2-{4-Methyl-N-[(2,3,4,9-tetra-hydro-1H-carbazol-3-yl)meth-yl]benzene-sulfon-amido}-ethyl 4-methyl-benzene-sulfonate.

In the title compound, C29H32N2O5S2, the indole ring system is nearly planar, with a maximum deviation of 0.013 (2) Å, and the cyclo-hexenone ring has an envelope conformation with the methine C atom as the flap. The two methyl-benzene rings are approximately perpendicular to each other, making a dihedral angle of 89.09 (8)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into a chain running along the a-axis direction, and weak C-H⋯O hydrogen bonds and C-H⋯π inter-actions are observed between the chains.

Related literature

For tetra­hydro­carbazole systems present in the framework of a number of indole-type alkaloids of biological inter­est, see: Saxton (1983 ▶). For related structures, see: Hökelek et al. (2009 ▶); Çaylak et al. (2007 ▶); Uludağ et al. (2009 ▶); Gündoğdu et al. (2011 ▶). For the use of tetra­hydro­carbazolone in the synthesis of central-nervous-system-active drugs, see: Romeo et al. (2006 ▶). For the syntheses of tetra­hydro­carbazolone-based anti­tumor-active compounds from tetra­hydro­carbazoles, see: Chen et al. (2009 ▶). For the syntheses of amino­tetra­hydro­carbazoles as central nervous system agents, see: Mooradian et al. (1977 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C29H32N2O5S2

M = 552.69

Monoclinic,

a = 10.5719 (5) Å

b = 10.8783 (6) Å

c = 23.8868 (11) Å

β = 93.507 (2)°

V = 2741.9 (2) Å3

Z = 4

Cu Kα radiation

μ = 2.11 mm−1

T = 150 K

0.21 × 0.16 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.701, T max = 0.761

168526 measured reflections

5101 independent reflections

4955 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.116

S = 1.05

5101 reflections

349 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813031097/xu5750sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031097/xu5750Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C29H32N2O5S2	F(000) = 1168
Mr = 552.69	Dx = 1.339 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 9835 reflections
a = 10.5719 (5) Å	θ = 3.7–69.1°
b = 10.8783 (6) Å	µ = 2.11 mm−1
c = 23.8868 (11) Å	T = 150 K
β = 93.507 (2)°	Block, pink
V = 2741.9 (2) Å3	0.21 × 0.16 × 0.13 mm
Z = 4

Bruker Kappa APEXII CCD area-detector diffractometer	5101 independent reflections
Radiation source: fine-focus sealed tube	4955 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 69.3°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.701, Tmax = 0.761	k = −12→9
168526 measured reflections	l = −28→28

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0702P)2 + 1.3803P] where P = (Fo2 + 2Fc2)/3
5101 reflections	(Δ/σ)max = 0.001
349 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

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. 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
S1	0.74839 (4)	0.45706 (4)	0.440644 (18)	0.03720 (14)
S2	0.91673 (4)	0.22863 (4)	0.250089 (17)	0.03013 (13)
O1	0.79745 (12)	0.41437 (12)	0.38233 (5)	0.0376 (3)
O2	0.79715 (13)	0.36599 (15)	0.47877 (6)	0.0483 (4)
O3	0.77959 (14)	0.58320 (14)	0.44931 (6)	0.0477 (3)
O4	0.85386 (12)	0.11380 (11)	0.23933 (6)	0.0414 (3)
O5	1.01947 (11)	0.23485 (13)	0.29196 (6)	0.0401 (3)
N1	0.81003 (12)	0.32611 (12)	0.26881 (6)	0.0279 (3)
N9	0.26066 (13)	0.12277 (12)	0.33533 (6)	0.0274 (3)
H9	0.183 (2)	0.1403 (18)	0.3313 (8)	0.029 (5)*
C1	0.33412 (15)	0.27199 (16)	0.26254 (7)	0.0323 (4)
H1A	0.2622	0.2488	0.2362	0.039*
H1B	0.3134	0.3508	0.2806	0.039*
C2	0.45468 (16)	0.28622 (18)	0.23078 (8)	0.0364 (4)
H2A	0.4602	0.2173	0.2040	0.044*
H2B	0.4497	0.3636	0.2090	0.044*
C3	0.57387 (15)	0.28803 (15)	0.26999 (7)	0.0309 (4)
H3	0.5629	0.3536	0.2986	0.037*
C4	0.59305 (14)	0.16623 (15)	0.30117 (7)	0.0289 (3)
H4A	0.6225	0.1027	0.2753	0.035*
H4B	0.6585	0.1761	0.3323	0.035*
C4A	0.47025 (14)	0.12658 (14)	0.32400 (6)	0.0256 (3)
C5	0.52340 (16)	−0.03680 (15)	0.40220 (7)	0.0297 (3)
H5	0.6127	−0.0374	0.3996	0.036*
C5A	0.44685 (15)	0.04014 (13)	0.36752 (6)	0.0252 (3)
C6	0.46753 (17)	−0.11183 (16)	0.44023 (7)	0.0358 (4)
H6	0.5192	−0.1639	0.4640	0.043*
C7	0.33587 (17)	−0.11239 (17)	0.44440 (8)	0.0365 (4)
H7	0.2996	−0.1660	0.4704	0.044*
C8	0.25776 (16)	−0.03621 (15)	0.41124 (7)	0.0314 (4)
H8	0.1686	−0.0359	0.4144	0.038*
C8A	0.31414 (15)	0.03974 (14)	0.37326 (6)	0.0258 (3)
C9A	0.35577 (14)	0.17487 (14)	0.30590 (7)	0.0268 (3)
C10	0.68646 (14)	0.32474 (15)	0.23591 (7)	0.0292 (3)
H10A	0.6918	0.2666	0.2043	0.035*
H10B	0.6703	0.4076	0.2199	0.035*
C11	0.85600 (16)	0.44698 (15)	0.28894 (7)	0.0308 (3)
H11A	0.8517	0.5055	0.2571	0.037*
H11B	0.9460	0.4394	0.3026	0.037*
C12	0.78106 (16)	0.49826 (16)	0.33539 (7)	0.0324 (4)
H12A	0.8126	0.5811	0.3463	0.039*
H12B	0.6903	0.5048	0.3229	0.039*
C13	0.58318 (17)	0.44288 (16)	0.43154 (7)	0.0321 (4)
C14	0.52784 (17)	0.32846 (16)	0.43769 (7)	0.0328 (4)
H14	0.5789	0.2582	0.4462	0.039*
C15	0.39759 (17)	0.31795 (16)	0.43132 (7)	0.0332 (4)
H15	0.3594	0.2399	0.4361	0.040*
C16	0.32127 (17)	0.41895 (16)	0.41813 (7)	0.0344 (4)
C17	0.37962 (19)	0.53315 (17)	0.41211 (8)	0.0411 (4)
H17	0.3288	0.6033	0.4032	0.049*
C18	0.50931 (19)	0.54588 (16)	0.41887 (8)	0.0393 (4)
H18	0.5477	0.6241	0.4149	0.047*
C19	0.17940 (19)	0.40483 (19)	0.41047 (9)	0.0445 (4)
H19A	0.1532	0.4090	0.3704	0.067*
H19B	0.1545	0.3252	0.4256	0.067*
H19C	0.1383	0.4711	0.4304	0.067*
C20	0.97518 (15)	0.27802 (14)	0.18609 (7)	0.0283 (3)
C21	1.05368 (15)	0.38076 (15)	0.18504 (7)	0.0305 (3)
H21	1.0743	0.4261	0.2183	0.037*
C22	1.10105 (16)	0.41571 (17)	0.13478 (8)	0.0346 (4)
H22	1.1539	0.4862	0.1338	0.041*
C23	1.07314 (16)	0.34982 (18)	0.08539 (7)	0.0363 (4)
C24	0.99322 (17)	0.24845 (17)	0.08763 (8)	0.0374 (4)
H24	0.9725	0.2028	0.0544	0.045*
C25	0.94355 (16)	0.21302 (16)	0.13735 (8)	0.0338 (4)
H25	0.8880	0.1445	0.1381	0.041*
C26	1.1295 (2)	0.3854 (2)	0.03154 (9)	0.0509 (5)
H26A	1.0676	0.3703	0.0000	0.076*
H26B	1.2058	0.3363	0.0267	0.076*
H26C	1.1518	0.4728	0.0327	0.076*

	U11	U22	U33	U12	U13	U23
S1	0.0384 (2)	0.0419 (3)	0.0316 (2)	−0.00848 (18)	0.00467 (17)	0.00134 (17)
S2	0.0248 (2)	0.0244 (2)	0.0415 (2)	0.00333 (14)	0.00396 (16)	0.00732 (15)
O1	0.0419 (7)	0.0361 (7)	0.0354 (6)	0.0008 (5)	0.0079 (5)	0.0068 (5)
O2	0.0413 (7)	0.0644 (9)	0.0388 (7)	−0.0054 (6)	−0.0007 (6)	0.0135 (6)
O3	0.0521 (8)	0.0474 (8)	0.0444 (7)	−0.0204 (7)	0.0113 (6)	−0.0087 (6)
O4	0.0390 (7)	0.0218 (6)	0.0642 (8)	0.0015 (5)	0.0102 (6)	0.0080 (5)
O5	0.0288 (6)	0.0466 (8)	0.0446 (7)	0.0086 (5)	0.0008 (5)	0.0120 (6)
N1	0.0234 (6)	0.0258 (7)	0.0348 (7)	0.0009 (5)	0.0039 (5)	0.0044 (5)
N9	0.0202 (6)	0.0273 (7)	0.0347 (7)	−0.0013 (5)	0.0028 (5)	0.0003 (5)
C1	0.0244 (8)	0.0316 (9)	0.0406 (9)	0.0017 (6)	0.0001 (7)	0.0076 (7)
C2	0.0299 (9)	0.0392 (10)	0.0399 (9)	0.0004 (7)	0.0012 (7)	0.0130 (7)
C3	0.0254 (8)	0.0277 (8)	0.0397 (9)	0.0013 (6)	0.0035 (6)	0.0087 (7)
C4	0.0231 (7)	0.0272 (8)	0.0367 (8)	0.0014 (6)	0.0032 (6)	0.0078 (6)
C4A	0.0251 (7)	0.0213 (7)	0.0305 (8)	−0.0009 (6)	0.0022 (6)	0.0014 (6)
C5	0.0291 (8)	0.0261 (8)	0.0342 (8)	0.0000 (6)	0.0032 (6)	0.0017 (6)
C5A	0.0263 (8)	0.0203 (7)	0.0292 (8)	−0.0031 (6)	0.0041 (6)	−0.0023 (6)
C6	0.0398 (9)	0.0306 (9)	0.0370 (9)	0.0007 (7)	0.0024 (7)	0.0077 (7)
C7	0.0417 (10)	0.0322 (9)	0.0365 (9)	−0.0075 (7)	0.0092 (7)	0.0056 (7)
C8	0.0294 (8)	0.0302 (8)	0.0351 (9)	−0.0067 (6)	0.0070 (7)	−0.0034 (6)
C8A	0.0266 (8)	0.0217 (7)	0.0294 (8)	−0.0024 (6)	0.0030 (6)	−0.0049 (6)
C9A	0.0237 (7)	0.0252 (8)	0.0317 (8)	−0.0020 (6)	0.0020 (6)	−0.0002 (6)
C10	0.0250 (8)	0.0292 (8)	0.0336 (8)	0.0012 (6)	0.0025 (6)	0.0076 (6)
C11	0.0299 (8)	0.0283 (8)	0.0347 (8)	−0.0031 (6)	0.0063 (6)	0.0035 (6)
C12	0.0338 (8)	0.0286 (8)	0.0350 (8)	−0.0012 (7)	0.0046 (7)	0.0037 (7)
C13	0.0396 (9)	0.0304 (8)	0.0267 (8)	−0.0045 (7)	0.0053 (7)	−0.0013 (6)
C14	0.0405 (9)	0.0257 (8)	0.0323 (8)	0.0002 (7)	0.0024 (7)	0.0004 (6)
C15	0.0422 (9)	0.0247 (8)	0.0325 (8)	−0.0039 (7)	0.0008 (7)	−0.0021 (6)
C16	0.0408 (9)	0.0308 (9)	0.0314 (8)	0.0003 (7)	0.0006 (7)	−0.0035 (7)
C17	0.0469 (11)	0.0262 (9)	0.0500 (11)	0.0044 (7)	0.0014 (8)	0.0023 (7)
C18	0.0503 (11)	0.0253 (9)	0.0428 (10)	−0.0047 (7)	0.0074 (8)	0.0013 (7)
C19	0.0429 (10)	0.0385 (10)	0.0513 (11)	0.0006 (8)	−0.0037 (8)	−0.0032 (8)
C20	0.0227 (7)	0.0241 (8)	0.0382 (9)	0.0043 (6)	0.0032 (6)	0.0000 (6)
C21	0.0270 (8)	0.0272 (8)	0.0375 (9)	−0.0006 (6)	0.0031 (6)	−0.0041 (6)
C22	0.0288 (8)	0.0327 (9)	0.0428 (9)	−0.0009 (7)	0.0070 (7)	0.0011 (7)
C23	0.0312 (8)	0.0413 (10)	0.0367 (9)	0.0114 (7)	0.0052 (7)	0.0007 (7)
C24	0.0337 (9)	0.0375 (9)	0.0404 (9)	0.0098 (7)	−0.0010 (7)	−0.0104 (8)
C25	0.0274 (8)	0.0263 (8)	0.0475 (10)	0.0029 (6)	0.0007 (7)	−0.0063 (7)
C26	0.0508 (12)	0.0624 (14)	0.0406 (10)	0.0102 (10)	0.0119 (9)	0.0045 (9)

S1—O1	1.5854 (13)	C9A—C1	1.487 (2)
S1—O2	1.4209 (15)	C9A—C4A	1.365 (2)
S1—O3	1.4234 (15)	C10—H10A	0.9900
S1—C13	1.7536 (18)	C10—H10B	0.9900
S2—O4	1.4308 (13)	C11—C12	1.509 (2)
S2—O5	1.4325 (13)	C11—H11A	0.9900
S2—N1	1.6305 (14)	C11—H11B	0.9900
S2—C20	1.7672 (17)	C12—H12A	0.9900
O1—C12	1.448 (2)	C12—H12B	0.9900
N1—C10	1.483 (2)	C13—C14	1.387 (2)
N1—C11	1.472 (2)	C13—C18	1.388 (3)
N9—C8A	1.376 (2)	C14—C15	1.381 (3)
N9—C9A	1.383 (2)	C14—H14	0.9500
N9—H9	0.84 (2)	C15—C16	1.388 (3)
C1—C2	1.530 (2)	C15—H15	0.9500
C1—H1A	0.9900	C16—C17	1.398 (3)
C1—H1B	0.9900	C16—C19	1.508 (3)
C2—C3	1.523 (2)	C17—C18	1.378 (3)
C2—H2A	0.9900	C17—H17	0.9500
C2—H2B	0.9900	C18—H18	0.9500
C3—C4	1.527 (2)	C19—H19A	0.9800
C3—C10	1.536 (2)	C19—H19B	0.9800
C3—H3	1.0000	C19—H19C	0.9800
C4—C4A	1.502 (2)	C20—C21	1.393 (2)
C4—H4A	0.9900	C20—C25	1.385 (2)
C4—H4B	0.9900	C21—C22	1.382 (2)
C5—C6	1.381 (2)	C21—H21	0.9500
C5—H5	0.9500	C22—C23	1.396 (3)
C5A—C4A	1.434 (2)	C22—H22	0.9500
C5A—C5	1.400 (2)	C23—C24	1.392 (3)
C6—C7	1.401 (3)	C23—C26	1.501 (3)
C6—H6	0.9500	C24—C25	1.382 (3)
C7—C8	1.384 (3)	C24—H24	0.9500
C7—H7	0.9500	C25—H25	0.9500
C8—H8	0.9500	C26—H26A	0.9800
C8A—C5A	1.418 (2)	C26—H26B	0.9800
C8A—C8	1.388 (2)	C26—H26C	0.9800
O1—S1—C13	104.01 (7)	N1—C10—C3	114.07 (13)
O2—S1—O1	103.50 (8)	N1—C10—H10A	108.7
O2—S1—O3	120.48 (9)	N1—C10—H10B	108.7
O2—S1—C13	109.74 (8)	C3—C10—H10A	108.7
O3—S1—O1	108.95 (8)	C3—C10—H10B	108.7
O3—S1—C13	108.84 (9)	H10A—C10—H10B	107.6
O4—S2—O5	119.39 (8)	N1—C11—C12	113.12 (13)
O4—S2—N1	107.19 (7)	N1—C11—H11A	109.0
O4—S2—C20	107.05 (8)	N1—C11—H11B	109.0
O5—S2—N1	106.59 (8)	C12—C11—H11A	109.0
O5—S2—C20	107.42 (8)	C12—C11—H11B	109.0
N1—S2—C20	108.90 (7)	H11A—C11—H11B	107.8
C12—O1—S1	117.76 (11)	O1—C12—C11	107.04 (14)
C10—N1—S2	116.74 (11)	O1—C12—H12A	110.3
C11—N1—S2	116.77 (10)	O1—C12—H12B	110.3
C11—N1—C10	116.39 (13)	C11—C12—H12A	110.3
C8A—N9—C9A	108.75 (13)	C11—C12—H12B	110.3
C8A—N9—H9	125.7 (13)	H12A—C12—H12B	108.6
C9A—N9—H9	125.5 (13)	C14—C13—S1	119.29 (14)
C2—C1—H1A	110.0	C14—C13—C18	120.80 (17)
C2—C1—H1B	110.0	C18—C13—S1	119.91 (14)
C9A—C1—C2	108.65 (13)	C13—C14—H14	120.4
C9A—C1—H1A	110.0	C15—C14—C13	119.13 (16)
C9A—C1—H1B	110.0	C15—C14—H14	120.4
H1B—C1—H1A	108.3	C14—C15—C16	121.43 (16)
C1—C2—H2A	109.1	C14—C15—H15	119.3
C1—C2—H2B	109.1	C16—C15—H15	119.3
C3—C2—C1	112.28 (14)	C15—C16—C17	118.20 (17)
C3—C2—H2A	109.1	C15—C16—C19	120.47 (16)
C3—C2—H2B	109.1	C17—C16—C19	121.33 (17)
H2A—C2—H2B	107.9	C16—C17—H17	119.4
C2—C3—C4	111.63 (14)	C18—C17—C16	121.29 (17)
C2—C3—C10	108.43 (14)	C18—C17—H17	119.4
C2—C3—H3	107.7	C13—C18—H18	120.4
C4—C3—C10	113.59 (13)	C17—C18—C13	119.14 (17)
C4—C3—H3	107.7	C17—C18—H18	120.4
C10—C3—H3	107.7	C16—C19—H19C	109.5
C3—C4—H4A	109.8	C16—C19—H19B	109.5
C3—C4—H4B	109.8	C16—C19—H19A	109.5
C4A—C4—C3	109.53 (13)	H19C—C19—H19B	109.5
C4A—C4—H4A	109.8	H19C—C19—H19A	109.5
C4A—C4—H4B	109.8	H19B—C19—H19A	109.5
H4A—C4—H4B	108.2	C21—C20—S2	119.98 (13)
C5A—C4A—C4	129.99 (14)	C25—C20—S2	119.51 (13)
C9A—C4A—C4	122.95 (14)	C25—C20—C21	120.51 (16)
C9A—C4A—C5A	107.03 (13)	C20—C21—H21	120.5
C5A—C5—H5	120.4	C22—C21—C20	118.96 (16)
C6—C5—C5A	119.20 (15)	C22—C21—H21	120.5
C6—C5—H5	120.4	C21—C22—C23	121.57 (17)
C5—C5A—C4A	134.57 (14)	C21—C22—H22	119.2
C5—C5A—C8A	118.71 (14)	C23—C22—H22	119.2
C8A—C5A—C4A	106.72 (13)	C22—C23—C26	121.15 (18)
C5—C6—C7	121.07 (16)	C24—C23—C22	118.13 (16)
C5—C6—H6	119.5	C24—C23—C26	120.71 (18)
C7—C6—H6	119.5	C23—C24—H24	119.4
C6—C7—H7	119.4	C25—C24—C23	121.14 (16)
C8—C7—C6	121.13 (15)	C25—C24—H24	119.4
C8—C7—H7	119.4	C20—C25—H25	120.2
C7—C8—C8A	117.73 (15)	C24—C25—C20	119.66 (16)
C7—C8—H8	121.1	C24—C25—H25	120.2
C8A—C8—H8	121.1	C23—C26—H26B	109.5
N9—C8A—C5A	107.66 (13)	C23—C26—H26C	109.5
N9—C8A—C8	130.19 (15)	C23—C26—H26A	109.5
C8—C8A—C5A	122.14 (15)	H26B—C26—H26A	109.5
N9—C9A—C1	124.01 (14)	H26B—C26—H26C	109.5
C4A—C9A—N9	109.84 (14)	H26C—C26—H26A	109.5
C4A—C9A—C1	126.12 (14)
O2—S1—O1—C12	−170.46 (12)	C5—C5A—C4A—C9A	−179.36 (17)
O3—S1—O1—C12	−41.11 (15)	C8A—C5A—C4A—C4	178.54 (16)
C13—S1—O1—C12	74.85 (13)	C8A—C5A—C4A—C9A	0.63 (17)
O1—S1—C13—C14	81.47 (14)	C4A—C5A—C5—C6	−179.06 (17)
O1—S1—C13—C18	−99.17 (15)	C8A—C5A—C5—C6	1.0 (2)
O2—S1—C13—C14	−28.72 (16)	C5—C6—C7—C8	−1.2 (3)
O2—S1—C13—C18	150.64 (15)	C6—C7—C8—C8A	0.7 (3)
O3—S1—C13—C14	−162.50 (13)	N9—C8A—C5A—C4A	−0.49 (16)
O3—S1—C13—C18	16.86 (17)	N9—C8A—C5A—C5	179.50 (14)
O4—S2—N1—C10	−43.26 (13)	C8—C8A—C5A—C4A	178.62 (14)
O4—S2—N1—C11	172.49 (12)	C8—C8A—C5A—C5	−1.4 (2)
O5—S2—N1—C10	−172.17 (11)	N9—C8A—C8—C7	179.43 (16)
O5—S2—N1—C11	43.58 (13)	C5A—C8A—C8—C7	0.5 (2)
C20—S2—N1—C10	72.23 (12)	N9—C9A—C1—C2	−167.88 (15)
C20—S2—N1—C11	−72.03 (13)	C4A—C9A—C1—C2	14.3 (2)
O4—S2—C20—C21	−172.61 (13)	N9—C9A—C4A—C4	−178.63 (14)
O4—S2—C20—C25	6.62 (15)	N9—C9A—C4A—C5A	−0.54 (18)
O5—S2—C20—C21	−43.26 (15)	C1—C9A—C4A—C4	−0.6 (3)
O5—S2—C20—C25	135.98 (13)	C1—C9A—C4A—C5A	177.54 (15)
N1—S2—C20—C21	71.81 (14)	N1—C11—C12—O1	62.68 (17)
N1—S2—C20—C25	−108.95 (13)	S1—C13—C14—C15	179.03 (13)
S1—O1—C12—C11	169.71 (11)	C18—C13—C14—C15	−0.3 (3)
S2—N1—C10—C3	116.55 (14)	S1—C13—C18—C17	−179.70 (14)
C11—N1—C10—C3	−99.06 (16)	C14—C13—C18—C17	−0.4 (3)
S2—N1—C11—C12	−144.48 (12)	C13—C14—C15—C16	1.0 (3)
C10—N1—C11—C12	71.14 (18)	C14—C15—C16—C17	−0.9 (3)
C9A—N9—C8A—C5A	0.17 (17)	C14—C15—C16—C19	179.01 (16)
C9A—N9—C8A—C8	−178.84 (16)	C15—C16—C17—C18	0.2 (3)
C8A—N9—C9A—C1	−177.89 (15)	C19—C16—C17—C18	−179.71 (18)
C8A—N9—C9A—C4A	0.24 (18)	C16—C17—C18—C13	0.4 (3)
C9A—C1—C2—C3	−44.4 (2)	S2—C20—C21—C22	178.25 (13)
C1—C2—C3—C4	63.82 (19)	C25—C20—C21—C22	−1.0 (2)
C1—C2—C3—C10	−170.31 (14)	S2—C20—C25—C24	−177.40 (13)
C2—C3—C4—C4A	−46.36 (19)	C21—C20—C25—C24	1.8 (2)
C10—C3—C4—C4A	−169.34 (14)	C20—C21—C22—C23	−0.7 (3)
C2—C3—C10—N1	−178.08 (14)	C21—C22—C23—C24	1.4 (3)
C4—C3—C10—N1	−53.4 (2)	C21—C22—C23—C26	−177.40 (17)
C3—C4—C4A—C5A	−161.21 (16)	C22—C23—C24—C25	−0.6 (3)
C3—C4—C4A—C9A	16.4 (2)	C26—C23—C24—C25	178.28 (17)
C5A—C5—C6—C7	0.3 (3)	C23—C24—C25—C20	−1.1 (3)
C5—C5A—C4A—C4	−1.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O5i	0.84 (2)	2.18 (2)	2.9561 (19)	154.1 (18)
C21—H21···O4ii	0.95	2.38	3.230 (2)	148
C8—H8···Cg5iii	0.95	2.81	3.5127 (18)	131
C10—H10B···Cg2iv	0.99	2.58	3.5538 (18)	168

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg5 are the centroids of the C4A/C5A/C8A/N9/C9A and C20–C25 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯O5i	0.84 (2)	2.18 (2)	2.9561 (19)	154.1 (18)
C21—H21⋯O4ii	0.95	2.38	3.230 (2)	148
C8—H8⋯Cg5iii	0.95	2.81	3.5127 (18)	131
C10—H10B⋯Cg2iv	0.99	2.58	3.5538 (18)	168

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .