Download citation
Download citation
link to html
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; Npyridine 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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768112006799/gp5047sup1.cif
Contains datablocks global, Fpp-10-124, Fmp-10-126, Fop-10-125, Fpm_O-10-127, Fpm_N-10-121, Fmm-10-122, Fom_O-11-009, Fom_F-11-061, Fpo-10-123, Fmo-11-003, Foo-10-128

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112006799/gp5047Fpp-10-124sup2.hkl
Contains datablock Fpp-10-124

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112006799/gp5047Fmp-10-126sup3.hkl
Contains datablock Fmp-10-126

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112006799/gp5047Fop-10-125sup4.hkl
Contains datablock Fop-10-125

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112006799/gp5047Fpm_N-10-121sup5.hkl
Contains datablock Fpm_N-10-121

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112006799/gp5047Fpm_O-10-127sup6.hkl
Contains datablock Fpm_O-10-127

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112006799/gp5047Fmm-10-122sup7.hkl
Contains datablock Fmm-10-122

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112006799/gp5047Fom_O-11-009sup8.hkl
Contains datablock Fom_O-11-009

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112006799/gp5047Fom_F-11-061sup9.hkl
Contains datablock Fom_F-11-061

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112006799/gp5047Fpo-10-123sup10.hkl
Contains datablock Fpo-10-123

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112006799/gp5047Fmo-11-003sup11.hkl
Contains datablock Fmo-11-003

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112006799/gp5047Foo-10-128sup12.hkl
Contains datablock Foo-10-128

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768112006799/gp5047sup13.pdf
NMR and spectroscopic data

CCDC references: 865570; 865571; 865572; 865573; 865574; 865575; 865576; 865577; 865578; 865579; 865580

Comment top

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 top

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.

Experimental top

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

Refinement top

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 Uiso(H) = 1.2Ueq(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 top

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 top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
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 top
Crystal data top
C12H9FN2OF(000) = 448
Mr = 216.21Dx = 1.427 Mg m3
Monoclinic, P21/cMelting point: 461 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 5.6777 (1) ÅCell parameters from 5255 reflections
b = 11.4769 (2) Åθ = 2.6–27.5°
c = 15.5289 (3) ŵ = 0.11 mm1
β = 95.974 (2)°T = 294 K
V = 1006.40 (3) Å3Block, colourless
Z = 40.39 × 0.25 × 0.19 mm
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
1979 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.013
Graphite monochromatorθmax = 27.8°, θmin = 2.6°
ω scansh = 77
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
k = 1514
Tmin = 0.960, Tmax = 0.980l = 1919
7351 measured reflections7599 standard reflections every 60 min
2216 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.0388P)2 + 0.2424P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2216 reflectionsΔρmax = 0.20 e Å3
150 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.029 (3)
Crystal data top
C12H9FN2OV = 1006.40 (3) Å3
Mr = 216.21Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.6777 (1) ŵ = 0.11 mm1
b = 11.4769 (2) ÅT = 294 K
c = 15.5289 (3) Å0.39 × 0.25 × 0.19 mm
β = 95.974 (2)°
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
1979 reflections with I > 2σ(I)
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
Rint = 0.013
Tmin = 0.960, Tmax = 0.9807599 standard reflections every 60 min
7351 measured reflections intensity decay: 1%
2216 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.20 e Å3
2216 reflectionsΔρmin = 0.14 e Å3
150 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
F140.87229 (18)0.45954 (8)0.64358 (6)0.0755 (3)
O11.09479 (15)0.04913 (8)0.40012 (6)0.0476 (2)
C10.9023 (2)0.09065 (10)0.41083 (7)0.0341 (2)
N10.69275 (19)0.05257 (9)0.36941 (7)0.0412 (3)
H10.580 (3)0.1009 (14)0.3682 (10)0.056 (4)*
C110.88200 (19)0.19020 (9)0.47152 (7)0.0329 (2)
C121.0667 (2)0.26980 (10)0.48104 (7)0.0374 (3)
H121.19450.26120.44860.045*
C131.0623 (2)0.36165 (11)0.53823 (8)0.0441 (3)
H131.18410.41610.54420.053*
C140.8731 (2)0.37027 (11)0.58611 (8)0.0470 (3)
C150.6888 (2)0.29287 (12)0.57928 (8)0.0476 (3)
H150.56410.30110.61320.057*
C160.6921 (2)0.20211 (11)0.52079 (8)0.0400 (3)
H160.56760.14910.51440.048*
C210.6588 (2)0.04089 (10)0.31169 (7)0.0341 (3)
C220.4453 (2)0.04844 (11)0.25949 (8)0.0421 (3)
H220.32850.00770.26300.051*
C230.4089 (2)0.13984 (12)0.20268 (9)0.0468 (3)
H230.26540.14290.16790.056*
N240.56608 (19)0.22482 (9)0.19388 (7)0.0445 (3)
C250.7683 (2)0.21652 (10)0.24539 (8)0.0409 (3)
H250.88060.27470.24120.049*
C260.8241 (2)0.12859 (10)0.30433 (7)0.0378 (3)
H260.96890.12790.33840.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F140.0856 (7)0.0658 (6)0.0754 (6)0.0075 (5)0.0098 (5)0.0398 (5)
O10.0405 (5)0.0442 (5)0.0590 (6)0.0031 (4)0.0094 (4)0.0136 (4)
C10.0400 (6)0.0309 (5)0.0313 (5)0.0040 (4)0.0031 (4)0.0010 (4)
N10.0406 (5)0.0393 (5)0.0417 (5)0.0114 (4)0.0049 (4)0.0106 (4)
C110.0366 (5)0.0327 (5)0.0283 (5)0.0071 (4)0.0018 (4)0.0011 (4)
C120.0393 (6)0.0374 (6)0.0354 (6)0.0046 (5)0.0031 (4)0.0011 (5)
C130.0469 (7)0.0360 (6)0.0478 (7)0.0009 (5)0.0024 (5)0.0036 (5)
C140.0555 (7)0.0427 (7)0.0415 (7)0.0134 (6)0.0022 (5)0.0127 (5)
C150.0433 (7)0.0573 (8)0.0429 (7)0.0133 (6)0.0073 (5)0.0074 (6)
C160.0368 (6)0.0433 (6)0.0392 (6)0.0044 (5)0.0014 (5)0.0017 (5)
C210.0394 (6)0.0330 (6)0.0299 (5)0.0005 (4)0.0040 (4)0.0011 (4)
C220.0356 (6)0.0439 (7)0.0466 (7)0.0039 (5)0.0031 (5)0.0073 (5)
C230.0374 (6)0.0531 (8)0.0487 (7)0.0034 (5)0.0012 (5)0.0114 (6)
N240.0457 (6)0.0424 (6)0.0454 (6)0.0046 (4)0.0048 (4)0.0113 (5)
C250.0457 (6)0.0337 (6)0.0436 (6)0.0030 (5)0.0057 (5)0.0035 (5)
C260.0410 (6)0.0352 (6)0.0361 (6)0.0043 (5)0.0014 (5)0.0006 (5)
Geometric parameters (Å, º) top
F14—C141.3591 (14)C15—C161.3835 (17)
O1—C11.2195 (14)C15—H150.9300
C1—N11.3641 (15)C16—H160.9300
C1—C111.4931 (15)C21—C261.3888 (16)
N1—C211.3983 (14)C21—C221.3894 (16)
N1—H10.848 (16)C22—C231.3724 (17)
C11—C121.3871 (16)C22—H220.9300
C11—C161.3921 (16)C23—N241.3386 (16)
C12—C131.3803 (16)C23—H230.9300
C12—H120.9300N24—C251.3327 (16)
C13—C141.3722 (19)C25—C261.3770 (16)
C13—H130.9300C25—H250.9300
C14—C151.368 (2)C26—H260.9300
O1—C1—N1124.09 (11)C16—C15—H15120.8
O1—C1—C11120.94 (10)C15—C16—C11119.94 (11)
N1—C1—C11114.96 (9)C15—C16—H16120.0
C1—N1—C21127.10 (10)C11—C16—H16120.0
C1—N1—H1115.0 (11)C26—C21—C22117.58 (10)
C21—N1—H1115.7 (11)C26—C21—N1124.03 (10)
C12—C11—C16119.80 (10)C22—C21—N1118.38 (10)
C12—C11—C1117.65 (10)C23—C22—C21119.10 (11)
C16—C11—C1122.48 (10)C23—C22—H22120.4
C13—C12—C11120.49 (11)C21—C22—H22120.4
C13—C12—H12119.8N24—C23—C22124.42 (11)
C11—C12—H12119.8N24—C23—H23117.8
C14—C13—C12118.12 (12)C22—C23—H23117.8
C14—C13—H13120.9C25—N24—C23115.38 (10)
C12—C13—H13120.9N24—C25—C26125.13 (11)
F14—C14—C15119.05 (12)N24—C25—H25117.4
F14—C14—C13117.80 (13)C26—C25—H25117.4
C15—C14—C13123.14 (11)C25—C26—C21118.37 (11)
C14—C15—C16118.49 (11)C25—C26—H26120.8
C14—C15—H15120.8C21—C26—H26120.8
O1—C1—N1—C212.8 (2)C14—C15—C16—C110.96 (18)
C11—C1—N1—C21177.77 (10)C12—C11—C16—C150.28 (17)
O1—C1—C11—C1231.87 (16)C1—C11—C16—C15176.64 (11)
N1—C1—C11—C12147.60 (11)C1—N1—C21—C2617.61 (19)
O1—C1—C11—C16145.11 (12)C1—N1—C21—C22163.76 (12)
N1—C1—C11—C1635.41 (15)C26—C21—C22—C231.08 (18)
C16—C11—C12—C130.82 (17)N1—C21—C22—C23179.80 (11)
C1—C11—C12—C13177.89 (10)C21—C22—C23—N240.6 (2)
C11—C12—C13—C141.20 (18)C22—C23—N24—C250.27 (19)
C12—C13—C14—F14178.68 (11)C23—N24—C25—C260.59 (18)
C12—C13—C14—C150.5 (2)N24—C25—C26—C210.06 (19)
F14—C14—C15—C16179.75 (11)C22—C21—C26—C250.79 (17)
C13—C14—C15—C160.6 (2)N1—C21—C26—C25179.43 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N24i0.848 (16)2.335 (17)3.0581 (15)143.5 (14)
C26—H26···O10.932.332.8738 (15)117
C26—H26···Cg1ii0.932.773.4183 (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 top
Crystal data top
C12H9FN2OF(000) = 448
Mr = 216.21Dx = 1.442 Mg m3
Monoclinic, P21/cMelting point: 460 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 5.7961 (1) ÅCell parameters from 5573 reflections
b = 11.3050 (2) Åθ = 2.6–27.5°
c = 15.2384 (2) ŵ = 0.11 mm1
β = 94.238 (1)°T = 294 K
V = 995.76 (3) Å3Block, colourless
Z = 40.37 × 0.34 × 0.19 mm
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
1988 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.012
Graphite monochromatorθmax = 27.8°, θmin = 2.7°
ω scansh = 77
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
k = 1414
Tmin = 0.961, Tmax = 0.980l = 1915
7728 measured reflections7983 standard reflections every 60 min
2202 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.041P)2 + 0.2546P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2202 reflectionsΔρmax = 0.24 e Å3
150 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.010 (2)
Crystal data top
C12H9FN2OV = 995.76 (3) Å3
Mr = 216.21Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.7961 (1) ŵ = 0.11 mm1
b = 11.3050 (2) ÅT = 294 K
c = 15.2384 (2) Å0.37 × 0.34 × 0.19 mm
β = 94.238 (1)°
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
1988 reflections with I > 2σ(I)
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
Rint = 0.012
Tmin = 0.961, Tmax = 0.9807983 standard reflections every 60 min
7728 measured reflections intensity decay: 1%
2202 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.092H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.24 e Å3
2202 reflectionsΔρmin = 0.17 e Å3
150 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
F131.17541 (17)0.44310 (8)0.57107 (7)0.0682 (3)
O11.08628 (14)0.05792 (8)0.40298 (6)0.0424 (2)
C10.89463 (19)0.09679 (10)0.41387 (7)0.0313 (2)
N10.69589 (18)0.05971 (9)0.36815 (7)0.0369 (2)
H10.581 (3)0.1067 (14)0.3687 (10)0.046 (4)*
C110.85955 (19)0.19237 (10)0.47948 (7)0.0316 (2)
C121.0360 (2)0.27466 (10)0.49496 (8)0.0364 (3)
H121.16970.27100.46480.044*
C131.0067 (2)0.36146 (11)0.55610 (9)0.0444 (3)
C140.8139 (3)0.36913 (13)0.60300 (9)0.0524 (4)
H140.79940.42920.64390.063*
C150.6427 (2)0.28571 (14)0.58796 (9)0.0502 (3)
H150.51210.28860.61990.060*
C160.6625 (2)0.19779 (12)0.52609 (8)0.0406 (3)
H160.54470.14260.51570.049*
C210.67165 (19)0.03339 (9)0.30790 (7)0.0308 (2)
C220.4639 (2)0.04292 (10)0.25615 (8)0.0372 (3)
H220.34720.01260.26100.045*
C230.4337 (2)0.13541 (11)0.19793 (8)0.0412 (3)
H230.29450.13960.16350.049*
N240.59093 (18)0.21993 (9)0.18739 (7)0.0405 (3)
C250.7890 (2)0.20900 (10)0.23757 (8)0.0380 (3)
H250.90180.26630.23160.046*
C260.83920 (19)0.11932 (10)0.29759 (7)0.0348 (3)
H260.98120.11650.33020.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F130.0714 (6)0.0470 (5)0.0830 (7)0.0086 (4)0.0148 (5)0.0205 (4)
O10.0360 (4)0.0400 (5)0.0516 (5)0.0009 (3)0.0067 (4)0.0102 (4)
C10.0368 (6)0.0276 (5)0.0296 (5)0.0013 (4)0.0025 (4)0.0021 (4)
N10.0369 (5)0.0340 (5)0.0390 (5)0.0088 (4)0.0034 (4)0.0081 (4)
C110.0373 (6)0.0298 (5)0.0271 (5)0.0056 (4)0.0019 (4)0.0018 (4)
C120.0398 (6)0.0345 (6)0.0341 (6)0.0036 (5)0.0019 (5)0.0005 (5)
C130.0532 (7)0.0339 (6)0.0437 (7)0.0029 (5)0.0130 (6)0.0053 (5)
C140.0672 (9)0.0486 (8)0.0404 (7)0.0193 (7)0.0037 (6)0.0143 (6)
C150.0510 (7)0.0598 (9)0.0406 (7)0.0156 (6)0.0078 (6)0.0060 (6)
C160.0404 (6)0.0442 (7)0.0374 (6)0.0041 (5)0.0036 (5)0.0002 (5)
C210.0361 (5)0.0285 (5)0.0280 (5)0.0003 (4)0.0035 (4)0.0012 (4)
C220.0345 (6)0.0348 (6)0.0418 (6)0.0044 (5)0.0000 (5)0.0021 (5)
C230.0376 (6)0.0418 (7)0.0428 (6)0.0010 (5)0.0055 (5)0.0045 (5)
N240.0437 (6)0.0383 (5)0.0390 (5)0.0008 (4)0.0003 (4)0.0079 (4)
C250.0402 (6)0.0347 (6)0.0392 (6)0.0052 (5)0.0031 (5)0.0044 (5)
C260.0347 (6)0.0349 (6)0.0343 (6)0.0033 (5)0.0011 (4)0.0020 (5)
Geometric parameters (Å, º) top
F13—C131.3517 (16)C15—C161.3805 (18)
O1—C11.2173 (13)C15—H150.9300
C1—N11.3672 (15)C16—H160.9300
C1—C111.4962 (15)C21—C261.3908 (15)
N1—C211.3968 (14)C21—C221.3938 (16)
N1—H10.852 (15)C22—C231.3742 (17)
C11—C121.3898 (16)C22—H220.9300
C11—C161.3904 (16)C23—N241.3383 (16)
C12—C131.3724 (17)C23—H230.9300
C12—H120.9300N24—C251.3371 (16)
C13—C141.373 (2)C25—C261.3819 (16)
C14—C151.376 (2)C25—H250.9300
C14—H140.9300C26—H260.9300
O1—C1—N1124.25 (10)C16—C15—H15119.6
O1—C1—C11121.48 (10)C15—C16—C11119.56 (12)
N1—C1—C11114.27 (9)C15—C16—H16120.2
C1—N1—C21127.30 (10)C11—C16—H16120.2
C1—N1—H1115.6 (10)C26—C21—C22117.60 (10)
C21—N1—H1115.9 (10)C26—C21—N1124.29 (10)
C12—C11—C16120.39 (11)C22—C21—N1118.09 (10)
C12—C11—C1117.53 (10)C23—C22—C21119.20 (11)
C16—C11—C1122.04 (11)C23—C22—H22120.4
C13—C12—C11117.86 (11)C21—C22—H22120.4
C13—C12—H12121.1N24—C23—C22124.41 (11)
C11—C12—H12121.1N24—C23—H23117.8
F13—C13—C12118.58 (13)C22—C23—H23117.8
F13—C13—C14118.39 (12)C25—N24—C23115.40 (10)
C12—C13—C14123.02 (13)N24—C25—C26125.19 (11)
C13—C14—C15118.34 (12)N24—C25—H25117.4
C13—C14—H14120.8C26—C25—H25117.4
C15—C14—H14120.8C25—C26—C21118.20 (10)
C14—C15—C16120.80 (13)C25—C26—H26120.9
C14—C15—H15119.6C21—C26—H26120.9
O1—C1—N1—C215.86 (19)C14—C15—C16—C111.1 (2)
C11—C1—N1—C21174.83 (10)C12—C11—C16—C150.08 (18)
O1—C1—C11—C1231.61 (15)C1—C11—C16—C15177.86 (11)
N1—C1—C11—C12147.72 (10)C1—N1—C21—C2613.64 (18)
O1—C1—C11—C16146.23 (12)C1—N1—C21—C22168.08 (11)
N1—C1—C11—C1634.44 (15)C26—C21—C22—C230.01 (17)
C16—C11—C12—C131.08 (17)N1—C21—C22—C23178.41 (11)
C1—C11—C12—C13178.96 (10)C21—C22—C23—N240.8 (2)
C11—C12—C13—F13179.14 (10)C22—C23—N24—C250.83 (19)
C11—C12—C13—C141.00 (19)C23—N24—C25—C260.17 (18)
F13—C13—C14—C15179.75 (12)N24—C25—C26—C210.53 (19)
C12—C13—C14—C150.1 (2)C22—C21—C26—C250.58 (16)
C13—C14—C15—C161.2 (2)N1—C21—C26—C25177.71 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N24i0.852 (15)2.333 (16)3.0786 (14)146.5 (13)
C26—H26···O10.932.322.8819 (14)118
Symmetry code: (i) x+1, y+1/2, z+1/2.
(Fop-10-125) 2-Fluoro-N-(pyridin-4-yl)benzamide top
Crystal data top
C12H9FN2OF(000) = 448
Mr = 216.21Dx = 1.422 Mg m3
Monoclinic, P21/cMelting point: 408 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 6.0388 (1) ÅCell parameters from 4543 reflections
b = 11.2502 (2) Åθ = 2.6–27.5°
c = 14.9265 (3) ŵ = 0.11 mm1
β = 95.310 (2)°T = 294 K
V = 1009.72 (3) Å3Block, colourless
Z = 40.45 × 0.30 × 0.08 mm
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
1914 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.016
Graphite monochromatorθmax = 27.9°, θmin = 2.3°
ω scansh = 77
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
k = 1414
Tmin = 0.954, Tmax = 0.992l = 1919
7133 measured reflections7343 standard reflections every 60 min
2256 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0515P)2 + 0.2002P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2256 reflectionsΔρmax = 0.23 e Å3
150 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.037 (4)
Crystal data top
C12H9FN2OV = 1009.72 (3) Å3
Mr = 216.21Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.0388 (1) ŵ = 0.11 mm1
b = 11.2502 (2) ÅT = 294 K
c = 14.9265 (3) Å0.45 × 0.30 × 0.08 mm
β = 95.310 (2)°
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
1914 reflections with I > 2σ(I)
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
Rint = 0.016
Tmin = 0.954, Tmax = 0.9927343 standard reflections every 60 min
7133 measured reflections intensity decay: 1%
2256 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.23 e Å3
2256 reflectionsΔρmin = 0.16 e Å3
150 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
F120.53290 (13)0.13954 (8)0.52577 (6)0.0569 (3)
O11.07477 (15)0.05676 (9)0.40003 (7)0.0509 (3)
C10.8959 (2)0.09855 (10)0.41433 (8)0.0339 (3)
N10.69998 (19)0.06499 (10)0.37006 (7)0.0413 (3)
H10.585 (3)0.1091 (16)0.3746 (11)0.060 (5)*
C110.8825 (2)0.19698 (10)0.48148 (7)0.0341 (3)
C120.7071 (2)0.21405 (11)0.53372 (8)0.0406 (3)
C130.7051 (3)0.30451 (14)0.59594 (10)0.0548 (4)
H130.58570.31340.63050.066*
C140.8825 (3)0.38120 (14)0.60592 (10)0.0603 (4)
H140.88230.44340.64700.072*
C151.0608 (3)0.36688 (12)0.55561 (10)0.0526 (4)
H151.18020.41930.56270.063*
C161.0617 (2)0.27447 (11)0.49463 (8)0.0416 (3)
H161.18400.26400.46190.050*
C210.6637 (2)0.02698 (10)0.30768 (7)0.0346 (3)
C220.4564 (2)0.03401 (12)0.25901 (9)0.0445 (3)
H220.34660.02170.26780.053*
C230.4160 (2)0.12456 (13)0.19762 (10)0.0495 (3)
H230.27700.12720.16520.059*
N240.5627 (2)0.20888 (10)0.18154 (8)0.0473 (3)
C250.7594 (2)0.20090 (11)0.22963 (9)0.0427 (3)
H250.86480.25870.22020.051*
C260.8192 (2)0.11361 (11)0.29233 (8)0.0383 (3)
H260.95990.11290.32340.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F120.0477 (5)0.0689 (6)0.0560 (5)0.0074 (4)0.0157 (4)0.0076 (4)
O10.0404 (5)0.0507 (6)0.0628 (6)0.0019 (4)0.0107 (4)0.0180 (5)
C10.0404 (6)0.0301 (5)0.0316 (6)0.0025 (5)0.0058 (5)0.0019 (4)
N10.0401 (6)0.0397 (6)0.0432 (6)0.0094 (5)0.0011 (5)0.0109 (5)
C110.0415 (6)0.0316 (6)0.0287 (5)0.0057 (5)0.0003 (5)0.0017 (4)
C120.0425 (7)0.0432 (7)0.0359 (6)0.0059 (5)0.0031 (5)0.0003 (5)
C130.0614 (9)0.0587 (9)0.0455 (8)0.0151 (7)0.0105 (7)0.0097 (7)
C140.0823 (11)0.0469 (8)0.0506 (8)0.0102 (8)0.0012 (8)0.0185 (7)
C150.0644 (9)0.0398 (7)0.0518 (8)0.0038 (6)0.0042 (7)0.0062 (6)
C160.0472 (7)0.0397 (7)0.0376 (6)0.0004 (5)0.0017 (5)0.0009 (5)
C210.0422 (6)0.0319 (6)0.0301 (5)0.0002 (5)0.0060 (5)0.0007 (4)
C220.0398 (7)0.0445 (7)0.0490 (7)0.0040 (5)0.0035 (5)0.0081 (6)
C230.0431 (7)0.0520 (8)0.0526 (8)0.0040 (6)0.0007 (6)0.0112 (6)
N240.0525 (7)0.0425 (6)0.0469 (6)0.0042 (5)0.0052 (5)0.0111 (5)
C250.0507 (7)0.0358 (6)0.0422 (7)0.0046 (5)0.0081 (6)0.0049 (5)
C260.0430 (7)0.0363 (6)0.0353 (6)0.0044 (5)0.0022 (5)0.0009 (5)
Geometric parameters (Å, º) top
F12—C121.3420 (15)C15—C161.3822 (18)
O1—C11.2149 (15)C15—H150.9300
C1—N11.3544 (16)C16—H160.9300
C1—C111.5008 (16)C21—C261.3872 (17)
N1—C211.3957 (15)C21—C221.3898 (17)
N1—H10.862 (18)C22—C231.3768 (19)
C11—C121.3855 (18)C22—H220.9300
C11—C161.3890 (18)C23—N241.3348 (18)
C12—C131.3786 (19)C23—H230.9300
C13—C141.373 (2)N24—C251.3327 (17)
C13—H130.9300C25—C261.3813 (17)
C14—C151.378 (2)C25—H250.9300
C14—H140.9300C26—H260.9300
O1—C1—N1123.86 (11)C16—C15—H15120.1
O1—C1—C11120.43 (11)C15—C16—C11120.97 (13)
N1—C1—C11115.65 (10)C15—C16—H16119.5
C1—N1—C21127.48 (11)C11—C16—H16119.5
C1—N1—H1118.5 (11)C26—C21—C22117.67 (11)
C21—N1—H1113.6 (11)C26—C21—N1124.33 (11)
C12—C11—C16117.35 (11)C22—C21—N1117.98 (11)
C12—C11—C1124.70 (11)C23—C22—C21119.04 (12)
C16—C11—C1117.91 (11)C23—C22—H22120.5
F12—C12—C13117.69 (12)C21—C22—H22120.5
F12—C12—C11119.85 (11)N24—C23—C22124.46 (13)
C13—C12—C11122.45 (13)N24—C23—H23117.8
C14—C13—C12118.78 (14)C22—C23—H23117.8
C14—C13—H13120.6C25—N24—C23115.37 (11)
C12—C13—H13120.6N24—C25—C26125.23 (12)
C13—C14—C15120.57 (13)N24—C25—H25117.4
C13—C14—H14119.7C26—C25—H25117.4
C15—C14—H14119.7C25—C26—C21118.22 (12)
C14—C15—C16119.85 (14)C25—C26—H26120.9
C14—C15—H15120.1C21—C26—H26120.9
O1—C1—N1—C215.8 (2)C14—C15—C16—C111.6 (2)
C11—C1—N1—C21176.87 (11)C12—C11—C16—C151.89 (18)
O1—C1—C11—C12148.22 (12)C1—C11—C16—C15179.81 (11)
N1—C1—C11—C1234.32 (16)C1—N1—C21—C2612.0 (2)
O1—C1—C11—C1629.53 (17)C1—N1—C21—C22169.47 (12)
N1—C1—C11—C16147.93 (11)C26—C21—C22—C230.84 (19)
C16—C11—C12—F12177.94 (10)N1—C21—C22—C23179.46 (12)
C1—C11—C12—F120.18 (18)C21—C22—C23—N240.8 (2)
C16—C11—C12—C130.80 (19)C22—C23—N24—C250.2 (2)
C1—C11—C12—C13178.56 (12)C23—N24—C25—C260.4 (2)
F12—C12—C13—C14179.38 (13)N24—C25—C26—C210.4 (2)
C11—C12—C13—C140.6 (2)C22—C21—C26—C250.28 (17)
C12—C13—C14—C151.0 (2)N1—C21—C26—C25178.81 (12)
C13—C14—C15—C160.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N24i0.862 (18)2.356 (18)3.0587 (16)138.9 (15)
N1—H1···F120.862 (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 top
Crystal data top
C12H9FN2OF(000) = 448
Mr = 216.21Dx = 1.447 Mg m3
Monoclinic, P21/nMelting point: 421 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 13.9411 (3) ÅCell parameters from 6156 reflections
b = 5.2040 (1) Åθ = 2.6–27.5°
c = 15.0752 (3) ŵ = 0.11 mm1
β = 114.812 (3)°T = 294 K
V = 992.74 (3) Å3Block, colourless
Z = 40.51 × 0.49 × 0.32 mm
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
2338 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.012
Graphite monochromatorθmax = 29.6°, θmin = 2.6°
ω scansh = 1918
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
k = 67
Tmin = 0.947, Tmax = 0.966l = 2020
8861 measured reflections9494 standard reflections every 60 min
2624 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0519P)2 + 0.3065P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2624 reflectionsΔρmax = 0.25 e Å3
150 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.012 (3)
Crystal data top
C12H9FN2OV = 992.74 (3) Å3
Mr = 216.21Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.9411 (3) ŵ = 0.11 mm1
b = 5.2040 (1) ÅT = 294 K
c = 15.0752 (3) Å0.51 × 0.49 × 0.32 mm
β = 114.812 (3)°
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
2338 reflections with I > 2σ(I)
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
Rint = 0.012
Tmin = 0.947, Tmax = 0.9669494 standard reflections every 60 min
8861 measured reflections intensity decay: 1%
2624 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.25 e Å3
2624 reflectionsΔρmin = 0.19 e Å3
150 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
F140.90021 (7)0.1346 (2)0.04677 (7)0.0661 (3)
O10.61595 (9)0.33340 (17)0.14280 (9)0.0553 (3)
C10.63029 (9)0.1073 (2)0.12902 (8)0.0334 (2)
N10.58246 (8)0.08878 (19)0.15340 (7)0.0338 (2)
H10.5976 (12)0.243 (3)0.1431 (11)0.044 (4)*
C110.70251 (8)0.0311 (2)0.08326 (8)0.0308 (2)
C120.78845 (9)0.1890 (2)0.09844 (9)0.0364 (3)
H120.80020.33410.13760.044*
C130.85672 (10)0.1329 (3)0.05593 (10)0.0427 (3)
H130.91520.23600.06710.051*
C140.83564 (10)0.0796 (3)0.00319 (9)0.0399 (3)
C150.75105 (10)0.2392 (2)0.02129 (9)0.0387 (3)
H150.73880.38090.06220.046*
C160.68448 (9)0.1830 (2)0.02329 (9)0.0362 (3)
H160.62720.28950.01300.043*
C210.50573 (8)0.0640 (2)0.19131 (8)0.0300 (2)
C220.42809 (10)0.2510 (2)0.16657 (9)0.0374 (3)
H220.42960.38360.12580.045*
N230.35152 (9)0.2531 (2)0.19733 (9)0.0446 (3)
C240.35111 (11)0.0602 (3)0.25561 (10)0.0440 (3)
H240.29770.05560.27720.053*
C250.42583 (11)0.1324 (3)0.28530 (9)0.0425 (3)
H250.42270.26190.32650.051*
C260.50551 (10)0.1321 (2)0.25341 (9)0.0369 (3)
H260.55720.25920.27300.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F140.0582 (5)0.0835 (7)0.0797 (6)0.0152 (5)0.0514 (5)0.0249 (5)
O10.0769 (7)0.0246 (4)0.0917 (8)0.0005 (4)0.0621 (6)0.0012 (5)
C10.0372 (5)0.0267 (5)0.0407 (6)0.0001 (4)0.0208 (5)0.0003 (4)
N10.0399 (5)0.0240 (4)0.0467 (5)0.0006 (4)0.0273 (4)0.0011 (4)
C110.0333 (5)0.0279 (5)0.0340 (5)0.0005 (4)0.0169 (4)0.0023 (4)
C120.0362 (6)0.0342 (6)0.0394 (6)0.0063 (4)0.0167 (5)0.0049 (5)
C130.0345 (6)0.0466 (7)0.0500 (7)0.0111 (5)0.0207 (5)0.0053 (6)
C140.0369 (6)0.0483 (7)0.0418 (6)0.0005 (5)0.0238 (5)0.0013 (5)
C150.0458 (6)0.0352 (6)0.0412 (6)0.0041 (5)0.0241 (5)0.0055 (5)
C160.0394 (6)0.0316 (6)0.0433 (6)0.0075 (4)0.0230 (5)0.0031 (5)
C210.0330 (5)0.0267 (5)0.0341 (5)0.0036 (4)0.0178 (4)0.0038 (4)
C220.0421 (6)0.0299 (5)0.0468 (6)0.0020 (5)0.0252 (5)0.0029 (5)
N230.0440 (6)0.0397 (6)0.0604 (7)0.0026 (5)0.0321 (5)0.0020 (5)
C240.0466 (7)0.0446 (7)0.0534 (7)0.0092 (5)0.0333 (6)0.0092 (6)
C250.0543 (7)0.0378 (6)0.0443 (6)0.0088 (5)0.0295 (6)0.0007 (5)
C260.0421 (6)0.0322 (6)0.0393 (6)0.0001 (5)0.0199 (5)0.0028 (4)
Geometric parameters (Å, º) top
F14—C141.3490 (13)C15—C161.3864 (16)
O1—C11.2259 (14)C15—H150.9300
C1—N11.3514 (14)C16—H160.9300
C1—C111.4933 (15)C21—C221.3848 (16)
N1—C211.4144 (13)C21—C261.3859 (16)
N1—H10.859 (17)C22—N231.3305 (15)
C11—C161.3894 (16)C22—H220.9300
C11—C121.3904 (15)N23—C241.3358 (18)
C12—C131.3835 (17)C24—C251.378 (2)
C12—H120.9300C24—H240.9300
C13—C141.3725 (19)C25—C261.3833 (16)
C13—H130.9300C25—H250.9300
C14—C151.3729 (17)C26—H260.9300
O1—C1—N1122.98 (11)C16—C15—H15121.0
O1—C1—C11121.51 (10)C15—C16—C11120.63 (10)
N1—C1—C11115.50 (10)C15—C16—H16119.7
C1—N1—C21125.76 (10)C11—C16—H16119.7
C1—N1—H1117.9 (10)C22—C21—C26118.45 (10)
C21—N1—H1116.3 (10)C22—C21—N1117.73 (10)
C16—C11—C12119.29 (10)C26—C21—N1123.80 (10)
C16—C11—C1122.72 (10)N23—C22—C21124.25 (11)
C12—C11—C1117.93 (10)N23—C22—H22117.9
C13—C12—C11120.76 (11)C21—C22—H22117.9
C13—C12—H12119.6C22—N23—C24116.64 (11)
C11—C12—H12119.6N23—C24—C25123.31 (11)
C14—C13—C12118.01 (11)N23—C24—H24118.3
C14—C13—H13121.0C25—C24—H24118.3
C12—C13—H13121.0C24—C25—C26119.61 (11)
F14—C14—C13118.83 (11)C24—C25—H25120.2
F14—C14—C15117.91 (12)C26—C25—H25120.2
C13—C14—C15123.26 (11)C25—C26—C21117.73 (11)
C14—C15—C16118.03 (11)C25—C26—H26121.1
C14—C15—H15121.0C21—C26—H26121.1
O1—C1—N1—C214.3 (2)C14—C15—C16—C110.93 (19)
C11—C1—N1—C21175.46 (10)C12—C11—C16—C150.12 (18)
O1—C1—C11—C16146.70 (13)C1—C11—C16—C15176.93 (11)
N1—C1—C11—C1633.10 (16)C1—N1—C21—C22147.25 (12)
O1—C1—C11—C1230.39 (17)C1—N1—C21—C2634.42 (18)
N1—C1—C11—C12149.82 (11)C26—C21—C22—N231.13 (18)
C16—C11—C12—C131.08 (18)N1—C21—C22—N23179.55 (11)
C1—C11—C12—C13178.27 (11)C21—C22—N23—C240.13 (19)
C11—C12—C13—C141.42 (19)C22—N23—C24—C251.1 (2)
C12—C13—C14—F14178.74 (12)N23—C24—C25—C260.7 (2)
C12—C13—C14—C150.6 (2)C24—C25—C26—C210.61 (18)
F14—C14—C15—C16179.91 (11)C22—C21—C26—C251.45 (17)
C13—C14—C15—C160.6 (2)N1—C21—C26—C25179.76 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.859 (17)2.221 (17)3.0575 (13)164.6 (14)
C26—H26···O10.932.452.8987 (15)109
Symmetry code: (i) x, y+1, z.
(Fpm_N-10-121) 4-Fluoro-N-(pyridin-3-yl)benzamide top
Crystal data top
C12H9FN2OF(000) = 448
Mr = 216.21Dx = 1.422 Mg m3
Monoclinic, P21/nMelting point: 423 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 3.9077 (2) ÅCell parameters from 1505 reflections
b = 24.2444 (12) Åθ = 2.6–27.5°
c = 10.7012 (5) ŵ = 0.11 mm1
β = 95.181 (5)°T = 294 K
V = 1009.69 (9) Å3Block, colourless
Z = 40.24 × 0.05 × 0.03 mm
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
1154 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.049
Graphite monochromatorθmax = 27.4°, θmin = 2.1°
ω scansh = 54
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
k = 3131
Tmin = 0.975, Tmax = 0.997l = 1313
6537 measured reflections6646 standard reflections every 60 min
2162 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 0.96 w = 1/[σ2(Fo2) + (0.027P)2]
where P = (Fo2 + 2Fc2)/3
2162 reflections(Δ/σ)max < 0.001
149 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C12H9FN2OV = 1009.69 (9) Å3
Mr = 216.21Z = 4
Monoclinic, P21/nMo Kα radiation
a = 3.9077 (2) ŵ = 0.11 mm1
b = 24.2444 (12) ÅT = 294 K
c = 10.7012 (5) Å0.24 × 0.05 × 0.03 mm
β = 95.181 (5)°
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
1154 reflections with I > 2σ(I)
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
Rint = 0.049
Tmin = 0.975, Tmax = 0.9976646 standard reflections every 60 min
6537 measured reflections intensity decay: 1%
2162 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 0.96Δρmax = 0.16 e Å3
2162 reflectionsΔρmin = 0.16 e Å3
149 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
F140.2906 (5)0.04664 (7)0.14409 (16)0.0977 (6)
O10.9086 (5)0.13840 (8)0.50443 (16)0.0803 (6)
C10.8398 (6)0.14048 (10)0.3905 (2)0.0510 (6)
N10.9083 (5)0.18577 (8)0.3220 (2)0.0489 (5)
H10.856 (6)0.1854 (10)0.244 (3)0.065 (8)*
C110.6861 (6)0.09229 (9)0.3203 (2)0.0459 (6)
C120.7182 (7)0.04148 (10)0.3780 (2)0.0608 (7)
H120.82840.03910.45860.073*
C130.5919 (7)0.00553 (11)0.3198 (3)0.0703 (8)
H130.62020.03970.35880.084*
C140.4227 (7)0.00075 (11)0.2025 (3)0.0637 (7)
C150.3809 (6)0.04843 (11)0.1424 (2)0.0584 (7)
H150.26530.05050.06260.070*
C160.5127 (6)0.09519 (10)0.2015 (2)0.0500 (6)
H160.48520.12910.16140.060*
C211.0631 (5)0.23532 (9)0.3654 (2)0.0437 (6)
C221.1297 (6)0.24915 (10)0.4914 (2)0.0531 (6)
H221.07210.22390.55160.064*
N231.2724 (6)0.29689 (8)0.52998 (18)0.0595 (6)
C241.3530 (7)0.33274 (10)0.4437 (2)0.0602 (7)
H241.44900.36630.47020.072*
C251.3012 (6)0.32256 (10)0.3172 (2)0.0555 (7)
H251.36450.34840.25930.067*
C261.1541 (6)0.27355 (10)0.2784 (2)0.0510 (6)
H261.11510.26590.19310.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F140.1541 (16)0.0589 (10)0.0775 (13)0.0296 (11)0.0042 (11)0.0125 (9)
O10.1340 (17)0.0709 (13)0.0328 (11)0.0207 (12)0.0111 (10)0.0053 (9)
C10.0675 (16)0.0503 (15)0.0344 (14)0.0018 (13)0.0004 (12)0.0020 (11)
N10.0713 (14)0.0467 (12)0.0275 (11)0.0011 (11)0.0029 (10)0.0017 (9)
C110.0587 (14)0.0442 (13)0.0345 (13)0.0005 (12)0.0027 (11)0.0031 (11)
C120.0855 (19)0.0517 (16)0.0432 (15)0.0023 (14)0.0055 (13)0.0081 (12)
C130.103 (2)0.0483 (17)0.0588 (19)0.0003 (15)0.0020 (16)0.0083 (14)
C140.092 (2)0.0485 (16)0.0510 (17)0.0129 (14)0.0058 (15)0.0081 (13)
C150.0762 (17)0.0557 (16)0.0420 (15)0.0072 (14)0.0028 (12)0.0030 (12)
C160.0642 (15)0.0451 (14)0.0399 (14)0.0009 (12)0.0005 (11)0.0054 (11)
C210.0548 (14)0.0445 (13)0.0308 (12)0.0053 (11)0.0012 (10)0.0023 (10)
C220.0798 (18)0.0513 (15)0.0272 (12)0.0012 (13)0.0004 (11)0.0003 (11)
N230.0942 (16)0.0471 (12)0.0346 (12)0.0008 (12)0.0077 (11)0.0055 (10)
C240.0870 (19)0.0464 (14)0.0438 (16)0.0001 (14)0.0123 (13)0.0041 (12)
C250.0794 (17)0.0476 (15)0.0380 (14)0.0046 (13)0.0035 (12)0.0014 (11)
C260.0712 (16)0.0511 (15)0.0293 (13)0.0018 (13)0.0029 (11)0.0002 (11)
Geometric parameters (Å, º) top
F14—C141.355 (3)C15—C161.375 (3)
O1—C11.225 (3)C15—H150.9300
C1—N11.360 (3)C16—H160.9300
C1—C111.486 (3)C21—C261.383 (3)
N1—C211.405 (3)C21—C221.391 (3)
N1—H10.84 (3)C22—N231.334 (3)
C11—C121.379 (3)C22—H220.9300
C11—C161.387 (3)N23—C241.326 (3)
C12—C131.369 (3)C24—C251.373 (3)
C12—H120.9300C24—H240.9300
C13—C141.369 (4)C25—C261.368 (3)
C13—H130.9300C25—H250.9300
C14—C151.358 (3)C26—H260.9300
O1—C1—N1122.2 (2)C16—C15—H15120.6
O1—C1—C11120.9 (2)C15—C16—C11120.8 (2)
N1—C1—C11116.9 (2)C15—C16—H16119.6
C1—N1—C21127.7 (2)C11—C16—H16119.6
C1—N1—H1118.9 (18)C26—C21—C22117.0 (2)
C21—N1—H1113.4 (18)C26—C21—N1118.6 (2)
C12—C11—C16118.2 (2)C22—C21—N1124.3 (2)
C12—C11—C1117.4 (2)N23—C22—C21123.0 (2)
C16—C11—C1124.4 (2)N23—C22—H22118.5
C13—C12—C11121.7 (2)C21—C22—H22118.5
C13—C12—H12119.2C24—N23—C22118.2 (2)
C11—C12—H12119.2N23—C24—C25123.0 (2)
C12—C13—C14118.1 (2)N23—C24—H24118.5
C12—C13—H13121.0C25—C24—H24118.5
C14—C13—H13121.0C26—C25—C24118.4 (2)
F14—C14—C15118.5 (2)C26—C25—H25120.8
F14—C14—C13119.1 (2)C24—C25—H25120.8
C15—C14—C13122.4 (2)C25—C26—C21120.3 (2)
C14—C15—C16118.8 (2)C25—C26—H26119.9
C14—C15—H15120.6C21—C26—H26119.9
O1—C1—N1—C210.6 (4)C14—C15—C16—C110.2 (4)
C11—C1—N1—C21177.6 (2)C12—C11—C16—C150.9 (3)
O1—C1—C11—C1218.9 (3)C1—C11—C16—C15179.3 (2)
N1—C1—C11—C12159.2 (2)C1—N1—C21—C26171.0 (2)
O1—C1—C11—C16160.8 (2)C1—N1—C21—C229.6 (4)
N1—C1—C11—C1621.0 (3)C26—C21—C22—N230.4 (3)
C16—C11—C12—C131.7 (4)N1—C21—C22—N23179.0 (2)
C1—C11—C12—C13178.5 (2)C21—C22—N23—C240.2 (4)
C11—C12—C13—C141.7 (4)C22—N23—C24—C251.0 (4)
C12—C13—C14—F14178.9 (2)N23—C24—C25—C261.2 (4)
C12—C13—C14—C150.9 (4)C24—C25—C26—C210.5 (4)
F14—C14—C15—C16179.6 (2)C22—C21—C26—C250.3 (3)
C13—C14—C15—C160.2 (4)N1—C21—C26—C25179.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N23i0.84 (3)2.32 (3)3.151 (3)167 (2)
C22—H22···O10.932.212.828 (3)123
C16—H16···N23i0.932.603.404 (3)146
C26—H26···N23i0.932.603.390 (3)144
Symmetry code: (i) x1/2, y+1/2, z1/2.
(Fmm-10-122) 3-Fluoro-N-(pyridin-3-yl)benzamide top
Crystal data top
C12H9FN2ODx = 1.408 Mg m3
Mr = 216.21Melting point: 424 K
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 3744 reflections
a = 11.3020 (3) Åθ = 2.6–27.5°
b = 11.8371 (3) ŵ = 0.11 mm1
c = 7.6218 (2) ÅT = 294 K
V = 1019.67 (5) Å3Block, colourless
Z = 40.38 × 0.10 × 0.08 mm
F(000) = 448
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
981 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.021
Graphite monochromatorθmax = 27.8°, θmin = 2.5°
ω scansh = 1414
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
k = 1414
Tmin = 0.961, Tmax = 0.992l = 99
7366 measured reflections7839 standard reflections every 60 min
1239 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0521P)2]
where P = (Fo2 + 2Fc2)/3
1239 reflections(Δ/σ)max < 0.001
149 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.15 e Å3
Crystal data top
C12H9FN2OV = 1019.67 (5) Å3
Mr = 216.21Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 11.3020 (3) ŵ = 0.11 mm1
b = 11.8371 (3) ÅT = 294 K
c = 7.6218 (2) Å0.38 × 0.10 × 0.08 mm
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
981 reflections with I > 2σ(I)
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
Rint = 0.021
Tmin = 0.961, Tmax = 0.9927839 standard reflections every 60 min
7366 measured reflections intensity decay: 1%
1239 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0331 restraint
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.15 e Å3
1239 reflectionsΔρmin = 0.15 e Å3
149 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
F130.30425 (15)0.12223 (10)0.3223 (3)0.0941 (6)
O10.11724 (13)0.26118 (12)0.3503 (3)0.0625 (5)
C10.22288 (17)0.27534 (15)0.3293 (3)0.0426 (5)
N10.27110 (16)0.37272 (14)0.2715 (3)0.0436 (4)
H10.338 (3)0.380 (2)0.254 (4)0.066 (8)*
C110.30815 (16)0.18037 (16)0.3624 (3)0.0427 (5)
C120.2688 (2)0.07197 (14)0.3258 (3)0.0497 (5)
H120.19400.05990.27880.060*
C130.3428 (2)0.01694 (18)0.3605 (4)0.0583 (6)
C140.4525 (2)0.0041 (2)0.4304 (4)0.0669 (7)
H140.50030.06640.45320.080*
C150.4906 (2)0.1030 (2)0.4663 (4)0.0672 (7)
H150.56560.11390.51360.081*
C160.4191 (2)0.19556 (18)0.4331 (3)0.0521 (6)
H160.44600.26800.45860.063*
C210.21051 (16)0.47223 (16)0.2236 (3)0.0389 (4)
C220.09061 (18)0.49007 (18)0.2513 (3)0.0485 (6)
H220.04640.43330.30450.058*
N230.03598 (16)0.58587 (15)0.2043 (3)0.0568 (5)
C240.09922 (19)0.66611 (18)0.1271 (4)0.0549 (6)
H240.06130.73230.09310.066*
C250.21805 (18)0.65550 (18)0.0953 (3)0.0509 (6)
H250.25990.71360.04150.061*
C260.27408 (18)0.55768 (15)0.1443 (3)0.0460 (5)
H260.35470.54890.12400.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F130.1067 (13)0.0402 (7)0.1355 (17)0.0016 (7)0.0159 (13)0.0029 (10)
O10.0375 (8)0.0469 (8)0.1031 (15)0.0019 (6)0.0128 (8)0.0056 (10)
C10.0389 (11)0.0397 (10)0.0492 (12)0.0001 (8)0.0030 (10)0.0049 (10)
N10.0300 (9)0.0397 (8)0.0612 (11)0.0025 (7)0.0042 (9)0.0016 (7)
C110.0413 (10)0.0406 (10)0.0462 (12)0.0004 (8)0.0040 (9)0.0015 (9)
C120.0490 (12)0.0426 (11)0.0574 (13)0.0015 (9)0.0031 (11)0.0010 (11)
C130.0638 (15)0.0373 (11)0.0738 (18)0.0002 (10)0.0162 (13)0.0041 (12)
C140.0595 (15)0.0529 (13)0.0883 (19)0.0138 (12)0.0138 (14)0.0233 (13)
C150.0491 (13)0.0698 (17)0.0826 (18)0.0040 (12)0.0063 (13)0.0229 (13)
C160.0478 (12)0.0451 (12)0.0635 (14)0.0027 (10)0.0030 (11)0.0063 (11)
C210.0351 (10)0.0361 (10)0.0456 (11)0.0002 (8)0.0001 (9)0.0049 (8)
C220.0362 (10)0.0417 (11)0.0677 (15)0.0011 (8)0.0020 (10)0.0012 (10)
N230.0400 (10)0.0450 (9)0.0853 (15)0.0056 (8)0.0006 (10)0.0031 (10)
C240.0517 (14)0.0385 (11)0.0745 (17)0.0040 (9)0.0047 (12)0.0028 (11)
C250.0496 (14)0.0414 (10)0.0616 (14)0.0048 (9)0.0053 (11)0.0048 (10)
C260.0358 (11)0.0467 (11)0.0555 (12)0.0005 (8)0.0035 (10)0.0023 (10)
Geometric parameters (Å, º) top
F13—C131.352 (3)C15—C161.385 (3)
O1—C11.216 (2)C15—H150.9300
C1—N11.349 (2)C16—H160.9300
C1—C111.502 (3)C21—C261.380 (3)
N1—C211.411 (2)C21—C221.388 (2)
N1—H10.77 (3)C22—N231.340 (3)
C11—C161.376 (3)C22—H220.9300
C11—C121.386 (3)N23—C241.326 (3)
C12—C131.369 (3)C24—C251.370 (3)
C12—H120.9300C24—H240.9300
C13—C141.359 (4)C25—C261.372 (3)
C14—C151.367 (4)C25—H250.9300
C14—H140.9300C26—H260.9300
O1—C1—N1123.87 (18)C16—C15—H15119.6
O1—C1—C11120.31 (17)C11—C16—C15120.0 (2)
N1—C1—C11115.79 (17)C11—C16—H16120.0
C1—N1—C21127.01 (17)C15—C16—H16120.0
C1—N1—H1123.1 (19)C26—C21—C22117.60 (18)
C21—N1—H1109.8 (19)C26—C21—N1118.21 (16)
C16—C11—C12119.44 (19)C22—C21—N1124.19 (18)
C16—C11—C1123.53 (18)N23—C22—C21122.56 (19)
C12—C11—C1116.96 (17)N23—C22—H22118.7
C13—C12—C11118.5 (2)C21—C22—H22118.7
C13—C12—H12120.8C24—N23—C22118.44 (18)
C11—C12—H12120.8N23—C24—C25122.7 (2)
F13—C13—C14118.8 (2)N23—C24—H24118.6
F13—C13—C12118.1 (2)C25—C24—H24118.6
C14—C13—C12123.2 (2)C24—C25—C26118.80 (19)
C13—C14—C15118.0 (2)C24—C25—H25120.6
C13—C14—H14121.0C26—C25—H25120.6
C15—C14—H14121.0C25—C26—C21119.85 (19)
C14—C15—C16120.9 (2)C25—C26—H26120.1
C14—C15—H15119.6C21—C26—H26120.1
O1—C1—N1—C211.0 (4)C12—C11—C16—C150.3 (4)
C11—C1—N1—C21177.0 (2)C1—C11—C16—C15177.3 (2)
O1—C1—C11—C16143.9 (2)C14—C15—C16—C110.3 (4)
N1—C1—C11—C1637.9 (3)C1—N1—C21—C26171.0 (2)
O1—C1—C11—C1233.1 (3)C1—N1—C21—C229.1 (3)
N1—C1—C11—C12145.0 (2)C26—C21—C22—N230.1 (3)
C16—C11—C12—C130.5 (3)N1—C21—C22—N23179.9 (2)
C1—C11—C12—C13177.6 (2)C21—C22—N23—C240.6 (4)
C11—C12—C13—F13179.2 (2)C22—N23—C24—C250.7 (4)
C11—C12—C13—C140.5 (4)N23—C24—C25—C260.4 (4)
F13—C13—C14—C15179.2 (3)C24—C25—C26—C210.1 (4)
C12—C13—C14—C150.5 (4)C22—C21—C26—C250.3 (3)
C13—C14—C15—C160.3 (4)N1—C21—C26—C25179.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N23i0.77 (3)2.31 (3)3.077 (3)176 (3)
C22—H22···O10.932.222.829 (3)123
Symmetry code: (i) x+1/2, y+1, z.
(Fom_O-11-009) 2-Fluoro-N-(pyridin-3-yl)benzamide top
Crystal data top
C12H9FN2OF(000) = 1344
Mr = 216.21Dx = 1.436 Mg m3
Monoclinic, P21Melting point: 363 K
Hall symbol: P 2ybCu Kα radiation, λ = 1.54184 Å
a = 16.2051 (4) ÅCell parameters from 6501 reflections
b = 5.2239 (1) Åθ = 2.6–27.5°
c = 35.8162 (9) ŵ = 0.89 mm1
β = 98.405 (3)°T = 294 K
V = 2999.41 (12) Å3Needle, colourless
Z = 120.47 × 0.23 × 0.16 mm
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
5064 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 58.3°, θmin = 2.8°
ω scansh = 1717
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
k = 55
Tmin = 0.679, Tmax = 0.870l = 3839
13035 measured reflections13041 standard reflections every 60 min
5835 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.059 w = 1/[σ2(Fo2) + (0.099P)2 + 1.37P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.176(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.16 e Å3
5835 reflectionsΔρmin = 0.19 e Å3
1315 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
638 restraintsExtinction coefficient: 0.00067 (16)
Primary atom site location: structure-invariant direct methodsAbsolute structure: (Flack, 1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.0 (13)
Crystal data top
C12H9FN2OV = 2999.41 (12) Å3
Mr = 216.21Z = 12
Monoclinic, P21Cu Kα radiation
a = 16.2051 (4) ŵ = 0.89 mm1
b = 5.2239 (1) ÅT = 294 K
c = 35.8162 (9) Å0.47 × 0.23 × 0.16 mm
β = 98.405 (3)°
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
5064 reflections with I > 2σ(I)
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
Rint = 0.026
Tmin = 0.679, Tmax = 0.870θmax = 58.3°
13035 measured reflections13041 standard reflections every 60 min
5835 independent reflections intensity decay: 1%
Refinement top
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.176Δρmax = 0.16 e Å3
S = 1.06Δρmin = 0.19 e Å3
5835 reflectionsAbsolute structure: (Flack, 1983)
1315 parametersAbsolute structure parameter: 0.0 (13)
638 restraints
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
F12A0.61665 (18)0.3940 (9)0.20484 (7)0.0654 (10)0.87
O1A0.7374 (5)0.2255 (11)0.16994 (17)0.0611 (16)0.87
C1A0.7222 (4)0.0019 (13)0.17923 (17)0.0513 (15)0.87
N1A0.7126 (3)0.1906 (10)0.15429 (10)0.0486 (12)0.87
H1A0.70820.34070.16360.058*0.87
C11A0.7143 (3)0.0694 (13)0.22009 (12)0.0440 (13)0.87
C12A0.6643 (3)0.2531 (11)0.23194 (12)0.0457 (13)0.87
C13A0.6566 (3)0.3054 (15)0.26833 (15)0.0577 (15)0.87
H13A0.62170.43420.27480.069*0.87
C14A0.7057 (5)0.1494 (16)0.29625 (15)0.072 (2)0.87
H14A0.70510.18070.32180.086*0.87
C15A0.7523 (5)0.0408 (19)0.28560 (19)0.072 (2)0.87
H15A0.78280.14090.30420.086*0.87
C16A0.7574 (4)0.0961 (14)0.24792 (17)0.0545 (15)0.87
H16A0.78780.23560.24120.065*0.87
C21A0.7089 (3)0.1803 (11)0.11538 (12)0.0359 (11)0.87
C22A0.6681 (3)0.3736 (14)0.09502 (16)0.0570 (16)0.87
H22A0.64470.50160.10810.068*0.87
N23A0.6592 (3)0.3929 (11)0.05655 (11)0.0564 (12)0.87
C24A0.6953 (5)0.2069 (16)0.03895 (17)0.0650 (19)0.87
H24A0.69140.21480.01280.078*0.87
C25A0.7388 (5)0.0004 (15)0.05770 (18)0.058 (2)0.87
H25A0.76230.12560.04420.070*0.87
C26A0.7458 (3)0.0117 (12)0.09557 (15)0.0465 (13)0.87
H26A0.77480.14590.10860.056*0.87
F12B0.11662 (19)0.3096 (9)0.13382 (7)0.0630 (10)0.83
O1B0.2384 (7)0.9343 (15)0.1828 (3)0.060 (2)0.83
C1B0.2210 (5)0.7171 (12)0.17087 (17)0.0401 (14)0.83
N1B0.2154 (3)0.5166 (9)0.19422 (10)0.0427 (11)0.83
H1B0.20980.36720.18410.051*0.83
C11B0.2096 (3)0.6627 (11)0.12957 (12)0.0383 (11)0.83
C12B0.1568 (3)0.4647 (13)0.11208 (14)0.0487 (14)0.83
C13B0.1456 (3)0.4249 (14)0.07383 (13)0.0535 (15)0.83
H13B0.11240.29070.06330.064*0.83
C14B0.1838 (4)0.5850 (14)0.05137 (14)0.0522 (15)0.83
H14B0.17740.55690.02550.063*0.83
C15B0.2313 (4)0.7856 (18)0.06667 (15)0.0648 (19)0.83
H15B0.25440.89900.05110.078*0.83
C16B0.2450 (3)0.8200 (14)0.10576 (14)0.0482 (14)0.83
H16B0.27910.95340.11590.058*0.83
C21B0.2179 (3)0.5298 (13)0.23371 (13)0.0458 (14)0.83
C22B0.1794 (3)0.3266 (12)0.24978 (14)0.0467 (14)0.83
H22B0.15530.19700.23400.056*0.83
N23B0.1754 (3)0.3093 (13)0.28691 (12)0.0594 (14)0.83
C24B0.2110 (5)0.4786 (15)0.30811 (18)0.0564 (17)0.83
H24B0.20920.46520.33390.068*0.83
C25B0.2543 (5)0.6919 (18)0.29504 (18)0.062 (2)0.83
H25B0.27880.81670.31160.075*0.83
C26B0.2579 (4)0.7040 (14)0.25738 (15)0.0471 (14)0.83
H26B0.28830.83380.24790.056*0.83
F12C1.0459 (2)0.9066 (9)0.20364 (7)0.0662 (10)0.83
O1C0.9227 (4)0.2770 (11)0.15497 (15)0.0536 (13)0.83
C1C0.9415 (4)0.4960 (14)0.16617 (16)0.0493 (16)0.83
N1C0.9465 (3)0.7003 (10)0.14310 (11)0.0468 (11)0.83
H1C0.95130.84840.15370.056*0.83
C11C0.9544 (4)0.5719 (19)0.20840 (15)0.053 (2)0.83
C12C1.0002 (5)0.760 (2)0.2247 (2)0.064 (3)0.83
C13C1.0161 (7)0.815 (2)0.2640 (3)0.089 (5)0.83
H13C1.04760.95520.27360.107*0.83
C14C0.9821 (7)0.649 (2)0.2863 (2)0.072 (3)0.83
H14C0.99210.66970.31230.087*0.83
C15C0.9322 (6)0.445 (2)0.2708 (2)0.062 (3)0.83
H15C0.90760.33680.28660.075*0.83
C16C0.9192 (6)0.405 (2)0.2329 (2)0.064 (3)0.83
H16C0.88700.26710.22310.077*0.83
C21C0.9447 (4)0.6945 (14)0.10344 (14)0.0414 (16)0.83
C22C0.9853 (3)0.8832 (14)0.08752 (14)0.0509 (15)0.83
H22C1.01221.00750.10350.061*0.83
N23C0.9896 (3)0.9043 (12)0.05095 (13)0.0548 (13)0.83
C24C0.9524 (7)0.702 (3)0.02853 (17)0.072 (4)0.83
H24C0.95540.70350.00280.086*0.83
C25C0.9145 (5)0.513 (2)0.0421 (2)0.057 (3)0.83
H25C0.88980.38840.02570.068*0.83
C26C0.9090 (5)0.490 (2)0.0810 (2)0.063 (3)0.83
H26C0.88380.35100.09090.076*0.83
F12D0.54501 (19)0.1874 (9)0.12603 (7)0.0703 (11)0.87
O1D0.4286 (6)0.4349 (14)0.1593 (3)0.069 (2)0.87
C1D0.4419 (4)0.2167 (12)0.15033 (16)0.0440 (13)0.87
N1D0.4494 (3)0.0152 (10)0.17516 (11)0.0467 (11)0.87
H1D0.45330.13570.16600.056*0.87
C11D0.4483 (3)0.1584 (12)0.11076 (13)0.0440 (13)0.87
C12D0.4979 (3)0.0417 (14)0.09936 (15)0.0527 (15)0.87
C13D0.5013 (3)0.0914 (15)0.06184 (15)0.0570 (15)0.87
H13D0.53500.22370.05550.068*0.87
C14D0.4590 (5)0.0404 (17)0.03548 (17)0.068 (2)0.87
H14D0.46340.00540.01040.081*0.87
C15D0.4056 (6)0.240 (2)0.0445 (2)0.077 (3)0.87
H15D0.37440.33520.02560.092*0.87
C16D0.4012 (5)0.2878 (18)0.08191 (18)0.068 (2)0.87
H16D0.36460.41350.08790.081*0.87
C21D0.4510 (3)0.0352 (14)0.21442 (13)0.0510 (15)0.87
C22D0.4937 (3)0.1670 (12)0.23574 (13)0.0503 (14)0.87
H22D0.51780.29470.22280.060*0.87
N23D0.5012 (3)0.1837 (13)0.27274 (12)0.0655 (14)0.87
C24D0.4674 (3)0.0048 (14)0.29047 (14)0.0545 (15)0.87
H24D0.47400.00110.31670.065*0.87
C25D0.4251 (4)0.1965 (15)0.27300 (14)0.0581 (17)0.87
H25D0.40150.31870.28710.070*0.87
C26D0.4151 (3)0.2197 (14)0.23314 (13)0.0487 (14)0.87
H26D0.38540.35420.22060.058*0.87
F12E0.7145 (3)0.8784 (14)0.45631 (12)0.0638 (16)0.50
O1E0.588 (3)0.257 (4)0.4885 (12)0.059 (7)0.50
C1E0.6071 (11)0.475 (3)0.4806 (3)0.049 (3)0.50
N1E0.6165 (5)0.6706 (19)0.50600 (17)0.050 (2)0.50
H1E0.62120.82140.49690.060*0.50
C11E0.6168 (12)0.568 (3)0.4407 (4)0.045 (4)0.50
C12E0.6647 (9)0.741 (3)0.4305 (3)0.044 (3)0.50
C13E0.6729 (16)0.810 (5)0.3930 (6)0.072 (5)0.50
H13E0.70820.94300.38830.086*0.50
C14E0.6274 (18)0.677 (7)0.3635 (7)0.061 (6)0.50
H14E0.62740.72680.33850.073*0.50
C15E0.584 (2)0.475 (9)0.3720 (11)0.059 (6)0.50
H15E0.55480.37380.35310.071*0.50
C16E0.5823 (11)0.415 (5)0.4111 (7)0.046 (4)0.50
H16E0.55630.26420.41680.055*0.50
C21E0.6195 (9)0.655 (2)0.5451 (3)0.034 (3)0.50
C22E0.6612 (8)0.843 (3)0.5657 (3)0.047 (3)0.50
H22E0.68630.96800.55280.056*0.50
N23E0.6697 (8)0.863 (2)0.6044 (3)0.051 (3)0.50
C24E0.6376 (17)0.681 (4)0.6229 (6)0.054 (5)0.50
H24E0.64550.68180.64910.064*0.50
C25E0.588 (2)0.475 (7)0.6018 (12)0.052 (6)0.50
H25E0.55860.36540.61520.062*0.50
C26E0.5846 (17)0.440 (4)0.5677 (6)0.055 (5)0.50
H26E0.56180.29090.55620.066*0.50
F12G0.7150 (4)0.8899 (17)0.53393 (14)0.0807 (19)0.50
O1G0.604 (3)0.249 (4)0.4877 (13)0.064 (7)0.50
C1G0.6125 (11)0.474 (3)0.4973 (4)0.054 (4)0.50
N1G0.6164 (6)0.676 (2)0.4738 (2)0.065 (2)0.50
H1G0.62330.82440.48410.078*0.50
C11G0.6300 (9)0.544 (3)0.5385 (4)0.057 (4)0.50
C12G0.6729 (9)0.733 (3)0.5549 (3)0.045 (3)0.50
C13G0.6883 (9)0.794 (3)0.5930 (4)0.057 (3)0.50
H13G0.72170.92950.60310.069*0.50
C14G0.6459 (18)0.621 (5)0.6147 (5)0.060 (5)0.50
H14G0.64860.65300.64040.072*0.50
C15G0.605 (2)0.426 (7)0.6013 (11)0.051 (6)0.50
H15G0.58400.30400.61630.061*0.50
C16G0.5935 (16)0.412 (6)0.5596 (6)0.070 (7)0.50
H16G0.55530.29300.54830.084*0.50
C21G0.6102 (14)0.665 (3)0.4340 (4)0.051 (4)0.50
C22G0.6538 (9)0.845 (3)0.4177 (4)0.063 (4)0.50
H22G0.68610.95670.43400.076*0.50
N23G0.6555 (13)0.877 (3)0.3815 (4)0.073 (5)0.50
C24G0.6058 (19)0.661 (7)0.3602 (9)0.071 (7)0.50
H24G0.60600.65010.33430.085*0.50
C25G0.564 (2)0.493 (10)0.3755 (12)0.068 (8)0.50
H25G0.53270.38130.35890.081*0.50
C26G0.5583 (12)0.455 (5)0.4129 (8)0.056 (5)0.50
H26G0.52880.32690.42310.067*0.50
F12F0.2125 (3)0.2157 (14)0.46362 (12)0.0633 (15)0.50
O1F0.093 (2)0.407 (4)0.4964 (9)0.063 (5)0.50
C1F0.1132 (16)0.194 (3)0.4885 (4)0.040 (4)0.50
N1F0.1216 (5)0.0057 (16)0.51310 (17)0.0477 (19)0.50
H1F0.12820.15630.50430.057*0.50
C11F0.1171 (9)0.135 (3)0.4484 (3)0.053 (3)0.50
C12F0.1663 (7)0.065 (3)0.4380 (3)0.051 (3)0.50
C13F0.1714 (8)0.117 (3)0.3990 (3)0.056 (3)0.50
H13F0.20470.24900.39220.067*0.50
C14F0.127 (2)0.030 (7)0.3726 (8)0.078 (8)0.50
H14F0.13400.01650.34820.093*0.50
C15F0.071 (2)0.242 (7)0.3732 (8)0.130 (10)0.50
H15F0.04390.34150.35370.156*0.50
C16F0.071 (2)0.258 (6)0.4206 (9)0.068 (6)0.50
H16F0.03160.36960.42810.082*0.50
C21F0.1200 (10)0.020 (3)0.5523 (3)0.053 (3)0.50
C22F0.0768 (17)0.264 (7)0.5690 (7)0.070 (6)0.50
H22F0.04840.40500.55770.084*0.50
N23F0.0990 (12)0.180 (4)0.6095 (5)0.074 (5)0.50
C24F0.1347 (19)0.005 (6)0.6276 (9)0.073 (6)0.50
H24F0.13690.00910.65370.087*0.50
C25F0.1687 (10)0.190 (3)0.6109 (4)0.061 (4)0.50
H25F0.19520.32630.62450.073*0.50
C26F0.1639 (8)0.177 (2)0.5749 (3)0.054 (3)0.50
H26F0.19060.30340.56270.065*0.50
F12H0.2167 (4)0.2108 (17)0.53712 (14)0.0795 (19)0.50
O1H0.096 (2)0.420 (4)0.4897 (9)0.074 (7)0.50
C1H0.1070 (18)0.199 (4)0.5009 (4)0.052 (5)0.50
N1H0.1165 (5)0.0014 (19)0.4774 (2)0.053 (2)0.50
H1H0.12330.15100.48740.064*0.50
C11H0.1220 (9)0.136 (3)0.5426 (4)0.058 (3)0.50
C12H0.1732 (8)0.060 (3)0.5606 (3)0.055 (3)0.50
C13H0.1876 (9)0.110 (3)0.5993 (4)0.066 (4)0.50
H13H0.22060.24700.60900.079*0.50
C14H0.1517 (15)0.049 (6)0.6222 (8)0.074 (7)0.50
H14H0.16320.02140.64810.089*0.50
C15H0.0946 (16)0.267 (5)0.6084 (7)0.106 (9)0.50
H15H0.06900.39110.62150.128*0.50
C16H0.0923 (19)0.221 (6)0.5678 (9)0.077 (7)0.50
H16H0.04300.29790.55660.093*0.50
C21H0.1160 (10)0.016 (3)0.4387 (3)0.056 (3)0.50
C22H0.077 (2)0.208 (6)0.4128 (8)0.064 (6)0.50
H22H0.04720.34170.42190.076*0.50
N23H0.0818 (14)0.198 (3)0.3818 (4)0.066 (4)0.50
C24H0.1253 (18)0.025 (6)0.3641 (8)0.059 (5)0.50
H24H0.12830.02700.33840.071*0.50
C25H0.1557 (8)0.198 (3)0.3842 (3)0.054 (3)0.50
H25H0.17960.33940.37430.065*0.50
C26H0.1533 (7)0.177 (2)0.4207 (4)0.052 (3)0.50
H26H0.17940.30640.43600.063*0.50
F22W0.6211 (16)0.414 (8)0.1280 (7)0.096 (7)*0.13
O1W0.728 (4)0.243 (10)0.1790 (14)0.087 (17)*0.13
C1W0.710 (5)0.037 (10)0.1645 (8)0.090 (12)*0.13
N1W0.720 (3)0.181 (10)0.1866 (8)0.089 (9)*0.13
H1W0.72320.32530.17540.107*0.13
C11W0.727 (3)0.181 (9)0.2256 (8)0.084 (9)*0.13
C12W0.686 (2)0.376 (8)0.2419 (9)0.092 (10)*0.13
H12W0.65820.50370.22680.110*0.13
N13W0.686 (2)0.380 (9)0.2807 (10)0.093 (11)*0.13
C14W0.727 (3)0.190 (10)0.3032 (7)0.093 (12)*0.13
H14W0.72750.19260.32920.111*0.13
C15W0.768 (3)0.005 (9)0.2870 (13)0.085 (12)*0.13
H15W0.79600.13250.30200.101*0.13
C16W0.768 (3)0.009 (8)0.2481 (13)0.081 (11)*0.13
H16W0.79570.13950.23720.097*0.13
C21W0.692 (2)0.047 (7)0.1239 (6)0.067 (9)*0.13
C22W0.6505 (18)0.269 (6)0.1103 (7)0.060 (8)*0.13
C23W0.6474 (17)0.337 (6)0.0726 (8)0.043 (8)*0.13
H23W0.61970.48520.06360.051*0.13
C24W0.686 (3)0.184 (8)0.0485 (7)0.063 (12)*0.13
H24W0.68370.22920.02330.076*0.13
C25W0.727 (3)0.038 (7)0.0621 (9)0.070 (13)*0.13
H25W0.75290.14060.04600.084*0.13
C26W0.730 (2)0.106 (6)0.0998 (9)0.068 (11)*0.13
H26W0.75810.25450.10890.081*0.13
F22X0.1227 (10)0.279 (4)0.2033 (4)0.073 (4)*0.17
O1X0.231 (4)0.901 (8)0.1761 (14)0.055 (11)*0.17
C1X0.219 (4)0.678 (8)0.1819 (8)0.076 (10)*0.17
N1X0.2114 (17)0.495 (7)0.1552 (6)0.081 (7)*0.17
H1X0.20590.34170.16340.097*0.17
C11X0.211 (2)0.513 (8)0.1171 (6)0.100 (8)*0.17
C12X0.1664 (18)0.331 (7)0.0941 (8)0.100 (9)*0.17
H12X0.13820.20140.10480.120*0.17
N13X0.1636 (18)0.343 (7)0.0552 (8)0.117 (9)*0.17
C14X0.206 (2)0.537 (8)0.0392 (6)0.120 (10)*0.17
H14X0.20390.54540.01310.144*0.17
C15X0.250 (2)0.719 (7)0.0622 (10)0.118 (11)*0.17
H15X0.27860.84910.05150.141*0.17
C16X0.253 (2)0.707 (7)0.1011 (9)0.109 (10)*0.17
H16X0.28310.82890.11650.131*0.17
C21X0.215 (2)0.654 (8)0.2226 (7)0.102 (11)*0.17
C22X0.166 (2)0.446 (7)0.2299 (7)0.101 (10)*0.17
C23X0.1607 (17)0.376 (6)0.2669 (9)0.068 (9)*0.17
H23X0.12790.23770.27180.081*0.17
C24X0.204 (3)0.514 (8)0.2966 (6)0.091 (13)*0.17
H24X0.20090.46730.32140.109*0.17
C25X0.253 (3)0.721 (8)0.2893 (9)0.100 (15)*0.17
H25X0.28270.81340.30920.120*0.17
C26X0.259 (2)0.791 (7)0.2523 (11)0.098 (13)*0.17
H26X0.29140.92990.24740.117*0.17
F22Y1.0551 (10)0.886 (5)0.1231 (4)0.080 (5)*0.17
O1Y0.9538 (16)0.269 (5)0.1555 (9)0.058 (9)*0.17
C1Y0.939 (2)0.488 (5)0.1435 (6)0.057 (6)*0.17
N1Y0.9452 (15)0.670 (5)0.1716 (5)0.053 (5)*0.17
H1Y0.93440.83000.16820.064*0.17
C11Y0.9727 (18)0.550 (5)0.2073 (5)0.034 (5)*0.17
C12Y1.0197 (14)0.742 (5)0.2273 (5)0.016 (5)*0.17
H12Y1.05140.85250.21480.019*0.17
N13Y1.0191 (13)0.768 (5)0.2659 (5)0.019 (5)*0.17
C14Y0.9716 (19)0.603 (7)0.2845 (6)0.029 (6)*0.17
H14Y0.97130.62060.31030.035*0.17
C15Y0.925 (2)0.411 (6)0.2645 (8)0.030 (6)*0.17
H15Y0.89290.30080.27700.036*0.17
C16Y0.925 (2)0.385 (5)0.2260 (8)0.035 (6)*0.17
H16Y0.89380.25690.21260.043*0.17
C21Y0.9513 (13)0.604 (5)0.1054 (5)0.018 (6)*0.17
C22Y1.0102 (11)0.777 (5)0.0960 (5)0.040 (6)*0.17
C23Y1.0135 (15)0.835 (6)0.0584 (6)0.059 (9)*0.17
H23Y1.05290.95010.05210.071*0.17
C24Y0.9578 (19)0.720 (8)0.0301 (4)0.046 (12)*0.17
H24Y0.96000.75810.00490.056*0.17
C25Y0.8989 (19)0.547 (8)0.0395 (6)0.039 (10)*0.17
H25Y0.86160.46990.02060.047*0.17
C26Y0.8956 (15)0.489 (6)0.0772 (7)0.035 (9)*0.17
H26Y0.85620.37370.08340.042*0.17
F22Z0.5572 (15)0.196 (7)0.2006 (6)0.092 (7)*0.13
O1Z0.412 (3)0.398 (7)0.1594 (12)0.033 (8)*0.13
C1Z0.435 (3)0.182 (8)0.1668 (8)0.052 (9)*0.13
N1Z0.4546 (19)0.015 (7)0.1403 (6)0.062 (6)*0.13
H1Z0.46690.13740.14840.074*0.13
C11Z0.457 (3)0.054 (8)0.1028 (6)0.055 (7)*0.13
C12Z0.486 (2)0.151 (7)0.0837 (8)0.060 (8)*0.13
H12Z0.50840.29410.09700.072*0.13
N13Z0.4818 (19)0.143 (7)0.0447 (8)0.068 (8)*0.13
C14Z0.449 (3)0.070 (9)0.0247 (6)0.063 (10)*0.13
H14Z0.44570.07570.00140.075*0.13
C15Z0.420 (3)0.276 (8)0.0438 (11)0.065 (10)*0.13
H15Z0.39740.41850.03040.079*0.13
C16Z0.424 (3)0.268 (7)0.0828 (11)0.063 (10)*0.13
H16Z0.40450.40500.09560.075*0.13
C21Z0.449 (5)0.144 (19)0.2090 (10)0.20 (3)*0.13
C22Z0.517 (5)0.015 (16)0.221 (2)0.21 (3)*0.13
C23Z0.546 (3)0.043 (13)0.259 (2)0.21 (3)*0.13
H23Z0.59110.14950.26670.258*0.13
C24Z0.508 (5)0.089 (17)0.2854 (11)0.21 (3)*0.13
H24Z0.52750.07060.31100.252*0.13
C25Z0.440 (5)0.248 (15)0.2738 (19)0.21 (3)*0.13
H25Z0.41480.33670.29150.249*0.13
C26Z0.411 (4)0.276 (15)0.236 (2)0.21 (3)*0.13
H26Z0.36580.38270.22770.247*0.13
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F12A0.0686 (18)0.064 (3)0.0654 (16)0.024 (2)0.0162 (13)0.0040 (18)
O1A0.097 (4)0.037 (3)0.051 (3)0.016 (3)0.016 (3)0.005 (2)
C1A0.059 (4)0.040 (4)0.056 (3)0.005 (3)0.012 (3)0.003 (3)
N1A0.061 (3)0.043 (3)0.044 (2)0.008 (2)0.0128 (17)0.005 (2)
C11A0.049 (3)0.039 (4)0.043 (2)0.004 (3)0.0024 (19)0.014 (3)
C12A0.060 (3)0.028 (3)0.047 (2)0.003 (3)0.003 (2)0.008 (2)
C13A0.061 (3)0.050 (4)0.066 (3)0.005 (3)0.021 (3)0.007 (3)
C14A0.107 (5)0.063 (5)0.048 (3)0.003 (5)0.016 (3)0.004 (3)
C15A0.076 (5)0.078 (6)0.058 (3)0.013 (5)0.001 (3)0.035 (4)
C16A0.065 (3)0.036 (4)0.062 (3)0.010 (3)0.006 (2)0.005 (3)
C21A0.039 (2)0.024 (3)0.047 (2)0.000 (2)0.0104 (19)0.006 (2)
C22A0.067 (3)0.056 (5)0.050 (3)0.006 (3)0.012 (3)0.021 (3)
N23A0.088 (3)0.042 (3)0.039 (2)0.001 (3)0.007 (2)0.002 (2)
C24A0.098 (5)0.058 (5)0.043 (3)0.016 (4)0.021 (3)0.009 (3)
C25A0.079 (4)0.040 (4)0.061 (3)0.007 (4)0.027 (3)0.020 (3)
C26A0.057 (3)0.025 (3)0.059 (3)0.005 (3)0.015 (2)0.007 (2)
F12B0.078 (2)0.063 (2)0.0469 (14)0.025 (2)0.0041 (13)0.0053 (16)
O1B0.085 (5)0.033 (3)0.059 (4)0.001 (3)0.001 (3)0.002 (3)
C1B0.050 (3)0.023 (4)0.046 (3)0.012 (3)0.003 (3)0.001 (3)
N1B0.068 (3)0.024 (3)0.034 (2)0.003 (2)0.0023 (18)0.005 (2)
C11B0.051 (3)0.023 (3)0.040 (2)0.006 (2)0.003 (2)0.000 (2)
C12B0.053 (3)0.039 (4)0.054 (3)0.002 (3)0.008 (2)0.008 (3)
C13B0.069 (3)0.046 (4)0.043 (3)0.003 (3)0.001 (2)0.008 (3)
C14B0.077 (4)0.042 (4)0.037 (2)0.004 (3)0.007 (2)0.004 (3)
C15B0.080 (4)0.067 (5)0.053 (3)0.002 (4)0.028 (3)0.013 (3)
C16B0.055 (3)0.044 (4)0.047 (2)0.004 (3)0.014 (2)0.001 (3)
C21B0.054 (3)0.042 (4)0.044 (3)0.007 (3)0.017 (2)0.004 (3)
C22B0.072 (4)0.031 (3)0.039 (3)0.003 (3)0.015 (2)0.005 (2)
N23B0.077 (3)0.061 (4)0.043 (2)0.012 (3)0.017 (2)0.009 (3)
C24B0.076 (4)0.049 (4)0.045 (3)0.014 (3)0.013 (3)0.005 (3)
C25B0.075 (4)0.059 (5)0.050 (3)0.000 (4)0.001 (3)0.013 (3)
C26B0.060 (3)0.033 (4)0.049 (3)0.015 (3)0.011 (2)0.007 (3)
F12C0.083 (2)0.059 (2)0.0535 (15)0.028 (2)0.0021 (14)0.0036 (17)
O1C0.070 (4)0.037 (3)0.054 (3)0.017 (3)0.012 (2)0.0036 (19)
C1C0.052 (3)0.046 (5)0.053 (3)0.008 (3)0.019 (3)0.001 (3)
N1C0.069 (3)0.031 (3)0.044 (2)0.002 (2)0.0184 (19)0.002 (2)
C11C0.036 (4)0.079 (6)0.044 (3)0.013 (4)0.007 (2)0.009 (3)
C12C0.049 (4)0.082 (6)0.057 (4)0.003 (4)0.003 (3)0.032 (4)
C13C0.107 (7)0.071 (8)0.081 (5)0.013 (6)0.016 (4)0.039 (5)
C14C0.102 (7)0.067 (7)0.047 (3)0.012 (5)0.010 (3)0.000 (4)
C15C0.087 (6)0.053 (6)0.052 (4)0.002 (4)0.024 (4)0.015 (4)
C16C0.076 (4)0.061 (5)0.060 (5)0.012 (4)0.023 (3)0.002 (4)
C21C0.055 (4)0.022 (3)0.044 (3)0.013 (3)0.005 (2)0.003 (2)
C22C0.057 (3)0.045 (4)0.048 (3)0.007 (3)0.002 (2)0.015 (3)
N23C0.085 (4)0.036 (3)0.045 (2)0.003 (3)0.014 (2)0.001 (2)
C24C0.115 (8)0.063 (6)0.037 (3)0.005 (5)0.013 (3)0.005 (3)
C25C0.065 (5)0.047 (5)0.053 (4)0.006 (4)0.008 (3)0.019 (3)
C26C0.060 (4)0.073 (6)0.052 (4)0.003 (4)0.007 (3)0.003 (3)
F12D0.0782 (19)0.076 (3)0.0582 (15)0.034 (2)0.0142 (14)0.0043 (18)
O1D0.092 (6)0.035 (4)0.083 (4)0.006 (3)0.021 (3)0.001 (3)
C1D0.046 (3)0.029 (4)0.056 (3)0.004 (3)0.006 (2)0.002 (3)
N1D0.064 (3)0.023 (3)0.055 (2)0.005 (2)0.0151 (19)0.004 (2)
C11D0.048 (3)0.025 (3)0.061 (3)0.008 (2)0.015 (2)0.005 (3)
C12D0.045 (3)0.052 (4)0.063 (3)0.002 (3)0.015 (3)0.002 (3)
C13D0.066 (3)0.057 (4)0.051 (3)0.014 (3)0.020 (3)0.006 (3)
C14D0.089 (4)0.066 (6)0.047 (3)0.011 (5)0.007 (3)0.016 (4)
C15D0.089 (5)0.073 (6)0.065 (4)0.007 (5)0.001 (3)0.020 (4)
C16D0.067 (5)0.063 (5)0.072 (4)0.006 (4)0.008 (3)0.021 (4)
C21D0.045 (3)0.062 (4)0.047 (2)0.015 (3)0.008 (2)0.010 (3)
C22D0.063 (3)0.033 (3)0.055 (3)0.004 (3)0.008 (2)0.005 (2)
N23D0.071 (3)0.060 (4)0.063 (3)0.001 (3)0.005 (2)0.006 (3)
C24D0.060 (3)0.051 (4)0.051 (3)0.000 (3)0.001 (2)0.014 (3)
C25D0.060 (3)0.061 (5)0.057 (3)0.001 (3)0.022 (2)0.017 (3)
C26D0.043 (3)0.056 (4)0.049 (2)0.004 (3)0.012 (2)0.007 (3)
F12E0.070 (3)0.074 (4)0.049 (2)0.031 (3)0.016 (2)0.014 (3)
O1E0.083 (16)0.036 (9)0.060 (8)0.026 (9)0.017 (8)0.005 (7)
C1E0.056 (6)0.050 (9)0.040 (6)0.001 (5)0.006 (6)0.006 (6)
N1E0.081 (5)0.038 (6)0.032 (4)0.009 (4)0.013 (3)0.006 (4)
C11E0.047 (7)0.054 (10)0.031 (5)0.000 (7)0.004 (4)0.001 (6)
C12E0.062 (7)0.046 (7)0.026 (6)0.013 (6)0.009 (5)0.011 (4)
C13E0.080 (10)0.078 (13)0.059 (10)0.015 (9)0.014 (8)0.003 (8)
C14E0.055 (12)0.082 (13)0.047 (8)0.016 (8)0.015 (8)0.000 (8)
C15E0.063 (16)0.070 (11)0.045 (8)0.006 (11)0.008 (9)0.027 (7)
C16E0.029 (9)0.060 (9)0.050 (6)0.011 (7)0.009 (7)0.009 (6)
C21E0.044 (7)0.017 (6)0.043 (5)0.002 (5)0.012 (5)0.009 (4)
C22E0.063 (7)0.044 (8)0.033 (6)0.013 (6)0.006 (5)0.009 (5)
N23E0.077 (7)0.047 (7)0.030 (5)0.002 (5)0.007 (4)0.002 (4)
C24E0.080 (9)0.053 (11)0.033 (7)0.006 (9)0.023 (5)0.004 (6)
C25E0.059 (13)0.042 (12)0.060 (9)0.011 (10)0.029 (10)0.019 (8)
C26E0.070 (8)0.044 (7)0.060 (11)0.023 (6)0.042 (8)0.004 (7)
F12G0.094 (4)0.080 (5)0.065 (3)0.038 (4)0.000 (3)0.002 (3)
O1G0.083 (17)0.038 (8)0.071 (10)0.003 (6)0.007 (9)0.001 (7)
C1G0.055 (7)0.049 (9)0.061 (8)0.018 (6)0.015 (8)0.003 (7)
N1G0.076 (6)0.051 (7)0.070 (6)0.006 (5)0.018 (4)0.001 (5)
C11G0.041 (6)0.073 (11)0.057 (6)0.002 (7)0.005 (5)0.009 (7)
C12G0.052 (7)0.045 (8)0.038 (6)0.003 (6)0.006 (5)0.003 (5)
C13G0.057 (7)0.057 (9)0.056 (9)0.001 (6)0.000 (6)0.010 (7)
C14G0.086 (10)0.060 (12)0.036 (9)0.030 (8)0.010 (7)0.001 (7)
C15G0.053 (11)0.048 (13)0.050 (9)0.014 (9)0.003 (7)0.015 (8)
C16G0.060 (10)0.121 (15)0.031 (7)0.003 (9)0.008 (7)0.001 (8)
C21G0.061 (8)0.052 (10)0.039 (6)0.022 (8)0.001 (6)0.000 (6)
C22G0.082 (8)0.067 (10)0.040 (7)0.022 (8)0.005 (6)0.016 (7)
N23G0.103 (11)0.063 (10)0.057 (9)0.019 (8)0.021 (7)0.025 (7)
C24G0.068 (16)0.078 (12)0.062 (8)0.001 (10)0.006 (8)0.046 (8)
C25G0.056 (14)0.083 (14)0.065 (10)0.005 (11)0.014 (9)0.024 (10)
C26G0.030 (10)0.074 (10)0.062 (7)0.020 (8)0.003 (7)0.018 (6)
F12F0.077 (3)0.070 (4)0.046 (2)0.029 (3)0.020 (2)0.013 (3)
O1F0.091 (9)0.027 (8)0.076 (9)0.014 (6)0.033 (7)0.001 (6)
C1F0.041 (7)0.021 (9)0.059 (7)0.003 (5)0.011 (8)0.004 (6)
N1F0.082 (5)0.023 (5)0.041 (4)0.004 (4)0.016 (3)0.005 (3)
C11F0.061 (7)0.044 (8)0.060 (6)0.005 (6)0.026 (5)0.008 (6)
C12F0.041 (5)0.068 (8)0.048 (6)0.005 (6)0.023 (5)0.012 (5)
C13F0.082 (7)0.058 (8)0.034 (7)0.015 (7)0.025 (6)0.009 (6)
C14F0.106 (13)0.084 (18)0.048 (10)0.007 (12)0.030 (8)0.008 (10)
C15F0.130 (17)0.16 (2)0.104 (14)0.012 (13)0.037 (14)0.016 (14)
C16F0.075 (10)0.079 (15)0.056 (9)0.000 (10)0.026 (7)0.013 (9)
C21F0.062 (8)0.050 (9)0.050 (6)0.011 (8)0.018 (6)0.012 (6)
C22F0.060 (14)0.100 (11)0.052 (7)0.017 (9)0.012 (8)0.045 (7)
N23F0.088 (10)0.069 (10)0.078 (7)0.011 (7)0.055 (7)0.036 (6)
C24F0.083 (14)0.062 (11)0.072 (9)0.018 (8)0.008 (8)0.005 (7)
C25F0.074 (8)0.053 (8)0.057 (8)0.002 (6)0.015 (5)0.006 (6)
C26F0.092 (8)0.020 (5)0.053 (6)0.007 (5)0.024 (6)0.008 (5)
F12H0.088 (4)0.082 (5)0.066 (3)0.031 (4)0.002 (3)0.007 (3)
O1H0.090 (11)0.046 (10)0.084 (12)0.017 (7)0.003 (8)0.014 (6)
C1H0.046 (7)0.041 (12)0.071 (8)0.007 (6)0.021 (9)0.017 (7)
N1H0.074 (5)0.030 (5)0.054 (5)0.001 (4)0.004 (3)0.005 (4)
C11H0.054 (6)0.038 (8)0.085 (7)0.022 (6)0.018 (6)0.002 (6)
C12H0.054 (6)0.057 (8)0.056 (6)0.004 (7)0.009 (5)0.008 (6)
C13H0.073 (8)0.067 (10)0.056 (8)0.011 (7)0.001 (6)0.019 (7)
C14H0.056 (10)0.083 (16)0.079 (11)0.029 (12)0.012 (8)0.021 (10)
C15H0.121 (14)0.083 (16)0.102 (10)0.019 (11)0.029 (9)0.004 (10)
C16H0.039 (8)0.112 (17)0.090 (10)0.016 (9)0.038 (7)0.013 (11)
C21H0.052 (7)0.057 (9)0.062 (7)0.011 (8)0.024 (6)0.000 (6)
C22H0.079 (9)0.054 (10)0.062 (13)0.040 (8)0.026 (9)0.020 (9)
N23H0.090 (8)0.057 (7)0.046 (6)0.004 (6)0.002 (5)0.027 (6)
C24H0.060 (8)0.052 (11)0.071 (12)0.002 (7)0.029 (8)0.005 (9)
C25H0.067 (7)0.050 (8)0.048 (7)0.002 (6)0.018 (5)0.008 (6)
C26H0.073 (7)0.038 (6)0.049 (6)0.007 (5)0.018 (5)0.006 (5)
Geometric parameters (Å, º) top
F12A—C12A1.364 (6)F12F—C12F1.350 (14)
O1A—C1A1.249 (9)O1F—C1F1.206 (16)
C1A—N1A1.339 (8)C1F—N1F1.361 (14)
C1A—C11A1.533 (8)C1F—C11F1.478 (15)
N1A—C21A1.387 (5)N1F—C21F1.413 (12)
N1A—H1A0.8600N1F—H1F0.8600
C11A—C12A1.364 (8)C11F—C16F1.32 (4)
C11A—C16A1.423 (8)C11F—C12F1.396 (19)
C12A—C13A1.355 (7)C12F—C13F1.437 (14)
C13A—C14A1.438 (9)C13F—C14F1.34 (4)
C13A—H13A0.9300C13F—H13F0.9300
C14A—C15A1.337 (10)C14F—C15F1.43 (5)
C14A—H14A0.9300C14F—H14F0.9300
C15A—C16A1.395 (7)C15F—C16F1.70 (4)
C15A—H15A0.9300C15F—H15F0.9300
C16A—H16A0.9300C16F—H16F0.9300
C21A—C22A1.359 (8)C21F—C26F1.435 (19)
C21A—C26A1.411 (7)C21F—C22F1.61 (3)
C22A—N23A1.368 (6)C22F—N23F1.51 (3)
C22A—H22A0.9300C22F—H22F0.9300
N23A—C24A1.339 (9)N23F—C24F1.26 (4)
C24A—C25A1.404 (10)C24F—C25F1.30 (4)
C24A—H24A0.9300C24F—H24F0.9300
C25A—C26A1.346 (7)C25F—C26F1.284 (18)
C25A—H25A0.9300C25F—H25F0.9300
C26A—H26A0.9300C26F—H26F0.9300
F12B—C12B1.355 (7)F12H—C12H1.412 (14)
O1B—C1B1.231 (10)O1H—C1H1.227 (18)
C1B—N1B1.352 (8)C1H—N1H1.365 (15)
C1B—C11B1.491 (7)C1H—C11H1.514 (16)
N1B—C21B1.411 (6)N1H—C21H1.386 (12)
N1B—H1B0.8600N1H—H1H0.8600
C11B—C16B1.369 (8)C11H—C16H1.17 (3)
C11B—C12B1.427 (8)C11H—C12H1.41 (2)
C12B—C13B1.371 (7)C12H—C13H1.396 (18)
C13B—C14B1.370 (9)C13H—C14H1.36 (3)
C13B—H13B0.9300C13H—H13H0.9300
C14B—C15B1.366 (10)C14H—C15H1.51 (3)
C14B—H14B0.9300C14H—H14H0.9300
C15B—C16B1.397 (7)C15H—C16H1.47 (4)
C15B—H15B0.9300C15H—H15H0.9300
C16B—H16B0.9300C16H—H16H0.9300
C21B—C26B1.344 (8)C21H—C26H1.385 (17)
C21B—C22B1.398 (8)C21H—C22H1.45 (3)
C22B—N23B1.344 (6)C22H—N23H1.13 (3)
C22B—H22B0.9300C22H—H22H0.9300
N23B—C24B1.250 (9)N23H—C24H1.54 (3)
C24B—C25B1.432 (10)C24H—C25H1.21 (3)
C24B—H24B0.9300C24H—H24H0.9300
C25B—C26B1.360 (7)C25H—C26H1.317 (16)
C25B—H25B0.9300C25H—H25H0.9300
C26B—H26B0.9300C26H—H26H0.9300
F12C—C12C1.367 (8)F22W—C22W1.14 (4)
O1C—C1C1.236 (10)O1W—C1W1.21 (2)
C1C—N1C1.360 (8)C1W—N1W1.38 (2)
C1C—C11C1.548 (8)C1W—C21W1.51 (2)
N1C—C21C1.417 (6)N1W—C11W1.38 (2)
N1C—H1C0.8600N1W—H1W0.8600
C11C—C12C1.314 (10)C11W—C12W1.3900
C11C—C16C1.415 (9)C11W—C16W1.3900
C12C—C13C1.423 (9)C12W—N13W1.3900
C13C—C14C1.350 (12)C12W—H12W0.9300
C13C—H13C0.9300N13W—C14W1.3900
C14C—C15C1.400 (11)C14W—C15W1.3900
C14C—H14C0.9300C14W—H14W0.9300
C15C—C16C1.358 (8)C15W—C16W1.3900
C15C—H15C0.9300C15W—H15W0.9300
C16C—H16C0.9300C16W—H16W0.9300
C21C—C22C1.356 (9)C21W—C22W1.3900
C21C—C26C1.409 (11)C21W—C26W1.3900
C22C—N23C1.326 (6)C22W—C23W1.3900
C22C—H22C0.9300C23W—C24W1.3900
N23C—C24C1.409 (11)C23W—H23W0.9300
C24C—C25C1.292 (10)C24W—C25W1.3900
C24C—H24C0.9300C24W—H24W0.9300
C25C—C26C1.413 (7)C25W—C26W1.3900
C25C—H25C0.9300C25W—H25W0.9300
C26C—H26C0.9300C26W—H26W0.9300
F12D—C12D1.365 (7)F22X—C22X1.40 (3)
O1D—C1D1.212 (9)O1X—C1X1.20 (2)
C1D—N1D1.372 (8)C1X—N1X1.349 (19)
C1D—C11D1.468 (7)C1X—C21X1.47 (2)
N1D—C21D1.406 (6)N1X—C11X1.368 (18)
N1D—H1D0.8600N1X—H1X0.8600
C11D—C16D1.370 (8)C11X—C12X1.3900
C11D—C12D1.414 (9)C11X—C16X1.3900
C12D—C13D1.378 (7)C12X—N13X1.3900
C13D—C14D1.283 (9)C12X—H12X0.9300
C13D—H13D0.9300N13X—C14X1.3900
C14D—C15D1.421 (12)C14X—C15X1.3900
C14D—H14D0.9300C14X—H14X0.9300
C15D—C16D1.376 (8)C15X—C16X1.3900
C15D—H15D0.9300C15X—H15X0.9300
C16D—H16D0.9300C16X—H16X0.9300
C21D—C26D1.353 (8)C21X—C22X1.3900
C21D—C22D1.423 (8)C21X—C26X1.3900
C22D—N23D1.316 (6)C22X—C23X1.3900
C22D—H22D0.9300C23X—C24X1.3900
N23D—C24D1.332 (8)C23X—H23X0.9300
C24D—C25D1.318 (9)C24X—C25X1.3900
C24D—H24D0.9300C24X—H24X0.9300
C25D—C26D1.418 (6)C25X—C26X1.3900
C25D—H25D0.9300C25X—H25X0.9300
C26D—H26D0.9300C26X—H26X0.9300
F12E—C12E1.343 (15)F22Y—C22Y1.26 (2)
O1E—C1E1.226 (19)O1Y—C1Y1.235 (19)
C1E—N1E1.361 (14)C1Y—N1Y1.375 (19)
C1E—C11E1.538 (14)C1Y—C21Y1.535 (18)
N1E—C21E1.396 (12)N1Y—C11Y1.436 (19)
N1E—H1E0.8600N1Y—H1Y0.8600
C11E—C12E1.28 (2)C11Y—C12Y1.3900
C11E—C16E1.38 (3)C11Y—C16Y1.3900
C12E—C13E1.41 (2)C12Y—N13Y1.3900
C13E—C14E1.39 (4)C12Y—H12Y0.9300
C13E—H13E0.9300N13Y—C14Y1.3900
C14E—C15E1.33 (6)C14Y—C15Y1.3900
C14E—H14E0.9300C14Y—H14Y0.9300
C15E—C16E1.44 (5)C15Y—C16Y1.3900
C15E—H15E0.9300C15Y—H15Y0.9300
C16E—H16E0.9300C16Y—H16Y0.9300
C21E—C22E1.346 (18)C21Y—C22Y1.3900
C21E—C26E1.54 (2)C21Y—C26Y1.3900
C22E—N23E1.378 (15)C22Y—C23Y1.3900
C22E—H22E0.9300C23Y—C24Y1.3900
N23E—C24E1.31 (3)C23Y—H23Y0.9300
C24E—C25E1.48 (5)C24Y—C25Y1.3900
C24E—H24E0.9300C24Y—H24Y0.9300
C25E—C26E1.23 (5)C25Y—C26Y1.3900
C25E—H25E0.9300C25Y—H25Y0.9300
C26E—H26E0.9300C26Y—H26Y0.9300
F12G—C12G1.360 (15)F22Z—C22Z1.41 (6)
O1G—C1G1.23 (2)O1Z—C1Z1.21 (2)
C1G—N1G1.355 (14)C1Z—N1Z1.36 (2)
C1G—C11G1.506 (15)C1Z—C21Z1.51 (2)
N1G—C21G1.414 (14)N1Z—C11Z1.368 (19)
N1G—H1G0.8600N1Z—H1Z0.8600
C11G—C16G1.24 (3)C11Z—C12Z1.3900
C11G—C12G1.30 (2)C11Z—C16Z1.3900
C12G—C13G1.391 (18)C12Z—N13Z1.3900
C13G—C14G1.43 (3)C12Z—H12Z0.9300
C13G—H13G0.9300N13Z—C14Z1.3900
C14G—C15G1.27 (5)C14Z—C15Z1.3900
C14G—H14G0.9300C14Z—H14Z0.9300
C15G—C16G1.48 (5)C15Z—C16Z1.3900
C15G—H15G0.9300C15Z—H15Z0.9300
C16G—H16G0.9300C16Z—H16Z0.9300
C21G—C22G1.35 (3)C21Z—C22Z1.3900
C21G—C26G1.52 (3)C21Z—C26Z1.3900
C22G—N23G1.31 (2)C22Z—C23Z1.3900
C22G—H22G0.9300C23Z—C24Z1.3900
N23G—C24G1.52 (3)C23Z—H23Z0.9300
C24G—C25G1.28 (6)C24Z—C25Z1.3900
C24G—H24G0.9300C24Z—H24Z0.9300
C25G—C26G1.37 (5)C25Z—C26Z1.3900
C25G—H25G0.9300C25Z—H25Z0.9300
C26G—H26G0.9300C26Z—H26Z0.9300
O1A—C1A—N1A122.2 (6)O1F—C1F—N1F124.0 (19)
O1A—C1A—C11A121.9 (6)O1F—C1F—C11F118.3 (18)
N1A—C1A—C11A115.9 (6)N1F—C1F—C11F117.0 (13)
C1A—N1A—C21A128.7 (5)C1F—N1F—C21F123.7 (11)
C1A—N1A—H1A115.7C1F—N1F—H1F118.1
C21A—N1A—H1A115.7C21F—N1F—H1F118.1
C12A—C11A—C16A117.6 (4)C16F—C11F—C12F116.4 (15)
C12A—C11A—C1A127.1 (5)C16F—C11F—C1F121.9 (18)
C16A—C11A—C1A114.9 (5)C12F—C11F—C1F121.5 (13)
C13A—C12A—C11A125.7 (5)F12F—C12F—C11F122.4 (10)
C13A—C12A—F12A117.0 (5)F12F—C12F—C13F116.4 (13)
C11A—C12A—F12A117.3 (4)C11F—C12F—C13F121.2 (12)
C12A—C13A—C14A115.8 (6)C14F—C13F—C12F118.4 (17)
C12A—C13A—H13A122.1C14F—C13F—H13F120.8
C14A—C13A—H13A122.1C12F—C13F—H13F120.8
C15A—C14A—C13A120.1 (5)C13F—C14F—C15F135 (2)
C15A—C14A—H14A119.9C13F—C14F—H14F112.6
C13A—C14A—H14A119.9C15F—C14F—H14F112.6
C14A—C15A—C16A123.1 (6)C14F—C15F—C16F99 (2)
C14A—C15A—H15A118.5C14F—C15F—H15F130.7
C16A—C15A—H15A118.5C16F—C15F—H15F130.7
C15A—C16A—C11A117.4 (6)C11F—C16F—C15F130 (2)
C15A—C16A—H16A121.3C11F—C16F—H16F115.0
C11A—C16A—H16A121.3C15F—C16F—H16F115.0
C22A—C21A—N1A117.1 (5)N1F—C21F—C26F114.3 (13)
C22A—C21A—C26A117.8 (4)N1F—C21F—C22F121.1 (16)
N1A—C21A—C26A125.0 (5)C26F—C21F—C22F124.5 (14)
C21A—C22A—N23A124.5 (5)N23F—C22F—C21F94 (2)
C21A—C22A—H22A117.8N23F—C22F—H22F132.9
N23A—C22A—H22A117.8C21F—C22F—H22F132.9
C24A—N23A—C22A115.6 (6)C24F—N23F—C22F138 (2)
N23A—C24A—C25A123.8 (5)N23F—C24F—C25F122 (3)
N23A—C24A—H24A118.1N23F—C24F—H24F119.0
C25A—C24A—H24A118.1C25F—C24F—H24F119.0
C26A—C25A—C24A118.7 (6)C26F—C25F—C24F117.0 (19)
C26A—C25A—H25A120.6C26F—C25F—H25F121.5
C24A—C25A—H25A120.6C24F—C25F—H25F121.5
C25A—C26A—C21A119.6 (5)C25F—C26F—C21F123.9 (12)
C25A—C26A—H26A120.2C25F—C26F—H26F118.1
C21A—C26A—H26A120.2C21F—C26F—H26F118.1
O1B—C1B—N1B122.1 (7)O1H—C1H—N1H123.0 (19)
O1B—C1B—C11B120.6 (7)O1H—C1H—C11H121 (2)
N1B—C1B—C11B117.2 (5)N1H—C1H—C11H115.4 (14)
C1B—N1B—C21B126.0 (5)C1H—N1H—C21H125.5 (12)
C1B—N1B—H1B117.0C1H—N1H—H1H117.3
C21B—N1B—H1B117.0C21H—N1H—H1H117.3
C16B—C11B—C12B116.1 (4)C16H—C11H—C12H102 (2)
C16B—C11B—C1B120.1 (5)C16H—C11H—C1H131 (2)
C12B—C11B—C1B123.6 (5)C12H—C11H—C1H127.2 (14)
F12B—C12B—C13B118.6 (5)C13H—C12H—F12H117.5 (14)
F12B—C12B—C11B119.2 (4)C13H—C12H—C11H126.0 (13)
C13B—C12B—C11B122.2 (5)F12H—C12H—C11H116.4 (10)
C14B—C13B—C12B119.2 (6)C14H—C13H—C12H117.6 (17)
C14B—C13B—H13B120.4C14H—C13H—H13H121.2
C12B—C13B—H13B120.4C12H—C13H—H13H121.2
C15B—C14B—C13B120.6 (5)C13H—C14H—C15H124 (2)
C15B—C14B—H14B119.7C13H—C14H—H14H117.9
C13B—C14B—H14B119.7C15H—C14H—H14H117.9
C14B—C15B—C16B119.9 (6)C16H—C15H—C14H97 (2)
C14B—C15B—H15B120.0C16H—C15H—H15H131.3
C16B—C15B—H15B120.0C14H—C15H—H15H131.3
C11B—C16B—C15B121.8 (6)C11H—C16H—C15H151 (3)
C11B—C16B—H16B119.1C11H—C16H—H16H104.7
C15B—C16B—H16B119.1C15H—C16H—H16H104.7
C26B—C21B—C22B117.3 (5)C26H—C21H—N1H118.5 (13)
C26B—C21B—N1B127.3 (5)C26H—C21H—C22H112.8 (12)
C22B—C21B—N1B115.2 (5)N1H—C21H—C22H128.5 (15)
N23B—C22B—C21B123.2 (6)N23H—C22H—C21H121 (2)
N23B—C22B—H22B118.4N23H—C22H—H22H119.7
C21B—C22B—H22B118.4C21H—C22H—H22H119.7
C24B—N23B—C22B118.0 (6)C22H—N23H—C24H123 (2)
N23B—C24B—C25B123.8 (6)C25H—C24H—N23H119 (2)
N23B—C24B—H24B118.1C25H—C24H—H24H120.4
C25B—C24B—H24B118.1N23H—C24H—H24H120.4
C26B—C25B—C24B117.1 (6)C24H—C25H—C26H117.3 (16)
C26B—C25B—H25B121.5C24H—C25H—H25H121.3
C24B—C25B—H25B121.5C26H—C25H—H25H121.3
C21B—C26B—C25B120.5 (6)C25H—C26H—C21H126.9 (12)
C21B—C26B—H26B119.8C25H—C26H—H26H116.6
C25B—C26B—H26B119.8C21H—C26H—H26H116.6
O1C—C1C—N1C124.3 (6)O1W—C1W—N1W119 (3)
O1C—C1C—C11C123.1 (6)O1W—C1W—C21W132 (4)
N1C—C1C—C11C112.4 (7)N1W—C1W—C21W108 (3)
C1C—N1C—C21C126.8 (6)C1W—N1W—C11W124 (4)
C1C—N1C—H1C116.6C1W—N1W—H1W117.8
C21C—N1C—H1C116.6C11W—N1W—H1W117.8
C12C—C11C—C16C115.9 (5)N1W—C11W—C12W117 (4)
C12C—C11C—C1C127.7 (6)N1W—C11W—C16W123 (4)
C16C—C11C—C1C116.1 (7)C12W—C11W—C16W120.0
C11C—C12C—F12C119.4 (6)N13W—C12W—C11W120.0
C11C—C12C—C13C126.8 (7)N13W—C12W—H12W120.0
F12C—C12C—C13C113.4 (8)C11W—C12W—H12W120.0
C14C—C13C—C12C115.1 (9)C12W—N13W—C14W120.0
C14C—C13C—H13C122.5C15W—C14W—N13W120.0
C12C—C13C—H13C122.5C15W—C14W—H14W120.0
C13C—C14C—C15C121.1 (6)N13W—C14W—H14W120.0
C13C—C14C—H14C119.5C16W—C15W—C14W120.0
C15C—C14C—H14C119.5C16W—C15W—H15W120.0
C16C—C15C—C14C120.5 (6)C14W—C15W—H15W120.0
C16C—C15C—H15C119.7C15W—C16W—C11W120.0
C14C—C15C—H15C119.7C15W—C16W—H16W120.0
C15C—C16C—C11C120.5 (7)C11W—C16W—H16W120.0
C15C—C16C—H16C119.7C22W—C21W—C26W120.0
C11C—C16C—H16C119.7C22W—C21W—C1W127 (3)
C22C—C21C—C26C119.7 (5)C26W—C21W—C1W113 (3)
C22C—C21C—N1C117.8 (5)F22W—C22W—C21W125 (3)
C26C—C21C—N1C122.3 (6)F22W—C22W—C23W114 (3)
N23C—C22C—C21C125.0 (5)C21W—C22W—C23W120.0
N23C—C22C—H22C117.5C22W—C23W—C24W120.0
C21C—C22C—H22C117.5C22W—C23W—H23W120.0
C22C—N23C—C24C114.9 (6)C24W—C23W—H23W120.0
C25C—C24C—N23C123.0 (5)C25W—C24W—C23W120.0
C25C—C24C—H24C118.5C25W—C24W—H24W120.0
N23C—C24C—H24C118.5C23W—C24W—H24W120.0
C24C—C25C—C26C122.6 (6)C24W—C25W—C26W120.0
C24C—C25C—H25C118.7C24W—C25W—H25W120.0
C26C—C25C—H25C118.7C26W—C25W—H25W120.0
C21C—C26C—C25C114.7 (7)C25W—C26W—C21W120.0
C21C—C26C—H26C122.7C25W—C26W—H26W120.0
C25C—C26C—H26C122.7C21W—C26W—H26W120.0
O1D—C1D—N1D123.5 (7)O1X—C1X—N1X124 (3)
O1D—C1D—C11D119.5 (7)O1X—C1X—C21X107 (3)
N1D—C1D—C11D117.0 (6)N1X—C1X—C21X129 (3)
C1D—N1D—C21D125.3 (5)C1X—N1X—C11X130 (3)
C1D—N1D—H1D117.3C1X—N1X—H1X114.9
C21D—N1D—H1D117.3C11X—N1X—H1X114.9
C16D—C11D—C12D115.1 (5)N1X—C11X—C12X118 (3)
C16D—C11D—C1D121.0 (6)N1X—C11X—C16X122 (3)
C12D—C11D—C1D123.8 (5)C12X—C11X—C16X120.0
F12D—C12D—C13D118.6 (6)C11X—C12X—N13X120.0
F12D—C12D—C11D119.6 (5)C11X—C12X—H12X120.0
C13D—C12D—C11D121.8 (6)N13X—C12X—H12X120.0
C14D—C13D—C12D121.6 (7)C12X—N13X—C14X120.0
C14D—C13D—H13D119.2C15X—C14X—N13X120.0
C12D—C13D—H13D119.2C15X—C14X—H14X120.0
C13D—C14D—C15D120.2 (6)N13X—C14X—H14X120.0
C13D—C14D—H14D119.9C14X—C15X—C16X120.0
C15D—C14D—H14D119.9C14X—C15X—H15X120.0
C16D—C15D—C14D118.4 (6)C16X—C15X—H15X120.0
C16D—C15D—H15D120.8C15X—C16X—C11X120.0
C14D—C15D—H15D120.8C15X—C16X—H16X120.0
C11D—C16D—C15D122.8 (7)C11X—C16X—H16X120.0
C11D—C16D—H16D118.6C22X—C21X—C26X120.0
C15D—C16D—H16D118.6C22X—C21X—C1X111 (3)
C26D—C21D—N1D127.0 (6)C26X—C21X—C1X128 (3)
C26D—C21D—C22D118.3 (4)C23X—C22X—C21X120.0
N1D—C21D—C22D114.7 (5)C23X—C22X—F22X113 (2)
N23D—C22D—C21D123.7 (5)C21X—C22X—F22X127 (2)
N23D—C22D—H22D118.1C22X—C23X—C24X120.0
C21D—C22D—H22D118.1C22X—C23X—H23X120.0
C22D—N23D—C24D116.6 (6)C24X—C23X—H23X120.0
C25D—C24D—N23D123.8 (5)C25X—C24X—C23X120.0
C25D—C24D—H24D118.1C25X—C24X—H24X120.0
N23D—C24D—H24D118.1C23X—C24X—H24X120.0
C24D—C25D—C26D121.2 (6)C24X—C25X—C26X120.0
C24D—C25D—H25D119.4C24X—C25X—H25X120.0
C26D—C25D—H25D119.4C26X—C25X—H25X120.0
C21D—C26D—C25D116.3 (6)C25X—C26X—C21X120.0
C21D—C26D—H26D121.8C25X—C26X—H26X120.0
C25D—C26D—H26D121.8C21X—C26X—H26X120.0
O1E—C1E—N1E123 (2)O1Y—C1Y—N1Y113 (2)
O1E—C1E—C11E125 (2)O1Y—C1Y—C21Y129 (3)
N1E—C1E—C11E111.6 (12)N1Y—C1Y—C21Y111.7 (19)
C1E—N1E—C21E127.7 (10)C1Y—N1Y—C11Y109.4 (19)
C1E—N1E—H1E116.2C1Y—N1Y—H1Y125.3
C21E—N1E—H1E116.2C11Y—N1Y—H1Y125.3
C12E—C11E—C16E112.5 (15)C12Y—C11Y—C16Y120.0
C12E—C11E—C1E129.5 (14)C12Y—C11Y—N1Y102.8 (16)
C16E—C11E—C1E116.7 (16)C16Y—C11Y—N1Y125.2 (19)
C11E—C12E—F12E120.6 (10)C11Y—C12Y—N13Y120.0
C11E—C12E—C13E126.7 (17)C11Y—C12Y—H12Y120.0
F12E—C12E—C13E112.7 (16)N13Y—C12Y—H12Y120.0
C14E—C13E—C12E119 (2)C14Y—N13Y—C12Y120.0
C14E—C13E—H13E120.6N13Y—C14Y—C15Y120.0
C12E—C13E—H13E120.6N13Y—C14Y—H14Y120.0
C15E—C14E—C13E118 (2)C15Y—C14Y—H14Y120.0
C15E—C14E—H14E121.2C16Y—C15Y—C14Y120.0
C13E—C14E—H14E121.2C16Y—C15Y—H15Y120.0
C14E—C15E—C16E119 (3)C14Y—C15Y—H15Y120.0
C14E—C15E—H15E120.6C15Y—C16Y—C11Y120.0
C16E—C15E—H15E120.6C15Y—C16Y—H16Y120.0
C11E—C16E—C15E124 (3)C11Y—C16Y—H16Y120.0
C11E—C16E—H16E117.9C22Y—C21Y—C26Y120.0
C15E—C16E—H16E117.9C22Y—C21Y—C1Y131.1 (18)
C22E—C21E—N1E116.7 (11)C26Y—C21Y—C1Y108.7 (18)
C22E—C21E—C26E115.8 (12)F22Y—C22Y—C23Y123.3 (17)
N1E—C21E—C26E127.3 (13)F22Y—C22Y—C21Y116.5 (16)
C21E—C22E—N23E125.2 (12)C23Y—C22Y—C21Y120.0
C21E—C22E—H22E117.4C22Y—C23Y—C24Y120.0
N23E—C22E—H22E117.4C22Y—C23Y—H23Y120.0
C24E—N23E—C22E117.6 (14)C24Y—C23Y—H23Y120.0
N23E—C24E—C25E120 (2)C25Y—C24Y—C23Y120.0
N23E—C24E—H24E120.2C25Y—C24Y—H24Y120.0
C25E—C24E—H24E120.2C23Y—C24Y—H24Y120.0
C26E—C25E—C24E124 (3)C24Y—C25Y—C26Y120.0
C26E—C25E—H25E117.8C24Y—C25Y—H25Y120.0
C24E—C25E—H25E117.8C26Y—C25Y—H25Y120.0
C25E—C26E—C21E116 (2)C25Y—C26Y—C21Y120.0
C25E—C26E—H26E121.9C25Y—C26Y—H26Y120.0
C21E—C26E—H26E121.9C21Y—C26Y—H26Y120.0
O1G—C1G—N1G126 (3)O1Z—C1Z—N1Z123 (3)
O1G—C1G—C11G120 (3)O1Z—C1Z—C21Z110 (5)
N1G—C1G—C11G113.6 (13)N1Z—C1Z—C21Z127 (5)
C1G—N1G—C21G126.4 (13)C1Z—N1Z—C11Z129 (3)
C1G—N1G—H1G116.8C1Z—N1Z—H1Z115.4
C21G—N1G—H1G116.8C11Z—N1Z—H1Z115.4
C16G—C11G—C12G114.7 (16)N1Z—C11Z—C12Z115 (3)
C16G—C11G—C1G115.3 (18)N1Z—C11Z—C16Z124 (3)
C12G—C11G—C1G129.8 (15)C12Z—C11Z—C16Z120.0
C11G—C12G—F12G119.2 (11)N13Z—C12Z—C11Z120.0
C11G—C12G—C13G128.9 (14)N13Z—C12Z—H12Z120.0
F12G—C12G—C13G111.7 (14)C11Z—C12Z—H12Z120.0
C12G—C13G—C14G110.8 (16)C12Z—N13Z—C14Z120.0
C12G—C13G—H13G124.6C15Z—C14Z—N13Z120.0
C14G—C13G—H13G124.6C15Z—C14Z—H14Z120.0
C15G—C14G—C13G124 (2)N13Z—C14Z—H14Z120.0
C15G—C14G—H14G117.8C16Z—C15Z—C14Z120.0
C13G—C14G—H14G117.8C16Z—C15Z—H15Z120.0
C14G—C15G—C16G114 (3)C14Z—C15Z—H15Z120.0
C14G—C15G—H15G123.1C15Z—C16Z—C11Z120.0
C16G—C15G—H15G123.1C15Z—C16Z—H16Z120.0
C11G—C16G—C15G126 (3)C11Z—C16Z—H16Z120.0
C11G—C16G—H16G116.9C22Z—C21Z—C26Z120.0
C15G—C16G—H16G116.9C22Z—C21Z—C1Z112 (7)
C22G—C21G—N1G116.3 (17)C26Z—C21Z—C1Z127 (7)
C22G—C21G—C26G124.8 (16)C21Z—C22Z—C23Z120.0
N1G—C21G—C26G118.9 (19)C21Z—C22Z—F22Z131 (7)
N23G—C22G—C21G126.9 (15)C23Z—C22Z—F22Z108 (7)
N23G—C22G—H22G116.5C24Z—C23Z—C22Z120.0
C21G—C22G—H22G116.5C24Z—C23Z—H23Z120.0
C22G—N23G—C24G108.3 (19)C22Z—C23Z—H23Z120.0
C25G—C24G—N23G125 (3)C23Z—C24Z—C25Z120.0
C25G—C24G—H24G117.7C23Z—C24Z—H24Z120.0
N23G—C24G—H24G117.7C25Z—C24Z—H24Z120.0
C24G—C25G—C26G129 (4)C26Z—C25Z—C24Z120.0
C24G—C25G—H25G115.4C26Z—C25Z—H25Z120.0
C26G—C25G—H25G115.4C24Z—C25Z—H25Z120.0
C25G—C26G—C21G106 (3)C25Z—C26Z—C21Z120.0
C25G—C26G—H26G127.1C25Z—C26Z—H26Z120.0
C21G—C26G—H26G127.1C21Z—C26Z—H26Z120.0
O1A—C1A—N1A—C21A7.1 (10)O1F—C1F—N1F—C21F10 (4)
C11A—C1A—N1A—C21A173.6 (5)C11F—C1F—N1F—C21F179.5 (15)
O1A—C1A—C11A—C12A147.7 (7)O1F—C1F—C11F—C16F27 (4)
N1A—C1A—C11A—C12A33.1 (9)N1F—C1F—C11F—C16F144 (2)
O1A—C1A—C11A—C16A24.7 (9)O1F—C1F—C11F—C12F157 (2)
N1A—C1A—C11A—C16A154.5 (6)N1F—C1F—C11F—C12F32 (3)
C16A—C11A—C12A—C13A5.3 (9)C16F—C11F—C12F—F12F176 (2)
C1A—C11A—C12A—C13A177.5 (6)C1F—C11F—C12F—F12F0 (2)
C16A—C11A—C12A—F12A173.5 (5)C16F—C11F—C12F—C13F6 (3)
C1A—C11A—C12A—F12A1.3 (9)C1F—C11F—C12F—C13F178.3 (16)
C11A—C12A—C13A—C14A0.5 (9)F12F—C12F—C13F—C14F179 (2)
F12A—C12A—C13A—C14A178.4 (6)C11F—C12F—C13F—C14F1 (3)
C12A—C13A—C14A—C15A2.9 (10)C12F—C13F—C14F—C15F0 (5)
C13A—C14A—C15A—C16A1.1 (12)C13F—C14F—C15F—C16F3 (5)
C14A—C15A—C16A—C11A3.8 (10)C12F—C11F—C16F—C15F10 (5)
C12A—C11A—C16A—C15A6.7 (8)C1F—C11F—C16F—C15F173 (3)
C1A—C11A—C16A—C15A179.9 (6)C14F—C15F—C16F—C11F9 (5)
C1A—N1A—C21A—C22A155.1 (6)C1F—N1F—C21F—C26F154.3 (16)
C1A—N1A—C21A—C26A26.4 (8)C1F—N1F—C21F—C22F22 (2)
N1A—C21A—C22A—N23A179.6 (5)N1F—C21F—C22F—N23F178.0 (14)
C26A—C21A—C22A—N23A1.1 (8)C26F—C21F—C22F—N23F2 (2)
C21A—C22A—N23A—C24A1.2 (9)C21F—C22F—N23F—C24F2 (4)
C22A—N23A—C24A—C25A1.0 (9)C22F—N23F—C24F—C25F3 (5)
N23A—C24A—C25A—C26A0.8 (10)N23F—C24F—C25F—C26F0 (3)
C24A—C25A—C26A—C21A0.6 (9)C24F—C25F—C26F—C21F4 (3)
C22A—C21A—C26A—C25A0.7 (8)N1F—C21F—C26F—C25F178.9 (13)
N1A—C21A—C26A—C25A179.2 (5)C22F—C21F—C26F—C25F5 (2)
O1B—C1B—N1B—C21B8.3 (11)O1H—C1H—N1H—C21H1 (4)
C11B—C1B—N1B—C21B174.9 (5)C11H—C1H—N1H—C21H171.7 (15)
O1B—C1B—C11B—C16B22.6 (11)O1H—C1H—C11H—C16H39 (5)
N1B—C1B—C11B—C16B154.3 (6)N1H—C1H—C11H—C16H148 (3)
O1B—C1B—C11B—C12B151.7 (8)O1H—C1H—C11H—C12H146 (3)
N1B—C1B—C11B—C12B31.4 (9)N1H—C1H—C11H—C12H26 (3)
C16B—C11B—C12B—F12B177.0 (5)C16H—C11H—C12H—C13H6 (2)
C1B—C11B—C12B—F12B2.5 (8)C1H—C11H—C12H—C13H178.3 (18)
C16B—C11B—C12B—C13B3.4 (8)C16H—C11H—C12H—F12H177.7 (19)
C1B—C11B—C12B—C13B177.9 (6)C1H—C11H—C12H—F12H2 (2)
F12B—C12B—C13B—C14B178.1 (6)F12H—C12H—C13H—C14H174.2 (17)
C11B—C12B—C13B—C14B2.3 (9)C11H—C12H—C13H—C14H2 (2)
C12B—C13B—C14B—C15B1.3 (10)C12H—C13H—C14H—C15H3 (3)
C13B—C14B—C15B—C16B3.7 (10)C13H—C14H—C15H—C16H3 (3)
C12B—C11B—C16B—C15B1.0 (8)C12H—C11H—C16H—C15H24 (7)
C1B—C11B—C16B—C15B175.7 (6)C1H—C11H—C16H—C15H160 (5)
C14B—C15B—C16B—C11B2.4 (10)C14H—C15H—C16H—C11H23 (7)
C1B—N1B—C21B—C26B29.4 (9)C1H—N1H—C21H—C26H158 (2)
C1B—N1B—C21B—C22B155.7 (6)C1H—N1H—C21H—C22H25 (3)
C26B—C21B—C22B—N23B5.1 (9)C26H—C21H—C22H—N23H4 (5)
N1B—C21B—C22B—N23B179.5 (5)N1H—C21H—C22H—N23H180 (3)
C21B—C22B—N23B—C24B3.0 (9)C21H—C22H—N23H—C24H4 (5)
C22B—N23B—C24B—C25B1.2 (10)C22H—N23H—C24H—C25H0 (5)
N23B—C24B—C25B—C26B1.7 (10)N23H—C24H—C25H—C26H3 (3)
C22B—C21B—C26B—C25B5.4 (9)C24H—C25H—C26H—C21H3 (3)
N1B—C21B—C26B—C25B179.8 (6)N1H—C21H—C26H—C25H176.9 (13)
C24B—C25B—C26B—C21B3.8 (10)C22H—C21H—C26H—C25H0 (3)
O1C—C1C—N1C—C21C10.8 (10)O1W—C1W—N1W—C11W20 (10)
C11C—C1C—N1C—C21C174.2 (5)C21W—C1W—N1W—C11W171 (4)
O1C—C1C—C11C—C12C154.4 (9)C1W—N1W—C11W—C12W140 (5)
N1C—C1C—C11C—C12C30.6 (10)C1W—N1W—C11W—C16W37 (7)
O1C—C1C—C11C—C16C19.0 (10)N1W—C11W—C12W—N13W177 (4)
N1C—C1C—C11C—C16C156.0 (7)C16W—C11W—C12W—N13W0.0
C16C—C11C—C12C—F12C170.7 (8)C11W—C12W—N13W—C14W0.0
C1C—C11C—C12C—F12C2.8 (12)C12W—N13W—C14W—C15W0.0
C16C—C11C—C12C—C13C1.6 (12)N13W—C14W—C15W—C16W0.0
C1C—C11C—C12C—C13C175.0 (9)C14W—C15W—C16W—C11W0.0
C11C—C12C—C13C—C14C2.4 (13)N1W—C11W—C16W—C15W176 (5)
F12C—C12C—C13C—C14C170.3 (9)C12W—C11W—C16W—C15W0.0
C12C—C13C—C14C—C15C2.7 (11)O1W—C1W—C21W—C22W162 (7)
C13C—C14C—C15C—C16C2.4 (11)N1W—C1W—C21W—C22W31 (7)
C14C—C15C—C16C—C11C1.5 (10)O1W—C1W—C21W—C26W26 (10)
C12C—C11C—C16C—C15C1.1 (10)N1W—C1W—C21W—C26W141 (5)
C1C—C11C—C16C—C15C175.3 (8)C26W—C21W—C22W—F22W176 (4)
C1C—N1C—C21C—C22C151.6 (6)C1W—C21W—C22W—F22W3 (5)
C1C—N1C—C21C—C26C22.8 (10)C26W—C21W—C22W—C23W0.0
C26C—C21C—C22C—N23C5.3 (11)C1W—C21W—C22W—C23W172 (4)
N1C—C21C—C22C—N23C179.8 (6)F22W—C22W—C23W—C24W176 (4)
C21C—C22C—N23C—C24C4.0 (11)C21W—C22W—C23W—C24W0.0
C22C—N23C—C24C—C25C2.3 (14)C22W—C23W—C24W—C25W0.0
N23C—C24C—C25C—C26C2.0 (16)C23W—C24W—C25W—C26W0.0
C22C—C21C—C26C—C25C4.3 (10)C24W—C25W—C26W—C21W0.0
N1C—C21C—C26C—C25C178.6 (6)C22W—C21W—C26W—C25W0.0
C24C—C25C—C26C—C21C2.9 (12)C1W—C21W—C26W—C25W173 (4)
O1D—C1D—N1D—C21D6.6 (10)O1X—C1X—N1X—C11X4 (11)
C11D—C1D—N1D—C21D175.1 (5)C21X—C1X—N1X—C11X177 (4)
O1D—C1D—C11D—C16D34.1 (10)C1X—N1X—C11X—C12X151 (5)
N1D—C1D—C11D—C16D144.3 (6)C1X—N1X—C11X—C16X28 (6)
O1D—C1D—C11D—C12D150.3 (7)N1X—C11X—C12X—N13X179 (3)
N1D—C1D—C11D—C12D31.3 (8)C16X—C11X—C12X—N13X0.0
C16D—C11D—C12D—F12D177.9 (6)C11X—C12X—N13X—C14X0.0
C1D—C11D—C12D—F12D2.0 (8)C12X—N13X—C14X—C15X0.0
C16D—C11D—C12D—C13D3.4 (8)N13X—C14X—C15X—C16X0.0
C1D—C11D—C12D—C13D179.2 (6)C14X—C15X—C16X—C11X0.0
F12D—C12D—C13D—C14D179.3 (6)N1X—C11X—C16X—C15X179 (3)
C11D—C12D—C13D—C14D0.6 (9)C12X—C11X—C16X—C15X0.0
C12D—C13D—C14D—C15D1.4 (10)O1X—C1X—C21X—C22X153 (5)
C13D—C14D—C15D—C16D0.5 (11)N1X—C1X—C21X—C22X27 (8)
C12D—C11D—C16D—C15D4.3 (10)O1X—C1X—C21X—C26X34 (8)
C1D—C11D—C16D—C15D179.7 (7)N1X—C1X—C21X—C26X146 (5)
C14D—C15D—C16D—C11D2.5 (11)C26X—C21X—C22X—C23X0.0
C1D—N1D—C21D—C26D27.8 (8)C1X—C21X—C22X—C23X174 (4)
C1D—N1D—C21D—C22D154.0 (5)C26X—C21X—C22X—F22X176 (4)
C26D—C21D—C22D—N23D0.8 (8)C1X—C21X—C22X—F22X2 (4)
N1D—C21D—C22D—N23D179.2 (5)C21X—C22X—C23X—C24X0.0
C21D—C22D—N23D—C24D1.3 (8)F22X—C22X—C23X—C24X176 (3)
C22D—N23D—C24D—C25D2.8 (9)C22X—C23X—C24X—C25X0.0
N23D—C24D—C25D—C26D2.3 (10)C23X—C24X—C25X—C26X0.0
N1D—C21D—C26D—C25D179.5 (5)C24X—C25X—C26X—C21X0.0
C22D—C21D—C26D—C25D1.4 (8)C22X—C21X—C26X—C25X0.0
C24D—C25D—C26D—C21D0.1 (8)C1X—C21X—C26X—C25X173 (5)
O1E—C1E—N1E—C21E11 (4)O1Y—C1Y—N1Y—C11Y3 (4)
C11E—C1E—N1E—C21E173.7 (13)C21Y—C1Y—N1Y—C11Y153 (2)
O1E—C1E—C11E—C12E150 (3)C1Y—N1Y—C11Y—C12Y148 (2)
N1E—C1E—C11E—C12E35 (2)C1Y—N1Y—C11Y—C16Y70 (3)
O1E—C1E—C11E—C16E16 (4)C16Y—C11Y—C12Y—N13Y0.0
N1E—C1E—C11E—C16E159.1 (14)N1Y—C11Y—C12Y—N13Y144 (2)
C16E—C11E—C12E—F12E168.6 (13)C11Y—C12Y—N13Y—C14Y0.0
C1E—C11E—C12E—F12E2 (2)C12Y—N13Y—C14Y—C15Y0.0
C16E—C11E—C12E—C13E11 (2)N13Y—C14Y—C15Y—C16Y0.0
C1E—C11E—C12E—C13E177.3 (19)C14Y—C15Y—C16Y—C11Y0.0
C11E—C12E—C13E—C14E2 (3)C12Y—C11Y—C16Y—C15Y0.0
F12E—C12E—C13E—C14E178 (2)N1Y—C11Y—C16Y—C15Y136 (3)
C12E—C13E—C14E—C15E6 (4)O1Y—C1Y—C21Y—C22Y106 (3)
C13E—C14E—C15E—C16E4 (5)N1Y—C1Y—C21Y—C22Y45 (4)
C12E—C11E—C16E—C15E13 (3)O1Y—C1Y—C21Y—C26Y68 (4)
C1E—C11E—C16E—C15E179 (2)N1Y—C1Y—C21Y—C26Y141 (2)
C14E—C15E—C16E—C11E6 (4)C26Y—C21Y—C22Y—F22Y176 (2)
C1E—N1E—C21E—C22E153.9 (14)C1Y—C21Y—C22Y—F22Y11 (3)
C1E—N1E—C21E—C26E22 (2)C26Y—C21Y—C22Y—C23Y0.0
N1E—C21E—C22E—N23E178.7 (12)C1Y—C21Y—C22Y—C23Y174 (3)
C26E—C21E—C22E—N23E5 (2)F22Y—C22Y—C23Y—C24Y175 (3)
C21E—C22E—N23E—C24E3 (2)C21Y—C22Y—C23Y—C24Y0.0
C22E—N23E—C24E—C25E5 (3)C22Y—C23Y—C24Y—C25Y0.0
N23E—C24E—C25E—C26E11 (4)C23Y—C24Y—C25Y—C26Y0.0
C24E—C25E—C26E—C21E12 (4)C24Y—C25Y—C26Y—C21Y0.0
C22E—C21E—C26E—C25E9 (3)C22Y—C21Y—C26Y—C25Y0.0
N1E—C21E—C26E—C25E175 (2)C1Y—C21Y—C26Y—C25Y175 (2)
O1G—C1G—N1G—C21G1 (4)O1Z—C1Z—N1Z—C11Z5 (8)
C11G—C1G—N1G—C21G174.0 (15)C21Z—C1Z—N1Z—C11Z168 (5)
O1G—C1G—C11G—C16G38 (4)C1Z—N1Z—C11Z—C12Z175 (4)
N1G—C1G—C11G—C16G149 (2)C1Z—N1Z—C11Z—C16Z13 (6)
O1G—C1G—C11G—C12G148 (3)N1Z—C11Z—C12Z—N13Z172 (3)
N1G—C1G—C11G—C12G25 (2)C16Z—C11Z—C12Z—N13Z0.0
C16G—C11G—C12G—F12G179.6 (18)C11Z—C12Z—N13Z—C14Z0.0
C1G—C11G—C12G—F12G5 (2)C12Z—N13Z—C14Z—C15Z0.0
C16G—C11G—C12G—C13G5 (3)N13Z—C14Z—C15Z—C16Z0.0
C1G—C11G—C12G—C13G180.0 (15)C14Z—C15Z—C16Z—C11Z0.0
C11G—C12G—C13G—C14G3 (2)N1Z—C11Z—C16Z—C15Z172 (4)
F12G—C12G—C13G—C14G177.9 (14)C12Z—C11Z—C16Z—C15Z0.0
C12G—C13G—C14G—C15G5 (3)O1Z—C1Z—C21Z—C22Z144 (5)
C13G—C14G—C15G—C16G9 (4)N1Z—C1Z—C21Z—C22Z29 (8)
C12G—C11G—C16G—C15G10 (4)O1Z—C1Z—C21Z—C26Z26 (8)
C1G—C11G—C16G—C15G175 (2)N1Z—C1Z—C21Z—C26Z161 (5)
C14G—C15G—C16G—C11G12 (4)C26Z—C21Z—C22Z—C23Z0.0
C1G—N1G—C21G—C22G148.5 (15)C1Z—C21Z—C22Z—C23Z171 (7)
C1G—N1G—C21G—C26G30 (2)C26Z—C21Z—C22Z—F22Z169 (7)
N1G—C21G—C22G—N23G177.8 (17)C1Z—C21Z—C22Z—F22Z20 (7)
C26G—C21G—C22G—N23G4 (3)C21Z—C22Z—C23Z—C24Z0.0
C21G—C22G—N23G—C24G5 (3)F22Z—C22Z—C23Z—C24Z171 (6)
C22G—N23G—C24G—C25G6 (4)C22Z—C23Z—C24Z—C25Z0.0
N23G—C24G—C25G—C26G5 (6)C23Z—C24Z—C25Z—C26Z0.0
C24G—C25G—C26G—C21G3 (5)C24Z—C25Z—C26Z—C21Z0.0
C22G—C21G—C26G—C25G2 (3)C22Z—C21Z—C26Z—C25Z0.0
N1G—C21G—C26G—C25G180 (2)C1Z—C21Z—C26Z—C25Z169 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1Ai0.862.323.117 (8)154
N1B—H1B···O1Bii0.862.313.099 (10)153
N1C—H1C···O1Ci0.862.293.074 (8)152
N1D—H1D···O1Dii0.862.293.093 (9)157
N1E—H1E···O1Ei0.862.353.15 (3)155
N1G—H1G···O1Gi0.862.253.05 (3)155
N1F—H1F···O1Fii0.862.363.15 (2)153
N1H—H1H···O1Hii0.862.293.08 (3)153
N1A—H1A···F12A0.862.262.766 (5)118
N1B—H1B···F12B0.862.192.720 (5)119
N1C—H1C···F12C0.862.202.727 (5)119
N1D—H1D···F12D0.862.222.723 (5)117
N1E—H1E···F12E0.862.262.773 (9)118
N1F—H1F···F12F0.862.162.698 (9)120
N1G—H1G···F12G0.862.182.727 (11)122
N1H—H1H···F12H0.862.192.720 (10)120
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.
(Fom_F-11-061) 2-Fluoro-N-(pyridin-3-yl)benzamide top
Crystal data top
C12H9FN2OF(000) = 448
Mr = 216.21Dx = 1.455 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1933 reflections
a = 5.4788 (2) Åθ = 2.6–27.5°
b = 8.8223 (4) ŵ = 0.11 mm1
c = 20.4414 (7) ÅT = 294 K
β = 92.150 (4)°Block, colourless
V = 987.35 (7) Å30.49 × 0.25 × 0.12 mm
Z = 4
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
1599 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.027
Graphite monochromatorθmax = 27.8°, θmin = 2.5°
ω scansh = 76
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
k = 1111
Tmin = 0.949, Tmax = 0.987l = 2525
7439 measured reflections7692 standard reflections every 60 min
2178 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0574P)2 + 0.0509P]
where P = (Fo2 + 2Fc2)/3
2178 reflections(Δ/σ)max < 0.001
149 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C12H9FN2OV = 987.35 (7) Å3
Mr = 216.21Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.4788 (2) ŵ = 0.11 mm1
b = 8.8223 (4) ÅT = 294 K
c = 20.4414 (7) Å0.49 × 0.25 × 0.12 mm
β = 92.150 (4)°
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
1599 reflections with I > 2σ(I)
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
Rint = 0.027
Tmin = 0.949, Tmax = 0.9877692 standard reflections every 60 min
7439 measured reflections intensity decay: 1%
2178 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.14 e Å3
2178 reflectionsΔρmin = 0.18 e Å3
149 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
F120.30000 (17)0.14212 (11)0.03176 (4)0.0653 (3)
O10.32635 (19)0.19644 (13)0.08572 (5)0.0603 (3)
C10.1209 (3)0.19535 (16)0.06046 (7)0.0463 (4)
N10.0737 (3)0.13310 (14)0.08955 (7)0.0503 (4)
H10.208 (3)0.1374 (18)0.0676 (8)0.058 (5)*
C110.0713 (3)0.26922 (15)0.00498 (7)0.0427 (3)
C120.1275 (3)0.24621 (17)0.04718 (7)0.0472 (4)
C130.1620 (3)0.32263 (19)0.10533 (8)0.0548 (4)
H130.29960.30420.13220.066*
C140.0096 (3)0.4266 (2)0.12322 (8)0.0570 (4)
H140.01220.48050.16210.068*
C150.2136 (3)0.45069 (18)0.08343 (8)0.0575 (4)
H150.33200.51950.09580.069*
C160.2427 (3)0.37304 (17)0.02537 (8)0.0518 (4)
H160.38170.39060.00110.062*
C210.0725 (3)0.04988 (16)0.14850 (7)0.0448 (4)
C220.1128 (3)0.0553 (2)0.19618 (8)0.0642 (5)
H220.24430.11960.19000.077*
N230.1115 (3)0.0280 (2)0.25101 (7)0.0728 (5)
C240.0789 (3)0.1161 (2)0.25990 (8)0.0607 (5)
H240.08120.17430.29780.073*
C250.2730 (3)0.1262 (2)0.21610 (9)0.0619 (5)
H250.40520.18850.22440.074*
C260.2687 (3)0.04226 (18)0.15959 (8)0.0562 (4)
H260.39810.04780.12890.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F120.0575 (6)0.0760 (7)0.0613 (6)0.0182 (5)0.0111 (5)0.0005 (5)
O10.0467 (7)0.0713 (8)0.0617 (7)0.0041 (5)0.0136 (5)0.0125 (6)
C10.0480 (9)0.0390 (8)0.0512 (9)0.0016 (6)0.0065 (7)0.0014 (6)
N10.0441 (8)0.0541 (8)0.0519 (8)0.0023 (6)0.0090 (6)0.0082 (6)
C110.0441 (8)0.0380 (7)0.0456 (8)0.0045 (6)0.0050 (6)0.0037 (6)
C120.0436 (8)0.0482 (8)0.0498 (9)0.0002 (6)0.0001 (7)0.0073 (7)
C130.0522 (9)0.0662 (10)0.0452 (9)0.0059 (8)0.0091 (7)0.0057 (8)
C140.0628 (11)0.0610 (10)0.0469 (9)0.0079 (8)0.0016 (8)0.0062 (7)
C150.0586 (10)0.0544 (10)0.0590 (10)0.0028 (8)0.0020 (8)0.0076 (8)
C160.0484 (9)0.0502 (9)0.0561 (10)0.0010 (7)0.0097 (7)0.0016 (7)
C210.0470 (8)0.0441 (8)0.0431 (8)0.0042 (6)0.0028 (6)0.0018 (6)
C220.0587 (10)0.0826 (13)0.0507 (10)0.0164 (9)0.0084 (8)0.0032 (9)
N230.0631 (10)0.1060 (13)0.0482 (8)0.0059 (9)0.0103 (7)0.0074 (8)
C240.0638 (11)0.0699 (11)0.0488 (10)0.0117 (9)0.0060 (8)0.0079 (8)
C250.0597 (11)0.0662 (11)0.0597 (11)0.0073 (8)0.0006 (9)0.0098 (8)
C260.0503 (10)0.0621 (10)0.0553 (10)0.0054 (8)0.0105 (8)0.0054 (8)
Geometric parameters (Å, º) top
F12—C121.3634 (17)C15—C161.375 (2)
O1—C11.2207 (17)C15—H150.9300
C1—N11.356 (2)C16—H160.9300
C1—C111.5035 (19)C21—C261.373 (2)
N1—C211.4109 (19)C21—C221.382 (2)
N1—H10.850 (17)C22—N231.340 (2)
C11—C121.3787 (19)C22—H220.9300
C11—C161.387 (2)N23—C241.319 (2)
C12—C131.373 (2)C24—C251.367 (2)
C13—C141.373 (2)C24—H240.9300
C13—H130.9300C25—C261.373 (2)
C14—C151.374 (2)C25—H250.9300
C14—H140.9300C26—H260.9300
O1—C1—N1123.05 (14)C16—C15—H15120.0
O1—C1—C11120.40 (14)C15—C16—C11122.05 (15)
N1—C1—C11116.53 (13)C15—C16—H16119.0
C1—N1—C21127.35 (14)C11—C16—H16119.0
C1—N1—H1115.6 (12)C26—C21—C22117.57 (14)
C21—N1—H1116.7 (12)C26—C21—N1118.07 (13)
C12—C11—C16115.91 (14)C22—C21—N1124.36 (14)
C12—C11—C1127.23 (14)N23—C22—C21122.98 (16)
C16—C11—C1116.85 (13)N23—C22—H22118.5
F12—C12—C13117.17 (13)C21—C22—H22118.5
F12—C12—C11119.51 (13)C24—N23—C22117.86 (15)
C13—C12—C11123.31 (15)N23—C24—C25123.21 (16)
C14—C13—C12119.01 (15)N23—C24—H24118.4
C14—C13—H13120.5C25—C24—H24118.4
C12—C13—H13120.5C24—C25—C26118.57 (16)
C13—C14—C15119.72 (15)C24—C25—H25120.7
C13—C14—H14120.1C26—C25—H25120.7
C15—C14—H14120.1C21—C26—C25119.78 (15)
C14—C15—C16119.96 (16)C21—C26—H26120.1
C14—C15—H15120.0C25—C26—H26120.1
O1—C1—N1—C216.1 (2)C14—C15—C16—C110.1 (3)
C11—C1—N1—C21175.78 (12)C12—C11—C16—C151.4 (2)
O1—C1—C11—C12162.20 (15)C1—C11—C16—C15178.19 (13)
N1—C1—C11—C1219.6 (2)C1—N1—C21—C26160.11 (15)
O1—C1—C11—C1618.3 (2)C1—N1—C21—C2220.2 (2)
N1—C1—C11—C16159.90 (13)C26—C21—C22—N232.0 (3)
C16—C11—C12—F12177.76 (13)N1—C21—C22—N23178.34 (16)
C1—C11—C12—F122.7 (2)C21—C22—N23—C241.5 (3)
C16—C11—C12—C131.7 (2)C22—N23—C24—C250.0 (3)
C1—C11—C12—C13177.81 (14)N23—C24—C25—C261.0 (3)
F12—C12—C13—C14178.93 (14)C22—C21—C26—C250.9 (2)
C11—C12—C13—C140.5 (2)N1—C21—C26—C25179.36 (14)
C12—C13—C14—C151.0 (2)C24—C25—C26—C210.5 (3)
C13—C14—C15—C161.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···F120.850 (17)2.074 (17)2.7315 (16)133.7 (15)
C16—H16···O10.932.462.7777 (19)100
C22—H22···O10.932.302.867 (2)119
(Fpo-10-123) 4-Fluoro-N-(pyridin-2-yl)benzamide top
Crystal data top
C12H9FN2ODx = 1.367 Mg m3
Mr = 216.21Melting point: 393 K
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 5919 reflections
a = 24.3381 (4) Åθ = 2.6–27.5°
b = 7.9334 (1) ŵ = 0.10 mm1
c = 10.8791 (2) ÅT = 294 K
V = 2100.58 (6) Å3Block, colourless
Z = 80.58 × 0.53 × 0.17 mm
F(000) = 896
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
1829 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.024
Graphite monochromatorθmax = 27.1°, θmin = 2.7°
ω scansh = 3131
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
k = 109
Tmin = 0.943, Tmax = 0.983l = 1313
14121 measured reflections15398 standard reflections every 60 min
2254 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0441P)2 + 0.4556P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2254 reflectionsΔρmax = 0.14 e Å3
150 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0049 (9)
Crystal data top
C12H9FN2OV = 2100.58 (6) Å3
Mr = 216.21Z = 8
Orthorhombic, PbcnMo Kα radiation
a = 24.3381 (4) ŵ = 0.10 mm1
b = 7.9334 (1) ÅT = 294 K
c = 10.8791 (2) Å0.58 × 0.53 × 0.17 mm
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
1829 reflections with I > 2σ(I)
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
Rint = 0.024
Tmin = 0.943, Tmax = 0.98315398 standard reflections every 60 min
14121 measured reflections intensity decay: 1%
2254 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.14 e Å3
2254 reflectionsΔρmin = 0.17 e Å3
150 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
F140.27947 (5)0.58098 (19)0.21424 (13)0.1205 (5)
O10.08690 (5)0.6898 (2)0.58413 (10)0.0894 (4)
C10.08502 (6)0.6907 (2)0.47221 (13)0.0601 (4)
N10.03851 (5)0.72299 (17)0.40676 (11)0.0573 (3)
H10.0422 (6)0.736 (2)0.3266 (16)0.063 (4)*
C110.13551 (6)0.65978 (19)0.39852 (13)0.0557 (4)
C120.18466 (6)0.7247 (2)0.44292 (16)0.0666 (4)
H120.18480.78560.51600.080*
C130.23289 (7)0.7003 (2)0.38051 (19)0.0777 (5)
H130.26570.74590.40930.093*
C140.23163 (7)0.6080 (3)0.27551 (18)0.0787 (5)
C150.18440 (8)0.5402 (3)0.22916 (17)0.0799 (5)
H150.18500.47710.15710.096*
C160.13576 (6)0.5673 (2)0.29161 (14)0.0654 (4)
H160.10310.52290.26130.078*
C210.01308 (6)0.76908 (18)0.45356 (13)0.0547 (4)
N220.04904 (5)0.80967 (17)0.36639 (11)0.0615 (3)
C230.09843 (6)0.8627 (2)0.40284 (17)0.0705 (4)
H230.12370.89380.34290.085*
C240.11413 (7)0.8739 (2)0.52355 (17)0.0748 (5)
H240.14890.91270.54510.090*
C250.07721 (8)0.8265 (3)0.61095 (17)0.0841 (6)
H250.08690.82990.69360.101*
C260.02586 (7)0.7736 (3)0.57699 (15)0.0761 (5)
H260.00020.74160.63580.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F140.0807 (7)0.1531 (13)0.1277 (10)0.0294 (7)0.0413 (7)0.0364 (9)
O10.0833 (8)0.1400 (12)0.0451 (6)0.0210 (8)0.0079 (5)0.0041 (7)
C10.0608 (9)0.0726 (9)0.0470 (8)0.0018 (7)0.0076 (6)0.0009 (7)
N10.0513 (7)0.0803 (9)0.0404 (6)0.0009 (6)0.0009 (5)0.0009 (6)
C110.0542 (8)0.0633 (8)0.0497 (7)0.0029 (6)0.0072 (6)0.0042 (6)
C120.0639 (9)0.0702 (10)0.0657 (9)0.0011 (7)0.0161 (7)0.0016 (8)
C130.0550 (9)0.0816 (12)0.0964 (14)0.0017 (8)0.0083 (9)0.0185 (11)
C140.0613 (10)0.0916 (13)0.0833 (12)0.0169 (9)0.0153 (9)0.0275 (11)
C150.0821 (12)0.0936 (13)0.0638 (10)0.0221 (10)0.0027 (8)0.0036 (9)
C160.0611 (9)0.0755 (10)0.0595 (9)0.0048 (7)0.0082 (7)0.0056 (8)
C210.0534 (8)0.0630 (8)0.0476 (7)0.0059 (6)0.0025 (6)0.0017 (6)
N220.0497 (6)0.0796 (9)0.0553 (7)0.0005 (6)0.0025 (5)0.0022 (6)
C230.0544 (8)0.0799 (11)0.0771 (11)0.0010 (8)0.0050 (8)0.0010 (9)
C240.0634 (10)0.0745 (10)0.0867 (12)0.0003 (8)0.0250 (9)0.0062 (9)
C250.0873 (13)0.1020 (14)0.0631 (10)0.0013 (11)0.0243 (10)0.0030 (10)
C260.0742 (11)0.1038 (14)0.0504 (9)0.0053 (9)0.0081 (8)0.0013 (9)
Geometric parameters (Å, º) top
F14—C141.3585 (19)C15—C161.382 (2)
O1—C11.2185 (18)C15—H150.9300
C1—N11.3616 (18)C16—H160.9300
C1—C111.488 (2)C21—N221.3299 (18)
N1—C211.4034 (18)C21—C261.379 (2)
N1—H10.883 (17)N22—C231.3339 (19)
C11—C161.375 (2)C23—C241.371 (2)
C11—C121.389 (2)C23—H230.9300
C12—C131.370 (2)C24—C251.361 (3)
C12—H120.9300C24—H240.9300
C13—C141.358 (3)C25—C261.369 (2)
C13—H130.9300C25—H250.9300
C14—C151.366 (3)C26—H260.9300
O1—C1—N1123.71 (14)C16—C15—H15120.7
O1—C1—C11120.43 (13)C11—C16—C15120.18 (15)
N1—C1—C11115.84 (12)C11—C16—H16119.9
C1—N1—C21127.09 (12)C15—C16—H16119.9
C1—N1—H1116.9 (10)N22—C21—C26122.66 (14)
C21—N1—H1114.8 (10)N22—C21—N1113.15 (12)
C16—C11—C12119.22 (14)C26—C21—N1124.19 (14)
C16—C11—C1123.20 (13)C21—N22—C23117.21 (13)
C12—C11—C1117.56 (14)N22—C23—C24123.82 (17)
C13—C12—C11120.88 (16)N22—C23—H23118.1
C13—C12—H12119.6C24—C23—H23118.1
C11—C12—H12119.6C25—C24—C23117.86 (16)
C14—C13—C12118.29 (16)C25—C24—H24121.1
C14—C13—H13120.9C23—C24—H24121.1
C12—C13—H13120.9C24—C25—C26119.91 (16)
C13—C14—F14118.60 (18)C24—C25—H25120.0
C13—C14—C15122.84 (16)C26—C25—H25120.0
F14—C14—C15118.56 (19)C25—C26—C21118.47 (17)
C14—C15—C16118.57 (17)C25—C26—H26120.8
C14—C15—H15120.7C21—C26—H26120.8
O1—C1—N1—C213.9 (3)C12—C11—C16—C150.2 (2)
C11—C1—N1—C21174.57 (14)C1—C11—C16—C15178.51 (15)
O1—C1—C11—C16141.45 (17)C14—C15—C16—C110.5 (3)
N1—C1—C11—C1640.0 (2)C1—N1—C21—N22173.24 (15)
O1—C1—C11—C1236.8 (2)C1—N1—C21—C266.4 (3)
N1—C1—C11—C12141.73 (15)C26—C21—N22—C232.6 (2)
C16—C11—C12—C131.2 (2)N1—C21—N22—C23176.97 (14)
C1—C11—C12—C13179.56 (15)C21—N22—C23—C241.4 (3)
C11—C12—C13—C141.4 (3)N22—C23—C24—C250.7 (3)
C12—C13—C14—F14178.94 (15)C23—C24—C25—C261.6 (3)
C12—C13—C14—C150.7 (3)C24—C25—C26—C210.4 (3)
C13—C14—C15—C160.2 (3)N22—C21—C26—C251.8 (3)
F14—C14—C15—C16179.87 (15)N1—C21—C26—C25177.77 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N22i0.883 (17)2.186 (17)3.0608 (18)171.0 (15)
C16—H16···O1ii0.932.593.266 (2)130
Symmetry codes: (i) x, y, z+1/2; (ii) x, y+1, z1/2.
(Fmo-11-003) 3-Fluoro-N-(pyridin-2-yl)benzamide top
Crystal data top
C12H9FN2OZ = 4
Mr = 216.21F(000) = 448
Triclinic, P1Dx = 1.388 Mg m3
Hall symbol: -P 1Melting point: 350 K
a = 10.4219 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.7183 (4) ÅCell parameters from 8483 reflections
c = 11.0188 (3) Åθ = 2.6–27.5°
α = 102.286 (3)°µ = 0.10 mm1
β = 97.356 (3)°T = 294 K
γ = 117.074 (4)°Block, colourless
V = 1034.49 (8) Å30.44 × 0.35 × 0.28 mm
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
3732 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.016
Graphite monochromatorθmax = 27.9°, θmin = 2.2°
ω scansh = 1313
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
k = 1313
Tmin = 0.956, Tmax = 0.972l = 1414
14851 measured reflections14852 standard reflections every 60 min
4555 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.124 w = 1/[σ2(Fo2) + (0.0528P)2 + 0.2446P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4555 reflectionsΔρmax = 0.29 e Å3
298 parametersΔρmin = 0.25 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.061 (4)
Crystal data top
C12H9FN2Oγ = 117.074 (4)°
Mr = 216.21V = 1034.49 (8) Å3
Triclinic, P1Z = 4
a = 10.4219 (4) ÅMo Kα radiation
b = 10.7183 (4) ŵ = 0.10 mm1
c = 11.0188 (3) ÅT = 294 K
α = 102.286 (3)°0.44 × 0.35 × 0.28 mm
β = 97.356 (3)°
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
3732 reflections with I > 2σ(I)
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
Rint = 0.016
Tmin = 0.956, Tmax = 0.97214852 standard reflections every 60 min
14851 measured reflections intensity decay: 1%
4555 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.29 e Å3
4555 reflectionsΔρmin = 0.25 e Å3
298 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
F13A0.29240 (12)0.41665 (15)0.06770 (12)0.0957 (4)
O1A0.18818 (16)0.88056 (13)0.35345 (12)0.0756 (4)
C1A0.18452 (17)0.76828 (16)0.36305 (14)0.0508 (3)
N1A0.26196 (14)0.76022 (14)0.46787 (11)0.0476 (3)
H1A0.2350 (19)0.671 (2)0.4701 (16)0.059 (5)*
C11A0.08780 (17)0.62419 (16)0.25985 (13)0.0486 (3)
C12A0.05841 (17)0.58739 (18)0.20854 (14)0.0560 (4)
H12A0.09330.65150.23620.067*
C13A0.14950 (18)0.4543 (2)0.11631 (16)0.0628 (4)
C14A0.1022 (2)0.3583 (2)0.06974 (16)0.0659 (4)
H14A0.16680.26900.00650.079*
C15A0.0431 (2)0.39720 (19)0.11872 (16)0.0632 (4)
H15A0.07790.33420.08710.076*
C16A0.13876 (18)0.52877 (17)0.21450 (15)0.0548 (4)
H16A0.23650.55300.24820.066*
C21A0.34021 (15)0.87123 (15)0.58582 (13)0.0451 (3)
N22A0.36302 (15)0.82075 (13)0.68224 (12)0.0543 (3)
C23A0.4290 (2)0.91773 (19)0.80002 (16)0.0649 (4)
H23A0.44430.88340.86820.078*
C24A0.4753 (2)1.06430 (19)0.82632 (17)0.0672 (5)
H24A0.51851.12760.91020.081*
C25A0.45616 (19)1.11517 (18)0.72548 (18)0.0650 (4)
H25A0.48921.21490.74000.078*
C26A0.38830 (17)1.01927 (16)0.60295 (16)0.0556 (4)
H26A0.37491.05240.53350.067*
F13B0.80834 (16)0.83722 (17)1.15646 (12)0.1052 (4)
O1B0.5053 (2)0.43699 (16)0.7306 (2)0.1396 (9)
C1B0.4988 (2)0.54625 (19)0.7277 (2)0.0735 (5)
N1B0.38993 (15)0.54411 (15)0.64410 (13)0.0580 (3)
H1B0.3884 (18)0.6262 (19)0.6562 (15)0.055 (4)*
C11B0.61208 (17)0.69173 (18)0.82037 (17)0.0598 (4)
C12B0.6586 (2)0.6981 (2)0.94706 (19)0.0702 (5)
H12B0.61870.61370.97250.084*
C13B0.7639 (2)0.8309 (2)1.03306 (18)0.0679 (5)
C14B0.8266 (2)0.9564 (2)1.00041 (19)0.0702 (5)
H14B0.89741.04521.06160.084*
C15B0.7834 (2)0.9499 (2)0.87540 (19)0.0720 (5)
H15B0.82681.03470.85100.086*
C16B0.67616 (19)0.8185 (2)0.78540 (18)0.0638 (4)
H16B0.64700.81540.70090.077*
C21B0.26446 (17)0.42092 (16)0.55487 (15)0.0530 (4)
N22B0.16877 (14)0.45414 (13)0.49704 (12)0.0529 (3)
C23B0.04207 (18)0.34301 (17)0.41507 (15)0.0579 (4)
H23B0.02630.36490.37600.069*
C24B0.0070 (2)0.19828 (18)0.38523 (17)0.0649 (4)
H24B0.08250.12410.32750.078*
C25B0.1081 (2)0.16667 (19)0.4432 (2)0.0744 (5)
H25B0.08850.06990.42390.089*
C26B0.2382 (2)0.27780 (19)0.5299 (2)0.0720 (5)
H26B0.30710.25760.57090.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F13A0.0583 (6)0.1072 (9)0.0977 (9)0.0364 (6)0.0014 (6)0.0105 (7)
O1A0.1040 (10)0.0589 (7)0.0684 (7)0.0473 (7)0.0017 (7)0.0244 (6)
C1A0.0593 (8)0.0526 (8)0.0498 (8)0.0328 (7)0.0145 (6)0.0215 (6)
N1A0.0551 (7)0.0409 (6)0.0484 (6)0.0258 (5)0.0081 (5)0.0153 (5)
C11A0.0564 (8)0.0548 (8)0.0413 (7)0.0304 (7)0.0139 (6)0.0205 (6)
C12A0.0598 (9)0.0687 (10)0.0500 (8)0.0389 (8)0.0157 (7)0.0209 (7)
C13A0.0523 (9)0.0734 (11)0.0556 (9)0.0270 (8)0.0088 (7)0.0194 (8)
C14A0.0696 (11)0.0597 (10)0.0542 (9)0.0247 (8)0.0115 (8)0.0112 (7)
C15A0.0759 (11)0.0619 (10)0.0581 (9)0.0394 (9)0.0208 (8)0.0161 (8)
C16A0.0573 (9)0.0603 (9)0.0537 (8)0.0335 (7)0.0146 (7)0.0200 (7)
C21A0.0443 (7)0.0432 (7)0.0516 (7)0.0250 (6)0.0117 (6)0.0149 (6)
N22A0.0641 (8)0.0476 (7)0.0498 (7)0.0301 (6)0.0040 (6)0.0129 (5)
C23A0.0761 (11)0.0638 (10)0.0510 (8)0.0379 (9)0.0029 (8)0.0112 (7)
C24A0.0683 (10)0.0594 (10)0.0601 (9)0.0330 (8)0.0016 (8)0.0016 (8)
C25A0.0610 (9)0.0418 (8)0.0817 (11)0.0239 (7)0.0103 (8)0.0080 (8)
C26A0.0580 (9)0.0450 (8)0.0661 (9)0.0264 (7)0.0151 (7)0.0201 (7)
F13B0.1166 (10)0.1237 (11)0.0768 (8)0.0629 (9)0.0063 (7)0.0372 (7)
O1B0.1113 (13)0.0592 (9)0.214 (2)0.0500 (9)0.0538 (13)0.0162 (11)
C1B0.0654 (10)0.0555 (9)0.1022 (14)0.0379 (8)0.0028 (10)0.0222 (9)
N1B0.0635 (8)0.0452 (7)0.0678 (8)0.0335 (6)0.0056 (6)0.0136 (6)
C11B0.0503 (8)0.0590 (9)0.0777 (11)0.0350 (7)0.0091 (8)0.0217 (8)
C12B0.0640 (10)0.0721 (11)0.0917 (13)0.0414 (9)0.0178 (9)0.0415 (10)
C13B0.0626 (10)0.0834 (12)0.0664 (10)0.0446 (10)0.0107 (8)0.0235 (9)
C14B0.0578 (10)0.0683 (11)0.0796 (12)0.0318 (9)0.0124 (9)0.0158 (9)
C15B0.0609 (10)0.0652 (11)0.0854 (13)0.0252 (9)0.0184 (9)0.0296 (9)
C16B0.0583 (9)0.0695 (11)0.0674 (10)0.0330 (8)0.0152 (8)0.0260 (8)
C21B0.0595 (9)0.0476 (8)0.0585 (8)0.0311 (7)0.0181 (7)0.0169 (7)
N22B0.0581 (7)0.0468 (7)0.0535 (7)0.0258 (6)0.0118 (6)0.0174 (5)
C23B0.0574 (9)0.0549 (9)0.0577 (9)0.0240 (7)0.0163 (7)0.0189 (7)
C24B0.0603 (9)0.0517 (9)0.0684 (10)0.0185 (8)0.0224 (8)0.0101 (8)
C25B0.0814 (12)0.0445 (9)0.0943 (13)0.0315 (9)0.0293 (11)0.0113 (9)
C26B0.0766 (11)0.0517 (9)0.0914 (13)0.0399 (9)0.0149 (10)0.0145 (9)
Geometric parameters (Å, º) top
F13A—C13A1.3508 (19)F13B—C13B1.356 (2)
O1A—C1A1.2142 (17)O1B—C1B1.210 (2)
C1A—N1A1.3638 (18)C1B—N1B1.355 (2)
C1A—C11A1.495 (2)C1B—C11B1.485 (2)
N1A—C21A1.3990 (18)N1B—C21B1.402 (2)
N1A—H1A0.876 (18)N1B—H1B0.870 (17)
C11A—C16A1.387 (2)C11B—C16B1.380 (2)
C11A—C12A1.391 (2)C11B—C12B1.394 (2)
C12A—C13A1.369 (2)C12B—C13B1.366 (3)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.366 (3)C13B—C14B1.354 (3)
C14A—C15A1.370 (2)C14B—C15B1.370 (3)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.383 (2)C15B—C16B1.380 (3)
C15A—H15A0.9300C15B—H15B0.9300
C16A—H16A0.9300C16B—H16B0.9300
C21A—N22A1.3324 (18)C21B—N22B1.3358 (19)
C21A—C26A1.3889 (19)C21B—C26B1.387 (2)
N22A—C23A1.336 (2)N22B—C23B1.335 (2)
C23A—C24A1.366 (2)C23B—C24B1.373 (2)
C23A—H23A0.9300C23B—H23B0.9300
C24A—C25A1.368 (3)C24B—C25B1.370 (3)
C24A—H24A0.9300C24B—H24B0.9300
C25A—C26A1.372 (2)C25B—C26B1.373 (3)
C25A—H25A0.9300C25B—H25B0.9300
C26A—H26A0.9300C26B—H26B0.9300
O1A—C1A—N1A124.10 (14)O1B—C1B—N1B123.31 (18)
O1A—C1A—C11A121.53 (13)O1B—C1B—C11B120.10 (16)
N1A—C1A—C11A114.34 (12)N1B—C1B—C11B116.57 (14)
C1A—N1A—C21A126.24 (12)C1B—N1B—C21B127.75 (14)
C1A—N1A—H1A114.9 (11)C1B—N1B—H1B116.2 (11)
C21A—N1A—H1A115.5 (11)C21B—N1B—H1B115.0 (11)
C16A—C11A—C12A119.90 (14)C16B—C11B—C12B119.09 (17)
C16A—C11A—C1A122.62 (13)C16B—C11B—C1B122.90 (17)
C12A—C11A—C1A117.48 (13)C12B—C11B—C1B117.97 (16)
C13A—C12A—C11A118.22 (15)C13B—C12B—C11B118.63 (17)
C13A—C12A—H12A120.9C13B—C12B—H12B120.7
C11A—C12A—H12A120.9C11B—C12B—H12B120.7
F13A—C13A—C14A118.37 (16)C14B—C13B—F13B118.47 (18)
F13A—C13A—C12A118.54 (16)C14B—C13B—C12B122.90 (17)
C14A—C13A—C12A123.09 (15)F13B—C13B—C12B118.62 (17)
C13A—C14A—C15A118.20 (16)C13B—C14B—C15B118.58 (18)
C13A—C14A—H14A120.9C13B—C14B—H14B120.7
C15A—C14A—H14A120.9C15B—C14B—H14B120.7
C14A—C15A—C16A121.05 (16)C14B—C15B—C16B120.58 (18)
C14A—C15A—H15A119.5C14B—C15B—H15B119.7
C16A—C15A—H15A119.5C16B—C15B—H15B119.7
C15A—C16A—C11A119.51 (15)C11B—C16B—C15B120.19 (17)
C15A—C16A—H16A120.2C11B—C16B—H16B119.9
C11A—C16A—H16A120.2C15B—C16B—H16B119.9
N22A—C21A—C26A122.64 (13)N22B—C21B—C26B122.49 (15)
N22A—C21A—N1A113.16 (12)N22B—C21B—N1B113.14 (12)
C26A—C21A—N1A124.19 (13)C26B—C21B—N1B124.35 (15)
C21A—N22A—C23A117.37 (13)C23B—N22B—C21B117.57 (13)
N22A—C23A—C24A123.90 (16)N22B—C23B—C24B123.71 (16)
N22A—C23A—H23A118.1N22B—C23B—H23B118.1
C24A—C23A—H23A118.1C24B—C23B—H23B118.1
C23A—C24A—C25A117.92 (15)C25B—C24B—C23B117.88 (16)
C23A—C24A—H24A121.0C25B—C24B—H24B121.1
C25A—C24A—H24A121.0C23B—C24B—H24B121.1
C24A—C25A—C26A120.10 (15)C24B—C25B—C26B120.01 (16)
C24A—C25A—H25A119.9C24B—C25B—H25B120.0
C26A—C25A—H25A119.9C26B—C25B—H25B120.0
C25A—C26A—C21A117.98 (15)C25B—C26B—C21B118.31 (17)
C25A—C26A—H26A121.0C25B—C26B—H26B120.8
C21A—C26A—H26A121.0C21B—C26B—H26B120.8
O1A—C1A—N1A—C21A9.2 (3)O1B—C1B—N1B—C21B4.4 (4)
C11A—C1A—N1A—C21A168.63 (13)C11B—C1B—N1B—C21B174.48 (16)
O1A—C1A—C11A—C16A134.13 (17)O1B—C1B—C11B—C16B137.5 (2)
N1A—C1A—C11A—C16A47.96 (19)N1B—C1B—C11B—C16B43.6 (3)
O1A—C1A—C11A—C12A45.6 (2)O1B—C1B—C11B—C12B40.2 (3)
N1A—C1A—C11A—C12A132.35 (14)N1B—C1B—C11B—C12B138.65 (18)
C16A—C11A—C12A—C13A1.9 (2)C16B—C11B—C12B—C13B1.5 (2)
C1A—C11A—C12A—C13A178.38 (13)C1B—C11B—C12B—C13B179.32 (16)
C11A—C12A—C13A—F13A178.83 (14)C11B—C12B—C13B—C14B0.9 (3)
C11A—C12A—C13A—C14A2.1 (2)C11B—C12B—C13B—F13B179.57 (16)
F13A—C13A—C14A—C15A179.61 (16)F13B—C13B—C14B—C15B179.05 (17)
C12A—C13A—C14A—C15A0.5 (3)C12B—C13B—C14B—C15B0.5 (3)
C13A—C14A—C15A—C16A1.2 (3)C13B—C14B—C15B—C16B1.2 (3)
C14A—C15A—C16A—C11A1.3 (2)C12B—C11B—C16B—C15B0.8 (3)
C12A—C11A—C16A—C15A0.3 (2)C1B—C11B—C16B—C15B178.52 (16)
C1A—C11A—C16A—C15A179.96 (14)C14B—C15B—C16B—C11B0.6 (3)
C1A—N1A—C21A—N22A159.10 (14)C1B—N1B—C21B—N22B172.50 (17)
C1A—N1A—C21A—C26A20.0 (2)C1B—N1B—C21B—C26B6.0 (3)
C26A—C21A—N22A—C23A3.1 (2)C26B—C21B—N22B—C23B1.8 (2)
N1A—C21A—N22A—C23A176.05 (14)N1B—C21B—N22B—C23B176.72 (13)
C21A—N22A—C23A—C24A0.8 (3)C21B—N22B—C23B—C24B1.5 (2)
N22A—C23A—C24A—C25A1.7 (3)N22B—C23B—C24B—C25B0.1 (3)
C23A—C24A—C25A—C26A1.9 (3)C23B—C24B—C25B—C26B1.2 (3)
C24A—C25A—C26A—C21A0.2 (2)C24B—C25B—C26B—C21B0.9 (3)
N22A—C21A—C26A—C25A2.9 (2)N22B—C21B—C26B—C25B0.6 (3)
N1A—C21A—C26A—C25A176.20 (14)N1B—C21B—C26B—C25B177.76 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···N22B0.876 (18)2.199 (18)3.0721 (17)174.1 (15)
N1B—H1B···N22A0.870 (17)2.183 (18)3.0502 (18)174.9 (15)
C26A—H26A···O1A0.932.302.844 (2)117
C26B—H26B···O1B0.932.252.836 (3)120
C25A—H25A···O1Bi0.932.333.235 (2)163
Symmetry code: (i) x, y+1, z.
(Foo-10-128) 2-Fluoro-N-(pyridin-2-yl)benzamide top
Crystal data top
C12H9FN2OZ = 4
Mr = 216.21F(000) = 448
Triclinic, P1Dx = 1.369 Mg m3
Hall symbol: -P 1Melting point: 358 K
a = 9.7560 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.7699 (5) ÅCell parameters from 5781 reflections
c = 11.9694 (2) Åθ = 2.6–27.5°
α = 64.412 (4)°µ = 0.10 mm1
β = 68.453 (4)°T = 294 K
γ = 86.091 (4)°Block, colourless
V = 1048.88 (7) Å30.42 × 0.35 × 0.28 mm
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
4377 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.012
Graphite monochromatorθmax = 29.5°, θmin = 2.2°
ω scansh = 1311
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
k = 1214
Tmin = 0.959, Tmax = 0.972l = 1616
9959 measured reflections9959 standard reflections every 60 min
5437 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0447P)2 + 0.216P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
5437 reflectionsΔρmax = 0.31 e Å3
298 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.035 (3)
Crystal data top
C12H9FN2Oγ = 86.091 (4)°
Mr = 216.21V = 1048.88 (7) Å3
Triclinic, P1Z = 4
a = 9.7560 (4) ÅMo Kα radiation
b = 10.7699 (5) ŵ = 0.10 mm1
c = 11.9694 (2) ÅT = 294 K
α = 64.412 (4)°0.42 × 0.35 × 0.28 mm
β = 68.453 (4)°
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
4377 reflections with I > 2σ(I)
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
Rint = 0.012
Tmin = 0.959, Tmax = 0.9729959 standard reflections every 60 min
9959 measured reflections intensity decay: 1%
5437 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.31 e Å3
5437 reflectionsΔρmin = 0.23 e Å3
298 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
F12A0.44608 (10)0.15810 (11)0.99747 (10)0.0817 (3)
O1A0.14647 (19)0.36665 (12)1.05131 (13)0.0859 (4)
C1A0.17178 (16)0.26512 (13)1.03041 (13)0.0466 (3)
N1A0.17746 (13)0.25815 (11)0.91872 (11)0.0433 (2)
H1A0.1905 (17)0.1788 (17)0.9155 (15)0.052 (4)*
C11A0.19731 (14)0.13474 (12)1.13396 (12)0.0407 (3)
C12A0.33450 (15)0.08708 (14)1.11610 (14)0.0493 (3)
C13A0.36249 (18)0.02679 (16)1.21334 (17)0.0597 (4)
H13A0.45700.05541.19810.072*
C14A0.24829 (19)0.09719 (15)1.33315 (16)0.0604 (4)
H14A0.26510.17461.40010.073*
C15A0.10918 (19)0.05416 (16)1.35487 (15)0.0590 (4)
H15A0.03170.10351.43590.071*
C16A0.08369 (16)0.06220 (14)1.25678 (14)0.0500 (3)
H16A0.01030.09211.27320.060*
C21A0.15369 (13)0.36230 (12)0.80825 (12)0.0398 (3)
N22A0.17228 (12)0.32449 (11)0.71143 (10)0.0449 (2)
C23A0.14592 (16)0.41515 (15)0.60424 (14)0.0524 (3)
H23A0.15720.38940.53680.063*
C24A0.10321 (18)0.54368 (15)0.58823 (15)0.0581 (4)
H24A0.08560.60350.51230.070*
C25A0.08719 (19)0.58147 (14)0.68810 (16)0.0607 (4)
H25A0.05940.66850.67970.073*
C26A0.11215 (17)0.49101 (13)0.80038 (14)0.0517 (3)
H26A0.10160.51510.86870.062*
F12B0.50683 (11)0.29122 (10)0.54275 (10)0.0708 (3)
O1B0.32217 (15)0.03366 (11)0.55100 (11)0.0693 (3)
C1B0.32722 (15)0.06731 (14)0.57071 (13)0.0458 (3)
N1B0.29127 (13)0.06240 (11)0.69386 (11)0.0462 (3)
H1B0.2719 (17)0.1386 (17)0.7022 (15)0.054 (4)*
C11B0.36783 (14)0.21001 (13)0.45761 (13)0.0446 (3)
C12B0.45352 (15)0.31498 (15)0.44635 (14)0.0506 (3)
C13B0.48772 (18)0.44457 (17)0.34028 (17)0.0653 (4)
H13B0.54570.51300.33570.078*
C14B0.4347 (2)0.47132 (18)0.24110 (18)0.0731 (5)
H14B0.45640.55870.16920.088*
C15B0.3500 (2)0.36969 (18)0.24784 (17)0.0697 (4)
H15B0.31430.38820.18070.084*
C16B0.31819 (18)0.24044 (16)0.35404 (14)0.0559 (3)
H16B0.26230.17180.35690.067*
C21B0.25986 (14)0.05504 (12)0.81614 (13)0.0412 (3)
N22B0.20880 (13)0.02642 (11)0.92156 (11)0.0463 (3)
C23B0.17916 (17)0.13237 (14)1.04274 (14)0.0513 (3)
H23B0.14170.11391.11690.062*
C24B0.20098 (17)0.26650 (14)1.06348 (15)0.0540 (3)
H24B0.18090.33691.14910.065*
C25B0.25350 (19)0.29377 (14)0.95390 (16)0.0604 (4)
H25B0.26890.38380.96500.072*
C26B0.28339 (18)0.18834 (14)0.82792 (15)0.0552 (3)
H26B0.31820.20550.75300.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F12A0.0523 (5)0.0801 (7)0.0734 (6)0.0050 (5)0.0019 (5)0.0170 (5)
O1A0.1636 (14)0.0540 (6)0.0800 (8)0.0451 (8)0.0752 (9)0.0445 (6)
C1A0.0591 (8)0.0405 (6)0.0484 (7)0.0112 (6)0.0254 (6)0.0233 (6)
N1A0.0579 (7)0.0340 (5)0.0437 (6)0.0120 (5)0.0229 (5)0.0198 (4)
C11A0.0479 (7)0.0390 (6)0.0425 (6)0.0070 (5)0.0209 (5)0.0214 (5)
C12A0.0451 (7)0.0486 (7)0.0500 (7)0.0037 (5)0.0151 (6)0.0200 (6)
C13A0.0547 (8)0.0564 (8)0.0763 (10)0.0170 (7)0.0368 (8)0.0279 (8)
C14A0.0794 (11)0.0473 (8)0.0591 (9)0.0080 (7)0.0407 (8)0.0153 (7)
C15A0.0682 (10)0.0531 (8)0.0440 (7)0.0044 (7)0.0155 (7)0.0143 (6)
C16A0.0468 (7)0.0533 (8)0.0512 (7)0.0062 (6)0.0163 (6)0.0257 (6)
C21A0.0413 (6)0.0353 (6)0.0417 (6)0.0060 (5)0.0156 (5)0.0161 (5)
N22A0.0512 (6)0.0433 (6)0.0434 (6)0.0124 (5)0.0200 (5)0.0209 (5)
C23A0.0609 (8)0.0545 (8)0.0457 (7)0.0154 (6)0.0245 (6)0.0229 (6)
C24A0.0708 (10)0.0479 (7)0.0522 (8)0.0143 (7)0.0307 (7)0.0139 (6)
C25A0.0812 (11)0.0380 (7)0.0658 (9)0.0183 (7)0.0355 (8)0.0206 (7)
C26A0.0691 (9)0.0384 (6)0.0531 (8)0.0132 (6)0.0272 (7)0.0223 (6)
F12B0.0692 (6)0.0755 (6)0.0790 (6)0.0043 (5)0.0406 (5)0.0315 (5)
O1B0.1119 (10)0.0497 (6)0.0601 (6)0.0080 (6)0.0360 (6)0.0329 (5)
C1B0.0519 (7)0.0451 (7)0.0482 (7)0.0079 (5)0.0209 (6)0.0258 (6)
N1B0.0619 (7)0.0362 (5)0.0448 (6)0.0094 (5)0.0201 (5)0.0220 (5)
C11B0.0455 (7)0.0471 (7)0.0434 (7)0.0074 (5)0.0146 (5)0.0238 (6)
C12B0.0432 (7)0.0565 (8)0.0538 (8)0.0037 (6)0.0171 (6)0.0264 (6)
C13B0.0543 (9)0.0564 (9)0.0708 (10)0.0091 (7)0.0141 (8)0.0210 (8)
C14B0.0781 (11)0.0573 (9)0.0592 (10)0.0015 (8)0.0197 (9)0.0078 (8)
C15B0.0865 (12)0.0677 (10)0.0530 (9)0.0081 (9)0.0336 (9)0.0187 (8)
C16B0.0670 (9)0.0567 (8)0.0504 (8)0.0048 (7)0.0254 (7)0.0259 (7)
C21B0.0433 (6)0.0367 (6)0.0467 (7)0.0049 (5)0.0186 (5)0.0196 (5)
N22B0.0577 (7)0.0374 (5)0.0451 (6)0.0043 (5)0.0191 (5)0.0193 (5)
C23B0.0615 (8)0.0437 (7)0.0453 (7)0.0008 (6)0.0175 (6)0.0177 (6)
C24B0.0586 (8)0.0403 (7)0.0533 (8)0.0001 (6)0.0217 (7)0.0108 (6)
C25B0.0729 (10)0.0356 (7)0.0699 (10)0.0106 (6)0.0272 (8)0.0210 (7)
C26B0.0698 (9)0.0423 (7)0.0582 (8)0.0129 (6)0.0230 (7)0.0280 (6)
Geometric parameters (Å, º) top
F12A—C12A1.3515 (16)F12B—C12B1.3547 (16)
O1A—C1A1.2138 (15)O1B—C1B1.2158 (15)
C1A—N1A1.3519 (16)C1B—N1B1.3616 (16)
C1A—C11A1.4986 (17)C1B—C11B1.4979 (19)
N1A—C21A1.4032 (15)N1B—C21B1.4000 (16)
N1A—H1A0.871 (16)N1B—H1B0.870 (16)
C11A—C12A1.3754 (18)C11B—C12B1.3818 (19)
C11A—C16A1.3890 (18)C11B—C16B1.3954 (19)
C12A—C13A1.374 (2)C12B—C13B1.376 (2)
C13A—C14A1.369 (2)C13B—C14B1.377 (2)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.372 (2)C14B—C15B1.373 (3)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.383 (2)C15B—C16B1.375 (2)
C15A—H15A0.9300C15B—H15B0.9300
C16A—H16A0.9300C16B—H16B0.9300
C21A—N22A1.3360 (15)C21B—N22B1.3373 (16)
C21A—C26A1.3904 (17)C21B—C26B1.3920 (17)
N22A—C23A1.3385 (16)N22B—C23B1.3404 (17)
C23A—C24A1.370 (2)C23B—C24B1.3715 (19)
C23A—H23A0.9300C23B—H23B0.9300
C24A—C25A1.376 (2)C24B—C25B1.374 (2)
C24A—H24A0.9300C24B—H24B0.9300
C25A—C26A1.375 (2)C25B—C26B1.375 (2)
C25A—H25A0.9300C25B—H25B0.9300
C26A—H26A0.9300C26B—H26B0.9300
O1A—C1A—N1A124.86 (12)O1B—C1B—N1B124.18 (13)
O1A—C1A—C11A119.68 (12)O1B—C1B—C11B120.95 (12)
N1A—C1A—C11A115.45 (10)N1B—C1B—C11B114.81 (11)
C1A—N1A—C21A127.63 (10)C1B—N1B—C21B127.86 (11)
C1A—N1A—H1A117.9 (10)C1B—N1B—H1B118.1 (10)
C21A—N1A—H1A114.3 (10)C21B—N1B—H1B113.4 (10)
C12A—C11A—C16A117.21 (12)C12B—C11B—C16B116.72 (13)
C12A—C11A—C1A122.16 (12)C12B—C11B—C1B124.88 (12)
C16A—C11A—C1A120.49 (12)C16B—C11B—C1B118.40 (12)
F12A—C12A—C13A119.37 (13)F12B—C12B—C13B117.83 (13)
F12A—C12A—C11A117.57 (12)F12B—C12B—C11B119.51 (13)
C13A—C12A—C11A123.05 (13)C13B—C12B—C11B122.65 (14)
C14A—C13A—C12A118.59 (14)C12B—C13B—C14B118.93 (15)
C14A—C13A—H13A120.7C12B—C13B—H13B120.5
C12A—C13A—H13A120.7C14B—C13B—H13B120.5
C13A—C14A—C15A120.34 (14)C15B—C14B—C13B120.34 (16)
C13A—C14A—H14A119.8C15B—C14B—H14B119.8
C15A—C14A—H14A119.8C13B—C14B—H14B119.8
C14A—C15A—C16A120.26 (14)C14B—C15B—C16B119.86 (16)
C14A—C15A—H15A119.9C14B—C15B—H15B120.1
C16A—C15A—H15A119.9C16B—C15B—H15B120.1
C15A—C16A—C11A120.52 (13)C15B—C16B—C11B121.49 (15)
C15A—C16A—H16A119.7C15B—C16B—H16B119.3
C11A—C16A—H16A119.7C11B—C16B—H16B119.3
N22A—C21A—C26A122.99 (11)N22B—C21B—C26B122.80 (12)
N22A—C21A—N1A113.10 (10)N22B—C21B—N1B113.34 (10)
C26A—C21A—N1A123.90 (11)C26B—C21B—N1B123.83 (12)
C21A—N22A—C23A117.39 (11)C21B—N22B—C23B117.48 (11)
N22A—C23A—C24A123.76 (13)N22B—C23B—C24B123.65 (13)
N22A—C23A—H23A118.1N22B—C23B—H23B118.2
C24A—C23A—H23A118.1C24B—C23B—H23B118.2
C23A—C24A—C25A117.90 (13)C23B—C24B—C25B117.98 (13)
C23A—C24A—H24A121.1C23B—C24B—H24B121.0
C25A—C24A—H24A121.1C25B—C24B—H24B121.0
C26A—C25A—C24A120.20 (13)C24B—C25B—C26B120.23 (13)
C26A—C25A—H25A119.9C24B—C25B—H25B119.9
C24A—C25A—H25A119.9C26B—C25B—H25B119.9
C25A—C26A—C21A117.74 (13)C25B—C26B—C21B117.86 (13)
C25A—C26A—H26A121.1C25B—C26B—H26B121.1
C21A—C26A—H26A121.1C21B—C26B—H26B121.1
O1A—C1A—N1A—C21A1.1 (2)O1B—C1B—N1B—C21B8.1 (2)
C11A—C1A—N1A—C21A178.01 (12)C11B—C1B—N1B—C21B174.76 (12)
O1A—C1A—C11A—C12A109.55 (17)O1B—C1B—C11B—C12B142.07 (15)
N1A—C1A—C11A—C12A71.26 (17)N1B—C1B—C11B—C12B40.69 (18)
O1A—C1A—C11A—C16A65.87 (19)O1B—C1B—C11B—C16B36.9 (2)
N1A—C1A—C11A—C16A113.32 (14)N1B—C1B—C11B—C16B140.30 (13)
C16A—C11A—C12A—F12A179.19 (12)C16B—C11B—C12B—F12B179.06 (12)
C1A—C11A—C12A—F12A3.63 (19)C1B—C11B—C12B—F12B0.0 (2)
C16A—C11A—C12A—C13A0.2 (2)C16B—C11B—C12B—C13B1.0 (2)
C1A—C11A—C12A—C13A175.36 (13)C1B—C11B—C12B—C13B179.98 (13)
F12A—C12A—C13A—C14A179.73 (14)F12B—C12B—C13B—C14B179.94 (15)
C11A—C12A—C13A—C14A0.8 (2)C11B—C12B—C13B—C14B0.0 (2)
C12A—C13A—C14A—C15A0.1 (2)C12B—C13B—C14B—C15B0.5 (3)
C13A—C14A—C15A—C16A1.2 (2)C13B—C14B—C15B—C16B0.1 (3)
C14A—C15A—C16A—C11A1.7 (2)C14B—C15B—C16B—C11B1.2 (3)
C12A—C11A—C16A—C15A1.05 (19)C12B—C11B—C16B—C15B1.6 (2)
C1A—C11A—C16A—C15A176.69 (12)C1B—C11B—C16B—C15B179.31 (14)
C1A—N1A—C21A—N22A177.88 (13)C1B—N1B—C21B—N22B171.38 (13)
C1A—N1A—C21A—C26A3.3 (2)C1B—N1B—C21B—C26B10.6 (2)
C26A—C21A—N22A—C23A1.5 (2)C26B—C21B—N22B—C23B0.3 (2)
N1A—C21A—N22A—C23A177.29 (12)N1B—C21B—N22B—C23B178.40 (12)
C21A—N22A—C23A—C24A0.8 (2)C21B—N22B—C23B—C24B1.3 (2)
N22A—C23A—C24A—C25A0.3 (2)N22B—C23B—C24B—C25B1.3 (2)
C23A—C24A—C25A—C26A0.7 (3)C23B—C24B—C25B—C26B0.3 (2)
C24A—C25A—C26A—C21A0.1 (2)C24B—C25B—C26B—C21B0.5 (2)
N22A—C21A—C26A—C25A1.1 (2)N22B—C21B—C26B—C25B0.5 (2)
N1A—C21A—C26A—C25A177.61 (14)N1B—C21B—C26B—C25B177.33 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···N22B0.871 (16)2.177 (16)3.0460 (14)175.7 (14)
N1B—H1B···N22A0.870 (16)2.193 (16)3.0408 (15)164.8 (14)
N1B—H1B···F12B0.870 (16)2.487 (16)2.7981 (15)101.8 (12)
C26A—H26A···O1A0.932.262.8513 (18)121
C26B—H26B···O1B0.932.312.8810 (19)119

Experimental details

(Fpp-10-124)(Fmp-10-126)(Fop-10-125)(Fpm_O-10-127)
Crystal data
Chemical formulaC12H9FN2OC12H9FN2OC12H9FN2OC12H9FN2O
Mr216.21216.21216.21216.21
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/n
Temperature (K)294294294294
a, b, c (Å)5.6777 (1), 11.4769 (2), 15.5289 (3)5.7961 (1), 11.3050 (2), 15.2384 (2)6.0388 (1), 11.2502 (2), 14.9265 (3)13.9411 (3), 5.2040 (1), 15.0752 (3)
α, β, γ (°)90, 95.974 (2), 9090, 94.238 (1), 9090, 95.310 (2), 9090, 114.812 (3), 90
V3)1006.40 (3)995.76 (3)1009.72 (3)992.74 (3)
Z4444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.110.110.110.11
Crystal size (mm)0.39 × 0.25 × 0.190.37 × 0.34 × 0.190.45 × 0.30 × 0.080.51 × 0.49 × 0.32
Data collection
DiffractometerXcalibur, Sapphire3, Gemini Ultra
diffractometer
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
Absorption correctionAnalytical
(ABSFAC, Clark and Reid, 1998)
Analytical
(ABSFAC, Clark and Reid, 1998)
Analytical
(ABSFAC, Clark and Reid, 1998)
Analytical
(ABSFAC, Clark and Reid, 1998)
Tmin, Tmax0.960, 0.9800.961, 0.9800.954, 0.9920.947, 0.966
No. of measured, independent and
observed [I > 2σ(I)] reflections
7351, 2216, 1979 7728, 2202, 1988 7133, 2256, 1914 8861, 2624, 2338
Rint0.0130.0120.0160.012
θmax (°)27.827.827.929.6
(sin θ/λ)max1)0.6560.6560.6580.695
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.090, 1.04 0.034, 0.092, 1.05 0.037, 0.103, 1.02 0.042, 0.114, 1.03
No. of reflections2216220222562624
No. of parameters150150150150
No. of restraints0000
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.140.24, 0.170.23, 0.160.25, 0.19
Absolute structure????
Absolute structure parameter????


(Fpm_N-10-121)(Fmm-10-122)(Fom_O-11-009)(Fom_F-11-061)
Crystal data
Chemical formulaC12H9FN2OC12H9FN2OC12H9FN2OC12H9FN2O
Mr216.21216.21216.21216.21
Crystal system, space groupMonoclinic, P21/nOrthorhombic, Pca21Monoclinic, P21Monoclinic, P21/n
Temperature (K)294294294294
a, b, c (Å)3.9077 (2), 24.2444 (12), 10.7012 (5)11.3020 (3), 11.8371 (3), 7.6218 (2)16.2051 (4), 5.2239 (1), 35.8162 (9)5.4788 (2), 8.8223 (4), 20.4414 (7)
α, β, γ (°)90, 95.181 (5), 9090, 90, 9090, 98.405 (3), 9090, 92.150 (4), 90
V3)1009.69 (9)1019.67 (5)2999.41 (12)987.35 (7)
Z44124
Radiation typeMo KαMo KαCu KαMo Kα
µ (mm1)0.110.110.890.11
Crystal size (mm)0.24 × 0.05 × 0.030.38 × 0.10 × 0.080.47 × 0.23 × 0.160.49 × 0.25 × 0.12
Data collection
DiffractometerXcalibur, Sapphire3, Gemini Ultra
diffractometer
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
Absorption correctionAnalytical
(ABSFAC, Clark and Reid, 1998)
Analytical
(ABSFAC, Clark and Reid, 1998)
Analytical
(ABSFAC, Clark and Reid, 1998)
Analytical
(ABSFAC, Clark and Reid, 1998)
Tmin, Tmax0.975, 0.9970.961, 0.9920.679, 0.8700.949, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
6537, 2162, 1154 7366, 1239, 981 13035, 5835, 5064 7439, 2178, 1599
Rint0.0490.0210.0260.027
θmax (°)27.427.858.327.8
(sin θ/λ)max1)0.6470.6560.5520.655
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.120, 0.96 0.033, 0.084, 1.02 0.059, 0.176, 1.06 0.044, 0.122, 1.05
No. of reflections2162123958352178
No. of parameters1491491315149
No. of restraints016380
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrainedH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.16, 0.160.15, 0.150.16, 0.190.14, 0.18
Absolute structure??(Flack, 1983)?
Absolute structure parameter??0.0 (13)?


(Fpo-10-123)(Fmo-11-003)(Foo-10-128)
Crystal data
Chemical formulaC12H9FN2OC12H9FN2OC12H9FN2O
Mr216.21216.21216.21
Crystal system, space groupOrthorhombic, PbcnTriclinic, P1Triclinic, P1
Temperature (K)294294294
a, b, c (Å)24.3381 (4), 7.9334 (1), 10.8791 (2)10.4219 (4), 10.7183 (4), 11.0188 (3)9.7560 (4), 10.7699 (5), 11.9694 (2)
α, β, γ (°)90, 90, 90102.286 (3), 97.356 (3), 117.074 (4)64.412 (4), 68.453 (4), 86.091 (4)
V3)2100.58 (6)1034.49 (8)1048.88 (7)
Z844
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.100.100.10
Crystal size (mm)0.58 × 0.53 × 0.170.44 × 0.35 × 0.280.42 × 0.35 × 0.28
Data collection
DiffractometerXcalibur, Sapphire3, Gemini Ultra
diffractometer
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
Absorption correctionAnalytical
(ABSFAC, Clark and Reid, 1998)
Analytical
(ABSFAC, Clark and Reid, 1998)
Analytical
(ABSFAC, Clark and Reid, 1998)
Tmin, Tmax0.943, 0.9830.956, 0.9720.959, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
14121, 2254, 1829 14851, 4555, 3732 9959, 5437, 4377
Rint0.0240.0160.012
θmax (°)27.127.929.5
(sin θ/λ)max1)0.6400.6590.692
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.113, 1.04 0.046, 0.124, 1.03 0.044, 0.114, 1.04
No. of reflections225445555437
No. of parameters150298298
No. of restraints000
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.14, 0.170.29, 0.250.31, 0.23
Absolute structure???
Absolute structure parameter???

Computer programs: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995), PLATON (Spek, 2009), SHELXL97.

Hydrogen-bond geometry (Å, º) for (Fpp-10-124) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N24i0.848 (16)2.335 (17)3.0581 (15)143.5 (14)
C26—H26···O10.932.332.8738 (15)117
C26—H26···Cg1ii0.932.773.4183 (12)127
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+2, y, z+1.
Hydrogen-bond geometry (Å, º) for (Fmp-10-126) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N24i0.852 (15)2.333 (16)3.0786 (14)146.5 (13)
C26—H26···O10.932.322.8819 (14)118
Symmetry code: (i) x+1, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (Fop-10-125) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N24i0.862 (18)2.356 (18)3.0587 (16)138.9 (15)
N1—H1···F120.862 (18)2.332 (17)2.7491 (13)110.0 (13)
Symmetry code: (i) x+1, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (Fpm_O-10-127) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.859 (17)2.221 (17)3.0575 (13)164.6 (14)
C26—H26···O10.932.452.8987 (15)109
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) for (Fpm_N-10-121) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N23i0.84 (3)2.32 (3)3.151 (3)167 (2)
C22—H22···O10.932.212.828 (3)123
C16—H16···N23i0.932.603.404 (3)146
C26—H26···N23i0.932.603.390 (3)144
Symmetry code: (i) x1/2, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) for (Fmm-10-122) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N23i0.77 (3)2.31 (3)3.077 (3)176 (3)
C22—H22···O10.932.222.829 (3)123
Symmetry code: (i) x+1/2, y+1, z.
Hydrogen-bond geometry (Å, º) for (Fom_O-11-009) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1Ai0.862.323.117 (8)154
N1B—H1B···O1Bii0.862.313.099 (10)153
N1C—H1C···O1Ci0.862.293.074 (8)152
N1D—H1D···O1Dii0.862.293.093 (9)157
N1E—H1E···O1Ei0.862.353.15 (3)155
N1G—H1G···O1Gi0.862.253.05 (3)155
N1F—H1F···O1Fii0.862.363.15 (2)153
N1H—H1H···O1Hii0.862.293.08 (3)153
N1A—H1A···F12A0.862.262.766 (5)118
N1B—H1B···F12B0.862.192.720 (5)119
N1C—H1C···F12C0.862.202.727 (5)119
N1D—H1D···F12D0.862.222.723 (5)117
N1E—H1E···F12E0.862.262.773 (9)118
N1F—H1F···F12F0.862.162.698 (9)120
N1G—H1G···F12G0.862.182.727 (11)122
N1H—H1H···F12H0.862.192.720 (10)120
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.
Hydrogen-bond geometry (Å, º) for (Fom_F-11-061) top
D—H···AD—HH···AD···AD—H···A
N1—H1···F120.850 (17)2.074 (17)2.7315 (16)133.7 (15)
C16—H16···O10.932.462.7777 (19)100
C22—H22···O10.932.302.867 (2)119
Hydrogen-bond geometry (Å, º) for (Fpo-10-123) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N22i0.883 (17)2.186 (17)3.0608 (18)171.0 (15)
C16—H16···O1ii0.932.593.266 (2)130
Symmetry codes: (i) x, y, z+1/2; (ii) x, y+1, z1/2.
Hydrogen-bond geometry (Å, º) for (Fmo-11-003) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···N22B0.876 (18)2.199 (18)3.0721 (17)174.1 (15)
N1B—H1B···N22A0.870 (17)2.183 (18)3.0502 (18)174.9 (15)
C26A—H26A···O1A0.932.302.844 (2)117
C26B—H26B···O1B0.932.252.836 (3)120
C25A—H25A···O1Bi0.932.333.235 (2)163
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) for (Foo-10-128) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···N22B0.871 (16)2.177 (16)3.0460 (14)175.7 (14)
N1B—H1B···N22A0.870 (16)2.193 (16)3.0408 (15)164.8 (14)
N1B—H1B···F12B0.870 (16)2.487 (16)2.7981 (15)101.8 (12)
C26A—H26A···O1A0.932.262.8513 (18)121
C26B—H26B···O1B0.932.312.8810 (19)119
 

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds