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The title compound was synthesized by treating (1S,3R,8S,9R,10S)-2,2-di­chloro-3,7,7,10-tetra­methyl-9,10-ep­oxy­tri­cyclo­[6.4.0.01,3]dodecane with a concentrated solution of hydro­bromic acid. It is built up from three fused rings: a cyclo­heptane ring, a cyclo­hexyl ring bearing alkene and hy­droxy substituents, and a cyclo­propane ring bearing two chlorine atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016011166/pk2583sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989016011166/pk2583Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989016011166/pk2583Isup3.cml
Supplementary material

CCDC reference: 1491732

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.047
  • wR factor = 0.121
  • Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT213_ALERT_2_C Atom C5C has ADP max/min Ratio ..... 3.6 prolat PLAT213_ALERT_2_C Atom C16B has ADP max/min Ratio ..... 3.1 prolat PLAT220_ALERT_2_C Non-Solvent Resd 1 C Ueq(max)/Ueq(min) Range 4.7 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.0058 Ang. PLAT411_ALERT_2_C Short Inter H...H Contact H6C1 .. H16C .. 2.11 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 Note C16 H24 Cl2 O PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min) 8 Note PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 2 Report PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers .... 1 Check
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 11 Note PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 1 Report PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 1 Report PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records 2 Report PLAT301_ALERT_3_G Main Residue Disorder ............ Percentage = 13 Note PLAT367_ALERT_2_G Long? C(sp?)-C(sp?) Bond C1B - C8B .. 1.53 Ang. PLAT367_ALERT_2_G Long? C(sp?)-C(sp?) Bond C8B - C9B .. 1.55 Ang. PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 16 Note PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note C16 H24 Cl2 O PLAT791_ALERT_4_G The Model has Chirality at C1A (Chiral SPGR) S Verify PLAT791_ALERT_4_G The Model has Chirality at C1B (Chiral SPGR) R Verify PLAT791_ALERT_4_G The Model has Chirality at C3A (Chiral SPGR) R Verify PLAT791_ALERT_4_G The Model has Chirality at C3B (Chiral SPGR) R Verify PLAT791_ALERT_4_G The Model has Chirality at C8A (Chiral SPGR) R Verify PLAT791_ALERT_4_G The Model has Chirality at C9A (Chiral SPGR) S Verify PLAT791_ALERT_4_G The Model has Chirality at C9B (Chiral SPGR) R Verify PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 22 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density 7 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 9 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 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 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 13 ALERT type 4 Improvement, methodology, query or suggestion 1 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.
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: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT2013(Sheldrick, 2015a); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015b); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al., 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015b).

(1S,3R,8R,9R)-2,2-Dichloro-3,7,7-trimethyl-10-methylenetricyclo[6.4.0.01,3]dodecan-9-ol top
Crystal data top
C16H24Cl2ODx = 1.258 Mg m3
Mr = 303.25Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P21212Cell parameters from 5974 reflections
a = 12.3075 (4) Åθ = 3.5–30.6°
b = 13.9332 (7) ŵ = 0.40 mm1
c = 18.6716 (9) ÅT = 180 K
V = 3201.9 (2) Å3Box, colourless
Z = 80.43 × 0.31 × 0.25 mm
F(000) = 1296
Data collection top
Agilent Xcalibur Eos Gemini ultra
diffractometer
7060 independent reflections
Radiation source: Enhance (Mo) X-ray Source6084 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 16.1978 pixels mm-1θmax = 27.1°, θmin = 2.9°
ω scansh = 1515
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1717
Tmin = 0.907, Tmax = 1.000l = 2323
20074 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0522P)2 + 1.8807P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
7060 reflectionsΔρmax = 0.52 e Å3
393 parametersΔρmin = 0.36 e Å3
22 restraintsAbsolute structure: Flack x determined using 2376 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (3)
Special details top

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm, CrysAlisPro (Agilent Technologies, 2014)

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)
Cl1A0.38798 (7)0.19453 (7)0.28372 (5)0.0380 (2)
Cl2A0.15680 (8)0.18866 (9)0.29099 (6)0.0479 (3)
O1A0.3867 (2)0.41044 (17)0.22969 (13)0.0298 (5)
H1A0.38170.46540.24510.045*
C1A0.2588 (3)0.2464 (2)0.16119 (19)0.0257 (7)
C2A0.2689 (3)0.1917 (3)0.2314 (2)0.0316 (8)
C3A0.2659 (3)0.1359 (3)0.1627 (2)0.0362 (9)
C4A0.3710 (4)0.0925 (3)0.1351 (2)0.0461 (11)
H4A10.37380.02520.14850.055*
H4A20.43200.12460.15770.055*
C5A0.3822 (5)0.1010 (3)0.0532 (3)0.0570 (13)
H5A10.45860.09700.04080.068*
H5A20.34590.04670.03120.068*
C6A0.3356 (5)0.1933 (3)0.0211 (2)0.0573 (13)
H6A10.25750.19140.02760.069*
H6A20.34910.19150.03010.069*
C7A0.3755 (4)0.2906 (3)0.0487 (2)0.0372 (9)
C8A0.3567 (3)0.3021 (2)0.13200 (18)0.0256 (7)
H8A0.42080.27420.15510.031*
C9A0.3528 (3)0.4083 (2)0.15632 (18)0.0272 (7)
H9A0.40420.44560.12750.033*
C10A0.2414 (3)0.4547 (3)0.1516 (2)0.0324 (9)
C11A0.1495 (3)0.3959 (3)0.1800 (2)0.0370 (9)
H11A0.08120.42730.16900.044*
H11B0.15560.39110.23170.044*
C12A0.1503 (3)0.2955 (3)0.1473 (2)0.0322 (8)
H12A0.09210.25750.16810.039*
H12B0.13780.29990.09610.039*
C13A0.1662 (4)0.0747 (3)0.1461 (3)0.0516 (12)
H13A0.17200.01430.17060.077*
H13B0.16190.06370.09540.077*
H13C0.10190.10750.16190.077*
C14A0.3170 (5)0.3675 (4)0.0029 (2)0.0568 (13)
H14A0.33220.35660.04680.085*
H14B0.34250.43010.01630.085*
H14C0.24010.36360.01090.085*
C15A0.4969 (4)0.3035 (4)0.0350 (3)0.0612 (14)
H15A0.53650.25380.05920.092*
H15B0.51970.36500.05280.092*
H15C0.51090.30000.01550.092*
C16A0.2287 (4)0.5428 (3)0.1266 (2)0.0436 (10)
H16A0.16010.57090.12620.052*
H16B0.28830.57680.10940.052*
Cl1B0.64962 (7)0.18578 (8)0.20137 (5)0.0415 (2)
Cl2B0.87789 (8)0.21670 (9)0.20248 (6)0.0518 (3)
O1B0.6090 (2)0.39598 (19)0.26805 (12)0.0302 (5)
H1B0.54380.38800.26100.045*
C1B0.7575 (3)0.2429 (3)0.33159 (19)0.0262 (8)
C2B0.7636 (3)0.1965 (3)0.2577 (2)0.0308 (8)
C3B0.7751 (3)0.1342 (3)0.3232 (2)0.0356 (9)
C4B0.6812 (4)0.0682 (3)0.3428 (3)0.0572 (14)
H4B10.69390.00500.32260.069*
H4B20.61440.09320.32250.069*
C5B0.669 (2)0.0598 (13)0.4252 (9)0.075 (10)0.498 (8)
H5B10.64550.00410.43870.090*0.498 (8)
H5B20.73710.07390.44910.090*0.498 (8)
C6B0.5817 (8)0.1352 (7)0.4443 (6)0.055 (3)0.498 (8)
H6B10.52030.12630.41250.067*0.498 (8)
H6B20.55660.12260.49270.067*0.498 (8)
C14B0.517 (2)0.2953 (16)0.4674 (17)0.084 (10)0.498 (8)
H14D0.49800.27210.51410.126*0.498 (8)
H14E0.45740.28510.43510.126*0.498 (8)
H14F0.53310.36260.47000.126*0.498 (8)
C15B0.7119 (9)0.2558 (8)0.4924 (5)0.054 (3)0.498 (8)
H15D0.73430.32180.49120.082*0.498 (8)
H15E0.77180.21550.47890.082*0.498 (8)
H15F0.68870.23950.54000.082*0.498 (8)
C7B0.6177 (18)0.2408 (11)0.4400 (15)0.043 (3)0.498 (8)
C5C0.656 (2)0.0716 (12)0.4234 (7)0.064 (8)0.502 (8)
H5C10.69160.01760.44620.077*0.502 (8)
H5C20.57810.06260.42950.077*0.502 (8)
C6C0.6896 (8)0.1660 (6)0.4647 (5)0.059 (3)0.502 (8)
H6C10.67570.15560.51520.071*0.502 (8)
H6C20.76750.17380.45920.071*0.502 (8)
C14C0.5122 (19)0.2525 (16)0.4543 (15)0.073 (7)0.502 (8)
H14G0.49760.23650.50340.110*0.502 (8)
H14H0.48460.20280.42380.110*0.502 (8)
H14I0.47750.31220.44280.110*0.502 (8)
C15C0.6759 (9)0.3422 (7)0.4933 (4)0.054 (3)0.502 (8)
H15G0.63220.39860.48670.081*0.502 (8)
H15H0.75030.35680.48230.081*0.502 (8)
H15I0.67060.32120.54220.081*0.502 (8)
C7C0.6353 (18)0.2623 (11)0.4434 (14)0.043 (3)0.502 (8)
C8B0.6477 (3)0.2777 (3)0.36065 (19)0.0314 (8)
H8B0.59440.24540.33000.038*
C9B0.6317 (4)0.3854 (3)0.3432 (2)0.0401 (10)
H9B0.57030.41030.37100.048*
C10B0.7308 (5)0.4468 (3)0.3572 (3)0.0603 (15)
C11B0.8344 (4)0.4091 (3)0.3272 (3)0.0531 (13)
H11C0.89430.44940.34260.064*
H11D0.83140.41100.27530.064*
C12B0.8540 (3)0.3069 (3)0.3517 (2)0.0365 (9)
H12C0.86430.30580.40320.044*
H12D0.91960.28230.32940.044*
C13B0.8857 (4)0.0895 (3)0.3402 (3)0.0516 (12)
H13D0.89780.03530.30950.077*
H13E0.88690.06890.38930.077*
H13F0.94190.13620.33260.077*
C16B0.7226 (8)0.5295 (5)0.3905 (4)0.122 (4)
H16C0.78370.56790.39640.147*
H16D0.65580.54950.40830.147*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0268 (4)0.0437 (5)0.0436 (5)0.0046 (4)0.0118 (4)0.0125 (4)
Cl2A0.0306 (5)0.0585 (6)0.0545 (6)0.0073 (5)0.0058 (4)0.0172 (6)
O1A0.0319 (12)0.0283 (12)0.0293 (12)0.0013 (11)0.0054 (11)0.0061 (10)
C1A0.0208 (17)0.0238 (17)0.0326 (18)0.0037 (13)0.0079 (14)0.0010 (14)
C2A0.0213 (15)0.0320 (18)0.041 (2)0.0052 (17)0.0068 (14)0.0065 (17)
C3A0.0295 (19)0.0258 (18)0.053 (2)0.0023 (16)0.0125 (18)0.0034 (18)
C4A0.048 (3)0.0273 (18)0.063 (3)0.0091 (19)0.012 (2)0.0074 (19)
C5A0.072 (3)0.040 (2)0.059 (3)0.016 (2)0.006 (3)0.024 (2)
C6A0.082 (4)0.049 (3)0.041 (2)0.004 (3)0.008 (2)0.020 (2)
C7A0.044 (2)0.038 (2)0.0295 (18)0.0011 (17)0.0010 (17)0.0053 (15)
C8A0.0252 (16)0.0249 (16)0.0265 (16)0.0032 (14)0.0008 (13)0.0016 (14)
C9A0.0296 (17)0.0242 (16)0.0278 (17)0.0053 (14)0.0014 (14)0.0016 (14)
C10A0.041 (2)0.0277 (18)0.0285 (19)0.0029 (16)0.0082 (16)0.0058 (15)
C11A0.0293 (18)0.037 (2)0.045 (2)0.0118 (17)0.0042 (16)0.0015 (17)
C12A0.0247 (17)0.0319 (19)0.040 (2)0.0009 (15)0.0075 (15)0.0050 (15)
C13A0.051 (3)0.030 (2)0.074 (3)0.016 (2)0.022 (2)0.001 (2)
C14A0.079 (4)0.060 (3)0.031 (2)0.013 (3)0.004 (2)0.003 (2)
C15A0.058 (3)0.082 (4)0.044 (3)0.000 (3)0.023 (2)0.007 (3)
C16A0.055 (3)0.032 (2)0.044 (2)0.007 (2)0.011 (2)0.0018 (18)
Cl1B0.0315 (4)0.0501 (5)0.0429 (5)0.0046 (4)0.0115 (4)0.0152 (5)
Cl2B0.0275 (5)0.0792 (8)0.0487 (6)0.0090 (5)0.0076 (4)0.0049 (5)
O1B0.0291 (12)0.0364 (13)0.0251 (12)0.0029 (12)0.0062 (10)0.0055 (10)
C1B0.0196 (17)0.0272 (18)0.0319 (18)0.0015 (13)0.0059 (14)0.0033 (15)
C2B0.0160 (15)0.0367 (19)0.040 (2)0.0046 (16)0.0020 (13)0.0041 (17)
C3B0.0270 (18)0.0262 (18)0.054 (2)0.0038 (16)0.0087 (18)0.0028 (17)
C4B0.045 (3)0.039 (2)0.087 (4)0.012 (2)0.016 (3)0.018 (2)
C5B0.055 (13)0.045 (9)0.12 (2)0.006 (8)0.003 (12)0.050 (10)
C6B0.038 (5)0.070 (7)0.059 (6)0.002 (5)0.003 (4)0.039 (5)
C14B0.079 (13)0.114 (18)0.058 (13)0.050 (14)0.046 (10)0.044 (14)
C15B0.076 (7)0.058 (7)0.029 (4)0.013 (5)0.000 (4)0.018 (4)
C7B0.041 (6)0.057 (6)0.030 (3)0.007 (5)0.002 (4)0.016 (5)
C5C0.038 (8)0.078 (14)0.077 (13)0.013 (9)0.027 (8)0.061 (10)
C6C0.054 (6)0.073 (8)0.049 (6)0.002 (5)0.010 (4)0.041 (5)
C14C0.049 (8)0.12 (2)0.047 (11)0.022 (11)0.012 (7)0.052 (13)
C15C0.068 (7)0.073 (7)0.022 (4)0.002 (5)0.003 (4)0.005 (4)
C7C0.041 (6)0.057 (6)0.030 (3)0.007 (5)0.002 (4)0.016 (5)
C8B0.0309 (18)0.039 (2)0.0241 (17)0.0113 (16)0.0011 (15)0.0072 (15)
C9B0.056 (3)0.041 (2)0.0233 (18)0.023 (2)0.0019 (18)0.0003 (15)
C10B0.097 (4)0.033 (2)0.051 (3)0.014 (3)0.043 (3)0.010 (2)
C11B0.066 (3)0.036 (2)0.057 (3)0.019 (2)0.029 (2)0.006 (2)
C12B0.0325 (19)0.0370 (19)0.040 (2)0.0046 (18)0.0146 (16)0.0047 (17)
C13B0.037 (2)0.043 (2)0.075 (3)0.017 (2)0.012 (2)0.004 (2)
C16B0.160 (8)0.072 (4)0.134 (7)0.044 (5)0.092 (6)0.065 (4)
Geometric parameters (Å, º) top
Cl1A—C2A1.762 (3)C2B—C3B1.506 (6)
Cl2A—C2A1.773 (4)C3B—C4B1.521 (6)
O1A—C9A1.432 (4)C3B—C13B1.531 (5)
O1A—H1A0.8200C4B—C5C1.538 (15)
C1A—C2A1.521 (5)C4B—C5B1.550 (16)
C1A—C12A1.523 (5)C4B—H4B10.9700
C1A—C8A1.533 (5)C4B—H4B20.9700
C1A—C3A1.542 (5)C5B—C6B1.54 (2)
C2A—C3A1.500 (6)C5B—H5B10.9700
C3A—C4A1.519 (6)C5B—H5B20.9700
C3A—C13A1.527 (6)C6B—C7B1.539 (16)
C4A—C5A1.541 (7)C6B—H6B10.9700
C4A—H4A10.9700C6B—H6B20.9700
C4A—H4A20.9700C14B—C7B1.540 (16)
C5A—C6A1.530 (7)C14B—H14D0.9600
C5A—H5A10.9700C14B—H14E0.9600
C5A—H5A20.9700C14B—H14F0.9600
C6A—C7A1.531 (6)C15B—C7B1.532 (17)
C6A—H6A10.9700C15B—H15D0.9600
C6A—H6A20.9700C15B—H15E0.9600
C7A—C15A1.527 (6)C15B—H15F0.9600
C7A—C14A1.548 (6)C7B—C8B1.61 (3)
C7A—C8A1.582 (5)C5C—C6C1.581 (13)
C8A—C9A1.548 (5)C5C—H5C10.9700
C8A—H8A0.9800C5C—H5C20.9700
C9A—C10A1.518 (5)C6C—C7C1.550 (16)
C9A—H9A0.9800C6C—H6C10.9700
C10A—C16A1.323 (5)C6C—H6C20.9700
C10A—C11A1.494 (6)C14C—C7C1.535 (17)
C11A—C12A1.527 (5)C14C—H14G0.9600
C11A—H11A0.9700C14C—H14H0.9600
C11A—H11B0.9700C14C—H14I0.9600
C12A—H12A0.9700C15C—C7C1.537 (16)
C12A—H12B0.9700C15C—H15G0.9600
C13A—H13A0.9600C15C—H15H0.9600
C13A—H13B0.9600C15C—H15I0.9600
C13A—H13C0.9600C7C—C8B1.57 (3)
C14A—H14A0.9600C8B—C9B1.548 (5)
C14A—H14B0.9600C8B—H8B0.9800
C14A—H14C0.9600C9B—C10B1.512 (7)
C15A—H15A0.9600C9B—H9B0.9800
C15A—H15B0.9600C10B—C16B1.313 (7)
C15A—H15C0.9600C10B—C11B1.489 (8)
C16A—H16A0.9300C11B—C12B1.515 (6)
C16A—H16B0.9300C11B—H11C0.9700
Cl1B—C2B1.760 (4)C11B—H11D0.9700
Cl2B—C2B1.767 (4)C12B—H12C0.9700
O1B—C9B1.439 (4)C12B—H12D0.9700
O1B—H1B0.8200C13B—H13D0.9600
C1B—C2B1.524 (5)C13B—H13E0.9600
C1B—C12B1.532 (5)C13B—H13F0.9600
C1B—C8B1.534 (5)C16B—H16C0.9300
C1B—C3B1.538 (5)C16B—H16D0.9300
C9A—O1A—H1A109.5C4B—C3B—C1B117.6 (4)
C2A—C1A—C12A116.3 (3)C13B—C3B—C1B120.3 (4)
C2A—C1A—C8A119.8 (3)C3B—C4B—C5C111.9 (7)
C12A—C1A—C8A113.7 (3)C3B—C4B—C5B111.0 (9)
C2A—C1A—C3A58.6 (3)C3B—C4B—H4B1109.4
C12A—C1A—C3A120.0 (3)C5B—C4B—H4B1109.4
C8A—C1A—C3A117.9 (3)C3B—C4B—H4B2109.4
C3A—C2A—C1A61.4 (2)C5B—C4B—H4B2109.4
C3A—C2A—Cl1A120.4 (3)H4B1—C4B—H4B2108.0
C1A—C2A—Cl1A122.3 (3)C6B—C5B—C4B104.2 (14)
C3A—C2A—Cl2A120.4 (3)C6B—C5B—H5B1110.9
C1A—C2A—Cl2A119.3 (3)C4B—C5B—H5B1110.9
Cl1A—C2A—Cl2A107.4 (2)C6B—C5B—H5B2110.9
C2A—C3A—C4A118.4 (3)C4B—C5B—H5B2110.9
C2A—C3A—C13A118.9 (4)H5B1—C5B—H5B2108.9
C4A—C3A—C13A113.1 (4)C7B—C6B—C5B116.0 (13)
C2A—C3A—C1A60.0 (2)C7B—C6B—H6B1108.3
C4A—C3A—C1A116.1 (4)C5B—C6B—H6B1108.3
C13A—C3A—C1A120.6 (4)C7B—C6B—H6B2108.3
C3A—C4A—C5A112.4 (4)C5B—C6B—H6B2108.3
C3A—C4A—H4A1109.1H6B1—C6B—H6B2107.4
C5A—C4A—H4A1109.1C7B—C14B—H14D109.5
C3A—C4A—H4A2109.1C7B—C14B—H14E109.5
C5A—C4A—H4A2109.1H14D—C14B—H14E109.5
H4A1—C4A—H4A2107.9C7B—C14B—H14F109.5
C6A—C5A—C4A114.9 (4)H14D—C14B—H14F109.5
C6A—C5A—H5A1108.5H14E—C14B—H14F109.5
C4A—C5A—H5A1108.5C7B—C15B—H15D109.5
C6A—C5A—H5A2108.5C7B—C15B—H15E109.5
C4A—C5A—H5A2108.5H15D—C15B—H15E109.5
H5A1—C5A—H5A2107.5C7B—C15B—H15F109.5
C5A—C6A—C7A119.5 (4)H15D—C15B—H15F109.5
C5A—C6A—H6A1107.4H15E—C15B—H15F109.5
C7A—C6A—H6A1107.4C15B—C7B—C6B108.3 (13)
C5A—C6A—H6A2107.4C15B—C7B—C14B109 (2)
C7A—C6A—H6A2107.4C6B—C7B—C14B102.9 (15)
H6A1—C6A—H6A2107.0C15B—C7B—C8B111.8 (15)
C15A—C7A—C6A111.2 (4)C6B—C7B—C8B114.8 (14)
C15A—C7A—C14A106.3 (4)C14B—C7B—C8B109.4 (16)
C6A—C7A—C14A106.2 (4)C4B—C5C—C6C116.6 (11)
C15A—C7A—C8A107.2 (3)C4B—C5C—H5C1108.1
C6A—C7A—C8A112.0 (3)C6C—C5C—H5C1108.1
C14A—C7A—C8A113.8 (3)C4B—C5C—H5C2108.1
C1A—C8A—C9A110.8 (3)C6C—C5C—H5C2108.1
C1A—C8A—C7A114.4 (3)H5C1—C5C—H5C2107.3
C9A—C8A—C7A113.0 (3)C7C—C6C—C5C118.7 (13)
C1A—C8A—H8A106.0C7C—C6C—H6C1107.6
C9A—C8A—H8A106.0C5C—C6C—H6C1107.6
C7A—C8A—H8A106.0C7C—C6C—H6C2107.6
O1A—C9A—C10A108.1 (3)C5C—C6C—H6C2107.6
O1A—C9A—C8A107.0 (3)H6C1—C6C—H6C2107.1
C10A—C9A—C8A114.7 (3)C7C—C14C—H14G109.5
O1A—C9A—H9A109.0C7C—C14C—H14H109.5
C10A—C9A—H9A109.0H14G—C14C—H14H109.5
C8A—C9A—H9A109.0C7C—C14C—H14I109.5
C16A—C10A—C11A123.0 (4)H14G—C14C—H14I109.5
C16A—C10A—C9A121.5 (4)H14H—C14C—H14I109.5
C11A—C10A—C9A115.4 (3)C7C—C15C—H15G109.5
C10A—C11A—C12A110.8 (3)C7C—C15C—H15H109.5
C10A—C11A—H11A109.5H15G—C15C—H15H109.5
C12A—C11A—H11A109.5C7C—C15C—H15I109.5
C10A—C11A—H11B109.5H15G—C15C—H15I109.5
C12A—C11A—H11B109.5H15H—C15C—H15I109.5
H11A—C11A—H11B108.1C14C—C7C—C15C107.7 (19)
C1A—C12A—C11A110.4 (3)C14C—C7C—C6C108.4 (15)
C1A—C12A—H12A109.6C15C—C7C—C6C109.3 (13)
C11A—C12A—H12A109.6C14C—C7C—C8B103.9 (15)
C1A—C12A—H12B109.6C15C—C7C—C8B117.9 (14)
C11A—C12A—H12B109.6C6C—C7C—C8B109.3 (15)
H12A—C12A—H12B108.1C1B—C8B—C9B110.1 (3)
C3A—C13A—H13A109.5C1B—C8B—C7C113.0 (8)
C3A—C13A—H13B109.5C9B—C8B—C7C109.1 (6)
H13A—C13A—H13B109.5C1B—C8B—C7B115.2 (8)
C3A—C13A—H13C109.5C9B—C8B—C7B118.3 (7)
H13A—C13A—H13C109.5C1B—C8B—H8B103.7
H13B—C13A—H13C109.5C9B—C8B—H8B103.7
C7A—C14A—H14A109.5C7B—C8B—H8B103.7
C7A—C14A—H14B109.5O1B—C9B—C10B105.5 (4)
H14A—C14A—H14B109.5O1B—C9B—C8B109.2 (3)
C7A—C14A—H14C109.5C10B—C9B—C8B114.2 (3)
H14A—C14A—H14C109.5O1B—C9B—H9B109.3
H14B—C14A—H14C109.5C10B—C9B—H9B109.3
C7A—C15A—H15A109.5C8B—C9B—H9B109.3
C7A—C15A—H15B109.5C16B—C10B—C11B123.6 (7)
H15A—C15A—H15B109.5C16B—C10B—C9B121.1 (7)
C7A—C15A—H15C109.5C11B—C10B—C9B115.2 (4)
H15A—C15A—H15C109.5C10B—C11B—C12B110.7 (4)
H15B—C15A—H15C109.5C10B—C11B—H11C109.5
C10A—C16A—H16A120.0C12B—C11B—H11C109.5
C10A—C16A—H16B120.0C10B—C11B—H11D109.5
H16A—C16A—H16B120.0C12B—C11B—H11D109.5
C9B—O1B—H1B109.5H11C—C11B—H11D108.1
C2B—C1B—C12B115.5 (3)C11B—C12B—C1B110.5 (3)
C2B—C1B—C8B119.8 (3)C11B—C12B—H12C109.6
C12B—C1B—C8B114.3 (3)C1B—C12B—H12C109.6
C2B—C1B—C3B58.9 (3)C11B—C12B—H12D109.6
C12B—C1B—C3B119.3 (3)C1B—C12B—H12D109.6
C8B—C1B—C3B118.2 (3)H12C—C12B—H12D108.1
C3B—C2B—C1B61.0 (2)C3B—C13B—H13D109.5
C3B—C2B—Cl1B120.7 (3)C3B—C13B—H13E109.5
C1B—C2B—Cl1B122.5 (3)H13D—C13B—H13E109.5
C3B—C2B—Cl2B119.4 (3)C3B—C13B—H13F109.5
C1B—C2B—Cl2B120.0 (3)H13D—C13B—H13F109.5
Cl1B—C2B—Cl2B107.4 (2)H13E—C13B—H13F109.5
C2B—C3B—C4B118.2 (4)C10B—C16B—H16C120.0
C2B—C3B—C13B119.2 (4)C10B—C16B—H16D120.0
C4B—C3B—C13B112.3 (3)H16C—C16B—H16D120.0
C2B—C3B—C1B60.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O1Bi0.821.982.791 (4)169
C8A—H8A···Cl1A0.982.683.228 (4)116
O1B—H1B···O1A0.822.042.835 (4)162
C8B—H8B···Cl1A0.982.783.691 (4)156
C8B—H8B···Cl1B0.982.633.238 (4)120
O1A—H1A···O1Bi0.821.982.791 (4)169
C8A—H8A···Cl1A0.982.683.228 (4)116
O1B—H1B···O1A0.822.042.835 (4)162
C8B—H8B···Cl1A0.982.783.691 (4)156
C8B—H8B···Cl1B0.982.633.238 (4)120
Symmetry code: (i) x+1, y1, z.
 

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