2-Amino­pyridinium 5-formyl­salicylate

In the crystal structure of the title compound, (2APH)⁺(5FSAH)^- (2AP is 2-amino­pyridine and 5FSAH₂ is 5-formyl­salicylic acid) or C₅H₇N₂⁺·C₈H₅O₄^-, (2APH)⁺ cations and (5FSAH)^- anions are connected through hydrogen bonds, forming a one-dimenstional chain structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.069
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         49 Perc.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C7      ..       5.76 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   C7      ..       5.08 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C5      ..       6.62 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C8      ..       5.37 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5     -   C6      ..       5.63 su

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

2-Aminopyridinium 5-formylsalicylate

Crystal data

C5H7N2^+·C8H5O4^−	F(000) = 544
Mr = 260.25	Dx = 1.434 Mg m^−3
Monoclinic, P21/c	Melting point: not measured K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71069 Å
a = 12.358 (5) Å	Cell parameters from 7362 reflections
b = 7.191 (5) Å	θ = 1.7–28.3°
c = 14.000 (5) Å	µ = 0.11 mm^−1
β = 104.382 (5)°	T = 293 K
V = 1205.1 (11) Å^3	Block, colorless
Z = 4	0.43 × 0.25 × 0.23 mm

Data collection

Bruker APEX CCD area-detector diffractometer	2842 independent reflections
Radiation source: fine-focus sealed tube	1387 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→14
Tmin = 0.866, Tmax = 0.976	k = −9→9
7481 measured reflections	l = −16→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0181P)^2] where P = (Fo^2 + 2Fc^2)/3
2842 reflections	(Δ/σ)max < 0.001
198 parameters	Δρmax = 0.15 e Å^−3
4 restraints	Δρmin = −0.19 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O3	0.42003 (8)	1.15821 (15)	0.37925 (7)	0.0547 (3)
O2	0.34922 (8)	1.18940 (14)	0.50969 (7)	0.0514 (3)
O1	0.16027 (10)	1.06425 (17)	0.50796 (7)	0.0603 (3)
N1	0.45351 (10)	0.67696 (18)	0.38316 (9)	0.0437 (3)
C1	0.14860 (12)	1.0206 (2)	0.41238 (10)	0.0402 (4)
N2	0.37381 (13)	0.6796 (2)	0.51415 (10)	0.0540 (4)
C6	0.23307 (11)	1.06116 (19)	0.36477 (9)	0.0344 (4)
C10	0.36544 (12)	0.64159 (19)	0.41971 (10)	0.0386 (4)
C11	0.26838 (12)	0.56766 (19)	0.35588 (10)	0.0439 (4)
H11	0.2052	0.5434	0.3786	0.053*
O4	0.15749 (10)	0.92914 (17)	0.05723 (8)	0.0728 (4)
C4	0.11392 (12)	0.9412 (2)	0.21273 (10)	0.0375 (4)
C5	0.21343 (12)	1.0209 (2)	0.26531 (10)	0.0389 (4)
H5	0.2685	1.0479	0.2326	0.039 (4)
C2	0.05010 (12)	0.9349 (2)	0.36195 (10)	0.0456 (4)
H2	−0.0043	0.9036	0.3947	0.055*
C7	0.34315 (12)	1.1421 (2)	0.42032 (11)	0.0408 (4)
C9	0.45406 (13)	0.6411 (2)	0.28852 (11)	0.0516 (4)
H14	0.5175	0.6666	0.2664	0.062*
C3	0.03397 (12)	0.8971 (2)	0.26326 (10)	0.0437 (4)
H3	−0.0322	0.8406	0.2295	0.052*
C12	0.26875 (13)	0.5327 (2)	0.26099 (10)	0.0495 (4)
H12	0.2051	0.4838	0.2184	0.059*
C8	0.09260 (16)	0.9002 (2)	0.10796 (12)	0.0521 (5)
C13	0.36264 (14)	0.5684 (2)	0.22592 (11)	0.0515 (4)
H13	0.3625	0.5428	0.1608	0.062*
H4	0.0160 (12)	0.8491 (18)	0.0747 (9)	0.057 (5)*
H8	0.5186 (9)	0.7248 (19)	0.4219 (9)	0.072 (6)*
H7	0.4383 (10)	0.733 (2)	0.5501 (10)	0.086 (6)*
H6	0.3157 (11)	0.644 (2)	0.5371 (12)	0.088 (7)*
H1	0.2282 (10)	1.122 (2)	0.5254 (12)	0.104 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0366 (7)	0.0797 (9)	0.0498 (7)	−0.0101 (6)	0.0143 (5)	−0.0060 (6)
O2	0.0453 (7)	0.0716 (8)	0.0356 (6)	−0.0107 (6)	0.0068 (5)	−0.0064 (6)
O1	0.0499 (8)	0.0971 (10)	0.0356 (6)	−0.0128 (7)	0.0139 (5)	−0.0055 (6)
N1	0.0354 (9)	0.0540 (9)	0.0405 (8)	−0.0040 (7)	0.0069 (7)	−0.0022 (7)
C1	0.0375 (10)	0.0515 (11)	0.0314 (9)	0.0016 (8)	0.0080 (7)	0.0026 (8)
N2	0.0482 (10)	0.0726 (11)	0.0426 (9)	−0.0094 (9)	0.0135 (8)	−0.0088 (8)
C6	0.0315 (9)	0.0384 (9)	0.0329 (8)	0.0026 (7)	0.0069 (7)	0.0035 (7)
C10	0.0416 (10)	0.0385 (10)	0.0349 (9)	0.0037 (8)	0.0079 (7)	0.0006 (7)
C11	0.0366 (10)	0.0471 (11)	0.0459 (10)	−0.0043 (8)	0.0064 (8)	0.0005 (8)
O4	0.0658 (9)	0.1099 (11)	0.0466 (7)	−0.0013 (7)	0.0213 (6)	−0.0059 (7)
C4	0.0327 (9)	0.0440 (10)	0.0346 (8)	0.0024 (8)	0.0059 (7)	−0.0003 (8)
C5	0.0355 (10)	0.0434 (11)	0.0407 (10)	0.0044 (8)	0.0147 (8)	0.0050 (8)
H5	0.037 (10)	0.046 (10)	0.032 (9)	0.006 (8)	0.002 (7)	−0.019 (7)
C2	0.0331 (10)	0.0616 (11)	0.0440 (9)	−0.0035 (8)	0.0132 (7)	0.0043 (9)
C7	0.0384 (10)	0.0422 (10)	0.0404 (10)	0.0027 (8)	0.0071 (8)	0.0049 (8)
C9	0.0534 (11)	0.0613 (12)	0.0431 (10)	−0.0046 (9)	0.0177 (8)	−0.0010 (9)
C3	0.0317 (9)	0.0496 (11)	0.0472 (10)	−0.0012 (7)	0.0045 (7)	−0.0002 (8)
C12	0.0461 (11)	0.0528 (11)	0.0431 (10)	−0.0051 (9)	−0.0010 (8)	−0.0007 (8)
C8	0.0467 (12)	0.0651 (13)	0.0433 (10)	0.0008 (9)	0.0090 (9)	−0.0030 (9)
C13	0.0568 (12)	0.0606 (12)	0.0363 (9)	−0.0068 (9)	0.0101 (9)	−0.0025 (9)

Geometric parameters (Å, º)

O3—C7	1.2322 (16)	C11—H11	0.9300
O2—C7	1.2808 (16)	O4—C8	1.2140 (18)
O1—C1	1.3467 (16)	C4—C5	1.3903 (19)
O1—H1	0.912 (9)	C4—C3	1.3872 (19)
N1—C10	1.3370 (18)	C4—C8	1.454 (2)
N1—C9	1.3514 (18)	C5—H5	0.9300
N1—H8	0.918 (9)	C2—C3	1.3733 (18)
C1—C2	1.3904 (19)	C2—H2	0.9300
C1—C6	1.402 (2)	C9—C13	1.351 (2)
N2—C10	1.3288 (19)	C9—H14	0.9300
N2—H7	0.916 (9)	C3—H3	0.9300
N2—H6	0.894 (9)	C12—C13	1.392 (2)
C6—C5	1.3834 (18)	C12—H12	0.9300
C6—C7	1.506 (2)	C8—H4	1.015 (13)
C10—C11	1.4098 (19)	C13—H13	0.9300
C11—C12	1.3532 (18)
C1—O1—H1	103.6 (11)	C6—C5—H5	119.0
C10—N1—C9	122.80 (14)	C4—C5—H5	119.0
C10—N1—H8	121.5 (9)	C3—C2—C1	119.25 (14)
C9—N1—H8	115.7 (9)	C3—C2—H2	120.4
O1—C1—C2	118.16 (14)	C1—C2—H2	120.4
O1—C1—C6	121.03 (13)	O3—C7—O2	124.47 (14)
C2—C1—C6	120.81 (13)	O3—C7—C6	119.84 (14)
C10—N2—H7	118.4 (10)	O2—C7—C6	115.68 (13)
C10—N2—H6	115.3 (11)	N1—C9—C13	120.18 (16)
H7—N2—H6	126.3 (15)	N1—C9—H14	119.9
C5—C6—C1	118.03 (13)	C13—C9—H14	119.9
C5—C6—C7	120.72 (13)	C2—C3—C4	121.61 (14)
C1—C6—C7	121.23 (13)	C2—C3—H3	119.2
N2—C10—N1	118.17 (15)	C4—C3—H3	119.2
N2—C10—C11	123.49 (15)	C11—C12—C13	121.23 (14)
N1—C10—C11	118.33 (14)	C11—C12—H12	119.4
C12—C11—C10	118.85 (15)	C13—C12—H12	119.4
C12—C11—H11	120.6	O4—C8—C4	125.08 (17)
C10—C11—H11	120.6	O4—C8—H4	118.0 (8)
C5—C4—C3	118.19 (13)	C4—C8—H4	116.8 (8)
C5—C4—C8	122.16 (14)	C9—C13—C12	118.60 (15)
C3—C4—C8	119.64 (15)	C9—C13—H13	120.7
C6—C5—C4	122.03 (14)	C12—C13—H13	120.7
O1—C1—C6—C5	−176.90 (13)	C5—C6—C7—O3	−6.2 (2)
C2—C1—C6—C5	2.8 (2)	C1—C6—C7—O3	172.41 (14)
O1—C1—C6—C7	4.5 (2)	C5—C6—C7—O2	174.07 (13)
C2—C1—C6—C7	−175.81 (13)	C1—C6—C7—O2	−7.4 (2)
C9—N1—C10—N2	179.10 (14)	C10—N1—C9—C13	0.8 (2)
C9—N1—C10—C11	−1.5 (2)	C1—C2—C3—C4	0.4 (2)
N2—C10—C11—C12	−179.53 (14)	C5—C4—C3—C2	1.8 (2)
N1—C10—C11—C12	1.1 (2)	C8—C4—C3—C2	−179.36 (14)
C1—C6—C5—C4	−0.5 (2)	C10—C11—C12—C13	0.0 (2)
C7—C6—C5—C4	178.10 (14)	C5—C4—C8—O4	0.5 (3)
C3—C4—C5—C6	−1.7 (2)	C3—C4—C8—O4	−178.35 (16)
C8—C4—C5—C6	179.43 (14)	N1—C9—C13—C12	0.3 (2)
O1—C1—C2—C3	176.92 (13)	C11—C12—C13—C9	−0.7 (2)
C6—C1—C2—C3	−2.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H8···O2^i	0.92 (1)	1.79 (1)	2.7019 (18)	175 (1)
N2—H7···O3^i	0.92 (1)	1.95 (1)	2.862 (2)	177 (2)
O1—H1···O2	0.91 (1)	1.64 (1)	2.4970 (18)	155 (2)
N2—H6···O4^ii	0.89 (1)	2.11 (1)	2.987 (2)	167 (2)

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