, M. P., Rapisarda, A. & Gitto, R. (2015). J. Enzyme. Inhib. Med. Chem. 31, 1–6. [DOI] [PubMed]
- Gans, J. D. & Shalloway, D. (2001). J. Mol. Graphics Modell. 19, 557–559. [DOI] [PubMed]
- Lee, S., Jin, G., Kim, D., Son, S., Lee, K. & Lee, C. (2015). Acta Virol. 59, 64–77. [DOI] [PubMed]
- Ma, J., Bao, G., Wang, L., Li, W., Xu, B., Du, B., Lv, J., Zhai, X. & Gong, P. (2015). Eur. J. Med. Chem. 96, 173–186. [DOI] [PubMed]
- Parrino, B., Carbone, A., Di Vita, G., Ciancimino, C., Attanzio, A., Spano, V., Montalbano, A., Barraja, P., Tesoriere, L., Livera, M. A., Diana, P. & Cirrincione, G. (2015). Mar. Drugs, 13, 1901–1924. [DOI] [PMC free article] [PubMed]
- Selvanayagam, S., Sridhar, B., Kathiravan, S. & Raghunathan, R. (2014). Acta Cryst. E70, o431–o432. [DOI] [PMC free article] [PubMed]
- Selvanayagam, S., Sridhar, B., Ravikumar, K., Kathiravan, S. & Raghunathan, R. (2008). Acta Cryst. E64, o1163. [DOI] [PMC free article] [PubMed]
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.
- Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015010002/su5135sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015010002/su5135Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015010002/su5135Isup3.cml
CCDC reference: 1402521
Additional supporting information: crystallographic information; 3D view; checkCIF report