Hydrogen bonding in 2-carboxy­anilinium dihydrogen phosphite at 100 K

Benali-Cherif, N.; Allouche, F.; Direm, A.; Soudani, K.

doi:10.1107/S1600536809007077

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o664-o665

doi:10.1107/S1600536809007077

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Hydrogen bonding in 2-carboxyanilinium dihydrogen phosphite at 100 K

Nourredine Benali-Cherif,^a ^* Fatima Allouche,^a Amani Direm ^a and Kawther Soudani ^a

^aLaboratoire des Structures, Propriétés et Interactions Inter Atomiques (LASPI²A), Centre Universitaire de Khenchela, 40000 Khenchela, Algeria
^*Correspondence e-mail: benalicherif@hotmail.com

(Received 13 February 2009; accepted 25 February 2009; online 6 March 2009)

The title compound, C₇H₈NO₂⁺·H₂PO₃⁻, is formed from alternating layers of organic cations and inorganic anions stacked along the a-axis direction. They are associated via O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonding, giving rise to two different R₂²(8) graph-set motifs and generating a three-dimensional network.

Related literature

For applications of hybrid compounds, see: Kagan et al. (1999 ); Mazeaud et al. (2000 ); Benali-Cherif, Direm et al. (2007 ). For applications of anthranilic acid derivatives, see: He et al. (2003 ); Per Wiklund et al. (2004 ); Congiu et al. (2005 ); Nittoli et al. (2005 ). For related structured, see: Bendeif et al. (2003 , 2009 ); Benali-Cherif, Allouche et al. (2007 ). For graph-set theory, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₇H₈NO₂⁺·H₂PO₃⁻
M_r = 219.13
Triclinic, $[P \overline 1]$
a = 4.8757 (6) Å
b = 9.4597 (6) Å
c = 10.0801 (5) Å
α = 78.929 (3)°
β = 76.058 (4)°
γ = 86.814 (2)°
V = 442.81 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 100 K
0.25 × 0.18 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur Saphire2 diffractometer
Absorption correction: integration (ABSORB; DeTitta, 1985 ) T_min = 0.972, T_max = 0.985
11058 measured reflections
2581 independent reflections
2559 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.093
S = 1.07
2581 reflections
127 parameters
H-atom parameters not refined
Δρ_max = 0.58 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
O1—H1⋯O3ⁱ	0.84	1.77	2.6085 (13)	178
N1—H1A⋯O4	0.91	1.96	2.8589 (14)	169
N1—H1B⋯O4ⁱⁱ	0.91	2.02	2.9160 (13)	169
N1—H1C⋯O4ⁱⁱⁱ	0.91	1.97	2.8740 (14)	173
O5—H5O⋯O3^iv	0.84	1.78	2.6059 (13)	167
C6—H6⋯O5^v	0.95	2.55	3.2542 (15)	132
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y+1, -z; (iii) x+1, y, z; (iv) -x, -y+2, -z; (v) -x, -y+1, -z+1.

Data collection: KappaCCD Server Software (Nonius, 1998 ); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007077/bg2238sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007077/bg2238Isup2.hkl

checkCIF report

Comment top

The crystal structures of organic-inorganic hybrid materials have been extensively investigated due to their interest in the field of new materials, and the number of reported structures is rapidly growing owing to their applications in medicine, material science and to their electrical, magnetic and optical properties (Kagan et al., 1999; Mazeaud et al., 2000) and the hydrogen bonding richness of these structures. This kind of hydrogen bonding appears in the active sites of several biological systems and is observed in similar previously studied hybrid compounds (Benali-Cherif, Direm et al., 2007).

As well as being a biochemical precursor of the amino acids tryptophan, phenylalanine and tyrosine, anthranilic acid is used as a useful derivating agent for carbohydrate analysis (He et al., 2003). 2-Aminobenzoic acid is present as a part of the core structure of certain alkaloids, synthetic drugs (Per Wiklund et al., 2004), antiinflammatory, anticancer agents (Congiu et al., 2005) and as inhibitor of Hepatitis C NS5B polymerase (Nittoli et al., 2005).

The title compound structure (I) is composed of cationic HOO-C₆H₄—NH₃⁺ and anionic (H₂PO₃^-) groups (Fig.1). All bond lengths and angles of the (H₂PO₃^-) tetrahedra and the o-carboxyanilinium cations are within normal ranges, in a good agreement with those observed in the litterature (Bendeif et al. 2003, Bendeif et al. 2009) and (Benali-Cherif, Allouche et al., 2007), respectively.

The three H atoms of the anilinium group are subsequently involved in extensive N—H···O hydrogen-bonding (Table 1) interactions with O4 being a multiple acceptor of three different phosphite anions, while O3 behaves as double acceptor of hydrogen bonds from one cation, via O1 in the carboxylic group, and one anion, via O5 in the phosphite anion. These interactions give raise to two different R₂²(8) graph set motifs (Bernstein et al. 1995), shown in Fig. 2. In addition, there are intramolecular interactions involving the benzene ring and the carboxylic group ensuring cohesion and stability of the crystal structiure.

Related literature top

For hybrid compound applications, see: Kagan et al. (1999); Mazeaud et al. (2000); Benali-Cherif, Direm et al. (2007). For applications of anthranilic acid derivatives, see: He et al. (2003). Per Wiklund et al. (2004); Congiu et al. (2005); Nittoli et al. (2005). For related structured, see: Bendeif et al. (2003, 2009); Benali-Cherif, Allouche et al. (2007). For graph-set theory, see: Bernstein et al. (1995).

Experimental top

Crystals of anthranilicium phosphite are prepared by slow evaporation at room temperature of an aqueous solution of 2-aminobenzoic acid and H₃PO₃ in a 1:1 stochiometric ratio.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of the asymmetric unit of C₇H₈NO₂⁺.H₂PO₃^- showing atom labels and suggesting the hydrogen bondings richness. Displacement factors drawn at a 50% level.
	Fig. 2. Unit cell projection down a, showing the two different R₂²(8) graph motifs in the structure.

2-carboxyanilinium dihydrogen phosphite top

Crystal data top

C₇H₈NO₂⁺·H₂PO₃⁻	Z = 2
M_r = 219.13	F(000) = 228
Triclinic, P1	D_x = 1.643 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.8757 (6) Å	Cell parameters from 11058 reflections
b = 9.4597 (6) Å	θ = 2.8–32.7°
c = 10.0801 (5) Å	µ = 0.31 mm⁻¹
α = 78.929 (3)°	T = 100 K
β = 76.058 (4)°	Prism, colourless
γ = 86.814 (2)°	0.25 × 0.18 × 0.05 mm
V = 442.81 (7) Å³

Data collection top

Oxford Diffraction Xcalibur Saphire2 diffractometer	2581 independent reflections
Radiation source: fine-focus sealed tube	2559 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 8.4221 pixels mm^-1	θ_max = 30.0°, θ_min = 2.8°
ω and θ scans	h = −6→6
Absorption correction: integration (ABSORB; DeTitta, 1985)	k = −12→13
T_min = 0.972, T_max = 0.985	l = 0→14
11058 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)] = 0.033	Hydrogen site location: difference Fourier map
wR(F²) = 0.093	H-atom parameters not refined
S = 1.07	w = 1/[σ²(F_o²) + (0.0537P)² + 0.2002P] where P = (F_o² + 2F_c²)/3
2581 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₇H₈NO₂⁺·H₂PO₃⁻	γ = 86.814 (2)°
M_r = 219.13	V = 442.81 (7) Å³
Triclinic, P1	Z = 2
a = 4.8757 (6) Å	Mo Kα radiation
b = 9.4597 (6) Å	µ = 0.31 mm⁻¹
c = 10.0801 (5) Å	T = 100 K
α = 78.929 (3)°	0.25 × 0.18 × 0.05 mm
β = 76.058 (4)°

Data collection top

Oxford Diffraction Xcalibur Saphire2 diffractometer	2581 independent reflections
Absorption correction: integration (ABSORB; DeTitta, 1985)	2559 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.985	R_int = 0.035
11058 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.093	H-atom parameters not refined
S = 1.07	Δρ_max = 0.58 e Å⁻³
2581 reflections	Δρ_min = −0.24 e Å⁻³
127 parameters

Special details top

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

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

	x	y	z	U_iso*/U_eq
O1	1.22190 (19)	0.11913 (10)	0.23669 (10)	0.01503 (19)
H1	1.3765	0.1163	0.1783	0.023*
O2	1.18445 (19)	0.33344 (10)	0.10200 (9)	0.01319 (18)
N1	0.6956 (2)	0.48161 (11)	0.14593 (10)	0.0107 (2)
H1A	0.5423	0.5400	0.1407	0.013*
H1B	0.7309	0.4308	0.0754	0.013*
H1C	0.8484	0.5361	0.1386	0.013*
C1	1.0902 (2)	0.24260 (13)	0.20403 (12)	0.0109 (2)
C2	0.8201 (2)	0.26393 (13)	0.30600 (12)	0.0106 (2)
C3	0.6396 (3)	0.38167 (13)	0.27952 (12)	0.0104 (2)
C4	0.3987 (3)	0.40572 (13)	0.37899 (13)	0.0131 (2)
H4	0.2794	0.4862	0.3601	0.016*
C5	0.3322 (3)	0.31144 (14)	0.50686 (13)	0.0150 (2)
H5	0.1688	0.3284	0.5755	0.018*
C6	0.5051 (3)	0.19272 (15)	0.53363 (13)	0.0157 (2)
H6	0.4584	0.1276	0.6199	0.019*
C7	0.7466 (3)	0.16969 (14)	0.43364 (13)	0.0141 (2)
H7	0.8639	0.0883	0.4525	0.017*
P1	0.19035 (6)	0.80587 (3)	0.08601 (3)	0.01016 (10)
O3	0.29056 (19)	0.88933 (10)	−0.06075 (9)	0.01379 (18)
O4	0.20062 (18)	0.64347 (9)	0.10464 (9)	0.01255 (18)
O5	−0.1212 (2)	0.85119 (10)	0.14917 (10)	0.0166 (2)
H5O	−0.1511	0.9363	0.1122	0.025*
H	0.3396	0.8447	0.1629	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0120 (4)	0.0112 (4)	0.0180 (4)	0.0041 (3)	−0.0003 (3)	0.0013 (3)
O2	0.0124 (4)	0.0120 (4)	0.0132 (4)	0.0011 (3)	−0.0016 (3)	0.0003 (3)
N1	0.0102 (5)	0.0093 (4)	0.0118 (5)	0.0016 (3)	−0.0022 (3)	−0.0011 (3)
C1	0.0102 (5)	0.0099 (5)	0.0131 (5)	0.0011 (4)	−0.0039 (4)	−0.0025 (4)
C2	0.0097 (5)	0.0101 (5)	0.0118 (5)	0.0003 (4)	−0.0030 (4)	−0.0013 (4)
C3	0.0117 (5)	0.0093 (5)	0.0101 (5)	−0.0004 (4)	−0.0031 (4)	−0.0013 (4)
C4	0.0122 (5)	0.0128 (5)	0.0141 (5)	0.0013 (4)	−0.0020 (4)	−0.0036 (4)
C5	0.0134 (5)	0.0180 (6)	0.0128 (5)	−0.0004 (4)	−0.0006 (4)	−0.0042 (4)
C6	0.0172 (6)	0.0175 (6)	0.0103 (5)	−0.0013 (5)	−0.0016 (4)	0.0014 (4)
C7	0.0137 (5)	0.0130 (6)	0.0142 (5)	0.0016 (4)	−0.0036 (4)	0.0008 (4)
P1	0.01028 (15)	0.00778 (15)	0.01211 (15)	0.00126 (10)	−0.00279 (11)	−0.00126 (10)
O3	0.0124 (4)	0.0106 (4)	0.0148 (4)	0.0029 (3)	0.0006 (3)	0.0007 (3)
O4	0.0124 (4)	0.0082 (4)	0.0166 (4)	0.0013 (3)	−0.0040 (3)	−0.0009 (3)
O5	0.0149 (4)	0.0110 (4)	0.0181 (4)	0.0053 (3)	0.0026 (3)	0.0018 (3)

Geometric parameters (Å, º) top

O1—C1	1.3250 (14)	C4—H4	0.9500
O1—H1	0.8399	C5—C6	1.3902 (18)
O2—C1	1.2182 (15)	C5—H5	0.9500
N1—C3	1.4643 (15)	C6—C7	1.3908 (17)
N1—H1A	0.9100	C6—H6	0.9500
N1—H1B	0.9100	C7—H7	0.9500
N1—H1C	0.9101	P1—O4	1.5110 (9)
C1—C2	1.4930 (16)	P1—O3	1.5154 (9)
C2—C7	1.3970 (16)	P1—O5	1.5695 (9)
C2—C3	1.4060 (16)	P1—H	1.2947
C3—C4	1.3880 (16)	O5—H5O	0.8400
C4—C5	1.3969 (17)

C1—O1—H1	109.5	C5—C4—H4	120.1
C3—N1—H1A	109.5	C6—C5—C4	120.00 (11)
C3—N1—H1B	109.5	C6—C5—H5	120.0
H1A—N1—H1B	109.5	C4—C5—H5	120.0
C3—N1—H1C	109.5	C5—C6—C7	119.76 (12)
H1A—N1—H1C	109.5	C5—C6—H6	120.1
H1B—N1—H1C	109.5	C7—C6—H6	120.1
O2—C1—O1	123.21 (11)	C6—C7—C2	121.25 (12)
O2—C1—C2	122.48 (11)	C6—C7—H7	119.4
O1—C1—C2	114.27 (10)	C2—C7—H7	119.4
C7—C2—C3	118.21 (11)	O4—P1—O3	116.92 (5)
C7—C2—C1	120.31 (11)	O4—P1—O5	107.62 (5)
C3—C2—C1	121.42 (11)	O3—P1—O5	109.90 (5)
C4—C3—C2	120.87 (11)	O4—P1—H	108.37
C4—C3—N1	117.68 (10)	O3—P1—H	108.24
C2—C3—N1	121.44 (10)	O5—P1—H	105.16
C3—C4—C5	119.89 (11)	P1—O5—H5O	109.5
C3—C4—H4	120.1

O2—C1—C2—C7	−168.18 (12)	C2—C3—C4—C5	−0.57 (19)
O1—C1—C2—C7	9.66 (16)	N1—C3—C4—C5	178.45 (11)
O2—C1—C2—C3	9.07 (18)	C3—C4—C5—C6	−0.83 (19)
O1—C1—C2—C3	−173.09 (11)	C4—C5—C6—C7	1.1 (2)
C7—C2—C3—C4	1.67 (18)	C5—C6—C7—C2	0.1 (2)
C1—C2—C3—C4	−175.63 (11)	C3—C2—C7—C6	−1.42 (18)
C7—C2—C3—N1	−177.31 (11)	C1—C2—C7—C6	175.92 (12)
C1—C2—C3—N1	5.39 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱ	0.84	1.77	2.6085 (13)	178
N1—H1A···O4	0.91	1.96	2.8589 (14)	169
N1—H1B···O4ⁱⁱ	0.91	2.02	2.9160 (13)	169
N1—H1C···O4ⁱⁱⁱ	0.91	1.97	2.8740 (14)	173
O5—H5O···O3^iv	0.84	1.78	2.6059 (13)	167
C6—H6···O5^v	0.95	2.55	3.2542 (15)	132
C7—H7···O1	0.95	2.42	2.7503 (16)	101

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

Experimental details

Crystal data
Chemical formula	C₇H₈NO₂⁺·H₂PO₃⁻
M_r	219.13
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	4.8757 (6), 9.4597 (6), 10.0801 (5)
α, β, γ (°)	78.929 (3), 76.058 (4), 86.814 (2)
V (Å³)	442.81 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.25 × 0.18 × 0.05

Data collection
Diffractometer	Oxford Diffraction Xcalibur Saphire2 diffractometer
Absorption correction	Integration (ABSORB; DeTitta, 1985)
T_min, T_max	0.972, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	11058, 2581, 2559
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.093, 1.07
No. of reflections	2581
No. of parameters	127
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.24

Computer programs: KappaCCD Server Software (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱ	0.84	1.77	2.6085 (13)	178
N1—H1A···O4	0.91	1.96	2.8589 (14)	169
N1—H1B···O4ⁱⁱ	0.91	2.02	2.9160 (13)	169
N1—H1C···O4ⁱⁱⁱ	0.91	1.97	2.8740 (14)	173
O5—H5O···O3^iv	0.84	1.78	2.6059 (13)	167
C6—H6···O5^v	0.95	2.55	3.2542 (15)	132
C7—H7···O1	0.95	2.42	2.7503 (16)	101

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

Acknowledgements

We wish to thank Dr C. Lecomte of LCM3B (UMR UHP –CNRS 7036), Faculté des Sciences et Techniques 54506 Vandoeuvre-lès-Nancy CEDEX, for providing diffraction facilities in his laboratory, and le Centre Universitaire de Khenchela for financial support.

References

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