(S)-Alanine-(S)-2-phen-oxy-propionic acid (1/1).

In the title co-crystal, C(3)H(7)NO(2)·C(9)H(10)O(3), the (S)-alanine mol-ecule exists in the zwitterionic form stabilized by two pairs of N(+)-H⋯O(-) hydrogen bonds and an electrostatic inter-action between the ammonium center and the carboxyl-ate anion, forming a sheet along the ab plane. The carboxyl group of the (S)-2-phen-oxy-propionic acid mol-ecule is connected to the top and bottom of the sheet via N(+)-H⋯O=C and O-H⋯O(-) [R(2) (2)(7) graph set] hydrogen bonds, giving an (S,S)-homochiral layer, in which both methyl groups of (S)-alanine and the phenyl rings of (S)-2-phen-oxy-propionic acid are oriented in the same direction along the b axis.

Related literature

For the use of a chiral resolution agents, see: Hasegawa et al. (1998 ▶). For the crystal structure of enanti­omeric and racemic 2-phen­oxy­propionic acid, see: Sørensen & Larsen (2003 ▶). For the crystal structure of (S)-alanine–(R)-2-phen­oxy­propionic acid, see: Takahashi & Fujii (2004 ▶).

Experimental

Crystal data

C3H7NO2·C9H10O3

M = 255.27

Monoclinic,

a = 5.227 (5) Å

b = 7.364 (5) Å

c = 17.493 (5) Å

β = 95.232 (5)°

V = 670.5 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.7 × 0.5 × 0.3 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

3872 measured reflections

2742 independent reflections

2698 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.081

S = 1.06

2742 reflections

171 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.13 e Å−3

Absolute structure: Flack (1983 ▶), 930 Friedel pairs

Flack parameter: −0.4 (8)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶) and ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812020727/ds2190sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020727/ds2190Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020727/ds2190Isup3.cml

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

C3H7NO2·C9H10O3	F(000) = 272
Mr = 255.27	Dx = 1.264 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2yb	Cell parameters from 3229 reflections
a = 5.227 (5) Å	θ = 2.3–28.5°
b = 7.364 (5) Å	µ = 0.10 mm−1
c = 17.493 (5) Å	T = 293 K
β = 95.232 (5)°	Plate, colourless
V = 670.5 (8) Å3	0.7 × 0.5 × 0.3 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	2698 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 28.5°, θmin = 2.3°
Detector resolution: 8.333 pixels mm-1	h = −6→5
phi and ω scan	k = −9→9
3872 measured reflections	l = −21→23
2742 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.029	w = 1/[σ2(Fo2) + (0.0452P)2 + 0.0566P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.081	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.17 e Å−3
2742 reflections	Δρmin = −0.13 e Å−3
171 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008)
1 restraint	Extinction coefficient: 0.160 (9)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 930 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.4 (8)

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.

	x	y	z	Uiso*/Ueq
C1	0.2142 (2)	0.91172 (17)	0.27450 (7)	0.0400 (3)
C2	0.2315 (3)	0.9885 (2)	0.19397 (8)	0.0489 (3)
H2	0.4105	1.0177	0.1867	0.059*
C3	0.0685 (5)	1.1604 (3)	0.18625 (12)	0.0785 (6)
H3A	0.0795	1.2125	0.1363	0.118*
H3B	0.1306	1.2461	0.2249	0.118*
H3C	−0.1071	1.1307	0.1926	0.118*
C4	0.2830 (3)	0.7215 (2)	0.12044 (7)	0.0460 (3)
C5	0.5113 (3)	0.6774 (3)	0.16181 (8)	0.0531 (3)
H5	0.5723	0.7466	0.2041	0.064*
C6	0.6486 (4)	0.5288 (3)	0.13974 (10)	0.0688 (5)
H6	0.8015	0.4971	0.168	0.083*
C7	0.5623 (4)	0.4276 (3)	0.07671 (12)	0.0776 (6)
H7	0.6572	0.3286	0.0622	0.093*
C8	0.3355 (4)	0.4726 (3)	0.03498 (10)	0.0708 (5)
H8	0.2773	0.4045	−0.0079	0.085*
C9	0.1955 (3)	0.6180 (2)	0.05671 (8)	0.0572 (4)
H9	0.0412	0.6477	0.0288	0.069*
C10	0.5537 (2)	0.48177 (15)	0.48456 (7)	0.0332 (2)
C11	0.6485 (2)	0.55376 (16)	0.41011 (6)	0.0337 (2)
H11	0.5119	0.6252	0.3823	0.04*
C12	0.7222 (4)	0.3969 (2)	0.35972 (9)	0.0634 (4)
H12A	0.7836	0.4441	0.3136	0.095*
H12B	0.5746	0.3217	0.3468	0.095*
H12C	0.855	0.3261	0.387	0.095*
N1	0.87704 (17)	0.67096 (13)	0.42842 (5)	0.0322 (2)
H1A	1.0014	0.6064	0.4537	0.048*
H1B	0.835	0.7636	0.4574	0.048*
H1C	0.9317	0.7131	0.3851	0.048*
O1	0.3772 (2)	0.98974 (17)	0.32449 (6)	0.0594 (3)
O2	0.0633 (2)	0.79618 (16)	0.28881 (5)	0.0556 (3)
O3	0.1324 (2)	0.86666 (16)	0.13631 (5)	0.0543 (3)
O4	0.72311 (17)	0.45179 (16)	0.53819 (5)	0.0478 (2)
O5	0.32016 (16)	0.45273 (15)	0.48470 (6)	0.0505 (3)
H1O	0.348 (4)	0.961 (4)	0.3808 (13)	0.090 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0455 (6)	0.0409 (6)	0.0347 (5)	−0.0023 (5)	0.0092 (5)	0.0001 (5)
C2	0.0571 (8)	0.0507 (7)	0.0405 (6)	−0.0004 (6)	0.0123 (5)	0.0086 (6)
C3	0.1025 (15)	0.0610 (10)	0.0741 (11)	0.0222 (10)	0.0188 (11)	0.0239 (9)
C4	0.0487 (7)	0.0597 (8)	0.0306 (5)	−0.0026 (6)	0.0090 (5)	0.0051 (5)
C5	0.0523 (8)	0.0688 (9)	0.0387 (6)	0.0046 (7)	0.0064 (5)	−0.0053 (7)
C6	0.0626 (10)	0.0849 (13)	0.0604 (9)	0.0170 (9)	0.0138 (8)	−0.0034 (9)
C7	0.0906 (14)	0.0761 (13)	0.0697 (11)	0.0092 (11)	0.0269 (10)	−0.0153 (10)
C8	0.0871 (12)	0.0749 (11)	0.0527 (8)	−0.0212 (10)	0.0184 (8)	−0.0165 (8)
C9	0.0613 (9)	0.0745 (10)	0.0355 (6)	−0.0130 (8)	0.0029 (6)	0.0007 (6)
C10	0.0292 (5)	0.0326 (5)	0.0387 (5)	0.0014 (4)	0.0078 (4)	0.0082 (4)
C11	0.0309 (5)	0.0378 (5)	0.0321 (5)	−0.0065 (4)	0.0009 (4)	0.0051 (4)
C12	0.0933 (12)	0.0534 (8)	0.0457 (7)	−0.0229 (8)	0.0179 (8)	−0.0170 (6)
N1	0.0313 (4)	0.0328 (4)	0.0335 (4)	−0.0041 (4)	0.0076 (3)	0.0015 (4)
O1	0.0697 (7)	0.0685 (7)	0.0406 (5)	−0.0264 (6)	0.0089 (5)	−0.0073 (5)
O2	0.0657 (7)	0.0647 (6)	0.0372 (5)	−0.0238 (5)	0.0086 (4)	0.0042 (4)
O3	0.0563 (6)	0.0709 (7)	0.0348 (4)	0.0084 (5)	−0.0010 (4)	0.0028 (4)
O4	0.0364 (4)	0.0718 (7)	0.0358 (4)	0.0054 (4)	0.0060 (3)	0.0173 (5)
O5	0.0288 (4)	0.0571 (5)	0.0663 (6)	−0.0030 (4)	0.0082 (4)	0.0240 (5)

C1—O2	1.2019 (17)	C7—H7	0.93
C1—O1	1.2980 (18)	C8—C9	1.370 (3)
C1—C2	1.5281 (17)	C8—H8	0.93
C2—O3	1.4124 (19)	C9—H9	0.93
C2—C3	1.525 (3)	C10—O5	1.2398 (18)
C2—H2	0.98	C10—O4	1.2494 (16)
C3—H3A	0.96	C10—C11	1.5298 (15)
C3—H3B	0.96	C11—N1	1.4848 (17)
C3—H3C	0.96	C11—C12	1.524 (2)
C4—O3	1.3708 (19)	C11—H11	0.98
C4—C5	1.377 (2)	C12—H12A	0.96
C4—C9	1.393 (2)	C12—H12B	0.96
C5—C6	1.383 (3)	C12—H12C	0.96
C5—H5	0.93	N1—H1A	0.89
C6—C7	1.373 (3)	N1—H1B	0.89
C6—H6	0.93	N1—H1C	0.89
C7—C8	1.375 (3)	O1—H1O	1.03 (2)
O2—C1—O1	125.16 (12)	C9—C8—H8	120.1
O2—C1—C2	123.29 (12)	C7—C8—H8	120.1
O1—C1—C2	111.53 (12)	C8—C9—C4	120.31 (18)
O3—C2—C3	107.36 (15)	C8—C9—H9	119.8
O3—C2—C1	112.01 (12)	C4—C9—H9	119.8
C3—C2—C1	108.02 (12)	O5—C10—O4	126.77 (11)
O3—C2—H2	109.8	O5—C10—C11	117.18 (11)
C3—C2—H2	109.8	O4—C10—C11	115.99 (10)
C1—C2—H2	109.8	N1—C11—C12	108.94 (11)
C2—C3—H3A	109.5	N1—C11—C10	109.53 (9)
C2—C3—H3B	109.5	C12—C11—C10	110.39 (11)
H3A—C3—H3B	109.5	N1—C11—H11	109.3
C2—C3—H3C	109.5	C12—C11—H11	109.3
H3A—C3—H3C	109.5	C10—C11—H11	109.3
H3B—C3—H3C	109.5	C11—C12—H12A	109.5
O3—C4—C5	124.33 (13)	C11—C12—H12B	109.5
O3—C4—C9	115.83 (14)	H12A—C12—H12B	109.5
C5—C4—C9	119.82 (15)	C11—C12—H12C	109.5
C4—C5—C6	119.16 (15)	H12A—C12—H12C	109.5
C4—C5—H5	120.4	H12B—C12—H12C	109.5
C6—C5—H5	120.4	C11—N1—H1A	109.5
C7—C6—C5	120.85 (19)	C11—N1—H1B	109.5
C7—C6—H6	119.6	H1A—N1—H1B	109.5
C5—C6—H6	119.6	C11—N1—H1C	109.5
C6—C7—C8	120.01 (19)	H1A—N1—H1C	109.5
C6—C7—H7	120	H1B—N1—H1C	109.5
C8—C7—H7	120	C1—O1—H1O	114.0 (14)
C9—C8—C7	119.85 (17)	C4—O3—C2	117.36 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5i	0.89	2.05	2.916 (3)	165
N1—H1B···O5ii	0.89	1.94	2.822 (3)	170
N1—H1C···O2i	0.89	1.97	2.863 (3)	177
O1—H1O···O4ii	1.03 (2)	1.50 (2)	2.521 (3)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5i	0.89	2.05	2.916 (3)	165
N1—H1B⋯O5ii	0.89	1.94	2.822 (3)	170
N1—H1C⋯O2i	0.89	1.97	2.863 (3)	177
O1—H1O⋯O4ii	1.03 (2)	1.50 (2)	2.521 (3)	169 (2)

Symmetry codes: (i) ; (ii) .