# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 1978225'
_audit_update_record             
;
2020-01-16 deposited with the CCDC.	2022-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 Cu F N O4'
_chemical_formula_weight         290.73

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   7.6004(3)
_cell_length_b                   14.1706(5)
_cell_length_c                   20.2294(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2178.75(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      30.85

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   0.602
_exptl_transmission_factor_max   0.688
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.020
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28014
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.013
_diffrn_reflns_theta_max         31.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3486
_reflns_number_gt                2891
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.1330P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3486
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
Cu1 Cu 0.53411(3) 0.39871(2) 0.48049(2) 0.02770(11) Uani 1 1 d . . . . .
O1 O 0.43291(16) 0.51576(8) 0.44362(5) 0.0244(2) Uani 1 1 d . . . . .
O2 O 0.6818(2) 0.28940(9) 0.50442(7) 0.0339(3) Uani 1 1 d . . . . .
O3 O 0.76647(19) 0.14922(9) 0.46633(9) 0.0403(3) Uani 1 1 d . . . . .
F1 F 0.3246(3) 0.73113(10) 0.27102(7) 0.0635(5) Uani 1 1 d . . . . .
N1 N 0.4907(2) 0.32789(11) 0.40123(8) 0.0277(3) Uani 1 1 d . . . . .
O4 O 0.7999(2) 0.47068(12) 0.41406(11) 0.0571(5) Uani 1 1 d . . . . .
H4 H 0.796100 0.523979 0.429776 0.086 Uiso 1 1 calc R U . . .
C6 C 0.3978(2) 0.45821(12) 0.33228(8) 0.0275(3) Uani 1 1 d . . . . .
C7 C 0.4414(2) 0.36129(13) 0.34581(9) 0.0304(4) Uani 1 1 d . . . . .
H7 H 0.432715 0.319065 0.310768 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4055(2) 0.53204(11) 0.37945(8) 0.0237(3) Uani 1 1 d . . . . .
C9 C 0.6765(2) 0.22168(12) 0.46335(9) 0.0281(3) Uani 1 1 d . . . . .
C1 C 0.3829(3) 0.62486(14) 0.35674(9) 0.0332(4) Uani 1 1 d . . . . .
H1 H 0.394714 0.675552 0.385605 0.040 Uiso 1 1 calc R U . . .
C4 C 0.3538(3) 0.47945(15) 0.26619(9) 0.0375(4) Uani 1 1 d . . . . .
H4A H 0.346000 0.430381 0.235803 0.045 Uiso 1 1 calc R U . . .
C2 C 0.3432(3) 0.63986(14) 0.29128(10) 0.0407(5) Uani 1 1 d . . . . .
C3 C 0.3222(3) 0.56951(18) 0.24523(9) 0.0440(5) Uani 1 1 d . . . . .
H3 H 0.288218 0.582518 0.202020 0.053 Uiso 1 1 calc R U . . .
C8 C 0.5424(3) 0.22983(14) 0.40799(10) 0.0345(4) Uani 1 1 d . . . . .
H8A H 0.593058 0.207404 0.366887 0.041 Uiso 1 1 calc R U . . .
H8B H 0.440131 0.191441 0.418042 0.041 Uiso 1 1 calc R U . . .
C10 C 0.9719(3) 0.4390(3) 0.41389(19) 0.0703(9) Uani 1 1 d . . . . .
H10A H 1.034006 0.466886 0.377467 0.105 Uiso 1 1 calc R U . . .
H10B H 0.973245 0.371571 0.409505 0.105 Uiso 1 1 calc R U . . .
H10C H 1.027967 0.456624 0.454595 0.105 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
Cu1 N1 1.9202(15) . ?
Cu1 O1 1.9720(11) 5_666 ?
Cu1 O2 1.9734(13) . ?
Cu1 O1 1.9746(12) . ?
Cu1 O3 2.3993(14) 4_456 ?
Cu1 Cu1 3.0220(4) 5_666 ?
O1 C5 1.3349(19) . ?
O2 C9 1.270(2) . ?
O3 C9 1.235(2) . ?
F1 C2 1.364(2) . ?
N1 C7 1.273(2) . ?
N1 C8 1.450(2) . ?
O4 C10 1.382(3) . ?
O4 H4 0.8200 . ?
C6 C4 1.411(2) . ?
C6 C5 1.417(2) . ?
C6 C7 1.439(3) . ?
C7 H7 0.9300 . ?
C5 C1 1.404(2) . ?
C9 C8 1.519(3) . ?
C1 C2 1.375(3) . ?
C1 H1 0.9300 . ?
C4 C3 1.366(3) . ?
C4 H4A 0.9300 . ?
C2 C3 1.374(3) . ?
C3 H3 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
N1 Cu1 O1 173.31(6) . 5_666 ?
N1 Cu1 O2 83.81(6) . . ?
O1 Cu1 O2 102.66(5) 5_666 . ?
N1 Cu1 O1 93.26(6) . . ?
O1 Cu1 O1 80.06(5) 5_666 . ?
O2 Cu1 O1 166.81(6) . . ?
N1 Cu1 O3 94.64(6) . 4_456 ?
O1 Cu1 O3 86.14(5) 5_666 4_456 ?
O2 Cu1 O3 98.63(6) . 4_456 ?
O1 Cu1 O3 94.41(5) . 4_456 ?
N1 Cu1 Cu1 133.25(5) . 5_666 ?
O1 Cu1 Cu1 40.06(3) 5_666 5_666 ?
O2 Cu1 Cu1 141.18(4) . 5_666 ?
O1 Cu1 Cu1 40.00(3) . 5_666 ?
O3 Cu1 Cu1 90.36(3) 4_456 5_666 ?
C5 O1 Cu1 132.13(10) . 5_666 ?
C5 O1 Cu1 124.98(10) . . ?
Cu1 O1 Cu1 99.94(5) 5_666 . ?
C9 O2 Cu1 114.49(11) . . ?
C9 O3 Cu1 136.60(13) . 4_556 ?
C7 N1 C8 121.26(15) . . ?
C7 N1 Cu1 126.26(13) . . ?
C8 N1 Cu1 112.06(12) . . ?
C10 O4 H4 109.5 . . ?
C4 C6 C5 119.36(16) . . ?
C4 C6 C7 116.00(16) . . ?
C5 C6 C7 124.55(15) . . ?
N1 C7 C6 126.16(16) . . ?
N1 C7 H7 116.9 . . ?
C6 C7 H7 116.9 . . ?
O1 C5 C1 119.94(15) . . ?
O1 C5 C6 122.25(14) . . ?
C1 C5 C6 117.81(15) . . ?
O3 C9 O2 125.36(17) . . ?
O3 C9 C8 118.09(17) . . ?
O2 C9 C8 116.51(15) . . ?
C2 C1 C5 119.13(18) . . ?
C2 C1 H1 120.4 . . ?
C5 C1 H1 120.4 . . ?
C3 C4 C6 122.36(19) . . ?
C3 C4 H4A 118.8 . . ?
C6 C4 H4A 118.8 . . ?
F1 C2 C3 118.18(18) . . ?
F1 C2 C1 117.31(19) . . ?
C3 C2 C1 124.51(18) . . ?
C4 C3 C2 116.56(17) . . ?
C4 C3 H3 121.7 . . ?
C2 C3 H3 121.7 . . ?
N1 C8 C9 108.90(14) . . ?
N1 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
N1 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
C8 N1 C7 C6 -175.92(17) . . . . ?
Cu1 N1 C7 C6 -4.0(3) . . . . ?
C4 C6 C7 N1 177.31(19) . . . . ?
C5 C6 C7 N1 0.7(3) . . . . ?
Cu1 O1 C5 C1 -4.7(2) 5_666 . . . ?
Cu1 O1 C5 C1 -161.20(12) . . . . ?
Cu1 O1 C5 C6 175.36(12) 5_666 . . . ?
Cu1 O1 C5 C6 18.9(2) . . . . ?
C4 C6 C5 O1 174.71(16) . . . . ?
C7 C6 C5 O1 -8.8(3) . . . . ?
C4 C6 C5 C1 -5.2(3) . . . . ?
C7 C6 C5 C1 171.25(17) . . . . ?
Cu1 O3 C9 O2 -19.9(3) 4_556 . . . ?
Cu1 O3 C9 C8 162.84(15) 4_556 . . . ?
Cu1 O2 C9 O3 175.22(16) . . . . ?
Cu1 O2 C9 C8 -7.5(2) . . . . ?
O1 C5 C1 C2 -175.71(17) . . . . ?
C6 C5 C1 C2 4.2(3) . . . . ?
C5 C6 C4 C3 1.7(3) . . . . ?
C7 C6 C4 C3 -175.1(2) . . . . ?
C5 C1 C2 F1 -179.18(18) . . . . ?
C5 C1 C2 C3 0.4(3) . . . . ?
C6 C4 C3 C2 2.9(3) . . . . ?
F1 C2 C3 C4 175.6(2) . . . . ?
C1 C2 C3 C4 -4.0(4) . . . . ?
C7 N1 C8 C9 150.95(17) . . . . ?
Cu1 N1 C8 C9 -22.02(19) . . . . ?
O3 C9 C8 N1 -163.03(17) . . . . ?
O2 C9 C8 N1 19.5(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
_geom_hbond_publ_flag
C8 H8B O2 0.97 2.53 3.275(2) 133.8 4_456 yes
C1 H1 O2 0.93 2.35 3.099(2) 137.1 5_666 yes
C7 H7 F1 0.93 2.45 3.127(2) 129.3 8_655 yes
O4 H4 O3 0.82 1.98 2.788(2) 168.1 8_765 yes

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.791
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_1_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1978226'
_audit_update_record             
;
2020-01-16 deposited with the CCDC.	2022-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 Cu F N O4'
_chemical_formula_weight         304.76

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   7.7611(12)
_cell_length_b                   14.453(2)
_cell_length_c                   20.556(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2305.8(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5420
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      28.64

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   0.571
_exptl_transmission_factor_max   0.636
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    1.913
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29254
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.981
_diffrn_reflns_theta_max         30.092
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3354
_reflns_number_gt                2530
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.5614P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3354
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0852
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
Cu1 Cu 0.45053(3) 0.40288(2) 0.52051(2) 0.02599(9) Uani 1 1 d . . . . .
O1 O 0.56313(16) 0.51436(8) 0.55576(6) 0.0226(3) Uani 1 1 d . . . . .
O2 O 0.30501(19) 0.29753(9) 0.49552(7) 0.0292(3) Uani 1 1 d . . . . .
F1 F 0.7119(3) 0.72285(10) 0.72315(7) 0.0636(5) Uani 1 1 d . . . . .
O3 O 0.2208(2) 0.15798(10) 0.52937(8) 0.0383(4) Uani 1 1 d . . . . .
N1 N 0.4868(2) 0.33284(10) 0.59870(8) 0.0251(3) Uani 1 1 d . . . . .
C7 C 0.5355(3) 0.36473(14) 0.65331(10) 0.0286(4) Uani 1 1 d . . . . .
H7 H 0.537650 0.323760 0.688186 0.034 Uiso 1 1 calc R U . . .
C6 C 0.5880(3) 0.45907(13) 0.66609(9) 0.0260(4) Uani 1 1 d . . . . .
C5 C 0.5933(2) 0.53028(13) 0.61866(9) 0.0222(4) Uani 1 1 d . . . . .
C9 C 0.3084(3) 0.22938(13) 0.53488(10) 0.0260(4) Uani 1 1 d . . . . .
C4 C 0.6328(3) 0.62019(14) 0.64001(10) 0.0314(5) Uani 1 1 d . . . . .
H4 H 0.630137 0.669527 0.610978 0.038 Uiso 1 1 calc R U . . .
C1 C 0.6375(3) 0.47893(15) 0.73031(10) 0.0371(5) Uani 1 1 d . . . . .
H1 H 0.639597 0.431004 0.760487 0.045 Uiso 1 1 calc R U . . .
C3 C 0.6752(3) 0.63464(15) 0.70404(10) 0.0380(5) Uani 1 1 d . . . . .
C8 C 0.4331(3) 0.23635(13) 0.59138(11) 0.0324(5) Uani 1 1 d . . . . .
H8A H 0.377927 0.215156 0.631010 0.039 Uiso 1 1 calc R U . . .
H8B H 0.532912 0.197605 0.583301 0.039 Uiso 1 1 calc R U . . .
C2 C 0.6829(3) 0.56582(17) 0.75028(10) 0.0419(6) Uani 1 1 d . . . . .
H2 H 0.717092 0.577806 0.792818 0.050 Uiso 1 1 calc R U . . .
C10 C 0.0240(3) 0.4690(2) 0.59101(16) 0.0555(7) Uani 1 1 d . . . . .
H10A H -0.038339 0.484007 0.551492 0.067 Uiso 1 1 calc R U . . .
H10B H -0.020055 0.507758 0.625741 0.067 Uiso 1 1 calc R U . . .
C11 C -0.0039(4) 0.3705(2) 0.60756(16) 0.0605(8) Uani 1 1 d . . . . .
H11A H 0.023980 0.332644 0.570639 0.091 Uiso 1 1 calc R U . . .
H11B H -0.122332 0.361092 0.619263 0.091 Uiso 1 1 calc R U . . .
H11C H 0.068692 0.353773 0.643511 0.091 Uiso 1 1 calc R U . . .
O4 O 0.1993(2) 0.48637(12) 0.58210(11) 0.0552(5) Uani 1 1 d . . . . .
H4A H 0.212261 0.538937 0.567917 0.083 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
Cu1 N1 1.9203(16) . ?
Cu1 O2 1.9641(14) . ?
Cu1 O1 1.9710(13) . ?
Cu1 O1 1.9749(13) 5_666 ?
Cu1 Cu1 3.0301(6) 5_666 ?
O1 C5 1.334(2) . ?
O2 C9 1.275(2) . ?
F1 C3 1.364(2) . ?
O3 C9 1.241(2) . ?
N1 C7 1.271(3) . ?
N1 C8 1.463(2) . ?
C7 C6 1.447(3) . ?
C7 H7 0.9300 . ?
C6 C1 1.405(3) . ?
C6 C5 1.418(3) . ?
C5 C4 1.405(3) . ?
C9 C8 1.516(3) . ?
C4 C3 1.373(3) . ?
C4 H4 0.9300 . ?
C1 C2 1.367(3) . ?
C1 H1 0.9300 . ?
C3 C2 1.377(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C2 H2 0.9300 . ?
C10 O4 1.396(3) . ?
C10 C11 1.479(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O4 H4A 0.8200 . ?

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
N1 Cu1 O2 83.95(6) . . ?
N1 Cu1 O1 93.33(6) . . ?
O2 Cu1 O1 170.00(6) . . ?
N1 Cu1 O1 172.59(6) . 5_666 ?
O2 Cu1 O1 103.36(6) . 5_666 ?
O1 Cu1 O1 79.66(6) . 5_666 ?
N1 Cu1 Cu1 133.16(5) . 5_666 ?
O2 Cu1 Cu1 142.30(4) . 5_666 ?
O1 Cu1 Cu1 39.88(4) . 5_666 ?
O1 Cu1 Cu1 39.78(4) 5_666 5_666 ?
C5 O1 Cu1 125.12(11) . . ?
C5 O1 Cu1 132.41(12) . 5_666 ?
Cu1 O1 Cu1 100.33(6) . 5_666 ?
C9 O2 Cu1 114.91(13) . . ?
C7 N1 C8 121.40(17) . . ?
C7 N1 Cu1 126.28(14) . . ?
C8 N1 Cu1 112.00(13) . . ?
N1 C7 C6 125.85(18) . . ?
N1 C7 H7 117.1 . . ?
C6 C7 H7 117.1 . . ?
C1 C6 C5 119.33(18) . . ?
C1 C6 C7 116.12(18) . . ?
C5 C6 C7 124.56(17) . . ?
O1 C5 C4 120.03(16) . . ?
O1 C5 C6 122.41(17) . . ?
C4 C5 C6 117.56(17) . . ?
O3 C9 O2 124.98(19) . . ?
O3 C9 C8 118.37(17) . . ?
O2 C9 C8 116.62(17) . . ?
C3 C4 C5 119.49(19) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C2 C1 C6 122.7(2) . . ?
C2 C1 H1 118.6 . . ?
C6 C1 H1 118.6 . . ?
F1 C3 C4 117.9(2) . . ?
F1 C3 C2 117.9(2) . . ?
C4 C3 C2 124.2(2) . . ?
N1 C8 C9 108.91(15) . . ?
N1 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
N1 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C1 C2 C3 116.4(2) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 121.8 . . ?
O4 C10 C11 110.2(2) . . ?
O4 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
O4 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 O4 H4A 109.5 . . ?

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
C8 N1 C7 C6 -178.80(19) . . . . ?
Cu1 N1 C7 C6 -5.8(3) . . . . ?
N1 C7 C6 C1 -179.8(2) . . . . ?
N1 C7 C6 C5 -0.3(3) . . . . ?
Cu1 O1 C5 C4 -163.61(14) . . . . ?
Cu1 O1 C5 C4 -3.7(3) 5_666 . . . ?
Cu1 O1 C5 C6 16.6(2) . . . . ?
Cu1 O1 C5 C6 176.58(13) 5_666 . . . ?
C1 C6 C5 O1 173.80(18) . . . . ?
C7 C6 C5 O1 -5.7(3) . . . . ?
C1 C6 C5 C4 -6.0(3) . . . . ?
C7 C6 C5 C4 174.57(19) . . . . ?
Cu1 O2 C9 O3 176.98(16) . . . . ?
Cu1 O2 C9 C8 -4.7(2) . . . . ?
O1 C5 C4 C3 -175.5(2) . . . . ?
C6 C5 C4 C3 4.2(3) . . . . ?
C5 C6 C1 C2 3.5(3) . . . . ?
C7 C6 C1 C2 -177.0(2) . . . . ?
C5 C4 C3 F1 -179.7(2) . . . . ?
C5 C4 C3 C2 0.2(4) . . . . ?
C7 N1 C8 C9 153.43(19) . . . . ?
Cu1 N1 C8 C9 -20.5(2) . . . . ?
O3 C9 C8 N1 -164.98(18) . . . . ?
O2 C9 C8 N1 16.6(3) . . . . ?
C6 C1 C2 C3 1.0(4) . . . . ?
F1 C3 C2 C1 177.0(2) . . . . ?
C4 C3 C2 C1 -2.9(4) . . . . ?

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
_geom_hbond_publ_flag
C7 H7 F1 0.93 2.53 3.180(3) 126.8 8_755 yes
C4 H4 O2 0.93 2.30 3.067(3) 140.0 5_666 yes
O4 H4A O3 0.82 1.96 2.777(2) 170.9 8_665 yes
C7 H7 F1 0.93 2.53 3.180(3) 126.8 8_755 yes
C4 H4 O2 0.93 2.30 3.067(3) 140.0 5_666 yes
O4 H4A O3 0.82 1.96 2.777(2) 170.9 8_665 yes
C7 H7 F1 0.93 2.53 3.180(3) 126.8 8_755 yes
C4 H4 O2 0.93 2.30 3.067(3) 140.0 5_666 yes
O4 H4A O3 0.82 1.96 2.777(2) 170.9 8_665 yes

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_1_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1978228'
_audit_update_record             
;
2020-01-16 deposited with the CCDC.	2022-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Cu2 F2 N2 O9'
_chemical_formula_weight         571.42

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   17.218(13)
_cell_length_b                   6.780(5)
_cell_length_c                   17.448(10)
_cell_angle_alpha                90
_cell_angle_beta                 110.89(2)
_cell_angle_gamma                90
_cell_volume                     1903(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1092
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      27.52

_exptl_crystal_description       rodlike
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.995
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   0.498
_exptl_transmission_factor_max   0.630
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    2.315
_shelx_estimated_absorpt_T_min   0.498
_shelx_estimated_absorpt_T_max   0.630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4203
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.499
_diffrn_reflns_theta_max         31.530
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2643
_reflns_number_gt                1911
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.7256P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2643
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1765
_refine_ls_wR_factor_gt          0.1571
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
Cu1 Cu 0.37756(3) 0.40962(8) 0.29599(3) 0.0232(2) Uani 1 1 d . . . . .
F1 F 0.72576(17) 0.0796(5) 0.55626(19) 0.0434(8) Uani 1 1 d . . . . .
O1 O 0.49040(17) 0.3299(5) 0.35023(18) 0.0259(7) Uani 1 1 d . . . . .
O3 O 0.27224(18) 0.5508(5) 0.25430(19) 0.0285(7) Uani 1 1 d . . . . .
O4 O 0.1604(2) 0.6249(5) 0.2840(2) 0.0342(8) Uani 1 1 d . . . . .
N1 N 0.3481(2) 0.3647(5) 0.3910(2) 0.0216(7) Uani 1 1 d . . . . .
O5 O 1.000000 0.4107(8) 0.250000 0.0616(19) Uani 1 2 d S T P . .
H5C H 0.959150 0.488246 0.242520 0.074 Uiso 0.5 1 d R U P . .
H5D H 0.981010 0.294376 0.238570 0.074 Uiso 0.5 1 d R U P . .
C6 C 0.4843(2) 0.2680(6) 0.4845(2) 0.0209(8) Uani 1 1 d . . . . .
C3 C 0.5284(3) 0.2079(6) 0.5657(3) 0.0235(8) Uani 1 1 d . . . . .
H3 H 0.501348 0.209154 0.603297 0.028 Uiso 1 1 calc R U . . .
C7 C 0.3975(2) 0.3189(6) 0.4633(3) 0.0229(8) Uani 1 1 d . . . . .
H7 H 0.375988 0.318468 0.505179 0.028 Uiso 1 1 calc R U . . .
C9 C 0.2283(3) 0.5420(7) 0.2988(3) 0.0268(9) Uani 1 1 d . . . . .
C1 C 0.6468(2) 0.1466(6) 0.5338(3) 0.0262(9) Uani 1 1 d . . . . .
C5 C 0.5248(2) 0.2692(6) 0.4271(2) 0.0203(8) Uani 1 1 d . . . . .
C8 C 0.2615(2) 0.4140(6) 0.3760(3) 0.0241(9) Uani 1 1 d . . . . .
H8A H 0.257260 0.484978 0.422623 0.029 Uiso 1 1 calc R U . . .
H8B H 0.228735 0.294234 0.368560 0.029 Uiso 1 1 calc R U . . .
C4 C 0.6077(3) 0.2060(6) 0.4541(3) 0.0279(9) Uani 1 1 d . . . . .
H4 H 0.636318 0.204327 0.417884 0.033 Uiso 1 1 calc R U . . .
C2 C 0.6097(3) 0.1476(7) 0.5914(3) 0.0287(10) Uani 1 1 d . . . . .
H2 H 0.638319 0.109337 0.645352 0.034 Uiso 1 1 calc R U . . .
O2 O 0.4044(2) 0.5224(6) 0.2026(2) 0.0423(9) Uani 1 1 d . . . . .
H2B H 0.434944 0.442481 0.188496 0.051 Uiso 1 1 d R U . . .
H2C H 0.430804 0.630001 0.217266 0.051 Uiso 1 1 d 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
Cu1 O1 1.911(3) . ?
Cu1 N1 1.923(4) . ?
Cu1 O3 1.948(3) . ?
Cu1 O2 1.998(4) . ?
Cu1 O4 2.335(4) 4_545 ?
F1 C1 1.352(5) . ?
O1 C5 1.324(5) . ?
O3 C9 1.263(6) . ?
O4 C9 1.239(5) . ?
N1 C7 1.283(5) . ?
N1 C8 1.459(5) . ?
O5 H5C 0.8500 . ?
O5 H5D 0.8500 . ?
O5 H5C 0.8500 2_755 ?
O5 H5D 0.8500 2_755 ?
C6 C3 1.408(5) . ?
C6 C5 1.410(6) . ?
C6 C7 1.448(5) . ?
C3 C2 1.372(6) . ?
C3 H3 0.9300 . ?
C7 H7 0.9300 . ?
C9 C8 1.531(6) . ?
C1 C2 1.369(7) . ?
C1 C4 1.372(6) . ?
C5 C4 1.401(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
O2 H2B 0.8501 . ?
O2 H2C 0.8500 . ?

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 Cu1 N1 93.58(14) . . ?
O1 Cu1 O3 166.14(14) . . ?
N1 Cu1 O3 84.45(14) . . ?
O1 Cu1 O2 91.29(14) . . ?
N1 Cu1 O2 166.59(15) . . ?
O3 Cu1 O2 87.84(14) . . ?
O1 Cu1 O4 94.63(13) . 4_545 ?
N1 Cu1 O4 106.29(14) . 4_545 ?
O3 Cu1 O4 99.10(14) . 4_545 ?
O2 Cu1 O4 85.73(16) . 4_545 ?
C5 O1 Cu1 126.8(2) . . ?
C9 O3 Cu1 115.4(3) . . ?
C9 O4 Cu1 122.8(3) . 4 ?
C7 N1 C8 120.6(4) . . ?
C7 N1 Cu1 126.8(3) . . ?
C8 N1 Cu1 112.1(3) . . ?
H5C O5 H5D 108.0 . . ?
H5C O5 H5C 103.6 . 2_755 ?
H5D O5 H5C 146.9 . 2_755 ?
H5C O5 H5D 146.9 . 2_755 ?
H5D O5 H5D 43.7 . 2_755 ?
H5C O5 H5D 108.0 2_755 2_755 ?
C3 C6 C5 119.4(4) . . ?
C3 C6 C7 117.6(4) . . ?
C5 C6 C7 123.0(4) . . ?
C2 C3 C6 122.4(4) . . ?
C2 C3 H3 118.8 . . ?
C6 C3 H3 118.8 . . ?
N1 C7 C6 124.9(4) . . ?
N1 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
O4 C9 O3 125.3(4) . . ?
O4 C9 C8 117.9(4) . . ?
O3 C9 C8 116.8(4) . . ?
F1 C1 C2 118.2(4) . . ?
F1 C1 C4 118.2(4) . . ?
C2 C1 C4 123.6(4) . . ?
O1 C5 C4 118.1(4) . . ?
O1 C5 C6 124.4(3) . . ?
C4 C5 C6 117.5(4) . . ?
N1 C8 C9 108.9(3) . . ?
N1 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
N1 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C1 C4 C5 120.3(4) . . ?
C1 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C1 C2 C3 116.8(4) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
Cu1 O2 H2B 109.8 . . ?
Cu1 O2 H2C 109.7 . . ?
H2B O2 H2C 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C6 C3 C2 -0.8(6) . . . . ?
C7 C6 C3 C2 176.9(4) . . . . ?
C8 N1 C7 C6 -179.9(4) . . . . ?
Cu1 N1 C7 C6 -8.2(6) . . . . ?
C3 C6 C7 N1 -175.6(4) . . . . ?
C5 C6 C7 N1 2.0(6) . . . . ?
Cu1 O4 C9 O3 -25.7(6) 4 . . . ?
Cu1 O4 C9 C8 155.9(3) 4 . . . ?
Cu1 O3 C9 O4 178.4(4) . . . . ?
Cu1 O3 C9 C8 -3.2(5) . . . . ?
Cu1 O1 C5 C4 176.3(3) . . . . ?
Cu1 O1 C5 C6 -5.2(6) . . . . ?
C3 C6 C5 O1 -177.3(4) . . . . ?
C7 C6 C5 O1 5.2(6) . . . . ?
C3 C6 C5 C4 1.1(6) . . . . ?
C7 C6 C5 C4 -176.4(4) . . . . ?
C7 N1 C8 C9 156.2(4) . . . . ?
Cu1 N1 C8 C9 -16.6(4) . . . . ?
O4 C9 C8 N1 -168.4(4) . . . . ?
O3 C9 C8 N1 13.1(5) . . . . ?
F1 C1 C4 C5 177.5(4) . . . . ?
C2 C1 C4 C5 -1.1(7) . . . . ?
O1 C5 C4 C1 178.3(4) . . . . ?
C6 C5 C4 C1 -0.2(6) . . . . ?
F1 C1 C2 C3 -177.1(4) . . . . ?
C4 C1 C2 C3 1.5(7) . . . . ?
C6 C3 C2 C1 -0.6(6) . . . . ?

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
_geom_hbond_publ_flag
O5 H5C O4 0.85 2.15 2.987(5) 167.2 2_655 yes
O5 H5D O2 0.85 2.22 3.059(6) 167.4 3_545 yes
O5 H5D O2 0.85 2.63 3.059(6) 112.8 4_645 yes
C4 H4 O4 0.93 2.57 3.444(6) 156.4 3_545 yes
C2 H2 O3 0.93 2.64 3.471(5) 148.6 8_556 yes
O2 H2B O1 0.85 1.82 2.650(5) 165.1 2_655 yes
O2 H2C O5 0.85 2.21 3.059(6) 177.4 3_455 yes

_refine_diff_density_max         0.952
_refine_diff_density_min         -1.969
_refine_diff_density_rms         0.148

####################################################################### 
# 
# 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_1_a_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1978227'
loop_
_audit_author_name
_audit_author_address
'Hao Su'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2021-12-07 deposited with the CCDC.	2022-02-08 downloaded from the CCDC.
;
_audit_creation_date             2021-12-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 Cu2 F2 N2 O6, H2 O'
_chemical_formula_sum            'C18 H14 Cu2 F2 N2 O7'
_chemical_formula_weight         535.39
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.6777(4)
_cell_length_b                   8.5198(5)
_cell_length_c                   33.3475(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1897.23(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6769
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.64
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   0.619
_shelx_estimated_absorpt_T_min   0.490
_exptl_absorpt_coefficient_mu    2.308
_exptl_absorpt_correction_T_max  0.619
_exptl_absorpt_correction_T_min  0.491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.36
_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  0.0386
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            25073
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.232
_diffrn_reflns_theta_min         1.221
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4474
_reflns_number_total             5154
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.368(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5154
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.097
_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)+(0.0324P)²+1.1511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0810
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.632(19)
 0.368(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.006
4.a Free rotating group:
 O7(H7A,H7B)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C17(H17A,H17B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.86521(8) 1.03404(7) 0.68647(2) 0.03393(14) Uani 1 1 d . . . . .
Cu2 Cu 0.14627(8) 0.67371(6) 0.67968(2) 0.02812(12) Uani 1 1 d . . . . .
F1 F 1.1073(7) 0.8157(5) 0.50746(10) 0.0956(14) Uani 1 1 d . . . . .
F2 F -0.2696(6) 0.2302(5) 0.54761(10) 0.0752(12) Uani 1 1 d . . . . .
O1 O 0.8577(6) 0.9723(5) 0.63209(10) 0.0541(9) Uani 1 1 d . U . . .
O2 O 0.9029(4) 1.0806(3) 0.74362(9) 0.0324(7) Uani 1 1 d . . . . .
O3 O 1.0772(4) 1.2284(4) 0.78500(8) 0.0300(7) Uani 1 1 d . . . . .
O4 O 0.5938(4) 0.9623(4) 0.69932(9) 0.0354(7) Uani 1 1 d . . . . .
O5 O 0.3200(4) 0.8241(4) 0.70661(9) 0.0366(7) Uani 1 1 d . . . . .
O6 O -0.0158(4) 0.5235(4) 0.65381(9) 0.0379(7) Uani 1 1 d . . . . .
N1 N 0.3615(5) 0.6565(4) 0.64220(10) 0.0315(7) Uani 1 1 d . . . . .
N2 N 1.1230(5) 1.1360(4) 0.68088(10) 0.0286(7) Uani 1 1 d . . . . .
C1 C 1.1369(11) 0.8900(7) 0.54331(15) 0.0613(16) Uani 1 1 d . . . . .
C2 C 1.3202(10) 0.9568(7) 0.54962(16) 0.0579(15) Uani 1 1 d . . . . .
H2 H 1.422167 0.949813 0.530705 0.069 Uiso 1 1 calc R U . . .
C3 C 0.9828(9) 0.8944(7) 0.56956(16) 0.0549(15) Uani 1 1 d . . . . .
H3 H 0.861102 0.847455 0.563191 0.066 Uiso 1 1 calc R U . . .
C4 C 1.0087(8) 0.9719(7) 0.60718(14) 0.0436(12) Uani 1 1 d . . . . .
C5 C 1.1954(6) 1.0450(6) 0.61408(13) 0.0331(10) Uani 1 1 d . . . . .
C6 C 1.3464(8) 1.0347(6) 0.58520(14) 0.0447(11) Uani 1 1 d . . . . .
H6 H 1.469007 1.082472 0.590291 0.054 Uiso 1 1 calc R U . . .
C7 C 1.2389(6) 1.1279(5) 0.65069(13) 0.0303(9) Uani 1 1 d . . . . .
H7 H 1.361324 1.179471 0.652402 0.036 Uiso 1 1 calc R U . . .
C8 C 1.1886(6) 1.2137(5) 0.71773(13) 0.0321(10) Uani 1 1 d . . . . .
H8A H 1.189928 1.326512 0.713866 0.038 Uiso 1 1 calc R U . . .
H8B H 1.323230 1.180180 0.724492 0.038 Uiso 1 1 calc R U . . .
C9 C 1.0472(6) 1.1717(5) 0.75114(12) 0.0265(8) Uani 1 1 d . . . . .
C10 C -0.1187(8) 0.3189(6) 0.56295(14) 0.0466(12) Uani 1 1 d . . . . .
C11 C 0.0487(9) 0.3411(7) 0.53957(15) 0.0517(14) Uani 1 1 d . . . . .
H11 H 0.058834 0.297609 0.514069 0.062 Uiso 1 1 calc R U . . .
C12 C 0.1983(8) 0.4290(6) 0.55538(15) 0.0452(13) Uani 1 1 d . . . . .
H12 H 0.312654 0.446629 0.540119 0.054 Uiso 1 1 calc R U . . .
C13 C -0.1407(8) 0.3782(6) 0.60050(13) 0.0401(10) Uani 1 1 d . . . . .
H13 H -0.256948 0.357945 0.614947 0.048 Uiso 1 1 calc R U . . .
C14 C 0.0111(6) 0.4698(5) 0.61749(13) 0.0316(9) Uani 1 1 d . . . . .
C15 C 0.1868(6) 0.4952(5) 0.59433(13) 0.0328(10) Uani 1 1 d . . . . .
C16 C 0.3527(7) 0.5872(5) 0.60838(13) 0.0352(9) Uani 1 1 d . . . . .
H16 H 0.462601 0.596976 0.591435 0.042 Uiso 1 1 calc R U . . .
C17 C 0.5371(6) 0.7484(6) 0.65331(15) 0.0364(10) Uani 1 1 d . . . . .
H17A H 0.580038 0.812021 0.630761 0.044 Uiso 1 1 calc R U . . .
H17B H 0.646207 0.678999 0.660655 0.044 Uiso 1 1 calc R U . . .
C18 C 0.4831(6) 0.8538(5) 0.68869(14) 0.0298(9) Uani 1 1 d . . . . .
O7 O 0.6863(8) 1.3382(6) 0.69522(17) 0.0837(15) Uani 1 1 d G . . . .
H7A H 0.785568 1.396988 0.690202 0.126 Uiso 1 1 d G U . . .
H7B H 0.606925 1.396149 0.708680 0.126 Uiso 1 1 d G 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
Cu1 O1 1.889(3) . ?
Cu1 O2 1.963(3) . ?
Cu1 O4 1.960(3) . ?
Cu1 N2 1.937(3) . ?
Cu2 O3 1.957(3) 3_646 ?
Cu2 O5 1.948(3) . ?
Cu2 O6 1.885(3) . ?
Cu2 N1 1.910(3) . ?
F1 C1 1.367(6) . ?
F2 C10 1.360(6) . ?
O1 C4 1.307(6) . ?
O2 C9 1.263(5) . ?
O3 C9 1.244(5) . ?
O4 C18 1.236(5) . ?
O5 C18 1.268(5) . ?
O6 C14 1.307(5) . ?
N1 C16 1.275(5) . ?
N1 C17 1.458(6) . ?
N2 C7 1.272(5) . ?
N2 C8 1.463(5) . ?
C1 C2 1.366(9) . ?
C1 C3 1.352(8) . ?
C2 H2 0.9300 . ?
C2 C6 1.371(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.429(7) . ?
C4 C5 1.412(7) . ?
C5 C6 1.397(6) . ?
C5 C7 1.440(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.503(6) . ?
C10 C11 1.376(7) . ?
C10 C13 1.358(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.355(8) . ?
C12 H12 0.9300 . ?
C12 C15 1.418(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.399(6) . ?
C14 C15 1.422(6) . ?
C15 C16 1.435(6) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.525(6) . ?
O7 H7A 0.8479 . ?
O7 H7B 0.8521 . ?

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 Cu1 O2 172.67(17) . . ?
O1 Cu1 O4 95.64(15) . . ?
O1 Cu1 N2 93.22(15) . . ?
O4 Cu1 O2 88.24(12) . . ?
N2 Cu1 O2 83.63(13) . . ?
N2 Cu1 O4 169.29(14) . . ?
O5 Cu2 O3 91.15(13) . 3_646 ?
O6 Cu2 O3 89.96(13) . 3_646 ?
O6 Cu2 O5 178.27(15) . . ?
O6 Cu2 N1 94.62(14) . . ?
N1 Cu2 O3 170.24(14) . 3_646 ?
N1 Cu2 O5 84.48(14) . . ?
C4 O1 Cu1 126.2(3) . . ?
C9 O2 Cu1 114.5(2) . . ?
C9 O3 Cu2 109.3(3) . 3_656 ?
C18 O4 Cu1 136.4(3) . . ?
C18 O5 Cu2 115.2(3) . . ?
C14 O6 Cu2 125.7(3) . . ?
C16 N1 Cu2 125.4(3) . . ?
C16 N1 C17 120.7(4) . . ?
C17 N1 Cu2 113.4(3) . . ?
C7 N2 Cu1 126.4(3) . . ?
C7 N2 C8 120.5(4) . . ?
C8 N2 Cu1 112.8(2) . . ?
C2 C1 F1 117.2(6) . . ?
C3 C1 F1 118.0(6) . . ?
C3 C1 C2 124.8(5) . . ?
C1 C2 H2 121.6 . . ?
C1 C2 C6 116.7(5) . . ?
C6 C2 H2 121.6 . . ?
C1 C3 H3 120.4 . . ?
C1 C3 C4 119.3(5) . . ?
C4 C3 H3 120.4 . . ?
O1 C4 C3 117.8(5) . . ?
O1 C4 C5 125.2(4) . . ?
C5 C4 C3 117.0(5) . . ?
C4 C5 C7 122.1(4) . . ?
C6 C5 C4 119.8(4) . . ?
C6 C5 C7 118.0(4) . . ?
C2 C6 C5 122.4(5) . . ?
C2 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
N2 C7 C5 125.1(4) . . ?
N2 C7 H7 117.4 . . ?
C5 C7 H7 117.4 . . ?
N2 C8 H8A 109.9 . . ?
N2 C8 H8B 109.9 . . ?
N2 C8 C9 109.1(3) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
O2 C9 C8 118.6(4) . . ?
O3 C9 O2 122.8(4) . . ?
O3 C9 C8 118.7(4) . . ?
F2 C10 C11 117.7(4) . . ?
C13 C10 F2 118.3(5) . . ?
C13 C10 C11 124.0(5) . . ?
C10 C11 H11 121.5 . . ?
C12 C11 C10 117.0(5) . . ?
C12 C11 H11 121.5 . . ?
C11 C12 H12 118.8 . . ?
C11 C12 C15 122.4(5) . . ?
C15 C12 H12 118.8 . . ?
C10 C13 H13 119.9 . . ?
C10 C13 C14 120.2(5) . . ?
C14 C13 H13 119.9 . . ?
O6 C14 C13 118.1(4) . . ?
O6 C14 C15 124.3(4) . . ?
C13 C14 C15 117.6(4) . . ?
C12 C15 C14 118.8(4) . . ?
C12 C15 C16 118.3(4) . . ?
C14 C15 C16 122.9(4) . . ?
N1 C16 C15 125.3(4) . . ?
N1 C16 H16 117.4 . . ?
C15 C16 H16 117.4 . . ?
N1 C17 H17A 109.9 . . ?
N1 C17 H17B 109.9 . . ?
N1 C17 C18 108.8(3) . . ?
H17A C17 H17B 108.3 . . ?
C18 C17 H17A 109.9 . . ?
C18 C17 H17B 109.9 . . ?
O4 C18 O5 121.8(4) . . ?
O4 C18 C17 121.4(4) . . ?
O5 C18 C17 116.8(4) . . ?
H7A O7 H7B 104.3 . . ?

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
Cu1 O1 C4 C3 168.7(4) . . . . ?
Cu1 O1 C4 C5 -12.7(8) . . . . ?
Cu1 O2 C9 O3 171.0(3) . . . . ?
Cu1 O2 C9 C8 -8.9(5) . . . . ?
Cu1 O4 C18 O5 170.2(3) . . . . ?
Cu1 O4 C18 C17 -9.6(7) . . . . ?
Cu1 N2 C7 C5 2.5(6) . . . . ?
Cu1 N2 C8 C9 7.9(4) . . . . ?
Cu2 O3 C9 O2 -6.6(5) 3_656 . . . ?
Cu2 O3 C9 C8 173.3(3) 3_656 . . . ?
Cu2 O5 C18 O4 169.7(3) . . . . ?
Cu2 O5 C18 C17 -10.5(5) . . . . ?
Cu2 O6 C14 C13 -169.8(3) . . . . ?
Cu2 O6 C14 C15 11.7(6) . . . . ?
Cu2 N1 C16 C15 -7.2(7) . . . . ?
Cu2 N1 C17 C18 -9.3(5) . . . . ?
F1 C1 C2 C6 178.2(5) . . . . ?
F1 C1 C3 C4 -179.7(5) . . . . ?
F2 C10 C11 C12 -179.7(5) . . . . ?
F2 C10 C13 C14 179.8(5) . . . . ?
O1 C4 C5 C6 179.3(5) . . . . ?
O1 C4 C5 C7 0.8(8) . . . . ?
O3 Cu2 O6 C14 156.7(4) 3_646 . . . ?
O4 Cu1 O1 C4 -171.3(5) . . . . ?
O6 C14 C15 C12 179.3(5) . . . . ?
O6 C14 C15 C16 -1.7(7) . . . . ?
N1 Cu2 O6 C14 -14.7(4) . . . . ?
N1 C17 C18 O4 -167.2(4) . . . . ?
N1 C17 C18 O5 13.0(6) . . . . ?
N2 Cu1 O1 C4 14.7(5) . . . . ?
N2 C8 C9 O2 0.7(5) . . . . ?
N2 C8 C9 O3 -179.2(4) . . . . ?
C1 C2 C6 C5 0.6(9) . . . . ?
C1 C3 C4 O1 -179.1(6) . . . . ?
C1 C3 C4 C5 2.1(9) . . . . ?
C2 C1 C3 C4 -0.9(11) . . . . ?
C3 C1 C2 C6 -0.6(10) . . . . ?
C3 C4 C5 C6 -2.1(8) . . . . ?
C3 C4 C5 C7 179.5(5) . . . . ?
C4 C5 C6 C2 0.7(8) . . . . ?
C4 C5 C7 N2 4.5(7) . . . . ?
C6 C5 C7 N2 -174.0(4) . . . . ?
C7 N2 C8 C9 -165.9(4) . . . . ?
C7 C5 C6 C2 179.2(5) . . . . ?
C8 N2 C7 C5 175.4(4) . . . . ?
C10 C11 C12 C15 0.6(9) . . . . ?
C10 C13 C14 O6 -179.5(5) . . . . ?
C10 C13 C14 C15 -0.9(7) . . . . ?
C11 C10 C13 C14 0.9(9) . . . . ?
C11 C12 C15 C14 -0.7(8) . . . . ?
C11 C12 C15 C16 -179.8(5) . . . . ?
C12 C15 C16 N1 178.3(5) . . . . ?
C13 C10 C11 C12 -0.7(9) . . . . ?
C13 C14 C15 C12 0.8(7) . . . . ?
C13 C14 C15 C16 179.9(4) . . . . ?
C14 C15 C16 N1 -0.7(8) . . . . ?
C16 N1 C17 C18 163.8(4) . . . . ?
C17 N1 C16 C15 -179.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.632(19)
2 0.368(19)

