1,2-Bis(2-ethyl-5-hydroxy­methyl-3-thien­yl)-3,3,4,4,5,5-hexa­fluoro­cyclo­pent-1-ene, a new photochromic diaryl­ethene compound

The title compound, C₁₉H₁₈F₆O₂S₂, is one of the most promising materials for optical memories and other optoelectronic devices. The mol­ecular structure has a photoactive anti­parallel conformation. The dihedral angles between the cyclo­pentene ring and the attached thio­phene rings are 52.12 (1) and 52.70 (1)°. The distance between the two reactive C atoms, i.e. the ring C atoms to which the ethyl groups are attached, is 3.596 (4) Å. A dichloro­methane solution of the colorless crystals turns pink when exposed to UV radiation, with an absorption maximum of 542 nm.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.051
• wR factor = 0.157
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H1A    ..  H7'C    ..       1.99 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.67 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.03 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C13'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18
PLAT301_ALERT_3_C Main Residue  Disorder .........................      12.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C4     -   C5     ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C11    -   C12    ...       1.36 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

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

1,2-Bis(2-ethyl-5-hydroxymethyl-3-thienyl)-3,3,4,4,5,5- hexafluorocyclopent-1-ene

Crystal data

C19H18F6O2S2	F(000) = 936
Mr = 456.45	Dx = 1.466 Mg m^−3
Monoclinic, P21/c	Melting point: 399 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.902 (2) Å	Cell parameters from 3152 reflections
b = 8.6229 (14) Å	θ = 2.5–24.1°
c = 18.972 (3) Å	µ = 0.32 mm^−1
β = 101.588 (3)°	T = 294 K
V = 2067.7 (6) Å^3	Prism, colorless
Z = 4	0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	4208 independent reflections
Radiation source: fine-focus sealed tube	2538 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 26.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→16
Tmin = 0.932, Tmax = 0.944	k = −8→10
11247 measured reflections	l = −23→23

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.157	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0723P)^2 + 1.0406P] where P = (Fo^2 + 2Fc^2)/3
4208 reflections	(Δ/σ)max = 0.001
288 parameters	Δρmax = 0.43 e Å^−3
28 restraints	Δρmin = −0.34 e Å^−3

Special details

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	Occ. (<1)
S1	0.42994 (6)	0.36837 (12)	0.55806 (4)	0.0630 (3)
S2	0.29649 (8)	0.65954 (11)	0.28693 (5)	0.0682 (3)
O1	0.4200 (2)	0.3889 (3)	0.72526 (13)	0.0705 (7)
H1	0.469 (3)	0.436 (5)	0.751 (2)	0.089 (14)*
O2	0.43077 (18)	0.4266 (3)	0.19092 (12)	0.0612 (6)
H2A	0.434 (4)	0.332 (6)	0.205 (2)	0.099 (17)*
C1	0.3611 (3)	0.4963 (5)	0.67693 (17)	0.0736 (10)
H1A	0.4021	0.5904	0.6762	0.088*
H1B	0.2967	0.5230	0.6932	0.088*
C2	0.3335 (3)	0.4298 (4)	0.60240 (16)	0.0567 (8)
C3	0.2367 (3)	0.4112 (4)	0.56102 (16)	0.0550 (8)
H3A	0.1746	0.4357	0.5764	0.066*
C4	0.2382 (2)	0.3506 (4)	0.49141 (15)	0.0472 (7)
C5	0.3386 (2)	0.3206 (4)	0.48194 (15)	0.0528 (8)
C6	0.3740 (3)	0.2535 (6)	0.41797 (19)	0.0793 (12)	0.80
H6A	0.3199	0.1824	0.3941	0.095*	0.80
H6B	0.3790	0.3369	0.3845	0.095*	0.80
C7	0.4758 (4)	0.1707 (8)	0.4333 (3)	0.1006 (19)	0.80
H7A	0.4916	0.1321	0.3892	0.151*	0.80
H7B	0.4715	0.0856	0.4652	0.151*	0.80
H7C	0.5307	0.2405	0.4556	0.151*	0.80
C6'	0.3740 (3)	0.2535 (6)	0.41797 (19)	0.0793 (12)	0.20
H6'A	0.3194	0.2847	0.3775	0.095*	0.20
H6'B	0.3650	0.1426	0.4228	0.095*	0.20
C7'	0.4750 (14)	0.268 (4)	0.3903 (14)	0.120 (9)	0.20
H7'A	0.4677	0.2143	0.3453	0.180*	0.20
H7'B	0.5322	0.2237	0.4246	0.180*	0.20
H7'C	0.4894	0.3757	0.3835	0.180*	0.20
C8	0.3234 (3)	0.4729 (4)	0.17112 (16)	0.0593 (8)
H8A	0.2844	0.3947	0.1398	0.071*
H8B	0.3194	0.5691	0.1442	0.071*
C9	0.2723 (2)	0.4956 (4)	0.23451 (15)	0.0527 (8)
C10	0.2087 (2)	0.3975 (4)	0.26192 (15)	0.0518 (8)
H10A	0.1858	0.3029	0.2408	0.062*
C11	0.1803 (2)	0.4528 (4)	0.32620 (15)	0.0492 (7)
C12	0.2216 (3)	0.5949 (4)	0.34633 (17)	0.0587 (8)
C13	0.2054 (5)	0.6936 (5)	0.4079 (3)	0.1038 (16)	0.65
H13A	0.1313	0.6884	0.4109	0.125*	0.65
H13B	0.2460	0.6497	0.4519	0.125*	0.65
C14	0.2352 (8)	0.8595 (8)	0.4042 (5)	0.125 (3)	0.65
H14A	0.2198	0.9138	0.4450	0.188*	0.65
H14B	0.1957	0.9048	0.3608	0.188*	0.65
H14C	0.3095	0.8671	0.4044	0.188*	0.65
C13'	0.2054 (5)	0.6936 (5)	0.4079 (3)	0.1038 (16)	0.35
H13C	0.1515	0.7688	0.3879	0.125*	0.35
H13D	0.1739	0.6266	0.4389	0.125*	0.35
C14'	0.2876 (10)	0.780 (2)	0.4547 (8)	0.116 (5)	0.35
H14D	0.2577	0.8347	0.4897	0.173*	0.35
H14E	0.3190	0.8519	0.4267	0.173*	0.35
H14F	0.3407	0.7090	0.4787	0.173*	0.35
C15	0.1413 (2)	0.3212 (4)	0.43753 (16)	0.0506 (7)
C16	0.0517 (3)	0.2370 (5)	0.45942 (19)	0.0733 (11)
C17	−0.0242 (3)	0.1983 (6)	0.3890 (2)	0.0756 (11)
C18	0.0087 (3)	0.3049 (5)	0.33396 (19)	0.0720 (10)
C19	0.1173 (2)	0.3615 (4)	0.36814 (16)	0.0512 (7)
F1	0.0011 (2)	0.3259 (4)	0.50087 (15)	0.1194 (11)
F2	0.0842 (2)	0.1098 (4)	0.49826 (14)	0.1186 (11)
F3	−0.0117 (2)	0.0511 (4)	0.37151 (14)	0.1183 (10)
F4	−0.12570 (18)	0.2148 (4)	0.39389 (15)	0.1208 (10)
F5	−0.06054 (18)	0.4274 (4)	0.32114 (15)	0.1153 (10)
F6	0.0024 (2)	0.2376 (4)	0.27063 (12)	0.1200 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0531 (5)	0.0866 (7)	0.0474 (4)	0.0017 (4)	0.0053 (3)	−0.0056 (4)
S2	0.0891 (7)	0.0565 (5)	0.0651 (5)	−0.0137 (5)	0.0301 (5)	0.0037 (4)
O1	0.0821 (18)	0.0699 (17)	0.0514 (13)	−0.0092 (14)	−0.0064 (12)	−0.0052 (12)
O2	0.0564 (14)	0.0682 (17)	0.0606 (14)	−0.0063 (12)	0.0154 (10)	−0.0018 (12)
C1	0.082 (2)	0.081 (3)	0.0522 (19)	0.011 (2)	0.0002 (17)	−0.0153 (18)
C2	0.065 (2)	0.058 (2)	0.0458 (16)	0.0060 (16)	0.0099 (15)	−0.0047 (15)
C3	0.0566 (19)	0.065 (2)	0.0456 (16)	0.0064 (16)	0.0159 (14)	−0.0019 (15)
C4	0.0491 (17)	0.0530 (18)	0.0410 (15)	−0.0045 (14)	0.0125 (12)	0.0019 (13)
C5	0.0532 (18)	0.064 (2)	0.0422 (16)	−0.0030 (15)	0.0111 (13)	−0.0023 (14)
C6	0.062 (2)	0.121 (4)	0.056 (2)	0.014 (2)	0.0145 (17)	−0.017 (2)
C7	0.096 (4)	0.127 (5)	0.081 (3)	0.037 (4)	0.021 (3)	−0.022 (3)
C6'	0.062 (2)	0.121 (4)	0.056 (2)	0.014 (2)	0.0145 (17)	−0.017 (2)
C7'	0.121 (12)	0.118 (12)	0.114 (12)	−0.008 (9)	0.005 (9)	0.000 (9)
C8	0.060 (2)	0.073 (2)	0.0435 (16)	−0.0050 (17)	0.0081 (14)	0.0076 (15)
C9	0.0532 (18)	0.062 (2)	0.0416 (15)	−0.0007 (15)	0.0069 (13)	0.0082 (14)
C10	0.0496 (17)	0.062 (2)	0.0419 (15)	−0.0052 (15)	0.0042 (13)	0.0013 (14)
C11	0.0460 (16)	0.0556 (19)	0.0456 (16)	−0.0028 (14)	0.0085 (13)	0.0042 (14)
C12	0.072 (2)	0.054 (2)	0.0556 (18)	−0.0023 (17)	0.0254 (16)	0.0030 (15)
C13	0.172 (5)	0.064 (3)	0.095 (3)	−0.018 (3)	0.073 (3)	−0.021 (2)
C14	0.175 (7)	0.087 (5)	0.121 (6)	0.011 (5)	0.045 (5)	−0.030 (4)
C13'	0.172 (5)	0.064 (3)	0.095 (3)	−0.018 (3)	0.073 (3)	−0.021 (2)
C14'	0.114 (8)	0.131 (9)	0.107 (8)	0.006 (7)	0.033 (7)	−0.014 (7)
C15	0.0453 (16)	0.0593 (19)	0.0497 (17)	−0.0062 (14)	0.0156 (13)	−0.0023 (14)
C16	0.067 (2)	0.095 (3)	0.061 (2)	−0.025 (2)	0.0204 (18)	0.005 (2)
C17	0.057 (2)	0.097 (3)	0.075 (2)	−0.033 (2)	0.0172 (18)	−0.005 (2)
C18	0.051 (2)	0.102 (3)	0.062 (2)	−0.012 (2)	0.0065 (16)	−0.003 (2)
C19	0.0444 (16)	0.061 (2)	0.0494 (17)	−0.0084 (15)	0.0129 (13)	−0.0036 (15)
F1	0.0806 (15)	0.198 (3)	0.0947 (16)	−0.0471 (18)	0.0534 (13)	−0.0487 (19)
F2	0.113 (2)	0.133 (2)	0.1015 (18)	−0.0593 (18)	0.0011 (15)	0.0506 (17)
F3	0.148 (2)	0.098 (2)	0.1033 (19)	−0.0436 (19)	0.0105 (17)	−0.0141 (16)
F4	0.0587 (14)	0.198 (3)	0.1078 (19)	−0.0358 (17)	0.0229 (12)	0.005 (2)
F5	0.0599 (14)	0.144 (3)	0.133 (2)	−0.0030 (15)	−0.0018 (13)	0.040 (2)
F6	0.0988 (17)	0.196 (3)	0.0650 (14)	−0.0768 (19)	0.0166 (13)	−0.0351 (17)

Geometric parameters (Å, º)

S1—C2	1.720 (3)	C8—H8B	0.9700
S1—C5	1.720 (3)	C9—C10	1.353 (4)
S2—C12	1.718 (3)	C10—C11	1.425 (4)
S2—C9	1.721 (3)	C10—H10A	0.9300
O1—C1	1.413 (4)	C11—C12	1.360 (4)
O1—H1	0.82 (4)	C11—C19	1.474 (4)
O2—C8	1.418 (4)	C12—C13	1.493 (5)
O2—H2A	0.85 (5)	C13—C14	1.487 (7)
C1—C2	1.501 (4)	C13—H13A	0.9700
C1—H1A	0.9700	C13—H13B	0.9700
C1—H1B	0.9700	C14—H14A	0.9600
C2—C3	1.344 (4)	C14—H14B	0.9600
C3—C4	1.424 (4)	C14—H14C	0.9600
C3—H3A	0.9300	C14'—H14D	0.9600
C4—C5	1.368 (4)	C14'—H14E	0.9600
C4—C15	1.469 (4)	C14'—H14F	0.9600
C5—C6	1.496 (4)	C15—C19	1.337 (4)
C6—C7	1.472 (5)	C15—C16	1.493 (4)
C6—H6A	0.9700	C16—F2	1.341 (5)
C6—H6B	0.9700	C16—F1	1.356 (5)
C7—H7A	0.9600	C16—C17	1.526 (5)
C7—H7B	0.9600	C17—F3	1.330 (5)
C7—H7C	0.9600	C17—F4	1.338 (4)
C7'—H7'A	0.9600	C17—C18	1.515 (5)
C7'—H7'B	0.9600	C18—F6	1.322 (4)
C7'—H7'C	0.9600	C18—F5	1.373 (5)
C8—C9	1.496 (4)	C18—C19	1.502 (5)
C8—H8A	0.9700
C2—S1—C5	92.50 (15)	C9—C10—H10A	123.2
C12—S2—C9	92.98 (15)	C11—C10—H10A	123.2
C1—O1—H1	108 (3)	C12—C11—C10	112.8 (3)
C8—O2—H2A	110 (3)	C12—C11—C19	123.9 (3)
O1—C1—C2	110.8 (3)	C10—C11—C19	123.2 (3)
O1—C1—H1A	109.5	C11—C12—C13	128.6 (3)
C2—C1—H1A	109.5	C11—C12—S2	110.4 (2)
O1—C1—H1B	109.5	C13—C12—S2	120.9 (3)
C2—C1—H1B	109.5	C14—C13—C12	115.7 (4)
H1A—C1—H1B	108.1	C14—C13—H13A	108.4
C3—C2—C1	127.8 (3)	C12—C13—H13A	108.4
C3—C2—S1	110.9 (2)	C14—C13—H13B	108.4
C1—C2—S1	121.4 (3)	C12—C13—H13B	108.4
C2—C3—C4	113.7 (3)	H13A—C13—H13B	107.4
C2—C3—H3A	123.2	C13—C14—H14A	109.5
C4—C3—H3A	123.2	C13—C14—H14B	109.5
C5—C4—C3	112.4 (3)	H14A—C14—H14B	109.5
C5—C4—C15	124.9 (3)	C13—C14—H14C	109.5
C3—C4—C15	122.8 (3)	H14A—C14—H14C	109.5
C4—C5—C6	129.1 (3)	H14B—C14—H14C	109.5
C4—C5—S1	110.6 (2)	H14D—C14'—H14E	109.5
C6—C5—S1	120.3 (2)	H14D—C14'—H14F	109.5
C7—C6—C5	115.6 (3)	H14E—C14'—H14F	109.5
C7—C6—H6A	108.4	C19—C15—C4	129.6 (3)
C5—C6—H6A	108.4	C19—C15—C16	111.2 (3)
C7—C6—H6B	108.4	C4—C15—C16	119.2 (3)
C5—C6—H6B	108.4	F2—C16—F1	106.1 (3)
H6A—C6—H6B	107.4	F2—C16—C15	112.1 (3)
C6—C7—H7A	109.5	F1—C16—C15	112.2 (3)
C6—C7—H7B	109.5	F2—C16—C17	112.1 (4)
H7A—C7—H7B	109.5	F1—C16—C17	109.4 (3)
C6—C7—H7C	109.5	C15—C16—C17	105.1 (3)
H7A—C7—H7C	109.5	F3—C17—F4	106.8 (3)
H7B—C7—H7C	109.5	F3—C17—C18	110.0 (3)
H7'A—C7'—H7'B	109.5	F4—C17—C18	113.4 (4)
H7'A—C7'—H7'C	109.5	F3—C17—C16	109.8 (4)
H7'B—C7'—H7'C	109.5	F4—C17—C16	112.4 (3)
O2—C8—C9	112.9 (2)	C18—C17—C16	104.5 (3)
O2—C8—H8A	109.0	F6—C18—F5	104.9 (3)
C9—C8—H8A	109.0	F6—C18—C19	114.7 (3)
O2—C8—H8B	109.0	F5—C18—C19	110.1 (3)
C9—C8—H8B	109.0	F6—C18—C17	112.7 (4)
H8A—C8—H8B	107.8	F5—C18—C17	109.0 (3)
C10—C9—C8	128.8 (3)	C19—C18—C17	105.4 (3)
C10—C9—S2	110.2 (2)	C15—C19—C11	128.8 (3)
C8—C9—S2	120.9 (2)	C15—C19—C18	110.6 (3)
C9—C10—C11	113.6 (3)	C11—C19—C18	120.5 (3)
O1—C1—C2—C3	122.6 (4)	C4—C15—C16—F2	−46.8 (4)
O1—C1—C2—S1	−58.5 (4)	C19—C15—C16—F1	−106.4 (3)
C5—S1—C2—C3	1.2 (3)	C4—C15—C16—F1	72.4 (4)
C5—S1—C2—C1	−177.9 (3)	C19—C15—C16—C17	12.3 (4)
C1—C2—C3—C4	177.4 (3)	C4—C15—C16—C17	−168.8 (3)
S1—C2—C3—C4	−1.6 (4)	F2—C16—C17—F3	−21.5 (4)
C2—C3—C4—C5	1.4 (4)	F1—C16—C17—F3	−138.9 (3)
C2—C3—C4—C15	−180.0 (3)	C15—C16—C17—F3	100.5 (4)
C3—C4—C5—C6	178.4 (4)	F2—C16—C17—F4	97.2 (4)
C15—C4—C5—C6	−0.2 (6)	F1—C16—C17—F4	−20.2 (5)
C3—C4—C5—S1	−0.4 (3)	C15—C16—C17—F4	−140.8 (4)
C15—C4—C5—S1	−179.1 (3)	F2—C16—C17—C18	−139.4 (4)
C2—S1—C5—C4	−0.4 (3)	F1—C16—C17—C18	103.2 (4)
C2—S1—C5—C6	−179.4 (3)	C15—C16—C17—C18	−17.4 (4)
C4—C5—C6—C7	−153.1 (5)	F3—C17—C18—F6	24.5 (5)
S1—C5—C6—C7	25.6 (6)	F4—C17—C18—F6	−95.0 (4)
O2—C8—C9—C10	−99.2 (4)	C16—C17—C18—F6	142.3 (4)
O2—C8—C9—S2	77.1 (4)	F3—C17—C18—F5	140.5 (3)
C12—S2—C9—C10	0.5 (3)	F4—C17—C18—F5	21.1 (5)
C12—S2—C9—C8	−176.5 (3)	C16—C17—C18—F5	−101.7 (4)
C8—C9—C10—C11	175.7 (3)	F3—C17—C18—C19	−101.3 (4)
S2—C9—C10—C11	−0.9 (3)	F4—C17—C18—C19	139.2 (3)
C9—C10—C11—C12	1.0 (4)	C16—C17—C18—C19	16.5 (4)
C9—C10—C11—C19	−176.0 (3)	C4—C15—C19—C11	−2.5 (6)
C10—C11—C12—C13	176.6 (4)	C16—C15—C19—C11	176.3 (3)
C19—C11—C12—C13	−6.4 (6)	C4—C15—C19—C18	179.6 (3)
C10—C11—C12—S2	−0.6 (4)	C16—C15—C19—C18	−1.7 (4)
C19—C11—C12—S2	176.3 (2)	C12—C11—C19—C15	−52.8 (5)
C9—S2—C12—C11	0.1 (3)	C10—C11—C19—C15	123.9 (4)
C9—S2—C12—C13	−177.4 (4)	C12—C11—C19—C18	125.0 (4)
C11—C12—C13—C14	−163.2 (6)	C10—C11—C19—C18	−58.3 (4)
S2—C12—C13—C14	13.8 (8)	F6—C18—C19—C15	−134.3 (4)
C5—C4—C15—C19	−50.0 (5)	F5—C18—C19—C15	107.7 (3)
C3—C4—C15—C19	131.5 (4)	C17—C18—C19—C15	−9.7 (4)
C5—C4—C15—C16	131.3 (4)	F6—C18—C19—C11	47.6 (5)
C3—C4—C15—C16	−47.2 (5)	F5—C18—C19—C11	−70.4 (4)
C19—C15—C16—F2	134.3 (3)	C17—C18—C19—C11	172.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82 (4)	1.93 (4)	2.745 (4)	171 (4)
O2—H2A···O1^ii	0.85 (5)	1.96 (5)	2.807 (4)	170 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2.