Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040536/wn2193sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040536/wn2193Isup2.hkl |
CCDC reference: 660323
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C)= 0.002 Å
- R factor = 0.048
- wR factor = 0.119
- Data-to-parameter ratio = 27.4
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
(E)-Ethyl 3-[2-(hydroxymethyl)-1-(phenylsulfonyl)-1H-indol-3-yl)acrylate (1.3 mmol) and boron trifluoride etherate solution (5 drops) in dry benzene (20 ml) were refuxed for 4 h. After completion of the reaction, the mixture was poured into ice-water, washed with water (3 × 10 ml) followed by solvent removal to give the crude product. It was recrystallized from methanol (5 ml).
H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.95 Å (Csp2), 0.98 Å (methyl) and 0.99 Å (methylene), and Uiso(H) value of 1.2Ueq(C) or 1.5Ueq(Cmethyl)
The background to this study is set out in Senthil Kumar et al. (2006a,b,c,d). We now describe the X-ray crystal structure determination of the title compound.
Bond distances and angles in the title compound are comparable to those observed for ethyl 3-(2-methoxycarbonylmethyl-1-phenylsulfonyl-1H-indol-3-yl)acrylate (Senthil Kumar et al., 2006c). The indole ring system is planar with atom C5 deviating by a maximum of 0.027 (1) Å, from the mean plane through that ring system. As observed in other phenylsulfonylindoles (Senthil Kumar et al., 2006a,b,c,d), atom S1 has a distorted tetrahedral configuration, with angles O1—S1—O2 [120.60 (6)°] and N1—S1—C9 [104.87 (6)°] deviating significantly from ideal tetrahedral values. The conformation of the phenylsulfonyl group with respect to the indole unit is described by the torsion angles O1—S1—N1—C1 = 22.55 (12)°, O2—S1—N1—C8 = -36.63 (11)° and N1—S1—C9—C10 = 98.91 (11)°. This conformation is influenced by the intramolecular C—H···O interactions, C7—H7···O2 and C15—H15A···O1, involving the sulfonyl O1 and O2 atoms which deviate 0.143 (1) and 0.509 (1) Å, respectively, from the plane of the indole ring system.
The dihedral angle between the C9—C14 phenyl ring and indole ring system is 81.39 (4)°. The torsion angle N1—C1—C15—C16 of 81.74 (15)° describes the conformation of the attachment of the benzyl substituent to the indole ring system and torsion angle C1—C15—C16—C21 of 24.17 (18)° shows how the C16—C21 phenyl ring is oriented. This conformation is influenced by the intramolecular C15—H15A···O1 interaction, and by the C—H···π interaction involving H10 and the C16—C21 ring, with H10 separated from the ring centroid (Cg1) by 2.75 Å (Table 1). The dihedral angle between the mean planes through the C9—C14 and C16—C21 aromatic rings is 33.35 (6)°; the centroids of these two rings are separated by 4.4737 (8) Å and hence there is no π-π interaction between them.
Atoms O3, O4, C22 to C26 of the ethyl acrylate substituent group at C2 are coplanar (r.m.s deviation of 0.054 Å). This plane is slightly twisted away from the indole ring system by an angle of 7.91 (4)°.
The C18—H18···O3 hydrogen bonds link the inversion-related molecules at (x, y, z) and (-x, 1 - y, -z) into a centrosymmetric dimer. The dimer structure is further stabilized by a weak π-π stacking interaction between the phenyl rings (C16—C21) of the benzyl groups; the centroid–centroid distance between the rings is 3.8027 (9) Å and the perpendicular distance is 3.743 Å. The dimers are linked through C—H···π interactions (Table 1) involving H11 and the benzene ring (C3—C8; centroid Cg2) of the indole ring system, to form a two-dimensional network parallel to the bc plane (Fig. 2).
For general background and related structures, see: Senthil Kumar et al. (2006a,b,c,d).
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL (Sheldrick, 1998); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).
C26H23NO4S | F(000) = 936 |
Mr = 445.51 | Dx = 1.367 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7382 reflections |
a = 11.4683 (2) Å | θ = 2.4–30.6° |
b = 8.8983 (1) Å | µ = 0.18 mm−1 |
c = 21.5088 (3) Å | T = 100 K |
β = 99.406 (1)° | Block, yellow |
V = 2165.43 (5) Å3 | 0.28 × 0.25 × 0.24 mm |
Z = 4 |
Bruker SMART APEX2 CCD area-detector diffractometer | 7943 independent reflections |
Radiation source: fine-focus sealed tube | 5869 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
Detector resolution: 8.33 pixels mm-1 | θmax = 32.7°, θmin = 1.9° |
ω scans | h = −17→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −12→13 |
Tmin = 0.912, Tmax = 0.958 | l = −32→31 |
47728 measured 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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0462P)2 + 0.737P] where P = (Fo2 + 2Fc2)/3 |
7943 reflections | (Δ/σ)max = 0.001 |
290 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.54 e Å−3 |
C26H23NO4S | V = 2165.43 (5) Å3 |
Mr = 445.51 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.4683 (2) Å | µ = 0.18 mm−1 |
b = 8.8983 (1) Å | T = 100 K |
c = 21.5088 (3) Å | 0.28 × 0.25 × 0.24 mm |
β = 99.406 (1)° |
Bruker SMART APEX2 CCD area-detector diffractometer | 7943 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 5869 reflections with I > 2σ(I) |
Tmin = 0.912, Tmax = 0.958 | Rint = 0.060 |
47728 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.41 e Å−3 |
7943 reflections | Δρmin = −0.54 e Å−3 |
290 parameters |
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.27475 (3) | 0.34607 (4) | 0.252973 (15) | 0.01888 (8) | |
O1 | 0.26409 (9) | 0.23974 (11) | 0.20278 (5) | 0.0246 (2) | |
O2 | 0.35867 (8) | 0.32365 (11) | 0.30905 (5) | 0.0235 (2) | |
O3 | 0.29725 (11) | 0.91913 (13) | −0.02392 (5) | 0.0337 (3) | |
O4 | 0.37486 (9) | 1.13030 (11) | 0.02295 (4) | 0.0255 (2) | |
N1 | 0.31080 (9) | 0.51204 (12) | 0.22307 (5) | 0.0177 (2) | |
C1 | 0.29109 (11) | 0.55791 (14) | 0.15938 (6) | 0.0173 (2) | |
C2 | 0.32209 (11) | 0.70722 (14) | 0.15648 (6) | 0.0168 (2) | |
C3 | 0.36031 (10) | 0.75975 (14) | 0.22039 (6) | 0.0164 (2) | |
C4 | 0.39607 (11) | 0.90026 (15) | 0.24600 (6) | 0.0181 (2) | |
H4 | 0.4010 | 0.9843 | 0.2193 | 0.022* | |
C5 | 0.42414 (12) | 0.91474 (16) | 0.31074 (6) | 0.0214 (3) | |
H5 | 0.4468 | 1.0101 | 0.3286 | 0.026* | |
C6 | 0.41952 (12) | 0.79078 (16) | 0.35020 (6) | 0.0223 (3) | |
H6 | 0.4410 | 0.8029 | 0.3945 | 0.027* | |
C7 | 0.38426 (11) | 0.65075 (15) | 0.32612 (6) | 0.0203 (2) | |
H7 | 0.3812 | 0.5667 | 0.3530 | 0.024* | |
C8 | 0.35341 (11) | 0.63749 (14) | 0.26097 (6) | 0.0169 (2) | |
C9 | 0.13509 (11) | 0.37614 (14) | 0.27434 (6) | 0.0190 (2) | |
C10 | 0.03426 (12) | 0.32885 (16) | 0.23390 (6) | 0.0231 (3) | |
H10 | 0.0407 | 0.2792 | 0.1955 | 0.028* | |
C11 | −0.07581 (12) | 0.35557 (17) | 0.25069 (7) | 0.0261 (3) | |
H11 | −0.1455 | 0.3244 | 0.2236 | 0.031* | |
C12 | −0.08422 (12) | 0.42756 (16) | 0.30685 (7) | 0.0253 (3) | |
H12 | −0.1598 | 0.4472 | 0.3177 | 0.030* | |
C13 | 0.01697 (12) | 0.47128 (16) | 0.34750 (7) | 0.0250 (3) | |
H13 | 0.0102 | 0.5183 | 0.3864 | 0.030* | |
C14 | 0.12761 (12) | 0.44652 (15) | 0.33152 (6) | 0.0221 (3) | |
H14 | 0.1971 | 0.4769 | 0.3590 | 0.027* | |
C15 | 0.24417 (12) | 0.45820 (15) | 0.10488 (6) | 0.0206 (3) | |
H15A | 0.2807 | 0.3576 | 0.1124 | 0.025* | |
H15B | 0.2691 | 0.4996 | 0.0664 | 0.025* | |
C16 | 0.11042 (12) | 0.43986 (15) | 0.09285 (6) | 0.0206 (3) | |
C17 | 0.06111 (14) | 0.31429 (17) | 0.06005 (7) | 0.0265 (3) | |
H17 | 0.1112 | 0.2417 | 0.0456 | 0.032* | |
C18 | −0.06059 (14) | 0.29404 (18) | 0.04830 (7) | 0.0319 (3) | |
H18 | −0.0932 | 0.2079 | 0.0258 | 0.038* | |
C19 | −0.13458 (14) | 0.39880 (19) | 0.06916 (7) | 0.0317 (3) | |
H19 | −0.2177 | 0.3838 | 0.0617 | 0.038* | |
C20 | −0.08669 (13) | 0.52580 (19) | 0.10099 (7) | 0.0305 (3) | |
H20 | −0.1371 | 0.5985 | 0.1151 | 0.037* | |
C21 | 0.03539 (13) | 0.54664 (16) | 0.11225 (7) | 0.0253 (3) | |
H21 | 0.0677 | 0.6347 | 0.1334 | 0.030* | |
C22 | 0.31486 (11) | 0.78830 (15) | 0.09784 (6) | 0.0190 (2) | |
H22 | 0.2829 | 0.7339 | 0.0610 | 0.023* | |
C23 | 0.34727 (12) | 0.93034 (15) | 0.08850 (6) | 0.0213 (3) | |
H23 | 0.3773 | 0.9928 | 0.1233 | 0.026* | |
C24 | 0.33564 (12) | 0.98804 (15) | 0.02363 (6) | 0.0208 (3) | |
C25 | 0.36841 (14) | 1.19570 (17) | −0.03932 (6) | 0.0275 (3) | |
H25A | 0.2849 | 1.2104 | −0.0590 | 0.033* | |
H25B | 0.4067 | 1.1286 | −0.0667 | 0.033* | |
C26 | 0.43137 (16) | 1.34387 (17) | −0.03127 (7) | 0.0312 (3) | |
H26A | 0.4278 | 1.3922 | −0.0725 | 0.047* | |
H26B | 0.5141 | 1.3276 | −0.0124 | 0.047* | |
H26C | 0.3933 | 1.4087 | −0.0037 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02132 (15) | 0.01453 (14) | 0.02155 (15) | 0.00192 (11) | 0.00570 (12) | 0.00244 (11) |
O1 | 0.0317 (5) | 0.0159 (4) | 0.0278 (5) | 0.0009 (4) | 0.0100 (4) | −0.0008 (4) |
O2 | 0.0225 (5) | 0.0228 (5) | 0.0251 (5) | 0.0049 (4) | 0.0039 (4) | 0.0079 (4) |
O3 | 0.0488 (7) | 0.0312 (6) | 0.0189 (5) | −0.0167 (5) | −0.0013 (4) | 0.0008 (4) |
O4 | 0.0393 (6) | 0.0207 (5) | 0.0161 (4) | −0.0072 (4) | 0.0032 (4) | 0.0031 (4) |
N1 | 0.0201 (5) | 0.0155 (5) | 0.0175 (5) | −0.0005 (4) | 0.0036 (4) | 0.0012 (4) |
C1 | 0.0178 (5) | 0.0181 (6) | 0.0166 (5) | 0.0000 (4) | 0.0044 (4) | −0.0004 (4) |
C2 | 0.0165 (5) | 0.0170 (5) | 0.0171 (5) | −0.0005 (4) | 0.0032 (4) | 0.0004 (4) |
C3 | 0.0144 (5) | 0.0178 (5) | 0.0170 (5) | 0.0007 (4) | 0.0025 (4) | 0.0004 (4) |
C4 | 0.0178 (5) | 0.0178 (6) | 0.0189 (6) | −0.0006 (4) | 0.0034 (4) | −0.0006 (5) |
C5 | 0.0213 (6) | 0.0222 (6) | 0.0200 (6) | −0.0027 (5) | 0.0020 (5) | −0.0031 (5) |
C6 | 0.0224 (6) | 0.0272 (7) | 0.0163 (6) | −0.0009 (5) | 0.0000 (5) | −0.0008 (5) |
C7 | 0.0203 (6) | 0.0227 (6) | 0.0174 (6) | 0.0008 (5) | 0.0012 (5) | 0.0032 (5) |
C8 | 0.0150 (5) | 0.0169 (6) | 0.0189 (6) | 0.0007 (4) | 0.0030 (4) | 0.0003 (4) |
C9 | 0.0199 (6) | 0.0171 (6) | 0.0209 (6) | −0.0002 (4) | 0.0055 (5) | 0.0033 (5) |
C10 | 0.0255 (6) | 0.0238 (6) | 0.0201 (6) | −0.0054 (5) | 0.0044 (5) | 0.0004 (5) |
C11 | 0.0211 (6) | 0.0310 (7) | 0.0258 (7) | −0.0063 (5) | 0.0025 (5) | 0.0024 (6) |
C12 | 0.0219 (6) | 0.0227 (6) | 0.0324 (7) | −0.0008 (5) | 0.0075 (5) | 0.0036 (6) |
C13 | 0.0255 (7) | 0.0231 (6) | 0.0278 (7) | −0.0008 (5) | 0.0087 (5) | −0.0037 (5) |
C14 | 0.0218 (6) | 0.0219 (6) | 0.0226 (6) | −0.0013 (5) | 0.0033 (5) | −0.0015 (5) |
C15 | 0.0258 (6) | 0.0176 (6) | 0.0186 (6) | −0.0026 (5) | 0.0047 (5) | −0.0025 (5) |
C16 | 0.0242 (6) | 0.0197 (6) | 0.0173 (6) | −0.0038 (5) | 0.0015 (5) | 0.0015 (5) |
C17 | 0.0327 (7) | 0.0235 (7) | 0.0222 (6) | −0.0042 (6) | 0.0006 (5) | −0.0026 (5) |
C18 | 0.0353 (8) | 0.0285 (7) | 0.0284 (7) | −0.0109 (6) | −0.0052 (6) | 0.0019 (6) |
C19 | 0.0244 (7) | 0.0380 (8) | 0.0299 (8) | −0.0064 (6) | −0.0037 (6) | 0.0095 (7) |
C20 | 0.0252 (7) | 0.0334 (8) | 0.0317 (8) | 0.0019 (6) | 0.0009 (6) | 0.0039 (6) |
C21 | 0.0256 (7) | 0.0227 (7) | 0.0269 (7) | −0.0018 (5) | 0.0017 (5) | −0.0013 (5) |
C22 | 0.0194 (6) | 0.0205 (6) | 0.0170 (5) | −0.0018 (5) | 0.0025 (4) | 0.0001 (5) |
C23 | 0.0261 (6) | 0.0214 (6) | 0.0157 (6) | −0.0035 (5) | 0.0013 (5) | 0.0005 (5) |
C24 | 0.0221 (6) | 0.0219 (6) | 0.0180 (6) | −0.0032 (5) | 0.0024 (5) | 0.0019 (5) |
C25 | 0.0378 (8) | 0.0271 (7) | 0.0171 (6) | −0.0044 (6) | 0.0030 (5) | 0.0067 (5) |
C26 | 0.0492 (9) | 0.0227 (7) | 0.0239 (7) | −0.0045 (6) | 0.0121 (7) | 0.0036 (6) |
S1—O1 | 1.4257 (10) | C12—C13 | 1.389 (2) |
S1—O2 | 1.4288 (10) | C12—H12 | 0.95 |
S1—N1 | 1.6889 (11) | C13—C14 | 1.3853 (19) |
S1—C9 | 1.7574 (13) | C13—H13 | 0.95 |
O3—C24 | 1.2118 (16) | C14—H14 | 0.95 |
O4—C24 | 1.3443 (16) | C15—C16 | 1.5220 (19) |
O4—C25 | 1.4510 (16) | C15—H15A | 0.99 |
N1—C1 | 1.4118 (16) | C15—H15B | 0.99 |
N1—C8 | 1.4210 (16) | C16—C21 | 1.391 (2) |
C1—C2 | 1.3794 (18) | C16—C17 | 1.3913 (19) |
C1—C15 | 1.4984 (17) | C17—C18 | 1.389 (2) |
C2—C22 | 1.4436 (18) | C17—H17 | 0.95 |
C2—C3 | 1.4503 (17) | C18—C19 | 1.384 (2) |
C3—C4 | 1.4004 (18) | C18—H18 | 0.95 |
C3—C8 | 1.4051 (17) | C19—C20 | 1.387 (2) |
C4—C5 | 1.3830 (18) | C19—H19 | 0.95 |
C4—H4 | 0.95 | C20—C21 | 1.394 (2) |
C5—C6 | 1.3980 (19) | C20—H20 | 0.95 |
C5—H5 | 0.95 | C21—H21 | 0.95 |
C6—C7 | 1.3842 (19) | C22—C23 | 1.3418 (18) |
C6—H6 | 0.95 | C22—H22 | 0.95 |
C7—C8 | 1.3930 (18) | C23—C24 | 1.4722 (18) |
C7—H7 | 0.95 | C23—H23 | 0.95 |
C9—C10 | 1.3935 (19) | C25—C26 | 1.500 (2) |
C9—C14 | 1.3954 (19) | C25—H25A | 0.99 |
C10—C11 | 1.389 (2) | C25—H25B | 0.99 |
C10—H10 | 0.95 | C26—H26A | 0.98 |
C11—C12 | 1.384 (2) | C26—H26B | 0.98 |
C11—H11 | 0.95 | C26—H26C | 0.98 |
O1—S1—O2 | 120.60 (6) | C13—C14—C9 | 118.74 (12) |
O1—S1—N1 | 106.74 (6) | C13—C14—H14 | 120.6 |
O2—S1—N1 | 105.69 (6) | C9—C14—H14 | 120.6 |
O1—S1—C9 | 109.27 (6) | C1—C15—C16 | 114.81 (11) |
O2—S1—C9 | 108.51 (6) | C1—C15—H15A | 108.6 |
N1—S1—C9 | 104.87 (6) | C16—C15—H15A | 108.6 |
C24—O4—C25 | 114.90 (11) | C1—C15—H15B | 108.6 |
C1—N1—C8 | 108.36 (10) | C16—C15—H15B | 108.6 |
C1—N1—S1 | 127.73 (9) | H15A—C15—H15B | 107.5 |
C8—N1—S1 | 123.44 (9) | C21—C16—C17 | 118.73 (13) |
C2—C1—N1 | 108.71 (11) | C21—C16—C15 | 122.10 (12) |
C2—C1—C15 | 126.67 (11) | C17—C16—C15 | 119.15 (12) |
N1—C1—C15 | 124.62 (11) | C18—C17—C16 | 120.63 (15) |
C1—C2—C22 | 122.85 (12) | C18—C17—H17 | 119.7 |
C1—C2—C3 | 107.92 (11) | C16—C17—H17 | 119.7 |
C22—C2—C3 | 129.23 (12) | C19—C18—C17 | 120.32 (14) |
C4—C3—C8 | 119.31 (11) | C19—C18—H18 | 119.8 |
C4—C3—C2 | 133.18 (12) | C17—C18—H18 | 119.8 |
C8—C3—C2 | 107.48 (11) | C18—C19—C20 | 119.64 (14) |
C5—C4—C3 | 118.96 (12) | C18—C19—H19 | 120.2 |
C5—C4—H4 | 120.5 | C20—C19—H19 | 120.2 |
C3—C4—H4 | 120.5 | C19—C20—C21 | 119.97 (15) |
C4—C5—C6 | 120.81 (12) | C19—C20—H20 | 120.0 |
C4—C5—H5 | 119.6 | C21—C20—H20 | 120.0 |
C6—C5—H5 | 119.6 | C16—C21—C20 | 120.67 (14) |
C7—C6—C5 | 121.38 (12) | C16—C21—H21 | 119.7 |
C7—C6—H6 | 119.3 | C20—C21—H21 | 119.7 |
C5—C6—H6 | 119.3 | C23—C22—C2 | 128.59 (12) |
C6—C7—C8 | 117.60 (12) | C23—C22—H22 | 115.7 |
C6—C7—H7 | 121.2 | C2—C22—H22 | 115.7 |
C8—C7—H7 | 121.2 | C22—C23—C24 | 119.08 (12) |
C7—C8—C3 | 121.90 (12) | C22—C23—H23 | 120.5 |
C7—C8—N1 | 130.59 (12) | C24—C23—H23 | 120.5 |
C3—C8—N1 | 107.51 (11) | O3—C24—O4 | 122.91 (12) |
C10—C9—C14 | 121.43 (12) | O3—C24—C23 | 125.98 (13) |
C10—C9—S1 | 119.31 (10) | O4—C24—C23 | 111.10 (11) |
C14—C9—S1 | 119.26 (10) | O4—C25—C26 | 107.16 (12) |
C11—C10—C9 | 118.86 (13) | O4—C25—H25A | 110.3 |
C11—C10—H10 | 120.6 | C26—C25—H25A | 110.3 |
C9—C10—H10 | 120.6 | O4—C25—H25B | 110.3 |
C12—C11—C10 | 120.13 (13) | C26—C25—H25B | 110.3 |
C12—C11—H11 | 119.9 | H25A—C25—H25B | 108.5 |
C10—C11—H11 | 119.9 | C25—C26—H26A | 109.5 |
C11—C12—C13 | 120.56 (13) | C25—C26—H26B | 109.5 |
C11—C12—H12 | 119.7 | H26A—C26—H26B | 109.5 |
C13—C12—H12 | 119.7 | C25—C26—H26C | 109.5 |
C14—C13—C12 | 120.27 (13) | H26A—C26—H26C | 109.5 |
C14—C13—H13 | 119.9 | H26B—C26—H26C | 109.5 |
C12—C13—H13 | 119.9 | ||
O1—S1—N1—C1 | 22.55 (12) | O2—S1—C9—C10 | −148.51 (11) |
O2—S1—N1—C1 | 152.10 (11) | N1—S1—C9—C10 | 98.91 (11) |
C9—S1—N1—C1 | −93.33 (11) | O1—S1—C9—C14 | 164.62 (10) |
O1—S1—N1—C8 | −166.17 (10) | O2—S1—C9—C14 | 31.32 (12) |
O2—S1—N1—C8 | −36.63 (11) | N1—S1—C9—C14 | −81.26 (11) |
C9—S1—N1—C8 | 77.95 (11) | C14—C9—C10—C11 | 1.3 (2) |
C8—N1—C1—C2 | 1.03 (14) | S1—C9—C10—C11 | −178.86 (11) |
S1—N1—C1—C2 | 173.37 (9) | C9—C10—C11—C12 | −0.2 (2) |
C8—N1—C1—C15 | −178.99 (11) | C10—C11—C12—C13 | −1.2 (2) |
S1—N1—C1—C15 | −6.66 (18) | C11—C12—C13—C14 | 1.6 (2) |
N1—C1—C2—C22 | 178.70 (11) | C12—C13—C14—C9 | −0.5 (2) |
C15—C1—C2—C22 | −1.3 (2) | C10—C9—C14—C13 | −1.0 (2) |
N1—C1—C2—C3 | −1.33 (14) | S1—C9—C14—C13 | 179.21 (11) |
C15—C1—C2—C3 | 178.70 (12) | C2—C1—C15—C16 | −98.29 (15) |
C1—C2—C3—C4 | −176.70 (13) | N1—C1—C15—C16 | 81.74 (15) |
C22—C2—C3—C4 | 3.3 (2) | C1—C15—C16—C21 | 24.17 (18) |
C1—C2—C3—C8 | 1.14 (14) | C1—C15—C16—C17 | −157.46 (12) |
C22—C2—C3—C8 | −178.89 (12) | C21—C16—C17—C18 | −1.6 (2) |
C8—C3—C4—C5 | 0.24 (18) | C15—C16—C17—C18 | 179.96 (13) |
C2—C3—C4—C5 | 177.87 (13) | C16—C17—C18—C19 | 0.0 (2) |
C3—C4—C5—C6 | 1.37 (19) | C17—C18—C19—C20 | 1.1 (2) |
C4—C5—C6—C7 | −1.5 (2) | C18—C19—C20—C21 | −0.5 (2) |
C5—C6—C7—C8 | 0.0 (2) | C17—C16—C21—C20 | 2.2 (2) |
C6—C7—C8—C3 | 1.65 (19) | C15—C16—C21—C20 | −179.43 (13) |
C6—C7—C8—N1 | −177.70 (12) | C19—C20—C21—C16 | −1.1 (2) |
C4—C3—C8—C7 | −1.79 (18) | C1—C2—C22—C23 | −176.57 (13) |
C2—C3—C8—C7 | −179.98 (11) | C3—C2—C22—C23 | 3.5 (2) |
C4—C3—C8—N1 | 177.69 (11) | C2—C22—C23—C24 | 177.74 (13) |
C2—C3—C8—N1 | −0.50 (13) | C25—O4—C24—O3 | −0.3 (2) |
C1—N1—C8—C7 | 179.12 (13) | C25—O4—C24—C23 | 179.10 (12) |
S1—N1—C8—C7 | 6.38 (19) | C22—C23—C24—O3 | 1.0 (2) |
C1—N1—C8—C3 | −0.31 (13) | C22—C23—C24—O4 | −178.39 (12) |
S1—N1—C8—C3 | −173.04 (8) | C24—O4—C25—C26 | −171.93 (13) |
O1—S1—C9—C10 | −15.21 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O2 | 0.95 | 2.36 | 2.9424 (17) | 119 |
C15—H15A···O1 | 0.99 | 2.24 | 2.8474 (17) | 118 |
C18—H18···O3i | 0.95 | 2.59 | 3.282 (2) | 130 |
C10—H10···Cg1 | 0.95 | 2.75 | 3.3524 (14) | 122 |
C11—H11···Cg2ii | 0.95 | 2.81 | 3.6263 (15) | 145 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C26H23NO4S |
Mr | 445.51 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 11.4683 (2), 8.8983 (1), 21.5088 (3) |
β (°) | 99.406 (1) |
V (Å3) | 2165.43 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.28 × 0.25 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART APEX2 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.912, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 47728, 7943, 5869 |
Rint | 0.060 |
(sin θ/λ)max (Å−1) | 0.760 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.119, 1.06 |
No. of reflections | 7943 |
No. of parameters | 290 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.54 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O2 | 0.95 | 2.36 | 2.9424 (17) | 119 |
C15—H15A···O1 | 0.99 | 2.24 | 2.8474 (17) | 118 |
C18—H18···O3i | 0.95 | 2.59 | 3.282 (2) | 130 |
C10—H10···Cg1 | 0.95 | 2.75 | 3.3524 (14) | 122 |
C11—H11···Cg2ii | 0.95 | 2.81 | 3.6263 (15) | 145 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, y−1/2, −z+1/2. |
The background to this study is set out in Senthil Kumar et al. (2006a,b,c,d). We now describe the X-ray crystal structure determination of the title compound.
Bond distances and angles in the title compound are comparable to those observed for ethyl 3-(2-methoxycarbonylmethyl-1-phenylsulfonyl-1H-indol-3-yl)acrylate (Senthil Kumar et al., 2006c). The indole ring system is planar with atom C5 deviating by a maximum of 0.027 (1) Å, from the mean plane through that ring system. As observed in other phenylsulfonylindoles (Senthil Kumar et al., 2006a,b,c,d), atom S1 has a distorted tetrahedral configuration, with angles O1—S1—O2 [120.60 (6)°] and N1—S1—C9 [104.87 (6)°] deviating significantly from ideal tetrahedral values. The conformation of the phenylsulfonyl group with respect to the indole unit is described by the torsion angles O1—S1—N1—C1 = 22.55 (12)°, O2—S1—N1—C8 = -36.63 (11)° and N1—S1—C9—C10 = 98.91 (11)°. This conformation is influenced by the intramolecular C—H···O interactions, C7—H7···O2 and C15—H15A···O1, involving the sulfonyl O1 and O2 atoms which deviate 0.143 (1) and 0.509 (1) Å, respectively, from the plane of the indole ring system.
The dihedral angle between the C9—C14 phenyl ring and indole ring system is 81.39 (4)°. The torsion angle N1—C1—C15—C16 of 81.74 (15)° describes the conformation of the attachment of the benzyl substituent to the indole ring system and torsion angle C1—C15—C16—C21 of 24.17 (18)° shows how the C16—C21 phenyl ring is oriented. This conformation is influenced by the intramolecular C15—H15A···O1 interaction, and by the C—H···π interaction involving H10 and the C16—C21 ring, with H10 separated from the ring centroid (Cg1) by 2.75 Å (Table 1). The dihedral angle between the mean planes through the C9—C14 and C16—C21 aromatic rings is 33.35 (6)°; the centroids of these two rings are separated by 4.4737 (8) Å and hence there is no π-π interaction between them.
Atoms O3, O4, C22 to C26 of the ethyl acrylate substituent group at C2 are coplanar (r.m.s deviation of 0.054 Å). This plane is slightly twisted away from the indole ring system by an angle of 7.91 (4)°.
The C18—H18···O3 hydrogen bonds link the inversion-related molecules at (x, y, z) and (-x, 1 - y, -z) into a centrosymmetric dimer. The dimer structure is further stabilized by a weak π-π stacking interaction between the phenyl rings (C16—C21) of the benzyl groups; the centroid–centroid distance between the rings is 3.8027 (9) Å and the perpendicular distance is 3.743 Å. The dimers are linked through C—H···π interactions (Table 1) involving H11 and the benzene ring (C3—C8; centroid Cg2) of the indole ring system, to form a two-dimensional network parallel to the bc plane (Fig. 2).