# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 986473'
_audit_update_record             
;
2014-02-12 deposited with the CCDC.
2017-04-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 N2 O2, 2(H2 O)'
_chemical_formula_sum            'C24 H20 N2 O4'
_chemical_formula_weight         400.42

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   13.077(3)
_cell_length_b                   10.396(2)
_cell_length_c                   15.667(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.261(2)
_cell_angle_gamma                90.00
_cell_volume                     2010.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2844
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      25.95

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9732
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11772
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         28.01
_reflns_number_total             2395
_reflns_number_gt                1735
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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. 

 The OH hydrogen atoms were located from the difference fourier map and refined
 isotropically subject to a distance restraint.  
;

_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)+(0.0515P)²+0.7163P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2395
_refine_ls_number_parameters     148
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1183
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.050
_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
O1 O 0.11436(10) 0.88499(11) 0.54319(8) 0.0633(3) Uani 1 1 d D . .
H1A H 0.0663(17) 0.888(2) 0.4798(11) 0.108(8) Uiso 1 1 d D . .
O2 O -0.01481(9) 0.93112(12) 0.37699(8) 0.0565(3) Uani 1 1 d D . .
H2C H -0.0593(14) 0.9933(16) 0.3852(13) 0.075(6) Uiso 1 1 d D . .
H2B H 0.0217(16) 0.9748(19) 0.3450(13) 0.092(7) Uiso 1 1 d D . .
N1 N 0.39415(9) 0.38893(11) 0.69320(7) 0.0405(3) Uani 1 1 d . . .
C1 C 0.29078(11) 0.38985(13) 0.63915(9) 0.0422(3) Uani 1 1 d . . .
C2 C 0.23370(12) 0.27457(15) 0.60862(11) 0.0525(4) Uani 1 1 d . . .
H2A H 0.1618 0.2772 0.5713 0.063 Uiso 1 1 calc R . .
C3 C 0.28375(12) 0.15993(15) 0.63374(11) 0.0541(4) Uani 1 1 d . . .
H3A H 0.2464 0.0839 0.6128 0.065 Uiso 1 1 calc R . .
C4 C 0.39207(12) 0.15553(13) 0.69148(10) 0.0476(4) Uani 1 1 d . . .
C5 C 0.44869(13) 0.03797(14) 0.72203(12) 0.0598(4) Uani 1 1 d . . .
H5A H 0.4137 -0.0399 0.7028 0.072 Uiso 1 1 calc R . .
C6 C 0.44399(10) 0.27443(12) 0.71997(9) 0.0402(3) Uani 1 1 d . . .
C7 C 0.24022(10) 0.51757(13) 0.61354(9) 0.0418(3) Uani 1 1 d . . .
C8 C 0.15486(11) 0.53745(15) 0.53308(10) 0.0511(4) Uani 1 1 d . . .
H8A H 0.1264 0.4679 0.4954 0.061 Uiso 1 1 calc R . .
C9 C 0.11200(12) 0.65863(15) 0.50861(10) 0.0532(4) Uani 1 1 d . . .
H9A H 0.0560 0.6703 0.4543 0.064 Uiso 1 1 calc R . .
C10 C 0.15199(11) 0.76256(14) 0.56444(10) 0.0471(4) Uani 1 1 d . . .
C11 C 0.23377(12) 0.74379(14) 0.64601(10) 0.0495(4) Uani 1 1 d . . .
H11A H 0.2589 0.8127 0.6852 0.059 Uiso 1 1 calc R . .
C12 C 0.27803(11) 0.62351(14) 0.66937(9) 0.0461(3) Uani 1 1 d . . .
H12A H 0.3344 0.6128 0.7236 0.055 Uiso 1 1 calc R . .


_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
O1 C10 1.3656(17) . ?
O1 H1A 0.986(16) . ?
O2 H2C 0.907(15) . ?
O2 H2B 0.919(15) . ?
N1 C1 1.3376(16) . ?
N1 C6 1.3555(16) . ?
C1 C2 1.4095(19) . ?
C1 C7 1.4786(19) . ?
C2 C3 1.354(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.408(2) . ?
C3 H3A 0.9300 . ?
C4 C6 1.4100(19) . ?
C4 C5 1.427(2) . ?
C5 C5 1.339(3) 2_656 ?
C5 H5A 0.9300 . ?
C6 C6 1.457(3) 2_656 ?
C7 C12 1.3918(19) . ?
C7 C8 1.3962(19) . ?
C8 C9 1.381(2) . ?
C8 H8A 0.9300 . ?
C9 C10 1.380(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.383(2) . ?
C11 C12 1.376(2) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 H1A 109.6(13) . . ?
H2C O2 H2B 101.4(17) . . ?
C1 N1 C6 118.98(11) . . ?
N1 C1 C2 121.35(13) . . ?
N1 C1 C7 116.50(12) . . ?
C2 C1 C7 122.15(12) . . ?
C3 C2 C1 119.91(14) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 120.18(13) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C3 C4 C6 116.89(13) . . ?
C3 C4 C5 122.96(13) . . ?
C6 C4 C5 120.14(14) . . ?
C5 C5 C4 121.10(9) 2_656 . ?
C5 C5 H5A 119.5 2_656 . ?
C4 C5 H5A 119.5 . . ?
N1 C6 C4 122.67(12) . . ?
N1 C6 C6 118.57(7) . 2_656 ?
C4 C6 C6 118.76(8) . 2_656 ?
C12 C7 C8 117.56(13) . . ?
C12 C7 C1 120.38(12) . . ?
C8 C7 C1 122.05(13) . . ?
C9 C8 C7 121.07(14) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C10 C9 C8 120.27(13) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
O1 C10 C9 122.98(13) . . ?
O1 C10 C11 117.61(13) . . ?
C9 C10 C11 119.41(13) . . ?
C12 C11 C10 120.22(14) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
C11 C12 C7 121.39(13) . . ?
C11 C12 H12A 119.3 . . ?
C7 C12 H12A 119.3 . . ?

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
C6 N1 C1 C2 -1.0(2) . . . . ?
C6 N1 C1 C7 178.96(12) . . . . ?
N1 C1 C2 C3 -0.3(2) . . . . ?
C7 C1 C2 C3 179.78(14) . . . . ?
C1 C2 C3 C4 1.1(2) . . . . ?
C2 C3 C4 C6 -0.6(2) . . . . ?
C2 C3 C4 C5 178.61(16) . . . . ?
C3 C4 C5 C5 -179.1(2) . . . 2_656 ?
C6 C4 C5 C5 0.1(3) . . . 2_656 ?
C1 N1 C6 C4 1.5(2) . . . . ?
C1 N1 C6 C6 -179.00(15) . . . 2_656 ?
C3 C4 C6 N1 -0.7(2) . . . . ?
C5 C4 C6 N1 -179.92(14) . . . . ?
C3 C4 C6 C6 179.78(16) . . . 2_656 ?
C5 C4 C6 C6 0.6(2) . . . 2_656 ?
N1 C1 C7 C12 -26.12(19) . . . . ?
C2 C1 C7 C12 153.83(14) . . . . ?
N1 C1 C7 C8 153.00(14) . . . . ?
C2 C1 C7 C8 -27.1(2) . . . . ?
C12 C7 C8 C9 2.0(2) . . . . ?
C1 C7 C8 C9 -177.12(14) . . . . ?
C7 C8 C9 C10 -1.1(2) . . . . ?
C8 C9 C10 O1 178.75(14) . . . . ?
C8 C9 C10 C11 -1.4(2) . . . . ?
O1 C10 C11 C12 -177.30(14) . . . . ?
C9 C10 C11 C12 2.8(2) . . . . ?
C10 C11 C12 C7 -1.9(2) . . . . ?
C8 C7 C12 C11 -0.6(2) . . . . ?
C1 C7 C12 C11 178.60(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O2 0.986(16) 1.670(16) 2.6385(16) 166(2) .
O2 H2C O1 0.907(15) 1.978(16) 2.8262(18) 155.1(17) 5_576
O2 H2B N1 0.919(15) 2.002(16) 2.8885(16) 161.6(19) 7_566

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.036




#==END
####################################################################### 
# 
# 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 986472'
_audit_update_record             
;
2014-02-12 deposited with the CCDC.
2017-04-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' 	C26 H20 N2 O2, 2(H2 O)'
_chemical_formula_sum            'C26 H24 N2 O4'
_chemical_formula_weight         428.47

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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/6'
'-y, x-y, z+1/3'
'-x, -y, z+1/2'
'-x+y, -x, z+2/3'
'y, -x+y, z+5/6'

_cell_length_a                   17.6523(18)
_cell_length_b                   17.6523(18)
_cell_length_c                   12.1223(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3271.3(8)
_cell_formula_units_Z            6
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3857
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      27.4

_exptl_crystal_description       Chip
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             1356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9765
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku SCX-Mini CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_reflns_number            34388
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_av_R_equivalents  0.1313
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.144
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5011
_reflns_number_gt                3022
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _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       'CrystalClear-SM Expert 2.0 (Rigaku, 2010)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 (Rigaku, 2010)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 (Rigaku, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 The reflection 0 1 0 was omitted from the refenement due to proximity to
 the beamstop.
 
 A number of electron denisty peaks, suggesting various disordered water
 molecules were apparent running along the c-axis.  The data were treated
 with the SQUEEZE routine in PLATON (Spek, 2009).  The electron density
 accounted for was 138 electrons per unit cell, or 23 electrons per molecule.
 This was taken to be equivalent to two waters per molecule.  The electron
 density thus accounted for has been included in the formula, formula weight,
 calculated density, mu and F(000).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0777P)²+1.3035P] 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_abs_structure_details 
; 
  The calculated value of the Flack parameter, and its ESD were found to be
 meaningless.  They have been removed.
;
_refine_ls_abs_structure_Flack   .
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5011
_refine_ls_number_parameters     271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1375
_refine_ls_R_factor_gt           0.0809
_refine_ls_wR_factor_ref         0.1941
_refine_ls_wR_factor_gt          0.1659
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2573(3) 0.2476(3) 0.7292(4) 0.0635(13) Uani 1 1 d . . . . .
O2 O 0.8132(3) 0.4460(3) 0.2598(3) 0.0513(11) Uani 1 1 d . . . . .
N1 N 0.2991(3) 0.3536(3) 0.2235(4) 0.0416(12) Uani 1 1 d . . . . .
N2 N 0.4503(3) 0.4092(3) 0.1024(4) 0.0394(12) Uani 1 1 d . . . . .
C1 C 0.2289(4) 0.3346(4) 0.2865(5) 0.0414(14) Uani 1 1 d . . . . .
C2 C 0.1584(4) 0.3424(4) 0.2455(6) 0.0491(16) Uani 1 1 d . . . . .
H2B H 0.1109 0.3315 0.2925 0.059 Uiso 1 1 calc R U . . .
C3 C 0.1585(4) 0.3657(4) 0.1382(6) 0.0547(18) Uani 1 1 d . . . . .
H3A H 0.1102 0.3692 0.1100 0.066 Uiso 1 1 calc R U . . .
C4 C 0.2303(4) 0.3846(4) 0.0689(5) 0.0448(14) Uani 1 1 d . . . . .
C5 C 0.2353(4) 0.4113(4) -0.0435(6) 0.0509(16) Uani 1 1 d . . . . .
H5A H 0.1870 0.4125 -0.0763 0.061 Uiso 1 1 calc R U . . .
C6 C 0.3086(4) 0.4348(4) -0.1036(6) 0.0535(16) Uani 1 1 d . . . . .
H6A H 0.3100 0.4512 -0.1786 0.064 Uiso 1 1 calc R U . . .
C7 C 0.3829(4) 0.4358(4) -0.0585(5) 0.0433(14) Uani 1 1 d . . . . .
C8 C 0.4618(5) 0.4649(4) -0.1173(5) 0.0521(17) Uani 1 1 d . . . . .
H8A H 0.4663 0.4836 -0.1918 0.063 Uiso 1 1 calc R U . . .
C9 C 0.5317(4) 0.4662(4) -0.0664(5) 0.0484(15) Uani 1 1 d . . . . .
H9A H 0.5851 0.4863 -0.1053 0.058 Uiso 1 1 calc R U . . .
C10 C 0.5242(4) 0.4373(4) 0.0449(4) 0.0364(13) Uani 1 1 d . . . . .
C11 C 0.3802(4) 0.4084(4) 0.0511(5) 0.0363(13) Uani 1 1 d . . . . .
C12 C 0.3011(4) 0.3806(4) 0.1172(5) 0.0395(13) Uani 1 1 d . . . . .
C13 C 0.2321(4) 0.3075(4) 0.4028(5) 0.0419(14) Uani 1 1 d . . . . .
C14 C 0.1618(4) 0.2774(4) 0.4738(6) 0.0524(17) Uani 1 1 d . . . . .
H14A H 0.1086 0.2720 0.4475 0.063 Uiso 1 1 calc R U . . .
C15 C 0.1661(4) 0.2549(4) 0.5823(5) 0.0504(16) Uani 1 1 d . . . . .
H15A H 0.1157 0.2317 0.6281 0.061 Uiso 1 1 calc R U . . .
C16 C 0.2441(4) 0.2663(4) 0.6232(5) 0.0484(15) Uani 1 1 d . . . . .
C17 C 0.3161(4) 0.2965(4) 0.5532(5) 0.0479(16) Uani 1 1 d . . . . .
H17A H 0.3696 0.3032 0.5807 0.058 Uiso 1 1 calc R U . . .
C18 C 0.3110(4) 0.3166(4) 0.4455(5) 0.0492(16) Uani 1 1 d . . . . .
H18A H 0.3607 0.3369 0.3989 0.059 Uiso 1 1 calc R U . . .
C19 C 0.1835(5) 0.2130(5) 0.8025(6) 0.075(2) Uani 1 1 d . . . . .
H19A H 0.2009 0.2029 0.8753 0.112 Uiso 1 1 calc R U . . .
H19B H 0.1365 0.1576 0.7730 0.112 Uiso 1 1 calc R U . . .
H19C H 0.1627 0.2549 0.8092 0.112 Uiso 1 1 calc R U . . .
C20 C 0.5994(4) 0.4378(3) 0.1028(5) 0.0366(13) Uani 1 1 d . . . . .
C21 C 0.6855(4) 0.4960(4) 0.0713(5) 0.0417(14) Uani 1 1 d . . . . .
H21A H 0.6961 0.5356 0.0124 0.050 Uiso 1 1 calc R U . . .
C22 C 0.7553(4) 0.4972(4) 0.1234(5) 0.0424(14) Uani 1 1 d . . . . .
H22A H 0.8134 0.5375 0.1009 0.051 Uiso 1 1 calc R U . . .
C23 C 0.7404(4) 0.4385(4) 0.2101(5) 0.0435(15) Uani 1 1 d . . . . .
C24 C 0.6551(4) 0.3794(4) 0.2426(5) 0.0464(16) Uani 1 1 d . . . . .
H24A H 0.6442 0.3394 0.3011 0.056 Uiso 1 1 calc R U . . .
C25 C 0.5847(4) 0.3799(4) 0.1871(5) 0.0430(14) Uani 1 1 d . . . . .
H25A H 0.5263 0.3394 0.2084 0.052 Uiso 1 1 calc R U . . .
C26 C 0.7989(5) 0.3916(5) 0.3549(6) 0.062(2) Uani 1 1 d . . . . .
H26A H 0.8553 0.4018 0.3832 0.092 Uiso 1 1 calc R U . . .
H26B H 0.7627 0.3300 0.3340 0.092 Uiso 1 1 calc R U . . .
H26C H 0.7689 0.4059 0.4123 0.092 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.375(7) . ?
O1 C19 1.437(9) . ?
O2 C23 1.363(7) . ?
O2 C26 1.440(8) . ?
N1 C1 1.348(7) . ?
N1 C12 1.368(8) . ?
N2 C10 1.338(7) . ?
N2 C11 1.378(7) . ?
C1 C2 1.409(8) . ?
C1 C13 1.498(8) . ?
C2 C3 1.364(9) . ?
C2 H2B 0.9500 . ?
C3 C4 1.413(9) . ?
C3 H3A 0.9500 . ?
C4 C12 1.414(8) . ?
C4 C5 1.430(9) . ?
C5 C6 1.356(9) . ?
C5 H5A 0.9500 . ?
C6 C7 1.414(8) . ?
C6 H6A 0.9500 . ?
C7 C11 1.407(8) . ?
C7 C8 1.413(9) . ?
C8 C9 1.370(9) . ?
C8 H8A 0.9500 . ?
C9 C10 1.425(8) . ?
C9 H9A 0.9500 . ?
C10 C20 1.497(8) . ?
C11 C12 1.465(8) . ?
C13 C14 1.381(8) . ?
C13 C18 1.417(8) . ?
C14 C15 1.387(10) . ?
C14 H14A 0.9500 . ?
C15 C16 1.380(9) . ?
C15 H15A 0.9500 . ?
C16 C17 1.394(9) . ?
C17 C18 1.368(8) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.375(8) . ?
C20 C21 1.397(8) . ?
C21 C22 1.376(8) . ?
C21 H21A 0.9500 . ?
C22 C23 1.405(8) . ?
C22 H22A 0.9500 . ?
C23 C24 1.393(8) . ?
C24 C25 1.417(8) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
C16 O1 C19 117.0(6) . . ?
C23 O2 C26 116.5(5) . . ?
C1 N1 C12 118.8(5) . . ?
C10 N2 C11 118.3(5) . . ?
N1 C1 C2 121.5(6) . . ?
N1 C1 C13 115.8(5) . . ?
C2 C1 C13 122.6(6) . . ?
C3 C2 C1 119.8(6) . . ?
C3 C2 H2B 120.1 . . ?
C1 C2 H2B 120.1 . . ?
C2 C3 C4 120.3(6) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 C12 116.9(6) . . ?
C3 C4 C5 123.0(6) . . ?
C12 C4 C5 120.0(6) . . ?
C6 C5 C4 120.4(6) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C7 122.2(6) . . ?
C5 C6 H6A 118.9 . . ?
C7 C6 H6A 118.9 . . ?
C11 C7 C8 117.4(5) . . ?
C11 C7 C6 119.3(6) . . ?
C8 C7 C6 123.3(6) . . ?
C9 C8 C7 119.6(6) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C8 C9 C10 120.0(6) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
N2 C10 C9 121.6(5) . . ?
N2 C10 C20 117.1(5) . . ?
C9 C10 C20 121.3(5) . . ?
N2 C11 C7 123.1(5) . . ?
N2 C11 C12 117.2(5) . . ?
C7 C11 C12 119.6(5) . . ?
N1 C12 C4 122.5(5) . . ?
N1 C12 C11 119.1(5) . . ?
C4 C12 C11 118.4(5) . . ?
C14 C13 C18 117.4(6) . . ?
C14 C13 C1 122.6(5) . . ?
C18 C13 C1 119.9(5) . . ?
C13 C14 C15 122.3(6) . . ?
C13 C14 H14A 118.9 . . ?
C15 C14 H14A 118.9 . . ?
C16 C15 C14 119.5(6) . . ?
C16 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?
O1 C16 C15 125.2(6) . . ?
O1 C16 C17 115.4(6) . . ?
C15 C16 C17 119.3(6) . . ?
C18 C17 C16 121.0(6) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C17 C18 C13 120.5(6) . . ?
C17 C18 H18A 119.8 . . ?
C13 C18 H18A 119.8 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 118.8(5) . . ?
C25 C20 C10 120.5(5) . . ?
C21 C20 C10 120.8(5) . . ?
C22 C21 C20 121.5(6) . . ?
C22 C21 H21A 119.2 . . ?
C20 C21 H21A 119.2 . . ?
C21 C22 C23 119.7(6) . . ?
C21 C22 H22A 120.1 . . ?
C23 C22 H22A 120.1 . . ?
O2 C23 C24 124.1(5) . . ?
O2 C23 C22 116.0(5) . . ?
C24 C23 C22 119.8(5) . . ?
C23 C24 C25 119.0(5) . . ?
C23 C24 H24A 120.5 . . ?
C25 C24 H24A 120.5 . . ?
C20 C25 C24 121.2(6) . . ?
C20 C25 H25A 119.4 . . ?
C24 C25 H25A 119.4 . . ?
O2 C26 H26A 109.5 . . ?
O2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 -0.4(8) . . . . ?
C12 N1 C1 C13 -178.7(5) . . . . ?
N1 C1 C2 C3 3.2(9) . . . . ?
C13 C1 C2 C3 -178.7(6) . . . . ?
C1 C2 C3 C4 -2.0(10) . . . . ?
C2 C3 C4 C12 -1.8(9) . . . . ?
C2 C3 C4 C5 -178.6(6) . . . . ?
C3 C4 C5 C6 175.0(6) . . . . ?
C12 C4 C5 C6 -1.6(9) . . . . ?
C4 C5 C6 C7 -1.2(10) . . . . ?
C5 C6 C7 C11 2.5(10) . . . . ?
C5 C6 C7 C8 -176.2(6) . . . . ?
C11 C7 C8 C9 -0.6(9) . . . . ?
C6 C7 C8 C9 178.1(6) . . . . ?
C7 C8 C9 C10 0.7(9) . . . . ?
C11 N2 C10 C9 0.3(8) . . . . ?
C11 N2 C10 C20 179.8(5) . . . . ?
C8 C9 C10 N2 -0.5(9) . . . . ?
C8 C9 C10 C20 180.0(6) . . . . ?
C10 N2 C11 C7 -0.2(8) . . . . ?
C10 N2 C11 C12 -177.7(5) . . . . ?
C8 C7 C11 N2 0.3(8) . . . . ?
C6 C7 C11 N2 -178.4(5) . . . . ?
C8 C7 C11 C12 177.8(5) . . . . ?
C6 C7 C11 C12 -0.9(8) . . . . ?
C1 N1 C12 C4 -3.6(8) . . . . ?
C1 N1 C12 C11 174.9(5) . . . . ?
C3 C4 C12 N1 4.7(9) . . . . ?
C5 C4 C12 N1 -178.5(5) . . . . ?
C3 C4 C12 C11 -173.8(5) . . . . ?
C5 C4 C12 C11 3.0(8) . . . . ?
N2 C11 C12 N1 -2.7(8) . . . . ?
C7 C11 C12 N1 179.7(5) . . . . ?
N2 C11 C12 C4 175.9(5) . . . . ?
C7 C11 C12 C4 -1.7(8) . . . . ?
N1 C1 C13 C14 -173.2(6) . . . . ?
C2 C1 C13 C14 8.6(9) . . . . ?
N1 C1 C13 C18 10.2(8) . . . . ?
C2 C1 C13 C18 -168.0(6) . . . . ?
C18 C13 C14 C15 -1.4(9) . . . . ?
C1 C13 C14 C15 -178.1(6) . . . . ?
C13 C14 C15 C16 3.0(10) . . . . ?
C19 O1 C16 C15 0.3(9) . . . . ?
C19 O1 C16 C17 -177.7(6) . . . . ?
C14 C15 C16 O1 179.2(6) . . . . ?
C14 C15 C16 C17 -2.9(10) . . . . ?
O1 C16 C17 C18 179.4(6) . . . . ?
C15 C16 C17 C18 1.3(10) . . . . ?
C16 C17 C18 C13 0.3(10) . . . . ?
C14 C13 C18 C17 -0.3(9) . . . . ?
C1 C13 C18 C17 176.5(6) . . . . ?
N2 C10 C20 C25 27.7(8) . . . . ?
C9 C10 C20 C25 -152.8(6) . . . . ?
N2 C10 C20 C21 -153.4(5) . . . . ?
C9 C10 C20 C21 26.1(8) . . . . ?
C25 C20 C21 C22 -0.9(8) . . . . ?
C10 C20 C21 C22 -179.8(5) . . . . ?
C20 C21 C22 C23 0.4(9) . . . . ?
C26 O2 C23 C24 -3.1(9) . . . . ?
C26 O2 C23 C22 174.7(5) . . . . ?
C21 C22 C23 O2 -177.8(5) . . . . ?
C21 C22 C23 C24 0.1(9) . . . . ?
O2 C23 C24 C25 177.7(6) . . . . ?
C22 C23 C24 C25 0.0(9) . . . . ?
C21 C20 C25 C24 1.0(9) . . . . ?
C10 C20 C25 C24 179.9(5) . . . . ?
C23 C24 C25 C20 -0.5(9) . . . . ?

_refine_diff_density_max         0.608
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-3


####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 986471'
_audit_update_record             
;
2014-02-12 deposited with the CCDC.
2017-04-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C56 H48 Cu N4 O4, F6 P, C2 H3 N'
_chemical_formula_sum            'C58 H51 Cu F6 N5 O4 P'
_chemical_formula_weight         1090.55

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'
P P 0.1023 0.0942 '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           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   8.3697(16)
_cell_length_b                   32.873(6)
_cell_length_c                   18.214(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.458(3)
_cell_angle_gamma                90.00
_cell_volume                     5002.2(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2155
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      21.53

_exptl_crystal_description       platelet
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2256
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9081
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30457
_diffrn_reflns_av_R_equivalents  0.1226
_diffrn_reflns_av_sigmaI/netI    0.1083
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.24
_diffrn_reflns_theta_max         27.91
_reflns_number_total             5955
_reflns_number_gt                3533
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXM'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0383P)²+0.0000P] 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         5955
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 0.0000 0.398436(15) 0.2500 0.01905(14) Uani 1 2 d S . .
P1 P 0.0000 0.65064(3) 0.2500 0.0319(3) Uani 1 2 d S . .
F1 F -0.1011(3) 0.68484(6) 0.20619(12) 0.0582(6) Uani 1 1 d . . .
F2 F -0.1017(3) 0.61659(6) 0.20647(10) 0.0555(6) Uani 1 1 d . . .
F3 F 0.1255(2) 0.65059(5) 0.18700(10) 0.0450(5) Uani 1 1 d . . .
O1 O -0.4338(2) 0.53415(6) 0.39885(10) 0.0246(5) Uani 1 1 d . . .
O2 O 0.3997(3) 0.27330(6) 0.46564(11) 0.0343(6) Uani 1 1 d . . .
N1 N -0.0694(3) 0.43222(7) 0.15909(12) 0.0180(5) Uani 1 1 d . . .
N2 N 0.1202(3) 0.36541(7) 0.17542(12) 0.0191(5) Uani 1 1 d . . .
N31 N 0.0925(9) 0.1982(3) 0.1106(4) 0.085(3) Uani 0.50 1 d P . .
C1 C -0.1539(3) 0.46696(8) 0.15274(15) 0.0179(6) Uani 1 1 d . . .
C2 C -0.1854(3) 0.48566(9) 0.08377(15) 0.0223(7) Uani 1 1 d . . .
H2A H -0.2444 0.5104 0.0805 0.027 Uiso 1 1 calc R . .
C3 C -0.1319(3) 0.46854(9) 0.02190(15) 0.0238(7) Uani 1 1 d . . .
H3A H -0.1567 0.4807 -0.0247 0.029 Uiso 1 1 calc R . .
C4 C -0.0400(3) 0.43286(9) 0.02685(15) 0.0221(7) Uani 1 1 d . . .
C5 C 0.0192(4) 0.41316(10) -0.03585(16) 0.0286(8) Uani 1 1 d . . .
H5A H -0.0035 0.4244 -0.0834 0.034 Uiso 1 1 calc R . .
C6 C 0.1067(4) 0.37887(10) -0.02837(16) 0.0280(8) Uani 1 1 d . . .
H6A H 0.1442 0.3661 -0.0708 0.034 Uiso 1 1 calc R . .
C7 C 0.1439(3) 0.36144(9) 0.04232(16) 0.0240(7) Uani 1 1 d . . .
C8 C 0.2387(4) 0.32634(9) 0.05331(17) 0.0285(8) Uani 1 1 d . . .
H8A H 0.2808 0.3130 0.0125 0.034 Uiso 1 1 calc R . .
C9 C 0.2697(4) 0.31176(9) 0.12186(17) 0.0280(7) Uani 1 1 d . . .
H9A H 0.3327 0.2879 0.1289 0.034 Uiso 1 1 calc R . .
C10 C 0.2093(3) 0.33158(9) 0.18380(15) 0.0216(7) Uani 1 1 d . . .
C11 C 0.0870(3) 0.37989(8) 0.10558(15) 0.0207(7) Uani 1 1 d . . .
C12 C -0.0106(3) 0.41589(9) 0.09717(14) 0.0186(6) Uani 1 1 d . . .
C13 C -0.2187(3) 0.48490(8) 0.21896(14) 0.0165(6) Uani 1 1 d . . .
C14 C -0.2235(3) 0.52687(9) 0.22761(15) 0.0202(6) Uani 1 1 d . . .
H14A H -0.1792 0.5439 0.1919 0.024 Uiso 1 1 calc R . .
C15 C -0.2917(3) 0.54429(9) 0.28731(15) 0.0226(7) Uani 1 1 d . . .
H15A H -0.2929 0.5730 0.2927 0.027 Uiso 1 1 calc R . .
C16 C -0.3584(3) 0.51972(9) 0.33946(15) 0.0202(6) Uani 1 1 d . . .
C17 C -0.3484(3) 0.47710(9) 0.33416(14) 0.0190(6) Uani 1 1 d . . .
C18 C -0.2814(3) 0.46079(8) 0.27358(14) 0.0184(6) Uani 1 1 d . . .
H18A H -0.2776 0.4320 0.2687 0.022 Uiso 1 1 calc R . .
C19 C -0.4605(4) 0.57702(9) 0.40195(17) 0.0340(8) Uani 1 1 d . . .
H19A H -0.5227 0.5834 0.4444 0.051 Uiso 1 1 calc R . .
H19B H -0.5198 0.5859 0.3567 0.051 Uiso 1 1 calc R . .
H19C H -0.3574 0.5912 0.4069 0.051 Uiso 1 1 calc R . .
C20 C -0.4115(3) 0.45008(9) 0.39293(15) 0.0254(7) Uani 1 1 d . . .
H20A H -0.4107 0.4217 0.3764 0.038 Uiso 1 1 calc R . .
H20B H -0.5213 0.4581 0.4021 0.038 Uiso 1 1 calc R . .
H20C H -0.3436 0.4529 0.4384 0.038 Uiso 1 1 calc R . .
C21 C 0.2503(3) 0.31575(9) 0.25772(16) 0.0239(7) Uani 1 1 d . . .
C22 C 0.2760(4) 0.27432(9) 0.26888(17) 0.0277(7) Uani 1 1 d . . .
H22A H 0.2613 0.2562 0.2284 0.033 Uiso 1 1 calc R . .
C23 C 0.3223(4) 0.25903(9) 0.33728(18) 0.0300(8) Uani 1 1 d . . .
H23A H 0.3385 0.2306 0.3437 0.036 Uiso 1 1 calc R . .
C24 C 0.3451(4) 0.28500(9) 0.39635(17) 0.0273(7) Uani 1 1 d . . .
C25 C 0.3190(3) 0.32716(9) 0.38851(16) 0.0230(7) Uani 1 1 d . . .
C26 C 0.2734(3) 0.34139(9) 0.31906(16) 0.0229(7) Uani 1 1 d . . .
H26A H 0.2569 0.3698 0.3125 0.027 Uiso 1 1 calc R . .
C27 C 0.4486(4) 0.23169(10) 0.47481(19) 0.0459(10) Uani 1 1 d . . .
H27A H 0.4838 0.2269 0.5264 0.069 Uiso 1 1 calc R . .
H27B H 0.5371 0.2260 0.4434 0.069 Uiso 1 1 calc R . .
H27C H 0.3583 0.2137 0.4609 0.069 Uiso 1 1 calc R . .
C28 C 0.3435(4) 0.35510(9) 0.45280(16) 0.0283(7) Uani 1 1 d . . .
H28A H 0.3382 0.3834 0.4357 0.042 Uiso 1 1 calc R . .
H28B H 0.4486 0.3499 0.4777 0.042 Uiso 1 1 calc R . .
H28C H 0.2598 0.3504 0.4872 0.042 Uiso 1 1 calc R . .
C31 C 0.0562(9) 0.1890(3) 0.1673(5) 0.052(2) Uani 0.50 1 d P . .
C32 C 0.0000 0.17843(18) 0.2500 0.0705(19) Uani 1 2 d S . .
H32A H 0.0730 0.1583 0.2732 0.106 Uiso 0.50 1 calc PR . .
H32B H -0.1090 0.1674 0.2464 0.106 Uiso 0.50 1 calc PR . .
H32C H 0.0024 0.2033 0.2798 0.106 Uiso 0.50 1 calc PR . .


_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 2.049(2) . ?
Cu1 N1 2.049(2) 2 ?
Cu1 N2 2.050(2) . ?
Cu1 N2 2.050(2) 2 ?
P1 F2 1.589(2) 2 ?
P1 F2 1.589(2) . ?
P1 F1 1.592(2) 2 ?
P1 F1 1.592(2) . ?
P1 F3 1.6018(18) . ?
P1 F3 1.6018(18) 2 ?
O1 C16 1.370(3) . ?
O1 C19 1.429(3) . ?
O2 C24 1.371(3) . ?
O2 C27 1.435(3) . ?
N1 C1 1.345(3) . ?
N1 C12 1.367(3) . ?
N2 C10 1.343(3) . ?
N2 C11 1.371(3) . ?
N31 C31 1.134(10) . ?
C1 C2 1.409(4) . ?
C1 C13 1.475(4) . ?
C2 C3 1.360(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.402(4) . ?
C3 H3A 0.9500 . ?
C4 C12 1.405(4) . ?
C4 C5 1.427(4) . ?
C5 C6 1.346(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.427(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.408(4) . ?
C7 C11 1.410(4) . ?
C8 C9 1.348(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.422(4) . ?
C9 H9A 0.9500 . ?
C10 C21 1.465(4) . ?
C11 C12 1.441(4) . ?
C13 C14 1.389(4) . ?
C13 C18 1.399(4) . ?
C14 C15 1.382(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.389(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.407(4) . ?
C17 C18 1.376(4) . ?
C17 C20 1.511(4) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.392(4) . ?
C21 C26 1.404(4) . ?
C22 C23 1.377(4) . ?
C22 H22A 0.9500 . ?
C23 C24 1.378(4) . ?
C23 H23A 0.9500 . ?
C24 C25 1.409(4) . ?
C25 C26 1.381(4) . ?
C25 C28 1.493(4) . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C31 C32 1.643(9) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?

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 114.35(12) . 2 ?
N1 Cu1 N2 83.00(9) . . ?
N1 Cu1 N2 134.13(9) 2 . ?
N1 Cu1 N2 134.13(9) . 2 ?
N1 Cu1 N2 83.00(9) 2 2 ?
N2 Cu1 N2 116.02(13) . 2 ?
F2 P1 F2 90.43(17) 2 . ?
F2 P1 F1 89.69(12) 2 2 ?
F2 P1 F1 179.71(13) . 2 ?
F2 P1 F1 179.71(13) 2 . ?
F2 P1 F1 89.69(12) . . ?
F1 P1 F1 90.18(18) 2 . ?
F2 P1 F3 90.12(10) 2 . ?
F2 P1 F3 89.81(10) . . ?
F1 P1 F3 90.45(10) 2 . ?
F1 P1 F3 89.62(10) . . ?
F2 P1 F3 89.80(10) 2 2 ?
F2 P1 F3 90.11(10) . 2 ?
F1 P1 F3 89.63(10) 2 2 ?
F1 P1 F3 90.46(10) . 2 ?
F3 P1 F3 179.89(15) . 2 ?
C16 O1 C19 117.0(2) . . ?
C24 O2 C27 116.8(3) . . ?
C1 N1 C12 118.4(2) . . ?
C1 N1 Cu1 130.69(18) . . ?
C12 N1 Cu1 110.81(18) . . ?
C10 N2 C11 118.3(2) . . ?
C10 N2 Cu1 130.92(19) . . ?
C11 N2 Cu1 110.53(18) . . ?
N1 C1 C2 121.1(3) . . ?
N1 C1 C13 119.1(2) . . ?
C2 C1 C13 119.8(2) . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 C12 117.1(3) . . ?
C3 C4 C5 122.9(3) . . ?
C12 C4 C5 119.9(3) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6A 119.5 . . ?
C7 C6 H6A 119.5 . . ?
C8 C7 C11 116.9(3) . . ?
C8 C7 C6 123.2(3) . . ?
C11 C7 C6 119.9(3) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9A 119.5 . . ?
C10 C9 H9A 119.5 . . ?
N2 C10 C9 120.7(3) . . ?
N2 C10 C21 119.8(3) . . ?
C9 C10 C21 119.5(3) . . ?
N2 C11 C7 123.3(3) . . ?
N2 C11 C12 117.8(2) . . ?
C7 C11 C12 118.9(3) . . ?
N1 C12 C4 123.0(3) . . ?
N1 C12 C11 117.7(2) . . ?
C4 C12 C11 119.3(3) . . ?
C14 C13 C18 117.9(3) . . ?
C14 C13 C1 120.3(2) . . ?
C18 C13 C1 121.8(2) . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14A 119.4 . . ?
C13 C14 H14A 119.4 . . ?
C14 C15 C16 119.9(3) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
O1 C16 C15 124.2(3) . . ?
O1 C16 C17 115.6(2) . . ?
C15 C16 C17 120.2(3) . . ?
C18 C17 C16 118.2(2) . . ?
C18 C17 C20 121.0(3) . . ?
C16 C17 C20 120.8(2) . . ?
C17 C18 C13 122.5(3) . . ?
C17 C18 H18A 118.7 . . ?
C13 C18 H18A 118.7 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 117.3(3) . . ?
C22 C21 C10 120.5(3) . . ?
C26 C21 C10 122.1(3) . . ?
C23 C22 C21 121.4(3) . . ?
C23 C22 H22A 119.3 . . ?
C21 C22 H22A 119.3 . . ?
C22 C23 C24 119.9(3) . . ?
C22 C23 H23A 120.0 . . ?
C24 C23 H23A 120.0 . . ?
O2 C24 C23 124.6(3) . . ?
O2 C24 C25 114.2(3) . . ?
C23 C24 C25 121.1(3) . . ?
C26 C25 C24 117.3(3) . . ?
C26 C25 C28 121.8(3) . . ?
C24 C25 C28 120.8(3) . . ?
C25 C26 C21 122.9(3) . . ?
C25 C26 H26A 118.6 . . ?
C21 C26 H26A 118.6 . . ?
O2 C27 H27A 109.5 . . ?
O2 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O2 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N31 C31 C32 176.6(9) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 N1 C1 -38.9(2) 2 . . . ?
N2 Cu1 N1 C1 -174.5(2) . . . . ?
N2 Cu1 N1 C1 65.7(3) 2 . . . ?
N1 Cu1 N1 C12 138.2(2) 2 . . . ?
N2 Cu1 N1 C12 2.57(18) . . . . ?
N2 Cu1 N1 C12 -117.20(19) 2 . . . ?
N1 Cu1 N2 C10 -177.4(2) . . . . ?
N1 Cu1 N2 C10 65.2(3) 2 . . . ?
N2 Cu1 N2 C10 -41.3(2) 2 . . . ?
N1 Cu1 N2 C11 -3.94(18) . . . . ?
N1 Cu1 N2 C11 -121.30(18) 2 . . . ?
N2 Cu1 N2 C11 132.17(19) 2 . . . ?
C12 N1 C1 C2 1.7(4) . . . . ?
Cu1 N1 C1 C2 178.62(19) . . . . ?
C12 N1 C1 C13 179.8(2) . . . . ?
Cu1 N1 C1 C13 -3.4(4) . . . . ?
N1 C1 C2 C3 0.7(4) . . . . ?
C13 C1 C2 C3 -177.3(2) . . . . ?
C1 C2 C3 C4 -2.2(4) . . . . ?
C2 C3 C4 C12 1.4(4) . . . . ?
C2 C3 C4 C5 179.6(3) . . . . ?
C3 C4 C5 C6 -179.9(3) . . . . ?
C12 C4 C5 C6 -1.7(4) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C5 C6 C7 C8 -178.1(3) . . . . ?
C5 C6 C7 C11 0.8(4) . . . . ?
C11 C7 C8 C9 0.6(4) . . . . ?
C6 C7 C8 C9 179.6(3) . . . . ?
C7 C8 C9 C10 -0.7(4) . . . . ?
C11 N2 C10 C9 1.0(4) . . . . ?
Cu1 N2 C10 C9 174.1(2) . . . . ?
C11 N2 C10 C21 178.6(2) . . . . ?
Cu1 N2 C10 C21 -8.3(4) . . . . ?
C8 C9 C10 N2 -0.1(4) . . . . ?
C8 C9 C10 C21 -177.7(3) . . . . ?
C10 N2 C11 C7 -1.1(4) . . . . ?
Cu1 N2 C11 C7 -175.5(2) . . . . ?
C10 N2 C11 C12 179.1(2) . . . . ?
Cu1 N2 C11 C12 4.7(3) . . . . ?
C8 C7 C11 N2 0.3(4) . . . . ?
C6 C7 C11 N2 -178.7(3) . . . . ?
C8 C7 C11 C12 -180.0(3) . . . . ?
C6 C7 C11 C12 1.0(4) . . . . ?
C1 N1 C12 C4 -2.7(4) . . . . ?
Cu1 N1 C12 C4 179.9(2) . . . . ?
C1 N1 C12 C11 176.7(2) . . . . ?
Cu1 N1 C12 C11 -0.8(3) . . . . ?
C3 C4 C12 N1 1.1(4) . . . . ?
C5 C4 C12 N1 -177.2(3) . . . . ?
C3 C4 C12 C11 -178.2(2) . . . . ?
C5 C4 C12 C11 3.5(4) . . . . ?
N2 C11 C12 N1 -2.7(4) . . . . ?
C7 C11 C12 N1 177.5(2) . . . . ?
N2 C11 C12 C4 176.6(2) . . . . ?
C7 C11 C12 C4 -3.2(4) . . . . ?
N1 C1 C13 C14 143.5(3) . . . . ?
C2 C1 C13 C14 -38.4(4) . . . . ?
N1 C1 C13 C18 -38.5(4) . . . . ?
C2 C1 C13 C18 139.6(3) . . . . ?
C18 C13 C14 C15 -1.6(4) . . . . ?
C1 C13 C14 C15 176.5(2) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C19 O1 C16 C15 7.4(4) . . . . ?
C19 O1 C16 C17 -173.8(2) . . . . ?
C14 C15 C16 O1 -177.4(2) . . . . ?
C14 C15 C16 C17 3.8(4) . . . . ?
O1 C16 C17 C18 176.6(2) . . . . ?
C15 C16 C17 C18 -4.5(4) . . . . ?
O1 C16 C17 C20 -2.5(4) . . . . ?
C15 C16 C17 C20 176.3(2) . . . . ?
C16 C17 C18 C13 2.2(4) . . . . ?
C20 C17 C18 C13 -178.6(2) . . . . ?
C14 C13 C18 C17 0.8(4) . . . . ?
C1 C13 C18 C17 -177.2(2) . . . . ?
N2 C10 C21 C22 151.1(3) . . . . ?
C9 C10 C21 C22 -31.2(4) . . . . ?
N2 C10 C21 C26 -32.2(4) . . . . ?
C9 C10 C21 C26 145.4(3) . . . . ?
C26 C21 C22 C23 0.0(4) . . . . ?
C10 C21 C22 C23 176.8(3) . . . . ?
C21 C22 C23 C24 -0.4(5) . . . . ?
C27 O2 C24 C23 5.5(4) . . . . ?
C27 O2 C24 C25 -172.0(3) . . . . ?
C22 C23 C24 O2 -176.1(3) . . . . ?
C22 C23 C24 C25 1.2(5) . . . . ?
O2 C24 C25 C26 176.1(2) . . . . ?
C23 C24 C25 C26 -1.5(4) . . . . ?
O2 C24 C25 C28 -2.6(4) . . . . ?
C23 C24 C25 C28 179.8(3) . . . . ?
C24 C25 C26 C21 1.0(4) . . . . ?
C28 C25 C26 C21 179.7(3) . . . . ?
C22 C21 C26 C25 -0.3(4) . . . . ?
C10 C21 C26 C25 -177.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.077
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 986470'
_audit_update_record             
;
2014-02-12 deposited with the CCDC.
2017-04-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C52 H40 Cu N4 O4, F6 P'
_chemical_formula_sum            'C52 H40 Cu F6 N4 O4 P'
_chemical_formula_weight         993.39

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.724(4)
_cell_length_b                   14.159(4)
_cell_length_c                   14.164(4)
_cell_angle_alpha                63.174(4)
_cell_angle_beta                 61.260(3)
_cell_angle_gamma                73.411(4)
_cell_volume                     2145.4(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5084
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      24.78

_exptl_crystal_description       chip
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_F_000             1020
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.627
_shelx_estimated_absorpt_T_min   0.895
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6260
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25825
_diffrn_reflns_av_unetI/netI     0.0848
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.618
_diffrn_reflns_theta_max         27.941
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             10029
_reflns_number_gt                7241
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000

_reflns_special_details          
; 
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXM'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 The structure was found to be affcted by non-merohedral twinning, with a 
 twin law of [0.045 -0.955 -0.056 -1.045 -0.045 0.056 0 0 -1], and a refined
 twin fraction of 0.34.  This was accounted for in the refinement by the use
 of an HKLF5 file, generated using the TWINROTMAT routine in PLATON
 (Spek, 2009).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.1159P)²+2.8643P] 
 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     SHELXL
_refine_ls_extinction_coef       0.0083(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10029
_refine_ls_number_parameters     619
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0713
_refine_ls_wR_factor_ref         0.2248
_refine_ls_wR_factor_gt          0.2050
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.06193(4) 0.44501(4) 0.24826(5) 0.01527(17) Uani 1 1 d . . . . .
P1 P 0.40143(11) 0.08547(10) 0.73717(11) 0.0247(3) Uani 1 1 d . . . . .
F1 F 0.3481(4) 0.0971(4) 0.8583(3) 0.0685(13) Uani 1 1 d . . . . .
F2 F 0.5191(3) 0.1062(4) 0.7134(4) 0.0664(13) Uani 1 1 d . . . . .
F3 F 0.4536(3) 0.0761(3) 0.6143(3) 0.0511(10) Uani 1 1 d . . . . .
F4 F 0.2826(3) 0.0616(3) 0.7623(4) 0.0488(10) Uani 1 1 d . . . . .
F5 F 0.4286(3) -0.0385(3) 0.7949(3) 0.0505(10) Uani 1 1 d . . . . .
F6 F 0.3718(3) 0.2093(3) 0.6767(3) 0.0525(10) Uani 1 1 d . . . . .
O1 O 0.1672(3) 0.8874(3) 0.1583(3) 0.0299(8) Uani 1 1 d . . . . .
O2 O 0.4811(3) 0.2350(3) -0.0654(3) 0.0262(8) Uani 1 1 d . . . . .
O3 O 0.2105(3) 0.0245(3) 0.5897(3) 0.0258(8) Uani 1 1 d . . . . .
O4 O -0.4252(3) 0.4299(3) 0.3419(3) 0.0282(8) Uani 1 1 d . . . . .
N1 N -0.0801(3) 0.4735(3) 0.3808(3) 0.0167(8) Uani 1 1 d . . . . .
N2 N 0.0047(3) 0.3001(3) 0.3233(3) 0.0154(7) Uani 1 1 d . . . . .
N3 N 0.2204(3) 0.4780(3) 0.1881(3) 0.0158(7) Uani 1 1 d . . . . .
N4 N 0.0605(3) 0.5780(3) 0.1068(3) 0.0145(7) Uani 1 1 d . . . . .
C1 C -0.1243(4) 0.5645(4) 0.3966(4) 0.0182(9) Uani 1 1 d . . . . .
C2 C -0.2367(4) 0.5780(4) 0.4719(4) 0.0218(10) Uani 1 1 d . . . . .
H2A H -0.2679 0.6452 0.4781 0.026 Uiso 1 1 calc R U . . .
C3 C -0.3004(4) 0.4938(4) 0.5358(4) 0.0253(10) Uani 1 1 d . . . . .
H3A H -0.3754 0.5017 0.5887 0.030 Uiso 1 1 calc R U . . .
C4 C -0.2551(4) 0.3959(4) 0.5234(4) 0.0214(10) Uani 1 1 d . . . . .
C5 C -0.3134(4) 0.3012(4) 0.5887(4) 0.0274(11) Uani 1 1 d . . . . .
H5A H -0.3880 0.3034 0.6449 0.033 Uiso 1 1 calc R U . . .
C6 C -0.2651(4) 0.2103(4) 0.5723(4) 0.0256(11) Uani 1 1 d . . . . .
H6A H -0.3037 0.1480 0.6208 0.031 Uiso 1 1 calc R U . . .
C7 C -0.1560(4) 0.2053(4) 0.4826(4) 0.0225(10) Uani 1 1 d . . . . .
C8 C -0.1044(4) 0.1143(4) 0.4551(4) 0.0254(11) Uani 1 1 d . . . . .
H8A H -0.1410 0.0507 0.4988 0.030 Uiso 1 1 calc R U . . .
C9 C -0.0023(4) 0.1176(4) 0.3660(4) 0.0238(10) Uani 1 1 d . . . . .
H9A H 0.0325 0.0559 0.3479 0.029 Uiso 1 1 calc R U . . .
C10 C 0.0529(4) 0.2117(4) 0.2999(4) 0.0179(9) Uani 1 1 d . . . . .
C11 C -0.0962(4) 0.2960(3) 0.4149(4) 0.0166(9) Uani 1 1 d . . . . .
C12 C -0.1446(4) 0.3906(4) 0.4407(4) 0.0176(9) Uani 1 1 d . . . . .
C13 C -0.0502(4) 0.6514(4) 0.3323(4) 0.0170(9) Uani 1 1 d . . . . .
C14 C -0.0830(4) 0.7543(4) 0.2704(4) 0.0209(10) Uani 1 1 d . . . . .
H14A H -0.1549 0.7694 0.2701 0.025 Uiso 1 1 calc R U . . .
C15 C -0.0127(4) 0.8344(4) 0.2096(4) 0.0231(10) Uani 1 1 d . . . . .
H15A H -0.0354 0.9035 0.1659 0.028 Uiso 1 1 calc R U . . .
C16 C 0.0924(4) 0.8136(4) 0.2125(4) 0.0217(10) Uani 1 1 d . . . . .
C17 C 0.1249(4) 0.7116(4) 0.2759(4) 0.0220(10) Uani 1 1 d . . . . .
H17A H 0.1957 0.6970 0.2786 0.026 Uiso 1 1 calc R U . . .
C18 C 0.0550(4) 0.6317(4) 0.3347(4) 0.0185(9) Uani 1 1 d . . . . .
H18A H 0.0782 0.5624 0.3774 0.022 Uiso 1 1 calc R U . . .
C19 C 0.1383(5) 0.9926(4) 0.0928(5) 0.0364(13) Uani 1 1 d . . . . .
H19A H 0.2008 1.0358 0.0555 0.055 Uiso 1 1 calc R U . . .
H19B H 0.0725 1.0230 0.1444 0.055 Uiso 1 1 calc R U . . .
H19C H 0.1215 0.9920 0.0332 0.055 Uiso 1 1 calc R U . . .
C20 C 0.1648(4) 0.2151(4) 0.2041(4) 0.0179(9) Uani 1 1 d . . . . .
C21 C 0.2418(4) 0.1267(4) 0.2102(4) 0.0214(10) Uani 1 1 d . . . . .
H21A H 0.2209 0.0630 0.2765 0.026 Uiso 1 1 calc R U . . .
C22 C 0.3489(4) 0.1283(4) 0.1222(4) 0.0235(10) Uani 1 1 d . . . . .
H22A H 0.3998 0.0665 0.1279 0.028 Uiso 1 1 calc R U . . .
C23 C 0.3797(4) 0.2222(4) 0.0258(4) 0.0209(10) Uani 1 1 d . . . . .
C24 C 0.3039(4) 0.3125(4) 0.0185(4) 0.0197(9) Uani 1 1 d . . . . .
H24A H 0.3254 0.3768 -0.0467 0.024 Uiso 1 1 calc R U . . .
C25 C 0.1982(4) 0.3084(4) 0.1057(4) 0.0189(9) Uani 1 1 d . . . . .
H25A H 0.1470 0.3700 0.0992 0.023 Uiso 1 1 calc R U . . .
C26 C 0.5546(4) 0.1413(4) -0.0726(5) 0.0305(11) Uani 1 1 d . . . . .
H26A H 0.6244 0.1608 -0.1420 0.046 Uiso 1 1 calc R U . . .
H26B H 0.5192 0.0933 -0.0771 0.046 Uiso 1 1 calc R U . . .
H26C H 0.5707 0.1055 -0.0034 0.046 Uiso 1 1 calc R U . . .
C27 C 0.3002(4) 0.4250(4) 0.2262(4) 0.0179(9) Uani 1 1 d . . . . .
C28 C 0.4014(4) 0.4690(4) 0.1776(4) 0.0201(9) Uani 1 1 d . . . . .
H28A H 0.4569 0.4302 0.2061 0.024 Uiso 1 1 calc R U . . .
C29 C 0.4210(4) 0.5659(4) 0.0907(4) 0.0250(10) Uani 1 1 d . . . . .
H29A H 0.4890 0.5954 0.0597 0.030 Uiso 1 1 calc R U . . .
C30 C 0.3397(4) 0.6225(4) 0.0466(4) 0.0199(9) Uani 1 1 d . . . . .
C31 C 0.3514(4) 0.7263(4) -0.0424(4) 0.0215(10) Uani 1 1 d . . . . .
H31A H 0.4181 0.7590 -0.0763 0.026 Uiso 1 1 calc R U . . .
C32 C 0.2697(4) 0.7786(4) -0.0793(4) 0.0217(10) Uani 1 1 d . . . . .
H32A H 0.2788 0.8480 -0.1378 0.026 Uiso 1 1 calc R U . . .
C33 C 0.1695(4) 0.7299(4) -0.0307(4) 0.0183(9) Uani 1 1 d . . . . .
C34 C 0.0791(4) 0.7819(4) -0.0622(4) 0.0216(10) Uani 1 1 d . . . . .
H34A H 0.0853 0.8510 -0.1211 0.026 Uiso 1 1 calc R U . . .
C35 C -0.0176(4) 0.7335(4) -0.0083(4) 0.0216(10) Uani 1 1 d . . . . .
H35A H -0.0787 0.7691 -0.0288 0.026 Uiso 1 1 calc R U . . .
C36 C -0.0251(4) 0.6299(3) 0.0780(4) 0.0170(9) Uani 1 1 d . . . . .
C37 C 0.1546(4) 0.6284(3) 0.0562(4) 0.0156(8) Uani 1 1 d . . . . .
C38 C 0.2409(4) 0.5740(3) 0.0975(4) 0.0151(8) Uani 1 1 d . . . . .
C39 C 0.2783(4) 0.3199(4) 0.3212(4) 0.0166(9) Uani 1 1 d . . . . .
C40 C 0.3647(4) 0.2377(4) 0.3230(4) 0.0202(9) Uani 1 1 d . . . . .
H40A H 0.4375 0.2504 0.2627 0.024 Uiso 1 1 calc R U . . .
C41 C 0.3453(4) 0.1383(4) 0.4116(4) 0.0234(10) Uani 1 1 d . . . . .
H41A H 0.4047 0.0838 0.4124 0.028 Uiso 1 1 calc R U . . .
C42 C 0.2393(4) 0.1188(4) 0.4989(4) 0.0196(9) Uani 1 1 d . . . . .
C43 C 0.1534(4) 0.1993(4) 0.4977(4) 0.0189(9) Uani 1 1 d . . . . .
H43A H 0.0803 0.1859 0.5571 0.023 Uiso 1 1 calc R U . . .
C44 C 0.1728(4) 0.2980(4) 0.4115(4) 0.0156(9) Uani 1 1 d . . . . .
H44A H 0.1134 0.3527 0.4133 0.019 Uiso 1 1 calc R U . . .
C45 C 0.2971(5) -0.0598(4) 0.5951(5) 0.0311(12) Uani 1 1 d . . . . .
H45A H 0.2655 -0.1243 0.6609 0.047 Uiso 1 1 calc R U . . .
H45B H 0.3533 -0.0399 0.6051 0.047 Uiso 1 1 calc R U . . .
H45C H 0.3320 -0.0731 0.5229 0.047 Uiso 1 1 calc R U . . .
C46 C -0.1281(4) 0.5758(3) 0.1419(4) 0.0167(9) Uani 1 1 d . . . . .
C47 C -0.2295(4) 0.6280(4) 0.1923(4) 0.0194(9) Uani 1 1 d . . . . .
H47A H -0.2322 0.7005 0.1793 0.023 Uiso 1 1 calc R U . . .
C48 C -0.3263(4) 0.5773(4) 0.2608(4) 0.0227(10) Uani 1 1 d . . . . .
H48A H -0.3940 0.6135 0.2978 0.027 Uiso 1 1 calc R U . . .
C49 C -0.3246(4) 0.4728(4) 0.2755(4) 0.0190(9) Uani 1 1 d . . . . .
C50 C -0.2251(4) 0.4197(4) 0.2225(4) 0.0202(9) Uani 1 1 d . . . . .
H50A H -0.2236 0.3488 0.2313 0.024 Uiso 1 1 calc R U . . .
C51 C -0.1273(4) 0.4713(3) 0.1564(4) 0.0172(9) Uani 1 1 d . . . . .
H51A H -0.0591 0.4348 0.1206 0.021 Uiso 1 1 calc R U . . .
C52 C -0.4237(4) 0.3182(4) 0.3741(5) 0.0293(11) Uani 1 1 d . . . . .
H52A H -0.4995 0.2962 0.4249 0.044 Uiso 1 1 calc R U . . .
H52B H -0.3752 0.2794 0.4153 0.044 Uiso 1 1 calc R U . . .
H52C H -0.3952 0.3024 0.3042 0.044 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 2.026(4) . ?
Cu1 N3 2.028(4) . ?
Cu1 N4 2.042(4) . ?
Cu1 N1 2.050(4) . ?
P1 F2 1.571(4) . ?
P1 F1 1.577(4) . ?
P1 F3 1.586(4) . ?
P1 F5 1.586(3) . ?
P1 F6 1.595(4) . ?
P1 F4 1.596(4) . ?
O1 C16 1.366(6) . ?
O1 C19 1.417(6) . ?
O2 C23 1.357(6) . ?
O2 C26 1.431(6) . ?
O3 C42 1.362(5) . ?
O3 C45 1.428(6) . ?
O4 C49 1.369(5) . ?
O4 C52 1.432(6) . ?
N1 C1 1.328(6) . ?
N1 C12 1.361(6) . ?
N2 C10 1.343(6) . ?
N2 C11 1.362(6) . ?
N3 C27 1.337(6) . ?
N3 C38 1.367(6) . ?
N4 C36 1.336(6) . ?
N4 C37 1.365(5) . ?
C1 C2 1.410(6) . ?
C1 C13 1.479(6) . ?
C2 C3 1.366(7) . ?
C2 H2A 0.9500 . ?
C3 C4 1.401(7) . ?
C3 H3A 0.9500 . ?
C4 C12 1.409(6) . ?
C4 C5 1.441(7) . ?
C5 C6 1.336(8) . ?
C5 H5A 0.9500 . ?
C6 C7 1.432(7) . ?
C6 H6A 0.9500 . ?
C7 C11 1.405(6) . ?
C7 C8 1.407(7) . ?
C8 C9 1.358(7) . ?
C8 H8A 0.9500 . ?
C9 C10 1.411(6) . ?
C9 H9A 0.9500 . ?
C10 C20 1.477(6) . ?
C11 C12 1.439(7) . ?
C13 C14 1.395(6) . ?
C13 C18 1.404(6) . ?
C14 C15 1.379(7) . ?
C14 H14A 0.9500 . ?
C15 C16 1.404(7) . ?
C15 H15A 0.9500 . ?
C16 C17 1.392(7) . ?
C17 C18 1.375(6) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.387(6) . ?
C20 C25 1.403(6) . ?
C21 C22 1.395(7) . ?
C21 H21A 0.9500 . ?
C22 C23 1.392(7) . ?
C22 H22A 0.9500 . ?
C23 C24 1.397(7) . ?
C24 C25 1.376(7) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.407(6) . ?
C27 C39 1.475(6) . ?
C28 C29 1.356(7) . ?
C28 H28A 0.9500 . ?
C29 C30 1.408(7) . ?
C29 H29A 0.9500 . ?
C30 C38 1.405(6) . ?
C30 C31 1.429(6) . ?
C31 C32 1.348(7) . ?
C31 H31A 0.9500 . ?
C32 C33 1.429(6) . ?
C32 H32A 0.9500 . ?
C33 C37 1.397(6) . ?
C33 C34 1.412(7) . ?
C34 C35 1.375(7) . ?
C34 H34A 0.9500 . ?
C35 C36 1.416(6) . ?
C35 H35A 0.9500 . ?
C36 C46 1.471(6) . ?
C37 C38 1.442(6) . ?
C39 C44 1.395(6) . ?
C39 C40 1.405(6) . ?
C40 C41 1.388(7) . ?
C40 H40A 0.9500 . ?
C41 C42 1.384(7) . ?
C41 H41A 0.9500 . ?
C42 C43 1.388(7) . ?
C43 C44 1.369(6) . ?
C43 H43A 0.9500 . ?
C44 H44A 0.9500 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 C47 1.388(6) . ?
C46 C51 1.397(6) . ?
C47 C48 1.378(7) . ?
C47 H47A 0.9500 . ?
C48 C49 1.392(7) . ?
C48 H48A 0.9500 . ?
C49 C50 1.390(7) . ?
C50 C51 1.395(6) . ?
C50 H50A 0.9500 . ?
C51 H51A 0.9500 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?

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 127.54(15) . . ?
N2 Cu1 N4 134.19(15) . . ?
N3 Cu1 N4 83.37(15) . . ?
N2 Cu1 N1 83.08(15) . . ?
N3 Cu1 N1 129.77(15) . . ?
N4 Cu1 N1 102.73(15) . . ?
F2 P1 F1 91.0(3) . . ?
F2 P1 F3 89.5(2) . . ?
F1 P1 F3 178.8(3) . . ?
F2 P1 F5 90.4(2) . . ?
F1 P1 F5 91.2(3) . . ?
F3 P1 F5 89.9(2) . . ?
F2 P1 F6 91.4(2) . . ?
F1 P1 F6 90.2(2) . . ?
F3 P1 F6 88.6(2) . . ?
F5 P1 F6 177.7(2) . . ?
F2 P1 F4 178.7(2) . . ?
F1 P1 F4 89.2(2) . . ?
F3 P1 F4 90.4(2) . . ?
F5 P1 F4 88.35(19) . . ?
F6 P1 F4 89.9(2) . . ?
C16 O1 C19 118.2(4) . . ?
C23 O2 C26 117.3(4) . . ?
C42 O3 C45 117.1(4) . . ?
C49 O4 C52 117.1(4) . . ?
C1 N1 C12 119.0(4) . . ?
C1 N1 Cu1 128.9(3) . . ?
C12 N1 Cu1 110.2(3) . . ?
C10 N2 C11 118.7(4) . . ?
C10 N2 Cu1 130.3(3) . . ?
C11 N2 Cu1 110.9(3) . . ?
C27 N3 C38 118.6(4) . . ?
C27 N3 Cu1 130.7(3) . . ?
C38 N3 Cu1 110.5(3) . . ?
C36 N4 C37 119.1(4) . . ?
C36 N4 Cu1 128.9(3) . . ?
C37 N4 Cu1 110.0(3) . . ?
N1 C1 C2 121.6(4) . . ?
N1 C1 C13 117.2(4) . . ?
C2 C1 C13 121.2(4) . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 C12 117.1(4) . . ?
C3 C4 C5 124.8(4) . . ?
C12 C4 C5 118.1(5) . . ?
C6 C5 C4 121.6(5) . . ?
C6 C5 H5A 119.2 . . ?
C4 C5 H5A 119.2 . . ?
C5 C6 C7 121.1(4) . . ?
C5 C6 H6A 119.4 . . ?
C7 C6 H6A 119.4 . . ?
C11 C7 C8 116.7(4) . . ?
C11 C7 C6 119.5(5) . . ?
C8 C7 C6 123.7(4) . . ?
C9 C8 C7 119.9(4) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C8 C9 C10 120.7(5) . . ?
C8 C9 H9A 119.6 . . ?
C10 C9 H9A 119.6 . . ?
N2 C10 C9 120.6(4) . . ?
N2 C10 C20 118.6(4) . . ?
C9 C10 C20 120.8(4) . . ?
N2 C11 C7 123.3(4) . . ?
N2 C11 C12 117.8(4) . . ?
C7 C11 C12 118.9(4) . . ?
N1 C12 C4 122.4(4) . . ?
N1 C12 C11 117.3(4) . . ?
C4 C12 C11 120.3(4) . . ?
C14 C13 C18 118.4(4) . . ?
C14 C13 C1 121.6(4) . . ?
C18 C13 C1 120.0(4) . . ?
C15 C14 C13 121.1(4) . . ?
C15 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C14 C15 C16 119.9(4) . . ?
C14 C15 H15A 120.1 . . ?
C16 C15 H15A 120.1 . . ?
O1 C16 C17 115.8(4) . . ?
O1 C16 C15 124.8(4) . . ?
C17 C16 C15 119.4(4) . . ?
C18 C17 C16 120.3(4) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C17 C18 C13 120.9(4) . . ?
C17 C18 H18A 119.6 . . ?
C13 C18 H18A 119.6 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 117.7(4) . . ?
C21 C20 C10 121.0(4) . . ?
C25 C20 C10 121.3(4) . . ?
C20 C21 C22 122.2(4) . . ?
C20 C21 H21A 118.9 . . ?
C22 C21 H21A 118.9 . . ?
C23 C22 C21 118.8(4) . . ?
C23 C22 H22A 120.6 . . ?
C21 C22 H22A 120.6 . . ?
O2 C23 C22 124.9(4) . . ?
O2 C23 C24 115.1(4) . . ?
C22 C23 C24 120.0(4) . . ?
C25 C24 C23 120.1(4) . . ?
C25 C24 H24A 119.9 . . ?
C23 C24 H24A 119.9 . . ?
C24 C25 C20 121.2(4) . . ?
C24 C25 H25A 119.4 . . ?
C20 C25 H25A 119.4 . . ?
O2 C26 H26A 109.5 . . ?
O2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N3 C27 C28 120.8(4) . . ?
N3 C27 C39 118.0(4) . . ?
C28 C27 C39 121.2(4) . . ?
C29 C28 C27 121.0(4) . . ?
C29 C28 H28A 119.5 . . ?
C27 C28 H28A 119.5 . . ?
C28 C29 C30 119.5(4) . . ?
C28 C29 H29A 120.2 . . ?
C30 C29 H29A 120.2 . . ?
C38 C30 C29 116.9(4) . . ?
C38 C30 C31 119.5(4) . . ?
C29 C30 C31 123.6(4) . . ?
C32 C31 C30 121.4(4) . . ?
C32 C31 H31A 119.3 . . ?
C30 C31 H31A 119.3 . . ?
C31 C32 C33 120.1(4) . . ?
C31 C32 H32A 119.9 . . ?
C33 C32 H32A 119.9 . . ?
C37 C33 C34 116.5(4) . . ?
C37 C33 C32 120.5(4) . . ?
C34 C33 C32 122.9(4) . . ?
C35 C34 C33 120.6(4) . . ?
C35 C34 H34A 119.7 . . ?
C33 C34 H34A 119.7 . . ?
C34 C35 C36 119.2(4) . . ?
C34 C35 H35A 120.4 . . ?
C36 C35 H35A 120.4 . . ?
N4 C36 C35 121.2(4) . . ?
N4 C36 C46 117.1(4) . . ?
C35 C36 C46 121.6(4) . . ?
N4 C37 C33 123.4(4) . . ?
N4 C37 C38 117.5(4) . . ?
C33 C37 C38 119.1(4) . . ?
N3 C38 C30 123.1(4) . . ?
N3 C38 C37 117.6(4) . . ?
C30 C38 C37 119.3(4) . . ?
C44 C39 C40 117.7(4) . . ?
C44 C39 C27 122.0(4) . . ?
C40 C39 C27 120.3(4) . . ?
C41 C40 C39 120.9(4) . . ?
C41 C40 H40A 119.5 . . ?
C39 C40 H40A 119.5 . . ?
C42 C41 C40 119.9(4) . . ?
C42 C41 H41A 120.1 . . ?
C40 C41 H41A 120.1 . . ?
O3 C42 C41 125.0(4) . . ?
O3 C42 C43 115.5(4) . . ?
C41 C42 C43 119.5(4) . . ?
C44 C43 C42 120.6(4) . . ?
C44 C43 H43A 119.7 . . ?
C42 C43 H43A 119.7 . . ?
C43 C44 C39 121.3(4) . . ?
C43 C44 H44A 119.4 . . ?
C39 C44 H44A 119.4 . . ?
O3 C45 H45A 109.5 . . ?
O3 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
O3 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C47 C46 C51 118.1(4) . . ?
C47 C46 C36 119.8(4) . . ?
C51 C46 C36 122.0(4) . . ?
C48 C47 C46 121.6(4) . . ?
C48 C47 H47A 119.2 . . ?
C46 C47 H47A 119.2 . . ?
C47 C48 C49 119.8(4) . . ?
C47 C48 H48A 120.1 . . ?
C49 C48 H48A 120.1 . . ?
O4 C49 C50 124.3(4) . . ?
O4 C49 C48 115.8(4) . . ?
C50 C49 C48 119.9(4) . . ?
C49 C50 C51 119.5(4) . . ?
C49 C50 H50A 120.2 . . ?
C51 C50 H50A 120.2 . . ?
C50 C51 C46 121.0(4) . . ?
C50 C51 H51A 119.5 . . ?
C46 C51 H51A 119.5 . . ?
O4 C52 H52A 109.5 . . ?
O4 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
O4 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 -1.4(6) . . . . ?
Cu1 N1 C1 C2 161.4(3) . . . . ?
C12 N1 C1 C13 178.2(4) . . . . ?
Cu1 N1 C1 C13 -19.0(6) . . . . ?
N1 C1 C2 C3 4.1(7) . . . . ?
C13 C1 C2 C3 -175.5(4) . . . . ?
C1 C2 C3 C4 -2.2(7) . . . . ?
C2 C3 C4 C12 -2.1(7) . . . . ?
C2 C3 C4 C5 178.0(4) . . . . ?
C3 C4 C5 C6 179.9(5) . . . . ?
C12 C4 C5 C6 0.0(7) . . . . ?
C4 C5 C6 C7 -4.8(8) . . . . ?
C5 C6 C7 C11 3.5(7) . . . . ?
C5 C6 C7 C8 -174.8(5) . . . . ?
C11 C7 C8 C9 -0.6(7) . . . . ?
C6 C7 C8 C9 177.7(5) . . . . ?
C7 C8 C9 C10 -0.3(7) . . . . ?
C11 N2 C10 C9 2.6(6) . . . . ?
Cu1 N2 C10 C9 178.6(3) . . . . ?
C11 N2 C10 C20 -177.1(4) . . . . ?
Cu1 N2 C10 C20 -1.0(6) . . . . ?
C8 C9 C10 N2 -0.6(7) . . . . ?
C8 C9 C10 C20 179.0(4) . . . . ?
C10 N2 C11 C7 -3.7(6) . . . . ?
Cu1 N2 C11 C7 179.5(3) . . . . ?
C10 N2 C11 C12 178.1(4) . . . . ?
Cu1 N2 C11 C12 1.3(5) . . . . ?
C8 C7 C11 N2 2.7(7) . . . . ?
C6 C7 C11 N2 -175.7(4) . . . . ?
C8 C7 C11 C12 -179.1(4) . . . . ?
C6 C7 C11 C12 2.5(6) . . . . ?
C1 N1 C12 C4 -3.2(6) . . . . ?
Cu1 N1 C12 C4 -169.0(3) . . . . ?
C1 N1 C12 C11 175.6(4) . . . . ?
Cu1 N1 C12 C11 9.8(5) . . . . ?
C3 C4 C12 N1 4.9(7) . . . . ?
C5 C4 C12 N1 -175.2(4) . . . . ?
C3 C4 C12 C11 -173.9(4) . . . . ?
C5 C4 C12 C11 6.0(6) . . . . ?
N2 C11 C12 N1 -7.8(6) . . . . ?
C7 C11 C12 N1 173.9(4) . . . . ?
N2 C11 C12 C4 171.1(4) . . . . ?
C7 C11 C12 C4 -7.2(6) . . . . ?
N1 C1 C13 C14 131.9(5) . . . . ?
C2 C1 C13 C14 -48.5(6) . . . . ?
N1 C1 C13 C18 -49.4(6) . . . . ?
C2 C1 C13 C18 130.2(5) . . . . ?
C18 C13 C14 C15 2.1(7) . . . . ?
C1 C13 C14 C15 -179.2(4) . . . . ?
C13 C14 C15 C16 -2.0(7) . . . . ?
C19 O1 C16 C17 -179.8(5) . . . . ?
C19 O1 C16 C15 -1.0(7) . . . . ?
C14 C15 C16 O1 -178.1(4) . . . . ?
C14 C15 C16 C17 0.7(7) . . . . ?
O1 C16 C17 C18 179.3(4) . . . . ?
C15 C16 C17 C18 0.4(7) . . . . ?
C16 C17 C18 C13 -0.2(7) . . . . ?
C14 C13 C18 C17 -1.0(7) . . . . ?
C1 C13 C18 C17 -179.7(4) . . . . ?
N2 C10 C20 C21 145.8(4) . . . . ?
C9 C10 C20 C21 -33.9(6) . . . . ?
N2 C10 C20 C25 -32.0(6) . . . . ?
C9 C10 C20 C25 148.3(4) . . . . ?
C25 C20 C21 C22 -0.6(7) . . . . ?
C10 C20 C21 C22 -178.5(4) . . . . ?
C20 C21 C22 C23 0.8(7) . . . . ?
C26 O2 C23 C22 11.2(7) . . . . ?
C26 O2 C23 C24 -169.2(4) . . . . ?
C21 C22 C23 O2 179.6(4) . . . . ?
C21 C22 C23 C24 0.0(7) . . . . ?
O2 C23 C24 C25 179.5(4) . . . . ?
C22 C23 C24 C25 -1.0(7) . . . . ?
C23 C24 C25 C20 1.1(7) . . . . ?
C21 C20 C25 C24 -0.3(7) . . . . ?
C10 C20 C25 C24 177.6(4) . . . . ?
C38 N3 C27 C28 2.7(6) . . . . ?
Cu1 N3 C27 C28 -173.2(3) . . . . ?
C38 N3 C27 C39 -177.9(4) . . . . ?
Cu1 N3 C27 C39 6.2(6) . . . . ?
N3 C27 C28 C29 -0.3(7) . . . . ?
C39 C27 C28 C29 -179.7(4) . . . . ?
C27 C28 C29 C30 -1.3(7) . . . . ?
C28 C29 C30 C38 0.4(7) . . . . ?
C28 C29 C30 C31 178.1(5) . . . . ?
C38 C30 C31 C32 -0.4(7) . . . . ?
C29 C30 C31 C32 -178.0(5) . . . . ?
C30 C31 C32 C33 -1.0(7) . . . . ?
C31 C32 C33 C37 0.7(7) . . . . ?
C31 C32 C33 C34 177.5(5) . . . . ?
C37 C33 C34 C35 0.3(7) . . . . ?
C32 C33 C34 C35 -176.6(5) . . . . ?
C33 C34 C35 C36 -1.0(7) . . . . ?
C37 N4 C36 C35 3.5(6) . . . . ?
Cu1 N4 C36 C35 165.5(3) . . . . ?
C37 N4 C36 C46 -175.0(4) . . . . ?
Cu1 N4 C36 C46 -13.0(6) . . . . ?
C34 C35 C36 N4 -0.9(7) . . . . ?
C34 C35 C36 C46 177.5(4) . . . . ?
C36 N4 C37 C33 -4.4(6) . . . . ?
Cu1 N4 C37 C33 -169.6(3) . . . . ?
C36 N4 C37 C38 174.1(4) . . . . ?
Cu1 N4 C37 C38 8.9(5) . . . . ?
C34 C33 C37 N4 2.5(6) . . . . ?
C32 C33 C37 N4 179.4(4) . . . . ?
C34 C33 C37 C38 -176.0(4) . . . . ?
C32 C33 C37 C38 0.9(6) . . . . ?
C27 N3 C38 C30 -3.6(6) . . . . ?
Cu1 N3 C38 C30 173.0(3) . . . . ?
C27 N3 C38 C37 178.6(4) . . . . ?
Cu1 N3 C38 C37 -4.8(5) . . . . ?
C29 C30 C38 N3 2.1(7) . . . . ?
C31 C30 C38 N3 -175.7(4) . . . . ?
C29 C30 C38 C37 179.8(4) . . . . ?
C31 C30 C38 C37 2.0(6) . . . . ?
N4 C37 C38 N3 -3.0(6) . . . . ?
C33 C37 C38 N3 175.6(4) . . . . ?
N4 C37 C38 C30 179.2(4) . . . . ?
C33 C37 C38 C30 -2.3(6) . . . . ?
N3 C27 C39 C44 -36.4(6) . . . . ?
C28 C27 C39 C44 143.0(4) . . . . ?
N3 C27 C39 C40 143.5(4) . . . . ?
C28 C27 C39 C40 -37.1(6) . . . . ?
C44 C39 C40 C41 0.1(7) . . . . ?
C27 C39 C40 C41 -179.8(4) . . . . ?
C39 C40 C41 C42 0.9(7) . . . . ?
C45 O3 C42 C41 0.7(7) . . . . ?
C45 O3 C42 C43 -178.9(4) . . . . ?
C40 C41 C42 O3 179.7(4) . . . . ?
C40 C41 C42 C43 -0.7(7) . . . . ?
O3 C42 C43 C44 179.0(4) . . . . ?
C41 C42 C43 C44 -0.6(7) . . . . ?
C42 C43 C44 C39 1.7(7) . . . . ?
C40 C39 C44 C43 -1.5(6) . . . . ?
C27 C39 C44 C43 178.5(4) . . . . ?
N4 C36 C46 C47 128.8(5) . . . . ?
C35 C36 C46 C47 -49.7(6) . . . . ?
N4 C36 C46 C51 -49.6(6) . . . . ?
C35 C36 C46 C51 131.9(5) . . . . ?
C51 C46 C47 C48 3.8(7) . . . . ?
C36 C46 C47 C48 -174.6(4) . . . . ?
C46 C47 C48 C49 -3.4(7) . . . . ?
C52 O4 C49 C50 10.9(7) . . . . ?
C52 O4 C49 C48 -170.3(4) . . . . ?
C47 C48 C49 O4 -178.0(4) . . . . ?
C47 C48 C49 C50 0.9(7) . . . . ?
O4 C49 C50 C51 179.8(4) . . . . ?
C48 C49 C50 C51 1.0(7) . . . . ?
C49 C50 C51 C46 -0.5(7) . . . . ?
C47 C46 C51 C50 -1.9(7) . . . . ?
C36 C46 C51 C50 176.5(4) . . . . ?

_refine_diff_density_max         1.548
_refine_diff_density_min         -0.817
_refine_diff_density_rms         0.136
