# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1550633'
_audit_update_record             
;
2017-05-17 deposited with the CCDC.
2017-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 Cu F N3 O3'
_chemical_formula_sum            'C10 H12 Cu F N3 O3'
_chemical_formula_weight         304.77

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      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                   7.5623(9)
_cell_length_b                   6.3355(6)
_cell_length_c                   13.6245(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.307(3)
_cell_angle_gamma                90
_cell_volume                     632.52(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1817
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      25.72

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             310
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.742
_shelx_estimated_absorpt_T_min   0.651
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6510
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4315
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.826
_diffrn_reflns_theta_max         26.358
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2340
_reflns_number_gt                1692
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    1.000

_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       APEX3
_computing_data_reduction        APEX3
_computing_structure_solution    'SHELXS-2013/1 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0128P)²+0.2950P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.30(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2340
_refine_ls_number_parameters     206
_refine_ls_number_restraints     267
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.0629
_refine_ls_wR_factor_gt          0.0566
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.002
_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
C8 C 0.2526(6) -0.124(2) 0.3460(3) 0.0187(12) Uani 1 1 d D U . . .
C9 C 0.4054(9) -0.148(2) 0.7033(4) 0.0357(18) Uani 1 1 d . . . . .
H9A H 0.5398 -0.1527 0.7288 0.043 Uiso 1 1 calc R U . . .
H9B H 0.3553 -0.2805 0.7244 0.043 Uiso 1 1 calc R U . . .
C10 C 0.3309(11) 0.0379(12) 0.7493(5) 0.051(2) Uani 1 1 d . . . . .
H10A H 0.1972 0.0347 0.7293 0.076 Uiso 1 1 calc R U . . .
H10B H 0.3745 0.1691 0.7253 0.076 Uiso 1 1 calc R U . . .
H10C H 0.3726 0.0309 0.8233 0.076 Uiso 1 1 calc R U . . .
Cu1 Cu 0.49804(18) -0.3795(6) 0.49852(9) 0.01530(17) Uani 1 1 d . . . . .
N1 N 0.6452(5) -0.1252(18) 0.4762(3) 0.0169(9) Uani 1 1 d . . . . .
N2 N 0.8093(6) -0.1323(17) 0.5041(3) 0.0256(10) Uani 1 1 d . . . . .
N3 N 0.9636(6) -0.136(3) 0.5278(5) 0.0600(19) Uani 1 1 d . . . . .
O1 O 0.3056(9) -0.3079(8) 0.3794(4) 0.021(2) Uani 1 1 d . . . . .
O2 O 0.3079(10) 0.0478(8) 0.3847(4) 0.0217(19) Uani 1 1 d . . . . .
O3 O 0.3589(4) -0.1357(15) 0.5947(3) 0.0200(8) Uani 1 1 d D . . . .
H3A H 0.254(4) -0.153(13) 0.579(4) 0.024 Uiso 1 1 d D U . . .
C1 C 0.246(2) 0.267(3) 0.0294(12) 0.030(3) Uani 0.61(4) 1 d D U P A 1
C2 C 0.322(2) 0.073(3) 0.0508(11) 0.027(3) Uani 0.61(4) 1 d D U P A 1
H2 H 0.4111 0.0234 0.0177 0.033 Uiso 0.61(4) 1 calc R U P A 1
C3 C 0.268(2) -0.051(2) 0.1227(11) 0.026(3) Uani 0.61(4) 1 d D U P A 1
H3 H 0.3173 -0.1888 0.1365 0.031 Uiso 0.61(4) 1 calc R U P A 1
C4 C 0.144(4) 0.021(3) 0.1746(19) 0.023(2) Uani 0.61(4) 1 d D U P A 1
C5 C 0.074(6) 0.220(5) 0.151(4) 0.025(3) Uani 0.61(4) 1 d D U P A 1
H5 H -0.0107 0.2736 0.1856 0.030 Uiso 0.61(4) 1 calc R U P A 1
C6 C 0.124(3) 0.348(3) 0.0781(15) 0.029(3) Uani 0.61(4) 1 d D U P A 1
H6 H 0.0740 0.4849 0.0632 0.035 Uiso 0.61(4) 1 calc R U P A 1
F1 F 0.292(2) 0.387(4) -0.0430(11) 0.048(3) Uani 0.61(4) 1 d D U P A 1
C7 C 0.0908(18) -0.115(3) 0.2537(10) 0.018(3) Uani 0.61(4) 1 d D U P A 1
H7A H 0.0590 -0.2587 0.2267 0.021 Uiso 0.61(4) 1 calc R U P A 1
H7B H -0.0167 -0.0539 0.2726 0.021 Uiso 0.61(4) 1 calc R U P A 1
C1' C 0.232(3) 0.330(4) 0.0380(17) 0.027(3) Uiso 0.39(4) 1 d D U P A 2
C2' C 0.331(3) 0.147(4) 0.0489(19) 0.029(3) Uiso 0.39(4) 1 d D U P A 2
H2' H 0.4207 0.1248 0.0122 0.035 Uiso 0.39(4) 1 calc R U P A 2
C3' C 0.296(4) -0.005(4) 0.1155(19) 0.023(4) Uiso 0.39(4) 1 d D U P A 2
H3' H 0.3640 -0.1326 0.1259 0.028 Uiso 0.39(4) 1 calc R U P A 2
C4' C 0.161(5) 0.030(5) 0.166(3) 0.020(3) Uiso 0.39(4) 1 d D U P A 2
C5' C 0.065(10) 0.216(7) 0.152(6) 0.023(4) Uiso 0.39(4) 1 d D U P A 2
H5' H -0.0264 0.2405 0.1877 0.028 Uiso 0.39(4) 1 calc R U P A 2
C6' C 0.097(4) 0.372(5) 0.085(2) 0.027(3) Uiso 0.39(4) 1 d D U P A 2
H6' H 0.0292 0.4991 0.0739 0.033 Uiso 0.39(4) 1 calc R U P A 2
F1' F 0.269(3) 0.473(4) -0.0290(18) 0.040(5) Uani 0.39(4) 1 d D U P A 2
C7' C 0.124(3) -0.136(5) 0.2389(13) 0.019(4) Uiso 0.39(4) 1 d D U P A 2
H7'1 H 0.1353 -0.2774 0.2103 0.023 Uiso 0.39(4) 1 calc R U P A 2
H7'2 H -0.0037 -0.1204 0.2445 0.023 Uiso 0.39(4) 1 calc R U P A 2


_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
C8 O2 1.236(11) . ?
C8 O1 1.280(11) . ?
C8 C7 1.524(10) . ?
C8 C7' 1.543(16) . ?
C9 O3 1.436(6) . ?
C9 C10 1.510(11) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
Cu1 O2 1.935(6) 2_646 ?
Cu1 O1 1.946(6) . ?
Cu1 N1 1.975(9) 2_646 ?
Cu1 N1 2.023(10) . ?
Cu1 O3 2.428(7) . ?
N1 N2 1.205(5) . ?
N1 Cu1 1.975(9) 2_656 ?
N2 N3 1.132(5) . ?
O2 Cu1 1.935(6) 2_656 ?
O3 H3A 0.78(2) . ?
C1 C2 1.355(13) . ?
C1 F1 1.360(12) . ?
C1 C6 1.365(13) . ?
C2 C3 1.397(13) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.372(12) . ?
C4 C7 1.509(14) . ?
C5 C6 1.400(14) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C1' C6' 1.354(16) . ?
C1' F1' 1.365(16) . ?
C1' C2' 1.369(17) . ?
C2' C3' 1.394(17) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.386(16) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.376(16) . ?
C4' C7' 1.516(18) . ?
C5' C6' 1.400(17) . ?
C5' H5' 0.9500 . ?
C6' H6' 0.9500 . ?
C7' H7'1 0.9900 . ?
C7' H7'2 0.9900 . ?

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
O2 C8 O1 127.4(4) . . ?
O2 C8 C7 115.9(12) . . ?
O1 C8 C7 116.4(12) . . ?
O2 C8 C7' 121.0(14) . . ?
O1 C8 C7' 111.1(14) . . ?
O3 C9 C10 111.2(8) . . ?
O3 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
O3 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 Cu1 O1 179.0(4) 2_646 . ?
O2 Cu1 N1 90.4(3) 2_646 2_646 ?
O1 Cu1 N1 90.0(2) . 2_646 ?
O2 Cu1 N1 88.8(3) 2_646 . ?
O1 Cu1 N1 90.9(2) . . ?
N1 Cu1 N1 178.6(2) 2_646 . ?
O2 Cu1 O3 92.8(2) 2_646 . ?
O1 Cu1 O3 88.1(2) . . ?
N1 Cu1 O3 94.5(3) 2_646 . ?
N1 Cu1 O3 84.4(3) . . ?
N2 N1 Cu1 122.7(9) . 2_656 ?
N2 N1 Cu1 119.0(9) . . ?
Cu1 N1 Cu1 104.83(18) 2_656 . ?
N3 N2 N1 178.1(9) . . ?
C8 O1 Cu1 127.8(5) . . ?
C8 O2 Cu1 131.9(5) . 2_656 ?
C9 O3 Cu1 119.5(6) . . ?
C9 O3 H3A 105(4) . . ?
Cu1 O3 H3A 108(6) . . ?
C2 C1 F1 119.5(11) . . ?
C2 C1 C6 122.6(12) . . ?
F1 C1 C6 117.9(11) . . ?
C1 C2 C3 118.5(11) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 121.8(11) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C5 C4 C3 116.8(12) . . ?
C5 C4 C7 122.6(11) . . ?
C3 C4 C7 120.6(11) . . ?
C4 C5 C6 122.9(15) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C1 C6 C5 117.4(14) . . ?
C1 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C4 C7 C8 108.1(14) . . ?
C4 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
C4 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C6' C1' F1' 119.5(15) . . ?
C6' C1' C2' 124.6(18) . . ?
F1' C1' C2' 115.8(14) . . ?
C1' C2' C3' 118.1(18) . . ?
C1' C2' H2' 121.0 . . ?
C3' C2' H2' 121.0 . . ?
C4' C3' C2' 119.7(17) . . ?
C4' C3' H3' 120.1 . . ?
C2' C3' H3' 120.1 . . ?
C5' C4' C3' 119.5(17) . . ?
C5' C4' C7' 120.9(15) . . ?
C3' C4' C7' 119.5(14) . . ?
C4' C5' C6' 122(2) . . ?
C4' C5' H5' 119.1 . . ?
C6' C5' H5' 119.1 . . ?
C1' C6' C5' 116(2) . . ?
C1' C6' H6' 121.8 . . ?
C5' C6' H6' 121.8 . . ?
C4' C7' C8 114(2) . . ?
C4' C7' H7'1 108.7 . . ?
C8 C7' H7'1 108.7 . . ?
C4' C7' H7'2 108.7 . . ?
C8 C7' H7'2 108.7 . . ?
H7'1 C7' H7'2 107.6 . . ?

_refine_diff_density_max         0.806
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1550632'
_audit_update_record             
;
2017-05-17 deposited with the CCDC.
2017-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H12 Cu F N3 O3'
_chemical_formula_weight         304.77

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           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                   7.6149(18)
_cell_length_b                   6.4330(15)
_cell_length_c                   13.355(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.363(3)
_cell_angle_gamma                90
_cell_volume                     645.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8424
_cell_measurement_theta_min      2.417
_cell_measurement_theta_max      25.743

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_F_000             310
_exptl_transmission_factor_min   0.6741
_exptl_transmission_factor_max   0.8344
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    1.707
_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; Bruker, 2000'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8115
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.711
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2946
_reflns_number_gt                2191
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_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 SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.09(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2946
_refine_ls_number_parameters     168
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.010
_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 0.49491(11) 0.4634(4) 0.50216(7) 0.02363(19) Uani 1 1 d . . . . .
O1 O 0.6592(6) 0.5400(8) 0.6238(4) 0.0333(13) Uani 1 1 d . . . . .
O2 O 0.6725(6) 0.8896(7) 0.6183(4) 0.0328(13) Uani 1 1 d . . . . .
O4 O 0.3390(5) 0.2151(12) 0.5943(3) 0.0369(9) Uani 1 1 d D . . . .
H4 H 0.231(2) 0.212(19) 0.578(4) 0.044 Uiso 1 1 d D U . . .
N1 N 0.3506(5) 0.7195(13) 0.5166(3) 0.0269(9) Uani 1 1 d . . . . .
N2 N 0.1929(6) 0.7267(13) 0.4891(4) 0.0422(13) Uani 1 1 d . . . . .
N3 N 0.0444(8) 0.7349(19) 0.4653(8) 0.102(3) Uani 1 1 d . . . . .
C1 C 0.7116(6) 0.7133(17) 0.6580(4) 0.0303(11) Uani 1 1 d . . . . .
C2 C 0.8433(9) 0.7126(19) 0.7573(4) 0.0484(15) Uani 1 1 d . . . . .
H2A H 0.962720 0.703305 0.741165 0.058 Uiso 1 1 calc R U . . .
H2B H 0.834072 0.844779 0.791064 0.058 Uiso 1 1 calc R U . . .
C3 C 0.8205(9) 0.5444(11) 0.8295(4) 0.0357(15) Uani 1 1 d . . . . .
C4 C 0.9410(11) 0.3824(12) 0.8485(6) 0.0518(19) Uani 1 1 d . . . . .
H4A H 1.037812 0.376701 0.814102 0.062 Uiso 1 1 calc R U . . .
C5 C 0.9192(11) 0.230(2) 0.9177(6) 0.065(2) Uani 1 1 d . . . . .
H5A H 1.002617 0.123247 0.930094 0.078 Uiso 1 1 calc R U . . .
C6 C 0.7779(13) 0.231(2) 0.9684(6) 0.072(3) Uani 1 1 d . . . . .
H6A H 0.764916 0.126876 1.014746 0.086 Uiso 1 1 calc R U . . .
C7 C 0.6561(13) 0.3868(17) 0.9507(7) 0.073(3) Uani 1 1 d . . . . .
H7A H 0.557093 0.389592 0.983325 0.087 Uiso 1 1 calc R U . . .
C8 C 0.6838(11) 0.5406(15) 0.8828(6) 0.058(2) Uani 1 1 d . . . . .
F1 F 0.5619(8) 0.6925(15) 0.8652(4) 0.115(2) Uani 1 1 d . . . . .
C9 C 0.3749(9) 0.218(2) 0.7030(5) 0.0532(16) Uani 1 1 d . . . . .
H9A H 0.328704 0.345779 0.727560 0.064 Uiso 1 1 calc R U . . .
H9B H 0.502473 0.215166 0.725873 0.064 Uiso 1 1 calc R U . . .
C10 C 0.2886(13) 0.0316(15) 0.7461(6) 0.076(3) Uani 1 1 d . . . . .
H10A H 0.322121 0.029036 0.818514 0.113 Uiso 1 1 calc R U . . .
H10B H 0.327770 -0.093950 0.717745 0.113 Uiso 1 1 calc R U . . .
H10C H 0.161464 0.042404 0.728987 0.113 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 O2 1.942(5) 2_646 ?
Cu1 O1 1.945(5) . ?
Cu1 N1 2.001(7) 2_646 ?
Cu1 N1 2.007(8) . ?
Cu1 O4 2.439(6) . ?
O1 C1 1.246(11) . ?
O2 C1 1.266(11) . ?
O4 C9 1.433(7) . ?
O4 H4 0.819(14) . ?
N1 N2 1.198(6) . ?
N2 N3 1.125(7) . ?
C1 C2 1.527(7) . ?
C2 C3 1.478(11) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.353(10) . ?
C3 C4 1.384(10) . ?
C4 C5 1.378(13) . ?
C4 H4A 0.9300 . ?
C5 C6 1.361(11) . ?
C5 H5A 0.9300 . ?
C6 C7 1.359(15) . ?
C6 H6A 0.9300 . ?
C7 C8 1.381(12) . ?
C7 H7A 0.9300 . ?
C8 F1 1.342(11) . ?
C9 C10 1.526(14) . ?
C9 H9A 0.9700 . ?
C9 H9B 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
O2 Cu1 O1 179.0(3) 2_646 . ?
O2 Cu1 N1 91.4(2) 2_646 2_646 ?
O1 Cu1 N1 89.5(2) . 2_646 ?
O2 Cu1 N1 89.1(2) 2_646 . ?
O1 Cu1 N1 90.0(2) . . ?
N1 Cu1 N1 176.3(3) 2_646 . ?
O2 Cu1 O4 87.1(2) 2_646 . ?
O1 Cu1 O4 92.55(19) . . ?
N1 Cu1 O4 83.9(3) 2_646 . ?
N1 Cu1 O4 99.8(2) . . ?
C1 O1 Cu1 131.1(5) . . ?
C1 O2 Cu1 130.0(5) . 2_656 ?
C9 O4 Cu1 118.2(6) . . ?
C9 O4 H4 106(4) . . ?
Cu1 O4 H4 116(7) . . ?
N2 N1 Cu1 120.8(7) . 2_656 ?
N2 N1 Cu1 122.6(7) . . ?
Cu1 N1 Cu1 106.81(17) 2_656 . ?
N3 N2 N1 178.5(8) . . ?
O1 C1 O2 127.5(4) . . ?
O1 C1 C2 116.2(9) . . ?
O2 C1 C2 116.3(9) . . ?
C3 C2 C1 116.0(7) . . ?
C3 C2 H2A 108.3 . . ?
C1 C2 H2A 108.3 . . ?
C3 C2 H2B 108.3 . . ?
C1 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C8 C3 C4 115.7(7) . . ?
C8 C3 C2 122.6(7) . . ?
C4 C3 C2 121.7(7) . . ?
C5 C4 C3 120.7(8) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C6 C5 C4 121.3(10) . . ?
C6 C5 H5A 119.4 . . ?
C4 C5 H5A 119.4 . . ?
C7 C6 C5 119.5(10) . . ?
C7 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
C6 C7 C8 117.9(8) . . ?
C6 C7 H7A 121.0 . . ?
C8 C7 H7A 121.0 . . ?
F1 C8 C3 117.7(8) . . ?
F1 C8 C7 117.5(8) . . ?
C3 C8 C7 124.8(8) . . ?
O4 C9 C10 110.3(8) . . ?
O4 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
O4 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_refine_diff_density_max         0.756
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.078

