1,2-Bis­[bis(4-methoxy­phenyl)­hydroxy­methyl]­benzene

The title diol, C₃₆H₃₄O₆, has approximate twofold rotation symmetry in its crystal structure. It forms both intramolecular and intermolecular hydrogen bonds through its twofold disordered OH groups, linking most of the mol­ecules into pairs with a chain of three O—H...O hydrogen bonds. As a result of the disorder, these dimers have an average centrosymmetric structure, and 12 (3)% of the mol­ecules have only an intramolecular hydrogen bond, with no dimer formation.

Key indicators

• Single-crystal X-ray study
• T = 160 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.052
• wR factor = 0.132
• Data-to-parameter ratio = 13.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



PLAT_420  Alert B D-H Without Acceptor       O(1)   -  >H(1A)             ?

Author response: This feature of the hydrogen bonding is discussed in the paper; there is indeed no acceptor, this is genuine.

 Alert Level C:



RADNW_01  Alert C The radiation wavelength lies outside the expected range
          for the supplied radiation type. Expected range 1.54175-1.54180
          Wavelength given =    1.54184


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: DIF4 (Stoe & Cie, 1988); cell refinement: DIF4; data reduction: local programs; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

1,2-Bis[bis(4-methoxyphenyl)hydroxymethyl]benzene

Crystal data

C36H34O6	Z = 2
Mr = 562.63	F(000) = 596
Triclinic, P1	Dx = 1.263 Mg m^−3
a = 10.584 (3) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.437 (3) Å	Cell parameters from 47 reflections
c = 13.510 (3) Å	θ = 21.0–24.8°
α = 84.45 (2)°	µ = 0.69 mm^−1
β = 71.11 (2)°	T = 160 K
γ = 72.96 (2)°	Plate, colourless
V = 1479.4 (7) Å^3	0.36 × 0.22 × 0.04 mm

Data collection

Stoe–Siemens diffractometer	3615 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.083
Graphite monochromator	θmax = 67.7°, θmin = 3.5°
ω/θ scans with on–line profile fitting (Clegg, 1981)	h = −11→12
Absorption correction: ψ scan (XPREP in SHELXTL; Sheldrick, 2001)	k = −13→13
Tmin = 0.789, Tmax = 0.991	l = −9→16
5605 measured reflections	5 standard reflections every 60 min
5182 independent reflections	intensity decay: 2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.132	w = 1/[σ^2(Fo^2) + (0.0432P)^2 + 0.7787P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
5182 reflections	Δρmax = 0.19 e Å^−3
397 parameters	Δρmin = −0.21 e Å^−3
6 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (2)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.58621 (19)	0.79252 (18)	0.20172 (14)	0.0328 (4)
H1A	0.670 (3)	0.771 (5)	0.173 (4)	0.049*	0.56 (3)
H1B	0.561 (7)	0.836 (6)	0.157 (4)	0.049*	0.44 (3)
C1	0.5650 (2)	0.8683 (2)	0.28879 (18)	0.0259 (5)
C2	0.6680 (2)	0.9466 (2)	0.26358 (18)	0.0251 (5)
C3	0.7103 (2)	0.9648 (2)	0.34762 (19)	0.0289 (6)
H3	0.6771	0.9262	0.4125	0.035*
C4	0.7977 (2)	1.0360 (2)	0.3407 (2)	0.0321 (6)
H4	0.8257	1.0444	0.3991	0.039*
C5	0.8440 (3)	1.0946 (3)	0.2480 (2)	0.0350 (6)
H5	0.9034	1.1449	0.2418	0.042*
C6	0.8027 (3)	1.0794 (3)	0.1637 (2)	0.0336 (6)
H6	0.8357	1.1198	0.0998	0.040*
C7	0.7146 (2)	1.0070 (2)	0.16848 (18)	0.0265 (5)
C8	0.6895 (2)	0.9930 (2)	0.06353 (19)	0.0267 (5)
O2	0.54983 (19)	0.98519 (19)	0.08376 (15)	0.0341 (4)
H2A	0.547 (6)	0.918 (3)	0.107 (4)	0.051*	0.56 (3)
H2B	0.531 (8)	0.987 (7)	0.030 (4)	0.051*	0.44 (3)
C9	0.4155 (2)	0.9525 (2)	0.31778 (18)	0.0253 (5)
C10	0.3796 (3)	1.0668 (2)	0.36153 (19)	0.0301 (6)
H10	0.4506	1.0971	0.3689	0.036*
C11	0.2421 (3)	1.1386 (2)	0.3950 (2)	0.0331 (6)
H11	0.2201	1.2170	0.4245	0.040*
C12	0.1385 (2)	1.0951 (2)	0.3853 (2)	0.0314 (6)
C13	0.1725 (3)	0.9816 (2)	0.3404 (2)	0.0347 (6)
H13	0.1014	0.9519	0.3326	0.042*
C14	0.3094 (3)	0.9114 (2)	0.3070 (2)	0.0321 (6)
H14	0.3312	0.8338	0.2763	0.039*
O3	−0.00057 (18)	1.15607 (18)	0.41710 (16)	0.0444 (5)
C15	−0.0418 (3)	1.2668 (3)	0.4724 (3)	0.0634 (10)
H15A	−0.0124	1.2514	0.5353	0.095*
H15B	−0.1431	1.2995	0.4925	0.095*
H15C	0.0017	1.3260	0.4276	0.095*
C16	0.5855 (2)	0.7748 (2)	0.37574 (19)	0.0278 (5)
C17	0.4814 (3)	0.7679 (2)	0.4670 (2)	0.0336 (6)
H17	0.3937	0.8274	0.4800	0.040*
C18	0.5006 (3)	0.6761 (3)	0.5412 (2)	0.0374 (6)
H18	0.4269	0.6734	0.6036	0.045*
C19	0.6278 (3)	0.5892 (2)	0.5229 (2)	0.0368 (6)
C20	0.7350 (3)	0.5956 (3)	0.4324 (2)	0.0401 (7)
H20	0.8232	0.5369	0.4200	0.048*
C21	0.7138 (3)	0.6872 (2)	0.3603 (2)	0.0358 (6)
H21	0.7882	0.6908	0.2987	0.043*
O4	0.6572 (2)	0.49350 (18)	0.58887 (16)	0.0497 (5)
C22	0.5438 (4)	0.4776 (3)	0.6770 (2)	0.0535 (8)
H22A	0.5745	0.4014	0.7133	0.080*
H22B	0.4671	0.4737	0.6529	0.080*
H22C	0.5122	0.5466	0.7250	0.080*
C23	0.6975 (3)	1.1077 (2)	−0.00337 (19)	0.0288 (6)
C24	0.8097 (3)	1.1146 (2)	−0.0889 (2)	0.0331 (6)
H24	0.8837	1.0426	−0.1120	0.040*
C25	0.8182 (3)	1.2239 (3)	−0.1427 (2)	0.0388 (7)
H25	0.8970	1.2259	−0.2013	0.047*
C26	0.7116 (3)	1.3288 (3)	−0.1102 (3)	0.0462 (8)
C27	0.5945 (3)	1.3235 (3)	−0.0260 (3)	0.0552 (9)
H27	0.5188	1.3948	−0.0050	0.066*
C28	0.5887 (3)	1.2144 (3)	0.0267 (2)	0.0439 (7)
H28	0.5092	1.2120	0.0845	0.053*
O5	0.7101 (3)	1.4427 (2)	−0.1539 (2)	0.0649 (7)
C29	0.8299 (4)	1.4529 (3)	−0.2379 (3)	0.0724 (12)
H29A	0.8150	1.5374	−0.2636	0.109*
H29B	0.8458	1.3980	−0.2947	0.109*
H29C	0.9111	1.4304	−0.2129	0.109*
C30	0.7942 (2)	0.8771 (2)	0.00659 (18)	0.0263 (5)
C31	0.9055 (3)	0.8098 (2)	0.0393 (2)	0.0311 (6)
H31	0.9170	0.8354	0.0999	0.037*
C32	1.0011 (3)	0.7058 (2)	−0.0136 (2)	0.0346 (6)
H32	1.0753	0.6606	0.0117	0.042*
C33	0.9874 (3)	0.6688 (2)	−0.1030 (2)	0.0348 (6)
C34	0.8765 (3)	0.7350 (2)	−0.1371 (2)	0.0372 (6)
H34	0.8656	0.7094	−0.1979	0.045*
C35	0.7816 (3)	0.8378 (2)	−0.0837 (2)	0.0325 (6)
H35	0.7068	0.8822	−0.1087	0.039*
O6	1.0774 (2)	0.56990 (18)	−0.16166 (16)	0.0488 (5)
C36	1.1992 (3)	0.5104 (3)	−0.1328 (3)	0.0553 (9)
H36A	1.2514	0.5693	−0.1355	0.083*
H36B	1.2575	0.4433	−0.1815	0.083*
H36C	1.1724	0.4778	−0.0617	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0302 (10)	0.0386 (11)	0.0321 (10)	−0.0100 (9)	−0.0089 (8)	−0.0124 (8)
C1	0.0251 (12)	0.0290 (13)	0.0252 (13)	−0.0059 (10)	−0.0098 (10)	−0.0055 (10)
C2	0.0198 (11)	0.0292 (13)	0.0251 (12)	−0.0030 (10)	−0.0069 (10)	−0.0069 (10)
C3	0.0260 (12)	0.0352 (14)	0.0259 (13)	−0.0077 (11)	−0.0085 (10)	−0.0033 (11)
C4	0.0257 (13)	0.0454 (16)	0.0283 (14)	−0.0108 (12)	−0.0090 (11)	−0.0096 (12)
C5	0.0294 (13)	0.0461 (17)	0.0357 (15)	−0.0172 (12)	−0.0105 (11)	−0.0065 (12)
C6	0.0284 (13)	0.0458 (16)	0.0299 (14)	−0.0157 (12)	−0.0078 (11)	−0.0036 (12)
C7	0.0206 (11)	0.0335 (14)	0.0252 (13)	−0.0057 (10)	−0.0069 (10)	−0.0064 (11)
C8	0.0232 (12)	0.0324 (14)	0.0265 (13)	−0.0099 (10)	−0.0077 (10)	−0.0033 (11)
O2	0.0245 (9)	0.0464 (12)	0.0350 (11)	−0.0128 (9)	−0.0093 (8)	−0.0077 (9)
C9	0.0241 (12)	0.0304 (13)	0.0219 (12)	−0.0074 (10)	−0.0083 (10)	0.0011 (10)
C10	0.0276 (13)	0.0326 (14)	0.0318 (14)	−0.0083 (11)	−0.0108 (11)	−0.0024 (11)
C11	0.0326 (14)	0.0310 (14)	0.0345 (15)	−0.0043 (11)	−0.0114 (11)	−0.0057 (11)
C12	0.0238 (12)	0.0358 (15)	0.0313 (14)	−0.0028 (11)	−0.0089 (11)	−0.0008 (11)
C13	0.0252 (13)	0.0385 (16)	0.0432 (16)	−0.0097 (12)	−0.0124 (11)	−0.0052 (12)
C14	0.0313 (13)	0.0296 (14)	0.0401 (15)	−0.0089 (11)	−0.0149 (11)	−0.0070 (12)
O3	0.0249 (9)	0.0459 (12)	0.0577 (13)	0.0011 (9)	−0.0124 (9)	−0.0146 (10)
C15	0.0373 (17)	0.048 (2)	0.088 (3)	0.0054 (15)	−0.0054 (17)	−0.0256 (19)
C16	0.0282 (12)	0.0269 (13)	0.0314 (14)	−0.0086 (10)	−0.0121 (11)	−0.0023 (11)
C17	0.0295 (13)	0.0334 (15)	0.0343 (15)	−0.0040 (11)	−0.0085 (11)	−0.0028 (12)
C18	0.0382 (15)	0.0398 (16)	0.0322 (15)	−0.0105 (13)	−0.0095 (12)	0.0024 (12)
C19	0.0424 (16)	0.0311 (15)	0.0409 (16)	−0.0085 (12)	−0.0208 (13)	0.0041 (12)
C20	0.0318 (14)	0.0375 (16)	0.0482 (17)	−0.0012 (12)	−0.0167 (13)	0.0014 (13)
C21	0.0290 (13)	0.0382 (15)	0.0376 (15)	−0.0053 (12)	−0.0104 (12)	−0.0011 (12)
O4	0.0573 (13)	0.0429 (12)	0.0485 (12)	−0.0092 (10)	−0.0235 (11)	0.0130 (10)
C22	0.069 (2)	0.053 (2)	0.0463 (19)	−0.0244 (17)	−0.0260 (17)	0.0173 (15)
C23	0.0298 (13)	0.0308 (14)	0.0304 (13)	−0.0102 (11)	−0.0131 (11)	−0.0030 (11)
C24	0.0346 (14)	0.0370 (15)	0.0331 (14)	−0.0121 (12)	−0.0156 (12)	−0.0005 (12)
C25	0.0472 (16)	0.0461 (17)	0.0353 (15)	−0.0235 (14)	−0.0209 (13)	0.0047 (13)
C26	0.063 (2)	0.0354 (16)	0.058 (2)	−0.0203 (15)	−0.0383 (17)	0.0077 (14)
C27	0.0498 (19)	0.0309 (16)	0.085 (3)	−0.0034 (14)	−0.0262 (18)	−0.0073 (16)
C28	0.0381 (16)	0.0384 (16)	0.0529 (19)	−0.0082 (13)	−0.0121 (14)	−0.0041 (14)
O5	0.0901 (18)	0.0392 (13)	0.0827 (18)	−0.0270 (13)	−0.0457 (15)	0.0141 (12)
C29	0.104 (3)	0.063 (2)	0.079 (3)	−0.053 (2)	−0.049 (3)	0.030 (2)
C30	0.0270 (12)	0.0284 (13)	0.0254 (13)	−0.0119 (10)	−0.0066 (10)	−0.0011 (10)
C31	0.0327 (13)	0.0365 (15)	0.0269 (13)	−0.0120 (12)	−0.0099 (11)	−0.0033 (11)
C32	0.0317 (13)	0.0367 (15)	0.0355 (15)	−0.0070 (12)	−0.0123 (12)	−0.0016 (12)
C33	0.0363 (14)	0.0297 (14)	0.0379 (15)	−0.0124 (12)	−0.0063 (12)	−0.0051 (12)
C34	0.0460 (16)	0.0373 (16)	0.0336 (15)	−0.0139 (13)	−0.0146 (13)	−0.0092 (12)
C35	0.0361 (14)	0.0368 (15)	0.0303 (14)	−0.0137 (12)	−0.0146 (11)	−0.0009 (11)
O6	0.0504 (12)	0.0380 (12)	0.0553 (13)	−0.0011 (10)	−0.0171 (10)	−0.0201 (10)
C36	0.0436 (18)	0.0416 (18)	0.070 (2)	0.0033 (14)	−0.0113 (16)	−0.0210 (16)

Geometric parameters (Å, º)

O1—H1A	0.82 (3)	C18—H18	0.950
O1—H1B	0.81 (3)	C18—C19	1.382 (4)
O1—C1	1.448 (3)	C19—C20	1.386 (4)
C1—C2	1.543 (3)	C19—O4	1.371 (3)
C1—C9	1.537 (3)	C20—H20	0.950
C1—C16	1.535 (3)	C20—C21	1.380 (4)
C2—C3	1.401 (3)	C21—H21	0.950
C2—C7	1.410 (3)	O4—C22	1.433 (4)
C3—H3	0.950	C22—H22A	0.980
C3—C4	1.379 (3)	C22—H22B	0.980
C4—H4	0.950	C22—H22C	0.980
C4—C5	1.375 (4)	C23—C24	1.379 (4)
C5—H5	0.950	C23—C28	1.396 (4)
C5—C6	1.387 (4)	C24—H24	0.950
C6—H6	0.950	C24—C25	1.395 (4)
C6—C7	1.401 (3)	C25—H25	0.950
C7—C8	1.555 (3)	C25—C26	1.376 (4)
C8—O2	1.442 (3)	C26—C27	1.397 (5)
C8—C23	1.527 (3)	C26—O5	1.376 (3)
C8—C30	1.536 (3)	C27—H27	0.950
O2—H2A	0.81 (3)	C27—C28	1.382 (4)
O2—H2B	0.81 (3)	C28—H28	0.950
C9—C10	1.384 (3)	O5—C29	1.427 (4)
C9—C14	1.390 (3)	C29—H29A	0.980
C10—H10	0.950	C29—H29B	0.980
C10—C11	1.393 (3)	C29—H29C	0.980
C11—H11	0.950	C30—C31	1.384 (3)
C11—C12	1.375 (4)	C30—C35	1.398 (3)
C12—C13	1.385 (4)	C31—H31	0.950
C12—O3	1.373 (3)	C31—C32	1.393 (4)
C13—H13	0.950	C32—H32	0.950
C13—C14	1.383 (3)	C32—C33	1.381 (4)
C14—H14	0.950	C33—C34	1.387 (4)
O3—C15	1.414 (4)	C33—O6	1.367 (3)
C15—H15A	0.980	C34—H34	0.950
C15—H15B	0.980	C34—C35	1.384 (4)
C15—H15C	0.980	C35—H35	0.950
C16—C17	1.376 (3)	O6—C36	1.428 (4)
C16—C21	1.397 (3)	C36—H36A	0.980
C17—H17	0.950	C36—H36B	0.980
C17—C18	1.397 (4)	C36—H36C	0.980
H1A—O1—H1B	100 (6)	C17—C18—C19	119.3 (3)
H1A—O1—C1	106 (4)	H18—C18—C19	120.3
H1B—O1—C1	108 (5)	C18—C19—C20	119.7 (2)
O1—C1—C2	112.68 (19)	C18—C19—O4	124.3 (3)
O1—C1—C9	108.26 (19)	C20—C19—O4	116.0 (2)
O1—C1—C16	103.18 (19)	C19—C20—H20	120.0
C2—C1—C9	109.42 (19)	C19—C20—C21	120.0 (3)
C2—C1—C16	111.75 (19)	H20—C20—C21	120.0
C9—C1—C16	111.41 (19)	C16—C21—C20	121.5 (3)
C1—C2—C3	115.0 (2)	C16—C21—H21	119.2
C1—C2—C7	126.8 (2)	C20—C21—H21	119.2
C3—C2—C7	118.0 (2)	C19—O4—C22	116.8 (2)
C2—C3—H3	118.4	O4—C22—H22A	109.5
C2—C3—C4	123.1 (2)	O4—C22—H22B	109.5
H3—C3—C4	118.4	O4—C22—H22C	109.5
C3—C4—H4	120.5	H22A—C22—H22B	109.5
C3—C4—C5	119.0 (2)	H22A—C22—H22C	109.5
H4—C4—C5	120.5	H22B—C22—H22C	109.5
C4—C5—H5	120.4	C8—C23—C24	123.9 (2)
C4—C5—C6	119.2 (2)	C8—C23—C28	118.5 (2)
H5—C5—C6	120.4	C24—C23—C28	117.5 (3)
C5—C6—H6	118.6	C23—C24—H24	118.9
C5—C6—C7	122.9 (2)	C23—C24—C25	122.1 (3)
H6—C6—C7	118.6	H24—C24—C25	118.9
C2—C7—C6	117.7 (2)	C24—C25—H25	120.3
C2—C7—C8	126.8 (2)	C24—C25—C26	119.5 (3)
C6—C7—C8	115.3 (2)	H25—C25—C26	120.3
C7—C8—O2	109.78 (19)	C25—C26—C27	119.6 (3)
C7—C8—C23	110.1 (2)	C25—C26—O5	125.0 (3)
C7—C8—C30	109.83 (19)	C27—C26—O5	115.5 (3)
O2—C8—C23	105.20 (19)	C26—C27—H27	120.0
O2—C8—C30	109.71 (19)	C26—C27—C28	120.0 (3)
C23—C8—C30	112.1 (2)	H27—C27—C28	120.0
C8—O2—H2A	108 (4)	C23—C28—C27	121.3 (3)
C8—O2—H2B	111 (6)	C23—C28—H28	119.4
H2A—O2—H2B	103 (7)	C27—C28—H28	119.4
C1—C9—C10	122.2 (2)	C26—O5—C29	117.3 (3)
C1—C9—C14	120.0 (2)	O5—C29—H29A	109.5
C10—C9—C14	117.7 (2)	O5—C29—H29B	109.5
C9—C10—H10	119.1	O5—C29—H29C	109.5
C9—C10—C11	121.8 (2)	H29A—C29—H29B	109.5
H10—C10—C11	119.1	H29A—C29—H29C	109.5
C10—C11—H11	120.2	H29B—C29—H29C	109.5
C10—C11—C12	119.6 (2)	C8—C30—C31	122.5 (2)
H11—C11—C12	120.2	C8—C30—C35	120.1 (2)
C11—C12—C13	119.6 (2)	C31—C30—C35	117.3 (2)
C11—C12—O3	125.0 (2)	C30—C31—H31	118.9
C13—C12—O3	115.4 (2)	C30—C31—C32	122.2 (2)
C12—C13—H13	119.8	H31—C31—C32	118.9
C12—C13—C14	120.4 (2)	C31—C32—H32	120.2
H13—C13—C14	119.8	C31—C32—C33	119.6 (2)
C9—C14—C13	121.0 (2)	H32—C32—C33	120.2
C9—C14—H14	119.5	C32—C33—C34	119.1 (3)
C13—C14—H14	119.5	C32—C33—O6	124.1 (3)
C12—O3—C15	117.5 (2)	C34—C33—O6	116.9 (2)
O3—C15—H15A	109.5	C33—C34—H34	119.5
O3—C15—H15B	109.5	C33—C34—C35	120.9 (2)
O3—C15—H15C	109.5	H34—C34—C35	119.5
H15A—C15—H15B	109.5	C30—C35—C34	120.9 (2)
H15A—C15—H15C	109.5	C30—C35—H35	119.6
H15B—C15—H15C	109.5	C34—C35—H35	119.6
C1—C16—C17	123.5 (2)	C33—O6—C36	116.5 (2)
C1—C16—C21	119.0 (2)	O6—C36—H36A	109.5
C17—C16—C21	117.4 (2)	O6—C36—H36B	109.5
C16—C17—H17	119.0	O6—C36—H36C	109.5
C16—C17—C18	122.1 (2)	H36A—C36—H36B	109.5
H17—C17—C18	119.0	H36A—C36—H36C	109.5
C17—C18—H18	120.3	H36B—C36—H36C	109.5
O1—C1—C2—C3	−145.1 (2)	C21—C16—C17—C18	−1.2 (4)
O1—C1—C2—C7	39.6 (3)	C16—C17—C18—C19	0.0 (4)
C9—C1—C2—C3	94.4 (2)	C17—C18—C19—C20	1.2 (4)
C9—C1—C2—C7	−80.9 (3)	C17—C18—C19—O4	−178.4 (3)
C16—C1—C2—C3	−29.5 (3)	C18—C19—C20—C21	−1.1 (4)
C16—C1—C2—C7	155.2 (2)	O4—C19—C20—C21	178.5 (3)
C1—C2—C3—C4	−177.5 (2)	C19—C20—C21—C16	−0.2 (4)
C7—C2—C3—C4	−1.8 (4)	C1—C16—C21—C20	−175.2 (2)
C2—C3—C4—C5	1.5 (4)	C17—C16—C21—C20	1.3 (4)
C3—C4—C5—C6	−0.7 (4)	C18—C19—O4—C22	6.1 (4)
C4—C5—C6—C7	0.4 (4)	C20—C19—O4—C22	−173.4 (3)
C5—C6—C7—C2	−0.7 (4)	C7—C8—C23—C24	103.8 (3)
C5—C6—C7—C8	−175.4 (2)	C7—C8—C23—C28	−72.4 (3)
C1—C2—C7—C6	176.5 (2)	O2—C8—C23—C24	−138.0 (2)
C1—C2—C7—C8	−9.5 (4)	O2—C8—C23—C28	45.8 (3)
C3—C2—C7—C6	1.3 (3)	C30—C8—C23—C24	−18.8 (3)
C3—C2—C7—C8	175.4 (2)	C30—C8—C23—C28	165.0 (2)
C2—C7—C8—O2	39.8 (3)	C8—C23—C24—C25	−174.4 (2)
C2—C7—C8—C23	155.2 (2)	C28—C23—C24—C25	1.8 (4)
C2—C7—C8—C30	−80.9 (3)	C23—C24—C25—C26	−0.2 (4)
C6—C7—C8—O2	−146.0 (2)	C24—C25—C26—C27	−2.1 (4)
C6—C7—C8—C23	−30.7 (3)	C24—C25—C26—O5	177.3 (3)
C6—C7—C8—C30	93.3 (3)	C25—C26—C27—C28	2.6 (5)
O1—C1—C9—C10	−150.8 (2)	O5—C26—C27—C28	−176.8 (3)
O1—C1—C9—C14	33.6 (3)	C26—C27—C28—C23	−0.9 (5)
C2—C1—C9—C10	−27.7 (3)	C8—C23—C28—C27	175.2 (3)
C2—C1—C9—C14	156.8 (2)	C24—C23—C28—C27	−1.3 (4)
C16—C1—C9—C10	96.4 (3)	C25—C26—O5—C29	−1.5 (4)
C16—C1—C9—C14	−79.1 (3)	C27—C26—O5—C29	177.9 (3)
C1—C9—C10—C11	−174.9 (2)	C7—C8—C30—C31	−9.3 (3)
C14—C9—C10—C11	0.7 (4)	C7—C8—C30—C35	172.6 (2)
C9—C10—C11—C12	0.4 (4)	O2—C8—C30—C31	−130.0 (2)
C10—C11—C12—C13	−1.2 (4)	O2—C8—C30—C35	51.9 (3)
C10—C11—C12—O3	178.7 (2)	C23—C8—C30—C31	113.4 (3)
C11—C12—C13—C14	1.0 (4)	C23—C8—C30—C35	−64.7 (3)
O3—C12—C13—C14	−179.0 (2)	C8—C30—C31—C32	−179.1 (2)
C12—C13—C14—C9	0.2 (4)	C35—C30—C31—C32	−0.9 (4)
C1—C9—C14—C13	174.8 (2)	C30—C31—C32—C33	1.3 (4)
C10—C9—C14—C13	−1.0 (4)	C31—C32—C33—C34	−1.3 (4)
C11—C12—O3—C15	−5.9 (4)	C31—C32—C33—O6	178.4 (2)
C13—C12—O3—C15	174.0 (3)	C32—C33—C34—C35	0.9 (4)
O1—C1—C16—C17	−115.2 (3)	O6—C33—C34—C35	−178.8 (2)
O1—C1—C16—C21	61.1 (3)	C33—C34—C35—C30	−0.5 (4)
C2—C1—C16—C17	123.5 (3)	C8—C30—C35—C34	178.7 (2)
C2—C1—C16—C21	−60.2 (3)	C31—C30—C35—C34	0.5 (4)
C9—C1—C16—C17	0.7 (3)	C32—C33—O6—C36	−6.4 (4)
C9—C1—C16—C21	177.1 (2)	C34—C33—O6—C36	173.3 (3)
C1—C16—C17—C18	175.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O2	0.81 (3)	1.88 (5)	2.601 (3)	148 (7)
O2—H2A···O1	0.81 (3)	1.87 (4)	2.601 (3)	149 (6)
O2—H2B···O2^i	0.81 (3)	1.94 (3)	2.745 (4)	168 (8)

Symmetry code: (i) −x+1, −y+2, −z.