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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Cu250k_a
_database_code_depnum_ccdc_archive 'CCDC 1533040'
_audit_update_record             
;
2017-02-16 deposited with the CCDC.
2017-03-28 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            'C12 H13 Cu F6 N2 O2 P'
_chemical_formula_weight         425.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   8.8221(2)
_cell_length_b                   19.4655(4)
_cell_length_c                   8.7295(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1499.09(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    10414
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      27.46

_exptl_crystal_description       pillar
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.886
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    1.641
_shelx_estimated_absorpt_T_min   0.532
_shelx_estimated_absorpt_T_max   0.746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7495
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13587
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.135
_diffrn_reflns_theta_max         27.457
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1715
_reflns_number_gt                1504
_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       'RAPID-AUTO (Rigaku, 2002)'
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2002)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2002)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Yadokari-XG (Wakita, Nemoto et al., 2009) and ORTEP-3
 for Windows (Farrugia ,1997))
;
_computing_publication_material  
;
Yadokari-XG (Wakita, Nemoto et al., 2009) and publCIF
(Westrip, 2010)
;
_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)+(0.0470P)²+0.2901P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1715
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.5000 0.5000 0.02725(12) Uani 1 2 d S . P . .
O1 O 0.51836(12) 0.41576(5) 0.38681(12) 0.0329(3) Uani 1 1 d . . . . .
H1 H 0.5000 0.4207(16) 0.2500 0.049 Uiso 1 2 d S U P . .
N1 N 0.35405(13) 0.44730(6) 0.62171(13) 0.0296(3) Uani 1 1 d . . . . .
C1 C 0.4521(2) 0.35787(7) 0.45844(19) 0.0350(3) Uani 1 1 d . . . . .
H2 H 0.5321 0.3266 0.4933 0.042 Uiso 1 1 calc R U . . .
H3 H 0.3888 0.3332 0.3844 0.042 Uiso 1 1 calc R U . . .
C2 C 0.35668(16) 0.37956(7) 0.59322(16) 0.0306(3) Uani 1 1 d . . . . .
C3 C 0.27497(19) 0.33365(9) 0.68320(19) 0.0395(4) Uani 1 1 d . . . . .
H4 H 0.2777 0.2863 0.6623 0.047 Uiso 1 1 calc R U . . .
C4 C 0.1902(2) 0.35850(10) 0.8032(2) 0.0447(4) Uani 1 1 d . . . . .
H5 H 0.1370 0.3281 0.8673 0.054 Uiso 1 1 calc R U . . .
C5 C 0.18366(19) 0.42898(9) 0.82913(19) 0.0421(4) Uani 1 1 d . . . . .
H6 H 0.1240 0.4468 0.9090 0.050 Uiso 1 1 calc R U . . .
C6 C 0.2658(2) 0.47199(9) 0.73616(16) 0.0353(3) Uani 1 1 d . . . . .
H7 H 0.2606 0.5197 0.7523 0.042 Uiso 1 1 calc R U . . .
P1 P 0.0000 0.65007(3) 0.7500 0.03402(16) Uani 1 2 d S T P . .
F1 F -0.04573(17) 0.59214(6) 0.62891(14) 0.0608(3) Uani 1 1 d . . . . .
F2 F 0.16876(13) 0.65021(6) 0.68411(15) 0.0582(3) Uani 1 1 d . . . . .
F3 F 0.04537(15) 0.70809(6) 0.87074(13) 0.0573(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 Cu1 0.0000 5_666 ?
Cu1 O1 1.9213(11) 5_666 ?
Cu1 O1 1.9213(10) . ?
Cu1 N1 1.9594(12) 5_666 ?
Cu1 N1 1.9594(12) . ?
O1 C1 1.4150(18) . ?
O1 Cu1 1.9213(10) 5_666 ?
O1 H1 1.209(3) . ?
N1 C2 1.3419(19) . ?
N1 C6 1.3549(19) . ?
N1 Cu1 1.9594(12) 5_666 ?
C1 C2 1.507(2) . ?
C1 H2 0.9800 . ?
C1 H3 0.9800 . ?
C2 C3 1.391(2) . ?
C3 C4 1.375(3) . ?
C3 H4 0.9400 . ?
C4 C5 1.392(3) . ?
C4 H5 0.9400 . ?
C5 C6 1.373(2) . ?
C5 H6 0.9400 . ?
C6 H7 0.9400 . ?
P1 F3 1.5957(11) 4_556 ?
P1 F3 1.5958(11) . ?
P1 F2 1.5961(11) . ?
P1 F2 1.5961(11) 4_556 ?
P1 F1 1.5974(12) . ?
P1 F1 1.5974(12) 4_556 ?

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
Cu1 Cu1 O1 0(10) 5_666 5_666 ?
Cu1 Cu1 O1 0(10) 5_666 . ?
O1 Cu1 O1 180.00(3) 5_666 . ?
Cu1 Cu1 N1 0(10) 5_666 5_666 ?
O1 Cu1 N1 83.54(5) 5_666 5_666 ?
O1 Cu1 N1 96.46(5) . 5_666 ?
Cu1 Cu1 N1 0(10) 5_666 . ?
O1 Cu1 N1 96.46(5) 5_666 . ?
O1 Cu1 N1 83.54(5) . . ?
N1 Cu1 N1 180.00(6) 5_666 . ?
C1 O1 Cu1 114.68(9) . 5_666 ?
C1 O1 Cu1 114.68(9) . . ?
Cu1 O1 Cu1 0.0 5_666 . ?
C1 O1 H1 116.4(13) . . ?
Cu1 O1 H1 115.4(15) 5_666 . ?
Cu1 O1 H1 115.4(15) . . ?
C2 N1 C6 119.68(13) . . ?
C2 N1 Cu1 113.74(9) . 5_666 ?
C6 N1 Cu1 126.29(11) . 5_666 ?
C2 N1 Cu1 113.74(9) . . ?
C6 N1 Cu1 126.29(11) . . ?
Cu1 N1 Cu1 0.0 5_666 . ?
O1 C1 C2 110.65(12) . . ?
O1 C1 H2 109.5 . . ?
C2 C1 H2 109.5 . . ?
O1 C1 H3 109.5 . . ?
C2 C1 H3 109.5 . . ?
H2 C1 H3 108.1 . . ?
N1 C2 C3 121.17(14) . . ?
N1 C2 C1 115.44(12) . . ?
C3 C2 C1 123.38(14) . . ?
C4 C3 C2 119.08(15) . . ?
C4 C3 H4 120.5 . . ?
C2 C3 H4 120.5 . . ?
C3 C4 C5 119.54(15) . . ?
C3 C4 H5 120.2 . . ?
C5 C4 H5 120.2 . . ?
C6 C5 C4 118.90(16) . . ?
C6 C5 H6 120.6 . . ?
C4 C5 H6 120.6 . . ?
N1 C6 C5 121.53(16) . . ?
N1 C6 H7 119.2 . . ?
C5 C6 H7 119.2 . . ?
F3 P1 F3 89.90(9) 4_556 . ?
F3 P1 F2 89.69(7) 4_556 . ?
F3 P1 F2 90.16(7) . . ?
F3 P1 F2 90.16(7) 4_556 4_556 ?
F3 P1 F2 89.69(7) . 4_556 ?
F2 P1 F2 179.80(10) . 4_556 ?
F3 P1 F1 89.95(7) 4_556 . ?
F3 P1 F1 179.84(8) . . ?
F2 P1 F1 89.91(7) . . ?
F2 P1 F1 90.24(7) 4_556 . ?
F3 P1 F1 179.84(8) 4_556 4_556 ?
F3 P1 F1 89.96(7) . 4_556 ?
F2 P1 F1 90.24(7) . 4_556 ?
F2 P1 F1 89.91(7) 4_556 4_556 ?
F1 P1 F1 90.19(10) . 4_556 ?

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 C2 10.91(16) 5_666 . . . ?
Cu1 O1 C1 C2 10.91(16) . . . . ?
C6 N1 C2 C3 -2.6(2) . . . . ?
Cu1 N1 C2 C3 171.52(11) 5_666 . . . ?
Cu1 N1 C2 C3 171.52(11) . . . . ?
C6 N1 C2 C1 176.94(14) . . . . ?
Cu1 N1 C2 C1 -8.89(16) 5_666 . . . ?
Cu1 N1 C2 C1 -8.89(16) . . . . ?
O1 C1 C2 N1 -1.14(19) . . . . ?
O1 C1 C2 C3 178.44(14) . . . . ?
N1 C2 C3 C4 0.0(2) . . . . ?
C1 C2 C3 C4 -179.51(16) . . . . ?
C2 C3 C4 C5 2.1(3) . . . . ?
C3 C4 C5 C6 -1.7(3) . . . . ?
C2 N1 C6 C5 3.1(2) . . . . ?
Cu1 N1 C6 C5 -170.29(12) 5_666 . . . ?
Cu1 N1 C6 C5 -170.29(12) . . . . ?
C4 C5 C6 N1 -0.9(3) . . . . ?

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
C1 H2 F3 0.98 2.60 3.3766(19) 136.5 6_657
C1 H3 F2 0.98 2.63 3.465(2) 142.9 8_565
C5 H6 F1 0.94 2.55 3.334(2) 141.0 8_566
C6 H7 O1 0.94 2.62 3.091(2) 111.6 5_666
C6 H7 F1 0.94 2.58 3.260(2) 129.4 4_556
C1 H2 F3 0.98 2.60 3.3766(19) 136.5 6_657

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.086


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water and acetonitrile'
_exptl_crystal_preparation       ', Magnetic properties'
####################################################################### 
# 
# 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_Cu150k_a
_database_code_depnum_ccdc_archive 'CCDC 1533043'
_audit_update_record             
;
2017-02-16 deposited with the CCDC.
2017-03-28 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            'C12 H13 Cu F6 N2 O2 P'
_chemical_formula_weight         425.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   8.7142(2)
_cell_length_b                   19.3795(4)
_cell_length_c                   8.7366(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1475.41(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11212
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      27.44

_exptl_crystal_description       pillar
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    1.667
_shelx_estimated_absorpt_T_min   0.527
_shelx_estimated_absorpt_T_max   0.742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7628
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13397
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.140
_diffrn_reflns_theta_max         27.444
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1689
_reflns_number_gt                1546
_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       'RAPID-AUTO (Rigaku, 2002)'
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2002)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2002)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Yadokari-XG (Wakita, Nemoto et al., 2009) and ORTEP-3
 for Windows (Farrugia ,1997))
;
_computing_publication_material  
;
Yadokari-XG (Wakita, Nemoto et al., 2009) and publCIF
(Westrip, 2010)
;
_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)+(0.0480P)²+0.4176P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1689
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0740
_refine_ls_wR_factor_gt          0.0721
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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 0.01589(11) Uani 1 2 d S . P . .
O1 O 0.48159(11) 0.58459(5) 0.38676(11) 0.0196(2) Uani 1 1 d . . . . .
H1 H 0.5000 0.5793(15) 0.2500 0.029 Uiso 1 2 d S U P . .
N1 N 0.64697(13) 0.55303(6) 0.62248(12) 0.0180(2) Uani 1 1 d . . . . .
C1 C 0.54851(17) 0.64303(7) 0.45852(17) 0.0211(3) Uani 1 1 d . . . . .
H2 H 0.4666 0.6748 0.4930 0.025 Uiso 1 1 calc R U . . .
H3 H 0.6138 0.6679 0.3840 0.025 Uiso 1 1 calc R U . . .
C2 C 0.64427(15) 0.62119(7) 0.59404(15) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.72593(16) 0.66754(7) 0.68487(16) 0.0232(3) Uani 1 1 d . . . . .
H4 H 0.7231 0.7156 0.6637 0.028 Uiso 1 1 calc R U . . .
C4 C 0.81111(18) 0.64249(8) 0.80617(18) 0.0263(3) Uani 1 1 d . . . . .
H5 H 0.8649 0.6734 0.8714 0.032 Uiso 1 1 calc R U . . .
C5 C 0.81747(16) 0.57143(8) 0.83217(16) 0.0248(3) Uani 1 1 d . . . . .
H6 H 0.8775 0.5532 0.9135 0.030 Uiso 1 1 calc R U . . .
C6 C 0.73505(17) 0.52817(8) 0.73774(14) 0.0210(3) Uani 1 1 d . . . . .
H7 H 0.7401 0.4797 0.7539 0.025 Uiso 1 1 calc R U . . .
P1 P 1.0000 0.34999(3) 0.7500 0.01934(14) Uani 1 2 d S T P . .
F1 F 0.95206(13) 0.40847(5) 0.87106(11) 0.0344(2) Uani 1 1 d . . . . .
F2 F 0.82889(10) 0.34980(5) 0.68245(11) 0.0323(2) Uani 1 1 d . . . . .
F3 F 1.04751(12) 0.29152(5) 0.62895(10) 0.0320(2) 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 Cu1 0.0000 5_666 ?
Cu1 O1 1.9214(10) 5_666 ?
Cu1 O1 1.9214(10) . ?
Cu1 N1 1.9600(11) 5_666 ?
Cu1 N1 1.9600(11) . ?
O1 C1 1.4198(16) . ?
O1 Cu1 1.9214(10) 5_666 ?
O1 H1 1.210(3) . ?
N1 C2 1.3443(17) . ?
N1 C6 1.3546(18) . ?
N1 Cu1 1.9600(11) 5_666 ?
C1 C2 1.5090(19) . ?
C1 H2 0.9900 . ?
C1 H3 0.9900 . ?
C2 C3 1.3939(19) . ?
C3 C4 1.382(2) . ?
C3 H4 0.9500 . ?
C4 C5 1.397(2) . ?
C4 H5 0.9500 . ?
C5 C6 1.378(2) . ?
C5 H6 0.9500 . ?
C6 H7 0.9500 . ?
P1 F2 1.6036(9) . ?
P1 F2 1.6037(9) 4_756 ?
P1 F3 1.6043(9) . ?
P1 F3 1.6043(9) 4_756 ?
P1 F1 1.6054(9) 4_756 ?
P1 F1 1.6054(9) . ?

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
Cu1 Cu1 O1 0(10) 5_666 5_666 ?
Cu1 Cu1 O1 0(10) 5_666 . ?
O1 Cu1 O1 180.0 5_666 . ?
Cu1 Cu1 N1 0(10) 5_666 5_666 ?
O1 Cu1 N1 83.59(4) 5_666 5_666 ?
O1 Cu1 N1 96.41(4) . 5_666 ?
Cu1 Cu1 N1 0(10) 5_666 . ?
O1 Cu1 N1 96.41(4) 5_666 . ?
O1 Cu1 N1 83.59(4) . . ?
N1 Cu1 N1 180.00(6) 5_666 . ?
C1 O1 Cu1 114.76(8) . 5_666 ?
C1 O1 Cu1 114.76(8) . . ?
Cu1 O1 Cu1 0.0 5_666 . ?
C1 O1 H1 116.7(12) . . ?
Cu1 O1 H1 115.2(13) 5_666 . ?
Cu1 O1 H1 115.2(13) . . ?
C2 N1 C6 119.79(12) . . ?
C2 N1 Cu1 113.76(9) . 5_666 ?
C6 N1 Cu1 126.13(10) . 5_666 ?
C2 N1 Cu1 113.76(9) . . ?
C6 N1 Cu1 126.13(10) . . ?
Cu1 N1 Cu1 0.0 5_666 . ?
O1 C1 C2 110.48(11) . . ?
O1 C1 H2 109.6 . . ?
C2 C1 H2 109.6 . . ?
O1 C1 H3 109.6 . . ?
C2 C1 H3 109.6 . . ?
H2 C1 H3 108.1 . . ?
N1 C2 C3 121.27(12) . . ?
N1 C2 C1 115.48(11) . . ?
C3 C2 C1 123.25(12) . . ?
C4 C3 C2 118.97(13) . . ?
C4 C3 H4 120.5 . . ?
C2 C3 H4 120.5 . . ?
C3 C4 C5 119.50(13) . . ?
C3 C4 H5 120.3 . . ?
C5 C4 H5 120.3 . . ?
C6 C5 C4 118.79(13) . . ?
C6 C5 H6 120.6 . . ?
C4 C5 H6 120.6 . . ?
N1 C6 C5 121.60(13) . . ?
N1 C6 H7 119.2 . . ?
C5 C6 H7 119.2 . . ?
F2 P1 F2 179.73(8) . 4_756 ?
F2 P1 F3 89.75(5) . . ?
F2 P1 F3 90.06(5) 4_756 . ?
F2 P1 F3 90.06(5) . 4_756 ?
F2 P1 F3 89.75(5) 4_756 4_756 ?
F3 P1 F3 90.13(7) . 4_756 ?
F2 P1 F1 90.07(5) . 4_756 ?
F2 P1 F1 90.12(5) 4_756 4_756 ?
F3 P1 F1 89.84(5) . 4_756 ?
F3 P1 F1 179.87(6) 4_756 4_756 ?
F2 P1 F1 90.12(5) . . ?
F2 P1 F1 90.07(5) 4_756 . ?
F3 P1 F1 179.87(6) . . ?
F3 P1 F1 89.84(5) 4_756 . ?
F1 P1 F1 90.20(8) 4_756 . ?

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 C2 10.66(14) 5_666 . . . ?
Cu1 O1 C1 C2 10.66(14) . . . . ?
C6 N1 C2 C3 -2.57(19) . . . . ?
Cu1 N1 C2 C3 171.24(10) 5_666 . . . ?
Cu1 N1 C2 C3 171.24(10) . . . . ?
C6 N1 C2 C1 177.18(12) . . . . ?
Cu1 N1 C2 C1 -9.01(14) 5_666 . . . ?
Cu1 N1 C2 C1 -9.01(14) . . . . ?
O1 C1 C2 N1 -0.89(16) . . . . ?
O1 C1 C2 C3 178.85(12) . . . . ?
N1 C2 C3 C4 0.1(2) . . . . ?
C1 C2 C3 C4 -179.66(13) . . . . ?
C2 C3 C4 C5 2.0(2) . . . . ?
C3 C4 C5 C6 -1.6(2) . . . . ?
C2 N1 C6 C5 3.0(2) . . . . ?
Cu1 N1 C6 C5 -169.96(11) 5_666 . . . ?
Cu1 N1 C6 C5 -169.96(11) . . . . ?
C4 C5 C6 N1 -0.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 1.210(3) 1.210(3) 2.411(2) 170(3) 4_655
C1 H2 F3 0.99 2.56 3.3464(16) 136.6 7_765
C1 H3 F2 0.99 2.59 3.4361(18) 142.8 8_565
C5 H6 F1 0.95 2.51 3.3027(17) 141.0 5_767
C6 H7 O1 0.95 2.61 3.0858(18) 111.6 5_666
C6 H7 F1 0.95 2.52 3.2116(17) 129.4 .
O1 H1 O1 1.210(3) 1.210(3) 2.411(2) 170(3) 4_655
C1 H2 F3 0.99 2.56 3.3464(16) 136.6 7_765

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.106


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water and acetonitrile'
_exptl_crystal_preparation       ', Magnetic properties'
####################################################################### 
# 
# 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_Cu300k_a
_database_code_depnum_ccdc_archive 'CCDC 1533041'
_audit_update_record             
;
2017-02-16 deposited with the CCDC.
2017-03-28 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            'C12 H13 Cu F6 N2 O2 P'
_chemical_formula_weight         425.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   8.8886(4)
_cell_length_b                   19.5247(8)
_cell_length_c                   8.7308(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1515.21(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9767
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      27.46

_exptl_crystal_description       pillar
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    1.623
_shelx_estimated_absorpt_T_min   0.535
_shelx_estimated_absorpt_T_max   0.748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7567
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13770
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.130
_diffrn_reflns_theta_max         27.455
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1735
_reflns_number_gt                1472
_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       'RAPID-AUTO (Rigaku, 2002)'
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2002)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2002)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Yadokari-XG (Wakita, Nemoto et al., 2009) and ORTEP-3
 for Windows (Farrugia ,1997))
;
_computing_publication_material  
;
Yadokari-XG (Wakita, Nemoto et al., 2009) and publCIF
(Westrip, 2010)
;
_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)+(0.0506P)²+0.2078P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1735
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_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 0.03444(13) Uani 1 2 d S . P . .
O1 O 0.51858(14) 0.58409(6) 0.61325(13) 0.0412(3) Uani 1 1 d . . . . .
H1 H 0.5000 0.5800(17) 0.7500 0.062 Uiso 1 2 d S U P . .
N1 N 0.35463(15) 0.55258(7) 0.37868(15) 0.0373(3) Uani 1 1 d . . . . .
C1 C 0.4524(2) 0.64162(8) 0.5415(2) 0.0440(4) Uani 1 1 d . . . . .
H2 H 0.5308 0.6725 0.5066 0.053 Uiso 1 1 calc R U . . .
H3 H 0.3905 0.6660 0.6149 0.053 Uiso 1 1 calc R U . . .
C2 C 0.35725(18) 0.62000(8) 0.40727(18) 0.0380(3) Uani 1 1 d . . . . .
C3 C 0.2757(2) 0.66559(10) 0.3177(2) 0.0505(4) Uani 1 1 d . . . . .
H4 H 0.2784 0.7123 0.3383 0.061 Uiso 1 1 calc R U . . .
C4 C 0.1911(2) 0.64083(11) 0.1984(2) 0.0563(5) Uani 1 1 d . . . . .
H5 H 0.1385 0.6708 0.1353 0.068 Uiso 1 1 calc R U . . .
C5 C 0.1846(2) 0.57088(11) 0.1727(2) 0.0530(5) Uani 1 1 d . . . . .
H6 H 0.1254 0.5533 0.0942 0.064 Uiso 1 1 calc R U . . .
C6 C 0.2666(2) 0.52795(10) 0.26496(18) 0.0443(4) Uani 1 1 d . . . . .
H7 H 0.2616 0.4809 0.2489 0.053 Uiso 1 1 calc R U . . .
P1 P 0.0000 0.34984(3) 0.2500 0.04361(19) Uani 1 2 d S T P . .
F1 F -0.0443(2) 0.40753(7) 0.37107(16) 0.0777(4) Uani 1 1 d . . . . .
F2 F 0.16721(15) 0.34976(8) 0.31496(18) 0.0758(4) Uani 1 1 d . . . . .
F3 F 0.04386(18) 0.29214(7) 0.12959(16) 0.0741(4) 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 1.9236(11) 5_666 ?
Cu1 O1 1.9236(11) . ?
Cu1 N1 1.9609(13) 5_666 ?
Cu1 N1 1.9609(13) . ?
O1 C1 1.415(2) . ?
O1 H1 1.208(3) . ?
N1 C2 1.340(2) . ?
N1 C6 1.353(2) . ?
C1 C2 1.505(2) . ?
C1 H2 0.9700 . ?
C1 H3 0.9700 . ?
C2 C3 1.389(2) . ?
C3 C4 1.372(3) . ?
C3 H4 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H5 0.9300 . ?
C5 C6 1.372(3) . ?
C5 H6 0.9300 . ?
C6 H7 0.9300 . ?
P1 F3 1.5896(13) . ?
P1 F3 1.5896(13) 4 ?
P1 F2 1.5908(12) . ?
P1 F2 1.5908(12) 4 ?
P1 F1 1.5941(14) . ?
P1 F1 1.5941(14) 4 ?

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(4) 5_666 . ?
O1 Cu1 N1 83.54(5) 5_666 5_666 ?
O1 Cu1 N1 96.46(5) . 5_666 ?
O1 Cu1 N1 96.46(5) 5_666 . ?
O1 Cu1 N1 83.54(5) . . ?
N1 Cu1 N1 180.0 5_666 . ?
C1 O1 Cu1 114.47(10) . . ?
C1 O1 H1 115.7(14) . . ?
Cu1 O1 H1 116.1(16) . . ?
C2 N1 C6 119.74(15) . . ?
C2 N1 Cu1 113.72(10) . . ?
C6 N1 Cu1 126.27(12) . . ?
O1 C1 C2 110.85(14) . . ?
O1 C1 H2 109.5 . . ?
C2 C1 H2 109.5 . . ?
O1 C1 H3 109.5 . . ?
C2 C1 H3 109.5 . . ?
H2 C1 H3 108.1 . . ?
N1 C2 C3 121.04(16) . . ?
N1 C2 C1 115.48(14) . . ?
C3 C2 C1 123.48(15) . . ?
C4 C3 C2 119.17(17) . . ?
C4 C3 H4 120.4 . . ?
C2 C3 H4 120.4 . . ?
C3 C4 C5 119.55(17) . . ?
C3 C4 H5 120.2 . . ?
C5 C4 H5 120.2 . . ?
C6 C5 C4 119.01(18) . . ?
C6 C5 H6 120.5 . . ?
C4 C5 H6 120.5 . . ?
N1 C6 C5 121.40(18) . . ?
N1 C6 H7 119.3 . . ?
C5 C6 H7 119.3 . . ?
F3 P1 F3 89.73(11) . 4 ?
F3 P1 F2 90.34(8) . . ?
F3 P1 F2 89.58(8) 4 . ?
F3 P1 F2 89.58(8) . 4 ?
F3 P1 F2 90.34(8) 4 4 ?
F2 P1 F2 179.89(12) . 4 ?
F3 P1 F1 179.81(9) . . ?
F3 P1 F1 90.09(8) 4 . ?
F2 P1 F1 89.72(9) . . ?
F2 P1 F1 90.36(9) 4 . ?
F3 P1 F1 90.09(8) . 4 ?
F3 P1 F1 179.81(9) 4 4 ?
F2 P1 F1 90.36(9) . 4 ?
F2 P1 F1 89.72(9) 4 4 ?
F1 P1 F1 90.09(12) . 4 ?

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 C2 10.95(19) . . . . ?
C6 N1 C2 C3 -2.7(2) . . . . ?
Cu1 N1 C2 C3 171.61(13) . . . . ?
C6 N1 C2 C1 176.86(15) . . . . ?
Cu1 N1 C2 C1 -8.79(18) . . . . ?
O1 C1 C2 N1 -1.2(2) . . . . ?
O1 C1 C2 C3 178.34(16) . . . . ?
N1 C2 C3 C4 0.1(3) . . . . ?
C1 C2 C3 C4 -179.42(19) . . . . ?
C2 C3 C4 C5 2.1(3) . . . . ?
C3 C4 C5 C6 -1.8(3) . . . . ?
C2 N1 C6 C5 3.1(3) . . . . ?
Cu1 N1 C6 C5 -170.51(14) . . . . ?
C4 C5 C6 N1 -0.8(3) . . . . ?

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
C1 H2 F3 0.97 2.62 3.395(2) 136.6 6_666
C5 H6 F1 0.93 2.58 3.355(2) 141.1 8_565
C6 H7 O1 0.93 2.62 3.092(2) 111.9 5_666
C6 H7 F1 0.93 2.62 3.293(2) 129.4 4
C1 H2 F3 0.97 2.62 3.395(2) 136.6 6_666

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.084


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water and acetonitrile'
_exptl_crystal_preparation       ', Magnetic properties'
####################################################################### 
# 
# 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_Cu200k_a
_database_code_depnum_ccdc_archive 'CCDC 1533042'
_audit_update_record             
;
2017-02-16 deposited with the CCDC.
2017-03-28 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            'C12 H13 Cu F6 N2 O2 P'
_chemical_formula_weight         425.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   8.7671(2)
_cell_length_b                   19.4257(4)
_cell_length_c                   8.7330(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1487.29(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    10794
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.46

_exptl_crystal_description       pillar
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    1.654
_shelx_estimated_absorpt_T_min   0.530
_shelx_estimated_absorpt_T_max   0.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7782
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13444
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.137
_diffrn_reflns_theta_max         27.461
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1699
_reflns_number_gt                1527
_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       'RAPID-AUTO (Rigaku, 2002)'
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2002)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2002)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Yadokari-XG (Wakita, Nemoto et al., 2009) and ORTEP-3
 for Windows (Farrugia ,1997))
;
_computing_publication_material  
;
Yadokari-XG (Wakita, Nemoto et al., 2009) and publCIF
(Westrip, 2010)
;
_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)+(0.0480P)²+0.3357P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1699
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0769
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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 0.02150(12) Uani 1 2 d S . P . .
O1 O 0.51840(12) 0.58440(5) 0.61327(12) 0.0263(2) Uani 1 1 d . . . . .
H1 H 0.5000 0.5801(15) 0.7500 0.040 Uiso 1 2 d S U P . .
N1 N 0.35347(13) 0.55290(6) 0.37784(13) 0.0234(2) Uani 1 1 d . . . . .
C1 C 0.45179(19) 0.64255(7) 0.54160(18) 0.0279(3) Uani 1 1 d . . . . .
H2 H 0.5331 0.6742 0.5068 0.033 Uiso 1 1 calc R U . . .
H3 H 0.3872 0.6675 0.6163 0.033 Uiso 1 1 calc R U . . .
C2 C 0.35612(16) 0.62083(7) 0.40644(15) 0.0245(3) Uani 1 1 d . . . . .
C3 C 0.27450(18) 0.66698(8) 0.31613(17) 0.0313(3) Uani 1 1 d . . . . .
H4 H 0.2772 0.7149 0.3374 0.038 Uiso 1 1 calc R U . . .
C4 C 0.18954(19) 0.64197(9) 0.1952(2) 0.0352(4) Uani 1 1 d . . . . .
H5 H 0.1359 0.6728 0.1301 0.042 Uiso 1 1 calc R U . . .
C5 C 0.18312(18) 0.57121(9) 0.16933(17) 0.0337(3) Uani 1 1 d . . . . .
H6 H 0.1230 0.5531 0.0883 0.040 Uiso 1 1 calc R U . . .
C6 C 0.26531(18) 0.52811(8) 0.26302(15) 0.0282(3) Uani 1 1 d . . . . .
H7 H 0.2602 0.4798 0.2469 0.034 Uiso 1 1 calc R U . . .
P1 P 0.0000 0.34995(3) 0.2500 0.02652(15) Uani 1 2 d S T P . .
F1 F -0.04691(15) 0.40817(5) 0.37112(12) 0.0473(3) Uani 1 1 d . . . . .
F2 F 0.16995(11) 0.34981(6) 0.31673(13) 0.0448(3) Uani 1 1 d . . . . .
F3 F 0.04638(14) 0.29172(5) 0.12911(12) 0.0445(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 Cu1 0.0000 5_666 ?
Cu1 O1 1.9216(10) 5_666 ?
Cu1 O1 1.9216(10) . ?
Cu1 N1 1.9607(11) 5_666 ?
Cu1 N1 1.9607(11) . ?
O1 C1 1.4173(17) . ?
O1 Cu1 1.9216(10) 5_666 ?
O1 H1 1.208(2) . ?
N1 C2 1.3432(18) . ?
N1 C6 1.3545(18) . ?
N1 Cu1 1.9607(11) 5_666 ?
C1 C2 1.508(2) . ?
C1 H2 0.9900 . ?
C1 H3 0.9900 . ?
C2 C3 1.392(2) . ?
C3 C4 1.381(2) . ?
C3 H4 0.9500 . ?
C4 C5 1.394(2) . ?
C4 H5 0.9500 . ?
C5 C6 1.375(2) . ?
C5 H6 0.9500 . ?
C6 H7 0.9500 . ?
P1 F2 1.5998(10) 4 ?
P1 F3 1.5999(10) 4 ?
P1 F2 1.5999(10) . ?
P1 F3 1.5999(10) . ?
P1 F1 1.6022(10) . ?
P1 F1 1.6022(10) 4 ?

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
Cu1 Cu1 O1 0(10) 5_666 5_666 ?
Cu1 Cu1 O1 0(10) 5_666 . ?
O1 Cu1 O1 180.00(3) 5_666 . ?
Cu1 Cu1 N1 0(10) 5_666 5_666 ?
O1 Cu1 N1 83.56(5) 5_666 5_666 ?
O1 Cu1 N1 96.44(5) . 5_666 ?
Cu1 Cu1 N1 0(10) 5_666 . ?
O1 Cu1 N1 96.44(5) 5_666 . ?
O1 Cu1 N1 83.56(5) . . ?
N1 Cu1 N1 180.0 5_666 . ?
C1 O1 Cu1 114.72(9) . 5_666 ?
C1 O1 Cu1 114.72(9) . . ?
Cu1 O1 Cu1 0.0 5_666 . ?
C1 O1 H1 115.9(12) . . ?
Cu1 O1 H1 116.0(14) 5_666 . ?
Cu1 O1 H1 116.0(14) . . ?
C2 N1 C6 119.78(12) . . ?
C2 N1 Cu1 113.73(9) . 5_666 ?
C6 N1 Cu1 126.18(10) . 5_666 ?
C2 N1 Cu1 113.73(9) . . ?
C6 N1 Cu1 126.18(10) . . ?
Cu1 N1 Cu1 0.0 5_666 . ?
O1 C1 C2 110.59(11) . . ?
O1 C1 H2 109.5 . . ?
C2 C1 H2 109.5 . . ?
O1 C1 H3 109.5 . . ?
C2 C1 H3 109.5 . . ?
H2 C1 H3 108.1 . . ?
N1 C2 C3 121.23(13) . . ?
N1 C2 C1 115.47(12) . . ?
C3 C2 C1 123.30(13) . . ?
C4 C3 C2 118.95(14) . . ?
C4 C3 H4 120.5 . . ?
C2 C3 H4 120.5 . . ?
C3 C4 C5 119.51(14) . . ?
C3 C4 H5 120.2 . . ?
C5 C4 H5 120.2 . . ?
C6 C5 C4 118.88(14) . . ?
C6 C5 H6 120.6 . . ?
C4 C5 H6 120.6 . . ?
N1 C6 C5 121.55(15) . . ?
N1 C6 H7 119.2 . . ?
C5 C6 H7 119.2 . . ?
F2 P1 F3 90.14(6) 4 4 ?
F2 P1 F2 179.80(9) 4 . ?
F3 P1 F2 89.72(6) 4 . ?
F2 P1 F3 89.72(6) 4 . ?
F3 P1 F3 90.00(8) 4 . ?
F2 P1 F3 90.14(6) . . ?
F2 P1 F1 90.15(6) 4 . ?
F3 P1 F1 89.90(6) 4 . ?
F2 P1 F1 89.99(6) . . ?
F3 P1 F1 179.84(7) . . ?
F2 P1 F1 89.99(6) 4 4 ?
F3 P1 F1 179.84(7) 4 4 ?
F2 P1 F1 90.15(6) . 4 ?
F3 P1 F1 89.90(6) . 4 ?
F1 P1 F1 90.20(9) . 4 ?

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 C2 10.78(15) 5_666 . . . ?
Cu1 O1 C1 C2 10.78(15) . . . . ?
C6 N1 C2 C3 -2.6(2) . . . . ?
Cu1 N1 C2 C3 171.38(11) 5_666 . . . ?
Cu1 N1 C2 C3 171.38(11) . . . . ?
C6 N1 C2 C1 177.06(13) . . . . ?
Cu1 N1 C2 C1 -8.91(15) 5_666 . . . ?
Cu1 N1 C2 C1 -8.91(15) . . . . ?
O1 C1 C2 N1 -1.04(18) . . . . ?
O1 C1 C2 C3 178.66(13) . . . . ?
N1 C2 C3 C4 0.0(2) . . . . ?
C1 C2 C3 C4 -179.68(15) . . . . ?
C2 C3 C4 C5 2.2(2) . . . . ?
C3 C4 C5 C6 -1.7(2) . . . . ?
C2 N1 C6 C5 3.1(2) . . . . ?
Cu1 N1 C6 C5 -170.11(11) 5_666 . . . ?
Cu1 N1 C6 C5 -170.11(11) . . . . ?
C4 C5 C6 N1 -0.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H2 F3 0.99 2.57 3.3625(17) 136.5 6_666
C1 H3 F2 0.99 2.61 3.450(2) 142.8 8_566
C5 H6 F1 0.95 2.53 3.3181(19) 140.9 8_565
C6 H7 O1 0.95 2.61 3.0888(19) 111.5 5_666
C6 H7 F1 0.95 2.55 3.2353(19) 129.4 4
C1 H2 F3 0.99 2.57 3.3625(17) 136.5 6_666

_refine_diff_density_max         0.476
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.098


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water and acetonitrile'
_exptl_crystal_preparation       ', Magnetic properties'
####################################################################### 
# 
# 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_Cu100k_a
_database_code_depnum_ccdc_archive 'CCDC 1533039'
_audit_update_record             
;
2017-02-16 deposited with the CCDC.
2017-03-28 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            'C12 H13 Cu F6 N2 O2 P'
_chemical_formula_weight         425.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   8.6711(2)
_cell_length_b                   19.3370(4)
_cell_length_c                   8.7396(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1465.40(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11192
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      27.43

_exptl_crystal_description       pillar
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    1.679
_shelx_estimated_absorpt_T_min   0.525
_shelx_estimated_absorpt_T_max   0.741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7687
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13321
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.142
_diffrn_reflns_theta_max         27.439
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1683
_reflns_number_gt                1547
_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       'RAPID-AUTO (Rigaku, 2002)'
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2002)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2002)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Yadokari-XG (Wakita, Nemoto et al., 2009) and ORTEP-3
 for Windows (Farrugia ,1997))
;
_computing_publication_material  
;
Yadokari-XG (Wakita, Nemoto et al., 2009) and publCIF
(Westrip, 2010)
;
_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)+(0.0426P)²+0.5792P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1683
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0686
_refine_ls_wR_factor_gt          0.0672
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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 0.01092(10) Uani 1 2 d S . P . .
O1 O 0.51837(11) 0.41524(5) 0.38676(11) 0.0140(2) Uani 1 1 d . . . . .
H1 H 0.5000 0.4206(14) 0.2500 0.021 Uiso 1 2 d S U P . .
N1 N 0.35268(13) 0.44682(6) 0.62298(12) 0.0127(2) Uani 1 1 d . . . . .
C1 C 0.45116(16) 0.35656(7) 0.45854(16) 0.0149(3) Uani 1 1 d . . . . .
H2 H 0.5335 0.3247 0.4927 0.018 Uiso 1 1 calc R U . . .
H3 H 0.3853 0.3317 0.3842 0.018 Uiso 1 1 calc R U . . .
C2 C 0.35519(15) 0.37852(7) 0.59446(15) 0.0131(3) Uani 1 1 d . . . . .
C3 C 0.27372(16) 0.33196(7) 0.68564(15) 0.0164(3) Uani 1 1 d . . . . .
H4 H 0.2768 0.2838 0.6645 0.020 Uiso 1 1 calc R U . . .
C4 C 0.18844(17) 0.35704(7) 0.80732(16) 0.0183(3) Uani 1 1 d . . . . .
H5 H 0.1346 0.3261 0.8727 0.022 Uiso 1 1 calc R U . . .
C5 C 0.18209(16) 0.42842(7) 0.83323(16) 0.0176(3) Uani 1 1 d . . . . .
H6 H 0.1220 0.4467 0.9146 0.021 Uiso 1 1 calc R U . . .
C6 C 0.26471(17) 0.47171(7) 0.73830(14) 0.0149(3) Uani 1 1 d . . . . .
H7 H 0.2597 0.5202 0.7543 0.018 Uiso 1 1 calc R U . . .
P1 P 0.0000 0.64998(3) 0.7500 0.01304(13) Uani 1 2 d S T P . .
F1 F -0.04873(11) 0.59119(4) 0.62901(10) 0.0232(2) Uani 1 1 d . . . . .
F2 F 0.17204(10) 0.65021(4) 0.68179(10) 0.0217(2) Uani 1 1 d . . . . .
F3 F 0.04840(11) 0.70866(4) 0.87116(10) 0.0218(2) 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 1.9213(10) 5_666 ?
Cu1 O1 1.9213(10) . ?
Cu1 N1 1.9607(11) 5_666 ?
Cu1 N1 1.9607(11) . ?
O1 C1 1.4214(16) . ?
O1 H1 1.210(3) . ?
N1 C2 1.3443(16) . ?
N1 C6 1.3525(17) . ?
C1 C2 1.5113(18) . ?
C1 H2 0.9900 . ?
C1 H3 0.9900 . ?
C2 C3 1.3944(18) . ?
C3 C4 1.383(2) . ?
C3 H4 0.9500 . ?
C4 C5 1.3997(19) . ?
C4 H5 0.9500 . ?
C5 C6 1.3792(19) . ?
C5 H6 0.9500 . ?
C6 H7 0.9500 . ?
P1 F2 1.6065(8) 4_556 ?
P1 F2 1.6065(8) . ?
P1 F3 1.6076(9) . ?
P1 F3 1.6077(9) 4_556 ?
P1 F1 1.6090(9) . ?
P1 F1 1.6090(9) 4_556 ?

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(3) 5_666 . ?
O1 Cu1 N1 83.62(4) 5_666 5_666 ?
O1 Cu1 N1 96.38(4) . 5_666 ?
O1 Cu1 N1 96.38(4) 5_666 . ?
O1 Cu1 N1 83.62(4) . . ?
N1 Cu1 N1 180.00(5) 5_666 . ?
C1 O1 Cu1 114.81(8) . . ?
C1 O1 H1 116.7(11) . . ?
Cu1 O1 H1 115.2(13) . . ?
C2 N1 C6 119.79(12) . . ?
C2 N1 Cu1 113.78(9) . . ?
C6 N1 Cu1 126.11(9) . . ?
O1 C1 C2 110.40(11) . . ?
O1 C1 H2 109.6 . . ?
C2 C1 H2 109.6 . . ?
O1 C1 H3 109.6 . . ?
C2 C1 H3 109.6 . . ?
H2 C1 H3 108.1 . . ?
N1 C2 C3 121.35(12) . . ?
N1 C2 C1 115.50(11) . . ?
C3 C2 C1 123.15(12) . . ?
C4 C3 C2 118.93(12) . . ?
C4 C3 H4 120.5 . . ?
C2 C3 H4 120.5 . . ?
C3 C4 C5 119.42(13) . . ?
C3 C4 H5 120.3 . . ?
C5 C4 H5 120.3 . . ?
C6 C5 C4 118.73(13) . . ?
C6 C5 H6 120.6 . . ?
C4 C5 H6 120.6 . . ?
N1 C6 C5 121.68(13) . . ?
N1 C6 H7 119.2 . . ?
C5 C6 H7 119.2 . . ?
F2 P1 F2 179.69(7) 4_556 . ?
F2 P1 F3 89.77(5) 4_556 . ?
F2 P1 F3 90.00(5) . . ?
F2 P1 F3 90.01(5) 4_556 4_556 ?
F2 P1 F3 89.77(5) . 4_556 ?
F3 P1 F3 90.22(7) . 4_556 ?
F2 P1 F1 90.11(5) 4_556 . ?
F2 P1 F1 90.11(5) . . ?
F3 P1 F1 179.87(5) . . ?
F3 P1 F1 89.84(5) 4_556 . ?
F2 P1 F1 90.11(5) 4_556 4_556 ?
F2 P1 F1 90.11(5) . 4_556 ?
F3 P1 F1 89.84(5) . 4_556 ?
F3 P1 F1 179.87(5) 4_556 4_556 ?
F1 P1 F1 90.10(7) . 4_556 ?

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 C2 10.55(14) . . . . ?
C6 N1 C2 C3 -2.76(19) . . . . ?
Cu1 N1 C2 C3 171.11(10) . . . . ?
C6 N1 C2 C1 177.20(12) . . . . ?
Cu1 N1 C2 C1 -8.93(14) . . . . ?
O1 C1 C2 N1 -0.87(16) . . . . ?
O1 C1 C2 C3 179.09(12) . . . . ?
N1 C2 C3 C4 0.2(2) . . . . ?
C1 C2 C3 C4 -179.71(13) . . . . ?
C2 C3 C4 C5 1.9(2) . . . . ?
C3 C4 C5 C6 -1.6(2) . . . . ?
C2 N1 C6 C5 3.1(2) . . . . ?
Cu1 N1 C6 C5 -169.94(10) . . . . ?
C4 C5 C6 N1 -0.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H2 F3 0.99 2.54 3.3326(15) 136.7 6_657
C1 H3 F2 0.99 2.58 3.4242(17) 142.8 8_565
C3 H4 F2 0.95 2.63 3.5460(16) 163.4 7_655
C5 H6 F1 0.95 2.50 3.2912(16) 141.1 8_566
C6 H7 O1 0.95 2.60 3.0841(17) 111.7 5_666
C6 H7 F1 0.95 2.50 3.1922(16) 129.4 4_556
C1 H2 F3 0.99 2.54 3.3326(15) 136.7 6_657

_refine_diff_density_max         0.503
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.100


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water and acetonitrile'
_exptl_crystal_preparation       ', Magnetic properties'
