# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1523440'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2016-12-21 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         ?
_chemical_formula_sum            'C8 H7 Cu F2 N3 O3'
_chemical_formula_weight         294.71

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           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.7839(16)
_cell_length_b                   6.5316(13)
_cell_length_c                   10.911(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.846(7)
_cell_angle_gamma                90
_cell_volume                     536.22(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3540
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      26.84

_exptl_crystal_description       strip
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_F_000             294
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.076
_exptl_absorpt_coefficient_mu    2.065
_shelx_estimated_absorpt_T_min   0.586
_shelx_estimated_absorpt_T_max   0.859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5070
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7543
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0947
_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       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.669
_diffrn_reflns_theta_max         26.016
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1156
_reflns_number_gt                923
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0581P)²+0.0555P] 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         1156
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.0983
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 0.5000 0.5000 0.5000 0.0308(2) Uani 1 2 d S . P . .
F1 F -0.0854(4) 0.2500 0.2950(3) 0.0741(9) Uani 1 2 d S T P . .
F2 F 0.3296(4) 0.2500 0.0548(3) 0.0674(8) Uani 1 2 d S T P . .
O1 O 0.3262(3) 0.4221(3) 0.34288(17) 0.0417(5) Uani 1 1 d . . . . .
O2 O 0.3322(4) 0.2500 0.6075(3) 0.0483(8) Uani 1 2 d S T P . .
H2 H 0.2287 0.2857 0.5786 0.072 Uiso 0.5 1 calc R U P . .
N1 N 0.6431(4) 0.2500 0.4928(3) 0.0305(7) Uani 1 2 d S T P . .
N2 N 0.8025(4) 0.2500 0.5440(3) 0.0361(8) Uani 1 2 d S T P . .
N3 N 0.9501(5) 0.2500 0.5882(4) 0.0627(12) Uani 1 2 d S T P . .
C1 C 0.2739(5) 0.2500 0.2992(3) 0.0291(8) Uani 1 2 d S T P . .
C2 C 0.1250(5) 0.2500 0.1787(3) 0.0298(8) Uani 1 2 d S T P . .
C3 C -0.0492(6) 0.2500 0.1800(4) 0.0437(10) Uani 1 2 d S T P . .
C4 C -0.1872(6) 0.2500 0.0701(5) 0.0592(14) Uani 1 2 d S T P . .
H4 H -0.3053 0.2500 0.0736 0.071 Uiso 1 2 calc R U P . .
C5 C -0.1431(8) 0.2500 -0.0431(5) 0.0594(15) Uani 1 2 d S T P . .
H5 H -0.2335 0.2500 -0.1178 0.071 Uiso 1 2 calc R U P . .
C6 C 0.0284(7) 0.2500 -0.0503(5) 0.0529(12) Uani 1 2 d S T P . .
H6 H 0.0562 0.2500 -0.1282 0.064 Uiso 1 2 calc R U P . .
C7 C 0.1587(6) 0.2500 0.0604(4) 0.0382(10) Uani 1 2 d S T P . .
C8 C 0.3721(7) 0.2500 0.7402(5) 0.0769(18) Uani 1 2 d S T P . .
H8A H 0.2843 0.3283 0.7675 0.115 Uiso 0.5 1 calc R U P . .
H8B H 0.4872 0.3099 0.7738 0.115 Uiso 0.5 1 calc R U P . .
H8C H 0.3722 0.1118 0.7702 0.115 Uiso 0.5 1 calc R U P . .


_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 1.9595(18) . ?
Cu1 O1 1.9595(18) 3_666 ?
Cu1 N1 1.9894(17) . ?
Cu1 N1 1.9894(17) 3_666 ?
F1 C3 1.354(5) . ?
F2 C7 1.347(5) . ?
O1 C1 1.248(2) . ?
O2 C8 1.401(5) . ?
O2 H2 0.8200 . ?
N1 N2 1.223(4) . ?
N1 Cu1 1.9894(17) 2_646 ?
N2 N3 1.127(4) . ?
C1 O1 1.248(2) 4_565 ?
C1 C2 1.514(5) . ?
C2 C3 1.360(6) . ?
C2 C7 1.381(6) . ?
C3 C4 1.390(6) . ?
C4 C5 1.364(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.358(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.364(6) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
O1 Cu1 O1 180.00(8) . 3_666 ?
O1 Cu1 N1 91.16(10) . . ?
O1 Cu1 N1 88.84(10) 3_666 . ?
O1 Cu1 N1 88.84(10) . 3_666 ?
O1 Cu1 N1 91.16(10) 3_666 3_666 ?
N1 Cu1 N1 180.00(14) . 3_666 ?
C1 O1 Cu1 130.76(19) . . ?
C8 O2 H2 109.5 . . ?
N2 N1 Cu1 119.66(11) . 2_646 ?
N2 N1 Cu1 119.66(11) . . ?
Cu1 N1 Cu1 110.33(14) 2_646 . ?
N3 N2 N1 178.3(4) . . ?
O1 C1 O1 128.5(3) 4_565 . ?
O1 C1 C2 115.74(16) 4_565 . ?
O1 C1 C2 115.74(16) . . ?
C3 C2 C7 116.0(4) . . ?
C3 C2 C1 122.3(3) . . ?
C7 C2 C1 121.7(4) . . ?
F1 C3 C2 117.0(4) . . ?
F1 C3 C4 120.1(4) . . ?
C2 C3 C4 122.9(4) . . ?
C5 C4 C3 117.6(5) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
C6 C5 C4 122.1(4) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 117.9(5) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
F2 C7 C6 118.6(4) . . ?
F2 C7 C2 117.9(4) . . ?
C6 C7 C2 123.5(4) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
Cu1 O1 C1 O1 -3.7(6) . . . 4_565 ?
Cu1 O1 C1 C2 175.1(2) . . . . ?
O1 C1 C2 C3 89.5(3) 4_565 . . . ?
O1 C1 C2 C3 -89.5(3) . . . . ?
O1 C1 C2 C7 -90.5(3) 4_565 . . . ?
O1 C1 C2 C7 90.5(3) . . . . ?
C7 C2 C3 F1 180.000(0) . . . . ?
C1 C2 C3 F1 0.000(1) . . . . ?
C7 C2 C3 C4 0.000(0) . . . . ?
C1 C2 C3 C4 180.000(0) . . . . ?
F1 C3 C4 C5 180.000(1) . . . . ?
C2 C3 C4 C5 0.000(0) . . . . ?
C3 C4 C5 C6 0.000(0) . . . . ?
C4 C5 C6 C7 0.000(0) . . . . ?
C5 C6 C7 F2 180.0 . . . . ?
C5 C6 C7 C2 0.000(0) . . . . ?
C3 C2 C7 F2 180.000(0) . . . . ?
C1 C2 C7 F2 0.000(0) . . . . ?
C3 C2 C7 C6 0.000(0) . . . . ?
C1 C2 C7 C6 180.000(0) . . . . ?

_refine_diff_density_max         0.482
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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 1523439'
_audit_update_record             
;
2016-12-21 deposited with the CCDC.
2016-12-21 downloaded from the CCDC.
;
_audit_creation_date             2016-12-20
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2016.11.22 svn.r3360 for OlexSys, GUI svn.r3563)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H4 Cu F N3 O2, C H4 O'
_chemical_formula_sum            'C8 H8 Cu F N3 O3'
_chemical_formula_weight         276.71
_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                   6.410(3)
_cell_length_b                   7.512(3)
_cell_length_c                   22.879(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1101.7(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5299
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.580
_cell_measurement_theta_min      2.854
_shelx_estimated_absorpt_T_max   0.741
_shelx_estimated_absorpt_T_min   0.716
_exptl_absorpt_coefficient_mu    1.991
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       strip
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10760
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.696
_diffrn_reflns_theta_min         2.854
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2249
_reflns_number_total             2576
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.400
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.45(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     114
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0248
_refine_ls_restrained_S_all      1.055
_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)+(0.0318P)²+0.4669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0663
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.55(3) 0.45(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F1') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C3, Cu1, O2, N1, C1, N2, C2, O0AA, N3, C7, F1, C4, F1', C6, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: H3(0.15) H7(0.85) F1(0.85) F1'(0.15)
6.a Riding coordinates:
 O3(H3A)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
6.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.11023(4) 0.25163(4) -0.00129(2) 0.02582(11) Uani 1 1 d . U . . .
N1 N 0.3601(4) 0.4034(3) 0.01358(12) 0.0301(5) Uani 1 1 d . U . . .
N2 N 0.3624(4) 0.5578(3) -0.00086(13) 0.0398(6) Uani 1 1 d . U . . .
N3 N 0.3644(6) 0.7039(4) -0.0131(2) 0.0776(13) Uani 1 1 d . U . . .
C1 C -0.1433(5) 0.4416(4) -0.08663(12) 0.0282(6) Uani 1 1 d . U . . .
C2 C -0.1505(6) 0.5581(4) -0.14027(13) 0.0329(6) Uani 1 1 d . U . . .
C3 C -0.3244(7) 0.5694(6) -0.17670(16) 0.0508(9) Uani 1 1 d . U . . .
H3 H -0.4408 0.5005 -0.1679 0.061 Uiso 0.15 1 calc R . P A 2
C4 C -0.3311(8) 0.6779(6) -0.22489(18) 0.0634(12) Uani 1 1 d . U . . .
H4 H -0.4503 0.6813 -0.2481 0.076 Uiso 1 1 calc R . . . .
C5 C -0.1652(10) 0.7793(7) -0.2386(2) 0.0791(14) Uani 1 1 d . U . . .
H5 H -0.1709 0.8566 -0.2703 0.095 Uiso 1 1 calc R . . . .
C6 C 0.0120(10) 0.7676(8) -0.2055(2) 0.0900(19) Uani 1 1 d . U . . .
H6 H 0.1295 0.8331 -0.2157 0.108 Uiso 1 1 calc R . . . .
C7 C 0.0165(7) 0.6586(7) -0.1568(2) 0.0681(14) Uani 1 1 d . U . . .
H7 H 0.1378 0.6536 -0.1346 0.082 Uiso 0.85 1 calc R . P B 1
O0AA O -0.3147(3) 0.3995(3) -0.06477(10) 0.0358(5) Uani 1 1 d . U . . .
O2 O 0.0351(3) 0.3999(3) -0.06855(10) 0.0366(5) Uani 1 1 d . U . . .
O3 O -0.1292(4) 0.4386(3) 0.05666(10) 0.0442(6) Uani 1 1 d . . . . .
H3A H -0.1301 0.5572 0.0410 0.053 Uiso 1 1 d R . . . .
F1 F -0.4906(5) 0.4685(6) -0.16722(15) 0.1010(14) Uani 0.85 1 d . U P C 1
C8 C -0.1008(13) 0.4431(8) 0.1174(2) 0.116(3) Uani 1 1 d . . . . .
H8A H 0.0281 0.5022 0.1263 0.174 Uiso 1 1 calc GR . . . .
H8B H -0.0967 0.3237 0.1323 0.174 Uiso 1 1 calc GR . . . .
H8C H -0.2144 0.5064 0.1351 0.174 Uiso 1 1 calc GR . . . .
F1' F 0.179(4) 0.665(4) -0.1321(10) 0.110(8) Uani 0.15 1 d . U P D 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
Cu1 N1 1.995(2) . ?
Cu1 N1 2.001(2) 4_455 ?
Cu1 O0AA 1.951(2) 4 ?
Cu1 O2 1.960(2) . ?
N1 Cu1 2.001(2) 4 ?
N1 N2 1.206(3) . ?
N2 N3 1.133(4) . ?
C1 C2 1.508(4) . ?
C1 O0AA 1.248(4) . ?
C1 O2 1.256(4) . ?
C2 C3 1.395(5) . ?
C2 C7 1.363(5) . ?
C3 C4 1.372(5) . ?
C3 F1 1.325(5) . ?
C4 C5 1.345(7) . ?
C5 C6 1.368(8) . ?
C6 C7 1.383(6) . ?
C7 F1' 1.19(2) . ?
O0AA Cu1 1.951(2) 4_455 ?
O3 C8 1.401(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
N1 Cu1 N1 178.17(2) . 4_455 ?
O0AA Cu1 N1 90.14(10) 4 . ?
O0AA Cu1 N1 88.15(10) 4 4_455 ?
O0AA Cu1 O2 179.02(10) 4 . ?
O2 Cu1 N1 91.36(10) . 4_455 ?
O2 Cu1 N1 90.36(9) . . ?
Cu1 N1 Cu1 106.67(11) . 4 ?
N2 N1 Cu1 120.8(2) . . ?
N2 N1 Cu1 120.7(2) . 4 ?
N3 N2 N1 178.4(4) . . ?
O0AA C1 C2 116.5(3) . . ?
O0AA C1 O2 127.4(3) . . ?
O2 C1 C2 116.1(3) . . ?
C3 C2 C1 123.1(3) . . ?
C7 C2 C1 121.6(3) . . ?
C7 C2 C3 115.3(3) . . ?
C4 C3 C2 122.8(4) . . ?
F1 C3 C2 120.6(3) . . ?
F1 C3 C4 116.5(4) . . ?
C5 C4 C3 119.9(4) . . ?
C4 C5 C6 119.4(4) . . ?
C5 C6 C7 120.1(5) . . ?
C2 C7 C6 122.4(4) . . ?
F1' C7 C2 125.4(10) . . ?
F1' C7 C6 112.2(10) . . ?
C1 O0AA Cu1 132.5(2) . 4_455 ?
C1 O2 Cu1 128.60(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.55(3)
2 0.45(3)

