Crystal structure of 2-phenyl-ethanaminium 3-carb-oxy-prop-2-enoate.

The title mol-ecular salt, C8H12N(+)·C4H3O4 (-), crystallized with two independent cations and anions in the asymmetric unit. The ethanaminium side chains of the cations exhibit anti conformations [C-C-C-N torsion angles = 176.5 (3) and -179.4 (3)°]. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds connect adjacent anions and cations, and , O-H⋯O hydrogen bonds connect adjacent anions, generating sheets parallel to (001).

Related literature

For the crystal structures of related compounds, see: Ambalatharasu et al. (2014 ▸); Lejon et al. (2006 ▸); Smith et al. (2003 ▸).

Experimental

Crystal data

C8H12N+·C4H3O4 −

M = 237.25

Triclinic,

a = 9.2940 (5) Å

b = 10.8010 (7) Å

c = 12.7470 (8) Å

α = 81.773 (4)°

β = 88.907 (5)°

γ = 87.396 (4)°

V = 1265.02 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.26 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.976, T max = 0.982

29606 measured reflections

5579 independent reflections

3453 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.199

S = 1.04

5579 reflections

309 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015014292/su5183sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014292/su5183Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015014292/su5183Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015014292/su5183fig1.tif

The mol­ecular structure of the title salt, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015014292/su5183fig2.tif

The crystal packing of the title salt viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 1) and C-bound H atoms have been omitted for clarity.

CCDC reference: 1415628

Additional supporting information: crystallographic information; 3D view; checkCIF report

C8H12N+·C4H3O4−	Z = 4
Mr = 237.25	F(000) = 504
Triclinic, P1	Dx = 1.246 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2940 (5) Å	Cell parameters from 7705 reflections
b = 10.8010 (7) Å	θ = 2.2–27.1°
c = 12.7470 (8) Å	µ = 0.09 mm−1
α = 81.773 (4)°	T = 295 K
β = 88.907 (5)°	Block, colourless
γ = 87.396 (4)°	0.26 × 0.24 × 0.20 mm
V = 1265.02 (13) Å3

Bruker Kappa APEXII CCD diffractometer	5579 independent reflections
Radiation source: fine-focus sealed tube	3453 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ω and φ scan	θmax = 27.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.976, Tmax = 0.982	k = −13→13
29606 measured reflections	l = −16→16

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.199	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0955P)2 + 0.6291P] where P = (Fo2 + 2Fc2)/3
5579 reflections	(Δ/σ)max < 0.001
309 parameters	Δρmax = 0.39 e Å−3
3 restraints	Δρmin = −0.28 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
C1	0.3953 (4)	0.2508 (4)	−0.0808 (3)	0.0901 (13)
C2	0.3882 (6)	0.1650 (6)	0.0060 (4)	0.1224 (18)
H2	0.3988	0.0810	−0.0024	0.147*
C3	0.3664 (7)	0.1939 (8)	0.1061 (4)	0.159 (3)
H3	0.3691	0.1307	0.1639	0.191*
C4	0.3403 (8)	0.3176 (9)	0.1216 (5)	0.175 (4)
H4	0.3165	0.3389	0.1881	0.210*
C5	0.3508 (11)	0.4049 (10)	0.0362 (5)	0.214 (4)
H5	0.3414	0.4888	0.0453	0.257*
C6	0.3750 (9)	0.3752 (5)	−0.0654 (4)	0.175 (3)
H6	0.3777	0.4386	−0.1230	0.210*
C7	0.4238 (4)	0.2131 (5)	−0.1903 (3)	0.0956 (14)
H7A	0.4901	0.2704	−0.2290	0.115*
H7B	0.4695	0.1299	−0.1824	0.115*
C8	0.2922 (3)	0.2139 (3)	−0.2520 (2)	0.0587 (8)
H8A	0.2434	0.2957	−0.2558	0.070*
H8B	0.2285	0.1529	−0.2152	0.070*
C9	−0.0810 (4)	0.2157 (3)	0.0186 (3)	0.0697 (9)
C10	−0.0453 (7)	0.3273 (4)	−0.0371 (4)	0.1176 (18)
H10	−0.0028	0.3866	−0.0030	0.141*
C11	−0.0731 (8)	0.3531 (5)	−0.1475 (4)	0.142 (2)
H11	−0.0477	0.4290	−0.1859	0.171*
C12	−0.1362 (7)	0.2677 (6)	−0.1965 (4)	0.124 (2)
H12	−0.1611	0.2872	−0.2674	0.149*
C13	−0.1632 (6)	0.1557 (6)	−0.1439 (4)	0.1197 (19)
H13	−0.1986	0.0946	−0.1798	0.144*
C14	−0.1388 (5)	0.1290 (4)	−0.0354 (3)	0.0941 (13)
H14	−0.1619	0.0514	0.0009	0.113*
C15	−0.0560 (4)	0.1892 (4)	0.1377 (3)	0.0710 (9)
H15A	−0.0280	0.1014	0.1571	0.085*
H15B	0.0224	0.2383	0.1556	0.085*
C16	−0.1874 (3)	0.2197 (3)	0.1996 (2)	0.0553 (7)
H16A	−0.2159	0.3073	0.1793	0.066*
H16B	−0.2654	0.1700	0.1819	0.066*
C17	0.9242 (2)	0.0767 (2)	−0.40812 (17)	0.0297 (5)
C18	0.8125 (2)	−0.0199 (2)	−0.39499 (18)	0.0323 (5)
H18	0.8431	−0.1039	−0.3845	0.039*
C19	0.6736 (2)	0.0079 (2)	−0.39746 (18)	0.0314 (5)
H19	0.6431	0.0919	−0.4074	0.038*
C20	0.5617 (2)	−0.0890 (2)	−0.38511 (17)	0.0312 (5)
C21	0.8888 (2)	−0.3850 (2)	−0.43107 (19)	0.0347 (5)
C22	0.7711 (2)	−0.4760 (2)	−0.42610 (19)	0.0365 (5)
H22	0.7233	−0.4982	−0.3619	0.044*
C23	0.7326 (2)	−0.5258 (2)	−0.5096 (2)	0.0352 (5)
H23	0.7801	−0.5022	−0.5737	0.042*
C24	0.6170 (2)	−0.61804 (19)	−0.50667 (19)	0.0336 (5)
N1	0.3190 (2)	0.1850 (2)	−0.36129 (16)	0.0433 (5)
H1A	0.3817	0.2375	−0.3943	0.065*
H1B	0.2366	0.1933	−0.3966	0.065*
H1C	0.3547	0.1067	−0.3585	0.065*
N2	−0.1646 (2)	0.1957 (2)	0.31577 (16)	0.0439 (5)
H2A	−0.1254	0.1189	0.3334	0.066*
H2B	−0.2488	0.2021	0.3495	0.066*
H2C	−0.1058	0.2515	0.3341	0.066*
O1	1.04844 (16)	0.04879 (15)	−0.37585 (14)	0.0410 (4)
O2	0.88262 (16)	0.18467 (14)	−0.45441 (13)	0.0388 (4)
H2D	0.9498	0.2318	−0.4584	0.058*
O3	0.60245 (17)	−0.19778 (15)	−0.40468 (15)	0.0428 (4)
O4	0.43731 (16)	−0.05906 (15)	−0.35813 (15)	0.0436 (4)
O5	0.92154 (17)	−0.33377 (15)	−0.52644 (14)	0.0421 (4)
O6	0.9469 (2)	−0.36439 (18)	−0.34987 (15)	0.0531 (5)
O7	0.59639 (17)	−0.65424 (16)	−0.59847 (14)	0.0446 (4)
H7	0.5322	−0.7045	−0.5928	0.067*
O8	0.54969 (18)	−0.65294 (16)	−0.42533 (14)	0.0459 (5)

	U11	U22	U33	U12	U13	U23
C1	0.093 (3)	0.133 (4)	0.049 (2)	−0.040 (3)	0.0008 (18)	−0.020 (2)
C2	0.131 (4)	0.163 (5)	0.068 (3)	0.013 (4)	−0.012 (3)	−0.005 (3)
C3	0.155 (6)	0.270 (10)	0.044 (3)	−0.002 (6)	−0.010 (3)	0.007 (4)
C4	0.144 (5)	0.322 (13)	0.080 (4)	−0.031 (7)	0.014 (4)	−0.098 (6)
C5	0.302 (11)	0.240 (10)	0.131 (6)	−0.054 (8)	0.012 (7)	−0.116 (7)
C6	0.287 (10)	0.155 (6)	0.094 (4)	−0.065 (6)	−0.012 (5)	−0.041 (4)
C7	0.070 (2)	0.161 (4)	0.061 (2)	−0.027 (3)	−0.0009 (18)	−0.029 (2)
C8	0.0557 (17)	0.076 (2)	0.0464 (17)	−0.0103 (15)	0.0040 (13)	−0.0135 (14)
C9	0.082 (2)	0.080 (2)	0.0449 (18)	0.0080 (19)	0.0043 (16)	−0.0078 (17)
C10	0.197 (6)	0.087 (3)	0.068 (3)	−0.021 (3)	0.015 (3)	−0.005 (2)
C11	0.242 (7)	0.099 (4)	0.073 (3)	0.021 (4)	0.035 (4)	0.017 (3)
C12	0.183 (6)	0.136 (5)	0.047 (2)	0.078 (4)	−0.006 (3)	−0.014 (3)
C13	0.154 (5)	0.143 (5)	0.070 (3)	0.037 (4)	−0.025 (3)	−0.049 (3)
C14	0.125 (4)	0.098 (3)	0.062 (2)	−0.003 (3)	−0.005 (2)	−0.021 (2)
C15	0.064 (2)	0.096 (3)	0.0515 (19)	0.0026 (18)	0.0002 (15)	−0.0069 (18)
C16	0.0506 (16)	0.074 (2)	0.0401 (15)	−0.0053 (14)	−0.0039 (12)	−0.0041 (14)
C17	0.0272 (11)	0.0323 (11)	0.0316 (12)	−0.0103 (9)	0.0020 (9)	−0.0085 (9)
C18	0.0310 (11)	0.0294 (11)	0.0374 (13)	−0.0104 (9)	−0.0003 (9)	−0.0054 (9)
C19	0.0292 (11)	0.0284 (11)	0.0375 (12)	−0.0084 (9)	−0.0008 (9)	−0.0050 (9)
C20	0.0271 (11)	0.0356 (12)	0.0320 (12)	−0.0116 (9)	−0.0032 (9)	−0.0046 (9)
C21	0.0315 (11)	0.0289 (11)	0.0441 (14)	−0.0078 (9)	−0.0032 (10)	−0.0042 (10)
C22	0.0335 (12)	0.0340 (12)	0.0419 (13)	−0.0116 (9)	0.0010 (10)	−0.0016 (10)
C23	0.0286 (11)	0.0304 (11)	0.0472 (14)	−0.0102 (9)	0.0034 (10)	−0.0049 (10)
C24	0.0279 (11)	0.0275 (11)	0.0467 (14)	−0.0069 (9)	−0.0003 (10)	−0.0075 (10)
N1	0.0332 (10)	0.0536 (13)	0.0438 (12)	−0.0058 (9)	−0.0007 (9)	−0.0078 (10)
N2	0.0374 (11)	0.0566 (13)	0.0385 (12)	−0.0057 (10)	−0.0005 (9)	−0.0087 (10)
O1	0.0283 (8)	0.0406 (9)	0.0546 (11)	−0.0102 (7)	−0.0051 (7)	−0.0052 (8)
O2	0.0294 (8)	0.0324 (8)	0.0538 (11)	−0.0136 (6)	−0.0033 (7)	0.0006 (7)
O3	0.0306 (8)	0.0359 (9)	0.0656 (12)	−0.0113 (7)	0.0020 (8)	−0.0169 (8)
O4	0.0277 (8)	0.0411 (9)	0.0630 (12)	−0.0097 (7)	0.0057 (7)	−0.0088 (8)
O5	0.0384 (9)	0.0423 (9)	0.0452 (10)	−0.0192 (7)	−0.0041 (7)	0.0014 (8)
O6	0.0586 (11)	0.0563 (11)	0.0474 (11)	−0.0278 (9)	−0.0094 (9)	−0.0081 (9)
O7	0.0358 (9)	0.0456 (10)	0.0569 (11)	−0.0192 (7)	0.0046 (8)	−0.0177 (8)
O8	0.0420 (10)	0.0457 (10)	0.0510 (11)	−0.0205 (8)	0.0058 (8)	−0.0055 (8)

C1—C2	1.341 (6)	C15—H15A	0.9700
C1—C6	1.3894 (10)	C15—H15B	0.9700
C1—C7	1.524 (5)	C16—N2	1.484 (3)
C2—C3	1.366 (8)	C16—H16A	0.9700
C2—H2	0.9300	C16—H16B	0.9700
C3—C4	1.3888 (10)	C17—O1	1.243 (3)
C3—H3	0.9300	C17—O2	1.276 (3)
C4—C5	1.339 (11)	C17—C18	1.496 (3)
C4—H4	0.9300	C18—C19	1.312 (3)
C5—C6	1.3902 (10)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.499 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.465 (5)	C20—O4	1.242 (3)
C7—H7A	0.9700	C20—O3	1.276 (3)
C7—H7B	0.9700	C21—O6	1.229 (3)
C8—N1	1.485 (4)	C21—O5	1.298 (3)
C8—H8A	0.9700	C21—C22	1.498 (3)
C8—H8B	0.9700	C22—C23	1.322 (3)
C9—C10	1.360 (6)	C22—H22	0.9300
C9—C14	1.373 (5)	C23—C24	1.495 (3)
C9—C15	1.524 (4)	C23—H23	0.9300
C10—C11	1.421 (7)	C24—O8	1.222 (3)
C10—H10	0.9300	C24—O7	1.306 (3)
C11—C12	1.347 (8)	N1—H1A	0.8900
C11—H11	0.9300	N1—H1B	0.8900
C12—C13	1.329 (8)	N1—H1C	0.8900
C12—H12	0.9300	N2—H2A	0.8900
C13—C14	1.393 (6)	N2—H2B	0.8900
C13—H13	0.9300	N2—H2C	0.8900
C14—H14	0.9300	O2—H2D	0.8200
C15—C16	1.491 (4)	O7—H7	0.8200
C2—C1—C6	116.4 (5)	C16—C15—H15A	109.2
C2—C1—C7	121.5 (5)	C9—C15—H15A	109.2
C6—C1—C7	122.1 (4)	C16—C15—H15B	109.2
C1—C2—C3	123.8 (6)	C9—C15—H15B	109.2
C1—C2—H2	118.1	H15A—C15—H15B	107.9
C3—C2—H2	118.1	N2—C16—C15	112.6 (2)
C2—C3—C4	120.0 (6)	N2—C16—H16A	109.1
C2—C3—H3	120.0	C15—C16—H16A	109.1
C4—C3—H3	120.0	N2—C16—H16B	109.1
C5—C4—C3	116.9 (6)	C15—C16—H16B	109.1
C5—C4—H4	121.6	H16A—C16—H16B	107.8
C3—C4—H4	121.6	O1—C17—O2	124.44 (18)
C4—C5—C6	122.7 (8)	O1—C17—C18	119.9 (2)
C4—C5—H5	118.6	O2—C17—C18	115.61 (18)
C6—C5—H5	118.6	C19—C18—C17	123.3 (2)
C1—C6—C5	119.9 (6)	C19—C18—H18	118.4
C1—C6—H6	120.0	C17—C18—H18	118.4
C5—C6—H6	120.0	C18—C19—C20	123.3 (2)
C8—C7—C1	112.8 (3)	C18—C19—H19	118.4
C8—C7—H7A	109.0	C20—C19—H19	118.4
C1—C7—H7A	109.0	O4—C20—O3	124.52 (19)
C8—C7—H7B	109.0	O4—C20—C19	119.1 (2)
C1—C7—H7B	109.0	O3—C20—C19	116.41 (19)
H7A—C7—H7B	107.8	O6—C21—O5	125.11 (19)
C7—C8—N1	113.5 (3)	O6—C21—C22	120.8 (2)
C7—C8—H8A	108.9	O5—C21—C22	114.1 (2)
N1—C8—H8A	108.9	C23—C22—C21	122.5 (2)
C7—C8—H8B	108.9	C23—C22—H22	118.8
N1—C8—H8B	108.9	C21—C22—H22	118.8
H8A—C8—H8B	107.7	C22—C23—C24	123.6 (2)
C10—C9—C14	118.2 (4)	C22—C23—H23	118.2
C10—C9—C15	120.1 (4)	C24—C23—H23	118.2
C14—C9—C15	121.7 (3)	O8—C24—O7	125.07 (19)
C9—C10—C11	119.9 (5)	O8—C24—C23	121.8 (2)
C9—C10—H10	120.0	O7—C24—C23	113.2 (2)
C11—C10—H10	120.0	C8—N1—H1A	109.5
C12—C11—C10	120.0 (5)	C8—N1—H1B	109.5
C12—C11—H11	120.0	H1A—N1—H1B	109.5
C10—C11—H11	120.0	C8—N1—H1C	109.5
C13—C12—C11	120.3 (5)	H1A—N1—H1C	109.5
C13—C12—H12	119.9	H1B—N1—H1C	109.5
C11—C12—H12	119.9	C16—N2—H2A	109.5
C12—C13—C14	120.5 (5)	C16—N2—H2B	109.5
C12—C13—H13	119.8	H2A—N2—H2B	109.5
C14—C13—H13	119.8	C16—N2—H2C	109.5
C9—C14—C13	120.9 (5)	H2A—N2—H2C	109.5
C9—C14—H14	119.6	H2B—N2—H2C	109.5
C13—C14—H14	119.6	C17—O2—H2D	109.5
C16—C15—C9	111.8 (3)	C24—O7—H7	109.5
C6—C1—C2—C3	−1.7 (8)	C10—C9—C14—C13	−1.4 (7)
C7—C1—C2—C3	178.4 (5)	C15—C9—C14—C13	178.9 (4)
C1—C2—C3—C4	4.4 (10)	C12—C13—C14—C9	−2.7 (8)
C2—C3—C4—C5	−5.9 (12)	C10—C9—C15—C16	94.4 (5)
C3—C4—C5—C6	5.1 (14)	C14—C9—C15—C16	−85.9 (4)
C2—C1—C6—C5	0.7 (10)	C9—C15—C16—N2	−179.4 (3)
C7—C1—C6—C5	−179.3 (6)	O1—C17—C18—C19	159.4 (2)
C4—C5—C6—C1	−2.6 (14)	O2—C17—C18—C19	−21.4 (3)
C2—C1—C7—C8	100.0 (5)	C17—C18—C19—C20	179.5 (2)
C6—C1—C7—C8	−79.9 (6)	C18—C19—C20—O4	159.5 (2)
C1—C7—C8—N1	176.5 (3)	C18—C19—C20—O3	−21.2 (3)
C14—C9—C10—C11	2.3 (8)	O6—C21—C22—C23	−161.6 (2)
C15—C9—C10—C11	−178.0 (5)	O5—C21—C22—C23	18.0 (3)
C9—C10—C11—C12	0.8 (9)	C21—C22—C23—C24	179.2 (2)
C10—C11—C12—C13	−4.9 (10)	C22—C23—C24—O8	0.3 (4)
C11—C12—C13—C14	5.9 (9)	C22—C23—C24—O7	179.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O4	0.89	1.92	2.805 (3)	177
N1—H1A···O8i	0.89	2.00	2.863 (3)	163
N1—H1B···O1ii	0.89	2.38	2.992 (2)	126
N1—H1B···O5iii	0.89	2.20	2.961 (3)	143
N2—H2A···O1iv	0.89	1.92	2.814 (3)	177
N2—H2C···O6iv	0.89	1.99	2.863 (3)	167
N2—H2B···O7v	0.89	2.23	2.974 (3)	141
N2—H2B···O4vi	0.89	2.38	2.992 (2)	126
O2—H2D···O5vii	0.82	1.65	2.470 (2)	176
O7—H7···O3viii	0.82	1.68	2.494 (2)	174
C7—H7A···O8i	0.97	2.58	3.349 (4)	136

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1CO4	0.89	1.92	2.805(3)	177
N1H1AO8i	0.89	2.00	2.863(3)	163
N1H1BO1ii	0.89	2.38	2.992(2)	126
N1H1BO5iii	0.89	2.20	2.961(3)	143
N2H2AO1iv	0.89	1.92	2.814(3)	177
N2H2CO6iv	0.89	1.99	2.863(3)	167
N2H2BO7v	0.89	2.23	2.974(3)	141
N2H2BO4vi	0.89	2.38	2.992(2)	126
O2H2DO5vii	0.82	1.65	2.470(2)	176
O7H7O3viii	0.82	1.68	2.494(2)	174
C7H7AO8i	0.97	2.58	3.349(4)	136

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .