# 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_gph019GPa
_database_code_depnum_ccdc_archive 'CCDC 1450716'
_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                   8.0021(7)
_cell_length_b                   11.3125(10)
_cell_length_c                   23.562(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2132.9(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_pressure       190000
_cell_measurement_reflns_used    1501
_cell_measurement_theta_min      3.0630
_cell_measurement_theta_max      27.6090

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_correction_T_min  0.389
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_process_details   'Absorb-7 (Angel, 2013)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         190000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.3457
_diffrn_reflns_number            14147
_diffrn_reflns_av_unetI/netI     0.1540
_diffrn_reflns_av_R_equivalents  0.2231
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.077
_diffrn_reflns_theta_max         28.313
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.554
_diffrn_measured_fraction_theta_full 0.617
_diffrn_reflns_Laue_measured_fraction_max 0.554
_diffrn_reflns_Laue_measured_fraction_full 0.617
_diffrn_reflns_point_group_measured_fraction_max 0.554
_diffrn_reflns_point_group_measured_fraction_full 0.617
_reflns_number_total             1473
_reflns_number_gt                597
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_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)+(0.0801P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1473
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2069
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.2052
_refine_ls_wR_factor_gt          0.1516
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_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 0.2517(4) 0.1150(3) 0.4814(3) 0.048(3) Uani 1 1 d . . . . .
O6 O 0.6999(5) 0.0595(3) 0.5850(3) 0.056(3) Uani 1 1 d . . . . .
H6A H 0.7046 0.0069 0.5611 0.067 Uiso 1 1 calc R U . . .
O3 O 0.4370(5) 0.2324(3) 0.5862(3) 0.049(3) Uani 1 1 d . . . . .
O2 O 0.1555(4) -0.0187(3) 0.5413(3) 0.053(3) Uani 1 1 d . . . . .
O4 O 0.4926(6) 0.4024(3) 0.6302(3) 0.064(3) Uani 1 1 d . . . . .
H4 H 0.4403 0.4304 0.6035 0.077 Uiso 1 1 calc R U . . .
O5 O 0.5071(5) -0.0560(3) 0.6228(3) 0.068(3) Uani 1 1 d . . . . .
C4 C 0.5630(6) 0.2276(5) 0.6779(5) 0.036(4) Uani 1 1 d . . . . .
C9 C 0.6032(7) 0.1067(4) 0.6769(5) 0.039(4) Uani 1 1 d . . . . .
C1 C 0.1677(6) 0.0849(4) 0.5248(5) 0.0389(15) Uiso 1 1 d . . . . .
C3 C 0.4933(7) 0.2856(5) 0.6263(5) 0.040(4) Uani 1 1 d . . . . .
C8 C 0.6575(8) 0.0535(5) 0.7260(6) 0.050(5) Uani 1 1 d . . . . .
H8 H 0.6863 -0.0261 0.7252 0.060 Uiso 1 1 calc R U . . .
N1 N 0.0959(5) 0.2979(3) 0.5300(3) 0.0434(12) Uiso 1 1 d . . . . .
H1A H 0.0843 0.2951 0.4925 0.065 Uiso 1 1 calc R U . . .
H1B H 0.1980 0.3235 0.5386 0.065 Uiso 1 1 calc R U . . .
H1C H 0.0203 0.3469 0.5446 0.065 Uiso 1 1 calc R U . . .
C2 C 0.0715(6) 0.1788(3) 0.5539(4) 0.044(4) Uani 1 1 d . . . . .
H2A H -0.0464 0.1592 0.5521 0.053 Uiso 1 1 calc R U . . .
H2B H 0.1034 0.1800 0.5936 0.053 Uiso 1 1 calc R U . . .
C5 C 0.5758(7) 0.2884(6) 0.7280(6) 0.048(4) Uani 1 1 d . . . . .
H5 H 0.5474 0.3681 0.7289 0.058 Uiso 1 1 calc R U . . .
C10 C 0.5941(8) 0.0300(4) 0.6244(5) 0.047(4) Uani 1 1 d . . . . .
C7 C 0.6706(7) 0.1143(5) 0.7760(5) 0.054(4) Uani 1 1 d . . . . .
H7 H 0.7061 0.0763 0.8089 0.065 Uiso 1 1 calc R U . . .
C6 C 0.6300(8) 0.2340(6) 0.7770(5) 0.058(4) Uani 1 1 d . . . . .
H6 H 0.6393 0.2770 0.8105 0.070 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.270(11) . ?
O6 C10 1.300(11) . ?
O6 H6A 0.8200 . ?
O3 C3 1.207(10) . ?
O2 C1 1.239(7) . ?
O4 C3 1.325(6) . ?
O4 H4 0.8200 . ?
O5 C10 1.196(6) . ?
C4 C5 1.369(14) . ?
C4 C9 1.405(8) . ?
C4 C3 1.489(13) . ?
C9 C8 1.375(15) . ?
C9 C10 1.514(14) . ?
C1 C2 1.481(9) . ?
C8 C7 1.368(16) . ?
C8 H8 0.9300 . ?
N1 C2 1.473(7) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 C6 1.378(15) . ?
C5 H5 0.9300 . ?
C7 C6 1.393(9) . ?
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 119.1(10) . . ?
C5 C4 C3 120.6(7) . . ?
C9 C4 C3 120.1(9) . . ?
C8 C9 C4 119.0(10) . . ?
C8 C9 C10 116.9(6) . . ?
C4 C9 C10 124.1(10) . . ?
O2 C1 O1 123.3(6) . . ?
O2 C1 C2 119.4(8) . . ?
O1 C1 C2 117.1(5) . . ?
O3 C3 O4 123.3(8) . . ?
O3 C3 C4 124.0(6) . . ?
O4 C3 C4 112.6(8) . . ?
C7 C8 C9 121.9(7) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
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 114.2(7) . . ?
N1 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
N1 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C4 C5 C6 121.4(7) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
O5 C10 O6 124.4(9) . . ?
O5 C10 C9 121.3(9) . . ?
O6 C10 C9 113.9(6) . . ?
C8 C7 C6 118.9(11) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C5 C6 C7 119.7(11) . . ?
C5 C6 H6 120.2 . . ?
C7 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 -1.3(9) . . . . ?
C3 C4 C9 C8 -176.0(6) . . . . ?
C5 C4 C9 C10 180.0(6) . . . . ?
C3 C4 C9 C10 5.4(9) . . . . ?
C5 C4 C3 O3 -159.3(7) . . . . ?
C9 C4 C3 O3 15.2(11) . . . . ?
C5 C4 C3 O4 17.8(9) . . . . ?
C9 C4 C3 O4 -167.7(6) . . . . ?
C4 C9 C8 C7 1.3(11) . . . . ?
C10 C9 C8 C7 -180.0(6) . . . . ?
O2 C1 C2 N1 -179.7(7) . . . . ?
O1 C1 C2 N1 -3.7(10) . . . . ?
C9 C4 C5 C6 1.2(10) . . . . ?
C3 C4 C5 C6 175.8(6) . . . . ?
C8 C9 C10 O5 60.0(8) . . . . ?
C4 C9 C10 O5 -121.3(8) . . . . ?
C8 C9 C10 O6 -113.4(8) . . . . ?
C4 C9 C10 O6 65.3(8) . . . . ?
C9 C8 C7 C6 -1.0(11) . . . . ?
C4 C5 C6 C7 -0.9(11) . . . . ?
C8 C7 C6 C5 0.7(11) . . . . ?

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 2.567(9) 173.5 7_665
O6 H6A O1 0.82 1.74 2.548(7) 168.4 5_656
N1 H1A O3 0.89 2.22 3.040(10) 153.0 3_456
N1 H1B O3 0.89 2.44 3.122(6) 133.2 .
N1 H1B O2 0.89 2.14 2.887(5) 141.5 7_665
N1 H1C O5 0.89 2.16 2.862(9) 135.7 7_665

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_gph050GPa
_database_code_depnum_ccdc_archive 'CCDC 1450717'
_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                   7.8988(8)
_cell_length_b                   11.3424(12)
_cell_length_c                   23.327(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2089.9(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_pressure       500000
_cell_measurement_reflns_used    1547
_cell_measurement_theta_min      3.1010
_cell_measurement_theta_max      25.7220

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.129
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_correction_T_min  0.387
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_process_details   'Absorb-7 (Angel, 2013)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         500000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.3457
_diffrn_reflns_number            13858
_diffrn_reflns_av_unetI/netI     0.1302
_diffrn_reflns_av_R_equivalents  0.1984
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.115
_diffrn_reflns_theta_max         28.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.546
_diffrn_measured_fraction_theta_full 0.610
_diffrn_reflns_Laue_measured_fraction_max 0.546
_diffrn_reflns_Laue_measured_fraction_full 0.610
_diffrn_reflns_point_group_measured_fraction_max 0.546
_diffrn_reflns_point_group_measured_fraction_full 0.610
_reflns_number_total             1425
_reflns_number_gt                595
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_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)+(0.1112P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1425
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1999
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.2431
_refine_ls_wR_factor_gt          0.1747
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.2528(4) 0.1152(3) 0.4822(3) 0.047(3) Uani 1 1 d . . . . .
O6 O 0.6984(6) 0.0606(3) 0.5843(4) 0.054(3) Uani 1 1 d . . . . .
H6A H 0.7067 0.0064 0.5612 0.065 Uiso 1 1 calc R U . . .
O3 O 0.4363(5) 0.2347(3) 0.5866(3) 0.048(3) Uani 1 1 d . . . . .
O2 O 0.1541(5) -0.0173(3) 0.5430(3) 0.061(3) Uani 1 1 d . . . . .
O4 O 0.4989(7) 0.4027(3) 0.6312(4) 0.065(3) Uani 1 1 d . . . . .
H4 H 0.4482 0.4306 0.6037 0.078 Uiso 1 1 calc R U . . .
O5 O 0.5059(6) -0.0561(3) 0.6244(3) 0.065(3) Uani 1 1 d . . . . .
C4 C 0.5669(7) 0.2273(5) 0.6779(5) 0.038(4) Uani 1 1 d . . . . .
C9 C 0.6054(7) 0.1060(5) 0.6771(5) 0.038(4) Uani 1 1 d . . . . .
C1 C 0.1660(7) 0.0859(5) 0.5241(5) 0.0413(16) Uiso 1 1 d . . . . .
C3 C 0.4960(7) 0.2870(5) 0.6280(5) 0.036(4) Uani 1 1 d . . . . .
C8 C 0.6584(8) 0.0521(6) 0.7269(6) 0.046(5) Uani 1 1 d . . . . .
H8 H 0.6839 -0.0279 0.7263 0.055 Uiso 1 1 calc R U . . .
N1 N 0.0988(6) 0.2982(3) 0.5292(4) 0.052(3) Uani 1 1 d . . . . .
H1A H 0.0647 0.2968 0.4928 0.078 Uiso 1 1 calc R U . . .
H1B H 0.2087 0.3155 0.5306 0.078 Uiso 1 1 calc R U . . .
H1C H 0.0405 0.3526 0.5483 0.078 Uiso 1 1 calc R U . . .
C2 C 0.0697(7) 0.1802(4) 0.5558(5) 0.044(4) Uani 1 1 d . . . . .
H2A H -0.0503 0.1620 0.5550 0.052 Uiso 1 1 calc R U . . .
H2B H 0.1059 0.1819 0.5955 0.052 Uiso 1 1 calc R U . . .
C5 C 0.5790(8) 0.2877(6) 0.7297(6) 0.044(4) Uani 1 1 d . . . . .
H5 H 0.5495 0.3671 0.7309 0.053 Uiso 1 1 calc R U . . .
C10 C 0.5940(8) 0.0302(5) 0.6253(5) 0.044(4) Uani 1 1 d . . . . .
C7 C 0.6745(9) 0.1129(6) 0.7770(6) 0.063(5) Uani 1 1 d . . . . .
H7 H 0.7127 0.0744 0.8098 0.075 Uiso 1 1 calc R U . . .
C6 C 0.6338(8) 0.2330(7) 0.7794(6) 0.063(5) Uani 1 1 d . . . . .
H6 H 0.6433 0.2749 0.8135 0.076 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.239(11) . ?
O6 C10 1.308(11) . ?
O6 H6A 0.8200 . ?
O3 C3 1.228(11) . ?
O2 C1 1.254(8) . ?
O4 C3 1.314(7) . ?
O4 H4 0.8200 . ?
O5 C10 1.201(7) . ?
C4 C5 1.392(15) . ?
C4 C9 1.409(9) . ?
C4 C3 1.458(14) . ?
C9 C8 1.378(16) . ?
C9 C10 1.485(15) . ?
C1 C2 1.506(10) . ?
C8 C7 1.363(17) . ?
C8 H8 0.9300 . ?
N1 C2 1.493(8) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 C6 1.385(15) . ?
C5 H5 0.9300 . ?
C7 C6 1.401(11) . ?
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 118.6(10) . . ?
C5 C4 C3 119.3(7) . . ?
C9 C4 C3 121.7(10) . . ?
C8 C9 C4 119.2(11) . . ?
C8 C9 C10 116.6(7) . . ?
C4 C9 C10 124.3(10) . . ?
O1 C1 O2 124.7(7) . . ?
O1 C1 C2 118.4(5) . . ?
O2 C1 C2 116.9(8) . . ?
O3 C3 O4 122.3(9) . . ?
O3 C3 C4 123.4(6) . . ?
O4 C3 C4 114.3(8) . . ?
C7 C8 C9 121.8(8) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
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 110.8(7) . . ?
N1 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C6 C5 C4 121.8(8) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
O5 C10 O6 124.6(9) . . ?
O5 C10 C9 121.4(9) . . ?
O6 C10 C9 113.8(6) . . ?
C8 C7 C6 120.3(12) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C5 C6 C7 118.4(12) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?

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 -1.9(9) . . . . ?
C3 C4 C9 C8 -174.5(6) . . . . ?
C5 C4 C9 C10 178.5(6) . . . . ?
C3 C4 C9 C10 6.0(10) . . . . ?
C5 C4 C3 O3 -158.5(7) . . . . ?
C9 C4 C3 O3 14.0(12) . . . . ?
C5 C4 C3 O4 20.6(10) . . . . ?
C9 C4 C3 O4 -166.9(6) . . . . ?
C4 C9 C8 C7 0.1(11) . . . . ?
C10 C9 C8 C7 179.7(7) . . . . ?
O1 C1 C2 N1 -0.1(11) . . . . ?
O2 C1 C2 N1 178.8(7) . . . . ?
C9 C4 C5 C6 2.5(11) . . . . ?
C3 C4 C5 C6 175.3(6) . . . . ?
C8 C9 C10 O5 58.1(9) . . . . ?
C4 C9 C10 O5 -122.4(8) . . . . ?
C8 C9 C10 O6 -116.1(8) . . . . ?
C4 C9 C10 O6 63.4(8) . . . . ?
C9 C8 C7 C6 1.2(12) . . . . ?
C4 C5 C6 C7 -1.2(11) . . . . ?
C8 C7 C6 C5 -0.7(11) . . . . ?

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 1.73 2.553(9) 176.4 7_665
O6 H6A O1 0.82 1.74 2.556(7) 172.3 5_656
N1 H1A O3 0.89 2.14 3.014(11) 166.0 3_456
N1 H1B O3 0.89 2.40 3.069(7) 131.6 .
N1 H1B O2 0.89 2.20 2.880(5) 132.4 7_665
N1 H1C O5 0.89 2.09 2.890(10) 149.5 7_665

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.063

