4-[4-(Hept-yloxy)benzo-yloxy]phenyl 2-oxo-7-tri-fluoro-methyl-2H-chromene-3-carboxyl-ate.

The title compound, C31H27F3O7, is a liquid crystal and exhibits enanti-otropic SmA and nematic phase transitions. In the crystal, the the 2H-chromene ring system makes dihedral angles of 54.46 (17) and 7.79 (16)°, respectively, with the central benzene ring and 4-(hept-yloxy)benzene ring. The three F atoms of the -CF3 group are disordered over two sets of sites, with an occupancy ratio of 0.62 (3):0.38 (3). The crystal structre features two pairs of C-H⋯O hydrogen bonds, which form inversion dimers and generate R 2 (2)(10) and R 2 (2)(30) ring patterns. C-H⋯O inter-actions along [100] and C-H⋯π inter-actions futher consolidate the packing, leading to a three-dimensional network.

Related literature

For similar structures, see: Palakshamurthy, Sreenivasa et al. (2013 ▶), Palakshamurthy, Devarajegowda et al. (2013 ▶). For graph-set notation for hydrogen bonds, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C31H27F3O7

M = 568.53

Triclinic,

a = 5.6810 (3) Å

b = 16.036 (2) Å

c = 16.2954 (18) Å

α = 68.940 (12)°

β = 88.914 (6)°

γ = 88.486 (7)°

V = 1384.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.32 × 0.24 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.966, T max = 0.981

8822 measured reflections

4876 independent reflections

2837 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.104

wR(F 2) = 0.316

S = 0.99

4876 reflections

399 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2009 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813020679/kj2229sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020679/kj2229Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020679/kj2229Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C31H27F3O7	F(000) = 592
Mr = 568.53	Blocks
Triclinic, P1	Dx = 1.363 Mg m−3
Hall symbol: -P 1	Melting point: 434 K
a = 5.6810 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 16.036 (2) Å	Cell parameters from 2837 reflections
c = 16.2954 (18) Å	θ = 2.5–25°
α = 68.940 (12)°	µ = 0.11 mm−1
β = 88.914 (6)°	T = 296 K
γ = 88.486 (7)°	Block, colourless
V = 1384.8 (3) Å3	0.32 × 0.24 × 0.18 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	4876 independent reflections
Radiation source: fine-focus sealed tube	2837 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.079
Detector resolution: 1.03 pixels mm-1	θmax = 25.0°, θmin = 2.5°
phi and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −19→18
Tmin = 0.966, Tmax = 0.981	l = −19→17
8822 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.104	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.316	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.1918P)2] where P = (Fo2 + 2Fc2)/3
4876 reflections	(Δ/σ)max < 0.001
399 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.42 e Å−3
0 constraints

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	0.5018 (9)	1.1195 (3)	0.0428 (3)	0.0728 (13)
C2	0.4321 (7)	1.0781 (3)	0.1360 (3)	0.0538 (10)
C3	0.2160 (7)	1.1040 (3)	0.1631 (3)	0.0580 (10)
H3	0.1172	1.1448	0.1225	0.070*
C4	0.1518 (6)	1.0687 (2)	0.2499 (3)	0.0519 (10)
H4	0.0076	1.0854	0.2679	0.062*
C5	0.2991 (6)	1.0080 (2)	0.3119 (3)	0.0459 (9)
C6	0.5150 (6)	0.9843 (2)	0.2825 (3)	0.0470 (9)
C7	0.5806 (7)	1.0184 (3)	0.1946 (3)	0.0566 (10)
H7	0.7228	1.0009	0.1758	0.068*
C8	0.2469 (6)	0.9689 (2)	0.4027 (2)	0.0450 (9)
H8	0.1043	0.9838	0.4234	0.054*
C9	0.3928 (5)	0.9114 (2)	0.4601 (2)	0.0442 (8)
C10	0.6252 (6)	0.8895 (2)	0.4300 (3)	0.0485 (9)
C11	0.3301 (6)	0.8718 (2)	0.5537 (2)	0.0446 (8)
C12	0.3494 (6)	0.7435 (2)	0.6811 (3)	0.0465 (9)
C13	0.1534 (7)	0.6919 (3)	0.7119 (3)	0.0547 (10)
H13	0.0419	0.6868	0.6730	0.066*
C14	0.1256 (6)	0.6483 (3)	0.8005 (3)	0.0551 (10)
H14	−0.0056	0.6133	0.8222	0.066*
C15	0.2911 (6)	0.6561 (2)	0.8575 (3)	0.0506 (9)
C16	0.4882 (7)	0.7071 (3)	0.8258 (3)	0.0566 (10)
H16	0.6005	0.7120	0.8645	0.068*
C17	0.5167 (6)	0.7501 (3)	0.7371 (3)	0.0591 (11)
H17	0.6499	0.7838	0.7151	0.071*
C18	0.0998 (6)	0.6353 (3)	0.9943 (3)	0.0527 (10)
C19	0.1256 (6)	0.5916 (2)	1.0887 (3)	0.0481 (9)
C20	−0.0520 (6)	0.6051 (3)	1.1441 (3)	0.0552 (10)
H20	−0.1829	0.6408	1.1195	0.066*
C21	−0.0360 (6)	0.5673 (3)	1.2323 (3)	0.0579 (10)
H21	−0.1572	0.5764	1.2676	0.069*
C22	0.1589 (6)	0.5149 (2)	1.2712 (3)	0.0482 (9)
C23	0.3373 (6)	0.5008 (2)	1.2179 (3)	0.0521 (9)
H23	0.4680	0.4652	1.2430	0.062*
C24	0.3204 (6)	0.5393 (2)	1.1281 (2)	0.0491 (9)
H24	0.4419	0.5303	1.0930	0.059*
C25	0.3583 (7)	0.4275 (3)	1.4026 (3)	0.0586 (10)
H25A	0.4969	0.4643	1.3873	0.070*
H25B	0.3840	0.3777	1.3827	0.070*
C26	0.3225 (7)	0.3932 (3)	1.4994 (3)	0.0633 (11)
H26A	0.1929	0.3520	1.5147	0.076*
H26B	0.2803	0.4427	1.5181	0.076*
C27	0.5406 (8)	0.3461 (3)	1.5475 (3)	0.0638 (11)
H27A	0.5867	0.2993	1.5254	0.077*
H27B	0.6671	0.3886	1.5333	0.077*
C28	0.5177 (7)	0.3050 (3)	1.6459 (3)	0.0624 (11)
H28A	0.3880	0.2639	1.6609	0.075*
H28B	0.4810	0.3517	1.6691	0.075*
C29	0.7420 (8)	0.2550 (3)	1.6890 (3)	0.0666 (12)
H29A	0.7791	0.2093	1.6645	0.080*
H29B	0.8705	0.2966	1.6736	0.080*
C30	0.7303 (8)	0.2118 (3)	1.7865 (3)	0.0759 (14)
H30A	0.5981	0.1719	1.8024	0.091*
H30B	0.7017	0.2576	1.8116	0.091*
C31	0.9507 (10)	0.1598 (5)	1.8258 (4)	0.108 (2)
H31A	0.9800	0.1141	1.8014	0.162*
H31B	0.9312	0.1327	1.8884	0.162*
H31C	1.0814	0.1994	1.8125	0.162*
O1	0.6675 (4)	0.92522 (17)	0.34057 (18)	0.0549 (7)
O2	0.7777 (5)	0.8451 (2)	0.4762 (2)	0.0744 (10)
O3	0.2319 (5)	0.91399 (18)	0.5935 (2)	0.0646 (8)
O6	−0.0516 (5)	0.6888 (2)	0.9571 (2)	0.0797 (10)
F1	0.656 (4)	1.0696 (9)	0.0209 (8)	0.130 (5)	0.62 (3)
F2	0.600 (4)	1.1943 (10)	0.0239 (8)	0.120 (5)	0.62 (3)
F3	0.346 (2)	1.1281 (18)	−0.0147 (10)	0.139 (7)	0.62 (3)
F1A	0.364 (7)	1.091 (2)	−0.0042 (18)	0.149 (11)	0.38 (3)
F2A	0.731 (3)	1.100 (2)	0.0245 (10)	0.143 (11)	0.38 (3)
F3A	0.471 (6)	1.2076 (13)	0.0083 (16)	0.140 (10)	0.38 (3)
O4	0.3862 (5)	0.78518 (16)	0.59002 (17)	0.0557 (7)
O7	0.1577 (5)	0.47897 (19)	1.35995 (19)	0.0611 (8)
O5	0.2751 (4)	0.61051 (18)	0.94774 (17)	0.0576 (7)

	U11	U22	U33	U12	U13	U23
C1	0.088 (3)	0.074 (3)	0.056 (3)	−0.002 (3)	0.008 (3)	−0.023 (2)
C2	0.063 (2)	0.059 (2)	0.038 (2)	−0.0074 (18)	0.0065 (17)	−0.0160 (18)
C3	0.057 (2)	0.058 (2)	0.051 (3)	−0.0010 (18)	−0.0035 (18)	−0.0096 (19)
C4	0.0464 (19)	0.052 (2)	0.051 (2)	0.0005 (16)	0.0053 (16)	−0.0110 (17)
C5	0.0412 (17)	0.0395 (18)	0.054 (2)	−0.0005 (14)	0.0032 (15)	−0.0130 (16)
C6	0.0469 (19)	0.0453 (18)	0.047 (2)	0.0002 (15)	0.0064 (16)	−0.0154 (17)
C7	0.052 (2)	0.061 (2)	0.056 (3)	−0.0052 (18)	0.0122 (18)	−0.021 (2)
C8	0.0376 (17)	0.0443 (18)	0.050 (2)	0.0004 (14)	0.0087 (15)	−0.0137 (17)
C9	0.0366 (17)	0.0465 (19)	0.049 (2)	0.0017 (14)	0.0058 (15)	−0.0177 (16)
C10	0.0400 (18)	0.0465 (19)	0.051 (2)	0.0026 (15)	0.0101 (16)	−0.0080 (16)
C11	0.0453 (18)	0.0428 (18)	0.045 (2)	0.0025 (14)	0.0046 (15)	−0.0157 (16)
C12	0.052 (2)	0.0383 (17)	0.047 (2)	0.0065 (15)	0.0048 (16)	−0.0134 (16)
C13	0.056 (2)	0.057 (2)	0.048 (2)	−0.0072 (17)	−0.0036 (17)	−0.0152 (18)
C14	0.051 (2)	0.061 (2)	0.047 (2)	−0.0108 (17)	0.0033 (17)	−0.0123 (18)
C15	0.052 (2)	0.049 (2)	0.041 (2)	0.0089 (16)	0.0031 (16)	−0.0065 (16)
C16	0.050 (2)	0.063 (2)	0.055 (3)	0.0000 (17)	−0.0044 (17)	−0.0198 (19)
C17	0.053 (2)	0.052 (2)	0.069 (3)	−0.0066 (17)	0.0071 (19)	−0.018 (2)
C18	0.050 (2)	0.056 (2)	0.048 (2)	0.0028 (17)	0.0021 (17)	−0.0138 (18)
C19	0.0479 (19)	0.0474 (19)	0.043 (2)	0.0010 (15)	0.0024 (16)	−0.0100 (16)
C20	0.0459 (19)	0.062 (2)	0.053 (2)	0.0130 (17)	−0.0005 (17)	−0.0158 (19)
C21	0.050 (2)	0.071 (2)	0.050 (2)	0.0088 (18)	0.0098 (17)	−0.020 (2)
C22	0.0475 (19)	0.0475 (19)	0.046 (2)	−0.0013 (15)	0.0033 (16)	−0.0129 (16)
C23	0.0414 (18)	0.055 (2)	0.055 (3)	0.0092 (15)	−0.0008 (16)	−0.0157 (18)
C24	0.0448 (18)	0.058 (2)	0.041 (2)	0.0042 (15)	0.0044 (15)	−0.0146 (17)
C25	0.062 (2)	0.064 (2)	0.049 (3)	0.0108 (18)	0.0024 (18)	−0.0188 (19)
C26	0.073 (3)	0.069 (3)	0.045 (3)	0.003 (2)	0.004 (2)	−0.017 (2)
C27	0.072 (3)	0.062 (2)	0.056 (3)	0.007 (2)	0.000 (2)	−0.021 (2)
C28	0.074 (3)	0.066 (2)	0.044 (2)	0.008 (2)	0.002 (2)	−0.0174 (19)
C29	0.077 (3)	0.068 (3)	0.052 (3)	0.010 (2)	0.000 (2)	−0.021 (2)
C30	0.076 (3)	0.084 (3)	0.056 (3)	0.006 (2)	−0.003 (2)	−0.013 (2)
C31	0.088 (3)	0.150 (5)	0.066 (4)	0.036 (3)	−0.003 (3)	−0.017 (4)
O1	0.0460 (13)	0.0605 (16)	0.0526 (17)	0.0086 (11)	0.0122 (12)	−0.0149 (13)
O2	0.0458 (15)	0.082 (2)	0.072 (2)	0.0167 (14)	0.0041 (14)	−0.0008 (17)
O3	0.0740 (18)	0.0595 (16)	0.0583 (19)	0.0182 (13)	0.0114 (14)	−0.0206 (14)
O6	0.0733 (19)	0.097 (2)	0.059 (2)	0.0362 (17)	−0.0088 (15)	−0.0179 (17)
F1	0.161 (12)	0.120 (7)	0.103 (7)	0.017 (7)	0.066 (7)	−0.040 (5)
F2	0.191 (13)	0.085 (7)	0.077 (5)	−0.064 (8)	0.047 (7)	−0.018 (5)
F3	0.124 (7)	0.211 (18)	0.049 (4)	−0.048 (8)	−0.016 (4)	−0.002 (8)
F1A	0.26 (3)	0.142 (16)	0.059 (12)	−0.055 (13)	0.000 (11)	−0.048 (12)
F2A	0.077 (7)	0.23 (3)	0.047 (6)	0.004 (10)	0.025 (5)	0.041 (10)
F3A	0.194 (19)	0.086 (8)	0.089 (10)	0.059 (13)	0.059 (12)	0.026 (7)
O4	0.0720 (17)	0.0430 (14)	0.0482 (17)	0.0063 (12)	0.0114 (13)	−0.0126 (12)
O7	0.0623 (16)	0.0725 (18)	0.0451 (17)	0.0126 (13)	0.0021 (12)	−0.0179 (14)
O5	0.0637 (16)	0.0617 (16)	0.0388 (15)	0.0136 (12)	0.0025 (12)	−0.0089 (12)

C1—F2	1.268 (9)	C17—H17	0.9300
C1—F3	1.268 (14)	C18—O6	1.204 (4)
C1—F1	1.302 (12)	C18—O5	1.376 (5)
C1—F1A	1.31 (3)	C18—O5	1.376 (5)
C1—F3A	1.328 (17)	C18—C19	1.451 (5)
C1—F2A	1.379 (18)	C19—C24	1.390 (5)
C1—C2	1.473 (6)	C19—C20	1.405 (6)
C2—C7	1.368 (5)	C20—C21	1.349 (5)
C2—C3	1.399 (6)	C20—H20	0.9300
C3—C4	1.367 (6)	C21—C22	1.389 (5)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.397 (5)	C22—O7	1.351 (5)
C4—H4	0.9300	C22—C23	1.389 (6)
C5—C6	1.401 (5)	C23—C24	1.373 (5)
C5—C8	1.412 (5)	C23—H23	0.9300
C6—O1	1.373 (4)	C24—H24	0.9300
C6—C7	1.385 (5)	C25—O7	1.425 (4)
C7—H7	0.9300	C25—C26	1.484 (5)
C8—C9	1.334 (5)	C25—H25A	0.9700
C8—H8	0.9300	C25—H25B	0.9700
C9—C11	1.467 (5)	C26—C27	1.512 (6)
C9—C10	1.477 (5)	C26—H26A	0.9700
C10—O2	1.197 (4)	C26—H26B	0.9700
C10—O1	1.379 (5)	C27—C28	1.503 (6)
C11—O3	1.212 (5)	C27—H27A	0.9700
C11—O4	1.332 (4)	C27—H27B	0.9700
C12—C17	1.362 (5)	C28—C29	1.528 (6)
C12—C13	1.381 (5)	C28—H28A	0.9700
C12—O4	1.405 (4)	C28—H28B	0.9700
C13—C14	1.368 (5)	C29—C30	1.488 (6)
C13—H13	0.9300	C29—H29A	0.9700
C14—C15	1.372 (5)	C29—H29B	0.9700
C14—H14	0.9300	C30—C31	1.505 (7)
C15—C16	1.383 (5)	C30—H30A	0.9700
C15—O5	1.390 (4)	C30—H30B	0.9700
C15—O5	1.390 (4)	C31—H31A	0.9600
C16—C17	1.368 (6)	C31—H31B	0.9600
C16—H16	0.9300	C31—H31C	0.9600
F2—C1—F3	107.6 (10)	O6—C18—O5	121.0 (4)
F2—C1—F1	104.7 (8)	O6—C18—C19	126.5 (4)
F3—C1—F1	100.0 (12)	O5—C18—C19	112.5 (3)
F2—C1—F1A	130.1 (13)	O5—C18—C19	112.5 (3)
F1—C1—F1A	82.3 (17)	C24—C19—C20	117.6 (4)
F3—C1—F3A	77.9 (13)	C24—C19—C18	123.9 (4)
F1—C1—F3A	128.4 (10)	C20—C19—C18	118.5 (3)
F1A—C1—F3A	103.1 (17)	C21—C20—C19	121.2 (3)
F2—C1—F2A	77.5 (10)	C21—C20—H20	119.4
F3—C1—F2A	118.2 (12)	C19—C20—H20	119.4
F1A—C1—F2A	107.4 (19)	C20—C21—C22	120.9 (4)
F3A—C1—F2A	107.3 (12)	C20—C21—H21	119.6
F2—C1—C2	114.1 (6)	C22—C21—H21	119.6
F3—C1—C2	117.8 (8)	O7—C22—C23	124.3 (3)
F1—C1—C2	111.0 (6)	O7—C22—C21	116.5 (3)
F1A—C1—C2	108.6 (14)	C23—C22—C21	119.1 (4)
F3A—C1—C2	115.2 (10)	C24—C23—C22	119.9 (3)
F2A—C1—C2	114.4 (7)	C24—C23—H23	120.1
C7—C2—C3	121.3 (4)	C22—C23—H23	120.1
C7—C2—C1	120.2 (4)	C23—C24—C19	121.4 (4)
C3—C2—C1	118.4 (4)	C23—C24—H24	119.3
C4—C3—C2	119.3 (3)	C19—C24—H24	119.3
C4—C3—H3	120.3	O7—C25—C26	110.2 (3)
C2—C3—H3	120.3	O7—C25—H25A	109.6
C3—C4—C5	121.1 (4)	C26—C25—H25A	109.6
C3—C4—H4	119.4	O7—C25—H25B	109.6
C5—C4—H4	119.4	C26—C25—H25B	109.6
C4—C5—C6	118.0 (4)	H25A—C25—H25B	108.1
C4—C5—C8	124.7 (3)	C25—C26—C27	111.9 (4)
C6—C5—C8	117.3 (3)	C25—C26—H26A	109.2
O1—C6—C7	117.9 (3)	C27—C26—H26A	109.2
O1—C6—C5	120.6 (3)	C25—C26—H26B	109.2
C7—C6—C5	121.5 (3)	C27—C26—H26B	109.2
C2—C7—C6	118.7 (4)	H26A—C26—H26B	107.9
C2—C7—H7	120.7	C28—C27—C26	115.8 (4)
C6—C7—H7	120.7	C28—C27—H27A	108.3
C9—C8—C5	123.0 (3)	C26—C27—H27A	108.3
C9—C8—H8	118.5	C28—C27—H27B	108.3
C5—C8—H8	118.5	C26—C27—H27B	108.3
C8—C9—C11	121.1 (3)	H27A—C27—H27B	107.4
C8—C9—C10	119.8 (3)	C27—C28—C29	112.5 (4)
C11—C9—C10	119.1 (3)	C27—C28—H28A	109.1
O2—C10—O1	118.2 (3)	C29—C28—H28A	109.1
O2—C10—C9	125.7 (4)	C27—C28—H28B	109.1
O1—C10—C9	116.0 (3)	C29—C28—H28B	109.1
O3—C11—O4	123.4 (4)	H28A—C28—H28B	107.8
O3—C11—C9	122.8 (3)	C30—C29—C28	115.2 (4)
O4—C11—C9	113.7 (3)	C30—C29—H29A	108.5
C17—C12—C13	121.2 (4)	C28—C29—H29A	108.5
C17—C12—O4	119.0 (3)	C30—C29—H29B	108.5
C13—C12—O4	119.7 (3)	C28—C29—H29B	108.5
C14—C13—C12	119.1 (3)	H29A—C29—H29B	107.5
C14—C13—H13	120.5	C29—C30—C31	113.4 (5)
C12—C13—H13	120.5	C29—C30—H30A	108.9
C13—C14—C15	120.1 (3)	C31—C30—H30A	108.9
C13—C14—H14	120.0	C29—C30—H30B	108.9
C15—C14—H14	120.0	C31—C30—H30B	108.9
C14—C15—C16	120.4 (4)	H30A—C30—H30B	107.7
C14—C15—O5	122.2 (3)	C30—C31—H31A	109.5
C16—C15—O5	117.3 (3)	C30—C31—H31B	109.5
C14—C15—O5	122.2 (3)	H31A—C31—H31B	109.5
C16—C15—O5	117.3 (3)	C30—C31—H31C	109.5
C17—C16—C15	119.5 (4)	H31A—C31—H31C	109.5
C17—C16—H16	120.3	H31B—C31—H31C	109.5
C15—C16—H16	120.3	C6—O1—C10	123.1 (3)
C12—C17—C16	119.8 (3)	C11—O4—C12	117.5 (3)
C12—C17—H17	120.1	C22—O7—C25	118.3 (3)
C16—C17—H17	120.1	C18—O5—C15	118.6 (3)
O6—C18—O5	121.0 (4)
F2—C1—C2—C7	−93.5 (14)	O5—C15—C16—C17	177.2 (3)
F3—C1—C2—C7	139.0 (15)	C13—C12—C17—C16	−1.9 (6)
F1—C1—C2—C7	24.5 (13)	O4—C12—C17—C16	−177.4 (3)
F1A—C1—C2—C7	113 (2)	C15—C16—C17—C12	1.0 (6)
F3A—C1—C2—C7	−132 (2)	O6—C18—C19—C24	−171.3 (4)
F2A—C1—C2—C7	−6.8 (19)	O5—C18—C19—C24	7.5 (5)
F2—C1—C2—C3	84.1 (14)	O5—C18—C19—C24	7.5 (5)
F3—C1—C2—C3	−43.4 (16)	O6—C18—C19—C20	6.4 (6)
F1—C1—C2—C3	−157.9 (12)	O5—C18—C19—C20	−174.8 (3)
F1A—C1—C2—C3	−69 (2)	O5—C18—C19—C20	−174.8 (3)
F3A—C1—C2—C3	46 (2)	C24—C19—C20—C21	−1.3 (6)
F2A—C1—C2—C3	170.8 (19)	C18—C19—C20—C21	−179.1 (3)
C7—C2—C3—C4	−0.2 (6)	C19—C20—C21—C22	1.1 (6)
C1—C2—C3—C4	−177.7 (4)	C20—C21—C22—O7	−179.2 (3)
C2—C3—C4—C5	0.6 (6)	C20—C21—C22—C23	−0.9 (6)
C3—C4—C5—C6	0.0 (5)	O7—C22—C23—C24	179.1 (3)
C3—C4—C5—C8	179.7 (3)	C21—C22—C23—C24	0.8 (6)
C4—C5—C6—O1	179.7 (3)	C22—C23—C24—C19	−1.1 (6)
C8—C5—C6—O1	0.0 (5)	C20—C19—C24—C23	1.3 (5)
C4—C5—C6—C7	−1.1 (5)	C18—C19—C24—C23	178.9 (3)
C8—C5—C6—C7	179.2 (3)	O7—C25—C26—C27	−174.3 (3)
C3—C2—C7—C6	−0.9 (6)	C25—C26—C27—C28	−177.1 (3)
C1—C2—C7—C6	176.6 (4)	C26—C27—C28—C29	177.3 (4)
O1—C6—C7—C2	−179.3 (3)	C27—C28—C29—C30	−179.4 (4)
C5—C6—C7—C2	1.6 (6)	C28—C29—C30—C31	177.3 (5)
C4—C5—C8—C9	−179.7 (3)	C7—C6—O1—C10	177.5 (3)
C6—C5—C8—C9	0.0 (5)	C5—C6—O1—C10	−3.3 (5)
C5—C8—C9—C11	−179.5 (3)	O2—C10—O1—C6	−173.3 (3)
C5—C8—C9—C10	2.8 (5)	C9—C10—O1—C6	5.9 (5)
C8—C9—C10—O2	173.4 (4)	O3—C11—O4—C12	−6.4 (5)
C11—C9—C10—O2	−4.3 (6)	C9—C11—O4—C12	175.1 (3)
C8—C9—C10—O1	−5.6 (5)	C17—C12—O4—C11	−83.4 (4)
C11—C9—C10—O1	176.7 (3)	C13—C12—O4—C11	101.0 (4)
C8—C9—C11—O3	−40.1 (5)	C23—C22—O7—C25	4.0 (5)
C10—C9—C11—O3	137.6 (4)	C21—C22—O7—C25	−177.7 (3)
C8—C9—C11—O4	138.4 (3)	C26—C25—O7—C22	−179.4 (3)
C10—C9—C11—O4	−43.9 (4)	O6—C18—O5—O5	0.0 (10)
C17—C12—C13—C14	1.4 (6)	C19—C18—O5—O5	0.0 (9)
O4—C12—C13—C14	176.9 (3)	O6—C18—O5—C15	7.6 (6)
C12—C13—C14—C15	0.0 (6)	O5—C18—O5—C15	0 (100)
C13—C14—C15—C16	−0.8 (6)	C19—C18—O5—C15	−171.3 (3)
C13—C14—C15—O5	−177.5 (4)	C16—C15—O5—O5	0.0 (8)
C13—C14—C15—O5	−177.5 (4)	C14—C15—O5—C18	−69.4 (5)
C14—C15—C16—C17	0.4 (6)	C16—C15—O5—C18	113.8 (4)
O5—C15—C16—C17	177.2 (3)	O5—C15—O5—C18	0 (100)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O6i	0.93	2.53	3.313 (5)	142
C8—H8···O3i	0.93	2.44	3.277 (4)	150
C16—H16···O6ii	0.93	2.45	3.350 (5)	163
C24—H24···O5	0.93	2.45	2.759 (5)	100
C14—H14···Cg2iii	0.93	2.81	3.517 (5)	133
C23—H23···Cg1iv	0.93	2.94	3.650 (5)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C12–C17 and C19–C24 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O6i	0.93	2.53	3.313 (5)	142
C8—H8⋯O3i	0.93	2.44	3.277 (4)	150
C16—H16⋯O6ii	0.93	2.45	3.350 (5)	163
C14—H14⋯Cg2iii	0.93	2.81	3.517 (5)	133
C23—H23⋯Cg1iv	0.93	2.94	3.650 (5)	134

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .