Ethyl (2-methyl-1-phenyl­sulfonyl-1H-indole-3-carbon­yl)acetate

Chakkaravarthi, G.; Dhayalan, V.; Mohanakrishnan, A.K.; Manivannan, V.

doi:10.1107/S1600536807037415

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Ethyl (2-methyl-1-phenylsulfonyl-1H-indole-3-carbonyl)acetate

G. Chakkaravarthi, V. Dhayalan, A. K. Mohanakrishnan and V. Manivannan

In the title compound, C₁₉H₁₇NO₅S, the phenyl ring forms a dihedral angle of 83.67 (4)° with the indole ring system. The molecular structure is stabilized by weak intramolecular C—H

O interactions and the crystal packing is stabilized by weak intermolecular C—H

O and C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037415/bt2458sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037415/bt2458Isup2.hkl Contains datablock I

CCDC reference: 660204

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R factor = 0.050
wR factor = 0.161
Data-to-parameter ratio = 25.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.06 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C18    -   C19    ...       1.43 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C16    -   C17    ...       1.53 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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

Phenylsulfonyl-indole compounds inhibit the HIV-1 RT enzyme in vitro and HTLVIIIb viral spread in MT-4 human T-lymphoid cells (Williams et al., 1993). Indole-3-carboxylate derivatives exhibit significant antihepatitis B virus activities (Chai et al., 2006).

The geometric parameters in the title compound (Fig. 1) agree with the reported values of similar structures (Liu et al., 2007; Senthil Kumar et al., 2006). The phenyl ring forms dihedral angle of 83.67 (4)° with the indole ring system. The five- (N1/C7/C8/C9/C14) and six- (C9–C14) membered rings in the indane group are planar, with a dihedral angle of 1.90 (4)° between these rings.

The sum of the bond angles around N1 (359.95°) indicates that N1 is sp²-hybridized. The torsion angles O2—S1—N1—C14 and O1—S1—N1—C7 [-44.24 (14)° and 9.30 (15)°, respectively] indicate the syn conformation of the sulfonyl moiety.

The details of the hydrogen bonding are given in Table 1. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O interactions and C—H···π interactions involving the C1–C6 (centroid Cg1) and N1/C7–C14 (centroid Cg2) rings.

A similar compound with dibromomethyl group has been reported (Rinderspacher et al., 2007).

Related literature top

For releted literature, see: Chai et al. (2006); Liu et al. (2007); Senthil Kumar et al. (2006); Williams et al. (1993). A similar compound with a dibromomethyl group has been reported recently (Rinderspacher et al., 2007).

Experimental top

To a solution of ethyl 2-(2-methyl-1H-indole-3-yl)-2-oxoacetate (10 g, 43.2 mmol) in dry dichloromethane (80 ml) under nitrogen, triethylamine (7.8 ml, 56.2 mmol) followed by dimethyl amino pyridine (0.52 g, 4.2 mmol) were added slowly and stirred at 273 K for 30 min. To this benzenesulfonyl chloride (8.3 ml, 64.9 mmol), dry dichloromethane (10 ml) was slowly added at 273 K for 30 min. Then the reaction mixture was stirred at room temperature and poured over crushed ice and extracted with dichloromethane (3 x 20 ml) and dried with sodium sulfate. The solvent was removed under vacuum. Then the crude product was recrystallized from methanol. Single crystals suitable for X-ray analysis were grown by slow evaporation of a methanol solution at room temperature.

Structure description top

A similar compound with dibromomethyl group has been reported (Rinderspacher et al., 2007).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Ethyl (2-methyl-1-phenylsulfonyl-1H-indole-3-carbonyl)acetate top

Crystal data top

C₁₉H₁₇NO₅S	F(000) = 776
M_r = 371.40	D_x = 1.410 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 26134 reflections
a = 9.6696 (4) Å	θ = 2.6–29.9°
b = 13.1526 (5) Å	µ = 0.22 mm⁻¹
c = 13.8048 (5) Å	T = 295 K
β = 94.898 (1)°	Block, colourless
V = 1749.29 (12) Å³	0.24 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	6064 independent reflections
Radiation source: fine-focus sealed tube	4222 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and φ scans	θ_max = 32.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.929, T_max = 0.958	k = −19→17
25430 measured reflections	l = −20→19

Refinement top

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0861P)² + 0.2836P] where P = (F_o² + 2F_c²)/3
6064 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₉H₁₇NO₅S	V = 1749.29 (12) Å³
M_r = 371.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.6696 (4) Å	µ = 0.22 mm⁻¹
b = 13.1526 (5) Å	T = 295 K
c = 13.8048 (5) Å	0.24 × 0.20 × 0.20 mm
β = 94.898 (1)°

Data collection top

Bruker Kappa APEXII diffractometer	6064 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4222 reflections with I > 2σ(I)
T_min = 0.929, T_max = 0.958	R_int = 0.025
25430 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.06	Δρ_max = 0.64 e Å⁻³
6064 reflections	Δρ_min = −0.33 e Å⁻³
237 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.22318 (4)	0.34233 (3)	0.23436 (3)	0.04290 (12)
O1	0.31603 (13)	0.42516 (11)	0.22844 (9)	0.0597 (3)
O2	0.26854 (14)	0.24114 (10)	0.21807 (9)	0.0583 (3)
O3	0.05279 (16)	0.40881 (12)	0.65463 (10)	0.0754 (5)
O4	0.37370 (15)	0.46654 (12)	0.63655 (13)	0.0749 (4)
O5	0.21527 (16)	0.58575 (10)	0.66369 (11)	0.0693 (4)
N1	0.17082 (13)	0.34280 (9)	0.34772 (9)	0.0388 (3)
C1	0.07099 (16)	0.36573 (12)	0.15947 (10)	0.0417 (3)
C2	0.0143 (2)	0.28885 (14)	0.10043 (15)	0.0578 (4)
H2	0.0542	0.2245	0.1016	0.069*
C3	−0.1034 (2)	0.31005 (19)	0.03940 (17)	0.0715 (6)
H3	−0.1422	0.2597	−0.0018	0.086*
C4	−0.1632 (2)	0.40435 (17)	0.03917 (16)	0.0676 (5)
H4	−0.2431	0.4172	−0.0014	0.081*
C5	−0.1066 (2)	0.47999 (17)	0.09798 (16)	0.0680 (5)
H5	−0.1480	0.5438	0.0972	0.082*
C6	0.0123 (2)	0.46155 (14)	0.15871 (13)	0.0546 (4)
H6	0.0520	0.5128	0.1983	0.066*
C7	0.19316 (14)	0.41714 (11)	0.42039 (10)	0.0371 (3)
C8	0.12836 (14)	0.38506 (11)	0.49973 (10)	0.0364 (3)
C9	0.05878 (14)	0.29003 (10)	0.47616 (10)	0.0357 (3)
C10	−0.01968 (16)	0.22449 (12)	0.52925 (11)	0.0446 (3)
H10	−0.0400	0.2408	0.5920	0.054*
C11	−0.06630 (19)	0.13474 (13)	0.48590 (14)	0.0539 (4)
H11	−0.1192	0.0903	0.5199	0.065*
C12	−0.0356 (2)	0.10986 (14)	0.39263 (14)	0.0564 (4)
H12	−0.0681	0.0487	0.3655	0.068*
C13	0.04189 (19)	0.17325 (13)	0.33887 (12)	0.0500 (4)
H13	0.0624	0.1560	0.2764	0.060*
C14	0.08790 (15)	0.26386 (11)	0.38203 (10)	0.0370 (3)
C15	0.2699 (2)	0.51382 (13)	0.40713 (13)	0.0523 (4)
H15A	0.2545	0.5597	0.4592	0.078*
H15B	0.2373	0.5443	0.3462	0.078*
H15C	0.3674	0.4997	0.4075	0.078*
C16	0.13428 (16)	0.43055 (12)	0.59581 (11)	0.0440 (3)
C17	0.25701 (18)	0.49730 (13)	0.63227 (12)	0.0484 (4)
C18	0.3215 (3)	0.6517 (2)	0.7133 (2)	0.0904 (8)
H18A	0.2796	0.6933	0.7609	0.109*
H18B	0.3928	0.6101	0.7474	0.109*
C19	0.3829 (4)	0.7157 (2)	0.6453 (3)	0.1093 (11)
H19A	0.4346	0.6749	0.6034	0.164*
H19B	0.4440	0.7634	0.6797	0.164*
H19C	0.3113	0.7519	0.6070	0.164*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03753 (19)	0.0552 (2)	0.03706 (19)	0.00035 (15)	0.00942 (14)	−0.00083 (15)
O1	0.0494 (6)	0.0800 (9)	0.0516 (7)	−0.0196 (6)	0.0145 (5)	0.0025 (6)
O2	0.0546 (7)	0.0659 (8)	0.0556 (7)	0.0185 (6)	0.0124 (6)	−0.0068 (6)
O3	0.0830 (10)	0.0882 (11)	0.0598 (8)	−0.0327 (8)	0.0346 (7)	−0.0305 (7)
O4	0.0513 (8)	0.0735 (10)	0.0966 (12)	0.0002 (7)	−0.0132 (7)	−0.0058 (8)
O5	0.0733 (9)	0.0544 (8)	0.0792 (10)	−0.0107 (6)	0.0011 (7)	−0.0210 (7)
N1	0.0429 (6)	0.0405 (6)	0.0335 (5)	−0.0052 (5)	0.0057 (5)	−0.0013 (5)
C1	0.0420 (7)	0.0498 (8)	0.0342 (6)	0.0002 (6)	0.0075 (5)	−0.0003 (6)
C2	0.0576 (10)	0.0490 (9)	0.0651 (11)	−0.0013 (8)	−0.0049 (8)	−0.0049 (8)
C3	0.0626 (12)	0.0702 (13)	0.0780 (14)	−0.0122 (10)	−0.0152 (10)	−0.0110 (11)
C4	0.0507 (10)	0.0789 (14)	0.0708 (13)	0.0028 (10)	−0.0082 (9)	0.0054 (11)
C5	0.0670 (12)	0.0669 (12)	0.0688 (12)	0.0197 (10)	−0.0020 (10)	0.0006 (10)
C6	0.0629 (11)	0.0533 (10)	0.0470 (9)	0.0080 (8)	0.0011 (8)	−0.0075 (7)
C7	0.0357 (6)	0.0361 (7)	0.0392 (7)	−0.0022 (5)	0.0022 (5)	−0.0003 (5)
C8	0.0362 (6)	0.0362 (6)	0.0368 (6)	−0.0011 (5)	0.0032 (5)	−0.0026 (5)
C9	0.0332 (6)	0.0374 (7)	0.0363 (6)	−0.0025 (5)	0.0018 (5)	−0.0004 (5)
C10	0.0435 (8)	0.0490 (8)	0.0419 (7)	−0.0093 (6)	0.0072 (6)	0.0007 (6)
C11	0.0547 (9)	0.0502 (9)	0.0570 (10)	−0.0180 (7)	0.0062 (8)	0.0049 (7)
C12	0.0657 (11)	0.0451 (9)	0.0575 (10)	−0.0182 (8)	0.0005 (8)	−0.0070 (7)
C13	0.0599 (10)	0.0465 (8)	0.0436 (8)	−0.0096 (7)	0.0049 (7)	−0.0082 (6)
C14	0.0370 (6)	0.0371 (7)	0.0366 (6)	−0.0032 (5)	0.0020 (5)	0.0000 (5)
C15	0.0599 (10)	0.0434 (8)	0.0541 (9)	−0.0150 (7)	0.0090 (8)	0.0007 (7)
C16	0.0465 (8)	0.0431 (8)	0.0429 (7)	−0.0048 (6)	0.0066 (6)	−0.0088 (6)
C17	0.0514 (9)	0.0490 (8)	0.0435 (8)	−0.0063 (7)	−0.0031 (7)	−0.0027 (7)
C18	0.114 (2)	0.0722 (16)	0.0828 (17)	−0.0360 (14)	−0.0062 (15)	−0.0201 (12)
C19	0.109 (2)	0.0856 (19)	0.127 (3)	−0.0298 (17)	−0.028 (2)	0.0274 (17)

Geometric parameters (Å, º) top

S1—O1	1.4185 (13)	C8—C9	1.4433 (19)
S1—O2	1.4251 (13)	C8—C16	1.452 (2)
S1—N1	1.6854 (12)	C9—C14	1.3960 (19)
S1—C1	1.7520 (16)	C9—C10	1.3967 (19)
O3—C16	1.2130 (19)	C10—C11	1.382 (2)
O4—C17	1.195 (2)	C10—H10	0.9300
O5—C17	1.317 (2)	C11—C12	1.385 (3)
O5—C18	1.468 (3)	C11—H11	0.9300
N1—C7	1.4042 (18)	C12—C13	1.379 (2)
N1—C14	1.4178 (18)	C12—H12	0.9300
C1—C6	1.382 (2)	C13—C14	1.389 (2)
C1—C2	1.382 (2)	C13—H13	0.9300
C2—C3	1.385 (3)	C15—H15A	0.9600
C2—H2	0.9300	C15—H15B	0.9600
C3—C4	1.368 (3)	C15—H15C	0.9600
C3—H3	0.9300	C16—C17	1.527 (2)
C4—C5	1.368 (3)	C18—C19	1.427 (4)
C4—H4	0.9300	C18—H18A	0.9700
C5—C6	1.385 (3)	C18—H18B	0.9700
C5—H5	0.9300	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C7—C8	1.3738 (19)	C19—H19C	0.9600
C7—C15	1.492 (2)

O1—S1—O2	120.22 (8)	C11—C10—H10	120.9
O1—S1—N1	107.01 (7)	C9—C10—H10	120.9
O2—S1—N1	105.72 (7)	C10—C11—C12	121.10 (15)
O1—S1—C1	109.57 (8)	C10—C11—H11	119.4
O2—S1—C1	108.98 (8)	C12—C11—H11	119.4
N1—S1—C1	104.09 (6)	C13—C12—C11	121.79 (16)
C17—O5—C18	116.98 (19)	C13—C12—H12	119.1
C7—N1—C14	109.15 (11)	C11—C12—H12	119.1
C7—N1—S1	128.74 (10)	C12—C13—C14	117.18 (15)
C14—N1—S1	122.06 (10)	C12—C13—H13	121.4
C6—C1—C2	121.39 (16)	C14—C13—H13	121.4
C6—C1—S1	119.23 (13)	C13—C14—C9	121.89 (13)
C2—C1—S1	119.36 (13)	C13—C14—N1	130.91 (13)
C1—C2—C3	118.37 (18)	C9—C14—N1	107.17 (12)
C1—C2—H2	120.8	C7—C15—H15A	109.5
C3—C2—H2	120.8	C7—C15—H15B	109.5
C4—C3—C2	120.57 (19)	H15A—C15—H15B	109.5
C4—C3—H3	119.7	C7—C15—H15C	109.5
C2—C3—H3	119.7	H15A—C15—H15C	109.5
C3—C4—C5	120.70 (19)	H15B—C15—H15C	109.5
C3—C4—H4	119.7	O3—C16—C8	122.50 (15)
C5—C4—H4	119.7	O3—C16—C17	116.49 (14)
C4—C5—C6	120.06 (19)	C8—C16—C17	120.47 (13)
C4—C5—H5	120.0	O4—C17—O5	126.67 (17)
C6—C5—H5	120.0	O4—C17—C16	121.70 (16)
C1—C6—C5	118.90 (17)	O5—C17—C16	111.42 (15)
C1—C6—H6	120.6	C19—C18—O5	110.8 (2)
C5—C6—H6	120.6	C19—C18—H18A	109.5
C8—C7—N1	107.63 (12)	O5—C18—H18A	109.5
C8—C7—C15	128.71 (14)	C19—C18—H18B	109.5
N1—C7—C15	123.62 (13)	O5—C18—H18B	109.5
C7—C8—C9	108.77 (12)	H18A—C18—H18B	108.1
C7—C8—C16	128.08 (13)	C18—C19—H19A	109.5
C9—C8—C16	122.96 (13)	C18—C19—H19B	109.5
C14—C9—C10	119.87 (13)	H19A—C19—H19B	109.5
C14—C9—C8	107.22 (12)	C18—C19—H19C	109.5
C10—C9—C8	132.83 (13)	H19A—C19—H19C	109.5
C11—C10—C9	118.15 (15)	H19B—C19—H19C	109.5

O1—S1—N1—C7	9.30 (15)	C16—C8—C9—C14	−173.10 (14)
O2—S1—N1—C7	138.55 (13)	C7—C8—C9—C10	178.99 (16)
C1—S1—N1—C7	−106.67 (14)	C16—C8—C9—C10	3.6 (3)
O1—S1—N1—C14	−173.50 (12)	C14—C9—C10—C11	0.0 (2)
O2—S1—N1—C14	−44.24 (14)	C8—C9—C10—C11	−176.40 (16)
C1—S1—N1—C14	70.53 (13)	C9—C10—C11—C12	0.4 (3)
O1—S1—C1—C6	−42.83 (15)	C10—C11—C12—C13	−0.3 (3)
O2—S1—C1—C6	−176.23 (13)	C11—C12—C13—C14	−0.2 (3)
N1—S1—C1—C6	71.33 (14)	C12—C13—C14—C9	0.6 (3)
O1—S1—C1—C2	135.39 (14)	C12—C13—C14—N1	178.30 (16)
O2—S1—C1—C2	1.99 (16)	C10—C9—C14—C13	−0.5 (2)
N1—S1—C1—C2	−110.45 (14)	C8—C9—C14—C13	176.71 (15)
C6—C1—C2—C3	0.3 (3)	C10—C9—C14—N1	−178.69 (13)
S1—C1—C2—C3	−177.86 (16)	C8—C9—C14—N1	−1.45 (16)
C1—C2—C3—C4	−1.2 (3)	C7—N1—C14—C13	−177.75 (16)
C2—C3—C4—C5	1.1 (4)	S1—N1—C14—C13	4.6 (2)
C3—C4—C5—C6	−0.1 (4)	C7—N1—C14—C9	0.18 (16)
C2—C1—C6—C5	0.7 (3)	S1—N1—C14—C9	−177.51 (10)
S1—C1—C6—C5	178.83 (15)	C7—C8—C16—O3	165.01 (17)
C4—C5—C6—C1	−0.8 (3)	C9—C8—C16—O3	−20.6 (3)
C14—N1—C7—C8	1.23 (16)	C7—C8—C16—C17	−23.7 (2)
S1—N1—C7—C8	178.72 (11)	C9—C8—C16—C17	150.71 (15)
C14—N1—C7—C15	−176.61 (14)	C18—O5—C17—O4	−3.1 (3)
S1—N1—C7—C15	0.9 (2)	C18—O5—C17—C16	171.70 (18)
N1—C7—C8—C9	−2.13 (16)	O3—C16—C17—O4	114.6 (2)
C15—C7—C8—C9	175.57 (15)	C8—C16—C17—O4	−57.2 (2)
N1—C7—C8—C16	172.93 (14)	O3—C16—C17—O5	−60.5 (2)
C15—C7—C8—C16	−9.4 (3)	C8—C16—C17—O5	127.69 (16)
C7—C8—C9—C14	2.26 (16)	C17—O5—C18—C19	89.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3ⁱ	0.93	2.56	3.197 (2)	126
C2—H2···O2	0.93	2.52	2.897 (2)	104
C10—H10···O3	0.93	2.51	3.026 (2)	115
C13—H13···O2	0.93	2.48	3.001 (2)	116
C15—H15B···O1	0.96	2.43	2.798 (2)	103
C3—H3···Cg1ⁱⁱ	0.93	2.70	3.524	148
C4—H4···Cg2ⁱⁱ	0.93	2.90	3.619	135

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇NO₅S
M_r	371.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	9.6696 (4), 13.1526 (5), 13.8048 (5)
β (°)	94.898 (1)
V (Å³)	1749.29 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.24 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.929, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	25430, 6064, 4222
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.746

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.161, 1.06
No. of reflections	6064
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.33

Computer programs: APEX2 (Bruker, 2004), APEX2, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3ⁱ	0.93	2.56	3.197 (2)	126
C2—H2···O2	0.93	2.52	2.897 (2)	104
C10—H10···O3	0.93	2.51	3.026 (2)	115
C13—H13···O2	0.93	2.48	3.001 (2)	116
C15—H15B···O1	0.96	2.43	2.798 (2)	103
C3—H3···Cg1ⁱⁱ	0.93	2.70	3.524	148
C4—H4···Cg2ⁱⁱ	0.93	2.90	3.619	135

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1/2, −y+1/2, z−1/2.

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