4-Fluoro-2-(phenyl­amino)­benzoic acid

Li, J.; Long, S.

doi:10.1107/S2414314624001974

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 9| Part 3| March 2024| x240197

https://doi.org/10.1107/S2414314624001974

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4-Fluoro-2-(phenylamino)benzoic acid

Jingxi Li ^a and Sihui Long ^a ^*

^aSchool of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan, Hubei 430205, People's Republic of China
^*Correspondence e-mail: sihuilong@wit.edu.cn

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 30 October 2023; accepted 29 February 2024; online 6 March 2024)

The title compound, C₁₃H₁₀FNO₂, was obtained by the reaction of 2-bromo-4-fluorobenzoic acid with aniline. There are two independent molecules, A and B, in the asymmetric unit, with slight conformational differences: the dihedral angles between the aromatic rings are 55.63 (5) and 52.65 (5)°. Both molecules feature an intramolecular N—H⋯O hydrogen bond. In the crystal, the molecules are linked by pairwise O—H⋯O hydrogen bonds to form A–B acid–acid dimers and weak C—H⋯F interactions further connect the dimers.

Keywords: Z′ = 2; twisted conformation; acid–acid dimer; crystal structure.

CCDC reference: 2336149

Structure description

Non-steroidal anti-inflammatory drugs are among the most commonly utilized medicines globally (Abdu et al., 2020 ). They exhibit anti-inflammatory, antipyretic, and analgesic properties. They are available as both prescription and over-the-counter medications and are employed to treat fever, acute or chronic pain, and various inflammatory conditions such as osteoarthritis and rheumatoid arthritis (Brennan et al., 2021 ). Anthranilic acid derivatives represent a crucial subset of non-steroidal anti-inflammatory drugs.

The title compound (Fig. 1), an anthranilic acid derivative, was synthesized employing the Ullmann reaction (Sambiagio et al., 2014 ). Crystallization from acetone solution led to suitable single crystals for structure determination by single-crystal X-ray diffraction, which revealed the asymmetric unit to consist of two molecules, A (containing C1A) and B (containing C1B) (Fig. 1). The dihedral angles between the C1A–C6A/C8A–C13A and C1B–C6B/C8B–C13B aromatic rings are 55.63 (5) and 52.65 (5)°, respectively. Both molecules feature an intramolecular N—H⋯O hydrogen bond (Table 1). In the extended structure, the molecules form A–B dimers by way of pairwise O—H⋯O hydrogen bonds (Fig. 2, Table 1). Two weak C—H⋯F interactions are also observed.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7A—H7A⋯O15A	0.88	1.98	2.673 (2)	135
N7B—H7B⋯O15B	0.88	1.98	2.6770 (19)	136
O16A—H16A⋯O15Bⁱ	0.84	1.80	2.6413 (19)	176
O16B—H16B⋯O15Aⁱ	0.84	1.77	2.6099 (19)	174
C4A—H4A⋯F1Bⁱⁱ	0.95	2.48	3.426 (2)	174
C4B—H4B⋯F1Aⁱⁱ	0.95	2.52	3.464 (2)	173
Symmetry codes: (i) ; (ii) .

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Figure 2
Packing of the molecules in the crystal (for clarity, H atoms not involved in hydrogen bonding are omitted). The C1A molecule is shown in red and the C1B molecule in blue.

Synthesis and crystallization

The title compound was prepared by reacting 2-bromo-4-fluorobenzoic acid and aniline in the presence of a Cu catalyst at 403 K (Fig. 3). The product was purified by column chromatography. Single crystals were obtained by slowly evaporating an acetone solution of the title compound.

Figure 3
Synthesis of the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₁₀FNO₂
M_r	231.22
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	90
a, b, c (Å)	9.9550 (3), 10.0060 (3), 11.3320 (4)
α, β, γ (°)	89.4150 (14), 78.0130 (14), 78.9010 (14)
V (Å³)	1082.99 (6)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	0.40 × 0.10 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997 )
T_min, T_max	0.958, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	9760, 4918, 2625
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.131, 0.94
No. of reflections	4918
No. of parameters	309
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.29
Computer programs: COLLECT (Nonius, 2002 ), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 and SHELXL97 (Sheldrick, 2015 ) and XP in SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 2336149

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314624001974/hb4457sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624001974/hb4457Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314624001974/hb4457Isup3.cml

checkCIF report

Computing details top

4-Fluoro-2-(phenylamino)benzoic acid top

Crystal data top

C₁₃H₁₀FNO₂	Z = 4
M_r = 231.22	F(000) = 480
Triclinic, P1	D_x = 1.418 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9550 (3) Å	Cell parameters from 4887 reflections
b = 10.0060 (3) Å	θ = 1.0–27.5°
c = 11.3320 (4) Å	µ = 0.11 mm⁻¹
α = 89.4150 (14)°	T = 90 K
β = 78.0130 (14)°	Rod, colorless
γ = 78.9010 (14)°	0.40 × 0.10 × 0.10 mm
V = 1082.99 (6) Å³

Data collection top

Nonius KappaCCD diffractometer	4918 independent reflections
Radiation source: fine-focus sealed tube	2625 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
Detector resolution: 18 pixels mm^-1	θ_max = 27.4°, θ_min = 1.8°
ω scans at fixed χ=55°	h = −12→12
Absorption correction: multi-scan (Scalepack; Otwinowski & Minor, 1997)	k = −12→12
T_min = 0.958, T_max = 0.989	l = −14→14
9760 measured reflections

Refinement top

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0609P)²] where P = (F_o² + 2F_c²)/3
4918 reflections	(Δ/σ)_max = 0.001
309 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Special details top

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.

The positions of the H atoms attached to the N and O atoms were obtained from a difference Fourier map, which were then relocated to idealised locations. The C-bound H atoms were positioned geometrically with C—H = 0.95 Å and refined as riding atoms. The constraint U_iso(H) = 1.2U_eq(C,N) or 1.5U_eq(O) was applied in all cases.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1B	0.33716 (12)	0.00814 (11)	0.33502 (9)	0.0289 (3)
C1B	0.5768 (2)	0.24263 (18)	0.29666 (16)	0.0187 (4)
C2B	0.5628 (2)	0.28222 (18)	0.41950 (15)	0.0180 (4)
C3B	0.4705 (2)	0.22914 (18)	0.50929 (16)	0.0209 (5)
H3B	0.4611	0.2575	0.5908	0.025*
C4B	0.3924 (2)	0.13739 (19)	0.48453 (16)	0.0213 (5)
H4B	0.3298	0.1019	0.5463	0.026*
C5B	0.4108 (2)	0.09982 (19)	0.36367 (17)	0.0207 (5)
C6B	0.4976 (2)	0.14842 (18)	0.27121 (16)	0.0214 (5)
H6B	0.5047	0.1190	0.1903	0.026*
N7B	0.66309 (17)	0.29688 (16)	0.20633 (13)	0.0233 (4)
H7B	0.7129	0.3520	0.2288	0.028*
C8B	0.6802 (2)	0.2731 (2)	0.08018 (16)	0.0216 (5)
C9B	0.7158 (2)	0.1412 (2)	0.02896 (16)	0.0255 (5)
H9B	0.7313	0.0645	0.0780	0.031*
C10B	0.7281 (2)	0.1238 (2)	−0.09443 (17)	0.0281 (5)
H10B	0.7496	0.0343	−0.1294	0.034*
C11B	0.7098 (2)	0.2344 (2)	−0.16717 (17)	0.0299 (5)
H11B	0.7185	0.2214	−0.2515	0.036*
C12B	0.6787 (2)	0.3644 (2)	−0.11607 (17)	0.0305 (5)
H12B	0.6678	0.4410	−0.1659	0.037*
C13B	0.6633 (2)	0.3839 (2)	0.00710 (16)	0.0262 (5)
H13B	0.6411	0.4736	0.0415	0.031*
C14B	0.6411 (2)	0.38018 (19)	0.45451 (16)	0.0191 (4)
O15B	0.71882 (13)	0.44023 (12)	0.38231 (10)	0.0216 (3)
O16B	0.62152 (14)	0.40054 (13)	0.57300 (10)	0.0231 (3)
H16B	0.6748	0.4510	0.5876	0.035*
F1A	−0.15859 (12)	0.01065 (11)	0.31096 (10)	0.0312 (3)
C1A	0.0766 (2)	0.24951 (19)	0.27856 (16)	0.0209 (5)
C2A	0.06407 (19)	0.28389 (18)	0.40285 (16)	0.0185 (4)
C3A	−0.0259 (2)	0.22559 (19)	0.49136 (17)	0.0211 (5)
H3A	−0.0339	0.2495	0.5738	0.025*
C4A	−0.1028 (2)	0.13494 (19)	0.46294 (17)	0.0231 (5)
H4A	−0.1640	0.0964	0.5235	0.028*
C5A	−0.0867 (2)	0.10265 (19)	0.34142 (17)	0.0229 (5)
C6A	−0.0025 (2)	0.15615 (18)	0.25109 (17)	0.0225 (5)
H6A	0.0030	0.1306	0.1694	0.027*
N7A	0.16563 (18)	0.30209 (17)	0.18986 (13)	0.0272 (4)
H7A	0.2212	0.3499	0.2136	0.033*
C8A	0.1777 (2)	0.28748 (19)	0.06299 (16)	0.0233 (5)
C9A	0.0611 (2)	0.3164 (2)	0.01172 (18)	0.0324 (5)
H9A	−0.0292	0.3448	0.0615	0.039*
C10A	0.0762 (2)	0.3039 (2)	−0.11224 (18)	0.0343 (6)
H10A	−0.0043	0.3216	−0.1470	0.041*
C11A	0.2074 (2)	0.2658 (2)	−0.18536 (18)	0.0299 (5)
H11A	0.2176	0.2581	−0.2704	0.036*
C12A	0.3237 (2)	0.2389 (2)	−0.13428 (16)	0.0287 (5)
H12A	0.4142	0.2135	−0.1846	0.034*
C13A	0.3098 (2)	0.2488 (2)	−0.01033 (17)	0.0262 (5)
H13A	0.3902	0.2291	0.0243	0.031*
C14A	0.1435 (2)	0.37892 (19)	0.43984 (16)	0.0193 (4)
O15A	0.22885 (13)	0.43274 (13)	0.36935 (10)	0.0224 (3)
O16A	0.11716 (14)	0.40479 (13)	0.55831 (10)	0.0222 (3)
H16A	0.1700	0.4553	0.5738	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1B	0.0345 (7)	0.0296 (7)	0.0280 (6)	−0.0177 (6)	−0.0080 (5)	−0.0036 (5)
C1B	0.0189 (11)	0.0165 (10)	0.0214 (10)	−0.0035 (9)	−0.0060 (8)	0.0011 (8)
C2B	0.0186 (11)	0.0170 (10)	0.0188 (10)	−0.0037 (9)	−0.0049 (8)	0.0005 (8)
C3B	0.0239 (12)	0.0185 (11)	0.0193 (10)	−0.0007 (9)	−0.0055 (9)	−0.0032 (8)
C4B	0.0202 (12)	0.0226 (11)	0.0200 (10)	−0.0040 (9)	−0.0021 (9)	0.0001 (8)
C5B	0.0210 (12)	0.0177 (11)	0.0255 (11)	−0.0058 (9)	−0.0077 (9)	−0.0019 (8)
C6B	0.0260 (12)	0.0181 (11)	0.0208 (10)	−0.0027 (9)	−0.0075 (9)	−0.0027 (8)
N7B	0.0285 (10)	0.0287 (10)	0.0176 (8)	−0.0142 (8)	−0.0076 (7)	−0.0002 (7)
C8B	0.0201 (12)	0.0273 (12)	0.0190 (10)	−0.0069 (9)	−0.0056 (9)	−0.0038 (9)
C9B	0.0256 (13)	0.0290 (12)	0.0212 (11)	−0.0030 (10)	−0.0059 (9)	0.0002 (9)
C10B	0.0301 (13)	0.0293 (13)	0.0246 (11)	−0.0065 (10)	−0.0038 (10)	−0.0078 (9)
C11B	0.0337 (14)	0.0421 (14)	0.0163 (10)	−0.0141 (11)	−0.0040 (9)	−0.0042 (10)
C12B	0.0397 (15)	0.0325 (13)	0.0218 (11)	−0.0142 (11)	−0.0054 (10)	0.0041 (9)
C13B	0.0323 (13)	0.0231 (11)	0.0246 (11)	−0.0099 (10)	−0.0051 (9)	−0.0015 (9)
C14B	0.0209 (12)	0.0179 (11)	0.0187 (10)	0.0001 (9)	−0.0080 (9)	−0.0030 (8)
O15B	0.0250 (8)	0.0232 (8)	0.0187 (7)	−0.0093 (6)	−0.0048 (6)	0.0007 (6)
O16B	0.0270 (9)	0.0267 (8)	0.0181 (7)	−0.0109 (6)	−0.0053 (6)	−0.0029 (6)
F1A	0.0329 (7)	0.0277 (7)	0.0367 (7)	−0.0150 (6)	−0.0069 (6)	−0.0049 (5)
C1A	0.0179 (12)	0.0210 (11)	0.0237 (11)	−0.0058 (9)	−0.0021 (9)	−0.0013 (8)
C2A	0.0166 (11)	0.0177 (11)	0.0205 (10)	−0.0010 (8)	−0.0045 (8)	−0.0025 (8)
C3A	0.0188 (12)	0.0204 (11)	0.0231 (10)	−0.0022 (9)	−0.0040 (9)	−0.0002 (8)
C4A	0.0204 (12)	0.0218 (11)	0.0264 (11)	−0.0057 (9)	−0.0023 (9)	0.0039 (9)
C5A	0.0222 (12)	0.0163 (11)	0.0324 (12)	−0.0070 (9)	−0.0076 (9)	0.0001 (9)
C6A	0.0226 (12)	0.0206 (11)	0.0257 (11)	−0.0034 (9)	−0.0081 (9)	−0.0054 (9)
N7A	0.0317 (11)	0.0361 (11)	0.0184 (9)	−0.0189 (9)	−0.0040 (8)	−0.0048 (7)
C8A	0.0291 (13)	0.0243 (12)	0.0203 (10)	−0.0124 (10)	−0.0074 (9)	−0.0021 (8)
C9A	0.0263 (13)	0.0436 (14)	0.0264 (12)	−0.0070 (11)	−0.0029 (10)	−0.0046 (10)
C10A	0.0332 (14)	0.0470 (15)	0.0279 (12)	−0.0103 (11)	−0.0158 (11)	−0.0004 (10)
C11A	0.0392 (15)	0.0322 (13)	0.0211 (11)	−0.0120 (11)	−0.0076 (10)	−0.0006 (9)
C12A	0.0306 (13)	0.0318 (13)	0.0223 (11)	−0.0058 (10)	−0.0022 (10)	−0.0011 (9)
C13A	0.0297 (13)	0.0293 (12)	0.0225 (11)	−0.0086 (10)	−0.0092 (10)	0.0020 (9)
C14A	0.0187 (12)	0.0189 (11)	0.0198 (10)	−0.0013 (9)	−0.0049 (9)	−0.0011 (8)
O15A	0.0254 (8)	0.0252 (8)	0.0187 (7)	−0.0105 (6)	−0.0040 (6)	−0.0008 (6)
O16A	0.0252 (9)	0.0245 (8)	0.0190 (7)	−0.0094 (6)	−0.0055 (6)	−0.0029 (6)

Geometric parameters (Å, º) top

F1B—C5B	1.359 (2)	F1A—C5A	1.357 (2)
C1B—N7B	1.372 (2)	C1A—N7A	1.368 (2)
C1B—C6B	1.407 (3)	C1A—C6A	1.408 (3)
C1B—C2B	1.423 (2)	C1A—C2A	1.428 (2)
C2B—C3B	1.397 (3)	C2A—C3A	1.401 (3)
C2B—C14B	1.468 (3)	C2A—C14A	1.463 (3)
C3B—C4B	1.377 (3)	C3A—C4A	1.375 (3)
C3B—H3B	0.9500	C3A—H3A	0.9500
C4B—C5B	1.390 (2)	C4A—C5A	1.387 (3)
C4B—H4B	0.9500	C4A—H4A	0.9500
C5B—C6B	1.363 (3)	C5A—C6A	1.357 (3)
C6B—H6B	0.9500	C6A—H6A	0.9500
N7B—C8B	1.421 (2)	N7A—C8A	1.424 (2)
N7B—H7B	0.8800	N7A—H7A	0.8800
C8B—C13B	1.382 (3)	C8A—C9A	1.384 (3)
C8B—C9B	1.398 (3)	C8A—C13A	1.388 (3)
C9B—C10B	1.388 (2)	C9A—C10A	1.386 (3)
C9B—H9B	0.9500	C9A—H9A	0.9500
C10B—C11B	1.380 (3)	C10A—C11A	1.380 (3)
C10B—H10B	0.9500	C10A—H10A	0.9500
C11B—C12B	1.381 (3)	C11A—C12A	1.380 (3)
C11B—H11B	0.9500	C11A—H11A	0.9500
C12B—C13B	1.384 (2)	C12A—C13A	1.385 (2)
C12B—H12B	0.9500	C12A—H12A	0.9500
C13B—H13B	0.9500	C13A—H13A	0.9500
C14B—O15B	1.239 (2)	C14A—O15A	1.239 (2)
C14B—O16B	1.3281 (19)	C14A—O16A	1.3315 (19)
O16B—H16B	0.8400	O16A—H16A	0.8400

N7B—C1B—C6B	121.45 (17)	N7A—C1A—C6A	121.31 (17)
N7B—C1B—C2B	120.72 (17)	N7A—C1A—C2A	121.16 (17)
C6B—C1B—C2B	117.82 (17)	C6A—C1A—C2A	117.50 (17)
C3B—C2B—C1B	119.53 (17)	C3A—C2A—C1A	119.52 (18)
C3B—C2B—C14B	118.85 (16)	C3A—C2A—C14A	119.23 (17)
C1B—C2B—C14B	121.61 (17)	C1A—C2A—C14A	121.25 (17)
C4B—C3B—C2B	122.73 (17)	C4A—C3A—C2A	122.23 (18)
C4B—C3B—H3B	118.6	C4A—C3A—H3A	118.9
C2B—C3B—H3B	118.6	C2A—C3A—H3A	118.9
C3B—C4B—C5B	115.89 (18)	C3A—C4A—C5A	116.65 (18)
C3B—C4B—H4B	122.1	C3A—C4A—H4A	121.7
C5B—C4B—H4B	122.1	C5A—C4A—H4A	121.7
F1B—C5B—C6B	117.37 (16)	F1A—C5A—C6A	117.90 (17)
F1B—C5B—C4B	117.99 (17)	F1A—C5A—C4A	117.91 (17)
C6B—C5B—C4B	124.64 (19)	C6A—C5A—C4A	124.19 (19)
C5B—C6B—C1B	119.37 (17)	C5A—C6A—C1A	119.90 (18)
C5B—C6B—H6B	120.3	C5A—C6A—H6A	120.1
C1B—C6B—H6B	120.3	C1A—C6A—H6A	120.1
C1B—N7B—C8B	126.58 (16)	C1A—N7A—C8A	126.76 (16)
C1B—N7B—H7B	116.7	C1A—N7A—H7A	116.6
C8B—N7B—H7B	116.7	C8A—N7A—H7A	116.6
C13B—C8B—C9B	119.77 (17)	C9A—C8A—C13A	119.78 (18)
C13B—C8B—N7B	118.66 (17)	C9A—C8A—N7A	121.23 (18)
C9B—C8B—N7B	121.56 (17)	C13A—C8A—N7A	118.94 (17)
C10B—C9B—C8B	119.15 (18)	C8A—C9A—C10A	120.0 (2)
C10B—C9B—H9B	120.4	C8A—C9A—H9A	120.0
C8B—C9B—H9B	120.4	C10A—C9A—H9A	120.0
C11B—C10B—C9B	121.00 (19)	C11A—C10A—C9A	120.3 (2)
C11B—C10B—H10B	119.5	C11A—C10A—H10A	119.9
C9B—C10B—H10B	119.5	C9A—C10A—H10A	119.9
C10B—C11B—C12B	119.33 (18)	C10A—C11A—C12A	119.62 (19)
C10B—C11B—H11B	120.3	C10A—C11A—H11A	120.2
C12B—C11B—H11B	120.3	C12A—C11A—H11A	120.2
C11B—C12B—C13B	120.53 (19)	C11A—C12A—C13A	120.6 (2)
C11B—C12B—H12B	119.7	C11A—C12A—H12A	119.7
C13B—C12B—H12B	119.7	C13A—C12A—H12A	119.7
C8B—C13B—C12B	120.17 (18)	C12A—C13A—C8A	119.67 (19)
C8B—C13B—H13B	119.9	C12A—C13A—H13A	120.2
C12B—C13B—H13B	119.9	C8A—C13A—H13A	120.2
O15B—C14B—O16B	121.64 (17)	O15A—C14A—O16A	121.23 (17)
O15B—C14B—C2B	124.45 (16)	O15A—C14A—C2A	124.38 (16)
O16B—C14B—C2B	113.91 (16)	O16A—C14A—C2A	114.38 (16)
C14B—O16B—H16B	109.5	C14A—O16A—H16A	109.5

N7B—C1B—C2B—C3B	177.69 (17)	N7A—C1A—C2A—C3A	−178.56 (18)
C6B—C1B—C2B—C3B	−1.2 (3)	C6A—C1A—C2A—C3A	−0.6 (3)
N7B—C1B—C2B—C14B	−1.0 (3)	N7A—C1A—C2A—C14A	1.4 (3)
C6B—C1B—C2B—C14B	−179.85 (17)	C6A—C1A—C2A—C14A	179.35 (17)
C1B—C2B—C3B—C4B	0.9 (3)	C1A—C2A—C3A—C4A	0.4 (3)
C14B—C2B—C3B—C4B	179.66 (17)	C14A—C2A—C3A—C4A	−179.57 (17)
C2B—C3B—C4B—C5B	0.0 (3)	C2A—C3A—C4A—C5A	0.4 (3)
C3B—C4B—C5B—F1B	179.21 (16)	C3A—C4A—C5A—F1A	178.27 (16)
C3B—C4B—C5B—C6B	−0.8 (3)	C3A—C4A—C5A—C6A	−1.0 (3)
F1B—C5B—C6B—C1B	−179.47 (16)	F1A—C5A—C6A—C1A	−178.49 (16)
C4B—C5B—C6B—C1B	0.6 (3)	C4A—C5A—C6A—C1A	0.8 (3)
N7B—C1B—C6B—C5B	−178.39 (18)	N7A—C1A—C6A—C5A	178.01 (18)
C2B—C1B—C6B—C5B	0.5 (3)	C2A—C1A—C6A—C5A	0.0 (3)
C6B—C1B—N7B—C8B	3.0 (3)	C6A—C1A—N7A—C8A	9.0 (3)
C2B—C1B—N7B—C8B	−175.79 (17)	C2A—C1A—N7A—C8A	−173.10 (18)
C1B—N7B—C8B—C13B	126.8 (2)	C1A—N7A—C8A—C9A	50.9 (3)
C1B—N7B—C8B—C9B	−54.3 (3)	C1A—N7A—C8A—C13A	−131.7 (2)
C13B—C8B—C9B—C10B	−2.5 (3)	C13A—C8A—C9A—C10A	1.4 (3)
N7B—C8B—C9B—C10B	178.62 (18)	N7A—C8A—C9A—C10A	178.73 (18)
C8B—C9B—C10B—C11B	1.9 (3)	C8A—C9A—C10A—C11A	−1.6 (3)
C9B—C10B—C11B—C12B	0.0 (3)	C9A—C10A—C11A—C12A	0.6 (3)
C10B—C11B—C12B—C13B	−1.3 (3)	C10A—C11A—C12A—C13A	0.6 (3)
C9B—C8B—C13B—C12B	1.3 (3)	C11A—C12A—C13A—C8A	−0.7 (3)
N7B—C8B—C13B—C12B	−179.79 (18)	C9A—C8A—C13A—C12A	−0.2 (3)
C11B—C12B—C13B—C8B	0.6 (3)	N7A—C8A—C13A—C12A	−177.65 (17)
C3B—C2B—C14B—O15B	−175.23 (18)	C3A—C2A—C14A—O15A	177.69 (18)
C1B—C2B—C14B—O15B	3.5 (3)	C1A—C2A—C14A—O15A	−2.2 (3)
C3B—C2B—C14B—O16B	4.6 (3)	C3A—C2A—C14A—O16A	−2.4 (3)
C1B—C2B—C14B—O16B	−176.67 (16)	C1A—C2A—C14A—O16A	177.70 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7A—H7A···O15A	0.88	1.98	2.673 (2)	135
N7B—H7B···O15B	0.88	1.98	2.6770 (19)	136
O16A—H16A···O15Bⁱ	0.84	1.80	2.6413 (19)	176
O16B—H16B···O15Aⁱ	0.84	1.77	2.6099 (19)	174
C4A—H4A···F1Bⁱⁱ	0.95	2.48	3.426 (2)	174
C4B—H4B···F1Aⁱⁱ	0.95	2.52	3.464 (2)	173

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

Funding information

JL and SL thank the Graduate Innovation Fund of WIT for financial support (CX2022066).

References

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