2-[N-(2,4-Difluoro-phen-yl)carbamo-yl]-3,4,5,6-tetra-fluoro-benzoic acid.

The title compound, C(14)H(5)F(6)NO(3), was synthesized by condensation of tetra-fluoro-phthalic anhydride and 2,4-difluoro-aniline. It was then recrystallized from hexane to give a nonmerohedral twin with two crystallographically unique mol-ecules in the asymmetric unit. The refined twin fraction is 0.460 (3). Torsional differences between the aryl rings and the central amide group account for the presence of two unique mol-ecules. The compound packs as double tapes formed by O-H⋯O and N-H⋯O hydrogen-bonding inter-actions between each unique mol-ecule and its symmetry equivalents.

Related literature

For the synthesis of a related structure, see: Collin et al. (2001 ▶). For anti­tumor effects of thalidomide analogs, see: Ng et al. (2004 ▶).

Experimental

Crystal data

C14H5F6NO3

M = 349.19

Triclinic,

a = 7.5293 (4) Å

b = 7.6795 (5) Å

c = 24.1969 (15) Å

α = 89.809 (5)°

β = 82.747 (4)°

γ = 68.712 (4)°

V = 1291.83 (13) Å3

Z = 4

Cu Kα radiation

μ = 1.65 mm−1

T = 100 K

0.27 × 0.19 × 0.09 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer

Absorption correction: multi-scan (TWINABS; Sheldrick, 1996 ▶) T min = 0.664, T max = 0.868

7781 measured reflections

3296 independent reflections

2467 reflections with I > 2σ(I)

R int = 0.074

θmax = 58.5°

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.182

S = 0.99

3296 reflections

434 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038306/bt5063sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038306/bt5063Isup2.hkl

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

C14H5F6NO3	Z = 4
Mr = 349.19	F(000) = 696
Triclinic, P1	Dx = 1.795 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 7.5293 (4) Å	Cell parameters from 617 reflections
b = 7.6795 (5) Å	θ = 3.7–56.9°
c = 24.1969 (15) Å	µ = 1.65 mm−1
α = 89.809 (5)°	T = 100 K
β = 82.747 (4)°	Prism, colorless
γ = 68.712 (4)°	0.27 × 0.19 × 0.09 mm
V = 1291.83 (13) Å3

Bruker Kappa APEXII DUO CCD diffractometer	3296 independent reflections
Radiation source: microsource	2467 reflections with I > 2σ(I)
silicon	Rint = 0.074
φ and ω scans	θmax = 58.5°, θmin = 1.8°
Absorption correction: multi-scan (TWINABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.664, Tmax = 0.868	k = −8→8
7781 measured reflections	l = 0→26

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.1222P)2] where P = (Fo2 + 2Fc2)/3
3296 reflections	(Δ/σ)max < 0.001
434 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

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
F1	0.6312 (6)	0.7940 (5)	0.07802 (17)	0.0314 (10)
F2	0.5202 (6)	0.7903 (6)	0.18695 (17)	0.0342 (11)
F3	0.5293 (7)	0.4660 (6)	0.23442 (17)	0.0380 (12)
F4	0.6469 (7)	0.1469 (6)	0.17134 (17)	0.0368 (11)
F5	0.8026 (6)	0.3185 (6)	−0.11126 (18)	0.0310 (10)
F6	0.9832 (7)	0.7035 (7)	−0.23925 (18)	0.0441 (13)
O1	0.9457 (6)	0.3317 (6)	−0.0108 (2)	0.0233 (11)
O2	0.6865 (7)	0.1123 (7)	0.01592 (19)	0.0252 (12)
O3	0.9119 (7)	−0.0116 (6)	0.0722 (2)	0.0279 (12)
H3	0.9411	−0.1078	0.0513	0.034*
N1	0.6934 (8)	0.5969 (8)	−0.0258 (2)	0.0208 (13)
H1	0.5782	0.6737	−0.0115	0.025*
C1	0.7927 (10)	0.4594 (10)	0.0057 (3)	0.0221 (17)
C2	0.7033 (10)	0.4683 (10)	0.0659 (3)	0.0233 (17)
C3	0.6390 (10)	0.6307 (10)	0.0997 (3)	0.0252 (17)
C4	0.5817 (10)	0.6302 (10)	0.1557 (3)	0.0257 (17)
C5	0.5853 (11)	0.4681 (11)	0.1803 (3)	0.0270 (18)
C6	0.6523 (11)	0.3034 (10)	0.1465 (3)	0.0289 (19)
C7	0.7083 (10)	0.3010 (10)	0.0908 (3)	0.0210 (16)
C8	0.7685 (10)	0.1238 (10)	0.0551 (3)	0.0229 (16)
C9	0.7661 (10)	0.6233 (10)	−0.0807 (3)	0.0216 (16)
C10	0.8250 (11)	0.4836 (10)	−0.1232 (3)	0.0285 (18)
C11	0.8983 (11)	0.5061 (10)	−0.1755 (3)	0.0288 (18)
H11	0.9396	0.4074	−0.2032	0.035*
C12	0.9107 (11)	0.6748 (12)	−0.1869 (3)	0.032 (2)
C13	0.8517 (11)	0.8235 (11)	−0.1472 (3)	0.0289 (18)
H13	0.8582	0.9414	−0.1566	0.035*
C14	0.7839 (11)	0.7933 (11)	−0.0938 (3)	0.0285 (18)
H14	0.7487	0.8899	−0.0655	0.034*
F51	0.7042 (6)	0.2634 (6)	0.41888 (17)	0.0305 (10)
F52	0.6881 (7)	0.2199 (6)	0.31022 (18)	0.0402 (12)
F53	0.7306 (6)	−0.1187 (6)	0.26531 (18)	0.0383 (11)
F54	0.7893 (7)	−0.4145 (6)	0.33004 (18)	0.0350 (11)
F55	0.6962 (6)	−0.1608 (5)	0.60603 (17)	0.0311 (11)
F56	0.8200 (6)	0.2169 (6)	0.73646 (18)	0.0413 (12)
O51	0.9354 (7)	−0.1677 (7)	0.5081 (2)	0.0264 (12)
O52	0.6925 (7)	−0.3957 (7)	0.4849 (2)	0.0259 (12)
O53	0.9737 (7)	−0.5342 (6)	0.4286 (2)	0.0279 (12)
H53	0.9875	−0.6255	0.4491	0.034*
N51	0.6738 (9)	0.1005 (8)	0.5249 (2)	0.0251 (14)
H51	0.5713	0.1778	0.5119	0.030*
C51	0.7952 (11)	−0.0447 (10)	0.4919 (3)	0.0245 (17)
C52	0.7609 (10)	−0.0563 (10)	0.4324 (3)	0.0253 (17)
C53	0.7284 (11)	0.0938 (10)	0.3988 (3)	0.0269 (17)
C54	0.7213 (11)	0.0727 (10)	0.3424 (3)	0.0270 (18)
C55	0.7409 (11)	−0.1006 (11)	0.3196 (3)	0.0268 (18)
C56	0.7748 (10)	−0.2496 (10)	0.3531 (3)	0.0236 (17)
C57	0.7811 (10)	−0.2303 (10)	0.4091 (3)	0.0221 (17)
C58	0.8084 (11)	−0.3979 (10)	0.4460 (3)	0.0246 (17)
C59	0.7037 (11)	0.1344 (10)	0.5794 (3)	0.0272 (18)
C60	0.7205 (10)	0.0006 (10)	0.6193 (3)	0.0252 (17)
C61	0.7593 (11)	0.0240 (11)	0.6723 (3)	0.0307 (18)
H61	0.7755	−0.0707	0.6986	0.037*
C62	0.7733 (12)	0.1938 (11)	0.6849 (3)	0.032 (2)
C63	0.7495 (11)	0.3315 (11)	0.6487 (3)	0.0299 (19)
H63	0.7575	0.4470	0.6595	0.036*
C64	0.7138 (11)	0.3034 (11)	0.5961 (3)	0.0300 (18)
H64	0.6955	0.4007	0.5706	0.036*

	U11	U22	U33	U12	U13	U23
F1	0.040 (3)	0.024 (2)	0.032 (2)	−0.014 (2)	−0.003 (2)	−0.0027 (19)
F2	0.040 (3)	0.029 (2)	0.032 (2)	−0.010 (2)	−0.005 (2)	−0.006 (2)
F3	0.047 (3)	0.033 (3)	0.022 (2)	−0.002 (2)	−0.001 (2)	0.0010 (19)
F4	0.052 (3)	0.021 (2)	0.032 (2)	−0.008 (2)	−0.002 (2)	0.0045 (19)
F5	0.029 (2)	0.027 (2)	0.038 (3)	−0.010 (2)	−0.013 (2)	0.0016 (19)
F6	0.052 (3)	0.051 (3)	0.023 (2)	−0.016 (2)	0.006 (2)	0.007 (2)
O1	0.015 (3)	0.018 (3)	0.034 (3)	−0.002 (2)	−0.005 (2)	−0.006 (2)
O2	0.024 (3)	0.027 (3)	0.028 (3)	−0.013 (2)	−0.003 (2)	−0.003 (2)
O3	0.035 (3)	0.014 (3)	0.033 (3)	−0.004 (2)	−0.015 (2)	−0.001 (2)
N1	0.005 (3)	0.024 (3)	0.031 (3)	−0.001 (2)	−0.009 (3)	0.005 (3)
C1	0.027 (4)	0.019 (4)	0.030 (4)	−0.016 (4)	−0.011 (3)	−0.001 (3)
C2	0.019 (4)	0.033 (4)	0.029 (4)	−0.020 (3)	−0.009 (3)	0.001 (3)
C3	0.016 (4)	0.018 (4)	0.038 (4)	−0.003 (3)	−0.005 (4)	0.001 (3)
C4	0.027 (4)	0.029 (4)	0.025 (4)	−0.013 (3)	−0.007 (3)	−0.007 (3)
C5	0.024 (4)	0.025 (4)	0.029 (4)	−0.004 (3)	−0.009 (3)	0.000 (3)
C6	0.030 (4)	0.022 (4)	0.036 (5)	−0.009 (4)	−0.009 (4)	0.015 (4)
C7	0.016 (4)	0.024 (4)	0.024 (4)	−0.008 (3)	−0.006 (3)	0.004 (3)
C8	0.023 (4)	0.028 (4)	0.021 (4)	−0.014 (3)	−0.001 (3)	0.002 (3)
C9	0.015 (4)	0.026 (4)	0.022 (4)	−0.004 (3)	−0.008 (3)	0.002 (3)
C10	0.031 (4)	0.026 (4)	0.031 (4)	−0.012 (4)	−0.005 (4)	0.005 (3)
C11	0.031 (4)	0.018 (4)	0.031 (4)	−0.002 (3)	−0.004 (4)	−0.005 (3)
C12	0.024 (4)	0.044 (5)	0.025 (4)	−0.009 (4)	−0.003 (3)	0.003 (4)
C13	0.027 (4)	0.024 (4)	0.038 (5)	−0.009 (3)	−0.011 (4)	0.012 (4)
C14	0.032 (4)	0.032 (4)	0.028 (4)	−0.015 (4)	−0.014 (3)	0.006 (4)
F51	0.035 (2)	0.022 (2)	0.036 (2)	−0.0108 (19)	−0.010 (2)	0.0055 (19)
F52	0.052 (3)	0.035 (3)	0.034 (3)	−0.015 (2)	−0.011 (2)	0.013 (2)
F53	0.047 (3)	0.042 (3)	0.027 (2)	−0.017 (2)	−0.007 (2)	0.005 (2)
F54	0.042 (3)	0.026 (2)	0.035 (3)	−0.007 (2)	−0.011 (2)	−0.005 (2)
F55	0.036 (2)	0.018 (2)	0.039 (3)	−0.010 (2)	0.000 (2)	0.0043 (19)
F56	0.036 (3)	0.051 (3)	0.036 (3)	−0.015 (2)	−0.007 (2)	−0.008 (2)
O51	0.031 (3)	0.019 (3)	0.031 (3)	−0.011 (3)	−0.006 (2)	0.001 (2)
O52	0.024 (3)	0.021 (3)	0.033 (3)	−0.008 (2)	−0.001 (3)	0.005 (2)
O53	0.023 (3)	0.020 (3)	0.041 (3)	−0.008 (2)	−0.004 (2)	0.009 (2)
N51	0.024 (3)	0.022 (3)	0.027 (3)	−0.005 (3)	−0.009 (3)	0.002 (3)
C51	0.029 (4)	0.024 (4)	0.028 (4)	−0.016 (4)	−0.009 (4)	0.010 (3)
C52	0.019 (4)	0.026 (4)	0.030 (4)	−0.006 (3)	−0.005 (3)	−0.002 (3)
C53	0.021 (4)	0.024 (4)	0.036 (5)	−0.008 (3)	−0.005 (4)	0.005 (4)
C54	0.022 (4)	0.024 (4)	0.033 (4)	−0.007 (3)	−0.005 (3)	0.018 (4)
C55	0.018 (4)	0.033 (5)	0.025 (4)	−0.002 (3)	−0.006 (3)	0.003 (4)
C56	0.018 (4)	0.026 (4)	0.032 (4)	−0.013 (3)	−0.007 (3)	−0.001 (4)
C57	0.014 (4)	0.022 (4)	0.028 (4)	−0.005 (3)	−0.003 (3)	0.006 (3)
C58	0.021 (4)	0.014 (4)	0.038 (5)	−0.003 (3)	−0.011 (4)	−0.001 (3)
C59	0.024 (4)	0.027 (4)	0.026 (4)	−0.004 (3)	−0.003 (3)	0.008 (3)
C60	0.015 (4)	0.018 (4)	0.041 (5)	−0.004 (3)	−0.005 (3)	−0.001 (3)
C61	0.031 (4)	0.028 (4)	0.028 (4)	−0.005 (3)	−0.004 (3)	0.003 (3)
C62	0.033 (5)	0.029 (5)	0.025 (4)	−0.001 (4)	−0.003 (4)	−0.003 (4)
C63	0.032 (5)	0.026 (4)	0.033 (4)	−0.011 (4)	−0.005 (4)	−0.003 (4)
C64	0.029 (4)	0.025 (4)	0.036 (5)	−0.010 (4)	−0.004 (4)	0.006 (4)

F1—C3	1.342 (8)	F51—C53	1.332 (8)
F2—C4	1.342 (8)	F52—C54	1.336 (8)
F3—C5	1.326 (8)	F53—C55	1.337 (9)
F4—C6	1.353 (8)	F54—C56	1.348 (8)
F5—C10	1.364 (8)	F55—C60	1.361 (8)
F6—C12	1.365 (9)	F56—C62	1.367 (9)
O1—C1	1.230 (9)	O51—C51	1.240 (8)
O2—C8	1.214 (8)	O52—C58	1.195 (9)
O3—H3	0.840	O53—H53	0.840
O3—C8	1.309 (8)	O53—C58	1.321 (9)
N1—H1	0.880	N51—H51	0.880
N1—C1	1.349 (9)	N51—C51	1.341 (10)
N1—C9	1.416 (9)	N51—C59	1.405 (10)
C1—C2	1.517 (10)	C51—C52	1.504 (10)
C2—C3	1.388 (10)	C52—C53	1.375 (11)
C2—C7	1.408 (10)	C52—C57	1.401 (10)
C3—C4	1.369 (10)	C53—C54	1.384 (11)
C4—C5	1.371 (11)	C54—C55	1.393 (11)
C5—C6	1.400 (11)	C55—C56	1.366 (11)
C6—C7	1.359 (11)	C56—C57	1.371 (11)
C7—C8	1.506 (10)	C57—C58	1.532 (10)
C9—C10	1.396 (11)	C59—C60	1.390 (10)
C9—C14	1.391 (10)	C59—C64	1.391 (11)
C10—C11	1.351 (10)	C60—C61	1.378 (11)
C11—H11	0.950	C61—H61	0.950
C11—C12	1.357 (11)	C61—C62	1.383 (11)
C12—C13	1.399 (11)	C62—C63	1.348 (11)
C13—H13	0.950	C63—H63	0.950
C13—C14	1.378 (11)	C63—C64	1.366 (11)
C14—H14	0.950	C64—H64	0.950
H3—O3—C8	109.5	H53—O53—C58	109.5
H1—N1—C1	118.5	H51—N51—C51	118.6
H1—N1—C9	118.5	H51—N51—C59	118.6
C1—N1—C9	123.0 (6)	C51—N51—C59	122.7 (6)
O1—C1—N1	125.2 (7)	O51—C51—N51	122.9 (6)
O1—C1—C2	119.4 (6)	O51—C51—C52	118.8 (7)
N1—C1—C2	115.4 (6)	N51—C51—C52	118.2 (6)
C1—C2—C3	122.6 (6)	C51—C52—C53	122.1 (7)
C1—C2—C7	118.8 (6)	C51—C52—C57	118.6 (6)
C3—C2—C7	118.1 (7)	C53—C52—C57	119.0 (7)
F1—C3—C2	120.4 (7)	F51—C53—C52	121.6 (6)
F1—C3—C4	118.0 (6)	F51—C53—C54	117.7 (7)
C2—C3—C4	121.6 (7)	C52—C53—C54	120.7 (7)
F2—C4—C3	119.8 (6)	F52—C54—C53	120.1 (7)
F2—C4—C5	119.4 (6)	F52—C54—C55	119.9 (7)
C3—C4—C5	120.8 (7)	C53—C54—C55	119.9 (7)
F3—C5—C4	121.4 (7)	F53—C55—C54	119.4 (7)
F3—C5—C6	120.7 (7)	F53—C55—C56	121.4 (7)
C4—C5—C6	117.9 (7)	C54—C55—C56	119.1 (7)
F4—C6—C5	116.7 (7)	F54—C56—C55	117.6 (6)
F4—C6—C7	120.9 (7)	F54—C56—C57	120.8 (7)
C5—C6—C7	122.3 (7)	C55—C56—C57	121.5 (7)
C2—C7—C6	119.4 (7)	C52—C57—C56	119.8 (7)
C2—C7—C8	119.5 (6)	C52—C57—C58	120.1 (6)
C6—C7—C8	121.0 (6)	C56—C57—C58	120.1 (7)
O2—C8—O3	125.7 (7)	O52—C58—O53	127.9 (7)
O2—C8—C7	122.0 (6)	O52—C58—C57	122.0 (7)
O3—C8—C7	112.3 (6)	O53—C58—C57	110.1 (7)
N1—C9—C10	122.7 (6)	N51—C59—C60	120.9 (7)
N1—C9—C14	119.7 (6)	N51—C59—C64	121.8 (7)
C10—C9—C14	117.5 (7)	C60—C59—C64	117.2 (7)
F5—C10—C9	118.0 (6)	F55—C60—C59	119.2 (6)
F5—C10—C11	118.8 (6)	F55—C60—C61	117.9 (7)
C9—C10—C11	123.2 (7)	C59—C60—C61	122.9 (7)
C10—C11—H11	121.2	C60—C61—H61	122.0
C10—C11—C12	117.6 (7)	C60—C61—C62	116.0 (7)
H11—C11—C12	121.2	H61—C61—C62	122.0
F6—C12—C11	119.5 (7)	F56—C62—C61	117.0 (7)
F6—C12—C13	117.6 (7)	F56—C62—C63	119.6 (7)
C11—C12—C13	122.9 (7)	C61—C62—C63	123.4 (7)
C12—C13—H13	121.1	C62—C63—H63	120.4
C12—C13—C14	117.8 (7)	C62—C63—C64	119.3 (7)
H13—C13—C14	121.1	H63—C63—C64	120.4
C9—C14—C13	120.9 (7)	C59—C64—C63	121.0 (7)
C9—C14—H14	119.6	C59—C64—H64	119.5
C13—C14—H14	119.6	C63—C64—H64	119.5
C9—N1—C1—O1	−7.7 (10)	C59—N51—C51—O51	5.3 (11)
C9—N1—C1—C2	172.3 (6)	C59—N51—C51—C52	−173.6 (6)
O1—C1—C2—C3	131.0 (7)	O51—C51—C52—C53	−130.4 (8)
O1—C1—C2—C7	−40.5 (9)	O51—C51—C52—C57	43.4 (10)
N1—C1—C2—C3	−49.0 (8)	N51—C51—C52—C53	48.5 (10)
N1—C1—C2—C7	139.5 (6)	N51—C51—C52—C57	−137.7 (7)
C1—C2—C3—F1	8.5 (10)	C51—C52—C53—F51	−7.6 (11)
C1—C2—C3—C4	−171.5 (7)	C51—C52—C53—C54	171.8 (7)
C7—C2—C3—F1	−180.0 (6)	C57—C52—C53—F51	178.6 (6)
C7—C2—C3—C4	0.0 (11)	C57—C52—C53—C54	−2.0 (12)
F1—C3—C4—F2	0.0 (10)	F51—C53—C54—F52	−1.1 (11)
F1—C3—C4—C5	179.7 (6)	F51—C53—C54—C55	−178.4 (6)
C2—C3—C4—F2	−180.0 (6)	C52—C53—C54—F52	179.5 (7)
C2—C3—C4—C5	−0.3 (11)	C52—C53—C54—C55	2.2 (12)
F2—C4—C5—F3	0.0 (11)	F52—C54—C55—F53	1.6 (11)
F2—C4—C5—C6	−179.3 (6)	F52—C54—C55—C56	−180.0 (7)
C3—C4—C5—F3	−179.7 (6)	C53—C54—C55—F53	178.9 (7)
C3—C4—C5—C6	1.1 (11)	C53—C54—C55—C56	−2.7 (11)
F3—C5—C6—F4	3.4 (10)	F53—C55—C56—F54	−2.8 (11)
F3—C5—C6—C7	179.1 (7)	F53—C55—C56—C57	−178.5 (6)
C4—C5—C6—F4	−177.4 (6)	C54—C55—C56—F54	178.8 (6)
C4—C5—C6—C7	−1.6 (11)	C54—C55—C56—C57	3.1 (11)
F4—C6—C7—C2	176.9 (6)	F54—C56—C57—C52	−178.4 (6)
F4—C6—C7—C8	−0.8 (11)	F54—C56—C57—C58	1.1 (10)
C5—C6—C7—C2	1.4 (11)	C55—C56—C57—C52	−2.9 (11)
C5—C6—C7—C8	−176.3 (7)	C55—C56—C57—C58	176.6 (7)
C1—C2—C7—C6	171.3 (6)	C51—C52—C57—C56	−171.7 (6)
C1—C2—C7—C8	−11.0 (9)	C51—C52—C57—C58	8.7 (10)
C3—C2—C7—C6	−0.6 (10)	C53—C52—C57—C56	2.3 (11)
C3—C2—C7—C8	177.2 (6)	C53—C52—C57—C58	−177.2 (7)
C2—C7—C8—O2	−57.0 (9)	C52—C57—C58—O52	59.1 (10)
C2—C7—C8—O3	124.7 (7)	C52—C57—C58—O53	−119.9 (7)
C6—C7—C8—O2	120.8 (8)	C56—C57—C58—O52	−120.4 (8)
C6—C7—C8—O3	−57.6 (9)	C56—C57—C58—O53	60.5 (9)
C1—N1—C9—C10	57.0 (9)	C51—N51—C59—C60	−57.9 (10)
C1—N1—C9—C14	−121.9 (7)	C51—N51—C59—C64	123.5 (8)
N1—C9—C10—F5	3.1 (10)	N51—C59—C60—F55	−3.9 (11)
N1—C9—C10—C11	−178.6 (7)	N51—C59—C60—C61	176.7 (7)
C14—C9—C10—F5	−178.0 (6)	C64—C59—C60—F55	174.8 (6)
C14—C9—C10—C11	0.3 (11)	C64—C59—C60—C61	−4.6 (11)
F5—C10—C11—C12	177.0 (6)	F55—C60—C61—C62	−176.8 (6)
C9—C10—C11—C12	−1.3 (11)	C59—C60—C61—C62	2.6 (11)
C10—C11—C12—F6	−179.7 (7)	C60—C61—C62—F56	−177.2 (7)
C10—C11—C12—C13	0.1 (11)	C60—C61—C62—C63	0.6 (12)
F6—C12—C13—C14	−178.1 (6)	F56—C62—C63—C64	176.3 (7)
C11—C12—C13—C14	2.1 (11)	C61—C62—C63—C64	−1.5 (12)
C12—C13—C14—C9	−3.1 (10)	C62—C63—C64—C59	−0.7 (12)
N1—C9—C14—C13	−179.1 (6)	N51—C59—C64—C63	−177.7 (7)
C10—C9—C14—C13	1.9 (10)	C60—C59—C64—C63	3.6 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1i	0.84	1.84	2.666 (6)	168
N1—H1···O2ii	0.88	2.09	2.902 (7)	154
O53—H53···O51iii	0.84	1.84	2.675 (6)	170
N51—H51···O52iv	0.88	2.07	2.902 (8)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1i	0.84	1.84	2.666 (6)	168
N1—H1⋯O2ii	0.88	2.09	2.902 (7)	154
O53—H53⋯O51iii	0.84	1.84	2.675 (6)	170
N51—H51⋯O52iv	0.88	2.07	2.902 (8)	157

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