# Electronic Supplementary Material (ESI) for RSC Sustainability.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_Urea_4HBA
_database_code_depnum_ccdc_archive 'CCDC 2190718'
loop_
_audit_author_name
_audit_author_address
'Dr. Ranjit Thakuria'
;Gauhati University
India
;
_audit_update_record             
;
2022-07-16 deposited with the CCDC.	2023-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Urea 4-hydroxybenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 N2 O7'
_chemical_formula_sum            'C15 H16 N2 O7'
_chemical_formula_weight         336.30

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

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

_cell_length_a                   6.8062(12)
_cell_length_b                   6.5343(11)
_cell_length_c                   18.326(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.585(4)
_cell_angle_gamma                90
_cell_volume                     807.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1934
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      23.78

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6596
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.242
_diffrn_reflns_theta_max         26.447
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1659
_reflns_number_gt                1210
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0706P)²+0.1461P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.016(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1659
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.1642(2) 0.2767(2) 0.51875(8) 0.0579(4) Uani 1 1 d . . . . .
C1 C 0.4605(3) 0.3891(3) 0.58792(9) 0.0394(4) Uani 1 1 d . . . . .
C2 C 0.5759(3) 0.5468(3) 0.62070(10) 0.0441(5) Uani 1 1 d . . . . .
H2 H 0.524195 0.678657 0.619842 0.053 Uiso 1 1 calc R U . . .
O2 O 0.18387(19) 0.6044(2) 0.55250(7) 0.0528(4) Uani 1 1 d . . . . .
C3 C 0.7655(3) 0.5122(3) 0.65451(10) 0.0427(5) Uani 1 1 d . . . . .
H3 H 0.840730 0.619715 0.676583 0.051 Uiso 1 1 calc R U . . .
O3 O 1.0309(2) 0.2766(2) 0.68713(9) 0.0615(5) Uani 1 1 d . . . . .
C4 C 0.8436(3) 0.3173(3) 0.65555(10) 0.0443(5) Uani 1 1 d . . . . .
O4 O 0.250000 0.5727(3) 0.750000 0.0488(5) Uani 1 2 d S T P . .
N1 N 0.2927(3) 0.8686(3) 0.81231(11) 0.0547(5) Uani 1 1 d . . . . .
C5 C 0.7299(3) 0.1575(3) 0.62275(13) 0.0592(6) Uani 1 1 d . . . . .
H5 H 0.781985 0.025841 0.623359 0.071 Uiso 1 1 calc R U . . .
C6 C 0.5401(3) 0.1941(3) 0.58937(12) 0.0523(5) Uani 1 1 d . . . . .
H6 H 0.464385 0.086598 0.567523 0.063 Uiso 1 1 calc R U . . .
C7 C 0.2585(3) 0.4335(3) 0.55202(9) 0.0431(5) Uani 1 1 d . . . . .
C8 C 0.250000 0.7643(4) 0.750000 0.0399(6) Uani 1 2 d S T P . .
H3A H 1.095(4) 0.395(4) 0.7083(13) 0.076(7) Uiso 1 1 d . . . . .
H1A H 0.311(4) 0.804(4) 0.8484(13) 0.057(7) Uiso 1 1 d . . . . .
H1B H 0.313(3) 0.998(4) 0.8080(12) 0.062(7) Uiso 1 1 d . . . . .
H1C H 0.051(5) 0.321(4) 0.4968(16) 0.084(9) Uiso 1 1 d . . . . .


_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 C7 1.316(2) . ?
O1 H1C 0.87(3) . ?
C1 C6 1.383(3) . ?
C1 C2 1.384(3) . ?
C1 C7 1.472(3) . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
O2 C7 1.227(2) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
O3 C4 1.355(2) . ?
O3 H3A 0.95(3) . ?
C4 C5 1.389(3) . ?
O4 C8 1.252(3) . ?
N1 C8 1.329(2) . ?
N1 H1A 0.78(2) . ?
N1 H1B 0.86(3) . ?
C5 C6 1.375(3) . ?
C5 H5 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
C7 O1 H1C 107.6(18) . . ?
C6 C1 C2 118.64(17) . . ?
C6 C1 C7 122.01(17) . . ?
C2 C1 C7 119.35(17) . . ?
C3 C2 C1 121.23(17) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.70(16) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C4 O3 H3A 111.7(16) . . ?
O3 C4 C3 121.79(16) . . ?
O3 C4 C5 118.43(17) . . ?
C3 C4 C5 119.78(17) . . ?
C8 N1 H1A 116.4(17) . . ?
C8 N1 H1B 116.4(15) . . ?
H1A N1 H1B 127(2) . . ?
C6 C5 C4 119.91(19) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.74(18) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O2 C7 O1 122.33(17) . . ?
O2 C7 C1 122.63(17) . . ?
O1 C7 C1 115.04(17) . . ?
O4 C8 N1 120.87(13) . 2_556 ?
O4 C8 N1 120.87(13) . . ?
N1 C8 N1 118.3(3) 2_556 . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.039



####################################################################### 
# 
# 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_Urea_25DHBA
_database_code_depnum_ccdc_archive 'CCDC 2190720'
loop_
_audit_author_name
_audit_author_address
'Dr. Ranjit Thakuria'
;Gauhati University
India
;
_audit_update_record             
;
2022-07-16 deposited with the CCDC.	2023-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Urea 2,5-dihydroxybenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H10 N2 O5'
_chemical_formula_sum            'C8 H10 N2 O5'
_chemical_formula_weight         214.18

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   4.7778(4)
_cell_length_b                   8.5865(6)
_cell_length_c                   11.3523(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.919(4)
_cell_angle_gamma                90
_cell_volume                     463.24(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6206
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      26.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_F_000             224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.129
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4924
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.803
_diffrn_reflns_theta_max         26.966
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measured_fraction_theta_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             1605
_reflns_number_gt                1522
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_max     0.930
_reflns_Friedel_fraction_full    0.973

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1049P)²+0.1386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.12(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -1(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1605
_refine_ls_number_parameters     166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1579
_refine_ls_wR_factor_gt          0.1446
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.141
_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 -0.1573(8) -0.1290(4) 0.6310(3) 0.0408(8) Uani 1 1 d . . . . .
O2 O 0.4809(9) 0.1808(4) 0.9923(3) 0.0482(9) Uani 1 1 d . . . . .
O3 O 0.7467(8) 0.3150(4) 0.8315(3) 0.0412(8) Uani 1 1 d . . . . .
O4 O 0.6295(7) 0.2639(3) 0.6403(2) 0.0346(7) Uani 1 1 d . . . . .
O9 O 0.0235(7) 0.4536(4) 0.5879(3) 0.0369(7) Uani 1 1 d . . . . .
N1 N 0.3773(10) 0.6291(5) 0.6070(4) 0.0435(10) Uani 1 1 d . . . . .
N2 N 0.1803(11) 0.5395(6) 0.7707(4) 0.0458(10) Uani 1 1 d . . . . .
C1 C 0.3818(10) 0.1325(5) 0.7805(3) 0.0300(9) Uani 1 1 d . . . . .
C2 C 0.2192(10) 0.0516(5) 0.6899(3) 0.0299(9) Uani 1 1 d . . . . .
H2 H 0.250961 0.067771 0.611395 0.036 Uiso 1 1 calc R U . . .
C3 C 0.0131(10) -0.0514(5) 0.7164(4) 0.0333(9) Uani 1 1 d . . . . .
C4 C -0.0317(11) -0.0770(5) 0.8346(4) 0.0369(10) Uani 1 1 d . . . . .
H4 H -0.167968 -0.147662 0.853154 0.044 Uiso 1 1 calc R U . . .
C5 C 0.1258(11) 0.0024(5) 0.9235(4) 0.0393(11) Uani 1 1 d . . . . .
H5 H 0.091615 -0.013968 1.001737 0.047 Uiso 1 1 calc R U . . .
C6 C 0.3351(11) 0.1067(5) 0.8991(3) 0.0350(10) Uani 1 1 d . . . . .
C7 C 0.5996(9) 0.2447(5) 0.7527(3) 0.0302(9) Uani 1 1 d . . . . .
C8 C 0.1888(9) 0.5399(5) 0.6534(3) 0.0312(8) Uani 1 1 d . . . . .
H1A H -0.080(12) -0.101(6) 0.558(6) 0.045(14) Uiso 1 1 d . . . . .
H1C H 0.520(15) 0.678(8) 0.664(6) 0.057(18) Uiso 1 1 d . . . . .
H1D H 0.331(14) 0.636(8) 0.538(6) 0.053(17) Uiso 1 1 d . . . . .
H2A H 0.288(14) 0.588(7) 0.816(5) 0.048(17) Uiso 1 1 d . . . . .
H2B H 0.075(10) 0.474(6) 0.796(4) 0.021(11) Uiso 1 1 d . . . . .
H2C H 0.657(18) 0.239(10) 0.951(8) 0.08(2) Uiso 1 1 d . . . . .
H4A H 0.767(18) 0.335(10) 0.627(7) 0.08(2) Uiso 1 1 d . . . . .


_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 C3 1.372(6) . ?
O1 H1A 0.97(6) . ?
O2 C6 1.363(6) . ?
O2 H2C 1.13(9) . ?
O3 C7 1.237(5) . ?
O4 C7 1.309(5) . ?
O4 H4A 0.92(9) . ?
O9 C8 1.267(5) . ?
N1 C8 1.331(6) . ?
N1 H1C 0.98(7) . ?
N1 H1D 0.80(7) . ?
N2 C8 1.336(6) . ?
N2 H2A 0.81(7) . ?
N2 H2B 0.83(5) . ?
C1 C6 1.404(5) . ?
C1 C2 1.407(6) . ?
C1 C7 1.475(6) . ?
C2 C3 1.380(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(6) . ?
C4 C5 1.376(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(7) . ?
C5 H5 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
C3 O1 H1A 104(4) . . ?
C6 O2 H2C 103(4) . . ?
C7 O4 H4A 113(5) . . ?
C8 N1 H1C 116(4) . . ?
C8 N1 H1D 108(5) . . ?
H1C N1 H1D 136(6) . . ?
C8 N2 H2A 124(4) . . ?
C8 N2 H2B 116(3) . . ?
H2A N2 H2B 120(5) . . ?
C6 C1 C2 119.5(4) . . ?
C6 C1 C7 119.5(4) . . ?
C2 C1 C7 121.0(3) . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
O1 C3 C2 122.9(4) . . ?
O1 C3 C4 117.6(4) . . ?
C2 C3 C4 119.5(4) . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.5(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
O2 C6 C5 117.8(3) . . ?
O2 C6 C1 123.5(4) . . ?
C5 C6 C1 118.8(4) . . ?
O3 C7 O4 122.2(4) . . ?
O3 C7 C1 121.7(4) . . ?
O4 C7 C1 116.2(4) . . ?
O9 C8 N1 120.7(4) . . ?
O9 C8 N2 120.1(4) . . ?
N1 C8 N2 119.2(4) . . ?

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
C6 C1 C2 C3 0.6(6) . . . . ?
C7 C1 C2 C3 -179.1(4) . . . . ?
C1 C2 C3 O1 177.7(4) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
O1 C3 C4 C5 -177.5(4) . . . . ?
C2 C3 C4 C5 1.2(6) . . . . ?
C3 C4 C5 C6 -1.3(7) . . . . ?
C4 C5 C6 O2 179.9(4) . . . . ?
C4 C5 C6 C1 1.0(7) . . . . ?
C2 C1 C6 O2 -179.4(4) . . . . ?
C7 C1 C6 O2 0.2(6) . . . . ?
C2 C1 C6 C5 -0.7(6) . . . . ?
C7 C1 C6 C5 179.0(4) . . . . ?
C6 C1 C7 O3 1.3(6) . . . . ?
C2 C1 C7 O3 -179.0(4) . . . . ?
C6 C1 C7 O4 -179.4(4) . . . . ?
C2 C1 C7 O4 0.3(6) . . . . ?

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.090



####################################################################### 
# 
# 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_Urea_26DHBA
_database_code_depnum_ccdc_archive 'CCDC 2190721'
loop_
_audit_author_name
_audit_author_address
'Dr. Ranjit Thakuria'
;Gauhati University
India
;
_audit_update_record             
;
2022-07-16 deposited with the CCDC.	2023-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Urea 2,6-dihydroxybenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 O4, C H5 N2 O'
_chemical_formula_sum            'C8 H10 N2 O5'
_chemical_formula_weight         214.18

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

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

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

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

_cell_length_a                   6.8879(5)
_cell_length_b                   13.7039(11)
_cell_length_c                   10.2098(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.004(5)
_cell_angle_gamma                90
_cell_volume                     961.36(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1764
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.33

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8009
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.973
_diffrn_reflns_theta_max         26.415
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1963
_reflns_number_gt                1308
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0835P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1963
_refine_ls_number_parameters     169
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1536
_refine_ls_wR_factor_gt          0.1375
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.075
_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
C1 C 0.6769(3) 0.82010(14) 0.32253(17) 0.0355(5) Uani 1 1 d . . . . .
C2 C 1.0075(3) 0.62398(14) 0.32220(17) 0.0365(5) Uani 1 1 d . . . . .
C3 C 0.9290(3) 0.58152(14) 0.20468(18) 0.0408(5) Uani 1 1 d . . . . .
C4 C 0.7598(3) 0.52765(18) 0.2019(2) 0.0571(6) Uani 1 1 d . . . . .
H4 H 0.709640 0.498894 0.124249 0.069 Uiso 1 1 calc R U . . .
C5 C 0.6673(4) 0.5172(2) 0.3148(3) 0.0728(8) Uani 1 1 d . . . . .
H5 H 0.552971 0.480939 0.312598 0.087 Uiso 1 1 calc R U . . .
C6 C 0.7364(4) 0.5582(2) 0.4317(2) 0.0678(7) Uani 1 1 d . . . . .
H6 H 0.669366 0.550400 0.506943 0.081 Uiso 1 1 calc R U . . .
C7 C 0.9077(3) 0.61131(16) 0.43543(19) 0.0456(5) Uani 1 1 d . . . . .
C8 C 1.1883(3) 0.68158(16) 0.3251(2) 0.0473(5) Uani 1 1 d . . . . .
H1A H 0.889(4) 0.872(2) 0.237(3) 0.081(8) Uiso 1 1 d . . . . .
H4A H 1.134(6) 0.637(3) 0.114(4) 0.145(14) Uiso 1 1 d . . . . .
H5A H 1.098(5) 0.687(2) 0.530(3) 0.106(11) Uiso 1 1 d . . . . .
H1B H 0.893(4) 0.896(2) 0.398(3) 0.094(10) Uiso 1 1 d . . . . .
N1 N 0.8424(3) 0.86750(15) 0.3217(2) 0.0535(5) Uani 1 1 d . . . . .
N2A N 0.6000(2) 0.78386(13) 0.21523(15) 0.0525(6) Uani 0.495(2) 1 d D . P A 1
N2B N 0.5912(3) 0.81233(14) 0.43015(16) 0.0605(7) Uani 0.505(2) 1 d D . P A 2
O2 O 1.2683(2) 0.69342(14) 0.21878(17) 0.0708(6) Uani 1 1 d . . . . .
O3 O 1.2575(2) 0.71709(13) 0.43172(17) 0.0664(5) Uani 1 1 d . . . . .
O4 O 1.0160(3) 0.59283(12) 0.09112(14) 0.0591(5) Uani 1 1 d . . . . .
O5 O 0.9735(3) 0.65200(13) 0.55151(14) 0.0622(5) Uani 1 1 d . . . . .
O1A O 0.6000(2) 0.78386(13) 0.21523(15) 0.0525(6) Uani 0.495(2) 1 d . . P A 1
O1B O 0.5912(3) 0.81233(14) 0.43015(16) 0.0605(7) Uani 0.505(2) 1 d . . P A 2
H2B H 0.461(3) 0.778(2) 0.428(3) 0.123(12) Uiso 1 1 d D . . . .
H2C H 0.477(3) 0.744(2) 0.219(4) 0.130(13) Uiso 1 1 d D . . . .
H2A H 0.660(6) 0.835(3) 0.515(3) 0.065(14) Uiso 0.5 1 d D . P . .
H2D H 0.684(4) 0.791(3) 0.139(2) 0.037(10) Uiso 0.5 1 d D . P . .


_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
C1 N2A 1.283(2) . ?
C1 N2B 1.288(2) . ?
C1 N1 1.313(3) . ?
C2 C7 1.397(3) . ?
C2 C3 1.407(3) . ?
C2 C8 1.473(3) . ?
C3 O4 1.351(2) . ?
C3 C4 1.378(3) . ?
C4 C5 1.363(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9300 . ?
C7 O5 1.359(2) . ?
C8 O3 1.256(3) . ?
C8 O2 1.261(3) . ?
N1 H1A 0.95(3) . ?
N1 H1B 0.92(3) . ?
N2A H2C 1.016(10) . ?
N2A H2D 1.009(10) . ?
N2B H2B 1.012(10) . ?
N2B H2A 1.008(10) . ?
O4 H4A 1.03(4) . ?
O5 H5A 1.02(4) . ?

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
N2A C1 N1 119.55(19) . . ?
N2B C1 N1 119.76(18) . . ?
C7 C2 C3 118.18(18) . . ?
C7 C2 C8 120.97(17) . . ?
C3 C2 C8 120.84(18) . . ?
O4 C3 C4 117.96(18) . . ?
O4 C3 C2 121.15(18) . . ?
C4 C3 C2 120.89(19) . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 122.5(2) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C7 118.8(2) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
O5 C7 C6 118.1(2) . . ?
O5 C7 C2 121.17(18) . . ?
C6 C7 C2 120.68(19) . . ?
O3 C8 O2 122.3(2) . . ?
O3 C8 C2 119.6(2) . . ?
O2 C8 C2 118.13(19) . . ?
C1 N1 H1A 112.9(17) . . ?
C1 N1 H1B 119(2) . . ?
H1A N1 H1B 128(3) . . ?
C1 N2A H2C 118(2) . . ?
C1 N2A H2D 113(2) . . ?
H2C N2A H2D 128(3) . . ?
C1 N2B H2B 119(2) . . ?
C1 N2B H2A 120(3) . . ?
H2B N2B H2A 121(3) . . ?
C3 O4 H4A 105(2) . . ?
C7 O5 H5A 104.1(17) . . ?

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.067



####################################################################### 
# 
# 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_Urea_24DHBA
_database_code_depnum_ccdc_archive 'CCDC 2190719'
loop_
_audit_author_name
_audit_author_address
'Dr. Ranjit Thakuria'
;Gauhati University
India
;
_audit_update_record             
;
2022-07-16 deposited with the CCDC.	2023-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Urea 2,4-dihydroxybenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 N2 O9'
_chemical_formula_sum            'C15 H16 N2 O9'
_chemical_formula_weight         368.30

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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   11.4269(9)
_cell_length_b                   29.691(2)
_cell_length_c                   5.1313(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1740.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7859
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      26.64

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18087
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.372
_diffrn_reflns_theta_max         26.705
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             1869
_reflns_number_gt                1492
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0930P)²+0.1971P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.031(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1869
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.65633(12) 0.37994(5) 0.7414(3) 0.0559(4) Uani 1 1 d . . . . .
O2 O 0.46341(13) 0.30995(5) 0.0363(3) 0.0562(4) Uani 1 1 d . . . . .
O3 O 0.57220(12) 0.45604(4) 0.9036(3) 0.0565(4) Uani 1 1 d . . . . .
O4 O 0.40421(14) 0.48135(5) 0.7369(3) 0.0648(5) Uani 1 1 d . . . . .
O5 O 0.63285(17) 0.250000 1.0431(4) 0.0570(5) Uani 1 2 d S T P . .
N1 N 0.77377(18) 0.28828(6) 0.8358(4) 0.0642(5) Uani 1 1 d . . . . .
C1 C 0.48280(15) 0.41492(6) 0.5633(3) 0.0419(4) Uani 1 1 d . . . . .
C2 C 0.56709(15) 0.38046(6) 0.5684(3) 0.0410(4) Uani 1 1 d . . . . .
C3 C 0.56098(15) 0.34493(6) 0.3933(3) 0.0430(4) Uani 1 1 d . . . . .
H3 H 0.616817 0.322158 0.397808 0.052 Uiso 1 1 calc R U . . .
C4 C 0.47164(15) 0.34355(5) 0.2125(3) 0.0424(4) Uani 1 1 d . . . . .
C5 C 0.38615(15) 0.37713(6) 0.2057(3) 0.0475(4) Uani 1 1 d . . . . .
H5 H 0.325658 0.375785 0.084658 0.057 Uiso 1 1 calc R U . . .
C6 C 0.39248(15) 0.41204(6) 0.3793(3) 0.0468(4) Uani 1 1 d . . . . .
H6 H 0.335490 0.434390 0.375011 0.056 Uiso 1 1 calc R U . . .
C7 C 0.49028(16) 0.45206(6) 0.7472(3) 0.0473(4) Uani 1 1 d . . . . .
C8 C 0.7242(2) 0.250000 0.9080(5) 0.0421(5) Uani 1 2 d S T P . .
H1A H 0.839(3) 0.2875(9) 0.727(5) 0.082(8) Uiso 1 1 d . . . . .
H1B H 0.743(2) 0.3103(10) 0.879(6) 0.080(9) Uiso 1 1 d . . . . .
H1C H 0.646(2) 0.4003(11) 0.845(5) 0.092(9) Uiso 1 1 d . . . . .
H2A H 0.519(3) 0.2912(10) 0.047(5) 0.079(8) Uiso 1 1 d . . . . .
H4A H 0.413(3) 0.5032(12) 0.853(7) 0.105(10) Uiso 1 1 d . . . . .


_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 C2 1.352(2) . ?
O1 H1C 0.82(3) . ?
O2 C4 1.350(2) . ?
O2 H2A 0.85(3) . ?
O3 C7 1.239(2) . ?
O4 C7 1.314(2) . ?
O4 H4A 0.88(4) . ?
O5 C8 1.253(3) . ?
N1 C8 1.323(2) . ?
N1 H1A 0.93(3) . ?
N1 H1B 0.77(3) . ?
C1 C6 1.402(2) . ?
C1 C2 1.405(2) . ?
C1 C7 1.454(2) . ?
C2 C3 1.387(2) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(2) . ?
C5 C6 1.369(2) . ?
C5 H5 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
C2 O1 H1C 108(2) . . ?
C4 O2 H2A 112.8(19) . . ?
C7 O4 H4A 112(2) . . ?
C8 N1 H1A 119.3(16) . . ?
C8 N1 H1B 117(2) . . ?
H1A N1 H1B 124(3) . . ?
C6 C1 C2 118.21(14) . . ?
C6 C1 C7 121.79(15) . . ?
C2 C1 C7 120.00(16) . . ?
O1 C2 C3 117.02(15) . . ?
O1 C2 C1 122.51(14) . . ?
C3 C2 C1 120.47(15) . . ?
C4 C3 C2 119.68(15) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
O2 C4 C3 121.60(15) . . ?
O2 C4 C5 117.53(15) . . ?
C3 C4 C5 120.87(14) . . ?
C6 C5 C4 119.17(16) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 121.58(16) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
O3 C7 O4 121.90(15) . . ?
O3 C7 C1 122.50(16) . . ?
O4 C7 C1 115.59(16) . . ?
O5 C8 N1 120.77(13) . 7_565 ?
O5 C8 N1 120.77(13) . . ?
N1 C8 N1 118.5(3) 7_565 . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.067



