# 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_gph293K
_database_code_depnum_ccdc_archive 'CCDC 1437185'
_audit_update_record             
;
2016-06-01 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-phthalic acid (1:1)'
_chemical_name_common            'glycine-phthalic acid (1:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 O4, C2 H5 N O2'
_chemical_formula_sum            'C10 H11 N O6'
_chemical_formula_weight         241.20

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1330(11)
_cell_length_b                   11.3031(13)
_cell_length_c                   23.884(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2195.6(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3030
_cell_measurement_theta_min      1.75
_cell_measurement_theta_max      27.98

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.500
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            7416
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.705
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1942
_reflns_number_gt                1004
_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)+(0.1060P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_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         1942
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1783
_refine_ls_wR_factor_gt          0.1338
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_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
O1 O 0.2512(3) 0.1162(2) 0.48180(10) 0.0602(7) Uani 1 1 d . . . . .
O6 O 0.7020(3) 0.0586(2) 0.58516(12) 0.0715(8) Uani 1 1 d . . . . .
H6A H 0.7094 0.0043 0.5625 0.12(2) Uiso 1 1 calc R . . . .
O3 O 0.4378(3) 0.2303(2) 0.58564(11) 0.0690(8) Uani 1 1 d . . . . .
O2 O 0.1590(3) -0.0201(2) 0.54159(11) 0.0707(8) Uani 1 1 d . . . . .
O4 O 0.4858(5) 0.4012(2) 0.62911(13) 0.0825(9) Uani 1 1 d . . . . .
H4 H 0.4308 0.4276 0.6032 0.14(2) Uiso 1 1 calc R . . . .
O5 O 0.5081(4) -0.0570(2) 0.62201(12) 0.0799(9) Uani 1 1 d . . . . .
C4 C 0.5598(4) 0.2267(3) 0.67647(14) 0.0533(9) Uani 1 1 d . . . . .
C9 C 0.6027(4) 0.1063(3) 0.67534(14) 0.0547(9) Uani 1 1 d . . . . .
C1 C 0.1693(4) 0.0843(3) 0.52373(15) 0.0539(8) Uani 1 1 d . . . . .
C3 C 0.4903(4) 0.2844(3) 0.62584(16) 0.0576(9) Uani 1 1 d . . . . .
C8 C 0.6570(5) 0.0535(4) 0.72473(17) 0.0670(10) Uani 1 1 d . . . . .
H8 H 0.6860 -0.0261 0.7245 0.082(13) Uiso 1 1 calc R . . . .
N1 N 0.0930(4) 0.2961(2) 0.52921(14) 0.0609(8) Uani 1 1 d . . . . .
H1A H 0.0621 0.2929 0.4935 0.115(19) Uiso 1 1 calc R . . . .
H1B H 0.1980 0.3180 0.5312 0.097(16) Uiso 1 1 calc R . . . .
H1C H 0.0309 0.3484 0.5474 0.111(18) Uiso 1 1 calc R . . . .
C2 C 0.0733(4) 0.1789(3) 0.55492(16) 0.0575(9) Uani 1 1 d . . . . .
H2A H -0.0423 0.1578 0.5552 0.079(12) Uiso 1 1 calc R . . . .
H2B H 0.1108 0.1820 0.5934 0.079(13) Uiso 1 1 calc R . . . .
C5 C 0.5713(5) 0.2884(3) 0.72619(16) 0.0632(10) Uani 1 1 d . . . . .
H5 H 0.5421 0.3679 0.7271 0.078(12) Uiso 1 1 calc R . . . .
C10 C 0.5966(5) 0.0295(3) 0.62471(16) 0.0590(9) Uani 1 1 d . . . . .
C7 C 0.6686(5) 0.1167(4) 0.77394(18) 0.0736(11) Uani 1 1 d . . . . .
H7 H 0.7055 0.0799 0.8064 0.082(13) Uiso 1 1 calc R . . . .
C6 C 0.6256(5) 0.2341(4) 0.77489(17) 0.0736(11) Uani 1 1 d . . . . .
H6 H 0.6329 0.2771 0.8080 0.079(12) Uiso 1 1 calc R . . . .


_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
O1 C1 1.255(4) . ?
O6 C10 1.317(4) . ?
O6 H6A 0.8200 . ?
O3 C3 1.216(4) . ?
O2 C1 1.257(4) . ?
O4 C3 1.323(4) . ?
O4 H4 0.8200 . ?
O5 C10 1.216(4) . ?
C4 C5 1.380(5) . ?
C4 C9 1.406(5) . ?
C4 C3 1.485(5) . ?
C9 C8 1.394(5) . ?
C9 C10 1.489(5) . ?
C1 C2 1.519(5) . ?
C8 C7 1.379(6) . ?
C8 H8 0.9300 . ?
N1 C2 1.469(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 C6 1.387(6) . ?
C5 H5 0.9300 . ?
C7 C6 1.372(6) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?

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
C10 O6 H6A 109.5 . . ?
C3 O4 H4 109.5 . . ?
C5 C4 C9 119.3(3) . . ?
C5 C4 C3 120.3(3) . . ?
C9 C4 C3 120.3(3) . . ?
C8 C9 C4 118.5(3) . . ?
C8 C9 C10 116.6(3) . . ?
C4 C9 C10 124.9(3) . . ?
O1 C1 O2 125.1(3) . . ?
O1 C1 C2 117.5(3) . . ?
O2 C1 C2 117.3(3) . . ?
O3 C3 O4 122.6(3) . . ?
O3 C3 C4 123.8(3) . . ?
O4 C3 C4 113.6(3) . . ?
C7 C8 C9 121.4(4) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N1 C2 C1 111.9(3) . . ?
N1 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
O5 C10 O6 123.2(3) . . ?
O5 C10 C9 122.1(3) . . ?
O6 C10 C9 114.5(3) . . ?
C6 C7 C8 119.9(4) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C6 C5 119.7(4) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?

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
C5 C4 C9 C8 -0.5(5) . . . . ?
C3 C4 C9 C8 -175.7(3) . . . . ?
C5 C4 C9 C10 -179.8(3) . . . . ?
C3 C4 C9 C10 5.0(5) . . . . ?
C5 C4 C3 O3 -160.6(4) . . . . ?
C9 C4 C3 O3 14.6(5) . . . . ?
C5 C4 C3 O4 17.4(5) . . . . ?
C9 C4 C3 O4 -167.5(3) . . . . ?
C4 C9 C8 C7 0.1(5) . . . . ?
C10 C9 C8 C7 179.5(4) . . . . ?
O1 C1 C2 N1 0.4(5) . . . . ?
O2 C1 C2 N1 -178.8(3) . . . . ?
C9 C4 C5 C6 0.5(5) . . . . ?
C3 C4 C5 C6 175.7(4) . . . . ?
C8 C9 C10 O5 62.4(5) . . . . ?
C4 C9 C10 O5 -118.3(4) . . . . ?
C8 C9 C10 O6 -113.3(4) . . . . ?
C4 C9 C10 O6 66.0(5) . . . . ?
C9 C8 C7 C6 0.3(6) . . . . ?
C8 C7 C6 C5 -0.3(6) . . . . ?
C4 C5 C6 C7 -0.1(6) . . . . ?

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
O4 H4 O2 0.82 1.75 2.559(4) 171.1 7_665
O6 H6A O1 0.82 1.75 2.570(4) 172.8 5_656
N1 H1A O3 0.89 2.16 3.034(4) 167.4 3_456
N1 H1B O3 0.89 2.54 3.198(4) 130.8 .
N1 H1B O2 0.89 2.18 2.911(4) 138.6 7_665
N1 H1C O5 0.89 2.10 2.889(4) 146.7 7_665

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.225
_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_gph275K
_database_code_depnum_ccdc_archive 'CCDC 1437186'
_audit_update_record             
;
2016-06-01 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-phthalic acid (1:1)'
_chemical_name_common            'glycine-phthalic acid (1:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 O4, C2 H5 N O2'
_chemical_formula_sum            'C10 H11 N O6'
_chemical_formula_weight         241.20

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1071(11)
_cell_length_b                   11.3252(12)
_cell_length_c                   23.827(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2187.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    275(2)
_cell_measurement_reflns_used    3255
_cell_measurement_theta_min      1.74
_cell_measurement_theta_max      28.72

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.995
_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            7330
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.709
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.019
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1936
_reflns_number_gt                1098
_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)+(0.0565P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0101(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1936
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_restrained_S_all      0.923
_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
O1 O 0.2513(2) 0.11588(15) 0.48182(7) 0.0487(5) Uani 1 1 d . . . . .
O6 O 0.7015(2) 0.05864(16) 0.58480(9) 0.0580(5) Uani 1 1 d . . . . .
H6A H 0.7093 0.0043 0.5622 0.096(13) Uiso 1 1 calc R . . . .
O3 O 0.4377(2) 0.23070(15) 0.58542(8) 0.0551(5) Uani 1 1 d . . . . .
O2 O 0.1577(2) -0.01965(15) 0.54150(8) 0.0572(5) Uani 1 1 d . . . . .
O4 O 0.4876(3) 0.40112(16) 0.62913(9) 0.0677(6) Uani 1 1 d . . . . .
H4 H 0.4440 0.4283 0.6009 0.113(16) Uiso 1 1 calc R . . . .
O5 O 0.5068(3) -0.05714(16) 0.62194(9) 0.0658(6) Uani 1 1 d . . . . .
C4 C 0.5608(3) 0.2269(2) 0.67626(10) 0.0417(6) Uani 1 1 d . . . . .
C9 C 0.6028(3) 0.1064(2) 0.67543(10) 0.0428(6) Uani 1 1 d . . . . .
C1 C 0.1686(3) 0.0846(2) 0.52385(11) 0.0422(6) Uani 1 1 d . . . . .
C3 C 0.4906(3) 0.2850(2) 0.62580(12) 0.0451(6) Uani 1 1 d . . . . .
C8 C 0.6563(3) 0.0530(2) 0.72474(12) 0.0536(7) Uani 1 1 d . . . . .
H8 H 0.6845 -0.0267 0.7244 0.069(9) Uiso 1 1 calc R . . . .
N1 N 0.0941(3) 0.29630(17) 0.52951(10) 0.0492(6) Uani 1 1 d . . . . .
H1A H 0.0637 0.2937 0.4936 0.074(10) Uiso 1 1 calc R . . . .
H1B H 0.1995 0.3177 0.5318 0.081(11) Uiso 1 1 calc R . . . .
H1C H 0.0319 0.3486 0.5477 0.091(12) Uiso 1 1 calc R . . . .
C2 C 0.0726(3) 0.1787(2) 0.55503(11) 0.0452(6) Uani 1 1 d . . . . .
H2A H -0.0435 0.1582 0.5549 0.062(8) Uiso 1 1 calc R . . . .
H2B H 0.1094 0.1812 0.5938 0.067(9) Uiso 1 1 calc R . . . .
C5 C 0.5730(3) 0.2885(2) 0.72630(11) 0.0518(7) Uani 1 1 d . . . . .
H5 H 0.5453 0.3682 0.7271 0.075(9) Uiso 1 1 calc R . . . .
C10 C 0.5959(3) 0.0296(2) 0.62431(11) 0.0478(6) Uani 1 1 d . . . . .
C7 C 0.6682(4) 0.1163(3) 0.77428(13) 0.0614(8) Uani 1 1 d . . . . .
H7 H 0.7049 0.0795 0.8069 0.077(10) Uiso 1 1 calc R . . . .
C6 C 0.6254(4) 0.2343(3) 0.77508(12) 0.0601(8) Uani 1 1 d . . . . .
H6 H 0.6319 0.2771 0.8083 0.075(9) Uiso 1 1 calc R . . . .


_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
O1 C1 1.256(3) . ?
O6 C10 1.314(3) . ?
O6 H6A 0.8200 . ?
O3 C3 1.220(3) . ?
O2 C1 1.256(3) . ?
O4 C3 1.318(3) . ?
O4 H4 0.8200 . ?
O5 C10 1.221(3) . ?
C4 C5 1.385(4) . ?
C4 C9 1.407(3) . ?
C4 C3 1.484(4) . ?
C9 C8 1.391(4) . ?
C9 C10 1.498(4) . ?
C1 C2 1.514(3) . ?
C8 C7 1.385(4) . ?
C8 H8 0.9300 . ?
N1 C2 1.475(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C7 C6 1.381(4) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?

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
C10 O6 H6A 109.5 . . ?
C3 O4 H4 109.5 . . ?
C5 C4 C9 118.9(2) . . ?
C5 C4 C3 120.1(2) . . ?
C9 C4 C3 120.8(2) . . ?
C8 C9 C4 119.1(2) . . ?
C8 C9 C10 116.5(2) . . ?
C4 C9 C10 124.4(2) . . ?
O1 C1 O2 124.7(2) . . ?
O1 C1 C2 117.8(2) . . ?
O2 C1 C2 117.5(2) . . ?
O3 C3 O4 123.0(3) . . ?
O3 C3 C4 123.4(2) . . ?
O4 C3 C4 113.6(2) . . ?
C7 C8 C9 121.1(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N1 C2 C1 111.9(2) . . ?
N1 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
O5 C10 O6 123.6(2) . . ?
O5 C10 C9 121.8(2) . . ?
O6 C10 C9 114.4(2) . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C6 C5 119.7(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?

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
C5 C4 C9 C8 -0.4(3) . . . . ?
C3 C4 C9 C8 -175.1(2) . . . . ?
C5 C4 C9 C10 -179.8(2) . . . . ?
C3 C4 C9 C10 5.5(4) . . . . ?
C5 C4 C3 O3 -160.8(2) . . . . ?
C9 C4 C3 O3 13.9(4) . . . . ?
C5 C4 C3 O4 17.9(3) . . . . ?
C9 C4 C3 O4 -167.5(2) . . . . ?
C4 C9 C8 C7 0.1(4) . . . . ?
C10 C9 C8 C7 179.6(3) . . . . ?
O1 C1 C2 N1 -0.1(3) . . . . ?
O2 C1 C2 N1 -179.1(2) . . . . ?
C9 C4 C5 C6 0.0(4) . . . . ?
C3 C4 C5 C6 174.8(2) . . . . ?
C8 C9 C10 O5 61.5(4) . . . . ?
C4 C9 C10 O5 -119.0(3) . . . . ?
C8 C9 C10 O6 -113.6(3) . . . . ?
C4 C9 C10 O6 65.8(3) . . . . ?
C9 C8 C7 C6 0.5(4) . . . . ?
C8 C7 C6 C5 -0.8(4) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?

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
O4 H4 O2 0.82 1.74 2.560(3) 176.8 7_665
O6 H6A O1 0.82 1.75 2.564(2) 172.9 5_656
N1 H1A O3 0.89 2.16 3.033(3) 166.5 3_456
N1 H1B O3 0.89 2.52 3.176(3) 131.4 .
N1 H1B O2 0.89 2.19 2.911(3) 138.0 7_665
N1 H1C O5 0.89 2.09 2.876(3) 146.8 7_665

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_gph250K
_database_code_depnum_ccdc_archive 'CCDC 1437187'
_audit_update_record             
;
2016-06-01 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-phthalic acid (1:1)'
_chemical_name_common            'glycine-phthalic acid (1:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 O4, C2 H5 N O2'
_chemical_formula_sum            'C10 H11 N O6'
_chemical_formula_weight         241.20

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0808(11)
_cell_length_b                   11.3449(12)
_cell_length_c                   23.766(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2178.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    3531
_cell_measurement_theta_min      1.74
_cell_measurement_theta_max      29.00

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.995
_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            7306
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.714
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_full        25.017
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1930
_reflns_number_gt                1110
_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)+(0.0621P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0114(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1930
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_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
O1 O 0.2513(2) 0.11601(16) 0.48167(8) 0.0455(5) Uani 1 1 d . . . . .
O6 O 0.7007(2) 0.05885(16) 0.58446(9) 0.0533(5) Uani 1 1 d . . . . .
H6A H 0.7078 0.0040 0.5614 0.081(12) Uiso 1 1 calc R . . . .
O3 O 0.4371(2) 0.23129(16) 0.58523(8) 0.0507(5) Uani 1 1 d . . . . .
O2 O 0.1568(2) -0.01975(16) 0.54156(8) 0.0531(6) Uani 1 1 d . . . . .
O4 O 0.4900(3) 0.40106(16) 0.62911(9) 0.0624(6) Uani 1 1 d . . . . .
H4 H 0.4455 0.4289 0.6006 0.093(14) Uiso 1 1 calc R . . . .
O5 O 0.5059(3) -0.05713(17) 0.62206(9) 0.0607(6) Uani 1 1 d . . . . .
C4 C 0.5610(3) 0.2268(2) 0.67618(10) 0.0396(6) Uani 1 1 d . . . . .
C9 C 0.6019(3) 0.1063(2) 0.67540(11) 0.0399(6) Uani 1 1 d . . . . .
C1 C 0.1681(3) 0.0844(2) 0.52383(11) 0.0405(6) Uani 1 1 d . . . . .
C3 C 0.4915(3) 0.2854(2) 0.62567(12) 0.0423(6) Uani 1 1 d . . . . .
C8 C 0.6559(3) 0.0529(3) 0.72492(12) 0.0502(7) Uani 1 1 d . . . . .
H8 H 0.6843 -0.0275 0.7246 0.059(9) Uiso 1 1 calc R . . . .
N1 N 0.0952(3) 0.29654(18) 0.52981(10) 0.0458(6) Uani 1 1 d . . . . .
H1A H 0.0620 0.2951 0.4937 0.074(11) Uiso 1 1 calc R . . . .
H1B H 0.2028 0.3166 0.5314 0.072(10) Uiso 1 1 calc R . . . .
H1C H 0.0347 0.3497 0.5490 0.083(12) Uiso 1 1 calc R . . . .
C2 C 0.0722(3) 0.1785(2) 0.55507(12) 0.0434(7) Uani 1 1 d . . . . .
H2A H -0.0458 0.1583 0.5547 0.061(9) Uiso 1 1 calc R . . . .
H2B H 0.1087 0.1804 0.5944 0.064(9) Uiso 1 1 calc R . . . .
C5 C 0.5742(3) 0.2886(2) 0.72651(12) 0.0480(7) Uani 1 1 d . . . . .
H5 H 0.5469 0.3691 0.7273 0.074(10) Uiso 1 1 calc R . . . .
C10 C 0.5949(3) 0.0301(2) 0.62425(12) 0.0443(6) Uani 1 1 d . . . . .
C7 C 0.6683(4) 0.1160(3) 0.77458(13) 0.0571(8) Uani 1 1 d . . . . .
H7 H 0.7050 0.0786 0.8076 0.070(10) Uiso 1 1 calc R . . . .
C6 C 0.6267(4) 0.2340(3) 0.77542(13) 0.0553(8) Uani 1 1 d . . . . .
H6 H 0.6341 0.2772 0.8091 0.069(10) Uiso 1 1 calc R . . . .


_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
O1 C1 1.259(3) . ?
O6 C10 1.316(3) . ?
O6 H6A 0.8300 . ?
O3 C3 1.222(3) . ?
O2 C1 1.258(3) . ?
O4 C3 1.314(3) . ?
O4 H4 0.8300 . ?
O5 C10 1.225(3) . ?
C4 C5 1.390(4) . ?
C4 C9 1.407(4) . ?
C4 C3 1.483(4) . ?
C9 C8 1.394(4) . ?
C9 C10 1.493(4) . ?
C1 C2 1.513(4) . ?
C8 C7 1.384(4) . ?
C8 H8 0.9400 . ?
N1 C2 1.480(3) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N1 H1C 0.9000 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9400 . ?
C7 C6 1.381(4) . ?
C7 H7 0.9400 . ?
C6 H6 0.9400 . ?

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
C10 O6 H6A 109.5 . . ?
C3 O4 H4 109.5 . . ?
C5 C4 C9 118.9(2) . . ?
C5 C4 C3 120.0(2) . . ?
C9 C4 C3 120.9(2) . . ?
C8 C9 C4 119.0(2) . . ?
C8 C9 C10 116.6(2) . . ?
C4 C9 C10 124.4(2) . . ?
O2 C1 O1 125.0(2) . . ?
O2 C1 C2 117.4(2) . . ?
O1 C1 C2 117.6(2) . . ?
O3 C3 O4 123.2(3) . . ?
O3 C3 C4 123.2(2) . . ?
O4 C3 C4 113.6(2) . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N1 C2 C1 112.0(2) . . ?
N1 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
O5 C10 O6 123.5(3) . . ?
O5 C10 C9 121.6(2) . . ?
O6 C10 C9 114.7(2) . . ?
C6 C7 C8 119.8(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?

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
C5 C4 C9 C8 -0.7(4) . . . . ?
C3 C4 C9 C8 -175.5(2) . . . . ?
C5 C4 C9 C10 -179.3(2) . . . . ?
C3 C4 C9 C10 5.8(4) . . . . ?
C5 C4 C3 O3 -160.6(3) . . . . ?
C9 C4 C3 O3 14.2(4) . . . . ?
C5 C4 C3 O4 17.8(4) . . . . ?
C9 C4 C3 O4 -167.4(2) . . . . ?
C4 C9 C8 C7 0.6(4) . . . . ?
C10 C9 C8 C7 179.4(3) . . . . ?
O2 C1 C2 N1 -179.6(2) . . . . ?
O1 C1 C2 N1 -0.6(3) . . . . ?
C9 C4 C5 C6 0.2(4) . . . . ?
C3 C4 C5 C6 175.1(3) . . . . ?
C8 C9 C10 O5 61.2(4) . . . . ?
C4 C9 C10 O5 -120.1(3) . . . . ?
C8 C9 C10 O6 -113.5(3) . . . . ?
C4 C9 C10 O6 65.2(3) . . . . ?
C9 C8 C7 C6 0.0(4) . . . . ?
C8 C7 C6 C5 -0.5(4) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?

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
O4 H4 O2 0.83 1.73 2.558(3) 176.4 7_665
O6 H6A O1 0.83 1.74 2.560(3) 171.8 5_656
N1 H1A O3 0.90 2.15 3.034(3) 167.1 3_456
N1 H1B O3 0.90 2.48 3.149(3) 131.4 .
N1 H1B O2 0.90 2.19 2.905(3) 136.1 7_665
N1 H1C O5 0.90 2.06 2.869(3) 149.0 7_665

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_gph225K
_database_code_depnum_ccdc_archive 'CCDC 1437188'
_audit_update_record             
;
2016-06-01 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-phthalic acid (1:1)'
_chemical_name_common            'glycine-phthalic acid (1:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 O4, C2 H5 N O2'
_chemical_formula_sum            'C10 H11 N O6'
_chemical_formula_weight         241.20

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0565(10)
_cell_length_b                   11.3647(12)
_cell_length_c                   23.719(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2171.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    225(2)
_cell_measurement_reflns_used    3803
_cell_measurement_theta_min      1.69
_cell_measurement_theta_max      29.41

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.995
_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            7299
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.717
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.025
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1926
_reflns_number_gt                1154
_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)+(0.0865P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1926
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1474
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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
O1 O 0.2515(2) 0.11586(18) 0.48174(9) 0.0440(5) Uani 1 1 d . . . . .
O6 O 0.7000(3) 0.05888(18) 0.58408(10) 0.0499(6) Uani 1 1 d . . . . .
H6A H 0.7079 0.0037 0.5613 0.081(14) Uiso 1 1 calc R . . . .
O3 O 0.4367(2) 0.23185(18) 0.58524(9) 0.0478(6) Uani 1 1 d . . . . .
O2 O 0.1558(3) -0.01954(18) 0.54154(9) 0.0508(6) Uani 1 1 d . . . . .
O4 O 0.4921(4) 0.40178(19) 0.62891(10) 0.0583(7) Uani 1 1 d . . . . .
H4 H 0.4440 0.4296 0.6010 0.12(2) Uiso 1 1 calc R . . . .
O5 O 0.5052(3) -0.0569(2) 0.62211(10) 0.0579(7) Uani 1 1 d . . . . .
C4 C 0.5616(3) 0.2263(2) 0.67641(11) 0.0375(7) Uani 1 1 d . . . . .
C9 C 0.6024(3) 0.1063(3) 0.67549(12) 0.0393(7) Uani 1 1 d . . . . .
C1 C 0.1675(3) 0.0848(3) 0.52404(13) 0.0390(7) Uani 1 1 d . . . . .
C3 C 0.4923(4) 0.2855(3) 0.62559(13) 0.0409(7) Uani 1 1 d . . . . .
C8 C 0.6551(4) 0.0527(3) 0.72495(14) 0.0488(8) Uani 1 1 d . . . . .
H8 H 0.6824 -0.0277 0.7247 0.080(13) Uiso 1 1 calc R . . . .
N1 N 0.0962(3) 0.2964(2) 0.53014(11) 0.0433(6) Uani 1 1 d . . . . .
H1A H 0.0629 0.2953 0.4939 0.076(13) Uiso 1 1 calc R . . . .
H1B H 0.2043 0.3160 0.5318 0.060(10) Uiso 1 1 calc R . . . .
H1C H 0.0360 0.3497 0.5494 0.078(13) Uiso 1 1 calc R . . . .
C2 C 0.0722(4) 0.1791(2) 0.55522(13) 0.0411(7) Uani 1 1 d . . . . .
H2A H -0.0462 0.1595 0.5547 0.060(10) Uiso 1 1 calc R . . . .
H2B H 0.1087 0.1808 0.5946 0.049(9) Uiso 1 1 calc R . . . .
C5 C 0.5752(4) 0.2883(3) 0.72660(13) 0.0460(7) Uani 1 1 d . . . . .
H5 H 0.5482 0.3688 0.7272 0.070(11) Uiso 1 1 calc R . . . .
C10 C 0.5949(4) 0.0304(3) 0.62401(13) 0.0437(7) Uani 1 1 d . . . . .
C7 C 0.6681(4) 0.1158(3) 0.77465(14) 0.0537(8) Uani 1 1 d . . . . .
H7 H 0.7044 0.0780 0.8077 0.064(11) Uiso 1 1 calc R . . . .
C6 C 0.6279(4) 0.2340(3) 0.77597(14) 0.0521(8) Uani 1 1 d . . . . .
H6 H 0.6360 0.2769 0.8097 0.067(11) Uiso 1 1 calc R . . . .


_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
O1 C1 1.261(3) . ?
O6 C10 1.311(4) . ?
O6 H6A 0.8300 . ?
O3 C3 1.220(3) . ?
O2 C1 1.260(4) . ?
O4 C3 1.323(4) . ?
O4 H4 0.8300 . ?
O5 C10 1.228(4) . ?
C4 C5 1.388(4) . ?
C4 C9 1.404(4) . ?
C4 C3 1.489(4) . ?
C9 C8 1.388(4) . ?
C9 C10 1.496(4) . ?
C1 C2 1.511(4) . ?
C8 C7 1.383(5) . ?
C8 H8 0.9400 . ?
N1 C2 1.473(4) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N1 H1C 0.9000 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C5 C6 1.390(5) . ?
C5 H5 0.9400 . ?
C7 C6 1.382(5) . ?
C7 H7 0.9400 . ?
C6 H6 0.9400 . ?

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
C10 O6 H6A 109.5 . . ?
C3 O4 H4 109.5 . . ?
C5 C4 C9 119.2(3) . . ?
C5 C4 C3 119.6(3) . . ?
C9 C4 C3 121.0(2) . . ?
C8 C9 C4 119.0(3) . . ?
C8 C9 C10 116.7(3) . . ?
C4 C9 C10 124.3(3) . . ?
O2 C1 O1 124.5(3) . . ?
O2 C1 C2 117.9(3) . . ?
O1 C1 C2 117.6(3) . . ?
O3 C3 O4 123.1(3) . . ?
O3 C3 C4 123.1(3) . . ?
O4 C3 C4 113.8(3) . . ?
C7 C8 C9 121.1(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N1 C2 C1 112.2(2) . . ?
N1 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
O5 C10 O6 123.6(3) . . ?
O5 C10 C9 121.3(3) . . ?
O6 C10 C9 114.9(3) . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C6 C5 119.0(3) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?

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
C5 C4 C9 C8 0.1(4) . . . . ?
C3 C4 C9 C8 -175.3(3) . . . . ?
C5 C4 C9 C10 -179.2(3) . . . . ?
C3 C4 C9 C10 5.4(4) . . . . ?
C5 C4 C3 O3 -160.4(3) . . . . ?
C9 C4 C3 O3 15.0(4) . . . . ?
C5 C4 C3 O4 17.8(4) . . . . ?
C9 C4 C3 O4 -166.8(3) . . . . ?
C4 C9 C8 C7 -0.1(4) . . . . ?
C10 C9 C8 C7 179.2(3) . . . . ?
O2 C1 C2 N1 -179.6(3) . . . . ?
O1 C1 C2 N1 -0.6(4) . . . . ?
C9 C4 C5 C6 -0.2(4) . . . . ?
C3 C4 C5 C6 175.3(3) . . . . ?
C8 C9 C10 O5 60.4(4) . . . . ?
C4 C9 C10 O5 -120.2(3) . . . . ?
C8 C9 C10 O6 -114.2(3) . . . . ?
C4 C9 C10 O6 65.1(4) . . . . ?
C9 C8 C7 C6 0.3(5) . . . . ?
C8 C7 C6 C5 -0.3(5) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?

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
O4 H4 O2 0.83 1.72 2.552(3) 177.1 7_665
O6 H6A O1 0.83 1.73 2.556(3) 172.5 5_656
N1 H1A O3 0.90 2.16 3.040(3) 166.7 3_456
N1 H1B O3 0.90 2.46 3.126(3) 131.6 .
N1 H1B O2 0.90 2.19 2.905(3) 135.4 7_665
N1 H1C O5 0.90 2.05 2.864(3) 149.5 7_665

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.243
_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_gph200K
_database_code_depnum_ccdc_archive 'CCDC 1437189'
_audit_update_record             
;
2016-06-01 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-phthalic acid (1:1)'
_chemical_name_common            'glycine-phthalic acid (1:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 O4, C2 H5 N O2'
_chemical_formula_sum            'C10 H11 N O6'
_chemical_formula_weight         241.20

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0324(10)
_cell_length_b                   11.3875(11)
_cell_length_c                   23.665(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2164.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4002
_cell_measurement_theta_min      1.68
_cell_measurement_theta_max      29.39

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.995
_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            7275
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.721
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1921
_reflns_number_gt                1188
_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)+(0.0952P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_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         1921
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1581
_refine_ls_wR_factor_gt          0.1240
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
O1 O 0.2519(2) 0.11599(18) 0.48167(9) 0.0404(6) Uani 1 1 d . . . . .
O6 O 0.6987(3) 0.05944(18) 0.58362(10) 0.0454(6) Uani 1 1 d . . . . .
H6A H 0.7068 0.0038 0.5605 0.051(10) Uiso 1 1 calc R . . . .
O3 O 0.4364(3) 0.23258(19) 0.58494(9) 0.0442(6) Uani 1 1 d . . . . .
O2 O 0.1548(3) -0.01874(19) 0.54151(9) 0.0462(6) Uani 1 1 d . . . . .
O4 O 0.4938(4) 0.40201(19) 0.62890(10) 0.0533(7) Uani 1 1 d . . . . .
H4 H 0.4467 0.4304 0.6003 0.12(2) Uiso 1 1 calc R . . . .
O5 O 0.5040(3) -0.0571(2) 0.62210(10) 0.0518(7) Uani 1 1 d . . . . .
C4 C 0.5629(3) 0.2272(3) 0.67631(12) 0.0371(7) Uani 1 1 d . . . . .
C9 C 0.6017(3) 0.1062(3) 0.67552(12) 0.0361(7) Uani 1 1 d . . . . .
C1 C 0.1672(3) 0.0851(3) 0.52394(13) 0.0359(7) Uani 1 1 d . . . . .
C3 C 0.4932(4) 0.2863(3) 0.62545(13) 0.0378(7) Uani 1 1 d . . . . .
C8 C 0.6542(4) 0.0525(3) 0.72510(14) 0.0452(8) Uani 1 1 d . . . . .
H8 H 0.6810 -0.0287 0.7248 0.075(13) Uiso 1 1 calc R . . . .
N1 N 0.0971(3) 0.2964(2) 0.53052(11) 0.0404(6) Uani 1 1 d . . . . .
H1A H 0.0619 0.2962 0.4940 0.057(11) Uiso 1 1 calc R . . . .
H1B H 0.2072 0.3149 0.5318 0.061(11) Uiso 1 1 calc R . . . .
H1C H 0.0380 0.3505 0.5505 0.070(12) Uiso 1 1 calc R . . . .
C2 C 0.0713(4) 0.1788(2) 0.55539(13) 0.0383(7) Uani 1 1 d . . . . .
H2A H -0.0488 0.1594 0.5545 0.048(9) Uiso 1 1 calc R . . . .
H2B H 0.1074 0.1798 0.5954 0.062(11) Uiso 1 1 calc R . . . .
C5 C 0.5762(4) 0.2884(3) 0.72691(13) 0.0432(8) Uani 1 1 d . . . . .
H5 H 0.5487 0.3695 0.7277 0.071(12) Uiso 1 1 calc R . . . .
C10 C 0.5940(4) 0.0305(3) 0.62388(13) 0.0407(7) Uani 1 1 d . . . . .
C7 C 0.6684(4) 0.1153(3) 0.77500(15) 0.0502(9) Uani 1 1 d . . . . .
H7 H 0.7053 0.0771 0.8084 0.059(10) Uiso 1 1 calc R . . . .
C6 C 0.6289(4) 0.2339(3) 0.77630(14) 0.0475(8) Uani 1 1 d . . . . .
H6 H 0.6378 0.2772 0.8105 0.068(11) Uiso 1 1 calc R . . . .


_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
O1 C1 1.260(4) . ?
O6 C10 1.313(4) . ?
O6 H6A 0.8400 . ?
O3 C3 1.225(4) . ?
O2 C1 1.257(4) . ?
O4 C3 1.320(4) . ?
O4 H4 0.8400 . ?
O5 C10 1.232(4) . ?
C4 C5 1.389(4) . ?
C4 C9 1.413(4) . ?
C4 C3 1.488(4) . ?
C9 C8 1.389(4) . ?
C9 C10 1.497(4) . ?
C1 C2 1.512(4) . ?
C8 C7 1.385(5) . ?
C8 H8 0.9500 . ?
N1 C2 1.478(4) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 C6 1.390(5) . ?
C5 H5 0.9500 . ?
C7 C6 1.387(5) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?

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
C10 O6 H6A 109.5 . . ?
C3 O4 H4 109.5 . . ?
C5 C4 C9 118.9(3) . . ?
C5 C4 C3 120.0(3) . . ?
C9 C4 C3 120.9(3) . . ?
C8 C9 C4 119.0(3) . . ?
C8 C9 C10 116.7(3) . . ?
C4 C9 C10 124.3(3) . . ?
O2 C1 O1 124.6(3) . . ?
O2 C1 C2 117.4(3) . . ?
O1 C1 C2 117.9(3) . . ?
O3 C3 O4 123.2(3) . . ?
O3 C3 C4 123.2(3) . . ?
O4 C3 C4 113.6(3) . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N1 C2 C1 111.9(2) . . ?
N1 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
O5 C10 O6 123.7(3) . . ?
O5 C10 C9 121.2(3) . . ?
O6 C10 C9 114.9(3) . . ?
C8 C7 C6 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C6 C5 119.1(3) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?

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
C5 C4 C9 C8 -0.9(4) . . . . ?
C3 C4 C9 C8 -175.1(3) . . . . ?
C5 C4 C9 C10 -179.4(3) . . . . ?
C3 C4 C9 C10 6.4(4) . . . . ?
C5 C4 C3 O3 -159.7(3) . . . . ?
C9 C4 C3 O3 14.4(4) . . . . ?
C5 C4 C3 O4 18.3(4) . . . . ?
C9 C4 C3 O4 -167.5(3) . . . . ?
C4 C9 C8 C7 0.3(4) . . . . ?
C10 C9 C8 C7 178.9(3) . . . . ?
O2 C1 C2 N1 179.9(3) . . . . ?
O1 C1 C2 N1 -1.0(4) . . . . ?
C9 C4 C5 C6 0.9(4) . . . . ?
C3 C4 C5 C6 175.1(3) . . . . ?
C8 C9 C10 O5 60.1(4) . . . . ?
C4 C9 C10 O5 -121.4(3) . . . . ?
C8 C9 C10 O6 -114.8(3) . . . . ?
C4 C9 C10 O6 63.7(4) . . . . ?
C9 C8 C7 C6 0.4(5) . . . . ?
C8 C7 C6 C5 -0.4(5) . . . . ?
C4 C5 C6 C7 -0.3(5) . . . . ?

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
O4 H4 O2 0.84 1.71 2.553(3) 176.9 7_665
O6 H6A O1 0.84 1.72 2.556(3) 171.9 5_656
N1 H1A O3 0.91 2.15 3.040(3) 166.6 3_456
N1 H1B O3 0.91 2.42 3.101(3) 131.8 .
N1 H1B O2 0.91 2.21 2.911(3) 133.7 7_665
N1 H1C O5 0.91 2.02 2.853(3) 151.0 7_665

_refine_diff_density_max         0.302
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_gph175K
_database_code_depnum_ccdc_archive 'CCDC 1437190'
_audit_update_record             
;
2016-06-01 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-phthalic acid (1:1)'
_chemical_name_common            'glycine-phthalic acid (1:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 O4, C2 H5 N O2'
_chemical_formula_sum            'C10 H11 N O6'
_chemical_formula_weight         241.20

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0056(9)
_cell_length_b                   11.4027(11)
_cell_length_c                   23.615(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2155.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    175(2)
_cell_measurement_reflns_used    4082
_cell_measurement_theta_min      1.77
_cell_measurement_theta_max      29.41

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.995
_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            7200
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.725
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_full        25.023
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1906
_reflns_number_gt                1201
_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)+(0.1123P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1906
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1477
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
O1 O 0.2518(3) 0.1160(2) 0.48160(9) 0.0407(6) Uani 1 1 d . . . . .
O6 O 0.6979(3) 0.0592(2) 0.58311(10) 0.0439(6) Uani 1 1 d . . . . .
H6A H 0.7094 0.0022 0.5609 0.072(14) Uiso 1 1 calc R . . . .
O3 O 0.4361(3) 0.2330(2) 0.58479(10) 0.0431(6) Uani 1 1 d . . . . .
O2 O 0.1539(3) -0.0190(2) 0.54168(10) 0.0450(6) Uani 1 1 d . . . . .
O4 O 0.4957(4) 0.4021(2) 0.62874(11) 0.0507(7) Uani 1 1 d . . . . .
H4 H 0.4446 0.4305 0.6009 0.14(3) Uiso 1 1 calc R . . . .
O5 O 0.5032(3) -0.0570(2) 0.62216(10) 0.0504(7) Uani 1 1 d . . . . .
C4 C 0.5634(3) 0.2270(3) 0.67624(13) 0.0361(7) Uani 1 1 d . . . . .
C9 C 0.6017(4) 0.1066(3) 0.67554(13) 0.0370(7) Uani 1 1 d . . . . .
C1 C 0.1667(4) 0.0857(3) 0.52408(13) 0.0359(7) Uani 1 1 d . . . . .
C3 C 0.4942(4) 0.2867(3) 0.62537(14) 0.0380(7) Uani 1 1 d . . . . .
C8 C 0.6537(4) 0.0525(3) 0.72516(14) 0.0439(8) Uani 1 1 d . . . . .
H8 H 0.6799 -0.0288 0.7247 0.076(14) Uiso 1 1 calc R . . . .
N1 N 0.0978(3) 0.2962(2) 0.53075(12) 0.0399(7) Uani 1 1 d . . . . .
H1A H 0.0608 0.2968 0.4943 0.061(12) Uiso 1 1 calc R . . . .
H1B H 0.2087 0.3136 0.5315 0.057(11) Uiso 1 1 calc R . . . .
H1C H 0.0405 0.3506 0.5512 0.075(14) Uiso 1 1 calc R . . . .
C2 C 0.0707(4) 0.1789(3) 0.55550(14) 0.0387(8) Uani 1 1 d . . . . .
H2A H -0.0499 0.1599 0.5544 0.055(11) Uiso 1 1 calc R . . . .
H2B H 0.1063 0.1795 0.5956 0.056(11) Uiso 1 1 calc R . . . .
C5 C 0.5770(4) 0.2884(3) 0.72708(14) 0.0430(8) Uani 1 1 d . . . . .
H5 H 0.5495 0.3694 0.7280 0.066(12) Uiso 1 1 calc R . . . .
C10 C 0.5934(4) 0.0305(3) 0.62374(14) 0.0406(8) Uani 1 1 d . . . . .
C7 C 0.6682(4) 0.1147(3) 0.77521(15) 0.0468(9) Uani 1 1 d . . . . .
H7 H 0.7042 0.0763 0.8088 0.059(11) Uiso 1 1 calc R . . . .
C6 C 0.6299(4) 0.2336(3) 0.77631(15) 0.0466(9) Uani 1 1 d . . . . .
H6 H 0.6399 0.2769 0.8105 0.063(11) Uiso 1 1 calc R . . . .


_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
O1 C1 1.261(4) . ?
O6 C10 1.314(4) . ?
O6 H6A 0.8400 . ?
O3 C3 1.229(4) . ?
O2 C1 1.268(4) . ?
O4 C3 1.317(4) . ?
O4 H4 0.8400 . ?
O5 C10 1.233(4) . ?
C4 C5 1.394(5) . ?
C4 C9 1.407(5) . ?
C4 C3 1.488(5) . ?
C9 C8 1.388(5) . ?
C9 C10 1.501(5) . ?
C1 C2 1.507(4) . ?
C8 C7 1.384(5) . ?
C8 H8 0.9500 . ?
N1 C2 1.476(4) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 C6 1.386(5) . ?
C5 H5 0.9500 . ?
C7 C6 1.390(5) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?

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
C10 O6 H6A 109.5 . . ?
C3 O4 H4 109.5 . . ?
C5 C4 C9 118.9(3) . . ?
C5 C4 C3 119.6(3) . . ?
C9 C4 C3 121.2(3) . . ?
C8 C9 C4 119.3(3) . . ?
C8 C9 C10 116.4(3) . . ?
C4 C9 C10 124.3(3) . . ?
O1 C1 O2 124.2(3) . . ?
O1 C1 C2 118.3(3) . . ?
O2 C1 C2 117.5(3) . . ?
O3 C3 O4 123.3(3) . . ?
O3 C3 C4 122.8(3) . . ?
O4 C3 C4 113.9(3) . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N1 C2 C1 111.7(3) . . ?
N1 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
O5 C10 O6 123.5(3) . . ?
O5 C10 C9 121.2(3) . . ?
O6 C10 C9 115.1(3) . . ?
C8 C7 C6 119.9(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C5 C6 C7 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?

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
C5 C4 C9 C8 -0.8(4) . . . . ?
C3 C4 C9 C8 -175.0(3) . . . . ?
C5 C4 C9 C10 -179.6(3) . . . . ?
C3 C4 C9 C10 6.2(4) . . . . ?
C5 C4 C3 O3 -159.4(3) . . . . ?
C9 C4 C3 O3 14.8(4) . . . . ?
C5 C4 C3 O4 18.5(4) . . . . ?
C9 C4 C3 O4 -167.3(3) . . . . ?
C4 C9 C8 C7 0.2(5) . . . . ?
C10 C9 C8 C7 179.1(3) . . . . ?
O1 C1 C2 N1 -1.5(4) . . . . ?
O2 C1 C2 N1 179.7(3) . . . . ?
C9 C4 C5 C6 1.1(5) . . . . ?
C3 C4 C5 C6 175.4(3) . . . . ?
C8 C9 C10 O5 59.5(4) . . . . ?
C4 C9 C10 O5 -121.7(4) . . . . ?
C8 C9 C10 O6 -115.4(3) . . . . ?
C4 C9 C10 O6 63.5(4) . . . . ?
C9 C8 C7 C6 0.1(5) . . . . ?
C4 C5 C6 C7 -0.8(5) . . . . ?
C8 C7 C6 C5 0.2(5) . . . . ?

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
O4 H4 O2 0.84 1.71 2.544(3) 176.3 7_665
O6 H6A O1 0.84 1.71 2.547(3) 175.3 5_656
N1 H1A O3 0.91 2.14 3.038(4) 166.8 3_456
N1 H1B O3 0.91 2.40 3.080(3) 131.9 .
N1 H1B O2 0.91 2.22 2.909(3) 132.4 7_665
N1 H1C O5 0.91 2.01 2.848(4) 152.6 7_665

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_gph150K
_database_code_depnum_ccdc_archive 'CCDC 1437191'
_audit_update_record             
;
2016-06-01 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-phthalic acid (1:1)'
_chemical_name_common            'glycine-phthalic acid (1:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 O4, C2 H5 N O2'
_chemical_formula_sum            'C10 H11 N O6'
_chemical_formula_weight         241.20

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.9837(10)
_cell_length_b                   11.4209(12)
_cell_length_c                   23.589(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2150.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3967
_cell_measurement_theta_min      1.77
_cell_measurement_theta_max      29.39

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.995
_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            7144
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.727
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_full        25.022
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1900
_reflns_number_gt                1203
_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)+(0.0710P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0118(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1900
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_restrained_S_all      0.927
_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
O1 O 0.2522(2) 0.11602(15) 0.48165(7) 0.0328(4) Uani 1 1 d . . . . .
O6 O 0.6970(2) 0.05960(15) 0.58273(8) 0.0360(5) Uani 1 1 d . . . . .
H6A H 0.7051 0.0039 0.5596 0.063(11) Uiso 1 1 calc R . . . .
O3 O 0.4361(2) 0.23337(15) 0.58462(8) 0.0343(5) Uani 1 1 d . . . . .
O2 O 0.1532(2) -0.01862(15) 0.54162(8) 0.0370(5) Uani 1 1 d . . . . .
O4 O 0.4979(3) 0.40214(15) 0.62883(8) 0.0417(5) Uani 1 1 d . . . . .
H4 H 0.4449 0.4309 0.6014 0.090(15) Uiso 1 1 calc R . . . .
O5 O 0.5024(2) -0.05694(16) 0.62230(8) 0.0415(5) Uani 1 1 d . . . . .
C4 C 0.5641(3) 0.2270(2) 0.67610(10) 0.0293(6) Uani 1 1 d . . . . .
C9 C 0.6014(3) 0.1062(2) 0.67546(10) 0.0290(6) Uani 1 1 d . . . . .
C1 C 0.1663(3) 0.0851(2) 0.52397(11) 0.0300(6) Uani 1 1 d . . . . .
C3 C 0.4954(3) 0.2863(2) 0.62528(11) 0.0313(6) Uani 1 1 d . . . . .
C8 C 0.6535(3) 0.0524(2) 0.72527(12) 0.0358(6) Uani 1 1 d . . . . .
H8 H 0.6794 -0.0288 0.7248 0.060(10) Uiso 1 1 calc R . . . .
N1 N 0.0983(3) 0.29663(17) 0.53095(9) 0.0325(5) Uani 1 1 d . . . . .
H1A H 0.0632 0.2972 0.4943 0.064(10) Uiso 1 1 calc R . . . .
H1B H 0.2094 0.3142 0.5324 0.049(9) Uiso 1 1 calc R . . . .
H1C H 0.0396 0.3508 0.5511 0.058(10) Uiso 1 1 calc R . . . .
C2 C 0.0701(3) 0.1788(2) 0.55566(11) 0.0301(6) Uani 1 1 d . . . . .
H2A H -0.0510 0.1603 0.5544 0.026(6) Uiso 1 1 calc R . . . .
H2B H 0.1056 0.1791 0.5959 0.044(8) Uiso 1 1 calc R . . . .
C5 C 0.5786(3) 0.2879(2) 0.72703(11) 0.0349(6) Uani 1 1 d . . . . .
H5 H 0.5523 0.3690 0.7279 0.060(10) Uiso 1 1 calc R . . . .
C10 C 0.5927(3) 0.0305(2) 0.62371(11) 0.0324(6) Uani 1 1 d . . . . .
C7 C 0.6685(3) 0.1142(3) 0.77560(12) 0.0390(7) Uani 1 1 d . . . . .
H7 H 0.7046 0.0757 0.8092 0.050(9) Uiso 1 1 calc R . . . .
C6 C 0.6304(3) 0.2333(2) 0.77658(12) 0.0378(6) Uani 1 1 d . . . . .
H6 H 0.6398 0.2766 0.8108 0.052(9) Uiso 1 1 calc R . . . .


_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
O1 C1 1.262(3) . ?
O6 C10 1.319(3) . ?
O6 H6A 0.8400 . ?
O3 C3 1.229(3) . ?
O2 C1 1.260(3) . ?
O4 C3 1.325(3) . ?
O4 H4 0.8400 . ?
O5 C10 1.232(3) . ?
C4 C5 1.393(4) . ?
C4 C9 1.412(4) . ?
C4 C3 1.482(4) . ?
C9 C8 1.390(4) . ?
C9 C10 1.497(4) . ?
C1 C2 1.515(3) . ?
C8 C7 1.387(4) . ?
C8 H8 0.9500 . ?
N1 C2 1.483(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C7 C6 1.394(4) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?

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
C10 O6 H6A 109.5 . . ?
C3 O4 H4 109.5 . . ?
C5 C4 C9 118.6(2) . . ?
C5 C4 C3 120.0(2) . . ?
C9 C4 C3 121.1(2) . . ?
C8 C9 C4 119.1(2) . . ?
C8 C9 C10 116.6(2) . . ?
C4 C9 C10 124.3(2) . . ?
O2 C1 O1 124.7(2) . . ?
O2 C1 C2 117.3(2) . . ?
O1 C1 C2 117.9(2) . . ?
O3 C3 O4 123.1(2) . . ?
O3 C3 C4 123.3(2) . . ?
O4 C3 C4 113.5(2) . . ?
C7 C8 C9 121.6(2) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N1 C2 C1 111.7(2) . . ?
N1 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
O5 C10 O6 123.6(2) . . ?
O5 C10 C9 121.2(2) . . ?
O6 C10 C9 115.0(2) . . ?
C8 C7 C6 119.5(3) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C5 C6 C7 119.3(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?

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
C5 C4 C9 C8 -0.9(3) . . . . ?
C3 C4 C9 C8 -175.1(2) . . . . ?
C5 C4 C9 C10 -179.4(2) . . . . ?
C3 C4 C9 C10 6.3(4) . . . . ?
C5 C4 C3 O3 -159.2(2) . . . . ?
C9 C4 C3 O3 15.0(4) . . . . ?
C5 C4 C3 O4 18.3(3) . . . . ?
C9 C4 C3 O4 -167.5(2) . . . . ?
C4 C9 C8 C7 0.4(4) . . . . ?
C10 C9 C8 C7 179.1(2) . . . . ?
O2 C1 C2 N1 179.3(2) . . . . ?
O1 C1 C2 N1 -1.4(3) . . . . ?
C9 C4 C5 C6 0.8(4) . . . . ?
C3 C4 C5 C6 175.1(2) . . . . ?
C8 C9 C10 O5 59.2(3) . . . . ?
C4 C9 C10 O5 -122.3(3) . . . . ?
C8 C9 C10 O6 -115.8(2) . . . . ?
C4 C9 C10 O6 62.7(3) . . . . ?
C9 C8 C7 C6 0.1(4) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C8 C7 C6 C5 -0.2(4) . . . . ?

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
O4 H4 O2 0.84 1.71 2.551(3) 174.9 7_665
O6 H6A O1 0.84 1.71 2.548(2) 171.2 5_656
N1 H1A O3 0.91 2.15 3.037(3) 165.6 3_456
N1 H1B O3 0.91 2.38 3.066(3) 132.5 .
N1 H1B O2 0.91 2.21 2.907(3) 132.6 7_665
N1 H1C O5 0.91 2.01 2.844(3) 151.4 7_665

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_gph125K
_database_code_depnum_ccdc_archive 'CCDC 1437192'
_audit_update_record             
;
2016-06-01 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-phthalic acid (1:1)'
_chemical_name_common            'glycine-phthalic acid (1:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 O4, C2 H5 N O2'
_chemical_formula_sum            'C10 H11 N O6'
_chemical_formula_weight         241.20

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.9621(10)
_cell_length_b                   11.4304(13)
_cell_length_c                   23.548(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2143.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    3864
_cell_measurement_theta_min      1.80
_cell_measurement_theta_max      28.29

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.995
_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            7105
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.730
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1895
_reflns_number_gt                1183
_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)+(0.0630P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0093(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1895
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_restrained_S_all      0.889
_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
O1 O 0.25245(19) 0.11605(15) 0.48163(7) 0.0297(4) Uani 1 1 d . . . . .
O6 O 0.6963(2) 0.05956(15) 0.58234(8) 0.0321(4) Uani 1 1 d . . . . .
H6A H 0.7029 0.0043 0.5589 0.078(13) Uiso 1 1 calc R . . . .
O3 O 0.43549(19) 0.23363(15) 0.58456(7) 0.0312(4) Uani 1 1 d . . . . .
O2 O 0.1524(2) -0.01855(14) 0.54169(8) 0.0330(5) Uani 1 1 d . . . . .
O4 O 0.4995(3) 0.40216(15) 0.62875(8) 0.0369(5) Uani 1 1 d . . . . .
H4 H 0.4503 0.4311 0.6005 0.088(14) Uiso 1 1 calc R . . . .
O5 O 0.5017(2) -0.05666(15) 0.62234(8) 0.0373(5) Uani 1 1 d . . . . .
C4 C 0.5644(3) 0.2270(2) 0.67608(10) 0.0265(6) Uani 1 1 d . . . . .
C9 C 0.6011(3) 0.1064(2) 0.67541(10) 0.0262(6) Uani 1 1 d . . . . .
C1 C 0.1658(3) 0.0852(2) 0.52420(11) 0.0277(6) Uani 1 1 d . . . . .
C3 C 0.4954(3) 0.2868(2) 0.62532(11) 0.0280(5) Uani 1 1 d . . . . .
C8 C 0.6530(3) 0.0518(2) 0.72527(11) 0.0320(6) Uani 1 1 d . . . . .
H8 H 0.6783 -0.0294 0.7248 0.048(8) Uiso 1 1 calc R . . . .
N1 N 0.0992(2) 0.29677(17) 0.53108(9) 0.0295(5) Uani 1 1 d . . . . .
H1A H 0.0634 0.2980 0.4944 0.059(10) Uiso 1 1 calc R . . . .
H1B H 0.2109 0.3134 0.5323 0.050(9) Uiso 1 1 calc R . . . .
H1C H 0.0416 0.3511 0.5515 0.050(9) Uiso 1 1 calc R . . . .
C2 C 0.0696(3) 0.1791(2) 0.55557(11) 0.0282(6) Uani 1 1 d . . . . .
H2A H -0.0520 0.1611 0.5540 0.025(6) Uiso 1 1 calc R . . . .
H2B H 0.1040 0.1791 0.5960 0.039(8) Uiso 1 1 calc R . . . .
C5 C 0.5797(3) 0.2880(2) 0.72714(11) 0.0311(6) Uani 1 1 d . . . . .
H5 H 0.5541 0.3692 0.7281 0.039(8) Uiso 1 1 calc R . . . .
C10 C 0.5921(3) 0.0306(2) 0.62345(11) 0.0292(6) Uani 1 1 d . . . . .
C7 C 0.6685(3) 0.1139(2) 0.77584(12) 0.0348(6) Uani 1 1 d . . . . .
H7 H 0.7040 0.0754 0.8095 0.043(8) Uiso 1 1 calc R . . . .
C6 C 0.6314(3) 0.2328(2) 0.77661(12) 0.0343(6) Uani 1 1 d . . . . .
H6 H 0.6415 0.2761 0.8109 0.044(8) Uiso 1 1 calc R . . . .


_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
O1 C1 1.267(3) . ?
O6 C10 1.317(3) . ?
O6 H6A 0.8400 . ?
O3 C3 1.232(3) . ?
O2 C1 1.259(3) . ?
O4 C3 1.321(3) . ?
O4 H4 0.8400 . ?
O5 C10 1.230(3) . ?
C4 C5 1.395(4) . ?
C4 C9 1.409(4) . ?
C4 C3 1.482(4) . ?
C9 C8 1.392(4) . ?
C9 C10 1.501(4) . ?
C1 C2 1.512(3) . ?
C8 C7 1.392(4) . ?
C8 H8 0.9500 . ?
N1 C2 1.482(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 C6 1.387(4) . ?
C5 H5 0.9500 . ?
C7 C6 1.391(4) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?

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
C10 O6 H6A 109.5 . . ?
C3 O4 H4 109.5 . . ?
C5 C4 C9 118.7(2) . . ?
C5 C4 C3 119.8(2) . . ?
C9 C4 C3 121.3(2) . . ?
C8 C9 C4 119.4(2) . . ?
C8 C9 C10 116.3(2) . . ?
C4 C9 C10 124.3(2) . . ?
O2 C1 O1 124.5(2) . . ?
O2 C1 C2 117.8(2) . . ?
O1 C1 C2 117.7(2) . . ?
O3 C3 O4 123.3(2) . . ?
O3 C3 C4 123.0(2) . . ?
O4 C3 C4 113.7(2) . . ?
C7 C8 C9 121.3(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N1 C2 C1 111.95(19) . . ?
N1 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C6 C5 C4 121.5(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
O5 C10 O6 123.8(2) . . ?
O5 C10 C9 120.9(2) . . ?
O6 C10 C9 115.1(2) . . ?
C6 C7 C8 119.4(3) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?

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
C5 C4 C9 C8 -0.6(3) . . . . ?
C3 C4 C9 C8 -174.9(2) . . . . ?
C5 C4 C9 C10 -179.2(2) . . . . ?
C3 C4 C9 C10 6.5(3) . . . . ?
C5 C4 C3 O3 -159.3(2) . . . . ?
C9 C4 C3 O3 14.9(3) . . . . ?
C5 C4 C3 O4 18.6(3) . . . . ?
C9 C4 C3 O4 -167.1(2) . . . . ?
C4 C9 C8 C7 0.3(3) . . . . ?
C10 C9 C8 C7 179.0(2) . . . . ?
O2 C1 C2 N1 179.0(2) . . . . ?
O1 C1 C2 N1 -2.0(3) . . . . ?
C9 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C5 C6 175.0(2) . . . . ?
C8 C9 C10 O5 58.8(3) . . . . ?
C4 C9 C10 O5 -122.6(3) . . . . ?
C8 C9 C10 O6 -116.2(2) . . . . ?
C4 C9 C10 O6 62.4(3) . . . . ?
C9 C8 C7 C6 0.0(4) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C8 C7 C6 C5 0.0(4) . . . . ?

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
O4 H4 O2 0.84 1.71 2.547(3) 176.5 7_665
O6 H6A O1 0.84 1.71 2.543(2) 169.5 5_656
N1 H1A O3 0.91 2.15 3.039(3) 165.2 3_456
N1 H1B O3 0.91 2.35 3.045(3) 132.7 .
N1 H1B O2 0.91 2.22 2.903(3) 131.6 7_665
N1 H1C O5 0.91 2.00 2.841(3) 152.4 7_665

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_gph100K
_database_code_depnum_ccdc_archive 'CCDC 1437193'
_audit_update_record             
;
2016-06-01 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-phthalic acid (1:1)'
_chemical_name_common            'glycine-phthalic acid (1:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 O4, C2 H5 N O2'
_chemical_formula_sum            'C10 H11 N O6'
_chemical_formula_weight         241.20

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.9445(11)
_cell_length_b                   11.4431(14)
_cell_length_c                   23.524(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2138.5(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3642
_cell_measurement_theta_min      1.77
_cell_measurement_theta_max      27.89

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.995
_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            6921
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.094
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1891
_reflns_number_gt                1141
_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)+(0.0649P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0115(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1891
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1151
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_restrained_S_all      0.894
_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
O1 O 0.2529(2) 0.11600(16) 0.48159(8) 0.0290(5) Uani 1 1 d . . . . .
O6 O 0.6954(2) 0.05991(17) 0.58200(9) 0.0307(5) Uani 1 1 d . . . . .
H6A H 0.7044 0.0038 0.5592 0.076(15) Uiso 1 1 calc R . . . .
O3 O 0.4351(2) 0.23413(17) 0.58453(9) 0.0307(5) Uani 1 1 d . . . . .
O2 O 0.1517(2) -0.01822(17) 0.54177(9) 0.0316(5) Uani 1 1 d . . . . .
O4 O 0.5012(3) 0.40241(16) 0.62877(9) 0.0342(5) Uani 1 1 d . . . . .
H4 H 0.4494 0.4316 0.6011 0.087(16) Uiso 1 1 calc R . . . .
O5 O 0.5011(2) -0.05661(17) 0.62231(9) 0.0347(5) Uani 1 1 d . . . . .
C4 C 0.5651(3) 0.2271(2) 0.67615(11) 0.0257(6) Uani 1 1 d . . . . .
C9 C 0.6013(3) 0.1064(2) 0.67534(12) 0.0251(6) Uani 1 1 d . . . . .
C1 C 0.1658(3) 0.0857(2) 0.52400(13) 0.0281(7) Uani 1 1 d . . . . .
C3 C 0.4963(3) 0.2867(2) 0.62526(13) 0.0276(6) Uani 1 1 d . . . . .
C8 C 0.6526(3) 0.0518(3) 0.72544(13) 0.0308(7) Uani 1 1 d . . . . .
H8 H 0.6773 -0.0294 0.7250 0.052(10) Uiso 1 1 calc R . . . .
N1 N 0.0994(3) 0.29690(19) 0.53117(11) 0.0284(6) Uani 1 1 d . . . . .
H1A H 0.0626 0.2983 0.4945 0.054(11) Uiso 1 1 calc R . . . .
H1B H 0.2115 0.3131 0.5321 0.035(8) Uiso 1 1 calc R . . . .
H1C H 0.0425 0.3514 0.5518 0.052(10) Uiso 1 1 calc R . . . .
C2 C 0.0692(3) 0.1794(2) 0.55574(13) 0.0266(6) Uani 1 1 d . . . . .
H2A H -0.0526 0.1615 0.5542 0.023(7) Uiso 1 1 calc R . . . .
H2B H 0.1040 0.1792 0.5962 0.041(9) Uiso 1 1 calc R . . . .
C5 C 0.5805(3) 0.2884(3) 0.72733(13) 0.0295(7) Uani 1 1 d . . . . .
H5 H 0.5555 0.3696 0.7282 0.047(10) Uiso 1 1 calc R . . . .
C10 C 0.5918(3) 0.0307(2) 0.62367(13) 0.0286(6) Uani 1 1 d . . . . .
C7 C 0.6684(3) 0.1140(3) 0.77608(13) 0.0331(7) Uani 1 1 d . . . . .
H7 H 0.7039 0.0755 0.8098 0.029(8) Uiso 1 1 calc R . . . .
C6 C 0.6318(3) 0.2329(3) 0.77694(13) 0.0318(7) Uani 1 1 d . . . . .
H6 H 0.6418 0.2759 0.8113 0.042(9) Uiso 1 1 calc R . . . .


_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
O1 C1 1.263(3) . ?
O6 C10 1.323(3) . ?
O6 H6A 0.8400 . ?
O3 C3 1.231(3) . ?
O2 C1 1.265(3) . ?
O4 C3 1.327(3) . ?
O4 H4 0.8400 . ?
O5 C10 1.233(3) . ?
C4 C5 1.399(4) . ?
C4 C9 1.411(4) . ?
C4 C3 1.482(4) . ?
C9 C8 1.395(4) . ?
C9 C10 1.494(4) . ?
C1 C2 1.515(4) . ?
C8 C7 1.393(4) . ?
C8 H8 0.9500 . ?
N1 C2 1.483(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 C6 1.390(4) . ?
C5 H5 0.9500 . ?
C7 C6 1.392(4) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?

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
C10 O6 H6A 109.5 . . ?
C3 O4 H4 109.5 . . ?
C5 C4 C9 119.0(3) . . ?
C5 C4 C3 119.8(3) . . ?
C9 C4 C3 121.0(2) . . ?
C8 C9 C4 119.1(3) . . ?
C8 C9 C10 116.2(3) . . ?
C4 C9 C10 124.6(2) . . ?
O1 C1 O2 124.6(3) . . ?
O1 C1 C2 118.2(2) . . ?
O2 C1 C2 117.2(2) . . ?
O3 C3 O4 123.2(3) . . ?
O3 C3 C4 123.3(2) . . ?
O4 C3 C4 113.4(3) . . ?
C7 C8 C9 121.3(3) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N1 C2 C1 111.6(2) . . ?
N1 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
O5 C10 O6 123.3(3) . . ?
O5 C10 C9 121.4(3) . . ?
O6 C10 C9 115.2(2) . . ?
C6 C7 C8 119.5(3) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?

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
C5 C4 C9 C8 -0.4(4) . . . . ?
C3 C4 C9 C8 -174.7(2) . . . . ?
C5 C4 C9 C10 -179.3(2) . . . . ?
C3 C4 C9 C10 6.4(4) . . . . ?
C5 C4 C3 O3 -158.9(3) . . . . ?
C9 C4 C3 O3 15.4(4) . . . . ?
C5 C4 C3 O4 18.7(3) . . . . ?
C9 C4 C3 O4 -167.0(2) . . . . ?
C4 C9 C8 C7 0.1(4) . . . . ?
C10 C9 C8 C7 179.1(2) . . . . ?
O1 C1 C2 N1 -1.8(3) . . . . ?
O2 C1 C2 N1 179.0(2) . . . . ?
C9 C4 C5 C6 0.4(4) . . . . ?
C3 C4 C5 C6 174.8(2) . . . . ?
C8 C9 C10 O5 58.5(3) . . . . ?
C4 C9 C10 O5 -122.6(3) . . . . ?
C8 C9 C10 O6 -117.1(3) . . . . ?
C4 C9 C10 O6 61.8(3) . . . . ?
C9 C8 C7 C6 0.2(4) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C8 C7 C6 C5 -0.2(4) . . . . ?

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
O4 H4 O2 0.84 1.71 2.548(3) 175.6 7_665
O6 H6A O1 0.84 1.71 2.541(3) 171.8 5_656
N1 H1A O3 0.91 2.15 3.039(3) 165.3 3_456
N1 H1B O3 0.91 2.34 3.034(3) 132.5 .
N1 H1B O2 0.91 2.23 2.907(3) 131.0 7_665
N1 H1C O5 0.91 1.99 2.836(3) 153.0 7_665

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.061

