1-Ethyl-4'-(1H-indol-3-ylcarbon-yl)-1'-methyl-2,2''-dioxodi-spiro-[indoline-3,2'-pyrrolidine-3',3''-indoline]-4'-carbo-nitrile dimethyl sulfoxide monosolvate.

In the title compound, C31H25N5O3·C2H6OS, the three indole/indoline units are all essentially planar with maximum deviations of 0.0172 (3), 0.053 (2) and 0.07 (2) Å. The pyrrolidine ring adopts an envelope conformation with the C atoms bearing the 1-ethyl-2-oxo-indole substituent (in which the five-membered ring adopts a twisted conformation) as the flap. The dimethyl sulfoxide solvent mol-ecule is disordered over two positions, with an occupancy factor ratio of 0.871 (4):0.129 (4). The solvent components are linked to the heterocyclic mol-ecule via C-H⋯O and C-H⋯S hydrogen bonds. In the crystal, the solvent components are linked to the heterocyclic molecule via C-H⋯O and C-H⋯S inter-actions, forming R 2 (2)(10) ring motifs. The mol-ecules are further connected into a chain along the a-axis direction via N-H⋯O hydrogen bonds.

Related literature

For applications of indole derivatives, see: Barden (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C31H25N5O3·C2H6OS

M = 593.70

Orthorhombic,

a = 14.078 (5) Å

b = 20.416 (5) Å

c = 20.789 (5) Å

V = 5975 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.16 mm−1

T = 295 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.955, T max = 0.970

26724 measured reflections

5139 independent reflections

3447 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 1.03

5139 reflections

431 parameters

48 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813020485/rk2408sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020485/rk2408Isup2.hkl

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

C31H25N5O3·C2H6OS	F(000) = 2496
Mr = 593.70	Dx = 1.320 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5139 reflections
a = 14.078 (5) Å	θ = 2.2–25.0°
b = 20.416 (5) Å	µ = 0.16 mm−1
c = 20.789 (5) Å	T = 295 K
V = 5975 (3) Å3	Block, colourless
Z = 8	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	5139 independent reflections
Radiation source: fine-focus sealed tube	3447 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω and φ scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→15
Tmin = 0.955, Tmax = 0.970	k = −16→24
26724 measured reflections	l = −24→24

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0509P)2 + 2.1171P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
5139 reflections	Δρmax = 0.25 e Å−3
431 parameters	Δρmin = −0.27 e Å−3
48 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0015 (2)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.65192 (17)	0.06281 (11)	0.33748 (10)	0.0472 (6)
C2	0.5854 (2)	0.02329 (12)	0.36920 (13)	0.0661 (7)
H2	0.5206	0.0308	0.3648	0.079*
C3	0.6188 (3)	−0.02699 (14)	0.40713 (16)	0.0868 (10)
H3	0.5754	−0.0536	0.4285	0.104*
C4	0.7148 (3)	−0.03925 (14)	0.41453 (15)	0.0853 (10)
H4	0.7341	−0.0740	0.4403	0.102*
C5	0.7820 (2)	−0.00148 (13)	0.38480 (13)	0.0683 (8)
H5	0.8466	−0.0095	0.3898	0.082*
C6	0.74840 (18)	0.04948 (11)	0.34678 (10)	0.0501 (6)
C7	0.73904 (17)	0.13393 (11)	0.27982 (10)	0.0482 (6)
H7	0.7573	0.1679	0.2527	0.058*
C8	0.64624 (16)	0.11757 (10)	0.29381 (10)	0.0434 (5)
C9	0.55927 (17)	0.14783 (11)	0.27187 (10)	0.0470 (6)
C10	0.56313 (15)	0.20484 (10)	0.22079 (10)	0.0407 (5)
C11	0.62745 (17)	0.25514 (11)	0.24702 (11)	0.0468 (6)
C12	0.46423 (16)	0.23568 (11)	0.20902 (11)	0.0503 (6)
H12A	0.4175	0.2166	0.2378	0.060*
H12B	0.4663	0.2826	0.2163	0.060*
C13	0.52858 (15)	0.21989 (10)	0.10596 (10)	0.0399 (5)
C14	0.59516 (14)	0.18003 (9)	0.15212 (10)	0.0374 (5)
C15	0.36806 (17)	0.26636 (12)	0.11622 (13)	0.0619 (7)
H15A	0.3895	0.3107	0.1210	0.093*
H15B	0.3096	0.2606	0.1393	0.093*
H15C	0.3580	0.2571	0.0715	0.093*
C16	0.57207 (16)	0.10561 (10)	0.14492 (10)	0.0413 (5)
C17	0.69758 (15)	0.18221 (10)	0.13168 (9)	0.0382 (5)
C18	0.72407 (15)	0.12012 (11)	0.11078 (10)	0.0433 (5)
C19	0.81171 (18)	0.10731 (13)	0.08455 (12)	0.0598 (7)
H19	0.8281	0.0655	0.0707	0.072*
C20	0.87455 (19)	0.15900 (15)	0.07958 (13)	0.0695 (8)
H20	0.9344	0.1519	0.0619	0.083*
C21	0.85034 (17)	0.22058 (14)	0.10016 (13)	0.0617 (7)
H21	0.8940	0.2545	0.0964	0.074*
C22	0.76217 (16)	0.23289 (12)	0.12629 (10)	0.0482 (6)
H22	0.7463	0.2748	0.1401	0.058*
C23	0.57066 (16)	0.28945 (11)	0.09338 (11)	0.0461 (5)
C24	0.57243 (16)	0.23597 (11)	−0.00259 (11)	0.0480 (6)
C25	0.52630 (15)	0.19253 (11)	0.03842 (10)	0.0426 (5)
C26	0.49175 (17)	0.13434 (12)	0.01454 (12)	0.0536 (6)
H26	0.4580	0.1057	0.0408	0.064*
C27	0.5084 (2)	0.11921 (15)	−0.05004 (13)	0.0680 (8)
H27	0.4859	0.0801	−0.0671	0.082*
C28	0.5577 (2)	0.16173 (16)	−0.08827 (13)	0.0713 (8)
H28	0.5699	0.1502	−0.1308	0.086*
C29	0.58995 (18)	0.22098 (14)	−0.06587 (12)	0.0632 (7)
H29	0.6224	0.2499	−0.0926	0.076*
C30	0.6331 (2)	0.35405 (14)	0.00144 (14)	0.0722 (8)
H30A	0.6172	0.3909	0.0288	0.087*
H30B	0.6025	0.3609	−0.0398	0.087*
C31	0.7364 (2)	0.35289 (15)	−0.00822 (14)	0.0824 (9)
H31A	0.7673	0.3436	0.0319	0.124*
H31B	0.7571	0.3947	−0.0239	0.124*
H31C	0.7523	0.3196	−0.0390	0.124*
C32	0.8172 (3)	−0.05035 (18)	0.2089 (2)	0.0967 (14)	0.871 (4)
H32A	0.8741	−0.0559	0.1840	0.145*	0.871 (4)
H32B	0.8265	−0.0684	0.2511	0.145*	0.871 (4)
H32C	0.8028	−0.0045	0.2125	0.145*	0.871 (4)
C33	0.6338 (4)	−0.0748 (3)	0.2305 (3)	0.1150 (16)	0.871 (4)
H33A	0.6239	−0.0284	0.2338	0.173*	0.871 (4)
H33B	0.6547	−0.0916	0.2712	0.173*	0.871 (4)
H33C	0.5753	−0.0957	0.2185	0.173*	0.871 (4)
S1	0.72223 (14)	−0.09108 (5)	0.17075 (6)	0.0784 (5)	0.871 (4)
C32'	0.735 (3)	−0.0416 (12)	0.2131 (13)	0.098 (3)	0.129 (4)
H32D	0.7569	−0.0172	0.1765	0.147*	0.129 (4)
H32E	0.7884	−0.0607	0.2349	0.147*	0.129 (4)
H32F	0.7021	−0.0127	0.2420	0.147*	0.129 (4)
C33'	0.569 (3)	−0.0689 (17)	0.2306 (18)	0.109 (4)	0.129 (4)
H33D	0.5729	−0.0220	0.2331	0.164*	0.129 (4)
H33E	0.5681	−0.0870	0.2732	0.164*	0.129 (4)
H33F	0.5117	−0.0810	0.2084	0.164*	0.129 (4)
S1'	0.6645 (11)	−0.0983 (4)	0.1898 (6)	0.101 (2)	0.129 (4)
N1	0.79922 (17)	0.09409 (9)	0.31071 (10)	0.0512 (5)
N2	0.67536 (17)	0.29310 (10)	0.27061 (10)	0.0656 (6)
N3	0.43995 (12)	0.22165 (8)	0.14198 (9)	0.0441 (5)
N4	0.64895 (14)	0.07659 (10)	0.11969 (9)	0.0475 (5)
N5	0.59495 (13)	0.29407 (9)	0.03049 (9)	0.0506 (5)
O1	0.48161 (12)	0.13018 (9)	0.29122 (9)	0.0708 (5)
O2	0.49819 (11)	0.07829 (7)	0.15947 (8)	0.0540 (4)
O3	0.57737 (12)	0.33293 (7)	0.13313 (8)	0.0601 (5)
O4	0.69303 (17)	−0.05270 (9)	0.11415 (10)	0.0955 (7)
H1A	0.8589 (18)	0.0966 (11)	0.3091 (12)	0.054 (8)*
H4A	0.6529 (17)	0.0356 (13)	0.1161 (12)	0.062 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0615 (16)	0.0409 (12)	0.0393 (12)	−0.0039 (11)	0.0042 (11)	−0.0048 (10)
C2	0.077 (2)	0.0549 (15)	0.0662 (17)	−0.0057 (14)	0.0170 (14)	0.0055 (13)
C3	0.113 (3)	0.0589 (18)	0.088 (2)	−0.0037 (18)	0.029 (2)	0.0228 (16)
C4	0.122 (3)	0.0550 (17)	0.079 (2)	0.0146 (18)	0.009 (2)	0.0199 (15)
C5	0.085 (2)	0.0548 (16)	0.0655 (17)	0.0089 (15)	−0.0058 (15)	0.0032 (13)
C6	0.0648 (17)	0.0405 (13)	0.0448 (13)	−0.0022 (11)	−0.0040 (12)	−0.0036 (10)
C7	0.0530 (15)	0.0473 (13)	0.0444 (13)	−0.0065 (11)	−0.0049 (11)	0.0037 (10)
C8	0.0472 (15)	0.0441 (12)	0.0389 (12)	−0.0044 (11)	0.0013 (10)	−0.0014 (10)
C9	0.0485 (15)	0.0509 (13)	0.0418 (13)	−0.0049 (11)	0.0087 (11)	−0.0026 (10)
C10	0.0398 (13)	0.0415 (12)	0.0408 (12)	0.0001 (10)	0.0053 (9)	−0.0028 (9)
C11	0.0543 (16)	0.0471 (13)	0.0389 (12)	0.0006 (12)	0.0039 (11)	−0.0016 (10)
C12	0.0481 (15)	0.0512 (14)	0.0515 (14)	0.0070 (11)	0.0088 (11)	−0.0056 (11)
C13	0.0345 (12)	0.0399 (12)	0.0451 (12)	0.0002 (9)	0.0026 (9)	0.0006 (9)
C14	0.0343 (12)	0.0373 (11)	0.0405 (12)	−0.0001 (9)	0.0042 (9)	−0.0016 (9)
C15	0.0467 (16)	0.0659 (16)	0.0732 (18)	0.0148 (12)	−0.0017 (13)	0.0018 (13)
C16	0.0412 (14)	0.0379 (11)	0.0449 (13)	0.0015 (10)	0.0005 (10)	−0.0003 (10)
C17	0.0364 (13)	0.0438 (12)	0.0344 (11)	0.0027 (10)	−0.0006 (9)	0.0008 (9)
C18	0.0385 (14)	0.0508 (13)	0.0405 (12)	0.0051 (11)	−0.0012 (10)	−0.0010 (10)
C19	0.0507 (17)	0.0676 (17)	0.0611 (16)	0.0177 (13)	0.0089 (12)	−0.0044 (13)
C20	0.0408 (16)	0.095 (2)	0.0724 (18)	0.0072 (15)	0.0150 (13)	0.0071 (16)
C21	0.0399 (15)	0.0752 (18)	0.0701 (17)	−0.0080 (13)	0.0053 (13)	0.0116 (15)
C22	0.0421 (14)	0.0542 (14)	0.0483 (13)	−0.0060 (11)	−0.0020 (11)	0.0037 (11)
C23	0.0412 (14)	0.0433 (13)	0.0539 (14)	0.0019 (10)	−0.0023 (11)	0.0040 (11)
C24	0.0385 (14)	0.0616 (15)	0.0438 (13)	0.0058 (11)	−0.0035 (10)	0.0041 (11)
C25	0.0349 (13)	0.0492 (13)	0.0439 (12)	0.0052 (10)	−0.0032 (10)	−0.0029 (10)
C26	0.0485 (15)	0.0563 (15)	0.0562 (15)	0.0023 (11)	−0.0063 (11)	−0.0068 (12)
C27	0.0685 (19)	0.0746 (19)	0.0609 (18)	0.0085 (15)	−0.0121 (14)	−0.0219 (15)
C28	0.0685 (19)	0.100 (2)	0.0459 (15)	0.0131 (17)	−0.0011 (14)	−0.0111 (16)
C29	0.0514 (16)	0.090 (2)	0.0482 (15)	0.0054 (14)	0.0008 (12)	0.0055 (14)
C30	0.068 (2)	0.0710 (18)	0.0780 (19)	−0.0083 (14)	0.0082 (15)	0.0260 (15)
C31	0.075 (2)	0.090 (2)	0.082 (2)	−0.0139 (17)	0.0022 (16)	0.0151 (17)
C32	0.122 (4)	0.069 (2)	0.099 (3)	0.013 (2)	−0.021 (3)	−0.023 (2)
C33	0.141 (4)	0.100 (3)	0.104 (3)	−0.005 (3)	0.031 (4)	−0.025 (3)
S1	0.1168 (12)	0.0372 (5)	0.0811 (7)	0.0140 (6)	−0.0054 (7)	−0.0141 (4)
C32'	0.130 (6)	0.070 (5)	0.094 (5)	0.000 (5)	0.010 (5)	−0.030 (5)
C33'	0.131 (8)	0.086 (7)	0.111 (7)	0.001 (8)	0.019 (8)	−0.017 (7)
S1'	0.125 (5)	0.072 (4)	0.107 (5)	0.004 (4)	0.006 (5)	−0.020 (4)
N1	0.0474 (14)	0.0503 (12)	0.0558 (13)	−0.0038 (10)	−0.0075 (11)	0.0002 (9)
N2	0.0839 (17)	0.0565 (13)	0.0565 (13)	−0.0127 (12)	−0.0081 (11)	−0.0086 (11)
N3	0.0367 (11)	0.0452 (10)	0.0505 (11)	0.0051 (8)	0.0016 (8)	−0.0018 (8)
N4	0.0482 (13)	0.0377 (11)	0.0565 (12)	0.0047 (10)	0.0022 (9)	−0.0080 (9)
N5	0.0497 (12)	0.0499 (11)	0.0523 (12)	−0.0026 (9)	0.0026 (9)	0.0098 (9)
O1	0.0512 (11)	0.0866 (13)	0.0746 (12)	−0.0016 (9)	0.0207 (9)	0.0231 (10)
O2	0.0473 (10)	0.0415 (9)	0.0732 (11)	−0.0066 (7)	0.0078 (8)	0.0011 (8)
O3	0.0705 (12)	0.0417 (9)	0.0683 (11)	−0.0048 (8)	0.0002 (9)	−0.0053 (8)
O4	0.145 (2)	0.0573 (12)	0.0838 (15)	0.0281 (12)	−0.0163 (13)	−0.0165 (11)

C1—C6	1.399 (3)	C20—H20	0.9300
C1—C2	1.401 (3)	C21—C22	1.378 (3)
C1—C8	1.442 (3)	C21—H21	0.9300
C2—C3	1.377 (4)	C22—H22	0.9300
C2—H2	0.9300	C23—O3	1.216 (3)
C3—C4	1.383 (5)	C23—N5	1.355 (3)
C3—H3	0.9300	C24—C29	1.373 (3)
C4—C5	1.368 (4)	C24—C25	1.391 (3)
C4—H4	0.9300	C24—N5	1.407 (3)
C5—C6	1.389 (3)	C25—C26	1.376 (3)
C5—H5	0.9300	C26—C27	1.397 (3)
C6—N1	1.380 (3)	C26—H26	0.9300
C7—N1	1.339 (3)	C27—C28	1.366 (4)
C7—C8	1.379 (3)	C27—H27	0.9300
C7—H7	0.9300	C28—C29	1.373 (4)
C8—C9	1.445 (3)	C28—H28	0.9300
C9—O1	1.219 (3)	C29—H29	0.9300
C9—C10	1.577 (3)	C30—N5	1.467 (3)
C10—C11	1.474 (3)	C30—C31	1.468 (4)
C10—C12	1.547 (3)	C30—H30A	0.9700
C10—C14	1.580 (3)	C30—H30B	0.9700
C11—N2	1.138 (3)	C31—H31A	0.9600
C12—N3	1.463 (3)	C31—H31B	0.9600
C12—H12A	0.9700	C31—H31C	0.9600
C12—H12B	0.9700	C32—S1	1.764 (4)
C13—N3	1.456 (3)	C32—H32A	0.9600
C13—C25	1.512 (3)	C32—H32B	0.9600
C13—C23	1.561 (3)	C32—H32C	0.9600
C13—C14	1.569 (3)	C33—S1	1.790 (5)
C14—C17	1.504 (3)	C33—H33A	0.9600
C14—C16	1.561 (3)	C33—H33B	0.9600
C15—N3	1.464 (3)	C33—H33C	0.9600
C15—H15A	0.9600	S1—O4	1.472 (2)
C15—H15B	0.9600	C32'—S1'	1.60 (3)
C15—H15C	0.9600	C32'—H32D	0.9600
C16—O2	1.218 (2)	C32'—H32E	0.9600
C16—N4	1.341 (3)	C32'—H32F	0.9600
C17—C22	1.382 (3)	C33'—S1'	1.70 (3)
C17—C18	1.391 (3)	C33'—H33D	0.9600
C18—C19	1.374 (3)	C33'—H33E	0.9600
C18—N4	1.394 (3)	C33'—H33F	0.9600
C19—C20	1.381 (4)	S1'—O4	1.871 (14)
C19—H19	0.9300	N1—H1A	0.84 (2)
C20—C21	1.371 (4)	N4—H4A	0.84 (3)
C6—C1—C2	118.1 (2)	C21—C20—H20	119.4
C6—C1—C8	107.0 (2)	C19—C20—H20	119.4
C2—C1—C8	134.9 (2)	C20—C21—C22	120.9 (2)
C3—C2—C1	118.1 (3)	C20—C21—H21	119.5
C3—C2—H2	120.9	C22—C21—H21	119.5
C1—C2—H2	120.9	C21—C22—C17	119.2 (2)
C2—C3—C4	122.1 (3)	C21—C22—H22	120.4
C2—C3—H3	118.9	C17—C22—H22	120.4
C4—C3—H3	118.9	O3—C23—N5	125.8 (2)
C5—C4—C3	121.5 (3)	O3—C23—C13	125.4 (2)
C5—C4—H4	119.2	N5—C23—C13	108.72 (19)
C3—C4—H4	119.2	C29—C24—C25	121.9 (2)
C4—C5—C6	116.4 (3)	C29—C24—N5	128.0 (2)
C4—C5—H5	121.8	C25—C24—N5	110.06 (19)
C6—C5—H5	121.8	C26—C25—C24	119.6 (2)
N1—C6—C5	128.8 (3)	C26—C25—C13	131.4 (2)
N1—C6—C1	107.4 (2)	C24—C25—C13	108.89 (19)
C5—C6—C1	123.7 (2)	C25—C26—C27	118.5 (2)
N1—C7—C8	110.6 (2)	C25—C26—H26	120.7
N1—C7—H7	124.7	C27—C26—H26	120.7
C8—C7—H7	124.7	C28—C27—C26	120.3 (3)
C7—C8—C1	105.5 (2)	C28—C27—H27	119.9
C7—C8—C9	129.2 (2)	C26—C27—H27	119.9
C1—C8—C9	125.2 (2)	C27—C28—C29	122.0 (3)
O1—C9—C8	121.9 (2)	C27—C28—H28	119.0
O1—C9—C10	118.1 (2)	C29—C28—H28	119.0
C8—C9—C10	119.94 (19)	C24—C29—C28	117.5 (3)
C11—C10—C12	109.13 (18)	C24—C29—H29	121.2
C11—C10—C9	106.63 (17)	C28—C29—H29	121.2
C12—C10—C9	112.08 (17)	N5—C30—C31	113.9 (2)
C11—C10—C14	112.47 (17)	N5—C30—H30A	108.8
C12—C10—C14	104.15 (16)	C31—C30—H30A	108.8
C9—C10—C14	112.44 (16)	N5—C30—H30B	108.8
N2—C11—C10	176.2 (2)	C31—C30—H30B	108.8
N3—C12—C10	106.32 (17)	H30A—C30—H30B	107.7
N3—C12—H12A	110.5	C30—C31—H31A	109.5
C10—C12—H12A	110.5	C30—C31—H31B	109.5
N3—C12—H12B	110.5	H31A—C31—H31B	109.5
C10—C12—H12B	110.5	C30—C31—H31C	109.5
H12A—C12—H12B	108.7	H31A—C31—H31C	109.5
N3—C13—C25	117.96 (18)	H31B—C31—H31C	109.5
N3—C13—C23	112.90 (17)	O4—S1—C32	108.70 (19)
C25—C13—C23	100.88 (17)	O4—S1—C33	105.2 (2)
N3—C13—C14	102.13 (16)	C32—S1—C33	97.3 (2)
C25—C13—C14	112.90 (16)	S1'—C32'—H32D	109.5
C23—C13—C14	110.34 (17)	S1'—C32'—H32E	109.5
C17—C14—C16	101.62 (16)	H32D—C32'—H32E	109.5
C17—C14—C13	112.62 (17)	S1'—C32'—H32F	109.5
C16—C14—C13	108.76 (16)	H32D—C32'—H32F	109.5
C17—C14—C10	121.29 (17)	H32E—C32'—H32F	109.5
C16—C14—C10	109.83 (16)	S1'—C33'—H33D	109.5
C13—C14—C10	102.46 (15)	S1'—C33'—H33E	109.5
N3—C15—H15A	109.5	H33D—C33'—H33E	109.5
N3—C15—H15B	109.5	S1'—C33'—H33F	109.5
H15A—C15—H15B	109.5	H33D—C33'—H33F	109.5
N3—C15—H15C	109.5	H33E—C33'—H33F	109.5
H15A—C15—H15C	109.5	C32'—S1'—C33'	94.8 (17)
H15B—C15—H15C	109.5	C32'—S1'—O4	76.2 (12)
O2—C16—N4	125.7 (2)	C33'—S1'—O4	114.4 (14)
O2—C16—C14	126.84 (19)	C7—N1—C6	109.5 (2)
N4—C16—C14	107.43 (19)	C7—N1—H1A	125.1 (17)
C22—C17—C18	118.7 (2)	C6—N1—H1A	125.3 (17)
C22—C17—C14	132.5 (2)	C13—N3—C12	107.13 (17)
C18—C17—C14	108.56 (18)	C13—N3—C15	114.81 (18)
C19—C18—C17	122.6 (2)	C12—N3—C15	112.82 (18)
C19—C18—N4	127.8 (2)	C16—N4—C18	112.51 (19)
C17—C18—N4	109.64 (19)	C16—N4—H4A	121.9 (17)
C18—C19—C20	117.4 (2)	C18—N4—H4A	124.8 (17)
C18—C19—H19	121.3	C23—N5—C24	110.86 (19)
C20—C19—H19	121.3	C23—N5—C30	123.2 (2)
C21—C20—C19	121.2 (2)	C24—N5—C30	125.8 (2)
C6—C1—C2—C3	−0.8 (4)	C22—C17—C18—N4	−179.31 (19)
C8—C1—C2—C3	178.4 (3)	C14—C17—C18—N4	−3.7 (2)
C1—C2—C3—C4	0.0 (4)	C17—C18—C19—C20	0.2 (4)
C2—C3—C4—C5	0.6 (5)	N4—C18—C19—C20	178.8 (2)
C3—C4—C5—C6	−0.2 (4)	C18—C19—C20—C21	0.1 (4)
C4—C5—C6—N1	−178.7 (2)	C19—C20—C21—C22	−0.3 (4)
C4—C5—C6—C1	−0.7 (4)	C20—C21—C22—C17	0.0 (4)
C2—C1—C6—N1	179.6 (2)	C18—C17—C22—C21	0.4 (3)
C8—C1—C6—N1	0.2 (2)	C14—C17—C22—C21	−174.0 (2)
C2—C1—C6—C5	1.2 (3)	N3—C13—C23—O3	45.5 (3)
C8—C1—C6—C5	−178.2 (2)	C25—C13—C23—O3	172.3 (2)
N1—C7—C8—C1	0.2 (2)	C14—C13—C23—O3	−68.1 (3)
N1—C7—C8—C9	179.1 (2)	N3—C13—C23—N5	−132.22 (19)
C6—C1—C8—C7	−0.3 (2)	C25—C13—C23—N5	−5.4 (2)
C2—C1—C8—C7	−179.5 (3)	C14—C13—C23—N5	114.21 (19)
C6—C1—C8—C9	−179.2 (2)	C29—C24—C25—C26	−4.0 (3)
C2—C1—C8—C9	1.5 (4)	N5—C24—C25—C26	175.3 (2)
C7—C8—C9—O1	−175.8 (2)	C29—C24—C25—C13	173.3 (2)
C1—C8—C9—O1	2.8 (3)	N5—C24—C25—C13	−7.4 (2)
C7—C8—C9—C10	5.0 (3)	N3—C13—C25—C26	−52.2 (3)
C1—C8—C9—C10	−176.37 (19)	C23—C13—C25—C26	−175.6 (2)
O1—C9—C10—C11	126.3 (2)	C14—C13—C25—C26	66.7 (3)
C8—C9—C10—C11	−54.5 (2)	N3—C13—C25—C24	130.97 (19)
O1—C9—C10—C12	6.9 (3)	C23—C13—C25—C24	7.6 (2)
C8—C9—C10—C12	−173.86 (18)	C14—C13—C25—C24	−110.2 (2)
O1—C9—C10—C14	−110.0 (2)	C24—C25—C26—C27	3.1 (3)
C8—C9—C10—C14	69.2 (2)	C13—C25—C26—C27	−173.4 (2)
C11—C10—C12—N3	126.58 (19)	C25—C26—C27—C28	−0.2 (4)
C9—C10—C12—N3	−115.54 (19)	C26—C27—C28—C29	−2.0 (4)
C14—C10—C12—N3	6.3 (2)	C25—C24—C29—C28	1.8 (4)
N3—C13—C14—C17	−168.92 (16)	N5—C24—C29—C28	−177.4 (2)
C25—C13—C14—C17	63.4 (2)	C27—C28—C29—C24	1.2 (4)
C23—C13—C14—C17	−48.6 (2)	C8—C7—N1—C6	−0.1 (3)
N3—C13—C14—C16	79.25 (19)	C5—C6—N1—C7	178.3 (2)
C25—C13—C14—C16	−48.4 (2)	C1—C6—N1—C7	−0.1 (2)
C23—C13—C14—C16	−160.48 (17)	C25—C13—N3—C12	167.45 (18)
N3—C13—C14—C10	−36.98 (18)	C23—C13—N3—C12	−75.4 (2)
C25—C13—C14—C10	−164.67 (17)	C14—C13—N3—C12	43.1 (2)
C23—C13—C14—C10	83.29 (19)	C25—C13—N3—C15	−66.4 (2)
C11—C10—C14—C17	27.0 (3)	C23—C13—N3—C15	50.7 (2)
C12—C10—C14—C17	145.03 (19)	C14—C13—N3—C15	169.20 (17)
C9—C10—C14—C17	−93.4 (2)	C10—C12—N3—C13	−31.4 (2)
C11—C10—C14—C16	145.00 (18)	C10—C12—N3—C15	−158.72 (18)
C12—C10—C14—C16	−96.96 (19)	O2—C16—N4—C18	−177.3 (2)
C9—C10—C14—C16	24.6 (2)	C14—C16—N4—C18	2.5 (2)
C11—C10—C14—C13	−99.54 (19)	C19—C18—N4—C16	−178.1 (2)
C12—C10—C14—C13	18.50 (19)	C17—C18—N4—C16	0.7 (3)
C9—C10—C14—C13	140.06 (17)	O3—C23—N5—C24	−176.3 (2)
C17—C14—C16—O2	175.5 (2)	C13—C23—N5—C24	1.4 (2)
C13—C14—C16—O2	−65.6 (3)	O3—C23—N5—C30	−0.3 (4)
C10—C14—C16—O2	45.8 (3)	C13—C23—N5—C30	177.3 (2)
C17—C14—C16—N4	−4.4 (2)	C29—C24—N5—C23	−176.9 (2)
C13—C14—C16—N4	114.59 (19)	C25—C24—N5—C23	3.8 (3)
C10—C14—C16—N4	−134.02 (18)	C29—C24—N5—C30	7.2 (4)
C16—C14—C17—C22	179.6 (2)	C25—C24—N5—C30	−172.1 (2)
C13—C14—C17—C22	63.4 (3)	C31—C30—N5—C23	102.0 (3)
C10—C14—C17—C22	−58.4 (3)	C31—C30—N5—C24	−82.7 (3)
C16—C14—C17—C18	4.8 (2)	C32—S1—O4—S1'	−131.2 (7)
C13—C14—C17—C18	−111.40 (19)	C33—S1—O4—S1'	−27.8 (6)
C10—C14—C17—C18	126.82 (19)	C32'—S1'—O4—S1	59.2 (13)
C22—C17—C18—C19	−0.5 (3)	C33'—S1'—O4—S1	148.3 (16)
C14—C17—C18—C19	175.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O4	0.84 (3)	1.89 (3)	2.714 (3)	166 (2)
N1—H1A···O2i	0.84 (3)	2.10 (3)	2.887 (3)	155 (2)
C22—H22···S1ii	0.93	2.85	3.717 (3)	157
C32—H32A···O3iii	0.96	2.60	3.219 (4)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O4	0.84 (3)	1.89 (3)	2.714 (3)	166 (2)
N1—H1A⋯O2i	0.84 (3)	2.10 (3)	2.887 (3)	155 (2)
C22—H22⋯S1ii	0.93	2.85	3.717 (3)	157
C32—H32A⋯O3iii	0.96	2.60	3.219 (4)	123

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