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Osajin [systematic name: 5-hydroxy-3-(3-hydroxy­phenyl)-8,8-di­methyl-6-(3-methyl­but-2-enyl)-4H,8H-pyrano­[2,3-h]­chro­men-4-one, C25H24O5, crystallizes with two independent mol­ecules in the asymmetric unit. The benzo­pyran­one ring system is nearly planar in both mol­ecules and they differ significantly only in the orientation of the benzene rings, which are rotated by 56.27 (7) and 44.16 (7)° with respect to the benzo­pyran­one systems. In the crystal structure, intermolecular O—H...O hydrogen bonds link the mol­ecules into dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805015667/cv6513sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805015667/cv6513Isup2.hkl
Contains datablock I

CCDC reference: 274385

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.049
  • wR factor = 0.125
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.85 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.71 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 5.57 su PLAT432_ALERT_2_C Short Inter X...Y Contact C22 .. C22 .. 3.15 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C22A .. C22A .. 3.18 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PARST (Nardelli, 1995).

5-hydroxy-3-(3-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)- 4H,8H-pyrano[2,3-h]chromen-4-one top
Crystal data top
C25H24O5Z = 4
Mr = 404.44F(000) = 856
Triclinic, P1Dx = 1.316 Mg m3
a = 8.8220 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.641 (2) ÅCell parameters from 2831 reflections
c = 21.504 (3) Åθ = 2.0–27.6°
α = 75.865 (11)°µ = 0.09 mm1
β = 87.731 (10)°T = 120 K
γ = 72.474 (12)°Prism, yellow
V = 2040.7 (5) Å30.50 × 0.50 × 0.40 mm
Data collection top
Kuma KM-4 + CCD
diffractometer
3734 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
Enhance (Oxford Diffraction) monochromatorθmax = 25.0°, θmin = 3.0°
Detector resolution: 16.3 pixels mm-1h = 1010
rotation method, ω–scank = 1113
14158 measured reflectionsl = 2525
7159 independent reflections
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.04P)2 + 0.01P]
where P = (Fo2 + 2Fc2)/3
7159 reflections(Δ/σ)max < 0.001
563 parametersΔρmax = 0.37 e Å3
4 restraintsΔρmin = 0.23 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
O10.5820 (2)0.78798 (16)0.31745 (8)0.0236 (5)
O20.1209 (2)0.82577 (17)0.36785 (9)0.0294 (5)
O30.5654 (2)0.50623 (16)0.19317 (8)0.0230 (5)
O40.1068 (2)0.67496 (18)0.30042 (9)0.0306 (5)
O50.1751 (2)1.07659 (18)0.59410 (9)0.0303 (5)
C10.5141 (3)0.8513 (2)0.36154 (12)0.0222 (7)
H10.57770.88860.37970.027*
C20.3660 (3)0.8663 (2)0.38189 (12)0.0195 (6)
C30.2648 (3)0.8122 (2)0.35430 (12)0.0222 (7)
C40.3407 (3)0.7356 (2)0.31079 (12)0.0202 (6)
C50.2607 (3)0.6654 (2)0.28614 (12)0.0220 (7)
C60.3369 (3)0.5877 (2)0.24726 (12)0.0195 (6)
C70.4936 (3)0.5845 (2)0.23124 (12)0.0199 (6)
C80.5789 (3)0.6506 (2)0.25416 (12)0.0210 (7)
C90.4988 (3)0.7241 (2)0.29441 (12)0.0194 (6)
C100.7445 (3)0.6317 (2)0.23727 (13)0.0239 (7)
H100.81200.66000.25920.029*
C110.8001 (3)0.5750 (2)0.19123 (13)0.0258 (7)
H110.90980.55770.18210.031*
C120.6924 (3)0.5376 (2)0.15327 (12)0.0241 (7)
C130.6141 (3)0.6421 (2)0.09523 (12)0.0294 (7)
H13A0.54160.61560.07250.044*
H13B0.69630.66170.06630.044*
H13C0.55430.71610.10970.044*
C140.7776 (3)0.4196 (2)0.13212 (13)0.0302 (7)
H14A0.82340.35230.16990.045*
H14B0.86260.43400.10340.045*
H14C0.70160.39630.10940.045*
C150.2525 (3)0.5158 (2)0.21955 (12)0.0230 (7)
H15A0.32830.43440.21770.028*
H15B0.16590.50020.24780.028*
C160.1841 (3)0.5854 (3)0.15323 (13)0.0244 (7)
H160.11540.66740.14970.029*
C170.2065 (3)0.5485 (3)0.09929 (14)0.0276 (7)
C180.3115 (4)0.4242 (3)0.09342 (16)0.0466 (9)
H18A0.36470.37710.13500.070*
H18B0.39150.43550.06150.070*
H18C0.24700.37860.07990.070*
C190.1247 (4)0.6312 (3)0.03732 (14)0.0446 (9)
H19A0.05880.71070.04470.067*
H19B0.05730.59110.02090.067*
H19C0.20460.64570.00590.067*
C200.3106 (3)0.9279 (2)0.43526 (12)0.0202 (6)
C210.1710 (3)1.0220 (2)0.43289 (13)0.0275 (7)
H210.10481.05140.39500.033*
C220.1235 (3)1.0756 (2)0.48440 (13)0.0266 (7)
H220.02831.14260.48110.032*
C230.2173 (3)1.0297 (2)0.54082 (13)0.0224 (6)
C240.3588 (3)0.9358 (2)0.54430 (13)0.0255 (7)
H240.42350.90560.58260.031*
C250.4066 (3)0.8855 (2)0.49203 (12)0.0252 (7)
H250.50500.82190.49450.030*
O1A1.0782 (2)0.29570 (16)0.31523 (8)0.0236 (5)
O2A0.6097 (2)0.35465 (17)0.35758 (8)0.0266 (5)
O3A1.0590 (2)0.00868 (16)0.19567 (8)0.0242 (5)
O4A0.5938 (2)0.19990 (17)0.29105 (9)0.0271 (5)
O5A0.6693 (2)0.62740 (17)0.57690 (9)0.0293 (5)
C1A1.0117 (3)0.3612 (2)0.35901 (12)0.0237 (7)
H1A1.07720.39550.37820.028*
C2A0.8596 (3)0.3810 (2)0.37722 (12)0.0221 (7)
C3A0.7561 (3)0.3311 (2)0.34743 (12)0.0198 (6)
C4A0.8315 (3)0.2511 (2)0.30627 (12)0.0193 (6)
C5A0.7508 (3)0.1836 (2)0.28104 (12)0.0198 (6)
C6A0.8282 (3)0.0999 (2)0.24535 (12)0.0210 (6)
C7A0.9866 (3)0.0907 (2)0.23099 (12)0.0202 (6)
C8A1.0717 (3)0.1565 (2)0.25355 (12)0.0190 (6)
C9A0.9912 (3)0.2346 (2)0.29172 (12)0.0208 (7)
C10A1.2409 (3)0.1314 (2)0.24010 (13)0.0259 (7)
H10A1.30850.15810.26300.031*
C11A1.2985 (3)0.0703 (3)0.19503 (13)0.0288 (7)
H11A1.40910.04940.18730.035*
C12A1.1903 (3)0.0343 (2)0.15643 (12)0.0234 (7)
C13A1.1181 (3)0.1389 (2)0.09727 (13)0.0304 (7)
H13D1.04210.11510.07480.046*
H13E1.20280.15320.06840.046*
H13F1.06310.21510.11070.046*
C14A1.2745 (3)0.0853 (2)0.13688 (14)0.0307 (7)
H14D1.31690.15190.17530.046*
H14E1.36200.07330.10910.046*
H14F1.19890.10800.11360.046*
C15A0.7421 (3)0.0256 (2)0.21950 (12)0.0249 (7)
H15C0.81650.05760.22000.030*
H15D0.65350.01410.24760.030*
C16A0.6774 (3)0.0898 (2)0.15209 (13)0.0236 (7)
H16A0.60720.17170.14660.028*
C17A0.7042 (3)0.0485 (3)0.09952 (14)0.0289 (7)
C18A0.8140 (4)0.0777 (3)0.09660 (16)0.0470 (9)
H18D0.86610.12100.13890.071*
H18E0.89490.06750.06490.071*
H18F0.75240.12640.08410.071*
C19A0.6231 (4)0.1275 (3)0.03614 (14)0.0471 (9)
H19D0.55630.20810.04190.071*
H19E0.55670.08540.02070.071*
H19F0.70360.14030.00470.071*
C20A0.8051 (3)0.4490 (2)0.42828 (12)0.0225 (7)
C21A0.7229 (3)0.4010 (3)0.47936 (12)0.0278 (7)
H21A0.69780.32670.48030.033*
C22A0.6764 (3)0.4598 (2)0.52926 (12)0.0272 (7)
H22A0.61970.42560.56370.033*
C23A0.7119 (3)0.5659 (2)0.52884 (12)0.0224 (6)
C24A0.7950 (3)0.6161 (2)0.47841 (13)0.0278 (7)
H24A0.81990.69020.47790.033*
C25A0.8411 (3)0.5571 (2)0.42870 (13)0.0265 (7)
H25A0.89820.59120.39450.032*
H4O0.079 (4)0.729 (2)0.3284 (12)0.063 (7)*
H4P0.577 (4)0.258 (2)0.3167 (12)0.063 (7)*
H5O0.0685 (19)1.124 (3)0.596 (2)0.104 (11)*
H5P0.601 (4)0.584 (3)0.5994 (17)0.104 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0215 (11)0.0316 (11)0.0229 (10)0.0126 (9)0.0011 (9)0.0108 (9)
O20.0203 (11)0.0399 (12)0.0328 (11)0.0097 (9)0.0061 (9)0.0176 (10)
O30.0236 (11)0.0215 (10)0.0240 (10)0.0058 (9)0.0032 (9)0.0076 (9)
O40.0226 (11)0.0442 (13)0.0336 (12)0.0147 (10)0.0081 (9)0.0204 (10)
O50.0313 (13)0.0395 (13)0.0255 (11)0.0112 (10)0.0054 (10)0.0180 (10)
C10.0281 (17)0.0236 (16)0.0180 (14)0.0086 (13)0.0001 (13)0.0096 (13)
C20.0237 (16)0.0215 (15)0.0154 (14)0.0096 (13)0.0019 (12)0.0042 (12)
C30.0228 (16)0.0235 (16)0.0162 (14)0.0053 (13)0.0006 (12)0.0008 (12)
C40.0257 (16)0.0197 (15)0.0138 (13)0.0059 (13)0.0008 (12)0.0027 (12)
C50.0217 (16)0.0281 (16)0.0175 (14)0.0117 (13)0.0008 (12)0.0025 (13)
C60.0226 (16)0.0202 (15)0.0160 (14)0.0078 (13)0.0016 (12)0.0025 (12)
C70.0235 (16)0.0178 (15)0.0141 (14)0.0032 (13)0.0002 (12)0.0004 (12)
C80.0222 (16)0.0242 (16)0.0158 (14)0.0074 (13)0.0005 (12)0.0026 (13)
C90.0185 (15)0.0242 (15)0.0162 (14)0.0098 (13)0.0029 (12)0.0017 (12)
C100.0181 (16)0.0308 (17)0.0241 (15)0.0091 (13)0.0013 (13)0.0065 (14)
C110.0170 (15)0.0326 (17)0.0268 (16)0.0057 (13)0.0016 (13)0.0076 (14)
C120.0254 (16)0.0241 (16)0.0192 (14)0.0041 (13)0.0055 (13)0.0039 (13)
C130.0347 (18)0.0265 (16)0.0230 (15)0.0051 (14)0.0040 (14)0.0041 (14)
C140.0281 (17)0.0298 (17)0.0273 (16)0.0015 (14)0.0028 (14)0.0063 (14)
C150.0206 (15)0.0243 (15)0.0257 (15)0.0078 (13)0.0055 (13)0.0087 (13)
C160.0216 (16)0.0243 (16)0.0294 (16)0.0084 (13)0.0015 (13)0.0087 (14)
C170.0312 (18)0.0287 (17)0.0276 (16)0.0116 (14)0.0013 (14)0.0124 (14)
C180.056 (2)0.042 (2)0.044 (2)0.0093 (18)0.0054 (18)0.0239 (17)
C190.055 (2)0.050 (2)0.0306 (18)0.0148 (18)0.0050 (17)0.0135 (17)
C200.0233 (16)0.0184 (15)0.0196 (14)0.0083 (13)0.0022 (12)0.0029 (12)
C210.0337 (17)0.0278 (16)0.0207 (15)0.0094 (14)0.0052 (13)0.0041 (13)
C220.0293 (16)0.0206 (15)0.0274 (16)0.0046 (13)0.0014 (13)0.0049 (13)
C230.0204 (15)0.0277 (16)0.0211 (15)0.0080 (13)0.0033 (12)0.0093 (13)
C240.0309 (16)0.0264 (16)0.0207 (14)0.0129 (13)0.0034 (13)0.0023 (13)
C250.0258 (16)0.0236 (15)0.0267 (15)0.0082 (13)0.0005 (13)0.0063 (13)
O1A0.0236 (11)0.0278 (11)0.0229 (10)0.0109 (9)0.0024 (9)0.0090 (9)
O2A0.0224 (11)0.0341 (11)0.0241 (10)0.0083 (9)0.0007 (9)0.0089 (9)
O3A0.0247 (11)0.0247 (11)0.0236 (10)0.0075 (9)0.0022 (9)0.0069 (9)
O4A0.0206 (11)0.0366 (12)0.0270 (11)0.0106 (10)0.0025 (9)0.0106 (10)
O5A0.0283 (12)0.0372 (12)0.0262 (11)0.0101 (10)0.0010 (9)0.0139 (10)
C1A0.0309 (18)0.0255 (16)0.0164 (14)0.0115 (14)0.0023 (13)0.0040 (13)
C2A0.0243 (16)0.0197 (15)0.0192 (14)0.0057 (13)0.0024 (13)0.0004 (12)
C3A0.0210 (16)0.0211 (15)0.0158 (14)0.0078 (13)0.0023 (12)0.0007 (12)
C4A0.0207 (16)0.0223 (15)0.0153 (14)0.0089 (13)0.0012 (12)0.0019 (12)
C5A0.0155 (15)0.0253 (15)0.0166 (14)0.0068 (12)0.0016 (12)0.0009 (12)
C6A0.0252 (16)0.0211 (15)0.0160 (14)0.0092 (13)0.0021 (12)0.0001 (12)
C7A0.0249 (16)0.0181 (15)0.0155 (14)0.0038 (13)0.0020 (13)0.0031 (12)
C8A0.0164 (15)0.0215 (15)0.0183 (14)0.0057 (12)0.0001 (12)0.0030 (13)
C9A0.0287 (17)0.0202 (15)0.0137 (14)0.0095 (13)0.0045 (13)0.0013 (12)
C10A0.0242 (17)0.0270 (16)0.0263 (16)0.0079 (14)0.0025 (14)0.0056 (14)
C11A0.0202 (16)0.0313 (17)0.0336 (17)0.0067 (14)0.0026 (14)0.0074 (15)
C12A0.0214 (16)0.0258 (16)0.0199 (15)0.0036 (13)0.0024 (13)0.0047 (13)
C13A0.0343 (18)0.0237 (16)0.0281 (16)0.0043 (14)0.0033 (14)0.0023 (14)
C14A0.0304 (18)0.0266 (16)0.0311 (17)0.0019 (14)0.0021 (14)0.0082 (14)
C15A0.0286 (16)0.0254 (16)0.0231 (15)0.0106 (13)0.0000 (13)0.0072 (13)
C16A0.0217 (16)0.0208 (15)0.0286 (16)0.0065 (13)0.0022 (13)0.0059 (13)
C17A0.0321 (18)0.0306 (17)0.0283 (17)0.0118 (15)0.0045 (14)0.0129 (15)
C18A0.058 (2)0.040 (2)0.047 (2)0.0102 (18)0.0026 (18)0.0224 (17)
C19A0.061 (2)0.054 (2)0.0301 (18)0.022 (2)0.0078 (17)0.0097 (17)
C20A0.0284 (17)0.0247 (15)0.0179 (14)0.0122 (13)0.0009 (13)0.0063 (13)
C21A0.0381 (18)0.0256 (16)0.0208 (15)0.0127 (14)0.0025 (13)0.0028 (13)
C22A0.0328 (17)0.0314 (17)0.0170 (14)0.0128 (14)0.0029 (13)0.0014 (13)
C23A0.0224 (15)0.0255 (16)0.0190 (14)0.0046 (13)0.0025 (12)0.0079 (13)
C24A0.0301 (17)0.0223 (15)0.0312 (16)0.0078 (13)0.0012 (13)0.0068 (13)
C25A0.0313 (16)0.0272 (16)0.0213 (14)0.0115 (13)0.0028 (13)0.0033 (13)
Geometric parameters (Å, º) top
O1—C11.353 (3)O1A—C1A1.359 (3)
O1—C91.369 (3)O1A—C9A1.373 (3)
O2—C31.262 (3)O2A—C3A1.259 (3)
O3—C71.370 (3)O3A—C7A1.359 (3)
O3—C121.463 (3)O3A—C12A1.466 (3)
O4—C51.358 (3)O4A—C5A1.357 (3)
O4—H4O0.946 (10)O4A—H4P0.953 (10)
O5—C231.378 (3)O5A—C23A1.375 (3)
O5—H5O0.94 (3)O5A—H5P0.95 (4)
C1—C21.336 (3)C1A—C2A1.350 (4)
C1—H10.9500C1A—H1A0.9500
C2—C31.452 (4)C2A—C3A1.459 (4)
C2—C201.489 (4)C2A—C20A1.489 (4)
C3—C41.455 (4)C3A—C4A1.441 (4)
C4—C91.400 (4)C4A—C9A1.397 (4)
C4—C51.426 (4)C4A—C5A1.412 (3)
C5—C61.389 (4)C5A—C6A1.388 (4)
C6—C71.403 (4)C6A—C7A1.398 (4)
C6—C151.505 (3)C6A—C15A1.516 (4)
C7—C81.401 (4)C7A—C8A1.394 (3)
C8—C91.390 (4)C8A—C9A1.391 (4)
C8—C101.455 (4)C8A—C10A1.463 (4)
C10—C111.320 (4)C10A—C11A1.336 (4)
C10—H100.9500C10A—H10A0.9500
C11—C121.498 (4)C11A—C12A1.500 (4)
C11—H110.9500C11A—H11A0.9500
C12—C141.522 (4)C12A—C14A1.519 (4)
C12—C131.528 (3)C12A—C13A1.532 (3)
C13—H13A0.9800C13A—H13D0.9800
C13—H13B0.9800C13A—H13E0.9800
C13—H13C0.9800C13A—H13F0.9800
C14—H14A0.9800C14A—H14D0.9800
C14—H14B0.9800C14A—H14E0.9800
C14—H14C0.9800C14A—H14F0.9800
C15—C161.505 (3)C15A—C16A1.505 (3)
C15—H15A0.9900C15A—H15C0.9900
C15—H15B0.9900C15A—H15D0.9900
C16—C171.321 (4)C16A—C17A1.319 (4)
C16—H160.9500C16A—H16A0.9500
C17—C181.497 (4)C17A—C18A1.511 (4)
C17—C191.502 (4)C17A—C19A1.511 (4)
C18—H18A0.9800C18A—H18D0.9800
C18—H18B0.9800C18A—H18E0.9800
C18—H18C0.9800C18A—H18F0.9800
C19—H19A0.9800C19A—H19D0.9800
C19—H19B0.9800C19A—H19E0.9800
C19—H19C0.9800C19A—H19F0.9800
C20—C211.373 (4)C20A—C21A1.388 (3)
C20—C251.410 (4)C20A—C25A1.389 (4)
C21—C221.391 (4)C21A—C22A1.394 (4)
C21—H210.9500C21A—H21A0.9500
C22—C231.392 (4)C22A—C23A1.361 (4)
C22—H220.9500C22A—H22A0.9500
C23—C241.380 (4)C23A—C24A1.393 (3)
C24—C251.385 (4)C24A—C25A1.392 (4)
C24—H240.9500C24A—H24A0.9500
C25—H250.9500C25A—H25A0.9500
C1—O1—C9118.5 (2)C1A—O1A—C9A118.6 (2)
C7—O3—C12116.7 (2)C7A—O3A—C12A117.0 (2)
C5—O4—H4O106 (2)C5A—O4A—H4P98 (2)
C23—O5—H5O118 (3)C23A—O5A—H5P100 (3)
C2—C1—O1126.1 (3)C2A—C1A—O1A124.9 (3)
C2—C1—H1117.0C2A—C1A—H1A117.6
O1—C1—H1117.0O1A—C1A—H1A117.6
C1—C2—C3118.3 (3)C1A—C2A—C3A118.5 (3)
C1—C2—C20120.7 (3)C1A—C2A—C20A119.1 (3)
C3—C2—C20120.8 (3)C3A—C2A—C20A122.4 (3)
O2—C3—C2123.5 (3)O2A—C3A—C4A121.5 (3)
O2—C3—C4120.6 (3)O2A—C3A—C2A122.3 (3)
C2—C3—C4115.9 (3)C4A—C3A—C2A116.1 (3)
C9—C4—C5117.9 (3)C9A—C4A—C5A117.5 (3)
C9—C4—C3120.3 (3)C9A—C4A—C3A120.3 (3)
C5—C4—C3121.7 (3)C5A—C4A—C3A122.2 (3)
O4—C5—C6119.0 (3)O4A—C5A—C6A118.2 (3)
O4—C5—C4119.7 (3)O4A—C5A—C4A120.2 (2)
C6—C5—C4121.3 (3)C6A—C5A—C4A121.6 (3)
C5—C6—C7117.4 (3)C5A—C6A—C7A117.8 (3)
C5—C6—C15121.8 (2)C5A—C6A—C15A121.5 (3)
C7—C6—C15120.7 (2)C7A—C6A—C15A120.6 (3)
O3—C7—C8120.1 (2)O3A—C7A—C8A120.3 (2)
O3—C7—C6115.8 (3)O3A—C7A—C6A116.5 (3)
C8—C7—C6124.0 (3)C8A—C7A—C6A123.1 (3)
C9—C8—C7116.2 (3)C9A—C8A—C7A116.8 (3)
C9—C8—C10125.5 (3)C9A—C8A—C10A124.7 (3)
C7—C8—C10118.2 (3)C7A—C8A—C10A118.3 (3)
O1—C9—C8116.5 (2)O1A—C9A—C8A116.1 (2)
O1—C9—C4120.4 (3)O1A—C9A—C4A120.9 (3)
C8—C9—C4123.1 (3)C8A—C9A—C4A123.0 (3)
C11—C10—C8119.5 (3)C11A—C10A—C8A118.7 (3)
C11—C10—H10120.2C11A—C10A—H10A120.7
C8—C10—H10120.2C8A—C10A—H10A120.7
C10—C11—C12120.8 (3)C10A—C11A—C12A120.7 (3)
C10—C11—H11119.6C10A—C11A—H11A119.7
C12—C11—H11119.6C12A—C11A—H11A119.7
O3—C12—C11110.3 (2)O3A—C12A—C11A109.7 (2)
O3—C12—C14104.3 (2)O3A—C12A—C14A105.4 (2)
C11—C12—C14112.3 (2)C11A—C12A—C14A111.8 (2)
O3—C12—C13107.7 (2)O3A—C12A—C13A107.8 (2)
C11—C12—C13111.7 (2)C11A—C12A—C13A111.4 (2)
C14—C12—C13110.2 (2)C14A—C12A—C13A110.4 (2)
C12—C13—H13A109.5C12A—C13A—H13D109.5
C12—C13—H13B109.5C12A—C13A—H13E109.5
H13A—C13—H13B109.5H13D—C13A—H13E109.5
C12—C13—H13C109.5C12A—C13A—H13F109.5
H13A—C13—H13C109.5H13D—C13A—H13F109.5
H13B—C13—H13C109.5H13E—C13A—H13F109.5
C12—C14—H14A109.5C12A—C14A—H14D109.5
C12—C14—H14B109.5C12A—C14A—H14E109.5
H14A—C14—H14B109.5H14D—C14A—H14E109.5
C12—C14—H14C109.5C12A—C14A—H14F109.5
H14A—C14—H14C109.5H14D—C14A—H14F109.5
H14B—C14—H14C109.5H14E—C14A—H14F109.5
C16—C15—C6111.2 (2)C16A—C15A—C6A111.4 (2)
C16—C15—H15A109.4C16A—C15A—H15C109.4
C6—C15—H15A109.4C6A—C15A—H15C109.4
C16—C15—H15B109.4C16A—C15A—H15D109.4
C6—C15—H15B109.4C6A—C15A—H15D109.4
H15A—C15—H15B108.0H15C—C15A—H15D108.0
C17—C16—C15128.9 (3)C17A—C16A—C15A129.3 (3)
C17—C16—H16115.5C17A—C16A—H16A115.4
C15—C16—H16115.5C15A—C16A—H16A115.4
C16—C17—C18124.7 (3)C16A—C17A—C18A124.5 (3)
C16—C17—C19121.3 (3)C16A—C17A—C19A120.9 (3)
C18—C17—C19114.0 (3)C18A—C17A—C19A114.6 (3)
C17—C18—H18A109.5C17A—C18A—H18D109.5
C17—C18—H18B109.5C17A—C18A—H18E109.5
H18A—C18—H18B109.5H18D—C18A—H18E109.5
C17—C18—H18C109.5C17A—C18A—H18F109.5
H18A—C18—H18C109.5H18D—C18A—H18F109.5
H18B—C18—H18C109.5H18E—C18A—H18F109.5
C17—C19—H19A109.5C17A—C19A—H19D109.5
C17—C19—H19B109.5C17A—C19A—H19E109.5
H19A—C19—H19B109.5H19D—C19A—H19E109.5
C17—C19—H19C109.5C17A—C19A—H19F109.5
H19A—C19—H19C109.5H19D—C19A—H19F109.5
H19B—C19—H19C109.5H19E—C19A—H19F109.5
C21—C20—C25118.1 (3)C21A—C20A—C25A117.9 (3)
C21—C20—C2124.0 (2)C21A—C20A—C2A119.9 (2)
C25—C20—C2117.8 (2)C25A—C20A—C2A122.1 (2)
C20—C21—C22121.9 (3)C20A—C21A—C22A121.2 (3)
C20—C21—H21119.1C20A—C21A—H21A119.4
C22—C21—H21119.1C22A—C21A—H21A119.4
C21—C22—C23119.2 (3)C23A—C22A—C21A120.2 (3)
C21—C22—H22120.4C23A—C22A—H22A119.9
C23—C22—H22120.4C21A—C22A—H22A119.9
O5—C23—C24117.8 (2)C22A—C23A—O5A122.6 (2)
O5—C23—C22122.1 (3)C22A—C23A—C24A120.0 (3)
C24—C23—C22120.1 (3)O5A—C23A—C24A117.4 (2)
C23—C24—C25120.1 (3)C25A—C24A—C23A119.6 (3)
C23—C24—H24120.0C25A—C24A—H24A120.2
C25—C24—H24120.0C23A—C24A—H24A120.2
C24—C25—C20120.6 (3)C20A—C25A—C24A121.1 (3)
C24—C25—H25119.7C20A—C25A—H25A119.4
C20—C25—H25119.7C24A—C25A—H25A119.4
C13—C12—C11—C1087.8 (3)C13A—C12A—C11A—C10A87.1 (3)
C14—C12—C11—C10147.8 (3)C14A—C12A—C11A—C10A148.7 (3)
O2—C3—C4—C55.2 (4)O2A—C3A—C4A—C5A7.4 (4)
H4O—O4—C5—C43 (2)H4P—O4A—C5A—C4A1.7 (19)
C5—C6—C15—C1694.0 (3)C5A—C6A—C15A—C16A93.5 (3)
C6—C15—C16—C17125.1 (3)C6A—C15A—C16A—C17A122.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4O···O20.95 (1)1.70 (2)2.567 (3)151 (3)
O4A—H4P···O2A0.95 (1)1.68 (3)2.596 (3)162 (3)
O5—H5O···O2i0.94 (3)1.81 (2)2.698 (3)157 (4)
O5A—H5P···O2Aii0.95 (4)2.05 (3)2.765 (3)131 (3)
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+1, z+1.
 

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