1′-Methyl-5-diphenyl-4′-p-tolyl-5,6,7,8,9,10-hexahydro-1,3-cyclooctapyrimidino[2,3-b]thiazole-2-spiro-3′-pyrrolidine-2′-spiro-3′′-1H-indole-2′′,3(2H,3′′H)-dione

The pyrrolidine ring in the title compound, C₃₆H₃₆N₄O₂S, adopts an envelope conformation. The thia­zolidine ring adopts a twisted conformation, with a pseudo-twofold axis passing through the N atom and the opposite S—C bond. The crystal packing is stabilized by N—H...N inter­molecular inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.104
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



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
   0 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
   0 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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1-N-methyl-spiro[2.3']oxindole-spiro[3.2'']-5''-phenyl- 5'',6'',7'',8'',9'',10'',11''-heptahydrocycloocteno[1,2-d]thiazolo[3,2-a] pyrimidin-3''-one-4-(p-methyl)phenyl-pyrrolidine

Crystal data

C36H36N4O2S	Z = 2
Mr = 588.75	F(000) = 624
Triclinic, P1	Dx = 1.272 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.3531 (8) Å	Cell parameters from 2615 reflections
b = 12.1973 (9) Å	θ = 1.7–25.0°
c = 13.2117 (9) Å	µ = 0.15 mm^−1
α = 94.181 (1)°	T = 293 K
β = 111.683 (1)°	Block, colourless
γ = 111.377 (1)°	0.25 × 0.22 × 0.20 mm
V = 1536.88 (19) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4781 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 25.0°, θmin = 1.7°
ω scans	h = −13→13
14952 measured reflections	k = −14→14
5422 independent reflections	l = −15→15

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0549P)^2 + 0.3799P] where P = (Fo^2 + 2Fc^2)/3
5422 reflections	(Δ/σ)max = 0.001
388 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.17 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
C1	0.73326 (15)	0.37958 (13)	0.19950 (12)	0.0373 (3)
C2	0.72911 (15)	0.50675 (13)	0.22412 (11)	0.0362 (3)
C3	0.56902 (15)	0.47880 (14)	0.16187 (12)	0.0413 (3)
H3	0.5591	0.5145	0.0968	0.050*
C4	0.49593 (16)	0.34152 (14)	0.11520 (14)	0.0471 (4)
H4A	0.4674	0.3004	0.1679	0.056*
H4B	0.4144	0.3190	0.0446	0.056*
C5	0.5637 (2)	0.18323 (16)	0.06591 (18)	0.0680 (5)
H5A	0.4771	0.1467	−0.0005	0.102*
H5B	0.5529	0.1459	0.1253	0.102*
H5C	0.6357	0.1719	0.0510	0.102*
C6	0.74057 (16)	0.32337 (13)	0.30323 (13)	0.0406 (3)
C7	0.92601 (15)	0.32897 (14)	0.26988 (13)	0.0429 (4)
C8	1.03965 (17)	0.30851 (16)	0.27468 (16)	0.0555 (4)
H8	1.0852	0.2786	0.3322	0.067*
C9	1.08325 (19)	0.33402 (17)	0.19098 (17)	0.0611 (5)
H9	1.1600	0.3217	0.1926	0.073*
C10	1.0153 (2)	0.37745 (17)	0.10500 (17)	0.0598 (5)
H10	1.0460	0.3929	0.0491	0.072*
C11	0.90165 (18)	0.39834 (15)	0.10127 (14)	0.0499 (4)
H11	0.8555	0.4270	0.0430	0.060*
C12	0.85822 (15)	0.37585 (13)	0.18543 (12)	0.0397 (3)
C13	0.81039 (15)	0.59629 (13)	0.17241 (12)	0.0373 (3)
C14	1.01341 (15)	0.79227 (13)	0.21776 (12)	0.0374 (3)
H14	1.0375	0.7580	0.1629	0.045*
C15	0.93133 (15)	0.86236 (13)	0.16265 (12)	0.0396 (3)
C16	0.90523 (19)	0.87183 (16)	0.05408 (14)	0.0538 (4)
H16	0.9320	0.8299	0.0117	0.065*
C17	0.8392 (2)	0.9436 (2)	0.00762 (18)	0.0697 (6)
H17	0.8224	0.9497	−0.0657	0.084*
C18	0.7990 (2)	1.00510 (19)	0.0681 (2)	0.0706 (6)
H18	0.7571	1.0549	0.0370	0.085*
C19	0.8203 (2)	0.99351 (19)	0.17514 (19)	0.0695 (5)
H19	0.7903	1.0335	0.2160	0.083*
C20	0.8864 (2)	0.92245 (17)	0.22225 (16)	0.0568 (4)
H20	0.9008	0.9151	0.2949	0.068*
C21	1.14770 (15)	0.87242 (13)	0.31928 (12)	0.0390 (3)
C22	1.25901 (18)	0.96331 (16)	0.29344 (15)	0.0532 (4)
H22A	1.2394	0.9346	0.2160	0.064*
H22B	1.3483	0.9638	0.3402	0.064*
C23	1.2749 (2)	1.09413 (17)	0.30986 (17)	0.0692 (6)
H23A	1.3323	1.1368	0.2738	0.083*
H23B	1.1831	1.0927	0.2705	0.083*
C24	1.3381 (3)	1.16800 (18)	0.43020 (19)	0.0835 (7)
H24A	1.4253	1.1625	0.4719	0.100*
H24B	1.3604	1.2524	0.4286	0.100*
C25	1.2480 (3)	1.13147 (19)	0.4940 (2)	0.0843 (7)
H25A	1.1511	1.0877	0.4399	0.101*
H25B	1.2562	1.2047	0.5358	0.101*
C26	1.2828 (3)	1.05319 (19)	0.57546 (17)	0.0764 (6)
H26A	1.3710	1.1031	0.6392	0.092*
H26B	1.2114	1.0262	0.6031	0.092*
C27	1.29348 (18)	0.94261 (15)	0.52607 (14)	0.0536 (4)
H27A	1.3728	0.9692	0.5074	0.064*
H27B	1.3103	0.8962	0.5821	0.064*
C28	1.16407 (15)	0.86221 (13)	0.42292 (12)	0.0397 (3)
C29	0.95252 (15)	0.69647 (12)	0.36236 (11)	0.0348 (3)
C30	0.50355 (16)	0.52715 (14)	0.22366 (13)	0.0432 (4)
C31	0.45051 (19)	0.60976 (16)	0.18534 (15)	0.0546 (4)
H31	0.4631	0.6401	0.1257	0.065*
C32	0.3790 (2)	0.64755 (17)	0.23486 (17)	0.0639 (5)
H32	0.3445	0.7031	0.2077	0.077*
C33	0.35758 (18)	0.60505 (17)	0.32325 (16)	0.0580 (5)
C34	0.41248 (17)	0.52470 (17)	0.36271 (15)	0.0544 (4)
H34	0.4012	0.4959	0.4233	0.065*
C35	0.48412 (17)	0.48577 (16)	0.31415 (14)	0.0492 (4)
H35	0.5197	0.4313	0.3424	0.059*
C36	0.2724 (2)	0.6404 (2)	0.3724 (2)	0.0838 (7)
H36A	0.2417	0.6957	0.3343	0.126*
H36B	0.3286	0.6787	0.4508	0.126*
H36C	0.1925	0.5692	0.3634	0.126*
N1	0.60246 (13)	0.31249 (11)	0.09923 (11)	0.0442 (3)
N2	0.85541 (14)	0.30023 (12)	0.33853 (11)	0.0463 (3)
H2	0.8818	0.2714	0.3961	0.056*
N3	0.92813 (12)	0.69128 (10)	0.25142 (9)	0.0361 (3)
N4	1.05886 (13)	0.77548 (11)	0.44664 (10)	0.0386 (3)
O1	0.65631 (13)	0.30230 (11)	0.34333 (10)	0.0533 (3)
O2	0.77502 (12)	0.58628 (10)	0.07285 (8)	0.0487 (3)
S1	0.81743 (4)	0.57869 (3)	0.37473 (3)	0.04136 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0375 (8)	0.0339 (7)	0.0364 (8)	0.0128 (6)	0.0134 (6)	0.0096 (6)
C2	0.0383 (8)	0.0340 (7)	0.0307 (7)	0.0133 (6)	0.0109 (6)	0.0088 (6)
C3	0.0390 (8)	0.0421 (8)	0.0359 (8)	0.0163 (7)	0.0095 (6)	0.0108 (6)
C4	0.0362 (8)	0.0453 (9)	0.0476 (9)	0.0141 (7)	0.0095 (7)	0.0058 (7)
C5	0.0527 (11)	0.0453 (10)	0.0819 (14)	0.0144 (9)	0.0144 (10)	−0.0087 (9)
C6	0.0440 (8)	0.0341 (7)	0.0420 (8)	0.0146 (7)	0.0177 (7)	0.0125 (6)
C7	0.0383 (8)	0.0396 (8)	0.0430 (8)	0.0135 (7)	0.0125 (7)	0.0080 (7)
C8	0.0442 (9)	0.0554 (10)	0.0587 (11)	0.0233 (8)	0.0121 (8)	0.0088 (8)
C9	0.0439 (9)	0.0581 (11)	0.0754 (13)	0.0182 (8)	0.0255 (9)	0.0007 (9)
C10	0.0597 (11)	0.0556 (11)	0.0660 (12)	0.0165 (9)	0.0379 (10)	0.0075 (9)
C11	0.0554 (10)	0.0477 (9)	0.0467 (9)	0.0183 (8)	0.0250 (8)	0.0120 (7)
C12	0.0377 (8)	0.0350 (7)	0.0399 (8)	0.0115 (6)	0.0139 (6)	0.0071 (6)
C13	0.0427 (8)	0.0332 (7)	0.0340 (8)	0.0160 (6)	0.0140 (6)	0.0097 (6)
C14	0.0437 (8)	0.0356 (7)	0.0355 (7)	0.0154 (6)	0.0203 (6)	0.0113 (6)
C15	0.0382 (8)	0.0349 (7)	0.0390 (8)	0.0099 (6)	0.0145 (6)	0.0114 (6)
C16	0.0627 (11)	0.0535 (10)	0.0432 (9)	0.0220 (9)	0.0217 (8)	0.0188 (8)
C17	0.0723 (13)	0.0754 (13)	0.0573 (11)	0.0301 (11)	0.0204 (10)	0.0375 (10)
C18	0.0590 (12)	0.0624 (12)	0.0911 (16)	0.0309 (10)	0.0237 (11)	0.0395 (12)
C19	0.0712 (13)	0.0694 (13)	0.0852 (15)	0.0439 (11)	0.0362 (12)	0.0243 (11)
C20	0.0673 (11)	0.0652 (11)	0.0543 (10)	0.0383 (10)	0.0310 (9)	0.0234 (9)
C21	0.0390 (8)	0.0360 (8)	0.0417 (8)	0.0154 (6)	0.0169 (7)	0.0108 (6)
C22	0.0449 (9)	0.0568 (10)	0.0484 (9)	0.0111 (8)	0.0202 (8)	0.0134 (8)
C23	0.0731 (13)	0.0498 (10)	0.0606 (11)	0.0041 (9)	0.0238 (10)	0.0204 (9)
C24	0.1028 (17)	0.0400 (10)	0.0724 (14)	0.0048 (11)	0.0269 (13)	0.0093 (9)
C25	0.117 (2)	0.0484 (11)	0.0769 (15)	0.0310 (12)	0.0370 (14)	0.0020 (10)
C26	0.0913 (16)	0.0575 (12)	0.0505 (11)	0.0094 (11)	0.0241 (11)	−0.0023 (9)
C27	0.0452 (9)	0.0504 (10)	0.0430 (9)	0.0074 (8)	0.0081 (7)	0.0132 (8)
C28	0.0392 (8)	0.0355 (8)	0.0403 (8)	0.0144 (6)	0.0137 (7)	0.0110 (6)
C29	0.0396 (8)	0.0336 (7)	0.0326 (7)	0.0173 (6)	0.0143 (6)	0.0105 (6)
C30	0.0379 (8)	0.0405 (8)	0.0427 (8)	0.0166 (7)	0.0090 (7)	0.0076 (7)
C31	0.0601 (10)	0.0471 (9)	0.0537 (10)	0.0274 (8)	0.0163 (8)	0.0138 (8)
C32	0.0655 (12)	0.0518 (10)	0.0699 (12)	0.0370 (10)	0.0136 (10)	0.0071 (9)
C33	0.0464 (9)	0.0570 (11)	0.0566 (11)	0.0247 (8)	0.0086 (8)	−0.0081 (9)
C34	0.0460 (9)	0.0647 (11)	0.0492 (10)	0.0249 (9)	0.0166 (8)	0.0084 (8)
C35	0.0443 (9)	0.0556 (10)	0.0517 (9)	0.0271 (8)	0.0178 (8)	0.0171 (8)
C36	0.0720 (14)	0.0885 (16)	0.0897 (16)	0.0456 (13)	0.0275 (12)	−0.0093 (13)
N1	0.0388 (7)	0.0387 (7)	0.0429 (7)	0.0137 (6)	0.0091 (6)	0.0015 (6)
N2	0.0486 (8)	0.0500 (8)	0.0427 (7)	0.0241 (6)	0.0167 (6)	0.0221 (6)
N3	0.0411 (7)	0.0322 (6)	0.0304 (6)	0.0118 (5)	0.0138 (5)	0.0090 (5)
N4	0.0405 (7)	0.0370 (6)	0.0325 (6)	0.0133 (6)	0.0124 (5)	0.0092 (5)
O1	0.0604 (7)	0.0553 (7)	0.0607 (7)	0.0279 (6)	0.0368 (6)	0.0288 (6)
O2	0.0598 (7)	0.0423 (6)	0.0302 (6)	0.0125 (5)	0.0138 (5)	0.0096 (5)
S1	0.0432 (2)	0.0404 (2)	0.0314 (2)	0.00907 (17)	0.01483 (16)	0.00959 (15)

Geometric parameters (Å, º)

C1—N1	1.460 (2)	C18—H18	0.930
C1—C12	1.513 (2)	C19—C20	1.382 (3)
C1—C6	1.565 (2)	C19—H19	0.930
C1—C2	1.583 (2)	C20—H20	0.930
C2—C13	1.533 (2)	C21—C28	1.334 (2)
C2—C3	1.581 (2)	C21—C22	1.515 (2)
C2—S1	1.834 (1)	C22—C23	1.529 (3)
C3—C30	1.505 (2)	C22—H22A	0.970
C3—C4	1.527 (2)	C22—H22B	0.970
C3—H3	0.980	C23—C24	1.527 (3)
C4—N1	1.457 (2)	C23—H23A	0.970
C4—H4A	0.970	C23—H23B	0.970
C4—H4B	0.970	C24—C25	1.521 (3)
C5—N1	1.457 (2)	C24—H24A	0.970
C5—H5A	0.960	C24—H24B	0.970
C5—H5B	0.960	C25—C26	1.529 (3)
C5—H5C	0.960	C25—H25A	0.970
C6—O1	1.215 (2)	C25—H25B	0.970
C6—N2	1.355 (2)	C26—C27	1.520 (3)
C7—C8	1.381 (2)	C26—H26A	0.970
C7—C12	1.394 (2)	C26—H26B	0.970
C7—N2	1.403 (2)	C27—C28	1.501 (2)
C8—C9	1.381 (3)	C27—H27A	0.970
C8—H8	0.930	C27—H27B	0.970
C9—C10	1.380 (3)	C28—N4	1.431 (2)
C9—H9	0.930	C29—N4	1.276 (2)
C10—C11	1.389 (2)	C29—N3	1.380 (2)
C10—H10	0.930	C29—S1	1.748 (1)
C11—C12	1.380 (2)	C30—C31	1.388 (2)
C11—H11	0.930	C30—C35	1.391 (2)
C13—O2	1.207 (2)	C31—C32	1.386 (3)
C13—N3	1.372 (2)	C31—H31	0.930
C14—N3	1.477 (2)	C32—C33	1.378 (3)
C14—C21	1.513 (2)	C32—H32	0.930
C14—C15	1.516 (2)	C33—C34	1.379 (3)
C14—H14	0.980	C33—C36	1.506 (3)
C15—C16	1.376 (2)	C34—C35	1.386 (2)
C15—C20	1.379 (2)	C34—H34	0.930
C16—C17	1.386 (3)	C35—H35	0.930
C16—H16	0.930	C36—H36A	0.960
C17—C18	1.357 (3)	C36—H36B	0.960
C17—H17	0.930	C36—H36C	0.960
C18—C19	1.371 (3)	N2—H2	0.860
N1—C1—C12	112.57 (12)	C28—C21—C22	123.60 (14)
N1—C1—C6	113.62 (12)	C14—C21—C22	114.98 (13)
C12—C1—C6	101.38 (11)	C21—C22—C23	117.18 (15)
N1—C1—C2	101.99 (11)	C21—C22—H22A	108.0
C12—C1—C2	118.76 (12)	C23—C22—H22A	108.0
C6—C1—C2	108.96 (11)	C21—C22—H22B	108.0
C13—C2—C3	108.76 (11)	C23—C22—H22B	108.0
C13—C2—C1	110.60 (11)	H22A—C22—H22B	107.2
C3—C2—C1	104.26 (11)	C24—C23—C22	117.36 (17)
C13—C2—S1	104.63 (9)	C24—C23—H23A	108.0
C3—C2—S1	116.84 (10)	C22—C23—H23A	108.0
C1—C2—S1	111.79 (9)	C24—C23—H23B	108.0
C30—C3—C4	114.21 (13)	C22—C23—H23B	108.0
C30—C3—C2	119.05 (12)	H23A—C23—H23B	107.2
C4—C3—C2	104.19 (12)	C25—C24—C23	116.34 (19)
C30—C3—H3	106.2	C25—C24—H24A	108.2
C4—C3—H3	106.2	C23—C24—H24A	108.2
C2—C3—H3	106.2	C25—C24—H24B	108.2
N1—C4—C3	103.51 (12)	C23—C24—H24B	108.2
N1—C4—H4A	111.1	H24A—C24—H24B	107.4
C3—C4—H4A	111.1	C24—C25—C26	115.8 (2)
N1—C4—H4B	111.1	C24—C25—H25A	108.3
C3—C4—H4B	111.1	C26—C25—H25A	108.3
H4A—C4—H4B	109.0	C24—C25—H25B	108.3
N1—C5—H5A	109.5	C26—C25—H25B	108.3
N1—C5—H5B	109.5	H25A—C25—H25B	107.4
H5A—C5—H5B	109.5	C27—C26—C25	114.88 (16)
N1—C5—H5C	109.5	C27—C26—H26A	108.5
H5A—C5—H5C	109.5	C25—C26—H26A	108.5
H5B—C5—H5C	109.5	C27—C26—H26B	108.5
O1—C6—N2	126.30 (14)	C25—C26—H26B	108.5
O1—C6—C1	125.77 (14)	H26A—C26—H26B	107.5
N2—C6—C1	107.92 (12)	C28—C27—C26	112.73 (15)
C8—C7—C12	121.94 (15)	C28—C27—H27A	109.0
C8—C7—N2	128.01 (15)	C26—C27—H27A	109.0
C12—C7—N2	109.90 (13)	C28—C27—H27B	109.0
C9—C8—C7	117.59 (17)	C26—C27—H27B	109.0
C9—C8—H8	121.2	H27A—C27—H27B	107.8
C7—C8—H8	121.2	C21—C28—N4	123.29 (13)
C10—C9—C8	121.40 (17)	C21—C28—C27	123.16 (14)
C10—C9—H9	119.3	N4—C28—C27	113.54 (13)
C8—C9—H9	119.3	N4—C29—N3	125.67 (13)
C9—C10—C11	120.56 (17)	N4—C29—S1	123.16 (11)
C9—C10—H10	119.7	N3—C29—S1	111.17 (10)
C11—C10—H10	119.7	C31—C30—C35	117.54 (16)
C12—C11—C10	118.97 (17)	C31—C30—C3	119.72 (15)
C12—C11—H11	120.5	C35—C30—C3	122.56 (14)
C10—C11—H11	120.5	C32—C31—C30	120.78 (17)
C11—C12—C7	119.50 (15)	C32—C31—H31	119.6
C11—C12—C1	131.23 (14)	C30—C31—H31	119.6
C7—C12—C1	108.89 (13)	C33—C32—C31	121.74 (17)
O2—C13—N3	122.81 (13)	C33—C32—H32	119.1
O2—C13—C2	124.25 (13)	C31—C32—H32	119.1
N3—C13—C2	112.94 (12)	C32—C33—C34	117.51 (17)
N3—C14—C21	109.23 (11)	C32—C33—C36	121.64 (18)
N3—C14—C15	110.70 (12)	C34—C33—C36	120.8 (2)
C21—C14—C15	112.12 (12)	C33—C34—C35	121.54 (18)
N3—C14—H14	108.2	C33—C34—H34	119.2
C21—C14—H14	108.2	C35—C34—H34	119.2
C15—C14—H14	108.2	C34—C35—C30	120.87 (16)
C16—C15—C20	118.55 (15)	C34—C35—H35	119.6
C16—C15—C14	120.94 (14)	C30—C35—H35	119.6
C20—C15—C14	120.46 (14)	C33—C36—H36A	109.5
C15—C16—C17	120.29 (18)	C33—C36—H36B	109.5
C15—C16—H16	119.9	H36A—C36—H36B	109.5
C17—C16—H16	119.9	C33—C36—H36C	109.5
C18—C17—C16	120.68 (18)	H36A—C36—H36C	109.5
C18—C17—H17	119.7	H36B—C36—H36C	109.5
C16—C17—H17	119.7	C4—N1—C5	114.6 (1)
C17—C18—C19	119.67 (18)	C4—N1—C1	107.2 (1)
C17—C18—H18	120.2	C5—N1—C1	115.2 (1)
C19—C18—H18	120.2	C6—N2—C7	111.9 (1)
C18—C19—C20	120.01 (19)	C6—N2—H2	124.1
C18—C19—H19	120.0	C7—N2—H2	124.1
C20—C19—H19	120.0	C13—N3—C29	117.2 (1)
C15—C20—C19	120.74 (17)	C13—N3—C14	120.8 (1)
C15—C20—H20	119.6	C29—N3—C14	121.4 (1)
C19—C20—H20	119.6	C29—N4—C28	116.4 (1)
C28—C21—C14	121.43 (13)	C29—S1—C2	93.4 (1)
N1—C1—C2—C13	−95.25 (13)	C15—C14—C21—C22	−69.70 (16)
C12—C1—C2—C13	29.09 (17)	C28—C21—C22—C23	−79.2 (2)
C6—C1—C2—C13	144.34 (12)	C14—C21—C22—C23	100.66 (17)
N1—C1—C2—C3	21.50 (14)	C21—C22—C23—C24	71.3 (2)
C12—C1—C2—C3	145.83 (13)	C22—C23—C24—C25	−70.2 (3)
C6—C1—C2—C3	−98.92 (13)	C23—C24—C25—C26	100.0 (2)
N1—C1—C2—S1	148.60 (10)	C24—C25—C26—C27	−50.4 (3)
C12—C1—C2—S1	−87.06 (14)	C25—C26—C27—C28	−55.4 (2)
C6—C1—C2—S1	28.19 (14)	C14—C21—C28—N4	0.7 (2)
C13—C2—C3—C30	−109.68 (14)	C22—C21—C28—N4	−179.49 (14)
C1—C2—C3—C30	132.30 (13)	C14—C21—C28—C27	−177.84 (14)
S1—C2—C3—C30	8.40 (17)	C22—C21—C28—C27	2.0 (2)
C13—C2—C3—C4	121.68 (13)	C26—C27—C28—C21	92.4 (2)
C1—C2—C3—C4	3.66 (14)	C26—C27—C28—N4	−86.26 (17)
S1—C2—C3—C4	−120.24 (12)	C4—C3—C30—C31	−119.10 (17)
C30—C3—C4—N1	−159.29 (12)	C2—C3—C30—C31	117.03 (16)
C2—C3—C4—N1	−27.77 (15)	C4—C3—C30—C35	56.0 (2)
N1—C1—C6—O1	−55.4 (2)	C2—C3—C30—C35	−67.8 (2)
C12—C1—C6—O1	−176.38 (15)	C35—C30—C31—C32	−1.0 (2)
C2—C1—C6—O1	57.59 (19)	C3—C30—C31—C32	174.36 (15)
N1—C1—C6—N2	123.37 (13)	C30—C31—C32—C33	−0.1 (3)
C12—C1—C6—N2	2.35 (15)	C31—C32—C33—C34	1.2 (3)
C2—C1—C6—N2	−123.67 (13)	C31—C32—C33—C36	−176.24 (18)
C12—C7—C8—C9	−1.2 (2)	C32—C33—C34—C35	−1.3 (3)
N2—C7—C8—C9	173.80 (16)	C36—C33—C34—C35	176.18 (17)
C7—C8—C9—C10	−0.5 (3)	C33—C34—C35—C30	0.2 (3)
C8—C9—C10—C11	0.9 (3)	C31—C30—C35—C34	0.9 (2)
C9—C10—C11—C12	0.5 (3)	C3—C30—C35—C34	−174.30 (15)
C10—C11—C12—C7	−2.2 (2)	C3—C4—N1—C5	173.74 (14)
C10—C11—C12—C1	−174.26 (15)	C3—C4—N1—C1	44.53 (15)
C8—C7—C12—C11	2.6 (2)	C12—C1—N1—C4	−169.52 (12)
N2—C7—C12—C11	−173.23 (14)	C6—C1—N1—C4	75.96 (15)
C8—C7—C12—C1	176.32 (14)	C2—C1—N1—C4	−41.13 (14)
N2—C7—C12—C1	0.49 (17)	C12—C1—N1—C5	61.60 (18)
N1—C1—C12—C11	49.3 (2)	C6—C1—N1—C5	−52.92 (18)
C6—C1—C12—C11	171.06 (16)	C2—C1—N1—C5	−170.02 (14)
C2—C1—C12—C11	−69.7 (2)	O1—C6—N2—C7	176.47 (15)
N1—C1—C12—C7	−123.43 (14)	C1—C6—N2—C7	−2.26 (17)
C6—C1—C12—C7	−1.67 (15)	C8—C7—N2—C6	−174.33 (16)
C2—C1—C12—C7	117.58 (14)	C12—C7—N2—C6	1.18 (18)
C3—C2—C13—O2	−46.80 (19)	O2—C13—N3—C29	176.03 (13)
C1—C2—C13—O2	67.12 (18)	C2—C13—N3—C29	−3.17 (18)
S1—C2—C13—O2	−172.35 (13)	O2—C13—N3—C14	4.4 (2)
C3—C2—C13—N3	132.39 (13)	C2—C13—N3—C14	−174.76 (12)
C1—C2—C13—N3	−113.69 (13)	N4—C29—N3—C13	177.30 (13)
S1—C2—C13—N3	6.84 (14)	S1—C29—N3—C13	−2.50 (16)
N3—C14—C15—C16	−119.92 (15)	N4—C29—N3—C14	−11.2 (2)
C21—C14—C15—C16	117.82 (16)	S1—C29—N3—C14	169.03 (10)
N3—C14—C15—C20	62.90 (18)	C21—C14—N3—C13	−170.81 (12)
C21—C14—C15—C20	−59.36 (19)	C15—C14—N3—C13	65.26 (17)
C20—C15—C16—C17	2.1 (3)	C21—C14—N3—C29	17.96 (18)
C14—C15—C16—C17	−175.17 (16)	C15—C14—N3—C29	−105.97 (15)
C15—C16—C17—C18	−0.2 (3)	N3—C29—N4—C28	−3.1 (2)
C16—C17—C18—C19	−1.8 (3)	S1—C29—N4—C28	176.70 (10)
C17—C18—C19—C20	2.0 (3)	C21—C28—N4—C29	8.4 (2)
C16—C15—C20—C19	−1.9 (3)	C27—C28—N4—C29	−172.98 (13)
C14—C15—C20—C19	175.37 (17)	N4—C29—S1—C2	−174.08 (13)
C18—C19—C20—C15	−0.1 (3)	N3—C29—S1—C2	5.72 (11)
N3—C14—C21—C28	−12.96 (19)	C13—C2—S1—C29	−6.88 (10)
C15—C14—C21—C28	110.13 (16)	C3—C2—S1—C29	−127.18 (11)
N3—C14—C21—C22	167.21 (12)	C1—C2—S1—C29	112.86 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N4^i	0.86	2.13	2.975 (2)	170
C3—H3···O2	0.98	2.43	2.932 (2)	111
C4—H4A···O1	0.97	2.50	3.069 (2)	117
C11—H11···O2	0.93	2.49	3.097 (2)	123
C35—H35···O1	0.93	2.58	3.426 (3)	152

Symmetry code: (i) −x+2, −y+1, −z+1.