1′-Methyl-3′,5′′-diphenyl-6′′,7′′,8′′,9′′,10′′,11′′-hexahydro-1H-indole-3-spiro-2′-pyrrolidine-4′-spiro-2′′-5′′H-cyclo­octeno[1,2-d]thia­zolo[3,2-a]pyrimidine-2,3′′(3H,2′′H)-dione

In the title compound, C₃₅H₃₄N₄O₂S, the five-membered pyrrolidine and thia­zole rings adopt envelope and twist conformations, respectively. The pyrimidine ring adopts a twist–boat conformation. The mol­ecular structure is stabilized by C—H...O and π–π intra­molecular inter­actions, and strong N—H...N inter­molecular hydrogen bonds stabilize the packing, in addition to van der Waals inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.053
• wR factor = 0.141
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.04 Ratio

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1'-Methyl-3',5''-diphenyl-5'',6'',7'',8'',9'',10'',11''1H-indole-3-spiro- 2'-pyrrolidine-4'-spiro-2''-cycloocteno[1,2-d]thiazolo[3,2-a]pyrimidine- 2,3''-dione

Crystal data

C35H34N4O2S	Z = 2
Mr = 574.72	F(000) = 608
Triclinic, P1	Dx = 1.283 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6368 (8) Å	Cell parameters from 6008 reflections
b = 12.1783 (9) Å	θ = 2.2–27.7°
c = 13.1467 (10) Å	µ = 0.15 mm^−1
α = 95.259 (1)°	T = 293 K
β = 109.133 (1)°	Block, colourless
γ = 108.604 (1)°	0.24 × 0.21 × 0.18 mm
V = 1487.79 (19) Å^3

Data collection

Bruker SMART APEX diffractometer	5455 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 28.0°, θmin = 1.7°
ω scans	h = −13→13
17008 measured reflections	k = −16→15
6766 independent reflections	l = −16→16

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0721P)^2 + 0.3938P] where P = (Fo^2 + 2Fc^2)/3
6766 reflections	(Δ/σ)max < 0.001
380 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.15 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
S1	0.19372 (5)	0.41194 (4)	0.12184 (3)	0.04269 (13)
N1	0.40420 (16)	0.67698 (13)	0.38393 (13)	0.0489 (4)
N2	0.14426 (17)	0.69014 (14)	0.15079 (13)	0.0482 (4)
H2	0.1176	0.7189	0.0936	0.058*
N3	0.07589 (15)	0.31049 (12)	0.25000 (11)	0.0381 (3)
N4	−0.05634 (15)	0.23108 (13)	0.05932 (12)	0.0409 (3)
O1	0.34944 (15)	0.67744 (13)	0.13894 (13)	0.0570 (4)
O2	0.23173 (15)	0.41153 (11)	0.42319 (10)	0.0500 (3)
C1	0.5154 (2)	0.64336 (17)	0.36568 (18)	0.0511 (5)
H1A	0.5995	0.6665	0.4332	0.061*
H1B	0.5428	0.6794	0.3095	0.061*
C2	0.44493 (19)	0.50845 (16)	0.32729 (16)	0.0445 (4)
H2A	0.4551	0.4770	0.3943	0.053*
C3	0.28026 (18)	0.48449 (14)	0.26859 (13)	0.0376 (4)
C4	0.27098 (18)	0.61112 (14)	0.28897 (14)	0.0385 (4)
C5	0.4388 (3)	0.8043 (2)	0.4120 (3)	0.0787 (8)
H5A	0.5222	0.8390	0.4790	0.118*
H5B	0.3595	0.8185	0.4221	0.118*
H5C	0.4575	0.8393	0.3534	0.118*
C6	0.5144 (2)	0.45240 (18)	0.26613 (18)	0.0537 (5)
C7	0.5314 (2)	0.4841 (2)	0.1720 (2)	0.0666 (6)
H7	0.4964	0.5401	0.1429	0.080*
C8	0.6010 (3)	0.4327 (3)	0.1203 (3)	0.0903 (9)
H8	0.6117	0.4542	0.0567	0.108*
C9	0.6529 (3)	0.3517 (3)	0.1624 (4)	0.1113 (14)
H9	0.6981	0.3171	0.1271	0.134*
C10	0.6391 (4)	0.3208 (3)	0.2558 (4)	0.1088 (12)
H10	0.6770	0.2663	0.2849	0.131*
C11	0.5691 (3)	0.3696 (2)	0.3085 (3)	0.0797 (8)
H11	0.5589	0.3469	0.3719	0.096*
C12	0.19665 (19)	0.40078 (14)	0.32454 (14)	0.0392 (4)
C13	0.05267 (18)	0.30452 (14)	0.13967 (13)	0.0366 (3)
C14	−0.01174 (18)	0.21457 (15)	0.28707 (14)	0.0385 (4)
H14	−0.0376	0.2509	0.3429	0.046*
C15	−0.14837 (18)	0.13934 (15)	0.19057 (14)	0.0392 (4)
C16	−0.2603 (2)	0.05052 (17)	0.21974 (17)	0.0486 (4)
H16A	−0.3532	0.0518	0.1769	0.058*
H16B	−0.2418	0.0771	0.2969	0.058*
C17	−0.2698 (3)	−0.07875 (18)	0.20138 (19)	0.0594 (5)
H17A	−0.1742	−0.0786	0.2373	0.071*
H17B	−0.3283	−0.1212	0.2390	0.071*
C18	−0.3299 (3)	−0.14950 (19)	0.0829 (2)	0.0678 (6)
H18A	−0.3484	−0.2325	0.0847	0.081*
H18B	−0.4213	−0.1431	0.0443	0.081*
C19	−0.2368 (3)	−0.1134 (2)	0.0160 (2)	0.0741 (7)
H19A	−0.2414	−0.1849	−0.0267	0.089*
H19B	−0.1383	−0.0721	0.0668	0.089*
C20	−0.2765 (3)	−0.0341 (2)	−0.06292 (19)	0.0712 (7)
H20A	−0.2025	−0.0072	−0.0927	0.085*
H20B	−0.3652	−0.0815	−0.1241	0.085*
C21	−0.2948 (2)	0.07387 (18)	−0.01134 (16)	0.0533 (5)
H21A	−0.3150	0.1207	−0.0660	0.064*
H21B	−0.3762	0.0476	0.0107	0.064*
C22	−0.16451 (18)	0.14988 (15)	0.08690 (14)	0.0402 (4)
C23	0.07304 (19)	0.14129 (15)	0.33949 (14)	0.0411 (4)
C24	0.0944 (2)	0.12927 (19)	0.44586 (17)	0.0563 (5)
H24	0.0637	0.1716	0.4887	0.068*
C25	0.1615 (3)	0.0543 (2)	0.4898 (2)	0.0719 (7)
H25	0.1755	0.0464	0.5619	0.086*
C26	0.2070 (3)	−0.0077 (2)	0.4280 (2)	0.0735 (7)
H26	0.2499	−0.0593	0.4573	0.088*
C27	0.1901 (3)	0.0055 (2)	0.3235 (2)	0.0711 (6)
H27	0.2231	−0.0358	0.2819	0.085*
C28	0.1235 (2)	0.0805 (2)	0.27876 (18)	0.0590 (5)
H28	0.1129	0.0899	0.2074	0.071*
C29	0.13983 (19)	0.61936 (15)	0.30553 (15)	0.0406 (4)
C30	0.0911 (2)	0.59898 (18)	0.38983 (17)	0.0533 (5)
H30	0.1387	0.5708	0.4480	0.064*
C31	−0.0304 (3)	0.6213 (2)	0.3862 (2)	0.0627 (6)
H31	−0.0653	0.6066	0.4419	0.075*
C32	−0.0994 (2)	0.6650 (2)	0.3012 (2)	0.0644 (6)
H32	−0.1808	0.6789	0.3001	0.077*
C33	−0.0508 (2)	0.6884 (2)	0.21768 (19)	0.0580 (5)
H33	−0.0974	0.7184	0.1606	0.070*
C34	0.06973 (19)	0.66598 (16)	0.22166 (15)	0.0438 (4)
C35	0.26298 (19)	0.66286 (15)	0.18298 (15)	0.0425 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0440 (2)	0.0422 (2)	0.0350 (2)	0.00756 (18)	0.01448 (18)	0.00928 (17)
N1	0.0436 (8)	0.0397 (8)	0.0523 (9)	0.0149 (7)	0.0075 (7)	0.0007 (7)
N2	0.0500 (9)	0.0552 (9)	0.0476 (9)	0.0262 (8)	0.0183 (7)	0.0253 (7)
N3	0.0436 (8)	0.0347 (7)	0.0337 (7)	0.0120 (6)	0.0133 (6)	0.0112 (6)
N4	0.0402 (8)	0.0419 (8)	0.0370 (7)	0.0122 (6)	0.0123 (6)	0.0121 (6)
O1	0.0574 (8)	0.0632 (9)	0.0701 (9)	0.0285 (7)	0.0373 (8)	0.0338 (7)
O2	0.0646 (8)	0.0434 (7)	0.0335 (6)	0.0146 (6)	0.0129 (6)	0.0106 (5)
C1	0.0380 (9)	0.0462 (10)	0.0572 (11)	0.0140 (8)	0.0067 (8)	0.0047 (9)
C2	0.0416 (9)	0.0425 (9)	0.0457 (10)	0.0184 (8)	0.0089 (8)	0.0106 (8)
C3	0.0406 (9)	0.0348 (8)	0.0339 (8)	0.0141 (7)	0.0094 (7)	0.0090 (6)
C4	0.0382 (8)	0.0349 (8)	0.0415 (9)	0.0136 (7)	0.0129 (7)	0.0116 (7)
C5	0.0610 (14)	0.0452 (12)	0.106 (2)	0.0149 (10)	0.0146 (14)	−0.0111 (12)
C6	0.0402 (10)	0.0489 (11)	0.0621 (13)	0.0179 (8)	0.0090 (9)	0.0006 (9)
C7	0.0501 (12)	0.0784 (15)	0.0661 (14)	0.0244 (11)	0.0186 (11)	0.0020 (12)
C8	0.0569 (15)	0.114 (2)	0.0796 (18)	0.0220 (15)	0.0217 (13)	−0.0204 (17)
C9	0.0705 (18)	0.112 (3)	0.126 (3)	0.0476 (19)	0.012 (2)	−0.044 (2)
C10	0.097 (2)	0.086 (2)	0.134 (3)	0.0622 (19)	0.014 (2)	−0.010 (2)
C11	0.0713 (15)	0.0606 (14)	0.101 (2)	0.0384 (13)	0.0142 (14)	0.0060 (13)
C12	0.0458 (9)	0.0342 (8)	0.0369 (9)	0.0162 (7)	0.0126 (7)	0.0107 (7)
C13	0.0401 (9)	0.0366 (8)	0.0358 (8)	0.0166 (7)	0.0141 (7)	0.0124 (7)
C14	0.0448 (9)	0.0384 (8)	0.0372 (8)	0.0168 (7)	0.0190 (7)	0.0127 (7)
C15	0.0393 (9)	0.0368 (8)	0.0440 (9)	0.0165 (7)	0.0155 (7)	0.0124 (7)
C16	0.0460 (10)	0.0497 (10)	0.0529 (11)	0.0153 (8)	0.0233 (9)	0.0157 (9)
C17	0.0637 (13)	0.0451 (11)	0.0646 (13)	0.0117 (9)	0.0246 (11)	0.0198 (10)
C18	0.0727 (15)	0.0435 (11)	0.0746 (15)	0.0138 (10)	0.0207 (12)	0.0089 (10)
C19	0.0888 (18)	0.0560 (13)	0.0749 (16)	0.0277 (13)	0.0316 (14)	−0.0024 (12)
C20	0.0738 (15)	0.0670 (14)	0.0509 (12)	0.0079 (12)	0.0184 (11)	−0.0024 (11)
C21	0.0426 (10)	0.0550 (11)	0.0474 (10)	0.0079 (9)	0.0071 (8)	0.0160 (9)
C22	0.0378 (9)	0.0394 (9)	0.0424 (9)	0.0151 (7)	0.0125 (7)	0.0121 (7)
C23	0.0423 (9)	0.0366 (8)	0.0410 (9)	0.0124 (7)	0.0128 (7)	0.0122 (7)
C24	0.0714 (14)	0.0547 (11)	0.0452 (10)	0.0250 (10)	0.0214 (10)	0.0186 (9)
C25	0.0860 (17)	0.0770 (16)	0.0564 (13)	0.0370 (14)	0.0198 (12)	0.0345 (12)
C26	0.0748 (16)	0.0638 (14)	0.0851 (18)	0.0372 (13)	0.0187 (14)	0.0330 (13)
C27	0.0773 (16)	0.0731 (15)	0.0790 (16)	0.0477 (13)	0.0289 (13)	0.0209 (13)
C28	0.0711 (14)	0.0704 (14)	0.0544 (12)	0.0430 (12)	0.0284 (11)	0.0235 (10)
C29	0.0417 (9)	0.0359 (8)	0.0438 (9)	0.0140 (7)	0.0161 (7)	0.0089 (7)
C30	0.0661 (13)	0.0494 (11)	0.0514 (11)	0.0228 (10)	0.0289 (10)	0.0136 (9)
C31	0.0697 (14)	0.0583 (12)	0.0693 (14)	0.0195 (11)	0.0431 (12)	0.0086 (11)
C32	0.0473 (11)	0.0675 (14)	0.0808 (16)	0.0230 (10)	0.0283 (11)	0.0056 (12)
C33	0.0459 (11)	0.0634 (13)	0.0628 (13)	0.0256 (10)	0.0138 (10)	0.0119 (10)
C34	0.0404 (9)	0.0423 (9)	0.0453 (10)	0.0147 (8)	0.0127 (8)	0.0095 (8)
C35	0.0441 (9)	0.0365 (9)	0.0479 (10)	0.0146 (7)	0.0174 (8)	0.0153 (7)

Geometric parameters (Å, º)

S1—C13	1.7469 (17)	C15—C22	1.340 (2)
S1—C3	1.8316 (17)	C15—C16	1.512 (2)
N1—C1	1.450 (2)	C16—C17	1.536 (3)
N1—C5	1.455 (3)	C16—H16A	0.970
N1—C4	1.463 (2)	C16—H16B	0.970
N2—C35	1.352 (2)	C17—C18	1.526 (3)
N2—C34	1.403 (2)	C17—H17A	0.970
N2—H2	0.860	C17—H17B	0.970
N3—C12	1.377 (2)	C18—C19	1.520 (4)
N3—C13	1.380 (2)	C18—H18A	0.970
N3—C14	1.476 (2)	C18—H18B	0.970
N4—C13	1.274 (2)	C19—C20	1.531 (4)
N4—C22	1.430 (2)	C19—H19A	0.970
O1—C35	1.215 (2)	C19—H19B	0.970
O2—C12	1.208 (2)	C20—C21	1.521 (3)
C1—C2	1.527 (3)	C20—H20A	0.970
C1—H1A	0.970	C20—H20B	0.970
C1—H1B	0.970	C21—C22	1.495 (3)
C2—C6	1.506 (3)	C21—H21A	0.970
C2—C3	1.580 (2)	C21—H21B	0.970
C2—H2A	0.980	C23—C24	1.371 (3)
C3—C12	1.536 (2)	C23—C28	1.378 (3)
C3—C4	1.581 (2)	C24—C25	1.386 (3)
C4—C29	1.513 (2)	C24—H24	0.930
C4—C35	1.569 (2)	C25—C26	1.357 (4)
C5—H5A	0.960	C25—H25	0.930
C5—H5B	0.960	C26—C27	1.356 (4)
C5—H5C	0.960	C26—H26	0.930
C6—C7	1.380 (3)	C27—C28	1.385 (3)
C6—C11	1.389 (3)	C27—H27	0.930
C7—C8	1.396 (4)	C28—H28	0.930
C7—H7	0.930	C29—C30	1.379 (3)
C8—C9	1.353 (5)	C29—C34	1.393 (2)
C8—H8	0.930	C30—C31	1.391 (3)
C9—C10	1.356 (5)	C30—H30	0.930
C9—H9	0.930	C31—C32	1.375 (3)
C10—C11	1.392 (4)	C31—H31	0.930
C10—H10	0.930	C32—C33	1.375 (3)
C11—H11	0.930	C32—H32	0.930
C14—C15	1.513 (2)	C33—C34	1.379 (3)
C14—C23	1.518 (2)	C33—H33	0.930
C14—H14	0.980
C13—S1—C3	93.35 (8)	C17—C16—H16A	108.1
C1—N1—C5	114.99 (17)	C15—C16—H16B	108.1
C1—N1—C4	107.07 (14)	C17—C16—H16B	108.1
C5—N1—C4	115.13 (16)	H16A—C16—H16B	107.3
C35—N2—C34	111.99 (15)	C18—C17—C16	118.06 (18)
C35—N2—H2	124.0	C18—C17—H17A	107.8
C34—N2—H2	124.0	C16—C17—H17A	107.8
C12—N3—C13	116.89 (14)	C18—C17—H17B	107.8
C12—N3—C14	121.07 (13)	C16—C17—H17B	107.8
C13—N3—C14	121.40 (14)	H17A—C17—H17B	107.1
C13—N4—C22	116.56 (14)	C19—C18—C17	116.5 (2)
N1—C1—C2	103.34 (15)	C19—C18—H18A	108.2
N1—C1—H1A	111.1	C17—C18—H18A	108.2
C2—C1—H1A	111.1	C19—C18—H18B	108.2
N1—C1—H1B	111.1	C17—C18—H18B	108.2
C2—C1—H1B	111.1	H18A—C18—H18B	107.3
H1A—C1—H1B	109.1	C18—C19—C20	115.7 (2)
C6—C2—C1	114.95 (17)	C18—C19—H19A	108.4
C6—C2—C3	118.39 (15)	C20—C19—H19A	108.4
C1—C2—C3	104.04 (14)	C18—C19—H19B	108.4
C6—C2—H2A	106.2	C20—C19—H19B	108.4
C1—C2—H2A	106.2	H19A—C19—H19B	107.4
C3—C2—H2A	106.2	C21—C20—C19	114.84 (18)
C12—C3—C2	108.75 (13)	C21—C20—H20A	108.6
C12—C3—C4	110.72 (13)	C19—C20—H20A	108.6
C2—C3—C4	104.23 (13)	C21—C20—H20B	108.6
C12—C3—S1	104.64 (11)	C19—C20—H20B	108.6
C2—C3—S1	117.26 (12)	H20A—C20—H20B	107.5
C4—C3—S1	111.28 (11)	C22—C21—C20	112.25 (17)
N1—C4—C29	113.17 (14)	C22—C21—H21A	109.2
N1—C4—C35	113.22 (14)	C20—C21—H21A	109.2
C29—C4—C35	101.40 (13)	C22—C21—H21B	109.2
N1—C4—C3	101.96 (13)	C20—C21—H21B	109.2
C29—C4—C3	118.39 (14)	H21A—C21—H21B	107.9
C35—C4—C3	109.11 (13)	C15—C22—N4	123.28 (16)
N1—C5—H5A	109.5	C15—C22—C21	123.07 (16)
N1—C5—H5B	109.5	N4—C22—C21	113.59 (15)
H5A—C5—H5B	109.5	C24—C23—C28	118.80 (18)
N1—C5—H5C	109.5	C24—C23—C14	120.79 (17)
H5A—C5—H5C	109.5	C28—C23—C14	120.33 (16)
H5B—C5—H5C	109.5	C23—C24—C25	120.3 (2)
C7—C6—C11	118.6 (2)	C23—C24—H24	119.9
C7—C6—C2	122.35 (19)	C25—C24—H24	119.9
C11—C6—C2	119.0 (2)	C26—C25—C24	120.3 (2)
C6—C7—C8	120.3 (3)	C26—C25—H25	119.8
C6—C7—H7	119.9	C24—C25—H25	119.8
C8—C7—H7	119.9	C27—C26—C25	120.2 (2)
C9—C8—C7	120.3 (3)	C27—C26—H26	119.9
C9—C8—H8	119.9	C25—C26—H26	119.9
C7—C8—H8	119.9	C26—C27—C28	120.1 (2)
C8—C9—C10	120.3 (3)	C26—C27—H27	120.0
C8—C9—H9	119.9	C28—C27—H27	120.0
C10—C9—H9	119.9	C23—C28—C27	120.3 (2)
C9—C10—C11	120.7 (3)	C23—C28—H28	119.8
C9—C10—H10	119.6	C27—C28—H28	119.8
C11—C10—H10	119.6	C30—C29—C34	119.33 (17)
C6—C11—C10	119.7 (3)	C30—C29—C4	131.53 (17)
C6—C11—H11	120.1	C34—C29—C4	108.87 (15)
C10—C11—H11	120.1	C29—C30—C31	118.8 (2)
O2—C12—N3	122.82 (16)	C29—C30—H30	120.6
O2—C12—C3	124.38 (16)	C31—C30—H30	120.6
N3—C12—C3	112.80 (14)	C32—C31—C30	120.7 (2)
N4—C13—N3	125.61 (15)	C32—C31—H31	119.7
N4—C13—S1	123.01 (13)	C30—C31—H31	119.7
N3—C13—S1	111.38 (12)	C31—C32—C33	121.4 (2)
N3—C14—C15	109.41 (13)	C31—C32—H32	119.3
N3—C14—C23	110.61 (14)	C33—C32—H32	119.3
C15—C14—C23	111.99 (14)	C32—C33—C34	117.6 (2)
N3—C14—H14	108.2	C32—C33—H33	121.2
C15—C14—H14	108.2	C34—C33—H33	121.2
C23—C14—H14	108.2	C33—C34—C29	122.07 (18)
C22—C15—C16	123.46 (16)	C33—C34—N2	127.89 (18)
C22—C15—C14	121.18 (15)	C29—C34—N2	109.95 (15)
C16—C15—C14	115.33 (15)	O1—C35—N2	126.23 (17)
C15—C16—C17	116.82 (16)	O1—C35—C4	125.98 (16)
C15—C16—H16A	108.1	N2—C35—C4	107.77 (15)
C5—N1—C1—C2	−174.62 (19)	C12—N3—C14—C23	−64.8 (2)
C4—N1—C1—C2	−45.33 (19)	C13—N3—C14—C23	105.68 (17)
N1—C1—C2—C6	160.19 (16)	N3—C14—C15—C22	12.0 (2)
N1—C1—C2—C3	29.13 (19)	C23—C14—C15—C22	−110.99 (18)
C6—C2—C3—C12	107.94 (18)	N3—C14—C15—C16	−169.98 (14)
C1—C2—C3—C12	−123.06 (16)	C23—C14—C15—C16	67.00 (19)
C6—C2—C3—C4	−133.92 (17)	C22—C15—C16—C17	77.9 (2)
C1—C2—C3—C4	−4.92 (18)	C14—C15—C16—C17	−100.1 (2)
C6—C2—C3—S1	−10.4 (2)	C15—C16—C17—C18	−70.9 (3)
C1—C2—C3—S1	118.57 (14)	C16—C17—C18—C19	70.1 (3)
C13—S1—C3—C12	8.80 (12)	C17—C18—C19—C20	−99.4 (3)
C13—S1—C3—C2	129.36 (13)	C18—C19—C20—C21	49.9 (3)
C13—S1—C3—C4	−110.81 (12)	C19—C20—C21—C22	56.0 (3)
C1—N1—C4—C29	169.38 (15)	C16—C15—C22—N4	−177.69 (16)
C5—N1—C4—C29	−61.4 (2)	C14—C15—C22—N4	0.1 (3)
C1—N1—C4—C35	−75.95 (18)	C16—C15—C22—C21	−0.6 (3)
C5—N1—C4—C35	53.3 (2)	C14—C15—C22—C21	177.23 (16)
C1—N1—C4—C3	41.12 (17)	C13—N4—C22—C15	−7.8 (2)
C5—N1—C4—C3	170.33 (18)	C13—N4—C22—C21	174.82 (16)
C12—C3—C4—N1	96.19 (15)	C20—C21—C22—C15	−94.1 (2)
C2—C3—C4—N1	−20.59 (16)	C20—C21—C22—N4	83.2 (2)
S1—C3—C4—N1	−147.88 (12)	N3—C14—C23—C24	122.10 (18)
C12—C3—C4—C29	−28.7 (2)	C15—C14—C23—C24	−115.56 (19)
C2—C3—C4—C29	−145.45 (15)	N3—C14—C23—C28	−61.3 (2)
S1—C3—C4—C29	87.26 (16)	C15—C14—C23—C28	61.0 (2)
C12—C3—C4—C35	−143.82 (14)	C28—C23—C24—C25	−2.0 (3)
C2—C3—C4—C35	99.40 (15)	C14—C23—C24—C25	174.6 (2)
S1—C3—C4—C35	−27.89 (16)	C23—C24—C25—C26	0.2 (4)
C1—C2—C6—C7	−57.1 (3)	C24—C25—C26—C27	1.5 (4)
C3—C2—C6—C7	66.7 (3)	C25—C26—C27—C28	−1.3 (4)
C1—C2—C6—C11	120.0 (2)	C24—C23—C28—C27	2.2 (3)
C3—C2—C6—C11	−116.3 (2)	C14—C23—C28—C27	−174.4 (2)
C11—C6—C7—C8	0.7 (3)	C26—C27—C28—C23	−0.6 (4)
C2—C6—C7—C8	177.7 (2)	N1—C4—C29—C30	−51.4 (3)
C6—C7—C8—C9	−0.3 (4)	C35—C4—C29—C30	−173.02 (19)
C7—C8—C9—C10	−0.7 (5)	C3—C4—C29—C30	67.7 (3)
C8—C9—C10—C11	1.4 (5)	N1—C4—C29—C34	122.43 (16)
C7—C6—C11—C10	−0.1 (4)	C35—C4—C29—C34	0.85 (18)
C2—C6—C11—C10	−177.2 (2)	C3—C4—C29—C34	−118.40 (16)
C9—C10—C11—C6	−1.0 (5)	C34—C29—C30—C31	2.5 (3)
C13—N3—C12—O2	−176.36 (16)	C4—C29—C30—C31	175.86 (19)
C14—N3—C12—O2	−5.4 (3)	C29—C30—C31—C32	−1.1 (3)
C13—N3—C12—C3	3.5 (2)	C30—C31—C32—C33	−0.3 (4)
C14—N3—C12—C3	174.41 (14)	C31—C32—C33—C34	0.4 (3)
C2—C3—C12—O2	45.3 (2)	C32—C33—C34—C29	1.0 (3)
C4—C3—C12—O2	−68.6 (2)	C32—C33—C34—N2	−175.3 (2)
S1—C3—C12—O2	171.39 (15)	C30—C29—C34—C33	−2.5 (3)
C2—C3—C12—N3	−134.50 (15)	C4—C29—C34—C33	−177.26 (17)
C4—C3—C12—N3	111.54 (15)	C30—C29—C34—N2	174.40 (17)
S1—C3—C12—N3	−8.44 (16)	C4—C29—C34—N2	−0.3 (2)
C22—N4—C13—N3	1.3 (2)	C35—N2—C34—C33	176.25 (19)
C22—N4—C13—S1	−178.77 (12)	C35—N2—C34—C29	−0.4 (2)
C12—N3—C13—N4	−176.33 (16)	C34—N2—C35—O1	−177.94 (19)
C14—N3—C13—N4	12.8 (2)	C34—N2—C35—C4	1.0 (2)
C12—N3—C13—S1	3.76 (18)	N1—C4—C35—O1	56.3 (2)
C14—N3—C13—S1	−167.14 (12)	C29—C4—C35—O1	177.83 (18)
C3—S1—C13—N4	172.45 (15)	C3—C4—C35—O1	−56.5 (2)
C3—S1—C13—N3	−7.64 (13)	N1—C4—C35—N2	−122.65 (16)
C12—N3—C14—C15	171.33 (14)	C29—C4—C35—N2	−1.11 (18)
C13—N3—C14—C15	−18.2 (2)	C3—C4—C35—N2	124.57 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1	0.97	2.49	3.069 (3)	118
C2—H2A···O2	0.98	2.42	2.927 (2)	112
C30—H30···O2	0.93	2.48	3.094 (2)	123
N2—H2···N4^i	0.86	2.11	2.965 (2)	172

Symmetry code: (i) −x, −y+1, −z.