# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_polymorph1
_database_code_depnum_ccdc_archive 'CCDC 1588137'
loop_
_audit_author_name
_audit_author_address
'Hema M K'
;University of Mysore
India
;
_audit_update_record             
;
2020-09-19 deposited with the CCDC.	2020-09-29 downloaded from the CCDC.
;
_audit_creation_date             2020-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 Cu F3 N O3'
_chemical_formula_sum            'C19 H12 Cu F3 N O3'
_chemical_formula_weight         422.84
_chemical_melting_point          ?
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.894(3)
_cell_length_b                   10.729(4)
_cell_length_c                   11.479(4)
_cell_angle_alpha                111.357(9)
_cell_angle_beta                 104.883(11)
_cell_angle_gamma                94.191(8)
_cell_volume                     859.9(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5046
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.483
_cell_measurement_theta_min      3.098
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.320
_exptl_absorpt_correction_T_max  0.738
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_av_unetI/netI     0.0838
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5046
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.098
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  Rigaku
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2864
_reflns_number_total             3847
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'CrystalClear-SM Expert  (Rigaku)'
_computing_data_reduction        'd*trek  (Rigaku)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.933
_refine_diff_density_min         -0.944
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3847
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0651
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1137P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.1888
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C11(H11), C6(H6), C8(H8), C17(H17), C10(H10), C15(H15), C12(H12),
 C16(H16), C9(H9), C13(H13), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cu Cu 0.40991(6) 0.11782(4) 0.07924(4) 0.0414(2) Uani 1 1 d . . . . .
O1 O 0.3509(4) -0.0795(3) 0.0136(3) 0.0417(6) Uani 1 1 d . . . . .
O3 O 0.4604(4) 0.3129(3) 0.1340(3) 0.0465(7) Uani 1 1 d . . . . .
O2 O 0.5617(4) 0.1298(3) 0.2484(3) 0.0438(6) Uani 1 1 d . . . . .
N1 N 0.1915(5) 0.0971(4) -0.0626(3) 0.0434(8) Uani 1 1 d . . . . .
C2 C 0.6348(5) 0.2418(4) 0.3459(4) 0.0422(8) Uani 1 1 d . . . . .
C18 C 0.1918(5) -0.1275(4) -0.0766(4) 0.0432(9) Uani 1 1 d . . . . .
C19 C 0.1020(5) -0.0348(4) -0.1205(4) 0.0420(9) Uani 1 1 d . . . . .
C4 C 0.5521(5) 0.4035(4) 0.2449(4) 0.0423(8) Uani 1 1 d . . . . .
C5 C 0.5675(6) 0.5465(4) 0.2572(4) 0.0448(9) Uani 1 1 d . . . . .
C3 C 0.6355(6) 0.3726(4) 0.3534(4) 0.0479(10) Uani 1 1 d . . . . .
H3 H 0.693505 0.444256 0.433575 0.057 Uiso 1 1 calc R . . . .
C11 C 0.1167(6) 0.1896(5) -0.0988(4) 0.0533(11) Uani 1 1 d . . . . .
H11 H 0.176991 0.279425 -0.059253 0.064 Uiso 1 1 calc R . . . .
C14 C -0.0673(6) -0.0765(5) -0.2177(4) 0.0544(11) Uani 1 1 d . . . . .
C6 C 0.6997(7) 0.6515(5) 0.3571(5) 0.0593(12) Uani 1 1 d . . . . .
H6 H 0.780667 0.632725 0.420477 0.071 Uiso 1 1 calc R . . . .
C8 C 0.5923(8) 0.8122(5) 0.2696(5) 0.0639(13) Uani 1 1 d . . . . .
H8 H 0.599204 0.900856 0.274284 0.077 Uiso 1 1 calc R . . . .
C17 C 0.1065(6) -0.2631(5) -0.1337(4) 0.0529(11) Uani 1 1 d . . . . .
H17 H 0.161393 -0.326949 -0.108387 0.064 Uiso 1 1 calc R . . . .
C10 C 0.4520(8) 0.5791(5) 0.1633(5) 0.0664(14) Uani 1 1 d . . . . .
H10 H 0.364793 0.510685 0.094088 0.080 Uiso 1 1 calc R . . . .
C15 C -0.1467(6) -0.2152(6) -0.2711(5) 0.0649(14) Uani 1 1 d . . . . .
H15 H -0.257410 -0.245887 -0.335194 0.078 Uiso 1 1 calc R . . . .
C12 C -0.0492(7) 0.1567(6) -0.1941(5) 0.0654(13) Uani 1 1 d . . . . .
H12 H -0.097233 0.223992 -0.217397 0.079 Uiso 1 1 calc R . . . .
C16 C -0.0626(7) -0.3048(5) -0.2296(5) 0.0630(13) Uani 1 1 d . . . . .
H16 H -0.118034 -0.395697 -0.265341 0.076 Uiso 1 1 calc R . . . .
C9 C 0.4639(8) 0.7101(5) 0.1704(5) 0.0687(14) Uani 1 1 d . . . . .
H9 H 0.383615 0.729424 0.107114 0.082 Uiso 1 1 calc R . . . .
C13 C -0.1408(7) 0.0255(7) -0.2532(5) 0.0662(14) Uani 1 1 d . . . . .
H13 H -0.251316 0.003439 -0.316536 0.079 Uiso 1 1 calc R . . . .
C7 C 0.7121(8) 0.7831(5) 0.3631(5) 0.0701(14) Uani 1 1 d . . . . .
H7 H 0.801106 0.852030 0.430100 0.084 Uiso 1 1 calc R . . . .
F1 F 0.8562(5) 0.1459(4) 0.4460(3) 0.0923(11) Uani 1 1 d . . . . .
F2 F 0.6243(6) 0.1496(5) 0.5020(3) 0.1001(13) Uani 1 1 d . . . . .
F3 F 0.8101(7) 0.3328(3) 0.5720(3) 0.1178(18) Uani 1 1 d . . . . .
C1 C 0.7330(7) 0.2206(5) 0.4683(4) 0.0549(11) 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
Cu O1 2.387(3) 2_655 ?
Cu O1 1.944(3) . ?
Cu O3 1.930(3) . ?
Cu O2 1.955(3) . ?
Cu N1 1.978(3) . ?
O1 C18 1.329(5) . ?
O3 C4 1.270(5) . ?
O2 C2 1.272(4) . ?
N1 C19 1.367(5) . ?
N1 C11 1.329(5) . ?
C2 C3 1.373(6) . ?
C2 C1 1.525(5) . ?
C18 C19 1.425(6) . ?
C18 C17 1.392(6) . ?
C19 C14 1.419(5) . ?
C4 C5 1.482(5) . ?
C4 C3 1.416(6) . ?
C5 C6 1.395(6) . ?
C5 C10 1.390(6) . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.397(6) . ?
C14 C15 1.409(8) . ?
C14 C13 1.413(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.364(7) . ?
C8 C7 1.382(8) . ?
C17 H17 0.9300 . ?
C17 C16 1.412(7) . ?
C10 H10 0.9300 . ?
C10 C9 1.372(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.362(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.367(8) . ?
C16 H16 0.9300 . ?
C9 H9 0.9300 . ?
C13 H13 0.9300 . ?
C7 H7 0.9300 . ?
F1 C1 1.322(6) . ?
F2 C1 1.325(6) . ?
F3 C1 1.309(5) . ?

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
O1 Cu O1 85.36(11) . 2_655 ?
O1 Cu O2 91.60(11) . . ?
O1 Cu N1 84.30(13) . . ?
O3 Cu O1 94.28(12) . 2_655 ?
O3 Cu O1 176.53(10) . . ?
O3 Cu O2 91.86(12) . . ?
O3 Cu N1 92.54(13) . . ?
O2 Cu O1 91.41(11) . 2_655 ?
O2 Cu N1 159.65(14) . . ?
N1 Cu O1 108.05(12) . 2_655 ?
Cu O1 Cu 94.64(11) . 2_655 ?
C18 O1 Cu 112.6(2) . 2_655 ?
C18 O1 Cu 111.2(3) . . ?
C4 O3 Cu 129.0(3) . . ?
C2 O2 Cu 123.6(3) . . ?
C19 N1 Cu 110.4(3) . . ?
C11 N1 Cu 130.7(3) . . ?
C11 N1 C19 118.6(4) . . ?
O2 C2 C3 129.1(4) . . ?
O2 C2 C1 112.3(3) . . ?
C3 C2 C1 118.6(4) . . ?
O1 C18 C19 118.2(4) . . ?
O1 C18 C17 124.7(4) . . ?
C17 C18 C19 117.1(4) . . ?
N1 C19 C18 115.0(3) . . ?
N1 C19 C14 122.6(4) . . ?
C14 C19 C18 122.4(4) . . ?
O3 C4 C5 116.6(4) . . ?
O3 C4 C3 122.9(4) . . ?
C3 C4 C5 120.5(4) . . ?
C6 C5 C4 122.7(4) . . ?
C10 C5 C4 119.8(4) . . ?
C10 C5 C6 117.4(4) . . ?
C2 C3 C4 123.2(4) . . ?
C2 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
N1 C11 H11 118.8 . . ?
N1 C11 C12 122.3(5) . . ?
C12 C11 H11 118.8 . . ?
C15 C14 C19 117.7(5) . . ?
C15 C14 C13 125.7(4) . . ?
C13 C14 C19 116.6(4) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.9(5) . . ?
C7 C6 H6 119.6 . . ?
C9 C8 H8 120.2 . . ?
C9 C8 C7 119.6(4) . . ?
C7 C8 H8 120.2 . . ?
C18 C17 H17 119.7 . . ?
C18 C17 C16 120.7(5) . . ?
C16 C17 H17 119.7 . . ?
C5 C10 H10 119.3 . . ?
C9 C10 C5 121.5(5) . . ?
C9 C10 H10 119.3 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.5(4) . . ?
C16 C15 H15 119.7 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 H12 120.0 . . ?
C17 C16 H16 119.2 . . ?
C15 C16 C17 121.7(5) . . ?
C15 C16 H16 119.2 . . ?
C8 C9 C10 120.6(5) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C14 C13 H13 120.1 . . ?
C12 C13 C14 119.9(4) . . ?
C12 C13 H13 120.1 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.1(5) . . ?
C8 C7 H7 120.0 . . ?
F1 C1 C2 111.2(4) . . ?
F1 C1 F2 104.2(4) . . ?
F2 C1 C2 111.3(4) . . ?
F3 C1 C2 114.8(4) . . ?
F3 C1 F1 107.7(5) . . ?
F3 C1 F2 107.0(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_polymorph2
_database_code_depnum_ccdc_archive 'CCDC 1969090'
loop_
_audit_author_name
_audit_author_address
'Mahesha '
;University of Mysore
India
;
_audit_update_record             
;
2020-09-12 deposited with the CCDC.	2020-09-29 downloaded from the CCDC.
;
_audit_creation_date             2020-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H12 Cu F3 N O3), 2(C2 H4 O2)'
_chemical_formula_sum            'C42 H32 Cu2 F6 N2 O10'
_chemical_formula_weight         965.77
_chemical_melting_point          ?
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/a 1'
_space_group_name_Hall           '-P 2yab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   8.560(2)
_cell_length_b                   22.750(5)
_cell_length_c                   11.020(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.640(3)
_cell_angle_gamma                90
_cell_volume                     1994.8(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10973
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.507
_cell_measurement_theta_min      3.156
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.157
_exptl_absorpt_correction_T_max  0.784
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1259
_diffrn_reflns_av_unetI/netI     0.1322
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10973
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         3.156
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  Rigaku
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2402
_reflns_number_total             4457
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'CrystalClear-SM Expert  (Rigaku)'
_computing_data_reduction        'd*trek  (Rigaku)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0847
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1114P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2083
_refine_ls_wR_factor_ref         0.2506
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C3(H3), C15(H15), C16(H16), C17(H17), C10(H10), C6(H6),
 C13(H13), C12(H12), C7(H7), C9(H9)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
2.c Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cu1 Cu 0.58993(9) 0.65266(3) 0.73671(7) 0.0538(3) Uani 1 1 d . . . . .
O3 O 0.6053(6) 0.57475(15) 0.8082(4) 0.0618(11) Uani 1 1 d . . . . .
O1 O 0.6026(5) 0.73483(16) 0.6926(4) 0.0559(10) Uani 1 1 d . . . . .
O2 O 0.6547(5) 0.62590(16) 0.5960(4) 0.0573(10) Uani 1 1 d . . . . .
C8 C 0.8623(11) 0.5556(4) 0.2572(7) 0.086(2) Uani 1 1 d . . . . .
H8 H 0.903447 0.551679 0.190444 0.104 Uiso 1 1 calc R . . . .
O4 O 0.2946(6) 0.65226(18) 0.5805(5) 0.0671(12) Uani 1 1 d . . . . .
N1 N 0.5307(6) 0.68510(19) 0.8806(4) 0.0496(11) Uani 1 1 d . . . . .
C11 C 0.4983(9) 0.6571(2) 0.9731(6) 0.0598(16) Uani 1 1 d . . . . .
H11 H 0.504314 0.616280 0.976598 0.072 Uiso 1 1 calc R . . . .
O5 O 0.1727(7) 0.7361(2) 0.4910(4) 0.0796(14) Uani 1 1 d . . . . .
H5 H 0.149159 0.737496 0.556601 0.119 Uiso 1 1 calc GR . . . .
C3 C 0.7055(8) 0.5262(2) 0.6598(6) 0.0578(15) Uani 1 1 d . . . . .
H3 H 0.742263 0.490024 0.641133 0.069 Uiso 1 1 calc R . . . .
C4 C 0.6960(7) 0.5746(3) 0.5749(5) 0.0532(13) Uani 1 1 d . . . . .
C19 C 0.5252(7) 0.7451(2) 0.8738(5) 0.0488(12) Uani 1 1 d . . . . .
C14 C 0.4821(8) 0.7790(3) 0.9670(6) 0.0564(14) Uani 1 1 d . . . . .
C15 C 0.4800(9) 0.8409(2) 0.9514(7) 0.0642(17) Uani 1 1 d . . . . .
H15 H 0.451495 0.864968 1.008218 0.077 Uiso 1 1 calc R . . . .
F1 F 0.7010(14) 0.43001(19) 0.8087(6) 0.198(4) Uani 1 1 d . . . . .
C5 C 0.7532(7) 0.5669(3) 0.4633(5) 0.0539(14) Uani 1 1 d . . . . .
C16 C 0.5190(8) 0.8647(3) 0.8551(6) 0.0629(16) Uani 1 1 d . . . . .
H16 H 0.516203 0.905385 0.847523 0.075 Uiso 1 1 calc R . . . .
C17 C 0.5637(8) 0.8320(2) 0.7651(6) 0.0586(15) Uani 1 1 d . . . . .
H17 H 0.592077 0.850648 0.701014 0.070 Uiso 1 1 calc R . . . .
F3 F 0.5790(9) 0.4717(3) 0.9096(8) 0.167(3) Uani 1 1 d . . . . .
C2 C 0.6626(8) 0.5307(2) 0.7676(6) 0.0552(14) Uani 1 1 d . . . . .
C10 C 0.7930(8) 0.6167(3) 0.4100(6) 0.0670(17) Uani 1 1 d . . . . .
H10 H 0.783703 0.653727 0.442631 0.080 Uiso 1 1 calc R . . . .
C6 C 0.7663(9) 0.5127(3) 0.4123(7) 0.0714(18) Uani 1 1 d . . . . .
H6 H 0.740653 0.479141 0.449374 0.086 Uiso 1 1 calc R . . . .
C1 C 0.6880(10) 0.4782(3) 0.8558(6) 0.0640(17) Uani 1 1 d . . . . .
C21 C 0.2549(9) 0.6874(3) 0.4918(7) 0.0634(16) Uani 1 1 d . . . . .
C13 C 0.4440(9) 0.7476(3) 1.0629(6) 0.0685(17) Uani 1 1 d . . . . .
H13 H 0.411639 0.767676 1.123300 0.082 Uiso 1 1 calc R . . . .
C18 C 0.5646(7) 0.7704(2) 0.7737(6) 0.0530(13) Uani 1 1 d . . . . .
C12 C 0.4545(9) 0.6880(3) 1.0670(6) 0.0683(17) Uani 1 1 d . . . . .
H12 H 0.432718 0.667434 1.131981 0.082 Uiso 1 1 calc R . . . .
C7 C 0.8159(10) 0.5071(4) 0.3084(7) 0.088(2) Uani 1 1 d . . . . .
H7 H 0.818122 0.470259 0.272681 0.105 Uiso 1 1 calc R . . . .
C9 C 0.8481(10) 0.6106(4) 0.3049(7) 0.088(2) Uani 1 1 d . . . . .
H9 H 0.874958 0.643834 0.267454 0.105 Uiso 1 1 calc R . . . .
F2 F 0.8245(10) 0.4843(3) 0.9574(7) 0.185(4) Uani 1 1 d . . . . .
C20 C 0.2986(11) 0.6807(4) 0.3736(7) 0.090(2) Uani 1 1 d . . . . .
H20A H 0.384937 0.651563 0.389666 0.134 Uiso 1 1 calc GR . . . .
H20B H 0.338294 0.717628 0.353896 0.134 Uiso 1 1 calc GR . . . .
H20C H 0.200688 0.668739 0.301077 0.134 Uiso 1 1 calc GR . . . .


_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
Cu1 O3 1.924(4) . ?
Cu1 O1 1.945(4) . ?
Cu1 O2 1.928(4) . ?
Cu1 N1 1.977(5) . ?
O3 C2 1.267(6) . ?
O1 C18 1.332(7) . ?
O2 C4 1.265(6) . ?
C8 C7 1.364(11) . ?
C8 C9 1.379(11) . ?
O4 C21 1.210(8) . ?
N1 C11 1.315(7) . ?
N1 C19 1.366(7) . ?
C11 C12 1.411(9) . ?
O5 C21 1.310(7) . ?
C3 C4 1.429(8) . ?
C3 C2 1.370(8) . ?
C4 C5 1.492(8) . ?
C19 C14 1.438(8) . ?
C19 C18 1.392(8) . ?
C14 C15 1.418(8) . ?
C14 C13 1.409(9) . ?
C15 C16 1.338(9) . ?
F1 C1 1.236(7) . ?
C5 C10 1.376(8) . ?
C5 C6 1.377(8) . ?
C16 C17 1.402(9) . ?
C17 C18 1.403(7) . ?
F3 C1 1.285(8) . ?
C2 C1 1.505(8) . ?
C10 C9 1.409(9) . ?
C6 C7 1.366(10) . ?
C1 F2 1.293(8) . ?
C21 C20 1.490(9) . ?
C13 C12 1.359(9) . ?

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
O3 Cu1 O1 170.44(17) . . ?
O3 Cu1 O2 92.40(16) . . ?
O3 Cu1 N1 90.84(17) . . ?
O1 Cu1 N1 84.04(17) . . ?
O2 Cu1 O1 92.48(16) . . ?
O2 Cu1 N1 176.22(17) . . ?
C2 O3 Cu1 124.1(4) . . ?
C18 O1 Cu1 111.5(3) . . ?
C4 O2 Cu1 128.4(4) . . ?
C7 C8 C9 119.7(7) . . ?
C11 N1 Cu1 129.1(4) . . ?
C11 N1 C19 120.9(5) . . ?
C19 N1 Cu1 110.0(4) . . ?
N1 C11 C12 121.1(5) . . ?
C2 C3 C4 122.7(5) . . ?
O2 C4 C3 122.9(5) . . ?
O2 C4 C5 117.3(5) . . ?
C3 C4 C5 119.5(5) . . ?
N1 C19 C14 120.6(5) . . ?
N1 C19 C18 116.4(5) . . ?
C18 C19 C14 123.0(5) . . ?
C15 C14 C19 116.2(6) . . ?
C13 C14 C19 117.1(5) . . ?
C13 C14 C15 126.7(6) . . ?
C16 C15 C14 120.1(6) . . ?
C10 C5 C4 117.6(5) . . ?
C10 C5 C6 119.5(6) . . ?
C6 C5 C4 122.8(6) . . ?
C15 C16 C17 124.0(6) . . ?
C16 C17 C18 118.5(6) . . ?
O3 C2 C3 128.9(5) . . ?
O3 C2 C1 112.4(5) . . ?
C3 C2 C1 118.6(5) . . ?
C5 C10 C9 118.7(7) . . ?
C7 C6 C5 121.5(7) . . ?
F1 C1 F3 106.6(7) . . ?
F1 C1 C2 116.5(5) . . ?
F1 C1 F2 105.4(8) . . ?
F3 C1 C2 115.6(6) . . ?
F3 C1 F2 101.0(7) . . ?
F2 C1 C2 110.1(6) . . ?
O4 C21 O5 123.7(6) . . ?
O4 C21 C20 123.6(6) . . ?
O5 C21 C20 112.7(6) . . ?
C12 C13 C14 120.0(6) . . ?
O1 C18 C19 118.1(5) . . ?
O1 C18 C17 123.9(6) . . ?
C19 C18 C17 118.0(6) . . ?
C13 C12 C11 120.3(6) . . ?
C8 C7 C6 120.0(7) . . ?
C8 C9 C10 120.4(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
