# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_gta293K
_database_code_depnum_ccdc_archive 'CCDC 1435507'
_audit_update_record             
;
2016-06-02 deposited with the CCDC.
2016-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'glycine-DL-tartaric acid (1:1)'
_chemical_name_common            'glycine-DL-tartaric acid (1:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 O6, C2 H5 N O2'
_chemical_formula_sum            'C6 H11 N O8'
_chemical_formula_weight         225.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.8563(7)
_cell_length_b                   9.3274(9)
_cell_length_c                   20.671(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.494(11)
_cell_angle_gamma                90
_cell_volume                     910.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5284
_cell_measurement_theta_min      2.04
_cell_measurement_theta_max      29.40

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.156
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.500
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            8609
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.026
_diffrn_reflns_theta_max         29.275
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2463
_reflns_number_gt                1383
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'STOE X-AREA (Stoe & Cie, 2006)'
_computing_cell_refinement       'STOE X-AREA (Stoe & Cie, 2006)'
_computing_data_reduction        'STOE X-RED (Stoe & Cie, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  
;
Mercury (Macrae et al., 2006), 
PLATON (Spek, 2009),
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2463
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   0.870
_refine_ls_restrained_S_all      0.870
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.7597(2) 0.12250(11) 0.56430(5) 0.0350(3) Uani 1 1 d . . . . .
H6 H 0.573(4) 0.1346(18) 0.5415(9) 0.042 Uiso 1 1 d . U . . .
O3 O 0.5948(3) 0.35411(12) 0.43315(6) 0.0436(3) Uani 1 1 d . . . . .
H3 H 0.459(4) 0.360(2) 0.3961(10) 0.052 Uiso 1 1 d . U . . .
O5 O 1.2133(2) 0.14428(13) 0.49382(6) 0.0398(3) Uani 1 1 d . . . . .
H5 H 1.143(4) 0.078(2) 0.4702(9) 0.048 Uiso 1 1 d . U . . .
O8 O 1.2211(2) 0.16221(13) 0.66219(6) 0.0446(3) Uani 1 1 d . . . . .
O7 O 1.3240(3) 0.36655(13) 0.61616(6) 0.0477(3) Uani 1 1 d . . . . .
H7 H 1.4623 0.3667 0.6477 0.057 Uiso 1 1 calc R U . . .
O4 O 0.7420(2) 0.14892(13) 0.39542(6) 0.0451(3) Uani 1 1 d . . . . .
O1 O 1.2295(2) 0.58298(12) 0.29287(6) 0.0422(3) Uani 1 1 d . . . . .
C3 C 0.7680(3) 0.24723(15) 0.43505(7) 0.0321(3) Uani 1 1 d . . . . .
O2 O 1.1789(3) 0.36274(13) 0.33149(6) 0.0495(3) Uani 1 1 d . . . . .
C5 C 0.9158(3) 0.24919(16) 0.56019(7) 0.0302(3) Uani 1 1 d . . . . .
H5A H 0.807(4) 0.3309(18) 0.5627(8) 0.036 Uiso 1 1 d . U . . .
C2 C 1.1015(3) 0.46692(15) 0.29321(7) 0.0312(3) Uani 1 1 d . . . . .
C6 C 1.1702(3) 0.25281(16) 0.61927(7) 0.0310(3) Uani 1 1 d . . . . .
C4 C 1.0170(3) 0.25543(16) 0.49500(7) 0.0317(3) Uani 1 1 d . . . . .
H4 H 1.107(4) 0.3448(19) 0.4929(8) 0.038 Uiso 1 1 d . U . . .
N1 N 0.7983(3) 0.54803(16) 0.18658(7) 0.0400(3) Uani 1 1 d . . . . .
H1A H 0.614(5) 0.568(2) 0.1645(10) 0.060 Uiso 1 1 d . U . . .
H1B H 0.861(5) 0.632(2) 0.2008(10) 0.060 Uiso 1 1 d . U . . .
H1C H 0.898(4) 0.507(2) 0.1597(10) 0.060 Uiso 1 1 d . U . . .
C1 C 0.8200(3) 0.45011(18) 0.24357(8) 0.0355(4) Uani 1 1 d . . . . .
H1D H 0.677(4) 0.4741(18) 0.2635(8) 0.043 Uiso 1 1 d . U . . .
H1E H 0.794(4) 0.352(2) 0.2278(9) 0.043 Uiso 1 1 d . U . . .


_geom_special_details            
;
 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.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O6 C5 1.4171(18) . ?
O6 H6 0.92(2) . ?
O3 C3 1.2991(18) . ?
O3 H3 0.89(2) . ?
O5 C4 1.4127(19) . ?
O5 H5 0.81(2) . ?
O8 C6 1.2083(18) . ?
O7 C6 1.3078(18) . ?
O7 H7 0.8200 . ?
O4 C3 1.2164(18) . ?
O1 C2 1.2492(18) . ?
C3 C4 1.518(2) . ?
O2 C2 1.2541(18) . ?
C5 C6 1.521(2) . ?
C5 C4 1.539(2) . ?
C5 H5A 0.934(17) . ?
C2 C1 1.514(2) . ?
C4 H4 0.947(18) . ?
N1 C1 1.475(2) . ?
N1 H1A 0.92(2) . ?
N1 H1B 0.87(2) . ?
N1 H1C 0.90(2) . ?
C1 H1D 0.914(18) . ?
C1 H1E 0.968(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O6 H6 110.0(11) . . ?
C3 O3 H3 114.6(12) . . ?
C4 O5 H5 112.5(14) . . ?
C6 O7 H7 109.5 . . ?
O4 C3 O3 126.40(14) . . ?
O4 C3 C4 121.71(13) . . ?
O3 C3 C4 111.89(13) . . ?
O6 C5 C6 108.41(12) . . ?
O6 C5 C4 111.62(12) . . ?
C6 C5 C4 109.67(12) . . ?
O6 C5 H5A 111.1(10) . . ?
C6 C5 H5A 107.5(11) . . ?
C4 C5 H5A 108.4(10) . . ?
O1 C2 O2 126.78(14) . . ?
O1 C2 C1 117.25(13) . . ?
O2 C2 C1 115.96(13) . . ?
O8 C6 O7 125.58(14) . . ?
O8 C6 C5 124.25(13) . . ?
O7 C6 C5 110.17(12) . . ?
O5 C4 C3 111.18(12) . . ?
O5 C4 C5 109.99(12) . . ?
C3 C4 C5 110.89(12) . . ?
O5 C4 H4 108.9(10) . . ?
C3 C4 H4 107.2(10) . . ?
C5 C4 H4 108.6(10) . . ?
C1 N1 H1A 113.6(12) . . ?
C1 N1 H1B 109.7(14) . . ?
H1A N1 H1B 102.0(19) . . ?
C1 N1 H1C 106.2(13) . . ?
H1A N1 H1C 112.2(18) . . ?
H1B N1 H1C 113(2) . . ?
N1 C1 C2 111.25(13) . . ?
N1 C1 H1D 106.7(11) . . ?
C2 C1 H1D 109.3(11) . . ?
N1 C1 H1E 109.6(11) . . ?
C2 C1 H1E 110.6(11) . . ?
H1D C1 H1E 109.2(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 C5 C6 O8 -1.2(2) . . . . ?
C4 C5 C6 O8 -123.29(16) . . . . ?
O6 C5 C6 O7 178.24(12) . . . . ?
C4 C5 C6 O7 56.14(17) . . . . ?
O4 C3 C4 O5 5.0(2) . . . . ?
O3 C3 C4 O5 -175.83(12) . . . . ?
O4 C3 C4 C5 -117.70(16) . . . . ?
O3 C3 C4 C5 61.46(16) . . . . ?
O6 C5 C4 O5 -65.36(16) . . . . ?
C6 C5 C4 O5 54.81(16) . . . . ?
O6 C5 C4 C3 58.04(16) . . . . ?
C6 C5 C4 C3 178.20(12) . . . . ?
O1 C2 C1 N1 22.8(2) . . . . ?
O2 C2 C1 N1 -158.61(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H6 O5 0.92(2) 1.80(2) 2.7203(16) 175.2(16) 1_455
O3 H3 O2 0.89(2) 1.67(2) 2.5538(17) 173.3(19) 1_455
O5 H5 O6 0.81(2) 2.091(19) 2.7795(16) 142.3(18) 3_756
O7 H7 O1 0.82 1.76 2.5606(16) 163.5 3_866
N1 H1C O6 0.90(2) 2.28(2) 2.9553(18) 131.8(17) 4_565
N1 H1C O8 0.90(2) 2.22(2) 2.9665(19) 140.0(17) 4_565
N1 H1A O4 0.92(2) 2.02(2) 2.9273(19) 165.7(18) 2_655
N1 H1B O2 0.87(2) 2.25(2) 2.9645(19) 140.0(18) 2_755

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.045

