Structural systematics and conformational analyses of a 3 × 3 isomer grid of fluoro-N-(pyridyl)benz­amides: physicochemical correlations, polymorphism and isomorphous relationships

An isomer grid of nine fluoro-N-(pyridyl)benzamides (Fxx) (x = para-/meta-/ortho-) has been examined to correlate structural relationships between the experimental crystal structure and ab initio calculations, based on the effect of fluorine (Fx) and pyridine N-atom (x) substitution patterns on molecular conformation. Eight isomers form N—H...N hydrogen bonds, and only one (Fom) aggregates via intermolecular N—H...O=C interactions exclusively. The Fpm and Fom isomers both crystallize as two polymorphs with Fpm_O (N—H...O=C chains, P-syn) and Fpm_N (N—H...N chains, P-anti) both in P2₁/n (Z′ = 1) differing by their meta-N atom locations (P-syn, P-anti; N_pyridine referenced to N—H), whereas the disordered Fom_O is mostly P-syn (Z′ = 6) compared with Fom_F (P-anti) (Z′ = 1). In the Fxo triad twisted dimers form cyclic R²₂(8) rings via N—H...N interactions. Computational modelling and conformational preferences of the isomer grid demonstrate that the solid-state conformations generally conform with the most stable calculated conformations except for the Fxm triad, while calculations of the Fox triad predict the intramolecular N—H...F interaction established by spectroscopic and crystallographic data. Comparisons of Fxx with related isomer grids reveal a high degree of similarity in solid-state aggregation and physicochemical properties, while correlation of the melting point behaviour indicates the significance of the substituent position on melting point behaviour rather than the nature of the substituent.

S1. Comment

From the condensation reactions we crystallized six isomeric benzamides to give eight distict structures. In addition we obtained the room temperature structures for the Fxp triad which have already been published but at low temperature.

Related literature

For background information from our group, see: Donnelly et al., 2008. Gallagher et al., (2009a,b). McMahon et al., 2008. Mocilac et al., 2010, 2011. Mocilac & Gallagher, 2011.

S2. Experimental

Compounds (I) to (IX) or named as (Fpp) to (Foo).

S3. Refinement

H atoms attached to C atoms were treated as riding using the SHELXL97 (Sheldrick, 2008) defaults at 150 (1) K with C—H = 0.95 Å (aromatic) and U_iso(H) = 1.2U_eq(C) (aromatic).

The N—H H atoms were refined with isotropic displacement parameters unless in disordered systems whereby the N—H was treated as a riding atom.

Computing details

For all compounds, data collection: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46); cell refinement: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46); data reduction: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46); 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, 2009); software used to prepare material for publication: SHELXL97.

Figures

Figures 1–5. A view of (I) to (IX) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. ORTEP diagrams of the molecular structures of some of the nine isomers from Fpp to Foo.

(Fpp-10-124) 4-Fluoro-N-(pyridin-4-yl)benzamide

Crystal data

C12H9FN2O	F(000) = 448
Mr = 216.21	Dx = 1.427 Mg m^−3
Monoclinic, P21/c	Melting point: 461 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.6777 (1) Å	Cell parameters from 5255 reflections
b = 11.4769 (2) Å	θ = 2.6–27.5°
c = 15.5289 (3) Å	µ = 0.11 mm^−1
β = 95.974 (2)°	T = 294 K
V = 1006.40 (3) Å^3	Block, colourless
Z = 4	0.39 × 0.25 × 0.19 mm

Data collection

Xcalibur, Sapphire3, Gemini Ultra diffractometer	1979 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.013
Graphite monochromator	θmax = 27.8°, θmin = 2.6°
ω scans	h = −7→7
Absorption correction: analytical (ABSFAC, Clark and Reid, 1998)	k = −15→14
Tmin = 0.960, Tmax = 0.980	l = −19→19
7351 measured reflections	7599 standard reflections every 60 min
2216 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.0388P)^2 + 0.2424P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2216 reflections	Δρmax = 0.20 e Å^−3
150 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (3)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F14	0.87229 (18)	0.45954 (8)	0.64358 (6)	0.0755 (3)
O1	1.09479 (15)	0.04913 (8)	0.40012 (6)	0.0476 (2)
C1	0.9023 (2)	0.09065 (10)	0.41083 (7)	0.0341 (2)
N1	0.69275 (19)	0.05257 (9)	0.36941 (7)	0.0412 (3)
H1	0.580 (3)	0.1009 (14)	0.3682 (10)	0.056 (4)*
C11	0.88200 (19)	0.19020 (9)	0.47152 (7)	0.0329 (2)
C12	1.0667 (2)	0.26980 (10)	0.48104 (7)	0.0374 (3)
H12	1.1945	0.2612	0.4486	0.045*
C13	1.0623 (2)	0.36165 (11)	0.53823 (8)	0.0441 (3)
H13	1.1841	0.4161	0.5442	0.053*
C14	0.8731 (2)	0.37027 (11)	0.58611 (8)	0.0470 (3)
C15	0.6888 (2)	0.29287 (12)	0.57928 (8)	0.0476 (3)
H15	0.5641	0.3011	0.6132	0.057*
C16	0.6921 (2)	0.20211 (11)	0.52079 (8)	0.0400 (3)
H16	0.5676	0.1491	0.5144	0.048*
C21	0.6588 (2)	−0.04089 (10)	0.31169 (7)	0.0341 (3)
C22	0.4453 (2)	−0.04844 (11)	0.25949 (8)	0.0421 (3)
H22	0.3285	0.0077	0.2630	0.051*
C23	0.4089 (2)	−0.13984 (12)	0.20268 (9)	0.0468 (3)
H23	0.2654	−0.1429	0.1679	0.056*
N24	0.56608 (19)	−0.22482 (9)	0.19388 (7)	0.0445 (3)
C25	0.7683 (2)	−0.21652 (10)	0.24539 (8)	0.0409 (3)
H25	0.8806	−0.2747	0.2412	0.049*
C26	0.8241 (2)	−0.12859 (10)	0.30433 (7)	0.0378 (3)
H26	0.9689	−0.1279	0.3384	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F14	0.0856 (7)	0.0658 (6)	0.0754 (6)	0.0075 (5)	0.0098 (5)	−0.0398 (5)
O1	0.0405 (5)	0.0442 (5)	0.0590 (6)	0.0031 (4)	0.0094 (4)	−0.0136 (4)
C1	0.0400 (6)	0.0309 (5)	0.0313 (5)	0.0040 (4)	0.0031 (4)	0.0010 (4)
N1	0.0406 (5)	0.0393 (5)	0.0417 (5)	0.0114 (4)	−0.0049 (4)	−0.0106 (4)
C11	0.0366 (5)	0.0327 (5)	0.0283 (5)	0.0071 (4)	−0.0018 (4)	0.0011 (4)
C12	0.0393 (6)	0.0374 (6)	0.0354 (6)	0.0046 (5)	0.0031 (4)	0.0011 (5)
C13	0.0469 (7)	0.0360 (6)	0.0478 (7)	0.0009 (5)	−0.0024 (5)	−0.0036 (5)
C14	0.0555 (7)	0.0427 (7)	0.0415 (7)	0.0134 (6)	−0.0022 (5)	−0.0127 (5)
C15	0.0433 (7)	0.0573 (8)	0.0429 (7)	0.0133 (6)	0.0073 (5)	−0.0074 (6)
C16	0.0368 (6)	0.0433 (6)	0.0392 (6)	0.0044 (5)	0.0014 (5)	−0.0017 (5)
C21	0.0394 (6)	0.0330 (6)	0.0299 (5)	0.0005 (4)	0.0040 (4)	−0.0011 (4)
C22	0.0356 (6)	0.0439 (7)	0.0466 (7)	0.0039 (5)	0.0031 (5)	−0.0073 (5)
C23	0.0374 (6)	0.0531 (8)	0.0487 (7)	−0.0034 (5)	−0.0012 (5)	−0.0114 (6)
N24	0.0457 (6)	0.0424 (6)	0.0454 (6)	−0.0046 (4)	0.0048 (4)	−0.0113 (5)
C25	0.0457 (6)	0.0337 (6)	0.0436 (6)	0.0030 (5)	0.0057 (5)	−0.0035 (5)
C26	0.0410 (6)	0.0352 (6)	0.0361 (6)	0.0043 (5)	−0.0014 (5)	−0.0006 (5)

Geometric parameters (Å, º)

F14—C14	1.3591 (14)	C15—C16	1.3835 (17)
O1—C1	1.2195 (14)	C15—H15	0.9300
C1—N1	1.3641 (15)	C16—H16	0.9300
C1—C11	1.4931 (15)	C21—C26	1.3888 (16)
N1—C21	1.3983 (14)	C21—C22	1.3894 (16)
N1—H1	0.848 (16)	C22—C23	1.3724 (17)
C11—C12	1.3871 (16)	C22—H22	0.9300
C11—C16	1.3921 (16)	C23—N24	1.3386 (16)
C12—C13	1.3803 (16)	C23—H23	0.9300
C12—H12	0.9300	N24—C25	1.3327 (16)
C13—C14	1.3722 (19)	C25—C26	1.3770 (16)
C13—H13	0.9300	C25—H25	0.9300
C14—C15	1.368 (2)	C26—H26	0.9300
O1—C1—N1	124.09 (11)	C16—C15—H15	120.8
O1—C1—C11	120.94 (10)	C15—C16—C11	119.94 (11)
N1—C1—C11	114.96 (9)	C15—C16—H16	120.0
C1—N1—C21	127.10 (10)	C11—C16—H16	120.0
C1—N1—H1	115.0 (11)	C26—C21—C22	117.58 (10)
C21—N1—H1	115.7 (11)	C26—C21—N1	124.03 (10)
C12—C11—C16	119.80 (10)	C22—C21—N1	118.38 (10)
C12—C11—C1	117.65 (10)	C23—C22—C21	119.10 (11)
C16—C11—C1	122.48 (10)	C23—C22—H22	120.4
C13—C12—C11	120.49 (11)	C21—C22—H22	120.4
C13—C12—H12	119.8	N24—C23—C22	124.42 (11)
C11—C12—H12	119.8	N24—C23—H23	117.8
C14—C13—C12	118.12 (12)	C22—C23—H23	117.8
C14—C13—H13	120.9	C25—N24—C23	115.38 (10)
C12—C13—H13	120.9	N24—C25—C26	125.13 (11)
F14—C14—C15	119.05 (12)	N24—C25—H25	117.4
F14—C14—C13	117.80 (13)	C26—C25—H25	117.4
C15—C14—C13	123.14 (11)	C25—C26—C21	118.37 (11)
C14—C15—C16	118.49 (11)	C25—C26—H26	120.8
C14—C15—H15	120.8	C21—C26—H26	120.8
O1—C1—N1—C21	2.8 (2)	C14—C15—C16—C11	0.96 (18)
C11—C1—N1—C21	−177.77 (10)	C12—C11—C16—C15	−0.28 (17)
O1—C1—C11—C12	31.87 (16)	C1—C11—C16—C15	176.64 (11)
N1—C1—C11—C12	−147.60 (11)	C1—N1—C21—C26	17.61 (19)
O1—C1—C11—C16	−145.11 (12)	C1—N1—C21—C22	−163.76 (12)
N1—C1—C11—C16	35.41 (15)	C26—C21—C22—C23	−1.08 (18)
C16—C11—C12—C13	−0.82 (17)	N1—C21—C22—C23	−179.80 (11)
C1—C11—C12—C13	−177.89 (10)	C21—C22—C23—N24	0.6 (2)
C11—C12—C13—C14	1.20 (18)	C22—C23—N24—C25	0.27 (19)
C12—C13—C14—F14	178.68 (11)	C23—N24—C25—C26	−0.59 (18)
C12—C13—C14—C15	−0.5 (2)	N24—C25—C26—C21	0.06 (19)
F14—C14—C15—C16	−179.75 (11)	C22—C21—C26—C25	0.79 (17)
C13—C14—C15—C16	−0.6 (2)	N1—C21—C26—C25	179.43 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N24^i	0.848 (16)	2.335 (17)	3.0581 (15)	143.5 (14)
C26—H26···O1	0.93	2.33	2.8738 (15)	117
C26—H26···Cg1^ii	0.93	2.77	3.4183 (12)	127

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+2, −y, −z+1.

(Fmp-10-126) 3-Fluoro-N-(pyridin-4-yl)benzamide

Crystal data

C12H9FN2O	F(000) = 448
Mr = 216.21	Dx = 1.442 Mg m^−3
Monoclinic, P21/c	Melting point: 460 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.7961 (1) Å	Cell parameters from 5573 reflections
b = 11.3050 (2) Å	θ = 2.6–27.5°
c = 15.2384 (2) Å	µ = 0.11 mm^−1
β = 94.238 (1)°	T = 294 K
V = 995.76 (3) Å^3	Block, colourless
Z = 4	0.37 × 0.34 × 0.19 mm

Data collection

Xcalibur, Sapphire3, Gemini Ultra diffractometer	1988 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.012
Graphite monochromator	θmax = 27.8°, θmin = 2.7°
ω scans	h = −7→7
Absorption correction: analytical (ABSFAC, Clark and Reid, 1998)	k = −14→14
Tmin = 0.961, Tmax = 0.980	l = −19→15
7728 measured reflections	7983 standard reflections every 60 min
2202 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.041P)^2 + 0.2546P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2202 reflections	Δρmax = 0.24 e Å^−3
150 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.010 (2)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F13	1.17541 (17)	0.44310 (8)	0.57107 (7)	0.0682 (3)
O1	1.08628 (14)	0.05792 (8)	0.40298 (6)	0.0424 (2)
C1	0.89463 (19)	0.09679 (10)	0.41387 (7)	0.0313 (2)
N1	0.69589 (18)	0.05971 (9)	0.36815 (7)	0.0369 (2)
H1	0.581 (3)	0.1067 (14)	0.3687 (10)	0.046 (4)*
C11	0.85955 (19)	0.19237 (10)	0.47948 (7)	0.0316 (2)
C12	1.0360 (2)	0.27466 (10)	0.49496 (8)	0.0364 (3)
H12	1.1697	0.2710	0.4648	0.044*
C13	1.0067 (2)	0.36146 (11)	0.55610 (9)	0.0444 (3)
C14	0.8139 (3)	0.36913 (13)	0.60300 (9)	0.0524 (4)
H14	0.7994	0.4292	0.6439	0.063*
C15	0.6427 (2)	0.28571 (14)	0.58796 (9)	0.0502 (3)
H15	0.5121	0.2886	0.6199	0.060*
C16	0.6625 (2)	0.19779 (12)	0.52609 (8)	0.0406 (3)
H16	0.5447	0.1426	0.5157	0.049*
C21	0.67165 (19)	−0.03339 (9)	0.30790 (7)	0.0308 (2)
C22	0.4639 (2)	−0.04292 (10)	0.25615 (8)	0.0372 (3)
H22	0.3472	0.0126	0.2610	0.045*
C23	0.4337 (2)	−0.13541 (11)	0.19793 (8)	0.0412 (3)
H23	0.2945	−0.1396	0.1635	0.049*
N24	0.59093 (18)	−0.21993 (9)	0.18739 (7)	0.0405 (3)
C25	0.7890 (2)	−0.20900 (10)	0.23757 (8)	0.0380 (3)
H25	0.9018	−0.2663	0.2316	0.046*
C26	0.83920 (19)	−0.11932 (10)	0.29759 (7)	0.0348 (3)
H26	0.9812	−0.1165	0.3302	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F13	0.0714 (6)	0.0470 (5)	0.0830 (7)	−0.0086 (4)	−0.0148 (5)	−0.0205 (4)
O1	0.0360 (4)	0.0400 (5)	0.0516 (5)	0.0009 (3)	0.0067 (4)	−0.0102 (4)
C1	0.0368 (6)	0.0276 (5)	0.0296 (5)	0.0013 (4)	0.0025 (4)	0.0021 (4)
N1	0.0369 (5)	0.0340 (5)	0.0390 (5)	0.0088 (4)	−0.0034 (4)	−0.0081 (4)
C11	0.0373 (6)	0.0298 (5)	0.0271 (5)	0.0056 (4)	−0.0019 (4)	0.0018 (4)
C12	0.0398 (6)	0.0345 (6)	0.0341 (6)	0.0036 (5)	−0.0019 (5)	0.0005 (5)
C13	0.0532 (7)	0.0339 (6)	0.0437 (7)	0.0029 (5)	−0.0130 (6)	−0.0053 (5)
C14	0.0672 (9)	0.0486 (8)	0.0404 (7)	0.0193 (7)	−0.0037 (6)	−0.0143 (6)
C15	0.0510 (7)	0.0598 (9)	0.0406 (7)	0.0156 (6)	0.0078 (6)	−0.0060 (6)
C16	0.0404 (6)	0.0442 (7)	0.0374 (6)	0.0041 (5)	0.0036 (5)	−0.0002 (5)
C21	0.0361 (5)	0.0285 (5)	0.0280 (5)	−0.0003 (4)	0.0035 (4)	0.0012 (4)
C22	0.0345 (6)	0.0348 (6)	0.0418 (6)	0.0044 (5)	0.0000 (5)	−0.0021 (5)
C23	0.0376 (6)	0.0418 (7)	0.0428 (6)	−0.0010 (5)	−0.0055 (5)	−0.0045 (5)
N24	0.0437 (6)	0.0383 (5)	0.0390 (5)	−0.0008 (4)	0.0003 (4)	−0.0079 (4)
C25	0.0402 (6)	0.0347 (6)	0.0392 (6)	0.0052 (5)	0.0031 (5)	−0.0044 (5)
C26	0.0347 (6)	0.0349 (6)	0.0343 (6)	0.0033 (5)	−0.0011 (4)	−0.0020 (5)

Geometric parameters (Å, º)

F13—C13	1.3517 (16)	C15—C16	1.3805 (18)
O1—C1	1.2173 (13)	C15—H15	0.9300
C1—N1	1.3672 (15)	C16—H16	0.9300
C1—C11	1.4962 (15)	C21—C26	1.3908 (15)
N1—C21	1.3968 (14)	C21—C22	1.3938 (16)
N1—H1	0.852 (15)	C22—C23	1.3742 (17)
C11—C12	1.3898 (16)	C22—H22	0.9300
C11—C16	1.3904 (16)	C23—N24	1.3383 (16)
C12—C13	1.3724 (17)	C23—H23	0.9300
C12—H12	0.9300	N24—C25	1.3371 (16)
C13—C14	1.373 (2)	C25—C26	1.3819 (16)
C14—C15	1.376 (2)	C25—H25	0.9300
C14—H14	0.9300	C26—H26	0.9300
O1—C1—N1	124.25 (10)	C16—C15—H15	119.6
O1—C1—C11	121.48 (10)	C15—C16—C11	119.56 (12)
N1—C1—C11	114.27 (9)	C15—C16—H16	120.2
C1—N1—C21	127.30 (10)	C11—C16—H16	120.2
C1—N1—H1	115.6 (10)	C26—C21—C22	117.60 (10)
C21—N1—H1	115.9 (10)	C26—C21—N1	124.29 (10)
C12—C11—C16	120.39 (11)	C22—C21—N1	118.09 (10)
C12—C11—C1	117.53 (10)	C23—C22—C21	119.20 (11)
C16—C11—C1	122.04 (11)	C23—C22—H22	120.4
C13—C12—C11	117.86 (11)	C21—C22—H22	120.4
C13—C12—H12	121.1	N24—C23—C22	124.41 (11)
C11—C12—H12	121.1	N24—C23—H23	117.8
F13—C13—C12	118.58 (13)	C22—C23—H23	117.8
F13—C13—C14	118.39 (12)	C25—N24—C23	115.40 (10)
C12—C13—C14	123.02 (13)	N24—C25—C26	125.19 (11)
C13—C14—C15	118.34 (12)	N24—C25—H25	117.4
C13—C14—H14	120.8	C26—C25—H25	117.4
C15—C14—H14	120.8	C25—C26—C21	118.20 (10)
C14—C15—C16	120.80 (13)	C25—C26—H26	120.9
C14—C15—H15	119.6	C21—C26—H26	120.9
O1—C1—N1—C21	5.86 (19)	C14—C15—C16—C11	1.1 (2)
C11—C1—N1—C21	−174.83 (10)	C12—C11—C16—C15	0.08 (18)
O1—C1—C11—C12	31.61 (15)	C1—C11—C16—C15	177.86 (11)
N1—C1—C11—C12	−147.72 (10)	C1—N1—C21—C26	13.64 (18)
O1—C1—C11—C16	−146.23 (12)	C1—N1—C21—C22	−168.08 (11)
N1—C1—C11—C16	34.44 (15)	C26—C21—C22—C23	−0.01 (17)
C16—C11—C12—C13	−1.08 (17)	N1—C21—C22—C23	−178.41 (11)
C1—C11—C12—C13	−178.96 (10)	C21—C22—C23—N24	0.8 (2)
C11—C12—C13—F13	−179.14 (10)	C22—C23—N24—C25	−0.83 (19)
C11—C12—C13—C14	1.00 (19)	C23—N24—C25—C26	0.17 (18)
F13—C13—C14—C15	−179.75 (12)	N24—C25—C26—C21	0.53 (19)
C12—C13—C14—C15	0.1 (2)	C22—C21—C26—C25	−0.58 (16)
C13—C14—C15—C16	−1.2 (2)	N1—C21—C26—C25	177.71 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N24^i	0.852 (15)	2.333 (16)	3.0786 (14)	146.5 (13)
C26—H26···O1	0.93	2.32	2.8819 (14)	118

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

(Fop-10-125) 2-Fluoro-N-(pyridin-4-yl)benzamide

Crystal data

C12H9FN2O	F(000) = 448
Mr = 216.21	Dx = 1.422 Mg m^−3
Monoclinic, P21/c	Melting point: 408 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.0388 (1) Å	Cell parameters from 4543 reflections
b = 11.2502 (2) Å	θ = 2.6–27.5°
c = 14.9265 (3) Å	µ = 0.11 mm^−1
β = 95.310 (2)°	T = 294 K
V = 1009.72 (3) Å^3	Block, colourless
Z = 4	0.45 × 0.30 × 0.08 mm

Data collection

Xcalibur, Sapphire3, Gemini Ultra diffractometer	1914 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.016
Graphite monochromator	θmax = 27.9°, θmin = 2.3°
ω scans	h = −7→7
Absorption correction: analytical (ABSFAC, Clark and Reid, 1998)	k = −14→14
Tmin = 0.954, Tmax = 0.992	l = −19→19
7133 measured reflections	7343 standard reflections every 60 min
2256 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0515P)^2 + 0.2002P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
2256 reflections	Δρmax = 0.23 e Å^−3
150 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.037 (4)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F12	0.53290 (13)	0.13954 (8)	0.52577 (6)	0.0569 (3)
O1	1.07477 (15)	0.05676 (9)	0.40003 (7)	0.0509 (3)
C1	0.8959 (2)	0.09855 (10)	0.41433 (8)	0.0339 (3)
N1	0.69998 (19)	0.06499 (10)	0.37006 (7)	0.0413 (3)
H1	0.585 (3)	0.1091 (16)	0.3746 (11)	0.060 (5)*
C11	0.8825 (2)	0.19698 (10)	0.48148 (7)	0.0341 (3)
C12	0.7071 (2)	0.21405 (11)	0.53372 (8)	0.0406 (3)
C13	0.7051 (3)	0.30451 (14)	0.59594 (10)	0.0548 (4)
H13	0.5857	0.3134	0.6305	0.066*
C14	0.8825 (3)	0.38120 (14)	0.60592 (10)	0.0603 (4)
H14	0.8823	0.4434	0.6470	0.072*
C15	1.0608 (3)	0.36688 (12)	0.55561 (10)	0.0526 (4)
H15	1.1802	0.4193	0.5627	0.063*
C16	1.0617 (2)	0.27447 (11)	0.49463 (8)	0.0416 (3)
H16	1.1840	0.2640	0.4619	0.050*
C21	0.6637 (2)	−0.02698 (10)	0.30768 (7)	0.0346 (3)
C22	0.4564 (2)	−0.03401 (12)	0.25901 (9)	0.0445 (3)
H22	0.3466	0.0217	0.2678	0.053*
C23	0.4160 (2)	−0.12456 (13)	0.19762 (10)	0.0495 (3)
H23	0.2770	−0.1272	0.1652	0.059*
N24	0.5627 (2)	−0.20888 (10)	0.18154 (8)	0.0473 (3)
C25	0.7594 (2)	−0.20090 (11)	0.22963 (9)	0.0427 (3)
H25	0.8648	−0.2587	0.2202	0.051*
C26	0.8192 (2)	−0.11361 (11)	0.29233 (8)	0.0383 (3)
H26	0.9599	−0.1129	0.3234	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F12	0.0477 (5)	0.0689 (6)	0.0560 (5)	−0.0074 (4)	0.0157 (4)	−0.0076 (4)
O1	0.0404 (5)	0.0507 (6)	0.0628 (6)	0.0019 (4)	0.0107 (4)	−0.0180 (5)
C1	0.0404 (6)	0.0301 (5)	0.0316 (6)	0.0025 (5)	0.0058 (5)	0.0019 (4)
N1	0.0401 (6)	0.0397 (6)	0.0432 (6)	0.0094 (5)	−0.0011 (5)	−0.0109 (5)
C11	0.0415 (6)	0.0316 (6)	0.0287 (5)	0.0057 (5)	0.0003 (5)	0.0017 (4)
C12	0.0425 (7)	0.0432 (7)	0.0359 (6)	0.0059 (5)	0.0031 (5)	−0.0003 (5)
C13	0.0614 (9)	0.0587 (9)	0.0455 (8)	0.0151 (7)	0.0105 (7)	−0.0097 (7)
C14	0.0823 (11)	0.0469 (8)	0.0506 (8)	0.0102 (8)	0.0012 (8)	−0.0185 (7)
C15	0.0644 (9)	0.0398 (7)	0.0518 (8)	−0.0038 (6)	−0.0042 (7)	−0.0062 (6)
C16	0.0472 (7)	0.0397 (7)	0.0376 (6)	0.0004 (5)	0.0017 (5)	0.0009 (5)
C21	0.0422 (6)	0.0319 (6)	0.0301 (5)	0.0002 (5)	0.0060 (5)	−0.0007 (4)
C22	0.0398 (7)	0.0445 (7)	0.0490 (7)	0.0040 (5)	0.0035 (5)	−0.0081 (6)
C23	0.0431 (7)	0.0520 (8)	0.0526 (8)	−0.0040 (6)	−0.0007 (6)	−0.0112 (6)
N24	0.0525 (7)	0.0425 (6)	0.0469 (6)	−0.0042 (5)	0.0052 (5)	−0.0111 (5)
C25	0.0507 (7)	0.0358 (6)	0.0422 (7)	0.0046 (5)	0.0081 (6)	−0.0049 (5)
C26	0.0430 (7)	0.0363 (6)	0.0353 (6)	0.0044 (5)	0.0022 (5)	−0.0009 (5)

Geometric parameters (Å, º)

F12—C12	1.3420 (15)	C15—C16	1.3822 (18)
O1—C1	1.2149 (15)	C15—H15	0.9300
C1—N1	1.3544 (16)	C16—H16	0.9300
C1—C11	1.5008 (16)	C21—C26	1.3872 (17)
N1—C21	1.3957 (15)	C21—C22	1.3898 (17)
N1—H1	0.862 (18)	C22—C23	1.3768 (19)
C11—C12	1.3855 (18)	C22—H22	0.9300
C11—C16	1.3890 (18)	C23—N24	1.3348 (18)
C12—C13	1.3786 (19)	C23—H23	0.9300
C13—C14	1.373 (2)	N24—C25	1.3327 (17)
C13—H13	0.9300	C25—C26	1.3813 (17)
C14—C15	1.378 (2)	C25—H25	0.9300
C14—H14	0.9300	C26—H26	0.9300
O1—C1—N1	123.86 (11)	C16—C15—H15	120.1
O1—C1—C11	120.43 (11)	C15—C16—C11	120.97 (13)
N1—C1—C11	115.65 (10)	C15—C16—H16	119.5
C1—N1—C21	127.48 (11)	C11—C16—H16	119.5
C1—N1—H1	118.5 (11)	C26—C21—C22	117.67 (11)
C21—N1—H1	113.6 (11)	C26—C21—N1	124.33 (11)
C12—C11—C16	117.35 (11)	C22—C21—N1	117.98 (11)
C12—C11—C1	124.70 (11)	C23—C22—C21	119.04 (12)
C16—C11—C1	117.91 (11)	C23—C22—H22	120.5
F12—C12—C13	117.69 (12)	C21—C22—H22	120.5
F12—C12—C11	119.85 (11)	N24—C23—C22	124.46 (13)
C13—C12—C11	122.45 (13)	N24—C23—H23	117.8
C14—C13—C12	118.78 (14)	C22—C23—H23	117.8
C14—C13—H13	120.6	C25—N24—C23	115.37 (11)
C12—C13—H13	120.6	N24—C25—C26	125.23 (12)
C13—C14—C15	120.57 (13)	N24—C25—H25	117.4
C13—C14—H14	119.7	C26—C25—H25	117.4
C15—C14—H14	119.7	C25—C26—C21	118.22 (12)
C14—C15—C16	119.85 (14)	C25—C26—H26	120.9
C14—C15—H15	120.1	C21—C26—H26	120.9
O1—C1—N1—C21	5.8 (2)	C14—C15—C16—C11	1.6 (2)
C11—C1—N1—C21	−176.87 (11)	C12—C11—C16—C15	−1.89 (18)
O1—C1—C11—C12	−148.22 (12)	C1—C11—C16—C15	−179.81 (11)
N1—C1—C11—C12	34.32 (16)	C1—N1—C21—C26	12.0 (2)
O1—C1—C11—C16	29.53 (17)	C1—N1—C21—C22	−169.47 (12)
N1—C1—C11—C16	−147.93 (11)	C26—C21—C22—C23	−0.84 (19)
C16—C11—C12—F12	−177.94 (10)	N1—C21—C22—C23	−179.46 (12)
C1—C11—C12—F12	−0.18 (18)	C21—C22—C23—N24	0.8 (2)
C16—C11—C12—C13	0.80 (19)	C22—C23—N24—C25	−0.2 (2)
C1—C11—C12—C13	178.56 (12)	C23—N24—C25—C26	−0.4 (2)
F12—C12—C13—C14	179.38 (13)	N24—C25—C26—C21	0.4 (2)
C11—C12—C13—C14	0.6 (2)	C22—C21—C26—C25	0.28 (17)
C12—C13—C14—C15	−1.0 (2)	N1—C21—C26—C25	178.81 (12)
C13—C14—C15—C16	−0.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N24^i	0.862 (18)	2.356 (18)	3.0587 (16)	138.9 (15)
N1—H1···F12	0.862 (18)	2.332 (17)	2.7491 (13)	110.0 (13)

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

(Fpm_O-10-127) 4-Fluoro-N-(pyridin-3-yl)benzamide

Crystal data

C12H9FN2O	F(000) = 448
Mr = 216.21	Dx = 1.447 Mg m^−3
Monoclinic, P21/n	Melting point: 421 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 13.9411 (3) Å	Cell parameters from 6156 reflections
b = 5.2040 (1) Å	θ = 2.6–27.5°
c = 15.0752 (3) Å	µ = 0.11 mm^−1
β = 114.812 (3)°	T = 294 K
V = 992.74 (3) Å^3	Block, colourless
Z = 4	0.51 × 0.49 × 0.32 mm

Data collection

Xcalibur, Sapphire3, Gemini Ultra diffractometer	2338 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.012
Graphite monochromator	θmax = 29.6°, θmin = 2.6°
ω scans	h = −19→18
Absorption correction: analytical (ABSFAC, Clark and Reid, 1998)	k = −6→7
Tmin = 0.947, Tmax = 0.966	l = −20→20
8861 measured reflections	9494 standard reflections every 60 min
2624 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0519P)^2 + 0.3065P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2624 reflections	Δρmax = 0.25 e Å^−3
150 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (3)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F14	0.90021 (7)	0.1346 (2)	−0.04677 (7)	0.0661 (3)
O1	0.61595 (9)	−0.33340 (17)	0.14280 (9)	0.0553 (3)
C1	0.63029 (9)	−0.1073 (2)	0.12902 (8)	0.0334 (2)
N1	0.58246 (8)	0.08878 (19)	0.15340 (7)	0.0338 (2)
H1	0.5976 (12)	0.243 (3)	0.1431 (11)	0.044 (4)*
C11	0.70251 (8)	−0.0311 (2)	0.08326 (8)	0.0308 (2)
C12	0.78845 (9)	−0.1890 (2)	0.09844 (9)	0.0364 (3)
H12	0.8002	−0.3341	0.1376	0.044*
C13	0.85672 (10)	−0.1329 (3)	0.05593 (10)	0.0427 (3)
H13	0.9152	−0.2360	0.0671	0.051*
C14	0.83564 (10)	0.0796 (3)	−0.00319 (9)	0.0399 (3)
C15	0.75105 (10)	0.2392 (2)	−0.02129 (9)	0.0387 (3)
H15	0.7388	0.3809	−0.0622	0.046*
C16	0.68448 (9)	0.1830 (2)	0.02329 (9)	0.0362 (3)
H16	0.6272	0.2895	0.0130	0.043*
C21	0.50573 (8)	0.0640 (2)	0.19131 (8)	0.0300 (2)
C22	0.42809 (10)	0.2510 (2)	0.16657 (9)	0.0374 (3)
H22	0.4296	0.3836	0.1258	0.045*
N23	0.35152 (9)	0.2531 (2)	0.19733 (9)	0.0446 (3)
C24	0.35111 (11)	0.0602 (3)	0.25561 (10)	0.0440 (3)
H24	0.2977	0.0556	0.2772	0.053*
C25	0.42583 (11)	−0.1324 (3)	0.28530 (9)	0.0425 (3)
H25	0.4227	−0.2619	0.3265	0.051*
C26	0.50551 (10)	−0.1321 (2)	0.25341 (9)	0.0369 (3)
H26	0.5572	−0.2592	0.2730	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F14	0.0582 (5)	0.0835 (7)	0.0797 (6)	0.0152 (5)	0.0514 (5)	0.0249 (5)
O1	0.0769 (7)	0.0246 (4)	0.0917 (8)	0.0005 (4)	0.0621 (6)	0.0012 (5)
C1	0.0372 (5)	0.0267 (5)	0.0407 (6)	0.0001 (4)	0.0208 (5)	−0.0003 (4)
N1	0.0399 (5)	0.0240 (4)	0.0467 (5)	−0.0006 (4)	0.0273 (4)	0.0011 (4)
C11	0.0333 (5)	0.0279 (5)	0.0340 (5)	0.0005 (4)	0.0169 (4)	−0.0023 (4)
C12	0.0362 (6)	0.0342 (6)	0.0394 (6)	0.0063 (4)	0.0167 (5)	0.0049 (5)
C13	0.0345 (6)	0.0466 (7)	0.0500 (7)	0.0111 (5)	0.0207 (5)	0.0053 (6)
C14	0.0369 (6)	0.0483 (7)	0.0418 (6)	0.0005 (5)	0.0238 (5)	0.0013 (5)
C15	0.0458 (6)	0.0352 (6)	0.0412 (6)	0.0041 (5)	0.0241 (5)	0.0055 (5)
C16	0.0394 (6)	0.0316 (6)	0.0433 (6)	0.0075 (4)	0.0230 (5)	0.0031 (5)
C21	0.0330 (5)	0.0267 (5)	0.0341 (5)	−0.0036 (4)	0.0178 (4)	−0.0038 (4)
C22	0.0421 (6)	0.0299 (5)	0.0468 (6)	0.0020 (5)	0.0252 (5)	0.0029 (5)
N23	0.0440 (6)	0.0397 (6)	0.0604 (7)	0.0026 (5)	0.0321 (5)	−0.0020 (5)
C24	0.0466 (7)	0.0446 (7)	0.0534 (7)	−0.0092 (5)	0.0333 (6)	−0.0092 (6)
C25	0.0543 (7)	0.0378 (6)	0.0443 (6)	−0.0088 (5)	0.0295 (6)	0.0007 (5)
C26	0.0421 (6)	0.0322 (6)	0.0393 (6)	0.0001 (5)	0.0199 (5)	0.0028 (4)

Geometric parameters (Å, º)

F14—C14	1.3490 (13)	C15—C16	1.3864 (16)
O1—C1	1.2259 (14)	C15—H15	0.9300
C1—N1	1.3514 (14)	C16—H16	0.9300
C1—C11	1.4933 (15)	C21—C22	1.3848 (16)
N1—C21	1.4144 (13)	C21—C26	1.3859 (16)
N1—H1	0.859 (17)	C22—N23	1.3305 (15)
C11—C16	1.3894 (16)	C22—H22	0.9300
C11—C12	1.3904 (15)	N23—C24	1.3358 (18)
C12—C13	1.3835 (17)	C24—C25	1.378 (2)
C12—H12	0.9300	C24—H24	0.9300
C13—C14	1.3725 (19)	C25—C26	1.3833 (16)
C13—H13	0.9300	C25—H25	0.9300
C14—C15	1.3729 (17)	C26—H26	0.9300
O1—C1—N1	122.98 (11)	C16—C15—H15	121.0
O1—C1—C11	121.51 (10)	C15—C16—C11	120.63 (10)
N1—C1—C11	115.50 (10)	C15—C16—H16	119.7
C1—N1—C21	125.76 (10)	C11—C16—H16	119.7
C1—N1—H1	117.9 (10)	C22—C21—C26	118.45 (10)
C21—N1—H1	116.3 (10)	C22—C21—N1	117.73 (10)
C16—C11—C12	119.29 (10)	C26—C21—N1	123.80 (10)
C16—C11—C1	122.72 (10)	N23—C22—C21	124.25 (11)
C12—C11—C1	117.93 (10)	N23—C22—H22	117.9
C13—C12—C11	120.76 (11)	C21—C22—H22	117.9
C13—C12—H12	119.6	C22—N23—C24	116.64 (11)
C11—C12—H12	119.6	N23—C24—C25	123.31 (11)
C14—C13—C12	118.01 (11)	N23—C24—H24	118.3
C14—C13—H13	121.0	C25—C24—H24	118.3
C12—C13—H13	121.0	C24—C25—C26	119.61 (11)
F14—C14—C13	118.83 (11)	C24—C25—H25	120.2
F14—C14—C15	117.91 (12)	C26—C25—H25	120.2
C13—C14—C15	123.26 (11)	C25—C26—C21	117.73 (11)
C14—C15—C16	118.03 (11)	C25—C26—H26	121.1
C14—C15—H15	121.0	C21—C26—H26	121.1
O1—C1—N1—C21	−4.3 (2)	C14—C15—C16—C11	−0.93 (19)
C11—C1—N1—C21	175.46 (10)	C12—C11—C16—C15	0.12 (18)
O1—C1—C11—C16	146.70 (13)	C1—C11—C16—C15	−176.93 (11)
N1—C1—C11—C16	−33.10 (16)	C1—N1—C21—C22	−147.25 (12)
O1—C1—C11—C12	−30.39 (17)	C1—N1—C21—C26	34.42 (18)
N1—C1—C11—C12	149.82 (11)	C26—C21—C22—N23	−1.13 (18)
C16—C11—C12—C13	1.08 (18)	N1—C21—C22—N23	−179.55 (11)
C1—C11—C12—C13	178.27 (11)	C21—C22—N23—C24	−0.13 (19)
C11—C12—C13—C14	−1.42 (19)	C22—N23—C24—C25	1.1 (2)
C12—C13—C14—F14	−178.74 (12)	N23—C24—C25—C26	−0.7 (2)
C12—C13—C14—C15	0.6 (2)	C24—C25—C26—C21	−0.61 (18)
F14—C14—C15—C16	179.91 (11)	C22—C21—C26—C25	1.45 (17)
C13—C14—C15—C16	0.6 (2)	N1—C21—C26—C25	179.76 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.859 (17)	2.221 (17)	3.0575 (13)	164.6 (14)
C26—H26···O1	0.93	2.45	2.8987 (15)	109

Symmetry code: (i) x, y+1, z.

(Fpm_N-10-121) 4-Fluoro-N-(pyridin-3-yl)benzamide

Crystal data

C12H9FN2O	F(000) = 448
Mr = 216.21	Dx = 1.422 Mg m^−3
Monoclinic, P21/n	Melting point: 423 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 3.9077 (2) Å	Cell parameters from 1505 reflections
b = 24.2444 (12) Å	θ = 2.6–27.5°
c = 10.7012 (5) Å	µ = 0.11 mm^−1
β = 95.181 (5)°	T = 294 K
V = 1009.69 (9) Å^3	Block, colourless
Z = 4	0.24 × 0.05 × 0.03 mm

Data collection

Xcalibur, Sapphire3, Gemini Ultra diffractometer	1154 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.049
Graphite monochromator	θmax = 27.4°, θmin = 2.1°
ω scans	h = −5→4
Absorption correction: analytical (ABSFAC, Clark and Reid, 1998)	k = −31→31
Tmin = 0.975, Tmax = 0.997	l = −13→13
6537 measured reflections	6646 standard reflections every 60 min
2162 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ^2(Fo^2) + (0.027P)^2] where P = (Fo^2 + 2Fc^2)/3
2162 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F14	0.2906 (5)	−0.04664 (7)	0.14409 (16)	0.0977 (6)
O1	0.9086 (5)	0.13840 (8)	0.50443 (16)	0.0803 (6)
C1	0.8398 (6)	0.14048 (10)	0.3905 (2)	0.0510 (6)
N1	0.9083 (5)	0.18577 (8)	0.3220 (2)	0.0489 (5)
H1	0.856 (6)	0.1854 (10)	0.244 (3)	0.065 (8)*
C11	0.6861 (6)	0.09229 (9)	0.3203 (2)	0.0459 (6)
C12	0.7182 (7)	0.04148 (10)	0.3780 (2)	0.0608 (7)
H12	0.8284	0.0391	0.4586	0.073*
C13	0.5919 (7)	−0.00553 (11)	0.3198 (3)	0.0703 (8)
H13	0.6202	−0.0397	0.3588	0.084*
C14	0.4227 (7)	−0.00075 (11)	0.2025 (3)	0.0637 (7)
C15	0.3809 (6)	0.04843 (11)	0.1424 (2)	0.0584 (7)
H15	0.2653	0.0505	0.0626	0.070*
C16	0.5127 (6)	0.09519 (10)	0.2015 (2)	0.0500 (6)
H16	0.4852	0.1291	0.1614	0.060*
C21	1.0631 (5)	0.23532 (9)	0.3654 (2)	0.0437 (6)
C22	1.1297 (6)	0.24915 (10)	0.4914 (2)	0.0531 (6)
H22	1.0721	0.2239	0.5516	0.064*
N23	1.2724 (6)	0.29689 (8)	0.52998 (18)	0.0595 (6)
C24	1.3530 (7)	0.33274 (10)	0.4437 (2)	0.0602 (7)
H24	1.4490	0.3663	0.4702	0.072*
C25	1.3012 (6)	0.32256 (10)	0.3172 (2)	0.0555 (7)
H25	1.3645	0.3484	0.2593	0.067*
C26	1.1541 (6)	0.27355 (10)	0.2784 (2)	0.0510 (6)
H26	1.1151	0.2659	0.1931	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F14	0.1541 (16)	0.0589 (10)	0.0775 (13)	−0.0296 (11)	−0.0042 (11)	−0.0125 (9)
O1	0.1340 (17)	0.0709 (13)	0.0328 (11)	−0.0207 (12)	−0.0111 (10)	0.0053 (9)
C1	0.0675 (16)	0.0503 (15)	0.0344 (14)	0.0018 (13)	0.0004 (12)	0.0020 (11)
N1	0.0713 (14)	0.0467 (12)	0.0275 (11)	−0.0011 (11)	−0.0029 (10)	−0.0017 (9)
C11	0.0587 (14)	0.0442 (13)	0.0345 (13)	−0.0005 (12)	0.0027 (11)	0.0031 (11)
C12	0.0855 (19)	0.0517 (16)	0.0432 (15)	−0.0023 (14)	−0.0055 (13)	0.0081 (12)
C13	0.103 (2)	0.0483 (17)	0.0588 (19)	−0.0003 (15)	0.0020 (16)	0.0083 (14)
C14	0.092 (2)	0.0485 (16)	0.0510 (17)	−0.0129 (14)	0.0058 (15)	−0.0081 (13)
C15	0.0762 (17)	0.0557 (16)	0.0420 (15)	−0.0072 (14)	−0.0028 (12)	−0.0030 (12)
C16	0.0642 (15)	0.0451 (14)	0.0399 (14)	0.0009 (12)	0.0005 (11)	0.0054 (11)
C21	0.0548 (14)	0.0445 (13)	0.0308 (12)	0.0053 (11)	−0.0012 (10)	−0.0023 (10)
C22	0.0798 (18)	0.0513 (15)	0.0272 (12)	0.0012 (13)	−0.0004 (11)	−0.0003 (11)
N23	0.0942 (16)	0.0471 (12)	0.0346 (12)	0.0008 (12)	−0.0077 (11)	−0.0055 (10)
C24	0.0870 (19)	0.0464 (14)	0.0438 (16)	−0.0001 (14)	−0.0123 (13)	−0.0041 (12)
C25	0.0794 (17)	0.0476 (15)	0.0380 (14)	−0.0046 (13)	−0.0035 (12)	0.0014 (11)
C26	0.0712 (16)	0.0511 (15)	0.0293 (13)	0.0018 (13)	−0.0029 (11)	−0.0002 (11)

Geometric parameters (Å, º)

F14—C14	1.355 (3)	C15—C16	1.375 (3)
O1—C1	1.225 (3)	C15—H15	0.9300
C1—N1	1.360 (3)	C16—H16	0.9300
C1—C11	1.486 (3)	C21—C26	1.383 (3)
N1—C21	1.405 (3)	C21—C22	1.391 (3)
N1—H1	0.84 (3)	C22—N23	1.334 (3)
C11—C12	1.379 (3)	C22—H22	0.9300
C11—C16	1.387 (3)	N23—C24	1.326 (3)
C12—C13	1.369 (3)	C24—C25	1.373 (3)
C12—H12	0.9300	C24—H24	0.9300
C13—C14	1.369 (4)	C25—C26	1.368 (3)
C13—H13	0.9300	C25—H25	0.9300
C14—C15	1.358 (3)	C26—H26	0.9300
O1—C1—N1	122.2 (2)	C16—C15—H15	120.6
O1—C1—C11	120.9 (2)	C15—C16—C11	120.8 (2)
N1—C1—C11	116.9 (2)	C15—C16—H16	119.6
C1—N1—C21	127.7 (2)	C11—C16—H16	119.6
C1—N1—H1	118.9 (18)	C26—C21—C22	117.0 (2)
C21—N1—H1	113.4 (18)	C26—C21—N1	118.6 (2)
C12—C11—C16	118.2 (2)	C22—C21—N1	124.3 (2)
C12—C11—C1	117.4 (2)	N23—C22—C21	123.0 (2)
C16—C11—C1	124.4 (2)	N23—C22—H22	118.5
C13—C12—C11	121.7 (2)	C21—C22—H22	118.5
C13—C12—H12	119.2	C24—N23—C22	118.2 (2)
C11—C12—H12	119.2	N23—C24—C25	123.0 (2)
C12—C13—C14	118.1 (2)	N23—C24—H24	118.5
C12—C13—H13	121.0	C25—C24—H24	118.5
C14—C13—H13	121.0	C26—C25—C24	118.4 (2)
F14—C14—C15	118.5 (2)	C26—C25—H25	120.8
F14—C14—C13	119.1 (2)	C24—C25—H25	120.8
C15—C14—C13	122.4 (2)	C25—C26—C21	120.3 (2)
C14—C15—C16	118.8 (2)	C25—C26—H26	119.9
C14—C15—H15	120.6	C21—C26—H26	119.9
O1—C1—N1—C21	0.6 (4)	C14—C15—C16—C11	0.2 (4)
C11—C1—N1—C21	−177.6 (2)	C12—C11—C16—C15	−0.9 (3)
O1—C1—C11—C12	−18.9 (3)	C1—C11—C16—C15	179.3 (2)
N1—C1—C11—C12	159.2 (2)	C1—N1—C21—C26	171.0 (2)
O1—C1—C11—C16	160.8 (2)	C1—N1—C21—C22	−9.6 (4)
N1—C1—C11—C16	−21.0 (3)	C26—C21—C22—N23	0.4 (3)
C16—C11—C12—C13	1.7 (4)	N1—C21—C22—N23	−179.0 (2)
C1—C11—C12—C13	−178.5 (2)	C21—C22—N23—C24	0.2 (4)
C11—C12—C13—C14	−1.7 (4)	C22—N23—C24—C25	−1.0 (4)
C12—C13—C14—F14	−178.9 (2)	N23—C24—C25—C26	1.2 (4)
C12—C13—C14—C15	0.9 (4)	C24—C25—C26—C21	−0.5 (4)
F14—C14—C15—C16	179.6 (2)	C22—C21—C26—C25	−0.3 (3)
C13—C14—C15—C16	−0.2 (4)	N1—C21—C26—C25	179.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N23^i	0.84 (3)	2.32 (3)	3.151 (3)	167 (2)
C22—H22···O1	0.93	2.21	2.828 (3)	123
C16—H16···N23^i	0.93	2.60	3.404 (3)	146
C26—H26···N23^i	0.93	2.60	3.390 (3)	144

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

(Fmm-10-122) 3-Fluoro-N-(pyridin-3-yl)benzamide

Crystal data

C12H9FN2O	Dx = 1.408 Mg m^−3
Mr = 216.21	Melting point: 424 K
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3744 reflections
a = 11.3020 (3) Å	θ = 2.6–27.5°
b = 11.8371 (3) Å	µ = 0.11 mm^−1
c = 7.6218 (2) Å	T = 294 K
V = 1019.67 (5) Å^3	Block, colourless
Z = 4	0.38 × 0.10 × 0.08 mm
F(000) = 448

Data collection

Xcalibur, Sapphire3, Gemini Ultra diffractometer	981 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.021
Graphite monochromator	θmax = 27.8°, θmin = 2.5°
ω scans	h = −14→14
Absorption correction: analytical (ABSFAC, Clark and Reid, 1998)	k = −14→14
Tmin = 0.961, Tmax = 0.992	l = −9→9
7366 measured reflections	7839 standard reflections every 60 min
1239 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0521P)^2] where P = (Fo^2 + 2Fc^2)/3
1239 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = 0.15 e Å^−3
1 restraint	Δρmin = −0.15 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F13	0.30425 (15)	−0.12223 (10)	0.3223 (3)	0.0941 (6)
O1	0.11724 (13)	0.26118 (12)	0.3503 (3)	0.0625 (5)
C1	0.22288 (17)	0.27534 (15)	0.3293 (3)	0.0426 (5)
N1	0.27110 (16)	0.37272 (14)	0.2715 (3)	0.0436 (4)
H1	0.338 (3)	0.380 (2)	0.254 (4)	0.066 (8)*
C11	0.30815 (16)	0.18037 (16)	0.3624 (3)	0.0427 (5)
C12	0.2688 (2)	0.07197 (14)	0.3258 (3)	0.0497 (5)
H12	0.1940	0.0599	0.2788	0.060*
C13	0.3428 (2)	−0.01694 (18)	0.3605 (4)	0.0583 (6)
C14	0.4525 (2)	−0.0041 (2)	0.4304 (4)	0.0669 (7)
H14	0.5003	−0.0664	0.4532	0.080*
C15	0.4906 (2)	0.1030 (2)	0.4663 (4)	0.0672 (7)
H15	0.5656	0.1139	0.5136	0.081*
C16	0.4191 (2)	0.19556 (18)	0.4331 (3)	0.0521 (6)
H16	0.4460	0.2680	0.4586	0.063*
C21	0.21051 (16)	0.47223 (16)	0.2236 (3)	0.0389 (4)
C22	0.09061 (18)	0.49007 (18)	0.2513 (3)	0.0485 (6)
H22	0.0464	0.4333	0.3045	0.058*
N23	0.03598 (16)	0.58587 (15)	0.2043 (3)	0.0568 (5)
C24	0.09922 (19)	0.66611 (18)	0.1271 (4)	0.0549 (6)
H24	0.0613	0.7323	0.0931	0.066*
C25	0.21805 (18)	0.65550 (18)	0.0953 (3)	0.0509 (6)
H25	0.2599	0.7136	0.0415	0.061*
C26	0.27408 (18)	0.55768 (15)	0.1443 (3)	0.0460 (5)
H26	0.3547	0.5489	0.1240	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F13	0.1067 (13)	0.0402 (7)	0.1355 (17)	−0.0016 (7)	0.0159 (13)	−0.0029 (10)
O1	0.0375 (8)	0.0469 (8)	0.1031 (15)	−0.0019 (6)	0.0128 (8)	0.0056 (10)
C1	0.0389 (11)	0.0397 (10)	0.0492 (12)	0.0001 (8)	0.0030 (10)	−0.0049 (10)
N1	0.0300 (9)	0.0397 (8)	0.0612 (11)	0.0025 (7)	0.0042 (9)	0.0016 (7)
C11	0.0413 (10)	0.0406 (10)	0.0462 (12)	0.0004 (8)	0.0040 (9)	0.0015 (9)
C12	0.0490 (12)	0.0426 (11)	0.0574 (13)	−0.0015 (9)	0.0031 (11)	−0.0010 (11)
C13	0.0638 (15)	0.0373 (11)	0.0738 (18)	0.0002 (10)	0.0162 (13)	0.0041 (12)
C14	0.0595 (15)	0.0529 (13)	0.0883 (19)	0.0138 (12)	0.0138 (14)	0.0233 (13)
C15	0.0491 (13)	0.0698 (17)	0.0826 (18)	0.0040 (12)	−0.0063 (13)	0.0229 (13)
C16	0.0478 (12)	0.0451 (12)	0.0635 (14)	−0.0027 (10)	−0.0030 (11)	0.0063 (11)
C21	0.0351 (10)	0.0361 (10)	0.0456 (11)	−0.0002 (8)	0.0001 (9)	−0.0049 (8)
C22	0.0362 (10)	0.0417 (11)	0.0677 (15)	0.0011 (8)	0.0020 (10)	0.0012 (10)
N23	0.0400 (10)	0.0450 (9)	0.0853 (15)	0.0056 (8)	−0.0006 (10)	0.0031 (10)
C24	0.0517 (14)	0.0385 (11)	0.0745 (17)	0.0040 (9)	−0.0047 (12)	0.0028 (11)
C25	0.0496 (14)	0.0414 (10)	0.0616 (14)	−0.0048 (9)	0.0053 (11)	0.0048 (10)
C26	0.0358 (11)	0.0467 (11)	0.0555 (12)	0.0005 (8)	0.0035 (10)	−0.0023 (10)

Geometric parameters (Å, º)

F13—C13	1.352 (3)	C15—C16	1.385 (3)
O1—C1	1.216 (2)	C15—H15	0.9300
C1—N1	1.349 (2)	C16—H16	0.9300
C1—C11	1.502 (3)	C21—C26	1.380 (3)
N1—C21	1.411 (2)	C21—C22	1.388 (2)
N1—H1	0.77 (3)	C22—N23	1.340 (3)
C11—C16	1.376 (3)	C22—H22	0.9300
C11—C12	1.386 (3)	N23—C24	1.326 (3)
C12—C13	1.369 (3)	C24—C25	1.370 (3)
C12—H12	0.9300	C24—H24	0.9300
C13—C14	1.359 (4)	C25—C26	1.372 (3)
C14—C15	1.367 (4)	C25—H25	0.9300
C14—H14	0.9300	C26—H26	0.9300
O1—C1—N1	123.87 (18)	C16—C15—H15	119.6
O1—C1—C11	120.31 (17)	C11—C16—C15	120.0 (2)
N1—C1—C11	115.79 (17)	C11—C16—H16	120.0
C1—N1—C21	127.01 (17)	C15—C16—H16	120.0
C1—N1—H1	123.1 (19)	C26—C21—C22	117.60 (18)
C21—N1—H1	109.8 (19)	C26—C21—N1	118.21 (16)
C16—C11—C12	119.44 (19)	C22—C21—N1	124.19 (18)
C16—C11—C1	123.53 (18)	N23—C22—C21	122.56 (19)
C12—C11—C1	116.96 (17)	N23—C22—H22	118.7
C13—C12—C11	118.5 (2)	C21—C22—H22	118.7
C13—C12—H12	120.8	C24—N23—C22	118.44 (18)
C11—C12—H12	120.8	N23—C24—C25	122.7 (2)
F13—C13—C14	118.8 (2)	N23—C24—H24	118.6
F13—C13—C12	118.1 (2)	C25—C24—H24	118.6
C14—C13—C12	123.2 (2)	C24—C25—C26	118.80 (19)
C13—C14—C15	118.0 (2)	C24—C25—H25	120.6
C13—C14—H14	121.0	C26—C25—H25	120.6
C15—C14—H14	121.0	C25—C26—C21	119.85 (19)
C14—C15—C16	120.9 (2)	C25—C26—H26	120.1
C14—C15—H15	119.6	C21—C26—H26	120.1
O1—C1—N1—C21	−1.0 (4)	C12—C11—C16—C15	0.3 (4)
C11—C1—N1—C21	177.0 (2)	C1—C11—C16—C15	177.3 (2)
O1—C1—C11—C16	−143.9 (2)	C14—C15—C16—C11	−0.3 (4)
N1—C1—C11—C16	37.9 (3)	C1—N1—C21—C26	−171.0 (2)
O1—C1—C11—C12	33.1 (3)	C1—N1—C21—C22	9.1 (3)
N1—C1—C11—C12	−145.0 (2)	C26—C21—C22—N23	−0.1 (3)
C16—C11—C12—C13	−0.5 (3)	N1—C21—C22—N23	179.9 (2)
C1—C11—C12—C13	−177.6 (2)	C21—C22—N23—C24	0.6 (4)
C11—C12—C13—F13	−179.2 (2)	C22—N23—C24—C25	−0.7 (4)
C11—C12—C13—C14	0.5 (4)	N23—C24—C25—C26	0.4 (4)
F13—C13—C14—C15	179.2 (3)	C24—C25—C26—C21	0.1 (4)
C12—C13—C14—C15	−0.5 (4)	C22—C21—C26—C25	−0.3 (3)
C13—C14—C15—C16	0.3 (4)	N1—C21—C26—C25	179.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N23^i	0.77 (3)	2.31 (3)	3.077 (3)	176 (3)
C22—H22···O1	0.93	2.22	2.829 (3)	123

Symmetry code: (i) x+1/2, −y+1, z.

(Fom_O-11-009) 2-Fluoro-N-(pyridin-3-yl)benzamide

Crystal data

C12H9FN2O	F(000) = 1344
Mr = 216.21	Dx = 1.436 Mg m^−3
Monoclinic, P21	Melting point: 363 K
Hall symbol: P 2yb	Cu Kα radiation, λ = 1.54184 Å
a = 16.2051 (4) Å	Cell parameters from 6501 reflections
b = 5.2239 (1) Å	θ = 2.6–27.5°
c = 35.8162 (9) Å	µ = 0.89 mm^−1
β = 98.405 (3)°	T = 294 K
V = 2999.41 (12) Å^3	Needle, colourless
Z = 12	0.47 × 0.23 × 0.16 mm

Data collection

Xcalibur, Sapphire3, Gemini Ultra diffractometer	5064 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 58.3°, θmin = 2.8°
ω scans	h = −17→17
Absorption correction: analytical (ABSFAC, Clark and Reid, 1998)	k = −5→5
Tmin = 0.679, Tmax = 0.870	l = −38→39
13035 measured reflections	13041 standard reflections every 60 min
5835 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.059	w = 1/[σ^2(Fo^2) + (0.099P)^2 + 1.37P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.176	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.16 e Å^−3
5835 reflections	Δρmin = −0.19 e Å^−3
1315 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
638 restraints	Extinction coefficient: 0.00067 (16)
Primary atom site location: structure-invariant direct methods	Absolute structure: (Flack, 1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.0 (13)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
F12A	0.61665 (18)	0.3940 (9)	0.20484 (7)	0.0654 (10)	0.87
O1A	0.7374 (5)	−0.2255 (11)	0.16994 (17)	0.0611 (16)	0.87
C1A	0.7222 (4)	−0.0019 (13)	0.17923 (17)	0.0513 (15)	0.87
N1A	0.7126 (3)	0.1906 (10)	0.15429 (10)	0.0486 (12)	0.87
H1A	0.7082	0.3407	0.1636	0.058*	0.87
C11A	0.7143 (3)	0.0694 (13)	0.22009 (12)	0.0440 (13)	0.87
C12A	0.6643 (3)	0.2531 (11)	0.23194 (12)	0.0457 (13)	0.87
C13A	0.6566 (3)	0.3054 (15)	0.26833 (15)	0.0577 (15)	0.87
H13A	0.6217	0.4342	0.2748	0.069*	0.87
C14A	0.7057 (5)	0.1494 (16)	0.29625 (15)	0.072 (2)	0.87
H14A	0.7051	0.1807	0.3218	0.086*	0.87
C15A	0.7523 (5)	−0.0408 (19)	0.28560 (19)	0.072 (2)	0.87
H15A	0.7828	−0.1409	0.3042	0.086*	0.87
C16A	0.7574 (4)	−0.0961 (14)	0.24792 (17)	0.0545 (15)	0.87
H16A	0.7878	−0.2356	0.2412	0.065*	0.87
C21A	0.7089 (3)	0.1803 (11)	0.11538 (12)	0.0359 (11)	0.87
C22A	0.6681 (3)	0.3736 (14)	0.09502 (16)	0.0570 (16)	0.87
H22A	0.6447	0.5016	0.1081	0.068*	0.87
N23A	0.6592 (3)	0.3929 (11)	0.05655 (11)	0.0564 (12)	0.87
C24A	0.6953 (5)	0.2069 (16)	0.03895 (17)	0.0650 (19)	0.87
H24A	0.6914	0.2148	0.0128	0.078*	0.87
C25A	0.7388 (5)	0.0004 (15)	0.05770 (18)	0.058 (2)	0.87
H25A	0.7623	−0.1256	0.0442	0.070*	0.87
C26A	0.7458 (3)	−0.0117 (12)	0.09557 (15)	0.0465 (13)	0.87
H26A	0.7748	−0.1459	0.1086	0.056*	0.87
F12B	0.11662 (19)	0.3096 (9)	0.13382 (7)	0.0630 (10)	0.83
O1B	0.2384 (7)	0.9343 (15)	0.1828 (3)	0.060 (2)	0.83
C1B	0.2210 (5)	0.7171 (12)	0.17087 (17)	0.0401 (14)	0.83
N1B	0.2154 (3)	0.5166 (9)	0.19422 (10)	0.0427 (11)	0.83
H1B	0.2098	0.3672	0.1841	0.051*	0.83
C11B	0.2096 (3)	0.6627 (11)	0.12957 (12)	0.0383 (11)	0.83
C12B	0.1568 (3)	0.4647 (13)	0.11208 (14)	0.0487 (14)	0.83
C13B	0.1456 (3)	0.4249 (14)	0.07383 (13)	0.0535 (15)	0.83
H13B	0.1124	0.2907	0.0633	0.064*	0.83
C14B	0.1838 (4)	0.5850 (14)	0.05137 (14)	0.0522 (15)	0.83
H14B	0.1774	0.5569	0.0255	0.063*	0.83
C15B	0.2313 (4)	0.7856 (18)	0.06667 (15)	0.0648 (19)	0.83
H15B	0.2544	0.8990	0.0511	0.078*	0.83
C16B	0.2450 (3)	0.8200 (14)	0.10576 (14)	0.0482 (14)	0.83
H16B	0.2791	0.9534	0.1159	0.058*	0.83
C21B	0.2179 (3)	0.5298 (13)	0.23371 (13)	0.0458 (14)	0.83
C22B	0.1794 (3)	0.3266 (12)	0.24978 (14)	0.0467 (14)	0.83
H22B	0.1553	0.1970	0.2340	0.056*	0.83
N23B	0.1754 (3)	0.3093 (13)	0.28691 (12)	0.0594 (14)	0.83
C24B	0.2110 (5)	0.4786 (15)	0.30811 (18)	0.0564 (17)	0.83
H24B	0.2092	0.4652	0.3339	0.068*	0.83
C25B	0.2543 (5)	0.6919 (18)	0.29504 (18)	0.062 (2)	0.83
H25B	0.2788	0.8167	0.3116	0.075*	0.83
C26B	0.2579 (4)	0.7040 (14)	0.25738 (15)	0.0471 (14)	0.83
H26B	0.2883	0.8338	0.2479	0.056*	0.83
F12C	1.0459 (2)	0.9066 (9)	0.20364 (7)	0.0662 (10)	0.83
O1C	0.9227 (4)	0.2770 (11)	0.15497 (15)	0.0536 (13)	0.83
C1C	0.9415 (4)	0.4960 (14)	0.16617 (16)	0.0493 (16)	0.83
N1C	0.9465 (3)	0.7003 (10)	0.14310 (11)	0.0468 (11)	0.83
H1C	0.9513	0.8484	0.1537	0.056*	0.83
C11C	0.9544 (4)	0.5719 (19)	0.20840 (15)	0.053 (2)	0.83
C12C	1.0002 (5)	0.760 (2)	0.2247 (2)	0.064 (3)	0.83
C13C	1.0161 (7)	0.815 (2)	0.2640 (3)	0.089 (5)	0.83
H13C	1.0476	0.9552	0.2736	0.107*	0.83
C14C	0.9821 (7)	0.649 (2)	0.2863 (2)	0.072 (3)	0.83
H14C	0.9921	0.6697	0.3123	0.087*	0.83
C15C	0.9322 (6)	0.445 (2)	0.2708 (2)	0.062 (3)	0.83
H15C	0.9076	0.3368	0.2866	0.075*	0.83
C16C	0.9192 (6)	0.405 (2)	0.2329 (2)	0.064 (3)	0.83
H16C	0.8870	0.2671	0.2231	0.077*	0.83
C21C	0.9447 (4)	0.6945 (14)	0.10344 (14)	0.0414 (16)	0.83
C22C	0.9853 (3)	0.8832 (14)	0.08752 (14)	0.0509 (15)	0.83
H22C	1.0122	1.0075	0.1035	0.061*	0.83
N23C	0.9896 (3)	0.9043 (12)	0.05095 (13)	0.0548 (13)	0.83
C24C	0.9524 (7)	0.702 (3)	0.02853 (17)	0.072 (4)	0.83
H24C	0.9554	0.7035	0.0028	0.086*	0.83
C25C	0.9145 (5)	0.513 (2)	0.0421 (2)	0.057 (3)	0.83
H25C	0.8898	0.3884	0.0257	0.068*	0.83
C26C	0.9090 (5)	0.490 (2)	0.0810 (2)	0.063 (3)	0.83
H26C	0.8838	0.3510	0.0909	0.076*	0.83
F12D	0.54501 (19)	−0.1874 (9)	0.12603 (7)	0.0703 (11)	0.87
O1D	0.4286 (6)	0.4349 (14)	0.1593 (3)	0.069 (2)	0.87
C1D	0.4419 (4)	0.2167 (12)	0.15033 (16)	0.0440 (13)	0.87
N1D	0.4494 (3)	0.0152 (10)	0.17516 (11)	0.0467 (11)	0.87
H1D	0.4533	−0.1357	0.1660	0.056*	0.87
C11D	0.4483 (3)	0.1584 (12)	0.11076 (13)	0.0440 (13)	0.87
C12D	0.4979 (3)	−0.0417 (14)	0.09936 (15)	0.0527 (15)	0.87
C13D	0.5013 (3)	−0.0914 (15)	0.06184 (15)	0.0570 (15)	0.87
H13D	0.5350	−0.2237	0.0555	0.068*	0.87
C14D	0.4590 (5)	0.0404 (17)	0.03548 (17)	0.068 (2)	0.87
H14D	0.4634	0.0054	0.0104	0.081*	0.87
C15D	0.4056 (6)	0.240 (2)	0.0445 (2)	0.077 (3)	0.87
H15D	0.3744	0.3352	0.0256	0.092*	0.87
C16D	0.4012 (5)	0.2878 (18)	0.08191 (18)	0.068 (2)	0.87
H16D	0.3646	0.4135	0.0879	0.081*	0.87
C21D	0.4510 (3)	0.0352 (14)	0.21442 (13)	0.0510 (15)	0.87
C22D	0.4937 (3)	−0.1670 (12)	0.23574 (13)	0.0503 (14)	0.87
H22D	0.5178	−0.2947	0.2228	0.060*	0.87
N23D	0.5012 (3)	−0.1837 (13)	0.27274 (12)	0.0655 (14)	0.87
C24D	0.4674 (3)	0.0048 (14)	0.29047 (14)	0.0545 (15)	0.87
H24D	0.4740	0.0011	0.3167	0.065*	0.87
C25D	0.4251 (4)	0.1965 (15)	0.27300 (14)	0.0581 (17)	0.87
H25D	0.4015	0.3187	0.2871	0.070*	0.87
C26D	0.4151 (3)	0.2197 (14)	0.23314 (13)	0.0487 (14)	0.87
H26D	0.3854	0.3542	0.2206	0.058*	0.87
F12E	0.7145 (3)	0.8784 (14)	0.45631 (12)	0.0638 (16)	0.50
O1E	0.588 (3)	0.257 (4)	0.4885 (12)	0.059 (7)	0.50
C1E	0.6071 (11)	0.475 (3)	0.4806 (3)	0.049 (3)	0.50
N1E	0.6165 (5)	0.6706 (19)	0.50600 (17)	0.050 (2)	0.50
H1E	0.6212	0.8214	0.4969	0.060*	0.50
C11E	0.6168 (12)	0.568 (3)	0.4407 (4)	0.045 (4)	0.50
C12E	0.6647 (9)	0.741 (3)	0.4305 (3)	0.044 (3)	0.50
C13E	0.6729 (16)	0.810 (5)	0.3930 (6)	0.072 (5)	0.50
H13E	0.7082	0.9430	0.3883	0.086*	0.50
C14E	0.6274 (18)	0.677 (7)	0.3635 (7)	0.061 (6)	0.50
H14E	0.6274	0.7268	0.3385	0.073*	0.50
C15E	0.584 (2)	0.475 (9)	0.3720 (11)	0.059 (6)	0.50
H15E	0.5548	0.3738	0.3531	0.071*	0.50
C16E	0.5823 (11)	0.415 (5)	0.4111 (7)	0.046 (4)	0.50
H16E	0.5563	0.2642	0.4168	0.055*	0.50
C21E	0.6195 (9)	0.655 (2)	0.5451 (3)	0.034 (3)	0.50
C22E	0.6612 (8)	0.843 (3)	0.5657 (3)	0.047 (3)	0.50
H22E	0.6863	0.9680	0.5528	0.056*	0.50
N23E	0.6697 (8)	0.863 (2)	0.6044 (3)	0.051 (3)	0.50
C24E	0.6376 (17)	0.681 (4)	0.6229 (6)	0.054 (5)	0.50
H24E	0.6455	0.6818	0.6491	0.064*	0.50
C25E	0.588 (2)	0.475 (7)	0.6018 (12)	0.052 (6)	0.50
H25E	0.5586	0.3654	0.6152	0.062*	0.50
C26E	0.5846 (17)	0.440 (4)	0.5677 (6)	0.055 (5)	0.50
H26E	0.5618	0.2909	0.5562	0.066*	0.50
F12G	0.7150 (4)	0.8899 (17)	0.53393 (14)	0.0807 (19)	0.50
O1G	0.604 (3)	0.249 (4)	0.4877 (13)	0.064 (7)	0.50
C1G	0.6125 (11)	0.474 (3)	0.4973 (4)	0.054 (4)	0.50
N1G	0.6164 (6)	0.676 (2)	0.4738 (2)	0.065 (2)	0.50
H1G	0.6233	0.8244	0.4841	0.078*	0.50
C11G	0.6300 (9)	0.544 (3)	0.5385 (4)	0.057 (4)	0.50
C12G	0.6729 (9)	0.733 (3)	0.5549 (3)	0.045 (3)	0.50
C13G	0.6883 (9)	0.794 (3)	0.5930 (4)	0.057 (3)	0.50
H13G	0.7217	0.9295	0.6031	0.069*	0.50
C14G	0.6459 (18)	0.621 (5)	0.6147 (5)	0.060 (5)	0.50
H14G	0.6486	0.6530	0.6404	0.072*	0.50
C15G	0.605 (2)	0.426 (7)	0.6013 (11)	0.051 (6)	0.50
H15G	0.5840	0.3040	0.6163	0.061*	0.50
C16G	0.5935 (16)	0.412 (6)	0.5596 (6)	0.070 (7)	0.50
H16G	0.5553	0.2930	0.5483	0.084*	0.50
C21G	0.6102 (14)	0.665 (3)	0.4340 (4)	0.051 (4)	0.50
C22G	0.6538 (9)	0.845 (3)	0.4177 (4)	0.063 (4)	0.50
H22G	0.6861	0.9567	0.4340	0.076*	0.50
N23G	0.6555 (13)	0.877 (3)	0.3815 (4)	0.073 (5)	0.50
C24G	0.6058 (19)	0.661 (7)	0.3602 (9)	0.071 (7)	0.50
H24G	0.6060	0.6501	0.3343	0.085*	0.50
C25G	0.564 (2)	0.493 (10)	0.3755 (12)	0.068 (8)	0.50
H25G	0.5327	0.3813	0.3589	0.081*	0.50
C26G	0.5583 (12)	0.455 (5)	0.4129 (8)	0.056 (5)	0.50
H26G	0.5288	0.3269	0.4231	0.067*	0.50
F12F	0.2125 (3)	−0.2157 (14)	0.46362 (12)	0.0633 (15)	0.50
O1F	0.093 (2)	0.407 (4)	0.4964 (9)	0.063 (5)	0.50
C1F	0.1132 (16)	0.194 (3)	0.4885 (4)	0.040 (4)	0.50
N1F	0.1216 (5)	−0.0057 (16)	0.51310 (17)	0.0477 (19)	0.50
H1F	0.1282	−0.1563	0.5043	0.057*	0.50
C11F	0.1171 (9)	0.135 (3)	0.4484 (3)	0.053 (3)	0.50
C12F	0.1663 (7)	−0.065 (3)	0.4380 (3)	0.051 (3)	0.50
C13F	0.1714 (8)	−0.117 (3)	0.3990 (3)	0.056 (3)	0.50
H13F	0.2047	−0.2490	0.3922	0.067*	0.50
C14F	0.127 (2)	0.030 (7)	0.3726 (8)	0.078 (8)	0.50
H14F	0.1340	−0.0165	0.3482	0.093*	0.50
C15F	0.071 (2)	0.242 (7)	0.3732 (8)	0.130 (10)	0.50
H15F	0.0439	0.3415	0.3537	0.156*	0.50
C16F	0.071 (2)	0.258 (6)	0.4206 (9)	0.068 (6)	0.50
H16F	0.0316	0.3696	0.4281	0.082*	0.50
C21F	0.1200 (10)	0.020 (3)	0.5523 (3)	0.053 (3)	0.50
C22F	0.0768 (17)	0.264 (7)	0.5690 (7)	0.070 (6)	0.50
H22F	0.0484	0.4050	0.5577	0.084*	0.50
N23F	0.0990 (12)	0.180 (4)	0.6095 (5)	0.074 (5)	0.50
C24F	0.1347 (19)	−0.005 (6)	0.6276 (9)	0.073 (6)	0.50
H24F	0.1369	−0.0091	0.6537	0.087*	0.50
C25F	0.1687 (10)	−0.190 (3)	0.6109 (4)	0.061 (4)	0.50
H25F	0.1952	−0.3263	0.6245	0.073*	0.50
C26F	0.1639 (8)	−0.177 (2)	0.5749 (3)	0.054 (3)	0.50
H26F	0.1906	−0.3034	0.5627	0.065*	0.50
F12H	0.2167 (4)	−0.2108 (17)	0.53712 (14)	0.0795 (19)	0.50
O1H	0.096 (2)	0.420 (4)	0.4897 (9)	0.074 (7)	0.50
C1H	0.1070 (18)	0.199 (4)	0.5009 (4)	0.052 (5)	0.50
N1H	0.1165 (5)	−0.0014 (19)	0.4774 (2)	0.053 (2)	0.50
H1H	0.1233	−0.1510	0.4874	0.064*	0.50
C11H	0.1220 (9)	0.136 (3)	0.5426 (4)	0.058 (3)	0.50
C12H	0.1732 (8)	−0.060 (3)	0.5606 (3)	0.055 (3)	0.50
C13H	0.1876 (9)	−0.110 (3)	0.5993 (4)	0.066 (4)	0.50
H13H	0.2206	−0.2470	0.6090	0.079*	0.50
C14H	0.1517 (15)	0.049 (6)	0.6222 (8)	0.074 (7)	0.50
H14H	0.1632	0.0214	0.6481	0.089*	0.50
C15H	0.0946 (16)	0.267 (5)	0.6084 (7)	0.106 (9)	0.50
H15H	0.0690	0.3911	0.6215	0.128*	0.50
C16H	0.0923 (19)	0.221 (6)	0.5678 (9)	0.077 (7)	0.50
H16H	0.0430	0.2979	0.5566	0.093*	0.50
C21H	0.1160 (10)	0.016 (3)	0.4387 (3)	0.056 (3)	0.50
C22H	0.077 (2)	0.208 (6)	0.4128 (8)	0.064 (6)	0.50
H22H	0.0472	0.3417	0.4219	0.076*	0.50
N23H	0.0818 (14)	0.198 (3)	0.3818 (4)	0.066 (4)	0.50
C24H	0.1253 (18)	−0.025 (6)	0.3641 (8)	0.059 (5)	0.50
H24H	0.1283	−0.0270	0.3384	0.071*	0.50
C25H	0.1557 (8)	−0.198 (3)	0.3842 (3)	0.054 (3)	0.50
H25H	0.1796	−0.3394	0.3743	0.065*	0.50
C26H	0.1533 (7)	−0.177 (2)	0.4207 (4)	0.052 (3)	0.50
H26H	0.1794	−0.3064	0.4360	0.063*	0.50
F22W	0.6211 (16)	0.414 (8)	0.1280 (7)	0.096 (7)*	0.13
O1W	0.728 (4)	−0.243 (10)	0.1790 (14)	0.087 (17)*	0.13
C1W	0.710 (5)	−0.037 (10)	0.1645 (8)	0.090 (12)*	0.13
N1W	0.720 (3)	0.181 (10)	0.1866 (8)	0.089 (9)*	0.13
H1W	0.7232	0.3253	0.1754	0.107*	0.13
C11W	0.727 (3)	0.181 (9)	0.2256 (8)	0.084 (9)*	0.13
C12W	0.686 (2)	0.376 (8)	0.2419 (9)	0.092 (10)*	0.13
H12W	0.6582	0.5037	0.2268	0.110*	0.13
N13W	0.686 (2)	0.380 (9)	0.2807 (10)	0.093 (11)*	0.13
C14W	0.727 (3)	0.190 (10)	0.3032 (7)	0.093 (12)*	0.13
H14W	0.7275	0.1926	0.3292	0.111*	0.13
C15W	0.768 (3)	−0.005 (9)	0.2870 (13)	0.085 (12)*	0.13
H15W	0.7960	−0.1325	0.3020	0.101*	0.13
C16W	0.768 (3)	−0.009 (8)	0.2481 (13)	0.081 (11)*	0.13
H16W	0.7957	−0.1395	0.2372	0.097*	0.13
C21W	0.692 (2)	0.047 (7)	0.1239 (6)	0.067 (9)*	0.13
C22W	0.6505 (18)	0.269 (6)	0.1103 (7)	0.060 (8)*	0.13
C23W	0.6474 (17)	0.337 (6)	0.0726 (8)	0.043 (8)*	0.13
H23W	0.6197	0.4852	0.0636	0.051*	0.13
C24W	0.686 (3)	0.184 (8)	0.0485 (7)	0.063 (12)*	0.13
H24W	0.6837	0.2292	0.0233	0.076*	0.13
C25W	0.727 (3)	−0.038 (7)	0.0621 (9)	0.070 (13)*	0.13
H25W	0.7529	−0.1406	0.0460	0.084*	0.13
C26W	0.730 (2)	−0.106 (6)	0.0998 (9)	0.068 (11)*	0.13
H26W	0.7581	−0.2545	0.1089	0.081*	0.13
F22X	0.1227 (10)	0.279 (4)	0.2033 (4)	0.073 (4)*	0.17
O1X	0.231 (4)	0.901 (8)	0.1761 (14)	0.055 (11)*	0.17
C1X	0.219 (4)	0.678 (8)	0.1819 (8)	0.076 (10)*	0.17
N1X	0.2114 (17)	0.495 (7)	0.1552 (6)	0.081 (7)*	0.17
H1X	0.2059	0.3417	0.1634	0.097*	0.17
C11X	0.211 (2)	0.513 (8)	0.1171 (6)	0.100 (8)*	0.17
C12X	0.1664 (18)	0.331 (7)	0.0941 (8)	0.100 (9)*	0.17
H12X	0.1382	0.2014	0.1048	0.120*	0.17
N13X	0.1636 (18)	0.343 (7)	0.0552 (8)	0.117 (9)*	0.17
C14X	0.206 (2)	0.537 (8)	0.0392 (6)	0.120 (10)*	0.17
H14X	0.2039	0.5454	0.0131	0.144*	0.17
C15X	0.250 (2)	0.719 (7)	0.0622 (10)	0.118 (11)*	0.17
H15X	0.2786	0.8491	0.0515	0.141*	0.17
C16X	0.253 (2)	0.707 (7)	0.1011 (9)	0.109 (10)*	0.17
H16X	0.2831	0.8289	0.1165	0.131*	0.17
C21X	0.215 (2)	0.654 (8)	0.2226 (7)	0.102 (11)*	0.17
C22X	0.166 (2)	0.446 (7)	0.2299 (7)	0.101 (10)*	0.17
C23X	0.1607 (17)	0.376 (6)	0.2669 (9)	0.068 (9)*	0.17
H23X	0.1279	0.2377	0.2718	0.081*	0.17
C24X	0.204 (3)	0.514 (8)	0.2966 (6)	0.091 (13)*	0.17
H24X	0.2009	0.4673	0.3214	0.109*	0.17
C25X	0.253 (3)	0.721 (8)	0.2893 (9)	0.100 (15)*	0.17
H25X	0.2827	0.8134	0.3092	0.120*	0.17
C26X	0.259 (2)	0.791 (7)	0.2523 (11)	0.098 (13)*	0.17
H26X	0.2914	0.9299	0.2474	0.117*	0.17
F22Y	1.0551 (10)	0.886 (5)	0.1231 (4)	0.080 (5)*	0.17
O1Y	0.9538 (16)	0.269 (5)	0.1555 (9)	0.058 (9)*	0.17
C1Y	0.939 (2)	0.488 (5)	0.1435 (6)	0.057 (6)*	0.17
N1Y	0.9452 (15)	0.670 (5)	0.1716 (5)	0.053 (5)*	0.17
H1Y	0.9344	0.8300	0.1682	0.064*	0.17
C11Y	0.9727 (18)	0.550 (5)	0.2073 (5)	0.034 (5)*	0.17
C12Y	1.0197 (14)	0.742 (5)	0.2273 (5)	0.016 (5)*	0.17
H12Y	1.0514	0.8525	0.2148	0.019*	0.17
N13Y	1.0191 (13)	0.768 (5)	0.2659 (5)	0.019 (5)*	0.17
C14Y	0.9716 (19)	0.603 (7)	0.2845 (6)	0.029 (6)*	0.17
H14Y	0.9713	0.6206	0.3103	0.035*	0.17
C15Y	0.925 (2)	0.411 (6)	0.2645 (8)	0.030 (6)*	0.17
H15Y	0.8929	0.3008	0.2770	0.036*	0.17
C16Y	0.925 (2)	0.385 (5)	0.2260 (8)	0.035 (6)*	0.17
H16Y	0.8938	0.2569	0.2126	0.043*	0.17
C21Y	0.9513 (13)	0.604 (5)	0.1054 (5)	0.018 (6)*	0.17
C22Y	1.0102 (11)	0.777 (5)	0.0960 (5)	0.040 (6)*	0.17
C23Y	1.0135 (15)	0.835 (6)	0.0584 (6)	0.059 (9)*	0.17
H23Y	1.0529	0.9501	0.0521	0.071*	0.17
C24Y	0.9578 (19)	0.720 (8)	0.0301 (4)	0.046 (12)*	0.17
H24Y	0.9600	0.7581	0.0049	0.056*	0.17
C25Y	0.8989 (19)	0.547 (8)	0.0395 (6)	0.039 (10)*	0.17
H25Y	0.8616	0.4699	0.0206	0.047*	0.17
C26Y	0.8956 (15)	0.489 (6)	0.0772 (7)	0.035 (9)*	0.17
H26Y	0.8562	0.3737	0.0834	0.042*	0.17
F22Z	0.5572 (15)	−0.196 (7)	0.2006 (6)	0.092 (7)*	0.13
O1Z	0.412 (3)	0.398 (7)	0.1594 (12)	0.033 (8)*	0.13
C1Z	0.435 (3)	0.182 (8)	0.1668 (8)	0.052 (9)*	0.13
N1Z	0.4546 (19)	0.015 (7)	0.1403 (6)	0.062 (6)*	0.13
H1Z	0.4669	−0.1374	0.1484	0.074*	0.13
C11Z	0.457 (3)	0.054 (8)	0.1028 (6)	0.055 (7)*	0.13
C12Z	0.486 (2)	−0.151 (7)	0.0837 (8)	0.060 (8)*	0.13
H12Z	0.5084	−0.2941	0.0970	0.072*	0.13
N13Z	0.4818 (19)	−0.143 (7)	0.0447 (8)	0.068 (8)*	0.13
C14Z	0.449 (3)	0.070 (9)	0.0247 (6)	0.063 (10)*	0.13
H14Z	0.4457	0.0757	−0.0014	0.075*	0.13
C15Z	0.420 (3)	0.276 (8)	0.0438 (11)	0.065 (10)*	0.13
H15Z	0.3974	0.4185	0.0304	0.079*	0.13
C16Z	0.424 (3)	0.268 (7)	0.0828 (11)	0.063 (10)*	0.13
H16Z	0.4045	0.4050	0.0956	0.075*	0.13
C21Z	0.449 (5)	0.144 (19)	0.2090 (10)	0.20 (3)*	0.13
C22Z	0.517 (5)	−0.015 (16)	0.221 (2)	0.21 (3)*	0.13
C23Z	0.546 (3)	−0.043 (13)	0.259 (2)	0.21 (3)*	0.13
H23Z	0.5911	−0.1495	0.2667	0.258*	0.13
C24Z	0.508 (5)	0.089 (17)	0.2854 (11)	0.21 (3)*	0.13
H24Z	0.5275	0.0706	0.3110	0.252*	0.13
C25Z	0.440 (5)	0.248 (15)	0.2738 (19)	0.21 (3)*	0.13
H25Z	0.4148	0.3367	0.2915	0.249*	0.13
C26Z	0.411 (4)	0.276 (15)	0.236 (2)	0.21 (3)*	0.13
H26Z	0.3658	0.3827	0.2277	0.247*	0.13

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F12A	0.0686 (18)	0.064 (3)	0.0654 (16)	0.024 (2)	0.0162 (13)	0.0040 (18)
O1A	0.097 (4)	0.037 (3)	0.051 (3)	0.016 (3)	0.016 (3)	−0.005 (2)
C1A	0.059 (4)	0.040 (4)	0.056 (3)	−0.005 (3)	0.012 (3)	−0.003 (3)
N1A	0.061 (3)	0.043 (3)	0.044 (2)	0.008 (2)	0.0128 (17)	−0.005 (2)
C11A	0.049 (3)	0.039 (4)	0.043 (2)	0.004 (3)	0.0024 (19)	0.014 (3)
C12A	0.060 (3)	0.028 (3)	0.047 (2)	−0.003 (3)	0.003 (2)	0.008 (2)
C13A	0.061 (3)	0.050 (4)	0.066 (3)	0.005 (3)	0.021 (3)	0.007 (3)
C14A	0.107 (5)	0.063 (5)	0.048 (3)	−0.003 (5)	0.016 (3)	−0.004 (3)
C15A	0.076 (5)	0.078 (6)	0.058 (3)	0.013 (5)	0.001 (3)	0.035 (4)
C16A	0.065 (3)	0.036 (4)	0.062 (3)	0.010 (3)	0.006 (2)	0.005 (3)
C21A	0.039 (2)	0.024 (3)	0.047 (2)	0.000 (2)	0.0104 (19)	−0.006 (2)
C22A	0.067 (3)	0.056 (5)	0.050 (3)	0.006 (3)	0.012 (3)	−0.021 (3)
N23A	0.088 (3)	0.042 (3)	0.039 (2)	0.001 (3)	0.007 (2)	−0.002 (2)
C24A	0.098 (5)	0.058 (5)	0.043 (3)	−0.016 (4)	0.021 (3)	−0.009 (3)
C25A	0.079 (4)	0.040 (4)	0.061 (3)	−0.007 (4)	0.027 (3)	−0.020 (3)
C26A	0.057 (3)	0.025 (3)	0.059 (3)	0.005 (3)	0.015 (2)	−0.007 (2)
F12B	0.078 (2)	0.063 (2)	0.0469 (14)	−0.025 (2)	0.0041 (13)	0.0053 (16)
O1B	0.085 (5)	0.033 (3)	0.059 (4)	−0.001 (3)	−0.001 (3)	−0.002 (3)
C1B	0.050 (3)	0.023 (4)	0.046 (3)	−0.012 (3)	0.003 (3)	0.001 (3)
N1B	0.068 (3)	0.024 (3)	0.034 (2)	−0.003 (2)	0.0023 (18)	−0.005 (2)
C11B	0.051 (3)	0.023 (3)	0.040 (2)	0.006 (2)	0.003 (2)	0.000 (2)
C12B	0.053 (3)	0.039 (4)	0.054 (3)	−0.002 (3)	0.008 (2)	0.008 (3)
C13B	0.069 (3)	0.046 (4)	0.043 (3)	−0.003 (3)	−0.001 (2)	−0.008 (3)
C14B	0.077 (4)	0.042 (4)	0.037 (2)	−0.004 (3)	0.007 (2)	−0.004 (3)
C15B	0.080 (4)	0.067 (5)	0.053 (3)	0.002 (4)	0.028 (3)	0.013 (3)
C16B	0.055 (3)	0.044 (4)	0.047 (2)	−0.004 (3)	0.014 (2)	−0.001 (3)
C21B	0.054 (3)	0.042 (4)	0.044 (3)	−0.007 (3)	0.017 (2)	−0.004 (3)
C22B	0.072 (4)	0.031 (3)	0.039 (3)	0.003 (3)	0.015 (2)	0.005 (2)
N23B	0.077 (3)	0.061 (4)	0.043 (2)	0.012 (3)	0.017 (2)	0.009 (3)
C24B	0.076 (4)	0.049 (4)	0.045 (3)	0.014 (3)	0.013 (3)	0.005 (3)
C25B	0.075 (4)	0.059 (5)	0.050 (3)	0.000 (4)	0.001 (3)	−0.013 (3)
C26B	0.060 (3)	0.033 (4)	0.049 (3)	−0.015 (3)	0.011 (2)	−0.007 (3)
F12C	0.083 (2)	0.059 (2)	0.0535 (15)	−0.028 (2)	0.0021 (14)	0.0036 (17)
O1C	0.070 (4)	0.037 (3)	0.054 (3)	−0.017 (3)	0.012 (2)	−0.0036 (19)
C1C	0.052 (3)	0.046 (5)	0.053 (3)	0.008 (3)	0.019 (3)	−0.001 (3)
N1C	0.069 (3)	0.031 (3)	0.044 (2)	−0.002 (2)	0.0184 (19)	−0.002 (2)
C11C	0.036 (4)	0.079 (6)	0.044 (3)	−0.013 (4)	0.007 (2)	0.009 (3)
C12C	0.049 (4)	0.082 (6)	0.057 (4)	−0.003 (4)	−0.003 (3)	0.032 (4)
C13C	0.107 (7)	0.071 (8)	0.081 (5)	0.013 (6)	−0.016 (4)	0.039 (5)
C14C	0.102 (7)	0.067 (7)	0.047 (3)	0.012 (5)	0.010 (3)	0.000 (4)
C15C	0.087 (6)	0.053 (6)	0.052 (4)	0.002 (4)	0.024 (4)	0.015 (4)
C16C	0.076 (4)	0.061 (5)	0.060 (5)	−0.012 (4)	0.023 (3)	−0.002 (4)
C21C	0.055 (4)	0.022 (3)	0.044 (3)	0.013 (3)	−0.005 (2)	−0.003 (2)
C22C	0.057 (3)	0.045 (4)	0.048 (3)	−0.007 (3)	−0.002 (2)	−0.015 (3)
N23C	0.085 (4)	0.036 (3)	0.045 (2)	−0.003 (3)	0.014 (2)	−0.001 (2)
C24C	0.115 (8)	0.063 (6)	0.037 (3)	0.005 (5)	0.013 (3)	−0.005 (3)
C25C	0.065 (5)	0.047 (5)	0.053 (4)	0.006 (4)	−0.008 (3)	−0.019 (3)
C26C	0.060 (4)	0.073 (6)	0.052 (4)	0.003 (4)	−0.007 (3)	0.003 (3)
F12D	0.0782 (19)	0.076 (3)	0.0582 (15)	0.034 (2)	0.0142 (14)	0.0043 (18)
O1D	0.092 (6)	0.035 (4)	0.083 (4)	−0.006 (3)	0.021 (3)	−0.001 (3)
C1D	0.046 (3)	0.029 (4)	0.056 (3)	0.004 (3)	0.006 (2)	0.002 (3)
N1D	0.064 (3)	0.023 (3)	0.055 (2)	−0.005 (2)	0.0151 (19)	−0.004 (2)
C11D	0.048 (3)	0.025 (3)	0.061 (3)	−0.008 (2)	0.015 (2)	−0.005 (3)
C12D	0.045 (3)	0.052 (4)	0.063 (3)	0.002 (3)	0.015 (3)	0.002 (3)
C13D	0.066 (3)	0.057 (4)	0.051 (3)	−0.014 (3)	0.020 (3)	−0.006 (3)
C14D	0.089 (4)	0.066 (6)	0.047 (3)	−0.011 (5)	0.007 (3)	0.016 (4)
C15D	0.089 (5)	0.073 (6)	0.065 (4)	−0.007 (5)	−0.001 (3)	0.020 (4)
C16D	0.067 (5)	0.063 (5)	0.072 (4)	0.006 (4)	0.008 (3)	0.021 (4)
C21D	0.045 (3)	0.062 (4)	0.047 (2)	−0.015 (3)	0.008 (2)	−0.010 (3)
C22D	0.063 (3)	0.033 (3)	0.055 (3)	0.004 (3)	0.008 (2)	−0.005 (2)
N23D	0.071 (3)	0.060 (4)	0.063 (3)	−0.001 (3)	0.005 (2)	−0.006 (3)
C24D	0.060 (3)	0.051 (4)	0.051 (3)	0.000 (3)	0.001 (2)	−0.014 (3)
C25D	0.060 (3)	0.061 (5)	0.057 (3)	0.001 (3)	0.022 (2)	−0.017 (3)
C26D	0.043 (3)	0.056 (4)	0.049 (2)	−0.004 (3)	0.012 (2)	−0.007 (3)
F12E	0.070 (3)	0.074 (4)	0.049 (2)	−0.031 (3)	0.016 (2)	−0.014 (3)
O1E	0.083 (16)	0.036 (9)	0.060 (8)	−0.026 (9)	0.017 (8)	−0.005 (7)
C1E	0.056 (6)	0.050 (9)	0.040 (6)	−0.001 (5)	0.006 (6)	0.006 (6)
N1E	0.081 (5)	0.038 (6)	0.032 (4)	−0.009 (4)	0.013 (3)	0.006 (4)
C11E	0.047 (7)	0.054 (10)	0.031 (5)	0.000 (7)	−0.004 (4)	−0.001 (6)
C12E	0.062 (7)	0.046 (7)	0.026 (6)	0.013 (6)	0.009 (5)	0.011 (4)
C13E	0.080 (10)	0.078 (13)	0.059 (10)	−0.015 (9)	0.014 (8)	0.003 (8)
C14E	0.055 (12)	0.082 (13)	0.047 (8)	−0.016 (8)	0.015 (8)	0.000 (8)
C15E	0.063 (16)	0.070 (11)	0.045 (8)	0.006 (11)	0.008 (9)	−0.027 (7)
C16E	0.029 (9)	0.060 (9)	0.050 (6)	0.011 (7)	0.009 (7)	−0.009 (6)
C21E	0.044 (7)	0.017 (6)	0.043 (5)	−0.002 (5)	0.012 (5)	0.009 (4)
C22E	0.063 (7)	0.044 (8)	0.033 (6)	−0.013 (6)	0.006 (5)	0.009 (5)
N23E	0.077 (7)	0.047 (7)	0.030 (5)	0.002 (5)	0.007 (4)	0.002 (4)
C24E	0.080 (9)	0.053 (11)	0.033 (7)	−0.006 (9)	0.023 (5)	−0.004 (6)
C25E	0.059 (13)	0.042 (12)	0.060 (9)	0.011 (10)	0.029 (10)	0.019 (8)
C26E	0.070 (8)	0.044 (7)	0.060 (11)	−0.023 (6)	0.042 (8)	0.004 (7)
F12G	0.094 (4)	0.080 (5)	0.065 (3)	−0.038 (4)	0.000 (3)	0.002 (3)
O1G	0.083 (17)	0.038 (8)	0.071 (10)	−0.003 (6)	0.007 (9)	0.001 (7)
C1G	0.055 (7)	0.049 (9)	0.061 (8)	0.018 (6)	0.015 (8)	0.003 (7)
N1G	0.076 (6)	0.051 (7)	0.070 (6)	−0.006 (5)	0.018 (4)	−0.001 (5)
C11G	0.041 (6)	0.073 (11)	0.057 (6)	−0.002 (7)	0.005 (5)	0.009 (7)
C12G	0.052 (7)	0.045 (8)	0.038 (6)	0.003 (6)	0.006 (5)	0.003 (5)
C13G	0.057 (7)	0.057 (9)	0.056 (9)	0.001 (6)	0.000 (6)	0.010 (7)
C14G	0.086 (10)	0.060 (12)	0.036 (9)	0.030 (8)	0.010 (7)	0.001 (7)
C15G	0.053 (11)	0.048 (13)	0.050 (9)	0.014 (9)	0.003 (7)	0.015 (8)
C16G	0.060 (10)	0.121 (15)	0.031 (7)	−0.003 (9)	0.008 (7)	−0.001 (8)
C21G	0.061 (8)	0.052 (10)	0.039 (6)	0.022 (8)	0.001 (6)	0.000 (6)
C22G	0.082 (8)	0.067 (10)	0.040 (7)	−0.022 (8)	0.005 (6)	−0.016 (7)
N23G	0.103 (11)	0.063 (10)	0.057 (9)	−0.019 (8)	0.021 (7)	−0.025 (7)
C24G	0.068 (16)	0.078 (12)	0.062 (8)	0.001 (10)	−0.006 (8)	−0.046 (8)
C25G	0.056 (14)	0.083 (14)	0.065 (10)	−0.005 (11)	0.014 (9)	−0.024 (10)
C26G	0.030 (10)	0.074 (10)	0.062 (7)	0.020 (8)	0.003 (7)	−0.018 (6)
F12F	0.077 (3)	0.070 (4)	0.046 (2)	0.029 (3)	0.020 (2)	0.013 (3)
O1F	0.091 (9)	0.027 (8)	0.076 (9)	0.014 (6)	0.033 (7)	0.001 (6)
C1F	0.041 (7)	0.021 (9)	0.059 (7)	0.003 (5)	0.011 (8)	0.004 (6)
N1F	0.082 (5)	0.023 (5)	0.041 (4)	0.004 (4)	0.016 (3)	−0.005 (3)
C11F	0.061 (7)	0.044 (8)	0.060 (6)	−0.005 (6)	0.026 (5)	−0.008 (6)
C12F	0.041 (5)	0.068 (8)	0.048 (6)	−0.005 (6)	0.023 (5)	−0.012 (5)
C13F	0.082 (7)	0.058 (8)	0.034 (7)	−0.015 (7)	0.025 (6)	−0.009 (6)
C14F	0.106 (13)	0.084 (18)	0.048 (10)	−0.007 (12)	0.030 (8)	0.008 (10)
C15F	0.130 (17)	0.16 (2)	0.104 (14)	0.012 (13)	0.037 (14)	0.016 (14)
C16F	0.075 (10)	0.079 (15)	0.056 (9)	0.000 (10)	0.026 (7)	0.013 (9)
C21F	0.062 (8)	0.050 (9)	0.050 (6)	−0.011 (8)	0.018 (6)	−0.012 (6)
C22F	0.060 (14)	0.100 (11)	0.052 (7)	0.017 (9)	0.012 (8)	−0.045 (7)
N23F	0.088 (10)	0.069 (10)	0.078 (7)	−0.011 (7)	0.055 (7)	−0.036 (6)
C24F	0.083 (14)	0.062 (11)	0.072 (9)	−0.018 (8)	0.008 (8)	−0.005 (7)
C25F	0.074 (8)	0.053 (8)	0.057 (8)	0.002 (6)	0.015 (5)	0.006 (6)
C26F	0.092 (8)	0.020 (5)	0.053 (6)	0.007 (5)	0.024 (6)	0.008 (5)
F12H	0.088 (4)	0.082 (5)	0.066 (3)	0.031 (4)	0.002 (3)	−0.007 (3)
O1H	0.090 (11)	0.046 (10)	0.084 (12)	−0.017 (7)	0.003 (8)	0.014 (6)
C1H	0.046 (7)	0.041 (12)	0.071 (8)	0.007 (6)	0.021 (9)	−0.017 (7)
N1H	0.074 (5)	0.030 (5)	0.054 (5)	0.001 (4)	0.004 (3)	0.005 (4)
C11H	0.054 (6)	0.038 (8)	0.085 (7)	−0.022 (6)	0.018 (6)	−0.002 (6)
C12H	0.054 (6)	0.057 (8)	0.056 (6)	−0.004 (7)	0.009 (5)	−0.008 (6)
C13H	0.073 (8)	0.067 (10)	0.056 (8)	0.011 (7)	−0.001 (6)	−0.019 (7)
C14H	0.056 (10)	0.083 (16)	0.079 (11)	0.029 (12)	−0.012 (8)	−0.021 (10)
C15H	0.121 (14)	0.083 (16)	0.102 (10)	0.019 (11)	−0.029 (9)	−0.004 (10)
C16H	0.039 (8)	0.112 (17)	0.090 (10)	0.016 (9)	0.038 (7)	−0.013 (11)
C21H	0.052 (7)	0.057 (9)	0.062 (7)	0.011 (8)	0.024 (6)	0.000 (6)
C22H	0.079 (9)	0.054 (10)	0.062 (13)	0.040 (8)	0.026 (9)	0.020 (9)
N23H	0.090 (8)	0.057 (7)	0.046 (6)	−0.004 (6)	−0.002 (5)	0.027 (6)
C24H	0.060 (8)	0.052 (11)	0.071 (12)	0.002 (7)	0.029 (8)	0.005 (9)
C25H	0.067 (7)	0.050 (8)	0.048 (7)	−0.002 (6)	0.018 (5)	−0.008 (6)
C26H	0.073 (7)	0.038 (6)	0.049 (6)	0.007 (5)	0.018 (5)	−0.006 (5)

Geometric parameters (Å, º)

F12A—C12A	1.364 (6)	F12F—C12F	1.350 (14)
O1A—C1A	1.249 (9)	O1F—C1F	1.206 (16)
C1A—N1A	1.339 (8)	C1F—N1F	1.361 (14)
C1A—C11A	1.533 (8)	C1F—C11F	1.478 (15)
N1A—C21A	1.387 (5)	N1F—C21F	1.413 (12)
N1A—H1A	0.8600	N1F—H1F	0.8600
C11A—C12A	1.364 (8)	C11F—C16F	1.32 (4)
C11A—C16A	1.423 (8)	C11F—C12F	1.396 (19)
C12A—C13A	1.355 (7)	C12F—C13F	1.437 (14)
C13A—C14A	1.438 (9)	C13F—C14F	1.34 (4)
C13A—H13A	0.9300	C13F—H13F	0.9300
C14A—C15A	1.337 (10)	C14F—C15F	1.43 (5)
C14A—H14A	0.9300	C14F—H14F	0.9300
C15A—C16A	1.395 (7)	C15F—C16F	1.70 (4)
C15A—H15A	0.9300	C15F—H15F	0.9300
C16A—H16A	0.9300	C16F—H16F	0.9300
C21A—C22A	1.359 (8)	C21F—C26F	1.435 (19)
C21A—C26A	1.411 (7)	C21F—C22F	1.61 (3)
C22A—N23A	1.368 (6)	C22F—N23F	1.51 (3)
C22A—H22A	0.9300	C22F—H22F	0.9300
N23A—C24A	1.339 (9)	N23F—C24F	1.26 (4)
C24A—C25A	1.404 (10)	C24F—C25F	1.30 (4)
C24A—H24A	0.9300	C24F—H24F	0.9300
C25A—C26A	1.346 (7)	C25F—C26F	1.284 (18)
C25A—H25A	0.9300	C25F—H25F	0.9300
C26A—H26A	0.9300	C26F—H26F	0.9300
F12B—C12B	1.355 (7)	F12H—C12H	1.412 (14)
O1B—C1B	1.231 (10)	O1H—C1H	1.227 (18)
C1B—N1B	1.352 (8)	C1H—N1H	1.365 (15)
C1B—C11B	1.491 (7)	C1H—C11H	1.514 (16)
N1B—C21B	1.411 (6)	N1H—C21H	1.386 (12)
N1B—H1B	0.8600	N1H—H1H	0.8600
C11B—C16B	1.369 (8)	C11H—C16H	1.17 (3)
C11B—C12B	1.427 (8)	C11H—C12H	1.41 (2)
C12B—C13B	1.371 (7)	C12H—C13H	1.396 (18)
C13B—C14B	1.370 (9)	C13H—C14H	1.36 (3)
C13B—H13B	0.9300	C13H—H13H	0.9300
C14B—C15B	1.366 (10)	C14H—C15H	1.51 (3)
C14B—H14B	0.9300	C14H—H14H	0.9300
C15B—C16B	1.397 (7)	C15H—C16H	1.47 (4)
C15B—H15B	0.9300	C15H—H15H	0.9300
C16B—H16B	0.9300	C16H—H16H	0.9300
C21B—C26B	1.344 (8)	C21H—C26H	1.385 (17)
C21B—C22B	1.398 (8)	C21H—C22H	1.45 (3)
C22B—N23B	1.344 (6)	C22H—N23H	1.13 (3)
C22B—H22B	0.9300	C22H—H22H	0.9300
N23B—C24B	1.250 (9)	N23H—C24H	1.54 (3)
C24B—C25B	1.432 (10)	C24H—C25H	1.21 (3)
C24B—H24B	0.9300	C24H—H24H	0.9300
C25B—C26B	1.360 (7)	C25H—C26H	1.317 (16)
C25B—H25B	0.9300	C25H—H25H	0.9300
C26B—H26B	0.9300	C26H—H26H	0.9300
F12C—C12C	1.367 (8)	F22W—C22W	1.14 (4)
O1C—C1C	1.236 (10)	O1W—C1W	1.21 (2)
C1C—N1C	1.360 (8)	C1W—N1W	1.38 (2)
C1C—C11C	1.548 (8)	C1W—C21W	1.51 (2)
N1C—C21C	1.417 (6)	N1W—C11W	1.38 (2)
N1C—H1C	0.8600	N1W—H1W	0.8600
C11C—C12C	1.314 (10)	C11W—C12W	1.3900
C11C—C16C	1.415 (9)	C11W—C16W	1.3900
C12C—C13C	1.423 (9)	C12W—N13W	1.3900
C13C—C14C	1.350 (12)	C12W—H12W	0.9300
C13C—H13C	0.9300	N13W—C14W	1.3900
C14C—C15C	1.400 (11)	C14W—C15W	1.3900
C14C—H14C	0.9300	C14W—H14W	0.9300
C15C—C16C	1.358 (8)	C15W—C16W	1.3900
C15C—H15C	0.9300	C15W—H15W	0.9300
C16C—H16C	0.9300	C16W—H16W	0.9300
C21C—C22C	1.356 (9)	C21W—C22W	1.3900
C21C—C26C	1.409 (11)	C21W—C26W	1.3900
C22C—N23C	1.326 (6)	C22W—C23W	1.3900
C22C—H22C	0.9300	C23W—C24W	1.3900
N23C—C24C	1.409 (11)	C23W—H23W	0.9300
C24C—C25C	1.292 (10)	C24W—C25W	1.3900
C24C—H24C	0.9300	C24W—H24W	0.9300
C25C—C26C	1.413 (7)	C25W—C26W	1.3900
C25C—H25C	0.9300	C25W—H25W	0.9300
C26C—H26C	0.9300	C26W—H26W	0.9300
F12D—C12D	1.365 (7)	F22X—C22X	1.40 (3)
O1D—C1D	1.212 (9)	O1X—C1X	1.20 (2)
C1D—N1D	1.372 (8)	C1X—N1X	1.349 (19)
C1D—C11D	1.468 (7)	C1X—C21X	1.47 (2)
N1D—C21D	1.406 (6)	N1X—C11X	1.368 (18)
N1D—H1D	0.8600	N1X—H1X	0.8600
C11D—C16D	1.370 (8)	C11X—C12X	1.3900
C11D—C12D	1.414 (9)	C11X—C16X	1.3900
C12D—C13D	1.378 (7)	C12X—N13X	1.3900
C13D—C14D	1.283 (9)	C12X—H12X	0.9300
C13D—H13D	0.9300	N13X—C14X	1.3900
C14D—C15D	1.421 (12)	C14X—C15X	1.3900
C14D—H14D	0.9300	C14X—H14X	0.9300
C15D—C16D	1.376 (8)	C15X—C16X	1.3900
C15D—H15D	0.9300	C15X—H15X	0.9300
C16D—H16D	0.9300	C16X—H16X	0.9300
C21D—C26D	1.353 (8)	C21X—C22X	1.3900
C21D—C22D	1.423 (8)	C21X—C26X	1.3900
C22D—N23D	1.316 (6)	C22X—C23X	1.3900
C22D—H22D	0.9300	C23X—C24X	1.3900
N23D—C24D	1.332 (8)	C23X—H23X	0.9300
C24D—C25D	1.318 (9)	C24X—C25X	1.3900
C24D—H24D	0.9300	C24X—H24X	0.9300
C25D—C26D	1.418 (6)	C25X—C26X	1.3900
C25D—H25D	0.9300	C25X—H25X	0.9300
C26D—H26D	0.9300	C26X—H26X	0.9300
F12E—C12E	1.343 (15)	F22Y—C22Y	1.26 (2)
O1E—C1E	1.226 (19)	O1Y—C1Y	1.235 (19)
C1E—N1E	1.361 (14)	C1Y—N1Y	1.375 (19)
C1E—C11E	1.538 (14)	C1Y—C21Y	1.535 (18)
N1E—C21E	1.396 (12)	N1Y—C11Y	1.436 (19)
N1E—H1E	0.8600	N1Y—H1Y	0.8600
C11E—C12E	1.28 (2)	C11Y—C12Y	1.3900
C11E—C16E	1.38 (3)	C11Y—C16Y	1.3900
C12E—C13E	1.41 (2)	C12Y—N13Y	1.3900
C13E—C14E	1.39 (4)	C12Y—H12Y	0.9300
C13E—H13E	0.9300	N13Y—C14Y	1.3900
C14E—C15E	1.33 (6)	C14Y—C15Y	1.3900
C14E—H14E	0.9300	C14Y—H14Y	0.9300
C15E—C16E	1.44 (5)	C15Y—C16Y	1.3900
C15E—H15E	0.9300	C15Y—H15Y	0.9300
C16E—H16E	0.9300	C16Y—H16Y	0.9300
C21E—C22E	1.346 (18)	C21Y—C22Y	1.3900
C21E—C26E	1.54 (2)	C21Y—C26Y	1.3900
C22E—N23E	1.378 (15)	C22Y—C23Y	1.3900
C22E—H22E	0.9300	C23Y—C24Y	1.3900
N23E—C24E	1.31 (3)	C23Y—H23Y	0.9300
C24E—C25E	1.48 (5)	C24Y—C25Y	1.3900
C24E—H24E	0.9300	C24Y—H24Y	0.9300
C25E—C26E	1.23 (5)	C25Y—C26Y	1.3900
C25E—H25E	0.9300	C25Y—H25Y	0.9300
C26E—H26E	0.9300	C26Y—H26Y	0.9300
F12G—C12G	1.360 (15)	F22Z—C22Z	1.41 (6)
O1G—C1G	1.23 (2)	O1Z—C1Z	1.21 (2)
C1G—N1G	1.355 (14)	C1Z—N1Z	1.36 (2)
C1G—C11G	1.506 (15)	C1Z—C21Z	1.51 (2)
N1G—C21G	1.414 (14)	N1Z—C11Z	1.368 (19)
N1G—H1G	0.8600	N1Z—H1Z	0.8600
C11G—C16G	1.24 (3)	C11Z—C12Z	1.3900
C11G—C12G	1.30 (2)	C11Z—C16Z	1.3900
C12G—C13G	1.391 (18)	C12Z—N13Z	1.3900
C13G—C14G	1.43 (3)	C12Z—H12Z	0.9300
C13G—H13G	0.9300	N13Z—C14Z	1.3900
C14G—C15G	1.27 (5)	C14Z—C15Z	1.3900
C14G—H14G	0.9300	C14Z—H14Z	0.9300
C15G—C16G	1.48 (5)	C15Z—C16Z	1.3900
C15G—H15G	0.9300	C15Z—H15Z	0.9300
C16G—H16G	0.9300	C16Z—H16Z	0.9300
C21G—C22G	1.35 (3)	C21Z—C22Z	1.3900
C21G—C26G	1.52 (3)	C21Z—C26Z	1.3900
C22G—N23G	1.31 (2)	C22Z—C23Z	1.3900
C22G—H22G	0.9300	C23Z—C24Z	1.3900
N23G—C24G	1.52 (3)	C23Z—H23Z	0.9300
C24G—C25G	1.28 (6)	C24Z—C25Z	1.3900
C24G—H24G	0.9300	C24Z—H24Z	0.9300
C25G—C26G	1.37 (5)	C25Z—C26Z	1.3900
C25G—H25G	0.9300	C25Z—H25Z	0.9300
C26G—H26G	0.9300	C26Z—H26Z	0.9300
O1A—C1A—N1A	122.2 (6)	O1F—C1F—N1F	124.0 (19)
O1A—C1A—C11A	121.9 (6)	O1F—C1F—C11F	118.3 (18)
N1A—C1A—C11A	115.9 (6)	N1F—C1F—C11F	117.0 (13)
C1A—N1A—C21A	128.7 (5)	C1F—N1F—C21F	123.7 (11)
C1A—N1A—H1A	115.7	C1F—N1F—H1F	118.1
C21A—N1A—H1A	115.7	C21F—N1F—H1F	118.1
C12A—C11A—C16A	117.6 (4)	C16F—C11F—C12F	116.4 (15)
C12A—C11A—C1A	127.1 (5)	C16F—C11F—C1F	121.9 (18)
C16A—C11A—C1A	114.9 (5)	C12F—C11F—C1F	121.5 (13)
C13A—C12A—C11A	125.7 (5)	F12F—C12F—C11F	122.4 (10)
C13A—C12A—F12A	117.0 (5)	F12F—C12F—C13F	116.4 (13)
C11A—C12A—F12A	117.3 (4)	C11F—C12F—C13F	121.2 (12)
C12A—C13A—C14A	115.8 (6)	C14F—C13F—C12F	118.4 (17)
C12A—C13A—H13A	122.1	C14F—C13F—H13F	120.8
C14A—C13A—H13A	122.1	C12F—C13F—H13F	120.8
C15A—C14A—C13A	120.1 (5)	C13F—C14F—C15F	135 (2)
C15A—C14A—H14A	119.9	C13F—C14F—H14F	112.6
C13A—C14A—H14A	119.9	C15F—C14F—H14F	112.6
C14A—C15A—C16A	123.1 (6)	C14F—C15F—C16F	99 (2)
C14A—C15A—H15A	118.5	C14F—C15F—H15F	130.7
C16A—C15A—H15A	118.5	C16F—C15F—H15F	130.7
C15A—C16A—C11A	117.4 (6)	C11F—C16F—C15F	130 (2)
C15A—C16A—H16A	121.3	C11F—C16F—H16F	115.0
C11A—C16A—H16A	121.3	C15F—C16F—H16F	115.0
C22A—C21A—N1A	117.1 (5)	N1F—C21F—C26F	114.3 (13)
C22A—C21A—C26A	117.8 (4)	N1F—C21F—C22F	121.1 (16)
N1A—C21A—C26A	125.0 (5)	C26F—C21F—C22F	124.5 (14)
C21A—C22A—N23A	124.5 (5)	N23F—C22F—C21F	94 (2)
C21A—C22A—H22A	117.8	N23F—C22F—H22F	132.9
N23A—C22A—H22A	117.8	C21F—C22F—H22F	132.9
C24A—N23A—C22A	115.6 (6)	C24F—N23F—C22F	138 (2)
N23A—C24A—C25A	123.8 (5)	N23F—C24F—C25F	122 (3)
N23A—C24A—H24A	118.1	N23F—C24F—H24F	119.0
C25A—C24A—H24A	118.1	C25F—C24F—H24F	119.0
C26A—C25A—C24A	118.7 (6)	C26F—C25F—C24F	117.0 (19)
C26A—C25A—H25A	120.6	C26F—C25F—H25F	121.5
C24A—C25A—H25A	120.6	C24F—C25F—H25F	121.5
C25A—C26A—C21A	119.6 (5)	C25F—C26F—C21F	123.9 (12)
C25A—C26A—H26A	120.2	C25F—C26F—H26F	118.1
C21A—C26A—H26A	120.2	C21F—C26F—H26F	118.1
O1B—C1B—N1B	122.1 (7)	O1H—C1H—N1H	123.0 (19)
O1B—C1B—C11B	120.6 (7)	O1H—C1H—C11H	121 (2)
N1B—C1B—C11B	117.2 (5)	N1H—C1H—C11H	115.4 (14)
C1B—N1B—C21B	126.0 (5)	C1H—N1H—C21H	125.5 (12)
C1B—N1B—H1B	117.0	C1H—N1H—H1H	117.3
C21B—N1B—H1B	117.0	C21H—N1H—H1H	117.3
C16B—C11B—C12B	116.1 (4)	C16H—C11H—C12H	102 (2)
C16B—C11B—C1B	120.1 (5)	C16H—C11H—C1H	131 (2)
C12B—C11B—C1B	123.6 (5)	C12H—C11H—C1H	127.2 (14)
F12B—C12B—C13B	118.6 (5)	C13H—C12H—F12H	117.5 (14)
F12B—C12B—C11B	119.2 (4)	C13H—C12H—C11H	126.0 (13)
C13B—C12B—C11B	122.2 (5)	F12H—C12H—C11H	116.4 (10)
C14B—C13B—C12B	119.2 (6)	C14H—C13H—C12H	117.6 (17)
C14B—C13B—H13B	120.4	C14H—C13H—H13H	121.2
C12B—C13B—H13B	120.4	C12H—C13H—H13H	121.2
C15B—C14B—C13B	120.6 (5)	C13H—C14H—C15H	124 (2)
C15B—C14B—H14B	119.7	C13H—C14H—H14H	117.9
C13B—C14B—H14B	119.7	C15H—C14H—H14H	117.9
C14B—C15B—C16B	119.9 (6)	C16H—C15H—C14H	97 (2)
C14B—C15B—H15B	120.0	C16H—C15H—H15H	131.3
C16B—C15B—H15B	120.0	C14H—C15H—H15H	131.3
C11B—C16B—C15B	121.8 (6)	C11H—C16H—C15H	151 (3)
C11B—C16B—H16B	119.1	C11H—C16H—H16H	104.7
C15B—C16B—H16B	119.1	C15H—C16H—H16H	104.7
C26B—C21B—C22B	117.3 (5)	C26H—C21H—N1H	118.5 (13)
C26B—C21B—N1B	127.3 (5)	C26H—C21H—C22H	112.8 (12)
C22B—C21B—N1B	115.2 (5)	N1H—C21H—C22H	128.5 (15)
N23B—C22B—C21B	123.2 (6)	N23H—C22H—C21H	121 (2)
N23B—C22B—H22B	118.4	N23H—C22H—H22H	119.7
C21B—C22B—H22B	118.4	C21H—C22H—H22H	119.7
C24B—N23B—C22B	118.0 (6)	C22H—N23H—C24H	123 (2)
N23B—C24B—C25B	123.8 (6)	C25H—C24H—N23H	119 (2)
N23B—C24B—H24B	118.1	C25H—C24H—H24H	120.4
C25B—C24B—H24B	118.1	N23H—C24H—H24H	120.4
C26B—C25B—C24B	117.1 (6)	C24H—C25H—C26H	117.3 (16)
C26B—C25B—H25B	121.5	C24H—C25H—H25H	121.3
C24B—C25B—H25B	121.5	C26H—C25H—H25H	121.3
C21B—C26B—C25B	120.5 (6)	C25H—C26H—C21H	126.9 (12)
C21B—C26B—H26B	119.8	C25H—C26H—H26H	116.6
C25B—C26B—H26B	119.8	C21H—C26H—H26H	116.6
O1C—C1C—N1C	124.3 (6)	O1W—C1W—N1W	119 (3)
O1C—C1C—C11C	123.1 (6)	O1W—C1W—C21W	132 (4)
N1C—C1C—C11C	112.4 (7)	N1W—C1W—C21W	108 (3)
C1C—N1C—C21C	126.8 (6)	C1W—N1W—C11W	124 (4)
C1C—N1C—H1C	116.6	C1W—N1W—H1W	117.8
C21C—N1C—H1C	116.6	C11W—N1W—H1W	117.8
C12C—C11C—C16C	115.9 (5)	N1W—C11W—C12W	117 (4)
C12C—C11C—C1C	127.7 (6)	N1W—C11W—C16W	123 (4)
C16C—C11C—C1C	116.1 (7)	C12W—C11W—C16W	120.0
C11C—C12C—F12C	119.4 (6)	N13W—C12W—C11W	120.0
C11C—C12C—C13C	126.8 (7)	N13W—C12W—H12W	120.0
F12C—C12C—C13C	113.4 (8)	C11W—C12W—H12W	120.0
C14C—C13C—C12C	115.1 (9)	C12W—N13W—C14W	120.0
C14C—C13C—H13C	122.5	C15W—C14W—N13W	120.0
C12C—C13C—H13C	122.5	C15W—C14W—H14W	120.0
C13C—C14C—C15C	121.1 (6)	N13W—C14W—H14W	120.0
C13C—C14C—H14C	119.5	C16W—C15W—C14W	120.0
C15C—C14C—H14C	119.5	C16W—C15W—H15W	120.0
C16C—C15C—C14C	120.5 (6)	C14W—C15W—H15W	120.0
C16C—C15C—H15C	119.7	C15W—C16W—C11W	120.0
C14C—C15C—H15C	119.7	C15W—C16W—H16W	120.0
C15C—C16C—C11C	120.5 (7)	C11W—C16W—H16W	120.0
C15C—C16C—H16C	119.7	C22W—C21W—C26W	120.0
C11C—C16C—H16C	119.7	C22W—C21W—C1W	127 (3)
C22C—C21C—C26C	119.7 (5)	C26W—C21W—C1W	113 (3)
C22C—C21C—N1C	117.8 (5)	F22W—C22W—C21W	125 (3)
C26C—C21C—N1C	122.3 (6)	F22W—C22W—C23W	114 (3)
N23C—C22C—C21C	125.0 (5)	C21W—C22W—C23W	120.0
N23C—C22C—H22C	117.5	C22W—C23W—C24W	120.0
C21C—C22C—H22C	117.5	C22W—C23W—H23W	120.0
C22C—N23C—C24C	114.9 (6)	C24W—C23W—H23W	120.0
C25C—C24C—N23C	123.0 (5)	C25W—C24W—C23W	120.0
C25C—C24C—H24C	118.5	C25W—C24W—H24W	120.0
N23C—C24C—H24C	118.5	C23W—C24W—H24W	120.0
C24C—C25C—C26C	122.6 (6)	C24W—C25W—C26W	120.0
C24C—C25C—H25C	118.7	C24W—C25W—H25W	120.0
C26C—C25C—H25C	118.7	C26W—C25W—H25W	120.0
C21C—C26C—C25C	114.7 (7)	C25W—C26W—C21W	120.0
C21C—C26C—H26C	122.7	C25W—C26W—H26W	120.0
C25C—C26C—H26C	122.7	C21W—C26W—H26W	120.0
O1D—C1D—N1D	123.5 (7)	O1X—C1X—N1X	124 (3)
O1D—C1D—C11D	119.5 (7)	O1X—C1X—C21X	107 (3)
N1D—C1D—C11D	117.0 (6)	N1X—C1X—C21X	129 (3)
C1D—N1D—C21D	125.3 (5)	C1X—N1X—C11X	130 (3)
C1D—N1D—H1D	117.3	C1X—N1X—H1X	114.9
C21D—N1D—H1D	117.3	C11X—N1X—H1X	114.9
C16D—C11D—C12D	115.1 (5)	N1X—C11X—C12X	118 (3)
C16D—C11D—C1D	121.0 (6)	N1X—C11X—C16X	122 (3)
C12D—C11D—C1D	123.8 (5)	C12X—C11X—C16X	120.0
F12D—C12D—C13D	118.6 (6)	C11X—C12X—N13X	120.0
F12D—C12D—C11D	119.6 (5)	C11X—C12X—H12X	120.0
C13D—C12D—C11D	121.8 (6)	N13X—C12X—H12X	120.0
C14D—C13D—C12D	121.6 (7)	C12X—N13X—C14X	120.0
C14D—C13D—H13D	119.2	C15X—C14X—N13X	120.0
C12D—C13D—H13D	119.2	C15X—C14X—H14X	120.0
C13D—C14D—C15D	120.2 (6)	N13X—C14X—H14X	120.0
C13D—C14D—H14D	119.9	C14X—C15X—C16X	120.0
C15D—C14D—H14D	119.9	C14X—C15X—H15X	120.0
C16D—C15D—C14D	118.4 (6)	C16X—C15X—H15X	120.0
C16D—C15D—H15D	120.8	C15X—C16X—C11X	120.0
C14D—C15D—H15D	120.8	C15X—C16X—H16X	120.0
C11D—C16D—C15D	122.8 (7)	C11X—C16X—H16X	120.0
C11D—C16D—H16D	118.6	C22X—C21X—C26X	120.0
C15D—C16D—H16D	118.6	C22X—C21X—C1X	111 (3)
C26D—C21D—N1D	127.0 (6)	C26X—C21X—C1X	128 (3)
C26D—C21D—C22D	118.3 (4)	C23X—C22X—C21X	120.0
N1D—C21D—C22D	114.7 (5)	C23X—C22X—F22X	113 (2)
N23D—C22D—C21D	123.7 (5)	C21X—C22X—F22X	127 (2)
N23D—C22D—H22D	118.1	C22X—C23X—C24X	120.0
C21D—C22D—H22D	118.1	C22X—C23X—H23X	120.0
C22D—N23D—C24D	116.6 (6)	C24X—C23X—H23X	120.0
C25D—C24D—N23D	123.8 (5)	C25X—C24X—C23X	120.0
C25D—C24D—H24D	118.1	C25X—C24X—H24X	120.0
N23D—C24D—H24D	118.1	C23X—C24X—H24X	120.0
C24D—C25D—C26D	121.2 (6)	C24X—C25X—C26X	120.0
C24D—C25D—H25D	119.4	C24X—C25X—H25X	120.0
C26D—C25D—H25D	119.4	C26X—C25X—H25X	120.0
C21D—C26D—C25D	116.3 (6)	C25X—C26X—C21X	120.0
C21D—C26D—H26D	121.8	C25X—C26X—H26X	120.0
C25D—C26D—H26D	121.8	C21X—C26X—H26X	120.0
O1E—C1E—N1E	123 (2)	O1Y—C1Y—N1Y	113 (2)
O1E—C1E—C11E	125 (2)	O1Y—C1Y—C21Y	129 (3)
N1E—C1E—C11E	111.6 (12)	N1Y—C1Y—C21Y	111.7 (19)
C1E—N1E—C21E	127.7 (10)	C1Y—N1Y—C11Y	109.4 (19)
C1E—N1E—H1E	116.2	C1Y—N1Y—H1Y	125.3
C21E—N1E—H1E	116.2	C11Y—N1Y—H1Y	125.3
C12E—C11E—C16E	112.5 (15)	C12Y—C11Y—C16Y	120.0
C12E—C11E—C1E	129.5 (14)	C12Y—C11Y—N1Y	102.8 (16)
C16E—C11E—C1E	116.7 (16)	C16Y—C11Y—N1Y	125.2 (19)
C11E—C12E—F12E	120.6 (10)	C11Y—C12Y—N13Y	120.0
C11E—C12E—C13E	126.7 (17)	C11Y—C12Y—H12Y	120.0
F12E—C12E—C13E	112.7 (16)	N13Y—C12Y—H12Y	120.0
C14E—C13E—C12E	119 (2)	C14Y—N13Y—C12Y	120.0
C14E—C13E—H13E	120.6	N13Y—C14Y—C15Y	120.0
C12E—C13E—H13E	120.6	N13Y—C14Y—H14Y	120.0
C15E—C14E—C13E	118 (2)	C15Y—C14Y—H14Y	120.0
C15E—C14E—H14E	121.2	C16Y—C15Y—C14Y	120.0
C13E—C14E—H14E	121.2	C16Y—C15Y—H15Y	120.0
C14E—C15E—C16E	119 (3)	C14Y—C15Y—H15Y	120.0
C14E—C15E—H15E	120.6	C15Y—C16Y—C11Y	120.0
C16E—C15E—H15E	120.6	C15Y—C16Y—H16Y	120.0
C11E—C16E—C15E	124 (3)	C11Y—C16Y—H16Y	120.0
C11E—C16E—H16E	117.9	C22Y—C21Y—C26Y	120.0
C15E—C16E—H16E	117.9	C22Y—C21Y—C1Y	131.1 (18)
C22E—C21E—N1E	116.7 (11)	C26Y—C21Y—C1Y	108.7 (18)
C22E—C21E—C26E	115.8 (12)	F22Y—C22Y—C23Y	123.3 (17)
N1E—C21E—C26E	127.3 (13)	F22Y—C22Y—C21Y	116.5 (16)
C21E—C22E—N23E	125.2 (12)	C23Y—C22Y—C21Y	120.0
C21E—C22E—H22E	117.4	C22Y—C23Y—C24Y	120.0
N23E—C22E—H22E	117.4	C22Y—C23Y—H23Y	120.0
C24E—N23E—C22E	117.6 (14)	C24Y—C23Y—H23Y	120.0
N23E—C24E—C25E	120 (2)	C25Y—C24Y—C23Y	120.0
N23E—C24E—H24E	120.2	C25Y—C24Y—H24Y	120.0
C25E—C24E—H24E	120.2	C23Y—C24Y—H24Y	120.0
C26E—C25E—C24E	124 (3)	C24Y—C25Y—C26Y	120.0
C26E—C25E—H25E	117.8	C24Y—C25Y—H25Y	120.0
C24E—C25E—H25E	117.8	C26Y—C25Y—H25Y	120.0
C25E—C26E—C21E	116 (2)	C25Y—C26Y—C21Y	120.0
C25E—C26E—H26E	121.9	C25Y—C26Y—H26Y	120.0
C21E—C26E—H26E	121.9	C21Y—C26Y—H26Y	120.0
O1G—C1G—N1G	126 (3)	O1Z—C1Z—N1Z	123 (3)
O1G—C1G—C11G	120 (3)	O1Z—C1Z—C21Z	110 (5)
N1G—C1G—C11G	113.6 (13)	N1Z—C1Z—C21Z	127 (5)
C1G—N1G—C21G	126.4 (13)	C1Z—N1Z—C11Z	129 (3)
C1G—N1G—H1G	116.8	C1Z—N1Z—H1Z	115.4
C21G—N1G—H1G	116.8	C11Z—N1Z—H1Z	115.4
C16G—C11G—C12G	114.7 (16)	N1Z—C11Z—C12Z	115 (3)
C16G—C11G—C1G	115.3 (18)	N1Z—C11Z—C16Z	124 (3)
C12G—C11G—C1G	129.8 (15)	C12Z—C11Z—C16Z	120.0
C11G—C12G—F12G	119.2 (11)	N13Z—C12Z—C11Z	120.0
C11G—C12G—C13G	128.9 (14)	N13Z—C12Z—H12Z	120.0
F12G—C12G—C13G	111.7 (14)	C11Z—C12Z—H12Z	120.0
C12G—C13G—C14G	110.8 (16)	C12Z—N13Z—C14Z	120.0
C12G—C13G—H13G	124.6	C15Z—C14Z—N13Z	120.0
C14G—C13G—H13G	124.6	C15Z—C14Z—H14Z	120.0
C15G—C14G—C13G	124 (2)	N13Z—C14Z—H14Z	120.0
C15G—C14G—H14G	117.8	C16Z—C15Z—C14Z	120.0
C13G—C14G—H14G	117.8	C16Z—C15Z—H15Z	120.0
C14G—C15G—C16G	114 (3)	C14Z—C15Z—H15Z	120.0
C14G—C15G—H15G	123.1	C15Z—C16Z—C11Z	120.0
C16G—C15G—H15G	123.1	C15Z—C16Z—H16Z	120.0
C11G—C16G—C15G	126 (3)	C11Z—C16Z—H16Z	120.0
C11G—C16G—H16G	116.9	C22Z—C21Z—C26Z	120.0
C15G—C16G—H16G	116.9	C22Z—C21Z—C1Z	112 (7)
C22G—C21G—N1G	116.3 (17)	C26Z—C21Z—C1Z	127 (7)
C22G—C21G—C26G	124.8 (16)	C21Z—C22Z—C23Z	120.0
N1G—C21G—C26G	118.9 (19)	C21Z—C22Z—F22Z	131 (7)
N23G—C22G—C21G	126.9 (15)	C23Z—C22Z—F22Z	108 (7)
N23G—C22G—H22G	116.5	C24Z—C23Z—C22Z	120.0
C21G—C22G—H22G	116.5	C24Z—C23Z—H23Z	120.0
C22G—N23G—C24G	108.3 (19)	C22Z—C23Z—H23Z	120.0
C25G—C24G—N23G	125 (3)	C23Z—C24Z—C25Z	120.0
C25G—C24G—H24G	117.7	C23Z—C24Z—H24Z	120.0
N23G—C24G—H24G	117.7	C25Z—C24Z—H24Z	120.0
C24G—C25G—C26G	129 (4)	C26Z—C25Z—C24Z	120.0
C24G—C25G—H25G	115.4	C26Z—C25Z—H25Z	120.0
C26G—C25G—H25G	115.4	C24Z—C25Z—H25Z	120.0
C25G—C26G—C21G	106 (3)	C25Z—C26Z—C21Z	120.0
C25G—C26G—H26G	127.1	C25Z—C26Z—H26Z	120.0
C21G—C26G—H26G	127.1	C21Z—C26Z—H26Z	120.0
O1A—C1A—N1A—C21A	7.1 (10)	O1F—C1F—N1F—C21F	−10 (4)
C11A—C1A—N1A—C21A	−173.6 (5)	C11F—C1F—N1F—C21F	179.5 (15)
O1A—C1A—C11A—C12A	−147.7 (7)	O1F—C1F—C11F—C16F	−27 (4)
N1A—C1A—C11A—C12A	33.1 (9)	N1F—C1F—C11F—C16F	144 (2)
O1A—C1A—C11A—C16A	24.7 (9)	O1F—C1F—C11F—C12F	157 (2)
N1A—C1A—C11A—C16A	−154.5 (6)	N1F—C1F—C11F—C12F	−32 (3)
C16A—C11A—C12A—C13A	5.3 (9)	C16F—C11F—C12F—F12F	−176 (2)
C1A—C11A—C12A—C13A	177.5 (6)	C1F—C11F—C12F—F12F	0 (2)
C16A—C11A—C12A—F12A	−173.5 (5)	C16F—C11F—C12F—C13F	6 (3)
C1A—C11A—C12A—F12A	−1.3 (9)	C1F—C11F—C12F—C13F	−178.3 (16)
C11A—C12A—C13A—C14A	−0.5 (9)	F12F—C12F—C13F—C14F	−179 (2)
F12A—C12A—C13A—C14A	178.4 (6)	C11F—C12F—C13F—C14F	−1 (3)
C12A—C13A—C14A—C15A	−2.9 (10)	C12F—C13F—C14F—C15F	0 (5)
C13A—C14A—C15A—C16A	1.1 (12)	C13F—C14F—C15F—C16F	−3 (5)
C14A—C15A—C16A—C11A	3.8 (10)	C12F—C11F—C16F—C15F	−10 (5)
C12A—C11A—C16A—C15A	−6.7 (8)	C1F—C11F—C16F—C15F	173 (3)
C1A—C11A—C16A—C15A	−179.9 (6)	C14F—C15F—C16F—C11F	9 (5)
C1A—N1A—C21A—C22A	155.1 (6)	C1F—N1F—C21F—C26F	−154.3 (16)
C1A—N1A—C21A—C26A	−26.4 (8)	C1F—N1F—C21F—C22F	22 (2)
N1A—C21A—C22A—N23A	179.6 (5)	N1F—C21F—C22F—N23F	−178.0 (14)
C26A—C21A—C22A—N23A	1.1 (8)	C26F—C21F—C22F—N23F	−2 (2)
C21A—C22A—N23A—C24A	−1.2 (9)	C21F—C22F—N23F—C24F	−2 (4)
C22A—N23A—C24A—C25A	1.0 (9)	C22F—N23F—C24F—C25F	3 (5)
N23A—C24A—C25A—C26A	−0.8 (10)	N23F—C24F—C25F—C26F	0 (3)
C24A—C25A—C26A—C21A	0.6 (9)	C24F—C25F—C26F—C21F	−4 (3)
C22A—C21A—C26A—C25A	−0.7 (8)	N1F—C21F—C26F—C25F	−178.9 (13)
N1A—C21A—C26A—C25A	−179.2 (5)	C22F—C21F—C26F—C25F	5 (2)
O1B—C1B—N1B—C21B	8.3 (11)	O1H—C1H—N1H—C21H	1 (4)
C11B—C1B—N1B—C21B	−174.9 (5)	C11H—C1H—N1H—C21H	−171.7 (15)
O1B—C1B—C11B—C16B	22.6 (11)	O1H—C1H—C11H—C16H	39 (5)
N1B—C1B—C11B—C16B	−154.3 (6)	N1H—C1H—C11H—C16H	−148 (3)
O1B—C1B—C11B—C12B	−151.7 (8)	O1H—C1H—C11H—C12H	−146 (3)
N1B—C1B—C11B—C12B	31.4 (9)	N1H—C1H—C11H—C12H	26 (3)
C16B—C11B—C12B—F12B	−177.0 (5)	C16H—C11H—C12H—C13H	−6 (2)
C1B—C11B—C12B—F12B	−2.5 (8)	C1H—C11H—C12H—C13H	178.3 (18)
C16B—C11B—C12B—C13B	3.4 (8)	C16H—C11H—C12H—F12H	177.7 (19)
C1B—C11B—C12B—C13B	177.9 (6)	C1H—C11H—C12H—F12H	2 (2)
F12B—C12B—C13B—C14B	178.1 (6)	F12H—C12H—C13H—C14H	174.2 (17)
C11B—C12B—C13B—C14B	−2.3 (9)	C11H—C12H—C13H—C14H	−2 (2)
C12B—C13B—C14B—C15B	−1.3 (10)	C12H—C13H—C14H—C15H	3 (3)
C13B—C14B—C15B—C16B	3.7 (10)	C13H—C14H—C15H—C16H	3 (3)
C12B—C11B—C16B—C15B	−1.0 (8)	C12H—C11H—C16H—C15H	24 (7)
C1B—C11B—C16B—C15B	−175.7 (6)	C1H—C11H—C16H—C15H	−160 (5)
C14B—C15B—C16B—C11B	−2.4 (10)	C14H—C15H—C16H—C11H	−23 (7)
C1B—N1B—C21B—C26B	−29.4 (9)	C1H—N1H—C21H—C26H	158 (2)
C1B—N1B—C21B—C22B	155.7 (6)	C1H—N1H—C21H—C22H	−25 (3)
C26B—C21B—C22B—N23B	5.1 (9)	C26H—C21H—C22H—N23H	−4 (5)
N1B—C21B—C22B—N23B	−179.5 (5)	N1H—C21H—C22H—N23H	180 (3)
C21B—C22B—N23B—C24B	−3.0 (9)	C21H—C22H—N23H—C24H	4 (5)
C22B—N23B—C24B—C25B	1.2 (10)	C22H—N23H—C24H—C25H	0 (5)
N23B—C24B—C25B—C26B	−1.7 (10)	N23H—C24H—C25H—C26H	−3 (3)
C22B—C21B—C26B—C25B	−5.4 (9)	C24H—C25H—C26H—C21H	3 (3)
N1B—C21B—C26B—C25B	179.8 (6)	N1H—C21H—C26H—C25H	176.9 (13)
C24B—C25B—C26B—C21B	3.8 (10)	C22H—C21H—C26H—C25H	0 (3)
O1C—C1C—N1C—C21C	−10.8 (10)	O1W—C1W—N1W—C11W	−20 (10)
C11C—C1C—N1C—C21C	174.2 (5)	C21W—C1W—N1W—C11W	171 (4)
O1C—C1C—C11C—C12C	154.4 (9)	C1W—N1W—C11W—C12W	−140 (5)
N1C—C1C—C11C—C12C	−30.6 (10)	C1W—N1W—C11W—C16W	37 (7)
O1C—C1C—C11C—C16C	−19.0 (10)	N1W—C11W—C12W—N13W	177 (4)
N1C—C1C—C11C—C16C	156.0 (7)	C16W—C11W—C12W—N13W	0.0
C16C—C11C—C12C—F12C	170.7 (8)	C11W—C12W—N13W—C14W	0.0
C1C—C11C—C12C—F12C	−2.8 (12)	C12W—N13W—C14W—C15W	0.0
C16C—C11C—C12C—C13C	−1.6 (12)	N13W—C14W—C15W—C16W	0.0
C1C—C11C—C12C—C13C	−175.0 (9)	C14W—C15W—C16W—C11W	0.0
C11C—C12C—C13C—C14C	2.4 (13)	N1W—C11W—C16W—C15W	−176 (5)
F12C—C12C—C13C—C14C	−170.3 (9)	C12W—C11W—C16W—C15W	0.0
C12C—C13C—C14C—C15C	−2.7 (11)	O1W—C1W—C21W—C22W	162 (7)
C13C—C14C—C15C—C16C	2.4 (11)	N1W—C1W—C21W—C22W	−31 (7)
C14C—C15C—C16C—C11C	−1.5 (10)	O1W—C1W—C21W—C26W	−26 (10)
C12C—C11C—C16C—C15C	1.1 (10)	N1W—C1W—C21W—C26W	141 (5)
C1C—C11C—C16C—C15C	175.3 (8)	C26W—C21W—C22W—F22W	−176 (4)
C1C—N1C—C21C—C22C	−151.6 (6)	C1W—C21W—C22W—F22W	−3 (5)
C1C—N1C—C21C—C26C	22.8 (10)	C26W—C21W—C22W—C23W	0.0
C26C—C21C—C22C—N23C	5.3 (11)	C1W—C21W—C22W—C23W	172 (4)
N1C—C21C—C22C—N23C	179.8 (6)	F22W—C22W—C23W—C24W	176 (4)
C21C—C22C—N23C—C24C	−4.0 (11)	C21W—C22W—C23W—C24W	0.0
C22C—N23C—C24C—C25C	2.3 (14)	C22W—C23W—C24W—C25W	0.0
N23C—C24C—C25C—C26C	−2.0 (16)	C23W—C24W—C25W—C26W	0.0
C22C—C21C—C26C—C25C	−4.3 (10)	C24W—C25W—C26W—C21W	0.0
N1C—C21C—C26C—C25C	−178.6 (6)	C22W—C21W—C26W—C25W	0.0
C24C—C25C—C26C—C21C	2.9 (12)	C1W—C21W—C26W—C25W	−173 (4)
O1D—C1D—N1D—C21D	−6.6 (10)	O1X—C1X—N1X—C11X	−4 (11)
C11D—C1D—N1D—C21D	175.1 (5)	C21X—C1X—N1X—C11X	177 (4)
O1D—C1D—C11D—C16D	−34.1 (10)	C1X—N1X—C11X—C12X	−151 (5)
N1D—C1D—C11D—C16D	144.3 (6)	C1X—N1X—C11X—C16X	28 (6)
O1D—C1D—C11D—C12D	150.3 (7)	N1X—C11X—C12X—N13X	179 (3)
N1D—C1D—C11D—C12D	−31.3 (8)	C16X—C11X—C12X—N13X	0.0
C16D—C11D—C12D—F12D	−177.9 (6)	C11X—C12X—N13X—C14X	0.0
C1D—C11D—C12D—F12D	−2.0 (8)	C12X—N13X—C14X—C15X	0.0
C16D—C11D—C12D—C13D	3.4 (8)	N13X—C14X—C15X—C16X	0.0
C1D—C11D—C12D—C13D	179.2 (6)	C14X—C15X—C16X—C11X	0.0
F12D—C12D—C13D—C14D	−179.3 (6)	N1X—C11X—C16X—C15X	−179 (3)
C11D—C12D—C13D—C14D	−0.6 (9)	C12X—C11X—C16X—C15X	0.0
C12D—C13D—C14D—C15D	−1.4 (10)	O1X—C1X—C21X—C22X	153 (5)
C13D—C14D—C15D—C16D	0.5 (11)	N1X—C1X—C21X—C22X	−27 (8)
C12D—C11D—C16D—C15D	−4.3 (10)	O1X—C1X—C21X—C26X	−34 (8)
C1D—C11D—C16D—C15D	179.7 (7)	N1X—C1X—C21X—C26X	146 (5)
C14D—C15D—C16D—C11D	2.5 (11)	C26X—C21X—C22X—C23X	0.0
C1D—N1D—C21D—C26D	27.8 (8)	C1X—C21X—C22X—C23X	174 (4)
C1D—N1D—C21D—C22D	−154.0 (5)	C26X—C21X—C22X—F22X	−176 (4)
C26D—C21D—C22D—N23D	−0.8 (8)	C1X—C21X—C22X—F22X	−2 (4)
N1D—C21D—C22D—N23D	−179.2 (5)	C21X—C22X—C23X—C24X	0.0
C21D—C22D—N23D—C24D	−1.3 (8)	F22X—C22X—C23X—C24X	176 (3)
C22D—N23D—C24D—C25D	2.8 (9)	C22X—C23X—C24X—C25X	0.0
N23D—C24D—C25D—C26D	−2.3 (10)	C23X—C24X—C25X—C26X	0.0
N1D—C21D—C26D—C25D	179.5 (5)	C24X—C25X—C26X—C21X	0.0
C22D—C21D—C26D—C25D	1.4 (8)	C22X—C21X—C26X—C25X	0.0
C24D—C25D—C26D—C21D	0.1 (8)	C1X—C21X—C26X—C25X	−173 (5)
O1E—C1E—N1E—C21E	11 (4)	O1Y—C1Y—N1Y—C11Y	3 (4)
C11E—C1E—N1E—C21E	−173.7 (13)	C21Y—C1Y—N1Y—C11Y	−153 (2)
O1E—C1E—C11E—C12E	−150 (3)	C1Y—N1Y—C11Y—C12Y	148 (2)
N1E—C1E—C11E—C12E	35 (2)	C1Y—N1Y—C11Y—C16Y	−70 (3)
O1E—C1E—C11E—C16E	16 (4)	C16Y—C11Y—C12Y—N13Y	0.0
N1E—C1E—C11E—C16E	−159.1 (14)	N1Y—C11Y—C12Y—N13Y	144 (2)
C16E—C11E—C12E—F12E	−168.6 (13)	C11Y—C12Y—N13Y—C14Y	0.0
C1E—C11E—C12E—F12E	−2 (2)	C12Y—N13Y—C14Y—C15Y	0.0
C16E—C11E—C12E—C13E	11 (2)	N13Y—C14Y—C15Y—C16Y	0.0
C1E—C11E—C12E—C13E	177.3 (19)	C14Y—C15Y—C16Y—C11Y	0.0
C11E—C12E—C13E—C14E	−2 (3)	C12Y—C11Y—C16Y—C15Y	0.0
F12E—C12E—C13E—C14E	178 (2)	N1Y—C11Y—C16Y—C15Y	−136 (3)
C12E—C13E—C14E—C15E	−6 (4)	O1Y—C1Y—C21Y—C22Y	−106 (3)
C13E—C14E—C15E—C16E	4 (5)	N1Y—C1Y—C21Y—C22Y	45 (4)
C12E—C11E—C16E—C15E	−13 (3)	O1Y—C1Y—C21Y—C26Y	68 (4)
C1E—C11E—C16E—C15E	179 (2)	N1Y—C1Y—C21Y—C26Y	−141 (2)
C14E—C15E—C16E—C11E	6 (4)	C26Y—C21Y—C22Y—F22Y	176 (2)
C1E—N1E—C21E—C22E	153.9 (14)	C1Y—C21Y—C22Y—F22Y	−11 (3)
C1E—N1E—C21E—C26E	−22 (2)	C26Y—C21Y—C22Y—C23Y	0.0
N1E—C21E—C22E—N23E	178.7 (12)	C1Y—C21Y—C22Y—C23Y	174 (3)
C26E—C21E—C22E—N23E	−5 (2)	F22Y—C22Y—C23Y—C24Y	−175 (3)
C21E—C22E—N23E—C24E	3 (2)	C21Y—C22Y—C23Y—C24Y	0.0
C22E—N23E—C24E—C25E	−5 (3)	C22Y—C23Y—C24Y—C25Y	0.0
N23E—C24E—C25E—C26E	11 (4)	C23Y—C24Y—C25Y—C26Y	0.0
C24E—C25E—C26E—C21E	−12 (4)	C24Y—C25Y—C26Y—C21Y	0.0
C22E—C21E—C26E—C25E	9 (3)	C22Y—C21Y—C26Y—C25Y	0.0
N1E—C21E—C26E—C25E	−175 (2)	C1Y—C21Y—C26Y—C25Y	−175 (2)
O1G—C1G—N1G—C21G	1 (4)	O1Z—C1Z—N1Z—C11Z	5 (8)
C11G—C1G—N1G—C21G	174.0 (15)	C21Z—C1Z—N1Z—C11Z	−168 (5)
O1G—C1G—C11G—C16G	−38 (4)	C1Z—N1Z—C11Z—C12Z	175 (4)
N1G—C1G—C11G—C16G	149 (2)	C1Z—N1Z—C11Z—C16Z	−13 (6)
O1G—C1G—C11G—C12G	148 (3)	N1Z—C11Z—C12Z—N13Z	172 (3)
N1G—C1G—C11G—C12G	−25 (2)	C16Z—C11Z—C12Z—N13Z	0.0
C16G—C11G—C12G—F12G	−179.6 (18)	C11Z—C12Z—N13Z—C14Z	0.0
C1G—C11G—C12G—F12G	−5 (2)	C12Z—N13Z—C14Z—C15Z	0.0
C16G—C11G—C12G—C13G	5 (3)	N13Z—C14Z—C15Z—C16Z	0.0
C1G—C11G—C12G—C13G	180.0 (15)	C14Z—C15Z—C16Z—C11Z	0.0
C11G—C12G—C13G—C14G	−3 (2)	N1Z—C11Z—C16Z—C15Z	−172 (4)
F12G—C12G—C13G—C14G	−177.9 (14)	C12Z—C11Z—C16Z—C15Z	0.0
C12G—C13G—C14G—C15G	5 (3)	O1Z—C1Z—C21Z—C22Z	−144 (5)
C13G—C14G—C15G—C16G	−9 (4)	N1Z—C1Z—C21Z—C22Z	29 (8)
C12G—C11G—C16G—C15G	−10 (4)	O1Z—C1Z—C21Z—C26Z	26 (8)
C1G—C11G—C16G—C15G	175 (2)	N1Z—C1Z—C21Z—C26Z	−161 (5)
C14G—C15G—C16G—C11G	12 (4)	C26Z—C21Z—C22Z—C23Z	0.0
C1G—N1G—C21G—C22G	−148.5 (15)	C1Z—C21Z—C22Z—C23Z	171 (7)
C1G—N1G—C21G—C26G	30 (2)	C26Z—C21Z—C22Z—F22Z	169 (7)
N1G—C21G—C22G—N23G	−177.8 (17)	C1Z—C21Z—C22Z—F22Z	−20 (7)
C26G—C21G—C22G—N23G	4 (3)	C21Z—C22Z—C23Z—C24Z	0.0
C21G—C22G—N23G—C24G	−5 (3)	F22Z—C22Z—C23Z—C24Z	−171 (6)
C22G—N23G—C24G—C25G	6 (4)	C22Z—C23Z—C24Z—C25Z	0.0
N23G—C24G—C25G—C26G	−5 (6)	C23Z—C24Z—C25Z—C26Z	0.0
C24G—C25G—C26G—C21G	3 (5)	C24Z—C25Z—C26Z—C21Z	0.0
C22G—C21G—C26G—C25G	−2 (3)	C22Z—C21Z—C26Z—C25Z	0.0
N1G—C21G—C26G—C25G	−180 (2)	C1Z—C21Z—C26Z—C25Z	−169 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1A^i	0.86	2.32	3.117 (8)	154
N1B—H1B···O1B^ii	0.86	2.31	3.099 (10)	153
N1C—H1C···O1C^i	0.86	2.29	3.074 (8)	152
N1D—H1D···O1D^ii	0.86	2.29	3.093 (9)	157
N1E—H1E···O1E^i	0.86	2.35	3.15 (3)	155
N1G—H1G···O1G^i	0.86	2.25	3.05 (3)	155
N1F—H1F···O1F^ii	0.86	2.36	3.15 (2)	153
N1H—H1H···O1H^ii	0.86	2.29	3.08 (3)	153
N1A—H1A···F12A	0.86	2.26	2.766 (5)	118
N1B—H1B···F12B	0.86	2.19	2.720 (5)	119
N1C—H1C···F12C	0.86	2.20	2.727 (5)	119
N1D—H1D···F12D	0.86	2.22	2.723 (5)	117
N1E—H1E···F12E	0.86	2.26	2.773 (9)	118
N1F—H1F···F12F	0.86	2.16	2.698 (9)	120
N1G—H1G···F12G	0.86	2.18	2.727 (11)	122
N1H—H1H···F12H	0.86	2.19	2.720 (10)	120

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

(Fom_F-11-061) 2-Fluoro-N-(pyridin-3-yl)benzamide

Crystal data

C12H9FN2O	F(000) = 448
Mr = 216.21	Dx = 1.455 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1933 reflections
a = 5.4788 (2) Å	θ = 2.6–27.5°
b = 8.8223 (4) Å	µ = 0.11 mm^−1
c = 20.4414 (7) Å	T = 294 K
β = 92.150 (4)°	Block, colourless
V = 987.35 (7) Å^3	0.49 × 0.25 × 0.12 mm
Z = 4

Data collection

Xcalibur, Sapphire3, Gemini Ultra diffractometer	1599 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.027
Graphite monochromator	θmax = 27.8°, θmin = 2.5°
ω scans	h = −7→6
Absorption correction: analytical (ABSFAC, Clark and Reid, 1998)	k = −11→11
Tmin = 0.949, Tmax = 0.987	l = −25→25
7439 measured reflections	7692 standard reflections every 60 min
2178 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0574P)^2 + 0.0509P] where P = (Fo^2 + 2Fc^2)/3
2178 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F12	0.30000 (17)	0.14212 (11)	0.03176 (4)	0.0653 (3)
O1	−0.32635 (19)	0.19644 (13)	−0.08572 (5)	0.0603 (3)
C1	−0.1209 (3)	0.19535 (16)	−0.06046 (7)	0.0463 (4)
N1	0.0737 (3)	0.13310 (14)	−0.08955 (7)	0.0503 (4)
H1	0.208 (3)	0.1374 (18)	−0.0676 (8)	0.058 (5)*
C11	−0.0713 (3)	0.26922 (15)	0.00498 (7)	0.0427 (3)
C12	0.1275 (3)	0.24621 (17)	0.04718 (7)	0.0472 (4)
C13	0.1620 (3)	0.32263 (19)	0.10533 (8)	0.0548 (4)
H13	0.2996	0.3042	0.1322	0.066*
C14	−0.0096 (3)	0.4266 (2)	0.12322 (8)	0.0570 (4)
H14	0.0122	0.4805	0.1621	0.068*
C15	−0.2136 (3)	0.45069 (18)	0.08343 (8)	0.0575 (4)
H15	−0.3320	0.5195	0.0958	0.069*
C16	−0.2427 (3)	0.37304 (17)	0.02537 (8)	0.0518 (4)
H16	−0.3817	0.3906	−0.0011	0.062*
C21	0.0725 (3)	0.04988 (16)	−0.14850 (7)	0.0448 (4)
C22	−0.1128 (3)	0.0553 (2)	−0.19618 (8)	0.0642 (5)
H22	−0.2443	0.1196	−0.1900	0.077*
N23	−0.1115 (3)	−0.0280 (2)	−0.25101 (7)	0.0728 (5)
C24	0.0789 (3)	−0.1161 (2)	−0.25990 (8)	0.0607 (5)
H24	0.0812	−0.1743	−0.2978	0.073*
C25	0.2730 (3)	−0.1262 (2)	−0.21610 (9)	0.0619 (5)
H25	0.4052	−0.1885	−0.2244	0.074*
C26	0.2687 (3)	−0.04226 (18)	−0.15959 (8)	0.0562 (4)
H26	0.3981	−0.0478	−0.1289	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F12	0.0575 (6)	0.0760 (7)	0.0613 (6)	0.0182 (5)	−0.0111 (5)	−0.0005 (5)
O1	0.0467 (7)	0.0713 (8)	0.0617 (7)	0.0041 (5)	−0.0136 (5)	−0.0125 (6)
C1	0.0480 (9)	0.0390 (8)	0.0512 (9)	−0.0016 (6)	−0.0065 (7)	0.0014 (6)
N1	0.0441 (8)	0.0541 (8)	0.0519 (8)	0.0023 (6)	−0.0090 (6)	−0.0082 (6)
C11	0.0441 (8)	0.0380 (7)	0.0456 (8)	−0.0045 (6)	−0.0050 (6)	0.0037 (6)
C12	0.0436 (8)	0.0482 (8)	0.0498 (9)	0.0002 (6)	−0.0001 (7)	0.0073 (7)
C13	0.0522 (9)	0.0662 (10)	0.0452 (9)	−0.0059 (8)	−0.0091 (7)	0.0057 (8)
C14	0.0628 (11)	0.0610 (10)	0.0469 (9)	−0.0079 (8)	−0.0016 (8)	−0.0062 (7)
C15	0.0586 (10)	0.0544 (10)	0.0590 (10)	0.0028 (8)	−0.0020 (8)	−0.0076 (8)
C16	0.0484 (9)	0.0502 (9)	0.0561 (10)	0.0010 (7)	−0.0097 (7)	−0.0016 (7)
C21	0.0470 (8)	0.0441 (8)	0.0431 (8)	−0.0042 (6)	−0.0028 (6)	0.0018 (6)
C22	0.0587 (10)	0.0826 (13)	0.0507 (10)	0.0164 (9)	−0.0084 (8)	−0.0032 (9)
N23	0.0631 (10)	0.1060 (13)	0.0482 (8)	0.0059 (9)	−0.0103 (7)	−0.0074 (8)
C24	0.0638 (11)	0.0699 (11)	0.0488 (10)	−0.0117 (9)	0.0060 (8)	−0.0079 (8)
C25	0.0597 (11)	0.0662 (11)	0.0597 (11)	0.0073 (8)	0.0006 (9)	−0.0098 (8)
C26	0.0503 (10)	0.0621 (10)	0.0553 (10)	0.0054 (8)	−0.0105 (8)	−0.0054 (8)

Geometric parameters (Å, º)

F12—C12	1.3634 (17)	C15—C16	1.375 (2)
O1—C1	1.2207 (17)	C15—H15	0.9300
C1—N1	1.356 (2)	C16—H16	0.9300
C1—C11	1.5035 (19)	C21—C26	1.373 (2)
N1—C21	1.4109 (19)	C21—C22	1.382 (2)
N1—H1	0.850 (17)	C22—N23	1.340 (2)
C11—C12	1.3787 (19)	C22—H22	0.9300
C11—C16	1.387 (2)	N23—C24	1.319 (2)
C12—C13	1.373 (2)	C24—C25	1.367 (2)
C13—C14	1.373 (2)	C24—H24	0.9300
C13—H13	0.9300	C25—C26	1.373 (2)
C14—C15	1.374 (2)	C25—H25	0.9300
C14—H14	0.9300	C26—H26	0.9300
O1—C1—N1	123.05 (14)	C16—C15—H15	120.0
O1—C1—C11	120.40 (14)	C15—C16—C11	122.05 (15)
N1—C1—C11	116.53 (13)	C15—C16—H16	119.0
C1—N1—C21	127.35 (14)	C11—C16—H16	119.0
C1—N1—H1	115.6 (12)	C26—C21—C22	117.57 (14)
C21—N1—H1	116.7 (12)	C26—C21—N1	118.07 (13)
C12—C11—C16	115.91 (14)	C22—C21—N1	124.36 (14)
C12—C11—C1	127.23 (14)	N23—C22—C21	122.98 (16)
C16—C11—C1	116.85 (13)	N23—C22—H22	118.5
F12—C12—C13	117.17 (13)	C21—C22—H22	118.5
F12—C12—C11	119.51 (13)	C24—N23—C22	117.86 (15)
C13—C12—C11	123.31 (15)	N23—C24—C25	123.21 (16)
C14—C13—C12	119.01 (15)	N23—C24—H24	118.4
C14—C13—H13	120.5	C25—C24—H24	118.4
C12—C13—H13	120.5	C24—C25—C26	118.57 (16)
C13—C14—C15	119.72 (15)	C24—C25—H25	120.7
C13—C14—H14	120.1	C26—C25—H25	120.7
C15—C14—H14	120.1	C21—C26—C25	119.78 (15)
C14—C15—C16	119.96 (16)	C21—C26—H26	120.1
C14—C15—H15	120.0	C25—C26—H26	120.1
O1—C1—N1—C21	−6.1 (2)	C14—C15—C16—C11	0.1 (3)
C11—C1—N1—C21	175.78 (12)	C12—C11—C16—C15	1.4 (2)
O1—C1—C11—C12	162.20 (15)	C1—C11—C16—C15	−178.19 (13)
N1—C1—C11—C12	−19.6 (2)	C1—N1—C21—C26	−160.11 (15)
O1—C1—C11—C16	−18.3 (2)	C1—N1—C21—C22	20.2 (2)
N1—C1—C11—C16	159.90 (13)	C26—C21—C22—N23	2.0 (3)
C16—C11—C12—F12	177.76 (13)	N1—C21—C22—N23	−178.34 (16)
C1—C11—C12—F12	−2.7 (2)	C21—C22—N23—C24	−1.5 (3)
C16—C11—C12—C13	−1.7 (2)	C22—N23—C24—C25	0.0 (3)
C1—C11—C12—C13	177.81 (14)	N23—C24—C25—C26	1.0 (3)
F12—C12—C13—C14	−178.93 (14)	C22—C21—C26—C25	−0.9 (2)
C11—C12—C13—C14	0.5 (2)	N1—C21—C26—C25	179.36 (14)
C12—C13—C14—C15	1.0 (2)	C24—C25—C26—C21	−0.5 (3)
C13—C14—C15—C16	−1.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···F12	0.850 (17)	2.074 (17)	2.7315 (16)	133.7 (15)
C16—H16···O1	0.93	2.46	2.7777 (19)	100
C22—H22···O1	0.93	2.30	2.867 (2)	119

(Fpo-10-123) 4-Fluoro-N-(pyridin-2-yl)benzamide

Crystal data

C12H9FN2O	Dx = 1.367 Mg m^−3
Mr = 216.21	Melting point: 393 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 5919 reflections
a = 24.3381 (4) Å	θ = 2.6–27.5°
b = 7.9334 (1) Å	µ = 0.10 mm^−1
c = 10.8791 (2) Å	T = 294 K
V = 2100.58 (6) Å^3	Block, colourless
Z = 8	0.58 × 0.53 × 0.17 mm
F(000) = 896

Data collection

Xcalibur, Sapphire3, Gemini Ultra diffractometer	1829 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.024
Graphite monochromator	θmax = 27.1°, θmin = 2.7°
ω scans	h = −31→31
Absorption correction: analytical (ABSFAC, Clark and Reid, 1998)	k = −10→9
Tmin = 0.943, Tmax = 0.983	l = −13→13
14121 measured reflections	15398 standard reflections every 60 min
2254 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0441P)^2 + 0.4556P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2254 reflections	Δρmax = 0.14 e Å^−3
150 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0049 (9)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F14	0.27947 (5)	0.58098 (19)	0.21424 (13)	0.1205 (5)
O1	0.08690 (5)	0.6898 (2)	0.58413 (10)	0.0894 (4)
C1	0.08502 (6)	0.6907 (2)	0.47221 (13)	0.0601 (4)
N1	0.03851 (5)	0.72299 (17)	0.40676 (11)	0.0573 (3)
H1	0.0422 (6)	0.736 (2)	0.3266 (16)	0.063 (4)*
C11	0.13551 (6)	0.65978 (19)	0.39852 (13)	0.0557 (4)
C12	0.18466 (6)	0.7247 (2)	0.44292 (16)	0.0666 (4)
H12	0.1848	0.7856	0.5160	0.080*
C13	0.23289 (7)	0.7003 (2)	0.38051 (19)	0.0777 (5)
H13	0.2657	0.7459	0.4093	0.093*
C14	0.23163 (7)	0.6080 (3)	0.27551 (18)	0.0787 (5)
C15	0.18440 (8)	0.5402 (3)	0.22916 (17)	0.0799 (5)
H15	0.1850	0.4771	0.1571	0.096*
C16	0.13576 (6)	0.5673 (2)	0.29161 (14)	0.0654 (4)
H16	0.1031	0.5229	0.2613	0.078*
C21	−0.01308 (6)	0.76908 (18)	0.45356 (13)	0.0547 (4)
N22	−0.04904 (5)	0.80967 (17)	0.36639 (11)	0.0615 (3)
C23	−0.09843 (6)	0.8627 (2)	0.40284 (17)	0.0705 (4)
H23	−0.1237	0.8938	0.3429	0.085*
C24	−0.11413 (7)	0.8739 (2)	0.52355 (17)	0.0748 (5)
H24	−0.1489	0.9127	0.5451	0.090*
C25	−0.07721 (8)	0.8265 (3)	0.61095 (17)	0.0841 (6)
H25	−0.0869	0.8299	0.6936	0.101*
C26	−0.02586 (7)	0.7736 (3)	0.57699 (15)	0.0761 (5)
H26	−0.0002	0.7416	0.6358	0.091*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F14	0.0807 (7)	0.1531 (13)	0.1277 (10)	0.0294 (7)	0.0413 (7)	0.0364 (9)
O1	0.0833 (8)	0.1400 (12)	0.0451 (6)	0.0210 (8)	−0.0079 (5)	0.0041 (7)
C1	0.0608 (9)	0.0726 (9)	0.0470 (8)	0.0018 (7)	−0.0076 (6)	0.0009 (7)
N1	0.0513 (7)	0.0803 (9)	0.0404 (6)	−0.0009 (6)	−0.0009 (5)	−0.0009 (6)
C11	0.0542 (8)	0.0633 (8)	0.0497 (7)	0.0029 (6)	−0.0072 (6)	0.0042 (6)
C12	0.0639 (9)	0.0702 (10)	0.0657 (9)	0.0011 (7)	−0.0161 (7)	0.0016 (8)
C13	0.0550 (9)	0.0816 (12)	0.0964 (14)	−0.0017 (8)	−0.0083 (9)	0.0185 (11)
C14	0.0613 (10)	0.0916 (13)	0.0833 (12)	0.0169 (9)	0.0153 (9)	0.0275 (11)
C15	0.0821 (12)	0.0936 (13)	0.0638 (10)	0.0221 (10)	0.0027 (8)	−0.0036 (9)
C16	0.0611 (9)	0.0755 (10)	0.0595 (9)	0.0048 (7)	−0.0082 (7)	−0.0056 (8)
C21	0.0534 (8)	0.0630 (8)	0.0476 (7)	−0.0059 (6)	0.0025 (6)	−0.0017 (6)
N22	0.0497 (6)	0.0796 (9)	0.0553 (7)	−0.0005 (6)	0.0025 (5)	−0.0022 (6)
C23	0.0544 (8)	0.0799 (11)	0.0771 (11)	0.0010 (8)	0.0050 (8)	−0.0010 (9)
C24	0.0634 (10)	0.0745 (10)	0.0867 (12)	−0.0003 (8)	0.0250 (9)	−0.0062 (9)
C25	0.0873 (13)	0.1020 (14)	0.0631 (10)	0.0013 (11)	0.0243 (10)	−0.0030 (10)
C26	0.0742 (11)	0.1038 (14)	0.0504 (9)	0.0053 (9)	0.0081 (8)	0.0013 (9)

Geometric parameters (Å, º)

F14—C14	1.3585 (19)	C15—C16	1.382 (2)
O1—C1	1.2185 (18)	C15—H15	0.9300
C1—N1	1.3616 (18)	C16—H16	0.9300
C1—C11	1.488 (2)	C21—N22	1.3299 (18)
N1—C21	1.4034 (18)	C21—C26	1.379 (2)
N1—H1	0.883 (17)	N22—C23	1.3339 (19)
C11—C16	1.375 (2)	C23—C24	1.371 (2)
C11—C12	1.389 (2)	C23—H23	0.9300
C12—C13	1.370 (2)	C24—C25	1.361 (3)
C12—H12	0.9300	C24—H24	0.9300
C13—C14	1.358 (3)	C25—C26	1.369 (2)
C13—H13	0.9300	C25—H25	0.9300
C14—C15	1.366 (3)	C26—H26	0.9300
O1—C1—N1	123.71 (14)	C16—C15—H15	120.7
O1—C1—C11	120.43 (13)	C11—C16—C15	120.18 (15)
N1—C1—C11	115.84 (12)	C11—C16—H16	119.9
C1—N1—C21	127.09 (12)	C15—C16—H16	119.9
C1—N1—H1	116.9 (10)	N22—C21—C26	122.66 (14)
C21—N1—H1	114.8 (10)	N22—C21—N1	113.15 (12)
C16—C11—C12	119.22 (14)	C26—C21—N1	124.19 (14)
C16—C11—C1	123.20 (13)	C21—N22—C23	117.21 (13)
C12—C11—C1	117.56 (14)	N22—C23—C24	123.82 (17)
C13—C12—C11	120.88 (16)	N22—C23—H23	118.1
C13—C12—H12	119.6	C24—C23—H23	118.1
C11—C12—H12	119.6	C25—C24—C23	117.86 (16)
C14—C13—C12	118.29 (16)	C25—C24—H24	121.1
C14—C13—H13	120.9	C23—C24—H24	121.1
C12—C13—H13	120.9	C24—C25—C26	119.91 (16)
C13—C14—F14	118.60 (18)	C24—C25—H25	120.0
C13—C14—C15	122.84 (16)	C26—C25—H25	120.0
F14—C14—C15	118.56 (19)	C25—C26—C21	118.47 (17)
C14—C15—C16	118.57 (17)	C25—C26—H26	120.8
C14—C15—H15	120.7	C21—C26—H26	120.8
O1—C1—N1—C21	3.9 (3)	C12—C11—C16—C15	−0.2 (2)
C11—C1—N1—C21	−174.57 (14)	C1—C11—C16—C15	−178.51 (15)
O1—C1—C11—C16	141.45 (17)	C14—C15—C16—C11	−0.5 (3)
N1—C1—C11—C16	−40.0 (2)	C1—N1—C21—N22	173.24 (15)
O1—C1—C11—C12	−36.8 (2)	C1—N1—C21—C26	−6.4 (3)
N1—C1—C11—C12	141.73 (15)	C26—C21—N22—C23	2.6 (2)
C16—C11—C12—C13	1.2 (2)	N1—C21—N22—C23	−176.97 (14)
C1—C11—C12—C13	179.56 (15)	C21—N22—C23—C24	−1.4 (3)
C11—C12—C13—C14	−1.4 (3)	N22—C23—C24—C25	−0.7 (3)
C12—C13—C14—F14	−178.94 (15)	C23—C24—C25—C26	1.6 (3)
C12—C13—C14—C15	0.7 (3)	C24—C25—C26—C21	−0.4 (3)
C13—C14—C15—C16	0.2 (3)	N22—C21—C26—C25	−1.8 (3)
F14—C14—C15—C16	179.87 (15)	N1—C21—C26—C25	177.77 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N22^i	0.883 (17)	2.186 (17)	3.0608 (18)	171.0 (15)
C16—H16···O1^ii	0.93	2.59	3.266 (2)	130

Symmetry codes: (i) −x, y, −z+1/2; (ii) x, −y+1, z−1/2.

(Fmo-11-003) 3-Fluoro-N-(pyridin-2-yl)benzamide

Crystal data

C12H9FN2O	Z = 4
Mr = 216.21	F(000) = 448
Triclinic, P1	Dx = 1.388 Mg m^−3
Hall symbol: -P 1	Melting point: 350 K
a = 10.4219 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7183 (4) Å	Cell parameters from 8483 reflections
c = 11.0188 (3) Å	θ = 2.6–27.5°
α = 102.286 (3)°	µ = 0.10 mm^−1
β = 97.356 (3)°	T = 294 K
γ = 117.074 (4)°	Block, colourless
V = 1034.49 (8) Å^3	0.44 × 0.35 × 0.28 mm

Data collection

Xcalibur, Sapphire3, Gemini Ultra diffractometer	3732 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.016
Graphite monochromator	θmax = 27.9°, θmin = 2.2°
ω scans	h = −13→13
Absorption correction: analytical (ABSFAC, Clark and Reid, 1998)	k = −13→13
Tmin = 0.956, Tmax = 0.972	l = −14→14
14851 measured reflections	14852 standard reflections every 60 min
4555 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0528P)^2 + 0.2446P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
4555 reflections	Δρmax = 0.29 e Å^−3
298 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.061 (4)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F13A	−0.29240 (12)	0.41665 (15)	0.06770 (12)	0.0957 (4)
O1A	0.18818 (16)	0.88056 (13)	0.35345 (12)	0.0756 (4)
C1A	0.18452 (17)	0.76828 (16)	0.36305 (14)	0.0508 (3)
N1A	0.26196 (14)	0.76022 (14)	0.46787 (11)	0.0476 (3)
H1A	0.2350 (19)	0.671 (2)	0.4701 (16)	0.059 (5)*
C11A	0.08780 (17)	0.62419 (16)	0.25985 (13)	0.0486 (3)
C12A	−0.05841 (17)	0.58739 (18)	0.20854 (14)	0.0560 (4)
H12A	−0.0933	0.6515	0.2362	0.067*
C13A	−0.14950 (18)	0.4543 (2)	0.11631 (16)	0.0628 (4)
C14A	−0.1022 (2)	0.3583 (2)	0.06974 (16)	0.0659 (4)
H14A	−0.1668	0.2690	0.0065	0.079*
C15A	0.0431 (2)	0.39720 (19)	0.11872 (16)	0.0632 (4)
H15A	0.0779	0.3342	0.0871	0.076*
C16A	0.13876 (18)	0.52877 (17)	0.21450 (15)	0.0548 (4)
H16A	0.2365	0.5530	0.2482	0.066*
C21A	0.34021 (15)	0.87123 (15)	0.58582 (13)	0.0451 (3)
N22A	0.36302 (15)	0.82075 (13)	0.68224 (12)	0.0543 (3)
C23A	0.4290 (2)	0.91773 (19)	0.80002 (16)	0.0649 (4)
H23A	0.4443	0.8834	0.8682	0.078*
C24A	0.4753 (2)	1.06430 (19)	0.82632 (17)	0.0672 (5)
H24A	0.5185	1.1276	0.9102	0.081*
C25A	0.45616 (19)	1.11517 (18)	0.72548 (18)	0.0650 (4)
H25A	0.4892	1.2149	0.7400	0.078*
C26A	0.38830 (17)	1.01927 (16)	0.60295 (16)	0.0556 (4)
H26A	0.3749	1.0524	0.5335	0.067*
F13B	0.80834 (16)	0.83722 (17)	1.15646 (12)	0.1052 (4)
O1B	0.5053 (2)	0.43699 (16)	0.7306 (2)	0.1396 (9)
C1B	0.4988 (2)	0.54625 (19)	0.7277 (2)	0.0735 (5)
N1B	0.38993 (15)	0.54411 (15)	0.64410 (13)	0.0580 (3)
H1B	0.3884 (18)	0.6262 (19)	0.6562 (15)	0.055 (4)*
C11B	0.61208 (17)	0.69173 (18)	0.82037 (17)	0.0598 (4)
C12B	0.6586 (2)	0.6981 (2)	0.94706 (19)	0.0702 (5)
H12B	0.6187	0.6137	0.9725	0.084*
C13B	0.7639 (2)	0.8309 (2)	1.03306 (18)	0.0679 (5)
C14B	0.8266 (2)	0.9564 (2)	1.00041 (19)	0.0702 (5)
H14B	0.8974	1.0452	1.0616	0.084*
C15B	0.7834 (2)	0.9499 (2)	0.87540 (19)	0.0720 (5)
H15B	0.8268	1.0347	0.8510	0.086*
C16B	0.67616 (19)	0.8185 (2)	0.78540 (18)	0.0638 (4)
H16B	0.6470	0.8154	0.7009	0.077*
C21B	0.26446 (17)	0.42092 (16)	0.55487 (15)	0.0530 (4)
N22B	0.16877 (14)	0.45414 (13)	0.49704 (12)	0.0529 (3)
C23B	0.04207 (18)	0.34301 (17)	0.41507 (15)	0.0579 (4)
H23B	−0.0263	0.3649	0.3760	0.069*
C24B	0.0070 (2)	0.19828 (18)	0.38523 (17)	0.0649 (4)
H24B	−0.0825	0.1241	0.3275	0.078*
C25B	0.1081 (2)	0.16667 (19)	0.4432 (2)	0.0744 (5)
H25B	0.0885	0.0699	0.4239	0.089*
C26B	0.2382 (2)	0.27780 (19)	0.5299 (2)	0.0720 (5)
H26B	0.3071	0.2576	0.5709	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F13A	0.0583 (6)	0.1072 (9)	0.0977 (9)	0.0364 (6)	−0.0014 (6)	0.0105 (7)
O1A	0.1040 (10)	0.0589 (7)	0.0684 (7)	0.0473 (7)	0.0017 (7)	0.0244 (6)
C1A	0.0593 (8)	0.0526 (8)	0.0498 (8)	0.0328 (7)	0.0145 (6)	0.0215 (6)
N1A	0.0551 (7)	0.0409 (6)	0.0484 (6)	0.0258 (5)	0.0081 (5)	0.0153 (5)
C11A	0.0564 (8)	0.0548 (8)	0.0413 (7)	0.0304 (7)	0.0139 (6)	0.0205 (6)
C12A	0.0598 (9)	0.0687 (10)	0.0500 (8)	0.0389 (8)	0.0157 (7)	0.0209 (7)
C13A	0.0523 (9)	0.0734 (11)	0.0556 (9)	0.0270 (8)	0.0088 (7)	0.0194 (8)
C14A	0.0696 (11)	0.0597 (10)	0.0542 (9)	0.0247 (8)	0.0115 (8)	0.0112 (7)
C15A	0.0759 (11)	0.0619 (10)	0.0581 (9)	0.0394 (9)	0.0208 (8)	0.0161 (8)
C16A	0.0573 (9)	0.0603 (9)	0.0537 (8)	0.0335 (7)	0.0146 (7)	0.0200 (7)
C21A	0.0443 (7)	0.0432 (7)	0.0516 (7)	0.0250 (6)	0.0117 (6)	0.0149 (6)
N22A	0.0641 (8)	0.0476 (7)	0.0498 (7)	0.0301 (6)	0.0040 (6)	0.0129 (5)
C23A	0.0761 (11)	0.0638 (10)	0.0510 (8)	0.0379 (9)	0.0029 (8)	0.0112 (7)
C24A	0.0683 (10)	0.0594 (10)	0.0601 (9)	0.0330 (8)	0.0016 (8)	−0.0016 (8)
C25A	0.0610 (9)	0.0418 (8)	0.0817 (11)	0.0239 (7)	0.0103 (8)	0.0080 (8)
C26A	0.0580 (9)	0.0450 (8)	0.0661 (9)	0.0264 (7)	0.0151 (7)	0.0201 (7)
F13B	0.1166 (10)	0.1237 (11)	0.0768 (8)	0.0629 (9)	0.0063 (7)	0.0372 (7)
O1B	0.1113 (13)	0.0592 (9)	0.214 (2)	0.0500 (9)	−0.0538 (13)	0.0162 (11)
C1B	0.0654 (10)	0.0555 (9)	0.1022 (14)	0.0379 (8)	0.0028 (10)	0.0222 (9)
N1B	0.0635 (8)	0.0452 (7)	0.0678 (8)	0.0335 (6)	0.0056 (6)	0.0136 (6)
C11B	0.0503 (8)	0.0590 (9)	0.0777 (11)	0.0350 (7)	0.0091 (8)	0.0217 (8)
C12B	0.0640 (10)	0.0721 (11)	0.0917 (13)	0.0414 (9)	0.0178 (9)	0.0415 (10)
C13B	0.0626 (10)	0.0834 (12)	0.0664 (10)	0.0446 (10)	0.0107 (8)	0.0235 (9)
C14B	0.0578 (10)	0.0683 (11)	0.0796 (12)	0.0318 (9)	0.0124 (9)	0.0158 (9)
C15B	0.0609 (10)	0.0652 (11)	0.0854 (13)	0.0252 (9)	0.0184 (9)	0.0296 (9)
C16B	0.0583 (9)	0.0695 (11)	0.0674 (10)	0.0330 (8)	0.0152 (8)	0.0260 (8)
C21B	0.0595 (9)	0.0476 (8)	0.0585 (8)	0.0311 (7)	0.0181 (7)	0.0169 (7)
N22B	0.0581 (7)	0.0468 (7)	0.0535 (7)	0.0258 (6)	0.0118 (6)	0.0174 (5)
C23B	0.0574 (9)	0.0549 (9)	0.0577 (9)	0.0240 (7)	0.0163 (7)	0.0189 (7)
C24B	0.0603 (9)	0.0517 (9)	0.0684 (10)	0.0185 (8)	0.0224 (8)	0.0101 (8)
C25B	0.0814 (12)	0.0445 (9)	0.0943 (13)	0.0315 (9)	0.0293 (11)	0.0113 (9)
C26B	0.0766 (11)	0.0517 (9)	0.0914 (13)	0.0399 (9)	0.0149 (10)	0.0145 (9)

Geometric parameters (Å, º)

F13A—C13A	1.3508 (19)	F13B—C13B	1.356 (2)
O1A—C1A	1.2142 (17)	O1B—C1B	1.210 (2)
C1A—N1A	1.3638 (18)	C1B—N1B	1.355 (2)
C1A—C11A	1.495 (2)	C1B—C11B	1.485 (2)
N1A—C21A	1.3990 (18)	N1B—C21B	1.402 (2)
N1A—H1A	0.876 (18)	N1B—H1B	0.870 (17)
C11A—C16A	1.387 (2)	C11B—C16B	1.380 (2)
C11A—C12A	1.391 (2)	C11B—C12B	1.394 (2)
C12A—C13A	1.369 (2)	C12B—C13B	1.366 (3)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.366 (3)	C13B—C14B	1.354 (3)
C14A—C15A	1.370 (2)	C14B—C15B	1.370 (3)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—C16A	1.383 (2)	C15B—C16B	1.380 (3)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—H16A	0.9300	C16B—H16B	0.9300
C21A—N22A	1.3324 (18)	C21B—N22B	1.3358 (19)
C21A—C26A	1.3889 (19)	C21B—C26B	1.387 (2)
N22A—C23A	1.336 (2)	N22B—C23B	1.335 (2)
C23A—C24A	1.366 (2)	C23B—C24B	1.373 (2)
C23A—H23A	0.9300	C23B—H23B	0.9300
C24A—C25A	1.368 (3)	C24B—C25B	1.370 (3)
C24A—H24A	0.9300	C24B—H24B	0.9300
C25A—C26A	1.372 (2)	C25B—C26B	1.373 (3)
C25A—H25A	0.9300	C25B—H25B	0.9300
C26A—H26A	0.9300	C26B—H26B	0.9300
O1A—C1A—N1A	124.10 (14)	O1B—C1B—N1B	123.31 (18)
O1A—C1A—C11A	121.53 (13)	O1B—C1B—C11B	120.10 (16)
N1A—C1A—C11A	114.34 (12)	N1B—C1B—C11B	116.57 (14)
C1A—N1A—C21A	126.24 (12)	C1B—N1B—C21B	127.75 (14)
C1A—N1A—H1A	114.9 (11)	C1B—N1B—H1B	116.2 (11)
C21A—N1A—H1A	115.5 (11)	C21B—N1B—H1B	115.0 (11)
C16A—C11A—C12A	119.90 (14)	C16B—C11B—C12B	119.09 (17)
C16A—C11A—C1A	122.62 (13)	C16B—C11B—C1B	122.90 (17)
C12A—C11A—C1A	117.48 (13)	C12B—C11B—C1B	117.97 (16)
C13A—C12A—C11A	118.22 (15)	C13B—C12B—C11B	118.63 (17)
C13A—C12A—H12A	120.9	C13B—C12B—H12B	120.7
C11A—C12A—H12A	120.9	C11B—C12B—H12B	120.7
F13A—C13A—C14A	118.37 (16)	C14B—C13B—F13B	118.47 (18)
F13A—C13A—C12A	118.54 (16)	C14B—C13B—C12B	122.90 (17)
C14A—C13A—C12A	123.09 (15)	F13B—C13B—C12B	118.62 (17)
C13A—C14A—C15A	118.20 (16)	C13B—C14B—C15B	118.58 (18)
C13A—C14A—H14A	120.9	C13B—C14B—H14B	120.7
C15A—C14A—H14A	120.9	C15B—C14B—H14B	120.7
C14A—C15A—C16A	121.05 (16)	C14B—C15B—C16B	120.58 (18)
C14A—C15A—H15A	119.5	C14B—C15B—H15B	119.7
C16A—C15A—H15A	119.5	C16B—C15B—H15B	119.7
C15A—C16A—C11A	119.51 (15)	C11B—C16B—C15B	120.19 (17)
C15A—C16A—H16A	120.2	C11B—C16B—H16B	119.9
C11A—C16A—H16A	120.2	C15B—C16B—H16B	119.9
N22A—C21A—C26A	122.64 (13)	N22B—C21B—C26B	122.49 (15)
N22A—C21A—N1A	113.16 (12)	N22B—C21B—N1B	113.14 (12)
C26A—C21A—N1A	124.19 (13)	C26B—C21B—N1B	124.35 (15)
C21A—N22A—C23A	117.37 (13)	C23B—N22B—C21B	117.57 (13)
N22A—C23A—C24A	123.90 (16)	N22B—C23B—C24B	123.71 (16)
N22A—C23A—H23A	118.1	N22B—C23B—H23B	118.1
C24A—C23A—H23A	118.1	C24B—C23B—H23B	118.1
C23A—C24A—C25A	117.92 (15)	C25B—C24B—C23B	117.88 (16)
C23A—C24A—H24A	121.0	C25B—C24B—H24B	121.1
C25A—C24A—H24A	121.0	C23B—C24B—H24B	121.1
C24A—C25A—C26A	120.10 (15)	C24B—C25B—C26B	120.01 (16)
C24A—C25A—H25A	119.9	C24B—C25B—H25B	120.0
C26A—C25A—H25A	119.9	C26B—C25B—H25B	120.0
C25A—C26A—C21A	117.98 (15)	C25B—C26B—C21B	118.31 (17)
C25A—C26A—H26A	121.0	C25B—C26B—H26B	120.8
C21A—C26A—H26A	121.0	C21B—C26B—H26B	120.8
O1A—C1A—N1A—C21A	9.2 (3)	O1B—C1B—N1B—C21B	4.4 (4)
C11A—C1A—N1A—C21A	−168.63 (13)	C11B—C1B—N1B—C21B	−174.48 (16)
O1A—C1A—C11A—C16A	134.13 (17)	O1B—C1B—C11B—C16B	137.5 (2)
N1A—C1A—C11A—C16A	−47.96 (19)	N1B—C1B—C11B—C16B	−43.6 (3)
O1A—C1A—C11A—C12A	−45.6 (2)	O1B—C1B—C11B—C12B	−40.2 (3)
N1A—C1A—C11A—C12A	132.35 (14)	N1B—C1B—C11B—C12B	138.65 (18)
C16A—C11A—C12A—C13A	1.9 (2)	C16B—C11B—C12B—C13B	1.5 (2)
C1A—C11A—C12A—C13A	−178.38 (13)	C1B—C11B—C12B—C13B	179.32 (16)
C11A—C12A—C13A—F13A	178.83 (14)	C11B—C12B—C13B—C14B	−0.9 (3)
C11A—C12A—C13A—C14A	−2.1 (2)	C11B—C12B—C13B—F13B	179.57 (16)
F13A—C13A—C14A—C15A	179.61 (16)	F13B—C13B—C14B—C15B	179.05 (17)
C12A—C13A—C14A—C15A	0.5 (3)	C12B—C13B—C14B—C15B	−0.5 (3)
C13A—C14A—C15A—C16A	1.2 (3)	C13B—C14B—C15B—C16B	1.2 (3)
C14A—C15A—C16A—C11A	−1.3 (2)	C12B—C11B—C16B—C15B	−0.8 (3)
C12A—C11A—C16A—C15A	−0.3 (2)	C1B—C11B—C16B—C15B	−178.52 (16)
C1A—C11A—C16A—C15A	−179.96 (14)	C14B—C15B—C16B—C11B	−0.6 (3)
C1A—N1A—C21A—N22A	159.10 (14)	C1B—N1B—C21B—N22B	172.50 (17)
C1A—N1A—C21A—C26A	−20.0 (2)	C1B—N1B—C21B—C26B	−6.0 (3)
C26A—C21A—N22A—C23A	3.1 (2)	C26B—C21B—N22B—C23B	1.8 (2)
N1A—C21A—N22A—C23A	−176.05 (14)	N1B—C21B—N22B—C23B	−176.72 (13)
C21A—N22A—C23A—C24A	−0.8 (3)	C21B—N22B—C23B—C24B	−1.5 (2)
N22A—C23A—C24A—C25A	−1.7 (3)	N22B—C23B—C24B—C25B	0.1 (3)
C23A—C24A—C25A—C26A	1.9 (3)	C23B—C24B—C25B—C26B	1.2 (3)
C24A—C25A—C26A—C21A	0.2 (2)	C24B—C25B—C26B—C21B	−0.9 (3)
N22A—C21A—C26A—C25A	−2.9 (2)	N22B—C21B—C26B—C25B	−0.6 (3)
N1A—C21A—C26A—C25A	176.20 (14)	N1B—C21B—C26B—C25B	177.76 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N22B	0.876 (18)	2.199 (18)	3.0721 (17)	174.1 (15)
N1B—H1B···N22A	0.870 (17)	2.183 (18)	3.0502 (18)	174.9 (15)
C26A—H26A···O1A	0.93	2.30	2.844 (2)	117
C26B—H26B···O1B	0.93	2.25	2.836 (3)	120
C25A—H25A···O1B^i	0.93	2.33	3.235 (2)	163

Symmetry code: (i) x, y+1, z.

(Foo-10-128) 2-Fluoro-N-(pyridin-2-yl)benzamide

Crystal data

C12H9FN2O	Z = 4
Mr = 216.21	F(000) = 448
Triclinic, P1	Dx = 1.369 Mg m^−3
Hall symbol: -P 1	Melting point: 358 K
a = 9.7560 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7699 (5) Å	Cell parameters from 5781 reflections
c = 11.9694 (2) Å	θ = 2.6–27.5°
α = 64.412 (4)°	µ = 0.10 mm^−1
β = 68.453 (4)°	T = 294 K
γ = 86.091 (4)°	Block, colourless
V = 1048.88 (7) Å^3	0.42 × 0.35 × 0.28 mm

Data collection

Xcalibur, Sapphire3, Gemini Ultra diffractometer	4377 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.012
Graphite monochromator	θmax = 29.5°, θmin = 2.2°
ω scans	h = −13→11
Absorption correction: analytical (ABSFAC, Clark and Reid, 1998)	k = −12→14
Tmin = 0.959, Tmax = 0.972	l = −16→16
9959 measured reflections	9959 standard reflections every 60 min
5437 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0447P)^2 + 0.216P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
5437 reflections	Δρmax = 0.31 e Å^−3
298 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.035 (3)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F12A	0.44608 (10)	0.15810 (11)	0.99747 (10)	0.0817 (3)
O1A	0.14647 (19)	0.36665 (12)	1.05131 (13)	0.0859 (4)
C1A	0.17178 (16)	0.26512 (13)	1.03041 (13)	0.0466 (3)
N1A	0.17746 (13)	0.25815 (11)	0.91872 (11)	0.0433 (2)
H1A	0.1905 (17)	0.1788 (17)	0.9155 (15)	0.052 (4)*
C11A	0.19731 (14)	0.13474 (12)	1.13396 (12)	0.0407 (3)
C12A	0.33450 (15)	0.08708 (14)	1.11610 (14)	0.0493 (3)
C13A	0.36249 (18)	−0.02679 (16)	1.21334 (17)	0.0597 (4)
H13A	0.4570	−0.0554	1.1981	0.072*
C14A	0.24829 (19)	−0.09719 (15)	1.33315 (16)	0.0604 (4)
H14A	0.2651	−0.1746	1.4001	0.073*
C15A	0.10918 (19)	−0.05416 (16)	1.35487 (15)	0.0590 (4)
H15A	0.0317	−0.1035	1.4359	0.071*
C16A	0.08369 (16)	0.06220 (14)	1.25678 (14)	0.0500 (3)
H16A	−0.0103	0.0921	1.2732	0.060*
C21A	0.15369 (13)	0.36230 (12)	0.80825 (12)	0.0398 (3)
N22A	0.17228 (12)	0.32449 (11)	0.71143 (10)	0.0449 (2)
C23A	0.14592 (16)	0.41515 (15)	0.60424 (14)	0.0524 (3)
H23A	0.1572	0.3894	0.5368	0.063*
C24A	0.10321 (18)	0.54368 (15)	0.58823 (15)	0.0581 (4)
H24A	0.0856	0.6035	0.5123	0.070*
C25A	0.08719 (19)	0.58147 (14)	0.68810 (16)	0.0607 (4)
H25A	0.0594	0.6685	0.6797	0.073*
C26A	0.11215 (17)	0.49101 (13)	0.80038 (14)	0.0517 (3)
H26A	0.1016	0.5151	0.8687	0.062*
F12B	0.50683 (11)	0.29122 (10)	0.54275 (10)	0.0708 (3)
O1B	0.32217 (15)	−0.03366 (11)	0.55100 (11)	0.0693 (3)
C1B	0.32722 (15)	0.06731 (14)	0.57071 (13)	0.0458 (3)
N1B	0.29127 (13)	0.06240 (11)	0.69386 (11)	0.0462 (3)
H1B	0.2719 (17)	0.1386 (17)	0.7022 (15)	0.054 (4)*
C11B	0.36783 (14)	0.21001 (13)	0.45761 (13)	0.0446 (3)
C12B	0.45352 (15)	0.31498 (15)	0.44635 (14)	0.0506 (3)
C13B	0.48772 (18)	0.44457 (17)	0.34028 (17)	0.0653 (4)
H13B	0.5457	0.5130	0.3357	0.078*
C14B	0.4347 (2)	0.47132 (18)	0.24110 (18)	0.0731 (5)
H14B	0.4564	0.5587	0.1692	0.088*
C15B	0.3500 (2)	0.36969 (18)	0.24784 (17)	0.0697 (4)
H15B	0.3143	0.3882	0.1807	0.084*
C16B	0.31819 (18)	0.24044 (16)	0.35404 (14)	0.0559 (3)
H16B	0.2623	0.1718	0.3569	0.067*
C21B	0.25986 (14)	−0.05504 (12)	0.81614 (13)	0.0412 (3)
N22B	0.20880 (13)	−0.02642 (11)	0.92156 (11)	0.0463 (3)
C23B	0.17916 (17)	−0.13237 (14)	1.04274 (14)	0.0513 (3)
H23B	0.1417	−0.1139	1.1169	0.062*
C24B	0.20098 (17)	−0.26650 (14)	1.06348 (15)	0.0540 (3)
H24B	0.1809	−0.3369	1.1491	0.065*
C25B	0.25350 (19)	−0.29377 (14)	0.95390 (16)	0.0604 (4)
H25B	0.2689	−0.3838	0.9650	0.072*
C26B	0.28339 (18)	−0.18834 (14)	0.82792 (15)	0.0552 (3)
H26B	0.3182	−0.2055	0.7530	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F12A	0.0523 (5)	0.0801 (7)	0.0734 (6)	0.0050 (5)	−0.0019 (5)	−0.0170 (5)
O1A	0.1636 (14)	0.0540 (6)	0.0800 (8)	0.0451 (8)	−0.0752 (9)	−0.0445 (6)
C1A	0.0591 (8)	0.0405 (6)	0.0484 (7)	0.0112 (6)	−0.0254 (6)	−0.0233 (6)
N1A	0.0579 (7)	0.0340 (5)	0.0437 (6)	0.0120 (5)	−0.0229 (5)	−0.0198 (4)
C11A	0.0479 (7)	0.0390 (6)	0.0425 (6)	0.0070 (5)	−0.0209 (5)	−0.0214 (5)
C12A	0.0451 (7)	0.0486 (7)	0.0500 (7)	0.0037 (5)	−0.0151 (6)	−0.0200 (6)
C13A	0.0547 (8)	0.0564 (8)	0.0763 (10)	0.0170 (7)	−0.0368 (8)	−0.0279 (8)
C14A	0.0794 (11)	0.0473 (8)	0.0591 (9)	0.0080 (7)	−0.0407 (8)	−0.0153 (7)
C15A	0.0682 (10)	0.0531 (8)	0.0440 (7)	−0.0044 (7)	−0.0155 (7)	−0.0143 (6)
C16A	0.0468 (7)	0.0533 (8)	0.0512 (7)	0.0062 (6)	−0.0163 (6)	−0.0257 (6)
C21A	0.0413 (6)	0.0353 (6)	0.0417 (6)	0.0060 (5)	−0.0156 (5)	−0.0161 (5)
N22A	0.0512 (6)	0.0433 (6)	0.0434 (6)	0.0124 (5)	−0.0200 (5)	−0.0209 (5)
C23A	0.0609 (8)	0.0545 (8)	0.0457 (7)	0.0154 (6)	−0.0245 (6)	−0.0229 (6)
C24A	0.0708 (10)	0.0479 (7)	0.0522 (8)	0.0143 (7)	−0.0307 (7)	−0.0139 (6)
C25A	0.0812 (11)	0.0380 (7)	0.0658 (9)	0.0183 (7)	−0.0355 (8)	−0.0206 (7)
C26A	0.0691 (9)	0.0384 (6)	0.0531 (8)	0.0132 (6)	−0.0272 (7)	−0.0223 (6)
F12B	0.0692 (6)	0.0755 (6)	0.0790 (6)	−0.0043 (5)	−0.0406 (5)	−0.0315 (5)
O1B	0.1119 (10)	0.0497 (6)	0.0601 (6)	0.0080 (6)	−0.0360 (6)	−0.0329 (5)
C1B	0.0519 (7)	0.0451 (7)	0.0482 (7)	0.0079 (5)	−0.0209 (6)	−0.0258 (6)
N1B	0.0619 (7)	0.0362 (5)	0.0448 (6)	0.0094 (5)	−0.0201 (5)	−0.0220 (5)
C11B	0.0455 (7)	0.0471 (7)	0.0434 (7)	0.0074 (5)	−0.0146 (5)	−0.0238 (6)
C12B	0.0432 (7)	0.0565 (8)	0.0538 (8)	0.0037 (6)	−0.0171 (6)	−0.0264 (6)
C13B	0.0543 (9)	0.0564 (9)	0.0708 (10)	−0.0091 (7)	−0.0141 (8)	−0.0210 (8)
C14B	0.0781 (11)	0.0573 (9)	0.0592 (10)	−0.0015 (8)	−0.0197 (9)	−0.0078 (8)
C15B	0.0865 (12)	0.0677 (10)	0.0530 (9)	0.0081 (9)	−0.0336 (9)	−0.0187 (8)
C16B	0.0670 (9)	0.0567 (8)	0.0504 (8)	0.0048 (7)	−0.0254 (7)	−0.0259 (7)
C21B	0.0433 (6)	0.0367 (6)	0.0467 (7)	0.0049 (5)	−0.0186 (5)	−0.0196 (5)
N22B	0.0577 (7)	0.0374 (5)	0.0451 (6)	0.0043 (5)	−0.0191 (5)	−0.0193 (5)
C23B	0.0615 (8)	0.0437 (7)	0.0453 (7)	−0.0008 (6)	−0.0175 (6)	−0.0177 (6)
C24B	0.0586 (8)	0.0403 (7)	0.0533 (8)	−0.0001 (6)	−0.0217 (7)	−0.0108 (6)
C25B	0.0729 (10)	0.0356 (7)	0.0699 (10)	0.0106 (6)	−0.0272 (8)	−0.0210 (7)
C26B	0.0698 (9)	0.0423 (7)	0.0582 (8)	0.0129 (6)	−0.0230 (7)	−0.0280 (6)

Geometric parameters (Å, º)

F12A—C12A	1.3515 (16)	F12B—C12B	1.3547 (16)
O1A—C1A	1.2138 (15)	O1B—C1B	1.2158 (15)
C1A—N1A	1.3519 (16)	C1B—N1B	1.3616 (16)
C1A—C11A	1.4986 (17)	C1B—C11B	1.4979 (19)
N1A—C21A	1.4032 (15)	N1B—C21B	1.4000 (16)
N1A—H1A	0.871 (16)	N1B—H1B	0.870 (16)
C11A—C12A	1.3754 (18)	C11B—C12B	1.3818 (19)
C11A—C16A	1.3890 (18)	C11B—C16B	1.3954 (19)
C12A—C13A	1.374 (2)	C12B—C13B	1.376 (2)
C13A—C14A	1.369 (2)	C13B—C14B	1.377 (2)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.372 (2)	C14B—C15B	1.373 (3)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—C16A	1.383 (2)	C15B—C16B	1.375 (2)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—H16A	0.9300	C16B—H16B	0.9300
C21A—N22A	1.3360 (15)	C21B—N22B	1.3373 (16)
C21A—C26A	1.3904 (17)	C21B—C26B	1.3920 (17)
N22A—C23A	1.3385 (16)	N22B—C23B	1.3404 (17)
C23A—C24A	1.370 (2)	C23B—C24B	1.3715 (19)
C23A—H23A	0.9300	C23B—H23B	0.9300
C24A—C25A	1.376 (2)	C24B—C25B	1.374 (2)
C24A—H24A	0.9300	C24B—H24B	0.9300
C25A—C26A	1.375 (2)	C25B—C26B	1.375 (2)
C25A—H25A	0.9300	C25B—H25B	0.9300
C26A—H26A	0.9300	C26B—H26B	0.9300
O1A—C1A—N1A	124.86 (12)	O1B—C1B—N1B	124.18 (13)
O1A—C1A—C11A	119.68 (12)	O1B—C1B—C11B	120.95 (12)
N1A—C1A—C11A	115.45 (10)	N1B—C1B—C11B	114.81 (11)
C1A—N1A—C21A	127.63 (10)	C1B—N1B—C21B	127.86 (11)
C1A—N1A—H1A	117.9 (10)	C1B—N1B—H1B	118.1 (10)
C21A—N1A—H1A	114.3 (10)	C21B—N1B—H1B	113.4 (10)
C12A—C11A—C16A	117.21 (12)	C12B—C11B—C16B	116.72 (13)
C12A—C11A—C1A	122.16 (12)	C12B—C11B—C1B	124.88 (12)
C16A—C11A—C1A	120.49 (12)	C16B—C11B—C1B	118.40 (12)
F12A—C12A—C13A	119.37 (13)	F12B—C12B—C13B	117.83 (13)
F12A—C12A—C11A	117.57 (12)	F12B—C12B—C11B	119.51 (13)
C13A—C12A—C11A	123.05 (13)	C13B—C12B—C11B	122.65 (14)
C14A—C13A—C12A	118.59 (14)	C12B—C13B—C14B	118.93 (15)
C14A—C13A—H13A	120.7	C12B—C13B—H13B	120.5
C12A—C13A—H13A	120.7	C14B—C13B—H13B	120.5
C13A—C14A—C15A	120.34 (14)	C15B—C14B—C13B	120.34 (16)
C13A—C14A—H14A	119.8	C15B—C14B—H14B	119.8
C15A—C14A—H14A	119.8	C13B—C14B—H14B	119.8
C14A—C15A—C16A	120.26 (14)	C14B—C15B—C16B	119.86 (16)
C14A—C15A—H15A	119.9	C14B—C15B—H15B	120.1
C16A—C15A—H15A	119.9	C16B—C15B—H15B	120.1
C15A—C16A—C11A	120.52 (13)	C15B—C16B—C11B	121.49 (15)
C15A—C16A—H16A	119.7	C15B—C16B—H16B	119.3
C11A—C16A—H16A	119.7	C11B—C16B—H16B	119.3
N22A—C21A—C26A	122.99 (11)	N22B—C21B—C26B	122.80 (12)
N22A—C21A—N1A	113.10 (10)	N22B—C21B—N1B	113.34 (10)
C26A—C21A—N1A	123.90 (11)	C26B—C21B—N1B	123.83 (12)
C21A—N22A—C23A	117.39 (11)	C21B—N22B—C23B	117.48 (11)
N22A—C23A—C24A	123.76 (13)	N22B—C23B—C24B	123.65 (13)
N22A—C23A—H23A	118.1	N22B—C23B—H23B	118.2
C24A—C23A—H23A	118.1	C24B—C23B—H23B	118.2
C23A—C24A—C25A	117.90 (13)	C23B—C24B—C25B	117.98 (13)
C23A—C24A—H24A	121.1	C23B—C24B—H24B	121.0
C25A—C24A—H24A	121.1	C25B—C24B—H24B	121.0
C26A—C25A—C24A	120.20 (13)	C24B—C25B—C26B	120.23 (13)
C26A—C25A—H25A	119.9	C24B—C25B—H25B	119.9
C24A—C25A—H25A	119.9	C26B—C25B—H25B	119.9
C25A—C26A—C21A	117.74 (13)	C25B—C26B—C21B	117.86 (13)
C25A—C26A—H26A	121.1	C25B—C26B—H26B	121.1
C21A—C26A—H26A	121.1	C21B—C26B—H26B	121.1
O1A—C1A—N1A—C21A	−1.1 (2)	O1B—C1B—N1B—C21B	8.1 (2)
C11A—C1A—N1A—C21A	178.01 (12)	C11B—C1B—N1B—C21B	−174.76 (12)
O1A—C1A—C11A—C12A	−109.55 (17)	O1B—C1B—C11B—C12B	−142.07 (15)
N1A—C1A—C11A—C12A	71.26 (17)	N1B—C1B—C11B—C12B	40.69 (18)
O1A—C1A—C11A—C16A	65.87 (19)	O1B—C1B—C11B—C16B	36.9 (2)
N1A—C1A—C11A—C16A	−113.32 (14)	N1B—C1B—C11B—C16B	−140.30 (13)
C16A—C11A—C12A—F12A	−179.19 (12)	C16B—C11B—C12B—F12B	−179.06 (12)
C1A—C11A—C12A—F12A	−3.63 (19)	C1B—C11B—C12B—F12B	0.0 (2)
C16A—C11A—C12A—C13A	−0.2 (2)	C16B—C11B—C12B—C13B	1.0 (2)
C1A—C11A—C12A—C13A	175.36 (13)	C1B—C11B—C12B—C13B	−179.98 (13)
F12A—C12A—C13A—C14A	179.73 (14)	F12B—C12B—C13B—C14B	−179.94 (15)
C11A—C12A—C13A—C14A	0.8 (2)	C11B—C12B—C13B—C14B	0.0 (2)
C12A—C13A—C14A—C15A	−0.1 (2)	C12B—C13B—C14B—C15B	−0.5 (3)
C13A—C14A—C15A—C16A	−1.2 (2)	C13B—C14B—C15B—C16B	−0.1 (3)
C14A—C15A—C16A—C11A	1.7 (2)	C14B—C15B—C16B—C11B	1.2 (3)
C12A—C11A—C16A—C15A	−1.05 (19)	C12B—C11B—C16B—C15B	−1.6 (2)
C1A—C11A—C16A—C15A	−176.69 (12)	C1B—C11B—C16B—C15B	179.31 (14)
C1A—N1A—C21A—N22A	177.88 (13)	C1B—N1B—C21B—N22B	−171.38 (13)
C1A—N1A—C21A—C26A	−3.3 (2)	C1B—N1B—C21B—C26B	10.6 (2)
C26A—C21A—N22A—C23A	−1.5 (2)	C26B—C21B—N22B—C23B	−0.3 (2)
N1A—C21A—N22A—C23A	177.29 (12)	N1B—C21B—N22B—C23B	−178.40 (12)
C21A—N22A—C23A—C24A	0.8 (2)	C21B—N22B—C23B—C24B	1.3 (2)
N22A—C23A—C24A—C25A	0.3 (2)	N22B—C23B—C24B—C25B	−1.3 (2)
C23A—C24A—C25A—C26A	−0.7 (3)	C23B—C24B—C25B—C26B	0.3 (2)
C24A—C25A—C26A—C21A	0.1 (2)	C24B—C25B—C26B—C21B	0.5 (2)
N22A—C21A—C26A—C25A	1.1 (2)	N22B—C21B—C26B—C25B	−0.5 (2)
N1A—C21A—C26A—C25A	−177.61 (14)	N1B—C21B—C26B—C25B	177.33 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N22B	0.871 (16)	2.177 (16)	3.0460 (14)	175.7 (14)
N1B—H1B···N22A	0.870 (16)	2.193 (16)	3.0408 (15)	164.8 (14)
N1B—H1B···F12B	0.870 (16)	2.487 (16)	2.7981 (15)	101.8 (12)
C26A—H26A···O1A	0.93	2.26	2.8513 (18)	121
C26B—H26B···O1B	0.93	2.31	2.8810 (19)	119