Dieth-yl(hy-droxy)ammonium 3-carb-oxy-benzoate.

In the title molecular compound, C(4)H(12)NO(+)·C(8)H(5)O(4) (-), the N,N-dieth-yl(hy-droxy)ammonium cation (DTHA) is linked to the 3-carb-oxy-benzoate anion (HBDL) by O-H⋯O and N-H⋯O hydrogen bonds with a graph-set motif R(2) (2)(7). In the crystal, helical chains are formed by O-H⋯O hydrogen bonds, propagating along [010]. The crystal structure is further stabilized by π-π inter-actions between inversion-related HBDL benzene rings [centroid-centroid distance = 3.900 (4) Å] and C-H⋯O inter-actions.

Related literature

For supra­molecular structures comprising benzene-dicarb­oxy­lic acids, see: Karpova et al. (2004 ▶); Bourne et al. (2001 ▶); Jin et al. (2005 ▶); Dale et al. (2004 ▶); Shan et al. (2002 ▶); Yuge et al. (2006 ▶); Zhao et al. (2007 ▶). For graph-set analysis, see: Etter (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C4H12NO+·C8H5O4 −

M = 255.27

Monoclinic,

a = 9.535 (7) Å

b = 11.937 (9) Å

c = 11.660 (9) Å

β = 96.959 (15)°

V = 1317.4 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 273 K

0.34 × 0.15 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.967, T max = 0.977

6749 measured reflections

2317 independent reflections

1912 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.203

S = 1.19

2317 reflections

167 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (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 (Bruker, 2007 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030746/su2200sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030746/su2200Isup2.hkl

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

C4H12NO+·C8H5O4−	F(000) = 544
Mr = 255.27	Dx = 1.287 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3574 reflections
a = 9.535 (7) Å	θ = 2.1–25.0°
b = 11.937 (9) Å	µ = 0.10 mm−1
c = 11.660 (9) Å	T = 273 K
β = 96.959 (15)°	Block, colorless
V = 1317.4 (17) Å3	0.34 × 0.15 × 0.14 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2317 independent reflections
Radiation source: fine-focus sealed tube	1912 reflections with I > 2σ(I)
graphite	Rint = 0.029
phi and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
Tmin = 0.967, Tmax = 0.977	k = −14→13
6749 measured reflections	l = −13→9

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.203	H-atom parameters constrained
S = 1.19	w = 1/[σ2(Fo2) + (0.0962P)2 + 0.4181P] where P = (Fo2 + 2Fc2)/3
2317 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.26 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
O2	0.8613 (3)	0.64114 (19)	−0.0032 (2)	0.0693 (8)
O3	0.4161 (3)	0.39290 (18)	0.2751 (2)	0.0755 (9)
O4	0.4378 (2)	0.22073 (16)	0.2114 (2)	0.0594 (7)
H4	0.3865	0.2064	0.2611	0.089*
C1	0.7731 (3)	0.6172 (2)	0.0625 (3)	0.0418 (7)
C2	0.7101 (3)	0.5018 (2)	0.0565 (2)	0.0358 (7)
C3	0.6177 (3)	0.4682 (2)	0.1322 (2)	0.0363 (7)
H3	0.5928	0.5181	0.1876	0.044*
C4	0.5616 (3)	0.3611 (2)	0.1267 (2)	0.0364 (7)
C5	0.5951 (3)	0.2889 (2)	0.0422 (3)	0.0481 (8)
H5A	0.5568	0.2172	0.0373	0.058*
C6	0.6849 (4)	0.3223 (3)	−0.0350 (3)	0.0555 (9)
H6	0.7061	0.2734	−0.0926	0.067*
C7	0.7434 (3)	0.4276 (2)	−0.0276 (3)	0.0483 (8)
H7	0.8056	0.4492	−0.0791	0.058*
C8	0.4642 (3)	0.3282 (2)	0.2117 (3)	0.0429 (7)
O1	0.7347 (2)	0.68498 (17)	0.13536 (19)	0.0534 (6)
O5	0.9635 (3)	0.83592 (18)	0.0383 (2)	0.0613 (7)
H5	0.9340	0.7740	0.0166	0.092*
N1	0.8850 (3)	0.8758 (2)	0.1251 (2)	0.0504 (7)
H1	0.8150	0.8258	0.1335	0.060*
C9	1.0396 (4)	0.7722 (4)	0.2759 (4)	0.0870 (13)
H9A	0.9648	0.7224	0.2905	0.130*
H9B	1.1032	0.7821	0.3456	0.130*
H9C	1.0900	0.7410	0.2170	0.130*
C10	0.9787 (4)	0.8832 (3)	0.2364 (3)	0.0697 (11)
H10A	0.9251	0.9130	0.2951	0.084*
H10B	1.0551	0.9349	0.2277	0.084*
C11	0.7195 (5)	0.9731 (4)	−0.0227 (4)	0.0870 (13)
H11A	0.7696	0.9443	−0.0830	0.131*
H11B	0.6806	1.0452	−0.0450	0.131*
H11C	0.6446	0.9226	−0.0101	0.131*
C12	0.8190 (4)	0.9843 (3)	0.0861 (3)	0.0635 (10)
H12A	0.8927	1.0374	0.0735	0.076*
H12B	0.7680	1.0141	0.1465	0.076*

	U11	U22	U33	U12	U13	U23
O2	0.0955 (18)	0.0479 (14)	0.0763 (17)	−0.0257 (12)	0.0577 (15)	−0.0171 (12)
O3	0.106 (2)	0.0381 (13)	0.097 (2)	−0.0105 (12)	0.0701 (17)	−0.0130 (12)
O4	0.0767 (17)	0.0336 (12)	0.0770 (18)	−0.0074 (10)	0.0459 (13)	−0.0033 (10)
C1	0.0488 (17)	0.0335 (16)	0.0462 (17)	0.0001 (13)	0.0186 (14)	−0.0018 (13)
C2	0.0364 (14)	0.0309 (15)	0.0406 (16)	0.0006 (11)	0.0072 (12)	0.0016 (12)
C3	0.0409 (15)	0.0283 (15)	0.0414 (16)	0.0034 (11)	0.0123 (12)	−0.0022 (12)
C4	0.0360 (14)	0.0310 (15)	0.0432 (16)	0.0028 (11)	0.0085 (12)	0.0016 (12)
C5	0.0527 (18)	0.0322 (16)	0.063 (2)	−0.0059 (13)	0.0199 (15)	−0.0078 (14)
C6	0.072 (2)	0.0399 (18)	0.061 (2)	−0.0105 (15)	0.0341 (17)	−0.0197 (15)
C7	0.0584 (19)	0.0402 (17)	0.0521 (19)	−0.0041 (14)	0.0293 (15)	−0.0060 (14)
C8	0.0490 (17)	0.0308 (16)	0.0515 (18)	−0.0005 (13)	0.0168 (14)	−0.0026 (13)
O1	0.0594 (13)	0.0350 (12)	0.0728 (15)	−0.0094 (10)	0.0364 (12)	−0.0134 (10)
O5	0.0832 (17)	0.0478 (14)	0.0618 (15)	−0.0209 (12)	0.0448 (13)	−0.0137 (11)
N1	0.0623 (17)	0.0404 (15)	0.0540 (16)	−0.0215 (12)	0.0296 (13)	−0.0096 (12)
C9	0.077 (3)	0.115 (4)	0.069 (3)	0.006 (3)	0.011 (2)	0.003 (3)
C10	0.077 (3)	0.079 (3)	0.055 (2)	−0.024 (2)	0.0163 (19)	−0.0136 (19)
C11	0.099 (3)	0.068 (3)	0.093 (3)	−0.009 (2)	0.007 (3)	0.007 (2)
C12	0.083 (2)	0.0390 (19)	0.075 (2)	−0.0208 (17)	0.035 (2)	−0.0081 (16)

O2—C1	1.238 (3)	O5—N1	1.412 (3)
O3—C8	1.198 (3)	O5—H5	0.8200
O4—C8	1.307 (4)	N1—C10	1.486 (5)
O4—H4	0.8200	N1—C12	1.487 (5)
C1—O1	1.259 (3)	N1—H1	0.9100
C1—C2	1.502 (4)	C9—C10	1.496 (6)
C2—C3	1.380 (4)	C9—H9A	0.9600
C2—C7	1.386 (4)	C9—H9B	0.9600
C3—C4	1.384 (4)	C9—H9C	0.9600
C3—H3	0.9300	C10—H10A	0.9700
C4—C5	1.375 (4)	C10—H10B	0.9700
C4—C8	1.491 (4)	C11—C12	1.495 (6)
C5—C6	1.374 (4)	C11—H11A	0.9600
C5—H5A	0.9300	C11—H11B	0.9600
C6—C7	1.374 (4)	C11—H11C	0.9600
C6—H6	0.9300	C12—H12A	0.9700
C7—H7	0.9300	C12—H12B	0.9700
C8—O4—H4	109.5	C10—N1—C12	113.8 (3)
O2—C1—O1	123.0 (3)	O5—N1—H1	108.4
O2—C1—C2	118.7 (2)	C10—N1—H1	108.4
O1—C1—C2	118.3 (2)	C12—N1—H1	108.4
C3—C2—C7	119.1 (3)	C10—C9—H9A	109.5
C3—C2—C1	121.3 (2)	C10—C9—H9B	109.5
C7—C2—C1	119.6 (2)	H9A—C9—H9B	109.5
C2—C3—C4	120.8 (3)	C10—C9—H9C	109.5
C2—C3—H3	119.6	H9A—C9—H9C	109.5
C4—C3—H3	119.6	H9B—C9—H9C	109.5
C5—C4—C3	119.3 (3)	N1—C10—C9	112.7 (3)
C5—C4—C8	121.9 (3)	N1—C10—H10A	109.0
C3—C4—C8	118.8 (2)	C9—C10—H10A	109.0
C6—C5—C4	120.3 (3)	N1—C10—H10B	109.0
C6—C5—H5A	119.8	C9—C10—H10B	109.0
C4—C5—H5A	119.8	H10A—C10—H10B	107.8
C7—C6—C5	120.3 (3)	C12—C11—H11A	109.5
C7—C6—H6	119.8	C12—C11—H11B	109.5
C5—C6—H6	119.8	H11A—C11—H11B	109.5
C6—C7—C2	120.2 (3)	C12—C11—H11C	109.5
C6—C7—H7	119.9	H11A—C11—H11C	109.5
C2—C7—H7	119.9	H11B—C11—H11C	109.5
O3—C8—O4	123.1 (3)	N1—C12—C11	112.5 (3)
O3—C8—C4	123.8 (3)	N1—C12—H12A	109.1
O4—C8—C4	113.1 (2)	C11—C12—H12A	109.1
N1—O5—H5	109.5	N1—C12—H12B	109.1
O5—N1—C10	109.4 (3)	C11—C12—H12B	109.1
O5—N1—C12	108.4 (2)	H12A—C12—H12B	107.8
O2—C1—C2—C3	176.0 (3)	C5—C6—C7—C2	−1.3 (5)
O1—C1—C2—C3	−3.1 (4)	C3—C2—C7—C6	0.1 (5)
O2—C1—C2—C7	−4.8 (4)	C1—C2—C7—C6	−179.1 (3)
O1—C1—C2—C7	176.0 (3)	C5—C4—C8—O3	−168.5 (3)
C7—C2—C3—C4	1.6 (4)	C3—C4—C8—O3	10.4 (4)
C1—C2—C3—C4	−179.2 (3)	C5—C4—C8—O4	12.4 (4)
C2—C3—C4—C5	−2.1 (4)	C3—C4—C8—O4	−168.7 (3)
C2—C3—C4—C8	178.9 (2)	O5—N1—C10—C9	−60.7 (4)
C3—C4—C5—C6	0.9 (4)	C12—N1—C10—C9	177.9 (3)
C8—C4—C5—C6	179.8 (3)	O5—N1—C12—C11	61.2 (4)
C4—C5—C6—C7	0.8 (5)	C10—N1—C12—C11	−176.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.91	1.85	2.702 (4)	155
O5—H5···O2	0.82	1.74	2.545 (4)	169
O4—H4···O1i	0.82	1.79	2.606 (4)	175
C10—H10A···O2ii	0.97	2.58	3.373 (5)	139
C12—H12A···O5iii	0.97	2.51	3.426 (5)	157
C12—H12B···O3iv	0.97	2.53	3.117 (5)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.91	1.85	2.702 (4)	155
O5—H5⋯O2	0.82	1.74	2.545 (4)	169
O4—H4⋯O1i	0.82	1.79	2.606 (4)	175
C10—H10A⋯O2ii	0.97	2.58	3.373 (5)	139
C12—H12A⋯O5iii	0.97	2.51	3.426 (5)	157
C12—H12B⋯O3iv	0.97	2.53	3.117 (5)	119

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