organic compounds
9-(2-Chlorophenyl)-4a-hydroxy-3,4,4a,5,6,7,9,9a-octahydro-2H-xanthene-1,8-dione
aJiangsu University of Science and Technology, Zhenjiang 212003, People's Republic of China
*Correspondence e-mail: wangfmzj@just.edu.cn
In the title compound, C19H19ClO4, the dihydropyran ring and the cyclohexane ring adopt a half-chair conformation and a chair conformation, respectively. The cyclohexene ring has an with the central CH2 C atom as the flap. This atom is disordered over two positions [site-occupancy ratio = 0.744 (12):0.256 (12)] above and below the mean plane formed by the other five atoms. In the crystal, O—H⋯O hydrogen bonds between hydroxy and carbonyl groups link molecules into chains propagating along [001].
CCDC reference: 990638
Related literature
For the background, synthesis and activities of xanthenes, see: Knight & Stephens (1989); Srividya et al. (1996); Menchen et al. (2003); Reddy et al. (2009); Mehdi et al. (2011); Altieri et al.(2013). For related structures, see: Hua et al. (2006); Yang et al. (2011).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 990638
10.1107/S1600536814005297/xu5775sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814005297/xu5775Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814005297/xu5775Isup3.cml
Xanthenes and its derivatives are an important class of organic compounds with biological and pharmacological activity, such as antitumoral, fungicidal, anti-inflammatory, bactericidal properties, and so on. (Knight & Stephens, 1989; Srividya et al., 1996; Menchen et al., 2003; Reddy et al., 2009; Mehdi et al., 2011). In addition, xanthene derivatives are essential synthetic intermediates in
synthesis (Altieri et al., 2013).In the main structure of this compound (Figure 1), there exist central dihydropyran ring (O1/C5/C6/C7/C8/C13) adopts a half-chair conformations while the cyclohexane ring adopts a chair conformation. The cyclohexene ring displays an approximate
and in the crystal this ring is disordered over two positions in an occupancy ratio of 0.744 (12):0.256 (12) with the flap atom located on the opposite sides of the mean plane formed by other five atoms. The bond lengths and angles are comparable to those in a related structure (Hua et al., 2006; Yang et al., 2011). The crystal packing is stabilized by intermolecular O—H···O hydrogen bond between hydroxyl and carbonyl groups, which links the molecules into supramolecular chains running along the c-axis direction.1H NMR (400 MHz, DMSO-d6) δ: 7.11-7.31 (m, 4H), 6.93(s, 1H), 4.63(s, 1H), 3.06(s, 1H), 2.39(m, 3H), 2.21(m, 4H), 2.02(m, 2H), 1.85(m, 2H),1.58(m, 1H); IR (KBr pellet): 3442(br), 2962(m), 1711(m), 1640(m), 1609(s), 1389(s), 1079(s) ,773(m); MS (ESI) m/z : 347.1 (M—H+).
To a 100 mL flask, there were added 1,3-cyclohexanedione (4.5 g, 40mmol) and 2-chloro-benzaldehyde (2.8 g, 20mmol)in 40mL methanol, using L-proline (0.5 g) as the catalyst. The mixture were stirred at room temperature for 8h. The white precipitate was vacuum filtered and washed with methanol. And Then dried under vacuum to yield the white solid (6.1 g, 88% yield).
Single crystals of the title compound suitable for X-ray
were obtained by slow evaporation from mixture solution of anhydrous ethanol and dichloromethane (v: v = 1:1) at room temperature to yield colorless, block-shaped crystal.Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008; molecular graphics: SHELXTL (Sheldrick, 2008; software used to prepare material for publication: SHELXTL (Sheldrick, 2008.C19H19ClO4 | F(000) = 728 |
Mr = 346.79 | Dx = 1.406 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2557 reflections |
a = 15.3099 (13) Å | θ = 2.6–22.6° |
b = 9.2815 (8) Å | µ = 0.25 mm−1 |
c = 12.3216 (11) Å | T = 291 K |
β = 110.716 (1)° | Block, colorless |
V = 1637.7 (2) Å3 | 0.25 × 0.23 × 0.18 mm |
Z = 4 |
Bruker SMART APEXII CCD area-detector diffractometer | 3207 independent reflections |
Radiation source: sealed tube | 2208 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ϕ and ω scans | θmax = 26.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −18→18 |
Tmin = 0.94, Tmax = 0.96 | k = −11→11 |
12319 measured reflections | l = −15→15 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0852P)2] where P = (Fo2 + 2Fc2)/3 |
3207 reflections | (Δ/σ)max < 0.001 |
227 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C19H19ClO4 | V = 1637.7 (2) Å3 |
Mr = 346.79 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.3099 (13) Å | µ = 0.25 mm−1 |
b = 9.2815 (8) Å | T = 291 K |
c = 12.3216 (11) Å | 0.25 × 0.23 × 0.18 mm |
β = 110.716 (1)° |
Bruker SMART APEXII CCD area-detector diffractometer | 3207 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2208 reflections with I > 2σ(I) |
Tmin = 0.94, Tmax = 0.96 | Rint = 0.037 |
12319 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.24 e Å−3 |
3207 reflections | Δρmin = −0.24 e Å−3 |
227 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.36292 (16) | 0.6212 (3) | 0.22858 (19) | 0.0374 (5) | |
C2 | 0.4586 (2) | 0.5704 (3) | 0.3045 (3) | 0.0679 (9) | |
H2A | 0.4519 | 0.5038 | 0.3618 | 0.082* | |
H2B | 0.4865 | 0.5178 | 0.2569 | 0.082* | |
C3 | 0.5220 (3) | 0.6854 (6) | 0.3646 (6) | 0.0557 (18) | 0.744 (12) |
H3A | 0.5405 | 0.7363 | 0.3075 | 0.067* | 0.744 (12) |
H3B | 0.5778 | 0.6441 | 0.4211 | 0.067* | 0.744 (12) |
C3' | 0.4986 (10) | 0.6331 (16) | 0.4163 (11) | 0.048 (4) | 0.256 (12) |
H3'A | 0.5649 | 0.6240 | 0.4362 | 0.058* | 0.256 (12) |
H3'B | 0.4820 | 0.5808 | 0.4733 | 0.058* | 0.256 (12) |
C4 | 0.48086 (16) | 0.7929 (3) | 0.4227 (2) | 0.0474 (7) | |
H4A | 0.5185 | 0.8798 | 0.4380 | 0.057* | |
H4B | 0.4826 | 0.7543 | 0.4966 | 0.057* | |
C5 | 0.38240 (15) | 0.8304 (2) | 0.35106 (17) | 0.0325 (5) | |
C6 | 0.32588 (14) | 0.7506 (2) | 0.26163 (17) | 0.0304 (5) | |
C7 | 0.22743 (14) | 0.7965 (2) | 0.19183 (17) | 0.0294 (5) | |
H7A | 0.2224 | 0.7950 | 0.1103 | 0.035* | |
C8 | 0.21218 (14) | 0.9542 (2) | 0.21988 (16) | 0.0287 (5) | |
H8A | 0.1447 | 0.9677 | 0.1986 | 0.034* | |
C9 | 0.24489 (16) | 1.0626 (3) | 0.14999 (18) | 0.0368 (5) | |
C10 | 0.2394 (2) | 1.2177 (3) | 0.1799 (2) | 0.0475 (6) | |
H10A | 0.1745 | 1.2456 | 0.1591 | 0.057* | |
H10B | 0.2671 | 1.2769 | 0.1357 | 0.057* | |
C11 | 0.29051 (17) | 1.2435 (3) | 0.3093 (2) | 0.0408 (6) | |
H11A | 0.3568 | 1.2265 | 0.3284 | 0.049* | |
H11B | 0.2822 | 1.3429 | 0.3278 | 0.049* | |
C12 | 0.25337 (16) | 1.1442 (3) | 0.38055 (19) | 0.0374 (6) | |
H12A | 0.2898 | 1.1578 | 0.4621 | 0.045* | |
H12B | 0.1893 | 1.1705 | 0.3685 | 0.045* | |
C13 | 0.25672 (14) | 0.9869 (2) | 0.35002 (17) | 0.0296 (5) | |
C14 | 0.15332 (15) | 0.6935 (2) | 0.20126 (18) | 0.0308 (5) | |
C15 | 0.06507 (16) | 0.6870 (2) | 0.11488 (19) | 0.0364 (5) | |
C16 | −0.00219 (17) | 0.5888 (3) | 0.1178 (2) | 0.0461 (6) | |
H16A | −0.0601 | 0.5866 | 0.0582 | 0.055* | |
C17 | 0.01752 (18) | 0.4942 (3) | 0.2097 (2) | 0.0491 (7) | |
H17A | −0.0268 | 0.4268 | 0.2119 | 0.059* | |
C18 | 0.10288 (18) | 0.5000 (3) | 0.2982 (2) | 0.0450 (6) | |
H18A | 0.1157 | 0.4378 | 0.3611 | 0.054* | |
C19 | 0.17003 (16) | 0.5983 (2) | 0.29409 (19) | 0.0364 (5) | |
H19A | 0.2275 | 0.6007 | 0.3545 | 0.044* | |
Cl1 | 0.03711 (4) | 0.80536 (8) | −0.00262 (5) | 0.0547 (2) | |
O1 | 0.35645 (10) | 0.95441 (16) | 0.38789 (12) | 0.0361 (4) | |
O2 | 0.31864 (12) | 0.55190 (18) | 0.14146 (13) | 0.0472 (5) | |
O3 | 0.27329 (14) | 1.0251 (2) | 0.07442 (15) | 0.0588 (5) | |
O4 | 0.21588 (11) | 0.89704 (16) | 0.40837 (12) | 0.0387 (4) | |
H4O | 0.2496 | 0.8920 | 0.4769 | 0.058* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0396 (13) | 0.0346 (13) | 0.0383 (12) | 0.0004 (10) | 0.0139 (10) | −0.0021 (10) |
C2 | 0.0515 (18) | 0.0584 (19) | 0.078 (2) | 0.0237 (15) | 0.0032 (15) | −0.0164 (16) |
C3 | 0.028 (2) | 0.049 (3) | 0.082 (4) | 0.0068 (18) | 0.009 (2) | −0.012 (3) |
C3' | 0.036 (7) | 0.058 (8) | 0.040 (6) | 0.010 (6) | 0.001 (5) | 0.010 (5) |
C4 | 0.0312 (13) | 0.0437 (16) | 0.0537 (14) | 0.0042 (11) | −0.0020 (11) | −0.0068 (12) |
C5 | 0.0302 (12) | 0.0337 (13) | 0.0322 (11) | 0.0010 (10) | 0.0093 (9) | −0.0022 (9) |
C6 | 0.0281 (11) | 0.0311 (12) | 0.0308 (10) | −0.0014 (9) | 0.0089 (9) | −0.0009 (9) |
C7 | 0.0275 (11) | 0.0328 (12) | 0.0254 (10) | −0.0014 (9) | 0.0064 (8) | −0.0030 (8) |
C8 | 0.0258 (11) | 0.0289 (11) | 0.0292 (10) | −0.0023 (9) | 0.0070 (8) | −0.0001 (9) |
C9 | 0.0373 (13) | 0.0400 (14) | 0.0280 (11) | −0.0077 (10) | 0.0052 (9) | 0.0007 (9) |
C10 | 0.0578 (16) | 0.0362 (14) | 0.0457 (14) | −0.0037 (12) | 0.0149 (12) | 0.0069 (11) |
C11 | 0.0434 (14) | 0.0301 (13) | 0.0463 (13) | −0.0036 (11) | 0.0129 (11) | −0.0038 (10) |
C12 | 0.0381 (13) | 0.0355 (13) | 0.0388 (12) | 0.0011 (10) | 0.0138 (10) | −0.0054 (10) |
C13 | 0.0281 (11) | 0.0308 (12) | 0.0298 (10) | −0.0006 (9) | 0.0101 (9) | −0.0010 (9) |
C14 | 0.0290 (11) | 0.0291 (12) | 0.0334 (10) | −0.0005 (9) | 0.0098 (9) | −0.0080 (9) |
C15 | 0.0334 (12) | 0.0380 (14) | 0.0353 (11) | −0.0004 (10) | 0.0092 (9) | −0.0054 (10) |
C16 | 0.0298 (13) | 0.0542 (17) | 0.0524 (14) | −0.0094 (12) | 0.0123 (11) | −0.0158 (13) |
C17 | 0.0439 (15) | 0.0463 (16) | 0.0654 (17) | −0.0161 (12) | 0.0298 (13) | −0.0139 (13) |
C18 | 0.0543 (16) | 0.0380 (15) | 0.0505 (14) | −0.0036 (12) | 0.0281 (12) | −0.0005 (11) |
C19 | 0.0358 (12) | 0.0347 (13) | 0.0381 (12) | −0.0038 (10) | 0.0122 (10) | −0.0025 (10) |
Cl1 | 0.0444 (4) | 0.0587 (5) | 0.0442 (4) | −0.0027 (3) | −0.0052 (3) | 0.0053 (3) |
O1 | 0.0286 (8) | 0.0362 (9) | 0.0366 (8) | 0.0016 (7) | 0.0031 (6) | −0.0094 (7) |
O2 | 0.0585 (11) | 0.0397 (10) | 0.0387 (9) | 0.0032 (8) | 0.0114 (8) | −0.0113 (8) |
O3 | 0.0818 (14) | 0.0590 (12) | 0.0456 (10) | −0.0228 (11) | 0.0348 (10) | −0.0083 (9) |
O4 | 0.0442 (9) | 0.0397 (10) | 0.0322 (8) | −0.0043 (8) | 0.0136 (7) | 0.0019 (7) |
C1—O2 | 1.229 (3) | C8—H8A | 0.9800 |
C1—C6 | 1.447 (3) | C9—O3 | 1.210 (3) |
C1—C2 | 1.509 (3) | C9—C10 | 1.495 (3) |
C2—C3' | 1.419 (11) | C10—C11 | 1.526 (3) |
C2—C3 | 1.456 (5) | C10—H10A | 0.9700 |
C2—H2A | 0.9700 | C10—H10B | 0.9700 |
C2—H2B | 0.9700 | C11—C12 | 1.515 (3) |
C3—C4 | 1.490 (5) | C11—H11A | 0.9700 |
C3—H3A | 0.9700 | C11—H11B | 0.9700 |
C3—H3B | 0.9700 | C12—C13 | 1.513 (3) |
C3—H3'A | 1.0608 | C12—H12A | 0.9700 |
C3'—C4 | 1.514 (13) | C12—H12B | 0.9700 |
C3'—H3B | 1.1976 | C13—O4 | 1.386 (2) |
C3'—H3'A | 0.9601 | C13—O1 | 1.461 (2) |
C3'—H3'B | 0.9599 | C14—C15 | 1.395 (3) |
C4—C5 | 1.494 (3) | C14—C19 | 1.396 (3) |
C4—H4A | 0.9700 | C15—C16 | 1.385 (3) |
C4—H4B | 0.9700 | C15—Cl1 | 1.746 (2) |
C5—O1 | 1.348 (3) | C16—C17 | 1.380 (4) |
C5—C6 | 1.355 (3) | C16—H16A | 0.9300 |
C6—C7 | 1.509 (3) | C17—C18 | 1.375 (4) |
C7—C14 | 1.519 (3) | C17—H17A | 0.9300 |
C7—C8 | 1.541 (3) | C18—C19 | 1.389 (3) |
C7—H7A | 0.9800 | C18—H18A | 0.9300 |
C8—C9 | 1.520 (3) | C19—H19A | 0.9300 |
C8—C13 | 1.535 (3) | O4—H4O | 0.8200 |
O2—C1—C6 | 122.0 (2) | C8—C7—H7A | 106.3 |
O2—C1—C2 | 119.5 (2) | C9—C8—C13 | 110.33 (17) |
C6—C1—C2 | 118.4 (2) | C9—C8—C7 | 113.29 (17) |
C3'—C2—C3 | 39.2 (6) | C13—C8—C7 | 112.07 (17) |
C3'—C2—C1 | 117.7 (5) | C9—C8—H8A | 106.9 |
C3—C2—C1 | 114.3 (3) | C13—C8—H8A | 106.9 |
C3'—C2—H2A | 71.1 | C7—C8—H8A | 106.9 |
C3—C2—H2A | 108.7 | O3—C9—C10 | 122.2 (2) |
C1—C2—H2A | 108.7 | O3—C9—C8 | 121.7 (2) |
C3'—C2—H2B | 131.5 | C10—C9—C8 | 116.0 (2) |
C3—C2—H2B | 108.7 | C9—C10—C11 | 110.9 (2) |
C1—C2—H2B | 108.7 | C9—C10—H10A | 109.5 |
H2A—C2—H2B | 107.6 | C11—C10—H10A | 109.5 |
C2—C3—C4 | 114.6 (4) | C9—C10—H10B | 109.5 |
C2—C3—H3A | 107.5 | C11—C10—H10B | 109.5 |
C4—C3—H3A | 107.7 | H10A—C10—H10B | 108.1 |
C2—C3—H3B | 109.5 | C12—C11—C10 | 110.56 (19) |
C4—C3—H3B | 109.6 | C12—C11—H11A | 109.5 |
H3A—C3—H3B | 107.6 | C10—C11—H11A | 109.5 |
C2—C3—H3'A | 97.7 | C12—C11—H11B | 109.5 |
C4—C3—H3'A | 101.8 | C10—C11—H11B | 109.5 |
H3A—C3—H3'A | 127.7 | H11A—C11—H11B | 108.1 |
H3B—C3—H3'A | 20.2 | C13—C12—C11 | 112.95 (18) |
C2—C3'—C4 | 115.4 (8) | C13—C12—H12A | 109.0 |
C2—C3'—H3B | 99.5 | C11—C12—H12A | 109.0 |
C4—C3'—H3B | 96.4 | C13—C12—H12B | 109.0 |
C2—C3'—H3'A | 105.4 | C11—C12—H12B | 109.0 |
C4—C3'—H3'A | 105.5 | H12A—C12—H12B | 107.8 |
H3B—C3'—H3'A | 15.0 | O4—C13—O1 | 108.80 (16) |
C2—C3'—H3'B | 111.6 | O4—C13—C12 | 112.99 (17) |
C4—C3'—H3'B | 111.0 | O1—C13—C12 | 104.07 (16) |
H3B—C3'—H3'B | 122.2 | O4—C13—C8 | 107.92 (16) |
H3'A—C3'—H3'B | 107.3 | O1—C13—C8 | 108.71 (16) |
C3—C4—C5 | 112.5 (2) | C12—C13—C8 | 114.14 (18) |
C3—C4—C3' | 37.4 (5) | C15—C14—C19 | 116.4 (2) |
C5—C4—C3' | 111.1 (5) | C15—C14—C7 | 121.16 (19) |
C3—C4—H4A | 109.1 | C19—C14—C7 | 122.39 (19) |
C5—C4—H4A | 109.1 | C16—C15—C14 | 122.5 (2) |
C3'—C4—H4A | 136.0 | C16—C15—Cl1 | 117.97 (18) |
C3—C4—H4B | 109.1 | C14—C15—Cl1 | 119.50 (17) |
C5—C4—H4B | 109.1 | C17—C16—C15 | 119.4 (2) |
C3'—C4—H4B | 75.0 | C17—C16—H16A | 120.3 |
H4A—C4—H4B | 107.8 | C15—C16—H16A | 120.3 |
O1—C5—C6 | 124.11 (19) | C18—C17—C16 | 119.8 (2) |
O1—C5—C4 | 110.88 (18) | C18—C17—H17A | 120.1 |
C6—C5—C4 | 125.0 (2) | C16—C17—H17A | 120.1 |
C5—C6—C1 | 118.8 (2) | C17—C18—C19 | 120.3 (2) |
C5—C6—C7 | 122.1 (2) | C17—C18—H18A | 119.9 |
C1—C6—C7 | 119.07 (18) | C19—C18—H18A | 119.9 |
C6—C7—C14 | 113.68 (17) | C18—C19—C14 | 121.5 (2) |
C6—C7—C8 | 109.90 (16) | C18—C19—H19A | 119.2 |
C14—C7—C8 | 113.82 (17) | C14—C19—H19A | 119.2 |
C6—C7—H7A | 106.3 | C5—O1—C13 | 117.90 (16) |
C14—C7—H7A | 106.3 | C13—O4—H4O | 109.5 |
O2—C1—C2—C3' | −166.3 (10) | C7—C8—C9—C10 | −175.13 (18) |
C6—C1—C2—C3' | 13.3 (10) | O3—C9—C10—C11 | −126.3 (2) |
O2—C1—C2—C3 | 150.0 (4) | C8—C9—C10—C11 | 53.9 (3) |
C6—C1—C2—C3 | −30.3 (5) | C9—C10—C11—C12 | −55.0 (3) |
C3'—C2—C3—C4 | −57.7 (7) | C10—C11—C12—C13 | 54.7 (3) |
C1—C2—C3—C4 | 46.9 (7) | C11—C12—C13—O4 | −175.08 (17) |
C3—C2—C3'—C4 | 56.8 (10) | C11—C12—C13—O1 | 67.1 (2) |
C1—C2—C3'—C4 | −38.5 (17) | C11—C12—C13—C8 | −51.3 (2) |
C2—C3—C4—C5 | −40.4 (7) | C9—C8—C13—O4 | 172.60 (17) |
C2—C3—C4—C3' | 55.3 (7) | C7—C8—C13—O4 | −60.2 (2) |
C2—C3'—C4—C3 | −58.2 (10) | C9—C8—C13—O1 | −69.5 (2) |
C2—C3'—C4—C5 | 41.6 (15) | C7—C8—C13—O1 | 57.7 (2) |
C3—C4—C5—O1 | −162.2 (4) | C9—C8—C13—C12 | 46.1 (2) |
C3'—C4—C5—O1 | 157.5 (8) | C7—C8—C13—C12 | 173.36 (17) |
C3—C4—C5—C6 | 18.4 (5) | C6—C7—C14—C15 | −156.35 (19) |
C3'—C4—C5—C6 | −22.0 (9) | C8—C7—C14—C15 | 76.8 (2) |
O1—C5—C6—C1 | 178.4 (2) | C6—C7—C14—C19 | 21.9 (3) |
C4—C5—C6—C1 | −2.2 (3) | C8—C7—C14—C19 | −105.0 (2) |
O1—C5—C6—C7 | 1.6 (3) | C19—C14—C15—C16 | −2.0 (3) |
C4—C5—C6—C7 | −179.0 (2) | C7—C14—C15—C16 | 176.3 (2) |
O2—C1—C6—C5 | −172.6 (2) | C19—C14—C15—Cl1 | 178.38 (16) |
C2—C1—C6—C5 | 7.7 (3) | C7—C14—C15—Cl1 | −3.3 (3) |
O2—C1—C6—C7 | 4.3 (3) | C14—C15—C16—C17 | 0.7 (3) |
C2—C1—C6—C7 | −175.3 (2) | Cl1—C15—C16—C17 | −179.66 (19) |
C5—C6—C7—C14 | −116.6 (2) | C15—C16—C17—C18 | 1.1 (4) |
C1—C6—C7—C14 | 66.6 (2) | C16—C17—C18—C19 | −1.5 (4) |
C5—C6—C7—C8 | 12.3 (3) | C17—C18—C19—C14 | 0.1 (3) |
C1—C6—C7—C8 | −164.54 (18) | C15—C14—C19—C18 | 1.6 (3) |
C6—C7—C8—C9 | 84.2 (2) | C7—C14—C19—C18 | −176.7 (2) |
C14—C7—C8—C9 | −147.02 (17) | C6—C5—O1—C13 | 15.9 (3) |
C6—C7—C8—C13 | −41.5 (2) | C4—C5—O1—C13 | −163.57 (18) |
C14—C7—C8—C13 | 87.3 (2) | O4—C13—O1—C5 | 72.7 (2) |
C13—C8—C9—O3 | 131.7 (2) | C12—C13—O1—C5 | −166.63 (17) |
C7—C8—C9—O3 | 5.1 (3) | C8—C13—O1—C5 | −44.6 (2) |
C13—C8—C9—C10 | −48.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O2i | 0.82 | 2.00 | 2.784 (2) | 161 |
Symmetry code: (i) x, −y+3/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O2i | 0.82 | 2.00 | 2.784 (2) | 161 |
Symmetry code: (i) x, −y+3/2, z+1/2. |
Acknowledgements
This work is supported by projects from the National Natural Science Foundation of China for Young Scholars (grant No. 21201087), the Natural Science Foundation of Jiangsu Provincial Department of Education (grant No. 11KJB150004), the Natural Science Foundation of Jiangsu Province of China (grant No. BK20131244, BK20130460) and The Starting-up Foundation of Jiangsu University of Science and Technology.
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