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The title compounds, C8H10O2, (I), and C12H14O2, (II), occurred as by-products in the controlled synthesis of a series of bis­(gem-alkynols), prepared as part of an extensive study of synthon formation in simple gem-alkynol derivatives. The two 4-(gem-alkynol)-1-ones crystallize in space group P21/c, (I) with Z′ = 1 and (II) with Z′ = 2. Both structures are dominated by O—H...O=C hydrogen bonds, which form simple chains in the cyclo­hexane derivative, (I), and centrosymmetric dimers, of both symmetry-independent mol­ecules, in the cyclo­hexa-2,5-diene, (II). These strong synthons are further stabilized by C[triple bond]C—H...O=C, Cmethylene—H...O(H) and Cmethyl—H...O(H) interactions. The direct intermolecular interactions between donors and acceptors in the gem-alkynol group, which characterize the bis­(gem-alkynol) analogues of (I) and (II), are not present in the ketone derivatives studied here.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100011355/gd1109sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100011355/gd1109Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100011355/gd1109IIsup3.hkl
Contains datablock II

CCDC references: 153901; 153902

Computing details top

For both compounds, data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

(I) 4-ethynyl-4-hydroxycyclohexan-1-one top
Crystal data top
C8H10O2F(000) = 296
Mr = 138.16Dx = 1.280 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.550 (1) ÅCell parameters from 508 reflections
b = 16.931 (3) Åθ = 6.7–21.2°
c = 6.493 (1) ŵ = 0.09 mm1
β = 95.42 (3)°T = 150 K
V = 716.9 (2) Å3Plate, colourless
Z = 40.40 × 0.10 × 0.05 mm
Data collection top
Bruker SMART CCD
diffractometer
1074 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.060
Graphite monochromatorθmax = 27.5°, θmin = 2.4°
Detector resolution: not relevant pixels mm-1h = 88
ω scansk = 2116
5018 measured reflectionsl = 88
1657 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)] = 0.055Hydrogen site location: difference Fourier map
wR(F2) = 0.122All H-atom parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.0376P)2 + 0.2197P]
where P = (Fo2 + 2Fc2)/3
1657 reflections(Δ/σ)max = 0.001
131 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.24 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
O10.4972 (2)0.38506 (9)0.5079 (2)0.0274 (4)
O20.2961 (2)0.45098 (9)0.1289 (2)0.0216 (4)
HA0.360 (5)0.4335 (18)0.237 (5)0.059 (10)*
C10.0925 (3)0.41199 (14)0.1794 (3)0.0215 (5)
H1A0.013 (3)0.4514 (13)0.157 (3)0.026 (6)*
H1B0.021 (3)0.3653 (13)0.246 (3)0.024 (6)*
C20.2469 (3)0.44804 (14)0.3163 (3)0.0228 (5)
H2A0.184 (4)0.4621 (15)0.460 (4)0.045 (7)*
H2B0.304 (4)0.4972 (15)0.251 (4)0.033 (7)*
C30.4263 (3)0.39445 (12)0.3407 (3)0.0191 (5)
C40.5206 (3)0.35429 (14)0.1475 (3)0.0208 (5)
H4A0.617 (4)0.3136 (14)0.187 (3)0.029 (6)*
H4B0.598 (3)0.3968 (13)0.075 (3)0.025 (6)*
C50.3612 (3)0.32087 (13)0.0117 (3)0.0199 (5)
H5A0.433 (4)0.3040 (14)0.127 (4)0.033 (6)*
H5B0.289 (3)0.2733 (13)0.077 (3)0.020 (6)*
C60.1996 (3)0.38333 (12)0.0280 (3)0.0183 (5)
C70.0450 (3)0.35136 (13)0.1602 (3)0.0228 (5)
C80.0786 (4)0.33061 (15)0.2714 (4)0.0307 (6)
H80.178 (4)0.3135 (17)0.364 (4)0.056 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0269 (8)0.0399 (10)0.0158 (8)0.0013 (7)0.0050 (6)0.0005 (7)
O20.0262 (8)0.0234 (8)0.0149 (8)0.0020 (6)0.0006 (6)0.0030 (6)
C10.0207 (11)0.0266 (12)0.0169 (10)0.0034 (9)0.0005 (9)0.0008 (9)
C20.0265 (12)0.0276 (13)0.0143 (10)0.0037 (10)0.0025 (9)0.0033 (9)
C30.0211 (10)0.0204 (11)0.0161 (11)0.0041 (8)0.0040 (8)0.0023 (8)
C40.0210 (11)0.0254 (12)0.0160 (10)0.0041 (9)0.0010 (9)0.0008 (9)
C50.0250 (11)0.0191 (11)0.0153 (10)0.0009 (9)0.0009 (9)0.0014 (9)
C60.0202 (10)0.0200 (11)0.0147 (10)0.0013 (8)0.0025 (8)0.0008 (8)
C70.0239 (11)0.0275 (12)0.0167 (10)0.0003 (9)0.0004 (9)0.0004 (9)
C80.0285 (13)0.0405 (14)0.0234 (11)0.0053 (11)0.0039 (10)0.0012 (11)
Geometric parameters (Å, º) top
O1—C31.231 (2)C3—C41.507 (3)
O2—C61.436 (2)C4—C51.537 (3)
O2—HA0.84 (3)C4—H4A0.99 (2)
C1—C21.535 (3)C4—H4B0.98 (2)
C1—C61.537 (3)C5—C61.535 (3)
C1—H1A0.98 (2)C5—H5A1.02 (2)
C1—H1B1.00 (2)C5—H5B1.01 (2)
C2—C31.505 (3)C6—C71.490 (3)
C2—H2A1.01 (3)C7—C81.188 (3)
C2—H2B0.99 (2)C8—H80.97 (3)
C6—O2—HA105 (2)C5—C4—H4A112.4 (13)
C2—C1—C6111.21 (17)C3—C4—H4B102.9 (13)
C2—C1—H1A109.0 (13)C5—C4—H4B110.2 (12)
C6—C1—H1A110.9 (13)H4A—C4—H4B109.0 (19)
C2—C1—H1B111.8 (12)C6—C5—C4111.07 (17)
C6—C1—H1B106.7 (13)C6—C5—H5A108.2 (13)
H1A—C1—H1B107.2 (19)C4—C5—H5A109.2 (13)
C3—C2—C1112.66 (18)C6—C5—H5B108.6 (12)
C3—C2—H2A107.5 (15)C4—C5—H5B111.7 (11)
C1—C2—H2A113.0 (14)H5A—C5—H5B108.0 (17)
C3—C2—H2B106.6 (14)O2—C6—C7108.69 (16)
C1—C2—H2B109.2 (13)O2—C6—C5110.21 (17)
H2A—C2—H2B107 (2)C7—C6—C5111.31 (17)
O1—C3—C2122.32 (19)O2—C6—C1107.02 (17)
O1—C3—C4121.10 (19)C7—C6—C1109.92 (17)
C2—C3—C4116.55 (17)C5—C6—C1109.59 (17)
C3—C4—C5113.34 (18)C8—C7—C6175.7 (2)
C3—C4—H4A108.6 (13)C7—C8—H8179.2 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—HA···O1i0.84 (3)1.99 (3)2.820 (2)175 (3)
C1—H1A···O2ii0.98 (2)2.51 (2)3.482 (3)175.4 (18)
C8—H8···O1iii0.97 (3)2.65 (3)3.373 (3)132 (2)
Symmetry codes: (i) x, y, z+1; (ii) x, y+1, z; (iii) x1, y, z+1.
(II) 4-ethynyl-4-hydroxy-2,3,4,5-tetramethylcyclohexa-2,5-diene-1-one top
Crystal data top
C12H14O2F(000) = 816
Mr = 190.23Dx = 1.206 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.020 (2) ÅCell parameters from 999 reflections
b = 14.010 (3) Åθ = 5.1–24.0°
c = 16.612 (3) ŵ = 0.08 mm1
β = 93.56 (3)°T = 150 K
V = 2095.2 (7) Å3Block, colourless
Z = 80.35 × 0.25 × 0.20 mm
Data collection top
Bruker SMART CCD
diffractometer
4796 independent reflections
Radiation source: fine-focus sealed tube3037 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: not relevant pixels mm-1θmax = 27.5°, θmin = 1.9°
ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1817
Tmin = 0.802, Tmax = 1.000l = 2121
14728 measured 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)] = 0.052Hydrogen site location: difference Fourier map
wR(F2) = 0.145H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0752P)2 + 0.3548P]
where P = (Fo2 + 2Fc2)/3
4796 reflections(Δ/σ)max < 0.001
329 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.21 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
C10.4469 (3)0.18776 (17)0.29582 (14)0.0412 (6)
H10.447 (3)0.214 (2)0.3473 (19)0.077 (9)*
C20.4521 (2)0.15847 (14)0.22992 (12)0.0315 (5)
C30.4614 (2)0.12292 (12)0.14593 (11)0.0245 (4)
O10.45510 (16)0.20655 (9)0.09553 (9)0.0315 (3)
H1A0.470 (3)0.190 (2)0.0491 (18)0.062 (9)*
C40.3264 (2)0.06088 (14)0.12465 (11)0.0275 (4)
C50.1791 (3)0.10929 (19)0.13290 (16)0.0393 (5)
H5A0.115 (3)0.096 (2)0.0844 (18)0.067 (9)*
H5B0.126 (3)0.085 (2)0.180 (2)0.083 (10)*
H5C0.190 (3)0.179 (2)0.1393 (17)0.066 (8)*
C60.3409 (2)0.02932 (14)0.09933 (11)0.0277 (4)
C70.2113 (3)0.09396 (18)0.07707 (16)0.0472 (6)
H7A0.22350.15310.10590.094 (11)*
H7B0.20690.10620.02010.103 (12)*
H7C0.12090.06370.09100.114 (13)*
C80.4884 (2)0.07056 (13)0.09038 (11)0.0264 (4)
O20.50047 (17)0.15168 (9)0.06234 (8)0.0347 (4)
C90.6232 (2)0.01494 (13)0.11358 (11)0.0267 (4)
C100.7680 (3)0.06559 (19)0.10501 (17)0.0414 (6)
H10A0.780 (4)0.083 (2)0.050 (2)0.087 (10)*
H10B0.845 (4)0.034 (2)0.1294 (19)0.080 (10)*
H10C0.765 (4)0.130 (3)0.128 (2)0.097 (12)*
C110.6119 (2)0.07511 (13)0.13995 (11)0.0267 (4)
C120.7428 (2)0.13775 (16)0.16262 (15)0.0417 (6)
H12A0.70870.19720.18350.101 (12)*
H12B0.79730.14970.11580.143 (17)*
H12C0.80610.10650.20310.136 (16)*
C210.0034 (2)0.27725 (15)0.27480 (13)0.0341 (5)
H210.007 (3)0.2317 (17)0.3176 (15)0.049 (7)*
C220.0059 (2)0.33843 (13)0.22580 (11)0.0262 (4)
C230.0118 (2)0.41234 (12)0.16210 (11)0.0233 (4)
O210.00239 (16)0.50329 (9)0.20260 (8)0.0297 (3)
H21A0.013 (3)0.544 (2)0.1624 (17)0.063 (8)*
C240.1634 (2)0.40601 (13)0.11764 (11)0.0249 (4)
C250.2928 (3)0.42295 (18)0.16894 (15)0.0359 (5)
H25A0.347 (3)0.478 (2)0.1522 (19)0.077 (9)*
H25B0.364 (4)0.367 (2)0.160 (2)0.091 (11)*
H25C0.263 (3)0.428 (2)0.222 (2)0.072 (9)*
C260.1790 (2)0.38688 (12)0.03851 (11)0.0254 (4)
C270.3273 (2)0.37967 (17)0.00778 (14)0.0387 (5)
H27A0.38250.43740.00090.134 (16)*
H27B0.38160.32660.01200.17 (2)*
H27C0.31260.37050.06400.157 (18)*
C280.0462 (2)0.37392 (12)0.00783 (11)0.0250 (4)
O220.06202 (17)0.36239 (9)0.08191 (8)0.0338 (4)
C290.1033 (2)0.37620 (12)0.03273 (11)0.0252 (4)
C300.2294 (3)0.35622 (17)0.02003 (14)0.0350 (5)
H30A0.229 (3)0.291 (2)0.0441 (19)0.087 (10)*
H30B0.322 (4)0.359 (2)0.008 (2)0.076 (10)*
H30C0.225 (3)0.395 (2)0.0673 (18)0.065 (8)*
C310.1215 (2)0.39679 (12)0.11152 (11)0.0236 (4)
C320.2695 (2)0.40597 (16)0.15749 (13)0.0338 (5)
H32A0.30220.47110.15600.122 (14)*
H32B0.34050.36570.13340.138 (16)*
H32C0.26020.38700.21250.150 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0584 (15)0.0385 (13)0.0272 (11)0.0011 (11)0.0055 (11)0.0050 (9)
C20.0390 (12)0.0254 (10)0.0301 (11)0.0007 (9)0.0033 (9)0.0004 (8)
C30.0316 (10)0.0197 (9)0.0224 (9)0.0021 (8)0.0024 (8)0.0010 (7)
O10.0456 (9)0.0230 (7)0.0262 (8)0.0056 (6)0.0050 (7)0.0029 (6)
C40.0291 (10)0.0324 (10)0.0213 (9)0.0004 (8)0.0038 (8)0.0014 (8)
C50.0288 (12)0.0474 (15)0.0424 (14)0.0064 (10)0.0074 (10)0.0049 (11)
C60.0310 (10)0.0301 (10)0.0223 (9)0.0051 (8)0.0038 (8)0.0013 (8)
C70.0486 (14)0.0454 (14)0.0484 (15)0.0196 (12)0.0100 (12)0.0075 (12)
C80.0415 (11)0.0212 (9)0.0166 (8)0.0003 (8)0.0035 (8)0.0045 (7)
O20.0567 (9)0.0217 (7)0.0263 (7)0.0019 (6)0.0064 (7)0.0008 (6)
C90.0314 (10)0.0282 (10)0.0203 (9)0.0060 (8)0.0003 (8)0.0034 (7)
C100.0382 (13)0.0413 (14)0.0439 (14)0.0159 (11)0.0052 (11)0.0045 (11)
C110.0303 (10)0.0265 (10)0.0229 (9)0.0017 (8)0.0011 (8)0.0021 (7)
C120.0330 (12)0.0379 (13)0.0533 (15)0.0053 (10)0.0034 (11)0.0078 (11)
C210.0465 (13)0.0291 (11)0.0265 (10)0.0066 (9)0.0007 (9)0.0036 (9)
C220.0301 (10)0.0273 (10)0.0212 (9)0.0018 (8)0.0015 (8)0.0027 (8)
C230.0295 (10)0.0203 (9)0.0202 (9)0.0010 (7)0.0029 (8)0.0017 (7)
O210.0433 (8)0.0217 (7)0.0247 (7)0.0025 (6)0.0061 (6)0.0038 (6)
C240.0267 (10)0.0213 (9)0.0270 (10)0.0018 (7)0.0045 (8)0.0022 (7)
C250.0324 (12)0.0406 (13)0.0357 (12)0.0024 (10)0.0096 (10)0.0012 (10)
C260.0289 (10)0.0194 (9)0.0277 (10)0.0020 (7)0.0013 (8)0.0007 (7)
C270.0346 (12)0.0428 (13)0.0376 (13)0.0048 (10)0.0056 (10)0.0015 (10)
C280.0397 (11)0.0128 (8)0.0227 (9)0.0003 (7)0.0037 (8)0.0005 (7)
O220.0515 (9)0.0278 (7)0.0222 (7)0.0012 (6)0.0020 (6)0.0036 (6)
C290.0331 (10)0.0166 (9)0.0265 (10)0.0034 (7)0.0072 (8)0.0014 (7)
C300.0386 (13)0.0350 (12)0.0328 (12)0.0093 (10)0.0140 (10)0.0011 (10)
C310.0282 (10)0.0171 (9)0.0255 (9)0.0007 (7)0.0027 (8)0.0033 (7)
C320.0280 (11)0.0363 (12)0.0369 (12)0.0008 (9)0.0001 (9)0.0014 (9)
Geometric parameters (Å, º) top
C1—C21.173 (3)C21—C221.181 (3)
C1—H10.93 (3)C21—H210.96 (3)
C2—C31.489 (3)C22—C231.479 (3)
C3—O11.439 (2)C23—O211.443 (2)
C3—C41.520 (3)C23—C241.516 (3)
C3—C111.523 (3)C23—C311.524 (3)
O1—H1A0.82 (3)O21—H21A0.89 (3)
C4—C61.341 (3)C24—C261.340 (3)
C4—C51.505 (3)C24—C251.507 (3)
C5—H5A0.98 (3)C25—H25A0.95 (3)
C5—H5B1.00 (3)C25—H25B1.02 (4)
C5—H5C0.99 (3)C25—H25C0.91 (3)
C6—C81.467 (3)C26—C281.475 (3)
C6—C71.507 (3)C26—C271.504 (3)
C7—H7A0.9600C27—H27A0.9600
C7—H7B0.9600C27—H27B0.9600
C7—H7C0.9600C27—H27C0.9600
C8—O21.236 (2)C28—O221.241 (2)
C8—C91.475 (3)C28—C291.470 (3)
C9—C111.341 (3)C29—C311.340 (3)
C9—C101.501 (3)C29—C301.504 (3)
C10—H10A0.96 (4)C30—H30A1.00 (3)
C10—H10B0.90 (3)C30—H30B0.93 (3)
C10—H10C0.98 (4)C30—H30C0.96 (3)
C11—C121.500 (3)C31—C321.502 (3)
C12—H12A0.9600C32—H32A0.9600
C12—H12B0.9600C32—H32B0.9600
C12—H12C0.9600C32—H32C0.9600
C2—C1—H1176.5 (19)C22—C21—H21174.5 (15)
C1—C2—C3178.7 (2)C21—C22—C23177.7 (2)
O1—C3—C2105.69 (14)O21—C23—C22106.64 (14)
O1—C3—C4109.15 (15)O21—C23—C24109.26 (15)
C2—C3—C4108.55 (16)C22—C23—C24107.37 (15)
O1—C3—C11108.86 (15)O21—C23—C31109.47 (14)
C2—C3—C11108.10 (16)C22—C23—C31107.46 (15)
C4—C3—C11115.99 (15)C24—C23—C31116.20 (15)
C3—O1—H1A108 (2)C23—O21—H21A103.4 (18)
C6—C4—C5123.88 (19)C26—C24—C25123.24 (19)
C6—C4—C3121.27 (17)C26—C24—C23121.76 (17)
C5—C4—C3114.84 (18)C25—C24—C23115.01 (17)
C4—C5—H5A108.7 (16)C24—C25—H25A111.3 (18)
C4—C5—H5B112.3 (18)C24—C25—H25B107.4 (19)
H5A—C5—H5B107 (2)H25A—C25—H25B106 (3)
C4—C5—H5C111.8 (16)C24—C25—H25C111.8 (19)
H5A—C5—H5C109 (2)H25A—C25—H25C110 (3)
H5B—C5—H5C108 (2)H25B—C25—H25C110 (3)
C4—C6—C8120.69 (18)C24—C26—C28119.80 (17)
C4—C6—C7123.61 (19)C24—C26—C27123.42 (18)
C8—C6—C7115.69 (18)C28—C26—C27116.76 (17)
C6—C7—H7A109.5C26—C27—H27A109.5
C6—C7—H7B109.5C26—C27—H27B109.5
H7A—C7—H7B109.5H27A—C27—H27B109.5
C6—C7—H7C109.5C26—C27—H27C109.5
H7A—C7—H7C109.5H27A—C27—H27C109.5
H7B—C7—H7C109.5H27B—C27—H27C109.5
O2—C8—C6120.14 (18)O22—C28—C29120.22 (17)
O2—C8—C9119.62 (18)O22—C28—C26119.12 (18)
C6—C8—C9120.24 (16)C29—C28—C26120.66 (16)
C11—C9—C8120.28 (17)C31—C29—C28120.34 (17)
C11—C9—C10124.0 (2)C31—C29—C30123.93 (19)
C8—C9—C10115.68 (18)C28—C29—C30115.72 (17)
C9—C10—H10A111 (2)C29—C30—H30A114.7 (18)
C9—C10—H10B112 (2)C29—C30—H30B113 (2)
H10A—C10—H10B115 (3)H30A—C30—H30B103 (2)
C9—C10—H10C111 (2)C29—C30—H30C112.3 (17)
H10A—C10—H10C98 (3)H30A—C30—H30C101 (2)
H10B—C10—H10C108 (3)H30B—C30—H30C112 (2)
C9—C11—C12123.91 (18)C29—C31—C32124.46 (18)
C9—C11—C3121.40 (17)C29—C31—C23121.09 (17)
C12—C11—C3114.65 (17)C32—C31—C23114.45 (16)
C11—C12—H12A109.5C31—C32—H32A109.5
C11—C12—H12B109.5C31—C32—H32B109.5
H12A—C12—H12B109.5H32A—C32—H32B109.5
C11—C12—H12C109.5C31—C32—H32C109.5
H12A—C12—H12C109.5H32A—C32—H32C109.5
H12B—C12—H12C109.5H32B—C32—H32C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2i0.82 (3)1.96 (3)2.786 (2)179 (3)
O21—H21A···O22ii0.89 (3)1.94 (3)2.826 (2)172 (2)
C1—H1···O2iii0.93 (3)2.44 (3)3.271 (3)149 (2)
C21—H21···O22iv0.96 (3)2.21 (3)3.151 (3)168 (2)
C12—H12C···O21v0.962.683.634 (3)171
C32—H32B···O10.962.553.447 (3)155
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x+1, y+1/2, z+1/2; (iv) x, y+1/2, z+1/2; (v) x+1, y1/2, z+1/2.
 

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