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The structure of bi­cyclo­[3.3.0]octane-endo-3,endo-7-diol and bi­cyclo­[3.3.0]octane-endo-3,exo-7-diol, C8H14O2 form 2:1 co-crystals in the monoclinic P21/n space group rather than undergoing separation by means of fractional recrystallization or column chromatography.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021001730/zl2800sup1.cif
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021001730/zl2800Isup3.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989021001730/zl2800Isup3.hkl
Contains datablock I

CCDC reference: 2019203

Key indicators

  • Single-crystal synchrotron study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in main residue
  • R factor = 0.049
  • wR factor = 0.127
  • Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT417_ALERT_2_A Short Inter D-H..H-D H1A ..H2C . 1.24 Ang. x,y,1+z = 1_556 Check
Alert level B PLAT411_ALERT_2_B Short Inter H...H Contact H3A ..H5C . 1.95 Ang. x,y,z = 1_555 Check PLAT411_ALERT_2_B Short Inter H...H Contact H3A ..H1CA . 1.94 Ang. 1-x,1-y,1-z = 3_666 Check
Alert level C PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 8.14 Note PLAT213_ALERT_2_C Atom C3B has ADP max/min Ratio ..... 3.1 prolat PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.3 Note PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.2 Note PLAT411_ALERT_2_C Short Inter H...H Contact H2AB ..H7C . 2.04 Ang. 1-x,1-y,1-z = 3_666 Check PLAT411_ALERT_2_C Short Inter H...H Contact H8AA ..H6CB . 2.06 Ang. -1+x,y,z = 1_455 Check PLAT415_ALERT_2_C Short Inter D-H..H-X H2AA ..H2C . 2.03 Ang. x,y,1+z = 1_556 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 60 Report
Alert level G ABSMU01_ALERT_1_G Calculation of _exptl_absorpt_correction_mu not performed for this radiation type. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 30 Note PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 20 Report PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 6 Report PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 1 Report PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records 2 Report PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records 1 Report PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 2 ) 100% Note PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 3 ) 100% Note PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd 2 ) 11.11 Check PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd 3 ) 0.89 Check PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 27 Note PLAT789_ALERT_4_G Atoms with Negative _atom_site_disorder_group # 48 Check PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms .... ! Info PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 399 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 3 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 3 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 3 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 13 Info
1 ALERT level A = Most likely a serious problem - resolve or explain 2 ALERT level B = A potentially serious problem, consider carefully 8 ALERT level C = Check. Ensure it is not caused by an omission or oversight 20 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 13 ALERT type 2 Indicator that the structure model may be wrong or deficient 7 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check

Computing details top

Data collection: XDS (Kabsch, 2010); cell refinement: XDS (Kabsch, 2010); data reduction: XDS (Kabsch, 2010); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bicyclo[3.3.0]octane-endo-3,endo-7-diol–bicyclo[3.3.0]octane-endo-3,exo-7-diol (2/1) top
Crystal data top
0.66C8H14O2·0.33C8H14O2F(000) = 468
Mr = 142.19Dx = 1.226 Mg m3
Monoclinic, P21/nSynchrotron radiation, λ = 0.71073 Å
a = 6.2758 (3) ÅCell parameters from 1189 reflections
b = 23.6912 (10) Åθ = 1–22°
c = 7.776 (4) ŵ = 0.09 mm1
β = 91.21 (2)°T = 100 K
V = 1155.9 (6) Å3Plate, colourless
Z = 60.02 × 0.02 × 0.01 mm
Data collection top
Area detector at Australian Synchrotron
diffractometer
Rint = 0.066
phi scanθmax = 26.0°, θmin = 3.4°
16006 measured reflectionsh = 77
2215 independent reflectionsk = 2929
2021 reflections with I > 2σ(I)l = 99
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0636P)2 + 0.7974P]
where P = (Fo2 + 2Fc2)/3
2215 reflections(Δ/σ)max = 0.002
272 parametersΔρmax = 0.35 e Å3
399 restraintsΔρmin = 0.23 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1A0.06519 (17)0.34885 (4)1.12882 (14)0.0164 (3)
H1A0.1720450.3605421.1851080.025*
C1A0.0032 (2)0.39024 (6)1.00232 (19)0.0153 (3)
H1AA0.0382810.4264661.0584510.018*
C2A0.1778 (3)0.40019 (6)0.8703 (2)0.0180 (3)
H2AA0.3204850.3998050.9271470.022*
H2AB0.1570430.4370200.8121960.022*
C3A0.1565 (2)0.35136 (6)0.73977 (19)0.0156 (3)
H3A0.1782270.3656900.6204550.019*
C4A0.3023 (2)0.30022 (6)0.7759 (2)0.0159 (3)
H4AA0.4287710.3010680.7019860.019*
H4AB0.3502250.2993380.8979500.019*
C5A0.1606 (2)0.24957 (6)0.73260 (18)0.0139 (3)
H5A0.1456300.2454380.6049340.017*
O2A0.23565 (18)0.19773 (4)0.80652 (14)0.0176 (3)
H2A0.3413840.1862080.7521230.026*
C6A0.0529 (2)0.26608 (6)0.80698 (19)0.0144 (3)
H6AA0.0515140.2612290.9334520.017*
H6AB0.1699630.2431310.7559560.017*
C7A0.0780 (2)0.32858 (6)0.75773 (18)0.0141 (3)
H7A0.1573030.3320250.6453270.017*
C8A0.1819 (2)0.36634 (6)0.89395 (19)0.0153 (3)
H8AA0.2645740.3971630.8382650.018*
H8AB0.2786210.3439600.9662810.018*
O1B0.5861 (19)0.6170 (5)0.6823 (12)0.0159 (13)0.463 (2)
H1B0.4987530.6429170.6590040.024*0.463 (2)
C1B0.4722 (14)0.5665 (4)0.7261 (9)0.0135 (13)0.463 (2)
H1BA0.4066200.5698820.8416880.016*0.463 (2)
C2B0.3060 (7)0.55080 (17)0.5881 (6)0.0158 (8)0.463 (2)
H2BA0.2230170.5843270.5506560.019*0.463 (2)
H2BB0.2067470.5217990.6309770.019*0.463 (2)
C3B0.4388 (6)0.52750 (15)0.4400 (5)0.0160 (8)0.463 (2)
H3B0.4763450.5585190.3588490.019*0.463 (2)
C4B0.3360 (11)0.4772 (3)0.3397 (8)0.0190 (15)0.463 (2)
H4BA0.2207220.4597030.4064270.023*0.463 (2)
H4BB0.2767870.4897210.2270310.023*0.463 (2)
C5B0.5197 (18)0.4358 (4)0.3161 (10)0.0224 (17)0.463 (2)
H5B0.6099580.4487210.2192220.027*0.463 (2)
O2B0.4395 (19)0.3804 (5)0.2803 (13)0.0159 (13)0.463 (2)
H2B0.5405410.3572040.2831880.024*0.463 (2)
C6B0.6454 (9)0.4400 (3)0.4836 (9)0.0144 (10)0.463 (2)
H6BA0.7924940.4259190.4694320.017*0.463 (2)
H6BB0.5764850.4176810.5745840.017*0.463 (2)
C7B0.6468 (6)0.50277 (15)0.5295 (5)0.0150 (7)0.463 (2)
H7B0.7758560.5213420.4818460.018*0.463 (2)
C8B0.6282 (9)0.5170 (2)0.7203 (7)0.0143 (11)0.463 (2)
H8BA0.7686450.5277980.7704670.017*0.463 (2)
H8BB0.5728150.4842520.7847670.017*0.463 (2)
O1C0.530 (10)0.605 (2)0.791 (7)0.013 (3)0.037 (2)
H1C0.4381060.6303660.7801660.019*0.037 (2)
C1C0.560 (7)0.5784 (17)0.631 (6)0.016 (2)0.037 (2)
H1CA0.6357420.6055840.5548580.019*0.037 (2)
C2C0.359 (8)0.559 (3)0.536 (11)0.016 (3)0.037 (2)
H2CA0.2836220.5910600.4809860.019*0.037 (2)
H2CB0.2607120.5398250.6155030.019*0.037 (2)
C3C0.438 (7)0.5170 (14)0.399 (6)0.016 (2)0.037 (2)
H3C0.4506470.5362640.2848380.020*0.037 (2)
C4C0.302 (6)0.4632 (16)0.380 (7)0.018 (3)0.037 (2)
H4CA0.2048990.4596240.4784600.022*0.037 (2)
H4CB0.2151780.4643960.2724470.022*0.037 (2)
C5C0.457 (7)0.4142 (14)0.377 (6)0.018 (3)0.037 (2)
H5C0.3942940.3844750.4525720.022*0.037 (2)
O2C0.478 (11)0.389 (3)0.215 (8)0.016 (4)0.037 (2)
H2C0.3578480.3779210.1781290.024*0.037 (2)
C6C0.657 (9)0.4329 (17)0.468 (10)0.017 (3)0.037 (2)
H6CA0.7827470.4174840.4083040.020*0.037 (2)
H6CB0.6605530.4187320.5875010.020*0.037 (2)
C7C0.666 (6)0.4971 (16)0.467 (6)0.016 (3)0.037 (2)
H7C0.7789800.5105400.3885750.019*0.037 (2)
C8C0.694 (11)0.525 (2)0.646 (7)0.014 (3)0.037 (2)
H8CA0.6414160.5001030.7375440.017*0.037 (2)
H8CB0.8454990.5342560.6700600.017*0.037 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0158 (6)0.0160 (5)0.0173 (6)0.0030 (4)0.0062 (4)0.0011 (4)
C1A0.0169 (8)0.0098 (7)0.0189 (7)0.0002 (5)0.0027 (6)0.0011 (5)
C2A0.0200 (8)0.0097 (7)0.0242 (8)0.0038 (6)0.0005 (6)0.0022 (6)
C3A0.0170 (8)0.0143 (7)0.0156 (7)0.0034 (6)0.0009 (5)0.0026 (6)
C4A0.0124 (7)0.0159 (8)0.0193 (7)0.0024 (5)0.0007 (5)0.0022 (6)
C5A0.0144 (7)0.0132 (7)0.0140 (7)0.0007 (5)0.0003 (5)0.0006 (5)
O2A0.0198 (6)0.0121 (5)0.0211 (6)0.0023 (4)0.0014 (4)0.0002 (4)
C6A0.0127 (7)0.0126 (7)0.0179 (7)0.0032 (5)0.0005 (5)0.0019 (6)
C7A0.0145 (7)0.0146 (7)0.0130 (7)0.0007 (5)0.0039 (5)0.0005 (5)
C8A0.0138 (7)0.0132 (7)0.0186 (7)0.0024 (5)0.0038 (6)0.0005 (6)
O1B0.014 (2)0.0119 (10)0.022 (4)0.0030 (13)0.003 (2)0.0091 (19)
C1B0.012 (2)0.009 (2)0.019 (3)0.0011 (15)0.008 (2)0.004 (2)
C2B0.0156 (19)0.0079 (17)0.024 (2)0.0010 (13)0.0016 (15)0.0003 (15)
C3B0.0218 (16)0.0037 (16)0.0220 (18)0.0016 (15)0.0110 (14)0.0005 (14)
C4B0.023 (3)0.014 (2)0.020 (3)0.005 (2)0.009 (2)0.000 (2)
C5B0.029 (3)0.012 (2)0.026 (3)0.0004 (19)0.005 (3)0.006 (2)
O2B0.014 (2)0.0119 (10)0.022 (4)0.0030 (13)0.003 (2)0.0091 (19)
C6B0.0140 (19)0.009 (2)0.020 (2)0.0024 (14)0.0048 (17)0.0043 (18)
C7B0.0167 (16)0.0077 (15)0.0202 (19)0.0013 (13)0.0088 (14)0.0041 (15)
C8B0.020 (2)0.0069 (18)0.016 (2)0.0010 (14)0.0075 (19)0.0003 (18)
O1C0.011 (6)0.010 (6)0.017 (6)0.003 (6)0.000 (6)0.008 (6)
C1C0.016 (4)0.011 (4)0.020 (4)0.001 (4)0.006 (4)0.003 (4)
C2C0.017 (5)0.008 (5)0.022 (5)0.002 (5)0.004 (5)0.001 (5)
C3C0.019 (4)0.008 (4)0.022 (4)0.004 (4)0.006 (4)0.000 (4)
C4C0.021 (5)0.010 (5)0.023 (5)0.002 (5)0.009 (5)0.001 (5)
C5C0.020 (4)0.012 (4)0.023 (5)0.003 (4)0.005 (4)0.005 (4)
O2C0.018 (6)0.010 (6)0.020 (6)0.001 (6)0.001 (6)0.007 (6)
C6C0.020 (5)0.008 (5)0.022 (5)0.004 (5)0.004 (5)0.005 (5)
C7C0.018 (5)0.008 (5)0.021 (5)0.002 (4)0.008 (5)0.003 (5)
C8C0.015 (5)0.008 (5)0.020 (5)0.002 (5)0.008 (5)0.002 (5)
Geometric parameters (Å, º) top
O1A—H1A0.8400C4B—C5B1.527 (11)
O1A—C1A1.4365 (18)C5B—H5B1.0000
C1A—H1AA1.0000C5B—O2B1.431 (12)
C1A—C2A1.535 (2)C5B—C6B1.511 (9)
C1A—C8A1.530 (2)O2B—H2B0.8400
C2A—H2AA0.9900C6B—H6BA0.9900
C2A—H2AB0.9900C6B—H6BB0.9900
C2A—C3A1.543 (2)C6B—C7B1.529 (6)
C3A—H3A1.0000C7B—H7B1.0000
C3A—C4A1.540 (2)C7B—C8B1.528 (6)
C3A—C7A1.577 (2)C8B—H8BA0.9900
C4A—H4AA0.9900C8B—H8BB0.9900
C4A—H4AB0.9900O1C—H1C0.8400
C4A—C5A1.527 (2)O1C—C1C1.412 (18)
C5A—H5A1.0000C1C—H1CA1.0000
C5A—O2A1.4316 (18)C1C—C2C1.522 (18)
C5A—C6A1.522 (2)C1C—C8C1.521 (18)
O2A—H2A0.8400C2C—H2CA0.9900
C6A—H6AA0.9900C2C—H2CB0.9900
C6A—H6AB0.9900C2C—C3C1.547 (18)
C6A—C7A1.537 (2)C3C—H3C1.0000
C7A—H7A1.0000C3C—C4C1.540 (18)
C7A—C8A1.542 (2)C3C—C7C1.585 (16)
C8A—H8AA0.9900C4C—H4CA0.9900
C8A—H8AB0.9900C4C—H4CB0.9900
O1B—H1B0.8400C4C—C5C1.516 (17)
O1B—C1B1.438 (12)C5C—H5C1.0000
C1B—H1BA1.0000C5C—O2C1.410 (18)
C1B—C2B1.527 (8)C5C—C6C1.496 (17)
C1B—C8B1.530 (9)O2C—H2C0.8400
C2B—H2BA0.9900C6C—H6CA0.9900
C2B—H2BB0.9900C6C—H6CB0.9900
C2B—C3B1.538 (6)C6C—C7C1.522 (17)
C3B—H3B1.0000C7C—H7C1.0000
C3B—C4B1.557 (7)C7C—C8C1.542 (18)
C3B—C7B1.579 (4)C8C—H8CA0.9900
C4B—H4BA0.9900C8C—H8CB0.9900
C4B—H4BB0.9900
C1A—O1A—H1A109.5C4B—C5B—H5B109.6
O1A—C1A—H1AA110.9O2B—C5B—C4B110.4 (9)
O1A—C1A—C2A112.09 (12)O2B—C5B—H5B109.6
O1A—C1A—C8A108.43 (11)O2B—C5B—C6B113.8 (9)
C2A—C1A—H1AA110.9C6B—C5B—C4B103.7 (5)
C8A—C1A—H1AA110.9C6B—C5B—H5B109.6
C8A—C1A—C2A103.49 (12)C5B—O2B—H2B109.5
C1A—C2A—H2AA110.6C5B—C6B—H6BA110.7
C1A—C2A—H2AB110.6C5B—C6B—H6BB110.7
C1A—C2A—C3A105.75 (12)C5B—C6B—C7B105.4 (5)
H2AA—C2A—H2AB108.7H6BA—C6B—H6BB108.8
C3A—C2A—H2AA110.6C7B—C6B—H6BA110.7
C3A—C2A—H2AB110.6C7B—C6B—H6BB110.7
C2A—C3A—H3A110.1C3B—C7B—H7B110.0
C2A—C3A—C7A105.45 (12)C6B—C7B—C3B104.9 (3)
C4A—C3A—C2A115.28 (12)C6B—C7B—H7B110.0
C4A—C3A—H3A110.1C8B—C7B—C3B105.5 (3)
C4A—C3A—C7A105.45 (11)C8B—C7B—C6B116.1 (4)
C7A—C3A—H3A110.1C8B—C7B—H7B110.0
C3A—C4A—H4AA111.0C1B—C8B—H8BA110.7
C3A—C4A—H4AB111.0C1B—C8B—H8BB110.7
H4AA—C4A—H4AB109.0C7B—C8B—C1B105.0 (4)
C5A—C4A—C3A103.72 (12)C7B—C8B—H8BA110.7
C5A—C4A—H4AA111.0C7B—C8B—H8BB110.7
C5A—C4A—H4AB111.0H8BA—C8B—H8BB108.8
C4A—C5A—H5A109.7C1C—O1C—H1C109.5
O2A—C5A—C4A113.61 (12)O1C—C1C—H1CA108.1
O2A—C5A—H5A109.7O1C—C1C—C2C116 (3)
O2A—C5A—C6A110.66 (12)O1C—C1C—C8C113 (2)
C6A—C5A—C4A103.16 (11)C2C—C1C—H1CA108.1
C6A—C5A—H5A109.7C8C—C1C—H1CA108.1
C5A—O2A—H2A109.5C8C—C1C—C2C104 (2)
C5A—C6A—H6AA111.0C1C—C2C—H2CA110.8
C5A—C6A—H6AB111.0C1C—C2C—H2CB110.8
C5A—C6A—C7A103.84 (12)C1C—C2C—C3C104.6 (18)
H6AA—C6A—H6AB109.0H2CA—C2C—H2CB108.9
C7A—C6A—H6AA111.0C3C—C2C—H2CA110.8
C7A—C6A—H6AB111.0C3C—C2C—H2CB110.8
C3A—C7A—H7A110.1C2C—C3C—H3C110.4
C6A—C7A—C3A105.14 (11)C2C—C3C—C7C105.0 (16)
C6A—C7A—H7A110.1C4C—C3C—C2C114 (3)
C6A—C7A—C8A115.49 (12)C4C—C3C—H3C110.4
C8A—C7A—C3A105.76 (11)C4C—C3C—C7C106.3 (15)
C8A—C7A—H7A110.1C7C—C3C—H3C110.4
C1A—C8A—C7A105.40 (12)C3C—C4C—H4CA110.5
C1A—C8A—H8AA110.7C3C—C4C—H4CB110.5
C1A—C8A—H8AB110.7H4CA—C4C—H4CB108.7
C7A—C8A—H8AA110.7C5C—C4C—C3C106.2 (16)
C7A—C8A—H8AB110.7C5C—C4C—H4CA110.5
H8AA—C8A—H8AB108.8C5C—C4C—H4CB110.5
C1B—O1B—H1B109.5C4C—C5C—H5C105.7
O1B—C1B—H1BA111.3O2C—C5C—C4C114 (2)
O1B—C1B—C2B111.9 (8)O2C—C5C—H5C105.7
O1B—C1B—C8B108.1 (8)O2C—C5C—C6C117 (3)
C2B—C1B—H1BA111.3C6C—C5C—C4C107.4 (17)
C2B—C1B—C8B102.7 (5)C6C—C5C—H5C105.7
C8B—C1B—H1BA111.3C5C—O2C—H2C109.5
C1B—C2B—H2BA111.0C5C—C6C—H6CA109.9
C1B—C2B—H2BB111.0C5C—C6C—H6CB109.9
C1B—C2B—C3B103.9 (4)C5C—C6C—C7C108.9 (17)
H2BA—C2B—H2BB109.0H6CA—C6C—H6CB108.3
C3B—C2B—H2BA111.0C7C—C6C—H6CA109.9
C3B—C2B—H2BB111.0C7C—C6C—H6CB109.9
C2B—C3B—H3B110.3C3C—C7C—H7C110.1
C2B—C3B—C4B115.1 (4)C6C—C7C—C3C105.5 (15)
C2B—C3B—C7B105.0 (3)C6C—C7C—H7C110.1
C4B—C3B—H3B110.3C6C—C7C—C8C116 (3)
C4B—C3B—C7B105.5 (3)C8C—C7C—C3C105.1 (16)
C7B—C3B—H3B110.3C8C—C7C—H7C110.1
C3B—C4B—H4BA110.9C1C—C8C—C7C103.6 (18)
C3B—C4B—H4BB110.9C1C—C8C—H8CA111.0
H4BA—C4B—H4BB108.9C1C—C8C—H8CB111.0
C5B—C4B—C3B104.2 (6)C7C—C8C—H8CA111.0
C5B—C4B—H4BA110.9C7C—C8C—H8CB111.0
C5B—C4B—H4BB110.9H8CA—C8C—H8CB109.0
O1A—C1A—C2A—C3A80.65 (15)C3B—C7B—C8B—C1B21.7 (5)
O1A—C1A—C8A—C7A82.34 (14)C4B—C3B—C7B—C6B2.7 (5)
C1A—C2A—C3A—C4A94.67 (15)C4B—C3B—C7B—C8B125.9 (4)
C1A—C2A—C3A—C7A21.20 (15)C4B—C5B—C6B—C7B40.4 (9)
C2A—C1A—C8A—C7A36.83 (14)C5B—C6B—C7B—C3B26.3 (7)
C2A—C3A—C4A—C5A140.20 (13)C5B—C6B—C7B—C8B142.3 (6)
C2A—C3A—C7A—C6A121.19 (12)O2B—C5B—C6B—C7B160.3 (8)
C2A—C3A—C7A—C8A1.47 (15)C6B—C7B—C8B—C1B137.4 (5)
C3A—C4A—C5A—O2A161.11 (12)C7B—C3B—C4B—C5B21.4 (7)
C3A—C4A—C5A—C6A41.26 (14)C8B—C1B—C2B—C3B41.7 (6)
C3A—C7A—C8A—C1A23.66 (14)O1C—C1C—C2C—C3C163 (4)
C4A—C3A—C7A—C6A1.22 (14)O1C—C1C—C8C—C7C168 (4)
C4A—C3A—C7A—C8A123.88 (12)C1C—C2C—C3C—C4C137 (5)
C4A—C5A—C6A—C7A42.17 (14)C1C—C2C—C3C—C7C21 (5)
C5A—C6A—C7A—C3A26.43 (14)C2C—C1C—C8C—C7C42 (5)
C5A—C6A—C7A—C8A142.58 (12)C2C—C3C—C4C—C5C134 (4)
O2A—C5A—C6A—C7A164.03 (11)C2C—C3C—C7C—C6C127 (5)
C6A—C7A—C8A—C1A92.14 (14)C2C—C3C—C7C—C8C4 (5)
C7A—C3A—C4A—C5A24.33 (14)C3C—C4C—C5C—O2C107 (4)
C8A—C1A—C2A—C3A35.97 (14)C3C—C4C—C5C—C6C24 (5)
O1B—C1B—C2B—C3B74.0 (7)C3C—C7C—C8C—C1C28 (5)
O1B—C1B—C8B—C7B79.0 (7)C4C—C3C—C7C—C6C6 (5)
C1B—C2B—C3B—C4B143.5 (5)C4C—C3C—C7C—C8C117 (5)
C1B—C2B—C3B—C7B28.0 (5)C4C—C5C—C6C—C7C21 (6)
C2B—C1B—C8B—C7B39.4 (6)C5C—C6C—C7C—C3C9 (6)
C2B—C3B—C4B—C5B136.7 (5)C5C—C6C—C7C—C8C125 (5)
C2B—C3B—C7B—C6B119.3 (4)O2C—C5C—C6C—C7C109 (5)
C2B—C3B—C7B—C8B3.9 (4)C6C—C7C—C8C—C1C144 (4)
C3B—C4B—C5B—O2B160.1 (7)C7C—C3C—C4C—C5C18 (4)
C3B—C4B—C5B—C6B38.0 (9)C8C—C1C—C2C—C3C40 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O1Bi0.841.892.732 (12)177
O1A—H1A···O2Bii0.841.882.710 (12)170
O1A—H1A···O1Ci0.842.052.83 (6)154
O1A—H1A···O2Cii0.842.042.82 (7)155
C2A—H2AA···O1Ci0.992.373.18 (5)139
C2A—H2AA···O2Cii0.992.443.25 (6)139
O2A—H2A···O1Aiii0.841.912.7432 (16)173
O1B—H1B···O2Aiv0.841.982.784 (12)159
O2B—H2B···O2Aiii0.841.792.629 (12)173
O1C—H1C···O2Aiv0.842.042.86 (5)164
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y, z+1; (iii) x+1/2, y+1/2, z1/2; (iv) x+1/2, y+1/2, z+3/2.
 

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