Maleopimaric anhydride ethyl ester

Li, Y.-H.; Ren, T.-R.; Guo, J.-P.; Liu, J.-C.

doi:10.1107/S1600536805038390

Maleopimaric anhydride ethyl ester

Y.-H. Li, T.-R. Ren, J.-P. Guo and J.-C. Liu

The title compound, C₂₆H₃₆O₅, is a derivative of abietic acid formed by an endo-Diels-Alder reaction between maleic anhydride and the diene levopimaric acid ethyl ester. The two fused and unbridged cyclohexane rings have chair conformations and the anhydride ring is planar.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038390/sj6161sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038390/sj6161Isup2.hkl Contains datablock I

CCDC reference: 294137

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.070
wR factor = 0.156
Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.767     0.984
            Tmin(prime) and Tmax expected:      0.967     0.984
            RR(prime) =      0.793
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.79
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.79 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.48 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C24
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H22A   ..  H23B    ..       1.82 Ang.

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           25.00
           From the CIF: _reflns_number_total               2354
           Count of symmetry unique reflns         2354
           Completeness (_total/calc)            100.00%
           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
  10 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 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
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1999); software used to prepare material for publication: SHELXL97.

Maleopimaric anhydride ethyl ester top

Crystal data top

C₂₆H₃₆O₅	D_x = 1.218 Mg m⁻³
M_r = 428.55	Melting point = 159–161 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3834 reflections
a = 9.2973 (6) Å	θ = 2.4–27.6°
b = 13.2060 (9) Å	µ = 0.08 mm⁻¹
c = 19.0372 (13) Å	T = 293 K
V = 2337.4 (3) Å³	Block, colorless
Z = 4	0.40 × 0.30 × 0.20 mm
F(000) = 928

Data collection top

Bruker SMART CCD diffractometer	2354 independent reflections
Radiation source: fine-focus sealed tube	2292 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
T_min = 0.767, T_max = 0.984	k = −15→6
9763 measured reflections	l = −22→21

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)] = 0.070	H-atom parameters constrained
wR(F²) = 0.156	w = 1/[σ²(F_o²) + (0.0503P)² + 1.3297P] where P = (F_o² + 2F_c²)/3
S = 1.28	(Δ/σ)_max < 0.001
2354 reflections	Δρ_max = 0.19 e Å⁻³
280 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Absolute structure: see text
Primary atom site location: structure-invariant direct methods

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	0.3129 (5)	0.1995 (3)	0.1708 (2)	0.0461 (11)
H1A	0.3589	0.1332	0.1651	0.055*
C2	0.3093 (5)	0.2555 (4)	0.1005 (2)	0.0449 (11)
H2A	0.3633	0.2169	0.0653	0.054*
C3	0.1528 (6)	0.2577 (4)	0.0808 (3)	0.0495 (12)
C4	0.1568 (6)	0.1862 (4)	0.1899 (3)	0.0541 (13)
C5	0.3940 (5)	0.2622 (3)	0.2255 (2)	0.0446 (11)
H5A	0.3978	0.2269	0.2708	0.053*
C6	0.5447 (5)	0.2804 (4)	0.1965 (2)	0.0454 (11)
H6A	0.5919	0.2158	0.1888	0.054*
H6B	0.6007	0.3181	0.2306	0.054*
C7	0.5399 (5)	0.3397 (3)	0.1270 (2)	0.0396 (10)
H7A	0.5741	0.2931	0.0905	0.048*
C8	0.3777 (5)	0.3633 (3)	0.1091 (2)	0.0378 (10)
C9	0.3085 (5)	0.4117 (3)	0.1713 (2)	0.0381 (10)
H9A	0.2615	0.4736	0.1676	0.046*
C10	0.3166 (5)	0.3631 (3)	0.2323 (2)	0.0391 (10)
C11	0.6409 (5)	0.4334 (3)	0.1244 (2)	0.0406 (10)
C12	0.6214 (5)	0.4801 (3)	0.0501 (2)	0.0428 (11)
H12A	0.6354	0.4233	0.0177	0.051*
C13	0.4668 (5)	0.5135 (4)	0.0385 (2)	0.0478 (12)
H13A	0.4588	0.5465	−0.0069	0.057*
H13B	0.4400	0.5621	0.0743	0.057*
C14	0.3648 (5)	0.4236 (4)	0.0412 (2)	0.0465 (11)
H14A	0.3848	0.3792	0.0018	0.056*
H14B	0.2668	0.4477	0.0363	0.056*
C15	0.7967 (5)	0.3952 (4)	0.1306 (3)	0.0497 (12)
H15A	0.8127	0.3713	0.1781	0.060*
H15B	0.8094	0.3381	0.0992	0.060*
C16	0.9086 (5)	0.4748 (4)	0.1133 (3)	0.0570 (14)
H16A	1.0039	0.4454	0.1172	0.068*
H16B	0.9017	0.5300	0.1468	0.068*
C17	0.8867 (5)	0.5155 (4)	0.0392 (3)	0.0589 (14)
H17A	0.9023	0.4611	0.0058	0.071*
H17B	0.9579	0.5676	0.0301	0.071*
C18	0.7354 (6)	0.5602 (4)	0.0275 (2)	0.0515 (12)
C19	0.2601 (6)	0.3963 (4)	0.3030 (3)	0.0513 (12)
H19A	0.2025	0.3404	0.3218	0.062*
C20	0.1630 (7)	0.4880 (5)	0.2989 (3)	0.0792 (18)
H20A	0.0852	0.4745	0.2671	0.119*
H20B	0.2171	0.5451	0.2824	0.119*
H20C	0.1250	0.5025	0.3447	0.119*
C21	0.3833 (7)	0.4148 (6)	0.3544 (3)	0.0823 (19)
H21A	0.4429	0.3556	0.3568	0.123*
H21B	0.3447	0.4292	0.4001	0.123*
H21C	0.4396	0.4714	0.3387	0.123*
C22	0.6122 (5)	0.5084 (4)	0.1848 (2)	0.0464 (11)
H22A	0.6768	0.5648	0.1810	0.070*
H22B	0.6270	0.4749	0.2290	0.070*
H22C	0.5147	0.5321	0.1821	0.070*
C23	0.7228 (7)	0.6635 (4)	0.0642 (3)	0.0638 (15)
H23A	0.7977	0.7075	0.0476	0.096*
H23B	0.7322	0.6546	0.1140	0.096*
H23C	0.6309	0.6929	0.0538	0.096*
C24	0.7173 (6)	0.5702 (4)	−0.0517 (3)	0.0537 (13)
C25	0.6706 (9)	0.6826 (5)	−0.1462 (3)	0.088 (2)
H25A	0.5737	0.6634	−0.1596	0.106*
H25B	0.7379	0.6430	−0.1738	0.106*
C26	0.6927 (11)	0.7894 (5)	−0.1589 (4)	0.106 (3)
H26A	0.6816	0.8032	−0.2082	0.160*
H26B	0.7878	0.8081	−0.1443	0.160*
H26C	0.6232	0.8278	−0.1328	0.160*
O1	0.0709 (4)	0.2190 (3)	0.13563 (19)	0.0581 (9)
O2	0.0956 (4)	0.2867 (3)	0.02942 (18)	0.0640 (10)
O3	0.1054 (4)	0.1569 (3)	0.2429 (2)	0.0781 (12)
O4	0.6928 (6)	0.6641 (3)	−0.07238 (18)	0.0772 (13)
O5	0.7222 (6)	0.5018 (3)	−0.09284 (18)	0.0822 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.047 (3)	0.029 (2)	0.062 (3)	0.005 (2)	0.000 (2)	−0.001 (2)
C2	0.042 (3)	0.046 (3)	0.047 (2)	0.005 (2)	−0.002 (2)	−0.017 (2)
C3	0.053 (3)	0.042 (3)	0.054 (3)	0.000 (2)	−0.005 (3)	−0.016 (2)
C4	0.051 (3)	0.045 (3)	0.067 (3)	−0.006 (2)	−0.010 (3)	0.002 (3)
C5	0.045 (3)	0.040 (2)	0.049 (2)	0.005 (2)	−0.003 (2)	0.003 (2)
C6	0.042 (3)	0.039 (2)	0.055 (3)	0.004 (2)	−0.009 (2)	−0.001 (2)
C7	0.043 (2)	0.037 (2)	0.039 (2)	0.006 (2)	−0.003 (2)	−0.006 (2)
C8	0.036 (2)	0.037 (2)	0.041 (2)	0.001 (2)	−0.0038 (19)	−0.0047 (19)
C9	0.037 (2)	0.033 (2)	0.044 (2)	0.003 (2)	−0.0056 (19)	−0.005 (2)
C10	0.036 (2)	0.039 (2)	0.042 (2)	−0.006 (2)	−0.0053 (19)	−0.003 (2)
C11	0.039 (2)	0.043 (2)	0.039 (2)	0.001 (2)	0.0015 (19)	−0.003 (2)
C12	0.052 (3)	0.039 (2)	0.038 (2)	0.000 (2)	0.005 (2)	−0.010 (2)
C13	0.062 (3)	0.044 (3)	0.036 (2)	0.015 (3)	0.006 (2)	0.003 (2)
C14	0.041 (3)	0.054 (3)	0.045 (2)	0.002 (2)	−0.003 (2)	−0.003 (2)
C15	0.046 (3)	0.052 (3)	0.051 (3)	−0.004 (2)	−0.002 (2)	−0.010 (2)
C16	0.038 (3)	0.067 (3)	0.066 (3)	0.000 (3)	0.000 (2)	−0.012 (3)
C17	0.051 (3)	0.060 (3)	0.066 (3)	−0.015 (3)	0.016 (3)	−0.012 (3)
C18	0.067 (3)	0.045 (3)	0.042 (2)	−0.006 (3)	0.011 (2)	−0.009 (2)
C19	0.059 (3)	0.042 (3)	0.052 (3)	−0.005 (2)	0.004 (2)	0.009 (2)
C20	0.102 (5)	0.077 (4)	0.059 (3)	0.022 (4)	0.021 (3)	0.000 (3)
C21	0.095 (5)	0.100 (5)	0.052 (3)	−0.018 (4)	−0.004 (3)	−0.009 (3)
C22	0.052 (3)	0.046 (3)	0.041 (2)	−0.006 (2)	0.002 (2)	−0.006 (2)
C23	0.083 (4)	0.051 (3)	0.057 (3)	−0.009 (3)	0.007 (3)	−0.008 (3)
C24	0.060 (3)	0.046 (3)	0.055 (3)	−0.010 (3)	0.014 (3)	−0.009 (2)
C25	0.113 (6)	0.091 (5)	0.061 (4)	−0.022 (5)	0.003 (4)	0.018 (3)
C26	0.152 (8)	0.084 (5)	0.083 (5)	0.013 (6)	0.000 (5)	0.021 (4)
O1	0.0427 (18)	0.063 (2)	0.068 (2)	−0.0062 (18)	−0.0064 (17)	−0.0017 (19)
O2	0.059 (2)	0.076 (2)	0.057 (2)	−0.001 (2)	−0.0202 (18)	−0.011 (2)
O3	0.061 (2)	0.091 (3)	0.082 (3)	−0.018 (2)	0.002 (2)	0.031 (2)
O4	0.129 (4)	0.053 (2)	0.049 (2)	−0.007 (3)	0.007 (2)	0.0002 (17)
O5	0.132 (4)	0.068 (2)	0.0458 (19)	0.005 (3)	0.010 (2)	−0.011 (2)

Geometric parameters (Å, º) top

C1—C4	1.506 (7)	C15—C16	1.514 (7)
C1—C2	1.529 (6)	C15—H15A	0.9700
C1—C5	1.530 (6)	C15—H15B	0.9700
C1—H1A	0.9800	C16—C17	1.524 (7)
C2—C3	1.503 (7)	C16—H16A	0.9700
C2—C8	1.568 (6)	C16—H16B	0.9700
C2—H2A	0.9800	C17—C18	1.542 (8)
C3—O2	1.178 (6)	C17—H17A	0.9700
C3—O1	1.389 (6)	C17—H17B	0.9700
C4—O3	1.181 (6)	C18—C24	1.523 (7)
C4—O1	1.376 (6)	C18—C23	1.537 (7)
C5—C10	1.519 (6)	C19—C20	1.511 (7)
C5—C6	1.526 (6)	C19—C21	1.527 (7)
C5—H5A	0.9800	C19—H19A	0.9800
C6—C7	1.538 (6)	C20—H20A	0.9600
C6—H6A	0.9700	C20—H20B	0.9600
C6—H6B	0.9700	C20—H20C	0.9600
C7—C11	1.555 (6)	C21—H21A	0.9600
C7—C8	1.577 (6)	C21—H21B	0.9600
C7—H7A	0.9800	C21—H21C	0.9600
C8—C9	1.492 (6)	C22—H22A	0.9600
C8—C14	1.524 (6)	C22—H22B	0.9600
C9—C10	1.329 (6)	C22—H22C	0.9600
C9—H9A	0.9300	C23—H23A	0.9600
C10—C19	1.509 (6)	C23—H23B	0.9600
C11—C15	1.538 (6)	C23—H23C	0.9600
C11—C22	1.540 (6)	C24—O5	1.196 (6)
C11—C12	1.554 (6)	C24—O4	1.321 (6)
C12—C13	1.519 (7)	C25—O4	1.442 (6)
C12—C18	1.557 (7)	C25—C26	1.445 (9)
C12—H12A	0.9800	C25—H25A	0.9700
C13—C14	1.520 (7)	C25—H25B	0.9700
C13—H13A	0.9700	C26—H26A	0.9600
C13—H13B	0.9700	C26—H26B	0.9600
C14—H14A	0.9700	C26—H26C	0.9600
C14—H14B	0.9700

C4—C1—C2	104.2 (4)	C16—C15—C11	113.7 (4)
C4—C1—C5	111.9 (4)	C16—C15—H15A	108.8
C2—C1—C5	110.2 (4)	C11—C15—H15A	108.8
C4—C1—H1A	110.1	C16—C15—H15B	108.8
C2—C1—H1A	110.1	C11—C15—H15B	108.8
C5—C1—H1A	110.1	H15A—C15—H15B	107.7
C3—C2—C1	104.4 (4)	C15—C16—C17	110.7 (4)
C3—C2—C8	113.7 (4)	C15—C16—H16A	109.5
C1—C2—C8	109.8 (3)	C17—C16—H16A	109.5
C3—C2—H2A	109.6	C15—C16—H16B	109.5
C1—C2—H2A	109.6	C17—C16—H16B	109.5
C8—C2—H2A	109.6	H16A—C16—H16B	108.1
O2—C3—O1	119.7 (5)	C16—C17—C18	113.0 (4)
O2—C3—C2	130.6 (5)	C16—C17—H17A	109.0
O1—C3—C2	109.6 (4)	C18—C17—H17A	109.0
O3—C4—O1	120.7 (5)	C16—C17—H17B	109.0
O3—C4—C1	129.3 (5)	C18—C17—H17B	109.0
O1—C4—C1	110.0 (4)	H17A—C17—H17B	107.8
C10—C5—C6	109.1 (4)	C24—C18—C23	111.4 (4)
C10—C5—C1	107.4 (4)	C24—C18—C17	106.0 (4)
C6—C5—C1	106.9 (4)	C23—C18—C17	110.1 (5)
C10—C5—H5A	111.1	C24—C18—C12	104.9 (4)
C6—C5—H5A	111.1	C23—C18—C12	115.2 (4)
C1—C5—H5A	111.1	C17—C18—C12	108.8 (4)
C5—C6—C7	111.4 (4)	C10—C19—C20	113.3 (4)
C5—C6—H6A	109.3	C10—C19—C21	110.9 (4)
C7—C6—H6A	109.3	C20—C19—C21	110.6 (5)
C5—C6—H6B	109.3	C10—C19—H19A	107.2
C7—C6—H6B	109.3	C20—C19—H19A	107.2
H6A—C6—H6B	108.0	C21—C19—H19A	107.2
C6—C7—C11	114.5 (4)	C19—C20—H20A	109.5
C6—C7—C8	108.3 (4)	C19—C20—H20B	109.5
C11—C7—C8	114.4 (4)	H20A—C20—H20B	109.5
C6—C7—H7A	106.3	C19—C20—H20C	109.5
C11—C7—H7A	106.3	H20A—C20—H20C	109.5
C8—C7—H7A	106.3	H20B—C20—H20C	109.5
C9—C8—C14	114.6 (4)	C19—C21—H21A	109.5
C9—C8—C2	107.3 (4)	C19—C21—H21B	109.5
C14—C8—C2	110.7 (3)	H21A—C21—H21B	109.5
C9—C8—C7	109.0 (3)	C19—C21—H21C	109.5
C14—C8—C7	111.2 (4)	H21A—C21—H21C	109.5
C2—C8—C7	103.3 (3)	H21B—C21—H21C	109.5
C10—C9—C8	117.5 (4)	C11—C22—H22A	109.5
C10—C9—H9A	121.2	C11—C22—H22B	109.5
C8—C9—H9A	121.2	H22A—C22—H22B	109.5
C9—C10—C19	128.2 (4)	C11—C22—H22C	109.5
C9—C10—C5	112.1 (4)	H22A—C22—H22C	109.5
C19—C10—C5	119.7 (4)	H22B—C22—H22C	109.5
C15—C11—C22	108.5 (4)	C18—C23—H23A	109.5
C15—C11—C12	108.0 (4)	C18—C23—H23B	109.5
C22—C11—C12	113.9 (4)	H23A—C23—H23B	109.5
C15—C11—C7	107.8 (4)	C18—C23—H23C	109.5
C22—C11—C7	112.5 (4)	H23A—C23—H23C	109.5
C12—C11—C7	105.9 (3)	H23B—C23—H23C	109.5
C13—C12—C11	111.0 (4)	O5—C24—O4	121.3 (5)
C13—C12—C18	114.0 (4)	O5—C24—C18	125.4 (5)
C11—C12—C18	116.2 (4)	O4—C24—C18	113.3 (4)
C13—C12—H12A	104.8	O4—C25—C26	108.0 (6)
C11—C12—H12A	104.8	O4—C25—H25A	110.1
C18—C12—H12A	104.8	C26—C25—H25A	110.1
C12—C13—C14	111.0 (4)	O4—C25—H25B	110.1
C12—C13—H13A	109.4	C26—C25—H25B	110.1
C14—C13—H13A	109.4	H25A—C25—H25B	108.4
C12—C13—H13B	109.4	C25—C26—H26A	109.5
C14—C13—H13B	109.4	C25—C26—H26B	109.5
H13A—C13—H13B	108.0	H26A—C26—H26B	109.5
C13—C14—C8	112.8 (4)	C25—C26—H26C	109.5
C13—C14—H14A	109.0	H26A—C26—H26C	109.5
C8—C14—H14A	109.0	H26B—C26—H26C	109.5
C13—C14—H14B	109.0	C4—O1—C3	111.2 (4)
C8—C14—H14B	109.0	C24—O4—C25	118.3 (5)
H14A—C14—H14B	107.8

C4—C1—C2—C3	−7.1 (5)	C6—C7—C11—C12	178.9 (4)
C5—C1—C2—C3	−127.3 (4)	C8—C7—C11—C12	−55.2 (4)
C4—C1—C2—C8	115.2 (4)	C15—C11—C12—C13	176.3 (4)
C5—C1—C2—C8	−5.0 (5)	C22—C11—C12—C13	−63.1 (5)
C1—C2—C3—O2	−174.8 (5)	C7—C11—C12—C13	61.1 (4)
C8—C2—C3—O2	65.5 (7)	C15—C11—C12—C18	−51.3 (5)
C1—C2—C3—O1	6.3 (5)	C22—C11—C12—C18	69.2 (5)
C8—C2—C3—O1	−113.4 (4)	C7—C11—C12—C18	−166.6 (4)
C2—C1—C4—O3	−171.1 (6)	C11—C12—C13—C14	−63.0 (5)
C5—C1—C4—O3	−52.0 (8)	C18—C12—C13—C14	163.6 (4)
C2—C1—C4—O1	5.9 (5)	C12—C13—C14—C8	55.4 (5)
C5—C1—C4—O1	124.9 (4)	C9—C8—C14—C13	76.2 (5)
C4—C1—C5—C10	−56.7 (5)	C2—C8—C14—C13	−162.3 (4)
C2—C1—C5—C10	58.8 (5)	C7—C8—C14—C13	−48.0 (5)
C4—C1—C5—C6	−173.7 (4)	C22—C11—C15—C16	−70.3 (5)
C2—C1—C5—C6	−58.2 (5)	C12—C11—C15—C16	53.6 (5)
C10—C5—C6—C7	−54.9 (5)	C7—C11—C15—C16	167.6 (4)
C1—C5—C6—C7	61.0 (5)	C11—C15—C16—C17	−58.0 (5)
C5—C6—C7—C11	129.6 (4)	C15—C16—C17—C18	57.1 (6)
C5—C6—C7—C8	0.7 (5)	C16—C17—C18—C24	−164.9 (4)
C3—C2—C8—C9	66.7 (5)	C16—C17—C18—C23	74.5 (5)
C1—C2—C8—C9	−49.9 (4)	C16—C17—C18—C12	−52.6 (5)
C3—C2—C8—C14	−59.0 (5)	C13—C12—C18—C24	−64.6 (5)
C1—C2—C8—C14	−175.6 (4)	C11—C12—C18—C24	164.4 (4)
C3—C2—C8—C7	−178.2 (4)	C13—C12—C18—C23	58.2 (6)
C1—C2—C8—C7	65.2 (4)	C11—C12—C18—C23	−72.8 (6)
C6—C7—C8—C9	51.8 (5)	C13—C12—C18—C17	−177.7 (4)
C11—C7—C8—C9	−77.2 (4)	C11—C12—C18—C17	51.3 (5)
C6—C7—C8—C14	179.1 (4)	C9—C10—C19—C20	10.6 (7)
C11—C7—C8—C14	50.1 (5)	C5—C10—C19—C20	−169.4 (4)
C6—C7—C8—C2	−62.0 (4)	C9—C10—C19—C21	−114.6 (6)
C11—C7—C8—C2	168.9 (3)	C5—C10—C19—C21	65.4 (6)
C14—C8—C9—C10	−179.7 (4)	C23—C18—C24—O5	180.0 (6)
C2—C8—C9—C10	56.9 (5)	C17—C18—C24—O5	60.3 (7)
C7—C8—C9—C10	−54.3 (5)	C12—C18—C24—O5	−54.7 (7)
C8—C9—C10—C19	178.1 (4)	C23—C18—C24—O4	−0.9 (7)
C8—C9—C10—C5	−1.9 (6)	C17—C18—C24—O4	−120.6 (5)
C6—C5—C10—C9	58.0 (5)	C12—C18—C24—O4	124.4 (5)
C1—C5—C10—C9	−57.6 (5)	O3—C4—O1—C3	175.2 (5)
C6—C5—C10—C19	−122.0 (4)	C1—C4—O1—C3	−2.1 (6)
C1—C5—C10—C19	122.4 (4)	O2—C3—O1—C4	178.1 (4)
C6—C7—C11—C15	63.5 (5)	C2—C3—O1—C4	−2.8 (5)
C8—C7—C11—C15	−170.6 (4)	O5—C24—O4—C25	0.5 (9)
C6—C7—C11—C22	−56.0 (5)	C18—C24—O4—C25	−178.6 (5)
C8—C7—C11—C22	69.8 (5)	C26—C25—O4—C24	−161.7 (7)

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