Methyl 12-benzoyl­dehydro­abietate

The title compound, C₂₈H₃₄O₃, is a new derivative of dehydro­abietic acid, whose A and B rings exhibit a classical chair and half-chair conformation, respectively.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.088
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT024_ALERT_4_B Merging of Friedel Pairs is STRONGLY Indicated .          !

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.836     0.985
            Tmin(prime) and Tmax expected:      0.973     0.985
            RR(prime) =      0.859
            Please check that your absorption correction is appropriate.
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack   -0.900
           From the CIF: _refine_ls_abs_structure_Flack_su    1.100
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ...       1.10
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......      -0.90
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.86
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.54 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C18    -   C19     ..       6.16 su

Alert level G
REFLT03_ALERT_4_G  ALERT: MoKa measured Friedel data cannot be used to
                   determine absolute structure in a light-atom
                   study EXCEPT under VERY special conditions.
                   It is preferred that Friedel data is merged in such cases.
           From the CIF: _diffrn_reflns_theta_max           25.35
           From the CIF: _reflns_number_total               4202
           Count of symmetry unique reflns         2356
           Completeness (_total/calc)            178.35%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1846
           Fraction of Friedel pairs measured     0.784
           Are heavy atom types Z>Si present         no

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

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

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Computing details

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Methyl 12-benzoyldehydroabietate

Crystal data

C28H34O3	F(000) = 904
Mr = 418.55	Dx = 1.196 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: c 2y	Cell parameters from 4618 reflections
a = 14.0617 (13) Å	θ = 3.0–25.3°
b = 6.0363 (5) Å	µ = 0.08 mm^−1
c = 28.051 (4) Å	T = 193 K
β = 102.40 (2)°	Block, colorless
V = 2325.4 (4) Å^3	0.35 × 0.30 × 0.20 mm
Z = 4

Data collection

Rigaku Mercury CCD diffractometer	4202 independent reflections
Radiation source: fine-focus sealed tube	3794 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 7.31 pixels mm^-1	θmax = 25.4°, θmin = 3.0°
ω scans	h = −16→16
Absorption correction: multi-scan REQABS (Jacobson, 1998)	k = −7→7
Tmin = 0.836, Tmax = 0.985	l = −33→28
11429 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 0.4191P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
4202 reflections	Δρmax = 0.11 e Å^−3
285 parameters	Δρmin = −0.14 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1846 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.9 (11)

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	0.69767 (9)	0.0447 (3)	0.16653 (5)	0.0456 (4)
O2	1.13050 (11)	0.8147 (2)	0.45567 (6)	0.0537 (4)
O3	1.08690 (10)	0.4684 (2)	0.43672 (5)	0.0423 (4)
C1	0.82468 (12)	0.4038 (3)	0.23174 (6)	0.0247 (4)
H1	0.7610	0.4320	0.2366	0.030*
C2	0.83507 (11)	0.2784 (3)	0.19184 (6)	0.0242 (4)
C3	0.92802 (12)	0.2308 (3)	0.18391 (6)	0.0256 (4)
C4	1.00681 (12)	0.3166 (3)	0.21709 (6)	0.0290 (4)
H4	1.0705	0.2860	0.2124	0.035*
C5	0.99712 (12)	0.4458 (3)	0.25699 (6)	0.0260 (4)
C6	0.90406 (12)	0.4902 (3)	0.26501 (6)	0.0236 (4)
C7	1.08897 (12)	0.5320 (4)	0.29004 (7)	0.0347 (5)
H7A	1.1317	0.5952	0.2697	0.042*
H7B	1.1240	0.4064	0.3087	0.042*
C8	1.07019 (12)	0.7074 (3)	0.32569 (6)	0.0311 (4)
H8A	1.0558	0.8511	0.3087	0.037*
H8B	1.1287	0.7259	0.3522	0.037*
C9	0.98365 (11)	0.6354 (3)	0.34705 (6)	0.0247 (4)
H9	0.9956	0.4752	0.3552	0.030*
C10	0.88796 (12)	0.6391 (3)	0.30715 (6)	0.0244 (4)
C11	0.97998 (13)	0.7481 (3)	0.39636 (6)	0.0273 (4)
C12	0.89331 (12)	0.6494 (3)	0.41521 (6)	0.0322 (4)
H12A	0.9076	0.4928	0.4245	0.039*
H12B	0.8859	0.7310	0.4448	0.039*
C13	0.79816 (13)	0.6614 (3)	0.37737 (7)	0.0337 (4)
H13A	0.7805	0.8186	0.3703	0.040*
H13B	0.7458	0.5917	0.3908	0.040*
C14	0.80555 (12)	0.5446 (3)	0.33004 (6)	0.0290 (4)
H14A	0.7427	0.5596	0.3063	0.035*
H14B	0.8174	0.3848	0.3367	0.035*
C15	0.74620 (12)	0.1981 (3)	0.15662 (7)	0.0283 (4)
C16	0.71899 (12)	0.3152 (3)	0.10892 (6)	0.0309 (4)
C17	0.65451 (13)	0.2155 (4)	0.06991 (7)	0.0438 (5)
H17	0.6272	0.0743	0.0737	0.053*
C18	0.63088 (15)	0.3267 (5)	0.02535 (7)	0.0577 (7)
H18	0.5882	0.2591	−0.0016	0.069*
C19	0.66864 (17)	0.5331 (5)	0.01990 (8)	0.0598 (7)
H19	0.6516	0.6070	−0.0106	0.072*
C20	0.73065 (16)	0.6326 (4)	0.05829 (8)	0.0519 (6)
H20	0.7560	0.7760	0.0546	0.062*
C21	0.75611 (14)	0.5227 (4)	0.10242 (7)	0.0385 (5)
H21	0.8000	0.5910	0.1288	0.046*
C22	0.94274 (12)	0.0864 (3)	0.14177 (7)	0.0313 (4)
H22	0.8769	0.0475	0.1220	0.038*
C23	0.99382 (16)	−0.1291 (4)	0.16058 (8)	0.0478 (5)
H23A	1.0590	−0.0961	0.1799	0.072*
H23B	0.9992	−0.2236	0.1329	0.072*
H23C	0.9560	−0.2061	0.1811	0.072*
C24	0.99781 (15)	0.2084 (4)	0.10829 (7)	0.0420 (5)
H24A	0.9609	0.3400	0.0947	0.063*
H24B	1.0058	0.1100	0.0816	0.063*
H24C	1.0620	0.2533	0.1270	0.063*
C25	0.85694 (14)	0.8673 (3)	0.28468 (7)	0.0322 (4)
H25A	0.9122	0.9375	0.2745	0.048*
H25B	0.8356	0.9608	0.3089	0.048*
H25C	0.8032	0.8489	0.2562	0.048*
C26	1.07336 (13)	0.6868 (3)	0.43273 (6)	0.0291 (4)
C27	1.17398 (15)	0.3934 (4)	0.46981 (7)	0.0423 (5)
H27A	1.2312	0.4530	0.4595	0.063*
H27B	1.1763	0.2312	0.4695	0.063*
H27C	1.1736	0.4452	0.5029	0.063*
C28	0.97432 (15)	1.0009 (3)	0.39479 (8)	0.0386 (5)
H28A	0.9102	1.0467	0.3762	0.058*
H28B	1.0249	1.0592	0.3790	0.058*
H28C	0.9843	1.0589	0.4281	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0356 (7)	0.0483 (9)	0.0503 (9)	−0.0140 (7)	0.0034 (6)	0.0026 (8)
O2	0.0512 (9)	0.0343 (8)	0.0602 (10)	−0.0028 (8)	−0.0224 (8)	−0.0054 (7)
O3	0.0397 (8)	0.0273 (7)	0.0484 (8)	0.0060 (6)	−0.0161 (6)	−0.0040 (6)
C1	0.0193 (8)	0.0283 (10)	0.0273 (9)	0.0015 (7)	0.0067 (7)	0.0000 (8)
C2	0.0207 (8)	0.0259 (10)	0.0250 (9)	0.0004 (7)	0.0030 (7)	0.0029 (8)
C3	0.0238 (9)	0.0261 (9)	0.0263 (9)	−0.0009 (8)	0.0044 (7)	0.0009 (8)
C4	0.0214 (9)	0.0357 (11)	0.0306 (9)	0.0028 (8)	0.0073 (8)	−0.0002 (8)
C5	0.0219 (9)	0.0306 (11)	0.0250 (9)	−0.0004 (8)	0.0042 (7)	0.0021 (8)
C6	0.0223 (8)	0.0246 (9)	0.0226 (9)	0.0005 (7)	0.0018 (7)	0.0026 (7)
C7	0.0216 (9)	0.0500 (13)	0.0312 (10)	−0.0020 (10)	0.0033 (7)	−0.0038 (10)
C8	0.0237 (9)	0.0365 (11)	0.0309 (10)	−0.0060 (9)	0.0006 (7)	0.0009 (9)
C9	0.0231 (9)	0.0238 (9)	0.0257 (9)	0.0001 (7)	0.0020 (7)	−0.0011 (7)
C10	0.0216 (9)	0.0249 (9)	0.0255 (9)	0.0016 (7)	0.0024 (7)	0.0003 (7)
C11	0.0278 (9)	0.0238 (9)	0.0287 (9)	0.0009 (8)	0.0025 (7)	−0.0014 (8)
C12	0.0327 (10)	0.0363 (11)	0.0278 (10)	0.0018 (9)	0.0072 (8)	−0.0037 (9)
C13	0.0287 (9)	0.0400 (12)	0.0325 (10)	0.0013 (9)	0.0069 (8)	−0.0039 (9)
C14	0.0224 (8)	0.0344 (10)	0.0303 (10)	−0.0006 (8)	0.0056 (7)	−0.0025 (9)
C15	0.0222 (9)	0.0302 (10)	0.0331 (10)	−0.0008 (9)	0.0074 (7)	−0.0060 (8)
C16	0.0210 (9)	0.0443 (12)	0.0267 (9)	0.0049 (9)	0.0036 (7)	−0.0032 (9)
C17	0.0245 (9)	0.0699 (15)	0.0369 (11)	0.0012 (10)	0.0061 (8)	−0.0144 (11)
C18	0.0333 (11)	0.110 (2)	0.0261 (11)	0.0124 (15)	−0.0014 (9)	−0.0142 (13)
C19	0.0480 (14)	0.096 (2)	0.0376 (13)	0.0229 (16)	0.0130 (11)	0.0138 (15)
C20	0.0527 (13)	0.0612 (15)	0.0444 (13)	0.0138 (12)	0.0161 (11)	0.0148 (12)
C21	0.0354 (10)	0.0462 (13)	0.0333 (11)	0.0072 (10)	0.0062 (8)	0.0035 (10)
C22	0.0249 (9)	0.0361 (11)	0.0330 (10)	0.0005 (9)	0.0065 (8)	−0.0064 (9)
C23	0.0533 (13)	0.0383 (12)	0.0543 (13)	0.0093 (11)	0.0172 (11)	−0.0064 (11)
C24	0.0457 (11)	0.0498 (13)	0.0334 (11)	−0.0029 (11)	0.0155 (9)	−0.0071 (10)
C25	0.0340 (10)	0.0279 (10)	0.0320 (10)	0.0032 (9)	0.0011 (8)	0.0012 (8)
C26	0.0318 (10)	0.0281 (10)	0.0257 (9)	−0.0004 (9)	0.0023 (8)	−0.0029 (8)
C27	0.0422 (12)	0.0421 (12)	0.0359 (11)	0.0150 (10)	−0.0061 (9)	−0.0013 (10)
C28	0.0432 (11)	0.0268 (10)	0.0410 (12)	0.0014 (9)	−0.0015 (9)	−0.0051 (9)

Geometric parameters (Å, º)

O1—C15	1.217 (2)	C13—H13A	0.9900
O2—C26	1.197 (2)	C13—H13B	0.9900
O3—C26	1.334 (2)	C14—H14A	0.9900
O3—C27	1.441 (2)	C14—H14B	0.9900
C1—C2	1.385 (2)	C15—C16	1.489 (3)
C1—C6	1.394 (2)	C16—C21	1.384 (3)
C1—H1	0.9500	C16—C17	1.399 (3)
C2—C3	1.402 (2)	C17—C18	1.395 (3)
C2—C15	1.497 (2)	C17—H17	0.9500
C3—C4	1.385 (2)	C18—C19	1.375 (4)
C3—C22	1.518 (2)	C18—H18	0.9500
C4—C5	1.395 (2)	C19—C20	1.370 (3)
C4—H4	0.9500	C19—H19	0.9500
C5—C6	1.400 (2)	C20—C21	1.382 (3)
C5—C7	1.511 (2)	C20—H20	0.9500
C6—C10	1.540 (2)	C21—H21	0.9500
C7—C8	1.518 (3)	C22—C23	1.525 (3)
C7—H7A	0.9900	C22—C24	1.528 (3)
C7—H7B	0.9900	C22—H22	1.0000
C8—C9	1.530 (2)	C23—H23A	0.9800
C8—H8A	0.9900	C23—H23B	0.9800
C8—H8B	0.9900	C23—H23C	0.9800
C9—C11	1.552 (2)	C24—H24A	0.9800
C9—C10	1.555 (2)	C24—H24B	0.9800
C9—H9	1.0000	C24—H24C	0.9800
C10—C25	1.539 (2)	C25—H25A	0.9800
C10—C14	1.549 (2)	C25—H25B	0.9800
C11—C26	1.525 (2)	C25—H25C	0.9800
C11—C28	1.528 (3)	C27—H27A	0.9800
C11—C12	1.548 (3)	C27—H27B	0.9800
C12—C13	1.520 (2)	C27—H27C	0.9800
C12—H12A	0.9900	C28—H28A	0.9800
C12—H12B	0.9900	C28—H28B	0.9800
C13—C14	1.526 (3)	C28—H28C	0.9800
C26—O3—C27	116.78 (15)	C13—C14—H14B	109.0
C2—C1—C6	122.53 (15)	C10—C14—H14B	109.0
C2—C1—H1	118.7	H14A—C14—H14B	107.8
C6—C1—H1	118.7	O1—C15—C16	121.21 (16)
C1—C2—C3	120.27 (15)	O1—C15—C2	121.66 (16)
C1—C2—C15	119.50 (15)	C16—C15—C2	117.13 (15)
C3—C2—C15	120.22 (15)	C21—C16—C17	119.08 (19)
C4—C3—C2	117.08 (15)	C21—C16—C15	121.12 (17)
C4—C3—C22	120.97 (15)	C17—C16—C15	119.80 (18)
C2—C3—C22	121.93 (15)	C18—C17—C16	118.9 (2)
C3—C4—C5	123.11 (15)	C18—C17—H17	120.5
C3—C4—H4	118.4	C16—C17—H17	120.5
C5—C4—H4	118.4	C19—C18—C17	120.8 (2)
C4—C5—C6	119.45 (15)	C19—C18—H18	119.6
C4—C5—C7	117.83 (15)	C17—C18—H18	119.6
C6—C5—C7	122.71 (16)	C20—C19—C18	120.4 (2)
C1—C6—C5	117.54 (16)	C20—C19—H19	119.8
C1—C6—C10	120.27 (15)	C18—C19—H19	119.8
C5—C6—C10	122.11 (15)	C19—C20—C21	119.5 (2)
C5—C7—C8	113.43 (14)	C19—C20—H20	120.3
C5—C7—H7A	108.9	C21—C20—H20	120.3
C8—C7—H7A	108.9	C20—C21—C16	121.3 (2)
C5—C7—H7B	108.9	C20—C21—H21	119.3
C8—C7—H7B	108.9	C16—C21—H21	119.3
H7A—C7—H7B	107.7	C3—C22—C23	110.68 (16)
C7—C8—C9	108.99 (15)	C3—C22—C24	111.96 (16)
C7—C8—H8A	109.9	C23—C22—C24	111.12 (16)
C9—C8—H8A	109.9	C3—C22—H22	107.6
C7—C8—H8B	109.9	C23—C22—H22	107.6
C9—C8—H8B	109.9	C24—C22—H22	107.6
H8A—C8—H8B	108.3	C22—C23—H23A	109.5
C8—C9—C11	113.94 (14)	C22—C23—H23B	109.5
C8—C9—C10	110.63 (13)	H23A—C23—H23B	109.5
C11—C9—C10	116.49 (13)	C22—C23—H23C	109.5
C8—C9—H9	104.8	H23A—C23—H23C	109.5
C11—C9—H9	104.8	H23B—C23—H23C	109.5
C10—C9—H9	104.8	C22—C24—H24A	109.5
C25—C10—C6	106.47 (14)	C22—C24—H24B	109.5
C25—C10—C14	109.13 (14)	H24A—C24—H24B	109.5
C6—C10—C14	110.48 (14)	C22—C24—H24C	109.5
C25—C10—C9	115.66 (14)	H24A—C24—H24C	109.5
C6—C10—C9	107.29 (13)	H24B—C24—H24C	109.5
C14—C10—C9	107.77 (13)	C10—C25—H25A	109.5
C26—C11—C28	107.08 (15)	C10—C25—H25B	109.5
C26—C11—C12	107.81 (14)	H25A—C25—H25B	109.5
C28—C11—C12	110.75 (16)	C10—C25—H25C	109.5
C26—C11—C9	107.52 (14)	H25A—C25—H25C	109.5
C28—C11—C9	115.05 (16)	H25B—C25—H25C	109.5
C12—C11—C9	108.35 (14)	O2—C26—O3	121.67 (17)
C13—C12—C11	112.50 (14)	O2—C26—C11	125.81 (17)
C13—C12—H12A	109.1	O3—C26—C11	112.52 (15)
C11—C12—H12A	109.1	O3—C27—H27A	109.5
C13—C12—H12B	109.1	O3—C27—H27B	109.5
C11—C12—H12B	109.1	H27A—C27—H27B	109.5
H12A—C12—H12B	107.8	O3—C27—H27C	109.5
C12—C13—C14	111.79 (14)	H27A—C27—H27C	109.5
C12—C13—H13A	109.3	H27B—C27—H27C	109.5
C14—C13—H13A	109.3	C11—C28—H28A	109.5
C12—C13—H13B	109.3	C11—C28—H28B	109.5
C14—C13—H13B	109.3	H28A—C28—H28B	109.5
H13A—C13—H13B	107.9	C11—C28—H28C	109.5
C13—C14—C10	112.80 (15)	H28A—C28—H28C	109.5
C13—C14—H14A	109.0	H28B—C28—H28C	109.5
C10—C14—H14A	109.0
C6—C1—C2—C3	0.9 (3)	C10—C9—C11—C12	52.91 (19)
C6—C1—C2—C15	−177.76 (16)	C26—C11—C12—C13	−168.98 (15)
C1—C2—C3—C4	−0.8 (2)	C28—C11—C12—C13	74.2 (2)
C15—C2—C3—C4	177.90 (16)	C9—C11—C12—C13	−52.9 (2)
C1—C2—C3—C22	177.54 (16)	C11—C12—C13—C14	57.0 (2)
C15—C2—C3—C22	−3.8 (3)	C12—C13—C14—C10	−57.4 (2)
C2—C3—C4—C5	−0.2 (3)	C25—C10—C14—C13	−73.31 (18)
C22—C3—C4—C5	−178.52 (17)	C6—C10—C14—C13	169.95 (14)
C3—C4—C5—C6	1.0 (3)	C9—C10—C14—C13	53.03 (19)
C3—C4—C5—C7	−179.16 (17)	C1—C2—C15—O1	−75.2 (2)
C2—C1—C6—C5	−0.1 (3)	C3—C2—C15—O1	106.1 (2)
C2—C1—C6—C10	176.66 (16)	C1—C2—C15—C16	104.27 (19)
C4—C5—C6—C1	−0.9 (2)	C3—C2—C15—C16	−74.4 (2)
C7—C5—C6—C1	179.33 (17)	O1—C15—C16—C21	162.02 (17)
C4—C5—C6—C10	−177.55 (16)	C2—C15—C16—C21	−17.5 (2)
C7—C5—C6—C10	2.6 (3)	O1—C15—C16—C17	−17.7 (3)
C4—C5—C7—C8	168.09 (16)	C2—C15—C16—C17	162.84 (16)
C6—C5—C7—C8	−12.1 (3)	C21—C16—C17—C18	1.1 (3)
C5—C7—C8—C9	43.1 (2)	C15—C16—C17—C18	−179.20 (18)
C7—C8—C9—C11	158.58 (15)	C16—C17—C18—C19	−1.3 (3)
C7—C8—C9—C10	−67.90 (18)	C17—C18—C19—C20	0.3 (3)
C1—C6—C10—C25	−76.17 (19)	C18—C19—C20—C21	0.9 (3)
C5—C6—C10—C25	100.43 (18)	C19—C20—C21—C16	−1.0 (3)
C1—C6—C10—C14	42.2 (2)	C17—C16—C21—C20	0.1 (3)
C5—C6—C10—C14	−141.19 (16)	C15—C16—C21—C20	−179.65 (17)
C1—C6—C10—C9	159.43 (15)	C4—C3—C22—C23	64.6 (2)
C5—C6—C10—C9	−24.0 (2)	C2—C3—C22—C23	−113.71 (19)
C8—C9—C10—C25	−62.64 (19)	C4—C3—C22—C24	−60.0 (2)
C11—C9—C10—C25	69.59 (19)	C2—C3—C22—C24	121.71 (18)
C8—C9—C10—C6	55.98 (18)	C27—O3—C26—O2	−0.3 (3)
C11—C9—C10—C6	−171.79 (14)	C27—O3—C26—C11	179.24 (15)
C8—C9—C10—C14	174.96 (15)	C28—C11—C26—O2	0.4 (3)
C11—C9—C10—C14	−52.81 (19)	C12—C11—C26—O2	−118.8 (2)
C8—C9—C11—C26	−60.12 (19)	C9—C11—C26—O2	124.5 (2)
C10—C9—C11—C26	169.19 (14)	C28—C11—C26—O3	−179.14 (17)
C8—C9—C11—C28	59.1 (2)	C12—C11—C26—O3	61.6 (2)
C10—C9—C11—C28	−71.6 (2)	C9—C11—C26—O3	−55.0 (2)
C8—C9—C11—C12	−176.39 (15)