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In the title compound, C26H23NO4S, the planes of the ethyl acrylate group, the sulfonyl-bound phenyl ring and the benzyl phenyl group are inclined at angles of 7.91 (4), 81.39 (4) and 88.33 (4)°, respectively, with respect to the indole ring system. The conformations of the phenyl­sulfonyl and benzyl substituents with respect to the indole ring system are influenced by intra­molecular C—H...O and C—H...π inter­actions. Inversion-related mol­ecules at (x, y, z) and (−x, 1 − y, −z) are linked into a centrosymmetric dimer by C—H...O hydrogen bonds. The dimers are crosslinked through C—H...π inter­actions, forming a two-dimensional network parallel to the bc plane. Weak π–π stacking inter­actions are present between the phenyl rings of the benzyl groups; the centroid-to-centroid distance between the rings is 3.8027 (9) Å and the perpendicular distance is 3.743 Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040536/wn2193sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040536/wn2193Isup2.hkl
Contains datablock I

CCDC reference: 660323

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.048
  • wR factor = 0.119
  • Data-to-parameter ratio = 27.4

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Comment top

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).

Related literature top

For general background and related structures, see: Senthil Kumar et al. (2006a,b,c,d).

Experimental top

(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).

Refinement top

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)

Structure description top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atomic numbering and 50% probability displacement ellipsoids. C—H···O hydrogen bonds are shown as dashed lines and the dotted line represents a C—H···π interaction.
[Figure 2] Fig. 2. Part of the crystal packing of the title compound, viewed approximately down the b axis. C—H···O hydrogen bonds are shown as dashed lines, C—H···π interactions are shown as double dashed lines and ππ interactions are shown as dotted lines. H atoms not involved in these interactions have been omitted.
Ethyl 3-[2-benzyl-1-(phenylsulfonyl)-1H-indol-3-yl]acrylate top
Crystal data top
C26H23NO4SF(000) = 936
Mr = 445.51Dx = 1.367 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7382 reflections
a = 11.4683 (2) Åθ = 2.4–30.6°
b = 8.8983 (1) ŵ = 0.18 mm1
c = 21.5088 (3) ÅT = 100 K
β = 99.406 (1)°Block, yellow
V = 2165.43 (5) Å30.28 × 0.25 × 0.24 mm
Z = 4
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
7943 independent reflections
Radiation source: fine-focus sealed tube5869 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
Detector resolution: 8.33 pixels mm-1θmax = 32.7°, θmin = 1.9°
ω scansh = 1714
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1213
Tmin = 0.912, Tmax = 0.958l = 3231
47728 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-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 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.54 e Å3
Crystal data top
C26H23NO4SV = 2165.43 (5) Å3
Mr = 445.51Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.4683 (2) ŵ = 0.18 mm1
b = 8.8983 (1) ÅT = 100 K
c = 21.5088 (3) Å0.28 × 0.25 × 0.24 mm
β = 99.406 (1)°
Data collection top
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 = 0.958Rint = 0.060
47728 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.06Δρmax = 0.41 e Å3
7943 reflectionsΔρmin = 0.54 e Å3
290 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.27475 (3)0.34607 (4)0.252973 (15)0.01888 (8)
O10.26409 (9)0.23974 (11)0.20278 (5)0.0246 (2)
O20.35867 (8)0.32365 (11)0.30905 (5)0.0235 (2)
O30.29725 (11)0.91913 (13)0.02392 (5)0.0337 (3)
O40.37486 (9)1.13030 (11)0.02295 (4)0.0255 (2)
N10.31080 (9)0.51204 (12)0.22307 (5)0.0177 (2)
C10.29109 (11)0.55791 (14)0.15938 (6)0.0173 (2)
C20.32209 (11)0.70722 (14)0.15648 (6)0.0168 (2)
C30.36031 (10)0.75975 (14)0.22039 (6)0.0164 (2)
C40.39607 (11)0.90026 (15)0.24600 (6)0.0181 (2)
H40.40100.98430.21930.022*
C50.42414 (12)0.91474 (16)0.31074 (6)0.0214 (3)
H50.44681.01010.32860.026*
C60.41952 (12)0.79078 (16)0.35020 (6)0.0223 (3)
H60.44100.80290.39450.027*
C70.38426 (11)0.65075 (15)0.32612 (6)0.0203 (2)
H70.38120.56670.35300.024*
C80.35341 (11)0.63749 (14)0.26097 (6)0.0169 (2)
C90.13509 (11)0.37614 (14)0.27434 (6)0.0190 (2)
C100.03426 (12)0.32885 (16)0.23390 (6)0.0231 (3)
H100.04070.27920.19550.028*
C110.07581 (12)0.35557 (17)0.25069 (7)0.0261 (3)
H110.14550.32440.22360.031*
C120.08422 (12)0.42756 (16)0.30685 (7)0.0253 (3)
H120.15980.44720.31770.030*
C130.01697 (12)0.47128 (16)0.34750 (7)0.0250 (3)
H130.01020.51830.38640.030*
C140.12761 (12)0.44652 (15)0.33152 (6)0.0221 (3)
H140.19710.47690.35900.027*
C150.24417 (12)0.45820 (15)0.10488 (6)0.0206 (3)
H15A0.28070.35760.11240.025*
H15B0.26910.49960.06640.025*
C160.11042 (12)0.43986 (15)0.09285 (6)0.0206 (3)
C170.06111 (14)0.31429 (17)0.06005 (7)0.0265 (3)
H170.11120.24170.04560.032*
C180.06059 (14)0.29404 (18)0.04830 (7)0.0319 (3)
H180.09320.20790.02580.038*
C190.13458 (14)0.39880 (19)0.06916 (7)0.0317 (3)
H190.21770.38380.06170.038*
C200.08669 (13)0.52580 (19)0.10099 (7)0.0305 (3)
H200.13710.59850.11510.037*
C210.03539 (13)0.54664 (16)0.11225 (7)0.0253 (3)
H210.06770.63470.13340.030*
C220.31486 (11)0.78830 (15)0.09784 (6)0.0190 (2)
H220.28290.73390.06100.023*
C230.34727 (12)0.93034 (15)0.08850 (6)0.0213 (3)
H230.37730.99280.12330.026*
C240.33564 (12)0.98804 (15)0.02363 (6)0.0208 (3)
C250.36841 (14)1.19570 (17)0.03932 (6)0.0275 (3)
H25A0.28491.21040.05900.033*
H25B0.40671.12860.06670.033*
C260.43137 (16)1.34387 (17)0.03127 (7)0.0312 (3)
H26A0.42781.39220.07250.047*
H26B0.51411.32760.01240.047*
H26C0.39331.40870.00370.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02132 (15)0.01453 (14)0.02155 (15)0.00192 (11)0.00570 (12)0.00244 (11)
O10.0317 (5)0.0159 (4)0.0278 (5)0.0009 (4)0.0100 (4)0.0008 (4)
O20.0225 (5)0.0228 (5)0.0251 (5)0.0049 (4)0.0039 (4)0.0079 (4)
O30.0488 (7)0.0312 (6)0.0189 (5)0.0167 (5)0.0013 (4)0.0008 (4)
O40.0393 (6)0.0207 (5)0.0161 (4)0.0072 (4)0.0032 (4)0.0031 (4)
N10.0201 (5)0.0155 (5)0.0175 (5)0.0005 (4)0.0036 (4)0.0012 (4)
C10.0178 (5)0.0181 (6)0.0166 (5)0.0000 (4)0.0044 (4)0.0004 (4)
C20.0165 (5)0.0170 (5)0.0171 (5)0.0005 (4)0.0032 (4)0.0004 (4)
C30.0144 (5)0.0178 (5)0.0170 (5)0.0007 (4)0.0025 (4)0.0004 (4)
C40.0178 (5)0.0178 (6)0.0189 (6)0.0006 (4)0.0034 (4)0.0006 (5)
C50.0213 (6)0.0222 (6)0.0200 (6)0.0027 (5)0.0020 (5)0.0031 (5)
C60.0224 (6)0.0272 (7)0.0163 (6)0.0009 (5)0.0000 (5)0.0008 (5)
C70.0203 (6)0.0227 (6)0.0174 (6)0.0008 (5)0.0012 (5)0.0032 (5)
C80.0150 (5)0.0169 (6)0.0189 (6)0.0007 (4)0.0030 (4)0.0003 (4)
C90.0199 (6)0.0171 (6)0.0209 (6)0.0002 (4)0.0055 (5)0.0033 (5)
C100.0255 (6)0.0238 (6)0.0201 (6)0.0054 (5)0.0044 (5)0.0004 (5)
C110.0211 (6)0.0310 (7)0.0258 (7)0.0063 (5)0.0025 (5)0.0024 (6)
C120.0219 (6)0.0227 (6)0.0324 (7)0.0008 (5)0.0075 (5)0.0036 (6)
C130.0255 (7)0.0231 (6)0.0278 (7)0.0008 (5)0.0087 (5)0.0037 (5)
C140.0218 (6)0.0219 (6)0.0226 (6)0.0013 (5)0.0033 (5)0.0015 (5)
C150.0258 (6)0.0176 (6)0.0186 (6)0.0026 (5)0.0047 (5)0.0025 (5)
C160.0242 (6)0.0197 (6)0.0173 (6)0.0038 (5)0.0015 (5)0.0015 (5)
C170.0327 (7)0.0235 (7)0.0222 (6)0.0042 (6)0.0006 (5)0.0026 (5)
C180.0353 (8)0.0285 (7)0.0284 (7)0.0109 (6)0.0052 (6)0.0019 (6)
C190.0244 (7)0.0380 (8)0.0299 (8)0.0064 (6)0.0037 (6)0.0095 (7)
C200.0252 (7)0.0334 (8)0.0317 (8)0.0019 (6)0.0009 (6)0.0039 (6)
C210.0256 (7)0.0227 (7)0.0269 (7)0.0018 (5)0.0017 (5)0.0013 (5)
C220.0194 (6)0.0205 (6)0.0170 (5)0.0018 (5)0.0025 (4)0.0001 (5)
C230.0261 (6)0.0214 (6)0.0157 (6)0.0035 (5)0.0013 (5)0.0005 (5)
C240.0221 (6)0.0219 (6)0.0180 (6)0.0032 (5)0.0024 (5)0.0019 (5)
C250.0378 (8)0.0271 (7)0.0171 (6)0.0044 (6)0.0030 (5)0.0067 (5)
C260.0492 (9)0.0227 (7)0.0239 (7)0.0045 (6)0.0121 (7)0.0036 (6)
Geometric parameters (Å, º) top
S1—O11.4257 (10)C12—C131.389 (2)
S1—O21.4288 (10)C12—H120.95
S1—N11.6889 (11)C13—C141.3853 (19)
S1—C91.7574 (13)C13—H130.95
O3—C241.2118 (16)C14—H140.95
O4—C241.3443 (16)C15—C161.5220 (19)
O4—C251.4510 (16)C15—H15A0.99
N1—C11.4118 (16)C15—H15B0.99
N1—C81.4210 (16)C16—C211.391 (2)
C1—C21.3794 (18)C16—C171.3913 (19)
C1—C151.4984 (17)C17—C181.389 (2)
C2—C221.4436 (18)C17—H170.95
C2—C31.4503 (17)C18—C191.384 (2)
C3—C41.4004 (18)C18—H180.95
C3—C81.4051 (17)C19—C201.387 (2)
C4—C51.3830 (18)C19—H190.95
C4—H40.95C20—C211.394 (2)
C5—C61.3980 (19)C20—H200.95
C5—H50.95C21—H210.95
C6—C71.3842 (19)C22—C231.3418 (18)
C6—H60.95C22—H220.95
C7—C81.3930 (18)C23—C241.4722 (18)
C7—H70.95C23—H230.95
C9—C101.3935 (19)C25—C261.500 (2)
C9—C141.3954 (19)C25—H25A0.99
C10—C111.389 (2)C25—H25B0.99
C10—H100.95C26—H26A0.98
C11—C121.384 (2)C26—H26B0.98
C11—H110.95C26—H26C0.98
O1—S1—O2120.60 (6)C13—C14—C9118.74 (12)
O1—S1—N1106.74 (6)C13—C14—H14120.6
O2—S1—N1105.69 (6)C9—C14—H14120.6
O1—S1—C9109.27 (6)C1—C15—C16114.81 (11)
O2—S1—C9108.51 (6)C1—C15—H15A108.6
N1—S1—C9104.87 (6)C16—C15—H15A108.6
C24—O4—C25114.90 (11)C1—C15—H15B108.6
C1—N1—C8108.36 (10)C16—C15—H15B108.6
C1—N1—S1127.73 (9)H15A—C15—H15B107.5
C8—N1—S1123.44 (9)C21—C16—C17118.73 (13)
C2—C1—N1108.71 (11)C21—C16—C15122.10 (12)
C2—C1—C15126.67 (11)C17—C16—C15119.15 (12)
N1—C1—C15124.62 (11)C18—C17—C16120.63 (15)
C1—C2—C22122.85 (12)C18—C17—H17119.7
C1—C2—C3107.92 (11)C16—C17—H17119.7
C22—C2—C3129.23 (12)C19—C18—C17120.32 (14)
C4—C3—C8119.31 (11)C19—C18—H18119.8
C4—C3—C2133.18 (12)C17—C18—H18119.8
C8—C3—C2107.48 (11)C18—C19—C20119.64 (14)
C5—C4—C3118.96 (12)C18—C19—H19120.2
C5—C4—H4120.5C20—C19—H19120.2
C3—C4—H4120.5C19—C20—C21119.97 (15)
C4—C5—C6120.81 (12)C19—C20—H20120.0
C4—C5—H5119.6C21—C20—H20120.0
C6—C5—H5119.6C16—C21—C20120.67 (14)
C7—C6—C5121.38 (12)C16—C21—H21119.7
C7—C6—H6119.3C20—C21—H21119.7
C5—C6—H6119.3C23—C22—C2128.59 (12)
C6—C7—C8117.60 (12)C23—C22—H22115.7
C6—C7—H7121.2C2—C22—H22115.7
C8—C7—H7121.2C22—C23—C24119.08 (12)
C7—C8—C3121.90 (12)C22—C23—H23120.5
C7—C8—N1130.59 (12)C24—C23—H23120.5
C3—C8—N1107.51 (11)O3—C24—O4122.91 (12)
C10—C9—C14121.43 (12)O3—C24—C23125.98 (13)
C10—C9—S1119.31 (10)O4—C24—C23111.10 (11)
C14—C9—S1119.26 (10)O4—C25—C26107.16 (12)
C11—C10—C9118.86 (13)O4—C25—H25A110.3
C11—C10—H10120.6C26—C25—H25A110.3
C9—C10—H10120.6O4—C25—H25B110.3
C12—C11—C10120.13 (13)C26—C25—H25B110.3
C12—C11—H11119.9H25A—C25—H25B108.5
C10—C11—H11119.9C25—C26—H26A109.5
C11—C12—C13120.56 (13)C25—C26—H26B109.5
C11—C12—H12119.7H26A—C26—H26B109.5
C13—C12—H12119.7C25—C26—H26C109.5
C14—C13—C12120.27 (13)H26A—C26—H26C109.5
C14—C13—H13119.9H26B—C26—H26C109.5
C12—C13—H13119.9
O1—S1—N1—C122.55 (12)O2—S1—C9—C10148.51 (11)
O2—S1—N1—C1152.10 (11)N1—S1—C9—C1098.91 (11)
C9—S1—N1—C193.33 (11)O1—S1—C9—C14164.62 (10)
O1—S1—N1—C8166.17 (10)O2—S1—C9—C1431.32 (12)
O2—S1—N1—C836.63 (11)N1—S1—C9—C1481.26 (11)
C9—S1—N1—C877.95 (11)C14—C9—C10—C111.3 (2)
C8—N1—C1—C21.03 (14)S1—C9—C10—C11178.86 (11)
S1—N1—C1—C2173.37 (9)C9—C10—C11—C120.2 (2)
C8—N1—C1—C15178.99 (11)C10—C11—C12—C131.2 (2)
S1—N1—C1—C156.66 (18)C11—C12—C13—C141.6 (2)
N1—C1—C2—C22178.70 (11)C12—C13—C14—C90.5 (2)
C15—C1—C2—C221.3 (2)C10—C9—C14—C131.0 (2)
N1—C1—C2—C31.33 (14)S1—C9—C14—C13179.21 (11)
C15—C1—C2—C3178.70 (12)C2—C1—C15—C1698.29 (15)
C1—C2—C3—C4176.70 (13)N1—C1—C15—C1681.74 (15)
C22—C2—C3—C43.3 (2)C1—C15—C16—C2124.17 (18)
C1—C2—C3—C81.14 (14)C1—C15—C16—C17157.46 (12)
C22—C2—C3—C8178.89 (12)C21—C16—C17—C181.6 (2)
C8—C3—C4—C50.24 (18)C15—C16—C17—C18179.96 (13)
C2—C3—C4—C5177.87 (13)C16—C17—C18—C190.0 (2)
C3—C4—C5—C61.37 (19)C17—C18—C19—C201.1 (2)
C4—C5—C6—C71.5 (2)C18—C19—C20—C210.5 (2)
C5—C6—C7—C80.0 (2)C17—C16—C21—C202.2 (2)
C6—C7—C8—C31.65 (19)C15—C16—C21—C20179.43 (13)
C6—C7—C8—N1177.70 (12)C19—C20—C21—C161.1 (2)
C4—C3—C8—C71.79 (18)C1—C2—C22—C23176.57 (13)
C2—C3—C8—C7179.98 (11)C3—C2—C22—C233.5 (2)
C4—C3—C8—N1177.69 (11)C2—C22—C23—C24177.74 (13)
C2—C3—C8—N10.50 (13)C25—O4—C24—O30.3 (2)
C1—N1—C8—C7179.12 (13)C25—O4—C24—C23179.10 (12)
S1—N1—C8—C76.38 (19)C22—C23—C24—O31.0 (2)
C1—N1—C8—C30.31 (13)C22—C23—C24—O4178.39 (12)
S1—N1—C8—C3173.04 (8)C24—O4—C25—C26171.93 (13)
O1—S1—C9—C1015.21 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O20.952.362.9424 (17)119
C15—H15A···O10.992.242.8474 (17)118
C18—H18···O3i0.952.593.282 (2)130
C10—H10···Cg10.952.753.3524 (14)122
C11—H11···Cg2ii0.952.813.6263 (15)145
Symmetry codes: (i) x, y+1, z; (ii) x, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC26H23NO4S
Mr445.51
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)11.4683 (2), 8.8983 (1), 21.5088 (3)
β (°) 99.406 (1)
V3)2165.43 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.28 × 0.25 × 0.24
Data collection
DiffractometerBruker SMART APEX2 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.912, 0.958
No. of measured, independent and
observed [I > 2σ(I)] reflections
47728, 7943, 5869
Rint0.060
(sin θ/λ)max1)0.760
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.119, 1.06
No. of reflections7943
No. of parameters290
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.54

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O20.952.362.9424 (17)119
C15—H15A···O10.992.242.8474 (17)118
C18—H18···O3i0.952.593.282 (2)130
C10—H10···Cg10.952.753.3524 (14)122
C11—H11···Cg2ii0.952.813.6263 (15)145
Symmetry codes: (i) x, y+1, z; (ii) x, y1/2, z+1/2.
 

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