Azadirone

Malathi, R.; Rajan, S.S.; Krishnan, M.S.; Gopalakrishnan, G.; Suresh, G.

doi:10.1107/S1600536806048410

Azadirone

R. Malathi, S. S. Rajan, M. S. Krishnan, G. Gopalakrishnan and G. Suresh

The title compound [systematic name: (5α,7α,13α,17α)-7-(acetyloxy)-21,23-epoxy-4,4,8-trimethyl-24-norchola-1,14,20,22-tetraen-3-one], C₂₈H₃₆O₄, was isolated from uncrushed green leaves of Azadirachta indica A. Juss (neem) and has been reported to possess antifeedant activity against Spodoptera litura similar to nimonol extracted from neem leaves. Conformational differences from nimonol are seen in the orientation of the functional groups such as the acetoxy and furan rings. Weak intermolecular C—H

O hydrogen bonds help stabilize the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048410/lh2208sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048410/lh2208Isup2.hkl Contains datablock I

CCDC reference: 630047

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.043
wR factor = 0.127
Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C12
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C26
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11A   ..  O3      ..       2.66 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H27A   ..  O21     ..       2.76 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           72.13
           From the CIF: _reflns_number_total               2387
           Count of symmetry unique reflns         2394
           Completeness (_total/calc)             99.71%
           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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17    = .          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
  10 ALERT level G = General alerts; check

   9 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
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PARST97 (Nardelli, 1995)'.

(5α,7α,13α,17α)-7-(acetyloxy)-21,23-epoxy-4,4,8-trimethyl-24- norchola-1,14,20,22-tetraen-3-one top

Crystal data top

C₂₈H₃₆O₄	D_x = 1.193 Mg m⁻³
M_r = 436.57	Cu Kα radiation, λ = 1.54178 Å
Trigonal, P3₁	Cell parameters from 23 reflections
Hall symbol: P 31	θ = 15–30°
a = 10.818 (3) Å	µ = 0.62 mm⁻¹
c = 17.984 (5) Å	T = 293 K
V = 1822.7 (10) Å³	Rod, colourless
Z = 3	0.39 × 0.28 × 0.15 mm
F(000) = 708

Data collection top

Enraf–Nonius CAD-4 diffractometer	1996 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.080
Graphite monochromator	θ_max = 72.1°, θ_min = 4.7°
non–profiled ω/2θ scans	h = −13→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→13
T_min = 0.852, T_max = 0.909	l = −22→22
7386 measured reflections	3 standard reflections every 200 reflections
2387 independent reflections	intensity decay: 2%

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0689P)² + 0.0034P] where P = (F_o² + 2F_c²)/3
2387 reflections	(Δ/σ)_max = 0.001
290 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.14 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
O3	0.2355 (3)	−0.3346 (3)	0.08371 (15)	0.0917 (8)
O7	0.2563 (2)	0.1286 (2)	0.28301 (11)	0.0614 (5)
O21	0.2044 (4)	0.0794 (4)	0.72069 (15)	0.1049 (10)
O31	0.2492 (4)	0.3010 (4)	0.2186 (2)	0.1126 (11)
C1	0.3759 (4)	−0.2205 (4)	0.26525 (17)	0.0709 (8)
H1	0.3802	−0.2628	0.3094	0.085*
C2	0.3027 (4)	−0.3070 (4)	0.20751 (19)	0.0743 (8)
H2	0.2566	−0.4053	0.2144	0.089*
C3	0.2935 (4)	−0.2515 (4)	0.13518 (17)	0.0719 (8)
C4	0.3594 (4)	−0.0910 (4)	0.12435 (15)	0.0698 (8)
C5	0.3772 (4)	−0.0184 (3)	0.20120 (14)	0.0604 (7)
H5	0.2791	−0.0571	0.2192	0.072*
C6	0.4362 (4)	0.1422 (3)	0.19916 (15)	0.0629 (7)
H6A	0.5380	0.1903	0.1894	0.076*
H6B	0.3912	0.1652	0.1590	0.076*
C7	0.4097 (3)	0.1959 (3)	0.27242 (14)	0.0574 (6)
H7	0.4512	0.2997	0.2700	0.069*
C8	0.4730 (3)	0.1573 (3)	0.33952 (15)	0.0585 (6)
C9	0.4238 (3)	−0.0046 (3)	0.33746 (15)	0.0578 (6)
H9	0.3198	−0.0537	0.3430	0.069*
C10	0.4502 (4)	−0.0611 (4)	0.26213 (15)	0.0621 (7)
C11	0.4781 (5)	−0.0471 (4)	0.40700 (17)	0.0738 (9)
H11A	0.4398	−0.1495	0.4062	0.089*
H11B	0.5812	−0.0019	0.4042	0.089*
C12	0.4396 (5)	−0.0080 (5)	0.47832 (18)	0.0869 (12)
H12A	0.5262	0.0432	0.5076	0.104*
H12B	0.3771	−0.0956	0.5048	0.104*
C13	0.3677 (3)	0.0816 (3)	0.47635 (14)	0.0544 (6)
C14	0.4235 (4)	0.1894 (3)	0.41314 (16)	0.0636 (7)
C15	0.4334 (6)	0.3111 (4)	0.4342 (2)	0.0945 (13)
H15	0.4625	0.3895	0.4031	0.113*
C16	0.3921 (6)	0.3082 (4)	0.5145 (2)	0.0962 (14)
H16A	0.2950	0.2896	0.5193	0.115*
H16B	0.4564	0.3969	0.5397	0.115*
C17	0.4072 (4)	0.1844 (4)	0.54418 (16)	0.0662 (7)
H17	0.5091	0.2224	0.5536	0.079*
C18	0.2062 (4)	−0.0101 (4)	0.47005 (19)	0.0787 (9)
H18A	0.1708	−0.0786	0.5097	0.118*
H18B	0.1820	−0.0591	0.4232	0.118*
H18C	0.1641	0.0495	0.4733	0.118*
C19	0.6100 (4)	−0.0104 (5)	0.2491 (2)	0.0798 (9)
H19A	0.6530	−0.0142	0.2951	0.120*
H19B	0.6575	0.0859	0.2309	0.120*
H19C	0.6187	−0.0714	0.2132	0.120*
C20	0.3316 (4)	0.1202 (4)	0.61604 (16)	0.0666 (7)
C21	0.2557 (5)	0.1608 (5)	0.6574 (2)	0.0890 (11)
H21	0.2395	0.2349	0.6449	0.107*
C22	0.3309 (5)	0.0067 (4)	0.65755 (19)	0.0811 (10)
H22	0.3760	−0.0442	0.6445	0.097*
C23	0.2530 (6)	−0.0120 (5)	0.7186 (2)	0.0945 (13)
H23	0.2352	−0.0801	0.7550	0.113*
C28	0.2589 (5)	−0.0637 (5)	0.0760 (2)	0.0899 (11)
H28A	0.2993	0.0371	0.0687	0.135*
H28B	0.1681	−0.1015	0.1003	0.135*
H28C	0.2464	−0.1097	0.0287	0.135*
C29	0.5002 (5)	−0.0388 (5)	0.0805 (2)	0.0889 (11)
H29A	0.5448	0.0623	0.0725	0.133*
H29B	0.4798	−0.0869	0.0334	0.133*
H29C	0.5634	−0.0595	0.1084	0.133*
C30	0.6367 (4)	0.2576 (4)	0.3367 (2)	0.0765 (9)
H30A	0.6734	0.2417	0.2913	0.115*
H30B	0.6800	0.2383	0.3783	0.115*
H30C	0.6583	0.3551	0.3387	0.115*
C26	0.1879 (4)	0.1905 (4)	0.25158 (17)	0.0678 (7)
C27	0.0320 (4)	0.1039 (5)	0.2602 (2)	0.0825 (10)
H27A	0.0089	0.0208	0.2895	0.124*
H27B	−0.0117	0.0751	0.2122	0.124*
H27C	−0.0027	0.1594	0.2848	0.124*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0970 (19)	0.1007 (19)	0.0769 (15)	0.0489 (16)	−0.0032 (13)	−0.0209 (14)
O7	0.0614 (12)	0.0638 (12)	0.0619 (10)	0.0335 (10)	0.0015 (8)	0.0059 (9)
O21	0.131 (3)	0.127 (3)	0.0648 (14)	0.071 (2)	0.0189 (14)	−0.0005 (14)
O31	0.093 (2)	0.116 (2)	0.143 (3)	0.0629 (19)	0.0174 (18)	0.062 (2)
C1	0.096 (2)	0.078 (2)	0.0585 (15)	0.059 (2)	0.0093 (15)	0.0031 (14)
C2	0.084 (2)	0.077 (2)	0.0698 (18)	0.0460 (19)	0.0099 (16)	−0.0026 (15)
C3	0.0707 (19)	0.088 (2)	0.0654 (16)	0.0456 (18)	0.0081 (14)	−0.0096 (15)
C4	0.077 (2)	0.087 (2)	0.0514 (14)	0.0460 (18)	0.0103 (13)	0.0032 (13)
C5	0.0681 (17)	0.0740 (19)	0.0484 (13)	0.0426 (16)	0.0078 (11)	0.0057 (11)
C6	0.0656 (17)	0.0738 (19)	0.0542 (14)	0.0384 (15)	0.0080 (12)	0.0151 (12)
C7	0.0582 (15)	0.0569 (16)	0.0576 (14)	0.0292 (13)	0.0037 (11)	0.0107 (11)
C8	0.0614 (16)	0.0579 (15)	0.0572 (14)	0.0307 (13)	−0.0001 (11)	0.0071 (11)
C9	0.0691 (17)	0.0639 (16)	0.0506 (13)	0.0408 (14)	0.0033 (11)	0.0057 (11)
C10	0.0691 (18)	0.0757 (18)	0.0544 (13)	0.0458 (16)	0.0057 (12)	0.0054 (12)
C11	0.104 (3)	0.085 (2)	0.0587 (16)	0.066 (2)	−0.0040 (15)	0.0049 (15)
C12	0.126 (3)	0.117 (3)	0.0620 (17)	0.094 (3)	0.0037 (18)	0.0130 (17)
C13	0.0583 (15)	0.0526 (14)	0.0528 (13)	0.0280 (12)	−0.0041 (11)	0.0005 (10)
C14	0.0760 (19)	0.0608 (17)	0.0567 (14)	0.0363 (16)	−0.0015 (13)	0.0044 (12)
C15	0.154 (4)	0.065 (2)	0.0712 (19)	0.060 (3)	0.019 (2)	0.0109 (16)
C16	0.154 (4)	0.063 (2)	0.0701 (19)	0.053 (3)	0.009 (2)	−0.0039 (15)
C17	0.0682 (18)	0.0650 (18)	0.0589 (15)	0.0284 (15)	−0.0061 (12)	−0.0073 (12)
C18	0.0605 (18)	0.087 (2)	0.0677 (17)	0.0210 (17)	−0.0013 (14)	−0.0166 (15)
C19	0.075 (2)	0.103 (3)	0.076 (2)	0.055 (2)	0.0063 (16)	0.0012 (17)
C20	0.0689 (18)	0.0732 (19)	0.0520 (13)	0.0314 (15)	−0.0093 (12)	−0.0096 (13)
C21	0.115 (3)	0.096 (3)	0.068 (2)	0.063 (3)	−0.0002 (18)	−0.0086 (17)
C22	0.095 (3)	0.092 (3)	0.0616 (17)	0.051 (2)	−0.0005 (15)	0.0046 (16)
C23	0.118 (3)	0.102 (3)	0.0589 (17)	0.053 (3)	0.0040 (19)	0.0060 (17)
C28	0.114 (3)	0.113 (3)	0.0594 (17)	0.069 (3)	−0.0114 (18)	−0.0040 (18)
C29	0.093 (3)	0.110 (3)	0.0641 (18)	0.051 (2)	0.0253 (17)	0.0080 (18)
C30	0.0626 (19)	0.080 (2)	0.082 (2)	0.0325 (17)	−0.0036 (15)	0.0039 (16)
C26	0.0720 (19)	0.078 (2)	0.0634 (16)	0.0447 (17)	−0.0037 (14)	0.0005 (14)
C27	0.070 (2)	0.090 (3)	0.090 (2)	0.0419 (19)	−0.0140 (17)	−0.0177 (19)

Geometric parameters (Å, º) top

O3—C3	1.223 (4)	C13—C14	1.521 (4)
O7—C26	1.345 (4)	C13—C18	1.521 (4)
O7—C7	1.454 (3)	C13—C17	1.560 (4)
O21—C23	1.333 (6)	C14—C15	1.323 (5)
O21—C21	1.375 (5)	C15—C16	1.507 (5)
O31—C26	1.195 (4)	C15—H15	0.9300
C1—C2	1.357 (5)	C16—C17	1.524 (5)
C1—C10	1.495 (5)	C16—H16A	0.9700
C1—H1	0.9300	C16—H16B	0.9700
C2—C3	1.457 (5)	C17—C20	1.501 (4)
C2—H2	0.9300	C17—H17	0.9800
C3—C4	1.524 (5)	C18—H18A	0.9600
C4—C28	1.531 (5)	C18—H18B	0.9600
C4—C29	1.550 (5)	C18—H18C	0.9600
C4—C5	1.553 (4)	C19—H19A	0.9600
C5—C6	1.523 (5)	C19—H19B	0.9600
C5—C10	1.551 (4)	C19—H19C	0.9600
C5—H5	0.9800	C20—C21	1.334 (5)
C6—C7	1.523 (4)	C20—C22	1.434 (5)
C6—H6A	0.9700	C21—H21	0.9300
C6—H6B	0.9700	C22—C23	1.337 (6)
C7—C8	1.544 (4)	C22—H22	0.9300
C7—H7	0.9800	C23—H23	0.9300
C8—C14	1.531 (4)	C28—H28A	0.9600
C8—C30	1.548 (5)	C28—H28B	0.9600
C8—C9	1.556 (4)	C28—H28C	0.9600
C9—C11	1.546 (4)	C29—H29A	0.9600
C9—C10	1.570 (4)	C29—H29B	0.9600
C9—H9	0.9800	C29—H29C	0.9600
C10—C19	1.548 (5)	C30—H30A	0.9600
C11—C12	1.474 (5)	C30—H30B	0.9600
C11—H11A	0.9700	C30—H30C	0.9600
C11—H11B	0.9700	C26—C27	1.472 (5)
C12—C13	1.517 (4)	C27—H27A	0.9600
C12—H12A	0.9700	C27—H27B	0.9600
C12—H12B	0.9700	C27—H27C	0.9600

C26—O7—C7	118.1 (2)	C18—C13—C17	109.8 (2)
C23—O21—C21	105.6 (3)	C15—C14—C13	110.6 (3)
C2—C1—C10	124.0 (3)	C15—C14—C8	127.6 (3)
C2—C1—H1	118.0	C13—C14—C8	121.5 (3)
C10—C1—H1	118.0	C14—C15—C16	112.3 (3)
C1—C2—C3	122.4 (3)	C14—C15—H15	123.9
C1—C2—H2	118.8	C16—C15—H15	123.9
C3—C2—H2	118.8	C15—C16—C17	101.1 (3)
O3—C3—C2	119.2 (4)	C15—C16—H16A	111.6
O3—C3—C4	121.1 (3)	C17—C16—H16A	111.6
C2—C3—C4	119.6 (3)	C15—C16—H16B	111.6
C3—C4—C28	108.6 (3)	C17—C16—H16B	111.6
C3—C4—C29	107.1 (3)	H16A—C16—H16B	109.4
C28—C4—C29	107.7 (3)	C20—C17—C16	115.8 (3)
C3—C4—C5	109.4 (2)	C20—C17—C13	116.9 (3)
C28—C4—C5	109.2 (3)	C16—C17—C13	104.0 (3)
C29—C4—C5	114.7 (3)	C20—C17—H17	106.5
C6—C5—C10	111.8 (3)	C16—C17—H17	106.5
C6—C5—C4	115.5 (2)	C13—C17—H17	106.5
C10—C5—C4	115.5 (2)	C13—C18—H18A	109.5
C6—C5—H5	104.1	C13—C18—H18B	109.5
C10—C5—H5	104.1	H18A—C18—H18B	109.5
C4—C5—H5	104.1	C13—C18—H18C	109.5
C7—C6—C5	111.2 (2)	H18A—C18—H18C	109.5
C7—C6—H6A	109.4	H18B—C18—H18C	109.5
C5—C6—H6A	109.4	C10—C19—H19A	109.5
C7—C6—H6B	109.4	C10—C19—H19B	109.5
C5—C6—H6B	109.4	H19A—C19—H19B	109.5
H6A—C6—H6B	108.0	C10—C19—H19C	109.5
O7—C7—C6	107.9 (2)	H19A—C19—H19C	109.5
O7—C7—C8	108.2 (2)	H19B—C19—H19C	109.5
C6—C7—C8	112.3 (2)	C21—C20—C22	104.5 (3)
O7—C7—H7	109.5	C21—C20—C17	127.6 (3)
C6—C7—H7	109.5	C22—C20—C17	127.8 (3)
C8—C7—H7	109.5	C20—C21—O21	111.6 (4)
C14—C8—C7	111.2 (2)	C20—C21—H21	124.2
C14—C8—C30	106.1 (3)	O21—C21—H21	124.2
C7—C8—C30	106.9 (2)	C23—C22—C20	106.9 (4)
C14—C8—C9	108.3 (2)	C23—C22—H22	126.5
C7—C8—C9	109.7 (2)	C20—C22—H22	126.5
C30—C8—C9	114.6 (3)	O21—C23—C22	111.3 (4)
C11—C9—C8	110.4 (3)	O21—C23—H23	124.4
C11—C9—C10	114.4 (2)	C22—C23—H23	124.4
C8—C9—C10	115.6 (2)	C4—C28—H28A	109.5
C11—C9—H9	105.1	C4—C28—H28B	109.5
C8—C9—H9	105.1	H28A—C28—H28B	109.5
C10—C9—H9	105.1	C4—C28—H28C	109.5
C1—C10—C5	108.1 (3)	H28A—C28—H28C	109.5
C1—C10—C19	106.0 (3)	H28B—C28—H28C	109.5
C5—C10—C19	115.6 (3)	C4—C29—H29A	109.5
C1—C10—C9	108.6 (2)	C4—C29—H29B	109.5
C5—C10—C9	106.0 (2)	H29A—C29—H29B	109.5
C19—C10—C9	112.4 (3)	C4—C29—H29C	109.5
C12—C11—C9	114.5 (3)	H29A—C29—H29C	109.5
C12—C11—H11A	108.6	H29B—C29—H29C	109.5
C9—C11—H11A	108.6	C8—C30—H30A	109.5
C12—C11—H11B	108.6	C8—C30—H30B	109.5
C9—C11—H11B	108.6	H30A—C30—H30B	109.5
H11A—C11—H11B	107.6	C8—C30—H30C	109.5
C11—C12—C13	118.1 (2)	H30A—C30—H30C	109.5
C11—C12—H12A	107.8	H30B—C30—H30C	109.5
C13—C12—H12A	107.8	O31—C26—O7	122.6 (3)
C11—C12—H12B	107.8	O31—C26—C27	125.1 (3)
C13—C12—H12B	107.8	O7—C26—C27	112.3 (3)
H12A—C12—H12B	107.1	C26—C27—H27A	109.5
C12—C13—C14	111.9 (3)	C26—C27—H27B	109.5
C12—C13—C18	112.0 (3)	H27A—C27—H27B	109.5
C14—C13—C18	109.3 (2)	C26—C27—H27C	109.5
C12—C13—C17	113.1 (2)	H27A—C27—H27C	109.5
C14—C13—C17	100.1 (2)	H27B—C27—H27C	109.5

C10—C1—C2—C3	2.1 (5)	C8—C9—C10—C5	−54.8 (3)
C1—C2—C3—O3	174.2 (3)	C11—C9—C10—C19	−57.5 (4)
C1—C2—C3—C4	−4.2 (5)	C8—C9—C10—C19	72.4 (3)
O3—C3—C4—C28	41.7 (4)	C8—C9—C11—C12	53.9 (4)
C2—C3—C4—C28	−139.9 (3)	C10—C9—C11—C12	−173.6 (3)
O3—C3—C4—C29	−74.4 (4)	C9—C11—C12—C13	−6.5 (6)
C2—C3—C4—C29	104.1 (3)	C11—C12—C13—C14	−35.3 (5)
O3—C3—C4—C5	160.8 (3)	C11—C12—C13—C18	87.8 (5)
C2—C3—C4—C5	−20.8 (4)	C11—C12—C13—C17	−147.5 (4)
C3—C4—C5—C6	−177.5 (3)	C12—C13—C14—C15	−142.2 (4)
C28—C4—C5—C6	−58.8 (4)	C18—C13—C14—C15	93.2 (4)
C29—C4—C5—C6	62.2 (4)	C17—C13—C14—C15	−22.1 (4)
C3—C4—C5—C10	49.3 (4)	C12—C13—C14—C8	32.3 (4)
C28—C4—C5—C10	168.0 (3)	C18—C13—C14—C8	−92.3 (3)
C29—C4—C5—C10	−71.0 (4)	C17—C13—C14—C8	152.4 (3)
C10—C5—C6—C7	−61.6 (3)	C7—C8—C14—C15	−53.5 (5)
C4—C5—C6—C7	163.5 (3)	C30—C8—C14—C15	62.5 (5)
C26—O7—C7—C6	−85.6 (3)	C9—C8—C14—C15	−174.1 (4)
C26—O7—C7—C8	152.6 (3)	C7—C8—C14—C13	133.0 (3)
C5—C6—C7—O7	−62.6 (3)	C30—C8—C14—C13	−111.0 (3)
C5—C6—C7—C8	56.6 (3)	C9—C8—C14—C13	12.4 (4)
O7—C7—C8—C14	−51.3 (3)	C13—C14—C15—C16	2.2 (6)
C6—C7—C8—C14	−170.3 (3)	C8—C14—C15—C16	−171.9 (4)
O7—C7—C8—C30	−166.7 (3)	C14—C15—C16—C17	19.4 (6)
C6—C7—C8—C30	74.3 (3)	C15—C16—C17—C20	−161.5 (4)
O7—C7—C8—C9	68.5 (3)	C15—C16—C17—C13	−31.9 (4)
C6—C7—C8—C9	−50.5 (3)	C12—C13—C17—C20	−78.9 (4)
C14—C8—C9—C11	−54.7 (3)	C14—C13—C17—C20	161.9 (3)
C7—C8—C9—C11	−176.3 (3)	C18—C13—C17—C20	47.0 (4)
C30—C8—C9—C11	63.4 (3)	C12—C13—C17—C16	152.2 (3)
C14—C8—C9—C10	173.5 (3)	C14—C13—C17—C16	32.9 (3)
C7—C8—C9—C10	51.9 (3)	C18—C13—C17—C16	−82.0 (4)
C30—C8—C9—C10	−68.4 (3)	C16—C17—C20—C21	−1.4 (5)
C2—C1—C10—C5	24.6 (4)	C13—C17—C20—C21	−124.5 (4)
C2—C1—C10—C19	−100.0 (4)	C16—C17—C20—C22	−177.9 (4)
C2—C1—C10—C9	139.0 (3)	C13—C17—C20—C22	59.0 (5)
C6—C5—C10—C1	174.4 (2)	C22—C20—C21—O21	−1.5 (5)
C4—C5—C10—C1	−50.8 (3)	C17—C20—C21—O21	−178.6 (3)
C6—C5—C10—C19	−67.1 (3)	C23—O21—C21—C20	1.3 (5)
C4—C5—C10—C19	67.8 (4)	C21—C20—C22—C23	1.2 (5)
C6—C5—C10—C9	58.1 (3)	C17—C20—C22—C23	178.3 (4)
C4—C5—C10—C9	−167.0 (3)	C21—O21—C23—C22	−0.4 (5)
C11—C9—C10—C1	59.4 (4)	C20—C22—C23—O21	−0.4 (5)
C8—C9—C10—C1	−170.7 (3)	C7—O7—C26—O31	−3.6 (5)
C11—C9—C10—C5	175.3 (3)	C7—O7—C26—C27	174.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O3ⁱ	0.93	2.52	3.431 (4)	166
C11—H11A···O3ⁱ	0.97	2.66	3.628 (5)	175
C27—H27A···O21ⁱⁱ	0.96	2.76	3.684 (6)	162

Symmetry codes: (i) −y, x−y−1, z+1/3; (ii) −x+y, −x, z−1/3.

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