(E)-Dimethyl 2-(6-benzoyl-7-hydr-oxy-4-methoxy-carbonyl-2-oxo-2H-chromen-8-yl)but-2-enedioate.

The mol-ecule of the title compound, C(24)H(18)O(10), a previously unknown coumarin derivative, contains methoxy-carbonyl, 2-butenedioate and benzoyl groups aligned at angles of 28.04 (2), 76.89 (3) and 42.48 (13)°, respectively, to the plane of the coumarin ring system. Intra-molecular O-H⋯O hydrogen bonding between hydr-oxy and carbonyl groups and weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure. The two carbon atoms and attached H atom of the ethylene bond are disordered over two positions, with site occupancy factors of ca 0.9 and 0.1.

Related literature

For general background, see: Maeda (1984 ▶); Parrish et al. (1974 ▶); Troste & Toste (1996 ▶); Khalfan et al. (1987 ▶); Hooper et al. (1982 ▶); Morris & Russell (1971 ▶).

Experimental

Crystal data

C24H18O10

M = 466.38

Orthorhombic,

a = 9.2661 (17) Å

b = 11.508 (2) Å

c = 19.661 (4) Å

V = 2096.5 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 120 (2) K

0.3 × 0.2 × 0.2 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.973, T max = 0.979

12547 measured reflections

2864 independent reflections

2194 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.113

S = 1.00

2864 reflections

323 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020990/xu2430sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020990/xu2430Isup2.hkl

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

C24H18O10	Dx = 1.478 Mg m−3
Mr = 466.38	Melting point: 457 K
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 557 reflections
a = 9.2661 (17) Å	θ = 3–28º
b = 11.508 (2) Å	µ = 0.12 mm−1
c = 19.661 (4) Å	T = 120 (2) K
V = 2096.5 (7) Å3	Rhombic, yellow
Z = 4	0.3 × 0.2 × 0.2 mm
F000 = 968

Bruker SMART 1000 CCD area-detector diffractometer	2864 independent reflections
Radiation source: fine-focus sealed tube	2194 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.046
T = 120(2) K	θmax = 28.0º
φ and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 2008)	h = −10→12
Tmin = 0.973, Tmax = 0.979	k = −15→13
12547 measured reflections	l = −17→25

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0236P)2 + 2.3937P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
2864 reflections	Δρmax = 0.35 e Å−3
323 parameters	Δρmin = −0.25 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Experimental. 1H NMR (500 MHz, CDCl3): δ = 3.66, 3.82 and 3.86 (9 H, 3 s, 3 OCH3), 6.82, 7.27 and 8.85 (3 H, 3 s, 3 CH), 7.54 -7.76 (5 H, m, CH, Aromatic), 12.90 (1 H, s, OH). 13C NMR (125.7 MHz, CDCl3): δ = 52.06, 53.11 and 53.18 (3 OCH3), 108.11 (CH), 112.32, 116.18, 117.22 (3 C), 128.58, 129.50, 132.13 and 132.74 (4 CH), 134.22, 135.26 and 137.06 (3 C), 141.60 (CH), 156.09 and 158.80 (2 C-O), 163.43, 163.87, 164.66 and 165.25 (4 C=O, Ester), 200.7 (C=O, Ketone). IR (KBr) (νmax /cm-1): 3320-3550 (OH), 1735-1750 (C=O, Ketone), 1615-1632 (C=O, Ester), 1400-1435 (C=C). MS, (m/z, %): 466 (9) (M+), 105 (25), 44 (98).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.8901 (3)	0.6309 (2)	0.47921 (12)	0.0296 (5)
O2	0.9133 (3)	0.7985 (2)	0.53324 (12)	0.0320 (6)
O3	0.8287 (3)	0.2634 (2)	0.38265 (14)	0.0382 (7)
O4	1.0075 (3)	0.4046 (3)	0.55108 (15)	0.0515 (8)
O5	0.8674 (3)	0.3474 (2)	0.63681 (14)	0.0394 (7)
O6	0.5738 (3)	0.4577 (3)	0.38390 (15)	0.0469 (7)
O7	0.4741 (3)	0.4059 (2)	0.48358 (14)	0.0395 (7)
O8	0.9960 (3)	0.2006 (2)	0.28708 (13)	0.0367 (6)
O9	1.3022 (3)	0.6689 (2)	0.30924 (13)	0.0331 (6)
O10	1.2205 (3)	0.8493 (2)	0.33093 (13)	0.0314 (6)
C1	0.9316 (4)	0.5539 (3)	0.42981 (17)	0.0265 (7)
C2	0.8588 (4)	0.4490 (3)	0.42914 (19)	0.0312 (8)
C3	0.8983 (4)	0.3662 (3)	0.38097 (19)	0.0294 (8)
C4	1.0067 (4)	0.3908 (3)	0.33190 (16)	0.0240 (7)
C5	1.0769 (4)	0.4973 (3)	0.33484 (16)	0.0241 (7)
H5A	1.1498	0.5131	0.3037	0.029*
C6	1.0414 (4)	0.5814 (3)	0.38323 (16)	0.0223 (6)
C7	1.1059 (4)	0.6962 (3)	0.38800 (16)	0.0244 (7)
C8	1.0624 (4)	0.7706 (3)	0.43690 (17)	0.0256 (7)
H8A	1.1037	0.8441	0.4389	0.031*
C9	0.9531 (4)	0.7394 (3)	0.48650 (17)	0.0263 (7)
C10	0.7329 (4)	0.4258 (3)	0.4747 (2)	0.0246 (8)	0.85
C11	0.7438 (4)	0.3982 (4)	0.5399 (2)	0.0285 (9)	0.85
H11A	0.6602	0.3865	0.5651	0.034*	0.85
C10'	0.817 (3)	0.4049 (19)	0.5058 (11)	0.022 (4)*	0.15
C11'	0.677 (3)	0.387 (2)	0.5078 (13)	0.038 (6)*	0.15
H11B	0.6332	0.3503	0.5446	0.045*	0.15
C12	0.8891 (5)	0.3854 (3)	0.5746 (2)	0.0380 (9)
C13	0.9957 (4)	0.3285 (4)	0.67707 (19)	0.0407 (10)
H13A	0.9693	0.2953	0.7201	0.061*
H13B	1.0439	0.4012	0.6844	0.061*
H13C	1.0591	0.2763	0.6535	0.061*
C14	0.5856 (4)	0.4312 (3)	0.4419 (2)	0.0363 (9)
C15	0.3335 (4)	0.4193 (4)	0.4522 (2)	0.0417 (10)
H15A	0.2605	0.3907	0.4825	0.063*
H15B	0.3306	0.3761	0.4105	0.063*
H15C	0.3164	0.5000	0.4429	0.063*
C16	1.0426 (4)	0.3018 (3)	0.28092 (18)	0.0273 (7)
C17	1.1342 (4)	0.3286 (3)	0.22093 (17)	0.0259 (7)
C18	1.2264 (4)	0.2416 (3)	0.19724 (18)	0.0297 (8)
H18A	1.2301	0.1703	0.2194	0.036*
C19	1.3132 (4)	0.2616 (3)	0.14031 (19)	0.0345 (9)
H19A	1.3768	0.2048	0.1251	0.041*
C20	1.3031 (4)	0.3672 (4)	0.1070 (2)	0.0372 (9)
H20A	1.3613	0.3813	0.0694	0.045*
C21	1.2084 (4)	0.4517 (3)	0.12855 (19)	0.0339 (8)
H21A	1.2013	0.5214	0.1048	0.041*
C22	1.1240 (4)	0.4333 (3)	0.18531 (18)	0.0291 (7)
H22A	1.0603	0.4906	0.1999	0.035*
C23	1.2213 (4)	0.7331 (3)	0.33863 (17)	0.0266 (7)
C24	1.3248 (4)	0.8940 (3)	0.2829 (2)	0.0361 (9)
H24A	1.3133	0.9766	0.2788	0.054*
H24B	1.3098	0.8582	0.2393	0.054*
H24C	1.4205	0.8769	0.2986	0.054*
H3O	0.884 (6)	0.213 (5)	0.352 (3)	0.078 (17)*

	U11	U22	U33	U12	U13	U23
O1	0.0358 (13)	0.0261 (12)	0.0269 (12)	−0.0040 (11)	0.0063 (11)	−0.0025 (10)
O2	0.0351 (14)	0.0322 (13)	0.0289 (13)	0.0018 (11)	0.0021 (11)	−0.0061 (11)
O3	0.0440 (16)	0.0275 (14)	0.0432 (16)	−0.0110 (12)	0.0143 (13)	−0.0061 (12)
O4	0.0523 (19)	0.065 (2)	0.0368 (16)	−0.0114 (17)	−0.0002 (15)	0.0119 (15)
O5	0.0301 (14)	0.0448 (16)	0.0433 (16)	0.0018 (12)	−0.0013 (13)	0.0071 (13)
O6	0.0376 (16)	0.0583 (19)	0.0447 (17)	−0.0016 (14)	0.0041 (14)	−0.0037 (15)
O7	0.0371 (15)	0.0433 (15)	0.0380 (15)	0.0026 (13)	−0.0069 (13)	0.0006 (13)
O8	0.0442 (16)	0.0248 (13)	0.0410 (15)	−0.0064 (12)	0.0104 (13)	−0.0035 (12)
O9	0.0299 (13)	0.0286 (13)	0.0408 (14)	−0.0029 (11)	0.0088 (12)	−0.0057 (12)
O10	0.0309 (13)	0.0264 (13)	0.0369 (14)	−0.0033 (11)	0.0065 (11)	0.0015 (11)
C1	0.0321 (18)	0.0248 (16)	0.0224 (16)	0.0022 (14)	−0.0005 (15)	0.0005 (14)
C2	0.038 (2)	0.0260 (17)	0.0302 (18)	−0.0046 (15)	0.0069 (16)	−0.0010 (15)
C3	0.0318 (18)	0.0239 (17)	0.0327 (18)	−0.0042 (14)	0.0020 (16)	0.0000 (15)
C4	0.0245 (16)	0.0249 (16)	0.0226 (16)	0.0005 (13)	−0.0012 (14)	−0.0015 (14)
C5	0.0246 (16)	0.0242 (16)	0.0236 (16)	0.0009 (13)	0.0001 (14)	0.0010 (14)
C6	0.0236 (15)	0.0218 (15)	0.0214 (15)	−0.0005 (13)	−0.0001 (13)	0.0000 (13)
C7	0.0247 (16)	0.0251 (16)	0.0233 (16)	0.0002 (14)	−0.0024 (14)	0.0011 (14)
C8	0.0266 (17)	0.0236 (16)	0.0266 (16)	−0.0006 (13)	−0.0024 (14)	−0.0009 (13)
C9	0.0286 (18)	0.0240 (16)	0.0263 (17)	0.0009 (14)	−0.0032 (14)	−0.0028 (15)
C10	0.0219 (19)	0.026 (2)	0.026 (2)	−0.0021 (16)	0.0013 (17)	0.0009 (17)
C11	0.025 (2)	0.029 (2)	0.031 (2)	0.0008 (17)	0.0036 (19)	0.0006 (18)
C12	0.043 (2)	0.0306 (19)	0.040 (2)	−0.0043 (18)	−0.0105 (19)	0.0019 (17)
C13	0.036 (2)	0.056 (3)	0.0305 (19)	0.0127 (19)	−0.0005 (17)	0.0111 (19)
C14	0.0253 (18)	0.032 (2)	0.052 (3)	0.0042 (16)	−0.0086 (18)	−0.0091 (18)
C15	0.0271 (19)	0.044 (2)	0.054 (3)	−0.0002 (17)	0.0013 (18)	−0.010 (2)
C16	0.0271 (17)	0.0235 (16)	0.0312 (18)	−0.0002 (14)	−0.0027 (15)	−0.0012 (15)
C17	0.0247 (16)	0.0266 (17)	0.0266 (17)	−0.0026 (14)	−0.0010 (14)	−0.0038 (14)
C18	0.0290 (18)	0.0263 (18)	0.0337 (19)	0.0003 (14)	−0.0036 (15)	−0.0058 (15)
C19	0.0294 (19)	0.036 (2)	0.038 (2)	0.0023 (16)	0.0009 (17)	−0.0102 (17)
C20	0.036 (2)	0.042 (2)	0.033 (2)	−0.0043 (17)	0.0085 (17)	−0.0090 (17)
C21	0.041 (2)	0.0302 (18)	0.0305 (18)	−0.0032 (16)	0.0022 (17)	−0.0036 (16)
C22	0.0325 (18)	0.0254 (17)	0.0294 (17)	0.0007 (15)	−0.0023 (16)	−0.0040 (15)
C23	0.0269 (17)	0.0260 (17)	0.0269 (17)	−0.0043 (14)	−0.0032 (15)	−0.0011 (15)
C24	0.036 (2)	0.0304 (19)	0.042 (2)	−0.0081 (17)	0.0083 (17)	0.0046 (17)

O1—C1	1.370 (4)	C10—C11	1.326 (6)
O1—C9	1.386 (4)	C10—C14	1.511 (5)
O2—C9	1.201 (4)	C11—C12	1.516 (6)
O3—C3	1.347 (4)	C11—H11A	0.9300
O3—H3O	0.99 (5)	C10'—C11'	1.31 (4)
O4—C12	1.211 (5)	C10'—C12	1.52 (2)
O5—C12	1.314 (5)	C11'—C14	1.63 (2)
O5—C13	1.444 (4)	C11'—H11B	0.9300
O6—C14	1.185 (5)	C13—H13A	0.9600
O7—C14	1.351 (5)	C13—H13B	0.9600
O7—C15	1.449 (5)	C13—H13C	0.9600
O8—C16	1.248 (4)	C15—H15A	0.9600
O9—C23	1.200 (4)	C15—H15B	0.9600
O10—C23	1.345 (4)	C15—H15C	0.9600
O10—C24	1.446 (4)	C16—C17	1.485 (5)
C1—C2	1.382 (5)	C17—C18	1.396 (5)
C1—C6	1.405 (5)	C17—C22	1.397 (5)
C2—C3	1.393 (5)	C18—C19	1.397 (5)
C2—C10	1.495 (5)	C18—H18A	0.9300
C2—C10'	1.64 (2)	C19—C20	1.383 (6)
C3—C4	1.421 (5)	C19—H19A	0.9300
C4—C5	1.389 (4)	C20—C21	1.377 (5)
C4—C16	1.471 (5)	C20—H20A	0.9300
C5—C6	1.396 (4)	C21—C22	1.379 (5)
C5—H5A	0.9300	C21—H21A	0.9300
C6—C7	1.454 (4)	C22—H22A	0.9300
C7—C8	1.349 (5)	C24—H24A	0.9600
C7—C23	1.505 (5)	C24—H24B	0.9600
C8—C9	1.451 (5)	C24—H24C	0.9600
C8—H8A	0.9300
C1—O1—C9	122.6 (3)	O4—C12—C10'	91.8 (9)
C3—O3—H3O	104 (3)	O5—C12—C10'	143.9 (10)
C12—O5—C13	115.7 (3)	O5—C13—H13A	109.5
C14—O7—C15	114.0 (3)	O5—C13—H13B	109.5
C23—O10—C24	115.1 (3)	H13A—C13—H13B	109.5
O1—C1—C2	115.8 (3)	O5—C13—H13C	109.5
O1—C1—C6	121.3 (3)	H13A—C13—H13C	109.5
C2—C1—C6	122.9 (3)	H13B—C13—H13C	109.5
C1—C2—C3	118.4 (3)	O6—C14—O7	124.7 (4)
C1—C2—C10	122.1 (3)	O6—C14—C10	120.3 (4)
C3—C2—C10	119.3 (3)	O7—C14—C10	115.0 (3)
C1—C2—C10'	112.2 (8)	O6—C14—C11'	153.2 (11)
C3—C2—C10'	118.4 (8)	O7—C14—C11'	81.3 (11)
O3—C3—C2	117.3 (3)	O7—C15—H15A	109.5
O3—C3—C4	122.0 (3)	O7—C15—H15B	109.5
C2—C3—C4	120.7 (3)	H15A—C15—H15B	109.5
C5—C4—C3	118.6 (3)	O7—C15—H15C	109.5
C5—C4—C16	122.4 (3)	H15A—C15—H15C	109.5
C3—C4—C16	118.9 (3)	H15B—C15—H15C	109.5
C4—C5—C6	121.9 (3)	O8—C16—C4	120.3 (3)
C4—C5—H5A	119.0	O8—C16—C17	117.9 (3)
C6—C5—H5A	119.0	C4—C16—C17	121.7 (3)
C5—C6—C1	117.3 (3)	C18—C17—C22	119.5 (3)
C5—C6—C7	125.2 (3)	C18—C17—C16	117.8 (3)
C1—C6—C7	117.4 (3)	C22—C17—C16	122.6 (3)
C8—C7—C6	120.0 (3)	C17—C18—C19	120.1 (3)
C8—C7—C23	119.6 (3)	C17—C18—H18A	119.9
C6—C7—C23	120.5 (3)	C19—C18—H18A	119.9
C7—C8—C9	122.1 (3)	C20—C19—C18	119.0 (3)
C7—C8—H8A	118.9	C20—C19—H19A	120.5
C9—C8—H8A	118.9	C18—C19—H19A	120.5
O2—C9—O1	117.4 (3)	C21—C20—C19	121.2 (4)
O2—C9—C8	126.0 (3)	C21—C20—H20A	119.4
O1—C9—C8	116.6 (3)	C19—C20—H20A	119.4
C11—C10—C2	124.3 (4)	C20—C21—C22	120.1 (4)
C11—C10—C14	119.5 (4)	C20—C21—H21A	119.9
C2—C10—C14	116.2 (3)	C22—C21—H21A	119.9
C10—C11—C12	121.7 (4)	C21—C22—C17	120.0 (3)
C10—C11—H11A	119.1	C21—C22—H22A	120.0
C12—C11—H11A	119.1	C17—C22—H22A	120.0
C11'—C10'—C12	112 (2)	O9—C23—O10	124.1 (3)
C11'—C10'—C2	108.1 (19)	O9—C23—C7	125.5 (3)
C12—C10'—C2	139.4 (16)	O10—C23—C7	110.4 (3)
C10'—C11'—C14	116 (2)	O10—C24—H24A	109.5
C10'—C11'—H11B	122.0	O10—C24—H24B	109.5
C14—C11'—H11B	122.0	H24A—C24—H24B	109.5
O4—C12—O5	123.7 (4)	O10—C24—H24C	109.5
O4—C12—C11	128.0 (4)	H24A—C24—H24C	109.5
O5—C12—C11	108.4 (4)	H24B—C24—H24C	109.5
C9—O1—C1—C2	179.8 (3)	C10—C2—C10'—C12	−165 (3)
C9—O1—C1—C6	−0.2 (5)	C12—C10'—C11'—C14	167.5 (15)
O1—C1—C2—C3	−178.7 (3)	C2—C10'—C11'—C14	−10 (3)
C6—C1—C2—C3	1.3 (5)	C13—O5—C12—O4	−0.4 (6)
O1—C1—C2—C10	6.0 (5)	C13—O5—C12—C11	179.1 (3)
C6—C1—C2—C10	−174.0 (3)	C13—O5—C12—C10'	167.0 (15)
O1—C1—C2—C10'	−35.1 (10)	C10—C11—C12—O4	5.3 (7)
C6—C1—C2—C10'	144.9 (9)	C10—C11—C12—O5	−174.2 (4)
C1—C2—C3—O3	178.1 (3)	C10—C11—C12—C10'	−6.1 (14)
C10—C2—C3—O3	−6.5 (5)	C11'—C10'—C12—O4	177 (2)
C10'—C2—C3—O3	36.8 (10)	C2—C10'—C12—O4	−7(2)
C1—C2—C3—C4	−2.6 (5)	C11'—C10'—C12—O5	8(3)
C10—C2—C3—C4	172.9 (3)	C2—C10'—C12—O5	−176.5 (11)
C10'—C2—C3—C4	−143.9 (10)	C11'—C10'—C12—C11	−11.8 (15)
O3—C3—C4—C5	−177.9 (3)	C2—C10'—C12—C11	164 (3)
C2—C3—C4—C5	2.8 (5)	C15—O7—C14—O6	−2.9 (6)
O3—C3—C4—C16	0.7 (5)	C15—O7—C14—C10	176.0 (3)
C2—C3—C4—C16	−178.6 (3)	C15—O7—C14—C11'	−175.6 (11)
C3—C4—C5—C6	−1.8 (5)	C11—C10—C14—O6	178.6 (4)
C16—C4—C5—C6	179.7 (3)	C2—C10—C14—O6	−3.2 (6)
C4—C5—C6—C1	0.5 (5)	C11—C10—C14—O7	−0.3 (5)
C4—C5—C6—C7	−177.6 (3)	C2—C10—C14—O7	177.8 (3)
O1—C1—C6—C5	179.7 (3)	C11—C10—C14—C11'	−15.0 (18)
C2—C1—C6—C5	−0.3 (5)	C2—C10—C14—C11'	163.2 (18)
O1—C1—C6—C7	−2.0 (5)	C10'—C11'—C14—O6	24 (4)
C2—C1—C6—C7	178.0 (3)	C10'—C11'—C14—O7	−170 (2)
C5—C6—C7—C8	179.7 (3)	C10'—C11'—C14—C10	−3.2 (12)
C1—C6—C7—C8	1.6 (5)	C5—C4—C16—O8	167.3 (3)
C5—C6—C7—C23	−0.2 (5)	C3—C4—C16—O8	−11.2 (5)
C1—C6—C7—C23	−178.3 (3)	C5—C4—C16—C17	−12.8 (5)
C6—C7—C8—C9	0.9 (5)	C3—C4—C16—C17	168.6 (3)
C23—C7—C8—C9	−179.1 (3)	O8—C16—C17—C18	−34.7 (5)
C1—O1—C9—O2	−176.9 (3)	C4—C16—C17—C18	145.5 (3)
C1—O1—C9—C8	2.7 (5)	O8—C16—C17—C22	140.9 (4)
C7—C8—C9—O2	176.5 (3)	C4—C16—C17—C22	−38.9 (5)
C7—C8—C9—O1	−3.1 (5)	C22—C17—C18—C19	3.2 (5)
C1—C2—C10—C11	−78.7 (5)	C16—C17—C18—C19	179.0 (3)
C3—C2—C10—C11	106.0 (5)	C17—C18—C19—C20	−1.8 (5)
C10'—C2—C10—C11	6.5 (13)	C18—C19—C20—C21	−0.7 (6)
C1—C2—C10—C14	103.2 (4)	C19—C20—C21—C22	1.7 (6)
C3—C2—C10—C14	−72.0 (5)	C20—C21—C22—C17	−0.2 (5)
C10'—C2—C10—C14	−171.6 (13)	C18—C17—C22—C21	−2.2 (5)
C2—C10—C11—C12	−1.3 (6)	C16—C17—C22—C21	−177.8 (3)
C14—C10—C11—C12	176.8 (4)	C24—O10—C23—O9	0.9 (5)
C1—C2—C10'—C11'	125.0 (18)	C24—O10—C23—C7	−178.3 (3)
C3—C2—C10'—C11'	−91 (2)	C8—C7—C23—O9	153.5 (4)
C10—C2—C10'—C11'	10.6 (14)	C6—C7—C23—O9	−26.5 (5)
C1—C2—C10'—C12	−51 (2)	C8—C7—C23—O10	−27.4 (4)
C3—C2—C10'—C12	93 (2)	C6—C7—C23—O10	152.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O8	0.99 (6)	1.65 (6)	2.541 (4)	149 (5)
C13—H13C···O3i	0.96	2.64	3.467 (5)	145
C15—H15C···O2ii	0.96	2.53	3.342 (5)	142
C22—H22A···O8iii	0.93	2.49	3.316 (5)	149
C24—H24A···O5iv	0.96	2.67	3.392 (5)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O8	0.99 (6)	1.65 (6)	2.541 (4)	149 (5)
C13—H13C⋯O3i	0.96	2.64	3.467 (5)	145
C15—H15C⋯O2ii	0.96	2.53	3.342 (5)	142
C22—H22A⋯O8iii	0.93	2.49	3.316 (5)	149
C24—H24A⋯O5iv	0.96	2.67	3.392 (5)	133

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .