2-(Methoxy-carbon-yl)anilinium dihydrogen phosphate.

The title compound, C(8)H(10)NO(2) (+)·H(2)PO(4) (-), is a derivative of the naturally occurring compound methyl-anthranilate. The asymmetric unit comprises the 2-(methoxy-carbon-yl)anilinium cation and the dihydrogen phosphate anion. In the cation, the dihedral angle between the benzene ring plane and that through the methyl ester substituent is 22.94 (9)°. In the crystal, adjacent cations and anions form dimers through N-H⋯O and O-H⋯O hydrogen bonds, respectively. Additional N-H⋯O and C-H⋯O contacts result in a network of cation and anion dimers stacked down the b axis.

Related literature

For thia­zine-related heterocycles see: Shafiq et al. (2009a ▶). For related structures, see: Gel’mbol’dt et al. (2006 ▶); Ma et al. (2005 ▶); Shafiq et al. (2008 ▶, 2009b ▶).

Experimental

Crystal data

C8H10NO2 +·H2PO4 −

M = 249.16

Monoclinic,

a = 20.939 (3) Å

b = 4.7880 (5) Å

c = 22.283 (4) Å

β = 114.970 (5)°

V = 2025.2 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.39 × 0.21 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.928, T max = 0.958

10812 measured reflections

2413 independent reflections

2078 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.07

2413 reflections

153 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.48 e Å−3

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: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025252/bt2987sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025252/bt2987Isup2.hkl

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

C8H10NO2+·H2PO4−	F(000) = 1040
Mr = 249.16	Dx = 1.634 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5124 reflections
a = 20.939 (3) Å	θ = 2.2–27.9°
b = 4.7880 (5) Å	µ = 0.29 mm−1
c = 22.283 (4) Å	T = 296 K
β = 114.970 (5)°	Needle, colourless
V = 2025.2 (5) Å3	0.39 × 0.21 × 0.17 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	2413 independent reflections
Radiation source: fine-focus sealed tube	2078 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 27.9°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −27→27
Tmin = 0.928, Tmax = 0.958	k = −4→6
10812 measured reflections	l = −29→27

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0575P)2 + 1.6713P] where P = (Fo2 + 2Fc2)/3
2413 reflections	(Δ/σ)max = 0.001
153 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.24287 (7)	0.4968 (3)	0.93401 (6)	0.0200 (3)
H1A	0.2695	0.3443	0.9473	0.030*
H1B	0.2127	0.5014	0.9526	0.030*
H1C	0.2702	0.6478	0.9460	0.030*
C1	0.20379 (8)	0.4920 (3)	0.86203 (7)	0.0202 (3)
C2	0.14685 (8)	0.3118 (3)	0.83134 (7)	0.0227 (3)
C3	0.11163 (9)	0.3157 (4)	0.76239 (8)	0.0300 (4)
H3	0.0730	0.1996	0.7412	0.036*
C4	0.13337 (10)	0.4893 (4)	0.72527 (9)	0.0326 (4)
H4	0.1102	0.4864	0.6793	0.039*
C5	0.18948 (10)	0.6671 (4)	0.75648 (9)	0.0322 (4)
H5	0.2038	0.7857	0.7315	0.039*
C6	0.22462 (9)	0.6700 (4)	0.82496 (8)	0.0273 (4)
H6	0.2622	0.7916	0.8459	0.033*
C7	0.12565 (8)	0.1075 (3)	0.86989 (8)	0.0225 (3)
C8	0.03453 (11)	−0.1887 (5)	0.86660 (11)	0.0433 (5)
H8A	0.0609	−0.1795	0.9138	0.065*
H8B	0.0402	−0.3700	0.8511	0.065*
H8C	−0.0144	−0.1566	0.8555	0.065*
O1	0.16391 (6)	0.0261 (3)	0.92428 (6)	0.0273 (3)
O2	0.05989 (7)	0.0218 (3)	0.83567 (7)	0.0380 (3)
P1	0.10739 (2)	0.56312 (8)	0.531833 (19)	0.01826 (13)
O3	0.17510 (6)	0.5066 (2)	0.52576 (6)	0.0248 (3)
O4	0.05239 (6)	0.6781 (3)	0.46425 (6)	0.0262 (3)
H4O	0.0163 (12)	0.681 (5)	0.4598 (10)	0.031*
O5	0.12078 (7)	0.8011 (3)	0.58427 (6)	0.0323 (3)
H5O	0.1063 (13)	0.948 (5)	0.5709 (11)	0.039*
O6	0.07879 (6)	0.3146 (2)	0.55400 (6)	0.0255 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0199 (6)	0.0202 (6)	0.0191 (6)	−0.0008 (5)	0.0075 (5)	−0.0015 (5)
C1	0.0202 (7)	0.0201 (7)	0.0196 (7)	0.0040 (6)	0.0076 (6)	−0.0003 (6)
C2	0.0230 (8)	0.0219 (7)	0.0215 (7)	0.0022 (6)	0.0079 (6)	0.0005 (6)
C3	0.0277 (9)	0.0334 (9)	0.0222 (8)	−0.0011 (7)	0.0038 (6)	−0.0010 (7)
C4	0.0353 (10)	0.0407 (10)	0.0194 (8)	0.0074 (8)	0.0091 (7)	0.0046 (7)
C5	0.0365 (10)	0.0354 (9)	0.0294 (9)	0.0048 (8)	0.0185 (7)	0.0085 (8)
C6	0.0277 (8)	0.0260 (8)	0.0295 (8)	−0.0016 (7)	0.0134 (7)	0.0009 (7)
C7	0.0219 (7)	0.0202 (7)	0.0235 (8)	−0.0008 (6)	0.0077 (6)	−0.0031 (6)
C8	0.0388 (11)	0.0397 (11)	0.0495 (12)	−0.0184 (9)	0.0167 (9)	0.0013 (9)
O1	0.0257 (6)	0.0293 (6)	0.0241 (6)	0.0007 (5)	0.0078 (5)	0.0036 (5)
O2	0.0268 (7)	0.0436 (8)	0.0329 (7)	−0.0137 (6)	0.0022 (5)	0.0073 (6)
P1	0.0173 (2)	0.0154 (2)	0.0226 (2)	0.00185 (14)	0.00890 (16)	0.00206 (14)
O3	0.0181 (6)	0.0250 (6)	0.0324 (6)	0.0032 (4)	0.0118 (5)	0.0025 (5)
O4	0.0179 (5)	0.0338 (7)	0.0261 (6)	0.0029 (5)	0.0086 (5)	0.0069 (5)
O5	0.0466 (8)	0.0189 (6)	0.0277 (6)	0.0072 (5)	0.0122 (6)	0.0001 (5)
O6	0.0234 (6)	0.0186 (5)	0.0363 (6)	0.0010 (4)	0.0142 (5)	0.0060 (5)

N1—C1	1.4609 (19)	C6—H6	0.9300
N1—H1A	0.8900	C7—O1	1.2010 (19)
N1—H1B	0.8900	C7—O2	1.326 (2)
N1—H1C	0.8900	C8—O2	1.443 (2)
C1—C6	1.379 (2)	C8—H8A	0.9600
C1—C2	1.395 (2)	C8—H8B	0.9600
C2—C3	1.396 (2)	C8—H8C	0.9600
C2—C7	1.488 (2)	P1—O3	1.5045 (12)
C3—C4	1.379 (3)	P1—O6	1.5062 (12)
C3—H3	0.9300	P1—O4	1.5597 (12)
C4—C5	1.378 (3)	P1—O5	1.5702 (13)
C4—H4	0.9300	O4—H4O	0.72 (2)
C5—C6	1.386 (2)	O5—H5O	0.78 (2)
C5—H5	0.9300
C1—N1—H1A	109.5	C1—C6—C5	119.85 (16)
C1—N1—H1B	109.5	C1—C6—H6	120.1
H1A—N1—H1B	109.5	C5—C6—H6	120.1
C1—N1—H1C	109.5	O1—C7—O2	124.62 (16)
H1A—N1—H1C	109.5	O1—C7—C2	124.15 (15)
H1B—N1—H1C	109.5	O2—C7—C2	111.21 (14)
C6—C1—C2	120.64 (15)	O2—C8—H8A	109.5
C6—C1—N1	118.39 (14)	O2—C8—H8B	109.5
C2—C1—N1	120.97 (14)	H8A—C8—H8B	109.5
C1—C2—C3	118.45 (15)	O2—C8—H8C	109.5
C1—C2—C7	121.69 (14)	H8A—C8—H8C	109.5
C3—C2—C7	119.77 (15)	H8B—C8—H8C	109.5
C4—C3—C2	120.91 (17)	C7—O2—C8	116.33 (15)
C4—C3—H3	119.5	O3—P1—O6	114.06 (7)
C2—C3—H3	119.5	O3—P1—O4	108.44 (7)
C5—C4—C3	119.79 (16)	O6—P1—O4	111.21 (7)
C5—C4—H4	120.1	O3—P1—O5	108.56 (7)
C3—C4—H4	120.1	O6—P1—O5	107.47 (7)
C4—C5—C6	120.33 (17)	O4—P1—O5	106.83 (7)
C4—C5—H5	119.8	P1—O4—H4O	116.4 (17)
C6—C5—H5	119.8	P1—O5—H5O	117.1 (18)
C6—C1—C2—C3	0.1 (2)	N1—C1—C6—C5	178.83 (15)
N1—C1—C2—C3	−179.80 (15)	C4—C5—C6—C1	0.7 (3)
C6—C1—C2—C7	176.75 (15)	C1—C2—C7—O1	−21.1 (2)
N1—C1—C2—C7	−3.1 (2)	C3—C2—C7—O1	155.53 (17)
C1—C2—C3—C4	1.3 (3)	C1—C2—C7—O2	160.61 (16)
C7—C2—C3—C4	−175.43 (16)	C3—C2—C7—O2	−22.8 (2)
C2—C3—C4—C5	−1.7 (3)	O1—C7—O2—C8	−1.5 (3)
C3—C4—C5—C6	0.7 (3)	C2—C7—O2—C8	176.80 (16)
C2—C1—C6—C5	−1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O5	0.93	2.68	3.387 (2)	133
C4—H4···O6	0.93	2.71	3.590 (2)	158
C3—H3···O2i	0.93	2.72	3.609 (2)	162
N1—H1A···O3ii	0.89	1.93	2.8218 (18)	178
N1—H1A···O5ii	0.89	2.68	3.190 (2)	118
N1—H1C···O3iii	0.89	2.01	2.9005 (18)	175
N1—H1B···O3iv	0.89	2.09	2.9400 (17)	160
O5—H5O···O6v	0.78 (2)	1.83 (2)	2.6021 (17)	170 (2)
O4—H4O···O6vi	0.72 (2)	1.88 (2)	2.6015 (17)	179 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O5	0.93	2.68	3.387 (2)	133
C4—H4⋯O6	0.93	2.71	3.590 (2)	158
C3—H3⋯O2i	0.93	2.72	3.609 (2)	162
N1—H1A⋯O3ii	0.89	1.93	2.8218 (18)	178
N1—H1A⋯O5ii	0.89	2.68	3.190 (2)	118
N1—H1C⋯O3iii	0.89	2.01	2.9005 (18)	175
N1—H1B⋯O3iv	0.89	2.09	2.9400 (17)	160
O5—H5O⋯O6v	0.78 (2)	1.83 (2)	2.6021 (17)	170 (2)
O4—H4O⋯O6vi	0.72 (2)	1.88 (2)	2.6015 (17)	179 (2)

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