Glycine-phthalic acid (1/1).

In the title compound, C2H5NO2·C8H6O4, the glycine mol-ecule exists as a zwitterion (2-aza-niumyl-ethano-ate) with a positively charged amino group and a negatively charged carboxyl-ate group. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds link the components into layers parallel to the ab plane. The central part of each layer is composed of hydrogen-bonded glycine zwitterions, while phthalic acid mol-ecules inter-act with the zwitterions in such a way that benzene rings protrude up and down from the layer.

Related literature

For related structures, see: Losev et al. (2011 ▶); Herbstein et al. (1981 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶). For head-to-tail hydrogen bonds, see: Sharma et al. (2006 ▶); Selvaraj et al. (2007 ▶).

Experimental

Crystal data

C2H5NO2·C8H6O4

M = 241.20

Orthorhombic,

a = 7.9657 (5) Å

b = 11.3470 (7) Å

c = 23.513 (2) Å

V = 2125.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.13 mm−1

T = 173 K

0.53 × 0.46 × 0.30 mm

Data collection

Stoe IPDS diffractometer

15716 measured reflections

2077 independent reflections

1597 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.090

S = 1.01

2077 reflections

175 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: EXPOSE in IPDS-I Software (Stoe & Cie, 2000 ▶); cell refinement: CELL in IPDS-I Software; data reduction: INTEGRATE in IPDS-I Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681204977X/cv5360sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204977X/cv5360Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204977X/cv5360Isup3.cml

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

C2H5NO2·C8H6O4	F(000) = 1008
Mr = 241.20	Dx = 1.508 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8000 reflections
a = 7.9657 (5) Å	θ = 2.6–26.1°
b = 11.3470 (7) Å	µ = 0.13 mm−1
c = 23.513 (2) Å	T = 173 K
V = 2125.3 (3) Å3	Block, colourless
Z = 8	0.53 × 0.46 × 0.30 mm

Stoe IPDS diffractometer	1597 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.041
Graphite monochromator	θmax = 26.0°, θmin = 3.1°
Detector resolution: 0.81Å pixels mm-1	h = −9→9
phi rotation scans	k = −13→13
15716 measured reflections	l = −29→28
2077 independent reflections

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.064P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2077 reflections	Δρmax = 0.22 e Å−3
175 parameters	Δρmin = −0.19 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: 0.0086 (15)

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
O3	−0.06389 (12)	0.23293 (9)	0.08480 (4)	0.0293 (3)
O4	−0.00401 (15)	0.40181 (9)	0.12875 (4)	0.0374 (3)
H4O	−0.058 (3)	0.435 (2)	0.0959 (11)	0.075 (7)*
O5	0.00354 (13)	−0.05643 (9)	0.12213 (4)	0.0365 (3)
O6	0.19779 (12)	0.05907 (9)	0.08314 (4)	0.0311 (3)
H6O	0.205 (3)	−0.008 (2)	0.0572 (10)	0.072 (6)*
C3	0.06342 (15)	0.22668 (12)	0.17621 (5)	0.0238 (3)
C4	0.10175 (15)	0.10660 (12)	0.17542 (5)	0.0242 (3)
C5	0.15369 (17)	0.05214 (13)	0.22514 (6)	0.0294 (3)
H5	0.1795	−0.0296	0.2247	0.035*
C6	0.16855 (19)	0.11483 (14)	0.27541 (6)	0.0347 (3)
H6	0.2054	0.0764	0.3091	0.042*
C7	0.12967 (18)	0.23317 (14)	0.27639 (6)	0.0336 (3)
H7	0.1387	0.2765	0.3108	0.040*
C8	0.07751 (17)	0.28854 (13)	0.22713 (6)	0.0278 (3)
H8	0.0508	0.3701	0.2280	0.033*
C9	−0.00603 (16)	0.28671 (12)	0.12521 (5)	0.0249 (3)
C10	0.09312 (16)	0.03014 (11)	0.12370 (5)	0.0247 (3)
O1	0.75187 (11)	0.11587 (8)	−0.01838 (4)	0.0269 (2)
O2	0.65409 (12)	−0.01881 (8)	0.04157 (4)	0.0317 (3)
N1	0.59761 (16)	0.29647 (10)	0.03063 (5)	0.0258 (3)
H1A	0.543 (2)	0.3538 (16)	0.0511 (8)	0.042 (5)*
H1B	0.560 (2)	0.2998 (17)	−0.0061 (9)	0.051 (5)*
H1C	0.704 (3)	0.3178 (16)	0.0329 (8)	0.043 (5)*
C1	0.66689 (15)	0.08474 (11)	0.02398 (5)	0.0226 (3)
C2	0.57097 (16)	0.17890 (11)	0.05551 (6)	0.0249 (3)
H2A	0.4497	0.1599	0.0546	0.030*
H2B	0.6072	0.1798	0.0958	0.030*

	U11	U22	U33	U12	U13	U23
O3	0.0348 (5)	0.0245 (5)	0.0286 (5)	−0.0013 (4)	−0.0052 (4)	−0.0042 (4)
O4	0.0615 (7)	0.0201 (6)	0.0307 (6)	−0.0003 (5)	−0.0090 (5)	−0.0012 (4)
O5	0.0476 (6)	0.0296 (6)	0.0322 (6)	−0.0152 (5)	0.0070 (4)	−0.0067 (4)
O6	0.0368 (5)	0.0226 (5)	0.0338 (5)	−0.0036 (4)	0.0124 (4)	−0.0055 (4)
C3	0.0231 (6)	0.0230 (7)	0.0251 (7)	−0.0023 (5)	0.0022 (5)	−0.0020 (5)
C4	0.0215 (6)	0.0229 (7)	0.0280 (7)	−0.0032 (5)	0.0035 (5)	−0.0018 (5)
C5	0.0318 (7)	0.0250 (7)	0.0315 (7)	0.0004 (6)	0.0006 (5)	0.0024 (6)
C6	0.0398 (8)	0.0363 (9)	0.0279 (7)	−0.0013 (6)	−0.0036 (6)	0.0047 (6)
C7	0.0408 (8)	0.0355 (9)	0.0245 (7)	−0.0047 (7)	−0.0017 (6)	−0.0044 (6)
C8	0.0313 (7)	0.0239 (7)	0.0283 (7)	−0.0016 (5)	0.0009 (5)	−0.0055 (5)
C9	0.0269 (6)	0.0213 (7)	0.0266 (7)	−0.0011 (5)	0.0014 (5)	−0.0026 (5)
C10	0.0278 (6)	0.0186 (7)	0.0277 (7)	−0.0001 (5)	0.0021 (5)	−0.0004 (5)
O1	0.0323 (5)	0.0227 (5)	0.0256 (5)	−0.0013 (4)	0.0069 (4)	−0.0038 (4)
O2	0.0415 (6)	0.0204 (5)	0.0332 (5)	0.0037 (4)	0.0057 (4)	0.0041 (4)
N1	0.0293 (6)	0.0192 (6)	0.0288 (6)	0.0010 (5)	0.0024 (5)	−0.0043 (5)
C1	0.0244 (6)	0.0211 (7)	0.0223 (6)	−0.0002 (5)	−0.0017 (5)	−0.0016 (5)
C2	0.0283 (7)	0.0216 (7)	0.0247 (6)	−0.0002 (5)	0.0040 (5)	−0.0012 (5)

O3—C9	1.2197 (15)	C6—H6	0.9500
O4—C9	1.3088 (18)	C7—C8	1.382 (2)
O4—H4O	0.96 (3)	C7—H7	0.9500
O5—C10	1.2147 (16)	C8—H8	0.9500
O6—C10	1.3086 (16)	O1—C1	1.2550 (15)
O6—H6O	0.98 (2)	O2—C1	1.2498 (16)
C3—C8	1.3925 (18)	N1—C2	1.4720 (17)
C3—C4	1.396 (2)	N1—H1A	0.917 (19)
C3—C9	1.4859 (18)	N1—H1B	0.91 (2)
C4—C5	1.3855 (19)	N1—H1C	0.88 (2)
C4—C10	1.4955 (18)	C1—C2	1.5083 (18)
C5—C6	1.385 (2)	C2—H2A	0.9900
C5—H5	0.9500	C2—H2B	0.9900
C6—C7	1.378 (2)
C9—O4—H4O	109.8 (14)	O3—C9—C3	122.68 (13)
C10—O6—H6O	107.5 (13)	O4—C9—C3	113.67 (11)
C8—C3—C4	119.06 (12)	O5—C10—O6	123.72 (12)
C8—C3—C9	119.52 (12)	O5—C10—C4	121.39 (11)
C4—C3—C9	121.20 (11)	O6—C10—C4	114.70 (11)
C5—C4—C3	119.29 (12)	C2—N1—H1A	111.5 (11)
C5—C4—C10	116.18 (12)	C2—N1—H1B	111.5 (12)
C3—C4—C10	124.53 (12)	H1A—N1—H1B	108.2 (16)
C6—C5—C4	121.11 (13)	C2—N1—H1C	111.3 (12)
C6—C5—H5	119.4	H1A—N1—H1C	103.1 (16)
C4—C5—H5	119.4	H1B—N1—H1C	110.9 (17)
C7—C6—C5	119.71 (13)	O2—C1—O1	124.83 (12)
C7—C6—H6	120.1	O2—C1—C2	117.52 (11)
C5—C6—H6	120.1	O1—C1—C2	117.64 (11)
C6—C7—C8	119.78 (13)	N1—C2—C1	111.94 (11)
C6—C7—H7	120.1	N1—C2—H2A	109.2
C8—C7—H7	120.1	C1—C2—H2A	109.2
C7—C8—C3	121.05 (13)	N1—C2—H2B	109.2
C7—C8—H8	119.5	C1—C2—H2B	109.2
C3—C8—H8	119.5	H2A—C2—H2B	107.9
O3—C9—O4	123.61 (13)
C8—C3—C4—C5	−0.36 (18)	C8—C3—C9—O3	−159.60 (13)
C9—C3—C4—C5	−174.93 (12)	C4—C3—C9—O3	14.95 (19)
C8—C3—C4—C10	−179.55 (12)	C8—C3—C9—O4	18.29 (17)
C9—C3—C4—C10	5.88 (19)	C4—C3—C9—O4	−167.16 (12)
C3—C4—C5—C6	−0.2 (2)	C5—C4—C10—O5	59.45 (18)
C10—C4—C5—C6	179.09 (12)	C3—C4—C10—O5	−121.34 (15)
C4—C5—C6—C7	0.6 (2)	C5—C4—C10—O6	−115.59 (13)
C5—C6—C7—C8	−0.5 (2)	C3—C4—C10—O6	63.62 (17)
C6—C7—C8—C3	0.0 (2)	O2—C1—C2—N1	179.74 (11)
C4—C3—C8—C7	0.46 (19)	O1—C1—C2—N1	−1.15 (17)
C9—C3—C8—C7	175.12 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5i	0.917 (19)	1.992 (19)	2.8398 (16)	153.0 (16)
N1—H1B···O3ii	0.91 (2)	2.13 (2)	3.0219 (16)	164.6 (17)
N1—H1C···O2iii	0.88 (2)	2.181 (19)	2.8934 (16)	137.4 (15)
N1—H1C···O3iv	0.88 (2)	2.416 (19)	3.0681 (16)	130.9 (15)
O4—H4O···O2i	0.96 (3)	1.58 (3)	2.5383 (14)	175 (2)
O6—H6O···O1v	0.98 (2)	1.56 (2)	2.5337 (13)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5i	0.917 (19)	1.992 (19)	2.8398 (16)	153.0 (16)
N1—H1B⋯O3ii	0.91 (2)	2.13 (2)	3.0219 (16)	164.6 (17)
N1—H1C⋯O2iii	0.88 (2)	2.181 (19)	2.8934 (16)	137.4 (15)
N1—H1C⋯O3iv	0.88 (2)	2.416 (19)	3.0681 (16)	130.9 (15)
O4—H4O⋯O2i	0.96 (3)	1.58 (3)	2.5383 (14)	175 (2)
O6—H6O⋯O1v	0.98 (2)	1.56 (2)	2.5337 (13)	171 (2)

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