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

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

data_1a
_database_code_depnum_ccdc_archive 'CCDC 1427126'
_audit_update_record             
;
2016-04-05 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 Cu N4, C3 F5 O2'
_chemical_formula_sum            'C27 H16 Cu F5 N4 O2'
_chemical_formula_weight         586.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  -P2yn

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

_cell_length_a                   12.346(3)
_cell_length_b                   9.3473(19)
_cell_length_c                   20.554(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.01(3)
_cell_angle_gamma                90.00
_cell_volume                     2342.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    21857
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    1.008
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_T_max  0.817
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Weissenberg IP'
_diffrn_measurement_method       'scintillation counter'
_diffrn_detector_area_resol_mean None
_diffrn_standards_number         None
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        'not measured'
_diffrn_reflns_number            21857
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5343
_reflns_number_gt                4486
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'TEXRAY software (Molecular Structure Corporation, 1999)'
_computing_cell_refinement       'TEXRAY software'
_computing_data_reduction        
'TEXSAN (Molecular Structure Corporation, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  "SHELXL-97/2 (Sheldrick,1997)')"

_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)+(0.0840P)²+1.1110P] 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         5343
_refine_ls_number_parameters     371
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1411
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.150
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.77182(2) 0.71280(3) 0.025796(13) 0.03400(8) Uani 1 1 d . . .
N1 N 0.93376(15) 0.73162(19) 0.01185(9) 0.0297(4) Uani 1 1 d . . .
N2 N 0.81080(14) 0.8851(2) 0.08302(8) 0.0314(4) Uani 1 1 d . . .
N3 N 0.68603(14) 0.6112(2) -0.05200(9) 0.0323(4) Uani 1 1 d . . .
N4 N 0.70406(15) 0.5554(2) 0.07708(9) 0.0324(4) Uani 1 1 d . . .
C1 C 0.7078(2) 0.5326(3) 0.14129(11) 0.0416(6) Uani 1 1 d . . .
H1 H 0.7456 0.6001 0.1712 0.050 Uiso 1 1 calc R . .
C2 C 0.6593(2) 0.4150(3) 0.16707(13) 0.0497(6) Uani 1 1 d . . .
H2 H 0.6653 0.4026 0.2134 0.060 Uiso 1 1 calc R . .
C3 C 0.6030(2) 0.3176(3) 0.12488(13) 0.0425(6) Uani 1 1 d . . .
H3 H 0.5685 0.2377 0.1415 0.051 Uiso 1 1 calc R . .
C4 C 0.59692(17) 0.3376(2) 0.05693(11) 0.0337(5) Uani 1 1 d . . .
C5 C 0.54364(18) 0.2384(3) 0.00921(13) 0.0377(5) Uani 1 1 d . . .
H5 H 0.5089 0.1561 0.0236 0.045 Uiso 1 1 calc R . .
C6 C 0.54207(18) 0.2600(3) -0.05592(13) 0.0380(5) Uani 1 1 d . . .
H6 H 0.5086 0.1911 -0.0866 0.046 Uiso 1 1 calc R . .
C7 C 0.59052(17) 0.3863(2) -0.07930(11) 0.0346(5) Uani 1 1 d . . .
C8 C 0.5903(2) 0.4155(3) -0.14654(12) 0.0439(6) Uani 1 1 d . . .
H8 H 0.5582 0.3496 -0.1792 0.053 Uiso 1 1 calc R . .
C9 C 0.6364(2) 0.5392(3) -0.16446(12) 0.0471(6) Uani 1 1 d . . .
H9 H 0.6373 0.5596 -0.2097 0.057 Uiso 1 1 calc R . .
C10 C 0.6824(2) 0.6360(3) -0.11579(11) 0.0420(6) Uani 1 1 d . . .
H10 H 0.7122 0.7229 -0.1291 0.050 Uiso 1 1 calc R . .
C11 C 0.64148(16) 0.4871(2) -0.03373(10) 0.0302(4) Uani 1 1 d . . .
C12 C 0.64729(17) 0.4602(2) 0.03555(10) 0.0297(4) Uiso 1 1 d . . .
C13 C 0.99054(18) 0.6629(2) -0.02830(11) 0.0342(5) Uani 1 1 d . . .
H13 H 0.9546 0.5906 -0.0562 0.041 Uiso 1 1 calc R . .
C14 C 1.10084(19) 0.6920(3) -0.03141(12) 0.0395(5) Uani 1 1 d . . .
H14 H 1.1379 0.6422 -0.0617 0.047 Uiso 1 1 calc R . .
C15 C 1.15460(19) 0.7930(2) 0.00963(12) 0.0385(5) Uani 1 1 d . . .
H15 H 1.2302 0.8114 0.0094 0.046 Uiso 1 1 calc R . .
C16 C 1.09711(17) 0.8695(2) 0.05227(11) 0.0331(5) Uani 1 1 d . . .
C17 C 1.1461(2) 0.9761(3) 0.09757(12) 0.0415(6) Uani 1 1 d . . .
H17 H 1.2217 0.9980 0.0998 0.050 Uiso 1 1 calc R . .
C18 C 1.0861(2) 1.0457(3) 0.13710(12) 0.0413(6) Uani 1 1 d . . .
H18 H 1.1210 1.1145 0.1674 0.050 Uiso 1 1 calc R . .
C19 C 0.97086(19) 1.0184(2) 0.13463(10) 0.0342(5) Uani 1 1 d . . .
C20 C 0.9036(2) 1.0914(3) 0.17343(11) 0.0405(6) Uani 1 1 d . . .
H20 H 0.9338 1.1629 0.2038 0.049 Uiso 1 1 calc R . .
C21 C 0.7953(2) 1.0584(3) 0.16692(11) 0.0422(6) Uani 1 1 d . . .
H21 H 0.7499 1.1052 0.1935 0.051 Uiso 1 1 calc R . .
C22 C 0.7508(2) 0.9554(3) 0.12101(11) 0.0381(5) Uani 1 1 d . . .
H22 H 0.6747 0.9348 0.1168 0.046 Uiso 1 1 calc R . .
C23 C 0.92034(17) 0.9152(2) 0.09058(10) 0.0288(4) Uani 1 1 d . . .
C24 C 0.98524(16) 0.8363(2) 0.05035(10) 0.0280(4) Uani 1 1 d . . .
F1 F 1.13333(17) 0.3824(2) 0.22715(11) 0.0824(6) Uani 1 1 d . . .
F4 F 0.9971(2) 0.7054(2) 0.21741(12) 0.0995(8) Uani 1 1 d D . .
F5 F 1.11775(17) 0.6188(2) 0.15537(9) 0.0751(6) Uani 1 1 d D . .
O2 O 0.93429(19) 0.3573(3) 0.28371(11) 0.0670(6) Uani 1 1 d . . .
O3 O 1.0223(3) 0.5298(2) 0.34375(12) 0.0797(8) Uani 1 1 d . . .
C26 C 0.9986(3) 0.4567(3) 0.29510(14) 0.0571(7) Uani 1 1 d D . .
F2A F 1.1789(3) 0.5711(6) 0.27738(18) 0.0717(12) Uani 0.50 1 d PD A 1
F3A F 0.9555(3) 0.5196(7) 0.15950(19) 0.0948(19) Uani 0.50 1 d PD A 1
C25A C 1.0375(5) 0.5877(7) 0.1951(3) 0.0625(13) Uani 0.50 1 d PD A 1
C28A C 1.0898(5) 0.4951(6) 0.2506(3) 0.0499(11) Uani 0.50 1 d PD A 1
F2B F 0.9792(5) 0.4362(6) 0.1747(2) 0.1095(18) Uani 0.50 1 d PD A 2
F3B F 1.1756(4) 0.6536(5) 0.2565(2) 0.0762(13) Uani 0.50 1 d PD A 2
C25B C 1.0895(5) 0.6135(7) 0.2152(3) 0.0625(13) Uani 0.50 1 d PD A 2
C28B C 1.0467(5) 0.4690(6) 0.2274(3) 0.0499(11) Uani 0.50 1 d PD A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 2.0077(18) . ?
Cu1 N3 2.0124(19) . ?
Cu1 N4 2.0622(19) . ?
Cu1 N1 2.0712(19) . ?
N1 C13 1.329(3) . ?
N1 C24 1.353(3) . ?
N2 C22 1.331(3) . ?
N2 C23 1.366(3) . ?
N3 C10 1.325(3) . ?
N3 C11 1.362(3) . ?
N4 C1 1.330(3) . ?
N4 C12 1.351(3) . ?
C1 C2 1.396(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.369(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(3) . ?
C3 H3 0.9500 . ?
C4 C12 1.406(3) . ?
C4 C5 1.433(3) . ?
C5 C6 1.351(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.440(3) . ?
C6 H6 0.9500 . ?
C7 C11 1.406(3) . ?
C7 C8 1.408(3) . ?
C8 C9 1.365(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.401(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.437(3) . ?
C13 C14 1.400(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.367(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.406(3) . ?
C15 H15 0.9500 . ?
C16 C24 1.410(3) . ?
C16 C17 1.431(3) . ?
C17 C18 1.349(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.439(3) . ?
C18 H18 0.9500 . ?
C19 C23 1.401(3) . ?
C19 C20 1.414(3) . ?
C20 C21 1.357(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.399(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.441(3) . ?
F1 C28A 1.308(6) . ?
F1 C28B 1.342(6) . ?
F4 C25A 1.319(7) . ?
F4 C25B 1.434(7) . ?
F5 C25B 1.331(6) . ?
F5 C25A 1.409(6) . ?
O2 C26 1.221(4) . ?
O3 C26 1.209(4) . ?
C26 C28A 1.599(6) . ?
C26 C28B 1.601(6) . ?
F2A C28A 1.352(7) . ?
F3A C25A 1.316(7) . ?
C25A C28A 1.496(8) . ?
F2B C28B 1.295(6) . ?
F3B C25B 1.306(7) . ?
C25B C28B 1.486(8) . ?

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 N3 153.13(7) . . ?
N2 Cu1 N4 110.62(7) . . ?
N3 Cu1 N4 82.20(7) . . ?
N2 Cu1 N1 82.24(7) . . ?
N3 Cu1 N1 109.23(7) . . ?
N4 Cu1 N1 127.51(7) . . ?
C13 N1 C24 117.88(19) . . ?
C13 N1 Cu1 131.25(16) . . ?
C24 N1 Cu1 110.84(14) . . ?
C22 N2 C23 117.62(19) . . ?
C22 N2 Cu1 129.44(16) . . ?
C23 N2 Cu1 111.96(14) . . ?
C10 N3 C11 118.0(2) . . ?
C10 N3 Cu1 129.49(17) . . ?
C11 N3 Cu1 111.59(14) . . ?
C1 N4 C12 117.1(2) . . ?
C1 N4 Cu1 131.83(16) . . ?
C12 N4 Cu1 111.04(14) . . ?
N4 C1 C2 123.5(2) . . ?
N4 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C3 C2 C1 119.3(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C12 117.6(2) . . ?
C3 C4 C5 123.0(2) . . ?
C12 C4 C5 119.4(2) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 120.7(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C11 C7 C8 117.1(2) . . ?
C11 C7 C6 119.5(2) . . ?
C8 C7 C6 123.3(2) . . ?
C9 C8 C7 119.5(2) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 119.6(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
N3 C10 C9 122.8(2) . . ?
N3 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
N3 C11 C7 123.03(19) . . ?
N3 C11 C12 117.57(18) . . ?
C7 C11 C12 119.4(2) . . ?
N4 C12 C4 123.39(19) . . ?
N4 C12 C11 116.84(19) . . ?
C4 C12 C11 119.76(19) . . ?
N1 C13 C14 123.1(2) . . ?
N1 C13 H13 118.5 . . ?
C14 C13 H13 118.5 . . ?
C15 C14 C13 119.2(2) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 119.5(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C24 117.3(2) . . ?
C15 C16 C17 123.8(2) . . ?
C24 C16 C17 118.9(2) . . ?
C18 C17 C16 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 121.8(2) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C23 C19 C20 117.1(2) . . ?
C23 C19 C18 118.9(2) . . ?
C20 C19 C18 124.1(2) . . ?
C21 C20 C19 119.4(2) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 120.0(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
N2 C22 C21 122.6(2) . . ?
N2 C22 H22 118.7 . . ?
C21 C22 H22 118.7 . . ?
N2 C23 C19 123.2(2) . . ?
N2 C23 C24 117.33(18) . . ?
C19 C23 C24 119.45(19) . . ?
N1 C24 C16 122.94(19) . . ?
N1 C24 C23 116.94(18) . . ?
C16 C24 C23 120.13(19) . . ?
C28A F1 C28B 30.6(3) . . ?
C25A F4 C25B 31.1(3) . . ?
C25B F5 C25A 31.5(3) . . ?
O3 C26 O2 130.9(3) . . ?
O3 C26 C28A 104.2(3) . . ?
O2 C26 C28A 123.8(3) . . ?
O3 C26 C28B 127.2(3) . . ?
O2 C26 C28B 101.9(3) . . ?
C28A C26 C28B 25.3(3) . . ?
F3A C25A F4 107.3(5) . . ?
F3A C25A F5 109.1(5) . . ?
F4 C25A F5 111.5(5) . . ?
F3A C25A C28A 110.3(5) . . ?
F4 C25A C28A 111.0(5) . . ?
F5 C25A C28A 107.6(5) . . ?
F1 C28A F2A 102.6(4) . . ?
F1 C28A C25A 109.8(5) . . ?
F2A C28A C25A 103.5(5) . . ?
F1 C28A C26 113.4(4) . . ?
F2A C28A C26 119.0(4) . . ?
C25A C28A C26 107.9(4) . . ?
F3B C25B F5 106.6(5) . . ?
F3B C25B F4 112.2(5) . . ?
F5 C25B F4 109.3(4) . . ?
F3B C25B C28B 115.2(5) . . ?
F5 C25B C28B 109.9(5) . . ?
F4 C25B C28B 103.5(5) . . ?
F2B C28B F1 105.3(5) . . ?
F2B C28B C25B 105.9(5) . . ?
F1 C28B C25B 104.1(5) . . ?
F2B C28B C26 115.6(5) . . ?
F1 C28B C26 111.4(4) . . ?
C25B C28B C26 113.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.182
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.112
####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1427127'
_audit_update_record             
;
2016-04-05 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 Cu N4, C5 F7 O3, C6 H6'
_chemical_formula_sum            'C35 H18 Cu F7 N4 O3'
_chemical_formula_weight         739.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Ibam
_symmetry_space_group_name_Hall  -I22c

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

_cell_length_a                   15.422(3)
_cell_length_b                   17.640(4)
_cell_length_c                   21.739(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5914(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      12
_cell_measurement_theta_max      18

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2976
_exptl_absorpt_coefficient_mu    0.829
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.680
_exptl_absorpt_correction_T_max  0.848
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Weissenberg IP'
_diffrn_measurement_method       'scintillation counter'
_diffrn_detector_area_resol_mean None
_diffrn_standards_number         None
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        'not measured'
_diffrn_reflns_number            27606
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3472
_reflns_number_gt                2955
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'TEXRAY software (Molecular Structure Corporation, 1999)'
_computing_cell_refinement       'TEXRAY software'
_computing_data_reduction        
'TEXSAN (Molecular Structure Corporation, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  "SHELXL-97/2 (Sheldrick,1997)')"

_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)+(0.1541P)²+17.4230P] 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         3472
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0731
_refine_ls_wR_factor_ref         0.2262
_refine_ls_wR_factor_gt          0.2181
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.005
_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
Cu1 Cu 0.13202(4) 0.5000 0.2500 0.0237(2) Uani 1 2 d S . .
N1 N 0.09278(17) 0.40153(15) 0.28781(11) 0.0248(6) Uani 1 1 d . . .
N2 N 0.18556(16) 0.42998(14) 0.18597(11) 0.0216(5) Uani 1 1 d . . .
F7 F 0.0671(2) 0.1883(2) 0.5000 0.0511(9) Uani 1 2 d S A .
F5 F 0.0203(3) 0.0966(3) 0.4426(3) 0.0518(12) Uani 0.590(7) 1 d P A 1
F3 F -0.0838(3) 0.1935(3) 0.4401(2) 0.0436(12) Uani 0.590(7) 1 d P . 1
F1 F -0.1339(3) 0.0427(2) 0.4624(2) 0.0457(10) Uani 0.590(7) 1 d P . 1
F2 F -0.1607(4) 0.0810(3) 0.5586(3) 0.0457(10) Uani 0.41 1 d P . 2
F4 F -0.0948(4) 0.2186(3) 0.5317(3) 0.0436(12) Uani 0.41 1 d P . 2
F6 F 0.0368(5) 0.0785(5) 0.5341(4) 0.0518(12) Uani 0.41 1 d P . 2
C1 C -0.2466(5) 0.1378(4) 0.4752(3) 0.090(2) Uani 1 1 d . . .
C2 C -0.1555(3) 0.1008(2) 0.5000 0.0265(9) Uani 1 2 d S . .
C4 C 0.0119(3) 0.1309(3) 0.5000 0.0371(12) Uani 1 2 d S . .
C5 C 0.0520(2) 0.3884(2) 0.34100(15) 0.0356(8) Uani 1 1 d . . .
O1 O -0.2791(4) 0.1829(3) 0.5000 0.080(2) Uani 1 2 d S . .
O2 O -0.2647(4) 0.1181(3) 0.4239(3) 0.1120(19) Uani 1 1 d . . .
C6 C 0.0369(3) 0.3144(3) 0.36263(18) 0.0436(10) Uani 1 1 d . . .
H H 0.0089 0.3073 0.4001 0.052 Uiso 1 1 calc R . .
C7 C 0.0625(2) 0.2539(2) 0.3295(2) 0.0447(10) Uani 1 1 d . . .
C8 C 0.1064(2) 0.2655(2) 0.27328(19) 0.0341(8) Uani 1 1 d . . .
C9 C 0.1362(2) 0.2052(2) 0.2355(3) 0.0426(10) Uani 1 1 d . . .
HA H 0.1264 0.1554 0.2477 0.051 Uiso 1 1 calc R . .
C10 C 0.1786(2) 0.2190(2) 0.1820(2) 0.0440(10) Uani 1 1 d . . .
HB H 0.1963 0.1784 0.1577 0.053 Uiso 1 1 calc R . .
C11 C 0.1971(2) 0.29606(19) 0.16185(17) 0.0309(7) Uani 1 1 d . . .
C12 C 0.2428(2) 0.3138(2) 0.10816(17) 0.0379(8) Uani 1 1 d . . .
HC H 0.2627 0.2756 0.0822 0.046 Uiso 1 1 calc R . .
C13 C 0.2579(2) 0.3890(2) 0.09447(16) 0.0351(8) Uani 1 1 d . . .
HD H 0.2877 0.4021 0.0588 0.042 Uiso 1 1 calc R . .
C14 C 0.2282(2) 0.44587(19) 0.13439(14) 0.0272(7) Uani 1 1 d . . .
HE H 0.2386 0.4963 0.1244 0.033 Uiso 1 1 calc R . .
C15 C 0.16896(19) 0.35590(17) 0.19908(14) 0.0233(6) Uani 1 1 d . . .
C16 C 0.1215(2) 0.3405(2) 0.25482(14) 0.0246(7) Uani 1 1 d . . .
C20 C 0.0449(3) 0.0000(2) 0.1954(2) 0.0444(10) Uani 1 1 d . . .
HF H 0.0749 0.0001 0.1583 0.053 Uiso 1 1 calc R . .
C21 C 0.0899(4) 0.0000 0.2500 0.0393(13) Uani 1 2 d S . .
HG H 0.1502 0.0000 0.2500 0.047 Uiso 1 2 calc SR . .
C17 C 0.0898(4) 0.5012(3) 0.0000 0.0353(12) Uani 1 2 d S . .
HH H 0.1501 0.5017 0.0000 0.042 Uiso 1 2 calc SR . .
C18 C 0.0458(4) 0.4331(3) 0.0000 0.0400(12) Uani 1 2 d S . .
HI H 0.0768 0.3878 0.0000 0.048 Uiso 1 2 calc SR . .
C19 C -0.0442(3) 0.4314(3) 0.0000 0.0380(11) Uani 1 2 d S . .
HJ H -0.0735 0.3853 0.0000 0.046 Uiso 1 2 calc SR . .
C3 C -0.0806(3) 0.1601(3) 0.5000 0.0289(9) Uiso 1 2 d S . .


_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 2.015(3) . ?
Cu1 N1 2.015(3) 8_455 ?
Cu1 N2 2.036(3) 8_455 ?
Cu1 N2 2.036(3) . ?
N1 C5 1.337(4) . ?
N1 C16 1.368(5) . ?
N2 C14 1.330(4) . ?
N2 C15 1.362(4) . ?
F7 C4 1.322(7) . ?
F5 C4 1.392(6) . ?
F3 C3 1.430(4) . ?
F1 C2 1.353(5) . ?
F1 F1 1.634(9) 10_556 ?
F2 C2 1.324(7) . ?
F2 O2 1.773(9) 10_556 ?
F2 C1 1.816(11) 10_556 ?
F4 C3 1.261(8) . ?
F4 F4 1.377(14) 10_556 ?
F6 C4 1.245(10) . ?
F6 F6 1.482(17) 10_556 ?
C1 C1 1.078(14) 10_556 ?
C1 O1 1.084(8) . ?
C1 O2 1.200(8) . ?
C1 C2 1.640(11) . ?
C1 F2 1.816(11) 10_556 ?
C2 F2 1.324(7) 10_556 ?
C2 F1 1.353(5) 10_556 ?
C2 C3 1.557(6) . ?
C2 C1 1.640(11) 10_556 ?
C4 F6 1.245(10) 10_556 ?
C4 F5 1.392(6) 10_556 ?
C4 C3 1.517(7) . ?
C5 C6 1.407(5) . ?
O1 C1 1.084(8) 10_556 ?
O2 F2 1.773(9) 10_556 ?
C6 C7 1.347(7) . ?
C6 H 0.9300 . ?
C7 C8 1.413(6) . ?
C8 C16 1.402(5) . ?
C8 C9 1.419(7) . ?
C9 C10 1.356(7) . ?
C9 HA 0.9300 . ?
C10 C11 1.457(5) . ?
C10 HB 0.9300 . ?
C11 C12 1.399(6) . ?
C11 C15 1.399(5) . ?
C12 C13 1.380(6) . ?
C12 HC 0.9300 . ?
C13 C14 1.403(5) . ?
C13 HD 0.9300 . ?
C14 HE 0.9300 . ?
C15 C16 1.441(4) . ?
C20 C21 1.374(6) . ?
C20 C20 1.386(10) 2 ?
C20 HF 0.9300 . ?
C21 C20 1.374(6) 8_445 ?
C21 HG 0.9300 . ?
C17 C18 1.380(7) . ?
C17 C19 1.382(8) 9_565 ?
C17 HH 0.9300 . ?
C18 C19 1.389(8) . ?
C18 HI 0.9300 . ?
C19 C17 1.382(8) 9_565 ?
C19 HJ 0.9300 . ?
C3 F4 1.261(8) 10_556 ?
C3 F3 1.430(4) 10_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
N1 Cu1 N1 145.04(15) . 8_455 ?
N1 Cu1 N2 111.47(10) . 8_455 ?
N1 Cu1 N2 82.98(10) 8_455 8_455 ?
N1 Cu1 N2 82.98(10) . . ?
N1 Cu1 N2 111.47(10) 8_455 . ?
N2 Cu1 N2 132.14(14) 8_455 . ?
C5 N1 C16 118.0(3) . . ?
C5 N1 Cu1 130.0(3) . . ?
C16 N1 Cu1 111.6(2) . . ?
C14 N2 C15 118.1(3) . . ?
C14 N2 Cu1 130.5(2) . . ?
C15 N2 Cu1 111.3(2) . . ?
C2 F1 F1 52.8(2) . 10_556 ?
C2 F2 O2 99.4(5) . 10_556 ?
C2 F2 C1 60.6(4) . 10_556 ?
O2 F2 C1 39.1(3) 10_556 10_556 ?
C3 F4 F4 56.9(3) . 10_556 ?
C4 F6 F6 53.5(4) . 10_556 ?
C1 C1 O1 60.2(5) 10_556 . ?
C1 C1 O2 158.3(4) 10_556 . ?
O1 C1 O2 124.6(10) . . ?
C1 C1 C2 70.8(2) 10_556 . ?
O1 C1 C2 121.6(6) . . ?
O2 C1 C2 112.9(7) . . ?
C1 C1 F2 113.9(3) 10_556 10_556 ?
O1 C1 F2 160.6(7) . 10_556 ?
O2 C1 F2 68.5(5) . 10_556 ?
C2 C1 F2 44.7(3) . 10_556 ?
F2 C2 F2 148.5(6) 10_556 . ?
F2 C2 F1 39.9(3) 10_556 . ?
F2 C2 F1 113.3(5) . . ?
F2 C2 F1 113.3(5) 10_556 10_556 ?
F2 C2 F1 39.9(3) . 10_556 ?
F1 C2 F1 74.3(5) . 10_556 ?
F2 C2 C3 102.9(3) 10_556 . ?
F2 C2 C3 102.9(3) . . ?
F1 C2 C3 109.0(4) . . ?
F1 C2 C3 109.0(4) 10_556 . ?
F2 C2 C1 74.7(4) 10_556 . ?
F2 C2 C1 111.7(5) . . ?
F1 C2 C1 108.3(3) . . ?
F1 C2 C1 135.3(4) 10_556 . ?
C3 C2 C1 111.6(4) . . ?
F2 C2 C1 111.7(5) 10_556 10_556 ?
F2 C2 C1 74.7(4) . 10_556 ?
F1 C2 C1 135.3(4) . 10_556 ?
F1 C2 C1 108.3(3) 10_556 10_556 ?
C3 C2 C1 111.6(4) . 10_556 ?
C1 C2 C1 38.4(5) . 10_556 ?
F6 C4 F6 73.0(7) . 10_556 ?
F6 C4 F7 111.7(5) . . ?
F6 C4 F7 111.7(5) 10_556 . ?
F6 C4 F5 100.4(6) . . ?
F6 C4 F5 27.8(3) 10_556 . ?
F7 C4 F5 105.8(3) . . ?
F6 C4 F5 27.8(3) . 10_556 ?
F6 C4 F5 100.4(6) 10_556 10_556 ?
F7 C4 F5 105.8(3) . 10_556 ?
F5 C4 F5 127.2(6) . 10_556 ?
F6 C4 C3 122.8(5) . . ?
F6 C4 C3 122.8(5) 10_556 . ?
F7 C4 C3 110.2(5) . . ?
F5 C4 C3 103.6(3) . . ?
F5 C4 C3 103.6(3) 10_556 . ?
N1 C5 C6 121.8(4) . . ?
C1 O1 C1 59.7(9) 10_556 . ?
C1 O2 F2 72.4(6) . 10_556 ?
C7 C6 C5 120.6(4) . . ?
C7 C6 H 119.7 . . ?
C5 C6 H 119.7 . . ?
C6 C7 C8 119.2(3) . . ?
C16 C8 C7 117.6(4) . . ?
C16 C8 C9 119.1(4) . . ?
C7 C8 C9 123.2(4) . . ?
C10 C9 C8 121.2(4) . . ?
C10 C9 HA 119.4 . . ?
C8 C9 HA 119.4 . . ?
C9 C10 C11 121.3(4) . . ?
C9 C10 HB 119.3 . . ?
C11 C10 HB 119.3 . . ?
C12 C11 C15 118.1(3) . . ?
C12 C11 C10 123.9(3) . . ?
C15 C11 C10 118.0(3) . . ?
C13 C12 C11 118.6(3) . . ?
C13 C12 HC 120.7 . . ?
C11 C12 HC 120.7 . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 HD 120.0 . . ?
C14 C13 HD 120.0 . . ?
N2 C14 C13 122.2(3) . . ?
N2 C14 HE 118.9 . . ?
C13 C14 HE 118.9 . . ?
N2 C15 C11 123.0(3) . . ?
N2 C15 C16 116.9(3) . . ?
C11 C15 C16 120.1(3) . . ?
N1 C16 C8 122.6(3) . . ?
N1 C16 C15 117.2(3) . . ?
C8 C16 C15 120.2(3) . . ?
C21 C20 C20 120.3(3) . 2 ?
C21 C20 HF 119.8 . . ?
C20 C20 HF 119.8 2 . ?
C20 C21 C20 119.4(6) 8_445 . ?
C20 C21 HG 120.3 8_445 . ?
C20 C21 HG 120.3 . . ?
C18 C17 C19 120.0(5) . 9_565 ?
C18 C17 HH 120.0 . . ?
C19 C17 HH 120.0 9_565 . ?
C17 C18 C19 120.7(5) . . ?
C17 C18 HI 119.7 . . ?
C19 C18 HI 119.7 . . ?
C17 C19 C18 119.4(5) 9_565 . ?
C17 C19 HJ 120.3 9_565 . ?
C18 C19 HJ 120.3 . . ?
F4 C3 F4 66.2(6) . 10_556 ?
F4 C3 F3 32.7(3) . 10_556 ?
F4 C3 F3 98.8(5) 10_556 10_556 ?
F4 C3 F3 98.8(5) . . ?
F4 C3 F3 32.7(3) 10_556 . ?
F3 C3 F3 131.0(6) 10_556 . ?
F4 C3 C4 116.1(4) . . ?
F4 C3 C4 116.1(4) 10_556 . ?
F3 C3 C4 99.9(3) 10_556 . ?
F3 C3 C4 99.9(3) . . ?
F4 C3 C2 115.0(4) . . ?
F4 C3 C2 115.0(4) 10_556 . ?
F3 C3 C2 104.6(3) 10_556 . ?
F3 C3 C2 104.6(3) . . ?
C4 C3 C2 118.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.080
_refine_diff_density_min         -0.990
_refine_diff_density_rms         0.148
