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The host compound 9-(1-naphth­yl)-9H-xanthen-9-ol, forms an inclusion compound with acetone, C23H16O2·C3H6O; two independent mol­ecules of each comprise the asymmetric unit. Despite both host and guest mol­ecules being achiral, the resultant host–guest crystal structure is chiral. The structure is stabilized by O(host)—H...O(guest) hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806002820/tk6300sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806002820/tk6300Isup2.hkl
Contains datablock I

CCDC reference: 298556

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.049
  • wR factor = 0.124
  • Data-to-parameter ratio = 7.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 86 PerFit
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.18 PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ......... 1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C2GA PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 16 PLAT737_ALERT_1_C D...A Calc 2.730(4), Rep 2.7300(10) ...... 4.00 su-Rat O2 -O1G 1.555 1.555 PLAT737_ALERT_1_C D...A Calc 2.859(4), Rep 2.8570(10) ...... 4.00 su-Rat O2A -O1# 1.555 1.555
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 25.30 From the CIF: _reflns_number_total 3789 Count of symmetry unique reflns 3798 Completeness (_total/calc) 99.76% 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 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 1999) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

9-(1-naphthyl)-9H-xanthen-9-ol acetone solvate top
Crystal data top
C23H16O2·C3H6OF(000) = 808
Mr = 382.44Dx = 1.293 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 7121 reflections
a = 11.580 (2) Åθ = 3.5–25.3°
b = 9.7036 (19) ŵ = 0.08 mm1
c = 17.489 (4) ÅT = 113 K
β = 90.70 (3)°Rectangular, colourless
V = 1965.1 (7) Å30.39 × 0.32 × 0.27 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
2768 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 25.3°, θmin = 3.5°
φ scans and ωh = 1313
7121 measured reflectionsk = 1111
3789 independent reflectionsl = 2121
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) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0759P)2]
where P = (Fo2 + 2Fc2)/3
3789 reflections(Δ/σ)max < 0.001
528 parametersΔρmax = 0.26 e Å3
5 restraintsΔρmin = 0.25 e Å3
Special details top

Experimental. none

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
O10.3528 (2)0.5153 (3)0.34089 (16)0.0392 (7)
C10.4411 (3)0.5599 (4)0.2950 (2)0.0273 (9)
O20.5954 (2)0.2745 (3)0.31943 (12)0.0303 (7)
H10.582 (3)0.314 (3)0.3695 (8)0.036*
C20.4537 (3)0.7012 (5)0.2914 (2)0.0336 (10)
H20.40240.75970.31840.040*
C30.5414 (3)0.7569 (5)0.2484 (2)0.0327 (10)
H30.55100.85400.24600.039*
C40.6155 (3)0.6714 (5)0.2084 (2)0.0320 (10)
H40.67620.70920.17890.038*
C50.5996 (3)0.5300 (4)0.2123 (2)0.0291 (10)
H50.64960.47140.18450.035*
C60.5124 (3)0.4712 (4)0.2560 (2)0.0263 (9)
C70.5044 (3)0.3163 (4)0.2664 (2)0.0256 (9)
C80.3893 (3)0.2787 (4)0.30224 (19)0.0259 (9)
C90.3479 (3)0.1432 (4)0.3034 (2)0.0298 (10)
H90.38910.07410.27670.036*
C100.2497 (3)0.1068 (5)0.3418 (2)0.0336 (10)
H100.22380.01390.34170.040*
C110.1888 (4)0.2074 (5)0.3807 (2)0.0338 (11)
H110.12160.18290.40830.041*
C120.2251 (3)0.3426 (5)0.3797 (2)0.0345 (10)
H120.18260.41160.40570.041*
C130.3247 (3)0.3770 (4)0.3402 (2)0.0290 (10)
C140.5263 (3)0.2359 (4)0.1926 (2)0.0251 (9)
C150.6192 (3)0.1472 (4)0.1888 (2)0.0310 (10)
H150.67010.14030.23170.037*
C160.6411 (3)0.0666 (5)0.1236 (2)0.0342 (10)
H160.70570.00640.12330.041*
C170.5700 (3)0.0744 (4)0.0608 (2)0.0320 (10)
H170.58530.01960.01710.038*
C180.4736 (3)0.1638 (4)0.06098 (19)0.0263 (9)
C190.3969 (3)0.1702 (5)0.0024 (2)0.0301 (9)
H190.41260.11630.04640.036*
C200.3019 (3)0.2510 (4)0.0020 (2)0.0315 (9)
H200.25110.25210.04500.038*
C210.2783 (3)0.3336 (4)0.06216 (19)0.0282 (9)
H210.21170.39070.06230.034*
C220.3515 (3)0.3317 (4)0.1246 (2)0.0254 (9)
H220.33480.38880.16710.030*
C230.4510 (3)0.2470 (4)0.12740 (19)0.0237 (8)
O1A1.1616 (2)0.5504 (3)0.17320 (16)0.0377 (7)
C1A1.1808 (3)0.6900 (4)0.1645 (2)0.0281 (9)
O2A0.90054 (19)0.7781 (3)0.16060 (13)0.0323 (7)
H1A0.9412 (19)0.802 (4)0.1142 (8)0.039*
C2A1.2841 (3)0.7240 (4)0.1299 (2)0.0330 (10)
H2A1.33570.65400.11360.040*
C3A1.3106 (3)0.8614 (5)0.1195 (2)0.0328 (10)
H3A1.38050.88620.09520.039*
C4A1.2362 (3)0.9635 (5)0.1442 (2)0.0329 (10)
H4A1.25511.05790.13750.040*
C5A1.1333 (3)0.9260 (4)0.1789 (2)0.0294 (10)
H5A1.08220.99580.19600.035*
C6A1.1040 (3)0.7884 (4)0.18906 (19)0.0253 (9)
C7A0.9853 (3)0.7495 (4)0.21983 (19)0.0252 (9)
C8A0.9799 (3)0.5960 (4)0.2366 (2)0.0247 (9)
C9A0.8857 (3)0.5384 (5)0.2749 (2)0.0313 (10)
H9A0.82720.59730.29400.038*
C10A0.8764 (3)0.3976 (5)0.2853 (2)0.0319 (10)
H10A0.81130.36050.31050.038*
C11A0.9616 (3)0.3112 (5)0.2591 (2)0.0325 (10)
H11A0.95530.21460.26670.039*
C12A1.0552 (4)0.3642 (5)0.2221 (2)0.0331 (10)
H12A1.11400.30450.20410.040*
C13A1.0640 (3)0.5053 (4)0.2110 (2)0.0285 (10)
C14A0.9533 (3)0.8351 (4)0.2903 (2)0.0259 (9)
C15A0.8575 (3)0.9171 (4)0.2884 (2)0.0312 (10)
H15A0.81180.92090.24300.037*
C16A0.8246 (4)0.9966 (5)0.3524 (2)0.0375 (10)
H16A0.75761.05290.34970.045*
C17A0.8885 (3)0.9921 (5)0.4173 (2)0.0348 (10)
H17A0.86581.04570.46000.042*
C18A0.9893 (3)0.9087 (4)0.4231 (2)0.0304 (9)
C19A1.0582 (3)0.9082 (5)0.4902 (2)0.0369 (10)
H19A1.03600.96330.53250.044*
C20A1.1561 (4)0.8302 (5)0.4958 (2)0.0366 (10)
H20A1.20130.83070.54150.044*
C21A1.1894 (3)0.7495 (5)0.4334 (2)0.0319 (9)
H21A1.25780.69560.43690.038*
C22A1.1250 (3)0.7472 (4)0.36744 (19)0.0270 (9)
H22A1.14850.69030.32630.032*
C23A1.0234 (3)0.8285 (4)0.35919 (19)0.0264 (9)
O1G0.5482 (3)0.3612 (4)0.46420 (16)0.0533 (8)
C1G0.6139 (4)0.5917 (6)0.4594 (3)0.0566 (13)
H1G10.67220.61340.49860.085*
H1G20.56720.67380.44850.085*
H1G30.65230.56180.41260.085*
C2G0.5372 (4)0.4781 (5)0.4875 (3)0.0477 (12)
C3G0.4512 (4)0.5110 (6)0.5470 (3)0.0587 (14)
H3G10.41000.42680.56140.088*
H3G20.39590.57880.52690.088*
H3G30.49090.54910.59210.088*
O1GA0.9995 (3)0.8472 (3)0.01662 (14)0.0482 (8)
C1GA1.0779 (5)0.6607 (7)0.0491 (3)0.0752 (16)*
H1G41.14210.61620.02170.113*
H1G51.08970.65290.10430.113*
H1G61.00520.61550.03560.113*
C2GA1.0727 (3)0.8066 (5)0.0276 (2)0.0377 (10)
C3GA1.1580 (4)0.8997 (6)0.0627 (2)0.0493 (12)
H3G41.14080.90890.11750.074*
H3G51.23570.86150.05560.074*
H3G61.15390.99050.03840.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0386 (17)0.0274 (19)0.0520 (17)0.0048 (14)0.0194 (14)0.0032 (13)
C10.028 (2)0.026 (3)0.028 (2)0.0019 (18)0.0041 (18)0.0023 (17)
O20.0292 (14)0.0344 (17)0.0274 (13)0.0001 (13)0.0032 (11)0.0057 (13)
C20.032 (2)0.030 (3)0.038 (2)0.0025 (19)0.0032 (19)0.0034 (19)
C30.038 (2)0.023 (2)0.037 (2)0.007 (2)0.0028 (19)0.0006 (19)
C40.032 (2)0.033 (3)0.031 (2)0.009 (2)0.0027 (18)0.0002 (19)
C50.028 (2)0.030 (3)0.030 (2)0.0023 (19)0.0018 (17)0.0026 (18)
C60.029 (2)0.025 (2)0.0246 (18)0.0016 (18)0.0001 (16)0.0004 (17)
C70.022 (2)0.030 (2)0.0244 (18)0.0023 (17)0.0004 (16)0.0017 (17)
C80.028 (2)0.027 (2)0.0227 (19)0.0012 (19)0.0026 (16)0.0058 (18)
C90.031 (2)0.029 (3)0.029 (2)0.0013 (19)0.0004 (18)0.0002 (18)
C100.036 (2)0.031 (3)0.033 (2)0.007 (2)0.0008 (19)0.0033 (19)
C110.031 (2)0.040 (3)0.030 (2)0.007 (2)0.0016 (18)0.0058 (19)
C120.035 (2)0.035 (3)0.033 (2)0.003 (2)0.0097 (19)0.0007 (19)
C130.034 (2)0.026 (3)0.027 (2)0.0043 (19)0.0041 (17)0.0015 (18)
C140.0214 (19)0.026 (2)0.0279 (19)0.0007 (17)0.0038 (16)0.0005 (17)
C150.029 (2)0.030 (2)0.034 (2)0.0023 (19)0.0024 (18)0.0004 (18)
C160.032 (2)0.032 (3)0.039 (2)0.0072 (19)0.0049 (19)0.0007 (19)
C170.037 (2)0.028 (2)0.032 (2)0.0019 (19)0.0099 (19)0.0015 (18)
C180.029 (2)0.024 (2)0.0262 (19)0.0035 (18)0.0073 (17)0.0031 (17)
C190.037 (2)0.032 (2)0.0213 (19)0.006 (2)0.0070 (17)0.0007 (17)
C200.037 (2)0.031 (2)0.0262 (19)0.008 (2)0.0035 (17)0.0050 (19)
C210.028 (2)0.027 (2)0.0292 (19)0.0018 (17)0.0000 (16)0.0039 (17)
C220.031 (2)0.022 (2)0.0237 (19)0.0035 (17)0.0009 (16)0.0022 (16)
C230.0247 (19)0.022 (2)0.0247 (18)0.0003 (17)0.0056 (15)0.0019 (16)
O1A0.0325 (16)0.0259 (18)0.0552 (17)0.0003 (13)0.0178 (14)0.0013 (14)
C1A0.030 (2)0.024 (3)0.030 (2)0.0000 (18)0.0010 (17)0.0001 (18)
O2A0.0230 (13)0.0424 (19)0.0315 (13)0.0025 (13)0.0013 (11)0.0066 (13)
C2A0.030 (2)0.032 (3)0.037 (2)0.0012 (19)0.0059 (19)0.0004 (19)
C3A0.028 (2)0.035 (3)0.035 (2)0.008 (2)0.0044 (17)0.005 (2)
C4A0.038 (2)0.029 (3)0.032 (2)0.005 (2)0.0021 (18)0.0038 (19)
C5A0.033 (2)0.028 (3)0.028 (2)0.0009 (19)0.0023 (17)0.0009 (18)
C6A0.024 (2)0.030 (3)0.0219 (18)0.0005 (19)0.0008 (15)0.0008 (17)
C7A0.025 (2)0.025 (2)0.0247 (19)0.0036 (18)0.0018 (16)0.0032 (17)
C8A0.022 (2)0.029 (3)0.0223 (18)0.0018 (18)0.0020 (16)0.0041 (17)
C9A0.029 (2)0.035 (3)0.030 (2)0.0000 (19)0.0011 (18)0.0004 (19)
C10A0.030 (2)0.039 (3)0.027 (2)0.009 (2)0.0033 (17)0.0050 (19)
C11A0.037 (2)0.031 (3)0.029 (2)0.007 (2)0.0020 (19)0.0058 (18)
C12A0.035 (2)0.027 (3)0.037 (2)0.0002 (19)0.0014 (19)0.0039 (19)
C13A0.028 (2)0.032 (3)0.0259 (19)0.0075 (19)0.0041 (17)0.0001 (18)
C14A0.025 (2)0.024 (2)0.0286 (19)0.0017 (18)0.0057 (16)0.0054 (16)
C15A0.029 (2)0.032 (3)0.033 (2)0.0011 (19)0.0035 (17)0.0019 (18)
C16A0.040 (2)0.032 (3)0.041 (2)0.011 (2)0.009 (2)0.002 (2)
C17A0.040 (2)0.031 (2)0.033 (2)0.003 (2)0.0120 (19)0.0059 (19)
C18A0.037 (2)0.024 (2)0.030 (2)0.007 (2)0.0067 (18)0.0010 (17)
C19A0.048 (3)0.033 (3)0.029 (2)0.008 (2)0.0074 (19)0.0069 (19)
C20A0.040 (2)0.041 (3)0.029 (2)0.005 (2)0.0025 (18)0.0018 (19)
C21A0.034 (2)0.030 (2)0.031 (2)0.002 (2)0.0002 (18)0.0027 (19)
C22A0.032 (2)0.027 (2)0.0226 (18)0.0038 (19)0.0031 (17)0.0001 (17)
C23A0.030 (2)0.018 (2)0.032 (2)0.0043 (17)0.0090 (17)0.0007 (17)
O1G0.060 (2)0.054 (2)0.0458 (17)0.0043 (17)0.0014 (15)0.0109 (17)
C1G0.063 (3)0.055 (3)0.051 (3)0.012 (3)0.015 (2)0.009 (2)
C2G0.050 (3)0.044 (3)0.049 (3)0.004 (2)0.012 (2)0.008 (2)
C3G0.063 (3)0.055 (3)0.058 (3)0.005 (3)0.004 (2)0.013 (3)
O1GA0.0499 (17)0.058 (2)0.0371 (16)0.0034 (16)0.0065 (14)0.0052 (15)
C2GA0.035 (2)0.045 (3)0.033 (2)0.004 (2)0.0048 (19)0.002 (2)
C3GA0.051 (3)0.059 (3)0.038 (2)0.012 (3)0.002 (2)0.001 (2)
Geometric parameters (Å, º) top
O1—C11.377 (5)C3A—H3A0.9500
O1—C131.381 (5)C4A—C5A1.393 (5)
C1—C61.379 (6)C4A—H4A0.9500
C1—C21.381 (6)C5A—C6A1.389 (6)
O2—C71.453 (4)C5A—H5A0.9500
O2—H10.970 (18)C6A—C7A1.530 (5)
C2—C31.382 (6)C7A—C8A1.519 (6)
C2—H20.9500C7A—C14A1.535 (5)
C3—C41.389 (6)C8A—C13A1.391 (6)
C3—H30.9500C8A—C9A1.403 (5)
C4—C51.386 (6)C9A—C10A1.382 (6)
C4—H40.9500C9A—H9A0.9500
C5—C61.396 (5)C10A—C11A1.377 (6)
C5—H50.9500C10A—H10A0.9500
C6—C71.518 (6)C11A—C12A1.370 (5)
C7—C81.524 (5)C11A—H11A0.9500
C7—C141.532 (5)C12A—C13A1.387 (6)
C8—C131.386 (6)C12A—H12A0.9500
C8—C91.400 (6)C14A—C15A1.364 (5)
C9—C101.374 (5)C14A—C23A1.446 (5)
C9—H90.9500C15A—C16A1.416 (6)
C10—C111.388 (6)C15A—H15A0.9500
C10—H100.9500C16A—C17A1.348 (5)
C11—C121.378 (6)C16A—H16A0.9500
C11—H110.9500C17A—C18A1.423 (6)
C12—C131.393 (5)C17A—H17A0.9500
C12—H120.9500C18A—C19A1.412 (5)
C14—C151.380 (5)C18A—C23A1.421 (5)
C14—C231.431 (5)C19A—C20A1.366 (6)
C15—C161.409 (6)C19A—H19A0.9500
C15—H150.9500C20A—C21A1.401 (6)
C16—C171.366 (5)C20A—H20A0.9500
C16—H160.9500C21A—C22A1.366 (5)
C17—C181.414 (5)C21A—H21A0.9500
C17—H170.9500C22A—C23A1.423 (5)
C18—C191.413 (5)C22A—H22A0.9500
C18—C231.441 (5)O1G—C2G1.213 (6)
C19—C201.351 (6)C1G—C2G1.502 (7)
C19—H190.9500C1G—H1G10.9800
C20—C211.408 (5)C1G—H1G20.9800
C20—H200.9500C1G—H1G30.9800
C21—C221.374 (5)C2G—C3G1.485 (6)
C21—H210.9500C3G—H3G10.9800
C22—C231.416 (5)C3G—H3G20.9800
C22—H220.9500C3G—H3G30.9800
O1A—C1A1.381 (5)O1GA—C2GA1.221 (5)
O1A—C13A1.387 (5)C1GA—C2GA1.466 (8)
C1A—C6A1.378 (5)C1GA—H1G40.9800
C1A—C2A1.387 (5)C1GA—H1G50.9800
O2A—C7A1.446 (4)C1GA—H1G60.9800
O2A—H1A0.971 (19)C2GA—C3GA1.477 (6)
C2A—C3A1.381 (6)C3GA—H3G40.9800
C2A—H2A0.9500C3GA—H3G50.9800
C3A—C4A1.385 (6)C3GA—H3G60.9800
C1—O1—C13118.5 (3)C6A—C5A—H5A119.4
O1—C1—C6123.1 (4)C4A—C5A—H5A119.4
O1—C1—C2114.7 (4)C1A—C6A—C5A117.9 (3)
C6—C1—C2122.2 (4)C1A—C6A—C7A121.6 (4)
C7—O2—H1110 (2)C5A—C6A—C7A120.3 (4)
C1—C2—C3119.4 (4)O2A—C7A—C8A107.3 (3)
C1—C2—H2120.3O2A—C7A—C6A107.8 (3)
C3—C2—H2120.3C8A—C7A—C6A110.5 (3)
C2—C3—C4120.3 (4)O2A—C7A—C14A107.6 (3)
C2—C3—H3119.9C8A—C7A—C14A111.4 (3)
C4—C3—H3119.9C6A—C7A—C14A112.1 (3)
C5—C4—C3118.9 (4)C13A—C8A—C9A117.0 (4)
C5—C4—H4120.6C13A—C8A—C7A121.8 (3)
C3—C4—H4120.6C9A—C8A—C7A121.1 (3)
C4—C5—C6122.0 (4)C10A—C9A—C8A121.2 (4)
C4—C5—H5119.0C10A—C9A—H9A119.4
C6—C5—H5119.0C8A—C9A—H9A119.4
C1—C6—C5117.2 (4)C11A—C10A—C9A120.1 (4)
C1—C6—C7121.4 (3)C11A—C10A—H10A120.0
C5—C6—C7121.1 (4)C9A—C10A—H10A120.0
O2—C7—C6108.0 (3)C12A—C11A—C10A120.2 (4)
O2—C7—C8107.6 (3)C12A—C11A—H11A119.9
C6—C7—C8110.0 (3)C10A—C11A—H11A119.9
O2—C7—C14105.6 (3)C11A—C12A—C13A119.8 (4)
C6—C7—C14113.0 (3)C11A—C12A—H12A120.1
C8—C7—C14112.3 (3)C13A—C12A—H12A120.1
C13—C8—C9116.9 (3)C12A—C13A—O1A116.1 (4)
C13—C8—C7120.8 (4)C12A—C13A—C8A121.8 (4)
C9—C8—C7122.1 (4)O1A—C13A—C8A122.1 (4)
C10—C9—C8122.3 (4)C15A—C14A—C23A119.6 (3)
C10—C9—H9118.8C15A—C14A—C7A120.1 (3)
C8—C9—H9118.8C23A—C14A—C7A120.4 (3)
C9—C10—C11119.2 (4)C14A—C15A—C16A121.7 (4)
C9—C10—H10120.4C14A—C15A—H15A119.2
C11—C10—H10120.4C16A—C15A—H15A119.2
C12—C11—C10120.4 (4)C17A—C16A—C15A119.9 (4)
C12—C11—H11119.8C17A—C16A—H16A120.1
C10—C11—H11119.8C15A—C16A—H16A120.1
C11—C12—C13119.3 (4)C16A—C17A—C18A121.3 (4)
C11—C12—H12120.3C16A—C17A—H17A119.3
C13—C12—H12120.3C18A—C17A—H17A119.3
O1—C13—C8123.0 (3)C19A—C18A—C23A119.5 (4)
O1—C13—C12115.2 (4)C19A—C18A—C17A121.0 (4)
C8—C13—C12121.8 (4)C23A—C18A—C17A119.4 (3)
C15—C14—C23118.5 (3)C20A—C19A—C18A121.4 (4)
C15—C14—C7119.6 (3)C20A—C19A—H19A119.3
C23—C14—C7121.8 (3)C18A—C19A—H19A119.3
C14—C15—C16122.2 (4)C19A—C20A—C21A119.4 (4)
C14—C15—H15118.9C19A—C20A—H20A120.3
C16—C15—H15118.9C21A—C20A—H20A120.3
C17—C16—C15120.5 (4)C22A—C21A—C20A120.9 (4)
C17—C16—H16119.7C22A—C21A—H21A119.5
C15—C16—H16119.7C20A—C21A—H21A119.5
C16—C17—C18120.0 (3)C21A—C22A—C23A121.3 (4)
C16—C17—H17120.0C21A—C22A—H22A119.4
C18—C17—H17120.0C23A—C22A—H22A119.4
C19—C18—C17121.0 (3)C18A—C23A—C22A117.4 (3)
C19—C18—C23119.2 (3)C18A—C23A—C14A118.2 (3)
C17—C18—C23119.8 (3)C22A—C23A—C14A124.3 (3)
C20—C19—C18121.7 (4)C2G—C1G—H1G1109.5
C20—C19—H19119.1C2G—C1G—H1G2109.5
C18—C19—H19119.1H1G1—C1G—H1G2109.5
C19—C20—C21120.0 (4)C2G—C1G—H1G3109.5
C19—C20—H20120.0H1G1—C1G—H1G3109.5
C21—C20—H20120.0H1G2—C1G—H1G3109.5
C22—C21—C20120.1 (4)O1G—C2G—C3G120.7 (5)
C22—C21—H21120.0O1G—C2G—C1G120.8 (4)
C20—C21—H21120.0C3G—C2G—C1G118.5 (4)
C21—C22—C23122.0 (3)C2G—C3G—H3G1109.5
C21—C22—H22119.0C2G—C3G—H3G2109.5
C23—C22—H22119.0H3G1—C3G—H3G2109.5
C22—C23—C14124.0 (3)C2G—C3G—H3G3109.5
C22—C23—C18116.9 (3)H3G1—C3G—H3G3109.5
C14—C23—C18119.0 (3)H3G2—C3G—H3G3109.5
C1A—O1A—C13A119.7 (3)C2GA—C1GA—H1G4109.5
C6A—C1A—O1A122.7 (3)C2GA—C1GA—H1G5109.5
C6A—C1A—C2A122.3 (4)H1G4—C1GA—H1G5109.5
O1A—C1A—C2A115.0 (4)C2GA—C1GA—H1G6109.5
C7A—O2A—H1A108.2 (14)H1G4—C1GA—H1G6109.5
C3A—C2A—C1A118.8 (4)H1G5—C1GA—H1G6109.5
C3A—C2A—H2A120.6O1GA—C2GA—C1GA120.3 (4)
C1A—C2A—H2A120.6O1GA—C2GA—C3GA122.6 (4)
C2A—C3A—C4A120.6 (4)C1GA—C2GA—C3GA117.1 (4)
C2A—C3A—H3A119.7C2GA—C3GA—H3G4109.5
C4A—C3A—H3A119.7C2GA—C3GA—H3G5109.5
C3A—C4A—C5A119.2 (4)H3G4—C3GA—H3G5109.5
C3A—C4A—H4A120.4C2GA—C3GA—H3G6109.5
C5A—C4A—H4A120.4H3G4—C3GA—H3G6109.5
C6A—C5A—C4A121.2 (4)H3G5—C3GA—H3G6109.5
C13—O1—C1—C68.6 (5)C13A—O1A—C1A—C6A2.8 (5)
C13—O1—C1—C2171.9 (3)C13A—O1A—C1A—C2A176.4 (3)
O1—C1—C2—C3178.5 (3)C6A—C1A—C2A—C3A0.2 (6)
C6—C1—C2—C30.9 (6)O1A—C1A—C2A—C3A179.4 (4)
C1—C2—C3—C40.6 (6)C1A—C2A—C3A—C4A0.9 (6)
C2—C3—C4—C50.3 (6)C2A—C3A—C4A—C5A0.7 (5)
C3—C4—C5—C60.9 (6)C3A—C4A—C5A—C6A0.2 (6)
O1—C1—C6—C5179.0 (3)O1A—C1A—C6A—C5A178.5 (4)
C2—C1—C6—C50.4 (6)C2A—C1A—C6A—C5A0.6 (5)
O1—C1—C6—C75.2 (6)O1A—C1A—C6A—C7A7.0 (5)
C2—C1—C6—C7174.2 (4)C2A—C1A—C6A—C7A173.8 (3)
C4—C5—C6—C10.5 (6)C4A—C5A—C6A—C1A0.8 (6)
C4—C5—C6—C7173.3 (3)C4A—C5A—C6A—C7A173.7 (3)
C1—C6—C7—O299.3 (4)C1A—C6A—C7A—O2A103.1 (4)
C5—C6—C7—O274.3 (4)C5A—C6A—C7A—O2A71.2 (4)
C1—C6—C7—C817.8 (5)C1A—C6A—C7A—C8A13.8 (5)
C5—C6—C7—C8168.6 (3)C5A—C6A—C7A—C8A171.9 (3)
C1—C6—C7—C14144.2 (3)C1A—C6A—C7A—C14A138.7 (3)
C5—C6—C7—C1442.2 (5)C5A—C6A—C7A—C14A47.0 (5)
O2—C7—C8—C1398.6 (4)O2A—C7A—C8A—C13A104.7 (4)
C6—C7—C8—C1318.7 (5)C6A—C7A—C8A—C13A12.5 (5)
C14—C7—C8—C13145.5 (3)C14A—C7A—C8A—C13A137.8 (3)
O2—C7—C8—C976.7 (4)O2A—C7A—C8A—C9A71.4 (4)
C6—C7—C8—C9166.0 (3)C6A—C7A—C8A—C9A171.3 (3)
C14—C7—C8—C939.2 (5)C14A—C7A—C8A—C9A46.1 (5)
C13—C8—C9—C101.7 (5)C13A—C8A—C9A—C10A1.1 (5)
C7—C8—C9—C10173.8 (3)C7A—C8A—C9A—C10A175.2 (3)
C8—C9—C10—C110.2 (6)C8A—C9A—C10A—C11A1.2 (6)
C9—C10—C11—C121.2 (6)C9A—C10A—C11A—C12A0.6 (5)
C10—C11—C12—C131.0 (6)C10A—C11A—C12A—C13A0.1 (6)
C1—O1—C13—C87.5 (5)C11A—C12A—C13A—O1A179.8 (3)
C1—O1—C13—C12171.6 (3)C11A—C12A—C13A—C8A0.1 (6)
C9—C8—C13—O1177.2 (3)C1A—O1A—C13A—C12A175.6 (3)
C7—C8—C13—O17.3 (5)C1A—O1A—C13A—C8A4.1 (5)
C9—C8—C13—C121.9 (5)C9A—C8A—C13A—C12A0.4 (5)
C7—C8—C13—C12173.7 (3)C7A—C8A—C13A—C12A175.8 (4)
C11—C12—C13—O1178.6 (3)C9A—C8A—C13A—O1A179.2 (3)
C11—C12—C13—C80.6 (6)C7A—C8A—C13A—O1A4.5 (5)
O2—C7—C14—C150.3 (5)O2A—C7A—C14A—C15A0.9 (5)
C6—C7—C14—C15117.5 (4)C8A—C7A—C14A—C15A116.4 (4)
C8—C7—C14—C15117.3 (4)C6A—C7A—C14A—C15A119.3 (4)
O2—C7—C14—C23177.9 (3)O2A—C7A—C14A—C23A179.7 (3)
C6—C7—C14—C2364.3 (5)C8A—C7A—C14A—C23A63.0 (4)
C8—C7—C14—C2360.9 (5)C6A—C7A—C14A—C23A61.3 (5)
C23—C14—C15—C160.8 (6)C23A—C14A—C15A—C16A0.0 (6)
C7—C14—C15—C16177.4 (4)C7A—C14A—C15A—C16A179.4 (4)
C14—C15—C16—C170.3 (6)C14A—C15A—C16A—C17A0.0 (6)
C15—C16—C17—C180.0 (6)C15A—C16A—C17A—C18A0.0 (6)
C16—C17—C18—C19178.0 (4)C16A—C17A—C18A—C19A177.7 (4)
C16—C17—C18—C230.3 (5)C16A—C17A—C18A—C23A0.0 (6)
C17—C18—C19—C20177.3 (4)C23A—C18A—C19A—C20A1.2 (6)
C23—C18—C19—C200.9 (6)C17A—C18A—C19A—C20A178.9 (4)
C18—C19—C20—C211.1 (6)C18A—C19A—C20A—C21A0.4 (6)
C19—C20—C21—C220.3 (6)C19A—C20A—C21A—C22A0.4 (6)
C20—C21—C22—C230.8 (6)C20A—C21A—C22A—C23A1.3 (6)
C21—C22—C23—C14176.5 (4)C19A—C18A—C23A—C22A2.0 (5)
C21—C22—C23—C181.0 (5)C17A—C18A—C23A—C22A179.7 (4)
C15—C14—C23—C22178.5 (4)C19A—C18A—C23A—C14A177.8 (3)
C7—C14—C23—C220.3 (6)C17A—C18A—C23A—C14A0.0 (5)
C15—C14—C23—C181.0 (5)C21A—C22A—C23A—C18A2.0 (5)
C7—C14—C23—C18177.1 (3)C21A—C22A—C23A—C14A177.7 (4)
C19—C18—C23—C220.1 (5)C15A—C14A—C23A—C18A0.0 (5)
C17—C18—C23—C22178.4 (3)C7A—C14A—C23A—C18A179.4 (3)
C19—C18—C23—C14177.5 (3)C15A—C14A—C23A—C22A179.7 (4)
C17—C18—C23—C140.8 (5)C7A—C14A—C23A—C22A0.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···O1G0.97 (2)1.77 (2)2.730 (1)172 (2)
O2A—H1A···O1GA0.97 (2)1.90 (2)2.857 (1)171 (2)
 

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