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The title compound, (+)-10,13-dioxo-2α,4aβ,6aα,6bβ,9,9,12aβ-hepta­methyl-1,2,3,4,4a,5,6,6a,6b,7,8,8aα,9,10,11,12,12a,12bα,13,14bα-eicosa­hydro­picene-2β-carboxylic acid, C30H44O4, aggregates as carboxyl-to-ketone hydrogen-bonding catemers. Hydrogen bonds progress from the carboxyl group of one mol­ecule to the remote-ring ketone group of a translationally related neighbor in an adjoining cell connected by a common a cell-edge [O...O = 2.766 (3) Å and O—H...O = 163°], yielding chains that extend in the [011] direction. In the crystal structure, there are also four C—H...O close contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045788/lh2223sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045788/lh2223Isup2.hkl
Contains datablock I

CCDC reference: 630050

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.046
  • wR factor = 0.113
  • Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.91
Author Response: _diffrn_measured_fraction_theta_full Low .......0.91. (Alert level A). Even though we collected data out to 0.83 \%A, the crystal diffracted poorly beyond 0.88 \%A resolution, where more than 40% of the missing data lie. Larger crystals were not obtainable, and since the crystals of this compound are no longer available, we can only rely on the current data set.

Alert level B PLAT024_ALERT_4_B Merging of Friedel Pairs is STRONGLY Indicated . ! PLAT230_ALERT_2_B Hirshfeld Test Diff for C2 - C16 .. 7.94 su
Alert level C PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 0.30 PLAT230_ALERT_2_C Hirshfeld Test Diff for C6A - C18 .. 5.35 su PLAT412_ALERT_2_C Short Intra XH3 .. XHn H7A .. H18B .. 1.88 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A .. O2 .. 2.66 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H17C .. O3 .. 2.64 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H21B .. O4 .. 2.69 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
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 67.71 From the CIF: _reflns_number_total 3702 Count of symmetry unique reflns 2259 Completeness (_total/calc) 163.88% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1443 Fraction of Friedel pairs measured 0.639 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6B = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8A = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12B = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14B = . S
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 8 ALERT level G = General alerts; check 7 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 1 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

(+)-10,13-dioxo-2α,4aβ,6aα,6 bβ,9,9,12aβ-heptamethyl- 1,2,3,4,4a,5,6,6a,6 b,7,8,8aα,9,10,11,12,12a,12bα,13,14bα- eicosahydropicene-2β-carboxylic acid top
Crystal data top
C30H44O4Z = 1
Mr = 468.65F(000) = 256
Triclinic, P1Dx = 1.238 Mg m3
Hall symbol: P 1Melting point: 598 K
a = 6.6054 (2) ÅCu Kα radiation, λ = 1.54178 Å
b = 7.2228 (2) ÅCell parameters from 8622 reflections
c = 14.5495 (3) Åθ = 3.1–67.7°
α = 90.085 (2)°µ = 0.63 mm1
β = 96.287 (2)°T = 100 K
γ = 114.225 (2)°Parallelepiped, colourless
V = 628.39 (3) Å30.28 × 0.14 × 0.09 mm
Data collection top
Bruker SMART CCD APEX-II area-detector
diffractometer
3702 independent reflections
Radiation source: fine-focus sealed tube3345 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 67.7°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 77
Tmin = 0.843, Tmax = 0.945k = 88
8622 measured reflectionsl = 1717
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)] = 0.046H-atom parameters constrained
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0454P)2 + 0.3681P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3702 reflectionsΔρmax = 0.29 e Å3
315 parametersΔρmin = 0.20 e Å3
3 restraintsAbsolute structure: Flack (1983), 1651 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.2 (3)
Special details top

Experimental. 'crystal mounted on cryoloop using Paratone-N'

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
C11.0963 (6)0.3181 (5)0.8084 (2)0.0384 (8)
H1A0.99260.38220.78920.046*
H1B1.23830.39570.78270.046*
O11.2654 (4)0.0900 (3)0.13736 (15)0.0420 (6)
C21.1424 (5)0.3330 (5)0.9151 (2)0.0362 (8)
O21.0843 (4)0.4036 (3)0.47008 (14)0.0369 (5)
C30.9278 (6)0.1925 (5)0.9563 (2)0.0447 (9)
H3A0.96480.18711.02380.054*
H3B0.81650.25190.94720.054*
O31.1774 (4)0.6796 (4)0.90149 (16)0.0544 (7)
C40.8252 (6)0.0202 (5)0.9135 (2)0.0485 (10)
H4A0.68410.09810.93980.058*
H4B0.92790.08630.93050.058*
C4A0.7751 (5)0.0307 (5)0.8073 (2)0.0396 (8)
O41.2512 (4)0.5752 (4)1.03971 (15)0.0505 (7)
H41.24750.68381.05820.076*
C50.7100 (6)0.2479 (5)0.7720 (2)0.0445 (9)
H5A0.57300.33840.79800.053*
H5B0.83090.29020.79430.053*
C60.6679 (6)0.2742 (5)0.6663 (2)0.0414 (9)
H6A0.53360.25030.64480.050*
H6B0.63580.41640.64780.050*
C6A0.8666 (5)0.1293 (4)0.61690 (19)0.0277 (6)
C6B0.7869 (5)0.1274 (4)0.51001 (19)0.0274 (6)
C70.7242 (5)0.3363 (4)0.46163 (19)0.0289 (7)
H7A0.83910.38630.48360.035*
H7B0.58000.43300.48030.035*
C80.7034 (5)0.3363 (4)0.3564 (2)0.0313 (7)
H8A0.57940.29890.33310.038*
H8B0.66830.47450.33060.038*
C8A0.9209 (5)0.1856 (4)0.32446 (19)0.0287 (7)
H8A11.04130.21540.36030.034*
C90.9426 (5)0.2203 (4)0.21993 (19)0.0323 (7)
C101.1550 (5)0.0550 (4)0.19087 (18)0.0315 (7)
C111.2240 (5)0.1602 (4)0.2279 (2)0.0318 (7)
H11A1.13040.21960.19250.038*
H11B1.38140.24190.21800.038*
C121.2017 (5)0.1746 (4)0.33116 (18)0.0286 (7)
H12A1.23370.31700.34920.034*
H12B1.31520.13870.36730.034*
C12A0.9688 (5)0.0350 (4)0.35646 (19)0.0268 (7)
C12B0.9836 (5)0.0391 (4)0.46472 (18)0.0249 (6)
H12C1.11730.01100.48540.030*
C131.0356 (5)0.2455 (4)0.51112 (19)0.0291 (7)
C141.0400 (5)0.2501 (4)0.61213 (19)0.0308 (7)
H141.10030.37960.64420.037*
C14A0.9656 (5)0.0860 (4)0.66254 (19)0.0297 (7)
C14B0.9965 (5)0.1019 (5)0.7674 (2)0.0344 (7)
H14B1.10570.04260.78800.041*
C151.1923 (5)0.5472 (5)0.9484 (2)0.0373 (8)
C161.3405 (6)0.2824 (5)0.9505 (2)0.0421 (8)
H16A1.47620.37870.92700.063*
H16B1.30980.14390.92880.063*
H16C1.36200.29241.01840.063*
C170.5905 (6)0.0420 (6)0.7776 (2)0.0468 (9)
H17A0.57170.04690.71000.070*
H17B0.63230.17800.80580.070*
H17C0.44960.05250.79800.070*
C181.0542 (6)0.2055 (5)0.6326 (2)0.0417 (8)
H18A1.18740.11040.60700.062*
H18B1.00330.34020.60160.062*
H18C1.09080.21410.69910.062*
C190.5797 (5)0.0779 (5)0.4975 (2)0.0322 (7)
H19A0.54910.05200.43250.048*
H19B0.60810.04300.53650.048*
H19C0.45020.19330.51560.048*
C200.9524 (7)0.4273 (5)0.2079 (2)0.0520 (10)
H20A0.97220.44930.14360.078*
H20B0.81290.53500.22310.078*
H20C1.07850.42990.24940.078*
C210.7467 (6)0.2230 (5)0.1517 (2)0.0408 (8)
H21A0.74600.08760.15210.061*
H21B0.60560.32200.17010.061*
H21C0.76340.26110.08920.061*
C220.7943 (5)0.1076 (5)0.3114 (2)0.0315 (7)
H22A0.64640.00640.30380.047*
H22B0.83380.15910.25060.047*
H22C0.79140.21630.35090.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0376 (19)0.0403 (18)0.0318 (17)0.0094 (15)0.0095 (14)0.0001 (13)
O10.0504 (14)0.0424 (12)0.0333 (12)0.0170 (11)0.0138 (10)0.0023 (9)
C20.0300 (17)0.0441 (18)0.0280 (16)0.0089 (14)0.0041 (13)0.0020 (13)
O20.0513 (14)0.0302 (11)0.0290 (10)0.0151 (10)0.0101 (10)0.0041 (8)
C30.0382 (19)0.058 (2)0.0262 (15)0.0077 (16)0.0061 (14)0.0012 (14)
O30.0674 (19)0.0524 (15)0.0367 (13)0.0191 (13)0.0018 (12)0.0014 (11)
C40.040 (2)0.056 (2)0.0310 (17)0.0005 (16)0.0103 (15)0.0067 (15)
C4A0.0261 (17)0.055 (2)0.0250 (15)0.0031 (15)0.0072 (13)0.0039 (13)
O40.0661 (18)0.0614 (16)0.0320 (12)0.0359 (14)0.0007 (11)0.0104 (10)
C50.039 (2)0.049 (2)0.0306 (17)0.0018 (16)0.0064 (15)0.0132 (14)
C60.046 (2)0.0367 (17)0.0288 (16)0.0035 (15)0.0063 (15)0.0054 (12)
C6A0.0239 (15)0.0341 (15)0.0259 (14)0.0130 (13)0.0014 (12)0.0038 (11)
C6B0.0245 (16)0.0340 (14)0.0232 (13)0.0107 (12)0.0062 (12)0.0031 (11)
C70.0259 (16)0.0282 (15)0.0303 (15)0.0082 (12)0.0059 (12)0.0060 (11)
C80.0312 (17)0.0282 (14)0.0306 (15)0.0088 (13)0.0025 (12)0.0003 (11)
C8A0.0311 (17)0.0271 (14)0.0259 (14)0.0102 (12)0.0030 (12)0.0023 (11)
C90.043 (2)0.0281 (15)0.0258 (15)0.0134 (13)0.0070 (13)0.0006 (11)
C100.0399 (19)0.0363 (16)0.0198 (14)0.0173 (14)0.0030 (13)0.0032 (11)
C110.0366 (18)0.0293 (14)0.0265 (14)0.0090 (13)0.0100 (13)0.0045 (11)
C120.0346 (17)0.0274 (14)0.0233 (14)0.0121 (13)0.0049 (13)0.0031 (11)
C12A0.0275 (17)0.0296 (15)0.0257 (14)0.0136 (13)0.0057 (12)0.0017 (11)
C12B0.0215 (16)0.0277 (14)0.0224 (13)0.0075 (12)0.0003 (11)0.0036 (11)
C130.0261 (17)0.0306 (15)0.0294 (15)0.0099 (13)0.0056 (12)0.0023 (12)
C140.0263 (17)0.0338 (15)0.0288 (15)0.0085 (13)0.0050 (12)0.0030 (11)
C14A0.0207 (16)0.0407 (16)0.0242 (14)0.0088 (13)0.0043 (12)0.0027 (12)
C14B0.0287 (17)0.0423 (17)0.0264 (15)0.0087 (14)0.0046 (12)0.0035 (12)
C150.0293 (18)0.0515 (19)0.0287 (16)0.0138 (15)0.0047 (13)0.0014 (14)
C160.057 (2)0.0363 (17)0.0324 (16)0.0162 (16)0.0149 (15)0.0006 (13)
C170.0316 (18)0.065 (2)0.0332 (17)0.0074 (16)0.0126 (14)0.0052 (15)
C180.054 (2)0.0477 (19)0.0301 (16)0.0304 (17)0.0035 (15)0.0009 (13)
C190.0274 (16)0.0432 (17)0.0258 (14)0.0139 (14)0.0047 (12)0.0046 (12)
C200.077 (3)0.0356 (18)0.045 (2)0.0201 (18)0.0277 (19)0.0044 (15)
C210.0410 (19)0.0430 (18)0.0253 (15)0.0045 (15)0.0026 (13)0.0007 (12)
C220.0371 (17)0.0339 (15)0.0262 (14)0.0173 (13)0.0040 (12)0.0052 (11)
Geometric parameters (Å, º) top
C1—C14B1.515 (4)C8A—H8A11.0000
C1—C21.544 (4)C9—C101.527 (4)
C1—H1A0.9900C9—C201.534 (4)
C1—H1B0.9900C9—C211.536 (5)
O1—C101.215 (3)C10—C111.508 (4)
C2—C151.510 (4)C11—C121.533 (4)
C2—C161.535 (5)C11—H11A0.9900
C2—C31.551 (4)C11—H11B0.9900
O2—C131.227 (3)C12—C12A1.540 (4)
C3—C41.502 (5)C12—H12A0.9900
C3—H3A0.9900C12—H12B0.9900
C3—H3B0.9900C12A—C221.538 (4)
O3—C151.206 (4)C12A—C12B1.567 (4)
C4—C4A1.540 (4)C12B—C131.524 (4)
C4—H4A0.9900C12B—H12C1.0000
C4—H4B0.9900C13—C141.467 (4)
C4A—C51.519 (5)C14—C14A1.337 (4)
C4A—C171.536 (5)C14—H140.9500
C4A—C14B1.558 (4)C14A—C14B1.515 (4)
O4—C151.334 (4)C14B—H14B1.0000
O4—H40.8400C16—H16A0.9800
C5—C61.529 (4)C16—H16B0.9800
C5—H5A0.9900C16—H16C0.9800
C5—H5B0.9900C17—H17A0.9800
C6—C6A1.555 (4)C17—H17B0.9800
C6—H6A0.9900C17—H17C0.9800
C6—H6B0.9900C18—H18A0.9800
C6A—C14A1.534 (4)C18—H18B0.9800
C6A—C181.545 (5)C18—H18C0.9800
C6A—C6B1.588 (4)C19—H19A0.9800
C6B—C71.538 (4)C19—H19B0.9800
C6B—C191.543 (5)C19—H19C0.9800
C6B—C12B1.574 (3)C20—H20A0.9800
C7—C81.522 (4)C20—H20B0.9800
C7—H7A0.9900C20—H20C0.9800
C7—H7B0.9900C21—H21A0.9800
C8—C8A1.526 (4)C21—H21B0.9800
C8—H8A0.9900C21—H21C0.9800
C8—H8B0.9900C22—H22A0.9800
C8A—C12A1.552 (4)C22—H22B0.9800
C8A—C91.572 (4)C22—H22C0.9800
C14B—C1—C2113.5 (3)C10—C11—H11A108.9
C14B—C1—H1A108.9C12—C11—H11A108.9
C2—C1—H1A108.9C10—C11—H11B108.9
C14B—C1—H1B108.9C12—C11—H11B108.9
C2—C1—H1B108.9H11A—C11—H11B107.8
H1A—C1—H1B107.7C11—C12—C12A113.5 (2)
C15—C2—C16109.0 (3)C11—C12—H12A108.9
C15—C2—C1108.3 (3)C12A—C12—H12A108.9
C16—C2—C1112.5 (3)C11—C12—H12B108.9
C15—C2—C3106.3 (3)C12A—C12—H12B108.9
C16—C2—C3110.9 (3)H12A—C12—H12B107.7
C1—C2—C3109.6 (3)C22—C12A—C12109.5 (2)
C4—C3—C2113.2 (3)C22—C12A—C8A113.0 (2)
C4—C3—H3A108.9C12—C12A—C8A107.5 (2)
C2—C3—H3A108.9C22—C12A—C12B112.8 (2)
C4—C3—H3B108.9C12—C12A—C12B107.4 (2)
C2—C3—H3B108.9C8A—C12A—C12B106.2 (2)
H3A—C3—H3B107.7C13—C12B—C12A114.9 (2)
C3—C4—C4A113.8 (3)C13—C12B—C6B108.4 (2)
C3—C4—H4A108.8C12A—C12B—C6B118.0 (2)
C4A—C4—H4A108.8C13—C12B—H12C104.6
C3—C4—H4B108.8C12A—C12B—H12C104.6
C4A—C4—H4B108.8C6B—C12B—H12C104.6
H4A—C4—H4B107.7O2—C13—C14120.0 (3)
C5—C4A—C17111.6 (3)O2—C13—C12B124.2 (2)
C5—C4A—C4108.3 (3)C14—C13—C12B115.7 (2)
C17—C4A—C4110.9 (3)C14A—C14—C13125.0 (3)
C5—C4A—C14B106.4 (3)C14A—C14—H14117.5
C17—C4A—C14B111.4 (3)C13—C14—H14117.5
C4—C4A—C14B108.1 (2)C14—C14A—C14B122.0 (3)
C15—O4—H4109.5C14—C14A—C6A121.2 (2)
C4A—C5—C6112.9 (3)C14B—C14A—C6A116.5 (2)
C4A—C5—H5A109.0C1—C14B—C14A114.0 (2)
C6—C5—H5A109.0C1—C14B—C4A111.5 (3)
C4A—C5—H5B109.0C14A—C14B—C4A111.3 (2)
C6—C5—H5B109.0C1—C14B—H14B106.5
H5A—C5—H5B107.8C14A—C14B—H14B106.5
C5—C6—C6A113.9 (3)C4A—C14B—H14B106.5
C5—C6—H6A108.8O3—C15—O4122.1 (3)
C6A—C6—H6A108.8O3—C15—C2126.4 (3)
C5—C6—H6B108.8O4—C15—C2111.5 (3)
C6A—C6—H6B108.8C2—C16—H16A109.5
H6A—C6—H6B107.7C2—C16—H16B109.5
C14A—C6A—C18105.8 (2)H16A—C16—H16B109.5
C14A—C6A—C6110.8 (2)C2—C16—H16C109.5
C18—C6A—C6107.3 (3)H16A—C16—H16C109.5
C14A—C6A—C6B110.9 (2)H16B—C16—H16C109.5
C18—C6A—C6B112.0 (2)C4A—C17—H17A109.5
C6—C6A—C6B110.0 (2)C4A—C17—H17B109.5
C7—C6B—C19108.3 (2)H17A—C17—H17B109.5
C7—C6B—C12B109.6 (2)C4A—C17—H17C109.5
C19—C6B—C12B109.6 (2)H17A—C17—H17C109.5
C7—C6B—C6A110.5 (2)H17B—C17—H17C109.5
C19—C6B—C6A110.3 (2)C6A—C18—H18A109.5
C12B—C6B—C6A108.6 (2)C6A—C18—H18B109.5
C8—C7—C6B114.4 (2)H18A—C18—H18B109.5
C8—C7—H7A108.7C6A—C18—H18C109.5
C6B—C7—H7A108.7H18A—C18—H18C109.5
C8—C7—H7B108.7H18B—C18—H18C109.5
C6B—C7—H7B108.7C6B—C19—H19A109.5
H7A—C7—H7B107.6C6B—C19—H19B109.5
C7—C8—C8A110.5 (2)H19A—C19—H19B109.5
C7—C8—H8A109.6C6B—C19—H19C109.5
C8A—C8—H8A109.6H19A—C19—H19C109.5
C7—C8—H8B109.6H19B—C19—H19C109.5
C8A—C8—H8B109.6C9—C20—H20A109.5
H8A—C8—H8B108.1C9—C20—H20B109.5
C8—C8A—C12A110.7 (2)H20A—C20—H20B109.5
C8—C8A—C9113.9 (2)C9—C20—H20C109.5
C12A—C8A—C9116.1 (2)H20A—C20—H20C109.5
C8—C8A—H8A1105.0H20B—C20—H20C109.5
C12A—C8A—H8A1105.0C9—C21—H21A109.5
C9—C8A—H8A1105.0C9—C21—H21B109.5
C10—C9—C20109.0 (3)H21A—C21—H21B109.5
C10—C9—C21106.8 (2)C9—C21—H21C109.5
C20—C9—C21107.2 (3)H21A—C21—H21C109.5
C10—C9—C8A111.0 (2)H21B—C21—H21C109.5
C20—C9—C8A108.2 (2)C12A—C22—H22A109.5
C21—C9—C8A114.4 (3)C12A—C22—H22B109.5
O1—C10—C11119.4 (3)H22A—C22—H22B109.5
O1—C10—C9122.4 (3)C12A—C22—H22C109.5
C11—C10—C9118.2 (2)H22A—C22—H22C109.5
C10—C11—C12113.1 (2)H22B—C22—H22C109.5
C14B—C1—C2—C15167.8 (3)C8—C8A—C12A—C2265.1 (3)
C14B—C1—C2—C1671.6 (3)C9—C8A—C12A—C2266.8 (3)
C14B—C1—C2—C352.2 (4)C8—C8A—C12A—C12173.9 (2)
C15—C2—C3—C4167.1 (3)C9—C8A—C12A—C1254.2 (3)
C16—C2—C3—C474.5 (4)C8—C8A—C12A—C12B59.1 (3)
C1—C2—C3—C450.3 (4)C9—C8A—C12A—C12B169.0 (2)
C2—C3—C4—C4A54.6 (4)C22—C12A—C12B—C1357.0 (3)
C3—C4—C4A—C5170.5 (3)C12—C12A—C12B—C1363.8 (3)
C3—C4—C4A—C1766.7 (4)C8A—C12A—C12B—C13178.7 (3)
C3—C4—C4A—C14B55.7 (4)C22—C12A—C12B—C6B73.0 (3)
C17—C4A—C5—C660.6 (3)C12—C12A—C12B—C6B166.2 (2)
C4—C4A—C5—C6177.1 (3)C8A—C12A—C12B—C6B51.3 (3)
C14B—C4A—C5—C661.1 (4)C7—C6B—C12B—C13177.6 (2)
C4A—C5—C6—C6A55.0 (4)C19—C6B—C12B—C1358.9 (3)
C5—C6—C6A—C14A42.7 (4)C6A—C6B—C12B—C1361.7 (3)
C5—C6—C6A—C1872.3 (3)C7—C6B—C12B—C12A44.7 (3)
C5—C6—C6A—C6B165.7 (3)C19—C6B—C12B—C12A74.0 (3)
C14A—C6A—C6B—C7170.7 (3)C6A—C6B—C12B—C12A165.4 (2)
C18—C6A—C6B—C752.8 (3)C12A—C12B—C13—O26.8 (4)
C6—C6A—C6B—C766.3 (3)C6B—C12B—C13—O2141.4 (3)
C14A—C6A—C6B—C1969.6 (3)C12A—C12B—C13—C14177.3 (2)
C18—C6A—C6B—C19172.5 (3)C6B—C12B—C13—C1442.8 (3)
C6—C6A—C6B—C1953.4 (3)O2—C13—C14—C14A171.8 (3)
C14A—C6A—C6B—C12B50.6 (3)C12B—C13—C14—C14A12.2 (4)
C18—C6A—C6B—C12B67.3 (3)C13—C14—C14A—C14B173.8 (3)
C6—C6A—C6B—C12B173.5 (3)C13—C14—C14A—C6A0.3 (5)
C19—C6B—C7—C874.0 (3)C18—C6A—C14A—C14101.0 (3)
C12B—C6B—C7—C845.5 (3)C6—C6A—C14A—C14143.0 (3)
C6A—C6B—C7—C8165.1 (2)C6B—C6A—C14A—C1420.6 (4)
C6B—C7—C8—C8A57.2 (3)C18—C6A—C14A—C14B72.7 (3)
C7—C8—C8A—C12A64.4 (3)C6—C6A—C14A—C14B43.2 (4)
C7—C8—C8A—C9162.6 (2)C6B—C6A—C14A—C14B165.7 (2)
C8—C8A—C9—C10175.7 (3)C2—C1—C14B—C14A175.9 (3)
C12A—C8A—C9—C1045.4 (4)C2—C1—C14B—C4A57.0 (4)
C8—C8A—C9—C2064.7 (4)C14—C14A—C14B—C15.9 (4)
C12A—C8A—C9—C20165.0 (3)C6A—C14A—C14B—C1179.6 (3)
C8—C8A—C9—C2154.7 (3)C14—C14A—C14B—C4A133.0 (3)
C12A—C8A—C9—C2175.7 (3)C6A—C14A—C14B—C4A53.3 (4)
C20—C9—C10—O124.1 (4)C5—C4A—C14B—C1172.1 (3)
C21—C9—C10—O191.3 (3)C17—C4A—C14B—C166.0 (3)
C8A—C9—C10—O1143.3 (3)C4—C4A—C14B—C156.0 (4)
C20—C9—C10—C11158.0 (3)C5—C4A—C14B—C14A59.3 (4)
C21—C9—C10—C1186.5 (3)C17—C4A—C14B—C14A62.5 (3)
C8A—C9—C10—C1138.9 (4)C4—C4A—C14B—C14A175.4 (3)
O1—C10—C11—C12138.8 (3)C16—C2—C15—O3129.6 (4)
C9—C10—C11—C1243.3 (4)C1—C2—C15—O36.8 (5)
C10—C11—C12—C12A52.6 (4)C3—C2—C15—O3110.8 (4)
C11—C12—C12A—C2266.4 (3)C16—C2—C15—O452.3 (3)
C11—C12—C12A—C8A56.8 (3)C1—C2—C15—O4175.0 (3)
C11—C12—C12A—C12B170.8 (2)C3—C2—C15—O467.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O1i0.841.952.766 (3)163
C7—H7A···O2ii0.992.663.579 (4)155
C17—H17C···O3iii0.982.643.575 (4)159
C20—H20A···O4iv0.982.463.304 (4)144
C21—H21B···O4v0.982.693.225 (4)115
Symmetry codes: (i) x, y+1, z+1; (ii) x, y1, z; (iii) x1, y1, z; (iv) x, y1, z1; (v) x1, y1, z1.
 

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