1,8-Bis(4-chloro-benzo-yl)-7-meth-oxy-naphthalen-2-ol ethanol monosolvate.

In the title compound, C(25)H(16)Cl(2)O(4)·C(2)H(6)O, the two 4-chloro-benzoyl groups are in syn orientations with respect to the naphthalene ring system and are approximately parallel to each other: the dihedral angle between the benzene rings is 11.43 (16)°. The conformation around each of the carbonyl C-(C=O)-C groups forms a larger angle to the plane of the naphthalene ring system than that to the benzene ring; the angles of the C=O bond vector with the naphthalene ring system and the benzene ring are 55.4 (3) versus 13.5 (3)° and 52.2 (3) versus 17.9 (3)°. An intra-molecular O-H⋯O=C hydrogen bond generates a six-membered ring. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds including the ethanol solvent mol-ecule are observed. A C-H⋯O inter-action also occurs. The ethyl group of the ethanol mol-ecule is disordered over two positions with site occupancies of 0.63 and 0.37. The crystal studied was an inversion twin.

Related literature

For the structures of closely related compounds, see: Mitsui et al. (2008 ▶); Nakaema et al. (2007 ▶).

Experimental

Crystal data

C25H16Cl2O4·C2H6O

M = 497.35

Tetragonal,

a = 25.2992 (5) Å

c = 7.3068 (2) Å

V = 4676.71 (18) Å3

Z = 8

Cu Kα radiation

μ = 2.81 mm−1

T = 193 K

0.60 × 0.10 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.283, T max = 0.766

43771 measured reflections

4272 independent reflections

3676 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.146

S = 1.11

4272 reflections

322 parameters

50 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1951 Friedel pairs

Flack parameter: 0.425 (17)

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024074/is2562sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024074/is2562Isup2.hkl

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

C25H16Cl2O4·C2H6O	Dx = 1.413 Mg m−3
Mr = 497.35	Melting point = 505.5–506.5 K
Tetragonal, I4	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: I -4	Cell parameters from 34431 reflections
a = 25.2992 (5) Å	θ = 3.5–68.2°
c = 7.3068 (2) Å	µ = 2.81 mm−1
V = 4676.71 (18) Å3	T = 193 K
Z = 8	Platelet, yellow
F(000) = 2064	0.60 × 0.10 × 0.10 mm

Rigaku R-AXIS RAPID diffractometer	4272 independent reflections
Radiation source: rotating anode	3676 reflections with I > 2σ(I)
graphite	Rint = 0.059
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 3.5°
ω scans	h = −30→30
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −29→30
Tmin = 0.283, Tmax = 0.766	l = −8→8
43771 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.050	w = 1/[σ2(Fo2) + (0.0883P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.146	(Δ/σ)max = 0.001
S = 1.11	Δρmax = 0.41 e Å−3
4272 reflections	Δρmin = −0.24 e Å−3
322 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
50 restraints	Extinction coefficient: 0.00147 (14)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1951 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.425 (17)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.05719 (3)	0.03898 (3)	0.17865 (14)	0.0621 (3)
Cl2	−0.02496 (4)	0.16783 (4)	0.08841 (16)	0.0770 (3)
O1	0.11592 (9)	0.21618 (9)	0.8263 (4)	0.0551 (6)
O2	0.04808 (10)	0.31611 (10)	0.8034 (4)	0.0612 (6)
O3	0.23047 (8)	0.17133 (9)	0.6041 (4)	0.0598 (6)
O4	0.07574 (10)	0.41241 (9)	0.6105 (4)	0.0678 (7)
H4O	0.0566	0.3955	0.6795	0.081*
C1	0.17824 (11)	0.24765 (13)	0.6109 (5)	0.0479 (7)
C2	0.22785 (13)	0.22437 (13)	0.5843 (5)	0.0522 (8)
C3	0.27296 (13)	0.25544 (15)	0.5449 (5)	0.0566 (9)
H3	0.3063	0.2393	0.5240	0.068*
C4	0.26750 (14)	0.30881 (15)	0.5375 (5)	0.0584 (9)
H4	0.2979	0.3298	0.5153	0.070*
C5	0.21886 (14)	0.33392 (14)	0.5614 (5)	0.0545 (8)
C6	0.21545 (15)	0.39011 (14)	0.5502 (5)	0.0612 (9)
H6	0.2467	0.4099	0.5287	0.073*
C7	0.16923 (16)	0.41585 (14)	0.5690 (6)	0.0645 (10)
H7	0.1681	0.4533	0.5609	0.077*
C8	0.12273 (14)	0.38691 (13)	0.6008 (5)	0.0560 (8)
C9	0.12359 (12)	0.33224 (12)	0.6194 (5)	0.0506 (8)
C10	0.17206 (12)	0.30356 (13)	0.5983 (5)	0.0489 (7)
C11	0.13535 (12)	0.21062 (13)	0.6754 (5)	0.0488 (7)
C12	0.11815 (12)	0.16695 (12)	0.5514 (5)	0.0464 (7)
C13	0.13067 (13)	0.16708 (13)	0.3672 (5)	0.0521 (8)
H13	0.1527	0.1942	0.3194	0.063*
C14	0.11142 (14)	0.12794 (14)	0.2511 (5)	0.0548 (8)
H14	0.1190	0.1288	0.1238	0.066*
C15	0.08117 (12)	0.08796 (12)	0.3244 (5)	0.0501 (7)
C16	0.06922 (13)	0.08626 (13)	0.5068 (5)	0.0535 (8)
H16	0.0488	0.0579	0.5545	0.064*
C17	0.08686 (12)	0.12576 (13)	0.6207 (5)	0.0527 (8)
H17	0.0778	0.1252	0.7469	0.063*
C18	0.07059 (13)	0.30794 (12)	0.6591 (5)	0.0513 (8)
C19	0.04529 (13)	0.27497 (13)	0.5116 (5)	0.0510 (8)
C20	0.06054 (14)	0.27961 (14)	0.3330 (6)	0.0572 (8)
H20	0.0868	0.3047	0.3000	0.069*
C21	0.03752 (15)	0.24741 (15)	0.1975 (6)	0.0625 (9)
H21	0.0478	0.2503	0.0729	0.075*
C22	−0.00009 (14)	0.21190 (14)	0.2508 (6)	0.0588 (9)
C23	−0.01677 (14)	0.20716 (14)	0.4298 (6)	0.0610 (9)
H23	−0.0430	0.1820	0.4622	0.073*
C24	0.00536 (13)	0.23966 (13)	0.5612 (6)	0.0560 (8)
H24	−0.0065	0.2380	0.6844	0.067*
C25	0.28018 (15)	0.14558 (17)	0.5787 (7)	0.0720 (11)
H25A	0.2756	0.1073	0.5930	0.086*
H25B	0.3054	0.1585	0.6700	0.086*
H25C	0.2936	0.1532	0.4556	0.086*
C26	0.10138 (18)	0.4338 (3)	0.0813 (9)	0.1041 (17)
H26A	0.1190	0.4317	0.2004	0.125*	0.63
H26B	0.1041	0.4700	0.0339	0.125*	0.63
H26C	0.1183	0.4093	−0.0045	0.125*	0.63
H26D	0.1226	0.4626	0.1330	0.125*	0.37
H26E	0.1193	0.4193	−0.0264	0.125*	0.37
H26F	0.0969	0.4059	0.1731	0.125*	0.37
C27A	0.0461 (3)	0.4197 (4)	0.1019 (11)	0.092 (2)	0.63
H27A	0.0445	0.3839	0.1557	0.111*	0.63
H27B	0.0302	0.4443	0.1919	0.111*	0.63
C27B	0.0485 (4)	0.4546 (5)	0.028 (2)	0.092 (4)	0.37
H27C	0.0313	0.4689	0.1394	0.110*	0.37
H27D	0.0539	0.4845	−0.0571	0.110*	0.37
O5	0.01506 (14)	0.42004 (17)	−0.0507 (6)	0.1179 (14)
H5O	−0.0194 (3)	0.4263 (11)	−0.026 (3)	0.141*

	U11	U22	U33	U12	U13	U23
Cl1	0.0672 (5)	0.0567 (5)	0.0624 (6)	−0.0070 (4)	−0.0069 (4)	−0.0074 (4)
Cl2	0.0848 (6)	0.0637 (5)	0.0826 (7)	0.0000 (4)	−0.0310 (6)	−0.0117 (5)
O1	0.0530 (12)	0.0687 (14)	0.0436 (13)	−0.0058 (10)	0.0053 (11)	−0.0048 (11)
O2	0.0612 (14)	0.0643 (14)	0.0580 (16)	−0.0030 (11)	0.0122 (13)	−0.0105 (13)
O3	0.0514 (12)	0.0651 (14)	0.0630 (16)	0.0046 (10)	0.0009 (12)	−0.0015 (12)
O4	0.0671 (15)	0.0577 (14)	0.0787 (19)	−0.0015 (11)	0.0040 (14)	0.0011 (13)
C1	0.0464 (15)	0.0612 (18)	0.0363 (17)	−0.0059 (13)	0.0009 (13)	−0.0056 (14)
C2	0.0526 (18)	0.063 (2)	0.0414 (18)	−0.0029 (14)	−0.0019 (15)	−0.0039 (16)
C3	0.0462 (17)	0.078 (2)	0.0453 (19)	−0.0041 (15)	0.0027 (15)	−0.0040 (17)
C4	0.055 (2)	0.077 (2)	0.0428 (19)	−0.0147 (17)	−0.0010 (16)	−0.0027 (17)
C5	0.0551 (18)	0.066 (2)	0.0423 (18)	−0.0132 (15)	0.0018 (15)	−0.0058 (16)
C6	0.069 (2)	0.063 (2)	0.052 (2)	−0.0227 (17)	0.0005 (18)	−0.0029 (17)
C7	0.074 (2)	0.0544 (19)	0.065 (2)	−0.0153 (17)	0.002 (2)	−0.0025 (18)
C8	0.0626 (19)	0.0550 (18)	0.051 (2)	−0.0080 (15)	0.0049 (17)	−0.0070 (16)
C9	0.0531 (17)	0.0539 (17)	0.0447 (18)	−0.0067 (13)	0.0020 (15)	−0.0040 (15)
C10	0.0501 (17)	0.0591 (18)	0.0374 (17)	−0.0100 (13)	−0.0018 (14)	−0.0068 (14)
C11	0.0437 (15)	0.0582 (18)	0.0446 (18)	−0.0023 (13)	0.0004 (15)	−0.0016 (16)
C12	0.0424 (15)	0.0536 (17)	0.0431 (18)	0.0012 (12)	−0.0031 (14)	−0.0002 (14)
C13	0.0530 (17)	0.0567 (18)	0.047 (2)	−0.0071 (13)	0.0036 (15)	0.0008 (15)
C14	0.0595 (19)	0.062 (2)	0.0432 (18)	−0.0040 (16)	0.0029 (15)	−0.0015 (16)
C15	0.0479 (16)	0.0499 (16)	0.0527 (19)	−0.0020 (13)	−0.0034 (15)	−0.0039 (16)
C16	0.0545 (18)	0.0499 (18)	0.056 (2)	−0.0046 (14)	0.0048 (15)	0.0036 (15)
C17	0.0553 (17)	0.0524 (17)	0.050 (2)	0.0004 (14)	0.0052 (15)	0.0027 (15)
C18	0.0519 (17)	0.0506 (17)	0.051 (2)	−0.0009 (13)	0.0021 (16)	−0.0004 (15)
C19	0.0485 (17)	0.0518 (18)	0.053 (2)	0.0015 (14)	−0.0018 (15)	−0.0007 (15)
C20	0.0587 (19)	0.0565 (19)	0.056 (2)	−0.0049 (15)	−0.0040 (17)	0.0011 (17)
C21	0.071 (2)	0.066 (2)	0.050 (2)	0.0013 (17)	−0.0074 (18)	−0.0045 (18)
C22	0.058 (2)	0.0518 (19)	0.066 (2)	0.0023 (15)	−0.0163 (17)	−0.0054 (17)
C23	0.0553 (19)	0.0515 (18)	0.076 (3)	−0.0047 (14)	−0.0056 (19)	−0.0023 (18)
C24	0.0534 (18)	0.0540 (18)	0.061 (2)	−0.0039 (14)	0.0014 (16)	0.0005 (17)
C25	0.068 (2)	0.080 (3)	0.067 (3)	0.0053 (18)	0.006 (2)	−0.002 (2)
C26	0.078 (3)	0.140 (5)	0.095 (4)	0.015 (3)	−0.018 (3)	−0.023 (4)
C27A	0.104 (5)	0.093 (5)	0.080 (6)	0.009 (4)	−0.002 (4)	−0.002 (4)
C27B	0.080 (7)	0.095 (9)	0.102 (11)	−0.004 (6)	0.001 (7)	−0.012 (8)
O5	0.0704 (19)	0.158 (3)	0.125 (4)	0.016 (2)	−0.007 (2)	−0.054 (3)

Cl1—C15	1.743 (3)	C16—C17	1.375 (5)
Cl2—C22	1.746 (4)	C16—H16	0.9500
O1—C11	1.215 (4)	C17—H17	0.9500
O2—C18	1.216 (4)	C18—C19	1.506 (5)
O3—C2	1.351 (4)	C19—C20	1.366 (6)
O3—C25	1.428 (4)	C19—C24	1.396 (5)
O4—C8	1.354 (4)	C20—C21	1.408 (5)
O4—H4O	0.8200	C20—H20	0.9500
C1—C2	1.400 (5)	C21—C22	1.365 (5)
C1—C10	1.426 (5)	C21—H21	0.9500
C1—C11	1.509 (4)	C22—C23	1.379 (6)
C2—C3	1.415 (5)	C23—C24	1.383 (5)
C3—C4	1.358 (5)	C23—H23	0.9500
C3—H3	0.9500	C24—H24	0.9500
C4—C5	1.396 (5)	C25—H25A	0.9800
C4—H4	0.9500	C25—H25B	0.9800
C5—C6	1.427 (5)	C25—H25C	0.9800
C5—C10	1.437 (4)	C26—C27A	1.451 (7)
C6—C7	1.345 (6)	C26—C27B	1.488 (8)
C6—H6	0.9500	C26—H26A	0.9800
C7—C8	1.405 (5)	C26—H26B	0.9800
C7—H7	0.9500	C26—H26C	0.9800
C8—C9	1.390 (5)	C26—H26D	0.9800
C9—C10	1.433 (5)	C26—H26E	0.9800
C9—C18	1.503 (4)	C26—H26F	0.9800
C11—C12	1.494 (5)	C27A—O5	1.364 (7)
C12—C13	1.382 (5)	C27A—H27A	0.9900
C12—C17	1.403 (4)	C27A—H27B	0.9900
C13—C14	1.392 (5)	C27B—O5	1.347 (8)
C13—H13	0.9500	C27B—H27C	0.9900
C14—C15	1.377 (5)	C27B—H27D	0.9900
C14—H14	0.9500	O5—H5O	0.904 (10)
C15—C16	1.367 (5)
C2—O3—C25	118.8 (3)	O2—C18—C9	121.0 (3)
C8—O4—H4O	107.7	O2—C18—C19	121.1 (3)
C2—C1—C10	120.4 (3)	C9—C18—C19	117.9 (3)
C2—C1—C11	115.3 (3)	C20—C19—C24	120.5 (3)
C10—C1—C11	123.9 (3)	C20—C19—C18	121.1 (3)
O3—C2—C1	116.5 (3)	C24—C19—C18	118.4 (3)
O3—C2—C3	122.3 (3)	C19—C20—C21	120.3 (3)
C1—C2—C3	121.2 (3)	C19—C20—H20	119.8
C4—C3—C2	118.6 (3)	C21—C20—H20	119.8
C4—C3—H3	120.7	C22—C21—C20	117.9 (4)
C2—C3—H3	120.7	C22—C21—H21	121.0
C3—C4—C5	122.5 (3)	C20—C21—H21	121.0
C3—C4—H4	118.8	C21—C22—C23	122.7 (3)
C5—C4—H4	118.8	C21—C22—Cl2	118.5 (3)
C4—C5—C6	120.0 (3)	C23—C22—Cl2	118.6 (3)
C4—C5—C10	120.4 (3)	C22—C23—C24	118.9 (3)
C6—C5—C10	119.6 (3)	C22—C23—H23	120.6
C7—C6—C5	121.9 (3)	C24—C23—H23	120.6
C7—C6—H6	119.0	C23—C24—C19	119.5 (4)
C5—C6—H6	119.0	C23—C24—H24	120.2
C6—C7—C8	119.5 (3)	C19—C24—H24	120.2
C6—C7—H7	120.2	O3—C25—H25A	109.5
C8—C7—H7	120.2	O3—C25—H25B	109.5
O4—C8—C9	118.9 (3)	H25A—C25—H25B	109.5
O4—C8—C7	119.7 (3)	O3—C25—H25C	109.5
C9—C8—C7	121.4 (3)	H25A—C25—H25C	109.5
C8—C9—C10	120.4 (3)	H25B—C25—H25C	109.5
C8—C9—C18	114.3 (3)	C27A—C26—H26A	109.5
C10—C9—C18	125.2 (3)	C27A—C26—H26B	109.5
C1—C10—C9	126.1 (3)	H26A—C26—H26B	109.5
C1—C10—C5	116.9 (3)	C27A—C26—H26C	109.5
C9—C10—C5	117.0 (3)	H26A—C26—H26C	109.5
O1—C11—C12	121.2 (3)	H26B—C26—H26C	109.5
O1—C11—C1	120.2 (3)	C27B—C26—H26D	109.3
C12—C11—C1	118.6 (3)	C27B—C26—H26E	109.9
C13—C12—C17	118.8 (3)	H26D—C26—H26E	109.5
C13—C12—C11	121.5 (3)	C27B—C26—H26F	109.2
C17—C12—C11	119.6 (3)	H26D—C26—H26F	109.5
C12—C13—C14	120.8 (3)	H26E—C26—H26F	109.5
C12—C13—H13	119.6	O5—C27A—C26	117.9 (6)
C14—C13—H13	119.6	O5—C27A—H27A	107.8
C15—C14—C13	118.7 (3)	C26—C27A—H27A	107.8
C15—C14—H14	120.7	O5—C27A—H27B	107.8
C13—C14—H14	120.7	C26—C27A—H27B	107.8
C16—C15—C14	121.7 (3)	H27A—C27A—H27B	107.2
C16—C15—Cl1	119.8 (3)	O5—C27B—C26	116.6 (8)
C14—C15—Cl1	118.5 (3)	O5—C27B—H27C	108.1
C15—C16—C17	119.7 (3)	C26—C27B—H27C	108.1
C15—C16—H16	120.2	O5—C27B—H27D	108.1
C17—C16—H16	120.2	C26—C27B—H27D	108.1
C16—C17—C12	120.3 (3)	H27C—C27B—H27D	107.3
C16—C17—H17	119.9	C27B—O5—H5O	114.2 (14)
C12—C17—H17	119.9	C27A—O5—H5O	113.4 (14)
C25—O3—C2—C1	−179.9 (3)	O1—C11—C12—C13	165.1 (3)
C25—O3—C2—C3	−2.0 (5)	C1—C11—C12—C13	−15.8 (5)
C10—C1—C2—O3	178.1 (3)	O1—C11—C12—C17	−12.4 (5)
C11—C1—C2—O3	5.4 (5)	C1—C11—C12—C17	166.7 (3)
C10—C1—C2—C3	0.1 (5)	C17—C12—C13—C14	1.8 (5)
C11—C1—C2—C3	−172.5 (3)	C11—C12—C13—C14	−175.7 (3)
O3—C2—C3—C4	−176.3 (3)	C12—C13—C14—C15	−2.3 (5)
C1—C2—C3—C4	1.6 (5)	C13—C14—C15—C16	0.8 (5)
C2—C3—C4—C5	−2.2 (5)	C13—C14—C15—Cl1	−179.9 (3)
C3—C4—C5—C6	−179.3 (4)	C14—C15—C16—C17	1.1 (5)
C3—C4—C5—C10	1.1 (5)	Cl1—C15—C16—C17	−178.1 (2)
C4—C5—C6—C7	178.8 (4)	C15—C16—C17—C12	−1.6 (5)
C10—C5—C6—C7	−1.6 (6)	C13—C12—C17—C16	0.2 (5)
C5—C6—C7—C8	0.0 (6)	C11—C12—C17—C16	177.8 (3)
C6—C7—C8—O4	−176.6 (4)	C8—C9—C18—O2	−67.1 (4)
C6—C7—C8—C9	2.2 (6)	C10—C9—C18—O2	113.8 (4)
O4—C8—C9—C10	176.0 (3)	C8—C9—C18—C19	110.5 (4)
C7—C8—C9—C10	−2.8 (6)	C10—C9—C18—C19	−68.6 (5)
O4—C8—C9—C18	−3.2 (5)	O2—C18—C19—C20	157.9 (4)
C7—C8—C9—C18	178.1 (4)	C9—C18—C19—C20	−19.7 (5)
C2—C1—C10—C9	178.9 (3)	O2—C18—C19—C24	−21.6 (5)
C11—C1—C10—C9	−9.1 (5)	C9—C18—C19—C24	160.9 (3)
C2—C1—C10—C5	−1.2 (5)	C24—C19—C20—C21	−2.3 (5)
C11—C1—C10—C5	170.8 (3)	C18—C19—C20—C21	178.2 (3)
C8—C9—C10—C1	−178.9 (3)	C19—C20—C21—C22	0.0 (5)
C18—C9—C10—C1	0.2 (6)	C20—C21—C22—C23	1.2 (6)
C8—C9—C10—C5	1.2 (5)	C20—C21—C22—Cl2	−174.6 (3)
C18—C9—C10—C5	−179.8 (3)	C21—C22—C23—C24	0.0 (6)
C4—C5—C10—C1	0.6 (5)	Cl2—C22—C23—C24	175.8 (3)
C6—C5—C10—C1	−179.0 (3)	C22—C23—C24—C19	−2.4 (5)
C4—C5—C10—C9	−179.4 (3)	C20—C19—C24—C23	3.5 (5)
C6—C5—C10—C9	0.9 (5)	C18—C19—C24—C23	−177.0 (3)
C2—C1—C11—O1	114.4 (4)	C27B—C26—C27A—O5	49.3 (9)
C10—C1—C11—O1	−58.0 (5)	C27A—C26—C27B—O5	−49.3 (9)
C2—C1—C11—C12	−64.7 (4)	C26—C27B—O5—C27A	48.9 (9)
C10—C1—C11—C12	122.9 (3)	C26—C27A—O5—C27B	−51.4 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O2	0.82	2.21	2.900 (4)	141
O4—H4O···O5i	0.82	2.32	2.919 (5)	131
O5—H5O···O4ii	0.90 (1)	1.83 (1)	2.636 (4)	147 (2)
C21—H21···O2iii	0.95	2.58	3.374 (5)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O2	0.82	2.21	2.900 (4)	141
O4—H4O⋯O5i	0.82	2.32	2.919 (5)	131
O5—H5O⋯O4ii	0.90 (1)	1.83 (1)	2.636 (4)	147 (2)
C21—H21⋯O2iii	0.95	2.58	3.374 (5)	141

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