2-Methyl­propan-2-aminium 4-hy­droxy­benzoate

Yu, S.-L.

doi:10.1107/S1600536810022592

organic compounds

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Volume 66| Part 7| July 2010| Page o1706

doi:10.1107/S1600536810022592

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2-Methylpropan-2-aminium 4-hydroxybenzoate

Shu-Lan Yu ^a ^*

^aChemistry Engineering Department, Weifang Vocational College, Weifang 261000, People's Republic of China
^*Correspondence e-mail: crystal_wf@163.com

(Received 10 June 2010; accepted 12 June 2010; online 18 June 2010)

In the crystal of the title molecular salt, C₄H₁₂N⁺·C₇H₅O₃⁻, the cation is linked to three nearby anions by N—H⋯O hydrogen bonds. An O—H⋯O hydrogen bond between anions further consolidates the packing.

Related literature

For a related structure, see: Scholz & Gorls (2002 ).

Experimental

Crystal data

C₄H₁₂N⁺·C₇H₅O₃⁻
M_r = 211.26
Monoclinic, P 2₁ /c
a = 6.8300 (14) Å
b = 9.2790 (19) Å
c = 19.831 (4) Å
β = 99.58 (3)°
V = 1239.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.10 × 0.09 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer
2899 measured reflections
2677 independent reflections
1804 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.168
S = 1.04
2677 reflections
149 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3B⋯O1ⁱ	0.82	1.83	2.621 (2)	163
N1—H1⋯O2ⁱⁱ	0.92 (2)	1.93 (2)	2.835 (2)	168.2 (18)
N1—H3⋯O2	0.94 (2)	1.93 (2)	2.842 (2)	162.2 (18)
N1—H2⋯O1ⁱⁱⁱ	0.87 (2)	1.92 (3)	2.796 (2)	174.7 (19)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+2, -z+1; (iii) x+1, y, z.

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); 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); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022592/hb5493sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022592/hb5493Isup2.hkl

checkCIF report

Related literature top

For a related structure, see: Scholz & Gorls (2002).

Experimental top

A mixture of 2-methylpropan-2-amine(0.02 mol) and 4-hydroxybenzoic acid (0.02 mol) was stirred in ethanol (30 ml) at 353 K for 3 h to afford the title compound (yield 50%). Colourless bars of (I) were obtained by recrystallization from acetone at room temperature.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.

2-Methylpropan-2-aminium 4-hydroxybenzoate top

Crystal data top

C₄H₁₂N⁺·C₇H₅O₃⁻	F(000) = 456
M_r = 211.26	D_x = 1.132 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1804 reflections
a = 6.8300 (14) Å	θ = 2.1–27.0°
b = 9.2790 (19) Å	µ = 0.08 mm⁻¹
c = 19.831 (4) Å	T = 293 K
β = 99.58 (3)°	Bar, colorless
V = 1239.3 (4) Å³	0.10 × 0.09 × 0.08 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	1804 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 27.0°, θ_min = 2.1°
phi and ω scans	h = 0→8
2899 measured reflections	k = 0→11
2677 independent reflections	l = −23→23

Refinement top

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)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.168	w = 1/[σ²(F_o²) + (0.0928P)² + 0.1735P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2677 reflections	Δρ_max = 0.22 e Å⁻³
149 parameters	Δρ_min = −0.29 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: 0.59 (3)

Crystal data top

C₄H₁₂N⁺·C₇H₅O₃⁻	V = 1239.3 (4) Å³
M_r = 211.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.8300 (14) Å	µ = 0.08 mm⁻¹
b = 9.2790 (19) Å	T = 293 K
c = 19.831 (4) Å	0.10 × 0.09 × 0.08 mm
β = 99.58 (3)°

Data collection top

Bruker SMART CCD diffractometer	1804 reflections with I > 2σ(I)
2899 measured reflections	R_int = 0.039
2677 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.168	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.22 e Å⁻³
2677 reflections	Δρ_min = −0.29 e Å⁻³
149 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1770 (3)	0.81042 (19)	0.40216 (9)	0.0475 (4)
C2	0.2054 (2)	0.70697 (18)	0.34696 (8)	0.0435 (4)
C3	0.3911 (3)	0.6882 (2)	0.32850 (10)	0.0618 (6)
H3A	0.4999	0.7372	0.3523	0.074*
C4	0.4170 (3)	0.5976 (3)	0.27512 (12)	0.0728 (7)
H4A	0.5423	0.5872	0.2632	0.087*
C5	0.2577 (3)	0.5225 (2)	0.23940 (10)	0.0571 (5)
C6	0.0722 (3)	0.5367 (2)	0.25849 (10)	0.0558 (5)
H6A	−0.0351	0.4843	0.2359	0.067*
C7	0.0470 (2)	0.6290 (2)	0.31113 (9)	0.0513 (5)
H7A	−0.0785	0.6393	0.3229	0.062*
O1	0.00062 (19)	0.84869 (15)	0.40644 (6)	0.0606 (4)
O2	0.3246 (2)	0.85859 (16)	0.44198 (7)	0.0667 (5)
O3	0.2922 (2)	0.4377 (2)	0.18682 (9)	0.0863 (6)
H3B	0.1865	0.4187	0.1622	0.129*
C8	0.7450 (4)	0.6075 (3)	0.50722 (16)	0.0949 (9)
H8A	0.6109	0.6040	0.4832	0.142*
H8B	0.7693	0.5259	0.5372	0.142*
H8C	0.8352	0.6053	0.4749	0.142*
C9	0.6313 (5)	0.7601 (4)	0.59955 (17)	0.1178 (12)
H9A	0.6486	0.8522	0.6218	0.177*
H9B	0.6563	0.6850	0.6331	0.177*
H9C	0.4977	0.7520	0.5754	0.177*
C10	0.9911 (4)	0.7600 (3)	0.58411 (13)	0.0806 (7)
H10A	1.0103	0.8519	0.6065	0.121*
H10B	1.0772	0.7522	0.5507	0.121*
H10C	1.0213	0.6845	0.6173	0.121*
C11	0.7764 (3)	0.7461 (2)	0.54907 (11)	0.0632 (6)
N1	0.7346 (2)	0.86993 (18)	0.49897 (8)	0.0483 (4)
H1	0.734 (3)	0.958 (2)	0.5202 (10)	0.058*
H2	0.815 (3)	0.869 (2)	0.4690 (12)	0.058*
H3	0.608 (3)	0.859 (2)	0.4718 (10)	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0461 (10)	0.0530 (10)	0.0442 (8)	0.0012 (8)	0.0095 (7)	0.0012 (7)
C2	0.0394 (9)	0.0475 (9)	0.0439 (8)	−0.0014 (7)	0.0077 (7)	0.0004 (7)
C3	0.0401 (10)	0.0804 (13)	0.0662 (11)	−0.0155 (9)	0.0120 (8)	−0.0224 (10)
C4	0.0406 (10)	0.1022 (17)	0.0781 (14)	−0.0061 (10)	0.0176 (9)	−0.0322 (12)
C5	0.0449 (10)	0.0678 (12)	0.0576 (10)	0.0055 (8)	0.0055 (8)	−0.0158 (9)
C6	0.0394 (9)	0.0673 (12)	0.0583 (10)	−0.0050 (8)	0.0008 (7)	−0.0132 (9)
C7	0.0356 (8)	0.0661 (11)	0.0523 (9)	−0.0023 (8)	0.0070 (7)	−0.0036 (8)
O1	0.0513 (8)	0.0813 (10)	0.0505 (7)	0.0161 (7)	0.0122 (6)	−0.0023 (6)
O2	0.0521 (8)	0.0788 (10)	0.0674 (9)	−0.0015 (7)	0.0051 (6)	−0.0267 (7)
O3	0.0537 (8)	0.1141 (13)	0.0890 (11)	0.0104 (8)	0.0058 (7)	−0.0525 (10)
C8	0.0918 (18)	0.0576 (14)	0.127 (2)	−0.0112 (12)	−0.0065 (16)	0.0126 (14)
C9	0.098 (2)	0.161 (3)	0.107 (2)	0.013 (2)	0.0542 (18)	0.056 (2)
C10	0.0671 (14)	0.0876 (16)	0.0802 (15)	0.0001 (12)	−0.0078 (12)	0.0154 (13)
C11	0.0545 (11)	0.0673 (12)	0.0678 (12)	−0.0024 (10)	0.0105 (9)	0.0151 (10)
N1	0.0421 (8)	0.0528 (9)	0.0510 (8)	−0.0009 (7)	0.0108 (7)	−0.0036 (7)

Geometric parameters (Å, º) top

C1—O2	1.255 (2)	C8—H8A	0.9600
C1—O1	1.272 (2)	C8—H8B	0.9600
C1—C2	1.493 (2)	C8—H8C	0.9600
C2—C3	1.388 (2)	C9—C11	1.527 (3)
C2—C7	1.394 (2)	C9—H9A	0.9600
C3—C4	1.386 (3)	C9—H9B	0.9600
C3—H3A	0.9300	C9—H9C	0.9600
C4—C5	1.384 (3)	C10—C11	1.520 (3)
C4—H4A	0.9300	C10—H10A	0.9600
C5—O3	1.358 (2)	C10—H10B	0.9600
C5—C6	1.388 (3)	C10—H10C	0.9600
C6—C7	1.383 (3)	C11—N1	1.515 (2)
C6—H6A	0.9300	N1—H1	0.92 (2)
C7—H7A	0.9300	N1—H2	0.87 (2)
O3—H3B	0.8200	N1—H3	0.94 (2)
C8—C11	1.527 (3)

O2—C1—O1	121.95 (16)	H8A—C8—H8C	109.5
O2—C1—C2	120.11 (16)	H8B—C8—H8C	109.5
O1—C1—C2	117.93 (15)	C11—C9—H9A	109.5
C3—C2—C7	117.80 (15)	C11—C9—H9B	109.5
C3—C2—C1	120.66 (15)	H9A—C9—H9B	109.5
C7—C2—C1	121.53 (15)	C11—C9—H9C	109.5
C4—C3—C2	121.05 (17)	H9A—C9—H9C	109.5
C4—C3—H3A	119.5	H9B—C9—H9C	109.5
C2—C3—H3A	119.5	C11—C10—H10A	109.5
C5—C4—C3	120.47 (18)	C11—C10—H10B	109.5
C5—C4—H4A	119.8	H10A—C10—H10B	109.5
C3—C4—H4A	119.8	C11—C10—H10C	109.5
O3—C5—C4	117.57 (17)	H10A—C10—H10C	109.5
O3—C5—C6	123.22 (17)	H10B—C10—H10C	109.5
C4—C5—C6	119.21 (17)	N1—C11—C10	107.33 (16)
C7—C6—C5	119.93 (16)	N1—C11—C8	106.78 (18)
C7—C6—H6A	120.0	C10—C11—C8	110.92 (19)
C5—C6—H6A	120.0	N1—C11—C9	107.08 (19)
C6—C7—C2	121.50 (16)	C10—C11—C9	112.0 (2)
C6—C7—H7A	119.3	C8—C11—C9	112.4 (2)
C2—C7—H7A	119.3	C11—N1—H1	113.0 (13)
C5—O3—H3B	109.5	C11—N1—H2	111.4 (13)
C11—C8—H8A	109.5	H1—N1—H2	111.9 (19)
C11—C8—H8B	109.5	C11—N1—H3	110.4 (12)
H8A—C8—H8B	109.5	H1—N1—H3	106.4 (18)
C11—C8—H8C	109.5	H2—N1—H3	103.3 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O1ⁱ	0.82	1.83	2.621 (2)	163
N1—H1···O2ⁱⁱ	0.92 (2)	1.93 (2)	2.835 (2)	168.2 (18)
N1—H3···O2	0.94 (2)	1.93 (2)	2.842 (2)	162.2 (18)
N1—H2···O1ⁱⁱⁱ	0.87 (2)	1.92 (3)	2.796 (2)	174.7 (19)

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1, −y+2, −z+1; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₄H₁₂N⁺·C₇H₅O₃⁻
M_r	211.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	6.8300 (14), 9.2790 (19), 19.831 (4)
β (°)	99.58 (3)
V (Å³)	1239.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.10 × 0.09 × 0.08

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2899, 2677, 1804
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.168, 1.04
No. of reflections	2677
No. of parameters	149
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.29

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O1ⁱ	0.82	1.83	2.621 (2)	163
N1—H1···O2ⁱⁱ	0.92 (2)	1.93 (2)	2.835 (2)	168.2 (18)
N1—H3···O2	0.94 (2)	1.93 (2)	2.842 (2)	162.2 (18)
N1—H2···O1ⁱⁱⁱ	0.87 (2)	1.92 (3)	2.796 (2)	174.7 (19)

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1, −y+2, −z+1; (iii) x+1, y, z.

References

Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Scholz, J. & Gorls, H. (2002). Polyhedron, 21, 305–312. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1706

doi:10.1107/S1600536810022592

Open

access