4-(5-Hy-droxy-meth-yl-2-meth-oxy-phen-oxy)benzoic acid.

The title compound, C(15)H(14)O(5), crystallizes with two independent mol-ecules in the asymmetric unit in which the benzene rings are inclined at dihedral angles of 79.4 (1) and 84.2 (1)°. In the crystal, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into double chains propagating in [001].

Related literature

For the bioactivity of diphenyl ether derivatives, see: Asakawa (2001 ▶); Hua et al. (2009 ▶); Kini et al.(2009 ▶). For background to Ullman coupling, see: Bringmann et al. (1990 ▶).

Experimental

Crystal data

C15H14O5

M = 274.26

Triclinic,

a = 10.5420 (15) Å

b = 10.6153 (15) Å

c = 12.8070 (18) Å

α = 78.024 (2)°

β = 75.184 (2)°

γ = 88.451 (2)°

V = 1354.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 273 K

0.13 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.987, T max = 0.990

5794 measured reflections

3874 independent reflections

3154 reflections with I > 2σ(I)

R int = 0.015

θmax = 23.3°

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.141

S = 1.02

3874 reflections

365 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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/S1600536811012190/cv5067sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012190/cv5067Isup2.hkl

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

C15H14O5	Z = 4
Mr = 274.26	F(000) = 576
Triclinic, P1	Dx = 1.345 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.5420 (15) Å	Cell parameters from 2550 reflections
b = 10.6153 (15) Å	θ = 2.8–23.3°
c = 12.8070 (18) Å	µ = 0.10 mm−1
α = 78.024 (2)°	T = 273 K
β = 75.184 (2)°	Block, colourless
γ = 88.451 (2)°	0.13 × 0.12 × 0.10 mm
V = 1354.9 (3) Å3

Bruker APEXII CCD diffractometer	3874 independent reflections
Radiation source: fine-focus sealed tube	3154 reflections with I > 2σ(I)
graphite	Rint = 0.015
phi and ω scans	θmax = 23.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
Tmin = 0.987, Tmax = 0.990	k = −11→5
5794 measured reflections	l = −14→13

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.093P)2 + 0.1798P] where P = (Fo2 + 2Fc2)/3
3874 reflections	(Δ/σ)max < 0.001
365 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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
O8	0.45863 (12)	0.12659 (13)	0.65556 (10)	0.0507 (4)
O7	0.68968 (14)	0.00872 (15)	0.63970 (12)	0.0595 (4)
C22	0.52664 (18)	0.12698 (18)	0.73608 (16)	0.0447 (5)
C16	0.51038 (17)	0.20109 (18)	0.55175 (15)	0.0424 (5)
C19	0.60706 (19)	0.33828 (19)	0.33809 (16)	0.0480 (5)
C20	0.5219 (2)	0.2327 (2)	0.35983 (17)	0.0500 (5)
H20A	0.4978	0.2079	0.3019	0.060*
C23	0.64416 (19)	0.06201 (18)	0.73023 (16)	0.0470 (5)
C21	0.47319 (19)	0.16482 (19)	0.46587 (16)	0.0475 (5)
H21A	0.4156	0.0949	0.4799	0.057*
C27	0.4736 (2)	0.1865 (2)	0.82238 (16)	0.0510 (5)
H27A	0.3956	0.2301	0.8245	0.061*
C24	0.7062 (2)	0.0578 (2)	0.81386 (18)	0.0566 (6)
H24A	0.7845	0.0148	0.8119	0.068*
C17	0.5919 (2)	0.30742 (19)	0.53229 (17)	0.0511 (5)
H17A	0.6142	0.3332	0.5905	0.061*
O10	0.6491 (2)	0.36489 (19)	0.14387 (14)	0.0957 (7)
O9	0.7344 (2)	0.50767 (18)	0.21132 (13)	0.0866 (6)
H9	0.7690	0.5355	0.1457	0.130*
C18	0.6399 (2)	0.3752 (2)	0.42520 (16)	0.0520 (5)
H18A	0.6952	0.4469	0.4116	0.062*
C26	0.5356 (2)	0.1820 (2)	0.90646 (16)	0.0543 (5)
C25	0.6514 (2)	0.1177 (2)	0.90050 (18)	0.0605 (6)
H25A	0.6940	0.1144	0.9562	0.073*
C28	0.6631 (2)	0.4042 (2)	0.22227 (18)	0.0590 (6)
C29	0.8069 (3)	−0.0626 (3)	0.6332 (2)	0.0796 (8)
H29A	0.8279	−0.0952	0.5665	0.119*
H29B	0.7942	−0.1332	0.6957	0.119*
H29C	0.8776	−0.0074	0.6331	0.119*
O3	1.04180 (13)	0.76114 (15)	0.31213 (12)	0.0619 (4)
C7	0.9680 (2)	0.70611 (19)	0.41650 (17)	0.0502 (5)
O2	0.89962 (16)	0.97320 (16)	0.31548 (14)	0.0700 (5)
O5	0.8207 (2)	0.5321 (2)	0.82261 (14)	0.0896 (6)
C1	0.97799 (19)	0.8027 (2)	0.22881 (17)	0.0516 (5)
C12	0.8381 (2)	0.66884 (19)	0.43978 (17)	0.0501 (5)
H12A	0.7941	0.6824	0.3842	0.060*
C10	0.8387 (2)	0.59194 (19)	0.63005 (17)	0.0524 (5)
C11	0.7735 (2)	0.61085 (19)	0.54690 (17)	0.0503 (5)
H11A	0.6860	0.5844	0.5632	0.060*
C3	0.9363 (2)	0.7804 (2)	0.05822 (17)	0.0560 (6)
C6	0.90656 (19)	0.9154 (2)	0.22828 (17)	0.0517 (5)
C2	0.9932 (2)	0.7374 (2)	0.14517 (18)	0.0561 (5)
H2A	1.0423	0.6632	0.1466	0.067*
O4	0.65453 (19)	0.48294 (19)	0.75911 (13)	0.0810 (5)
H4	0.6192	0.4596	0.8251	0.122*
C8	1.0346 (2)	0.6871 (2)	0.4979 (2)	0.0612 (6)
H8A	1.1225	0.7124	0.4811	0.073*
C15	0.7709 (3)	0.5337 (2)	0.74642 (18)	0.0630 (6)
C5	0.8493 (2)	0.9587 (2)	0.14235 (19)	0.0589 (6)
H5A	0.8006	1.0331	0.1406	0.071*
C9	0.9694 (2)	0.6303 (2)	0.60459 (19)	0.0616 (6)
H9A	1.0137	0.6177	0.6599	0.074*
C4	0.8646 (2)	0.8908 (2)	0.05883 (18)	0.0603 (6)
H4A	0.8254	0.9206	0.0014	0.072*
C14	0.9473 (3)	0.7054 (3)	−0.03082 (19)	0.0724 (7)
H14A	0.9394	0.7625	−0.0984	0.087*
H14B	1.0321	0.6655	−0.0453	0.087*
C13	0.8180 (3)	1.0823 (2)	0.3227 (2)	0.0787 (7)
H13A	0.8209	1.1140	0.3870	0.118*
H13B	0.7294	1.0575	0.3279	0.118*
H13C	0.8490	1.1487	0.2580	0.118*
O6	0.5358 (2)	0.37953 (16)	0.96729 (14)	0.0863 (6)
H6	0.5827	0.3883	1.0075	0.129*
O1	0.8463 (2)	0.6102 (2)	0.00454 (13)	0.0946 (7)
H1	0.8407	0.5796	−0.0479	0.142*
C30	0.4822 (3)	0.2530 (3)	0.99757 (19)	0.0717 (7)
H30A	0.3874	0.2556	1.0121	0.086*
H30B	0.5041	0.2083	1.0646	0.086*

	U11	U22	U33	U12	U13	U23
O8	0.0490 (8)	0.0603 (9)	0.0454 (8)	−0.0110 (6)	−0.0185 (6)	−0.0068 (7)
O7	0.0618 (9)	0.0643 (9)	0.0656 (10)	0.0097 (7)	−0.0272 (7)	−0.0302 (8)
C22	0.0472 (11)	0.0465 (11)	0.0426 (11)	−0.0110 (9)	−0.0170 (9)	−0.0060 (9)
C16	0.0414 (10)	0.0445 (11)	0.0446 (11)	0.0036 (8)	−0.0165 (8)	−0.0102 (9)
C19	0.0531 (11)	0.0491 (11)	0.0458 (11)	0.0032 (9)	−0.0194 (9)	−0.0108 (9)
C20	0.0585 (12)	0.0534 (12)	0.0479 (12)	−0.0010 (10)	−0.0275 (10)	−0.0148 (10)
C23	0.0549 (12)	0.0412 (11)	0.0484 (12)	−0.0052 (9)	−0.0197 (9)	−0.0082 (9)
C21	0.0477 (11)	0.0470 (11)	0.0546 (13)	−0.0028 (9)	−0.0240 (9)	−0.0119 (10)
C27	0.0496 (11)	0.0546 (12)	0.0478 (12)	−0.0043 (9)	−0.0104 (9)	−0.0102 (10)
C24	0.0651 (13)	0.0525 (12)	0.0597 (13)	0.0017 (10)	−0.0315 (11)	−0.0090 (10)
C17	0.0613 (12)	0.0504 (12)	0.0479 (12)	−0.0092 (10)	−0.0214 (10)	−0.0136 (9)
O10	0.1400 (18)	0.1021 (15)	0.0491 (10)	−0.0394 (13)	−0.0320 (10)	−0.0091 (10)
O9	0.1231 (15)	0.0779 (12)	0.0519 (10)	−0.0380 (11)	−0.0120 (10)	−0.0062 (9)
C18	0.0616 (13)	0.0464 (11)	0.0518 (13)	−0.0090 (10)	−0.0193 (10)	−0.0111 (10)
C26	0.0656 (14)	0.0556 (13)	0.0401 (11)	−0.0127 (11)	−0.0113 (10)	−0.0075 (9)
C25	0.0786 (16)	0.0599 (14)	0.0505 (13)	−0.0066 (12)	−0.0334 (11)	−0.0063 (10)
C28	0.0713 (14)	0.0584 (14)	0.0496 (13)	−0.0051 (11)	−0.0208 (11)	−0.0089 (11)
C29	0.0760 (16)	0.0827 (18)	0.099 (2)	0.0262 (14)	−0.0367 (15)	−0.0474 (16)
O3	0.0482 (8)	0.0761 (10)	0.0612 (10)	0.0049 (7)	−0.0208 (7)	−0.0056 (8)
C7	0.0533 (12)	0.0481 (12)	0.0552 (13)	0.0113 (9)	−0.0229 (10)	−0.0143 (10)
O2	0.0745 (10)	0.0656 (10)	0.0815 (11)	0.0104 (8)	−0.0311 (9)	−0.0285 (9)
O5	0.1208 (15)	0.1074 (15)	0.0559 (10)	0.0156 (12)	−0.0428 (11)	−0.0273 (10)
C1	0.0435 (11)	0.0556 (13)	0.0555 (13)	−0.0004 (9)	−0.0175 (9)	−0.0046 (10)
C12	0.0549 (12)	0.0488 (11)	0.0534 (12)	0.0040 (9)	−0.0265 (10)	−0.0103 (10)
C10	0.0704 (14)	0.0436 (11)	0.0539 (13)	0.0145 (10)	−0.0288 (11)	−0.0196 (9)
C11	0.0600 (12)	0.0445 (11)	0.0537 (13)	0.0056 (9)	−0.0246 (10)	−0.0141 (10)
C3	0.0550 (12)	0.0602 (14)	0.0467 (12)	−0.0099 (10)	−0.0066 (10)	−0.0038 (10)
C6	0.0452 (11)	0.0513 (12)	0.0570 (13)	−0.0050 (9)	−0.0114 (9)	−0.0085 (10)
C2	0.0527 (12)	0.0523 (12)	0.0594 (14)	0.0043 (10)	−0.0105 (10)	−0.0084 (11)
O4	0.1012 (14)	0.0868 (13)	0.0534 (10)	−0.0133 (11)	−0.0265 (9)	−0.0004 (9)
C8	0.0554 (13)	0.0679 (14)	0.0722 (16)	0.0094 (11)	−0.0329 (12)	−0.0211 (12)
C15	0.0921 (18)	0.0545 (13)	0.0526 (14)	0.0174 (13)	−0.0313 (13)	−0.0201 (11)
C5	0.0561 (13)	0.0518 (13)	0.0648 (14)	0.0032 (10)	−0.0176 (11)	−0.0007 (11)
C9	0.0741 (15)	0.0658 (14)	0.0603 (15)	0.0166 (12)	−0.0390 (12)	−0.0221 (12)
C4	0.0563 (13)	0.0685 (15)	0.0512 (13)	−0.0053 (11)	−0.0170 (10)	0.0033 (11)
C14	0.0780 (16)	0.0839 (18)	0.0500 (13)	−0.0120 (14)	−0.0063 (11)	−0.0131 (12)
C13	0.0876 (18)	0.0606 (15)	0.0837 (18)	0.0078 (13)	−0.0080 (14)	−0.0234 (13)
O6	0.1443 (18)	0.0613 (11)	0.0554 (10)	−0.0033 (11)	−0.0256 (10)	−0.0161 (8)
O1	0.1292 (16)	0.1022 (15)	0.0485 (10)	−0.0476 (13)	−0.0084 (10)	−0.0180 (10)
C30	0.0852 (17)	0.0803 (17)	0.0516 (14)	−0.0086 (13)	−0.0136 (12)	−0.0216 (12)

O8—C16	1.381 (2)	O2—C6	1.367 (3)
O8—C22	1.399 (2)	O2—C13	1.428 (3)
O7—C23	1.367 (2)	O5—C15	1.218 (3)
O7—C29	1.425 (3)	C1—C2	1.367 (3)
C22—C27	1.374 (3)	C1—C6	1.396 (3)
C22—C23	1.394 (3)	C12—C11	1.385 (3)
C16—C17	1.378 (3)	C12—H12A	0.9300
C16—C21	1.384 (3)	C10—C9	1.384 (3)
C19—C18	1.380 (3)	C10—C11	1.388 (3)
C19—C20	1.392 (3)	C10—C15	1.487 (3)
C19—C28	1.477 (3)	C11—H11A	0.9300
C20—C21	1.373 (3)	C3—C4	1.377 (3)
C20—H20A	0.9300	C3—C2	1.387 (3)
C23—C24	1.383 (3)	C3—C14	1.500 (3)
C21—H21A	0.9300	C6—C5	1.379 (3)
C27—C26	1.387 (3)	C2—H2A	0.9300
C27—H27A	0.9300	O4—C15	1.311 (3)
C24—C25	1.384 (3)	O4—H4	0.8200
C24—H24A	0.9300	C8—C9	1.379 (3)
C17—C18	1.382 (3)	C8—H8A	0.9300
C17—H17A	0.9300	C5—C4	1.384 (3)
O10—C28	1.207 (3)	C5—H5A	0.9300
O9—C28	1.311 (3)	C9—H9A	0.9300
O9—H9	0.8200	C4—H4A	0.9300
C18—H18A	0.9300	C14—O1	1.408 (3)
C26—C25	1.375 (3)	C14—H14A	0.9700
C26—C30	1.501 (3)	C14—H14B	0.9700
C25—H25A	0.9300	C13—H13A	0.9600
C29—H29A	0.9600	C13—H13B	0.9600
C29—H29B	0.9600	C13—H13C	0.9600
C29—H29C	0.9600	O6—C30	1.409 (3)
O3—C7	1.379 (3)	O6—H6	0.8200
O3—C1	1.393 (2)	O1—H1	0.8200
C7—C12	1.376 (3)	C30—H30A	0.9700
C7—C8	1.378 (3)	C30—H30B	0.9700
C16—O8—C22	117.53 (13)	O3—C1—C6	119.31 (19)
C23—O7—C29	117.67 (17)	C7—C12—C11	119.26 (18)
C27—C22—C23	121.00 (18)	C7—C12—H12A	120.4
C27—C22—O8	119.45 (18)	C11—C12—H12A	120.4
C23—C22—O8	119.49 (17)	C9—C10—C11	119.3 (2)
C17—C16—O8	123.43 (17)	C9—C10—C15	119.11 (19)
C17—C16—C21	120.64 (18)	C11—C10—C15	121.6 (2)
O8—C16—C21	115.91 (16)	C12—C11—C10	120.4 (2)
C18—C19—C20	118.90 (18)	C12—C11—H11A	119.8
C18—C19—C28	122.14 (18)	C10—C11—H11A	119.8
C20—C19—C28	118.92 (18)	C4—C3—C2	117.9 (2)
C21—C20—C19	120.65 (18)	C4—C3—C14	121.1 (2)
C21—C20—H20A	119.7	C2—C3—C14	120.9 (2)
C19—C20—H20A	119.7	O2—C6—C5	125.7 (2)
O7—C23—C24	125.23 (19)	O2—C6—C1	115.72 (19)
O7—C23—C22	116.22 (16)	C5—C6—C1	118.6 (2)
C24—C23—C22	118.54 (19)	C1—C2—C3	120.8 (2)
C20—C21—C16	119.57 (18)	C1—C2—H2A	119.6
C20—C21—H21A	120.2	C3—C2—H2A	119.6
C16—C21—H21A	120.2	C15—O4—H4	109.5
C22—C27—C26	120.5 (2)	C7—C8—C9	119.3 (2)
C22—C27—H27A	119.7	C7—C8—H8A	120.3
C26—C27—H27A	119.7	C9—C8—H8A	120.3
C23—C24—C25	119.8 (2)	O5—C15—O4	123.3 (2)
C23—C24—H24A	120.1	O5—C15—C10	122.5 (2)
C25—C24—H24A	120.1	O4—C15—C10	114.19 (19)
C16—C17—C18	119.21 (18)	C6—C5—C4	119.6 (2)
C16—C17—H17A	120.4	C6—C5—H5A	120.2
C18—C17—H17A	120.4	C4—C5—H5A	120.2
C28—O9—H9	109.5	C8—C9—C10	120.6 (2)
C19—C18—C17	120.98 (18)	C8—C9—H9A	119.7
C19—C18—H18A	119.5	C10—C9—H9A	119.7
C17—C18—H18A	119.5	C3—C4—C5	122.0 (2)
C25—C26—C27	118.34 (19)	C3—C4—H4A	119.0
C25—C26—C30	120.8 (2)	C5—C4—H4A	119.0
C27—C26—C30	120.7 (2)	O1—C14—C3	108.56 (18)
C26—C25—C24	121.80 (19)	O1—C14—H14A	110.0
C26—C25—H25A	119.1	C3—C14—H14A	110.0
C24—C25—H25A	119.1	O1—C14—H14B	110.0
O10—C28—O9	122.3 (2)	C3—C14—H14B	110.0
O10—C28—C19	123.6 (2)	H14A—C14—H14B	108.4
O9—C28—C19	113.99 (19)	O2—C13—H13A	109.5
O7—C29—H29A	109.5	O2—C13—H13B	109.5
O7—C29—H29B	109.5	H13A—C13—H13B	109.5
H29A—C29—H29B	109.5	O2—C13—H13C	109.5
O7—C29—H29C	109.5	H13A—C13—H13C	109.5
H29A—C29—H29C	109.5	H13B—C13—H13C	109.5
H29B—C29—H29C	109.5	C30—O6—H6	109.5
C7—O3—C1	118.79 (15)	C14—O1—H1	109.5
C12—C7—C8	121.1 (2)	O6—C30—C26	109.97 (19)
C12—C7—O3	123.66 (18)	O6—C30—H30A	109.7
C8—C7—O3	115.18 (19)	C26—C30—H30A	109.7
C6—O2—C13	117.22 (18)	O6—C30—H30B	109.7
C2—C1—O3	119.55 (19)	C26—C30—H30B	109.7
C2—C1—C6	121.01 (19)	H30A—C30—H30B	108.2
C16—O8—C22—C27	109.7 (2)	C7—O3—C1—C2	−109.8 (2)
C16—O8—C22—C23	−73.2 (2)	C7—O3—C1—C6	74.4 (2)
C22—O8—C16—C17	−24.5 (3)	C8—C7—C12—C11	−0.2 (3)
C22—O8—C16—C21	156.97 (17)	O3—C7—C12—C11	178.08 (18)
C18—C19—C20—C21	−1.2 (3)	C7—C12—C11—C10	0.8 (3)
C28—C19—C20—C21	176.59 (19)	C9—C10—C11—C12	−0.7 (3)
C29—O7—C23—C24	3.4 (3)	C15—C10—C11—C12	178.07 (18)
C29—O7—C23—C22	−177.65 (19)	C13—O2—C6—C5	5.0 (3)
C27—C22—C23—O7	−178.58 (17)	C13—O2—C6—C1	−174.72 (19)
O8—C22—C23—O7	4.4 (3)	C2—C1—C6—O2	−179.12 (18)
C27—C22—C23—C24	0.5 (3)	O3—C1—C6—O2	−3.4 (3)
O8—C22—C23—C24	−176.58 (17)	C2—C1—C6—C5	1.1 (3)
C19—C20—C21—C16	−0.7 (3)	O3—C1—C6—C5	176.89 (18)
C17—C16—C21—C20	2.4 (3)	O3—C1—C2—C3	−176.70 (18)
O8—C16—C21—C20	−179.01 (16)	C6—C1—C2—C3	−1.0 (3)
C23—C22—C27—C26	−0.7 (3)	C4—C3—C2—C1	0.2 (3)
O8—C22—C27—C26	176.39 (17)	C14—C3—C2—C1	−177.01 (18)
O7—C23—C24—C25	178.76 (19)	C12—C7—C8—C9	−0.3 (3)
C22—C23—C24—C25	−0.2 (3)	O3—C7—C8—C9	−178.76 (19)
O8—C16—C17—C18	179.35 (18)	C9—C10—C15—O5	8.9 (3)
C21—C16—C17—C18	−2.2 (3)	C11—C10—C15—O5	−169.9 (2)
C20—C19—C18—C17	1.4 (3)	C9—C10—C15—O4	−170.1 (2)
C28—C19—C18—C17	−176.28 (19)	C11—C10—C15—O4	11.1 (3)
C16—C17—C18—C19	0.2 (3)	O2—C6—C5—C4	179.73 (18)
C22—C27—C26—C25	0.6 (3)	C1—C6—C5—C4	−0.6 (3)
C22—C27—C26—C30	176.53 (19)	C7—C8—C9—C10	0.3 (3)
C27—C26—C25—C24	−0.3 (3)	C11—C10—C9—C8	0.2 (3)
C30—C26—C25—C24	−176.3 (2)	C15—C10—C9—C8	−178.65 (19)
C23—C24—C25—C26	0.1 (3)	C2—C3—C4—C5	0.4 (3)
C18—C19—C28—O10	170.7 (2)	C14—C3—C4—C5	177.58 (19)
C20—C19—C28—O10	−7.0 (4)	C6—C5—C4—C3	−0.2 (3)
C18—C19—C28—O9	−6.9 (3)	C4—C3—C14—O1	−91.9 (3)
C20—C19—C28—O9	175.4 (2)	C2—C3—C14—O1	85.2 (3)
C1—O3—C7—C12	11.8 (3)	C25—C26—C30—O6	87.2 (3)
C1—O3—C7—C8	−169.74 (19)	C27—C26—C30—O6	−88.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9···O1	0.82	1.80	2.620 (2)	175
O4—H4···O6	0.82	1.84	2.652 (2)	1670
O6—H6···O10i	0.82	2.01	2.791 (3)	159
O1—H1···O5ii	0.82	1.89	2.706 (2)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9⋯O1	0.82	1.80	2.620 (2)	175
O4—H4⋯O6	0.82	1.84	2.652 (2)	1670
O6—H6⋯O10i	0.82	2.01	2.791 (3)	159
O1—H1⋯O5ii	0.82	1.89	2.706 (2)	172

Symmetry codes: (i) ; (ii) .