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research communications
of canagliflozin hemihydrate
aChemistry Department, Zhejiang University, Hangzhou, Zhejiang 310028, People's Republic of China, and bCenter of Analysis and Measurement, Zhejiang University, Hangzhou, Zhejiang 310028, People's Republic of China
*Correspondence e-mail: huxiurong@zju.edu.cn
There are two canagliflozin molecules (A and B) and one water molecule in the of the title compound, C24H25FO5S·0.5H2O [systematic name: (2S,3R,4R,5S,6R)-2-(3-{[5-(4-fluorophenyl)thiophen-2-yl]methyl}-4-methylphenyl)-6-(hydroxymethyl)-3,4,5,6-tetrahydro-2H-pyran-3,4,5-triol hemihydrate]. The dihedral angles between the methylbenzene and thiophene rings are 115.7 (4) and 111.7 (4)°, while the dihedral angles between the fluorobenzene and thiophene rings are 24.2 (6) and 20.5 (9)° in molecules A and B, respectively. The hydropyran ring exhibits a chair conformation in both canagliflozin molecules. In the crystal, the canagliflozin molecules and lattice water molecules are connected via O—H⋯O hydrogen bonds into a three-dimensional supramolecular architecture.
Keywords: crystal structure; canagliflozin; hydrogen bonding.
CCDC reference: 1475516
1. Chemical context
Canagliflozin is a member of a new class of anti-diabetic drugs which are used to improve glycemic control of diabetics (Cefalu et al., 2013). The crystalline forms of canagliflozin have been reported (Mitsubishi et al., 2013
; Ahmed et al., 2013
; Chen et al., 2013
), we report here the single-crystal structure of the title compound.
2. Structural commentary
The title compound crystallizes with two independent canagliflozin molecules and one water molecule in the ). The water molecule links the two canagliflozin molecules (A and B) via two O—H⋯O hydrogen bonds (Table 1
).
|
![]() | Figure 1 The molecular structure of the title compound, (I) ![]() |
The conformations of the two canagliflozin molecules are somewhat different with regard to the orientation of the central benzene ring (C12–C17) with respect to the thiophene ring, as indicated by torsion angles C9A—C10A—C11A—C12A = 113.3 (6)° in molecule A and C9B—C10B—C11B—C12B = 108.0 (6)° in molecule B. The conformational difference is also shown by the angle C10—C11—C12, which is 115.7 (4)° in molecule A and 111.7 (4)° in molecule B. The terminal aromatic rings (C1–C6) are inclined to the thiophene rings, forming dihedral angles of 24.2 (6) and 20.5 (9)° in molecules A and B, respectively. The tetrahydropyran rings exhibit a distorted chair conformation in both molecules A and B.
3. Supramolecular features
In the crystal, O3B—H3B1⋯O4Bi, O2B–H2B1⋯O4Aiii, and O5B—H5B1⋯O3Biv [symmetry code: (i) x − , −y +
, −z + 1; (iii) x, y + 1, z; (iv) x + 1, y, z] link canagliflozin molecules, generating a ring of graph-set motif R33(9). The presence of the water molecules results in the formation of zigzag chains mediated by alternating O4B—H4B⋯O6, O6—H61⋯O2A and O4A—H4A⋯O5Bii [symmetry code: (ii) x − 1, y − 1, z] hydrogen bonds propagating along the a axis; the chains are stacked along the c axis by further hydrogen-bonding interactions, O3A—H3A1⋯O2Bi and O2A–-H2A1⋯O2Bi (Fig. 2
).
![]() | Figure 2 Part of the crystal packing of the title compound, showing the extensive intermolecular hydrogen-bonding interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity. |
4. Synthesis and crystallization
The crude product was supplied by Zhejiang Huadong Pharmaceutical Co., Ltd. It was recrystallized from methanol solution, giving colorless crystals suitable for X-ray diffraction.
5. Refinement
Crystal data, data collection and structure . All H atoms were placed in calculated positions with C—H = 0.93–0.98 Å and O—H = 0.82 Å and included in the using a riding model, with Uiso(H) = 1.2Ueq or 1.5Ueq(carrier atom).
|
Supporting information
CCDC reference: 1475516
10.1107/S2056989016006769/xu5886sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989016006769/xu5886Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989016006769/xu5886Isup3.cml
Canagliflozin is a member of a new class of anti-diabetic drugs which are used to improve glycemic control of diabetics (Cefalu et al., 2013). The crystalline forms of canagliflozin have been reported (Mitsubishi et al., 2013; Ahmed et al., 2013; Chen et al., 2013), we report here the single-crystal structure of the title compound.
The title compound crystallizes with two independent canagliflozin molecules and one water molecule in the
(Fig. 1). The water molecule links the two independent canagliflozin molecule (A and B) via two O—H···O hydrogen bonds (Table 1).The conformations of the two canagliflozin molecules are somewhat different with regard to the orientation of the central benzene ring (C12–C17) with respect to the thiophene ring, as indicated by torsion angles C9A—C10A—C11A—C12A = 113.3 (6)° in molecule A and C9B—C10B—C11B—C12B = 108.0 (6)° in molecule B. The conformational difference is also shown by the angle C10—C11—C12, which is 115.7 (4)° in molecule A and 111.7 (4)° in molecule B. The terminal aromatic rings (C1–C6) are inclined to the thiophene rings, forming dihedral angles of 24.2 (6) and 20.5 (9)° in molecules A and B, respectively. The tetrahydropyran rings exhibit a distorted chair conformation in both molecules A and B.
In the crystal, O3B—H3B1···O4Bi, O2B–H2B1···O4Aiii, and O5B—H5B1···O3Biv [symmetry code: (i) x - 1/2, -y + 3/2, -z + 1; (iii) x, y + 1, z; (iv) x + 1, y, z] link canagliflozin molecules, generating a ring of graph-set motif R33(9). The presence of the water molecules results in the formation of zigzag chains mediated by alternating O4B—H4B···O6, O6—H61···O2A and O4A—H4A···O5Bii [symmetry code: (ii) x - 1, y - 1, z] hydrogen bonds propagating along the a axis; the chains are stacked along the c axis by further hydrogen-bonding interactions, O3A—H3A1···O2Bi and O2A–-H2A1···O2Bi (Fig. 2).
The crude product was supplied by Zhejiang Huadong Pharmaceutical Co., Ltd. It was recrystallized from methanol solution, giving colorless crystals suitable for X-ray diffraction.
Canagliflozin is a member of a new class of anti-diabetic drugs which are used to improve glycemic control of diabetics (Cefalu et al., 2013). The crystalline forms of canagliflozin have been reported (Mitsubishi et al., 2013; Ahmed et al., 2013; Chen et al., 2013), we report here the single-crystal structure of the title compound.
The title compound crystallizes with two independent canagliflozin molecules and one water molecule in the
(Fig. 1). The water molecule links the two independent canagliflozin molecule (A and B) via two O—H···O hydrogen bonds (Table 1).The conformations of the two canagliflozin molecules are somewhat different with regard to the orientation of the central benzene ring (C12–C17) with respect to the thiophene ring, as indicated by torsion angles C9A—C10A—C11A—C12A = 113.3 (6)° in molecule A and C9B—C10B—C11B—C12B = 108.0 (6)° in molecule B. The conformational difference is also shown by the angle C10—C11—C12, which is 115.7 (4)° in molecule A and 111.7 (4)° in molecule B. The terminal aromatic rings (C1–C6) are inclined to the thiophene rings, forming dihedral angles of 24.2 (6) and 20.5 (9)° in molecules A and B, respectively. The tetrahydropyran rings exhibit a distorted chair conformation in both molecules A and B.
In the crystal, O3B—H3B1···O4Bi, O2B–H2B1···O4Aiii, and O5B—H5B1···O3Biv [symmetry code: (i) x - 1/2, -y + 3/2, -z + 1; (iii) x, y + 1, z; (iv) x + 1, y, z] link canagliflozin molecules, generating a ring of graph-set motif R33(9). The presence of the water molecules results in the formation of zigzag chains mediated by alternating O4B—H4B···O6, O6—H61···O2A and O4A—H4A···O5Bii [symmetry code: (ii) x - 1, y - 1, z] hydrogen bonds propagating along the a axis; the chains are stacked along the c axis by further hydrogen-bonding interactions, O3A—H3A1···O2Bi and O2A–-H2A1···O2Bi (Fig. 2).
The crude product was supplied by Zhejiang Huadong Pharmaceutical Co., Ltd. It was recrystallized from methanol solution, giving colorless crystals suitable for X-ray diffraction.
detailsCrystal data, data collection and structure
details are summarized in Table 2. All H atoms were placed in calculated positions with C—H = 0.93–0.98 Å and O—H = 0.82 Å and included in the using a riding model, with Uiso(H) = 1.2Ueq or 1.5Ueq(carrier atom).Data collection: PROCESS-AUTO (Rigaku, 2006); cell
PROCESS-AUTO (Rigaku, 2006); data reduction: CrystalStructure (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 2012).2C24H25FO5S·H2O | F(000) = 1912 |
Mr = 907.02 | Dx = 1.369 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 23292 reflections |
a = 8.4259 (4) Å | θ = 3.0–27.4° |
b = 11.4264 (7) Å | µ = 0.19 mm−1 |
c = 45.706 (2) Å | T = 296 K |
V = 4400.4 (4) Å3 | Needle, colorless |
Z = 4 | 0.48 × 0.28 × 0.26 mm |
Rigaku R-AXIS RAPID diffractometer | 9958 independent reflections |
Radiation source: rotating anode | 5079 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.145 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −14→14 |
Tmin = 0.914, Tmax = 0.952 | l = −59→59 |
43211 measured reflections |
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)] = 0.080 | H-atom parameters constrained |
wR(F2) = 0.147 | w = 1/[σ2(Fo2) + (0.0408P)2 + 2.8647P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
9958 reflections | Δρmax = 0.38 e Å−3 |
575 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 3246 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.13 (11) |
2C24H25FO5S·H2O | V = 4400.4 (4) Å3 |
Mr = 907.02 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.4259 (4) Å | µ = 0.19 mm−1 |
b = 11.4264 (7) Å | T = 296 K |
c = 45.706 (2) Å | 0.48 × 0.28 × 0.26 mm |
Rigaku R-AXIS RAPID diffractometer | 9958 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 5079 reflections with I > 2σ(I) |
Tmin = 0.914, Tmax = 0.952 | Rint = 0.145 |
43211 measured reflections |
R[F2 > 2σ(F2)] = 0.080 | H-atom parameters constrained |
wR(F2) = 0.147 | Δρmax = 0.38 e Å−3 |
S = 1.00 | Δρmin = −0.29 e Å−3 |
9958 reflections | Absolute structure: Flack (1983), 3246 Friedel pairs |
575 parameters | Absolute structure parameter: 0.13 (11) |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
C1A | 0.8230 (6) | 0.7018 (5) | 0.29229 (10) | 0.0474 (13) | |
C2A | 0.9098 (7) | 0.7759 (5) | 0.27372 (11) | 0.0595 (16) | |
H2A | 0.8808 | 0.8542 | 0.2721 | 0.071* | |
C3A | 1.0373 (7) | 0.7347 (6) | 0.25788 (12) | 0.0692 (17) | |
H3A | 1.0956 | 0.7843 | 0.2458 | 0.083* | |
C4A | 1.0755 (7) | 0.6195 (7) | 0.26042 (13) | 0.0676 (18) | |
C5A | 0.9969 (7) | 0.5431 (5) | 0.27796 (12) | 0.0652 (16) | |
H5A | 1.0277 | 0.4651 | 0.2793 | 0.078* | |
C6A | 0.8699 (7) | 0.5855 (5) | 0.29361 (11) | 0.0601 (15) | |
H6A | 0.8134 | 0.5343 | 0.3055 | 0.072* | |
C7A | 0.6928 (6) | 0.7483 (5) | 0.31027 (9) | 0.0451 (12) | |
C8A | 0.6052 (6) | 0.8464 (5) | 0.30734 (11) | 0.0554 (15) | |
H8A | 0.6133 | 0.8964 | 0.2914 | 0.066* | |
C9A | 0.4994 (6) | 0.8657 (5) | 0.33098 (12) | 0.0557 (15) | |
H9A | 0.4306 | 0.9293 | 0.3318 | 0.067* | |
C10A | 0.5076 (6) | 0.7834 (4) | 0.35224 (10) | 0.0421 (12) | |
C11A | 0.4200 (6) | 0.7753 (4) | 0.38050 (10) | 0.0477 (13) | |
H11A | 0.3621 | 0.8478 | 0.3834 | 0.057* | |
H11B | 0.4969 | 0.7688 | 0.3962 | 0.057* | |
C12A | 0.3033 (5) | 0.6737 (4) | 0.38309 (9) | 0.0369 (11) | |
C13A | 0.3383 (5) | 0.5781 (4) | 0.40050 (9) | 0.0343 (11) | |
H13A | 0.4332 | 0.5779 | 0.4109 | 0.041* | |
C14A | 0.2385 (5) | 0.4834 (4) | 0.40311 (9) | 0.0369 (11) | |
C15A | 0.0979 (5) | 0.4846 (4) | 0.38708 (10) | 0.0404 (12) | |
H15A | 0.0283 | 0.4216 | 0.3883 | 0.049* | |
C16A | 0.0611 (6) | 0.5791 (5) | 0.36942 (10) | 0.0482 (13) | |
H16A | −0.0332 | 0.5784 | 0.3588 | 0.058* | |
C17A | 0.1607 (6) | 0.6745 (5) | 0.36711 (10) | 0.0463 (12) | |
C18A | 0.1135 (7) | 0.7778 (5) | 0.34833 (12) | 0.0690 (17) | |
H18A | 0.0041 | 0.7703 | 0.3428 | 0.104* | |
H18B | 0.1787 | 0.7798 | 0.3311 | 0.104* | |
H18C | 0.1278 | 0.8489 | 0.3592 | 0.104* | |
C19A | 0.2741 (5) | 0.3786 (4) | 0.42179 (9) | 0.0357 (11) | |
H19A | 0.3865 | 0.3797 | 0.4273 | 0.043* | |
C20A | 0.1737 (5) | 0.3719 (4) | 0.44938 (9) | 0.0326 (11) | |
H20A | 0.0615 | 0.3757 | 0.4438 | 0.039* | |
C21A | 0.2017 (5) | 0.2584 (4) | 0.46571 (8) | 0.0339 (10) | |
H21A | 0.3096 | 0.2591 | 0.4737 | 0.041* | |
C22A | 0.1845 (5) | 0.1543 (4) | 0.44575 (9) | 0.0340 (11) | |
H22A | 0.0726 | 0.1443 | 0.4405 | 0.041* | |
C23A | 0.2830 (6) | 0.1693 (4) | 0.41808 (9) | 0.0424 (12) | |
H23A | 0.3968 | 0.1644 | 0.4223 | 0.051* | |
C24A | 0.2307 (7) | 0.0731 (5) | 0.39562 (10) | 0.0588 (13) | |
H24A | 0.2386 | −0.0039 | 0.4045 | 0.071* | |
H24B | 0.1215 | 0.0858 | 0.3897 | 0.071* | |
C1B | 1.2588 (6) | 1.2409 (5) | 0.30205 (11) | 0.0562 (14) | |
C2B | 1.3509 (7) | 1.1863 (6) | 0.28096 (13) | 0.0768 (19) | |
H2B | 1.3240 | 1.1110 | 0.2751 | 0.092* | |
C3B | 1.4806 (7) | 1.2395 (8) | 0.26844 (14) | 0.085 (2) | |
H3B | 1.5430 | 1.2007 | 0.2548 | 0.102* | |
C4B | 1.5136 (8) | 1.3496 (8) | 0.27672 (16) | 0.085 (2) | |
C5B | 1.4341 (8) | 1.4082 (7) | 0.29795 (16) | 0.086 (2) | |
H5B | 1.4656 | 1.4824 | 0.3039 | 0.103* | |
C6B | 1.3035 (7) | 1.3528 (6) | 0.31044 (13) | 0.0697 (17) | |
H6B | 1.2451 | 1.3917 | 0.3247 | 0.084* | |
C7B | 1.1148 (6) | 1.1843 (5) | 0.31376 (10) | 0.0499 (13) | |
C8B | 1.0747 (7) | 1.0717 (6) | 0.31352 (12) | 0.0637 (16) | |
H8B | 1.1397 | 1.0133 | 0.3060 | 0.076* | |
C9B | 0.9242 (7) | 1.0495 (5) | 0.32585 (12) | 0.0627 (16) | |
H9B | 0.8806 | 0.9750 | 0.3274 | 0.075* | |
C10B | 0.8499 (6) | 1.1468 (5) | 0.33522 (9) | 0.0441 (13) | |
C11B | 0.6910 (6) | 1.1544 (5) | 0.35001 (10) | 0.0532 (14) | |
H11C | 0.6363 | 1.0801 | 0.3480 | 0.064* | |
H11D | 0.6274 | 1.2139 | 0.3404 | 0.064* | |
C12B | 0.7072 (5) | 1.1844 (5) | 0.38244 (9) | 0.0389 (12) | |
C13B | 0.7355 (5) | 1.0932 (4) | 0.40164 (9) | 0.0355 (11) | |
H13B | 0.7394 | 1.0170 | 0.3945 | 0.043* | |
C14B | 0.7583 (5) | 1.1132 (4) | 0.43165 (9) | 0.0334 (11) | |
C15B | 0.7535 (5) | 1.2272 (4) | 0.44152 (10) | 0.0373 (11) | |
H15B | 0.7706 | 1.2431 | 0.4612 | 0.045* | |
C16B | 0.7237 (5) | 1.3172 (4) | 0.42246 (10) | 0.0437 (12) | |
H16B | 0.7195 | 1.3933 | 0.4296 | 0.052* | |
C17B | 0.6997 (5) | 1.2985 (4) | 0.39290 (11) | 0.0411 (12) | |
C18B | 0.6624 (6) | 1.4007 (5) | 0.37319 (11) | 0.0586 (15) | |
H18D | 0.6825 | 1.4725 | 0.3835 | 0.088* | |
H18E | 0.5528 | 1.3977 | 0.3675 | 0.088* | |
H18F | 0.7281 | 1.3971 | 0.3561 | 0.088* | |
C19B | 0.7807 (5) | 1.0121 (4) | 0.45231 (9) | 0.0330 (10) | |
H19B | 0.8318 | 1.0399 | 0.4703 | 0.040* | |
C20B | 0.6217 (5) | 0.9556 (4) | 0.45993 (9) | 0.0302 (10) | |
H20B | 0.5595 | 0.9465 | 0.4420 | 0.036* | |
C21B | 0.6378 (5) | 0.8365 (4) | 0.47464 (9) | 0.0353 (11) | |
H21B | 0.6707 | 0.8489 | 0.4950 | 0.042* | |
C22B | 0.7590 (5) | 0.7601 (4) | 0.46008 (9) | 0.0341 (10) | |
H22B | 0.7200 | 0.7347 | 0.4409 | 0.041* | |
C23B | 0.9139 (5) | 0.8280 (4) | 0.45649 (9) | 0.0335 (11) | |
H23B | 0.9519 | 0.8539 | 0.4757 | 0.040* | |
C24B | 1.0424 (5) | 0.7610 (4) | 0.44114 (10) | 0.0466 (12) | |
H24C | 1.0593 | 0.6864 | 0.4508 | 0.056* | |
H24D | 1.0119 | 0.7461 | 0.4210 | 0.056* | |
F1A | 1.2033 (4) | 0.5781 (4) | 0.24514 (8) | 0.0935 (12) | |
F1B | 1.6394 (5) | 1.4058 (5) | 0.26352 (10) | 0.1351 (18) | |
O1A | 0.2438 (4) | 0.2775 (3) | 0.40429 (6) | 0.0421 (8) | |
O2A | 0.2095 (4) | 0.4714 (3) | 0.46711 (6) | 0.0440 (8) | |
H2A1 | 0.2400 | 0.4495 | 0.4832 | 0.066* | |
O3A | 0.0913 (4) | 0.2435 (3) | 0.48929 (6) | 0.0441 (8) | |
H3A1 | 0.0983 | 0.2991 | 0.5006 | 0.066* | |
O4A | 0.2376 (4) | 0.0535 (3) | 0.46192 (7) | 0.0406 (8) | |
H4A | 0.1973 | −0.0057 | 0.4550 | 0.061* | |
O5A | 0.3311 (6) | 0.0803 (4) | 0.37124 (10) | 0.0913 (14) | |
H5A1 | 0.3019 | 0.1340 | 0.3606 | 0.137* | |
O1B | 0.8812 (3) | 0.9285 (3) | 0.43833 (6) | 0.0370 (7) | |
O2B | 0.5393 (3) | 1.0343 (3) | 0.47925 (6) | 0.0371 (8) | |
H2B1 | 0.4465 | 1.0401 | 0.4741 | 0.056* | |
O3B | 0.4879 (4) | 0.7782 (3) | 0.47478 (7) | 0.0472 (8) | |
H3B1 | 0.4316 | 0.8062 | 0.4876 | 0.071* | |
O4B | 0.7951 (4) | 0.6600 (3) | 0.47784 (7) | 0.0463 (8) | |
H4B | 0.7223 | 0.6126 | 0.4768 | 0.069* | |
O5B | 1.1853 (4) | 0.8292 (3) | 0.44195 (8) | 0.0559 (9) | |
H5B1 | 1.2601 | 0.7872 | 0.4466 | 0.084* | |
O6 | 0.5619 (4) | 0.4920 (3) | 0.47940 (8) | 0.0602 (10) | |
H61 | 0.4711 | 0.4818 | 0.4733 | 0.090* | |
H62 | 0.5714 | 0.4204 | 0.4819 | 0.090* | |
S1A | 0.64414 (16) | 0.67821 (12) | 0.34263 (3) | 0.0523 (4) | |
S1B | 0.96635 (17) | 1.26679 (13) | 0.32902 (3) | 0.0598 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.055 (3) | 0.047 (4) | 0.041 (3) | −0.002 (3) | −0.004 (3) | 0.002 (2) |
C2A | 0.067 (4) | 0.057 (4) | 0.054 (3) | −0.010 (3) | −0.002 (3) | 0.010 (3) |
C3A | 0.063 (4) | 0.085 (5) | 0.060 (4) | 0.000 (4) | 0.014 (3) | 0.011 (4) |
C4A | 0.060 (4) | 0.083 (5) | 0.060 (4) | −0.005 (4) | 0.005 (3) | −0.011 (4) |
C5A | 0.077 (4) | 0.057 (4) | 0.062 (4) | 0.005 (4) | 0.010 (4) | −0.002 (3) |
C6A | 0.071 (4) | 0.049 (4) | 0.060 (3) | −0.009 (3) | 0.009 (3) | 0.006 (3) |
C7A | 0.052 (3) | 0.039 (3) | 0.044 (3) | −0.014 (3) | 0.000 (2) | 0.013 (3) |
C8A | 0.066 (4) | 0.045 (4) | 0.055 (3) | 0.006 (3) | 0.010 (3) | 0.017 (3) |
C9A | 0.062 (4) | 0.035 (3) | 0.070 (4) | 0.007 (3) | 0.003 (3) | 0.009 (3) |
C10A | 0.047 (3) | 0.032 (3) | 0.048 (3) | 0.005 (2) | 0.006 (2) | 0.008 (2) |
C11A | 0.061 (3) | 0.030 (3) | 0.052 (3) | −0.002 (3) | 0.005 (3) | 0.000 (2) |
C12A | 0.047 (3) | 0.025 (3) | 0.038 (2) | −0.004 (2) | 0.008 (2) | −0.005 (2) |
C13A | 0.033 (3) | 0.035 (3) | 0.035 (2) | −0.001 (2) | 0.001 (2) | −0.004 (2) |
C14A | 0.042 (3) | 0.033 (3) | 0.036 (2) | 0.002 (2) | 0.004 (2) | 0.000 (2) |
C15A | 0.042 (3) | 0.031 (3) | 0.048 (3) | −0.003 (2) | −0.009 (2) | 0.003 (2) |
C16A | 0.045 (3) | 0.047 (3) | 0.053 (3) | −0.004 (3) | −0.013 (3) | 0.010 (3) |
C17A | 0.055 (3) | 0.042 (3) | 0.042 (3) | 0.002 (3) | −0.005 (3) | 0.005 (2) |
C18A | 0.074 (4) | 0.050 (4) | 0.083 (4) | −0.001 (3) | −0.020 (3) | 0.021 (3) |
C19A | 0.034 (3) | 0.029 (3) | 0.044 (3) | 0.000 (2) | 0.002 (2) | 0.002 (2) |
C20A | 0.037 (3) | 0.023 (3) | 0.038 (2) | −0.002 (2) | 0.000 (2) | −0.001 (2) |
C21A | 0.033 (2) | 0.033 (3) | 0.036 (2) | −0.003 (2) | −0.004 (2) | 0.003 (2) |
C22A | 0.033 (2) | 0.024 (3) | 0.045 (3) | 0.002 (2) | −0.005 (2) | 0.002 (2) |
C23A | 0.049 (3) | 0.037 (3) | 0.042 (3) | 0.010 (3) | −0.003 (2) | −0.002 (2) |
C24A | 0.086 | 0.044 (3) | 0.046 (3) | 0.026 (3) | 0.038 (3) | 0.008 (3) |
C1B | 0.058 (3) | 0.063 (4) | 0.047 (3) | 0.017 (3) | −0.003 (3) | 0.002 (3) |
C2B | 0.062 (4) | 0.089 (5) | 0.079 (4) | 0.006 (4) | 0.001 (4) | −0.013 (4) |
C3B | 0.056 (4) | 0.116 (7) | 0.082 (5) | 0.004 (5) | 0.012 (4) | −0.016 (5) |
C4B | 0.051 (4) | 0.116 (7) | 0.088 (5) | −0.020 (4) | 0.008 (4) | 0.000 (5) |
C5B | 0.070 (5) | 0.090 (6) | 0.098 (5) | −0.013 (4) | 0.001 (4) | −0.001 (5) |
C6B | 0.064 (4) | 0.078 (5) | 0.068 (4) | 0.006 (4) | 0.009 (3) | −0.007 (3) |
C7B | 0.048 (3) | 0.056 (4) | 0.046 (3) | 0.008 (3) | 0.003 (3) | −0.006 (3) |
C8B | 0.062 (4) | 0.056 (4) | 0.073 (4) | 0.016 (3) | 0.002 (3) | −0.003 (3) |
C9B | 0.075 (4) | 0.049 (4) | 0.064 (4) | −0.006 (3) | −0.012 (3) | 0.004 (3) |
C10B | 0.058 (3) | 0.043 (3) | 0.032 (3) | −0.014 (3) | 0.000 (2) | 0.009 (2) |
C11B | 0.057 (3) | 0.058 (4) | 0.045 (3) | −0.006 (3) | −0.002 (3) | 0.011 (3) |
C12B | 0.031 (2) | 0.051 (3) | 0.035 (2) | −0.003 (2) | −0.004 (2) | 0.007 (2) |
C13B | 0.040 (3) | 0.033 (3) | 0.034 (2) | −0.002 (2) | 0.002 (2) | 0.005 (2) |
C14B | 0.028 (2) | 0.029 (3) | 0.043 (3) | 0.003 (2) | 0.003 (2) | 0.009 (2) |
C15B | 0.036 (2) | 0.034 (3) | 0.042 (2) | 0.002 (2) | 0.004 (2) | 0.006 (2) |
C16B | 0.040 (3) | 0.032 (3) | 0.059 (3) | 0.002 (2) | 0.013 (3) | 0.008 (3) |
C17B | 0.033 (3) | 0.038 (3) | 0.052 (3) | 0.006 (2) | 0.007 (2) | 0.018 (2) |
C18B | 0.055 (3) | 0.050 (4) | 0.070 (4) | 0.014 (3) | 0.005 (3) | 0.026 (3) |
C19B | 0.037 (3) | 0.028 (3) | 0.034 (2) | 0.006 (2) | 0.001 (2) | 0.002 (2) |
C20B | 0.030 (2) | 0.031 (3) | 0.029 (2) | 0.001 (2) | 0.000 (2) | −0.0001 (19) |
C21B | 0.034 (2) | 0.034 (3) | 0.038 (2) | −0.005 (2) | 0.000 (2) | 0.004 (2) |
C22B | 0.038 (3) | 0.023 (3) | 0.041 (2) | −0.002 (2) | −0.007 (2) | 0.005 (2) |
C23B | 0.040 (3) | 0.022 (2) | 0.038 (2) | 0.011 (2) | 0.000 (2) | −0.001 (2) |
C24B | 0.045 (3) | 0.038 (3) | 0.056 (3) | 0.004 (3) | 0.003 (2) | 0.006 (3) |
F1A | 0.074 (2) | 0.115 (3) | 0.091 (2) | 0.010 (2) | 0.028 (2) | −0.011 (2) |
F1B | 0.076 (3) | 0.183 (5) | 0.146 (4) | −0.037 (3) | 0.029 (3) | −0.007 (4) |
O1A | 0.056 (2) | 0.0316 (19) | 0.0392 (16) | 0.0070 (17) | 0.0008 (15) | 0.0012 (15) |
O2A | 0.061 (2) | 0.031 (2) | 0.0395 (17) | −0.0058 (17) | −0.0058 (17) | −0.0042 (15) |
O3A | 0.057 (2) | 0.039 (2) | 0.0357 (17) | −0.0041 (18) | 0.0126 (15) | 0.0011 (16) |
O4A | 0.045 (2) | 0.0237 (18) | 0.0527 (19) | −0.0026 (16) | −0.0045 (16) | 0.0017 (15) |
O5A | 0.101 (4) | 0.085 (4) | 0.088 (3) | 0.020 (3) | 0.006 (3) | −0.006 (3) |
O1B | 0.0411 (17) | 0.0312 (19) | 0.0388 (16) | 0.0069 (15) | 0.0085 (15) | 0.0103 (15) |
O2B | 0.0341 (16) | 0.037 (2) | 0.0405 (17) | 0.0026 (15) | 0.0010 (15) | −0.0046 (15) |
O3B | 0.0437 (19) | 0.040 (2) | 0.058 (2) | −0.0110 (17) | 0.0070 (16) | 0.0015 (16) |
O4B | 0.047 (2) | 0.0264 (19) | 0.066 (2) | −0.0040 (16) | −0.0110 (18) | 0.0141 (17) |
O5B | 0.042 (2) | 0.042 (2) | 0.084 (3) | 0.0068 (18) | 0.009 (2) | −0.002 (2) |
O6 | 0.062 (2) | 0.041 (2) | 0.079 (3) | −0.0114 (19) | −0.011 (2) | 0.007 (2) |
S1A | 0.0602 (8) | 0.0419 (8) | 0.0549 (8) | 0.0073 (7) | 0.0109 (7) | 0.0161 (7) |
S1B | 0.0673 (9) | 0.0499 (10) | 0.0621 (8) | −0.0040 (8) | 0.0172 (7) | −0.0030 (7) |
C1A—C6A | 1.387 (7) | C3B—C4B | 1.344 (9) |
C1A—C2A | 1.405 (7) | C3B—H3B | 0.9300 |
C1A—C7A | 1.470 (7) | C4B—C5B | 1.356 (9) |
C2A—C3A | 1.378 (8) | C4B—F1B | 1.378 (7) |
C2A—H2A | 0.9300 | C5B—C6B | 1.391 (8) |
C3A—C4A | 1.360 (8) | C5B—H5B | 0.9300 |
C3A—H3A | 0.9300 | C6B—H6B | 0.9300 |
C4A—C5A | 1.358 (8) | C7B—C8B | 1.330 (8) |
C4A—F1A | 1.368 (7) | C7B—S1B | 1.715 (5) |
C5A—C6A | 1.376 (8) | C8B—C9B | 1.411 (8) |
C5A—H5A | 0.9300 | C8B—H8B | 0.9300 |
C6A—H6A | 0.9300 | C9B—C10B | 1.345 (7) |
C7A—C8A | 1.348 (7) | C9B—H9B | 0.9300 |
C7A—S1A | 1.731 (4) | C10B—C11B | 1.502 (7) |
C8A—C9A | 1.418 (7) | C10B—S1B | 1.710 (5) |
C8A—H8A | 0.9300 | C11B—C12B | 1.527 (6) |
C9A—C10A | 1.354 (6) | C11B—H11C | 0.9700 |
C9A—H9A | 0.9300 | C11B—H11D | 0.9700 |
C10A—C11A | 1.491 (6) | C12B—C13B | 1.383 (6) |
C10A—S1A | 1.721 (5) | C12B—C17B | 1.390 (6) |
C11A—C12A | 1.526 (6) | C13B—C14B | 1.404 (6) |
C11A—H11A | 0.9700 | C13B—H13B | 0.9300 |
C11A—H11B | 0.9700 | C14B—C15B | 1.379 (6) |
C12A—C13A | 1.383 (6) | C14B—C19B | 1.504 (6) |
C12A—C17A | 1.407 (6) | C15B—C16B | 1.371 (6) |
C13A—C14A | 1.375 (6) | C15B—H15B | 0.9300 |
C13A—H13A | 0.9300 | C16B—C17B | 1.383 (6) |
C14A—C15A | 1.394 (6) | C16B—H16B | 0.9300 |
C14A—C19A | 1.501 (6) | C17B—C18B | 1.508 (6) |
C15A—C16A | 1.383 (6) | C18B—H18D | 0.9600 |
C15A—H15A | 0.9300 | C18B—H18E | 0.9600 |
C16A—C17A | 1.379 (7) | C18B—H18F | 0.9600 |
C16A—H16A | 0.9300 | C19B—O1B | 1.427 (5) |
C17A—C18A | 1.513 (7) | C19B—C20B | 1.528 (6) |
C18A—H18A | 0.9600 | C19B—H19B | 0.9800 |
C18A—H18B | 0.9600 | C20B—O2B | 1.439 (5) |
C18A—H18C | 0.9600 | C20B—C21B | 1.524 (6) |
C19A—O1A | 1.428 (5) | C20B—H20B | 0.9800 |
C19A—C20A | 1.521 (6) | C21B—O3B | 1.428 (5) |
C19A—H19A | 0.9800 | C21B—C22B | 1.499 (6) |
C20A—O2A | 1.428 (5) | C21B—H21B | 0.9800 |
C20A—C21A | 1.515 (6) | C22B—O4B | 1.436 (5) |
C20A—H20A | 0.9800 | C22B—C23B | 1.526 (6) |
C21A—O3A | 1.434 (5) | C22B—H22B | 0.9800 |
C21A—C22A | 1.506 (6) | C23B—O1B | 1.444 (5) |
C21A—H21A | 0.9800 | C23B—C24B | 1.500 (6) |
C22A—O4A | 1.439 (5) | C23B—H23B | 0.9800 |
C22A—C23A | 1.522 (6) | C24B—O5B | 1.435 (5) |
C22A—H22A | 0.9800 | C24B—H24C | 0.9700 |
C23A—O1A | 1.427 (5) | C24B—H24D | 0.9700 |
C23A—C24A | 1.567 (7) | O2A—H2A1 | 0.8200 |
C23A—H23A | 0.9800 | O3A—H3A1 | 0.8200 |
C24A—O5A | 1.401 (6) | O4A—H4A | 0.8200 |
C24A—H24A | 0.9700 | O5A—H5A1 | 0.8200 |
C24A—H24B | 0.9700 | O2B—H2B1 | 0.8200 |
C1B—C2B | 1.386 (7) | O3B—H3B1 | 0.8200 |
C1B—C6B | 1.387 (8) | O4B—H4B | 0.8200 |
C1B—C7B | 1.476 (7) | O5B—H5B1 | 0.8200 |
C2B—C3B | 1.375 (8) | O6—H61 | 0.8228 |
C2B—H2B | 0.9300 | O6—H62 | 0.8292 |
C6A—C1A—C2A | 117.1 (5) | C4B—C3B—H3B | 121.3 |
C6A—C1A—C7A | 122.3 (5) | C2B—C3B—H3B | 121.3 |
C2A—C1A—C7A | 120.5 (5) | C3B—C4B—C5B | 124.1 (7) |
C3A—C2A—C1A | 121.1 (6) | C3B—C4B—F1B | 118.2 (7) |
C3A—C2A—H2A | 119.4 | C5B—C4B—F1B | 117.7 (8) |
C1A—C2A—H2A | 119.4 | C4B—C5B—C6B | 117.4 (7) |
C4A—C3A—C2A | 118.0 (6) | C4B—C5B—H5B | 121.3 |
C4A—C3A—H3A | 121.0 | C6B—C5B—H5B | 121.3 |
C2A—C3A—H3A | 121.0 | C1B—C6B—C5B | 121.3 (6) |
C5A—C4A—C3A | 123.9 (6) | C1B—C6B—H6B | 119.3 |
C5A—C4A—F1A | 117.5 (6) | C5B—C6B—H6B | 119.3 |
C3A—C4A—F1A | 118.5 (6) | C8B—C7B—C1B | 129.0 (5) |
C4A—C5A—C6A | 117.4 (6) | C8B—C7B—S1B | 110.5 (4) |
C4A—C5A—H5A | 121.3 | C1B—C7B—S1B | 120.4 (4) |
C6A—C5A—H5A | 121.3 | C7B—C8B—C9B | 113.5 (6) |
C5A—C6A—C1A | 122.4 (5) | C7B—C8B—H8B | 123.3 |
C5A—C6A—H6A | 118.8 | C9B—C8B—H8B | 123.3 |
C1A—C6A—H6A | 118.8 | C10B—C9B—C8B | 113.4 (5) |
C8A—C7A—C1A | 130.8 (4) | C10B—C9B—H9B | 123.3 |
C8A—C7A—S1A | 109.9 (4) | C8B—C9B—H9B | 123.3 |
C1A—C7A—S1A | 119.1 (4) | C9B—C10B—C11B | 127.3 (5) |
C7A—C8A—C9A | 113.5 (5) | C9B—C10B—S1B | 110.0 (4) |
C7A—C8A—H8A | 123.3 | C11B—C10B—S1B | 122.6 (4) |
C9A—C8A—H8A | 123.3 | C10B—C11B—C12B | 111.7 (4) |
C10A—C9A—C8A | 114.0 (5) | C10B—C11B—H11C | 109.3 |
C10A—C9A—H9A | 123.0 | C12B—C11B—H11C | 109.3 |
C8A—C9A—H9A | 123.0 | C10B—C11B—H11D | 109.3 |
C9A—C10A—C11A | 129.8 (5) | C12B—C11B—H11D | 109.3 |
C9A—C10A—S1A | 109.6 (4) | H11C—C11B—H11D | 107.9 |
C11A—C10A—S1A | 120.6 (3) | C13B—C12B—C17B | 119.8 (4) |
C10A—C11A—C12A | 115.7 (4) | C13B—C12B—C11B | 117.5 (5) |
C10A—C11A—H11A | 108.4 | C17B—C12B—C11B | 122.7 (4) |
C12A—C11A—H11A | 108.4 | C12B—C13B—C14B | 121.4 (4) |
C10A—C11A—H11B | 108.4 | C12B—C13B—H13B | 119.3 |
C12A—C11A—H11B | 108.4 | C14B—C13B—H13B | 119.3 |
H11A—C11A—H11B | 107.4 | C15B—C14B—C13B | 118.0 (4) |
C13A—C12A—C17A | 119.1 (4) | C15B—C14B—C19B | 121.6 (4) |
C13A—C12A—C11A | 120.6 (4) | C13B—C14B—C19B | 120.4 (4) |
C17A—C12A—C11A | 120.3 (4) | C16B—C15B—C14B | 120.4 (4) |
C14A—C13A—C12A | 122.8 (4) | C16B—C15B—H15B | 119.8 |
C14A—C13A—H13A | 118.6 | C14B—C15B—H15B | 119.8 |
C12A—C13A—H13A | 118.6 | C15B—C16B—C17B | 122.1 (5) |
C13A—C14A—C15A | 117.8 (4) | C15B—C16B—H16B | 118.9 |
C13A—C14A—C19A | 123.7 (4) | C17B—C16B—H16B | 118.9 |
C15A—C14A—C19A | 118.5 (4) | C16B—C17B—C12B | 118.3 (4) |
C16A—C15A—C14A | 120.3 (5) | C16B—C17B—C18B | 119.6 (5) |
C16A—C15A—H15A | 119.8 | C12B—C17B—C18B | 122.0 (5) |
C14A—C15A—H15A | 119.8 | C17B—C18B—H18D | 109.5 |
C17A—C16A—C15A | 121.7 (5) | C17B—C18B—H18E | 109.5 |
C17A—C16A—H16A | 119.2 | H18D—C18B—H18E | 109.5 |
C15A—C16A—H16A | 119.2 | C17B—C18B—H18F | 109.5 |
C16A—C17A—C12A | 118.4 (5) | H18D—C18B—H18F | 109.5 |
C16A—C17A—C18A | 120.0 (4) | H18E—C18B—H18F | 109.5 |
C12A—C17A—C18A | 121.6 (5) | O1B—C19B—C14B | 107.9 (3) |
C17A—C18A—H18A | 109.5 | O1B—C19B—C20B | 109.9 (3) |
C17A—C18A—H18B | 109.5 | C14B—C19B—C20B | 110.9 (4) |
H18A—C18A—H18B | 109.5 | O1B—C19B—H19B | 109.4 |
C17A—C18A—H18C | 109.5 | C14B—C19B—H19B | 109.4 |
H18A—C18A—H18C | 109.5 | C20B—C19B—H19B | 109.4 |
H18B—C18A—H18C | 109.5 | O2B—C20B—C21B | 109.3 (3) |
O1A—C19A—C14A | 106.9 (3) | O2B—C20B—C19B | 107.4 (3) |
O1A—C19A—C20A | 109.0 (3) | C21B—C20B—C19B | 113.5 (3) |
C14A—C19A—C20A | 113.6 (4) | O2B—C20B—H20B | 108.8 |
O1A—C19A—H19A | 109.1 | C21B—C20B—H20B | 108.8 |
C14A—C19A—H19A | 109.1 | C19B—C20B—H20B | 108.8 |
C20A—C19A—H19A | 109.1 | O3B—C21B—C22B | 109.5 (4) |
O2A—C20A—C21A | 111.7 (3) | O3B—C21B—C20B | 109.8 (4) |
O2A—C20A—C19A | 108.2 (3) | C22B—C21B—C20B | 112.6 (3) |
C21A—C20A—C19A | 111.4 (4) | O3B—C21B—H21B | 108.3 |
O2A—C20A—H20A | 108.5 | C22B—C21B—H21B | 108.3 |
C21A—C20A—H20A | 108.5 | C20B—C21B—H21B | 108.3 |
C19A—C20A—H20A | 108.5 | O4B—C22B—C21B | 110.9 (3) |
O3A—C21A—C22A | 107.4 (4) | O4B—C22B—C23B | 106.5 (3) |
O3A—C21A—C20A | 111.7 (4) | C21B—C22B—C23B | 109.5 (4) |
C22A—C21A—C20A | 111.3 (3) | O4B—C22B—H22B | 109.9 |
O3A—C21A—H21A | 108.8 | C21B—C22B—H22B | 109.9 |
C22A—C21A—H21A | 108.8 | C23B—C22B—H22B | 109.9 |
C20A—C21A—H21A | 108.8 | O1B—C23B—C24B | 105.9 (3) |
O4A—C22A—C21A | 106.9 (3) | O1B—C23B—C22B | 107.6 (3) |
O4A—C22A—C23A | 110.3 (4) | C24B—C23B—C22B | 114.1 (4) |
C21A—C22A—C23A | 111.2 (4) | O1B—C23B—H23B | 109.7 |
O4A—C22A—H22A | 109.5 | C24B—C23B—H23B | 109.7 |
C21A—C22A—H22A | 109.5 | C22B—C23B—H23B | 109.7 |
C23A—C22A—H22A | 109.5 | O5B—C24B—C23B | 108.5 (4) |
O1A—C23A—C22A | 109.8 (4) | O5B—C24B—H24C | 110.0 |
O1A—C23A—C24A | 104.7 (3) | C23B—C24B—H24C | 110.0 |
C22A—C23A—C24A | 108.2 (4) | O5B—C24B—H24D | 110.0 |
O1A—C23A—H23A | 111.3 | C23B—C24B—H24D | 110.0 |
C22A—C23A—H23A | 111.3 | H24C—C24B—H24D | 108.4 |
C24A—C23A—H23A | 111.3 | C23A—O1A—C19A | 114.3 (3) |
O5A—C24A—C23A | 108.1 (5) | C20A—O2A—H2A1 | 109.5 |
O5A—C24A—H24A | 110.1 | C21A—O3A—H3A1 | 109.5 |
C23A—C24A—H24A | 110.1 | C22A—O4A—H4A | 109.5 |
O5A—C24A—H24B | 110.1 | C24A—O5A—H5A1 | 109.5 |
C23A—C24A—H24B | 110.1 | C19B—O1B—C23B | 112.8 (3) |
H24A—C24A—H24B | 108.4 | C20B—O2B—H2B1 | 109.5 |
C2B—C1B—C6B | 117.1 (6) | C21B—O3B—H3B1 | 109.5 |
C2B—C1B—C7B | 121.0 (6) | C22B—O4B—H4B | 109.5 |
C6B—C1B—C7B | 121.8 (5) | C24B—O5B—H5B1 | 109.5 |
C3B—C2B—C1B | 122.4 (6) | H61—O6—H62 | 89.8 |
C3B—C2B—H2B | 118.8 | C10A—S1A—C7A | 93.0 (2) |
C1B—C2B—H2B | 118.8 | C10B—S1B—C7B | 92.6 (3) |
C4B—C3B—C2B | 117.5 (6) | ||
C6A—C1A—C2A—C3A | −0.9 (8) | C7B—C1B—C6B—C5B | −176.1 (5) |
C7A—C1A—C2A—C3A | 176.6 (5) | C4B—C5B—C6B—C1B | 1.6 (10) |
C1A—C2A—C3A—C4A | 0.9 (8) | C2B—C1B—C7B—C8B | 20.5 (9) |
C2A—C3A—C4A—C5A | −1.0 (10) | C6B—C1B—C7B—C8B | −162.9 (6) |
C2A—C3A—C4A—F1A | −179.0 (5) | C2B—C1B—C7B—S1B | −156.6 (4) |
C3A—C4A—C5A—C6A | 1.1 (9) | C6B—C1B—C7B—S1B | 20.1 (7) |
F1A—C4A—C5A—C6A | 179.1 (5) | C1B—C7B—C8B—C9B | −177.8 (5) |
C4A—C5A—C6A—C1A | −1.0 (9) | S1B—C7B—C8B—C9B | −0.5 (6) |
C2A—C1A—C6A—C5A | 0.9 (8) | C7B—C8B—C9B—C10B | 0.6 (7) |
C7A—C1A—C6A—C5A | −176.5 (5) | C8B—C9B—C10B—C11B | −178.3 (5) |
C6A—C1A—C7A—C8A | −161.5 (6) | C8B—C9B—C10B—S1B | −0.3 (6) |
C2A—C1A—C7A—C8A | 21.2 (8) | C9B—C10B—C11B—C12B | 108.0 (6) |
C6A—C1A—C7A—S1A | 24.2 (6) | S1B—C10B—C11B—C12B | −69.8 (5) |
C2A—C1A—C7A—S1A | −153.1 (4) | C10B—C11B—C12B—C13B | −84.3 (5) |
C1A—C7A—C8A—C9A | −174.5 (5) | C10B—C11B—C12B—C17B | 93.7 (6) |
S1A—C7A—C8A—C9A | 0.2 (6) | C17B—C12B—C13B—C14B | −0.6 (7) |
C7A—C8A—C9A—C10A | 0.9 (7) | C11B—C12B—C13B—C14B | 177.4 (4) |
C8A—C9A—C10A—C11A | 178.1 (5) | C12B—C13B—C14B—C15B | −0.7 (6) |
C8A—C9A—C10A—S1A | −1.5 (6) | C12B—C13B—C14B—C19B | 177.0 (4) |
C9A—C10A—C11A—C12A | 113.3 (6) | C13B—C14B—C15B—C16B | 1.4 (6) |
S1A—C10A—C11A—C12A | −67.1 (5) | C19B—C14B—C15B—C16B | −176.2 (4) |
C10A—C11A—C12A—C13A | 106.6 (5) | C14B—C15B—C16B—C17B | −0.9 (7) |
C10A—C11A—C12A—C17A | −71.5 (6) | C15B—C16B—C17B—C12B | −0.4 (7) |
C17A—C12A—C13A—C14A | −0.6 (7) | C15B—C16B—C17B—C18B | 178.1 (4) |
C11A—C12A—C13A—C14A | −178.7 (4) | C13B—C12B—C17B—C16B | 1.1 (7) |
C12A—C13A—C14A—C15A | 0.9 (7) | C11B—C12B—C17B—C16B | −176.8 (4) |
C12A—C13A—C14A—C19A | 179.8 (4) | C13B—C12B—C17B—C18B | −177.3 (4) |
C13A—C14A—C15A—C16A | −0.5 (7) | C11B—C12B—C17B—C18B | 4.7 (7) |
C19A—C14A—C15A—C16A | −179.5 (4) | C15B—C14B—C19B—O1B | −141.6 (4) |
C14A—C15A—C16A—C17A | −0.2 (8) | C13B—C14B—C19B—O1B | 40.9 (5) |
C15A—C16A—C17A—C12A | 0.5 (8) | C15B—C14B—C19B—C20B | 98.1 (5) |
C15A—C16A—C17A—C18A | −178.0 (5) | C13B—C14B—C19B—C20B | −79.5 (5) |
C13A—C12A—C17A—C16A | −0.1 (7) | O1B—C19B—C20B—O2B | 167.9 (3) |
C11A—C12A—C17A—C16A | 178.0 (4) | C14B—C19B—C20B—O2B | −72.9 (4) |
C13A—C12A—C17A—C18A | 178.3 (4) | O1B—C19B—C20B—C21B | 46.9 (5) |
C11A—C12A—C17A—C18A | −3.6 (7) | C14B—C19B—C20B—C21B | 166.2 (4) |
C13A—C14A—C19A—O1A | −132.3 (4) | O2B—C20B—C21B—O3B | 73.6 (4) |
C15A—C14A—C19A—O1A | 46.7 (5) | C19B—C20B—C21B—O3B | −166.5 (3) |
C13A—C14A—C19A—C20A | 107.5 (5) | O2B—C20B—C21B—C22B | −164.1 (3) |
C15A—C14A—C19A—C20A | −73.6 (5) | C19B—C20B—C21B—C22B | −44.2 (5) |
O1A—C19A—C20A—O2A | 178.0 (3) | O3B—C21B—C22B—O4B | −69.7 (4) |
C14A—C19A—C20A—O2A | −62.9 (5) | C20B—C21B—C22B—O4B | 167.8 (3) |
O1A—C19A—C20A—C21A | 54.8 (5) | O3B—C21B—C22B—C23B | 173.0 (3) |
C14A—C19A—C20A—C21A | 173.9 (4) | C20B—C21B—C22B—C23B | 50.5 (5) |
O2A—C20A—C21A—O3A | 67.4 (5) | O4B—C22B—C23B—O1B | 179.2 (3) |
C19A—C20A—C21A—O3A | −171.4 (3) | C21B—C22B—C23B—O1B | −60.8 (4) |
O2A—C20A—C21A—C22A | −172.5 (4) | O4B—C22B—C23B—C24B | 62.0 (5) |
C19A—C20A—C21A—C22A | −51.4 (5) | C21B—C22B—C23B—C24B | −178.0 (4) |
O3A—C21A—C22A—O4A | −66.4 (4) | O1B—C23B—C24B—O5B | 67.8 (4) |
C20A—C21A—C22A—O4A | 171.0 (4) | C22B—C23B—C24B—O5B | −174.0 (4) |
O3A—C21A—C22A—C23A | 173.2 (3) | C22A—C23A—O1A—C19A | 61.0 (5) |
C20A—C21A—C22A—C23A | 50.5 (5) | C24A—C23A—O1A—C19A | 176.9 (4) |
O4A—C22A—C23A—O1A | −172.3 (3) | C14A—C19A—O1A—C23A | 175.6 (4) |
C21A—C22A—C23A—O1A | −53.9 (5) | C20A—C19A—O1A—C23A | −61.2 (5) |
O4A—C22A—C23A—C24A | 74.0 (4) | C14B—C19B—O1B—C23B | 178.8 (3) |
C21A—C22A—C23A—C24A | −167.6 (4) | C20B—C19B—O1B—C23B | −60.1 (4) |
O1A—C23A—C24A—O5A | 68.2 (5) | C24B—C23B—O1B—C19B | −169.8 (3) |
C22A—C23A—C24A—O5A | −174.7 (4) | C22B—C23B—O1B—C19B | 67.7 (4) |
C6B—C1B—C2B—C3B | −0.5 (9) | C9A—C10A—S1A—C7A | 1.4 (4) |
C7B—C1B—C2B—C3B | 176.3 (5) | C11A—C10A—S1A—C7A | −178.3 (4) |
C1B—C2B—C3B—C4B | −2.0 (10) | C8A—C7A—S1A—C10A | −0.9 (4) |
C2B—C3B—C4B—C5B | 4.7 (11) | C1A—C7A—S1A—C10A | 174.5 (4) |
C2B—C3B—C4B—F1B | −177.5 (6) | C9B—C10B—S1B—C7B | 0.0 (4) |
C3B—C4B—C5B—C6B | −4.5 (11) | C11B—C10B—S1B—C7B | 178.1 (4) |
F1B—C4B—C5B—C6B | 177.7 (6) | C8B—C7B—S1B—C10B | 0.3 (4) |
C2B—C1B—C6B—C5B | 0.7 (8) | C1B—C7B—S1B—C10B | 177.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H2A1···O2Bi | 0.82 | 2.42 | 2.841 (4) | 113 |
O3A—H3A1···O2Bi | 0.82 | 2.17 | 2.951 (4) | 158 |
O4A—H4A···O5Bii | 0.82 | 1.98 | 2.756 (5) | 157 |
O2B—H2B1···O4Aiii | 0.82 | 1.85 | 2.672 (4) | 179 |
O3B—H3B1···O4Bi | 0.82 | 1.99 | 2.797 (4) | 168 |
O4B—H4B···O6 | 0.82 | 1.93 | 2.749 (5) | 172 |
O5B—H5B1···O3Biv | 0.82 | 2.31 | 3.015 (5) | 144 |
O6—H61···O2A | 0.82 | 2.23 | 3.031 (5) | 166 |
O6—H62···O3Av | 0.83 | 2.30 | 3.058 (5) | 153 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) x−1, y−1, z; (iii) x, y+1, z; (iv) x+1, y, z; (v) x+1/2, −y+1/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H2A1···O2Bi | 0.82 | 2.42 | 2.841 (4) | 113 |
O3A—H3A1···O2Bi | 0.82 | 2.17 | 2.951 (4) | 158 |
O4A—H4A···O5Bii | 0.82 | 1.98 | 2.756 (5) | 157 |
O2B—H2B1···O4Aiii | 0.82 | 1.85 | 2.672 (4) | 179 |
O3B—H3B1···O4Bi | 0.82 | 1.99 | 2.797 (4) | 168 |
O4B—H4B···O6 | 0.82 | 1.93 | 2.749 (5) | 172 |
O5B—H5B1···O3Biv | 0.82 | 2.31 | 3.015 (5) | 144 |
O6—H61···O2A | 0.82 | 2.23 | 3.031 (5) | 166 |
O6—H62···O3Av | 0.83 | 2.30 | 3.058 (5) | 153 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) x−1, y−1, z; (iii) x, y+1, z; (iv) x+1, y, z; (v) x+1/2, −y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | 2C24H25FO5S·H2O |
Mr | 907.02 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 8.4259 (4), 11.4264 (7), 45.706 (2) |
V (Å3) | 4400.4 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.48 × 0.28 × 0.26 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.914, 0.952 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 43211, 9958, 5079 |
Rint | 0.145 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.080, 0.147, 1.00 |
No. of reflections | 9958 |
No. of parameters | 575 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.29 |
Absolute structure | Flack (1983), 3246 Friedel pairs |
Absolute structure parameter | 0.13 (11) |
Computer programs: PROCESS-AUTO (Rigaku, 2006), CrystalStructure (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 2012).
Acknowledgements
This project was supported by the Analysis and Measurement Foundation of Zhejiang Province, China (grant No. 2014 C37055).
References
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