# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_BIPY-PTA
_database_code_depnum_ccdc_archive 'CCDC 1912005'
loop_
_audit_author_name
_audit_author_address
'Nikoletta Bathori'
;Cape Peninsula University of Technology
South Africa
;
_audit_update_record             
;
2019-04-24 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 N2 O4'
_chemical_formula_weight         428.47

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                   7.8077(16)
_cell_length_b                   6.1034(12)
_cell_length_c                   22.881(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.67(3)
_cell_angle_gamma                90
_cell_volume                     1089.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5002
_cell_measurement_theta_min      2.610
_cell_measurement_theta_max      28.286

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.988
_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      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Duo Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5002
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.610
_diffrn_reflns_theta_max         28.286
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2697
_reflns_number_gt                1910
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0670P)²+0.1397P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2697
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1330
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
C14 C 0.88897(17) 0.4940(2) 0.14731(6) 0.0271(3) Uani 1 1 d . . . . .
O3 O 0.72698(14) 0.7802(2) 0.10345(6) 0.0456(3) Uani 1 1 d . . . . .
H3 H 0.630325 0.815467 0.089376 0.055 Uiso 1 1 calc R U . . .
O2 O 0.59815(14) 0.4584(2) 0.11529(6) 0.0484(3) Uani 1 1 d . . . . .
C13 C 1.03730(18) 0.6223(3) 0.14841(6) 0.0294(3) Uani 1 1 d . . . . .
H13 H 1.035205 0.764607 0.131607 0.035 Uiso 1 1 calc R U . . .
C16 C 1.04473(19) 0.2071(3) 0.19839(6) 0.0323(3) Uani 1 1 d . . . . .
H16 H 1.046498 0.065546 0.215641 0.039 Uiso 1 1 calc R U . . .
C11 C 1.19329(19) 0.3343(3) 0.19983(6) 0.0316(3) Uani 1 1 d . . . . .
C12 C 1.18797(18) 0.5414(3) 0.17411(7) 0.0328(4) Uani 1 1 d . . . . .
H12 H 1.288794 0.628514 0.174154 0.039 Uiso 1 1 calc R U . . .
C18 C 0.72376(18) 0.5738(3) 0.12041(6) 0.0306(3) Uani 1 1 d . . . . .
C15 C 0.89467(19) 0.2849(3) 0.17210(6) 0.0312(3) Uani 1 1 d . . . . .
H15 H 0.795036 0.195520 0.170916 0.037 Uiso 1 1 calc R U . . .
C17 C 1.3557(2) 0.2496(3) 0.22935(8) 0.0460(4) Uani 1 1 d . . . . .
H17A H 1.454079 0.287806 0.205725 0.069 Uiso 1 1 calc R U . . .
H17B H 1.348790 0.090032 0.233297 0.069 Uiso 1 1 calc R U . . .
H17C H 1.369668 0.316179 0.268176 0.069 Uiso 1 1 calc R U . . .
N1 N 0.41572(15) 0.8859(2) 0.06039(6) 0.0356(3) Uani 1 1 d . . . . .
C3 C 0.08724(17) 0.9766(2) 0.01246(6) 0.0269(3) Uani 1 1 d . . . . .
C2 C 0.17577(19) 1.1268(3) 0.04775(7) 0.0349(4) Uani 1 1 d . . . . .
H2 H 0.124938 1.263815 0.056562 0.042 Uiso 1 1 calc R U . . .
C4 C 0.1697(2) 0.7782(3) 0.00238(7) 0.0374(4) Uani 1 1 d . . . . .
H4 H 0.116040 0.669695 -0.021648 0.045 Uiso 1 1 calc R U . . .
C1 C 0.3380(2) 1.0766(3) 0.07005(7) 0.0381(4) Uani 1 1 d . . . . .
H1 H 0.396621 1.183142 0.093341 0.046 Uiso 1 1 calc R U . . .
C5 C 0.3299(2) 0.7402(3) 0.02754(7) 0.0415(4) Uani 1 1 d . . . . .
H5 H 0.382034 0.602046 0.021045 0.050 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
C14 C15 1.397(2) . ?
C14 C13 1.3974(19) . ?
C14 C18 1.494(2) . ?
O3 C18 1.3186(19) . ?
O2 C18 1.2102(18) . ?
C13 C12 1.390(2) . ?
C16 C15 1.385(2) . ?
C16 C11 1.395(2) . ?
C11 C12 1.394(2) . ?
C11 C17 1.510(2) . ?
N1 C5 1.332(2) . ?
N1 C1 1.334(2) . ?
C3 C2 1.392(2) . ?
C3 C4 1.394(2) . ?
C3 C3 1.489(3) 3_575 ?
C2 C1 1.386(2) . ?
C4 C5 1.381(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 C14 C13 119.19(13) . . ?
C15 C14 C18 118.79(13) . . ?
C13 C14 C18 122.02(13) . . ?
C12 C13 C14 119.96(14) . . ?
C15 C16 C11 120.77(14) . . ?
C12 C11 C16 118.67(14) . . ?
C12 C11 C17 120.87(14) . . ?
C16 C11 C17 120.46(15) . . ?
C13 C12 C11 120.99(14) . . ?
O2 C18 O3 123.35(14) . . ?
O2 C18 C14 122.53(15) . . ?
O3 C18 C14 114.11(13) . . ?
C16 C15 C14 120.40(13) . . ?
C5 N1 C1 116.87(13) . . ?
C2 C3 C4 116.37(13) . . ?
C2 C3 C3 121.95(17) . 3_575 ?
C4 C3 C3 121.67(17) . 3_575 ?
C1 C2 C3 120.08(15) . . ?
C5 C4 C3 119.58(15) . . ?
N1 C1 C2 123.18(15) . . ?
N1 C5 C4 123.89(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 C14 C13 C12 -0.2(2) . . . . ?
C18 C14 C13 C12 179.78(13) . . . . ?
C15 C16 C11 C12 -0.2(2) . . . . ?
C15 C16 C11 C17 179.11(15) . . . . ?
C14 C13 C12 C11 -1.0(2) . . . . ?
C16 C11 C12 C13 1.2(2) . . . . ?
C17 C11 C12 C13 -178.11(15) . . . . ?
C15 C14 C18 O2 -5.7(2) . . . . ?
C13 C14 C18 O2 174.32(14) . . . . ?
C15 C14 C18 O3 173.64(13) . . . . ?
C13 C14 C18 O3 -6.3(2) . . . . ?
C11 C16 C15 C14 -1.0(2) . . . . ?
C13 C14 C15 C16 1.2(2) . . . . ?
C18 C14 C15 C16 -178.79(13) . . . . ?
C4 C3 C2 C1 1.0(2) . . . . ?
C3 C3 C2 C1 179.99(16) 3_575 . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C3 C4 C5 -178.49(17) 3_575 . . . ?
C5 N1 C1 C2 0.0(2) . . . . ?
C3 C2 C1 N1 -1.3(2) . . . . ?
C1 N1 C5 C4 1.6(2) . . . . ?
C3 C4 C5 N1 -1.9(3) . . . . ?

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
O3 H3 N1 0.84 1.84 2.6748(17) 178.0 .
C1 H1 O2_$1 0.95 2.35 3.241(2) 156.9 1_565

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.223
_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_BIPYracPBA
_database_code_depnum_ccdc_archive 'CCDC 1912006'
loop_
_audit_author_name
_audit_author_address
'Nikoletta Bathori'
;Cape Peninsula University of Technology
South Africa
;
_audit_update_record             
;
2019-12-29 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          80.5-84.0
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N O2'
_chemical_formula_weight         242.29

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                   5.6951(11)
_cell_length_b                   32.968(7)
_cell_length_c                   7.2241(14)
_cell_angle_alpha                90
_cell_angle_beta                 109.74(3)
_cell_angle_gamma                90
_cell_volume                     1276.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    10554
_cell_measurement_theta_min      2.471
_cell_measurement_theta_max      28.255

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.992
_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      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Duo Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10554
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.471
_diffrn_reflns_theta_max         28.255
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3116
_reflns_number_gt                2470
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0358P)²+1.0060P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3116
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1378
_refine_ls_wR_factor_gt          0.1316
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
O3 O 0.8775(3) 0.09990(5) 0.1813(2) 0.0418(4) Uani 1 1 d . . . . .
H3 H 0.874463 0.081803 0.098659 0.050 Uiso 1 1 calc R U . . .
N1 N 0.9001(3) 0.05304(5) -0.1047(2) 0.0336(4) Uani 1 1 d . . . . .
O2 O 0.5478(3) 0.06647(5) 0.2003(2) 0.0451(4) Uani 1 1 d . . . . .
C6 C 0.5718(4) 0.16688(6) 0.2433(3) 0.0314(4) Uani 1 1 d . . . . .
C3 C 0.9784(3) 0.01103(5) -0.4172(3) 0.0270(4) Uani 1 1 d . . . . .
C5 C 0.7743(4) 0.01922(6) -0.1781(3) 0.0330(4) Uani 1 1 d . . . . .
H5 H 0.655509 0.009586 -0.122585 0.040 Uiso 1 1 calc R U . . .
C15 C 0.6876(4) 0.09500(6) 0.2432(3) 0.0306(4) Uani 1 1 d . . . . .
C2 C 1.1091(4) 0.04640(6) -0.3399(3) 0.0347(4) Uani 1 1 d . . . . .
H2 H 1.227546 0.056995 -0.393343 0.042 Uiso 1 1 calc R U . . .
C4 C 0.8080(4) -0.00254(6) -0.3311(3) 0.0306(4) Uani 1 1 d . . . . .
H4 H 0.715209 -0.026646 -0.377135 0.037 Uiso 1 1 calc R U . . .
C7 C 0.3223(4) 0.17052(6) 0.1268(3) 0.0354(5) Uani 1 1 d . . . . .
H7 H 0.205844 0.150501 0.134339 0.043 Uiso 1 1 calc R U . . .
C12 C 0.6708(4) 0.13014(6) 0.3766(3) 0.0320(4) Uani 1 1 d . . . . .
H12 H 0.843513 0.136596 0.465913 0.038 Uiso 1 1 calc R U . . .
C1 C 1.0659(4) 0.06598(6) -0.1855(3) 0.0370(5) Uani 1 1 d . . . . .
H1 H 1.158635 0.089830 -0.134173 0.044 Uiso 1 1 calc R U . . .
C10 C 0.6550(5) 0.22910(6) 0.1012(3) 0.0420(5) Uani 1 1 d . . . . .
H10 H 0.770761 0.249247 0.093723 0.050 Uiso 1 1 calc R U . . .
C13 C 0.5149(4) 0.11877(6) 0.5034(3) 0.0387(5) Uani 1 1 d . . . . .
H13B H 0.339008 0.115296 0.417922 0.046 Uiso 1 1 calc R U . . .
H13A H 0.574197 0.092443 0.568339 0.046 Uiso 1 1 calc R U . . .
C8 C 0.2415(4) 0.20323(7) -0.0009(3) 0.0397(5) Uani 1 1 d . . . . .
H8 H 0.070350 0.205499 -0.078894 0.048 Uiso 1 1 calc R U . . .
C11 C 0.7368(4) 0.19665(6) 0.2293(3) 0.0369(5) Uani 1 1 d . . . . .
H11 H 0.907876 0.194832 0.308289 0.044 Uiso 1 1 calc R U . . .
C9 C 0.4091(5) 0.23246(6) -0.0148(3) 0.0414(5) Uani 1 1 d . . . . .
H9 H 0.354679 0.254556 -0.103451 0.050 Uiso 1 1 calc R U . . .
C14 C 0.5272(6) 0.15019(8) 0.6590(4) 0.0562(7) Uani 1 1 d . . . . .
H14A H 0.699827 0.152921 0.747784 0.084 Uiso 1 1 calc R U . . .
H14B H 0.421136 0.141680 0.734233 0.084 Uiso 1 1 calc R U . . .
H14C H 0.468446 0.176342 0.595770 0.084 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
O3 C15 1.312(2) . ?
N1 C5 1.335(3) . ?
N1 C1 1.337(3) . ?
O2 C15 1.203(2) . ?
C6 C11 1.386(3) . ?
C6 C7 1.391(3) . ?
C6 C12 1.532(3) . ?
C3 C4 1.392(2) . ?
C3 C2 1.395(3) . ?
C3 C3 1.489(4) 3_754 ?
C5 C4 1.384(3) . ?
C15 C12 1.531(3) . ?
C2 C1 1.381(3) . ?
C7 C8 1.392(3) . ?
C12 C13 1.523(3) . ?
C10 C9 1.372(3) . ?
C10 C11 1.388(3) . ?
C13 C14 1.513(3) . ?
C8 C9 1.384(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 117.18(17) . . ?
C11 C6 C7 118.31(19) . . ?
C11 C6 C12 119.41(19) . . ?
C7 C6 C12 122.20(18) . . ?
C4 C3 C2 116.62(17) . . ?
C4 C3 C3 122.1(2) . 3_754 ?
C2 C3 C3 121.3(2) . 3_754 ?
N1 C5 C4 123.33(18) . . ?
O2 C15 O3 123.95(18) . . ?
O2 C15 C12 125.23(18) . . ?
O3 C15 C12 110.82(16) . . ?
C1 C2 C3 119.87(18) . . ?
C5 C4 C3 119.74(18) . . ?
C6 C7 C8 120.59(19) . . ?
C13 C12 C15 111.46(16) . . ?
C13 C12 C6 114.03(16) . . ?
C15 C12 C6 106.90(15) . . ?
N1 C1 C2 123.25(19) . . ?
C9 C10 C11 120.9(2) . . ?
C14 C13 C12 112.86(18) . . ?
C9 C8 C7 120.4(2) . . ?
C6 C11 C10 120.7(2) . . ?
C10 C9 C8 119.1(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
C1 N1 C5 C4 0.1(3) . . . . ?
C4 C3 C2 C1 0.1(3) . . . . ?
C3 C3 C2 C1 -179.6(2) 3_754 . . . ?
N1 C5 C4 C3 -0.8(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C3 C4 C5 -179.7(2) 3_754 . . . ?
C11 C6 C7 C8 0.2(3) . . . . ?
C12 C6 C7 C8 -176.37(17) . . . . ?
O2 C15 C12 C13 19.1(3) . . . . ?
O3 C15 C12 C13 -160.61(18) . . . . ?
O2 C15 C12 C6 -106.2(2) . . . . ?
O3 C15 C12 C6 74.2(2) . . . . ?
C11 C6 C12 C13 135.34(19) . . . . ?
C7 C6 C12 C13 -48.1(3) . . . . ?
C11 C6 C12 C15 -101.0(2) . . . . ?
C7 C6 C12 C15 75.5(2) . . . . ?
C5 N1 C1 C2 0.7(3) . . . . ?
C3 C2 C1 N1 -0.8(3) . . . . ?
C15 C12 C13 C14 171.05(19) . . . . ?
C6 C12 C13 C14 -67.8(3) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C7 C6 C11 C10 -0.4(3) . . . . ?
C12 C6 C11 C10 176.25(18) . . . . ?
C9 C10 C11 C6 -0.1(3) . . . . ?
C11 C10 C9 C8 0.8(3) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?

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
O3 H3 N1 0.84 1.80 2.618(2) 165.6 .
C4 H4 O2_$1 0.95 2.63 3.276(2) 126.1 3_655
C5 H5 O2_$1 0.95 2.74 3.342(3) 122.1 3_655
C5 H5 O2 0.95 3.21 3.735(3) 116.7 .

_refine_diff_density_max         0.490
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.044


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_ETBIPY-SPSA
_database_code_depnum_ccdc_archive 'CCDC 1912009'
loop_
_audit_author_name
_audit_author_address
'Nikoletta Bathori'
;Cape Peninsula University of Technology
South Africa
;
_audit_update_record             
;
2019-04-24 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41

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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   6.5705(13)
_cell_length_b                   9.2493(18)
_cell_length_c                   17.129(3)
_cell_angle_alpha                92.82(3)
_cell_angle_beta                 99.52(3)
_cell_angle_gamma                110.25(3)
_cell_volume                     956.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    16309
_cell_measurement_theta_min      1.213
_cell_measurement_theta_max      28.294

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.991
_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      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Duo Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16309
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.213
_diffrn_reflns_theta_max         28.294
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             9350
_reflns_number_gt                8032
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.981
_reflns_Friedel_fraction_max     0.972
_reflns_Friedel_fraction_full    0.976

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0487P)²+0.0319P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3420 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration rm
_refine_ls_number_reflns         9350
_refine_ls_number_parameters     509
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
N1A N 1.5295(3) 1.4392(2) 0.14393(12) 0.0241(4) Uani 1 1 d . . . . .
C1A C 1.5799(4) 1.4051(3) 0.21793(15) 0.0257(5) Uani 1 1 d . . . . .
H1A H 1.646865 1.487718 0.259899 0.031 Uiso 1 1 calc R U . . .
N2A N 1.0556(3) 0.3737(2) 0.19865(13) 0.0248(4) Uani 1 1 d . . . . .
C2A C 1.5387(4) 1.2552(3) 0.23591(14) 0.0252(5) Uani 1 1 d . . . . .
H2A H 1.577422 1.236302 0.289346 0.030 Uiso 1 1 calc R U . . .
C3A C 1.4405(4) 1.1313(3) 0.17581(14) 0.0222(5) Uani 1 1 d . . . . .
C4A C 1.3867(4) 1.1675(3) 0.09926(15) 0.0271(5) Uani 1 1 d . . . . .
H4A H 1.317544 1.087226 0.056254 0.033 Uiso 1 1 calc R U . . .
C5A C 1.4343(4) 1.3209(3) 0.08592(15) 0.0270(5) Uani 1 1 d . . . . .
H5A H 1.397605 1.343302 0.033041 0.032 Uiso 1 1 calc R U . . .
C6A C 1.4036(4) 0.9677(3) 0.19545(15) 0.0240(5) Uani 1 1 d . . . . .
H6A H 1.396283 0.964071 0.252623 0.029 Uiso 1 1 calc R U . . .
H6B H 1.532429 0.941174 0.186891 0.029 Uiso 1 1 calc R U . . .
C7A C 1.1948(4) 0.8458(3) 0.14659(15) 0.0248(5) Uani 1 1 d . . . . .
H7A H 1.066489 0.873614 0.154502 0.030 Uiso 1 1 calc R U . . .
H7B H 1.203374 0.848774 0.089496 0.030 Uiso 1 1 calc R U . . .
C8A C 1.1537(4) 0.6824(3) 0.16621(14) 0.0218(5) Uani 1 1 d . . . . .
C9A C 1.2103(4) 0.6456(3) 0.24259(14) 0.0251(5) Uani 1 1 d . . . . .
H9A H 1.283857 0.725677 0.285429 0.030 Uiso 1 1 calc R U . . .
C10A C 1.1589(4) 0.4918(3) 0.25587(15) 0.0273(5) Uani 1 1 d . . . . .
H10A H 1.199280 0.469226 0.308440 0.033 Uiso 1 1 calc R U . . .
C11A C 1.0028(4) 0.4078(3) 0.12459(15) 0.0253(5) Uani 1 1 d . . . . .
H11A H 0.931152 0.325067 0.082917 0.030 Uiso 1 1 calc R U . . .
C12A C 1.0482(4) 0.5582(3) 0.10639(15) 0.0248(5) Uani 1 1 d . . . . .
H12A H 1.007531 0.577079 0.053098 0.030 Uiso 1 1 calc R U . . .
N1B N 2.0724(4) 0.7402(3) 0.75150(14) 0.0351(5) Uani 1 1 d . . . . .
C1B C 2.0911(6) 0.7324(4) 0.67479(18) 0.0479(8) Uani 1 1 d . . . . .
H1B H 2.019688 0.784096 0.639557 0.058 Uiso 1 1 calc R U . . .
N2B N 1.6723(4) 0.0687(3) 0.59075(13) 0.0351(5) Uani 1 1 d . . . . .
C2B C 2.2091(6) 0.6530(4) 0.64480(17) 0.0443(7) Uani 1 1 d . . . . .
H2B H 2.216441 0.650032 0.589844 0.053 Uiso 1 1 calc R U . . .
C3B C 2.3173(4) 0.5772(3) 0.69451(15) 0.0319(6) Uani 1 1 d . . . . .
C4B C 2.2998(4) 0.5878(3) 0.77409(15) 0.0325(6) Uani 1 1 d . . . . .
H4B H 2.371835 0.539096 0.810945 0.039 Uiso 1 1 calc R U . . .
C5B C 2.1780(4) 0.6688(3) 0.79950(16) 0.0315(5) Uani 1 1 d . . . . .
H5B H 2.168556 0.674230 0.854248 0.038 Uiso 1 1 calc R U . . .
C6B C 2.4483(5) 0.4894(4) 0.66398(18) 0.0411(7) Uani 1 1 d . . . . .
H6D H 2.605508 0.539931 0.690393 0.049 Uiso 1 1 calc R U . . .
H6C H 2.439510 0.496362 0.606099 0.049 Uiso 1 1 calc R U . . .
C7B C 2.3698(5) 0.3176(4) 0.67783(18) 0.0410(7) Uani 1 1 d . . . . .
H7C H 2.453969 0.266406 0.651273 0.049 Uiso 1 1 calc R U . . .
H7D H 2.404418 0.310609 0.735697 0.049 Uiso 1 1 calc R U . . .
C8B C 2.1263(5) 0.2305(3) 0.64758(16) 0.0328(6) Uani 1 1 d . . . . .
C9B C 1.9872(5) 0.1556(4) 0.69719(17) 0.0441(7) Uani 1 1 d . . . . .
H9B H 2.044808 0.158912 0.752186 0.053 Uiso 1 1 calc R U . . .
C10B C 1.7656(5) 0.0761(4) 0.66722(17) 0.0460(7) Uani 1 1 d . . . . .
H10B H 1.674639 0.024135 0.702496 0.055 Uiso 1 1 calc R U . . .
C11B C 1.8064(4) 0.1414(3) 0.54268(15) 0.0314(5) Uani 1 1 d . . . . .
H11B H 1.744115 0.137873 0.488145 0.038 Uiso 1 1 calc R U . . .
C12B C 2.0300(5) 0.2212(3) 0.56802(16) 0.0338(6) Uani 1 1 d . . . . .
H12B H 2.118039 0.269796 0.531209 0.041 Uiso 1 1 calc R U . . .
O1C O 0.9713(3) 0.09141(19) 0.23446(10) 0.0294(4) Uani 1 1 d . . . . .
H1C H 0.998137 0.184794 0.227122 0.035 Uiso 1 1 calc R U . . .
O2C O 1.0368(3) 0.1857(2) 0.36283(11) 0.0387(5) Uani 1 1 d . . . . .
O3C O 1.2476(3) -0.0439(2) 0.52747(11) 0.0388(5) Uani 1 1 d . . . . .
H3C H 1.384437 -0.017438 0.544168 0.047 Uiso 1 1 calc R U . . .
O4C O 1.3463(3) -0.0383(2) 0.40879(11) 0.0373(4) Uani 1 1 d . . . . .
C11C C 0.8376(4) -0.2776(3) 0.42877(14) 0.0242(5) Uani 1 1 d . . . . .
C12C C 0.6240(4) -0.3207(3) 0.44338(15) 0.0301(5) Uani 1 1 d . . . . .
H12C H 0.559336 -0.244433 0.449112 0.036 Uiso 1 1 calc R U . . .
C13C C 0.5045(4) -0.4750(3) 0.44965(16) 0.0332(6) Uani 1 1 d . . . . .
H13C H 0.357880 -0.503849 0.459030 0.040 Uiso 1 1 calc R U . . .
C14C C 0.5979(5) -0.5864(3) 0.44229(16) 0.0340(6) Uani 1 1 d . . . . .
H14C H 0.515564 -0.691768 0.446567 0.041 Uiso 1 1 calc R U . . .
C15C C 0.8110(4) -0.5448(3) 0.42873(16) 0.0313(6) Uani 1 1 d . . . . .
H15C H 0.875926 -0.621215 0.424099 0.038 Uiso 1 1 calc R U . . .
C16C C 0.9308(4) -0.3901(3) 0.42185(14) 0.0268(5) Uani 1 1 d . . . . .
H16C H 1.077225 -0.361640 0.412344 0.032 Uiso 1 1 calc R U . . .
C17C C 0.9593(4) -0.1101(3) 0.41484(15) 0.0251(5) Uani 1 1 d . . . . .
H17C H 0.899691 -0.042200 0.443926 0.030 Uiso 1 1 calc R U . . .
C18C C 1.2055(4) -0.0595(3) 0.44889(14) 0.0261(5) Uani 1 1 d . . . . .
C19C C 0.9147(4) -0.0902(3) 0.32717(15) 0.0272(5) Uani 1 1 d . . . . .
H19C H 0.754647 -0.142765 0.305412 0.033 Uiso 1 1 calc R U . . .
H19D H 0.994869 -0.141931 0.298698 0.033 Uiso 1 1 calc R U . . .
C20C C 0.9838(4) 0.0779(3) 0.31084(15) 0.0257(5) Uani 1 1 d . . . . .
O1D O 1.6395(3) 0.72228(19) 1.10750(10) 0.0297(4) Uani 1 1 d . . . . .
H1D H 1.588009 0.628358 1.114744 0.036 Uiso 1 1 calc R U . . .
O2D O 1.5217(3) 0.6260(2) 0.97865(11) 0.0382(5) Uani 1 1 d . . . . .
O3D O 1.8111(3) 0.8514(2) 0.81479(11) 0.0384(5) Uani 1 1 d . . . . .
H3D H 1.897652 0.813573 0.798375 0.046 Uiso 1 1 calc R U . . .
O4D O 2.0091(3) 0.8502(2) 0.93391(12) 0.0389(5) Uani 1 1 d . . . . .
C11D C 1.7215(4) 1.0901(3) 0.91263(14) 0.0234(5) Uani 1 1 d . . . . .
C12D C 1.9322(4) 1.2011(3) 0.91976(14) 0.0267(5) Uani 1 1 d . . . . .
H12D H 2.057443 1.170691 0.929365 0.032 Uiso 1 1 calc R U . . .
C13D C 1.9619(5) 1.3565(3) 0.91298(16) 0.0322(6) Uani 1 1 d . . . . .
H13D H 2.106510 1.431181 0.917435 0.039 Uiso 1 1 calc R U . . .
C14D C 1.7809(5) 1.4012(3) 0.89980(16) 0.0327(6) Uani 1 1 d . . . . .
H14D H 1.800396 1.506975 0.895660 0.039 Uiso 1 1 calc R U . . .
C15D C 1.5709(5) 1.2916(3) 0.89262(16) 0.0339(6) Uani 1 1 d . . . . .
H15D H 1.446293 1.322643 0.883394 0.041 Uiso 1 1 calc R U . . .
C16D C 1.5401(4) 1.1366(3) 0.89875(15) 0.0305(5) Uani 1 1 d . . . . .
H16D H 1.394943 1.062200 0.893449 0.037 Uiso 1 1 calc R U . . .
C17D C 1.6870(4) 0.9230(3) 0.92627(15) 0.0244(5) Uani 1 1 d . . . . .
H17D H 1.536125 0.856700 0.896460 0.029 Uiso 1 1 calc R U . . .
C18D C 1.8536(4) 0.8703(3) 0.89316(14) 0.0257(5) Uani 1 1 d . . . . .
C19D C 1.6939(4) 0.9026(3) 1.01447(15) 0.0260(5) Uani 1 1 d . . . . .
H19F H 1.848390 0.953273 1.043728 0.031 Uiso 1 1 calc R U . . .
H19E H 1.604044 0.956344 1.035427 0.031 Uiso 1 1 calc R U . . .
C20D C 1.6094(4) 0.7346(3) 1.03098(15) 0.0250(5) Uani 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
N1A C1A 1.338(3) . ?
N1A C5A 1.338(3) . ?
C1A C2A 1.379(3) . ?
N2A C10A 1.333(3) . ?
N2A C11A 1.341(3) . ?
C2A C3A 1.393(3) . ?
C3A C4A 1.388(3) . ?
C3A C6A 1.512(3) . ?
C4A C5A 1.382(3) . ?
C6A C7A 1.520(3) . ?
C7A C8A 1.506(3) . ?
C8A C9A 1.392(3) . ?
C8A C12A 1.396(3) . ?
C9A C10A 1.383(3) . ?
C11A C12A 1.381(3) . ?
N1B C5B 1.332(4) . ?
N1B C1B 1.340(4) . ?
C1B C2B 1.376(4) . ?
N2B C11B 1.338(4) . ?
N2B C10B 1.339(4) . ?
C2B C3B 1.388(4) . ?
C3B C4B 1.388(3) . ?
C3B C6B 1.505(4) . ?
C4B C5B 1.375(4) . ?
C6B C7B 1.536(4) . ?
C7B C8B 1.507(4) . ?
C8B C9B 1.383(4) . ?
C8B C12B 1.390(4) . ?
C9B C10B 1.378(4) . ?
C11B C12B 1.378(4) . ?
O1C C20C 1.312(3) . ?
O2C C20C 1.216(3) . ?
O3C C18C 1.319(3) . ?
O4C C18C 1.210(3) . ?
C11C C16C 1.387(3) . ?
C11C C12C 1.389(3) . ?
C11C C17C 1.529(3) . ?
C12C C13C 1.390(4) . ?
C13C C14C 1.381(4) . ?
C14C C15C 1.380(4) . ?
C15C C16C 1.396(3) . ?
C17C C19C 1.514(3) . ?
C17C C18C 1.521(3) . ?
C19C C20C 1.516(3) . ?
O1D C20D 1.309(3) . ?
O2D C20D 1.218(3) . ?
O3D C18D 1.315(3) . ?
O4D C18D 1.214(3) . ?
C11D C16D 1.390(3) . ?
C11D C12D 1.390(3) . ?
C11D C17D 1.519(3) . ?
C12D C13D 1.396(3) . ?
C13D C14D 1.377(4) . ?
C14D C15D 1.382(4) . ?
C15D C16D 1.389(4) . ?
C17D C18D 1.518(4) . ?
C17D C19D 1.527(3) . ?
C19D C20D 1.517(3) . ?

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
C1A N1A C5A 117.5(2) . . ?
N1A C1A C2A 122.8(2) . . ?
C10A N2A C11A 117.5(2) . . ?
C1A C2A C3A 120.1(2) . . ?
C4A C3A C2A 116.8(2) . . ?
C4A C3A C6A 123.4(2) . . ?
C2A C3A C6A 119.8(2) . . ?
C5A C4A C3A 119.7(2) . . ?
N1A C5A C4A 123.1(2) . . ?
C3A C6A C7A 114.26(18) . . ?
C8A C7A C6A 114.97(18) . . ?
C9A C8A C12A 116.6(2) . . ?
C9A C8A C7A 123.5(2) . . ?
C12A C8A C7A 119.8(2) . . ?
C10A C9A C8A 119.7(2) . . ?
N2A C10A C9A 123.3(2) . . ?
N2A C11A C12A 122.8(2) . . ?
C11A C12A C8A 120.1(2) . . ?
C5B N1B C1B 116.9(2) . . ?
N1B C1B C2B 122.9(3) . . ?
C11B N2B C10B 116.7(3) . . ?
C1B C2B C3B 120.3(3) . . ?
C2B C3B C4B 116.4(3) . . ?
C2B C3B C6B 121.8(2) . . ?
C4B C3B C6B 121.8(3) . . ?
C5B C4B C3B 119.9(3) . . ?
N1B C5B C4B 123.6(2) . . ?
C3B C6B C7B 114.0(2) . . ?
C8B C7B C6B 114.2(2) . . ?
C9B C8B C12B 116.6(3) . . ?
C9B C8B C7B 122.0(3) . . ?
C12B C8B C7B 121.5(3) . . ?
C10B C9B C8B 120.3(3) . . ?
N2B C10B C9B 123.1(3) . . ?
N2B C11B C12B 123.5(2) . . ?
C11B C12B C8B 119.8(3) . . ?
C16C C11C C12C 119.1(2) . . ?
C16C C11C C17C 121.2(2) . . ?
C12C C11C C17C 119.6(2) . . ?
C11C C12C C13C 120.3(2) . . ?
C14C C13C C12C 120.3(2) . . ?
C15C C14C C13C 120.0(2) . . ?
C14C C15C C16C 119.8(2) . . ?
C11C C16C C15C 120.5(2) . . ?
C19C C17C C18C 111.9(2) . . ?
C19C C17C C11C 110.7(2) . . ?
C18C C17C C11C 110.9(2) . . ?
O4C C18C O3C 123.8(2) . . ?
O4C C18C C17C 124.1(2) . . ?
O3C C18C C17C 112.0(2) . . ?
C17C C19C C20C 113.6(2) . . ?
O2C C20C O1C 124.8(2) . . ?
O2C C20C C19C 123.2(2) . . ?
O1C C20C C19C 111.9(2) . . ?
C16D C11D C12D 118.9(2) . . ?
C16D C11D C17D 119.5(2) . . ?
C12D C11D C17D 121.4(2) . . ?
C11D C12D C13D 120.7(2) . . ?
C14D C13D C12D 119.8(2) . . ?
C13D C14D C15D 119.8(2) . . ?
C14D C15D C16D 120.7(3) . . ?
C15D C16D C11D 120.1(2) . . ?
C18D C17D C11D 110.81(19) . . ?
C18D C17D C19D 112.2(2) . . ?
C11D C17D C19D 110.6(2) . . ?
O4D C18D O3D 124.0(2) . . ?
O4D C18D C17D 124.2(2) . . ?
O3D C18D C17D 111.7(2) . . ?
C20D C19D C17D 113.9(2) . . ?
O2D C20D O1D 125.0(2) . . ?
O2D C20D C19D 123.3(2) . . ?
O1D C20D C19D 111.7(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
C5A N1A C1A C2A 0.3(3) . . . . ?
N1A C1A C2A C3A -0.1(4) . . . . ?
C1A C2A C3A C4A -0.5(3) . . . . ?
C1A C2A C3A C6A 177.8(2) . . . . ?
C2A C3A C4A C5A 0.9(4) . . . . ?
C6A C3A C4A C5A -177.4(2) . . . . ?
C1A N1A C5A C4A 0.0(4) . . . . ?
C3A C4A C5A N1A -0.7(4) . . . . ?
C4A C3A C6A C7A -36.1(3) . . . . ?
C2A C3A C6A C7A 145.7(2) . . . . ?
C3A C6A C7A C8A -179.1(2) . . . . ?
C6A C7A C8A C9A 34.1(3) . . . . ?
C6A C7A C8A C12A -147.7(2) . . . . ?
C12A C8A C9A C10A -0.7(3) . . . . ?
C7A C8A C9A C10A 177.6(2) . . . . ?
C11A N2A C10A C9A 1.0(3) . . . . ?
C8A C9A C10A N2A -0.1(4) . . . . ?
C10A N2A C11A C12A -1.0(3) . . . . ?
N2A C11A C12A C8A 0.1(4) . . . . ?
C9A C8A C12A C11A 0.7(3) . . . . ?
C7A C8A C12A C11A -177.6(2) . . . . ?
C5B N1B C1B C2B 1.2(5) . . . . ?
N1B C1B C2B C3B -0.6(5) . . . . ?
C1B C2B C3B C4B -0.4(4) . . . . ?
C1B C2B C3B C6B -179.9(3) . . . . ?
C2B C3B C4B C5B 0.7(4) . . . . ?
C6B C3B C4B C5B -179.8(2) . . . . ?
C1B N1B C5B C4B -0.9(4) . . . . ?
C3B C4B C5B N1B 0.0(4) . . . . ?
C2B C3B C6B C7B -122.0(3) . . . . ?
C4B C3B C6B C7B 58.5(3) . . . . ?
C3B C6B C7B C8B 52.7(3) . . . . ?
C6B C7B C8B C9B -122.0(3) . . . . ?
C6B C7B C8B C12B 58.1(3) . . . . ?
C12B C8B C9B C10B 0.4(4) . . . . ?
C7B C8B C9B C10B -179.5(3) . . . . ?
C11B N2B C10B C9B 1.0(4) . . . . ?
C8B C9B C10B N2B -1.2(5) . . . . ?
C10B N2B C11B C12B 0.0(4) . . . . ?
N2B C11B C12B C8B -0.8(4) . . . . ?
C9B C8B C12B C11B 0.5(4) . . . . ?
C7B C8B C12B C11B -179.5(2) . . . . ?
C16C C11C C12C C13C -1.0(4) . . . . ?
C17C C11C C12C C13C 174.7(2) . . . . ?
C11C C12C C13C C14C 0.7(4) . . . . ?
C12C C13C C14C C15C 0.1(4) . . . . ?
C13C C14C C15C C16C -0.5(4) . . . . ?
C12C C11C C16C C15C 0.6(4) . . . . ?
C17C C11C C16C C15C -175.1(2) . . . . ?
C14C C15C C16C C11C 0.2(4) . . . . ?
C16C C11C C17C C19C 86.0(3) . . . . ?
C12C C11C C17C C19C -89.7(3) . . . . ?
C16C C11C C17C C18C -38.9(3) . . . . ?
C12C C11C C17C C18C 145.5(2) . . . . ?
C19C C17C C18C O4C -15.1(3) . . . . ?
C11C C17C C18C O4C 109.1(3) . . . . ?
C19C C17C C18C O3C 166.0(2) . . . . ?
C11C C17C C18C O3C -69.8(3) . . . . ?
C18C C17C C19C C20C -69.4(3) . . . . ?
C11C C17C C19C C20C 166.4(2) . . . . ?
C17C C19C C20C O2C -11.0(4) . . . . ?
C17C C19C C20C O1C 171.3(2) . . . . ?
C16D C11D C12D C13D -0.1(4) . . . . ?
C17D C11D C12D C13D -175.1(2) . . . . ?
C11D C12D C13D C14D 0.6(4) . . . . ?
C12D C13D C14D C15D -0.6(4) . . . . ?
C13D C14D C15D C16D 0.2(4) . . . . ?
C14D C15D C16D C11D 0.3(4) . . . . ?
C12D C11D C16D C15D -0.3(4) . . . . ?
C17D C11D C16D C15D 174.8(2) . . . . ?
C16D C11D C17D C18D 146.8(2) . . . . ?
C12D C11D C17D C18D -38.3(3) . . . . ?
C16D C11D C17D C19D -88.2(3) . . . . ?
C12D C11D C17D C19D 86.8(3) . . . . ?
C11D C17D C18D O4D 107.3(3) . . . . ?
C19D C17D C18D O4D -16.8(3) . . . . ?
C11D C17D C18D O3D -71.7(3) . . . . ?
C19D C17D C18D O3D 164.2(2) . . . . ?
C18D C17D C19D C20D -69.1(3) . . . . ?
C11D C17D C19D C20D 166.7(2) . . . . ?
C17D C19D C20D O2D -7.6(4) . . . . ?
C17D C19D C20D O1D 173.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1C H1C N2A 0.84 1.77 2.601(3) 172.5 .
C10A H10A O2C 0.95 2.74 3.382(3) 125.4 .
O3C H3C N2B 0.84 1.80 2.631(3) 169.3 .
C11B H11B O4C 0.95 2.64 3.319(4) 128.4 .
O3D H3D N1B 0.84 1.79 2.628(3) 172.8 .
C5B H5B O4D 0.95 2.65 3.331(3) 128.7 .
O1D H1D N1A_$1 0.84 1.77 2.601(3) 168.6 1_546
C5A H5A O2D_$2 0.95 2.72 3.377(3) 127.2 1_564

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_ETBIPYracPSA
_database_code_depnum_ccdc_archive 'CCDC 1912008'
loop_
_audit_author_name
_audit_author_address
'Nikoletta Bathori'
;Cape Peninsula University of Technology
South Africa
;
_audit_update_record             
;
2019-04-24 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.5593(13)
_cell_length_b                   9.2837(19)
_cell_length_c                   16.826(3)
_cell_angle_alpha                82.39(3)
_cell_angle_beta                 81.52(3)
_cell_angle_gamma                69.63(3)
_cell_volume                     946.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4116
_cell_measurement_theta_min      2.349
_cell_measurement_theta_max      27.331

_exptl_crystal_description       chunk
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.992
_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      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Duo Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4116
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.349
_diffrn_reflns_theta_max         27.331
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             4116
_reflns_number_gt                2860
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0349P)²+2.5587P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4116
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0777
_refine_ls_wR_factor_ref         0.1803
_refine_ls_wR_factor_gt          0.1634
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.6058(5) -0.0413(3) 0.36089(14) 0.0424(7) Uani 1 1 d . . . . .
H1 H 0.688443 -0.005425 0.379475 0.051 Uiso 1 1 calc R U . . .
O2 O 0.8345(4) -0.0420(3) 0.24817(15) 0.0378(6) Uani 1 1 d . . . . .
O3 O 0.4489(4) 0.1613(2) 0.05888(13) 0.0289(5) Uani 1 1 d . . . . .
H3 H 0.393362 0.257615 0.051214 0.035 Uiso 1 1 calc R U . . .
O4 O 0.3460(5) 0.2056(3) 0.18932(15) 0.0422(7) Uani 1 1 d . . . . .
C7 C 0.5560(5) -0.2803(4) 0.25832(17) 0.0238(6) Uani 1 1 d . . . . .
C8 C 0.3793(6) -0.3354(4) 0.26984(19) 0.0298(7) Uani 1 1 d . . . . .
H8 H 0.233666 -0.264958 0.271764 0.036 Uiso 1 1 calc R U . . .
C9 C 0.4176(7) -0.4940(4) 0.2785(2) 0.0371(9) Uani 1 1 d . . . . .
H9 H 0.297268 -0.530809 0.286342 0.045 Uiso 1 1 calc R U . . .
C10 C 0.6272(7) -0.5976(4) 0.2758(2) 0.0371(9) Uani 1 1 d . . . . .
H10 H 0.651614 -0.705323 0.281452 0.044 Uiso 1 1 calc R U . . .
C11 C 0.8037(6) -0.5436(4) 0.2646(2) 0.0347(8) Uani 1 1 d . . . . .
H11 H 0.948958 -0.614565 0.262782 0.042 Uiso 1 1 calc R U . . .
C12 C 0.7672(5) -0.3869(4) 0.25624(19) 0.0285(7) Uani 1 1 d . . . . .
H12 H 0.888442 -0.351133 0.248919 0.034 Uiso 1 1 calc R U . . .
C13 C 0.5101(5) -0.1066(4) 0.24403(18) 0.0257(7) Uani 1 1 d . . . . .
H13 H 0.359003 -0.053739 0.269619 0.031 Uiso 1 1 calc R U . . .
C14 C 0.6693(5) -0.0592(4) 0.28323(19) 0.0275(7) Uani 1 1 d . . . . .
C15 C 0.5175(5) -0.0558(4) 0.15354(19) 0.0267(7) Uani 1 1 d . . . . .
H15A H 0.670760 -0.094331 0.128502 0.032 Uiso 1 1 calc R U . . .
H15B H 0.431127 -0.102610 0.128354 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4275(5) 0.1190(4) 0.1367(2) 0.0270(7) Uani 1 1 d . . . . .
N1A N 0.2763(4) 0.4577(3) 0.02319(16) 0.0238(6) Uani 1 1 d . . . . .
C1A C 0.2468(5) 0.5226(4) -0.05257(19) 0.0261(7) Uani 1 1 d . . . . .
H1A H 0.293167 0.458306 -0.095856 0.031 Uiso 1 1 calc R U . . .
C2A C 0.1513(5) 0.6798(4) -0.06928(18) 0.0239(6) Uani 1 1 d . . . . .
H2A H 0.130509 0.721463 -0.123345 0.029 Uiso 1 1 calc R U . . .
C3A C 0.0854(5) 0.7774(3) -0.00761(18) 0.0216(6) Uani 1 1 d . . . . .
C4A C 0.1201(5) 0.7090(4) 0.07039(18) 0.0257(7) Uani 1 1 d . . . . .
H4A H 0.079006 0.770845 0.114636 0.031 Uiso 1 1 calc R U . . .
C5A C 0.2148(5) 0.5505(4) 0.08296(19) 0.0271(7) Uani 1 1 d . . . . .
H5A H 0.237009 0.505763 0.136487 0.032 Uiso 1 1 calc R U . . .
C6A C -0.0265(5) 0.9493(3) -0.02630(18) 0.0236(6) Uani 1 1 d . . . . .
H6A H -0.186768 0.971508 -0.019546 0.028 Uiso 1 1 calc R U . . .
H6B H 0.016559 0.977559 -0.083513 0.028 Uiso 1 1 calc R U . . .
N1B N 0.8104(5) 0.1028(3) 0.42635(16) 0.0335(7) Uani 1 1 d . . . . .
C1B C 1.0008(6) 0.1193(4) 0.3949(2) 0.0386(9) Uani 1 1 d . . . . .
H1B H 1.081213 0.061020 0.351281 0.046 Uiso 1 1 calc R U . . .
C2B C 1.0865(7) 0.2166(4) 0.4227(3) 0.0436(9) Uani 1 1 d . . . . .
H2B H 1.224495 0.222499 0.399143 0.052 Uiso 1 1 calc R U . . .
C3B C 0.9714(7) 0.3063(4) 0.4852(2) 0.0396(9) Uani 1 1 d . . . . .
C4B C 0.7736(7) 0.2879(4) 0.5179(2) 0.0443(10) Uani 1 1 d . . . . .
H4B H 0.688919 0.345700 0.561137 0.053 Uiso 1 1 calc R U . . .
C5B C 0.7003(7) 0.1862(4) 0.4877(2) 0.0374(8) Uani 1 1 d . . . . .
H5B H 0.565580 0.174767 0.511515 0.045 Uiso 1 1 calc R U . . .
C6B C 1.0553(8) 0.4182(4) 0.5162(3) 0.0540(12) Uani 1 1 d . . . . .
H6C H 1.030156 0.410904 0.575900 0.065 Uiso 1 1 calc R U . . .
H6D H 1.214966 0.389452 0.500519 0.065 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 C14 1.326(4) . ?
O2 C14 1.206(4) . ?
O3 C16 1.318(4) . ?
O4 C16 1.211(4) . ?
C7 C12 1.393(5) . ?
C7 C8 1.401(4) . ?
C7 C13 1.526(4) . ?
C8 C9 1.396(5) . ?
C9 C10 1.375(6) . ?
C10 C11 1.393(5) . ?
C11 C12 1.381(5) . ?
C13 C14 1.523(5) . ?
C13 C15 1.532(4) . ?
C15 C16 1.524(4) . ?
N1A C5A 1.336(4) . ?
N1A C1A 1.347(4) . ?
C1A C2A 1.382(4) . ?
C2A C3A 1.389(4) . ?
C3A C4A 1.394(4) . ?
C3A C6A 1.518(4) . ?
C4A C5A 1.384(4) . ?
C6A C6A 1.527(6) 2_575 ?
N1B C1B 1.335(5) . ?
N1B C5B 1.338(4) . ?
C1B C2B 1.376(5) . ?
C2B C3B 1.388(5) . ?
C3B C4B 1.390(6) . ?
C3B C6B 1.512(5) . ?
C4B C5B 1.377(5) . ?
C6B C6B 1.504(8) 2_766 ?

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
C12 C7 C8 118.5(3) . . ?
C12 C7 C13 122.7(3) . . ?
C8 C7 C13 118.8(3) . . ?
C9 C8 C7 119.9(3) . . ?
C10 C9 C8 120.9(3) . . ?
C9 C10 C11 119.6(3) . . ?
C12 C11 C10 119.9(3) . . ?
C11 C12 C7 121.3(3) . . ?
C14 C13 C7 111.1(3) . . ?
C14 C13 C15 111.2(3) . . ?
C7 C13 C15 110.4(2) . . ?
O2 C14 O1 124.1(3) . . ?
O2 C14 C13 124.1(3) . . ?
O1 C14 C13 111.8(3) . . ?
C16 C15 C13 112.2(3) . . ?
O4 C16 O3 125.4(3) . . ?
O4 C16 C15 123.1(3) . . ?
O3 C16 C15 111.5(3) . . ?
C5A N1A C1A 118.0(3) . . ?
N1A C1A C2A 122.0(3) . . ?
C1A C2A C3A 120.5(3) . . ?
C2A C3A C4A 116.9(3) . . ?
C2A C3A C6A 120.0(3) . . ?
C4A C3A C6A 123.0(3) . . ?
C5A C4A C3A 119.6(3) . . ?
N1A C5A C4A 122.9(3) . . ?
C3A C6A C6A 114.4(3) . 2_575 ?
C1B N1B C5B 117.2(3) . . ?
N1B C1B C2B 123.2(3) . . ?
C1B C2B C3B 120.0(4) . . ?
C2B C3B C4B 116.5(3) . . ?
C2B C3B C6B 122.1(4) . . ?
C4B C3B C6B 121.5(4) . . ?
C5B C4B C3B 120.1(4) . . ?
N1B C5B C4B 122.9(4) . . ?
C6B C6B C3B 112.0(4) 2_766 . ?

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
C12 C7 C8 C9 -0.3(5) . . . . ?
C13 C7 C8 C9 176.4(3) . . . . ?
C7 C8 C9 C10 -0.1(5) . . . . ?
C8 C9 C10 C11 0.3(5) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C10 C11 C12 C7 -0.3(5) . . . . ?
C8 C7 C12 C11 0.5(5) . . . . ?
C13 C7 C12 C11 -176.1(3) . . . . ?
C12 C7 C13 C14 -39.1(4) . . . . ?
C8 C7 C13 C14 144.3(3) . . . . ?
C12 C7 C13 C15 84.8(4) . . . . ?
C8 C7 C13 C15 -91.8(3) . . . . ?
C7 C13 C14 O2 96.1(4) . . . . ?
C15 C13 C14 O2 -27.4(4) . . . . ?
C7 C13 C14 O1 -83.1(3) . . . . ?
C15 C13 C14 O1 153.5(3) . . . . ?
C14 C13 C15 C16 -67.9(3) . . . . ?
C7 C13 C15 C16 168.2(3) . . . . ?
C13 C15 C16 O4 -4.8(5) . . . . ?
C13 C15 C16 O3 175.7(3) . . . . ?
C5A N1A C1A C2A -1.6(5) . . . . ?
N1A C1A C2A C3A 1.2(5) . . . . ?
C1A C2A C3A C4A -0.1(4) . . . . ?
C1A C2A C3A C6A -177.9(3) . . . . ?
C2A C3A C4A C5A -0.5(5) . . . . ?
C6A C3A C4A C5A 177.1(3) . . . . ?
C1A N1A C5A C4A 0.9(5) . . . . ?
C3A C4A C5A N1A 0.1(5) . . . . ?
C2A C3A C6A C6A -145.9(3) . . . 2_575 ?
C4A C3A C6A C6A 36.6(5) . . . 2_575 ?
C5B N1B C1B C2B 0.1(5) . . . . ?
N1B C1B C2B C3B -1.5(6) . . . . ?
C1B C2B C3B C4B 1.7(6) . . . . ?
C1B C2B C3B C6B -178.2(4) . . . . ?
C2B C3B C4B C5B -0.6(6) . . . . ?
C6B C3B C4B C5B 179.3(4) . . . . ?
C1B N1B C5B C4B 1.1(5) . . . . ?
C3B C4B C5B N1B -0.8(6) . . . . ?
C2B C3B C6B C6B 101.0(6) . . . 2_766 ?
C4B C3B C6B C6B -79.0(7) . . . 2_766 ?

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
O1 H1 N1B 0.84 1.80 2.622(4) 167.5 .
O3 H3 N1A 0.84 1.77 2.609(3) 173.4 .
C5A H5A O4 0.95 2.69 3.349(4) 127.4 .
C1B H1B O2 0.95 2.98 3.527(4) 117.9 .

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_BIPYracPSA
_database_code_depnum_ccdc_archive 'CCDC 1912007'
loop_
_audit_author_name
_audit_author_address
'Nikoletta Bathori'
;Cape Peninsula University of Technology
South Africa
;
_audit_update_record             
;
2019-04-24 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N2 O4'
_chemical_formula_weight         350.36

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.3729(19)
_cell_length_b                   18.545(4)
_cell_length_c                   11.135(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.89(3)
_cell_angle_gamma                90
_cell_volume                     1769.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    12630
_cell_measurement_theta_min      2.196
_cell_measurement_theta_max      28.366

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Duo Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12630
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.196
_diffrn_reflns_theta_max         28.366
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4388
_reflns_number_gt                3351
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0533P)²+0.2954P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4388
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1115
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.26419(10) 0.41244(5) 0.41880(9) 0.0371(2) Uani 1 1 d . . . . .
O2 O 0.06922(10) 0.43374(6) 0.22513(9) 0.0380(2) Uani 1 1 d . . . . .
H22 H 0.130808 0.465099 0.219338 0.046 Uiso 1 1 calc R U . . .
O3 O 0.38734(11) 0.21252(6) 0.51655(9) 0.0414(3) Uani 1 1 d . . . . .
H3 H 0.456721 0.194810 0.495813 0.050 Uiso 1 1 calc R U . . .
N1 N 0.60924(13) 0.15162(7) 0.45991(12) 0.0374(3) Uani 1 1 d . . . . .
C17 C 0.04902(13) 0.32907(6) 0.33896(11) 0.0257(3) Uani 1 1 d . . . . .
H17 H 0.013831 0.303841 0.252368 0.031 Uiso 1 1 calc R U . . .
O4 O 0.28726(12) 0.24791(6) 0.30790(9) 0.0433(3) Uani 1 1 d . . . . .
N2 N 1.23319(12) 0.02503(6) 0.31111(11) 0.0340(3) Uani 1 1 d . . . . .
C18 C 0.13994(13) 0.39570(7) 0.33321(11) 0.0259(3) Uani 1 1 d . . . . .
C3 C 0.85667(14) 0.10340(7) 0.40063(12) 0.0276(3) Uani 1 1 d . . . . .
C6 C 0.98839(14) 0.07786(7) 0.36953(12) 0.0267(3) Uani 1 1 d . . . . .
C11 C -0.09452(13) 0.34792(7) 0.36369(12) 0.0265(3) Uani 1 1 d . . . . .
C7 C 1.13700(15) 0.06849(7) 0.46638(12) 0.0322(3) Uani 1 1 d . . . . .
H7 H 1.158118 0.079722 0.555210 0.039 Uiso 1 1 calc R U . . .
C12 C -0.22588(15) 0.30401(7) 0.31169(13) 0.0334(3) Uani 1 1 d . . . . .
H12 H -0.228036 0.265377 0.254953 0.040 Uiso 1 1 calc R U . . .
C19 C 0.15352(14) 0.27760(7) 0.44517(12) 0.0282(3) Uani 1 1 d . . . . .
H19A H 0.200006 0.303951 0.529560 0.034 Uiso 1 1 calc R U . . .
H19B H 0.088685 0.238111 0.456074 0.034 Uiso 1 1 calc R U . . .
C20 C 0.28293(14) 0.24541(7) 0.41459(12) 0.0283(3) Uani 1 1 d . . . . .
C8 C 1.25464(15) 0.04265(8) 0.43289(13) 0.0348(3) Uani 1 1 d . . . . .
H8 H 1.356111 0.037228 0.500620 0.042 Uiso 1 1 calc R U . . .
C2 C 0.88175(16) 0.13473(8) 0.52054(13) 0.0347(3) Uani 1 1 d . . . . .
H2 H 0.985093 0.140510 0.585093 0.042 Uiso 1 1 calc R U . . .
C4 C 0.70253(15) 0.09711(8) 0.31110(14) 0.0383(3) Uani 1 1 d . . . . .
H4 H 0.678716 0.075722 0.227659 0.046 Uiso 1 1 calc R U . . .
C16 C -0.09540(16) 0.40441(8) 0.44444(15) 0.0391(3) Uani 1 1 d . . . . .
H16 H -0.007104 0.435214 0.479945 0.047 Uiso 1 1 calc R U . . .
C13 C -0.35405(15) 0.31610(8) 0.34195(15) 0.0411(3) Uani 1 1 d . . . . .
H13 H -0.442792 0.285569 0.306445 0.049 Uiso 1 1 calc R U . . .
C5 C 0.58352(16) 0.12215(9) 0.34380(15) 0.0417(3) Uani 1 1 d . . . . .
H5 H 0.478966 0.118112 0.280624 0.050 Uiso 1 1 calc R U . . .
C9 C 1.09127(17) 0.03565(10) 0.21789(14) 0.0460(4) Uani 1 1 d . . . . .
H9 H 1.073963 0.024408 0.129829 0.055 Uiso 1 1 calc R U . . .
C1 C 0.75649(16) 0.15757(8) 0.54632(14) 0.0386(3) Uani 1 1 d . . . . .
H1 H 0.776594 0.178463 0.629519 0.046 Uiso 1 1 calc R U . . .
C10 C 0.96778(17) 0.06206(10) 0.24190(14) 0.0451(4) Uani 1 1 d . . . . .
H10 H 0.869125 0.069392 0.171334 0.054 Uiso 1 1 calc R U . . .
C14 C -0.35241(18) 0.37211(9) 0.42304(17) 0.0503(4) Uani 1 1 d . . . . .
H14 H -0.439846 0.380201 0.443918 0.060 Uiso 1 1 calc R U . . .
C15 C -0.2235(2) 0.41680(9) 0.47440(19) 0.0540(4) Uani 1 1 d . . . . .
H15 H -0.222557 0.455822 0.529981 0.065 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 C18 1.2092(15) . ?
O2 C18 1.3190(15) . ?
O3 C20 1.3111(15) . ?
N1 C1 1.3295(18) . ?
N1 C5 1.3328(18) . ?
C17 C18 1.5169(17) . ?
C17 C11 1.5192(16) . ?
C17 C19 1.5268(17) . ?
O4 C20 1.2060(15) . ?
N2 C8 1.3287(17) . ?
N2 C9 1.3294(18) . ?
C3 C2 1.3862(17) . ?
C3 C4 1.3886(19) . ?
C3 C6 1.4883(17) . ?
C6 C7 1.3845(18) . ?
C6 C10 1.3859(18) . ?
C11 C16 1.3828(19) . ?
C11 C12 1.3918(18) . ?
C7 C8 1.3847(18) . ?
C12 C13 1.3909(19) . ?
C19 C20 1.5094(16) . ?
C2 C1 1.3832(18) . ?
C4 C5 1.3861(19) . ?
C16 C15 1.389(2) . ?
C13 C14 1.372(2) . ?
C9 C10 1.3791(19) . ?
C14 C15 1.384(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 117.59(11) . . ?
C18 C17 C11 111.97(10) . . ?
C18 C17 C19 110.29(10) . . ?
C11 C17 C19 109.93(9) . . ?
C8 N2 C9 116.78(11) . . ?
O1 C18 O2 123.34(12) . . ?
O1 C18 C17 123.65(11) . . ?
O2 C18 C17 113.01(10) . . ?
C2 C3 C4 116.62(12) . . ?
C2 C3 C6 121.63(11) . . ?
C4 C3 C6 121.74(11) . . ?
C7 C6 C10 116.79(12) . . ?
C7 C6 C3 121.76(11) . . ?
C10 C6 C3 121.44(11) . . ?
C16 C11 C12 118.47(12) . . ?
C16 C11 C17 122.08(11) . . ?
C12 C11 C17 119.28(11) . . ?
C6 C7 C8 119.56(12) . . ?
C13 C12 C11 120.67(13) . . ?
C20 C19 C17 113.24(10) . . ?
O4 C20 O3 124.05(12) . . ?
O4 C20 C19 123.90(12) . . ?
O3 C20 C19 112.02(10) . . ?
N2 C8 C7 123.51(12) . . ?
C1 C2 C3 120.08(13) . . ?
C5 C4 C3 119.82(13) . . ?
C11 C16 C15 120.98(13) . . ?
C14 C13 C12 120.06(13) . . ?
N1 C5 C4 122.93(13) . . ?
N2 C9 C10 123.66(13) . . ?
N1 C1 C2 122.96(13) . . ?
C9 C10 C6 119.64(13) . . ?
C13 C14 C15 120.03(14) . . ?
C14 C15 C16 119.78(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C17 C18 O1 107.47(14) . . . . ?
C19 C17 C18 O1 -15.28(17) . . . . ?
C11 C17 C18 O2 -72.37(13) . . . . ?
C19 C17 C18 O2 164.88(10) . . . . ?
C2 C3 C6 C7 15.2(2) . . . . ?
C4 C3 C6 C7 -164.83(13) . . . . ?
C2 C3 C6 C10 -165.00(14) . . . . ?
C4 C3 C6 C10 15.0(2) . . . . ?
C18 C17 C11 C16 -35.85(16) . . . . ?
C19 C17 C11 C16 87.11(15) . . . . ?
C18 C17 C11 C12 149.02(11) . . . . ?
C19 C17 C11 C12 -88.02(14) . . . . ?
C10 C6 C7 C8 -1.6(2) . . . . ?
C3 C6 C7 C8 178.17(12) . . . . ?
C16 C11 C12 C13 -0.95(19) . . . . ?
C17 C11 C12 C13 174.36(12) . . . . ?
C18 C17 C19 C20 -66.71(13) . . . . ?
C11 C17 C19 C20 169.35(10) . . . . ?
C17 C19 C20 O4 -13.90(18) . . . . ?
C17 C19 C20 O3 168.09(11) . . . . ?
C9 N2 C8 C7 2.3(2) . . . . ?
C6 C7 C8 N2 -0.8(2) . . . . ?
C4 C3 C2 C1 0.3(2) . . . . ?
C6 C3 C2 C1 -179.72(13) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C6 C3 C4 C5 -179.49(13) . . . . ?
C12 C11 C16 C15 0.7(2) . . . . ?
C17 C11 C16 C15 -174.48(14) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C1 N1 C5 C4 0.8(2) . . . . ?
C3 C4 C5 N1 -1.1(2) . . . . ?
C8 N2 C9 C10 -1.4(2) . . . . ?
C5 N1 C1 C2 0.0(2) . . . . ?
C3 C2 C1 N1 -0.6(2) . . . . ?
N2 C9 C10 C6 -1.1(3) . . . . ?
C7 C6 C10 C9 2.5(2) . . . . ?
C3 C6 C10 C9 -177.28(14) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C11 C16 C15 C14 0.0(3) . . . . ?

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
O3 H3 N1 0.84 1.82 2.6573(14) 175.9 .
O2 H22 N2_$1 0.84 1.82 2.6578(15) 171.9 2_655
C10 H10 O1_$2 0.95 2.60 3.354(2) 136.8 4_665
C1 H1 O4_$3 0.95 2.38 3.3105(18) 166.7 4_666
C17 H17 O3_$4 1.00 2.42 3.3727(18) 158.3 4_565
C8 H8 O2_$5 0.95 2.55 3.421(2) 153.1 4_766

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.036

