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The title compound [systematic name: (1RS,3RS)-1,11-dihydroxy-8-meth­oxy-3-methyl-1,2,3,4-tetra­hydro­benz[a]anthracene-7,11-dione], C20H18O5, crystallizes with two molecules in the asymmetric unit. Each mol­ecule exhibits a curvature of the anthraquinone ring system and possesses two intra­molecular C=O...H—O hydrogen bonds. Pairs of enanti­omers form π-stacked dimers, with this inter­action supported by inter­molecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049099/fl2077sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049099/fl2077Isup2.hkl
Contains datablock I

CCDC reference: 629676

Key indicators

  • Single-crystal X-ray study
  • T = 85 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.046
  • wR factor = 0.121
  • Data-to-parameter ratio = 20.1

checkCIF/PLATON results

No syntax errors found




Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.61 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.69 e/A    PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C32 .. 3.01 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: APEX2; program(s) used to refine structure: APEX2; molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: enCIFer (Version 1.1; Allen et al., 2004).

(1R*,3R*)-1,11-dihydroxy-8-methoxy-3-methyl-1,2,3,4- tetrahydrobenz[a]anthracene-7,11-dione top
Crystal data top
C20H18O5F(000) = 1424
Mr = 338.34Dx = 1.430 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.273 (3) ÅCell parameters from 1558 reflections
b = 17.066 (3) Åθ = 1.4–33.3°
c = 12.958 (3) ŵ = 0.10 mm1
β = 95.25 (3)°T = 85 K
V = 3143.2 (11) Å3Rod, red
Z = 80.49 × 0.12 × 0.12 mm
Data collection top
Bruker Kappa-APEXII area-detector
diffractometer
9162 independent reflections
Radiation source: fine-focus sealed tube7375 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 33.3°, θmin = 1.4°
Absorption correction: multi-scan
(APEX2; Bruker, 2004)
h = 2021
Tmin = 0.985, Tmax = 0.988k = 2525
81294 measured reflectionsl = 1414
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0498P)2 + 1.8289P]
where P = (Fo2 + 2Fc2)/3
9162 reflections(Δ/σ)max < 0.001
455 parametersΔρmax = 0.69 e Å3
0 restraintsΔρmin = 0.27 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
C10.38871 (10)0.51144 (8)0.27834 (11)0.0242 (3)
H1A0.44080.54900.28650.029*
O10.30124 (7)0.55321 (6)0.27134 (9)0.0293 (2)
H10.30420.59070.23220.044*
C20.38669 (10)0.46393 (8)0.37766 (12)0.0261 (3)
H2A0.39450.49910.43670.031*
H2B0.32580.43880.37820.031*
C30.46309 (10)0.40180 (9)0.38875 (12)0.0276 (3)
H3A0.52400.42660.38120.033*
C130.46657 (12)0.36218 (10)0.49509 (13)0.0342 (3)
H13A0.51520.32310.50030.051*
H13B0.40700.33790.50320.051*
H13C0.47970.40070.54840.051*
C40.44223 (10)0.34328 (8)0.30146 (11)0.0242 (3)
H4A0.38890.31150.31670.029*
H4B0.49590.30870.29920.029*
C4A0.42090 (9)0.38039 (7)0.19555 (11)0.0199 (2)
C50.42287 (9)0.33184 (7)0.10876 (11)0.0229 (3)
H5A0.43690.27900.11850.027*
C60.40459 (9)0.36008 (7)0.00901 (11)0.0222 (3)
H6A0.40400.32620.04730.027*
C6A0.38708 (9)0.43992 (7)0.00659 (11)0.0195 (2)
C70.37008 (9)0.46740 (8)0.11715 (11)0.0216 (3)
O70.37623 (8)0.42051 (6)0.18753 (8)0.0336 (3)
C7A0.34723 (8)0.55145 (7)0.13596 (10)0.0194 (2)
C80.31780 (9)0.58037 (8)0.23540 (11)0.0214 (3)
O80.30292 (7)0.52878 (6)0.31562 (8)0.0264 (2)
C140.25652 (11)0.55834 (9)0.41086 (12)0.0304 (3)
H14A0.24960.51690.46100.046*
H14B0.29340.59980.43670.046*
H14C0.19560.57810.39850.046*
C90.30260 (9)0.66141 (8)0.24878 (11)0.0234 (3)
H9A0.28450.68090.31460.028*
C100.31407 (9)0.71233 (8)0.16615 (11)0.0242 (3)
H10A0.30510.76580.17720.029*
C110.33898 (9)0.68464 (7)0.06590 (11)0.0216 (3)
O110.34524 (8)0.73781 (6)0.01178 (8)0.0282 (2)
H110.36300.71600.06650.042*
C11A0.35556 (8)0.60362 (7)0.05009 (10)0.0193 (2)
C120.37870 (9)0.57583 (7)0.05696 (11)0.0200 (2)
O120.39250 (7)0.62469 (6)0.12830 (8)0.0268 (2)
C12A0.38633 (8)0.49056 (7)0.07924 (10)0.0191 (2)
C12B0.39911 (9)0.46054 (7)0.18252 (10)0.0195 (2)
C210.09534 (9)0.82540 (7)0.61628 (10)0.0169 (2)
H210.03680.83160.64950.020*
O210.17337 (7)0.82676 (5)0.69424 (7)0.0222 (2)
H21A0.16460.86060.73720.033*
C220.09783 (9)0.74365 (7)0.56898 (10)0.0200 (2)
H22B0.16160.73200.55350.024*
H22A0.08030.70550.61930.024*
C230.03195 (9)0.73574 (7)0.47033 (10)0.0188 (2)
H230.03130.75240.48460.023*
C330.02741 (10)0.65131 (7)0.43086 (11)0.0250 (3)
H33C0.00430.61790.48250.038*
H33B0.08920.63450.41700.038*
H33A0.01410.64850.36830.038*
C240.06802 (8)0.79056 (7)0.38962 (10)0.0173 (2)
H24B0.12380.76760.36440.021*
H24A0.02050.79460.33130.021*
C24A0.09186 (8)0.87216 (7)0.42986 (10)0.0155 (2)
C250.10347 (8)0.93054 (7)0.35585 (10)0.0162 (2)
H250.09550.91770.28580.019*
C260.12652 (8)1.00662 (7)0.38458 (10)0.0161 (2)
H260.13691.04390.33450.019*
C26A0.13413 (8)1.02718 (6)0.48936 (9)0.0140 (2)
C270.15743 (8)1.11114 (7)0.51495 (9)0.0152 (2)
O270.16925 (8)1.15618 (5)0.44366 (7)0.0249 (2)
C27A0.16391 (8)1.13608 (6)0.62474 (9)0.0145 (2)
C280.19019 (8)1.21269 (7)0.65591 (10)0.0156 (2)
O280.21473 (6)1.26447 (5)0.58309 (7)0.01876 (18)
C340.23969 (10)1.34262 (7)0.61717 (11)0.0249 (3)
H34C0.25561.37320.55910.037*
H34B0.29271.34050.66830.037*
H34A0.18741.36630.64680.037*
C290.18924 (9)1.23405 (7)0.76077 (10)0.0190 (2)
H290.20751.28440.78150.023*
C300.16180 (9)1.18180 (7)0.83311 (10)0.0202 (2)
H300.16051.19750.90170.024*
C310.13582 (9)1.10510 (7)0.80425 (10)0.0183 (2)
O310.11083 (8)1.05753 (5)0.88082 (7)0.0256 (2)
H310.09501.01470.85640.038*
C31A0.13778 (8)1.08144 (7)0.70034 (9)0.0151 (2)
C320.11271 (8)0.99984 (7)0.67267 (9)0.0148 (2)
O320.08246 (7)0.95643 (5)0.73960 (7)0.01963 (18)
C32B0.10205 (8)0.89081 (6)0.53614 (9)0.0143 (2)
C32A0.11913 (8)0.97073 (6)0.56534 (9)0.0137 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0284 (6)0.0199 (6)0.0238 (7)0.0030 (5)0.0011 (5)0.0006 (5)
O10.0317 (5)0.0245 (5)0.0321 (6)0.0072 (4)0.0055 (4)0.0029 (4)
C20.0257 (6)0.0272 (6)0.0254 (8)0.0023 (5)0.0024 (5)0.0023 (5)
C30.0262 (7)0.0291 (7)0.0271 (8)0.0019 (5)0.0006 (5)0.0047 (6)
C130.0388 (8)0.0369 (8)0.0268 (8)0.0066 (6)0.0021 (6)0.0092 (6)
C40.0246 (6)0.0214 (6)0.0265 (8)0.0024 (5)0.0021 (5)0.0070 (5)
C4A0.0173 (5)0.0176 (5)0.0244 (7)0.0012 (4)0.0001 (4)0.0031 (5)
C50.0226 (6)0.0158 (5)0.0296 (8)0.0009 (4)0.0005 (5)0.0022 (5)
C60.0231 (6)0.0175 (5)0.0251 (7)0.0011 (4)0.0021 (5)0.0012 (5)
C6A0.0180 (5)0.0174 (5)0.0225 (7)0.0002 (4)0.0024 (4)0.0007 (5)
C70.0210 (6)0.0195 (5)0.0232 (7)0.0017 (4)0.0037 (5)0.0004 (5)
O70.0492 (7)0.0247 (5)0.0247 (6)0.0092 (5)0.0082 (5)0.0027 (4)
C7A0.0160 (5)0.0189 (5)0.0229 (7)0.0006 (4)0.0003 (4)0.0029 (5)
C80.0177 (5)0.0232 (6)0.0231 (7)0.0000 (4)0.0013 (5)0.0034 (5)
O80.0325 (5)0.0251 (5)0.0205 (5)0.0039 (4)0.0029 (4)0.0028 (4)
C140.0389 (8)0.0301 (7)0.0212 (8)0.0066 (6)0.0032 (6)0.0037 (6)
C90.0203 (6)0.0249 (6)0.0245 (7)0.0012 (5)0.0000 (5)0.0083 (5)
C100.0202 (6)0.0193 (6)0.0328 (8)0.0012 (4)0.0016 (5)0.0076 (5)
C110.0190 (5)0.0180 (5)0.0277 (7)0.0002 (4)0.0020 (5)0.0022 (5)
O110.0381 (6)0.0170 (4)0.0290 (6)0.0014 (4)0.0010 (4)0.0015 (4)
C11A0.0166 (5)0.0166 (5)0.0243 (7)0.0001 (4)0.0001 (4)0.0027 (5)
C120.0187 (5)0.0172 (5)0.0236 (7)0.0003 (4)0.0004 (5)0.0017 (5)
O120.0368 (5)0.0180 (4)0.0249 (5)0.0015 (4)0.0011 (4)0.0008 (4)
C12A0.0169 (5)0.0162 (5)0.0234 (7)0.0000 (4)0.0021 (4)0.0017 (5)
C12B0.0179 (5)0.0180 (5)0.0221 (7)0.0003 (4)0.0013 (4)0.0008 (5)
C210.0221 (5)0.0129 (5)0.0155 (6)0.0002 (4)0.0000 (4)0.0004 (4)
O210.0282 (5)0.0178 (4)0.0192 (5)0.0028 (3)0.0044 (4)0.0004 (3)
C220.0253 (6)0.0140 (5)0.0206 (7)0.0018 (4)0.0009 (5)0.0003 (4)
C230.0211 (6)0.0151 (5)0.0205 (7)0.0007 (4)0.0032 (4)0.0025 (4)
C330.0349 (7)0.0162 (5)0.0244 (7)0.0038 (5)0.0048 (5)0.0043 (5)
C240.0204 (5)0.0149 (5)0.0168 (6)0.0011 (4)0.0028 (4)0.0040 (4)
C24A0.0151 (5)0.0142 (5)0.0171 (6)0.0005 (4)0.0017 (4)0.0018 (4)
C250.0188 (5)0.0178 (5)0.0119 (6)0.0001 (4)0.0017 (4)0.0021 (4)
C260.0188 (5)0.0155 (5)0.0140 (6)0.0003 (4)0.0023 (4)0.0006 (4)
C26A0.0150 (5)0.0123 (5)0.0147 (6)0.0012 (4)0.0012 (4)0.0000 (4)
C270.0185 (5)0.0128 (5)0.0143 (6)0.0016 (4)0.0011 (4)0.0001 (4)
O270.0456 (6)0.0148 (4)0.0149 (5)0.0032 (4)0.0055 (4)0.0015 (3)
C27A0.0171 (5)0.0126 (5)0.0134 (6)0.0023 (4)0.0001 (4)0.0003 (4)
C280.0175 (5)0.0137 (5)0.0154 (6)0.0011 (4)0.0002 (4)0.0002 (4)
O280.0270 (4)0.0129 (4)0.0163 (5)0.0039 (3)0.0012 (3)0.0005 (3)
C340.0351 (7)0.0153 (5)0.0245 (7)0.0079 (5)0.0037 (5)0.0037 (5)
C290.0239 (6)0.0147 (5)0.0178 (6)0.0018 (4)0.0018 (4)0.0029 (4)
C300.0297 (6)0.0181 (5)0.0123 (6)0.0034 (5)0.0002 (5)0.0034 (4)
C310.0265 (6)0.0158 (5)0.0127 (6)0.0031 (4)0.0018 (4)0.0009 (4)
O310.0464 (6)0.0178 (4)0.0133 (5)0.0012 (4)0.0075 (4)0.0002 (3)
C31A0.0186 (5)0.0127 (5)0.0139 (6)0.0024 (4)0.0011 (4)0.0002 (4)
C320.0176 (5)0.0136 (5)0.0130 (6)0.0026 (4)0.0005 (4)0.0009 (4)
O320.0289 (5)0.0161 (4)0.0144 (5)0.0002 (3)0.0048 (3)0.0018 (3)
C32B0.0147 (5)0.0130 (5)0.0151 (6)0.0013 (4)0.0013 (4)0.0004 (4)
C32A0.0150 (5)0.0131 (5)0.0130 (6)0.0011 (4)0.0012 (4)0.0003 (4)
Geometric parameters (Å, º) top
C1—O11.4332 (17)C21—O211.4337 (16)
C1—C21.5238 (19)C21—C221.5256 (17)
C1—C12B1.5337 (19)C21—C32B1.5336 (16)
C1—H1A0.9800C21—H210.9800
O1—H10.8200O21—H21A0.8200
C2—C31.518 (2)C22—C231.5219 (19)
C2—H2A0.9700C22—H22B0.9700
C2—H2B0.9700C22—H22A0.9700
C3—C41.518 (2)C23—C331.5283 (17)
C3—C131.532 (2)C23—C241.5274 (17)
C3—H3A0.9800C23—H230.9800
C13—H13A0.9600C33—H33C0.9600
C13—H13B0.9600C33—H33B0.9600
C13—H13C0.9600C33—H33A0.9600
C4—C4A1.5168 (19)C24—C24A1.5147 (16)
C4—H4A0.9700C24—H24B0.9700
C4—H4B0.9700C24—H24A0.9700
C4A—C51.3993 (19)C24A—C251.4033 (17)
C4A—C12B1.4096 (17)C24A—C32B1.4079 (17)
C5—C61.382 (2)C25—C261.3821 (16)
C5—H5A0.9300C25—H250.9300
C6—C6A1.3965 (17)C26—C26A1.3969 (17)
C6—H6A0.9300C26—H260.9300
C6A—C12A1.4094 (18)C26A—C32A1.4079 (16)
C6A—C71.5059 (19)C26A—C271.5011 (16)
C7—O71.2227 (17)C27—O271.2253 (15)
C7—C7A1.4861 (17)C27—C27A1.4798 (17)
C7A—C81.4076 (19)C27A—C281.4092 (16)
C7A—C11A1.4215 (19)C27A—C31A1.4266 (16)
C8—O81.3640 (17)C28—O281.3618 (15)
C8—C91.4082 (19)C28—C291.4081 (18)
O8—C141.4376 (17)O28—C341.4395 (15)
C14—H14A0.9600C34—H34C0.9600
C14—H14B0.9600C34—H34B0.9600
C14—H14C0.9600C34—H34A0.9600
C9—C101.377 (2)C29—C301.3765 (18)
C9—H9A0.9300C29—H290.9300
C10—C111.397 (2)C30—C311.4018 (17)
C10—H10A0.9300C30—H300.9300
C11—O111.3520 (17)C31—O311.3549 (15)
C11—C11A1.4146 (17)C31—C31A1.4085 (17)
O11—H110.8200O31—H310.8200
C11A—C121.4747 (19)C31A—C321.4739 (16)
C12—O121.2472 (16)C32—O321.2475 (15)
C12—C12A1.4855 (17)C32—C32A1.4876 (17)
C12A—C12B1.4290 (19)C32B—C32A1.4304 (16)
O1—C1—C2103.56 (11)O21—C21—C22104.64 (9)
O1—C1—C12B112.26 (11)O21—C21—C32B111.89 (10)
C2—C1—C12B113.15 (11)C22—C21—C32B112.86 (10)
O1—C1—H1A109.2O21—C21—H21109.1
C2—C1—H1A109.2C22—C21—H21109.1
C12B—C1—H1A109.2C32B—C21—H21109.1
C1—O1—H1109.5C21—O21—H21A109.5
C3—C2—C1112.49 (12)C23—C22—C21112.54 (10)
C3—C2—H2A109.1C23—C22—H22B109.1
C1—C2—H2A109.1C21—C22—H22B109.1
C3—C2—H2B109.1C23—C22—H22A109.1
C1—C2—H2B109.1C21—C22—H22A109.1
H2A—C2—H2B107.8H22B—C22—H22A107.8
C4—C3—C2107.39 (12)C22—C23—C33111.64 (11)
C4—C3—C13111.59 (12)C22—C23—C24107.44 (10)
C2—C3—C13110.93 (13)C33—C23—C24110.79 (10)
C4—C3—H3A109.0C22—C23—H23109.0
C2—C3—H3A109.0C33—C23—H23109.0
C13—C3—H3A109.0C24—C23—H23109.0
C3—C13—H13A109.5C23—C33—H33C109.5
C3—C13—H13B109.5C23—C33—H33B109.5
H13A—C13—H13B109.5H33C—C33—H33B109.5
C3—C13—H13C109.5C23—C33—H33A109.5
H13A—C13—H13C109.5H33C—C33—H33A109.5
H13B—C13—H13C109.5H33B—C33—H33A109.5
C3—C4—C4A114.14 (11)C24A—C24—C23113.99 (10)
C3—C4—H4A108.7C24A—C24—H24B108.8
C4A—C4—H4A108.7C23—C24—H24B108.8
C3—C4—H4B108.7C24A—C24—H24A108.8
C4A—C4—H4B108.7C23—C24—H24A108.8
H4A—C4—H4B107.6H24B—C24—H24A107.6
C5—C4A—C12B119.92 (12)C25—C24A—C32B119.99 (10)
C5—C4A—C4117.57 (11)C25—C24A—C24117.02 (11)
C12B—C4A—C4122.51 (12)C32B—C24A—C24122.99 (11)
C6—C5—C4A121.96 (12)C26—C25—C24A121.53 (11)
C6—C5—H5A119.0C26—C25—H25119.2
C4A—C5—H5A119.0C24A—C25—H25119.2
C5—C6—C6A119.45 (13)C25—C26—C26A119.56 (11)
C5—C6—H6A120.3C25—C26—H26120.2
C6A—C6—H6A120.3C26A—C26—H26120.2
C6—C6A—C12A119.89 (12)C26—C26A—C32A120.30 (10)
C6—C6A—C7116.91 (12)C26—C26A—C27116.78 (10)
C12A—C6A—C7123.19 (11)C32A—C26A—C27122.92 (11)
O7—C7—C7A122.62 (13)O27—C27—C27A122.93 (11)
O7—C7—C6A119.31 (12)O27—C27—C26A118.38 (11)
C7A—C7—C6A118.07 (11)C27A—C27—C26A118.69 (10)
C8—C7A—C11A119.57 (11)C28—C27A—C31A119.28 (11)
C8—C7A—C7122.09 (12)C28—C27A—C27122.28 (11)
C11A—C7A—C7118.34 (12)C31A—C27A—C27118.36 (10)
O8—C8—C7A118.93 (12)O28—C28—C27A118.82 (11)
O8—C8—C9121.92 (12)O28—C28—C29121.78 (11)
C7A—C8—C9119.13 (13)C27A—C28—C29119.40 (11)
C8—O8—C14117.07 (11)C28—O28—C34117.43 (10)
O8—C14—H14A109.5O28—C34—H34C109.5
O8—C14—H14B109.5O28—C34—H34B109.5
H14A—C14—H14B109.5H34C—C34—H34B109.5
O8—C14—H14C109.5O28—C34—H34A109.5
H14A—C14—H14C109.5H34C—C34—H34A109.5
H14B—C14—H14C109.5H34B—C34—H34A109.5
C10—C9—C8121.20 (13)C30—C29—C28121.20 (11)
C10—C9—H9A119.4C30—C29—H29119.4
C8—C9—H9A119.4C28—C29—H29119.4
C9—C10—C11120.77 (12)C29—C30—C31120.53 (12)
C9—C10—H10A119.6C29—C30—H30119.7
C11—C10—H10A119.6C31—C30—H30119.7
O11—C11—C10117.33 (12)O31—C31—C30116.43 (11)
O11—C11—C11A123.33 (12)O31—C31—C31A123.91 (11)
C10—C11—C11A119.34 (13)C30—C31—C31A119.65 (11)
C11—O11—H11109.5C31—O31—H31109.5
C11—C11A—C7A119.87 (12)C31—C31A—C27A119.90 (11)
C11—C11A—C12118.08 (12)C31—C31A—C32118.54 (11)
C7A—C11A—C12122.03 (11)C27A—C31A—C32121.56 (11)
O12—C12—C11A119.26 (11)O32—C32—C31A118.93 (11)
O12—C12—C12A120.47 (12)O32—C32—C32A120.43 (10)
C11A—C12—C12A120.26 (11)C31A—C32—C32A120.58 (10)
C6A—C12A—C12B120.64 (11)C24A—C32B—C32A118.31 (11)
C6A—C12A—C12116.95 (12)C24A—C32B—C21119.37 (10)
C12B—C12A—C12122.27 (12)C32A—C32B—C21122.32 (11)
C4A—C12B—C12A117.90 (12)C26A—C32A—C32B120.04 (11)
C4A—C12B—C1119.29 (12)C26A—C32A—C32116.85 (10)
C12A—C12B—C1122.79 (11)C32B—C32A—C32122.84 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11—H11···O120.821.782.5050 (14)146
O31—H31···O320.821.812.5207 (14)145
O1—H1···O120.822.012.6574 (16)135
O21—H21A···O320.822.012.6583 (13)135
O1—H1···O21i0.822.352.8620 (15)121
O21—H21A···O1ii0.822.452.8620 (15)112
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x, y+3/2, z+1/2.
 

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