4-Methyl­anilinium 2-carboxyacetate

In the crystal of the title salt, C₇H₁₀N⁺·C₃H₃O₄⁻, the cations are linked to the anions via N—H...O and trifurcated N—H...(O,O,O) hydrogen bonds. The anions are linked into [010] chains by O—H...O hydrogen bonds. Taken together, these interactions generate (100) sheets.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.112
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         C6 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C1 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C4 Check
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.4 Note
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C1       -C6              1.37 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -2.674 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          3 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C3 H3 O4
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        45% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXT2016 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015) and PLATON (Spek, 2009).

4-Methylanilinium 2-carboxyacetate

Crystal data

C7H10N^+·C3H3O4^−	F(000) = 448
Mr = 211.21	Dx = 1.393 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.996 (3) Å	Cell parameters from 2586 reflections
b = 9.2813 (19) Å	θ = 2.7–27.1°
c = 8.665 (2) Å	µ = 0.11 mm^−1
β = 105.503 (7)°	T = 295 K
V = 1007.1 (4) Å^3	Block, colourless
Z = 4	0.24 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	1282 reflections with I > 2σ(I)
ω and φ scan	Rint = 0.031
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θmax = 25.0°, θmin = 2.7°
Tmin = 0.678, Tmax = 0.746	h = −15→15
7352 measured reflections	k = −11→10
1766 independent reflections	l = −10→10

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0494P)^2 + 0.3929P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1766 reflections	Δρmax = 0.21 e Å^−3
141 parameters	Δρmin = −0.19 e Å^−3

Special details

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. All H atoms were located in a difference map. The coordinates of the H atom bonded to O were refined with U(H) set to 1.5U_eq(O). H atoms bonded to C and N were refined using a riding model with U(H) set to 1.2U_eq(C) for the methylene group and 1.5U_eq(C,N) for the methyl and the NH₃ group. Both of them were allowed to rotate but not to tip.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.02784 (18)	0.2864 (3)	0.8804 (3)	0.0459 (6)
C2	0.05733 (19)	0.1495 (3)	0.9312 (3)	0.0575 (8)
H2	0.009107	0.074666	0.896510	0.069*
C3	0.15679 (18)	0.1185 (2)	1.0327 (3)	0.0526 (7)
H3	0.174453	0.024333	1.065946	0.063*
C4	0.22828 (15)	0.2265 (2)	1.0833 (2)	0.0279 (5)
C5	0.20331 (19)	0.3638 (2)	1.0313 (3)	0.0527 (7)
H5	0.252962	0.437536	1.063048	0.063*
C6	0.1029 (2)	0.3927 (3)	0.9305 (3)	0.0654 (9)
H6	0.085992	0.486688	0.895849	0.078*
C7	−0.0826 (2)	0.3149 (3)	0.7724 (4)	0.0721 (9)
H7A	−0.083796	0.293072	0.663661	0.108*
H7B	−0.100685	0.414418	0.780352	0.108*
H7C	−0.133570	0.255254	0.804694	0.108*
C8	0.40281 (15)	−0.05466 (19)	0.8494 (2)	0.0235 (5)
C9	0.38105 (16)	−0.1849 (2)	0.9427 (2)	0.0268 (5)
H9A	0.424395	−0.176610	1.052432	0.032*
H9B	0.306807	−0.182213	0.944691	0.032*
C10	0.40283 (16)	−0.32853 (19)	0.8784 (2)	0.0253 (5)
N1	0.33326 (13)	0.19495 (17)	1.1900 (2)	0.0309 (4)
H1A	0.331546	0.109900	1.236679	0.046*
H1B	0.350879	0.263146	1.264632	0.046*
H1C	0.381413	0.192567	1.133796	0.046*
O1	0.37677 (11)	0.06550 (14)	0.89126 (17)	0.0345 (4)
O2	0.44594 (12)	−0.07617 (13)	0.73668 (17)	0.0327 (4)
O3	0.50449 (11)	−0.35675 (14)	0.90227 (17)	0.0325 (4)
H3A	0.5173 (18)	−0.4328 (17)	0.852 (2)	0.049*
O4	0.33156 (11)	−0.41000 (15)	0.81073 (19)	0.0395 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0363 (13)	0.0460 (14)	0.0477 (15)	0.0015 (11)	−0.0024 (11)	0.0024 (11)
C2	0.0397 (14)	0.0407 (15)	0.080 (2)	−0.0133 (11)	−0.0052 (14)	0.0067 (13)
C3	0.0361 (13)	0.0300 (12)	0.081 (2)	−0.0041 (10)	−0.0025 (13)	0.0090 (12)
C4	0.0252 (11)	0.0264 (11)	0.0320 (11)	0.0024 (8)	0.0073 (9)	0.0001 (9)
C5	0.0493 (15)	0.0311 (13)	0.0623 (17)	−0.0078 (11)	−0.0119 (13)	0.0033 (12)
C6	0.0616 (17)	0.0336 (14)	0.078 (2)	0.0027 (12)	−0.0207 (16)	0.0105 (13)
C7	0.0498 (17)	0.0668 (19)	0.081 (2)	0.0030 (14)	−0.0155 (16)	0.0079 (16)
C8	0.0224 (10)	0.0206 (10)	0.0247 (10)	−0.0008 (8)	0.0011 (9)	−0.0013 (8)
C9	0.0299 (11)	0.0232 (10)	0.0291 (11)	0.0002 (8)	0.0111 (9)	−0.0007 (8)
C10	0.0309 (11)	0.0205 (10)	0.0255 (11)	−0.0024 (9)	0.0094 (9)	0.0054 (8)
N1	0.0274 (9)	0.0244 (9)	0.0410 (11)	−0.0006 (7)	0.0090 (8)	0.0020 (8)
O1	0.0441 (9)	0.0204 (7)	0.0398 (9)	0.0065 (6)	0.0122 (7)	−0.0011 (6)
O2	0.0465 (9)	0.0232 (7)	0.0331 (8)	−0.0009 (6)	0.0187 (7)	0.0001 (6)
O3	0.0338 (8)	0.0205 (7)	0.0441 (9)	−0.0009 (6)	0.0121 (7)	−0.0032 (6)
O4	0.0361 (9)	0.0257 (8)	0.0530 (10)	−0.0061 (7)	0.0056 (8)	−0.0073 (7)

Geometric parameters (Å, º)

C1—C2	1.366 (3)	C7—H7C	0.9600
C1—C6	1.373 (3)	C8—O1	1.247 (2)
C1—C7	1.513 (3)	C8—O2	1.265 (2)
C2—C3	1.385 (3)	C8—C9	1.522 (3)
C2—H2	0.9300	C9—C10	1.501 (3)
C3—C4	1.357 (3)	C9—H9A	0.9700
C3—H3	0.9300	C9—H9B	0.9700
C4—C5	1.362 (3)	C10—O4	1.218 (2)
C4—N1	1.459 (2)	C10—O3	1.308 (2)
C5—C6	1.389 (3)	N1—H1A	0.8900
C5—H5	0.9300	N1—H1B	0.8900
C6—H6	0.9300	N1—H1C	0.8900
C7—H7A	0.9600	O3—H3A	0.868 (10)
C7—H7B	0.9600
C2—C1—C6	116.8 (2)	H7A—C7—H7C	109.5
C2—C1—C7	120.0 (2)	H7B—C7—H7C	109.5
C6—C1—C7	123.1 (2)	O1—C8—O2	125.19 (18)
C1—C2—C3	122.1 (2)	O1—C8—C9	116.89 (18)
C1—C2—H2	118.9	O2—C8—C9	117.92 (16)
C3—C2—H2	118.9	C10—C9—C8	115.34 (16)
C4—C3—C2	119.6 (2)	C10—C9—H9A	108.4
C4—C3—H3	120.2	C8—C9—H9A	108.4
C2—C3—H3	120.2	C10—C9—H9B	108.4
C3—C4—C5	120.2 (2)	C8—C9—H9B	108.4
C3—C4—N1	120.01 (18)	H9A—C9—H9B	107.5
C5—C4—N1	119.81 (18)	O4—C10—O3	123.91 (18)
C4—C5—C6	119.3 (2)	O4—C10—C9	122.39 (18)
C4—C5—H5	120.4	O3—C10—C9	113.70 (16)
C6—C5—H5	120.4	C4—N1—H1A	109.5
C1—C6—C5	122.0 (2)	C4—N1—H1B	109.5
C1—C6—H6	119.0	H1A—N1—H1B	109.5
C5—C6—H6	119.0	C4—N1—H1C	109.5
C1—C7—H7A	109.5	H1A—N1—H1C	109.5
C1—C7—H7B	109.5	H1B—N1—H1C	109.5
H7A—C7—H7B	109.5	C10—O3—H3A	113.8 (16)
C1—C7—H7C	109.5
C6—C1—C2—C3	2.1 (4)	C2—C1—C6—C5	−1.6 (5)
C7—C1—C2—C3	−178.7 (3)	C7—C1—C6—C5	179.2 (3)
C1—C2—C3—C4	−0.5 (5)	C4—C5—C6—C1	−0.4 (5)
C2—C3—C4—C5	−1.6 (4)	O1—C8—C9—C10	173.92 (16)
C2—C3—C4—N1	−179.9 (2)	O2—C8—C9—C10	−6.4 (2)
C3—C4—C5—C6	2.1 (4)	C8—C9—C10—O4	−107.8 (2)
N1—C4—C5—C6	−179.6 (2)	C8—C9—C10—O3	72.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4^i	0.89	1.96	2.846 (2)	172
N1—H1B···O1^ii	0.89	1.91	2.789 (2)	169
N1—H1C···O1	0.89	2.40	3.041 (2)	130
N1—H1C···O2^iii	0.89	2.47	2.980 (2)	117
N1—H1C···O3^iii	0.89	2.21	2.871 (2)	131
O3—H3A···O2^iv	0.87 (1)	1.67 (1)	2.5350 (19)	175 (2)

Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y, −z+2; (iv) −x+1, y−1/2, −z+3/2.