3-Amino­pyridinium 2,4-dihydroxy­benzoate: a three-dimensional supra­molecular adduct assembled via hydrogen bonds

In the title salt, C₅H₇N₂⁺·C₇H₅O₄⁻,anions are linked through O—H...O hydrogen bonds into an infinite C₂²(16) chain parallel to the [010] direction. Adjacent chains are further organized into a three-dimensional supra­molecular structure based on N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.114
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C7 H5 O4

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

   2 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: PLATON.

3-aminopyridinium 2,4-dihydroxybenzoate

Crystal data

C5H7N2^+·C7H5O4^−	F(000) = 520
Mr = 248.24	Dx = 1.418 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4131 reflections
a = 11.7788 (15) Å	θ = 3.0–28.0°
b = 8.5808 (11) Å	µ = 0.11 mm^−1
c = 12.3340 (16) Å	T = 296 K
β = 111.113 (2)°	Block, yellow
V = 1162.9 (3) Å^3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer	2286 independent reflections
Radiation source: fine-focus sealed tube	2044 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −14→11
Tmin = 0.968, Tmax = 0.979	k = −10→10
8507 measured reflections	l = −15→15

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0671P)^2 + 0.1693P] where P = (Fo^2 + 2Fc^2)/3
2286 reflections	(Δ/σ)max = 0.001
177 parameters	Δρmax = 0.20 e Å^−3
3 restraints	Δρmin = −0.21 e Å^−3

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

	x	y	z	Uiso*/Ueq
C1	0.93717 (11)	1.04675 (13)	1.24661 (10)	0.0340 (3)
C2	1.02462 (11)	1.09169 (16)	1.35365 (11)	0.0408 (3)
C3	0.99288 (13)	1.18526 (17)	1.42994 (11)	0.0472 (3)
H3	1.0513	1.2132	1.5010	0.057*
C4	0.87487 (12)	1.23690 (15)	1.40050 (10)	0.0391 (3)
C5	0.78723 (12)	1.19841 (14)	1.29285 (11)	0.0386 (3)
H5A	0.7081	1.2360	1.2718	0.046*
C6	0.81927 (11)	1.10462 (14)	1.21864 (10)	0.0368 (3)
H6	0.7605	1.0786	1.1472	0.044*
C7	0.96975 (11)	0.94251 (14)	1.16599 (11)	0.0368 (3)
C8	0.87630 (12)	0.67694 (14)	0.84055 (11)	0.0386 (3)
H8	0.7985	0.7171	0.8237	0.046*
C9	0.89967 (12)	0.57732 (15)	0.76250 (11)	0.0383 (3)
C10	1.01906 (13)	0.52396 (16)	0.79214 (12)	0.0435 (3)
H10	1.0387	0.4584	0.7415	0.052*
C11	1.10741 (13)	0.56677 (16)	0.89465 (12)	0.0454 (3)
H11	1.1866	0.5303	0.9136	0.054*
C12	1.07871 (13)	0.66387 (15)	0.96959 (11)	0.0436 (3)
H12	1.1378	0.6930	1.0399	0.052*
N1	0.96540 (10)	0.71533 (12)	0.93997 (9)	0.0392 (3)
N2	0.81077 (13)	0.53484 (18)	0.66170 (12)	0.0620 (4)
H2A	0.7370 (9)	0.5588 (19)	0.6499 (14)	0.053 (4)*
H1	0.9430 (15)	0.7780 (16)	0.9841 (13)	0.056 (4)*
H2B	0.8316 (17)	0.478 (2)	0.6148 (14)	0.074 (6)*
O1	0.88626 (8)	0.89919 (11)	1.07278 (7)	0.0447 (3)
O2	1.07829 (9)	0.89982 (13)	1.19233 (9)	0.0537 (3)
O3	1.14156 (9)	1.04575 (15)	1.38534 (9)	0.0645 (3)
H3A	1.1490	0.9879	1.3354	0.097*
O4	0.84603 (10)	1.32595 (13)	1.47787 (8)	0.0545 (3)
H4	0.7726	1.3426	1.4530	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0353 (6)	0.0359 (6)	0.0335 (6)	−0.0019 (5)	0.0158 (5)	−0.0010 (4)
C2	0.0340 (7)	0.0480 (7)	0.0391 (7)	0.0035 (5)	0.0114 (5)	−0.0021 (5)
C3	0.0424 (8)	0.0602 (8)	0.0332 (6)	0.0006 (6)	0.0067 (5)	−0.0093 (6)
C4	0.0454 (7)	0.0405 (6)	0.0356 (6)	−0.0003 (5)	0.0197 (5)	−0.0049 (5)
C5	0.0332 (6)	0.0421 (6)	0.0423 (6)	0.0006 (5)	0.0159 (5)	−0.0046 (5)
C6	0.0333 (6)	0.0417 (6)	0.0351 (6)	−0.0032 (5)	0.0120 (5)	−0.0057 (5)
C7	0.0381 (7)	0.0389 (6)	0.0384 (6)	−0.0007 (5)	0.0197 (5)	−0.0003 (5)
C8	0.0368 (7)	0.0406 (6)	0.0422 (7)	−0.0002 (5)	0.0187 (6)	−0.0039 (5)
C9	0.0380 (7)	0.0418 (6)	0.0361 (6)	−0.0043 (5)	0.0145 (5)	−0.0053 (5)
C10	0.0453 (7)	0.0452 (7)	0.0452 (7)	0.0025 (5)	0.0223 (6)	−0.0088 (6)
C11	0.0366 (7)	0.0482 (7)	0.0501 (7)	0.0036 (5)	0.0141 (6)	−0.0001 (6)
C12	0.0453 (8)	0.0462 (7)	0.0356 (6)	−0.0064 (6)	0.0101 (6)	−0.0020 (5)
N1	0.0493 (6)	0.0380 (6)	0.0355 (5)	−0.0045 (5)	0.0215 (5)	−0.0063 (4)
N2	0.0422 (7)	0.0864 (10)	0.0516 (8)	−0.0013 (7)	0.0099 (6)	−0.0303 (7)
O1	0.0434 (5)	0.0553 (6)	0.0389 (5)	−0.0018 (4)	0.0190 (4)	−0.0133 (4)
O2	0.0400 (5)	0.0681 (7)	0.0557 (6)	0.0087 (4)	0.0205 (5)	−0.0128 (5)
O3	0.0365 (6)	0.0906 (9)	0.0557 (6)	0.0151 (5)	0.0039 (5)	−0.0207 (6)
O4	0.0542 (6)	0.0675 (7)	0.0423 (5)	0.0095 (5)	0.0180 (5)	−0.0173 (5)

Geometric parameters (Å, º)

C1—C6	1.3961 (17)	C8—C9	1.3872 (17)
C1—C2	1.4047 (17)	C8—H8	0.9300
C1—C7	1.4869 (16)	C9—N2	1.3554 (18)
C2—O3	1.3482 (16)	C9—C10	1.3966 (19)
C2—C3	1.3868 (18)	C10—C11	1.3669 (19)
C3—C4	1.3772 (19)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.3741 (19)
C4—O4	1.3577 (15)	C11—H11	0.9300
C4—C5	1.3965 (18)	C12—N1	1.3262 (18)
C5—C6	1.3699 (17)	C12—H12	0.9300
C5—H5A	0.9300	N1—H1	0.871 (9)
C6—H6	0.9300	N2—H2A	0.853 (9)
C7—O2	1.2551 (16)	N2—H2B	0.858 (9)
C7—O1	1.2699 (15)	O3—H3A	0.8200
C8—N1	1.3366 (17)	O4—H4	0.8200
C6—C1—C2	117.52 (11)	N1—C8—H8	119.9
C6—C1—C7	121.47 (11)	C9—C8—H8	119.9
C2—C1—C7	121.01 (11)	N2—C9—C8	121.43 (13)
O3—C2—C3	118.01 (12)	N2—C9—C10	121.62 (12)
O3—C2—C1	121.26 (12)	C8—C9—C10	116.95 (12)
C3—C2—C1	120.73 (12)	C11—C10—C9	120.89 (12)
C4—C3—C2	120.04 (12)	C11—C10—H10	119.6
C4—C3—H3	120.0	C9—C10—H10	119.6
C2—C3—H3	120.0	C10—C11—C12	119.69 (13)
O4—C4—C3	118.69 (11)	C10—C11—H11	120.2
O4—C4—C5	121.00 (12)	C12—C11—H11	120.2
C3—C4—C5	120.31 (11)	N1—C12—C11	118.93 (12)
C6—C5—C4	119.15 (12)	N1—C12—H12	120.5
C6—C5—H5A	120.4	C11—C12—H12	120.5
C4—C5—H5A	120.4	C12—N1—C8	123.39 (11)
C5—C6—C1	122.19 (11)	C12—N1—H1	122.3 (12)
C5—C6—H6	118.9	C8—N1—H1	114.3 (12)
C1—C6—H6	118.9	C9—N2—H2A	119.6 (11)
O2—C7—O1	122.24 (11)	C9—N2—H2B	117.2 (13)
O2—C7—C1	119.13 (11)	H2A—N2—H2B	122.9 (18)
O1—C7—C1	118.64 (11)	C2—O3—H3A	109.5
N1—C8—C9	120.14 (12)	C4—O4—H4	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1^i	0.82	1.85	2.6533 (14)	168
N1—H1···O1	0.87 (1)	1.80 (1)	2.6723 (13)	176 (2)
O3—H3A···O2	0.82	1.82	2.5520 (14)	148
N2—H2B···O4^ii	0.86 (1)	2.19 (1)	3.0339 (16)	169 (2)
N2—H2A···O2^iii	0.85 (1)	2.14 (1)	2.9497 (18)	157 (2)

Symmetry codes: (i) −x+3/2, y+1/2, −z+5/2; (ii) x, y−1, z−1; (iii) x−1/2, −y+3/2, z−1/2.