2-Methyl-propan-2-aminium 2-(meth-oxy-carbon-yl)benzoate.

In the title compound, C(4)H(12)N(+)·C(9)H(7)O(4) (-), two C atoms and the N atom of the cation lie on a mirror plane, while all the atoms of the anion are disordered about a mirror plane. In the crystal, N-H⋯O hydrogen bonds link the components into chains along [010]. In the anion, the mean planes of the methoxycarbonyl and carboxylate groups form dihedral angles of 83.0 (2) and 83.2 (2)°, respectively, with the aromatic ring.

Related literature

For the applications of phthalimides and N-substituted phthalimides, see: Lima et al. (2002 ▶). For related structures, see: Li (2011 ▶); Liang (2011 ▶).

Experimental

Crystal data

C4H12N+·C9H7O4 −

M = 253.29

Monoclinic,

a = 9.2939 (8) Å

b = 7.0159 (6) Å

c = 10.5536 (11) Å

β = 103.322 (1)°

V = 669.63 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.49 × 0.43 × 0.32 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.956, T max = 0.971

4353 measured reflections

1797 independent reflections

1137 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.137

S = 1.03

1797 reflections

152 parameters

14 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037688/lh5313sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037688/lh5313Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037688/lh5313Isup3.cml

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

C4H12N+·C9H7O4−	F(000) = 272
Mr = 253.29	Dx = 1.256 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 1362 reflections
a = 9.2939 (8) Å	θ = 2.6–25.8°
b = 7.0159 (6) Å	µ = 0.09 mm−1
c = 10.5536 (11) Å	T = 298 K
β = 103.322 (1)°	Block, colorless
V = 669.63 (11) Å3	0.49 × 0.43 × 0.32 mm
Z = 2

Bruker SMART CCD diffractometer	1797 independent reflections
Radiation source: fine-focus sealed tube	1137 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −12→11
Tmin = 0.956, Tmax = 0.971	k = −9→9
4353 measured reflections	l = −6→14

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0609P)2 + 0.1129P] where P = (Fo2 + 2Fc2)/3
1797 reflections	(Δ/σ)max < 0.001
152 parameters	Δρmax = 0.16 e Å−3
14 restraints	Δρmin = −0.17 e Å−3

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	Occ. (<1)
O1	0.8688 (2)	0.2267 (9)	0.39796 (18)	0.0599 (11)	0.50
O2	0.9747 (2)	0.2711 (10)	0.60624 (19)	0.0596 (10)	0.50
O3	0.8655 (3)	0.1366 (4)	0.8604 (3)	0.0541 (7)	0.50
O4	0.8413 (3)	0.4448 (4)	0.8097 (3)	0.0544 (7)	0.50
C1	0.8655 (3)	0.2433 (7)	0.5222 (2)	0.0440 (7)	0.50
C2	0.8117 (3)	0.2730 (9)	0.7889 (2)	0.0366 (9)	0.50
C3	0.7136 (3)	0.2236 (5)	0.5430 (2)	0.0470 (9)	0.50
C4	0.6905 (3)	0.2377 (6)	0.6689 (2)	0.0407 (6)	0.50
C5	0.5479 (3)	0.2184 (7)	0.6863 (3)	0.0574 (13)	0.50
H5A	0.5315	0.2273	0.7698	0.069*	0.50
C6	0.4291 (3)	0.1862 (4)	0.5818 (3)	0.0547 (9)	0.50
H6A	0.3342	0.1727	0.5955	0.066*	0.50
C7	0.4520 (4)	0.1743 (4)	0.4584 (3)	0.0566 (9)	0.50
H7A	0.3725	0.1551	0.3879	0.068*	0.50
C8	0.5922 (3)	0.1906 (3)	0.4389 (3)	0.0483 (8)	0.50
H8A	0.6070	0.1797	0.3551	0.058*	0.50
C9	1.0136 (3)	0.2437 (12)	0.3673 (3)	0.0716 (11)	0.5
H9A	1.0025	0.2370	0.2747	0.107*	0.50
H9B	1.0762	0.1417	0.4083	0.107*	0.50
H9C	1.0573	0.3637	0.3989	0.107*	0.50
N1	0.87003 (19)	0.7500	0.96516 (19)	0.0428 (5)
C10	0.7457 (2)	0.7500	1.0343 (2)	0.0417 (5)
C11	0.76193 (19)	0.5723 (3)	1.11787 (18)	0.0606 (5)
H11A	0.7587	0.4617	1.0637	0.091*
H11B	0.6826	0.5666	1.1621	0.091*
H11C	0.8547	0.5761	1.1808	0.091*
C12	0.6025 (2)	0.7500	0.9300 (2)	0.0601 (7)
H12A	0.5986	0.8615	0.8766	0.090*	0.50
H12B	0.5200	0.7504	0.9706	0.090*
H12C	0.5983	0.6381	0.8769	0.090*	0.50
H2N	0.8597 (18)	0.643 (2)	0.9127 (18)	0.060 (5)*
H1N	0.960 (3)	0.7500	1.024 (3)	0.060 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0603 (11)	0.080 (3)	0.0415 (9)	−0.011 (2)	0.0155 (8)	−0.014 (2)
O2	0.0444 (9)	0.088 (3)	0.0444 (9)	−0.012 (2)	0.0060 (7)	−0.006 (2)
O3	0.0524 (14)	0.0535 (17)	0.0458 (16)	−0.0050 (13)	−0.0106 (12)	0.0165 (13)
O4	0.0625 (17)	0.0448 (16)	0.0515 (17)	−0.0075 (12)	0.0042 (13)	−0.0091 (12)
C1	0.0504 (12)	0.0467 (15)	0.0338 (12)	0.006 (5)	0.0073 (10)	−0.014 (4)
C2	0.0340 (9)	0.042 (2)	0.0338 (10)	0.0011 (13)	0.0088 (8)	0.0018 (14)
C3	0.0417 (12)	0.059 (3)	0.0369 (12)	0.0012 (18)	0.0015 (9)	−0.0022 (19)
C4	0.0364 (10)	0.0458 (15)	0.0364 (11)	0.005 (3)	0.0014 (8)	0.001 (3)
C5	0.0396 (12)	0.086 (4)	0.0453 (13)	−0.001 (2)	0.0064 (10)	0.001 (2)
C6	0.0357 (14)	0.056 (2)	0.068 (2)	−0.0041 (11)	0.0018 (14)	−0.0015 (14)
C7	0.0465 (16)	0.059 (2)	0.0528 (18)	−0.0036 (13)	−0.0126 (14)	−0.0040 (14)
C8	0.0556 (17)	0.046 (2)	0.0366 (14)	−0.0011 (12)	−0.0028 (12)	−0.0038 (11)
C9	0.0723 (18)	0.086 (3)	0.0611 (19)	−0.015 (5)	0.0253 (15)	0.032 (5)
N1	0.0340 (9)	0.0543 (12)	0.0378 (10)	0.000	0.0037 (7)	0.000
C10	0.0327 (10)	0.0499 (12)	0.0418 (11)	0.000	0.0069 (8)	0.000
C11	0.0581 (10)	0.0617 (11)	0.0619 (10)	−0.0050 (8)	0.0137 (8)	0.0120 (9)
C12	0.0361 (11)	0.0756 (17)	0.0636 (15)	0.000	0.0010 (11)	0.000

O1—C1	1.323 (3)	C8—H8A	0.9300
O1—C9	1.460 (3)	C9—H9A	0.9600
O2—C1	1.200 (3)	C9—H9B	0.9600
O3—C2	1.249 (6)	C9—H9C	0.9600
O4—C2	1.244 (7)	N1—C10	1.501 (3)
C1—C3	1.484 (4)	N1—H2N	0.925 (18)
C2—C4	1.509 (3)	N1—H1N	0.92 (3)
C3—C4	1.397 (4)	C10—C11i	1.515 (2)
C3—C8	1.400 (4)	C10—C11	1.515 (2)
C4—C5	1.386 (4)	C10—C12	1.519 (3)
C5—C6	1.388 (4)	C11—H11A	0.9600
C5—H5A	0.9300	C11—H11B	0.9600
C6—C7	1.370 (5)	C11—H11C	0.9600
C6—H6A	0.9300	C12—H12A	0.9600
C7—C8	1.369 (5)	C12—H12B	0.9600
C7—H7A	0.9300	C12—H12C	0.9600
C1—O1—C9	116.4 (2)	O1—C9—H9B	109.5
O2—C1—O1	122.5 (2)	H9A—C9—H9B	109.5
O2—C1—C3	125.3 (2)	O1—C9—H9C	109.5
O1—C1—C3	112.2 (2)	H9A—C9—H9C	109.5
O4—C2—O3	126.5 (4)	H9B—C9—H9C	109.5
O4—C2—C4	113.5 (3)	C10—N1—H2N	107.8 (11)
O3—C2—C4	119.9 (3)	C10—N1—H1N	110.8 (15)
C4—C3—C8	119.0 (3)	H2N—N1—H1N	110.9 (13)
C4—C3—C1	119.6 (2)	N1—C10—C11i	107.38 (11)
C8—C3—C1	121.4 (2)	N1—C10—C11	107.38 (11)
C5—C4—C3	118.7 (2)	C11i—C10—C11	110.77 (19)
C5—C4—C2	117.2 (2)	N1—C10—C12	106.99 (18)
C3—C4—C2	124.1 (2)	C11i—C10—C12	112.01 (11)
C4—C5—C6	121.4 (3)	C11—C10—C12	112.01 (11)
C4—C5—H5A	119.3	C10—C11—H11A	109.5
C6—C5—H5A	119.3	C10—C11—H11B	109.5
C7—C6—C5	119.7 (3)	H11A—C11—H11B	109.5
C7—C6—H6A	120.1	C10—C11—H11C	109.5
C5—C6—H6A	120.1	H11A—C11—H11C	109.5
C8—C7—C6	120.0 (3)	H11B—C11—H11C	109.5
C8—C7—H7A	120.0	C10—C12—H12A	109.5
C6—C7—H7A	120.0	C10—C12—H12B	109.5
C7—C8—C3	121.2 (3)	H12A—C12—H12B	109.5
C7—C8—H8A	119.4	C10—C12—H12C	109.5
C3—C8—H8A	119.4	H12A—C12—H12C	109.5
O1—C9—H9A	109.5	H12B—C12—H12C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N···O4	0.925 (18)	1.749 (19)	2.674 (3)	178.3 (17)
N1—H2N···O3ii	0.925 (18)	2.042 (18)	2.926 (3)	159.4 (16)
N1—H1N···O3iii	0.92 (3)	1.96 (2)	2.825 (3)	156.(1)
N1—H1N···O3iv	0.92 (3)	1.96 (2)	2.825 (3)	156.(1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2N⋯O4	0.925 (18)	1.749 (19)	2.674 (3)	178.3 (17)
N1—H2N⋯O3i	0.925 (18)	2.042 (18)	2.926 (3)	159.4 (16)
N1—H1N⋯O3ii	0.92 (3)	1.96 (2)	2.825 (3)	156 (1)
N1—H1N⋯O3iii	0.92 (3)	1.96 (2)	2.825 (3)	156 (1)

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