Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050787/bh2138sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050787/bh2138Isup2.hkl |
CCDC reference: 667395
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.
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 Uiso(H) = 1.2Ueq(carrier C).
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.
For related literature, see: Banerjee et al. (2006); Zeng et al. (2005).
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).
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) Å3 | 0.42 × 0.16 × 0.10 mm |
Z = 4 |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0512P)2 + 0.2552P] where P = (Fo2 + 2Fc2)/3 |
3261 reflections | (Δ/σ)max < 0.001 |
233 parameters | Δρmax = 0.15 e Å−3 |
4 restraints | Δρmin = −0.19 e Å−3 |
C5H7N2+·C14H11O3− | V = 1668.1 (7) Å3 |
Mr = 322.35 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.041 (2) Å | µ = 0.09 mm−1 |
b = 14.371 (3) Å | T = 298 K |
c = 11.953 (3) Å | 0.42 × 0.16 × 0.10 mm |
β = 104.714 (3)° |
Bruker SMART APEX CCD area-detector diffractometer | 3261 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 2373 reflections with I > 2σ(I) |
Tmin = 0.964, Tmax = 0.991 | Rint = 0.027 |
8927 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 4 restraints |
wR(F2) = 0.125 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.15 e Å−3 |
3261 reflections | Δρmin = −0.19 e Å−3 |
233 parameters |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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···O1i | 0.86 (1) | 2.02 (1) | 2.879 (2) | 179 (2) |
N2—H2B···O2ii | 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···O1i | 0.83 (1) | 2.02 (2) | 2.6917 (17) | 138 (2) |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C5H7N2+·C14H11O3− |
Mr | 322.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 10.041 (2), 14.371 (3), 11.953 (3) |
β (°) | 104.714 (3) |
V (Å3) | 1668.1 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.42 × 0.16 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.964, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8927, 3261, 2373 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.125, 1.06 |
No. of reflections | 3261 |
No. of parameters | 233 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.15, −0.19 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3 | 0.868 (9) | 1.870 (10) | 2.7264 (19) | 168.6 (19) |
N2—H2A···O1i | 0.860 (9) | 2.020 (10) | 2.879 (2) | 179.2 (18) |
N2—H2B···O2ii | 0.869 (9) | 1.965 (11) | 2.820 (2) | 167.4 (19) |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x+1, y, z. |
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.