Crystal structures of three N-(pyridine-2-carbon­yl)pyridine-2-carboxamides as potential ligands for supra­molecular chemistry

The crystal structures of three N-(pyridine-2-carbon­yl)pyridine-2-carboxamide ligands, with or without F atoms on the 3-position of the pyridine ring, with potential use in supra­molecular chemistry are reported.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• Mean [sigma](C-C) = 0.007 Å
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.060
• wR factor = 0.170
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0055 Ang.

Alert level G
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.300 Report
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.12 Report
PLAT850_ALERT_4_G Check Flack Parameter Exact Value 0.00 with s.u.       0.30 Check
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          5 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 2


Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       7.02 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0067 Ang.

Alert level G
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.300 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         6% Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...         11 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 3


Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5       ..O1       .       2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3       ..F1       .       2.58 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5       ..F1       .       2.66 Ang.

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   0 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

N-(Pyridine-2-carbonyl)pyridine-2-carboxamide (1)

Crystal data

C12H9N3O2	Dx = 1.449 Mg m^−3
Mr = 227.22	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pna21	Cell parameters from 4719 reflections
a = 16.2689 (6) Å	θ = 4.2–74.0°
b = 12.8086 (7) Å	µ = 0.85 mm^−1
c = 4.9983 (2) Å	T = 100 K
V = 1041.56 (8) Å^3	Block, clear colourless
Z = 4	0.20 × 0.12 × 0.06 mm
F(000) = 472

Data collection

SuperNova, Dual, Cu at zero, Atlas diffractometer	2028 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	1831 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.076
Detector resolution: 10.4839 pixels mm^-1	θmax = 75.3°, θmin = 4.4°
ω scans	h = −14→20
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2015)	k = −15→15
Tmin = 0.187, Tmax = 0.563	l = −5→6
8626 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.060	w = 1/[σ^2(Fo^2) + (0.1236P)^2 + 0.0215P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.170	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.32 e Å^−3
2028 reflections	Δρmin = −0.30 e Å^−3
157 parameters	Absolute structure: Flack x determined using 673 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.0 (3)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O1	0.29400 (14)	0.3937 (2)	0.2999 (6)	0.0362 (7)
O2	0.22855 (16)	0.2512 (2)	0.7000 (6)	0.0343 (7)
N1	0.10762 (18)	0.4562 (3)	−0.0277 (7)	0.0301 (7)
N2	0.16131 (17)	0.3339 (2)	0.3528 (7)	0.0299 (7)
N3	0.01890 (19)	0.2587 (3)	0.5153 (7)	0.0335 (8)
C1	0.1883 (2)	0.4642 (3)	0.0217 (8)	0.0288 (8)
C2	0.2393 (2)	0.5328 (3)	−0.1112 (8)	0.0322 (8)
H2A	0.296091	0.536690	−0.068626	0.039*
C3	0.2060 (2)	0.5956 (3)	−0.3071 (9)	0.0372 (9)
H3	0.239464	0.643907	−0.401515	0.045*
C4	0.1232 (2)	0.5872 (3)	−0.3640 (9)	0.0372 (9)
H4	0.098806	0.628601	−0.500275	0.045*
C5	0.0767 (2)	0.5170 (3)	−0.2176 (8)	0.0344 (8)
H5	0.019566	0.512061	−0.255151	0.041*
C6	0.2213 (2)	0.3943 (3)	0.2372 (8)	0.0279 (8)
C7	0.1662 (2)	0.2696 (3)	0.5753 (8)	0.0284 (8)
C8	0.0840 (2)	0.2245 (3)	0.6517 (8)	0.0290 (8)
C9	−0.0551 (2)	0.2220 (3)	0.5853 (10)	0.0361 (9)
H9	−0.101987	0.245492	0.489110	0.043*
C10	−0.0664 (2)	0.1513 (3)	0.7923 (9)	0.0371 (9)
H10	−0.119977	0.127904	0.838484	0.045*
C11	0.0010 (3)	0.1157 (4)	0.9290 (9)	0.0410 (10)
H11	−0.004963	0.066767	1.070577	0.049*
C12	0.0785 (2)	0.1526 (3)	0.8565 (9)	0.0368 (9)
H12	0.126414	0.128826	0.946242	0.044*
H2	0.110 (3)	0.341 (4)	0.286 (12)	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0224 (11)	0.0457 (15)	0.0404 (17)	0.0004 (11)	−0.0002 (11)	0.0017 (13)
O2	0.0291 (12)	0.0387 (14)	0.0352 (15)	0.0032 (10)	−0.0065 (10)	0.0041 (12)
N1	0.0235 (13)	0.0340 (15)	0.0328 (17)	0.0006 (11)	−0.0019 (12)	−0.0011 (13)
N2	0.0235 (13)	0.0350 (15)	0.0312 (17)	0.0004 (11)	−0.0032 (12)	0.0022 (13)
N3	0.0286 (14)	0.0353 (16)	0.0365 (19)	−0.0011 (11)	0.0011 (13)	0.0023 (15)
C1	0.0270 (15)	0.0290 (16)	0.0302 (19)	0.0025 (13)	0.0024 (14)	−0.0040 (14)
C2	0.0270 (16)	0.0333 (18)	0.036 (2)	−0.0007 (13)	0.0064 (15)	−0.0024 (16)
C3	0.0379 (19)	0.0334 (18)	0.040 (2)	0.0007 (15)	0.0100 (17)	0.0029 (17)
C4	0.0424 (19)	0.0361 (18)	0.033 (2)	0.0081 (17)	0.0016 (17)	−0.0015 (16)
C5	0.0308 (16)	0.0393 (18)	0.033 (2)	0.0036 (15)	0.0007 (16)	−0.0005 (17)
C6	0.0214 (15)	0.0318 (17)	0.0304 (19)	0.0016 (12)	−0.0011 (13)	−0.0024 (15)
C7	0.0303 (16)	0.0281 (16)	0.0269 (18)	0.0034 (13)	−0.0011 (14)	0.0002 (14)
C8	0.0283 (16)	0.0296 (17)	0.0292 (19)	0.0010 (13)	−0.0011 (13)	−0.0032 (15)
C9	0.0262 (16)	0.0390 (19)	0.043 (2)	−0.0019 (15)	0.0023 (16)	0.0022 (16)
C10	0.0350 (17)	0.0367 (18)	0.040 (2)	−0.0063 (15)	0.0072 (16)	−0.0006 (17)
C11	0.043 (2)	0.041 (2)	0.038 (3)	−0.0062 (16)	0.0010 (18)	0.0060 (18)
C12	0.0346 (17)	0.041 (2)	0.035 (2)	−0.0004 (15)	−0.0030 (15)	0.0069 (17)

Geometric parameters (Å, º)

O1—C6	1.224 (4)	C3—C4	1.380 (6)
O2—C7	1.214 (4)	C4—H4	0.9500
N1—C1	1.339 (4)	C4—C5	1.385 (6)
N1—C5	1.327 (5)	C5—H5	0.9500
N2—C6	1.373 (5)	C7—C8	1.506 (5)
N2—C7	1.385 (5)	C8—C12	1.380 (6)
N2—H2	0.90 (5)	C9—H9	0.9500
N3—C8	1.333 (5)	C9—C10	1.387 (6)
N3—C9	1.339 (5)	C10—H10	0.9500
C1—C2	1.379 (5)	C10—C11	1.370 (6)
C1—C6	1.499 (5)	C11—H11	0.9500
C2—H2A	0.9500	C11—C12	1.394 (6)
C2—C3	1.378 (6)	C12—H12	0.9500
C3—H3	0.9500
C5—N1—C1	117.3 (3)	O1—C6—C1	122.3 (3)
C6—N2—C7	129.2 (3)	N2—C6—C1	112.6 (3)
C6—N2—H2	116 (3)	O2—C7—N2	125.1 (3)
C7—N2—H2	114 (3)	O2—C7—C8	122.5 (3)
C8—N3—C9	117.8 (4)	N2—C7—C8	112.4 (3)
N1—C1—C2	123.3 (4)	N3—C8—C7	116.7 (3)
N1—C1—C6	115.9 (3)	N3—C8—C12	123.1 (4)
C2—C1—C6	120.7 (3)	C12—C8—C7	120.1 (3)
C1—C2—H2A	120.7	N3—C9—H9	118.6
C3—C2—C1	118.6 (3)	N3—C9—C10	122.9 (4)
C3—C2—H2A	120.7	C10—C9—H9	118.6
C2—C3—H3	120.5	C9—C10—H10	120.5
C2—C3—C4	119.0 (4)	C11—C10—C9	118.9 (4)
C4—C3—H3	120.5	C11—C10—H10	120.5
C3—C4—H4	120.8	C10—C11—H11	120.6
C3—C4—C5	118.3 (4)	C10—C11—C12	118.7 (4)
C5—C4—H4	120.8	C12—C11—H11	120.6
N1—C5—C4	123.5 (4)	C8—C12—C11	118.6 (4)
N1—C5—H5	118.3	C8—C12—H12	120.7
C4—C5—H5	118.3	C11—C12—H12	120.7
O1—C6—N2	125.1 (3)
O2—C7—C8—N3	173.6 (4)	C3—C4—C5—N1	−1.0 (6)
O2—C7—C8—C12	−5.5 (5)	C5—N1—C1—C2	1.0 (6)
N1—C1—C2—C3	−0.8 (6)	C5—N1—C1—C6	−179.9 (3)
N1—C1—C6—O1	179.4 (4)	C6—N2—C7—O2	−4.7 (6)
N1—C1—C6—N2	−1.1 (5)	C6—N2—C7—C8	174.7 (3)
N2—C7—C8—N3	−5.8 (5)	C6—C1—C2—C3	−179.8 (3)
N2—C7—C8—C12	175.2 (4)	C7—N2—C6—O1	7.6 (6)
N3—C8—C12—C11	−1.6 (6)	C7—N2—C6—C1	−171.9 (3)
N3—C9—C10—C11	−1.1 (7)	C7—C8—C12—C11	177.4 (4)
C1—N1—C5—C4	−0.1 (6)	C8—N3—C9—C10	0.3 (6)
C1—C2—C3—C4	−0.3 (6)	C9—N3—C8—C7	−178.0 (3)
C2—C1—C6—O1	−1.5 (5)	C9—N3—C8—C12	1.0 (6)
C2—C1—C6—N2	178.0 (3)	C9—C10—C11—C12	0.5 (7)
C2—C3—C4—C5	1.1 (6)	C10—C11—C12—C8	0.7 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1	0.90 (5)	2.15 (6)	2.614 (5)	111 (4)
N2—H2···N3	0.90 (5)	2.15 (5)	2.637 (4)	113 (5)
C3—H3···O2^i	0.95	2.48	3.343 (5)	152
C5—H5···N1^ii	0.95	2.51	3.393 (5)	154

Symmetry codes: (i) −x+1/2, y+1/2, z−3/2; (ii) −x, −y+1, z−1/2.

N-(3-Fluoropyridine-2-carbonyl)pyridine-2-carboxamide (2)

Crystal data

C12H8FN3O2	Dx = 1.546 Mg m^−3
Mr = 245.21	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pna21	Cell parameters from 2360 reflections
a = 16.6058 (10) Å	θ = 3.4–74.8°
b = 12.9096 (7) Å	µ = 1.03 mm^−1
c = 4.9153 (3) Å	T = 100 K
V = 1053.71 (11) Å^3	Block, clear colourless
Z = 4	0.26 × 0.10 × 0.05 mm
F(000) = 504

Data collection

SuperNova, Dual, Cu at zero, Atlas diffractometer	1798 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	1567 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.054
Detector resolution: 10.4839 pixels mm^-1	θmax = 75.9°, θmin = 5.3°
ω scans	h = −19→20
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2015)	k = −15→16
Tmin = 0.983, Tmax = 0.995	l = −6→5
5774 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.055	w = 1/[σ^2(Fo^2) + (0.0898P)^2 + 0.4172P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.152	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.28 e Å^−3
1798 reflections	Δρmin = −0.28 e Å^−3
176 parameters	Absolute structure: Flack x determined using 450 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.2 (3)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O2	0.27904 (19)	0.7427 (2)	0.1952 (8)	0.0338 (8)
O1	0.21184 (17)	0.8809 (3)	0.5995 (8)	0.0359 (8)
N3	0.4847 (2)	0.7588 (3)	0.3876 (9)	0.0309 (9)
N2	0.3438 (2)	0.8296 (3)	0.5407 (9)	0.0271 (8)
N1	0.3932 (2)	0.9540 (3)	0.9257 (8)	0.0269 (8)
C12	0.4327 (3)	0.6517 (4)	0.0372 (11)	0.0407 (12)
H12	0.387317	0.626086	−0.059309	0.049*	0.563 (8)
C8	0.4221 (3)	0.7223 (3)	0.2426 (10)	0.0267 (9)
C9	0.5586 (3)	0.7247 (3)	0.3242 (12)	0.0358 (11)
H9	0.603043	0.749297	0.427390	0.043*
C10	0.5730 (3)	0.6555 (4)	0.1156 (11)	0.0393 (11)
H10	0.626396	0.634525	0.073279	0.047*
C11	0.5087 (3)	0.6176 (4)	−0.0299 (12)	0.0433 (13)
H11	0.516473	0.569153	−0.172922	0.052*
C7	0.3403 (2)	0.7643 (3)	0.3213 (10)	0.0270 (9)
C6	0.2827 (2)	0.8864 (3)	0.6609 (9)	0.0257 (9)
C1	0.3139 (2)	0.9587 (3)	0.8767 (10)	0.0247 (9)
C2	0.2642 (3)	1.0262 (3)	1.0150 (10)	0.0300 (10)
H2A	0.208315	1.028822	0.973723	0.036*	0.437 (8)
C3	0.2959 (3)	1.0902 (3)	1.2140 (12)	0.0351 (11)
H3	0.262391	1.137086	1.310847	0.042*
C4	0.3766 (3)	1.0842 (3)	1.2677 (11)	0.0341 (10)
H4	0.400053	1.126025	1.405499	0.041*
C5	0.4234 (3)	1.0164 (3)	1.1188 (10)	0.0302 (9)
H5	0.479609	1.013741	1.154679	0.036*
F1B	0.3801 (4)	0.6170 (5)	−0.1240 (16)	0.046 (2)	0.437 (8)
F1A	0.1855 (3)	1.0352 (3)	0.9733 (12)	0.0368 (16)	0.563 (8)
H2	0.395 (3)	0.837 (4)	0.611 (14)	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0306 (15)	0.0302 (14)	0.0407 (19)	−0.0041 (12)	−0.0077 (16)	−0.0028 (15)
O1	0.0223 (15)	0.0426 (17)	0.043 (2)	−0.0018 (12)	−0.0037 (15)	0.0012 (16)
N3	0.0279 (18)	0.0288 (17)	0.036 (2)	−0.0004 (13)	−0.0008 (17)	−0.0003 (17)
N2	0.0239 (17)	0.0283 (17)	0.029 (2)	−0.0004 (13)	−0.0022 (15)	−0.0039 (15)
N1	0.0249 (17)	0.0281 (16)	0.028 (2)	−0.0030 (13)	−0.0019 (15)	−0.0021 (15)
C12	0.055 (3)	0.034 (2)	0.033 (3)	0.006 (2)	−0.009 (3)	−0.003 (2)
C8	0.029 (2)	0.0221 (16)	0.029 (2)	−0.0005 (14)	−0.0027 (18)	0.0019 (17)
C9	0.033 (2)	0.028 (2)	0.047 (3)	0.0026 (17)	0.003 (2)	−0.001 (2)
C10	0.045 (2)	0.030 (2)	0.043 (3)	0.0102 (19)	0.012 (2)	0.005 (2)
C11	0.061 (3)	0.036 (2)	0.033 (3)	0.010 (2)	0.004 (3)	−0.004 (2)
C7	0.031 (2)	0.0227 (18)	0.027 (2)	−0.0036 (15)	−0.003 (2)	0.0033 (17)
C6	0.0198 (18)	0.0282 (18)	0.029 (3)	−0.0029 (15)	−0.0016 (17)	0.0038 (19)
C1	0.0218 (18)	0.0222 (16)	0.030 (2)	−0.0014 (14)	−0.0005 (19)	0.0011 (16)
C2	0.028 (2)	0.0232 (18)	0.039 (3)	0.0010 (15)	0.006 (2)	0.0045 (19)
C3	0.043 (3)	0.0250 (19)	0.037 (3)	−0.0003 (17)	0.009 (2)	−0.003 (2)
C4	0.044 (3)	0.0276 (19)	0.030 (2)	−0.0053 (18)	0.005 (2)	−0.002 (2)
C5	0.030 (2)	0.0301 (19)	0.031 (2)	−0.0040 (16)	−0.001 (2)	−0.002 (2)
F1B	0.036 (4)	0.053 (4)	0.050 (5)	−0.002 (3)	−0.012 (3)	−0.025 (4)
F1A	0.020 (2)	0.028 (2)	0.062 (4)	0.0007 (16)	0.002 (2)	0.001 (2)

Geometric parameters (Å, º)

O2—C7	1.224 (5)	C9—C10	1.381 (7)
O1—C6	1.217 (5)	C10—H10	0.9500
N3—C8	1.346 (6)	C10—C11	1.376 (8)
N3—C9	1.340 (6)	C11—H11	0.9500
N2—C7	1.370 (6)	C6—C1	1.505 (6)
N2—C6	1.384 (6)	C1—C2	1.380 (6)
N2—H2	0.92 (6)	C2—H2A	0.9500
N1—C1	1.341 (5)	C2—C3	1.384 (7)
N1—C5	1.342 (6)	C2—F1A	1.327 (6)
C12—H12	0.9500	C3—H3	0.9500
C12—C8	1.372 (7)	C3—C4	1.369 (7)
C12—C11	1.376 (7)	C4—H4	0.9500
C12—F1B	1.262 (8)	C4—C5	1.381 (6)
C8—C7	1.511 (6)	C5—H5	0.9500
C9—H9	0.9500
C9—N3—C8	118.0 (4)	O2—C7—C8	122.4 (4)
C7—N2—C6	129.1 (4)	N2—C7—C8	112.6 (3)
C7—N2—H2	113 (4)	O1—C6—N2	124.9 (4)
C6—N2—H2	118 (4)	O1—C6—C1	122.9 (4)
C1—N1—C5	117.9 (4)	N2—C6—C1	112.2 (3)
C8—C12—H12	119.8	N1—C1—C6	115.9 (3)
C8—C12—C11	120.5 (5)	N1—C1—C2	121.9 (4)
C11—C12—H12	119.8	C2—C1—C6	122.2 (4)
F1B—C12—C8	127.5 (6)	C1—C2—H2A	120.1
F1B—C12—C11	111.7 (6)	C1—C2—C3	119.8 (4)
N3—C8—C12	121.5 (4)	C3—C2—H2A	120.1
N3—C8—C7	115.7 (4)	F1A—C2—C1	124.6 (5)
C12—C8—C7	122.8 (4)	F1A—C2—C3	115.6 (4)
N3—C9—H9	118.5	C2—C3—H3	120.8
N3—C9—C10	122.9 (5)	C4—C3—C2	118.4 (4)
C10—C9—H9	118.5	C4—C3—H3	120.8
C9—C10—H10	120.6	C3—C4—H4	120.5
C11—C10—C9	118.8 (5)	C3—C4—C5	119.0 (4)
C11—C10—H10	120.6	C5—C4—H4	120.5
C12—C11—H11	120.9	N1—C5—C4	123.0 (4)
C10—C11—C12	118.3 (5)	N1—C5—H5	118.5
C10—C11—H11	120.9	C4—C5—H5	118.5
O2—C7—N2	125.0 (4)
O1—C6—C1—N1	178.5 (4)	C11—C12—C8—C7	178.6 (4)
O1—C6—C1—C2	−1.9 (7)	C7—N2—C6—O1	6.0 (7)
N3—C8—C7—O2	175.2 (4)	C7—N2—C6—C1	−172.9 (4)
N3—C8—C7—N2	−3.2 (5)	C6—N2—C7—O2	−2.1 (7)
N3—C9—C10—C11	−1.7 (8)	C6—N2—C7—C8	176.3 (4)
N2—C6—C1—N1	−2.6 (5)	C6—C1—C2—C3	179.2 (4)
N2—C6—C1—C2	177.0 (4)	C6—C1—C2—F1A	−0.4 (7)
N1—C1—C2—C3	−1.2 (7)	C1—N1—C5—C4	0.2 (6)
N1—C1—C2—F1A	179.2 (4)	C1—C2—C3—C4	0.0 (7)
C12—C8—C7—O2	−4.7 (6)	C2—C3—C4—C5	1.2 (7)
C12—C8—C7—N2	176.8 (4)	C3—C4—C5—N1	−1.3 (7)
C8—N3—C9—C10	1.0 (7)	C5—N1—C1—C6	−179.3 (4)
C8—C12—C11—C10	0.6 (8)	C5—N1—C1—C2	1.1 (6)
C9—N3—C8—C12	0.6 (7)	F1B—C12—C8—N3	−175.0 (6)
C9—N3—C8—C7	−179.4 (4)	F1B—C12—C8—C7	5.0 (9)
C9—C10—C11—C12	0.9 (7)	F1B—C12—C11—C10	175.1 (6)
C11—C12—C8—N3	−1.3 (7)	F1A—C2—C3—C4	179.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1	0.92 (5)	2.16 (6)	2.614 (6)	109 (4)
N2—H2···N3	0.92 (5)	2.11 (6)	2.622 (5)	114 (5)
C3—H3···O2^i	0.95	2.43	3.320 (6)	156
C3—H3···F1B^i	0.95	2.40	3.049 (8)	125
C5—H5···N1^ii	0.95	2.53	3.420 (6)	156
C10—H10···F1A^iii	0.95	2.45	3.169 (7)	132

Symmetry codes: (i) −x+1/2, y+1/2, z+3/2; (ii) −x+1, −y+2, z+1/2; (iii) x+1/2, −y+3/2, z−1.

3-Fluoro-N-(3-fluoropyridine-2-carbonyl)pyridine-2-carboxamide (3)

Crystal data

C12H7F2N3O2	F(000) = 536
Mr = 263.21	Dx = 1.660 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 6.7062 (3) Å	Cell parameters from 1899 reflections
b = 14.1190 (5) Å	θ = 5.0–74.9°
c = 11.2074 (5) Å	µ = 1.22 mm^−1
β = 97.140 (4)°	T = 100 K
V = 1052.94 (8) Å^3	Block, clear colourless
Z = 4	0.11 × 0.09 × 0.06 mm

Data collection

SuperNova, Dual, Cu at zero, Atlas diffractometer	1083 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	856 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.069
Detector resolution: 10.4839 pixels mm^-1	θmax = 75.4°, θmin = 5.1°
ω scans	h = −7→8
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2015)	k = −17→17
Tmin = 0.993, Tmax = 0.996	l = −14→13
5200 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.161	w = 1/[σ^2(Fo^2) + (0.0954P)^2 + 0.7955P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1083 reflections	Δρmax = 0.29 e Å^−3
88 parameters	Δρmin = −0.32 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
F1	0.1012 (3)	0.49942 (9)	0.14190 (14)	0.0349 (5)
O1	0.1649 (3)	0.53996 (11)	0.37977 (16)	0.0296 (5)
N1	0.0596 (3)	0.29674 (13)	0.33292 (17)	0.0204 (5)
N2	0.250000	0.41071 (19)	0.500000	0.0218 (6)
C2	0.0612 (4)	0.41086 (16)	0.1771 (2)	0.0245 (6)
C1	0.0945 (3)	0.38567 (15)	0.2979 (2)	0.0217 (5)
C5	−0.0104 (3)	0.23375 (15)	0.2494 (2)	0.0208 (5)
H5	−0.037842	0.171355	0.274533	0.025*
C4	−0.0453 (3)	0.25475 (16)	0.1273 (2)	0.0233 (5)
H4	−0.094044	0.207588	0.070604	0.028*
C3	−0.0075 (4)	0.34557 (16)	0.0902 (2)	0.0247 (6)
H3	−0.028177	0.362470	0.007558	0.030*
C6	0.1711 (3)	0.45473 (15)	0.3944 (2)	0.0213 (5)
H2	0.250000	0.351 (3)	0.500000	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0551 (11)	0.0191 (7)	0.0292 (9)	−0.0062 (6)	−0.0002 (7)	0.0071 (6)
O1	0.0404 (10)	0.0157 (8)	0.0316 (10)	0.0016 (7)	0.0006 (8)	0.0023 (7)
N1	0.0190 (9)	0.0171 (9)	0.0254 (10)	0.0017 (7)	0.0038 (7)	0.0014 (7)
N2	0.0254 (13)	0.0141 (12)	0.0262 (15)	0.000	0.0042 (11)	0.000
C2	0.0262 (11)	0.0165 (10)	0.0309 (13)	0.0012 (9)	0.0042 (10)	0.0048 (9)
C1	0.0203 (11)	0.0167 (11)	0.0278 (12)	0.0022 (8)	0.0023 (9)	0.0021 (9)
C5	0.0188 (10)	0.0174 (10)	0.0270 (12)	0.0007 (8)	0.0058 (9)	0.0008 (8)
C4	0.0213 (11)	0.0223 (11)	0.0258 (12)	0.0025 (8)	0.0014 (9)	−0.0022 (9)
C3	0.0276 (11)	0.0239 (12)	0.0222 (12)	0.0039 (9)	0.0014 (10)	0.0028 (9)
C6	0.0222 (11)	0.0162 (10)	0.0259 (12)	0.0014 (8)	0.0051 (9)	0.0009 (9)

Geometric parameters (Å, º)

F1—C2	1.348 (2)	C2—C3	1.378 (3)
O1—C6	1.214 (3)	C1—C6	1.498 (3)
N1—C1	1.344 (3)	C5—H5	0.9500
N1—C5	1.334 (3)	C5—C4	1.391 (3)
N2—C6^i	1.383 (3)	C4—H4	0.9500
N2—C6	1.383 (3)	C4—C3	1.381 (3)
N2—H2	0.85 (4)	C3—H3	0.9500
C2—C1	1.391 (3)
C5—N1—C1	118.5 (2)	N1—C5—C4	123.4 (2)
C6^i—N2—C6	126.6 (3)	C4—C5—H5	118.3
C6^i—N2—H2	116.71 (13)	C5—C4—H4	120.7
C6—N2—H2	116.71 (13)	C3—C4—C5	118.6 (2)
F1—C2—C1	120.5 (2)	C3—C4—H4	120.7
F1—C2—C3	118.4 (2)	C2—C3—C4	117.8 (2)
C3—C2—C1	121.1 (2)	C2—C3—H3	121.1
N1—C1—C2	120.7 (2)	C4—C3—H3	121.1
N1—C1—C6	117.0 (2)	O1—C6—N2	124.3 (2)
C2—C1—C6	122.3 (2)	O1—C6—C1	123.0 (2)
N1—C5—H5	118.3	N2—C6—C1	112.68 (19)
F1—C2—C1—N1	−178.3 (2)	C1—C2—C3—C4	1.0 (4)
F1—C2—C1—C6	1.3 (4)	C5—N1—C1—C2	−1.0 (3)
F1—C2—C3—C4	179.1 (2)	C5—N1—C1—C6	179.41 (19)
N1—C1—C6—O1	−162.6 (2)	C5—C4—C3—C2	−0.6 (3)
N1—C1—C6—N2	17.9 (3)	C3—C2—C1—N1	−0.2 (4)
N1—C5—C4—C3	−0.6 (3)	C3—C2—C1—C6	179.3 (2)
C2—C1—C6—O1	17.8 (4)	C6^i—N2—C6—O1	1.68 (18)
C2—C1—C6—N2	−161.7 (2)	C6^i—N2—C6—C1	−178.8 (2)
C1—N1—C5—C4	1.4 (3)

Symmetry code: (i) −x+1/2, y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1	0.84 (4)	2.27 (2)	2.671 (2)	110 (1)
N2—H2···N1^i	0.84 (4)	2.27 (2)	2.671 (2)	110 (1)
C4—H4···O1^ii	0.95	2.49	3.135 (3)	125
C5—H5···O1^ii	0.95	2.61	3.207 (3)	122
C3—H3···F1^iii	0.95	2.58	3.398 (3)	145
C5—H5···F1^ii	0.95	2.66	3.604 (3)	176

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