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The title molecular complex, C5H12NO2S+·C8H7O3-·2C8H8O3, contains (R)-methioninium cations, (R)-mandelate anions and (R)-mandelic acid molecules. The (R)-methioninium cation assumes an anti conformation for all of its single bonds. Hydrophilic and hydrophobic layers alternate in the crystal structure. Hydrogen-bond interactions and van der Waals contacts occur in the hydrophilic and hydrophobic layers, respectively.
Supporting information
CCDC reference: 274621
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.015 Å
- R factor = 0.086
- wR factor = 0.250
- Data-to-parameter ratio = 7.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 15
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc.
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.83
PLAT213_ALERT_2_C Atom C11 has ADP max/min Ratio ............. 3.60 prolat
PLAT213_ALERT_2_C Atom C23 has ADP max/min Ratio ............. 3.40 prolat
PLAT213_ALERT_2_C Atom C33 has ADP max/min Ratio ............. 3.80 oblate
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C16
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.27
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.46
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.14
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.06
PLAT432_ALERT_2_C Short Inter X...Y Contact C11 .. C21 .. 3.15 Ang.
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C29 H35 N1 O11 S1
Atom count from _chemical_formula_moiety:C29 H35 N1 O11
REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
From the CIF: _diffrn_reflns_theta_max 25.00
From the CIF: _reflns_number_total 2974
Count of symmetry unique reflns 2975
Completeness (_total/calc) 99.97%
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
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
13 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
9 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1993); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C5H12NO2S+·C8H7O3−·C8H8O3 | F(000) = 1280 |
Mr = 605.65 | Dx = 1.363 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 9.562 (3) Å | θ = 5.6–14.6° |
b = 9.830 (3) Å | µ = 0.17 mm−1 |
c = 31.393 (5) Å | T = 298 K |
V = 2950.8 (14) Å3 | Prism, colorless |
Z = 4 | 0.20 × 0.18 × 0.16 mm |
Data collection top
Rigaku AFC-7S diffractometer | 1383 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 25.0°, θmin = 2.2° |
Detector resolution: 3 pixels mm-1 | h = −5→11 |
ω/2θ scans | k = −5→11 |
3416 measured reflections | l = −19→37 |
2974 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.086 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.250 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.136P)2] where P = (Fo2 + 2Fc2)/3 |
2974 reflections | (Δ/σ)max < 0.001 |
380 parameters | Δρmax = 0.42 e Å−3 |
234 restraints | Δρmin = −0.48 e Å−3 |
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 | Uiso*/Ueq | |
S | 0.5694 (4) | 0.3925 (4) | 0.07515 (9) | 0.0748 (12) | |
O1 | 0.7771 (8) | 0.3428 (8) | 0.2153 (2) | 0.055 (2) | |
H1 | 0.7995 | 0.2697 | 0.2346 | 0.080* | |
O2 | 0.5594 (8) | 0.3282 (7) | 0.24108 (18) | 0.047 (2) | |
O11 | 0.9952 (7) | 1.0870 (7) | 0.18233 (19) | 0.0413 (18) | |
H11 | 1.0858 | 1.0912 | 0.1950 | 0.080* | |
O12 | 1.0059 (8) | 0.8825 (7) | 0.21361 (19) | 0.048 (2) | |
O13 | 0.7253 (8) | 0.8458 (7) | 0.20166 (19) | 0.047 (2) | |
H13 | 0.7336 | 0.8576 | 0.2291 | 0.080* | |
O21 | −0.0285 (7) | 0.6178 (8) | 0.20412 (19) | 0.0460 (19) | |
H21 | −0.0258 | 0.7154 | 0.2128 | 0.080* | |
O22 | 0.1891 (8) | 0.6227 (7) | 0.23157 (19) | 0.0453 (19) | |
O23 | 0.2497 (7) | 0.3827 (7) | 0.20448 (17) | 0.0386 (17) | |
H23 | 0.2784 | 0.3213 | 0.1863 | 0.080* | |
O31 | 0.4753 (9) | 1.0613 (8) | 0.1917 (2) | 0.051 (2) | |
O32 | 0.2541 (8) | 1.1170 (8) | 0.1855 (2) | 0.052 (2) | |
O33 | 0.4447 (8) | 0.8107 (6) | 0.16652 (18) | 0.0385 (17) | |
H33 | 0.5301 | 0.8604 | 0.1713 | 0.080* | |
N | 0.4853 (10) | 0.5696 (9) | 0.2144 (2) | 0.048 (2) | |
H1A | 0.4855 | 0.5745 | 0.2427 | 0.071* | |
H1B | 0.4186 | 0.5124 | 0.2060 | 0.071* | |
H1C | 0.4689 | 0.6517 | 0.2036 | 0.071* | |
C1 | 0.6473 (10) | 0.3811 (12) | 0.2212 (3) | 0.036 (3) | |
C2 | 0.6240 (11) | 0.5195 (11) | 0.1993 (3) | 0.037 (3) | |
H2 | 0.6962 | 0.5827 | 0.2092 | 0.044* | |
C3 | 0.6350 (11) | 0.5079 (11) | 0.1511 (3) | 0.044 (3) | |
H3A | 0.7312 | 0.4878 | 0.1437 | 0.052* | |
H3B | 0.6115 | 0.5952 | 0.1386 | 0.052* | |
C4 | 0.5397 (12) | 0.3979 (12) | 0.1313 (3) | 0.052 (3) | |
H4A | 0.4424 | 0.4192 | 0.1369 | 0.062* | |
H4B | 0.5604 | 0.3099 | 0.1438 | 0.062* | |
C5 | 0.4372 (15) | 0.2709 (14) | 0.0596 (4) | 0.082 (5) | |
H5A | 0.4271 | 0.2717 | 0.0292 | 0.123* | |
H5B | 0.3497 | 0.2947 | 0.0726 | 0.123* | |
H5C | 0.4646 | 0.1816 | 0.0688 | 0.123* | |
C11 | 0.9441 (13) | 0.9709 (11) | 0.1943 (3) | 0.044 (3) | |
C12 | 0.7902 (12) | 0.9568 (10) | 0.1805 (2) | 0.042 (3) | |
H12 | 0.7398 | 1.0409 | 0.1872 | 0.050* | |
C13 | 0.7901 (11) | 0.9346 (10) | 0.1329 (2) | 0.035 (2) | |
C14 | 0.7548 (13) | 1.0399 (11) | 0.1058 (3) | 0.055 (3) | |
H14 | 0.7252 | 1.1230 | 0.1167 | 0.066* | |
C15 | 0.7640 (15) | 1.0205 (15) | 0.0615 (3) | 0.066 (4) | |
H15 | 0.7471 | 1.0927 | 0.0431 | 0.079* | |
C16 | 0.7973 (15) | 0.8977 (16) | 0.0458 (4) | 0.083 (5) | |
H16 | 0.7964 | 0.8840 | 0.0165 | 0.099* | |
C17 | 0.8329 (14) | 0.7906 (13) | 0.0725 (3) | 0.068 (4) | |
H17 | 0.8597 | 0.7071 | 0.0612 | 0.082* | |
C18 | 0.8282 (13) | 0.8094 (11) | 0.1162 (3) | 0.052 (3) | |
H18 | 0.8506 | 0.7379 | 0.1344 | 0.062* | |
C21 | 0.0976 (10) | 0.5700 (12) | 0.2111 (3) | 0.035 (3) | |
C22 | 0.1168 (10) | 0.4307 (10) | 0.1901 (3) | 0.033 (2) | |
H22 | 0.0436 | 0.3689 | 0.2003 | 0.039* | |
C23 | 0.1075 (12) | 0.4425 (10) | 0.1419 (3) | 0.042 (3) | |
C24 | 0.1807 (12) | 0.5447 (11) | 0.1206 (3) | 0.052 (3) | |
H24 | 0.2363 | 0.6046 | 0.1361 | 0.062* | |
C25 | 0.1717 (14) | 0.5579 (12) | 0.0772 (3) | 0.062 (4) | |
H25 | 0.2211 | 0.6262 | 0.0633 | 0.074* | |
C26 | 0.0899 (14) | 0.4703 (15) | 0.0547 (3) | 0.070 (4) | |
H26 | 0.0861 | 0.4771 | 0.0251 | 0.083* | |
C27 | 0.0122 (14) | 0.3711 (13) | 0.0753 (3) | 0.062 (4) | |
H27 | −0.0456 | 0.3129 | 0.0599 | 0.075* | |
C28 | 0.0219 (12) | 0.3598 (12) | 0.1193 (3) | 0.048 (3) | |
H28 | −0.0311 | 0.2946 | 0.1334 | 0.058* | |
C31 | 0.3593 (13) | 1.0424 (12) | 0.1789 (3) | 0.040 (3) | |
C32 | 0.3286 (11) | 0.9033 (11) | 0.1578 (2) | 0.037 (3) | |
H32 | 0.2426 | 0.8655 | 0.1699 | 0.045* | |
C33 | 0.3110 (12) | 0.9169 (11) | 0.1096 (3) | 0.044 (3) | |
C34 | 0.1916 (13) | 0.9750 (14) | 0.0928 (3) | 0.064 (4) | |
H34 | 0.1213 | 1.0037 | 0.1112 | 0.077* | |
C35 | 0.1734 (15) | 0.9918 (15) | 0.0494 (4) | 0.075 (4) | |
H35 | 0.0943 | 1.0355 | 0.0390 | 0.090* | |
C36 | 0.2743 (13) | 0.9427 (14) | 0.0218 (3) | 0.067 (4) | |
H36 | 0.2629 | 0.9517 | −0.0075 | 0.080* | |
C37 | 0.3920 (14) | 0.8805 (13) | 0.0381 (3) | 0.066 (4) | |
H37 | 0.4597 | 0.8459 | 0.0198 | 0.079* | |
C38 | 0.4090 (12) | 0.8697 (11) | 0.0815 (3) | 0.047 (3) | |
H38 | 0.4897 | 0.8289 | 0.0920 | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S | 0.105 (3) | 0.089 (3) | 0.0302 (14) | −0.007 (3) | 0.0112 (17) | −0.0053 (18) |
O1 | 0.062 (5) | 0.056 (5) | 0.047 (4) | 0.004 (5) | 0.006 (4) | 0.021 (4) |
O2 | 0.055 (5) | 0.059 (5) | 0.028 (3) | 0.007 (4) | 0.015 (4) | 0.012 (3) |
O11 | 0.053 (5) | 0.035 (4) | 0.037 (4) | 0.002 (4) | −0.008 (3) | 0.003 (3) |
O12 | 0.071 (5) | 0.038 (4) | 0.036 (4) | 0.003 (4) | 0.000 (4) | 0.004 (4) |
O13 | 0.068 (5) | 0.049 (4) | 0.023 (3) | −0.003 (4) | −0.006 (4) | 0.003 (3) |
O21 | 0.047 (5) | 0.053 (5) | 0.038 (4) | −0.003 (4) | −0.006 (3) | −0.006 (4) |
O22 | 0.057 (5) | 0.050 (4) | 0.030 (3) | 0.000 (4) | −0.010 (4) | −0.003 (3) |
O23 | 0.052 (5) | 0.039 (4) | 0.024 (3) | −0.004 (4) | −0.010 (3) | −0.006 (3) |
O31 | 0.075 (6) | 0.045 (5) | 0.031 (4) | 0.007 (5) | −0.016 (4) | 0.003 (3) |
O32 | 0.050 (5) | 0.052 (5) | 0.054 (4) | −0.001 (5) | 0.009 (4) | −0.013 (4) |
O33 | 0.055 (5) | 0.032 (4) | 0.029 (3) | 0.006 (4) | −0.009 (3) | 0.004 (3) |
N | 0.082 (7) | 0.035 (5) | 0.027 (4) | 0.000 (5) | 0.011 (5) | −0.003 (4) |
C1 | 0.023 (5) | 0.072 (8) | 0.015 (4) | 0.000 (6) | 0.010 (4) | −0.002 (5) |
C2 | 0.051 (7) | 0.039 (6) | 0.021 (5) | 0.002 (6) | 0.011 (5) | 0.008 (4) |
C3 | 0.060 (7) | 0.048 (7) | 0.023 (5) | 0.003 (6) | 0.010 (5) | 0.007 (5) |
C4 | 0.067 (8) | 0.060 (7) | 0.029 (5) | 0.003 (8) | 0.004 (5) | 0.002 (5) |
C5 | 0.091 (11) | 0.100 (11) | 0.056 (7) | 0.013 (10) | −0.033 (8) | −0.037 (8) |
C11 | 0.084 (9) | 0.041 (6) | 0.007 (4) | 0.007 (7) | −0.001 (5) | 0.003 (4) |
C12 | 0.084 (8) | 0.029 (5) | 0.013 (4) | 0.002 (6) | −0.003 (5) | 0.002 (4) |
C13 | 0.050 (6) | 0.045 (6) | 0.012 (4) | −0.002 (6) | −0.013 (4) | 0.000 (4) |
C14 | 0.086 (9) | 0.050 (7) | 0.029 (5) | 0.007 (8) | −0.006 (6) | 0.005 (5) |
C15 | 0.087 (10) | 0.078 (9) | 0.032 (6) | −0.008 (9) | −0.016 (6) | 0.009 (6) |
C16 | 0.102 (11) | 0.113 (13) | 0.033 (6) | 0.011 (11) | −0.027 (7) | −0.009 (8) |
C17 | 0.107 (10) | 0.069 (8) | 0.029 (5) | 0.015 (8) | −0.008 (7) | −0.027 (6) |
C18 | 0.087 (9) | 0.045 (6) | 0.024 (5) | −0.002 (7) | −0.008 (6) | −0.009 (5) |
C21 | 0.021 (5) | 0.070 (8) | 0.014 (4) | −0.002 (6) | −0.008 (4) | 0.004 (5) |
C22 | 0.042 (6) | 0.037 (6) | 0.019 (4) | −0.009 (5) | −0.018 (4) | −0.002 (4) |
C23 | 0.081 (8) | 0.034 (6) | 0.011 (4) | 0.005 (6) | −0.013 (5) | 0.005 (4) |
C24 | 0.079 (8) | 0.050 (7) | 0.026 (5) | −0.008 (7) | −0.003 (5) | 0.000 (5) |
C25 | 0.101 (10) | 0.058 (8) | 0.027 (5) | −0.010 (8) | 0.010 (6) | 0.003 (5) |
C26 | 0.093 (10) | 0.095 (10) | 0.020 (5) | 0.014 (10) | 0.010 (6) | 0.015 (6) |
C27 | 0.096 (9) | 0.061 (8) | 0.031 (5) | 0.003 (8) | −0.037 (6) | −0.009 (6) |
C28 | 0.067 (8) | 0.060 (7) | 0.018 (4) | −0.005 (7) | −0.008 (5) | 0.002 (5) |
C31 | 0.054 (7) | 0.049 (7) | 0.018 (5) | 0.002 (7) | −0.010 (5) | 0.003 (5) |
C32 | 0.051 (6) | 0.045 (6) | 0.016 (4) | −0.005 (6) | −0.008 (4) | 0.000 (4) |
C33 | 0.068 (8) | 0.049 (6) | 0.014 (4) | −0.011 (6) | −0.023 (5) | 0.004 (4) |
C34 | 0.067 (8) | 0.104 (10) | 0.021 (5) | −0.002 (8) | −0.003 (6) | −0.002 (6) |
C35 | 0.096 (10) | 0.089 (10) | 0.040 (7) | 0.008 (9) | −0.024 (7) | 0.012 (7) |
C36 | 0.088 (10) | 0.099 (10) | 0.015 (5) | −0.002 (10) | −0.006 (6) | 0.001 (6) |
C37 | 0.105 (10) | 0.071 (8) | 0.023 (5) | 0.000 (9) | −0.018 (6) | 0.001 (6) |
C38 | 0.064 (7) | 0.053 (7) | 0.022 (5) | 0.004 (7) | 0.000 (5) | 0.001 (5) |
Geometric parameters (Å, º) top
C1—O1 | 1.310 (12) | C13—C18 | 1.387 (14) |
C1—O2 | 1.170 (11) | C14—C15 | 1.406 (14) |
C11—O11 | 1.296 (12) | C14—H14 | 0.9300 |
C11—O12 | 1.214 (12) | C15—C16 | 1.342 (18) |
C21—O21 | 1.312 (11) | C15—H15 | 0.9300 |
C21—O22 | 1.204 (11) | C16—C17 | 1.389 (17) |
C31—O31 | 1.194 (12) | C16—H16 | 0.9300 |
C31—O32 | 1.262 (13) | C17—C18 | 1.384 (13) |
S—C4 | 1.785 (9) | C17—H17 | 0.9300 |
S—C5 | 1.807 (13) | C18—H18 | 0.9300 |
O1—H1 | 0.9645 | C21—C22 | 1.530 (15) |
O11—H11 | 0.9543 | C22—C23 | 1.521 (11) |
O13—C12 | 1.420 (11) | C22—H22 | 0.9800 |
O13—H13 | 0.8717 | C23—C28 | 1.354 (13) |
O21—H21 | 0.9978 | C23—C24 | 1.394 (14) |
O23—C22 | 1.428 (11) | C24—C25 | 1.371 (14) |
O23—H23 | 0.8746 | C24—H24 | 0.9300 |
O33—C32 | 1.462 (12) | C25—C26 | 1.362 (16) |
O33—H33 | 0.9637 | C25—H25 | 0.9300 |
N—C2 | 1.492 (12) | C26—C27 | 1.387 (17) |
N—H1A | 0.8900 | C26—H26 | 0.9300 |
N—H1B | 0.8900 | C27—C28 | 1.388 (13) |
N—H1C | 0.8900 | C27—H27 | 0.9300 |
C1—C2 | 1.541 (14) | C28—H28 | 0.9300 |
C2—C3 | 1.520 (12) | C31—C32 | 1.547 (14) |
C2—H2 | 0.9800 | C32—C33 | 1.526 (11) |
C3—C4 | 1.545 (15) | C32—H32 | 0.9800 |
C3—H3A | 0.9700 | C33—C38 | 1.369 (14) |
C3—H3B | 0.9700 | C33—C34 | 1.381 (15) |
C4—H4A | 0.9700 | C34—C35 | 1.383 (14) |
C4—H4B | 0.9700 | C34—H34 | 0.9300 |
C5—H5A | 0.9600 | C35—C36 | 1.385 (17) |
C5—H5B | 0.9600 | C35—H35 | 0.9300 |
C5—H5C | 0.9600 | C36—C37 | 1.379 (16) |
C11—C12 | 1.541 (16) | C36—H36 | 0.9300 |
C12—C13 | 1.509 (11) | C37—C38 | 1.376 (12) |
C12—H12 | 0.9800 | C37—H37 | 0.9300 |
C13—C14 | 1.383 (13) | C38—H38 | 0.9300 |
| | | |
C4—S—C5 | 100.1 (6) | C15—C16—H16 | 119.4 |
O1—C1—O2 | 129.0 (11) | C17—C16—H16 | 119.4 |
O11—C11—O12 | 126.3 (12) | C18—C17—C16 | 119.3 (11) |
O21—C21—O22 | 127.0 (11) | C18—C17—H17 | 120.4 |
O31—C31—O32 | 126.4 (11) | C16—C17—H17 | 120.4 |
C1—O1—H1 | 109.6 | C17—C18—C13 | 120.1 (10) |
C11—O11—H11 | 105.1 | C17—C18—H18 | 119.9 |
C12—O13—H13 | 108.6 | C13—C18—H18 | 119.9 |
C21—O21—H21 | 106.0 | O22—C21—C22 | 121.9 (9) |
C22—O23—H23 | 107.5 | O21—C21—C22 | 111.1 (8) |
C32—O33—H33 | 110.9 | O23—C22—C23 | 113.1 (8) |
C2—N—H1A | 109.5 | O23—C22—C21 | 105.5 (7) |
C2—N—H1B | 109.5 | C23—C22—C21 | 110.6 (8) |
H1A—N—H1B | 109.5 | O23—C22—H22 | 109.2 |
C2—N—H1C | 109.5 | C23—C22—H22 | 109.2 |
H1A—N—H1C | 109.5 | C21—C22—H22 | 109.2 |
H1B—N—H1C | 109.5 | C28—C23—C24 | 119.0 (8) |
O2—C1—C2 | 121.8 (10) | C28—C23—C22 | 120.7 (9) |
O1—C1—C2 | 109.1 (9) | C24—C23—C22 | 120.2 (9) |
N—C2—C3 | 113.8 (8) | C25—C24—C23 | 120.8 (11) |
N—C2—C1 | 106.1 (8) | C25—C24—H24 | 119.6 |
C3—C2—C1 | 111.6 (8) | C23—C24—H24 | 119.6 |
N—C2—H2 | 108.4 | C26—C25—C24 | 119.5 (11) |
C3—C2—H2 | 108.4 | C26—C25—H25 | 120.2 |
C1—C2—H2 | 108.4 | C24—C25—H25 | 120.2 |
C2—C3—C4 | 114.4 (9) | C25—C26—C27 | 120.6 (10) |
C2—C3—H3A | 108.7 | C25—C26—H26 | 119.7 |
C4—C3—H3A | 108.7 | C27—C26—H26 | 119.7 |
C2—C3—H3B | 108.7 | C26—C27—C28 | 119.0 (11) |
C4—C3—H3B | 108.7 | C26—C27—H27 | 120.5 |
H3A—C3—H3B | 107.6 | C28—C27—H27 | 120.5 |
C3—C4—S | 109.0 (7) | C23—C28—C27 | 120.9 (11) |
C3—C4—H4A | 109.9 | C23—C28—H28 | 119.5 |
S—C4—H4A | 109.9 | C27—C28—H28 | 119.5 |
C3—C4—H4B | 109.9 | O31—C31—C32 | 117.3 (11) |
S—C4—H4B | 109.9 | O32—C31—C32 | 115.7 (10) |
H4A—C4—H4B | 108.3 | O33—C32—C33 | 108.9 (8) |
S—C5—H5A | 109.5 | O33—C32—C31 | 109.0 (8) |
S—C5—H5B | 109.5 | C33—C32—C31 | 111.6 (8) |
H5A—C5—H5B | 109.5 | O33—C32—H32 | 109.1 |
S—C5—H5C | 109.5 | C33—C32—H32 | 109.1 |
H5A—C5—H5C | 109.5 | C31—C32—H32 | 109.1 |
H5B—C5—H5C | 109.5 | C38—C33—C34 | 117.3 (9) |
O12—C11—C12 | 122.7 (10) | C38—C33—C32 | 122.3 (10) |
O11—C11—C12 | 111.0 (9) | C34—C33—C32 | 120.3 (10) |
O13—C12—C13 | 110.6 (8) | C33—C34—C35 | 122.0 (12) |
O13—C12—C11 | 110.8 (8) | C33—C34—H34 | 119.0 |
C13—C12—C11 | 106.9 (8) | C35—C34—H34 | 119.0 |
O13—C12—H12 | 109.5 | C34—C35—C36 | 119.2 (13) |
C13—C12—H12 | 109.5 | C34—C35—H35 | 120.4 |
C11—C12—H12 | 109.5 | C36—C35—H35 | 120.4 |
C14—C13—C18 | 119.6 (8) | C37—C36—C35 | 119.3 (10) |
C14—C13—C12 | 120.2 (9) | C37—C36—H36 | 120.3 |
C18—C13—C12 | 120.2 (8) | C35—C36—H36 | 120.3 |
C13—C14—C15 | 119.6 (11) | C38—C37—C36 | 119.9 (12) |
C13—C14—H14 | 120.2 | C38—C37—H37 | 120.1 |
C15—C14—H14 | 120.2 | C36—C37—H37 | 120.1 |
C16—C15—C14 | 119.9 (12) | C33—C38—C37 | 122.1 (11) |
C16—C15—H15 | 120.0 | C33—C38—H38 | 118.9 |
C14—C15—H15 | 120.0 | C37—C38—H38 | 118.9 |
C15—C16—C17 | 121.3 (11) | | |
| | | |
O2—C1—C2—N | 7.8 (12) | O23—C22—C23—C28 | 112.7 (11) |
O1—C1—C2—N | −168.9 (8) | C21—C22—C23—C28 | −129.3 (10) |
O2—C1—C2—C3 | −116.7 (10) | O23—C22—C23—C24 | −71.3 (12) |
O1—C1—C2—C3 | 66.6 (11) | C21—C22—C23—C24 | 46.7 (13) |
N—C2—C3—C4 | −66.6 (12) | C28—C23—C24—C25 | −3.0 (17) |
C1—C2—C3—C4 | 53.4 (12) | C22—C23—C24—C25 | −179.0 (11) |
C2—C3—C4—S | −177.8 (8) | C23—C24—C25—C26 | 0.2 (19) |
C5—S—C4—C3 | −174.9 (8) | C24—C25—C26—C27 | 2 (2) |
O12—C11—C12—O13 | 13.7 (12) | C25—C26—C27—C28 | −1.8 (19) |
O11—C11—C12—O13 | −166.5 (7) | C24—C23—C28—C27 | 3.4 (17) |
O12—C11—C12—C13 | −106.9 (10) | C22—C23—C28—C27 | 179.4 (11) |
O11—C11—C12—C13 | 72.9 (10) | C26—C27—C28—C23 | −1.1 (18) |
O13—C12—C13—C14 | 135.8 (10) | O31—C31—C32—O33 | 12.5 (12) |
C11—C12—C13—C14 | −103.4 (12) | O32—C31—C32—O33 | −158.9 (8) |
O13—C12—C13—C18 | −45.5 (15) | O31—C31—C32—C33 | −107.9 (11) |
C11—C12—C13—C18 | 75.2 (13) | O32—C31—C32—C33 | 80.8 (12) |
C18—C13—C14—C15 | −2.8 (18) | O33—C32—C33—C38 | −11.8 (14) |
C12—C13—C14—C15 | 175.9 (11) | C31—C32—C33—C38 | 108.6 (13) |
C13—C14—C15—C16 | 5 (2) | O33—C32—C33—C34 | 166.3 (10) |
C14—C15—C16—C17 | −5 (2) | C31—C32—C33—C34 | −73.3 (14) |
C15—C16—C17—C18 | 3 (2) | C38—C33—C34—C35 | −3.2 (19) |
C16—C17—C18—C13 | −1 (2) | C32—C33—C34—C35 | 178.6 (12) |
C14—C13—C18—C17 | 1.0 (19) | C33—C34—C35—C36 | 3 (2) |
C12—C13—C18—C17 | −177.7 (12) | C34—C35—C36—C37 | −1 (2) |
O22—C21—C22—O23 | 5.9 (12) | C35—C36—C37—C38 | −1 (2) |
O21—C21—C22—O23 | −172.7 (7) | C34—C33—C38—C37 | 0.9 (18) |
O22—C21—C22—C23 | −116.6 (10) | C32—C33—C38—C37 | 179.1 (11) |
O21—C21—C22—C23 | 64.7 (11) | C36—C37—C38—C33 | 1.2 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O22i | 0.96 | 1.80 | 2.751 (10) | 170 |
O11—H11···O32ii | 0.95 | 1.66 | 2.495 (10) | 144 |
O13—H13···O23iii | 0.87 | 2.11 | 2.978 (8) | 179 |
O21—H21···O12iv | 1.00 | 1.67 | 2.640 (10) | 163 |
O23—H23···O32v | 0.87 | 2.02 | 2.679 (10) | 131 |
O33—H33···O13 | 0.96 | 2.10 | 2.921 (11) | 142 |
N—H1A···O31i | 0.89 | 2.10 | 2.973 (9) | 168 |
N—H1B···O23 | 0.89 | 2.06 | 2.924 (11) | 164 |
N—H1C···O33 | 0.89 | 1.96 | 2.833 (10) | 166 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x+1, y, z; (iii) −x+1, y+1/2, −z+1/2; (iv) x−1, y, z; (v) x, y−1, z. |
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