2-Amino­pyridinium isonicotinate 2-amino­pyridine

In the title compound, C₅H₇N₂⁺·C₆H₄NO₂⁻·C₅H₆N₂, the components are linked into a two-dimensional network through N—H...O and N—H...N hydrogen bonds. Adjacent layers are further linked by C—H...O hydrogen bonds, forming a three-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.055
• wR factor = 0.163
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              C5 H6 N2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

2-Aminopyridinium isonicotinate 2-aminopyridine

Crystal data

C5H7N2^+·C6H4NO2^−·C5H6N2	F(000) = 656
Mr = 311.35	Dx = 1.285 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2442 reflections
a = 5.6204 (11) Å	θ = 2.4–23.0°
b = 25.623 (5) Å	µ = 0.09 mm^−1
c = 11.256 (2) Å	T = 298 K
β = 96.748 (4)°	Block, colourless
V = 1609.8 (5) Å^3	0.23 × 0.20 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3733 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	2478 reflections with I > 2/s(I)
Graphite monochromator	Rint = 0.032
0.3° wide ω exposures scans	θmax = 27.7°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −7→7
Tmin = 0.980, Tmax = 0.991	k = −33→28
9742 measured reflections	l = −12→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0813P)^2 + 0.0566P] where P = (Fo^2 + 2Fc^2)/3
3733 reflections	(Δ/σ)max = 0.001
223 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

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

	x	y	z	Uiso*/Ueq
C1	0.9083 (3)	0.15232 (6)	0.72318 (14)	0.0438 (4)
C2	1.0746 (3)	0.14047 (8)	0.64718 (16)	0.0543 (5)
H2	1.0631	0.1550	0.5710	0.065*
C3	1.2595 (4)	0.10666 (8)	0.68562 (19)	0.0621 (5)
H3	1.3737	0.1000	0.6341	0.075*
C4	1.1194 (4)	0.09414 (7)	0.86243 (18)	0.0580 (5)
H4	1.1305	0.0777	0.9365	0.070*
C5	0.9329 (3)	0.12833 (7)	0.83382 (15)	0.0495 (5)
H5	0.8246	0.1352	0.8883	0.059*
C6	0.7074 (3)	0.19016 (7)	0.68586 (14)	0.0443 (4)
C7	0.1515 (3)	0.28508 (7)	0.59176 (15)	0.0465 (4)
C8	−0.0460 (4)	0.31845 (8)	0.56919 (18)	0.0597 (5)
H8	−0.1069	0.3262	0.4908	0.072*
C9	−0.1482 (4)	0.33935 (8)	0.6607 (2)	0.0699 (6)
H9	−0.2815	0.3609	0.6451	0.084*
C10	−0.0545 (4)	0.32879 (9)	0.7794 (2)	0.0698 (6)
H10	−0.1221	0.3436	0.8430	0.084*
C11	0.1341 (4)	0.29690 (8)	0.79898 (17)	0.0586 (5)
H11	0.1974	0.2893	0.8771	0.070*
N1	1.2844 (3)	0.08313 (7)	0.79116 (16)	0.0612 (5)
N2	0.2344 (3)	0.27557 (6)	0.70708 (12)	0.0485 (4)
H2A	0.375 (4)	0.2547 (8)	0.7196 (17)	0.058*
N3	0.2600 (4)	0.26245 (7)	0.50760 (14)	0.0602 (5)
H3A	0.206 (4)	0.2713 (8)	0.431 (2)	0.072*
H3B	0.400 (4)	0.2426 (9)	0.5262 (19)	0.072*
O1	0.6588 (3)	0.19897 (6)	0.57809 (11)	0.0690 (4)
O2	0.6016 (2)	0.21011 (5)	0.76763 (10)	0.0530 (4)
N5	1.6831 (3)	0.00617 (7)	0.89797 (17)	0.0602 (5)
H5A	1.751 (5)	0.0152 (10)	0.973 (2)	0.072*
H5B	1.570 (5)	0.0261 (11)	0.874 (2)	0.072*
C12	1.8092 (3)	−0.01488 (7)	0.81547 (16)	0.0481 (4)
C13	1.7243 (4)	−0.01425 (9)	0.69368 (18)	0.0655 (6)
H13	1.5800	0.0020	0.6670	0.079*
C14	1.8550 (5)	−0.03767 (11)	0.6150 (2)	0.0826 (7)
H14	1.8007	−0.0376	0.5337	0.099*
N4	2.0184 (3)	−0.03766 (6)	0.85612 (13)	0.0533 (4)
C15	2.0706 (5)	−0.06184 (11)	0.6562 (2)	0.0823 (7)
H15	2.1629	−0.0784	0.6041	0.099*
C16	2.1401 (4)	−0.06026 (9)	0.7752 (2)	0.0672 (6)
H16	2.2846	−0.0762	0.8030	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0508 (10)	0.0390 (9)	0.0389 (9)	−0.0036 (8)	−0.0064 (7)	−0.0018 (7)
C2	0.0556 (11)	0.0577 (12)	0.0485 (10)	0.0004 (9)	0.0017 (8)	0.0038 (9)
C3	0.0554 (12)	0.0594 (13)	0.0720 (14)	0.0035 (10)	0.0091 (10)	−0.0050 (10)
C4	0.0707 (13)	0.0458 (11)	0.0532 (11)	0.0019 (10)	−0.0112 (10)	0.0058 (9)
C5	0.0594 (11)	0.0449 (10)	0.0425 (10)	0.0017 (9)	−0.0017 (8)	0.0020 (7)
C6	0.0470 (10)	0.0482 (10)	0.0355 (9)	0.0004 (8)	−0.0049 (7)	0.0023 (7)
C7	0.0549 (11)	0.0448 (10)	0.0379 (9)	−0.0011 (8)	−0.0024 (8)	0.0046 (7)
C8	0.0657 (13)	0.0534 (12)	0.0574 (12)	0.0099 (10)	−0.0031 (10)	0.0079 (9)
C9	0.0665 (14)	0.0541 (13)	0.0902 (17)	0.0117 (11)	0.0145 (12)	0.0055 (11)
C10	0.0849 (16)	0.0581 (13)	0.0713 (15)	0.0025 (12)	0.0295 (12)	−0.0079 (11)
C11	0.0773 (14)	0.0571 (12)	0.0423 (10)	−0.0046 (11)	0.0113 (9)	−0.0032 (8)
N1	0.0575 (10)	0.0491 (10)	0.0725 (11)	0.0028 (8)	−0.0108 (9)	0.0007 (8)
N2	0.0605 (10)	0.0504 (9)	0.0338 (7)	0.0053 (8)	0.0019 (7)	0.0026 (6)
N3	0.0763 (12)	0.0702 (12)	0.0320 (8)	0.0219 (9)	−0.0023 (8)	0.0060 (7)
O1	0.0802 (10)	0.0911 (11)	0.0342 (7)	0.0295 (8)	0.0006 (6)	0.0123 (6)
O2	0.0637 (8)	0.0575 (8)	0.0349 (6)	0.0126 (6)	−0.0065 (6)	−0.0036 (5)
N5	0.0511 (10)	0.0713 (12)	0.0572 (10)	0.0137 (9)	0.0019 (8)	0.0003 (9)
C12	0.0440 (10)	0.0447 (10)	0.0543 (11)	−0.0028 (8)	0.0013 (8)	0.0047 (8)
C13	0.0614 (13)	0.0746 (15)	0.0568 (12)	−0.0016 (11)	−0.0081 (10)	0.0025 (10)
C14	0.0909 (19)	0.105 (2)	0.0505 (13)	−0.0094 (16)	0.0016 (12)	−0.0121 (12)
N4	0.0477 (9)	0.0541 (10)	0.0575 (9)	0.0065 (7)	0.0031 (7)	0.0021 (7)
C15	0.0780 (17)	0.0950 (19)	0.0769 (16)	−0.0028 (15)	0.0227 (13)	−0.0259 (13)
C16	0.0536 (12)	0.0665 (14)	0.0820 (16)	0.0065 (10)	0.0100 (11)	−0.0083 (11)

Geometric parameters (Å, º)

C1—C2	1.373 (2)	C10—C11	1.336 (3)
C1—C5	1.381 (2)	C10—H10	0.9300
C1—C6	1.510 (2)	C11—N2	1.350 (2)
C2—C3	1.383 (3)	C11—H11	0.9300
C2—H2	0.9300	N2—H2A	0.95 (2)
C3—N1	1.325 (3)	N3—H3A	0.91 (2)
C3—H3	0.9300	N3—H3B	0.94 (2)
C4—N1	1.326 (3)	N5—C12	1.346 (2)
C4—C5	1.375 (3)	N5—H5A	0.92 (3)
C4—H4	0.9300	N5—H5B	0.84 (3)
C5—H5	0.9300	C12—N4	1.344 (2)
C6—O1	1.2326 (19)	C12—C13	1.398 (3)
C6—O2	1.2612 (19)	C13—C14	1.356 (3)
C7—N3	1.320 (2)	C13—H13	0.9300
C7—N2	1.349 (2)	C14—C15	1.391 (4)
C7—C8	1.401 (3)	C14—H14	0.9300
C8—C9	1.348 (3)	N4—C16	1.334 (2)
C8—H8	0.9300	C15—C16	1.351 (3)
C9—C10	1.404 (3)	C15—H15	0.9300
C9—H9	0.9300	C16—H16	0.9300
C2—C1—C5	117.39 (17)	C10—C11—N2	121.06 (19)
C2—C1—C6	120.67 (15)	C10—C11—H11	119.5
C5—C1—C6	121.93 (16)	N2—C11—H11	119.5
C1—C2—C3	119.02 (17)	C3—N1—C4	115.98 (17)
C1—C2—H2	120.5	C7—N2—C11	122.42 (17)
C3—C2—H2	120.5	C7—N2—H2A	115.6 (11)
N1—C3—C2	124.19 (19)	C11—N2—H2A	121.9 (11)
N1—C3—H3	117.9	C7—N3—H3A	116.3 (13)
C2—C3—H3	117.9	C7—N3—H3B	121.6 (13)
N1—C4—C5	124.19 (18)	H3A—N3—H3B	121.4 (18)
N1—C4—H4	117.9	C6—O1—H3B	119.4 (6)
C5—C4—H4	117.9	C12—N5—H5A	123.0 (16)
C4—C5—C1	119.17 (18)	C12—N5—H5B	117.4 (16)
C4—C5—H5	120.4	H5A—N5—H5B	111 (2)
C1—C5—H5	120.4	N4—C12—N5	116.74 (17)
O1—C6—O2	125.11 (16)	N4—C12—C13	121.55 (18)
O1—C6—C1	117.60 (15)	N5—C12—C13	121.69 (18)
O2—C6—C1	117.29 (14)	C14—C13—C12	119.1 (2)
N3—C7—N2	118.36 (17)	C14—C13—H13	120.4
N3—C7—C8	124.14 (17)	C12—C13—H13	120.4
N2—C7—C8	117.50 (17)	C13—C14—C15	119.8 (2)
C9—C8—C7	120.24 (19)	C13—C14—H14	120.1
C9—C8—H8	119.9	C15—C14—H14	120.1
C7—C8—H8	119.9	C16—N4—C12	117.03 (17)
C8—C9—C10	120.3 (2)	C16—C15—C14	117.2 (2)
C8—C9—H9	119.8	C16—C15—H15	121.4
C10—C9—H9	119.8	C14—C15—H15	121.4
C11—C10—C9	118.44 (19)	N4—C16—C15	125.3 (2)
C11—C10—H10	120.8	N4—C16—H16	117.3
C9—C10—H10	120.8	C15—C16—H16	117.3
C5—C1—C2—C3	−1.7 (3)	C2—C3—N1—C4	−0.7 (3)
C6—C1—C2—C3	178.38 (16)	C5—C4—N1—C3	−1.2 (3)
C1—C2—C3—N1	2.2 (3)	N3—C7—N2—C11	−179.81 (18)
N1—C4—C5—C1	1.6 (3)	C8—C7—N2—C11	0.0 (3)
C2—C1—C5—C4	−0.1 (3)	C10—C11—N2—C7	0.1 (3)
C6—C1—C5—C4	179.86 (16)	O2—C6—O1—H3B	−3.0 (8)
C2—C1—C6—O1	19.0 (3)	C1—C6—O1—H3B	176.6 (8)
C5—C1—C6—O1	−160.97 (18)	N4—C12—C13—C14	0.7 (3)
C2—C1—C6—O2	−161.34 (16)	N5—C12—C13—C14	−177.7 (2)
C5—C1—C6—O2	18.7 (3)	C12—C13—C14—C15	−0.1 (4)
N3—C7—C8—C9	179.1 (2)	N5—C12—N4—C16	177.63 (17)
N2—C7—C8—C9	−0.7 (3)	C13—C12—N4—C16	−0.8 (3)
C7—C8—C9—C10	1.4 (3)	C13—C14—C15—C16	−0.4 (4)
C8—C9—C10—C11	−1.3 (3)	C12—N4—C16—C15	0.3 (3)
C9—C10—C11—N2	0.6 (3)	C14—C15—C16—N4	0.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.95 (2)	1.75 (2)	2.685 (2)	167.4 (17)
N3—H3B···O1	0.94 (2)	1.87 (2)	2.808 (2)	172.6 (19)
N5—H5B···N1	0.84 (3)	2.29 (3)	3.118 (3)	174 (2)
N3—H3A···O2^i	0.91 (2)	1.92 (2)	2.832 (2)	178 (2)
N5—H5A···N4^ii	0.92 (3)	2.26 (3)	3.168 (3)	169 (2)
C11—H11···O1^iii	0.93	2.32	3.130 (2)	146

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+4, −y, −z+2; (iii) x−1/2, −y+1/2, z+1/2.