The crystal structure of the title compound, C7H8NO2+·NO3-, consists of anionic and cationic layers linked by a complex three-dimensional hydrogen-bond network. Each cationic layer contains organic groups (NH3C6H4COOH)+, and each anionic layer contains inorganic (NO3)-. The structure is stabilized by two types of hydrogen-bonding interaction: anion-cation and cation-cation contacts.
Supporting information
CCDC reference: 180791
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.057
- Data-to-parameter ratio = 10.4
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: CAD-4 Operations Manual (Enraf-Nonius, 1989); cell refinement: CAD-4 Operations Manual; data reduction: BEGIN_SDP (Frenz et al., 1985); program(s) used to solve structure: MULTAN (Main et al., 1980); program(s) used to refine structure: CAD-4 Operations Manual [Is this correct?]; molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CIF VAX in MolEN (Fair, 1990).
m-carboxy phenyl ammonium nitrate
top
Crystal data top
C7H8NO2+·NO3− | F(000) = 832 |
Mr = 200.15 | Dx = 1.517 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 31.838 (2) Å | θ = 10–14° |
b = 5.208 (1) Å | µ = 0.13 mm−1 |
c = 11.117 (3) Å | T = 298 K |
β = 108.06 (4)° | Prism, brown |
V = 1752.4 (7) Å3 | 0.60 × 0.40 × 0.30 mm |
Z = 8 | |
Data collection top
MACH3 diffractometer | θmax = 30.0° |
Radiation source: X-ray_tube | h = 0→44 |
θ/2θ scans | k = 0→7 |
2923 measured reflections | l = −15→14 |
2551 independent reflections | 2 standard reflections every 60 reflections |
1654 reflections with I > 3σ(I) | intensity decay: −4.2% |
Rint = 0.018 | |
Refinement top
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.057 | All H-atom parameters refined |
S = 1.13 | w = 4Fo2/[σ2(Fo2) + 0.0016Fo4] |
1654 reflections | (Δ/σ)max = 0.006 |
159 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.07 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.30481 (3) | −0.1207 (2) | 0.0894 (1) | 0.0461 (3) | |
O2 | 0.25276 (3) | −0.0041 (2) | −0.0883 (1) | 0.0414 (3) | |
O3 | 0.45029 (4) | 0.8578 (2) | 0.1933 (1) | 0.0479 (3) | |
O4 | 0.46750 (4) | 0.6164 (2) | 0.3578 (1) | 0.0480 (3) | |
O5 | 0.45388 (6) | 1.0155 (3) | 0.3752 (1) | 0.0814 (5) | |
N1 | 0.44230 (4) | 0.3585 (3) | 0.0853 (1) | 0.0360 (3) | |
N2 | 0.45727 (4) | 0.8322 (2) | 0.3106 (1) | 0.0381 (3) | |
C1 | 0.28983 (4) | 0.0198 (3) | −0.0125 (1) | 0.0317 (3) | |
C2 | 0.32174 (4) | 0.2117 (3) | −0.0317 (1) | 0.0296 (3) | |
C3 | 0.36613 (4) | 0.2023 (3) | 0.0409 (1) | 0.0298 (3) | |
C4 | 0.39523 (4) | 0.3744 (3) | 0.0143 (1) | 0.0299 (3) | |
C5 | 0.38102 (5) | 0.5582 (3) | −0.0791 (1) | 0.0378 (4) | |
C6 | 0.33674 (5) | 0.5676 (3) | −0.1497 (1) | 0.0408 (4) | |
C7 | 0.30705 (4) | 0.3937 (3) | −0.1268 (1) | 0.0357 (3) | |
H | 0.2852 (6) | −0.244 (4) | 0.091 (2) | 0.053 (5)* | |
H1n | 0.4564 (5) | 0.347 (4) | 0.027 (2) | 0.047 (5)* | |
H2n | 0.4483 (6) | 0.217 (4) | 0.137 (2) | 0.053 (5)* | |
H3n | 0.4502 (7) | 0.498 (4) | 0.137 (2) | 0.074 (7)* | |
H3 | 0.3770 (5) | 0.073 (3) | 0.106 (2) | 0.044 (5)* | |
H5 | 0.4014 (6) | 0.677 (4) | −0.096 (2) | 0.046 (5)* | |
H6 | 0.3260 (6) | 0.701 (4) | −0.212 (2) | 0.052 (5)* | |
H7 | 0.2761 (5) | 0.392 (4) | −0.179 (2) | 0.044 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0371 (5) | 0.0499 (6) | 0.0455 (5) | −0.0145 (5) | 0.0044 (4) | 0.0171 (4) |
O2 | 0.0292 (4) | 0.0449 (6) | 0.0444 (5) | −0.0033 (5) | 0.0030 (4) | 0.0120 (4) |
O3 | 0.0444 (5) | 0.0485 (6) | 0.0463 (5) | −0.0085 (5) | 0.0074 (4) | −0.0046 (5) |
O4 | 0.0526 (5) | 0.0356 (5) | 0.0641 (6) | −0.0132 (5) | 0.0303 (4) | −0.0094 (5) |
O5 | 0.123 (1) | 0.0476 (7) | 0.0838 (8) | 0.0141 (6) | 0.0472 (6) | −0.0230 (7) |
N1 | 0.0261 (4) | 0.0385 (6) | 0.0435 (5) | 0.0055 (5) | 0.0109 (4) | 0.0097 (4) |
N2 | 0.0334 (5) | 0.0315 (6) | 0.0523 (6) | −0.0003 (5) | 0.0176 (4) | −0.0063 (5) |
C1 | 0.0291 (5) | 0.0331 (7) | 0.0323 (5) | 0.0006 (5) | 0.0086 (4) | 0.0061 (5) |
C2 | 0.0274 (5) | 0.0286 (6) | 0.0329 (5) | 0.0005 (5) | 0.0097 (4) | 0.0050 (5) |
C3 | 0.0271 (5) | 0.0279 (6) | 0.0339 (6) | −0.0010 (5) | 0.0085 (4) | 0.0039 (5) |
C4 | 0.0267 (5) | 0.0288 (6) | 0.0349 (6) | 0.0038 (5) | 0.0106 (4) | 0.0047 (5) |
C5 | 0.0385 (6) | 0.0325 (7) | 0.0459 (6) | −0.0032 (6) | 0.0184 (5) | 0.0074 (5) |
C6 | 0.0446 (7) | 0.0359 (7) | 0.0421 (6) | −0.0109 (6) | 0.0138 (5) | 0.0002 (6) |
C7 | 0.0328 (6) | 0.0392 (7) | 0.0334 (6) | −0.0035 (6) | 0.0077 (5) | 0.0009 (6) |
Geometric parameters (Å, º) top
O1—C1 | 1.308 (2) | C2—C3 | 1.394 (2) |
O1—H | 0.90 (2) | C2—C7 | 1.389 (2) |
O2—C1 | 1.225 (1) | C3—C4 | 1.385 (2) |
O3—N2 | 1.260 (2) | C3—H3 | 0.98 (2) |
O4—N2 | 1.240 (2) | C4—C5 | 1.381 (2) |
O5—N2 | 1.219 (2) | C5—C6 | 1.385 (2) |
N1—C4 | 1.464 (2) | C5—H5 | 0.96 (2) |
N1—H1n | 0.90 (2) | C6—C7 | 1.388 (2) |
N1—H2n | 0.92 (2) | C6—H6 | 0.97 (2) |
N1—H3n | 0.91 (2) | C7—H7 | 0.98 (2) |
C1—C2 | 1.487 (2) | | |
| | | |
C1—O1—H | 110 (1) | C2—C3—C4 | 118.6 (1) |
C4—N1—H1n | 105.8 (9) | C2—C3—H3 | 121 (1) |
C4—N1—H2n | 111 (1) | C4—C3—H3 | 120 (1) |
C4—N1—H3n | 109 (1) | N1—C4—C3 | 119.3 (1) |
H1n—N1—H2n | 110 (2) | N1—C4—C5 | 119.1 (1) |
H1n—N1—H3n | 114 (2) | C3—C4—C5 | 121.6 (1) |
H2n—N1—H3n | 106 (2) | C4—C5—C6 | 119.3 (1) |
O3—N2—O4 | 118.2 (1) | C4—C5—H5 | 120.8 (13) |
O3—N2—O5 | 120.5 (1) | C6—C5—H5 | 119.9 (12) |
O4—N2—O5 | 121.3 (1) | C5—C6—C7 | 120.3 (1) |
O1—C1—O2 | 123.6 (1) | C5—C6—H6 | 120 (1) |
O1—C1—C2 | 114.7 (1) | C7—C6—H6 | 119 (1) |
O2—C1—C2 | 121.7 (1) | C2—C7—C6 | 119.8 (1) |
C1—C2—C3 | 120.6 (1) | C2—C7—H7 | 119 (1) |
C1—C2—C7 | 118.9 (1) | C6—C7—H7 | 121 (1) |
C3—C2—C7 | 120.4 (1) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H···O2i | 0.90 (2) | 1.78 (2) | 2.676 (1) | 177 (2) |
N1—H1n···O4ii | 0.90 (2) | 2.03 (2) | 2.883 (2) | 159 (2) |
N1—H3n···O3 | 0.91 (2) | 1.98 (2) | 2.842 (2) | 158 (2) |
N1—H2n···O3iii | 0.92 (2) | 1.97 (2) | 2.849 (2) | 161 (2) |
Symmetry codes: (i) −x+1/2, −y−1/2, −z; (ii) x, −y+1, z−1/2; (iii) x, y−1, z. |