3-Methyl-anilinium hydrogen phthalate.

The asymmetric unit of the title salt, C(7)H(10)N(+)·C(8)H(5)O(4) (-), consists of two 3-methyl-phenyl-ammonium cations and two hydrogen phthalate anions. There are strong intra-molecular O-H⋯O hydrogen bonds in the virtually planar (r.m.s. deviations = 0.054 Å) phthalate anions. In the crystal, the cations and anions are connected via an extensive sytem of N-H⋯O hydrogen bonds into a corrugated layer extended parallel to (001).

Related literature

The title compound was investigated as part of work looking for new ferroelectric compounds. For background to ferroelectric compounds consisting of organic cations and inorganic anions, see: Fu et al. (2011 ▶); Ye et al. (2010 ▶). For a related structure, see: Kadirvelraj et al. (1996 ▶).

Experimental

Crystal data

C7H10N+·n class="Chemical">C8H5O4 −

M = 273.28

Monoclinic,

a = 7.9325 (16) Å

b = 17.931 (4) Å

c = 19.575 (4) Å

β = 93.37 (3)°

V = 2779.5 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.36 × 0.32 × 0.28 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.963, T max = 0.971

22962 measured reflections

4906 independent reflections

2489 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.165

S = 1.03

4906 reflections

368 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811054353/gk2431sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054353/gk2431Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054353/gk2431Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536811054353/gk2431Isup4.cml

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

C7H10N+·C8H5O4−	F(000) = 1152
Mr = 273.28	Dx = 1.306 Mg m−3
Monoclinic, P21/n	Melting point: 413 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.9325 (16) Å	Cell parameters from 4906 reflections
b = 17.931 (4) Å	θ = 3.4–25.0°
c = 19.575 (4) Å	µ = 0.10 mm−1
β = 93.37 (3)°	T = 293 K
V = 2779.5 (10) Å3	Block, colourless
Z = 8	0.36 × 0.32 × 0.28 mm

Rigaku Mercury2 diffractometer	4906 independent reflections
Radiation source: fine-focus sealed tube	2489 reflections with I > 2σ(I)
graphite	Rint = 0.090
Detector resolution: 13.6612 pixels mm-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −21→21
Tmin = 0.963, Tmax = 0.971	l = −23→23
22962 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066	H-atom parameters constrained
wR(F2) = 0.165	w = 1/[σ2(Fo2) + (0.0672P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.003
4906 reflections	Δρmax = 0.18 e Å−3
368 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0038 (9)

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 > 2sigma(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
N2	0.4142 (3)	0.70027 (13)	0.16189 (12)	0.0493 (7)
H2A	0.3797	0.7446	0.1761	0.074*
H2B	0.4874	0.6809	0.1932	0.074*
H2C	0.3258	0.6700	0.1556	0.074*
N1	−0.0859 (3)	0.85234 (13)	0.15519 (12)	0.0471 (7)
H1A	−0.0165	0.8742	0.1865	0.071*
H1B	−0.1163	0.8078	0.1704	0.071*
H1C	−0.1773	0.8805	0.1473	0.071*
O2	0.8571 (3)	0.14134 (13)	0.23666 (12)	0.0671 (7)
O6	0.3588 (3)	0.41675 (12)	0.24495 (12)	0.0680 (7)
O3	0.8400 (3)	0.02633 (13)	0.17473 (13)	0.0627 (7)
H3	0.8455	0.0637	0.1989	0.094*
O4	0.6480 (3)	−0.04790 (12)	0.13023 (12)	0.0701 (7)
O1	0.6943 (3)	0.22617 (13)	0.27712 (13)	0.0703 (7)
O5	0.2074 (3)	0.32453 (13)	0.27620 (13)	0.0780 (8)
O7	0.3337 (3)	0.53387 (12)	0.18671 (13)	0.0626 (7)
H7	0.3424	0.4936	0.2065	0.094*
O8	0.1401 (3)	0.60431 (12)	0.13895 (12)	0.0676 (7)
C10	0.0608 (3)	0.41746 (16)	0.21047 (14)	0.0378 (7)
C1	0.5594 (4)	0.13815 (16)	0.20140 (14)	0.0399 (8)
C15	0.0443 (4)	0.48752 (16)	0.17754 (14)	0.0402 (7)
C6	0.5481 (4)	0.06991 (16)	0.16526 (15)	0.0401 (7)
C22	0.0006 (4)	0.84311 (18)	0.09148 (15)	0.0443 (8)
C9	0.2169 (4)	0.38404 (18)	0.24608 (16)	0.0459 (8)
C11	−0.0827 (4)	0.37315 (18)	0.21255 (16)	0.0522 (9)
H11	−0.0725	0.3266	0.2333	0.063*
C2	0.4145 (4)	0.18156 (18)	0.20308 (16)	0.0514 (9)
H2	0.4205	0.2266	0.2266	0.062*
C7	0.6849 (4)	0.01263 (19)	0.15662 (16)	0.0480 (8)
C29	0.4959 (4)	0.70911 (18)	0.09736 (16)	0.0469 (8)
C8	0.7121 (4)	0.17078 (18)	0.24167 (16)	0.0461 (8)
C23	0.0200 (4)	0.77319 (18)	0.06485 (17)	0.0517 (9)
H23	−0.0179	0.7314	0.0876	0.062*
C3	0.2629 (4)	0.1606 (2)	0.17137 (18)	0.0626 (10)
H3A	0.1686	0.1912	0.1732	0.075*
C12	−0.2372 (4)	0.3946 (2)	0.18566 (18)	0.0617 (10)
H12	−0.3299	0.3631	0.1877	0.074*
C30	0.5465 (4)	0.64590 (19)	0.06421 (17)	0.0558 (9)
H30	0.5298	0.5994	0.0838	0.067*
C28	0.5197 (4)	0.77878 (19)	0.0716 (2)	0.0651 (10)
H28	0.4882	0.8211	0.0951	0.078*
C25	0.6213 (5)	0.6503 (3)	0.0026 (2)	0.0732 (11)
C14	−0.1142 (4)	0.50854 (19)	0.15125 (16)	0.0567 (9)
H14	−0.1270	0.5547	0.1300	0.068*
C13	−0.2539 (4)	0.4634 (2)	0.15549 (18)	0.0662 (10)
H13	−0.3591	0.4796	0.1379	0.079*
C5	0.3929 (4)	0.04985 (18)	0.13383 (17)	0.0555 (9)
H5	0.3842	0.0051	0.1099	0.067*
C21	0.0560 (4)	0.9060 (2)	0.06061 (19)	0.0663 (10)
H21	0.0413	0.9527	0.0800	0.080*
C19	0.1539 (5)	0.8296 (3)	−0.02783 (19)	0.0838 (13)
H19	0.2068	0.8255	−0.0688	0.101*
C18	0.0977 (4)	0.7657 (2)	0.0029 (2)	0.0682 (11)
C4	0.2521 (4)	0.0941 (2)	0.13703 (19)	0.0672 (11)
H4	0.1497	0.0790	0.1159	0.081*
C20	0.1342 (5)	0.8988 (3)	0.0001 (2)	0.0880 (13)
H20	0.1736	0.9408	−0.0218	0.106*
C27	0.5930 (5)	0.7842 (3)	0.0088 (3)	0.0940 (15)
H27	0.6089	0.8306	−0.0109	0.113*
C26	0.6419 (5)	0.7202 (3)	−0.0240 (2)	0.0900 (14)
H26	0.6907	0.7248	−0.0659	0.108*
C24	0.6775 (6)	0.5823 (3)	−0.0342 (2)	0.1177 (18)
H24A	0.5976	0.5428	−0.0290	0.176*
H24B	0.7864	0.5670	−0.0152	0.176*
H24C	0.6846	0.5936	−0.0819	0.176*
C16	0.1788 (4)	0.54521 (18)	0.16718 (16)	0.0465 (8)
C17	0.1206 (5)	0.6898 (3)	−0.0274 (2)	0.1080 (16)
H17A	0.0371	0.6821	−0.0642	0.162*
H17B	0.1080	0.6525	0.0072	0.162*
H17C	0.2313	0.6861	−0.0444	0.162*

	U11	U22	U33	U12	U13	U23
N2	0.0534 (17)	0.0370 (15)	0.0571 (17)	0.0049 (13)	−0.0004 (14)	0.0010 (13)
N1	0.0494 (16)	0.0363 (15)	0.0553 (17)	−0.0015 (13)	−0.0004 (13)	0.0001 (13)
O2	0.0426 (14)	0.0666 (16)	0.0910 (18)	0.0052 (13)	−0.0060 (13)	−0.0292 (14)
O6	0.0423 (14)	0.0593 (15)	0.101 (2)	−0.0084 (12)	−0.0082 (13)	0.0324 (14)
O3	0.0503 (15)	0.0542 (16)	0.0834 (19)	0.0053 (12)	0.0017 (13)	−0.0211 (13)
O4	0.0704 (17)	0.0445 (15)	0.0935 (19)	0.0018 (13)	−0.0101 (14)	−0.0154 (14)
O1	0.0647 (16)	0.0536 (15)	0.0921 (19)	0.0035 (13)	−0.0002 (13)	−0.0288 (14)
O5	0.0611 (17)	0.0530 (16)	0.119 (2)	−0.0025 (13)	−0.0001 (15)	0.0312 (16)
O7	0.0471 (15)	0.0452 (14)	0.095 (2)	−0.0076 (12)	−0.0034 (13)	0.0204 (13)
O8	0.0647 (17)	0.0446 (14)	0.0925 (19)	−0.0009 (12)	−0.0043 (13)	0.0181 (13)
C10	0.0354 (18)	0.0393 (18)	0.0392 (17)	−0.0020 (15)	0.0062 (14)	−0.0048 (14)
C1	0.0398 (19)	0.0389 (18)	0.0416 (18)	0.0002 (15)	0.0091 (15)	0.0057 (15)
C15	0.0421 (19)	0.0412 (19)	0.0380 (17)	0.0019 (16)	0.0075 (14)	−0.0056 (15)
C6	0.0393 (19)	0.0383 (18)	0.0429 (18)	0.0005 (15)	0.0036 (15)	0.0084 (15)
C22	0.0355 (18)	0.053 (2)	0.0440 (19)	0.0000 (16)	−0.0028 (15)	0.0059 (17)
C9	0.044 (2)	0.042 (2)	0.052 (2)	−0.0034 (17)	0.0049 (16)	0.0038 (16)
C11	0.048 (2)	0.052 (2)	0.057 (2)	−0.0032 (18)	0.0058 (17)	0.0013 (17)
C2	0.048 (2)	0.049 (2)	0.058 (2)	0.0047 (18)	0.0083 (17)	0.0028 (17)
C7	0.049 (2)	0.045 (2)	0.050 (2)	−0.0040 (18)	0.0025 (16)	0.0032 (17)
C29	0.0395 (19)	0.047 (2)	0.053 (2)	−0.0051 (16)	−0.0031 (16)	0.0107 (17)
C8	0.049 (2)	0.0370 (19)	0.052 (2)	0.0021 (17)	0.0058 (17)	−0.0005 (16)
C23	0.046 (2)	0.050 (2)	0.058 (2)	−0.0005 (17)	−0.0047 (17)	−0.0075 (18)
C3	0.040 (2)	0.069 (3)	0.080 (3)	0.010 (2)	0.0075 (18)	0.011 (2)
C12	0.041 (2)	0.072 (3)	0.072 (3)	−0.011 (2)	0.0047 (18)	−0.003 (2)
C30	0.059 (2)	0.051 (2)	0.058 (2)	−0.0056 (19)	0.0037 (18)	0.0004 (19)
C28	0.056 (2)	0.051 (2)	0.088 (3)	−0.0011 (19)	−0.001 (2)	0.023 (2)
C25	0.065 (3)	0.102 (3)	0.053 (2)	−0.008 (2)	0.006 (2)	−0.007 (3)
C14	0.047 (2)	0.060 (2)	0.062 (2)	0.0070 (19)	−0.0002 (18)	0.0053 (18)
C13	0.036 (2)	0.087 (3)	0.074 (3)	0.009 (2)	−0.0050 (18)	0.000 (2)
C5	0.048 (2)	0.048 (2)	0.069 (2)	−0.0042 (18)	−0.0068 (18)	0.0001 (18)
C21	0.065 (3)	0.060 (2)	0.075 (3)	0.000 (2)	0.009 (2)	0.019 (2)
C19	0.065 (3)	0.139 (4)	0.048 (2)	0.017 (3)	0.013 (2)	0.016 (3)
C18	0.053 (2)	0.095 (3)	0.055 (2)	0.018 (2)	−0.008 (2)	−0.020 (2)
C4	0.047 (2)	0.070 (3)	0.083 (3)	−0.003 (2)	−0.009 (2)	0.005 (2)
C20	0.081 (3)	0.105 (4)	0.080 (3)	0.006 (3)	0.018 (3)	0.035 (3)
C27	0.070 (3)	0.097 (4)	0.115 (4)	−0.007 (3)	0.006 (3)	0.065 (3)
C26	0.064 (3)	0.137 (4)	0.069 (3)	0.000 (3)	0.003 (2)	0.028 (3)
C24	0.109 (4)	0.149 (4)	0.099 (3)	−0.023 (3)	0.041 (3)	−0.058 (3)
C16	0.049 (2)	0.044 (2)	0.046 (2)	0.0031 (18)	0.0020 (17)	−0.0047 (16)
C17	0.103 (4)	0.128 (4)	0.092 (3)	0.027 (3)	−0.002 (3)	−0.054 (3)

N2—C29	1.462 (4)	C29—C30	1.377 (4)
N2—H2A	0.8900	C23—C18	1.399 (5)
N2—H2B	0.8900	C23—H23	0.9300
N2—H2C	0.8900	C3—C4	1.368 (4)
N1—C22	1.468 (4)	C3—H3A	0.9300
N1—H1A	0.8900	C12—C13	1.371 (5)
N1—H1B	0.8900	C12—H12	0.9300
N1—H1C	0.8900	C30—C25	1.377 (5)
O2—C8	1.275 (3)	C30—H30	0.9300
O6—C9	1.271 (3)	C28—C27	1.394 (5)
O3—C7	1.284 (3)	C28—H28	0.9300
O3—H3	0.8200	C25—C26	1.372 (5)
O4—C7	1.230 (3)	C25—C24	1.496 (5)
O1—C8	1.225 (3)	C14—C13	1.379 (4)
O5—C9	1.223 (3)	C14—H14	0.9300
O7—C16	1.281 (3)	C13—H13	0.9300
O7—H7	0.8200	C5—C4	1.375 (4)
O8—C16	1.226 (3)	C5—H5	0.9300
C10—C11	1.390 (4)	C21—C20	1.375 (5)
C10—C15	1.414 (4)	C21—H21	0.9300
C10—C9	1.509 (4)	C19—C20	1.367 (5)
C1—C2	1.390 (4)	C19—C18	1.381 (5)
C1—C6	1.413 (4)	C19—H19	0.9300
C1—C8	1.522 (4)	C18—C17	1.500 (5)
C15—C14	1.382 (4)	C4—H4	0.9300
C15—C16	1.508 (4)	C20—H20	0.9300
C6—C5	1.391 (4)	C27—C26	1.381 (6)
C6—C7	1.511 (4)	C27—H27	0.9300
C22—C21	1.364 (4)	C26—H26	0.9300
C22—C23	1.370 (4)	C24—H24A	0.9600
C11—C12	1.361 (4)	C24—H24B	0.9600
C11—H11	0.9300	C24—H24C	0.9600
C2—C3	1.373 (4)	C17—H17A	0.9600
C2—H2	0.9300	C17—H17B	0.9600
C29—C28	1.364 (4)	C17—H17C	0.9600
C29—N2—H2A	109.5	C13—C12—H12	120.5
C29—N2—H2B	109.5	C29—C30—C25	121.2 (3)
H2A—N2—H2B	109.5	C29—C30—H30	119.4
C29—N2—H2C	109.5	C25—C30—H30	119.4
H2A—N2—H2C	109.5	C29—C28—C27	117.6 (4)
H2B—N2—H2C	109.5	C29—C28—H28	121.2
C22—N1—H1A	109.5	C27—C28—H28	121.2
C22—N1—H1B	109.5	C26—C25—C30	116.9 (4)
H1A—N1—H1B	109.5	C26—C25—C24	121.0 (4)
C22—N1—H1C	109.5	C30—C25—C24	122.1 (4)
H1A—N1—H1C	109.5	C13—C14—C15	122.3 (3)
H1B—N1—H1C	109.5	C13—C14—H14	118.8
C7—O3—H3	109.5	C15—C14—H14	118.8
C16—O7—H7	109.5	C12—C13—C14	119.7 (3)
C11—C10—C15	117.8 (3)	C12—C13—H13	120.1
C11—C10—C9	114.2 (3)	C14—C13—H13	120.1
C15—C10—C9	127.9 (3)	C4—C5—C6	122.1 (3)
C2—C1—C6	117.9 (3)	C4—C5—H5	119.0
C2—C1—C8	114.0 (3)	C6—C5—H5	119.0
C6—C1—C8	128.1 (3)	C22—C21—C20	118.5 (4)
C14—C15—C10	118.0 (3)	C22—C21—H21	120.7
C14—C15—C16	113.4 (3)	C20—C21—H21	120.7
C10—C15—C16	128.5 (3)	C20—C19—C18	122.1 (4)
C5—C6—C1	118.3 (3)	C20—C19—H19	119.0
C5—C6—C7	113.4 (3)	C18—C19—H19	119.0
C1—C6—C7	128.3 (3)	C19—C18—C23	117.9 (4)
C21—C22—C23	122.8 (3)	C19—C18—C17	122.1 (4)
C21—C22—N1	117.5 (3)	C23—C18—C17	120.0 (4)
C23—C22—N1	119.7 (3)	C3—C4—C5	119.8 (3)
O5—C9—O6	119.4 (3)	C3—C4—H4	120.1
O5—C9—C10	119.8 (3)	C5—C4—H4	120.1
O6—C9—C10	120.8 (3)	C19—C20—C21	119.8 (4)
C12—C11—C10	123.2 (3)	C19—C20—H20	120.1
C12—C11—H11	118.4	C21—C20—H20	120.1
C10—C11—H11	118.4	C26—C27—C28	119.7 (4)
C3—C2—C1	122.6 (3)	C26—C27—H27	120.1
C3—C2—H2	118.7	C28—C27—H27	120.1
C1—C2—H2	118.7	C25—C26—C27	122.6 (4)
O4—C7—O3	119.0 (3)	C25—C26—H26	118.7
O4—C7—C6	119.5 (3)	C27—C26—H26	118.7
O3—C7—C6	121.4 (3)	C25—C24—H24A	109.5
C28—C29—C30	121.9 (3)	C25—C24—H24B	109.5
C28—C29—N2	119.8 (3)	H24A—C24—H24B	109.5
C30—C29—N2	118.3 (3)	C25—C24—H24C	109.5
O1—C8—O2	120.9 (3)	H24A—C24—H24C	109.5
O1—C8—C1	119.4 (3)	H24B—C24—H24C	109.5
O2—C8—C1	119.7 (3)	O8—C16—O7	118.8 (3)
C22—C23—C18	118.9 (3)	O8—C16—C15	119.5 (3)
C22—C23—H23	120.6	O7—C16—C15	121.6 (3)
C18—C23—H23	120.6	C18—C17—H17A	109.5
C4—C3—C2	119.3 (3)	C18—C17—H17B	109.5
C4—C3—H3A	120.4	H17A—C17—H17B	109.5
C2—C3—H3A	120.4	C18—C17—H17C	109.5
C11—C12—C13	118.9 (3)	H17A—C17—H17C	109.5
C11—C12—H12	120.5	H17B—C17—H17C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5i	0.89	1.87	2.739 (3)	166
N2—H2B···O2ii	0.89	1.93	2.815 (3)	178
N2—H2C···O8	0.89	1.90	2.789 (3)	178
N1—H1A···O6i	0.89	1.94	2.826 (3)	177
N1—H1B···O1i	0.89	1.91	2.784 (3)	166
N1—H1C···O4iii	0.89	1.90	2.788 (3)	172
O3—H3···O2	0.82	1.58	2.392 (3)	173
O7—H7···O6	0.82	1.57	2.392 (3)	180

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O5i	0.89	1.87	2.739 (3)	166
N2—H2B⋯O2ii	0.89	1.93	2.815 (3)	178
N2—H2C⋯O8	0.89	1.90	2.789 (3)	178
N1—H1A⋯O6i	0.89	1.94	2.826 (3)	177
N1—H1B⋯O1i	0.89	1.91	2.784 (3)	166
N1—H1C⋯O4iii	0.89	1.90	2.788 (3)	172
O3—H3⋯O2	0.82	1.58	2.392 (3)	173
O7—H7⋯O6	0.82	1.57	2.392 (3)	180

Symmetry codes: (i) ; (ii) ; (iii) .