organic compounds
The title compound, C7H8NO2+·H2PO4-·H2O, is an ionic compound consisting of dihydrogenmonophosphate anions, water molecules and p-carboxyphenylammonium cations. The asymmetric unit contains two independent entities, i.e. 2(HOOC-C6H4-NH3+·H2PO4-·H2O). Anions and cations are linked to each other through strong hydrogen bonds, formed by all H atoms covalently bonded to anions, nitrogen, carboxylic groups and water molecules. A three-dimensional complex network of hydrogen bonds ensures the cohesion of the ionic structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001022/cv6076sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001022/cv6076Isup2.hkl |
CCDC reference: 180793
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.058
- Data-to-parameter ratio = 10.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Computing details top
Data collection: CAD-4 Operations Manual (Enraf-Nonius, 1994); cell refinement: CAD-4 Operations Manual; data reduction: OpenMolEN (Nonius, 1997); program(s) used to solve structure: SIR (Burla et al., 1989); program(s) used to refine structure: OpenMolEN (Nonius, 1997); software used to prepare material for publication: OpenMolEN.
p-Carboxyphenyl ammonium dihydrogenmonophosphate hydrate top
Crystal data top
C7H8NO2+·H2PO4−·H2O | Z = 4.0 |
Mr = 253.15 | F(000) = 528 |
Triclinic, P1 | Dx = 1.596 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.517 (2) Å | Cell parameters from 25 reflections |
b = 8.902 (4) Å | θ = 1.4–30.0° |
c = 14.513 (4) Å | µ = 0.28 mm−1 |
α = 106.49 (4)° | T = 294 K |
β = 90.17 (5)° | Plate, orange |
γ = 92.76 (4)° | 0.6 × 0.3 × 0.2 mm |
V = 1053.6 (5) Å3 |
Data collection top
MACH3 diffractometer | θmax = 30.0° |
Radiation source: X-ray_tube | h = −11→11 |
θ/2θ scans | k = −12→12 |
6146 measured reflections | l = −20→0 |
6146 independent reflections | 3 standard reflections every 200 reflections |
3740 reflections with I > 3σ(I) | intensity decay: −1,2% |
Rint = 0.015 |
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)] = 0.039 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.058 | Only H-atom coordinates refined |
S = 1.14 | w = 4Fo2/[σ2(Fo2) + 0.0016 Fo4] |
3740 reflections | (Δ/σ)max = 0.014 |
361 parameters | Δρmax = 0.24 e Å−3 |
24 restraints | Δρmin = −0.37 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1w | 1.0978 (2) | 0.7401 (2) | 0.1100 (1) | 0.0332 (7) | |
O2w | 0.4062 (2) | 0.2456 (2) | 0.1063 (1) | 0.0320 (7) | |
P1b | 0.82631 (7) | 0.23331 (7) | 0.13409 (4) | 0.0275 (2) | |
P1a | 0.67246 (7) | 0.72132 (7) | 0.13677 (4) | 0.0270 (2) | |
O1a | 0.8105 (2) | 0.7791 (2) | 0.2046 (1) | 0.0317 (7) | |
O1B | 0.8950 (2) | 0.3495 (2) | 0.0855 (1) | 0.0327 (7) | |
O2A | 0.6136 (2) | 0.8385 (2) | 0.0891 (1) | 0.0327 (7) | |
O2B | 0.6908 (2) | 0.2895 (2) | 0.1987 (1) | 0.0336 (7) | |
O3a | 0.7172 (2) | 0.5756 (2) | 0.0530 (1) | 0.0378 (8) | |
O3B | 0.7738 (2) | 0.0831 (2) | 0.0511 (1) | 0.0383 (8) | |
O4A | 0.5324 (2) | 0.6653 (2) | 0.1901 (1) | 0.0384 (8) | |
O4b | 0.9609 (2) | 0.1855 (2) | 0.1921 (1) | 0.0390 (8) | |
O5A | 0.0942 (2) | 0.7385 (2) | 0.6217 (1) | 0.0453 (9) | |
O5B | 0.4348 (2) | 1.2418 (2) | 0.6208 (1) | 0.0400 (8) | |
O6B | 0.1993 (2) | 1.1160 (2) | 0.6119 (1) | 0.0379 (8) | |
O6A | 0.2891 (2) | 0.5790 (2) | 0.6187 (1) | 0.0395 (8) | |
N1a | 0.1904 (2) | 0.4749 (2) | 0.1676 (1) | 0.0298 (8) | |
N1b | 0.3345 (2) | 0.9755 (2) | 0.1638 (1) | 0.0285 (8) | |
C1a | 0.1852 (3) | 0.6433 (3) | 0.5775 (1) | 0.0307 (9) | |
C1b | 0.3247 (3) | 1.1625 (3) | 0.5741 (1) | 0.0313 (9) | |
C2a | 0.1866 (3) | 0.5934 (3) | 0.4706 (1) | 0.0288 (9) | |
C2b | 0.3248 (3) | 1.1106 (2) | 0.4670 (1) | 0.0281 (9) | |
C3b | 0.1903 (3) | 1.0467 (3) | 0.4140 (2) | 0.034 (1) | |
C3a | 0.0716 (3) | 0.6441 (3) | 0.4203 (2) | 0.037 (1) | |
C4a | 0.0714 (3) | 0.6032 (3) | 0.3207 (1) | 0.037 (1) | |
C4b | 0.1934 (3) | 1.0028 (3) | 0.3142 (1) | 0.032 (1) | |
C5a | 0.1887 (3) | 0.5147 (2) | 0.2727 (1) | 0.0268 (9) | |
C5b | 0.3318 (3) | 1.0216 (2) | 0.2687 (1) | 0.0267 (8) | |
C6b | 0.4673 (3) | 1.0842 (3) | 0.3208 (1) | 0.033 (1) | |
C6a | 0.3029 (3) | 0.4606 (3) | 0.3207 (2) | 0.033 (1) | |
C7a | 0.3007 (3) | 0.5004 (3) | 0.4203 (2) | 0.034 (1) | |
C7b | 0.4636 (3) | 1.1290 (3) | 0.4200 (1) | 0.032 (1) | |
H1nb | 0.431 (3) | 0.927 (3) | 0.143 (2) | 0.0399* | |
H1b | 0.196 (3) | 1.137 (3) | 0.677 (2) | 0.0573* | |
H1na | 0.191 (3) | 0.551 (3) | 0.152 (2) | 0.0404* | |
H1a | 0.303 (3) | 0.649 (3) | 0.684 (2) | 0.0559* | |
H2na | 0.277 (3) | 0.422 (3) | 0.140 (2) | 0.0404* | |
H2nb | 0.338 (3) | 1.062 (3) | 0.140 (2) | 0.0399* | |
H3b | 0.099 (3) | 1.033 (3) | 0.445 (2) | 0.0482* | |
H03a | 0.763 (3) | 0.514 (3) | 0.068 (2) | 0.0522* | |
H03b | 0.716 (3) | −0.004 (3) | 0.072 (2) | 0.0535* | |
H3nb | 0.249 (3) | 0.902 (3) | 0.144 (2) | 0.0399* | |
H3na | 0.104 (3) | 0.424 (3) | 0.142 (2) | 0.0404* | |
H3a | 0.009 (3) | 0.706 (3) | 0.456 (2) | 0.0511* | |
H04a | 0.539 (3) | 0.693 (3) | 0.244 (2) | 0.0532* | |
H04b | 0.923 (3) | 0.200 (3) | 0.244 (2) | 0.0538* | |
H4a | −0.020 (3) | 0.642 (3) | 0.282 (2) | 0.0502* | |
H4b | 0.103 (3) | 0.971 (3) | 0.276 (2) | 0.0465* | |
H6b | 0.580 (3) | 1.092 (3) | 0.292 (2) | 0.0453* | |
H6a | 0.377 (3) | 0.397 (3) | 0.283 (2) | 0.0448* | |
H7a | 0.370 (3) | 0.465 (3) | 0.453 (2) | 0.0450* | |
H7b | 0.557 (3) | 1.187 (3) | 0.458 (2) | 0.0452* | |
H1w1 | 0.999 (3) | 0.771 (3) | 0.140 (2) | 0.0459* | |
H1w2 | 0.410 (3) | 0.239 (3) | 0.046 (2) | 0.0441* | |
H2w1 | 1.082 (3) | 0.730 (3) | 0.055 (2) | 0.0459* | |
H2w2 | 0.487 (3) | 0.278 (3) | 0.129 (2) | 0.0441* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1w | 0.0360 (8) | 0.0484 (8) | 0.0210 (6) | 0.0013 (7) | 0.0021 (6) | 0.0093 (6) |
O2w | 0.0335 (7) | 0.0461 (8) | 0.0212 (6) | 0.0039 (7) | −0.0007 (6) | 0.0085 (6) |
P1b | 0.0323 (3) | 0.0362 (2) | 0.0177 (2) | −0.0006 (2) | −0.0004 (2) | 0.0090 (2) |
P1a | 0.0313 (2) | 0.0352 (2) | 0.0179 (2) | 0.0035 (2) | 0.0011 (2) | 0.0084 (2) |
O1a | 0.0290 (7) | 0.0560 (9) | 0.0195 (6) | 0.0024 (7) | 0.0003 (6) | 0.0105 (6) |
O1b | 0.0381 (8) | 0.0372 (7) | 0.0246 (6) | −0.0001 (6) | 0.0016 (6) | 0.0118 (5) |
O2a | 0.0367 (8) | 0.0368 (7) | 0.0260 (6) | 0.0061 (6) | 0.0010 (6) | 0.0118 (5) |
O2b | 0.0309 (7) | 0.0575 (9) | 0.0213 (6) | 0.0027 (7) | −0.0003 (6) | 0.0095 (6) |
O3a | 0.0556 (9) | 0.0400 (8) | 0.0242 (7) | 0.0169 (7) | −0.0010 (7) | 0.0062 (6) |
O3b | 0.056 (1) | 0.0402 (8) | 0.0247 (7) | −0.0100 (8) | −0.0014 (7) | 0.0076 (6) |
O4a | 0.0423 (9) | 0.0574 (9) | 0.0233 (6) | −0.0119 (8) | −0.0000 (6) | 0.0128 (6) |
O4b | 0.0440 (9) | 0.0588 (9) | 0.0228 (6) | 0.0140 (7) | −0.0003 (6) | 0.0137 (6) |
O5a | 0.067 (1) | 0.0611 (9) | 0.0226 (7) | 0.0279 (8) | 0.0030 (7) | 0.0103 (6) |
O5b | 0.052 (1) | 0.060 (1) | 0.0207 (6) | −0.0143 (8) | −0.0020 (7) | 0.0088 (6) |
O6b | 0.0376 (8) | 0.071 (1) | 0.0204 (6) | −0.0008 (8) | 0.0036 (6) | 0.0095 (7) |
O6a | 0.0451 (9) | 0.0600 (9) | 0.0227 (6) | 0.0122 (8) | −0.0027 (7) | 0.0086 (6) |
N1a | 0.0360 (9) | 0.0363 (8) | 0.0202 (7) | 0.0011 (8) | 0.0002 (7) | 0.0076 (6) |
N1b | 0.0360 (9) | 0.0392 (9) | 0.0165 (6) | 0.0024 (8) | 0.0020 (7) | 0.0061 (6) |
C1a | 0.035 (1) | 0.038 (1) | 0.0218 (8) | 0.0015 (9) | −0.0024 (8) | 0.0100 (7) |
C1b | 0.038 (1) | 0.037 (1) | 0.0222 (8) | 0.0055 (9) | 0.0025 (8) | 0.0100 (7) |
C2a | 0.032 (1) | 0.0369 (9) | 0.0200 (7) | 0.0001 (8) | −0.0007 (7) | 0.0088 (7) |
C2b | 0.038 (1) | 0.0324 (9) | 0.0181 (7) | 0.0040 (8) | 0.0021 (8) | 0.0065 (7) |
C3b | 0.031 (1) | 0.053 (1) | 0.0234 (8) | 0.001 (1) | 0.0056 (8) | 0.0072 (8) |
C3a | 0.046 (1) | 0.051 (1) | 0.0223 (8) | 0.021 (1) | 0.0058 (9) | 0.0096 (8) |
C4a | 0.044 (1) | 0.051 (1) | 0.0229 (8) | 0.018 (1) | 0.0005 (9) | 0.0110 (8) |
C4b | 0.032 (1) | 0.049 (1) | 0.0217 (9) | 0.002 (1) | −0.0002 (8) | 0.0031 (8) |
C5a | 0.031 (1) | 0.0335 (9) | 0.0183 (7) | −0.0008 (8) | −0.0014 (7) | 0.0067 (7) |
C5b | 0.033 (1) | 0.0316 (9) | 0.0183 (7) | 0.0047 (8) | 0.0015 (7) | 0.0087 (6) |
C6b | 0.035 (1) | 0.045 (1) | 0.0222 (8) | −0.0039 (9) | 0.0031 (8) | 0.0105 (7) |
C6a | 0.034 (1) | 0.044 (1) | 0.0247 (9) | 0.0098 (9) | −0.0014 (8) | 0.0048 (8) |
C7a | 0.035 (1) | 0.046 (1) | 0.0248 (9) | 0.0085 (9) | −0.0054 (8) | 0.0074 (8) |
C7b | 0.034 (1) | 0.043 (1) | 0.0234 (8) | −0.0036 (9) | −0.0006 (8) | 0.0084 (8) |
Geometric parameters (Å, º) top
O1w—H1w1 | 0.97 (3) | N1b—C5b | 1.460 (2) |
O1w—H2w1 | 0.78 (3) | N1b—H1nb | 0.96 (3) |
O2w—H1w2 | 0.87 (3) | N1b—H2nb | 0.93 (3) |
O2w—H2w2 | 0.77 (2) | N1b—H3nb | 0.94 (2) |
P1b—O1b | 1.506 (2) | C1a—C2a | 1.488 (3) |
P1b—O2b | 1.502 (2) | C1b—C2b | 1.491 (3) |
P1b—O3b | 1.569 (1) | C2a—C3a | 1.386 (4) |
P1b—O4b | 1.564 (2) | C2a—C7a | 1.379 (3) |
P1a—O1a | 1.505 (1) | C2b—C3b | 1.382 (3) |
P1a—O2a | 1.509 (2) | C2b—C7b | 1.393 (3) |
P1a—O3a | 1.568 (1) | C3b—C4b | 1.390 (3) |
P1a—O4a | 1.561 (2) | C3b—H3b | 0.92 (3) |
O3a—H03a | 0.77 (3) | C3a—C4a | 1.387 (3) |
O3b—H03b | 1.02 (3) | C3a—H3a | 0.86 (2) |
O4a—H04a | 0.75 (3) | C4a—C5a | 1.368 (3) |
O4b—H04b | 0.80 (3) | C4a—H4a | 1.08 (3) |
O5a—C1a | 1.220 (3) | C4b—C5b | 1.379 (3) |
O5b—C1b | 1.224 (3) | C4b—H4b | 0.93 (3) |
O6b—C1b | 1.305 (3) | C5a—C6a | 1.376 (3) |
O6b—H1b | 0.92 (3) | C5b—C6b | 1.381 (3) |
O6a—C1a | 1.307 (3) | C6b—C7b | 1.381 (3) |
O6a—H1a | 0.98 (2) | C6b—H6b | 1.06 (3) |
N1a—C5a | 1.465 (3) | C6a—C7a | 1.388 (3) |
N1a—H1na | 0.78 (3) | C6a—H6a | 0.93 (2) |
N1a—H2na | 0.92 (2) | C7a—H7a | 0.89 (3) |
N1a—H3na | 0.87 (2) | C7b—H7b | 1.00 (2) |
H1w1—O1w—H2w1 | 104 (2) | O6b—C1b—C2b | 114.3 (2) |
H1w2—O2w—H2w2 | 107 (2) | C1a—C2a—C3a | 119.1 (2) |
O1b—P1b—O2b | 115.0 (1) | C1a—C2a—C7a | 121.8 (2) |
O1b—P1b—O3b | 105.92 (9) | C3a—C2a—C7a | 119.1 (2) |
O1b—P1b—O4b | 108.3 (1) | C1b—C2b—C3b | 121.4 (2) |
O2b—P1b—O3b | 110.42 (9) | C1b—C2b—C7b | 118.8 (2) |
O2b—P1b—O4b | 110.00 (9) | C3b—C2b—C7b | 119.7 (2) |
O3b—P1b—O4b | 106.9 (1) | C2b—C3b—C4b | 120.0 (2) |
O1a—P1a—O2a | 115.2 (1) | C2b—C3b—H3b | 119 (1) |
O1a—P1a—O3a | 110.06 (9) | C4b—C3b—H3b | 120 (1) |
O1a—P1a—O4a | 110.22 (9) | C2a—C3a—C4a | 120.7 (2) |
O2a—P1a—O3a | 105.90 (9) | C2a—C3a—H3a | 113 (1) |
O2a—P1a—O4a | 108.2 (1) | C4a—C3a—H3a | 125 (1) |
O3a—P1a—O4a | 106.78 (9) | C3a—C4a—C5a | 118.9 (2) |
P1a—O3a—H03a | 115 (1) | C3a—C4a—H4a | 120 (1) |
P1b—O3b—H03b | 115 (1) | C5a—C4a—H4a | 120 (1) |
P1a—O4a—H04a | 115 (2) | C3b—C4b—C5b | 119.5 (2) |
P1b—O4b—H04b | 101 (2) | C3b—C4b—H4b | 122 (1) |
C1b—O6b—H1b | 118 (1) | C5b—C4b—H4b | 117 (1) |
C1a—O6a—H1a | 105 (1) | N1a—C5a—C4a | 118.9 (2) |
C5a—N1a—H1na | 109 (1) | N1a—C5a—C6a | 119.5 (2) |
C5a—N1a—H2na | 114 (1) | C4a—C5a—C6a | 121.6 (2) |
C5a—N1a—H3na | 111 (1) | N1b—C5b—C4b | 119.4 (2) |
H1na—N1a—H2na | 106 (2) | N1b—C5b—C6b | 119.6 (2) |
H1na—N1a—H3na | 104 (2) | C4b—C5b—C6b | 121.0 (2) |
H2na—N1a—H3na | 110 (2) | C5b—C6b—C7b | 119.3 (2) |
C5b—N1b—H1nb | 109 (1) | C5b—C6b—H6b | 125 (1) |
C5b—N1b—H2nb | 111 (1) | C7b—C6b—H6b | 114 (1) |
C5b—N1b—H3nb | 105 (1) | C5a—C6a—C7a | 118.9 (2) |
H1nb—N1b—H2nb | 103 (2) | C5a—C6a—H6a | 117 (1) |
H1nb—N1b—H3nb | 110 (2) | C7a—C6a—H6a | 123 (1) |
H2nb—N1b—H3nb | 116 (2) | C2a—C7a—C6a | 120.6 (2) |
O5a—C1a—O6a | 123.8 (2) | C2a—C7a—H7a | 117 (1) |
O5a—C1a—C2a | 121.4 (2) | C6a—C7a—H7a | 121 (1) |
O6a—C1a—C2a | 114.8 (2) | C2b—C7b—C6b | 120.3 (2) |
O5b—C1b—O6b | 124.1 (2) | C2b—C7b—H7b | 119 (1) |
O5b—C1b—C2b | 121.5 (2) | C6b—C7b—H7b | 119 (1) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3a—H03a···O1b | 0.77 (3) | 1.96 (3) | 2.720 (2) | 171 (3) |
O3b—H03b···O2ai | 1.02 (3) | 1.69 (3) | 2.704 (2) | 171 (3) |
O1w—H2w1···O1bii | 0.79 (3) | 1.97 (3) | 2.723 (2) | 159 (3) |
O2w—H2w2···O2b | 0.77 (3) | 1.99 (3) | 2.724 (2) | 160 (3) |
O2w—H1w2···O2aiii | 0.86 (3) | 1.89 (3) | 2.722 (2) | 162 (3) |
O1w—H1w1···O1a | 0.96 (3) | 1.86 (3) | 2.797 (2) | 165 (2) |
N1a—H3na···O1biv | 0.87 (3) | 1.96 (3) | 2.819 (2) | 169 (3) |
N1b—H1nb···O2a | 0.96 (3) | 1.85 (3) | 2.803 (2) | 173 (2) |
O6b—H1b···O1av | 0.91 (3) | 1.67 (3) | 2.563 (2) | 166 (3) |
O6a—H1a···O2bvi | 0.98 (3) | 1.63 (3) | 2.577 (2) | 161 (3) |
O4b—H04b···O5avi | 0.80 (3) | 1.88 (3) | 2.643 (2) | 160 (3) |
O4a—H04a···O5bv | 0.75 (3) | 1.89 (3) | 2.641 (2) | 177 (3) |
N1a—H2na···O2w | 0.92 (3) | 1.91 (3) | 2.770 (2) | 154 (2) |
N1a—H1na···O1wiv | 0.77 (3) | 2.13 (3) | 2.862 (3) | 158 (3) |
N1b—H2nb···O2wvii | 0.93 (3) | 1.90 (3) | 2.802 (3) | 163 (2) |
N1b—H3nb···O1wiv | 0.94 (3) | 1.84 (3) | 2.778 (2) | 173 (2) |
Symmetry codes: (i) x, y−1, z; (ii) −x+2, −y+1, −z; (iii) −x+1, −y+1, −z; (iv) x−1, y, z; (v) −x+1, −y+2, −z+1; (vi) −x+1, −y+1, −z+1; (vii) x, y+1, z. |