(E)-4-Meth-oxy-2-[3-(trifluoro-meth-yl)phenyl-imino-meth-yl]phenol.

The title compound, C(15)H(12)F(3)NO(2), adopts the phenol-imine tautomeric form, with the H atom attached to oxygen rather than to nitro-gen. There are two independent mol-ecules aligned nearly parallel in the asymmetric unit with their trifloramethyl groups pointing in opposite directions. The dihedral angles between the aromatic rings are 40.43 (1)° in the first mol-ecule and 36.12 (1)° in the second. Strong intra-molecular O-H⋯N hydrogen bonding generates S(6) ring motifs. Weak inter-molecular C-H⋯O hydrogen bonds link the independent mol-ecules separately into sheets normal to [010]. In addition, C-H⋯π inter-actions are also observed. The F atoms of the trifluoro-methyl groups are disordered over two sets of sites with refined site occupancies of 0.59 (2)/0.41 (2) and 0.62 (3)/0.38 (3), respectively.

Related literature

For the photochromic and thermochromic characteristics of Schiff base compounds, see: Williams (1972 ▶); Calligaris et al. (1972 ▶); Gavronic et al. (1996 ▶); Hadjoudis et al. (1987 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Temel et al. (2007 ▶); Odabaşoğlu & Büyükgüngör (2006 ▶).

Experimental

Crystal data

C15H12F3NO2

M = 295.26

Monoclinic,

a = 13.4771 (7) Å

b = 6.4526 (2) Å

c = 31.7097 (15) Å

β = 92.647 (4)°

V = 2754.6 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.80 × 0.43 × 0.15 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.739, T max = 0.944

23526 measured reflections

5197 independent reflections

3536 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.205

S = 1.07

5197 reflections

444 parameters

144 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680905034X/si2222sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905034X/si2222Isup2.hkl

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

C15H12F3NO2	F(000) = 1216
Mr = 295.26	Dx = 1.424 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 20067 reflections
a = 13.4771 (7) Å	θ = 1.3–25.7°
b = 6.4526 (2) Å	µ = 0.12 mm−1
c = 31.7097 (15) Å	T = 296 K
β = 92.647 (4)°	Prism, yellow
V = 2754.6 (2) Å3	0.80 × 0.43 × 0.15 mm
Z = 8

Stoe IPDS II diffractometer	5197 independent reflections
Radiation source: fine-focus sealed tube	3536 reflections with I > 2σ(I)
plane graphite	Rint = 0.075
Detector resolution: 6.67 pixels mm-1	θmax = 25.7°, θmin = 1.3°
rotation method scans	h = −16→16
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −7→7
Tmin = 0.739, Tmax = 0.944	l = −38→38
23526 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)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.205	w = 1/[σ2(Fo2) + (0.0875P)2 + 1.1131P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
5197 reflections	Δρmax = 0.20 e Å−3
444 parameters	Δρmin = −0.25 e Å−3
144 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: 0.0018 (5)

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)
F1A	0.1216 (9)	0.4505 (8)	0.46713 (17)	0.126 (3)	0.592 (15)
F2A	0.1877 (10)	0.1908 (17)	0.5018 (2)	0.155 (4)	0.592 (15)
F3A	0.0307 (7)	0.218 (2)	0.4785 (4)	0.187 (5)	0.592 (15)
F1B	0.1963 (14)	0.406 (2)	0.4751 (4)	0.165 (5)	0.408 (15)
F2B	0.1215 (13)	0.1269 (16)	0.5008 (3)	0.126 (4)	0.408 (15)
F3B	0.0359 (10)	0.324 (3)	0.4722 (6)	0.181 (6)	0.408 (15)
C1A	0.61622 (19)	0.2839 (4)	0.27472 (8)	0.0492 (6)
C2A	0.6470 (2)	0.4936 (5)	0.27532 (9)	0.0522 (7)
C3A	0.6768 (2)	0.5824 (5)	0.31314 (9)	0.0596 (7)
H3A	0.6973	0.7201	0.3137	0.072*
C4A	0.6770 (2)	0.4718 (5)	0.35037 (10)	0.0629 (8)
H4A	0.6974	0.5352	0.3756	0.075*
C5A	0.6471 (2)	0.2668 (5)	0.35018 (9)	0.0607 (8)
C6A	0.6160 (2)	0.1754 (5)	0.31277 (8)	0.0564 (7)
H6A	0.5944	0.0385	0.3128	0.068*
C7A	0.6930 (4)	0.2192 (8)	0.42341 (11)	0.1045 (14)
H7A1	0.6875	0.1179	0.4454	0.157*
H7A2	0.6605	0.3448	0.4314	0.157*
H7A3	0.7618	0.2469	0.4192	0.157*
C8A	0.59249 (19)	0.1754 (5)	0.23556 (8)	0.0517 (7)
H8A	0.5768	0.0352	0.2365	0.062*
C9A	0.5837 (2)	0.1543 (4)	0.16155 (8)	0.0502 (6)
C10A	0.6170 (2)	−0.0492 (5)	0.15797 (9)	0.0561 (7)
H10A	0.6420	−0.1193	0.1818	0.067*
C11A	0.6127 (2)	−0.1466 (5)	0.11934 (10)	0.0631 (8)
H11A	0.6342	−0.2831	0.1174	0.076*
C12A	0.5771 (2)	−0.0451 (5)	0.08346 (10)	0.0636 (8)
H12A	0.5743	−0.1118	0.0574	0.076*
C13A	0.5455 (2)	0.1581 (5)	0.08704 (9)	0.0596 (7)
C14A	0.5483 (2)	0.2566 (5)	0.12565 (9)	0.0567 (7)
H14A	0.5263	0.3927	0.1276	0.068*
C15A	0.5104 (3)	0.2720 (5)	0.04844 (10)	0.0829 (11)
N1A	0.59247 (17)	0.2674 (4)	0.19956 (7)	0.0529 (6)
O1A	0.64877 (18)	0.6071 (4)	0.23935 (7)	0.0691 (6)
O2A	0.6472 (2)	0.1424 (4)	0.38544 (7)	0.0873 (8)
C1	0.10504 (19)	0.2748 (5)	0.24086 (9)	0.0527 (7)
C2	0.1374 (2)	0.4839 (5)	0.23806 (9)	0.0564 (7)
C3	0.1381 (2)	0.5767 (5)	0.19883 (11)	0.0649 (8)
H3	0.1589	0.7136	0.1968	0.078*
C4	0.1089 (2)	0.4713 (6)	0.16290 (11)	0.0692 (9)
H4	0.1098	0.5373	0.1369	0.083*
C5	0.0776 (2)	0.2655 (6)	0.16503 (10)	0.0642 (8)
C6	0.0749 (2)	0.1719 (5)	0.20390 (9)	0.0584 (7)
H6	0.0523	0.0361	0.2055	0.070*
C7	0.0736 (3)	0.2186 (9)	0.09038 (11)	0.1054 (15)
H7A	0.0501	0.1211	0.0694	0.158*
H7B	0.1443	0.2333	0.0892	0.158*
H7C	0.0424	0.3505	0.0852	0.158*
C8	0.1080 (2)	0.1653 (5)	0.28078 (9)	0.0549 (7)
H8	0.0905	0.0258	0.2812	0.066*
C9	0.1463 (2)	0.1420 (5)	0.35335 (9)	0.0559 (7)
C10	0.1841 (2)	−0.0589 (5)	0.35468 (10)	0.0620 (8)
H10	0.1978	−0.1267	0.3297	0.074*
C11	0.2011 (3)	−0.1575 (6)	0.39286 (11)	0.0741 (9)
H11	0.2256	−0.2922	0.3935	0.089*
C12	0.1821 (3)	−0.0587 (6)	0.42978 (11)	0.0795 (10)
H12	0.1941	−0.1258	0.4555	0.095*
C13	0.1451 (3)	0.1413 (6)	0.42881 (10)	0.0749 (9)
C14	0.1274 (2)	0.2419 (5)	0.39071 (9)	0.0655 (8)
H14	0.1028	0.3766	0.3902	0.079*
C15	0.1269 (5)	0.2510 (8)	0.46891 (13)	0.1131 (16)
N1	0.13402 (17)	0.2560 (4)	0.31550 (7)	0.0555 (6)
O1	0.16842 (17)	0.5928 (4)	0.27249 (8)	0.0710 (6)
O2	0.0501 (2)	0.1466 (5)	0.13076 (7)	0.0893 (8)
F4A	0.5051 (12)	0.4750 (10)	0.0524 (3)	0.089 (2)	0.62 (3)
F5A	0.5747 (12)	0.2314 (18)	0.0164 (3)	0.109 (3)	0.62 (3)
F6A	0.4221 (8)	0.220 (2)	0.0334 (4)	0.126 (3)	0.62 (3)
F4B	0.5467 (18)	0.466 (2)	0.0490 (6)	0.094 (4)	0.38 (3)
F5B	0.5269 (19)	0.191 (2)	0.0124 (3)	0.104 (4)	0.38 (3)
F6B	0.4096 (8)	0.275 (4)	0.0467 (8)	0.137 (6)	0.38 (3)
H1	0.162 (3)	0.506 (7)	0.2948 (13)	0.095 (14)*
H1A	0.627 (3)	0.535 (7)	0.2175 (13)	0.091 (13)*

	U11	U22	U33	U12	U13	U23
F1A	0.211 (8)	0.094 (4)	0.074 (3)	0.016 (4)	0.022 (4)	−0.028 (2)
F2A	0.204 (8)	0.175 (7)	0.083 (4)	0.046 (6)	−0.034 (4)	−0.028 (4)
F3A	0.230 (8)	0.181 (8)	0.159 (7)	−0.003 (6)	0.113 (6)	−0.048 (6)
F1B	0.216 (10)	0.161 (9)	0.120 (6)	−0.031 (8)	0.029 (7)	−0.066 (6)
F2B	0.189 (9)	0.140 (7)	0.051 (4)	0.014 (6)	0.029 (5)	0.005 (4)
F3B	0.219 (10)	0.174 (11)	0.154 (8)	0.067 (8)	0.059 (7)	−0.026 (8)
C1A	0.0495 (14)	0.0506 (16)	0.0478 (14)	0.0021 (12)	0.0037 (11)	0.0036 (12)
C2A	0.0495 (14)	0.0529 (17)	0.0542 (16)	0.0006 (12)	0.0020 (11)	0.0071 (13)
C3A	0.0552 (16)	0.0545 (18)	0.0692 (19)	−0.0009 (13)	0.0029 (13)	−0.0075 (14)
C4A	0.0592 (17)	0.076 (2)	0.0533 (16)	−0.0008 (15)	−0.0001 (13)	−0.0100 (15)
C5A	0.0610 (17)	0.072 (2)	0.0489 (15)	0.0024 (15)	0.0060 (12)	0.0053 (14)
C6A	0.0654 (17)	0.0543 (17)	0.0500 (15)	−0.0006 (14)	0.0063 (12)	0.0068 (13)
C7A	0.131 (4)	0.130 (4)	0.052 (2)	0.001 (3)	−0.009 (2)	0.008 (2)
C8A	0.0520 (15)	0.0523 (17)	0.0507 (15)	−0.0048 (12)	0.0012 (11)	0.0065 (12)
C9A	0.0506 (14)	0.0516 (16)	0.0480 (14)	−0.0060 (12)	−0.0010 (11)	0.0061 (12)
C10A	0.0616 (17)	0.0522 (17)	0.0539 (16)	0.0013 (13)	−0.0029 (12)	0.0081 (13)
C11A	0.076 (2)	0.0478 (17)	0.0650 (18)	0.0028 (15)	−0.0039 (14)	0.0017 (14)
C12A	0.081 (2)	0.0553 (19)	0.0534 (16)	−0.0049 (16)	−0.0049 (14)	−0.0045 (14)
C13A	0.079 (2)	0.0516 (18)	0.0479 (15)	0.0000 (15)	−0.0057 (13)	0.0042 (13)
C14A	0.0707 (18)	0.0469 (17)	0.0521 (15)	0.0007 (14)	−0.0017 (13)	0.0047 (12)
C15A	0.132 (4)	0.060 (2)	0.0557 (19)	0.008 (2)	−0.015 (2)	−0.0002 (16)
N1A	0.0560 (13)	0.0553 (14)	0.0470 (12)	−0.0017 (11)	−0.0007 (10)	0.0053 (10)
O1A	0.0904 (16)	0.0550 (14)	0.0612 (13)	−0.0100 (11)	−0.0048 (11)	0.0140 (11)
O2A	0.117 (2)	0.098 (2)	0.0461 (12)	−0.0097 (15)	−0.0007 (12)	0.0132 (12)
C1	0.0472 (14)	0.0555 (18)	0.0560 (16)	−0.0006 (12)	0.0074 (11)	−0.0035 (13)
C2	0.0504 (15)	0.0551 (18)	0.0643 (18)	−0.0013 (13)	0.0082 (12)	−0.0015 (14)
C3	0.0597 (17)	0.0587 (19)	0.077 (2)	−0.0005 (14)	0.0098 (15)	0.0070 (16)
C4	0.0597 (18)	0.080 (2)	0.0683 (19)	0.0061 (16)	0.0077 (14)	0.0163 (18)
C5	0.0538 (16)	0.080 (2)	0.0587 (17)	−0.0008 (16)	0.0008 (13)	−0.0015 (16)
C6	0.0547 (16)	0.0586 (18)	0.0622 (17)	−0.0046 (13)	0.0052 (13)	0.0003 (14)
C7	0.110 (3)	0.150 (4)	0.057 (2)	−0.004 (3)	0.002 (2)	0.000 (2)
C8	0.0522 (15)	0.0533 (17)	0.0596 (17)	−0.0017 (13)	0.0062 (12)	−0.0023 (13)
C9	0.0528 (15)	0.0599 (19)	0.0553 (16)	−0.0041 (14)	0.0065 (12)	−0.0040 (14)
C10	0.0619 (17)	0.0594 (19)	0.0648 (18)	0.0021 (14)	0.0035 (14)	−0.0109 (15)
C11	0.079 (2)	0.063 (2)	0.081 (2)	0.0049 (17)	0.0050 (17)	0.0017 (18)
C12	0.096 (3)	0.075 (2)	0.067 (2)	0.004 (2)	0.0064 (18)	0.0115 (18)
C13	0.093 (2)	0.076 (2)	0.0571 (18)	0.0038 (19)	0.0165 (16)	−0.0019 (16)
C14	0.078 (2)	0.0609 (19)	0.0581 (17)	0.0026 (16)	0.0119 (14)	−0.0062 (14)
C15	0.169 (5)	0.110 (4)	0.062 (2)	0.017 (4)	0.020 (3)	0.005 (2)
N1	0.0572 (13)	0.0584 (15)	0.0511 (13)	−0.0012 (11)	0.0063 (10)	−0.0062 (11)
O1	0.0809 (15)	0.0589 (14)	0.0735 (15)	−0.0107 (11)	0.0076 (12)	−0.0116 (12)
O2	0.1061 (19)	0.109 (2)	0.0523 (13)	−0.0176 (16)	−0.0021 (12)	−0.0022 (13)
F4A	0.143 (6)	0.060 (3)	0.063 (3)	0.019 (3)	−0.010 (4)	0.0089 (19)
F5A	0.159 (7)	0.117 (5)	0.052 (3)	0.019 (4)	0.010 (3)	0.020 (3)
F6A	0.149 (6)	0.120 (6)	0.102 (5)	−0.017 (4)	−0.072 (4)	0.019 (4)
F4B	0.137 (9)	0.065 (5)	0.077 (5)	−0.011 (5)	−0.020 (7)	0.023 (4)
F5B	0.158 (10)	0.091 (6)	0.059 (4)	0.013 (6)	−0.028 (5)	−0.012 (4)
F6B	0.151 (8)	0.134 (10)	0.118 (10)	0.021 (6)	−0.064 (6)	0.019 (7)

F1A—C15	1.290 (6)	C15A—F6A	1.306 (7)
F2A—C15	1.352 (7)	C15A—F4A	1.318 (7)
F3A—C15	1.362 (9)	C15A—F4B	1.345 (9)
F1B—C15	1.376 (9)	C15A—F6B	1.358 (10)
F2B—C15	1.295 (7)	C15A—F5A	1.389 (7)
F3B—C15	1.323 (10)	O1A—H1A	0.87 (4)
C1A—C6A	1.395 (4)	C1—C6	1.391 (4)
C1A—C2A	1.415 (4)	C1—C2	1.422 (4)
C1A—C8A	1.448 (4)	C1—C8	1.449 (4)
C2A—O1A	1.356 (3)	C2—O1	1.348 (4)
C2A—C3A	1.372 (4)	C2—C3	1.381 (4)
C3A—C4A	1.379 (4)	C3—C4	1.369 (5)
C3A—H3A	0.9300	C3—H3	0.9300
C4A—C5A	1.383 (5)	C4—C5	1.396 (5)
C4A—H4A	0.9300	C4—H4	0.9300
C5A—C6A	1.373 (4)	C5—O2	1.367 (4)
C5A—O2A	1.377 (4)	C5—C6	1.375 (4)
C6A—H6A	0.9300	C6—H6	0.9300
C7A—O2A	1.417 (4)	C7—O2	1.412 (4)
C7A—H7A1	0.9600	C7—H7A	0.9600
C7A—H7A2	0.9600	C7—H7B	0.9600
C7A—H7A3	0.9600	C7—H7C	0.9600
C8A—N1A	1.287 (3)	C8—N1	1.282 (4)
C8A—H8A	0.9300	C8—H8	0.9300
C9A—C14A	1.382 (4)	C9—C14	1.383 (4)
C9A—C10A	1.393 (4)	C9—C10	1.393 (4)
C9A—N1A	1.410 (3)	C9—N1	1.411 (4)
C10A—C11A	1.376 (4)	C10—C11	1.377 (5)
C10A—H10A	0.9300	C10—H10	0.9300
C11A—C12A	1.380 (4)	C11—C12	1.367 (5)
C11A—H11A	0.9300	C11—H11	0.9300
C12A—C13A	1.385 (4)	C12—C13	1.383 (5)
C12A—H12A	0.9300	C12—H12	0.9300
C13A—C14A	1.378 (4)	C13—C14	1.383 (5)
C13A—C15A	1.486 (4)	C13—C15	1.486 (6)
C14A—H14A	0.9300	C14—H14	0.9300
C15A—F5B	1.285 (9)	O1—H1	0.91 (4)
C6A—C1A—C2A	118.7 (3)	C6—C1—C8	119.9 (3)
C6A—C1A—C8A	119.3 (3)	C2—C1—C8	121.4 (3)
C2A—C1A—C8A	121.8 (2)	O1—C2—C3	119.2 (3)
O1A—C2A—C3A	119.6 (3)	O1—C2—C1	121.9 (3)
O1A—C2A—C1A	121.4 (3)	C3—C2—C1	118.8 (3)
C3A—C2A—C1A	119.0 (3)	C4—C3—C2	121.4 (3)
C2A—C3A—C4A	121.4 (3)	C4—C3—H3	119.3
C2A—C3A—H3A	119.3	C2—C3—H3	119.3
C4A—C3A—H3A	119.3	C3—C4—C5	120.5 (3)
C3A—C4A—C5A	120.1 (3)	C3—C4—H4	119.7
C3A—C4A—H4A	119.9	C5—C4—H4	119.7
C5A—C4A—H4A	119.9	O2—C5—C6	116.7 (3)
C6A—C5A—O2A	116.1 (3)	O2—C5—C4	124.5 (3)
C6A—C5A—C4A	119.5 (3)	C6—C5—C4	118.8 (3)
O2A—C5A—C4A	124.4 (3)	C5—C6—C1	121.8 (3)
C5A—C6A—C1A	121.3 (3)	C5—C6—H6	119.1
C5A—C6A—H6A	119.4	C1—C6—H6	119.1
C1A—C6A—H6A	119.4	O2—C7—H7A	109.5
O2A—C7A—H7A1	109.5	O2—C7—H7B	109.5
O2A—C7A—H7A2	109.5	H7A—C7—H7B	109.5
H7A1—C7A—H7A2	109.5	O2—C7—H7C	109.5
O2A—C7A—H7A3	109.5	H7A—C7—H7C	109.5
H7A1—C7A—H7A3	109.5	H7B—C7—H7C	109.5
H7A2—C7A—H7A3	109.5	N1—C8—C1	121.5 (3)
N1A—C8A—C1A	121.9 (3)	N1—C8—H8	119.2
N1A—C8A—H8A	119.1	C1—C8—H8	119.2
C1A—C8A—H8A	119.1	C14—C9—C10	119.3 (3)
C14A—C9A—C10A	118.9 (3)	C14—C9—N1	117.8 (3)
C14A—C9A—N1A	118.0 (3)	C10—C9—N1	122.7 (3)
C10A—C9A—N1A	122.9 (2)	C11—C10—C9	120.1 (3)
C11A—C10A—C9A	120.2 (3)	C11—C10—H10	119.9
C11A—C10A—H10A	119.9	C9—C10—H10	119.9
C9A—C10A—H10A	119.9	C12—C11—C10	120.5 (3)
C10A—C11A—C12A	121.1 (3)	C12—C11—H11	119.8
C10A—C11A—H11A	119.5	C10—C11—H11	119.8
C12A—C11A—H11A	119.5	C11—C12—C13	119.8 (3)
C11A—C12A—C13A	118.6 (3)	C11—C12—H12	120.1
C11A—C12A—H12A	120.7	C13—C12—H12	120.1
C13A—C12A—H12A	120.7	C14—C13—C12	120.3 (3)
C14A—C13A—C12A	120.9 (3)	C14—C13—C15	119.7 (4)
C14A—C13A—C15A	119.9 (3)	C12—C13—C15	119.9 (3)
C12A—C13A—C15A	119.2 (3)	C13—C14—C9	119.9 (3)
C13A—C14A—C9A	120.4 (3)	C13—C14—H14	120.0
C13A—C14A—H14A	119.8	C9—C14—H14	120.0
C9A—C14A—H14A	119.8	F1A—C15—F2B	130.2 (6)
F5B—C15A—F6A	76.3 (8)	F1A—C15—F3B	66.3 (8)
F5B—C15A—F4A	120.2 (8)	F2B—C15—F3B	94.1 (11)
F6A—C15A—F4A	103.8 (7)	F1A—C15—F2A	110.6 (6)
F5B—C15A—F4B	108.3 (10)	F3B—C15—F2A	124.9 (10)
F6A—C15A—F4B	124.8 (9)	F1A—C15—F3A	96.5 (8)
F5B—C15A—F6B	100.6 (9)	F2B—C15—F3A	68.9 (8)
F4A—C15A—F6B	86.0 (9)	F2A—C15—F3A	109.4 (8)
F4B—C15A—F6B	110.4 (11)	F1A—C15—F1B	47.0 (7)
F6A—C15A—F5A	105.9 (6)	F2B—C15—F1B	113.6 (8)
F4A—C15A—F5A	107.2 (6)	F3B—C15—F1B	111.0 (11)
F4B—C15A—F5A	87.0 (9)	F2A—C15—F1B	73.5 (8)
F6B—C15A—F5A	129.1 (8)	F3A—C15—F1B	136.9 (9)
F5B—C15A—C13A	118.0 (7)	F1A—C15—C13	116.7 (4)
F6A—C15A—C13A	115.0 (6)	F2B—C15—C13	113.1 (6)
F4A—C15A—C13A	115.4 (5)	F3B—C15—C13	115.3 (10)
F4B—C15A—C13A	110.4 (8)	F2A—C15—C13	113.9 (5)
F6B—C15A—C13A	108.6 (9)	F3A—C15—C13	108.2 (6)
F5A—C15A—C13A	108.9 (5)	F1B—C15—C13	109.3 (6)
C8A—N1A—C9A	121.1 (3)	C8—N1—C9	120.6 (3)
C2A—O1A—H1A	111 (3)	C2—O1—H1	106 (3)
C5A—O2A—C7A	118.1 (3)	C5—O2—C7	118.2 (3)
C6—C1—C2	118.6 (3)
C6A—C1A—C2A—O1A	−180.0 (3)	C6—C1—C2—O1	−179.4 (3)
C8A—C1A—C2A—O1A	4.9 (4)	C8—C1—C2—O1	−2.7 (4)
C6A—C1A—C2A—C3A	0.8 (4)	C6—C1—C2—C3	−0.3 (4)
C8A—C1A—C2A—C3A	−174.3 (3)	C8—C1—C2—C3	176.4 (3)
O1A—C2A—C3A—C4A	−179.4 (3)	O1—C2—C3—C4	178.9 (3)
C1A—C2A—C3A—C4A	−0.1 (4)	C1—C2—C3—C4	−0.3 (4)
C2A—C3A—C4A—C5A	0.1 (5)	C2—C3—C4—C5	−0.2 (5)
C3A—C4A—C5A—C6A	−0.8 (4)	C3—C4—C5—O2	−177.9 (3)
C3A—C4A—C5A—O2A	178.2 (3)	C3—C4—C5—C6	1.2 (5)
O2A—C5A—C6A—C1A	−177.6 (3)	O2—C5—C6—C1	177.3 (3)
C4A—C5A—C6A—C1A	1.5 (5)	C4—C5—C6—C1	−1.8 (4)
C2A—C1A—C6A—C5A	−1.5 (4)	C2—C1—C6—C5	1.4 (4)
C8A—C1A—C6A—C5A	173.8 (3)	C8—C1—C6—C5	−175.4 (3)
C6A—C1A—C8A—N1A	−179.4 (3)	C6—C1—C8—N1	−179.0 (3)
C2A—C1A—C8A—N1A	−4.3 (4)	C2—C1—C8—N1	4.3 (4)
C14A—C9A—C10A—C11A	−1.1 (4)	C14—C9—C10—C11	0.8 (4)
N1A—C9A—C10A—C11A	−175.4 (3)	N1—C9—C10—C11	175.4 (3)
C9A—C10A—C11A—C12A	0.9 (5)	C9—C10—C11—C12	−0.7 (5)
C10A—C11A—C12A—C13A	0.1 (5)	C10—C11—C12—C13	0.3 (6)
C11A—C12A—C13A—C14A	−0.8 (5)	C11—C12—C13—C14	−0.1 (6)
C11A—C12A—C13A—C15A	177.8 (3)	C11—C12—C13—C15	−178.4 (4)
C12A—C13A—C14A—C9A	0.6 (5)	C12—C13—C14—C9	0.3 (5)
C15A—C13A—C14A—C9A	−178.0 (3)	C15—C13—C14—C9	178.5 (4)
C10A—C9A—C14A—C13A	0.4 (4)	C10—C9—C14—C13	−0.6 (5)
N1A—C9A—C14A—C13A	174.9 (3)	N1—C9—C14—C13	−175.5 (3)
C14A—C13A—C15A—F5B	166.6 (13)	C14—C13—C15—F1A	−18.4 (9)
C12A—C13A—C15A—F5B	−12.0 (14)	C12—C13—C15—F1A	159.9 (8)
C14A—C13A—C15A—F6A	−106.2 (9)	C14—C13—C15—F2B	163.3 (10)
C12A—C13A—C15A—F6A	75.2 (9)	C12—C13—C15—F2B	−18.5 (11)
C14A—C13A—C15A—F4A	14.6 (10)	C14—C13—C15—F3B	56.6 (12)
C12A—C13A—C15A—F4A	−164.0 (9)	C12—C13—C15—F3B	−125.1 (12)
C14A—C13A—C15A—F4B	41.4 (14)	C14—C13—C15—F2A	−149.1 (9)
C12A—C13A—C15A—F4B	−137.3 (13)	C12—C13—C15—F2A	29.1 (10)
C14A—C13A—C15A—F6B	−79.9 (13)	C14—C13—C15—F3A	89.0 (9)
C12A—C13A—C15A—F6B	101.5 (12)	C12—C13—C15—F3A	−92.7 (9)
C14A—C13A—C15A—F5A	135.2 (8)	C14—C13—C15—F1B	−69.1 (11)
C12A—C13A—C15A—F5A	−43.4 (9)	C12—C13—C15—F1B	109.1 (11)
C1A—C8A—N1A—C9A	170.5 (2)	C1—C8—N1—C9	−173.4 (2)
C14A—C9A—N1A—C8A	156.8 (3)	C14—C9—N1—C8	−149.7 (3)
C10A—C9A—N1A—C8A	−28.8 (4)	C10—C9—N1—C8	35.6 (4)
C6A—C5A—O2A—C7A	170.3 (3)	C6—C5—O2—C7	−165.4 (3)
C4A—C5A—O2A—C7A	−8.7 (5)	C4—C5—O2—C7	13.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.91 (4)	1.79 (4)	2.619 (4)	150 (4)
O1A—H1A···N1A	0.87 (4)	1.87 (4)	2.623 (3)	143 (4)
C10—H10···O1i	0.93	2.58	3.444 (3)	154
C10A—H10A···O1Ai	0.93	2.54	3.413 (3)	157
C3—H3···Cg3ii	0.93	2.86	3.526 (3)	130
C3A—H3A···Cg1ii	0.93	2.88	3.518 (3)	127
C11—H11···Cg4iii	0.93	2.85	3.529 (3)	131
C11A—H11A···Cg2iii	0.93	2.97	3.646 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.91 (4)	1.79 (4)	2.619 (4)	150 (4)
O1A—H1A⋯N1A	0.87 (4)	1.87 (4)	2.623 (3)	143 (4)
C10—H10⋯O1i	0.93	2.58	3.444 (3)	154
C10A—H10A⋯O1A i	0.93	2.54	3.413 (3)	157
C3—H3⋯Cg3ii	0.93	2.86	3.526 (3)	130
C3A—H3A⋯Cg1ii	0.93	2.88	3.518 (3)	127
C11—H11⋯Cg4iii	0.93	2.85	3.529 (3)	131
C11A—H11A⋯Cg2iii	0.93	2.97	3.646 (3)	131

Symmetry codes: (i) ; (ii) ; (iii) . Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1–C6, C9-C14, C1A–C6A and C9A–C14A rings, respectively.