1-(2-Fur­yl)-3-hydr­oxy-3-(4-phenyl­phen­yl)prop-2-en-1-one

In the title compound, C₁₉H₁₄O₃, two independent mol­ecules exist in the enol form with normal values for bond lengths and angles. The crystal packing is stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.058
• wR factor = 0.158
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

1-(2-Furyl)-3-hydroxy-3-(4-phenylphenyl)prop-2-en-1-one

Crystal data

C19H14O3	Z = 4
Mr = 290.30	F(000) = 608
Triclinic, P1	Dx = 1.313 Mg m^−3
Hall symbol: -P 1	Melting point: 318 K
a = 9.9489 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4042 (11) Å	Cell parameters from 3694 reflections
c = 16.1706 (17) Å	θ = 2.3–27.7°
α = 90.113 (2)°	µ = 0.09 mm^−1
β = 100.547 (3)°	T = 297 K
γ = 116.292 (3)°	Plate, yellow
V = 1468.7 (3) Å^3	0.30 × 0.10 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer	5972 independent reflections
Radiation source: fine-focus sealed tube	4868 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 0 pixels mm^-1	θmax = 26.5°, θmin = 2.3°
φ and ω scans	h = −12→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→13
Tmin = 0.983, Tmax = 0.994	l = −14→20
9454 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0798P)^2 + 0.2029P] where P = (Fo^2 + 2Fc^2)/3
5972 reflections	(Δ/σ)max < 0.001
403 parameters	Δρmax = 0.17 e Å^−3
2 restraints	Δρmin = −0.30 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃, 400 MHz): 6.60–6.61(m, 1H, furyl-H), 6.82(s, 1H, enol CH), 7.26–7.28(m, 2H, Ar—H), 7.41–7.50(m, 3H, Ar—H), 7.63–7.66(m, 2H, Ar—H), 7.71(d, 2H, J =8.0 Hz, Ar—H), 8.04(d, 2H, J =8.0 Hz, Ar—H), 16.32(br s, 1H, enol OH); IR (KBr, ν cm^-1): 1604 (C ═O), 1517 (C ═ C); calculated for C₁₉H₁₄O₃: C 78.61, H 4.86%; found: C 78.57, H 4.88%.

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.

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

	x	y	z	Uiso*/Ueq
C1	0.3929 (2)	0.8063 (2)	−0.03002 (13)	0.0520 (5)
H1	0.4669	0.7920	0.0074	0.062*
C2	0.4225 (2)	0.8563 (2)	−0.10648 (14)	0.0614 (5)
H2	0.5154	0.8743	−0.1205	0.074*
C3	0.3156 (2)	0.8799 (2)	−0.16252 (13)	0.0566 (5)
H3	0.3359	0.9142	−0.2142	0.068*
C4	0.1787 (2)	0.8523 (2)	−0.14120 (12)	0.0562 (5)
H4	0.1060	0.8684	−0.1787	0.067*
C5	0.1478 (2)	0.8011 (2)	−0.06485 (11)	0.0481 (4)
H5	0.0541	0.7825	−0.0516	0.058*
C6	0.25465 (18)	0.77676 (17)	−0.00733 (11)	0.0405 (4)
C7	0.22091 (19)	0.71803 (17)	0.07418 (11)	0.0400 (4)
C8	0.07056 (19)	0.6307 (2)	0.08275 (11)	0.0461 (4)
H8	−0.0097	0.6136	0.0375	0.055*
C9	0.0385 (2)	0.5695 (2)	0.15644 (11)	0.0469 (4)
H9	−0.0628	0.5113	0.1599	0.056*
C10	0.15506 (19)	0.59325 (18)	0.22589 (11)	0.0423 (4)
C11	0.3053 (2)	0.6827 (2)	0.21854 (11)	0.0476 (4)
H11	0.3853	0.7013	0.2642	0.057*
C12	0.3368 (2)	0.7438 (2)	0.14472 (12)	0.0473 (4)
H12	0.4379	0.8038	0.1417	0.057*
C13	0.1231 (2)	0.52574 (19)	0.30468 (11)	0.0450 (4)
C14	−0.0197 (2)	0.4557 (2)	0.32226 (12)	0.0486 (4)
H14	−0.1037	0.4512	0.2836	0.058*
C15	−0.0423 (2)	0.3895 (2)	0.39858 (12)	0.0484 (4)
C16	−0.1983 (2)	0.3117 (2)	0.41233 (11)	0.0495 (4)
C17	−0.3370 (2)	0.2820 (2)	0.36566 (13)	0.0601 (5)
H17	−0.3570	0.3098	0.3120	0.072*
C18	−0.4465 (3)	0.2006 (3)	0.41333 (15)	0.0727 (6)
H18	−0.5523	0.1635	0.3974	0.087*
C19	−0.3668 (3)	0.1878 (3)	0.48573 (15)	0.0753 (7)
H19	−0.4105	0.1394	0.5295	0.090*
C20	0.1384 (2)	0.1539 (2)	0.31490 (11)	0.0496 (4)
H20	0.1451	0.2453	0.3087	0.060*
C21	0.0986 (2)	0.0883 (2)	0.38649 (12)	0.0577 (5)
H21	0.0785	0.1357	0.4278	0.069*
C22	0.0884 (3)	−0.0459 (2)	0.39741 (12)	0.0608 (5)
H22	0.0618	−0.0897	0.4460	0.073*
C23	0.1177 (3)	−0.1152 (2)	0.33596 (13)	0.0634 (6)
H23	0.1103	−0.2066	0.3428	0.076*
C24	0.1581 (2)	−0.0497 (2)	0.26381 (12)	0.0541 (5)
H24	0.1785	−0.0975	0.2228	0.065*
C25	0.16859 (18)	0.08609 (19)	0.25186 (10)	0.0407 (4)
C26	0.20649 (18)	0.15531 (18)	0.17357 (10)	0.0385 (4)
C27	0.2739 (2)	0.3045 (2)	0.17195 (11)	0.0481 (4)
H27	0.3005	0.3627	0.2218	0.058*
C28	0.3020 (2)	0.36777 (19)	0.09802 (11)	0.0471 (4)
H28	0.3454	0.4675	0.0987	0.057*
C29	0.26640 (17)	0.28461 (18)	0.02271 (10)	0.0391 (4)
C30	0.2015 (2)	0.13567 (19)	0.02409 (11)	0.0440 (4)
H30	0.1781	0.0779	−0.0255	0.053*
C31	0.1716 (2)	0.07266 (19)	0.09746 (10)	0.0438 (4)
H31	0.1270	−0.0272	0.0964	0.053*
C32	0.29240 (18)	0.35407 (19)	−0.05611 (11)	0.0416 (4)
C33	0.2836 (2)	0.2852 (2)	−0.13130 (11)	0.0467 (4)
H33	0.2616	0.1884	−0.1342	0.056*
C34	0.30756 (19)	0.3605 (2)	−0.20382 (11)	0.0482 (4)
C35	0.3099 (2)	0.2919 (2)	−0.28171 (11)	0.0532 (5)
C36	0.3363 (3)	0.3415 (3)	−0.35672 (13)	0.0730 (7)
H36	0.3542	0.4327	−0.3725	0.088*
C37	0.3317 (3)	0.2285 (4)	−0.40648 (15)	0.0856 (8)
H37	0.3463	0.2307	−0.4617	0.103*
C38	0.3029 (3)	0.1187 (3)	−0.36054 (15)	0.0801 (7)
H38	0.2936	0.0299	−0.3790	0.096*
O1	0.24502 (16)	0.53698 (17)	0.35901 (9)	0.0629 (4)
H1A	0.207 (3)	0.492 (3)	0.4002 (12)	0.094*
O2	0.06794 (16)	0.39441 (16)	0.45385 (9)	0.0618 (4)
O3	−0.21468 (17)	0.25387 (16)	0.48781 (9)	0.0652 (4)
O4	0.32615 (16)	0.49128 (14)	−0.05001 (8)	0.0548 (3)
H4A	0.337 (3)	0.516 (3)	−0.1007 (9)	0.082*
O5	0.33190 (16)	0.49142 (16)	−0.20409 (8)	0.0606 (4)
O6	0.28868 (17)	0.15240 (17)	−0.28267 (9)	0.0661 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0461 (10)	0.0573 (12)	0.0588 (12)	0.0283 (9)	0.0123 (8)	0.0115 (9)
C2	0.0562 (12)	0.0715 (14)	0.0671 (13)	0.0329 (11)	0.0267 (10)	0.0180 (11)
C3	0.0662 (13)	0.0578 (12)	0.0484 (11)	0.0285 (10)	0.0166 (9)	0.0083 (9)
C4	0.0601 (12)	0.0636 (13)	0.0473 (11)	0.0327 (10)	0.0041 (9)	0.0048 (9)
C5	0.0431 (9)	0.0524 (11)	0.0504 (10)	0.0239 (8)	0.0072 (8)	0.0006 (8)
C6	0.0406 (9)	0.0320 (8)	0.0474 (9)	0.0155 (7)	0.0084 (7)	−0.0007 (7)
C7	0.0420 (9)	0.0338 (8)	0.0458 (9)	0.0190 (7)	0.0080 (7)	−0.0011 (7)
C8	0.0398 (9)	0.0515 (10)	0.0439 (10)	0.0200 (8)	0.0030 (7)	−0.0017 (8)
C9	0.0390 (9)	0.0485 (10)	0.0482 (10)	0.0152 (8)	0.0094 (7)	0.0005 (8)
C10	0.0462 (9)	0.0387 (9)	0.0449 (9)	0.0221 (8)	0.0081 (7)	0.0001 (7)
C11	0.0405 (9)	0.0509 (10)	0.0478 (10)	0.0204 (8)	0.0012 (7)	0.0021 (8)
C12	0.0362 (9)	0.0472 (10)	0.0542 (11)	0.0156 (8)	0.0077 (8)	0.0057 (8)
C13	0.0506 (10)	0.0416 (9)	0.0439 (10)	0.0240 (8)	0.0038 (8)	−0.0006 (7)
C14	0.0498 (10)	0.0491 (10)	0.0468 (10)	0.0231 (8)	0.0075 (8)	0.0088 (8)
C15	0.0591 (11)	0.0427 (10)	0.0457 (10)	0.0262 (9)	0.0077 (8)	0.0031 (8)
C16	0.0638 (11)	0.0434 (10)	0.0419 (10)	0.0240 (9)	0.0131 (8)	0.0096 (8)
C17	0.0633 (12)	0.0674 (13)	0.0470 (11)	0.0276 (10)	0.0096 (9)	0.0100 (9)
C18	0.0602 (13)	0.0815 (16)	0.0647 (14)	0.0207 (12)	0.0152 (11)	0.0111 (12)
C19	0.0711 (15)	0.0760 (16)	0.0646 (15)	0.0164 (12)	0.0255 (12)	0.0216 (12)
C20	0.0601 (11)	0.0555 (11)	0.0411 (9)	0.0347 (9)	0.0060 (8)	0.0019 (8)
C21	0.0702 (13)	0.0779 (14)	0.0393 (10)	0.0442 (11)	0.0161 (9)	0.0062 (9)
C22	0.0713 (13)	0.0749 (15)	0.0418 (11)	0.0363 (11)	0.0157 (9)	0.0172 (10)
C23	0.0862 (15)	0.0570 (12)	0.0513 (12)	0.0363 (11)	0.0138 (10)	0.0121 (9)
C24	0.0750 (13)	0.0546 (11)	0.0422 (10)	0.0377 (10)	0.0119 (9)	0.0041 (8)
C25	0.0408 (9)	0.0479 (10)	0.0346 (8)	0.0229 (8)	0.0027 (7)	0.0007 (7)
C26	0.0359 (8)	0.0449 (9)	0.0372 (9)	0.0220 (7)	0.0038 (6)	0.0008 (7)
C27	0.0561 (10)	0.0441 (10)	0.0380 (9)	0.0192 (8)	0.0049 (8)	−0.0055 (7)
C28	0.0520 (10)	0.0365 (9)	0.0475 (10)	0.0158 (8)	0.0092 (8)	0.0000 (7)
C29	0.0336 (8)	0.0457 (9)	0.0394 (9)	0.0197 (7)	0.0060 (6)	0.0033 (7)
C30	0.0513 (10)	0.0430 (9)	0.0373 (9)	0.0213 (8)	0.0079 (7)	−0.0029 (7)
C31	0.0504 (10)	0.0376 (9)	0.0417 (9)	0.0187 (8)	0.0085 (7)	0.0006 (7)
C32	0.0349 (8)	0.0436 (9)	0.0461 (10)	0.0185 (7)	0.0058 (7)	0.0056 (7)
C33	0.0486 (10)	0.0519 (10)	0.0410 (9)	0.0242 (8)	0.0086 (7)	0.0061 (8)
C34	0.0362 (9)	0.0608 (12)	0.0439 (10)	0.0201 (8)	0.0040 (7)	0.0075 (8)
C35	0.0441 (10)	0.0710 (13)	0.0417 (10)	0.0252 (9)	0.0040 (8)	0.0078 (9)
C36	0.0769 (15)	0.0976 (19)	0.0470 (12)	0.0401 (14)	0.0165 (11)	0.0185 (12)
C37	0.0785 (16)	0.135 (3)	0.0398 (12)	0.0448 (17)	0.0133 (11)	−0.0022 (14)
C38	0.0813 (16)	0.099 (2)	0.0545 (14)	0.0381 (15)	0.0096 (12)	−0.0180 (13)
O1	0.0525 (8)	0.0792 (10)	0.0540 (9)	0.0294 (7)	0.0052 (6)	0.0134 (7)
O2	0.0649 (9)	0.0705 (9)	0.0527 (8)	0.0351 (7)	0.0062 (7)	0.0147 (7)
O3	0.0687 (9)	0.0684 (9)	0.0517 (8)	0.0246 (8)	0.0131 (7)	0.0225 (7)
O4	0.0681 (9)	0.0460 (8)	0.0513 (8)	0.0256 (6)	0.0153 (7)	0.0100 (6)
O5	0.0682 (9)	0.0621 (9)	0.0538 (8)	0.0310 (7)	0.0133 (7)	0.0175 (7)
O6	0.0721 (9)	0.0735 (10)	0.0504 (8)	0.0318 (8)	0.0097 (7)	−0.0023 (7)

Geometric parameters (Å, º)

C1—C2	1.373 (3)	C20—C25	1.387 (2)
C1—C6	1.390 (2)	C20—H20	0.9300
C1—H1	0.9300	C21—C22	1.369 (3)
C2—C3	1.375 (3)	C21—H21	0.9300
C2—H2	0.9300	C22—C23	1.371 (3)
C3—C4	1.372 (3)	C22—H22	0.9300
C3—H3	0.9300	C23—C24	1.385 (3)
C4—C5	1.378 (3)	C23—H23	0.9300
C4—H4	0.9300	C24—C25	1.387 (3)
C5—C6	1.392 (2)	C24—H24	0.9300
C5—H5	0.9300	C25—C26	1.484 (2)
C6—C7	1.486 (2)	C26—C27	1.394 (2)
C7—C12	1.395 (2)	C26—C31	1.396 (2)
C7—C8	1.398 (2)	C27—C28	1.380 (2)
C8—C9	1.375 (2)	C27—H27	0.9300
C8—H8	0.9300	C28—C29	1.387 (2)
C9—C10	1.391 (2)	C28—H28	0.9300
C9—H9	0.9300	C29—C30	1.392 (2)
C10—C11	1.396 (2)	C29—C32	1.474 (2)
C10—C13	1.474 (2)	C30—C31	1.373 (2)
C11—C12	1.375 (2)	C30—H30	0.9300
C11—H11	0.9300	C31—H31	0.9300
C12—H12	0.9300	C32—O4	1.313 (2)
C13—O1	1.320 (2)	C32—C33	1.379 (2)
C13—C14	1.364 (3)	C33—C34	1.410 (2)
C14—C15	1.420 (3)	C33—H33	0.9300
C14—H14	0.9300	C34—O5	1.274 (2)
C15—O2	1.263 (2)	C34—C35	1.455 (3)
C15—C16	1.458 (3)	C35—C36	1.344 (3)
C16—C17	1.345 (3)	C35—O6	1.371 (3)
C16—O3	1.367 (2)	C36—C37	1.403 (4)
C17—C18	1.411 (3)	C36—H36	0.9300
C17—H17	0.9300	C37—C38	1.315 (4)
C18—C19	1.330 (3)	C37—H37	0.9300
C18—H18	0.9300	C38—O6	1.355 (3)
C19—O3	1.351 (3)	C38—H38	0.9300
C19—H19	0.9300	O1—H1A	0.86 (1)
C20—C21	1.376 (3)	O4—H4A	0.87 (1)
C2—C1—C6	121.38 (18)	C25—C20—H20	119.4
C2—C1—H1	119.3	C22—C21—C20	120.63 (18)
C6—C1—H1	119.3	C22—C21—H21	119.7
C1—C2—C3	120.48 (18)	C20—C21—H21	119.7
C1—C2—H2	119.8	C21—C22—C23	119.29 (18)
C3—C2—H2	119.8	C21—C22—H22	120.4
C4—C3—C2	119.13 (18)	C23—C22—H22	120.4
C4—C3—H3	120.4	C22—C23—C24	120.4 (2)
C2—C3—H3	120.4	C22—C23—H23	119.8
C3—C4—C5	120.71 (18)	C24—C23—H23	119.8
C3—C4—H4	119.6	C23—C24—C25	120.87 (18)
C5—C4—H4	119.6	C23—C24—H24	119.6
C4—C5—C6	120.93 (17)	C25—C24—H24	119.6
C4—C5—H5	119.5	C24—C25—C20	117.62 (17)
C6—C5—H5	119.5	C24—C25—C26	121.44 (15)
C1—C6—C5	117.37 (17)	C20—C25—C26	120.92 (16)
C1—C6—C7	121.25 (16)	C27—C26—C31	117.14 (15)
C5—C6—C7	121.36 (15)	C27—C26—C25	121.85 (15)
C12—C7—C8	116.94 (16)	C31—C26—C25	120.98 (15)
C12—C7—C6	121.97 (15)	C28—C27—C26	121.48 (16)
C8—C7—C6	121.07 (15)	C28—C27—H27	119.3
C9—C8—C7	121.61 (16)	C26—C27—H27	119.3
C9—C8—H8	119.2	C27—C28—C29	120.88 (16)
C7—C8—H8	119.2	C27—C28—H28	119.6
C8—C9—C10	121.04 (16)	C29—C28—H28	119.6
C8—C9—H9	119.5	C28—C29—C30	117.98 (15)
C10—C9—H9	119.5	C28—C29—C32	120.01 (16)
C9—C10—C11	117.76 (16)	C30—C29—C32	121.98 (15)
C9—C10—C13	121.78 (16)	C31—C30—C29	121.11 (16)
C11—C10—C13	120.46 (16)	C31—C30—H30	119.4
C12—C11—C10	120.97 (16)	C29—C30—H30	119.4
C12—C11—H11	119.5	C30—C31—C26	121.39 (16)
C10—C11—H11	119.5	C30—C31—H31	119.3
C11—C12—C7	121.64 (16)	C26—C31—H31	119.3
C11—C12—H12	119.2	O4—C32—C33	120.94 (16)
C7—C12—H12	119.2	O4—C32—C29	114.39 (15)
O1—C13—C14	121.00 (17)	C33—C32—C29	124.67 (16)
O1—C13—C10	114.75 (16)	C32—C33—C34	120.42 (18)
C14—C13—C10	124.25 (16)	C32—C33—H33	119.8
C13—C14—C15	121.10 (17)	C34—C33—H33	119.8
C13—C14—H14	119.4	O5—C34—C33	122.23 (17)
C15—C14—H14	119.4	O5—C34—C35	116.91 (17)
O2—C15—C14	122.04 (18)	C33—C34—C35	120.84 (18)
O2—C15—C16	119.46 (17)	C36—C35—O6	109.6 (2)
C14—C15—C16	118.50 (17)	C36—C35—C34	132.0 (2)
C17—C16—O3	109.52 (17)	O6—C35—C34	118.32 (17)
C17—C16—C15	133.80 (18)	C35—C36—C37	106.4 (2)
O3—C16—C15	116.68 (16)	C35—C36—H36	126.8
C16—C17—C18	107.16 (19)	C37—C36—H36	126.8
C16—C17—H17	126.4	C38—C37—C36	107.3 (2)
C18—C17—H17	126.4	C38—C37—H37	126.3
C19—C18—C17	105.7 (2)	C36—C37—H37	126.3
C19—C18—H18	127.1	C37—C38—O6	110.9 (2)
C17—C18—H18	127.1	C37—C38—H38	124.5
C18—C19—O3	111.70 (19)	O6—C38—H38	124.5
C18—C19—H19	124.2	C13—O1—H1A	103.1 (19)
O3—C19—H19	124.2	C19—O3—C16	105.89 (16)
C21—C20—C25	121.16 (19)	C32—O4—H4A	103.5 (17)
C21—C20—H20	119.4	C38—O6—C35	105.78 (19)
C6—C1—C2—C3	0.7 (3)	C22—C23—C24—C25	−0.5 (3)
C1—C2—C3—C4	−0.3 (3)	C23—C24—C25—C20	0.5 (3)
C2—C3—C4—C5	−0.2 (3)	C23—C24—C25—C26	−177.84 (18)
C3—C4—C5—C6	0.3 (3)	C21—C20—C25—C24	−0.4 (3)
C2—C1—C6—C5	−0.6 (3)	C21—C20—C25—C26	178.00 (17)
C2—C1—C6—C7	177.90 (18)	C24—C25—C26—C27	−154.95 (17)
C4—C5—C6—C1	0.1 (3)	C20—C25—C26—C27	26.8 (2)
C4—C5—C6—C7	−178.42 (16)	C24—C25—C26—C31	27.0 (2)
C1—C6—C7—C12	27.1 (2)	C20—C25—C26—C31	−151.31 (17)
C5—C6—C7—C12	−154.46 (17)	C31—C26—C27—C28	1.3 (3)
C1—C6—C7—C8	−151.16 (18)	C25—C26—C27—C28	−176.81 (16)
C5—C6—C7—C8	27.3 (2)	C26—C27—C28—C29	−1.2 (3)
C12—C7—C8—C9	−1.9 (3)	C27—C28—C29—C30	0.0 (3)
C6—C7—C8—C9	176.50 (16)	C27—C28—C29—C32	177.89 (16)
C7—C8—C9—C10	0.5 (3)	C28—C29—C30—C31	0.9 (3)
C8—C9—C10—C11	0.8 (3)	C32—C29—C30—C31	−176.89 (15)
C8—C9—C10—C13	−178.51 (16)	C29—C30—C31—C26	−0.8 (3)
C9—C10—C11—C12	−0.8 (3)	C27—C26—C31—C30	−0.4 (3)
C13—C10—C11—C12	178.59 (16)	C25—C26—C31—C30	177.79 (15)
C10—C11—C12—C7	−0.6 (3)	C28—C29—C32—O4	−10.3 (2)
C8—C7—C12—C11	1.9 (3)	C30—C29—C32—O4	167.46 (15)
C6—C7—C12—C11	−176.42 (16)	C28—C29—C32—C33	169.57 (16)
C9—C10—C13—O1	168.43 (16)	C30—C29—C32—C33	−12.7 (3)
C11—C10—C13—O1	−10.9 (2)	O4—C32—C33—C34	−1.4 (3)
C9—C10—C13—C14	−11.3 (3)	C29—C32—C33—C34	178.78 (15)
C11—C10—C13—C14	169.39 (17)	C32—C33—C34—O5	−2.8 (3)
O1—C13—C14—C15	−1.6 (3)	C32—C33—C34—C35	175.37 (16)
C10—C13—C14—C15	178.12 (16)	O5—C34—C35—C36	1.5 (3)
C13—C14—C15—O2	1.2 (3)	C33—C34—C35—C36	−176.8 (2)
C13—C14—C15—C16	−177.81 (17)	O5—C34—C35—O6	178.04 (15)
O2—C15—C16—C17	−176.7 (2)	C33—C34—C35—O6	−0.3 (3)
C14—C15—C16—C17	2.3 (3)	O6—C35—C36—C37	−0.1 (2)
O2—C15—C16—O3	3.2 (3)	C34—C35—C36—C37	176.7 (2)
C14—C15—C16—O3	−177.79 (16)	C35—C36—C37—C38	0.2 (3)
O3—C16—C17—C18	−0.5 (2)	C36—C37—C38—O6	−0.3 (3)
C15—C16—C17—C18	179.4 (2)	C18—C19—O3—C16	0.2 (3)
C16—C17—C18—C19	0.6 (3)	C17—C16—O3—C19	0.2 (2)
C17—C18—C19—O3	−0.5 (3)	C15—C16—O3—C19	−179.73 (18)
C25—C20—C21—C22	0.2 (3)	C37—C38—O6—C35	0.2 (3)
C20—C21—C22—C23	−0.3 (3)	C36—C35—O6—C38	−0.1 (2)
C21—C22—C23—C24	0.4 (3)	C34—C35—O6—C38	−177.37 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O5	0.87 (1)	1.68 (2)	2.5026 (19)	157 (3)
O1—H1A···O2	0.86 (1)	1.70 (2)	2.518 (2)	157 (3)