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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001022/cv6076sup1.cif
Contains datablocks P-AAB-H2PO4, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001022/cv6076Isup2.hkl
Contains datablock I

CCDC reference: 180793

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](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·H2OZ = 4.0
Mr = 253.15F(000) = 528
Triclinic, P1Dx = 1.596 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.517 (2) ÅCell parameters from 25 reflections
b = 8.902 (4) Åθ = 1.4–30.0°
c = 14.513 (4) ŵ = 0.28 mm1
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_tubeh = 1111
θ/2θ scansk = 1212
6146 measured reflectionsl = 200
6146 independent reflections3 standard reflections every 200 reflections
3740 reflections with I > 3σ(I) intensity decay: 1,2%
Rint = 0.015
Refinement top
Refinement on FPrimary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.058Only H-atom coordinates refined
S = 1.14 w = 4Fo2/[σ2(Fo2) + 0.0016 Fo4]
3740 reflections(Δ/σ)max = 0.014
361 parametersΔρmax = 0.24 e Å3
24 restraintsΔρmin = 0.37 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1w1.0978 (2)0.7401 (2)0.1100 (1)0.0332 (7)
O2w0.4062 (2)0.2456 (2)0.1063 (1)0.0320 (7)
P1b0.82631 (7)0.23331 (7)0.13409 (4)0.0275 (2)
P1a0.67246 (7)0.72132 (7)0.13677 (4)0.0270 (2)
O1a0.8105 (2)0.7791 (2)0.2046 (1)0.0317 (7)
O1B0.8950 (2)0.3495 (2)0.0855 (1)0.0327 (7)
O2A0.6136 (2)0.8385 (2)0.0891 (1)0.0327 (7)
O2B0.6908 (2)0.2895 (2)0.1987 (1)0.0336 (7)
O3a0.7172 (2)0.5756 (2)0.0530 (1)0.0378 (8)
O3B0.7738 (2)0.0831 (2)0.0511 (1)0.0383 (8)
O4A0.5324 (2)0.6653 (2)0.1901 (1)0.0384 (8)
O4b0.9609 (2)0.1855 (2)0.1921 (1)0.0390 (8)
O5A0.0942 (2)0.7385 (2)0.6217 (1)0.0453 (9)
O5B0.4348 (2)1.2418 (2)0.6208 (1)0.0400 (8)
O6B0.1993 (2)1.1160 (2)0.6119 (1)0.0379 (8)
O6A0.2891 (2)0.5790 (2)0.6187 (1)0.0395 (8)
N1a0.1904 (2)0.4749 (2)0.1676 (1)0.0298 (8)
N1b0.3345 (2)0.9755 (2)0.1638 (1)0.0285 (8)
C1a0.1852 (3)0.6433 (3)0.5775 (1)0.0307 (9)
C1b0.3247 (3)1.1625 (3)0.5741 (1)0.0313 (9)
C2a0.1866 (3)0.5934 (3)0.4706 (1)0.0288 (9)
C2b0.3248 (3)1.1106 (2)0.4670 (1)0.0281 (9)
C3b0.1903 (3)1.0467 (3)0.4140 (2)0.034 (1)
C3a0.0716 (3)0.6441 (3)0.4203 (2)0.037 (1)
C4a0.0714 (3)0.6032 (3)0.3207 (1)0.037 (1)
C4b0.1934 (3)1.0028 (3)0.3142 (1)0.032 (1)
C5a0.1887 (3)0.5147 (2)0.2727 (1)0.0268 (9)
C5b0.3318 (3)1.0216 (2)0.2687 (1)0.0267 (8)
C6b0.4673 (3)1.0842 (3)0.3208 (1)0.033 (1)
C6a0.3029 (3)0.4606 (3)0.3207 (2)0.033 (1)
C7a0.3007 (3)0.5004 (3)0.4203 (2)0.034 (1)
C7b0.4636 (3)1.1290 (3)0.4200 (1)0.032 (1)
H1nb0.431 (3)0.927 (3)0.143 (2)0.0399*
H1b0.196 (3)1.137 (3)0.677 (2)0.0573*
H1na0.191 (3)0.551 (3)0.152 (2)0.0404*
H1a0.303 (3)0.649 (3)0.684 (2)0.0559*
H2na0.277 (3)0.422 (3)0.140 (2)0.0404*
H2nb0.338 (3)1.062 (3)0.140 (2)0.0399*
H3b0.099 (3)1.033 (3)0.445 (2)0.0482*
H03a0.763 (3)0.514 (3)0.068 (2)0.0522*
H03b0.716 (3)0.004 (3)0.072 (2)0.0535*
H3nb0.249 (3)0.902 (3)0.144 (2)0.0399*
H3na0.104 (3)0.424 (3)0.142 (2)0.0404*
H3a0.009 (3)0.706 (3)0.456 (2)0.0511*
H04a0.539 (3)0.693 (3)0.244 (2)0.0532*
H04b0.923 (3)0.200 (3)0.244 (2)0.0538*
H4a0.020 (3)0.642 (3)0.282 (2)0.0502*
H4b0.103 (3)0.971 (3)0.276 (2)0.0465*
H6b0.580 (3)1.092 (3)0.292 (2)0.0453*
H6a0.377 (3)0.397 (3)0.283 (2)0.0448*
H7a0.370 (3)0.465 (3)0.453 (2)0.0450*
H7b0.557 (3)1.187 (3)0.458 (2)0.0452*
H1w10.999 (3)0.771 (3)0.140 (2)0.0459*
H1w20.410 (3)0.239 (3)0.046 (2)0.0441*
H2w11.082 (3)0.730 (3)0.055 (2)0.0459*
H2w20.487 (3)0.278 (3)0.129 (2)0.0441*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1w0.0360 (8)0.0484 (8)0.0210 (6)0.0013 (7)0.0021 (6)0.0093 (6)
O2w0.0335 (7)0.0461 (8)0.0212 (6)0.0039 (7)0.0007 (6)0.0085 (6)
P1b0.0323 (3)0.0362 (2)0.0177 (2)0.0006 (2)0.0004 (2)0.0090 (2)
P1a0.0313 (2)0.0352 (2)0.0179 (2)0.0035 (2)0.0011 (2)0.0084 (2)
O1a0.0290 (7)0.0560 (9)0.0195 (6)0.0024 (7)0.0003 (6)0.0105 (6)
O1b0.0381 (8)0.0372 (7)0.0246 (6)0.0001 (6)0.0016 (6)0.0118 (5)
O2a0.0367 (8)0.0368 (7)0.0260 (6)0.0061 (6)0.0010 (6)0.0118 (5)
O2b0.0309 (7)0.0575 (9)0.0213 (6)0.0027 (7)0.0003 (6)0.0095 (6)
O3a0.0556 (9)0.0400 (8)0.0242 (7)0.0169 (7)0.0010 (7)0.0062 (6)
O3b0.056 (1)0.0402 (8)0.0247 (7)0.0100 (8)0.0014 (7)0.0076 (6)
O4a0.0423 (9)0.0574 (9)0.0233 (6)0.0119 (8)0.0000 (6)0.0128 (6)
O4b0.0440 (9)0.0588 (9)0.0228 (6)0.0140 (7)0.0003 (6)0.0137 (6)
O5a0.067 (1)0.0611 (9)0.0226 (7)0.0279 (8)0.0030 (7)0.0103 (6)
O5b0.052 (1)0.060 (1)0.0207 (6)0.0143 (8)0.0020 (7)0.0088 (6)
O6b0.0376 (8)0.071 (1)0.0204 (6)0.0008 (8)0.0036 (6)0.0095 (7)
O6a0.0451 (9)0.0600 (9)0.0227 (6)0.0122 (8)0.0027 (7)0.0086 (6)
N1a0.0360 (9)0.0363 (8)0.0202 (7)0.0011 (8)0.0002 (7)0.0076 (6)
N1b0.0360 (9)0.0392 (9)0.0165 (6)0.0024 (8)0.0020 (7)0.0061 (6)
C1a0.035 (1)0.038 (1)0.0218 (8)0.0015 (9)0.0024 (8)0.0100 (7)
C1b0.038 (1)0.037 (1)0.0222 (8)0.0055 (9)0.0025 (8)0.0100 (7)
C2a0.032 (1)0.0369 (9)0.0200 (7)0.0001 (8)0.0007 (7)0.0088 (7)
C2b0.038 (1)0.0324 (9)0.0181 (7)0.0040 (8)0.0021 (8)0.0065 (7)
C3b0.031 (1)0.053 (1)0.0234 (8)0.001 (1)0.0056 (8)0.0072 (8)
C3a0.046 (1)0.051 (1)0.0223 (8)0.021 (1)0.0058 (9)0.0096 (8)
C4a0.044 (1)0.051 (1)0.0229 (8)0.018 (1)0.0005 (9)0.0110 (8)
C4b0.032 (1)0.049 (1)0.0217 (9)0.002 (1)0.0002 (8)0.0031 (8)
C5a0.031 (1)0.0335 (9)0.0183 (7)0.0008 (8)0.0014 (7)0.0067 (7)
C5b0.033 (1)0.0316 (9)0.0183 (7)0.0047 (8)0.0015 (7)0.0087 (6)
C6b0.035 (1)0.045 (1)0.0222 (8)0.0039 (9)0.0031 (8)0.0105 (7)
C6a0.034 (1)0.044 (1)0.0247 (9)0.0098 (9)0.0014 (8)0.0048 (8)
C7a0.035 (1)0.046 (1)0.0248 (9)0.0085 (9)0.0054 (8)0.0074 (8)
C7b0.034 (1)0.043 (1)0.0234 (8)0.0036 (9)0.0006 (8)0.0084 (8)
Geometric parameters (Å, º) top
O1w—H1w10.97 (3)N1b—C5b1.460 (2)
O1w—H2w10.78 (3)N1b—H1nb0.96 (3)
O2w—H1w20.87 (3)N1b—H2nb0.93 (3)
O2w—H2w20.77 (2)N1b—H3nb0.94 (2)
P1b—O1b1.506 (2)C1a—C2a1.488 (3)
P1b—O2b1.502 (2)C1b—C2b1.491 (3)
P1b—O3b1.569 (1)C2a—C3a1.386 (4)
P1b—O4b1.564 (2)C2a—C7a1.379 (3)
P1a—O1a1.505 (1)C2b—C3b1.382 (3)
P1a—O2a1.509 (2)C2b—C7b1.393 (3)
P1a—O3a1.568 (1)C3b—C4b1.390 (3)
P1a—O4a1.561 (2)C3b—H3b0.92 (3)
O3a—H03a0.77 (3)C3a—C4a1.387 (3)
O3b—H03b1.02 (3)C3a—H3a0.86 (2)
O4a—H04a0.75 (3)C4a—C5a1.368 (3)
O4b—H04b0.80 (3)C4a—H4a1.08 (3)
O5a—C1a1.220 (3)C4b—C5b1.379 (3)
O5b—C1b1.224 (3)C4b—H4b0.93 (3)
O6b—C1b1.305 (3)C5a—C6a1.376 (3)
O6b—H1b0.92 (3)C5b—C6b1.381 (3)
O6a—C1a1.307 (3)C6b—C7b1.381 (3)
O6a—H1a0.98 (2)C6b—H6b1.06 (3)
N1a—C5a1.465 (3)C6a—C7a1.388 (3)
N1a—H1na0.78 (3)C6a—H6a0.93 (2)
N1a—H2na0.92 (2)C7a—H7a0.89 (3)
N1a—H3na0.87 (2)C7b—H7b1.00 (2)
H1w1—O1w—H2w1104 (2)O6b—C1b—C2b114.3 (2)
H1w2—O2w—H2w2107 (2)C1a—C2a—C3a119.1 (2)
O1b—P1b—O2b115.0 (1)C1a—C2a—C7a121.8 (2)
O1b—P1b—O3b105.92 (9)C3a—C2a—C7a119.1 (2)
O1b—P1b—O4b108.3 (1)C1b—C2b—C3b121.4 (2)
O2b—P1b—O3b110.42 (9)C1b—C2b—C7b118.8 (2)
O2b—P1b—O4b110.00 (9)C3b—C2b—C7b119.7 (2)
O3b—P1b—O4b106.9 (1)C2b—C3b—C4b120.0 (2)
O1a—P1a—O2a115.2 (1)C2b—C3b—H3b119 (1)
O1a—P1a—O3a110.06 (9)C4b—C3b—H3b120 (1)
O1a—P1a—O4a110.22 (9)C2a—C3a—C4a120.7 (2)
O2a—P1a—O3a105.90 (9)C2a—C3a—H3a113 (1)
O2a—P1a—O4a108.2 (1)C4a—C3a—H3a125 (1)
O3a—P1a—O4a106.78 (9)C3a—C4a—C5a118.9 (2)
P1a—O3a—H03a115 (1)C3a—C4a—H4a120 (1)
P1b—O3b—H03b115 (1)C5a—C4a—H4a120 (1)
P1a—O4a—H04a115 (2)C3b—C4b—C5b119.5 (2)
P1b—O4b—H04b101 (2)C3b—C4b—H4b122 (1)
C1b—O6b—H1b118 (1)C5b—C4b—H4b117 (1)
C1a—O6a—H1a105 (1)N1a—C5a—C4a118.9 (2)
C5a—N1a—H1na109 (1)N1a—C5a—C6a119.5 (2)
C5a—N1a—H2na114 (1)C4a—C5a—C6a121.6 (2)
C5a—N1a—H3na111 (1)N1b—C5b—C4b119.4 (2)
H1na—N1a—H2na106 (2)N1b—C5b—C6b119.6 (2)
H1na—N1a—H3na104 (2)C4b—C5b—C6b121.0 (2)
H2na—N1a—H3na110 (2)C5b—C6b—C7b119.3 (2)
C5b—N1b—H1nb109 (1)C5b—C6b—H6b125 (1)
C5b—N1b—H2nb111 (1)C7b—C6b—H6b114 (1)
C5b—N1b—H3nb105 (1)C5a—C6a—C7a118.9 (2)
H1nb—N1b—H2nb103 (2)C5a—C6a—H6a117 (1)
H1nb—N1b—H3nb110 (2)C7a—C6a—H6a123 (1)
H2nb—N1b—H3nb116 (2)C2a—C7a—C6a120.6 (2)
O5a—C1a—O6a123.8 (2)C2a—C7a—H7a117 (1)
O5a—C1a—C2a121.4 (2)C6a—C7a—H7a121 (1)
O6a—C1a—C2a114.8 (2)C2b—C7b—C6b120.3 (2)
O5b—C1b—O6b124.1 (2)C2b—C7b—H7b119 (1)
O5b—C1b—C2b121.5 (2)C6b—C7b—H7b119 (1)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3a—H03a···O1b0.77 (3)1.96 (3)2.720 (2)171 (3)
O3b—H03b···O2ai1.02 (3)1.69 (3)2.704 (2)171 (3)
O1w—H2w1···O1bii0.79 (3)1.97 (3)2.723 (2)159 (3)
O2w—H2w2···O2b0.77 (3)1.99 (3)2.724 (2)160 (3)
O2w—H1w2···O2aiii0.86 (3)1.89 (3)2.722 (2)162 (3)
O1w—H1w1···O1a0.96 (3)1.86 (3)2.797 (2)165 (2)
N1a—H3na···O1biv0.87 (3)1.96 (3)2.819 (2)169 (3)
N1b—H1nb···O2a0.96 (3)1.85 (3)2.803 (2)173 (2)
O6b—H1b···O1av0.91 (3)1.67 (3)2.563 (2)166 (3)
O6a—H1a···O2bvi0.98 (3)1.63 (3)2.577 (2)161 (3)
O4b—H04b···O5avi0.80 (3)1.88 (3)2.643 (2)160 (3)
O4a—H04a···O5bv0.75 (3)1.89 (3)2.641 (2)177 (3)
N1a—H2na···O2w0.92 (3)1.91 (3)2.770 (2)154 (2)
N1a—H1na···O1wiv0.77 (3)2.13 (3)2.862 (3)158 (3)
N1b—H2nb···O2wvii0.93 (3)1.90 (3)2.802 (3)163 (2)
N1b—H3nb···O1wiv0.94 (3)1.84 (3)2.778 (2)173 (2)
Symmetry codes: (i) x, y1, z; (ii) x+2, y+1, z; (iii) x+1, y+1, z; (iv) x1, y, z; (v) x+1, y+2, z+1; (vi) x+1, y+1, z+1; (vii) x, y+1, z.
 

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