2-(Dibutyl-amino)-3-(4-fluoro-phen-yl)-5,6,7,8-tetra-hydro-7-methyl-6,8-di-phenyl-pyridine-[3',4':2,3]thieno[5,4-d]pyrimidin-4(3H)-one.

In the crystal structure of the title compound, C(36)H(39)FN(4)OS, the two fused rings of the thienopyrimidine system are coplanar. The 4-fluoro-phenyl ring is twisted with respect to the heterocyclic pyrimidinone ring by 67.21 (14)°. The piperidine ring shows a half-chair conformation. One of the n-butyl chains is disordered equally over two sites. The crystal packing is stabilized by C-H⋯O hydrogen bonds.

Related literature

The preparation and biological activity are described by Walter (1999a ▶,b ▶). For related literature, see: Ding et al. (2004 ▶). For the crystal structures of other fused pyrimidinone derivatives, see: Hu et al. (2006 ▶, 2007 ▶).

Experimental

Crystal data

C36H39FN4OS

M = 594.77

Monoclinic,

a = 13.723 (4) Å

b = 9.836 (3) Å

c = 24.5496 (15) Å

β = 101.342 (2)°

V = 3249.0 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 294 (2) K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.973, T max = 0.986

32225 measured reflections

6359 independent reflections

4457 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.178

S = 1.10

6359 reflections

420 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002845/bt2671sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002845/bt2671Isup2.hkl

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

C36H39FN4OS	F000 = 1264
Mr = 594.77	Dx = 1.216 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4792 reflections
a = 13.723 (4) Å	θ = 2.2–21.1º
b = 9.836 (3) Å	µ = 0.14 mm−1
c = 24.5496 (15) Å	T = 294 (2) K
β = 101.342 (2)º	Block, colorless
V = 3249.0 (14) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Bruker SMART 4K CCD area-detector diffractometer	6359 independent reflections
Radiation source: fine-focus sealed tube	4457 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.049
T = 294(2) K	θmax = 26.0º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −16→16
Tmin = 0.973, Tmax = 0.986	k = −12→12
32225 measured reflections	l = −29→30

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)] = 0.075	H-atom parameters constrained
wR(F2) = 0.178	w = 1/[σ2(Fo2) + (0.0743P)2 + 1.2986P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
6359 reflections	Δρmax = 0.40 e Å−3
420 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.3447 (2)	0.2687 (3)	0.22128 (13)	0.0579 (8)
C2	0.3770 (3)	0.3694 (5)	0.19044 (17)	0.0870 (12)
H2	0.3466	0.4543	0.1877	0.104*
C3	0.4545 (4)	0.3456 (7)	0.1635 (2)	0.1172 (18)
H3	0.4759	0.4152	0.1431	0.141*
C4	0.4996 (4)	0.2237 (9)	0.1661 (3)	0.136 (3)
H4	0.5511	0.2084	0.1472	0.163*
C5	0.4692 (4)	0.1243 (7)	0.1963 (3)	0.131 (2)
H5	0.5001	0.0399	0.1982	0.158*
C6	0.3933 (3)	0.1448 (4)	0.22453 (19)	0.0905 (13)
H6	0.3745	0.0750	0.2459	0.109*
C7	0.2588 (2)	0.2901 (3)	0.25038 (12)	0.0510 (7)
H7	0.2445	0.2034	0.2668	0.061*
C8	0.2858 (2)	0.3941 (3)	0.29718 (11)	0.0510 (7)
H8A	0.3355	0.3555	0.3267	0.061*
H8B	0.3143	0.4739	0.2832	0.061*
C9	0.19730 (18)	0.4348 (3)	0.31993 (10)	0.0411 (6)
C10	0.10476 (18)	0.4041 (3)	0.29181 (11)	0.0427 (6)
C11	0.1498 (2)	0.2452 (4)	0.16164 (14)	0.0767 (11)
H11A	0.1524	0.1519	0.1733	0.115*
H11B	0.1998	0.2612	0.1400	0.115*
H11C	0.0854	0.2645	0.1396	0.115*
C12	0.08097 (19)	0.3292 (3)	0.23755 (11)	0.0474 (7)
H12	0.0669	0.2341	0.2450	0.057*
C13	−0.0112 (2)	0.3913 (3)	0.20114 (11)	0.0503 (7)
C14	−0.1018 (2)	0.3286 (4)	0.19700 (14)	0.0644 (9)
H14	−0.1059	0.2453	0.2143	0.077*
C15	−0.1881 (3)	0.3895 (5)	0.16690 (18)	0.0912 (13)
H15	−0.2494	0.3472	0.1643	0.109*
C16	−0.1813 (3)	0.5119 (5)	0.14142 (17)	0.0936 (14)
H16	−0.2383	0.5533	0.1217	0.112*
C17	−0.0902 (3)	0.5741 (4)	0.14485 (14)	0.0851 (12)
H17	−0.0860	0.6567	0.1270	0.102*
C18	−0.0060 (3)	0.5145 (4)	0.17451 (13)	0.0715 (10)
H18	0.0552	0.5571	0.1768	0.086*
C19	0.19517 (18)	0.5079 (3)	0.37045 (10)	0.0398 (6)
C20	0.10039 (18)	0.5317 (3)	0.37838 (10)	0.0421 (6)
C21	0.27613 (19)	0.5607 (3)	0.41048 (11)	0.0416 (6)
C22	0.14679 (18)	0.6441 (3)	0.45949 (11)	0.0438 (7)
C23	0.32616 (19)	0.6976 (3)	0.49318 (11)	0.0434 (6)
C24	0.3317 (2)	0.8363 (3)	0.49281 (12)	0.0539 (8)
H24	0.2826	0.8865	0.4699	0.065*
C25	0.4101 (2)	0.9018 (4)	0.52640 (15)	0.0714 (10)
H25	0.4140	0.9962	0.5271	0.086*
C26	0.4817 (2)	0.8244 (4)	0.55861 (15)	0.0740 (10)
C27	0.4788 (2)	0.6871 (4)	0.55940 (14)	0.0716 (10)
H27	0.5289	0.6376	0.5819	0.086*
C28	0.3998 (2)	0.6217 (3)	0.52609 (12)	0.0581 (8)
H28	0.3962	0.5273	0.5258	0.070*
C29	0.0333 (2)	0.7957 (3)	0.49500 (14)	0.0594 (8)
H29A	0.0426	0.8720	0.5205	0.071*
H29B	0.0223	0.8328	0.4577	0.071*
C30	−0.0583 (2)	0.7227 (4)	0.50169 (15)	0.0665 (9)
H30A	−0.0484	0.6841	0.5387	0.080*
H30B	−0.0704	0.6484	0.4752	0.080*
C31	−0.1489 (2)	0.8153 (4)	0.49285 (15)	0.0700 (10)
H31A	−0.1369	0.8882	0.5199	0.084*
H31B	−0.1571	0.8559	0.4562	0.084*
C32	−0.2429 (3)	0.7447 (5)	0.4977 (2)	0.1140 (17)
H32A	−0.2572	0.6750	0.4699	0.171*
H32B	−0.2965	0.8092	0.4925	0.171*
H32C	−0.2357	0.7043	0.5339	0.171*
C33	0.1645 (2)	0.6617 (4)	0.56025 (12)	0.0669 (9)
H33A	0.1087	0.6153	0.5709	0.080*	0.540 (12)
H33B	0.2126	0.5920	0.5563	0.080*	0.540 (12)
H33C	0.2243	0.6084	0.5614	0.080*	0.460 (12)
H33D	0.1146	0.6048	0.5719	0.080*	0.460 (12)
C34	0.2095 (12)	0.7431 (12)	0.6075 (4)	0.066 (3)	0.540 (12)
H34A	0.1596	0.8048	0.6163	0.079*	0.540 (12)
H34B	0.2616	0.7980	0.5971	0.079*	0.540 (12)
C35	0.2531 (8)	0.6640 (10)	0.6590 (3)	0.068 (3)	0.540 (12)
H35A	0.2014	0.6101	0.6704	0.082*	0.540 (12)
H35B	0.3035	0.6023	0.6509	0.082*	0.540 (12)
C36	0.2984 (9)	0.7568 (10)	0.7053 (4)	0.104 (4)	0.540 (12)
H36A	0.3532	0.8046	0.6952	0.156*	0.540 (12)
H36B	0.3216	0.7044	0.7383	0.156*	0.540 (12)
H36C	0.2494	0.8210	0.7121	0.156*	0.540 (12)
C35'	0.2274 (7)	0.7482 (16)	0.6599 (3)	0.084 (4)	0.460 (12)
H35C	0.2191	0.8236	0.6840	0.101*	0.460 (12)
H35D	0.1883	0.6727	0.6692	0.101*	0.460 (12)
C36'	0.3346 (8)	0.7077 (14)	0.6708 (7)	0.118 (5)	0.460 (12)
H36D	0.3423	0.6263	0.6505	0.177*	0.460 (12)
H36E	0.3570	0.6914	0.7098	0.177*	0.460 (12)
H36F	0.3733	0.7794	0.6591	0.177*	0.460 (12)
C34'	0.1879 (13)	0.7894 (15)	0.6001 (5)	0.073 (4)	0.460 (12)
H34C	0.2365	0.8465	0.5873	0.088*	0.460 (12)
H34D	0.1277	0.8424	0.5982	0.088*	0.460 (12)
F1	0.56013 (15)	0.8889 (3)	0.59104 (11)	0.1141 (9)
N1	0.16778 (16)	0.3340 (3)	0.21066 (9)	0.0490 (6)
N2	0.07372 (15)	0.5982 (2)	0.42205 (9)	0.0460 (6)
N3	0.24634 (15)	0.6284 (2)	0.45583 (9)	0.0425 (5)
N4	0.12771 (17)	0.7164 (3)	0.50414 (9)	0.0543 (6)
O1	0.36369 (14)	0.5545 (2)	0.40787 (8)	0.0573 (6)
S1	0.01216 (5)	0.46324 (8)	0.32512 (3)	0.0508 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0445 (16)	0.074 (2)	0.0542 (19)	0.0018 (15)	0.0070 (14)	−0.0218 (17)
C2	0.079 (3)	0.107 (3)	0.085 (3)	−0.001 (2)	0.041 (2)	0.002 (2)
C3	0.087 (3)	0.182 (6)	0.097 (3)	−0.014 (4)	0.054 (3)	−0.018 (4)
C4	0.056 (3)	0.235 (8)	0.125 (5)	−0.007 (4)	0.039 (3)	−0.087 (5)
C5	0.061 (3)	0.156 (6)	0.174 (6)	0.032 (3)	0.016 (3)	−0.081 (5)
C6	0.067 (2)	0.089 (3)	0.112 (3)	0.014 (2)	0.008 (2)	−0.025 (2)
C7	0.0510 (16)	0.0564 (18)	0.0459 (17)	0.0009 (14)	0.0106 (13)	−0.0015 (14)
C8	0.0448 (15)	0.068 (2)	0.0388 (15)	0.0030 (14)	0.0046 (12)	−0.0073 (14)
C9	0.0400 (14)	0.0488 (16)	0.0347 (14)	−0.0002 (12)	0.0081 (11)	0.0020 (12)
C10	0.0399 (14)	0.0525 (17)	0.0355 (14)	−0.0058 (12)	0.0066 (11)	−0.0016 (12)
C11	0.058 (2)	0.119 (3)	0.055 (2)	−0.014 (2)	0.0159 (16)	−0.035 (2)
C12	0.0450 (15)	0.0556 (18)	0.0411 (16)	−0.0080 (13)	0.0071 (12)	−0.0064 (13)
C13	0.0488 (16)	0.067 (2)	0.0336 (15)	−0.0044 (14)	0.0038 (12)	−0.0170 (14)
C14	0.0482 (18)	0.077 (2)	0.066 (2)	−0.0068 (16)	0.0060 (15)	−0.0212 (18)
C15	0.053 (2)	0.120 (4)	0.094 (3)	−0.001 (2)	−0.002 (2)	−0.039 (3)
C16	0.084 (3)	0.113 (4)	0.068 (3)	0.033 (3)	−0.023 (2)	−0.029 (3)
C17	0.102 (3)	0.091 (3)	0.051 (2)	0.012 (2)	−0.012 (2)	−0.0048 (19)
C18	0.080 (2)	0.080 (3)	0.0490 (19)	−0.0041 (19)	−0.0023 (17)	0.0017 (18)
C19	0.0375 (14)	0.0448 (15)	0.0364 (14)	−0.0001 (11)	0.0058 (11)	0.0009 (12)
C20	0.0377 (14)	0.0516 (17)	0.0358 (14)	0.0007 (12)	0.0042 (11)	0.0012 (12)
C21	0.0390 (15)	0.0494 (17)	0.0355 (14)	0.0040 (12)	0.0051 (11)	0.0017 (12)
C22	0.0379 (14)	0.0559 (17)	0.0366 (15)	0.0056 (12)	0.0051 (11)	−0.0015 (13)
C23	0.0402 (14)	0.0524 (18)	0.0357 (14)	0.0009 (12)	0.0029 (11)	−0.0049 (12)
C24	0.0487 (16)	0.059 (2)	0.0503 (17)	0.0029 (14)	0.0008 (13)	0.0050 (15)
C25	0.064 (2)	0.061 (2)	0.085 (3)	−0.0114 (17)	0.0048 (18)	−0.0115 (19)
C26	0.0468 (18)	0.093 (3)	0.075 (2)	−0.0105 (18)	−0.0055 (16)	−0.026 (2)
C27	0.0550 (19)	0.083 (3)	0.065 (2)	0.0176 (17)	−0.0177 (16)	−0.0154 (19)
C28	0.0512 (17)	0.0601 (19)	0.0563 (19)	0.0085 (15)	−0.0060 (14)	−0.0049 (15)
C29	0.0628 (19)	0.058 (2)	0.0566 (19)	0.0073 (16)	0.0109 (15)	−0.0101 (16)
C30	0.062 (2)	0.069 (2)	0.071 (2)	0.0080 (17)	0.0174 (17)	−0.0034 (18)
C31	0.061 (2)	0.080 (2)	0.068 (2)	0.0180 (18)	0.0116 (17)	0.0058 (19)
C32	0.068 (3)	0.108 (4)	0.170 (5)	0.010 (2)	0.032 (3)	0.019 (3)
C33	0.0541 (18)	0.104 (3)	0.0436 (18)	0.0043 (18)	0.0125 (14)	−0.0012 (18)
C34	0.075 (8)	0.078 (6)	0.038 (5)	0.001 (5)	−0.003 (4)	0.002 (4)
C35	0.071 (6)	0.074 (6)	0.057 (4)	−0.016 (4)	0.006 (4)	−0.001 (4)
C36	0.123 (8)	0.112 (8)	0.068 (6)	−0.016 (6)	−0.004 (5)	−0.002 (5)
C35'	0.084 (7)	0.113 (11)	0.053 (6)	−0.016 (7)	0.005 (5)	−0.010 (6)
C36'	0.113 (10)	0.119 (10)	0.115 (12)	0.018 (8)	0.005 (8)	0.003 (8)
C34'	0.060 (7)	0.113 (11)	0.042 (6)	0.007 (7)	−0.003 (4)	−0.001 (7)
F1	0.0640 (13)	0.128 (2)	0.132 (2)	−0.0187 (13)	−0.0241 (13)	−0.0511 (17)
N1	0.0426 (13)	0.0682 (16)	0.0365 (12)	−0.0072 (11)	0.0083 (10)	−0.0095 (11)
N2	0.0389 (12)	0.0603 (15)	0.0380 (13)	0.0010 (11)	0.0055 (10)	−0.0082 (11)
N3	0.0376 (12)	0.0517 (14)	0.0365 (12)	0.0029 (10)	0.0028 (9)	−0.0032 (10)
N4	0.0461 (13)	0.0767 (18)	0.0388 (13)	0.0114 (12)	0.0047 (10)	−0.0105 (12)
O1	0.0381 (11)	0.0840 (15)	0.0489 (12)	0.0018 (10)	0.0061 (8)	−0.0122 (11)
S1	0.0361 (4)	0.0717 (5)	0.0441 (4)	−0.0058 (3)	0.0064 (3)	−0.0110 (4)

C1—C2	1.373 (5)	C23—C28	1.382 (4)
C1—C6	1.385 (5)	C23—N3	1.452 (3)
C1—C7	1.509 (4)	C24—C25	1.380 (4)
C2—C3	1.378 (6)	C24—H24	0.9300
C2—H2	0.9300	C25—C26	1.366 (5)
C3—C4	1.345 (8)	C25—H25	0.9300
C3—H3	0.9300	C26—C27	1.352 (5)
C4—C5	1.343 (8)	C26—F1	1.363 (3)
C4—H4	0.9300	C27—C28	1.381 (4)
C5—C6	1.374 (7)	C27—H27	0.9300
C5—H5	0.9300	C28—H28	0.9300
C6—H6	0.9300	C29—C30	1.485 (4)
C7—N1	1.489 (3)	C29—N4	1.491 (4)
C7—C8	1.528 (4)	C29—H29A	0.9700
C7—H7	0.9800	C29—H29B	0.9700
C8—C9	1.488 (4)	C30—C31	1.521 (4)
C8—H8A	0.9700	C30—H30A	0.9700
C8—H8B	0.9700	C30—H30B	0.9700
C9—C10	1.355 (3)	C31—C32	1.491 (5)
C9—C19	1.439 (4)	C31—H31A	0.9700
C10—C12	1.501 (4)	C31—H31B	0.9700
C10—S1	1.741 (3)	C32—H32A	0.9600
C11—N1	1.468 (4)	C32—H32B	0.9600
C11—H11A	0.9600	C32—H32C	0.9600
C11—H11B	0.9600	C33—C34	1.444 (9)
C11—H11C	0.9600	C33—N4	1.473 (4)
C12—N1	1.472 (3)	C33—C34'	1.585 (12)
C12—C13	1.525 (4)	C33—H33A	0.9700
C12—H12	0.9800	C33—H33B	0.9700
C13—C14	1.374 (4)	C33—H33C	0.9700
C13—C18	1.385 (5)	C33—H33D	0.9700
C14—C15	1.401 (5)	C34—C35	1.506 (10)
C14—H14	0.9300	C34—H34A	0.9700
C15—C16	1.368 (6)	C34—H34B	0.9700
C15—H15	0.9300	C35—C36	1.494 (10)
C16—C17	1.379 (6)	C35—H35A	0.9700
C16—H16	0.9300	C35—H35B	0.9700
C17—C18	1.371 (5)	C36—H36A	0.9600
C17—H17	0.9300	C36—H36B	0.9600
C18—H18	0.9300	C36—H36C	0.9600
C19—C20	1.373 (3)	C35'—C36'	1.496 (12)
C19—C21	1.428 (3)	C35'—C34'	1.517 (11)
C20—N2	1.366 (3)	C35'—H35C	0.9700
C20—S1	1.734 (3)	C35'—H35D	0.9700
C21—O1	1.217 (3)	C36'—H36D	0.9600
C21—N3	1.424 (3)	C36'—H36E	0.9600
C22—N2	1.301 (3)	C36'—H36F	0.9600
C22—N4	1.375 (3)	C34'—H34C	0.9700
C22—N3	1.395 (3)	C34'—H34D	0.9700
C23—C24	1.366 (4)
C2—C1—C6	117.6 (4)	C27—C26—F1	118.6 (3)
C2—C1—C7	121.9 (3)	C27—C26—C25	123.0 (3)
C6—C1—C7	120.5 (3)	F1—C26—C25	118.3 (4)
C1—C2—C3	120.4 (5)	C26—C27—C28	118.6 (3)
C1—C2—H2	119.8	C26—C27—H27	120.7
C3—C2—H2	119.8	C28—C27—H27	120.7
C4—C3—C2	121.4 (6)	C27—C28—C23	119.6 (3)
C4—C3—H3	119.3	C27—C28—H28	120.2
C2—C3—H3	119.3	C23—C28—H28	120.2
C5—C4—C3	118.9 (5)	C30—C29—N4	117.4 (3)
C5—C4—H4	120.5	C30—C29—H29A	108.0
C3—C4—H4	120.5	N4—C29—H29A	108.0
C4—C5—C6	121.4 (6)	C30—C29—H29B	108.0
C4—C5—H5	119.3	N4—C29—H29B	108.0
C6—C5—H5	119.3	H29A—C29—H29B	107.2
C5—C6—C1	120.3 (5)	C29—C30—C31	112.4 (3)
C5—C6—H6	119.9	C29—C30—H30A	109.1
C1—C6—H6	119.9	C31—C30—H30A	109.1
N1—C7—C1	111.3 (2)	C29—C30—H30B	109.1
N1—C7—C8	110.3 (2)	C31—C30—H30B	109.1
C1—C7—C8	110.6 (2)	H30A—C30—H30B	107.9
N1—C7—H7	108.2	C32—C31—C30	113.9 (3)
C1—C7—H7	108.2	C32—C31—H31A	108.8
C8—C7—H7	108.2	C30—C31—H31A	108.8
C9—C8—C7	111.5 (2)	C32—C31—H31B	108.8
C9—C8—H8A	109.3	C30—C31—H31B	108.8
C7—C8—H8A	109.3	H31A—C31—H31B	107.7
C9—C8—H8B	109.3	C31—C32—H32A	109.5
C7—C8—H8B	109.3	C31—C32—H32B	109.5
H8A—C8—H8B	108.0	H32A—C32—H32B	109.5
C10—C9—C19	112.0 (2)	C31—C32—H32C	109.5
C10—C9—C8	120.1 (2)	H32A—C32—H32C	109.5
C19—C9—C8	127.9 (2)	H32B—C32—H32C	109.5
C9—C10—C12	125.4 (2)	C34—C33—N4	124.2 (6)
C9—C10—S1	112.6 (2)	N4—C33—C34'	106.1 (6)
C12—C10—S1	121.97 (19)	C34—C33—H33A	106.3
N1—C11—H11A	109.5	N4—C33—H33A	106.3
N1—C11—H11B	109.5	C34—C33—H33B	106.3
H11A—C11—H11B	109.5	N4—C33—H33B	106.3
N1—C11—H11C	109.5	H33A—C33—H33B	106.4
H11A—C11—H11C	109.5	N4—C33—H33C	110.9
H11B—C11—H11C	109.5	C34'—C33—H33C	110.1
N1—C12—C10	109.2 (2)	N4—C33—H33D	110.8
N1—C12—C13	112.0 (2)	C34'—C33—H33D	110.2
C10—C12—C13	109.5 (2)	H33C—C33—H33D	108.8
N1—C12—H12	108.7	C33—C34—C35	115.1 (8)
C10—C12—H12	108.7	C33—C34—H34A	108.5
C13—C12—H12	108.7	C35—C34—H34A	108.5
C14—C13—C18	119.1 (3)	C33—C34—H34B	108.5
C14—C13—C12	119.9 (3)	C35—C34—H34B	108.5
C18—C13—C12	120.9 (3)	H34A—C34—H34B	107.5
C13—C14—C15	120.4 (4)	C36—C35—C34	111.1 (7)
C13—C14—H14	119.8	C36—C35—H35A	109.4
C15—C14—H14	119.8	C34—C35—H35A	109.4
C16—C15—C14	119.3 (4)	C36—C35—H35B	109.4
C16—C15—H15	120.3	C34—C35—H35B	109.4
C14—C15—H15	120.3	H35A—C35—H35B	108.0
C15—C16—C17	120.4 (4)	C36'—C35'—C34'	113.4 (10)
C15—C16—H16	119.8	C36'—C35'—H35C	108.9
C17—C16—H16	119.8	C34'—C35'—H35C	108.9
C18—C17—C16	120.1 (4)	C36'—C35'—H35D	108.9
C18—C17—H17	120.0	C34'—C35'—H35D	108.9
C16—C17—H17	120.0	H35C—C35'—H35D	107.7
C17—C18—C13	120.6 (4)	C35'—C36'—H36D	109.5
C17—C18—H18	119.7	C35'—C36'—H36E	109.5
C13—C18—H18	119.7	H36D—C36'—H36E	109.5
C20—C19—C21	118.1 (2)	C35'—C36'—H36F	109.5
C20—C19—C9	112.8 (2)	H36D—C36'—H36F	109.5
C21—C19—C9	129.0 (2)	H36E—C36'—H36F	109.5
N2—C20—C19	126.9 (2)	C35'—C34'—C33	112.1 (9)
N2—C20—S1	121.52 (19)	C35'—C34'—H34C	109.2
C19—C20—S1	111.6 (2)	C33—C34'—H34C	109.2
O1—C21—N3	120.2 (2)	C35'—C34'—H34D	109.2
O1—C21—C19	126.0 (2)	C33—C34'—H34D	109.2
N3—C21—C19	113.8 (2)	H34C—C34'—H34D	107.9
N2—C22—N4	120.1 (2)	C11—N1—C12	109.2 (2)
N2—C22—N3	123.0 (2)	C11—N1—C7	110.4 (2)
N4—C22—N3	116.8 (2)	C12—N1—C7	110.2 (2)
C24—C23—C28	120.5 (3)	C22—N2—C20	115.6 (2)
C24—C23—N3	120.0 (2)	C22—N3—C21	122.5 (2)
C28—C23—N3	119.4 (3)	C22—N3—C23	122.3 (2)
C23—C24—C25	120.0 (3)	C21—N3—C23	114.6 (2)
C23—C24—H24	120.0	C22—N4—C33	118.2 (2)
C25—C24—H24	120.0	C22—N4—C29	116.5 (2)
C26—C25—C24	118.3 (3)	C33—N4—C29	117.4 (2)
C26—C25—H25	120.9	C20—S1—C10	91.03 (12)
C24—C25—H25	120.9
C6—C1—C2—C3	0.7 (6)	C24—C25—C26—F1	178.8 (3)
C7—C1—C2—C3	−178.7 (4)	F1—C26—C27—C28	−179.4 (3)
C1—C2—C3—C4	0.7 (7)	C25—C26—C27—C28	0.1 (6)
C2—C3—C4—C5	−1.0 (9)	C26—C27—C28—C23	−0.2 (5)
C3—C4—C5—C6	0.0 (9)	C24—C23—C28—C27	0.9 (5)
C4—C5—C6—C1	1.5 (8)	N3—C23—C28—C27	176.4 (3)
C2—C1—C6—C5	−1.8 (5)	N4—C29—C30—C31	178.4 (3)
C7—C1—C6—C5	177.7 (4)	C29—C30—C31—C32	178.4 (4)
C2—C1—C7—N1	56.1 (4)	N4—C33—C34—C35	−172.7 (8)
C6—C1—C7—N1	−123.3 (3)	C34'—C33—C34—C35	157 (5)
C2—C1—C7—C8	−66.9 (4)	C33—C34—C35—C36	179.6 (12)
C6—C1—C7—C8	113.7 (3)	C36'—C35'—C34'—C33	78.0 (18)
N1—C7—C8—C9	46.5 (3)	C34—C33—C34'—C35'	−25 (3)
C1—C7—C8—C9	170.1 (3)	N4—C33—C34'—C35'	−179.7 (10)
C7—C8—C9—C10	−14.1 (4)	C10—C12—N1—C11	172.2 (3)
C7—C8—C9—C19	166.6 (3)	C13—C12—N1—C11	−66.3 (3)
C19—C9—C10—C12	179.6 (2)	C10—C12—N1—C7	50.8 (3)
C8—C9—C10—C12	0.3 (4)	C13—C12—N1—C7	172.3 (2)
C19—C9—C10—S1	0.3 (3)	C1—C7—N1—C11	48.7 (3)
C8—C9—C10—S1	−179.0 (2)	C8—C7—N1—C11	171.9 (3)
C9—C10—C12—N1	−18.6 (4)	C1—C7—N1—C12	169.4 (2)
S1—C10—C12—N1	160.7 (2)	C8—C7—N1—C12	−67.5 (3)
C9—C10—C12—C13	−141.6 (3)	N4—C22—N2—C20	177.8 (2)
S1—C10—C12—C13	37.6 (3)	N3—C22—N2—C20	0.5 (4)
N1—C12—C13—C14	137.7 (3)	C19—C20—N2—C22	0.6 (4)
C10—C12—C13—C14	−100.9 (3)	S1—C20—N2—C22	179.5 (2)
N1—C12—C13—C18	−45.9 (4)	N2—C22—N3—C21	0.1 (4)
C10—C12—C13—C18	75.4 (3)	N4—C22—N3—C21	−177.3 (2)
C18—C13—C14—C15	−1.0 (5)	N2—C22—N3—C23	170.3 (3)
C12—C13—C14—C15	175.4 (3)	N4—C22—N3—C23	−7.1 (4)
C13—C14—C15—C16	0.3 (5)	O1—C21—N3—C22	176.8 (3)
C14—C15—C16—C17	0.6 (6)	C19—C21—N3—C22	−1.6 (4)
C15—C16—C17—C18	−0.9 (6)	O1—C21—N3—C23	5.9 (4)
C16—C17—C18—C13	0.2 (5)	C19—C21—N3—C23	−172.5 (2)
C14—C13—C18—C17	0.7 (5)	C24—C23—N3—C22	−64.1 (4)
C12—C13—C18—C17	−175.6 (3)	C28—C23—N3—C22	120.4 (3)
C10—C9—C19—C20	−0.8 (3)	C24—C23—N3—C21	106.9 (3)
C8—C9—C19—C20	178.5 (3)	C28—C23—N3—C21	−68.6 (3)
C10—C9—C19—C21	−178.4 (3)	N2—C22—N4—C33	119.2 (3)
C8—C9—C19—C21	0.9 (5)	N3—C22—N4—C33	−63.3 (4)
C21—C19—C20—N2	−2.2 (4)	N2—C22—N4—C29	−29.2 (4)
C9—C19—C20—N2	180.0 (3)	N3—C22—N4—C29	148.3 (3)
C21—C19—C20—S1	178.8 (2)	C34—C33—N4—C22	138.2 (9)
C9—C19—C20—S1	1.0 (3)	C34'—C33—N4—C22	148.7 (8)
C20—C19—C21—O1	−175.9 (3)	C34—C33—N4—C29	−73.7 (9)
C9—C19—C21—O1	1.5 (5)	C34'—C33—N4—C29	−63.2 (8)
C20—C19—C21—N3	2.5 (4)	C30—C29—N4—C22	85.0 (4)
C9—C19—C21—N3	179.9 (2)	C30—C29—N4—C33	−63.7 (4)
C28—C23—C24—C25	−1.5 (5)	N2—C20—S1—C10	−179.7 (2)
N3—C23—C24—C25	−177.0 (3)	C19—C20—S1—C10	−0.7 (2)
C23—C24—C25—C26	1.3 (5)	C9—C10—S1—C20	0.2 (2)
C24—C25—C26—C27	−0.6 (6)	C12—C10—S1—C20	−179.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1i	0.93	2.47	3.304 (6)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.93	2.47	3.304 (6)	149

Symmetry code: (i) .