Clarithromycin monohydrate: a synchrotron X-ray powder study.

In the crystal structure of the title compound, clarithromycin (CAM) monohydrate, C(38)H(69)NO(13)·H(2)O, the water mol-ecule behaves as a proton donor and is hydrogen bonded to the hy-droxy O atom of the CAM cladinose ring. The hy-droxy O atom also behaves as a proton donor, forming an inter-molecular hydrogen bond with one of the hy-droxy groups of the 14-membered aglycone ring. The CAM mol-ecules are linked through these hydrogen bonds into chains running parallel to the c axis.

Related literature

For background to the title compound, see Avrutov et al. (2003 ▶); Noguchi, Fujiki et al. (2012 ▶). For information relating to the pharmaceutical properties of CAM, see: Yajima et al. (1999 ▶, 2002 ▶); Fujiki et al. (2011 ▶); Liu et al. (1999 ▶). For related structures, see: Noguchi, Miura et al. (2012 ▶; form I, anhydrate); Jin et al. (2011 ▶; form 0, ethanol solvate); Stephenson et al. (1997 ▶; form II, anhydrate); Liang & Yao (2008 ▶; form III, acetonitrile solvate); Parvez et al. (2000 ▶; hydro­chloride salt); Iwasaki et al. (1993 ▶; methanol solvate).

Experimental

Crystal data

C38H69NO13·H2O

M = 765.97

Orthorhombic,

a = 15.6999 (2) Å

b = 18.8817 (2) Å

c = 15.0267 (2) Å

V = 4454.53 (9) Å3

Z = 4

Synchrotron radiation, λ = 1.3000 Å

μ = 0.41 mm−1

T = 298 K

cylinder, 3.0 × 0.3 mm

Data collection

BL-19B2 Debye–Scherrer camera diffractometer

Specimen mounting: capilary

Data collection mode: transmission

Scan method: Stationary detector

2θfixed = 65

Refinement

R p = 0.038

R wp = 0.052

R exp = 0.016

R Bragg = 0.059

R(F) = 0.076

R(F 2) = 0.07617

χ2 = 11.020

6201 data points

188 parameters

96 restraints

H-atom parameters not refined

Data collection: local software (Osaka et al., 2010 ▶; Takata et al., 2002 ▶); cell refinement: EXPO2009 (Altomare et al., 2009 ▶) and RIETAN-FP (Izumi & Momma, 2007 ▶); data reduction: local software (Takata et al., 2002 ▶); program(s) used to solve structure: CCP4 (Collaborative Computational Project, Number 4, 1994 ▶); program(s) used to refine structure: CCP4, RIETAN-FP and Jmol (Hanson, 2010 ▶); molecular graphics: CCP4MG (McNicholas et al., 2011 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005090/hb6588sup1.cif

Rietveld powder data: contains datablock(s) I. DOI: 10.1107/S1600536812005090/hb6588Isup2.rtv

Supplementary material file. DOI: 10.1107/S1600536812005090/hb6588Isup3.cml

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

C38H69NO13·H2O	F(000) = 1672.00
Mr = 765.97	Dx = 1.142 Mg m−3
Orthorhombic, P212121	Synchrotron radiation, λ = 1.3000 Å
Hall symbol: P 2ac 2ab	µ = 0.41 mm−1
a = 15.6999 (2) Å	T = 298 K
b = 18.8817 (2) Å	Particle morphology: powder
c = 15.0267 (2) Å	white
V = 4454.53 (9) Å3	cylinder, 3.0 × 0.3 mm
Z = 4	Specimen preparation: Prepared at 298 K and 101 kPa

BL-19B2 Debye–Scherrer camera diffractometer	Data collection mode: transmission
Radiation source: synchrotron, SPring-8 BL19B2	Scan method: Stationary detector
Si(111) monochromator	2θfixed = 65
Specimen mounting: capilary

Least-squares matrix: selected elements only	Profile function: split pseudo-Voigt function
Rp = 0.038	188 parameters
Rwp = 0.052	96 restraints
Rexp = 0.016	0 constraints
RBragg = 0.059	H-atom parameters not refined
R(F) = 0.076	Weighting scheme based on measured s.u.'s 1/[Yi]
R(F2) = 0.07617	(Δ/σ)max = 0.011
χ2 = 11.020	Background function: Legendre polynomials
6201 data points

	x	y	z	Uiso*/Ueq
O1	0.024 (1)	0.1102 (8)	0.205 (1)	0.066 (5)*
C1	0.154 (2)	−0.074 (2)	0.101 (2)	0.066 (5)*
O2	0.108 (2)	0.1127 (9)	0.327 (1)	0.066 (5)*
C2	0.217 (3)	−0.007 (2)	−0.026 (1)	0.066 (5)*
O3	0.256 (1)	0.079 (1)	0.220 (2)	0.066 (5)*
C3	0.156 (1)	0.0568 (7)	0.095 (1)	0.066 (5)*
O4	0.051 (1)	0.356 (1)	0.609 (1)	0.066 (5)*
C4	0.168 (1)	0.065 (1)	0.197 (1)	0.066 (5)*
O5	0.166 (1)	0.286 (1)	0.638 (1)	0.066 (5)*
C5	0.107 (1)	0.119 (1)	0.236 (1)	0.066 (5)*
O6	0.089 (1)	0.239 (1)	0.8636 (9)	0.066 (5)*
C6	0.0191 (8)	0.1221 (7)	0.111 (1)	0.066 (5)*
O7	−0.0338 (9)	0.2408 (9)	0.740 (2)	0.066 (5)*
C7	0.064 (1)	0.062 (1)	0.068 (1)	0.066 (5)*
O8	−0.1207 (9)	0.122 (1)	0.670 (1)	0.066 (5)*
C8	−0.073 (1)	0.117 (1)	0.092 (2)	0.066 (5)*
O9	−0.032 (2)	0.210 (1)	0.484 (2)	0.066 (5)*
C9	0.079 (1)	0.176 (1)	0.374 (1)	0.066 (5)*
C10	0.150 (1)	0.221 (1)	0.422 (1)	0.066 (5)*
C11	0.236 (1)	0.213 (1)	0.372 (2)	0.066 (5)*
C12	0.121 (1)	0.297 (1)	0.419 (1)	0.066 (5)*
C13	0.165 (1)	0.341 (1)	0.495 (1)	0.066 (5)*
C14	0.170 (2)	0.420 (1)	0.473 (2)	0.066 (5)*
C15	0.118 (1)	0.329 (1)	0.586 (1)	0.066 (5)*
C16	0.1654 (9)	0.2915 (7)	0.737 (1)	0.066 (5)*
C17	0.133 (1)	0.3633 (7)	0.763 (1)	0.066 (5)*
C18	0.207 (2)	0.411 (1)	0.784 (3)	0.066 (5)*
C19	0.1174 (8)	0.2269 (6)	0.7706 (8)	0.066 (5)*
C20	0.179 (1)	0.1663 (7)	0.777 (2)	0.066 (5)*
C21	0.0398 (9)	0.205 (1)	0.709 (1)	0.066 (5)*
C22	0.0214 (9)	0.1267 (8)	0.708 (2)	0.066 (5)*
C23	−0.005 (2)	0.095 (2)	0.797 (2)	0.066 (5)*
C24	−0.0497 (8)	0.109 (1)	0.645 (1)	0.066 (5)*
C25	−0.028 (1)	0.0617 (8)	0.564 (1)	0.066 (5)*
C26	0.012 (2)	−0.008 (1)	0.599 (2)	0.066 (5)*
C27	0.036 (1)	0.095 (1)	0.502 (2)	0.066 (5)*
C28	0.003 (2)	0.1505 (9)	0.434 (1)	0.066 (5)*
C29	−0.060 (1)	0.113 (2)	0.371 (2)	0.066 (5)*
N1	0.198 (1)	−0.0086 (9)	0.071 (1)	0.066 (5)*
C30	−0.108 (2)	0.245 (2)	0.457 (3)	0.066 (5)*
C31	0.096 (1)	0.3798 (7)	0.282 (1)	0.066 (5)*
C32	0.147 (2)	0.4097 (8)	0.204 (2)	0.066 (5)*
C33	0.144 (2)	0.3696 (9)	0.113 (2)	0.066 (5)*
C34	0.181 (3)	0.418 (2)	0.044 (2)	0.066 (5)*
C35	0.259 (2)	0.288 (1)	0.164 (2)	0.066 (5)*
C36	0.050 (1)	0.355 (2)	0.089 (2)	0.066 (5)*
C37	0.0039 (9)	0.319 (2)	0.166 (2)	0.066 (5)*
C38	−0.088 (1)	0.309 (2)	0.147 (2)	0.066 (5)*
O10	0.148 (1)	0.326 (1)	0.322 (1)	0.066 (5)*
O11	0.189 (1)	0.301 (1)	0.109 (2)	0.066 (5)*
O12	0.040 (2)	0.310 (1)	0.013 (2)	0.066 (5)*
O13	0.013 (1)	0.357 (1)	0.251 (1)	0.066 (5)*
O14	−0.108 (2)	0.328 (1)	−0.069 (2)	0.066 (5)*
H1	0.18752	−0.11445	0.08465	0.066*
H2	0.14803	−0.0724	0.16457	0.066*
H3	0.09936	−0.07653	0.07354	0.066*
H4	0.16522	−0.00535	−0.0587	0.066*
H5	0.25191	0.03289	−0.03953	0.066*
H6	0.24771	−0.05005	−0.04139	0.066*
H7	0.18159	0.09522	0.06236	0.066*
H8	0.15338	0.02044	0.2234	0.066*
H9	0.12561	0.16482	0.21795	0.066*
H10	0.04357	0.16609	0.09204	0.066*
H11	0.06159	0.06938	0.00406	0.066*
H12	0.03573	0.01907	0.08252	0.066*
H13	−0.10242	0.15481	0.12278	0.066*
H14	−0.08217	0.12197	0.02935	0.066*
H15	−0.0944	0.07245	0.11207	0.066*
H16	0.05924	0.21174	0.33347	0.066*
H17	0.15866	0.20417	0.48194	0.066*
H18	0.22516	0.21423	0.30905	0.066*
H19	0.27191	0.25247	0.38771	0.066*
H20	0.26242	0.16985	0.38811	0.066*
H21	0.0607	0.30225	0.42837	0.066*
H22	0.22166	0.32306	0.50104	0.066*
H23	0.11338	0.43968	0.46883	0.066*
H24	0.20102	0.4445	0.51848	0.066*
H25	0.19835	0.42629	0.41672	0.066*
H26	0.22007	0.28954	0.76484	0.066*
H27	0.10026	0.38318	0.71559	0.066*
H28	0.09815	0.35908	0.81542	0.066*
H29	0.23905	0.41951	0.73017	0.066*
H30	0.18542	0.45621	0.8051	0.066*
H31	0.24274	0.39006	0.82833	0.066*
H32	0.14917	0.12451	0.79505	0.066*
H33	0.20586	0.15915	0.72105	0.066*
H34	0.22166	0.17769	0.8214	0.066*
H35	0.05522	0.21868	0.64964	0.066*
H36	0.07503	0.10624	0.6907	0.066*
H37	−0.06312	0.10794	0.80989	0.066*
H38	0.00025	0.0447	0.79565	0.066*
H39	0.03108	0.11387	0.8437	0.066*
H40	−0.08013	0.05386	0.53219	0.066*
H41	−0.02796	−0.03231	0.6374	0.066*
H42	0.02733	−0.03813	0.55089	0.066*
H43	0.06242	0.00286	0.63387	0.066*
H44	0.07815	0.118	0.53798	0.066*
H45	0.06197	0.05736	0.4687	0.066*
H46	−0.08548	0.14665	0.33188	0.066*
H47	−0.03038	0.07754	0.33667	0.066*
H48	−0.10369	0.09003	0.40568	0.066*
H49	−0.14675	0.21036	0.43356	0.066*
H50	−0.1328	0.26788	0.5073	0.066*
H51	−0.09414	0.27884	0.41213	0.066*
H52	0.08197	0.41389	0.32742	0.066*
H53	0.12529	0.457	0.19385	0.066*
H54	0.20452	0.41209	0.22314	0.066*
H55	0.24159	0.42459	0.05703	0.066*
H56	0.17631	0.39594	−0.01318	0.066*
H57	0.15325	0.46267	0.04479	0.066*
H58	0.24994	0.30659	0.22227	0.066*
H59	0.27045	0.23838	0.1669	0.066*
H60	0.30803	0.31141	0.13802	0.066*
H61	0.02618	0.40102	0.07467	0.066*
H62	0.03089	0.27317	0.17169	0.066*
H63	−0.09586	0.27116	0.10468	0.066*
H64	−0.11828	0.29764	0.20071	0.066*
H65	−0.11127	0.35198	0.12218	0.066*
H66	0.28701	0.06779	0.17828	0.066*
H67	0.04599	0.26422	0.86513	0.066*
H68	−0.07662	0.21661	0.73170	0.066*
H69	0.07204	0.27540	0.01797	0.066*
H70	−0.05854	0.31967	−0.03228	0.066*
H71	−0.09198	0.31147	−0.12651	0.066*

O1—C5	1.39 (2)	C5—H9	0.96
O1—C6	1.43 (2)	O6—H67	0.82
C1—N1	1.49 (4)	C6—H10	0.96
O2—C5	1.37 (2)	O7—H68	0.82
O2—C9	1.46 (3)	C7—H12	0.96
C2—N1	1.49 (2)	C7—H11	0.96
O3—C4	1.45 (2)	C8—H14	0.96
C3—N1	1.45 (2)	C8—H13	0.96
C3—C7	1.50 (2)	C8—H15	0.96
C3—C4	1.55 (2)	C9—H16	0.96
O4—C15	1.22 (2)	C10—H17	0.96
C4—C5	1.52 (2)	C11—H20	0.96
O5—C15	1.36 (2)	C11—H19	0.96
O5—C16	1.49 (2)	C11—H18	0.96
O6—C19	1.485 (18)	C12—H21	0.96
C6—C8	1.48 (2)	C13—H22	0.96
C6—C7	1.48 (2)	C14—H25	0.96
O7—C21	1.42 (2)	C14—H24	0.96
O8—C24	1.20 (2)	C14—H23	0.96
O9—C30	1.42 (4)	C16—H26	0.96
O9—C28	1.46 (3)	C17—H27	0.96
C9—C28	1.57 (3)	C17—H28	0.96
C9—C10	1.58 (2)	C18—H31	0.96
C10—C12	1.51 (3)	C18—H30	0.96
C10—C11	1.55 (3)	C18—H29	0.96
C12—C13	1.57 (2)	C20—H33	0.96
C13—C14	1.53 (3)	C20—H32	0.96
C13—C15	1.57 (2)	C20—H34	0.96
C16—C17	1.500 (19)	C21—H35	0.96
C16—C19	1.520 (18)	C22—H36	0.96
C17—C18	1.50 (3)	C23—H38	0.96
C19—C20	1.501 (19)	C23—H37	0.96
C19—C21	1.585 (19)	C23—H39	0.96
C21—C22	1.51 (2)	C25—H40	0.96
C22—C24	1.50 (3)	C26—H42	0.96
C22—C23	1.52 (4)	C26—H43	0.96
C24—C25	1.55 (2)	C26—H41	0.96
C25—C27	1.51 (3)	C27—H44	0.96
C25—C26	1.55 (3)	C27—H45	0.96
C27—C28	1.55 (3)	C29—H46	0.96
C28—C29	1.54 (4)	C29—H47	0.96
C31—O10	1.44 (2)	C29—H48	0.96
C31—O13	1.45 (2)	C30—H50	0.96
C31—C32	1.53 (3)	C30—H51	0.96
C32—C33	1.56 (4)	C30—H49	0.96
C33—O11	1.48 (3)	C31—H52	0.96
C33—C34	1.50 (4)	C32—H54	0.96
C33—C36	1.54 (4)	C32—H53	0.96
C35—O11	1.40 (4)	C34—H57	0.96
C36—O12	1.43 (4)	C34—H56	0.96
C36—C37	1.53 (4)	C34—H55	0.98
C37—O13	1.47 (4)	C35—H58	0.96
C37—C38	1.48 (2)	C35—H59	0.96
C1—H1	0.96	C35—H60	0.96
C1—H3	0.96	C36—H61	0.96
C1—H2	0.96	C37—H62	0.96
C2—H4	0.96	C38—H64	0.96
C2—H5	0.96	C38—H65	0.96
C2—H6	0.96	C38—H63	0.96
O3—H66	0.82	O12—H69	0.82
C3—H7	0.96	O14—H70	0.96
C4—H8	0.96	O14—H71	0.96
C5—O1—C6	111.2 (13)	H15—C8—C6	109.3
C5—O2—C9	114.0 (16)	C28—O9—H51	114.2
N1—C3—C7	115.3 (13)	H16—C9—O2	111.4
N1—C3—C4	106.0 (13)	H16—C9—C28	109.9
C7—C3—C4	112.1 (13)	H17—C10—C12	112.2
O3—C4—C5	112.8 (16)	H17—C10—C11	107.7
O3—C4—C3	111.7 (16)	H17—C10—C9	111.0
C5—C4—C3	111.8 (13)	C11—C10—H16	107.1
C15—O5—C16	122.0 (15)	H20—C11—H19	109.8
O2—C5—O1	109.5 (18)	H20—C11—H18	111.0
O2—C5—C4	108.6 (16)	H20—C11—C10	109.8
O1—C5—C4	112.4 (14)	H19—C11—H18	109.0
O1—C6—C8	103.5 (16)	H19—C11—C10	109.0
O1—C6—C7	106.5 (12)	H18—C11—C10	109.3
C8—C6—C7	109.3 (14)	H21—C12—C10	112.4
C6—C7—C3	112.9 (13)	H21—C12—C13	106.1
C30—O9—C28	122 (3)	H21—C12—O10	110.8
O2—C9—C28	105.3 (16)	H22—C13—C14	109.0
O2—C9—C10	116.2 (17)	H22—C13—C15	108.2
C28—C9—C10	116.1 (13)	H22—C13—C12	107.1
C12—C10—C11	109.9 (14)	H25—C14—H24	110.0
C12—C10—C9	106.6 (13)	H25—C14—H23	109.2
C11—C10—C9	109.9 (14)	H25—C14—C13	109.6
C10—C12—C13	110.4 (13)	H24—C14—H23	109.1
C10—C12—O10	105.7 (13)	H24—C14—C13	109.5
C13—C12—O10	111.2 (14)	H23—C14—C13	109.3
C14—C13—C15	110.7 (17)	H26—C16—O5	115.5
C14—C13—C12	112.4 (16)	H26—C16—C17	102.6
C15—C13—C12	110.5 (13)	H26—C16—C19	105.4
O4—C15—O5	124.5 (16)	H27—C17—H28	109.1
O4—C15—C13	126.3 (16)	H27—C17—C18	109.7
O5—C15—C13	109.1 (14)	H27—C17—C16	109.9
O5—C16—C17	109.0 (13)	H28—C17—C18	108.6
O5—C16—C19	106.2 (12)	H28—C17—C16	109.4
C17—C16—C19	118.1 (12)	H28—C17—H26	109.2
C18—C17—C16	109.5 (15)	H31—C18—H30	110.0
O6—C19—C20	104.5 (15)	H31—C18—H29	109.6
O6—C19—C16	109.8 (12)	H31—C18—C17	110.2
O6—C19—C21	111.0 (11)	H30—C18—H29	108.5
C20—C19—C16	108.3 (11)	H30—C18—C17	109.6
C20—C19—C21	109.5 (13)	H29—C18—C17	108.9
C16—C19—C21	113.4 (11)	C16—C19—H67	104.0
O7—C21—C22	108.4 (13)	H33—C20—H32	110.3
O7—C21—C19	108.1 (15)	H33—C20—H34	109.5
C22—C21—C19	114.2 (14)	H33—C20—C19	109.5
C24—C22—C21	111.6 (16)	H32—C20—H34	109.3
C24—C22—C23	105.3 (16)	H32—C20—C19	109.4
C21—C22—C23	115 (2)	H34—C20—C19	108.9
O8—C24—C22	116.6 (16)	H35—C21—O7	113.0
O8—C24—C25	124.6 (15)	H35—C21—C22	107.0
C22—C24—C25	117.4 (13)	H35—C21—C19	106.5
C27—C25—C24	113.1 (14)	H35—C21—H68	112.6
C27—C25—C26	107.1 (16)	H68—C21—H36	113.9
C24—C25—C26	108.2 (15)	H36—C22—C24	113.0
C25—C27—C28	117.8 (16)	H36—C22—C21	103.2
O9—C28—C29	115 (3)	H36—C22—C23	108.8
O9—C28—C27	107.9 (17)	H38—C23—H37	110.1
O9—C28—C9	110.2 (17)	H38—C23—H39	109.5
C29—C28—C27	108.0 (19)	H38—C23—C22	109.8
C29—C28—C9	106.0 (14)	H37—C23—H39	109.0
C27—C28—C9	109 (2)	H37—C23—C22	109.3
C3—N1—C2	108.6 (19)	H39—C23—C22	109.0
C3—N1—C1	115.0 (18)	H40—C25—C27	108.6
C2—N1—C1	114 (2)	H40—C25—C24	107.1
O10—C31—O13	115.8 (14)	H40—C25—C26	112.5
O10—C31—C32	106.6 (15)	H42—C26—H43	110.0
O13—C31—C32	109.5 (16)	H42—C26—H41	109.9
C31—C32—C33	118.4 (17)	H42—C26—C25	110.5
O11—C33—C34	109 (3)	H43—C26—H41	108.1
O11—C33—C36	107 (2)	H43—C26—C25	109.0
O11—C33—C32	117 (2)	H41—C26—C25	109.3
C34—C33—C36	109 (3)	H44—C27—H45	109.4
C34—C33—C32	107.3 (19)	H44—C27—C25	107.1
C36—C33—C32	109 (2)	H44—C27—C28	107.9
O12—C36—C37	107 (3)	H45—C27—C25	106.6
O12—C36—C33	113 (2)	H45—C27—C28	107.5
C37—C36—C33	111 (2)	H46—C29—H47	110.0
O13—C37—C38	109 (2)	H46—C29—H48	109.5
O13—C37—C36	113 (3)	H46—C29—C28	109.3
C38—C37—C36	112 (2)	H47—C29—H48	109.4
C31—O10—C12	118.0 (13)	H47—C29—C28	109.6
C35—O11—C33	120 (2)	H48—C29—C28	109.1
C31—O13—C37	120.7 (14)	H50—C30—H51	110.6
H1—C1—H3	110.1	H50—C30—H49	109.6
H1—C1—H2	109.6	H50—C30—O9	109.3
H1—C1—N1	109.5	H51—C30—H49	109.6
H3—C1—H2	109.5	H51—C30—O9	108.9
H3—C1—N1	109.3	H49—C30—O9	108.7
H2—C1—N1	108.8	H52—C31—O10	107.6
H4—C2—H5	110.2	H52—C31—O13	103.1
H4—C2—H6	109.0	H52—C31—C32	114.4
H4—C2—N1	110.3	H54—C32—H53	109.6
H5—C2—H6	108.4	H54—C32—C31	106.8
H5—C2—N1	110.0	H54—C32—C33	108.1
H6—C2—N1	108.8	H53—C32—C31	106.4
H66—O3—C4	110.0	H53—C32—C33	107.5
H66—O3—H8	111.6	H57—C34—H56	111.2
H7—C3—N1	108.6	H57—C34—H55	109.4
H7—C3—C7	102.0	H57—C34—C33	110.3
H7—C3—C4	112.3	H56—C34—H55	108.4
H8—C4—O3	106.6	H56—C34—C33	109.0
H8—C4—C5	106.2	H55—C34—C33	108.3
H8—C4—C3	107.4	H58—C35—H59	110.7
H8—C4—H66	108.7	H58—C35—H60	108.8
H9—C5—O2	110.6	H58—C35—O11	110.8
H9—C5—O1	106.9	H59—C35—H60	108.8
H9—C5—C4	107.9	H59—C35—O11	110.0
O1—C5—H8	101.8	H60—C35—O11	107.7
H67—O6—C19	111.0	H61—C36—O12	108.6
H10—C6—O1	114.5	H61—C36—C37	112.7
H10—C6—C8	112.5	H61—C36—C33	105.1
H10—C6—C7	109.4	H62—C37—O13	108.1
H68—O7—C21	110.8	H62—C37—C38	109.4
H68—O7—H35	110.4	H62—C37—C36	105.2
H12—C7—H11	109.5	H64—C38—H63	109.3
H12—C7—C6	109.0	H64—C38—H65	109.3
H12—C7—C3	108.7	H64—C38—C37	110.3
H11—C7—C6	108.5	H63—C38—H65	108.9
H11—C7—C3	108.6	H63—C38—C37	109.7
C6—C7—H7	103.0	H65—C38—C37	109.3
H14—C8—H13	109.6	C33—O11—H60	111.0
H14—C8—H15	109.5	H69—O12—C36	109.7
H14—C8—C6	109.5	C36—O12—H70	110.3
H13—C8—H15	109.5	C31—O13—H62	107.2
H13—C8—C6	109.4	H70—O14—H71	104.5

D—H···A	D—H	H···A	D···A	D—H···A
O6—H67···O7	0.83	2.30	2.68 (3)	108
O7—H68···O8	0.82	2.13	2.83 (3)	143
O12—H69···O11	0.83	2.34	2.75 (4)	111
O6—H67···O12i	0.83	2.39	2.73 (3)	105
O12—H69···O6ii	0.83	2.43	2.73 (3)	102
O14—H70···O12	0.97	1.70	2.65 (4)	168
O14—H71···O7ii	0.95	2.58	3.51 (4)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H67⋯O7	0.83	2.30	2.68 (3)	108
O7—H68⋯O8	0.82	2.13	2.83 (3)	143
O12—H69⋯O11	0.83	2.34	2.75 (4)	111
O6—H67⋯O12i	0.83	2.39	2.73 (3)	105
O12—H69⋯O6ii	0.83	2.43	2.73 (3)	102
O14—H70⋯O12	0.97	1.70	2.65 (4)	168
O14—H71⋯O7ii	0.95	2.58	3.51 (4)	166

Symmetry codes: (i) ; (ii) .