Crystal structure of 4-[(2E)-3-(4-meth-oxy-phen-yl)prop-2-eno-yl]phenyl benzoate.

In the title compound, C23H18O4, the meth-oxy-benzene ring and attached C=C grouping are disordered over two sets of sites in a 0.823 (5):0.177 (5) ratio. The dihedral angles between the central benzene ring and the pendant phenyl and meth-oxy-benzene ring (major orientation) are 51.21 (1) and 51.6 (1)°, respectively. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R 2 (2)(28) loops.

Related literature

For background to flavenoids, see: Di Carlo et al. (1999 ▶); Rackova et al. (2005 ▶); Harborne & Williams (2000 ▶). For related structures, see: Moreno-Fuquen et al. (2014 ▶); Jasinski et al. (2011 ▶); Sathya et al. (2014 ▶).

Experimental

Crystal data

C23H18O4

M = 358.37

Monoclinic,

a = 20.146 (5) Å

b = 14.513 (5) Å

c = 6.187 (5) Å

β = 94.828 (5)°

V = 1802.5 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.969, T max = 0.978

17041 measured reflections

3170 independent reflections

2523 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.195

S = 1.11

3170 reflections

320 parameters

334 restraints

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814018303/hb7255sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018303/hb7255Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814018303/hb7255Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814018303/hb7255fig1.tif

The mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814018303/hb7255fig2.tif

The packing of the mol­ecules in the crystal structure. The dashed lines indicate the hydrogen bonds.

Click here for additional data file.

. DOI: 10.1107/S1600536814018303/hb7255fig3.tif

Experimental procedure.

CCDC reference: 1018848

Additional supporting information: crystallographic information; 3D view; checkCIF report

C23H18O4	F(000) = 752
Mr = 358.37	Dx = 1.321 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3462 reflections
a = 20.146 (5) Å	θ = 2.6–25.6°
b = 14.513 (5) Å	µ = 0.09 mm−1
c = 6.187 (5) Å	T = 293 K
β = 94.828 (5)°	Block, yellow
V = 1802.5 (16) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker APEXII CCD diffractometer	3170 independent reflections
Radiation source: fine-focus sealed tube	2523 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
ω and φ scan	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −23→23
Tmin = 0.969, Tmax = 0.978	k = −17→17
17041 measured reflections	l = −7→7

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056	H-atom parameters constrained
wR(F2) = 0.195	w = 1/[σ2(Fo2) + (0.0812P)2 + 1.0118P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
3170 reflections	Δρmax = 0.21 e Å−3
320 parameters	Δρmin = −0.17 e Å−3
334 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0043 (17)

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)
C1	0.89122 (16)	0.6485 (2)	0.0011 (5)	0.0631 (8)
H1	0.8506	0.6659	−0.0694	0.076*
C2	0.94911 (18)	0.6612 (2)	−0.0966 (5)	0.0746 (9)
H2	0.9474	0.6882	−0.2332	0.090*
C3	1.00923 (18)	0.6348 (2)	0.0027 (6)	0.0789 (10)
H3	1.0480	0.6438	−0.0660	0.095*
C4	1.01200 (17)	0.5948 (3)	0.2058 (6)	0.0773 (9)
H4	1.0527	0.5760	0.2737	0.093*
C5	0.95459 (15)	0.5829 (2)	0.3071 (5)	0.0665 (8)
H5	0.9566	0.5568	0.4448	0.080*
C6	0.89386 (13)	0.60929 (18)	0.2065 (4)	0.0514 (7)
C7	0.83392 (14)	0.59524 (18)	0.3243 (5)	0.0540 (7)
C8	0.71707 (13)	0.62650 (18)	0.3021 (4)	0.0515 (7)
C9	0.70646 (14)	0.66395 (18)	0.5013 (5)	0.0555 (7)
H9	0.7417	0.6891	0.5888	0.067*
C10	0.64306 (14)	0.66356 (18)	0.5684 (5)	0.0555 (7)
H10	0.6356	0.6871	0.7040	0.067*
C11	0.59009 (14)	0.62820 (18)	0.4352 (5)	0.0575 (7)
C12	0.60283 (15)	0.5913 (2)	0.2357 (5)	0.0687 (9)
H12	0.5679	0.5673	0.1449	0.082*
C13	0.66607 (15)	0.5899 (2)	0.1713 (5)	0.0625 (8)
H13	0.6742	0.5641	0.0385	0.075*
O1	0.83266 (11)	0.55704 (16)	0.4953 (3)	0.0757 (7)
O2	0.77922 (9)	0.63206 (14)	0.2161 (3)	0.0613 (6)
C14	0.5205 (2)	0.6314 (5)	0.4965 (9)	0.0649 (15)	0.823 (5)
C15	0.4662 (2)	0.6328 (4)	0.3246 (11)	0.0682 (15)	0.823 (5)
H15	0.4749	0.6488	0.1842	0.082*	0.823 (5)
C16	0.40600 (19)	0.6119 (2)	0.3661 (7)	0.0610 (10)	0.823 (5)
H16	0.3996	0.5946	0.5076	0.073*	0.823 (5)
O4	0.16821 (8)	0.61934 (12)	−0.1635 (3)	0.0731 (16)	0.823 (5)
C20	0.22860 (8)	0.61731 (12)	−0.0591 (3)	0.0506 (9)	0.823 (5)
C21	0.23058 (8)	0.57341 (12)	0.1410 (3)	0.0521 (10)	0.823 (5)
H21	0.1925	0.5454	0.1853	0.063*	0.823 (5)
C22	0.28953 (8)	0.57131 (12)	0.2749 (3)	0.0545 (10)	0.823 (5)
H22	0.2909	0.5419	0.4088	0.065*	0.823 (5)
C17	0.34650 (8)	0.61310 (12)	0.2087 (3)	0.0517 (11)	0.823 (5)
C18	0.34452 (8)	0.65700 (12)	0.0085 (3)	0.0569 (10)	0.823 (5)
H18	0.3826	0.6850	−0.0358	0.068*	0.823 (5)
C19	0.28557 (8)	0.65910 (12)	−0.1254 (3)	0.0567 (11)	0.823 (5)
H19	0.2842	0.6885	−0.2593	0.068*	0.823 (5)
O3	0.5124 (2)	0.6334 (5)	0.6900 (8)	0.0909 (14)	0.823 (5)
C23	0.1593 (5)	0.6736 (9)	−0.3550 (11)	0.073 (2)	0.823 (5)
H23A	0.1704	0.7365	−0.3209	0.109*	0.823 (5)
H23B	0.1137	0.6699	−0.4135	0.109*	0.823 (5)
H23C	0.1878	0.6509	−0.4599	0.109*	0.823 (5)
C14'	0.5326 (7)	0.624 (3)	0.575 (3)	0.063 (6)	0.177 (5)
C15'	0.4574 (6)	0.6085 (10)	0.476 (2)	0.038 (3)	0.177 (5)
H15'	0.4262	0.5844	0.5633	0.046*	0.177 (5)
C16'	0.4385 (10)	0.6305 (14)	0.263 (3)	0.042 (3)	0.177 (5)
H16'	0.4730	0.6518	0.1852	0.050*	0.177 (5)
O4'	0.1697 (4)	0.6196 (6)	−0.1703 (13)	0.060 (6)	0.177 (5)
C20'	0.2427 (4)	0.6185 (6)	−0.0378 (13)	0.062 (4)	0.177 (5)
C21'	0.2604 (4)	0.5803 (6)	0.1649 (13)	0.050 (4)	0.177 (5)
H21'	0.2283	0.5520	0.2417	0.060*	0.177 (5)
C22'	0.3262 (4)	0.5842 (6)	0.2528 (13)	0.045 (4)	0.177 (5)
H22'	0.3380	0.5586	0.3884	0.054*	0.177 (5)
C17'	0.3742 (4)	0.6264 (6)	0.1381 (13)	0.044 (3)	0.177 (5)
C18'	0.3565 (4)	0.6646 (6)	−0.0646 (13)	0.069 (4)	0.177 (5)
H18'	0.3887	0.6929	−0.1413	0.083*	0.177 (5)
C19'	0.2908 (4)	0.6607 (6)	−0.1525 (13)	0.063 (4)	0.177 (5)
H19'	0.2790	0.6863	−0.2881	0.076*	0.177 (5)
O3'	0.5304 (9)	0.628 (2)	0.774 (2)	0.076 (5)	0.177 (5)
C23'	0.161 (3)	0.661 (5)	−0.380 (6)	0.095 (14)	0.177 (5)
H23D	0.1932	0.7093	−0.3896	0.142*	0.177 (5)
H23E	0.1171	0.6853	−0.4042	0.142*	0.177 (5)
H23F	0.1680	0.6149	−0.4884	0.142*	0.177 (5)

	U11	U22	U33	U12	U13	U23
C1	0.072 (2)	0.0635 (19)	0.0548 (17)	0.0032 (14)	0.0081 (14)	0.0041 (14)
C2	0.089 (3)	0.073 (2)	0.0646 (19)	−0.0015 (17)	0.0248 (18)	0.0038 (16)
C3	0.073 (2)	0.080 (2)	0.088 (2)	−0.0085 (18)	0.0321 (19)	−0.0092 (19)
C4	0.061 (2)	0.088 (2)	0.083 (2)	0.0019 (17)	0.0072 (17)	−0.0069 (19)
C5	0.0627 (19)	0.070 (2)	0.0667 (19)	0.0064 (15)	0.0046 (15)	0.0015 (16)
C6	0.0607 (17)	0.0449 (15)	0.0492 (15)	−0.0006 (12)	0.0076 (12)	−0.0016 (11)
C7	0.0587 (17)	0.0467 (15)	0.0565 (16)	0.0035 (12)	0.0039 (13)	0.0043 (13)
C8	0.0540 (16)	0.0437 (14)	0.0567 (16)	0.0053 (11)	0.0032 (12)	0.0052 (12)
C9	0.0545 (17)	0.0505 (15)	0.0603 (17)	−0.0017 (12)	−0.0031 (13)	−0.0034 (13)
C10	0.0613 (18)	0.0482 (15)	0.0569 (16)	0.0027 (12)	0.0036 (13)	−0.0027 (13)
C11	0.0544 (17)	0.0446 (15)	0.0727 (19)	0.0032 (12)	0.0010 (14)	−0.0049 (13)
C12	0.0598 (19)	0.0595 (18)	0.083 (2)	0.0052 (14)	−0.0134 (16)	−0.0228 (16)
C13	0.067 (2)	0.0611 (18)	0.0575 (17)	0.0132 (14)	−0.0039 (14)	−0.0113 (14)
O1	0.0743 (14)	0.0904 (16)	0.0639 (13)	0.0121 (11)	0.0139 (10)	0.0304 (12)
O2	0.0593 (12)	0.0684 (13)	0.0569 (12)	0.0094 (9)	0.0094 (9)	0.0141 (10)
C14	0.057 (3)	0.059 (3)	0.077 (3)	0.004 (3)	0.001 (3)	−0.009 (3)
C15	0.056 (3)	0.064 (3)	0.087 (4)	0.001 (3)	0.018 (3)	−0.001 (3)
C16	0.065 (2)	0.0484 (19)	0.071 (2)	0.0033 (16)	0.015 (2)	−0.0013 (17)
O4	0.074 (3)	0.082 (3)	0.065 (3)	−0.010 (3)	0.013 (3)	0.005 (3)
C20	0.056 (2)	0.0449 (19)	0.0518 (19)	0.0005 (15)	0.0107 (16)	−0.0033 (16)
C21	0.060 (2)	0.0455 (19)	0.053 (2)	−0.0032 (16)	0.0162 (17)	−0.0025 (15)
C22	0.063 (3)	0.0454 (19)	0.056 (2)	0.0036 (18)	0.013 (2)	0.0043 (16)
C17	0.065 (3)	0.040 (2)	0.051 (2)	0.0039 (19)	0.013 (2)	0.0008 (17)
C18	0.060 (2)	0.048 (2)	0.063 (3)	−0.0060 (16)	0.0084 (18)	0.0041 (18)
C19	0.068 (3)	0.051 (2)	0.053 (2)	−0.001 (2)	0.015 (2)	0.0058 (19)
O3	0.058 (3)	0.125 (3)	0.091 (3)	0.003 (3)	0.013 (2)	−0.003 (3)
C23	0.062 (3)	0.101 (5)	0.056 (4)	−0.007 (3)	0.005 (3)	−0.004 (3)
C14'	0.034 (8)	0.062 (9)	0.086 (12)	0.019 (8)	−0.030 (9)	−0.010 (11)
C15'	0.023 (6)	0.050 (6)	0.044 (6)	−0.002 (5)	0.012 (5)	0.006 (5)
C16'	0.040 (7)	0.041 (6)	0.049 (8)	−0.002 (7)	0.035 (6)	0.006 (6)
O4'	0.054 (10)	0.061 (10)	0.066 (10)	−0.015 (9)	0.018 (9)	0.003 (10)
C20'	0.066 (7)	0.056 (7)	0.064 (7)	−0.012 (6)	−0.001 (6)	−0.012 (7)
C21'	0.047 (8)	0.050 (7)	0.055 (7)	−0.003 (6)	0.020 (6)	−0.003 (6)
C22'	0.053 (8)	0.054 (8)	0.031 (6)	0.007 (7)	0.025 (7)	0.017 (6)
C17'	0.056 (6)	0.039 (6)	0.041 (6)	−0.009 (5)	0.035 (5)	0.007 (5)
C18'	0.095 (9)	0.063 (8)	0.051 (8)	0.007 (7)	0.007 (7)	0.000 (7)
C19'	0.068 (8)	0.054 (8)	0.067 (8)	−0.008 (8)	−0.002 (7)	−0.001 (7)
O3'	0.045 (9)	0.111 (11)	0.070 (11)	0.009 (8)	−0.016 (7)	−0.006 (11)
C23'	0.15 (3)	0.079 (19)	0.051 (17)	0.015 (19)	−0.010 (18)	0.029 (18)

C1—C2	1.371 (4)	C20—C21	1.3900
C1—C6	1.389 (4)	C20—C19	1.3900
C1—H1	0.9300	C21—C22	1.3900
C2—C3	1.366 (5)	C21—H21	0.9300
C2—H2	0.9300	C22—C17	1.3900
C3—C4	1.381 (5)	C22—H22	0.9300
C3—H3	0.9300	C17—C18	1.3900
C4—C5	1.372 (4)	C18—C19	1.3900
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.379 (4)	C19—H19	0.9300
C5—H5	0.9300	C23—H23A	0.9600
C6—C7	1.476 (4)	C23—H23B	0.9600
C7—O1	1.196 (3)	C23—H23C	0.9600
C7—O2	1.351 (3)	C14'—O3'	1.234 (11)
C8—C13	1.361 (4)	C14'—C15'	1.60 (2)
C8—C9	1.379 (4)	C15'—C16'	1.38 (3)
C8—O2	1.403 (3)	C15'—H15'	0.9300
C9—C10	1.376 (4)	C16'—C17'	1.45 (2)
C9—H9	0.9300	C16'—H16'	0.9300
C10—C11	1.391 (4)	O4'—C23'	1.426 (9)
C10—H10	0.9300	O4'—C20'	1.6236
C11—C12	1.389 (4)	C20'—C21'	1.3900
C11—C14	1.484 (5)	C20'—C19'	1.3900
C11—C14'	1.505 (10)	C21'—C22'	1.3900
C12—C13	1.367 (4)	C21'—H21'	0.9300
C12—H12	0.9300	C22'—C17'	1.3900
C13—H13	0.9300	C22'—H22'	0.9300
C14—O3	1.222 (6)	C17'—C18'	1.3900
C14—C15	1.460 (7)	C18'—C19'	1.3900
C15—C16	1.297 (6)	C18'—H18'	0.9300
C15—H15	0.9300	C19'—H19'	0.9300
C16—C17	1.480 (4)	C23'—H23D	0.9600
C16—H16	0.9300	C23'—H23E	0.9600
O4—C20	1.3287	C23'—H23F	0.9600
O4—C23	1.421 (5)
C2—C1—C6	119.3 (3)	O4—C20—C21	113.5
C2—C1—H1	120.3	O4—C20—C19	126.3
C6—C1—H1	120.3	C21—C20—C19	120.0
C3—C2—C1	121.3 (3)	C22—C21—C20	120.0
C3—C2—H2	119.4	C22—C21—H21	120.0
C1—C2—H2	119.4	C20—C21—H21	120.0
C2—C3—C4	119.6 (3)	C21—C22—C17	120.0
C2—C3—H3	120.2	C21—C22—H22	120.0
C4—C3—H3	120.2	C17—C22—H22	120.0
C5—C4—C3	119.8 (3)	C22—C17—C18	120.0
C5—C4—H4	120.1	C22—C17—C16	116.38 (18)
C3—C4—H4	120.1	C18—C17—C16	123.54 (18)
C4—C5—C6	120.6 (3)	C17—C18—C19	120.0
C4—C5—H5	119.7	C17—C18—H18	120.0
C6—C5—H5	119.7	C19—C18—H18	120.0
C5—C6—C1	119.4 (3)	C18—C19—C20	120.0
C5—C6—C7	118.0 (3)	C18—C19—H19	120.0
C1—C6—C7	122.6 (3)	C20—C19—H19	120.0
O1—C7—O2	123.0 (3)	O3'—C14'—C11	131.7 (18)
O1—C7—C6	125.4 (3)	O3'—C14'—C15'	106.0 (12)
O2—C7—C6	111.6 (2)	C11—C14'—C15'	122.3 (13)
C13—C8—C9	121.3 (3)	C16'—C15'—C14'	120.6 (15)
C13—C8—O2	116.7 (3)	C16'—C15'—H15'	119.7
C9—C8—O2	121.7 (2)	C14'—C15'—H15'	119.7
C10—C9—C8	119.1 (3)	C15'—C16'—C17'	131.3 (16)
C10—C9—H9	120.5	C15'—C16'—H16'	114.3
C8—C9—H9	120.5	C17'—C16'—H16'	114.3
C9—C10—C11	120.5 (3)	C23'—O4'—C20'	120 (2)
C9—C10—H10	119.7	C21'—C20'—C19'	120.0
C11—C10—H10	119.7	C21'—C20'—O4'	127.7
C12—C11—C10	118.6 (3)	C19'—C20'—O4'	112.3
C12—C11—C14	119.3 (3)	C20'—C21'—C22'	120.0
C10—C11—C14	122.1 (3)	C20'—C21'—H21'	120.0
C12—C11—C14'	134.9 (11)	C22'—C21'—H21'	120.0
C10—C11—C14'	105.2 (10)	C17'—C22'—C21'	120.0
C14—C11—C14'	20.7 (7)	C17'—C22'—H22'	120.0
C13—C12—C11	120.8 (3)	C21'—C22'—H22'	120.0
C13—C12—H12	119.6	C18'—C17'—C22'	120.0
C11—C12—H12	119.6	C18'—C17'—C16'	127.7 (8)
C8—C13—C12	119.7 (3)	C22'—C17'—C16'	112.1 (8)
C8—C13—H13	120.1	C17'—C18'—C19'	120.0
C12—C13—H13	120.1	C17'—C18'—H18'	120.0
C7—O2—C8	120.4 (2)	C19'—C18'—H18'	120.0
O3—C14—C15	124.1 (5)	C18'—C19'—C20'	120.0
O3—C14—C11	117.2 (4)	C18'—C19'—H19'	120.0
C15—C14—C11	118.7 (5)	C20'—C19'—H19'	120.0
C16—C15—C14	120.5 (6)	O4'—C23'—H23D	109.5
C16—C15—H15	119.7	O4'—C23'—H23E	109.5
C14—C15—H15	119.7	H23D—C23'—H23E	109.5
C15—C16—C17	125.9 (5)	O4'—C23'—H23F	109.5
C15—C16—H16	117.0	H23D—C23'—H23F	109.5
C17—C16—H16	117.0	H23E—C23'—H23F	109.5
C20—O4—C23	117.6 (4)
C6—C1—C2—C3	0.9 (5)	C23—O4—C20—C21	171.5 (7)
C1—C2—C3—C4	−0.2 (5)	C23—O4—C20—C19	−3.9 (7)
C2—C3—C4—C5	−0.8 (5)	O4—C20—C21—C22	−175.8
C3—C4—C5—C6	1.0 (5)	C19—C20—C21—C22	0.0
C4—C5—C6—C1	−0.2 (5)	C20—C21—C22—C17	0.0
C4—C5—C6—C7	−179.6 (3)	C21—C22—C17—C18	0.0
C2—C1—C6—C5	−0.8 (4)	C21—C22—C17—C16	176.82 (17)
C2—C1—C6—C7	178.6 (3)	C15—C16—C17—C22	167.8 (4)
C5—C6—C7—O1	−5.3 (4)	C15—C16—C17—C18	−15.6 (5)
C1—C6—C7—O1	175.3 (3)	C22—C17—C18—C19	0.0
C5—C6—C7—O2	174.1 (2)	C16—C17—C18—C19	−176.58 (18)
C1—C6—C7—O2	−5.3 (4)	C17—C18—C19—C20	0.0
C13—C8—C9—C10	0.4 (4)	O4—C20—C19—C18	175.2
O2—C8—C9—C10	174.3 (2)	C21—C20—C19—C18	0.0
C8—C9—C10—C11	−1.7 (4)	C12—C11—C14'—O3'	150 (3)
C9—C10—C11—C12	1.6 (4)	C10—C11—C14'—O3'	−16 (4)
C9—C10—C11—C14	−176.5 (4)	C14—C11—C14'—O3'	−163 (8)
C9—C10—C11—C14'	170.5 (15)	C12—C11—C14'—C15'	−27 (4)
C10—C11—C12—C13	−0.1 (5)	C10—C11—C14'—C15'	166 (2)
C14—C11—C12—C13	178.0 (4)	C14—C11—C14'—C15'	19 (2)
C14'—C11—C12—C13	−164.9 (18)	O3'—C14'—C15'—C16'	159 (2)
C9—C8—C13—C12	1.0 (4)	C11—C14'—C15'—C16'	−23 (4)
O2—C8—C13—C12	−173.1 (3)	C14'—C15'—C16'—C17'	−177 (2)
C11—C12—C13—C8	−1.2 (5)	C23'—O4'—C20'—C21'	−179 (3)
O1—C7—O2—C8	−0.2 (4)	C23'—O4'—C20'—C19'	0 (3)
C6—C7—O2—C8	−179.6 (2)	C19'—C20'—C21'—C22'	0.0
C13—C8—O2—C7	−126.4 (3)	O4'—C20'—C21'—C22'	178.8
C9—C8—O2—C7	59.5 (3)	C20'—C21'—C22'—C17'	0.0
C12—C11—C14—O3	155.5 (5)	C21'—C22'—C17'—C18'	0.0
C10—C11—C14—O3	−26.5 (8)	C21'—C22'—C17'—C16'	175.2 (10)
C14'—C11—C14—O3	12 (4)	C15'—C16'—C17'—C18'	167.7 (15)
C12—C11—C14—C15	−25.0 (7)	C15'—C16'—C17'—C22'	−7 (2)
C10—C11—C14—C15	153.0 (5)	C22'—C17'—C18'—C19'	0.0
C14'—C11—C14—C15	−169 (5)	C16'—C17'—C18'—C19'	−174.4 (11)
O3—C14—C15—C16	−18.4 (10)	C17'—C18'—C19'—C20'	0.0
C11—C14—C15—C16	162.1 (5)	C21'—C20'—C19'—C18'	0.0
C14—C15—C16—C17	178.2 (4)	O4'—C20'—C19'—C18'	−178.9

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O1i	0.93	2.56	3.280 (3)	135
C21′—H21′···O1i	0.93	2.65	3.546 (7)	163
C23′—H23F···O1ii	0.96	2.50	3.24 (7)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O1i	0.93	2.56	3.280 (3)	135
C21′—H21′⋯O1i	0.93	2.65	3.546 (7)	163
C23′—H23F⋯O1ii	0.96	2.50	3.24 (7)	135

Symmetry codes: (i) ; (ii) .