1,2-Dihydro-1,6-dimethyl­phenanthro[1,2-b]furan-10,11-dione hemihydrate

Du, Z.-Y.; Qin, J.-K.; Mao, X.-P.; Ma, L.; Gu, L.-Q.

doi:10.1107/S1600536805025365

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1,2-Dihydro-1,6-dimethylphenanthro[1,2-b]furan-10,11-dione hemihydrate

Z.-Y. Du, J.-K. Qin, X.-P. Mao, L. Ma and L.-Q. Gu

In the title compound, C₁₈H₁₄O₃·0.5H₂O, also known as dihydrotanshinone hemihydrate, the molecular skeleton is a nearly planar. The two molecules in the asymmetric unit are linked by O—H

O hydrogen bonds involving the carbonyl groups and the solvent water molecule, forming moieties which are, in turn, linked via intermolecular π–π stacking interactions into a two-dimensional sheet.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025365/ac6189sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025365/ac6189Isup2.hkl Contains datablock I

CCDC reference: 283740

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.036
wR factor = 0.104
Data-to-parameter ratio = 7.1

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are meaningless.
           From the CIF: _refine_ls_abs_structure_Flack    0.000
           From the CIF: _refine_ls_abs_structure_Flack_su   10.000
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ...      10.00
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.10
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C33
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C34
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C8     -C14           1.44 Ang.
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C26    -C32           1.44 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range          C8     -C14           0.21 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range          C26    -C32           0.22 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C11    -   C12    ...       1.56 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C29    -   C30    ...       1.56 Ang.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C18
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C18 H14 O3
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..      10.00

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           25.99
           From the CIF: _reflns_number_total               2782
           Count of symmetry unique reflns         2797
           Completeness (_total/calc)             99.46%
           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
   0 ALERT level B = Potentially serious problem
  22 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1,2-Dihydro-1,6-dimethylphenanthro[1,2-b]furan-10,11-dione hemihydrate top

Crystal data top

C₁₈H₁₄O₃·0.5H₂O	F(000) = 604
M_r = 287.30	D_x = 1.358 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.287 (2) Å	Cell parameters from 984 reflections
b = 26.569 (9) Å	θ = 2.9–26.2°
c = 7.294 (3) Å	µ = 0.09 mm⁻¹
β = 95.590 (7)°	T = 293 K
V = 1405.6 (8) Å³	Plate, red
Z = 4	0.48 × 0.42 × 0.17 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	2782 independent reflections
Radiation source: fine-focus sealed tube	1958 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 26.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→8
T_min = 0.956, T_max = 0.984	k = −32→32
7831 measured reflections	l = −8→8

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0558P)² + 0.1165P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
2782 reflections	Δρ_max = 0.16 e Å⁻³
392 parameters	Δρ_min = −0.15 e Å⁻³
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0 (10)

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

	x	y	z	U_iso*/U_eq
C1	0.9253 (5)	0.91392 (13)	0.8099 (4)	0.0513 (9)
H1	0.8437	0.8884	0.7695	0.062*
C2	0.8662 (6)	0.96308 (15)	0.8064 (5)	0.0646 (11)
H2	0.7438	0.9705	0.7679	0.077*
C3	0.9896 (6)	1.00237 (14)	0.8605 (5)	0.0610 (10)
H3	0.9479	1.0355	0.8534	0.073*
C4	1.1670 (5)	0.99307 (13)	0.9225 (4)	0.0525 (9)
C5	1.2327 (4)	0.94229 (12)	0.9327 (4)	0.0449 (8)
C6	1.4157 (5)	0.93134 (14)	0.9974 (5)	0.0521 (9)
H6	1.4953	0.9577	1.0334	0.062*
C7	1.4799 (5)	0.88369 (13)	1.0090 (5)	0.0513 (9)
H7	1.6020	0.8777	1.0530	0.062*
C8	1.3631 (4)	0.84312 (12)	0.9551 (4)	0.0440 (8)
C9	1.1807 (4)	0.85157 (12)	0.8857 (4)	0.0417 (8)
C10	1.1100 (4)	0.90174 (12)	0.8750 (4)	0.0425 (8)
C11	1.0691 (5)	0.80678 (13)	0.8224 (4)	0.0473 (8)
C12	1.1563 (5)	0.75316 (14)	0.8398 (5)	0.0517 (8)
C13	1.3413 (5)	0.74957 (13)	0.9162 (5)	0.0510 (8)
C14	1.4336 (4)	0.79210 (13)	0.9683 (4)	0.0483 (8)
C15	1.6465 (6)	0.73087 (16)	1.0269 (7)	0.0729 (11)
H15A	1.6923	0.7180	1.1472	0.088*
H15B	1.7387	0.7248	0.9422	0.088*
C16	1.4635 (5)	0.70471 (14)	0.9578 (5)	0.0611 (10)
H16	1.4782	0.6861	0.8442	0.073*
C17	1.3957 (6)	0.66965 (15)	1.1009 (5)	0.0778 (12)
H17A	1.2728	0.6587	1.0609	0.117*
H17B	1.3957	0.6871	1.2161	0.117*
H17C	1.4758	0.6410	1.1164	0.117*
C18	1.2953 (6)	1.03576 (15)	0.9780 (6)	0.0745 (11)
H18A	1.2298	1.0671	0.9623	0.112*
H18B	1.3960	1.0356	0.9024	0.112*
H18C	1.3421	1.0319	1.1049	0.112*
C19	0.5556 (4)	0.39037 (13)	0.4989 (5)	0.0494 (8)
H19	0.4729	0.4158	0.4608	0.059*
C20	0.4989 (5)	0.34120 (13)	0.4926 (5)	0.0555 (9)
H20	0.3771	0.3338	0.4513	0.067*
C21	0.6192 (5)	0.30211 (13)	0.5465 (4)	0.0546 (9)
H21	0.5764	0.2691	0.5387	0.066*
C22	0.7987 (5)	0.31099 (11)	0.6106 (4)	0.0457 (8)
C23	0.8635 (4)	0.36207 (11)	0.6212 (4)	0.0395 (7)
C24	1.0461 (4)	0.37291 (12)	0.6855 (4)	0.0464 (8)
H24	1.1259	0.3465	0.7205	0.056*
C25	1.1102 (4)	0.42086 (12)	0.6981 (4)	0.0455 (8)
H25	1.2319	0.4270	0.7432	0.055*
C26	0.9942 (4)	0.46086 (11)	0.6437 (4)	0.0394 (8)
C27	0.8121 (4)	0.45307 (10)	0.5748 (4)	0.0381 (7)
C28	0.7408 (4)	0.40262 (12)	0.5637 (4)	0.0389 (7)
C29	0.7002 (5)	0.49820 (12)	0.5137 (4)	0.0458 (8)
C30	0.7888 (5)	0.55148 (13)	0.5329 (5)	0.0530 (9)
C31	0.9761 (5)	0.55435 (12)	0.6059 (5)	0.0482 (8)
C32	1.0658 (4)	0.51196 (12)	0.6577 (4)	0.0432 (7)
C33	1.2737 (6)	0.57297 (15)	0.7351 (7)	0.0834 (13)
H33A	1.3819	0.5808	0.6730	0.100*
H33B	1.2944	0.5847	0.8614	0.100*
C34	1.1044 (5)	0.59857 (13)	0.6376 (5)	0.0588 (10)
H34	1.0537	0.6227	0.7210	0.071*
C35	1.1462 (7)	0.62484 (17)	0.4641 (7)	0.0953 (14)
H35A	1.0332	0.6360	0.3979	0.143*
H35B	1.2077	0.6020	0.3886	0.143*
H35C	1.2243	0.6533	0.4948	0.143*
C36	0.9276 (5)	0.26849 (12)	0.6692 (5)	0.0595 (9)
H36A	0.8617	0.2372	0.6581	0.089*
H36B	0.9764	0.2734	0.7950	0.089*
H36C	1.0269	0.2678	0.5920	0.089*
O1	1.6074 (3)	0.78468 (10)	1.0377 (3)	0.0608 (7)
O2	1.0582 (4)	0.71746 (10)	0.7862 (4)	0.0745 (8)
O3	0.9118 (3)	0.80813 (10)	0.7532 (4)	0.0728 (8)
O4	1.2403 (3)	0.51878 (9)	0.7312 (3)	0.0601 (7)
O5	0.6899 (4)	0.58736 (9)	0.4869 (4)	0.0820 (9)
O6	0.5427 (3)	0.49676 (9)	0.4470 (4)	0.0743 (8)
O7	0.6965 (4)	0.69888 (13)	0.5430 (5)	0.1033 (10)
H7A	0.7069	0.6655	0.5482	0.155*
H7B	0.7741	0.7109	0.6328	0.155*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.046 (2)	0.061 (2)	0.0463 (19)	−0.0040 (17)	−0.0026 (15)	0.0045 (16)
C2	0.054 (2)	0.075 (3)	0.063 (3)	0.006 (2)	−0.0043 (19)	0.004 (2)
C3	0.074 (3)	0.055 (2)	0.053 (2)	0.004 (2)	0.0022 (19)	0.0044 (18)
C4	0.061 (2)	0.057 (2)	0.0383 (19)	−0.0050 (17)	0.0015 (16)	−0.0005 (15)
C5	0.052 (2)	0.054 (2)	0.0299 (16)	−0.0085 (17)	0.0075 (14)	0.0001 (14)
C6	0.046 (2)	0.056 (2)	0.053 (2)	−0.0150 (17)	−0.0017 (17)	−0.0052 (17)
C7	0.0406 (19)	0.061 (2)	0.051 (2)	−0.0069 (17)	−0.0020 (16)	−0.0033 (17)
C8	0.0395 (19)	0.058 (2)	0.0345 (17)	−0.0079 (16)	0.0038 (15)	−0.0003 (15)
C9	0.0413 (19)	0.053 (2)	0.0311 (16)	−0.0071 (16)	0.0039 (14)	0.0039 (14)
C10	0.0423 (19)	0.056 (2)	0.0293 (16)	−0.0072 (16)	0.0048 (14)	0.0019 (14)
C11	0.0437 (19)	0.057 (2)	0.0399 (18)	−0.0117 (17)	−0.0012 (15)	0.0022 (15)
C12	0.051 (2)	0.058 (2)	0.0459 (19)	−0.0114 (18)	0.0017 (16)	−0.0038 (17)
C13	0.049 (2)	0.056 (2)	0.0469 (19)	−0.0058 (18)	0.0016 (16)	−0.0028 (16)
C14	0.0415 (19)	0.062 (2)	0.0415 (19)	−0.0036 (17)	0.0043 (15)	−0.0022 (16)
C15	0.058 (3)	0.067 (3)	0.093 (3)	0.008 (2)	0.001 (2)	−0.004 (2)
C16	0.057 (2)	0.063 (2)	0.063 (2)	0.0017 (19)	0.0037 (18)	−0.0127 (19)
C17	0.086 (3)	0.060 (2)	0.087 (3)	0.004 (2)	0.004 (2)	0.003 (2)
C18	0.089 (3)	0.058 (2)	0.075 (3)	−0.012 (2)	0.001 (2)	−0.007 (2)
C19	0.0407 (19)	0.057 (2)	0.0495 (19)	−0.0014 (16)	−0.0028 (15)	−0.0004 (15)
C20	0.046 (2)	0.062 (2)	0.057 (2)	−0.0123 (18)	−0.0045 (16)	−0.0058 (18)
C21	0.064 (2)	0.050 (2)	0.050 (2)	−0.0154 (19)	0.0025 (17)	−0.0026 (17)
C22	0.056 (2)	0.0438 (19)	0.0377 (17)	−0.0031 (16)	0.0074 (15)	−0.0021 (14)
C23	0.0441 (18)	0.0405 (17)	0.0341 (16)	0.0013 (15)	0.0057 (14)	−0.0012 (13)
C24	0.0441 (19)	0.0441 (19)	0.0499 (19)	0.0047 (15)	−0.0015 (15)	0.0042 (15)
C25	0.0377 (18)	0.0457 (19)	0.051 (2)	−0.0011 (15)	−0.0060 (15)	0.0041 (15)
C26	0.0416 (19)	0.0419 (17)	0.0348 (17)	−0.0014 (15)	0.0051 (14)	0.0021 (14)
C27	0.0394 (18)	0.0426 (18)	0.0326 (16)	0.0036 (14)	0.0058 (14)	−0.0004 (13)
C28	0.0425 (18)	0.0445 (17)	0.0302 (16)	−0.0017 (14)	0.0060 (13)	−0.0027 (13)
C29	0.042 (2)	0.047 (2)	0.0477 (19)	0.0044 (16)	0.0028 (16)	−0.0010 (15)
C30	0.057 (2)	0.0434 (19)	0.058 (2)	0.0063 (18)	0.0035 (17)	0.0025 (17)
C31	0.053 (2)	0.0387 (17)	0.054 (2)	−0.0012 (16)	0.0073 (16)	0.0011 (15)
C32	0.0411 (18)	0.0430 (19)	0.0454 (18)	0.0019 (15)	0.0039 (14)	0.0006 (15)
C33	0.072 (3)	0.048 (2)	0.125 (4)	−0.013 (2)	−0.017 (3)	0.002 (2)
C34	0.061 (2)	0.0396 (19)	0.076 (3)	−0.0051 (17)	0.007 (2)	−0.0038 (17)
C35	0.103 (3)	0.073 (3)	0.110 (4)	−0.025 (3)	0.012 (3)	0.022 (2)
C36	0.071 (2)	0.0404 (19)	0.067 (2)	−0.0029 (17)	0.0037 (19)	0.0004 (16)
O1	0.0405 (13)	0.0660 (16)	0.0743 (16)	0.0007 (11)	−0.0030 (12)	−0.0069 (13)
O2	0.0639 (17)	0.0598 (16)	0.097 (2)	−0.0121 (14)	−0.0092 (14)	−0.0149 (14)
O3	0.0497 (16)	0.0655 (17)	0.098 (2)	−0.0121 (14)	−0.0192 (14)	0.0028 (15)
O4	0.0461 (13)	0.0454 (14)	0.0858 (18)	−0.0047 (11)	−0.0089 (12)	0.0034 (12)
O5	0.0678 (18)	0.0456 (16)	0.128 (2)	0.0107 (14)	−0.0128 (17)	0.0098 (15)
O6	0.0479 (16)	0.0583 (16)	0.111 (2)	0.0082 (13)	−0.0192 (14)	−0.0024 (15)
O7	0.096 (2)	0.085 (2)	0.124 (3)	0.0087 (18)	−0.0129 (19)	−0.0055 (18)

Geometric parameters (Å, º) top

C1—C2	1.375 (5)	C19—C28	1.424 (4)
C1—C10	1.420 (4)	C19—H19	0.9300
C1—H1	0.9300	C20—C21	1.391 (5)
C2—C3	1.409 (5)	C20—H20	0.9300
C2—H2	0.9300	C21—C22	1.366 (4)
C3—C4	1.350 (5)	C21—H21	0.9300
C3—H3	0.9300	C22—C23	1.436 (4)
C4—C5	1.431 (5)	C22—C36	1.504 (5)
C4—C18	1.500 (5)	C23—C24	1.397 (4)
C5—C6	1.401 (5)	C23—C28	1.436 (4)
C5—C10	1.437 (4)	C24—C25	1.357 (4)
C6—C7	1.349 (5)	C24—H24	0.9300
C6—H6	0.9300	C25—C26	1.391 (4)
C7—C8	1.406 (4)	C25—H25	0.9300
C7—H7	0.9300	C26—C27	1.388 (4)
C8—C9	1.394 (4)	C26—C32	1.455 (4)
C8—C14	1.450 (5)	C27—C28	1.437 (4)
C9—C10	1.428 (5)	C27—C29	1.493 (4)
C9—C11	1.489 (4)	C29—O6	1.203 (4)
C11—O3	1.208 (4)	C29—C30	1.556 (5)
C11—C12	1.560 (5)	C30—O5	1.222 (4)
C12—O2	1.229 (4)	C30—C31	1.418 (5)
C12—C13	1.411 (5)	C31—C32	1.338 (4)
C13—C14	1.351 (5)	C31—C34	1.505 (5)
C13—C16	1.501 (5)	C32—O4	1.343 (4)
C14—O1	1.331 (4)	C33—O4	1.460 (5)
C15—O1	1.461 (5)	C33—C34	1.523 (5)
C15—C16	1.544 (6)	C33—H33A	0.9700
C15—H15A	0.9700	C33—H33B	0.9700
C15—H15B	0.9700	C34—C35	1.502 (5)
C16—C17	1.517 (5)	C34—H34	0.9800
C16—H16	0.9800	C35—H35A	0.9600
C17—H17A	0.9600	C35—H35B	0.9600
C17—H17B	0.9600	C35—H35C	0.9600
C17—H17C	0.9600	C36—H36A	0.9600
C18—H18A	0.9600	C36—H36B	0.9600
C18—H18B	0.9600	C36—H36C	0.9600
C18—H18C	0.9600	O7—H7A	0.8917
C19—C20	1.370 (5)	O7—H7B	0.8824

C2—C1—C10	120.5 (3)	C28—C19—H19	119.9
C2—C1—H1	119.8	C19—C20—C21	121.5 (3)
C10—C1—H1	119.8	C19—C20—H20	119.2
C1—C2—C3	120.6 (4)	C21—C20—H20	119.2
C1—C2—H2	119.7	C22—C21—C20	121.6 (3)
C3—C2—H2	119.7	C22—C21—H21	119.2
C4—C3—C2	121.5 (3)	C20—C21—H21	119.2
C4—C3—H3	119.3	C21—C22—C23	118.7 (3)
C2—C3—H3	119.3	C21—C22—C36	121.2 (3)
C3—C4—C5	119.6 (3)	C23—C22—C36	120.1 (3)
C3—C4—C18	120.2 (3)	C24—C23—C28	119.3 (3)
C5—C4—C18	120.2 (3)	C24—C23—C22	120.7 (3)
C6—C5—C4	121.0 (3)	C28—C23—C22	120.1 (3)
C6—C5—C10	119.2 (3)	C25—C24—C23	121.8 (3)
C4—C5—C10	119.8 (3)	C25—C24—H24	119.1
C7—C6—C5	121.9 (3)	C23—C24—H24	119.1
C7—C6—H6	119.1	C24—C25—C26	120.1 (3)
C5—C6—H6	119.1	C24—C25—H25	119.9
C6—C7—C8	120.4 (3)	C26—C25—H25	119.9
C6—C7—H7	119.8	C27—C26—C25	121.5 (3)
C8—C7—H7	119.8	C27—C26—C32	119.2 (3)
C9—C8—C7	120.5 (3)	C25—C26—C32	119.3 (3)
C9—C8—C14	119.6 (3)	C26—C27—C28	119.1 (3)
C7—C8—C14	119.8 (3)	C26—C27—C29	117.6 (3)
C8—C9—C10	119.7 (3)	C28—C27—C29	123.3 (3)
C8—C9—C11	117.1 (3)	C19—C28—C23	117.9 (3)
C10—C9—C11	123.1 (3)	C19—C28—C27	123.9 (3)
C1—C10—C9	123.7 (3)	C23—C28—C27	118.2 (3)
C1—C10—C5	118.0 (3)	O6—C29—C27	124.5 (3)
C9—C10—C5	118.2 (3)	O6—C29—C30	115.9 (3)
O3—C11—C9	125.0 (3)	C27—C29—C30	119.6 (3)
O3—C11—C12	115.1 (3)	O5—C30—C31	125.5 (3)
C9—C11—C12	119.9 (3)	O5—C30—C29	117.1 (3)
O2—C12—C13	125.3 (4)	C31—C30—C29	117.3 (3)
O2—C12—C11	117.3 (3)	C32—C31—C30	119.1 (3)
C13—C12—C11	117.4 (3)	C32—C31—C34	109.6 (3)
C14—C13—C12	119.0 (3)	C30—C31—C34	131.3 (3)
C14—C13—C16	109.8 (3)	C31—C32—O4	114.6 (3)
C12—C13—C16	131.2 (3)	C31—C32—C26	127.1 (3)
O1—C14—C13	114.3 (3)	O4—C32—C26	118.2 (3)
O1—C14—C8	118.8 (3)	O4—C33—C34	107.8 (3)
C13—C14—C8	126.9 (3)	O4—C33—H33A	110.2
O1—C15—C16	106.9 (3)	C34—C33—H33A	110.2
O1—C15—H15A	110.3	O4—C33—H33B	110.2
C16—C15—H15A	110.3	C34—C33—H33B	110.2
O1—C15—H15B	110.3	H33A—C33—H33B	108.5
C16—C15—H15B	110.3	C35—C34—C31	114.0 (3)
H15A—C15—H15B	108.6	C35—C34—C33	112.3 (4)
C13—C16—C17	113.6 (3)	C31—C34—C33	100.7 (3)
C13—C16—C15	100.7 (3)	C35—C34—H34	109.8
C17—C16—C15	112.4 (3)	C31—C34—H34	109.8
C13—C16—H16	110.0	C33—C34—H34	109.8
C17—C16—H16	110.0	C34—C35—H35A	109.5
C15—C16—H16	110.0	C34—C35—H35B	109.5
C16—C17—H17A	109.5	H35A—C35—H35B	109.5
C16—C17—H17B	109.5	C34—C35—H35C	109.5
H17A—C17—H17B	109.5	H35A—C35—H35C	109.5
C16—C17—H17C	109.5	H35B—C35—H35C	109.5
H17A—C17—H17C	109.5	C22—C36—H36A	109.5
H17B—C17—H17C	109.5	C22—C36—H36B	109.5
C4—C18—H18A	109.5	H36A—C36—H36B	109.5
C4—C18—H18B	109.5	C22—C36—H36C	109.5
H18A—C18—H18B	109.5	H36A—C36—H36C	109.5
C4—C18—H18C	109.5	H36B—C36—H36C	109.5
H18A—C18—H18C	109.5	C14—O1—C15	107.9 (3)
H18B—C18—H18C	109.5	C32—O4—C33	106.9 (3)
C20—C19—C28	120.2 (3)	H7A—O7—H7B	106.4
C20—C19—H19	119.9

C10—C1—C2—C3	2.4 (6)	C20—C21—C22—C36	179.8 (3)
C1—C2—C3—C4	−2.0 (6)	C21—C22—C23—C24	−179.8 (3)
C2—C3—C4—C5	0.4 (5)	C36—C22—C23—C24	0.1 (5)
C2—C3—C4—C18	179.6 (4)	C21—C22—C23—C28	−0.5 (4)
C3—C4—C5—C6	−179.6 (3)	C36—C22—C23—C28	179.5 (3)
C18—C4—C5—C6	1.2 (5)	C28—C23—C24—C25	1.2 (5)
C3—C4—C5—C10	0.7 (5)	C22—C23—C24—C25	−179.5 (3)
C18—C4—C5—C10	−178.5 (3)	C23—C24—C25—C26	−1.0 (5)
C4—C5—C6—C7	179.6 (3)	C24—C25—C26—C27	−0.4 (5)
C10—C5—C6—C7	−0.7 (5)	C24—C25—C26—C32	−179.8 (3)
C5—C6—C7—C8	0.2 (5)	C25—C26—C27—C28	1.6 (4)
C6—C7—C8—C9	1.2 (5)	C32—C26—C27—C28	−179.1 (3)
C6—C7—C8—C14	−180.0 (3)	C25—C26—C27—C29	−177.8 (3)
C7—C8—C9—C10	−2.1 (5)	C32—C26—C27—C29	1.5 (4)
C14—C8—C9—C10	179.1 (3)	C20—C19—C28—C23	0.0 (5)
C7—C8—C9—C11	176.8 (3)	C20—C19—C28—C27	179.9 (3)
C14—C8—C9—C11	−2.0 (4)	C24—C23—C28—C19	180.0 (3)
C2—C1—C10—C9	178.9 (3)	C22—C23—C28—C19	0.7 (4)
C2—C1—C10—C5	−1.3 (5)	C24—C23—C28—C27	0.0 (4)
C8—C9—C10—C1	−178.7 (3)	C22—C23—C28—C27	−179.3 (3)
C11—C9—C10—C1	2.5 (5)	C26—C27—C28—C19	178.7 (3)
C8—C9—C10—C5	1.5 (4)	C29—C27—C28—C19	−2.0 (5)
C11—C9—C10—C5	−177.3 (3)	C26—C27—C28—C23	−1.3 (4)
C6—C5—C10—C1	−180.0 (3)	C29—C27—C28—C23	178.0 (3)
C4—C5—C10—C1	−0.3 (4)	C26—C27—C29—O6	178.0 (3)
C6—C5—C10—C9	−0.1 (4)	C28—C27—C29—O6	−1.4 (5)
C4—C5—C10—C9	179.5 (3)	C26—C27—C29—C30	−1.2 (4)
C8—C9—C11—O3	−177.2 (3)	C28—C27—C29—C30	179.4 (3)
C10—C9—C11—O3	1.6 (5)	O6—C29—C30—O5	3.2 (5)
C8—C9—C11—C12	1.5 (4)	C27—C29—C30—O5	−177.6 (3)
C10—C9—C11—C12	−179.7 (3)	O6—C29—C30—C31	−178.2 (3)
O3—C11—C12—O2	−1.4 (5)	C27—C29—C30—C31	1.1 (4)
C9—C11—C12—O2	179.7 (3)	O5—C30—C31—C32	177.2 (4)
O3—C11—C12—C13	178.7 (3)	C29—C30—C31—C32	−1.4 (5)
C9—C11—C12—C13	−0.2 (4)	O5—C30—C31—C34	−3.5 (6)
O2—C12—C13—C14	179.5 (3)	C29—C30—C31—C34	177.9 (3)
C11—C12—C13—C14	−0.6 (5)	C30—C31—C32—O4	−177.7 (3)
O2—C12—C13—C16	−2.1 (6)	C34—C31—C32—O4	2.9 (4)
C11—C12—C13—C16	177.8 (3)	C30—C31—C32—C26	1.8 (5)
C12—C13—C14—O1	−179.7 (3)	C34—C31—C32—C26	−177.6 (3)
C16—C13—C14—O1	1.6 (4)	C27—C26—C32—C31	−1.9 (5)
C12—C13—C14—C8	0.1 (5)	C25—C26—C32—C31	177.4 (3)
C16—C13—C14—C8	−178.7 (3)	C27—C26—C32—O4	177.5 (3)
C9—C8—C14—O1	−178.9 (3)	C25—C26—C32—O4	−3.1 (4)
C7—C8—C14—O1	2.2 (5)	C32—C31—C34—C35	114.7 (4)
C9—C8—C14—C13	1.4 (5)	C30—C31—C34—C35	−64.7 (5)
C7—C8—C14—C13	−177.5 (3)	C32—C31—C34—C33	−5.8 (4)
C14—C13—C16—C17	115.5 (4)	C30—C31—C34—C33	174.8 (4)
C12—C13—C16—C17	−63.0 (5)	O4—C33—C34—C35	−115.1 (4)
C14—C13—C16—C15	−4.8 (4)	O4—C33—C34—C31	6.6 (4)
C12—C13—C16—C15	176.7 (4)	C13—C14—O1—C15	2.6 (4)
O1—C15—C16—C13	6.1 (4)	C8—C14—O1—C15	−177.1 (3)
O1—C15—C16—C17	−115.0 (4)	C16—C15—O1—C14	−5.6 (4)
C28—C19—C20—C21	−0.7 (5)	C31—C32—O4—C33	1.7 (4)
C19—C20—C21—C22	0.9 (6)	C26—C32—O4—C33	−177.9 (3)
C20—C21—C22—C23	−0.3 (5)	C34—C33—O4—C32	−5.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O5	0.89	2.12	2.991 (4)	164
O7—H7B···O2	0.88	2.26	3.070 (4)	152

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