Trimethyl[3-methyl-1-(o-tolenesulfonyl)indol-2-ylmethyl]ammonium iodide and benzyl[3-bromo-1-(phenylsulfonyl)indol-2-ylmethyl]tolylamine

The title compounds, C₂₀H₂₅N₂O₂S⁺·I^-, (I), and C₂₉H₂₅BrN₂O₂S, (II), respectively, both crystallize in space group P. The pyrrole ring subtends an angle with the sulfonyl group of 33.6° in (I) and 21.5° in (II). The phenyl ring of the sulfonyl substituent makes a dihedral angle with the best plane of the indole moiety of 81.6° in (I) and 67.2° in (II). The lengthening or shortening of the C-N bond distances in both compounds is due to the electron-withdrawing character of the phenyl­sulfonyl group. The S atoms are in distorted tetrahedral configurations. The molecular structures are stabilized by C-H...O and C-H...I interactions in (I), and by C-H...O and C-H...N interactions in (II).

S1. Comment

Indoles are known for their important chemical, medicinal and physiological activities. They are of biological interest as antitumour-active substances. Structural studies of some derivatives of indole have been useful in understanding the molecular mechanisms controlling anxiety, convulsions, memory, learning and sleep in animals. Indoles have been of interest for many years, since a large number of natural products contain these heterocyclic nuclei, and they are found in a number of pharmaceutical products, fragrances and dyes (Padwa et al., 1999). Most of them are found to possess antimicrobial, anti-inflammatory (El-Sayed et al., 1986) and muscle relaxant properties. A variety of [b]annellated indoles are of biological interest as antitumour-active substances (Schollmeyer et al., 1995). Spiro indole derivatives exhibit antibacterial and antifungal properties (Sehgal et al., 1994). Against this background and in order to obtain detailed information on molecular conformation in the solid state, X-ray studies of the title compounds, (I) and (II), have been carried out and the results are presented here. \sch

Figs. 1 and 2 show the molecules of (I) and (II) with their atomic numbering schemes. The two compounds are discussed in parallel below, for ease of comparison. Selected geometric parameters are given in Tables 1 and 3.

The indole ring system is not strictly planar. The angular disposition of the bonds about the S atom shows significant deviation from that of a regular tetrahedron, with the largest deviations being in the O—S—O [O2—S—O1 119.69 (14)° in (I) and 120.5 (2)° in (II)] and O—S—N angles [O1—S—N1 106.57 (11)° in (I) and 107.4 (2)° in (II)]. This widening of the angles may be due to repulsive interactions between the two short S═O bonds, similar to what is observed in related structures (Rodriguez et al., 1995).

The S—N bond distances [S—N1 1.665 (9) Å in (I) and 1.677 (4) Å in (II)] lie within the expected range of 1.63–1.69 Å (Kálmán et al., 1981). The average S—O, S—C, and S—N distances are 1.435, 1.776 and 1.674 Å, respectively, in (I), and 1.409, 1.746 and 1.676 Å, respectively, in (II); these are comparable with the values found in N-phenylsulfonamides (Gomes et al., 1993). The narrowing of the N1—S—C1 angle to 106.32 (11)° in (I), and of N1—S—C9 to 106.3 (2) in (II), from the ideal tetrahedral value is attributed to the Thorpe-Ingold effect (Bassindale, 1984).

The O1—S—N1—C10 and O1—S—C1—C6 torsion angles in (I), and the O1—S—N1—C1 and O1—S—C9—C10 torsion angles in (II), describe the conformation of phenylsulfonyl group with respect to the indole system, and the best planes of the indole and phenyl rings form dihedral angles of 81.6° in (I) and 67.2° in (II), as observed in similar structures (Sankaranarayanan et al., 2000).

The difference in C—N bond lengths may be due to the electron-withdrawing character of the phenylsulfonyl group (Govindasamy et al., 1998). The angular distortion of the benzene ring of the indole moiety is a characteristic property. The substitution of the phenylsulfonyl group at N1 results in an enhancement of the C—N bond lengths. The sum of the angles around N1 is 360° for (I) and 359.7° for (II), indicating sp² hybridization.

The positions of the methyl atom C16 on C14 in (I), and of the Br atom on C2 in (II), do not deviate significantly from the least-squares planes through the pyrrole ring. The average value of the bond lengths of all the six-membered rings is 1.391 Å, but there are significant deviations among the individual values. In (I), the angles at C8 and C11 are 118.3 and 116.7°, respectively, and around C13 and C10 they are 121.3 and 122.5°, respectively. In (II), the angles around C8 and C5 are 120.4 and 121.1°, respectively, and around C7 and C4 they are 116.8 and 118.0°, respectively. This may be due to the fusion of the pyrrole ring to the six-membered benzene ring.

The C14—C16 bond length of 1.499 (3) Å in (I), and the C2—Br bond length of 1.873 (4) Å in (II), are comparable with values found in the literature (Allen et al., 1987). The strain is due to angular distortion rather than bond-length distortion. A similar effect has also been observed by Sankaranarayanan et al. (2000). The dihedral angles between the pyrrole and benzene rings are 1.79° in (I) and 2.18° in (II).

The orientation of the indole substituent is influenced by a weak C11—H11···O1 interaction in (I), defined by the C11—C10—N1—S torsion angle, and a C7—H7···O2 interaction in (II), defined by the C7—C8—N1—S torsion angle, while the orientation of the phenyl ring bound to the sulfonyl group is governed by a C6—H6···O1 interaction in (I), defined by the O1—S—C1—C6 torsion angle, and by a C14—H14···O2 interaction in (II), defined by the O2—S—C9—C14 torsion angle. In addition to van der Waals interactions, the packing of the molecules in the unit cell is governed by C—H···O and C—H···I interactions in (I), and C—H···O and C—H···N interactions in (II). Details of these interactions are given in Tables 2 and 4.

S2. Experimental

The preparation of compound (I) was carried out as follows. To a solution of 1-phenylsulfonyl-3-methyl-2-(N,N-dimethylamino)methylindole (1.64 g, 5 mmol) in dry tetrahydrofuran (50 ml) under nitrogen, n-BuLi (6.25 ml, 1.6M in hexane, 5 mmol) and trimethylethylenediamine (0.2 ml) were added, and the mixture was stirred at 195 K for 30 min. To the cherry-red reaction mixture, methyl iodide (0.95 ml, 15 mmol) was added. After stirring at 195 K for 2 h, the reaction mixture was slowly heated to room temperature, and after 1 h, it was quenched with a saturated solution of NH₄Cl (20 ml). It was then extracted with dichloromethane (3 × 50 ml) and dried (MgSO₄). Removal of the solvent followed by column chromatographic purification [silica gel, ethyl acetate-hexane (1:9)] afforded the pure quaternary salt, (I). The preparation of compound (II) was carried out as follows. A solution of 1-phenylsulfonyl-2-bromomethyl-3-bromo-indole (4.29 g, 10 mmol) and N-benzyl-p-toludine (2 equivalents) in dry dimethylformamide (25 ml) containing finely powdered K₂CO₃ (200 mg) was stirred at room temperature for 12 h. The reaction mixture was then poured onto ice (200 g) and the solid which formed was filtered and washed with an excess of water. The crude product was dried over CaCl₂ and recrystallized from ethyl acetate-hexane(1:9) to give compound (II).

S3. Refinement

In both compounds, all H atoms were fixed geometrically and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for other H atoms.

Computing details

Data collection: SMART (Siemens, 1996) for (I); CAD-4 Software (Enraf-Nonius, 1989) for (II). Cell refinement: SAINT (Siemens, 1996) for (I); CAD-4 Software for (II). Data reduction: SAINT for (I); CAD-4 Software for (II). For both compounds, program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures

	Fig. 1. A view of the molecule of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity.
	Fig. 2. A view of the molecule of (II) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity.

(I) Trimethyl[3-methyl-1-(o-tolenesulfonyl)indol-2-ylmethyl]ammonium iodide

Crystal data

C20H25N2O2S^+·I^−	Z = 2
Mr = 484.38	F(000) = 488
Triclinic, P1	Dx = 1.520 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0259 (1) Å	Cell parameters from 4122 reflections
b = 12.2874 (2) Å	θ = 1.6–28.2°
c = 13.0484 (3) Å	µ = 1.63 mm^−1
α = 80.316 (1)°	T = 293 K
β = 79.508 (1)°	Block, yellow
γ = 74.462 (1)°	0.48 × 0.42 × 0.40 mm
V = 1058.64 (3) Å^3

Data collection

Siemens SMART CCD area-detector diffractometer	5062 independent reflections
Radiation source: fine-focus sealed tube	4494 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω scans	θmax = 28.2°, θmin = 1.6°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −9→6
Tmin = 0.472, Tmax = 0.522	k = −16→16
7395 measured reflections	l = −16→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.052P)^2 + 0.0768P] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.002
5062 reflections	Δρmax = 0.84 e Å^−3
226 parameters	Δρmin = −0.55 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0213 (13)

Special details

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
I1	−0.15238 (2)	0.514750 (14)	0.782778 (12)	0.04768 (9)
S	0.19305 (9)	0.06052 (5)	0.85595 (4)	0.03867 (13)
N1	0.2278 (3)	0.17371 (15)	0.77157 (14)	0.0354 (4)
N2	0.3992 (3)	0.30834 (17)	0.93723 (15)	0.0391 (4)
O1	−0.0154 (3)	0.08328 (18)	0.89554 (16)	0.0560 (5)
O2	0.3355 (3)	0.03789 (15)	0.92727 (15)	0.0544 (5)
C1	0.2534 (4)	−0.05538 (18)	0.7812 (2)	0.0429 (5)
C2	0.4368 (5)	−0.0870 (2)	0.7178 (3)	0.0581 (7)
C3	0.4711 (6)	−0.1877 (3)	0.6745 (4)	0.0809 (11)
H3	0.5913	−0.2121	0.6316	0.097*
C4	0.3332 (8)	−0.2525 (3)	0.6932 (4)	0.0868 (13)
H4	0.3629	−0.3199	0.6636	0.104*
C5	0.1542 (6)	−0.2194 (3)	0.7541 (4)	0.0769 (11)
H5	0.0608	−0.2629	0.7648	0.092*
C6	0.1125 (5)	−0.1202 (3)	0.8000 (4)	0.0574 (7)
H6	−0.0082	−0.0971	0.8429	0.069*
C7	0.5923 (5)	−0.0201 (3)	0.6968 (4)	0.0925 (14)
H7A	0.7122	−0.0623	0.6589	0.139*
H7B	0.6202	−0.0065	0.7622	0.139*
H7C	0.5444	0.0514	0.6556	0.139*
C8	0.1425 (6)	0.3416 (3)	0.5229 (4)	0.0451 (5)
H8	0.1902	0.4008	0.4817	0.054*
C9	0.2110 (2)	0.2931 (1)	0.6188 (1)	0.0358 (4)
C10	0.1336 (5)	0.2052 (3)	0.6802 (3)	0.0350 (4)
C11	−0.0100 (4)	0.1631 (2)	0.6496 (2)	0.0470 (5)
H11	−0.0625	0.1060	0.6917	0.056*
C12	−0.0709 (5)	0.2106 (3)	0.5528 (2)	0.0557 (7)
H12	−0.1628	0.1827	0.5285	0.067*
C13	0.0024 (5)	0.2991 (3)	0.4912 (2)	0.0539 (7)
H13	−0.0440	0.3301	0.4277	0.065*
C14	0.3526 (3)	0.31675 (18)	0.67330 (17)	0.0360 (4)
C15	0.3631 (3)	0.24486 (17)	0.76521 (16)	0.0329 (4)
C16	0.4601 (5)	0.4091 (2)	0.6336 (2)	0.0514 (6)
H16A	0.3674	0.4820	0.6382	0.077*
H16B	0.5188	0.4029	0.5617	0.077*
H16C	0.5631	0.4016	0.6755	0.077*
C17	0.4935 (3)	0.23823 (19)	0.84584 (18)	0.0376 (4)
H17A	0.6117	0.2629	0.8108	0.045*
H17B	0.5368	0.1591	0.8748	0.045*
C18	0.5555 (5)	0.2868 (3)	1.0086 (2)	0.0631 (8)
H18A	0.5050	0.3323	1.0652	0.095*
H18B	0.6736	0.3068	0.9694	0.095*
H18C	0.5874	0.2078	1.0366	0.095*
C19	0.3450 (4)	0.4333 (2)	0.8993 (2)	0.0457 (5)
H19A	0.2501	0.4481	0.8511	0.069*
H19B	0.4627	0.4568	0.8643	0.069*
H19C	0.2874	0.4749	0.9580	0.069*
C20	0.2141 (5)	0.2773 (3)	0.9968 (2)	0.0643 (8)
H20A	0.2456	0.1982	1.0251	0.096*
H20B	0.1164	0.2906	0.9505	0.096*
H20C	0.1617	0.3230	1.0532	0.096*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.04048 (11)	0.05981 (13)	0.04467 (12)	−0.01184 (7)	−0.00632 (7)	−0.01245 (7)
S	0.0486 (3)	0.0345 (2)	0.0357 (3)	−0.0166 (2)	−0.0111 (2)	0.0040 (2)
N1	0.0438 (10)	0.0324 (8)	0.0330 (9)	−0.0150 (7)	−0.0118 (7)	0.0032 (7)
N2	0.0462 (10)	0.0428 (10)	0.0331 (9)	−0.0166 (8)	−0.0088 (8)	−0.0058 (8)
O1	0.0562 (11)	0.0584 (11)	0.0497 (11)	−0.0221 (9)	0.0050 (8)	0.0031 (8)
O2	0.0790 (14)	0.0455 (9)	0.0474 (10)	−0.0241 (9)	−0.0320 (10)	0.0096 (8)
C1	0.0503 (13)	0.0311 (10)	0.0517 (13)	−0.0123 (9)	−0.0219 (11)	0.0021 (9)
C2	0.0513 (15)	0.0435 (13)	0.082 (2)	−0.0032 (11)	−0.0204 (14)	−0.0167 (13)
C3	0.075 (2)	0.0593 (18)	0.110 (3)	0.0022 (17)	−0.021 (2)	−0.037 (2)
C4	0.120 (4)	0.0453 (16)	0.110 (3)	−0.0114 (19)	−0.051 (3)	−0.0273 (19)
C5	0.108 (3)	0.0540 (17)	0.090 (3)	−0.0414 (19)	−0.041 (2)	−0.0020 (17)
C6	0.0715 (18)	0.0483 (14)	0.0633 (17)	−0.0322 (13)	−0.0222 (14)	0.0047 (12)
C7	0.0457 (17)	0.086 (2)	0.149 (4)	−0.0172 (17)	0.016 (2)	−0.055 (3)
C8	0.0566 (14)	0.0438 (12)	0.0312 (11)	−0.0081 (11)	−0.0082 (10)	0.0003 (9)
C9	0.0426 (11)	0.0318 (9)	0.0307 (10)	−0.0068 (8)	−0.0017 (8)	−0.0051 (8)
C10	0.0401 (11)	0.0343 (9)	0.0309 (10)	−0.0091 (8)	−0.0084 (8)	−0.0015 (8)
C11	0.0487 (13)	0.0476 (13)	0.0491 (14)	−0.0173 (11)	−0.0175 (11)	0.0022 (10)
C12	0.0548 (15)	0.0645 (16)	0.0550 (16)	−0.0158 (13)	−0.0264 (13)	−0.0059 (13)
C13	0.0593 (16)	0.0618 (16)	0.0395 (13)	−0.0085 (13)	−0.0197 (12)	0.0003 (11)
C14	0.0437 (11)	0.0322 (9)	0.0325 (10)	−0.0118 (8)	−0.0017 (8)	−0.0050 (8)
C15	0.0376 (10)	0.0313 (9)	0.0319 (10)	−0.0117 (8)	−0.0041 (8)	−0.0053 (8)
C16	0.0652 (16)	0.0479 (13)	0.0461 (14)	−0.0298 (12)	−0.0054 (12)	0.0029 (11)
C17	0.0396 (11)	0.0385 (10)	0.0372 (11)	−0.0103 (9)	−0.0073 (9)	−0.0088 (9)
C18	0.076 (2)	0.0657 (17)	0.0529 (16)	−0.0035 (15)	−0.0382 (15)	−0.0126 (13)
C19	0.0505 (13)	0.0397 (11)	0.0501 (14)	−0.0112 (10)	−0.0120 (11)	−0.0088 (10)
C20	0.077 (2)	0.0757 (19)	0.0499 (15)	−0.0452 (17)	0.0200 (14)	−0.0232 (14)

Geometric parameters (Å, º)

S—O1	1.429 (2)	C8—H8	0.9300
S—O2	1.4311 (18)	C9—C10	1.403 (4)
S—N1	1.6659 (18)	C9—C14	1.437 (3)
S—C1	1.775 (2)	C10—C11	1.393 (3)
N1—C10	1.416 (2)	C11—C12	1.390 (4)
N1—C15	1.438 (3)	C11—H11	0.9300
N2—C20	1.496 (3)	C12—C13	1.396 (4)
N2—C19	1.499 (3)	C12—H12	0.9300
N2—C18	1.509 (3)	C13—H13	0.9300
N2—C17	1.535 (3)	C14—C15	1.366 (3)
C1—C6	1.394 (3)	C14—C16	1.499 (3)
C1—C2	1.395 (4)	C15—C17	1.495 (3)
C2—C3	1.391 (4)	C16—H16A	0.9600
C2—C7	1.497 (3)	C16—H16B	0.9600
C3—C4	1.376 (6)	C16—H16C	0.9600
C3—H3	0.9300	C17—H17A	0.9700
C4—C5	1.360 (5)	C17—H17B	0.9700
C4—H4	0.9300	C18—H18A	0.9600
C5—C6	1.386 (6)	C18—H18B	0.9600
C5—H5	0.9300	C18—H18C	0.9600
C6—H6	0.9300	C19—H19A	0.9600
C7—H7A	0.9600	C19—H19B	0.9600
C7—H7B	0.9600	C19—H19C	0.9600
C7—H7C	0.9600	C20—H20A	0.9600
C8—C13	1.381 (3)	C20—H20B	0.9600
C8—C9	1.403 (5)	C20—H20C	0.9600
O1—S—O2	119.69 (14)	C9—C10—N1	107.2 (3)
O1—S—N1	106.57 (11)	C12—C11—C10	116.7 (2)
O2—S—N1	107.13 (10)	C12—C11—H11	121.7
O1—S—C1	108.44 (13)	C10—C11—H11	121.7
O2—S—C1	107.96 (11)	C11—C12—C13	121.7 (3)
N1—S—C1	106.32 (11)	C11—C12—H12	119.2
C10—N1—C15	107.92 (15)	C13—C12—H12	119.2
C10—N1—S	120.47 (13)	C8—C13—C12	121.3 (2)
C15—N1—S	131.13 (15)	C8—C13—H13	119.4
C20—N2—C19	107.5 (2)	C12—C13—H13	119.4
C20—N2—C18	110.3 (2)	C15—C14—C9	108.42 (18)
C19—N2—C18	108.2 (2)	C15—C14—C16	128.0 (2)
C20—N2—C17	112.73 (19)	C9—C14—C16	123.54 (19)
C19—N2—C17	111.33 (18)	C14—C15—N1	108.23 (18)
C18—N2—C17	106.7 (2)	C14—C15—C17	126.9 (2)
C6—C1—C2	122.3 (2)	N1—C15—C17	124.91 (19)
C6—C1—S	114.56 (18)	C14—C16—H16A	109.5
C2—C1—S	122.7 (2)	C14—C16—H16B	109.5
C3—C2—C1	115.9 (3)	H16A—C16—H16B	109.5
C3—C2—C7	120.4 (3)	C14—C16—H16C	109.5
C1—C2—C7	123.8 (2)	H16A—C16—H16C	109.5
C4—C3—C2	122.2 (4)	H16B—C16—H16C	109.5
C4—C3—H3	118.9	C15—C17—N2	116.17 (18)
C2—C3—H3	118.9	C15—C17—H17A	108.2
C5—C4—C3	121.1 (3)	N2—C17—H17A	108.2
C5—C4—H4	119.5	C15—C17—H17B	108.2
C3—C4—H4	119.5	N2—C17—H17B	108.2
C4—C5—C6	119.3 (4)	H17A—C17—H17B	107.4
C4—C5—H5	120.4	N2—C18—H18A	109.5
C6—C5—H5	120.4	N2—C18—H18B	109.5
C5—C6—C1	119.3 (4)	H18A—C18—H18B	109.5
C5—C6—H6	120.3	N2—C18—H18C	109.5
C1—C6—H6	120.3	H18A—C18—H18C	109.5
C2—C7—H7A	109.5	H18B—C18—H18C	109.5
C2—C7—H7B	109.5	N2—C19—H19A	109.5
H7A—C7—H7B	109.5	N2—C19—H19B	109.5
C2—C7—H7C	109.5	H19A—C19—H19B	109.5
H7A—C7—H7C	109.5	N2—C19—H19C	109.5
H7B—C7—H7C	109.5	H19A—C19—H19C	109.5
C13—C8—C9	118.3 (3)	H19B—C19—H19C	109.5
C13—C8—H8	120.9	N2—C20—H20A	109.5
C9—C8—H8	120.9	N2—C20—H20B	109.5
C8—C9—C10	119.5 (3)	H20A—C20—H20B	109.5
C8—C9—C14	132.18 (10)	N2—C20—H20C	109.5
C10—C9—C14	108.25 (10)	H20A—C20—H20C	109.5
C11—C10—C9	122.5 (3)	H20B—C20—H20C	109.5
C11—C10—N1	130.34 (15)
O1—S—N1—C10	−61.93 (18)	C14—C9—C10—N1	−0.6 (3)
O2—S—N1—C10	168.84 (16)	C15—N1—C10—C11	−179.3 (2)
C1—S—N1—C10	53.60 (18)	S—N1—C10—C11	7.7 (3)
O1—S—N1—C15	127.0 (2)	C15—N1—C10—C9	0.51 (16)
O2—S—N1—C15	−2.2 (2)	S—N1—C10—C9	−172.42 (10)
C1—S—N1—C15	−117.5 (2)	C9—C10—C11—C12	1.5 (3)
O1—S—C1—C6	−17.68 (19)	N1—C10—C11—C12	−178.6 (2)
O2—S—C1—C6	113.38 (16)	C10—C11—C12—C13	−2.4 (4)
N1—S—C1—C6	−131.95 (15)	C9—C8—C13—C12	0.3 (3)
O1—S—C1—C2	169.2 (2)	C11—C12—C13—C8	1.5 (5)
O2—S—C1—C2	−59.7 (2)	C8—C9—C14—C15	179.4 (3)
N1—S—C1—C2	55.0 (2)	C10—C9—C14—C15	0.46 (18)
C6—C1—C2—C3	−0.2 (4)	C8—C9—C14—C16	1.4 (3)
S—C1—C2—C3	172.3 (2)	C10—C9—C14—C16	−177.46 (19)
C6—C1—C2—C7	−179.4 (2)	C9—C14—C15—N1	−0.1 (2)
S—C1—C2—C7	−6.8 (4)	C16—C14—C15—N1	177.7 (2)
C1—C2—C3—C4	−0.1 (5)	C9—C14—C15—C17	179.01 (19)
C7—C2—C3—C4	179.1 (3)	C16—C14—C15—C17	−3.2 (4)
C2—C3—C4—C5	1.0 (6)	C10—N1—C15—C14	−0.2 (2)
C3—C4—C5—C6	−1.6 (4)	S—N1—C15—C14	171.68 (17)
C4—C5—C6—C1	1.2 (7)	C10—N1—C15—C17	−179.40 (18)
C2—C1—C6—C5	−0.3 (3)	S—N1—C15—C17	−7.5 (3)
S—C1—C6—C5	−173.4 (3)	C14—C15—C17—N2	94.1 (3)
C13—C8—C9—C10	−1.2 (5)	N1—C15—C17—N2	−86.9 (3)
C13—C8—C9—C14	−179.9 (2)	C20—N2—C17—C15	57.8 (3)
C8—C9—C10—C11	0.2 (4)	C19—N2—C17—C15	−63.1 (3)
C14—C9—C10—C11	179.3 (2)	C18—N2—C17—C15	179.0 (2)
C8—C9—C10—N1	−179.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···I1	0.96	2.98	3.882 (3)	157
C20—H20A···O2	0.96	2.41	3.078 (4)	127
C17—H17B···O2	0.97	2.26	2.928 (3)	125
C6—H6···O1	0.93	2.41	2.837 (2)	108
C11—H11···O1	0.93	2.69	3.191 (3)	114

(II) Benzyl[3-bromo-1-(phenylsulfonyl)indol-2-ylmethyl]tolylamine

Crystal data

C29H25BrN2O2S	Z = 2
Mr = 545.48	F(000) = 560
Triclinic, P1	Dx = 1.471 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 9.742 (5) Å	Cell parameters from 25 reflections
b = 12.211 (5) Å	θ = 1.9–25.0°
c = 12.446 (5) Å	µ = 1.78 mm^−1
α = 61.362 (5)°	T = 293 K
β = 99.119 (5)°	Block, yellow
γ = 108.610 (5)°	0.48 × 0.34 × 0.28 mm
V = 1231.5 (10) Å^3

Data collection

Enraf-Nonius CAD-4 diffractometer	2645 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
ω scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = −14→13
Tmin = 0.481, Tmax = 0.635	l = −14→14
4619 measured reflections	3 standard reflections every 120 min
4340 independent reflections	intensity decay: <2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H-atom parameters constrained
S = 0.89	w = 1/[σ^2(Fo^2) + (0.052P)^2 + 0.0768P] where P = (Fo^2 + 2Fc^2)/3
4340 reflections	(Δ/σ)max = 0.007
317 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

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
Br	0.62726 (6)	0.72945 (5)	0.20377 (5)	0.0632 (2)
S	0.24246 (14)	0.64916 (11)	0.54329 (12)	0.0567 (3)
O1	0.1236 (4)	0.6136 (3)	0.4735 (4)	0.0727 (10)
O2	0.2565 (4)	0.5640 (3)	0.6693 (3)	0.0790 (11)
N1	0.3940 (4)	0.6731 (3)	0.4776 (3)	0.0486 (9)
N2	0.2357 (4)	0.8348 (3)	0.2337 (4)	0.0534 (10)
C1	0.4108 (5)	0.7055 (4)	0.3537 (4)	0.0449 (11)
C2	0.5445 (5)	0.6996 (4)	0.3447 (4)	0.0443 (10)
C3	0.6186 (5)	0.6654 (4)	0.4591 (4)	0.0456 (11)
C4	0.7565 (5)	0.6485 (4)	0.4965 (4)	0.0537 (12)
H4	0.8188	0.6561	0.4423	0.064*
C5	0.7969 (6)	0.6205 (5)	0.6146 (5)	0.0663 (14)
H5	0.8884	0.6092	0.6414	0.080*
C6	0.7047 (7)	0.6085 (5)	0.6949 (5)	0.0719 (15)
H6	0.7366	0.5908	0.7745	0.086*
C7	0.5661 (6)	0.6218 (4)	0.6620 (5)	0.0646 (14)
H7	0.5043	0.6119	0.7177	0.078*
C8	0.5236 (5)	0.6506 (4)	0.5409 (4)	0.0485 (11)
C9	0.2488 (5)	0.7989 (4)	0.5319 (4)	0.0493 (11)
C10	0.1484 (6)	0.8605 (5)	0.4619 (5)	0.0677 (14)
H10	0.0803	0.8251	0.4173	0.081*
C11	0.1481 (7)	0.9755 (6)	0.4574 (5)	0.0824 (17)
H11	0.0799	1.0180	0.4094	0.099*
C12	0.2474 (7)	1.0269 (5)	0.5229 (5)	0.0773 (17)
H12	0.2464	1.1041	0.5201	0.093*
C13	0.3472 (7)	0.9665 (5)	0.5920 (5)	0.0807 (17)
H13	0.4150	1.0027	0.6361	0.097*
C14	0.3501 (6)	0.8513 (5)	0.5980 (5)	0.0706 (15)
H14	0.4192	0.8097	0.6457	0.085*
C15	0.2963 (5)	0.7299 (4)	0.2567 (4)	0.0542 (12)
H15A	0.3366	0.7498	0.1809	0.065*
H15B	0.2178	0.6502	0.2794	0.065*
C16	0.0842 (5)	0.8115 (5)	0.1920 (5)	0.0633 (13)
H16A	0.0479	0.8806	0.1833	0.076*
H16B	0.0274	0.7306	0.2547	0.076*
C17	0.0610 (5)	0.8043 (5)	0.0731 (5)	0.0592 (13)
C18	−0.0058 (6)	0.6882 (6)	0.0703 (6)	0.0832 (18)
H18	−0.0419	0.6139	0.1421	0.100*
C19	−0.0198 (8)	0.6808 (7)	−0.0396 (7)	0.101 (2)
H19	−0.0622	0.6012	−0.0401	0.122*
C20	0.0281 (7)	0.7894 (7)	−0.1457 (7)	0.0879 (19)
H20	0.0160	0.7843	−0.2190	0.105*
C21	0.0934 (6)	0.9049 (7)	−0.1453 (6)	0.0787 (16)
H21	0.1278	0.9789	−0.2179	0.094*
C22	0.1090 (5)	0.9126 (5)	−0.0362 (5)	0.0638 (13)
H22	0.1527	0.9926	−0.0368	0.077*
C23	0.3265 (5)	0.9644 (4)	0.1802 (4)	0.0468 (11)
C24	0.2789 (5)	1.0641 (5)	0.1725 (5)	0.0617 (13)
H24	0.1857	1.0457	0.1974	0.074*
C25	0.3678 (6)	1.1891 (5)	0.1285 (5)	0.0628 (13)
H25	0.3328	1.2534	0.1246	0.075*
C26	0.5059 (6)	1.2221 (4)	0.0904 (4)	0.0553 (12)
C27	0.5511 (5)	1.1243 (5)	0.0954 (4)	0.0559 (12)
H27	0.6436	1.1439	0.0684	0.067*
C28	0.4643 (5)	0.9979 (4)	0.1390 (4)	0.0482 (11)
H28	0.4991	0.9345	0.1407	0.058*
C29	0.6054 (7)	1.3593 (5)	0.0429 (5)	0.0810 (17)
H29A	0.5769	1.4115	−0.0389	0.122*
H29B	0.7033	1.3578	0.0426	0.122*
H29C	0.5993	1.3956	0.0948	0.122*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br	0.0785 (4)	0.0635 (3)	0.0559 (3)	0.0306 (3)	0.0025 (3)	−0.0267 (3)
S	0.0587 (8)	0.0391 (6)	0.0652 (8)	0.0018 (5)	0.0160 (6)	−0.0211 (6)
O1	0.051 (2)	0.061 (2)	0.107 (3)	−0.0095 (16)	0.013 (2)	−0.051 (2)
O2	0.095 (3)	0.0491 (19)	0.071 (2)	0.0154 (19)	0.031 (2)	−0.0047 (18)
N1	0.053 (2)	0.041 (2)	0.052 (2)	0.0117 (17)	0.0025 (18)	−0.0218 (17)
N2	0.047 (2)	0.053 (2)	0.070 (3)	0.0193 (19)	−0.0052 (19)	−0.033 (2)
C1	0.056 (3)	0.033 (2)	0.047 (3)	0.012 (2)	0.001 (2)	−0.020 (2)
C2	0.057 (3)	0.032 (2)	0.044 (2)	0.013 (2)	0.000 (2)	−0.0170 (19)
C3	0.053 (3)	0.032 (2)	0.045 (3)	0.008 (2)	0.000 (2)	−0.0148 (19)
C4	0.058 (3)	0.038 (2)	0.059 (3)	0.013 (2)	−0.009 (2)	−0.020 (2)
C5	0.063 (3)	0.050 (3)	0.069 (4)	0.016 (3)	−0.015 (3)	−0.019 (3)
C6	0.095 (4)	0.063 (3)	0.050 (3)	0.027 (3)	−0.017 (3)	−0.022 (3)
C7	0.085 (4)	0.048 (3)	0.054 (3)	0.019 (3)	0.003 (3)	−0.017 (2)
C8	0.060 (3)	0.031 (2)	0.046 (3)	0.008 (2)	−0.003 (2)	−0.0152 (19)
C9	0.052 (3)	0.042 (2)	0.048 (3)	0.003 (2)	0.011 (2)	−0.020 (2)
C10	0.067 (3)	0.080 (4)	0.080 (4)	0.027 (3)	−0.014 (3)	−0.055 (3)
C11	0.103 (5)	0.089 (4)	0.082 (4)	0.057 (4)	−0.013 (4)	−0.046 (4)
C12	0.120 (5)	0.052 (3)	0.063 (4)	0.017 (3)	0.013 (4)	−0.030 (3)
C13	0.099 (5)	0.073 (4)	0.082 (4)	0.011 (4)	−0.006 (4)	−0.054 (3)
C14	0.080 (4)	0.069 (3)	0.066 (3)	0.023 (3)	−0.013 (3)	−0.036 (3)
C15	0.058 (3)	0.051 (3)	0.058 (3)	0.018 (2)	−0.010 (2)	−0.030 (2)
C16	0.046 (3)	0.069 (3)	0.075 (4)	0.016 (2)	−0.001 (3)	−0.034 (3)
C17	0.044 (3)	0.065 (3)	0.074 (4)	0.020 (2)	−0.011 (3)	−0.036 (3)
C18	0.078 (4)	0.078 (4)	0.089 (4)	0.017 (3)	−0.028 (3)	−0.046 (3)
C19	0.104 (5)	0.083 (5)	0.132 (6)	0.036 (4)	−0.053 (5)	−0.071 (5)
C20	0.084 (5)	0.114 (6)	0.096 (5)	0.049 (4)	−0.030 (4)	−0.067 (5)
C21	0.064 (4)	0.101 (5)	0.074 (4)	0.036 (3)	−0.012 (3)	−0.037 (4)
C22	0.052 (3)	0.068 (3)	0.079 (4)	0.024 (3)	−0.014 (3)	−0.039 (3)
C23	0.050 (3)	0.051 (3)	0.047 (3)	0.022 (2)	−0.012 (2)	−0.028 (2)
C24	0.054 (3)	0.060 (3)	0.083 (4)	0.023 (3)	0.009 (3)	−0.035 (3)
C25	0.076 (4)	0.060 (3)	0.067 (3)	0.030 (3)	0.005 (3)	−0.032 (3)
C26	0.070 (3)	0.052 (3)	0.042 (3)	0.023 (2)	−0.005 (2)	−0.017 (2)
C27	0.048 (3)	0.059 (3)	0.055 (3)	0.024 (2)	−0.002 (2)	−0.017 (2)
C28	0.057 (3)	0.049 (3)	0.045 (2)	0.027 (2)	−0.004 (2)	−0.021 (2)
C29	0.095 (4)	0.053 (3)	0.086 (4)	0.014 (3)	0.005 (3)	−0.027 (3)

Geometric parameters (Å, º)

Br—C2	1.873 (4)	C13—H13	0.9300
S—O1	1.416 (4)	C14—H14	0.9300
S—O2	1.421 (4)	C15—H15A	0.9700
S—N1	1.677 (4)	C15—H15B	0.9700
S—C9	1.747 (4)	C16—C17	1.501 (7)
N1—C8	1.410 (6)	C16—H16A	0.9700
N1—C1	1.419 (5)	C16—H16B	0.9700
N2—C23	1.419 (5)	C17—C22	1.379 (7)
N2—C16	1.469 (6)	C17—C18	1.374 (7)
N2—C15	1.466 (5)	C18—C19	1.395 (9)
C1—C2	1.352 (6)	C18—H18	0.9300
C1—C15	1.493 (6)	C19—C20	1.357 (9)
C2—C3	1.421 (6)	C19—H19	0.9300
C3—C4	1.396 (6)	C20—C21	1.351 (8)
C3—C8	1.394 (6)	C20—H20	0.9300
C4—C5	1.362 (7)	C21—C22	1.387 (8)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.374 (8)	C22—H22	0.9300
C5—H5	0.9300	C23—C28	1.378 (6)
C6—C7	1.384 (8)	C23—C24	1.393 (6)
C6—H6	0.9300	C24—C25	1.373 (7)
C7—C8	1.397 (7)	C24—H24	0.9300
C7—H7	0.9300	C25—C26	1.367 (7)
C9—C10	1.361 (7)	C25—H25	0.9300
C9—C14	1.379 (7)	C26—C27	1.372 (6)
C10—C11	1.379 (7)	C26—C29	1.514 (7)
C10—H10	0.9300	C27—C28	1.379 (6)
C11—C12	1.359 (8)	C27—H27	0.9300
C11—H11	0.9300	C28—H28	0.9300
C12—C13	1.346 (8)	C29—H29A	0.9600
C12—H12	0.9300	C29—H29B	0.9600
C13—C14	1.382 (7)	C29—H29C	0.9600
O1—S—O2	120.5 (2)	N2—C15—C1	115.8 (4)
O1—S—N1	107.4 (2)	N2—C15—H15A	108.3
O2—S—N1	105.3 (2)	C1—C15—H15A	108.3
O1—S—C9	109.0 (2)	N2—C15—H15B	108.3
O2—S—C9	107.4 (2)	C1—C15—H15B	108.3
N1—S—C9	106.30 (19)	H15A—C15—H15B	107.4
C8—N1—C1	108.1 (4)	N2—C16—C17	114.8 (4)
C8—N1—S	124.7 (3)	N2—C16—H16A	108.6
C1—N1—S	126.9 (3)	C17—C16—H16A	108.6
C23—N2—C16	117.7 (4)	N2—C16—H16B	108.6
C23—N2—C15	118.2 (4)	C17—C16—H16B	108.6
C16—N2—C15	112.1 (4)	H16A—C16—H16B	107.6
C2—C1—N1	106.6 (4)	C22—C17—C18	117.7 (5)
C2—C1—C15	127.7 (4)	C22—C17—C16	121.5 (5)
N1—C1—C15	125.5 (4)	C18—C17—C16	120.8 (5)
C1—C2—C3	111.2 (4)	C17—C18—C19	120.5 (6)
C1—C2—Br	126.4 (3)	C17—C18—H18	119.7
C3—C2—Br	122.4 (3)	C19—C18—H18	119.7
C4—C3—C8	121.1 (4)	C20—C19—C18	120.3 (6)
C4—C3—C2	133.0 (4)	C20—C19—H19	119.8
C8—C3—C2	105.8 (4)	C18—C19—H19	119.8
C5—C4—C3	118.0 (5)	C21—C20—C19	120.2 (6)
C5—C4—H4	121.0	C21—C20—H20	119.9
C3—C4—H4	121.0	C19—C20—H20	119.9
C4—C5—C6	121.1 (5)	C20—C21—C22	119.7 (6)
C4—C5—H5	119.4	C20—C21—H21	120.1
C6—C5—H5	119.4	C22—C21—H21	120.1
C5—C6—C7	122.6 (5)	C17—C22—C21	121.5 (5)
C5—C6—H6	118.7	C17—C22—H22	119.2
C7—C6—H6	118.7	C21—C22—H22	119.2
C8—C7—C6	116.8 (5)	C28—C23—C24	117.0 (4)
C8—C7—H7	121.6	C28—C23—N2	123.4 (4)
C6—C7—H7	121.6	C24—C23—N2	119.5 (4)
C7—C8—C3	120.4 (5)	C25—C24—C23	120.9 (5)
C7—C8—N1	131.3 (5)	C25—C24—H24	119.5
C3—C8—N1	108.2 (4)	C23—C24—H24	119.5
C10—C9—C14	120.3 (5)	C26—C25—C24	122.3 (5)
C10—C9—S	119.3 (4)	C26—C25—H25	118.9
C14—C9—S	120.3 (4)	C24—C25—H25	118.9
C9—C10—C11	119.7 (5)	C25—C26—C27	116.6 (5)
C9—C10—H10	120.2	C25—C26—C29	122.8 (5)
C11—C10—H10	120.2	C27—C26—C29	120.6 (5)
C10—C11—C12	120.1 (6)	C26—C27—C28	122.4 (5)
C10—C11—H11	119.9	C26—C27—H27	118.8
C12—C11—H11	119.9	C28—C27—H27	118.8
C13—C12—C11	120.3 (5)	C23—C28—C27	120.7 (4)
C13—C12—H12	119.8	C23—C28—H28	119.6
C11—C12—H12	119.8	C27—C28—H28	119.6
C12—C13—C14	120.8 (5)	C26—C29—H29A	109.5
C12—C13—H13	119.6	C26—C29—H29B	109.5
C14—C13—H13	119.6	H29A—C29—H29B	109.5
C9—C14—C13	118.8 (5)	C26—C29—H29C	109.5
C9—C14—H14	120.6	H29A—C29—H29C	109.5
C13—C14—H14	120.6	H29B—C29—H29C	109.5
O1—S—N1—C8	−149.1 (3)	C14—C9—C10—C11	−0.2 (8)
O2—S—N1—C8	−19.5 (4)	S—C9—C10—C11	176.7 (4)
C9—S—N1—C8	94.2 (4)	C9—C10—C11—C12	−0.2 (9)
O1—S—N1—C1	23.8 (4)	C10—C11—C12—C13	0.5 (9)
O2—S—N1—C1	153.4 (3)	C11—C12—C13—C14	−0.3 (9)
C9—S—N1—C1	−92.8 (4)	C10—C9—C14—C13	0.3 (8)
C8—N1—C1—C2	1.2 (4)	S—C9—C14—C13	−176.6 (4)
S—N1—C1—C2	−172.6 (3)	C12—C13—C14—C9	0.0 (9)
C8—N1—C1—C15	176.6 (4)	C23—N2—C15—C1	68.1 (5)
S—N1—C1—C15	2.7 (6)	C16—N2—C15—C1	−149.9 (4)
N1—C1—C2—C3	−0.6 (5)	C2—C1—C15—N2	−127.4 (5)
C15—C1—C2—C3	−175.9 (4)	N1—C1—C15—N2	58.2 (6)
N1—C1—C2—Br	178.7 (3)	C23—N2—C16—C17	80.3 (5)
C15—C1—C2—Br	3.5 (6)	C15—N2—C16—C17	−62.0 (5)
C1—C2—C3—C4	−179.2 (4)	N2—C16—C17—C22	−69.1 (6)
Br—C2—C3—C4	1.4 (6)	N2—C16—C17—C18	109.2 (5)
C1—C2—C3—C8	−0.2 (5)	C22—C17—C18—C19	1.9 (8)
Br—C2—C3—C8	−179.6 (3)	C16—C17—C18—C19	−176.4 (5)
C8—C3—C4—C5	−1.8 (6)	C17—C18—C19—C20	−2.2 (10)
C2—C3—C4—C5	177.1 (4)	C18—C19—C20—C21	1.8 (10)
C3—C4—C5—C6	0.3 (7)	C19—C20—C21—C22	−1.2 (9)
C4—C5—C6—C7	1.1 (8)	C18—C17—C22—C21	−1.3 (8)
C5—C6—C7—C8	−1.1 (7)	C16—C17—C22—C21	177.0 (5)
C6—C7—C8—C3	−0.3 (6)	C20—C21—C22—C17	1.0 (8)
C6—C7—C8—N1	−178.3 (4)	C16—N2—C23—C28	−134.0 (4)
C4—C3—C8—C7	1.8 (6)	C15—N2—C23—C28	5.9 (6)
C2—C3—C8—C7	−177.4 (4)	C16—N2—C23—C24	48.8 (6)
C4—C3—C8—N1	−179.8 (4)	C15—N2—C23—C24	−171.3 (4)
C2—C3—C8—N1	1.0 (4)	C28—C23—C24—C25	−1.6 (7)
C1—N1—C8—C7	176.7 (4)	N2—C23—C24—C25	175.7 (4)
S—N1—C8—C7	−9.2 (6)	C23—C24—C25—C26	0.0 (8)
C1—N1—C8—C3	−1.4 (4)	C24—C25—C26—C27	1.5 (8)
S—N1—C8—C3	172.6 (3)	C24—C25—C26—C29	−179.4 (5)
O1—S—C9—C10	−0.8 (5)	C25—C26—C27—C28	−1.5 (7)
O2—S—C9—C10	−132.9 (4)	C29—C26—C27—C28	179.4 (4)
N1—S—C9—C10	114.7 (4)	C24—C23—C28—C27	1.7 (6)
O1—S—C9—C14	176.1 (4)	N2—C23—C28—C27	−175.6 (4)
O2—S—C9—C14	44.0 (5)	C26—C27—C28—C23	−0.1 (7)
N1—S—C9—C14	−68.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···N2	0.93	2.87	3.268 (7)	107
C14—H14···O2	0.93	2.81	3.025 (6)	95
C7—H7···O2	0.93	2.35	2.876 (7)	116