N-Methyl-N-(1-phenyl­sulfonyl­indol-2-ylmethyl)­aniline

In the title compound, 2-[(methylphenylamino)methyl]-1-(phenylsulfonyl)indole, C₂₂H₂₀N₂O₂S, the indole system is not strictly planar and the dihedral angle between the fused rings is 2.7 (1)°. The angles around the S atom of the sulfonyl substituent deviate significantly from the ideal value for tetrahedral geometry. The pyramidalization at the indole N atom is very small. Of the two C—H...O interactions, one influences the orientation of indole with respect to the sulfonyl group and the other determines the orientation of the phenyl bound to sulfonyl. The phenyl ring of the sulfonyl substituent makes a dihedral angle of 89.6 (1)° with the best plane of the indole. The molecular packing is stabilized by C—H...π and C—H...O hydrogen bonds.

S1. Comment

The biological activities of indoles and their derivatives have been known for a long time. The indole unit occurs naturally in a wide variety of structures. The indole ring system occurs in plants (Nigović et al., 2000). Indolines and their oxidized counter parts are important pharmacophores that appear in numerous biologically active compounds most notably those affecting central nervous system (Zhang & Liebeskind, 1996). Certain indole derivatives possess antidepressive (Papenstasion & Newmeyer, 1972), anti-inflammatory (Rodriguez et al., 1985; Polletto et al., 1974), antimicrobial (El-Sayed et al., 1986; Gadaginamath, 1999), antitumor (Schollmeyer et al., 1995) and antibacterial (Okabe & Adachi, 1998) activities. They have been proven to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999). Because of the wide range of biological activities of indole derivatives, we have undertaken the X-ray studies on an indole derivative, (I), in order to study its conformations in the solid state. \sch

The indole system is not strictly planar and the dihedral angle formed by the pyrrole and benzo planes is 2.7 (1)°. Atom N1 deviates by -0.104 (2) Å from the mean plane passing through S1, C1 and C4. This slight pyramidalization behaviour is also observed in related indoles (Yokum & Fronczek, 1997; Beddoes et al., 1986). The torsion angles O2—S1—N1—C4 = 152.0 (2)° and O2—S1—C9—C14 = 175.5 (2)° describe the conformation of the phenylsulfonyl group with respect to the indole system which cause the best planes of the indole and phenyl rings to form a dihedral angle of 89.6 (1)° as observed in similar structures (Yokum & Fronczek, 1997).

In the benzene ring of the indole system, endocyclic angles at C8 and C5 are contracted to 117.3 (2) and 119.2 (2)° while those at C7 and C4 are expanded to 122.4 (2) and 121.5 (2)°, respectively. This would appear to be a real effect caused by the fusion of the smaller pyrrole ring to the six-membered benzene ring. A similar effect has also been observed by Sivaraman et al. (1994a,b, 1996), Govindasamy et al. (1999) and Sankaranarayanan et al. (2000).

The phenyl ring attached to N16 is inclined to an angle of 83.1 (1)° with indole mean plane and 66.0 (1)° with the phenyl ring of the sulfonyl group. The sum of the angles around N16 [359.1 (4)°] is indicative of sp² hybridized character. The orientation of the indole substituent is influenced by a weak interaction C8—H8···O1 quantitatively defined by the torsion angles C8—C4—N1—S1 [-9.6 (3)°], C4—N1—S1—C9 [-93.6 (2)°] while the orientation of the phenyl bound to the sulfonyl group is governed by the C10—H10···O2 interaction (Table. 2) quantitatively defined by the torsion angle O2—S1—C9—C10 [-4.2 (2)°].

The angular disposition of the bonds about the S atom shows significant deviation from that of a regular tetrahedron, with the largest deviation in O—S—O angle. The widening of the angle O1—S1—O2 = 120.4 (1)° from the ideal tetrahedral value is presumably the result of the repulsive interactions between the short S═O bonds similar to that observed in related structures (Govindasamy et al., 1999; Rodriguez et al., 1985; Beddoes et al., 1986). The S—N and S—C bond distances agree well with the literature values of 1.642 (24) and 1.758 (13) Å (Allen et al., 1987), respectively.

In addition to van der Waals interactions, the molecular packing is stabilized by a C—H···O hydrogen bond and C—H···π interaction (Table 2), where Cg1 is the ring centroid of the benzene ring (C3—C8).

Related literature

For related literature, see: Allen et al. (1987); Beddoes et al. (1986); El-Sayed, Barnhart, Ammon & Wassel (1986); Gadaginamath & Patil (1999); Govindasamy et al. (1999); Nigović et al. (2000); Okabe & Adachi (1998); Papenstasion & Newmeyer (1972); Polletto et al. (1974); Rajeswaran et al. (1999); Rodriguez et al. (1985); Sankaranarayanan et al. (2000); Schollmeyer et al. (1995); Sivaraman et al. (1994a, 1994b, 1996); Yokum & Fronczek (1997); Zhang & Liebeskind (1996).

S2. Experimental

3-Bromo-(1-phenylsulfonylindol-2-yl-methyl)-N-methylaniline was treated with tetrakis(triphenylphosphine)palladium(0) in DMF at 353 K and gave the corresponding debrominated product of the title compound in 70% yield.

S3. Refinement

All the hydrogen atoms were included in calculated positions and allowed to ride on their corresponding parent atoms.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures

	Fig. 1. Molecular structure showing 50% probability displacement ellipsoids with the atom-numbering scheme.
	Fig. 2. Packing of the molecule viewed down the a axis showing C—H···π interaction.

N-(1-Phenylsulfonylindol-2-yl-methyl)-N-methylaniline

Crystal data

C22H20N2O2S	Dx = 1.311 Mg m^−3
Mr = 376.46	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 4762 reflections
a = 8.3162 (2) Å	θ = 1.6–28.3°
b = 11.2384 (3) Å	µ = 0.19 mm^−1
c = 20.4080 (5) Å	T = 293 K
V = 1907.35 (8) Å^3	Block, yellow
Z = 4	0.44 × 0.42 × 0.24 mm
F(000) = 792

Data collection

Siemens SMART CCD area detector diffractometer	3474 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Graphite monochromator	θmax = 28.3°, θmin = 2.0°
ω scans	h = −10→11
13206 measured reflections	k = −14→10
4707 independent reflections	l = −22→27

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.041	Calculated w = 1/[σ^2(Fo^2) + (0.0673P)^2 + 0.2417P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.119	(Δ/σ)max < 0.001
S = 0.91	Δρmax = 0.17 e Å^−3
4707 reflections	Δρmin = −0.19 e Å^−3
245 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0070 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.06 (8)

Special details

Experimental. Data were collected over a hemisphere of reciprocal space, by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Coverage of the unique set was over 99% complete. Crystal decay was monitored by repeating 30 initial frames at the end of data collection and analysing the duplicate reflections; it was found negligible.

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	−0.53831 (7)	−0.59191 (6)	−0.18734 (3)	0.06009 (17)
O1	−0.4736 (2)	−0.68787 (18)	−0.22452 (8)	0.0782 (5)
O2	−0.5188 (2)	−0.47274 (17)	−0.20896 (9)	0.0864 (6)
N1	−0.7355 (2)	−0.61532 (16)	−0.18227 (8)	0.0537 (4)
C1	−0.8477 (3)	−0.53331 (19)	−0.15495 (10)	0.0538 (5)
C2	−0.9893 (3)	−0.58827 (19)	−0.14875 (11)	0.0583 (5)
H2	−1.0828	−0.5537	−0.1326	0.070*
C3	−0.9748 (3)	−0.70952 (19)	−0.17101 (10)	0.0534 (5)
C4	−0.8141 (3)	−0.72642 (19)	−0.18967 (10)	0.0507 (5)
C5	−1.0820 (3)	−0.8044 (2)	−0.17505 (12)	0.0680 (6)
H5	−1.1897	−0.7940	−0.1641	0.082*
C6	−1.0267 (3)	−0.9140 (2)	−0.19547 (12)	0.0738 (6)
H6	−1.0970	−0.9782	−0.1978	0.089*
C7	−0.8671 (4)	−0.9286 (2)	−0.21244 (13)	0.0749 (7)
H7	−0.8320	−1.0034	−0.2256	0.090*
C8	−0.7583 (3)	−0.8365 (2)	−0.21058 (11)	0.0652 (6)
H8	−0.6516	−0.8475	−0.2228	0.078*
C9	−0.4707 (2)	−0.60162 (19)	−0.10583 (10)	0.0538 (5)
C10	−0.4021 (3)	−0.5042 (2)	−0.07598 (14)	0.0736 (7)
H10	−0.3902	−0.4328	−0.0986	0.088*
C11	−0.3511 (4)	−0.5146 (3)	−0.01152 (15)	0.0891 (9)
H11	−0.3016	−0.4505	0.0091	0.107*
C12	−0.3731 (4)	−0.6189 (3)	0.02193 (15)	0.0929 (10)
H12	−0.3413	−0.6242	0.0655	0.111*
C13	−0.4408 (4)	−0.7148 (3)	−0.00770 (15)	0.0892 (9)
H13	−0.4551	−0.7851	0.0156	0.107*
C14	−0.4885 (4)	−0.7080 (2)	−0.07251 (12)	0.0698 (6)
H14	−0.5320	−0.7742	−0.0934	0.084*
C15	−0.8045 (3)	−0.4069 (2)	−0.13825 (13)	0.0698 (6)
H15A	−0.7016	−0.4058	−0.1159	0.084*
H15B	−0.7937	−0.3613	−0.1784	0.084*
N16	−0.9251 (3)	−0.35120 (17)	−0.09670 (12)	0.0776 (6)
C17	−1.0245 (5)	−0.2598 (3)	−0.12489 (19)	0.1061 (11)
H17A	−1.0101	−0.2589	−0.1716	0.159*
H17B	−0.9945	−0.1840	−0.1071	0.159*
H17C	−1.1352	−0.2757	−0.1148	0.159*
C18	−0.9234 (3)	−0.37291 (19)	−0.02964 (14)	0.0637 (6)
C19	−0.8243 (3)	−0.4597 (2)	−0.00238 (13)	0.0690 (6)
H19	−0.7569	−0.5035	−0.0296	0.083*
C20	−0.8236 (4)	−0.4822 (3)	0.06377 (13)	0.0828 (8)
H20	−0.7548	−0.5398	0.0807	0.099*
C21	−0.9236 (5)	−0.4206 (3)	0.10500 (17)	0.1034 (11)
H21	−0.9251	−0.4373	0.1496	0.124*
C22	−1.0197 (5)	−0.3354 (3)	0.0797 (2)	0.1087 (12)
H22	−1.0868	−0.2927	0.1076	0.130*
C23	−1.0209 (4)	−0.3100 (2)	0.01354 (18)	0.0863 (9)
H23	−1.0876	−0.2502	−0.0023	0.104*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0502 (3)	0.0798 (4)	0.0502 (3)	−0.0021 (3)	0.0122 (2)	0.0113 (3)
O1	0.0586 (9)	0.1168 (14)	0.0592 (9)	0.0102 (10)	0.0194 (8)	−0.0119 (9)
O2	0.0836 (13)	0.0927 (12)	0.0830 (12)	−0.0124 (11)	0.0190 (10)	0.0367 (10)
N1	0.0491 (9)	0.0669 (11)	0.0451 (8)	0.0071 (8)	0.0044 (7)	0.0003 (8)
C1	0.0574 (12)	0.0523 (12)	0.0517 (11)	0.0128 (10)	0.0015 (9)	0.0084 (9)
C2	0.0531 (13)	0.0592 (12)	0.0626 (12)	0.0161 (10)	0.0083 (9)	0.0072 (10)
C3	0.0506 (10)	0.0628 (12)	0.0467 (10)	0.0080 (10)	0.0026 (9)	0.0030 (9)
C4	0.0513 (11)	0.0622 (12)	0.0386 (9)	0.0034 (9)	0.0027 (9)	−0.0013 (9)
C5	0.0534 (13)	0.0840 (17)	0.0664 (14)	−0.0033 (12)	0.0053 (11)	0.0013 (13)
C6	0.0763 (15)	0.0758 (15)	0.0692 (15)	−0.0113 (14)	−0.0004 (13)	−0.0112 (13)
C7	0.0831 (18)	0.0711 (16)	0.0705 (15)	0.0047 (14)	−0.0014 (14)	−0.0225 (12)
C8	0.0596 (14)	0.0791 (16)	0.0569 (12)	0.0120 (12)	0.0050 (10)	−0.0179 (11)
C9	0.0407 (9)	0.0643 (12)	0.0565 (11)	0.0018 (10)	0.0059 (9)	0.0000 (10)
C10	0.0617 (14)	0.0726 (16)	0.0864 (18)	−0.0103 (12)	0.0060 (13)	−0.0047 (13)
C11	0.0685 (17)	0.113 (2)	0.0856 (19)	−0.0088 (16)	−0.0093 (15)	−0.0324 (18)
C12	0.085 (2)	0.129 (3)	0.0649 (16)	0.018 (2)	−0.0157 (15)	−0.0065 (18)
C13	0.108 (2)	0.0901 (19)	0.0698 (16)	0.0154 (19)	−0.0091 (17)	0.0151 (15)
C14	0.0824 (18)	0.0636 (13)	0.0634 (13)	0.0044 (12)	−0.0062 (12)	0.0064 (11)
C15	0.0774 (16)	0.0571 (14)	0.0748 (15)	0.0051 (12)	−0.0002 (13)	0.0112 (12)
N16	0.0884 (16)	0.0535 (11)	0.0909 (16)	0.0262 (11)	−0.0047 (12)	0.0021 (10)
C17	0.117 (3)	0.0704 (17)	0.131 (3)	0.0382 (18)	−0.035 (2)	0.0006 (18)
C18	0.0622 (14)	0.0440 (11)	0.0851 (16)	−0.0007 (10)	0.0026 (11)	−0.0121 (10)
C19	0.0747 (16)	0.0616 (13)	0.0706 (14)	0.0103 (12)	0.0030 (13)	−0.0064 (12)
C20	0.100 (2)	0.0768 (17)	0.0712 (16)	−0.0009 (16)	−0.0046 (16)	−0.0026 (14)
C21	0.134 (3)	0.097 (2)	0.0794 (19)	−0.014 (2)	0.023 (2)	−0.0246 (18)
C22	0.120 (3)	0.089 (2)	0.117 (3)	0.000 (2)	0.045 (2)	−0.040 (2)
C23	0.0768 (17)	0.0580 (14)	0.124 (3)	0.0031 (13)	0.0109 (18)	−0.0210 (15)

Geometric parameters (Å, º)

S1—O1	1.424 (2)	C11—H11	0.9300
S1—O2	1.419 (2)	C12—C13	1.358 (5)
S1—N1	1.664 (2)	C12—H12	0.9300
S1—C9	1.759 (2)	C13—C14	1.383 (4)
N1—C4	1.417 (3)	C13—H13	0.9300
N1—C1	1.425 (3)	C14—H14	0.9300
C1—C2	1.335 (3)	C15—N16	1.454 (3)
C1—C15	1.505 (3)	C15—H15A	0.9700
C2—C3	1.441 (3)	C15—H15B	0.9700
C2—H2	0.9300	N16—C18	1.390 (4)
C3—C5	1.393 (3)	N16—C17	1.438 (3)
C3—C4	1.402 (3)	C17—H17A	0.9600
C4—C8	1.389 (3)	C17—H17B	0.9600
C5—C6	1.379 (3)	C17—H17C	0.9600
C5—H5	0.9300	C18—C23	1.390 (4)
C6—C7	1.381 (4)	C18—C19	1.393 (4)
C6—H6	0.9300	C19—C20	1.374 (4)
C7—C8	1.375 (4)	C19—H19	0.9300
C7—H7	0.9300	C20—C21	1.370 (4)
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.377 (3)	C21—C22	1.350 (5)
C9—C14	1.384 (3)	C21—H21	0.9300
C10—C11	1.387 (4)	C22—C23	1.380 (5)
C10—H10	0.9300	C22—H22	0.9300
C11—C12	1.369 (4)	C23—H23	0.9300
O1—S1—O2	120.4 (1)	C13—C12—C11	120.9 (3)
O1—S1—N1	106.6 (1)	C13—C12—H12	119.6
O2—S1—N1	106.3 (1)	C11—C12—H12	119.6
O1—S1—C9	109.6 (1)	C12—C13—C14	120.1 (3)
O2—S1—C9	108.4 (1)	C12—C13—H13	119.9
N1—S1—C9	104.3 (1)	C14—C13—H13	119.9
C4—N1—C1	108.0 (2)	C13—C14—C9	119.1 (3)
C4—N1—S1	125.9 (1)	C13—C14—H14	120.4
C1—N1—S1	124.6 (2)	C9—C14—H14	120.4
C2—C1—N1	108.4 (2)	N16—C15—C1	112.0 (2)
C2—C1—C15	128.7 (2)	N16—C15—H15A	109.2
N1—C1—C15	122.9 (2)	C1—C15—H15A	109.2
C1—C2—C3	109.5 (2)	N16—C15—H15B	109.2
C1—C2—H2	125.3	C1—C15—H15B	109.2
C3—C2—H2	125.3	H15A—C15—H15B	107.9
C5—C3—C4	119.4 (2)	C18—N16—C17	121.7 (2)
C5—C3—C2	133.6 (2)	C18—N16—C15	119.4 (2)
C4—C3—C2	107.1 (2)	C17—N16—C15	118.0 (3)
C8—C4—C3	121.5 (2)	N16—C17—H17A	109.5
C8—C4—N1	131.6 (2)	N16—C17—H17B	109.5
C3—C4—N1	106.9 (2)	H17A—C17—H17B	109.5
C6—C5—C3	119.2 (2)	N16—C17—H17C	109.5
C6—C5—H5	120.4	H17A—C17—H17C	109.5
C3—C5—H5	120.4	H17B—C17—H17C	109.5
C5—C6—C7	120.2 (2)	N16—C18—C23	121.9 (3)
C5—C6—H6	119.9	N16—C18—C19	121.5 (2)
C7—C6—H6	119.9	C23—C18—C19	116.6 (3)
C8—C7—C6	122.4 (2)	C20—C19—C18	121.6 (3)
C8—C7—H7	118.8	C20—C19—H19	119.2
C6—C7—H7	118.8	C18—C19—H19	119.2
C7—C8—C4	117.3 (2)	C19—C20—C21	120.5 (3)
C7—C8—H8	121.4	C19—C20—H20	119.7
C4—C8—H8	121.4	C21—C20—H20	119.7
C10—C9—C14	121.0 (2)	C22—C21—C20	118.9 (3)
C10—C9—S1	120.1 (2)	C22—C21—H21	120.6
C14—C9—S1	119.0 (2)	C20—C21—H21	120.6
C9—C10—C11	118.6 (3)	C21—C22—C23	121.7 (3)
C9—C10—H10	120.7	C21—C22—H22	119.2
C11—C10—H10	120.7	C23—C22—H22	119.2
C12—C11—C10	120.3 (3)	C22—C23—C18	120.7 (3)
C12—C11—H11	119.9	C22—C23—H23	119.6
C10—C11—H11	119.9	C18—C23—H23	119.6
O1—S1—N1—C4	22.4 (2)	O2—S1—C9—C10	−4.2 (2)
O2—S1—N1—C4	152.0 (2)	N1—S1—C9—C10	−117.2 (2)
C9—S1—N1—C4	−93.6 (2)	O1—S1—C9—C14	−51.3 (2)
O1—S1—N1—C1	−173.1 (2)	O2—S1—C9—C14	175.5 (2)
O2—S1—N1—C1	−43.5 (2)	N1—S1—C9—C14	62.5 (2)
C9—S1—N1—C1	71.0 (2)	C14—C9—C10—C11	−0.1 (4)
C4—N1—C1—C2	−2.8 (2)	S1—C9—C10—C11	179.6 (2)
S1—N1—C1—C2	−169.7 (2)	C9—C10—C11—C12	−1.8 (4)
C4—N1—C1—C15	178.0 (2)	C10—C11—C12—C13	1.9 (5)
S1—N1—C1—C15	11.1 (3)	C11—C12—C13—C14	0.0 (5)
N1—C1—C2—C3	0.8 (2)	C12—C13—C14—C9	−1.9 (5)
C15—C1—C2—C3	179.9 (2)	C10—C9—C14—C13	2.0 (4)
C1—C2—C3—C5	179.6 (2)	S1—C9—C14—C13	−177.7 (2)
C1—C2—C3—C4	1.5 (2)	C2—C1—C15—N16	15.4 (3)
C5—C3—C4—C8	−1.6 (3)	N1—C1—C15—N16	−165.7 (2)
C2—C3—C4—C8	176.8 (2)	C1—C15—N16—C18	81.2 (3)
C5—C3—C4—N1	178.4 (2)	C1—C15—N16—C17	−109.3 (3)
C2—C3—C4—N1	−3.2 (2)	C17—N16—C18—C23	1.9 (4)
C1—N1—C4—C8	−176.3 (2)	C15—N16—C18—C23	171.0 (2)
S1—N1—C4—C8	−9.6 (3)	C17—N16—C18—C19	−178.6 (3)
C1—N1—C4—C3	3.7 (2)	C15—N16—C18—C19	−9.4 (4)
S1—N1—C4—C3	170.4 (2)	N16—C18—C19—C20	−179.3 (3)
C4—C3—C5—C6	1.9 (3)	C23—C18—C19—C20	0.3 (4)
C2—C3—C5—C6	−176.0 (2)	C18—C19—C20—C21	1.1 (5)
C3—C5—C6—C7	−0.8 (4)	C19—C20—C21—C22	−1.6 (5)
C5—C6—C7—C8	−0.7 (4)	C20—C21—C22—C23	0.8 (6)
C6—C7—C8—C4	1.0 (4)	C21—C22—C23—C18	0.7 (5)
C3—C4—C8—C7	0.2 (3)	N16—C18—C23—C22	178.4 (3)
N1—C4—C8—C7	−179.8 (2)	C19—C18—C23—C22	−1.2 (4)
O1—S1—C9—C10	129.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.93	2.33	2.911 (3)	121
C10—H10···O2	0.93	2.53	2.904 (3)	104
C8—H8···O2^i	0.93	2.43	3.217 (3)	142
C12—H12···Cg1^ii	0.93	2.75	3.568 (5)	148

Symmetry codes: (i) −x−1, y−1/2, −z−1/2; (ii) x+1/2, −y−3/2, −z.