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In the title compound, C23H21NO3S, the planar indole ring system is oriented at an angle of 77.7 (1)° to the sulfonyl-bound benzene ring and 80.1 (1)° to the methoxy­phenyl group. The mol­ecular structure is stabilized by intra­molecular C—H...O inter­actions. In addition to van der Waals forces, the mol­ecular packing is controlled by a weak C—H...π inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045369/is2208sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045369/is2208Isup2.hkl
Contains datablock I

CCDC reference: 663819

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.126
  • Data-to-parameter ratio = 21.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg.
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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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

Indole compounds are used as bioactive drugs (Stevenson et al., 2000). The indole derivatives exhibit antituberculosis (Karali et al., 2007), anti-HIV (Ragno et al., 2006), central nervous system depressant and muscle relaxant properties (Harris & Uhle, 1960; Ho et al., 1986). Herein, we report the crystal structure of the title compound, (I).

In the molecule, the planar sulfonyl bound phenyl group subtends an angle of 77.7 (1)° with the planar indole moiety. The methyl atom is deviated from the indole ring by 0.075 (3) Å. The bond lengths and bond angles in the molecule are comparable with the values reported in literature (Palani et al., 2006a,b). The methoxy group also lies in the plane of the benzyl ring. The methoxybenzyl group is oriented at angle of 80.1 (1)° with respect to the indole moiety. The geometry around S1 is distorted from tetrahedral values. The widening of the angle (O1—S1—O2=) 119.46 (8)° and narrowing of the angle (N1—S1—C9=) 105.19 (6)° are due to the electon withdrawing character of the phenyl sulfonyl group. The sum of the bond angle around N1 indicates that the atom is in an sp2 hybridized state.

A few C—H···O intramolecular interactions play the role to stabilize the molecules in addition to a C—H···π interaction (Table 1). The molecules in the unit cell are packed by van der Waals forces.

Related literature top

For related literature, see: Harris & Uhle (1960); Ho et al. (1986); Karali et al. (2007); Palani et al. (2006a,b); Ragno et al. (2006); Stevenson et al. (2000).

Experimental top

1-Phenylsulfonyl-3-methyl-2-bromomethylindole (2 g, 5.49 mmol) was dissolved in dry CH3CN (20 ml). To this anisole (0.89 ml, 8.23 mmol), ZnBr2 (2.47 g, 10.96 mmol) were added and refluxed for 24 h. The reaction mixture was quenched with ice containing few drops of conc. HCl, extracted with CHCl3 (3 × 5 ml) and dried Na2SO4. The solvent was removed under vacuo. Then crude was recrystallized from 5% ethyl acetate / hexane (5:95) to get the diffraction quality crystals.

Refinement top

The H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.98 Å, and with Uiso= 1.5Ueq(C) for methyl H and 1.2Ueq(C) for other H.

Structure description top

Indole compounds are used as bioactive drugs (Stevenson et al., 2000). The indole derivatives exhibit antituberculosis (Karali et al., 2007), anti-HIV (Ragno et al., 2006), central nervous system depressant and muscle relaxant properties (Harris & Uhle, 1960; Ho et al., 1986). Herein, we report the crystal structure of the title compound, (I).

In the molecule, the planar sulfonyl bound phenyl group subtends an angle of 77.7 (1)° with the planar indole moiety. The methyl atom is deviated from the indole ring by 0.075 (3) Å. The bond lengths and bond angles in the molecule are comparable with the values reported in literature (Palani et al., 2006a,b). The methoxy group also lies in the plane of the benzyl ring. The methoxybenzyl group is oriented at angle of 80.1 (1)° with respect to the indole moiety. The geometry around S1 is distorted from tetrahedral values. The widening of the angle (O1—S1—O2=) 119.46 (8)° and narrowing of the angle (N1—S1—C9=) 105.19 (6)° are due to the electon withdrawing character of the phenyl sulfonyl group. The sum of the bond angle around N1 indicates that the atom is in an sp2 hybridized state.

A few C—H···O intramolecular interactions play the role to stabilize the molecules in addition to a C—H···π interaction (Table 1). The molecules in the unit cell are packed by van der Waals forces.

For related literature, see: Harris & Uhle (1960); Ho et al. (1986); Karali et al. (2007); Palani et al. (2006a,b); Ragno et al. (2006); Stevenson et al. (2000).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (I), with 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The molecular packing of (I), viewed approximately along the a axis. Dashed lines indicate C—H···O hydrogen bonds.
2-(4-Methoxybenzyl)-3-methyl-1-phenylsulfonyl-1H-indole top
Crystal data top
C23H21NO3SZ = 2
Mr = 391.47F(000) = 412
Triclinic, P1Dx = 1.298 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2518 (3) ÅCell parameters from 14224 reflections
b = 10.0817 (4) Åθ = 2.0–27.5°
c = 12.8169 (5) ŵ = 0.19 mm1
α = 97.244 (2)°T = 293 K
β = 97.876 (2)°Needle, colourless
γ = 105.709 (2)°0.24 × 0.20 × 0.18 mm
V = 1001.76 (7) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4234 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 29.2°, θmin = 1.6°
ω scansh = 1111
23750 measured reflectionsk = 1313
5432 independent reflectionsl = 1717
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0596P)2 + 0.1977P]
where P = (Fo2 + 2Fc2)/3
5432 reflections(Δ/σ)max < 0.001
254 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C23H21NO3Sγ = 105.709 (2)°
Mr = 391.47V = 1001.76 (7) Å3
Triclinic, P1Z = 2
a = 8.2518 (3) ÅMo Kα radiation
b = 10.0817 (4) ŵ = 0.19 mm1
c = 12.8169 (5) ÅT = 293 K
α = 97.244 (2)°0.24 × 0.20 × 0.18 mm
β = 97.876 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4234 reflections with I > 2σ(I)
23750 measured reflectionsRint = 0.024
5432 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.04Δρmax = 0.26 e Å3
5432 reflectionsΔρmin = 0.26 e Å3
254 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
S10.36424 (4)0.91092 (4)0.76283 (3)0.05054 (12)
N10.37371 (14)0.75504 (11)0.70911 (9)0.0427 (2)
O10.46782 (14)1.00993 (11)0.71146 (12)0.0716 (4)
O20.40232 (17)0.92234 (13)0.87515 (10)0.0754 (4)
O31.06112 (15)0.70612 (13)1.03001 (10)0.0685 (3)
C10.32438 (17)0.63013 (14)0.75472 (11)0.0463 (3)
C20.2657 (2)0.51995 (16)0.67479 (14)0.0604 (4)
C30.2704 (2)0.56945 (17)0.57476 (13)0.0593 (4)
C40.33517 (17)0.71415 (15)0.59622 (11)0.0469 (3)
C50.3562 (2)0.7930 (2)0.51567 (14)0.0644 (4)
H50.39890.89000.53070.077*
C60.3111 (3)0.7213 (3)0.41179 (16)0.0882 (7)
H60.32420.77120.35570.106*
C70.2472 (4)0.5779 (3)0.38937 (17)0.1049 (8)
H70.21800.53290.31860.126*
C80.2258 (3)0.5004 (2)0.46920 (17)0.0933 (7)
H80.18230.40350.45340.112*
C90.15053 (16)0.90762 (13)0.72524 (11)0.0431 (3)
C100.1117 (2)0.99273 (17)0.65585 (14)0.0581 (4)
H100.19721.04990.62750.070*
C110.0566 (2)0.9916 (2)0.62901 (15)0.0691 (5)
H110.08481.04960.58310.083*
C120.1822 (2)0.9055 (2)0.66976 (15)0.0659 (4)
H120.29550.90410.65040.079*
C130.1415 (2)0.8215 (2)0.73890 (16)0.0681 (5)
H130.22740.76370.76660.082*
C140.0248 (2)0.82196 (18)0.76742 (14)0.0585 (4)
H140.05260.76530.81460.070*
C150.35876 (19)0.62830 (19)0.87222 (12)0.0560 (4)
H15A0.29360.53850.88580.067*
H15B0.31900.69980.90950.067*
C160.54654 (18)0.65305 (16)0.91723 (10)0.0475 (3)
C170.6286 (2)0.55505 (15)0.88721 (12)0.0515 (3)
H170.56730.47390.83940.062*
C180.7990 (2)0.57510 (15)0.92664 (12)0.0534 (3)
H180.85130.50780.90530.064*
C190.89245 (19)0.69517 (15)0.99790 (11)0.0491 (3)
C200.8126 (2)0.79269 (17)1.03037 (12)0.0586 (4)
H200.87340.87301.07920.070*
C210.6407 (2)0.77048 (18)0.98990 (12)0.0586 (4)
H210.58760.83671.01250.070*
C221.1655 (3)0.8269 (2)1.10098 (18)0.0878 (6)
H22A1.27990.82021.11640.132*
H22B1.12090.83471.16610.132*
H22C1.16670.90801.06870.132*
C230.2103 (4)0.3676 (2)0.6834 (2)0.1025 (8)
H23A0.29180.32380.65980.154*
H23B0.09990.32330.63950.154*
H23C0.20380.35820.75650.154*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.04216 (18)0.04139 (19)0.0631 (2)0.01361 (14)0.00070 (15)0.00118 (15)
N10.0429 (5)0.0413 (6)0.0453 (6)0.0153 (4)0.0078 (4)0.0064 (4)
O10.0431 (5)0.0430 (6)0.1228 (11)0.0036 (4)0.0136 (6)0.0136 (6)
O20.0846 (8)0.0748 (8)0.0606 (7)0.0414 (7)0.0173 (6)0.0175 (6)
O30.0590 (6)0.0716 (8)0.0720 (7)0.0274 (6)0.0035 (5)0.0002 (6)
C10.0425 (6)0.0470 (7)0.0518 (7)0.0139 (6)0.0107 (5)0.0135 (6)
C20.0661 (9)0.0444 (8)0.0640 (9)0.0080 (7)0.0052 (7)0.0098 (7)
C30.0663 (9)0.0534 (9)0.0530 (8)0.0158 (7)0.0042 (7)0.0011 (7)
C40.0427 (6)0.0529 (8)0.0463 (7)0.0164 (6)0.0079 (5)0.0086 (6)
C50.0602 (9)0.0751 (11)0.0613 (9)0.0189 (8)0.0116 (7)0.0257 (8)
C60.0914 (14)0.125 (2)0.0543 (10)0.0340 (14)0.0154 (10)0.0323 (12)
C70.135 (2)0.124 (2)0.0474 (10)0.0387 (18)0.0052 (12)0.0045 (12)
C80.126 (2)0.0763 (13)0.0622 (11)0.0247 (13)0.0018 (12)0.0128 (10)
C90.0411 (6)0.0407 (6)0.0489 (7)0.0153 (5)0.0091 (5)0.0052 (5)
C100.0521 (8)0.0566 (9)0.0760 (10)0.0221 (7)0.0195 (7)0.0271 (8)
C110.0643 (10)0.0824 (12)0.0777 (11)0.0404 (9)0.0148 (8)0.0316 (10)
C120.0450 (8)0.0816 (12)0.0772 (11)0.0286 (8)0.0134 (7)0.0108 (9)
C130.0506 (8)0.0762 (11)0.0874 (13)0.0206 (8)0.0307 (8)0.0260 (10)
C140.0575 (8)0.0640 (9)0.0662 (9)0.0255 (7)0.0231 (7)0.0261 (8)
C150.0530 (8)0.0702 (10)0.0513 (8)0.0207 (7)0.0167 (6)0.0205 (7)
C160.0545 (7)0.0562 (8)0.0395 (6)0.0218 (6)0.0143 (6)0.0173 (6)
C170.0616 (8)0.0437 (7)0.0499 (7)0.0166 (6)0.0080 (6)0.0101 (6)
C180.0655 (9)0.0476 (7)0.0538 (8)0.0277 (7)0.0092 (7)0.0102 (6)
C190.0566 (8)0.0526 (8)0.0424 (7)0.0226 (6)0.0066 (6)0.0126 (6)
C200.0703 (10)0.0580 (9)0.0466 (7)0.0276 (8)0.0002 (7)0.0024 (6)
C210.0705 (10)0.0664 (10)0.0467 (7)0.0372 (8)0.0092 (7)0.0012 (7)
C220.0695 (12)0.0920 (15)0.0846 (13)0.0189 (11)0.0098 (10)0.0116 (11)
C230.130 (2)0.0469 (10)0.1088 (18)0.0001 (11)0.0013 (15)0.0169 (11)
Geometric parameters (Å, º) top
S1—O21.4139 (13)C11—C121.370 (3)
S1—O11.4208 (13)C11—H110.9300
S1—N11.6607 (11)C12—C131.370 (3)
S1—C91.7534 (13)C12—H120.9300
N1—C41.4202 (17)C13—C141.370 (2)
N1—C11.4376 (17)C13—H130.9300
O3—C191.3664 (18)C14—H140.9300
O3—C221.411 (2)C15—C161.518 (2)
C1—C21.343 (2)C15—H15A0.9700
C1—C151.497 (2)C15—H15B0.9700
C2—C31.435 (2)C16—C211.378 (2)
C2—C231.502 (2)C16—C171.386 (2)
C3—C41.388 (2)C17—C181.378 (2)
C3—C81.392 (2)C17—H170.9300
C4—C51.382 (2)C18—C191.384 (2)
C5—C61.382 (3)C18—H180.9300
C5—H50.9300C19—C201.378 (2)
C6—C71.375 (4)C20—C211.389 (2)
C6—H60.9300C20—H200.9300
C7—C81.366 (3)C21—H210.9300
C7—H70.9300C22—H22A0.9600
C8—H80.9300C22—H22B0.9600
C9—C101.376 (2)C22—H22C0.9600
C9—C141.378 (2)C23—H23A0.9600
C10—C111.381 (2)C23—H23B0.9600
C10—H100.9300C23—H23C0.9600
O2—S1—O1119.46 (8)C11—C12—H12119.9
O2—S1—N1107.52 (7)C13—C12—H12119.9
O1—S1—N1106.30 (7)C14—C13—C12120.39 (15)
O2—S1—C9109.12 (7)C14—C13—H13119.8
O1—S1—C9108.34 (7)C12—C13—H13119.8
N1—S1—C9105.19 (6)C13—C14—C9119.12 (14)
C4—N1—C1107.26 (11)C13—C14—H14120.4
C4—N1—S1119.34 (9)C9—C14—H14120.4
C1—N1—S1124.73 (9)C1—C15—C16113.44 (12)
C19—O3—C22118.68 (14)C1—C15—H15A108.9
C2—C1—N1108.44 (12)C16—C15—H15A108.9
C2—C1—C15127.66 (14)C1—C15—H15B108.9
N1—C1—C15123.39 (13)C16—C15—H15B108.9
C1—C2—C3108.85 (14)H15A—C15—H15B107.7
C1—C2—C23127.78 (17)C21—C16—C17117.55 (14)
C3—C2—C23123.32 (17)C21—C16—C15122.13 (13)
C4—C3—C8119.54 (17)C17—C16—C15120.31 (14)
C4—C3—C2108.13 (14)C18—C17—C16121.48 (14)
C8—C3—C2132.33 (18)C18—C17—H17119.3
C5—C4—C3122.00 (15)C16—C17—H17119.3
C5—C4—N1130.70 (15)C17—C18—C19120.15 (13)
C3—C4—N1107.29 (12)C17—C18—H18119.9
C4—C5—C6117.04 (19)C19—C18—H18119.9
C4—C5—H5121.5O3—C19—C20125.29 (14)
C6—C5—H5121.5O3—C19—C18115.38 (13)
C7—C6—C5121.58 (19)C20—C19—C18119.33 (14)
C7—C6—H6119.2C19—C20—C21119.66 (14)
C5—C6—H6119.2C19—C20—H20120.2
C8—C7—C6121.2 (2)C21—C20—H20120.2
C8—C7—H7119.4C16—C21—C20121.81 (14)
C6—C7—H7119.4C16—C21—H21119.1
C7—C8—C3118.6 (2)C20—C21—H21119.1
C7—C8—H8120.7O3—C22—H22A109.5
C3—C8—H8120.7O3—C22—H22B109.5
C10—C9—C14121.16 (13)H22A—C22—H22B109.5
C10—C9—S1119.39 (11)O3—C22—H22C109.5
C14—C9—S1119.44 (11)H22A—C22—H22C109.5
C9—C10—C11118.78 (15)H22B—C22—H22C109.5
C9—C10—H10120.6C2—C23—H23A109.5
C11—C10—H10120.6C2—C23—H23B109.5
C12—C11—C10120.27 (15)H23A—C23—H23B109.5
C12—C11—H11119.9C2—C23—H23C109.5
C10—C11—H11119.9H23A—C23—H23C109.5
C11—C12—C13120.28 (15)H23B—C23—H23C109.5
O2—S1—N1—C4178.01 (11)C2—C3—C8—C7179.2 (2)
O1—S1—N1—C452.97 (12)O2—S1—C9—C10132.11 (13)
C9—S1—N1—C461.81 (11)O1—S1—C9—C100.56 (15)
O2—S1—N1—C134.54 (13)N1—S1—C9—C10112.79 (13)
O1—S1—N1—C1163.56 (11)O2—S1—C9—C1446.57 (14)
C9—S1—N1—C181.67 (11)O1—S1—C9—C14178.11 (12)
C4—N1—C1—C22.16 (15)N1—S1—C9—C1468.54 (13)
S1—N1—C1—C2149.25 (12)C14—C9—C10—C110.2 (2)
C4—N1—C1—C15174.49 (12)S1—C9—C10—C11178.41 (13)
S1—N1—C1—C1538.42 (17)C9—C10—C11—C121.0 (3)
N1—C1—C2—C31.54 (18)C10—C11—C12—C131.1 (3)
C15—C1—C2—C3173.45 (14)C11—C12—C13—C140.4 (3)
N1—C1—C2—C23175.7 (2)C12—C13—C14—C90.3 (3)
C15—C1—C2—C233.8 (3)C10—C9—C14—C130.4 (2)
C1—C2—C3—C40.3 (2)S1—C9—C14—C13179.05 (13)
C23—C2—C3—C4177.07 (19)C2—C1—C15—C1699.95 (19)
C1—C2—C3—C8179.5 (2)N1—C1—C15—C1670.85 (18)
C23—C2—C3—C82.1 (3)C1—C15—C16—C21114.27 (16)
C8—C3—C4—C50.4 (3)C1—C15—C16—C1766.92 (18)
C2—C3—C4—C5179.70 (15)C21—C16—C17—C181.3 (2)
C8—C3—C4—N1178.30 (17)C15—C16—C17—C18179.83 (13)
C2—C3—C4—N11.01 (17)C16—C17—C18—C190.0 (2)
C1—N1—C4—C5179.56 (15)C22—O3—C19—C201.0 (2)
S1—N1—C4—C530.4 (2)C22—O3—C19—C18178.76 (17)
C1—N1—C4—C31.91 (15)C17—C18—C19—O3178.49 (13)
S1—N1—C4—C3151.10 (11)C17—C18—C19—C201.3 (2)
C3—C4—C5—C60.5 (2)O3—C19—C20—C21178.59 (14)
N1—C4—C5—C6177.85 (16)C18—C19—C20—C211.1 (2)
C4—C5—C6—C70.3 (3)C17—C16—C21—C201.4 (2)
C5—C6—C7—C80.0 (4)C15—C16—C21—C20179.72 (14)
C6—C7—C8—C30.1 (4)C19—C20—C21—C160.2 (2)
C4—C3—C8—C70.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O10.932.392.970 (2)120
C15—H15B···O20.972.282.883 (2)119
C21—H21···O20.932.563.127 (2)120
C13—H13···Cgi0.932.773.527 (2)139
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC23H21NO3S
Mr391.47
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.2518 (3), 10.0817 (4), 12.8169 (5)
α, β, γ (°)97.244 (2), 97.876 (2), 105.709 (2)
V3)1001.76 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.24 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
23750, 5432, 4234
Rint0.024
(sin θ/λ)max1)0.687
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.126, 1.04
No. of reflections5432
No. of parameters254
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.26

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
C5—H5···O10.932.392.970 (2)120
C15—H15B···O20.972.282.883 (2)119
C21—H21···O20.932.563.127 (2)120
C13—H13···Cgi0.932.773.527 (2)139
Symmetry code: (i) x+1, y, z.
 

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