5-Carb-oxy-2,4-dihy-droxy-anilinium chloride dihydrate.

In the title compound, C(7)H(8)NO(4) (+)·Cl(-)·2H(2)O, the organic mol-ecule is almost planar with an r.m.s. deviation of 0.0164 Å for all non-H atoms. An S(6) ring motif is formed due to an intra-molecular O-H⋯O hydrogen bond. In the crystal, the mol-ecules are linked into a three-dimensional network by N-H⋯Cl, N-H⋯O, O-H⋯Cl and O-H⋯O hydrogen bonds.

Related literature

For a related structure, see: Naz et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C7H8NO4 +·Cl−·2H2O

M = 241.63

Triclinic,

a = 6.0285 (8) Å

b = 7.9597 (8) Å

c = 10.9570 (13) Å

α = 100.135 (5)°

β = 97.162 (4)°

γ = 92.921 (5)°

V = 512.10 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 296 K

0.28 × 0.15 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.935, T max = 0.965

8850 measured reflections

2548 independent reflections

1853 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.115

S = 1.03

2548 reflections

139 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000559/dn2650sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000559/dn2650Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H8NO4+·Cl−·2H2O	Z = 2
Mr = 241.63	F(000) = 252
Triclinic, P1	Dx = 1.567 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0285 (8) Å	Cell parameters from 1853 reflections
b = 7.9597 (8) Å	θ = 1.9–28.4°
c = 10.9570 (13) Å	µ = 0.38 mm−1
α = 100.135 (5)°	T = 296 K
β = 97.162 (4)°	Needle, brown
γ = 92.921 (5)°	0.28 × 0.15 × 0.10 mm
V = 512.10 (11) Å3

Bruker Kappa APEXII CCD diffractometer	2548 independent reflections
Radiation source: fine-focus sealed tube	1853 reflections with I > 2σ(I)
graphite	Rint = 0.039
Detector resolution: 7.50 pixels mm-1	θmax = 28.4°, θmin = 1.9°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→8
Tmin = 0.935, Tmax = 0.965	l = −14→14
8850 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0571P)2 + 0.0225P] where P = (Fo2 + 2Fc2)/3
2548 reflections	(Δ/σ)max < 0.001
139 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

	x	y	z	Uiso*/Ueq
O1	0.2807 (3)	0.0789 (2)	0.38672 (13)	0.0395 (4)
H1	0.3127	0.0453	0.3164	0.059*
O2	−0.0155 (3)	0.1663 (2)	0.27792 (13)	0.0454 (4)
O3	−0.2957 (3)	0.35281 (19)	0.40596 (13)	0.0401 (4)
H3	−0.2501	0.3044	0.3424	0.060*
O4	−0.1327 (3)	0.4424 (2)	0.84841 (13)	0.0415 (4)
H4A	−0.2380	0.5033	0.8442	0.062*
N1	0.2345 (3)	0.2711 (2)	0.84317 (14)	0.0306 (4)
H1A	0.3302	0.1906	0.8294	0.046*
H1B	0.1449	0.2439	0.8965	0.046*
H1C	0.3104	0.3712	0.8755	0.046*
C1	0.0937 (4)	0.1574 (2)	0.37826 (18)	0.0303 (5)
C2	0.0302 (3)	0.2322 (2)	0.50004 (17)	0.0268 (4)
C3	−0.1622 (4)	0.3252 (2)	0.50731 (18)	0.0284 (4)
C4	−0.2215 (3)	0.3963 (2)	0.62285 (18)	0.0303 (5)
H4	−0.3489	0.4570	0.6270	0.036*
C5	−0.0912 (3)	0.3766 (2)	0.73114 (18)	0.0286 (5)
C6	0.0990 (3)	0.2839 (2)	0.72445 (17)	0.0248 (4)
C7	0.1595 (3)	0.2145 (2)	0.61147 (17)	0.0259 (4)
H7	0.2879	0.1547	0.6086	0.031*
O5	0.9425 (3)	0.17641 (17)	0.00957 (13)	0.0372 (4)
H5A	0.9959	0.1488	0.0794	0.056*
H5B	0.8641	0.2602	0.0303	0.056*
O6	0.4319 (3)	−0.02049 (19)	0.16590 (14)	0.0427 (4)
H6A	0.4697	0.0818	0.1525	0.064*
H6B	0.3236	−0.0641	0.1078	0.064*
Cl1	0.53107 (9)	0.35035 (6)	0.11554 (5)	0.03442 (17)

	U11	U22	U33	U12	U13	U23
O1	0.0407 (10)	0.0515 (9)	0.0269 (8)	0.0127 (7)	0.0097 (7)	0.0025 (7)
O2	0.0577 (11)	0.0566 (10)	0.0220 (8)	0.0189 (8)	0.0017 (7)	0.0056 (7)
O3	0.0422 (10)	0.0517 (9)	0.0257 (8)	0.0121 (7)	−0.0042 (7)	0.0093 (7)
O4	0.0478 (10)	0.0534 (10)	0.0251 (8)	0.0274 (8)	0.0074 (7)	0.0035 (7)
N1	0.0326 (10)	0.0357 (9)	0.0231 (9)	0.0089 (7)	0.0018 (7)	0.0043 (7)
C1	0.0377 (13)	0.0276 (10)	0.0255 (11)	0.0000 (9)	0.0033 (9)	0.0058 (8)
C2	0.0325 (12)	0.0258 (9)	0.0229 (10)	0.0025 (8)	0.0059 (9)	0.0050 (8)
C3	0.0319 (12)	0.0284 (10)	0.0246 (11)	0.0018 (8)	−0.0012 (9)	0.0081 (8)
C4	0.0282 (11)	0.0322 (10)	0.0323 (12)	0.0097 (8)	0.0035 (9)	0.0086 (9)
C5	0.0327 (12)	0.0271 (10)	0.0271 (11)	0.0052 (8)	0.0059 (9)	0.0062 (8)
C6	0.0289 (11)	0.0242 (9)	0.0205 (10)	0.0036 (8)	0.0000 (8)	0.0038 (8)
C7	0.0272 (11)	0.0251 (9)	0.0261 (11)	0.0037 (8)	0.0049 (8)	0.0047 (8)
O5	0.0415 (9)	0.0386 (8)	0.0343 (8)	0.0153 (7)	0.0085 (7)	0.0085 (7)
O6	0.0468 (10)	0.0400 (8)	0.0408 (9)	0.0073 (7)	0.0065 (8)	0.0045 (7)
Cl1	0.0335 (3)	0.0385 (3)	0.0323 (3)	0.0111 (2)	0.0022 (2)	0.0086 (2)

O1—C1	1.317 (2)	C2—C7	1.397 (3)
O1—H1	0.8200	C2—C3	1.410 (3)
O2—C1	1.225 (2)	C3—C4	1.390 (3)
O3—C3	1.346 (2)	C4—C5	1.376 (3)
O3—H3	0.8199	C4—H4	0.9300
O4—C5	1.358 (2)	C5—C6	1.397 (3)
O4—H4A	0.8200	C6—C7	1.365 (3)
N1—C6	1.470 (2)	C7—H7	0.9300
N1—H1A	0.8900	O5—H5A	0.8616
N1—H1B	0.8900	O5—H5B	0.8517
N1—H1C	0.8900	O6—H6A	0.8764
C1—C2	1.467 (3)	O6—H6B	0.8647
C1—O1—H1	109.5	O3—C3—C2	123.24 (18)
C3—O3—H3	109.5	C4—C3—C2	120.50 (18)
C5—O4—H4A	109.5	C5—C4—C3	119.87 (18)
C6—N1—H1A	109.5	C5—C4—H4	120.1
C6—N1—H1B	109.5	C3—C4—H4	120.1
H1A—N1—H1B	109.5	O4—C5—C4	124.58 (17)
C6—N1—H1C	109.5	O4—C5—C6	115.57 (17)
H1A—N1—H1C	109.5	C4—C5—C6	119.85 (18)
H1B—N1—H1C	109.5	C7—C6—C5	120.75 (18)
O2—C1—O1	122.79 (18)	C7—C6—N1	121.88 (16)
O2—C1—C2	123.65 (19)	C5—C6—N1	117.31 (16)
O1—C1—C2	113.56 (17)	C6—C7—C2	120.62 (17)
C7—C2—C3	118.40 (17)	C6—C7—H7	119.7
C7—C2—C1	120.94 (18)	C2—C7—H7	119.7
C3—C2—C1	120.67 (18)	H5A—O5—H5B	104.7
O3—C3—C4	116.25 (17)	H6A—O6—H6B	106.8

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O6	0.82	1.88	2.6945 (19)	171
O3—H3···O2	0.82	1.96	2.672 (2)	145
O4—H4A···Cl1i	0.82	2.21	3.0097 (15)	164
N1—H1A···O6ii	0.89	2.02	2.903 (2)	169
N1—H1B···O5iii	0.89	1.96	2.853 (2)	178
N1—H1C···Cl1iv	0.89	2.35	3.1950 (18)	157
O5—H5A···O2v	0.86	2.16	2.935 (2)	149
O5—H5B···Cl1	0.85	2.41	3.1494 (15)	146
O6—H6A···Cl1	0.88	2.27	3.1386 (16)	174
O6—H6B···O5vi	0.86	1.99	2.850 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O6	0.82	1.88	2.6945 (19)	171
O3—H3⋯O2	0.82	1.96	2.672 (2)	145
O4—H4A⋯Cl1i	0.82	2.21	3.0097 (15)	164
N1—H1A⋯O6ii	0.89	2.02	2.903 (2)	169
N1—H1B⋯O5iii	0.89	1.96	2.853 (2)	178
N1—H1C⋯Cl1iv	0.89	2.35	3.1950 (18)	157
O5—H5A⋯O2v	0.86	2.16	2.935 (2)	149
O5—H5B⋯Cl1	0.85	2.41	3.1494 (15)	146
O6—H6A⋯Cl1	0.88	2.27	3.1386 (16)	174
O6—H6B⋯O5vi	0.86	1.99	2.850 (2)	173

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .