2-Amino-3,4,5,6-tetra-fluoro-benzoic acid.

The asymmetric unit of the title compound, C(7)H(3)F(4)NO(2), obtained as an inter-mediate in the synthesis of a coupling reagent, contains four independent and conformationally similar mol-ecules. The amine H atoms form both intra-molecular and inter-molecular N-H⋯O(carbox-yl) hydrogen bonds which, together with inter-molecular O-H⋯O(carbox-yl) hydrogen bonds and N-H⋯F associations form ribbon structures along the a axis.

Related literature

The title compound was obtained as one of the inter­mediates in the synthesis of a coupling reagent (Xu et al., 2008 ▶; Liao et al., 2007 ▶), using the Hofmann rearrangement (Perumal & Muthialu, 2004 ▶) with 2-carboxyl-3,4,5,6-tetra­fluoro­benzamide (Cai et al., 1992 ▶).

Experimental

Crystal data

C7H3F4NO2

M = 209.10

Triclinic,

a = 11.0367 (11) Å

b = 11.3664 (11) Å

c = 12.5702 (12) Å

α = 80.378 (8)°

β = 79.764 (8)°

γ = 82.011 (8)°

V = 1520.2 (3) Å3

Z = 8

Cu Kα radiation

μ = 1.79 mm−1

T = 295 K

0.50 × 0.30 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.392, T max = 1.000

8708 measured reflections

4791 independent reflections

3521 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.177

S = 1.05

4791 reflections

533 parameters

16 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global. DOI: 10.1107/S1600536811023087/zs2117sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811023087/zs2117globalsup2.cml

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

C7H3F4NO2	Z = 8
Mr = 209.10	F(000) = 832
Triclinic, P1	Dx = 1.827 Mg m−3
a = 11.0367 (11) Å	Cu Kα radiation, λ = 1.5418 Å
b = 11.3664 (11) Å	Cell parameters from 4167 reflections
c = 12.5702 (12) Å	θ = 3.6–62.7°
α = 80.378 (8)°	µ = 1.79 mm−1
β = 79.764 (8)°	T = 295 K
γ = 82.011 (8)°	Plate, pale yellow
V = 1520.2 (3) Å3	0.50 × 0.30 × 0.15 mm

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra CCD diffractometer	4791 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	3521 reflections with I > 2σ(I)
mirror	Rint = 0.031
Detector resolution: 16.0288 pixels mm-1	θmax = 62.8°, θmin = 3.6°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→13
Tmin = 0.392, Tmax = 1.000	l = −14→14
8708 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0935P)2 + 0.6844P] where P = (Fo2 + 2Fc2)/3
4791 reflections	(Δ/σ)max < 0.001
533 parameters	Δρmax = 0.43 e Å−3
16 restraints	Δρmin = −0.24 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
F16	0.18790 (19)	0.2980 (2)	0.63873 (16)	0.0672 (6)
F13	−0.0401 (2)	0.42992 (19)	0.28267 (16)	0.0682 (6)
F14	0.1447 (2)	0.54588 (19)	0.30496 (17)	0.0701 (6)
O8	−0.1849 (2)	0.2707 (2)	0.3563 (2)	0.0632 (7)
H8	−0.2349	0.2248	0.3531	0.095*
F15	0.2604 (2)	0.4812 (2)	0.48248 (19)	0.0747 (6)
O5	−0.1389 (2)	0.1291 (2)	0.49241 (19)	0.0622 (7)
C22	0.0365 (3)	0.2621 (3)	0.5411 (2)	0.0441 (7)
N3	0.0065 (3)	0.1737 (3)	0.6245 (2)	0.0581 (8)
C32	0.1097 (3)	0.4535 (3)	0.3810 (3)	0.0502 (8)
C33	−0.1201 (3)	0.2250 (3)	0.4350 (2)	0.0470 (7)
C34	−0.0239 (3)	0.2952 (3)	0.4488 (2)	0.0443 (7)
C37	0.0151 (3)	0.3923 (3)	0.3714 (2)	0.0456 (7)
C42	0.1311 (3)	0.3284 (3)	0.5489 (3)	0.0491 (8)
C51	0.1684 (3)	0.4208 (3)	0.4715 (3)	0.0524 (8)
F8	0.3963 (2)	0.21194 (19)	0.48315 (16)	0.0667 (6)
O9	0.2802 (2)	0.0302 (2)	0.5375 (2)	0.0615 (6)
H9	0.2341	−0.0183	0.5317	0.092*
O7	0.3410 (2)	−0.1190 (2)	0.6616 (2)	0.0627 (7)
F5	0.6708 (2)	0.0512 (2)	0.8060 (2)	0.0892 (8)
F6	0.6953 (2)	0.2663 (2)	0.6819 (2)	0.0787 (7)
F7	0.5568 (2)	0.3471 (2)	0.5210 (2)	0.0827 (7)
C28	0.4414 (3)	0.0572 (3)	0.6287 (2)	0.0462 (7)
C35	0.5150 (3)	0.0154 (3)	0.7126 (3)	0.0531 (8)
C40	0.5419 (3)	0.2401 (3)	0.5830 (3)	0.0577 (9)
C44	0.5992 (3)	0.0896 (3)	0.7262 (3)	0.0601 (9)
C47	0.3507 (3)	−0.0174 (3)	0.6118 (2)	0.0469 (7)
C49	0.4586 (3)	0.1696 (3)	0.5659 (3)	0.0498 (8)
N2	0.5075 (4)	−0.0899 (3)	0.7795 (3)	0.0833 (12)
C56	0.6129 (3)	0.1984 (3)	0.6649 (3)	0.0583 (9)
F4	0.0302 (2)	0.94676 (19)	0.75391 (15)	0.0700 (6)
O11	0.1722 (2)	1.0628 (2)	0.82373 (17)	0.0570 (6)
H11	0.2109	1.1185	0.8268	0.085*
O4	0.2335 (2)	0.9962 (2)	0.98460 (19)	0.0594 (6)
F3	−0.1220 (2)	0.7811 (2)	0.78819 (17)	0.0745 (6)
F2	−0.1394 (2)	0.6232 (2)	0.97776 (19)	0.0815 (7)
F1	−0.0109 (2)	0.6443 (2)	1.13507 (17)	0.0810 (7)
N1	0.1387 (3)	0.8133 (3)	1.1147 (2)	0.0620 (8)
C29	0.0014 (3)	0.7205 (3)	1.0410 (3)	0.0543 (8)
C31	0.0926 (3)	0.8903 (3)	0.9301 (2)	0.0432 (7)
C36	0.0799 (3)	0.8091 (3)	1.0291 (2)	0.0471 (7)
C39	−0.0549 (3)	0.7890 (3)	0.8658 (3)	0.0544 (8)
C41	−0.0645 (3)	0.7095 (3)	0.9618 (3)	0.0565 (9)
C43	0.0231 (3)	0.8750 (3)	0.8509 (2)	0.0473 (7)
C46	0.1720 (3)	0.9855 (3)	0.9152 (2)	0.0464 (7)
F12	0.4204 (2)	0.75684 (19)	−0.01077 (18)	0.0705 (6)
F11	0.2839 (2)	0.5761 (2)	0.0206 (2)	0.0766 (7)
O10	0.6074 (3)	0.8442 (2)	0.0225 (2)	0.0687 (7)
H10	0.6552	0.8943	0.0195	0.103*
O1	0.6965 (2)	0.7627 (2)	0.1668 (2)	0.0632 (7)
C26	0.5475 (3)	0.6595 (3)	0.1206 (2)	0.0451 (7)
F10	0.3353 (2)	0.3778 (2)	0.1668 (2)	0.0847 (7)
F9	0.5247 (3)	0.3629 (2)	0.2782 (2)	0.1045 (10)
C38	0.4484 (3)	0.6618 (3)	0.0631 (3)	0.0487 (8)
N4	0.6652 (4)	0.5390 (3)	0.2570 (3)	0.0928 (14)
C48	0.3770 (3)	0.5711 (3)	0.0787 (3)	0.0544 (8)
C50	0.6226 (3)	0.7589 (3)	0.1051 (3)	0.0497 (8)
C53	0.5726 (4)	0.5559 (3)	0.1963 (3)	0.0582 (9)
C54	0.4979 (4)	0.4638 (3)	0.2087 (3)	0.0660 (10)
C55	0.4029 (4)	0.4695 (3)	0.1527 (3)	0.0597 (9)
H3A	0.059 (3)	0.147 (3)	0.667 (2)	0.072*
H3B	−0.039 (3)	0.123 (3)	0.615 (3)	0.072*
H2A	0.551 (3)	−0.113 (3)	0.828 (2)	0.100*
H2B	0.463 (3)	−0.140 (2)	0.768 (3)	0.100*
H1A	0.129 (3)	0.760 (3)	1.1720 (19)	0.074*
H1B	0.186 (3)	0.866 (3)	1.112 (3)	0.074*
H4A	0.681 (3)	0.476 (2)	0.299 (3)	0.107*
H4B	0.713 (3)	0.595 (2)	0.249 (3)	0.107*

	U11	U22	U33	U12	U13	U23
F16	0.0711 (13)	0.0830 (14)	0.0560 (11)	−0.0196 (11)	−0.0327 (10)	−0.0008 (10)
F13	0.0819 (14)	0.0688 (13)	0.0578 (11)	−0.0236 (11)	−0.0350 (10)	0.0176 (10)
F14	0.0769 (14)	0.0623 (13)	0.0693 (13)	−0.0277 (11)	−0.0150 (11)	0.0155 (10)
O8	0.0711 (16)	0.0587 (15)	0.0679 (15)	−0.0207 (12)	−0.0400 (13)	0.0094 (12)
F15	0.0702 (14)	0.0751 (14)	0.0891 (15)	−0.0329 (11)	−0.0289 (11)	−0.0035 (12)
O5	0.0732 (16)	0.0615 (15)	0.0586 (14)	−0.0300 (13)	−0.0300 (12)	0.0119 (12)
C22	0.0460 (17)	0.0459 (17)	0.0392 (15)	−0.0039 (14)	−0.0091 (13)	−0.0018 (13)
N3	0.0614 (18)	0.0679 (19)	0.0467 (15)	−0.0201 (15)	−0.0227 (13)	0.0121 (14)
C32	0.0527 (19)	0.0426 (17)	0.0533 (18)	−0.0106 (15)	−0.0077 (15)	0.0028 (15)
C33	0.0510 (18)	0.0487 (18)	0.0421 (16)	−0.0080 (15)	−0.0120 (14)	−0.0019 (14)
C34	0.0477 (17)	0.0444 (17)	0.0414 (15)	−0.0077 (14)	−0.0125 (13)	0.0001 (13)
C37	0.0526 (18)	0.0442 (17)	0.0402 (16)	−0.0077 (14)	−0.0163 (13)	0.0046 (13)
C42	0.0504 (18)	0.0532 (19)	0.0455 (16)	−0.0057 (15)	−0.0171 (14)	−0.0023 (15)
C51	0.0479 (18)	0.055 (2)	0.0574 (19)	−0.0131 (15)	−0.0134 (15)	−0.0069 (16)
F8	0.0722 (13)	0.0644 (13)	0.0647 (12)	−0.0157 (10)	−0.0253 (10)	0.0096 (10)
O9	0.0639 (15)	0.0617 (15)	0.0664 (15)	−0.0199 (12)	−0.0318 (12)	0.0028 (12)
O7	0.0704 (16)	0.0519 (14)	0.0726 (15)	−0.0180 (12)	−0.0341 (13)	0.0049 (12)
F5	0.0981 (18)	0.0973 (18)	0.0898 (16)	−0.0335 (14)	−0.0588 (14)	0.0020 (14)
F6	0.0734 (14)	0.0865 (16)	0.0894 (15)	−0.0374 (12)	−0.0187 (12)	−0.0206 (13)
F7	0.0925 (17)	0.0697 (14)	0.0882 (16)	−0.0367 (13)	−0.0184 (13)	0.0091 (12)
C28	0.0464 (17)	0.0485 (18)	0.0459 (17)	−0.0093 (14)	−0.0086 (14)	−0.0083 (14)
C35	0.059 (2)	0.054 (2)	0.0506 (18)	−0.0128 (16)	−0.0177 (15)	−0.0036 (15)
C40	0.062 (2)	0.052 (2)	0.060 (2)	−0.0190 (17)	−0.0034 (17)	−0.0053 (16)
C44	0.064 (2)	0.068 (2)	0.056 (2)	−0.0163 (19)	−0.0233 (17)	−0.0101 (18)
C47	0.0461 (17)	0.0507 (19)	0.0457 (16)	−0.0047 (14)	−0.0126 (13)	−0.0069 (15)
C49	0.0493 (18)	0.056 (2)	0.0443 (16)	−0.0094 (15)	−0.0093 (14)	−0.0033 (15)
N2	0.108 (3)	0.072 (2)	0.084 (2)	−0.037 (2)	−0.061 (2)	0.0190 (19)
C56	0.055 (2)	0.066 (2)	0.060 (2)	−0.0208 (17)	−0.0073 (16)	−0.0166 (18)
F4	0.1041 (17)	0.0657 (13)	0.0480 (11)	−0.0320 (12)	−0.0316 (11)	0.0086 (9)
O11	0.0755 (16)	0.0548 (14)	0.0449 (12)	−0.0271 (12)	−0.0167 (11)	0.0045 (10)
O4	0.0715 (16)	0.0568 (14)	0.0564 (13)	−0.0259 (12)	−0.0274 (12)	0.0074 (11)
F3	0.0953 (16)	0.0776 (14)	0.0655 (13)	−0.0313 (12)	−0.0364 (12)	−0.0099 (11)
F2	0.0936 (17)	0.0807 (15)	0.0808 (15)	−0.0517 (13)	−0.0238 (12)	0.0036 (12)
F1	0.0971 (17)	0.0848 (16)	0.0630 (13)	−0.0440 (13)	−0.0275 (12)	0.0279 (12)
N1	0.069 (2)	0.077 (2)	0.0442 (15)	−0.0264 (16)	−0.0210 (14)	0.0075 (15)
C29	0.059 (2)	0.058 (2)	0.0457 (17)	−0.0195 (17)	−0.0085 (15)	0.0060 (15)
C31	0.0484 (17)	0.0452 (17)	0.0376 (15)	−0.0105 (14)	−0.0079 (13)	−0.0051 (13)
C36	0.0507 (18)	0.0489 (18)	0.0426 (16)	−0.0084 (15)	−0.0100 (13)	−0.0043 (14)
C39	0.063 (2)	0.060 (2)	0.0478 (18)	−0.0139 (17)	−0.0203 (15)	−0.0117 (16)
C41	0.061 (2)	0.053 (2)	0.059 (2)	−0.0229 (17)	−0.0120 (16)	−0.0037 (16)
C43	0.061 (2)	0.0457 (17)	0.0366 (15)	−0.0092 (15)	−0.0140 (14)	−0.0014 (13)
C46	0.0519 (18)	0.0437 (17)	0.0436 (16)	−0.0070 (14)	−0.0087 (14)	−0.0043 (14)
F12	0.0690 (13)	0.0618 (13)	0.0836 (14)	−0.0162 (10)	−0.0357 (11)	0.0138 (11)
F11	0.0623 (13)	0.0722 (14)	0.1048 (17)	−0.0188 (11)	−0.0332 (12)	−0.0095 (13)
O10	0.0822 (18)	0.0604 (15)	0.0701 (16)	−0.0318 (13)	−0.0379 (14)	0.0190 (13)
O1	0.0750 (16)	0.0601 (15)	0.0614 (14)	−0.0257 (13)	−0.0317 (13)	0.0084 (12)
C26	0.0489 (17)	0.0449 (17)	0.0435 (16)	−0.0083 (14)	−0.0119 (13)	−0.0044 (14)
F10	0.0967 (18)	0.0647 (14)	0.1022 (17)	−0.0426 (13)	−0.0251 (14)	−0.0014 (13)
F9	0.155 (3)	0.0682 (15)	0.1023 (19)	−0.0487 (17)	−0.0663 (18)	0.0320 (14)
C38	0.0496 (18)	0.0476 (18)	0.0487 (17)	−0.0077 (15)	−0.0109 (14)	−0.0010 (14)
N4	0.129 (3)	0.061 (2)	0.105 (3)	−0.040 (2)	−0.079 (3)	0.028 (2)
C48	0.0472 (19)	0.059 (2)	0.062 (2)	−0.0116 (16)	−0.0123 (15)	−0.0159 (17)
C50	0.0506 (18)	0.0513 (19)	0.0488 (17)	−0.0112 (15)	−0.0113 (14)	−0.0038 (15)
C53	0.070 (2)	0.056 (2)	0.0538 (19)	−0.0184 (18)	−0.0208 (17)	−0.0015 (16)
C54	0.094 (3)	0.049 (2)	0.058 (2)	−0.023 (2)	−0.0221 (19)	0.0061 (17)
C55	0.068 (2)	0.051 (2)	0.064 (2)	−0.0235 (17)	−0.0069 (18)	−0.0102 (17)

F16—C42	1.360 (3)	F4—C43	1.345 (3)
F13—C37	1.344 (3)	O11—H11	0.8200
F14—C32	1.346 (4)	O11—C46	1.325 (4)
O8—H8	0.8200	O4—C46	1.227 (4)
O8—C33	1.318 (4)	F3—C39	1.346 (4)
F15—C51	1.341 (4)	F2—C41	1.337 (4)
O5—C33	1.224 (4)	F1—C29	1.341 (4)
C22—N3	1.354 (4)	N1—C36	1.362 (4)
C22—C34	1.412 (4)	N1—H1A	0.859 (17)
C22—C42	1.396 (5)	N1—H1B	0.846 (17)
N3—H3A	0.855 (17)	C29—C36	1.390 (5)
N3—H3B	0.854 (17)	C29—C41	1.364 (5)
C32—C37	1.365 (5)	C31—C36	1.417 (4)
C32—C51	1.381 (5)	C31—C43	1.406 (4)
C33—C34	1.463 (4)	C31—C46	1.454 (4)
C34—C37	1.405 (4)	C39—C41	1.379 (5)
C42—C51	1.361 (5)	C39—C43	1.360 (5)
F8—C49	1.335 (4)	F12—C38	1.341 (4)
O9—H9	0.8200	F11—C48	1.353 (4)
O9—C47	1.320 (4)	O10—H10	0.8200
O7—C47	1.228 (4)	O10—C50	1.314 (4)
F5—C44	1.363 (4)	O1—C50	1.229 (4)
F6—C56	1.337 (4)	C26—C38	1.410 (5)
F7—C40	1.344 (4)	C26—C50	1.460 (4)
C28—C35	1.424 (4)	C26—C53	1.413 (5)
C28—C47	1.462 (4)	F10—C55	1.334 (4)
C28—C49	1.403 (5)	F9—C54	1.353 (4)
C35—C44	1.388 (5)	C38—C48	1.351 (5)
C35—N2	1.347 (5)	N4—C53	1.356 (5)
C40—C49	1.367 (5)	N4—H4A	0.827 (17)
C40—C56	1.385 (5)	N4—H4B	0.869 (17)
C44—C56	1.356 (5)	C48—C55	1.388 (5)
N2—H2A	0.829 (17)	C53—C54	1.393 (5)
N2—H2B	0.851 (17)	C54—C55	1.352 (5)
C33—O8—H8	109.5	C46—O11—H11	109.5
N3—C22—C34	124.9 (3)	C36—N1—H1A	120 (2)
N3—C22—C42	117.6 (3)	C36—N1—H1B	121 (2)
C42—C22—C34	117.4 (3)	H1A—N1—H1B	119 (3)
C22—N3—H3A	118 (2)	F1—C29—C36	118.3 (3)
C22—N3—H3B	119 (2)	F1—C29—C41	119.1 (3)
H3A—N3—H3B	115 (3)	C41—C29—C36	122.6 (3)
F14—C32—C37	121.1 (3)	C36—C31—C46	120.2 (3)
F14—C32—C51	119.9 (3)	C43—C31—C36	116.8 (3)
C37—C32—C51	119.0 (3)	C43—C31—C46	123.0 (3)
O8—C33—C34	116.0 (3)	N1—C36—C29	117.5 (3)
O5—C33—O8	121.8 (3)	N1—C36—C31	124.0 (3)
O5—C33—C34	122.2 (3)	C29—C36—C31	118.5 (3)
C22—C34—C33	119.3 (3)	F3—C39—C41	120.3 (3)
C37—C34—C22	117.9 (3)	F3—C39—C43	120.7 (3)
C37—C34—C33	122.7 (3)	C43—C39—C41	119.0 (3)
F13—C37—C32	116.2 (3)	F2—C41—C29	120.2 (3)
F13—C37—C34	121.0 (3)	F2—C41—C39	120.1 (3)
C32—C37—C34	122.8 (3)	C29—C41—C39	119.7 (3)
F16—C42—C22	117.5 (3)	F4—C43—C31	121.1 (3)
F16—C42—C51	119.2 (3)	F4—C43—C39	115.5 (3)
C51—C42—C22	123.3 (3)	C39—C43—C31	123.4 (3)
F15—C51—C32	119.5 (3)	O11—C46—C31	116.6 (3)
F15—C51—C42	121.0 (3)	O4—C46—O11	121.3 (3)
C42—C51—C32	119.5 (3)	O4—C46—C31	122.0 (3)
C47—O9—H9	109.5	C50—O10—H10	109.5
C35—C28—C47	119.2 (3)	C38—C26—C50	122.7 (3)
C49—C28—C35	118.2 (3)	C38—C26—C53	117.4 (3)
C49—C28—C47	122.6 (3)	C53—C26—C50	119.9 (3)
C44—C35—C28	117.2 (3)	F12—C38—C26	120.4 (3)
N2—C35—C28	124.5 (3)	F12—C38—C48	116.6 (3)
N2—C35—C44	118.3 (3)	C48—C38—C26	123.0 (3)
F7—C40—C49	121.2 (3)	C53—N4—H4A	123 (2)
F7—C40—C56	120.2 (3)	C53—N4—H4B	118 (2)
C49—C40—C56	118.6 (3)	H4A—N4—H4B	118 (3)
F5—C44—C35	118.1 (3)	F11—C48—C55	119.7 (3)
C56—C44—F5	118.6 (3)	C38—C48—F11	121.1 (3)
C56—C44—C35	123.3 (3)	C38—C48—C55	119.2 (3)
O9—C47—C28	116.0 (3)	O10—C50—C26	116.9 (3)
O7—C47—O9	121.3 (3)	O1—C50—O10	121.6 (3)
O7—C47—C28	122.8 (3)	O1—C50—C26	121.5 (3)
F8—C49—C28	121.3 (3)	N4—C53—C26	124.7 (3)
F8—C49—C40	116.1 (3)	N4—C53—C54	117.5 (3)
C40—C49—C28	122.6 (3)	C54—C53—C26	117.8 (3)
C35—N2—H2A	123 (2)	F9—C54—C53	117.9 (3)
C35—N2—H2B	120 (2)	C55—C54—F9	118.9 (3)
H2A—N2—H2B	117 (3)	C55—C54—C53	123.2 (3)
F6—C56—C40	119.2 (3)	F10—C55—C48	119.9 (3)
F6—C56—C44	120.7 (3)	F10—C55—C54	120.7 (3)
C44—C56—C40	120.2 (3)	C54—C55—C48	119.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···F1	0.86 (3)	2.31 (3)	2.655 (4)	104 (2)
N1—H1B···O4	0.84 (3)	2.04 (4)	2.637 (4)	128 (3)
N1—H1B···F5i	0.84 (3)	2.40 (3)	3.154 (4)	150 (3)
N2—H2A···F5	0.83 (3)	2.39 (3)	2.670 (5)	101 (2)
N2—H2A···O10ii	0.83 (3)	2.58 (3)	3.363 (5)	158 (3)
N2—H2B···O7	0.85 (3)	2.03 (4)	2.643 (5)	129 (3)
N3—H3A···F4iii	0.85 (3)	2.39 (3)	2.816 (4)	112 (3)
N3—H3A···F16	0.85 (3)	2.32 (3)	2.652 (4)	104 (2)
N3—H3A···O11iii	0.85 (3)	2.50 (3)	3.337 (4)	167 (3)
N3—H3B···O5	0.85 (3)	2.04 (4)	2.654 (4)	129 (3)
N4—H4A···F9	0.83 (3)	2.36 (3)	2.650 (5)	101 (3)
N4—H4B···O1	0.86 (3)	2.01 (3)	2.648 (4)	130 (3)
N4—H4B···F16iv	0.86 (3)	2.48 (3)	3.191 (5)	140 (3)
O9—H9···O5v	0.82	1.84	2.660 (3)	175
O10—H10···O4vi	0.82	1.86	2.675 (4)	178
O11—H11···O1vi	0.82	1.82	2.643 (3)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O4	0.84 (3)	2.04 (4)	2.637 (4)	128 (3)
N1—H1B⋯F5i	0.84 (3)	2.40 (3)	3.154 (4)	150 (3)
N2—H2A⋯O10ii	0.83 (3)	2.58 (3)	3.363 (5)	158 (3)
N2—H2B⋯O7	0.85 (3)	2.03 (4)	2.643 (5)	129 (3)
N3—H3A⋯O11iii	0.85 (3)	2.50 (3)	3.337 (4)	167 (3)
N3—H3B⋯O5	0.85 (3)	2.04 (4)	2.654 (4)	129 (3)
N4—H4B⋯O1	0.86 (3)	2.01 (3)	2.648 (4)	130 (3)
N4—H4B⋯F16iv	0.86 (3)	2.48 (3)	3.191 (5)	140 (3)
O9—H9⋯O5v	0.82	1.84	2.660 (3)	175
O10—H10⋯O4vi	0.82	1.86	2.675 (4)	178
O11—H11⋯O1vi	0.82	1.82	2.643 (3)	177

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