Download citation
Download citation
link to html
The title compound, C10H10O2, was isolated from Eniconsanthum membranifolium J. Sinclair. There are six independent mol­ecules in the unit cell. Intra­molecular hydrogen bonds from the hydr­oxy H atoms to the carbonyl O atoms are observed in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015418/dn2030sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015418/dn2030Isup2.hkl
Contains datablock I

CCDC reference: 610755

Key indicators

  • Single-crystal X-ray study
  • T = 118 K
  • Mean [sigma](C-C) = 0.011 Å
  • R factor = 0.098
  • wR factor = 0.211
  • Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 11
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.94 PLAT230_ALERT_2_C Hirshfeld Test Diff for C7F - C8F .. 5.49 su
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 27.48 From the CIF: _reflns_number_total 5676 Count of symmetry unique reflns 5756 Completeness (_total/calc) 98.61% 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
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Rigaku/MSC, 2004); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and TEXSAN.

(R)-(-)-8-Hydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one top
Crystal data top
C10H10O3Z = 6
Mr = 178.19F(000) = 564
Triclinic, P1Dx = 1.409 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.375 (8) ÅCell parameters from 2855 reflections
b = 10.826 (11) Åθ = 3.0–27.5°
c = 15.321 (14) ŵ = 0.10 mm1
α = 70.80 (4)°T = 118 K
β = 75.25 (5)°Block, colourless
γ = 79.05 (5)°0.40 × 0.10 × 0.10 mm
V = 1260 (2) Å3
Data collection top
Rigaku/MSC Mercury CCD area-detector
diffractometer
Rint = 0.061
Detector resolution: 14.62 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scansh = 1010
10247 measured reflectionsk = 1214
5676 independent reflectionsl = 1916
4555 reflections with I > 2σ(I)
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)] = 0.098Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.211H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0535P)2 + 2.6686P]
where P = (Fo2 + 2Fc2)/3
5676 reflections(Δ/σ)max = 0.001
715 parametersΔρmax = 0.37 e Å3
3 restraintsΔρmin = 0.36 e Å3
Special details top

Experimental. 1H NMR (400 MHz, CDCl3, δ, p.p.m.): 11.0 (1H, s), 7.41 (1H, J = 8.0 Hz), 6.89 (1H, d, J = 8.0 Hz), 6.69 (1H, d, J = 8.0 Hz), 4.73 (1H, m), 2.93 (2H, d, J = 7.4 Hz), 1.53 (3H, d, J = 6.3 Hz); 13C NMR (100 MHz, CDCl3, δ, p.p.m.): 170.0, 162.3, 139.5, 136.3, 118.0, 116.4, 108.4, 76.9, 34.8, 20.9.

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
C1A0.8416 (9)0.8257 (7)0.7190 (5)0.0230 (15)
O1A0.9527 (6)0.8180 (6)0.7614 (4)0.0307 (12)
O2A0.6870 (6)0.8314 (5)0.7666 (4)0.0278 (12)
C2A0.5520 (8)0.8722 (8)0.7133 (5)0.0254 (15)
H1A0.54810.96880.68010.030*
C3A0.5797 (9)0.7994 (8)0.6423 (5)0.0262 (16)
H2A0.49650.83610.60180.031*
H3A0.56570.70540.67500.031*
C4A0.7506 (9)0.8110 (7)0.5825 (5)0.0229 (15)
C5A0.7883 (9)0.8047 (8)0.4912 (5)0.0284 (16)
H4A0.70320.79530.46380.034*
C6A0.9500 (10)0.8121 (8)0.4386 (6)0.0302 (17)
H5A0.97320.80990.37510.036*
C7A1.0752 (9)0.8224 (8)0.4762 (5)0.0293 (17)
H6A1.18570.82440.44000.035*
C8A1.0411 (9)0.8299 (7)0.5676 (5)0.0270 (16)
C9A0.8769 (8)0.8237 (7)0.6209 (5)0.0205 (14)
O3A1.1682 (6)0.8352 (6)0.6049 (4)0.0291 (12)
H7A1.13530.82350.66330.044*
C10A0.3960 (10)0.8459 (8)0.7872 (6)0.0338 (18)
H8A0.40280.75230.82300.051*
H9A0.30030.86940.75670.051*
H10A0.38300.89890.83010.051*
C1B0.3221 (9)0.4870 (8)0.7595 (5)0.0276 (16)
O1B0.3444 (7)0.5008 (7)0.8314 (4)0.0385 (14)
O2B0.4556 (6)0.4714 (5)0.6936 (4)0.0300 (12)
C2B0.4391 (8)0.4317 (8)0.6140 (5)0.0254 (16)
H1B0.42560.33570.63600.031*
C3B0.2906 (8)0.5081 (8)0.5766 (5)0.0262 (16)
H2B0.30930.60190.54770.031*
H3B0.27470.47490.52680.031*
C4B0.1389 (8)0.4972 (7)0.6526 (5)0.0235 (15)
C5B0.0175 (8)0.4968 (7)0.6393 (5)0.0227 (15)
H4B0.03220.49950.57920.027*
C6B0.1534 (10)0.4925 (8)0.7137 (7)0.0348 (19)
H5B0.26080.49280.70360.042*
C7B0.1369 (10)0.4878 (7)0.8008 (6)0.0296 (17)
H6B0.23200.48500.85070.035*
C8B0.0212 (9)0.4871 (8)0.8168 (5)0.0262 (16)
C9B0.1587 (9)0.4910 (7)0.7420 (5)0.0236 (15)
O3B0.0328 (7)0.4861 (6)0.9030 (4)0.0351 (14)
H7B0.12860.50140.90090.053*
C10B0.6019 (8)0.4532 (9)0.5442 (6)0.0302 (18)
H8B0.61780.54660.52410.045*
H9B0.60070.42670.48910.045*
H10B0.69320.40040.57410.045*
C1C0.9241 (10)0.1462 (8)0.8723 (5)0.0282 (17)
O1C1.0334 (7)0.1312 (6)0.9156 (4)0.0370 (14)
O2C0.7649 (6)0.1569 (5)0.9199 (4)0.0273 (11)
C2C0.6306 (9)0.2012 (8)0.8681 (5)0.0280 (16)
H1C0.62690.29820.83650.034*
C3C0.6584 (9)0.1304 (8)0.7949 (6)0.0311 (17)
H2C0.64760.03570.82670.037*
H3C0.57270.16650.75610.037*
C4C0.8276 (9)0.1457 (8)0.7324 (5)0.0271 (16)
C5C0.8628 (9)0.1499 (8)0.6380 (5)0.0281 (16)
H4C0.77600.14760.60920.034*
C6C1.0231 (10)0.1574 (8)0.5859 (5)0.0318 (18)
H5C1.04610.15990.52140.038*
C7C1.1503 (10)0.1612 (8)0.6266 (6)0.0334 (18)
H6C1.26030.16620.58990.040*
C8C1.1198 (10)0.1579 (7)0.7197 (6)0.0303 (17)
C9C0.9537 (9)0.1524 (7)0.7741 (5)0.0226 (14)
O3C1.2467 (6)0.1594 (6)0.7591 (4)0.0334 (13)
H7C1.21150.14970.81710.050*
C10C0.4736 (10)0.1719 (9)0.9418 (6)0.040 (2)
H8C0.47360.07640.96930.060*
H9C0.37700.20870.91250.060*
H10C0.46820.21160.99160.060*
C1D0.7940 (9)0.7687 (7)0.1912 (5)0.0242 (15)
O1D0.8214 (7)0.7741 (6)0.2657 (4)0.0345 (13)
O2D0.9274 (6)0.7636 (5)0.1232 (4)0.0262 (11)
C2D0.9077 (9)0.7306 (8)0.0392 (5)0.0272 (16)
H1D0.89770.63440.05690.033*
C3D0.7561 (8)0.8088 (8)0.0046 (5)0.0256 (15)
H2D0.73760.77860.04610.031*
H3D0.77310.90300.02210.031*
C4D0.6054 (9)0.7924 (7)0.0847 (5)0.0240 (15)
C5D0.4483 (10)0.7966 (8)0.0706 (6)0.0322 (18)
H4D0.43210.80560.00960.039*
C6D0.3141 (9)0.7878 (9)0.1461 (6)0.0344 (19)
H5D0.20540.79240.13620.041*
C7D0.3355 (9)0.7724 (8)0.2347 (6)0.0297 (17)
H6D0.24170.76610.28550.036*
C8D0.4926 (10)0.7658 (8)0.2510 (5)0.0298 (17)
C9D0.6281 (9)0.7740 (7)0.1758 (5)0.0239 (15)
O3D0.5076 (7)0.7484 (6)0.3398 (4)0.0348 (13)
H7D0.60540.75650.33960.052*
C10D1.0674 (9)0.7603 (9)0.0298 (6)0.0336 (18)
H8D1.08830.84960.03720.050*
H9D1.06020.75380.09090.050*
H10D1.15860.69690.00640.050*
C1E0.3962 (9)0.4345 (7)0.3113 (6)0.0279 (16)
O1E0.5069 (6)0.4172 (6)0.3536 (4)0.0308 (12)
O2E0.2386 (6)0.4433 (5)0.3591 (4)0.0306 (12)
C2E0.1056 (8)0.4906 (8)0.3061 (5)0.0253 (16)
H1E0.10740.58710.27350.030*
C3E0.1316 (8)0.4189 (8)0.2331 (5)0.0242 (15)
H2E0.12270.32400.26490.029*
H3E0.04480.45420.19490.029*
C4E0.2986 (9)0.4366 (7)0.1706 (5)0.0241 (15)
C5E0.3324 (10)0.4480 (8)0.0740 (5)0.0318 (18)
H4E0.24660.44430.04490.038*
C6E0.4920 (9)0.4645 (8)0.0217 (6)0.0304 (18)
H5E0.51300.47640.04430.037*
C7E0.6219 (9)0.4644 (8)0.0622 (6)0.0282 (16)
H6E0.73130.47290.02520.034*
C8E0.5891 (8)0.4516 (7)0.1574 (5)0.0239 (15)
C9E0.4286 (9)0.4417 (7)0.2117 (5)0.0235 (15)
O3E0.7186 (6)0.4511 (6)0.1963 (4)0.0274 (12)
H7E0.68710.43260.25530.041*
C10E0.0540 (10)0.4686 (8)0.3773 (6)0.0333 (18)
H8E0.05070.37570.41480.050*
H9E0.14700.49220.34460.050*
H10E0.06900.52360.41910.050*
C1F0.8426 (9)0.1339 (8)0.3379 (5)0.0274 (16)
O1F0.8620 (6)0.1576 (6)0.4066 (4)0.0312 (12)
O2F0.9746 (6)0.1292 (6)0.2686 (4)0.0291 (12)
C2F0.9683 (9)0.0788 (8)0.1933 (5)0.0265 (16)
H1F0.97580.01940.21740.032*
C3F0.8076 (9)0.1319 (7)0.1588 (5)0.0255 (16)
H2F0.80710.22730.12550.031*
H3F0.79880.08710.11360.031*
C4F0.6618 (8)0.1098 (7)0.2404 (5)0.0237 (15)
C5F0.5110 (9)0.0902 (9)0.2305 (6)0.0332 (18)
H4F0.49650.08870.17140.040*
C6F0.3797 (10)0.0725 (8)0.3088 (6)0.0324 (18)
H5F0.27580.05740.30230.039*
C7F0.3952 (8)0.0761 (7)0.3944 (6)0.0279 (17)
H6F0.30340.06380.44660.034*
C8F0.5469 (10)0.0981 (8)0.4044 (5)0.0315 (18)
C9F0.6824 (9)0.1145 (7)0.3274 (5)0.0221 (14)
O3F0.5619 (7)0.1072 (6)0.4884 (4)0.0339 (13)
H7F0.65220.13590.48140.051*
C10F1.1203 (9)0.1177 (9)0.1175 (6)0.0349 (19)
H8F1.11300.21390.09270.052*
H9F1.12670.08050.06620.052*
H10F1.22000.08390.14440.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.031 (4)0.019 (3)0.020 (3)0.005 (3)0.002 (3)0.009 (3)
O1A0.029 (3)0.038 (3)0.028 (3)0.001 (2)0.010 (2)0.013 (2)
O2A0.024 (3)0.034 (3)0.025 (3)0.002 (2)0.002 (2)0.014 (2)
C2A0.025 (3)0.030 (4)0.025 (4)0.004 (3)0.007 (3)0.011 (3)
C3A0.019 (3)0.038 (4)0.021 (4)0.005 (3)0.001 (3)0.011 (3)
C4A0.037 (4)0.020 (4)0.016 (3)0.006 (3)0.007 (3)0.008 (3)
C5A0.027 (4)0.033 (4)0.029 (4)0.001 (3)0.008 (3)0.014 (3)
C6A0.035 (4)0.026 (4)0.024 (4)0.001 (3)0.002 (3)0.007 (3)
C7A0.023 (3)0.033 (4)0.021 (4)0.002 (3)0.002 (3)0.002 (3)
C8A0.026 (4)0.024 (4)0.031 (4)0.001 (3)0.002 (3)0.013 (3)
C9A0.024 (3)0.024 (3)0.017 (3)0.005 (3)0.006 (3)0.007 (3)
O3A0.022 (3)0.041 (3)0.026 (3)0.004 (2)0.003 (2)0.013 (3)
C10A0.031 (4)0.037 (5)0.031 (4)0.005 (3)0.003 (3)0.014 (4)
C1B0.026 (4)0.037 (4)0.019 (4)0.008 (3)0.001 (3)0.009 (3)
O1B0.033 (3)0.061 (4)0.036 (3)0.008 (3)0.010 (2)0.029 (3)
O2B0.024 (3)0.038 (3)0.032 (3)0.004 (2)0.003 (2)0.017 (3)
C2B0.022 (3)0.037 (4)0.018 (3)0.001 (3)0.003 (3)0.016 (3)
C3B0.018 (3)0.040 (4)0.018 (3)0.002 (3)0.003 (3)0.011 (3)
C4B0.018 (3)0.030 (4)0.022 (4)0.004 (3)0.005 (3)0.011 (3)
C5B0.019 (3)0.025 (4)0.025 (4)0.006 (3)0.003 (3)0.009 (3)
C6B0.030 (4)0.029 (4)0.046 (5)0.001 (3)0.011 (4)0.011 (4)
C7B0.031 (4)0.023 (4)0.033 (4)0.001 (3)0.004 (3)0.014 (3)
C8B0.023 (4)0.046 (5)0.013 (3)0.005 (3)0.004 (3)0.013 (3)
C9B0.020 (3)0.022 (3)0.027 (4)0.001 (3)0.003 (3)0.008 (3)
O3B0.034 (3)0.051 (4)0.023 (3)0.011 (3)0.006 (2)0.019 (3)
C10B0.011 (3)0.055 (5)0.028 (4)0.007 (3)0.001 (3)0.018 (4)
C1C0.045 (5)0.026 (4)0.017 (3)0.005 (3)0.011 (3)0.007 (3)
O1C0.042 (3)0.047 (4)0.028 (3)0.008 (3)0.010 (3)0.015 (3)
O2C0.028 (3)0.034 (3)0.022 (3)0.002 (2)0.006 (2)0.011 (2)
C2C0.030 (4)0.029 (4)0.026 (4)0.002 (3)0.002 (3)0.013 (3)
C3C0.031 (4)0.030 (4)0.030 (4)0.002 (3)0.001 (3)0.009 (3)
C4C0.022 (4)0.033 (4)0.026 (4)0.000 (3)0.005 (3)0.012 (3)
C5C0.035 (4)0.034 (4)0.022 (4)0.005 (3)0.008 (3)0.014 (3)
C6C0.035 (4)0.037 (4)0.021 (4)0.000 (3)0.004 (3)0.014 (3)
C7C0.032 (4)0.041 (5)0.029 (4)0.001 (3)0.001 (3)0.018 (4)
C8C0.031 (4)0.021 (4)0.036 (4)0.000 (3)0.006 (3)0.007 (3)
C9C0.021 (3)0.020 (3)0.027 (4)0.001 (3)0.007 (3)0.006 (3)
O3C0.023 (3)0.034 (3)0.042 (3)0.001 (2)0.007 (2)0.011 (3)
C10C0.030 (4)0.052 (6)0.031 (4)0.010 (4)0.009 (3)0.012 (4)
C1D0.028 (4)0.028 (4)0.023 (4)0.005 (3)0.006 (3)0.014 (3)
O1D0.037 (3)0.040 (3)0.028 (3)0.003 (3)0.009 (2)0.011 (3)
O2D0.017 (2)0.042 (3)0.023 (3)0.009 (2)0.001 (2)0.014 (2)
C2D0.025 (4)0.030 (4)0.025 (4)0.010 (3)0.000 (3)0.006 (3)
C3D0.018 (3)0.033 (4)0.024 (4)0.007 (3)0.000 (3)0.006 (3)
C4D0.023 (3)0.030 (4)0.021 (3)0.009 (3)0.006 (3)0.007 (3)
C5D0.040 (4)0.030 (4)0.031 (4)0.002 (3)0.018 (3)0.008 (3)
C6D0.018 (4)0.048 (5)0.037 (5)0.002 (3)0.000 (3)0.019 (4)
C7D0.015 (3)0.043 (5)0.030 (4)0.009 (3)0.011 (3)0.018 (4)
C8D0.030 (4)0.033 (4)0.024 (4)0.006 (3)0.001 (3)0.010 (3)
C9D0.027 (4)0.027 (4)0.015 (3)0.005 (3)0.001 (3)0.004 (3)
O3D0.037 (3)0.045 (4)0.021 (3)0.007 (3)0.000 (2)0.013 (3)
C10D0.028 (4)0.038 (5)0.029 (4)0.008 (3)0.010 (3)0.002 (3)
C1E0.032 (4)0.022 (4)0.030 (4)0.005 (3)0.005 (3)0.009 (3)
O1E0.023 (3)0.047 (3)0.027 (3)0.003 (2)0.006 (2)0.017 (3)
O2E0.030 (3)0.034 (3)0.030 (3)0.006 (2)0.004 (2)0.012 (2)
C2E0.017 (3)0.032 (4)0.022 (4)0.007 (3)0.003 (3)0.004 (3)
C3E0.022 (3)0.032 (4)0.022 (4)0.002 (3)0.007 (3)0.012 (3)
C4E0.028 (4)0.023 (4)0.021 (4)0.005 (3)0.004 (3)0.005 (3)
C5E0.031 (4)0.043 (5)0.021 (4)0.005 (3)0.001 (3)0.015 (4)
C6E0.023 (4)0.044 (5)0.028 (4)0.003 (3)0.007 (3)0.018 (4)
C7E0.024 (3)0.029 (4)0.028 (4)0.001 (3)0.001 (3)0.010 (3)
C8E0.017 (3)0.032 (4)0.023 (4)0.003 (3)0.002 (3)0.013 (3)
C9E0.027 (4)0.028 (4)0.020 (4)0.005 (3)0.007 (3)0.011 (3)
O3E0.021 (2)0.042 (3)0.025 (3)0.003 (2)0.009 (2)0.014 (2)
C10E0.038 (5)0.028 (4)0.027 (4)0.001 (3)0.002 (3)0.005 (3)
C1F0.027 (4)0.026 (4)0.030 (4)0.006 (3)0.004 (3)0.009 (3)
O1F0.032 (3)0.041 (3)0.026 (3)0.005 (2)0.007 (2)0.017 (3)
O2F0.023 (3)0.038 (3)0.026 (3)0.008 (2)0.003 (2)0.007 (2)
C2F0.033 (4)0.029 (4)0.021 (4)0.000 (3)0.011 (3)0.011 (3)
C3F0.038 (4)0.023 (4)0.015 (3)0.001 (3)0.007 (3)0.005 (3)
C4F0.016 (3)0.029 (4)0.028 (4)0.005 (3)0.001 (3)0.014 (3)
C5F0.020 (4)0.053 (5)0.035 (4)0.003 (3)0.009 (3)0.021 (4)
C6F0.028 (4)0.040 (5)0.036 (4)0.002 (3)0.012 (3)0.020 (4)
C7F0.014 (3)0.031 (4)0.032 (4)0.005 (3)0.005 (3)0.007 (3)
C8F0.038 (4)0.027 (4)0.019 (4)0.003 (3)0.007 (3)0.008 (3)
C9F0.026 (3)0.021 (4)0.020 (3)0.004 (3)0.004 (3)0.006 (3)
O3F0.031 (3)0.051 (4)0.022 (3)0.006 (3)0.002 (2)0.019 (3)
C10F0.020 (4)0.054 (5)0.025 (4)0.012 (3)0.010 (3)0.012 (4)
Geometric parameters (Å, º) top
C1A—O1A1.239 (9)C1D—O1D1.241 (9)
C1A—O2A1.315 (8)C1D—O2D1.327 (8)
C1A—C9A1.463 (9)C1D—C9D1.455 (10)
O2A—C2A1.477 (9)O2D—C2D1.498 (9)
C2A—C3A1.492 (10)C2D—C10D1.493 (10)
C2A—C10A1.498 (10)C2D—C3D1.500 (10)
C2A—H1A1.0000C2D—H1D1.0000
C3A—C4A1.493 (10)C3D—C4D1.511 (9)
C3A—H2A0.9900C3D—H2D0.9900
C3A—H3A0.9900C3D—H3D0.9900
C4A—C5A1.375 (10)C4D—C5D1.376 (10)
C4A—C9A1.382 (10)C4D—C9D1.402 (10)
C5A—C6A1.390 (11)C5D—C6D1.384 (11)
C5A—H4A0.9500C5D—H4D0.9500
C6A—C7A1.356 (12)C6D—C7D1.365 (12)
C6A—H5A0.9500C6D—H5D0.9500
C7A—C8A1.383 (11)C7D—C8D1.386 (11)
C7A—H6A0.9500C7D—H6D0.9500
C8A—O3A1.348 (9)C8D—O3D1.346 (10)
C8A—C9A1.410 (10)C8D—C9D1.388 (9)
O3A—H7A0.8400O3D—H7D0.8400
C10A—H8A0.9800C10D—H8D0.9800
C10A—H9A0.9800C10D—H9D0.9800
C10A—H10A0.9800C10D—H10D0.9800
C1B—O1B1.223 (9)C1E—O1E1.215 (9)
C1B—O2B1.328 (8)C1E—O2E1.339 (9)
C1B—C9B1.451 (10)C1E—C9E1.459 (10)
O2B—C2B1.465 (9)O2E—C2E1.460 (9)
C2B—C3B1.490 (10)C2E—C10E1.497 (10)
C2B—C10B1.507 (9)C2E—C3E1.511 (10)
C2B—H1B1.0000C2E—H1E1.0000
C3B—C4B1.482 (9)C3E—C4E1.486 (10)
C3B—H2B0.9900C3E—H2E0.9900
C3B—H3B0.9900C3E—H3E0.9900
C4B—C5B1.377 (10)C4E—C5E1.402 (10)
C4B—C9B1.399 (10)C4E—C9E1.407 (11)
C5B—C6B1.387 (11)C5E—C6E1.383 (10)
C5B—H4B0.9500C5E—H4E0.9500
C6B—C7B1.361 (12)C6E—C7E1.383 (11)
C6B—H5B0.9500C6E—H5E0.9500
C7B—C8B1.405 (11)C7E—C8E1.378 (11)
C7B—H6B0.9500C7E—H6E0.9500
C8B—O3B1.345 (9)C8E—O3E1.363 (9)
C8B—C9B1.399 (9)C8E—C9E1.392 (9)
O3B—H7B0.8400O3E—H7E0.8400
C10B—H8B0.9800C10E—H8E0.9800
C10B—H9B0.9800C10E—H9E0.9800
C10B—H10B0.9800C10E—H10E0.9800
C1C—O1C1.219 (10)C1F—O1F1.217 (9)
C1C—O2C1.351 (9)C1F—O2F1.330 (9)
C1C—C9C1.443 (10)C1F—C9F1.452 (10)
O2C—C2C1.458 (9)O2F—C2F1.444 (9)
C2C—C3C1.504 (10)C2F—C10F1.508 (10)
C2C—C10C1.507 (10)C2F—C3F1.514 (10)
C2C—H1C1.0000C2F—H1F1.0000
C3C—C4C1.499 (10)C3F—C4F1.499 (10)
C3C—H2C0.9900C3F—H2F0.9900
C3C—H3C0.9900C3F—H3F0.9900
C4C—C5C1.387 (10)C4F—C5F1.372 (10)
C4C—C9C1.389 (10)C4F—C9F1.406 (10)
C5C—C6C1.378 (10)C5F—C6F1.393 (11)
C5C—H4C0.9500C5F—H4F0.9500
C6C—C7C1.378 (12)C6F—C7F1.365 (11)
C6C—H5C0.9500C6F—H5F0.9500
C7C—C8C1.374 (11)C7F—C8F1.390 (11)
C7C—H6C0.9500C7F—H6F0.9500
C8C—O3C1.354 (10)C8F—O3F1.362 (10)
C8C—C9C1.429 (10)C8F—C9F1.402 (9)
O3C—H7C0.8400O3F—H7F0.8400
C10C—H8C0.9800C10F—H8F0.9800
C10C—H9C0.9800C10F—H9F0.9800
C10C—H10C0.9800C10F—H10F0.9800
O1A—C1A—O2A117.5 (6)O1D—C1D—O2D115.3 (7)
O1A—C1A—C9A122.7 (7)O1D—C1D—C9D123.5 (7)
O2A—C1A—C9A119.8 (7)O2D—C1D—C9D121.1 (6)
C1A—O2A—C2A118.4 (6)C1D—O2D—C2D117.8 (5)
O2A—C2A—C3A110.8 (6)C10D—C2D—O2D103.4 (6)
O2A—C2A—C10A104.8 (6)C10D—C2D—C3D114.2 (6)
C3A—C2A—C10A113.5 (6)O2D—C2D—C3D110.6 (6)
O2A—C2A—H1A109.2C10D—C2D—H1D109.5
C3A—C2A—H1A109.2O2D—C2D—H1D109.5
C10A—C2A—H1A109.2C3D—C2D—H1D109.5
C2A—C3A—C4A110.1 (6)C2D—C3D—C4D110.4 (6)
C2A—C3A—H2A109.6C2D—C3D—H2D109.6
C4A—C3A—H2A109.6C4D—C3D—H2D109.6
C2A—C3A—H3A109.6C2D—C3D—H3D109.6
C4A—C3A—H3A109.6C4D—C3D—H3D109.6
H2A—C3A—H3A108.2H2D—C3D—H3D108.1
C5A—C4A—C9A118.6 (7)C5D—C4D—C9D119.6 (7)
C5A—C4A—C3A122.2 (7)C5D—C4D—C3D122.3 (7)
C9A—C4A—C3A119.2 (6)C9D—C4D—C3D118.1 (6)
C4A—C5A—C6A120.5 (7)C4D—C5D—C6D119.5 (8)
C4A—C5A—H4A119.8C4D—C5D—H4D120.3
C6A—C5A—H4A119.8C6D—C5D—H4D120.3
C7A—C6A—C5A121.3 (7)C7D—C6D—C5D121.1 (7)
C7A—C6A—H5A119.3C7D—C6D—H5D119.5
C5A—C6A—H5A119.3C5D—C6D—H5D119.5
C6A—C7A—C8A119.6 (7)C6D—C7D—C8D120.6 (6)
C6A—C7A—H6A120.2C6D—C7D—H6D119.7
C8A—C7A—H6A120.2C8D—C7D—H6D119.7
O3A—C8A—C7A118.7 (7)O3D—C8D—C7D118.4 (7)
O3A—C8A—C9A122.0 (7)O3D—C8D—C9D122.8 (7)
C7A—C8A—C9A119.3 (7)C7D—C8D—C9D118.8 (7)
C4A—C9A—C8A120.7 (7)C8D—C9D—C4D120.5 (7)
C4A—C9A—C1A119.8 (6)C8D—C9D—C1D119.7 (7)
C8A—C9A—C1A119.4 (7)C4D—C9D—C1D119.8 (6)
C8A—O3A—H7A109.5C8D—O3D—H7D109.5
C2A—C10A—H8A109.5C2D—C10D—H8D109.5
C2A—C10A—H9A109.5C2D—C10D—H9D109.5
H8A—C10A—H9A109.5H8D—C10D—H9D109.5
C2A—C10A—H10A109.5C2D—C10D—H10D109.5
H8A—C10A—H10A109.5H8D—C10D—H10D109.5
H9A—C10A—H10A109.5H9D—C10D—H10D109.5
O1B—C1B—O2B117.5 (7)O1E—C1E—O2E118.4 (7)
O1B—C1B—C9B123.4 (7)O1E—C1E—C9E122.5 (7)
O2B—C1B—C9B119.1 (7)O2E—C1E—C9E119.0 (7)
C1B—O2B—C2B119.6 (6)C1E—O2E—C2E118.7 (6)
O2B—C2B—C3B110.1 (6)O2E—C2E—C10E106.4 (6)
O2B—C2B—C10B104.9 (6)O2E—C2E—C3E109.7 (6)
C3B—C2B—C10B114.4 (6)C10E—C2E—C3E113.1 (7)
O2B—C2B—H1B109.1O2E—C2E—H1E109.2
C3B—C2B—H1B109.1C10E—C2E—H1E109.2
C10B—C2B—H1B109.1C3E—C2E—H1E109.2
C4B—C3B—C2B111.2 (6)C4E—C3E—C2E109.5 (6)
C4B—C3B—H2B109.4C4E—C3E—H2E109.8
C2B—C3B—H2B109.4C2E—C3E—H2E109.8
C4B—C3B—H3B109.4C4E—C3E—H3E109.8
C2B—C3B—H3B109.4C2E—C3E—H3E109.8
H2B—C3B—H3B108.0H2E—C3E—H3E108.2
C5B—C4B—C9B119.3 (6)C5E—C4E—C9E119.0 (7)
C5B—C4B—C3B124.0 (7)C5E—C4E—C3E123.5 (7)
C9B—C4B—C3B116.7 (6)C9E—C4E—C3E117.5 (6)
C4B—C5B—C6B119.9 (7)C6E—C5E—C4E119.2 (8)
C4B—C5B—H4B120.1C6E—C5E—H4E120.4
C6B—C5B—H4B120.1C4E—C5E—H4E120.4
C7B—C6B—C5B121.7 (8)C7E—C6E—C5E122.2 (8)
C7B—C6B—H5B119.2C7E—C6E—H5E118.9
C5B—C6B—H5B119.2C5E—C6E—H5E118.9
C6B—C7B—C8B119.8 (7)C8E—C7E—C6E118.6 (7)
C6B—C7B—H6B120.1C8E—C7E—H6E120.7
C8B—C7B—H6B120.1C6E—C7E—H6E120.7
O3B—C8B—C9B122.9 (7)O3E—C8E—C7E117.8 (6)
O3B—C8B—C7B118.3 (6)O3E—C8E—C9E121.0 (6)
C9B—C8B—C7B118.7 (6)C7E—C8E—C9E121.1 (7)
C4B—C9B—C8B120.7 (6)C8E—C9E—C4E119.8 (7)
C4B—C9B—C1B120.9 (6)C8E—C9E—C1E120.0 (6)
C8B—C9B—C1B118.5 (7)C4E—C9E—C1E120.2 (6)
C8B—O3B—H7B109.5C8E—O3E—H7E109.5
C2B—C10B—H8B109.5C2E—C10E—H8E109.5
C2B—C10B—H9B109.5C2E—C10E—H9E109.5
H8B—C10B—H9B109.5H8E—C10E—H9E109.5
C2B—C10B—H10B109.5C2E—C10E—H10E109.5
H8B—C10B—H10B109.5H8E—C10E—H10E109.5
H9B—C10B—H10B109.5H9E—C10E—H10E109.5
O1C—C1C—O2C117.6 (7)O1F—C1F—O2F117.8 (7)
O1C—C1C—C9C124.3 (7)O1F—C1F—C9F123.1 (7)
O2C—C1C—C9C118.0 (7)O2F—C1F—C9F119.1 (7)
C1C—O2C—C2C119.7 (6)C1F—O2F—C2F120.7 (6)
O2C—C2C—C3C109.8 (6)O2F—C2F—C10F105.9 (6)
O2C—C2C—C10C105.3 (6)O2F—C2F—C3F110.9 (6)
C3C—C2C—C10C112.8 (7)C10F—C2F—C3F113.0 (6)
O2C—C2C—H1C109.6O2F—C2F—H1F109.0
C3C—C2C—H1C109.6C10F—C2F—H1F109.0
C10C—C2C—H1C109.6C3F—C2F—H1F109.0
C4C—C3C—C2C110.7 (7)C4F—C3F—C2F110.3 (6)
C4C—C3C—H2C109.5C4F—C3F—H2F109.6
C2C—C3C—H2C109.5C2F—C3F—H2F109.6
C4C—C3C—H3C109.5C4F—C3F—H3F109.6
C2C—C3C—H3C109.5C2F—C3F—H3F109.6
H2C—C3C—H3C108.1H2F—C3F—H3F108.1
C5C—C4C—C9C119.9 (7)C5F—C4F—C9F120.6 (7)
C5C—C4C—C3C123.4 (7)C5F—C4F—C3F121.7 (7)
C9C—C4C—C3C116.7 (7)C9F—C4F—C3F117.7 (6)
C6C—C5C—C4C120.3 (7)C4F—C5F—C6F118.8 (7)
C6C—C5C—H4C119.8C4F—C5F—H4F120.6
C4C—C5C—H4C119.8C6F—C5F—H4F120.6
C7C—C6C—C5C120.6 (7)C7F—C6F—C5F122.2 (7)
C7C—C6C—H5C119.7C7F—C6F—H5F118.9
C5C—C6C—H5C119.7C5F—C6F—H5F118.9
C8C—C7C—C6C120.7 (8)C6F—C7F—C8F119.1 (7)
C8C—C7C—H6C119.7C6F—C7F—H6F120.4
C6C—C7C—H6C119.7C8F—C7F—H6F120.4
O3C—C8C—C7C119.9 (7)O3F—C8F—C7F119.6 (7)
O3C—C8C—C9C120.7 (7)O3F—C8F—C9F120.2 (8)
C7C—C8C—C9C119.3 (8)C7F—C8F—C9F120.1 (7)
C4C—C9C—C8C119.2 (7)C8F—C9F—C4F119.0 (7)
C4C—C9C—C1C122.1 (7)C8F—C9F—C1F120.5 (7)
C8C—C9C—C1C118.7 (7)C4F—C9F—C1F120.4 (6)
C8C—O3C—H7C109.5C8F—O3F—H7F109.5
C2C—C10C—H8C109.5C2F—C10F—H8F109.5
C2C—C10C—H9C109.5C2F—C10F—H9F109.5
H8C—C10C—H9C109.5H8F—C10F—H9F109.5
C2C—C10C—H10C109.5C2F—C10F—H10F109.5
H8C—C10C—H10C109.5H8F—C10F—H10F109.5
H9C—C10C—H10C109.5H9F—C10F—H10F109.5
O1A—C1A—O2A—C2A165.6 (6)O1D—C1D—O2D—C2D168.3 (6)
C9A—C1A—O2A—C2A16.7 (9)C9D—C1D—O2D—C2D14.6 (10)
C1A—O2A—C2A—C3A47.7 (8)C1D—O2D—C2D—C10D168.8 (6)
C1A—O2A—C2A—C10A170.5 (6)C1D—O2D—C2D—C3D46.2 (8)
O2A—C2A—C3A—C4A52.0 (8)C10D—C2D—C3D—C4D168.9 (7)
C10A—C2A—C3A—C4A169.6 (7)O2D—C2D—C3D—C4D52.8 (8)
C2A—C3A—C4A—C5A152.1 (7)C2D—C3D—C4D—C5D148.6 (8)
C2A—C3A—C4A—C9A30.3 (10)C2D—C3D—C4D—C9D32.3 (10)
C9A—C4A—C5A—C6A0.5 (11)C9D—C4D—C5D—C6D2.4 (12)
C3A—C4A—C5A—C6A178.1 (7)C3D—C4D—C5D—C6D176.7 (8)
C4A—C5A—C6A—C7A1.6 (12)C4D—C5D—C6D—C7D1.2 (13)
C5A—C6A—C7A—C8A2.1 (12)C5D—C6D—C7D—C8D0.3 (13)
C6A—C7A—C8A—O3A177.6 (7)C6D—C7D—C8D—O3D178.9 (8)
C6A—C7A—C8A—C9A1.4 (11)C6D—C7D—C8D—C9D0.5 (12)
C5A—C4A—C9A—C8A0.1 (11)O3D—C8D—C9D—C4D179.9 (7)
C3A—C4A—C9A—C8A177.6 (7)C7D—C8D—C9D—C4D1.7 (12)
C5A—C4A—C9A—C1A177.8 (7)O3D—C8D—C9D—C1D2.3 (12)
C3A—C4A—C9A—C1A0.0 (11)C7D—C8D—C9D—C1D179.4 (7)
O3A—C8A—C9A—C4A176.4 (7)C5D—C4D—C9D—C8D2.7 (12)
C7A—C8A—C9A—C4A0.3 (11)C3D—C4D—C9D—C8D176.4 (7)
O3A—C8A—C9A—C1A1.3 (11)C5D—C4D—C9D—C1D179.6 (7)
C7A—C8A—C9A—C1A177.3 (7)C3D—C4D—C9D—C1D1.2 (11)
O1A—C1A—C9A—C4A169.5 (7)O1D—C1D—C9D—C8D9.7 (12)
O2A—C1A—C9A—C4A8.1 (10)O2D—C1D—C9D—C8D173.5 (7)
O1A—C1A—C9A—C8A8.2 (11)O1D—C1D—C9D—C4D168.0 (7)
O2A—C1A—C9A—C8A174.2 (6)O2D—C1D—C9D—C4D8.9 (11)
O1B—C1B—O2B—C2B169.3 (7)O1E—C1E—O2E—C2E167.6 (7)
C9B—C1B—O2B—C2B12.5 (10)C9E—C1E—O2E—C2E14.4 (10)
C1B—O2B—C2B—C3B44.2 (9)C1E—O2E—C2E—C10E170.8 (6)
C1B—O2B—C2B—C10B167.7 (7)C1E—O2E—C2E—C3E48.1 (8)
O2B—C2B—C3B—C4B53.9 (8)O2E—C2E—C3E—C4E56.5 (8)
C10B—C2B—C3B—C4B171.7 (7)C10E—C2E—C3E—C4E175.1 (7)
C2B—C3B—C4B—C5B146.6 (8)C2E—C3E—C4E—C5E145.0 (7)
C2B—C3B—C4B—C9B35.4 (10)C2E—C3E—C4E—C9E35.1 (9)
C9B—C4B—C5B—C6B1.1 (11)C9E—C4E—C5E—C6E0.3 (12)
C3B—C4B—C5B—C6B176.9 (7)C3E—C4E—C5E—C6E179.8 (8)
C4B—C5B—C6B—C7B0.4 (12)C4E—C5E—C6E—C7E3.0 (13)
C5B—C6B—C7B—C8B0.1 (12)C5E—C6E—C7E—C8E2.2 (12)
C6B—C7B—C8B—O3B178.2 (8)C6E—C7E—C8E—O3E179.8 (7)
C6B—C7B—C8B—C9B0.1 (12)C6E—C7E—C8E—C9E1.3 (12)
C5B—C4B—C9B—C8B1.3 (11)O3E—C8E—C9E—C4E177.2 (7)
C3B—C4B—C9B—C8B176.8 (7)C7E—C8E—C9E—C4E3.9 (12)
C5B—C4B—C9B—C1B178.1 (7)O3E—C8E—C9E—C1E1.8 (11)
C3B—C4B—C9B—C1B3.8 (11)C7E—C8E—C9E—C1E177.1 (7)
O3B—C8B—C9B—C4B177.4 (7)C5E—C4E—C9E—C8E3.0 (11)
C7B—C8B—C9B—C4B0.8 (11)C3E—C4E—C9E—C8E176.8 (7)
O3B—C8B—C9B—C1B3.2 (12)C5E—C4E—C9E—C1E178.0 (7)
C7B—C8B—C9B—C1B178.5 (7)C3E—C4E—C9E—C1E2.2 (11)
O1B—C1B—C9B—C4B169.0 (8)O1E—C1E—C9E—C8E11.1 (12)
O2B—C1B—C9B—C4B9.0 (11)O2E—C1E—C9E—C8E170.9 (7)
O1B—C1B—C9B—C8B11.6 (12)O1E—C1E—C9E—C4E167.9 (7)
O2B—C1B—C9B—C8B170.4 (7)O2E—C1E—C9E—C4E10.1 (11)
O1C—C1C—O2C—C2C167.6 (7)O1F—C1F—O2F—C2F168.8 (7)
C9C—C1C—O2C—C2C12.7 (10)C9F—C1F—O2F—C2F12.9 (10)
C1C—O2C—C2C—C3C45.6 (9)C1F—O2F—C2F—C10F166.9 (7)
C1C—O2C—C2C—C10C167.3 (6)C1F—O2F—C2F—C3F43.9 (9)
O2C—C2C—C3C—C4C54.1 (8)O2F—C2F—C3F—C4F51.6 (8)
C10C—C2C—C3C—C4C171.2 (7)C10F—C2F—C3F—C4F170.4 (7)
C2C—C3C—C4C—C5C148.3 (8)C2F—C3F—C4F—C5F149.4 (7)
C2C—C3C—C4C—C9C33.4 (10)C2F—C3F—C4F—C9F32.9 (9)
C9C—C4C—C5C—C6C1.6 (12)C9F—C4F—C5F—C6F1.2 (12)
C3C—C4C—C5C—C6C176.7 (8)C3F—C4F—C5F—C6F178.9 (8)
C4C—C5C—C6C—C7C0.2 (12)C4F—C5F—C6F—C7F1.1 (13)
C5C—C6C—C7C—C8C0.1 (13)C5F—C6F—C7F—C8F0.0 (12)
C6C—C7C—C8C—O3C178.8 (7)C6F—C7F—C8F—O3F177.4 (7)
C6C—C7C—C8C—C9C0.9 (12)C6F—C7F—C8F—C9F0.8 (11)
C5C—C4C—C9C—C8C2.6 (11)O3F—C8F—C9F—C4F177.5 (7)
C3C—C4C—C9C—C8C175.8 (7)C7F—C8F—C9F—C4F0.7 (11)
C5C—C4C—C9C—C1C178.9 (7)O3F—C8F—C9F—C1F3.5 (11)
C3C—C4C—C9C—C1C0.6 (11)C7F—C8F—C9F—C1F178.3 (7)
O3C—C8C—C9C—C4C177.4 (7)C5F—C4F—C9F—C8F0.4 (11)
C7C—C8C—C9C—C4C2.3 (11)C3F—C4F—C9F—C8F178.2 (7)
O3C—C8C—C9C—C1C1.0 (11)C5F—C4F—C9F—C1F179.3 (7)
C7C—C8C—C9C—C1C178.7 (7)C3F—C4F—C9F—C1F2.9 (10)
O1C—C1C—C9C—C4C168.1 (8)O1F—C1F—C9F—C8F11.9 (12)
O2C—C1C—C9C—C4C11.5 (11)O2F—C1F—C9F—C8F169.9 (7)
O1C—C1C—C9C—C8C8.2 (11)O1F—C1F—C9F—C4F169.1 (8)
O2C—C1C—C9C—C8C172.2 (7)O2F—C1F—C9F—C4F9.1 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3A—H7A···O1A0.841.852.583 (8)146
O3B—H7B···O1B0.841.852.574 (8)144
O3C—H7C···O1C0.841.822.564 (8)147
O3D—H7D···O1D0.841.882.612 (8)145
O3E—H7E···O1E0.841.832.564 (8)145
O3F—H7F···O1F0.841.852.579 (8)145
C2B—H1B···O3Ci1.002.593.450 (11)144
C2F—H1F···O1Dii1.002.603.474 (11)147
C3C—H2C···O2Aii0.992.603.362 (10)134
C3D—H3D···O2Ciii0.992.593.569 (10)170
C6A—H5A···O1D0.952.513.269 (11)138
C6B—H5B···O2Bi0.952.483.422 (10)173
C6D—H5D···O2Di0.952.473.412 (10)170
C6E—H5E···O1Biv0.952.573.328 (10)137
C10D—H9D···O1Aiv0.982.493.402 (10)156
C10B—H9B···O1E0.982.443.371 (10)159
C10F—H9F···O1Civ0.982.483.306 (11)142
Symmetry codes: (i) x1, y, z; (ii) x, y1, z; (iii) x, y+1, z1; (iv) x, y, z1.
R.m.s. deviation (Å) of the plane of atoms C1/C3–C9/O3 and deviation (Å) of the atom from the plane top
Moleculer.m.s.O1O2C2C10
A0.0209-0.175 (8)0.126 (8)0.655 (10)0.444 (12)
B0.02880.141 (10)-0.254 (9)-0.714 (11)-0.541 (13)
C0.0236-0.172 (9)0.213 (9)0.707 (10)0.504 (13)
D0.01860.195 (9)-0.172 (9)-0.688 (10)-0.478 (13)
E0.0322-0.133 (9)0.275 (9)0.774 (10)0.100 (12)
F0.02300.153 (9)-0.243 (8)-0.710 (10)-0.516 (13)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds