In the title compound, the indole ring system makes the dihedral angles of 84.89 (7) and 57.32 (5)° with the phenyl rings. In the crystal, molecules are linked by C—H⋯O hydrogen bonds.
Keywords: Indole derivative, crystal structure, C—H⋯O hydrogen bonds
Abstract
In the title compound, C22H17NO3S, the sulfonyl-bound phenyl ring is almost orthogonal to the indole ring system, making a dihedral angle of 84.89 (7)°. The carbonyl-bound phenyl ring forms a dihedral angle of 57.32 (5)° with the indole ring system. The two phenyl rings are inclined at 52.68 (7)°. The S atom has a distorted tetrahedral configuration. In the crystal, weak C—H⋯O interactions link the molecules, forming a helical chain along the b-axis direction.
Chemical context
In a continuation of our studies on indole derivatives, which possess various biological activities such as antihepatitis B virus (Chai et al., 2006 ▸) and antibacterial (Nieto et al., 2005 ▸) etc, we herein report the synthesis and the crystal structure of the title compound, (I).
Structural commentary
The molecular structure of the title compound is shown in Fig. 1 ▸. The sulfonyl-bound phenyl ring (C1–C6) is almost orthogonal to the indole ring system (N1/C7–C14), making a dihedral angle of 84.89 (7)°. The carbonyl-bound phenyl ring (C17–C22) forms a dihedral angle of 57.32 (5)° with the indole ring system. The two phenyl rings are inclined at an angle of 52.68 (7)°. Atom S1 has a distorted tetrahedral configuration with angles O1—S1—O2 [119.97 (10)°] and N1—S1—C1 [104.99 (8)°] differing from the ideal tetrahedral value. As a result of the electron-withdrawing character of the phenylsulfonyl group, the bond lengths N1—C7 [1.420 (2) Å] and N1—C14 [1.419 (2) Å] are longer than the mean value of 1.355 (14) Å (Allen et al., 1987 ▸). The geometric parameters of (I) agree well with those in similar reported structures (Chakkaravarthi et al., 2008 ▸, 2009 ▸).
Figure 1.
The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Supramolecular features
In the crystal, weak C—H⋯O interactions link the molecules, forming a helical chain along the b-axis direction (Table 1 ▸ and Fig. 2 ▸). No significant π–π or C—H⋯π interactions are observed.
Table 1. Hydrogen-bond geometry (, ).
| DHA | DH | HA | D A | DHA |
|---|---|---|---|---|
| C15H15CO1i | 0.96 | 2.59 | 3.525(3) | 165 |
Symmetry code: (i) 
.
Figure 2.
The packing diagram of the title compound, viewed down the a axis. Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
Database survey
A search of the Cambridge Structural Database (Version 5.35, last update May 2014; Groom & Allen, 2014 ▸). indicated 123 compounds having a phenylsulfonyl-1H-indole moiety. Of these compounds, several similar structures have been reported earlier, i.e. ethyl 2-acetoxymethyl-1-phenylsulfonyl-1H-indole-3-carboxylate (Gunasekaran et al., 2009 ▸), 3-iodo-2-methyl-1-phenylsulfonyl-1H-indole (Ramathilagam et al., 2011 ▸) and 1-(2-bromomethyl-1-phenylsulfonyl-1H-indol-3-yl)propan-1-one (Umadevi et al., 2013 ▸). In these structures, the sulfonyl-bound phenyl ring is almost orthogonal to the indole ring system, the dihedral angles of 83.35 (5), 82.84 (9) and 89.91 (11)°, respectively, being are comparable with that in the title compound.
Synthesis and crystallization
To a solution of benzoyl chloride (1.55 g, 11.07 mmol) in dry DCM (25 ml), SnCl4 (2.88 g, 10.10 mmol) at 273 K was added dropwise. To this, phenylsulfonyl-1H-indole (2 g, 7.38 mmol) in dry DCM (10 ml) was added dropwise (5 min) and stirred for 30 min at the same temperature. After completion of the reaction (monitored by TLC), it was poured over ice–water (50 ml) and extracted with saturated aqueous NaHCO3 (2 × 30 ml) and brine (2 × 30 ml), dried (Na2SO4) and concentrated under reduced pressure. Then, the crude product was crystallized from methanol to afford single crystals of the title compound suitable for X-ray diffraction.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. H atoms for Caromatic and Cmethyl were positioned geometrically and refined using a riding model, with C—H = 0.93 and 0.97 Å, respectively 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 | C22H17NO3S |
| M r | 375.43 |
| Crystal system, space group | Orthorhombic, P212121 |
| Temperature (K) | 295 |
| a, b, c () | 8.9989(7), 11.0036(9), 18.4209(16) |
| V (3) | 1824.0(3) |
| Z | 4 |
| Radiation type | Mo K |
| (mm1) | 0.20 |
| Crystal size (mm) | 0.28 0.24 0.20 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Sheldrick, 1996 ▸) |
| T min, T max | 0.946, 0.961 |
| No. of measured, independent and observed [I > 2(I)] reflections | 26244, 5020, 3493 |
| R int | 0.034 |
| (sin /)max (1) | 0.708 |
| Refinement | |
| R[F 2 > 2(F 2)], wR(F 2), S | 0.036, 0.091, 1.02 |
| No. of reflections | 5020 |
| No. of parameters | 246 |
| H-atom treatment | H-atom parameters constrained |
| max, min (e 3) | 0.17, 0.25 |
| Absolute structure | Flack (1983 ▸), 2109 Friedel pairs |
| Absolute structure parameter | 0.01(7) |
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014028059/is5387sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014028059/is5387Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989014028059/is5387Isup3.cml
CCDC reference: 1040926
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors wish to acknowledge the SAIF, IIT, Madras, for the data collection.
supplementary crystallographic information
Crystal data
| C22H17NO3S | F(000) = 784 |
| Mr = 375.43 | Dx = 1.367 Mg m−3 |
| Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 812 reflections |
| a = 8.9989 (7) Å | θ = 2.2–30.2° |
| b = 11.0036 (9) Å | µ = 0.20 mm−1 |
| c = 18.4209 (16) Å | T = 295 K |
| V = 1824.0 (3) Å3 | Block, colourless |
| Z = 4 | 0.28 × 0.24 × 0.20 mm |
Data collection
| Bruker APEXII CCD diffractometer | 5020 independent reflections |
| Radiation source: fine-focus sealed tube | 3493 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.034 |
| ω and φ scan | θmax = 30.2°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
| Tmin = 0.946, Tmax = 0.961 | k = −14→14 |
| 26244 measured reflections | l = −25→24 |
Refinement
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.0353P)2 + 0.2764P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.091 | (Δ/σ)max < 0.001 |
| S = 1.02 | Δρmax = 0.17 e Å−3 |
| 5020 reflections | Δρmin = −0.25 e Å−3 |
| 246 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 0 restraints | Extinction coefficient: 0.0039 (8) |
| Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 2109 Friedel pairs |
| Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.01 (7) |
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. |
| 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 > 2sigma(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.2369 (2) | 0.81475 (17) | 0.72517 (9) | 0.0469 (4) | |
| C2 | 0.2009 (3) | 0.69315 (19) | 0.72539 (12) | 0.0623 (6) | |
| H2 | 0.1029 | 0.6684 | 0.7318 | 0.075* | |
| C3 | 0.3119 (4) | 0.6089 (2) | 0.71605 (14) | 0.0779 (8) | |
| H3 | 0.2891 | 0.5265 | 0.7160 | 0.093* | |
| C4 | 0.4552 (4) | 0.6457 (3) | 0.70682 (13) | 0.0797 (8) | |
| H4 | 0.5295 | 0.5881 | 0.6999 | 0.096* | |
| C5 | 0.4904 (3) | 0.7661 (3) | 0.70759 (15) | 0.0815 (8) | |
| H5 | 0.5889 | 0.7903 | 0.7025 | 0.098* | |
| C6 | 0.3812 (3) | 0.8512 (2) | 0.71586 (13) | 0.0658 (6) | |
| H6 | 0.4047 | 0.9335 | 0.7152 | 0.079* | |
| C7 | 0.1037 (2) | 1.05176 (15) | 0.60528 (9) | 0.0405 (4) | |
| C8 | 0.0471 (2) | 1.03514 (16) | 0.53755 (10) | 0.0417 (4) | |
| C9 | −0.0431 (2) | 0.92698 (17) | 0.53745 (10) | 0.0421 (4) | |
| C10 | −0.1247 (2) | 0.86956 (18) | 0.48385 (12) | 0.0566 (5) | |
| H10 | −0.1258 | 0.8998 | 0.4367 | 0.068* | |
| C11 | −0.2046 (3) | 0.7663 (2) | 0.50152 (15) | 0.0667 (6) | |
| H11 | −0.2593 | 0.7266 | 0.4659 | 0.080* | |
| C12 | −0.2040 (3) | 0.72186 (19) | 0.57128 (15) | 0.0651 (6) | |
| H12 | −0.2588 | 0.6524 | 0.5819 | 0.078* | |
| C13 | −0.1248 (2) | 0.77715 (17) | 0.62583 (13) | 0.0549 (5) | |
| H13 | −0.1251 | 0.7466 | 0.6729 | 0.066* | |
| C14 | −0.0439 (2) | 0.88084 (16) | 0.60774 (11) | 0.0429 (4) | |
| C15 | 0.2119 (2) | 1.14443 (19) | 0.63034 (11) | 0.0521 (5) | |
| H15A | 0.2445 | 1.1921 | 0.5897 | 0.078* | |
| H15B | 0.2959 | 1.1047 | 0.6520 | 0.078* | |
| H15C | 0.1654 | 1.1964 | 0.6655 | 0.078* | |
| C16 | 0.0714 (2) | 1.10898 (16) | 0.47141 (10) | 0.0462 (4) | |
| C17 | 0.0621 (2) | 1.24405 (16) | 0.47428 (10) | 0.0425 (4) | |
| C18 | −0.0098 (2) | 1.30428 (18) | 0.52995 (12) | 0.0513 (5) | |
| H18 | −0.0503 | 1.2605 | 0.5683 | 0.062* | |
| C19 | −0.0215 (3) | 1.4297 (2) | 0.52874 (14) | 0.0667 (6) | |
| H19 | −0.0699 | 1.4700 | 0.5663 | 0.080* | |
| C20 | 0.0380 (3) | 1.4945 (2) | 0.47233 (15) | 0.0684 (7) | |
| H20 | 0.0296 | 1.5787 | 0.4716 | 0.082* | |
| C21 | 0.1096 (3) | 1.4360 (2) | 0.41704 (13) | 0.0633 (6) | |
| H21 | 0.1511 | 1.4805 | 0.3792 | 0.076* | |
| C22 | 0.1204 (2) | 1.31043 (19) | 0.41723 (11) | 0.0512 (5) | |
| H22 | 0.1671 | 1.2707 | 0.3789 | 0.061* | |
| N1 | 0.04557 (17) | 0.95902 (13) | 0.65071 (8) | 0.0436 (4) | |
| O1 | −0.02677 (18) | 0.87038 (14) | 0.76860 (8) | 0.0700 (4) | |
| O2 | 0.16072 (19) | 1.03169 (12) | 0.76515 (8) | 0.0632 (4) | |
| O3 | 0.0922 (2) | 1.05764 (13) | 0.41366 (7) | 0.0699 (4) | |
| S1 | 0.09803 (6) | 0.92484 (4) | 0.73525 (3) | 0.04934 (14) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0585 (12) | 0.0484 (10) | 0.0339 (9) | 0.0054 (9) | 0.0015 (9) | 0.0024 (9) |
| C2 | 0.0712 (14) | 0.0513 (12) | 0.0644 (14) | 0.0075 (11) | −0.0075 (12) | 0.0094 (11) |
| C3 | 0.103 (2) | 0.0516 (14) | 0.0789 (17) | 0.0201 (14) | −0.0139 (16) | −0.0001 (12) |
| C4 | 0.098 (2) | 0.0856 (19) | 0.0556 (14) | 0.0464 (17) | −0.0027 (14) | −0.0015 (13) |
| C5 | 0.0655 (17) | 0.095 (2) | 0.0836 (19) | 0.0196 (15) | 0.0100 (14) | 0.0062 (16) |
| C6 | 0.0626 (14) | 0.0606 (13) | 0.0743 (15) | 0.0054 (12) | 0.0048 (12) | −0.0017 (11) |
| C7 | 0.0405 (9) | 0.0364 (9) | 0.0448 (9) | 0.0027 (8) | 0.0077 (8) | 0.0009 (7) |
| C8 | 0.0453 (10) | 0.0362 (9) | 0.0436 (10) | 0.0040 (8) | 0.0065 (8) | −0.0015 (8) |
| C9 | 0.0441 (9) | 0.0346 (9) | 0.0476 (10) | 0.0067 (8) | 0.0068 (8) | −0.0029 (8) |
| C10 | 0.0608 (13) | 0.0529 (11) | 0.0560 (12) | −0.0004 (11) | 0.0006 (11) | −0.0103 (10) |
| C11 | 0.0660 (15) | 0.0526 (13) | 0.0813 (16) | −0.0068 (11) | 0.0007 (13) | −0.0177 (12) |
| C12 | 0.0555 (14) | 0.0402 (11) | 0.0995 (19) | −0.0051 (10) | 0.0087 (13) | −0.0040 (12) |
| C13 | 0.0497 (12) | 0.0417 (10) | 0.0732 (13) | 0.0019 (10) | 0.0084 (11) | 0.0106 (10) |
| C14 | 0.0395 (9) | 0.0350 (9) | 0.0541 (11) | 0.0043 (8) | 0.0071 (8) | 0.0014 (8) |
| C15 | 0.0556 (12) | 0.0503 (11) | 0.0505 (11) | −0.0049 (10) | 0.0045 (10) | 0.0007 (9) |
| C16 | 0.0526 (12) | 0.0440 (10) | 0.0422 (10) | 0.0019 (9) | 0.0055 (9) | 0.0012 (8) |
| C17 | 0.0403 (10) | 0.0430 (10) | 0.0443 (10) | −0.0004 (8) | −0.0011 (8) | 0.0036 (8) |
| C18 | 0.0530 (12) | 0.0469 (11) | 0.0539 (12) | 0.0055 (9) | 0.0062 (10) | 0.0011 (10) |
| C19 | 0.0682 (14) | 0.0498 (12) | 0.0821 (16) | 0.0095 (12) | −0.0013 (13) | −0.0096 (13) |
| C20 | 0.0693 (15) | 0.0408 (11) | 0.095 (2) | −0.0042 (11) | −0.0175 (15) | 0.0054 (13) |
| C21 | 0.0614 (13) | 0.0547 (12) | 0.0736 (14) | −0.0124 (12) | −0.0097 (12) | 0.0233 (12) |
| C22 | 0.0468 (11) | 0.0554 (12) | 0.0512 (11) | −0.0008 (10) | −0.0007 (9) | 0.0098 (9) |
| N1 | 0.0454 (9) | 0.0403 (8) | 0.0452 (8) | 0.0020 (7) | 0.0056 (7) | 0.0064 (7) |
| O1 | 0.0734 (10) | 0.0768 (10) | 0.0599 (9) | 0.0050 (8) | 0.0309 (8) | 0.0169 (8) |
| O2 | 0.0924 (11) | 0.0505 (8) | 0.0466 (8) | 0.0073 (7) | 0.0019 (8) | −0.0101 (7) |
| O3 | 0.1119 (13) | 0.0526 (8) | 0.0453 (8) | 0.0015 (10) | 0.0186 (9) | −0.0054 (7) |
| S1 | 0.0614 (3) | 0.0477 (3) | 0.0389 (2) | 0.0074 (2) | 0.0117 (2) | 0.0022 (2) |
Geometric parameters (Å, º)
| C1—C6 | 1.369 (3) | C12—H12 | 0.9300 |
| C1—C2 | 1.377 (3) | C13—C14 | 1.394 (3) |
| C1—S1 | 1.750 (2) | C13—H13 | 0.9300 |
| C2—C3 | 1.373 (3) | C14—N1 | 1.419 (2) |
| C2—H2 | 0.9300 | C15—H15A | 0.9600 |
| C3—C4 | 1.362 (4) | C15—H15B | 0.9600 |
| C3—H3 | 0.9300 | C15—H15C | 0.9600 |
| C4—C5 | 1.363 (4) | C16—O3 | 1.219 (2) |
| C4—H4 | 0.9300 | C16—C17 | 1.490 (3) |
| C5—C6 | 1.366 (3) | C17—C18 | 1.382 (3) |
| C5—H5 | 0.9300 | C17—C22 | 1.383 (3) |
| C6—H6 | 0.9300 | C18—C19 | 1.384 (3) |
| C7—C8 | 1.360 (2) | C18—H18 | 0.9300 |
| C7—N1 | 1.420 (2) | C19—C20 | 1.369 (3) |
| C7—C15 | 1.483 (3) | C19—H19 | 0.9300 |
| C8—C9 | 1.441 (3) | C20—C21 | 1.366 (3) |
| C8—C16 | 1.481 (2) | C20—H20 | 0.9300 |
| C9—C10 | 1.383 (3) | C21—C22 | 1.385 (3) |
| C9—C14 | 1.391 (3) | C21—H21 | 0.9300 |
| C10—C11 | 1.384 (3) | C22—H22 | 0.9300 |
| C10—H10 | 0.9300 | N1—S1 | 1.6701 (16) |
| C11—C12 | 1.375 (4) | O1—S1 | 1.4134 (15) |
| C11—H11 | 0.9300 | O2—S1 | 1.4156 (15) |
| C12—C13 | 1.374 (3) | ||
| C6—C1—C2 | 120.5 (2) | C9—C14—C13 | 121.60 (19) |
| C6—C1—S1 | 119.18 (17) | C9—C14—N1 | 107.17 (16) |
| C2—C1—S1 | 120.28 (17) | C13—C14—N1 | 131.22 (19) |
| C3—C2—C1 | 119.0 (2) | C7—C15—H15A | 109.5 |
| C3—C2—H2 | 120.5 | C7—C15—H15B | 109.5 |
| C1—C2—H2 | 120.5 | H15A—C15—H15B | 109.5 |
| C4—C3—C2 | 120.3 (2) | C7—C15—H15C | 109.5 |
| C4—C3—H3 | 119.9 | H15A—C15—H15C | 109.5 |
| C2—C3—H3 | 119.9 | H15B—C15—H15C | 109.5 |
| C3—C4—C5 | 120.5 (3) | O3—C16—C8 | 119.11 (16) |
| C3—C4—H4 | 119.7 | O3—C16—C17 | 120.13 (17) |
| C5—C4—H4 | 119.7 | C8—C16—C17 | 120.66 (16) |
| C4—C5—C6 | 120.0 (3) | C18—C17—C22 | 119.23 (18) |
| C4—C5—H5 | 120.0 | C18—C17—C16 | 122.10 (17) |
| C6—C5—H5 | 120.0 | C22—C17—C16 | 118.58 (17) |
| C5—C6—C1 | 119.7 (2) | C17—C18—C19 | 120.1 (2) |
| C5—C6—H6 | 120.1 | C17—C18—H18 | 119.9 |
| C1—C6—H6 | 120.1 | C19—C18—H18 | 119.9 |
| C8—C7—N1 | 107.82 (15) | C20—C19—C18 | 120.1 (2) |
| C8—C7—C15 | 128.60 (16) | C20—C19—H19 | 120.0 |
| N1—C7—C15 | 123.54 (16) | C18—C19—H19 | 120.0 |
| C7—C8—C9 | 108.87 (16) | C21—C20—C19 | 120.3 (2) |
| C7—C8—C16 | 128.73 (17) | C21—C20—H20 | 119.8 |
| C9—C8—C16 | 122.38 (17) | C19—C20—H20 | 119.8 |
| C10—C9—C14 | 119.69 (18) | C20—C21—C22 | 120.1 (2) |
| C10—C9—C8 | 132.63 (18) | C20—C21—H21 | 120.0 |
| C14—C9—C8 | 107.64 (17) | C22—C21—H21 | 120.0 |
| C9—C10—C11 | 118.9 (2) | C17—C22—C21 | 120.1 (2) |
| C9—C10—H10 | 120.6 | C17—C22—H22 | 119.9 |
| C11—C10—H10 | 120.6 | C21—C22—H22 | 119.9 |
| C12—C11—C10 | 120.6 (2) | C14—N1—C7 | 108.41 (14) |
| C12—C11—H11 | 119.7 | C14—N1—S1 | 122.94 (12) |
| C10—C11—H11 | 119.7 | C7—N1—S1 | 127.40 (13) |
| C13—C12—C11 | 121.9 (2) | O1—S1—O2 | 119.97 (10) |
| C13—C12—H12 | 119.1 | O1—S1—N1 | 106.03 (10) |
| C11—C12—H12 | 119.1 | O2—S1—N1 | 106.76 (8) |
| C12—C13—C14 | 117.3 (2) | O1—S1—C1 | 108.67 (10) |
| C12—C13—H13 | 121.4 | O2—S1—C1 | 109.36 (10) |
| C14—C13—H13 | 121.4 | N1—S1—C1 | 104.99 (8) |
| C6—C1—C2—C3 | −0.1 (3) | C8—C16—C17—C18 | −19.3 (3) |
| S1—C1—C2—C3 | 178.83 (18) | O3—C16—C17—C22 | −19.3 (3) |
| C1—C2—C3—C4 | 0.1 (4) | C8—C16—C17—C22 | 164.22 (18) |
| C2—C3—C4—C5 | 0.8 (4) | C22—C17—C18—C19 | −0.6 (3) |
| C3—C4—C5—C6 | −1.6 (4) | C16—C17—C18—C19 | −177.1 (2) |
| C4—C5—C6—C1 | 1.6 (4) | C17—C18—C19—C20 | 0.0 (3) |
| C2—C1—C6—C5 | −0.8 (3) | C18—C19—C20—C21 | −0.2 (4) |
| S1—C1—C6—C5 | −179.70 (19) | C19—C20—C21—C22 | 1.0 (4) |
| N1—C7—C8—C9 | −2.92 (19) | C18—C17—C22—C21 | 1.4 (3) |
| C15—C7—C8—C9 | 174.62 (18) | C16—C17—C22—C21 | 178.01 (19) |
| N1—C7—C8—C16 | 178.71 (17) | C20—C21—C22—C17 | −1.6 (3) |
| C15—C7—C8—C16 | −3.8 (3) | C9—C14—N1—C7 | −1.39 (19) |
| C7—C8—C9—C10 | −179.9 (2) | C13—C14—N1—C7 | 179.84 (19) |
| C16—C8—C9—C10 | −1.4 (3) | C9—C14—N1—S1 | −169.49 (12) |
| C7—C8—C9—C14 | 2.1 (2) | C13—C14—N1—S1 | 11.7 (3) |
| C16—C8—C9—C14 | −179.42 (16) | C8—C7—N1—C14 | 2.70 (19) |
| C14—C9—C10—C11 | −0.5 (3) | C15—C7—N1—C14 | −174.99 (17) |
| C8—C9—C10—C11 | −178.31 (19) | C8—C7—N1—S1 | 170.12 (13) |
| C9—C10—C11—C12 | 0.5 (3) | C15—C7—N1—S1 | −7.6 (2) |
| C10—C11—C12—C13 | −0.1 (4) | C14—N1—S1—O1 | −40.28 (16) |
| C11—C12—C13—C14 | −0.1 (3) | C7—N1—S1—O1 | 153.97 (15) |
| C10—C9—C14—C13 | 0.2 (3) | C14—N1—S1—O2 | −169.29 (14) |
| C8—C9—C14—C13 | 178.55 (17) | C7—N1—S1—O2 | 24.96 (17) |
| C10—C9—C14—N1 | −178.67 (16) | C14—N1—S1—C1 | 74.67 (16) |
| C8—C9—C14—N1 | −0.37 (19) | C7—N1—S1—C1 | −91.08 (16) |
| C12—C13—C14—C9 | 0.1 (3) | C6—C1—S1—O1 | −159.68 (17) |
| C12—C13—C14—N1 | 178.71 (19) | C2—C1—S1—O1 | 21.40 (19) |
| C7—C8—C16—O3 | 137.3 (2) | C6—C1—S1—O2 | −27.02 (19) |
| C9—C8—C16—O3 | −40.9 (3) | C2—C1—S1—O2 | 154.07 (17) |
| C7—C8—C16—C17 | −46.2 (3) | C6—C1—S1—N1 | 87.22 (18) |
| C9—C8—C16—C17 | 135.63 (18) | C2—C1—S1—N1 | −91.69 (17) |
| O3—C16—C17—C18 | 157.2 (2) |
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| C15—H15C···O1i | 0.96 | 2.59 | 3.525 (3) | 165 |
Symmetry code: (i) −x, y+1/2, −z+3/2.
References
- Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin. Trans. 2, pp. S1–19.
- Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
- Chai, H., Zhao, C., Zhao, C. & Gong, P. (2006). Bioorg. Med. Chem. 14, 911–917. [DOI] [PubMed]
- Chakkaravarthi, G., Marx, A., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2009). Acta Cryst. E65, o464–o465. [DOI] [PMC free article] [PubMed]
- Chakkaravarthi, G., Sureshbabu, R., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o751. [DOI] [PMC free article] [PubMed]
- Flack, H. D. (1983). Acta Cryst. A39, 876–881.
- Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662–671. [DOI] [PubMed]
- Gunasekaran, B., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2069. [DOI] [PMC free article] [PubMed]
- Nieto, M. J., Alovero, F. L., Manzo, R. H. & Mazzieri, M. R. (2005). Eur. J. Med. Chem. 40, 361–369. [DOI] [PubMed]
- Ramathilagam, C., Saravanan, V., Mohanakrishnan, A. K., Chakkaravarthi, G., Umarani, P. R. & Manivannan, V. (2011). Acta Cryst. E67, o632. [DOI] [PMC free article] [PubMed]
- Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
- Umadevi, M., Saravanan, V., Yamuna, R., Mohanakrishnan, A. K. & Chakkaravarthi, G. (2013). Acta Cryst. E69, o1802–o1803. [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) global, I. DOI: 10.1107/S2056989014028059/is5387sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014028059/is5387Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989014028059/is5387Isup3.cml
CCDC reference: 1040926
Additional supporting information: crystallographic information; 3D view; checkCIF report