# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_cucyclamcf6_true
_database_code_depnum_ccdc_archive 'CCDC 1851180'
_audit_update_record             
;
2018-06-22 deposited with the CCDC.
2018-10-04 downloaded from the CCDC.
;
_audit_creation_date             2017-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H26 Cu F6 N4, 2(Cl O4)'
_chemical_formula_sum            'C14 H26 Cl2 Cu F6 N4 O8'
_chemical_formula_weight         626.83
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.176(2)
_cell_length_b                   8.598(2)
_cell_length_c                   9.537(3)
_cell_angle_alpha                71.597(7)
_cell_angle_beta                 70.183(7)
_cell_angle_gamma                72.123(7)
_cell_volume                     583.3(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6114
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.82
_cell_measurement_theta_min      2.336
_shelx_estimated_absorpt_T_max   0.756
_shelx_estimated_absorpt_T_min   0.718
_exptl_absorpt_coefficient_mu    1.262
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS. Sheldrick, G. M. (2008). Bruker AXS Inc., Madison, WI, USA.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             319
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.235
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2362
_diffrn_reflns_av_unetI/netI     0.0943
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12193
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.022
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         2.336
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius Kappa CCD with Bruker Apex II CCD'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed fine-focus tube'
_diffrn_source_type              'Nonius Kappa CCD with Bruker Apex II CCD'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1753
_reflns_number_total             2055
_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       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_collection       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.956
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.094
_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)+(0.0740P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1339
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.500000 0.500000 0.500000 0.0201(2) Uani 1 2 d S T P . .
F1 F 0.8469(4) 0.8087(4) 0.0087(3) 0.0786(9) Uani 1 1 d . . . . .
F2 F 0.6415(4) 1.0039(4) 0.0862(4) 0.1002(11) Uani 1 1 d . . . . .
F3 F 0.8808(5) 0.9336(4) 0.1513(3) 0.0945(11) Uani 1 1 d . . . . .
N1 N 0.5508(4) 0.6723(3) 0.2834(3) 0.0280(6) Uani 1 1 d . . . . .
N2 N 0.2901(4) 0.6765(3) 0.5685(3) 0.0282(6) Uani 1 1 d . . . . .
H2 H 0.184896 0.641971 0.571776 0.034 Uiso 1 1 calc R . . . .
C1 C 0.7647(6) 0.8731(5) 0.1288(4) 0.0488(10) Uani 1 1 d . . . . .
C2 C 0.6947(5) 0.7487(4) 0.2731(4) 0.0348(8) Uani 1 1 d . . . . .
H2A H 0.795338 0.657410 0.292298 0.042 Uiso 1 1 calc R . . . .
H2B H 0.653496 0.804317 0.356927 0.042 Uiso 1 1 calc R . . . .
C3 C 0.2993(5) 0.8350(4) 0.4466(4) 0.0425(9) Uani 1 1 d . . . . .
H3A H 0.374834 0.893951 0.459993 0.051 Uiso 1 1 calc R . . . .
H3B H 0.181025 0.907537 0.454082 0.051 Uiso 1 1 calc R . . . .
C4 C 0.3737(5) 0.7944(5) 0.2925(4) 0.0432(10) Uani 1 1 d . . . . .
H4A H 0.387583 0.896773 0.213388 0.052 Uiso 1 1 calc R . . . .
H4B H 0.291498 0.746304 0.275038 0.052 Uiso 1 1 calc R . . . .
C5 C 0.5946(5) 0.5875(5) 0.1565(4) 0.0408(9) Uani 1 1 d . . . . .
H5A H 0.610544 0.670822 0.059662 0.049 Uiso 1 1 calc R . . . .
H5B H 0.494204 0.542421 0.168403 0.049 Uiso 1 1 calc R . . . .
C6 C 0.7600(5) 0.4469(5) 0.1499(4) 0.0455(10) Uani 1 1 d . . . . .
H6A H 0.791745 0.414236 0.053857 0.055 Uiso 1 1 calc R . . . .
H6B H 0.857221 0.489418 0.149334 0.055 Uiso 1 1 calc R . . . .
C7 C 0.2571(5) 0.7078(5) 0.7202(4) 0.0403(9) Uani 1 1 d . . . . .
H7A H 0.148425 0.793789 0.738940 0.048 Uiso 1 1 calc R . . . .
H7B H 0.354427 0.750806 0.718961 0.048 Uiso 1 1 calc R . . . .
Cl1 Cl 0.20383(11) 0.33889(11) 0.34954(10) 0.0373(3) Uani 1 1 d . . . . .
O1 O 0.3364(5) 0.2319(5) 0.2626(5) 0.1003(14) Uani 1 1 d . . . . .
O2 O 0.0863(4) 0.2484(4) 0.4721(4) 0.0771(10) Uani 1 1 d . . . . .
O3 O 0.2842(4) 0.4207(4) 0.4096(3) 0.0585(9) Uani 1 1 d . . . . .
O4 O 0.1046(6) 0.4663(6) 0.2543(5) 0.1052(15) 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 N1 2.121(2) . ?
Cu1 N1 2.121(2) 2_666 ?
Cu1 N2 1.985(3) 2_666 ?
Cu1 N2 1.985(3) . ?
F1 C1 1.311(5) . ?
F2 C1 1.318(5) . ?
F3 C1 1.316(5) . ?
N1 C2 1.477(4) . ?
N1 C4 1.499(4) . ?
N1 C5 1.493(5) . ?
N2 C3 1.489(4) . ?
N2 C7 1.475(4) . ?
C1 C2 1.510(5) . ?
C3 C4 1.496(5) . ?
C5 C6 1.510(6) . ?
C6 C7 1.510(5) 2_666 ?
Cl1 O1 1.403(4) . ?
Cl1 O2 1.420(3) . ?
Cl1 O3 1.431(3) . ?
Cl1 O4 1.417(3) . ?

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 180.0 . 2_666 ?
N2 Cu1 N1 92.84(11) 2_666 . ?
N2 Cu1 N1 87.16(11) 2_666 2_666 ?
N2 Cu1 N1 92.84(11) . 2_666 ?
N2 Cu1 N1 87.16(11) . . ?
N2 Cu1 N2 180.0 2_666 . ?
C2 N1 Cu1 108.07(18) . . ?
C2 N1 C4 113.1(3) . . ?
C2 N1 C5 112.8(3) . . ?
C4 N1 Cu1 101.46(19) . . ?
C5 N1 Cu1 110.9(2) . . ?
C5 N1 C4 110.0(3) . . ?
C3 N2 Cu1 108.0(2) . . ?
C7 N2 Cu1 118.4(2) . . ?
C7 N2 C3 110.6(3) . . ?
F1 C1 F2 105.8(4) . . ?
F1 C1 F3 106.7(3) . . ?
F1 C1 C2 114.2(3) . . ?
F2 C1 C2 114.3(3) . . ?
F3 C1 F2 106.3(4) . . ?
F3 C1 C2 109.1(4) . . ?
N1 C2 C1 120.3(3) . . ?
N2 C3 C4 109.5(3) . . ?
C3 C4 N1 110.4(3) . . ?
N1 C5 C6 114.1(3) . . ?
C7 C6 C5 115.0(3) 2_666 . ?
N2 C7 C6 113.5(3) . 2_666 ?
O1 Cl1 O2 111.2(2) . . ?
O1 Cl1 O3 110.0(2) . . ?
O1 Cl1 O4 109.7(3) . . ?
O2 Cl1 O3 109.57(19) . . ?
O4 Cl1 O2 109.2(2) . . ?
O4 Cl1 O3 107.2(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_vrf_RINTA01_cucyclamcf6_true    
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: Data collection was taken at room temperature due to issues with the 
cold stream which may have resulted in error in the intensities.
;
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1851181'
_audit_update_record             
;
2018-06-22 deposited with the CCDC.
2018-10-04 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         'C26 H34 N4 F6, Cu 2+, 2 Cl O4 1-'
_chemical_formula_sum            'C26 H34 Cl2 Cu F6 N4 O8'
_chemical_formula_weight         779.01

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'
Cl Cl 0.1484 0.1585 '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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.2343(10)
_cell_length_b                   8.8063(12)
_cell_length_c                   20.987(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.076(3)
_cell_angle_gamma                90
_cell_volume                     1502.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    106(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      29.6

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_F_000             798
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.999
_shelx_estimated_absorpt_T_min   0.691
_shelx_estimated_absorpt_T_max   0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
SADABS. G. M. Sheldrick. Apex II release 2010, Bruker AXS, Inc.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      106(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD with Bruker Apex II detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23409
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.965
_diffrn_reflns_theta_max         29.605
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4214
_reflns_number_gt                3754
_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       'Apex II release 2010, Bruker AXS, Inc.'
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2014/7, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'






_refine_special_details          
;
The Cu complex resides on a crystallographic inversion center.  The Cu ion is 
located at 1/2, 1/2, 1/2.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+0.9990P] 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_number_reflns         4214
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0718
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
Cu1 Cu 0.5000 0.5000 0.5000 0.00655(6) Uani 1 2 d S . P . .
F1 F 0.78760(12) 0.93388(11) 0.76085(4) 0.0232(2) Uani 1 1 d . . . . .
F2 F 0.76677(11) 0.86112(10) 0.66221(4) 0.01701(18) Uani 1 1 d . . . . .
F3 F 0.55748(10) 0.84688(11) 0.71215(4) 0.02021(19) Uani 1 1 d . . . . .
N1 N 0.54470(13) 0.47942(13) 0.60182(5) 0.0090(2) Uani 1 1 d . . . . .
N2 N 0.37445(13) 0.68657(13) 0.51357(5) 0.0087(2) Uani 1 1 d . . . . .
C1 C 0.41373(16) 0.57766(16) 0.62163(6) 0.0116(2) Uani 1 1 d . . . . .
H1A H 0.4400 0.6003 0.6683 0.014 Uiso 1 1 calc R U . . .
H1B H 0.3069 0.5239 0.6137 0.014 Uiso 1 1 calc R U . . .
C2 C 0.40209(16) 0.72404(16) 0.58347(6) 0.0118(2) Uani 1 1 d . . . . .
H2A H 0.3100 0.7864 0.5940 0.014 Uiso 1 1 calc R U . . .
H2B H 0.5051 0.7829 0.5946 0.014 Uiso 1 1 calc R U . . .
C3 C 0.40580(17) 0.82329(15) 0.47568(7) 0.0129(3) Uani 1 1 d . . . . .
H3A H 0.5222 0.8540 0.4878 0.016 Uiso 1 1 calc R U . . .
H3B H 0.3363 0.9079 0.4869 0.016 Uiso 1 1 calc R U . . .
C4 C 0.37029(17) 0.79699(16) 0.40348(7) 0.0139(3) Uani 1 1 d . . . . .
H4A H 0.3813 0.8948 0.3813 0.017 Uiso 1 1 calc R U . . .
H4B H 0.2548 0.7631 0.3918 0.017 Uiso 1 1 calc R U . . .
C5 C 0.48194(16) 0.68030(16) 0.37849(7) 0.0121(2) Uani 1 1 d . . . . .
H5A H 0.4647 0.6854 0.3308 0.015 Uiso 1 1 calc R U . . .
H5B H 0.5978 0.7083 0.3942 0.015 Uiso 1 1 calc R U . . .
C6 C 0.71382(15) 0.53806(16) 0.62906(6) 0.0101(2) Uani 1 1 d . . . . .
H6A H 0.7230 0.6434 0.6136 0.012 Uiso 1 1 calc R U . . .
H6B H 0.7958 0.4762 0.6108 0.012 Uiso 1 1 calc R U . . .
C7 C 0.76124(16) 0.53822(17) 0.70262(6) 0.0120(2) Uani 1 1 d . . . . .
C8 C 0.77089(16) 0.66751(17) 0.74284(7) 0.0135(3) Uani 1 1 d . . . . .
C9 C 0.82628(17) 0.65395(19) 0.80948(7) 0.0180(3) Uani 1 1 d . . . . .
H9 H 0.8340 0.7422 0.8358 0.022 Uiso 1 1 calc R U . . .
C10 C 0.86979(19) 0.5144(2) 0.83740(7) 0.0206(3) Uani 1 1 d . . . . .
H10 H 0.9048 0.5065 0.8826 0.025 Uiso 1 1 calc R U . . .
C11 C 0.86171(17) 0.38671(19) 0.79877(7) 0.0181(3) Uani 1 1 d . . . . .
H11 H 0.8907 0.2902 0.8174 0.022 Uiso 1 1 calc R U . . .
C12 C 0.81091(16) 0.39986(17) 0.73251(7) 0.0147(3) Uani 1 1 d . . . . .
H12 H 0.8099 0.3115 0.7065 0.018 Uiso 1 1 calc R U . . .
C13 C 0.72261(17) 0.82537(17) 0.71948(7) 0.0154(3) Uani 1 1 d . . . . .
Cl1 Cl 0.91147(4) 0.72767(4) 0.50270(2) 0.01196(8) Uani 1 1 d . . . . .
O1 O 0.78184(12) 0.61438(12) 0.49411(5) 0.0163(2) Uani 1 1 d . . . . .
O2 O 1.00769(13) 0.71253(15) 0.45129(5) 0.0227(2) Uani 1 1 d . . . . .
O3 O 1.01554(14) 0.70219(16) 0.56349(5) 0.0268(3) Uani 1 1 d . . . . .
O4 O 0.83839(16) 0.87514(14) 0.50078(9) 0.0398(4) Uani 1 1 d . . . . .
H2N H 0.275(2) 0.666(2) 0.5033(9) 0.013(4) Uiso 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 N2 1.9855(11) 3_666 ?
Cu1 N2 1.9855(11) . ?
Cu1 N1 2.1181(12) . ?
Cu1 N1 2.1182(12) 3_666 ?
F1 C13 1.3442(16) . ?
F2 C13 1.3468(17) . ?
F3 C13 1.3574(16) . ?
N1 C1 1.4919(16) . ?
N1 C5 1.4920(17) 3_666 ?
N1 C6 1.5105(16) . ?
N2 C2 1.4857(17) . ?
N2 C3 1.4878(17) . ?
N2 H2N 0.836(19) . ?
C1 C2 1.513(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.515(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5259(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.4920(17) 3_666 ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5316(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.402(2) . ?
C7 C8 1.412(2) . ?
C8 C9 1.406(2) . ?
C8 C13 1.507(2) . ?
C9 C10 1.384(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
Cl1 O4 1.4292(13) . ?
Cl1 O3 1.4378(12) . ?
Cl1 O2 1.4420(11) . ?
Cl1 O1 1.4514(10) . ?

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
N2 Cu1 N2 180.0 3_666 . ?
N2 Cu1 N1 93.58(4) 3_666 . ?
N2 Cu1 N1 86.42(4) . . ?
N2 Cu1 N1 86.42(4) 3_666 3_666 ?
N2 Cu1 N1 93.58(4) . 3_666 ?
N1 Cu1 N1 180.0 . 3_666 ?
C1 N1 C5 108.98(10) . 3_666 ?
C1 N1 C6 111.10(10) . . ?
C5 N1 C6 112.61(10) 3_666 . ?
C1 N1 Cu1 102.32(8) . . ?
C5 N1 Cu1 110.51(8) 3_666 . ?
C6 N1 Cu1 110.84(8) . . ?
C2 N2 C3 109.61(11) . . ?
C2 N2 Cu1 108.86(8) . . ?
C3 N2 Cu1 117.05(8) . . ?
C2 N2 H2N 107.1(13) . . ?
C3 N2 H2N 106.6(13) . . ?
Cu1 N2 H2N 107.1(13) . . ?
N1 C1 C2 109.56(10) . . ?
N1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
N2 C2 C1 108.69(11) . . ?
N2 C2 H2A 110.0 . . ?
C1 C2 H2A 110.0 . . ?
N2 C2 H2B 110.0 . . ?
C1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.3 . . ?
N2 C3 C4 112.86(11) . . ?
N2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
N2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 C5 114.52(11) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
N1 C5 C4 114.64(11) 3_666 . ?
N1 C5 H5A 108.6 3_666 . ?
C4 C5 H5A 108.6 . . ?
N1 C5 H5B 108.6 3_666 . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
N1 C6 C7 117.07(10) . . ?
N1 C6 H6A 108.0 . . ?
C7 C6 H6A 108.0 . . ?
N1 C6 H6B 108.0 . . ?
C7 C6 H6B 108.0 . . ?
H6A C6 H6B 107.3 . . ?
C12 C7 C8 116.65(12) . . ?
C12 C7 C6 117.41(13) . . ?
C8 C7 C6 125.77(13) . . ?
C9 C8 C7 120.33(14) . . ?
C9 C8 C13 115.44(13) . . ?
C7 C8 C13 124.23(12) . . ?
C10 C9 C8 121.22(14) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 119.26(14) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 119.83(15) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C7 122.67(14) . . ?
C11 C12 H12 118.7 . . ?
C7 C12 H12 118.7 . . ?
F1 C13 F2 105.92(12) . . ?
F1 C13 F3 105.28(11) . . ?
F2 C13 F3 105.84(11) . . ?
F1 C13 C8 112.84(12) . . ?
F2 C13 C8 114.31(12) . . ?
F3 C13 C8 111.95(12) . . ?
O4 Cl1 O3 110.87(9) . . ?
O4 Cl1 O2 109.97(8) . . ?
O3 Cl1 O2 109.18(7) . . ?
O4 Cl1 O1 108.84(7) . . ?
O3 Cl1 O1 109.07(7) . . ?
O2 Cl1 O1 108.88(7) . . ?

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 N1 C1 C2 -160.78(11) 3_666 . . . ?
C6 N1 C1 C2 74.57(13) . . . . ?
Cu1 N1 C1 C2 -43.76(11) . . . . ?
C3 N2 C2 C1 -165.34(10) . . . . ?
Cu1 N2 C2 C1 -36.15(12) . . . . ?
N1 C1 C2 N2 55.43(13) . . . . ?
C2 N2 C3 C4 -176.54(11) . . . . ?
Cu1 N2 C3 C4 58.89(13) . . . . ?
N2 C3 C4 C5 -64.74(15) . . . . ?
C3 C4 C5 N1 69.31(15) . . . 3_666 ?
C1 N1 C6 C7 63.96(15) . . . . ?
C5 N1 C6 C7 -58.62(15) 3_666 . . . ?
Cu1 N1 C6 C7 177.01(9) . . . . ?
N1 C6 C7 C12 79.00(15) . . . . ?
N1 C6 C7 C8 -105.86(15) . . . . ?
C12 C7 C8 C9 -0.71(19) . . . . ?
C6 C7 C8 C9 -175.89(12) . . . . ?
C12 C7 C8 C13 -179.84(13) . . . . ?
C6 C7 C8 C13 5.0(2) . . . . ?
C7 C8 C9 C10 -1.1(2) . . . . ?
C13 C8 C9 C10 178.09(13) . . . . ?
C8 C9 C10 C11 1.3(2) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 C7 -2.2(2) . . . . ?
C8 C7 C12 C11 2.4(2) . . . . ?
C6 C7 C12 C11 177.97(12) . . . . ?
C9 C8 C13 F1 19.92(17) . . . . ?
C7 C8 C13 F1 -160.92(13) . . . . ?
C9 C8 C13 F2 141.03(12) . . . . ?
C7 C8 C13 F2 -39.81(18) . . . . ?
C9 C8 C13 F3 -98.64(14) . . . . ?
C7 C8 C13 F3 80.52(16) . . . . ?

_refine_diff_density_max         0.524
_refine_diff_density_min         -0.397
_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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1851182'
_audit_update_record             
;
2018-06-22 deposited with the CCDC.
2018-10-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT213_shelx               
;
PROBLEM: Atom F2              has ADP max/min Ratio .....        4.2 prolat
RESPONSE: The CF3 group and the perchlorate groups displayed some elongated 
displacement parameters common in such groups.  C12 did as well although I 
don't have an explanation for that observation.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H29 N4 F3, Cu 2+, 2 Cl O4 1-'
_chemical_formula_sum            'C18 H29 Cl2 Cu F3 N4 O8'
_chemical_formula_weight         620.89

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'
Cl Cl 0.1484 0.1585 '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                   8.0393(18)
_cell_length_b                   8.317(2)
_cell_length_c                   17.362(3)
_cell_angle_alpha                87.878(7)
_cell_angle_beta                 84.964(8)
_cell_angle_gamma                88.185(6)
_cell_volume                     1155.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4535
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      22.3

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale violet'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_F_000             638
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.256
_shelx_estimated_absorpt_T_min   0.770
_shelx_estimated_absorpt_T_max   0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
SADABS. G. M. Sheldrick. Apex II release 2010, Bruker AXS, Inc.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed fine focus tube'
_diffrn_measurement_device_type  ω-scans
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26201
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.357
_diffrn_reflns_theta_max         25.037
_diffrn_reflns_theta_full        25.037
_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             4074
_reflns_number_gt                3244
_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       'Apex II release 2010, Bruker AXS, Inc.'
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2014/7, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'





_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)+(0.0206P)²+0.9600P] 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         4074
_refine_ls_number_parameters     325
_refine_ls_number_restraints     342
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0728
_refine_ls_wR_factor_gt          0.0679
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.009
_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
C1 C -0.0433(3) 0.6774(3) 0.31070(16) 0.0099(6) Uani 1 1 d . U . . .
H1A H -0.0866 0.6443 0.3639 0.012 Uiso 1 1 calc R U . . .
H1B H -0.0729 0.5936 0.2756 0.012 Uiso 1 1 calc R U . . .
C2 C -0.1298(3) 0.8359(3) 0.28825(16) 0.0123(7) Uani 1 1 d . U . . .
H2A H -0.2505 0.8293 0.3049 0.015 Uiso 1 1 calc R U . . .
H2B H -0.0849 0.9232 0.3170 0.015 Uiso 1 1 calc R U . . .
C3 C -0.1099(3) 0.8807(3) 0.20259(15) 0.0110(6) Uani 1 1 d . U . . .
H3A H -0.1589 0.7958 0.1739 0.013 Uiso 1 1 calc R U . . .
H3B H -0.1738 0.9823 0.1934 0.013 Uiso 1 1 calc R U . . .
C4 C 0.0723(3) 0.9288(3) 0.08546(15) 0.0090(6) Uani 1 1 d . U . . .
H4A H 0.0266 1.0377 0.0731 0.011 Uiso 1 1 calc R U . . .
H4B H 0.0036 0.8489 0.0629 0.011 Uiso 1 1 calc R U . . .
C5 C 0.2516(3) 0.9126(3) 0.05169(16) 0.0096(6) Uani 1 1 d . U . . .
H5A H 0.2571 0.9194 -0.0055 0.012 Uiso 1 1 calc R U . . .
H5B H 0.3181 1.0001 0.0694 0.012 Uiso 1 1 calc R U . . .
C6 C 0.5018(3) 0.7361(3) 0.05764(16) 0.0105(6) Uani 1 1 d . U . . .
H6A H 0.5591 0.8226 0.0816 0.013 Uiso 1 1 calc R U . . .
H6B H 0.5244 0.7491 0.0008 0.013 Uiso 1 1 calc R U . . .
C7 C 0.5719(4) 0.5742(3) 0.08413(15) 0.0121(7) Uani 1 1 d . U . . .
H7A H 0.6893 0.5628 0.0620 0.015 Uiso 1 1 calc R U . . .
H7B H 0.5082 0.4886 0.0630 0.015 Uiso 1 1 calc R U . . .
C8 C 0.5672(3) 0.5477(4) 0.17136(15) 0.0102(6) Uani 1 1 d . U . . .
H8A H 0.6319 0.4480 0.1834 0.012 Uiso 1 1 calc R U . . .
H8B H 0.6204 0.6387 0.1938 0.012 Uiso 1 1 calc R U . . .
C9 C 0.3926(3) 0.5043(3) 0.29176(15) 0.0106(6) Uani 1 1 d . U . . .
H9A H 0.4632 0.5831 0.3139 0.013 Uiso 1 1 calc R U . . .
H9B H 0.4381 0.3948 0.3030 0.013 Uiso 1 1 calc R U . . .
C10 C 0.2143(3) 0.5212(3) 0.32703(16) 0.0098(6) Uani 1 1 d . U . . .
H10A H 0.1460 0.4378 0.3070 0.012 Uiso 1 1 calc R U . . .
H10B H 0.2114 0.5053 0.3839 0.012 Uiso 1 1 calc R U . . .
C11 C 0.2046(3) 0.8076(3) 0.35936(15) 0.0093(6) Uani 1 1 d . U . . .
H11A H 0.1600 0.9144 0.3427 0.011 Uiso 1 1 calc R U . . .
H11B H 0.3278 0.8099 0.3499 0.011 Uiso 1 1 calc R U . . .
C12 C 0.1613(4) 0.7869(3) 0.44680(15) 0.0101(6) Uani 1 1 d . U . . .
C13 C 0.2840(4) 0.7631(3) 0.50001(16) 0.0134(7) Uani 1 1 d . U . . .
C14 C 0.2393(4) 0.7562(3) 0.57962(16) 0.0165(7) Uani 1 1 d . U . . .
H14 H 0.3235 0.7402 0.6145 0.020 Uiso 1 1 calc R U . . .
C15 C 0.0743(4) 0.7722(3) 0.60821(17) 0.0157(7) Uani 1 1 d . U . . .
H15 H 0.0446 0.7654 0.6624 0.019 Uiso 1 1 calc R U . . .
C16 C -0.0477(4) 0.7982(3) 0.55737(16) 0.0150(7) Uani 1 1 d . U . . .
H16 H -0.1615 0.8106 0.5766 0.018 Uiso 1 1 calc R U . . .
C17 C -0.0040(4) 0.8062(3) 0.47823(16) 0.0120(7) Uani 1 1 d . U . . .
H17 H -0.0894 0.8255 0.4442 0.014 Uiso 1 1 calc R U . . .
C18 C 0.4677(4) 0.7552(4) 0.47571(17) 0.0231(8) Uani 1 1 d . U . . .
N1 N 0.1435(3) 0.6840(3) 0.30756(12) 0.0070(5) Uani 1 1 d . U . . .
N2 N 0.3925(3) 0.5340(3) 0.20720(12) 0.0078(5) Uani 1 1 d . U . . .
H2N H 0.3438 0.4382 0.1854 0.009 Uiso 1 1 calc R U . . .
N3 N 0.3187(3) 0.7532(3) 0.07852(12) 0.0082(5) Uani 1 1 d . U . . .
H3N H 0.2646 0.6698 0.0499 0.010 Uiso 1 1 calc R U . . .
N4 N 0.0666(3) 0.9014(3) 0.17108(12) 0.0070(5) Uani 1 1 d . U . . .
H4N H 0.1061 1.0014 0.1931 0.008 Uiso 1 1 calc R U . . .
O1 O 0.4583(2) 0.9051(2) 0.22129(10) 0.0126(5) Uani 1 1 d . U . . .
O2 O 0.2933(2) 1.1400(2) 0.24869(12) 0.0171(5) Uani 1 1 d . U . . .
O3 O 0.5706(3) 1.1178(2) 0.28392(12) 0.0209(5) Uani 1 1 d . U . . .
O4 O 0.5197(3) 1.1486(3) 0.15266(12) 0.0231(5) Uani 1 1 d . U . . .
O6 O 0.1951(2) 0.3390(3) 0.09037(11) 0.0202(5) Uani 1 1 d . U . . .
O5 O 0.0054(2) 0.5460(2) 0.13277(11) 0.0167(5) Uani 1 1 d . U . . .
O7 O -0.0841(2) 0.3380(2) 0.05805(11) 0.0177(5) Uani 1 1 d . U . . .
O8 O -0.0234(3) 0.2838(2) 0.18674(11) 0.0199(5) Uani 1 1 d . U . . .
F1 F 0.5136(2) 0.6230(2) 0.43456(10) 0.0337(5) Uani 1 1 d . U . . .
F2 F 0.5621(2) 0.7469(3) 0.53598(10) 0.0358(5) Uani 1 1 d . U . . .
F3 F 0.5205(2) 0.8817(3) 0.43100(10) 0.0343(5) Uani 1 1 d . U . . .
Cu1 Cu 0.23500(4) 0.72345(4) 0.19152(2) 0.00696(11) Uani 1 1 d . U . . .
Cl1 Cl 0.46116(9) 1.07959(8) 0.22661(4) 0.01062(17) Uani 1 1 d . U . . .
Cl2 Cl 0.02275(8) 0.37543(8) 0.11673(4) 0.00949(17) Uani 1 1 d . 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
C1 N1 1.501(3) . ?
C1 C2 1.525(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.516(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N4 1.488(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N4 1.493(3) . ?
C4 C5 1.511(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N3 1.490(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N3 1.488(3) . ?
C6 C7 1.515(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.520(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.492(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N2 1.480(3) . ?
C9 C10 1.512(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N1 1.491(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N1 1.511(3) . ?
C11 C12 1.532(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.399(4) . ?
C12 C13 1.414(4) . ?
C13 C14 1.397(4) . ?
C13 C18 1.500(4) . ?
C14 C15 1.379(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 F3 1.342(4) . ?
C18 F2 1.344(3) . ?
C18 F1 1.356(4) . ?
N1 Cu1 2.101(2) . ?
N2 Cu1 2.015(2) . ?
N2 H2N 1.0000 . ?
N3 Cu1 2.026(2) . ?
N3 H3N 1.0000 . ?
N4 Cu1 2.017(2) . ?
N4 H4N 1.0000 . ?
O1 Cl1 1.4589(19) . ?
O2 Cl1 1.450(2) . ?
O3 Cl1 1.435(2) . ?
O4 Cl1 1.434(2) . ?
O6 Cl2 1.447(2) . ?
O5 Cl2 1.456(2) . ?
O7 Cl2 1.438(2) . ?
O8 Cl2 1.438(2) . ?

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 C1 C2 114.3(2) . . ?
N1 C1 H1A 108.7 . . ?
C2 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 114.7(2) . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
N4 C3 C2 113.9(2) . . ?
N4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
N4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
N4 C4 C5 108.9(2) . . ?
N4 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
N4 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N3 C5 C4 107.5(2) . . ?
N3 C5 H5A 110.2 . . ?
C4 C5 H5A 110.2 . . ?
N3 C5 H5B 110.2 . . ?
C4 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
N3 C6 C7 112.1(2) . . ?
N3 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N3 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 C8 114.8(2) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
N2 C8 C7 111.5(2) . . ?
N2 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N2 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N2 C9 C10 108.0(2) . . ?
N2 C9 H9A 110.1 . . ?
C10 C9 H9A 110.1 . . ?
N2 C9 H9B 110.1 . . ?
C10 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
N1 C10 C9 110.1(2) . . ?
N1 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
N1 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.2 . . ?
N1 C11 C12 118.2(2) . . ?
N1 C11 H11A 107.8 . . ?
C12 C11 H11A 107.8 . . ?
N1 C11 H11B 107.8 . . ?
C12 C11 H11B 107.8 . . ?
H11A C11 H11B 107.1 . . ?
C17 C12 C13 116.6(2) . . ?
C17 C12 C11 120.3(3) . . ?
C13 C12 C11 122.9(2) . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 C18 116.1(3) . . ?
C12 C13 C18 122.9(2) . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 119.5(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 122.3(3) . . ?
C16 C17 H17 118.9 . . ?
C12 C17 H17 118.9 . . ?
F3 C18 F2 106.4(2) . . ?
F3 C18 F1 105.8(2) . . ?
F2 C18 F1 105.1(3) . . ?
F3 C18 C13 113.5(3) . . ?
F2 C18 C13 112.9(2) . . ?
F1 C18 C13 112.5(3) . . ?
C10 N1 C1 109.4(2) . . ?
C10 N1 C11 110.4(2) . . ?
C1 N1 C11 113.7(2) . . ?
C10 N1 Cu1 103.02(15) . . ?
C1 N1 Cu1 108.02(16) . . ?
C11 N1 Cu1 111.81(15) . . ?
C9 N2 C8 110.1(2) . . ?
C9 N2 Cu1 106.66(16) . . ?
C8 N2 Cu1 117.03(17) . . ?
C9 N2 H2N 107.6 . . ?
C8 N2 H2N 107.6 . . ?
Cu1 N2 H2N 107.6 . . ?
C6 N3 C5 111.4(2) . . ?
C6 N3 Cu1 117.81(17) . . ?
C5 N3 Cu1 106.71(16) . . ?
C6 N3 H3N 106.8 . . ?
C5 N3 H3N 106.8 . . ?
Cu1 N3 H3N 106.8 . . ?
C3 N4 C4 109.1(2) . . ?
C3 N4 Cu1 118.31(17) . . ?
C4 N4 Cu1 107.11(16) . . ?
C3 N4 H4N 107.3 . . ?
C4 N4 H4N 107.3 . . ?
Cu1 N4 H4N 107.3 . . ?
N2 Cu1 N4 175.42(9) . . ?
N2 Cu1 N3 92.54(9) . . ?
N4 Cu1 N3 86.16(9) . . ?
N2 Cu1 N1 86.71(8) . . ?
N4 Cu1 N1 94.42(9) . . ?
N3 Cu1 N1 177.67(9) . . ?
O4 Cl1 O3 110.26(13) . . ?
O4 Cl1 O2 109.79(13) . . ?
O3 Cl1 O2 109.98(12) . . ?
O4 Cl1 O1 109.01(12) . . ?
O3 Cl1 O1 108.91(12) . . ?
O2 Cl1 O1 108.85(11) . . ?
O8 Cl2 O7 109.84(12) . . ?
O8 Cl2 O6 109.90(13) . . ?
O7 Cl2 O6 109.90(12) . . ?
O8 Cl2 O5 108.74(12) . . ?
O7 Cl2 O5 109.75(12) . . ?
O6 Cl2 O5 108.68(12) . . ?

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
N1 C1 C2 C3 73.0(3) . . . . ?
C1 C2 C3 N4 -60.8(3) . . . . ?
N4 C4 C5 N3 54.1(3) . . . . ?
N3 C6 C7 C8 -66.9(3) . . . . ?
C6 C7 C8 N2 68.5(3) . . . . ?
N2 C9 C10 N1 -57.5(3) . . . . ?
N1 C11 C12 C17 -68.3(3) . . . . ?
N1 C11 C12 C13 117.9(3) . . . . ?
C17 C12 C13 C14 1.4(4) . . . . ?
C11 C12 C13 C14 175.4(3) . . . . ?
C17 C12 C13 C18 -174.4(3) . . . . ?
C11 C12 C13 C18 -0.3(4) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C18 C13 C14 C15 176.1(3) . . . . ?
C13 C14 C15 C16 -1.1(4) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C15 C16 C17 C12 0.8(4) . . . . ?
C13 C12 C17 C16 -1.8(4) . . . . ?
C11 C12 C17 C16 -176.0(3) . . . . ?
C14 C13 C18 F3 -122.9(3) . . . . ?
C12 C13 C18 F3 53.0(4) . . . . ?
C14 C13 C18 F2 -1.7(4) . . . . ?
C12 C13 C18 F2 174.2(3) . . . . ?
C14 C13 C18 F1 117.0(3) . . . . ?
C12 C13 C18 F1 -67.1(4) . . . . ?
C9 C10 N1 C1 155.2(2) . . . . ?
C9 C10 N1 C11 -79.0(3) . . . . ?
C9 C10 N1 Cu1 40.5(2) . . . . ?
C2 C1 N1 C10 -177.4(2) . . . . ?
C2 C1 N1 C11 58.7(3) . . . . ?
C2 C1 N1 Cu1 -66.0(2) . . . . ?
C12 C11 N1 C10 -60.7(3) . . . . ?
C12 C11 N1 C1 62.6(3) . . . . ?
C12 C11 N1 Cu1 -174.76(19) . . . . ?
C10 C9 N2 C8 170.0(2) . . . . ?
C10 C9 N2 Cu1 42.1(2) . . . . ?
C7 C8 N2 C9 178.6(2) . . . . ?
C7 C8 N2 Cu1 -59.4(3) . . . . ?
C7 C6 N3 C5 -179.7(2) . . . . ?
C7 C6 N3 Cu1 56.6(3) . . . . ?
C4 C5 N3 C6 -171.7(2) . . . . ?
C4 C5 N3 Cu1 -41.9(2) . . . . ?
C2 C3 N4 C4 174.4(2) . . . . ?
C2 C3 N4 Cu1 51.7(3) . . . . ?
C5 C4 N4 C3 -167.4(2) . . . . ?
C5 C4 N4 Cu1 -38.3(2) . . . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.083

