2-Fluoro-N-(2-fluoro-benzo-yl)-N-(2-pyrid-yl)benzamide.

The title compound, C(19)H(12)F(2)N(2)O(2), a 2:1 product of the reaction of 2-fluoro-benzoyl chloride and 2-amino-pyridine, crystallizes with a disordered 2-fluoro-benzene ring adopting two conformations [ratio of occupancies = 0.930 (4):0.070 (4)] in one of the two independent mol-ecules (differing slightly in conformation) comprising the asymmetric unit. In the crystal structure, C-H⋯O and C-H⋯π(arene) inter-actions are present.

Related literature

For background information, see: Donnelly et al. (2008 ▶); Gallagher et al. (2008 ▶, 2009 ▶); McMahon et al. (2008 ▶); Moody et al. (1998 ▶). For the parent compound, 2-(dibenzoyl­amino)­pyridine, see: Weng et al. (2006 ▶). For related structures, see: Akinboye, Butcher, Brandy et al. (2009 ▶); Akinboye, Butcher, Wright et al. (2009 ▶); Usman et al. (2002a ▶,b ▶).

Experimental

Crystal data

C19H12F2N2O2

M = 338.31

Monoclinic,

a = 8.7421 (3) Å

b = 20.4270 (8) Å

c = 17.8175 (5) Å

β = 104.145 (2)°

V = 3085.29 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 150 (1) K

0.30 × 0.14 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.850, T max = 0.988

7253 measured reflections

7044 independent reflections

3758 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.150

S = 0.99

7044 reflections

461 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.35 e Å−3

Data collection: KappaCCD Server Software (Nonius, 1997 ▶); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and SORTX (McArdle, 1995 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97 and PREP8 (Ferguson, 1998 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002189/tk2358sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002189/tk2358Isup2.hkl

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

C19H12F2N2O2	F(000) = 1392
Mr = 338.31	Dx = 1.457 Mg m−3
Monoclinic, P21/c	Melting point: 367 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.7421 (3) Å	Cell parameters from 8844 reflections
b = 20.4270 (8) Å	θ = 2.6–27.5°
c = 17.8175 (5) Å	µ = 0.11 mm−1
β = 104.145 (2)°	T = 150 K
V = 3085.29 (18) Å3	Block, colourless
Z = 8	0.30 × 0.14 × 0.12 mm

Nonius KappaCCD diffractometer	7044 independent reflections
Radiation source: fine-focus sealed X-ray tube	3758 reflections with I > 2σ(I)
graphite	Rint = 0.073
φ, and ω scans with κ offsets	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −11→10
Tmin = 0.850, Tmax = 0.988	k = −26→26
7253 measured reflections	l = −19→23

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0741P)2] where P = (Fo2 + 2Fc2)/3
7044 reflections	(Δ/σ)max < 0.001
461 parameters	Δρmax = 0.29 e Å−3
12 restraints	Δρmin = −0.35 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
F12A	0.92767 (18)	0.06141 (7)	0.57392 (7)	0.0448 (4)
O1A	0.9098 (2)	0.11920 (8)	0.36102 (9)	0.0388 (5)
C1A	0.8666 (3)	0.11698 (11)	0.42060 (12)	0.0275 (5)
N1A	0.8933 (2)	0.17057 (9)	0.47236 (10)	0.0253 (4)
C11A	0.7887 (3)	0.05768 (11)	0.44252 (12)	0.0258 (5)
C12A	0.8199 (3)	0.03140 (11)	0.51633 (13)	0.0297 (6)
C13A	0.7479 (3)	−0.02385 (12)	0.53475 (14)	0.0359 (6)
C14A	0.6365 (3)	−0.05401 (13)	0.47674 (17)	0.0418 (7)
C15A	0.6029 (3)	−0.03026 (13)	0.40146 (16)	0.0420 (7)
C16A	0.6804 (3)	0.02463 (12)	0.38468 (14)	0.0342 (6)
C21A	0.9919 (3)	0.22331 (11)	0.45829 (11)	0.0236 (5)
N22A	0.9235 (2)	0.28159 (9)	0.45101 (10)	0.0287 (5)
C23A	1.0123 (3)	0.33207 (12)	0.43746 (13)	0.0342 (6)
C24A	1.1639 (3)	0.32577 (13)	0.42965 (13)	0.0349 (6)
C25A	1.2317 (3)	0.26415 (13)	0.43804 (13)	0.0352 (6)
C26A	1.1448 (3)	0.21177 (12)	0.45259 (13)	0.0321 (6)
O2A	0.65467 (19)	0.16567 (8)	0.50477 (8)	0.0318 (4)
C2A	0.7900 (3)	0.18421 (11)	0.52090 (12)	0.0245 (5)
C31A	0.8623 (3)	0.21946 (11)	0.59384 (12)	0.0232 (5)
C32A	0.7764 (3)	0.26714 (11)	0.62237 (12)	0.0265 (5)
C33A	0.8292 (3)	0.29479 (11)	0.69417 (13)	0.0298 (6)
C34A	0.9731 (3)	0.27489 (12)	0.74019 (13)	0.0296 (6)
C35A	1.0635 (3)	0.22887 (11)	0.71327 (12)	0.0270 (5)
C36A	1.0083 (3)	0.20202 (11)	0.64032 (13)	0.0269 (5)
F32A	0.63827 (17)	0.28808 (7)	0.57553 (8)	0.0344 (5)	0.930 (4)
F36A	1.116 (2)	0.1620 (10)	0.6169 (10)	0.039 (7)	0.070 (4)
F12B	0.31068 (16)	0.18071 (7)	0.12221 (7)	0.0369 (4)
O1B	0.3159 (2)	0.12056 (8)	0.33481 (8)	0.0338 (4)
C1B	0.3604 (3)	0.12421 (11)	0.27555 (12)	0.0255 (5)
N1B	0.3322 (2)	0.07118 (9)	0.22248 (10)	0.0226 (4)
C11B	0.4330 (3)	0.18597 (11)	0.25606 (12)	0.0228 (5)
C12B	0.3982 (3)	0.21466 (11)	0.18366 (12)	0.0261 (5)
C13B	0.4425 (3)	0.27768 (12)	0.17050 (14)	0.0331 (6)
C14B	0.5283 (3)	0.31302 (12)	0.23274 (15)	0.0369 (6)
C15B	0.5697 (3)	0.28541 (12)	0.30609 (14)	0.0343 (6)
C16B	0.5208 (3)	0.22290 (12)	0.31764 (12)	0.0276 (6)
O2B	0.57182 (18)	0.07792 (8)	0.19299 (8)	0.0287 (4)
C2B	0.4384 (3)	0.05560 (11)	0.17782 (12)	0.0226 (5)
C21B	0.2073 (3)	0.02639 (11)	0.22749 (12)	0.0240 (5)
N22B	0.2476 (2)	−0.03583 (9)	0.23967 (10)	0.0266 (5)
C23B	0.1297 (3)	−0.07729 (12)	0.24352 (13)	0.0303 (6)
C24B	−0.0238 (3)	−0.05737 (12)	0.23712 (13)	0.0297 (6)
C25B	−0.0610 (3)	0.00756 (12)	0.22546 (13)	0.0313 (6)
C26B	0.0564 (3)	0.05108 (12)	0.21966 (13)	0.0282 (6)
F32B	0.59097 (16)	−0.05992 (7)	0.15023 (8)	0.0399 (4)
C31B	0.3775 (3)	0.01289 (11)	0.10932 (12)	0.0231 (5)
C32B	0.4601 (3)	−0.04192 (11)	0.09556 (13)	0.0268 (5)
C33B	0.4133 (3)	−0.07992 (12)	0.03030 (14)	0.0329 (6)
C34B	0.2801 (3)	−0.06149 (12)	−0.02500 (13)	0.0322 (6)
C35B	0.1943 (3)	−0.00704 (12)	−0.01392 (13)	0.0301 (6)
C36B	0.2418 (3)	0.02922 (12)	0.05330 (12)	0.0272 (5)
H13A	0.7738	−0.0409	0.5859	0.043*
H14A	0.5822	−0.0915	0.4884	0.050*
H15A	0.5271	−0.0517	0.3617	0.050*
H16A	0.6595	0.0401	0.3329	0.041*
H23A	0.9672	0.3746	0.4330	0.041*
H24A	1.2208	0.3627	0.4188	0.042*
H25A	1.3370	0.2582	0.4338	0.042*
H26A	1.1882	0.1689	0.4586	0.039*
H32A	0.6778	0.2809	0.5908	0.032*	0.070 (4)
H33A	0.7682	0.3270	0.7120	0.036*
H34A	1.0101	0.2929	0.7905	0.036*
H35A	1.1628	0.2158	0.7448	0.032*
H36A	1.0716	0.1711	0.6218	0.032*	0.930 (4)
H13B	0.4148	0.2962	0.1201	0.040*
H14B	0.5593	0.3566	0.2253	0.044*
H15B	0.6316	0.3096	0.3483	0.041*
H16B	0.5472	0.2047	0.3682	0.033*
H23B	0.1536	−0.1226	0.2510	0.036*
H24B	−0.1027	−0.0883	0.2408	0.036*
H25B	−0.1657	0.0224	0.2214	0.038*
H26B	0.0347	0.0964	0.2106	0.034*
H33B	0.4711	−0.1179	0.0234	0.039*
H34B	0.2472	−0.0865	−0.0711	0.039*
H35B	0.1030	0.0054	−0.0523	0.036*
H36B	0.1809	0.0659	0.0614	0.033*

	U11	U22	U33	U12	U13	U23
F12A	0.0657 (11)	0.0363 (9)	0.0259 (7)	−0.0103 (8)	−0.0013 (7)	0.0017 (6)
O1A	0.0593 (13)	0.0352 (11)	0.0259 (9)	−0.0102 (9)	0.0179 (8)	−0.0037 (8)
C1A	0.0307 (14)	0.0275 (14)	0.0235 (12)	−0.0019 (11)	0.0050 (10)	0.0008 (10)
N1A	0.0333 (12)	0.0219 (11)	0.0227 (10)	−0.0053 (9)	0.0106 (8)	−0.0023 (8)
C11A	0.0302 (14)	0.0217 (13)	0.0266 (12)	−0.0002 (11)	0.0089 (10)	−0.0014 (10)
C12A	0.0373 (15)	0.0245 (14)	0.0269 (12)	−0.0012 (12)	0.0074 (11)	−0.0011 (10)
C13A	0.0472 (17)	0.0249 (14)	0.0397 (14)	0.0030 (13)	0.0186 (13)	0.0065 (11)
C14A	0.0358 (16)	0.0250 (15)	0.0669 (19)	−0.0029 (12)	0.0169 (14)	0.0046 (13)
C15A	0.0334 (16)	0.0279 (16)	0.0592 (18)	−0.0049 (12)	0.0006 (13)	−0.0053 (13)
C16A	0.0368 (15)	0.0296 (15)	0.0324 (13)	0.0016 (12)	0.0009 (11)	−0.0026 (11)
C21A	0.0315 (14)	0.0205 (13)	0.0194 (11)	−0.0035 (11)	0.0071 (10)	−0.0006 (9)
N22A	0.0347 (12)	0.0244 (12)	0.0278 (10)	−0.0027 (9)	0.0092 (9)	0.0010 (8)
C23A	0.0446 (17)	0.0252 (14)	0.0323 (13)	−0.0037 (12)	0.0084 (11)	0.0034 (11)
C24A	0.0375 (16)	0.0368 (17)	0.0309 (13)	−0.0140 (13)	0.0095 (11)	−0.0027 (11)
C25A	0.0318 (15)	0.0418 (17)	0.0349 (14)	−0.0049 (13)	0.0137 (11)	−0.0055 (12)
C26A	0.0338 (15)	0.0306 (15)	0.0330 (13)	0.0002 (12)	0.0103 (11)	−0.0019 (11)
O2A	0.0271 (10)	0.0336 (10)	0.0347 (9)	−0.0057 (8)	0.0073 (7)	−0.0030 (7)
C2A	0.0285 (14)	0.0199 (13)	0.0254 (12)	0.0004 (11)	0.0074 (10)	0.0025 (9)
C31A	0.0254 (13)	0.0214 (13)	0.0252 (11)	−0.0034 (10)	0.0107 (10)	0.0006 (9)
C32A	0.0248 (13)	0.0260 (14)	0.0289 (12)	−0.0008 (11)	0.0070 (10)	0.0041 (10)
C33A	0.0383 (16)	0.0238 (14)	0.0308 (13)	0.0015 (11)	0.0148 (11)	−0.0040 (10)
C34A	0.0370 (15)	0.0306 (15)	0.0232 (12)	−0.0077 (12)	0.0109 (11)	−0.0041 (10)
C35A	0.0279 (14)	0.0279 (14)	0.0249 (12)	−0.0020 (11)	0.0056 (10)	−0.0006 (10)
C36A	0.0297 (14)	0.0236 (13)	0.0305 (12)	−0.0014 (11)	0.0134 (11)	−0.0013 (10)
F32A	0.0323 (10)	0.0337 (10)	0.0364 (9)	0.0058 (7)	0.0067 (7)	0.0020 (7)
F36A	0.049 (10)	0.041 (10)	0.028 (9)	0.007 (7)	0.009 (7)	−0.010 (7)
F12B	0.0475 (9)	0.0340 (9)	0.0248 (7)	−0.0040 (7)	0.0002 (6)	0.0016 (6)
O1B	0.0453 (11)	0.0324 (10)	0.0273 (9)	−0.0073 (8)	0.0159 (8)	−0.0026 (7)
C1B	0.0245 (13)	0.0264 (14)	0.0246 (12)	0.0022 (11)	0.0040 (10)	−0.0003 (10)
N1B	0.0238 (11)	0.0220 (11)	0.0236 (10)	−0.0032 (8)	0.0087 (8)	−0.0031 (8)
C11B	0.0220 (12)	0.0199 (13)	0.0272 (12)	0.0028 (10)	0.0073 (10)	−0.0008 (10)
C12B	0.0262 (14)	0.0254 (14)	0.0259 (12)	−0.0004 (10)	0.0048 (10)	−0.0012 (10)
C13B	0.0346 (15)	0.0286 (15)	0.0373 (14)	0.0027 (12)	0.0112 (12)	0.0057 (11)
C14B	0.0344 (16)	0.0231 (15)	0.0543 (17)	−0.0028 (12)	0.0130 (13)	0.0028 (12)
C15B	0.0288 (15)	0.0289 (15)	0.0428 (15)	−0.0039 (11)	0.0043 (11)	−0.0089 (11)
C16B	0.0258 (13)	0.0291 (14)	0.0267 (12)	0.0024 (11)	0.0041 (10)	−0.0017 (10)
O2B	0.0230 (10)	0.0303 (10)	0.0324 (9)	−0.0024 (8)	0.0061 (7)	−0.0030 (7)
C2B	0.0226 (13)	0.0181 (12)	0.0266 (12)	0.0027 (10)	0.0051 (10)	0.0035 (9)
C21B	0.0282 (14)	0.0243 (14)	0.0205 (11)	−0.0017 (11)	0.0081 (9)	−0.0014 (9)
N22B	0.0271 (11)	0.0230 (12)	0.0300 (10)	−0.0004 (9)	0.0076 (8)	0.0016 (8)
C23B	0.0314 (15)	0.0214 (13)	0.0385 (14)	−0.0021 (11)	0.0093 (11)	0.0051 (11)
C24B	0.0265 (14)	0.0324 (15)	0.0302 (13)	−0.0038 (11)	0.0066 (10)	0.0026 (11)
C25B	0.0247 (14)	0.0377 (16)	0.0320 (13)	0.0000 (12)	0.0077 (10)	−0.0031 (11)
C26B	0.0269 (14)	0.0223 (13)	0.0350 (13)	0.0041 (11)	0.0069 (10)	−0.0016 (10)
F32B	0.0325 (8)	0.0372 (9)	0.0440 (8)	0.0094 (7)	−0.0021 (7)	−0.0055 (7)
C31B	0.0249 (13)	0.0213 (13)	0.0247 (11)	−0.0005 (10)	0.0092 (10)	0.0012 (9)
C32B	0.0214 (13)	0.0289 (14)	0.0294 (12)	−0.0007 (11)	0.0050 (10)	0.0001 (10)
C33B	0.0351 (16)	0.0282 (14)	0.0369 (14)	0.0022 (12)	0.0117 (12)	−0.0081 (11)
C34B	0.0336 (15)	0.0353 (16)	0.0276 (13)	−0.0044 (12)	0.0076 (11)	−0.0082 (11)
C35B	0.0271 (14)	0.0335 (15)	0.0273 (12)	−0.0007 (12)	0.0020 (10)	0.0016 (11)
C36B	0.0239 (13)	0.0298 (14)	0.0282 (12)	0.0026 (11)	0.0070 (10)	−0.0006 (10)

F12A—C12A	1.358 (3)	F12B—C12B	1.362 (2)
O1A—C1A	1.211 (2)	O1B—C1B	1.214 (2)
C1A—N1A	1.414 (3)	C1B—N1B	1.419 (3)
C1A—C11A	1.488 (3)	C1B—C11B	1.491 (3)
N1A—C2A	1.422 (3)	N1B—C2B	1.399 (3)
N1A—C21A	1.439 (3)	N1B—C21B	1.444 (3)
C11A—C12A	1.385 (3)	C11B—C12B	1.381 (3)
C11A—C16A	1.392 (3)	C11B—C16B	1.397 (3)
C12A—C13A	1.371 (3)	C12B—C13B	1.381 (3)
C13A—C14A	1.380 (4)	C13B—C14B	1.381 (3)
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—C15A	1.389 (4)	C14B—C15B	1.388 (3)
C14A—H14A	0.9500	C14B—H14B	0.9500
C15A—C16A	1.380 (3)	C15B—C16B	1.378 (3)
C15A—H15A	0.9500	C15B—H15B	0.9500
C16A—H16A	0.9500	C16B—H16B	0.9500
O2A—C2A	1.208 (3)	O2B—C2B	1.220 (3)
C2A—C31A	1.485 (3)	C2B—C31B	1.489 (3)
C21A—N22A	1.324 (3)	C21B—N22B	1.323 (3)
C21A—C26A	1.385 (3)	C21B—C26B	1.387 (3)
N22A—C23A	1.348 (3)	N22B—C23B	1.349 (3)
C23A—C24A	1.372 (4)	C23B—C24B	1.380 (3)
C23A—H23A	0.9500	C23B—H23B	0.9500
C24A—C25A	1.384 (3)	C24B—C25B	1.369 (3)
C24A—H24A	0.9500	C24B—H24B	0.9500
C25A—C26A	1.373 (3)	C25B—C26B	1.381 (3)
C25A—H25A	0.9500	C25B—H25B	0.9500
C26A—H26A	0.9500	C26B—H26B	0.9500
C31A—C36A	1.388 (3)	F32B—C32B	1.360 (3)
C31A—C32A	1.399 (3)	C31B—C32B	1.386 (3)
C32A—C33A	1.371 (3)	C31B—C36B	1.391 (3)
C32A—H32A	0.9500	C32B—C33B	1.374 (3)
C33A—C34A	1.384 (3)	C33B—C34B	1.381 (3)
C33A—H33A	0.9500	C33B—H33B	0.9500
C34A—C35A	1.387 (3)	C34B—C35B	1.383 (3)
C34A—H34A	0.9500	C34B—H34B	0.9500
C35A—C36A	1.384 (3)	C35B—C36B	1.383 (3)
C35A—H35A	0.9500	C35B—H35B	0.9500
C36A—H36A	0.9500	C36B—H36B	0.9500
O1A—C1A—N1A	120.4 (2)	O1B—C1B—N1B	119.5 (2)
O1A—C1A—C11A	121.4 (2)	O1B—C1B—C11B	119.99 (19)
N1A—C1A—C11A	118.18 (18)	N1B—C1B—C11B	120.36 (18)
C1A—N1A—C2A	121.35 (18)	C2B—N1B—C1B	121.40 (18)
C1A—N1A—C21A	118.44 (16)	C2B—N1B—C21B	120.51 (17)
C2A—N1A—C21A	117.10 (17)	C1B—N1B—C21B	116.97 (16)
C12A—C11A—C16A	117.1 (2)	C12B—C11B—C16B	117.3 (2)
C12A—C11A—C1A	124.6 (2)	C12B—C11B—C1B	124.6 (2)
C16A—C11A—C1A	118.2 (2)	C16B—C11B—C1B	117.23 (19)
F12A—C12A—C13A	117.7 (2)	F12B—C12B—C13B	117.6 (2)
F12A—C12A—C11A	118.8 (2)	F12B—C12B—C11B	119.1 (2)
C13A—C12A—C11A	123.4 (2)	C13B—C12B—C11B	123.2 (2)
C12A—C13A—C14A	118.0 (2)	C14B—C13B—C12B	118.1 (2)
C12A—C13A—H13A	121.0	C14B—C13B—H13B	121.0
C14A—C13A—H13A	121.0	C12B—C13B—H13B	121.0
C13A—C14A—C15A	120.8 (2)	C13B—C14B—C15B	120.6 (2)
C13A—C14A—H14A	119.6	C13B—C14B—H14B	119.7
C15A—C14A—H14A	119.6	C15B—C14B—H14B	119.7
C16A—C15A—C14A	119.6 (2)	C16B—C15B—C14B	119.9 (2)
C16A—C15A—H15A	120.2	C16B—C15B—H15B	120.1
C14A—C15A—H15A	120.2	C14B—C15B—H15B	120.1
C15A—C16A—C11A	121.0 (2)	C15B—C16B—C11B	120.9 (2)
C15A—C16A—H16A	119.5	C15B—C16B—H16B	119.5
C11A—C16A—H16A	119.5	C11B—C16B—H16B	119.5
N22A—C21A—C26A	124.5 (2)	O2B—C2B—N1B	121.36 (19)
N22A—C21A—N1A	114.50 (19)	O2B—C2B—C31B	122.12 (19)
C26A—C21A—N1A	121.0 (2)	N1B—C2B—C31B	116.47 (19)
C21A—N22A—C23A	116.1 (2)	N22B—C21B—C26B	125.1 (2)
N22A—C23A—C24A	124.0 (2)	N22B—C21B—N1B	116.36 (19)
N22A—C23A—H23A	118.0	C26B—C21B—N1B	118.6 (2)
C24A—C23A—H23A	118.0	C21B—N22B—C23B	115.8 (2)
C23A—C24A—C25A	118.3 (2)	N22B—C23B—C24B	123.4 (2)
C23A—C24A—H24A	120.9	N22B—C23B—H23B	118.3
C25A—C24A—H24A	120.9	C24B—C23B—H23B	118.3
C26A—C25A—C24A	119.1 (2)	C25B—C24B—C23B	119.2 (2)
C26A—C25A—H25A	120.4	C25B—C24B—H24B	120.4
C24A—C25A—H25A	120.4	C23B—C24B—H24B	120.4
C25A—C26A—C21A	118.0 (2)	C24B—C25B—C26B	118.8 (2)
C25A—C26A—H26A	121.0	C24B—C25B—H25B	120.6
C21A—C26A—H26A	121.0	C26B—C25B—H25B	120.6
O2A—C2A—N1A	121.6 (2)	C25B—C26B—C21B	117.7 (2)
O2A—C2A—C31A	122.89 (19)	C25B—C26B—H26B	121.2
N1A—C2A—C31A	115.42 (19)	C21B—C26B—H26B	121.2
C36A—C31A—C32A	117.3 (2)	C32B—C31B—C36B	117.2 (2)
C36A—C31A—C2A	122.0 (2)	C32B—C31B—C2B	121.4 (2)
C32A—C31A—C2A	120.3 (2)	C36B—C31B—C2B	121.3 (2)
C33A—C32A—C31A	122.5 (2)	F32B—C32B—C33B	118.5 (2)
C33A—C32A—H32A	118.7	F32B—C32B—C31B	118.4 (2)
C31A—C32A—H32A	118.7	C33B—C32B—C31B	123.1 (2)
C32A—C33A—C34A	118.8 (2)	C32B—C33B—C34B	118.3 (2)
C32A—C33A—H33A	120.6	C32B—C33B—H33B	120.8
C34A—C33A—H33A	120.6	C34B—C33B—H33B	120.8
C33A—C34A—C35A	120.4 (2)	C33B—C34B—C35B	120.6 (2)
C33A—C34A—H34A	119.8	C33B—C34B—H34B	119.7
C35A—C34A—H34A	119.8	C35B—C34B—H34B	119.7
C36A—C35A—C34A	119.8 (2)	C34B—C35B—C36B	119.7 (2)
C36A—C35A—H35A	120.1	C34B—C35B—H35B	120.1
C34A—C35A—H35A	120.1	C36B—C35B—H35B	120.1
C35A—C36A—C31A	121.1 (2)	C35B—C36B—C31B	121.1 (2)
C35A—C36A—H36A	119.4	C35B—C36B—H36B	119.5
C31A—C36A—H36A	119.4	C31B—C36B—H36B	119.5
O1A—C1A—N1A—C2A	150.7 (2)	O1B—C1B—N1B—C21B	21.0 (3)
C11A—C1A—N1A—C2A	−31.0 (3)	C11B—C1B—N1B—C21B	−154.2 (2)
O1A—C1A—N1A—C21A	−8.8 (3)	O1B—C1B—C11B—C12B	−135.7 (2)
C11A—C1A—N1A—C21A	169.5 (2)	N1B—C1B—C11B—C12B	39.5 (3)
O1A—C1A—C11A—C12A	137.7 (2)	O1B—C1B—C11B—C16B	32.8 (3)
N1A—C1A—C11A—C12A	−40.6 (3)	N1B—C1B—C11B—C16B	−152.0 (2)
O1A—C1A—C11A—C16A	−40.0 (3)	C16B—C11B—C12B—F12B	−178.99 (18)
N1A—C1A—C11A—C16A	141.7 (2)	C1B—C11B—C12B—F12B	−10.5 (3)
C16A—C11A—C12A—F12A	178.5 (2)	C16B—C11B—C12B—C13B	−1.7 (3)
C1A—C11A—C12A—F12A	0.8 (3)	C1B—C11B—C12B—C13B	166.9 (2)
C16A—C11A—C12A—C13A	−1.4 (4)	F12B—C12B—C13B—C14B	178.6 (2)
C1A—C11A—C12A—C13A	−179.1 (2)	C11B—C12B—C13B—C14B	1.2 (4)
F12A—C12A—C13A—C14A	179.0 (2)	C12B—C13B—C14B—C15B	0.7 (4)
C11A—C12A—C13A—C14A	−1.1 (4)	C13B—C14B—C15B—C16B	−2.0 (4)
C12A—C13A—C14A—C15A	2.2 (4)	C14B—C15B—C16B—C11B	1.6 (4)
C13A—C14A—C15A—C16A	−0.8 (4)	C12B—C11B—C16B—C15B	0.2 (3)
C14A—C15A—C16A—C11A	−1.8 (4)	C1B—C11B—C16B—C15B	−169.2 (2)
C12A—C11A—C16A—C15A	2.8 (4)	C1B—N1B—C2B—O2B	14.6 (3)
C1A—C11A—C16A—C15A	−179.3 (2)	C21B—N1B—C2B—O2B	−153.0 (2)
C1A—N1A—C21A—N22A	123.0 (2)	C1B—N1B—C2B—C31B	−162.91 (19)
C2A—N1A—C21A—N22A	−37.3 (3)	C21B—N1B—C2B—C31B	29.5 (3)
C1A—N1A—C21A—C26A	−56.5 (3)	C2B—N1B—C21B—N22B	45.8 (3)
C2A—N1A—C21A—C26A	143.2 (2)	C1B—N1B—C21B—N22B	−122.3 (2)
C26A—C21A—N22A—C23A	−0.3 (3)	C2B—N1B—C21B—C26B	−134.4 (2)
N1A—C21A—N22A—C23A	−179.74 (18)	C1B—N1B—C21B—C26B	57.5 (3)
C21A—N22A—C23A—C24A	1.3 (3)	C26B—C21B—N22B—C23B	0.9 (3)
N22A—C23A—C24A—C25A	−1.7 (4)	N1B—C21B—N22B—C23B	−179.40 (18)
C23A—C24A—C25A—C26A	1.0 (3)	C21B—N22B—C23B—C24B	−1.4 (3)
C24A—C25A—C26A—C21A	−0.1 (3)	N22B—C23B—C24B—C25B	0.7 (3)
N22A—C21A—C26A—C25A	−0.3 (3)	C23B—C24B—C25B—C26B	0.7 (3)
N1A—C21A—C26A—C25A	179.12 (19)	C24B—C25B—C26B—C21B	−1.2 (3)
C1A—N1A—C2A—O2A	−23.5 (3)	N22B—C21B—C26B—C25B	0.4 (3)
C21A—N1A—C2A—O2A	136.3 (2)	N1B—C21B—C26B—C25B	−179.31 (18)
C1A—N1A—C2A—C31A	153.5 (2)	O2B—C2B—C31B—C32B	51.8 (3)
C21A—N1A—C2A—C31A	−46.8 (3)	N1B—C2B—C31B—C32B	−130.8 (2)
O2A—C2A—C31A—C36A	132.2 (2)	O2B—C2B—C31B—C36B	−123.1 (2)
N1A—C2A—C31A—C36A	−44.8 (3)	N1B—C2B—C31B—C36B	54.4 (3)
O2A—C2A—C31A—C32A	−40.7 (3)	C36B—C31B—C32B—F32B	−178.40 (19)
N1A—C2A—C31A—C32A	142.4 (2)	C2B—C31B—C32B—F32B	6.5 (3)
C36A—C31A—C32A—C33A	−2.1 (3)	C36B—C31B—C32B—C33B	−0.3 (3)
C2A—C31A—C32A—C33A	171.1 (2)	C2B—C31B—C32B—C33B	−175.4 (2)
C31A—C32A—C33A—C34A	0.1 (3)	F32B—C32B—C33B—C34B	179.9 (2)
C32A—C33A—C34A—C35A	1.4 (3)	C31B—C32B—C33B—C34B	1.8 (4)
C33A—C34A—C35A—C36A	−0.9 (3)	C32B—C33B—C34B—C35B	−1.5 (4)
C34A—C35A—C36A—C31A	−1.2 (3)	C33B—C34B—C35B—C36B	−0.2 (4)
C32A—C31A—C36A—C35A	2.6 (3)	C34B—C35B—C36B—C31B	1.8 (3)
C2A—C31A—C36A—C35A	−170.4 (2)	C32B—C31B—C36B—C35B	−1.5 (3)
O1B—C1B—N1B—C2B	−147.0 (2)	C2B—C31B—C36B—C35B	173.6 (2)
C11B—C1B—N1B—C2B	37.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13A—H13A···O1Bi	0.95	2.41	3.201 (3)	141
C14A—H14A···O2Ai	0.95	2.59	3.493 (3)	158
C16A—H16A···O2B	0.95	2.54	3.488 (3)	174
C33A—H33A···O2Bii	0.95	2.56	3.435 (3)	154
C34A—H34A···O1Aii	0.95	2.47	3.194 (3)	133
C35A—H35A···Cg1iii	0.95	2.88	3.591 (3)	133
C16B—H16B···O2A	0.95	2.51	3.456 (3)	172
C25B—H25B···O2Biv	0.95	2.50	3.434 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13A—H13A⋯O1Bi	0.95	2.41	3.201 (3)	141
C14A—H14A⋯O2Ai	0.95	2.59	3.493 (3)	158
C16A—H16A⋯O2B	0.95	2.54	3.488 (3)	174
C33A—H33A⋯O2Bii	0.95	2.56	3.435 (3)	154
C34A—H34A⋯O1Aii	0.95	2.47	3.194 (3)	133
C35A—H35A⋯Cg1iii	0.95	2.88	3.591 (3)	133
C16B—H16B⋯O2A	0.95	2.51	3.456 (3)	172
C25B—H25B⋯O2Biv	0.95	2.50	3.434 (3)	169

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C11–C16 benzene ring.