The structure of the organic–inorganic hybrid material 4-aminopyridinium nitrate, C
5H
7N
2+·NO
3−, exhibits classical and bifurcated strong N—H
O hydrogen-bonding interactions, as well as weaker C—H
O interactions. Organic 4-aminopyridinium cations and inorganic nitrate anions interact to form a one-dimensional hydrogen-bonded ribbon in the
a direction. Neighbouring ribbons interact to form two-dimensional corrugated hydrogen-bonded sheets parallel to the
ac plane.
Supporting information
CCDC reference: 282223
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (Wave) = 0.000 Å
- R factor = 0.048
- wR factor = 0.116
- Data-to-parameter ratio = 20.6
checkCIF/PLATON results
No syntax errors found
Alert level A
DIFF019_ALERT_1_A _diffrn_standards_number is missing
Number of standards used in measurement.
DIFF020_ALERT_1_A _diffrn_standards_interval_count and
_diffrn_standards_interval_time are missing. Number of measurements
between standards or time (min) between standards.
2 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXL97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
4-Aminopyridinium nitrate
top
Crystal data top
C5H7N2+·NO3− | F(000) = 328 |
Mr = 157.14 | Dx = 1.496 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 209 reflections |
a = 9.192 (4) Å | θ = 2–30° |
b = 6.996 (4) Å | µ = 0.13 mm−1 |
c = 10.869 (5) Å | T = 200 K |
β = 93.60 (4)° | Needle, colourless |
V = 697.5 (6) Å3 | 0.20 × 0.20 × 0.20 mm |
Z = 4 | |
Data collection top
Oxford Excalibur2 diffractometer | 1369 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.036 |
Graphite monochromator | θmax = 31.8°, θmin = 4.2° |
ω/2θ scans | h = −13→13 |
6090 measured reflections | k = −10→8 |
2220 independent reflections | l = −16→15 |
Refinement top
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) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0545P)2] where P = (Fo2 + 2Fc2)/3 |
2220 reflections | (Δ/σ)max = 0.002 |
108 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
H1A | 0.5501 (19) | 0.193 (2) | 0.9511 (17) | 0.054 (5)* | |
H1B | 0.577 (2) | 0.104 (2) | 0.8252 (19) | 0.062 (6)* | |
O1 | 0.77850 (11) | 0.05911 (14) | 0.74230 (9) | 0.0353 (3) | |
N1 | 0.51723 (13) | 0.13733 (18) | 0.87877 (13) | 0.0331 (3) | |
C1 | 0.37418 (14) | 0.12040 (16) | 0.85447 (12) | 0.0247 (3) | |
O2 | 0.62171 (11) | 0.13015 (15) | 0.59360 (10) | 0.0449 (3) | |
N2 | 0.07612 (13) | 0.09205 (16) | 0.80423 (12) | 0.0326 (3) | |
H2A | −0.0165 | 0.0849 | 0.7879 | 0.039* | |
N3 | 0.75137 (12) | 0.11466 (15) | 0.63267 (11) | 0.0289 (3) | |
C5 | 0.27392 (14) | 0.17066 (19) | 0.94304 (12) | 0.0281 (3) | |
H5 | 0.3079 | 0.2132 | 1.0206 | 0.034* | |
C2 | 0.31506 (15) | 0.04882 (18) | 0.74069 (12) | 0.0292 (3) | |
H2 | 0.3767 | 0.0091 | 0.6810 | 0.035* | |
C4 | 0.12835 (15) | 0.15669 (18) | 0.91469 (13) | 0.0322 (3) | |
H4 | 0.0636 | 0.1926 | 0.9729 | 0.039* | |
O3 | 0.85311 (12) | 0.15115 (16) | 0.56697 (9) | 0.0431 (3) | |
C3 | 0.16864 (16) | 0.03793 (19) | 0.71823 (13) | 0.0321 (3) | |
H3 | 0.1308 | −0.0075 | 0.6424 | 0.039* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0318 (6) | 0.0452 (6) | 0.0290 (5) | 0.0023 (4) | 0.0024 (4) | 0.0032 (4) |
N1 | 0.0240 (6) | 0.0430 (7) | 0.0327 (7) | −0.0007 (5) | 0.0042 (5) | 0.0001 (6) |
C1 | 0.0255 (7) | 0.0217 (6) | 0.0271 (7) | 0.0022 (5) | 0.0029 (5) | 0.0042 (5) |
O2 | 0.0286 (6) | 0.0582 (7) | 0.0467 (7) | −0.0011 (5) | −0.0063 (5) | 0.0069 (5) |
N2 | 0.0233 (6) | 0.0341 (6) | 0.0399 (7) | −0.0003 (4) | −0.0022 (5) | 0.0041 (5) |
N3 | 0.0268 (6) | 0.0288 (6) | 0.0310 (6) | −0.0025 (4) | 0.0026 (5) | −0.0031 (5) |
C5 | 0.0285 (7) | 0.0301 (7) | 0.0259 (7) | 0.0019 (5) | 0.0023 (5) | −0.0016 (5) |
C2 | 0.0347 (8) | 0.0265 (7) | 0.0267 (7) | 0.0032 (5) | 0.0058 (6) | −0.0007 (5) |
C4 | 0.0316 (8) | 0.0315 (7) | 0.0342 (8) | 0.0063 (6) | 0.0087 (6) | 0.0028 (6) |
O3 | 0.0382 (6) | 0.0555 (7) | 0.0369 (6) | −0.0103 (5) | 0.0137 (5) | −0.0002 (5) |
C3 | 0.0376 (8) | 0.0300 (7) | 0.0282 (7) | −0.0012 (6) | −0.0029 (6) | −0.0012 (6) |
Geometric parameters (Å, º) top
O1—N3 | 1.2632 (15) | N2—H2A | 0.8600 |
N1—C1 | 1.3301 (18) | N3—O3 | 1.2383 (15) |
N1—H1A | 0.913 (19) | C5—C4 | 1.3577 (19) |
N1—H1B | 0.86 (2) | C5—H5 | 0.9300 |
C1—C2 | 1.4110 (19) | C2—C3 | 1.355 (2) |
C1—C5 | 1.4181 (18) | C2—H2 | 0.9300 |
O2—N3 | 1.2446 (15) | C4—H4 | 0.9300 |
N2—C4 | 1.3431 (18) | C3—H3 | 0.9300 |
N2—C3 | 1.3564 (19) | | |
| | | |
C1—N1—H1A | 118.6 (11) | C4—C5—C1 | 120.09 (13) |
C1—N1—H1B | 120.6 (14) | C4—C5—H5 | 120.0 |
H1A—N1—H1B | 120.6 (18) | C1—C5—H5 | 120.0 |
N1—C1—C2 | 121.81 (13) | C3—C2—C1 | 120.10 (13) |
N1—C1—C5 | 121.31 (13) | C3—C2—H2 | 120.0 |
C2—C1—C5 | 116.87 (12) | C1—C2—H2 | 120.0 |
C4—N2—C3 | 120.37 (12) | N2—C4—C5 | 121.27 (13) |
C4—N2—H2A | 119.8 | N2—C4—H4 | 119.4 |
C3—N2—H2A | 119.8 | C5—C4—H4 | 119.4 |
O3—N3—O2 | 121.80 (13) | C2—C3—N2 | 121.25 (13) |
O3—N3—O1 | 119.72 (12) | C2—C3—H3 | 119.4 |
O2—N3—O1 | 118.48 (12) | N2—C3—H3 | 119.4 |
| | | |
N1—C1—C5—C4 | 178.28 (13) | C3—N2—C4—C5 | 0.37 (19) |
C2—C1—C5—C4 | −2.77 (18) | C1—C5—C4—N2 | 1.3 (2) |
N1—C1—C2—C3 | −178.43 (13) | C1—C2—C3—N2 | −1.1 (2) |
C5—C1—C2—C3 | 2.63 (18) | C4—N2—C3—C2 | −0.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O2 | 0.86 (2) | 2.58 (2) | 3.302 (2) | 142.5 (17) |
N1—H1B···O1 | 0.86 (2) | 2.14 (2) | 2.952 (2) | 159.3 (19) |
N2—H2A···O1i | 0.88 (2) | 1.90 (2) | 2.784 (2) | 175 (2) |
N2—H2A···O3i | 0.88 (2) | 2.66 (2) | 3.218 (2) | 122 (2) |
N2—H2A···N3i | 0.88 (2) | 2.63 (2) | 3.421 (2) | 149 (2) |
Symmetry code: (i) x−1, y, z. |