2-(p-Methoxy­phenyl)-3-[o-(methyl­amino­thio­carbonyl)­phenyl]-1,3,2-ox­aza­phospho­lidine 2-sulfide

In the title compound, C₁₇H₁₉N₂O₂PS₂, the five-membered phospho­rus heterocycle has an envelope conformation. The carb­amide moiety is involved in an N—H...S intramolecular hydrogen bond. The existence of a d–p π bond between the P atom and the adjacent N atom is observed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.045
• wR factor = 0.103
• Data-to-parameter ratio = 11.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_601  Alert C Structure Contains Solvent Accessible VOIDS of      46.00 A   3

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.03
         From the CIF: _reflns_number_total              10230
         Count of symmetry unique reflns         6733
         Completeness (_total/calc)            151.94%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      3497
         Fraction of Friedel pairs measured     0.519
         Are heavy atom types Z>Si present          yes
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

The title compound, (2), was synthesized through thiation and regioselective cyclization of multifuctional 2-[N-(2-hydroxy)ethyl]amino-N'-methylbenzamide, (1), with Lawesson's reagent in one pot procedure. This compound exhibits moderate herbicidal activity under the concentration of 100 p.p.m. in preliminary bioassays. In spite of a full characterization of the structure by spectroscopic and microanalytical methods, compound (2) is necessarily subjected to X-ray diffraction analysis for the purpose of structure–activity study. The molecule consists of two phenyl rings and one five-membered phosphorus heterocycle bearing an O—P—N moiety, which confers potential bioactivity of this structure in comparison with numerous P–O– or P–N-containing molecules of pharmaceutical or agricultural importance (Brassfield et al., 1975; Gilard et al., 1999; Darrow et al., 1994; Morita et al., 1987; Deng et al., 2001).

There are four independent molecules in the crystal and the molecular structure of one of these molecules is shown in Fig. 1. The five-membered ring exists in an envelope conformation and atom C10 deviates from the plane defined by atoms P1, N1, O1 and C9. Further investigation of the bond-length data reveals that there exists d–p π-bond properties between the P and N atoms due to the evidently shorter bond length [1.653 (5)–1.668 (5) Å] than that of a single normal P—N bond (1.76 Å) based on Riess's theory (Riess, 1986). In addition, the thiocarbamide N atom interacts moderately with the neighboring S atom of the P═S group, resulting in the formation of an intramolecular N—H···S hydrogen bond (Fig. 1 and Table 2).

S2. Experimental

A suspension of (1) (2.5 mmol) and an equivalent amount of Lawesson's reagent in anhydrous xylene (50 ml) was refluxed with stirring under N₂ for 5 h. The reaction mixture was filtered and the filtrate concentrated on a rotatory evaporator at reduced pressure. The residue was chromatographed using a mixture of ethyl acetate and petroleum ether (1/5 v/v) as eluant, yielding a crude product. Further recrystallization of the crude product from a mixture of methylene chloride and light petroleum ether (1/3, v/v) afforded title compound, (2), as colorless crystals (m.p.: 373 K). ¹H NMR (CDCl₃ as a solvent, TMS as internal reference, δ, p.p.m.): 3.35 (d, 3H, 3J_H—H = 5.15 Hz, NHCH₃), 3.71–4.03 (m, 2H, NCH₂CH₂O), 3.91 (s, 3H, OCH₃), 4.32–4.65 (m, 2H, CH₂CH₂O), 7.03 (dd, 2H, 4J_P—H = 3.36 Hz, 3J_H—H = 8.50 Hz, H_arom), 7.06–7.85 (m, 4H, H_arom), 7.91 (dd, 2H, 3J_P—H = 8.12 Hz, 3J_H—H = 8.50 Hz, H_arom), 9.65 (br, 1H, NH). ³¹P NMR (CDCl₃ as a solvent, 85% H₃PO₄ as an external reference, δ, p.p.m.): 89.60. F T IR (KBr, cm⁻¹): 3234 (NH), 1595, 1568, 1502, 1452 (Ar), 1259 (C═S), 1113 (P–O–C), 1020 (Ar–O–C). Elemental analysis, found: C 53.62, H 4.89, N 7.78%; calculated: C 53.97, H 5.03, N 7.41%.

S3. Refinement

H atoms were located theoretically and refined with riding-model positional parameters and fixed isotropic displacement parameters. There are solvent accessible voids of 46 ų in the crystal.

Computing details

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

Figures

Fig. 1. View of the molecule of (2) with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. Dashed lines indicate the hydrogen-bonding interactions.

2-(p-Methoxyphenyl)-3-[o-(methylaminothiocarbonyl)phenyl]-1,3,2- oxazaphospholidine 2-sulfide

Crystal data

C17H19N2O2PS2	Dx = 1.321 Mg m^−3
Mr = 378.43	Melting point: 373 K
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 9.905 (3) Å	Cell parameters from 874 reflections
b = 19.091 (5) Å	θ = 2.4–22.1°
c = 20.384 (5) Å	µ = 0.38 mm^−1
β = 99.180 (5)°	T = 293 K
V = 3805.0 (17) Å^3	Prism, colorless
Z = 8	0.25 × 0.20 × 0.20 mm
F(000) = 1584

Data collection

Bruker SMART CCD area-detector diffractometer	10230 independent reflections
Radiation source: fine-focus sealed tube	6200 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ϕ and ω scans	θmax = 25.0°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→9
Tmin = 0.912, Tmax = 0.929	k = −16→22
15649 measured reflections	l = −24→24

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.04P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max = 0.028
10230 reflections	Δρmax = 0.28 e Å^−3
866 parameters	Δρmin = −0.24 e Å^−3
2 restraints	Absolute structure: Flack (1983), 3497 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (7)

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.

Least squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 0.1574 (0.0280) x + 5.6700 (0.0539) y + 19.2641 (0.0204) z = 4.4842 (0.0065)

* 0.0113 (0.0049) C1 * −0.0199 (0.0052) C2 * 0.0114 (0.0060) C3 * 0.0063 (0.0060) C4 * −0.0149 (0.0053) C5 * 0.0059 (0.0048) C6

Rms deviation of fitted atoms = 0.0126

2.8807 (0.0241) x + 17.9353 (0.0178) y − 4.5891 (0.0550) z = 4.9968 (0.0161)

Angle to previous plane (with approximate e.s.d.) = 84.17 (0.22)

* 0.0094 (0.0046) C11 * −0.0059 (0.0046) C12 * −0.0045 (0.0045) C13 * 0.0112 (0.0047) C14 * −0.0073 (0.0049) C15 * −0.0029 (0.0049) C16

Rms deviation of fitted atoms = 0.0074

8.3186 (0.0181) x − 2.8470 (0.0481) y + 7.7711 (0.0590) z = 3.3679 (0.0142)

Angle to previous plane (with approximate e.s.d.) = 89.45 (1/5)

* 0.0360 (0.0026) P1 * −0.1112 (0.0043) O1 * 0.1429 (0.0052) C10 * −0.1072 (0.0045) C9 * 0.0395 (0.0030) N1

Rms deviation of fitted atoms = 0.0971

− 0.1574 (0.0280) x + 5.6700 (0.0539) y + 19.2641 (0.0204) z = 4.4842 (0.0065)

Angle to previous plane (with approximate e.s.d.) = 63.85 (0.24)

* 0.0113 (0.0049) C1 * −0.0199 (0.0052) C2 * 0.0114 (0.0060) C3 * 0.0063 (0.0060) C4 * −0.0149 (0.0053) C5 * 0.0059 (0.0048) C6

Rms deviation of fitted atoms = 0.0126

− 0.8938 (0.0296) x − 6.1296 (0.0542) y + 19.2644 (0.0209) z = 5.8810 (0.0337)

Angle to previous plane (with approximate e.s.d.) = 36.28 (0.16)

* 0.0075 (0.0048) C18 * 0.0119 (0.0052) C19 * −0.0200 (0.0061) C20 * 0.0082 (0.0062) C21 * 0.0113 (0.0054) C22 * −0.0189 (0.0050) C23

Rms deviation of fitted atoms = 0.0138

2.8989 (0.0255) x + 17.3926 (0.0219) y + 4.8912 (0.0556) z = 14.0125 (0.0161)

Angle to previous plane (with approximate e.s.d.) = 87.41 (0.22)

* −0.0014 (0.0047) C28 * −0.0064 (0.0046) C29 * 0.0092 (0.0047) C30 * −0.0045 (0.0047) C31 * −0.0032 (0.0048) C32 * 0.0062 (0.0051) C33

Rms deviation of fitted atoms = 0.0057

− 8.1004 (0.0167) x + 3.2386 (0.0497) y + 13.7249 (0.0402) z = 0.6092 (0.0480)

Angle to previous plane (with approximate e.s.d.) = 85.71 (0.21)

* 0.1284 (0.0041) C26 * −0.1667 (0.0044) C27 * 0.1304 (0.0037) O3 * −0.0405 (0.0025) P2 * −0.0516 (0.0031) N4

Rms deviation of fitted atoms = 0.1145

− 0.8938 (0.0296) x − 6.1296 (0.0542) y + 19.2644 (0.0209) z = 5.8810 (0.0337)

Angle to previous plane (with approximate e.s.d.) = 57.47 (0.22)

* 0.0075 (0.0048) C18 * 0.0119 (0.0052) C19 * −0.0200 (0.0061) C20 * 0.0082 (0.0062) C21 * 0.0113 (0.0054) C22 * −0.0189 (0.0050) C23

Rms deviation of fitted atoms = 0.0138

− 0.8455 (0.0297) x + 6.4937 (0.0558) y + 19.1227 (0.0228) z = 7.6518 (0.0294)

Angle to previous plane (with approximate e.s.d.) = 38.62 (0.16)

* −0.0045 (0.0049) C35 * −0.0050 (0.0051) C36 * 0.0083 (0.0058) C37 * −0.0020 (0.0062) C38 * −0.0074 (0.0060) C39 * 0.0105 (0.0054) C40

Rms deviation of fitted atoms = 0.0069

− 3.0022 (0.0254) x + 17.4585 (0.0222) y − 4.4064 (0.0583) z = 11.9771 (0.0338)

Angle to previous plane (with approximate e.s.d.) = 85.07 (0.23)

* 0.0016 (0.0049) C45 * 0.0089 (0.0054) C46 * −0.0171 (0.0052) C47 * 0.0147 (0.0049) C48 * −0.0042 (0.0050) C49 * −0.0040 (0.0048) C50

Rms deviation of fitted atoms = 0.0102

8.0310 (0.0188) x + 3.1300 (0.0527) y − 13.9430 (0.0440) z = 1.4138 (0.0394)

Angle to previous plane (with approximate e.s.d.) = 86.86 (0.22)

* −0.0476 (0.0026) P3 * −0.0453 (0.0032) N6 * 0.1263 (0.0043) C43 * −0.1746 (0.0048) C44 * 0.1412 (0.0041) O5

Rms deviation of fitted atoms = 0.1189

− 0.8455 (0.0297) x + 6.4937 (0.0558) y + 19.1227 (0.0228) z = 7.6518 (0.0294)

Angle to previous plane (with approximate e.s.d.) = 57.34 (0.23)

* −0.0045 (0.0049) C35 * −0.0050 (0.0051) C36 * 0.0083 (0.0058) C37 * −0.0020 (0.0062) C38 * −0.0074 (0.0060) C39 * 0.0105 (0.0054) C40

Rms deviation of fitted atoms = 0.0069

− 0.0960 (0.0307) x − 6.0838 (0.0577) y + 19.1045 (0.0234) z = 3.2985 (0.0605)

Angle to previous plane (with approximate e.s.d.) = 38.74 (0.17)

* 0.0000 (0.0054) C52 * −0.0057 (0.0060) C53 * 0.0098 (0.0065) C54 * −0.0083 (0.0064) C55 * 0.0029 (0.0056) C56 * 0.0014 (0.0053) C57

Rms deviation of fitted atoms = 0.0059

− 2.8374 (0.0238) x + 17.8267 (0.0189) y + 5.2455 (0.0559) z = 18.3945 (0.0409)

Angle to previous plane (with approximate e.s.d.) = 84.74 (0.23)

* 0.0068 (0.0049) C62 * 0.0042 (0.0053) C63 * −0.0112 (0.0049) C64 * 0.0071 (0.0045) C65 * 0.0038 (0.0046) C66 * −0.0108 (0.0046) C67

Rms deviation of fitted atoms = 0.0079

8.3326 (0.0180) x + 2.8847 (0.0496) y + 7.7090 (0.0593) z = 13.1425 (0.0535)

Angle to previous plane (with approximate e.s.d.) = 89.35 (0.21)

* −0.0230 (0.0027) P4 * 0.0864 (0.0042) O7 * −0.1176 (0.0053) C61 * 0.0938 (0.0046) C60 * −0.0396 (0.0031) N8

Rms deviation of fitted atoms = 0.0802

− 0.0960 (0.0307) x − 6.0838 (0.0577) y + 19.1045 (0.0234) z = 3.2985 (0.0605)

Angle to previous plane (with approximate e.s.d.) = 64.17 (1/4)

* 0.0000 (0.0054) C52 * −0.0057 (0.0060) C53 * 0.0098 (0.0065) C54 * −0.0083 (0.0064) C55 * 0.0029 (0.0056) C56 * 0.0014 (0.0053) C57

Rms deviation of fitted atoms = 0.0059

Refinement. Most of the non-hydrogen atoms were located from an E-map, and the others were determined with successive difference Fourier syntheses. The structure was then refined by full-matrix least-squares method with anisotropic thermal parameters for all non-hydrogen atoms. A full-matrix least-squares refinement gave the final R1 = 0.0448 and wR₂ = 0.0861 with W = 1/[σ²(F_o²)+(0.0400P)²] and P = (F_o²+2Fc²)/3, S = 0.967. In the final difference Fourier map, the maximum and minimum peaks are 0.277 and −0.242 e Å⁻³, respectively. 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
P1	0.3111 (2)	0.28669 (9)	0.21001 (8)	0.0430 (4)
P2	0.91232 (18)	0.52552 (9)	0.45588 (8)	0.0421 (4)
P3	0.22228 (19)	0.77751 (9)	0.20459 (8)	0.0433 (4)
P4	0.80813 (19)	1.03120 (9)	0.44247 (8)	0.0444 (5)
S1	0.41810 (18)	0.29016 (9)	0.29825 (8)	0.0584 (5)
S2	0.6262 (2)	0.05347 (11)	0.15939 (10)	0.0809 (6)
S3	1.2587 (2)	0.28777 (11)	0.50442 (10)	0.0818 (6)
S4	0.95681 (18)	0.52990 (9)	0.36696 (8)	0.0576 (5)
S5	−0.1219 (2)	0.54058 (11)	0.15831 (10)	0.0797 (6)
S6	0.17872 (19)	0.78269 (10)	0.29344 (8)	0.0627 (5)
S7	0.4902 (2)	0.79975 (12)	0.49276 (11)	0.0886 (7)
S8	0.70860 (18)	1.03348 (10)	0.35285 (8)	0.0614 (5)
O1	0.3635 (4)	0.3366 (2)	0.1532 (2)	0.0539 (11)
O2	−0.2665 (5)	0.3730 (3)	0.1976 (2)	0.0626 (15)
O3	1.0048 (4)	0.5714 (2)	0.5121 (2)	0.0513 (12)
O4	0.3474 (5)	0.6129 (3)	0.4792 (3)	0.0715 (17)
O5	0.1303 (5)	0.8238 (2)	0.1485 (2)	0.0512 (12)
O6	0.7850 (5)	0.8670 (3)	0.1798 (3)	0.0749 (18)
O7	0.7526 (4)	1.0812 (2)	0.4979 (2)	0.0550 (12)
O8	1.3890 (6)	1.1148 (3)	0.4675 (3)	0.0621 (15)
N1	0.3236 (5)	0.2116 (2)	0.16960 (19)	0.0407 (12)
N2	0.5997 (5)	0.1613 (3)	0.2349 (2)	0.0525 (14)
H2B	0.5503	0.1859	0.2574	0.063*
N3	1.1860 (5)	0.4007 (3)	0.4339 (2)	0.0550 (14)
H3B	1.1228	0.4264	0.4122	0.066*
N4	0.9488 (4)	0.4496 (2)	0.4945 (2)	0.0381 (12)
N5	−0.0507 (5)	0.6535 (3)	0.2305 (2)	0.0538 (14)
H5B	0.0127	0.6786	0.2529	0.065*
N6	0.1858 (5)	0.7016 (2)	0.1664 (2)	0.0419 (12)
N7	0.5167 (6)	0.9089 (3)	0.4165 (2)	0.0584 (15)
H7A	0.5658	0.9332	0.3937	0.070*
N8	0.7939 (5)	0.9574 (2)	0.4833 (2)	0.0423 (12)
C1	0.2933 (8)	0.1429 (3)	0.1937 (3)	0.046 (2)
C2	0.1576 (7)	0.1245 (4)	0.1964 (3)	0.055 (2)
H2A	0.0880	0.1569	0.1841	0.066*
C3	0.1266 (11)	0.0584 (5)	0.2172 (4)	0.072 (3)
H3A	0.0368	0.0473	0.2210	0.086*
C4	0.2262 (10)	0.0098 (5)	0.2321 (4)	0.066 (2)
H4A	0.2043	−0.0348	0.2456	0.080*
C5	0.3595 (10)	0.0259 (4)	0.2273 (4)	0.064 (3)
H5A	0.4261	−0.0086	0.2365	0.077*
C6	0.3978 (8)	0.0926 (4)	0.2091 (3)	0.0439 (19)
C7	0.5429 (7)	0.1057 (3)	0.2024 (3)	0.0505 (17)
C8	0.7426 (7)	0.1835 (4)	0.2348 (4)	0.073 (2)
H8A	0.7614	0.2248	0.2616	0.109*
H8B	0.7558	0.1935	0.1901	0.109*
H8C	0.8035	0.1466	0.2527	0.109*
C9	0.3693 (6)	0.2205 (3)	0.1051 (3)	0.0537 (17)
H9A	0.2937	0.2144	0.0689	0.064*
H9B	0.4406	0.1871	0.0998	0.064*
C10	0.4229 (11)	0.2940 (4)	0.1068 (4)	0.090 (3)
H10A	0.5215	0.2933	0.1195	0.107*
H10B	0.4020	0.3144	0.0628	0.107*
C11	0.1370 (6)	0.3108 (3)	0.2096 (3)	0.0440 (16)
C12	0.0878 (6)	0.3321 (3)	0.2657 (3)	0.0463 (16)
H12A	0.1470	0.3323	0.3060	0.056*
C13	−0.0447 (7)	0.3533 (3)	0.2647 (3)	0.0515 (17)
H13A	−0.0753	0.3676	0.3034	0.062*
C14	−0.1309 (7)	0.3527 (3)	0.2049 (3)	0.0478 (17)
C15	−0.0873 (7)	0.3299 (4)	0.1475 (3)	0.0610 (19)
H15A	−0.1478	0.3286	0.1076	0.073*
C16	0.0455 (7)	0.3094 (4)	0.1496 (3)	0.0519 (19)
H16A	0.0754	0.2944	0.1110	0.062*
C17	−0.3118 (7)	0.4053 (4)	0.2527 (4)	0.076 (2)
H17A	−0.4068	0.4171	0.2414	0.114*
H17B	−0.2596	0.4471	0.2644	0.114*
H17C	−0.2996	0.3736	0.2897	0.114*
C18	0.9043 (7)	0.3816 (3)	0.4690 (3)	0.0404 (18)
C19	0.7668 (7)	0.3654 (4)	0.4578 (3)	0.049 (2)
H19A	0.7040	0.3989	0.4668	0.059*
C20	0.7205 (9)	0.3010 (4)	0.4334 (4)	0.070 (3)
H20A	0.6271	0.2919	0.4241	0.084*
C21	0.8115 (10)	0.2509 (4)	0.4232 (4)	0.069 (2)
H21A	0.7800	0.2068	0.4086	0.083*
C22	0.9504 (9)	0.2641 (4)	0.4340 (4)	0.059 (2)
H22A	1.0116	0.2290	0.4268	0.071*
C23	0.9992 (7)	0.3305 (4)	0.4558 (3)	0.0438 (19)
C24	1.1490 (6)	0.3430 (3)	0.4637 (3)	0.0453 (16)
C25	1.3266 (7)	0.4221 (4)	0.4362 (4)	0.078 (3)
H25A	1.3296	0.4647	0.4114	0.117*
H25B	1.3759	0.3861	0.4172	0.117*
H25C	1.3677	0.4298	0.4816	0.117*
C26	1.0391 (6)	0.4573 (3)	0.5591 (3)	0.0521 (17)
H26A	1.1098	0.4217	0.5645	0.063*
H26B	0.9872	0.4537	0.5955	0.063*
C27	1.0999 (8)	0.5289 (4)	0.5566 (4)	0.073 (2)
H27A	1.1154	0.5495	0.6006	0.088*
H27B	1.1868	0.5261	0.5406	0.088*
C28	0.7420 (6)	0.5525 (3)	0.4600 (3)	0.0414 (16)
C29	0.6579 (7)	0.5811 (3)	0.4073 (3)	0.0536 (18)
H29A	0.6906	0.5861	0.3673	0.064*
C30	0.5264 (7)	0.6029 (4)	0.4108 (4)	0.0599 (19)
H30A	0.4731	0.6233	0.3740	0.072*
C31	0.4746 (7)	0.5942 (4)	0.4697 (4)	0.0542 (18)
C32	0.5570 (7)	0.5653 (3)	0.5237 (3)	0.0584 (18)
H32A	0.5234	0.5595	0.5635	0.070*
C33	0.6879 (7)	0.5453 (4)	0.5195 (3)	0.051 (2)
H33A	0.7423	0.5264	0.5567	0.062*
C34	0.2619 (7)	0.6489 (4)	0.4260 (4)	0.086 (3)
H34A	0.1749	0.6588	0.4390	0.130*
H34B	0.2487	0.6198	0.3871	0.130*
H34C	0.3050	0.6919	0.4165	0.130*
C35	0.2311 (7)	0.6366 (4)	0.1940 (3)	0.0421 (18)
C36	0.3712 (8)	0.6222 (4)	0.2050 (4)	0.053 (2)
H36A	0.4333	0.6560	0.1958	0.063*
C37	0.4170 (8)	0.5574 (4)	0.2297 (4)	0.059 (2)
H37A	0.5103	0.5481	0.2379	0.071*
C38	0.3235 (10)	0.5052 (4)	0.2428 (4)	0.070 (3)
H38A	0.3546	0.4615	0.2588	0.084*
C39	0.1881 (9)	0.5199 (5)	0.2315 (4)	0.064 (2)
H39A	0.1264	0.4854	0.2397	0.077*
C40	0.1377 (8)	0.5858 (4)	0.2079 (4)	0.050 (2)
C41	−0.0133 (7)	0.5970 (3)	0.2007 (3)	0.0520 (17)
C42	−0.1910 (8)	0.6764 (4)	0.2282 (4)	0.076 (3)
H42A	−0.1925	0.7189	0.2533	0.114*
H42B	−0.2417	0.6408	0.2470	0.114*
H42C	−0.2317	0.6846	0.1829	0.114*
C43	0.0938 (7)	0.7091 (3)	0.1027 (3)	0.0586 (19)
H43A	0.0223	0.6738	0.0981	0.070*
H43B	0.1437	0.7053	0.0656	0.070*
C44	0.0349 (8)	0.7817 (4)	0.1067 (4)	0.075 (2)
H44A	0.0159	0.8022	0.0627	0.090*
H44B	−0.0501	0.7792	0.1245	0.090*
C45	0.3936 (7)	0.8042 (3)	0.1997 (3)	0.0448 (17)
C46	0.4434 (8)	0.7982 (4)	0.1404 (4)	0.062 (2)
H46A	0.3871	0.7805	0.1032	0.074*
C47	0.5743 (7)	0.8180 (4)	0.1355 (3)	0.0617 (19)
H47A	0.6076	0.8115	0.0958	0.074*
C48	0.6569 (7)	0.8476 (4)	0.1892 (4)	0.0553 (19)
C49	0.6096 (7)	0.8535 (4)	0.2492 (3)	0.0579 (18)
H49A	0.6659	0.8718	0.2862	0.070*
C50	0.4782 (7)	0.8321 (3)	0.2539 (3)	0.0557 (18)
H50A	0.4461	0.8366	0.2942	0.067*
C51	0.8719 (7)	0.9028 (4)	0.2317 (4)	0.096 (3)
H51A	0.9581	0.9127	0.2177	0.144*
H51B	0.8868	0.8739	0.2707	0.144*
H51C	0.8295	0.9459	0.2416	0.144*
C52	0.8248 (7)	0.8900 (4)	0.4602 (3)	0.0440 (18)
C53	0.9559 (9)	0.8739 (4)	0.4554 (4)	0.065 (2)
H53A	1.0222	0.9083	0.4659	0.077*
C54	0.9953 (10)	0.8106 (5)	0.4363 (5)	0.079 (3)
H54A	1.0869	0.8010	0.4349	0.095*
C55	0.8955 (13)	0.7601 (5)	0.4188 (4)	0.086 (3)
H55A	0.9200	0.7165	0.4040	0.103*
C56	0.7588 (9)	0.7739 (4)	0.4230 (4)	0.063 (2)
H56A	0.6925	0.7395	0.4122	0.075*
C57	0.7229 (8)	0.8407 (4)	0.4441 (3)	0.051 (2)
C58	0.5738 (7)	0.8537 (3)	0.4486 (3)	0.0505 (17)
C59	0.3796 (8)	0.9310 (4)	0.4170 (4)	0.079 (3)
H59A	0.3612	0.9722	0.3901	0.119*
H59B	0.3673	0.9413	0.4618	0.119*
H59C	0.3178	0.8944	0.3995	0.119*
C60	0.7474 (6)	0.9678 (3)	0.5470 (3)	0.0543 (17)
H60A	0.8221	0.9609	0.5834	0.065*
H60B	0.6744	0.9353	0.5520	0.065*
C61	0.6982 (11)	1.0401 (4)	0.5457 (4)	0.090 (3)
H61A	0.5991	1.0402	0.5354	0.108*
H61B	0.7240	1.0607	0.5894	0.108*
C62	0.9845 (6)	1.0572 (3)	0.4476 (3)	0.0437 (16)
C63	1.0700 (8)	1.0532 (4)	0.5071 (3)	0.059 (2)
H63A	1.0366	1.0373	0.5445	0.071*
C64	1.2049 (7)	1.0724 (3)	0.5120 (3)	0.0551 (18)
H64A	1.2622	1.0682	0.5526	0.066*
C65	1.2575 (7)	1.0978 (3)	0.4574 (3)	0.0460 (17)
C66	1.1707 (7)	1.1015 (3)	0.3971 (3)	0.0556 (18)
H66A	1.2033	1.1182	0.3597	0.067*
C67	1.0355 (7)	1.0807 (3)	0.3921 (3)	0.0519 (17)
H67A	0.9786	1.0824	0.3512	0.062*
C68	1.4435 (8)	1.1488 (4)	0.4155 (4)	0.079 (2)
H68A	1.5392	1.1577	0.4294	0.118*
H68B	1.3965	1.1924	0.4050	0.118*
H68C	1.4315	1.1194	0.3768	0.118*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0546 (12)	0.0347 (10)	0.0392 (9)	−0.0027 (8)	0.0057 (9)	−0.0004 (8)
P2	0.0459 (11)	0.0386 (10)	0.0419 (10)	0.0001 (8)	0.0071 (8)	−0.0040 (8)
P3	0.0483 (11)	0.0386 (10)	0.0432 (10)	−0.0007 (9)	0.0077 (9)	0.0031 (8)
P4	0.0554 (12)	0.0359 (11)	0.0412 (10)	0.0018 (8)	0.0057 (9)	0.0051 (8)
S1	0.0641 (12)	0.0594 (12)	0.0473 (10)	0.0034 (9)	−0.0042 (8)	−0.0111 (9)
S2	0.0843 (14)	0.0760 (15)	0.0811 (13)	0.0135 (11)	0.0091 (11)	−0.0238 (11)
S3	0.0695 (14)	0.0700 (14)	0.1001 (15)	0.0189 (11)	−0.0037 (11)	0.0071 (13)
S4	0.0690 (13)	0.0593 (12)	0.0478 (10)	0.0006 (9)	0.0191 (9)	0.0026 (9)
S5	0.0757 (14)	0.0620 (14)	0.0966 (15)	−0.0182 (11)	−0.0010 (11)	−0.0077 (12)
S6	0.0729 (13)	0.0681 (14)	0.0518 (11)	−0.0132 (10)	0.0245 (9)	−0.0133 (9)
S7	0.0843 (15)	0.0797 (16)	0.0996 (16)	−0.0200 (11)	0.0077 (12)	0.0261 (12)
S8	0.0705 (13)	0.0644 (13)	0.0451 (10)	−0.0029 (9)	−0.0036 (9)	0.0126 (9)
O1	0.061 (3)	0.044 (3)	0.056 (3)	0.006 (2)	0.007 (2)	−0.015 (2)
O2	0.054 (4)	0.065 (4)	0.068 (3)	0.001 (3)	0.009 (3)	0.004 (3)
O3	0.048 (3)	0.040 (3)	0.062 (3)	0.006 (2)	−0.004 (2)	−0.008 (2)
O4	0.041 (3)	0.075 (4)	0.099 (4)	0.011 (3)	0.015 (3)	0.012 (3)
O5	0.058 (3)	0.038 (3)	0.055 (3)	−0.001 (2)	0.003 (2)	0.005 (2)
O6	0.049 (4)	0.077 (4)	0.101 (4)	−0.006 (3)	0.020 (3)	−0.002 (3)
O7	0.060 (3)	0.043 (3)	0.063 (3)	0.001 (2)	0.013 (2)	0.011 (2)
O8	0.052 (4)	0.060 (3)	0.074 (3)	−0.005 (3)	0.011 (3)	0.006 (3)
N1	0.055 (3)	0.037 (3)	0.031 (3)	0.000 (2)	0.009 (2)	0.000 (2)
N2	0.046 (3)	0.046 (4)	0.064 (3)	0.000 (3)	0.005 (3)	0.005 (3)
N3	0.042 (3)	0.054 (4)	0.070 (4)	0.002 (3)	0.010 (3)	−0.010 (3)
N4	0.044 (3)	0.032 (3)	0.037 (3)	−0.004 (2)	0.003 (2)	−0.001 (2)
N5	0.051 (4)	0.048 (4)	0.066 (4)	−0.007 (3)	0.019 (3)	0.001 (3)
N6	0.051 (3)	0.031 (3)	0.043 (3)	−0.003 (2)	0.006 (2)	0.003 (2)
N7	0.070 (4)	0.049 (4)	0.053 (3)	0.000 (3)	0.000 (3)	0.004 (3)
N8	0.061 (3)	0.030 (3)	0.037 (3)	0.002 (2)	0.011 (2)	0.001 (2)
C1	0.086 (6)	0.026 (4)	0.027 (3)	−0.005 (4)	0.008 (4)	−0.004 (3)
C2	0.051 (5)	0.054 (5)	0.061 (4)	−0.006 (4)	0.014 (4)	−0.010 (4)
C3	0.097 (7)	0.048 (6)	0.077 (6)	−0.029 (5)	0.033 (5)	−0.004 (5)
C4	0.077 (7)	0.049 (5)	0.075 (5)	−0.022 (5)	0.015 (5)	0.001 (4)
C5	0.098 (8)	0.037 (5)	0.050 (4)	0.000 (4)	−0.013 (5)	0.004 (4)
C6	0.051 (5)	0.047 (5)	0.032 (4)	−0.003 (4)	0.002 (3)	−0.007 (3)
C7	0.067 (5)	0.034 (4)	0.046 (4)	0.011 (3)	−0.007 (3)	−0.004 (3)
C8	0.073 (6)	0.056 (5)	0.089 (6)	0.003 (4)	0.012 (5)	0.005 (4)
C9	0.075 (5)	0.044 (4)	0.042 (4)	0.000 (3)	0.010 (3)	0.002 (3)
C10	0.154 (9)	0.053 (6)	0.072 (6)	−0.020 (5)	0.049 (6)	0.003 (5)
C11	0.050 (4)	0.041 (4)	0.039 (4)	0.004 (3)	0.002 (3)	−0.001 (3)
C12	0.050 (4)	0.053 (4)	0.033 (3)	−0.004 (3)	−0.004 (3)	−0.001 (3)
C13	0.047 (4)	0.061 (5)	0.048 (4)	0.003 (3)	0.014 (3)	−0.011 (3)
C14	0.041 (4)	0.041 (4)	0.061 (5)	−0.006 (3)	0.004 (4)	0.003 (3)
C15	0.058 (5)	0.077 (5)	0.044 (4)	0.005 (4)	−0.003 (3)	0.007 (4)
C16	0.058 (5)	0.056 (5)	0.040 (4)	0.006 (4)	0.001 (4)	0.001 (3)
C17	0.051 (5)	0.084 (6)	0.098 (6)	0.005 (4)	0.021 (4)	−0.006 (5)
C18	0.051 (5)	0.034 (4)	0.035 (4)	−0.003 (4)	0.004 (3)	0.003 (3)
C19	0.044 (5)	0.048 (5)	0.055 (4)	−0.001 (4)	0.005 (3)	0.006 (4)
C20	0.073 (6)	0.055 (6)	0.077 (6)	−0.030 (5)	−0.005 (5)	0.007 (5)
C21	0.085 (7)	0.042 (5)	0.079 (5)	−0.011 (5)	0.008 (5)	−0.007 (4)
C22	0.070 (6)	0.031 (4)	0.076 (5)	−0.008 (4)	0.011 (4)	−0.008 (4)
C23	0.055 (5)	0.033 (4)	0.042 (4)	0.002 (3)	0.002 (3)	−0.009 (3)
C24	0.055 (4)	0.035 (4)	0.046 (4)	0.003 (3)	0.008 (3)	−0.013 (3)
C25	0.057 (6)	0.079 (6)	0.104 (6)	−0.008 (4)	0.030 (5)	−0.013 (5)
C26	0.057 (4)	0.057 (5)	0.041 (3)	−0.006 (3)	0.003 (3)	−0.008 (3)
C27	0.080 (6)	0.067 (6)	0.064 (5)	−0.008 (4)	−0.014 (4)	−0.014 (4)
C28	0.042 (4)	0.039 (4)	0.041 (4)	0.001 (3)	−0.002 (3)	0.002 (3)
C29	0.058 (5)	0.058 (5)	0.045 (4)	−0.005 (4)	0.010 (3)	0.003 (3)
C30	0.052 (5)	0.052 (5)	0.073 (5)	0.003 (4)	0.000 (4)	0.009 (4)
C31	0.042 (5)	0.049 (5)	0.070 (5)	0.000 (3)	0.003 (4)	−0.002 (4)
C32	0.053 (5)	0.063 (5)	0.062 (5)	0.009 (4)	0.018 (4)	−0.002 (4)
C33	0.053 (5)	0.061 (5)	0.039 (4)	0.012 (4)	0.004 (3)	0.003 (3)
C34	0.052 (5)	0.087 (6)	0.116 (7)	0.003 (4)	0.000 (5)	0.014 (6)
C35	0.054 (5)	0.041 (4)	0.033 (4)	−0.006 (4)	0.012 (3)	−0.003 (3)
C36	0.042 (5)	0.048 (5)	0.070 (5)	0.002 (4)	0.012 (4)	0.003 (4)
C37	0.051 (5)	0.060 (6)	0.068 (5)	0.005 (4)	0.011 (4)	0.004 (4)
C38	0.088 (7)	0.044 (5)	0.076 (5)	0.019 (5)	0.008 (5)	0.011 (4)
C39	0.060 (6)	0.058 (6)	0.076 (5)	−0.009 (4)	0.020 (4)	0.004 (4)
C40	0.053 (5)	0.041 (5)	0.053 (4)	0.003 (4)	0.001 (4)	−0.009 (4)
C41	0.056 (5)	0.048 (4)	0.053 (4)	−0.008 (3)	0.013 (3)	0.011 (3)
C42	0.050 (5)	0.070 (5)	0.112 (7)	0.003 (4)	0.024 (5)	0.008 (5)
C43	0.075 (5)	0.061 (5)	0.036 (3)	−0.011 (4)	−0.002 (3)	0.005 (3)
C44	0.079 (6)	0.054 (5)	0.081 (5)	0.007 (4)	−0.023 (5)	0.008 (4)
C45	0.049 (4)	0.040 (4)	0.044 (4)	−0.002 (3)	0.005 (4)	0.000 (3)
C46	0.046 (5)	0.074 (6)	0.064 (6)	−0.015 (4)	0.003 (4)	−0.002 (4)
C47	0.070 (5)	0.071 (5)	0.049 (4)	−0.006 (4)	0.024 (4)	0.001 (4)
C48	0.048 (5)	0.047 (4)	0.072 (5)	−0.004 (3)	0.014 (4)	0.004 (4)
C49	0.052 (5)	0.063 (5)	0.057 (5)	−0.009 (4)	0.001 (4)	−0.017 (4)
C50	0.063 (5)	0.054 (5)	0.053 (4)	−0.005 (4)	0.020 (4)	−0.012 (3)
C51	0.046 (5)	0.080 (6)	0.158 (8)	−0.013 (4)	0.005 (5)	−0.021 (6)
C52	0.044 (5)	0.042 (4)	0.047 (4)	0.006 (4)	0.010 (3)	0.001 (3)
C53	0.089 (7)	0.037 (5)	0.075 (5)	0.019 (4)	0.035 (4)	0.012 (4)
C54	0.072 (6)	0.076 (7)	0.097 (7)	0.008 (6)	0.036 (5)	0.018 (6)
C55	0.144 (10)	0.052 (6)	0.069 (6)	0.044 (7)	0.039 (6)	0.009 (5)
C56	0.092 (7)	0.032 (5)	0.062 (5)	0.003 (4)	0.007 (4)	−0.007 (4)
C57	0.074 (6)	0.042 (5)	0.034 (4)	0.011 (4)	0.004 (4)	−0.004 (3)
C58	0.063 (5)	0.040 (4)	0.044 (4)	−0.005 (3)	−0.005 (3)	−0.004 (3)
C59	0.053 (6)	0.080 (6)	0.101 (6)	0.014 (4)	0.002 (5)	−0.012 (5)
C60	0.079 (5)	0.046 (4)	0.040 (3)	−0.008 (3)	0.015 (3)	0.001 (3)
C61	0.150 (9)	0.054 (6)	0.077 (6)	0.032 (5)	0.055 (6)	0.008 (5)
C62	0.053 (4)	0.034 (4)	0.044 (4)	−0.002 (3)	0.007 (3)	0.014 (3)
C63	0.057 (5)	0.075 (6)	0.045 (4)	−0.008 (4)	0.010 (4)	0.011 (4)
C64	0.065 (5)	0.060 (5)	0.038 (4)	0.002 (4)	0.003 (3)	0.009 (3)
C65	0.058 (5)	0.030 (4)	0.051 (4)	0.003 (3)	0.011 (4)	−0.004 (3)
C66	0.069 (5)	0.054 (5)	0.048 (4)	0.003 (4)	0.022 (4)	0.007 (3)
C67	0.058 (5)	0.048 (4)	0.048 (4)	0.005 (3)	0.001 (3)	0.008 (3)
C68	0.073 (5)	0.065 (5)	0.104 (6)	−0.007 (4)	0.029 (4)	0.007 (5)

Geometric parameters (Å, º)

P1—O1	1.646 (5)	C21—C22	1.381 (10)
P1—N1	1.668 (5)	C21—H21A	0.9300
P1—C11	1.784 (6)	C22—C23	1.404 (10)
P1—S1	1.938 (2)	C22—H22A	0.9300
P2—O3	1.608 (4)	C23—C24	1.486 (9)
P2—N4	1.662 (5)	C25—H25A	0.9600
P2—C28	1.779 (6)	C25—H25B	0.9600
P2—S4	1.934 (2)	C25—H25C	0.9600
P3—O5	1.609 (4)	C26—C27	1.498 (9)
P3—N6	1.657 (5)	C26—H26A	0.9700
P3—C45	1.790 (7)	C26—H26B	0.9700
P3—S6	1.930 (3)	C27—H27A	0.9700
P4—O7	1.640 (5)	C27—H27B	0.9700
P4—N8	1.653 (5)	C28—C29	1.363 (8)
P4—C62	1.804 (6)	C28—C33	1.409 (9)
P4—S8	1.933 (2)	C29—C30	1.380 (9)
S2—C7	1.635 (6)	C29—H29A	0.9300
S3—C24	1.641 (6)	C30—C31	1.389 (9)
S5—C41	1.663 (7)	C30—H30A	0.9300
S7—C58	1.672 (7)	C31—C32	1.378 (9)
O1—C10	1.442 (9)	C32—C33	1.367 (9)
O2—C14	1.383 (8)	C32—H32A	0.9300
O2—C17	1.415 (9)	C33—H33A	0.9300
O3—C27	1.448 (7)	C34—H34A	0.9600
O4—C31	1.353 (8)	C34—H34B	0.9600
O4—C34	1.439 (8)	C34—H34C	0.9600
O5—C44	1.417 (7)	C35—C36	1.397 (9)
O6—C48	1.365 (8)	C35—C40	1.401 (10)
O6—C51	1.428 (9)	C36—C37	1.385 (10)
O7—C61	1.423 (9)	C36—H36A	0.9300
O8—C65	1.327 (8)	C37—C38	1.414 (11)
O8—C68	1.421 (9)	C37—H37A	0.9300
N1—C1	1.449 (8)	C38—C39	1.354 (11)
N1—C9	1.467 (7)	C38—H38A	0.9300
N2—C7	1.327 (7)	C39—C40	1.410 (10)
N2—C8	1.478 (8)	C39—H39A	0.9300
N2—H2B	0.8600	C40—C41	1.494 (10)
N3—C24	1.338 (7)	C42—H42A	0.9600
N3—C25	1.445 (8)	C42—H42B	0.9600
N3—H3B	0.8600	C42—H42C	0.9600
N4—C18	1.441 (8)	C43—C44	1.511 (8)
N4—C26	1.475 (6)	C43—H43A	0.9700
N5—C41	1.320 (8)	C43—H43B	0.9700
N5—C42	1.451 (8)	C44—H44A	0.9700
N5—H5B	0.8600	C44—H44B	0.9700
N6—C35	1.407 (8)	C45—C46	1.382 (10)
N6—C43	1.469 (6)	C45—C50	1.382 (8)
N7—C58	1.318 (7)	C46—C47	1.369 (10)
N7—C59	1.424 (8)	C46—H46A	0.9300
N7—H7A	0.8600	C47—C48	1.378 (9)
N8—C52	1.420 (8)	C47—H47A	0.9300
N8—C60	1.458 (7)	C48—C49	1.383 (9)
C1—C2	1.399 (9)	C49—C50	1.383 (9)
C1—C6	1.409 (10)	C49—H49A	0.9300
C2—C3	1.382 (10)	C50—H50A	0.9300
C2—H2A	0.9300	C51—H51A	0.9600
C3—C4	1.354 (12)	C51—H51B	0.9600
C3—H3A	0.9300	C51—H51C	0.9600
C4—C5	1.374 (11)	C52—C53	1.353 (9)
C4—H4A	0.9300	C52—C57	1.382 (10)
C5—C6	1.395 (10)	C53—C54	1.347 (11)
C5—H5A	0.9300	C53—H53A	0.9300
C6—C7	1.487 (9)	C54—C55	1.386 (13)
C8—H8A	0.9600	C54—H54A	0.9300
C8—H8B	0.9600	C55—C56	1.396 (12)
C8—H8C	0.9600	C55—H55A	0.9300
C9—C10	1.500 (9)	C56—C57	1.409 (10)
C9—H9A	0.9700	C56—H56A	0.9300
C9—H9B	0.9700	C57—C58	1.516 (10)
C10—H10A	0.9700	C59—H59A	0.9600
C10—H10B	0.9700	C59—H59B	0.9600
C11—C12	1.373 (8)	C59—H59C	0.9600
C11—C16	1.402 (8)	C60—C61	1.461 (9)
C12—C13	1.370 (8)	C60—H60A	0.9700
C12—H12A	0.9300	C60—H60B	0.9700
C13—C14	1.372 (9)	C61—H61A	0.9700
C13—H13A	0.9300	C61—H61B	0.9700
C14—C15	1.382 (9)	C62—C63	1.366 (8)
C15—C16	1.366 (9)	C62—C67	1.384 (8)
C15—H15A	0.9300	C63—C64	1.374 (9)
C16—H16A	0.9300	C63—H63A	0.9300
C17—H17A	0.9600	C64—C65	1.389 (9)
C17—H17B	0.9600	C64—H64A	0.9300
C17—H17C	0.9600	C65—C66	1.385 (8)
C18—C19	1.379 (9)	C66—C67	1.385 (9)
C18—C23	1.409 (10)	C66—H66A	0.9300
C19—C20	1.378 (10)	C67—H67A	0.9300
C19—H19A	0.9300	C68—H68A	0.9600
C20—C21	1.353 (11)	C68—H68B	0.9600
C20—H20A	0.9300	C68—H68C	0.9600
O1—P1—N1	95.4 (2)	C26—C27—H27A	110.1
O1—P1—C11	105.1 (3)	O3—C27—H27B	110.1
N1—P1—C11	111.5 (3)	C26—C27—H27B	110.1
O1—P1—S1	116.48 (18)	H27A—C27—H27B	108.4
N1—P1—S1	114.54 (18)	C29—C28—C33	116.7 (6)
C11—P1—S1	112.3 (2)	C29—C28—P2	122.9 (5)
O3—P2—N4	94.7 (2)	C33—C28—P2	120.4 (5)
O3—P2—C28	104.2 (3)	C28—C29—C30	122.9 (7)
N4—P2—C28	111.5 (3)	C28—C29—H29A	118.5
O3—P2—S4	117.1 (2)	C30—C29—H29A	118.5
N4—P2—S4	114.65 (18)	C29—C30—C31	119.3 (6)
C28—P2—S4	113.0 (2)	C29—C30—H30A	120.3
O5—P3—N6	95.2 (2)	C31—C30—H30A	120.3
O5—P3—C45	103.8 (3)	O4—C31—C32	115.9 (7)
N6—P3—C45	111.1 (3)	O4—C31—C30	125.0 (7)
O5—P3—S6	116.9 (2)	C32—C31—C30	119.1 (7)
N6—P3—S6	114.91 (19)	C33—C32—C31	120.6 (7)
C45—P3—S6	113.2 (2)	C33—C32—H32A	119.7
O7—P4—N8	94.8 (2)	C31—C32—H32A	119.7
O7—P4—C62	103.2 (3)	C32—C33—C28	121.4 (6)
N8—P4—C62	111.4 (3)	C32—C33—H33A	119.3
O7—P4—S8	117.52 (19)	C28—C33—H33A	119.3
N8—P4—S8	115.05 (18)	O4—C34—H34A	109.5
C62—P4—S8	113.1 (2)	O4—C34—H34B	109.5
C10—O1—P1	110.1 (4)	H34A—C34—H34B	109.5
C14—O2—C17	117.5 (5)	O4—C34—H34C	109.5
C27—O3—P2	112.3 (4)	H34A—C34—H34C	109.5
C31—O4—C34	117.9 (6)	H34B—C34—H34C	109.5
C44—O5—P3	111.2 (4)	C36—C35—C40	120.2 (7)
C48—O6—C51	119.3 (6)	C36—C35—N6	118.9 (6)
C61—O7—P4	110.9 (4)	C40—C35—N6	120.9 (6)
C65—O8—C68	118.4 (6)	C37—C36—C35	119.5 (7)
C1—N1—C9	121.2 (5)	C37—C36—H36A	120.2
C1—N1—P1	125.1 (4)	C35—C36—H36A	120.2
C9—N1—P1	113.7 (4)	C36—C37—C38	120.8 (7)
C7—N2—C8	123.9 (6)	C36—C37—H37A	119.6
C7—N2—H2B	118.0	C38—C37—H37A	119.6
C8—N2—H2B	118.0	C39—C38—C37	118.9 (8)
C24—N3—C25	123.5 (6)	C39—C38—H38A	120.6
C24—N3—H3B	118.3	C37—C38—H38A	120.6
C25—N3—H3B	118.3	C38—C39—C40	122.0 (8)
C18—N4—C26	121.2 (5)	C38—C39—H39A	119.0
C18—N4—P2	125.7 (4)	C40—C39—H39A	119.0
C26—N4—P2	113.0 (4)	C35—C40—C39	118.6 (7)
C41—N5—C42	124.7 (6)	C35—C40—C41	124.3 (7)
C41—N5—H5B	117.6	C39—C40—C41	117.1 (7)
C42—N5—H5B	117.6	N5—C41—C40	114.9 (6)
C35—N6—C43	123.5 (5)	N5—C41—S5	124.2 (5)
C35—N6—P3	123.5 (4)	C40—C41—S5	120.8 (5)
C43—N6—P3	112.9 (4)	N5—C42—H42A	109.5
C58—N7—C59	124.5 (6)	N5—C42—H42B	109.5
C58—N7—H7A	117.7	H42A—C42—H42B	109.5
C59—N7—H7A	117.7	N5—C42—H42C	109.5
C52—N8—C60	122.2 (5)	H42A—C42—H42C	109.5
C52—N8—P4	124.4 (4)	H42B—C42—H42C	109.5
C60—N8—P4	113.4 (4)	N6—C43—C44	103.4 (5)
C2—C1—C6	119.8 (7)	N6—C43—H43A	111.1
C2—C1—N1	119.4 (7)	C44—C43—H43A	111.1
C6—C1—N1	120.5 (7)	N6—C43—H43B	111.1
C3—C2—C1	120.2 (8)	C44—C43—H43B	111.1
C3—C2—H2A	119.9	H43A—C43—H43B	109.1
C1—C2—H2A	119.9	O5—C44—C43	109.1 (5)
C4—C3—C2	120.4 (9)	O5—C44—H44A	109.9
C4—C3—H3A	119.8	C43—C44—H44A	109.9
C2—C3—H3A	119.8	O5—C44—H44B	109.9
C3—C4—C5	120.3 (8)	C43—C44—H44B	109.9
C3—C4—H4A	119.9	H44A—C44—H44B	108.3
C5—C4—H4A	119.9	C46—C45—C50	118.5 (7)
C4—C5—C6	121.9 (8)	C46—C45—P3	119.9 (5)
C4—C5—H5A	119.0	C50—C45—P3	121.6 (5)
C6—C5—H5A	119.0	C47—C46—C45	120.9 (7)
C5—C6—C1	117.3 (7)	C47—C46—H46A	119.5
C5—C6—C7	119.1 (7)	C45—C46—H46A	119.5
C1—C6—C7	123.4 (7)	C46—C47—C48	120.3 (7)
N2—C7—C6	115.3 (6)	C46—C47—H47A	119.8
N2—C7—S2	123.1 (6)	C48—C47—H47A	119.8
C6—C7—S2	121.6 (5)	O6—C48—C47	116.5 (7)
N2—C8—H8A	109.5	O6—C48—C49	123.8 (7)
N2—C8—H8B	109.5	C47—C48—C49	119.6 (7)
H8A—C8—H8B	109.5	C48—C49—C50	119.5 (6)
N2—C8—H8C	109.5	C48—C49—H49A	120.3
H8A—C8—H8C	109.5	C50—C49—H49A	120.3
H8B—C8—H8C	109.5	C45—C50—C49	121.0 (6)
N1—C9—C10	104.2 (5)	C45—C50—H50A	119.5
N1—C9—H9A	110.9	C49—C50—H50A	119.5
C10—C9—H9A	110.9	O6—C51—H51A	109.5
N1—C9—H9B	110.9	O6—C51—H51B	109.5
C10—C9—H9B	110.9	H51A—C51—H51B	109.5
H9A—C9—H9B	108.9	O6—C51—H51C	109.5
O1—C10—C9	111.3 (7)	H51A—C51—H51C	109.5
O1—C10—H10A	109.4	H51B—C51—H51C	109.5
C9—C10—H10A	109.4	C53—C52—C57	120.0 (7)
O1—C10—H10B	109.4	C53—C52—N8	119.4 (7)
C9—C10—H10B	109.4	C57—C52—N8	120.6 (7)
H10A—C10—H10B	108.0	C54—C53—C52	123.5 (9)
C12—C11—C16	117.7 (6)	C54—C53—H53A	118.3
C12—C11—P1	123.0 (4)	C52—C53—H53A	118.3
C16—C11—P1	119.3 (5)	C53—C54—C55	118.1 (9)
C13—C12—C11	122.8 (5)	C53—C54—H54A	121.0
C13—C12—H12A	118.6	C55—C54—H54A	121.0
C11—C12—H12A	118.6	C54—C55—C56	120.8 (9)
C12—C13—C14	118.0 (6)	C54—C55—H55A	119.6
C12—C13—H13A	121.0	C56—C55—H55A	119.6
C14—C13—H13A	121.0	C55—C56—C57	118.9 (8)
C13—C14—C15	121.4 (6)	C55—C56—H56A	120.5
C13—C14—O2	123.4 (6)	C57—C56—H56A	120.5
C15—C14—O2	115.2 (6)	C52—C57—C56	118.7 (8)
C16—C15—C14	119.5 (6)	C52—C57—C58	123.7 (7)
C16—C15—H15A	120.3	C56—C57—C58	117.6 (7)
C14—C15—H15A	120.3	N7—C58—C57	116.5 (6)
C15—C16—C11	120.6 (6)	N7—C58—S7	123.4 (6)
C15—C16—H16A	119.7	C57—C58—S7	120.2 (5)
C11—C16—H16A	119.7	N7—C59—H59A	109.5
O2—C17—H17A	109.5	N7—C59—H59B	109.5
O2—C17—H17B	109.5	H59A—C59—H59B	109.5
H17A—C17—H17B	109.5	N7—C59—H59C	109.5
O2—C17—H17C	109.5	H59A—C59—H59C	109.5
H17A—C17—H17C	109.5	H59B—C59—H59C	109.5
H17B—C17—H17C	109.5	N8—C60—C61	105.4 (6)
C19—C18—C23	119.0 (7)	N8—C60—H60A	110.7
C19—C18—N4	119.9 (6)	C61—C60—H60A	110.7
C23—C18—N4	121.1 (6)	N8—C60—H60B	110.7
C20—C19—C18	121.5 (8)	C61—C60—H60B	110.7
C20—C19—H19A	119.2	H60A—C60—H60B	108.8
C18—C19—H19A	119.2	O7—C61—C60	111.7 (7)
C21—C20—C19	119.7 (8)	O7—C61—H61A	109.3
C21—C20—H20A	120.2	C60—C61—H61A	109.3
C19—C20—H20A	120.2	O7—C61—H61B	109.3
C20—C21—C22	121.2 (8)	C60—C61—H61B	109.3
C20—C21—H21A	119.4	H61A—C61—H61B	107.9
C22—C21—H21A	119.4	C63—C62—C67	119.2 (6)
C21—C22—C23	119.9 (8)	C63—C62—P4	119.5 (5)
C21—C22—H22A	120.0	C67—C62—P4	121.2 (5)
C23—C22—H22A	120.0	C62—C63—C64	120.5 (7)
C22—C23—C18	118.6 (7)	C62—C63—H63A	119.8
C22—C23—C24	117.8 (7)	C64—C63—H63A	119.8
C18—C23—C24	123.6 (6)	C63—C64—C65	121.3 (6)
N3—C24—C23	115.1 (5)	C63—C64—H64A	119.3
N3—C24—S3	123.5 (5)	C65—C64—H64A	119.3
C23—C24—S3	121.4 (5)	O8—C65—C66	125.5 (6)
N3—C25—H25A	109.5	O8—C65—C64	116.5 (6)
N3—C25—H25B	109.5	C66—C65—C64	118.0 (7)
H25A—C25—H25B	109.5	C65—C66—C67	120.4 (6)
N3—C25—H25C	109.5	C65—C66—H66A	119.8
H25A—C25—H25C	109.5	C67—C66—H66A	119.8
H25B—C25—H25C	109.5	C62—C67—C66	120.5 (6)
N4—C26—C27	104.5 (5)	C62—C67—H67A	119.8
N4—C26—H26A	110.9	C66—C67—H67A	119.8
C27—C26—H26A	110.9	O8—C68—H68A	109.5
N4—C26—H26B	110.9	O8—C68—H68B	109.5
C27—C26—H26B	110.9	H68A—C68—H68B	109.5
H26A—C26—H26B	108.9	O8—C68—H68C	109.5
O3—C27—C26	108.0 (5)	H68A—C68—H68C	109.5
O3—C27—H27A	110.1	H68B—C68—H68C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···S1	0.86	2.59	3.420 (6)	162
N3—H3B···S4	0.86	2.64	3.480 (6)	165
N5—H5B···S6	0.86	2.63	3.458 (5)	163
N7—H7A···S8	0.86	2.60	3.426 (6)	163