# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_lp441
_database_code_depnum_ccdc_archive 'CCDC 1011858'
_audit_update_record             
;
2015-02-20 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C79 H74 Cu3 F12 N12 O5 P2'
_chemical_formula_weight         1752.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c :H'
_space_group_name_Hall           '-R 3 2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   13.8259(10)
_cell_length_b                   13.8259(10)
_cell_length_c                   68.225(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     11294(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3665
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      19.8

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             5382
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.974
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   '30 W microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker Apex II Quasar'
_diffrn_measurement_method       'ω & π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26387
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -82
_diffrn_reflns_limit_l_max       84
_diffrn_reflns_theta_min         2.078
_diffrn_reflns_theta_max         25.985
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2447
_reflns_number_gt                1476
_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       Apex2
_computing_cell_refinement       Apex2
_computing_data_reduction        Apex2
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    dimond3
_computing_publication_material  WinGX

_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)+(0.0620P)²+27.4471P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   'F map'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2447
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.091
_refine_ls_R_factor_gt           0.044
_refine_ls_wR_factor_ref         0.141
_refine_ls_wR_factor_gt          0.110
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.46724(4) 0.3333 0.0833 0.0460(3) Uani 1 2 d S T P A .
O1 O 0.5613(4) 0.2632(4) 0.08342(9) 0.0407(13) Uani 0.5 1 d . . P . .
N1 N 0.4630(3) 0.3266(3) 0.05391(6) 0.0544(9) Uani 1 1 d . . . . .
N2 N 0.4148(3) 0.4514(3) 0.07722(7) 0.0603(10) Uani 1 1 d . . . . .
C C 0.6667 0.3333 0.0833 0.036(2) Uani 1 6 d S T P . .
C1 C 0.4898(3) 0.2658(4) 0.04243(7) 0.0630(13) Uani 1 1 d . . . A 1
H1 H 0.5090 0.2158 0.0485 0.076 Uiso 1 1 calc R U . A 1
C2 C 0.4912(4) 0.2716(5) 0.02228(8) 0.0783(15) Uani 1 1 d . . . A 1
H2 H 0.5122 0.2273 0.0147 0.094 Uiso 1 1 calc R U . A 1
C3 C 0.4626(4) 0.3408(6) 0.01342(9) 0.0884(18) Uani 1 1 d . . . A 1
H3 H 0.4640 0.3465 -0.0005 0.106 Uiso 1 1 calc R U . A 1
C4 C 0.4311(4) 0.4038(5) 0.02485(9) 0.0845(17) Uani 1 1 d . . . A 1
H4 H 0.4086 0.4515 0.0189 0.101 Uiso 1 1 calc R U . A 1
C5 C 0.4333(4) 0.3955(4) 0.04521(8) 0.0635(13) Uani 1 1 d . . . A 1
C6 C 0.4019(4) 0.4578(4) 0.05883(9) 0.0701(15) Uani 1 1 d . . . A 1
H6 H 0.3725 0.5022 0.0540 0.084 Uiso 1 1 calc R U . A 1
C7 C 0.3728(4) 0.5042(4) 0.09096(10) 0.0797(16) Uani 1 1 d . . . B 1
H7A H 0.3013 0.4452 0.0965 0.096 Uiso 1 1 calc R U . B 1
H7B H 0.3565 0.5556 0.0834 0.096 Uiso 1 1 calc R U . B 1
C8 C 0.4478(14) 0.5674(19) 0.1074(3) 0.086(11) Uani 0.5 1 d G . P B 1
C9 C 0.3996(10) 0.5529(18) 0.1258(3) 0.088(6) Uani 0.5 1 d G . P B 1
H9 H 0.3218 0.5034 0.1275 0.106 Uiso 0.5 1 calc R U P B 1
C10 C 0.4653(13) 0.6109(18) 0.1418(2) 0.116(7) Uani 0.5 1 d G . P B 1
H10 H 0.4324 0.6010 0.1544 0.139 Uiso 0.5 1 calc R U P B 1
C11 C 0.5792(12) 0.6834(16) 0.13939(18) 0.124(10) Uani 0.5 1 d G . P B 1
H11 H 0.6241 0.7230 0.1503 0.149 Uiso 0.5 1 calc R U P B 1
C12 C 0.6273(10) 0.6979(17) 0.1210(2) 0.092(6) Uani 0.5 1 d G . P B 1
H12 H 0.7052 0.7474 0.1193 0.111 Uiso 0.5 1 calc R U P B 1
C13 C 0.5616(15) 0.640(2) 0.10494(18) 0.081(5) Uani 0.5 1 d G . P B 1
H13 H 0.5946 0.6498 0.0923 0.097 Uiso 0.5 1 calc R U P B 1
C8' C 0.4597(14) 0.5752(18) 0.1055(3) 0.067(8) Uani 0.5 1 d G . P C 2
C9' C 0.4385(11) 0.5731(18) 0.1254(3) 0.105(8) Uani 0.5 1 d G . P C 2
H9' H 0.3669 0.5214 0.1305 0.126 Uiso 0.5 1 calc R U P C 2
C10' C 0.5222(14) 0.6466(17) 0.1380(2) 0.139(11) Uani 0.5 1 d G . P C 2
H10' H 0.5077 0.6451 0.1517 0.166 Uiso 0.5 1 calc R U P C 2
C11' C 0.6270(12) 0.7222(14) 0.13064(18) 0.098(7) Uani 0.5 1 d G . P C 2
H11' H 0.6842 0.7725 0.1392 0.118 Uiso 0.5 1 calc R U P C 2
C12' C 0.6482(11) 0.7244(17) 0.11068(19) 0.102(6) Uani 0.5 1 d G . P C 2
H12' H 0.7198 0.7761 0.1056 0.123 Uiso 0.5 1 calc R U P C 2
C13' C 0.5645(16) 0.651(2) 0.09810(17) 0.095(7) Uani 0.5 1 d G . P C 2
H13' H 0.5789 0.6523 0.0845 0.114 Uiso 0.5 1 calc R U P C 2
P1 P 0.3333 0.6667 0.03212(3) 0.0544(5) Uani 1 3 d S T P . .
F1 F 0.24592(19) 0.5593(2) 0.04649(4) 0.0713(8) Uani 1 1 d . . . . .
F2 F 0.4226(2) 0.7747(2) 0.01838(5) 0.0839(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.973(4) . ?
Cu1 O1 1.973(4) 17_554 ?
Cu1 N1 2.009(4) 17_554 ?
Cu1 N1 2.009(4) . ?
Cu1 N2 2.132(3) 17_554 ?
Cu1 N2 2.132(3) . ?
O1 O1 0.845(8) 16_544 ?
O1 C 1.285(4) . ?
O1 O1 1.679(9) 17_554 ?
N1 C1 1.330(6) . ?
N1 C5 1.349(5) . ?
N2 C6 1.276(6) . ?
N2 C7 1.475(6) . ?
C O1 1.284(4) 17_554 ?
C O1 1.285(4) 2_655 ?
C O1 1.285(4) 16_544 ?
C O1 1.285(4) 3_665 ?
C O1 1.285(4) 18_654 ?
C1 C2 1.377(6) . ?
C2 C3 1.347(8) . ?
C3 C4 1.391(8) . ?
C4 C5 1.396(7) . ?
C5 C6 1.472(7) . ?
C7 C8 1.479(13) . ?
C8 C9 1.3900 . ?
C8 C13 1.3900 . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C11 C12 1.3900 . ?
C12 C13 1.3900 . ?
C8' C9' 1.3900 . ?
C8' C13' 1.3900 . ?
C9' C10' 1.3900 . ?
C10' C11' 1.3900 . ?
C11' C12' 1.3900 . ?
C12' C13' 1.3900 . ?
P1 F2 1.670(3) . ?
P1 F2 1.670(3) 2_665 ?
P1 F2 1.670(3) 3_565 ?
P1 F1 1.682(3) 3_565 ?
P1 F1 1.682(3) 2_665 ?
P1 F1 1.682(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
O1 Cu1 O1 50.4(3) . 17_554 ?
O1 Cu1 N1 91.1(2) . 17_554 ?
O1 Cu1 N1 89.5(2) 17_554 17_554 ?
O1 Cu1 N1 89.5(2) . . ?
O1 Cu1 N1 91.1(2) 17_554 . ?
N1 Cu1 N1 179.33(19) 17_554 . ?
O1 Cu1 N2 111.80(15) . 17_554 ?
O1 Cu1 N2 159.51(18) 17_554 17_554 ?
N1 Cu1 N2 80.02(16) 17_554 17_554 ?
N1 Cu1 N2 99.48(15) . 17_554 ?
O1 Cu1 N2 159.51(18) . . ?
O1 Cu1 N2 111.80(15) 17_554 . ?
N1 Cu1 N2 99.49(15) 17_554 . ?
N1 Cu1 N2 80.02(16) . . ?
N2 Cu1 N2 87.43(18) 17_554 . ?
O1 O1 C 70.81(19) 16_544 . ?
O1 O1 O1 119.99(3) 16_544 17_554 ?
C O1 O1 49.19(18) . 17_554 ?
O1 O1 Cu1 175.1(4) 16_544 . ?
C O1 Cu1 114.0(3) . . ?
O1 O1 Cu1 64.81(13) 17_554 . ?
C1 N1 C5 117.8(4) . . ?
C1 N1 Cu1 127.4(3) . . ?
C5 N1 Cu1 114.8(3) . . ?
C6 N2 C7 119.1(4) . . ?
C6 N2 Cu1 111.0(3) . . ?
C7 N2 Cu1 128.6(4) . . ?
O1 C O1 81.6(4) 17_554 . ?
O1 C O1 158.4(4) 17_554 2_655 ?
O1 C O1 119.999(6) . 2_655 ?
O1 C O1 120.004(6) 17_554 16_544 ?
O1 C O1 38.4(4) . 16_544 ?
O1 C O1 81.6(4) 2_655 16_544 ?
O1 C O1 38.4(4) 17_554 3_665 ?
O1 C O1 119.997(6) . 3_665 ?
O1 C O1 119.998(7) 2_655 3_665 ?
O1 C O1 158.4(4) 16_544 3_665 ?
O1 C O1 120.001(7) 17_554 18_654 ?
O1 C O1 158.4(4) . 18_654 ?
O1 C O1 38.4(4) 2_655 18_654 ?
O1 C O1 119.989(7) 16_544 18_654 ?
O1 C O1 81.6(4) 3_665 18_654 ?
N1 C1 C2 123.5(5) . . ?
C3 C2 C1 119.2(6) . . ?
C2 C3 C4 119.2(5) . . ?
C3 C4 C5 118.7(5) . . ?
N1 C5 C4 121.5(5) . . ?
N1 C5 C6 114.7(4) . . ?
C4 C5 C6 123.8(5) . . ?
N2 C6 C5 119.2(4) . . ?
N2 C7 C8 116.1(10) . . ?
C9 C8 C13 120.0 . . ?
C9 C8 C7 117.1(14) . . ?
C13 C8 C7 122.9(14) . . ?
C10 C9 C8 120.0 . . ?
C11 C10 C9 120.0 . . ?
C10 C11 C12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C12 C13 C8 120.0 . . ?
C9' C8' C13' 120.0 . . ?
C8' C9' C10' 120.0 . . ?
C11' C10' C9' 120.0 . . ?
C10' C11' C12' 120.0 . . ?
C13' C12' C11' 120.0 . . ?
C12' C13' C8' 120.0 . . ?
F2 P1 F2 91.59(18) . 2_665 ?
F2 P1 F2 91.59(18) . 3_565 ?
F2 P1 F2 91.59(18) 2_665 3_565 ?
F2 P1 F1 89.87(14) . 3_565 ?
F2 P1 F1 89.06(14) 2_665 3_565 ?
F2 P1 F1 178.39(18) 3_565 3_565 ?
F2 P1 F1 89.06(14) . 2_665 ?
F2 P1 F1 178.39(18) 2_665 2_665 ?
F2 P1 F1 89.87(14) 3_565 2_665 ?
F1 P1 F1 89.46(16) 3_565 2_665 ?
F2 P1 F1 178.38(19) . . ?
F2 P1 F1 89.87(14) 2_665 . ?
F2 P1 F1 89.07(14) 3_565 . ?
F1 P1 F1 89.46(16) 3_565 . ?
F1 P1 F1 89.46(16) 2_665 . ?

_refine_diff_density_max         0.36
_refine_diff_density_min         -0.37
_refine_diff_density_rms         0.06

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_lp644b
_database_code_depnum_ccdc_archive 'CCDC 1011860'
_audit_update_record             
;
2015-02-20 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H41 B2 Cu F8 N7'
_chemical_formula_weight         905.00

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   11.5185(8)
_cell_length_b                   18.7898(14)
_cell_length_c                   19.2943(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4175.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9873
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      26.0

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             1860
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.601
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   '30 W microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker Apex II Quasar'
_diffrn_measurement_method       'ω & π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31700
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.059
_diffrn_reflns_theta_max         25.988
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             8009
_reflns_number_gt                7389
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_max     0.953
_reflns_Friedel_fraction_full    0.964

_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       Apex2
_computing_cell_refinement       Apex2
_computing_data_reduction        Apex2
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    Dimond3
_computing_publication_material  WinGX

_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)+(0.0473P)²+1.0352P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   'F map'
_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 x determined using 3033 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.002(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8009
_refine_ls_number_parameters     560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.038
_refine_ls_R_factor_gt           0.033
_refine_ls_wR_factor_ref         0.086
_refine_ls_wR_factor_gt          0.084
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
C1 C 0.9954(4) 0.53959(19) 0.1043(2) 0.0335(9) Uani 1 1 d . . . . .
H1 H 1.0060 0.5048 0.1394 0.040 Uiso 1 1 calc R U . . .
C2 C 1.0605(4) 0.5361(2) 0.0442(2) 0.0414(10) Uani 1 1 d . . . . .
H2 H 1.1139 0.4982 0.0375 0.050 Uiso 1 1 calc R U . . .
C3 C 1.0477(4) 0.5879(2) -0.0063(2) 0.0398(10) Uani 1 1 d . . . . .
H3 H 1.0941 0.5863 -0.0469 0.048 Uiso 1 1 calc R U . . .
C4 C 0.9680(4) 0.6415(2) 0.0024(2) 0.0388(10) Uani 1 1 d . . . . .
H4 H 0.9584 0.6765 -0.0326 0.047 Uiso 1 1 calc R U . . .
C5 C 0.9014(3) 0.6447(2) 0.06236(19) 0.0325(8) Uani 1 1 d . . . . .
H5 H 0.8466 0.6820 0.0683 0.039 Uiso 1 1 calc R U . . .
C6 C 0.9149(3) 0.59340(18) 0.11374(18) 0.0273(8) Uani 1 1 d . . . . .
C7 C 0.8457(3) 0.59842(18) 0.1801(2) 0.0305(7) Uani 1 1 d . . . . .
H7A H 0.8945 0.5823 0.2194 0.037 Uiso 1 1 calc R U . . .
H7B H 0.8243 0.6487 0.1885 0.037 Uiso 1 1 calc R U . . .
C8 C 0.6428(3) 0.58710(15) 0.17982(18) 0.0250(7) Uani 1 1 d . . . . .
H8 H 0.6405 0.6376 0.1821 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5350(3) 0.54624(15) 0.17919(17) 0.0232(7) Uani 1 1 d . . . . .
C10 C 0.4266(3) 0.57809(18) 0.17285(18) 0.0319(8) Uani 1 1 d . . . . .
H10 H 0.4199 0.6284 0.1694 0.038 Uiso 1 1 calc R U . . .
C11 C 0.3282(3) 0.5352(2) 0.1716(2) 0.0381(9) Uani 1 1 d . . . . .
H11 H 0.2536 0.5560 0.1664 0.046 Uiso 1 1 calc R U . . .
C12 C 0.3395(3) 0.4628(2) 0.1781(2) 0.0335(8) Uani 1 1 d . . . . .
H12 H 0.2729 0.4329 0.1784 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4507(3) 0.43398(17) 0.18416(16) 0.0235(6) Uani 1 1 d . . . . .
C14 C 0.4728(3) 0.35694(17) 0.18982(17) 0.0262(7) Uani 1 1 d . . . . .
H14 H 0.4104 0.3241 0.1932 0.031 Uiso 1 1 calc R U . . .
C15 C 0.6001(4) 0.25916(17) 0.1944(2) 0.0327(9) Uani 1 1 d . . . . .
H15A H 0.6318 0.2423 0.1496 0.039 Uiso 1 1 calc R U . . .
H15B H 0.5268 0.2333 0.2034 0.039 Uiso 1 1 calc R U . . .
C16 C 0.6857(4) 0.24372(15) 0.25139(19) 0.0297(8) Uani 1 1 d . . . . .
C17 C 0.6555(3) 0.25823(16) 0.3199(2) 0.0325(8) Uani 1 1 d . . . . .
H17 H 0.5819 0.2784 0.3303 0.039 Uiso 1 1 calc R U . . .
C18 C 0.7329(4) 0.24332(19) 0.3730(2) 0.0425(11) Uani 1 1 d . . . . .
H18 H 0.7121 0.2528 0.4198 0.051 Uiso 1 1 calc R U . . .
C19 C 0.8398(4) 0.2148(2) 0.3579(3) 0.0513(12) Uani 1 1 d . . . . .
H19 H 0.8928 0.2047 0.3944 0.062 Uiso 1 1 calc R U . . .
C20 C 0.8708(4) 0.2008(2) 0.2905(3) 0.0528(12) Uani 1 1 d . . . . .
H20 H 0.9450 0.1813 0.2805 0.063 Uiso 1 1 calc R U . . .
C21 C 0.7934(4) 0.21511(18) 0.2366(2) 0.0408(9) Uani 1 1 d . . . . .
H21 H 0.8147 0.2053 0.1901 0.049 Uiso 1 1 calc R U . . .
C22 C 0.4490(4) 0.5042(2) 0.0009(2) 0.0380(9) Uani 1 1 d . . . . .
H22 H 0.3946 0.4663 0.0023 0.046 Uiso 1 1 calc R U . . .
C23 C 0.4110(4) 0.5729(2) -0.0124(2) 0.0463(10) Uani 1 1 d . . . . .
H23 H 0.3310 0.5813 -0.0212 0.056 Uiso 1 1 calc R U . . .
C24 C 0.4871(4) 0.6287(2) -0.0131(2) 0.0418(10) Uani 1 1 d . . . . .
H24 H 0.4603 0.6757 -0.0216 0.050 Uiso 1 1 calc R U . . .
C25 C 0.6053(4) 0.6158(2) -0.0012(2) 0.0349(9) Uani 1 1 d . . . . .
H25 H 0.6592 0.6541 -0.0013 0.042 Uiso 1 1 calc R U . . .
C26 C 0.6434(4) 0.54674(18) 0.01081(18) 0.0302(8) Uani 1 1 d . . . . .
H26 H 0.7237 0.5380 0.0182 0.036 Uiso 1 1 calc R U . . .
C27 C 0.5655(3) 0.49044(18) 0.01209(16) 0.0264(7) Uani 1 1 d . . . . .
C28 C 0.6056(3) 0.41470(18) 0.02317(17) 0.0273(8) Uani 1 1 d . . . . .
H28A H 0.5396 0.3861 0.0407 0.033 Uiso 1 1 calc R U . . .
H28B H 0.6295 0.3943 -0.0219 0.033 Uiso 1 1 calc R U . . .
C29 C 0.7954(3) 0.37920(17) 0.05252(17) 0.0288(7) Uani 1 1 d . . . . .
H29 H 0.8060 0.3652 0.0056 0.035 Uiso 1 1 calc R U . . .
C30 C 0.8865(3) 0.36700(17) 0.1049(2) 0.0284(8) Uani 1 1 d . . . . .
C31 C 0.9949(4) 0.3362(2) 0.0941(2) 0.0402(10) Uani 1 1 d . . . . .
H31 H 1.0192 0.3217 0.0492 0.048 Uiso 1 1 calc R U . . .
C32 C 1.0665(4) 0.3276(2) 0.1516(3) 0.0453(11) Uani 1 1 d . . . . .
H32 H 1.1417 0.3076 0.1458 0.054 Uiso 1 1 calc R U . . .
C33 C 1.0304(3) 0.34737(18) 0.2167(2) 0.0365(9) Uani 1 1 d . . . . .
H33 H 1.0793 0.3411 0.2559 0.044 Uiso 1 1 calc R U . . .
C34 C 0.9202(3) 0.37685(17) 0.22363(19) 0.0283(8) Uani 1 1 d . . . . .
C35 C 0.8620(3) 0.39725(17) 0.28860(19) 0.0282(8) Uani 1 1 d . . . . .
H35 H 0.8993 0.3921 0.3322 0.034 Uiso 1 1 calc R U . . .
C36 C 0.6941(4) 0.43754(16) 0.34624(17) 0.0300(7) Uani 1 1 d . . . . .
H36A H 0.7363 0.4184 0.3869 0.036 Uiso 1 1 calc R U . . .
H36B H 0.6177 0.4136 0.3438 0.036 Uiso 1 1 calc R U . . .
C37 C 0.6761(3) 0.51704(17) 0.35553(17) 0.0262(8) Uani 1 1 d . . . . .
C38 C 0.7687(3) 0.56392(18) 0.34897(16) 0.0302(8) Uani 1 1 d . . . . .
H38 H 0.8440 0.5465 0.3382 0.036 Uiso 1 1 calc R U . . .
C39 C 0.7507(4) 0.63641(18) 0.35822(19) 0.0375(10) Uani 1 1 d . . . . .
H39 H 0.8138 0.6686 0.3532 0.045 Uiso 1 1 calc R U . . .
C40 C 0.6419(4) 0.6619(2) 0.3746(2) 0.0412(10) Uani 1 1 d . . . . .
H40 H 0.6304 0.7115 0.3807 0.049 Uiso 1 1 calc R U . . .
C41 C 0.5495(4) 0.6156(2) 0.3822(2) 0.0399(10) Uani 1 1 d . . . . .
H41 H 0.4748 0.6330 0.3942 0.048 Uiso 1 1 calc R U . . .
C42 C 0.5676(4) 0.54340(19) 0.37190(19) 0.0340(9) Uani 1 1 d . . . . .
H42 H 0.5041 0.5115 0.3762 0.041 Uiso 1 1 calc R U . . .
B2 B 0.6956(5) 0.8056(2) 0.1599(2) 0.0360(10) Uani 1 1 d . . . . .
N1 N 0.7397(2) 0.55487(12) 0.17729(15) 0.0234(6) Uani 1 1 d . . . . .
N2 N 0.5459(2) 0.47512(13) 0.18428(14) 0.0203(5) Uani 1 1 d . . . . .
N3 N 0.5766(3) 0.33582(14) 0.19013(14) 0.0249(6) Uani 1 1 d . . . . .
N4 N 0.7030(3) 0.40884(13) 0.07225(13) 0.0238(6) Uani 1 1 d . . . . .
N5 N 0.8531(2) 0.38683(13) 0.16820(15) 0.0242(6) Uani 1 1 d . . . . .
N6 N 0.7596(3) 0.42203(13) 0.28370(14) 0.0236(6) Uani 1 1 d . . . . .
F1 F 0.7172(3) 0.77235(15) 0.22350(14) 0.0708(9) Uani 1 1 d . . . . .
F2 F 0.6463(4) 0.75797(17) 0.1173(2) 0.1126(16) Uani 1 1 d . . . . .
F3 F 0.7953(3) 0.8301(2) 0.1352(2) 0.1141(14) Uani 1 1 d . . . . .
F4 F 0.6186(3) 0.86200(13) 0.16878(14) 0.0645(8) Uani 1 1 d . . . . .
Cu1 Cu 0.70161(3) 0.42996(2) 0.17960(2) 0.01915(10) Uani 1 1 d . . . . .
B3 B 0.7721(4) 0.1801(2) 0.0031(2) 0.0362(11) Uani 1 1 d . . . . .
F5 F 0.7003(3) 0.23817(14) -0.0010(2) 0.0783(9) Uani 1 1 d . . . . .
F6 F 0.7055(3) 0.11961(14) 0.01123(17) 0.0715(8) Uani 1 1 d . . . . .
F7 F 0.8481(4) 0.1838(3) 0.05738(19) 0.1058(14) Uani 1 1 d . . . . .
F8 F 0.8312(3) 0.17352(16) -0.05738(15) 0.0775(10) Uani 1 1 d . . . . .
C43 C 0.8619(4) 0.02022(19) 0.1833(2) 0.0369(8) Uani 1 1 d . . . . .
C44 C 0.7494(4) 0.0260(2) 0.1497(2) 0.0434(10) Uani 1 1 d . . . . .
H44A H 0.7149 -0.0214 0.1452 0.065 Uiso 1 1 calc R U . . .
H44B H 0.7591 0.0471 0.1036 0.065 Uiso 1 1 calc R U . . .
H44C H 0.6984 0.0563 0.1777 0.065 Uiso 1 1 calc R U . . .
N7 N 0.9479(4) 0.0145(2) 0.2108(2) 0.0553(10) 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
C1 C2 1.383(6) . ?
C1 C6 1.384(5) . ?
C2 C3 1.384(6) . ?
C3 C4 1.374(6) . ?
C4 C5 1.389(5) . ?
C5 C6 1.391(5) . ?
C6 C7 1.511(5) . ?
C7 N1 1.471(4) . ?
C8 N1 1.271(4) . ?
C8 C9 1.460(5) . ?
C9 N2 1.346(4) . ?
C9 C10 1.390(5) . ?
C10 C11 1.390(5) . ?
C11 C12 1.373(5) . ?
C12 C13 1.396(5) . ?
C13 N2 1.341(4) . ?
C13 C14 1.474(5) . ?
C14 N3 1.260(5) . ?
C15 N3 1.468(4) . ?
C15 C16 1.505(5) . ?
C16 C21 1.382(6) . ?
C16 C17 1.395(6) . ?
C17 C18 1.387(6) . ?
C18 C19 1.374(7) . ?
C19 C20 1.375(7) . ?
C20 C21 1.395(6) . ?
C22 C27 1.383(5) . ?
C22 C23 1.388(6) . ?
C23 C24 1.367(6) . ?
C24 C25 1.402(6) . ?
C25 C26 1.388(5) . ?
C26 C27 1.387(5) . ?
C27 C28 1.511(5) . ?
C28 N4 1.472(4) . ?
C29 N4 1.261(5) . ?
C29 C30 1.475(5) . ?
C30 N5 1.334(5) . ?
C30 C31 1.392(5) . ?
C31 C32 1.393(6) . ?
C32 C33 1.374(6) . ?
C33 C34 1.392(5) . ?
C34 N5 1.332(5) . ?
C34 C35 1.473(5) . ?
C35 N6 1.272(5) . ?
C36 N6 1.452(4) . ?
C36 C37 1.519(4) . ?
C37 C42 1.381(5) . ?
C37 C38 1.390(5) . ?
C38 C39 1.389(5) . ?
C39 C40 1.378(6) . ?
C40 C41 1.382(6) . ?
C41 C42 1.387(5) . ?
B2 F3 1.326(6) . ?
B2 F2 1.340(5) . ?
B2 F4 1.393(5) . ?
B2 F1 1.399(5) . ?
N1 Cu1 2.388(2) . ?
N2 Cu1 1.987(3) . ?
N3 Cu1 2.290(3) . ?
N4 Cu1 2.109(3) . ?
N5 Cu1 1.937(3) . ?
N6 Cu1 2.122(3) . ?
B3 F8 1.357(5) . ?
B3 F7 1.367(6) . ?
B3 F5 1.371(5) . ?
B3 F6 1.380(5) . ?
C43 N7 1.128(5) . ?
C43 C44 1.453(6) . ?

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
C2 C1 C6 120.6(4) . . ?
C1 C2 C3 119.9(4) . . ?
C4 C3 C2 120.1(4) . . ?
C3 C4 C5 120.2(4) . . ?
C4 C5 C6 120.1(4) . . ?
C1 C6 C5 119.1(3) . . ?
C1 C6 C7 120.7(3) . . ?
C5 C6 C7 120.1(3) . . ?
N1 C7 C6 111.8(3) . . ?
N1 C8 C9 119.8(3) . . ?
N2 C9 C10 121.2(3) . . ?
N2 C9 C8 116.3(3) . . ?
C10 C9 C8 122.6(3) . . ?
C9 C10 C11 119.0(3) . . ?
C12 C11 C10 119.7(3) . . ?
C11 C12 C13 118.6(3) . . ?
N2 C13 C12 121.8(3) . . ?
N2 C13 C14 115.2(3) . . ?
C12 C13 C14 123.1(3) . . ?
N3 C14 C13 118.3(3) . . ?
N3 C15 C16 110.5(3) . . ?
C21 C16 C17 119.7(4) . . ?
C21 C16 C15 120.8(3) . . ?
C17 C16 C15 119.5(3) . . ?
C18 C17 C16 120.1(4) . . ?
C19 C18 C17 119.9(4) . . ?
C18 C19 C20 120.5(4) . . ?
C19 C20 C21 120.1(4) . . ?
C16 C21 C20 119.7(4) . . ?
C27 C22 C23 120.6(4) . . ?
C24 C23 C22 120.8(4) . . ?
C23 C24 C25 119.3(4) . . ?
C26 C25 C24 119.7(4) . . ?
C27 C26 C25 120.7(4) . . ?
C22 C27 C26 118.8(3) . . ?
C22 C27 C28 119.6(3) . . ?
C26 C27 C28 121.5(3) . . ?
N4 C28 C27 113.2(3) . . ?
N4 C29 C30 117.6(3) . . ?
N5 C30 C31 120.8(4) . . ?
N5 C30 C29 112.3(3) . . ?
C31 C30 C29 126.9(4) . . ?
C30 C31 C32 117.4(4) . . ?
C33 C32 C31 121.2(4) . . ?
C32 C33 C34 118.1(4) . . ?
N5 C34 C33 120.5(4) . . ?
N5 C34 C35 112.5(3) . . ?
C33 C34 C35 126.9(4) . . ?
N6 C35 C34 117.0(3) . . ?
N6 C36 C37 111.5(3) . . ?
C42 C37 C38 119.2(3) . . ?
C42 C37 C36 120.3(3) . . ?
C38 C37 C36 120.5(3) . . ?
C39 C38 C37 119.7(4) . . ?
C40 C39 C38 120.4(4) . . ?
C39 C40 C41 120.4(3) . . ?
C40 C41 C42 119.0(4) . . ?
C37 C42 C41 121.3(4) . . ?
F3 B2 F2 112.2(5) . . ?
F3 B2 F4 109.3(4) . . ?
F2 B2 F4 108.3(4) . . ?
F3 B2 F1 108.5(4) . . ?
F2 B2 F1 108.4(4) . . ?
F4 B2 F1 110.1(3) . . ?
C8 N1 C7 117.6(3) . . ?
C8 N1 Cu1 107.8(2) . . ?
C7 N1 Cu1 134.3(2) . . ?
C13 N2 C9 119.8(3) . . ?
C13 N2 Cu1 119.4(2) . . ?
C9 N2 Cu1 120.3(2) . . ?
C14 N3 C15 119.0(3) . . ?
C14 N3 Cu1 110.7(2) . . ?
C15 N3 Cu1 130.3(2) . . ?
C29 N4 C28 118.8(3) . . ?
C29 N4 Cu1 112.7(2) . . ?
C28 N4 Cu1 127.7(2) . . ?
C34 N5 C30 121.9(3) . . ?
C34 N5 Cu1 119.3(2) . . ?
C30 N5 Cu1 118.7(2) . . ?
C35 N6 C36 119.5(3) . . ?
C35 N6 Cu1 112.8(2) . . ?
C36 N6 Cu1 127.5(2) . . ?
N5 Cu1 N2 176.06(12) . . ?
N5 Cu1 N4 78.63(12) . . ?
N2 Cu1 N4 97.58(11) . . ?
N5 Cu1 N6 78.15(11) . . ?
N2 Cu1 N6 105.73(11) . . ?
N4 Cu1 N6 156.07(11) . . ?
N5 Cu1 N3 104.69(10) . . ?
N2 Cu1 N3 75.99(10) . . ?
N4 Cu1 N3 86.93(10) . . ?
N6 Cu1 N3 93.42(10) . . ?
N5 Cu1 N1 104.08(10) . . ?
N2 Cu1 N1 75.36(10) . . ?
N4 Cu1 N1 99.51(10) . . ?
N6 Cu1 N1 91.65(10) . . ?
N3 Cu1 N1 151.22(10) . . ?
F8 B3 F7 110.0(4) . . ?
F8 B3 F5 108.9(4) . . ?
F7 B3 F5 113.0(4) . . ?
F8 B3 F6 107.5(3) . . ?
F7 B3 F6 108.1(4) . . ?
F5 B3 F6 109.1(4) . . ?
N7 C43 C44 178.0(5) . . ?

_refine_diff_density_max         0.62
_refine_diff_density_min         -0.31
_refine_diff_density_rms         0.05

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_lp664
_database_code_depnum_ccdc_archive 'CCDC 1011861'
_audit_update_record             
;
2015-02-20 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H38 Cu2 N6 2+, 2(B F4 -)'
_chemical_formula_sum            'C42 H38 B2 Cu2 F8 N6'
_chemical_formula_weight         927.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
F F 0.0171 0.0103 '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                   10.9622(5)
_cell_length_b                   11.7396(6)
_cell_length_c                   18.0232(9)
_cell_angle_alpha                72.041(2)
_cell_angle_beta                 80.116(2)
_cell_angle_gamma                62.834(2)
_cell_volume                     1961.73(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      26.0

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.163
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   '30 W microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker Apex II Quasar'
_diffrn_measurement_method       'ω & π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27260
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.021
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7689
_reflns_number_gt                6341
_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       Apex2
_computing_cell_refinement       Apex2
_computing_data_reduction        Apex2
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    dimond3
_computing_publication_material  WinGX

_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)+(0.0368P)²+1.9903P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct methods'
_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         7689
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.63714(3) 0.49528(3) 0.30755(2) 0.02431(10) Uani 1 1 d . . . . .
Cu2 Cu 0.76852(3) 0.63639(3) 0.23681(2) 0.02244(10) Uani 1 1 d . . . . .
N1 N 0.6469(2) 0.5130(2) 0.40689(12) 0.0207(5) Uani 1 1 d . . . . .
N2 N 0.5874(2) 0.7566(2) 0.28894(12) 0.0179(4) Uani 1 1 d . . . . .
N3 N 0.6870(2) 0.7750(2) 0.14122(12) 0.0204(5) Uani 1 1 d . . . . .
N4 N 0.9332(2) 0.5770(2) 0.29527(12) 0.0210(5) Uani 1 1 d . . . . .
N5 N 0.8748(2) 0.4370(2) 0.22545(12) 0.0191(5) Uani 1 1 d . . . . .
N6 N 0.6084(2) 0.4669(2) 0.21568(12) 0.0203(5) Uani 1 1 d . . . . .
C1 C 0.8218(3) 0.2028(3) 0.40922(17) 0.0280(6) Uani 1 1 d . . . . .
H1 H 0.7349 0.2142 0.3977 0.034 Uiso 1 1 calc R U . . .
C2 C 0.9397(3) 0.1046(3) 0.38725(17) 0.0309(7) Uani 1 1 d . . . . .
H2 H 0.9339 0.0490 0.3606 0.037 Uiso 1 1 calc R U . . .
C3 C 1.0664(3) 0.0874(3) 0.40425(17) 0.0320(7) Uani 1 1 d . . . . .
H3 H 1.1478 0.0192 0.3897 0.038 Uiso 1 1 calc R U . . .
C4 C 1.0748(3) 0.1684(3) 0.44200(17) 0.0336(7) Uani 1 1 d . . . . .
H4 H 1.1620 0.1565 0.4533 0.040 Uiso 1 1 calc R U . . .
C5 C 0.9567(3) 0.2675(3) 0.46373(16) 0.0292(6) Uani 1 1 d . . . . .
H5 H 0.9633 0.3236 0.4896 0.035 Uiso 1 1 calc R U . . .
C6 C 0.8282(3) 0.2854(3) 0.44799(15) 0.0237(6) Uani 1 1 d . . . . .
C7 C 0.6990(3) 0.3912(3) 0.47179(16) 0.0278(6) Uani 1 1 d . . . . .
H7A H 0.6281 0.3574 0.4890 0.033 Uiso 1 1 calc R U . . .
H7B H 0.7170 0.4128 0.5165 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6065(2) 0.6242(3) 0.42263(15) 0.0221(6) Uani 1 1 d . . . . .
H8 H 0.6124 0.6231 0.4748 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5518(2) 0.7526(3) 0.36506(15) 0.0205(5) Uani 1 1 d . . . . .
C10 C 0.4665(3) 0.8666(3) 0.38972(17) 0.0253(6) Uani 1 1 d . . . . .
H10 H 0.4449 0.8611 0.4437 0.030 Uiso 1 1 calc R U . . .
C11 C 0.4139(3) 0.9869(3) 0.33538(18) 0.0281(6) Uani 1 1 d . . . . .
H11 H 0.3549 1.0652 0.3513 0.034 Uiso 1 1 calc R U . . .
C12 C 0.4477(3) 0.9927(3) 0.25714(17) 0.0273(6) Uani 1 1 d . . . . .
H12 H 0.4118 1.0747 0.2184 0.033 Uiso 1 1 calc R U . . .
C13 C 0.5355(2) 0.8758(3) 0.23644(15) 0.0206(5) Uani 1 1 d . . . . .
C14 C 0.5839(3) 0.8774(3) 0.15475(16) 0.0246(6) Uani 1 1 d . . . . .
H14 H 0.5394 0.9527 0.1132 0.030 Uiso 1 1 calc R U . . .
C15 C 0.7349(3) 0.7757(3) 0.05934(15) 0.0271(6) Uani 1 1 d . . . . .
H15A H 0.6836 0.8648 0.0247 0.033 Uiso 1 1 calc R U . . .
H15B H 0.7172 0.7109 0.0438 0.033 Uiso 1 1 calc R U . . .
C16 C 0.8866(3) 0.7402(3) 0.05043(14) 0.0217(6) Uani 1 1 d . . . . .
C17 C 0.9831(3) 0.6102(3) 0.05645(15) 0.0263(6) Uani 1 1 d . . . . .
H17 H 0.9530 0.5429 0.0647 0.032 Uiso 1 1 calc R U . . .
C18 C 1.1228(3) 0.5766(3) 0.05066(16) 0.0326(7) Uani 1 1 d . . . . .
H18 H 1.1875 0.4870 0.0550 0.039 Uiso 1 1 calc R U . . .
C19 C 1.1670(3) 0.6737(4) 0.03867(17) 0.0356(7) Uani 1 1 d . . . . .
H19 H 1.2624 0.6513 0.0348 0.043 Uiso 1 1 calc R U . . .
C20 C 1.0718(3) 0.8041(3) 0.03225(18) 0.0377(8) Uani 1 1 d . . . . .
H20 H 1.1022 0.8712 0.0236 0.045 Uiso 1 1 calc R U . . .
C21 C 0.9328(3) 0.8372(3) 0.03831(16) 0.0299(6) Uani 1 1 d . . . . .
H21 H 0.8684 0.9268 0.0342 0.036 Uiso 1 1 calc R U . . .
C22 C 0.8916(3) 0.8600(3) 0.23968(17) 0.0318(7) Uani 1 1 d . . . . .
H22 H 0.9551 0.8124 0.2048 0.038 Uiso 1 1 calc R U . . .
C23 C 0.8146(4) 0.9955(3) 0.2136(2) 0.0431(8) Uani 1 1 d . . . . .
H23 H 0.8243 1.0405 0.1608 0.052 Uiso 1 1 calc R U . . .
C24 C 0.7234(3) 1.0655(3) 0.2644(2) 0.0478(9) Uani 1 1 d . . . . .
H24 H 0.6699 1.1585 0.2464 0.057 Uiso 1 1 calc R U . . .
C25 C 0.7099(3) 1.0011(3) 0.3409(2) 0.0413(8) Uani 1 1 d . . . . .
H25 H 0.6487 1.0496 0.3759 0.050 Uiso 1 1 calc R U . . .
C26 C 0.7857(3) 0.8653(3) 0.36680(18) 0.0294(7) Uani 1 1 d . . . . .
H26 H 0.7754 0.8210 0.4197 0.035 Uiso 1 1 calc R U . . .
C27 C 0.8765(3) 0.7931(3) 0.31653(16) 0.0244(6) Uani 1 1 d . . . . .
C28 C 0.9544(3) 0.6451(3) 0.34462(17) 0.0289(6) Uani 1 1 d . . . . .
H28A H 1.0535 0.6213 0.3444 0.035 Uiso 1 1 calc R U . . .
H28B H 0.9240 0.6146 0.3990 0.035 Uiso 1 1 calc R U . . .
C29 C 1.0304(3) 0.4684(3) 0.28643(16) 0.0241(6) Uani 1 1 d . . . . .
H29 H 1.1164 0.4341 0.3091 0.029 Uiso 1 1 calc R U . . .
C30 C 1.0071(3) 0.3967(3) 0.24039(15) 0.0210(5) Uani 1 1 d . . . . .
C31 C 1.1159(3) 0.2996(3) 0.21080(16) 0.0257(6) Uani 1 1 d . . . . .
H31 H 1.2075 0.2726 0.2233 0.031 Uiso 1 1 calc R U . . .
C32 C 1.0889(3) 0.2429(3) 0.16311(16) 0.0277(6) Uani 1 1 d . . . . .
H32 H 1.1619 0.1783 0.1407 0.033 Uiso 1 1 calc R U . . .
C33 C 0.9539(3) 0.2812(3) 0.14807(15) 0.0240(6) Uani 1 1 d . . . . .
H33 H 0.9330 0.2423 0.1158 0.029 Uiso 1 1 calc R U . . .
C34 C 0.8496(3) 0.3772(3) 0.18088(14) 0.0198(5) Uani 1 1 d . . . . .
C35 C 0.7043(3) 0.4165(3) 0.16807(15) 0.0210(5) Uani 1 1 d . . . . .
H35 H 0.6820 0.4039 0.1234 0.025 Uiso 1 1 calc R U . . .
C36 C 0.4647(3) 0.5045(3) 0.19887(17) 0.0254(6) Uani 1 1 d . . . . .
H36A H 0.4351 0.4362 0.2321 0.031 Uiso 1 1 calc R U . . .
H36B H 0.4593 0.5096 0.1436 0.031 Uiso 1 1 calc R U . . .
C37 C 0.3717(3) 0.6370(3) 0.21491(16) 0.0231(6) Uani 1 1 d . . . . .
C38 C 0.3161(3) 0.6458(3) 0.28935(16) 0.0275(6) Uani 1 1 d . . . . .
H38 H 0.3360 0.5673 0.3308 0.033 Uiso 1 1 calc R U . . .
C39 C 0.2313(3) 0.7689(3) 0.30352(17) 0.0301(6) Uani 1 1 d . . . . .
H39 H 0.1943 0.7741 0.3547 0.036 Uiso 1 1 calc R U . . .
C40 C 0.2007(3) 0.8833(3) 0.24370(17) 0.0299(6) Uani 1 1 d . . . . .
H40 H 0.1419 0.9672 0.2533 0.036 Uiso 1 1 calc R U . . .
C41 C 0.2567(3) 0.8750(3) 0.16932(17) 0.0323(7) Uani 1 1 d . . . . .
H41 H 0.2361 0.9536 0.1279 0.039 Uiso 1 1 calc R U . . .
C42 C 0.3419(3) 0.7534(3) 0.15527(16) 0.0282(6) Uani 1 1 d . . . . .
H42 H 0.3808 0.7489 0.1043 0.034 Uiso 1 1 calc R U . . .
B1 B 0.5026(3) 0.7455(3) -0.05587(18) 0.0273(7) Uani 1 1 d . . . . .
B2 B 0.6336(3) 0.7139(3) 0.59560(18) 0.0233(6) Uani 1 1 d . . . . .
F1 F 0.61003(19) 0.7694(2) -0.09823(12) 0.0582(6) Uani 1 1 d . . . . .
F2 F 0.4337(3) 0.7208(3) -0.10108(14) 0.0711(7) Uani 1 1 d . . . . .
F3 F 0.55335(18) 0.63747(18) 0.00806(10) 0.0403(4) Uani 1 1 d . . . . .
F4 F 0.4130(2) 0.8565(2) -0.03153(11) 0.0589(6) Uani 1 1 d . . . . .
F5 F 0.52353(16) 0.68309(18) 0.59656(10) 0.0346(4) Uani 1 1 d . . . . .
F6 F 0.75174(16) 0.61806(18) 0.56950(10) 0.0382(4) Uani 1 1 d . . . . .
F7 F 0.60766(17) 0.83702(17) 0.54601(10) 0.0361(4) Uani 1 1 d . . . . .
F8 F 0.65223(16) 0.71007(16) 0.67096(9) 0.0281(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N6 1.889(2) . ?
Cu1 N1 1.891(2) . ?
Cu1 Cu2 2.5864(5) . ?
Cu2 N3 1.971(2) . ?
Cu2 N4 1.977(2) . ?
Cu2 N2 2.106(2) . ?
Cu2 N5 2.145(2) . ?
N1 C8 1.279(3) . ?
N1 C7 1.481(3) . ?
N2 C13 1.349(3) . ?
N2 C9 1.353(3) . ?
N3 C14 1.276(3) . ?
N3 C15 1.478(3) . ?
N4 C29 1.269(3) . ?
N4 C28 1.471(3) . ?
N5 C34 1.347(3) . ?
N5 C30 1.352(3) . ?
N6 C35 1.276(3) . ?
N6 C36 1.488(3) . ?
C1 C2 1.379(4) . ?
C1 C6 1.389(4) . ?
C2 C3 1.384(4) . ?
C3 C4 1.370(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.392(4) . ?
C6 C7 1.499(4) . ?
C8 C9 1.460(4) . ?
C9 C10 1.395(4) . ?
C10 C11 1.372(4) . ?
C11 C12 1.384(4) . ?
C12 C13 1.391(4) . ?
C13 C14 1.474(4) . ?
C15 C16 1.511(4) . ?
C16 C17 1.387(4) . ?
C16 C21 1.391(4) . ?
C17 C18 1.389(4) . ?
C18 C19 1.378(4) . ?
C19 C20 1.386(5) . ?
C20 C21 1.383(4) . ?
C22 C23 1.383(5) . ?
C22 C27 1.390(4) . ?
C23 C24 1.383(5) . ?
C24 C25 1.371(5) . ?
C25 C26 1.383(5) . ?
C26 C27 1.387(4) . ?
C27 C28 1.502(4) . ?
C29 C30 1.470(4) . ?
C30 C31 1.386(4) . ?
C31 C32 1.374(4) . ?
C32 C33 1.386(4) . ?
C33 C34 1.389(4) . ?
C34 C35 1.481(3) . ?
C36 C37 1.507(4) . ?
C37 C38 1.389(4) . ?
C37 C42 1.391(4) . ?
C38 C39 1.392(4) . ?
C39 C40 1.378(4) . ?
C40 C41 1.388(4) . ?
C41 C42 1.379(4) . ?
B1 F2 1.369(4) . ?
B1 F4 1.375(4) . ?
B1 F1 1.382(4) . ?
B1 F3 1.386(4) . ?
B2 F7 1.372(4) . ?
B2 F8 1.392(3) . ?
B2 F6 1.397(3) . ?
B2 F5 1.406(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
N6 Cu1 N1 171.39(9) . . ?
N6 Cu1 Cu2 94.78(7) . . ?
N1 Cu1 Cu2 93.67(7) . . ?
N3 Cu2 N4 134.56(9) . . ?
N3 Cu2 N2 82.18(8) . . ?
N4 Cu2 N2 112.54(8) . . ?
N3 Cu2 N5 115.92(8) . . ?
N4 Cu2 N5 81.16(8) . . ?
N2 Cu2 N5 139.70(8) . . ?
N3 Cu2 Cu1 116.18(6) . . ?
N4 Cu2 Cu1 109.26(7) . . ?
N2 Cu2 Cu1 71.79(6) . . ?
N5 Cu2 Cu1 67.91(6) . . ?
C8 N1 C7 117.5(2) . . ?
C8 N1 Cu1 124.25(19) . . ?
C7 N1 Cu1 118.22(17) . . ?
C13 N2 C9 117.5(2) . . ?
C13 N2 Cu2 106.47(15) . . ?
C9 N2 Cu2 130.29(17) . . ?
C14 N3 C15 118.4(2) . . ?
C14 N3 Cu2 113.34(18) . . ?
C15 N3 Cu2 128.17(18) . . ?
C29 N4 C28 118.6(2) . . ?
C29 N4 Cu2 113.93(18) . . ?
C28 N4 Cu2 127.50(17) . . ?
C34 N5 C30 117.6(2) . . ?
C34 N5 Cu2 130.58(17) . . ?
C30 N5 Cu2 105.56(16) . . ?
C35 N6 C36 118.4(2) . . ?
C35 N6 Cu1 124.07(17) . . ?
C36 N6 Cu1 117.50(16) . . ?
C2 C1 C6 121.0(2) . . ?
C1 C2 C3 119.7(3) . . ?
C4 C3 C2 120.2(3) . . ?
C3 C4 C5 120.2(3) . . ?
C4 C5 C6 120.5(3) . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 C7 120.2(2) . . ?
C5 C6 C7 121.3(3) . . ?
N1 C7 C6 111.6(2) . . ?
N1 C8 C9 123.9(2) . . ?
N2 C9 C10 122.2(3) . . ?
N2 C9 C8 118.2(2) . . ?
C10 C9 C8 119.6(2) . . ?
C11 C10 C9 119.4(3) . . ?
C10 C11 C12 119.3(3) . . ?
C11 C12 C13 118.5(3) . . ?
N2 C13 C12 123.1(2) . . ?
N2 C13 C14 115.9(2) . . ?
C12 C13 C14 120.9(3) . . ?
N3 C14 C13 118.3(3) . . ?
N3 C15 C16 110.1(2) . . ?
C17 C16 C21 118.5(3) . . ?
C17 C16 C15 121.0(2) . . ?
C21 C16 C15 120.5(3) . . ?
C16 C17 C18 121.2(3) . . ?
C19 C18 C17 119.7(3) . . ?
C18 C19 C20 119.7(3) . . ?
C21 C20 C19 120.5(3) . . ?
C20 C21 C16 120.5(3) . . ?
C23 C22 C27 120.4(3) . . ?
C24 C23 C22 120.0(3) . . ?
C25 C24 C23 120.1(3) . . ?
C24 C25 C26 119.9(3) . . ?
C25 C26 C27 120.8(3) . . ?
C26 C27 C22 118.7(3) . . ?
C26 C27 C28 120.3(3) . . ?
C22 C27 C28 121.0(3) . . ?
N4 C28 C27 111.6(2) . . ?
N4 C29 C30 118.7(2) . . ?
N5 C30 C31 122.9(2) . . ?
N5 C30 C29 115.8(2) . . ?
C31 C30 C29 121.3(2) . . ?
C32 C31 C30 118.9(2) . . ?
C31 C32 C33 119.2(2) . . ?
C32 C33 C34 118.9(2) . . ?
N5 C34 C33 122.5(2) . . ?
N5 C34 C35 117.5(2) . . ?
C33 C34 C35 120.1(2) . . ?
N6 C35 C34 121.4(2) . . ?
N6 C36 C37 109.5(2) . . ?
C38 C37 C42 118.8(3) . . ?
C38 C37 C36 120.9(3) . . ?
C42 C37 C36 120.3(2) . . ?
C37 C38 C39 120.4(3) . . ?
C40 C39 C38 120.3(3) . . ?
C39 C40 C41 119.5(3) . . ?
C42 C41 C40 120.3(3) . . ?
C41 C42 C37 120.7(3) . . ?
F2 B1 F4 108.5(3) . . ?
F2 B1 F1 110.7(3) . . ?
F4 B1 F1 108.5(3) . . ?
F2 B1 F3 109.7(3) . . ?
F4 B1 F3 110.1(2) . . ?
F1 B1 F3 109.3(2) . . ?
F7 B2 F8 110.8(2) . . ?
F7 B2 F6 109.8(2) . . ?
F8 B2 F6 109.1(2) . . ?
F7 B2 F5 109.8(2) . . ?
F8 B2 F5 109.3(2) . . ?
F6 B2 F5 108.1(2) . . ?

_refine_diff_density_max         1.56
_refine_diff_density_min         -0.64
_refine_diff_density_rms         0.07

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_lp118
_database_code_depnum_ccdc_archive 'CCDC 1011863'
_audit_update_record             
;
2015-02-20 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C53 H48 B2 Cu2 F8 N8 O3'
_chemical_formula_weight         1145.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
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'
F F 0.0171 0.0103 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5600(6)
_cell_length_b                   20.2225(16)
_cell_length_c                   16.4909(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.726(5)
_cell_angle_gamma                90
_cell_volume                     2512.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2532
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      24.9

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_F_000             1172
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.930
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.589
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   '30 W microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker Apex II Quasar'
_diffrn_measurement_method       'ω & π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31718
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_av_R_equivalents  0.1129
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.014
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             4393
_reflns_number_gt                3218
_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       Apex2
_computing_cell_refinement       Apex2
_computing_data_reduction        Apex2
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    dimond3
_computing_publication_material  WinGX

_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)+12.9193P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   'F map'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4393
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.111
_refine_ls_R_factor_gt           0.078
_refine_ls_wR_factor_ref         0.166
_refine_ls_wR_factor_gt          0.155
_refine_ls_goodness_of_fit_ref   1.325
_refine_ls_restrained_S_all      1.325
_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 0.18019(10) 0.45206(4) 0.88600(5) 0.0212(2) Uani 1 1 d . . . . .
O1 O 0.1807(11) 0.5213(4) 0.9616(5) 0.020(2) Uani 0.5 1 d . . P . .
O2 O -0.0342(10) 0.4422(4) 0.9398(5) 0.021(2) Uani 0.5 1 d . . P . .
O3 O 0.0569(7) 0.5246(3) 1.0054(3) 0.0330(15) Uani 0.5 1 d . . P . .
N1 N 0.0570(7) 0.5107(3) 0.7998(3) 0.0235(13) Uani 1 1 d . . . . .
N2 N 0.0827(7) 0.3796(3) 0.7994(3) 0.0222(13) Uani 1 1 d . . . . .
N3 N 0.3125(7) 0.3936(3) 0.9689(3) 0.0241(13) Uani 1 1 d . . . . .
N4 N 0.4470(7) 0.4726(3) 0.8600(3) 0.0245(13) Uani 1 1 d . . . . .
C0 C 0.0569(7) 0.5246(3) 1.0054(3) 0.0330(15) Uani 0.5 1 d . . P . .
C1 C 0.0389(9) 0.5764(4) 0.8040(5) 0.0314(18) Uani 1 1 d . . . . .
H1 H 0.0873 0.5989 0.8513 0.038 Uiso 1 1 calc R U . . .
C2 C -0.0476(10) 0.6121(4) 0.7421(5) 0.041(2) Uani 1 1 d . . . . .
H2 H -0.0602 0.6587 0.7470 0.049 Uiso 1 1 calc R U . . .
C3 C -0.1158(12) 0.5800(4) 0.6728(6) 0.052(2) Uani 1 1 d . . . . .
H3 H -0.1722 0.6042 0.6285 0.062 Uiso 1 1 calc R U . . .
C4 C -0.1007(10) 0.5120(4) 0.6691(5) 0.038(2) Uani 1 1 d . . . . .
H4 H -0.1502 0.4884 0.6228 0.045 Uiso 1 1 calc R U . . .
C5 C -0.0127(9) 0.4790(3) 0.7333(4) 0.0249(16) Uani 1 1 d . . . . .
C6 C 0.0014(9) 0.4061(4) 0.7377(4) 0.0270(17) Uani 1 1 d . . . . .
H6 H -0.0503 0.3794 0.6946 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0797(9) 0.3069(3) 0.8054(5) 0.0299(17) Uani 1 1 d . . . . .
H7A H 0.0166 0.2881 0.7557 0.036 Uiso 1 1 calc R U . . .
H7B H 0.0147 0.2936 0.8525 0.036 Uiso 1 1 calc R U . . .
C8 C 0.2660(9) 0.2799(3) 0.8155(4) 0.0218(15) Uani 1 1 d . . . . .
C9 C 0.3843(10) 0.2925(4) 0.7590(4) 0.0330(18) Uani 1 1 d . . . . .
H9 H 0.3468 0.3164 0.7111 0.040 Uiso 1 1 calc R U . . .
C10 C 0.5594(10) 0.2704(4) 0.7710(5) 0.0366(19) Uani 1 1 d . . . . .
H10 H 0.6415 0.2806 0.7322 0.044 Uiso 1 1 calc R U . . .
C11 C 0.6132(10) 0.2340(4) 0.8386(5) 0.0351(19) Uani 1 1 d . . . . .
H11 H 0.7320 0.2186 0.8466 0.042 Uiso 1 1 calc R U . . .
C12 C 0.4947(10) 0.2199(4) 0.8947(5) 0.0348(19) Uani 1 1 d . . . . .
H12 H 0.5320 0.1944 0.9415 0.042 Uiso 1 1 calc R U . . .
C13 C 0.3207(9) 0.2422(3) 0.8842(4) 0.0262(16) Uani 1 1 d . . . . .
H13 H 0.2394 0.2320 0.9233 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2444(9) 0.3564(3) 1.0243(4) 0.0274(17) Uani 1 1 d . . . . .
H14 H 0.1193 0.3564 1.0267 0.033 Uiso 1 1 calc R U . . .
C15 C 0.3453(9) 0.3176(4) 1.0788(4) 0.0289(17) Uani 1 1 d . . . . .
H15 H 0.2915 0.2920 1.1184 0.035 Uiso 1 1 calc R U . . .
C16 C 0.5282(9) 0.3167(4) 1.0743(4) 0.0322(18) Uani 1 1 d . . . . .
H16 H 0.6020 0.2904 1.1108 0.039 Uiso 1 1 calc R U . . .
C17 C 0.6013(9) 0.3548(4) 1.0159(4) 0.0295(18) Uani 1 1 d . . . . .
H17 H 0.7257 0.3544 1.0112 0.035 Uiso 1 1 calc R U . . .
C18 C 0.4907(8) 0.3935(3) 0.9647(4) 0.0211(15) Uani 1 1 d . . . . .
C19 C 0.5561(9) 0.4378(3) 0.9052(4) 0.0254(17) Uani 1 1 d . . . . .
H19 H 0.6799 0.4410 0.8998 0.031 Uiso 1 1 calc R U . . .
C20 C 0.5164(9) 0.5205(4) 0.8042(4) 0.0311(18) Uani 1 1 d . . . . .
H20A H 0.6477 0.5197 0.8106 0.037 Uiso 1 1 calc R U . . .
H20B H 0.4773 0.5655 0.8185 0.037 Uiso 1 1 calc R U . . .
C21 C 0.4545(9) 0.5062(4) 0.7170(4) 0.0292(17) Uani 1 1 d . . . . .
C22 C 0.4840(10) 0.4444(4) 0.6840(5) 0.041(2) Uani 1 1 d . . . . .
H22 H 0.5450 0.4116 0.7168 0.049 Uiso 1 1 calc R U . . .
C23 C 0.4270(13) 0.4298(5) 0.6054(5) 0.056(3) Uani 1 1 d . . . . .
H23 H 0.4473 0.3871 0.5840 0.067 Uiso 1 1 calc R U . . .
C24 C 0.3412(14) 0.4766(6) 0.5578(5) 0.063(3) Uani 1 1 d . . . . .
H24 H 0.2994 0.4662 0.5033 0.075 Uiso 1 1 calc R U . . .
C25 C 0.3151(13) 0.5376(6) 0.5876(5) 0.064(3) Uani 1 1 d . . . . .
H25 H 0.2577 0.5701 0.5531 0.077 Uiso 1 1 calc R U . . .
C26 C 0.3701(10) 0.5539(4) 0.6671(5) 0.043(2) Uani 1 1 d . . . . .
H26 H 0.3505 0.5971 0.6873 0.051 Uiso 1 1 calc R U . . .
B1 B 0.9406(12) 0.2151(5) 0.0632(5) 0.034(2) Uani 1 1 d . . . . .
F1 F 0.9402(6) 0.2698(3) 0.1163(3) 0.0602(14) Uani 1 1 d . . . . .
F2 F 0.9252(6) 0.2389(3) -0.0144(3) 0.0569(14) Uani 1 1 d . . . . .
F3 F 0.7951(6) 0.1761(2) 0.0777(3) 0.0525(13) Uani 1 1 d . . . . .
F4 F 1.0952(6) 0.1813(2) 0.0803(3) 0.0516(13) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.875(8) . ?
Cu1 O2 1.921(8) . ?
Cu1 N3 2.010(6) . ?
Cu1 N1 2.019(6) . ?
Cu1 N2 2.134(5) . ?
Cu1 N4 2.137(6) . ?
O1 O3 1.230(10) . ?
O2 C0 1.149(10) 3_567 ?
O2 O3 1.149(10) 3_567 ?
O3 O2 1.149(10) 3_567 ?
O3 C0 1.318(12) 3_567 ?
O3 O3 1.318(12) 3_567 ?
N1 C1 1.338(8) . ?
N1 C5 1.340(8) . ?
N2 C6 1.263(8) . ?
N2 C7 1.475(8) . ?
N3 C14 1.321(9) . ?
N3 C18 1.355(8) . ?
N4 C19 1.278(8) . ?
N4 C20 1.463(9) . ?
C1 C2 1.372(10) . ?
C2 C3 1.377(12) . ?
C3 C4 1.383(11) . ?
C4 C5 1.376(10) . ?
C5 C6 1.480(10) . ?
C7 C8 1.507(9) . ?
C8 C9 1.368(10) . ?
C8 C13 1.398(9) . ?
C9 C10 1.396(10) . ?
C10 C11 1.370(10) . ?
C11 C12 1.370(11) . ?
C12 C13 1.388(10) . ?
C14 C15 1.375(9) . ?
C15 C16 1.391(10) . ?
C16 C17 1.383(10) . ?
C17 C18 1.381(9) . ?
C18 C19 1.445(10) . ?
C20 C21 1.503(9) . ?
C21 C26 1.388(10) . ?
C21 C22 1.389(11) . ?
C22 C23 1.364(11) . ?
C23 C24 1.360(13) . ?
C24 C25 1.349(14) . ?
C25 C26 1.384(12) . ?
B1 F2 1.362(9) . ?
B1 F4 1.364(10) . ?
B1 F3 1.390(9) . ?
B1 F1 1.412(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 74.1(4) . . ?
O1 Cu1 N3 90.8(3) . . ?
O2 Cu1 N3 90.9(3) . . ?
O1 Cu1 N1 90.3(3) . . ?
O2 Cu1 N1 91.6(3) . . ?
N3 Cu1 N1 177.4(2) . . ?
O1 Cu1 N2 159.9(3) . . ?
O2 Cu1 N2 88.9(3) . . ?
N3 Cu1 N2 100.2(2) . . ?
N1 Cu1 N2 79.5(2) . . ?
O1 Cu1 N4 92.2(3) . . ?
O2 Cu1 N4 163.5(3) . . ?
N3 Cu1 N4 80.0(2) . . ?
N1 Cu1 N4 97.6(2) . . ?
N2 Cu1 N4 106.2(2) . . ?
O3 O1 Cu1 118.1(6) . . ?
C0 O2 O3 0.0(6) 3_567 3_567 ?
C0 O2 Cu1 119.3(7) 3_567 . ?
O3 O2 Cu1 119.3(7) 3_567 . ?
O2 O3 O1 131.6(8) 3_567 . ?
O2 O3 C0 114.2(8) 3_567 3_567 ?
O1 O3 C0 113.5(8) . 3_567 ?
O2 O3 O3 114.2(8) 3_567 3_567 ?
O1 O3 O3 113.5(8) . 3_567 ?
C0 O3 O3 0.0(5) 3_567 3_567 ?
C1 N1 C5 118.9(7) . . ?
C1 N1 Cu1 126.1(5) . . ?
C5 N1 Cu1 115.0(5) . . ?
C6 N2 C7 117.9(6) . . ?
C6 N2 Cu1 111.5(5) . . ?
C7 N2 Cu1 130.2(4) . . ?
C14 N3 C18 118.7(6) . . ?
C14 N3 Cu1 127.3(5) . . ?
C18 N3 Cu1 114.1(5) . . ?
C19 N4 C20 119.0(6) . . ?
C19 N4 Cu1 110.5(5) . . ?
C20 N4 Cu1 130.4(4) . . ?
N1 C1 C2 121.9(8) . . ?
C1 C2 C3 119.5(8) . . ?
C2 C3 C4 118.7(8) . . ?
C5 C4 C3 119.0(8) . . ?
N1 C5 C4 122.0(7) . . ?
N1 C5 C6 114.5(6) . . ?
C4 C5 C6 123.3(7) . . ?
N2 C6 C5 119.4(6) . . ?
N2 C7 C8 110.4(6) . . ?
C9 C8 C13 119.1(6) . . ?
C9 C8 C7 121.0(6) . . ?
C13 C8 C7 119.9(6) . . ?
C8 C9 C10 120.6(7) . . ?
C11 C10 C9 120.1(7) . . ?
C12 C11 C10 119.7(7) . . ?
C11 C12 C13 120.9(7) . . ?
C12 C13 C8 119.5(7) . . ?
N3 C14 C15 123.4(7) . . ?
C14 C15 C16 118.2(7) . . ?
C17 C16 C15 119.1(7) . . ?
C18 C17 C16 119.0(7) . . ?
N3 C18 C17 121.6(7) . . ?
N3 C18 C19 115.5(6) . . ?
C17 C18 C19 122.8(6) . . ?
N4 C19 C18 119.9(6) . . ?
N4 C20 C21 112.0(6) . . ?
C26 C21 C22 118.3(7) . . ?
C26 C21 C20 121.6(7) . . ?
C22 C21 C20 120.0(7) . . ?
C23 C22 C21 121.2(8) . . ?
C24 C23 C22 119.8(9) . . ?
C25 C24 C23 120.2(9) . . ?
C24 C25 C26 121.5(9) . . ?
C25 C26 C21 118.9(8) . . ?
F2 B1 F4 112.1(7) . . ?
F2 B1 F3 110.8(6) . . ?
F4 B1 F3 110.9(7) . . ?
F2 B1 F1 107.6(7) . . ?
F4 B1 F1 108.0(6) . . ?
F3 B1 F1 107.2(7) . . ?

_refine_diff_density_max         0.45
_refine_diff_density_min         -0.58
_refine_diff_density_rms         0.10

_shelxl_version_number           2013-4

