p-Carboxy­phenyl­ammonium di­hydro­gen­mono­phosphate monohydrate

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.

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

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Computing details

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

Crystal data

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) Å^3

Data collection

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

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: difference Fourier map
wR(F^2) = 0.058	Only H-atom coordinates refined
S = 1.14	w = 4Fo^2/[σ^2(Fo^2) + 0.0016 Fo^4]
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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O2a^i	1.02 (3)	1.69 (3)	2.704 (2)	171 (3)
O1w—H2w1···O1b^ii	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···O2a^iii	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···O1b^iv	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···O1a^v	0.91 (3)	1.67 (3)	2.563 (2)	166 (3)
O6a—H1a···O2b^vi	0.98 (3)	1.63 (3)	2.577 (2)	161 (3)
O4b—H04b···O5a^vi	0.80 (3)	1.88 (3)	2.643 (2)	160 (3)
O4a—H04a···O5b^v	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···O1w^iv	0.77 (3)	2.13 (3)	2.862 (3)	158 (3)
N1b—H2nb···O2w^vii	0.93 (3)	1.90 (3)	2.802 (3)	163 (2)
N1b—H3nb···O1w^iv	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.