Glycine–d-tartaric acid (1/1)

Mohandas, T.; Inbaseelan, C.R.D.; Saravanan, S.; Sakthivel, P.

doi:10.1107/S1600536813000822

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o236

doi:10.1107/S1600536813000822

Open

access

Glycine–D-tartaric acid (1/1)

T. Mohandas,^a C. Ranjith Dev Inbaseelan,^b S. Saravanan ^b and P. Sakthivel ^c ^*

^aDepartment of Physics, Shri Angalamman College of Engineering and Technology, Siruganoor, Tiruchirappalli 621 105, India, ^bCentre for Photonics and Nanotechnology, Sona College of Technology, Salem, Tamilnadu, India, and ^cDepartment of Physics, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, India
^*Correspondence e-mail: sakthi2udc@gmail.com

(Received 31 October 2012; accepted 9 January 2013; online 16 January 2013)

In the title co-crystal, C₂H₅NO₂·C₄H₆O₆, the gylcine molecule is present in the zwitterion form. In the tartaric acid molecule there is a short intramolecular O—H⋯O contact. In the crystal, the tartaric acid molecules are linked via pairs of O—H⋯O hydrogen bonds, forming inversion dimers. These dimers are linked via a number of O—H⋯O and N—H⋯O hydrogen bonds involving the two components, forming a three-dimensional network.

Related literature

For related structures, see: Kvick et al. (1980 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₂H₅NO₂·C₄H₆O₆
M_r = 225.16
Monoclinic, P 2₁ /n
a = 4.8387 (2) Å
b = 9.2913 (4) Å
c = 20.0273 (8) Å
β = 90.171 (1)°
V = 900.38 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.954, T_max = 0.969
12500 measured reflections
3282 independent reflections
2685 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.112
S = 1.07
3282 reflections
165 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.953 (19)	2.20 (2)	2.9509 (11)	135.2 (16)
N1—H1A⋯O3ⁱ	0.953 (19)	2.21 (2)	2.9386 (11)	132.2 (15)
N1—H1B⋯O6ⁱⁱ	0.909 (16)	2.041 (16)	2.9188 (10)	162.0 (14)
N1—H1C⋯O7ⁱⁱ	0.914 (18)	2.172 (17)	2.9492 (13)	142.4 (14)
O2—H2A⋯O8ⁱⁱⁱ	0.93 (2)	1.64 (2)	2.5473 (8)	167 (2)
O3—H3A⋯O4^iv	0.870 (18)	1.849 (18)	2.7122 (8)	171.0 (16)
O4—H4A⋯O3^v	0.81 (2)	2.09 (2)	2.7654 (10)	141.1 (18)
O4—H4A⋯O6	0.81 (2)	2.251 (18)	2.6743 (9)	112.9 (16)
O5—H5⋯O7	0.944 (19)	1.612 (19)	2.5459 (9)	169.2 (18)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z+1; (iv) x+1, y, z; (v) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT-NT (Bruker, 2004); data reduction: SAINT-NT and XPREP (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-32 (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813000822/bv2215sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813000822/bv2215Isup2.hkl

checkCIF report

Comment top

Glycine is the simplest aminoacid that is not optically active. It is essential for biosynthesis of nucleic acids as well as the biosynthesis of bile acids, creatine phosphate and other amino acids. Its geometric features of non covalent interactions at atomic resolution are important in the structural assembly and functions of proteins.

In the title compound(I), glycine is in the zwitterionic form. The tartaric acid molecule is in the un-ionized state. The angle between the planes of the half molecules O1/O2/C1/C2/O3 and O5/O6/C4/C3/O4 is 62.74 (3)°, which is closer to the value of 54.6° found in the structure of tartaric acid.

Atoms C5,C6,O7,N1 are planar with the N1 atom is slightly displaced out of this plane by -0.518 (1)°.

The relevant torsion angles are O7—C5—C6—N1 of -158.33 (3)° and O8—C5—C6—N1 of 23.08 (3)°. These can be compared with the corresponding values in pure Γ glycine 167.1 (1)° and -15.4 (1)°, respectively (Kvick et al., (1980), which is more distorted from planarity.

The molecular structure of (I) is shown in the (Fig.1) and selected geometric parameters listed in Table 1. The bond lengths for C=N, C=O, C—C are within normal ranges (Allen 2002). The dihedral angle between planes of D-tartaric acid and glycine is 51.14 (9)°. The molecules related by the 2₁ screw along b axis are linked by intermolecular O—H···O hydrogen bond generating a supramolecular chain.

The carbon skeleton of tartaric molecule is non-planar with a C1—C2—C3—C4 torsion angle of 177.8 (1)°. Fig.2 shows the packing diagram in which there are a large number of N—H···O and O—H···O hydrogen bonds.

Related literature top

For related structures, see: Kvick et al. (1980). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

Colourless single crystals were grown as transparent needles by slow evaporation method from a saturated aqueous solution containing glycine and D-tartaric acid in a 1:1 stoichiometric ratio.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT-NT (Bruker, 2004); data reduction: SAINT-NT and XPREP (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-32 (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure and labelling scheme for (I) with displacement ellipsoid of non-H atoms are drawn at the 30% probability level.
	Fig. 2. A packing diagram for (I) is shown. Dashed line indicates intra and inter molecular N—H..O and O—H..O hydrogen bonding interactions

Glycine–D-tartaric acid (1/1) top

Crystal data top

C₂H₅NO₂·C₄H₆O₆	F(000) = 472
M_r = 225.16	D_x = 1.661 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1585 reflections
a = 4.8387 (2) Å	θ = 2.0–25.0°
b = 9.2913 (4) Å	µ = 0.16 mm⁻¹
c = 20.0273 (8) Å	T = 293 K
β = 90.171 (1)°	Prism, colorless
V = 900.38 (6) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	2685 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 35.0°, θ_min = 2.0°
ω and ϕ scan	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2003)	k = −14→12
T_min = 0.954, T_max = 0.969	l = −27→29
12500 measured reflections	2 standard reflections every 100 reflections
3282 independent reflections	intensity decay: none

Refinement top

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0603P)² + 0.1264P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3282 reflections	Δρ_max = 0.49 e Å⁻³
165 parameters	Δρ_min = −0.22 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: 0.074 (5)

Crystal data top

C₂H₅NO₂·C₄H₆O₆	V = 900.38 (6) Å³
M_r = 225.16	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.8387 (2) Å	µ = 0.16 mm⁻¹
b = 9.2913 (4) Å	T = 293 K
c = 20.0273 (8) Å	0.30 × 0.20 × 0.20 mm
β = 90.171 (1)°

Data collection top

Bruker Kappa APEXII diffractometer	2685 reflections with I > 2σ(I)
Absorption correction: multi-scan (SADABS; Bruker, 2003)	R_int = 0.033
T_min = 0.954, T_max = 0.969	2 standard reflections every 100 reflections
12500 measured reflections	intensity decay: none
3282 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.49 e Å⁻³
3282 reflections	Δρ_min = −0.22 e Å⁻³
165 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

	x	y	z	U_iso*/U_eq
C1	0.44851 (16)	0.24734 (9)	0.61943 (4)	0.02360 (17)
C2	0.64567 (15)	0.25044 (9)	0.56018 (4)	0.02271 (17)
H2	0.7688	0.1668	0.5624	0.027*
C3	0.47689 (16)	0.24434 (9)	0.49514 (4)	0.02364 (17)
H3	0.3788	0.1521	0.4936	0.028*
C4	0.66706 (17)	0.25298 (9)	0.43493 (4)	0.02490 (18)
C5	1.19172 (16)	0.03299 (10)	0.29340 (4)	0.02399 (18)
C6	1.42473 (16)	0.05011 (10)	0.24364 (4)	0.02740 (19)
H6A	1.4296	0.1487	0.2278	0.033*
H6B	1.5996	0.0297	0.2655	0.033*
N1	1.38776 (19)	−0.04805 (10)	0.18645 (4)	0.03233 (19)
O1	0.44118 (15)	0.33804 (9)	0.66214 (4)	0.03694 (19)
O2	0.29078 (17)	0.13348 (8)	0.61631 (4)	0.0395 (2)
O3	0.80456 (13)	0.37788 (7)	0.56436 (3)	0.02782 (16)
O4	0.28015 (13)	0.35571 (8)	0.49377 (4)	0.03210 (17)
O5	0.83917 (16)	0.14540 (8)	0.43321 (4)	0.03596 (18)
O6	0.65303 (16)	0.35172 (9)	0.39549 (4)	0.03701 (19)
O7	1.15307 (17)	0.13761 (9)	0.33148 (4)	0.0417 (2)
O8	1.06398 (15)	−0.08344 (8)	0.29288 (4)	0.03465 (18)
H1A	1.257 (4)	−0.008 (2)	0.1562 (10)	0.074 (5)*
H1B	1.548 (3)	−0.0609 (17)	0.1637 (8)	0.054 (4)*
H1C	1.320 (3)	−0.1370 (19)	0.1966 (8)	0.054 (4)*
H2A	0.179 (4)	0.122 (2)	0.6533 (10)	0.084 (6)*
H3A	0.962 (4)	0.3630 (18)	0.5444 (8)	0.060 (5)*
H4A	0.323 (4)	0.419 (2)	0.4681 (9)	0.070 (5)*
H5	0.938 (4)	0.148 (2)	0.3926 (10)	0.072 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0228 (3)	0.0263 (4)	0.0218 (4)	−0.0020 (3)	0.0057 (3)	0.0023 (3)
C2	0.0223 (3)	0.0226 (4)	0.0233 (4)	−0.0009 (3)	0.0083 (3)	0.0002 (3)
C3	0.0237 (3)	0.0245 (4)	0.0228 (4)	−0.0023 (3)	0.0076 (3)	−0.0001 (3)
C4	0.0267 (3)	0.0266 (4)	0.0214 (4)	−0.0040 (3)	0.0066 (3)	−0.0039 (3)
C5	0.0221 (3)	0.0284 (4)	0.0215 (4)	0.0024 (3)	0.0093 (3)	0.0027 (3)
C6	0.0225 (3)	0.0333 (4)	0.0265 (4)	0.0000 (3)	0.0109 (3)	0.0026 (3)
N1	0.0387 (4)	0.0315 (4)	0.0269 (4)	0.0084 (3)	0.0162 (3)	0.0021 (3)
O1	0.0369 (3)	0.0426 (4)	0.0314 (4)	−0.0110 (3)	0.0154 (3)	−0.0113 (3)
O2	0.0484 (4)	0.0366 (4)	0.0335 (4)	−0.0202 (3)	0.0196 (3)	−0.0046 (3)
O3	0.0226 (3)	0.0297 (3)	0.0313 (3)	−0.0064 (2)	0.0107 (2)	−0.0030 (2)
O4	0.0259 (3)	0.0358 (4)	0.0347 (4)	0.0050 (2)	0.0120 (3)	0.0079 (3)
O5	0.0447 (4)	0.0324 (4)	0.0309 (4)	0.0075 (3)	0.0155 (3)	−0.0028 (3)
O6	0.0398 (4)	0.0399 (4)	0.0314 (4)	0.0031 (3)	0.0145 (3)	0.0089 (3)
O7	0.0490 (4)	0.0382 (4)	0.0380 (4)	−0.0039 (3)	0.0231 (3)	−0.0107 (3)
O8	0.0368 (3)	0.0314 (4)	0.0358 (4)	−0.0059 (3)	0.0189 (3)	0.0019 (3)

Geometric parameters (Å, º) top

C1—O1	1.2014 (11)	C5—O7	1.2499 (11)
C1—O2	1.3058 (10)	C5—C6	1.5153 (10)
C1—C2	1.5250 (10)	C6—N1	1.4746 (13)
C2—O3	1.4141 (10)	C6—H6A	0.9700
C2—C3	1.5364 (13)	C6—H6B	0.9700
C2—H2	0.9800	N1—H1A	0.953 (19)
C3—O4	1.4063 (11)	N1—H1B	0.909 (16)
C3—C4	1.5212 (10)	N1—H1C	0.914 (18)
C3—H3	0.9800	O2—H2A	0.93 (2)
C4—O6	1.2124 (11)	O3—H3A	0.870 (18)
C4—O5	1.3015 (11)	O4—H4A	0.81 (2)
C5—O8	1.2460 (11)	O5—H5	0.944 (19)

O1—C1—O2	125.71 (7)	O8—C5—C6	117.12 (7)
O1—C1—C2	124.10 (7)	O7—C5—C6	115.63 (8)
O2—C1—C2	110.19 (7)	N1—C6—C5	110.92 (7)
O3—C2—C1	108.12 (7)	N1—C6—H6A	109.5
O3—C2—C3	111.63 (7)	C5—C6—H6A	109.5
C1—C2—C3	109.07 (6)	N1—C6—H6B	109.5
O3—C2—H2	109.3	C5—C6—H6B	109.5
C1—C2—H2	109.3	H6A—C6—H6B	108.0
C3—C2—H2	109.3	C6—N1—H1A	109.2 (12)
O4—C3—C4	110.90 (7)	C6—N1—H1B	111.6 (10)
O4—C3—C2	110.33 (7)	H1A—N1—H1B	107.6 (15)
C4—C3—C2	110.42 (6)	C6—N1—H1C	115.4 (10)
O4—C3—H3	108.4	H1A—N1—H1C	105.0 (16)
C4—C3—H3	108.4	H1B—N1—H1C	107.6 (14)
C2—C3—H3	108.4	C1—O2—H2A	113.3 (13)
O6—C4—O5	126.76 (7)	C2—O3—H3A	108.3 (11)
O6—C4—C3	121.57 (8)	C3—O4—H4A	111.9 (14)
O5—C4—C3	111.66 (7)	C4—O5—H5	109.4 (11)
O8—C5—O7	127.24 (7)

O1—C1—C2—O3	−1.72 (12)	C1—C2—C3—C4	177.86 (7)
O2—C1—C2—O3	177.86 (8)	O4—C3—C4—O6	4.99 (12)
O1—C1—C2—C3	−123.29 (10)	C2—C3—C4—O6	−117.63 (9)
O2—C1—C2—C3	56.29 (9)	O4—C3—C4—O5	−175.95 (8)
O3—C2—C3—O4	−64.51 (8)	C2—C3—C4—O5	61.43 (9)
C1—C2—C3—O4	54.91 (8)	O8—C5—C6—N1	23.03 (11)
O3—C2—C3—C4	58.45 (8)	O7—C5—C6—N1	−158.29 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.953 (19)	2.20 (2)	2.9509 (11)	135.2 (16)
N1—H1A···O3ⁱ	0.953 (19)	2.21 (2)	2.9386 (11)	132.2 (15)
N1—H1B···O6ⁱⁱ	0.909 (16)	2.041 (16)	2.9188 (10)	162.0 (14)
N1—H1C···O7ⁱⁱ	0.914 (18)	2.172 (17)	2.9492 (13)	142.4 (14)
O2—H2A···O8ⁱⁱⁱ	0.93 (2)	1.64 (2)	2.5473 (8)	167 (2)
O3—H3A···O4^iv	0.870 (18)	1.849 (18)	2.7122 (8)	171.0 (16)
O4—H4A···O3^v	0.81 (2)	2.09 (2)	2.7654 (10)	141.1 (18)
O4—H4A···O6	0.81 (2)	2.251 (18)	2.6743 (9)	112.9 (16)
O5—H5···O7	0.944 (19)	1.612 (19)	2.5459 (9)	169.2 (18)

Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) −x+5/2, y−1/2, −z+1/2; (iii) −x+1, −y, −z+1; (iv) x+1, y, z; (v) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂H₅NO₂·C₄H₆O₆
M_r	225.16
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	4.8387 (2), 9.2913 (4), 20.0273 (8)
β (°)	90.171 (1)
V (Å³)	900.38 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.954, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	12500, 3282, 2685
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.806

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.112, 1.07
No. of reflections	3282
No. of parameters	165
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.22

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT-NT (Bruker, 2004), SAINT-NT and XPREP (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-32 (Farrugia, 2012), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.953 (19)	2.20 (2)	2.9509 (11)	135.2 (16)
N1—H1A···O3ⁱ	0.953 (19)	2.21 (2)	2.9386 (11)	132.2 (15)
N1—H1B···O6ⁱⁱ	0.909 (16)	2.041 (16)	2.9188 (10)	162.0 (14)
N1—H1C···O7ⁱⁱ	0.914 (18)	2.172 (17)	2.9492 (13)	142.4 (14)
O2—H2A···O8ⁱⁱⁱ	0.93 (2)	1.64 (2)	2.5473 (8)	167 (2)
O3—H3A···O4^iv	0.870 (18)	1.849 (18)	2.7122 (8)	171.0 (16)
O4—H4A···O3^v	0.81 (2)	2.09 (2)	2.7654 (10)	141.1 (18)
O4—H4A···O6	0.81 (2)	2.251 (18)	2.6743 (9)	112.9 (16)
O5—H5···O7	0.944 (19)	1.612 (19)	2.5459 (9)	169.2 (18)

Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) −x+5/2, y−1/2, −z+1/2; (iii) −x+1, −y, −z+1; (iv) x+1, y, z; (v) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank Sona Engineering College, Salem, for providing the sample to carry out the X-ray study.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2003). SADABS, SAINT-NT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kvick, Å., Canning, W. M., Koetzle, T. F. & Williams, G. J. B. (1980). Acta Cryst. B36, 115–120. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar