1'-Allyl-1-(3,4-di-methyl-benzo-yl)-2-(4-methyl-1,3-thia-zol-5-yl)-1,2,5,6,7,7a-hexa-hydro-spiro-[pyrrolizine-3,3'-indolin]-2'-one.

In the title compound, C30H31N3O2S, the fused pyrrolidine ring bearing three substituents adopts an envelope conformation with the C atom bearing the benzoyl group as the flap. The other fused pyrrolidine ring adopts a twisted conformation about one of its C-C bonds. The dihedral angle between the isatin ring system and the methyl-thia-zole ring is 25.95 (8)°. An intra-molecular C-H⋯O inter-action closes an S(8) ring. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, generating C(11) chains propagating in [001].

Related literature

For general background to spiro compounds and their biological activity, see: Pradhan et al. (2006 ▶); Saeedi et al. (2010 ▶); Dandia et al. (2011 ▶). For uses of oxindole derivatives, see: Rajeswaran et al. (1999 ▶) and of pyrrolidine derivatives, see: Suzuki et al. (1994 ▶). For the biological activity of pyrrolidine derivatives, see: Cuzzocrea et al. (2002 ▶); Obniska et al. (2002 ▶); Amal Raj et al. (2003 ▶).

Experimental

Crystal data

C30H31N3O2S

M = 497.64

Monoclinic,

a = 14.5718 (4) Å

b = 9.7218 (2) Å

c = 18.2609 (5) Å

β = 94.604 (1)°

V = 2578.57 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 298 K

0.35 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.947, T max = 0.984

14973 measured reflections

4494 independent reflections

3647 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.112

S = 1.06

4494 reflections

328 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL2013.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814006990/hb7204sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006990/hb7204Isup2.hkl

CCDC reference: 994375

Additional supporting information: crystallographic information; 3D view; checkCIF report

C30H31N3O2S	F(000) = 1056
Mr = 497.64	Dx = 1.282 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.5718 (4) Å	Cell parameters from 7315 reflections
b = 9.7218 (2) Å	θ = 2.5–28.3°
c = 18.2609 (5) Å	µ = 0.16 mm−1
β = 94.604 (1)°	T = 298 K
V = 2578.57 (11) Å3	Block, colourless
Z = 4	0.35 × 0.20 × 0.10 mm

Bruker APEXII CCD diffractometer	3647 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.017
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θmax = 25.0°, θmin = 1.4°
Tmin = 0.947, Tmax = 0.984	h = −17→17
14973 measured reflections	k = −11→10
4494 independent reflections	l = −17→21

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0482P)2 + 1.2211P], where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
4494 reflections	Δρmax = 0.48 e Å−3
328 parameters	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.65413 (13)	0.39883 (19)	0.85262 (10)	0.0383 (4)
C2	0.58768 (14)	0.4613 (2)	0.80571 (11)	0.0518 (5)
H2	0.5986	0.5458	0.7841	0.062*
C3	0.50416 (14)	0.3940 (3)	0.79186 (12)	0.0581 (6)
H3	0.4582	0.4339	0.7605	0.070*
C4	0.48832 (14)	0.2689 (2)	0.82378 (12)	0.0552 (6)
H4	0.4323	0.2246	0.8132	0.066*
C5	0.55540 (13)	0.2081 (2)	0.87182 (11)	0.0461 (5)
H5	0.5441	0.1241	0.8938	0.055*
C6	0.63861 (12)	0.27365 (18)	0.88649 (10)	0.0350 (4)
C7	0.72224 (11)	0.23936 (17)	0.93863 (9)	0.0318 (4)
C8	0.78884 (12)	0.35889 (17)	0.92293 (9)	0.0325 (4)
C9	0.63441 (14)	0.3191 (2)	1.04689 (11)	0.0466 (5)
H9A	0.5829	0.3301	1.0103	0.056*
H9B	0.6563	0.4093	1.0629	0.056*
C10	0.60697 (16)	0.2348 (2)	1.11132 (13)	0.0564 (6)
H10A	0.6448	0.2578	1.1558	0.068*
H10B	0.5428	0.2497	1.1196	0.068*
C11	0.62314 (16)	0.0887 (2)	1.08836 (12)	0.0547 (6)
H11A	0.5721	0.0547	1.0560	0.066*
H11B	0.6320	0.0285	1.1307	0.066*
C12	0.71102 (13)	0.09952 (18)	1.04812 (10)	0.0376 (4)
H12	0.7650	0.0896	1.0833	0.045*
C13	0.72035 (12)	0.00419 (18)	0.98251 (10)	0.0345 (4)
H13	0.6581	−0.0167	0.9612	0.041*
C14	0.76642 (12)	0.09562 (17)	0.92753 (9)	0.0315 (4)
H14	0.8324	0.1013	0.9427	0.038*
C15	0.75471 (12)	0.03912 (18)	0.84903 (10)	0.0351 (4)
C16	0.81039 (12)	0.09678 (18)	0.79174 (9)	0.0330 (4)
C17	0.78684 (13)	0.06349 (19)	0.71827 (10)	0.0393 (4)
H17	0.7378	0.0045	0.7060	0.047*
C18	0.83632 (14)	0.1180 (2)	0.66390 (10)	0.0435 (5)
H18	0.8206	0.0938	0.6152	0.052*
C19	0.90914 (13)	0.2083 (2)	0.68006 (10)	0.0407 (4)
C20	0.93371 (12)	0.24228 (19)	0.75315 (10)	0.0379 (4)
C21	0.88487 (12)	0.18377 (19)	0.80783 (10)	0.0362 (4)
H21	0.9027	0.2036	0.8567	0.043*
C22	0.76718 (13)	−0.12999 (18)	1.00085 (10)	0.0374 (4)
C23	0.72805 (15)	−0.25530 (19)	1.00826 (11)	0.0456 (5)
N3	0.78804 (15)	−0.36140 (18)	1.02743 (10)	0.0574 (5)
C25	0.87117 (18)	−0.3172 (2)	1.03383 (12)	0.0587 (6)
H25	0.9209	−0.3750	1.0460	0.070*
C26	0.78500 (16)	0.5701 (2)	0.84570 (11)	0.0510 (5)
H26A	0.8461	0.5823	0.8701	0.061*
H26B	0.7483	0.6495	0.8569	0.061*
C27	0.79208 (15)	0.5635 (2)	0.76434 (12)	0.0545 (6)
H27	0.8124	0.4820	0.7445	0.065*
C28	0.77137 (17)	0.6652 (3)	0.72003 (13)	0.0625 (6)
H28A	0.7508	0.7480	0.7384	0.075*
H28B	0.7771	0.6554	0.6699	0.075*
C29	0.62774 (17)	−0.2887 (3)	0.99541 (17)	0.0746 (8)
H29A	0.6055	−0.3229	1.0400	0.112*
H29B	0.6191	−0.3575	0.9578	0.112*
H29C	0.5943	−0.2072	0.9802	0.112*
C30	0.96004 (16)	0.2666 (3)	0.61853 (12)	0.0646 (7)
H30A	0.9340	0.2307	0.5725	0.097*
H30B	1.0238	0.2413	0.6255	0.097*
H30C	0.9547	0.3650	0.6183	0.097*
C31	1.00940 (15)	0.3431 (3)	0.77401 (13)	0.0595 (6)
H31A	1.0671	0.3062	0.7612	0.089*
H31B	1.0123	0.3596	0.8260	0.089*
H31C	0.9972	0.4281	0.7482	0.089*
N1	0.74354 (10)	0.44675 (15)	0.87448 (8)	0.0393 (4)
N2	0.70847 (10)	0.23905 (14)	1.01728 (8)	0.0353 (3)
O1	0.69856 (10)	−0.05143 (15)	0.83445 (8)	0.0535 (4)
O2	0.86754 (9)	0.37134 (13)	0.94943 (7)	0.0409 (3)
S1	0.88481 (4)	−0.14445 (6)	1.01858 (3)	0.05538 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0442 (10)	0.0379 (10)	0.0324 (10)	−0.0008 (8)	0.0013 (8)	0.0026 (8)
C2	0.0567 (12)	0.0521 (13)	0.0457 (12)	0.0046 (10)	−0.0018 (10)	0.0158 (10)
C3	0.0466 (12)	0.0744 (16)	0.0514 (13)	0.0104 (11)	−0.0084 (10)	0.0065 (12)
C4	0.0405 (11)	0.0676 (15)	0.0562 (14)	−0.0054 (10)	−0.0048 (10)	−0.0061 (11)
C5	0.0438 (10)	0.0441 (11)	0.0501 (12)	−0.0068 (9)	0.0017 (9)	−0.0002 (9)
C6	0.0379 (9)	0.0337 (10)	0.0331 (10)	−0.0010 (8)	0.0019 (7)	0.0000 (7)
C7	0.0374 (9)	0.0277 (9)	0.0303 (9)	−0.0041 (7)	0.0032 (7)	0.0019 (7)
C8	0.0420 (10)	0.0284 (9)	0.0274 (9)	−0.0042 (7)	0.0036 (7)	−0.0019 (7)
C9	0.0562 (12)	0.0392 (11)	0.0459 (12)	0.0077 (9)	0.0131 (9)	0.0006 (9)
C10	0.0591 (13)	0.0564 (14)	0.0562 (14)	0.0026 (11)	0.0204 (11)	0.0020 (11)
C11	0.0724 (14)	0.0442 (12)	0.0514 (13)	−0.0075 (10)	0.0296 (11)	0.0017 (10)
C12	0.0495 (10)	0.0308 (9)	0.0331 (10)	0.0022 (8)	0.0075 (8)	0.0047 (8)
C13	0.0407 (9)	0.0283 (9)	0.0351 (10)	−0.0003 (7)	0.0069 (8)	0.0041 (7)
C14	0.0358 (9)	0.0282 (9)	0.0308 (9)	−0.0012 (7)	0.0038 (7)	0.0027 (7)
C15	0.0398 (9)	0.0298 (9)	0.0353 (10)	−0.0014 (8)	0.0009 (8)	−0.0002 (7)
C16	0.0386 (9)	0.0292 (9)	0.0312 (9)	0.0035 (7)	0.0032 (7)	0.0004 (7)
C17	0.0459 (10)	0.0357 (10)	0.0354 (10)	−0.0010 (8)	−0.0018 (8)	−0.0015 (8)
C18	0.0546 (11)	0.0484 (12)	0.0272 (9)	0.0077 (9)	0.0013 (8)	−0.0001 (8)
C19	0.0411 (10)	0.0446 (11)	0.0372 (10)	0.0101 (9)	0.0077 (8)	0.0063 (8)
C20	0.0346 (9)	0.0397 (10)	0.0400 (11)	0.0038 (8)	0.0060 (8)	0.0023 (8)
C21	0.0393 (9)	0.0390 (10)	0.0301 (9)	0.0023 (8)	0.0023 (7)	−0.0031 (8)
C22	0.0483 (10)	0.0331 (10)	0.0321 (10)	0.0043 (8)	0.0103 (8)	0.0035 (7)
C23	0.0635 (13)	0.0310 (10)	0.0439 (11)	0.0046 (9)	0.0147 (10)	0.0032 (8)
N3	0.0843 (14)	0.0359 (10)	0.0530 (11)	0.0144 (9)	0.0116 (10)	0.0062 (8)
C25	0.0804 (17)	0.0487 (13)	0.0464 (13)	0.0279 (12)	0.0009 (12)	0.0014 (10)
C26	0.0656 (13)	0.0370 (11)	0.0497 (12)	−0.0152 (10)	0.0008 (10)	0.0130 (9)
C27	0.0633 (13)	0.0458 (13)	0.0562 (14)	−0.0030 (10)	0.0160 (11)	0.0126 (10)
C28	0.0760 (16)	0.0611 (15)	0.0510 (14)	−0.0116 (12)	0.0082 (12)	0.0139 (11)
C29	0.0684 (16)	0.0407 (13)	0.117 (2)	−0.0092 (11)	0.0203 (15)	0.0028 (14)
C30	0.0615 (14)	0.0898 (19)	0.0442 (13)	−0.0014 (13)	0.0154 (11)	0.0134 (12)
C31	0.0477 (12)	0.0712 (16)	0.0601 (14)	−0.0150 (11)	0.0069 (11)	0.0050 (12)
N1	0.0468 (9)	0.0334 (8)	0.0368 (9)	−0.0089 (7)	−0.0016 (7)	0.0093 (7)
N2	0.0459 (8)	0.0285 (8)	0.0323 (8)	0.0006 (6)	0.0078 (7)	0.0018 (6)
O1	0.0681 (9)	0.0484 (9)	0.0446 (8)	−0.0245 (7)	0.0081 (7)	−0.0083 (6)
O2	0.0408 (7)	0.0399 (7)	0.0413 (7)	−0.0082 (6)	−0.0012 (6)	−0.0010 (6)
S1	0.0504 (3)	0.0509 (3)	0.0646 (4)	0.0101 (2)	0.0029 (3)	0.0022 (3)

C1—C2	1.381 (3)	C15—C16	1.484 (2)
C1—C6	1.392 (3)	C16—C21	1.389 (2)
C1—N1	1.411 (2)	C16—C17	1.396 (2)
C2—C3	1.387 (3)	C17—C18	1.379 (3)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.376 (3)	C18—C19	1.390 (3)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.391 (3)	C19—C20	1.394 (3)
C4—H4	0.9300	C19—C30	1.506 (3)
C5—C6	1.377 (3)	C20—C21	1.393 (3)
C5—H5	0.9300	C20—C31	1.502 (3)
C6—C7	1.522 (2)	C21—H21	0.9300
C7—N2	1.466 (2)	C22—C23	1.357 (3)
C7—C8	1.555 (2)	C22—S1	1.7244 (19)
C7—C14	1.559 (2)	C23—N3	1.379 (3)
C8—O2	1.214 (2)	C23—C29	1.497 (3)
C8—N1	1.362 (2)	N3—C25	1.282 (3)
C9—N2	1.468 (2)	C25—S1	1.716 (2)
C9—C10	1.514 (3)	C25—H25	0.9300
C9—H9A	0.9700	C26—N1	1.459 (2)
C9—H9B	0.9700	C26—C27	1.499 (3)
C10—C11	1.506 (3)	C26—H26A	0.9700
C10—H10A	0.9700	C26—H26B	0.9700
C10—H10B	0.9700	C27—C28	1.298 (3)
C11—C12	1.530 (3)	C27—H27	0.9300
C11—H11A	0.9700	C28—H28A	0.9300
C11—H11B	0.9700	C28—H28B	0.9300
C12—N2	1.468 (2)	C29—H29A	0.9600
C12—C13	1.529 (3)	C29—H29B	0.9600
C12—H12	0.9800	C29—H29C	0.9600
C13—C22	1.498 (2)	C30—H30A	0.9600
C13—C14	1.535 (2)	C30—H30B	0.9600
C13—H13	0.9800	C30—H30C	0.9600
C14—C15	1.532 (2)	C31—H31A	0.9600
C14—H14	0.9800	C31—H31B	0.9600
C15—O1	1.217 (2)	C31—H31C	0.9600
C2—C1—C6	121.97 (18)	C21—C16—C17	118.18 (16)
C2—C1—N1	128.02 (18)	C21—C16—C15	122.89 (16)
C6—C1—N1	110.01 (15)	C17—C16—C15	118.93 (16)
C1—C2—C3	117.8 (2)	C18—C17—C16	120.03 (18)
C1—C2—H2	121.1	C18—C17—H17	120.0
C3—C2—H2	121.1	C16—C17—H17	120.0
C4—C3—C2	120.95 (19)	C17—C18—C19	121.61 (18)
C4—C3—H3	119.5	C17—C18—H18	119.2
C2—C3—H3	119.5	C19—C18—H18	119.2
C3—C4—C5	120.6 (2)	C18—C19—C20	119.08 (17)
C3—C4—H4	119.7	C18—C19—C30	119.51 (18)
C5—C4—H4	119.7	C20—C19—C30	121.41 (19)
C6—C5—C4	119.3 (2)	C21—C20—C19	118.87 (17)
C6—C5—H5	120.4	C21—C20—C31	119.46 (17)
C4—C5—H5	120.4	C19—C20—C31	121.65 (17)
C5—C6—C1	119.34 (17)	C16—C21—C20	122.17 (17)
C5—C6—C7	131.98 (17)	C16—C21—H21	118.9
C1—C6—C7	108.61 (15)	C20—C21—H21	118.9
N2—C7—C6	116.59 (14)	C23—C22—C13	128.09 (18)
N2—C7—C8	108.57 (13)	C23—C22—S1	109.12 (14)
C6—C7—C8	101.61 (13)	C13—C22—S1	122.77 (14)
N2—C7—C14	102.47 (13)	C22—C23—N3	115.7 (2)
C6—C7—C14	115.69 (14)	C22—C23—C29	126.31 (19)
C8—C7—C14	112.06 (14)	N3—C23—C29	117.93 (19)
O2—C8—N1	126.11 (16)	C25—N3—C23	110.32 (19)
O2—C8—C7	125.75 (15)	N3—C25—S1	115.74 (17)
N1—C8—C7	108.14 (14)	N3—C25—H25	122.1
N2—C9—C10	104.31 (16)	S1—C25—H25	122.1
N2—C9—H9A	110.9	N1—C26—C27	112.65 (17)
C10—C9—H9A	110.9	N1—C26—H26A	109.1
N2—C9—H9B	110.9	C27—C26—H26A	109.1
C10—C9—H9B	110.9	N1—C26—H26B	109.1
H9A—C9—H9B	108.9	C27—C26—H26B	109.1
C11—C10—C9	103.73 (17)	H26A—C26—H26B	107.8
C11—C10—H10A	111.0	C28—C27—C26	123.7 (2)
C9—C10—H10A	111.0	C28—C27—H27	118.2
C11—C10—H10B	111.0	C26—C27—H27	118.2
C9—C10—H10B	111.0	C27—C28—H28A	120.0
H10A—C10—H10B	109.0	C27—C28—H28B	120.0
C10—C11—C12	102.96 (16)	H28A—C28—H28B	120.0
C10—C11—H11A	111.2	C23—C29—H29A	109.5
C12—C11—H11A	111.2	C23—C29—H29B	109.5
C10—C11—H11B	111.2	H29A—C29—H29B	109.5
C12—C11—H11B	111.2	C23—C29—H29C	109.5
H11A—C11—H11B	109.1	H29A—C29—H29C	109.5
N2—C12—C13	105.10 (14)	H29B—C29—H29C	109.5
N2—C12—C11	104.56 (15)	C19—C30—H30A	109.5
C13—C12—C11	117.70 (16)	C19—C30—H30B	109.5
N2—C12—H12	109.7	H30A—C30—H30B	109.5
C13—C12—H12	109.7	C19—C30—H30C	109.5
C11—C12—H12	109.7	H30A—C30—H30C	109.5
C22—C13—C12	114.85 (15)	H30B—C30—H30C	109.5
C22—C13—C14	115.80 (14)	C20—C31—H31A	109.5
C12—C13—C14	103.44 (14)	C20—C31—H31B	109.5
C22—C13—H13	107.4	H31A—C31—H31B	109.5
C12—C13—H13	107.4	C20—C31—H31C	109.5
C14—C13—H13	107.4	H31A—C31—H31C	109.5
C15—C14—C13	112.50 (14)	H31B—C31—H31C	109.5
C15—C14—C7	115.27 (14)	C8—N1—C1	111.42 (14)
C13—C14—C7	103.13 (13)	C8—N1—C26	123.80 (16)
C15—C14—H14	108.6	C1—N1—C26	124.68 (15)
C13—C14—H14	108.6	C7—N2—C12	112.11 (13)
C7—C14—H14	108.6	C7—N2—C9	121.47 (15)
O1—C15—C16	120.99 (16)	C12—N2—C9	110.19 (14)
O1—C15—C14	119.13 (16)	C25—S1—C22	89.08 (11)
C16—C15—C14	119.87 (15)
C6—C1—C2—C3	−1.1 (3)	C15—C16—C17—C18	178.67 (16)
N1—C1—C2—C3	179.66 (19)	C16—C17—C18—C19	−1.1 (3)
C1—C2—C3—C4	−0.1 (3)	C17—C18—C19—C20	1.3 (3)
C2—C3—C4—C5	1.1 (4)	C17—C18—C19—C30	−179.07 (19)
C3—C4—C5—C6	−0.8 (3)	C18—C19—C20—C21	0.5 (3)
C4—C5—C6—C1	−0.4 (3)	C30—C19—C20—C21	−179.18 (18)
C4—C5—C6—C7	175.96 (19)	C18—C19—C20—C31	−177.71 (19)
C2—C1—C6—C5	1.4 (3)	C30—C19—C20—C31	2.6 (3)
N1—C1—C6—C5	−179.25 (17)	C17—C16—C21—C20	2.6 (3)
C2—C1—C6—C7	−175.73 (18)	C15—C16—C21—C20	−176.85 (16)
N1—C1—C6—C7	3.6 (2)	C19—C20—C21—C16	−2.5 (3)
C5—C6—C7—N2	−63.4 (3)	C31—C20—C21—C16	175.78 (18)
C1—C6—C7—N2	113.23 (17)	C12—C13—C22—C23	101.5 (2)
C5—C6—C7—C8	178.8 (2)	C14—C13—C22—C23	−137.95 (19)
C1—C6—C7—C8	−4.58 (18)	C12—C13—C22—S1	−76.69 (19)
C5—C6—C7—C14	57.1 (3)	C14—C13—C22—S1	43.9 (2)
C1—C6—C7—C14	−126.20 (16)	C13—C22—C23—N3	−178.37 (17)
N2—C7—C8—O2	60.6 (2)	S1—C22—C23—N3	0.0 (2)
C6—C7—C8—O2	−175.91 (17)	C13—C22—C23—C29	3.7 (3)
C14—C7—C8—O2	−51.8 (2)	S1—C22—C23—C29	−178.0 (2)
N2—C7—C8—N1	−119.33 (15)	C22—C23—N3—C25	−0.5 (3)
C6—C7—C8—N1	4.11 (18)	C29—C23—N3—C25	177.7 (2)
C14—C7—C8—N1	128.21 (15)	C23—N3—C25—S1	0.8 (2)
N2—C9—C10—C11	−32.1 (2)	N1—C26—C27—C28	136.2 (2)
C9—C10—C11—C12	37.9 (2)	O2—C8—N1—C1	177.76 (17)
C10—C11—C12—N2	−29.4 (2)	C7—C8—N1—C1	−2.3 (2)
C10—C11—C12—C13	−145.56 (18)	O2—C8—N1—C26	1.3 (3)
N2—C12—C13—C22	152.65 (15)	C7—C8—N1—C26	−178.70 (17)
C11—C12—C13—C22	−91.5 (2)	C2—C1—N1—C8	178.46 (19)
N2—C12—C13—C14	25.51 (18)	C6—C1—N1—C8	−0.8 (2)
C11—C12—C13—C14	141.35 (17)	C2—C1—N1—C26	−5.1 (3)
C22—C13—C14—C15	72.1 (2)	C6—C1—N1—C26	175.59 (18)
C12—C13—C14—C15	−161.31 (14)	C27—C26—N1—C8	115.9 (2)
C22—C13—C14—C7	−163.02 (15)	C27—C26—N1—C1	−60.1 (3)
C12—C13—C14—C7	−36.48 (17)	C6—C7—N2—C12	108.89 (17)
N2—C7—C14—C15	156.57 (14)	C8—C7—N2—C12	−137.19 (15)
C6—C7—C14—C15	28.6 (2)	C14—C7—N2—C12	−18.49 (18)
C8—C7—C14—C15	−87.22 (17)	C6—C7—N2—C9	−24.4 (2)
N2—C7—C14—C13	33.57 (16)	C8—C7—N2—C9	89.54 (19)
C6—C7—C14—C13	−94.39 (17)	C14—C7—N2—C9	−151.77 (16)
C8—C7—C14—C13	149.78 (14)	C13—C12—N2—C7	−4.19 (19)
C13—C14—C15—O1	13.8 (2)	C11—C12—N2—C7	−128.77 (16)
C7—C14—C15—O1	−104.05 (19)	C13—C12—N2—C9	134.38 (16)
C13—C14—C15—C16	−167.26 (15)	C11—C12—N2—C9	9.8 (2)
C7—C14—C15—C16	74.9 (2)	C10—C9—N2—C7	147.77 (17)
O1—C15—C16—C21	−169.49 (18)	C10—C9—N2—C12	13.7 (2)
C14—C15—C16—C21	11.6 (3)	N3—C25—S1—C22	−0.64 (18)
O1—C15—C16—C17	11.0 (3)	C23—C22—S1—C25	0.32 (15)
C14—C15—C16—C17	−167.86 (15)	C13—C22—S1—C25	178.81 (16)
C21—C16—C17—C18	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O2	0.93	2.43	3.191 (2)	138
C30—H30A···O2i	0.96	2.57	3.533 (3)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O2	0.93	2.43	3.191 (2)	138
C30—H30A⋯O2i	0.96	2.57	3.533 (3)	178

Symmetry code: (i) .