Synthesis and crystal structures of some bis­(3-methyl-1H-indol-2-yl)(salic­yl)methanes

Four 2,2′-bis­indolyl­methanes (BIMs), a useful class of polyindolyl species joined to a central carbon, were synthesized using salicyl­aldehyde derivatives and simple acid catalysis; these are 2-[bis­(3-methyl-1H-indol-2-yl)meth­yl]-6-methyl­phenol, (IIa), 2-[bis­(3-methyl-1H-indol-2-yl)meth­yl]-4,6-di­chloro­phenol, (IIb), 2-[bis­(3-methyl-1H-indol-2-yl)meth­yl]-4-nitro­phenol, (IIc), and 2-[bis­(3-methyl-1H-indol-2-yl)meth­yl]-4,6-di-tert-butyl­phenol, (IId). BIMs (IIa) and (IIb) were characterized crystallographically as the dimethyl sulfoxide (DMSO) disolvates, i.e. C₂₆H₂₄N₂O·2C₂H₆OS and C₂₅H₂₀Cl₂N₂O·2C₂H₆OS, respectively. Both form strikingly similar one-dimensional hydrogen-bonding chain motifs with the DMSO solvent molecules. BIM (IIa) packs into double layers of chains whose orientations alternate every double layer, while (IIb) forms more simply packed chains along the a axis. BIM (IIa) has a remarkably long c axis.

Computing details

For both structures, data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL2014 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL2014 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008).

2-[Bis(3-methyl-1H-indol-2-yl)methyl]-6-methylphenol dimethyl sulfoxide disolvate (IIa)

Crystal data

C26H24N2O·2C2H6OS	Dx = 1.261 Mg m^−3
Mr = 536.73	Cu Kα radiation, λ = 1.54178 Å
Tetragonal, P43212	Cell parameters from 9904 reflections
a = 9.0917 (3) Å	θ = 2.6–71.7°
c = 68.392 (3) Å	µ = 1.97 mm^−1
V = 5653.2 (4) Å^3	T = 125 K
Z = 8	Block, colourless
F(000) = 2288	0.25 × 0.25 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer	5288 independent reflections
Radiation source: Cu IuS micro-focus source	5266 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	Rint = 0.045
φ and ω scans	θmax = 70.1°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −10→10
Tmin = 0.62, Tmax = 0.74	k = −10→10
78707 measured reflections	l = −81→82

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.025	w = 1/[σ^2(Fo^2) + (0.0328P)^2 + 1.6253P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.066	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.17 e Å^−3
5288 reflections	Δρmin = −0.27 e Å^−3
351 parameters	Absolute structure: Refined as an inversion twin
3 restraints	Absolute structure parameter: 0.036 (13)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.11157 (5)	0.42851 (5)	0.37892 (2)	0.01942 (11)
S2	0.75475 (5)	0.98248 (6)	0.45876 (2)	0.02676 (12)
O1	0.48565 (15)	0.74002 (15)	0.43926 (2)	0.0233 (3)
H3B	0.575 (2)	0.759 (3)	0.4396 (3)	0.028*
O2	−0.01047 (14)	0.49413 (15)	0.39090 (2)	0.0236 (3)
O3	0.75343 (15)	0.84075 (15)	0.44736 (2)	0.0266 (3)
N1	0.04375 (16)	0.73618 (17)	0.41700 (2)	0.0159 (3)
H1B	0.034 (2)	0.651 (2)	0.4120 (3)	0.019*
N2	−0.05442 (17)	0.61492 (19)	0.46000 (2)	0.0198 (3)
H2B	−0.094 (3)	0.688 (2)	0.4542 (3)	0.024*
C1	0.19775 (19)	0.66872 (19)	0.44636 (2)	0.0152 (3)
H1C	0.2626	0.7252	0.4555	0.018*
C2	0.12071 (19)	0.78012 (19)	0.43352 (2)	0.0154 (3)
C3	0.11159 (19)	0.9296 (2)	0.43552 (2)	0.0175 (4)
C4	0.1776 (2)	1.0242 (2)	0.45126 (3)	0.0243 (4)
H4A	0.2438	1.0966	0.4453	0.036*
H4B	0.233	0.9623	0.4604	0.036*
H4C	0.0989	1.0753	0.4583	0.036*
C5	0.02391 (19)	0.9826 (2)	0.41953 (2)	0.0169 (4)
C6	−0.0269 (2)	1.1213 (2)	0.41366 (3)	0.0217 (4)
H6A	−0.0013	1.2067	0.4209	0.026*
C7	−0.1147 (2)	1.1326 (2)	0.39720 (3)	0.0247 (4)
H7A	−0.1496	1.2264	0.3932	0.03*
C8	−0.1529 (2)	1.0078 (2)	0.38630 (3)	0.0243 (4)
H8A	−0.2134	1.0185	0.3751	0.029*
C9	−0.1042 (2)	0.8694 (2)	0.39159 (3)	0.0209 (4)
H9A	−0.1298	0.7849	0.3842	0.025*
C10	−0.0161 (2)	0.8579 (2)	0.40826 (2)	0.0170 (4)
C11	0.0926 (2)	0.5805 (2)	0.45893 (2)	0.0168 (3)
C12	0.1222 (2)	0.4616 (2)	0.47071 (2)	0.0201 (4)
C13	0.2679 (2)	0.3896 (2)	0.47407 (3)	0.0267 (4)
H13A	0.2703	0.3471	0.4872	0.04*
H13B	0.3464	0.463	0.4728	0.04*
H13C	0.2827	0.3117	0.4644	0.04*
C14	−0.0149 (2)	0.4184 (2)	0.47928 (2)	0.0220 (4)
C15	−0.0572 (3)	0.3065 (2)	0.49230 (3)	0.0282 (4)
H15A	0.0133	0.2387	0.4972	0.034*
C16	−0.2031 (3)	0.2968 (3)	0.49783 (3)	0.0347 (5)
H16A	−0.2327	0.2218	0.5067	0.042*
C17	−0.3083 (3)	0.3959 (3)	0.49061 (3)	0.0370 (5)
H17A	−0.4077	0.3865	0.4947	0.044*
C18	−0.2709 (2)	0.5066 (3)	0.47775 (3)	0.0316 (5)
H18A	−0.3427	0.5729	0.4728	0.038*
C19	−0.1235 (2)	0.5172 (2)	0.47228 (3)	0.0230 (4)
C20	0.29747 (19)	0.5679 (2)	0.43447 (2)	0.0152 (3)
C21	0.44449 (19)	0.6081 (2)	0.43159 (2)	0.0165 (4)
C22	0.5419 (2)	0.5154 (2)	0.42152 (2)	0.0194 (4)
C23	0.7013 (2)	0.5564 (3)	0.41918 (3)	0.0277 (4)
H23A	0.7085	0.657	0.4142	0.042*
H23B	0.7485	0.4885	0.41	0.042*
H23C	0.7507	0.5503	0.4319	0.042*
C24	0.4876 (2)	0.3832 (2)	0.41422 (2)	0.0216 (4)
H24A	0.5521	0.3195	0.4073	0.026*
C25	0.3423 (2)	0.3420 (2)	0.41675 (3)	0.0218 (4)
H25A	0.3076	0.2512	0.4116	0.026*
C26	0.2477 (2)	0.4351 (2)	0.42686 (2)	0.0185 (4)
H26A	0.1478	0.4076	0.4286	0.022*
C27	0.0487 (3)	0.4290 (3)	0.35415 (3)	0.0360 (5)
H27A	0.1302	0.4027	0.3454	0.054*
H27B	0.0125	0.5273	0.3508	0.054*
H27C	−0.031	0.3573	0.3527	0.054*
C28	0.2473 (2)	0.5694 (2)	0.37660 (3)	0.0270 (4)
H28A	0.3224	0.5384	0.3672	0.04*
H28B	0.2935	0.5869	0.3893	0.04*
H28C	0.2006	0.6602	0.372	0.04*
C29	0.6256 (4)	0.9572 (3)	0.47815 (4)	0.0525 (7)
H29A	0.6045	1.0522	0.4843	0.079*
H29B	0.667	0.8899	0.4879	0.079*
H29C	0.5344	0.9155	0.4729	0.079*
C30	0.6488 (3)	1.1100 (3)	0.44490 (4)	0.0533 (7)
H30A	0.6438	1.204	0.4519	0.08*
H30B	0.5491	1.0712	0.4431	0.08*
H30C	0.695	1.125	0.4321	0.08*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0211 (2)	0.0164 (2)	0.0207 (2)	−0.00015 (16)	0.00330 (17)	−0.00267 (16)
S2	0.0231 (2)	0.0254 (3)	0.0318 (2)	−0.00597 (19)	0.00193 (19)	−0.00126 (19)
O1	0.0154 (6)	0.0232 (7)	0.0313 (7)	−0.0050 (5)	0.0026 (5)	−0.0076 (5)
O2	0.0191 (6)	0.0264 (7)	0.0251 (6)	−0.0025 (6)	0.0045 (5)	−0.0088 (5)
O3	0.0176 (7)	0.0255 (7)	0.0366 (7)	−0.0016 (6)	0.0002 (6)	−0.0035 (6)
N1	0.0170 (7)	0.0138 (7)	0.0167 (7)	−0.0005 (6)	−0.0016 (6)	−0.0026 (6)
N2	0.0168 (8)	0.0236 (8)	0.0189 (7)	0.0005 (6)	0.0028 (6)	0.0028 (6)
C1	0.0137 (8)	0.0157 (9)	0.0160 (8)	−0.0022 (6)	0.0004 (7)	−0.0019 (7)
C2	0.0116 (8)	0.0204 (9)	0.0140 (7)	−0.0018 (6)	0.0012 (6)	−0.0015 (6)
C3	0.0159 (9)	0.0184 (9)	0.0183 (8)	−0.0042 (7)	0.0024 (7)	−0.0028 (7)
C4	0.0273 (10)	0.0200 (10)	0.0255 (9)	−0.0036 (8)	−0.0042 (8)	−0.0054 (7)
C5	0.0133 (8)	0.0171 (9)	0.0204 (8)	−0.0025 (7)	0.0034 (6)	−0.0007 (7)
C6	0.0185 (9)	0.0166 (9)	0.0300 (9)	−0.0030 (7)	0.0032 (7)	0.0004 (7)
C7	0.0190 (9)	0.0215 (10)	0.0337 (10)	0.0012 (7)	0.0031 (8)	0.0089 (8)
C8	0.0192 (9)	0.0306 (10)	0.0231 (9)	0.0009 (8)	−0.0008 (7)	0.0060 (8)
C9	0.0202 (9)	0.0228 (10)	0.0197 (8)	−0.0020 (7)	−0.0014 (7)	−0.0001 (7)
C10	0.0148 (8)	0.0186 (9)	0.0174 (8)	−0.0021 (7)	0.0038 (7)	−0.0002 (7)
C11	0.0174 (9)	0.0192 (9)	0.0138 (8)	−0.0018 (7)	−0.0004 (7)	−0.0026 (6)
C12	0.0238 (10)	0.0231 (10)	0.0133 (8)	−0.0010 (7)	−0.0014 (7)	−0.0013 (7)
C13	0.0295 (11)	0.0296 (11)	0.0211 (9)	0.0017 (9)	−0.0076 (8)	0.0040 (8)
C14	0.0293 (10)	0.0238 (10)	0.0129 (8)	−0.0058 (8)	0.0007 (7)	−0.0020 (7)
C15	0.0397 (12)	0.0278 (11)	0.0169 (8)	−0.0075 (9)	0.0015 (8)	0.0014 (8)
C16	0.0452 (14)	0.0388 (13)	0.0200 (9)	−0.0183 (10)	0.0069 (9)	0.0030 (8)
C17	0.0323 (12)	0.0489 (14)	0.0299 (10)	−0.0152 (11)	0.0124 (9)	−0.0009 (10)
C18	0.0246 (11)	0.0415 (13)	0.0287 (10)	−0.0047 (9)	0.0077 (8)	−0.0005 (9)
C19	0.0243 (10)	0.0272 (10)	0.0174 (8)	−0.0053 (8)	0.0039 (7)	−0.0005 (7)
C20	0.0156 (8)	0.0170 (9)	0.0130 (7)	0.0010 (7)	−0.0017 (6)	0.0020 (6)
C21	0.0167 (8)	0.0186 (9)	0.0143 (7)	−0.0008 (7)	−0.0017 (6)	0.0011 (7)
C22	0.0174 (9)	0.0261 (10)	0.0146 (8)	0.0017 (8)	−0.0003 (7)	0.0008 (7)
C23	0.0172 (10)	0.0381 (12)	0.0279 (10)	0.0014 (8)	0.0035 (8)	−0.0072 (8)
C24	0.0242 (10)	0.0243 (10)	0.0164 (8)	0.0065 (8)	0.0000 (7)	−0.0013 (7)
C25	0.0279 (10)	0.0185 (9)	0.0189 (8)	0.0005 (7)	−0.0028 (7)	−0.0020 (7)
C26	0.0184 (9)	0.0209 (9)	0.0160 (8)	−0.0020 (7)	−0.0011 (7)	0.0011 (7)
C27	0.0368 (12)	0.0470 (14)	0.0243 (10)	−0.0047 (10)	0.0004 (9)	−0.0102 (9)
C28	0.0228 (10)	0.0313 (11)	0.0268 (9)	−0.0073 (8)	0.0024 (8)	0.0041 (8)
C29	0.073 (2)	0.0495 (16)	0.0346 (12)	−0.0184 (14)	0.0218 (13)	−0.0052 (11)
C30	0.0603 (18)	0.0428 (15)	0.0568 (15)	0.0215 (13)	0.0169 (14)	0.0133 (13)

Geometric parameters (Å, º)

S1—O2	1.5025 (13)	C13—H13B	0.98
S1—C28	1.786 (2)	C13—H13C	0.98
S1—C27	1.788 (2)	C14—C15	1.406 (3)
S2—O3	1.5062 (14)	C14—C19	1.418 (3)
S2—C30	1.781 (3)	C15—C16	1.382 (3)
S2—C29	1.786 (3)	C15—H15A	0.95
O1—C21	1.361 (2)	C16—C17	1.403 (4)
O1—H3B	0.826 (19)	C16—H16A	0.95
N1—C10	1.370 (2)	C17—C18	1.379 (3)
N1—C2	1.388 (2)	C17—H17A	0.95
N1—H1B	0.852 (18)	C18—C19	1.396 (3)
N2—C19	1.374 (2)	C18—H18A	0.95
N2—C11	1.374 (2)	C20—C26	1.390 (3)
N2—H2B	0.852 (18)	C20—C21	1.400 (3)
C1—C2	1.512 (2)	C21—C22	1.404 (3)
C1—C11	1.515 (2)	C22—C24	1.392 (3)
C1—C20	1.524 (2)	C22—C23	1.505 (3)
C1—H1C	1.0	C23—H23A	0.98
C2—C3	1.368 (3)	C23—H23B	0.98
C3—C5	1.437 (2)	C23—H23C	0.98
C3—C4	1.503 (2)	C24—C25	1.384 (3)
C4—H4A	0.98	C24—H24A	0.95
C4—H4B	0.98	C25—C26	1.391 (3)
C4—H4C	0.98	C25—H25A	0.95
C5—C6	1.402 (3)	C26—H26A	0.95
C5—C10	1.418 (2)	C27—H27A	0.98
C6—C7	1.384 (3)	C27—H27B	0.98
C6—H6A	0.95	C27—H27C	0.98
C7—C8	1.402 (3)	C28—H28A	0.98
C7—H7A	0.95	C28—H28B	0.98
C8—C9	1.382 (3)	C28—H28C	0.98
C8—H8A	0.95	C29—H29A	0.98
C9—C10	1.397 (3)	C29—H29B	0.98
C9—H9A	0.95	C29—H29C	0.98
C11—C12	1.375 (3)	C30—H30A	0.98
C12—C14	1.432 (3)	C30—H30B	0.98
C12—C13	1.496 (3)	C30—H30C	0.98
C13—H13A	0.98
O2—S1—C28	105.91 (9)	C16—C15—C14	118.8 (2)
O2—S1—C27	106.22 (10)	C16—C15—H15A	120.6
C28—S1—C27	97.75 (11)	C14—C15—H15A	120.6
O3—S2—C30	106.08 (12)	C15—C16—C17	121.2 (2)
O3—S2—C29	105.60 (11)	C15—C16—H16A	119.4
C30—S2—C29	97.09 (15)	C17—C16—H16A	119.4
C21—O1—H3B	117.4 (17)	C18—C17—C16	121.7 (2)
C10—N1—C2	108.84 (15)	C18—C17—H17A	119.2
C10—N1—H1B	121.4 (15)	C16—C17—H17A	119.2
C2—N1—H1B	129.7 (15)	C17—C18—C19	117.3 (2)
C19—N2—C11	109.26 (16)	C17—C18—H18A	121.4
C19—N2—H2B	126.6 (16)	C19—C18—H18A	121.4
C11—N2—H2B	124.1 (16)	N2—C19—C18	130.3 (2)
C2—C1—C11	113.04 (15)	N2—C19—C14	107.33 (17)
C2—C1—C20	111.66 (13)	C18—C19—C14	122.32 (19)
C11—C1—C20	111.07 (14)	C26—C20—C21	119.01 (16)
C2—C1—H1C	106.9	C26—C20—C1	121.91 (16)
C11—C1—H1C	106.9	C21—C20—C1	119.06 (15)
C20—C1—H1C	106.9	O1—C21—C20	116.01 (15)
C3—C2—N1	109.66 (16)	O1—C21—C22	123.02 (16)
C3—C2—C1	129.45 (16)	C20—C21—C22	120.97 (17)
N1—C2—C1	120.88 (15)	C24—C22—C21	118.09 (17)
C2—C3—C5	106.92 (15)	C24—C22—C23	121.17 (17)
C2—C3—C4	128.01 (17)	C21—C22—C23	120.72 (18)
C5—C3—C4	125.07 (17)	C22—C23—H23A	109.5
C3—C4—H4A	109.5	C22—C23—H23B	109.5
C3—C4—H4B	109.5	H23A—C23—H23B	109.5
H4A—C4—H4B	109.5	C22—C23—H23C	109.5
C3—C4—H4C	109.5	H23A—C23—H23C	109.5
H4A—C4—H4C	109.5	H23B—C23—H23C	109.5
H4B—C4—H4C	109.5	C25—C24—C22	121.83 (17)
C6—C5—C10	118.64 (16)	C25—C24—H24A	119.1
C6—C5—C3	134.63 (17)	C22—C24—H24A	119.1
C10—C5—C3	106.72 (15)	C24—C25—C26	119.20 (18)
C7—C6—C5	119.32 (18)	C24—C25—H25A	120.4
C7—C6—H6A	120.3	C26—C25—H25A	120.4
C5—C6—H6A	120.3	C20—C26—C25	120.90 (17)
C6—C7—C8	121.04 (18)	C20—C26—H26A	119.6
C6—C7—H7A	119.5	C25—C26—H26A	119.6
C8—C7—H7A	119.5	S1—C27—H27A	109.5
C9—C8—C7	121.21 (17)	S1—C27—H27B	109.5
C9—C8—H8A	119.4	H27A—C27—H27B	109.5
C7—C8—H8A	119.4	S1—C27—H27C	109.5
C8—C9—C10	117.75 (18)	H27A—C27—H27C	109.5
C8—C9—H9A	121.1	H27B—C27—H27C	109.5
C10—C9—H9A	121.1	S1—C28—H28A	109.5
N1—C10—C9	130.08 (17)	S1—C28—H28B	109.5
N1—C10—C5	107.86 (15)	H28A—C28—H28B	109.5
C9—C10—C5	122.04 (17)	S1—C28—H28C	109.5
N2—C11—C12	109.74 (16)	H28A—C28—H28C	109.5
N2—C11—C1	121.58 (16)	H28B—C28—H28C	109.5
C12—C11—C1	128.68 (17)	S2—C29—H29A	109.5
C11—C12—C14	106.59 (17)	S2—C29—H29B	109.5
C11—C12—C13	127.42 (17)	H29A—C29—H29B	109.5
C14—C12—C13	125.99 (17)	S2—C29—H29C	109.5
C12—C13—H13A	109.5	H29A—C29—H29C	109.5
C12—C13—H13B	109.5	H29B—C29—H29C	109.5
H13A—C13—H13B	109.5	S2—C30—H30A	109.5
C12—C13—H13C	109.5	S2—C30—H30B	109.5
H13A—C13—H13C	109.5	H30A—C30—H30B	109.5
H13B—C13—H13C	109.5	S2—C30—H30C	109.5
C15—C14—C19	118.82 (19)	H30A—C30—H30C	109.5
C15—C14—C12	134.1 (2)	H30B—C30—H30C	109.5
C19—C14—C12	107.08 (16)
C10—N1—C2—C3	−0.2 (2)	C1—C11—C12—C13	0.2 (3)
C10—N1—C2—C1	179.37 (15)	C13—C12—C14—C15	−0.2 (3)
C11—C1—C2—C3	104.8 (2)	C11—C12—C14—C19	−0.8 (2)
C20—C1—C2—C3	−129.06 (19)	C13—C12—C14—C19	179.36 (17)
C11—C1—C2—N1	−74.6 (2)	C19—C14—C15—C16	−0.1 (3)
C20—C1—C2—N1	51.5 (2)	C12—C14—C15—C16	179.4 (2)
N1—C2—C3—C5	0.3 (2)	C14—C15—C16—C17	0.3 (3)
C1—C2—C3—C5	−179.21 (16)	C15—C16—C17—C18	0.0 (3)
N1—C2—C3—C4	179.79 (17)	C16—C17—C18—C19	−0.6 (3)
C1—C2—C3—C4	0.3 (3)	C11—N2—C19—C18	−179.2 (2)
C2—C3—C5—C6	178.6 (2)	C11—N2—C19—C14	0.5 (2)
C4—C3—C5—C6	−0.9 (3)	C17—C18—C19—N2	−179.6 (2)
C2—C3—C5—C10	−0.3 (2)	C17—C18—C19—C14	0.8 (3)
C4—C3—C5—C10	−179.81 (17)	C15—C14—C19—N2	179.82 (16)
C10—C5—C6—C7	0.3 (3)	C12—C14—C19—N2	0.2 (2)
C3—C5—C6—C7	−178.47 (19)	C15—C14—C19—C18	−0.5 (3)
C5—C6—C7—C8	−0.3 (3)	C12—C14—C19—C18	179.91 (18)
C6—C7—C8—C9	−0.1 (3)	C2—C1—C20—C26	−91.34 (19)
C7—C8—C9—C10	0.3 (3)	C11—C1—C20—C26	35.8 (2)
C2—N1—C10—C9	−178.73 (18)	C2—C1—C20—C21	90.43 (18)
C2—N1—C10—C5	0.00 (19)	C11—C1—C20—C21	−142.40 (16)
C8—C9—C10—N1	178.30 (18)	C26—C20—C21—O1	179.42 (15)
C8—C9—C10—C5	−0.3 (3)	C1—C20—C21—O1	−2.3 (2)
C6—C5—C10—N1	−178.89 (16)	C26—C20—C21—C22	−1.2 (2)
C3—C5—C10—N1	0.19 (19)	C1—C20—C21—C22	177.04 (15)
C6—C5—C10—C9	0.0 (3)	O1—C21—C22—C24	−179.75 (16)
C3—C5—C10—C9	179.04 (17)	C20—C21—C22—C24	1.0 (2)
C19—N2—C11—C12	−1.0 (2)	O1—C21—C22—C23	1.8 (3)
C19—N2—C11—C1	179.67 (16)	C20—C21—C22—C23	−177.47 (17)
C2—C1—C11—N2	−7.9 (2)	C21—C22—C24—C25	−0.3 (3)
C20—C1—C11—N2	−134.34 (16)	C23—C22—C24—C25	178.07 (17)
C2—C1—C11—C12	172.89 (17)	C22—C24—C25—C26	0.0 (3)
C20—C1—C11—C12	46.5 (2)	C21—C20—C26—C25	0.9 (2)
N2—C11—C12—C14	1.1 (2)	C1—C20—C26—C25	−177.33 (16)
C1—C11—C12—C14	−179.65 (16)	C24—C25—C26—C20	−0.3 (3)
N2—C11—C12—C13	−179.05 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H3B···S2	0.83 (2)	2.92 (2)	3.5529 (14)	135 (2)
O1—H3B···O3	0.83 (2)	1.87 (2)	2.6594 (19)	161 (2)
N1—H1B···O2	0.85 (2)	2.07 (2)	2.876 (2)	158 (2)
N2—H2B···S2^i	0.85 (2)	3.03 (2)	3.7663 (18)	147 (2)
N2—H2B···O3^i	0.85 (2)	2.02 (2)	2.831 (2)	159 (2)
C28—H28C···S1^ii	0.98	2.98	3.528 (2)	117

Symmetry codes: (i) x−1, y, z; (ii) −x+1/2, y+1/2, −z+3/4.

2-[Bis(3-methyl-1H-indol-2-yl)methyl]-4,6-dichlorophenol dimethyl sulfoxide disolvate (IIb)

Crystal data

C25H20Cl2N2O·2C2H6OS	Z = 2
Mr = 591.58	F(000) = 620
Triclinic, P1	Dx = 1.347 Mg m^−3
a = 8.9836 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9082 (11) Å	Cell parameters from 9925 reflections
c = 15.7820 (16) Å	θ = 2.3–30.1°
α = 72.406 (2)°	µ = 0.40 mm^−1
β = 83.232 (2)°	T = 125 K
γ = 83.086 (2)°	Needle, colourless
V = 1458.1 (3) Å^3	0.38 × 0.08 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer	8941 independent reflections
Radiation source: fine-focus sealed tube	5592 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 8.3333 pixels mm^-1	θmax = 30.6°, θmin = 2.0°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −15→15
Tmin = 0.88, Tmax = 0.99	l = −22→22
37620 measured reflections

Refinement

Refinement on F^2	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.0502P)^2 + 0.3396P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
8941 reflections	Δρmax = 0.44 e Å^−3
358 parameters	Δρmin = −0.56 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.95276 (5)	0.29177 (5)	0.17012 (4)	0.02720 (13)
Cl2	0.52146 (7)	−0.02334 (5)	0.19381 (4)	0.03354 (14)
O1	0.71320 (16)	0.41999 (14)	0.27576 (10)	0.0247 (3)
H1	0.8040 (18)	0.426 (2)	0.2713 (16)	0.03*
N1	0.28744 (19)	0.47505 (17)	0.19624 (11)	0.0204 (4)
H3	0.289 (2)	0.4058 (17)	0.1797 (14)	0.024*
N2	0.16606 (18)	0.28860 (16)	0.39389 (11)	0.0194 (4)
H2	0.119 (2)	0.3477 (18)	0.3540 (13)	0.023*
C1	0.6752 (2)	0.31782 (19)	0.25444 (13)	0.0185 (4)
C2	0.7712 (2)	0.24821 (19)	0.20551 (13)	0.0191 (4)
C3	0.7245 (2)	0.14478 (19)	0.18501 (13)	0.0212 (4)
H3B	0.7902	0.0985	0.1513	0.025*
C4	0.5803 (2)	0.11067 (19)	0.21476 (13)	0.0215 (4)
C5	0.4821 (2)	0.17820 (18)	0.26277 (13)	0.0184 (4)
H5A	0.3831	0.1532	0.2822	0.022*
C6	0.5287 (2)	0.28215 (19)	0.28224 (13)	0.0174 (4)
C7	0.4251 (2)	0.36153 (19)	0.33353 (13)	0.0177 (4)
H7A	0.4917	0.3936	0.3672	0.021*
C8	0.3493 (2)	0.48047 (19)	0.27113 (13)	0.0190 (4)
C9	0.3287 (2)	0.60401 (19)	0.27694 (14)	0.0204 (4)
C10	0.3744 (2)	0.6526 (2)	0.34847 (15)	0.0280 (5)
H10A	0.4421	0.7208	0.3217	0.042*
H10B	0.4263	0.5813	0.3921	0.042*
H10C	0.2847	0.6873	0.3783	0.042*
C11	0.2503 (2)	0.68005 (19)	0.20210 (14)	0.0226 (4)
C12	0.1960 (3)	0.8106 (2)	0.17240 (16)	0.0307 (5)
H12A	0.2114	0.8689	0.2041	0.037*
C13	0.1200 (3)	0.8528 (2)	0.09637 (16)	0.0375 (6)
H13A	0.084	0.9412	0.0753	0.045*
C14	0.0951 (3)	0.7675 (2)	0.04972 (16)	0.0382 (6)
H14A	0.0414	0.7993	−0.0021	0.046*
C15	0.1465 (3)	0.6381 (2)	0.07707 (14)	0.0305 (5)
H15A	0.1289	0.5805	0.0454	0.037*
C16	0.2253 (2)	0.5960 (2)	0.15320 (14)	0.0231 (4)
C17	0.3184 (2)	0.28031 (19)	0.40270 (13)	0.0171 (4)
C18	0.3523 (2)	0.19046 (19)	0.48134 (13)	0.0184 (4)
C19	0.5050 (2)	0.1550 (2)	0.51574 (14)	0.0259 (5)
H19A	0.4949	0.1044	0.5787	0.039*
H19B	0.5527	0.2337	0.5097	0.039*
H19C	0.5673	0.1036	0.4813	0.039*
C20	0.2131 (2)	0.14161 (18)	0.52471 (13)	0.0180 (4)
C21	0.1738 (2)	0.0502 (2)	0.60616 (14)	0.0228 (4)
H21A	0.2488	0.0041	0.6445	0.027*
C22	0.0238 (2)	0.0284 (2)	0.62954 (14)	0.0258 (5)
H22A	−0.004	−0.0328	0.6847	0.031*
C23	−0.0874 (2)	0.0947 (2)	0.57346 (14)	0.0252 (5)
H23A	−0.1895	0.0782	0.5915	0.03*
C24	−0.0524 (2)	0.1836 (2)	0.49259 (14)	0.0219 (4)
H24A	−0.1282	0.2277	0.4543	0.026*
C25	0.0985 (2)	0.20628 (18)	0.46908 (13)	0.0176 (4)
S1	0.40865 (7)	0.30804 (6)	0.02242 (4)	0.03426 (15)
O2	0.27909 (17)	0.30604 (15)	0.09106 (10)	0.0307 (4)
C26	0.3947 (6)	0.1809 (3)	−0.0229 (2)	0.0918 (15)
H26A	0.4711	0.1854	−0.0733	0.138*
H26B	0.2944	0.1887	−0.0436	0.138*
H26C	0.411	0.098	0.0229	0.138*
C27	0.3618 (3)	0.4344 (3)	−0.07351 (17)	0.0472 (7)
H27A	0.4357	0.4299	−0.1236	0.071*
H27B	0.3625	0.5177	−0.0619	0.071*
H27C	0.2614	0.4259	−0.0883	0.071*
S2	0.93875 (6)	0.59594 (5)	0.34200 (4)	0.02281 (12)
O3	0.96828 (15)	0.48795 (14)	0.29857 (9)	0.0225 (3)
C28	0.8072 (3)	0.5408 (2)	0.43589 (15)	0.0289 (5)
H28A	0.7754	0.6105	0.4631	0.043*
H28B	0.8546	0.4667	0.4797	0.043*
H28C	0.7193	0.5149	0.4165	0.043*
C29	0.8165 (3)	0.7148 (2)	0.27206 (16)	0.0330 (5)
H29A	0.781	0.7828	0.3003	0.049*
H29B	0.7302	0.6744	0.2632	0.049*
H29C	0.8712	0.7525	0.2142	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0175 (2)	0.0322 (3)	0.0304 (3)	−0.0030 (2)	0.0056 (2)	−0.0094 (2)
Cl2	0.0365 (3)	0.0279 (3)	0.0444 (3)	−0.0034 (2)	−0.0054 (3)	−0.0218 (3)
O1	0.0150 (7)	0.0272 (8)	0.0373 (9)	−0.0054 (6)	0.0021 (6)	−0.0179 (7)
N1	0.0212 (9)	0.0207 (9)	0.0199 (9)	0.0007 (7)	0.0002 (7)	−0.0088 (7)
N2	0.0154 (8)	0.0213 (9)	0.0188 (9)	0.0009 (7)	−0.0040 (7)	−0.0018 (7)
C1	0.0183 (9)	0.0181 (10)	0.0189 (10)	−0.0015 (7)	−0.0021 (8)	−0.0048 (8)
C2	0.0164 (9)	0.0216 (10)	0.0169 (9)	−0.0019 (8)	0.0008 (7)	−0.0027 (8)
C3	0.0237 (10)	0.0219 (11)	0.0169 (10)	0.0027 (8)	0.0001 (8)	−0.0066 (8)
C4	0.0272 (11)	0.0180 (10)	0.0208 (10)	0.0000 (8)	−0.0056 (8)	−0.0074 (8)
C5	0.0170 (9)	0.0191 (10)	0.0194 (10)	−0.0008 (7)	−0.0033 (8)	−0.0059 (8)
C6	0.0161 (9)	0.0193 (10)	0.0171 (10)	0.0005 (7)	−0.0028 (7)	−0.0059 (8)
C7	0.0158 (9)	0.0202 (10)	0.0193 (10)	−0.0028 (7)	0.0004 (7)	−0.0092 (8)
C8	0.0139 (9)	0.0213 (10)	0.0222 (10)	−0.0029 (7)	0.0025 (8)	−0.0079 (8)
C9	0.0155 (9)	0.0208 (10)	0.0249 (11)	−0.0038 (8)	0.0037 (8)	−0.0079 (8)
C10	0.0274 (11)	0.0252 (12)	0.0350 (13)	−0.0035 (9)	−0.0024 (10)	−0.0138 (10)
C11	0.0202 (10)	0.0208 (11)	0.0243 (11)	−0.0023 (8)	0.0048 (8)	−0.0051 (9)
C12	0.0297 (12)	0.0220 (11)	0.0375 (13)	−0.0020 (9)	0.0042 (10)	−0.0071 (10)
C13	0.0397 (14)	0.0246 (12)	0.0358 (14)	0.0072 (10)	0.0040 (11)	0.0030 (11)
C14	0.0420 (14)	0.0408 (15)	0.0223 (12)	0.0086 (11)	0.0003 (10)	−0.0009 (11)
C15	0.0342 (12)	0.0335 (13)	0.0207 (11)	0.0043 (10)	0.0001 (9)	−0.0071 (10)
C16	0.0223 (10)	0.0241 (11)	0.0192 (10)	0.0020 (8)	0.0044 (8)	−0.0046 (9)
C17	0.0135 (9)	0.0206 (10)	0.0198 (10)	−0.0012 (7)	−0.0012 (7)	−0.0100 (8)
C18	0.0159 (9)	0.0204 (10)	0.0215 (10)	0.0003 (7)	−0.0037 (8)	−0.0101 (8)
C19	0.0228 (11)	0.0286 (12)	0.0268 (11)	−0.0004 (9)	−0.0086 (9)	−0.0071 (9)
C20	0.0198 (9)	0.0180 (10)	0.0180 (9)	0.0006 (7)	−0.0015 (8)	−0.0089 (8)
C21	0.0249 (10)	0.0218 (11)	0.0208 (10)	0.0012 (8)	−0.0042 (8)	−0.0052 (8)
C22	0.0293 (11)	0.0234 (11)	0.0223 (11)	−0.0045 (9)	0.0039 (9)	−0.0049 (9)
C23	0.0198 (10)	0.0237 (11)	0.0308 (12)	−0.0042 (8)	0.0042 (9)	−0.0076 (9)
C24	0.0168 (9)	0.0228 (11)	0.0255 (11)	0.0014 (8)	−0.0031 (8)	−0.0069 (9)
C25	0.0171 (9)	0.0175 (10)	0.0183 (10)	0.0001 (7)	−0.0021 (7)	−0.0060 (8)
S1	0.0322 (3)	0.0445 (4)	0.0241 (3)	0.0083 (3)	−0.0031 (2)	−0.0112 (3)
O2	0.0337 (9)	0.0352 (9)	0.0244 (8)	−0.0039 (7)	0.0028 (7)	−0.0123 (7)
C26	0.188 (5)	0.0422 (19)	0.0413 (18)	0.023 (2)	0.001 (2)	−0.0234 (16)
C27	0.0441 (16)	0.0484 (17)	0.0351 (15)	0.0010 (13)	0.0051 (12)	0.0033 (12)
S2	0.0190 (2)	0.0255 (3)	0.0262 (3)	−0.0027 (2)	−0.0035 (2)	−0.0102 (2)
O3	0.0176 (7)	0.0257 (8)	0.0257 (8)	0.0016 (6)	−0.0029 (6)	−0.0108 (6)
C28	0.0323 (12)	0.0315 (13)	0.0264 (12)	−0.0040 (10)	0.0023 (9)	−0.0151 (10)
C29	0.0389 (13)	0.0239 (12)	0.0337 (13)	0.0038 (10)	−0.0080 (10)	−0.0054 (10)

Geometric parameters (Å, º)

Cl1—C2	1.735 (2)	C15—C16	1.394 (3)
Cl2—C4	1.745 (2)	C15—H15A	0.95
O1—C1	1.348 (2)	C17—C18	1.369 (3)
O1—H1	0.819 (16)	C18—C20	1.433 (3)
N1—C16	1.372 (3)	C18—C19	1.499 (3)
N1—C8	1.384 (3)	C19—H19A	0.98
N1—H3	0.868 (15)	C19—H19B	0.98
N2—C25	1.378 (3)	C19—H19C	0.98
N2—C17	1.382 (2)	C20—C21	1.405 (3)
N2—H2	0.860 (15)	C20—C25	1.412 (3)
C1—C2	1.399 (3)	C21—C22	1.384 (3)
C1—C6	1.400 (3)	C21—H21A	0.95
C2—C3	1.386 (3)	C22—C23	1.398 (3)
C3—C4	1.381 (3)	C22—H22A	0.95
C3—H3B	0.95	C23—C24	1.378 (3)
C4—C5	1.385 (3)	C23—H23A	0.95
C5—C6	1.382 (3)	C24—C25	1.394 (3)
C5—H5A	0.95	C24—H24A	0.95
C6—C7	1.524 (3)	S1—O2	1.4910 (16)
C7—C17	1.506 (3)	S1—C26	1.765 (3)
C7—C8	1.513 (3)	S1—C27	1.766 (3)
C7—H7A	1.0	C26—H26A	0.98
C8—C9	1.367 (3)	C26—H26B	0.98
C9—C11	1.429 (3)	C26—H26C	0.98
C9—C10	1.499 (3)	C27—H27A	0.98
C10—H10A	0.98	C27—H27B	0.98
C10—H10B	0.98	C27—H27C	0.98
C10—H10C	0.98	S2—O3	1.5159 (15)
C11—C12	1.403 (3)	S2—C28	1.781 (2)
C11—C16	1.416 (3)	S2—C29	1.784 (2)
C12—C13	1.379 (3)	C28—H28A	0.98
C12—H12A	0.95	C28—H28B	0.98
C13—C14	1.401 (4)	C28—H28C	0.98
C13—H13A	0.95	C29—H29A	0.98
C14—C15	1.383 (3)	C29—H29B	0.98
C14—H14A	0.95	C29—H29C	0.98
C1—O1—H1	114.1 (17)	C18—C17—N2	109.88 (17)
C16—N1—C8	108.85 (17)	C18—C17—C7	127.48 (17)
C16—N1—H3	126.5 (15)	N2—C17—C7	122.63 (17)
C8—N1—H3	124.7 (15)	C17—C18—C20	106.51 (16)
C25—N2—C17	108.83 (16)	C17—C18—C19	126.09 (18)
C25—N2—H2	125.3 (15)	C20—C18—C19	127.37 (18)
C17—N2—H2	124.5 (15)	C18—C19—H19A	109.5
O1—C1—C2	124.28 (18)	C18—C19—H19B	109.5
O1—C1—C6	116.89 (17)	H19A—C19—H19B	109.5
C2—C1—C6	118.82 (18)	C18—C19—H19C	109.5
C3—C2—C1	121.37 (18)	H19A—C19—H19C	109.5
C3—C2—Cl1	119.28 (15)	H19B—C19—H19C	109.5
C1—C2—Cl1	119.35 (15)	C21—C20—C25	118.78 (18)
C4—C3—C2	118.36 (18)	C21—C20—C18	133.83 (18)
C4—C3—H3B	120.8	C25—C20—C18	107.39 (17)
C2—C3—H3B	120.8	C22—C21—C20	118.79 (19)
C3—C4—C5	121.68 (19)	C22—C21—H21A	120.6
C3—C4—Cl2	119.23 (16)	C20—C21—H21A	120.6
C5—C4—Cl2	119.07 (16)	C21—C22—C23	121.15 (19)
C6—C5—C4	119.72 (18)	C21—C22—H22A	119.4
C6—C5—H5A	120.1	C23—C22—H22A	119.4
C4—C5—H5A	120.1	C24—C23—C22	121.52 (19)
C5—C6—C1	120.03 (18)	C24—C23—H23A	119.2
C5—C6—C7	122.17 (17)	C22—C23—H23A	119.2
C1—C6—C7	117.81 (17)	C23—C24—C25	117.45 (19)
C17—C7—C8	114.17 (15)	C23—C24—H24A	121.3
C17—C7—C6	112.15 (16)	C25—C24—H24A	121.3
C8—C7—C6	111.54 (16)	N2—C25—C24	130.35 (18)
C17—C7—H7A	106.1	N2—C25—C20	107.35 (16)
C8—C7—H7A	106.1	C24—C25—C20	122.30 (18)
C6—C7—H7A	106.1	O2—S1—C26	107.07 (16)
C9—C8—N1	109.68 (18)	O2—S1—C27	106.71 (11)
C9—C8—C7	128.71 (18)	C26—S1—C27	96.12 (15)
N1—C8—C7	121.60 (17)	S1—C26—H26A	109.5
C8—C9—C11	106.87 (18)	S1—C26—H26B	109.5
C8—C9—C10	127.59 (19)	H26A—C26—H26B	109.5
C11—C9—C10	125.52 (19)	S1—C26—H26C	109.5
C9—C10—H10A	109.5	H26A—C26—H26C	109.5
C9—C10—H10B	109.5	H26B—C26—H26C	109.5
H10A—C10—H10B	109.5	S1—C27—H27A	109.5
C9—C10—H10C	109.5	S1—C27—H27B	109.5
H10A—C10—H10C	109.5	H27A—C27—H27B	109.5
H10B—C10—H10C	109.5	S1—C27—H27C	109.5
C12—C11—C16	119.1 (2)	H27A—C27—H27C	109.5
C12—C11—C9	133.9 (2)	H27B—C27—H27C	109.5
C16—C11—C9	107.05 (18)	O3—S2—C28	105.76 (9)
C13—C12—C11	118.7 (2)	O3—S2—C29	104.70 (10)
C13—C12—H12A	120.6	C28—S2—C29	98.67 (11)
C11—C12—H12A	120.6	S2—C28—H28A	109.5
C12—C13—C14	121.1 (2)	S2—C28—H28B	109.5
C12—C13—H13A	119.4	H28A—C28—H28B	109.5
C14—C13—H13A	119.4	S2—C28—H28C	109.5
C15—C14—C13	121.8 (2)	H28A—C28—H28C	109.5
C15—C14—H14A	119.1	H28B—C28—H28C	109.5
C13—C14—H14A	119.1	S2—C29—H29A	109.5
C14—C15—C16	117.1 (2)	S2—C29—H29B	109.5
C14—C15—H15A	121.5	H29A—C29—H29B	109.5
C16—C15—H15A	121.5	S2—C29—H29C	109.5
N1—C16—C15	130.2 (2)	H29A—C29—H29C	109.5
N1—C16—C11	107.54 (18)	H29B—C29—H29C	109.5
C15—C16—C11	122.2 (2)
O1—C1—C2—C3	−179.29 (18)	C12—C13—C14—C15	−0.7 (4)
C6—C1—C2—C3	−0.6 (3)	C13—C14—C15—C16	−0.3 (3)
O1—C1—C2—Cl1	1.0 (3)	C8—N1—C16—C15	−177.7 (2)
C6—C1—C2—Cl1	179.67 (15)	C8—N1—C16—C11	0.6 (2)
C1—C2—C3—C4	−0.5 (3)	C14—C15—C16—N1	179.2 (2)
Cl1—C2—C3—C4	179.20 (15)	C14—C15—C16—C11	1.1 (3)
C2—C3—C4—C5	1.0 (3)	C12—C11—C16—N1	−179.42 (18)
C2—C3—C4—Cl2	−177.35 (15)	C9—C11—C16—N1	−0.6 (2)
C3—C4—C5—C6	−0.4 (3)	C12—C11—C16—C15	−1.0 (3)
Cl2—C4—C5—C6	178.02 (15)	C9—C11—C16—C15	177.81 (19)
C4—C5—C6—C1	−0.8 (3)	C25—N2—C17—C18	2.0 (2)
C4—C5—C6—C7	179.01 (17)	C25—N2—C17—C7	−177.75 (17)
O1—C1—C6—C5	−179.94 (17)	C8—C7—C17—C18	−160.40 (19)
C2—C1—C6—C5	1.3 (3)	C6—C7—C17—C18	71.5 (2)
O1—C1—C6—C7	0.2 (3)	C8—C7—C17—N2	19.3 (3)
C2—C1—C6—C7	−178.56 (17)	C6—C7—C17—N2	−108.8 (2)
C5—C6—C7—C17	34.0 (2)	N2—C17—C18—C20	−1.0 (2)
C1—C6—C7—C17	−146.14 (17)	C7—C17—C18—C20	178.72 (18)
C5—C6—C7—C8	−95.5 (2)	N2—C17—C18—C19	−179.02 (18)
C1—C6—C7—C8	84.4 (2)	C7—C17—C18—C19	0.7 (3)
C16—N1—C8—C9	−0.3 (2)	C17—C18—C20—C21	−179.3 (2)
C16—N1—C8—C7	179.29 (17)	C19—C18—C20—C21	−1.3 (4)
C17—C7—C8—C9	95.4 (2)	C17—C18—C20—C25	−0.3 (2)
C6—C7—C8—C9	−136.1 (2)	C19—C18—C20—C25	177.66 (19)
C17—C7—C8—N1	−84.1 (2)	C25—C20—C21—C22	−1.0 (3)
C6—C7—C8—N1	44.3 (2)	C18—C20—C21—C22	177.9 (2)
N1—C8—C9—C11	−0.1 (2)	C20—C21—C22—C23	0.5 (3)
C7—C8—C9—C11	−179.64 (18)	C21—C22—C23—C24	0.5 (3)
N1—C8—C9—C10	178.40 (19)	C22—C23—C24—C25	−0.8 (3)
C7—C8—C9—C10	−1.2 (3)	C17—N2—C25—C24	177.8 (2)
C8—C9—C11—C12	179.0 (2)	C17—N2—C25—C20	−2.1 (2)
C10—C9—C11—C12	0.5 (4)	C23—C24—C25—N2	−179.8 (2)
C8—C9—C11—C16	0.4 (2)	C23—C24—C25—C20	0.2 (3)
C10—C9—C11—C16	−178.10 (19)	C21—C20—C25—N2	−179.32 (17)
C16—C11—C12—C13	0.0 (3)	C18—C20—C25—N2	1.5 (2)
C9—C11—C12—C13	−178.4 (2)	C21—C20—C25—C24	0.7 (3)
C11—C12—C13—C14	0.8 (3)	C18—C20—C25—C24	−178.47 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl1	0.82 (2)	2.63 (2)	3.0343 (15)	112 (2)
O1—H1···S2	0.82 (2)	2.87 (2)	3.3957 (15)	124 (2)
O1—H1···O3	0.82 (2)	1.84 (2)	2.5875 (19)	151 (2)
N1—H3···S1	0.87 (2)	3.02 (2)	3.7242 (18)	139 (2)
N1—H3···O2	0.87 (2)	2.03 (2)	2.841 (2)	155 (2)
N2—H2···S2^i	0.86 (2)	2.95 (2)	3.6286 (18)	137 (2)
N2—H2···O3^i	0.86 (2)	1.98 (2)	2.805 (2)	161 (2)

Symmetry code: (i) x−1, y, z.