3-Ammonio-4-hydroxy­benzoate monohydrate

Ullah, S.; Tahir, M.N.; Shahwar, D.; Khan, Z.-D.; Khan, M.A.

doi:10.1107/S1600536809017462

organic compounds

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Volume 65| Part 6| June 2009| Page o1304

doi:10.1107/S1600536809017462

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3-Ammonio-4-hydroxybenzoate monohydrate

Sami Ullah,^a M. Nawaz Tahir,^b ^* Durre Shahwar,^a Zaheer-ud-Din Khan ^c and Muhammad Akmal Khan ^a

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cDepartment of Botany, Government College University, Lahore, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 7 May 2009; accepted 9 May 2009; online 14 May 2009)

The title compound, C₇H₇NO₃·H₂O, which crystallized as a hydrate, was obtained from an extraction of the plant species Saussurea atkinsonii of the asteraceae family collected from the hilly area (Ayubia) of Pakistan during the flowering season. The dihedral angle between the benzene ring and the carboxylate group is 25.64 (5)°. In the crystal, the packing is consolidated by N—H⋯O and O—H⋯O hydrogen bonds, as well as weak aromatic π–π stacking [centroid–centroid separation = 3.9365 (9) Å] and C=O⋯π interactions.

Related literature

For a related structure, see: Bertasso et al. (2001 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₇H₇NO₃·H₂O
M_r = 171.15
Orthorhombic, P b c a
a = 8.7711 (3) Å
b = 12.7193 (7) Å
c = 12.9289 (6) Å
V = 1442.38 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 296 K
0.26 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.971, T_max = 0.976
8827 measured reflections
1725 independent reflections
1277 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.118
S = 1.06
1725 reflections
127 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.952 (18)	1.945 (18)	2.8884 (16)	170.4 (14)
N1—H1A⋯O2ⁱ	0.952 (18)	2.335 (18)	2.9008 (18)	117.6 (13)
N1—H1B⋯O4ⁱⁱ	0.944 (19)	2.001 (19)	2.8957 (19)	157.4 (16)
N1—H1C⋯O1ⁱⁱⁱ	0.933 (17)	1.860 (17)	2.7846 (18)	170.5 (16)
O3—H3⋯O4^iv	0.904 (18)	1.760 (18)	2.6456 (15)	166.0 (19)
O4—H41⋯O2^iv	0.90 (2)	1.80 (2)	2.6945 (18)	171.1 (17)
O4—H42⋯O1ⁱⁱⁱ	0.884 (19)	2.03 (2)	2.9027 (18)	168.8 (17)
C6—H6⋯O3^v	0.93	2.55	3.446 (2)	161
C7—O2⋯CgA^vi	1.25 (1)	3.49 (1)	3.9313 (16)	101 (1)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (v) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (vi) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017462/hb2969sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017462/hb2969Isup2.hkl

checkCIF report

Comment top

The medicinal plants are available all over the world. Locally available plant specie Saussurea atkinsonii of asteraceae family was collected from hilly area (Ayubia) of Pakistan during the flowering season. The plant was dried inside room for 20–25 days. The title compound (I), (Fig. 1), is an extract of it in chloroform and methanol. The study of its bio-activity is in progress.

The crystal structure of (II) (4-vinylphenyl 3-amino-4-hydroxybenzoate or bagremycin A (Bertasso et al., 2001), has been reported which contains the aromatic ring along with heavy atoms of the substituants of (I). In the title compound, the bond distances and bond angles are within normal ranges (Allen et al., 1987). The benzene ring A (C1–C6) is planar and is oriented at a dihedral angle of 25.64 (5)° with the CO₂ group. The N-atom of ammonium is in plane of the ring A, whereas the O-atom of hydroxy group is at a distance of -0.0580 (21) Å from the same.

There exist intensive intermolecular H-bonding (Table 1), resulting in three-dimensional polymeric network. There also exist CgA···CgAⁱ [symmetry code i = 1 - x, 1 - y, -z] interaction at a distance of 3.9365 (9) Å, where CgA is the centroid of aromatic ring. The molecules may also be stabilized due to C==O···π interaction (Table 1).

Related literature top

For a related structure, see: Bertasso et al. (2001). For reference structural data, see: Allen et al. (1987).

Experimental top

The Specie Saussurea atkinsonii of asteraceae family was dried inside room for 20–25 days as a whole and grinded. The extract was obtained using soxhlet apparatus in 50% chloroform and 50% methanol and it was subjected to isolation by performing column chromatography and thin layer chromatography. The extract obtained was recrystallized from methanol and light brown rods of (I) were obtained. The water found in the structure was presumably incorporated from the atomsphere.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Spek, 2009).

Figures top

	Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radius.
	Fig. 2. The partial packing of (I), showing that molecules form three-dimensional polymeric network.

3-Ammonio-4-hydroxybenzoate monohydrate top

Crystal data top

C₇H₇NO₃·H₂O	F(000) = 720
M_r = 171.15	D_x = 1.576 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1725 reflections
a = 8.7711 (3) Å	θ = 3.2–28.3°
b = 12.7193 (7) Å	µ = 0.13 mm⁻¹
c = 12.9289 (6) Å	T = 296 K
V = 1442.38 (11) Å³	Rod, light brown
Z = 8	0.26 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	1752 independent reflections
Radiation source: fine-focus sealed tube	1277 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.3°, θ_min = 3.2°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→16
T_min = 0.971, T_max = 0.976	l = −11→17
8827 measured reflections

Refinement top

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0684P)² + 0.0409P] where P = (F_o² + 2F_c²)/3
1725 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₇H₇NO₃·H₂O	V = 1442.38 (11) Å³
M_r = 171.15	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.7711 (3) Å	µ = 0.13 mm⁻¹
b = 12.7193 (7) Å	T = 296 K
c = 12.9289 (6) Å	0.26 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	1752 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1277 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.976	R_int = 0.033
8827 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.31 e Å⁻³
1725 reflections	Δρ_min = −0.24 e Å⁻³
127 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.69598 (12)	0.67023 (9)	0.16442 (9)	0.0284 (4)
O2	0.83764 (11)	0.53206 (10)	0.12269 (9)	0.0302 (4)
O3	0.20823 (11)	0.29862 (10)	0.11448 (10)	0.0319 (4)
N1	0.48231 (14)	0.21872 (11)	0.16388 (11)	0.0232 (4)
C1	0.57236 (15)	0.50443 (12)	0.14203 (11)	0.0205 (5)
C2	0.58869 (15)	0.39732 (13)	0.15731 (11)	0.0203 (4)
C3	0.46511 (14)	0.33137 (12)	0.14912 (11)	0.0193 (4)
C4	0.32078 (15)	0.37051 (12)	0.12444 (12)	0.0212 (4)
C5	0.30300 (15)	0.47766 (13)	0.11230 (12)	0.0241 (5)
C6	0.42742 (15)	0.54444 (13)	0.12153 (12)	0.0232 (4)
C7	0.71208 (15)	0.57284 (13)	0.14299 (11)	0.0216 (5)
O4	0.43081 (12)	0.34489 (11)	0.45169 (10)	0.0308 (4)
H1A	0.587 (2)	0.2008 (14)	0.1721 (12)	0.0278*
H1B	0.4519 (19)	0.1828 (14)	0.1034 (15)	0.0278*
H1C	0.4229 (18)	0.1948 (14)	0.2189 (14)	0.0278*
H2	0.68403	0.36974	0.17325	0.0243*
H3	0.119 (2)	0.3252 (16)	0.0913 (15)	0.0383*
H5	0.20714	0.50524	0.09785	0.0289*
H6	0.41402	0.61656	0.11398	0.0279*
H41	0.3898 (19)	0.4057 (16)	0.4289 (15)	0.0369*
H42	0.381 (2)	0.2927 (16)	0.4217 (15)	0.0369*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0316 (5)	0.0154 (7)	0.0383 (7)	−0.0051 (4)	0.0053 (4)	−0.0044 (5)
O2	0.0231 (5)	0.0245 (7)	0.0430 (7)	−0.0032 (5)	0.0043 (4)	−0.0063 (5)
O3	0.0193 (5)	0.0217 (7)	0.0548 (8)	−0.0032 (4)	−0.0059 (5)	0.0000 (6)
N1	0.0214 (6)	0.0150 (8)	0.0331 (8)	0.0010 (5)	0.0027 (5)	0.0015 (6)
C1	0.0236 (7)	0.0164 (9)	0.0216 (8)	−0.0029 (5)	0.0013 (5)	−0.0026 (6)
C2	0.0183 (6)	0.0190 (9)	0.0235 (8)	0.0006 (5)	0.0011 (5)	−0.0006 (6)
C3	0.0209 (6)	0.0142 (9)	0.0228 (8)	0.0003 (5)	0.0018 (5)	0.0013 (6)
C4	0.0195 (6)	0.0188 (9)	0.0254 (8)	−0.0024 (5)	−0.0004 (5)	−0.0019 (6)
C5	0.0205 (6)	0.0218 (9)	0.0300 (9)	0.0041 (6)	−0.0024 (6)	0.0003 (7)
C6	0.0290 (7)	0.0137 (8)	0.0270 (8)	0.0014 (6)	0.0000 (5)	0.0005 (7)
C7	0.0265 (7)	0.0169 (9)	0.0214 (8)	−0.0044 (6)	0.0013 (5)	−0.0002 (6)
O4	0.0257 (5)	0.0255 (8)	0.0412 (7)	0.0017 (5)	−0.0044 (4)	0.0023 (6)

Geometric parameters (Å, º) top

O1—C7	1.277 (2)	C1—C7	1.503 (2)
O2—C7	1.2453 (17)	C1—C6	1.3948 (19)
O3—C4	1.3518 (18)	C1—C2	1.384 (2)
O3—H3	0.904 (18)	C2—C3	1.375 (2)
O4—H41	0.90 (2)	C3—C4	1.3972 (19)
O4—H42	0.884 (19)	C4—C5	1.381 (2)
N1—C3	1.453 (2)	C5—C6	1.388 (2)
N1—H1C	0.933 (17)	C2—H2	0.9300
N1—H1A	0.952 (18)	C5—H5	0.9300
N1—H1B	0.944 (19)	C6—H6	0.9300

C4—O3—H3	114.3 (13)	O3—C4—C5	125.06 (12)
H41—O4—H42	107.7 (17)	C3—C4—C5	118.69 (13)
C3—N1—H1A	110.5 (11)	O3—C4—C3	116.26 (13)
C3—N1—H1B	109.8 (11)	C4—C5—C6	120.36 (13)
H1A—N1—H1B	104.4 (14)	C1—C6—C5	120.64 (15)
H1A—N1—H1C	112.1 (14)	O1—C7—O2	123.20 (14)
C3—N1—H1C	111.3 (11)	O2—C7—C1	118.57 (14)
H1B—N1—H1C	108.4 (15)	O1—C7—C1	118.24 (12)
C2—C1—C6	118.72 (13)	C3—C2—H2	120.00
C2—C1—C7	118.97 (12)	C1—C2—H2	120.00
C6—C1—C7	122.24 (14)	C4—C5—H5	120.00
C1—C2—C3	120.53 (13)	C6—C5—H5	120.00
N1—C3—C2	120.64 (12)	C1—C6—H6	120.00
C2—C3—C4	120.97 (14)	C5—C6—H6	120.00
N1—C3—C4	118.38 (12)

C6—C1—C2—C3	2.1 (2)	C1—C2—C3—C4	0.5 (2)
C7—C1—C2—C3	−175.02 (13)	N1—C3—C4—O3	−1.1 (2)
C2—C1—C6—C5	−2.7 (2)	N1—C3—C4—C5	178.75 (14)
C7—C1—C6—C5	174.30 (14)	C2—C3—C4—O3	177.60 (14)
C2—C1—C7—O1	−156.35 (14)	C2—C3—C4—C5	−2.5 (2)
C2—C1—C7—O2	23.8 (2)	O3—C4—C5—C6	−178.25 (15)
C6—C1—C7—O1	26.7 (2)	C3—C4—C5—C6	1.9 (2)
C6—C1—C7—O2	−153.17 (15)	C4—C5—C6—C1	0.7 (2)
C1—C2—C3—N1	179.24 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.952 (18)	1.945 (18)	2.8884 (16)	170.4 (14)
N1—H1A···O2ⁱ	0.952 (18)	2.335 (18)	2.9008 (18)	117.6 (13)
N1—H1B···O4ⁱⁱ	0.944 (19)	2.001 (19)	2.8957 (19)	157.4 (16)
N1—H1C···O1ⁱⁱⁱ	0.933 (17)	1.860 (17)	2.7846 (18)	170.5 (16)
O3—H3···O4^iv	0.904 (18)	1.760 (18)	2.6456 (15)	166.0 (19)
O4—H41···O2^iv	0.90 (2)	1.80 (2)	2.6945 (18)	171.1 (17)
O4—H42···O1ⁱⁱⁱ	0.884 (19)	2.03 (2)	2.9027 (18)	168.8 (17)
C6—H6···O3^v	0.93	2.55	3.446 (2)	161
C7—O2···CgA^vi	1.25 (1)	3.49 (1)	3.9313 (16)	101 (1)

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) x, −y+1/2, z−1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) x−1/2, y, −z+1/2; (v) −x+1/2, y+1/2, z; (vi) x+1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₇H₇NO₃·H₂O
M_r	171.15
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	8.7711 (3), 12.7193 (7), 12.9289 (6)
V (Å³)	1442.38 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.26 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.971, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	8827, 1752, 1277
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.118, 1.06
No. of reflections	1725
No. of parameters	127
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.952 (18)	1.945 (18)	2.8884 (16)	170.4 (14)
N1—H1A···O2ⁱ	0.952 (18)	2.335 (18)	2.9008 (18)	117.6 (13)
N1—H1B···O4ⁱⁱ	0.944 (19)	2.001 (19)	2.8957 (19)	157.4 (16)
N1—H1C···O1ⁱⁱⁱ	0.933 (17)	1.860 (17)	2.7846 (18)	170.5 (16)
O3—H3···O4^iv	0.904 (18)	1.760 (18)	2.6456 (15)	166.0 (19)
O4—H41···O2^iv	0.90 (2)	1.80 (2)	2.6945 (18)	171.1 (17)
O4—H42···O1ⁱⁱⁱ	0.884 (19)	2.03 (2)	2.9027 (18)	168.8 (17)
C6—H6···O3^v	0.93	2.55	3.446 (2)	161
C7—O2···CgA^vi	1.2453 (17)	3.4940 (13)	3.9313 (16)	101.24 (9)

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) x, −y+1/2, z−1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) x−1/2, y, −z+1/2; (v) −x+1/2, y+1/2, z; (vi) x+1/2, y, −z+1/2.

Acknowledgements

SU greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing a Scholarship under the Indigenous PhD Program (PIN 042–121314-PS2–287).

References

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