2-Amino­pyridinium 2-hydr­oxy-2,2-di­phenyl­acetate

In the title salt, C₅H₇N₂⁺·C₁₄H₁₁O₃⁻, the cation and anion inter­act through N—H...O hydrogen bonds involving the protonated NH group of the cation and the hydroxyl group of the anion. Both H atoms of the NH₂ group in the cation are engaged in N—H...O hydrogen bonds with the carbonyl groups of two symmetry-related anions, forming an infinite one-dimensional chain in the [100] direction.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.125
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

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Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.52 Ratio

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

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

   3 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Rational design and synthesis of supramolecular architectures using hydrogen bonding interactions is still a hot field due to intriguing topologies and potential applications in opto-electronics and catalysis (Banerjee et al., 2006). A number of reports have been published in past decades (Zeng et al., 2005). Herein we present the structure of a supramolecular salt, 2-aminopyridinium 2-hydroxy-2,2-diphenylacetate, (I).

The asymmetric unit of the title salt consists of one 2-aminopyridinium cation and one 2-hydroxy-2,2-diphenylacetate anion, in which ions are connected through a N—H···O hydrogen bond (Table 1, entry 1). Within the anion, a weak contact between H3A and O1 is observed, generating a S(5) ring (Fig. 1 and Table 1). Finally, both amine H atoms in the cation link symmetry related anions through N—H···O(carbonyl) hydrogen bonds, giving an infinite one-dimensional chain along the direction [100], as shown in Fig. 2.

Related literature

For related literature, see: Banerjee et al. (2006); Zeng et al. (2005).

S2. Experimental

All reagents were commercially available and of analytical grade. A 5 ml e thanol solution of 2-aminopyridine (1.0 mmol, 0.094 g) was added to a 20 ml hot aqueous solution of 2-hydroxy-2,2-diphenylacetic acid (1.0 mmol, 0.23 g), and the mixture was stirred for 10 min. at 373 K. Then the solution was filtered, and the filtrate was kept at room temperature. After one week, colourless crystals of (I) were obtained.

S3. Refinement

H atoms bonded to N and O atoms were located in a difference map and refined isotropically with restrained bond lengths: N—H = 0.85 (1) Å and O—H = 0.82 (1). Other H atoms were placed in calculated positions and were refined as riding atoms with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(carrier C).

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Spek, 2003).

Figures

	Fig. 1. The asymmetric unit of (I). Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. An infinite one-dimensional chain along the [100] axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonds have been omitted for clarity.

2-Aminopyridinium 2-hydroxy-2,2-diphenylacetate

Crystal data

C5H7N2^+·C14H11O3^−	F(000) = 680
Mr = 322.35	Dx = 1.284 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5480 reflections
a = 10.041 (2) Å	θ = 2.5–28.3°
b = 14.371 (3) Å	µ = 0.09 mm^−1
c = 11.953 (3) Å	T = 298 K
β = 104.714 (3)°	Needle, colourless
V = 1668.1 (7) Å^3	0.42 × 0.16 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3261 independent reflections
Radiation source: fine-focus sealed tube	2373 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −12→12
Tmin = 0.964, Tmax = 0.991	k = −17→14
8927 measured reflections	l = −10→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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0512P)^2 + 0.2552P] where P = (Fo^2 + 2Fc^2)/3
3261 reflections	(Δ/σ)max < 0.001
233 parameters	Δρmax = 0.15 e Å^−3
4 restraints	Δρmin = −0.19 e Å^−3

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

	x	y	z	Uiso*/Ueq
N1	0.66548 (15)	0.18811 (10)	0.79894 (13)	0.0464 (4)
H1A	0.6111 (17)	0.1582 (13)	0.8324 (15)	0.066 (6)*
N2	0.85192 (18)	0.10260 (11)	0.90008 (14)	0.0510 (4)
H2A	0.7976 (16)	0.0720 (11)	0.9318 (14)	0.051 (5)*
H2B	0.9385 (11)	0.0888 (14)	0.9113 (17)	0.064 (6)*
O1	0.32779 (13)	0.00093 (8)	0.99259 (10)	0.0499 (3)
O2	0.12570 (12)	0.05947 (9)	0.89953 (11)	0.0554 (4)
O3	0.46608 (12)	0.10383 (8)	0.88096 (10)	0.0462 (3)
H3A	0.492 (2)	0.0586 (10)	0.9239 (15)	0.068 (7)*
C1	0.80094 (18)	0.16810 (11)	0.82341 (14)	0.0392 (4)
C2	0.88145 (19)	0.21943 (12)	0.76463 (15)	0.0480 (5)
H2	0.9756	0.2084	0.7793	0.058*
C3	0.8215 (2)	0.28468 (13)	0.68688 (17)	0.0579 (5)
H3	0.8753	0.3185	0.6485	0.069*
C4	0.6804 (2)	0.30249 (14)	0.66276 (17)	0.0601 (5)
H4	0.6396	0.3470	0.6083	0.072*
C5	0.6054 (2)	0.25355 (14)	0.72046 (18)	0.0575 (5)
H5	0.5114	0.2646	0.7065	0.069*
C6	0.25153 (17)	0.04849 (11)	0.91492 (14)	0.0372 (4)
C7	0.32230 (16)	0.09481 (11)	0.82693 (13)	0.0373 (4)
C8	0.27078 (17)	0.19414 (12)	0.79965 (14)	0.0396 (4)
C9	0.2831 (2)	0.25527 (12)	0.89119 (17)	0.0564 (5)
H9	0.3197	0.2342	0.9663	0.068*
C10	0.2424 (3)	0.34656 (14)	0.8732 (2)	0.0756 (7)
H10	0.2500	0.3862	0.9359	0.091*
C11	0.1907 (3)	0.37923 (15)	0.7633 (2)	0.0764 (7)
H11	0.1640	0.4412	0.7513	0.092*
C12	0.1784 (2)	0.32063 (16)	0.6711 (2)	0.0680 (6)
H12	0.1439	0.3428	0.5962	0.082*
C13	0.21746 (19)	0.22771 (13)	0.68924 (16)	0.0524 (5)
H13	0.2075	0.1879	0.6263	0.063*
C14	0.3004 (2)	0.03108 (12)	0.72152 (15)	0.0461 (4)
C15	0.1700 (2)	0.00022 (15)	0.66520 (17)	0.0635 (6)
H15	0.0941	0.0203	0.6898	0.076*
C16	0.1519 (3)	−0.06039 (17)	0.5723 (2)	0.0840 (8)
H16	0.0640	−0.0810	0.5352	0.101*
C17	0.2633 (4)	−0.09008 (17)	0.5349 (2)	0.0937 (9)
H17	0.2508	−0.1307	0.4725	0.112*
C18	0.3916 (4)	−0.06006 (18)	0.5889 (2)	0.0891 (8)
H18	0.4670	−0.0799	0.5633	0.107*
C19	0.4104 (2)	−0.00005 (14)	0.68190 (18)	0.0640 (6)
H19	0.4989	0.0198	0.7186	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0403 (9)	0.0447 (9)	0.0575 (9)	−0.0038 (7)	0.0186 (7)	0.0045 (7)
N2	0.0472 (10)	0.0529 (10)	0.0582 (10)	0.0026 (8)	0.0231 (8)	0.0141 (8)
O1	0.0464 (7)	0.0562 (8)	0.0500 (7)	0.0097 (6)	0.0174 (6)	0.0208 (6)
O2	0.0392 (7)	0.0659 (9)	0.0660 (9)	0.0063 (6)	0.0220 (6)	0.0166 (7)
O3	0.0346 (7)	0.0519 (8)	0.0523 (7)	0.0023 (6)	0.0114 (6)	0.0184 (6)
C1	0.0411 (10)	0.0374 (9)	0.0413 (9)	−0.0027 (7)	0.0147 (7)	−0.0022 (7)
C2	0.0435 (10)	0.0498 (11)	0.0547 (11)	−0.0058 (8)	0.0195 (9)	0.0039 (9)
C3	0.0660 (14)	0.0535 (12)	0.0581 (12)	−0.0147 (10)	0.0231 (10)	0.0083 (9)
C4	0.0677 (14)	0.0478 (11)	0.0602 (12)	0.0020 (10)	0.0079 (10)	0.0127 (9)
C5	0.0464 (11)	0.0539 (12)	0.0691 (13)	0.0055 (9)	0.0090 (10)	0.0061 (10)
C6	0.0391 (10)	0.0347 (9)	0.0401 (9)	0.0024 (7)	0.0142 (7)	0.0020 (7)
C7	0.0339 (9)	0.0420 (9)	0.0370 (9)	0.0039 (7)	0.0110 (7)	0.0070 (7)
C8	0.0367 (9)	0.0406 (9)	0.0447 (9)	0.0010 (7)	0.0160 (7)	0.0099 (7)
C9	0.0735 (14)	0.0438 (11)	0.0524 (11)	−0.0004 (10)	0.0169 (10)	0.0030 (9)
C10	0.1036 (19)	0.0426 (12)	0.0858 (17)	0.0020 (12)	0.0335 (14)	0.0005 (11)
C11	0.0910 (18)	0.0438 (12)	0.1058 (19)	0.0132 (11)	0.0459 (15)	0.0213 (13)
C12	0.0679 (14)	0.0692 (14)	0.0724 (14)	0.0177 (11)	0.0277 (11)	0.0388 (12)
C13	0.0541 (11)	0.0582 (12)	0.0489 (10)	0.0105 (9)	0.0202 (9)	0.0150 (9)
C14	0.0574 (12)	0.0404 (9)	0.0428 (10)	0.0053 (8)	0.0169 (9)	0.0069 (8)
C15	0.0679 (14)	0.0661 (13)	0.0516 (12)	0.0014 (11)	0.0064 (10)	−0.0016 (10)
C16	0.107 (2)	0.0689 (15)	0.0620 (14)	−0.0041 (14)	−0.0038 (14)	−0.0077 (12)
C17	0.163 (3)	0.0606 (15)	0.0581 (15)	0.0115 (18)	0.0289 (18)	−0.0135 (12)
C18	0.130 (3)	0.0702 (16)	0.0835 (18)	0.0126 (16)	0.0579 (18)	−0.0136 (14)
C19	0.0782 (15)	0.0563 (12)	0.0699 (13)	0.0022 (11)	0.0413 (12)	−0.0052 (10)

Geometric parameters (Å, º)

N1—C1	1.348 (2)	C8—C9	1.384 (2)
N1—C5	1.357 (2)	C9—C10	1.375 (3)
N1—H1A	0.868 (9)	C9—H9	0.9300
N2—C1	1.323 (2)	C10—C11	1.366 (3)
N2—H2A	0.860 (9)	C10—H10	0.9300
N2—H2B	0.869 (9)	C11—C12	1.367 (3)
O1—C6	1.2467 (18)	C11—H11	0.9300
O2—C6	1.240 (2)	C12—C13	1.393 (3)
O3—C7	1.430 (2)	C12—H12	0.9300
O3—H3A	0.829 (9)	C13—H13	0.9300
C1—C2	1.407 (2)	C14—C19	1.382 (3)
C2—C3	1.350 (3)	C14—C15	1.384 (3)
C2—H2	0.9300	C15—C16	1.386 (3)
C3—C4	1.395 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.374 (4)
C4—C5	1.342 (3)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.357 (4)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.560 (2)	C18—C19	1.381 (3)
C7—C8	1.525 (2)	C18—H18	0.9300
C7—C14	1.528 (2)	C19—H19	0.9300
C8—C13	1.379 (2)
C1—N1—C5	123.01 (16)	C10—C9—C8	121.23 (19)
C1—N1—H1A	120.9 (14)	C10—C9—H9	119.4
C5—N1—H1A	116.1 (14)	C8—C9—H9	119.4
C1—N2—H2A	119.5 (12)	C11—C10—C9	120.2 (2)
C1—N2—H2B	117.8 (14)	C11—C10—H10	119.9
H2A—N2—H2B	122.5 (19)	C9—C10—H10	119.9
C7—O3—H3A	109.6 (15)	C10—C11—C12	119.8 (2)
N2—C1—N1	119.59 (16)	C10—C11—H11	120.1
N2—C1—C2	123.28 (17)	C12—C11—H11	120.1
N1—C1—C2	117.12 (16)	C11—C12—C13	120.0 (2)
C3—C2—C1	119.71 (17)	C11—C12—H12	120.0
C3—C2—H2	120.1	C13—C12—H12	120.0
C1—C2—H2	120.1	C8—C13—C12	120.6 (2)
C2—C3—C4	121.45 (18)	C8—C13—H13	119.7
C2—C3—H3	119.3	C12—C13—H13	119.7
C4—C3—H3	119.3	C19—C14—C15	117.98 (19)
C5—C4—C3	118.05 (18)	C19—C14—C7	121.10 (17)
C5—C4—H4	121.0	C15—C14—C7	120.89 (17)
C3—C4—H4	121.0	C14—C15—C16	120.4 (2)
C4—C5—N1	120.64 (19)	C14—C15—H15	119.8
C4—C5—H5	119.7	C16—C15—H15	119.8
N1—C5—H5	119.7	C17—C16—C15	120.2 (3)
O2—C6—O1	126.18 (16)	C17—C16—H16	119.9
O2—C6—C7	117.85 (14)	C15—C16—H16	119.9
O1—C6—C7	115.92 (14)	C18—C17—C16	120.0 (2)
O3—C7—C8	105.10 (13)	C18—C17—H17	120.0
O3—C7—C14	110.13 (13)	C16—C17—H17	120.0
C8—C7—C14	114.51 (13)	C17—C18—C19	120.0 (3)
O3—C7—C6	108.35 (12)	C17—C18—H18	120.0
C8—C7—C6	110.83 (13)	C19—C18—H18	120.0
C14—C7—C6	107.78 (13)	C18—C19—C14	121.4 (2)
C13—C8—C9	118.00 (17)	C18—C19—H19	119.3
C13—C8—C7	124.07 (16)	C14—C19—H19	119.3
C9—C8—C7	117.89 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.87 (1)	1.87 (1)	2.7264 (19)	169 (2)
N2—H2A···O1^i	0.86 (1)	2.02 (1)	2.879 (2)	179 (2)
N2—H2B···O2^ii	0.87 (1)	1.97 (1)	2.820 (2)	167 (2)
O3—H3A···O1	0.83 (1)	2.19 (2)	2.6147 (17)	112 (2)
O3—H3A···O1^i	0.83 (1)	2.02 (2)	2.6917 (17)	138 (2)

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