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In the title compound, C21H22N2O6S, the dihedral angle between the sulfonyl-bound phenyl ring and the indole ring system is 79.4 (1)°. The crystal packing is controlled by intra- and inter­molecular N—H...O, C—H...O and C—H...π inter­actions, in addition to van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047563/ci2467sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047563/ci2467Isup2.hkl
Contains datablock I

CCDC reference: 667284

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.042
  • wR factor = 0.132
  • Data-to-parameter ratio = 26.4

checkCIF/PLATON results

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Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.47 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.53 Ratio
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The indole ring system is present in a number of natural products. The indole derivatives show important medicinal properties such as anti-bacterial (Tiwari et al., 2006), anti-malarial (Kgokong et al., 2005), cytoprotective and radical scavenging activities (Mor et al., 2003). In view of the above importance, the crystal structure determination of the title compound was undertaken.

The C—C and C—N bond lengths in the indole ring system are comparable with those observed for related indole derivatives (Palani et al., 2007a,b). The indole ring system is planar, with a maximum deviation of 0.021 (1) Å for atom C2. The sum of the bond angle around N1 [359.9 °] indicates sp2 hybridization. The methoxy group is coplanar with the indole ring system [C23—O6—C8—C9 = 4.2 (2)°]. The phenyl ring of the phenylsulfonyl group is oriented at an angle of 79.4 (1)° to the indole ring system.

Atom S1 has a distorted tetrahedral geometry. The widening of the bond angle O1—S1—O2 [119.96 (6)°] and narrowing of the bond angle N1—S1—C10 [104.29 (5)°] are due to the electon withdrawing character of the phenylsulfonyl group.

The carboxyethyl group at C3 assumes an extended conformation as can be seen from the torsion angles C3—C20—O5—C21 [-179.19 (11)°] and C20—O5—C21—C22 [178.86 (16)°]. The C2—C16—N17—C18 torsion angle of -132.72 (13)° describes the conformation of the acetamido group.

The molecular and crystal structures are stabilized by C—H···O and N—H···O hydrogen bonds (Table 1 and Fig. 2). In addition, C—H···π intermolecular interactions involving the pyrrole (centroid Cg) ring is observed,

Related literature top

For medicinal properties of indoles, see: Kgokong et al. (2005); Mor et al. (2003); Tiwari et al. (2006). For related structures, see: Palani et al. (2007a,b).

Experimental top

Ethyl-1-phenylsulfonyl-5-methoxy-2-bromomethylindole-3-carboxylate (0.2 g, 0.44 mmol) was dissolved in dry CH3CN (10 ml). To this ZnBr2 (0.2 g, 0.88 mmol) was added and the reaction mixture was refluxed for 24 h. Then it was quenched with ice water (50 ml) containing few drops of concentrated HCl, extracted with CHCl3 (3 × 5 ml) and dried (Na2SO4). The solvent was removed under vacuo and the crude product was recrystallized from methanol.

Refinement top

H atoms were positioned geometrically and were treated as riding on their parent atoms, with N—H = 0.82 Å, C—H = 0.93–0.98 Å and Uiso(H) = 1.5Ueq(Cmethyl) or 1.2Ueq(C). The displacement parameters of atom C22 were restrained to approximate isotropic behaviour.

Structure description top

The indole ring system is present in a number of natural products. The indole derivatives show important medicinal properties such as anti-bacterial (Tiwari et al., 2006), anti-malarial (Kgokong et al., 2005), cytoprotective and radical scavenging activities (Mor et al., 2003). In view of the above importance, the crystal structure determination of the title compound was undertaken.

The C—C and C—N bond lengths in the indole ring system are comparable with those observed for related indole derivatives (Palani et al., 2007a,b). The indole ring system is planar, with a maximum deviation of 0.021 (1) Å for atom C2. The sum of the bond angle around N1 [359.9 °] indicates sp2 hybridization. The methoxy group is coplanar with the indole ring system [C23—O6—C8—C9 = 4.2 (2)°]. The phenyl ring of the phenylsulfonyl group is oriented at an angle of 79.4 (1)° to the indole ring system.

Atom S1 has a distorted tetrahedral geometry. The widening of the bond angle O1—S1—O2 [119.96 (6)°] and narrowing of the bond angle N1—S1—C10 [104.29 (5)°] are due to the electon withdrawing character of the phenylsulfonyl group.

The carboxyethyl group at C3 assumes an extended conformation as can be seen from the torsion angles C3—C20—O5—C21 [-179.19 (11)°] and C20—O5—C21—C22 [178.86 (16)°]. The C2—C16—N17—C18 torsion angle of -132.72 (13)° describes the conformation of the acetamido group.

The molecular and crystal structures are stabilized by C—H···O and N—H···O hydrogen bonds (Table 1 and Fig. 2). In addition, C—H···π intermolecular interactions involving the pyrrole (centroid Cg) ring is observed,

For medicinal properties of indoles, see: Kgokong et al. (2005); Mor et al. (2003); Tiwari et al. (2006). For related structures, see: Palani et al. (2007a,b).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. View of the C–H···O hydrogen-bonded (dashed lines) dimers in the title compound.
Ethyl 2-acetamidomethyl-5-methoxy-1-(phenylsulfonyl)indole-3-carboxylate top
Crystal data top
C21H22N2O6SF(000) = 904
Mr = 430.47Dx = 1.409 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 16928 reflections
a = 12.6551 (5) Åθ = 1.9–28.8°
b = 10.2166 (3) ŵ = 0.20 mm1
c = 16.0960 (6) ÅT = 293 K
β = 102.738 (2)°Black, colourless
V = 2029.87 (13) Å30.24 × 0.22 × 0.19 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5514 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 33.3°, θmin = 1.9°
ω scansh = 1918
28118 measured reflectionsk = 815
7225 independent reflectionsl = 2123
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0734P)2 + 0.3747P]
where P = (Fo2 + 2Fc2)/3
7225 reflections(Δ/σ)max = 0.001
274 parametersΔρmax = 0.38 e Å3
6 restraintsΔρmin = 0.27 e Å3
Crystal data top
C21H22N2O6SV = 2029.87 (13) Å3
Mr = 430.47Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.6551 (5) ŵ = 0.20 mm1
b = 10.2166 (3) ÅT = 293 K
c = 16.0960 (6) Å0.24 × 0.22 × 0.19 mm
β = 102.738 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5514 reflections with I > 2σ(I)
28118 measured reflectionsRint = 0.026
7225 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0426 restraints
wR(F2) = 0.132H-atom parameters constrained
S = 1.03Δρmax = 0.38 e Å3
7225 reflectionsΔρmin = 0.27 e Å3
274 parameters
Special details top

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
S10.25606 (2)0.24106 (3)0.033869 (19)0.03081 (8)
O10.23696 (9)0.26356 (9)0.11639 (6)0.0431 (2)
O20.22673 (9)0.33777 (9)0.03060 (6)0.0431 (2)
O30.29175 (9)0.26840 (10)0.23564 (8)0.0490 (3)
O40.00500 (9)0.24044 (10)0.14390 (7)0.0479 (3)
O50.00232 (8)0.06558 (9)0.22619 (6)0.0390 (2)
O60.12859 (10)0.34650 (10)0.17262 (7)0.0523 (3)
N10.18728 (8)0.10353 (9)0.00187 (6)0.02924 (19)
C20.13543 (9)0.06821 (10)0.08556 (7)0.0270 (2)
C30.09319 (9)0.05521 (11)0.08273 (7)0.0280 (2)
C40.12180 (9)0.10222 (11)0.00367 (7)0.0285 (2)
C50.17982 (9)0.00283 (11)0.05311 (7)0.0294 (2)
C60.21941 (11)0.01788 (13)0.14057 (8)0.0375 (3)
H60.25760.04880.17350.045*
C70.19976 (13)0.13540 (13)0.17626 (8)0.0415 (3)
H70.22580.14820.23440.050*
C80.14182 (12)0.23589 (12)0.12755 (9)0.0377 (3)
C90.10138 (11)0.22145 (12)0.04093 (8)0.0341 (2)
H90.06220.28800.00860.041*
C100.39255 (10)0.19783 (11)0.04459 (8)0.0319 (2)
C110.45391 (12)0.17032 (14)0.12542 (9)0.0427 (3)
H110.42300.17280.17270.051*
C120.56195 (13)0.13917 (18)0.13380 (11)0.0537 (4)
H120.60450.12070.18740.064*
C130.60697 (13)0.13532 (17)0.06364 (12)0.0557 (4)
H130.67990.11450.07020.067*
C140.54543 (13)0.16196 (17)0.01633 (12)0.0522 (4)
H140.57680.15820.06340.063*
C150.43683 (11)0.19438 (15)0.02690 (9)0.0412 (3)
H150.39480.21330.08060.049*
C160.13167 (10)0.15243 (12)0.16280 (7)0.0330 (2)
H16A0.05670.16690.19150.040*
H16B0.16380.23690.14500.040*
N170.18908 (10)0.09269 (11)0.22197 (7)0.0383 (2)
H170.17670.01170.23500.046*
C180.26035 (11)0.15747 (13)0.25727 (8)0.0367 (3)
C190.29745 (18)0.08422 (18)0.32656 (12)0.0623 (5)
H19A0.27280.12880.37980.094*
H19B0.26810.00280.33070.094*
H19C0.37510.07980.31350.094*
C200.02614 (9)0.13084 (12)0.15252 (8)0.0322 (2)
C210.06499 (15)0.13493 (17)0.29710 (10)0.0551 (4)
H21A0.13350.15900.28370.066*
H21B0.02890.21400.30950.066*
C220.0834 (3)0.0456 (2)0.37100 (13)0.0939 (9)
H22A0.11420.03480.35650.141*
H22B0.13220.08580.41820.141*
H22C0.01560.02780.38630.141*
C230.07613 (17)0.45528 (16)0.12610 (13)0.0608 (4)
H23A0.00310.43180.09920.091*
H23B0.07520.52730.16420.091*
H23C0.11460.48030.08340.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.03425 (15)0.02395 (13)0.03383 (15)0.00155 (10)0.00665 (11)0.00387 (10)
O10.0520 (6)0.0387 (5)0.0412 (5)0.0023 (4)0.0158 (4)0.0135 (4)
O20.0515 (6)0.0258 (4)0.0474 (5)0.0009 (4)0.0013 (4)0.0030 (4)
O30.0505 (6)0.0425 (5)0.0569 (6)0.0135 (4)0.0180 (5)0.0045 (4)
O40.0529 (6)0.0373 (5)0.0516 (6)0.0164 (4)0.0073 (5)0.0051 (4)
O50.0396 (5)0.0370 (4)0.0358 (4)0.0025 (4)0.0018 (4)0.0048 (4)
O60.0732 (8)0.0365 (5)0.0481 (6)0.0079 (5)0.0151 (5)0.0126 (4)
N10.0324 (5)0.0257 (4)0.0294 (4)0.0047 (3)0.0065 (4)0.0010 (3)
C20.0255 (5)0.0275 (5)0.0285 (5)0.0010 (4)0.0066 (4)0.0010 (4)
C30.0261 (5)0.0274 (5)0.0308 (5)0.0007 (4)0.0072 (4)0.0021 (4)
C40.0280 (5)0.0271 (5)0.0323 (5)0.0004 (4)0.0108 (4)0.0012 (4)
C50.0319 (5)0.0271 (5)0.0311 (5)0.0011 (4)0.0105 (4)0.0002 (4)
C60.0472 (7)0.0354 (6)0.0300 (5)0.0054 (5)0.0083 (5)0.0015 (4)
C70.0548 (8)0.0386 (6)0.0321 (6)0.0012 (6)0.0115 (6)0.0044 (5)
C80.0450 (7)0.0309 (5)0.0406 (6)0.0003 (5)0.0168 (5)0.0068 (5)
C90.0376 (6)0.0278 (5)0.0388 (6)0.0025 (4)0.0129 (5)0.0003 (4)
C100.0314 (5)0.0289 (5)0.0345 (5)0.0047 (4)0.0053 (4)0.0016 (4)
C110.0423 (7)0.0461 (7)0.0361 (6)0.0036 (6)0.0012 (5)0.0015 (5)
C120.0417 (7)0.0566 (9)0.0550 (9)0.0006 (7)0.0061 (7)0.0011 (7)
C130.0344 (7)0.0511 (9)0.0800 (12)0.0006 (6)0.0093 (7)0.0022 (8)
C140.0445 (8)0.0532 (9)0.0645 (10)0.0001 (7)0.0243 (7)0.0039 (7)
C150.0399 (7)0.0449 (7)0.0400 (6)0.0030 (5)0.0113 (5)0.0031 (5)
C160.0372 (6)0.0302 (5)0.0318 (5)0.0013 (4)0.0081 (5)0.0025 (4)
N170.0488 (6)0.0335 (5)0.0364 (5)0.0082 (4)0.0173 (5)0.0035 (4)
C180.0364 (6)0.0387 (6)0.0360 (6)0.0020 (5)0.0098 (5)0.0028 (5)
C190.0832 (13)0.0533 (9)0.0647 (10)0.0059 (9)0.0468 (10)0.0048 (8)
C200.0270 (5)0.0322 (5)0.0374 (6)0.0014 (4)0.0072 (4)0.0057 (4)
C210.0553 (9)0.0518 (8)0.0471 (8)0.0011 (7)0.0128 (7)0.0141 (7)
C220.146 (2)0.0566 (11)0.0529 (10)0.0219 (13)0.0351 (12)0.0046 (9)
C230.0755 (12)0.0346 (7)0.0720 (11)0.0107 (7)0.0155 (9)0.0103 (7)
Geometric parameters (Å, º) top
S1—O11.4203 (10)C11—C121.381 (2)
S1—O21.4216 (10)C11—H110.93
S1—N11.6858 (10)C12—C131.373 (3)
S1—C101.7542 (13)C12—H120.93
O3—C181.2257 (16)C13—C141.377 (3)
O4—C201.2052 (15)C13—H130.93
O5—C201.3356 (16)C14—C151.387 (2)
O5—C211.4497 (16)C14—H140.93
O6—C81.3728 (15)C15—H150.93
O6—C231.420 (2)C16—N171.4534 (16)
N1—C21.4092 (14)C16—H16A0.97
N1—C51.4176 (14)C16—H16B0.97
C2—C31.3742 (15)N17—C181.3417 (16)
C2—C161.5041 (15)N17—H170.86
C3—C41.4401 (16)C18—C191.502 (2)
C3—C201.4692 (16)C19—H19A0.96
C4—C51.3949 (16)C19—H19B0.96
C4—C91.4066 (16)C19—H19C0.96
C5—C61.3948 (17)C21—C221.476 (3)
C6—C71.3771 (18)C21—H21A0.97
C6—H60.93C21—H21B0.97
C7—C81.397 (2)C22—H22A0.96
C7—H70.93C22—H22B0.96
C8—C91.3831 (19)C22—H22C0.96
C9—H90.93C23—H23A0.96
C10—C151.3869 (18)C23—H23B0.96
C10—C111.3890 (18)C23—H23C0.96
O1—S1—O2119.96 (6)C14—C13—H13119.6
O1—S1—N1105.81 (5)C13—C14—C15120.19 (15)
O2—S1—N1107.35 (5)C13—C14—H14119.9
O1—S1—C10108.40 (6)C15—C14—H14119.9
O2—S1—C10109.86 (6)C10—C15—C14118.35 (14)
N1—S1—C10104.29 (5)C10—C15—H15120.8
C20—O5—C21115.68 (11)C14—C15—H15120.8
C8—O6—C23117.57 (12)N17—C16—C2111.85 (10)
C2—N1—C5108.62 (9)N17—C16—H16A109.2
C2—N1—S1129.51 (8)C2—C16—H16A109.2
C5—N1—S1121.76 (8)N17—C16—H16B109.2
C3—C2—N1107.81 (9)C2—C16—H16B109.2
C3—C2—C16127.64 (10)H16A—C16—H16B107.9
N1—C2—C16124.53 (10)C18—N17—C16123.38 (11)
C2—C3—C4108.74 (10)C18—N17—H17118.3
C2—C3—C20128.35 (10)C16—N17—H17118.3
C4—C3—C20122.88 (10)O3—C18—N17122.81 (13)
C5—C4—C9120.68 (11)O3—C18—C19122.46 (13)
C5—C4—C3107.26 (10)N17—C18—C19114.72 (12)
C9—C4—C3132.06 (11)C18—C19—H19A109.5
C6—C5—C4121.48 (11)C18—C19—H19B109.5
C6—C5—N1130.99 (11)H19A—C19—H19B109.5
C4—C5—N1107.52 (10)C18—C19—H19C109.5
C7—C6—C5117.35 (12)H19A—C19—H19C109.5
C7—C6—H6121.3H19B—C19—H19C109.5
C5—C6—H6121.3O4—C20—O5123.41 (12)
C6—C7—C8121.81 (12)O4—C20—C3123.29 (12)
C6—C7—H7119.1O5—C20—C3113.30 (10)
C8—C7—H7119.1O5—C21—C22107.04 (15)
O6—C8—C9124.01 (12)O5—C21—H21A110.3
O6—C8—C7114.73 (12)C22—C21—H21A110.3
C9—C8—C7121.26 (11)O5—C21—H21B110.3
C8—C9—C4117.40 (11)C22—C21—H21B110.3
C8—C9—H9121.3H21A—C21—H21B108.6
C4—C9—H9121.3C21—C22—H22A109.5
C15—C10—C11121.82 (12)C21—C22—H22B109.5
C15—C10—S1119.61 (10)H22A—C22—H22B109.5
C11—C10—S1118.56 (10)C21—C22—H22C109.5
C12—C11—C10118.37 (14)H22A—C22—H22C109.5
C12—C11—H11120.8H22B—C22—H22C109.5
C10—C11—H11120.8O6—C23—H23A109.5
C13—C12—C11120.50 (15)O6—C23—H23B109.5
C13—C12—H12119.7H23A—C23—H23B109.5
C11—C12—H12119.8O6—C23—H23C109.5
C12—C13—C14120.77 (15)H23A—C23—H23C109.5
C12—C13—H13119.6H23B—C23—H23C109.5
O1—S1—N1—C2147.04 (10)C6—C7—C8—C90.1 (2)
O2—S1—N1—C217.82 (12)O6—C8—C9—C4179.87 (12)
C10—S1—N1—C298.72 (11)C7—C8—C9—C40.6 (2)
O1—S1—N1—C537.20 (11)C5—C4—C9—C80.59 (18)
O2—S1—N1—C5166.41 (9)C3—C4—C9—C8179.49 (12)
C10—S1—N1—C577.05 (10)O1—S1—C10—C15168.10 (10)
C5—N1—C2—C32.07 (12)O2—S1—C10—C1535.28 (12)
S1—N1—C2—C3178.27 (8)N1—S1—C10—C1579.50 (11)
C5—N1—C2—C16176.42 (10)O1—S1—C10—C1110.68 (12)
S1—N1—C2—C160.22 (17)O2—S1—C10—C11143.50 (10)
N1—C2—C3—C42.20 (12)N1—S1—C10—C11101.72 (11)
C16—C2—C3—C4176.23 (11)C15—C10—C11—C120.2 (2)
N1—C2—C3—C20175.70 (11)S1—C10—C11—C12178.58 (12)
C16—C2—C3—C205.87 (19)C10—C11—C12—C130.2 (2)
C2—C3—C4—C51.51 (12)C11—C12—C13—C140.2 (3)
C20—C3—C4—C5176.53 (10)C12—C13—C14—C150.6 (3)
C2—C3—C4—C9178.56 (12)C11—C10—C15—C140.2 (2)
C20—C3—C4—C93.40 (19)S1—C10—C15—C14178.96 (12)
C9—C4—C5—C60.01 (18)C13—C14—C15—C100.6 (2)
C3—C4—C5—C6179.95 (11)C3—C2—C16—N1762.75 (15)
C9—C4—C5—N1179.85 (10)N1—C2—C16—N17115.43 (12)
C3—C4—C5—N10.21 (12)C2—C16—N17—C18132.72 (13)
C2—N1—C5—C6178.69 (13)C16—N17—C18—O38.1 (2)
S1—N1—C5—C62.14 (18)C16—N17—C18—C19170.97 (14)
C2—N1—C5—C41.13 (12)C21—O5—C20—O40.19 (19)
S1—N1—C5—C4177.68 (8)C21—O5—C20—C3179.19 (11)
C4—C5—C6—C70.53 (19)C2—C3—C20—O4178.17 (12)
N1—C5—C6—C7179.26 (12)C4—C3—C20—O44.20 (18)
C5—C6—C7—C80.5 (2)C2—C3—C20—O52.44 (17)
C23—O6—C8—C94.2 (2)C4—C3—C20—O5175.19 (10)
C23—O6—C8—C7176.27 (15)C20—O5—C21—C22178.86 (16)
C6—C7—C8—O6179.63 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···O50.862.382.852 (2)115
N17—H17···O3i0.862.583.402 (2)161
C6—H6···O10.932.372.917 (2)117
C7—H7···O1ii0.932.513.416 (2)164
C9—H9···O40.932.462.989 (2)116
C16—H16B···O20.972.112.904 (2)138
C23—H23B···O4iii0.962.533.267 (2)134
C13—H13···Cgiv0.932.793.647 (2)155
Symmetry codes: (i) x+1/2, y1/2, z1/2; (ii) x+1/2, y1/2, z+1/2; (iii) x, y1, z; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC21H22N2O6S
Mr430.47
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)12.6551 (5), 10.2166 (3), 16.0960 (6)
β (°) 102.738 (2)
V3)2029.87 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.24 × 0.22 × 0.19
Data collection
DiffractometerBruker Kappa APEXII CCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
28118, 7225, 5514
Rint0.026
(sin θ/λ)max1)0.772
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.132, 1.03
No. of reflections7225
No. of parameters274
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.27

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003), SHELXL97 (Sheldrick, 1997) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N17—H17···O50.862.382.852 (2)115
N17—H17···O3i0.862.583.402 (2)161
C6—H6···O10.932.372.917 (2)117
C7—H7···O1ii0.932.513.416 (2)164
C9—H9···O40.932.462.989 (2)116
C16—H16B···O20.972.112.904 (2)138
C23—H23B···O4iii0.962.533.267 (2)134
C13—H13···Cgiv0.932.793.647 (2)155
Symmetry codes: (i) x+1/2, y1/2, z1/2; (ii) x+1/2, y1/2, z+1/2; (iii) x, y1, z; (iv) x+1, y, z.
 

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