# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_cu_fa0732_kotora
_database_code_depnum_ccdc_archive 'CCDC 2352747'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2024-05-02 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 O2'
_chemical_formula_sum            'C18 H14 O2'
_chemical_formula_weight         262.29
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 '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                   10.3866(9)
_cell_length_b                   5.6440(5)
_cell_length_c                   12.0776(10)
_cell_angle_alpha                90
_cell_angle_beta                 114.196(5)
_cell_angle_gamma                90
_cell_volume                     645.81(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5064
_cell_measurement_theta_min      4.0127
_cell_measurement_theta_max      68.2832

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.574
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.036
_exptl_absorpt_coefficient_mu    0.692
_shelx_estimated_absorpt_T_min   0.692
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9349
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.013
_diffrn_reflns_theta_max         68.410
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2357
_reflns_number_gt                2148
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.998

_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 Instrument Service v8.5.1.2 Release'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0785P)²+0.1060P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 851 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2357
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1243
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 0.5443(3) 0.2753(7) 0.7224(3) 0.0335(8) Uani 1 1 d . . . . .
C2 C 0.6661(3) 0.2521(6) 0.6782(3) 0.0314(7) Uani 1 1 d . . . . .
H2 H 0.636899 0.310075 0.586782 0.038 Uiso 1 1 d R U . . .
C3 C 0.5971(4) 0.0385(7) 0.7015(3) 0.0398(8) Uani 1 1 d . . . . .
H31 H 0.531804 -0.059443 0.629515 0.048 Uiso 1 1 d R U . . .
H32 H 0.654404 -0.067343 0.780615 0.048 Uiso 1 1 d R U . . .
O1 O 0.5739(2) 0.7105(5) 0.9553(2) 0.0402(6) Uani 1 1 d . . . . .
O2 O 0.3664(2) 0.2672(5) 0.5224(2) 0.0442(7) Uani 1 1 d . . . . .
C4 C 0.5756(3) 0.3527(7) 0.8510(3) 0.0348(8) Uani 1 1 d . . . . .
H4A H 0.537158 0.232006 0.888682 0.042 Uiso 1 1 calc R U . . .
H4B H 0.679287 0.355862 0.897687 0.042 Uiso 1 1 calc R U . . .
C5 C 0.5172(3) 0.5910(6) 0.8631(3) 0.0322(7) Uani 1 1 d . . . . .
C6 C 0.3859(3) 0.6756(7) 0.7611(3) 0.0340(8) Uani 1 1 d . . . . .
C7 C 0.3356(3) 0.5611(7) 0.6479(3) 0.0344(8) Uani 1 1 d . . . . .
C8 C 0.4106(3) 0.3579(7) 0.6232(3) 0.0359(8) Uani 1 1 d . . . . .
C9 C 0.3157(4) 0.8738(7) 0.7777(3) 0.0375(8) Uani 1 1 d . . . . .
H9 H 0.348583 0.948320 0.854951 0.045 Uiso 1 1 calc R U . . .
C10 C 0.1978(4) 0.9630(8) 0.6819(3) 0.0422(9) Uani 1 1 d . . . . .
H10 H 0.151379 1.100204 0.692901 0.051 Uiso 1 1 calc R U . . .
C11 C 0.1481(4) 0.8494(8) 0.5693(3) 0.0438(9) Uani 1 1 d . . . . .
H11 H 0.067098 0.909365 0.503840 0.053 Uiso 1 1 calc R U . . .
C12 C 0.2149(3) 0.6526(8) 0.5524(3) 0.0415(9) Uani 1 1 d . . . . .
H12 H 0.179521 0.576881 0.475358 0.050 Uiso 1 1 calc R U . . .
C13 C 0.8163(3) 0.3170(6) 0.7565(3) 0.0296(7) Uani 1 1 d . . . . .
C14 C 0.8691(3) 0.5280(6) 0.7338(3) 0.0336(8) Uani 1 1 d . . . . .
H14 H 0.808018 0.633293 0.673900 0.040 Uiso 1 1 calc R U . . .
C15 C 1.0100(3) 0.5874(7) 0.7973(3) 0.0386(8) Uani 1 1 d . . . . .
H15 H 1.044723 0.733384 0.781408 0.046 Uiso 1 1 calc R U . . .
C16 C 1.1007(3) 0.4325(7) 0.8845(3) 0.0379(8) Uani 1 1 d . . . . .
H16 H 1.197938 0.470003 0.926474 0.045 Uiso 1 1 calc R U . . .
C17 C 1.0486(4) 0.2275(7) 0.9090(3) 0.0434(9) Uani 1 1 d . . . . .
H17 H 1.109468 0.124075 0.970083 0.052 Uiso 1 1 calc R U . . .
C18 C 0.9067(4) 0.1672(7) 0.8454(3) 0.0398(8) Uani 1 1 d . . . . .
H18 H 0.872014 0.022899 0.863026 0.048 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
C1 C8 1.489(5) . ?
C1 C3 1.505(5) . ?
C1 C4 1.515(4) . ?
C1 C2 1.567(5) . ?
C2 C3 1.487(5) . ?
C2 C13 1.501(4) . ?
C2 H2 1.0698 . ?
C3 H31 1.0192 . ?
C3 H32 1.0760 . ?
O1 C5 1.227(4) . ?
O2 C8 1.224(4) . ?
C4 C5 1.507(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.492(5) . ?
C6 C9 1.395(5) . ?
C6 C7 1.405(5) . ?
C7 C12 1.408(5) . ?
C7 C8 1.484(5) . ?
C9 C10 1.389(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.397(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.369(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.385(5) . ?
C13 C18 1.387(5) . ?
C14 C15 1.386(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.360(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.396(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C1 C3 115.3(3) . . ?
C8 C1 C4 118.2(3) . . ?
C3 C1 C4 119.2(3) . . ?
C8 C1 C2 111.6(3) . . ?
C3 C1 C2 57.9(2) . . ?
C4 C1 C2 120.6(3) . . ?
C3 C2 C13 122.4(3) . . ?
C3 C2 C1 59.0(2) . . ?
C13 C2 C1 122.7(3) . . ?
C3 C2 H2 119.2 . . ?
C13 C2 H2 110.9 . . ?
C1 C2 H2 113.5 . . ?
C2 C3 C1 63.2(2) . . ?
C2 C3 H31 118.8 . . ?
C1 C3 H31 117.6 . . ?
C2 C3 H32 119.0 . . ?
C1 C3 H32 116.8 . . ?
H31 C3 H32 112.9 . . ?
C5 C4 C1 115.5(3) . . ?
C5 C4 H4A 108.4 . . ?
C1 C4 H4A 108.4 . . ?
C5 C4 H4B 108.4 . . ?
C1 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
O1 C5 C6 120.6(3) . . ?
O1 C5 C4 121.1(3) . . ?
C6 C5 C4 118.3(3) . . ?
C9 C6 C7 120.1(3) . . ?
C9 C6 C5 119.5(3) . . ?
C7 C6 C5 120.4(3) . . ?
C6 C7 C12 118.7(4) . . ?
C6 C7 C8 122.3(3) . . ?
C12 C7 C8 118.9(3) . . ?
O2 C8 C7 120.6(3) . . ?
O2 C8 C1 121.1(3) . . ?
C7 C8 C1 118.3(3) . . ?
C10 C9 C6 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C6 C9 H9 119.8 . . ?
C9 C10 C11 119.5(4) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C14 C13 C18 118.7(3) . . ?
C14 C13 C2 118.6(3) . . ?
C18 C13 C2 122.6(3) . . ?
C13 C14 C15 120.8(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C16 119.9(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 120.3(3) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.056



####################################################################### 
# 
# 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_mo_fa0779_kotora_5
_database_code_depnum_ccdc_archive 'CCDC 2352749'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2024-05-02 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 Br O2'
_chemical_formula_sum            'C18 H13 Br O2'
_chemical_formula_weight         341.19
_chemical_compound_source        'synthesized by the authors'

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'
Br Br -0.2901 2.4595 '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                   8.2511(6)
_cell_length_b                   11.6841(9)
_cell_length_c                   15.8119(14)
_cell_angle_alpha                94.173(3)
_cell_angle_beta                 96.426(3)
_cell_angle_gamma                109.320(2)
_cell_volume                     1419.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9588
_cell_measurement_theta_min      2.3939
_cell_measurement_theta_max      28.2857

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    2.897
_shelx_estimated_absorpt_T_min   0.465
_shelx_estimated_absorpt_T_max   0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_process_details   
;
Sevvana, M., Ruf, M., Usón, I., Sheldrick, G. M., and Herbst-Irmer, R. (2019)
"Non-merohedral twinning: from minerals to proteins"
Acta. Cryst. D75, 1040-1050.
doi:10.1107/S2059798319010179
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11973
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.860
_diffrn_reflns_theta_max         28.301
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             11973
_reflns_number_gt                11269
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker Instrument Service v8.5.1.2 Release'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component 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)+(0.0329P)²+1.5637P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11973
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_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
Br1A Br 0.59716(3) 0.79550(3) 0.09913(2) 0.02345(7) Uani 1 1 d . . . . .
O1A O 0.7065(2) 0.50072(19) 0.11540(13) 0.0230(4) Uani 1 1 d . . . . .
O2A O 0.1750(2) 0.54179(19) 0.26880(13) 0.0216(4) Uani 1 1 d . . . . .
C1A C 0.2767(3) 0.4947(2) 0.14044(16) 0.0129(4) Uani 1 1 d . . . . .
C2A C 0.2377(3) 0.5874(2) 0.08231(16) 0.0140(5) Uani 1 1 d . . . . .
H2A H 0.295379 0.597497 0.030547 0.017 Uiso 1 1 d R U . . .
C3A C 0.1008(3) 0.4686(2) 0.08915(18) 0.0174(5) Uani 1 1 d . . . . .
H31A H 0.074459 0.416560 0.045095 0.021 Uiso 1 1 d R U . . .
H32A H -0.001242 0.448759 0.109695 0.021 Uiso 1 1 d R U . . .
C4A C 0.3997(3) 0.4337(2) 0.11055(16) 0.0143(5) Uani 1 1 d . . . . .
H4AA H 0.359663 0.347562 0.122582 0.017 Uiso 1 1 calc R U . . .
H4AB H 0.395920 0.433816 0.047750 0.017 Uiso 1 1 calc R U . . .
C5A C 0.5839(3) 0.4954(2) 0.15300(17) 0.0142(5) Uani 1 1 d . . . . .
C6A C 0.6089(3) 0.5436(2) 0.24542(17) 0.0140(5) Uani 1 1 d . . . . .
C7A C 0.4670(3) 0.5488(2) 0.28495(16) 0.0141(5) Uani 1 1 d . . . . .
C8A C 0.2934(3) 0.5272(2) 0.23416(16) 0.0143(5) Uani 1 1 d . . . . .
C9A C 0.7734(3) 0.5789(2) 0.29304(18) 0.0200(5) Uani 1 1 d . . . . .
H9A H 0.870002 0.577254 0.266070 0.024 Uiso 1 1 calc R U . . .
C10A C 0.7958(4) 0.6167(3) 0.3802(2) 0.0238(6) Uani 1 1 d . . . . .
H10A H 0.908617 0.642595 0.412496 0.029 Uiso 1 1 calc R U . . .
C11A C 0.6542(4) 0.6170(3) 0.42094(18) 0.0236(6) Uani 1 1 d . . . . .
H11A H 0.669570 0.639937 0.480965 0.028 Uiso 1 1 calc R U . . .
C12A C 0.4913(4) 0.5834(3) 0.37302(18) 0.0203(5) Uani 1 1 d . . . . .
H12A H 0.394803 0.584027 0.400453 0.024 Uiso 1 1 calc R U . . .
C13A C 0.2363(3) 0.7079(2) 0.11748(15) 0.0133(5) Uani 1 1 d . . . . .
C14A C 0.3858(3) 0.8110(2) 0.12668(16) 0.0147(5) Uani 1 1 d . . . . .
C15A C 0.3885(3) 0.9263(2) 0.15550(17) 0.0184(5) Uani 1 1 d . . . . .
H15A H 0.492585 0.994568 0.160829 0.022 Uiso 1 1 calc R U . . .
C16A C 0.2377(4) 0.9409(2) 0.17649(17) 0.0196(5) Uani 1 1 d . . . . .
H16A H 0.237772 1.019672 0.196261 0.023 Uiso 1 1 calc R U . . .
C17A C 0.0870(4) 0.8411(3) 0.16873(17) 0.0189(5) Uani 1 1 d . . . . .
H17A H -0.016166 0.851366 0.183615 0.023 Uiso 1 1 calc R U . . .
C18A C 0.0855(3) 0.7257(2) 0.13925(16) 0.0156(5) Uani 1 1 d . . . . .
H18A H -0.019206 0.657817 0.133776 0.019 Uiso 1 1 calc R U . . .
Br1B Br 0.70764(4) -0.06167(3) 0.33198(2) 0.02392(7) Uani 1 1 d . . . . .
O1B O 1.1508(3) 0.2656(2) 0.36787(14) 0.0274(5) Uani 1 1 d . . . . .
O2B O 0.5227(2) 0.22940(17) 0.20598(13) 0.0194(4) Uani 1 1 d . . . . .
C1B C 0.7132(3) 0.2680(2) 0.33664(17) 0.0148(5) Uani 1 1 d . . . . .
C2B C 0.5965(3) 0.1643(2) 0.38253(17) 0.0167(5) Uani 1 1 d . . . . .
H2B H 0.510531 0.106333 0.342054 0.020 Uiso 1 1 d R U . . .
C3B C 0.5790(3) 0.2876(3) 0.38769(18) 0.0194(5) Uani 1 1 d . . . . .
H31B H 0.477323 0.301545 0.358269 0.023 Uiso 1 1 d R U . . .
H32B H 0.628523 0.336645 0.442568 0.023 Uiso 1 1 d R U . . .
C4B C 0.9030(3) 0.3272(2) 0.37188(17) 0.0163(5) Uani 1 1 d . . . . .
H4BA H 0.918912 0.320816 0.434138 0.020 Uiso 1 1 calc R U . . .
H4BB H 0.939861 0.415001 0.364219 0.020 Uiso 1 1 calc R U . . .
C5B C 1.0182(3) 0.2707(2) 0.32958(17) 0.0156(5) Uani 1 1 d . . . . .
C6B C 0.9642(3) 0.2268(2) 0.23602(16) 0.0134(5) Uani 1 1 d . . . . .
C7B C 0.8013(3) 0.2195(2) 0.19384(16) 0.0135(5) Uani 1 1 d . . . . .
C8B C 0.6670(3) 0.2422(2) 0.24219(17) 0.0140(5) Uani 1 1 d . . . . .
C9B C 1.0799(3) 0.1943(2) 0.19033(18) 0.0177(5) Uani 1 1 d . . . . .
H9B H 1.190779 0.200451 0.218577 0.021 Uiso 1 1 calc R U . . .
C10B C 1.0338(4) 0.1528(2) 0.10353(19) 0.0203(5) Uani 1 1 d . . . . .
H10B H 1.112387 0.129252 0.072718 0.024 Uiso 1 1 calc R U . . .
C11B C 0.8723(4) 0.1456(2) 0.06158(18) 0.0204(5) Uani 1 1 d . . . . .
H11B H 0.840858 0.116869 0.002236 0.025 Uiso 1 1 calc R U . . .
C12B C 0.7575(3) 0.1802(2) 0.10621(17) 0.0171(5) Uani 1 1 d . . . . .
H12B H 0.648807 0.177233 0.077071 0.021 Uiso 1 1 calc R U . . .
C13B C 0.6735(3) 0.1174(2) 0.45592(18) 0.0181(5) Uani 1 1 d . . . . .
C14B C 0.7272(3) 0.0167(3) 0.44426(17) 0.0184(5) Uani 1 1 d . . . . .
C15B C 0.7941(4) -0.0306(3) 0.51233(19) 0.0230(6) Uani 1 1 d . . . . .
H15B H 0.826550 -0.100713 0.502506 0.028 Uiso 1 1 calc R U . . .
C16B C 0.8129(4) 0.0254(3) 0.5947(2) 0.0258(6) Uani 1 1 d . . . . .
H16B H 0.859870 -0.005650 0.641657 0.031 Uiso 1 1 calc R U . . .
C17B C 0.7635(4) 0.1268(3) 0.60891(19) 0.0261(6) Uani 1 1 d . . . . .
H17B H 0.777830 0.165975 0.665395 0.031 Uiso 1 1 calc R U . . .
C18B C 0.6926(4) 0.1707(3) 0.53965(19) 0.0236(6) Uani 1 1 d . . . . .
H18B H 0.656345 0.238943 0.549919 0.028 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
Br1A C14A 1.906(3) . ?
O1A C5A 1.216(3) . ?
O2A C8A 1.224(3) . ?
C1A C8A 1.482(4) . ?
C1A C3A 1.505(3) . ?
C1A C4A 1.517(3) . ?
C1A C2A 1.559(3) . ?
C2A C13A 1.481(3) . ?
C2A C3A 1.491(3) . ?
C2A H2A 0.9873 . ?
C3A H31A 0.8483 . ?
C3A H32A 0.9007 . ?
C4A C5A 1.502(3) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C5A C6A 1.494(4) . ?
C6A C9A 1.391(4) . ?
C6A C7A 1.404(3) . ?
C7A C12A 1.395(4) . ?
C7A C8A 1.495(3) . ?
C9A C10A 1.389(4) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.396(4) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.384(4) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C13A C14A 1.395(3) . ?
C13A C18A 1.402(3) . ?
C14A C15A 1.382(4) . ?
C15A C16A 1.383(4) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.381(4) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.390(4) . ?
C17A H17A 0.9500 . ?
C18A H18A 0.9500 . ?
Br1B C14B 1.902(3) . ?
O1B C5B 1.211(3) . ?
O2B C8B 1.219(3) . ?
C1B C8B 1.482(4) . ?
C1B C3B 1.507(3) . ?
C1B C4B 1.508(3) . ?
C1B C2B 1.559(3) . ?
C2B C13B 1.486(4) . ?
C2B C3B 1.493(4) . ?
C2B H2B 0.9432 . ?
C3B H31B 0.9797 . ?
C3B H32B 0.9702 . ?
C4B C5B 1.510(4) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C5B C6B 1.497(4) . ?
C6B C9B 1.390(4) . ?
C6B C7B 1.405(3) . ?
C7B C12B 1.395(4) . ?
C7B C8B 1.496(3) . ?
C9B C10B 1.388(4) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.394(4) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.386(4) . ?
C11B H11B 0.9500 . ?
C12B H12B 0.9500 . ?
C13B C18B 1.390(4) . ?
C13B C14B 1.396(4) . ?
C14B C15B 1.387(4) . ?
C15B C16B 1.382(4) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.386(5) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.393(4) . ?
C17B H17B 0.9500 . ?
C18B H18B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8A C1A C3A 117.0(2) . . ?
C8A C1A C4A 116.3(2) . . ?
C3A C1A C4A 120.3(2) . . ?
C8A C1A C2A 116.4(2) . . ?
C3A C1A C2A 58.22(16) . . ?
C4A C1A C2A 115.8(2) . . ?
C13A C2A C3A 124.3(2) . . ?
C13A C2A C1A 122.5(2) . . ?
C3A C2A C1A 59.09(15) . . ?
C13A C2A H2A 108.6 . . ?
C3A C2A H2A 119.3 . . ?
C1A C2A H2A 115.4 . . ?
C2A C3A C1A 62.69(16) . . ?
C2A C3A H31A 115.1 . . ?
C1A C3A H31A 116.4 . . ?
C2A C3A H32A 133.3 . . ?
C1A C3A H32A 126.3 . . ?
H31A C3A H32A 100.8 . . ?
C5A C4A C1A 113.0(2) . . ?
C5A C4A H4AA 109.0 . . ?
C1A C4A H4AA 109.0 . . ?
C5A C4A H4AB 109.0 . . ?
C1A C4A H4AB 109.0 . . ?
H4AA C4A H4AB 107.8 . . ?
O1A C5A C6A 121.6(2) . . ?
O1A C5A C4A 121.8(2) . . ?
C6A C5A C4A 116.5(2) . . ?
C9A C6A C7A 120.1(2) . . ?
C9A C6A C5A 119.4(2) . . ?
C7A C6A C5A 120.5(2) . . ?
C12A C7A C6A 119.3(2) . . ?
C12A C7A C8A 118.9(2) . . ?
C6A C7A C8A 121.6(2) . . ?
O2A C8A C1A 122.6(2) . . ?
O2A C8A C7A 120.7(2) . . ?
C1A C8A C7A 116.6(2) . . ?
C10A C9A C6A 119.7(3) . . ?
C10A C9A H9A 120.1 . . ?
C6A C9A H9A 120.1 . . ?
C9A C10A C11A 120.6(3) . . ?
C9A C10A H10A 119.7 . . ?
C11A C10A H10A 119.7 . . ?
C12A C11A C10A 119.4(3) . . ?
C12A C11A H11A 120.3 . . ?
C10A C11A H11A 120.3 . . ?
C11A C12A C7A 120.8(3) . . ?
C11A C12A H12A 119.6 . . ?
C7A C12A H12A 119.6 . . ?
C14A C13A C18A 116.9(2) . . ?
C14A C13A C2A 120.7(2) . . ?
C18A C13A C2A 122.4(2) . . ?
C15A C14A C13A 122.7(2) . . ?
C15A C14A Br1A 117.6(2) . . ?
C13A C14A Br1A 119.77(19) . . ?
C14A C15A C16A 119.2(2) . . ?
C14A C15A H15A 120.4 . . ?
C16A C15A H15A 120.4 . . ?
C17A C16A C15A 120.0(2) . . ?
C17A C16A H16A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C16A C17A C18A 120.3(2) . . ?
C16A C17A H17A 119.8 . . ?
C18A C17A H17A 119.8 . . ?
C17A C18A C13A 121.0(2) . . ?
C17A C18A H18A 119.5 . . ?
C13A C18A H18A 119.5 . . ?
C8B C1B C3B 117.8(2) . . ?
C8B C1B C4B 117.2(2) . . ?
C3B C1B C4B 119.3(2) . . ?
C8B C1B C2B 111.5(2) . . ?
C3B C1B C2B 58.21(17) . . ?
C4B C1B C2B 119.2(2) . . ?
C13B C2B C3B 123.4(2) . . ?
C13B C2B C1B 120.6(2) . . ?
C3B C2B C1B 59.14(16) . . ?
C13B C2B H2B 117.1 . . ?
C3B C2B H2B 113.1 . . ?
C1B C2B H2B 110.2 . . ?
C2B C3B C1B 62.64(17) . . ?
C2B C3B H31B 121.9 . . ?
C1B C3B H31B 119.6 . . ?
C2B C3B H32B 113.8 . . ?
C1B C3B H32B 113.4 . . ?
H31B C3B H32B 115.2 . . ?
C1B C4B C5B 113.4(2) . . ?
C1B C4B H4BA 108.9 . . ?
C5B C4B H4BA 108.9 . . ?
C1B C4B H4BB 108.9 . . ?
C5B C4B H4BB 108.9 . . ?
H4BA C4B H4BB 107.7 . . ?
O1B C5B C6B 121.6(2) . . ?
O1B C5B C4B 122.2(2) . . ?
C6B C5B C4B 116.1(2) . . ?
C9B C6B C7B 119.8(2) . . ?
C9B C6B C5B 118.7(2) . . ?
C7B C6B C5B 121.5(2) . . ?
C12B C7B C6B 119.6(2) . . ?
C12B C7B C8B 118.8(2) . . ?
C6B C7B C8B 121.3(2) . . ?
O2B C8B C1B 122.2(2) . . ?
O2B C8B C7B 121.1(2) . . ?
C1B C8B C7B 116.4(2) . . ?
C10B C9B C6B 120.2(2) . . ?
C10B C9B H9B 119.9 . . ?
C6B C9B H9B 119.9 . . ?
C9B C10B C11B 120.0(3) . . ?
C9B C10B H10B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C12B C11B C10B 120.2(3) . . ?
C12B C11B H11B 119.9 . . ?
C10B C11B H11B 119.9 . . ?
C11B C12B C7B 120.1(2) . . ?
C11B C12B H12B 119.9 . . ?
C7B C12B H12B 119.9 . . ?
C18B C13B C14B 116.9(3) . . ?
C18B C13B C2B 121.5(2) . . ?
C14B C13B C2B 121.6(2) . . ?
C15B C14B C13B 122.3(3) . . ?
C15B C14B Br1B 117.7(2) . . ?
C13B C14B Br1B 119.9(2) . . ?
C16B C15B C14B 119.2(3) . . ?
C16B C15B H15B 120.4 . . ?
C14B C15B H15B 120.4 . . ?
C15B C16B C17B 120.3(3) . . ?
C15B C16B H16B 119.9 . . ?
C17B C16B H16B 119.9 . . ?
C16B C17B C18B 119.4(3) . . ?
C16B C17B H17B 120.3 . . ?
C18B C17B H17B 120.3 . . ?
C13B C18B C17B 121.9(3) . . ?
C13B C18B H18B 119.1 . . ?
C17B C18B H18B 119.1 . . ?

_refine_diff_density_max         0.562
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.070



####################################################################### 
# 
# 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_mo_fa0677_2_kotora
_database_code_depnum_ccdc_archive 'CCDC 2352748'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2024-05-02 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H13 N O4'
_chemical_formula_sum            'C20 H13 N O4'
_chemical_formula_weight         331.31
_chemical_compound_source        'synthesized by the authors'

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                   9.7795(3)
_cell_length_b                   14.7456(4)
_cell_length_c                   11.7028(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.1800(10)
_cell_angle_gamma                90
_cell_volume                     1551.36(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9824
_cell_measurement_theta_min      2.3108
_cell_measurement_theta_max      27.4649

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.145
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36082
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.893
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7077
_reflns_number_gt                6977
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.994

_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 Instrument Service vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0383P)²+0.3512P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3274 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(18)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         7077
_refine_ls_number_parameters     451
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0744
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.55315(16) 0.67227(10) 0.54019(13) 0.0170(3) Uani 1 1 d . . . . .
O1A O 1.00727(17) 0.70786(12) 0.96531(14) 0.0344(4) Uani 1 1 d . . . . .
O2A O 0.74979(15) 0.52384(11) 0.54204(13) 0.0283(3) Uani 1 1 d . . . . .
O3A O 0.75121(15) 0.77022(10) 0.59312(13) 0.0263(3) Uani 1 1 d . . . . .
O4A O 0.32320(14) 0.60385(9) 0.43484(12) 0.0231(3) Uani 1 1 d . . . . .
C1A C 0.73024(19) 0.57993(12) 0.72479(16) 0.0167(3) Uani 1 1 d . . . . .
C2A C 0.59055(19) 0.63929(12) 0.66316(16) 0.0169(3) Uani 1 1 d . . . . .
H2A H 0.574330 0.679630 0.720228 0.020 Uiso 1 1 d R U . . .
C3A C 0.5755(2) 0.54139(13) 0.68615(18) 0.0221(4) Uani 1 1 d . . . . .
H31A H 0.534077 0.521042 0.744927 0.027 Uiso 1 1 d R U . . .
H32A H 0.539176 0.501742 0.606027 0.027 Uiso 1 1 d R U . . .
C4A C 0.8220(2) 0.59762(13) 0.86103(16) 0.0195(3) Uani 1 1 d . . . . .
H4AA H 0.760112 0.630723 0.896897 0.023 Uiso 1 1 calc R U . . .
H4AB H 0.850227 0.538811 0.904887 0.023 Uiso 1 1 calc R U . . .
C5A C 0.96013(19) 0.65139(13) 0.88349(16) 0.0202(4) Uani 1 1 d . . . . .
C6A C 1.04293(19) 0.62664(12) 0.80486(16) 0.0182(3) Uani 1 1 d . . . . .
C7A C 0.97445(18) 0.57638(11) 0.69568(15) 0.0157(3) Uani 1 1 d . . . . .
C8A C 0.81223(19) 0.55575(12) 0.64561(16) 0.0181(3) Uani 1 1 d . . . . .
C9A C 1.1916(2) 0.65180(14) 0.84239(18) 0.0236(4) Uani 1 1 d . . . . .
H9A H 1.238149 0.686598 0.915913 0.028 Uiso 1 1 calc R U . . .
C10A C 1.2718(2) 0.62622(14) 0.77277(19) 0.0251(4) Uani 1 1 d . . . . .
H10A H 1.373031 0.643796 0.798461 0.030 Uiso 1 1 calc R U . . .
C11A C 1.2045(2) 0.57507(14) 0.66582(18) 0.0228(4) Uani 1 1 d . . . . .
H11A H 1.260106 0.557012 0.618912 0.027 Uiso 1 1 calc R U . . .
C12A C 1.0565(2) 0.55017(13) 0.62702(16) 0.0200(3) Uani 1 1 d . . . . .
H12A H 1.010764 0.515191 0.553556 0.024 Uiso 1 1 calc R U . . .
C13A C 0.63664(19) 0.74079(12) 0.51673(17) 0.0183(3) Uani 1 1 d . . . . .
C14A C 0.55472(19) 0.76752(12) 0.38501(16) 0.0184(3) Uani 1 1 d . . . . .
C15A C 0.5900(2) 0.82995(13) 0.31365(18) 0.0226(4) Uani 1 1 d . . . . .
H15A H 0.680696 0.863012 0.345784 0.027 Uiso 1 1 calc R U . . .
C16A C 0.4869(2) 0.84268(13) 0.19192(18) 0.0262(4) Uani 1 1 d . . . . .
H16A H 0.508067 0.884814 0.139660 0.031 Uiso 1 1 calc R U . . .
C17A C 0.3539(2) 0.79471(14) 0.14599(17) 0.0268(4) Uani 1 1 d . . . . .
H17A H 0.284777 0.805796 0.063457 0.032 Uiso 1 1 calc R U . . .
C18A C 0.3197(2) 0.73091(13) 0.21807(17) 0.0237(4) Uani 1 1 d . . . . .
H18A H 0.229259 0.697632 0.186316 0.028 Uiso 1 1 calc R U . . .
C19A C 0.42309(19) 0.71793(12) 0.33808(16) 0.0183(3) Uani 1 1 d . . . . .
C20A C 0.41845(18) 0.65690(12) 0.43788(16) 0.0179(3) Uani 1 1 d . . . . .
N1B N 0.21727(15) 0.34730(10) 0.01248(13) 0.0163(3) Uani 1 1 d . . . . .
O1B O 0.64696(16) 0.31998(10) 0.44367(13) 0.0295(3) Uani 1 1 d . . . . .
O2B O 0.42647(14) 0.48568(10) 0.00603(12) 0.0231(3) Uani 1 1 d . . . . .
O3B O -0.01382(15) 0.41154(10) -0.09921(12) 0.0244(3) Uani 1 1 d . . . . .
O4B O 0.42027(14) 0.25206(9) 0.07345(12) 0.0223(3) Uani 1 1 d . . . . .
C1B C 0.39240(18) 0.44571(12) 0.18923(15) 0.0165(3) Uani 1 1 d . . . . .
C2B C 0.25120(18) 0.38802(12) 0.13130(16) 0.0174(3) Uani 1 1 d . . . . .
H2B H 0.237910 0.348642 0.193589 0.021 Uiso 1 1 d R U . . .
C3B C 0.24017(19) 0.48865(13) 0.14079(18) 0.0210(4) Uani 1 1 d . . . . .
H31B H 0.208484 0.508147 0.199216 0.025 Uiso 1 1 d R U . . .
H32B H 0.206883 0.519147 0.065916 0.025 Uiso 1 1 d R U . . .
C4B C 0.47830(19) 0.43594(13) 0.32830(16) 0.0208(4) Uani 1 1 d . . . . .
H4BA H 0.510498 0.496740 0.364898 0.025 Uiso 1 1 calc R U . . .
H4BB H 0.411612 0.410466 0.365533 0.025 Uiso 1 1 calc R U . . .
C5B C 0.6122(2) 0.37610(13) 0.36085(16) 0.0197(3) Uani 1 1 d . . . . .
C6B C 0.70471(19) 0.39291(11) 0.28804(16) 0.0167(3) Uani 1 1 d . . . . .
C7B C 0.64346(18) 0.43492(11) 0.17159(16) 0.0155(3) Uani 1 1 d . . . . .
C8B C 0.48213(18) 0.45861(11) 0.11270(15) 0.0156(3) Uani 1 1 d . . . . .
C9B C 0.8546(2) 0.36768(13) 0.33641(18) 0.0241(4) Uani 1 1 d . . . . .
H9B H 0.896662 0.338479 0.414989 0.029 Uiso 1 1 calc R U . . .
C10B C 0.9419(2) 0.38500(15) 0.27048(19) 0.0278(4) Uani 1 1 d . . . . .
H10B H 1.044093 0.368535 0.304372 0.033 Uiso 1 1 calc R U . . .
C11B C 0.8805(2) 0.42652(15) 0.15454(18) 0.0251(4) Uani 1 1 d . . . . .
H11B H 0.940562 0.437697 0.109002 0.030 Uiso 1 1 calc R U . . .
C12B C 0.73234(19) 0.45157(12) 0.10538(16) 0.0192(3) Uani 1 1 d . . . . .
H12B H 0.690952 0.480189 0.026352 0.023 Uiso 1 1 calc R U . . .
C13B C 0.08347(19) 0.35887(12) -0.09228(15) 0.0172(3) Uani 1 1 d . . . . .
C14B C 0.0902(2) 0.29333(12) -0.18608(16) 0.0181(3) Uani 1 1 d . . . . .
C15B C -0.0117(2) 0.27620(13) -0.30540(17) 0.0234(4) Uani 1 1 d . . . . .
H15B H -0.100883 0.310372 -0.341534 0.028 Uiso 1 1 calc R U . . .
C16B C 0.0224(2) 0.20644(15) -0.37021(17) 0.0274(4) Uani 1 1 d . . . . .
H16B H -0.045467 0.192495 -0.452234 0.033 Uiso 1 1 calc R U . . .
C17B C 0.1535(2) 0.15671(14) -0.31761(19) 0.0274(4) Uani 1 1 d . . . . .
H17B H 0.173424 0.109514 -0.364173 0.033 Uiso 1 1 calc R U . . .
C18B C 0.2561(2) 0.17523(12) -0.19744(18) 0.0220(4) Uani 1 1 d . . . . .
H18B H 0.346263 0.142008 -0.161082 0.026 Uiso 1 1 calc R U . . .
C19B C 0.22076(19) 0.24402(12) -0.13379(16) 0.0171(3) Uani 1 1 d . . . . .
C20B C 0.30328(19) 0.27767(11) -0.00519(16) 0.0158(3) 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 C13A 1.393(2) . ?
N1A C20A 1.407(2) . ?
N1A C2A 1.424(2) . ?
O1A C5A 1.215(2) . ?
O2A C8A 1.217(2) . ?
O3A C13A 1.206(2) . ?
O4A C20A 1.206(2) . ?
C1A C8A 1.488(2) . ?
C1A C3A 1.510(2) . ?
C1A C4A 1.513(2) . ?
C1A C2A 1.542(2) . ?
C2A C3A 1.486(3) . ?
C2A H2A 0.9532 . ?
C3A H31A 0.9727 . ?
C3A H32A 1.0416 . ?
C4A C5A 1.498(3) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C5A C6A 1.491(2) . ?
C6A C9A 1.393(2) . ?
C6A C7A 1.399(2) . ?
C7A C12A 1.395(2) . ?
C7A C8A 1.490(2) . ?
C9A C10A 1.388(3) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.386(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.386(3) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C13A C14A 1.484(2) . ?
C14A C15A 1.375(3) . ?
C14A C19A 1.392(2) . ?
C15A C16A 1.397(3) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.390(3) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.389(3) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.383(2) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.489(2) . ?
N1B C20B 1.393(2) . ?
N1B C13B 1.408(2) . ?
N1B C2B 1.429(2) . ?
O1B C5B 1.217(2) . ?
O2B C8B 1.216(2) . ?
O3B C13B 1.206(2) . ?
O4B C20B 1.212(2) . ?
C1B C8B 1.492(2) . ?
C1B C3B 1.508(2) . ?
C1B C4B 1.516(2) . ?
C1B C2B 1.534(2) . ?
C2B C3B 1.495(3) . ?
C2B H2B 0.9798 . ?
C3B H31B 0.9016 . ?
C3B H32B 0.9228 . ?
C4B C5B 1.499(3) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C5B C6B 1.487(2) . ?
C6B C9B 1.398(2) . ?
C6B C7B 1.399(2) . ?
C7B C12B 1.395(2) . ?
C7B C8B 1.493(2) . ?
C9B C10B 1.381(3) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.391(3) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.382(3) . ?
C11B H11B 0.9500 . ?
C12B H12B 0.9500 . ?
C13B C14B 1.484(2) . ?
C14B C15B 1.383(2) . ?
C14B C19B 1.385(2) . ?
C15B C16B 1.394(3) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.393(3) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.396(3) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.381(2) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.485(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
C13A N1A C20A 111.98(14) . . ?
C13A N1A C2A 120.66(14) . . ?
C20A N1A C2A 125.96(15) . . ?
C8A C1A C3A 116.47(15) . . ?
C8A C1A C4A 117.15(14) . . ?
C3A C1A C4A 119.28(15) . . ?
C8A C1A C2A 116.12(15) . . ?
C3A C1A C2A 58.29(11) . . ?
C4A C1A C2A 116.35(15) . . ?
N1A C2A C3A 120.70(16) . . ?
N1A C2A C1A 119.64(15) . . ?
C3A C2A C1A 59.78(11) . . ?
N1A C2A H2A 116.6 . . ?
C3A C2A H2A 115.1 . . ?
C1A C2A H2A 112.8 . . ?
C2A C3A C1A 61.93(11) . . ?
C2A C3A H31A 121.7 . . ?
C1A C3A H31A 123.5 . . ?
C2A C3A H32A 113.9 . . ?
C1A C3A H32A 115.3 . . ?
H31A C3A H32A 112.0 . . ?
C5A C4A C1A 113.31(15) . . ?
C5A C4A H4AA 108.9 . . ?
C1A C4A H4AA 108.9 . . ?
C5A C4A H4AB 108.9 . . ?
C1A C4A H4AB 108.9 . . ?
H4AA C4A H4AB 107.7 . . ?
O1A C5A C6A 121.64(17) . . ?
O1A C5A C4A 122.51(17) . . ?
C6A C5A C4A 115.71(15) . . ?
C9A C6A C7A 119.60(16) . . ?
C9A C6A C5A 119.54(16) . . ?
C7A C6A C5A 120.83(16) . . ?
C12A C7A C6A 119.72(16) . . ?
C12A C7A C8A 118.79(15) . . ?
C6A C7A C8A 121.34(15) . . ?
O2A C8A C1A 122.06(16) . . ?
O2A C8A C7A 120.65(16) . . ?
C1A C8A C7A 117.22(15) . . ?
C10A C9A C6A 120.25(17) . . ?
C10A C9A H9A 119.9 . . ?
C6A C9A H9A 119.9 . . ?
C11A C10A C9A 120.05(17) . . ?
C11A C10A H10A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C12A C11A C10A 120.25(17) . . ?
C12A C11A H11A 119.9 . . ?
C10A C11A H11A 119.9 . . ?
C11A C12A C7A 120.10(17) . . ?
C11A C12A H12A 119.9 . . ?
C7A C12A H12A 119.9 . . ?
O3A C13A N1A 124.10(16) . . ?
O3A C13A C14A 129.70(17) . . ?
N1A C13A C14A 106.19(14) . . ?
C15A C14A C19A 121.77(17) . . ?
C15A C14A C13A 130.30(17) . . ?
C19A C14A C13A 107.92(15) . . ?
C14A C15A C16A 117.14(18) . . ?
C14A C15A H15A 121.4 . . ?
C16A C15A H15A 121.4 . . ?
C17A C16A C15A 121.09(18) . . ?
C17A C16A H16A 119.5 . . ?
C15A C16A H16A 119.5 . . ?
C18A C17A C16A 121.47(18) . . ?
C18A C17A H17A 119.3 . . ?
C16A C17A H17A 119.3 . . ?
C19A C18A C17A 117.11(18) . . ?
C19A C18A H18A 121.4 . . ?
C17A C18A H18A 121.4 . . ?
C18A C19A C14A 121.39(17) . . ?
C18A C19A C20A 130.10(17) . . ?
C14A C19A C20A 108.48(15) . . ?
O4A C20A N1A 125.68(17) . . ?
O4A C20A C19A 129.08(16) . . ?
N1A C20A C19A 105.24(14) . . ?
C20B N1B C13B 111.63(14) . . ?
C20B N1B C2B 122.12(14) . . ?
C13B N1B C2B 125.23(14) . . ?
C8B C1B C3B 116.60(15) . . ?
C8B C1B C4B 116.62(14) . . ?
C3B C1B C4B 119.42(15) . . ?
C8B C1B C2B 116.43(14) . . ?
C3B C1B C2B 58.86(11) . . ?
C4B C1B C2B 116.34(15) . . ?
N1B C2B C3B 119.58(16) . . ?
N1B C2B C1B 119.15(14) . . ?
C3B C2B C1B 59.70(11) . . ?
N1B C2B H2B 115.3 . . ?
C3B C2B H2B 119.9 . . ?
C1B C2B H2B 111.1 . . ?
C2B C3B C1B 61.44(11) . . ?
C2B C3B H31B 115.4 . . ?
C1B C3B H31B 115.6 . . ?
C2B C3B H32B 115.0 . . ?
C1B C3B H32B 119.2 . . ?
H31B C3B H32B 117.8 . . ?
C5B C4B C1B 112.85(14) . . ?
C5B C4B H4BA 109.0 . . ?
C1B C4B H4BA 109.0 . . ?
C5B C4B H4BB 109.0 . . ?
C1B C4B H4BB 109.0 . . ?
H4BA C4B H4BB 107.8 . . ?
O1B C5B C6B 121.85(17) . . ?
O1B C5B C4B 123.02(17) . . ?
C6B C5B C4B 115.08(15) . . ?
C9B C6B C7B 119.40(16) . . ?
C9B C6B C5B 120.07(16) . . ?
C7B C6B C5B 120.53(15) . . ?
C12B C7B C6B 119.83(15) . . ?
C12B C7B C8B 118.59(15) . . ?
C6B C7B C8B 121.51(15) . . ?
O2B C8B C1B 121.77(15) . . ?
O2B C8B C7B 121.01(15) . . ?
C1B C8B C7B 117.21(14) . . ?
C10B C9B C6B 120.32(17) . . ?
C10B C9B H9B 119.8 . . ?
C6B C9B H9B 119.8 . . ?
C9B C10B C11B 120.11(17) . . ?
C9B C10B H10B 119.9 . . ?
C11B C10B H10B 119.9 . . ?
C12B C11B C10B 120.20(17) . . ?
C12B C11B H11B 119.9 . . ?
C10B C11B H11B 119.9 . . ?
C11B C12B C7B 120.13(17) . . ?
C11B C12B H12B 119.9 . . ?
C7B C12B H12B 119.9 . . ?
O3B C13B N1B 125.10(16) . . ?
O3B C13B C14B 129.32(16) . . ?
N1B C13B C14B 105.57(14) . . ?
C15B C14B C19B 121.56(17) . . ?
C15B C14B C13B 129.92(17) . . ?
C19B C14B C13B 108.48(15) . . ?
C14B C15B C16B 116.88(18) . . ?
C14B C15B H15B 121.6 . . ?
C16B C15B H15B 121.6 . . ?
C17B C16B C15B 121.59(18) . . ?
C17B C16B H16B 119.2 . . ?
C15B C16B H16B 119.2 . . ?
C16B C17B C18B 120.93(18) . . ?
C16B C17B H17B 119.5 . . ?
C18B C17B H17B 119.5 . . ?
C19B C18B C17B 116.99(18) . . ?
C19B C18B H18B 121.5 . . ?
C17B C18B H18B 121.5 . . ?
C18B C19B C14B 122.04(17) . . ?
C18B C19B C20B 129.82(16) . . ?
C14B C19B C20B 108.13(15) . . ?
O4B C20B N1B 124.15(16) . . ?
O4B C20B C19B 129.73(16) . . ?
N1B C20B C19B 106.11(14) . . ?

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.033



