organic compounds
1-[(4-Methoxyphenyl)sulfonyl]-1H-indole-3-carbaldehyde
aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India
*Correspondence e-mail: mahendra@physics.uni-mysore.ac.in
In the molecule of the title compound, C16H13NO4S, the mean plane of the indole ring system and that of the methoxyphenyl ring, which are bridged by a sulfonyl group, are inclined at a dihedral angle of 88.98 (9)°. The is stabilized by intermolecular C—H⋯O hydrogen bonds.
Keywords: crystal structure; indole derivative; hydrogen bonding.
CCDC reference: 1449064
Structure description
Indole is a nitrogen-containing bicyclic heteroaromatic compound comprising a six-membered benzene ring fused to a five-membered pyrrole ring. Indole is one of the most important scaffolds in drug discovery and its derivatives are used as commercial drugs for many clinical applications (Zhang et al., 2015) and as key building blocks for the preparation of biological and pharmaceutical agents. For example, they find use in antibacterial screening (El-Sayed et al., 2016), antiviral studies (El-Sayed et al., 2016) and as antitumour (Ma et al., 2015) or antimalarial agents (Santos et al., 2015). We have synthesized the title indole derivative and present its here.
In the molecular structure, the bond lengths (Allen et al., 1987) and angles of the title compound (Fig. 1) are generally within the normal ranges. The indole moiety is bridged by the N-bound sulfonyl group to the methoxyphenyl unit. The planes of the benzene ring and the indole ring system are inclined at 88.98 (9)°. The carbaldehyde and methoxy groups are in antiperiplanar and conformations with respect to the pyrrole and phenyl rings, as indicated by torsion angles of −172.8 (2) (C9—C8—C10—O11) and −1.7 (3)° (C19—C18—C21—C22). A weak intramolecular C3—H3⋯O14 hydrogen bond also affects the conformation of the molecule (Table 1). In the crystal, intermolecular C3—H3⋯O21 hydrogen bonds form chains of molecules along b. Additional C22—H22A⋯O11 contacts further stabilize the packing, stacking molecules along the b-axis direction (Fig. 2).
Synthesis and crystallization
1H-Indole-3-carbaldehyde (3.4 mmol) was dissolved in N,N-dimethylformamide (DMF) and K2CO3 (4.1 mmol) was added. The solution was stirred for 15 min and then 4-methoxybenzenesulfonyl chloride (3.5 mmol) was added portionwise to the ice-cold solution. The reaction continued for 6 h and was monitored by (TLC). On completion, the reaction mixture was diluted with water (50 ml). The aqueous layer was extracted with ethyl acetate (3 × 20 ml) and the combined ethyl acetate layers were washed with brine (2 × 25 ml). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the crude product. This was purified by over silica gel (60–120 mesh) using hexane–ethyl acetate (8:2 v/v) as The pure compound was crystallized from ethyl acetate and hexane as colourless single crystals.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1449064
10.1107/S2414314616001413/sj4009sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616001413/sj4009Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616001413/sj4009Isup3.cml
1H-Indole-3-carbaldehyde (3.4 mmol) was dissolved in N,N-dimethylformamide (DMF) and K2CO3 (4.1 mmol) was added. The solution was stirred for 15 min and then 4-methoxybenzenesulfonyl chloride (3.5 mmol) was added portionwise to the ice-cold solution. The reaction continued for 6 h and was monitored by
(TLC). On completion, the reaction mixture was diluted with water (50 ml). The aqueous layer was extracted with ethyl acetate (3 × 20 ml) and the combined ethyl acetate layers were washed with brine (2 × 25 ml). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the crude product. This was purified by over silica gel (60–120 mesh) using hexane–ethyl acetate (8:2 v/v) as The pure compound was crystallized from ethyl acetate and hexane as colourless single crystals.Indole is a nitrogen-containing bicyclic heteroaromatic compound comprising a six-membered benzene ring fused to a five-membered pyrrole ring. Indole is one of the most important scaffolds in drug discovery and its derivatives are used as commercial drugs for many clinical applications (Zhang et al., 2015) and as key building blocks for the preparation of biological and pharmaceutical agents. For example, they find use in antibacterial screening (El-Sayed et al., 2016), antiviral studies (El-Sayed et al., 2016) and as antitumor (Ma et al., 2015) or antimalarial agents (Santos et al., 2015). We have synthesized the title indole derivative and present its
here.In the molecular structure, the bond lengths (Allen et al., 1987) and angles of the title compound (Fig. 1) are generally within the normal ranges. The indole moiety is bridged by the N-bound sulfonyl group to the methoxyphenyl unit. The planes of the benzene ring and the indole ring system are inclined at 88.98 (9)°. The carbaldehyde and methoxy groups are in antiperiplanar and
conformations with respect to the pyrrole and phenyl rings, as indicated by the torsion angles −172.8 (2) (C9—C8—C10—O11) and −1.7 (3)° (C19—C18—C21—C22). A weak intramolecular C3—H3···O14 hydrogen bond also affects the conformation of the molecule (Table 1). In the crystal, intermolecular C3—H3···O21 hydrogen bonds form chains of molecules along b. Additional C22—H22A···O11 contacts further stabilize the packing, stacking molecules along the b-axis direction (Fig. 2).Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. Perspective diagram of the title molecule, shown with 50% probability displacement ellipsoids. | |
Fig. 2. Packing of the title compound, viewed along the b-axis direction. |
C16H13NO4S | F(000) = 656 |
Mr = 315.34 | Dx = 1.478 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ybc | Cell parameters from 2291 reflections |
a = 6.9942 (7) Å | θ = 6.4–64.3° |
b = 8.2942 (9) Å | µ = 2.20 mm−1 |
c = 24.598 (3) Å | T = 296 K |
β = 96.814 (2)° | Block, colourless |
V = 1416.9 (3) Å3 | 0.30 × 0.25 × 0.20 mm |
Z = 4 |
Bruker X8 Proteum diffractometer | 2220 reflections with I > 2σ(I) |
Radiation source: Bruker MicroStar microfocus rotating anode | Rint = 0.038 |
Helios multilayer optics monochromator | θmax = 64.3°, θmin = 6.4° |
Detector resolution: 10.7 pixels mm-1 | h = −8→8 |
φ and ω scans | k = −9→8 |
10500 measured reflections | l = −28→28 |
2291 independent reflections |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0496P)2 + 1.4084P] where P = (Fo2 + 2Fc2)/3 |
2291 reflections | (Δ/σ)max < 0.001 |
200 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
C16H13NO4S | V = 1416.9 (3) Å3 |
Mr = 315.34 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 6.9942 (7) Å | µ = 2.20 mm−1 |
b = 8.2942 (9) Å | T = 296 K |
c = 24.598 (3) Å | 0.30 × 0.25 × 0.20 mm |
β = 96.814 (2)° |
Bruker X8 Proteum diffractometer | 2220 reflections with I > 2σ(I) |
10500 measured reflections | Rint = 0.038 |
2291 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.22 e Å−3 |
2291 reflections | Δρmin = −0.43 e Å−3 |
200 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S12 | 0.89891 (7) | 0.41020 (6) | 0.42187 (2) | 0.0189 (2) | |
O11 | 0.9913 (2) | 0.4522 (2) | 0.17498 (6) | 0.0352 (5) | |
O13 | 1.0955 (2) | 0.45093 (19) | 0.43860 (6) | 0.0244 (5) | |
O14 | 0.8108 (2) | 0.27610 (18) | 0.44527 (6) | 0.0242 (5) | |
O21 | 0.4462 (2) | 1.00075 (18) | 0.43282 (6) | 0.0245 (5) | |
N1 | 0.8930 (2) | 0.3701 (2) | 0.35443 (7) | 0.0194 (5) | |
C2 | 0.7317 (3) | 0.3124 (2) | 0.31978 (8) | 0.0187 (6) | |
C3 | 0.5632 (3) | 0.2421 (3) | 0.33293 (9) | 0.0218 (6) | |
C4 | 0.4314 (3) | 0.1927 (3) | 0.28930 (9) | 0.0263 (7) | |
C5 | 0.4673 (3) | 0.2143 (3) | 0.23517 (9) | 0.0278 (7) | |
C6 | 0.6348 (3) | 0.2847 (3) | 0.22240 (9) | 0.0253 (7) | |
C7 | 0.7704 (3) | 0.3354 (3) | 0.26557 (8) | 0.0200 (6) | |
C8 | 0.9589 (3) | 0.4099 (3) | 0.26807 (8) | 0.0210 (6) | |
C9 | 1.0265 (3) | 0.4299 (3) | 0.32206 (8) | 0.0202 (6) | |
C10 | 1.0620 (3) | 0.4573 (3) | 0.22269 (9) | 0.0252 (7) | |
C15 | 0.7541 (3) | 0.5802 (3) | 0.42364 (8) | 0.0187 (6) | |
C16 | 0.8295 (3) | 0.7300 (3) | 0.41079 (8) | 0.0219 (6) | |
C17 | 0.7212 (3) | 0.8668 (3) | 0.41341 (8) | 0.0232 (6) | |
C18 | 0.5359 (3) | 0.8571 (3) | 0.42915 (8) | 0.0209 (6) | |
C19 | 0.4582 (3) | 0.7078 (3) | 0.44049 (8) | 0.0211 (6) | |
C20 | 0.5677 (3) | 0.5690 (3) | 0.43757 (8) | 0.0214 (6) | |
C22 | 0.2546 (3) | 1.0020 (3) | 0.44815 (9) | 0.0264 (7) | |
H3 | 0.53960 | 0.22880 | 0.36910 | 0.0260* | |
H4 | 0.31700 | 0.14430 | 0.29640 | 0.0320* | |
H5 | 0.37590 | 0.18020 | 0.20700 | 0.0330* | |
H6 | 0.65720 | 0.29830 | 0.18620 | 0.0300* | |
H9 | 1.14400 | 0.47640 | 0.33510 | 0.0240* | |
H10 | 1.18830 | 0.49330 | 0.23040 | 0.0300* | |
H16 | 0.95290 | 0.73660 | 0.40050 | 0.0260* | |
H17 | 0.77100 | 0.96620 | 0.40470 | 0.0280* | |
H19 | 0.33360 | 0.70120 | 0.45000 | 0.0250* | |
H20 | 0.51650 | 0.46900 | 0.44490 | 0.0260* | |
H22A | 0.16780 | 0.95410 | 0.41950 | 0.0400* | |
H22B | 0.21600 | 1.11110 | 0.45390 | 0.0400* | |
H22C | 0.25190 | 0.94150 | 0.48130 | 0.0400* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S12 | 0.0204 (3) | 0.0209 (3) | 0.0153 (3) | −0.0019 (2) | 0.0015 (2) | 0.0010 (2) |
O11 | 0.0343 (9) | 0.0517 (11) | 0.0205 (8) | 0.0046 (8) | 0.0076 (7) | −0.0002 (7) |
O13 | 0.0192 (7) | 0.0304 (9) | 0.0226 (8) | −0.0017 (6) | −0.0015 (6) | −0.0006 (6) |
O14 | 0.0281 (8) | 0.0224 (8) | 0.0225 (8) | −0.0041 (6) | 0.0050 (6) | 0.0042 (6) |
O21 | 0.0222 (8) | 0.0228 (9) | 0.0297 (8) | 0.0008 (6) | 0.0077 (6) | 0.0027 (6) |
N1 | 0.0191 (8) | 0.0217 (9) | 0.0175 (8) | −0.0026 (7) | 0.0022 (7) | −0.0011 (7) |
C2 | 0.0195 (10) | 0.0148 (10) | 0.0210 (10) | 0.0010 (8) | −0.0006 (8) | −0.0020 (8) |
C3 | 0.0221 (10) | 0.0184 (11) | 0.0251 (11) | −0.0009 (9) | 0.0038 (8) | 0.0001 (8) |
C4 | 0.0205 (11) | 0.0200 (11) | 0.0374 (12) | −0.0030 (9) | −0.0004 (9) | −0.0011 (9) |
C5 | 0.0264 (12) | 0.0231 (12) | 0.0312 (12) | 0.0003 (9) | −0.0076 (9) | −0.0038 (9) |
C6 | 0.0283 (12) | 0.0257 (12) | 0.0207 (10) | 0.0038 (10) | −0.0026 (8) | −0.0012 (9) |
C7 | 0.0219 (10) | 0.0170 (11) | 0.0210 (10) | 0.0045 (9) | 0.0021 (8) | −0.0003 (8) |
C8 | 0.0219 (11) | 0.0201 (12) | 0.0213 (10) | 0.0022 (8) | 0.0044 (8) | −0.0002 (8) |
C9 | 0.0176 (10) | 0.0208 (11) | 0.0226 (11) | −0.0010 (8) | 0.0040 (8) | −0.0008 (8) |
C10 | 0.0240 (11) | 0.0276 (12) | 0.0248 (12) | 0.0055 (10) | 0.0069 (9) | −0.0003 (9) |
C15 | 0.0213 (10) | 0.0210 (11) | 0.0137 (9) | −0.0039 (8) | 0.0013 (8) | −0.0003 (8) |
C16 | 0.0212 (10) | 0.0235 (12) | 0.0220 (10) | −0.0034 (9) | 0.0068 (8) | −0.0005 (8) |
C17 | 0.0246 (11) | 0.0204 (11) | 0.0257 (11) | −0.0047 (9) | 0.0073 (9) | 0.0020 (9) |
C18 | 0.0216 (10) | 0.0247 (12) | 0.0162 (9) | 0.0001 (9) | 0.0015 (8) | −0.0007 (8) |
C19 | 0.0198 (10) | 0.0243 (12) | 0.0196 (10) | −0.0061 (9) | 0.0046 (8) | −0.0007 (8) |
C20 | 0.0229 (11) | 0.0235 (12) | 0.0182 (10) | −0.0047 (9) | 0.0043 (8) | −0.0005 (8) |
C22 | 0.0180 (10) | 0.0339 (13) | 0.0273 (11) | 0.0008 (9) | 0.0028 (8) | 0.0009 (9) |
S12—O13 | 1.4282 (15) | C15—C20 | 1.390 (3) |
S12—O14 | 1.4256 (16) | C16—C17 | 1.370 (3) |
S12—N1 | 1.6875 (18) | C17—C18 | 1.398 (3) |
S12—C15 | 1.740 (2) | C18—C19 | 1.394 (3) |
O11—C10 | 1.219 (3) | C19—C20 | 1.389 (3) |
O21—C18 | 1.355 (3) | C3—H3 | 0.9300 |
O21—C22 | 1.435 (3) | C4—H4 | 0.9300 |
N1—C2 | 1.414 (3) | C5—H5 | 0.9300 |
N1—C9 | 1.389 (3) | C6—H6 | 0.9300 |
C2—C3 | 1.387 (3) | C9—H9 | 0.9300 |
C2—C7 | 1.405 (3) | C10—H10 | 0.9300 |
C3—C4 | 1.391 (3) | C16—H16 | 0.9300 |
C4—C5 | 1.396 (3) | C17—H17 | 0.9300 |
C5—C6 | 1.378 (3) | C19—H19 | 0.9300 |
C6—C7 | 1.402 (3) | C20—H20 | 0.9300 |
C7—C8 | 1.451 (3) | C22—H22A | 0.9600 |
C8—C9 | 1.366 (3) | C22—H22B | 0.9600 |
C8—C10 | 1.453 (3) | C22—H22C | 0.9600 |
C15—C16 | 1.401 (3) | ||
S12···H3 | 3.0800 | C6···H10ii | 2.8900 |
O11···C6 | 3.193 (3) | C7···H4vi | 3.0100 |
O11···C22i | 3.327 (3) | C7···H10ii | 2.8500 |
O11···C16ii | 3.170 (3) | C8···H4vi | 3.0500 |
O11···C17ii | 3.211 (3) | C10···H4vi | 3.0600 |
O13···C19iii | 3.309 (3) | C16···H22Aiii | 3.0000 |
O14···C3 | 3.095 (3) | C17···H22Civ | 3.0300 |
O21···C22iv | 3.391 (3) | C18···H6vi | 3.0300 |
O21···C3v | 3.345 (3) | C18···H22Civ | 3.0100 |
O11···H6 | 2.7100 | C19···H22A | 2.8800 |
O11···H22Ai | 2.4500 | C19···H22C | 2.6800 |
O11···H17ii | 2.7200 | C20···H20viii | 3.0300 |
O11···H16ii | 2.6400 | C22···H19 | 2.5500 |
O11···H4vi | 2.8400 | H3···S12 | 3.0800 |
O13···H9 | 2.6200 | H3···O14 | 2.5300 |
O13···H16 | 2.7000 | H3···O21vii | 2.5900 |
O13···H19iii | 2.6600 | H4···O11i | 2.8400 |
O14···H17vii | 2.7600 | H4···C6i | 3.0400 |
O14···H19viii | 2.8800 | H4···C7i | 3.0100 |
O14···H22Cviii | 2.6300 | H4···C8i | 3.0500 |
O14···H20 | 2.6100 | H4···C10i | 3.0600 |
O14···H3 | 2.5300 | H6···O11 | 2.7100 |
O21···H3v | 2.5900 | H6···C18i | 3.0300 |
O21···H22Civ | 2.8400 | H9···O13 | 2.6200 |
C2···C10ii | 3.494 (3) | H10···C5iii | 3.0200 |
C3···O14 | 3.095 (3) | H10···C2x | 3.0000 |
C3···O21vii | 3.345 (3) | H10···C5x | 3.0700 |
C4···C6i | 3.423 (4) | H10···C6x | 2.8900 |
C4···C7i | 3.485 (3) | H10···C7x | 2.8500 |
C5···C7i | 3.554 (3) | H16···O13 | 2.7000 |
C5···C10ix | 3.462 (3) | H16···H22Aiii | 2.3600 |
C6···O11 | 3.193 (3) | H16···O11x | 2.6400 |
C6···C4vi | 3.423 (4) | H17···O14v | 2.7600 |
C7···C5vi | 3.554 (3) | H17···O11x | 2.7200 |
C7···C4vi | 3.485 (3) | H19···O13ix | 2.6600 |
C7···C10ii | 3.348 (3) | H19···C22 | 2.5500 |
C10···C2x | 3.494 (3) | H19···H22A | 2.4700 |
C10···C5iii | 3.462 (3) | H19···H22C | 2.2400 |
C10···C7x | 3.348 (3) | H19···O14viii | 2.8800 |
C16···O11x | 3.170 (3) | H20···O14 | 2.6100 |
C17···O11x | 3.211 (3) | H20···C20viii | 3.0300 |
C17···C22iv | 3.560 (3) | H22A···C16ix | 3.0000 |
C18···C22iv | 3.402 (3) | H22A···C19 | 2.8800 |
C19···O13ix | 3.309 (3) | H22A···H16ix | 2.3600 |
C20···C20viii | 3.511 (3) | H22A···H19 | 2.4700 |
C22···O21iv | 3.391 (3) | H22A···O11vi | 2.4500 |
C22···C18iv | 3.402 (3) | H22C···C19 | 2.6800 |
C22···C17iv | 3.560 (3) | H22C···H19 | 2.2400 |
C22···O11vi | 3.327 (3) | H22C···O14viii | 2.6300 |
C2···H10ii | 3.0000 | H22C···O21iv | 2.8400 |
C5···H10ii | 3.0700 | H22C···C17iv | 3.0300 |
C5···H10ix | 3.0200 | H22C···C18iv | 3.0100 |
C6···H4vi | 3.0400 | ||
O13—S12—O14 | 121.04 (9) | O21—C18—C19 | 124.99 (19) |
O13—S12—N1 | 103.91 (8) | C17—C18—C19 | 120.2 (2) |
O13—S12—C15 | 110.15 (10) | C18—C19—C20 | 119.7 (2) |
O14—S12—N1 | 106.37 (9) | C15—C20—C19 | 119.8 (2) |
O14—S12—C15 | 109.96 (10) | C2—C3—H3 | 122.00 |
N1—S12—C15 | 103.77 (9) | C4—C3—H3 | 122.00 |
C18—O21—C22 | 118.58 (17) | C3—C4—H4 | 119.00 |
S12—N1—C2 | 125.72 (13) | C5—C4—H4 | 119.00 |
S12—N1—C9 | 123.61 (14) | C4—C5—H5 | 119.00 |
C2—N1—C9 | 108.54 (16) | C6—C5—H5 | 119.00 |
N1—C2—C3 | 129.85 (18) | C5—C6—H6 | 121.00 |
N1—C2—C7 | 107.24 (17) | C7—C6—H6 | 121.00 |
C3—C2—C7 | 122.90 (19) | N1—C9—H9 | 125.00 |
C2—C3—C4 | 116.6 (2) | C8—C9—H9 | 125.00 |
C3—C4—C5 | 121.4 (2) | O11—C10—H10 | 118.00 |
C4—C5—C6 | 121.7 (2) | C8—C10—H10 | 118.00 |
C5—C6—C7 | 118.1 (2) | C15—C16—H16 | 120.00 |
C2—C7—C6 | 119.3 (2) | C17—C16—H16 | 120.00 |
C2—C7—C8 | 107.10 (17) | C16—C17—H17 | 120.00 |
C6—C7—C8 | 133.61 (19) | C18—C17—H17 | 120.00 |
C7—C8—C9 | 107.51 (18) | C18—C19—H19 | 120.00 |
C7—C8—C10 | 127.88 (18) | C20—C19—H19 | 120.00 |
C9—C8—C10 | 124.6 (2) | C15—C20—H20 | 120.00 |
N1—C9—C8 | 109.60 (19) | C19—C20—H20 | 120.00 |
O11—C10—C8 | 123.3 (2) | O21—C22—H22A | 109.00 |
S12—C15—C16 | 118.52 (16) | O21—C22—H22B | 109.00 |
S12—C15—C20 | 121.20 (19) | O21—C22—H22C | 109.00 |
C16—C15—C20 | 120.3 (2) | H22A—C22—H22B | 110.00 |
C15—C16—C17 | 119.9 (2) | H22A—C22—H22C | 109.00 |
C16—C17—C18 | 120.1 (2) | H22B—C22—H22C | 109.00 |
O21—C18—C17 | 114.8 (2) | ||
O13—S12—N1—C2 | 175.17 (15) | C3—C2—C7—C8 | −179.4 (2) |
O14—S12—N1—C2 | 46.38 (17) | C2—C3—C4—C5 | −0.5 (3) |
C15—S12—N1—C2 | −69.61 (17) | C3—C4—C5—C6 | 0.3 (4) |
O13—S12—N1—C9 | −23.36 (19) | C4—C5—C6—C7 | −0.2 (4) |
O14—S12—N1—C9 | −152.15 (17) | C5—C6—C7—C8 | 178.9 (3) |
C15—S12—N1—C9 | 91.86 (18) | C5—C6—C7—C2 | 0.3 (3) |
N1—S12—C15—C20 | 103.34 (17) | C2—C7—C8—C10 | −180.0 (2) |
O14—S12—C15—C16 | 169.75 (15) | C6—C7—C8—C9 | −179.0 (3) |
N1—S12—C15—C16 | −76.82 (17) | C2—C7—C8—C9 | −0.3 (3) |
O13—S12—C15—C16 | 33.89 (19) | C6—C7—C8—C10 | 1.3 (5) |
O14—S12—C15—C20 | −10.1 (2) | C7—C8—C9—N1 | 0.9 (3) |
O13—S12—C15—C20 | −145.96 (16) | C10—C8—C9—N1 | −179.4 (2) |
C22—O21—C18—C17 | 179.34 (17) | C7—C8—C10—O11 | 6.8 (4) |
C22—O21—C18—C19 | −1.7 (3) | C9—C8—C10—O11 | −172.8 (2) |
C9—N1—C2—C3 | 179.9 (2) | S12—C15—C20—C19 | 177.73 (15) |
C2—N1—C9—C8 | −1.2 (2) | C16—C15—C20—C19 | −2.1 (3) |
C9—N1—C2—C7 | 1.0 (2) | S12—C15—C16—C17 | −178.04 (16) |
S12—N1—C2—C7 | 164.81 (15) | C20—C15—C16—C17 | 1.8 (3) |
S12—N1—C2—C3 | −16.3 (3) | C15—C16—C17—C18 | 0.3 (3) |
S12—N1—C9—C8 | −165.41 (16) | C16—C17—C18—C19 | −2.1 (3) |
N1—C2—C3—C4 | −178.2 (2) | C16—C17—C18—O21 | 176.95 (18) |
N1—C2—C7—C8 | −0.5 (2) | O21—C18—C19—C20 | −177.17 (18) |
C7—C2—C3—C4 | 0.6 (3) | C17—C18—C19—C20 | 1.8 (3) |
N1—C2—C7—C6 | 178.5 (2) | C18—C19—C20—C15 | 0.3 (3) |
C3—C2—C7—C6 | −0.5 (3) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+2, y−1/2, −z+1/2; (iii) x+1, y, z; (iv) −x+1, −y+2, −z+1; (v) x, y+1, z; (vi) −x+1, y+1/2, −z+1/2; (vii) x, y−1, z; (viii) −x+1, −y+1, −z+1; (ix) x−1, y, z; (x) −x+2, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O14 | 0.93 | 2.53 | 3.095 (3) | 119 |
C3—H3···O21vii | 0.93 | 2.59 | 3.345 (3) | 139 |
C22—H22A···O11vi | 0.96 | 2.45 | 3.327 (3) | 151 |
Symmetry codes: (vi) −x+1, y+1/2, −z+1/2; (vii) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O14 | 0.9300 | 2.5300 | 3.095 (3) | 119.00 |
C3—H3···O21i | 0.9300 | 2.5900 | 3.345 (3) | 139.00 |
C22—H22A···O11ii | 0.9600 | 2.4500 | 3.327 (3) | 151.00 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H13NO4S |
Mr | 315.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 6.9942 (7), 8.2942 (9), 24.598 (3) |
β (°) | 96.814 (2) |
V (Å3) | 1416.9 (3) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 2.20 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Bruker X8 Proteum |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10500, 2291, 2220 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.584 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.106, 1.10 |
No. of reflections | 2291 |
No. of parameters | 200 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.43 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
Acknowledgements
MM thanks UGC, New Delhi, Government of India, for the award of project No. 41-920/2012(SR) (dated: 25–07–2012). Also, KSV gratefully acknowledges UGC–BSR, New Delhi, for financial support.
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