Rotenone–acetic acid (2/1)

Yang, S.-P.; Chen, H.-M.; Zhang, F.; Chen, Q.-Q.; Yu, X.-B.; Huang, J.-G.; Xu, H.-H.

doi:10.1107/S1600536804004817

Rotenone-acetic acid (2/1)

S.-P. Yang, H.-M. Chen, F. Zhang, Q.-Q. Chen, X.-B. Yu, J.-G. Huang and H.-H. Xu

The structure determination of the title compound, a 2:1 adduct of rotenone and acetic acid, 2C₂₃H₂₂O₆·C₂H₄O₂, confirms that the rotenone molecule has an approximately V-shaped structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804004817/dn6123sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804004817/dn6123Isup2.hkl Contains datablock I

CCDC reference: 238774

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.060
wR factor = 0.146
Data-to-parameter ratio = 8.9

checkCIF/PLATON results

No syntax errors found



Alert level C
REFLT03_ALERT_1_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           28.30
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               5099
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         5439
           Completeness (_total/calc)             93.75%
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.63 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.34 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.53 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C19
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C42
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....        C47
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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           28.30
           From the CIF: _reflns_number_total               5099
           Count of symmetry unique reflns         5439
           Completeness (_total/calc)             93.75%
           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
  11 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SHELXTL (Sheldrick, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: SHELXTL.

Rotenone–acetic acid (2/1) top

Crystal data top

2C₂₃H₂₂O₆·C₂H₄O₂	F(000) = 896
M_r = 848.86	D_x = 1.334 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2045 reflections
a = 9.1356 (16) Å	θ = 5.1–39.9°
b = 15.359 (3) Å	µ = 0.10 mm⁻¹
c = 15.082 (3) Å	T = 293 K
β = 92.652 (4)°	Block, colourless
V = 2113.9 (7) Å³	0.51 × 0.20 × 0.06 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	5099 independent reflections
Radiation source: fine-focus sealed tube	3945 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
φ and ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→12
T_min = 0.952, T_max = 0.994	k = −20→10
12858 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.0596P)²] where P = (F_o² + 2F_c²)/3
5048 reflections	(Δ/σ)_max = 0.009
566 parameters	Δρ_max = 0.39 e Å⁻³
1 restraint	Δρ_min = −0.31 e Å⁻³

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
O1	0.9153 (5)	0.0213 (2)	0.3699 (2)	0.0682 (11)
O2	0.8380 (3)	0.27909 (19)	0.31431 (19)	0.0455 (8)
O3	0.8033 (3)	0.33043 (19)	0.4907 (2)	0.0474 (8)
O4	1.1258 (4)	0.2753 (2)	0.0722 (2)	0.0587 (9)
O5	1.1954 (4)	0.1033 (2)	0.6567 (2)	0.0584 (9)
O6	1.1735 (4)	0.2630 (2)	0.7136 (2)	0.0611 (10)
O7	0.6209 (4)	0.1117 (2)	0.6224 (2)	0.0603 (9)
O8	0.6269 (3)	−0.1255 (2)	0.49791 (19)	0.0452 (7)
O9	0.7096 (3)	−0.22307 (19)	0.6511 (2)	0.0503 (8)
O10	0.2809 (4)	−0.0438 (3)	0.2837 (2)	0.0651 (10)
O11	0.3899 (4)	−0.0374 (3)	0.8873 (3)	0.0746 (11)
O12	0.4032 (4)	−0.2048 (2)	0.8978 (2)	0.0693 (11)
O13	0.7921 (8)	0.1707 (4)	0.7670 (5)	0.155 (3)
H13	0.7511	0.1390	0.7298	0.233*
O14	0.9080 (9)	0.0560 (5)	0.7822 (5)	0.170 (3)
C1	1.0108 (5)	0.1297 (3)	0.5387 (3)	0.0421 (10)
H1	1.0204	0.0730	0.5180	0.051*
C2	1.0959 (5)	0.1561 (3)	0.6102 (3)	0.0431 (11)
C3	1.0854 (5)	0.2418 (3)	0.6400 (3)	0.0459 (12)
C4	0.9863 (5)	0.2978 (3)	0.5990 (3)	0.0435 (11)
H4	0.9778	0.3547	0.6191	0.052*
C5	0.8989 (4)	0.2687 (3)	0.5274 (3)	0.0392 (10)
C6	0.9094 (5)	0.1853 (3)	0.4954 (3)	0.0409 (11)
C7	0.8127 (5)	0.1555 (3)	0.4164 (3)	0.0418 (11)
H7	0.7344	0.1199	0.4399	0.050*
C8	0.7405 (5)	0.2315 (3)	0.3692 (3)	0.0429 (11)
H8	0.6569	0.2103	0.3322	0.051*
C9	0.6873 (5)	0.2966 (3)	0.4343 (3)	0.0485 (12)
H9A	0.6396	0.3443	0.4022	0.058*
H9B	0.6152	0.2693	0.4705	0.058*
C10	0.8949 (5)	0.0982 (3)	0.3538 (3)	0.0465 (12)
C11	0.9482 (5)	0.1421 (3)	0.2749 (3)	0.0395 (10)
C12	0.9214 (5)	0.2304 (3)	0.2613 (3)	0.0373 (10)
C13	0.9852 (5)	0.2728 (3)	0.1928 (3)	0.0418 (10)
C14	1.0712 (5)	0.2259 (3)	0.1371 (3)	0.0481 (12)
C15	1.0980 (6)	0.1383 (3)	0.1470 (3)	0.0579 (14)
H15	1.1563	0.1082	0.1084	0.069*
C16	1.0351 (5)	0.0972 (3)	0.2164 (3)	0.0528 (13)
H16	1.0507	0.0378	0.2247	0.063*
C17	0.9780 (6)	0.3653 (3)	0.1617 (3)	0.0537 (12)
H17A	0.9985	0.4057	0.2102	0.064*
H17B	0.8831	0.3788	0.1335	0.064*
C18	1.1001 (6)	0.3669 (3)	0.0942 (3)	0.0546 (13)
H18	1.1894	0.3908	0.1234	0.065*
C19	1.0670 (6)	0.4164 (3)	0.0102 (3)	0.0560 (13)
C20	0.9266 (7)	0.4032 (5)	−0.0367 (4)	0.093 (2)
H20A	0.9272	0.4310	−0.0937	0.140*
H20B	0.8504	0.4280	−0.0029	0.140*
H20C	0.9093	0.3420	−0.0444	0.140*
C21	1.1675 (8)	0.4707 (5)	−0.0174 (5)	0.098 (2)
H21A	1.1497	0.5027	−0.0691	0.117*
H21B	1.2561	0.4769	0.0150	0.117*
C22	1.1848 (6)	0.0131 (3)	0.6392 (4)	0.0569 (13)
H22A	1.0854	−0.0056	0.6449	0.085*
H22B	1.2477	−0.0181	0.6809	0.085*
H22C	1.2141	0.0016	0.5801	0.085*
C23	1.1554 (7)	0.3471 (4)	0.7485 (4)	0.089 (2)
H23A	1.1807	0.3896	0.7051	0.133*
H23B	1.2179	0.3540	0.8009	0.133*
H23C	1.0551	0.3551	0.7632	0.133*
C24	0.5445 (5)	−0.0350 (3)	0.7596 (3)	0.0460 (12)
H24	0.5372	0.0253	0.7547	0.055*
C25	0.4739 (5)	−0.0772 (3)	0.8255 (3)	0.0504 (12)
C26	0.4799 (5)	−0.1672 (4)	0.8319 (3)	0.0505 (13)
C27	0.5627 (5)	−0.2134 (3)	0.7738 (3)	0.0453 (11)
H27	0.5709	−0.2735	0.7791	0.054*
C28	0.6341 (5)	−0.1696 (3)	0.7072 (3)	0.0393 (11)
C29	0.6271 (5)	−0.0813 (3)	0.6998 (3)	0.0411 (11)
C30	0.7061 (5)	−0.0344 (3)	0.6270 (3)	0.0426 (11)
H30	0.7962	−0.0097	0.6544	0.051*
C31	0.7511 (5)	−0.0987 (3)	0.5562 (3)	0.0451 (11)
H31	0.8256	−0.0717	0.5204	0.054*
C32	0.8122 (5)	−0.1817 (3)	0.5968 (3)	0.0516 (13)
H32A	0.8380	−0.2212	0.5498	0.062*
H32B	0.9007	−0.1685	0.6322	0.062*
C33	0.6176 (5)	0.0400 (3)	0.5878 (3)	0.0465 (12)
C34	0.5262 (5)	0.0206 (3)	0.5075 (3)	0.0416 (11)
C35	0.5385 (5)	−0.0605 (3)	0.4675 (3)	0.0398 (10)
C36	0.4521 (5)	−0.0796 (3)	0.3917 (3)	0.0444 (11)
C37	0.3572 (5)	−0.0167 (3)	0.3587 (3)	0.0517 (13)
C38	0.3425 (6)	0.0647 (4)	0.3960 (4)	0.0626 (15)
H38	0.2774	0.1057	0.3716	0.075*
C39	0.4277 (5)	0.0821 (3)	0.4703 (3)	0.0509 (12)
H39	0.4205	0.1363	0.4972	0.061*
C40	0.4385 (6)	−0.1592 (3)	0.3343 (3)	0.0522 (12)
H40A	0.3892	−0.2060	0.3640	0.063*
H40B	0.5336	−0.1793	0.3168	0.063*
C41	0.3457 (5)	−0.1250 (4)	0.2544 (3)	0.0577 (13)
H41	0.2669	−0.1667	0.2401	0.069*
C42	0.4296 (7)	−0.1102 (5)	0.1741 (4)	0.0754 (17)
C43	0.4633 (10)	−0.0320 (6)	0.1476 (6)	0.131 (3)
H43A	0.4345	0.0164	0.1794	0.157*
H43B	0.5162	−0.0248	0.0968	0.157*
C44	0.4748 (9)	−0.1916 (6)	0.1281 (5)	0.120 (3)
H44A	0.5352	−0.1769	0.0799	0.180*
H44B	0.3891	−0.2220	0.1055	0.180*
H44C	0.5289	−0.2283	0.1695	0.180*
C45	0.3868 (8)	0.0541 (4)	0.8858 (5)	0.095 (2)
H45A	0.4846	0.0762	0.8949	0.142*
H45B	0.3273	0.0749	0.9321	0.142*
H45C	0.3463	0.0736	0.8294	0.142*
C46	0.4079 (8)	−0.2962 (4)	0.9069 (4)	0.091 (2)
H46A	0.3781	−0.3229	0.8514	0.137*
H46B	0.3428	−0.3139	0.9517	0.137*
H46C	0.5060	−0.3140	0.9238	0.137*
C47	0.8792 (10)	0.1287 (5)	0.8118 (7)	0.112 (3)
C48	0.9771 (12)	0.1576 (6)	0.8839 (6)	0.154 (4)
H48A	1.0500	0.1956	0.8612	0.231*
H48B	1.0241	0.1081	0.9117	0.231*
H48C	0.9223	0.1884	0.9268	0.231*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.112 (3)	0.031 (2)	0.060 (2)	−0.001 (2)	−0.006 (2)	0.0034 (16)
O2	0.0536 (18)	0.0438 (19)	0.0396 (17)	0.0054 (16)	0.0061 (15)	0.0061 (14)
O3	0.0485 (18)	0.0437 (18)	0.0497 (19)	0.0102 (16)	0.0000 (15)	0.0052 (15)
O4	0.074 (2)	0.058 (2)	0.0457 (19)	0.0114 (19)	0.0168 (17)	0.0037 (17)
O5	0.066 (2)	0.054 (2)	0.053 (2)	0.0155 (18)	−0.0171 (18)	0.0032 (17)
O6	0.071 (2)	0.057 (2)	0.053 (2)	0.0010 (19)	−0.0170 (18)	−0.0113 (18)
O7	0.076 (2)	0.042 (2)	0.062 (2)	−0.0019 (18)	−0.0040 (19)	−0.0035 (17)
O8	0.0485 (17)	0.0429 (18)	0.0438 (17)	0.0021 (16)	−0.0028 (14)	0.0019 (15)
O9	0.059 (2)	0.0429 (19)	0.0489 (19)	0.0081 (17)	0.0074 (16)	0.0011 (16)
O10	0.065 (2)	0.075 (3)	0.054 (2)	0.014 (2)	−0.0127 (18)	0.0058 (19)
O11	0.095 (3)	0.072 (3)	0.059 (2)	0.009 (2)	0.032 (2)	−0.010 (2)
O12	0.086 (3)	0.071 (3)	0.052 (2)	−0.011 (2)	0.022 (2)	0.0081 (19)
O13	0.190 (6)	0.108 (5)	0.163 (6)	−0.013 (5)	−0.042 (5)	0.020 (5)
O14	0.216 (8)	0.134 (6)	0.159 (6)	0.008 (6)	−0.019 (5)	−0.008 (5)
C1	0.043 (2)	0.039 (2)	0.045 (3)	−0.003 (2)	0.004 (2)	0.000 (2)
C2	0.042 (2)	0.046 (3)	0.040 (3)	0.000 (2)	−0.001 (2)	0.008 (2)
C3	0.044 (3)	0.051 (3)	0.043 (3)	−0.002 (2)	−0.001 (2)	0.000 (2)
C4	0.051 (3)	0.044 (3)	0.036 (2)	0.004 (2)	0.004 (2)	−0.003 (2)
C5	0.035 (2)	0.038 (2)	0.045 (3)	−0.001 (2)	0.005 (2)	0.009 (2)
C6	0.040 (2)	0.040 (3)	0.043 (3)	−0.007 (2)	0.006 (2)	0.012 (2)
C7	0.040 (2)	0.039 (3)	0.046 (3)	−0.009 (2)	−0.003 (2)	0.008 (2)
C8	0.032 (2)	0.053 (3)	0.043 (3)	−0.004 (2)	0.000 (2)	0.008 (2)
C9	0.037 (2)	0.059 (3)	0.049 (3)	0.006 (2)	0.003 (2)	0.009 (2)
C10	0.051 (3)	0.045 (3)	0.043 (3)	−0.006 (2)	−0.010 (2)	−0.001 (2)
C11	0.043 (2)	0.036 (2)	0.039 (2)	0.000 (2)	−0.013 (2)	−0.0058 (19)
C12	0.040 (2)	0.037 (2)	0.034 (2)	0.005 (2)	−0.008 (2)	−0.0041 (19)
C13	0.050 (3)	0.038 (2)	0.037 (2)	0.007 (2)	−0.003 (2)	0.000 (2)
C14	0.056 (3)	0.051 (3)	0.037 (3)	0.008 (2)	−0.003 (2)	−0.002 (2)
C15	0.073 (4)	0.055 (3)	0.045 (3)	0.016 (3)	0.001 (3)	−0.010 (3)
C16	0.073 (3)	0.038 (3)	0.046 (3)	0.007 (3)	−0.010 (3)	−0.003 (2)
C17	0.075 (3)	0.043 (3)	0.043 (3)	0.009 (3)	0.010 (2)	−0.001 (2)
C18	0.071 (3)	0.051 (3)	0.042 (3)	0.001 (3)	0.005 (2)	0.002 (2)
C19	0.072 (3)	0.055 (3)	0.042 (3)	0.008 (3)	0.012 (3)	0.009 (2)
C20	0.105 (5)	0.118 (6)	0.056 (4)	0.005 (5)	−0.014 (4)	0.013 (4)
C21	0.101 (5)	0.118 (6)	0.075 (5)	−0.013 (5)	0.020 (4)	0.040 (4)
C22	0.060 (3)	0.049 (3)	0.061 (3)	0.009 (3)	−0.004 (3)	0.011 (3)
C23	0.107 (5)	0.073 (4)	0.082 (4)	0.017 (4)	−0.037 (4)	−0.030 (3)
C24	0.052 (3)	0.046 (3)	0.040 (3)	0.004 (2)	0.002 (2)	−0.003 (2)
C25	0.053 (3)	0.059 (3)	0.040 (3)	0.002 (3)	0.005 (2)	−0.008 (2)
C26	0.048 (3)	0.069 (4)	0.035 (3)	−0.007 (3)	−0.003 (2)	0.002 (2)
C27	0.048 (3)	0.048 (3)	0.038 (2)	−0.004 (2)	−0.009 (2)	0.003 (2)
C28	0.038 (2)	0.043 (3)	0.036 (2)	0.003 (2)	−0.005 (2)	0.003 (2)
C29	0.036 (2)	0.047 (3)	0.040 (3)	−0.003 (2)	−0.002 (2)	0.002 (2)
C30	0.038 (2)	0.046 (3)	0.044 (3)	−0.006 (2)	0.000 (2)	0.003 (2)
C31	0.038 (2)	0.054 (3)	0.043 (3)	−0.002 (2)	0.005 (2)	0.006 (2)
C32	0.043 (3)	0.065 (3)	0.046 (3)	0.014 (2)	0.000 (2)	0.003 (2)
C33	0.047 (3)	0.044 (3)	0.050 (3)	−0.010 (2)	0.013 (2)	0.004 (2)
C34	0.041 (2)	0.037 (2)	0.047 (3)	−0.002 (2)	0.005 (2)	0.008 (2)
C35	0.039 (2)	0.036 (2)	0.044 (3)	−0.001 (2)	0.011 (2)	0.010 (2)
C36	0.044 (3)	0.050 (3)	0.039 (2)	0.001 (2)	0.002 (2)	0.011 (2)
C37	0.045 (3)	0.056 (3)	0.053 (3)	0.001 (2)	−0.004 (2)	0.014 (3)
C38	0.054 (3)	0.049 (3)	0.084 (4)	0.013 (3)	−0.010 (3)	0.020 (3)
C39	0.052 (3)	0.045 (3)	0.056 (3)	0.003 (2)	0.005 (2)	0.006 (2)
C40	0.058 (3)	0.055 (3)	0.043 (3)	0.009 (3)	0.004 (2)	0.004 (2)
C41	0.055 (3)	0.072 (4)	0.046 (3)	0.002 (3)	−0.006 (2)	0.003 (3)
C42	0.071 (4)	0.095 (5)	0.058 (4)	0.008 (4)	−0.008 (3)	0.009 (4)
C43	0.153 (8)	0.138 (8)	0.107 (7)	0.032 (7)	0.050 (6)	0.058 (6)
C44	0.115 (6)	0.172 (8)	0.073 (5)	−0.009 (6)	0.006 (4)	−0.056 (5)
C45	0.111 (5)	0.092 (5)	0.083 (5)	0.014 (4)	0.035 (4)	−0.036 (4)
C46	0.131 (6)	0.082 (5)	0.062 (4)	−0.030 (4)	0.026 (4)	0.011 (4)
C47	0.114 (6)	0.043 (4)	0.177 (10)	−0.004 (4)	−0.021 (6)	0.035 (5)
C48	0.221 (11)	0.126 (8)	0.109 (7)	−0.052 (8)	−0.059 (8)	0.008 (6)

Geometric parameters (Å, º) top

O1—C10	1.219 (5)	C20—H20B	0.9600
O2—C12	1.355 (5)	C20—H20C	0.9600
O2—C8	1.444 (5)	C21—H21A	0.9300
O3—C5	1.387 (5)	C21—H21B	0.9300
O3—C9	1.426 (5)	C22—H22A	0.9600
O4—C14	1.351 (6)	C22—H22B	0.9600
O4—C18	1.467 (6)	C22—H22C	0.9600
O5—C2	1.384 (5)	C23—H23A	0.9600
O5—C22	1.413 (6)	C23—H23B	0.9600
O6—C3	1.379 (5)	C23—H23C	0.9600
O6—C23	1.407 (6)	C24—C25	1.373 (7)
O7—C33	1.218 (5)	C24—C29	1.398 (6)
O8—C35	1.350 (5)	C24—H24	0.9300
O8—C31	1.461 (5)	C25—C26	1.386 (7)
O9—C28	1.385 (5)	C26—C27	1.380 (7)
O9—C32	1.423 (6)	C27—C28	1.396 (6)
O10—C37	1.366 (6)	C27—H27	0.9300
O10—C41	1.457 (7)	C28—C29	1.362 (6)
O11—C25	1.378 (6)	C29—C30	1.522 (6)
O11—C45	1.405 (7)	C30—C33	1.505 (6)
O12—C26	1.370 (6)	C30—C31	1.526 (6)
O12—C46	1.411 (7)	C30—H30	0.9800
O13—C47	1.207 (8)	C31—C32	1.510 (6)
O13—H13	0.8200	C31—H31	0.9800
O14—C47	1.236 (10)	C32—H32A	0.9700
C1—C2	1.361 (6)	C32—H32B	0.9700
C1—C6	1.400 (6)	C33—C34	1.469 (6)
C1—H1	0.9300	C34—C35	1.391 (6)
C2—C3	1.396 (7)	C34—C39	1.404 (6)
C3—C4	1.375 (6)	C35—C36	1.390 (6)
C4—C5	1.387 (6)	C36—C37	1.376 (6)
C4—H4	0.9300	C36—C40	1.499 (7)
C5—C6	1.373 (6)	C37—C38	1.381 (7)
C6—C7	1.520 (6)	C38—C39	1.361 (7)
C7—C8	1.503 (6)	C38—H38	0.9300
C7—C10	1.516 (7)	C39—H39	0.9300
C7—H7	0.9800	C40—C41	1.533 (6)
C8—C9	1.498 (7)	C40—H40A	0.9700
C8—H8	0.9800	C40—H40B	0.9700
C9—H9A	0.9700	C41—C42	1.481 (8)
C9—H9B	0.9700	C41—H41	0.9800
C10—C11	1.469 (6)	C42—C43	1.307 (10)
C11—C12	1.391 (6)	C42—C44	1.498 (10)
C11—C16	1.396 (6)	C43—H43A	0.9300
C12—C13	1.373 (6)	C43—H43B	0.9300
C13—C14	1.380 (6)	C44—H44A	0.9600
C13—C17	1.496 (7)	C44—H44B	0.9600
C14—C15	1.375 (7)	C44—H44C	0.9600
C15—C16	1.371 (7)	C45—H45A	0.9600
C15—H15	0.9300	C45—H45B	0.9600
C16—H16	0.9300	C45—H45C	0.9600
C17—C18	1.544 (7)	C46—H46A	0.9600
C17—H17A	0.9700	C46—H46B	0.9600
C17—H17B	0.9700	C46—H46C	0.9600
C18—C19	1.497 (7)	C47—C48	1.446 (11)
C18—H18	0.9800	C48—H48A	0.9600
C19—C21	1.322 (8)	C48—H48B	0.9600
C19—C20	1.449 (7)	C48—H48C	0.9600
C20—H20A	0.9600

C12—O2—C8	116.0 (3)	H23B—C23—H23C	109.5
C5—O3—C9	115.2 (3)	C25—C24—C29	120.8 (5)
C14—O4—C18	107.9 (4)	C25—C24—H24	119.6
C2—O5—C22	116.2 (4)	C29—C24—H24	119.6
C3—O6—C23	116.3 (4)	C24—C25—O11	125.1 (5)
C35—O8—C31	115.6 (3)	C24—C25—C26	120.2 (5)
C28—O9—C32	116.5 (3)	O11—C25—C26	114.7 (5)
C37—O10—C41	108.2 (4)	O12—C26—C27	123.9 (5)
C25—O11—C45	116.4 (5)	O12—C26—C25	116.8 (5)
C26—O12—C46	118.4 (5)	C27—C26—C25	119.3 (5)
C47—O13—H13	109.5	C26—C27—C28	119.9 (4)
C2—C1—C6	121.9 (4)	C26—C27—H27	120.1
C2—C1—H1	119.1	C28—C27—H27	120.1
C6—C1—H1	119.1	C29—C28—O9	124.2 (4)
C1—C2—O5	124.4 (4)	C29—C28—C27	121.1 (5)
C1—C2—C3	119.4 (4)	O9—C28—C27	114.6 (4)
O5—C2—C3	116.2 (4)	C28—C29—C24	118.6 (5)
C4—C3—O6	124.2 (4)	C28—C29—C30	120.6 (4)
C4—C3—C2	119.8 (4)	C24—C29—C30	120.8 (4)
O6—C3—C2	115.9 (4)	C33—C30—C29	112.3 (4)
C3—C4—C5	119.5 (4)	C33—C30—C31	111.9 (4)
C3—C4—H4	120.2	C29—C30—C31	110.5 (4)
C5—C4—H4	120.2	C33—C30—H30	107.3
C6—C5—O3	123.4 (4)	C29—C30—H30	107.3
C6—C5—C4	121.8 (4)	C31—C30—H30	107.3
O3—C5—C4	114.8 (4)	O8—C31—C32	105.5 (4)
C5—C6—C1	117.5 (4)	O8—C31—C30	112.1 (3)
C5—C6—C7	120.6 (4)	C32—C31—C30	111.7 (4)
C1—C6—C7	121.9 (4)	O8—C31—H31	109.1
C8—C7—C10	112.0 (4)	C32—C31—H31	109.1
C8—C7—C6	111.3 (4)	C30—C31—H31	109.1
C10—C7—C6	112.1 (4)	O9—C32—C31	111.7 (4)
C8—C7—H7	107.0	O9—C32—H32A	109.3
C10—C7—H7	107.0	C31—C32—H32A	109.3
C6—C7—H7	107.0	O9—C32—H32B	109.3
O2—C8—C9	105.4 (4)	C31—C32—H32B	109.3
O2—C8—C7	113.3 (3)	H32A—C32—H32B	107.9
C9—C8—C7	110.9 (4)	O7—C33—C34	122.6 (4)
O2—C8—H8	109.1	O7—C33—C30	121.0 (4)
C9—C8—H8	109.1	C34—C33—C30	116.3 (4)
C7—C8—H8	109.1	C35—C34—C39	119.5 (4)
O3—C9—C8	112.3 (3)	C35—C34—C33	119.1 (4)
O3—C9—H9A	109.1	C39—C34—C33	121.5 (4)
C8—C9—H9A	109.1	O8—C35—C36	115.6 (4)
O3—C9—H9B	109.1	O8—C35—C34	125.0 (4)
C8—C9—H9B	109.1	C36—C35—C34	119.4 (4)
H9A—C9—H9B	107.9	C37—C36—C35	118.3 (5)
O1—C10—C11	123.6 (5)	C37—C36—C40	109.2 (4)
O1—C10—C7	120.9 (4)	C35—C36—C40	132.5 (4)
C11—C10—C7	115.5 (4)	O10—C37—C36	112.0 (4)
C12—C11—C16	119.3 (4)	O10—C37—C38	123.9 (5)
C12—C11—C10	120.2 (4)	C36—C37—C38	124.1 (5)
C16—C11—C10	120.3 (4)	C39—C38—C37	116.7 (5)
O2—C12—C13	116.8 (4)	C39—C38—H38	121.6
O2—C12—C11	123.4 (4)	C37—C38—H38	121.6
C13—C12—C11	119.7 (4)	C38—C39—C34	122.0 (5)
C12—C13—C14	118.9 (4)	C38—C39—H39	119.0
C12—C13—C17	132.3 (4)	C34—C39—H39	119.0
C14—C13—C17	108.8 (4)	C36—C40—C41	101.7 (4)
O4—C14—C15	124.0 (5)	C36—C40—H40A	111.4
O4—C14—C13	112.8 (4)	C41—C40—H40A	111.4
C15—C14—C13	123.2 (5)	C36—C40—H40B	111.4
C16—C15—C14	117.1 (5)	C41—C40—H40B	111.4
C16—C15—H15	121.5	H40A—C40—H40B	109.3
C14—C15—H15	121.5	O10—C41—C42	110.4 (5)
C15—C16—C11	121.7 (5)	O10—C41—C40	105.8 (4)
C15—C16—H16	119.1	C42—C41—C40	114.0 (4)
C11—C16—H16	119.1	O10—C41—H41	108.8
C13—C17—C18	101.5 (4)	C42—C41—H41	108.8
C13—C17—H17A	111.5	C40—C41—H41	108.8
C18—C17—H17A	111.5	C43—C42—C41	122.0 (7)
C13—C17—H17B	111.5	C43—C42—C44	123.5 (7)
C18—C17—H17B	111.5	C41—C42—C44	114.5 (6)
H17A—C17—H17B	109.3	C42—C43—H43A	120.0
O4—C18—C19	108.9 (4)	C42—C43—H43B	120.0
O4—C18—C17	105.1 (4)	H43A—C43—H43B	120.0
C19—C18—C17	116.3 (4)	C42—C44—H44A	109.5
O4—C18—H18	108.8	C42—C44—H44B	109.5
C19—C18—H18	108.8	H44A—C44—H44B	109.5
C17—C18—H18	108.8	C42—C44—H44C	109.5
C21—C19—C20	123.2 (6)	H44A—C44—H44C	109.5
C21—C19—C18	118.1 (5)	H44B—C44—H44C	109.5
C20—C19—C18	118.8 (5)	O11—C45—H45A	109.5
C19—C20—H20A	109.5	O11—C45—H45B	109.5
C19—C20—H20B	109.5	H45A—C45—H45B	109.5
H20A—C20—H20B	109.5	O11—C45—H45C	109.5
C19—C20—H20C	109.5	H45A—C45—H45C	109.5
H20A—C20—H20C	109.5	H45B—C45—H45C	109.5
H20B—C20—H20C	109.5	O12—C46—H46A	109.5
C19—C21—H21A	120.0	O12—C46—H46B	109.5
C19—C21—H21B	120.0	H46A—C46—H46B	109.5
H21A—C21—H21B	120.0	O12—C46—H46C	109.5
O5—C22—H22A	109.5	H46A—C46—H46C	109.5
O5—C22—H22B	109.5	H46B—C46—H46C	109.5
H22A—C22—H22B	109.5	O13—C47—O14	115.2 (10)
O5—C22—H22C	109.5	O13—C47—C48	128.7 (9)
H22A—C22—H22C	109.5	O14—C47—C48	114.5 (9)
H22B—C22—H22C	109.5	C47—C48—H48A	109.5
O6—C23—H23A	109.5	C47—C48—H48B	109.5
O6—C23—H23B	109.5	H48A—C48—H48B	109.5
H23A—C23—H23B	109.5	C47—C48—H48C	109.5
O6—C23—H23C	109.5	H48A—C48—H48C	109.5
H23A—C23—H23C	109.5	H48B—C48—H48C	109.5

O3—C5—C6—C7	−0.6 (6)	C32—O9—C28—C29	15.2 (6)
C5—C6—C7—C8	13.9 (6)	O8—C30—C31—C33	50.1 (5)
C6—C7—C8—C9	−41.7 (5)	C30—C31—C33—C34	−152.5 (5)
C7—C8—C9—O3	59.9 (5)	C31—C33—C34—C35	9.9 (4)
C8—C9—O3—C5	−46.6 (5)	C33—C34—C35—O8	1.7 (6)
C9—O3—C5—C6	17.1 (6)	C34—C35—O8—C30	2.1 (4)
O2—C8—C7—C10	−49.9 (5)	C35—O8—C30—C31	−139.4 (4)
C8—C7—C10—C11	27.0 (5)	O4—C13—C14—C17	−0.9 (6)
C7—C10—C11—C12	−0.4 (6)	C13—C14—C17—C18	167.0 (5)
C10—C11—C12—O2	−4.9 (6)	C14—C7—C18—O4	0.9 (2)
C11—C12—O2—C8	−18.7 (5)	C7—C18—O4—C13	5.85 (13)
C12—O2—C8—C7	46.5 (5)	C18—O4—C13—C14	−168.3 (5)
O9—C28—C29—C30	−0.6 (7)	O10—C36—C37—C40	1.0 (6)
C28—C29—C30—C31	15.1 (6)	C36—C37—C38—C39	−0.4 (8)
C29—C30—C31—C32	−42.4 (5)	C37—C38—C39—O10	0.6 (4)
C30—C31—C32—O9	58.0 (5)	C38—C39—O10—C36	−179.4 (8)
C31—C32—O9—C28	−43.5 (5)	C39—O10—C36—C37	0.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O7	0.82	2.01	2.776 (7)	155

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