(4R,5R)-2-(N-Methyl-benzyl­amino)-3-nitro-4-(1′,2′,3′,4′,5′-penta-O-acetyl-D-manno-pentitol-1-yl)-5-phenyl-5-phenyl­carbamoyl-4,5-di­hydro­thio­phene at 150 K

The crystal structure of the title compound, C₄₀H₄₃N₃O₁₃S, has been determined at room temperature and at 150 K. From the cyclo­addition of thio­isomünchnones with chiral nitro­alkenes, two diastereomeric di­hydro­thio­phenes were obtained, showing that regiospecificity and facial selectivity were involved in these cyclo­additions reactions where only one of the two diastereomeric di­hydro­thio­phenes could be isolated in the solid state. The chiralities of the two new centres at C4 and C5, determined with respect to that known at C6 are R,R. N—H...O hydrogen bonds join the mol­ecules in chains running along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.041
• wR factor = 0.108
• Data-to-parameter ratio = 9.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



DIFF_012  Alert A _diffrn_reflns_av_R_equivalents is missing
          R factor for symmetry-equivalent intensities.
          The following tests will not be performed
          RINTA

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.98
         From the CIF: _reflns_number_total               5019
         Count of symmetry unique reflns         5025
         Completeness (_total/calc)             99.88%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure


 1 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 0 Alert Level C = Please check

---

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 (de Boer & Duissenberg, 1984) and CELDIM (in CAD4; Retting, 1989); data reduction: XRAY76 System (Stewart et al., 1976); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL93.

(4R,5R)-2-(N-Methyl-benzylamino)-3-nitro-4-(1',2',3',4',5'-penta-O-acetyl-D– manno-pentitol-1-yl)-5-phenyl-5-phenylcarbamoyl-4,5-dihydrothiophene

Crystal data

C40H43N3O13S	Dx = 1.352 Mg m^−3
Mr = 805.83	Melting point = 458–460 K
Monoclinic, P21	Mo Kα radiation, λ = 0.71069 Å
a = 15.575 (3) Å	Cell parameters from 25 reflections
b = 10.434 (8) Å	θ = 6–10°
c = 12.217 (3) Å	µ = 0.15 mm^−1
β = 94.65 (1)°	T = 150 K
V = 1978.8 (16) Å^3	Prism, yellow
Z = 2	0.40 × 0.28 × 0.24 mm
F(000) = 848

Data collection

Enraf-Nonius CAD-4 diffractometer	θmax = 28.0°, θmin = 2.0°
Radiation source: fine-focus sealed tube	h = 0→20
Graphite monochromator	k = 0→13
ω–2θ scans	l = −16→16
5025 measured reflections	3 standard reflections every 120 min
5019 independent reflections	intensity decay: none
4290 reflections with I > 2σ(I)

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)] = 0.041	H-atom parameters not refined
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0726P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.029
5019 reflections	Δρmax = 0.29 e Å^−3
514 parameters	Δρmin = −0.68 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (8)

Special details

Experimental. Scattering factors, dispersion correction coefficients were taken from International Tables for Crystallography, Vol. C. (1992), Tables 6.1.1.4, 4.2.6.8 and 4.2.4.2 respectively.

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. Weighted R-factorswR and all goodnesses of fit S are based on F², conventional R-factors Rare based on F, with F set to zero for negative F².R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.30713 (4)	0.77887 (7)	0.12579 (5)	0.01730 (14)
O31	0.49969 (12)	0.6455 (2)	−0.1003 (2)	0.0250 (5)
O32	0.39217 (13)	0.6302 (3)	−0.2249 (2)	0.0326 (6)
O51	0.25605 (15)	0.4491 (2)	−0.0084 (2)	0.0274 (5)
O61	0.26670 (11)	0.9161 (2)	−0.1526 (2)	0.0164 (4)
O62	0.17390 (14)	1.0012 (2)	−0.0413 (2)	0.0293 (5)
O71	0.16672 (12)	0.6316 (2)	−0.2733 (2)	0.0187 (4)
O72	0.25226 (14)	0.5359 (2)	−0.3905 (2)	0.0283 (5)
O81	0.07989 (12)	0.8659 (2)	−0.3229 (2)	0.0188 (4)
O82	0.10603 (15)	1.0781 (2)	−0.2992 (2)	0.0315 (5)
O91	0.25101 (12)	0.7988 (2)	−0.49573 (15)	0.0215 (4)
O92	0.2314 (2)	0.6547 (3)	−0.6322 (2)	0.0358 (6)
O101	0.13341 (14)	1.0004 (2)	−0.5583 (2)	0.0298 (5)
O102	−0.0022 (2)	1.0695 (3)	−0.5446 (2)	0.0522 (8)
N2	0.46770 (15)	0.8268 (2)	0.0760 (2)	0.0204 (5)
N3	0.42282 (15)	0.6644 (3)	−0.1318 (2)	0.0209 (5)
N5	0.2637 (2)	0.4991 (2)	0.1722 (2)	0.0213 (5)
H5	0.2593	0.5609	0.2205	0.026*
C2	0.39286 (15)	0.7722 (3)	0.0398 (2)	0.0164 (5)
C3	0.3662 (2)	0.7177 (3)	−0.0606 (2)	0.0167 (5)
C4	0.2708 (2)	0.6943 (3)	−0.0823 (2)	0.0145 (5)
H4	0.2639	0.6106	−0.1219	0.017*
C5	0.2389 (2)	0.6737 (3)	0.0347 (2)	0.0153 (5)
C6	0.22137 (15)	0.7962 (3)	−0.1552 (2)	0.0136 (5)
H6	0.1626	0.8091	−0.1295	0.016*
C7	0.2134 (2)	0.7515 (3)	−0.2760 (2)	0.0157 (5)
H7	0.2722	0.7350	−0.3004	0.019*
C8	0.1662 (2)	0.8458 (3)	−0.3542 (2)	0.0170 (5)
H8	0.1977	0.9293	−0.3508	0.020*
C9	0.1614 (2)	0.7946 (3)	−0.4726 (2)	0.0187 (5)
H9	0.1418	0.7034	−0.4731	0.022*
C10	0.1051 (2)	0.8690 (4)	−0.5551 (3)	0.0276 (7)
H10A	0.1072	0.8297	−0.6286	0.033*
H10B	0.0447	0.8660	−0.5353	0.033*
C22	0.5309 (2)	0.8700 (3)	0.0011 (3)	0.0271 (7)
H22A	0.5706	0.7997	−0.0117	0.041*
H22B	0.5634	0.9428	0.0338	0.041*
H22C	0.5008	0.8963	−0.0689	0.041*
C23	0.4885 (2)	0.8532 (3)	0.1934 (2)	0.0236 (6)
H23A	0.4342	0.8673	0.2285	0.028*
H23B	0.5225	0.9334	0.2009	0.028*
C24	0.5384 (2)	0.7476 (3)	0.2535 (2)	0.0237 (6)
C25	0.5179 (2)	0.6193 (3)	0.2364 (3)	0.0303 (7)
H25	0.4731	0.5957	0.1828	0.036*
C26	0.5629 (3)	0.5256 (4)	0.2975 (3)	0.0446 (10)
H26	0.5492	0.4377	0.2854	0.054*
C27	0.6277 (3)	0.5598 (6)	0.3758 (4)	0.0575 (14)
H27	0.6576	0.4954	0.4186	0.069*
C28	0.6491 (3)	0.6857 (7)	0.3924 (3)	0.0567 (14)
H28	0.6946	0.7081	0.4454	0.068*
C29	0.6043 (2)	0.7817 (5)	0.3317 (3)	0.0382 (8)
H29	0.6187	0.8693	0.3437	0.046*
C51	0.2551 (2)	0.5285 (3)	0.0642 (2)	0.0175 (5)
C52	0.2795 (2)	0.3714 (3)	0.2112 (2)	0.0226 (6)
C53	0.2308 (2)	0.2698 (4)	0.1692 (2)	0.0324 (7)
H53	0.1849	0.2839	0.1144	0.039*
C54	0.2493 (3)	0.1466 (4)	0.2075 (3)	0.0481 (11)
H54	0.2161	0.0762	0.1784	0.058*
C55	0.3155 (3)	0.1262 (4)	0.2873 (3)	0.0505 (11)
H55	0.3279	0.0419	0.3133	0.061*
C57	0.3454 (2)	0.3513 (4)	0.2916 (3)	0.0373 (8)
H57	0.3785	0.4215	0.3212	0.045*
C56	0.3633 (3)	0.2277 (5)	0.3292 (4)	0.0507 (11)
H56	0.4089	0.2135	0.3842	0.061*
C58	0.1438 (2)	0.7007 (3)	0.0454 (2)	0.0165 (5)
C59	0.1153 (2)	0.7933 (3)	0.1158 (2)	0.0217 (6)
H59	0.1560	0.8429	0.1598	0.026*
C61	0.2365 (2)	1.0122 (3)	−0.0907 (2)	0.0183 (5)
C62	0.2928 (2)	1.1269 (3)	−0.0926 (3)	0.0328 (7)
H62A	0.3036	1.1469	−0.1686	0.049*
H62B	0.3477	1.1096	−0.0500	0.049*
H62C	0.2644	1.1999	−0.0603	0.049*
C71	0.1990 (2)	0.5286 (3)	−0.3248 (2)	0.0216 (6)
C72	0.1585 (2)	0.4081 (3)	−0.2868 (3)	0.0328 (7)
H72A	0.0967	0.4094	−0.3090	0.049*
H72B	0.1674	0.4023	−0.2066	0.049*
H72C	0.1850	0.3340	−0.3200	0.049*
C81	0.0582 (2)	0.9887 (3)	−0.2948 (2)	0.0219 (6)
C82	−0.0318 (2)	0.9933 (4)	−0.2613 (3)	0.0379 (8)
H82A	−0.0424	0.9182	−0.2161	0.057*
H82B	−0.0724	0.9932	−0.3270	0.057*
H82C	−0.0398	1.0715	−0.2189	0.057*
C91	0.2788 (2)	0.7146 (3)	−0.5683 (2)	0.0271 (7)
C92	0.3751 (2)	0.7080 (4)	−0.5570 (3)	0.0426 (9)
H92A	0.3942	0.6622	−0.4894	0.064*
H92B	0.3988	0.7951	−0.5540	0.064*
H92C	0.3953	0.6626	−0.6202	0.064*
C101	0.0727 (2)	1.0924 (4)	−0.5534 (3)	0.0338 (8)
C102	0.1120 (3)	1.2211 (4)	−0.5581 (4)	0.0468 (10)
H10C	0.1502	1.2238	−0.6179	0.070*
H10D	0.1452	1.2393	−0.4883	0.070*
H10E	0.0665	1.2855	−0.5712	0.070*
C510	0.0274 (2)	0.8139 (3)	0.1224 (3)	0.0270 (7)
H510	0.0085	0.8768	0.1714	0.032*
C511	−0.0320 (2)	0.7432 (4)	0.0580 (3)	0.0295 (7)
H511	−0.0919	0.7581	0.0620	0.035*
C512	−0.0047 (2)	0.6511 (4)	−0.0120 (3)	0.0306 (7)
H512	−0.0458	0.6023	−0.0563	0.037*
C513	0.0830 (2)	0.6293 (3)	−0.0180 (2)	0.0240 (6)
H513	0.1015	0.5651	−0.0660	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0185 (3)	0.0178 (3)	0.0157 (3)	−0.0016 (3)	0.0024 (2)	−0.0042 (3)
O31	0.0161 (9)	0.0224 (11)	0.0367 (12)	0.0022 (8)	0.0036 (8)	−0.0031 (10)
O32	0.0292 (11)	0.048 (2)	0.0206 (10)	0.0134 (11)	0.0027 (8)	−0.0080 (11)
O51	0.0478 (13)	0.0181 (11)	0.0169 (10)	0.0027 (10)	0.0054 (9)	−0.0006 (9)
O61	0.0177 (8)	0.0129 (9)	0.0189 (9)	−0.0006 (8)	0.0041 (7)	−0.0019 (8)
O62	0.0329 (11)	0.0216 (11)	0.0357 (12)	−0.0019 (10)	0.0174 (9)	−0.0064 (10)
O71	0.0218 (9)	0.0153 (10)	0.0188 (9)	−0.0023 (8)	0.0015 (7)	−0.0027 (8)
O72	0.0377 (12)	0.0213 (12)	0.0268 (11)	0.0040 (10)	0.0073 (9)	−0.0050 (9)
O81	0.0158 (9)	0.0182 (10)	0.0226 (9)	0.0030 (8)	0.0033 (7)	−0.0028 (8)
O82	0.0329 (12)	0.0206 (12)	0.0411 (13)	0.0035 (10)	0.0031 (10)	−0.0035 (11)
O91	0.0245 (9)	0.0229 (11)	0.0178 (9)	0.0002 (9)	0.0064 (7)	−0.0018 (8)
O92	0.0494 (14)	0.0369 (15)	0.0220 (10)	−0.0014 (12)	0.0081 (10)	−0.0101 (11)
O101	0.0319 (11)	0.0289 (13)	0.0292 (11)	0.0098 (10)	0.0066 (9)	0.0115 (10)
O102	0.0353 (13)	0.061 (2)	0.059 (2)	0.0183 (14)	−0.0044 (12)	−0.003 (2)
N2	0.0197 (11)	0.0177 (12)	0.0236 (12)	−0.0020 (9)	0.0010 (9)	−0.0004 (10)
N3	0.0212 (11)	0.0192 (13)	0.0227 (11)	0.0031 (10)	0.0045 (9)	0.0015 (10)
N5	0.0349 (13)	0.0129 (12)	0.0162 (11)	0.0002 (10)	0.0027 (9)	0.0018 (10)
C2	0.0140 (10)	0.0148 (13)	0.0205 (11)	0.0022 (11)	0.0028 (9)	0.0035 (12)
C3	0.0170 (12)	0.0160 (14)	0.0176 (12)	0.0005 (11)	0.0044 (10)	0.0027 (11)
C4	0.0159 (11)	0.0166 (13)	0.0116 (11)	0.0013 (10)	0.0039 (9)	−0.0008 (10)
C5	0.0201 (12)	0.0147 (13)	0.0114 (11)	−0.0002 (10)	0.0023 (9)	0.0001 (10)
C6	0.0141 (10)	0.0118 (13)	0.0149 (11)	−0.0001 (10)	0.0010 (8)	−0.0009 (10)
C7	0.0162 (11)	0.0158 (14)	0.0153 (11)	−0.0013 (10)	0.0027 (9)	−0.0012 (10)
C8	0.0173 (12)	0.0193 (14)	0.0147 (12)	0.0000 (11)	0.0042 (9)	−0.0003 (11)
C9	0.0213 (12)	0.0200 (15)	0.0148 (11)	−0.0004 (11)	0.0015 (9)	−0.0012 (11)
C10	0.0261 (15)	0.033 (2)	0.0235 (14)	0.0026 (14)	−0.0004 (12)	0.0030 (14)
C22	0.0230 (13)	0.023 (2)	0.037 (2)	−0.0072 (13)	0.0101 (13)	−0.0007 (14)
C23	0.0207 (13)	0.022 (2)	0.0274 (14)	−0.0022 (12)	−0.0015 (11)	−0.0038 (13)
C24	0.0168 (12)	0.031 (2)	0.0240 (13)	0.0001 (12)	0.0038 (11)	0.0032 (12)
C25	0.0247 (14)	0.029 (2)	0.039 (2)	0.0057 (14)	0.0098 (13)	0.0061 (15)
C26	0.049 (2)	0.042 (2)	0.047 (2)	0.021 (2)	0.026 (2)	0.019 (2)
C27	0.047 (2)	0.086 (4)	0.041 (2)	0.035 (3)	0.016 (2)	0.037 (2)
C28	0.034 (2)	0.104 (5)	0.032 (2)	0.011 (2)	−0.0027 (15)	0.016 (2)
C29	0.0261 (14)	0.058 (2)	0.030 (2)	−0.001 (2)	−0.0013 (12)	0.002 (2)
C51	0.0176 (12)	0.0180 (14)	0.0169 (12)	0.0005 (10)	0.0014 (10)	0.0008 (11)
C52	0.0337 (15)	0.0181 (15)	0.0171 (13)	0.0061 (12)	0.0079 (11)	0.0057 (11)
C53	0.057 (2)	0.020 (2)	0.0202 (13)	−0.002 (2)	0.0009 (13)	0.0016 (14)
C54	0.097 (3)	0.020 (2)	0.029 (2)	−0.005 (2)	0.012 (2)	0.0009 (15)
C55	0.085 (3)	0.026 (2)	0.043 (2)	0.021 (2)	0.019 (2)	0.013 (2)
C57	0.040 (2)	0.035 (2)	0.035 (2)	−0.002 (2)	−0.0045 (15)	0.014 (2)
C56	0.051 (2)	0.053 (3)	0.047 (2)	0.013 (2)	0.002 (2)	0.029 (2)
C58	0.0167 (11)	0.0181 (14)	0.0150 (11)	−0.0008 (10)	0.0028 (9)	0.0056 (10)
C59	0.0205 (12)	0.021 (2)	0.0240 (13)	−0.0003 (12)	0.0040 (10)	−0.0003 (12)
C61	0.0230 (13)	0.0162 (14)	0.0158 (12)	0.0032 (11)	0.0026 (10)	0.0012 (11)
C62	0.038 (2)	0.022 (2)	0.040 (2)	−0.0061 (15)	0.0143 (14)	−0.0115 (15)
C71	0.0276 (14)	0.0191 (15)	0.0173 (12)	0.0009 (12)	−0.0026 (11)	−0.0024 (11)
C72	0.046 (2)	0.019 (2)	0.033 (2)	−0.0035 (15)	0.0053 (14)	−0.0049 (14)
C81	0.0234 (13)	0.023 (2)	0.0194 (13)	0.0079 (12)	0.0003 (11)	−0.0042 (12)
C82	0.029 (2)	0.038 (2)	0.047 (2)	0.006 (2)	0.0072 (14)	−0.017 (2)
C91	0.034 (2)	0.027 (2)	0.0210 (14)	0.0017 (14)	0.0123 (12)	−0.0010 (13)
C92	0.036 (2)	0.048 (2)	0.047 (2)	0.001 (2)	0.019 (2)	−0.011 (2)
C101	0.036 (2)	0.042 (2)	0.0234 (15)	0.016 (2)	−0.0028 (13)	0.0058 (15)
C102	0.052 (2)	0.041 (2)	0.048 (2)	0.020 (2)	0.008 (2)	0.012 (2)
C510	0.0255 (14)	0.025 (2)	0.0315 (15)	0.0063 (12)	0.0091 (12)	0.0002 (13)
C511	0.0176 (13)	0.040 (2)	0.032 (2)	0.0031 (13)	0.0052 (11)	0.0056 (14)
C512	0.0202 (13)	0.042 (2)	0.029 (2)	−0.0058 (14)	0.0018 (11)	−0.005 (2)
C513	0.0220 (13)	0.028 (2)	0.0223 (13)	−0.0027 (13)	0.0055 (11)	−0.0059 (13)

Geometric parameters (Å, º)

S1—C2	1.766 (2)	C25—C26	1.386 (5)
S1—C5	1.838 (3)	C25—H25	0.9500
O31—N3	1.243 (3)	C26—C27	1.380 (7)
O32—N3	1.249 (3)	C26—H26	0.9500
O51—C51	1.215 (4)	C27—C28	1.365 (9)
O61—C61	1.362 (3)	C27—H27	0.9500
O61—C6	1.436 (3)	C28—C29	1.400 (7)
O62—C61	1.193 (3)	C28—H28	0.9500
O71—C71	1.362 (4)	C29—H29	0.9500
O71—C7	1.449 (3)	C52—C53	1.379 (5)
O72—C71	1.202 (4)	C52—C57	1.378 (5)
O81—C81	1.376 (4)	C53—C54	1.390 (5)
O81—C8	1.442 (3)	C53—H53	0.9500
O82—C81	1.198 (4)	C54—C55	1.376 (6)
O91—C91	1.344 (4)	C54—H54	0.9500
O91—C9	1.447 (3)	C55—C56	1.370 (7)
O92—C91	1.204 (4)	C55—H55	0.9500
O101—C101	1.352 (4)	C57—C56	1.389 (6)
O101—C10	1.442 (5)	C57—H57	0.9500
O102—C101	1.203 (4)	C56—H56	0.9500
N2—C2	1.340 (3)	C58—C513	1.390 (4)
N2—C22	1.468 (4)	C58—C59	1.391 (4)
N2—C23	1.470 (4)	C59—C510	1.394 (4)
N3—C3	1.402 (3)	C59—H59	0.9500
N5—C51	1.351 (3)	C61—C62	1.486 (4)
N5—C52	1.430 (4)	C62—H62A	0.9800
N5—H5	0.8800	C62—H62B	0.9800
C2—C3	1.384 (4)	C62—H62C	0.9800
C3—C4	1.508 (3)	C71—C72	1.496 (5)
C4—C6	1.551 (4)	C72—H72A	0.9800
C4—C5	1.566 (3)	C72—H72B	0.9800
C4—H4	1.0000	C72—H72C	0.9800
C5—C58	1.523 (4)	C81—C82	1.492 (4)
C5—C51	1.573 (4)	C82—H82A	0.9800
C6—C7	1.543 (3)	C82—H82B	0.9800
C6—H6	1.0000	C82—H82C	0.9800
C7—C8	1.519 (4)	C91—C92	1.497 (5)
C7—H7	1.0000	C92—H92A	0.9800
C8—C9	1.539 (4)	C92—H92B	0.9800
C8—H8	1.0000	C92—H92C	0.9800
C9—C10	1.498 (4)	C101—C102	1.479 (6)
C9—H9	1.0000	C102—H10C	0.9800
C10—H10A	0.9900	C102—H10D	0.9800
C10—H10B	0.9900	C102—H10E	0.9800
C22—H22A	0.9800	C510—C511	1.380 (5)
C22—H22B	0.9800	C510—H510	0.9500
C22—H22C	0.9800	C511—C512	1.377 (5)
C23—C24	1.505 (4)	C511—H511	0.9500
C23—H23A	0.9900	C512—C513	1.394 (4)
C23—H23B	0.9900	C512—H512	0.9500
C24—C25	1.388 (5)	C513—H513	0.9500
C24—C29	1.390 (4)
C2—S1—C5	92.53 (12)	C29—C28—H28	119.8
C61—O61—C6	117.5 (2)	C24—C29—C28	119.3 (4)
C71—O71—C7	117.8 (2)	C24—C29—H29	120.4
C81—O81—C8	117.1 (2)	C28—C29—H29	120.4
C91—O91—C9	118.4 (2)	O51—C51—N5	123.5 (3)
C101—O101—C10	117.2 (3)	O51—C51—C5	120.1 (2)
C2—N2—C22	122.2 (2)	N5—C51—C5	116.3 (2)
C2—N2—C23	121.3 (2)	C53—C52—C57	120.3 (3)
C22—N2—C23	116.4 (2)	C53—C52—N5	121.2 (3)
O31—N3—O32	121.6 (2)	C57—C52—N5	118.6 (3)
O31—N3—C3	120.6 (2)	C52—C53—C54	119.5 (3)
O32—N3—C3	117.7 (2)	C52—C53—H53	120.2
C51—N5—C52	122.5 (2)	C54—C53—H53	120.2
C51—N5—H5	118.7	C55—C54—C53	120.3 (4)
C52—N5—H5	118.7	C55—C54—H54	119.9
N2—C2—C3	131.1 (2)	C53—C54—H54	119.9
N2—C2—S1	117.8 (2)	C56—C55—C54	119.9 (4)
C3—C2—S1	110.9 (2)	C56—C55—H55	120.1
C2—C3—N3	123.7 (2)	C54—C55—H55	120.1
C2—C3—C4	116.2 (2)	C52—C57—C56	119.6 (4)
N3—C3—C4	119.1 (2)	C52—C57—H57	120.2
C3—C4—C6	115.2 (2)	C56—C57—H57	120.2
C3—C4—C5	104.1 (2)	C55—C56—C57	120.4 (4)
C6—C4—C5	116.0 (2)	C55—C56—H56	119.8
C3—C4—H4	107.0	C57—C56—H56	119.8
C6—C4—H4	107.0	C513—C58—C59	118.7 (2)
C5—C4—H4	107.0	C513—C58—C5	118.5 (3)
C58—C5—C4	115.8 (2)	C59—C58—C5	122.9 (2)
C58—C5—C51	107.3 (2)	C58—C59—C510	120.5 (3)
C4—C5—C51	106.5 (2)	C58—C59—H59	119.7
C58—C5—S1	110.88 (19)	C510—C59—H59	119.7
C4—C5—S1	105.05 (18)	O62—C61—O61	123.0 (3)
C51—C5—S1	111.23 (17)	O62—C61—C62	126.3 (3)
O61—C6—C7	106.6 (2)	O61—C61—C62	110.7 (2)
O61—C6—C4	111.4 (2)	C61—C62—H62A	109.5
C7—C6—C4	109.9 (2)	C61—C62—H62B	109.5
O61—C6—H6	109.7	H62A—C62—H62B	109.5
C7—C6—H6	109.7	C61—C62—H62C	109.5
C4—C6—H6	109.7	H62A—C62—H62C	109.5
O71—C7—C8	110.8 (2)	H62B—C62—H62C	109.5
O71—C7—C6	103.9 (2)	O72—C71—O71	123.9 (3)
C8—C7—C6	113.7 (2)	O72—C71—C72	126.2 (3)
O71—C7—H7	109.4	O71—C71—C72	109.8 (2)
C8—C7—H7	109.4	C71—C72—H72A	109.5
C6—C7—H7	109.4	C71—C72—H72B	109.5
O81—C8—C7	110.0 (2)	H72A—C72—H72B	109.5
O81—C8—C9	109.0 (2)	C71—C72—H72C	109.5
C7—C8—C9	110.5 (2)	H72A—C72—H72C	109.5
O81—C8—H8	109.1	H72B—C72—H72C	109.5
C7—C8—H8	109.1	O82—C81—O81	123.2 (2)
C9—C8—H8	109.1	O82—C81—C82	126.1 (3)
O91—C9—C10	112.0 (2)	O81—C81—C82	110.7 (3)
O91—C9—C8	101.5 (2)	C81—C82—H82A	109.5
C10—C9—C8	115.7 (3)	C81—C82—H82B	109.5
O91—C9—H9	109.1	H82A—C82—H82B	109.5
C10—C9—H9	109.1	C81—C82—H82C	109.5
C8—C9—H9	109.1	H82A—C82—H82C	109.5
O101—C10—C9	110.3 (3)	H82B—C82—H82C	109.5
O101—C10—H10A	109.6	O92—C91—O91	123.6 (3)
C9—C10—H10A	109.6	O92—C91—C92	126.4 (3)
O101—C10—H10B	109.6	O91—C91—C92	110.0 (3)
C9—C10—H10B	109.6	C91—C92—H92A	109.5
H10A—C10—H10B	108.1	C91—C92—H92B	109.5
N2—C22—H22A	109.5	H92A—C92—H92B	109.5
N2—C22—H22B	109.5	C91—C92—H92C	109.5
H22A—C22—H22B	109.5	H92A—C92—H92C	109.5
N2—C22—H22C	109.5	H92B—C92—H92C	109.5
H22A—C22—H22C	109.5	O102—C101—O101	123.3 (4)
H22B—C22—H22C	109.5	O102—C101—C102	126.2 (4)
N2—C23—C24	113.8 (3)	O101—C101—C102	110.5 (3)
N2—C23—H23A	108.8	C101—C102—H10C	109.5
C24—C23—H23A	108.8	C101—C102—H10D	109.5
N2—C23—H23B	108.8	H10C—C102—H10D	109.5
C24—C23—H23B	108.8	C101—C102—H10E	109.5
H23A—C23—H23B	107.7	H10C—C102—H10E	109.5
C25—C24—C29	119.9 (3)	H10D—C102—H10E	109.5
C25—C24—C23	122.0 (3)	C511—C510—C59	120.0 (3)
C29—C24—C23	118.1 (3)	C511—C510—H510	120.0
C26—C25—C24	119.9 (3)	C59—C510—H510	120.0
C26—C25—H25	120.0	C512—C511—C510	120.1 (3)
C24—C25—H25	120.0	C512—C511—H511	120.0
C27—C26—C25	120.0 (4)	C510—C511—H511	120.0
C27—C26—H26	120.0	C511—C512—C513	120.0 (3)
C25—C26—H26	120.0	C511—C512—H512	120.0
C28—C27—C26	120.5 (4)	C513—C512—H512	120.0
C28—C27—H27	119.7	C58—C513—C512	120.7 (3)
C26—C27—H27	119.7	C58—C513—H513	119.7
C27—C28—C29	120.3 (4)	C512—C513—H513	119.7
C27—C28—H28	119.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O32	1.00	2.294	3.076 (3)	134
C9—H9···O72	1.00	2.597	3.172 (4)	116
C22—H22A···O31	0.98	2.187	2.676 (4)	109
C53—H53···O51	0.95	2.593	2.916 (4)	100
N5—H5···O92^i	0.88	2.125	2.966 (4)	160
C23—H23B···O31^ii	0.99	2.541	3.265 (5)	130
C22—H22B···O31^ii	0.98	2.496	3.171 (5)	126
C511—H511···O62^iii	0.95	2.971	3.350 (4)	105
C512—H512···O62^iii	0.95	2.627	3.176 (4)	117

Symmetry codes: (i) x, y, z+1; (ii) −x+1, y+1/2, −z; (iii) −x, y−1/2, −z.