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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o1984
https://doi.org/10.1107/S1600536812024403

4-Methyl­anilinium 2-carb­­oxy­acetate

Ying-Chun Wanga*

aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: chenxinyuanseu@yahoo.com.cn

(Received 19 May 2012; accepted 29 May 2012; online 2 June 2012)

During the formation of the title salt, C7H10N+·C3H3O4−, an H atom of a carboxyl group was transferred to the amino group. All non-H atoms of the cation are essentially coplanar [r.m.s. deviation = 0.007 (4) Å]. The mean planes of the carboxyl­ate and carboxyl groups of the anion form a dihedral of 69.67 (1)°. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds connect the anions and cations, forming a two-dimensional network parallel to the bc plane.

Related literature

For the structures and properties of related compounds, see: Chen et al. (2001[Chen, Z.-F., Li, B.-Q., Xie, Y.-R., Xiong, R.-G., You, X.-Z. & Feng, X.-L. (2001). Inorg. Chem. Commun. 4, 346-349.]); Wang et al. (2002[Wang, L.-Z., Wang, X.-S., Li, Y.-H., Bai, Z.-P., Xiong, R.-G., Xiong, M. & Li, G.-W. (2002). Chin. J. Inorg. Chem. 18, 1191-1194.]); Xue et al. (2002[Xue, X., Abrahams, B. F., Xiong, R.-G. & You, X.-Z. (2002). Aust. J. Chem. 55, 495-497.]); Huang et al. (1999[Huang, S.-P.-D., Xiong, R.-G., Han, J.-D. & Weiner, B. R. (1999). Inorg. Chim. Acta, 294, 95-98.]); Zhang et al. (2001[Zhang, J., Xiong, R.-G., Chen, X.-T., Che, C.-M., Xue, Z.-L. & You, X.-Z. (2001). Organometallics, 20, 4118-4121.]); Ye et al. (2008[Ye, Q., Fu, D.-W., Hang, T., Xiong, R.-G., Chan, P. W. H. & Huang, S. P. D. (2008). Inorg. Chem. 47, 772-774.]).

[Scheme 1]

Experimental

Crystal data

  • C7H10N+·C3H3O4−

  • Mr = 211.21

  • Monoclinic, P 21 /c

  • a = 12.7937 (19) Å

  • b = 9.2742 (16) Å

  • c = 8.5194 (17) Å

  • β = 104.853 (2)°

  • V = 977.1 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 123 K

  • 0.10 × 0.05 × 0.05 mm
Data collection

  • Rigaku Mercury2 diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.910, Tmax = 1.000

  • 7787 measured reflections

  • 2228 independent reflections

  • 1943 reflections with I > 2σ(I)

  • Rint = 0.031
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.111

  • S = 1.08

  • 2228 reflections

  • 138 parameters

  • 4 restraints

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O4i 0.82 1.72 2.5353 (15) 175
N1—H1A⋯O2ii 0.91 1.94 2.8377 (17) 167
N1—H1B⋯O3iii 0.91 1.86 2.7642 (17) 171
N1—H1C⋯O1iv 0.91 2.21 2.8600 (17) 128
N1—H1C⋯O3v 0.91 2.32 2.9872 (17) 130
N1—H1C⋯O4iv 0.91 2.41 2.9655 (17) 120
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iv) -x+2, -y+1, -z+1; (v) x, y-1, z.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812024403/lh5480sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812024403/lh5480Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812024403/lh5480Isup3.cml

checkCIF report


Comment top

Simple organic salts containing strong intrermolecular H-bonds have attracted attention as materials which display ferroelectric-paraelectric phase transitions (Chen et al., 2001; Huang, et al. 1999; Zhang, et al. 2001). With the purpose of obtaining phase transition crystals of organic salts, various organic molecules have been studied and a series of new crystal materials have been elaborated (Wang, et al. 2002; Xue, et al. 2002; Ye, et al. 2008). Herein, we present the synthesis and crystal structure of the title compound.

The molecular structure of the title salt is shown in Fig. 1. The asymmetric unit is composed of one 4-methylanilinium cation and one 2-carboxyacetate anion. All non-H atoms of the cation are essentially coplanar [r.m.s. deviation = 0.007 (4)Å ]. The mean planes of the carboxylate and carboxyl groups of the anion form a dihedral of 69.67 (1)°. In the crystal, N—H···O and O—H···O hydrogen bonds connect anions and cations to form a two-dimensional network parallel to the bc-plane (Fig. 2 and Table 1).

Related literature top

For the structures and properties of related compounds, see: Chen et al. (2001); Wang et al. (2002); Xue et al. (2002); Huang et al. (1999); Zhang et al. (2001); Ye et al. (2008).

Experimental top

Malonic acid (10 mmol), 4-toluidine (10 mmol) and ethanol (50 mL) were added to a 100mL flask. The mixture was stirred at 333K for 2 h, and then the precipitate was filtrated off. Colourless crystals suitable for X-ray diffraction were obtained by slow evaporation of the solution.

Refinement top

H atoms attached to C atoms were placed in idealized positions and treated as riding with C–H = 0.95 Å (aromatic), C–H = 0.98 Å (methyl) and C–H = 0.99 Å (methylene) with Uiso(H)=1.2Ueq(C except methyl), Uiso(H)=1.5Ueq(C methyl). The positional parameters of the H atoms (N and O) were refined freely. And in the last stages of the refinement, they were restrained with H—N = 0.91 (2)Å and H—O = 0.82 (2)Å with Uiso(H)=1.5Ueq(N and O).

Structure description top

Simple organic salts containing strong intrermolecular H-bonds have attracted attention as materials which display ferroelectric-paraelectric phase transitions (Chen et al., 2001; Huang, et al. 1999; Zhang, et al. 2001). With the purpose of obtaining phase transition crystals of organic salts, various organic molecules have been studied and a series of new crystal materials have been elaborated (Wang, et al. 2002; Xue, et al. 2002; Ye, et al. 2008). Herein, we present the synthesis and crystal structure of the title compound.

The molecular structure of the title salt is shown in Fig. 1. The asymmetric unit is composed of one 4-methylanilinium cation and one 2-carboxyacetate anion. All non-H atoms of the cation are essentially coplanar [r.m.s. deviation = 0.007 (4)Å ]. The mean planes of the carboxylate and carboxyl groups of the anion form a dihedral of 69.67 (1)°. In the crystal, N—H···O and O—H···O hydrogen bonds connect anions and cations to form a two-dimensional network parallel to the bc-plane (Fig. 2 and Table 1).

For the structures and properties of related compounds, see: Chen et al. (2001); Wang et al. (2002); Xue et al. (2002); Huang et al. (1999); Zhang et al. (2001); Ye et al. (2008).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the asymmetric unit with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed along the a axis showing hydrogen bonds as dashed lines.
4-Methylanilinium 2-carboxyacetate top
Crystal data top
C7H10N+·C3H3O4−F(000) = 448
Mr = 211.21Dx = 1.436 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2228 reflections
a = 12.7937 (19) Åθ = 2.8–27.5°
b = 9.2742 (16) ŵ = 0.11 mm−1
c = 8.5194 (17) ÅT = 123 K
β = 104.853 (2)°Block, colorless
V = 977.1 (3) Å30.10 × 0.05 × 0.05 mm
Z = 4
Data collection top
Rigaku Mercury2
diffractometer		2228 independent reflections
Radiation source: fine-focus sealed tube1943 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 2.8°
CCD profile fitting scansh = −14→16
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −11→12
Tmin = 0.910, Tmax = 1.000l = −11→11
7787 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0567P)2 + 0.2948P]
where P = (Fo2 + 2Fc2)/3
2228 reflections(Δ/σ)max < 0.001
138 parametersΔρmax = 0.28 e Å−3
4 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C7H10N+·C3H3O4−V = 977.1 (3) Å3
Mr = 211.21Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.7937 (19) ŵ = 0.11 mm−1
b = 9.2742 (16) ÅT = 123 K
c = 8.5194 (17) Å0.10 × 0.05 × 0.05 mm
β = 104.853 (2)°
Data collection top
Rigaku Mercury2
diffractometer		2228 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		1943 reflections with I > 2σ(I)
Tmin = 0.910, Tmax = 1.000Rint = 0.031
7787 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0424 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.08Δρmax = 0.28 e Å−3
2228 reflectionsΔρmin = −0.24 e Å−3
138 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.00549 (8)0.64322 (11)0.40536 (12)0.0154 (3)
H11.01860.56940.36080.023*
N10.83328 (10)0.19556 (13)0.69727 (15)0.0149 (3)
H1A0.82930.11100.74950.022*
H1B0.85210.26780.77140.022*
H1C0.88390.18780.63970.022*
C10.52657 (13)0.28907 (18)0.37780 (18)0.0188 (3)
O20.82906 (9)0.58930 (12)0.31709 (13)0.0184 (3)
C20.60240 (14)0.39772 (18)0.4318 (2)0.0228 (4)
H2A0.58490.49410.39720.027*
O30.87706 (9)1.06665 (11)0.39914 (12)0.0164 (3)
C30.70340 (13)0.36805 (17)0.53566 (19)0.0199 (3)
H3A0.75460.44310.57090.024*
O40.94461 (9)0.92360 (11)0.23717 (12)0.0157 (3)
C40.72805 (11)0.22776 (16)0.58657 (17)0.0141 (3)
C50.65550 (13)0.11751 (17)0.5333 (2)0.0198 (3)
H5A0.67360.02120.56760.024*
C60.55545 (13)0.14905 (18)0.42871 (19)0.0209 (4)
H6A0.50560.07290.39110.025*
C70.41642 (14)0.31810 (19)0.2661 (2)0.0259 (4)
H7A0.39520.41770.28060.039*
H7B0.36350.25180.29200.039*
H7C0.41900.30360.15320.039*
C80.90197 (12)0.67134 (15)0.38432 (16)0.0135 (3)
C90.88015 (12)0.81514 (16)0.45071 (17)0.0139 (3)
H9A0.92510.82340.56370.017*
H9B0.80350.81810.45430.017*
C100.90250 (11)0.94594 (15)0.35453 (16)0.0126 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0161 (5)0.0117 (5)0.0190 (5)0.0001 (4)0.0057 (4)−0.0020 (4)
N10.0140 (6)0.0135 (6)0.0168 (6)−0.0006 (5)0.0033 (5)0.0004 (5)
C10.0168 (8)0.0219 (8)0.0164 (7)0.0007 (6)0.0018 (6)0.0005 (6)
O20.0168 (6)0.0151 (6)0.0217 (6)−0.0021 (4)0.0022 (4)−0.0024 (4)
C20.0230 (8)0.0161 (8)0.0253 (8)0.0018 (6)−0.0012 (6)0.0032 (6)
O30.0203 (6)0.0123 (5)0.0161 (5)0.0022 (4)0.0037 (4)−0.0007 (4)
C30.0210 (8)0.0156 (8)0.0200 (7)−0.0039 (6)−0.0002 (6)0.0000 (6)
O40.0206 (6)0.0134 (5)0.0143 (5)−0.0004 (4)0.0066 (4)−0.0001 (4)
C40.0125 (7)0.0166 (7)0.0133 (6)0.0011 (5)0.0035 (5)−0.0005 (5)
C50.0174 (8)0.0156 (8)0.0249 (8)−0.0001 (6)0.0024 (6)0.0021 (6)
C60.0175 (8)0.0181 (8)0.0249 (8)−0.0049 (6)0.0014 (6)0.0004 (6)
C70.0195 (8)0.0264 (9)0.0267 (8)0.0004 (7)−0.0036 (7)0.0049 (7)
C80.0175 (7)0.0126 (7)0.0105 (6)−0.0016 (5)0.0039 (5)0.0025 (5)
C90.0154 (7)0.0134 (7)0.0132 (6)−0.0006 (5)0.0044 (5)0.0001 (5)
C100.0105 (6)0.0126 (7)0.0126 (6)−0.0006 (5)−0.0010 (5)0.0000 (5)
Geometric parameters (Å, º) top
O1—C81.3162 (18)C3—H3A0.9500
O1—H10.8202O4—C101.2684 (18)
N1—C41.4629 (18)C4—C51.377 (2)
N1—H1A0.9100C5—C61.390 (2)
N1—H1B0.9100C5—H5A0.9500
N1—H1C0.9100C6—H6A0.9500
C1—C61.389 (2)C7—H7A0.9800
C1—C21.393 (2)C7—H7B0.9800
C1—C71.509 (2)C7—H7C0.9800
O2—C81.2260 (18)C8—C91.502 (2)
C2—C31.393 (2)C9—C101.531 (2)
C2—H2A0.9500C9—H9A0.9900
O3—C101.2518 (18)C9—H9B0.9900
C3—C41.382 (2)
C8—O1—H1114.8C1—C6—C5121.63 (15)
C4—N1—H1A109.5C1—C6—H6A119.2
C4—N1—H1B109.5C5—C6—H6A119.2
H1A—N1—H1B109.5C1—C7—H7A109.5
C4—N1—H1C109.5C1—C7—H7B109.5
H1A—N1—H1C109.5H7A—C7—H7B109.5
H1B—N1—H1C109.5C1—C7—H7C109.5
C6—C1—C2117.79 (14)H7A—C7—H7C109.5
C6—C1—C7119.64 (14)H7B—C7—H7C109.5
C2—C1—C7122.57 (15)O2—C8—O1124.00 (14)
C1—C2—C3121.40 (15)O2—C8—C9122.29 (14)
C1—C2—H2A119.3O1—C8—C9113.71 (12)
C3—C2—H2A119.3C8—C9—C10115.06 (12)
C4—C3—C2119.01 (15)C8—C9—H9A108.5
C4—C3—H3A120.5C10—C9—H9A108.5
C2—C3—H3A120.5C8—C9—H9B108.5
C5—C4—C3121.01 (14)C10—C9—H9B108.5
C5—C4—N1119.47 (13)H9A—C9—H9B107.5
C3—C4—N1119.52 (13)O3—C10—O4125.55 (13)
C4—C5—C6119.14 (14)O3—C10—C9116.57 (13)
C4—C5—H5A120.4O4—C10—C9117.88 (12)
C6—C5—H5A120.4
C6—C1—C2—C3−1.0 (3)C2—C1—C6—C51.5 (2)
C7—C1—C2—C3179.67 (16)C7—C1—C6—C5−179.12 (16)
C1—C2—C3—C4−0.5 (3)C4—C5—C6—C1−0.6 (3)
C2—C3—C4—C51.5 (2)O2—C8—C9—C10−108.21 (16)
C2—C3—C4—N1−179.19 (14)O1—C8—C9—C1071.74 (16)
C3—C4—C5—C6−1.0 (2)C8—C9—C10—O3174.53 (12)
N1—C4—C5—C6179.70 (14)C8—C9—C10—O4−5.34 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O4i0.821.722.5353 (15)175
N1—H1A···O2ii0.911.942.8377 (17)167
N1—H1B···O3iii0.911.862.7642 (17)171
N1—H1C···O1iv0.912.212.8600 (17)128
N1—H1C···O3v0.912.322.9872 (17)130
N1—H1C···O4iv0.912.412.9655 (17)120
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x, −y+1/2, z+1/2; (iii) x, −y+3/2, z+1/2; (iv) −x+2, −y+1, −z+1; (v) x, y−1, z.

Experimental details

Crystal data
Chemical formulaC7H10N+·C3H3O4−
Mr211.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)123
a, b, c (Å)12.7937 (19), 9.2742 (16), 8.5194 (17)
β (°) 104.853 (2)
V (Å3)977.1 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.10 × 0.05 × 0.05
Data collection
DiffractometerRigaku Mercury2
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.910, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		7787, 2228, 1943
Rint0.031
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.111, 1.08
No. of reflections2228
No. of parameters138
No. of restraints4
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.28, −0.24

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O4i0.821.722.5353 (15)174.7
N1—H1A···O2ii0.911.942.8377 (17)166.6
N1—H1B···O3iii0.911.862.7642 (17)171.3
N1—H1C···O1iv0.912.212.8600 (17)127.9
N1—H1C···O3v0.912.322.9872 (17)130.0
N1—H1C···O4iv0.912.412.9655 (17)119.6
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x, −y+1/2, z+1/2; (iii) x, −y+3/2, z+1/2; (iv) −x+2, −y+1, −z+1; (v) x, y−1, z.
 

Acknowledgements

This work was supported by a start-up grant from Southeast University, People's Republic of China.

References

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o1984
https://doi.org/10.1107/S1600536812024403
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