# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_best
_database_code_depnum_ccdc_archive 'CCDC 894907'
_audit_update_record             
;
2012-08-06 deposited with the CCDC.
2015-10-07 downloaded from the CCDC.
;
#TrackingRef '100304D.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 Cu F4 N4 O5'
_chemical_formula_sum            'C14 H14 Cu F4 N4 O5'
_chemical_formula_weight         457.83

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Imma '
_symmetry_space_group_name_Hall  '-I 2b 2 '

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

_cell_length_a                   6.6111(17)
_cell_length_b                   10.9920(13)
_cell_length_c                   20.658(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1501.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    1586
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      26.69

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.026
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             924
_exptl_absorpt_coefficient_mu    1.545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6716
_exptl_absorpt_correction_T_max  0.7275
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex CCD '
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4836
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_sigmaI/netI    0.0765
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         26.99
_reflns_number_total             938
_reflns_number_gt                560
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.04P)²+0.55P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         938
_refine_ls_number_parameters     86
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5000 1.1871(5) 0.3635(3) 0.0448(14) Uani 1 2 d S . .
C2 C 0.5000 1.1221(5) 0.3059(3) 0.0487(14) Uani 1 2 d S . .
C3 C 0.5000 1.1878(5) 0.2482(3) 0.0392(12) Uani 1 2 d S . .
C4 C 0.5000 0.9867(6) 0.3016(3) 0.0475(14) Uani 1 2 d S . .
C5 C 1.0000 0.7500 0.3752(4) 0.0428(18) Uani 1 4 d S . .
H5A H 1.0000 0.6792 0.3472 0.051 Uiso 0.50 2 calc SPR . .
H5B H 1.0000 0.8208 0.3472 0.051 Uiso 0.50 2 calc SPR . .
C6 C 0.8162(6) 0.6375(4) 0.4540(2) 0.0516(11) Uani 1 1 d . . .
H6A H 0.8255 0.5663 0.4264 0.062 Uiso 1 1 calc R . .
H6B H 0.6950 0.6293 0.4801 0.062 Uiso 1 1 calc R . .
C7 C 1.0000 0.7500 0.5468(4) 0.049(2) Uani 1 4 d S . .
H7A H 1.1197 0.7500 0.5740 0.059 Uiso 0.50 2 calc SPR . .
H7B H 0.8803 0.7500 0.5740 0.059 Uiso 0.50 2 calc SPR . .
Cu1 Cu 0.5000 0.7500 0.35225(6) 0.0436(3) Uani 1 4 d S . .
F1 F 0.5000 1.1320(3) 0.41923(17) 0.0515(9) Uani 1 2 d S . .
F2 F 0.5000 1.1392(3) 0.19264(16) 0.0405(7) Uani 1 2 d S . .
N1 N 0.7956(7) 0.7500 0.4114(2) 0.0455(12) Uani 1 2 d S . .
N2 N 1.0000 0.6404(5) 0.4988(2) 0.0461(12) Uani 1 2 d S . .
O1 O 0.5000 0.9254(3) 0.3527(2) 0.0420(8) Uani 1 2 d S . .
O2 O 0.5000 0.9667(4) 0.2461(2) 0.0526(11) Uani 1 2 d S . .
O1W O 0.5000 0.7500 0.2675(3) 0.0525(15) Uani 1 4 d S . .
H1X H 0.6186 0.7912 0.2521 0.063 Uiso 0.25 1 d PR . .
H1Y H 0.3814 0.7088 0.2521 0.063 Uiso 0.25 1 d PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.058(3) 0.041(3) 0.035(4) -0.009(2) 0.000 0.000
C2 0.065(3) 0.035(3) 0.046(4) 0.001(3) 0.000 0.000
C3 0.051(3) 0.032(3) 0.034(3) 0.000(2) 0.000 0.000
C4 0.054(3) 0.042(3) 0.046(4) 0.003(3) 0.000 0.000
C5 0.043(4) 0.040(5) 0.045(5) 0.000 0.000 0.000
C6 0.048(2) 0.048(3) 0.058(3) 0.011(2) -0.003(2) -0.0119(18)
C7 0.039(4) 0.057(6) 0.051(6) 0.000 0.000 0.000
Cu1 0.0512(6) 0.0354(6) 0.0442(6) 0.000 0.000 0.000
F1 0.056(2) 0.048(2) 0.050(2) 0.0121(17) 0.000 0.000
F2 0.0476(16) 0.0277(16) 0.0463(19) -0.0140(14) 0.000 0.000
N1 0.056(3) 0.040(3) 0.040(3) 0.000 -0.010(2) 0.000
N2 0.039(3) 0.063(3) 0.036(3) -0.005(2) 0.000 0.000
O1 0.059(2) 0.029(2) 0.038(2) 0.0030(18) 0.000 0.000
O2 0.053(2) 0.049(3) 0.056(3) -0.016(2) 0.000 0.000
O1W 0.045(3) 0.055(4) 0.058(4) 0.000 0.000 0.000

_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 F1 1.301(7) . ?
C1 C1 1.383(12) 11_585 ?
C1 C2 1.387(8) . ?
C2 C3 1.394(9) . ?
C2 C4 1.491(9) . ?
C3 F2 1.266(6) . ?
C3 C3 1.366(11) 11_585 ?
C4 O2 1.168(7) . ?
C4 O1 1.252(7) . ?
C5 N1 1.544(6) 10_755 ?
C5 N1 1.544(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N1 1.523(5) . ?
C6 N2 1.527(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.561(8) . ?
C7 N2 1.561(8) 11_575 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
Cu1 O1W 1.750(6) . ?
Cu1 O1 1.928(4) . ?
Cu1 O1 1.928(4) 11_575 ?
Cu1 N1 2.305(5) . ?
Cu1 N1 2.305(5) 10_655 ?
N1 C6 1.523(5) 11_575 ?
N2 C6 1.527(5) 10_755 ?
O1W H1X 0.9600 . ?
O1W H1Y 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C1 117.7(3) . 11_585 ?
F1 C1 C2 121.3(5) . . ?
C1 C1 C2 121.0(4) 11_585 . ?
C1 C2 C3 117.8(6) . . ?
C1 C2 C4 124.3(6) . . ?
C3 C2 C4 117.9(6) . . ?
F2 C3 C3 115.0(3) . 11_585 ?
F2 C3 C2 123.8(6) . . ?
C3 C3 C2 121.2(4) 11_585 . ?
O2 C4 O1 136.6(6) . . ?
O2 C4 C2 104.2(6) . . ?
O1 C4 C2 119.2(6) . . ?
N1 C5 N1 122.1(7) 10_755 . ?
N1 C5 H5A 106.8 10_755 . ?
N1 C5 H5A 106.8 . . ?
N1 C5 H5B 106.8 10_755 . ?
N1 C5 H5B 106.8 . . ?
H5A C5 H5B 106.7 . . ?
N1 C6 N2 113.8(4) . . ?
N1 C6 H6A 108.8 . . ?
N2 C6 H6A 108.8 . . ?
N1 C6 H6B 108.8 . . ?
N2 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
N2 C7 N2 101.0(7) . 11_575 ?
N2 C7 H7A 111.6 . . ?
N2 C7 H7A 111.6 11_575 . ?
N2 C7 H7B 111.6 . . ?
N2 C7 H7B 111.6 11_575 . ?
H7A C7 H7B 109.4 . . ?
O1W Cu1 O1 90.29(13) . . ?
O1W Cu1 O1 90.29(13) . 11_575 ?
O1 Cu1 O1 179.4(3) . 11_575 ?
O1W Cu1 N1 122.03(13) . . ?
O1 Cu1 N1 89.85(7) . . ?
O1 Cu1 N1 89.85(7) 11_575 . ?
O1W Cu1 N1 122.03(13) . 10_655 ?
O1 Cu1 N1 89.85(7) . 10_655 ?
O1 Cu1 N1 89.85(7) 11_575 10_655 ?
N1 Cu1 N1 115.9(3) . 10_655 ?
C6 N1 C6 108.6(5) 11_575 . ?
C6 N1 C5 101.6(3) 11_575 . ?
C6 N1 C5 101.6(3) . . ?
C6 N1 Cu1 112.4(2) 11_575 . ?
C6 N1 Cu1 112.4(2) . . ?
C5 N1 Cu1 119.0(4) . . ?
C6 N2 C6 105.4(5) . 10_755 ?
C6 N2 C7 113.7(3) . . ?
C6 N2 C7 113.7(3) 10_755 . ?
C4 O1 Cu1 122.3(4) . . ?
Cu1 O1W H1X 109.5 . . ?
Cu1 O1W H1Y 109.5 . . ?
H1X O1W H1Y 141.1 . . ?


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
F1 C1 C2 C3 180.000(3) . . . . ?
C1 C1 C2 C3 0.000(3) 11_585 . . . ?
F1 C1 C2 C4 0.000(4) . . . . ?
C1 C1 C2 C4 180.000(3) 11_585 . . . ?
C1 C2 C3 F2 180.000(2) . . . . ?
C4 C2 C3 F2 0.000(3) . . . . ?
C1 C2 C3 C3 0.000(4) . . . 11_585 ?
C4 C2 C3 C3 180.000(2) . . . 11_585 ?
C1 C2 C4 O2 180.000(3) . . . . ?
C3 C2 C4 O2 0.000(3) . . . . ?
C1 C2 C4 O1 0.000(3) . . . . ?
C3 C2 C4 O1 180.000(2) . . . . ?
N2 C6 N1 C6 -49.3(6) . . . 11_575 ?
N2 C6 N1 C5 57.3(5) . . . . ?
N2 C6 N1 Cu1 -174.3(3) . . . . ?
N1 C5 N1 C6 56.0(3) 10_755 . . 11_575 ?
N1 C5 N1 C6 -56.0(3) 10_755 . . . ?
N1 C5 N1 Cu1 180.0 10_755 . . . ?
O1W Cu1 N1 C6 118.5(3) . . . 11_575 ?
O1 Cu1 N1 C6 28.3(3) . . . 11_575 ?
O1 Cu1 N1 C6 -151.2(3) 11_575 . . 11_575 ?
N1 Cu1 N1 C6 -61.5(3) 10_655 . . 11_575 ?
O1W Cu1 N1 C6 -118.5(3) . . . . ?
O1 Cu1 N1 C6 151.2(3) . . . . ?
O1 Cu1 N1 C6 -28.3(3) 11_575 . . . ?
N1 Cu1 N1 C6 61.5(3) 10_655 . . . ?
O1W Cu1 N1 C5 0.000(1) . . . . ?
O1 Cu1 N1 C5 -90.25(11) . . . . ?
O1 Cu1 N1 C5 90.25(11) 11_575 . . . ?
N1 Cu1 N1 C5 180.0 10_655 . . . ?
N1 C6 N2 C6 -65.3(6) . . . 10_755 ?
N1 C6 N2 C7 59.8(5) . . . . ?
N2 C7 N2 C6 -60.3(3) 11_575 . . . ?
N2 C7 N2 C6 60.3(3) 11_575 . . 10_755 ?
O2 C4 O1 Cu1 0.000(3) . . . . ?
C2 C4 O1 Cu1 180.000(2) . . . . ?
O1W Cu1 O1 C4 0.000(2) . . . . ?
N1 Cu1 O1 C4 122.03(13) . . . . ?
N1 Cu1 O1 C4 -122.03(13) 10_655 . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.089


