13-Ethoxy-carbonyl-16-(1-methyl-ethyl)-17,19-dinoratis-15-ene-4,14-dicarboxylic acid monohydrate: a new derivative of maleopimaric acid.

The title compound, C(26)H(38)O(6)·H(2)O, is a mono-ester of a derivative of maleopimaric acid, an abietic-type acid. The two fused and unbridged cyclo-hexane rings adopt approximate chair conformations while the three other three six-membered rings have boat conformations.

Related literature

Abietic type resin acid, the major component of gum rosin, is a high quality biomass resource for the development of new chiral drugs, see: McCoy (2000 ▶); Schweizer et al. (2003 ▶). For the use of abietic acid and its derivatives in the design and synthesis of industrially and physiologically important products, see: Savluchinske-Feio et al. (2007 ▶). For the structures of other maleopimaric acid derivatives, see: Li et al. (2005 ▶); Pan et al. (2006 ▶); Rao et al. (2006 ▶).

Experimental

Crystal data

C26H38O6·H2O

M = 464.58

Orthorhombic,

a = 7.3406 (14) Å

b = 17.901 (4) Å

c = 19.681 (4) Å

V = 2586.2 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 291 K

0.26 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.98, T max = 0.98

14084 measured reflections

2892 independent reflections

2318 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.113

S = 1.08

2892 reflections

303 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028141/bh2234sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028141/bh2234Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H38O6·H2O	Dx = 1.193 Mg m−3
Mr = 464.58	Melting point: 412 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2351 reflections
a = 7.3406 (14) Å	θ = 2.4–23.1°
b = 17.901 (4) Å	µ = 0.09 mm−1
c = 19.681 (4) Å	T = 291 K
V = 2586.2 (9) Å3	Aciculae, colorless
Z = 4	0.26 × 0.22 × 0.20 mm
F(000) = 1008

Bruker SMART APEX CCD diffractometer	2892 independent reflections
Radiation source: sealed tube	2318 reflections with I > 2σ(I)
graphite	Rint = 0.076
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→9
Tmin = 0.98, Tmax = 0.98	k = −21→22
14084 measured reflections	l = −11→24

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.04P)2 + 0.66P] where P = (Fo2 + 2Fc2)/3
2892 reflections	(Δ/σ)max < 0.001
303 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.22 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	0.1062 (5)	0.27241 (19)	0.17771 (18)	0.0339 (8)
C2	0.1205 (5)	0.18852 (19)	0.16317 (18)	0.0321 (8)
H2	0.0801	0.1643	0.2052	0.039*
C3	0.3180 (5)	0.1612 (2)	0.1530 (2)	0.0386 (9)
H3A	0.3605	0.1755	0.1082	0.046*
H3B	0.3968	0.1845	0.1864	0.046*
C4	0.3272 (5)	0.0766 (2)	0.1604 (2)	0.0377 (9)
H4A	0.3005	0.0636	0.2072	0.045*
H4B	0.4505	0.0603	0.1507	0.045*
C5	0.1958 (5)	0.03398 (19)	0.11385 (18)	0.0330 (8)
C6	0.1724 (6)	−0.0481 (2)	0.14105 (18)	0.0378 (9)
H6	0.1139	−0.0455	0.1858	0.045*
C7	0.0419 (5)	−0.0908 (2)	0.0922 (2)	0.0382 (9)
H7	−0.0692	−0.1011	0.1182	0.046*
C8	−0.0146 (5)	−0.0396 (2)	0.03338 (19)	0.0406 (9)
H8	−0.0907	−0.0669	0.0009	0.049*
C9	−0.1211 (5)	0.0256 (2)	0.06435 (19)	0.0416 (9)
H9A	−0.2277	0.0066	0.0878	0.050*
H9B	−0.1621	0.0587	0.0284	0.050*
C10	0.0003 (5)	0.07016 (19)	0.11538 (19)	0.0339 (8)
H10	−0.0491	0.0597	0.1607	0.041*
C11	−0.0061 (5)	0.1561 (2)	0.10698 (18)	0.0360 (8)
C12	−0.2015 (5)	0.1820 (2)	0.1218 (2)	0.0411 (9)
H12A	−0.2443	0.1576	0.1629	0.049*
H12B	−0.2799	0.1665	0.0848	0.049*
C13	−0.2173 (5)	0.2672 (2)	0.1309 (2)	0.0426 (9)
H13A	−0.1819	0.2918	0.0891	0.051*
H13B	−0.3430	0.2802	0.1404	0.051*
C14	−0.0966 (5)	0.2947 (2)	0.1888 (2)	0.0394 (9)
H14A	−0.1394	0.2737	0.2313	0.047*
H14B	−0.1057	0.3487	0.1919	0.047*
C15	0.1951 (6)	0.3238 (2)	0.1237 (2)	0.0407 (9)
H15A	0.2085	0.3732	0.1420	0.061*
H15B	0.1192	0.3256	0.0840	0.061*
H15C	0.3127	0.3045	0.1117	0.061*
C16	0.0475 (6)	0.1813 (2)	0.03444 (19)	0.0417 (9)
H16A	−0.0103	0.1494	0.0017	0.063*
H16B	0.1773	0.1782	0.0293	0.063*
H16C	0.0087	0.2319	0.0274	0.063*
C17	0.2593 (6)	0.0286 (2)	0.04130 (19)	0.0388 (9)
H17	0.3666	0.0512	0.0268	0.047*
C18	0.1540 (5)	−0.01020 (19)	−0.00112 (19)	0.0364 (8)
C19	0.1871 (5)	−0.0250 (2)	−0.07525 (19)	0.0433 (10)
H19	0.1618	−0.0780	−0.0832	0.052*
C20	0.0537 (6)	0.0199 (2)	−0.1194 (2)	0.0452 (10)
H20A	−0.0670	0.0156	−0.1010	0.068*
H20B	0.0552	0.0007	−0.1649	0.068*
H20C	0.0895	0.0715	−0.1197	0.068*
C21	0.3860 (6)	−0.0108 (2)	−0.0965 (2)	0.0467 (10)
H21A	0.4165	0.0406	−0.0883	0.070*
H21B	0.4001	−0.0217	−0.1440	0.070*
H21C	0.4654	−0.0424	−0.0706	0.070*
C22	0.1092 (6)	−0.1652 (2)	0.0662 (2)	0.0415 (9)
C23	0.2168 (6)	−0.2869 (2)	0.0970 (2)	0.0429 (9)
H23A	0.1186	−0.3141	0.0752	0.051*
H23B	0.3167	−0.2825	0.0650	0.051*
C24	0.2779 (6)	−0.3275 (2)	0.1586 (2)	0.0447 (10)
H24A	0.3775	−0.3011	0.1792	0.067*
H24B	0.3169	−0.3769	0.1462	0.067*
H24C	0.1789	−0.3309	0.1904	0.067*
C25	0.1958 (5)	0.2900 (2)	0.24603 (19)	0.0371 (8)
C26	0.3572 (5)	−0.0844 (2)	0.1500 (2)	0.0384 (9)
O1	0.2639 (4)	0.35119 (14)	0.25908 (13)	0.0424 (7)
H1B	0.3484	0.3602	0.2308	0.051*
O2	0.1860 (4)	0.23935 (14)	0.29190 (13)	0.0423 (7)
O3	0.4065 (4)	−0.09128 (14)	0.21215 (13)	0.0436 (7)
O4	0.4538 (4)	−0.10191 (15)	0.10165 (13)	0.0409 (6)
H4D	0.3978	−0.1341	0.0778	0.049*
O5	0.1529 (4)	−0.21151 (13)	0.11749 (13)	0.0391 (6)
O6	0.1159 (3)	−0.18329 (13)	0.00746 (14)	0.0408 (6)
O7	0.2953 (4)	0.28560 (15)	0.40900 (13)	0.0425 (6)
H7A	0.2924	0.3307	0.4224	0.051*
H7B	0.2238	0.2594	0.4333	0.051*

	U11	U22	U33	U12	U13	U23
C1	0.0347 (19)	0.0271 (17)	0.040 (2)	−0.0036 (16)	0.0019 (17)	−0.0020 (15)
C2	0.0265 (18)	0.0361 (19)	0.0337 (19)	−0.0052 (15)	−0.0003 (16)	−0.0016 (16)
C3	0.0275 (19)	0.040 (2)	0.048 (2)	0.0030 (16)	−0.0046 (18)	−0.0039 (17)
C4	0.0325 (19)	0.037 (2)	0.044 (2)	0.0000 (16)	−0.0080 (17)	−0.0032 (17)
C5	0.0271 (18)	0.0347 (19)	0.037 (2)	0.0018 (14)	0.0040 (16)	−0.0036 (16)
C6	0.048 (2)	0.038 (2)	0.0274 (19)	0.0047 (18)	0.0051 (17)	−0.0015 (15)
C7	0.035 (2)	0.0338 (19)	0.045 (2)	−0.0025 (16)	0.0062 (17)	−0.0028 (18)
C8	0.043 (2)	0.042 (2)	0.037 (2)	0.0004 (17)	−0.0015 (19)	−0.0089 (18)
C9	0.036 (2)	0.051 (2)	0.037 (2)	−0.0026 (18)	−0.0058 (18)	−0.0076 (18)
C10	0.0252 (17)	0.039 (2)	0.038 (2)	0.0000 (15)	0.0017 (17)	−0.0099 (16)
C11	0.0354 (19)	0.0377 (19)	0.035 (2)	−0.0004 (16)	0.0016 (18)	−0.0008 (16)
C12	0.0298 (19)	0.049 (2)	0.044 (2)	0.0025 (17)	−0.0049 (17)	−0.0099 (19)
C13	0.035 (2)	0.045 (2)	0.048 (2)	0.0020 (17)	−0.0037 (18)	−0.0020 (18)
C14	0.040 (2)	0.037 (2)	0.042 (2)	0.0057 (17)	0.0020 (18)	−0.0030 (17)
C15	0.041 (2)	0.039 (2)	0.042 (2)	−0.0034 (17)	0.0019 (18)	0.0011 (17)
C16	0.048 (2)	0.039 (2)	0.039 (2)	0.0049 (18)	−0.0066 (18)	0.0010 (17)
C17	0.041 (2)	0.036 (2)	0.040 (2)	0.0054 (17)	0.0039 (18)	−0.0010 (16)
C18	0.040 (2)	0.0335 (19)	0.0356 (19)	0.0076 (16)	−0.0004 (17)	0.0017 (17)
C19	0.042 (2)	0.053 (2)	0.035 (2)	0.0143 (19)	0.0014 (18)	0.0017 (18)
C20	0.047 (2)	0.046 (2)	0.043 (2)	0.0144 (18)	−0.0070 (19)	0.0063 (18)
C21	0.054 (3)	0.045 (2)	0.041 (2)	−0.0068 (19)	0.021 (2)	−0.0155 (19)
C22	0.048 (2)	0.032 (2)	0.044 (2)	−0.0064 (18)	0.005 (2)	−0.0064 (17)
C23	0.038 (2)	0.047 (2)	0.044 (2)	0.0031 (18)	0.0079 (19)	−0.0003 (19)
C24	0.042 (2)	0.046 (2)	0.046 (2)	0.0153 (19)	0.0146 (19)	0.0098 (18)
C25	0.038 (2)	0.037 (2)	0.0358 (19)	−0.0016 (17)	−0.0063 (17)	−0.0104 (17)
C26	0.045 (2)	0.0295 (19)	0.041 (2)	0.0031 (17)	0.0013 (18)	−0.0051 (16)
O1	0.0412 (15)	0.0444 (15)	0.0415 (15)	−0.0124 (13)	−0.0165 (13)	0.0077 (12)
O2	0.0409 (15)	0.0438 (15)	0.0423 (14)	−0.0094 (12)	−0.0090 (13)	0.0049 (12)
O3	0.0449 (16)	0.0410 (14)	0.0449 (16)	0.0214 (13)	−0.0168 (13)	−0.0026 (12)
O4	0.0414 (15)	0.0439 (16)	0.0375 (15)	0.0136 (12)	−0.0009 (12)	−0.0033 (12)
O5	0.0464 (15)	0.0319 (13)	0.0391 (14)	−0.0007 (12)	0.0035 (12)	−0.0011 (11)
O6	0.0421 (15)	0.0375 (14)	0.0429 (15)	0.0016 (12)	0.0042 (13)	−0.0123 (12)
O7	0.0413 (15)	0.0449 (15)	0.0413 (15)	−0.0066 (12)	−0.0096 (12)	0.0059 (13)

C1—C25	1.530 (5)	C14—H14A	0.9700
C1—C2	1.532 (5)	C14—H14B	0.9700
C1—C15	1.550 (5)	C15—H15A	0.9600
C1—C14	1.557 (5)	C15—H15B	0.9600
C2—C3	1.543 (5)	C15—H15C	0.9600
C2—C11	1.557 (5)	C16—H16A	0.9600
C2—H2	0.9800	C16—H16B	0.9600
C3—C4	1.523 (5)	C16—H16C	0.9600
C3—H3A	0.9700	C17—C18	1.333 (5)
C3—H3B	0.9700	C17—H17	0.9300
C4—C5	1.533 (5)	C18—C19	1.503 (5)
C4—H4A	0.9700	C19—C20	1.535 (5)
C4—H4B	0.9700	C19—C21	1.540 (6)
C5—C17	1.505 (5)	C19—H19	0.9800
C5—C6	1.574 (5)	C20—H20A	0.9600
C5—C10	1.574 (5)	C20—H20B	0.9600
C6—C26	1.514 (5)	C20—H20C	0.9600
C6—C7	1.557 (5)	C21—H21A	0.9600
C6—H6	0.9800	C21—H21B	0.9600
C7—C22	1.510 (5)	C21—H21C	0.9600
C7—C8	1.534 (5)	C22—O6	1.201 (4)
C7—H7	0.9800	C22—O5	1.345 (5)
C8—C18	1.506 (5)	C23—C24	1.484 (5)
C8—C9	1.532 (5)	C23—O5	1.484 (5)
C8—H8	0.9800	C23—H23A	0.9700
C9—C10	1.562 (5)	C23—H23B	0.9700
C9—H9A	0.9700	C24—H24A	0.9600
C9—H9B	0.9700	C24—H24B	0.9600
C10—C11	1.548 (5)	C24—H24C	0.9600
C10—H10	0.9800	C25—O1	1.231 (4)
C11—C12	1.535 (5)	C25—O2	1.281 (4)
C11—C16	1.548 (5)	C26—O4	1.227 (4)
C12—C13	1.539 (5)	C26—O3	1.282 (4)
C12—H12A	0.9700	O1—H1B	0.8499
C12—H12B	0.9700	O4—H4D	0.8500
C13—C14	1.524 (5)	O7—H7A	0.8499
C13—H13A	0.9700	O7—H7B	0.8501
C13—H13B	0.9700
C25—C1—C2	109.6 (3)	C14—C13—H13A	109.4
C25—C1—C15	107.4 (3)	C12—C13—H13A	109.4
C2—C1—C15	115.1 (3)	C14—C13—H13B	109.4
C25—C1—C14	103.6 (3)	C12—C13—H13B	109.4
C2—C1—C14	110.1 (3)	H13A—C13—H13B	108.0
C15—C1—C14	110.2 (3)	C13—C14—C1	111.6 (3)
C1—C2—C3	113.6 (3)	C13—C14—H14A	109.3
C1—C2—C11	117.2 (3)	C1—C14—H14A	109.3
C3—C2—C11	110.5 (3)	C13—C14—H14B	109.3
C1—C2—H2	104.7	C1—C14—H14B	109.3
C3—C2—H2	104.7	H14A—C14—H14B	108.0
C11—C2—H2	104.7	C1—C15—H15A	109.5
C4—C3—C2	110.1 (3)	C1—C15—H15B	109.5
C4—C3—H3A	109.6	H15A—C15—H15B	109.5
C2—C3—H3A	109.6	C1—C15—H15C	109.5
C4—C3—H3B	109.6	H15A—C15—H15C	109.5
C2—C3—H3B	109.6	H15B—C15—H15C	109.5
H3A—C3—H3B	108.1	C11—C16—H16A	109.5
C3—C4—C5	114.2 (3)	C11—C16—H16B	109.5
C3—C4—H4A	108.7	H16A—C16—H16B	109.5
C5—C4—H4A	108.7	C11—C16—H16C	109.5
C3—C4—H4B	108.7	H16A—C16—H16C	109.5
C5—C4—H4B	108.7	H16B—C16—H16C	109.5
H4A—C4—H4B	107.6	C18—C17—C5	116.6 (4)
C17—C5—C4	113.8 (3)	C18—C17—H17	121.7
C17—C5—C6	107.3 (3)	C5—C17—H17	121.7
C4—C5—C6	109.3 (3)	C17—C18—C19	127.3 (4)
C17—C5—C10	109.1 (3)	C17—C18—C8	112.1 (3)
C4—C5—C10	110.9 (3)	C19—C18—C8	120.6 (3)
C6—C5—C10	106.2 (3)	C18—C19—C20	110.7 (3)
C26—C6—C7	114.4 (3)	C18—C19—C21	112.9 (3)
C26—C6—C5	110.0 (3)	C20—C19—C21	111.4 (4)
C7—C6—C5	108.4 (3)	C18—C19—H19	107.2
C26—C6—H6	108.0	C20—C19—H19	107.2
C7—C6—H6	108.0	C21—C19—H19	107.2
C5—C6—H6	108.0	C19—C20—H20A	109.5
C22—C7—C8	111.1 (3)	C19—C20—H20B	109.5
C22—C7—C6	116.1 (3)	H20A—C20—H20B	109.5
C8—C7—C6	109.8 (3)	C19—C20—H20C	109.5
C22—C7—H7	106.4	H20A—C20—H20C	109.5
C8—C7—H7	106.4	H20B—C20—H20C	109.5
C6—C7—H7	106.4	C19—C21—H21A	109.5
C18—C8—C9	109.4 (3)	C19—C21—H21B	109.5
C18—C8—C7	109.1 (3)	H21A—C21—H21B	109.5
C9—C8—C7	107.0 (3)	C19—C21—H21C	109.5
C18—C8—H8	110.4	H21A—C21—H21C	109.5
C9—C8—H8	110.4	H21B—C21—H21C	109.5
C7—C8—H8	110.4	O6—C22—O5	123.1 (3)
C8—C9—C10	110.7 (3)	O6—C22—C7	125.3 (4)
C8—C9—H9A	109.5	O5—C22—C7	111.5 (3)
C10—C9—H9A	109.5	C24—C23—O5	108.6 (3)
C8—C9—H9B	109.5	C24—C23—H23A	110.0
C10—C9—H9B	109.5	O5—C23—H23A	110.0
H9A—C9—H9B	108.1	C24—C23—H23B	110.0
C11—C10—C9	114.9 (3)	O5—C23—H23B	110.0
C11—C10—C5	115.8 (3)	H23A—C23—H23B	108.3
C9—C10—C5	107.3 (3)	C23—C24—H24A	109.5
C11—C10—H10	106.0	C23—C24—H24B	109.5
C9—C10—H10	106.0	H24A—C24—H24B	109.5
C5—C10—H10	106.0	C23—C24—H24C	109.5
C12—C11—C16	109.0 (3)	H24A—C24—H24C	109.5
C12—C11—C10	107.9 (3)	H24B—C24—H24C	109.5
C16—C11—C10	112.3 (3)	O1—C25—O2	120.3 (3)
C12—C11—C2	108.1 (3)	O1—C25—C1	122.7 (3)
C16—C11—C2	113.3 (3)	O2—C25—C1	116.7 (3)
C10—C11—C2	106.0 (3)	O4—C26—O3	123.5 (4)
C11—C12—C13	113.0 (3)	O4—C26—C6	122.5 (4)
C11—C12—H12A	109.0	O3—C26—C6	113.9 (3)
C13—C12—H12A	109.0	C25—O1—H1B	109.1
C11—C12—H12B	109.0	C26—O4—H4D	108.8
C13—C12—H12B	109.0	C22—O5—C23	115.6 (3)
H12A—C12—H12B	107.8	H7A—O7—H7B	109.5
C14—C13—C12	111.3 (3)
C25—C1—C2—C3	−65.4 (4)	C3—C2—C11—C12	177.2 (3)
C15—C1—C2—C3	55.8 (4)	C1—C2—C11—C16	70.3 (4)
C14—C1—C2—C3	−178.8 (3)	C3—C2—C11—C16	−61.9 (4)
C25—C1—C2—C11	163.8 (3)	C1—C2—C11—C10	−166.1 (3)
C15—C1—C2—C11	−75.0 (4)	C3—C2—C11—C10	61.7 (4)
C14—C1—C2—C11	50.4 (4)	C16—C11—C12—C13	−70.6 (4)
C1—C2—C3—C4	162.8 (3)	C10—C11—C12—C13	167.2 (3)
C11—C2—C3—C4	−63.2 (4)	C2—C11—C12—C13	52.9 (4)
C2—C3—C4—C5	54.5 (4)	C11—C12—C13—C14	−58.7 (4)
C3—C4—C5—C17	77.7 (4)	C12—C13—C14—C1	56.6 (4)
C3—C4—C5—C6	−162.5 (3)	C25—C1—C14—C13	−168.7 (3)
C3—C4—C5—C10	−45.8 (4)	C2—C1—C14—C13	−51.5 (4)
C17—C5—C6—C26	70.7 (4)	C15—C1—C14—C13	76.6 (4)
C4—C5—C6—C26	−53.1 (4)	C4—C5—C17—C18	177.6 (3)
C10—C5—C6—C26	−172.8 (3)	C6—C5—C17—C18	56.6 (4)
C17—C5—C6—C7	−55.0 (4)	C10—C5—C17—C18	−57.9 (4)
C4—C5—C6—C7	−178.8 (3)	C5—C17—C18—C19	−179.1 (3)
C10—C5—C6—C7	61.5 (4)	C5—C17—C18—C8	1.6 (5)
C26—C6—C7—C22	5.7 (5)	C9—C8—C18—C17	57.1 (4)
C5—C6—C7—C22	128.8 (3)	C7—C8—C18—C17	−59.7 (4)
C26—C6—C7—C8	−121.4 (3)	C9—C8—C18—C19	−122.3 (4)
C5—C6—C7—C8	1.8 (4)	C7—C8—C18—C19	120.9 (3)
C22—C7—C8—C18	−74.8 (4)	C17—C18—C19—C20	−108.6 (4)
C6—C7—C8—C18	55.0 (4)	C8—C18—C19—C20	70.7 (5)
C22—C7—C8—C9	166.9 (3)	C17—C18—C19—C21	17.0 (6)
C6—C7—C8—C9	−63.3 (4)	C8—C18—C19—C21	−163.7 (3)
C18—C8—C9—C10	−57.4 (4)	C8—C7—C22—O6	−1.2 (6)
C7—C8—C9—C10	60.7 (4)	C6—C7—C22—O6	−127.6 (4)
C8—C9—C10—C11	133.3 (3)	C8—C7—C22—O5	−177.8 (3)
C8—C9—C10—C5	3.0 (4)	C6—C7—C22—O5	55.8 (4)
C17—C5—C10—C11	−78.5 (4)	C2—C1—C25—O1	152.3 (4)
C4—C5—C10—C11	47.7 (4)	C15—C1—C25—O1	26.5 (5)
C6—C5—C10—C11	166.3 (3)	C14—C1—C25—O1	−90.2 (4)
C17—C5—C10—C9	51.4 (4)	C2—C1—C25—O2	−32.6 (4)
C4—C5—C10—C9	177.5 (3)	C15—C1—C25—O2	−158.4 (3)
C6—C5—C10—C9	−63.9 (4)	C14—C1—C25—O2	84.9 (4)
C9—C10—C11—C12	63.4 (4)	C7—C6—C26—O4	52.3 (5)
C5—C10—C11—C12	−170.5 (3)	C5—C6—C26—O4	−69.9 (4)
C9—C10—C11—C16	−56.8 (4)	C7—C6—C26—O3	−131.2 (3)
C5—C10—C11—C16	69.3 (4)	C5—C6—C26—O3	106.5 (4)
C9—C10—C11—C2	179.0 (3)	O6—C22—O5—C23	2.0 (5)
C5—C10—C11—C2	−54.9 (4)	C7—C22—O5—C23	178.7 (3)
C1—C2—C11—C12	−50.6 (4)	C24—C23—O5—C22	173.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4D···O5	0.85	2.40	2.971 (4)	125
O7—H7B···O6i	0.85	2.32	2.745 (4)	111
C2—H2···O2	0.98	2.31	2.735 (4)	105
C15—H15A···O1	0.96	2.37	2.756 (5)	103