Synthesis and crystal structures of two purpurin derivatives: 1,4-dihy­droxy-2-propoxyanthra­quinone and 2-but­oxy-1,4-di­hydroxy­anthra­quinone

The title compounds were obtained by deprotonation of 1,2,4-tri­hydroxy­anthra­quinone (purpurin) using sodium hydride followed by reaction with either 1-bromo­propane or 1-bromo­butane. 1,4-Dihy­droxy-2-propoxyanthra­quinone crystallizes as a 1:1 solvate from aceto­nitrile, C₁₇H₁₄O₅·CH₃CN. The anthra­quinone core of the mol­ecule is essentially planar and both hy­droxy groups participate in intra­molecular O—H...O (carbon­yl) hydrogen bonds. The propyl chain is angled slightly above the plane of the anthra­quinone moiety with a maximum deviation of 0.247 (2) Å above the plane for the terminal carbon atom. In contrast, 2-but­oxy-1,4-di­hydroxy­anthra­quinone, C₁₈H₁₆O₅, crystallizes from nitro­methane with two independent mol­ecules in the asymmetric unit. The anthra­quinone core of each independent mol­ecule is essentially planar and both hy­droxy groups on both mol­ecules participate in intra­molecular O—H...O(carbon­yl) hydrogen bonds. The butyl chain in one mol­ecule is also angled slightly above the plane of the anthra­quinone moiety, with a maximum deviation of 0.833 (5) Å above the plane for the terminal carbon atom. In contrast, the butyl group on the second mol­ecule is twisted out of the plane of the anthra­quinone core with a torsion angle of 65.1 (3)°, resulting in a maximum deviation of 1.631 (5) Å above the plane for the terminal carbon atom.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.052
• wR factor = 0.153
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.68 Report
PLAT097_ALERT_2_C Large Reported Max.  (Positive) Residual Density       0.71 eA-3
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10    ..  N1      ..       2.73 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C5     -C14           1.45 Ang.
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C2 H3 N
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          6 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 2


Alert level B
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          2 Check

Author Response: (Iobs-Icalc)/SigmaW is 12.91 and 10.60 for reflections 2 13 4 and 2 14 4 respectively. There is, however, no reason to omit these two reflections.

Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00403 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C18 H16 O5
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      9.430 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.329 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          8 Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          4 Report
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C5     -C14           1.45 Ang.
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C23    -C32           1.45 Ang.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          4 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         21 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: SMART (Bruker, 2014); cell refinement: SMART (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: X-SEED (Barbour, 2001).

1,4-Dihydroxy-2-propoxyanthraquinone acetonitrile monosolvate (1)

Crystal data

C17H14O5·C2H3N	Z = 2
Mr = 339.33	F(000) = 356
Triclinic, P1	Dx = 1.425 Mg m^−3
a = 8.2160 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8605 (13) Å	Cell parameters from 3016 reflections
c = 10.7410 (14) Å	θ = 2.7–27.2°
α = 95.999 (2)°	µ = 0.10 mm^−1
β = 90.181 (2)°	T = 100 K
γ = 113.774 (2)°	Cut irregular block, orange
V = 790.99 (18) Å^3	0.45 × 0.18 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer	3548 independent reflections
Radiation source: fine-focus sealed tube	2718 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.3660 pixels mm^-1	θmax = 27.3°, θmin = 1.9°
phi and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −12→12
Tmin = 0.869, Tmax = 1.000	l = −13→13
10216 measured reflections

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.153	w = 1/[σ^2(Fo^2) + (0.0962P)^2 + 0.0684P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3548 reflections	Δρmax = 0.71 e Å^−3
234 parameters	Δρmin = −0.27 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.93351 (13)	0.54640 (11)	0.31245 (9)	0.0224 (2)
H1O	0.943 (2)	0.6376 (15)	0.3329 (15)	0.027*
N1	0.69308 (19)	1.25060 (16)	0.93564 (13)	0.0376 (4)
C1	0.83016 (17)	0.46925 (15)	0.39909 (12)	0.0179 (3)
O2	0.85708 (12)	0.26110 (10)	0.29025 (9)	0.0216 (2)
C2	0.78580 (17)	0.31187 (15)	0.38774 (12)	0.0186 (3)
O3	0.50110 (13)	0.19718 (10)	0.64607 (9)	0.0231 (3)
H3O	0.471 (2)	0.2555 (17)	0.6993 (14)	0.028*
C3	0.67840 (17)	0.22550 (15)	0.47188 (12)	0.0190 (3)
H3	0.650425	0.121543	0.464073	0.023*
O4	0.48044 (13)	0.42907 (11)	0.76272 (9)	0.0236 (2)
C4	0.60915 (17)	0.28978 (15)	0.56995 (12)	0.0184 (3)
O5	0.90743 (13)	0.77360 (10)	0.43289 (9)	0.0237 (3)
C5	0.65148 (17)	0.44303 (14)	0.58446 (12)	0.0168 (3)
C6	0.58069 (17)	0.50732 (15)	0.68671 (12)	0.0186 (3)
C7	0.63155 (17)	0.67078 (15)	0.70039 (12)	0.0182 (3)
C8	0.57026 (18)	0.73660 (16)	0.80017 (12)	0.0215 (3)
H8	0.496307	0.676508	0.858499	0.026*
C9	0.61668 (18)	0.88946 (16)	0.81480 (13)	0.0230 (3)
H9	0.577257	0.934122	0.884204	0.028*
C10	0.72114 (18)	0.97713 (15)	0.72752 (13)	0.0232 (3)
H10	0.750414	1.081320	0.736488	0.028*
C11	0.78274 (18)	0.91324 (15)	0.62752 (13)	0.0211 (3)
H11	0.854261	0.973685	0.568420	0.025*
C12	0.73939 (17)	0.75953 (14)	0.61376 (12)	0.0175 (3)
C13	0.80994 (17)	0.69324 (15)	0.50858 (12)	0.0185 (3)
C14	0.76399 (17)	0.53320 (14)	0.49710 (12)	0.0171 (3)
C15	0.80376 (18)	0.10079 (14)	0.26995 (12)	0.0197 (3)
H15A	0.672284	0.048972	0.262662	0.024*
H15B	0.847744	0.066928	0.341400	0.024*
C16	0.88231 (18)	0.06548 (15)	0.15066 (12)	0.0216 (3)
H16A	1.013724	0.117694	0.158502	0.026*
H16B	0.839009	0.100713	0.079785	0.026*
C17	0.8285 (2)	−0.10258 (15)	0.12525 (13)	0.0259 (3)
H17A	0.864454	−0.138135	0.198037	0.039*
H17B	0.887518	−0.124293	0.051405	0.039*
H17C	0.699127	−0.153202	0.110002	0.039*
C18	0.7439 (2)	1.37684 (18)	0.95263 (14)	0.0300 (3)
C19	0.8085 (2)	1.53842 (19)	0.97699 (19)	0.0451 (5)
H19A	0.707605	1.567300	0.974361	0.068*
H19B	0.891236	1.584642	0.913041	0.068*
H19C	0.870055	1.572114	1.059963	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0257 (5)	0.0171 (5)	0.0230 (5)	0.0076 (4)	0.0075 (4)	0.0008 (4)
N1	0.0451 (8)	0.0342 (8)	0.0356 (8)	0.0199 (7)	0.0016 (6)	−0.0023 (6)
C1	0.0159 (6)	0.0174 (6)	0.0186 (6)	0.0052 (5)	0.0005 (5)	0.0013 (5)
O2	0.0243 (5)	0.0157 (5)	0.0244 (5)	0.0086 (4)	0.0078 (4)	−0.0012 (4)
C2	0.0173 (6)	0.0200 (7)	0.0190 (6)	0.0092 (5)	0.0005 (5)	−0.0026 (5)
O3	0.0278 (5)	0.0164 (5)	0.0249 (5)	0.0086 (4)	0.0091 (4)	0.0029 (4)
C3	0.0188 (6)	0.0151 (6)	0.0230 (7)	0.0071 (5)	0.0002 (5)	0.0003 (5)
O4	0.0263 (5)	0.0202 (5)	0.0239 (5)	0.0092 (4)	0.0069 (4)	0.0018 (4)
C4	0.0176 (6)	0.0184 (6)	0.0194 (6)	0.0076 (5)	0.0011 (5)	0.0021 (5)
O5	0.0271 (5)	0.0170 (5)	0.0247 (5)	0.0066 (4)	0.0067 (4)	0.0018 (4)
C5	0.0165 (6)	0.0167 (6)	0.0170 (6)	0.0071 (5)	−0.0007 (5)	0.0000 (5)
C6	0.0178 (6)	0.0193 (7)	0.0193 (6)	0.0086 (5)	0.0004 (5)	0.0007 (5)
C7	0.0168 (6)	0.0182 (7)	0.0195 (6)	0.0078 (5)	−0.0019 (5)	−0.0012 (5)
C8	0.0225 (7)	0.0233 (7)	0.0192 (6)	0.0106 (6)	0.0007 (5)	−0.0004 (5)
C9	0.0228 (7)	0.0245 (7)	0.0230 (7)	0.0131 (6)	−0.0025 (5)	−0.0056 (5)
C10	0.0235 (7)	0.0183 (7)	0.0282 (7)	0.0107 (6)	−0.0037 (6)	−0.0042 (5)
C11	0.0207 (7)	0.0189 (6)	0.0236 (7)	0.0084 (5)	−0.0014 (5)	0.0008 (5)
C12	0.0167 (6)	0.0173 (7)	0.0180 (6)	0.0073 (5)	−0.0029 (5)	−0.0018 (5)
C13	0.0175 (6)	0.0170 (7)	0.0201 (6)	0.0065 (5)	−0.0009 (5)	0.0006 (5)
C14	0.0161 (6)	0.0156 (7)	0.0185 (6)	0.0061 (5)	−0.0015 (5)	−0.0012 (5)
C15	0.0206 (7)	0.0139 (6)	0.0233 (7)	0.0065 (5)	0.0030 (5)	−0.0017 (5)
C16	0.0223 (7)	0.0212 (7)	0.0208 (7)	0.0089 (5)	0.0021 (5)	−0.0006 (5)
C17	0.0319 (8)	0.0222 (7)	0.0228 (7)	0.0113 (6)	0.0068 (6)	−0.0028 (5)
C18	0.0311 (8)	0.0349 (9)	0.0271 (7)	0.0178 (7)	−0.0004 (6)	−0.0015 (6)
C19	0.0445 (10)	0.0300 (9)	0.0596 (11)	0.0163 (8)	−0.0157 (9)	−0.0045 (8)

Geometric parameters (Å, º)

O1—C1	1.3410 (15)	C9—C10	1.392 (2)
O1—H1O	0.875 (13)	C9—H9	0.9500
N1—C18	1.136 (2)	C10—C11	1.3877 (19)
C1—C14	1.3938 (19)	C10—H10	0.9500
C1—C2	1.4353 (19)	C11—C12	1.4013 (18)
O2—C2	1.3493 (16)	C11—H11	0.9500
O2—C15	1.4516 (15)	C12—C13	1.4814 (19)
C2—C3	1.3714 (19)	C13—C14	1.4584 (19)
O3—C4	1.3407 (15)	C15—C16	1.5075 (18)
O3—H3O	0.874 (14)	C15—H15A	0.9900
C3—C4	1.4106 (18)	C15—H15B	0.9900
C3—H3	0.9500	C16—C17	1.5265 (18)
O4—C6	1.2505 (16)	C16—H16A	0.9900
C4—C5	1.3983 (18)	C16—H16B	0.9900
O5—C13	1.2480 (16)	C17—H17A	0.9800
C5—C14	1.4292 (19)	C17—H17B	0.9800
C5—C6	1.4498 (18)	C17—H17C	0.9800
C6—C7	1.4836 (18)	C18—C19	1.456 (2)
C7—C8	1.3947 (18)	C19—H19A	0.9800
C7—C12	1.4025 (18)	C19—H19B	0.9800
C8—C9	1.3887 (19)	C19—H19C	0.9800
C8—H8	0.9500
C1—O1—H1O	104.0 (11)	C12—C11—H11	120.0
O1—C1—C14	123.72 (12)	C11—C12—C7	119.64 (12)
O1—C1—C2	117.06 (11)	C11—C12—C13	119.48 (12)
C14—C1—C2	119.22 (12)	C7—C12—C13	120.88 (12)
C2—O2—C15	116.12 (10)	O5—C13—C14	121.35 (12)
O2—C2—C3	125.11 (12)	O5—C13—C12	120.31 (12)
O2—C2—C1	114.62 (12)	C14—C13—C12	118.33 (12)
C3—C2—C1	120.27 (12)	C1—C14—C5	120.48 (12)
C4—O3—H3O	104.0 (11)	C1—C14—C13	119.04 (12)
C2—C3—C4	120.53 (12)	C5—C14—C13	120.47 (12)
C2—C3—H3	119.7	O2—C15—C16	107.99 (10)
C4—C3—H3	119.7	O2—C15—H15A	110.1
O3—C4—C5	122.48 (11)	C16—C15—H15A	110.1
O3—C4—C3	116.90 (12)	O2—C15—H15B	110.1
C5—C4—C3	120.61 (12)	C16—C15—H15B	110.1
C4—C5—C14	118.88 (12)	H15A—C15—H15B	108.4
C4—C5—C6	119.80 (12)	C15—C16—C17	109.75 (11)
C14—C5—C6	121.32 (12)	C15—C16—H16A	109.7
O4—C6—C5	121.78 (12)	C17—C16—H16A	109.7
O4—C6—C7	120.05 (11)	C15—C16—H16B	109.7
C5—C6—C7	118.17 (12)	C17—C16—H16B	109.7
C8—C7—C12	119.70 (12)	H16A—C16—H16B	108.2
C8—C7—C6	119.52 (12)	C16—C17—H17A	109.5
C12—C7—C6	120.79 (12)	C16—C17—H17B	109.5
C9—C8—C7	120.41 (13)	H17A—C17—H17B	109.5
C9—C8—H8	119.8	C16—C17—H17C	109.5
C7—C8—H8	119.8	H17A—C17—H17C	109.5
C8—C9—C10	119.86 (12)	H17B—C17—H17C	109.5
C8—C9—H9	120.1	N1—C18—C19	178.89 (17)
C10—C9—H9	120.1	C18—C19—H19A	109.5
C11—C10—C9	120.40 (12)	C18—C19—H19B	109.5
C11—C10—H10	119.8	H19A—C19—H19B	109.5
C9—C10—H10	119.8	C18—C19—H19C	109.5
C10—C11—C12	119.97 (13)	H19A—C19—H19C	109.5
C10—C11—H11	120.0	H19B—C19—H19C	109.5
C15—O2—C2—C3	4.50 (19)	C9—C10—C11—C12	0.2 (2)
C15—O2—C2—C1	−175.30 (10)	C10—C11—C12—C7	0.9 (2)
O1—C1—C2—O2	0.80 (18)	C10—C11—C12—C13	−178.36 (11)
C14—C1—C2—O2	−179.69 (11)	C8—C7—C12—C11	−0.8 (2)
O1—C1—C2—C3	−179.01 (11)	C6—C7—C12—C11	178.81 (11)
C14—C1—C2—C3	0.5 (2)	C8—C7—C12—C13	178.54 (11)
O2—C2—C3—C4	−179.31 (12)	C6—C7—C12—C13	−1.9 (2)
C1—C2—C3—C4	0.5 (2)	C11—C12—C13—O5	0.1 (2)
C2—C3—C4—O3	178.11 (11)	C7—C12—C13—O5	−179.19 (11)
C2—C3—C4—C5	−1.2 (2)	C11—C12—C13—C14	179.48 (11)
O3—C4—C5—C14	−178.34 (11)	C7—C12—C13—C14	0.19 (19)
C3—C4—C5—C14	0.9 (2)	O1—C1—C14—C5	178.71 (11)
O3—C4—C5—C6	1.4 (2)	C2—C1—C14—C5	−0.8 (2)
C3—C4—C5—C6	−179.28 (11)	O1—C1—C14—C13	−0.8 (2)
C4—C5—C6—O4	−0.6 (2)	C2—C1—C14—C13	179.77 (11)
C14—C5—C6—O4	179.13 (11)	C4—C5—C14—C1	0.1 (2)
C4—C5—C6—C7	178.82 (11)	C6—C5—C14—C1	−179.73 (11)
C14—C5—C6—C7	−1.4 (2)	C4—C5—C14—C13	179.51 (11)
O4—C6—C7—C8	1.5 (2)	C6—C5—C14—C13	−0.3 (2)
C5—C6—C7—C8	−177.94 (11)	O5—C13—C14—C1	−0.3 (2)
O4—C6—C7—C12	−178.03 (11)	C12—C13—C14—C1	−179.62 (11)
C5—C6—C7—C12	2.49 (19)	O5—C13—C14—C5	−179.72 (11)
C12—C7—C8—C9	−0.6 (2)	C12—C13—C14—C5	0.91 (19)
C6—C7—C8—C9	179.85 (11)	C2—O2—C15—C16	174.51 (10)
C7—C8—C9—C10	1.7 (2)	O2—C15—C16—C17	−179.69 (10)
C8—C9—C10—C11	−1.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O5	0.88 (1)	1.75 (1)	2.5537 (13)	152 (2)
O3—H3O···O4	0.87 (1)	1.75 (1)	2.5578 (13)	153 (2)
C10—H10···N1	0.95	2.73	3.4009 (19)	128
C15—H15A···O3^i	0.99	2.57	3.2179 (16)	123
C11—H11···O5^ii	0.95	2.47	3.2446 (17)	138

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y+2, −z+1.

2-Butoxy-1,4-dihydroxyanthraquinone (2)

Crystal data

C18H16O5	F(000) = 1312
Mr = 312.31	Dx = 1.428 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.7730 (9) Å	Cell parameters from 2921 reflections
b = 44.272 (8) Å	θ = 2.4–23.8°
c = 13.807 (3) Å	µ = 0.10 mm^−1
β = 95.164 (2)°	T = 100 K
V = 2905.8 (9) Å^3	Cut irregular block, orange-red
Z = 8	0.48 × 0.10 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer	6456 independent reflections
Radiation source: fine-focus sealed tube	3747 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.104
Detector resolution: 8.3660 pixels mm^-1	θmax = 27.2°, θmin = 1.6°
phi and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −56→56
Tmin = 0.854, Tmax = 1.000	l = −17→17
36901 measured reflections

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.166	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 2.0816P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
6456 reflections	Δρmax = 0.26 e Å^−3
429 parameters	Δρmin = −0.27 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.3186 (4)	0.27290 (4)	0.38526 (14)	0.0341 (5)
H1O	−0.448 (5)	0.2616 (6)	0.359 (2)	0.041*
C1	−0.3234 (6)	0.29688 (6)	0.32535 (19)	0.0272 (6)
O2	0.0428 (4)	0.31529 (4)	0.43337 (13)	0.0312 (5)
C2	−0.1245 (6)	0.32043 (6)	0.3504 (2)	0.0275 (6)
O3	−0.2823 (4)	0.37359 (4)	0.15477 (15)	0.0350 (5)
H3O	−0.399 (6)	0.3708 (7)	0.1034 (17)	0.042*
C3	−0.1160 (6)	0.34561 (6)	0.2928 (2)	0.0287 (6)
H3	0.017152	0.361103	0.309821	0.034*
O4	−0.6827 (4)	0.35220 (4)	0.04208 (14)	0.0367 (5)
C4	−0.3032 (6)	0.34858 (6)	0.2089 (2)	0.0286 (6)
O5	−0.7188 (4)	0.25237 (4)	0.26716 (15)	0.0375 (5)
C5	−0.5023 (5)	0.32611 (6)	0.18344 (19)	0.0254 (6)
O6	0.7609 (4)	0.39771 (4)	0.48700 (15)	0.0355 (5)
H6O	0.636 (6)	0.3937 (7)	0.4395 (17)	0.043*
C6	−0.6920 (6)	0.32954 (6)	0.0958 (2)	0.0293 (6)
O7	1.1866 (4)	0.42067 (4)	0.59154 (14)	0.0367 (5)
C7	−0.9003 (5)	0.30521 (6)	0.07061 (19)	0.0266 (6)
O8	1.2269 (4)	0.50371 (4)	0.37289 (15)	0.0341 (5)
H8O	1.123 (6)	0.5094 (7)	0.3208 (16)	0.041*
C8	−1.0870 (6)	0.30801 (6)	−0.0124 (2)	0.0328 (7)
H8	−1.081236	0.325412	−0.052455	0.039*
O9	0.8632 (4)	0.50517 (4)	0.22553 (14)	0.0359 (5)
C9	−1.2818 (6)	0.28529 (7)	−0.0366 (2)	0.0349 (7)
H9	−1.410599	0.287331	−0.092840	0.042*
O10	0.4078 (4)	0.40025 (4)	0.33801 (14)	0.0346 (5)
C10	−1.2893 (6)	0.25958 (6)	0.0210 (2)	0.0340 (7)
H10	−1.419875	0.243897	0.003368	0.041*
C11	−1.1065 (6)	0.25689 (6)	0.1040 (2)	0.0321 (7)
H11	−1.114821	0.239564	0.144244	0.038*
C12	−0.9090 (6)	0.27958 (6)	0.12909 (19)	0.0274 (6)
C13	−0.7114 (6)	0.27581 (6)	0.2171 (2)	0.0286 (6)
C14	−0.5100 (5)	0.29996 (6)	0.2427 (2)	0.0264 (6)
C15	0.2386 (6)	0.33909 (6)	0.4653 (2)	0.0313 (6)
H15B	0.136313	0.358244	0.473426	0.038*
H15A	0.375876	0.342303	0.416602	0.038*
C16	0.3885 (6)	0.32930 (6)	0.5611 (2)	0.0339 (7)
H16A	0.538850	0.344065	0.580570	0.041*
H16B	0.479215	0.309504	0.552161	0.041*
C17	0.1962 (7)	0.32659 (7)	0.6425 (2)	0.0402 (7)
H17A	0.060155	0.310046	0.626768	0.048*
H17B	0.088094	0.345572	0.646233	0.048*
C18	0.3532 (8)	0.32039 (7)	0.7413 (2)	0.0488 (9)
H18A	0.475930	0.302797	0.736548	0.073*
H18B	0.217716	0.316330	0.788912	0.073*
H18C	0.467288	0.338036	0.761934	0.073*
C19	0.8649 (6)	0.42371 (6)	0.4540 (2)	0.0296 (6)
C20	1.0975 (6)	0.43683 (6)	0.5119 (2)	0.0301 (6)
C21	1.2100 (6)	0.46359 (6)	0.4840 (2)	0.0302 (6)
H21	1.362242	0.472501	0.522992	0.036*
C22	1.1009 (6)	0.47784 (6)	0.3981 (2)	0.0300 (6)
C23	0.8739 (6)	0.46552 (6)	0.3399 (2)	0.0278 (6)
C24	0.7634 (6)	0.48070 (6)	0.2524 (2)	0.0293 (6)
C25	0.5272 (6)	0.46627 (6)	0.1918 (2)	0.0300 (6)
C26	0.4175 (6)	0.48005 (7)	0.1061 (2)	0.0365 (7)
H26	0.489850	0.498971	0.087551	0.044*
C27	0.2030 (7)	0.46627 (7)	0.0475 (2)	0.0413 (8)
H27	0.132225	0.475545	−0.011761	0.050*
C28	0.0917 (6)	0.43906 (7)	0.0752 (2)	0.0394 (7)
H28	−0.057104	0.429841	0.035422	0.047*
C29	0.1970 (6)	0.42527 (6)	0.1608 (2)	0.0354 (7)
H29	0.120415	0.406580	0.179632	0.042*
C30	0.4146 (6)	0.43869 (6)	0.2195 (2)	0.0305 (6)
C31	0.5203 (6)	0.42406 (6)	0.3111 (2)	0.0296 (6)
C32	0.7571 (6)	0.43774 (6)	0.3698 (2)	0.0290 (6)
C33	1.4201 (6)	0.43232 (6)	0.6555 (2)	0.0354 (7)
H33A	1.359002	0.449853	0.692861	0.042*
H33B	1.575349	0.438816	0.617335	0.042*
C34	1.5157 (7)	0.40682 (7)	0.7235 (2)	0.0392 (7)
H34A	1.589349	0.390176	0.685154	0.047*
H34B	1.351732	0.398995	0.754780	0.047*
C35	1.7415 (7)	0.41641 (7)	0.8018 (2)	0.0449 (8)
H35A	1.663659	0.431719	0.844235	0.054*
H35B	1.900044	0.425732	0.771114	0.054*
C36	1.8488 (8)	0.38931 (8)	0.8632 (2)	0.0525 (9)
H36A	1.695632	0.381183	0.898166	0.079*
H36B	2.003713	0.395739	0.910094	0.079*
H36C	1.915812	0.373660	0.820721	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0317 (11)	0.0275 (11)	0.0412 (12)	−0.0051 (9)	−0.0072 (9)	0.0049 (9)
C1	0.0237 (14)	0.0243 (14)	0.0334 (15)	0.0016 (11)	0.0025 (12)	0.0025 (12)
O2	0.0262 (10)	0.0271 (10)	0.0389 (11)	−0.0023 (8)	−0.0038 (9)	−0.0001 (8)
C2	0.0236 (14)	0.0239 (14)	0.0350 (15)	0.0027 (11)	0.0020 (12)	−0.0028 (11)
O3	0.0343 (12)	0.0276 (11)	0.0423 (12)	−0.0038 (9)	−0.0007 (9)	0.0058 (9)
C3	0.0229 (14)	0.0232 (14)	0.0400 (16)	−0.0018 (11)	0.0033 (12)	−0.0031 (12)
O4	0.0353 (12)	0.0298 (11)	0.0446 (12)	0.0010 (9)	0.0009 (9)	0.0078 (9)
C4	0.0251 (15)	0.0226 (14)	0.0387 (16)	0.0024 (11)	0.0057 (12)	0.0020 (12)
O5	0.0347 (12)	0.0297 (11)	0.0464 (12)	−0.0070 (9)	−0.0060 (9)	0.0081 (9)
C5	0.0211 (14)	0.0233 (13)	0.0325 (15)	0.0019 (11)	0.0059 (11)	−0.0008 (11)
O6	0.0331 (12)	0.0261 (10)	0.0468 (13)	−0.0057 (9)	0.0015 (9)	0.0027 (9)
C6	0.0236 (14)	0.0279 (15)	0.0364 (16)	0.0066 (11)	0.0024 (12)	0.0021 (12)
O7	0.0321 (11)	0.0302 (11)	0.0467 (12)	−0.0039 (9)	−0.0022 (9)	0.0032 (9)
C7	0.0224 (14)	0.0272 (14)	0.0306 (15)	0.0048 (11)	0.0048 (12)	−0.0013 (11)
O8	0.0304 (11)	0.0261 (10)	0.0456 (12)	−0.0053 (9)	0.0028 (9)	0.0013 (9)
C8	0.0322 (16)	0.0337 (16)	0.0324 (16)	0.0068 (13)	0.0024 (13)	0.0022 (12)
O9	0.0342 (12)	0.0263 (11)	0.0474 (12)	−0.0037 (9)	0.0047 (9)	0.0027 (9)
C9	0.0273 (16)	0.0401 (17)	0.0360 (17)	0.0071 (13)	−0.0035 (13)	−0.0072 (13)
O10	0.0291 (11)	0.0263 (11)	0.0487 (12)	−0.0046 (8)	0.0049 (9)	−0.0003 (9)
C10	0.0279 (16)	0.0323 (16)	0.0411 (17)	−0.0001 (12)	−0.0006 (13)	−0.0099 (13)
C11	0.0292 (16)	0.0276 (15)	0.0394 (16)	−0.0003 (12)	0.0030 (13)	−0.0039 (12)
C12	0.0235 (14)	0.0266 (14)	0.0323 (15)	0.0036 (11)	0.0029 (12)	−0.0039 (12)
C13	0.0239 (14)	0.0282 (15)	0.0335 (15)	0.0013 (12)	0.0008 (12)	−0.0015 (12)
C14	0.0207 (13)	0.0232 (14)	0.0355 (15)	0.0006 (11)	0.0033 (11)	−0.0004 (11)
C15	0.0266 (15)	0.0225 (14)	0.0443 (17)	−0.0034 (11)	0.0009 (13)	−0.0019 (12)
C16	0.0295 (16)	0.0277 (15)	0.0427 (17)	−0.0001 (12)	−0.0065 (13)	−0.0047 (13)
C17	0.0374 (18)	0.0405 (18)	0.0415 (18)	0.0057 (14)	−0.0024 (14)	−0.0005 (14)
C18	0.061 (2)	0.0373 (19)	0.0463 (19)	0.0090 (16)	−0.0058 (17)	−0.0034 (15)
C19	0.0277 (15)	0.0196 (13)	0.0425 (17)	−0.0021 (11)	0.0083 (13)	−0.0014 (12)
C20	0.0263 (15)	0.0263 (14)	0.0382 (16)	0.0031 (12)	0.0058 (13)	−0.0011 (12)
C21	0.0243 (15)	0.0255 (14)	0.0412 (17)	−0.0009 (11)	0.0058 (13)	−0.0041 (12)
C22	0.0265 (15)	0.0216 (14)	0.0432 (17)	−0.0018 (11)	0.0107 (13)	−0.0056 (12)
C23	0.0235 (14)	0.0217 (14)	0.0386 (16)	0.0013 (11)	0.0058 (12)	−0.0025 (12)
C24	0.0236 (14)	0.0238 (14)	0.0413 (16)	0.0001 (11)	0.0069 (12)	−0.0037 (12)
C25	0.0247 (15)	0.0257 (14)	0.0404 (16)	0.0012 (11)	0.0064 (12)	−0.0027 (12)
C26	0.0330 (17)	0.0319 (16)	0.0445 (18)	−0.0002 (13)	0.0029 (14)	0.0034 (13)
C27	0.0371 (18)	0.0395 (18)	0.0462 (19)	0.0042 (14)	−0.0024 (15)	0.0013 (14)
C28	0.0311 (17)	0.0384 (17)	0.0475 (19)	0.0008 (13)	−0.0022 (14)	−0.0066 (14)
C29	0.0277 (16)	0.0303 (16)	0.0483 (18)	−0.0006 (12)	0.0049 (14)	−0.0055 (13)
C30	0.0240 (15)	0.0278 (15)	0.0401 (17)	0.0020 (11)	0.0055 (13)	−0.0051 (12)
C31	0.0250 (15)	0.0234 (14)	0.0416 (17)	0.0023 (11)	0.0095 (13)	−0.0047 (12)
C32	0.0227 (14)	0.0242 (14)	0.0405 (16)	0.0004 (11)	0.0059 (12)	−0.0039 (12)
C33	0.0313 (16)	0.0294 (15)	0.0446 (18)	−0.0043 (13)	−0.0009 (13)	−0.0040 (13)
C34	0.0383 (18)	0.0347 (17)	0.0440 (18)	0.0003 (14)	−0.0001 (14)	0.0010 (14)
C35	0.046 (2)	0.0380 (18)	0.0495 (19)	0.0035 (15)	−0.0053 (16)	−0.0038 (15)
C36	0.056 (2)	0.047 (2)	0.052 (2)	0.0065 (17)	−0.0088 (17)	−0.0009 (16)

Geometric parameters (Å, º)

O1—C1	1.345 (3)	C16—H16A	0.9900
O1—H1O	0.848 (18)	C16—H16B	0.9900
C1—C14	1.390 (4)	C17—C18	1.520 (4)
C1—C2	1.431 (4)	C17—H17A	0.9900
O2—C2	1.356 (3)	C17—H17B	0.9900
O2—C15	1.450 (3)	C18—H18A	0.9800
C2—C3	1.372 (4)	C18—H18B	0.9800
O3—C4	1.344 (3)	C18—H18C	0.9800
O3—H3O	0.870 (17)	C19—C32	1.377 (4)
C3—C4	1.404 (4)	C19—C20	1.432 (4)
C3—H3	0.9500	C20—C21	1.370 (4)
O4—C6	1.251 (3)	C21—C22	1.402 (4)
C4—C5	1.399 (4)	C21—H21	0.9500
O5—C13	1.249 (3)	C22—C23	1.400 (4)
C5—C14	1.420 (4)	C23—C32	1.426 (4)
C5—C6	1.453 (4)	C23—C24	1.441 (4)
O6—C19	1.349 (3)	C24—C25	1.486 (4)
O6—H6O	0.863 (18)	C25—C26	1.392 (4)
C6—C7	1.485 (4)	C25—C30	1.401 (4)
O7—C20	1.348 (3)	C26—C27	1.388 (4)
O7—C33	1.453 (3)	C26—H26	0.9500
C7—C8	1.393 (4)	C27—C28	1.384 (4)
C7—C12	1.396 (4)	C27—H27	0.9500
O8—C22	1.354 (3)	C28—C29	1.384 (4)
O8—H8O	0.874 (17)	C28—H28	0.9500
C8—C9	1.390 (4)	C29—C30	1.392 (4)
C8—H8	0.9500	C29—H29	0.9500
O9—C24	1.253 (3)	C30—C31	1.469 (4)
C9—C10	1.391 (4)	C31—C32	1.462 (4)
C9—H9	0.9500	C33—C34	1.512 (4)
O10—C31	1.254 (3)	C33—H33A	0.9900
C10—C11	1.381 (4)	C33—H33B	0.9900
C10—H10	0.9500	C34—C35	1.517 (4)
C11—C12	1.399 (4)	C34—H34A	0.9900
C11—H11	0.9500	C34—H34B	0.9900
C12—C13	1.479 (4)	C35—C36	1.531 (4)
C13—C14	1.460 (4)	C35—H35A	0.9900
C15—C16	1.510 (4)	C35—H35B	0.9900
C15—H15B	0.9900	C36—H36A	0.9800
C15—H15A	0.9900	C36—H36B	0.9800
C16—C17	1.518 (4)	C36—H36C	0.9800
C1—O1—H1O	103 (2)	C17—C18—H18C	109.5
O1—C1—C14	123.8 (2)	H18A—C18—H18C	109.5
O1—C1—C2	116.9 (2)	H18B—C18—H18C	109.5
C14—C1—C2	119.3 (2)	O6—C19—C32	123.3 (2)
C2—O2—C15	116.7 (2)	O6—C19—C20	116.6 (2)
O2—C2—C3	125.4 (2)	C32—C19—C20	120.1 (2)
O2—C2—C1	114.2 (2)	O7—C20—C21	125.8 (3)
C3—C2—C1	120.4 (2)	O7—C20—C19	114.4 (2)
C4—O3—H3O	105 (2)	C21—C20—C19	119.9 (3)
C2—C3—C4	120.3 (2)	C20—C21—C22	120.1 (3)
C2—C3—H3	119.9	C20—C21—H21	120.0
C4—C3—H3	119.9	C22—C21—H21	120.0
O3—C4—C5	121.9 (2)	O8—C22—C23	121.4 (3)
O3—C4—C3	117.5 (2)	O8—C22—C21	117.3 (2)
C5—C4—C3	120.5 (2)	C23—C22—C21	121.3 (2)
C4—C5—C14	119.2 (2)	C22—C23—C32	118.2 (2)
C4—C5—C6	119.6 (2)	C22—C23—C24	120.4 (2)
C14—C5—C6	121.2 (2)	C32—C23—C24	121.4 (2)
C19—O6—H6O	100 (2)	O9—C24—C23	122.1 (3)
O4—C6—C5	121.7 (2)	O9—C24—C25	119.7 (3)
O4—C6—C7	120.1 (2)	C23—C24—C25	118.2 (2)
C5—C6—C7	118.2 (2)	C26—C25—C30	119.3 (3)
C20—O7—C33	118.4 (2)	C26—C25—C24	119.9 (3)
C8—C7—C12	119.9 (3)	C30—C25—C24	120.8 (3)
C8—C7—C6	119.6 (2)	C27—C26—C25	120.3 (3)
C12—C7—C6	120.6 (2)	C27—C26—H26	119.8
C22—O8—H8O	103 (2)	C25—C26—H26	119.8
C9—C8—C7	119.9 (3)	C28—C27—C26	120.2 (3)
C9—C8—H8	120.1	C28—C27—H27	119.9
C7—C8—H8	120.1	C26—C27—H27	119.9
C8—C9—C10	120.4 (3)	C27—C28—C29	120.1 (3)
C8—C9—H9	119.8	C27—C28—H28	120.0
C10—C9—H9	119.8	C29—C28—H28	120.0
C11—C10—C9	119.9 (3)	C28—C29—C30	120.2 (3)
C11—C10—H10	120.1	C28—C29—H29	119.9
C9—C10—H10	120.1	C30—C29—H29	119.9
C10—C11—C12	120.3 (3)	C29—C30—C25	119.9 (3)
C10—C11—H11	119.9	C29—C30—C31	119.5 (3)
C12—C11—H11	119.9	C25—C30—C31	120.6 (3)
C7—C12—C11	119.7 (2)	O10—C31—C32	121.0 (3)
C7—C12—C13	121.1 (2)	O10—C31—C30	120.2 (2)
C11—C12—C13	119.2 (2)	C32—C31—C30	118.9 (2)
O5—C13—C14	121.7 (2)	C19—C32—C23	120.5 (2)
O5—C13—C12	120.0 (2)	C19—C32—C31	119.5 (2)
C14—C13—C12	118.2 (2)	C23—C32—C31	120.0 (2)
C1—C14—C5	120.3 (2)	O7—C33—C34	106.5 (2)
C1—C14—C13	119.1 (2)	O7—C33—H33A	110.4
C5—C14—C13	120.6 (2)	C34—C33—H33A	110.4
O2—C15—C16	107.4 (2)	O7—C33—H33B	110.4
O2—C15—H15B	110.2	C34—C33—H33B	110.4
C16—C15—H15B	110.2	H33A—C33—H33B	108.6
O2—C15—H15A	110.2	C33—C34—C35	112.9 (2)
C16—C15—H15A	110.2	C33—C34—H34A	109.0
H15B—C15—H15A	108.5	C35—C34—H34A	109.0
C15—C16—C17	113.7 (2)	C33—C34—H34B	109.0
C15—C16—H16A	108.8	C35—C34—H34B	109.0
C17—C16—H16A	108.8	H34A—C34—H34B	107.8
C15—C16—H16B	108.8	C34—C35—C36	110.9 (3)
C17—C16—H16B	108.8	C34—C35—H35A	109.5
H16A—C16—H16B	107.7	C36—C35—H35A	109.5
C16—C17—C18	113.3 (3)	C34—C35—H35B	109.5
C16—C17—H17A	108.9	C36—C35—H35B	109.5
C18—C17—H17A	108.9	H35A—C35—H35B	108.1
C16—C17—H17B	108.9	C35—C36—H36A	109.5
C18—C17—H17B	108.9	C35—C36—H36B	109.5
H17A—C17—H17B	107.7	H36A—C36—H36B	109.5
C17—C18—H18A	109.5	C35—C36—H36C	109.5
C17—C18—H18B	109.5	H36A—C36—H36C	109.5
H18A—C18—H18B	109.5	H36B—C36—H36C	109.5
C15—O2—C2—C3	2.6 (4)	C33—O7—C20—C21	0.9 (4)
C15—O2—C2—C1	−176.8 (2)	C33—O7—C20—C19	−179.4 (2)
O1—C1—C2—O2	−0.6 (3)	O6—C19—C20—O7	1.7 (4)
C14—C1—C2—O2	178.7 (2)	C32—C19—C20—O7	−178.9 (2)
O1—C1—C2—C3	179.9 (2)	O6—C19—C20—C21	−178.5 (2)
C14—C1—C2—C3	−0.7 (4)	C32—C19—C20—C21	0.8 (4)
O2—C2—C3—C4	−179.2 (2)	O7—C20—C21—C22	178.6 (3)
C1—C2—C3—C4	0.2 (4)	C19—C20—C21—C22	−1.1 (4)
C2—C3—C4—O3	−179.2 (2)	C20—C21—C22—O8	−177.9 (2)
C2—C3—C4—C5	0.6 (4)	C20—C21—C22—C23	1.0 (4)
O3—C4—C5—C14	178.8 (2)	O8—C22—C23—C32	178.2 (2)
C3—C4—C5—C14	−1.0 (4)	C21—C22—C23—C32	−0.7 (4)
O3—C4—C5—C6	0.4 (4)	O8—C22—C23—C24	−1.7 (4)
C3—C4—C5—C6	−179.4 (2)	C21—C22—C23—C24	179.4 (3)
C4—C5—C6—O4	−0.1 (4)	C22—C23—C24—O9	−0.4 (4)
C14—C5—C6—O4	−178.5 (3)	C32—C23—C24—O9	179.7 (3)
C4—C5—C6—C7	179.8 (2)	C22—C23—C24—C25	178.4 (3)
C14—C5—C6—C7	1.4 (4)	C32—C23—C24—C25	−1.5 (4)
O4—C6—C7—C8	−0.8 (4)	O9—C24—C25—C26	−0.3 (4)
C5—C6—C7—C8	179.3 (2)	C23—C24—C25—C26	−179.1 (3)
O4—C6—C7—C12	178.8 (3)	O9—C24—C25—C30	179.0 (3)
C5—C6—C7—C12	−1.0 (4)	C23—C24—C25—C30	0.2 (4)
C12—C7—C8—C9	0.1 (4)	C30—C25—C26—C27	−1.4 (4)
C6—C7—C8—C9	179.8 (3)	C24—C25—C26—C27	178.0 (3)
C7—C8—C9—C10	−0.8 (4)	C25—C26—C27—C28	1.6 (5)
C8—C9—C10—C11	1.5 (4)	C26—C27—C28—C29	−0.9 (5)
C9—C10—C11—C12	−1.6 (4)	C27—C28—C29—C30	0.1 (4)
C8—C7—C12—C11	−0.2 (4)	C28—C29—C30—C25	0.1 (4)
C6—C7—C12—C11	−179.9 (2)	C28—C29—C30—C31	178.8 (3)
C8—C7—C12—C13	179.3 (2)	C26—C25—C30—C29	0.6 (4)
C6—C7—C12—C13	−0.3 (4)	C24—C25—C30—C29	−178.8 (3)
C10—C11—C12—C7	1.0 (4)	C26—C25—C30—C31	−178.2 (3)
C10—C11—C12—C13	−178.6 (2)	C24—C25—C30—C31	2.5 (4)
C7—C12—C13—O5	−178.4 (3)	C29—C30—C31—O10	−2.8 (4)
C11—C12—C13—O5	1.2 (4)	C25—C30—C31—O10	176.0 (2)
C7—C12—C13—C14	1.3 (4)	C29—C30—C31—C32	177.3 (3)
C11—C12—C13—C14	−179.1 (2)	C25—C30—C31—C32	−3.9 (4)
O1—C1—C14—C5	179.7 (2)	O6—C19—C32—C23	178.8 (2)
C2—C1—C14—C5	0.4 (4)	C20—C19—C32—C23	−0.5 (4)
O1—C1—C14—C13	−1.0 (4)	O6—C19—C32—C31	−0.9 (4)
C2—C1—C14—C13	179.6 (2)	C20—C19—C32—C31	179.8 (2)
C4—C5—C14—C1	0.5 (4)	C22—C23—C32—C19	0.5 (4)
C6—C5—C14—C1	178.9 (2)	C24—C23—C32—C19	−179.6 (3)
C4—C5—C14—C13	−178.8 (2)	C22—C23—C32—C31	−179.9 (2)
C6—C5—C14—C13	−0.4 (4)	C24—C23—C32—C31	0.0 (4)
O5—C13—C14—C1	−0.6 (4)	O10—C31—C32—C19	2.4 (4)
C12—C13—C14—C1	179.7 (2)	C30—C31—C32—C19	−177.7 (2)
O5—C13—C14—C5	178.7 (3)	O10—C31—C32—C23	−177.2 (2)
C12—C13—C14—C5	−1.0 (4)	C30—C31—C32—C23	2.7 (4)
C2—O2—C15—C16	176.7 (2)	C20—O7—C33—C34	−167.3 (2)
O2—C15—C16—C17	−65.1 (3)	O7—C33—C34—C35	−174.3 (3)
C15—C16—C17—C18	−173.1 (2)	C33—C34—C35—C36	−175.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O5	0.85 (2)	1.78 (2)	2.564 (3)	153 (3)
O3—H3O···O4	0.87 (2)	1.74 (2)	2.536 (3)	151 (3)
O6—H6O···O10	0.86 (2)	1.72 (2)	2.542 (3)	158 (3)
O8—H8O···O9	0.87 (2)	1.73 (2)	2.554 (3)	155 (3)
C3—H3···O10	0.95	2.55	3.494 (3)	173
C29—H29···O3	0.95	2.41	3.231 (4)	144
C15—H15B···O6^i	0.99	2.52	3.485 (3)	164
C21—H21···O8^ii	0.95	2.55	3.502 (3)	180
C33—H33A···O9^iii	0.99	2.56	3.547 (4)	172

Symmetry codes: (i) x−1, y, z; (ii) −x+3, −y+1, −z+1; (iii) −x+2, −y+1, −z+1.