7′′-Benz­yl-9′′-benzyl­idene-4′-[4-(dimethyl­amino)phen­yl]-1′-meth­yl-5′′-phen­yl- 2′′,3′′,6′′,7′′,8′′,9′′-hexa­hydro-1H-indole-3(2H)-spiro-2′-pyrrolidine-3′-spiro-2′′-pyrido[4,3-d]thia­zolo[3,2-a]pyrimidine-2,2′′-dione acetonitrile disolvate

Hu, X.-F.; Feng, Y.-Q.; Su, Q.; Qiao, K.-J.

doi:10.1107/S1600536805015485

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7′′-Benzyl-9′′-benzylidene-4′-[4-(dimethylamino)phenyl]-1′-methyl-5′′-phenyl- 2′′,3′′,6′′,7′′,8′′,9′′-hexahydro-1H-indole-3(2H)-spiro-2′-pyrrolidine-3′-spiro-2′′-pyrido[4,3-d]thiazolo[3,2-a]pyrimidine-2,2′′-dione acetonitrile disolvate

X.-F. Hu, Y.-Q. Feng, Q. Su and K.-J. Qiao

The title compound, C₄₈H₄₄N₆O₂S·2C₂H₃N, was synthesized by the intermolecular [3+2]-cycloaddition of an azomethine ylide, derived from isatin and sarcosine by a decarboxylative route, and 7-benzyl-9-benzylidene-2-[4-(dimethylamino)benzylidene]-5-phenyl-2,3,6,7,8,9-hexahydro-5H-pyrido[4,3-d]thiazolo[3,2-a]pyrimidin-3-one. In the molecule, the two spiro junctions link a planar 2-oxindole system, a pyrrolidine ring in an envelope conformation and a thiazolidone ring of the fused pyrimidine ring system. The packing of the molecules in the crystal structure is mainly stabilized by N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805015485/sj6088sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805015485/sj6088Isup2.hkl Contains datablock I

CCDC reference: 274639

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.053
wR factor = 0.157
Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.92 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.80 Ratio

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent .........          3
PLAT220_ALERT_2_C Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       3.18 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C4'
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C6'
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C25
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C2'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C21
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C42
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C2
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C51
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C49
PLAT301_ALERT_3_C Main Residue  Disorder .........................      21.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      33.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      16.00 Deg.
              C2'  -C1   -C2      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       0.00 Deg.
              H1A  -C1   -H1C     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       0.00 Deg.
              H1B  -C1   -H1D     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       5.10 Deg.
              C41' -C40  -C41     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       2.60 Deg.
              H40A -C40  -H40B    1.555   1.555   1.555

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

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

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

7"-Benzyl-9"-benzylidene-4'-[4-(dimethylamino)phenyl]-1'-methyl-5"-phenyl- 2",3",6",7",8",9"-hexahydro-1H-indole-3(2H)-spiro-2'-pyrrolidine-3'-spiro-2''- pyrido[4,3-d]thiazolo[3,2-a]pyrimidine-2,2''-dione acetonitrile disolvate top

Crystal data top

C₄₈H₄₄N₆O₂S·2C₂H₃N	F(000) = 900
M_r = 851.06	D_x = 1.218 Mg m⁻³
Triclinic, P1	Melting point: 201 K
a = 12.4130 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.1265 (15) Å	Cell parameters from 3369 reflections
c = 15.1590 (18) Å	θ = 2.3–24.0°
α = 87.559 (2)°	µ = 0.12 mm⁻¹
β = 74.392 (2)°	T = 294 K
γ = 77.313 (2)°	Block, colorless
V = 2320.5 (5) Å³	0.26 × 0.22 × 0.20 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	8127 independent reflections
Radiation source: fine-focus sealed tube	5109 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker,1997)	h = −14→13
T_min = 0.960, T_max = 0.972	k = −13→15
11894 measured reflections	l = −18→17

Refinement top

Refinement on F²	66 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.053	w = 1/[σ²(F_o²) + (0.0629P)² + 1.1607P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.157	(Δ/σ)_max = 0.003
S = 1.03	Δρ_max = 0.43 e Å⁻³
8127 reflections	Δρ_min = −0.32 e Å⁻³
642 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.38776 (6)	0.82850 (6)	0.23151 (5)	0.0438 (2)
O1	0.13443 (17)	0.71519 (16)	0.20890 (13)	0.0500 (5)
O2	0.50109 (18)	0.86219 (16)	0.03387 (15)	0.0547 (6)
N1	−0.0030 (2)	0.86532 (18)	0.63964 (15)	0.0424 (6)
N2	0.28405 (19)	0.85995 (18)	0.40903 (15)	0.0409 (6)
N3	0.19263 (18)	0.78586 (17)	0.31729 (14)	0.0362 (5)
N4	0.3478 (2)	0.9972 (2)	0.03568 (18)	0.0487 (7)
H4	0.384 (3)	1.044 (3)	0.020 (2)	0.061 (10)*
N5	0.3155 (2)	0.75362 (19)	0.00839 (15)	0.0465 (6)
C1	−0.1177 (3)	0.9007 (2)	0.7011 (2)	0.0528 (8)
H1A	−0.1666	0.9430	0.6680	0.063*	0.48 (3)
H1B	−0.1135	0.9424	0.7500	0.063*	0.48 (3)
H1C	−0.1666	0.9430	0.6680	0.063*	0.52 (3)
H1D	−0.1135	0.9424	0.7500	0.063*	0.52 (3)
C2	−0.1689 (8)	0.8046 (6)	0.7413 (3)	0.046 (3)	0.48 (3)
C3	−0.1092 (14)	0.7232 (6)	0.7828 (3)	0.070 (3)	0.48 (3)
H3A	−0.0334	0.7210	0.7816	0.084*	0.48 (3)
C4	−0.163 (2)	0.6450 (8)	0.8260 (3)	0.103 (5)	0.48 (3)
H4A	−0.1227	0.5905	0.8538	0.124*	0.48 (3)
C5	−0.2759 (19)	0.6482 (11)	0.8278 (6)	0.099 (6)	0.48 (3)
H5A	−0.3117	0.5959	0.8567	0.119*	0.48 (3)
C6	−0.3356 (12)	0.7296 (12)	0.7863 (10)	0.106 (7)	0.48 (3)
H6A	−0.4114	0.7318	0.7875	0.127*	0.48 (3)
C7	−0.2821 (7)	0.8078 (9)	0.7430 (9)	0.084 (4)	0.48 (3)
H7A	−0.3221	0.8622	0.7153	0.101*	0.48 (3)
C2'	−0.1918 (6)	0.8253 (6)	0.7282 (5)	0.049 (3)	0.52 (3)
C3'	−0.1547 (13)	0.7442 (6)	0.7823 (2)	0.066 (3)	0.52 (3)
H3'A	−0.0834	0.7365	0.7937	0.079*	0.52 (3)
C4'	−0.2241 (18)	0.6746 (9)	0.8192 (4)	0.102 (6)	0.52 (3)
H4'A	−0.1992	0.6203	0.8554	0.122*	0.52 (3)
C5'	−0.3306 (15)	0.6861 (12)	0.8021 (9)	0.100 (7)	0.52 (3)
H5'A	−0.3770	0.6396	0.8268	0.120*	0.52 (3)
C6'	−0.3677 (8)	0.7673 (12)	0.7480 (13)	0.119 (6)	0.52 (3)
H6'A	−0.4390	0.7750	0.7365	0.143*	0.52 (3)
C7'	−0.2984 (4)	0.8369 (9)	0.7110 (10)	0.089 (4)	0.52 (3)
H7'A	−0.3232	0.8911	0.6748	0.106*	0.52 (3)
C8	0.0569 (2)	0.9513 (2)	0.62858 (19)	0.0457 (7)
H8A	0.0630	0.9699	0.6880	0.055*
H8B	0.0116	1.0116	0.6063	0.055*
C9	0.1744 (2)	0.9263 (2)	0.56401 (19)	0.0412 (7)
C10	0.2659 (3)	0.9553 (2)	0.5769 (2)	0.0511 (8)
H10	0.3339	0.9353	0.5312	0.061*
C11	0.2718 (3)	1.0151 (3)	0.6551 (2)	0.0560 (9)
C12	0.3648 (4)	0.9837 (3)	0.6919 (3)	0.0810 (12)
H12	0.4218	0.9259	0.6668	0.097*
C13	0.3736 (5)	1.0375 (4)	0.7657 (3)	0.1026 (16)
H13	0.4355	1.0142	0.7904	0.123*
C14	0.2935 (6)	1.1234 (5)	0.8022 (3)	0.1029 (18)
H14	0.3008	1.1598	0.8509	0.123*
C15	0.2015 (4)	1.1563 (4)	0.7666 (3)	0.0948 (16)
H15	0.1456	1.2149	0.7916	0.114*
C16	0.1911 (3)	1.1026 (3)	0.6934 (3)	0.0720 (11)
H16	0.1284	1.1261	0.6698	0.086*
C17	0.1830 (2)	0.8650 (2)	0.48234 (18)	0.0387 (7)
C18	0.0972 (2)	0.8204 (2)	0.47770 (18)	0.0375 (6)
C19	−0.0113 (2)	0.8299 (2)	0.55252 (18)	0.0436 (7)
H19A	−0.0721	0.8786	0.5341	0.052*
H19B	−0.0322	0.7624	0.5607	0.052*
C20	0.1052 (2)	0.7558 (2)	0.39540 (17)	0.0377 (6)
H20	0.0311	0.7730	0.3808	0.045*
C21	0.1350 (3)	0.6392 (2)	0.41054 (19)	0.0448 (7)
C22	0.2232 (3)	0.5971 (3)	0.4473 (3)	0.0768 (11)
H22	0.2635	0.6403	0.4658	0.092*
C23	0.2532 (4)	0.4899 (4)	0.4574 (4)	0.1048 (16)
H23	0.3150	0.4618	0.4810	0.126*
C24	0.1938 (6)	0.4257 (3)	0.4332 (4)	0.1053 (18)
H24	0.2130	0.3541	0.4416	0.126*
C25	0.1067 (6)	0.4673 (4)	0.3969 (3)	0.1092 (18)
H25	0.0662	0.4236	0.3795	0.131*
C26	0.0761 (4)	0.5738 (3)	0.3849 (3)	0.0766 (11)
H26	0.0156	0.6010	0.3595	0.092*
C27	0.2807 (2)	0.8256 (2)	0.33255 (18)	0.0367 (6)
C28	0.2046 (2)	0.7543 (2)	0.22955 (18)	0.0381 (6)
C29	0.3177 (2)	0.7670 (2)	0.16336 (18)	0.0383 (6)
C30	0.3019 (2)	0.8337 (2)	0.07756 (18)	0.0395 (7)
C31	0.1953 (2)	0.9195 (2)	0.08594 (18)	0.0402 (7)
C32	0.0799 (3)	0.9173 (3)	0.10955 (19)	0.0486 (8)
H32	0.0562	0.8551	0.1260	0.058*
C33	0.0002 (3)	1.0099 (3)	0.1083 (2)	0.0557 (8)
H33	−0.0776	1.0102	0.1262	0.067*
C34	0.0359 (3)	1.1012 (3)	0.0807 (2)	0.0597 (9)
H34	−0.0186	1.1621	0.0796	0.072*
C35	0.1506 (3)	1.1043 (3)	0.0546 (2)	0.0544 (8)
H35	0.1745	1.1657	0.0350	0.065*
C36	0.2280 (2)	1.0128 (2)	0.05867 (19)	0.0436 (7)
C37	0.3977 (3)	0.8980 (2)	0.04736 (19)	0.0435 (7)
C38	0.3255 (3)	0.7907 (3)	−0.0852 (2)	0.0652 (10)
H38A	0.2598	0.8447	−0.0864	0.098*
H38B	0.3297	0.7337	−0.1246	0.098*
H38C	0.3936	0.8179	−0.1061	0.098*
C39	0.4091 (3)	0.6689 (2)	0.0188 (2)	0.0525 (8)
H39A	0.4825	0.6880	−0.0054	0.063*
H39B	0.4093	0.6058	−0.0123	0.063*
C40	0.3840 (2)	0.6538 (2)	0.12194 (19)	0.0455 (7)
H40A	0.3273	0.6119	0.1362	0.055*	0.52 (3)
H40B	0.3296	0.6097	0.1375	0.055*	0.48 (3)
C41	0.4801 (7)	0.5954 (12)	0.1621 (9)	0.059 (6)	0.52 (3)
C42	0.5882 (8)	0.6182 (13)	0.1335 (10)	0.054 (5)	0.52 (3)
H42A	0.6025	0.6682	0.0891	0.065*	0.52 (3)
C43	0.6751 (8)	0.5662 (16)	0.1713 (14)	0.083 (7)	0.52 (3)
H43A	0.7474	0.5815	0.1522	0.099*	0.52 (3)
C44	0.6538 (12)	0.4915 (14)	0.2377 (15)	0.084 (7)	0.52 (3)
C45	0.5456 (14)	0.4686 (11)	0.2663 (12)	0.091 (6)	0.52 (3)
H45A	0.5314	0.4186	0.3107	0.109*	0.52 (3)
C46	0.4588 (10)	0.5206 (12)	0.2285 (11)	0.081 (7)	0.52 (3)
H46A	0.3864	0.5053	0.2476	0.097*	0.52 (3)
N6	0.7493 (14)	0.4540 (16)	0.2774 (17)	0.108 (6)	0.52 (3)
C47	0.8560 (14)	0.492 (2)	0.2421 (19)	0.144 (4)	0.52 (3)
H47A	0.8949	0.4622	0.1821	0.216*	0.52 (3)
H47B	0.9045	0.4708	0.2824	0.216*	0.52 (3)
H47C	0.8381	0.5664	0.2388	0.216*	0.52 (3)
C48	0.765 (2)	0.3442 (14)	0.3054 (19)	0.135 (4)	0.52 (3)
H48A	0.7009	0.3354	0.3545	0.202*	0.52 (3)
H48B	0.8340	0.3251	0.3255	0.202*	0.52 (3)
H48C	0.7718	0.3004	0.2543	0.202*	0.52 (3)
C41'	0.4856 (8)	0.6025 (11)	0.1575 (10)	0.047 (6)	0.48 (3)
C42'	0.5909 (8)	0.6311 (13)	0.1294 (11)	0.073 (7)	0.48 (3)
H42B	0.6007	0.6848	0.0880	0.088*	0.48 (3)
C43'	0.6814 (9)	0.5794 (15)	0.1633 (15)	0.073 (6)	0.48 (3)
H43B	0.7518	0.5985	0.1445	0.087*	0.48 (3)
C44'	0.6666 (12)	0.4991 (13)	0.2252 (16)	0.085 (7)	0.48 (3)
C45'	0.5614 (14)	0.4706 (10)	0.2532 (12)	0.073 (6)	0.48 (3)
H45B	0.5515	0.4169	0.2946	0.087*	0.48 (3)
C46'	0.4708 (10)	0.5223 (11)	0.2194 (10)	0.053 (5)	0.48 (3)
H46B	0.4004	0.5031	0.2381	0.064*	0.48 (3)
N6'	0.7550 (18)	0.4267 (17)	0.2554 (17)	0.115 (7)	0.48 (3)
C47'	0.8485 (17)	0.472 (2)	0.270 (2)	0.144 (4)	0.48 (3)
H47D	0.8160	0.5316	0.3112	0.216*	0.48 (3)
H47E	0.8913	0.4943	0.2125	0.216*	0.48 (3)
H47F	0.8985	0.4210	0.2961	0.216*	0.48 (3)
C48'	0.720 (2)	0.3476 (17)	0.3231 (17)	0.135 (4)	0.48 (3)
H48D	0.6980	0.2951	0.2941	0.202*	0.48 (3)
H48E	0.6572	0.3806	0.3722	0.202*	0.48 (3)
H48F	0.7838	0.3157	0.3472	0.202*	0.48 (3)
N7	1.0779 (4)	0.3506 (4)	0.9666 (5)	0.155 (2)
C49	0.9842 (5)	0.3741 (3)	0.9734 (3)	0.0864 (13)
C50	0.8635 (4)	0.4052 (4)	0.9821 (4)	0.127 (2)
H50A	0.8264	0.4441	1.0384	0.190*
H50B	0.8326	0.3443	0.9823	0.190*
H50C	0.8508	0.4481	0.9314	0.190*
N8	0.4299 (17)	0.2150 (15)	0.4534 (12)	0.228 (9)*	0.470 (13)
C51	0.4315 (15)	0.2384 (12)	0.5238 (11)	0.146 (6)*	0.470 (13)
C52	0.4488 (14)	0.3056 (13)	0.5951 (11)	0.152 (6)*	0.470 (13)
H52A	0.4806	0.3626	0.5658	0.228*	0.470 (13)
H52B	0.5003	0.2643	0.6267	0.228*	0.470 (13)
H52C	0.3765	0.3324	0.6381	0.228*	0.470 (13)
N8'	0.5004 (11)	0.2690 (10)	0.4335 (6)	0.174 (6)*	0.530 (13)
C51'	0.4772 (10)	0.2783 (10)	0.5106 (6)	0.115 (4)*	0.530 (13)
C52'	0.4250 (8)	0.2585 (8)	0.6089 (5)	0.085 (3)*	0.530 (13)
H52D	0.3435	0.2678	0.6195	0.128*	0.530 (13)
H52E	0.4411	0.3067	0.6469	0.128*	0.530 (13)
H52F	0.4566	0.1883	0.6233	0.128*	0.530 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0408 (4)	0.0531 (5)	0.0382 (4)	−0.0189 (3)	−0.0038 (3)	−0.0045 (3)
O1	0.0551 (13)	0.0666 (14)	0.0369 (11)	−0.0328 (11)	−0.0106 (10)	0.0003 (10)
O2	0.0431 (13)	0.0556 (13)	0.0587 (14)	−0.0145 (11)	−0.0004 (10)	0.0081 (10)
N1	0.0487 (14)	0.0432 (14)	0.0314 (13)	−0.0123 (11)	−0.0014 (11)	−0.0056 (10)
N2	0.0370 (13)	0.0487 (14)	0.0369 (13)	−0.0105 (11)	−0.0077 (10)	−0.0059 (11)
N3	0.0387 (13)	0.0414 (13)	0.0296 (12)	−0.0137 (10)	−0.0064 (10)	−0.0019 (10)
N4	0.0478 (16)	0.0444 (16)	0.0511 (16)	−0.0175 (14)	−0.0031 (12)	0.0068 (12)
N5	0.0556 (16)	0.0479 (15)	0.0319 (13)	−0.0085 (12)	−0.0061 (11)	−0.0054 (11)
C1	0.0520 (19)	0.057 (2)	0.0385 (17)	−0.0079 (16)	0.0040 (14)	−0.0104 (14)
C2	0.043 (5)	0.064 (6)	0.024 (5)	−0.009 (4)	0.000 (4)	−0.008 (4)
C3	0.078 (7)	0.055 (5)	0.083 (7)	−0.027 (5)	−0.020 (5)	0.005 (5)
C4	0.157 (13)	0.073 (7)	0.081 (8)	−0.044 (8)	−0.018 (7)	0.006 (6)
C5	0.084 (11)	0.098 (10)	0.105 (9)	−0.052 (9)	0.021 (8)	−0.011 (7)
C6	0.045 (7)	0.082 (10)	0.177 (14)	−0.036 (6)	0.014 (8)	−0.015 (10)
C7	0.038 (6)	0.100 (8)	0.109 (8)	−0.009 (5)	−0.014 (6)	−0.023 (7)
C2'	0.044 (5)	0.050 (5)	0.043 (4)	0.001 (4)	−0.003 (4)	−0.014 (4)
C3'	0.081 (7)	0.069 (6)	0.051 (6)	−0.022 (6)	−0.016 (4)	0.003 (4)
C4'	0.143 (15)	0.074 (8)	0.087 (8)	−0.056 (10)	−0.003 (8)	0.004 (6)
C5'	0.111 (11)	0.071 (9)	0.097 (9)	−0.047 (10)	0.033 (9)	−0.031 (7)
C6'	0.063 (7)	0.156 (12)	0.129 (12)	−0.034 (8)	0.007 (7)	−0.042 (9)
C7'	0.055 (6)	0.110 (8)	0.093 (7)	−0.008 (5)	−0.011 (5)	−0.024 (6)
C8	0.0551 (19)	0.0436 (17)	0.0363 (16)	−0.0109 (15)	−0.0072 (14)	−0.0066 (13)
C9	0.0461 (17)	0.0400 (16)	0.0369 (16)	−0.0084 (13)	−0.0101 (13)	−0.0033 (13)
C10	0.0492 (19)	0.057 (2)	0.0468 (18)	−0.0129 (15)	−0.0101 (14)	−0.0113 (15)
C11	0.060 (2)	0.065 (2)	0.0491 (19)	−0.0264 (18)	−0.0129 (16)	−0.0089 (16)
C12	0.093 (3)	0.085 (3)	0.085 (3)	−0.028 (2)	−0.047 (2)	−0.010 (2)
C13	0.146 (5)	0.114 (4)	0.089 (3)	−0.066 (4)	−0.069 (3)	0.008 (3)
C14	0.148 (5)	0.127 (4)	0.058 (3)	−0.090 (4)	−0.015 (3)	−0.017 (3)
C15	0.095 (3)	0.099 (3)	0.086 (3)	−0.052 (3)	0.015 (3)	−0.047 (3)
C16	0.067 (2)	0.076 (3)	0.074 (3)	−0.023 (2)	−0.0089 (19)	−0.028 (2)
C17	0.0400 (16)	0.0405 (16)	0.0324 (15)	−0.0061 (13)	−0.0061 (12)	−0.0019 (12)
C18	0.0410 (16)	0.0370 (15)	0.0320 (14)	−0.0077 (13)	−0.0058 (12)	−0.0015 (12)
C19	0.0468 (17)	0.0471 (17)	0.0350 (16)	−0.0135 (14)	−0.0044 (13)	−0.0040 (13)
C20	0.0363 (15)	0.0446 (16)	0.0309 (14)	−0.0127 (13)	−0.0029 (12)	−0.0026 (12)
C21	0.0555 (19)	0.0391 (16)	0.0339 (15)	−0.0132 (15)	0.0009 (14)	−0.0036 (13)
C22	0.081 (3)	0.056 (2)	0.098 (3)	−0.015 (2)	−0.033 (2)	0.018 (2)
C23	0.108 (4)	0.065 (3)	0.125 (4)	0.005 (3)	−0.027 (3)	0.028 (3)
C24	0.165 (5)	0.041 (2)	0.083 (3)	−0.010 (3)	0.004 (3)	0.000 (2)
C25	0.193 (6)	0.059 (3)	0.087 (3)	−0.059 (3)	−0.030 (4)	−0.001 (2)
C26	0.116 (3)	0.057 (2)	0.070 (2)	−0.041 (2)	−0.030 (2)	0.0034 (19)
C27	0.0353 (15)	0.0366 (15)	0.0377 (16)	−0.0080 (12)	−0.0085 (12)	−0.0012 (12)
C28	0.0430 (16)	0.0401 (16)	0.0323 (15)	−0.0139 (13)	−0.0080 (12)	0.0008 (12)
C29	0.0421 (16)	0.0415 (16)	0.0325 (15)	−0.0156 (13)	−0.0063 (12)	−0.0002 (12)
C30	0.0432 (16)	0.0416 (16)	0.0317 (15)	−0.0135 (13)	−0.0030 (12)	−0.0015 (12)
C31	0.0444 (17)	0.0460 (17)	0.0284 (14)	−0.0102 (14)	−0.0057 (12)	−0.0028 (12)
C32	0.0509 (19)	0.057 (2)	0.0396 (17)	−0.0174 (16)	−0.0097 (14)	−0.0011 (14)
C33	0.0463 (19)	0.070 (2)	0.0498 (19)	−0.0085 (17)	−0.0146 (15)	−0.0007 (17)
C34	0.056 (2)	0.061 (2)	0.056 (2)	0.0020 (17)	−0.0155 (16)	−0.0023 (17)
C35	0.066 (2)	0.0489 (19)	0.0437 (18)	−0.0078 (17)	−0.0097 (16)	0.0006 (15)
C36	0.0463 (18)	0.0462 (18)	0.0343 (16)	−0.0091 (14)	−0.0044 (13)	−0.0023 (13)
C37	0.0451 (18)	0.0465 (19)	0.0345 (16)	−0.0137 (15)	−0.0003 (13)	0.0008 (13)
C38	0.083 (3)	0.072 (2)	0.0348 (17)	−0.0106 (19)	−0.0094 (17)	−0.0052 (16)
C39	0.058 (2)	0.0492 (19)	0.0447 (18)	−0.0066 (16)	−0.0066 (15)	−0.0101 (14)
C40	0.0522 (18)	0.0395 (17)	0.0426 (17)	−0.0129 (14)	−0.0062 (14)	−0.0032 (13)
C41	0.035 (9)	0.061 (11)	0.078 (13)	−0.013 (8)	−0.004 (7)	−0.032 (9)
C42	0.056 (11)	0.044 (6)	0.046 (8)	−0.002 (6)	0.005 (7)	0.014 (6)
C43	0.054 (10)	0.100 (14)	0.086 (13)	−0.018 (10)	−0.001 (9)	−0.002 (11)
C44	0.114 (16)	0.057 (10)	0.071 (8)	0.022 (9)	−0.044 (10)	0.008 (8)
C45	0.078 (9)	0.094 (12)	0.092 (12)	0.002 (8)	−0.030 (8)	0.035 (9)
C46	0.108 (13)	0.076 (14)	0.060 (9)	−0.008 (10)	−0.037 (9)	0.016 (8)
N6	0.105 (10)	0.091 (10)	0.138 (14)	0.008 (7)	−0.071 (8)	−0.003 (10)
C47	0.123 (5)	0.177 (8)	0.149 (10)	−0.008 (5)	−0.089 (6)	0.034 (7)
C48	0.122 (10)	0.142 (5)	0.133 (7)	0.028 (6)	−0.069 (8)	0.020 (5)
C41'	0.076 (14)	0.031 (8)	0.027 (8)	0.001 (8)	−0.011 (7)	0.013 (7)
C42'	0.053 (12)	0.067 (10)	0.101 (15)	−0.009 (8)	−0.026 (9)	−0.017 (8)
C43'	0.067 (11)	0.053 (7)	0.090 (13)	0.014 (8)	−0.028 (10)	−0.004 (8)
C44'	0.053 (9)	0.109 (19)	0.089 (13)	−0.003 (10)	−0.018 (9)	−0.026 (12)
C45'	0.122 (15)	0.047 (9)	0.050 (6)	−0.020 (9)	−0.023 (9)	0.008 (5)
C46'	0.054 (8)	0.041 (10)	0.057 (8)	−0.019 (7)	0.003 (7)	0.006 (7)
N6'	0.140 (13)	0.086 (11)	0.121 (12)	0.017 (8)	−0.069 (9)	−0.011 (10)
C47'	0.123 (5)	0.177 (8)	0.149 (10)	−0.008 (5)	−0.089 (6)	0.034 (7)
C48'	0.122 (10)	0.142 (5)	0.133 (7)	0.028 (6)	−0.069 (8)	0.020 (5)
N7	0.110 (4)	0.102 (4)	0.246 (7)	−0.022 (3)	−0.039 (4)	0.009 (4)
C49	0.099 (4)	0.062 (3)	0.098 (3)	−0.030 (3)	−0.014 (3)	−0.006 (2)
C50	0.106 (4)	0.112 (4)	0.171 (6)	−0.036 (3)	−0.037 (4)	−0.049 (4)

Geometric parameters (Å, º) top

S1—C27	1.742 (3)	C25—H25	0.9300
S1—C29	1.826 (3)	C26—H26	0.9300
O1—C28	1.215 (3)	C28—C29	1.529 (4)
O2—C37	1.230 (3)	C29—C30	1.569 (4)
N1—C19	1.455 (3)	C29—C40	1.595 (4)
N1—C8	1.463 (4)	C30—C31	1.518 (4)
N1—C1	1.465 (3)	C30—C37	1.565 (4)
N2—C27	1.276 (3)	C31—C32	1.386 (4)
N2—C17	1.426 (3)	C31—C36	1.387 (4)
N3—C28	1.370 (3)	C32—C33	1.392 (4)
N3—C27	1.384 (3)	C32—H32	0.9300
N3—C20	1.481 (3)	C33—C34	1.376 (5)
N4—C37	1.340 (4)	C33—H33	0.9300
N4—C36	1.404 (4)	C34—C35	1.382 (5)
N4—H4	0.83 (3)	C34—H34	0.9300
N5—C39	1.459 (4)	C35—C36	1.373 (4)
N5—C38	1.462 (4)	C35—H35	0.9300
N5—C30	1.467 (3)	C38—H38A	0.9600
C1—C2'	1.468 (4)	C38—H38B	0.9600
C1—C2	1.563 (4)	C38—H38C	0.9600
C1—H1A	0.9600	C39—C40	1.523 (4)
C1—H1B	0.9600	C39—H39A	0.9700
C1—H1C	0.9600	C39—H39B	0.9700
C1—H1D	0.9600	C40—C41'	1.514 (6)
C2—C3	1.3900	C40—C41	1.526 (6)
C2—C7	1.3900	C40—H40A	0.9601
C3—C4	1.3900	C40—H40B	0.9600
C3—H3A	0.9300	C41—C42	1.3900
C4—C5	1.3900	C41—C46	1.3900
C4—H4A	0.9300	C42—C43	1.3900
C5—C6	1.3900	C42—H42A	0.9300
C5—H5A	0.9300	C43—C44	1.3900
C6—C7	1.3900	C43—H43A	0.9300
C6—H6A	0.9300	C44—C45	1.3900
C7—H7A	0.9300	C44—N6	1.454 (13)
C2'—C3'	1.3900	C45—C46	1.3900
C2'—C7'	1.3900	C45—H45A	0.9300
C3'—C4'	1.3900	C46—H46A	0.9300
C3'—H3'A	0.9300	N6—C48	1.471 (15)
C4'—C5'	1.3900	N6—C47	1.473 (16)
C4'—H4'A	0.9300	C47—H47A	0.9600
C5'—C6'	1.3900	C47—H47B	0.9600
C5'—H5'A	0.9300	C47—H47C	0.9600
C6'—C7'	1.3900	C48—H48A	0.9600
C6'—H6'A	0.9300	C48—H48B	0.9600
C7'—H7'A	0.9300	C48—H48C	0.9600
C8—C9	1.497 (4)	C41'—C42'	1.3900
C8—H8A	0.9700	C41'—C46'	1.3900
C8—H8B	0.9700	C42'—C43'	1.3900
C9—C10	1.337 (4)	C42'—H42B	0.9300
C9—C17	1.472 (4)	C43'—C44'	1.3900
C10—C11	1.477 (4)	C43'—H43B	0.9300
C10—H10	0.9300	C44'—C45'	1.3900
C11—C16	1.377 (5)	C44'—N6'	1.447 (15)
C11—C12	1.389 (5)	C45'—C46'	1.3900
C12—C13	1.390 (6)	C45'—H45B	0.9300
C12—H12	0.9300	C46'—H46B	0.9300
C13—C14	1.354 (7)	N6'—C48'	1.478 (17)
C13—H13	0.9300	N6'—C47'	1.488 (16)
C14—C15	1.370 (7)	C47'—H47D	0.9600
C14—H14	0.9300	C47'—H47E	0.9600
C15—C16	1.388 (5)	C47'—H47F	0.9600
C15—H15	0.9300	C48'—H48D	0.9600
C16—H16	0.9300	C48'—H48E	0.9600
C17—C18	1.342 (4)	C48'—H48F	0.9600
C18—C19	1.494 (4)	N7—C49	1.113 (5)
C18—C20	1.507 (4)	C49—C50	1.435 (5)
C19—H19A	0.9700	C50—H50A	0.9600
C19—H19B	0.9700	C50—H50B	0.9600
C20—C21	1.517 (4)	C50—H50C	0.9600
C20—H20	0.9800	N8—C51	1.129 (9)
C21—C22	1.361 (5)	C51—C52	1.510 (9)
C21—C26	1.371 (4)	C52—H52A	0.9600
C22—C23	1.387 (6)	C52—H52B	0.9600
C22—H22	0.9300	C52—H52C	0.9600
C23—C24	1.353 (7)	N8'—C51'	1.131 (8)
C23—H23	0.9300	C51'—C52'	1.493 (8)
C24—C25	1.344 (7)	C52'—H52D	0.9600
C24—H24	0.9300	C52'—H52E	0.9600
C25—C26	1.384 (6)	C52'—H52F	0.9600

C27—S1—C29	93.47 (12)	C30—C29—C40	104.3 (2)
C19—N1—C8	112.1 (2)	C28—C29—S1	105.12 (18)
C19—N1—C1	110.0 (2)	C30—C29—S1	111.30 (18)
C8—N1—C1	108.4 (2)	C40—C29—S1	115.96 (19)
C27—N2—C17	115.7 (2)	N5—C30—C31	113.0 (2)
C28—N3—C27	116.9 (2)	N5—C30—C37	111.0 (2)
C28—N3—C20	121.2 (2)	C31—C30—C37	100.8 (2)
C27—N3—C20	120.3 (2)	N5—C30—C29	102.7 (2)
C37—N4—C36	112.0 (3)	C31—C30—C29	119.6 (2)
C37—N4—H4	123 (2)	C37—C30—C29	109.9 (2)
C36—N4—H4	125 (2)	C32—C31—C36	119.1 (3)
C39—N5—C38	114.8 (2)	C32—C31—C30	131.9 (3)
C39—N5—C30	106.6 (2)	C36—C31—C30	108.9 (2)
C38—N5—C30	115.7 (2)	C31—C32—C33	118.8 (3)
N1—C1—C2'	118.6 (3)	C31—C32—H32	120.6
N1—C1—C2	110.1 (3)	C33—C32—H32	120.6
C2'—C1—C2	16.0	C34—C33—C32	120.4 (3)
N1—C1—H1A	109.6	C34—C33—H33	119.8
C2'—C1—H1A	93.7	C32—C33—H33	119.8
C2—C1—H1A	109.6	C33—C34—C35	121.5 (3)
N1—C1—H1B	109.5	C33—C34—H34	119.2
C2'—C1—H1B	115.5	C35—C34—H34	119.2
C2—C1—H1B	109.8	C36—C35—C34	117.3 (3)
H1A—C1—H1B	108.3	C36—C35—H35	121.4
N1—C1—H1C	109.6	C34—C35—H35	121.4
C2'—C1—H1C	93.7	C35—C36—C31	122.8 (3)
C2—C1—H1C	109.6	C35—C36—N4	127.4 (3)
H1A—C1—H1C	0.0	C31—C36—N4	109.8 (3)
H1B—C1—H1C	108.3	O2—C37—N4	126.2 (3)
N1—C1—H1D	109.5	O2—C37—C30	125.5 (3)
C2'—C1—H1D	115.5	N4—C37—C30	108.3 (3)
C2—C1—H1D	109.8	N5—C38—H38A	109.5
H1A—C1—H1D	108.3	N5—C38—H38B	109.5
H1B—C1—H1D	0.0	H38A—C38—H38B	109.5
H1C—C1—H1D	108.3	N5—C38—H38C	109.5
C3—C2—C7	120.0	H38A—C38—H38C	109.5
C3—C2—C1	122.2 (3)	H38B—C38—H38C	109.5
C7—C2—C1	117.5 (3)	N5—C39—C40	103.8 (2)
C4—C3—C2	120.0	N5—C39—H39A	111.0
C4—C3—H3A	120.0	C40—C39—H39A	111.0
C2—C3—H3A	120.0	N5—C39—H39B	111.0
C5—C4—C3	120.0	C40—C39—H39B	111.0
C5—C4—H4A	120.0	H39A—C39—H39B	109.0
C3—C4—H4A	120.0	C41'—C40—C39	116.0 (6)
C4—C5—C6	120.0	C41'—C40—C41	5.1 (7)
C4—C5—H5A	120.0	C39—C40—C41	119.0 (6)
C6—C5—H5A	120.0	C41'—C40—C29	115.9 (7)
C7—C6—C5	120.0	C39—C40—C29	103.6 (2)
C7—C6—H6A	120.0	C41—C40—C29	117.6 (7)
C5—C6—H6A	120.0	C41'—C40—H40A	110.0
C6—C7—C2	120.0	C39—C40—H40A	105.1
C6—C7—H7A	120.0	C41—C40—H40A	105.0
C2—C7—H7A	120.0	C29—C40—H40A	105.1
C3'—C2'—C7'	120.0	C41'—C40—H40B	107.4
C3'—C2'—C1	115.4 (3)	C39—C40—H40B	106.6
C7'—C2'—C1	124.2 (3)	C41—C40—H40B	102.4
C4'—C3'—C2'	120.0	C29—C40—H40B	106.6
C4'—C3'—H3'A	120.0	H40A—C40—H40B	2.6
C2'—C3'—H3'A	120.0	C42—C41—C46	120.0
C3'—C4'—C5'	120.0	C42—C41—C40	120.0 (6)
C3'—C4'—H4'A	120.0	C46—C41—C40	119.9 (6)
C5'—C4'—H4'A	120.0	C43—C42—C41	120.0
C6'—C5'—C4'	120.0	C43—C42—H42A	120.0
C6'—C5'—H5'A	120.0	C41—C42—H42A	120.0
C4'—C5'—H5'A	120.0	C42—C43—C44	120.0
C5'—C6'—C7'	120.0	C42—C43—H43A	120.0
C5'—C6'—H6'A	120.0	C44—C43—H43A	120.0
C7'—C6'—H6'A	120.0	C45—C44—C43	120.0
C6'—C7'—C2'	120.0	C45—C44—N6	126.9 (11)
C6'—C7'—H7'A	120.0	C43—C44—N6	112.7 (11)
C2'—C7'—H7'A	120.0	C44—C45—C46	120.0
N1—C8—C9	113.7 (2)	C44—C45—H45A	120.0
N1—C8—H8A	108.8	C46—C45—H45A	120.0
C9—C8—H8A	108.8	C45—C46—C41	120.0
N1—C8—H8B	108.8	C45—C46—H46A	120.0
C9—C8—H8B	108.8	C41—C46—H46A	120.0
H8A—C8—H8B	107.7	C44—N6—C48	115.7 (12)
C10—C9—C17	121.1 (3)	C44—N6—C47	119.6 (13)
C10—C9—C8	124.7 (3)	C48—N6—C47	114.8 (14)
C17—C9—C8	114.2 (2)	N6—C47—H47A	109.5
C9—C10—C11	127.7 (3)	N6—C47—H47B	109.5
C9—C10—H10	116.1	H47A—C47—H47B	109.5
C11—C10—H10	116.1	N6—C47—H47C	109.5
C16—C11—C12	117.3 (3)	H47A—C47—H47C	109.5
C16—C11—C10	123.8 (3)	H47B—C47—H47C	109.5
C12—C11—C10	118.9 (3)	N6—C48—H48A	109.5
C11—C12—C13	120.8 (4)	N6—C48—H48B	109.5
C11—C12—H12	119.6	H48A—C48—H48B	109.5
C13—C12—H12	119.6	N6—C48—H48C	109.5
C14—C13—C12	120.9 (5)	H48A—C48—H48C	109.5
C14—C13—H13	119.5	H48B—C48—H48C	109.5
C12—C13—H13	119.5	C42'—C41'—C46'	120.0
C13—C14—C15	119.2 (4)	C42'—C41'—C40	122.9 (6)
C13—C14—H14	120.4	C46'—C41'—C40	117.1 (6)
C15—C14—H14	120.4	C41'—C42'—C43'	120.0
C14—C15—C16	120.4 (4)	C41'—C42'—H42B	120.0
C14—C15—H15	119.8	C43'—C42'—H42B	120.0
C16—C15—H15	119.8	C44'—C43'—C42'	120.0
C11—C16—C15	121.4 (4)	C44'—C43'—H43B	120.0
C11—C16—H16	119.3	C42'—C43'—H43B	120.0
C15—C16—H16	119.3	C43'—C44'—C45'	120.0
C18—C17—N2	123.0 (2)	C43'—C44'—N6'	127.0 (13)
C18—C17—C9	120.6 (2)	C45'—C44'—N6'	112.2 (12)
N2—C17—C9	116.4 (2)	C44'—C45'—C46'	120.0
C17—C18—C19	123.2 (2)	C44'—C45'—H45B	120.0
C17—C18—C20	121.4 (2)	C46'—C45'—H45B	120.0
C19—C18—C20	115.4 (2)	C45'—C46'—C41'	120.0
N1—C19—C18	113.4 (2)	C45'—C46'—H46B	120.0
N1—C19—H19A	108.9	C41'—C46'—H46B	120.0
C18—C19—H19A	108.9	C44'—N6'—C48'	118.4 (15)
N1—C19—H19B	108.9	C44'—N6'—C47'	115.2 (13)
C18—C19—H19B	108.9	C48'—N6'—C47'	114.2 (15)
H19A—C19—H19B	107.7	N6'—C47'—H47D	109.5
N3—C20—C18	107.8 (2)	N6'—C47'—H47E	109.5
N3—C20—C21	110.2 (2)	H47D—C47'—H47E	109.5
C18—C20—C21	113.2 (2)	N6'—C47'—H47F	109.5
N3—C20—H20	108.5	H47D—C47'—H47F	109.5
C18—C20—H20	108.5	H47E—C47'—H47F	109.5
C21—C20—H20	108.5	N6'—C48'—H48D	109.5
C22—C21—C26	118.7 (3)	N6'—C48'—H48E	109.5
C22—C21—C20	120.5 (3)	H48D—C48'—H48E	109.5
C26—C21—C20	120.8 (3)	N6'—C48'—H48F	109.5
C21—C22—C23	120.3 (4)	H48D—C48'—H48F	109.5
C21—C22—H22	119.9	H48E—C48'—H48F	109.5
C23—C22—H22	119.9	N7—C49—C50	179.6 (6)
C24—C23—C22	120.9 (5)	C49—C50—H50A	109.5
C24—C23—H23	119.6	C49—C50—H50B	109.5
C22—C23—H23	119.6	H50A—C50—H50B	109.5
C25—C24—C23	118.9 (4)	C49—C50—H50C	109.5
C25—C24—H24	120.6	H50A—C50—H50C	109.5
C23—C24—H24	120.6	H50B—C50—H50C	109.5
C24—C25—C26	121.4 (5)	N8—C51—C52	157 (2)
C24—C25—H25	119.3	C51—C52—H52A	109.5
C26—C25—H25	119.3	C51—C52—H52B	109.5
C21—C26—C25	119.9 (4)	H52A—C52—H52B	109.5
C21—C26—H26	120.1	C51—C52—H52C	109.5
C25—C26—H26	120.1	H52A—C52—H52C	109.5
N2—C27—N3	125.9 (2)	H52B—C52—H52C	109.5
N2—C27—S1	122.7 (2)	N8'—C51'—C52'	158.5 (15)
N3—C27—S1	111.36 (19)	C51'—C52'—H52D	109.5
O1—C28—N3	122.6 (2)	C51'—C52'—H52E	109.5
O1—C28—C29	124.4 (2)	H52D—C52'—H52E	109.5
N3—C28—C29	113.0 (2)	C51'—C52'—H52F	109.5
C28—C29—C30	113.4 (2)	H52D—C52'—H52F	109.5
C28—C29—C40	106.9 (2)	H52E—C52'—H52F	109.5

C19—N1—C1—C2'	61.5 (6)	C27—S1—C29—C40	−114.4 (2)
C8—N1—C1—C2'	−175.6 (5)	C39—N5—C30—C31	−170.7 (2)
C19—N1—C1—C2	76.3 (4)	C38—N5—C30—C31	60.4 (3)
C8—N1—C1—C2	−160.8 (4)	C39—N5—C30—C37	76.9 (3)
N1—C1—C2—C3	51.3 (5)	C38—N5—C30—C37	−52.1 (3)
C2'—C1—C2—C3	176.51 (6)	C39—N5—C30—C29	−40.5 (3)
N1—C1—C2—C7	−135.4 (4)	C38—N5—C30—C29	−169.5 (2)
C2'—C1—C2—C7	−10.1 (2)	C28—C29—C30—N5	−95.6 (3)
C7—C2—C3—C4	0.0	C40—C29—C30—N5	20.4 (3)
C1—C2—C3—C4	173.2 (3)	S1—C29—C30—N5	146.13 (18)
C2—C3—C4—C5	0.0	C28—C29—C30—C31	30.4 (3)
C3—C4—C5—C6	0.0	C40—C29—C30—C31	146.4 (2)
C4—C5—C6—C7	0.0	S1—C29—C30—C31	−87.9 (3)
C5—C6—C7—C2	0.0	C28—C29—C30—C37	146.2 (2)
C3—C2—C7—C6	0.0	C40—C29—C30—C37	−97.8 (2)
C1—C2—C7—C6	−173.5 (3)	S1—C29—C30—C37	27.9 (3)
N1—C1—C2'—C3'	66.2 (6)	N5—C30—C31—C32	60.9 (4)
C2—C1—C2'—C3'	5.32 (9)	C37—C30—C31—C32	179.4 (3)
N1—C1—C2'—C7'	−120.5 (5)	C29—C30—C31—C32	−60.1 (4)
C2—C1—C2'—C7'	178.57 (18)	N5—C30—C31—C36	−114.9 (3)
C7'—C2'—C3'—C4'	0.0	C37—C30—C31—C36	3.6 (3)
C1—C2'—C3'—C4'	173.6 (3)	C29—C30—C31—C36	124.1 (3)
C2'—C3'—C4'—C5'	0.0	C36—C31—C32—C33	−2.3 (4)
C3'—C4'—C5'—C6'	0.0	C30—C31—C32—C33	−177.8 (3)
C4'—C5'—C6'—C7'	0.0	C31—C32—C33—C34	2.4 (5)
C5'—C6'—C7'—C2'	0.0	C32—C33—C34—C35	−0.7 (5)
C3'—C2'—C7'—C6'	0.0	C33—C34—C35—C36	−1.1 (5)
C1—C2'—C7'—C6'	−173.0 (3)	C34—C35—C36—C31	1.2 (4)
C19—N1—C8—C9	−56.2 (3)	C34—C35—C36—N4	179.9 (3)
C1—N1—C8—C9	−177.8 (2)	C32—C31—C36—C35	0.5 (4)
N1—C8—C9—C10	−140.2 (3)	C30—C31—C36—C35	176.9 (3)
N1—C8—C9—C17	39.6 (3)	C32—C31—C36—N4	−178.4 (2)
C17—C9—C10—C11	−179.1 (3)	C30—C31—C36—N4	−2.0 (3)
C8—C9—C10—C11	0.7 (5)	C37—N4—C36—C35	−179.8 (3)
C9—C10—C11—C16	−44.2 (5)	C37—N4—C36—C31	−0.9 (3)
C9—C10—C11—C12	137.2 (4)	C36—N4—C37—O2	−178.9 (3)
C16—C11—C12—C13	1.5 (6)	C36—N4—C37—C30	3.3 (3)
C10—C11—C12—C13	−179.8 (4)	N5—C30—C37—O2	−62.0 (4)
C11—C12—C13—C14	−1.7 (7)	C31—C30—C37—O2	178.1 (3)
C12—C13—C14—C15	1.2 (7)	C29—C30—C37—O2	50.9 (4)
C13—C14—C15—C16	−0.6 (7)	N5—C30—C37—N4	115.8 (3)
C12—C11—C16—C15	−0.9 (5)	C31—C30—C37—N4	−4.1 (3)
C10—C11—C16—C15	−179.5 (3)	C29—C30—C37—N4	−131.3 (2)
C14—C15—C16—C11	0.4 (6)	C38—N5—C39—C40	174.3 (3)
C27—N2—C17—C18	11.3 (4)	C30—N5—C39—C40	44.8 (3)
C27—N2—C17—C9	−166.2 (2)	N5—C39—C40—C41'	−157.3 (7)
C10—C9—C17—C18	167.9 (3)	N5—C39—C40—C41	−161.8 (7)
C8—C9—C17—C18	−11.9 (4)	N5—C39—C40—C29	−29.0 (3)
C10—C9—C17—N2	−14.5 (4)	C28—C29—C40—C41'	−106.2 (5)
C8—C9—C17—N2	165.7 (2)	C30—C29—C40—C41'	133.3 (5)
N2—C17—C18—C19	−176.9 (3)	S1—C29—C40—C41'	10.6 (5)
C9—C17—C18—C19	0.6 (4)	C28—C29—C40—C39	125.5 (2)
N2—C17—C18—C20	3.6 (4)	C30—C29—C40—C39	5.1 (3)
C9—C17—C18—C20	−178.9 (2)	S1—C29—C40—C39	−117.7 (2)
C8—N1—C19—C18	43.4 (3)	C28—C29—C40—C41	−100.9 (5)
C1—N1—C19—C18	164.1 (2)	C30—C29—C40—C41	138.7 (5)
C17—C18—C19—N1	−16.5 (4)	S1—C29—C40—C41	15.9 (5)
C20—C18—C19—N1	163.0 (2)	C41'—C40—C41—C42	−9 (15)
C28—N3—C20—C18	−168.2 (2)	C39—C40—C41—C42	45.5 (14)
C27—N3—C20—C18	26.7 (3)	C29—C40—C41—C42	−80.9 (12)
C28—N3—C20—C21	67.7 (3)	C41'—C40—C41—C46	170 (16)
C27—N3—C20—C21	−97.4 (3)	C39—C40—C41—C46	−135.6 (8)
C17—C18—C20—N3	−21.2 (4)	C29—C40—C41—C46	98.0 (10)
C19—C18—C20—N3	159.3 (2)	C46—C41—C42—C43	0.0
C17—C18—C20—C21	101.0 (3)	C40—C41—C42—C43	178.9 (15)
C19—C18—C20—C21	−78.5 (3)	C41—C42—C43—C44	0.0
N3—C20—C21—C22	72.9 (4)	C42—C43—C44—C45	0.0
C18—C20—C21—C22	−47.9 (4)	C42—C43—C44—N6	−173 (2)
N3—C20—C21—C26	−105.0 (3)	C43—C44—C45—C46	0.0
C18—C20—C21—C26	134.1 (3)	N6—C44—C45—C46	172 (2)
C26—C21—C22—C23	0.8 (6)	C44—C45—C46—C41	0.0
C20—C21—C22—C23	−177.2 (3)	C42—C41—C46—C45	0.0
C21—C22—C23—C24	−1.8 (7)	C40—C41—C46—C45	−178.9 (15)
C22—C23—C24—C25	1.7 (8)	C45—C44—N6—C48	40 (3)
C23—C24—C25—C26	−0.8 (8)	C43—C44—N6—C48	−147 (2)
C22—C21—C26—C25	0.1 (5)	C45—C44—N6—C47	−176.0 (19)
C20—C21—C26—C25	178.1 (3)	C43—C44—N6—C47	−3 (3)
C24—C25—C26—C21	−0.2 (7)	C39—C40—C41'—C42'	45.6 (13)
C17—N2—C27—N3	−5.5 (4)	C41—C40—C41'—C42'	174 (16)
C17—N2—C27—S1	171.8 (2)	C29—C40—C41'—C42'	−76.3 (12)
C28—N3—C27—N2	179.0 (3)	C39—C40—C41'—C46'	−133.0 (8)
C20—N3—C27—N2	−15.2 (4)	C41—C40—C41'—C46'	−5 (15)
C28—N3—C27—S1	1.5 (3)	C29—C40—C41'—C46'	105.1 (9)
C20—N3—C27—S1	167.24 (19)	C46'—C41'—C42'—C43'	0.0
C29—S1—C27—N2	179.4 (2)	C40—C41'—C42'—C43'	−178.6 (16)
C29—S1—C27—N3	−3.0 (2)	C41'—C42'—C43'—C44'	0.0
C27—N3—C28—O1	177.6 (3)	C42'—C43'—C44'—C45'	0.0
C20—N3—C28—O1	12.0 (4)	C42'—C43'—C44'—N6'	169 (2)
C27—N3—C28—C29	1.3 (3)	C43'—C44'—C45'—C46'	0.0
C20—N3—C28—C29	−164.3 (2)	N6'—C44'—C45'—C46'	−171 (2)
O1—C28—C29—C30	58.7 (4)	C44'—C45'—C46'—C41'	0.0
N3—C28—C29—C30	−125.1 (2)	C42'—C41'—C46'—C45'	0.0
O1—C28—C29—C40	−55.7 (4)	C40—C41'—C46'—C45'	178.7 (15)
N3—C28—C29—C40	120.5 (2)	C43'—C44'—N6'—C48'	179.1 (18)
O1—C28—C29—S1	−179.4 (2)	C45'—C44'—N6'—C48'	−11 (3)
N3—C28—C29—S1	−3.3 (3)	C43'—C44'—N6'—C47'	39 (3)
C27—S1—C29—C28	3.4 (2)	C45'—C44'—N6'—C47'	−151 (2)
C27—S1—C29—C30	126.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O2ⁱ	0.83 (3)	2.06 (3)	2.885 (3)	169 (3)

Symmetry code: (i) −x+1, −y+2, −z.

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