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

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

data_077
_database_code_depnum_ccdc_archive 'CCDC 1414589'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H10 N4'
_chemical_formula_sum            'C5 H10 N4'
_chemical_formula_weight         126.17

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   10.67790(10)
_cell_length_b                   8.78930(10)
_cell_length_c                   15.0409(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1411.61(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4710
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      27.51

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7020
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_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            7341
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.313
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1615
_reflns_number_gt                1502
_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 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
;
SHELXL-2014/7 (Sheldrick, 2014),
PLATON (Spek, 2009)
;
_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)+(0.0527P)²+0.3140P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1615
_refine_ls_number_parameters     123
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0842
_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_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
N1 N 0.53132(5) 0.22948(7) 0.53787(4) 0.01375(17) Uani 1 1 d . U . . .
N2 N 0.63496(6) 0.21654(8) 0.48742(4) 0.01976(19) Uani 1 1 d . . . . .
N3 N 0.59936(7) 0.16158(8) 0.41126(4) 0.02107(19) Uani 1 1 d . . . . .
N4 N 0.47369(6) 0.13866(8) 0.41027(4) 0.01889(19) Uani 1 1 d . . . . .
C5 C 0.43424(8) 0.18171(9) 0.48936(5) 0.01622(19) Uani 1 1 d . . . . .
H5 H 0.3498(10) 0.1801(12) 0.5088(7) 0.024(3) Uiso 1 1 d . . . . .
C1 C 0.53770(7) 0.29162(9) 0.63023(5) 0.01631(19) Uani 1 1 d . U . . .
C2 C 0.64292(8) 0.21028(11) 0.67943(6) 0.0234(2) Uani 1 1 d . . . . .
H2A H 0.6437(10) 0.2457(13) 0.7410(8) 0.029(3) Uiso 1 1 d . . . . .
H2B H 0.7233(12) 0.2325(13) 0.6509(7) 0.034(3) Uiso 1 1 d . . . . .
H2C H 0.6294(11) 0.0988(15) 0.6799(8) 0.034(3) Uiso 1 1 d . . . . .
C3 C 0.41218(8) 0.26218(12) 0.67474(5) 0.0235(2) Uani 1 1 d . . . . .
H3A H 0.4171(11) 0.2962(13) 0.7358(8) 0.028(3) Uiso 1 1 d . . . . .
H3B H 0.3928(11) 0.1509(14) 0.6760(7) 0.030(3) Uiso 1 1 d . . . . .
H3C H 0.3442(11) 0.3179(14) 0.6447(8) 0.032(3) Uiso 1 1 d . . . . .
C4 C 0.56336(11) 0.46195(10) 0.62287(6) 0.0295(2) Uani 1 1 d . . . . .
H4A H 0.5707(12) 0.5027(15) 0.6825(9) 0.040(3) Uiso 1 1 d . . . . .
H4B H 0.6412(11) 0.4812(14) 0.5905(7) 0.033(3) Uiso 1 1 d . . . . .
H4C H 0.4899(12) 0.5121(15) 0.5912(8) 0.036(3) Uiso 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
N1 C5 1.3354(10) . ?
N1 N2 1.3468(9) . ?
N1 C1 1.4942(10) . ?
N2 N3 1.3000(10) . ?
N3 N4 1.3569(10) . ?
N4 C5 1.3175(11) . ?
C5 H5 0.947(11) . ?
C1 C3 1.5204(11) . ?
C1 C2 1.5234(11) . ?
C1 C4 1.5259(12) . ?
C2 H2A 0.977(12) . ?
C2 H2B 0.979(12) . ?
C2 H2C 0.991(13) . ?
C3 H3A 0.968(12) . ?
C3 H3B 1.000(12) . ?
C3 H3C 0.985(12) . ?
C4 H4A 0.969(13) . ?
C4 H4B 0.978(12) . ?
C4 H4C 1.018(13) . ?

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
C5 N1 N2 107.67(6) . . ?
C5 N1 C1 131.17(6) . . ?
N2 N1 C1 121.15(6) . . ?
N3 N2 N1 106.71(6) . . ?
N2 N3 N4 110.73(6) . . ?
C5 N4 N3 105.29(6) . . ?
N4 C5 N1 109.60(7) . . ?
N4 C5 H5 125.3(6) . . ?
N1 C5 H5 125.1(6) . . ?
N1 C1 C3 107.87(6) . . ?
N1 C1 C2 108.29(6) . . ?
C3 C1 C2 110.87(7) . . ?
N1 C1 C4 107.42(6) . . ?
C3 C1 C4 110.93(7) . . ?
C2 C1 C4 111.30(7) . . ?
C1 C2 H2A 108.5(7) . . ?
C1 C2 H2B 109.9(7) . . ?
H2A C2 H2B 110.1(10) . . ?
C1 C2 H2C 111.1(7) . . ?
H2A C2 H2C 108.1(9) . . ?
H2B C2 H2C 109.2(10) . . ?
C1 C3 H3A 108.5(7) . . ?
C1 C3 H3B 110.9(7) . . ?
H3A C3 H3B 107.2(9) . . ?
C1 C3 H3C 111.3(7) . . ?
H3A C3 H3C 108.8(10) . . ?
H3B C3 H3C 110.0(10) . . ?
C1 C4 H4A 108.0(8) . . ?
C1 C4 H4B 111.0(7) . . ?
H4A C4 H4B 109.2(10) . . ?
C1 C4 H4C 108.7(7) . . ?
H4A C4 H4C 109.6(10) . . ?
H4B C4 H4C 110.3(10) . . ?

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
C5 N1 N2 N3 -0.35(9) . . . . ?
C1 N1 N2 N3 -179.17(7) . . . . ?
N1 N2 N3 N4 0.33(9) . . . . ?
N2 N3 N4 C5 -0.18(9) . . . . ?
N3 N4 C5 N1 -0.05(9) . . . . ?
N2 N1 C5 N4 0.25(9) . . . . ?
C1 N1 C5 N4 178.91(7) . . . . ?
C5 N1 C1 C3 12.54(11) . . . . ?
N2 N1 C1 C3 -168.96(7) . . . . ?
C5 N1 C1 C2 132.60(8) . . . . ?
N2 N1 C1 C2 -48.90(9) . . . . ?
C5 N1 C1 C4 -107.10(9) . . . . ?
N2 N1 C1 C4 71.40(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5 N2 0.947(11) 2.468(11) 3.3367(11) 152.4(9) 4_456

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_71
_database_code_depnum_ccdc_archive 'CCDC 1414590'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H84 Cu2 N32 O2, 4(B F4)'
_chemical_formula_sum            'C20 H42 B2 Cu F8 N16 O'
_chemical_formula_weight         759.85

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.29880(10)
_cell_length_b                   12.57020(10)
_cell_length_c                   12.58490(10)
_cell_angle_alpha                89.7679(5)
_cell_angle_beta                 76.6828(5)
_cell_angle_gamma                85.2409(5)
_cell_volume                     1733.14(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9808
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      30.17

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             786
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.716
_shelx_estimated_absorpt_T_min   0.763
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7072
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_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            37750
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.626
_diffrn_reflns_theta_max         30.186
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             10164
_reflns_number_gt                9342
_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 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
;
SHELXL-2014/7 (Sheldrick, 2014),
PLATON (Spek, 2009)
;
_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)+(0.0415P)²+0.9456P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10164
_refine_ls_number_parameters     516
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.153
_refine_ls_shift/su_max          0.003
_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 0.16889(2) 0.53989(2) 0.05524(2) 0.01202(4) Uani 1 1 d . . . . .
C11 C 0.26038(12) 0.92217(9) 0.22834(10) 0.0183(2) Uani 1 1 d . . . . .
C12 C 0.34468(16) 0.95133(11) 0.12207(12) 0.0295(3) Uani 1 1 d . . . . .
H12A H 0.4144 0.8975 0.1035 0.044 Uiso 1 1 calc R U . . .
H12B H 0.3740 1.0214 0.1303 0.044 Uiso 1 1 calc R U . . .
H12C H 0.3002 0.9540 0.0637 0.044 Uiso 1 1 calc R U . . .
C13 C 0.14636(15) 0.99996(13) 0.25532(16) 0.0362(4) Uani 1 1 d . . . . .
H13A H 0.1030 0.9981 0.1964 0.054 Uiso 1 1 calc R U . . .
H13B H 0.1699 1.0723 0.2630 0.054 Uiso 1 1 calc R U . . .
H13C H 0.0929 0.9795 0.3239 0.054 Uiso 1 1 calc R U . . .
C14 C 0.32693(13) 0.91628(11) 0.32062(11) 0.0246(3) Uani 1 1 d . . . . .
H14A H 0.2703 0.8988 0.3887 0.037 Uiso 1 1 calc R U . . .
H14B H 0.3583 0.9854 0.3292 0.037 Uiso 1 1 calc R U . . .
H14C H 0.3951 0.8609 0.3035 0.037 Uiso 1 1 calc R U . . .
N11 N 0.22045(9) 0.81388(8) 0.21290(8) 0.01493(18) Uani 1 1 d . . . . .
N12 N 0.14978(10) 0.76340(9) 0.29636(8) 0.0193(2) Uani 1 1 d . . . . .
N13 N 0.12912(10) 0.67347(9) 0.25853(8) 0.01838(19) Uani 1 1 d . . . . .
N14 N 0.18502(9) 0.66410(8) 0.15040(8) 0.01441(18) Uani 1 1 d . . . . .
C15 C 0.24117(10) 0.75176(9) 0.12436(9) 0.0149(2) Uani 1 1 d . . . . .
H15 H 0.2884 0.7677 0.0543 0.018 Uiso 1 1 calc R U . . .
C21 C 0.22252(13) 0.34082(10) 0.43662(10) 0.0210(2) Uani 1 1 d . . . . .
C22 C 0.33310(13) 0.39889(12) 0.44292(11) 0.0261(3) Uani 1 1 d . . . . .
H22A H 0.3995 0.3793 0.3792 0.039 Uiso 1 1 calc R U . . .
H22B H 0.3594 0.3788 0.5097 0.039 Uiso 1 1 calc R U . . .
H22C H 0.3118 0.4761 0.4439 0.039 Uiso 1 1 calc R U . . .
C23 C 0.11491(15) 0.37182(14) 0.53168(12) 0.0323(3) Uani 1 1 d . . . . .
H23A H 0.0936 0.4490 0.5311 0.048 Uiso 1 1 calc R U . . .
H23B H 0.1371 0.3527 0.6005 0.048 Uiso 1 1 calc R U . . .
H23C H 0.0448 0.3338 0.5246 0.048 Uiso 1 1 calc R U . . .
C24 C 0.2560(2) 0.22043(12) 0.42819(14) 0.0421(4) Uani 1 1 d . . . . .
H24A H 0.1824 0.1834 0.4305 0.063 Uiso 1 1 calc R U . . .
H24B H 0.2916 0.1975 0.4894 0.063 Uiso 1 1 calc R U . . .
H24C H 0.3154 0.2030 0.3592 0.063 Uiso 1 1 calc R U . . .
N21 N 0.18514(10) 0.37389(8) 0.33373(8) 0.01734(19) Uani 1 1 d . . . . .
N22 N 0.09007(13) 0.33226(11) 0.30594(10) 0.0309(3) Uani 1 1 d . . . . .
N23 N 0.07684(12) 0.37576(10) 0.21584(10) 0.0273(3) Uani 1 1 d . . . . .
N24 N 0.16318(9) 0.44519(8) 0.18389(8) 0.01547(18) Uani 1 1 d . . . . .
C25 C 0.22980(11) 0.44270(9) 0.25779(9) 0.0150(2) Uani 1 1 d . . . . .
H25 H 0.2976 0.4830 0.2567 0.018 Uiso 1 1 calc R U . . .
C31 C 0.20899(11) 0.14513(9) -0.14757(10) 0.0166(2) Uani 1 1 d . . . . .
C32 C 0.21738(15) 0.13881(11) -0.26983(11) 0.0275(3) Uani 1 1 d . . . . .
H32A H 0.1370 0.1593 -0.2842 0.041 Uiso 1 1 calc R U . . .
H32B H 0.2444 0.0656 -0.2964 0.041 Uiso 1 1 calc R U . . .
H32C H 0.2761 0.1875 -0.3076 0.041 Uiso 1 1 calc R U . . .
C33 C 0.33312(13) 0.11398(11) -0.12308(12) 0.0251(3) Uani 1 1 d . . . . .
H33A H 0.3930 0.1605 -0.1631 0.038 Uiso 1 1 calc R U . . .
H33B H 0.3590 0.0396 -0.1458 0.038 Uiso 1 1 calc R U . . .
H33C H 0.3271 0.1218 -0.0445 0.038 Uiso 1 1 calc R U . . .
C34 C 0.11086(13) 0.07851(10) -0.08352(13) 0.0271(3) Uani 1 1 d . . . . .
H34A H 0.1069 0.0859 -0.0053 0.041 Uiso 1 1 calc R U . . .
H34B H 0.1308 0.0033 -0.1059 0.041 Uiso 1 1 calc R U . . .
H34C H 0.0317 0.1034 -0.0981 0.041 Uiso 1 1 calc R U . . .
N31 N 0.17351(9) 0.25912(8) -0.11214(8) 0.01300(17) Uani 1 1 d . . . . .
N32 N 0.09154(9) 0.31892(8) -0.15421(8) 0.01611(18) Uani 1 1 d . . . . .
N33 N 0.07497(9) 0.41125(8) -0.10615(8) 0.01537(18) Uani 1 1 d . . . . .
N34 N 0.14569(9) 0.41264(8) -0.03210(8) 0.01311(17) Uani 1 1 d . . . . .
C35 C 0.20530(11) 0.31729(9) -0.03684(10) 0.0154(2) Uani 1 1 d . . . . .
H35 H 0.2613 0.2942 0.0061 0.018 Uiso 1 1 calc R U . . .
C41 C 0.23436(12) 0.75550(10) -0.34044(10) 0.0184(2) Uani 1 1 d . . . . .
C42 C 0.13817(12) 0.83960(10) -0.36394(11) 0.0209(2) Uani 1 1 d . . . . .
H42A H 0.0587 0.8097 -0.3500 0.031 Uiso 1 1 calc R U . . .
H42B H 0.1613 0.8607 -0.4405 0.031 Uiso 1 1 calc R U . . .
H42C H 0.1329 0.9022 -0.3164 0.031 Uiso 1 1 calc R U . . .
C43 C 0.24609(18) 0.65835(12) -0.41408(11) 0.0333(3) Uani 1 1 d . . . . .
H43A H 0.3087 0.6058 -0.3984 0.050 Uiso 1 1 calc R U . . .
H43B H 0.2695 0.6796 -0.4906 0.050 Uiso 1 1 calc R U . . .
H43C H 0.1677 0.6267 -0.4009 0.050 Uiso 1 1 calc R U . . .
C44 C 0.35607(13) 0.80304(14) -0.35054(12) 0.0303(3) Uani 1 1 d . . . . .
H44A H 0.3453 0.8641 -0.3000 0.045 Uiso 1 1 calc R U . . .
H44B H 0.3856 0.8268 -0.4255 0.045 Uiso 1 1 calc R U . . .
H44C H 0.4156 0.7488 -0.3326 0.045 Uiso 1 1 calc R U . . .
N41 N 0.19173(9) 0.72069(8) -0.22440(8) 0.01425(18) Uani 1 1 d . . . . .
N42 N 0.11418(10) 0.78486(8) -0.14930(8) 0.0182(2) Uani 1 1 d . . . . .
N43 N 0.09728(10) 0.73561(8) -0.05781(8) 0.01763(19) Uani 1 1 d . . . . .
N44 N 0.16352(9) 0.63894(8) -0.07141(8) 0.01314(17) Uani 1 1 d . . . . .
C45 C 0.22154(11) 0.63149(9) -0.17543(9) 0.0147(2) Uani 1 1 d . . . . .
H45 H 0.2751 0.5728 -0.2094 0.018 Uiso 1 1 calc R U . . .
B1 B 0.47955(14) 0.37631(13) 0.71260(12) 0.0241(3) Uani 1 1 d D U . . .
F1A F 0.6003(4) 0.3787(4) 0.7114(6) 0.0287(13) Uani 0.46(2) 1 d D U P A 1
F2A F 0.4402(5) 0.4699(3) 0.6626(6) 0.0355(12) Uani 0.46(2) 1 d D U P A 1
F3A F 0.4584(7) 0.2878(5) 0.6593(7) 0.0288(12) Uani 0.46(2) 1 d D U P A 1
F4A F 0.4023(6) 0.3821(8) 0.8161(5) 0.0587(18) Uani 0.46(2) 1 d D U P A 1
F1B F 0.6009(5) 0.3871(6) 0.7085(7) 0.063(2) Uani 0.54(2) 1 d D U P A 2
F2B F 0.4267(6) 0.4677(4) 0.6847(8) 0.0657(16) Uani 0.54(2) 1 d D U P A 2
F3B F 0.4701(8) 0.2922(5) 0.6456(7) 0.0494(16) Uani 0.54(2) 1 d D U P A 2
F4B F 0.4333(13) 0.3505(10) 0.8210(5) 0.099(3) Uani 0.54(2) 1 d D U P A 2
B2 B 0.48092(15) 0.25304(14) 0.11681(14) 0.0294(3) Uani 1 1 d D U . . .
F5 F 0.49285(9) 0.33726(7) 0.18092(8) 0.0329(2) Uani 1 1 d D U . . .
F6A F 0.50047(11) 0.29543(11) 0.00748(9) 0.0309(3) Uani 0.779(3) 1 d D U P B 1
F7A F 0.5646(2) 0.16974(15) 0.11472(19) 0.0434(5) Uani 0.779(3) 1 d D U P B 1
F8A F 0.36076(11) 0.22433(9) 0.14044(10) 0.0306(3) Uani 0.779(3) 1 d D U P B 1
F6B F 0.4327(6) 0.2332(5) 0.0485(5) 0.060(2) Uani 0.221(3) 1 d D U P B 2
F7B F 0.6061(5) 0.1908(5) 0.1070(5) 0.0266(12) Uani 0.221(3) 1 d D U P B 2
F8B F 0.4236(5) 0.1844(4) 0.2199(5) 0.0579(19) Uani 0.221(3) 1 d D U P B 2
O1W O 0.37125(9) 0.51101(9) -0.00774(10) 0.0278(2) Uani 1 1 d D . . . .
H1W H 0.397(2) 0.4642(14) -0.0548(16) 0.042 Uiso 1 1 d D U . . .
H2W H 0.4155(18) 0.5619(13) -0.0212(17) 0.042 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N24 1.9979(10) . ?
Cu1 N34 2.0130(10) . ?
Cu1 N14 2.0169(10) . ?
Cu1 N44 2.0274(9) . ?
Cu1 O1W 2.2400(10) . ?
C11 N11 1.4962(15) . ?
C11 C12 1.5157(19) . ?
C11 C14 1.5205(17) . ?
C11 C13 1.5243(19) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N11 C15 1.3276(14) . ?
N11 N12 1.3549(14) . ?
N12 N13 1.2878(15) . ?
N13 N14 1.3629(14) . ?
N14 C15 1.3196(15) . ?
C15 H15 0.9500 . ?
C21 N21 1.4987(15) . ?
C21 C22 1.516(2) . ?
C21 C23 1.522(2) . ?
C21 C24 1.5273(19) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N21 C25 1.3266(15) . ?
N21 N22 1.3483(16) . ?
N22 N23 1.2910(16) . ?
N23 N24 1.3538(14) . ?
N24 C25 1.3231(15) . ?
C25 H25 0.9500 . ?
C31 N31 1.4968(14) . ?
C31 C32 1.5216(18) . ?
C31 C34 1.5223(17) . ?
C31 C33 1.5240(18) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
N31 C35 1.3295(15) . ?
N31 N32 1.3455(13) . ?
N32 N33 1.2905(14) . ?
N33 N34 1.3612(13) . ?
N34 C35 1.3199(15) . ?
C35 H35 0.9500 . ?
C41 N41 1.5039(15) . ?
C41 C43 1.5145(19) . ?
C41 C44 1.5230(19) . ?
C41 C42 1.5301(17) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
N41 C45 1.3334(14) . ?
N41 N42 1.3488(13) . ?
N42 N43 1.2876(14) . ?
N43 N44 1.3631(13) . ?
N44 C45 1.3220(15) . ?
C45 H45 0.9500 . ?
B1 F2B 1.334(6) . ?
B1 F1A 1.363(5) . ?
B1 F3A 1.368(6) . ?
B1 F1B 1.378(6) . ?
B1 F3B 1.382(6) . ?
B1 F4A 1.389(6) . ?
B1 F4B 1.391(5) . ?
B1 F2A 1.419(4) . ?
B2 F6B 1.157(4) . ?
B2 F7A 1.348(2) . ?
B2 F5 1.3677(17) . ?
B2 F8A 1.399(2) . ?
B2 F6A 1.449(2) . ?
B2 F7B 1.538(6) . ?
B2 F8B 1.595(5) . ?
O1W H1W 0.823(14) . ?
O1W H2W 0.837(15) . ?

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
N24 Cu1 N34 88.73(4) . . ?
N24 Cu1 N14 88.63(4) . . ?
N34 Cu1 N14 176.59(4) . . ?
N24 Cu1 N44 176.42(4) . . ?
N34 Cu1 N44 91.77(4) . . ?
N14 Cu1 N44 90.74(4) . . ?
N24 Cu1 O1W 94.57(4) . . ?
N34 Cu1 O1W 89.58(4) . . ?
N14 Cu1 O1W 92.76(4) . . ?
N44 Cu1 O1W 88.98(4) . . ?
N11 C11 C12 107.63(10) . . ?
N11 C11 C14 108.11(10) . . ?
C12 C11 C14 110.89(12) . . ?
N11 C11 C13 107.53(11) . . ?
C12 C11 C13 110.74(13) . . ?
C14 C11 C13 111.76(11) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 N11 N12 108.18(10) . . ?
C15 N11 C11 130.44(10) . . ?
N12 N11 C11 121.37(10) . . ?
N13 N12 N11 107.28(10) . . ?
N12 N13 N14 109.54(10) . . ?
C15 N14 N13 106.67(10) . . ?
C15 N14 Cu1 129.90(8) . . ?
N13 N14 Cu1 123.33(8) . . ?
N14 C15 N11 108.33(10) . . ?
N14 C15 H15 125.8 . . ?
N11 C15 H15 125.8 . . ?
N21 C21 C22 107.77(10) . . ?
N21 C21 C23 107.42(11) . . ?
C22 C21 C23 111.55(11) . . ?
N21 C21 C24 107.28(10) . . ?
C22 C21 C24 110.19(13) . . ?
C23 C21 C24 112.38(13) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C25 N21 N22 108.34(10) . . ?
C25 N21 C21 131.11(11) . . ?
N22 N21 C21 120.54(10) . . ?
N23 N22 N21 107.48(10) . . ?
N22 N23 N24 109.21(10) . . ?
C25 N24 N23 107.13(10) . . ?
C25 N24 Cu1 129.53(8) . . ?
N23 N24 Cu1 123.08(8) . . ?
N24 C25 N21 107.83(10) . . ?
N24 C25 H25 126.1 . . ?
N21 C25 H25 126.1 . . ?
N31 C31 C32 107.41(10) . . ?
N31 C31 C34 107.50(10) . . ?
C32 C31 C34 111.86(12) . . ?
N31 C31 C33 107.59(10) . . ?
C32 C31 C33 110.46(11) . . ?
C34 C31 C33 111.78(11) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C35 N31 N32 108.36(9) . . ?
C35 N31 C31 130.82(10) . . ?
N32 N31 C31 120.73(9) . . ?
N33 N32 N31 107.35(9) . . ?
N32 N33 N34 109.51(9) . . ?
C35 N34 N33 106.56(9) . . ?
C35 N34 Cu1 126.54(8) . . ?
N33 N34 Cu1 126.58(7) . . ?
N34 C35 N31 108.21(10) . . ?
N34 C35 H35 125.9 . . ?
N31 C35 H35 125.9 . . ?
N41 C41 C43 107.82(10) . . ?
N41 C41 C44 107.87(10) . . ?
C43 C41 C44 111.93(12) . . ?
N41 C41 C42 107.71(10) . . ?
C43 C41 C42 110.69(11) . . ?
C44 C41 C42 110.65(11) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C45 N41 N42 108.36(9) . . ?
C45 N41 C41 130.35(10) . . ?
N42 N41 C41 121.25(9) . . ?
N43 N42 N41 107.28(9) . . ?
N42 N43 N44 109.78(9) . . ?
C45 N44 N43 106.49(9) . . ?
C45 N44 Cu1 131.33(8) . . ?
N43 N44 Cu1 122.08(7) . . ?
N44 C45 N41 108.09(10) . . ?
N44 C45 H45 126.0 . . ?
N41 C45 H45 126.0 . . ?
F1A B1 F3A 111.6(4) . . ?
F2B B1 F1B 109.9(4) . . ?
F2B B1 F3B 112.0(4) . . ?
F1B B1 F3B 109.5(5) . . ?
F1A B1 F4A 114.6(4) . . ?
F3A B1 F4A 108.7(4) . . ?
F2B B1 F4B 112.6(5) . . ?
F1B B1 F4B 103.1(6) . . ?
F3B B1 F4B 109.4(4) . . ?
F1A B1 F2A 108.9(3) . . ?
F3A B1 F2A 109.9(4) . . ?
F4A B1 F2A 102.7(4) . . ?
F6B B2 F5 140.1(3) . . ?
F7A B2 F5 114.33(16) . . ?
F7A B2 F8A 113.52(17) . . ?
F5 B2 F8A 111.19(12) . . ?
F7A B2 F6A 107.45(16) . . ?
F5 B2 F6A 104.52(14) . . ?
F8A B2 F6A 104.87(14) . . ?
F6B B2 F7B 114.0(4) . . ?
F5 B2 F7B 100.0(3) . . ?
F6B B2 F8B 106.6(5) . . ?
F5 B2 F8B 92.6(2) . . ?
F7B B2 F8B 90.5(3) . . ?
Cu1 O1W H1W 118.3(15) . . ?
Cu1 O1W H2W 121.1(14) . . ?
H1W O1W H2W 108.4(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
C12 C11 N11 C15 -5.14(17) . . . . ?
C14 C11 N11 C15 -124.98(13) . . . . ?
C13 C11 N11 C15 114.21(15) . . . . ?
C12 C11 N11 N12 176.04(11) . . . . ?
C14 C11 N11 N12 56.20(14) . . . . ?
C13 C11 N11 N12 -64.61(15) . . . . ?
C15 N11 N12 N13 0.10(13) . . . . ?
C11 N11 N12 N13 179.15(10) . . . . ?
N11 N12 N13 N14 -0.32(13) . . . . ?
N12 N13 N14 C15 0.43(13) . . . . ?
N12 N13 N14 Cu1 -176.16(8) . . . . ?
N13 N14 C15 N11 -0.36(13) . . . . ?
Cu1 N14 C15 N11 175.92(8) . . . . ?
N12 N11 C15 N14 0.17(13) . . . . ?
C11 N11 C15 N14 -178.77(11) . . . . ?
C22 C21 N21 C25 -2.20(18) . . . . ?
C23 C21 N21 C25 118.12(15) . . . . ?
C24 C21 N21 C25 -120.85(16) . . . . ?
C22 C21 N21 N22 178.50(12) . . . . ?
C23 C21 N21 N22 -61.18(16) . . . . ?
C24 C21 N21 N22 59.85(18) . . . . ?
C25 N21 N22 N23 -0.64(17) . . . . ?
C21 N21 N22 N23 178.81(12) . . . . ?
N21 N22 N23 N24 0.42(17) . . . . ?
N22 N23 N24 C25 -0.04(16) . . . . ?
N22 N23 N24 Cu1 -174.69(10) . . . . ?
N23 N24 C25 N21 -0.35(14) . . . . ?
Cu1 N24 C25 N21 173.83(8) . . . . ?
N22 N21 C25 N24 0.61(14) . . . . ?
C21 N21 C25 N24 -178.76(12) . . . . ?
C32 C31 N31 C35 -144.86(13) . . . . ?
C34 C31 N31 C35 94.60(15) . . . . ?
C33 C31 N31 C35 -25.93(16) . . . . ?
C32 C31 N31 N32 39.03(14) . . . . ?
C34 C31 N31 N32 -81.51(13) . . . . ?
C33 C31 N31 N32 157.96(10) . . . . ?
C35 N31 N32 N33 0.51(13) . . . . ?
C31 N31 N32 N33 177.41(10) . . . . ?
N31 N32 N33 N34 -0.12(13) . . . . ?
N32 N33 N34 C35 -0.31(13) . . . . ?
N32 N33 N34 Cu1 173.55(8) . . . . ?
N33 N34 C35 N31 0.62(13) . . . . ?
Cu1 N34 C35 N31 -173.25(7) . . . . ?
N32 N31 C35 N34 -0.70(13) . . . . ?
C31 N31 C35 N34 -177.18(10) . . . . ?
C43 C41 N41 C45 38.63(17) . . . . ?
C44 C41 N41 C45 -82.42(16) . . . . ?
C42 C41 N41 C45 158.12(12) . . . . ?
C43 C41 N41 N42 -144.12(12) . . . . ?
C44 C41 N41 N42 94.83(13) . . . . ?
C42 C41 N41 N42 -24.63(15) . . . . ?
C45 N41 N42 N43 -0.27(13) . . . . ?
C41 N41 N42 N43 -178.06(10) . . . . ?
N41 N42 N43 N44 0.19(13) . . . . ?
N42 N43 N44 C45 -0.04(13) . . . . ?
N42 N43 N44 Cu1 176.72(8) . . . . ?
N43 N44 C45 N41 -0.13(13) . . . . ?
Cu1 N44 C45 N41 -176.47(8) . . . . ?
N42 N41 C45 N44 0.25(13) . . . . ?
C41 N41 C45 N44 177.77(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15 F6A 0.95 2.40 3.0192(17) 123. 2_665
C15 H15 F7A 0.95 2.54 3.484(3) 170. 2_665
C15 H15 F7B 0.95 2.19 3.139(6) 178. 2_665
C25 H25 F1A 0.95 2.25 3.153(6) 158. 2_666
C25 H25 F1B 0.95 2.17 3.078(7) 159. 2_666
C35 H35 F8A 0.95 2.36 3.2972(17) 167.0 .
C35 H35 F6B 0.95 2.20 3.112(4) 160.0 .
C45 H45 F2A 0.95 2.45 3.357(7) 161. 1_554
C45 H45 F2B 0.95 2.25 3.173(7) 165. 1_554
O1W H1W F4A 0.823(14) 1.916(17) 2.691(7) 156(2) 1_554
O1W H1W F4B 0.823(14) 2.070(17) 2.884(10) 170(2) 1_554
O1W H1W F6A 0.823(14) 2.54(2) 2.9967(16) 116.0(18) .
O1W H2W F5 0.837(15) 2.441(19) 3.1073(15) 137.2(18) 2_665
O1W H2W F6A 0.837(15) 2.123(15) 2.9339(17) 163(2) 2_665

_refine_diff_density_max         0.764
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_00
_database_code_depnum_ccdc_archive 'CCDC 1414591'
_audit_update_record             
;
2015-09-01 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H72 Cu3 N24 O6, 6(B F4)'
_chemical_formula_sum            'C30 H72 B6 Cu3 F24 N24 O6'
_chemical_formula_weight         1576.59

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'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'
'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'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-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'
'-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'

_cell_length_a                   13.99620(10)
_cell_length_b                   13.99620(10)
_cell_length_c                   28.8072(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4887.11(9)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7616
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      30.05

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_F_000             2403
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.097
_shelx_estimated_absorpt_T_min   0.771
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6919
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_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            11742
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.823
_diffrn_reflns_theta_max         30.056
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3143
_reflns_number_gt                2825
_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 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
;
SHELXL-2014/7 (Sheldrick, 2014),
PLATON (Spek, 2009)
;
_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)+(0.0537P)²+11.2143P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3143
_refine_ls_number_parameters     152
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.050
_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 0.0000 0.0000 0.0000 0.01106(10) Uani 1 6 d S T P . .
Cu2 Cu 0.0000 0.0000 0.13419(2) 0.01504(10) Uani 1 3 d S T P . .
O1W O 0.12906(11) 0.03257(11) 0.17685(5) 0.0311(3) Uani 1 1 d D . . . .
H1W H 0.1849(19) 0.032(3) 0.1667(10) 0.057(9) Uiso 1 1 d D . . . .
H2W H 0.152(2) 0.084(2) 0.1962(9) 0.057(9) Uiso 1 1 d D . . . .
N1 N 0.21824(13) 0.29694(12) 0.06707(6) 0.0287(3) Uani 1 1 d . . . . .
N2 N 0.17117(14) 0.23555(13) 0.10458(7) 0.0331(4) Uani 1 1 d . . . . .
N3 N 0.09686(12) 0.13814(12) 0.09060(6) 0.0280(3) Uani 1 1 d . . . . .
N4 N 0.09704(11) 0.13746(12) 0.04347(6) 0.0271(3) Uani 1 1 d . . . . .
C5 C 0.17250(13) 0.23552(13) 0.03019(7) 0.0251(3) Uani 1 1 d . . . . .
H5 H 0.1914 0.2589 -0.0011 0.030 Uiso 1 1 calc R U . . .
C1 C 0.31254(17) 0.41384(14) 0.06658(7) 0.0324(4) Uani 1 1 d . . . . .
C2 C 0.3133(4) 0.4638(2) 0.11328(10) 0.0858(14) Uani 1 1 d . . . . .
H2A H 0.2413 0.4573 0.1188 0.129 Uiso 1 1 calc R U . . .
H2B H 0.3707 0.5418 0.1135 0.129 Uiso 1 1 calc R U . . .
H2C H 0.3286 0.4245 0.1377 0.129 Uiso 1 1 calc R U . . .
C3 C 0.29024(18) 0.47475(16) 0.02863(8) 0.0370(4) Uani 1 1 d . . . . .
H3A H 0.2892 0.4417 -0.0015 0.056 Uiso 1 1 calc R U . . .
H3B H 0.3484 0.5525 0.0287 0.056 Uiso 1 1 calc R U . . .
H3C H 0.2187 0.4695 0.0341 0.056 Uiso 1 1 calc R U . . .
C4 C 0.41569(18) 0.4082(2) 0.05683(13) 0.0598(8) Uani 1 1 d . . . . .
H4A H 0.4267 0.3667 0.0816 0.090 Uiso 1 1 calc R U . . .
H4B H 0.4794 0.4831 0.0555 0.090 Uiso 1 1 calc R U . . .
H4C H 0.4079 0.3712 0.0270 0.090 Uiso 1 1 calc R U . . .
B1 B 0.9390(2) 0.28354(18) 0.09582(8) 0.0311(4) Uani 1 1 d . . . . .
F1 F 1.02666(12) 0.34394(12) 0.06683(5) 0.0474(4) Uani 1 1 d . . . . .
F2 F 0.87175(14) 0.32995(13) 0.09724(6) 0.0595(5) Uani 1 1 d . . . . .
F3 F 0.97467(17) 0.27902(14) 0.14065(5) 0.0601(5) Uani 1 1 d . . . . .
F4 F 0.87972(14) 0.17719(12) 0.07931(6) 0.0518(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 N4 2.1216(17) 11 ?
Cu1 N4 2.1216(17) 2 ?
Cu1 N4 2.1216(17) . ?
Cu1 N4 2.1216(17) 10 ?
Cu1 N4 2.1217(17) 12 ?
Cu1 N4 2.1217(17) 3 ?
Cu2 O1W 2.0389(15) . ?
Cu2 O1W 2.0389(15) 2 ?
Cu2 O1W 2.0389(15) 3 ?
Cu2 N3 2.1288(15) 2 ?
Cu2 N3 2.1288(15) . ?
Cu2 N3 2.1289(15) 3 ?
O1W H1W 0.836(17) . ?
O1W H2W 0.835(17) . ?
N1 C5 1.314(3) . ?
N1 N2 1.332(2) . ?
N1 C1 1.503(2) . ?
N2 N3 1.298(2) . ?
N3 N4 1.358(2) . ?
N4 C5 1.302(2) . ?
C5 H5 0.9500 . ?
C1 C4 1.511(3) . ?
C1 C3 1.512(3) . ?
C1 C2 1.513(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
B1 F1 1.372(2) . ?
B1 F4 1.377(3) . ?
B1 F2 1.385(2) . ?
B1 F3 1.398(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
N4 Cu1 N4 180.00(10) 11 2 ?
N4 Cu1 N4 91.29(6) 11 . ?
N4 Cu1 N4 88.71(6) 2 . ?
N4 Cu1 N4 88.71(6) 11 10 ?
N4 Cu1 N4 91.29(6) 2 10 ?
N4 Cu1 N4 180.0 . 10 ?
N4 Cu1 N4 88.70(6) 11 12 ?
N4 Cu1 N4 91.30(6) 2 12 ?
N4 Cu1 N4 91.29(6) . 12 ?
N4 Cu1 N4 88.70(6) 10 12 ?
N4 Cu1 N4 91.30(6) 11 3 ?
N4 Cu1 N4 88.70(6) 2 3 ?
N4 Cu1 N4 88.71(6) . 3 ?
N4 Cu1 N4 91.30(6) 10 3 ?
N4 Cu1 N4 180.00(11) 12 3 ?
O1W Cu2 O1W 87.43(6) . 2 ?
O1W Cu2 O1W 87.43(6) . 3 ?
O1W Cu2 O1W 87.43(6) 2 3 ?
O1W Cu2 N3 177.52(5) . 2 ?
O1W Cu2 N3 93.54(6) 2 2 ?
O1W Cu2 N3 90.33(6) 3 2 ?
O1W Cu2 N3 93.54(6) . . ?
O1W Cu2 N3 90.33(6) 2 . ?
O1W Cu2 N3 177.52(6) 3 . ?
N3 Cu2 N3 88.74(7) 2 . ?
O1W Cu2 N3 90.33(6) . 3 ?
O1W Cu2 N3 177.51(6) 2 3 ?
O1W Cu2 N3 93.54(6) 3 3 ?
N3 Cu2 N3 88.74(7) 2 3 ?
N3 Cu2 N3 88.74(7) . 3 ?
Cu2 O1W H1W 121(2) . . ?
Cu2 O1W H2W 121(2) . . ?
H1W O1W H2W 106(2) . . ?
C5 N1 N2 108.17(15) . . ?
C5 N1 C1 125.43(16) . . ?
N2 N1 C1 126.28(17) . . ?
N3 N2 N1 107.70(17) . . ?
N2 N3 N4 108.32(15) . . ?
N2 N3 Cu2 125.65(14) . . ?
N4 N3 Cu2 125.88(11) . . ?
C5 N4 N3 106.84(16) . . ?
C5 N4 Cu1 126.62(14) . . ?
N3 N4 Cu1 126.44(11) . . ?
N4 C5 N1 108.97(17) . . ?
N4 C5 H5 125.5 . . ?
N1 C5 H5 125.5 . . ?
N1 C1 C4 106.65(17) . . ?
N1 C1 C3 107.70(16) . . ?
C4 C1 C3 111.5(2) . . ?
N1 C1 C2 107.1(2) . . ?
C4 C1 C2 113.7(3) . . ?
C3 C1 C2 109.8(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
F1 B1 F4 108.99(18) . . ?
F1 B1 F2 109.71(16) . . ?
F4 B1 F2 109.5(2) . . ?
F1 B1 F3 111.1(2) . . ?
F4 B1 F3 107.82(17) . . ?
F2 B1 F3 109.64(19) . . ?

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
C5 N1 N2 N3 -0.6(2) . . . . ?
C1 N1 N2 N3 -176.81(17) . . . . ?
N1 N2 N3 N4 0.27(19) . . . . ?
N1 N2 N3 Cu2 176.08(11) . . . . ?
N2 N3 N4 C5 0.16(18) . . . . ?
Cu2 N3 N4 C5 -175.63(11) . . . . ?
N2 N3 N4 Cu1 176.64(11) . . . . ?
Cu2 N3 N4 Cu1 0.85(19) . . . . ?
N3 N4 C5 N1 -0.54(19) . . . . ?
Cu1 N4 C5 N1 -177.01(11) . . . . ?
N2 N1 C5 N4 0.7(2) . . . . ?
C1 N1 C5 N4 176.96(17) . . . . ?
C5 N1 C1 C4 -76.3(2) . . . . ?
N2 N1 C1 C4 99.3(2) . . . . ?
C5 N1 C1 C3 43.6(3) . . . . ?
N2 N1 C1 C3 -140.86(19) . . . . ?
C5 N1 C1 C2 161.6(2) . . . . ?
N2 N1 C1 C2 -22.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1W F3 0.836(17) 1.879(17) 2.714(2) 176(3) 3_665
O1W H2W F2 0.835(17) 1.867(17) 2.7008(19) 176(3) 15_445
C5 H5 F4 0.95 2.35 3.263(3) 161.4 11_565

_refine_diff_density_max         0.659
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.071

