The crystal structure of the title compound, C
40H
43N
3O
13S, 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.
Supporting information
CCDC reference: 177239
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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.
(4
R,5
R)-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
top
Crystal data top
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) Å3 | Prism, yellow |
Z = 2 | 0.40 × 0.28 × 0.24 mm |
F(000) = 848 | |
Data collection top
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 top
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)] = 0.041 | H-atom parameters not refined |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0726P)2] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O92i | 0.88 | 2.125 | 2.966 (4) | 160 |
C23—H23B···O31ii | 0.99 | 2.541 | 3.265 (5) | 130 |
C22—H22B···O31ii | 0.98 | 2.496 | 3.171 (5) | 126 |
C511—H511···O62iii | 0.95 | 2.971 | 3.350 (4) | 105 |
C512—H512···O62iii | 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. |