Ophiobolin A

The title compound, namely (2′S,3′S,3aR,5′R,6aS,9R,9aS,10aR)-1,3a,4,4′,5′,6a,7,8,9,9a,10,10a-dodeca­hydro-9-hydr­oxy-3′,9,10a-trimethyl-5′-(2-methyl­propen-1-yl)-7-oxospiro[dicyclo­penta­[a,d]cyclo­octene-3(2H),2′(3′H)-furan]-6-carbaldehyde, C₂₅H₃₆O₄, displays phytotoxic behaviour that may be correlated with some structural features of the mol­ecule. The eight-membered ring of the terpenoid tricyclic skeleton is cis- and trans-joined with the fused five-membered rings. One intra­molecular O—H...O hydrogen bond and two inter­molecular C—H...O hydrogen bonds are present.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.054
• wR factor = 0.114
• Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.112
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.35 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.50 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C24

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               2208
           Count of symmetry unique reflns         2244
           Completeness (_total/calc)             98.40%
           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
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(2'S,3'S,3aR,5'R,6aS,9R,9aS,10aR)-1,3a,4,4',5',6a,7,8,9,9a,10,10a- dodecahydro-9-hydroxy-3',9,10a-trimethyl-5'-(2-methylpropen-1-yl)-7- oxospiro[dicyclopenta[a,d]cyclooctene-3(2H),2'(3'H)-furan]-6-carbaldehyde

Crystal data

C25H36O4	F(000) = 872
Mr = 400.54	Dx = 1.210 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 192 reflections
a = 7.251 (4) Å	θ = 4.1–24.2°
b = 14.756 (9) Å	µ = 0.08 mm^−1
c = 20.55 (2) Å	T = 173 K
V = 2199 (3) Å^3	Prism, colourless
Z = 4	0.20 × 0.20 × 0.07 mm

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	2208 independent reflections
Radiation source: fine-focus sealed tube	1356 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.112
Detector resolution: 9 pixels mm^-1	θmax = 25.0°, θmin = 3°
Thick–slice φ and ω scans	h = −8→7
Absorption correction: multi-scan (SADABS; Bruker Nonius, 2002)	k = −17→16
Tmin = 0.980, Tmax = 0.994	l = −24→20
7226 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0367P)^2 + 0.6026P] where P = (Fo^2 + 2Fc^2)/3
2208 reflections	(Δ/σ)max < 0.001
267 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.9599 (4)	0.5785 (2)	0.55823 (15)	0.0298 (9)
H1	0.9345	0.6298	0.5430	0.030*
O2	1.2591 (5)	0.6516 (2)	0.38921 (19)	0.0384 (10)
O3	0.9319 (5)	0.7256 (2)	0.47325 (18)	0.0359 (9)
O4	0.2862 (4)	0.4017 (2)	0.32500 (14)	0.0254 (8)
C1	0.7966 (6)	0.4362 (3)	0.4762 (2)	0.0209 (11)
H1A	0.7113	0.4865	0.4866	0.021*
H1B	0.8068	0.3982	0.5158	0.021*
C2	0.9863 (6)	0.4771 (3)	0.4628 (2)	0.0206 (12)
H2	1.0666	0.4256	0.4488	0.021*
C3	1.0823 (6)	0.5195 (3)	0.5234 (2)	0.0224 (12)
C4	1.2423 (6)	0.5728 (3)	0.4925 (2)	0.0275 (13)
H4A	1.2709	0.6273	0.5188	0.027*
H4B	1.3543	0.5346	0.4900	0.027*
C5	1.1801 (7)	0.5999 (3)	0.4252 (3)	0.0271 (12)
C6	1.0028 (6)	0.5502 (3)	0.4086 (2)	0.0234 (12)
H6	1.0236	0.5177	0.3665	0.023*
C7	0.8372 (7)	0.6116 (3)	0.3993 (2)	0.0233 (12)
C8	0.6930 (7)	0.5878 (3)	0.3629 (2)	0.0252 (12)
H8	0.5968	0.6311	0.3589	0.025*
C9	0.6670 (7)	0.4999 (3)	0.3277 (2)	0.0255 (12)
H9A	0.7875	0.4774	0.3119	0.025*
H9B	0.5856	0.5091	0.2896	0.025*
C10	0.5805 (6)	0.4298 (3)	0.3739 (2)	0.0163 (11)
H10	0.4943	0.4655	0.4019	0.016*
C11	0.7058 (6)	0.3780 (3)	0.4225 (2)	0.0202 (11)
C12	0.5579 (7)	0.3157 (3)	0.4529 (2)	0.0244 (12)
H12A	0.6161	0.2613	0.4722	0.024*
H12B	0.4895	0.3482	0.4874	0.024*
C13	0.4280 (7)	0.2888 (3)	0.3977 (2)	0.0254 (12)
H13A	0.2983	0.2909	0.4127	0.025*
H13B	0.4557	0.2265	0.3827	0.025*
C14	0.4586 (6)	0.3572 (3)	0.3417 (2)	0.0247 (12)
C15	0.5354 (7)	0.3191 (3)	0.2756 (2)	0.0277 (13)
H15	0.6659	0.3397	0.2704	0.028*
C16	0.4164 (7)	0.3667 (4)	0.2242 (2)	0.0307 (13)
H16A	0.4723	0.4250	0.2108	0.031*
H16B	0.4002	0.3280	0.1853	0.031*
C17	0.2326 (7)	0.3818 (3)	0.2591 (2)	0.0285 (13)
H17	0.1573	0.3251	0.2579	0.029*
C18	0.1223 (6)	0.4595 (4)	0.2337 (2)	0.0318 (14)
H18	0.1508	0.5172	0.2514	0.032*
C19	−0.0096 (7)	0.4577 (4)	0.1898 (2)	0.0363 (14)
C20	1.1435 (7)	0.4498 (4)	0.5724 (2)	0.0334 (14)
H20A	1.2119	0.4798	0.6075	0.033*
H20B	1.2232	0.4052	0.5511	0.033*
H20C	1.0351	0.4192	0.5906	0.033*
C21	0.8247 (7)	0.6984 (4)	0.4332 (3)	0.0312 (13)
H21	0.7233	0.7364	0.4227	0.031*
C22	0.8522 (6)	0.3181 (3)	0.3887 (2)	0.0226 (12)
H22A	0.9302	0.3560	0.3608	0.023*
H22B	0.7906	0.2720	0.3622	0.023*
H22C	0.9288	0.2885	0.4218	0.023*
C23	0.5289 (8)	0.2167 (4)	0.2665 (3)	0.0403 (15)
H23A	0.4008	0.1958	0.2695	0.040*
H23B	0.6027	0.1873	0.3004	0.040*
H23C	0.5788	0.2010	0.2236	0.040*
C24	−0.1017 (8)	0.5426 (5)	0.1668 (3)	0.0556 (19)
H24A	−0.0512	0.5947	0.1904	0.056*
H24B	−0.2347	0.5384	0.1749	0.056*
H24C	−0.0797	0.5503	0.1201	0.056*
C25	−0.0768 (8)	0.3725 (5)	0.1568 (3)	0.0542 (19)
H25A	−0.0414	0.3737	0.1108	0.054*
H25B	−0.2114	0.3689	0.1603	0.054*
H25C	−0.0213	0.3195	0.1779	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.032 (2)	0.024 (2)	0.034 (2)	0.0062 (16)	0.0032 (17)	−0.0072 (17)
O2	0.029 (2)	0.041 (2)	0.045 (2)	−0.0038 (18)	0.0115 (19)	0.009 (2)
O3	0.041 (2)	0.023 (2)	0.044 (2)	0.0047 (18)	−0.006 (2)	−0.0072 (19)
O4	0.0224 (18)	0.038 (2)	0.0154 (18)	0.0064 (16)	−0.0032 (15)	−0.0013 (16)
C1	0.020 (3)	0.021 (3)	0.022 (3)	0.004 (2)	−0.002 (2)	0.004 (2)
C2	0.019 (3)	0.023 (3)	0.020 (3)	0.003 (2)	0.000 (2)	−0.002 (2)
C3	0.019 (3)	0.023 (3)	0.025 (3)	−0.001 (2)	0.001 (2)	−0.003 (2)
C4	0.018 (3)	0.029 (3)	0.035 (3)	−0.005 (2)	−0.002 (2)	−0.009 (2)
C5	0.017 (3)	0.027 (3)	0.037 (3)	0.005 (2)	0.006 (2)	−0.001 (3)
C6	0.026 (3)	0.024 (3)	0.020 (3)	0.004 (2)	0.006 (2)	−0.002 (2)
C7	0.026 (3)	0.019 (3)	0.024 (3)	0.001 (2)	0.003 (2)	0.000 (2)
C8	0.027 (3)	0.019 (3)	0.029 (3)	0.001 (2)	0.007 (2)	0.009 (2)
C9	0.028 (3)	0.032 (3)	0.016 (3)	−0.003 (2)	−0.003 (2)	0.007 (2)
C10	0.018 (2)	0.017 (3)	0.015 (3)	−0.001 (2)	0.004 (2)	−0.002 (2)
C11	0.021 (3)	0.022 (3)	0.018 (3)	−0.002 (2)	−0.002 (2)	0.002 (2)
C12	0.027 (3)	0.027 (3)	0.019 (3)	−0.007 (2)	−0.004 (2)	0.002 (2)
C13	0.025 (3)	0.026 (3)	0.025 (3)	−0.004 (2)	0.004 (2)	0.000 (2)
C14	0.018 (3)	0.028 (3)	0.028 (3)	0.008 (2)	0.000 (2)	−0.003 (2)
C15	0.022 (3)	0.033 (3)	0.028 (3)	0.003 (2)	0.002 (2)	−0.002 (3)
C16	0.023 (3)	0.048 (4)	0.021 (3)	0.001 (3)	−0.001 (2)	−0.002 (3)
C17	0.024 (3)	0.042 (3)	0.020 (3)	0.000 (3)	−0.004 (2)	−0.007 (3)
C18	0.026 (3)	0.042 (4)	0.027 (3)	0.003 (3)	0.004 (3)	0.006 (3)
C19	0.020 (3)	0.069 (4)	0.020 (3)	0.011 (3)	0.005 (2)	0.010 (3)
C20	0.037 (3)	0.035 (4)	0.028 (3)	−0.002 (3)	−0.008 (3)	−0.005 (3)
C21	0.034 (3)	0.023 (3)	0.036 (3)	0.008 (3)	0.005 (3)	0.005 (3)
C22	0.023 (3)	0.022 (3)	0.023 (3)	0.000 (2)	−0.007 (2)	−0.003 (2)
C23	0.036 (3)	0.050 (4)	0.035 (4)	−0.001 (3)	−0.007 (3)	−0.009 (3)
C24	0.040 (4)	0.088 (5)	0.039 (4)	0.019 (4)	0.004 (3)	0.026 (4)
C25	0.032 (3)	0.096 (6)	0.034 (4)	0.007 (3)	−0.007 (3)	−0.004 (4)

Geometric parameters (Å, º)

O1—C3	1.434 (5)	C12—H12A	0.9900
O1—H1	0.8400	C12—H12B	0.9900
O2—C5	1.207 (6)	C13—C14	1.546 (7)
O3—C21	1.202 (6)	C13—H13A	0.9900
O4—C17	1.439 (6)	C13—H13B	0.9900
O4—C14	1.453 (5)	C14—C15	1.573 (7)
C1—C2	1.527 (6)	C15—C23	1.524 (7)
C1—C11	1.546 (6)	C15—C16	1.534 (7)
C1—H1A	0.9900	C15—H15	1.0000
C1—H1B	0.9900	C16—C17	1.530 (7)
C2—C6	1.556 (6)	C16—H16A	0.9900
C2—C3	1.557 (6)	C16—H16B	0.9900
C2—H2	1.0000	C17—C18	1.491 (7)
C3—C20	1.506 (7)	C17—H17	1.0000
C3—C4	1.539 (7)	C18—C19	1.315 (7)
C4—C5	1.509 (7)	C18—H18	0.9500
C4—H4A	0.9900	C19—C24	1.496 (8)
C4—H4B	0.9900	C19—C25	1.510 (8)
C5—C6	1.519 (7)	C20—H20A	0.9800
C6—C7	1.515 (6)	C20—H20B	0.9800
C6—H6	1.0000	C20—H20C	0.9800
C7—C8	1.332 (7)	C21—H21	0.9500
C7—C21	1.460 (7)	C22—H22A	0.9800
C8—C9	1.497 (7)	C22—H22B	0.9800
C8—H8	0.9500	C22—H22C	0.9800
C9—C10	1.537 (6)	C23—H23A	0.9800
C9—H9A	0.9900	C23—H23B	0.9800
C9—H9B	0.9900	C23—H23C	0.9800
C10—C14	1.538 (6)	C24—H24A	0.9800
C10—C11	1.551 (6)	C24—H24B	0.9800
C10—H10	1.0000	C24—H24C	0.9800
C11—C12	1.544 (6)	C25—H25A	0.9800
C11—C22	1.546 (6)	C25—H25B	0.9800
C12—C13	1.527 (6)	C25—H25C	0.9800
C3—O1—H1	119.8	C14—C13—H13A	110.3
C17—O4—C14	111.3 (3)	C12—C13—H13B	110.3
C2—C1—C11	118.3 (4)	C14—C13—H13B	110.3
C2—C1—H1A	107.7	H13A—C13—H13B	108.5
C11—C1—H1A	107.7	O4—C14—C10	106.3 (4)
C2—C1—H1B	107.7	O4—C14—C13	110.3 (4)
C11—C1—H1B	107.7	C10—C14—C13	102.5 (4)
H1A—C1—H1B	107.1	O4—C14—C15	105.2 (4)
C1—C2—C6	118.2 (4)	C10—C14—C15	114.7 (4)
C1—C2—C3	114.7 (4)	C13—C14—C15	117.4 (4)
C6—C2—C3	105.0 (4)	C23—C15—C16	110.6 (4)
C1—C2—H2	106.0	C23—C15—C14	116.8 (4)
C6—C2—H2	106.0	C16—C15—C14	103.4 (4)
C3—C2—H2	106.0	C23—C15—H15	108.6
O1—C3—C20	105.2 (4)	C16—C15—H15	108.6
O1—C3—C4	111.2 (4)	C14—C15—H15	108.6
C20—C3—C4	113.8 (4)	C17—C16—C15	103.5 (4)
O1—C3—C2	111.5 (4)	C17—C16—H16A	111.1
C20—C3—C2	113.1 (4)	C15—C16—H16A	111.1
C4—C3—C2	102.3 (4)	C17—C16—H16B	111.1
C5—C4—C3	106.7 (4)	C15—C16—H16B	111.1
C5—C4—H4A	110.4	H16A—C16—H16B	109.0
C3—C4—H4A	110.4	O4—C17—C18	108.5 (4)
C5—C4—H4B	110.4	O4—C17—C16	103.6 (4)
C3—C4—H4B	110.4	C18—C17—C16	114.5 (4)
H4A—C4—H4B	108.6	O4—C17—H17	110.0
O2—C5—C4	125.9 (5)	C18—C17—H17	110.0
O2—C5—C6	124.7 (5)	C16—C17—H17	110.0
C4—C5—C6	109.3 (4)	C19—C18—C17	128.0 (6)
C7—C6—C5	114.2 (4)	C19—C18—H18	116.0
C7—C6—C2	116.3 (4)	C17—C18—H18	116.0
C5—C6—C2	103.8 (4)	C18—C19—C24	121.7 (6)
C7—C6—H6	107.3	C18—C19—C25	124.0 (6)
C5—C6—H6	107.3	C24—C19—C25	114.3 (5)
C2—C6—H6	107.3	C3—C20—H20A	109.5
C8—C7—C21	116.7 (5)	C3—C20—H20B	109.5
C8—C7—C6	122.3 (4)	H20A—C20—H20B	109.5
C21—C7—C6	120.9 (4)	C3—C20—H20C	109.5
C7—C8—C9	126.7 (4)	H20A—C20—H20C	109.5
C7—C8—H8	116.6	H20B—C20—H20C	109.5
C9—C8—H8	116.6	O3—C21—C7	125.4 (5)
C8—C9—C10	109.6 (4)	O3—C21—H21	117.3
C8—C9—H9A	109.7	C7—C21—H21	117.3
C10—C9—H9A	109.7	C11—C22—H22A	109.5
C8—C9—H9B	109.7	C11—C22—H22B	109.5
C10—C9—H9B	109.7	H22A—C22—H22B	109.5
H9A—C9—H9B	108.2	C11—C22—H22C	109.5
C9—C10—C14	115.9 (4)	H22A—C22—H22C	109.5
C9—C10—C11	119.3 (4)	H22B—C22—H22C	109.5
C14—C10—C11	105.6 (4)	C15—C23—H23A	109.5
C9—C10—H10	104.8	C15—C23—H23B	109.5
C14—C10—H10	104.8	H23A—C23—H23B	109.5
C11—C10—H10	104.8	C15—C23—H23C	109.5
C12—C11—C22	108.6 (4)	H23A—C23—H23C	109.5
C12—C11—C1	109.7 (4)	H23B—C23—H23C	109.5
C22—C11—C1	110.2 (4)	C19—C24—H24A	109.5
C12—C11—C10	98.5 (4)	C19—C24—H24B	109.5
C22—C11—C10	113.3 (4)	H24A—C24—H24B	109.5
C1—C11—C10	115.8 (4)	C19—C24—H24C	109.5
C13—C12—C11	106.4 (4)	H24A—C24—H24C	109.5
C13—C12—H12A	110.5	H24B—C24—H24C	109.5
C11—C12—H12A	110.5	C19—C25—H25A	109.5
C13—C12—H12B	110.5	C19—C25—H25B	109.5
C11—C12—H12B	110.5	H25A—C25—H25B	109.5
H12A—C12—H12B	108.6	C19—C25—H25C	109.5
C12—C13—C14	107.1 (4)	H25A—C25—H25C	109.5
C12—C13—H13A	110.3	H25B—C25—H25C	109.5
C11—C1—C2—C6	65.8 (6)	C9—C10—C11—C1	66.0 (5)
C11—C1—C2—C3	−169.4 (4)	C14—C10—C11—C1	−161.3 (4)
C1—C2—C3—O1	−48.5 (5)	C22—C11—C12—C13	−80.6 (5)
C6—C2—C3—O1	82.9 (4)	C1—C11—C12—C13	158.9 (4)
C1—C2—C3—C20	69.8 (5)	C10—C11—C12—C13	37.5 (5)
C6—C2—C3—C20	−158.8 (4)	C11—C12—C13—C14	−17.9 (5)
C1—C2—C3—C4	−167.5 (4)	C17—O4—C14—C10	132.1 (4)
C6—C2—C3—C4	−36.0 (4)	C17—O4—C14—C13	−117.4 (4)
O1—C3—C4—C5	−90.6 (5)	C17—O4—C14—C15	10.1 (5)
C20—C3—C4—C5	150.9 (4)	C9—C10—C14—O4	−75.1 (5)
C2—C3—C4—C5	28.6 (5)	C11—C10—C14—O4	150.3 (4)
C3—C4—C5—O2	170.4 (5)	C9—C10—C14—C13	169.0 (4)
C3—C4—C5—C6	−10.7 (5)	C11—C10—C14—C13	34.5 (4)
O2—C5—C6—C7	−65.3 (6)	C9—C10—C14—C15	40.6 (5)
C4—C5—C6—C7	115.8 (5)	C11—C10—C14—C15	−93.9 (4)
O2—C5—C6—C2	167.0 (5)	C12—C13—C14—O4	−122.9 (4)
C4—C5—C6—C2	−11.9 (5)	C12—C13—C14—C10	−9.9 (5)
C1—C2—C6—C7	32.8 (6)	C12—C13—C14—C15	116.7 (4)
C3—C2—C6—C7	−96.6 (5)	O4—C14—C15—C23	−108.6 (5)
C1—C2—C6—C5	159.2 (4)	C10—C14—C15—C23	135.0 (5)
C3—C2—C6—C5	29.8 (4)	C13—C14—C15—C23	14.5 (6)
C5—C6—C7—C8	154.9 (5)	O4—C14—C15—C16	13.1 (5)
C2—C6—C7—C8	−84.1 (6)	C10—C14—C15—C16	−103.3 (5)
C5—C6—C7—C21	−28.4 (7)	C13—C14—C15—C16	136.2 (4)
C2—C6—C7—C21	92.6 (5)	C23—C15—C16—C17	95.9 (5)
C21—C7—C8—C9	−175.2 (4)	C14—C15—C16—C17	−29.9 (5)
C6—C7—C8—C9	1.6 (8)	C14—O4—C17—C18	−151.4 (4)
C7—C8—C9—C10	86.2 (6)	C14—O4—C17—C16	−29.3 (5)
C8—C9—C10—C14	150.4 (4)	C15—C16—C17—O4	36.3 (5)
C8—C9—C10—C11	−81.5 (5)	C15—C16—C17—C18	154.3 (4)
C2—C1—C11—C12	159.0 (4)	O4—C17—C18—C19	−150.5 (5)
C2—C1—C11—C22	39.5 (5)	C16—C17—C18—C19	94.3 (6)
C2—C1—C11—C10	−90.7 (5)	C17—C18—C19—C24	−176.9 (5)
C9—C10—C11—C12	−177.2 (4)	C17—C18—C19—C25	1.0 (9)
C14—C10—C11—C12	−44.5 (4)	C8—C7—C21—O3	171.4 (5)
C9—C10—C11—C22	−62.7 (5)	C6—C7—C21—O3	−5.4 (8)
C14—C10—C11—C22	70.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.84	2.01	2.794 (5)	154
C4—H4A···O3^i	0.99	2.47	3.352 (6)	148
C8—H8···O2^ii	0.95	2.54	3.328 (6)	140

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) x−1, y, z.