# 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_gta275K
_database_code_depnum_ccdc_archive 'CCDC 1437082'
_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                   4.8492(8)
_cell_length_b                   9.3222(11)
_cell_length_c                   20.646(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.324(13)
_cell_angle_gamma                90
_cell_volume                     908.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    275(2)
_cell_measurement_reflns_used    3792
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      29.41

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.647
_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    0.157
_shelx_estimated_absorpt_T_min   0.941
_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      275(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            8020
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_av_R_equivalents  0.0525
_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         2.027
_diffrn_reflns_theta_max         29.164
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2454
_reflns_number_gt                1209
_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)+(0.0542P)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       0.023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2454
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   0.843
_refine_ls_restrained_S_all      0.843
_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 0.7600(3) 0.12202(14) 0.56451(7) 0.0330(3) Uani 1 1 d . . . . .
H6 H 0.579(5) 0.136(2) 0.5422(11) 0.040 Uiso 1 1 d . U . . .
O3 O 0.5954(3) 0.35444(15) 0.43298(7) 0.0402(4) Uani 1 1 d . . . . .
H3 H 0.451(5) 0.359(2) 0.3935(11) 0.048 Uiso 1 1 d . U . . .
O5 O 1.2146(3) 0.14456(16) 0.49370(7) 0.0371(3) Uani 1 1 d . . . . .
H5 H 1.148(5) 0.076(2) 0.4704(11) 0.045 Uiso 1 1 d . U . . .
O8 O 1.2210(3) 0.16119(15) 0.66237(7) 0.0410(4) Uani 1 1 d . . . . .
O7 O 1.3246(3) 0.36638(15) 0.61636(7) 0.0441(4) Uani 1 1 d . . . . .
H7 H 1.4604 0.3675 0.6485 0.053 Uiso 1 1 calc R U . . .
O4 O 0.7431(3) 0.14848(16) 0.39545(7) 0.0415(4) Uani 1 1 d . . . . .
O1 O 1.2285(3) 0.58380(14) 0.29304(7) 0.0384(4) Uani 1 1 d . . . . .
C3 C 0.7693(4) 0.2472(2) 0.43501(9) 0.0300(4) Uani 1 1 d . . . . .
O2 O 1.1790(3) 0.36254(16) 0.33158(7) 0.0454(4) Uani 1 1 d . . . . .
C5 C 0.9158(4) 0.2490(2) 0.56041(9) 0.0278(4) Uani 1 1 d . . . . .
H5A H 0.804(4) 0.332(2) 0.5610(9) 0.033 Uiso 1 1 d . U . . .
C2 C 1.1003(4) 0.4670(2) 0.29318(9) 0.0297(4) Uani 1 1 d . . . . .
C6 C 1.1708(4) 0.2523(2) 0.61930(9) 0.0290(4) Uani 1 1 d . . . . .
C4 C 1.0176(4) 0.2556(2) 0.49520(9) 0.0298(4) Uani 1 1 d . . . . .
H4 H 1.107(4) 0.346(2) 0.4930(10) 0.036 Uiso 1 1 d . U . . .
N1 N 0.7974(4) 0.5483(2) 0.18669(8) 0.0370(4) Uani 1 1 d . . . . .
H1A H 0.607(5) 0.565(3) 0.1643(11) 0.055 Uiso 1 1 d . U . . .
H1B H 0.858(5) 0.637(3) 0.2022(12) 0.055 Uiso 1 1 d . U . . .
H1C H 0.900(5) 0.510(3) 0.1600(11) 0.055 Uiso 1 1 d . U . . .
C1 C 0.8195(4) 0.4501(2) 0.24383(10) 0.0332(4) Uani 1 1 d . . . . .
H1D H 0.670(5) 0.473(2) 0.2638(10) 0.040 Uiso 1 1 d . U . . .
H1E H 0.792(4) 0.351(2) 0.2275(11) 0.040 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 1.417(2) . ?
O6 H6 0.90(2) . ?
O3 C3 1.303(2) . ?
O3 H3 0.95(2) . ?
O5 C4 1.413(2) . ?
O5 H5 0.82(2) . ?
O8 C6 1.213(2) . ?
O7 C6 1.308(2) . ?
O7 H7 0.8200 . ?
O4 C3 1.217(2) . ?
O1 C2 1.254(2) . ?
C3 C4 1.520(3) . ?
O2 C2 1.258(2) . ?
C5 C6 1.522(3) . ?
C5 C4 1.538(3) . ?
C5 H5A 0.95(2) . ?
C2 C1 1.509(3) . ?
C4 H4 0.96(2) . ?
N1 C1 1.477(3) . ?
N1 H1A 0.95(3) . ?
N1 H1B 0.91(3) . ?
N1 H1C 0.90(2) . ?
C1 H1D 0.94(2) . ?
C1 H1E 0.98(2) . ?

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 108.6(14) . . ?
C3 O3 H3 114.2(14) . . ?
C4 O5 H5 113.9(17) . . ?
C6 O7 H7 109.5 . . ?
O4 C3 O3 126.29(17) . . ?
O4 C3 C4 121.88(17) . . ?
O3 C3 C4 111.82(16) . . ?
O6 C5 C6 108.38(15) . . ?
O6 C5 C4 111.62(15) . . ?
C6 C5 C4 109.45(15) . . ?
O6 C5 H5A 111.8(12) . . ?
C6 C5 H5A 109.5(13) . . ?
C4 C5 H5A 106.1(12) . . ?
O1 C2 O2 126.51(18) . . ?
O1 C2 C1 117.35(17) . . ?
O2 C2 C1 116.12(17) . . ?
O8 C6 O7 125.65(17) . . ?
O8 C6 C5 124.07(17) . . ?
O7 C6 C5 110.28(15) . . ?
O5 C4 C3 110.88(15) . . ?
O5 C4 C5 110.16(16) . . ?
C3 C4 C5 111.08(15) . . ?
O5 C4 H4 109.2(12) . . ?
C3 C4 H4 106.9(13) . . ?
C5 C4 H4 108.5(12) . . ?
C1 N1 H1A 112.2(14) . . ?
C1 N1 H1B 108.8(15) . . ?
H1A N1 H1B 103(2) . . ?
C1 N1 H1C 107.0(15) . . ?
H1A N1 H1C 113(2) . . ?
H1B N1 H1C 114(2) . . ?
N1 C1 C2 111.26(16) . . ?
N1 C1 H1D 106.7(13) . . ?
C2 C1 H1D 110.3(13) . . ?
N1 C1 H1E 109.3(12) . . ?
C2 C1 H1E 111.1(13) . . ?
H1D C1 H1E 108.0(18) . . ?

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 -1.6(2) . . . . ?
C4 C5 C6 O8 -123.58(19) . . . . ?
O6 C5 C6 O7 178.32(15) . . . . ?
C4 C5 C6 O7 56.4(2) . . . . ?
O4 C3 C4 O5 5.6(2) . . . . ?
O3 C3 C4 O5 -175.48(15) . . . . ?
O4 C3 C4 C5 -117.21(19) . . . . ?
O3 C3 C4 C5 61.7(2) . . . . ?
O6 C5 C4 O5 -65.26(19) . . . . ?
C6 C5 C4 O5 54.7(2) . . . . ?
O6 C5 C4 C3 58.0(2) . . . . ?
C6 C5 C4 C3 177.99(15) . . . . ?
O1 C2 C1 N1 23.0(2) . . . . ?
O2 C2 C1 N1 -158.52(17) . . . . ?

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 0.90(2) 1.82(2) 2.7194(19) 174(2) 1_455
O3 H3 O2 0.95(2) 1.61(2) 2.553(2) 173(2) 1_455
O5 H5 O6 0.82(2) 2.07(2) 2.7755(19) 144(2) 3_756
O7 H7 O1 0.82 1.76 2.558(2) 163.6 3_866
N1 H1C O6 0.90(2) 2.29(2) 2.951(2) 130(2) 4_565
N1 H1C O8 0.90(2) 2.22(2) 2.960(2) 139.4(19) 4_565
N1 H1A O4 0.95(3) 2.01(3) 2.927(2) 163(2) 2_655
N1 H1B O2 0.91(3) 2.21(3) 2.959(2) 139(2) 2_755

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_gta250K
_database_code_depnum_ccdc_archive 'CCDC 1437083'
_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                   4.8433(7)
_cell_length_b                   9.3162(10)
_cell_length_c                   20.618(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.172(12)
_cell_angle_gamma                90
_cell_volume                     905.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    3930
_cell_measurement_theta_min      1.98
_cell_measurement_theta_max      29.41

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.651
_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    0.157
_shelx_estimated_absorpt_T_min   0.941
_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      250(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            7992
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_av_R_equivalents  0.0547
_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         2.029
_diffrn_reflns_theta_max         29.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2443
_reflns_number_gt                1254
_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)+(0.0589P)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       0.024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2443
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_restrained_S_all      0.900
_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 0.7600(3) 0.12176(14) 0.56454(7) 0.0310(3) Uani 1 1 d . . . . .
H6 H 0.575(5) 0.133(2) 0.5420(11) 0.037 Uiso 1 1 d . U . . .
O3 O 0.5961(3) 0.35445(16) 0.43308(8) 0.0379(4) Uani 1 1 d . . . . .
H3 H 0.453(5) 0.360(3) 0.3943(12) 0.045 Uiso 1 1 d . U . . .
O5 O 1.2162(3) 0.14466(17) 0.49352(8) 0.0345(4) Uani 1 1 d . . . . .
H5 H 1.141(5) 0.076(3) 0.4687(12) 0.041 Uiso 1 1 d . U . . .
O8 O 1.2211(3) 0.16082(16) 0.66239(7) 0.0378(4) Uani 1 1 d . . . . .
O7 O 1.3249(3) 0.36615(16) 0.61633(8) 0.0408(4) Uani 1 1 d . . . . .
H7 H 1.4637 0.3666 0.6485 0.049 Uiso 1 1 calc R U . . .
O4 O 0.7439(3) 0.14816(17) 0.39548(7) 0.0387(4) Uani 1 1 d . . . . .
O1 O 1.2273(3) 0.58435(15) 0.29304(7) 0.0357(4) Uani 1 1 d . . . . .
C3 C 0.7701(4) 0.2472(2) 0.43522(9) 0.0279(4) Uani 1 1 d . . . . .
O2 O 1.1792(3) 0.36236(17) 0.33160(8) 0.0420(4) Uani 1 1 d . . . . .
C5 C 0.9159(4) 0.2491(2) 0.56056(9) 0.0260(4) Uani 1 1 d . . . . .
H5A H 0.805(5) 0.333(2) 0.5622(10) 0.031 Uiso 1 1 d . U . . .
C2 C 1.1000(4) 0.4671(2) 0.29327(9) 0.0274(4) Uani 1 1 d . . . . .
C6 C 1.1704(4) 0.2520(2) 0.61932(9) 0.0272(4) Uani 1 1 d . . . . .
C4 C 1.0180(4) 0.2558(2) 0.49520(10) 0.0281(4) Uani 1 1 d . . . . .
H4 H 1.108(5) 0.347(3) 0.4939(11) 0.034 Uiso 1 1 d . U . . .
N1 N 0.7969(4) 0.5483(2) 0.18676(9) 0.0342(4) Uani 1 1 d . . . . .
H1A H 0.611(6) 0.566(3) 0.1639(12) 0.051 Uiso 1 1 d . U . . .
H1B H 0.859(6) 0.635(3) 0.2019(13) 0.051 Uiso 1 1 d . U . . .
H1C H 0.900(5) 0.510(3) 0.1587(12) 0.051 Uiso 1 1 d . U . . .
C1 C 0.8189(4) 0.4502(2) 0.24388(10) 0.0312(5) Uani 1 1 d . . . . .
H1D H 0.671(5) 0.472(2) 0.2640(11) 0.037 Uiso 1 1 d . U . . .
H1E H 0.790(5) 0.350(3) 0.2276(11) 0.037 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 1.419(2) . ?
O6 H6 0.92(3) . ?
O3 C3 1.301(2) . ?
O3 H3 0.93(3) . ?
O5 C4 1.417(2) . ?
O5 H5 0.85(3) . ?
O8 C6 1.213(2) . ?
O7 C6 1.310(2) . ?
O7 H7 0.8300 . ?
O4 C3 1.221(2) . ?
O1 C2 1.255(2) . ?
C3 C4 1.517(3) . ?
O2 C2 1.259(2) . ?
C5 C6 1.519(3) . ?
C5 C4 1.539(3) . ?
C5 H5A 0.96(2) . ?
C2 C1 1.511(3) . ?
C4 H4 0.96(2) . ?
N1 C1 1.475(3) . ?
N1 H1A 0.93(3) . ?
N1 H1B 0.89(3) . ?
N1 H1C 0.92(3) . ?
C1 H1D 0.93(2) . ?
C1 H1E 0.99(2) . ?

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 110.3(14) . . ?
C3 O3 H3 115.0(15) . . ?
C4 O5 H5 111.4(17) . . ?
C6 O7 H7 109.5 . . ?
O4 C3 O3 126.13(19) . . ?
O4 C3 C4 121.92(17) . . ?
O3 C3 C4 111.93(16) . . ?
O6 C5 C6 108.34(15) . . ?
O6 C5 C4 111.46(15) . . ?
C6 C5 C4 109.48(16) . . ?
O6 C5 H5A 111.9(13) . . ?
C6 C5 H5A 108.6(13) . . ?
C4 C5 H5A 107.1(12) . . ?
O1 C2 O2 126.68(19) . . ?
O1 C2 C1 117.13(17) . . ?
O2 C2 C1 116.17(17) . . ?
O8 C6 O7 125.49(18) . . ?
O8 C6 C5 124.31(18) . . ?
O7 C6 C5 110.20(16) . . ?
O5 C4 C3 110.87(16) . . ?
O5 C4 C5 110.28(16) . . ?
C3 C4 C5 111.05(16) . . ?
O5 C4 H4 109.6(13) . . ?
C3 C4 H4 107.6(14) . . ?
C5 C4 H4 107.4(13) . . ?
C1 N1 H1A 113.6(15) . . ?
C1 N1 H1B 108.9(17) . . ?
H1A N1 H1B 103(2) . . ?
C1 N1 H1C 108.0(15) . . ?
H1A N1 H1C 111(2) . . ?
H1B N1 H1C 113(2) . . ?
N1 C1 C2 111.32(17) . . ?
N1 C1 H1D 107.2(14) . . ?
C2 C1 H1D 110.1(14) . . ?
N1 C1 H1E 109.6(13) . . ?
C2 C1 H1E 111.3(14) . . ?
H1D C1 H1E 107.1(19) . . ?

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 -1.7(3) . . . . ?
C4 C5 C6 O8 -123.5(2) . . . . ?
O6 C5 C6 O7 178.11(16) . . . . ?
C4 C5 C6 O7 56.4(2) . . . . ?
O4 C3 C4 O5 5.8(3) . . . . ?
O3 C3 C4 O5 -175.17(16) . . . . ?
O4 C3 C4 C5 -117.2(2) . . . . ?
O3 C3 C4 C5 61.9(2) . . . . ?
O6 C5 C4 O5 -65.4(2) . . . . ?
C6 C5 C4 O5 54.5(2) . . . . ?
O6 C5 C4 C3 57.9(2) . . . . ?
C6 C5 C4 C3 177.77(16) . . . . ?
O1 C2 C1 N1 23.2(3) . . . . ?
O2 C2 C1 N1 -158.35(18) . . . . ?

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(3) 1.80(3) 2.715(2) 176(2) 1_455
O3 H3 O2 0.93(3) 1.63(3) 2.556(2) 174(2) 1_455
O5 H5 O6 0.85(3) 2.06(2) 2.769(2) 141(2) 3_756
O7 H7 O1 0.83 1.75 2.561(2) 163.5 3_866
N1 H1C O6 0.92(3) 2.26(3) 2.947(2) 131(2) 4_565
N1 H1C O8 0.92(3) 2.21(3) 2.956(2) 138(2) 4_565
N1 H1A O4 0.93(3) 2.02(3) 2.929(2) 165(2) 2_655
N1 H1B O2 0.89(3) 2.22(3) 2.956(2) 139(2) 2_755

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_gta225
_database_code_depnum_ccdc_archive 'CCDC 1437084'
_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                   4.8349(7)
_cell_length_b                   9.3138(10)
_cell_length_c                   20.579(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.032(12)
_cell_angle_gamma                90
_cell_volume                     902.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    225(2)
_cell_measurement_reflns_used    4219
_cell_measurement_theta_min      2.03
_cell_measurement_theta_max      29.41

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.656
_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    0.157
_shelx_estimated_absorpt_T_min   0.941
_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      225(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            7988
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_av_R_equivalents  0.0472
_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         2.032
_diffrn_reflns_theta_max         29.181
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2439
_reflns_number_gt                1340
_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)+(0.0499P)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       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2439
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0786
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_restrained_S_all      0.874
_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 0.7604(3) 0.12128(12) 0.56465(6) 0.0272(3) Uani 1 1 d . . . . .
H6 H 0.576(5) 0.132(2) 0.5421(10) 0.033 Uiso 1 1 d . U . . .
O3 O 0.5967(3) 0.35471(13) 0.43295(6) 0.0331(3) Uani 1 1 d . . . . .
H3 H 0.452(5) 0.361(2) 0.3949(10) 0.040 Uiso 1 1 d . U . . .
O5 O 1.2175(3) 0.14495(14) 0.49354(6) 0.0308(3) Uani 1 1 d . . . . .
H5 H 1.148(5) 0.077(2) 0.4717(10) 0.037 Uiso 1 1 d . U . . .
O8 O 1.2210(3) 0.16003(14) 0.66253(6) 0.0331(3) Uani 1 1 d . . . . .
O7 O 1.3258(3) 0.36593(14) 0.61649(6) 0.0359(3) Uani 1 1 d . . . . .
H7 H 1.4654 0.3658 0.6485 0.043 Uiso 1 1 calc R U . . .
O4 O 0.7445(3) 0.14772(14) 0.39556(6) 0.0339(3) Uani 1 1 d . . . . .
O1 O 1.2261(3) 0.58485(13) 0.29321(6) 0.0318(3) Uani 1 1 d . . . . .
C3 C 0.7706(4) 0.24726(18) 0.43518(8) 0.0252(4) Uani 1 1 d . . . . .
O2 O 1.1792(3) 0.36249(14) 0.33156(6) 0.0372(3) Uani 1 1 d . . . . .
C5 C 0.9164(4) 0.24892(18) 0.56069(8) 0.0231(3) Uani 1 1 d . . . . .
H5A H 0.804(4) 0.333(2) 0.5627(9) 0.028 Uiso 1 1 d . U . . .
C2 C 1.0999(4) 0.46705(17) 0.29339(8) 0.0244(4) Uani 1 1 d . . . . .
C6 C 1.1706(4) 0.25178(17) 0.61950(8) 0.0242(4) Uani 1 1 d . . . . .
C4 C 1.0187(4) 0.25606(19) 0.49497(8) 0.0250(4) Uani 1 1 d . . . . .
H4 H 1.110(4) 0.346(2) 0.4933(9) 0.030 Uiso 1 1 d . U . . .
N1 N 0.7958(4) 0.54878(17) 0.18671(8) 0.0301(4) Uani 1 1 d . . . . .
H1A H 0.607(5) 0.567(2) 0.1635(10) 0.045 Uiso 1 1 d . U . . .
H1B H 0.858(5) 0.634(3) 0.2014(11) 0.045 Uiso 1 1 d . U . . .
H1C H 0.899(5) 0.507(2) 0.1602(10) 0.045 Uiso 1 1 d . U . . .
C1 C 0.8182(4) 0.44987(19) 0.24415(9) 0.0271(4) Uani 1 1 d . . . . .
H1D H 0.666(4) 0.474(2) 0.2651(9) 0.032 Uiso 1 1 d . U . . .
H1E H 0.790(4) 0.351(2) 0.2274(10) 0.032 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 1.420(2) . ?
O6 H6 0.91(2) . ?
O3 C3 1.301(2) . ?
O3 H3 0.93(2) . ?
O5 C4 1.417(2) . ?
O5 H5 0.80(2) . ?
O8 C6 1.215(2) . ?
O7 C6 1.311(2) . ?
O7 H7 0.8300 . ?
O4 C3 1.222(2) . ?
O1 C2 1.256(2) . ?
C3 C4 1.515(2) . ?
O2 C2 1.256(2) . ?
C5 C6 1.518(2) . ?
C5 C4 1.543(2) . ?
C5 H5A 0.958(19) . ?
C2 C1 1.512(2) . ?
C4 H4 0.95(2) . ?
N1 C1 1.483(2) . ?
N1 H1A 0.95(2) . ?
N1 H1B 0.88(2) . ?
N1 H1C 0.91(2) . ?
C1 H1D 0.958(19) . ?
C1 H1E 0.98(2) . ?

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 110.4(12) . . ?
C3 O3 H3 115.7(13) . . ?
C4 O5 H5 112.5(16) . . ?
C6 O7 H7 109.5 . . ?
O4 C3 O3 126.24(16) . . ?
O4 C3 C4 121.77(15) . . ?
O3 C3 C4 111.98(14) . . ?
O6 C5 C6 108.30(13) . . ?
O6 C5 C4 111.46(13) . . ?
C6 C5 C4 109.65(13) . . ?
O6 C5 H5A 111.6(11) . . ?
C6 C5 H5A 108.4(12) . . ?
C4 C5 H5A 107.4(11) . . ?
O2 C2 O1 126.83(16) . . ?
O2 C2 C1 116.04(15) . . ?
O1 C2 C1 117.09(15) . . ?
O8 C6 O7 125.60(16) . . ?
O8 C6 C5 124.18(15) . . ?
O7 C6 C5 110.22(14) . . ?
O5 C4 C3 111.12(14) . . ?
O5 C4 C5 109.86(14) . . ?
C3 C4 C5 110.98(14) . . ?
O5 C4 H4 108.7(12) . . ?
C3 C4 H4 107.9(12) . . ?
C5 C4 H4 108.3(11) . . ?
C1 N1 H1A 113.8(13) . . ?
C1 N1 H1B 109.4(14) . . ?
H1A N1 H1B 103(2) . . ?
C1 N1 H1C 105.2(13) . . ?
H1A N1 H1C 111.9(18) . . ?
H1B N1 H1C 114(2) . . ?
N1 C1 C2 111.18(14) . . ?
N1 C1 H1D 106.8(11) . . ?
C2 C1 H1D 110.0(11) . . ?
N1 C1 H1E 108.9(11) . . ?
C2 C1 H1E 111.5(12) . . ?
H1D C1 H1E 108.4(16) . . ?

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 -1.6(2) . . . . ?
C4 C5 C6 O8 -123.43(17) . . . . ?
O6 C5 C6 O7 177.93(13) . . . . ?
C4 C5 C6 O7 56.11(18) . . . . ?
O4 C3 C4 O5 5.7(2) . . . . ?
O3 C3 C4 O5 -175.12(13) . . . . ?
O4 C3 C4 C5 -116.85(17) . . . . ?
O3 C3 C4 C5 62.32(18) . . . . ?
O6 C5 C4 O5 -65.51(17) . . . . ?
C6 C5 C4 O5 54.40(18) . . . . ?
O6 C5 C4 C3 57.77(18) . . . . ?
C6 C5 C4 C3 177.68(13) . . . . ?
O2 C2 C1 N1 -158.38(15) . . . . ?
O1 C2 C1 N1 23.5(2) . . . . ?

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 0.91(2) 1.80(2) 2.7106(18) 176.1(18) 1_455
O3 H3 O2 0.93(2) 1.63(2) 2.5561(19) 175(2) 1_455
O5 H5 O6 0.80(2) 2.08(2) 2.7661(17) 143(2) 3_756
O7 H7 O1 0.83 1.75 2.5576(18) 163.3 3_866
N1 H1C O6 0.91(2) 2.27(2) 2.942(2) 130.8(18) 4_565
N1 H1C O8 0.91(2) 2.19(2) 2.952(2) 140.8(17) 4_565
N1 H1A O4 0.95(2) 2.00(2) 2.923(2) 165.2(19) 2_655
N1 H1B O2 0.88(2) 2.22(2) 2.952(2) 139.6(19) 2_755

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_gta200K
_database_code_depnum_ccdc_archive 'CCDC 1437085'
_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                   4.8273(7)
_cell_length_b                   9.3086(9)
_cell_length_c                   20.535(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.850(11)
_cell_angle_gamma                90
_cell_volume                     899.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4450
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      29.41

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.662
_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    0.158
_shelx_estimated_absorpt_T_min   0.941
_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      200(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            7961
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_av_R_equivalents  0.0485
_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       27
_diffrn_reflns_theta_min         2.034
_diffrn_reflns_theta_max         29.244
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2433
_reflns_number_gt                1375
_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)+(0.0522P)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       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2433
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      0.939
_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 0.7606(3) 0.12101(13) 0.56474(6) 0.0248(3) Uani 1 1 d . . . . .
H6 H 0.573(5) 0.133(2) 0.5436(10) 0.030 Uiso 1 1 d . U . . .
O3 O 0.5977(3) 0.35486(14) 0.43295(7) 0.0302(3) Uani 1 1 d . . . . .
H3 H 0.458(5) 0.361(2) 0.3945(11) 0.036 Uiso 1 1 d . U . . .
O5 O 1.2189(3) 0.14511(14) 0.49334(7) 0.0276(3) Uani 1 1 d . . . . .
H5 H 1.145(5) 0.074(2) 0.4700(11) 0.033 Uiso 1 1 d . U . . .
O8 O 1.2209(3) 0.15948(14) 0.66260(6) 0.0302(3) Uani 1 1 d . . . . .
O7 O 1.3263(3) 0.36565(14) 0.61650(7) 0.0328(3) Uani 1 1 d . . . . .
H7 H 1.4645 0.3670 0.6496 0.039 Uiso 1 1 calc R U . . .
O4 O 0.7456(3) 0.14746(14) 0.39553(6) 0.0307(3) Uani 1 1 d . . . . .
O1 O 1.2252(3) 0.58531(13) 0.29313(6) 0.0287(3) Uani 1 1 d . . . . .
C3 C 0.7716(4) 0.24717(18) 0.43505(8) 0.0225(4) Uani 1 1 d . . . . .
O2 O 1.1800(3) 0.36230(14) 0.33154(7) 0.0334(3) Uani 1 1 d . . . . .
C5 C 0.9164(4) 0.24869(19) 0.56078(8) 0.0217(4) Uani 1 1 d . . . . .
H5A H 0.802(4) 0.333(2) 0.5630(9) 0.026 Uiso 1 1 d . U . . .
C2 C 1.0997(4) 0.46728(18) 0.29346(8) 0.0226(4) Uani 1 1 d . . . . .
C6 C 1.1706(4) 0.25132(18) 0.61959(8) 0.0225(4) Uani 1 1 d . . . . .
C4 C 1.0197(4) 0.25619(19) 0.49498(9) 0.0231(4) Uani 1 1 d . . . . .
H4 H 1.112(4) 0.348(2) 0.4933(10) 0.028 Uiso 1 1 d . U . . .
N1 N 0.7950(4) 0.54900(18) 0.18689(8) 0.0275(4) Uani 1 1 d . . . . .
H1A H 0.607(5) 0.566(2) 0.1633(11) 0.041 Uiso 1 1 d . U . . .
H1B H 0.858(5) 0.635(3) 0.2012(11) 0.041 Uiso 1 1 d . U . . .
H1C H 0.897(5) 0.508(2) 0.1591(11) 0.041 Uiso 1 1 d . U . . .
C1 C 0.8175(4) 0.4498(2) 0.24431(9) 0.0250(4) Uani 1 1 d . . . . .
H1D H 0.664(4) 0.475(2) 0.2652(10) 0.030 Uiso 1 1 d . U . . .
H1E H 0.787(4) 0.352(2) 0.2268(10) 0.030 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 1.418(2) . ?
O6 H6 0.92(2) . ?
O3 C3 1.302(2) . ?
O3 H3 0.92(2) . ?
O5 C4 1.418(2) . ?
O5 H5 0.85(2) . ?
O8 C6 1.214(2) . ?
O7 C6 1.313(2) . ?
O7 H7 0.8400 . ?
O4 C3 1.221(2) . ?
O1 C2 1.255(2) . ?
C3 C4 1.517(2) . ?
O2 C2 1.258(2) . ?
C5 C6 1.518(2) . ?
C5 C4 1.543(2) . ?
C5 H5A 0.97(2) . ?
C2 C1 1.513(3) . ?
C4 H4 0.97(2) . ?
N1 C1 1.482(2) . ?
N1 H1A 0.94(2) . ?
N1 H1B 0.89(2) . ?
N1 H1C 0.92(2) . ?
C1 H1D 0.96(2) . ?
C1 H1E 0.97(2) . ?

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 110.4(13) . . ?
C3 O3 H3 114.8(13) . . ?
C4 O5 H5 112.3(15) . . ?
C6 O7 H7 109.5 . . ?
O4 C3 O3 126.37(17) . . ?
O4 C3 C4 121.83(15) . . ?
O3 C3 C4 111.79(15) . . ?
O6 C5 C6 108.23(14) . . ?
O6 C5 C4 111.53(14) . . ?
C6 C5 C4 109.53(14) . . ?
O6 C5 H5A 111.1(12) . . ?
C6 C5 H5A 108.6(12) . . ?
C4 C5 H5A 107.8(11) . . ?
O1 C2 O2 126.95(17) . . ?
O1 C2 C1 117.02(15) . . ?
O2 C2 C1 116.01(15) . . ?
O8 C6 O7 125.59(17) . . ?
O8 C6 C5 124.23(16) . . ?
O7 C6 C5 110.18(14) . . ?
O5 C4 C3 110.96(14) . . ?
O5 C4 C5 109.94(14) . . ?
C3 C4 C5 110.93(14) . . ?
O5 C4 H4 108.7(12) . . ?
C3 C4 H4 108.0(12) . . ?
C5 C4 H4 108.3(12) . . ?
C1 N1 H1A 113.9(13) . . ?
C1 N1 H1B 110.0(15) . . ?
H1A N1 H1B 104(2) . . ?
C1 N1 H1C 106.3(14) . . ?
H1A N1 H1C 109.8(19) . . ?
H1B N1 H1C 113(2) . . ?
N1 C1 C2 111.08(15) . . ?
N1 C1 H1D 106.2(12) . . ?
C2 C1 H1D 110.1(12) . . ?
N1 C1 H1E 107.9(12) . . ?
C2 C1 H1E 112.8(12) . . ?
H1D C1 H1E 108.6(17) . . ?

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 -1.7(2) . . . . ?
C4 C5 C6 O8 -123.47(18) . . . . ?
O6 C5 C6 O7 177.80(14) . . . . ?
C4 C5 C6 O7 56.01(19) . . . . ?
O4 C3 C4 O5 6.0(2) . . . . ?
O3 C3 C4 O5 -174.97(14) . . . . ?
O4 C3 C4 C5 -116.50(18) . . . . ?
O3 C3 C4 C5 62.51(18) . . . . ?
O6 C5 C4 O5 -65.40(18) . . . . ?
C6 C5 C4 O5 54.39(18) . . . . ?
O6 C5 C4 C3 57.72(18) . . . . ?
C6 C5 C4 C3 177.50(14) . . . . ?
O1 C2 C1 N1 23.5(2) . . . . ?
O2 C2 C1 N1 -158.21(15) . . . . ?

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) 1.79(2) 2.7079(18) 172.7(19) 1_455
O3 H3 O2 0.92(2) 1.64(2) 2.5575(19) 172(2) 1_455
O5 H5 O6 0.85(2) 2.04(2) 2.7606(18) 143(2) 3_756
O7 H7 O1 0.84 1.74 2.5597(19) 163.4 3_866
N1 H1C O6 0.92(2) 2.25(2) 2.939(2) 131.7(18) 4_565
N1 H1C O8 0.92(2) 2.20(2) 2.949(2) 138.8(18) 4_565
N1 H1A O4 0.94(2) 2.01(2) 2.924(2) 165(2) 2_655
N1 H1B O2 0.89(2) 2.21(2) 2.947(2) 140(2) 2_755

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_gta175K
_database_code_depnum_ccdc_archive 'CCDC 1437086'
_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                   4.8221(6)
_cell_length_b                   9.3052(9)
_cell_length_c                   20.493(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.666(10)
_cell_angle_gamma                90
_cell_volume                     897.16(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    175(2)
_cell_measurement_reflns_used    4809
_cell_measurement_theta_min      2.07
_cell_measurement_theta_max      29.42

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.667
_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    0.158
_shelx_estimated_absorpt_T_min   0.941
_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      175(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            7941
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_av_R_equivalents  0.0482
_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       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.037
_diffrn_reflns_theta_max         29.242
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2436
_reflns_number_gt                1421
_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)+(0.0606P)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       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2436
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_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 0.7609(3) 0.12072(14) 0.56483(7) 0.0233(3) Uani 1 1 d . . . . .
H6 H 0.575(5) 0.131(2) 0.5426(11) 0.028 Uiso 1 1 d . U . . .
O3 O 0.5989(3) 0.35502(14) 0.43284(7) 0.0277(3) Uani 1 1 d . . . . .
H3 H 0.454(5) 0.361(2) 0.3923(12) 0.033 Uiso 1 1 d . U . . .
O5 O 1.2204(3) 0.14538(15) 0.49319(7) 0.0258(3) Uani 1 1 d . . . . .
H5 H 1.150(5) 0.075(3) 0.4694(12) 0.031 Uiso 1 1 d . U . . .
O8 O 1.2214(3) 0.15870(15) 0.66275(7) 0.0278(3) Uani 1 1 d . . . . .
O7 O 1.3267(3) 0.36525(15) 0.61660(7) 0.0299(3) Uani 1 1 d . . . . .
H7 H 1.4646 0.3667 0.6497 0.036 Uiso 1 1 calc R U . . .
O4 O 0.7469(3) 0.14710(15) 0.39551(7) 0.0279(3) Uani 1 1 d . . . . .
O1 O 1.2239(3) 0.58579(14) 0.29336(7) 0.0263(3) Uani 1 1 d . . . . .
C3 C 0.7723(4) 0.24700(19) 0.43503(9) 0.0212(4) Uani 1 1 d . . . . .
O2 O 1.1801(3) 0.36232(15) 0.33154(7) 0.0307(3) Uani 1 1 d . . . . .
C5 C 0.9172(4) 0.2482(2) 0.56098(9) 0.0203(4) Uani 1 1 d . . . . .
H5A H 0.803(5) 0.331(2) 0.5631(10) 0.024 Uiso 1 1 d . U . . .
C2 C 1.0988(4) 0.46743(19) 0.29357(9) 0.0208(4) Uani 1 1 d . . . . .
C6 C 1.1710(4) 0.25081(19) 0.61972(9) 0.0210(4) Uani 1 1 d . . . . .
C4 C 1.0206(4) 0.2562(2) 0.49480(9) 0.0220(4) Uani 1 1 d . . . . .
H4 H 1.111(5) 0.349(2) 0.4919(11) 0.026 Uiso 1 1 d . U . . .
N1 N 0.7935(4) 0.54924(18) 0.18692(8) 0.0250(4) Uani 1 1 d . . . . .
H1A H 0.597(5) 0.566(3) 0.1628(12) 0.038 Uiso 1 1 d . U . . .
H1B H 0.854(5) 0.633(3) 0.2010(12) 0.038 Uiso 1 1 d . U . . .
H1C H 0.896(5) 0.511(3) 0.1593(11) 0.038 Uiso 1 1 d . U . . .
C1 C 0.8167(4) 0.4499(2) 0.24447(9) 0.0232(4) Uani 1 1 d . . . . .
H1D H 0.664(5) 0.473(2) 0.2658(11) 0.028 Uiso 1 1 d . U . . .
H1E H 0.789(5) 0.354(2) 0.2274(11) 0.028 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 1.417(2) . ?
O6 H6 0.92(2) . ?
O3 C3 1.302(2) . ?
O3 H3 0.96(2) . ?
O5 C4 1.417(2) . ?
O5 H5 0.85(2) . ?
O8 C6 1.215(2) . ?
O7 C6 1.313(2) . ?
O7 H7 0.8400 . ?
O4 C3 1.221(2) . ?
O1 C2 1.256(2) . ?
C3 C4 1.516(3) . ?
O2 C2 1.258(2) . ?
C5 C6 1.517(3) . ?
C5 C4 1.546(2) . ?
C5 H5A 0.96(2) . ?
C2 C1 1.513(3) . ?
C4 H4 0.97(2) . ?
N1 C1 1.483(2) . ?
N1 H1A 0.98(3) . ?
N1 H1B 0.86(3) . ?
N1 H1C 0.91(2) . ?
C1 H1D 0.96(2) . ?
C1 H1E 0.96(2) . ?

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 110.9(14) . . ?
C3 O3 H3 114.3(13) . . ?
C4 O5 H5 113.0(16) . . ?
C6 O7 H7 109.5 . . ?
O4 C3 O3 126.48(18) . . ?
O4 C3 C4 121.69(16) . . ?
O3 C3 C4 111.82(15) . . ?
O6 C5 C6 108.40(14) . . ?
O6 C5 C4 111.55(14) . . ?
C6 C5 C4 109.64(15) . . ?
O6 C5 H5A 110.9(13) . . ?
C6 C5 H5A 108.8(13) . . ?
C4 C5 H5A 107.5(12) . . ?
O1 C2 O2 126.81(18) . . ?
O1 C2 C1 117.02(16) . . ?
O2 C2 C1 116.14(16) . . ?
O8 C6 O7 125.59(18) . . ?
O8 C6 C5 124.23(16) . . ?
O7 C6 C5 110.18(15) . . ?
O5 C4 C3 111.14(15) . . ?
O5 C4 C5 109.70(15) . . ?
C3 C4 C5 110.88(15) . . ?
O5 C4 H4 109.0(13) . . ?
C3 C4 H4 106.6(13) . . ?
C5 C4 H4 109.4(12) . . ?
C1 N1 H1A 113.4(14) . . ?
C1 N1 H1B 109.8(16) . . ?
H1A N1 H1B 104(2) . . ?
C1 N1 H1C 107.0(15) . . ?
H1A N1 H1C 110(2) . . ?
H1B N1 H1C 112(2) . . ?
N1 C1 C2 111.23(15) . . ?
N1 C1 H1D 107.1(13) . . ?
C2 C1 H1D 110.0(13) . . ?
N1 C1 H1E 108.2(13) . . ?
C2 C1 H1E 112.1(14) . . ?
H1D C1 H1E 108.1(18) . . ?

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 -1.5(2) . . . . ?
C4 C5 C6 O8 -123.51(18) . . . . ?
O6 C5 C6 O7 177.86(14) . . . . ?
C4 C5 C6 O7 55.9(2) . . . . ?
O4 C3 C4 O5 5.9(2) . . . . ?
O3 C3 C4 O5 -174.67(14) . . . . ?
O4 C3 C4 C5 -116.35(18) . . . . ?
O3 C3 C4 C5 63.04(19) . . . . ?
O6 C5 C4 O5 -65.79(19) . . . . ?
C6 C5 C4 O5 54.30(19) . . . . ?
O6 C5 C4 C3 57.34(19) . . . . ?
C6 C5 C4 C3 177.44(15) . . . . ?
O1 C2 C1 N1 23.6(2) . . . . ?
O2 C2 C1 N1 -158.02(16) . . . . ?

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) 1.79(3) 2.706(2) 175(2) 1_455
O3 H3 O2 0.96(2) 1.60(2) 2.560(2) 171(2) 1_455
O5 H5 O6 0.85(2) 2.03(2) 2.7568(19) 144(2) 3_756
O7 H7 O1 0.84 1.74 2.560(2) 163.2 3_866
N1 H1C O6 0.91(2) 2.26(2) 2.935(2) 131(2) 4_565
N1 H1C O8 0.91(2) 2.21(2) 2.949(2) 138.1(19) 4_565
N1 H1A O4 0.98(3) 1.97(3) 2.923(2) 164(2) 2_655
N1 H1B O2 0.86(3) 2.23(3) 2.944(2) 140(2) 2_755

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_gta150K
_database_code_depnum_ccdc_archive 'CCDC 1437087'
_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                   4.8165(6)
_cell_length_b                   9.3035(8)
_cell_length_c                   20.450(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.500(10)
_cell_angle_gamma                90
_cell_volume                     894.65(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5063
_cell_measurement_theta_min      2.06
_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    1.672
_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    0.159
_shelx_estimated_absorpt_T_min   0.941
_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      150(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            7910
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0483
_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       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.040
_diffrn_reflns_theta_max         29.255
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2419
_reflns_number_gt                1475
_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)+(0.0542P)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       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2419
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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 0.7612(3) 0.12045(12) 0.56489(6) 0.0199(3) Uani 1 1 d . . . . .
H6 H 0.578(5) 0.134(2) 0.5431(10) 0.024 Uiso 1 1 d . U . . .
O3 O 0.5999(3) 0.35539(13) 0.43280(6) 0.0242(3) Uani 1 1 d . . . . .
H3 H 0.465(5) 0.358(2) 0.3958(11) 0.029 Uiso 1 1 d . U . . .
O5 O 1.2221(3) 0.14527(14) 0.49296(6) 0.0225(3) Uani 1 1 d . . . . .
H5 H 1.147(5) 0.075(2) 0.4696(11) 0.027 Uiso 1 1 d . U . . .
O8 O 1.2212(3) 0.15802(13) 0.66279(6) 0.0237(3) Uani 1 1 d . . . . .
O7 O 1.3279(3) 0.36502(14) 0.61666(6) 0.0259(3) Uani 1 1 d . . . . .
H7 H 1.4673 0.3656 0.6494 0.031 Uiso 1 1 calc R U . . .
O4 O 0.7476(3) 0.14680(14) 0.39540(6) 0.0242(3) Uani 1 1 d . . . . .
O1 O 1.2230(3) 0.58665(13) 0.29339(6) 0.0228(3) Uani 1 1 d . . . . .
C3 C 0.7735(4) 0.24698(18) 0.43489(8) 0.0188(4) Uani 1 1 d . . . . .
O2 O 1.1807(3) 0.36251(14) 0.33155(6) 0.0262(3) Uani 1 1 d . . . . .
C5 C 0.9179(4) 0.24826(18) 0.56093(8) 0.0178(3) Uani 1 1 d . . . . .
H5A H 0.807(4) 0.332(2) 0.5642(10) 0.021 Uiso 1 1 d . U . . .
C2 C 1.0988(4) 0.46765(18) 0.29361(8) 0.0189(3) Uani 1 1 d . . . . .
C6 C 1.1721(4) 0.25039(18) 0.61969(8) 0.0185(3) Uani 1 1 d . . . . .
C4 C 1.0224(4) 0.25625(19) 0.49479(8) 0.0195(4) Uani 1 1 d . . . . .
H4 H 1.114(4) 0.349(2) 0.4922(10) 0.023 Uiso 1 1 d . U . . .
N1 N 0.7933(3) 0.54935(17) 0.18706(8) 0.0221(3) Uani 1 1 d . . . . .
H1A H 0.606(5) 0.564(2) 0.1640(11) 0.033 Uiso 1 1 d . U . . .
H1B H 0.856(5) 0.638(3) 0.2011(11) 0.033 Uiso 1 1 d . U . . .
H1C H 0.897(5) 0.511(2) 0.1589(11) 0.033 Uiso 1 1 d . U . . .
C1 C 0.8162(4) 0.44976(19) 0.24470(9) 0.0207(4) Uani 1 1 d . . . . .
H1D H 0.663(4) 0.473(2) 0.2661(10) 0.025 Uiso 1 1 d . U . . .
H1E H 0.784(4) 0.350(2) 0.2280(11) 0.025 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 1.420(2) . ?
O6 H6 0.91(2) . ?
O3 C3 1.305(2) . ?
O3 H3 0.89(2) . ?
O5 C4 1.417(2) . ?
O5 H5 0.85(2) . ?
O8 C6 1.217(2) . ?
O7 C6 1.313(2) . ?
O7 H7 0.8400 . ?
O4 C3 1.222(2) . ?
O1 C2 1.259(2) . ?
C3 C4 1.520(2) . ?
O2 C2 1.258(2) . ?
C5 C6 1.519(2) . ?
C5 C4 1.544(2) . ?
C5 H5A 0.96(2) . ?
C2 C1 1.514(3) . ?
C4 H4 0.97(2) . ?
N1 C1 1.485(2) . ?
N1 H1A 0.93(2) . ?
N1 H1B 0.90(2) . ?
N1 H1C 0.91(2) . ?
C1 H1D 0.96(2) . ?
C1 H1E 0.99(2) . ?

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 109.2(13) . . ?
C3 O3 H3 113.2(14) . . ?
C4 O5 H5 111.9(15) . . ?
C6 O7 H7 109.5 . . ?
O4 C3 O3 126.51(16) . . ?
O4 C3 C4 121.72(15) . . ?
O3 C3 C4 111.76(14) . . ?
O6 C5 C6 108.26(13) . . ?
O6 C5 C4 111.62(13) . . ?
C6 C5 C4 109.44(14) . . ?
O6 C5 H5A 111.6(12) . . ?
C6 C5 H5A 107.5(13) . . ?
C4 C5 H5A 108.3(11) . . ?
O2 C2 O1 126.91(17) . . ?
O2 C2 C1 116.04(15) . . ?
O1 C2 C1 117.02(15) . . ?
O8 C6 O7 125.75(16) . . ?
O8 C6 C5 124.12(15) . . ?
O7 C6 C5 110.14(14) . . ?
O5 C4 C3 111.03(14) . . ?
O5 C4 C5 109.87(14) . . ?
C3 C4 C5 110.70(14) . . ?
O5 C4 H4 109.0(12) . . ?
C3 C4 H4 107.0(13) . . ?
C5 C4 H4 109.1(12) . . ?
C1 N1 H1A 113.1(13) . . ?
C1 N1 H1B 110.7(14) . . ?
H1A N1 H1B 104(2) . . ?
C1 N1 H1C 107.7(14) . . ?
H1A N1 H1C 109.9(19) . . ?
H1B N1 H1C 111(2) . . ?
N1 C1 C2 110.94(14) . . ?
N1 C1 H1D 106.6(12) . . ?
C2 C1 H1D 110.1(12) . . ?
N1 C1 H1E 109.4(12) . . ?
C2 C1 H1E 112.5(12) . . ?
H1D C1 H1E 107.1(17) . . ?

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 -1.8(2) . . . . ?
C4 C5 C6 O8 -123.66(17) . . . . ?
O6 C5 C6 O7 178.03(13) . . . . ?
C4 C5 C6 O7 56.17(18) . . . . ?
O4 C3 C4 O5 6.2(2) . . . . ?
O3 C3 C4 O5 -174.60(13) . . . . ?
O4 C3 C4 C5 -116.14(17) . . . . ?
O3 C3 C4 C5 63.09(18) . . . . ?
O6 C5 C4 O5 -65.57(18) . . . . ?
C6 C5 C4 O5 54.25(18) . . . . ?
O6 C5 C4 C3 57.42(18) . . . . ?
C6 C5 C4 C3 177.24(13) . . . . ?
O2 C2 C1 N1 -157.95(14) . . . . ?
O1 C2 C1 N1 23.9(2) . . . . ?

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 0.91(2) 1.80(2) 2.7030(18) 173.4(19) 1_455
O3 H3 O2 0.89(2) 1.68(2) 2.5613(19) 173(2) 1_455
O5 H5 O6 0.85(2) 2.03(2) 2.7493(17) 142(2) 3_756
O7 H7 O1 0.84 1.74 2.5580(18) 163.3 3_866
N1 H1C O6 0.91(2) 2.26(2) 2.932(2) 130.7(18) 4_565
N1 H1C O8 0.91(2) 2.21(2) 2.943(2) 137.2(18) 4_565
N1 H1A O4 0.93(2) 2.02(2) 2.924(2) 163(2) 2_655
N1 H1B O2 0.90(2) 2.19(2) 2.944(2) 140.6(19) 2_755

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_gta125K
_database_code_depnum_ccdc_archive 'CCDC 1437088'
_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                   4.8107(6)
_cell_length_b                   9.3013(8)
_cell_length_c                   20.411(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.337(10)
_cell_angle_gamma                90
_cell_volume                     892.23(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    5254
_cell_measurement_theta_min      2.04
_cell_measurement_theta_max      29.41

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.676
_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    0.159
_shelx_estimated_absorpt_T_min   0.940
_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      125(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            7901
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0483
_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       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.043
_diffrn_reflns_theta_max         29.200
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2412
_reflns_number_gt                1516
_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)+(0.0580P)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       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2412
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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 0.7617(3) 0.12027(13) 0.56491(6) 0.0184(3) Uani 1 1 d . . . . .
H6 H 0.579(5) 0.132(2) 0.5429(11) 0.022 Uiso 1 1 d . U . . .
O3 O 0.6013(3) 0.35562(13) 0.43276(6) 0.0216(3) Uani 1 1 d . . . . .
H3 H 0.458(5) 0.357(2) 0.3955(11) 0.026 Uiso 1 1 d . U . . .
O5 O 1.2235(3) 0.14547(14) 0.49276(6) 0.0206(3) Uani 1 1 d . . . . .
H5 H 1.148(5) 0.076(2) 0.4701(11) 0.025 Uiso 1 1 d . U . . .
O8 O 1.2214(3) 0.15743(13) 0.66294(6) 0.0210(3) Uani 1 1 d . . . . .
O7 O 1.3285(3) 0.36470(14) 0.61669(6) 0.0233(3) Uani 1 1 d . . . . .
H7 H 1.4675 0.3655 0.6495 0.028 Uiso 1 1 calc R U . . .
O4 O 0.7488(3) 0.14639(14) 0.39531(6) 0.0221(3) Uani 1 1 d . . . . .
O1 O 1.2221(3) 0.58707(13) 0.29348(6) 0.0207(3) Uani 1 1 d . . . . .
C3 C 0.7745(4) 0.24717(18) 0.43470(8) 0.0176(4) Uani 1 1 d . . . . .
O2 O 1.1808(3) 0.36234(14) 0.33164(6) 0.0237(3) Uani 1 1 d . . . . .
C5 C 0.9179(4) 0.24815(18) 0.56115(8) 0.0165(3) Uani 1 1 d . . . . .
H5A H 0.804(5) 0.334(2) 0.5634(10) 0.020 Uiso 1 1 d . U . . .
C2 C 1.0986(4) 0.46777(18) 0.29371(8) 0.0169(3) Uani 1 1 d . . . . .
C6 C 1.1721(4) 0.25019(18) 0.61997(8) 0.0170(4) Uani 1 1 d . . . . .
C4 C 1.0234(4) 0.25641(19) 0.49464(8) 0.0175(4) Uani 1 1 d . . . . .
H4 H 1.114(5) 0.347(2) 0.4927(10) 0.021 Uiso 1 1 d . U . . .
N1 N 0.7918(4) 0.54982(17) 0.18712(8) 0.0200(3) Uani 1 1 d . . . . .
H1A H 0.600(5) 0.566(2) 0.1638(11) 0.030 Uiso 1 1 d . U . . .
H1B H 0.850(5) 0.636(3) 0.2018(11) 0.030 Uiso 1 1 d . U . . .
H1C H 0.898(5) 0.510(2) 0.1606(11) 0.030 Uiso 1 1 d . U . . .
C1 C 0.8157(4) 0.44970(19) 0.24493(9) 0.0184(4) Uani 1 1 d . . . . .
H1D H 0.661(5) 0.473(2) 0.2664(10) 0.022 Uiso 1 1 d . U . . .
H1E H 0.787(5) 0.352(2) 0.2278(11) 0.022 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 1.418(2) . ?
O6 H6 0.90(2) . ?
O3 C3 1.304(2) . ?
O3 H3 0.91(2) . ?
O5 C4 1.417(2) . ?
O5 H5 0.83(2) . ?
O8 C6 1.217(2) . ?
O7 C6 1.314(2) . ?
O7 H7 0.8400 . ?
O4 C3 1.224(2) . ?
O1 C2 1.259(2) . ?
C3 C4 1.520(2) . ?
O2 C2 1.260(2) . ?
C5 C6 1.520(3) . ?
C5 C4 1.549(2) . ?
C5 H5A 0.97(2) . ?
C2 C1 1.514(3) . ?
C4 H4 0.96(2) . ?
N1 C1 1.488(2) . ?
N1 H1A 0.95(2) . ?
N1 H1B 0.88(2) . ?
N1 H1C 0.90(2) . ?
C1 H1D 0.96(2) . ?
C1 H1E 0.97(2) . ?

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 109.7(14) . . ?
C3 O3 H3 113.6(14) . . ?
C4 O5 H5 111.4(16) . . ?
C6 O7 H7 109.5 . . ?
O4 C3 O3 126.75(17) . . ?
O4 C3 C4 121.58(15) . . ?
O3 C3 C4 111.67(14) . . ?
O6 C5 C6 108.30(13) . . ?
O6 C5 C4 111.45(14) . . ?
C6 C5 C4 109.44(14) . . ?
O6 C5 H5A 112.0(12) . . ?
C6 C5 H5A 108.6(13) . . ?
C4 C5 H5A 107.0(12) . . ?
O1 C2 O2 127.00(17) . . ?
O1 C2 C1 117.00(15) . . ?
O2 C2 C1 115.97(15) . . ?
O8 C6 O7 125.87(17) . . ?
O8 C6 C5 124.08(15) . . ?
O7 C6 C5 110.04(14) . . ?
O5 C4 C3 111.08(14) . . ?
O5 C4 C5 109.82(14) . . ?
C3 C4 C5 110.68(14) . . ?
O5 C4 H4 109.1(13) . . ?
C3 C4 H4 107.6(13) . . ?
C5 C4 H4 108.5(12) . . ?
C1 N1 H1A 113.5(13) . . ?
C1 N1 H1B 109.7(15) . . ?
H1A N1 H1B 103(2) . . ?
C1 N1 H1C 105.1(14) . . ?
H1A N1 H1C 112.3(19) . . ?
H1B N1 H1C 113(2) . . ?
N1 C1 C2 111.00(14) . . ?
N1 C1 H1D 106.6(12) . . ?
C2 C1 H1D 110.4(13) . . ?
N1 C1 H1E 108.5(13) . . ?
C2 C1 H1E 112.4(13) . . ?
H1D C1 H1E 107.7(18) . . ?

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 -1.8(2) . . . . ?
C4 C5 C6 O8 -123.43(17) . . . . ?
O6 C5 C6 O7 177.55(13) . . . . ?
C4 C5 C6 O7 55.87(18) . . . . ?
O4 C3 C4 O5 6.5(2) . . . . ?
O3 C3 C4 O5 -174.54(13) . . . . ?
O4 C3 C4 C5 -115.77(17) . . . . ?
O3 C3 C4 C5 63.19(18) . . . . ?
O6 C5 C4 O5 -65.55(18) . . . . ?
C6 C5 C4 O5 54.21(18) . . . . ?
O6 C5 C4 C3 57.46(18) . . . . ?
C6 C5 C4 C3 177.22(14) . . . . ?
O1 C2 C1 N1 23.9(2) . . . . ?
O2 C2 C1 N1 -158.05(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 0.90(2) 1.80(2) 2.7016(19) 174(2) 1_455
O3 H3 O2 0.91(2) 1.65(2) 2.5634(19) 175(2) 1_455
O5 H5 O6 0.83(2) 2.04(2) 2.7452(18) 142(2) 3_756
O7 H7 O1 0.84 1.74 2.5579(19) 163.3 3_866
N1 H1C O6 0.90(2) 2.27(2) 2.931(2) 129.6(18) 4_565
N1 H1C O8 0.90(2) 2.19(2) 2.944(2) 140.4(19) 4_565
N1 H1A O4 0.95(2) 1.99(2) 2.921(2) 164(2) 2_655
N1 H1B O2 0.88(2) 2.20(2) 2.939(2) 140(2) 2_755

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_gta100K
_database_code_depnum_ccdc_archive 'CCDC 1437089'
_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                   4.8067(6)
_cell_length_b                   9.3033(8)
_cell_length_c                   20.367(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.159(10)
_cell_angle_gamma                90
_cell_volume                     890.34(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5463
_cell_measurement_theta_min      2.06
_cell_measurement_theta_max      29.43

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.680
_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    0.160
_shelx_estimated_absorpt_T_min   0.940
_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      100(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            7889
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_av_R_equivalents  0.0481
_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       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.046
_diffrn_reflns_theta_max         29.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2408
_reflns_number_gt                1544
_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)+(0.0665P)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         2408
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.7619(3) 0.12017(14) 0.56498(7) 0.0171(3) Uani 1 1 d . . . . .
H6 H 0.580(6) 0.131(2) 0.5435(12) 0.021 Uiso 1 1 d . U . . .
O3 O 0.6025(3) 0.35599(14) 0.43266(7) 0.0197(3) Uani 1 1 d . . . . .
H3 H 0.458(5) 0.359(3) 0.3947(12) 0.024 Uiso 1 1 d . U . . .
O5 O 1.2249(3) 0.14561(15) 0.49246(7) 0.0189(3) Uani 1 1 d . . . . .
H5 H 1.152(5) 0.074(3) 0.4707(12) 0.023 Uiso 1 1 d . U . . .
O8 O 1.2219(3) 0.15674(14) 0.66289(7) 0.0195(3) Uani 1 1 d . . . . .
O7 O 1.3292(3) 0.36436(15) 0.61678(7) 0.0204(3) Uani 1 1 d . . . . .
H7 H 1.4705 0.3639 0.6491 0.024 Uiso 1 1 calc R U . . .
O4 O 0.7497(3) 0.14626(15) 0.39527(7) 0.0197(3) Uani 1 1 d . . . . .
O1 O 1.2211(3) 0.58764(14) 0.29355(7) 0.0188(3) Uani 1 1 d . . . . .
C3 C 0.7754(4) 0.24706(19) 0.43462(9) 0.0164(4) Uani 1 1 d . . . . .
O2 O 1.1816(3) 0.36244(15) 0.33171(7) 0.0212(3) Uani 1 1 d . . . . .
C5 C 0.9189(4) 0.2478(2) 0.56112(9) 0.0148(4) Uani 1 1 d . . . . .
H5A H 0.807(5) 0.332(2) 0.5645(11) 0.018 Uiso 1 1 d . U . . .
C2 C 1.0984(4) 0.46803(19) 0.29385(9) 0.0158(4) Uani 1 1 d . . . . .
C6 C 1.1733(4) 0.24956(19) 0.61990(9) 0.0155(4) Uani 1 1 d . . . . .
C4 C 1.0241(4) 0.2564(2) 0.49447(9) 0.0160(4) Uani 1 1 d . . . . .
H4 H 1.112(5) 0.347(3) 0.4921(11) 0.019 Uiso 1 1 d . U . . .
N1 N 0.7916(4) 0.54982(18) 0.18724(8) 0.0181(4) Uani 1 1 d . . . . .
H1A H 0.599(5) 0.569(3) 0.1643(12) 0.027 Uiso 1 1 d . U . . .
H1B H 0.847(6) 0.636(3) 0.2014(12) 0.027 Uiso 1 1 d . U . . .
H1C H 0.901(5) 0.511(3) 0.1594(12) 0.027 Uiso 1 1 d . U . . .
C1 C 0.8152(4) 0.4497(2) 0.24496(9) 0.0177(4) Uani 1 1 d . . . . .
H1D H 0.667(5) 0.471(2) 0.2669(11) 0.021 Uiso 1 1 d . U . . .
H1E H 0.785(5) 0.351(3) 0.2285(12) 0.021 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 1.418(2) . ?
O6 H6 0.90(3) . ?
O3 C3 1.306(2) . ?
O3 H3 0.92(3) . ?
O5 C4 1.419(2) . ?
O5 H5 0.84(3) . ?
O8 C6 1.217(2) . ?
O7 C6 1.314(2) . ?
O7 H7 0.8400 . ?
O4 C3 1.223(2) . ?
O1 C2 1.260(2) . ?
C3 C4 1.519(3) . ?
O2 C2 1.261(2) . ?
C5 C6 1.520(3) . ?
C5 C4 1.547(2) . ?
C5 H5A 0.96(2) . ?
C2 C1 1.517(3) . ?
C4 H4 0.95(2) . ?
N1 C1 1.486(2) . ?
N1 H1A 0.96(3) . ?
N1 H1B 0.88(3) . ?
N1 H1C 0.92(2) . ?
C1 H1D 0.94(2) . ?
C1 H1E 0.98(2) . ?

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 110.8(15) . . ?
C3 O3 H3 114.2(15) . . ?
C4 O5 H5 112.4(17) . . ?
C6 O7 H7 109.5 . . ?
O4 C3 O3 126.82(18) . . ?
O4 C3 C4 121.56(16) . . ?
O3 C3 C4 111.61(15) . . ?
O6 C5 C6 108.33(14) . . ?
O6 C5 C4 111.59(14) . . ?
C6 C5 C4 109.47(15) . . ?
O6 C5 H5A 111.4(14) . . ?
C6 C5 H5A 107.8(14) . . ?
C4 C5 H5A 108.2(13) . . ?
O1 C2 O2 127.03(18) . . ?
O1 C2 C1 116.91(16) . . ?
O2 C2 C1 116.04(16) . . ?
O8 C6 O7 125.92(18) . . ?
O8 C6 C5 124.03(17) . . ?
O7 C6 C5 110.05(15) . . ?
O5 C4 C3 111.13(15) . . ?
O5 C4 C5 109.75(15) . . ?
C3 C4 C5 110.72(15) . . ?
O5 C4 H4 109.4(14) . . ?
C3 C4 H4 107.0(15) . . ?
C5 C4 H4 108.8(13) . . ?
C1 N1 H1A 114.2(14) . . ?
C1 N1 H1B 110.4(16) . . ?
H1A N1 H1B 100(2) . . ?
C1 N1 H1C 106.3(15) . . ?
H1A N1 H1C 113(2) . . ?
H1B N1 H1C 113(2) . . ?
N1 C1 C2 110.93(15) . . ?
N1 C1 H1D 107.6(14) . . ?
C2 C1 H1D 109.2(14) . . ?
N1 C1 H1E 109.7(14) . . ?
C2 C1 H1E 112.2(14) . . ?
H1D C1 H1E 107(2) . . ?

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 -1.7(2) . . . . ?
C4 C5 C6 O8 -123.64(18) . . . . ?
O6 C5 C6 O7 178.01(14) . . . . ?
C4 C5 C6 O7 56.12(19) . . . . ?
O4 C3 C4 O5 6.7(2) . . . . ?
O3 C3 C4 O5 -174.17(14) . . . . ?
O4 C3 C4 C5 -115.54(18) . . . . ?
O3 C3 C4 C5 63.59(19) . . . . ?
O6 C5 C4 O5 -65.88(19) . . . . ?
C6 C5 C4 O5 54.03(19) . . . . ?
O6 C5 C4 C3 57.16(19) . . . . ?
C6 C5 C4 C3 177.07(15) . . . . ?
O1 C2 C1 N1 23.9(2) . . . . ?
O2 C2 C1 N1 -157.86(15) . . . . ?

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 0.90(3) 1.81(3) 2.701(2) 174(2) 1_455
O3 H3 O2 0.92(3) 1.64(3) 2.564(2) 175(2) 1_455
O5 H5 O6 0.84(3) 2.02(2) 2.7419(19) 144(2) 3_756
O7 H7 O1 0.84 1.74 2.558(2) 163.1 3_866
N1 H1C O6 0.92(2) 2.26(2) 2.928(2) 129(2) 4_565
N1 H1C O8 0.92(2) 2.19(3) 2.941(2) 139(2) 4_565
N1 H1A O4 0.96(3) 1.99(3) 2.925(2) 165(2) 2_655
N1 H1B O2 0.88(3) 2.21(3) 2.940(2) 141(2) 2_755

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.092

