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The title compound, C38H50O6, also known as guttiferone A, was isolated from the medicinal plant Symphonia globulifera. It is a benzophenone derivative where one aryl group is derivatized to give a bicyclic system which has two prenyl groups attached to the bridgehead. One of the cyclo­hexane rings in the bicyclic system is in a chair form, while the other has a distorted half-chair conformation. In addition to an intra­molecular O—H...O hydrogen bond, inter­molecular O—H...O hydrogen bonds link mol­ecules into one-dimensional chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807005776/lh2291sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807005776/lh2291Isup2.hkl
Contains datablock I

CCDC reference: 640409

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.047
  • wR factor = 0.105
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.14 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.67 Ratio
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C36
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 29.13 From the CIF: _reflns_number_total 5171 Count of symmetry unique reflns 5207 Completeness (_total/calc) 99.31% 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 no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C25 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C26 = . S
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: .. Identification and collection of plant, fractionation of extract and isolation were made at the Departement of Organic Chemistry, Faculty of Science, University of Yaounde 1, Cameroon by Bruno Ndjakou Lenta, Silvere Ngouela and Etienne Tsamo. Crystallisation, NMR , Xray analysis , interpretation of data were carried on at Bielefed University by Bruno Ndjakou Lenta, Norbert Sewald, Krishna Prasad Devkota and Patrice Aime Fokou .

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON98 (Spek, 1998); software used to prepare material for publication: SHELXL97.

(1R,5R,7R,8S)-3-(3,4-Dihydroxybenzoyl)-4-hydroxy-8-methyl-1,5,7-tris(3- methyl-2-butenyl)-8-(4-methyl-3-pentenyl)bicyclo[3.3.1]non-3-ene-2,9-dione top
Crystal data top
C38H50O6F(000) = 1304
Mr = 602.78Dx = 1.160 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ac 2abCell parameters from 4991 reflections
a = 8.786 (1) Åθ = 1.0–29.1°
b = 11.449 (1) ŵ = 0.08 mm1
c = 34.306 (2) ÅT = 173 K
V = 3450.9 (5) Å3Prism, colorless
Z = 40.16 × 0.14 × 0.12 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
3899 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Graphite monochromatorθmax = 29.1°, θmin = 1.9°
φ scansh = 1212
9050 measured reflectionsk = 1515
5171 independent reflectionsl = 4646
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0482P)2 + 0.2481P]
where P = (Fo2 + 2Fc2)/3
5171 reflections(Δ/σ)max = 0.001
400 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.18 e Å3
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
xyzUiso*/Ueq
O1A0.67799 (18)0.21629 (16)0.07016 (4)0.0375 (4)
H1O0.74580.26520.07570.056*
O20.5018 (2)0.03885 (17)0.04626 (4)0.0466 (5)
H2O0.51710.06560.06870.070*
O3A0.86545 (17)0.06552 (16)0.09727 (4)0.0375 (4)
H3O0.86650.04250.12050.056*
O40.40429 (17)0.11708 (13)0.07929 (4)0.0299 (3)
O50.34069 (17)0.21458 (13)0.15260 (4)0.0325 (4)
O60.78963 (16)0.01873 (14)0.15805 (4)0.0299 (3)
C10.8115 (3)0.1848 (2)0.03061 (6)0.0334 (5)
H10.88560.21580.04790.040*
C20.8022 (3)0.2267 (2)0.00734 (6)0.0355 (5)
H20.86780.28760.01580.043*
C30.6972 (3)0.17935 (19)0.03258 (6)0.0290 (5)
C40.6032 (3)0.0881 (2)0.02065 (6)0.0304 (5)
C50.6089 (3)0.04798 (19)0.01720 (6)0.0293 (5)
H50.54280.01280.02550.035*
C60.7129 (2)0.09752 (19)0.04335 (6)0.0268 (4)
C70.7288 (2)0.05943 (19)0.08380 (6)0.0271 (5)
C80.6099 (2)0.01620 (17)0.10850 (5)0.0226 (4)
C90.4490 (2)0.04212 (18)0.10227 (5)0.0236 (4)
C100.3308 (2)0.01980 (18)0.12740 (5)0.0236 (4)
C110.3997 (2)0.11934 (18)0.15022 (5)0.0241 (4)
C120.5401 (2)0.08585 (18)0.17339 (5)0.0237 (4)
C130.6530 (2)0.02649 (18)0.14614 (5)0.0242 (4)
C140.1972 (2)0.0602 (2)0.10136 (6)0.0307 (5)
H14A0.14840.00930.08960.037*
H14B0.12040.09960.11790.037*
C150.2445 (3)0.1424 (2)0.06917 (7)0.0386 (6)
H150.29750.21080.07700.046*
C160.2207 (3)0.1299 (2)0.03130 (7)0.0438 (6)
C170.2746 (4)0.2221 (3)0.00251 (9)0.0731 (10)
H17A0.32290.28640.01670.110*
H17B0.18730.25190.01220.110*
H17C0.34830.18730.01550.110*
C180.1421 (4)0.0284 (3)0.01271 (8)0.0608 (8)
H18A0.12310.03200.03240.091*
H18B0.20670.00370.00800.091*
H18C0.04520.05430.00160.091*
C190.6197 (3)0.19799 (19)0.18872 (6)0.0284 (5)
H19A0.54520.24530.20360.034*
H19B0.70260.17560.20680.034*
C200.6844 (3)0.27072 (19)0.15624 (6)0.0304 (5)
H200.61400.29530.13690.036*
C210.8268 (3)0.30484 (19)0.15114 (7)0.0337 (5)
C220.9540 (3)0.2781 (3)0.17891 (8)0.0461 (7)
H22A0.95720.33790.19930.069*
H22B1.05090.27770.16480.069*
H22C0.93700.20140.19080.069*
C230.8743 (3)0.3757 (2)0.11631 (7)0.0512 (7)
H23A0.79030.37870.09750.077*
H23B0.96330.33950.10410.077*
H23C0.90010.45520.12460.077*
C240.2731 (2)0.06685 (18)0.15917 (6)0.0252 (4)
H24A0.18850.02930.17350.030*
H24B0.23140.13680.14600.030*
C250.3940 (3)0.10702 (18)0.18896 (5)0.0258 (4)
H250.33400.14020.21110.031*
C260.4825 (2)0.00143 (18)0.20710 (5)0.0249 (4)
C270.4929 (2)0.20993 (18)0.17429 (6)0.0275 (5)
H27A0.54970.18480.15080.033*
H27B0.56810.23050.19460.033*
C280.4004 (3)0.3162 (2)0.16449 (7)0.0357 (5)
H280.31820.33290.18160.043*
C290.4191 (3)0.3898 (2)0.13499 (7)0.0415 (6)
C300.5374 (3)0.3773 (2)0.10369 (8)0.0522 (7)
H30A0.58460.30000.10550.078*
H30B0.48940.38620.07810.078*
H30C0.61540.43770.10700.078*
C310.3210 (4)0.4970 (2)0.13093 (10)0.0644 (9)
H31A0.24510.49820.15190.097*
H31B0.38480.56700.13270.097*
H31C0.26920.49550.10560.097*
C320.6170 (3)0.0437 (2)0.23204 (6)0.0318 (5)
H32A0.66140.02270.24600.048*
H32B0.69440.07900.21510.048*
H32C0.58110.10190.25090.048*
C330.3751 (3)0.06942 (19)0.23428 (5)0.0297 (5)
H33A0.43680.12810.24840.036*
H33B0.30140.11240.21780.036*
C340.2854 (3)0.0028 (2)0.26450 (6)0.0343 (5)
H34A0.19700.04020.25160.041*
H34B0.35150.06540.27500.041*
C350.2300 (3)0.0736 (2)0.29769 (6)0.0317 (5)
H350.29980.08620.31840.038*
C360.0972 (3)0.1241 (2)0.30112 (6)0.0397 (6)
C370.0612 (3)0.2007 (3)0.33590 (8)0.0531 (7)
H37A0.14880.20210.35360.080*
H37B0.02760.16940.34960.080*
H37C0.03920.28020.32700.080*
C380.0300 (4)0.1075 (4)0.27284 (9)0.0936 (15)
H38A0.00970.07320.24870.140*
H38B0.07680.18320.26710.140*
H38C0.10640.05520.28420.140*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0370 (9)0.0493 (11)0.0263 (8)0.0056 (9)0.0026 (7)0.0089 (7)
O20.0570 (11)0.0550 (11)0.0279 (8)0.0199 (10)0.0025 (8)0.0025 (8)
O3A0.0245 (8)0.0554 (11)0.0327 (8)0.0025 (8)0.0001 (6)0.0161 (8)
O40.0273 (8)0.0326 (8)0.0298 (7)0.0031 (7)0.0018 (6)0.0094 (7)
O50.0326 (8)0.0234 (8)0.0417 (8)0.0032 (7)0.0049 (7)0.0040 (6)
O60.0221 (7)0.0372 (9)0.0303 (7)0.0015 (7)0.0029 (6)0.0067 (6)
C10.0299 (12)0.0387 (13)0.0315 (11)0.0088 (11)0.0022 (10)0.0055 (10)
C20.0343 (13)0.0395 (13)0.0325 (12)0.0104 (11)0.0026 (10)0.0092 (10)
C30.0306 (12)0.0337 (12)0.0227 (10)0.0011 (10)0.0054 (9)0.0036 (8)
C40.0314 (12)0.0331 (12)0.0266 (10)0.0015 (11)0.0034 (9)0.0035 (9)
C50.0287 (11)0.0288 (11)0.0304 (11)0.0045 (10)0.0074 (9)0.0004 (9)
C60.0257 (11)0.0299 (11)0.0248 (10)0.0006 (10)0.0043 (8)0.0032 (8)
C70.0235 (10)0.0261 (11)0.0317 (11)0.0021 (9)0.0026 (9)0.0033 (9)
C80.0230 (10)0.0216 (10)0.0232 (9)0.0010 (9)0.0022 (8)0.0020 (8)
C90.0252 (10)0.0244 (11)0.0214 (10)0.0017 (9)0.0010 (8)0.0003 (8)
C100.0209 (10)0.0226 (10)0.0274 (10)0.0001 (9)0.0015 (8)0.0021 (8)
C110.0245 (10)0.0223 (10)0.0253 (10)0.0036 (9)0.0078 (8)0.0014 (8)
C120.0250 (10)0.0226 (10)0.0237 (10)0.0036 (9)0.0035 (8)0.0038 (8)
C130.0232 (10)0.0221 (10)0.0272 (10)0.0024 (9)0.0016 (8)0.0011 (8)
C140.0243 (11)0.0324 (12)0.0353 (11)0.0017 (10)0.0007 (9)0.0048 (9)
C150.0361 (14)0.0338 (13)0.0459 (14)0.0008 (11)0.0068 (11)0.0054 (10)
C160.0419 (14)0.0453 (15)0.0443 (15)0.0114 (13)0.0047 (12)0.0089 (11)
C170.087 (3)0.075 (2)0.0572 (18)0.004 (2)0.0079 (18)0.0304 (17)
C180.073 (2)0.065 (2)0.0444 (15)0.0071 (19)0.0131 (14)0.0030 (14)
C190.0330 (12)0.0256 (11)0.0268 (10)0.0078 (10)0.0042 (9)0.0057 (8)
C200.0392 (13)0.0240 (10)0.0281 (11)0.0052 (10)0.0039 (10)0.0043 (9)
C210.0370 (13)0.0261 (11)0.0379 (12)0.0053 (10)0.0102 (10)0.0056 (9)
C220.0340 (14)0.0518 (16)0.0526 (15)0.0091 (13)0.0063 (12)0.0060 (13)
C230.0592 (18)0.0435 (15)0.0509 (15)0.0131 (15)0.0226 (14)0.0023 (12)
C240.0227 (10)0.0231 (10)0.0298 (10)0.0022 (9)0.0042 (8)0.0029 (8)
C250.0275 (11)0.0240 (10)0.0260 (10)0.0042 (10)0.0042 (9)0.0011 (8)
C260.0267 (11)0.0248 (11)0.0232 (10)0.0027 (9)0.0041 (8)0.0010 (8)
C270.0274 (11)0.0209 (10)0.0342 (11)0.0007 (9)0.0004 (9)0.0024 (8)
C280.0347 (13)0.0229 (11)0.0494 (14)0.0013 (11)0.0004 (11)0.0024 (10)
C290.0426 (14)0.0241 (12)0.0577 (15)0.0052 (11)0.0183 (12)0.0060 (11)
C300.0623 (18)0.0447 (16)0.0498 (15)0.0187 (15)0.0088 (14)0.0174 (12)
C310.070 (2)0.0266 (14)0.097 (2)0.0005 (15)0.0272 (18)0.0134 (13)
C320.0347 (12)0.0319 (12)0.0288 (11)0.0053 (11)0.0017 (9)0.0001 (9)
C330.0375 (12)0.0268 (11)0.0248 (10)0.0047 (10)0.0086 (9)0.0036 (8)
C340.0401 (13)0.0310 (12)0.0317 (11)0.0032 (11)0.0122 (10)0.0006 (9)
C350.0317 (12)0.0353 (13)0.0280 (11)0.0031 (11)0.0060 (9)0.0007 (9)
C360.0395 (14)0.0472 (15)0.0324 (12)0.0053 (13)0.0055 (10)0.0033 (11)
C370.0536 (17)0.0486 (17)0.0572 (16)0.0095 (15)0.0181 (14)0.0078 (13)
C380.070 (2)0.158 (4)0.0526 (18)0.051 (3)0.0222 (17)0.018 (2)
Geometric parameters (Å, º) top
O1A—C31.367 (2)C21—C221.500 (4)
O1A—H1O0.8400C21—C231.504 (3)
O2—C41.373 (3)C22—H22A0.9800
O2—H2O0.8400C22—H22B0.9800
O3A—C71.289 (3)C22—H22C0.9800
O3A—H3O0.8400C23—H23A0.9800
O4—C91.230 (2)C23—H23B0.9800
O5—C111.210 (3)C23—H23C0.9800
O6—C131.271 (2)C24—C251.544 (3)
C1—C21.390 (3)C24—H24A0.9900
C1—C61.393 (3)C24—H24B0.9900
C1—H10.9500C25—C271.548 (3)
C2—C31.377 (3)C25—C261.566 (3)
C2—H20.9500C25—H251.0000
C3—C41.393 (3)C26—C321.538 (3)
C4—C51.378 (3)C26—C331.555 (3)
C5—C61.400 (3)C27—C281.501 (3)
C5—H50.9500C27—H27A0.9900
C6—C71.461 (3)C27—H27B0.9900
C7—C81.433 (3)C28—C291.327 (3)
C8—C131.432 (3)C28—H280.9500
C8—C91.460 (3)C29—C301.501 (4)
C9—C101.524 (3)C29—C311.506 (4)
C10—C111.510 (3)C30—H30A0.9800
C10—C141.546 (3)C30—H30B0.9800
C10—C241.558 (3)C30—H30C0.9800
C11—C121.517 (3)C31—H31A0.9800
C12—C131.523 (3)C31—H31B0.9800
C12—C191.554 (3)C31—H31C0.9800
C12—C261.610 (3)C32—H32A0.9800
C14—C151.509 (3)C32—H32B0.9800
C14—H14A0.9900C32—H32C0.9800
C14—H14B0.9900C33—C341.543 (3)
C15—C161.324 (3)C33—H33A0.9900
C15—H150.9500C33—H33B0.9900
C16—C181.494 (4)C34—C351.516 (3)
C16—C171.521 (4)C34—H34A0.9900
C17—H17A0.9800C34—H34B0.9900
C17—H17B0.9800C35—C361.307 (4)
C17—H17C0.9800C35—H350.9500
C18—H18A0.9800C36—C381.492 (4)
C18—H18B0.9800C36—C371.514 (4)
C18—H18C0.9800C37—H37A0.9800
C19—C201.503 (3)C37—H37B0.9800
C19—H19A0.9900C37—H37C0.9800
C19—H19B0.9900C38—H38A0.9800
C20—C211.322 (3)C38—H38B0.9800
C20—H200.9500C38—H38C0.9800
C3—O1A—H1O109.5C21—C22—H22C109.5
C4—O2—H2O109.5H22A—C22—H22C109.5
C7—O3A—H3O109.5H22B—C22—H22C109.5
C2—C1—C6120.3 (2)C21—C23—H23A109.5
C2—C1—H1119.8C21—C23—H23B109.5
C6—C1—H1119.8H23A—C23—H23B109.5
C3—C2—C1119.5 (2)C21—C23—H23C109.5
C3—C2—H2120.2H23A—C23—H23C109.5
C1—C2—H2120.2H23B—C23—H23C109.5
O1A—C3—C2123.7 (2)C25—C24—C10115.40 (17)
O1A—C3—C4115.8 (2)C25—C24—H24A108.4
C2—C3—C4120.5 (2)C10—C24—H24A108.4
O2—C4—C5119.3 (2)C25—C24—H24B108.4
O2—C4—C3120.34 (19)C10—C24—H24B108.4
C5—C4—C3120.3 (2)H24A—C24—H24B107.5
C4—C5—C6119.5 (2)C24—C25—C27113.43 (17)
C4—C5—H5120.3C24—C25—C26112.00 (17)
C6—C5—H5120.3C27—C25—C26115.97 (18)
C1—C6—C5119.70 (18)C24—C25—H25104.7
C1—C6—C7116.9 (2)C27—C25—H25104.7
C5—C6—C7123.4 (2)C26—C25—H25104.7
O3A—C7—C8119.07 (18)C32—C26—C33107.30 (16)
O3A—C7—C6114.42 (19)C32—C26—C25111.07 (17)
C8—C7—C6126.50 (19)C33—C26—C25109.86 (17)
C13—C8—C7117.27 (18)C32—C26—C12110.70 (17)
C13—C8—C9117.24 (18)C33—C26—C12107.32 (16)
C7—C8—C9123.29 (18)C25—C26—C12110.47 (15)
O4—C9—C8123.01 (18)C28—C27—C25112.70 (18)
O4—C9—C10118.00 (18)C28—C27—H27A109.1
C8—C9—C10118.83 (17)C25—C27—H27A109.1
C11—C10—C9111.78 (17)C28—C27—H27B109.1
C11—C10—C14112.22 (18)C25—C27—H27B109.1
C9—C10—C14109.25 (15)H27A—C27—H27B107.8
C11—C10—C24104.38 (15)C29—C28—C27128.2 (2)
C9—C10—C24108.72 (16)C29—C28—H28115.9
C14—C10—C24110.35 (17)C27—C28—H28115.9
O5—C11—C10122.92 (19)C28—C29—C30124.8 (2)
O5—C11—C12122.74 (19)C28—C29—C31121.1 (3)
C10—C11—C12114.03 (18)C30—C29—C31114.1 (2)
C11—C12—C13108.73 (15)C29—C30—H30A109.5
C11—C12—C19109.54 (18)C29—C30—H30B109.5
C13—C12—C19106.48 (17)H30A—C30—H30B109.5
C11—C12—C26106.10 (16)C29—C30—H30C109.5
C13—C12—C26111.64 (17)H30A—C30—H30C109.5
C19—C12—C26114.27 (16)H30B—C30—H30C109.5
O6—C13—C8121.07 (19)C29—C31—H31A109.5
O6—C13—C12116.68 (17)C29—C31—H31B109.5
C8—C13—C12122.23 (18)H31A—C31—H31B109.5
C15—C14—C10113.59 (18)C29—C31—H31C109.5
C15—C14—H14A108.8H31A—C31—H31C109.5
C10—C14—H14A108.8H31B—C31—H31C109.5
C15—C14—H14B108.8C26—C32—H32A109.5
C10—C14—H14B108.8C26—C32—H32B109.5
H14A—C14—H14B107.7H32A—C32—H32B109.5
C16—C15—C14127.4 (2)C26—C32—H32C109.5
C16—C15—H15116.3H32A—C32—H32C109.5
C14—C15—H15116.3H32B—C32—H32C109.5
C15—C16—C18125.2 (3)C34—C33—C26115.68 (18)
C15—C16—C17120.9 (3)C34—C33—H33A108.4
C18—C16—C17114.0 (2)C26—C33—H33A108.4
C16—C17—H17A109.5C34—C33—H33B108.4
C16—C17—H17B109.5C26—C33—H33B108.4
H17A—C17—H17B109.5H33A—C33—H33B107.4
C16—C17—H17C109.5C35—C34—C33111.06 (19)
H17A—C17—H17C109.5C35—C34—H34A109.4
H17B—C17—H17C109.5C33—C34—H34A109.4
C16—C18—H18A109.5C35—C34—H34B109.4
C16—C18—H18B109.5C33—C34—H34B109.4
H18A—C18—H18B109.5H34A—C34—H34B108.0
C16—C18—H18C109.5C36—C35—C34127.6 (2)
H18A—C18—H18C109.5C36—C35—H35116.2
H18B—C18—H18C109.5C34—C35—H35116.2
C20—C19—C12112.16 (16)C35—C36—C38123.6 (2)
C20—C19—H19A109.2C35—C36—C37120.9 (2)
C12—C19—H19A109.2C38—C36—C37115.5 (2)
C20—C19—H19B109.2C36—C37—H37A109.5
C12—C19—H19B109.2C36—C37—H37B109.5
H19A—C19—H19B107.9H37A—C37—H37B109.5
C21—C20—C19128.3 (2)C36—C37—H37C109.5
C21—C20—H20115.8H37A—C37—H37C109.5
C19—C20—H20115.8H37B—C37—H37C109.5
C20—C21—C22124.1 (2)C36—C38—H38A109.5
C20—C21—C23121.8 (2)C36—C38—H38B109.5
C22—C21—C23114.1 (2)H38A—C38—H38B109.5
C21—C22—H22A109.5C36—C38—H38C109.5
C21—C22—H22B109.5H38A—C38—H38C109.5
H22A—C22—H22B109.5H38B—C38—H38C109.5
C6—C1—C2—C31.6 (4)C26—C12—C13—O680.1 (2)
C1—C2—C3—O1A178.8 (2)C11—C12—C13—C815.3 (3)
C1—C2—C3—C41.6 (4)C19—C12—C13—C8133.2 (2)
O1A—C3—C4—O21.6 (3)C26—C12—C13—C8101.4 (2)
C2—C3—C4—O2178.1 (2)C11—C10—C14—C1565.4 (2)
O1A—C3—C4—C5177.1 (2)C9—C10—C14—C1559.1 (2)
C2—C3—C4—C53.2 (3)C24—C10—C14—C15178.62 (18)
O2—C4—C5—C6179.6 (2)C10—C14—C15—C16124.4 (3)
C3—C4—C5—C61.7 (3)C14—C15—C16—C180.9 (5)
C2—C1—C6—C53.1 (3)C14—C15—C16—C17179.3 (3)
C2—C1—C6—C7179.2 (2)C11—C12—C19—C2066.6 (2)
C4—C5—C6—C11.5 (3)C13—C12—C19—C2050.8 (2)
C4—C5—C6—C7179.0 (2)C26—C12—C19—C20174.53 (18)
C1—C6—C7—O3A31.4 (3)C12—C19—C20—C21122.6 (2)
C5—C6—C7—O3A146.2 (2)C19—C20—C21—C221.8 (4)
C1—C6—C7—C8149.5 (2)C19—C20—C21—C23178.6 (2)
C5—C6—C7—C832.9 (3)C11—C10—C24—C2555.1 (2)
O3A—C7—C8—C134.7 (3)C9—C10—C24—C2564.3 (2)
C6—C7—C8—C13174.4 (2)C14—C10—C24—C25175.85 (17)
O3A—C7—C8—C9157.9 (2)C10—C24—C25—C2783.4 (2)
C6—C7—C8—C923.0 (3)C10—C24—C25—C2650.3 (2)
C13—C8—C9—O4150.92 (19)C24—C25—C26—C32171.79 (15)
C7—C8—C9—O411.7 (3)C27—C25—C26—C3239.4 (2)
C13—C8—C9—C1024.5 (3)C24—C25—C26—C3369.7 (2)
C7—C8—C9—C10172.91 (19)C27—C25—C26—C33157.99 (17)
O4—C9—C10—C11172.73 (17)C24—C25—C26—C1248.6 (2)
C8—C9—C10—C1111.7 (3)C27—C25—C26—C1283.8 (2)
O4—C9—C10—C1447.9 (2)C11—C12—C26—C32178.64 (16)
C8—C9—C10—C14136.48 (19)C13—C12—C26—C3260.3 (2)
O4—C9—C10—C2472.6 (2)C19—C12—C26—C3260.6 (2)
C8—C9—C10—C24103.0 (2)C11—C12—C26—C3364.6 (2)
C9—C10—C11—O5134.6 (2)C13—C12—C26—C33177.14 (17)
C14—C10—C11—O511.4 (3)C19—C12—C26—C3356.2 (2)
C24—C10—C11—O5108.1 (2)C11—C12—C26—C2555.2 (2)
C9—C10—C11—C1251.6 (2)C13—C12—C26—C2563.1 (2)
C14—C10—C11—C12174.77 (16)C19—C12—C26—C25175.99 (17)
C24—C10—C11—C1265.7 (2)C24—C25—C27—C2859.3 (2)
O5—C11—C12—C13133.6 (2)C26—C25—C27—C28169.03 (17)
C10—C11—C12—C1352.6 (2)C25—C27—C28—C29140.8 (2)
O5—C11—C12—C1917.6 (3)C27—C28—C29—C302.6 (4)
C10—C11—C12—C19168.63 (15)C27—C28—C29—C31176.2 (2)
O5—C11—C12—C26106.2 (2)C32—C26—C33—C3471.1 (2)
C10—C11—C12—C2667.6 (2)C25—C26—C33—C3449.8 (2)
C7—C8—C13—O64.7 (3)C12—C26—C33—C34169.90 (18)
C9—C8—C13—O6158.98 (19)C26—C33—C34—C35160.03 (18)
C7—C8—C13—C12173.66 (19)C33—C34—C35—C3694.7 (3)
C9—C8—C13—C1222.6 (3)C34—C35—C36—C384.3 (5)
C11—C12—C13—O6163.19 (18)C34—C35—C36—C37178.4 (2)
C19—C12—C13—O645.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1O···O4i0.841.942.7732 (19)171
O3A—H3O···O60.841.622.3934 (18)153
Symmetry code: (i) x+1/2, y1/2, z.
 

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