4-Cyano-3-fluoro-phenyl 4-(hexa-dec-yl-oxy)benzoate.

In the title compound, C30H40FNO3, the dihedral angle between the benzene rings is 57.76 (7)°. The alkyl chain adopts an all-trans conformation. In the crystal, mol-ecules are linked by pairs of C-H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For general background to the title compound and applications of fluorinated liquid crystals, see: Chigrinov et al. (2008 ▶); Reddy & Tschierske (2006 ▶); Hird & Toyne (1998 ▶); Roussel (1999 ▶). For a related structure, see: Al-Eryani et al. (2011 ▶).

Experimental

Crystal data

C30H40FNO3

M = 481.63

Monoclinic,

a = 22.937 (3) Å

b = 9.2022 (9) Å

c = 13.2859 (10) Å

β = 100.749 (8)°

V = 2755.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.596, T max = 0.985

10771 measured reflections

5379 independent reflections

2448 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.146

S = 0.96

5379 reflections

318 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.12 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814001871/is5333sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001871/is5333Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001871/is5333Isup3.cml

CCDC reference:

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

C30H40FNO3	F(000) = 1040
Mr = 481.63	Dx = 1.161 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2658 reflections
a = 22.937 (3) Å	θ = 3.9–28.9°
b = 9.2022 (9) Å	µ = 0.08 mm−1
c = 13.2859 (10) Å	T = 293 K
β = 100.749 (8)°	Block, white
V = 2755.1 (5) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	5379 independent reflections
Radiation source: fine-focus sealed tube	2448 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.6°
ω scans	h = −28→27
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −11→10
Tmin = 0.596, Tmax = 0.985	l = −15→16
10771 measured reflections

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)] = 0.059	H-atom parameters constrained
wR(F2) = 0.146	w = 1/[σ2(Fo2) + (0.0429P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max = 0.001
5379 reflections	Δρmax = 0.18 e Å−3
318 parameters	Δρmin = −0.12 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (4)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
F3	0.01653 (7)	0.95837 (17)	−0.72555 (9)	0.0945 (7)
O9	0.08886 (8)	0.82686 (18)	−0.37972 (10)	0.0720 (7)
O10	0.11933 (8)	0.59458 (19)	−0.37524 (11)	0.0774 (7)
O17	0.25399 (8)	0.84443 (17)	0.05228 (10)	0.0698 (6)
N8	−0.10909 (11)	0.7467 (3)	−0.81803 (16)	0.0974 (11)
C1	0.04873 (11)	0.8036 (3)	−0.47032 (16)	0.0588 (9)
C2	0.05447 (11)	0.8891 (3)	−0.55275 (16)	0.0643 (10)
C3	0.01283 (11)	0.8727 (3)	−0.64102 (16)	0.0621 (10)
C4	−0.03311 (11)	0.7750 (3)	−0.65010 (16)	0.0583 (9)
C5	−0.03811 (12)	0.6914 (3)	−0.56497 (17)	0.0714 (10)
C6	0.00309 (12)	0.7071 (3)	−0.47546 (17)	0.0712 (11)
C7	−0.07573 (12)	0.7596 (3)	−0.74352 (18)	0.0699 (10)
C10	0.12016 (11)	0.7104 (3)	−0.33365 (16)	0.0560 (9)
C11	0.15403 (10)	0.7469 (2)	−0.23164 (14)	0.0504 (8)
C12	0.18556 (11)	0.6385 (3)	−0.17480 (15)	0.0602 (9)
C13	0.21936 (11)	0.6657 (2)	−0.07876 (15)	0.0585 (9)
C14	0.22127 (11)	0.8039 (2)	−0.03907 (15)	0.0540 (8)
C15	0.18824 (11)	0.9125 (3)	−0.09427 (15)	0.0694 (10)
C16	0.15494 (11)	0.8840 (3)	−0.18988 (15)	0.0650 (10)
C18	0.28506 (11)	0.7371 (2)	0.11804 (14)	0.0562 (9)
C19	0.32012 (11)	0.8146 (2)	0.20936 (14)	0.0551 (8)
C20	0.35225 (10)	0.7152 (2)	0.29200 (14)	0.0546 (8)
C21	0.38807 (11)	0.7963 (2)	0.38133 (14)	0.0546 (9)
C22	0.42129 (11)	0.7045 (2)	0.46717 (14)	0.0541 (8)
C23	0.45679 (11)	0.7898 (2)	0.55487 (14)	0.0521 (8)
C24	0.49090 (10)	0.7010 (2)	0.64152 (13)	0.0531 (8)
C25	0.52575 (10)	0.7893 (2)	0.72853 (13)	0.0523 (8)
C26	0.56051 (10)	0.7018 (2)	0.81627 (14)	0.0540 (8)
C27	0.59459 (10)	0.7921 (2)	0.90214 (14)	0.0543 (8)
C28	0.62995 (11)	0.7061 (2)	0.99015 (14)	0.0548 (9)
C29	0.66382 (11)	0.7978 (2)	1.07614 (14)	0.0579 (9)
C30	0.69986 (11)	0.7133 (2)	1.16370 (14)	0.0600 (9)
C31	0.73187 (11)	0.8036 (2)	1.25108 (15)	0.0601 (9)
C32	0.76864 (11)	0.7210 (3)	1.33800 (15)	0.0662 (10)
C33	0.80091 (12)	0.8162 (3)	1.42314 (16)	0.0834 (11)
H2	0.08530	0.95560	−0.54900	0.0770*
H5	−0.06900	0.62510	−0.56830	0.0860*
H6	−0.00030	0.65150	−0.41840	0.0860*
H12	0.18420	0.54470	−0.20130	0.0720*
H13	0.24060	0.59100	−0.04150	0.0700*
H15	0.18840	1.00550	−0.06690	0.0830*
H16	0.13290	0.95810	−0.22650	0.0780*
H18A	0.31150	0.68300	0.08270	0.0670*
H18B	0.25730	0.66960	0.13970	0.0670*
H19A	0.29340	0.87620	0.23890	0.0660*
H19B	0.34900	0.87720	0.18620	0.0660*
H20A	0.32340	0.65430	0.31670	0.0660*
H20B	0.37850	0.65210	0.26260	0.0660*
H21A	0.41650	0.85740	0.35560	0.0660*
H21B	0.36150	0.86010	0.40950	0.0660*
H22A	0.44800	0.64060	0.43950	0.0650*
H22B	0.39300	0.64390	0.49370	0.0650*
H23A	0.48460	0.85110	0.52790	0.0620*
H23B	0.42990	0.85320	0.58240	0.0620*
H24A	0.51820	0.63810	0.61440	0.0640*
H24B	0.46320	0.63930	0.66870	0.0640*
H25A	0.49840	0.85200	0.75550	0.0630*
H25B	0.55320	0.85120	0.70110	0.0630*
H26A	0.53320	0.63960	0.84390	0.0650*
H26B	0.58820	0.63950	0.78960	0.0650*
H27A	0.56680	0.85400	0.92890	0.0650*
H27B	0.62160	0.85490	0.87430	0.0650*
H28A	0.60300	0.64310	1.01800	0.0660*
H28B	0.65790	0.64460	0.96360	0.0660*
H29A	0.69030	0.86180	1.04790	0.0690*
H29B	0.63570	0.85850	1.10310	0.0690*
H30A	0.67360	0.64670	1.19010	0.0720*
H30B	0.72890	0.65530	1.13700	0.0720*
H31A	0.75760	0.87120	1.22430	0.0720*
H31B	0.70270	0.86040	1.27820	0.0720*
H32A	0.79760	0.66300	1.31120	0.0790*
H32B	0.74300	0.65490	1.36630	0.0790*
H33A	0.82760	0.87960	1.39650	0.1250*
H33B	0.82300	0.75640	1.47610	0.1250*
H33C	0.77260	0.87330	1.45090	0.1250*

	U11	U22	U33	U12	U13	U23
F3	0.1042 (14)	0.1239 (13)	0.0487 (8)	−0.0370 (11)	−0.0027 (7)	0.0190 (8)
O9	0.0806 (14)	0.0730 (11)	0.0487 (9)	−0.0020 (10)	−0.0230 (8)	−0.0015 (8)
O10	0.0708 (14)	0.0826 (13)	0.0679 (11)	0.0087 (11)	−0.0152 (9)	−0.0231 (9)
O17	0.0810 (14)	0.0649 (10)	0.0495 (9)	0.0109 (10)	−0.0241 (8)	−0.0055 (8)
N8	0.088 (2)	0.113 (2)	0.0735 (15)	0.0049 (17)	−0.0308 (13)	−0.0068 (14)
C1	0.0608 (18)	0.0662 (16)	0.0429 (13)	0.0007 (14)	−0.0068 (11)	−0.0036 (12)
C2	0.0612 (18)	0.0727 (18)	0.0522 (14)	−0.0081 (14)	−0.0068 (12)	−0.0039 (12)
C3	0.0663 (19)	0.0713 (17)	0.0440 (14)	−0.0041 (15)	−0.0018 (12)	0.0036 (12)
C4	0.0539 (17)	0.0689 (17)	0.0449 (14)	0.0024 (14)	−0.0097 (11)	−0.0017 (12)
C5	0.0604 (19)	0.0788 (19)	0.0674 (16)	−0.0109 (15)	−0.0075 (13)	0.0036 (14)
C6	0.068 (2)	0.084 (2)	0.0562 (16)	−0.0095 (17)	−0.0024 (13)	0.0126 (13)
C7	0.066 (2)	0.0752 (18)	0.0602 (16)	0.0038 (15)	−0.0095 (13)	0.0005 (13)
C10	0.0503 (16)	0.0657 (16)	0.0479 (14)	0.0009 (14)	−0.0018 (11)	−0.0016 (12)
C11	0.0476 (15)	0.0592 (15)	0.0401 (12)	−0.0033 (13)	−0.0032 (10)	−0.0006 (10)
C12	0.0632 (18)	0.0571 (15)	0.0538 (14)	0.0046 (14)	−0.0057 (12)	−0.0109 (11)
C13	0.0615 (18)	0.0545 (14)	0.0517 (14)	0.0057 (13)	−0.0097 (12)	0.0009 (11)
C14	0.0558 (16)	0.0604 (15)	0.0393 (12)	0.0032 (13)	−0.0081 (11)	−0.0006 (11)
C15	0.089 (2)	0.0554 (15)	0.0524 (14)	0.0084 (15)	−0.0160 (13)	−0.0069 (11)
C16	0.0714 (19)	0.0585 (16)	0.0545 (14)	0.0032 (15)	−0.0157 (12)	0.0017 (12)
C18	0.0574 (17)	0.0617 (15)	0.0437 (13)	0.0033 (13)	−0.0056 (11)	−0.0002 (11)
C19	0.0553 (16)	0.0613 (15)	0.0433 (12)	0.0034 (13)	−0.0049 (11)	−0.0031 (10)
C20	0.0601 (17)	0.0562 (14)	0.0414 (12)	0.0014 (13)	−0.0062 (11)	0.0006 (10)
C21	0.0573 (17)	0.0591 (15)	0.0420 (12)	0.0000 (13)	−0.0050 (11)	0.0013 (10)
C22	0.0601 (17)	0.0524 (14)	0.0443 (12)	0.0026 (13)	−0.0045 (11)	−0.0014 (10)
C23	0.0569 (16)	0.0528 (14)	0.0407 (12)	−0.0010 (12)	−0.0058 (10)	0.0006 (10)
C24	0.0580 (17)	0.0526 (14)	0.0430 (12)	0.0034 (12)	−0.0054 (11)	−0.0027 (10)
C25	0.0555 (16)	0.0528 (14)	0.0434 (12)	−0.0029 (12)	−0.0043 (11)	0.0007 (10)
C26	0.0582 (17)	0.0554 (14)	0.0424 (12)	0.0039 (13)	−0.0058 (11)	−0.0010 (10)
C27	0.0595 (17)	0.0551 (14)	0.0417 (12)	−0.0017 (13)	−0.0076 (11)	0.0024 (10)
C28	0.0586 (17)	0.0583 (15)	0.0415 (12)	0.0015 (13)	−0.0062 (11)	0.0019 (10)
C29	0.0602 (17)	0.0612 (15)	0.0449 (13)	−0.0007 (13)	−0.0091 (11)	0.0027 (11)
C30	0.0672 (19)	0.0622 (16)	0.0426 (13)	0.0079 (14)	−0.0105 (11)	−0.0003 (11)
C31	0.0609 (18)	0.0679 (16)	0.0457 (13)	0.0006 (14)	−0.0054 (11)	−0.0012 (11)
C32	0.0667 (19)	0.0728 (17)	0.0504 (14)	0.0111 (15)	−0.0114 (12)	−0.0042 (12)
C33	0.084 (2)	0.098 (2)	0.0563 (15)	0.0051 (18)	−0.0173 (14)	−0.0121 (13)

F3—C3	1.388 (3)	C6—H6	0.9300
O9—C1	1.389 (3)	C12—H12	0.9300
O9—C10	1.369 (3)	C13—H13	0.9300
O10—C10	1.199 (3)	C15—H15	0.9300
O17—C14	1.355 (2)	C16—H16	0.9300
O17—C18	1.419 (2)	C18—H18A	0.9700
N8—C7	1.139 (3)	C18—H18B	0.9700
C1—C2	1.375 (3)	C19—H19A	0.9700
C1—C6	1.365 (4)	C19—H19B	0.9700
C2—C3	1.376 (3)	C20—H20A	0.9700
C3—C4	1.373 (4)	C20—H20B	0.9700
C4—C5	1.390 (3)	C21—H21A	0.9700
C4—C7	1.437 (3)	C21—H21B	0.9700
C5—C6	1.382 (3)	C22—H22A	0.9700
C10—C11	1.470 (3)	C22—H22B	0.9700
C11—C12	1.373 (3)	C23—H23A	0.9700
C11—C16	1.377 (3)	C23—H23B	0.9700
C12—C13	1.387 (3)	C24—H24A	0.9700
C13—C14	1.374 (3)	C24—H24B	0.9700
C14—C15	1.380 (3)	C25—H25A	0.9700
C15—C16	1.380 (3)	C25—H25B	0.9700
C18—C19	1.505 (3)	C26—H26A	0.9700
C19—C20	1.511 (3)	C26—H26B	0.9700
C20—C21	1.509 (3)	C27—H27A	0.9700
C21—C22	1.507 (3)	C27—H27B	0.9700
C22—C23	1.511 (3)	C28—H28A	0.9700
C23—C24	1.506 (3)	C28—H28B	0.9700
C24—C25	1.514 (3)	C29—H29A	0.9700
C25—C26	1.515 (3)	C29—H29B	0.9700
C26—C27	1.507 (3)	C30—H30A	0.9700
C27—C28	1.516 (3)	C30—H30B	0.9700
C28—C29	1.513 (3)	C31—H31A	0.9700
C29—C30	1.511 (3)	C31—H31B	0.9700
C30—C31	1.503 (3)	C32—H32A	0.9700
C31—C32	1.503 (3)	C32—H32B	0.9700
C32—C33	1.511 (3)	C33—H33A	0.9600
C2—H2	0.9300	C33—H33B	0.9600
C5—H5	0.9300	C33—H33C	0.9600
C1—O9—C10	118.32 (19)	C21—C20—H20A	109.00
C14—O17—C18	119.38 (16)	C21—C20—H20B	109.00
O9—C1—C2	117.1 (2)	H20A—C20—H20B	108.00
O9—C1—C6	121.5 (2)	C20—C21—H21A	108.00
C2—C1—C6	121.3 (2)	C20—C21—H21B	108.00
C1—C2—C3	117.5 (2)	C22—C21—H21A	108.00
F3—C3—C2	119.4 (2)	C22—C21—H21B	108.00
F3—C3—C4	117.56 (19)	H21A—C21—H21B	107.00
C2—C3—C4	123.1 (2)	C21—C22—H22A	109.00
C3—C4—C5	118.0 (2)	C21—C22—H22B	109.00
C3—C4—C7	121.9 (2)	C23—C22—H22A	109.00
C5—C4—C7	120.2 (2)	C23—C22—H22B	109.00
C4—C5—C6	119.7 (2)	H22A—C22—H22B	108.00
C1—C6—C5	120.4 (2)	C22—C23—H23A	108.00
N8—C7—C4	179.3 (3)	C22—C23—H23B	108.00
O9—C10—O10	121.9 (2)	C24—C23—H23A	108.00
O9—C10—C11	112.1 (2)	C24—C23—H23B	108.00
O10—C10—C11	126.0 (2)	H23A—C23—H23B	107.00
C10—C11—C12	118.35 (19)	C23—C24—H24A	109.00
C10—C11—C16	123.1 (2)	C23—C24—H24B	109.00
C12—C11—C16	118.51 (19)	C25—C24—H24A	109.00
C11—C12—C13	121.5 (2)	C25—C24—H24B	109.00
C12—C13—C14	119.5 (2)	H24A—C24—H24B	108.00
O17—C14—C13	124.83 (19)	C24—C25—H25A	108.00
O17—C14—C15	115.74 (18)	C24—C25—H25B	108.00
C13—C14—C15	119.4 (2)	C26—C25—H25A	108.00
C14—C15—C16	120.4 (2)	C26—C25—H25B	108.00
C11—C16—C15	120.6 (2)	H25A—C25—H25B	107.00
O17—C18—C19	107.34 (15)	C25—C26—H26A	109.00
C18—C19—C20	114.45 (16)	C25—C26—H26B	109.00
C19—C20—C21	113.10 (15)	C27—C26—H26A	109.00
C20—C21—C22	116.25 (16)	C27—C26—H26B	109.00
C21—C22—C23	114.59 (16)	H26A—C26—H26B	108.00
C22—C23—C24	115.84 (16)	C26—C27—H27A	109.00
C23—C24—C25	114.68 (15)	C26—C27—H27B	109.00
C24—C25—C26	115.43 (15)	C28—C27—H27A	109.00
C25—C26—C27	114.43 (15)	C28—C27—H27B	109.00
C26—C27—C28	115.06 (16)	H27A—C27—H27B	107.00
C27—C28—C29	114.63 (15)	C27—C28—H28A	109.00
C28—C29—C30	115.12 (16)	C27—C28—H28B	109.00
C29—C30—C31	115.37 (16)	C29—C28—H28A	109.00
C30—C31—C32	115.92 (17)	C29—C28—H28B	109.00
C31—C32—C33	114.1 (2)	H28A—C28—H28B	108.00
C1—C2—H2	121.00	C28—C29—H29A	108.00
C3—C2—H2	121.00	C28—C29—H29B	108.00
C4—C5—H5	120.00	C30—C29—H29A	109.00
C6—C5—H5	120.00	C30—C29—H29B	109.00
C1—C6—H6	120.00	H29A—C29—H29B	107.00
C5—C6—H6	120.00	C29—C30—H30A	108.00
C11—C12—H12	119.00	C29—C30—H30B	108.00
C13—C12—H12	119.00	C31—C30—H30A	108.00
C12—C13—H13	120.00	C31—C30—H30B	108.00
C14—C13—H13	120.00	H30A—C30—H30B	107.00
C14—C15—H15	120.00	C30—C31—H31A	108.00
C16—C15—H15	120.00	C30—C31—H31B	108.00
C11—C16—H16	120.00	C32—C31—H31A	108.00
C15—C16—H16	120.00	C32—C31—H31B	108.00
O17—C18—H18A	110.00	H31A—C31—H31B	107.00
O17—C18—H18B	110.00	C31—C32—H32A	109.00
C19—C18—H18A	110.00	C31—C32—H32B	109.00
C19—C18—H18B	110.00	C33—C32—H32A	109.00
H18A—C18—H18B	109.00	C33—C32—H32B	109.00
C18—C19—H19A	109.00	H32A—C32—H32B	108.00
C18—C19—H19B	109.00	C32—C33—H33A	109.00
C20—C19—H19A	109.00	C32—C33—H33B	110.00
C20—C19—H19B	109.00	C32—C33—H33C	109.00
H19A—C19—H19B	108.00	H33A—C33—H33B	109.00
C19—C20—H20A	109.00	H33A—C33—H33C	109.00
C19—C20—H20B	109.00	H33B—C33—H33C	110.00
C10—O9—C1—C2	−126.7 (3)	C10—C11—C12—C13	178.8 (2)
C10—O9—C1—C6	57.7 (3)	C16—C11—C12—C13	−2.1 (4)
C1—O9—C10—O10	9.4 (3)	C10—C11—C16—C15	−179.1 (2)
C1—O9—C10—C11	−171.6 (2)	C12—C11—C16—C15	1.9 (4)
C18—O17—C14—C13	−5.9 (3)	C11—C12—C13—C14	0.3 (4)
C18—O17—C14—C15	174.4 (2)	C12—C13—C14—O17	−178.0 (2)
C14—O17—C18—C19	176.4 (2)	C12—C13—C14—C15	1.7 (4)
O9—C1—C2—C3	−176.3 (2)	O17—C14—C15—C16	177.8 (2)
C6—C1—C2—C3	−0.7 (4)	C13—C14—C15—C16	−2.0 (4)
O9—C1—C6—C5	176.6 (2)	C14—C15—C16—C11	0.1 (4)
C2—C1—C6—C5	1.1 (4)	O17—C18—C19—C20	175.26 (19)
C1—C2—C3—F3	179.1 (2)	C18—C19—C20—C21	178.7 (2)
C1—C2—C3—C4	−0.6 (4)	C19—C20—C21—C22	179.8 (2)
F3—C3—C4—C5	−178.3 (2)	C20—C21—C22—C23	179.8 (2)
F3—C3—C4—C7	0.7 (4)	C21—C22—C23—C24	−179.5 (2)
C2—C3—C4—C5	1.4 (4)	C22—C23—C24—C25	−179.67 (19)
C2—C3—C4—C7	−179.6 (3)	C23—C24—C25—C26	−179.82 (19)
C3—C4—C5—C6	−0.9 (4)	C24—C25—C26—C27	−179.73 (19)
C7—C4—C5—C6	−180.0 (2)	C25—C26—C27—C28	−179.58 (19)
C4—C5—C6—C1	−0.3 (4)	C26—C27—C28—C29	−179.8 (2)
O9—C10—C11—C12	177.3 (2)	C27—C28—C29—C30	−179.3 (2)
O9—C10—C11—C16	−1.7 (3)	C28—C29—C30—C31	−177.9 (2)
O10—C10—C11—C12	−3.7 (4)	C29—C30—C31—C32	−179.1 (2)
O10—C10—C11—C16	177.3 (2)	C30—C31—C32—C33	178.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O10i	0.93	2.38	3.237 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O10i	0.93	2.38	3.237 (3)	153

Symmetry code: (i) .