# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1439669'
_audit_update_record             
;
2015-11-30 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 N3 O3'
_chemical_formula_weight         295.29

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           Tetragonal
_symmetry_space_group_name_H-M   'P4(3)   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   8.76240(10)
_cell_length_b                   8.76240(10)
_cell_length_c                   18.3758(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1410.89(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8771
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      23.62

_exptl_crystal_description       needle
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9662
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_process_details   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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33826
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3510
_reflns_number_gt                2811
_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. 
;

_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)+(0.0570P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(11)
_refine_ls_number_reflns         3510
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.47518(14) 0.24954(13) 0.23421(7) 0.0229(3) Uani 1 1 d . . .
O2 O 0.58979(18) 0.13875(19) 0.36044(9) 0.0427(4) Uani 1 1 d . . .
O3 O 0.66276(18) -0.08654(16) 0.32670(9) 0.0406(4) Uani 1 1 d . . .
N1 N 1.16382(16) 0.00696(17) 0.18259(8) 0.0189(3) Uani 1 1 d . . .
H1 H 1.1479 -0.0208 0.2268 0.023 Uiso 1 1 calc R . .
N2 N 1.12142(16) 0.11217(16) 0.07342(9) 0.0189(3) Uani 1 1 d . . .
N3 N 0.64740(17) 0.05117(18) 0.31671(9) 0.0241(4) Uani 1 1 d . . .
C1 C 1.2947(2) -0.01804(19) 0.14243(10) 0.0180(4) Uani 1 1 d . . .
C2 C 1.26756(19) 0.0477(2) 0.07432(10) 0.0184(4) Uani 1 1 d . . .
C3 C 1.3769(2) 0.0382(2) 0.01919(11) 0.0230(4) Uani 1 1 d . . .
H3A H 1.3600 0.0806 -0.0265 0.028 Uiso 1 1 calc R . .
C4 C 1.5112(2) -0.0366(2) 0.03539(11) 0.0257(4) Uani 1 1 d . . .
H4 H 1.5857 -0.0455 -0.0004 0.031 Uiso 1 1 calc R . .
C5 C 1.5384(2) -0.0996(2) 0.10437(11) 0.0246(4) Uani 1 1 d . . .
H5 H 1.6310 -0.1478 0.1134 0.030 Uiso 1 1 calc R . .
C6 C 1.4311(2) -0.0918(2) 0.15888(10) 0.0217(4) Uani 1 1 d . . .
H6 H 1.4488 -0.1338 0.2046 0.026 Uiso 1 1 calc R . .
C7 C 1.0647(2) 0.08402(19) 0.13882(10) 0.0179(4) Uani 1 1 d . . .
C8 C 0.9112(2) 0.1277(2) 0.16248(9) 0.0184(4) Uani 1 1 d . . .
C9 C 0.8249(2) 0.2327(2) 0.12303(10) 0.0200(4) Uani 1 1 d . . .
H9 H 0.8654 0.2735 0.0805 0.024 Uiso 1 1 calc R . .
C10 C 0.6808(2) 0.2781(2) 0.14524(11) 0.0208(4) Uani 1 1 d . . .
H10 H 0.6263 0.3486 0.1177 0.025 Uiso 1 1 calc R . .
C11 C 0.6172(2) 0.2185(2) 0.20869(11) 0.0196(4) Uani 1 1 d . . .
C12 C 0.7053(2) 0.11482(19) 0.24834(10) 0.0201(4) Uani 1 1 d . . .
C13 C 0.8471(2) 0.0674(2) 0.22576(10) 0.0192(4) Uani 1 1 d . . .
H13 H 0.9004 -0.0049 0.2527 0.023 Uiso 1 1 calc R . .
C14 C 0.3832(2) 0.3588(2) 0.19531(11) 0.0230(4) Uani 1 1 d . . .
H14A H 0.2773 0.3467 0.2096 0.028 Uiso 1 1 calc R . .
H14B H 0.3904 0.3384 0.1435 0.028 Uiso 1 1 calc R . .
C15 C 0.4321(2) 0.5194(2) 0.20978(11) 0.0237(4) Uani 1 1 d . . .
H15 H 0.3835 0.5965 0.1839 0.028 Uiso 1 1 calc R . .
C16 C 0.5391(2) 0.5602(2) 0.25649(12) 0.0291(5) Uani 1 1 d . . .
H16A H 0.5904 0.4864 0.2834 0.035 Uiso 1 1 calc R . .
H16B H 0.5632 0.6628 0.2625 0.035 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 C11 1.358(2) . ?
O1 C14 1.441(2) . ?
O2 N3 1.220(2) . ?
O3 N3 1.228(2) . ?
N1 C7 1.363(2) . ?
N1 C1 1.381(2) . ?
N2 C7 1.324(2) . ?
N2 C2 1.400(2) . ?
N3 C12 1.465(2) . ?
C1 C6 1.392(2) . ?
C1 C2 1.398(3) . ?
C2 C3 1.397(3) . ?
C3 C4 1.379(3) . ?
C4 C5 1.403(3) . ?
C5 C6 1.375(3) . ?
C7 C8 1.464(3) . ?
C8 C9 1.394(3) . ?
C8 C13 1.395(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.394(3) . ?
C11 C12 1.397(3) . ?
C12 C13 1.375(2) . ?
C14 C15 1.495(3) . ?
C15 C16 1.321(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C14 118.32(14) . . ?
C7 N1 C1 107.01(15) . . ?
C7 N2 C2 104.95(15) . . ?
O2 N3 O3 124.39(17) . . ?
O2 N3 C12 117.93(15) . . ?
O3 N3 C12 117.67(15) . . ?
N1 C1 C6 132.10(17) . . ?
N1 C1 C2 105.79(15) . . ?
C6 C1 C2 122.11(17) . . ?
C3 C2 C1 120.53(16) . . ?
C3 C2 N2 130.03(17) . . ?
C1 C2 N2 109.40(16) . . ?
C4 C3 C2 117.19(18) . . ?
C3 C4 C5 121.81(18) . . ?
C6 C5 C4 121.48(17) . . ?
C5 C6 C1 116.86(17) . . ?
N2 C7 N1 112.85(15) . . ?
N2 C7 C8 124.48(16) . . ?
N1 C7 C8 122.66(16) . . ?
C9 C8 C13 117.71(16) . . ?
C9 C8 C7 121.07(16) . . ?
C13 C8 C7 121.22(16) . . ?
C10 C9 C8 122.06(17) . . ?
C9 C10 C11 120.20(16) . . ?
O1 C11 C10 125.47(16) . . ?
O1 C11 C12 117.15(16) . . ?
C10 C11 C12 117.35(16) . . ?
C13 C12 C11 122.57(16) . . ?
C13 C12 N3 117.17(16) . . ?
C11 C12 N3 120.26(15) . . ?
C12 C13 C8 120.07(17) . . ?
O1 C14 C15 112.14(15) . . ?
C16 C15 C14 125.06(18) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.046


_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1439670'
_audit_update_record             
;
2015-11-30 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H26 Ag N7 O9'
_chemical_formula_weight         760.47

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'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2/c  '

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

_cell_length_a                   26.7698(3)
_cell_length_b                   7.36720(10)
_cell_length_c                   15.5539(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.7580(10)
_cell_angle_gamma                90.00
_cell_volume                     3039.44(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5816
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      23.76

_exptl_crystal_description       prism
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1544
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6912
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46487
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_av_sigmaI/netI    0.0629
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         26.38
_reflns_number_total             6232
_reflns_number_gt                4468
_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. 
;

_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)+(0.0263P)²+2.5107P] 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         6232
_refine_ls_number_parameters     457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0778
_refine_ls_wR_factor_gt          0.0682
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
Ag1 Ag 1.0000 0.35010(5) 0.7500 0.01859(10) Uani 1 2 d S . .
Ag2 Ag 0.5000 0.20061(5) 0.2500 0.02074(11) Uani 1 2 d S . .
O1 O 0.82351(8) -0.0529(3) 0.46664(13) 0.0216(5) Uani 1 1 d . . .
O2 O 0.87129(9) 0.0689(3) 0.71048(14) 0.0307(6) Uani 1 1 d . . .
O3 O 0.84022(9) -0.1601(3) 0.63426(15) 0.0291(6) Uani 1 1 d . . .
O4 O 0.71242(8) 0.5175(3) 0.49631(14) 0.0257(6) Uani 1 1 d . . .
O5 O 0.63642(11) 0.5410(5) 0.27039(18) 0.0682(11) Uani 1 1 d . . .
O6 O 0.70563(10) 0.4107(4) 0.32758(17) 0.0448(8) Uani 1 1 d . . .
O7 O 0.50603(10) 0.6077(4) 0.18358(15) 0.0376(7) Uani 1 1 d . . .
O8 O 0.5314(2) 0.8323(7) 0.2683(4) 0.0453(15) Uani 0.50 1 d P A -1
O9 O 0.97208(8) 0.3148(3) 0.19226(14) 0.0249(6) Uani 1 1 d . B .
O10 O 0.9869(3) 0.0679(6) 0.2587(7) 0.039(2) Uani 0.50 1 d P B -1
N1 N 1.03309(10) 0.3293(3) 0.63315(16) 0.0169(6) Uani 1 1 d . . .
N2 N 1.04489(9) 0.3199(3) 0.49453(16) 0.0172(6) Uani 1 1 d . . .
H2N H 1.0391 0.2993 0.4397 0.021 Uiso 1 1 calc R . .
N3 N 0.86530(10) -0.0206(4) 0.64313(17) 0.0214(7) Uani 1 1 d . . .
N4 N 0.48545(10) 0.2018(4) 0.37963(16) 0.0199(6) Uani 1 1 d . . .
N5 N 0.48568(10) 0.2380(4) 0.52116(17) 0.0222(7) Uani 1 1 d . . .
H5N H 0.4963 0.2631 0.5745 0.027 Uiso 1 1 calc R . .
N6 N 0.66204(12) 0.4628(5) 0.3297(2) 0.0382(9) Uani 1 1 d . . .
N7 N 0.5101(3) 0.6885(7) 0.2544(13) 0.022(2) Uani 0.50 1 d P . -1
N8 N 1.0000 0.2287(6) 0.2500 0.0230(10) Uani 1 2 d S . .
C1 C 1.07966(12) 0.4069(4) 0.6246(2) 0.0178(7) Uani 1 1 d . . .
C2 C 1.08770(12) 0.4023(4) 0.5376(2) 0.0178(7) Uani 1 1 d . . .
C3 C 1.13077(12) 0.4718(4) 0.5098(2) 0.0205(8) Uani 1 1 d . . .
H3 H 1.1356 0.4693 0.4517 0.025 Uiso 1 1 calc R . .
C4 C 1.16599(12) 0.5449(4) 0.5729(2) 0.0232(8) Uani 1 1 d . . .
H4 H 1.1957 0.5914 0.5571 0.028 Uiso 1 1 calc R . .
C5 C 1.15849(12) 0.5517(4) 0.6601(2) 0.0234(8) Uani 1 1 d . . .
H5 H 1.1832 0.6034 0.7005 0.028 Uiso 1 1 calc R . .
C6 C 1.11538(12) 0.4837(4) 0.6875(2) 0.0210(8) Uani 1 1 d . . .
H6 H 1.1104 0.4888 0.7454 0.025 Uiso 1 1 calc R . .
C7 C 1.01363(11) 0.2769(4) 0.5535(2) 0.0158(7) Uani 1 1 d . . .
C8 C 0.96509(11) 0.1860(4) 0.5304(2) 0.0157(7) Uani 1 1 d . . .
C9 C 0.94581(12) 0.1519(4) 0.4439(2) 0.0191(7) Uani 1 1 d . . .
H9 H 0.9647 0.1848 0.4005 0.023 Uiso 1 1 calc R . .
C10 C 0.89963(12) 0.0710(4) 0.4214(2) 0.0190(7) Uani 1 1 d . . .
H10A H 0.8877 0.0531 0.3631 0.023 Uiso 1 1 calc R . .
C11 C 0.87027(11) 0.0150(4) 0.4841(2) 0.0180(7) Uani 1 1 d . . .
C12 C 0.89105(11) 0.0421(4) 0.5709(2) 0.0168(7) Uani 1 1 d . . .
C13 C 0.93709(12) 0.1264(4) 0.5936(2) 0.0182(7) Uani 1 1 d . . .
H13 H 0.9494 0.1433 0.6519 0.022 Uiso 1 1 calc R . .
C14 C 0.80342(12) -0.0711(5) 0.3751(2) 0.0225(8) Uani 1 1 d . . .
H14A H 0.8241 -0.1540 0.3467 0.027 Uiso 1 1 calc R . .
H14B H 0.8034 0.0459 0.3465 0.027 Uiso 1 1 calc R . .
C15 C 0.75170(12) -0.1413(5) 0.3696(2) 0.0244(8) Uani 1 1 d . . .
H15 H 0.7465 -0.2501 0.3974 0.029 Uiso 1 1 calc R . .
C16 C 0.71273(14) -0.0589(6) 0.3279(2) 0.0380(10) Uani 1 1 d . . .
H16A H 0.7169 0.0501 0.2995 0.046 Uiso 1 1 calc R . .
H16B H 0.6808 -0.1092 0.3264 0.046 Uiso 1 1 calc R . .
C17 C 0.43847(11) 0.1501(4) 0.4007(2) 0.0185(7) Uani 1 1 d . . .
C18 C 0.43845(12) 0.1731(4) 0.4896(2) 0.0208(8) Uani 1 1 d . . .
C19 C 0.39649(12) 0.1354(5) 0.5301(2) 0.0257(8) Uani 1 1 d . . .
H19 H 0.3969 0.1505 0.5896 0.031 Uiso 1 1 calc R . .
C20 C 0.35427(13) 0.0748(5) 0.4779(2) 0.0279(9) Uani 1 1 d . . .
H20 H 0.3253 0.0490 0.5026 0.033 Uiso 1 1 calc R . .
C21 C 0.35382(12) 0.0510(5) 0.3887(2) 0.0269(8) Uani 1 1 d . . .
H21 H 0.3246 0.0089 0.3554 0.032 Uiso 1 1 calc R . .
C22 C 0.39566(12) 0.0886(5) 0.3489(2) 0.0234(8) Uani 1 1 d . . .
H22 H 0.3952 0.0733 0.2894 0.028 Uiso 1 1 calc R . .
C23 C 0.51249(12) 0.2553(4) 0.4533(2) 0.0197(8) Uani 1 1 d . . .
C24 C 0.56442(12) 0.3248(4) 0.4649(2) 0.0191(8) Uani 1 1 d . . .
C25 C 0.59054(12) 0.3525(4) 0.5479(2) 0.0208(8) Uani 1 1 d . . .
H25 H 0.5744 0.3277 0.5959 0.025 Uiso 1 1 calc R . .
C26 C 0.63933(12) 0.4153(5) 0.5609(2) 0.0215(8) Uani 1 1 d . . .
H26 H 0.6554 0.4338 0.6170 0.026 Uiso 1 1 calc R . .
C27 C 0.66479(12) 0.4512(4) 0.4908(2) 0.0214(8) Uani 1 1 d . . .
C28 C 0.63833(12) 0.4231(5) 0.4077(2) 0.0250(8) Uani 1 1 d . . .
C29 C 0.58897(12) 0.3661(5) 0.3948(2) 0.0243(8) Uani 1 1 d . . .
H29 H 0.5721 0.3554 0.3388 0.029 Uiso 1 1 calc R . .
C30 C 0.73864(13) 0.5542(5) 0.5814(2) 0.0296(9) Uani 1 1 d . . .
H30A H 0.7158 0.6145 0.6157 0.036 Uiso 1 1 calc R . .
H30B H 0.7664 0.6363 0.5763 0.036 Uiso 1 1 calc R . .
C31 C 0.75866(13) 0.3862(6) 0.6276(3) 0.0362(10) Uani 1 1 d . . .
H31 H 0.7727 0.3989 0.6853 0.043 Uiso 1 1 calc R . .
C32 C 0.75823(13) 0.2223(6) 0.5945(3) 0.0406(11) Uani 1 1 d . . .
H32A H 0.7445 0.2030 0.5370 0.049 Uiso 1 1 calc R . .
H32B H 0.7716 0.1255 0.6284 0.049 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
Ag1 N1 2.132(3) 2_756 ?
Ag1 N1 2.132(3) . ?
Ag2 N4 2.104(3) 2_655 ?
Ag2 N4 2.105(3) . ?
O1 C11 1.341(4) . ?
O1 C14 1.459(4) . ?
O2 N3 1.230(3) . ?
O3 N3 1.225(3) . ?
O4 C27 1.357(4) . ?
O4 C30 1.438(4) . ?
O5 N6 1.217(4) . ?
O6 N6 1.233(4) . ?
O7 N7 1.244(17) . ?
O7 N7 1.258(17) 2_655 ?
O8 N7 1.208(7) . ?
O9 N8 1.259(3) . ?
O10 N8 1.248(5) . ?
N1 C7 1.334(4) . ?
N1 C1 1.394(4) . ?
N2 C7 1.360(4) . ?
N2 C2 1.387(4) . ?
N3 C12 1.470(4) . ?
N4 C23 1.330(4) . ?
N4 C17 1.395(4) . ?
N5 C23 1.360(4) . ?
N5 C18 1.379(4) . ?
N6 C28 1.473(4) . ?
N7 O7 1.258(17) 2_655 ?
N8 O10 1.248(5) 2_755 ?
N8 O9 1.259(3) 2_755 ?
C1 C6 1.392(4) . ?
C1 C2 1.399(4) . ?
C2 C3 1.383(4) . ?
C3 C4 1.376(4) . ?
C4 C5 1.398(4) . ?
C5 C6 1.377(4) . ?
C7 C8 1.463(4) . ?
C8 C13 1.386(4) . ?
C8 C9 1.396(4) . ?
C9 C10 1.375(4) . ?
C10 C11 1.395(4) . ?
C11 C12 1.404(4) . ?
C12 C13 1.383(4) . ?
C14 C15 1.470(4) . ?
C15 C16 1.302(5) . ?
C17 C22 1.386(4) . ?
C17 C18 1.393(4) . ?
C18 C19 1.388(4) . ?
C19 C20 1.374(5) . ?
C20 C21 1.398(5) . ?
C21 C22 1.379(4) . ?
C23 C24 1.470(4) . ?
C24 C29 1.381(4) . ?
C24 C25 1.397(4) . ?
C25 C26 1.375(4) . ?
C26 C27 1.387(4) . ?
C27 C28 1.402(4) . ?
C28 C29 1.375(4) . ?
C30 C31 1.494(5) . ?
C31 C32 1.313(5) . ?

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 Ag1 N1 171.76(14) 2_756 . ?
N4 Ag2 N4 179.52(15) 2_655 . ?
C11 O1 C14 116.3(2) . . ?
C27 O4 C30 117.6(3) . . ?
N7 O7 N7 25.0(6) . 2_655 ?
C7 N1 C1 105.8(3) . . ?
C7 N1 Ag1 131.1(2) . . ?
C1 N1 Ag1 122.1(2) . . ?
C7 N2 C2 108.6(3) . . ?
O3 N3 O2 123.5(3) . . ?
O3 N3 C12 119.0(3) . . ?
O2 N3 C12 117.5(3) . . ?
C23 N4 C17 106.3(3) . . ?
C23 N4 Ag2 132.6(2) . . ?
C17 N4 Ag2 120.9(2) . . ?
C23 N5 C18 108.1(3) . . ?
O5 N6 O6 124.5(3) . . ?
O5 N6 C28 117.2(3) . . ?
O6 N6 C28 118.3(3) . . ?
O8 N7 O7 124.1(15) . . ?
O8 N7 O7 118.7(15) . 2_655 ?
O7 N7 O7 117.0(5) . 2_655 ?
O10 N8 O10 36.6(5) . 2_755 ?
O10 N8 O9 114.0(5) . . ?
O10 N8 O9 123.3(6) 2_755 . ?
O10 N8 O9 123.3(6) . 2_755 ?
O10 N8 O9 114.0(5) 2_755 2_755 ?
O9 N8 O9 119.5(4) . 2_755 ?
C6 C1 N1 129.7(3) . . ?
C6 C1 C2 120.5(3) . . ?
N1 C1 C2 109.8(3) . . ?
C3 C2 N2 132.8(3) . . ?
C3 C2 C1 122.5(3) . . ?
N2 C2 C1 104.7(3) . . ?
C4 C3 C2 116.2(3) . . ?
C3 C4 C5 122.1(3) . . ?
C6 C5 C4 121.5(3) . . ?
C5 C6 C1 117.1(3) . . ?
N1 C7 N2 111.1(3) . . ?
N1 C7 C8 125.7(3) . . ?
N2 C7 C8 123.2(3) . . ?
C13 C8 C9 117.5(3) . . ?
C13 C8 C7 121.2(3) . . ?
C9 C8 C7 121.3(3) . . ?
C10 C9 C8 121.8(3) . . ?
C9 C10 C11 121.5(3) . . ?
O1 C11 C10 124.6(3) . . ?
O1 C11 C12 119.0(3) . . ?
C10 C11 C12 116.3(3) . . ?
C13 C12 C11 122.2(3) . . ?
C13 C12 N3 116.1(3) . . ?
C11 C12 N3 121.7(3) . . ?
C12 C13 C8 120.6(3) . . ?
O1 C14 C15 108.0(3) . . ?
C16 C15 C14 123.4(4) . . ?
C22 C17 N4 130.8(3) . . ?
C22 C17 C18 120.4(3) . . ?
N4 C17 C18 108.7(3) . . ?
N5 C18 C19 131.9(3) . . ?
N5 C18 C17 105.8(3) . . ?
C19 C18 C17 122.3(3) . . ?
C20 C19 C18 116.6(3) . . ?
C19 C20 C21 121.6(3) . . ?
C22 C21 C20 121.5(3) . . ?
C21 C22 C17 117.5(3) . . ?
N4 C23 N5 111.0(3) . . ?
N4 C23 C24 127.2(3) . . ?
N5 C23 C24 121.8(3) . . ?
C29 C24 C25 117.7(3) . . ?
C29 C24 C23 121.5(3) . . ?
C25 C24 C23 120.8(3) . . ?
C26 C25 C24 122.1(3) . . ?
C25 C26 C27 120.4(3) . . ?
O4 C27 C26 125.1(3) . . ?
O4 C27 C28 117.7(3) . . ?
C26 C27 C28 117.1(3) . . ?
C29 C28 C27 122.4(3) . . ?
C29 C28 N6 116.9(3) . . ?
C27 C28 N6 120.6(3) . . ?
C28 C29 C24 120.2(3) . . ?
O4 C30 C31 112.7(3) . . ?
C32 C31 C30 126.1(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.094


_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1439671'
_audit_update_record             
;
2015-11-30 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H44 Cu F6 N8 O12 P'
_chemical_formula_weight         1181.46

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   'P2(1)/n  '

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                   15.2157(2)
_cell_length_b                   14.5593(2)
_cell_length_c                   22.9542(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.0210(10)
_cell_angle_gamma                90.00
_cell_volume                     4973.53(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26.80

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2424
_exptl_absorpt_coefficient_mu    0.569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8258
_exptl_absorpt_correction_T_max  0.9145
_exptl_absorpt_process_details   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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            94617
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         27.88
_reflns_number_total             11859
_reflns_number_gt                8664
_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. 
;

_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)+(0.0460P)²+3.5072P] 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         11859
_refine_ls_number_parameters     721
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
Cu1 Cu 0.266993(17) 0.252757(17) 0.010445(11) 0.01617(7) Uani 1 1 d . . .
P1 P 0.27547(4) 0.66930(4) 0.11339(3) 0.02448(14) Uani 1 1 d . . .
F1 F 0.24988(10) 0.58559(9) 0.06813(7) 0.0345(3) Uani 1 1 d . . .
F2 F 0.17117(10) 0.68827(13) 0.10890(8) 0.0562(5) Uani 1 1 d . . .
F3 F 0.30113(10) 0.75302(11) 0.15884(7) 0.0425(4) Uani 1 1 d . . .
F4 F 0.37940(10) 0.64875(12) 0.11817(9) 0.0565(5) Uani 1 1 d . . .
F5 F 0.27441(13) 0.60270(13) 0.16793(7) 0.0579(5) Uani 1 1 d . . .
F6 F 0.27564(16) 0.73653(12) 0.05937(8) 0.0684(6) Uani 1 1 d . . .
O1 O 0.02497(10) -0.08819(10) -0.09858(7) 0.0216(3) Uani 1 1 d . . .
O2 O 0.03213(12) 0.07190(12) -0.15026(7) 0.0320(4) Uani 1 1 d . . .
O3 O -0.01870(10) 0.16712(10) -0.09215(8) 0.0267(4) Uani 1 1 d . . .
O4 O 0.38176(11) 0.54852(11) -0.17711(7) 0.0258(4) Uani 1 1 d . . .
O5 O 0.33251(13) 0.70437(12) -0.12942(8) 0.0348(4) Uani 1 1 d . . .
O6 O 0.42829(13) 0.71899(11) -0.04527(8) 0.0354(4) Uani 1 1 d . . .
O7 O 0.52452(11) -0.08809(11) 0.14516(7) 0.0274(4) Uani 1 1 d . . .
O8 O 0.60785(11) 0.07496(12) 0.15141(8) 0.0342(4) Uani 1 1 d . . .
O9 O 0.49536(13) 0.16294(14) 0.15533(10) 0.0506(6) Uani 1 1 d . . .
O10 O 0.00451(10) 0.49005(11) 0.16132(7) 0.0230(3) Uani 1 1 d . . .
O11 O -0.16346(10) 0.49218(11) 0.08992(8) 0.0275(4) Uani 1 1 d . . .
O12 O -0.17672(10) 0.34900(11) 0.06346(8) 0.0291(4) Uani 1 1 d . . .
N1 N 0.24921(11) 0.19074(11) 0.08804(8) 0.0157(4) Uani 1 1 d . . .
N2 N 0.34992(11) 0.33696(11) 0.06507(8) 0.0164(4) Uani 1 1 d . . .
N3 N 0.16104(11) 0.30278(11) -0.05156(8) 0.0157(3) Uani 1 1 d . . .
N4 N 0.28087(11) 0.16425(12) -0.05566(8) 0.0164(4) Uani 1 1 d . . .
N5 N 0.02448(12) 0.09894(12) -0.10100(8) 0.0210(4) Uani 1 1 d . . .
N6 N 0.38096(13) 0.67265(12) -0.08457(9) 0.0237(4) Uani 1 1 d . . .
N7 N 0.52917(13) 0.09724(13) 0.13556(9) 0.0244(4) Uani 1 1 d . . .
N8 N -0.13356(12) 0.42055(12) 0.07449(8) 0.0200(4) Uani 1 1 d . . .
C1 C 0.30040(13) 0.23918(14) 0.13777(9) 0.0166(4) Uani 1 1 d . . .
C2 C 0.35297(14) 0.31375(14) 0.12609(9) 0.0168(4) Uani 1 1 d . . .
C3 C 0.40855(15) 0.35783(15) 0.17359(10) 0.0231(5) Uani 1 1 d . . .
H3 H 0.4458 0.4052 0.1662 0.028 Uiso 1 1 calc R . .
C4 C 0.40931(16) 0.33224(16) 0.23170(10) 0.0250(5) Uani 1 1 d . . .
H4 H 0.4472 0.3620 0.2630 0.030 Uiso 1 1 calc R . .
C5 C 0.35352(15) 0.26215(15) 0.24339(10) 0.0229(5) Uani 1 1 d . . .
H5 H 0.3526 0.2463 0.2825 0.027 Uiso 1 1 calc R . .
C6 C 0.29959(14) 0.21618(15) 0.19683(10) 0.0193(4) Uani 1 1 d . . .
H6 H 0.2622 0.1693 0.2048 0.023 Uiso 1 1 calc R . .
C7 C 0.17062(14) 0.27152(14) -0.10883(9) 0.0175(4) Uani 1 1 d . . .
C8 C 0.23060(14) 0.19867(14) -0.11091(9) 0.0179(4) Uani 1 1 d . . .
C9 C 0.24201(15) 0.16649(16) -0.16596(10) 0.0234(5) Uani 1 1 d . . .
H9 H 0.2823 0.1190 -0.1676 0.028 Uiso 1 1 calc R . .
C10 C 0.19398(16) 0.20459(17) -0.21823(10) 0.0278(5) Uani 1 1 d . . .
H10 H 0.2009 0.1818 -0.2548 0.033 Uiso 1 1 calc R . .
C11 C 0.13541(16) 0.27693(17) -0.21583(10) 0.0273(5) Uani 1 1 d . . .
H11 H 0.1032 0.3025 -0.2510 0.033 Uiso 1 1 calc R . .
C12 C 0.12467(15) 0.31112(16) -0.16163(10) 0.0229(5) Uani 1 1 d . . .
H12 H 0.0866 0.3608 -0.1604 0.027 Uiso 1 1 calc R . .
C13 C 0.22687(14) 0.10660(14) 0.09492(10) 0.0180(4) Uani 1 1 d . . .
H13 H 0.2469 0.0786 0.1317 0.022 Uiso 1 1 calc R . .
C14 C 0.17124(14) 0.05380(14) 0.04697(9) 0.0170(4) Uani 1 1 d . . .
C15 C 0.11768(13) 0.09857(14) -0.00144(9) 0.0162(4) Uani 1 1 d . . .
H15 H 0.1123 0.1622 -0.0014 0.019 Uiso 1 1 calc R . .
C16 C 0.07302(14) 0.04860(14) -0.04916(9) 0.0171(4) Uani 1 1 d . . .
C17 C 0.07558(14) -0.04820(14) -0.05036(10) 0.0181(4) Uani 1 1 d . . .
C18 C 0.12613(14) -0.09299(14) -0.00095(10) 0.0198(4) Uani 1 1 d . . .
H18 H 0.1284 -0.1568 0.0001 0.024 Uiso 1 1 calc R . .
C19 C 0.17322(14) -0.04221(14) 0.04685(10) 0.0194(4) Uani 1 1 d . . .
H19 H 0.2069 -0.0729 0.0795 0.023 Uiso 1 1 calc R . .
C20 C 0.01693(16) -0.18586(15) -0.10117(10) 0.0244(5) Uani 1 1 d . . .
H20A H -0.0101 -0.2080 -0.0691 0.029 Uiso 1 1 calc R . .
H20B H 0.0757 -0.2139 -0.0972 0.029 Uiso 1 1 calc R . .
C21 C -0.04089(16) -0.20972(17) -0.15987(11) 0.0283(5) Uani 1 1 d . . .
H21 H -0.0558 -0.2713 -0.1667 0.034 Uiso 1 1 calc R . .
C22 C -0.07268(16) -0.15160(18) -0.20285(11) 0.0301(5) Uani 1 1 d . . .
H22A H -0.0594 -0.0894 -0.1979 0.036 Uiso 1 1 calc R . .
H22B H -0.1084 -0.1727 -0.2382 0.036 Uiso 1 1 calc R . .
C23 C 0.37718(13) 0.41743(14) 0.05275(10) 0.0172(4) Uani 1 1 d . . .
H23 H 0.3961 0.4582 0.0840 0.021 Uiso 1 1 calc R . .
C24 C 0.37995(13) 0.44792(14) -0.00733(9) 0.0170(4) Uani 1 1 d . . .
C25 C 0.38287(13) 0.54174(14) -0.01863(10) 0.0172(4) Uani 1 1 d . . .
H25 H 0.3857 0.5836 0.0123 0.021 Uiso 1 1 calc R . .
C26 C 0.38156(14) 0.57274(14) -0.07548(10) 0.0185(4) Uani 1 1 d . . .
C27 C 0.38028(14) 0.51240(15) -0.12313(10) 0.0201(4) Uani 1 1 d . . .
C29 C 0.38033(14) 0.38693(14) -0.05450(10) 0.0201(4) Uani 1 1 d . . .
H29 H 0.3801 0.3240 -0.0475 0.024 Uiso 1 1 calc R . .
C30 C 0.40193(17) 0.48845(18) -0.22305(10) 0.0287(5) Uani 1 1 d . . .
H30A H 0.4485 0.4455 -0.2050 0.034 Uiso 1 1 calc R . .
H30B H 0.4253 0.5251 -0.2517 0.034 Uiso 1 1 calc R . .
C31 C 0.32170(17) 0.43544(18) -0.25518(11) 0.0320(6) Uani 1 1 d . . .
H31 H 0.2745 0.4255 -0.2359 0.038 Uiso 1 1 calc R . .
C32 C 0.31517(17) 0.40315(19) -0.30799(13) 0.0380(6) Uani 1 1 d . . .
H32A H 0.3615 0.4122 -0.3282 0.046 Uiso 1 1 calc R . .
H32B H 0.2641 0.3707 -0.3261 0.046 Uiso 1 1 calc R . .
C33 C 0.30697(14) 0.07982(15) -0.05368(10) 0.0191(4) Uani 1 1 d . . .
H33 H 0.2872 0.0437 -0.0873 0.023 Uiso 1 1 calc R . .
C34 C 0.36508(14) 0.03714(15) -0.00266(10) 0.0198(4) Uani 1 1 d . . .
C35 C 0.41824(14) 0.08846(15) 0.04300(10) 0.0195(4) Uani 1 1 d . . .
H35 H 0.4175 0.1523 0.0418 0.023 Uiso 1 1 calc R . .
C36 C 0.47150(14) 0.04263(15) 0.08954(10) 0.0199(4) Uani 1 1 d . . .
C37 C 0.47277(14) -0.05364(15) 0.09486(10) 0.0217(5) Uani 1 1 d . . .
C38 C 0.42037(15) -0.10399(15) 0.04947(11) 0.0244(5) Uani 1 1 d . . .
H38 H 0.4197 -0.1678 0.0515 0.029 Uiso 1 1 calc R . .
C39 C 0.36882(15) -0.05893(15) 0.00093(11) 0.0233(5) Uani 1 1 d . . .
H39 H 0.3358 -0.0935 -0.0301 0.028 Uiso 1 1 calc R . .
C40 C 0.51653(17) -0.18460(16) 0.15683(12) 0.0323(6) Uani 1 1 d . . .
H40A H 0.5427 -0.2206 0.1292 0.039 Uiso 1 1 calc R . .
H40B H 0.4537 -0.2014 0.1519 0.039 Uiso 1 1 calc R . .
C41 C 0.56476(18) -0.20289(19) 0.21909(13) 0.0362(6) Uani 1 1 d . . .
H41 H 0.5660 -0.2636 0.2318 0.043 Uiso 1 1 calc R . .
C42 C 0.60572(18) -0.1428(2) 0.25812(12) 0.0387(7) Uani 1 1 d . . .
H42A H 0.6065 -0.0811 0.2478 0.046 Uiso 1 1 calc R . .
H42B H 0.6339 -0.1620 0.2961 0.046 Uiso 1 1 calc R . .
C43 C 0.08418(14) 0.33621(13) -0.04673(9) 0.0165(4) Uani 1 1 d . . .
H43 H 0.0375 0.3351 -0.0801 0.020 Uiso 1 1 calc R . .
C44 C 0.06641(14) 0.37561(13) 0.00812(9) 0.0160(4) Uani 1 1 d . . .
C45 C -0.02214(14) 0.38040(13) 0.01597(9) 0.0169(4) Uani 1 1 d . . .
H45 H -0.0690 0.3581 -0.0133 0.020 Uiso 1 1 calc R . .
C46 C -0.03950(14) 0.41858(14) 0.06771(10) 0.0173(4) Uani 1 1 d . . .
C47 C 0.02886(14) 0.45437(14) 0.11269(10) 0.0181(4) Uani 1 1 d . . .
C48 C 0.11683(14) 0.44905(14) 0.10403(10) 0.0183(4) Uani 1 1 d . . .
H48 H 0.1639 0.4713 0.1331 0.022 Uiso 1 1 calc R . .
C49 C 0.13429(14) 0.41103(14) 0.05274(10) 0.0189(4) Uani 1 1 d . . .
H49 H 0.1933 0.4089 0.0477 0.023 Uiso 1 1 calc R . .
C50 C 0.07415(15) 0.52589(16) 0.20921(10) 0.0239(5) Uani 1 1 d . . .
H50A H 0.0469 0.5666 0.2338 0.029 Uiso 1 1 calc R . .
H50B H 0.1164 0.5616 0.1922 0.029 Uiso 1 1 calc R . .
C51 C 0.12394(16) 0.45169(16) 0.24739(10) 0.0250(5) Uani 1 1 d . . .
H51 H 0.0907 0.4054 0.2606 0.030 Uiso 1 1 calc R . .
C28 C 0.38101(15) 0.41832(15) -0.11090(10) 0.0230(5) Uani 1 1 d . . .
H28 H 0.3820 0.3764 -0.1413 0.028 Uiso 1 1 calc R . .
C52 C 0.21216(16) 0.44789(16) 0.26350(11) 0.0274(5) Uani 1 1 d . . .
H52A H 0.2472 0.4932 0.2510 0.033 Uiso 1 1 calc R . .
H52B H 0.2394 0.3999 0.2874 0.033 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
Cu1 N2 2.0021(17) . ?
Cu1 N4 2.0349(17) . ?
Cu1 N3 2.0493(17) . ?
Cu1 N1 2.0643(17) . ?
P1 F6 1.5802(18) . ?
P1 F5 1.5862(17) . ?
P1 F4 1.5906(16) . ?
P1 F2 1.5928(16) . ?
P1 F1 1.5963(14) . ?
P1 F3 1.5990(15) . ?
O1 C17 1.342(3) . ?
O1 C20 1.427(3) . ?
O2 N5 1.226(2) . ?
O3 N5 1.230(2) . ?
O4 C27 1.351(3) . ?
O4 C30 1.451(3) . ?
O5 N6 1.225(3) . ?
O6 N6 1.232(2) . ?
O7 C37 1.351(3) . ?
O7 C40 1.440(3) . ?
O8 N7 1.220(2) . ?
O9 N7 1.218(2) . ?
O10 C47 1.351(3) . ?
O10 C50 1.455(3) . ?
O11 N8 1.219(2) . ?
O12 N8 1.229(2) . ?
N1 C13 1.290(3) . ?
N1 C1 1.427(3) . ?
N2 C23 1.294(3) . ?
N2 C2 1.432(3) . ?
N3 C43 1.293(3) . ?
N3 C7 1.427(3) . ?
N4 C33 1.290(3) . ?
N4 C8 1.429(3) . ?
N5 C16 1.460(3) . ?
N6 C26 1.469(3) . ?
N7 C36 1.460(3) . ?
N8 C46 1.472(3) . ?
C1 C6 1.399(3) . ?
C1 C2 1.407(3) . ?
C2 C3 1.390(3) . ?
C3 C4 1.383(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.378(3) . ?
C7 C12 1.392(3) . ?
C7 C8 1.406(3) . ?
C8 C9 1.392(3) . ?
C9 C10 1.384(3) . ?
C10 C11 1.388(3) . ?
C11 C12 1.381(3) . ?
C13 C14 1.460(3) . ?
C14 C15 1.395(3) . ?
C14 C19 1.398(3) . ?
C15 C16 1.371(3) . ?
C16 C17 1.410(3) . ?
C17 C18 1.393(3) . ?
C18 C19 1.391(3) . ?
C20 C21 1.489(3) . ?
C21 C22 1.313(3) . ?
C23 C24 1.458(3) . ?
C24 C25 1.393(3) . ?
C24 C29 1.401(3) . ?
C25 C26 1.377(3) . ?
C26 C27 1.400(3) . ?
C27 C28 1.398(3) . ?
C29 C28 1.375(3) . ?
C30 C31 1.502(3) . ?
C31 C32 1.285(4) . ?
C33 C34 1.452(3) . ?
C34 C35 1.399(3) . ?
C34 C39 1.402(3) . ?
C35 C36 1.372(3) . ?
C36 C37 1.407(3) . ?
C37 C38 1.383(3) . ?
C38 C39 1.387(3) . ?
C40 C41 1.488(4) . ?
C41 C42 1.313(4) . ?
C43 C44 1.459(3) . ?
C44 C49 1.393(3) . ?
C44 C45 1.398(3) . ?
C45 C46 1.386(3) . ?
C46 C47 1.404(3) . ?
C47 C48 1.396(3) . ?
C48 C49 1.376(3) . ?
C50 C51 1.494(3) . ?
C51 C52 1.317(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N4 134.83(7) . . ?
N2 Cu1 N3 121.29(7) . . ?
N4 Cu1 N3 84.03(7) . . ?
N2 Cu1 N1 84.62(7) . . ?
N4 Cu1 N1 114.77(7) . . ?
N3 Cu1 N1 121.95(7) . . ?
F6 P1 F5 179.24(13) . . ?
F6 P1 F4 90.37(12) . . ?
F5 P1 F4 90.23(11) . . ?
F6 P1 F2 90.36(12) . . ?
F5 P1 F2 89.05(11) . . ?
F4 P1 F2 179.11(11) . . ?
F6 P1 F1 90.13(9) . . ?
F5 P1 F1 90.33(9) . . ?
F4 P1 F1 90.32(8) . . ?
F2 P1 F1 89.17(8) . . ?
F6 P1 F3 89.99(10) . . ?
F5 P1 F3 89.56(10) . . ?
F4 P1 F3 89.67(8) . . ?
F2 P1 F3 90.84(8) . . ?
F1 P1 F3 179.88(10) . . ?
C17 O1 C20 119.73(17) . . ?
C27 O4 C30 118.58(18) . . ?
C37 O7 C40 117.66(19) . . ?
C47 O10 C50 118.70(17) . . ?
C13 N1 C1 119.03(18) . . ?
C13 N1 Cu1 127.33(15) . . ?
C1 N1 Cu1 109.04(12) . . ?
C23 N2 C2 118.75(18) . . ?
C23 N2 Cu1 127.34(15) . . ?
C2 N2 Cu1 110.84(13) . . ?
C43 N3 C7 117.84(18) . . ?
C43 N3 Cu1 131.99(15) . . ?
C7 N3 Cu1 108.06(13) . . ?
C33 N4 C8 118.01(18) . . ?
C33 N4 Cu1 131.01(15) . . ?
C8 N4 Cu1 108.69(13) . . ?
O2 N5 O3 124.62(19) . . ?
O2 N5 C16 117.49(18) . . ?
O3 N5 C16 117.85(18) . . ?
O5 N6 O6 124.53(19) . . ?
O5 N6 C26 118.52(19) . . ?
O6 N6 C26 116.93(19) . . ?
O9 N7 O8 124.2(2) . . ?
O9 N7 C36 117.42(19) . . ?
O8 N7 C36 118.39(18) . . ?
O11 N8 O12 124.68(18) . . ?
O11 N8 C46 118.51(17) . . ?
O12 N8 C46 116.81(17) . . ?
C6 C1 C2 119.31(19) . . ?
C6 C1 N1 122.91(18) . . ?
C2 C1 N1 117.78(18) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 N2 123.28(19) . . ?
C1 C2 N2 117.68(18) . . ?
C4 C3 C2 120.9(2) . . ?
C3 C4 C5 120.1(2) . . ?
C6 C5 C4 119.8(2) . . ?
C5 C6 C1 120.7(2) . . ?
C12 C7 C8 119.6(2) . . ?
C12 C7 N3 122.74(19) . . ?
C8 C7 N3 117.60(18) . . ?
C9 C8 C7 119.3(2) . . ?
C9 C8 N4 122.9(2) . . ?
C7 C8 N4 117.75(18) . . ?
C10 C9 C8 120.6(2) . . ?
C9 C10 C11 119.8(2) . . ?
C12 C11 C10 120.4(2) . . ?
C11 C12 C7 120.2(2) . . ?
N1 C13 C14 122.28(19) . . ?
C15 C14 C19 118.34(19) . . ?
C15 C14 C13 120.36(19) . . ?
C19 C14 C13 121.24(19) . . ?
C16 C15 C14 119.89(19) . . ?
C15 C16 C17 122.3(2) . . ?
C15 C16 N5 117.84(18) . . ?
C17 C16 N5 119.80(19) . . ?
O1 C17 C18 126.38(19) . . ?
O1 C17 C16 115.86(19) . . ?
C18 C17 C16 117.7(2) . . ?
C19 C18 C17 119.98(19) . . ?
C18 C19 C14 121.7(2) . . ?
O1 C20 C21 107.43(19) . . ?
C22 C21 C20 125.8(2) . . ?
N2 C23 C24 123.81(19) . . ?
C25 C24 C29 118.17(19) . . ?
C25 C24 C23 118.90(19) . . ?
C29 C24 C23 122.93(19) . . ?
C26 C25 C24 120.2(2) . . ?
C25 C26 C27 122.00(19) . . ?
C25 C26 N6 117.23(19) . . ?
C27 C26 N6 120.77(19) . . ?
O4 C27 C28 124.4(2) . . ?
O4 C27 C26 118.18(19) . . ?
C28 C27 C26 117.4(2) . . ?
C28 C29 C24 121.3(2) . . ?
O4 C30 C31 113.2(2) . . ?
C32 C31 C30 123.1(2) . . ?
N4 C33 C34 124.6(2) . . ?
C35 C34 C39 118.6(2) . . ?
C35 C34 C33 122.4(2) . . ?
C39 C34 C33 119.0(2) . . ?
C36 C35 C34 118.6(2) . . ?
C35 C36 C37 123.2(2) . . ?
C35 C36 N7 117.84(19) . . ?
C37 C36 N7 119.0(2) . . ?
O7 C37 C38 126.1(2) . . ?
O7 C37 C36 116.0(2) . . ?
C38 C37 C36 117.9(2) . . ?
C37 C38 C39 119.7(2) . . ?
C38 C39 C34 121.9(2) . . ?
O7 C40 C41 108.0(2) . . ?
C42 C41 C40 127.3(2) . . ?
N3 C43 C44 123.76(19) . . ?
C49 C44 C45 118.27(19) . . ?
C49 C44 C43 122.52(19) . . ?
C45 C44 C43 119.19(19) . . ?
C46 C45 C44 119.4(2) . . ?
C45 C46 C47 122.33(19) . . ?
C45 C46 N8 117.50(19) . . ?
C47 C46 N8 120.18(18) . . ?
O10 C47 C48 125.10(19) . . ?
O10 C47 C46 117.49(18) . . ?
C48 C47 C46 117.40(19) . . ?
C49 C48 C47 120.4(2) . . ?
C48 C49 C44 122.15(19) . . ?
O10 C50 C51 112.60(18) . . ?
C52 C51 C50 123.9(2) . . ?
C29 C28 C27 120.9(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.070


_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether, acetone'
####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1439672'
_audit_update_record             
;
2015-11-30 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H49 B Cu F4 N9 O14'
_chemical_formula_weight         1150.33

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'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   14.5499(2)
_cell_length_b                   18.8640(2)
_cell_length_c                   19.3788(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.3780(10)
_cell_angle_gamma                90
_cell_volume                     5128.45(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9880
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      24.36

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             2376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.517
_shelx_estimated_absorpt_T_min   0.801
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6876
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            89433
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.534
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10493
_reflns_number_gt                8312
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0312P)²+4.4935P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10493
_refine_ls_number_parameters     769
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0857
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.25050(2) 0.19876(2) 0.25236(2) 0.01715(7) Uani 1 1 d . . . . .
F1 F 0.30517(9) 0.48462(7) 0.42265(7) 0.0362(3) Uani 1 1 d . . . . .
F2 F 0.20912(11) 0.49212(7) 0.49722(7) 0.0437(4) Uani 1 1 d . . . . .
F3 F 0.28876(10) 0.39024(7) 0.49048(7) 0.0353(3) Uani 1 1 d . . . . .
F4 F 0.16534(9) 0.42414(7) 0.39718(7) 0.0349(3) Uani 1 1 d . . . . .
O1 O 0.06226(10) 0.11334(7) -0.09410(7) 0.0226(3) Uani 1 1 d . . . . .
O2 O 0.03913(11) 0.23306(8) -0.17097(7) 0.0272(3) Uani 1 1 d . . . . .
O3 O 0.16884(10) 0.29157(8) -0.12360(8) 0.0280(3) Uani 1 1 d . . . . .
O4 O 0.34134(11) -0.00231(7) 0.37856(7) 0.0269(3) Uani 1 1 d . . . . .
O5 O 0.40913(10) -0.04462(7) 0.48284(7) 0.0239(3) Uani 1 1 d . . . . .
O6 O 0.41429(12) 0.03352(8) 0.59098(7) 0.0316(4) Uani 1 1 d . . . . .
O7 O 0.11514(12) 0.25994(8) 0.56252(8) 0.0344(4) Uani 1 1 d . . . . .
N5A N 0.1450(4) 0.1192(4) 0.5805(3) 0.0231(13) Uani 0.6 1 d D . P A 1
O8A O 0.21697(18) 0.08431(16) 0.60472(16) 0.0314(6) Uani 0.6 1 d D . P A 1
O9A O 0.0855(2) 0.13225(18) 0.61265(17) 0.0402(7) Uani 0.6 1 d D . P A 1
N5B N 0.1147(6) 0.1161(6) 0.5751(5) 0.048(4) Uani 0.4 1 d D . P A 2
O8B O 0.1848(6) 0.1232(3) 0.6258(3) 0.069(2) Uani 0.4 1 d D . P A 2
O9B O 0.0457(3) 0.0794(3) 0.5754(3) 0.0569(16) Uani 0.4 1 d D . P A 2
O10 O 0.41760(14) 0.39289(9) 0.17694(9) 0.0424(5) Uani 1 1 d . . . . .
O11 O 0.33218(15) 0.43348(9) 0.07504(10) 0.0491(5) Uani 1 1 d . . . . .
O12 O 0.37736(12) 0.36372(8) -0.02860(9) 0.0347(4) Uani 1 1 d . . . . .
O13 O 0.50930(12) 0.78274(11) 0.25944(9) 0.0498(5) Uani 1 1 d . . . . .
O14 O 0.63294(19) 0.71782(12) 0.27431(16) 0.0853(9) Uani 1 1 d . . . . .
N1 N 0.10341(12) 0.25206(9) -0.11948(9) 0.0212(4) Uani 1 1 d . . . . .
N2 N 0.18919(11) 0.28935(8) 0.20010(8) 0.0166(3) Uani 1 1 d . . . . .
N3 N 0.31960(11) 0.26596(8) 0.33309(8) 0.0161(3) Uani 1 1 d . . . . .
N4 N 0.37724(11) 0.00523(8) 0.44320(8) 0.0176(3) Uani 1 1 d . . . . .
N6 N 0.18113(11) 0.11124(8) 0.27861(8) 0.0163(3) Uani 1 1 d . . . . .
N7 N 0.31098(11) 0.12827(8) 0.19535(8) 0.0167(3) Uani 1 1 d . . . . .
N8 N 0.37562(15) 0.38555(10) 0.11347(11) 0.0331(5) Uani 1 1 d . . . . .
N9 N 0.58842(16) 0.77018(12) 0.25178(11) 0.0404(5) Uani 1 1 d . . . . .
C1 C 0.07318(17) -0.06038(12) -0.15438(13) 0.0339(5) Uani 1 1 d . . . . .
H1A H 0.1045 -0.0832 -0.1122 0.041 Uiso 1 1 calc R U . . .
H1B H 0.0690 -0.0820 -0.1983 0.041 Uiso 1 1 calc R U . . .
C2 C 0.03486(15) 0.00239(11) -0.15206(11) 0.0251(5) Uani 1 1 d . . . . .
H2 H 0.0039 0.0242 -0.1950 0.030 Uiso 1 1 calc R U . . .
C3 C 0.03871(15) 0.04010(10) -0.08399(11) 0.0224(4) Uani 1 1 d . . . . .
H3A H -0.0224 0.0372 -0.0729 0.027 Uiso 1 1 calc R U . . .
H3B H 0.0869 0.0191 -0.0449 0.027 Uiso 1 1 calc R U . . .
C4 C 0.07797(13) 0.15729(10) -0.03738(10) 0.0189(4) Uani 1 1 d . . . . .
C5 C 0.10188(13) 0.22775(11) -0.04794(10) 0.0187(4) Uani 1 1 d . . . . .
C6 C 0.12580(13) 0.27576(10) 0.00747(10) 0.0189(4) Uani 1 1 d . . . . .
H6 H 0.1423 0.3219 -0.0011 0.023 Uiso 1 1 calc R U . . .
C7 C 0.12528(13) 0.25519(10) 0.07634(10) 0.0180(4) Uani 1 1 d . . . . .
C8 C 0.09785(14) 0.18590(10) 0.08703(10) 0.0194(4) Uani 1 1 d . . . . .
H8 H 0.0949 0.1720 0.1324 0.023 Uiso 1 1 calc R U . . .
C9 C 0.07505(14) 0.13776(10) 0.03143(10) 0.0197(4) Uani 1 1 d . . . . .
H9 H 0.0576 0.0918 0.0399 0.024 Uiso 1 1 calc R U . . .
C10 C 0.15378(13) 0.30657(10) 0.13478(10) 0.0186(4) Uani 1 1 d . . . . .
H10 H 0.1456 0.3545 0.1236 0.022 Uiso 1 1 calc R U . . .
C11 C 0.21289(14) 0.34800(10) 0.25198(10) 0.0194(4) Uani 1 1 d . . . . .
H11A H 0.1671 0.3496 0.2803 0.023 Uiso 1 1 calc R U . . .
H11B H 0.2098 0.3927 0.2267 0.023 Uiso 1 1 calc R U . . .
C12 C 0.31236(14) 0.33734(10) 0.30059(10) 0.0192(4) Uani 1 1 d . . . . .
H12A H 0.3590 0.3422 0.2732 0.023 Uiso 1 1 calc R U . . .
H12B H 0.3255 0.3731 0.3379 0.023 Uiso 1 1 calc R U . . .
C13 C 0.35227(13) 0.26472(10) 0.40092(10) 0.0175(4) Uani 1 1 d . . . . .
H13 H 0.3684 0.3083 0.4233 0.021 Uiso 1 1 calc R U . . .
C14 C 0.36716(13) 0.20236(10) 0.44745(10) 0.0180(4) Uani 1 1 d . . . . .
C15 C 0.36709(13) 0.13266(10) 0.42398(10) 0.0164(4) Uani 1 1 d . . . . .
H15 H 0.3574 0.1233 0.3754 0.020 Uiso 1 1 calc R U . . .
C16 C 0.38139(13) 0.07715(10) 0.47223(10) 0.0176(4) Uani 1 1 d . . . . .
C17 C 0.39844(15) 0.08913(11) 0.54646(11) 0.0242(5) Uani 1 1 d . . . . .
C18 C 0.39797(17) 0.15938(12) 0.56894(11) 0.0300(5) Uani 1 1 d . . . . .
H18 H 0.4083 0.1692 0.6174 0.036 Uiso 1 1 calc R U . . .
C19 C 0.38253(15) 0.21430(11) 0.52081(11) 0.0247(5) Uani 1 1 d . . . . .
H19 H 0.3823 0.2606 0.5374 0.030 Uiso 1 1 calc R U . . .
C20 C 0.4331(2) 0.04642(12) 0.66656(11) 0.0359(6) Uani 1 1 d . . . . .
H20A H 0.3774 0.0669 0.6774 0.043 Uiso 1 1 calc R U . . .
H20B H 0.4859 0.0793 0.6820 0.043 Uiso 1 1 calc R U . . .
C21 C 0.45699(16) -0.02230(12) 0.70393(11) 0.0276(5) Uani 1 1 d . . . . .
H21 H 0.4682 -0.0223 0.7535 0.033 Uiso 1 1 calc R U . . .
C22 C 0.46354(15) -0.08315(12) 0.67280(12) 0.0293(5) Uani 1 1 d . . . . .
H22A H 0.4528 -0.0853 0.6234 0.035 Uiso 1 1 calc R U . . .
H22B H 0.4789 -0.1241 0.7002 0.035 Uiso 1 1 calc R U . . .
C23A C 0.1848(4) 0.3918(4) 0.6850(4) 0.0412(16) Uani 0.4 1 d D . P B 3
H23A H 0.2325 0.4111 0.6670 0.049 Uiso 0.4 1 calc R U P B 3
H23B H 0.1840 0.4009 0.7320 0.049 Uiso 0.4 1 calc R U P B 3
C24A C 0.1173(11) 0.3511(4) 0.6434(5) 0.0326(7) Uani 0.4 1 d D . P B 3
H24A H 0.069(5) 0.341(4) 0.662(4) 0.039 Uiso 0.4 1 d . U P C 3
C43A C 0.3551(6) 0.4294(6) -0.1340(6) 0.0326(7) Uani 0.4 1 d D . P D 3
H43A H 0.296(4) 0.456(3) -0.123(3) 0.039 Uiso 0.4 1 d . U P E 3
C44A C 0.4078(5) 0.4634(3) -0.1675(3) 0.0308(13) Uani 0.4 1 d D . P D 3
H44A H 0.4630 0.4426 -0.1736 0.037 Uiso 0.4 1 calc R U P D 3
H44B H 0.3902 0.5086 -0.1854 0.037 Uiso 0.4 1 calc R U P D 3
C23B C 0.1068(3) 0.3259(3) 0.6820(2) 0.0377(11) Uani 0.6 1 d D . P B 4
H23D H 0.0931 0.2780 0.6736 0.045 Uiso 0.6 1 calc R U P B 4
H23C H 0.1091 0.3455 0.7265 0.045 Uiso 0.6 1 calc R U P B 4
C24B C 0.1226(7) 0.3656(3) 0.6314(3) 0.0326(7) Uani 0.6 1 d D . P B 4
H24B H 0.142(3) 0.412(2) 0.637(2) 0.039 Uiso 0.6 1 d . U P F 4
C43B C 0.3824(4) 0.4262(4) -0.1335(4) 0.0326(7) Uani 0.6 1 d D . P D 4
H43B H 0.432(3) 0.448(2) -0.107(2) 0.039 Uiso 0.6 1 d . U P G 4
C44B C 0.3232(4) 0.4485(3) -0.1939(3) 0.0543(13) Uani 0.6 1 d D . P D 4
H44C H 0.2753 0.4187 -0.2195 0.065 Uiso 0.6 1 calc R U P D 4
H44D H 0.3296 0.4939 -0.2106 0.065 Uiso 0.6 1 calc R U P D 4
C25 C 0.11912(18) 0.33566(12) 0.56266(13) 0.0363(6) Uani 1 1 d D . . . .
H25A H 0.0644 0.3561 0.5285 0.044 Uiso 1 1 calc R U . B 3
H25B H 0.1772 0.3529 0.5529 0.044 Uiso 1 1 calc R U . B 3
C26 C 0.12031(14) 0.22482(11) 0.50297(11) 0.0243(4) Uani 1 1 d . . . . .
C27 C 0.12863(16) 0.15135(12) 0.50911(11) 0.0278(5) Uani 1 1 d . . . . .
C28 C 0.13497(16) 0.10884(11) 0.45307(11) 0.0282(5) Uani 1 1 d . . . . .
H28 H 0.1393 0.0599 0.4588 0.034 Uiso 1 1 calc R U . . .
C29 C 0.13483(14) 0.13936(10) 0.38736(11) 0.0196(4) Uani 1 1 d . . . . .
C30 C 0.12633(13) 0.21298(10) 0.38078(11) 0.0196(4) Uani 1 1 d . . . . .
H30 H 0.1257 0.2341 0.3373 0.023 Uiso 1 1 calc R U . . .
C31 C 0.11890(14) 0.25522(11) 0.43746(11) 0.0224(4) Uani 1 1 d . . . . .
H31 H 0.1129 0.3041 0.4316 0.027 Uiso 1 1 calc R U . . .
C32 C 0.14869(14) 0.09242(10) 0.33090(10) 0.0195(4) Uani 1 1 d . . . . .
H32 H 0.1325 0.0450 0.3333 0.023 Uiso 1 1 calc R U . . .
C33 C 0.19620(14) 0.05340(10) 0.23156(10) 0.0188(4) Uani 1 1 d . . . . .
H33A H 0.1509 0.0576 0.1849 0.023 Uiso 1 1 calc R U . . .
H33B H 0.1864 0.0079 0.2519 0.023 Uiso 1 1 calc R U . . .
C34 C 0.29708(14) 0.05797(10) 0.22395(10) 0.0177(4) Uani 1 1 d . . . . .
H34A H 0.3424 0.0511 0.2702 0.021 Uiso 1 1 calc R U . . .
H34B H 0.3074 0.0213 0.1918 0.021 Uiso 1 1 calc R U . . .
C35 C 0.34065(13) 0.12769(10) 0.13898(10) 0.0179(4) Uani 1 1 d . . . . .
H35 H 0.3536 0.0837 0.1221 0.022 Uiso 1 1 calc R U . . .
C36 C 0.35613(13) 0.18985(10) 0.09857(10) 0.0188(4) Uani 1 1 d . . . . .
C37 C 0.36717(14) 0.25823(10) 0.12633(11) 0.0199(4) Uani 1 1 d . . . . .
H37 H 0.3709 0.2659 0.1744 0.024 Uiso 1 1 calc R U . . .
C38 C 0.37254(15) 0.31453(10) 0.08234(12) 0.0239(5) Uani 1 1 d . . . . .
C39 C 0.37097(15) 0.30565(11) 0.00977(12) 0.0243(4) Uani 1 1 d . . . . .
C40 C 0.36559(15) 0.23636(11) -0.01606(11) 0.0238(4) Uani 1 1 d . . . . .
H40 H 0.3677 0.2280 -0.0629 0.029 Uiso 1 1 calc R U . . .
C41 C 0.35725(14) 0.18015(11) 0.02720(11) 0.0213(4) Uani 1 1 d . . . . .
H41 H 0.3522 0.1345 0.0085 0.026 Uiso 1 1 calc R U . . .
C42 C 0.37794(17) 0.35514(12) -0.10271(12) 0.0292(5) Uani 1 1 d D . . . .
H42A H 0.3300 0.3213 -0.1269 0.035 Uiso 1 1 calc R U . D 3
H42B H 0.4399 0.3394 -0.1065 0.035 Uiso 1 1 calc R U . D 3
C45 C 0.63156(17) 0.82259(12) 0.21329(12) 0.0299(5) Uani 1 1 d . . . . .
C46 C 0.72835(18) 0.82040(13) 0.22352(14) 0.0378(6) Uani 1 1 d . . . . .
H46 H 0.7654 0.7862 0.2527 0.045 Uiso 1 1 calc R U . . .
C47 C 0.7692(2) 0.87085(14) 0.18888(16) 0.0477(7) Uani 1 1 d . . . . .
H47 H 0.8349 0.8712 0.1953 0.057 Uiso 1 1 calc R U . . .
C48 C 0.7131(3) 0.92035(15) 0.14507(15) 0.0537(8) Uani 1 1 d . . . . .
H48 H 0.7410 0.9537 0.1216 0.064 Uiso 1 1 calc R U . . .
C49 C 0.6158(2) 0.92088(14) 0.13567(14) 0.0504(8) Uani 1 1 d . . . . .
H49 H 0.5784 0.9542 0.1055 0.060 Uiso 1 1 calc R U . . .
C50 C 0.57354(19) 0.87209(14) 0.17092(13) 0.0399(6) Uani 1 1 d . . . . .
H50 H 0.5082 0.8728 0.1661 0.048 Uiso 1 1 calc R U . . .
B1 B 0.24169(18) 0.44778(13) 0.45203(13) 0.0243(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 2.0571(16) . ?
Cu1 N2 2.0645(16) . ?
Cu1 N6 2.0677(16) . ?
Cu1 N7 2.0684(16) . ?
F1 B1 1.393(3) . ?
F2 B1 1.382(3) . ?
F3 B1 1.390(3) . ?
F4 B1 1.392(3) . ?
O1 C4 1.347(2) . ?
O1 C3 1.449(2) . ?
O2 N1 1.226(2) . ?
O3 N1 1.228(2) . ?
O4 N4 1.231(2) . ?
O5 N4 1.225(2) . ?
O6 C17 1.339(2) . ?
O6 C20 1.438(2) . ?
O7 C26 1.350(2) . ?
O7 C25 1.430(3) . ?
N5A O9A 1.218(4) . ?
N5A O8A 1.220(4) . ?
N5A C27 1.472(6) . ?
N5B O8B 1.221(5) . ?
N5B O9B 1.222(5) . ?
N5B C27 1.502(9) . ?
O10 N8 1.228(3) . ?
O11 N8 1.234(3) . ?
O12 C39 1.341(2) . ?
O12 C42 1.448(3) . ?
O13 N9 1.222(3) . ?
O14 N9 1.198(3) . ?
N1 C5 1.466(2) . ?
N2 C10 1.276(2) . ?
N2 C11 1.473(2) . ?
N3 C13 1.274(2) . ?
N3 C12 1.478(2) . ?
N4 C16 1.464(2) . ?
N6 C32 1.276(2) . ?
N6 C33 1.475(2) . ?
N7 C35 1.277(2) . ?
N7 C34 1.472(2) . ?
N8 C38 1.465(3) . ?
N9 C45 1.475(3) . ?
C1 C2 1.315(3) . ?
C1 H1A 0.9300 . ?
C1 H1B 0.9300 . ?
C2 C3 1.487(3) . ?
C2 H2 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.395(3) . ?
C4 C5 1.403(3) . ?
C5 C6 1.377(3) . ?
C6 C7 1.392(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.398(3) . ?
C7 C10 1.464(3) . ?
C8 C9 1.381(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.516(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.463(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(3) . ?
C14 C19 1.398(3) . ?
C15 C16 1.382(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.412(3) . ?
C17 C18 1.396(3) . ?
C18 C19 1.372(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.481(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.312(3) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9300 . ?
C22 H22B 0.9300 . ?
C23A C24A 1.337(11) . ?
C23A H23A 0.9300 . ?
C23A H23B 0.9300 . ?
C24A C25 1.598(10) . ?
C24A H24A 0.89(8) . ?
C43A C44A 1.299(12) . ?
C43A C42 1.528(11) . ?
C43A H43A 1.07(6) . ?
C44A H44A 0.9300 . ?
C44A H44B 0.9300 . ?
C23B C24B 1.300(7) . ?
C23B H23D 0.9300 . ?
C23B H23C 0.9300 . ?
C24B C25 1.436(6) . ?
C24B H24B 0.91(5) . ?
C43B C44B 1.322(8) . ?
C43B C42 1.476(8) . ?
C43B H43B 0.87(4) . ?
C44B H44C 0.9300 . ?
C44B H44D 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C31 1.388(3) . ?
C26 C27 1.394(3) . ?
C27 C28 1.373(3) . ?
C28 C29 1.397(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.397(3) . ?
C29 C32 1.463(3) . ?
C30 C31 1.384(3) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C34 1.516(3) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.460(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.390(3) . ?
C36 C41 1.400(3) . ?
C37 C38 1.377(3) . ?
C37 H37 0.9300 . ?
C38 C39 1.410(3) . ?
C39 C40 1.394(3) . ?
C40 C41 1.377(3) . ?
C40 H40 0.9300 . ?
C41 H41 0.9300 . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C45 C46 1.370(3) . ?
C45 C50 1.375(3) . ?
C46 C47 1.386(4) . ?
C46 H46 0.9300 . ?
C47 C48 1.376(4) . ?
C47 H47 0.9300 . ?
C48 C49 1.378(4) . ?
C48 H48 0.9300 . ?
C49 C50 1.384(4) . ?
C49 H49 0.9300 . ?
C50 H50 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
N3 Cu1 N2 85.61(6) . . ?
N3 Cu1 N6 118.49(6) . . ?
N2 Cu1 N6 127.30(6) . . ?
N3 Cu1 N7 127.66(6) . . ?
N2 Cu1 N7 117.37(6) . . ?
N6 Cu1 N7 85.57(6) . . ?
C4 O1 C3 118.13(15) . . ?
C17 O6 C20 118.52(16) . . ?
C26 O7 C25 118.72(18) . . ?
O9A N5A O8A 124.5(5) . . ?
O9A N5A C27 115.9(4) . . ?
O8A N5A C27 119.5(4) . . ?
O8B N5B O9B 124.8(9) . . ?
O8B N5B C27 111.3(5) . . ?
O9B N5B C27 123.5(7) . . ?
C39 O12 C42 118.57(16) . . ?
O2 N1 O3 124.17(17) . . ?
O2 N1 C5 118.59(16) . . ?
O3 N1 C5 117.23(16) . . ?
C10 N2 C11 116.47(16) . . ?
C10 N2 Cu1 134.89(14) . . ?
C11 N2 Cu1 107.13(11) . . ?
C13 N3 C12 114.92(16) . . ?
C13 N3 Cu1 138.31(14) . . ?
C12 N3 Cu1 105.79(11) . . ?
O5 N4 O4 122.52(16) . . ?
O5 N4 C16 120.02(15) . . ?
O4 N4 C16 117.46(15) . . ?
C32 N6 C33 115.58(16) . . ?
C32 N6 Cu1 136.45(14) . . ?
C33 N6 Cu1 106.04(11) . . ?
C35 N7 C34 115.21(16) . . ?
C35 N7 Cu1 138.66(14) . . ?
C34 N7 Cu1 104.94(11) . . ?
O10 N8 O11 124.2(2) . . ?
O10 N8 C38 117.93(19) . . ?
O11 N8 C38 117.8(2) . . ?
O14 N9 O13 123.4(2) . . ?
O14 N9 C45 118.4(2) . . ?
O13 N9 C45 118.2(2) . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C1 C2 C3 123.0(2) . . ?
C1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
O1 C3 C2 106.91(16) . . ?
O1 C3 H3A 110.3 . . ?
C2 C3 H3A 110.3 . . ?
O1 C3 H3B 110.3 . . ?
C2 C3 H3B 110.3 . . ?
H3A C3 H3B 108.6 . . ?
O1 C4 C9 125.17(18) . . ?
O1 C4 C5 117.33(17) . . ?
C9 C4 C5 117.47(18) . . ?
C6 C5 C4 122.06(18) . . ?
C6 C5 N1 117.88(17) . . ?
C4 C5 N1 120.06(17) . . ?
C5 C6 C7 119.99(18) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 118.49(18) . . ?
C6 C7 C10 118.99(17) . . ?
C8 C7 C10 122.53(18) . . ?
C9 C8 C7 121.22(18) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C4 120.70(18) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
N2 C10 C7 123.76(18) . . ?
N2 C10 H10 118.1 . . ?
C7 C10 H10 118.1 . . ?
N2 C11 C12 109.66(15) . . ?
N2 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
N2 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N3 C12 C11 109.51(15) . . ?
N3 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
N3 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
N3 C13 C14 127.20(18) . . ?
N3 C13 H13 116.4 . . ?
C14 C13 H13 116.4 . . ?
C15 C14 C19 118.09(18) . . ?
C15 C14 C13 124.85(17) . . ?
C19 C14 C13 117.06(17) . . ?
C16 C15 C14 120.53(18) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 121.48(18) . . ?
C15 C16 N4 117.30(16) . . ?
C17 C16 N4 121.21(17) . . ?
O6 C17 C18 123.86(18) . . ?
O6 C17 C16 119.00(18) . . ?
C18 C17 C16 117.13(18) . . ?
C19 C18 C17 121.21(19) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C14 121.53(19) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
O6 C20 C21 107.86(18) . . ?
O6 C20 H20A 110.1 . . ?
C21 C20 H20A 110.1 . . ?
O6 C20 H20B 110.1 . . ?
C21 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
C22 C21 C20 125.3(2) . . ?
C22 C21 H21 117.4 . . ?
C20 C21 H21 117.4 . . ?
C21 C22 H22A 120.0 . . ?
C21 C22 H22B 120.0 . . ?
H22A C22 H22B 120.0 . . ?
C24A C23A H23A 120.0 . . ?
C24A C23A H23B 120.0 . . ?
H23A C23A H23B 120.0 . . ?
C23A C24A C25 119.7(9) . . ?
C23A C24A H24A 114(5) . . ?
C25 C24A H24A 125(5) . . ?
C44A C43A C42 123.8(6) . . ?
C44A C43A H43A 119(3) . . ?
C42 C43A H43A 117(3) . . ?
C43A C44A H44A 120.0 . . ?
C43A C44A H44B 120.0 . . ?
H44A C44A H44B 120.0 . . ?
C24B C23B H23D 120.0 . . ?
C24B C23B H23C 120.0 . . ?
H23D C23B H23C 120.0 . . ?
C23B C24B C25 120.2(4) . . ?
C23B C24B H24B 125(3) . . ?
C25 C24B H24B 115(3) . . ?
C44B C43B C42 123.9(5) . . ?
C44B C43B H43B 127(3) . . ?
C42 C43B H43B 109(3) . . ?
C43B C44B H44C 120.0 . . ?
C43B C44B H44D 120.0 . . ?
H44C C44B H44D 120.0 . . ?
O7 C25 C24B 112.7(3) . . ?
O7 C25 C24A 99.9(3) . . ?
O7 C25 H25A 111.8 . . ?
C24A C25 H25A 111.8 . . ?
O7 C25 H25B 111.8 . . ?
C24A C25 H25B 111.8 . . ?
H25A C25 H25B 109.5 . . ?
O7 C26 C31 126.04(19) . . ?
O7 C26 C27 115.99(19) . . ?
C31 C26 C27 117.96(19) . . ?
C28 C27 C26 122.4(2) . . ?
C28 C27 N5A 118.3(3) . . ?
C26 C27 N5A 118.7(4) . . ?
C28 C27 N5B 117.9(5) . . ?
C26 C27 N5B 119.0(5) . . ?
C27 C28 C29 119.8(2) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
C28 C29 C30 118.13(19) . . ?
C28 C29 C32 117.72(18) . . ?
C30 C29 C32 124.06(18) . . ?
C31 C30 C29 121.56(19) . . ?
C31 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
C30 C31 C26 120.17(19) . . ?
C30 C31 H31 119.9 . . ?
C26 C31 H31 119.9 . . ?
N6 C32 C29 125.37(18) . . ?
N6 C32 H32 117.3 . . ?
C29 C32 H32 117.3 . . ?
N6 C33 C34 108.93(15) . . ?
N6 C33 H33A 109.9 . . ?
C34 C33 H33A 109.9 . . ?
N6 C33 H33B 109.9 . . ?
C34 C33 H33B 109.9 . . ?
H33A C33 H33B 108.3 . . ?
N7 C34 C33 108.73(15) . . ?
N7 C34 H34A 109.9 . . ?
C33 C34 H34A 109.9 . . ?
N7 C34 H34B 109.9 . . ?
C33 C34 H34B 109.9 . . ?
H34A C34 H34B 108.3 . . ?
N7 C35 C36 125.96(18) . . ?
N7 C35 H35 117.0 . . ?
C36 C35 H35 117.0 . . ?
C37 C36 C41 118.24(18) . . ?
C37 C36 C35 123.77(18) . . ?
C41 C36 C35 117.96(17) . . ?
C38 C37 C36 119.72(19) . . ?
C38 C37 H37 120.1 . . ?
C36 C37 H37 120.1 . . ?
C37 C38 C39 122.48(18) . . ?
C37 C38 N8 116.81(18) . . ?
C39 C38 N8 120.66(18) . . ?
O12 C39 C40 124.90(19) . . ?
O12 C39 C38 118.07(18) . . ?
C40 C39 C38 117.00(18) . . ?
C41 C40 C39 120.59(19) . . ?
C41 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
C40 C41 C36 121.81(19) . . ?
C40 C41 H41 119.1 . . ?
C36 C41 H41 119.1 . . ?
O12 C42 C43B 108.2(3) . . ?
O12 C42 C43A 103.5(4) . . ?
O12 C42 H42A 111.1 . . ?
C43A C42 H42A 111.1 . . ?
O12 C42 H42B 111.1 . . ?
C43A C42 H42B 111.1 . . ?
H42A C42 H42B 109.0 . . ?
C46 C45 C50 123.5(2) . . ?
C46 C45 N9 117.8(2) . . ?
C50 C45 N9 118.7(2) . . ?
C45 C46 C47 117.8(3) . . ?
C45 C46 H46 121.1 . . ?
C47 C46 H46 121.1 . . ?
C48 C47 C46 120.3(3) . . ?
C48 C47 H47 119.9 . . ?
C46 C47 H47 119.9 . . ?
C47 C48 C49 120.5(3) . . ?
C47 C48 H48 119.8 . . ?
C49 C48 H48 119.8 . . ?
C48 C49 C50 120.3(3) . . ?
C48 C49 H49 119.8 . . ?
C50 C49 H49 119.8 . . ?
C45 C50 C49 117.6(3) . . ?
C45 C50 H50 121.2 . . ?
C49 C50 H50 121.2 . . ?
F2 B1 F3 109.63(18) . . ?
F2 B1 F4 109.84(19) . . ?
F3 B1 F4 109.83(18) . . ?
F2 B1 F1 109.45(19) . . ?
F3 B1 F1 108.84(19) . . ?
F4 B1 F1 109.22(18) . . ?

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
C4 O1 C3 C2 -174.41(16) . . . . ?
C1 C2 C3 O1 136.1(2) . . . . ?
C3 O1 C4 C9 1.2(3) . . . . ?
C3 O1 C4 C5 179.19(17) . . . . ?
O1 C4 C5 C6 -175.41(17) . . . . ?
C9 C4 C5 C6 2.8(3) . . . . ?
O1 C4 C5 N1 3.6(3) . . . . ?
C9 C4 C5 N1 -178.20(17) . . . . ?
O2 N1 C5 C6 -138.74(19) . . . . ?
O3 N1 C5 C6 40.0(2) . . . . ?
O2 N1 C5 C4 42.2(3) . . . . ?
O3 N1 C5 C4 -139.12(19) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
N1 C5 C6 C7 179.92(17) . . . . ?
C5 C6 C7 C8 -1.6(3) . . . . ?
C5 C6 C7 C10 178.16(17) . . . . ?
C6 C7 C8 C9 2.4(3) . . . . ?
C10 C7 C8 C9 -177.34(18) . . . . ?
C7 C8 C9 C4 -0.6(3) . . . . ?
O1 C4 C9 C8 176.08(18) . . . . ?
C5 C4 C9 C8 -1.9(3) . . . . ?
C11 N2 C10 C7 -179.38(17) . . . . ?
Cu1 N2 C10 C7 16.8(3) . . . . ?
C6 C7 C10 N2 -153.31(19) . . . . ?
C8 C7 C10 N2 26.4(3) . . . . ?
C10 N2 C11 C12 -132.36(18) . . . . ?
Cu1 N2 C11 C12 35.72(17) . . . . ?
C13 N3 C12 C11 -128.85(17) . . . . ?
Cu1 N3 C12 C11 41.90(17) . . . . ?
N2 C11 C12 N3 -53.5(2) . . . . ?
C12 N3 C13 C14 179.85(18) . . . . ?
Cu1 N3 C13 C14 13.3(3) . . . . ?
N3 C13 C14 C15 14.5(3) . . . . ?
N3 C13 C14 C19 -165.53(19) . . . . ?
C19 C14 C15 C16 0.3(3) . . . . ?
C13 C14 C15 C16 -179.67(18) . . . . ?
C14 C15 C16 C17 -1.4(3) . . . . ?
C14 C15 C16 N4 178.06(17) . . . . ?
O5 N4 C16 C15 164.17(17) . . . . ?
O4 N4 C16 C15 -15.6(3) . . . . ?
O5 N4 C16 C17 -16.4(3) . . . . ?
O4 N4 C16 C17 163.88(18) . . . . ?
C20 O6 C17 C18 -0.8(3) . . . . ?
C20 O6 C17 C16 179.0(2) . . . . ?
C15 C16 C17 O6 -178.27(19) . . . . ?
N4 C16 C17 O6 2.3(3) . . . . ?
C15 C16 C17 C18 1.5(3) . . . . ?
N4 C16 C17 C18 -177.90(19) . . . . ?
O6 C17 C18 C19 179.1(2) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 C14 -0.3(4) . . . . ?
C15 C14 C19 C18 0.5(3) . . . . ?
C13 C14 C19 C18 -179.5(2) . . . . ?
C17 O6 C20 C21 -174.74(19) . . . . ?
O6 C20 C21 C22 2.7(3) . . . . ?
C26 O7 C25 C24B -174.1(4) . . . . ?
C26 O7 C25 C24A -176.6(6) . . . . ?
C23B C24B C25 O7 -11.0(9) . . . . ?
C23A C24A C25 O7 126.9(8) . . . . ?
C25 O7 C26 C31 -7.5(3) . . . . ?
C25 O7 C26 C27 171.9(2) . . . . ?
O7 C26 C27 C28 -179.7(2) . . . . ?
C31 C26 C27 C28 -0.3(3) . . . . ?
O7 C26 C27 N5A -8.7(4) . . . . ?
C31 C26 C27 N5A 170.8(3) . . . . ?
O7 C26 C27 N5B 10.2(4) . . . . ?
C31 C26 C27 N5B -170.4(4) . . . . ?
O9A N5A C27 C28 -131.2(6) . . . . ?
O8A N5A C27 C28 51.7(8) . . . . ?
O9A N5A C27 C26 57.4(8) . . . . ?
O8A N5A C27 C26 -119.7(6) . . . . ?
O8B N5B C27 C28 112.4(10) . . . . ?
O9B N5B C27 C28 -61.0(13) . . . . ?
O8B N5B C27 C26 -77.1(11) . . . . ?
O9B N5B C27 C26 109.6(11) . . . . ?
C26 C27 C28 C29 1.1(4) . . . . ?
N5A C27 C28 C29 -169.9(3) . . . . ?
N5B C27 C28 C29 171.3(4) . . . . ?
C27 C28 C29 C30 -1.2(3) . . . . ?
C27 C28 C29 C32 175.6(2) . . . . ?
C28 C29 C30 C31 0.5(3) . . . . ?
C32 C29 C30 C31 -176.15(18) . . . . ?
C29 C30 C31 C26 0.4(3) . . . . ?
O7 C26 C31 C30 178.93(19) . . . . ?
C27 C26 C31 C30 -0.5(3) . . . . ?
C33 N6 C32 C29 175.19(17) . . . . ?
Cu1 N6 C32 C29 13.7(3) . . . . ?
C28 C29 C32 N6 -155.6(2) . . . . ?
C30 C29 C32 N6 21.0(3) . . . . ?
C32 N6 C33 C34 -127.92(17) . . . . ?
Cu1 N6 C33 C34 38.92(16) . . . . ?
C35 N7 C34 C33 -125.85(17) . . . . ?
Cu1 N7 C34 C33 44.01(16) . . . . ?
N6 C33 C34 N7 -57.59(19) . . . . ?
C34 N7 C35 C36 177.23(17) . . . . ?
Cu1 N7 C35 C36 12.2(3) . . . . ?
N7 C35 C36 C37 19.4(3) . . . . ?
N7 C35 C36 C41 -158.81(19) . . . . ?
C41 C36 C37 C38 4.2(3) . . . . ?
C35 C36 C37 C38 -173.94(19) . . . . ?
C36 C37 C38 C39 -2.5(3) . . . . ?
C36 C37 C38 N8 174.73(18) . . . . ?
O10 N8 C38 C37 34.5(3) . . . . ?
O11 N8 C38 C37 -142.3(2) . . . . ?
O10 N8 C38 C39 -148.2(2) . . . . ?
O11 N8 C38 C39 35.0(3) . . . . ?
C42 O12 C39 C40 0.6(3) . . . . ?
C42 O12 C39 C38 178.65(19) . . . . ?
C37 C38 C39 O12 -179.47(19) . . . . ?
N8 C38 C39 O12 3.4(3) . . . . ?
C37 C38 C39 C40 -1.3(3) . . . . ?
N8 C38 C39 C40 -178.41(19) . . . . ?
O12 C39 C40 C41 -178.7(2) . . . . ?
C38 C39 C40 C41 3.3(3) . . . . ?
C39 C40 C41 C36 -1.6(3) . . . . ?
C37 C36 C41 C40 -2.3(3) . . . . ?
C35 C36 C41 C40 176.00(18) . . . . ?
C39 O12 C42 C43B 178.2(3) . . . . ?
C39 O12 C42 C43A 163.3(4) . . . . ?
C44B C43B C42 O12 -128.7(5) . . . . ?
C44A C43A C42 O12 125.7(8) . . . . ?
O14 N9 C45 C46 -19.4(3) . . . . ?
O13 N9 C45 C46 160.1(2) . . . . ?
O14 N9 C45 C50 162.5(3) . . . . ?
O13 N9 C45 C50 -18.0(3) . . . . ?
C50 C45 C46 C47 -0.2(4) . . . . ?
N9 C45 C46 C47 -178.3(2) . . . . ?
C45 C46 C47 C48 -1.0(4) . . . . ?
C46 C47 C48 C49 0.7(4) . . . . ?
C47 C48 C49 C50 0.8(4) . . . . ?
C46 C45 C50 C49 1.6(3) . . . . ?
N9 C45 C50 C49 179.7(2) . . . . ?
C48 C49 C50 C45 -1.9(4) . . . . ?

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.051

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether, nitrobenzene'
