Dimethyl-ammonium 3-carb-oxy-benzoate.

The asymmetric unit of the title organic salt, C(2)H(8)N(+)·C(8)H(5)O(4) (-), consists of two dimethyl-ammonium cations and two 3-carb-oxy-benzoate anions. The 3-carb-oxy-benzoate anions are linked via strong inter-molecular and nearly symmetrical O-H⋯O hydrogen bonds forming infinite chains parallel to [111]. Neighbouring chains are further connected by the dimethyl-ammonium cations via N-H⋯O bonds, resulting in a double-chain-like structure. The dihedral angles of all carboxylate groups with respect to the phenylene rings are in the range 7.9 (1)-20.48 (9)°.

Related literature

For supra­molecular structures comprising 3-carb­oxy­benzo­ates, see: Guo et al. (2010 ▶); Liu et al. (2007 ▶); Weyna et al. (2009 ▶). For similar chain-like structures, see: Ballabh et al. (2005 ▶). For hydrolysis of formamides, see: Cottineau et al. (2011 ▶); Hine et al. (1981 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For hydrogen bonding, see: Gilli & Gilli (2009 ▶).

Experimental

Crystal data

C2H8N+·n class="Chemical">C8H5O4 −

M = 211.21

Triclinic,

a = 8.439 (5) Å

b = 10.133 (8) Å

c = 12.304 (9) Å

α = 91.858 (14)°

β = 94.599 (17)°

γ = 90.009 (14)°

V = 1048.2 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.32 × 0.21 × 0.09 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2011 ▶) T min = 0.684, T max = 0.746

13304 measured reflections

6417 independent reflections

4906 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.125

S = 1.06

6417 reflections

283 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXLE (Hübschle et al., 2011 ▶) and SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681202096X/su2413sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202096X/su2413Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202096X/su2413Isup3.cml

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

C2H8N+·C8H5O4−	Z = 4
Mr = 211.21	F(000) = 448
Triclinic, P1	Dx = 1.338 Mg m−3
a = 8.439 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.133 (8) Å	Cell parameters from 832 reflections
c = 12.304 (9) Å	θ = 2.6–31.1°
α = 91.858 (14)°	µ = 0.10 mm−1
β = 94.599 (17)°	T = 100 K
γ = 90.009 (14)°	Plate, colourless
V = 1048.2 (13) Å3	0.32 × 0.21 × 0.09 mm

Bruker SMART APEX CCD diffractometer	6417 independent reflections
Radiation source: fine-focus sealed tube	4906 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω scans	θmax = 31.8°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −12→12
Tmin = 0.684, Tmax = 0.746	k = −14→14
13304 measured reflections	l = −17→18

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0443P)2 + 0.3839P] where P = (Fo2 + 2Fc2)/3
6417 reflections	(Δ/σ)max < 0.001
283 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.29 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
C1	0.59587 (16)	0.02460 (14)	−0.25653 (10)	0.0162 (3)
C2	0.58993 (16)	0.13501 (13)	−0.17228 (10)	0.0156 (2)
C3	0.48388 (15)	0.12628 (13)	−0.09138 (10)	0.0146 (2)
H3	0.4153	0.0519	−0.0910	0.018*
C4	0.47801 (16)	0.22626 (13)	−0.01100 (10)	0.0155 (2)
C5	0.57738 (17)	0.33635 (14)	−0.01340 (11)	0.0180 (3)
H5	0.5745	0.4043	0.0414	0.022*
C6	0.68042 (18)	0.34716 (14)	−0.09543 (12)	0.0207 (3)
H6	0.7458	0.4232	−0.0976	0.025*
C7	0.68748 (17)	0.24595 (14)	−0.17441 (11)	0.0186 (3)
H7	0.7589	0.2525	−0.2299	0.022*
C8	0.35934 (16)	0.21816 (14)	0.07316 (11)	0.0171 (3)
C9	−0.11755 (16)	0.80121 (13)	0.53099 (11)	0.0163 (3)
C10	−0.11194 (15)	0.71996 (13)	0.42712 (10)	0.0153 (2)
C11	0.01076 (16)	0.62967 (13)	0.41715 (11)	0.0152 (2)
H11	0.0899	0.6204	0.4758	0.018*
C12	0.01843 (16)	0.55276 (13)	0.32181 (11)	0.0156 (2)
C13	−0.09707 (17)	0.56792 (14)	0.23523 (11)	0.0183 (3)
H13	−0.0916	0.5167	0.1696	0.022*
C14	−0.21941 (18)	0.65736 (15)	0.24494 (11)	0.0200 (3)
H14	−0.2979	0.6673	0.1860	0.024*
C15	−0.22774 (17)	0.73288 (14)	0.34092 (11)	0.0181 (3)
H15	−0.3127	0.7934	0.3476	0.022*
C16	0.15174 (16)	0.45605 (14)	0.31194 (11)	0.0166 (3)
C17	0.60139 (18)	0.23158 (16)	0.50279 (12)	0.0246 (3)
H17A	0.5285	0.1660	0.5280	0.037*
H17B	0.6147	0.3049	0.5567	0.037*
H17C	0.7048	0.1905	0.4936	0.037*
C18	0.64148 (18)	0.37914 (15)	0.35102 (12)	0.0230 (3)
H18A	0.7438	0.3373	0.3395	0.035*
H18B	0.6586	0.4550	0.4021	0.035*
H18C	0.5924	0.4091	0.2813	0.035*
C19	0.07030 (19)	1.03645 (15)	0.80345 (14)	0.0268 (3)
H19A	0.0896	1.0796	0.8757	0.040*
H19B	−0.0110	1.0855	0.7601	0.040*
H19C	0.1691	1.0350	0.7667	0.040*
C20	0.13291 (19)	0.82098 (16)	0.88063 (13)	0.0262 (3)
H20A	0.0922	0.7313	0.8874	0.039*
H20B	0.1530	0.8628	0.9533	0.039*
H20C	0.2322	0.8171	0.8444	0.039*
N1	0.53500 (14)	0.28220 (12)	0.39679 (9)	0.0178 (2)
H1A	0.4386	0.3216	0.4061	0.021*
H1B	0.5174	0.2123	0.3477	0.021*
N2	0.01442 (14)	0.89893 (12)	0.81537 (9)	0.0178 (2)
H2A	−0.0795	0.9006	0.8486	0.021*
H2B	−0.0050	0.8590	0.7474	0.021*
O1	0.72388 (12)	0.01992 (10)	−0.30648 (8)	0.0205 (2)
O2	0.48067 (12)	−0.05209 (10)	−0.27252 (8)	0.0221 (2)
O3	0.38017 (13)	0.30395 (11)	0.15297 (8)	0.0237 (2)
H3A	0.255 (4)	0.332 (3)	0.198 (2)	0.092 (10)*
O4	0.24967 (12)	0.13580 (10)	0.06142 (8)	0.0210 (2)
O5	−0.24912 (12)	0.86489 (11)	0.53935 (9)	0.0223 (2)
H5A	−0.260 (3)	0.933 (2)	0.618 (2)	0.066 (8)*
O6	−0.00266 (12)	0.80375 (11)	0.59990 (8)	0.0212 (2)
O7	0.13688 (12)	0.38054 (11)	0.22481 (8)	0.0220 (2)
O8	0.26436 (12)	0.45389 (10)	0.38262 (8)	0.0204 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0177 (6)	0.0175 (6)	0.0131 (5)	0.0032 (5)	0.0005 (5)	−0.0018 (5)
C2	0.0163 (6)	0.0160 (6)	0.0140 (6)	0.0037 (5)	−0.0003 (5)	−0.0020 (5)
C3	0.0143 (6)	0.0145 (6)	0.0147 (6)	0.0016 (5)	−0.0001 (4)	−0.0020 (5)
C4	0.0159 (6)	0.0156 (6)	0.0146 (6)	0.0046 (5)	−0.0005 (5)	−0.0014 (5)
C5	0.0211 (7)	0.0142 (6)	0.0181 (6)	0.0023 (5)	−0.0009 (5)	−0.0025 (5)
C6	0.0234 (7)	0.0153 (6)	0.0234 (7)	−0.0017 (5)	0.0016 (5)	−0.0001 (5)
C7	0.0203 (6)	0.0180 (6)	0.0178 (6)	0.0001 (5)	0.0039 (5)	0.0005 (5)
C8	0.0156 (6)	0.0198 (6)	0.0155 (6)	0.0058 (5)	0.0000 (5)	−0.0021 (5)
C9	0.0167 (6)	0.0157 (6)	0.0167 (6)	0.0000 (5)	0.0030 (5)	−0.0015 (5)
C10	0.0147 (6)	0.0164 (6)	0.0148 (6)	−0.0012 (5)	0.0019 (5)	−0.0015 (5)
C11	0.0141 (6)	0.0159 (6)	0.0157 (6)	−0.0005 (5)	0.0015 (5)	−0.0012 (5)
C12	0.0157 (6)	0.0156 (6)	0.0155 (6)	−0.0012 (5)	0.0030 (5)	−0.0016 (5)
C13	0.0227 (7)	0.0189 (6)	0.0129 (6)	0.0006 (5)	0.0011 (5)	−0.0025 (5)
C14	0.0221 (7)	0.0221 (7)	0.0152 (6)	0.0026 (5)	−0.0029 (5)	−0.0001 (5)
C15	0.0174 (6)	0.0185 (6)	0.0183 (6)	0.0023 (5)	0.0008 (5)	−0.0003 (5)
C16	0.0157 (6)	0.0181 (6)	0.0164 (6)	−0.0006 (5)	0.0049 (5)	−0.0026 (5)
C17	0.0206 (7)	0.0306 (8)	0.0221 (7)	−0.0038 (6)	−0.0030 (5)	0.0021 (6)
C18	0.0219 (7)	0.0226 (7)	0.0242 (7)	−0.0064 (6)	0.0000 (6)	0.0001 (6)
C19	0.0229 (7)	0.0225 (7)	0.0340 (8)	−0.0042 (6)	−0.0045 (6)	0.0024 (6)
C20	0.0233 (7)	0.0266 (8)	0.0271 (7)	0.0006 (6)	−0.0080 (6)	−0.0003 (6)
N1	0.0151 (5)	0.0197 (6)	0.0182 (5)	−0.0001 (4)	0.0002 (4)	−0.0036 (4)
N2	0.0156 (5)	0.0219 (6)	0.0156 (5)	−0.0007 (4)	0.0006 (4)	−0.0027 (4)
O1	0.0183 (5)	0.0244 (5)	0.0189 (5)	0.0018 (4)	0.0052 (4)	−0.0058 (4)
O2	0.0196 (5)	0.0229 (5)	0.0231 (5)	−0.0016 (4)	0.0027 (4)	−0.0090 (4)
O3	0.0203 (5)	0.0294 (6)	0.0209 (5)	0.0012 (4)	0.0038 (4)	−0.0111 (4)
O4	0.0194 (5)	0.0249 (5)	0.0188 (5)	−0.0002 (4)	0.0042 (4)	−0.0034 (4)
O5	0.0165 (5)	0.0254 (5)	0.0241 (5)	0.0048 (4)	0.0013 (4)	−0.0095 (4)
O6	0.0171 (5)	0.0276 (6)	0.0179 (5)	0.0029 (4)	−0.0006 (4)	−0.0064 (4)
O7	0.0201 (5)	0.0247 (5)	0.0205 (5)	0.0024 (4)	0.0024 (4)	−0.0099 (4)
O8	0.0179 (5)	0.0213 (5)	0.0214 (5)	0.0043 (4)	0.0006 (4)	−0.0051 (4)

C1—O2	1.2438 (18)	C14—H14	0.9500
C1—O1	1.2850 (17)	C15—H15	0.9500
C1—C2	1.504 (2)	C16—O8	1.2364 (17)
C2—C7	1.395 (2)	C16—O7	1.2945 (17)
C2—C3	1.396 (2)	C17—N1	1.485 (2)
C3—C4	1.3964 (19)	C17—H17A	0.9800
C3—H3	0.9500	C17—H17B	0.9800
C4—C5	1.398 (2)	C17—H17C	0.9800
C4—C8	1.501 (2)	C18—N1	1.485 (2)
C5—C6	1.391 (2)	C18—H18A	0.9800
C5—H5	0.9500	C18—H18B	0.9800
C6—C7	1.394 (2)	C18—H18C	0.9800
C6—H6	0.9500	C19—N2	1.487 (2)
C7—H7	0.9500	C19—H19A	0.9800
C8—O4	1.2427 (18)	C19—H19B	0.9800
C8—O3	1.2915 (18)	C19—H19C	0.9800
C9—O6	1.2354 (17)	C20—N2	1.477 (2)
C9—O5	1.2938 (17)	C20—H20A	0.9800
C9—C10	1.502 (2)	C20—H20B	0.9800
C10—C11	1.392 (2)	C20—H20C	0.9800
C10—C15	1.393 (2)	N1—H1A	0.9200
C11—C12	1.3931 (19)	N1—H1B	0.9200
C11—H11	0.9500	N2—H2A	0.9200
C12—C13	1.397 (2)	N2—H2B	0.9200
C12—C16	1.502 (2)	O3—H3A	1.26 (3)
C13—C14	1.384 (2)	O5—H5A	1.18 (2)
C13—H13	0.9500	O7—H3A	1.18 (3)
C14—C15	1.393 (2)
O2—C1—O1	125.98 (13)	C14—C15—H15	119.9
O2—C1—C2	119.15 (12)	O8—C16—O7	125.23 (13)
O1—C1—C2	114.87 (12)	O8—C16—C12	120.54 (12)
C7—C2—C3	119.73 (12)	O7—C16—C12	114.22 (12)
C7—C2—C1	121.09 (13)	N1—C17—H17A	109.5
C3—C2—C1	119.17 (12)	N1—C17—H17B	109.5
C2—C3—C4	120.34 (13)	H17A—C17—H17B	109.5
C2—C3—H3	119.8	N1—C17—H17C	109.5
C4—C3—H3	119.8	H17A—C17—H17C	109.5
C3—C4—C5	119.39 (13)	H17B—C17—H17C	109.5
C3—C4—C8	119.84 (13)	N1—C18—H18A	109.5
C5—C4—C8	120.69 (12)	N1—C18—H18B	109.5
C6—C5—C4	120.52 (13)	H18A—C18—H18B	109.5
C6—C5—H5	119.7	N1—C18—H18C	109.5
C4—C5—H5	119.7	H18A—C18—H18C	109.5
C5—C6—C7	119.77 (13)	H18B—C18—H18C	109.5
C5—C6—H6	120.1	N2—C19—H19A	109.5
C7—C6—H6	120.1	N2—C19—H19B	109.5
C6—C7—C2	120.22 (13)	H19A—C19—H19B	109.5
C6—C7—H7	119.9	N2—C19—H19C	109.5
C2—C7—H7	119.9	H19A—C19—H19C	109.5
O4—C8—O3	125.16 (13)	H19B—C19—H19C	109.5
O4—C8—C4	120.20 (12)	N2—C20—H20A	109.5
O3—C8—C4	114.61 (13)	N2—C20—H20B	109.5
O6—C9—O5	125.27 (13)	H20A—C20—H20B	109.5
O6—C9—C10	120.41 (13)	N2—C20—H20C	109.5
O5—C9—C10	114.32 (12)	H20A—C20—H20C	109.5
C11—C10—C15	119.48 (12)	H20B—C20—H20C	109.5
C11—C10—C9	119.35 (12)	C17—N1—C18	112.80 (12)
C15—C10—C9	121.16 (13)	C17—N1—H1A	109.0
C10—C11—C12	120.50 (12)	C18—N1—H1A	109.0
C10—C11—H11	119.7	C17—N1—H1B	109.0
C12—C11—H11	119.7	C18—N1—H1B	109.0
C11—C12—C13	119.54 (13)	H1A—N1—H1B	107.8
C11—C12—C16	119.98 (12)	C20—N2—C19	111.54 (12)
C13—C12—C16	120.48 (12)	C20—N2—H2A	109.3
C14—C13—C12	120.12 (13)	C19—N2—H2A	109.3
C14—C13—H13	119.9	C20—N2—H2B	109.3
C12—C13—H13	119.9	C19—N2—H2B	109.3
C13—C14—C15	120.16 (13)	H2A—N2—H2B	108.0
C13—C14—H14	119.9	C8—O3—H3A	114.0 (13)
C15—C14—H14	119.9	C9—O5—H5A	117.8 (12)
C10—C15—C14	120.19 (13)	C16—O7—H3A	115.5 (14)
C10—C15—H15	119.9
O2—C1—C2—C7	−159.33 (13)	O6—C9—C10—C11	11.4 (2)
O1—C1—C2—C7	20.32 (18)	O5—C9—C10—C11	−168.79 (12)
O2—C1—C2—C3	20.12 (19)	O6—C9—C10—C15	−169.00 (13)
O1—C1—C2—C3	−160.23 (12)	O5—C9—C10—C15	10.86 (19)
C7—C2—C3—C4	−1.72 (19)	C15—C10—C11—C12	0.1 (2)
C1—C2—C3—C4	178.82 (12)	C9—C10—C11—C12	179.78 (12)
C2—C3—C4—C5	1.13 (19)	C10—C11—C12—C13	0.8 (2)
C2—C3—C4—C8	177.77 (12)	C10—C11—C12—C16	179.79 (12)
C3—C4—C5—C6	0.5 (2)	C11—C12—C13—C14	−1.0 (2)
C8—C4—C5—C6	−176.10 (13)	C16—C12—C13—C14	−179.93 (13)
C4—C5—C6—C7	−1.6 (2)	C12—C13—C14—C15	0.2 (2)
C5—C6—C7—C2	1.0 (2)	C11—C10—C15—C14	−0.9 (2)
C3—C2—C7—C6	0.7 (2)	C9—C10—C15—C14	179.43 (13)
C1—C2—C7—C6	−179.87 (13)	C13—C14—C15—C10	0.8 (2)
C3—C4—C8—O4	−12.05 (19)	C11—C12—C16—O8	−7.9 (2)
C5—C4—C8—O4	164.55 (13)	C13—C12—C16—O8	171.06 (13)
C3—C4—C8—O3	169.72 (12)	C11—C12—C16—O7	172.93 (12)
C5—C4—C8—O3	−13.68 (18)	C13—C12—C16—O7	−8.10 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O8	0.92	2.00	2.869 (2)	157
N1—H1B···O2i	0.92	1.84	2.744 (2)	166
N2—H2A···O4ii	0.92	1.93	2.822 (2)	164
N2—H2B···O6	0.92	1.88	2.784 (2)	166
O7—H3A···O3	1.18 (3)	1.26 (3)	2.4177 (19)	166 (3)
O7—H3A···O4	1.18 (3)	2.56 (3)	3.329 (2)	121.1 (18)
O5—H5A···O1iii	1.18 (2)	1.27 (2)	2.4483 (19)	171 (2)
O5—H5A···O2iii	1.18 (2)	2.66 (2)	3.462 (2)	124.2 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O8	0.92	2.00	2.869 (2)	157
N1—H1B⋯O2i	0.92	1.84	2.744 (2)	166
N2—H2A⋯O4ii	0.92	1.93	2.822 (2)	164
N2—H2B⋯O6	0.92	1.88	2.784 (2)	166
O7—H3A⋯O3	1.18 (3)	1.26 (3)	2.4177 (19)	166 (3)
O7—H3A⋯O4	1.18 (3)	2.56 (3)	3.329 (2)	121.1 (18)
O5—H5A⋯O1iii	1.18 (2)	1.27 (2)	2.4483 (19)	171 (2)
O5—H5A⋯O2iii	1.18 (2)	2.66 (2)	3.462 (2)	124.2 (15)

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