# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_xb6922_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1010470'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H8 Cu F3 N3 O3'
_chemical_formula_weight         326.72

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.426(4)
_cell_length_b                   7.471(5)
_cell_length_c                   13.774(8)
_cell_angle_alpha                75.689(13)
_cell_angle_beta                 83.872(13)
_cell_angle_gamma                85.763(12)
_cell_volume                     636.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    357
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      17.44

_exptl_crystal_description       strip
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_F_000             326
_exptl_transmission_factor_min   0.5670
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.760
_shelx_estimated_absorpt_T_min   0.698
_shelx_estimated_absorpt_T_max   0.778
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3245
_diffrn_reflns_av_unetI/netI     0.1309
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.532
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2296
_reflns_number_gt                1240
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0986P)²] 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         2296
_refine_ls_number_parameters     192
_refine_ls_number_restraints     121
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.2071
_refine_ls_wR_factor_gt          0.1774
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.001

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 0.500000 0.000000 0.500000 0.0392(5) Uani 1 2 d S . P . .
Cu2 Cu 0.000000 0.000000 0.500000 0.0385(5) Uani 1 2 d S . P . .
O1 O 0.4326(9) 0.2027(8) 0.3866(4) 0.0485(16) Uani 1 1 d . . . . .
O2 O 0.0856(9) 0.1985(8) 0.3861(4) 0.0526(17) Uani 1 1 d . . . . .
O3 O 0.2146(10) 0.1445(8) 0.5999(5) 0.0552(17) Uani 1 1 d . . . . .
H3A H 0.209235 0.257512 0.580144 0.066 Uiso 1 1 calc R U . . .
C8 C 0.2911(16) 0.8108(15) -0.0245(9) 0.095(3) Uani 1 1 d D U . . .
F1 F 0.467(3) 0.803(3) -0.0822(16) 0.105(5) Uani 0.54(4) 1 d D U P A 1
F2 F 0.278(4) 0.984(2) -0.0112(19) 0.099(5) Uani 0.54(4) 1 d D U P A 1
F3 F 0.129(3) 0.805(3) -0.0769(16) 0.105(5) Uani 0.54(4) 1 d D U P A 1
F1' F 0.491(2) 0.846(4) -0.062(2) 0.096(5) Uani 0.46(4) 1 d D U P A 2
F2' F 0.207(4) 0.976(2) -0.017(2) 0.101(5) Uani 0.46(4) 1 d D U P A 2
F3' F 0.219(6) 0.738(4) -0.0942(15) 0.107(5) Uani 0.46(4) 1 d D U P A 2
N1 N 0.2652(10) -0.1443(9) 0.4775(6) 0.0426(19) Uani 1 1 d . . . . .
N2 N 0.2672(11) -0.3122(11) 0.5053(6) 0.055(2) Uani 1 1 d . . . . .
N3 N 0.2606(13) -0.4643(11) 0.5324(9) 0.092(3) Uani 1 1 d . . . . .
C1 C 0.2606(14) 0.2573(11) 0.3510(7) 0.041(2) Uani 1 1 d . . . . .
C2 C 0.2674(9) 0.4087(8) 0.2568(4) 0.044(2) Uani 1 1 d G . . . .
C3 C 0.4480(8) 0.5047(10) 0.2210(5) 0.075(4) Uani 1 1 d G . . . .
H3 H 0.564535 0.480074 0.257730 0.090 Uiso 1 1 calc R U . . .
C4 C 0.4546(9) 0.6376(10) 0.1302(5) 0.094(4) Uani 1 1 d G . . . .
H4 H 0.575468 0.701893 0.106225 0.113 Uiso 1 1 calc R U . . .
C5 C 0.2805(11) 0.6745(9) 0.0753(4) 0.064(3) Uani 1 1 d G . . . .
C6 C 0.0998(9) 0.5785(10) 0.1112(5) 0.074(3) Uani 1 1 d G . . . .
H6 H -0.016702 0.603137 0.074415 0.089 Uiso 1 1 calc R U . . .
C7 C 0.0932(7) 0.4456(9) 0.2019(5) 0.063(3) Uani 1 1 d G . . . .
H7 H -0.027639 0.381317 0.225920 0.076 Uiso 1 1 calc R U . . .
C9 C 0.189(2) 0.0953(16) 0.7048(8) 0.094(4) Uani 1 1 d . . . . .
H9A H 0.233287 0.193332 0.730504 0.141 Uiso 1 1 calc R U . . .
H9B H 0.272511 -0.015671 0.729120 0.141 Uiso 1 1 calc R U . . .
H9C H 0.044339 0.074460 0.727066 0.141 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 O1 1.949(5) . ?
Cu1 O1 1.949(5) 2_656 ?
Cu1 N1 2.010(7) . ?
Cu1 N1 2.010(7) 2_656 ?
Cu1 O3 2.515(7) . ?
Cu2 O2 1.936(6) . ?
Cu2 O2 1.936(6) 2_556 ?
Cu2 N1 1.986(6) . ?
Cu2 N1 1.986(6) 2_556 ?
Cu2 O3 2.514(6) . ?
O1 C1 1.257(9) . ?
O2 C1 1.242(10) . ?
O3 C9 1.395(11) . ?
O3 H3A 0.8200 . ?
C8 F1 1.317(12) . ?
C8 F2' 1.332(13) . ?
C8 F3 1.336(12) . ?
C8 F2 1.346(13) . ?
C8 F3' 1.352(13) . ?
C8 F1' 1.352(13) . ?
C8 C5 1.493(12) . ?
N1 N2 1.217(10) . ?
N2 N3 1.107(10) . ?
C1 C2 1.494(9) . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C6 C7 1.3900 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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 180.0 . 2_656 ?
O1 Cu1 N1 90.9(3) . . ?
O1 Cu1 N1 89.1(3) 2_656 . ?
O1 Cu1 N1 89.1(3) . 2_656 ?
O1 Cu1 N1 90.9(3) 2_656 2_656 ?
N1 Cu1 N1 180.0(4) . 2_656 ?
O1 Cu1 O3 85.6(2) . . ?
O1 Cu1 O3 94.4(2) 2_656 . ?
N1 Cu1 O3 83.3(2) . . ?
N1 Cu1 O3 96.7(2) 2_656 . ?
O2 Cu2 O2 180.0 . 2_556 ?
O2 Cu2 N1 90.5(3) . . ?
O2 Cu2 N1 89.5(3) 2_556 . ?
O2 Cu2 N1 89.5(3) . 2_556 ?
O2 Cu2 N1 90.5(3) 2_556 2_556 ?
N1 Cu2 N1 180.0 . 2_556 ?
O2 Cu2 O3 86.1(2) . . ?
O2 Cu2 O3 93.9(2) 2_556 . ?
N1 Cu2 O3 83.8(3) . . ?
N1 Cu2 O3 96.2(3) 2_556 . ?
C1 O1 Cu1 130.5(6) . . ?
C1 O2 Cu2 131.9(6) . . ?
C9 O3 Cu2 120.2(6) . . ?
C9 O3 Cu1 122.4(7) . . ?
Cu2 O3 Cu1 79.42(19) . . ?
C9 O3 H3A 109.5 . . ?
Cu2 O3 H3A 111.1 . . ?
Cu1 O3 H3A 111.2 . . ?
F1 C8 F3 109.1(11) . . ?
F1 C8 F2 104.3(11) . . ?
F3 C8 F2 104.5(11) . . ?
F2' C8 F3' 116.0(18) . . ?
F2' C8 F1' 103.7(12) . . ?
F3' C8 F1' 103.1(12) . . ?
F1 C8 C5 115.3(13) . . ?
F2' C8 C5 111.7(14) . . ?
F3 C8 C5 112.9(11) . . ?
F2 C8 C5 109.8(14) . . ?
F3' C8 C5 110.3(12) . . ?
F1' C8 C5 111.7(14) . . ?
N2 N1 Cu2 118.7(6) . . ?
N2 N1 Cu1 121.7(6) . . ?
Cu2 N1 Cu1 107.1(3) . . ?
N3 N2 N1 177.0(10) . . ?
O2 C1 O1 126.7(8) . . ?
O2 C1 C2 116.7(7) . . ?
O1 C1 C2 116.6(7) . . ?
C3 C2 C7 120.0 . . ?
C3 C2 C1 121.0(5) . . ?
C7 C2 C1 118.9(5) . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C8 120.0(6) . . ?
C4 C5 C8 119.9(6) . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
Cu2 O2 C1 O1 -3.6(15) . . . . ?
Cu2 O2 C1 C2 176.5(5) . . . . ?
Cu1 O1 C1 O2 5.2(14) . . . . ?
Cu1 O1 C1 C2 -174.9(5) . . . . ?
O2 C1 C2 C3 169.2(7) . . . . ?
O1 C1 C2 C3 -10.8(10) . . . . ?
O2 C1 C2 C7 -14.5(10) . . . . ?
O1 C1 C2 C7 165.5(6) . . . . ?
C7 C2 C3 C4 0.0 . . . . ?
C1 C2 C3 C4 176.3(7) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C3 C4 C5 C8 -177.1(8) . . . . ?
F1 C8 C5 C6 -136.1(15) . . . . ?
F2' C8 C5 C6 84.1(17) . . . . ?
F3 C8 C5 C6 -9.7(17) . . . . ?
F2 C8 C5 C6 106.5(13) . . . . ?
F3' C8 C5 C6 -46(2) . . . . ?
F1' C8 C5 C6 -160.3(15) . . . . ?
F1 C8 C5 C4 41.0(17) . . . . ?
F2' C8 C5 C4 -98.8(17) . . . . ?
F3 C8 C5 C4 167.4(16) . . . . ?
F2 C8 C5 C4 -76.4(15) . . . . ?
F3' C8 C5 C4 130.7(19) . . . . ?
F1' C8 C5 C4 16.8(18) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C8 C5 C6 C7 177.1(8) . . . . ?
C5 C6 C7 C2 0.0 . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
C1 C2 C7 C6 -176.3(7) . . . . ?

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
O3 H3A N3 0.82 2.06 2.867(10) 168.3 1_565 yes

_refine_diff_density_max         1.788
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.136

####################################################################### 
# 
# 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_xb6735_0m
_database_code_depnum_ccdc_archive 'CCDC 963676'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 Cu F3 N3 O3'
_chemical_formula_weight         340.75

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3596(14)
_cell_length_b                   7.6821(18)
_cell_length_c                   14.234(3)
_cell_angle_alpha                102.532(4)
_cell_angle_beta                 94.963(4)
_cell_angle_gamma                93.215(4)
_cell_volume                     674.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    536
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      19.34

_exptl_crystal_description       strip
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_F_000             342
_exptl_transmission_factor_min   0.6260
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.665
_shelx_estimated_absorpt_T_min   0.681
_shelx_estimated_absorpt_T_max   0.813
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3237
_diffrn_reflns_av_unetI/netI     0.0827
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.724
_diffrn_reflns_theta_max         24.505
_diffrn_reflns_theta_full        24.505
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2223
_reflns_number_gt                1494
_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-2018/1 (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)+(0.1060P)²+0.7953P] 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         2223
_refine_ls_number_parameters     185
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.2082
_refine_ls_wR_factor_gt          0.1684
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.103
_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 0.500000 0.500000 0.500000 0.0301(4) Uani 1 2 d S . P . .
Cu2 Cu 0.000000 0.500000 0.500000 0.0306(4) Uani 1 2 d S . P . .
O2 O 0.4125(8) 0.5825(8) 0.3840(4) 0.0420(15) Uani 1 1 d . . . . .
O1 O 0.0595(8) 0.5880(8) 0.3858(4) 0.0399(14) Uani 1 1 d . . . . .
C1 C 0.2250(13) 0.6003(10) 0.3496(5) 0.0331(19) Uani 1 1 d . . . . .
O3 O 0.2784(9) 0.7294(8) 0.5887(4) 0.0434(15) Uani 1 1 d . . . . .
H3A H 0.279536 0.819184 0.566282 0.052 Uiso 1 1 calc R U . . .
N1 N 0.2362(10) 0.3410(9) 0.4816(5) 0.0364(16) Uani 1 1 d . . . . .
C2 C 0.2135(13) 0.6476(10) 0.2509(5) 0.0345(19) Uani 1 1 d . . . . .
C7 C 0.3801(13) 0.6210(13) 0.1948(6) 0.048(2) Uani 1 1 d . . . . .
H7 H 0.500941 0.575064 0.218371 0.057 Uiso 1 1 calc R U . . .
N2 N 0.2360(11) 0.2024(10) 0.5079(6) 0.053(2) Uani 1 1 d . . . . .
C3 C 0.0348(15) 0.7142(14) 0.2157(7) 0.056(3) Uani 1 1 d . . . . .
H3 H -0.078711 0.731923 0.252876 0.067 Uiso 1 1 calc R U . . .
C6 C 0.3720(15) 0.6602(13) 0.1057(6) 0.052(3) Uani 1 1 d . . . . .
H6 H 0.486757 0.642586 0.069291 0.062 Uiso 1 1 calc R U . . .
C5 C 0.1887(14) 0.7274(12) 0.0693(6) 0.044(2) Uani 1 1 d . . . . .
F2 F 0.2644(13) 0.9338(11) -0.0256(5) 0.101(2) Uani 1 1 d . . . . .
F1 F -0.0099(12) 0.7597(12) -0.0709(5) 0.108(3) Uani 1 1 d . . . . .
F3 F 0.2897(14) 0.6642(12) -0.0894(5) 0.113(3) Uani 1 1 d . U . . .
C8 C 0.184(2) 0.7716(19) -0.0275(8) 0.081(4) Uani 1 1 d . . . . .
C4 C 0.0216(17) 0.7557(15) 0.1247(7) 0.064(3) Uani 1 1 d . . . . .
H4 H -0.099410 0.802238 0.101685 0.077 Uiso 1 1 calc R U . . .
N3 N 0.2344(16) 0.0700(14) 0.5325(9) 0.091(3) Uani 1 1 d . U . . .
C9 C 0.2903(18) 0.7801(15) 0.6908(7) 0.068(3) Uani 1 1 d . . . . .
H9A H 0.176361 0.855551 0.708770 0.081 Uiso 1 1 calc R U . . .
H9AB H 0.268334 0.673511 0.715968 0.081 Uiso 1 1 calc R U . . .
C10 C 0.484(2) 0.8725(19) 0.7350(9) 0.099(4) Uani 1 1 d . . . . .
H10A H 0.599487 0.805985 0.711152 0.148 Uiso 1 1 calc R U . . .
H10B H 0.489935 0.885758 0.803840 0.148 Uiso 1 1 calc R U . . .
H10C H 0.495654 0.988428 0.720069 0.148 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_666 ?
Cu1 O2 1.943(5) . ?
Cu1 N1 1.983(7) . ?
Cu1 N1 1.983(7) 2_666 ?
Cu1 O3 2.511(5) . ?
Cu2 O1 1.949(5) . ?
Cu2 O1 1.949(5) 2_566 ?
Cu2 N1 1.988(6) 2_566 ?
Cu2 N1 1.988(6) . ?
Cu2 O3 2.476(6) . ?
O2 C1 1.275(9) . ?
O1 C1 1.219(9) . ?
C1 C2 1.522(10) . ?
O3 C9 1.416(11) . ?
O3 H3A 0.8200 . ?
N1 N2 1.202(9) . ?
C2 C3 1.372(11) . ?
C2 C7 1.379(11) . ?
C7 C6 1.364(11) . ?
C7 H7 0.9300 . ?
N2 N3 1.146(11) . ?
C3 C4 1.396(12) . ?
C3 H3 0.9300 . ?
C6 C5 1.404(11) . ?
C6 H6 0.9300 . ?
C5 C4 1.377(13) . ?
C5 C8 1.487(12) . ?
F2 C8 1.314(15) . ?
F1 C8 1.320(14) . ?
F3 C8 1.326(12) . ?
C4 H4 0.9300 . ?
C9 C10 1.413(16) . ?
C9 H9A 0.9700 . ?
C9 H9AB 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 O2 180.0(3) 2_666 . ?
O2 Cu1 N1 89.4(3) 2_666 . ?
O2 Cu1 N1 90.6(3) . . ?
O2 Cu1 N1 90.6(3) 2_666 2_666 ?
O2 Cu1 N1 89.4(3) . 2_666 ?
N1 Cu1 N1 180.0 . 2_666 ?
O2 Cu1 O3 92.8(2) 2_666 . ?
O2 Cu1 O3 87.2(2) . . ?
N1 Cu1 O3 83.8(2) . . ?
N1 Cu1 O3 96.2(2) 2_666 . ?
O1 Cu2 O1 180.0 . 2_566 ?
O1 Cu2 N1 89.5(2) . 2_566 ?
O1 Cu2 N1 90.5(2) 2_566 2_566 ?
O1 Cu2 N1 90.5(2) . . ?
O1 Cu2 N1 89.5(2) 2_566 . ?
N1 Cu2 N1 180.0(3) 2_566 . ?
O1 Cu2 O3 85.9(2) . . ?
O1 Cu2 O3 94.1(2) 2_566 . ?
N1 Cu2 O3 95.4(2) 2_566 . ?
N1 Cu2 O3 84.6(2) . . ?
C1 O2 Cu1 128.1(5) . . ?
C1 O1 Cu2 130.1(5) . . ?
O1 C1 O2 128.8(7) . . ?
O1 C1 C2 117.4(7) . . ?
O2 C1 C2 113.8(7) . . ?
C9 O3 Cu2 119.3(6) . . ?
C9 O3 Cu1 123.2(6) . . ?
Cu2 O3 Cu1 79.22(16) . . ?
C9 O3 H3A 109.5 . . ?
Cu2 O3 H3A 111.3 . . ?
Cu1 O3 H3A 111.4 . . ?
N2 N1 Cu1 120.2(5) . . ?
N2 N1 Cu2 122.4(6) . . ?
Cu1 N1 Cu2 106.4(3) . . ?
C3 C2 C7 119.1(7) . . ?
C3 C2 C1 120.2(7) . . ?
C7 C2 C1 120.7(7) . . ?
C6 C7 C2 121.7(8) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
N3 N2 N1 179.5(11) . . ?
C2 C3 C4 120.7(8) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C7 C6 C5 119.4(8) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C4 C5 C6 119.6(8) . . ?
C4 C5 C8 121.8(8) . . ?
C6 C5 C8 118.6(9) . . ?
F2 C8 F1 105.9(9) . . ?
F2 C8 F3 105.0(11) . . ?
F1 C8 F3 104.9(10) . . ?
F2 C8 C5 114.0(10) . . ?
F1 C8 C5 112.5(11) . . ?
F3 C8 C5 113.8(9) . . ?
C5 C4 C3 119.6(8) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C10 C9 O3 114.1(10) . . ?
C10 C9 H9A 108.7 . . ?
O3 C9 H9A 108.7 . . ?
C10 C9 H9AB 108.7 . . ?
O3 C9 H9AB 108.7 . . ?
H9A C9 H9AB 107.6 . . ?
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 . . ?

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
Cu2 O1 C1 O2 -11.0(13) . . . . ?
Cu2 O1 C1 C2 170.6(5) . . . . ?
Cu1 O2 C1 O1 8.4(13) . . . . ?
Cu1 O2 C1 C2 -173.2(5) . . . . ?
O1 C1 C2 C3 14.9(12) . . . . ?
O2 C1 C2 C3 -163.7(8) . . . . ?
O1 C1 C2 C7 -163.7(8) . . . . ?
O2 C1 C2 C7 17.7(11) . . . . ?
C3 C2 C7 C6 0.4(14) . . . . ?
C1 C2 C7 C6 179.1(8) . . . . ?
C7 C2 C3 C4 -0.4(15) . . . . ?
C1 C2 C3 C4 -179.1(9) . . . . ?
C2 C7 C6 C5 -0.8(15) . . . . ?
C7 C6 C5 C4 1.2(15) . . . . ?
C7 C6 C5 C8 179.2(10) . . . . ?
C4 C5 C8 F2 91.7(15) . . . . ?
C6 C5 C8 F2 -86.3(12) . . . . ?
C4 C5 C8 F1 -28.8(16) . . . . ?
C6 C5 C8 F1 153.2(10) . . . . ?
C4 C5 C8 F3 -147.9(12) . . . . ?
C6 C5 C8 F3 34.1(17) . . . . ?
C6 C5 C4 C3 -1.2(16) . . . . ?
C8 C5 C4 C3 -179.1(11) . . . . ?
C2 C3 C4 C5 0.8(17) . . . . ?
Cu2 O3 C9 C10 163.6(9) . . . . ?
Cu1 O3 C9 C10 67.3(12) . . . . ?

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
O3 H3A N3 0.82 2.11 2.917(11) 166.9 1_565 yes

_refine_diff_density_max         0.556
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.139

####################################################################### 
# 
# 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_xb6945_0m
_database_code_depnum_ccdc_archive 'CCDC 1010471'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 Cu F3 N3 O3'
_chemical_formula_weight         354.78

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.409(2)
_cell_length_b                   7.792(3)
_cell_length_c                   14.448(5)
_cell_angle_alpha                100.724(6)
_cell_angle_beta                 94.544(6)
_cell_angle_gamma                91.601(7)
_cell_volume                     706.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    329
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      17.46

_exptl_crystal_description       bulk
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_F_000             358
_exptl_transmission_factor_min   0.6319
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.593
_shelx_estimated_absorpt_T_min   0.646
_shelx_estimated_absorpt_T_max   0.808
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3579
_diffrn_reflns_av_unetI/netI     0.1174
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.663
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2472
_reflns_number_gt                1599
_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-2018/1 (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)+(0.0496P)²+1.0930P] 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         2472
_refine_ls_number_parameters     194
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.1621
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.033
_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 0.500000 0.000000 0.500000 0.0280(4) Uani 1 2 d S . P . .
Cu2 Cu 0.000000 0.000000 0.500000 0.0281(4) Uani 1 2 d S . P . .
F1 F 0.2808(11) 0.1567(9) -0.0848(4) 0.101(2) Uani 1 1 d . U . . .
F2 F 0.2473(13) 0.4195(9) -0.0257(4) 0.113(3) Uani 1 1 d . . . . .
F3 F -0.0169(12) 0.2528(11) -0.0676(4) 0.110(3) Uani 1 1 d . . . . .
O1 O 0.4071(7) 0.0901(6) 0.3870(3) 0.0344(13) Uani 1 1 d . . . . .
O2 O 0.0565(8) 0.0894(7) 0.3863(3) 0.0370(13) Uani 1 1 d . . . . .
O3 O 0.2672(8) 0.2283(6) 0.5877(4) 0.0396(13) Uani 1 1 d . . . . .
H3 H 0.265118 0.313080 0.561497 0.048 Uiso 1 1 calc R U . . .
N1 N 0.2430(9) -0.1524(8) 0.4842(4) 0.0290(14) Uani 1 1 d . . . . .
N2 N 0.2421(9) -0.2959(10) 0.5043(5) 0.0439(18) Uani 1 1 d . . . . .
N3 N 0.2457(13) -0.4331(11) 0.5219(8) 0.089(3) Uani 1 1 d . . . . .
C1 C 0.2326(14) 0.2834(13) 0.6854(6) 0.061(3) Uani 1 1 d . . . . .
H1A H 0.235314 0.182470 0.715786 0.073 Uiso 1 1 calc R U . . .
H1AB H 0.094354 0.330387 0.689534 0.073 Uiso 1 1 calc R U . . .
C2 C 0.3917(16) 0.4189(12) 0.7376(6) 0.064(3) Uani 1 1 d . . . . .
H2A H 0.344932 0.465063 0.799214 0.076 Uiso 1 1 calc R U . . .
H2AB H 0.398482 0.514563 0.703375 0.076 Uiso 1 1 calc R U . . .
C3 C 0.6078(16) 0.3534(14) 0.7511(7) 0.076(3) Uani 1 1 d . . . . .
H3A H 0.702842 0.449316 0.779857 0.115 Uiso 1 1 calc R U . . .
H3B H 0.652554 0.300826 0.690806 0.115 Uiso 1 1 calc R U . . .
H3C H 0.606288 0.268066 0.791172 0.115 Uiso 1 1 calc R U . . .
C4 C 0.2271(11) 0.1059(9) 0.3504(5) 0.0286(17) Uani 1 1 d . . . . .
C5 C 0.2127(11) 0.1477(9) 0.2521(5) 0.0294(17) Uani 1 1 d . . . . .
C6 C 0.3839(12) 0.1290(10) 0.1993(5) 0.038(2) Uani 1 1 d . . . . .
H6 H 0.509723 0.094249 0.225184 0.046 Uiso 1 1 calc R U . . .
C7 C 0.3693(13) 0.1615(11) 0.1089(5) 0.046(2) Uani 1 1 d . . . . .
H7 H 0.483627 0.144093 0.072894 0.055 Uiso 1 1 calc R U . . .
C8 C 0.1867(14) 0.2197(10) 0.0711(5) 0.039(2) Uani 1 1 d . . . . .
C9 C 0.0148(13) 0.2417(11) 0.1233(6) 0.047(2) Uani 1 1 d . . . . .
H9 H -0.108917 0.280229 0.097579 0.057 Uiso 1 1 calc R U . . .
C10 C 0.0267(13) 0.2063(11) 0.2140(6) 0.044(2) Uani 1 1 d . . . . .
H10 H -0.088741 0.221403 0.249354 0.053 Uiso 1 1 calc R U . . .
C17 C 0.1767(18) 0.2610(14) -0.0258(7) 0.065(3) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.952(5) 2_656 ?
Cu1 O1 1.952(5) . ?
Cu1 N1 1.976(6) . ?
Cu1 N1 1.976(6) 2_656 ?
Cu1 O3 2.570(5) . ?
Cu2 O2 1.955(5) . ?
Cu2 O2 1.955(5) 2_556 ?
Cu2 N1 1.987(6) 2_556 ?
Cu2 N1 1.987(6) . ?
Cu2 O3 2.520(5) . ?
F1 C17 1.302(11) . ?
F2 C17 1.303(11) . ?
F3 C17 1.331(11) . ?
O1 C4 1.249(8) . ?
O2 C4 1.260(8) . ?
O3 C1 1.433(9) . ?
O3 H3 0.8200 . ?
N1 N2 1.207(8) . ?
N2 N3 1.144(9) . ?
C1 C2 1.499(12) . ?
C1 H1A 0.9700 . ?
C1 H1AB 0.9700 . ?
C2 C3 1.500(13) . ?
C2 H2A 0.9700 . ?
C2 H2AB 0.9700 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.512(9) . ?
C5 C6 1.381(10) . ?
C5 C10 1.398(10) . ?
C6 C7 1.374(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(11) . ?
C7 H7 0.9300 . ?
C8 C9 1.381(11) . ?
C8 C17 1.491(11) . ?
C9 C10 1.385(10) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?

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 180.0 2_656 . ?
O1 Cu1 N1 89.7(2) 2_656 . ?
O1 Cu1 N1 90.3(2) . . ?
O1 Cu1 N1 90.3(2) 2_656 2_656 ?
O1 Cu1 N1 89.7(2) . 2_656 ?
N1 Cu1 N1 180.00(19) . 2_656 ?
O1 Cu1 O3 94.22(19) 2_656 . ?
O1 Cu1 O3 85.78(19) . . ?
N1 Cu1 O3 83.4(2) . . ?
N1 Cu1 O3 96.6(2) 2_656 . ?
O2 Cu2 O2 180.0(3) . 2_556 ?
O2 Cu2 N1 89.6(2) . 2_556 ?
O2 Cu2 N1 90.4(2) 2_556 2_556 ?
O2 Cu2 N1 90.4(2) . . ?
O2 Cu2 N1 89.6(2) 2_556 . ?
N1 Cu2 N1 180.0 2_556 . ?
O2 Cu2 O3 86.59(19) . . ?
O2 Cu2 O3 93.41(19) 2_556 . ?
N1 Cu2 O3 95.4(2) 2_556 . ?
N1 Cu2 O3 84.6(2) . . ?
C4 O1 Cu1 130.8(5) . . ?
C4 O2 Cu2 129.9(5) . . ?
C1 O3 Cu2 113.2(5) . . ?
C1 O3 Cu1 133.4(5) . . ?
Cu2 O3 Cu1 78.03(14) . . ?
C1 O3 H3 109.5 . . ?
Cu2 O3 H3 108.7 . . ?
Cu1 O3 H3 108.5 . . ?
N2 N1 Cu1 122.3(5) . . ?
N2 N1 Cu2 122.3(5) . . ?
Cu1 N1 Cu2 107.9(3) . . ?
N3 N2 N1 178.1(9) . . ?
O3 C1 C2 113.3(7) . . ?
O3 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
O3 C1 H1AB 108.9 . . ?
C2 C1 H1AB 108.9 . . ?
H1A C1 H1AB 107.7 . . ?
C1 C2 C3 114.4(8) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2AB 108.7 . . ?
C3 C2 H2AB 108.7 . . ?
H2A C2 H2AB 107.6 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 O2 127.0(7) . . ?
O1 C4 C5 116.4(6) . . ?
O2 C4 C5 116.6(6) . . ?
C6 C5 C10 119.4(7) . . ?
C6 C5 C4 120.2(6) . . ?
C10 C5 C4 120.4(7) . . ?
C7 C6 C5 120.3(7) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.5(8) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 120.1(7) . . ?
C7 C8 C17 119.6(8) . . ?
C9 C8 C17 120.3(8) . . ?
C8 C9 C10 119.9(7) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C5 119.8(8) . . ?
C9 C10 H10 120.1 . . ?
C5 C10 H10 120.1 . . ?
F1 C17 F2 106.8(9) . . ?
F1 C17 F3 104.8(9) . . ?
F2 C17 F3 104.6(9) . . ?
F1 C17 C8 114.0(8) . . ?
F2 C17 C8 112.3(9) . . ?
F3 C17 C8 113.6(9) . . ?

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
Cu2 O3 C1 C2 179.9(6) . . . . ?
Cu1 O3 C1 C2 84.4(9) . . . . ?
O3 C1 C2 C3 -68.6(11) . . . . ?
Cu1 O1 C4 O2 11.1(12) . . . . ?
Cu1 O1 C4 C5 -168.3(5) . . . . ?
Cu2 O2 C4 O1 -10.5(12) . . . . ?
Cu2 O2 C4 C5 168.8(4) . . . . ?
O1 C4 C5 C6 14.1(10) . . . . ?
O2 C4 C5 C6 -165.3(7) . . . . ?
O1 C4 C5 C10 -165.5(7) . . . . ?
O2 C4 C5 C10 15.1(10) . . . . ?
C10 C5 C6 C7 -2.4(12) . . . . ?
C4 C5 C6 C7 177.9(7) . . . . ?
C5 C6 C7 C8 2.6(13) . . . . ?
C6 C7 C8 C9 -1.6(13) . . . . ?
C6 C7 C8 C17 177.6(8) . . . . ?
C7 C8 C9 C10 0.4(13) . . . . ?
C17 C8 C9 C10 -178.7(8) . . . . ?
C8 C9 C10 C5 -0.3(13) . . . . ?
C6 C5 C10 C9 1.2(12) . . . . ?
C4 C5 C10 C9 -179.1(7) . . . . ?
C7 C8 C17 F1 36.7(13) . . . . ?
C9 C8 C17 F1 -144.2(9) . . . . ?
C7 C8 C17 F2 -84.9(11) . . . . ?
C9 C8 C17 F2 94.2(12) . . . . ?
C7 C8 C17 F3 156.6(9) . . . . ?
C9 C8 C17 F3 -24.2(13) . . . . ?

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
O3 H3 N3 0.82 2.16 2.969(9) 167.7 1_565 yes

_refine_diff_density_max         0.572
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.114

