2-[1-(2-Hydr-oxy-3-methoxy-benz-yl)-1H-benzimidazol-2-yl]-6-methoxy-phenol methanol 1.13-solvate.

In the main mol-ecule of the title compound, C(22)H(20)N(2)O(4)·1.13CH(4)O, the dihedral angles between the benzimidazole plane and the two benzene rings are 80.53 (10) and 82.76 (10)°. The solvent mol-ecules are disordered between three positions, with refined occupancies of 0.506 (13), 0.373 (13) and 0.249 (5). The crystal structure is stabilized by inter-molecular O-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds. The crystal studied was a merohedral twin [BASF ratio of 0.917 (1)/0.083 (1)].

Related literature

For related structures, see Al-Douh et al. (2006 ▶, 2009 ▶). For hydrogen-bond motifs, see Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C22H20N2O4·1.13CH4O

M = 412.53

Monoclinic,

a = 7.2451 (1) Å

b = 11.1482 (2) Å

c = 26.2046 (5) Å

β = 90.010 (1)°

V = 2116.54 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.27 × 0.15 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.976, T max = 0.988

18918 measured reflections

3940 independent reflections

3099 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.122

S = 1.09

3940 reflections

317 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011192/cv2535sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011192/cv2535Isup2.hkl

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

C22H20N2O4·1.13CH4O	F(000) = 873
Mr = 412.53	Dx = 1.295 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4846 reflections
a = 7.2451 (1) Å	θ = 2.9–26.4°
b = 11.1482 (2) Å	µ = 0.09 mm−1
c = 26.2046 (5) Å	T = 100 K
β = 90.010 (1)°	Block, colourless
V = 2116.54 (6) Å3	0.27 × 0.15 × 0.13 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3940 independent reflections
Radiation source: fine-focus sealed tube	3099 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.976, Tmax = 0.988	k = −12→13
18918 measured reflections	l = −31→28

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0415P)2 + 1.5448P] where P = (Fo2 + 2Fc2)/3
3940 reflections	(Δ/σ)max < 0.001
317 parameters	Δρmax = 0.28 e Å−3
1 restraint	Δρmin = −0.23 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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)
O1	0.0363 (2)	0.18739 (17)	0.00815 (6)	0.0272 (4)
H1	0.0385	0.1891	−0.0231	0.041*
O2	0.3146 (2)	0.15819 (18)	−0.05634 (6)	0.0346 (5)
O3	0.0521 (3)	−0.24674 (15)	0.09905 (6)	0.0282 (4)
H3	0.0664	−0.3196	0.0971	0.042*
O4	0.2424 (3)	−0.39894 (16)	0.15953 (8)	0.0437 (6)
N1	0.0259 (3)	0.31698 (18)	0.13518 (7)	0.0220 (5)
N2	−0.0044 (3)	0.11719 (17)	0.13178 (7)	0.0196 (5)
C1	−0.1122 (3)	0.2812 (2)	0.16904 (9)	0.0199 (5)
C2	−0.2243 (3)	0.3492 (2)	0.20124 (9)	0.0237 (6)
H2A	−0.2161	0.4324	0.2019	0.028*
C3	−0.3483 (3)	0.2886 (2)	0.23220 (9)	0.0253 (6)
H3A	−0.4232	0.3321	0.2543	0.030*
C4	−0.3634 (4)	0.1640 (2)	0.23092 (9)	0.0255 (6)
H4A	−0.4479	0.1264	0.2523	0.031*
C5	−0.2560 (3)	0.0947 (2)	0.19875 (9)	0.0229 (6)
H5A	−0.2666	0.0116	0.1977	0.027*
C6	−0.1313 (3)	0.1562 (2)	0.16799 (8)	0.0195 (5)
C7	0.0860 (3)	0.2171 (2)	0.11421 (9)	0.0198 (5)
C8	0.2427 (3)	0.2062 (2)	0.07811 (9)	0.0196 (5)
C9	0.2130 (3)	0.1894 (2)	0.02649 (9)	0.0202 (5)
C10	0.3634 (4)	0.1738 (2)	−0.00633 (9)	0.0233 (6)
C11	0.5417 (4)	0.1767 (2)	0.01214 (10)	0.0289 (6)
H11A	0.6411	0.1665	−0.0099	0.035*
C12	0.5715 (4)	0.1951 (3)	0.06398 (10)	0.0324 (7)
H12A	0.6913	0.1981	0.0766	0.039*
C13	0.4233 (3)	0.2090 (2)	0.09689 (10)	0.0281 (6)
H13A	0.4441	0.2203	0.1316	0.034*
C14	0.0209 (3)	−0.0061 (2)	0.11471 (9)	0.0203 (5)
H14A	0.0840	−0.0054	0.0821	0.024*
H14B	−0.0994	−0.0423	0.1095	0.024*
C15	0.1298 (3)	−0.0828 (2)	0.15162 (9)	0.0193 (5)
C16	0.1386 (3)	−0.2048 (2)	0.14165 (9)	0.0210 (5)
C17	0.2424 (4)	−0.2802 (2)	0.17332 (10)	0.0256 (6)
C18	0.3361 (4)	−0.2327 (2)	0.21462 (10)	0.0267 (6)
H18A	0.4048	−0.2825	0.2358	0.032*
C19	0.3274 (3)	−0.1111 (2)	0.22427 (10)	0.0263 (6)
H19A	0.3906	−0.0793	0.2520	0.032*
C20	0.2259 (3)	−0.0364 (2)	0.19313 (9)	0.0241 (6)
H20A	0.2217	0.0454	0.1999	0.029*
C21	0.4624 (5)	0.1568 (4)	−0.09260 (11)	0.0588 (11)
H21A	0.4126	0.1590	−0.1265	0.088*
H21B	0.5337	0.0849	−0.0883	0.088*
H21C	0.5400	0.2255	−0.0873	0.088*
C22	0.4019 (4)	−0.4674 (3)	0.17089 (12)	0.0399 (7)
H22A	0.5094	−0.4261	0.1587	0.060*
H22B	0.3931	−0.5443	0.1546	0.060*
H22C	0.4112	−0.4783	0.2071	0.060*
O5A	1.0245 (11)	0.5263 (4)	0.0733 (2)	0.034 (2)	0.506 (13)
H5A1	1.0285	0.4805	0.0978	0.051*	0.506 (13)
C23A	0.8593 (19)	0.5039 (7)	0.0444 (6)	0.082 (5)	0.506 (13)
H23A	0.8527	0.4203	0.0358	0.123*	0.506 (13)
H23B	0.8616	0.5507	0.0136	0.123*	0.506 (13)
H23C	0.7534	0.5257	0.0643	0.123*	0.506 (13)
O5B	0.9164 (17)	0.5416 (6)	0.0975 (4)	0.048 (4)	0.373 (13)
H5B	0.9997	0.4977	0.0874	0.072*	0.373 (13)
C23B	0.739 (3)	0.5162 (11)	0.0664 (4)	0.064 (4)	0.373 (13)
H23D	0.7633	0.4547	0.0417	0.096*	0.373 (13)
H23E	0.7007	0.5881	0.0493	0.096*	0.373 (13)
H23F	0.6429	0.4900	0.0891	0.096*	0.373 (13)
O5C	0.718 (2)	0.4931 (11)	0.0088 (4)	0.082 (4)	0.249 (5)
H5C	0.7138	0.4829	−0.0222	0.123*	0.249 (5)
C23C	0.537 (3)	0.5098 (15)	0.0278 (8)	0.092 (7)	0.249 (5)
H23G	0.4542	0.4569	0.0102	0.139*	0.249 (5)
H23H	0.5401	0.4894	0.0633	0.139*	0.249 (5)
H23I	0.4957	0.5911	0.0239	0.139*	0.249 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0169 (9)	0.0456 (11)	0.0192 (9)	−0.0011 (8)	0.0000 (7)	−0.0004 (8)
O2	0.0215 (10)	0.0621 (13)	0.0202 (9)	−0.0080 (9)	0.0070 (8)	−0.0083 (9)
O3	0.0329 (10)	0.0216 (9)	0.0302 (10)	0.0024 (8)	−0.0068 (8)	−0.0033 (7)
O4	0.0460 (13)	0.0217 (10)	0.0633 (14)	0.0073 (9)	−0.0233 (11)	−0.0015 (9)
N1	0.0227 (11)	0.0222 (11)	0.0212 (10)	−0.0008 (9)	0.0010 (9)	0.0005 (9)
N2	0.0197 (11)	0.0203 (11)	0.0188 (10)	0.0011 (9)	0.0016 (9)	0.0001 (8)
C1	0.0194 (12)	0.0224 (13)	0.0179 (11)	0.0008 (10)	−0.0033 (10)	−0.0011 (10)
C2	0.0222 (13)	0.0258 (14)	0.0231 (13)	0.0033 (11)	−0.0044 (11)	−0.0039 (11)
C3	0.0197 (13)	0.0343 (15)	0.0220 (12)	0.0064 (12)	0.0010 (11)	−0.0048 (11)
C4	0.0207 (13)	0.0348 (15)	0.0210 (12)	−0.0006 (12)	0.0027 (11)	0.0019 (11)
C5	0.0234 (13)	0.0231 (13)	0.0220 (12)	0.0017 (11)	0.0002 (11)	0.0036 (10)
C6	0.0175 (12)	0.0248 (13)	0.0163 (11)	0.0047 (11)	−0.0010 (10)	−0.0020 (10)
C7	0.0201 (13)	0.0212 (13)	0.0182 (11)	0.0015 (11)	−0.0030 (10)	0.0011 (10)
C8	0.0196 (12)	0.0187 (12)	0.0204 (12)	0.0006 (10)	0.0020 (10)	0.0009 (10)
C9	0.0157 (12)	0.0203 (13)	0.0246 (12)	0.0003 (10)	0.0002 (10)	0.0002 (10)
C10	0.0233 (13)	0.0258 (14)	0.0208 (12)	−0.0035 (11)	0.0013 (11)	−0.0023 (10)
C11	0.0192 (13)	0.0366 (16)	0.0310 (14)	0.0028 (12)	0.0064 (11)	−0.0009 (12)
C12	0.0162 (13)	0.0496 (18)	0.0314 (15)	0.0010 (13)	−0.0038 (12)	0.0039 (13)
C13	0.0231 (14)	0.0394 (16)	0.0219 (13)	0.0032 (12)	−0.0023 (11)	0.0013 (12)
C14	0.0204 (12)	0.0216 (13)	0.0188 (12)	0.0004 (11)	0.0014 (10)	−0.0003 (10)
C15	0.0154 (12)	0.0232 (13)	0.0194 (12)	−0.0001 (10)	0.0051 (10)	0.0002 (10)
C16	0.0170 (12)	0.0248 (13)	0.0212 (12)	−0.0005 (11)	0.0032 (10)	0.0004 (10)
C17	0.0237 (13)	0.0208 (13)	0.0324 (14)	−0.0007 (11)	−0.0003 (12)	0.0039 (11)
C18	0.0228 (14)	0.0280 (15)	0.0292 (14)	0.0028 (12)	−0.0023 (12)	0.0102 (11)
C19	0.0222 (14)	0.0315 (15)	0.0253 (13)	−0.0009 (12)	−0.0042 (11)	0.0013 (11)
C20	0.0215 (13)	0.0253 (14)	0.0254 (13)	−0.0003 (11)	0.0016 (11)	−0.0013 (11)
C21	0.0388 (19)	0.110 (3)	0.0275 (16)	−0.026 (2)	0.0169 (15)	−0.0232 (18)
C22	0.0440 (18)	0.0312 (16)	0.0445 (17)	0.0119 (14)	0.0048 (15)	0.0037 (13)
O5A	0.056 (4)	0.016 (2)	0.030 (3)	−0.007 (2)	−0.017 (3)	0.0041 (17)
C23A	0.108 (9)	0.024 (4)	0.114 (10)	−0.011 (5)	−0.075 (8)	0.012 (5)
O5B	0.064 (7)	0.024 (4)	0.056 (6)	−0.014 (4)	−0.034 (6)	0.011 (3)
C23B	0.109 (12)	0.044 (6)	0.039 (6)	−0.029 (7)	0.002 (7)	−0.010 (5)
O5C	0.125 (12)	0.067 (8)	0.053 (7)	−0.011 (8)	−0.017 (8)	0.022 (6)
C23C	0.090 (15)	0.050 (10)	0.137 (18)	−0.013 (10)	−0.052 (14)	0.043 (11)

O1—C9	1.367 (3)	C14—H14A	0.9700
O1—H1	0.8200	C14—H14B	0.9700
O2—C10	1.368 (3)	C15—C16	1.387 (3)
O2—C21	1.432 (3)	C15—C20	1.391 (3)
O3—C16	1.363 (3)	C16—C17	1.400 (4)
O3—H3	0.8200	C17—C18	1.383 (4)
O4—C17	1.372 (3)	C18—C19	1.380 (4)
O4—C22	1.416 (3)	C18—H18A	0.9300
N1—C7	1.316 (3)	C19—C20	1.379 (4)
N1—C1	1.396 (3)	C19—H19A	0.9300
N2—C7	1.371 (3)	C20—H20A	0.9300
N2—C6	1.391 (3)	C21—H21A	0.9600
N2—C14	1.457 (3)	C21—H21B	0.9600
C1—C2	1.395 (3)	C21—H21C	0.9600
C1—C6	1.401 (3)	C22—H22A	0.9600
C2—C3	1.386 (4)	C22—H22B	0.9600
C2—H2A	0.9300	C22—H22C	0.9600
C3—C4	1.394 (4)	O5A—C23A	1.439 (9)
C3—H3A	0.9300	O5A—H5A1	0.8200
C4—C5	1.383 (4)	C23A—H23A	0.9600
C4—H4A	0.9300	C23A—H23B	0.9600
C5—C6	1.392 (3)	C23A—H23C	0.9600
C5—H5A	0.9300	O5B—C23B	1.547 (16)
C7—C8	1.483 (3)	O5B—H5B	0.8200
C8—C9	1.382 (3)	C23B—H23D	0.9600
C8—C13	1.398 (4)	C23B—H23E	0.9600
C9—C10	1.400 (3)	C23B—H23F	0.9600
C10—C11	1.380 (4)	O5C—C23C	1.41 (2)
C11—C12	1.390 (4)	O5C—H5C	0.8200
C11—H11A	0.9300	C23C—C23Ci	1.57 (4)
C12—C13	1.386 (4)	C23C—H23G	0.9600
C12—H12A	0.9300	C23C—H23H	0.9597
C13—H13A	0.9300	C23C—H23I	0.9602
C14—C15	1.513 (3)
C9—O1—H1	109.5	C16—C15—C14	117.3 (2)
C10—O2—C21	116.3 (2)	C20—C15—C14	123.4 (2)
C16—O3—H3	109.5	O3—C16—C15	118.0 (2)
C17—O4—C22	117.7 (2)	O3—C16—C17	121.8 (2)
C7—N1—C1	105.1 (2)	C15—C16—C17	120.2 (2)
C7—N2—C6	106.90 (19)	O4—C17—C18	125.2 (2)
C7—N2—C14	127.1 (2)	O4—C17—C16	115.0 (2)
C6—N2—C14	126.0 (2)	C18—C17—C16	119.8 (2)
C2—C1—N1	130.3 (2)	C19—C18—C17	119.8 (2)
C2—C1—C6	119.7 (2)	C19—C18—H18A	120.1
N1—C1—C6	110.0 (2)	C17—C18—H18A	120.1
C3—C2—C1	117.8 (2)	C20—C19—C18	120.6 (2)
C3—C2—H2A	121.1	C20—C19—H19A	119.7
C1—C2—H2A	121.1	C18—C19—H19A	119.7
C2—C3—C4	121.5 (2)	C19—C20—C15	120.4 (2)
C2—C3—H3A	119.3	C19—C20—H20A	119.8
C4—C3—H3A	119.3	C15—C20—H20A	119.8
C5—C4—C3	121.8 (2)	O2—C21—H21A	109.5
C5—C4—H4A	119.1	O2—C21—H21B	109.5
C3—C4—H4A	119.1	H21A—C21—H21B	109.5
C4—C5—C6	116.3 (2)	O2—C21—H21C	109.5
C4—C5—H5A	121.8	H21A—C21—H21C	109.5
C6—C5—H5A	121.8	H21B—C21—H21C	109.5
N2—C6—C5	132.1 (2)	O4—C22—H22A	109.5
N2—C6—C1	105.0 (2)	O4—C22—H22B	109.5
C5—C6—C1	122.9 (2)	H22A—C22—H22B	109.5
N1—C7—N2	112.9 (2)	O4—C22—H22C	109.5
N1—C7—C8	126.1 (2)	H22A—C22—H22C	109.5
N2—C7—C8	120.9 (2)	H22B—C22—H22C	109.5
C9—C8—C13	119.5 (2)	O5A—C23A—H23A	109.5
C9—C8—C7	121.1 (2)	O5A—C23A—H23B	109.5
C13—C8—C7	119.4 (2)	H23A—C23A—H23B	109.5
O1—C9—C8	119.5 (2)	O5A—C23A—H23C	109.5
O1—C9—C10	120.7 (2)	H23A—C23A—H23C	109.5
C8—C9—C10	119.8 (2)	H23B—C23A—H23C	109.5
O2—C10—C11	125.5 (2)	C23B—O5B—H5B	109.5
O2—C10—C9	113.8 (2)	O5B—C23B—H23D	109.5
C11—C10—C9	120.7 (2)	O5B—C23B—H23E	109.5
C10—C11—C12	119.4 (2)	H23D—C23B—H23E	109.5
C10—C11—H11A	120.3	O5B—C23B—H23F	109.5
C12—C11—H11A	120.3	H23D—C23B—H23F	109.5
C13—C12—C11	120.3 (2)	H23E—C23B—H23F	109.5
C13—C12—H12A	119.8	O5B—C23B—H23H	151.5
C11—C12—H12A	119.8	H23D—C23B—H23H	89.8
C12—C13—C8	120.2 (2)	H23E—C23B—H23H	82.0
C12—C13—H13A	119.9	O5C—C23C—C23Ci	88 (2)
C8—C13—H13A	119.9	O5C—C23C—H23G	109.3
N2—C14—C15	113.7 (2)	O5C—C23C—H23H	106.9
N2—C14—H14A	108.8	C23Ci—C23C—H23H	151.2
C15—C14—H14A	108.8	H23G—C23C—H23H	109.5
N2—C14—H14B	108.8	O5C—C23C—H23I	112.2
C15—C14—H14B	108.8	C23Ci—C23C—H23I	85.8
H14A—C14—H14B	107.7	H23G—C23C—H23I	109.5
C16—C15—C20	119.2 (2)	H23H—C23C—H23I	109.5
C7—N1—C1—C2	−179.5 (2)	C21—O2—C10—C9	172.4 (3)
C7—N1—C1—C6	0.7 (3)	O1—C9—C10—O2	0.6 (3)
N1—C1—C2—C3	−178.3 (2)	C8—C9—C10—O2	−180.0 (2)
C6—C1—C2—C3	1.6 (3)	O1—C9—C10—C11	179.5 (2)
C1—C2—C3—C4	−0.9 (4)	C8—C9—C10—C11	−1.0 (4)
C2—C3—C4—C5	−0.1 (4)	O2—C10—C11—C12	179.0 (3)
C3—C4—C5—C6	0.4 (4)	C9—C10—C11—C12	0.2 (4)
C7—N2—C6—C5	−178.4 (3)	C10—C11—C12—C13	0.7 (4)
C14—N2—C6—C5	3.9 (4)	C11—C12—C13—C8	−0.8 (4)
C7—N2—C6—C1	1.5 (2)	C9—C8—C13—C12	0.0 (4)
C14—N2—C6—C1	−176.2 (2)	C7—C8—C13—C12	177.9 (2)
C4—C5—C6—N2	−179.8 (2)	C7—N2—C14—C15	104.5 (3)
C4—C5—C6—C1	0.3 (4)	C6—N2—C14—C15	−78.2 (3)
C2—C1—C6—N2	178.7 (2)	N2—C14—C15—C16	171.5 (2)
N1—C1—C6—N2	−1.4 (3)	N2—C14—C15—C20	−11.3 (3)
C2—C1—C6—C5	−1.4 (4)	C20—C15—C16—O3	−176.2 (2)
N1—C1—C6—C5	178.5 (2)	C14—C15—C16—O3	1.2 (3)
C1—N1—C7—N2	0.3 (3)	C20—C15—C16—C17	0.4 (3)
C1—N1—C7—C8	−175.3 (2)	C14—C15—C16—C17	177.8 (2)
C6—N2—C7—N1	−1.2 (3)	C22—O4—C17—C18	−30.2 (4)
C14—N2—C7—N1	176.5 (2)	C22—O4—C17—C16	149.2 (2)
C6—N2—C7—C8	174.7 (2)	O3—C16—C17—O4	−3.0 (3)
C14—N2—C7—C8	−7.6 (4)	C15—C16—C17—O4	−179.5 (2)
N1—C7—C8—C9	−104.0 (3)	O3—C16—C17—C18	176.5 (2)
N2—C7—C8—C9	80.6 (3)	C15—C16—C17—C18	0.0 (4)
N1—C7—C8—C13	78.1 (3)	O4—C17—C18—C19	179.2 (2)
N2—C7—C8—C13	−97.3 (3)	C16—C17—C18—C19	−0.3 (4)
C13—C8—C9—O1	−179.6 (2)	C17—C18—C19—C20	0.1 (4)
C7—C8—C9—O1	2.5 (4)	C18—C19—C20—C15	0.4 (4)
C13—C8—C9—C10	0.9 (4)	C16—C15—C20—C19	−0.6 (3)
C7—C8—C9—C10	−177.0 (2)	C14—C15—C20—C19	−177.8 (2)
C21—O2—C10—C11	−6.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	2.21	2.651 (2)	114
O3—H3···O4	0.82	2.25	2.700 (3)	114
O3—H3···O5Aii	0.82	1.85	2.626 (5)	157
O5A—H5A1···N1iii	0.82	2.07	2.842 (5)	157
O1—H1···O3iv	0.82	2.19	2.956 (2)	155
C14—H14B···O2iv	0.97	2.46	3.335 (3)	150
C23A—H23B···O5Av	0.96	2.57	3.215 (16)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O5Ai	0.82	1.85	2.626 (5)	157
O5A—H5A1⋯N1ii	0.82	2.07	2.842 (5)	157
O1—H1⋯O3iii	0.82	2.19	2.956 (2)	155
C14—H14B⋯O2iii	0.97	2.46	3.335 (3)	150
C23A—H23B⋯O5Aiv	0.96	2.57	3.215 (16)	125

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