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

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

data_1b
_database_code_depnum_ccdc_archive 'CCDC 1471287'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H19 B F2 N4'
_chemical_formula_weight         328.17

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   16.6601(5)
_cell_length_b                   17.4301(5)
_cell_length_c                   5.6620(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1644.17(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9403
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      27.04

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6954
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24656
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.383
_diffrn_reflns_theta_max         27.136
_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             1877
_reflns_number_gt                1551
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0369P)²+0.5463P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1877
_refine_ls_number_parameters     126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0771
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
N2 N 0.31528(5) 0.68235(5) 0.91864(16) 0.017(3) Uani 1 1 d . . . . .
N1 N 0.24251(5) 0.68170(5) 1.00980(16) 0.016(3) Uani 1 1 d . . . . .
H9A H 0.4910(14) 0.7500 0.482(4) 0.037(4) Uiso 1 2 d S . P . .
C9 C 0.43596(11) 0.7500 0.5471(3) 0.030(3) Uani 1 2 d S T P . .
H9B H 0.4068(9) 0.7019(9) 0.485(3) 0.037(3) Uiso 1 1 d . . . . .
C7 C 0.35330(9) 0.7500 0.9095(3) 0.0170(3) Uani 1 2 d S T P . .
C8 C 0.43971(9) 0.7500 0.8185(3) 0.0186(3) Uani 1 2 d S T P . .
C2 C 0.14199(7) 0.58762(7) 1.1230(2) 0.0195(3) Uani 1 1 d . . . . .
H2 H 0.1339 0.6144 1.2671 0.023 Uiso 1 1 calc R U . . .
C5 C 0.16458(7) 0.51009(7) 0.6981(2) 0.0236(3) Uani 1 1 d . . . . .
H5 H 0.1719 0.4835 0.5533 0.028 Uiso 1 1 calc R U . . .
C3 C 0.10007(7) 0.52070(7) 1.0759(2) 0.0236(3) Uani 1 1 d . . . . .
H3 H 0.0632 0.5013 1.1891 0.028 Uiso 1 1 calc R U . . .
C1 C 0.19627(6) 0.61495(6) 0.9555(2) 0.0169(2) Uani 1 1 d . . . . .
C6 C 0.20716(6) 0.57710(7) 0.7418(2) 0.0203(3) Uani 1 1 d . . . . .
H6 H 0.2433 0.5968 0.6271 0.024 Uiso 1 1 calc R U . . .
C4 C 0.11141(7) 0.48188(7) 0.8651(2) 0.0254(3) Uani 1 1 d . . . . .
H4 H 0.0827 0.4358 0.8350 0.030 Uiso 1 1 calc R U . . .
B1 B 0.21192(11) 0.7500 1.1610(3) 0.0183(4) Uani 1 2 d S T P . .
F2 F 0.13004(5) 0.7500 1.17706(18) 0.0232(2) Uani 1 2 d S T P . .
F1 F 0.24855(6) 0.7500 1.37919(17) 0.0249(2) Uani 1 2 d S T P . .
C10 C 0.48423(7) 0.67842(7) 0.9037(2) 0.0234(3) Uani 1 1 d . . . . .
H10A H 0.4560 0.6325 0.8486 0.035 Uiso 1 1 calc R U . . .
H10B H 0.4863 0.6783 1.0766 0.035 Uiso 1 1 calc R U . . .
H10C H 0.5390 0.6786 0.8403 0.035 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 N1 1.3177(12) . ?
N2 C7 1.3394(12) . ?
N1 C1 1.4289(14) . ?
N1 B1 1.5523(15) . ?
C9 C8 1.538(2) . ?
C7 N2 1.3394(12) 7_575 ?
C7 C8 1.529(2) . ?
C8 C10 1.5295(15) . ?
C8 C10 1.5295(15) 7_575 ?
C2 C3 1.3854(17) . ?
C2 C1 1.3944(16) . ?
C5 C4 1.3858(18) . ?
C5 C6 1.3888(17) . ?
C3 C4 1.3846(18) . ?
C1 C6 1.3898(16) . ?
B1 F2 1.367(2) . ?
B1 F1 1.378(2) . ?
B1 N1 1.5524(15) 7_575 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N2 C7 117.25(10) . . ?
N2 N1 C1 114.76(9) . . ?
N2 N1 B1 120.76(10) . . ?
C1 N1 B1 124.48(9) . . ?
N2 C7 N2 123.35(14) 7_575 . ?
N2 C7 C8 117.28(7) 7_575 . ?
N2 C7 C8 117.28(7) . . ?
C7 C8 C10 110.51(9) . . ?
C7 C8 C10 110.51(9) . 7_575 ?
C10 C8 C10 109.33(13) . 7_575 ?
C7 C8 C9 107.35(13) . . ?
C10 C8 C9 109.56(9) . . ?
C10 C8 C9 109.56(9) 7_575 . ?
C3 C2 C1 118.91(11) . . ?
C4 C5 C6 120.21(12) . . ?
C4 C3 C2 120.57(11) . . ?
C6 C1 C2 120.97(11) . . ?
C6 C1 N1 120.23(10) . . ?
C2 C1 N1 118.78(10) . . ?
C5 C6 C1 119.19(11) . . ?
C3 C4 C5 120.12(11) . . ?
F2 B1 F1 112.46(14) . . ?
F2 B1 N1 111.37(10) . . ?
F1 B1 N1 110.42(9) . . ?
F2 B1 N1 111.37(10) . 7_575 ?
F1 B1 N1 110.42(9) . 7_575 ?
N1 B1 N1 100.16(12) . 7_575 ?

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 1471288'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 B F7 N4'
_chemical_formula_weight         452.15

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'

_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                   18.5945(8)
_cell_length_b                   7.3570(3)
_cell_length_c                   14.5283(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.9680(10)
_cell_angle_gamma                90
_cell_volume                     1879.55(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9967
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      27.01

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9509
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32581
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.811
_diffrn_reflns_theta_max         27.130
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4156
_reflns_number_gt                3175
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0507P)²+0.9616P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4156
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
F1 F 0.13562(5) 0.65757(15) 0.01746(6) 0.0304(3) Uani 1 1 d . . . . .
F2 F 0.12389(6) 0.39081(15) 0.09311(7) 0.0321(3) Uani 1 1 d . . . . .
F3 F 0.20231(5) 0.40211(14) -0.05281(6) 0.0243(2) Uani 1 1 d . . . . .
F4 F 0.28680(6) 0.45024(14) -0.16965(6) 0.0285(2) Uani 1 1 d . . . . .
F5 F 0.42594(6) 0.61041(16) -0.10006(7) 0.0316(3) Uani 1 1 d . . . . .
F6 F 0.47781(5) 0.73027(15) 0.08674(7) 0.0282(2) Uani 1 1 d . . . . .
F7 F 0.39089(5) 0.70787(14) 0.20043(6) 0.0252(2) Uani 1 1 d . . . . .
N1 N 0.14470(7) 0.6648(2) 0.18712(9) 0.0209(3) Uani 1 1 d . . . . .
N2 N 0.18590(7) 0.6399(2) 0.27741(9) 0.0212(3) Uani 1 1 d . . . . .
N3 N 0.28473(8) 0.50308(19) 0.23036(9) 0.0193(3) Uani 1 1 d . . . . .
N4 N 0.24644(7) 0.53767(19) 0.13755(9) 0.0191(3) Uani 1 1 d . . . . .
C1 C 0.08594(9) 0.7989(2) 0.17041(11) 0.0230(4) Uani 1 1 d . . . . .
C2 C 0.01818(9) 0.7727(3) 0.09441(12) 0.0256(4) Uani 1 1 d . . . . .
H2 H 0.0113 0.6688 0.0536 0.031 Uiso 1 1 calc R U . . .
C3 C -0.03903(10) 0.9010(3) 0.07947(12) 0.0288(4) Uani 1 1 d . . . . .
H3 H -0.0859 0.8841 0.0286 0.035 Uiso 1 1 calc R U . . .
C4 C -0.02840(10) 1.0535(3) 0.13787(13) 0.0304(4) Uani 1 1 d . . . . .
H4 H -0.0678 1.1413 0.1267 0.036 Uiso 1 1 calc R U . . .
C5 C 0.03941(11) 1.0786(3) 0.21261(14) 0.0335(4) Uani 1 1 d . . . . .
H5 H 0.0466 1.1840 0.2523 0.040 Uiso 1 1 calc R U . . .
C6 C 0.09693(10) 0.9506(3) 0.22978(12) 0.0293(4) Uani 1 1 d . . . . .
H6 H 0.1433 0.9668 0.2816 0.035 Uiso 1 1 calc R U . . .
C7 C 0.24995(9) 0.5375(2) 0.29525(11) 0.0188(3) Uani 1 1 d . . . . .
C8 C 0.29105(9) 0.4895(2) 0.39800(11) 0.0178(3) Uani 1 1 d . . . . .
C9 C 0.36673(9) 0.4305(2) 0.42579(11) 0.0204(3) Uani 1 1 d . . . . .
H9 H 0.3920 0.4222 0.3787 0.025 Uiso 1 1 calc R U . . .
C10 C 0.40472(9) 0.3843(2) 0.52152(11) 0.0211(3) Uani 1 1 d . . . . .
H10 H 0.4561 0.3451 0.5393 0.025 Uiso 1 1 calc R U . . .
C11 C 0.36948(9) 0.3938(2) 0.59270(11) 0.0205(3) Uani 1 1 d . . . . .
C12 C 0.29428(9) 0.4527(2) 0.56435(11) 0.0213(4) Uani 1 1 d . . . . .
H12 H 0.2690 0.4600 0.6115 0.026 Uiso 1 1 calc R U . . .
C13 C 0.25551(9) 0.5009(2) 0.46867(11) 0.0206(3) Uani 1 1 d . . . . .
H13 H 0.2044 0.5420 0.4513 0.025 Uiso 1 1 calc R U . . .
C14 C 0.41237(10) 0.3433(3) 0.69666(11) 0.0261(4) Uani 1 1 d . . . . .
H14A H 0.4470 0.2424 0.6977 0.039 Uiso 1 1 calc R U . . .
H14B H 0.3763 0.3064 0.7295 0.039 Uiso 1 1 calc R U . . .
H14C H 0.4417 0.4484 0.7303 0.039 Uiso 1 1 calc R U . . .
C15 C 0.29322(9) 0.5528(2) 0.07804(11) 0.0189(3) Uani 1 1 d . . . . .
C16 C 0.26861(9) 0.4895(2) -0.01772(11) 0.0205(4) Uani 1 1 d . . . . .
C17 C 0.31238(10) 0.5114(2) -0.07746(11) 0.0221(4) Uani 1 1 d . . . . .
C18 C 0.38294(10) 0.5908(2) -0.04247(12) 0.0231(4) Uani 1 1 d . . . . .
C19 C 0.40942(9) 0.6511(2) 0.05249(12) 0.0218(4) Uani 1 1 d . . . . .
C20 C 0.36456(9) 0.6348(2) 0.11129(11) 0.0208(3) Uani 1 1 d . . . . .
B1 B 0.15877(11) 0.5564(3) 0.10087(13) 0.0232(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
F1 B1 1.367(2) . ?
F2 B1 1.368(2) . ?
F3 C16 1.3360(19) . ?
F4 C17 1.3449(18) . ?
F5 C18 1.3398(18) . ?
F6 C19 1.3389(19) . ?
F7 C20 1.3394(18) . ?
N1 N2 1.2993(18) . ?
N1 C1 1.433(2) . ?
N1 B1 1.577(2) . ?
N2 C7 1.361(2) . ?
N3 N4 1.3289(17) . ?
N3 C7 1.329(2) . ?
N4 C15 1.4160(19) . ?
N4 B1 1.548(2) . ?
C1 C6 1.385(3) . ?
C1 C2 1.393(2) . ?
C2 C3 1.386(2) . ?
C3 C4 1.381(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.385(3) . ?
C7 C8 1.482(2) . ?
C8 C13 1.393(2) . ?
C8 C9 1.401(2) . ?
C9 C10 1.382(2) . ?
C10 C11 1.394(2) . ?
C11 C12 1.392(2) . ?
C11 C14 1.507(2) . ?
C12 C13 1.388(2) . ?
C15 C20 1.393(2) . ?
C15 C16 1.396(2) . ?
C16 C17 1.379(2) . ?
C17 C18 1.374(2) . ?
C18 C19 1.379(2) . ?
C19 C20 1.380(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 115.81(13) . . ?
N2 N1 B1 122.33(13) . . ?
C1 N1 B1 121.85(13) . . ?
N1 N2 C7 117.57(13) . . ?
N4 N3 C7 117.35(13) . . ?
N3 N4 C15 113.69(12) . . ?
N3 N4 B1 121.56(12) . . ?
C15 N4 B1 124.75(12) . . ?
C6 C1 C2 121.20(16) . . ?
C6 C1 N1 119.96(15) . . ?
C2 C1 N1 118.84(16) . . ?
C3 C2 C1 118.70(17) . . ?
C4 C3 C2 120.52(16) . . ?
C3 C4 C5 120.17(17) . . ?
C4 C5 C6 120.28(18) . . ?
C1 C6 C5 119.12(16) . . ?
N3 C7 N2 124.59(14) . . ?
N3 C7 C8 117.29(14) . . ?
N2 C7 C8 117.17(13) . . ?
C13 C8 C9 118.63(14) . . ?
C13 C8 C7 121.03(14) . . ?
C9 C8 C7 120.34(13) . . ?
C10 C9 C8 120.22(14) . . ?
C9 C10 C11 121.62(15) . . ?
C12 C11 C10 117.72(14) . . ?
C12 C11 C14 121.77(14) . . ?
C10 C11 C14 120.50(15) . . ?
C13 C12 C11 121.38(15) . . ?
C12 C13 C8 120.43(15) . . ?
C20 C15 C16 117.18(14) . . ?
C20 C15 N4 121.81(14) . . ?
C16 C15 N4 120.99(14) . . ?
F3 C16 C17 118.45(14) . . ?
F3 C16 C15 120.26(14) . . ?
C17 C16 C15 121.28(15) . . ?
F4 C17 C18 119.79(14) . . ?
F4 C17 C16 119.86(15) . . ?
C18 C17 C16 120.33(15) . . ?
F5 C18 C17 120.45(14) . . ?
F5 C18 C19 119.91(15) . . ?
C17 C18 C19 119.64(14) . . ?
F6 C19 C18 119.94(14) . . ?
F6 C19 C20 120.01(14) . . ?
C18 C19 C20 120.03(15) . . ?
F7 C20 C19 117.33(15) . . ?
F7 C20 C15 121.12(14) . . ?
C19 C20 C15 121.49(15) . . ?
F1 B1 F2 114.06(14) . . ?
F1 B1 N4 110.29(14) . . ?
F2 B1 N4 111.54(15) . . ?
F1 B1 N1 110.07(15) . . ?
F2 B1 N1 108.62(14) . . ?
N4 B1 N1 101.52(12) . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_Na-1c
_database_code_depnum_ccdc_archive 'CCDC 1471289'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-10 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         ?
_chemical_formula_sum            'C33 H43 B F2 N4 Na O5'
_chemical_formula_weight         647.51

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.0275(9)
_cell_length_b                   12.8604(9)
_cell_length_c                   23.3615(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.306(2)
_cell_angle_gamma                90
_cell_volume                     3307.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9745
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      26.87

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             1372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6742
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            62330
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.934
_diffrn_reflns_theta_max         26.371
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             12845
_reflns_number_gt                11185
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²+1.1969P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.5(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         12845
_refine_ls_number_parameters     932
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
F1_1 F 0.08818(14) 0.08107(13) 0.33419(6) 0.0196(4) Uani 1 1 d . . . . .
F2_1 F 0.06708(14) 0.01405(13) 0.42131(6) 0.0181(4) Uani 1 1 d . . . . .
N1_1 N 0.1257(2) -0.1041(2) 0.34564(9) 0.0167(5) Uani 1 1 d . . . . .
N2_1 N 0.2198(2) -0.1469(2) 0.31743(10) 0.0187(5) Uani 1 1 d . . . . .
N3_1 N 0.3594(2) -0.0174(2) 0.35703(9) 0.0161(5) Uani 1 1 d . . . . .
N4_1 N 0.2695(2) 0.02147(19) 0.38901(9) 0.0143(5) Uani 1 1 d . . . . .
C1_1 C 0.0170(3) -0.1620(2) 0.33887(11) 0.0180(6) Uani 1 1 d . . . . .
C2_1 C -0.0944(3) -0.1150(3) 0.34695(12) 0.0200(7) Uani 1 1 d . . . . .
H2_1 H -0.0974 -0.0430 0.3559 0.024 Uiso 1 1 calc R U . . .
C3_1 C -0.2007(3) -0.1722(3) 0.34213(12) 0.0221(7) Uani 1 1 d . . . . .
H3_1 H -0.2760 -0.1391 0.3480 0.027 Uiso 1 1 calc R U . . .
C4_1 C -0.1987(3) -0.2771(3) 0.32879(12) 0.0258(7) Uani 1 1 d . . . . .
H4_1 H -0.2718 -0.3164 0.3257 0.031 Uiso 1 1 calc R U . . .
C5_1 C -0.0884(3) -0.3235(3) 0.32013(13) 0.0255(7) Uani 1 1 d . . . . .
H5_1 H -0.0861 -0.3953 0.3107 0.031 Uiso 1 1 calc R U . . .
C6_1 C 0.0190(3) -0.2676(3) 0.32485(12) 0.0235(7) Uani 1 1 d . . . . .
H6_1 H 0.0939 -0.3010 0.3186 0.028 Uiso 1 1 calc R U . . .
C7_1 C 0.3262(2) -0.0970(2) 0.32281(11) 0.0163(6) Uani 1 1 d . . . . .
C8_1 C 0.4213(3) -0.1359(2) 0.28575(11) 0.0188(7) Uani 1 1 d . . . . .
C9_1 C 0.4187(3) -0.2370(3) 0.26466(12) 0.0234(7) Uani 1 1 d . . . . .
H9_1 H 0.3551 -0.2825 0.2742 0.028 Uiso 1 1 calc R U . . .
C10_1 C 0.5079(3) -0.2721(3) 0.22984(13) 0.0280(8) Uani 1 1 d . . . . .
H10_1 H 0.5056 -0.3421 0.2168 0.034 Uiso 1 1 calc R U . . .
C11_1 C 0.6002(3) -0.2072(3) 0.21365(12) 0.0270(8) Uani 1 1 d . . . . .
C12_1 C 0.6014(3) -0.1063(3) 0.23395(13) 0.0272(8) Uani 1 1 d . . . . .
H12_1 H 0.6637 -0.0601 0.2235 0.033 Uiso 1 1 calc R U . . .
C13_1 C 0.5131(3) -0.0711(3) 0.26934(12) 0.0228(7) Uani 1 1 d . . . . .
H13_1 H 0.5157 -0.0012 0.2825 0.027 Uiso 1 1 calc R U . . .
C14_1 C 0.6989(3) -0.2459(3) 0.17683(15) 0.0410(10) Uani 1 1 d . . . . .
H14A_1 H 0.7780 -0.2215 0.1927 0.061 Uiso 1 1 calc R U . . .
H14B_1 H 0.6846 -0.2193 0.1377 0.061 Uiso 1 1 calc R U . . .
H14C_1 H 0.6982 -0.3221 0.1762 0.061 Uiso 1 1 calc R U . . .
C15_1 C 0.3149(2) 0.0990(2) 0.42935(11) 0.0145(6) Uani 1 1 d . . . . .
C16_1 C 0.3149(2) 0.0788(2) 0.48835(11) 0.0169(6) Uani 1 1 d . . . . .
C17_1 C 0.3662(3) 0.1525(2) 0.52620(12) 0.0200(7) Uani 1 1 d . . . . .
H17_1 H 0.3653 0.1398 0.5662 0.024 Uiso 1 1 calc R U . . .
C18_1 C 0.4184(2) 0.2436(2) 0.50766(12) 0.0194(7) Uani 1 1 d . . . . .
C19_1 C 0.4150(2) 0.2617(2) 0.44882(12) 0.0187(6) Uani 1 1 d . . . . .
H19_1 H 0.4495 0.3240 0.4352 0.022 Uiso 1 1 calc R U . . .
C20_1 C 0.3627(2) 0.1915(2) 0.40940(12) 0.0174(6) Uani 1 1 d . . . . .
C21_1 C 0.2642(3) -0.0209(3) 0.51148(12) 0.0253(7) Uani 1 1 d . . . . .
H21A_1 H 0.3151 -0.0439 0.5449 0.038 Uiso 1 1 calc R U . . .
H21B_1 H 0.2634 -0.0747 0.4817 0.038 Uiso 1 1 calc R U . . .
H21C_1 H 0.1812 -0.0089 0.5229 0.038 Uiso 1 1 calc R U . . .
C22_1 C 0.4798(3) 0.3182(3) 0.55016(13) 0.0256(7) Uani 1 1 d . . . . .
H22A_1 H 0.4857 0.3869 0.5325 0.038 Uiso 1 1 calc R U . . .
H22B_1 H 0.5615 0.2926 0.5614 0.038 Uiso 1 1 calc R U . . .
H22C_1 H 0.4321 0.3233 0.5842 0.038 Uiso 1 1 calc R U . . .
C23_1 C 0.3596(3) 0.2164(3) 0.34603(11) 0.0206(7) Uani 1 1 d . . . . .
H23A_1 H 0.3797 0.2899 0.3408 0.031 Uiso 1 1 calc R U . . .
H23B_1 H 0.2782 0.2024 0.3287 0.031 Uiso 1 1 calc R U . . .
H23C_1 H 0.4190 0.1729 0.3275 0.031 Uiso 1 1 calc R U . . .
B1_1 B 0.1366(3) 0.0029(3) 0.37314(13) 0.0161(7) Uani 1 1 d . . . . .
F1_2 F 0.92222(16) 0.34098(15) 0.06005(8) 0.0307(5) Uani 1 1 d . . . . .
F2_2 F 0.91672(16) 0.24495(15) 0.14073(10) 0.0385(5) Uani 1 1 d . . . . .
N1_2 N 0.8847(2) 0.42911(19) 0.14928(9) 0.0166(5) Uani 1 1 d . . . . .
N2_2 N 0.8011(2) 0.4563(2) 0.18784(10) 0.0185(5) Uani 1 1 d . . . . .
N3_2 N 0.6489(2) 0.3457(2) 0.14074(9) 0.0156(5) Uani 1 1 d . . . . .
N4_2 N 0.7284(2) 0.32132(19) 0.10021(9) 0.0165(5) Uani 1 1 d . . . . .
C1_2 C 0.9923(3) 0.4869(3) 0.15517(11) 0.0196(7) Uani 1 1 d . . . . .
C2_2 C 0.9956(3) 0.5833(3) 0.18247(13) 0.0294(8) Uani 1 1 d . . . . .
H2_2 H 0.9242 0.6098 0.1981 0.035 Uiso 1 1 calc R U . . .
C3_2 C 1.1022(3) 0.6409(3) 0.18699(14) 0.0411(10) Uani 1 1 d . . . . .
H3_2 H 1.1031 0.7062 0.2061 0.049 Uiso 1 1 calc R U . . .
C4_2 C 1.2069(3) 0.6046(3) 0.16406(13) 0.0358(9) Uani 1 1 d . . . . .
H4_2 H 1.2791 0.6451 0.1663 0.043 Uiso 1 1 calc R U . . .
C5_2 C 1.2043(3) 0.5089(3) 0.13801(13) 0.0300(8) Uani 1 1 d . . . . .
H5_2 H 1.2761 0.4826 0.1227 0.036 Uiso 1 1 calc R U . . .
C6_2 C 1.0995(3) 0.4501(3) 0.13371(13) 0.0249(7) Uani 1 1 d . . . . .
H6_2 H 1.1004 0.3837 0.1159 0.030 Uiso 1 1 calc R U . . .
C7_2 C 0.6933(2) 0.4087(2) 0.18235(11) 0.0153(6) Uani 1 1 d . . . . .
C8_2 C 0.6101(3) 0.4354(2) 0.22809(11) 0.0154(6) Uani 1 1 d . . . . .
C9_2 C 0.4843(3) 0.4336(2) 0.21868(12) 0.0191(7) Uani 1 1 d . . . . .
H9_2 H 0.4495 0.4114 0.1826 0.023 Uiso 1 1 calc R U . . .
C10_2 C 0.4092(3) 0.4639(2) 0.26126(12) 0.0193(7) Uani 1 1 d . . . . .
H10_2 H 0.3236 0.4630 0.2536 0.023 Uiso 1 1 calc R U . . .
C11_2 C 0.4564(3) 0.4954(2) 0.31487(12) 0.0198(7) Uani 1 1 d . . . . .
C12_2 C 0.5819(3) 0.4929(3) 0.32478(12) 0.0221(7) Uani 1 1 d . . . . .
H12_2 H 0.6163 0.5116 0.3616 0.026 Uiso 1 1 calc R U . . .
C13_2 C 0.6577(3) 0.4640(2) 0.28256(12) 0.0196(7) Uani 1 1 d . . . . .
H13_2 H 0.7431 0.4635 0.2906 0.024 Uiso 1 1 calc R U . . .
C14_2 C 0.3750(3) 0.5328(3) 0.36056(13) 0.0304(8) Uani 1 1 d . . . . .
H14A_2 H 0.4173 0.5864 0.3839 0.046 Uiso 1 1 calc R U . . .
H14B_2 H 0.3546 0.4742 0.3851 0.046 Uiso 1 1 calc R U . . .
H14C_2 H 0.3003 0.5620 0.3423 0.046 Uiso 1 1 calc R U . . .
C15_2 C 0.6752(2) 0.2558(2) 0.05581(12) 0.0171(6) Uani 1 1 d . . . . .
C16_2 C 0.6603(3) 0.2932(2) -0.00053(12) 0.0215(7) Uani 1 1 d . . . . .
C17_2 C 0.6042(3) 0.2285(3) -0.04225(12) 0.0255(7) Uani 1 1 d . . . . .
H17_2 H 0.5931 0.2539 -0.0804 0.031 Uiso 1 1 calc R U . . .
C18_2 C 0.5643(3) 0.1294(3) -0.03046(12) 0.0231(7) Uani 1 1 d . . . . .
C19_2 C 0.5837(3) 0.0937(2) 0.02555(13) 0.0217(7) Uani 1 1 d . . . . .
H19_2 H 0.5583 0.0253 0.0345 0.026 Uiso 1 1 calc R U . . .
C20_2 C 0.6388(2) 0.1542(2) 0.06885(12) 0.0182(6) Uani 1 1 d . . . . .
C21_2 C 0.7016(3) 0.4000(3) -0.01694(14) 0.0313(8) Uani 1 1 d . . . . .
H21A_2 H 0.6447 0.4286 -0.0466 0.047 Uiso 1 1 calc R U . . .
H21B_2 H 0.7828 0.3956 -0.0317 0.047 Uiso 1 1 calc R U . . .
H21C_2 H 0.7041 0.4453 0.0168 0.047 Uiso 1 1 calc R U . . .
C22_2 C 0.4998(3) 0.0632(3) -0.07589(13) 0.0301(8) Uani 1 1 d . . . . .
H22A_2 H 0.5213 -0.0100 -0.0694 0.045 Uiso 1 1 calc R U . . .
H22B_2 H 0.5244 0.0846 -0.1138 0.045 Uiso 1 1 calc R U . . .
H22C_2 H 0.4118 0.0718 -0.0741 0.045 Uiso 1 1 calc R U . . .
C23_2 C 0.6584(3) 0.1104(3) 0.12848(13) 0.0251(7) Uani 1 1 d . . . . .
H23A_2 H 0.6354 0.0368 0.1283 0.038 Uiso 1 1 calc R U . . .
H23B_2 H 0.6084 0.1487 0.1547 0.038 Uiso 1 1 calc R U . . .
H23C_2 H 0.7443 0.1172 0.1413 0.038 Uiso 1 1 calc R U . . .
B1_2 B 0.8644(3) 0.3340(3) 0.11123(15) 0.0201(7) Uani 1 1 d . . . . .
Na1_3 Na -0.04280(10) 0.17105(9) 0.39494(4) 0.0181(2) Uani 1 1 d . . . . .
O1_3 O -0.03713(18) 0.28147(17) 0.47477(8) 0.0230(5) Uani 1 1 d . . . . .
O2_3 O -0.17346(18) 0.10029(16) 0.47208(8) 0.0214(5) Uani 1 1 d . . . . .
O3_3 O -0.24482(18) 0.11821(17) 0.35589(8) 0.0230(5) Uani 1 1 d . . . . .
O4_3 O -0.10214(18) 0.26860(18) 0.30996(9) 0.0257(5) Uani 1 1 d . . . . .
O5_3 O 0.08682(18) 0.32715(18) 0.38131(8) 0.0240(5) Uani 1 1 d . . . . .
C24_3 C -0.0758(3) 0.2345(3) 0.52568(13) 0.0295(8) Uani 1 1 d . . . . .
H24A_3 H -0.0851 0.2881 0.5556 0.035 Uiso 1 1 calc R U . . .
H24B_3 H -0.0147 0.1832 0.5404 0.035 Uiso 1 1 calc R U . . .
C25_3 C -0.1943(3) 0.1820(3) 0.51190(13) 0.0265(7) Uani 1 1 d . . . . .
H25A_3 H -0.2268 0.1531 0.5472 0.032 Uiso 1 1 calc R U . . .
H25B_3 H -0.2539 0.2323 0.4948 0.032 Uiso 1 1 calc R U . . .
C26_3 C -0.2822(3) 0.0535(3) 0.44826(13) 0.0261(7) Uani 1 1 d . . . . .
H26A_3 H -0.3426 0.0508 0.4780 0.031 Uiso 1 1 calc R U . . .
H26B_3 H -0.2644 -0.0189 0.4369 0.031 Uiso 1 1 calc R U . . .
C27_3 C -0.3361(3) 0.1116(3) 0.39667(14) 0.0271(7) Uani 1 1 d . . . . .
H27A_3 H -0.4082 0.0742 0.3799 0.033 Uiso 1 1 calc R U . . .
H27B_3 H -0.3616 0.1822 0.4080 0.033 Uiso 1 1 calc R U . . .
C28_3 C -0.2852(3) 0.1753(3) 0.30564(13) 0.0299(8) Uani 1 1 d . . . . .
H28A_3 H -0.3272 0.2397 0.3165 0.036 Uiso 1 1 calc R U . . .
H28B_3 H -0.3424 0.1327 0.2813 0.036 Uiso 1 1 calc R U . . .
C29_3 C -0.1746(3) 0.2014(3) 0.27362(13) 0.0291(8) Uani 1 1 d . . . . .
H29A_3 H -0.1290 0.1374 0.2651 0.035 Uiso 1 1 calc R U . . .
H29B_3 H -0.1984 0.2366 0.2370 0.035 Uiso 1 1 calc R U . . .
C30_3 C 0.0064(3) 0.3036(3) 0.28551(13) 0.0294(8) Uani 1 1 d . . . . .
H30A_3 H -0.0129 0.3382 0.2482 0.035 Uiso 1 1 calc R U . . .
H30B_3 H 0.0615 0.2444 0.2794 0.035 Uiso 1 1 calc R U . . .
C31_3 C 0.0640(3) 0.3786(3) 0.32760(14) 0.0314(8) Uani 1 1 d . . . . .
H31A_3 H 0.1413 0.4047 0.3134 0.038 Uiso 1 1 calc R U . . .
H31B_3 H 0.0094 0.4387 0.3324 0.038 Uiso 1 1 calc R U . . .
C32_3 C 0.0936(3) 0.3954(3) 0.42964(14) 0.0317(8) Uani 1 1 d . . . . .
H32A_3 H 0.0292 0.4489 0.4254 0.038 Uiso 1 1 calc R U . . .
H32B_3 H 0.1734 0.4310 0.4325 0.038 Uiso 1 1 calc R U . . .
C33_3 C 0.0777(3) 0.3326(3) 0.48219(13) 0.0286(8) Uani 1 1 d . . . . .
H33A_3 H 0.1439 0.2808 0.4875 0.034 Uiso 1 1 calc R U . . .
H33B_3 H 0.0795 0.3782 0.5164 0.034 Uiso 1 1 calc R U . . .
O1_4 O 1.19896(19) 0.14516(18) 0.18740(8) 0.0267(5) Uani 1 1 d . . . . .
Na1A_4 Na 1.0742(3) 0.1879(2) 0.10108(12) 0.0169(5) Uani 0.485(2) 1 d . . P A 1
C1A_4 C 0.9504(9) -0.0366(8) 0.1056(5) 0.049(3) Uani 0.485(2) 1 d . . P A 1
H1A_4 H 0.8853 -0.0052 0.1274 0.059 Uiso 0.485(2) 1 calc R U P A 1
H1B_4 H 0.9479 -0.1130 0.1108 0.059 Uiso 0.485(2) 1 calc R U P A 1
O2A_4 O 1.0645(7) 0.0024(5) 0.1257(3) 0.0366(17) Uani 0.485(2) 1 d . . P A 1
C2A_4 C 0.9317(11) -0.0098(10) 0.0428(7) 0.049(4) Uani 0.485(2) 1 d . . P A 1
H2A_4 H 0.9970 -0.0407 0.0210 0.059 Uiso 0.485(2) 1 calc R U P A 1
H2B_4 H 0.8527 -0.0372 0.0272 0.059 Uiso 0.485(2) 1 calc R U P A 1
O3A_4 O 0.9340(4) 0.0999(4) 0.0384(3) 0.0390(14) Uani 0.485(2) 1 d . . P A 1
O5A_4 O 1.2826(5) 0.2690(4) 0.0978(2) 0.0256(11) Uani 0.485(2) 1 d . . P A 1
O4A_4 O 1.1414(14) 0.2023(11) 0.0041(5) 0.023(2) Uani 0.485(2) 1 d . . P A 1
C4A_4 C 1.0756(7) 0.1366(6) -0.0346(3) 0.035(2) Uani 0.485(2) 1 d . . P A 1
H4A_4 H 1.1082 0.0650 -0.0317 0.042 Uiso 0.485(2) 1 calc R U P A 1
H4B_4 H 1.0826 0.1615 -0.0744 0.042 Uiso 0.485(2) 1 calc R U P A 1
C10A_4 C 1.0898(11) -0.0067(8) 0.1866(5) 0.045(2) Uani 0.485(2) 1 d . . P A 1
H10A_4 H 1.0903 -0.0810 0.1978 0.054 Uiso 0.485(2) 1 calc R U P A 1
H10B_4 H 1.0256 0.0290 0.2071 0.054 Uiso 0.485(2) 1 calc R U P A 1
C5A_4 C 1.2687(16) 0.2005(13) 0.0019(5) 0.030(3) Uani 0.485(2) 1 d . . P A 1
H5A_4 H 1.2919 0.2139 -0.0377 0.036 Uiso 0.485(2) 1 calc R U P A 1
H5B_4 H 1.3005 0.1315 0.0140 0.036 Uiso 0.485(2) 1 calc R U P A 1
C9A_4 C 1.2065(13) 0.0395(14) 0.2022(7) 0.045(2) Uani 0.485(2) 1 d . . P A 1
H9A_4 H 1.2259 0.0317 0.2439 0.054 Uiso 0.485(2) 1 calc R U P A 1
H9B_4 H 1.2710 0.0050 0.1814 0.054 Uiso 0.485(2) 1 calc R U P A 1
C8A_4 C 1.3019(9) 0.2130(9) 0.1782(3) 0.0267(5) Uani 0.485(2) 1 d . . P A 1
H8A_4 H 1.2717 0.2851 0.1814 0.032 Uiso 0.485(2) 1 calc R U P A 1
H8B_4 H 1.3608 0.2020 0.2112 0.032 Uiso 0.485(2) 1 calc R U P A 1
C7A_4 C 1.3613(9) 0.2106(8) 0.1346(3) 0.0256(11) Uani 0.485(2) 1 d . . P A 1
H7A_4 H 1.3720 0.1388 0.1205 0.031 Uiso 0.485(2) 1 calc R U P A 1
H7B_4 H 1.4417 0.2443 0.1411 0.031 Uiso 0.485(2) 1 calc R U P A 1
C6A_4 C 1.3206(6) 0.2828(5) 0.0413(3) 0.0193(14) Uani 0.485(2) 1 d . . P A 1
H6A_4 H 1.4104 0.2803 0.0419 0.023 Uiso 0.485(2) 1 calc R U P A 1
H6B_4 H 1.2941 0.3520 0.0269 0.023 Uiso 0.485(2) 1 calc R U P A 1
C3A_4 C 0.947(3) 0.138(3) -0.0198(10) 0.039(7) Uani 0.485(2) 1 d . . P A 1
H3A_4 H 0.9154 0.2098 -0.0231 0.046 Uiso 0.485(2) 1 calc R U P A 1
H3B_4 H 0.8986 0.0938 -0.0473 0.046 Uiso 0.485(2) 1 calc R U P A 1
C10B_4 C 1.1272(7) -0.0279(7) 0.2053(3) 0.0287(18) Uani 0.515(2) 1 d . . P A 2
H10C_4 H 1.1514 -0.0980 0.2193 0.034 Uiso 0.515(2) 1 calc R U P A 2
H10D_4 H 1.0684 0.0016 0.2314 0.034 Uiso 0.515(2) 1 calc R U P A 2
C9B_4 C 1.2388(9) 0.0429(12) 0.2030(6) 0.0287(18) Uani 0.515(2) 1 d . . P A 2
H9C_4 H 1.2837 0.0444 0.2410 0.034 Uiso 0.515(2) 1 calc R U P A 2
H9D_4 H 1.2939 0.0160 0.1745 0.034 Uiso 0.515(2) 1 calc R U P A 2
C4B_4 C 0.956(2) 0.126(2) -0.0174(7) 0.027(5) Uani 0.515(2) 1 d . . P A 2
H4C_4 H 0.9529 0.1310 -0.0597 0.032 Uiso 0.515(2) 1 calc R U P A 2
H4D_4 H 0.9113 0.1852 -0.0021 0.032 Uiso 0.515(2) 1 calc R U P A 2
C8B_4 C 1.3058(9) 0.2025(8) 0.1912(3) 0.0267(5) Uani 0.515(2) 1 d . . P A 2
H8C_4 H 1.3693 0.1678 0.2161 0.032 Uiso 0.515(2) 1 calc R U P A 2
H8D_4 H 1.2922 0.2736 0.2057 0.032 Uiso 0.515(2) 1 calc R U P A 2
C7B_4 C 1.3442(8) 0.2038(8) 0.1184(3) 0.0216(10) Uani 0.515(2) 1 d . . P A 2
H7C_4 H 1.4074 0.2572 0.1132 0.026 Uiso 0.515(2) 1 calc R U P A 2
H7D_4 H 1.3785 0.1354 0.1085 0.026 Uiso 0.515(2) 1 calc R U P A 2
Na1B_4 Na 1.0611(2) 0.1329(2) 0.10548(11) 0.0169(5) Uani 0.515(2) 1 d . . P A 2
C1B_4 C 0.9596(6) -0.0818(5) 0.1450(3) 0.0258(15) Uani 0.515(2) 1 d . . P A 2
H1C_4 H 0.9020 -0.0420 0.1675 0.031 Uiso 0.515(2) 1 calc R U P A 2
H1D_4 H 0.9656 -0.1532 0.1606 0.031 Uiso 0.515(2) 1 calc R U P A 2
O3B_4 O 0.9128(5) 0.0187(5) 0.0616(2) 0.0207(13) Uani 0.515(2) 1 d . . P A 2
C3B_4 C 0.9013(6) 0.0249(5) 0.0006(3) 0.0218(14) Uani 0.515(2) 1 d . . P A 2
H3C_4 H 0.8145 0.0221 -0.0128 0.026 Uiso 0.515(2) 1 calc R U P A 2
H3D_4 H 0.9438 -0.0343 -0.0164 0.026 Uiso 0.515(2) 1 calc R U P A 2
O2B_4 O 1.0750(5) -0.0336(5) 0.1488(3) 0.0255(14) Uani 0.515(2) 1 d . . P A 2
C2B_4 C 0.9148(6) -0.0848(6) 0.0824(3) 0.0257(15) Uani 0.515(2) 1 d . . P A 2
H2C_4 H 0.9697 -0.1280 0.0602 0.031 Uiso 0.515(2) 1 calc R U P A 2
H2D_4 H 0.8323 -0.1153 0.0785 0.031 Uiso 0.515(2) 1 calc R U P A 2
O5B_4 O 1.2408(4) 0.2256(4) 0.08035(19) 0.0216(10) Uani 0.515(2) 1 d . . P A 2
O4B_4 O 1.0797(4) 0.1278(4) 0.0049(2) 0.0210(10) Uani 0.515(2) 1 d . . P A 2
C5B_4 C 1.148(2) 0.217(2) -0.0122(7) 0.030(4) Uani 0.515(2) 1 d . . P A 2
H5C_4 H 1.1039 0.2819 -0.0045 0.036 Uiso 0.515(2) 1 calc R U P A 2
H5D_4 H 1.1618 0.2138 -0.0537 0.036 Uiso 0.515(2) 1 calc R U P A 2
C6B_4 C 1.2658(15) 0.2145(12) 0.0217(4) 0.026(3) Uani 0.515(2) 1 d . . P A 2
H6C_4 H 1.3080 0.1478 0.0156 0.032 Uiso 0.515(2) 1 calc R U P A 2
H6D_4 H 1.3187 0.2720 0.0099 0.032 Uiso 0.515(2) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1_1 B1_1 1.438(4) . ?
F1_1 Na1_3 2.3824(19) . ?
F2_1 B1_1 1.405(3) . ?
F2_1 Na1_3 2.416(2) . ?
N1_1 N2_1 1.376(3) . ?
N1_1 C1_1 1.412(4) . ?
N1_1 B1_1 1.520(4) . ?
N2_1 C7_1 1.337(4) . ?
N3_1 C7_1 1.337(4) . ?
N3_1 N4_1 1.370(3) . ?
N4_1 C15_1 1.442(4) . ?
N4_1 B1_1 1.510(4) . ?
C1_1 C2_1 1.391(4) . ?
C1_1 C6_1 1.398(4) . ?
C2_1 C3_1 1.383(4) . ?
C3_1 C4_1 1.386(5) . ?
C4_1 C5_1 1.380(4) . ?
C5_1 C6_1 1.384(4) . ?
C7_1 C8_1 1.485(4) . ?
C8_1 C13_1 1.382(4) . ?
C8_1 C9_1 1.389(4) . ?
C9_1 C10_1 1.388(4) . ?
C10_1 C11_1 1.386(5) . ?
C11_1 C12_1 1.382(5) . ?
C11_1 C14_1 1.510(4) . ?
C12_1 C13_1 1.389(4) . ?
C15_1 C20_1 1.393(4) . ?
C15_1 C16_1 1.403(4) . ?
C16_1 C17_1 1.393(4) . ?
C16_1 C21_1 1.512(4) . ?
C17_1 C18_1 1.386(4) . ?
C18_1 C19_1 1.392(4) . ?
C18_1 C22_1 1.512(4) . ?
C19_1 C20_1 1.391(4) . ?
C20_1 C23_1 1.513(4) . ?
B1_1 Na1_3 2.994(3) . ?
F1_2 B1_2 1.390(4) . ?
F1_2 Na1A_4 2.724(4) . ?
F2_2 B1_2 1.440(4) . ?
F2_2 Na1A_4 2.144(3) . ?
F2_2 Na1B_4 2.332(3) . ?
N1_2 N2_2 1.370(3) . ?
N1_2 C1_2 1.401(4) . ?
N1_2 B1_2 1.521(4) . ?
N2_2 C7_2 1.336(4) . ?
N3_2 C7_2 1.337(4) . ?
N3_2 N4_2 1.364(3) . ?
N4_2 C15_2 1.436(4) . ?
N4_2 B1_2 1.516(4) . ?
C1_2 C6_2 1.393(4) . ?
C1_2 C2_2 1.394(5) . ?
C2_2 C3_2 1.388(5) . ?
C3_2 C4_2 1.382(5) . ?
C4_2 C5_2 1.373(5) . ?
C5_2 C6_2 1.380(5) . ?
C7_2 C8_2 1.488(4) . ?
C8_2 C9_2 1.391(4) . ?
C8_2 C13_2 1.398(4) . ?
C9_2 C10_2 1.387(4) . ?
C10_2 C11_2 1.389(4) . ?
C11_2 C12_2 1.390(4) . ?
C11_2 C14_2 1.512(4) . ?
C12_2 C13_2 1.380(4) . ?
C15_2 C16_2 1.402(4) . ?
C15_2 C20_2 1.405(4) . ?
C16_2 C17_2 1.398(4) . ?
C16_2 C21_2 1.504(5) . ?
C17_2 C18_2 1.382(5) . ?
C18_2 C19_2 1.392(4) . ?
C18_2 C22_2 1.507(4) . ?
C19_2 C20_2 1.388(4) . ?
C20_2 C23_2 1.507(4) . ?
B1_2 Na1A_4 3.001(4) . ?
Na1_3 O1_3 2.342(2) . ?
Na1_3 O4_3 2.407(2) . ?
Na1_3 O3_3 2.454(2) . ?
Na1_3 O5_3 2.495(2) . ?
Na1_3 O2_3 2.540(2) . ?
O1_3 C24_3 1.421(4) . ?
O1_3 C33_3 1.429(4) . ?
O2_3 C26_3 1.426(4) . ?
O2_3 C25_3 1.430(4) . ?
O3_3 C27_3 1.428(4) . ?
O3_3 C28_3 1.433(4) . ?
O4_3 C29_3 1.424(4) . ?
O4_3 C30_3 1.428(4) . ?
O5_3 C31_3 1.428(4) . ?
O5_3 C32_3 1.429(4) . ?
C24_3 C25_3 1.490(5) . ?
C26_3 C27_3 1.511(5) . ?
C28_3 C29_3 1.505(4) . ?
C30_3 C31_3 1.493(5) . ?
C32_3 C33_3 1.488(5) . ?
O1_4 C8B_4 1.389(10) . ?
O1_4 C9A_4 1.404(18) . ?
O1_4 C9B_4 1.428(16) . ?
O1_4 C8A_4 1.457(10) . ?
O1_4 Na1B_4 2.380(3) . ?
O1_4 Na1A_4 2.438(3) . ?
Na1A_4 O3A_4 2.356(5) . ?
Na1A_4 O4A_4 2.432(10) . ?
Na1A_4 O2A_4 2.457(8) . ?
Na1A_4 O5A_4 2.529(6) . ?
Na1A_4 C8A_4 3.022(10) . ?
C1A_4 O2A_4 1.410(13) . ?
C1A_4 C2A_4 1.509(18) . ?
O2A_4 C10A_4 1.439(12) . ?
C2A_4 O3A_4 1.415(14) . ?
O3A_4 C3A_4 1.46(2) . ?
O5A_4 C7A_4 1.404(10) . ?
O5A_4 C6A_4 1.419(7) . ?
O4A_4 C5A_4 1.41(2) . ?
O4A_4 C4A_4 1.407(18) . ?
C4A_4 C3A_4 1.48(3) . ?
C10A_4 C9A_4 1.445(17) . ?
C5A_4 C6A_4 1.494(16) . ?
C8A_4 C7A_4 1.242(13) . ?
C10B_4 O2B_4 1.412(8) . ?
C10B_4 C9B_4 1.535(13) . ?
C4B_4 O4B_4 1.43(3) . ?
C4B_4 C3B_4 1.50(3) . ?
C4B_4 Na1B_4 3.032(19) . ?
C8B_4 C7B_4 1.778(10) . ?
C7B_4 O5B_4 1.432(9) . ?
Na1B_4 O2B_4 2.370(7) . ?
Na1B_4 O4B_4 2.373(5) . ?
Na1B_4 O3B_4 2.384(7) . ?
Na1B_4 O5B_4 2.414(5) . ?
C1B_4 O2B_4 1.413(9) . ?
C1B_4 C2B_4 1.517(9) . ?
O3B_4 C2B_4 1.416(10) . ?
O3B_4 C3B_4 1.426(8) . ?
O5B_4 C6B_4 1.420(10) . ?
O4B_4 C5B_4 1.44(2) . ?
C5B_4 C6B_4 1.48(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
B1_1 F1_1 Na1_3 100.28(15) . . ?
B1_1 F2_1 Na1_3 99.79(16) . . ?
N2_1 N1_1 C1_1 113.2(2) . . ?
N2_1 N1_1 B1_1 121.4(2) . . ?
C1_1 N1_1 B1_1 124.8(2) . . ?
C7_1 N2_1 N1_1 116.4(2) . . ?
C7_1 N3_1 N4_1 115.1(2) . . ?
N3_1 N4_1 C15_1 112.0(2) . . ?
N3_1 N4_1 B1_1 122.1(2) . . ?
C15_1 N4_1 B1_1 124.4(2) . . ?
C2_1 C1_1 C6_1 118.7(3) . . ?
C2_1 C1_1 N1_1 120.4(3) . . ?
C6_1 C1_1 N1_1 120.9(3) . . ?
C3_1 C2_1 C1_1 120.6(3) . . ?
C2_1 C3_1 C4_1 120.8(3) . . ?
C5_1 C4_1 C3_1 118.7(3) . . ?
C4_1 C5_1 C6_1 121.4(3) . . ?
C5_1 C6_1 C1_1 119.9(3) . . ?
N3_1 C7_1 N2_1 129.2(3) . . ?
N3_1 C7_1 C8_1 115.4(2) . . ?
N2_1 C7_1 C8_1 115.4(2) . . ?
C13_1 C8_1 C9_1 117.8(3) . . ?
C13_1 C8_1 C7_1 120.7(3) . . ?
C9_1 C8_1 C7_1 121.4(3) . . ?
C10_1 C9_1 C8_1 120.8(3) . . ?
C11_1 C10_1 C9_1 121.4(3) . . ?
C12_1 C11_1 C10_1 117.7(3) . . ?
C12_1 C11_1 C14_1 120.8(3) . . ?
C10_1 C11_1 C14_1 121.5(3) . . ?
C11_1 C12_1 C13_1 121.1(3) . . ?
C8_1 C13_1 C12_1 121.2(3) . . ?
C20_1 C15_1 C16_1 120.6(3) . . ?
C20_1 C15_1 N4_1 119.7(2) . . ?
C16_1 C15_1 N4_1 119.7(3) . . ?
C17_1 C16_1 C15_1 118.3(3) . . ?
C17_1 C16_1 C21_1 119.7(2) . . ?
C15_1 C16_1 C21_1 122.0(3) . . ?
C18_1 C17_1 C16_1 122.5(3) . . ?
C17_1 C18_1 C19_1 117.5(3) . . ?
C17_1 C18_1 C22_1 120.6(3) . . ?
C19_1 C18_1 C22_1 121.9(3) . . ?
C20_1 C19_1 C18_1 122.1(3) . . ?
C19_1 C20_1 C15_1 118.9(3) . . ?
C19_1 C20_1 C23_1 119.7(3) . . ?
C15_1 C20_1 C23_1 121.3(3) . . ?
F2_1 B1_1 F1_1 103.6(2) . . ?
F2_1 B1_1 N4_1 110.7(2) . . ?
F1_1 B1_1 N4_1 111.4(2) . . ?
F2_1 B1_1 N1_1 113.4(2) . . ?
F1_1 B1_1 N1_1 110.4(2) . . ?
N4_1 B1_1 N1_1 107.4(2) . . ?
F2_1 B1_1 Na1_3 52.67(13) . . ?
F1_1 B1_1 Na1_3 51.52(12) . . ?
N4_1 B1_1 Na1_3 119.03(19) . . ?
N1_1 B1_1 Na1_3 133.51(19) . . ?
B1_2 F1_2 Na1A_4 87.38(18) . . ?
B1_2 F2_2 Na1A_4 112.20(19) . . ?
B1_2 F2_2 Na1B_4 125.82(19) . . ?
N2_2 N1_2 C1_2 113.5(2) . . ?
N2_2 N1_2 B1_2 120.5(2) . . ?
C1_2 N1_2 B1_2 125.4(2) . . ?
C7_2 N2_2 N1_2 116.7(2) . . ?
C7_2 N3_2 N4_2 114.9(2) . . ?
N3_2 N4_2 C15_2 112.6(2) . . ?
N3_2 N4_2 B1_2 121.8(2) . . ?
C15_2 N4_2 B1_2 123.0(2) . . ?
C6_2 C1_2 C2_2 117.8(3) . . ?
C6_2 C1_2 N1_2 121.1(3) . . ?
C2_2 C1_2 N1_2 121.1(3) . . ?
C3_2 C2_2 C1_2 120.6(3) . . ?
C4_2 C3_2 C2_2 120.9(4) . . ?
C5_2 C4_2 C3_2 118.6(3) . . ?
C4_2 C5_2 C6_2 121.3(3) . . ?
C5_2 C6_2 C1_2 120.8(3) . . ?
N2_2 C7_2 N3_2 129.3(2) . . ?
N2_2 C7_2 C8_2 114.1(2) . . ?
N3_2 C7_2 C8_2 116.5(2) . . ?
C9_2 C8_2 C13_2 117.8(3) . . ?
C9_2 C8_2 C7_2 122.2(2) . . ?
C13_2 C8_2 C7_2 120.0(3) . . ?
C10_2 C9_2 C8_2 120.9(3) . . ?
C9_2 C10_2 C11_2 121.4(3) . . ?
C10_2 C11_2 C12_2 117.5(3) . . ?
C10_2 C11_2 C14_2 121.5(3) . . ?
C12_2 C11_2 C14_2 121.0(3) . . ?
C13_2 C12_2 C11_2 121.7(3) . . ?
C12_2 C13_2 C8_2 120.7(3) . . ?
C16_2 C15_2 C20_2 120.2(3) . . ?
C16_2 C15_2 N4_2 119.8(3) . . ?
C20_2 C15_2 N4_2 119.9(2) . . ?
C17_2 C16_2 C15_2 118.3(3) . . ?
C17_2 C16_2 C21_2 119.6(3) . . ?
C15_2 C16_2 C21_2 122.1(3) . . ?
C18_2 C17_2 C16_2 122.9(3) . . ?
C17_2 C18_2 C19_2 117.3(3) . . ?
C17_2 C18_2 C22_2 121.6(3) . . ?
C19_2 C18_2 C22_2 121.1(3) . . ?
C20_2 C19_2 C18_2 122.5(3) . . ?
C19_2 C20_2 C15_2 118.8(3) . . ?
C19_2 C20_2 C23_2 119.8(3) . . ?
C15_2 C20_2 C23_2 121.4(3) . . ?
F1_2 B1_2 F2_2 105.8(2) . . ?
F1_2 B1_2 N4_2 111.1(3) . . ?
F2_2 B1_2 N4_2 111.2(3) . . ?
F1_2 B1_2 N1_2 113.1(3) . . ?
F2_2 B1_2 N1_2 108.6(3) . . ?
N4_2 B1_2 N1_2 107.3(2) . . ?
F1_2 B1_2 Na1A_4 65.05(16) . . ?
F2_2 B1_2 Na1A_4 41.42(13) . . ?
N4_2 B1_2 Na1A_4 132.8(2) . . ?
N1_2 B1_2 Na1A_4 117.5(2) . . ?
O1_3 Na1_3 F1_1 141.22(8) . . ?
O1_3 Na1_3 O4_3 109.53(9) . . ?
F1_1 Na1_3 O4_3 84.67(7) . . ?
O1_3 Na1_3 F2_1 108.28(7) . . ?
F1_1 Na1_3 F2_1 55.50(6) . . ?
O4_3 Na1_3 F2_1 138.96(8) . . ?
O1_3 Na1_3 O3_3 116.48(8) . . ?
F1_1 Na1_3 O3_3 102.28(7) . . ?
O4_3 Na1_3 O3_3 68.89(7) . . ?
F2_1 Na1_3 O3_3 107.13(8) . . ?
O1_3 Na1_3 O5_3 67.95(7) . . ?
F1_1 Na1_3 O5_3 86.75(7) . . ?
O4_3 Na1_3 O5_3 66.79(7) . . ?
F2_1 Na1_3 O5_3 114.98(7) . . ?
O3_3 Na1_3 O5_3 133.61(8) . . ?
O1_3 Na1_3 O2_3 69.05(7) . . ?
F1_1 Na1_3 O2_3 129.56(8) . . ?
O4_3 Na1_3 O2_3 129.32(8) . . ?
F2_1 Na1_3 O2_3 79.42(7) . . ?
O3_3 Na1_3 O2_3 67.95(7) . . ?
O5_3 Na1_3 O2_3 136.99(8) . . ?
O1_3 Na1_3 B1_1 125.86(9) . . ?
F1_1 Na1_3 B1_1 28.20(7) . . ?
O4_3 Na1_3 B1_1 112.77(9) . . ?
F2_1 Na1_3 B1_1 27.54(7) . . ?
O3_3 Na1_3 B1_1 109.35(9) . . ?
O5_3 Na1_3 B1_1 99.81(9) . . ?
O2_3 Na1_3 B1_1 105.62(9) . . ?
C24_3 O1_3 C33_3 113.6(2) . . ?
C24_3 O1_3 Na1_3 114.41(19) . . ?
C33_3 O1_3 Na1_3 111.01(17) . . ?
C26_3 O2_3 C25_3 113.6(2) . . ?
C26_3 O2_3 Na1_3 111.90(16) . . ?
C25_3 O2_3 Na1_3 108.50(17) . . ?
C27_3 O3_3 C28_3 112.3(2) . . ?
C27_3 O3_3 Na1_3 115.35(17) . . ?
C28_3 O3_3 Na1_3 113.27(17) . . ?
C29_3 O4_3 C30_3 114.0(2) . . ?
C29_3 O4_3 Na1_3 106.97(18) . . ?
C30_3 O4_3 Na1_3 107.45(17) . . ?
C31_3 O5_3 C32_3 114.1(3) . . ?
C31_3 O5_3 Na1_3 114.32(18) . . ?
C32_3 O5_3 Na1_3 113.44(18) . . ?
O1_3 C24_3 C25_3 108.3(2) . . ?
O2_3 C25_3 C24_3 107.6(2) . . ?
O2_3 C26_3 C27_3 112.7(3) . . ?
O3_3 C27_3 C26_3 107.5(2) . . ?
O3_3 C28_3 C29_3 107.4(2) . . ?
O4_3 C29_3 C28_3 106.4(3) . . ?
O4_3 C30_3 C31_3 106.0(3) . . ?
O5_3 C31_3 C30_3 109.0(3) . . ?
O5_3 C32_3 C33_3 108.4(3) . . ?
O1_3 C33_3 C32_3 107.2(3) . . ?
C8B_4 O1_4 C9B_4 103.0(6) . . ?
C9A_4 O1_4 C8A_4 125.5(7) . . ?
C8B_4 O1_4 Na1B_4 126.0(3) . . ?
C9B_4 O1_4 Na1B_4 108.5(5) . . ?
C9A_4 O1_4 Na1A_4 116.4(7) . . ?
C8A_4 O1_4 Na1A_4 98.6(3) . . ?
F2_2 Na1A_4 O3A_4 85.09(17) . . ?
F2_2 Na1A_4 O4A_4 132.4(4) . . ?
O3A_4 Na1A_4 O4A_4 71.5(4) . . ?
F2_2 Na1A_4 O1_4 98.76(13) . . ?
O3A_4 Na1A_4 O1_4 136.4(2) . . ?
O4A_4 Na1A_4 O1_4 126.9(4) . . ?
F2_2 Na1A_4 O2A_4 100.6(2) . . ?
O3A_4 Na1A_4 O2A_4 69.1(3) . . ?
O4A_4 Na1A_4 O2A_4 108.2(4) . . ?
O1_4 Na1A_4 O2A_4 67.5(2) . . ?
F2_2 Na1A_4 O5A_4 129.17(18) . . ?
O3A_4 Na1A_4 O5A_4 138.1(2) . . ?
O4A_4 Na1A_4 O5A_4 67.3(4) . . ?
O1_4 Na1A_4 O5A_4 69.33(14) . . ?
O2A_4 Na1A_4 O5A_4 117.3(2) . . ?
F2_2 Na1A_4 F1_2 53.66(9) . . ?
O3A_4 Na1A_4 F1_2 76.13(16) . . ?
O4A_4 Na1A_4 F1_2 80.3(4) . . ?
O1_4 Na1A_4 F1_2 139.51(14) . . ?
O2A_4 Na1A_4 F1_2 138.6(2) . . ?
O5A_4 Na1A_4 F1_2 103.48(16) . . ?
F2_2 Na1A_4 B1_2 26.38(9) . . ?
O3A_4 Na1A_4 B1_2 82.46(16) . . ?
O4A_4 Na1A_4 B1_2 107.7(4) . . ?
O1_4 Na1A_4 B1_2 118.47(13) . . ?
O2A_4 Na1A_4 B1_2 123.1(2) . . ?
O5A_4 Na1A_4 B1_2 116.75(17) . . ?
F1_2 Na1A_4 B1_2 27.57(8) . . ?
F2_2 Na1A_4 C8A_4 111.8(2) . . ?
O3A_4 Na1A_4 C8A_4 156.1(3) . . ?
O4A_4 Na1A_4 C8A_4 105.1(4) . . ?
O1_4 Na1A_4 C8A_4 28.47(18) . . ?
O2A_4 Na1A_4 C8A_4 90.6(3) . . ?
O5A_4 Na1A_4 C8A_4 41.3(2) . . ?
F1_2 Na1A_4 C8A_4 127.3(2) . . ?
B1_2 Na1A_4 C8A_4 120.3(2) . . ?
O2A_4 C1A_4 C2A_4 108.2(8) . . ?
C1A_4 O2A_4 C10A_4 114.7(8) . . ?
C1A_4 O2A_4 Na1A_4 108.5(6) . . ?
C10A_4 O2A_4 Na1A_4 107.6(5) . . ?
O3A_4 C2A_4 C1A_4 107.3(9) . . ?
C2A_4 O3A_4 C3A_4 113.9(14) . . ?
C2A_4 O3A_4 Na1A_4 116.6(7) . . ?
C3A_4 O3A_4 Na1A_4 108.7(10) . . ?
C7A_4 O5A_4 C6A_4 115.6(5) . . ?
C7A_4 O5A_4 Na1A_4 107.0(5) . . ?
C6A_4 O5A_4 Na1A_4 113.4(4) . . ?
C5A_4 O4A_4 C4A_4 116.5(11) . . ?
C5A_4 O4A_4 Na1A_4 113.0(9) . . ?
C4A_4 O4A_4 Na1A_4 112.2(8) . . ?
O4A_4 C4A_4 C3A_4 108.0(11) . . ?
O2A_4 C10A_4 C9A_4 109.6(10) . . ?
O4A_4 C5A_4 C6A_4 108.3(10) . . ?
O1_4 C9A_4 C10A_4 107.3(12) . . ?
C7A_4 C8A_4 O1_4 124.0(9) . . ?
C7A_4 C8A_4 Na1A_4 88.2(5) . . ?
O1_4 C8A_4 Na1A_4 52.9(3) . . ?
C8A_4 C7A_4 O5A_4 98.7(8) . . ?
O5A_4 C6A_4 C5A_4 111.2(7) . . ?
O3A_4 C3A_4 C4A_4 111(2) . . ?
O2B_4 C10B_4 C9B_4 106.4(8) . . ?
O1_4 C9B_4 C10B_4 108.7(8) . . ?
O4B_4 C4B_4 C3B_4 107.8(18) . . ?
O4B_4 C4B_4 Na1B_4 49.7(6) . . ?
C3B_4 C4B_4 Na1B_4 84.2(9) . . ?
O1_4 C8B_4 C7B_4 101.0(6) . . ?
O5B_4 C7B_4 C8B_4 111.7(6) . . ?
F2_2 Na1B_4 O2B_4 115.9(2) . . ?
F2_2 Na1B_4 O4B_4 117.84(16) . . ?
O2B_4 Na1B_4 O4B_4 113.0(2) . . ?
F2_2 Na1B_4 O1_4 95.32(12) . . ?
O2B_4 Na1B_4 O1_4 72.18(17) . . ?
O4B_4 Na1B_4 O1_4 135.30(17) . . ?
F2_2 Na1B_4 O3B_4 93.85(18) . . ?
O2B_4 Na1B_4 O3B_4 69.7(2) . . ?
O4B_4 Na1B_4 O3B_4 69.7(2) . . ?
O1_4 Na1B_4 O3B_4 140.9(2) . . ?
F2_2 Na1B_4 O5B_4 111.56(17) . . ?
O2B_4 Na1B_4 O5B_4 121.1(2) . . ?
O4B_4 Na1B_4 O5B_4 69.73(18) . . ?
O1_4 Na1B_4 O5B_4 70.58(14) . . ?
O3B_4 Na1B_4 O5B_4 138.7(2) . . ?
F2_2 Na1B_4 C4B_4 97.0(5) . . ?
O2B_4 Na1B_4 C4B_4 112.9(6) . . ?
O4B_4 Na1B_4 C4B_4 27.3(5) . . ?
O1_4 Na1B_4 C4B_4 162.5(4) . . ?
O3B_4 Na1B_4 C4B_4 50.3(5) . . ?
O5B_4 Na1B_4 C4B_4 93.3(4) . . ?
O2B_4 C1B_4 C2B_4 108.3(6) . . ?
C2B_4 O3B_4 C3B_4 113.2(6) . . ?
C2B_4 O3B_4 Na1B_4 115.8(4) . . ?
C3B_4 O3B_4 Na1B_4 114.5(4) . . ?
O3B_4 C3B_4 C4B_4 108.3(8) . . ?
C10B_4 O2B_4 C1B_4 113.5(6) . . ?
C10B_4 O2B_4 Na1B_4 111.4(5) . . ?
C1B_4 O2B_4 Na1B_4 109.5(4) . . ?
O3B_4 C2B_4 C1B_4 107.7(7) . . ?
C6B_4 O5B_4 C7B_4 112.7(8) . . ?
C6B_4 O5B_4 Na1B_4 113.2(7) . . ?
C7B_4 O5B_4 Na1B_4 112.9(4) . . ?
C4B_4 O4B_4 C5B_4 114.6(15) . . ?
C4B_4 O4B_4 Na1B_4 103.1(7) . . ?
C5B_4 O4B_4 Na1B_4 109.2(8) . . ?
O4B_4 C5B_4 C6B_4 106.9(14) . . ?
O5B_4 C6B_4 C5B_4 107.6(12) . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_Cp2Co-1f
_database_code_depnum_ccdc_archive 'CCDC 1471291'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H26 B Co F7 N4'
_chemical_formula_weight         669.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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'

_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                   15.6779(3)
_cell_length_b                   24.3649(5)
_cell_length_c                   15.2499(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.9593(9)
_cell_angle_gamma                90
_cell_volume                     5811.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      65.24

_exptl_crystal_description       platelet
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_F_000             2728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.01
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_max          0.16
_exptl_absorpt_coefficient_mu    5.302
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5549
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54491
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.568
_diffrn_reflns_theta_max         65.300
_diffrn_reflns_theta_full        65.301
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             9905
_reflns_number_gt                8395
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0328P)²+3.9125P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9905
_refine_ls_number_parameters     817
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
CO1 Co -0.01692(2) 0.23049(2) 0.44687(2) 0.01806(9) Uani 1 1 d . . . . .
CO2 Co 0.47162(2) 0.25671(2) 0.31016(2) 0.02089(9) Uani 1 1 d . . . . .
F1 F 0.66120(7) 0.42126(5) 0.30820(8) 0.0293(3) Uani 1 1 d . . . . .
F2 F 0.73184(10) 0.47765(5) 0.44462(8) 0.0407(4) Uani 1 1 d . . . . .
F3 F 0.90480(11) 0.48627(6) 0.47001(9) 0.0488(4) Uani 1 1 d . . . . .
F4 F 1.00634(8) 0.43414(6) 0.35793(10) 0.0434(4) Uani 1 1 d . . . . .
F5 F 0.93630(7) 0.38103(5) 0.21670(8) 0.0279(3) Uani 1 1 d . . . . .
F6 F 0.59597(7) 0.28856(5) 0.02389(7) 0.0213(3) Uani 1 1 d . . . . .
F7 F 0.71371(7) 0.30790(5) -0.04753(7) 0.0252(3) Uani 1 1 d . . . . .
F8 F 0.17198(8) 0.41430(6) 0.42931(8) 0.0326(3) Uani 1 1 d . . . . .
F9 F 0.25606(9) 0.47196(6) 0.31142(8) 0.0408(4) Uani 1 1 d . . . . .
F10 F 0.42745(10) 0.48753(7) 0.33779(9) 0.0498(4) Uani 1 1 d . . . . .
F11 F 0.51489(8) 0.44387(6) 0.48083(10) 0.0433(4) Uani 1 1 d . . . . .
F12 F 0.43051(8) 0.39015(6) 0.60213(9) 0.0355(3) Uani 1 1 d . . . . .
F13 F 0.08248(7) 0.30119(5) 0.72505(8) 0.0272(3) Uani 1 1 d . . . . .
F14 F 0.20731(8) 0.31190(5) 0.80710(8) 0.0287(3) Uani 1 1 d . . . . .
N1 N 0.73274(10) 0.28779(7) 0.10912(11) 0.0186(4) Uani 1 1 d . . . . .
N2 N 0.77014(10) 0.31670(7) 0.17893(11) 0.0185(4) Uani 1 1 d . . . . .
N3 N 0.70755(10) 0.40195(7) 0.12346(11) 0.0179(4) Uani 1 1 d . . . . .
N4 N 0.66626(10) 0.37461(7) 0.05567(11) 0.0180(4) Uani 1 1 d . . . . .
N5 N 0.21396(10) 0.29156(7) 0.65212(11) 0.0192(4) Uani 1 1 d . . . . .
N6 N 0.25694(10) 0.31819(7) 0.58883(11) 0.0206(4) Uani 1 1 d . . . . .
N7 N 0.20789(10) 0.40683(7) 0.63713(11) 0.0210(4) Uani 1 1 d . . . . .
N8 N 0.16399(10) 0.38227(7) 0.70034(11) 0.0201(4) Uani 1 1 d . . . . .
C1 C 0.74469(12) 0.23075(9) 0.11499(14) 0.0204(5) Uani 1 1 d . . . . .
C2 C 0.71676(13) 0.19725(9) 0.04412(16) 0.0266(5) Uani 1 1 d . . . . .
H2 H 0.6938 0.2135 -0.0090 0.032 Uiso 1 1 calc R U . . .
C3 C 0.72234(14) 0.14070(10) 0.05070(18) 0.0354(6) Uani 1 1 d . . . . .
H3 H 0.7008 0.1185 0.0029 0.042 Uiso 1 1 calc R U . . .
C4 C 0.75856(16) 0.11621(10) 0.12519(18) 0.0403(7) Uani 1 1 d . . . . .
H4 H 0.7622 0.0774 0.1294 0.048 Uiso 1 1 calc R U . . .
C5 C 0.78973(17) 0.14911(10) 0.19401(18) 0.0404(6) Uani 1 1 d . . . . .
H5 H 0.8163 0.1326 0.2453 0.049 Uiso 1 1 calc R U . . .
C6 C 0.78290(14) 0.20575(10) 0.18955(16) 0.0301(5) Uani 1 1 d . . . . .
H6 H 0.8044 0.2276 0.2377 0.036 Uiso 1 1 calc R U . . .
C7 C 0.75550(12) 0.37042(8) 0.17867(13) 0.0168(4) Uani 1 1 d . . . . .
C8 C 0.79638(13) 0.40059(8) 0.25580(13) 0.0181(4) Uani 1 1 d . . . . .
C9 C 0.74718(13) 0.42613(9) 0.31630(14) 0.0218(5) Uani 1 1 d . . . . .
C10 C 0.78254(16) 0.45487(9) 0.38718(14) 0.0276(5) Uani 1 1 d . . . . .
C11 C 0.86984(17) 0.45855(9) 0.40040(15) 0.0312(6) Uani 1 1 d . . . . .
C12 C 0.92108(14) 0.43280(9) 0.34372(15) 0.0287(5) Uani 1 1 d . . . . .
C13 C 0.88405(13) 0.40490(9) 0.27184(14) 0.0212(5) Uani 1 1 d . . . . .
C14 C 0.61205(12) 0.40846(8) -0.00138(13) 0.0177(4) Uani 1 1 d . . . . .
C15 C 0.52392(12) 0.41027(9) 0.00987(13) 0.0191(4) Uani 1 1 d . . . . .
C16 C 0.47171(12) 0.43962(9) -0.05059(14) 0.0219(5) Uani 1 1 d . . . . .
H16 H 0.4121 0.4411 -0.0432 0.026 Uiso 1 1 calc R U . . .
C17 C 0.50332(13) 0.46678(9) -0.12119(14) 0.0223(5) Uani 1 1 d . . . . .
C18 C 0.59137(13) 0.46631(9) -0.12815(14) 0.0232(5) Uani 1 1 d . . . . .
H18 H 0.6145 0.4861 -0.1747 0.028 Uiso 1 1 calc R U . . .
C19 C 0.64634(12) 0.43784(9) -0.06921(14) 0.0203(5) Uani 1 1 d . . . . .
C20 C 0.48633(13) 0.38141(10) 0.08572(15) 0.0277(5) Uani 1 1 d . . . . .
H20A H 0.4642 0.3455 0.0663 0.042 Uiso 1 1 calc R U . . .
H20B H 0.4397 0.4036 0.1067 0.042 Uiso 1 1 calc R U . . .
H20C H 0.5307 0.3764 0.1335 0.042 Uiso 1 1 calc R U . . .
C21 C 0.44502(14) 0.49661(10) -0.18802(15) 0.0285(5) Uani 1 1 d . . . . .
H21A H 0.3979 0.5135 -0.1586 0.043 Uiso 1 1 calc R U . . .
H21B H 0.4219 0.4705 -0.2325 0.043 Uiso 1 1 calc R U . . .
H21C H 0.4774 0.5252 -0.2164 0.043 Uiso 1 1 calc R U . . .
C22 C 0.74126(13) 0.43994(10) -0.07871(16) 0.0310(6) Uani 1 1 d . . . . .
H22A H 0.7605 0.4046 -0.1008 0.047 Uiso 1 1 calc R U . . .
H22B H 0.7710 0.4476 -0.0214 0.047 Uiso 1 1 calc R U . . .
H22C H 0.7540 0.4690 -0.1202 0.047 Uiso 1 1 calc R U . . .
C23 C 0.21914(12) 0.23410(9) 0.64678(14) 0.0196(5) Uani 1 1 d . . . . .
C24 C 0.25503(13) 0.20795(9) 0.57676(15) 0.0239(5) Uani 1 1 d . . . . .
H24 H 0.2762 0.2291 0.5307 0.029 Uiso 1 1 calc R U . . .
C25 C 0.25984(13) 0.15124(10) 0.57414(16) 0.0281(5) Uani 1 1 d . . . . .
H25 H 0.2850 0.1340 0.5263 0.034 Uiso 1 1 calc R U . . .
C26 C 0.22878(13) 0.11904(10) 0.63963(15) 0.0273(5) Uani 1 1 d . . . . .
H26 H 0.2327 0.0802 0.6374 0.033 Uiso 1 1 calc R U . . .
C27 C 0.19188(13) 0.14482(9) 0.70846(15) 0.0245(5) Uani 1 1 d . . . . .
H27 H 0.1695 0.1233 0.7535 0.029 Uiso 1 1 calc R U . . .
C28 C 0.18710(12) 0.20140(9) 0.71264(14) 0.0219(5) Uani 1 1 d . . . . .
H28 H 0.1618 0.2183 0.7606 0.026 Uiso 1 1 calc R U . . .
C29 C 0.25058(13) 0.37239(9) 0.58820(13) 0.0198(5) Uani 1 1 d . . . . .
C30 C 0.29848(13) 0.40063(9) 0.51948(14) 0.0206(5) Uani 1 1 d . . . . .
C31 C 0.25670(13) 0.42159(9) 0.44416(14) 0.0231(5) Uani 1 1 d . . . . .
C32 C 0.29872(15) 0.45086(9) 0.38338(14) 0.0272(5) Uani 1 1 d . . . . .
C33 C 0.38549(16) 0.45896(10) 0.39662(15) 0.0313(6) Uani 1 1 d . . . . .
C34 C 0.42967(14) 0.43747(10) 0.46947(16) 0.0290(5) Uani 1 1 d . . . . .
C35 C 0.38588(14) 0.40911(9) 0.52996(15) 0.0253(5) Uani 1 1 d . . . . .
C36 C 0.11425(12) 0.42060(8) 0.74774(13) 0.0185(4) Uani 1 1 d . . . . .
C37 C 0.03001(13) 0.43197(9) 0.71683(14) 0.0224(5) Uani 1 1 d . . . . .
C38 C -0.01831(13) 0.46702(9) 0.76575(15) 0.0245(5) Uani 1 1 d . . . . .
H38 H -0.0760 0.4742 0.7460 0.029 Uiso 1 1 calc R U . . .
C39 C 0.01510(13) 0.49175(9) 0.84239(14) 0.0237(5) Uani 1 1 d . . . . .
C40 C 0.09981(13) 0.48161(9) 0.86872(14) 0.0239(5) Uani 1 1 d . . . . .
H40 H 0.1243 0.4993 0.9200 0.029 Uiso 1 1 calc R U . . .
C41 C 0.15043(13) 0.44641(9) 0.82289(14) 0.0213(5) Uani 1 1 d . . . . .
C42 C -0.00758(15) 0.40708(10) 0.63280(15) 0.0317(6) Uani 1 1 d . . . . .
H42A H -0.0213 0.3684 0.6427 0.048 Uiso 1 1 calc R U . . .
H42B H 0.0338 0.4097 0.5877 0.048 Uiso 1 1 calc R U . . .
H42C H -0.0598 0.4269 0.6131 0.048 Uiso 1 1 calc R U . . .
C43 C -0.03886(15) 0.52992(10) 0.89323(17) 0.0342(6) Uani 1 1 d . . . . .
H43A H -0.0036 0.5461 0.9421 0.051 Uiso 1 1 calc R U . . .
H43B H -0.0861 0.5093 0.9163 0.051 Uiso 1 1 calc R U . . .
H43C H -0.0619 0.5591 0.8543 0.051 Uiso 1 1 calc R U . . .
C44 C 0.24283(14) 0.43770(11) 0.85300(17) 0.0337(6) Uani 1 1 d . . . . .
H44A H 0.2602 0.4650 0.8980 0.051 Uiso 1 1 calc R U . . .
H44B H 0.2782 0.4417 0.8029 0.051 Uiso 1 1 calc R U . . .
H44C H 0.2503 0.4008 0.8778 0.051 Uiso 1 1 calc R U . . .
C45 C -0.06742(14) 0.17249(10) 0.52298(16) 0.0313(6) Uani 1 1 d . . . . .
H45 H -0.1046 0.1793 0.5725 0.038 Uiso 1 1 calc R U . . .
C46 C 0.02355(15) 0.16897(10) 0.52972(16) 0.0322(6) Uani 1 1 d . . . . .
H46 H 0.0616 0.1731 0.5847 0.039 Uiso 1 1 calc R U . . .
C47 C 0.05028(14) 0.15929(9) 0.44471(16) 0.0295(5) Uani 1 1 d . . . . .
H47 H 0.1108 0.1555 0.4289 0.035 Uiso 1 1 calc R U . . .
C48 C -0.02299(14) 0.15662(9) 0.38557(17) 0.0309(6) Uani 1 1 d . . . . .
H48 H -0.0234 0.1504 0.3207 0.037 Uiso 1 1 calc R U . . .
C49 C -0.09570(14) 0.16501(9) 0.43395(16) 0.0296(5) Uani 1 1 d . . . . .
H49 H -0.1565 0.1655 0.4093 0.036 Uiso 1 1 calc R U . . .
C50 C -0.00340(15) 0.28751(9) 0.35205(15) 0.0291(5) Uani 1 1 d . . . . .
H50 H 0.0021 0.2800 0.2882 0.035 Uiso 1 1 calc R U . . .
C51 C -0.08108(15) 0.29606(9) 0.39323(16) 0.0294(5) Uani 1 1 d . . . . .
H51 H -0.1399 0.2954 0.3634 0.035 Uiso 1 1 calc R U . . .
C52 C -0.06072(14) 0.30483(9) 0.48393(16) 0.0282(5) Uani 1 1 d . . . . .
H52 H -0.1024 0.3116 0.5295 0.034 Uiso 1 1 calc R U . . .
C53 C 0.02966(14) 0.30191(9) 0.49885(16) 0.0280(5) Uani 1 1 d . . . . .
H53 H 0.0627 0.3062 0.5569 0.034 Uiso 1 1 calc R U . . .
C54 C 0.06475(15) 0.29119(10) 0.41781(16) 0.0304(5) Uani 1 1 d . . . . .
H54 H 0.1269 0.2867 0.4085 0.036 Uiso 1 1 calc R U . . .
C55 C 0.50526(15) 0.30992(11) 0.40923(16) 0.0357(6) Uani 1 1 d . . . . .
H55 H 0.5618 0.3110 0.4438 0.043 Uiso 1 1 calc R U . . .
C56 C 0.48388(15) 0.33882(10) 0.33031(17) 0.0344(6) Uani 1 1 d . . . . .
H56 H 0.5223 0.3641 0.2996 0.041 Uiso 1 1 calc R U . . .
C57 C 0.39847(14) 0.32553(10) 0.30262(16) 0.0310(6) Uani 1 1 d . . . . .
H57 H 0.3658 0.3397 0.2487 0.037 Uiso 1 1 calc R U . . .
C58 C 0.36737(15) 0.28847(11) 0.36439(16) 0.0361(6) Uani 1 1 d . . . . .
H58 H 0.3089 0.2718 0.3617 0.043 Uiso 1 1 calc R U . . .
C59 C 0.43395(16) 0.27865(12) 0.43013(15) 0.0370(6) Uani 1 1 d . . . . .
H59 H 0.4308 0.2539 0.4822 0.044 Uiso 1 1 calc R U . . .
C60 C 0.53700(15) 0.23503(11) 0.20488(16) 0.0333(6) Uani 1 1 d . . . . .
H60 H 0.5656 0.2606 0.1649 0.040 Uiso 1 1 calc R U . . .
C61 C 0.45123(16) 0.21662(11) 0.19442(15) 0.0335(6) Uani 1 1 d . . . . .
H61 H 0.4085 0.2270 0.1455 0.040 Uiso 1 1 calc R U . . .
C62 C 0.43633(18) 0.18151(11) 0.26481(17) 0.0407(6) Uani 1 1 d . . . . .
H62 H 0.3813 0.1625 0.2746 0.049 Uiso 1 1 calc R U . . .
C63 C 0.51292(18) 0.17791(10) 0.31953(16) 0.0394(6) Uani 1 1 d . . . . .
H63 H 0.5213 0.1560 0.3749 0.047 Uiso 1 1 calc R U . . .
C64 C 0.57475(16) 0.21087(11) 0.28302(16) 0.0355(6) Uani 1 1 d . . . . .
H64 H 0.6348 0.2166 0.3079 0.043 Uiso 1 1 calc R U . . .
B1 B 0.67693(14) 0.31449(10) 0.03436(16) 0.0185(5) Uani 1 1 d . . . . .
B2 B 0.16650(15) 0.32171(10) 0.72274(16) 0.0208(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
CO1 C49 2.019(2) . ?
CO1 C45 2.024(2) . ?
CO1 C54 2.025(2) . ?
CO1 C50 2.027(2) . ?
CO1 C53 2.027(2) . ?
CO1 C48 2.027(2) . ?
CO1 C51 2.030(2) . ?
CO1 C52 2.031(2) . ?
CO1 C47 2.031(2) . ?
CO1 C46 2.033(2) . ?
CO2 C62 2.022(3) . ?
CO2 C61 2.023(2) . ?
CO2 C63 2.028(3) . ?
CO2 C57 2.030(2) . ?
CO2 C56 2.031(3) . ?
CO2 C64 2.031(2) . ?
CO2 C59 2.032(2) . ?
CO2 C55 2.033(2) . ?
CO2 C60 2.033(2) . ?
CO2 C58 2.035(2) . ?
F1 C9 1.350(2) . ?
F2 C10 1.343(3) . ?
F3 C11 1.343(2) . ?
F4 C12 1.340(2) . ?
F5 C13 1.346(2) . ?
F6 B1 1.417(2) . ?
F7 B1 1.420(3) . ?
F8 C31 1.344(2) . ?
F9 C32 1.347(3) . ?
F10 C33 1.343(3) . ?
F11 C34 1.344(3) . ?
F12 C35 1.345(3) . ?
F13 B2 1.412(3) . ?
F14 B2 1.417(3) . ?
N1 N2 1.374(2) . ?
N1 C1 1.404(3) . ?
N1 B1 1.533(3) . ?
N2 C7 1.329(3) . ?
N3 C7 1.333(3) . ?
N3 N4 1.356(2) . ?
N4 C14 1.434(3) . ?
N4 B1 1.512(3) . ?
N5 N6 1.377(2) . ?
N5 C23 1.405(3) . ?
N5 B2 1.537(3) . ?
N6 C29 1.324(3) . ?
N7 C29 1.333(3) . ?
N7 N8 1.361(2) . ?
N8 C36 1.443(3) . ?
N8 B2 1.514(3) . ?
C1 C6 1.389(3) . ?
C1 C2 1.400(3) . ?
C2 C3 1.384(3) . ?
C3 C4 1.371(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.385(3) . ?
C7 C8 1.493(3) . ?
C8 C13 1.383(3) . ?
C8 C9 1.390(3) . ?
C9 C10 1.372(3) . ?
C10 C11 1.372(3) . ?
C11 C12 1.372(3) . ?
C12 C13 1.383(3) . ?
C14 C19 1.396(3) . ?
C14 C15 1.405(3) . ?
C15 C16 1.388(3) . ?
C15 C20 1.508(3) . ?
C16 C17 1.384(3) . ?
C17 C18 1.392(3) . ?
C17 C21 1.508(3) . ?
C18 C19 1.387(3) . ?
C19 C22 1.506(3) . ?
C23 C24 1.395(3) . ?
C23 C28 1.402(3) . ?
C24 C25 1.384(3) . ?
C25 C26 1.385(3) . ?
C26 C27 1.384(3) . ?
C27 C28 1.382(3) . ?
C29 C30 1.498(3) . ?
C30 C31 1.380(3) . ?
C30 C35 1.384(3) . ?
C31 C32 1.373(3) . ?
C32 C33 1.376(3) . ?
C33 C34 1.372(3) . ?
C34 C35 1.374(3) . ?
C36 C41 1.393(3) . ?
C36 C37 1.399(3) . ?
C37 C38 1.392(3) . ?
C37 C42 1.501(3) . ?
C38 C39 1.385(3) . ?
C39 C40 1.383(3) . ?
C39 C43 1.507(3) . ?
C40 C41 1.389(3) . ?
C41 C44 1.504(3) . ?
C45 C49 1.411(3) . ?
C45 C46 1.425(3) . ?
C46 C47 1.410(3) . ?
C47 C48 1.412(3) . ?
C48 C49 1.415(3) . ?
C50 C54 1.417(3) . ?
C50 C51 1.424(3) . ?
C51 C52 1.414(3) . ?
C52 C53 1.421(3) . ?
C53 C54 1.411(3) . ?
C55 C59 1.407(4) . ?
C55 C56 1.415(4) . ?
C56 C57 1.413(3) . ?
C57 C58 1.416(4) . ?
C58 C59 1.417(3) . ?
C60 C61 1.416(3) . ?
C60 C64 1.421(3) . ?
C61 C62 1.405(4) . ?
C62 C63 1.417(4) . ?
C63 C64 1.403(4) . ?

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
C49 CO1 C45 40.84(10) . . ?
C49 CO1 C54 161.34(10) . . ?
C45 CO1 C54 155.99(10) . . ?
C49 CO1 C50 124.43(10) . . ?
C45 CO1 C50 162.14(10) . . ?
C54 CO1 C50 40.93(10) . . ?
C49 CO1 C53 156.62(9) . . ?
C45 CO1 C53 121.31(10) . . ?
C54 CO1 C53 40.77(9) . . ?
C50 CO1 C53 68.78(10) . . ?
C49 CO1 C48 40.93(9) . . ?
C45 CO1 C48 68.71(10) . . ?
C54 CO1 C48 123.89(9) . . ?
C50 CO1 C48 106.46(10) . . ?
C53 CO1 C48 161.18(9) . . ?
C49 CO1 C51 107.44(10) . . ?
C45 CO1 C51 125.31(9) . . ?
C54 CO1 C51 68.91(10) . . ?
C50 CO1 C51 41.09(9) . . ?
C53 CO1 C51 68.72(10) . . ?
C48 CO1 C51 120.44(10) . . ?
C49 CO1 C52 121.04(9) . . ?
C45 CO1 C52 108.06(10) . . ?
C54 CO1 C52 68.94(9) . . ?
C50 CO1 C52 68.98(10) . . ?
C53 CO1 C52 41.00(9) . . ?
C48 CO1 C52 156.06(9) . . ?
C51 CO1 C52 40.76(9) . . ?
C49 CO1 C47 68.78(9) . . ?
C45 CO1 C47 68.71(9) . . ?
C54 CO1 C47 106.48(9) . . ?
C50 CO1 C47 119.59(9) . . ?
C53 CO1 C47 124.49(9) . . ?
C48 CO1 C47 40.73(9) . . ?
C51 CO1 C47 155.35(10) . . ?
C52 CO1 C47 162.16(10) . . ?
C49 CO1 C46 68.94(10) . . ?
C45 CO1 C46 41.13(9) . . ?
C54 CO1 C46 119.96(10) . . ?
C50 CO1 C46 154.82(9) . . ?
C53 CO1 C46 107.54(10) . . ?
C48 CO1 C46 68.58(10) . . ?
C51 CO1 C46 162.81(10) . . ?
C52 CO1 C46 125.56(10) . . ?
C47 CO1 C46 40.58(10) . . ?
C62 CO2 C61 40.64(10) . . ?
C62 CO2 C63 40.95(11) . . ?
C61 CO2 C63 68.58(10) . . ?
C62 CO2 C57 126.08(11) . . ?
C61 CO2 C57 107.14(10) . . ?
C63 CO2 C57 164.20(11) . . ?
C62 CO2 C56 164.81(10) . . ?
C61 CO2 C56 127.96(11) . . ?
C63 CO2 C56 153.56(10) . . ?
C57 CO2 C56 40.73(9) . . ?
C62 CO2 C64 68.58(11) . . ?
C61 CO2 C64 68.70(10) . . ?
C63 CO2 C64 40.44(11) . . ?
C57 CO2 C64 153.79(11) . . ?
C56 CO2 C64 120.27(10) . . ?
C62 CO2 C59 117.16(11) . . ?
C61 CO2 C59 150.93(11) . . ?
C63 CO2 C59 107.26(11) . . ?
C57 CO2 C59 68.63(10) . . ?
C56 CO2 C59 68.60(11) . . ?
C64 CO2 C59 127.80(10) . . ?
C62 CO2 C55 152.01(11) . . ?
C61 CO2 C55 166.81(11) . . ?
C63 CO2 C55 119.09(10) . . ?
C57 CO2 C55 68.40(10) . . ?
C56 CO2 C55 40.74(10) . . ?
C64 CO2 C55 109.44(10) . . ?
C59 CO2 C55 40.51(11) . . ?
C62 CO2 C60 68.62(11) . . ?
C61 CO2 C60 40.86(10) . . ?
C63 CO2 C60 68.52(10) . . ?
C57 CO2 C60 118.91(10) . . ?
C56 CO2 C60 109.13(11) . . ?
C64 CO2 C60 40.93(10) . . ?
C59 CO2 C60 166.58(10) . . ?
C55 CO2 C60 129.31(11) . . ?
C62 CO2 C58 105.96(11) . . ?
C61 CO2 C58 117.07(10) . . ?
C63 CO2 C58 126.36(11) . . ?
C57 CO2 C58 40.76(10) . . ?
C56 CO2 C58 68.55(11) . . ?
C64 CO2 C58 164.78(11) . . ?
C59 CO2 C58 40.77(10) . . ?
C55 CO2 C58 68.28(10) . . ?
C60 CO2 C58 151.95(10) . . ?
N2 N1 C1 114.21(16) . . ?
N2 N1 B1 123.35(17) . . ?
C1 N1 B1 122.28(17) . . ?
C7 N2 N1 116.00(16) . . ?
C7 N3 N4 114.66(17) . . ?
N3 N4 C14 114.30(16) . . ?
N3 N4 B1 125.85(16) . . ?
C14 N4 B1 119.76(16) . . ?
N6 N5 C23 113.31(16) . . ?
N6 N5 B2 123.35(17) . . ?
C23 N5 B2 123.33(17) . . ?
C29 N6 N5 115.76(17) . . ?
C29 N7 N8 114.68(17) . . ?
N7 N8 C36 112.81(16) . . ?
N7 N8 B2 125.57(16) . . ?
C36 N8 B2 121.61(16) . . ?
C6 C1 C2 118.1(2) . . ?
C6 C1 N1 122.31(19) . . ?
C2 C1 N1 119.63(19) . . ?
C3 C2 C1 120.6(2) . . ?
C4 C3 C2 120.9(2) . . ?
C3 C4 C5 118.7(2) . . ?
C4 C5 C6 121.2(2) . . ?
C5 C6 C1 120.3(2) . . ?
N2 C7 N3 131.24(19) . . ?
N2 C7 C8 114.70(17) . . ?
N3 C7 C8 113.98(18) . . ?
C13 C8 C9 116.03(19) . . ?
C13 C8 C7 122.94(18) . . ?
C9 C8 C7 121.03(18) . . ?
F1 C9 C10 117.61(19) . . ?
F1 C9 C8 119.75(18) . . ?
C10 C9 C8 122.6(2) . . ?
F2 C10 C9 120.0(2) . . ?
F2 C10 C11 120.4(2) . . ?
C9 C10 C11 119.6(2) . . ?
F3 C11 C12 120.2(2) . . ?
F3 C11 C10 119.8(2) . . ?
C12 C11 C10 119.9(2) . . ?
F4 C12 C11 120.5(2) . . ?
F4 C12 C13 120.0(2) . . ?
C11 C12 C13 119.5(2) . . ?
F5 C13 C12 117.85(19) . . ?
F5 C13 C8 119.80(18) . . ?
C12 C13 C8 122.4(2) . . ?
C19 C14 C15 120.46(18) . . ?
C19 C14 N4 120.13(17) . . ?
C15 C14 N4 119.38(18) . . ?
C16 C15 C14 118.35(19) . . ?
C16 C15 C20 120.39(18) . . ?
C14 C15 C20 121.26(19) . . ?
C17 C16 C15 122.44(18) . . ?
C16 C17 C18 117.75(19) . . ?
C16 C17 C21 121.55(18) . . ?
C18 C17 C21 120.7(2) . . ?
C19 C18 C17 122.0(2) . . ?
C18 C19 C14 118.86(18) . . ?
C18 C19 C22 119.64(19) . . ?
C14 C19 C22 121.50(19) . . ?
C24 C23 C28 118.2(2) . . ?
C24 C23 N5 121.84(19) . . ?
C28 C23 N5 119.98(18) . . ?
C25 C24 C23 120.2(2) . . ?
C24 C25 C26 121.5(2) . . ?
C27 C26 C25 118.4(2) . . ?
C28 C27 C26 121.0(2) . . ?
C27 C28 C23 120.7(2) . . ?
N6 C29 N7 131.61(19) . . ?
N6 C29 C30 114.96(18) . . ?
N7 C29 C30 113.43(18) . . ?
C31 C30 C35 116.75(19) . . ?
C31 C30 C29 121.32(19) . . ?
C35 C30 C29 121.87(19) . . ?
F8 C31 C32 118.0(2) . . ?
F8 C31 C30 119.88(19) . . ?
C32 C31 C30 122.1(2) . . ?
F9 C32 C31 120.9(2) . . ?
F9 C32 C33 119.7(2) . . ?
C31 C32 C33 119.4(2) . . ?
F10 C33 C34 119.7(2) . . ?
F10 C33 C32 120.1(2) . . ?
C34 C33 C32 120.2(2) . . ?
F11 C34 C33 120.1(2) . . ?
F11 C34 C35 120.7(2) . . ?
C33 C34 C35 119.2(2) . . ?
F12 C35 C34 117.80(19) . . ?
F12 C35 C30 119.89(19) . . ?
C34 C35 C30 122.3(2) . . ?
C41 C36 C37 120.61(19) . . ?
C41 C36 N8 120.06(18) . . ?
C37 C36 N8 119.33(18) . . ?
C38 C37 C36 118.5(2) . . ?
C38 C37 C42 120.62(19) . . ?
C36 C37 C42 120.90(19) . . ?
C39 C38 C37 122.07(19) . . ?
C40 C39 C38 117.8(2) . . ?
C40 C39 C43 121.5(2) . . ?
C38 C39 C43 120.6(2) . . ?
C39 C40 C41 122.3(2) . . ?
C40 C41 C36 118.57(19) . . ?
C40 C41 C44 120.3(2) . . ?
C36 C41 C44 121.09(19) . . ?
C49 C45 C46 107.9(2) . . ?
C49 C45 CO1 69.37(13) . . ?
C46 C45 CO1 69.78(13) . . ?
C47 C46 C45 107.7(2) . . ?
C47 C46 CO1 69.62(13) . . ?
C45 C46 CO1 69.09(13) . . ?
C46 C47 C48 108.3(2) . . ?
C46 C47 CO1 69.80(13) . . ?
C48 C47 CO1 69.49(13) . . ?
C47 C48 C49 108.0(2) . . ?
C47 C48 CO1 69.78(13) . . ?
C49 C48 CO1 69.21(13) . . ?
C45 C49 C48 108.0(2) . . ?
C45 C49 CO1 69.79(13) . . ?
C48 C49 CO1 69.85(13) . . ?
C54 C50 C51 107.8(2) . . ?
C54 C50 CO1 69.48(13) . . ?
C51 C50 CO1 69.56(13) . . ?
C52 C51 C50 108.1(2) . . ?
C52 C51 CO1 69.67(13) . . ?
C50 C51 CO1 69.35(13) . . ?
C51 C52 C53 107.7(2) . . ?
C51 C52 CO1 69.57(13) . . ?
C53 C52 CO1 69.36(13) . . ?
C54 C53 C52 108.3(2) . . ?
C54 C53 CO1 69.54(13) . . ?
C52 C53 CO1 69.64(13) . . ?
C53 C54 C50 108.1(2) . . ?
C53 C54 CO1 69.69(13) . . ?
C50 C54 CO1 69.59(13) . . ?
C59 C55 C56 108.5(2) . . ?
C59 C55 CO2 69.74(14) . . ?
C56 C55 CO2 69.58(14) . . ?
C57 C56 C55 107.7(2) . . ?
C57 C56 CO2 69.60(14) . . ?
C55 C56 CO2 69.68(14) . . ?
C56 C57 C58 108.1(2) . . ?
C56 C57 CO2 69.67(13) . . ?
C58 C57 CO2 69.80(14) . . ?
C57 C58 C59 107.9(2) . . ?
C57 C58 CO2 69.44(13) . . ?
C59 C58 CO2 69.52(13) . . ?
C55 C59 C58 107.8(2) . . ?
C55 C59 CO2 69.75(14) . . ?
C58 C59 CO2 69.70(13) . . ?
C61 C60 C64 107.5(2) . . ?
C61 C60 CO2 69.19(13) . . ?
C64 C60 CO2 69.45(13) . . ?
C62 C61 C60 108.3(2) . . ?
C62 C61 CO2 69.63(14) . . ?
C60 C61 CO2 69.95(13) . . ?
C61 C62 C63 108.0(2) . . ?
C61 C62 CO2 69.73(15) . . ?
C63 C62 CO2 69.75(14) . . ?
C64 C63 C62 108.2(2) . . ?
C64 C63 CO2 69.90(14) . . ?
C62 C63 CO2 69.30(15) . . ?
C63 C64 C60 108.1(2) . . ?
C63 C64 CO2 69.66(14) . . ?
C60 C64 CO2 69.62(13) . . ?
F6 B1 F7 105.39(16) . . ?
F6 B1 N4 110.16(17) . . ?
F7 B1 N4 110.85(18) . . ?
F6 B1 N1 110.82(17) . . ?
F7 B1 N1 111.12(17) . . ?
N4 B1 N1 108.49(17) . . ?
F13 B2 F14 106.34(17) . . ?
F13 B2 N8 109.94(17) . . ?
F14 B2 N8 111.85(18) . . ?
F13 B2 N5 110.23(18) . . ?
F14 B2 N5 110.19(17) . . ?
N8 B2 N5 108.29(17) . . ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_Co-1j
_database_code_depnum_ccdc_archive 'CCDC 1471292'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C79 H92 B2 Co2 F4 N8'
_chemical_formula_weight         1369.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Co Co 0.3494 0.9721 '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                   11.6834(7)
_cell_length_b                   12.0343(7)
_cell_length_c                   16.1553(10)
_cell_angle_alpha                90.699(2)
_cell_angle_beta                 105.390(2)
_cell_angle_gamma                117.4381(17)
_cell_volume                     1919.5(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9958
_cell_measurement_theta_min      6.045
_cell_measurement_theta_max      54.55

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_F_000             722
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.488
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7002
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51822
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.332
_diffrn_reflns_theta_max         27.327
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8568
_reflns_number_gt                7022
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0421P)²+1.7212P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8568
_refine_ls_number_parameters     539
_refine_ls_number_restraints     175
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1_1 F 0.56282(11) 0.48560(10) 0.20801(8) 0.0307(3) Uani 1 1 d . . . . .
F2_1 F 0.73130(13) 0.56705(10) 0.14516(7) 0.0300(3) Uani 1 1 d . . . . .
N1_1 N 0.69116(15) 0.71337(13) 0.22032(9) 0.0189(3) Uani 1 1 d . . . . .
N2_1 N 0.76538(14) 0.80853(13) 0.28942(9) 0.0176(3) Uani 1 1 d . . . . .
N3_1 N 0.86490(14) 0.68868(13) 0.36806(9) 0.0161(3) Uani 1 1 d . . . . .
N4_1 N 0.79509(14) 0.59024(13) 0.30087(9) 0.0167(3) Uani 1 1 d . . . . .
C1_1 C 0.61527(18) 0.74330(17) 0.15024(11) 0.0208(4) Uani 1 1 d . . . . .
C2_1 C 0.5326(2) 0.65442(19) 0.07443(13) 0.0326(5) Uani 1 1 d . . . . .
H2_1 H 0.5268 0.5730 0.0711 0.039 Uiso 1 1 calc R U . . .
C3_1 C 0.4596(2) 0.6841(2) 0.00455(13) 0.0369(5) Uani 1 1 d . . . . .
H3_1 H 0.4058 0.6232 -0.0467 0.044 Uiso 1 1 calc R U . . .
C4_1 C 0.4634(3) 0.8003(2) 0.00774(14) 0.0418(6) Uani 1 1 d . . . . .
H4_1 H 0.4124 0.8198 -0.0404 0.050 Uiso 1 1 calc R U . . .
C5_1 C 0.5436(3) 0.8883(2) 0.08308(15) 0.0458(6) Uani 1 1 d . . . . .
H5_1 H 0.5470 0.9686 0.0865 0.055 Uiso 1 1 calc R U . . .
C6_1 C 0.6189(2) 0.86069(18) 0.15340(13) 0.0305(5) Uani 1 1 d . . . . .
H6_1 H 0.6735 0.9224 0.2042 0.037 Uiso 1 1 calc R U . . .
C7_1 C 0.84416(16) 0.78875(15) 0.35740(11) 0.0155(3) Uani 1 1 d . . . . .
C8_1 C 0.92344(16) 0.89639(15) 0.43071(11) 0.0153(3) Uani 1 1 d . . . . .
C9_1 C 0.91377(17) 1.00820(15) 0.42598(11) 0.0170(3) Uani 1 1 d . . . . .
H9_1 H 0.8546 1.0146 0.3754 0.020 Uiso 1 1 calc R U . . .
C10_1 C 1.01127(17) 0.89035(15) 0.50636(11) 0.0168(3) Uani 1 1 d . . . . .
H10_1 H 1.0197 0.8157 0.5115 0.020 Uiso 1 1 calc R U . . .
C11_1 C 0.83280(17) 0.49447(15) 0.31131(11) 0.0171(3) Uani 1 1 d . . . . .
C12_1 C 0.75982(19) 0.38095(16) 0.25139(12) 0.0221(4) Uani 1 1 d . . . . .
H12_1 H 0.6823 0.3672 0.2054 0.026 Uiso 1 1 calc R U . . .
C13_1 C 0.8009(2) 0.28910(17) 0.25938(12) 0.0260(4) Uani 1 1 d . . . . .
H13_1 H 0.7517 0.2138 0.2179 0.031 Uiso 1 1 calc R U . . .
C14_1 C 0.9123(2) 0.30503(17) 0.32685(13) 0.0262(4) Uani 1 1 d . . . . .
H14_1 H 0.9396 0.2416 0.3317 0.031 Uiso 1 1 calc R U . . .
C15_1 C 0.9828(2) 0.41570(17) 0.38690(12) 0.0240(4) Uani 1 1 d . . . . .
H15_1 H 1.0586 0.4275 0.4337 0.029 Uiso 1 1 calc R U . . .
C16_1 C 0.94447(18) 0.50948(16) 0.37969(11) 0.0193(3) Uani 1 1 d . . . . .
H16_1 H 0.9944 0.5845 0.4215 0.023 Uiso 1 1 calc R U . . .
B1_1 B 0.6921(2) 0.58580(18) 0.21706(13) 0.0201(4) Uani 1 1 d . . . . .
CO1_2 Co 1.5000 1.0000 0.5000 0.01618(9) Uani 1 2 d S . P . .
C1_2 C 1.33518(18) 1.02754(17) 0.48296(13) 0.0221(4) Uani 1 1 d . . . . .
C2_2 C 1.29342(17) 0.89633(17) 0.45954(12) 0.0205(4) Uani 1 1 d . . . . .
C3_2 C 1.34937(17) 0.85397(16) 0.53437(12) 0.0200(4) Uani 1 1 d . . . . .
C4_2 C 1.42625(18) 0.95957(17) 0.60375(12) 0.0220(4) Uani 1 1 d . . . . .
C5_2 C 1.41737(18) 1.06653(17) 0.57184(13) 0.0233(4) Uani 1 1 d . . . . .
C6_2 C 1.2937(2) 1.1072(2) 0.42494(16) 0.0340(5) Uani 1 1 d . . . . .
H6A_2 H 1.2063 1.0958 0.4279 0.051 Uiso 1 1 calc R U . . .
H6B_2 H 1.2854 1.0814 0.3650 0.051 Uiso 1 1 calc R U . . .
H6C_2 H 1.3622 1.1966 0.4440 0.051 Uiso 1 1 calc R U . . .
C7_2 C 1.20370(19) 0.81751(19) 0.37282(13) 0.0298(4) Uani 1 1 d . . . . .
H7A_2 H 1.1089 0.7886 0.3691 0.045 Uiso 1 1 calc R U . . .
H7B_2 H 1.2173 0.7439 0.3656 0.045 Uiso 1 1 calc R U . . .
H7C_2 H 1.2260 0.8683 0.3269 0.045 Uiso 1 1 calc R U . . .
C8_2 C 1.3296(2) 0.72259(17) 0.53974(14) 0.0274(4) Uani 1 1 d . . . . .
H8A_2 H 1.2500 0.6732 0.5589 0.041 Uiso 1 1 calc R U . . .
H8B_2 H 1.4099 0.7265 0.5815 0.041 Uiso 1 1 calc R U . . .
H8C_2 H 1.3159 0.6821 0.4824 0.041 Uiso 1 1 calc R U . . .
C9_2 C 1.4990(2) 0.9577(2) 0.69508(13) 0.0336(5) Uani 1 1 d . . . . .
H9A_2 H 1.4402 0.9437 0.7316 0.050 Uiso 1 1 calc R U . . .
H9B_2 H 1.5819 1.0391 0.7178 0.050 Uiso 1 1 calc R U . . .
H9C_2 H 1.5223 0.8893 0.6954 0.050 Uiso 1 1 calc R U . . .
C10_2 C 1.4797(2) 1.19550(19) 0.62365(16) 0.0349(5) Uani 1 1 d . . . . .
H10A_2 H 1.4176 1.1983 0.6531 0.052 Uiso 1 1 calc R U . . .
H10B_2 H 1.4972 1.2592 0.5847 0.052 Uiso 1 1 calc R U . . .
H10C_2 H 1.5652 1.2134 0.6670 0.052 Uiso 1 1 calc R U . . .
CO1_3 Co 1.0000 1.0000 0.0000 0.03814(12) Uani 1 2 d S . P . .
C1A_3 C 0.8513(9) 1.0266(8) 0.0364(6) 0.0455(16) Uani 0.5 1 d . . P A 1
C2A_3 C 0.7935(7) 0.9191(10) -0.0271(5) 0.0407(16) Uani 0.5 1 d . . P A 1
C3A_3 C 0.8353(11) 0.8300(12) 0.0105(10) 0.032(2) Uani 0.5 1 d . . P A 1
C4A_3 C 0.925(3) 0.8907(15) 0.0945(13) 0.032(2) Uani 0.5 1 d . . P A 1
C5A_3 C 0.9295(10) 1.0087(8) 0.1116(4) 0.0370(16) Uani 0.5 1 d . . P A 1
C6A_3 C 0.8244(9) 1.1391(8) 0.0258(7) 0.094(2) Uani 0.5 1 d . . P A 1
H6AA_3 H 0.7438 1.1217 0.0426 0.141 Uiso 0.5 1 calc R U P A 1
H6AB_3 H 0.8095 1.1524 -0.0351 0.141 Uiso 0.5 1 calc R U P A 1
H6AC_3 H 0.9026 1.2154 0.0629 0.141 Uiso 0.5 1 calc R U P A 1
C7A_3 C 0.6955(6) 0.8907(8) -0.1180(4) 0.0729(18) Uani 0.5 1 d . . P A 1
H7AA_3 H 0.6023 0.8469 -0.1156 0.109 Uiso 0.5 1 calc R U P A 1
H7AB_3 H 0.7084 0.8366 -0.1564 0.109 Uiso 0.5 1 calc R U P A 1
H7AC_3 H 0.7128 0.9703 -0.1406 0.109 Uiso 0.5 1 calc R U P A 1
C8A_3 C 0.7969(8) 0.7018(6) -0.0307(5) 0.0604(16) Uani 0.5 1 d . . P A 1
H8AA_3 H 0.7178 0.6384 -0.0162 0.091 Uiso 0.5 1 calc R U P A 1
H8AB_3 H 0.8727 0.6843 -0.0092 0.091 Uiso 0.5 1 calc R U P A 1
H8AC_3 H 0.7747 0.6981 -0.0939 0.091 Uiso 0.5 1 calc R U P A 1
C9A_3 C 0.9920(10) 0.8346(7) 0.1624(7) 0.0568(19) Uani 0.5 1 d . . P A 1
H9AA_3 H 0.9388 0.8019 0.2027 0.085 Uiso 0.5 1 calc R U P A 1
H9AB_3 H 1.0838 0.9005 0.1947 0.085 Uiso 0.5 1 calc R U P A 1
H9AC_3 H 0.9965 0.7654 0.1335 0.085 Uiso 0.5 1 calc R U P A 1
C10A_3 C 1.0023(9) 1.0968(8) 0.1990(6) 0.086(2) Uani 0.5 1 d . . P A 1
H10D_3 H 0.9420 1.0712 0.2355 0.129 Uiso 0.5 1 calc R U P A 1
H10E_3 H 1.0272 1.1842 0.1895 0.129 Uiso 0.5 1 calc R U P A 1
H10F_3 H 1.0842 1.0914 0.2282 0.129 Uiso 0.5 1 calc R U P A 1
C1B_3 C 0.8229(7) 0.9921(9) -0.0097(7) 0.0486(17) Uani 0.5 1 d . . P A 2
C2B_3 C 0.7977(7) 0.8735(7) -0.0487(4) 0.0403(16) Uani 0.5 1 d . . P A 2
C3B_3 C 0.8708(11) 0.8275(14) 0.0123(10) 0.036(2) Uani 0.5 1 d . . P A 2
C4B_3 C 0.936(2) 0.9161(16) 0.0931(11) 0.041(3) Uani 0.5 1 d . . P A 2
C5B_3 C 0.9092(10) 1.0192(10) 0.0764(7) 0.054(2) Uani 0.5 1 d . . P A 2
C6B_3 C 0.7655(9) 1.0751(8) -0.0520(7) 0.094(2) Uani 0.5 1 d . . P A 2
H6BA_3 H 0.6833 1.0569 -0.0369 0.141 Uiso 0.5 1 calc R U P A 2
H6BB_3 H 0.7432 1.0574 -0.1153 0.141 Uiso 0.5 1 calc R U P A 2
H6BC_3 H 0.8327 1.1646 -0.0312 0.141 Uiso 0.5 1 calc R U P A 2
C7B_3 C 0.7080(6) 0.8037(8) -0.1399(4) 0.0729(18) Uani 0.5 1 d . . P A 2
H7BA_3 H 0.6169 0.7442 -0.1382 0.109 Uiso 0.5 1 calc R U P A 2
H7BB_3 H 0.7463 0.7569 -0.1622 0.109 Uiso 0.5 1 calc R U P A 2
H7BC_3 H 0.7030 0.8650 -0.1781 0.109 Uiso 0.5 1 calc R U P A 2
C8B_3 C 0.8683(8) 0.7004(6) -0.0007(5) 0.0604(16) Uani 0.5 1 d . . P A 2
H8BA_3 H 0.7857 0.6329 0.0078 0.091 Uiso 0.5 1 calc R U P A 2
H8BB_3 H 0.9477 0.7034 0.0416 0.091 Uiso 0.5 1 calc R U P A 2
H8BC_3 H 0.8699 0.6833 -0.0597 0.091 Uiso 0.5 1 calc R U P A 2
C9B_3 C 1.0181(10) 0.8952(7) 0.1746(7) 0.0568(19) Uani 0.5 1 d . . P A 2
H9BA_3 H 0.9576 0.8417 0.2064 0.085 Uiso 0.5 1 calc R U P A 2
H9BB_3 H 1.0841 0.9771 0.2113 0.085 Uiso 0.5 1 calc R U P A 2
H9BC_3 H 1.0658 0.8533 0.1589 0.085 Uiso 0.5 1 calc R U P A 2
C10B_3 C 0.9543(9) 1.1260(8) 0.1464(6) 0.086(2) Uani 0.5 1 d . . P A 2
H10A_3 H 0.8891 1.1011 0.1793 0.129 Uiso 0.5 1 calc R U P A 2
H10B_3 H 0.9598 1.2006 0.1203 0.129 Uiso 0.5 1 calc R U P A 2
H10C_3 H 1.0436 1.1463 0.1857 0.129 Uiso 0.5 1 calc R U P A 2
C1_4 C 0.6994(8) 0.5970(7) 0.6438(7) 0.089(3) Uani 0.5 1 d . . P B -1
H1A_4 H 0.6666 0.5997 0.6933 0.133 Uiso 0.5 1 calc R U P B -1
H1B_4 H 0.7637 0.6832 0.6391 0.133 Uiso 0.5 1 calc R U P B -1
H1C_4 H 0.7444 0.5448 0.6524 0.133 Uiso 0.5 1 calc R U P B -1
C2B_4 C 0.4984(16) 0.4923(16) 0.4068(9) 0.079(4) Uani 0.5 1 d . . P B -1
H2B_4 H 0.5143 0.4971 0.3519 0.095 Uiso 0.5 1 calc R U P B -1
C2A_4 C 0.4531(10) 0.4866(14) 0.5671(8) 0.043(2) Uani 0.5 1 d . . P B -1
H2A_4 H 0.4380 0.4887 0.6219 0.052 Uiso 0.5 1 calc R U P B -1
C3B_4 C 0.6034(12) 0.5414(13) 0.4833(11) 0.069(4) Uani 0.5 1 d . . P B -1
H3B_4 H 0.6937 0.5768 0.4810 0.083 Uiso 0.5 1 calc R U P B -1
C3A_4 C 0.3453(11) 0.4291(13) 0.4929(7) 0.047(2) Uani 0.5 1 d . . P B -1
H3A_4 H 0.2558 0.3854 0.4967 0.056 Uiso 0.5 1 calc R U P B -1
C4B_4 C 0.3663(14) 0.4346(13) 0.4135(7) 0.065(3) Uani 0.5 1 d . . P B -1
H4B_4 H 0.2909 0.3990 0.3623 0.078 Uiso 0.5 1 calc R U P B -1
C4A_4 C 0.5823(9) 0.5411(13) 0.5621(8) 0.054(2) Uani 0.5 1 d . . P B -1


_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
F1_1 B1_1 1.399(2) . ?
F2_1 B1_1 1.407(2) . ?
N1_1 N2_1 1.3599(19) . ?
N1_1 C1_1 1.403(2) . ?
N1_1 B1_1 1.541(2) . ?
N2_1 C7_1 1.335(2) . ?
N3_1 C7_1 1.338(2) . ?
N3_1 N4_1 1.3620(18) . ?
N4_1 C11_1 1.409(2) . ?
N4_1 B1_1 1.536(2) . ?
C1_1 C6_1 1.393(3) . ?
C1_1 C2_1 1.402(2) . ?
C2_1 C3_1 1.381(3) . ?
C3_1 C4_1 1.379(3) . ?
C4_1 C5_1 1.389(3) . ?
C5_1 C6_1 1.387(3) . ?
C7_1 C8_1 1.488(2) . ?
C8_1 C10_1 1.399(2) . ?
C8_1 C9_1 1.403(2) . ?
C9_1 C10_1 1.388(2) 2_776 ?
C10_1 C9_1 1.388(2) 2_776 ?
C11_1 C16_1 1.403(2) . ?
C11_1 C12_1 1.410(2) . ?
C12_1 C13_1 1.388(3) . ?
C13_1 C14_1 1.390(3) . ?
C14_1 C15_1 1.388(3) . ?
C15_1 C16_1 1.389(2) . ?
CO1_2 C2_2 2.0437(17) 2_876 ?
CO1_2 C2_2 2.0437(17) . ?
CO1_2 C3_2 2.0460(17) . ?
CO1_2 C3_2 2.0460(17) 2_876 ?
CO1_2 C4_2 2.0466(18) . ?
CO1_2 C4_2 2.0467(18) 2_876 ?
CO1_2 C1_2 2.0501(17) 2_876 ?
CO1_2 C1_2 2.0501(17) . ?
CO1_2 C5_2 2.0504(18) . ?
CO1_2 C5_2 2.0505(18) 2_876 ?
C1_2 C5_2 1.428(3) . ?
C1_2 C2_2 1.432(2) . ?
C1_2 C6_2 1.498(3) . ?
C2_2 C3_2 1.432(3) . ?
C2_2 C7_2 1.494(3) . ?
C3_2 C4_2 1.434(3) . ?
C3_2 C8_2 1.496(2) . ?
C4_2 C5_2 1.430(3) . ?
C4_2 C9_2 1.501(3) . ?
C5_2 C10_2 1.498(3) . ?
CO1_3 C5B_3 1.902(10) 2_775 ?
CO1_3 C5B_3 1.902(10) . ?
CO1_3 C4B_3 1.94(2) . ?
CO1_3 C4B_3 1.94(2) 2_775 ?
CO1_3 C3B_3 1.977(14) . ?
CO1_3 C3B_3 1.977(14) 2_775 ?
CO1_3 C1B_3 1.990(7) . ?
CO1_3 C1B_3 1.990(7) 2_775 ?
CO1_3 C2B_3 2.047(7) . ?
CO1_3 C2B_3 2.047(7) 2_775 ?
CO1_3 C2A_3 2.056(7) . ?
CO1_3 C2A_3 2.056(7) 2_775 ?
C1A_3a C5A_3 1.398(10) . ?
C1A_3a C2A_3 1.406(11) . ?
C1A_3a C6A_3 1.527(10) . ?
C2A_3a C3A_3 1.449(13) . ?
C2A_3a C7A_3 1.523(9) . ?
C3A_3a C4A_3 1.41(2) . ?
C3A_3a C8A_3 1.483(15) . ?
C4A_3a C5A_3 1.417(15) . ?
C4A_3a C9A_3 1.52(2) . ?
C5A_3a C10A_3 1.529(10) . ?
C1B_3b C5B_3 1.414(11) . ?
C1B_3b C2B_3 1.419(10) . ?
C1B_3b C6B_3 1.519(11) . ?
C2B_3b C3B_3 1.417(14) . ?
C2B_3b C7B_3 1.521(9) . ?
C3B_3b C4B_3 1.45(2) . ?
C3B_3b C8B_3 1.527(15) . ?
C4B_3b C5B_3 1.425(19) . ?
C4B_3b C9B_3 1.51(2) . ?
C5B_3b C10B_3 1.495(10) . ?
C1_4 C4A_4 1.495(11) . ?
C2B_4 C3B_4 1.376(16) . ?
C2B_4 C4B_4 1.407(17) . ?
C2A_4 C4A_4 1.367(13) . ?
C2A_4 C3A_4 1.369(12) . ?
C3B_4 C4A_4 1.36(2) . ?
C3A_4 C4B_4 1.365(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2_1 N1_1 C1_1 113.54(13) . . ?
N2_1 N1_1 B1_1 123.92(14) . . ?
C1_1 N1_1 B1_1 122.52(14) . . ?
C7_1 N2_1 N1_1 116.98(14) . . ?
C7_1 N3_1 N4_1 116.57(14) . . ?
N3_1 N4_1 C11_1 114.01(13) . . ?
N3_1 N4_1 B1_1 124.26(13) . . ?
C11_1 N4_1 B1_1 121.55(13) . . ?
C6_1 C1_1 C2_1 117.99(17) . . ?
C6_1 C1_1 N1_1 121.70(16) . . ?
C2_1 C1_1 N1_1 120.32(16) . . ?
C3_1 C2_1 C1_1 120.65(18) . . ?
C4_1 C3_1 C2_1 121.29(19) . . ?
C3_1 C4_1 C5_1 118.40(19) . . ?
C6_1 C5_1 C4_1 121.05(19) . . ?
C5_1 C6_1 C1_1 120.61(18) . . ?
N2_1 C7_1 N3_1 129.66(15) . . ?
N2_1 C7_1 C8_1 114.52(14) . . ?
N3_1 C7_1 C8_1 115.78(14) . . ?
C10_1 C8_1 C9_1 117.62(15) . . ?
C10_1 C8_1 C7_1 121.30(15) . . ?
C9_1 C8_1 C7_1 121.07(15) . . ?
C10_1 C9_1 C8_1 121.41(16) 2_776 . ?
C9_1 C10_1 C8_1 120.96(15) 2_776 . ?
C16_1 C11_1 N4_1 121.65(14) . . ?
C16_1 C11_1 C12_1 118.07(16) . . ?
N4_1 C11_1 C12_1 120.26(16) . . ?
C13_1 C12_1 C11_1 120.23(17) . . ?
C12_1 C13_1 C14_1 121.40(17) . . ?
C15_1 C14_1 C13_1 118.48(17) . . ?
C14_1 C15_1 C16_1 121.13(18) . . ?
C15_1 C16_1 C11_1 120.67(16) . . ?
F1_1 B1_1 F2_1 108.28(14) . . ?
F1_1 B1_1 N4_1 110.85(15) . . ?
F2_1 B1_1 N4_1 109.15(15) . . ?
F1_1 B1_1 N1_1 110.52(15) . . ?
F2_1 B1_1 N1_1 109.56(15) . . ?
N4_1 B1_1 N1_1 108.46(13) . . ?
C2_2 CO1_2 C2_2 180.0 2_876 . ?
C2_2 CO1_2 C3_2 139.00(7) 2_876 . ?
C2_2 CO1_2 C3_2 41.00(7) . . ?
C2_2 CO1_2 C3_2 41.00(7) 2_876 2_876 ?
C2_2 CO1_2 C3_2 139.00(7) . 2_876 ?
C3_2 CO1_2 C3_2 180.00(9) . 2_876 ?
C2_2 CO1_2 C4_2 111.02(7) 2_876 . ?
C2_2 CO1_2 C4_2 68.98(7) . . ?
C3_2 CO1_2 C4_2 41.03(7) . . ?
C3_2 CO1_2 C4_2 138.97(7) 2_876 . ?
C2_2 CO1_2 C4_2 68.98(7) 2_876 2_876 ?
C2_2 CO1_2 C4_2 111.02(7) . 2_876 ?
C3_2 CO1_2 C4_2 138.97(7) . 2_876 ?
C3_2 CO1_2 C4_2 41.03(7) 2_876 2_876 ?
C4_2 CO1_2 C4_2 180.0 . 2_876 ?
C2_2 CO1_2 C1_2 40.96(7) 2_876 2_876 ?
C2_2 CO1_2 C1_2 139.04(7) . 2_876 ?
C3_2 CO1_2 C1_2 111.10(7) . 2_876 ?
C3_2 CO1_2 C1_2 68.90(7) 2_876 2_876 ?
C4_2 CO1_2 C1_2 111.26(7) . 2_876 ?
C4_2 CO1_2 C1_2 68.74(7) 2_876 2_876 ?
C2_2 CO1_2 C1_2 139.04(7) 2_876 . ?
C2_2 CO1_2 C1_2 40.96(7) . . ?
C3_2 CO1_2 C1_2 68.90(7) . . ?
C3_2 CO1_2 C1_2 111.10(7) 2_876 . ?
C4_2 CO1_2 C1_2 68.74(7) . . ?
C4_2 CO1_2 C1_2 111.26(7) 2_876 . ?
C1_2 CO1_2 C1_2 180.0 2_876 . ?
C2_2 CO1_2 C5_2 111.09(7) 2_876 . ?
C2_2 CO1_2 C5_2 68.91(7) . . ?
C3_2 CO1_2 C5_2 68.94(7) . . ?
C3_2 CO1_2 C5_2 111.06(7) 2_876 . ?
C4_2 CO1_2 C5_2 40.85(7) . . ?
C4_2 CO1_2 C5_2 139.15(7) 2_876 . ?
C1_2 CO1_2 C5_2 139.23(8) 2_876 . ?
C1_2 CO1_2 C5_2 40.77(8) . . ?
C2_2 CO1_2 C5_2 68.91(7) 2_876 2_876 ?
C2_2 CO1_2 C5_2 111.09(7) . 2_876 ?
C3_2 CO1_2 C5_2 111.06(7) . 2_876 ?
C3_2 CO1_2 C5_2 68.94(7) 2_876 2_876 ?
C4_2 CO1_2 C5_2 139.15(7) . 2_876 ?
C4_2 CO1_2 C5_2 40.85(7) 2_876 2_876 ?
C1_2 CO1_2 C5_2 40.77(8) 2_876 2_876 ?
C1_2 CO1_2 C5_2 139.23(8) . 2_876 ?
C5_2 CO1_2 C5_2 180.00(8) . 2_876 ?
C5_2 C1_2 C2_2 108.12(16) . . ?
C5_2 C1_2 C6_2 126.38(18) . . ?
C2_2 C1_2 C6_2 125.44(18) . . ?
C5_2 C1_2 CO1_2 69.62(10) . . ?
C2_2 C1_2 CO1_2 69.28(10) . . ?
C6_2 C1_2 CO1_2 128.89(13) . . ?
C3_2 C2_2 C1_2 107.96(16) . . ?
C3_2 C2_2 C7_2 126.44(17) . . ?
C1_2 C2_2 C7_2 125.58(17) . . ?
C3_2 C2_2 CO1_2 69.59(10) . . ?
C1_2 C2_2 CO1_2 69.76(10) . . ?
C7_2 C2_2 CO1_2 127.61(13) . . ?
C2_2 C3_2 C4_2 107.80(15) . . ?
C2_2 C3_2 C8_2 126.17(17) . . ?
C4_2 C3_2 C8_2 126.02(17) . . ?
C2_2 C3_2 CO1_2 69.41(10) . . ?
C4_2 C3_2 CO1_2 69.51(10) . . ?
C8_2 C3_2 CO1_2 127.23(13) . . ?
C5_2 C4_2 C3_2 108.09(16) . . ?
C5_2 C4_2 C9_2 125.59(18) . . ?
C3_2 C4_2 C9_2 126.28(17) . . ?
C5_2 C4_2 CO1_2 69.72(10) . . ?
C3_2 C4_2 CO1_2 69.47(10) . . ?
C9_2 C4_2 CO1_2 128.27(13) . . ?
C1_2 C5_2 C4_2 108.02(16) . . ?
C1_2 C5_2 C10_2 126.17(18) . . ?
C4_2 C5_2 C10_2 125.78(19) . . ?
C1_2 C5_2 CO1_2 69.60(10) . . ?
C4_2 C5_2 CO1_2 69.43(10) . . ?
C10_2 C5_2 CO1_2 128.03(13) . . ?
C5B_3b CO1_3 C5B_3 180.0 2_775 . ?
C5B_3b CO1_3 C4B_3 136.5(6) 2_775 . ?
C5B_3b CO1_3 C4B_3 43.5(6) . . ?
C5B_3b CO1_3 C4B_3 43.5(6) 2_775 2_775 ?
C5B_3b CO1_3 C4B_3 136.5(6) . 2_775 ?
C4B_3b CO1_3 C4B_3 180.0 . 2_775 ?
C5B_3b CO1_3 C3B_3 106.9(5) 2_775 . ?
C5B_3b CO1_3 C3B_3 73.1(5) . . ?
C4B_3b CO1_3 C3B_3 43.5(6) . . ?
C4B_3b CO1_3 C3B_3 136.5(6) 2_775 . ?
C5B_3b CO1_3 C3B_3 73.1(5) 2_775 2_775 ?
C5B_3b CO1_3 C3B_3 106.9(5) . 2_775 ?
C4B_3b CO1_3 C3B_3 136.5(6) . 2_775 ?
C4B_3b CO1_3 C3B_3 43.5(6) 2_775 2_775 ?
C3B_3b CO1_3 C3B_3 180.0 . 2_775 ?
C5B_3b CO1_3 C1B_3 137.5(3) 2_775 . ?
C5B_3b CO1_3 C1B_3 42.5(3) . . ?
C4B_3b CO1_3 C1B_3 71.8(7) . . ?
C4B_3b CO1_3 C1B_3 108.2(7) 2_775 . ?
C3B_3b CO1_3 C1B_3 70.9(4) . . ?
C3B_3b CO1_3 C1B_3 109.1(4) 2_775 . ?
C5B_3b CO1_3 C1B_3 42.5(3) 2_775 2_775 ?
C5B_3b CO1_3 C1B_3 137.5(3) . 2_775 ?
C4B_3b CO1_3 C1B_3 108.2(7) . 2_775 ?
C4B_3b CO1_3 C1B_3 71.8(7) 2_775 2_775 ?
C3B_3b CO1_3 C1B_3 109.1(4) . 2_775 ?
C3B_3b CO1_3 C1B_3 70.9(4) 2_775 2_775 ?
C1B_3b CO1_3 C1B_3 180.0 . 2_775 ?
C5B_3b CO1_3 C2B_3 109.0(3) 2_775 . ?
C5B_3b CO1_3 C2B_3 71.0(3) . . ?
C4B_3b CO1_3 C2B_3 70.9(6) . . ?
C4B_3b CO1_3 C2B_3 109.1(6) 2_775 . ?
C3B_3b CO1_3 C2B_3 41.2(4) . . ?
C3B_3b CO1_3 C2B_3 138.8(4) 2_775 . ?
C1B_3b CO1_3 C2B_3 41.1(3) . . ?
C1B_3b CO1_3 C2B_3 138.9(3) 2_775 . ?
C5B_3b CO1_3 C2B_3 71.0(3) 2_775 2_775 ?
C5B_3b CO1_3 C2B_3 109.0(3) . 2_775 ?
C4B_3b CO1_3 C2B_3 109.1(6) . 2_775 ?
C4B_3b CO1_3 C2B_3 70.9(6) 2_775 2_775 ?
C3B_3b CO1_3 C2B_3 138.8(4) . 2_775 ?
C3B_3b CO1_3 C2B_3 41.2(4) 2_775 2_775 ?
C1B_3b CO1_3 C2B_3 138.9(3) . 2_775 ?
C1B_3b CO1_3 C2B_3 41.1(3) 2_775 2_775 ?
C2B_3b CO1_3 C2B_3 180.0 . 2_775 ?
C2A_3a CO1_3 C2A_3 180.0 . 2_775 ?
C5A_3a C1A_3a C2A_3 108.6(7) . . ?
C5A_3a C1A_3a C6A_3 126.3(9) . . ?
C2A_3a C1A_3a C6A_3 125.0(9) . . ?
C5A_3a C1A_3a CO1_3 73.7(5) . . ?
C2A_3a C1A_3a CO1_3 67.7(4) . . ?
C6A_3a C1A_3a CO1_3 127.4(5) . . ?
C1A_3a C2A_3a C3A_3 108.0(8) . . ?
C1A_3a C2A_3a C7A_3 128.5(8) . . ?
C3A_3a C2A_3a C7A_3 123.4(10) . . ?
C1A_3a C2A_3a CO1_3 73.0(4) . . ?
C3A_3a C2A_3a CO1_3 71.9(5) . . ?
C7A_3a C2A_3a CO1_3 124.0(5) . . ?
C4A_3a C3A_3a C2A_3 106.2(11) . . ?
C4A_3a C3A_3a C8A_3 125.9(11) . . ?
C2A_3a C3A_3a C8A_3 127.8(12) . . ?
C4A_3a C3A_3a CO1_3 71.1(10) . . ?
C2A_3a C3A_3a CO1_3 67.5(6) . . ?
C8A_3a C3A_3a CO1_3 124.7(8) . . ?
C3A_3a C4A_3a C5A_3 108.8(13) . . ?
C3A_3a C4A_3a C9A_3 126.9(12) . . ?
C5A_3a C4A_3a C9A_3 123.7(14) . . ?
C3A_3a C4A_3a CO1_3 70.1(9) . . ?
C5A_3a C4A_3a CO1_3 73.3(7) . . ?
C9A_3a C4A_3a CO1_3 129.1(16) . . ?
C1A_3a C5A_3a C4A_3 108.1(10) . . ?
C1A_3a C5A_3a C10A_3 126.6(8) . . ?
C4A_3a C5A_3a C10A_3 125.2(10) . . ?
C1A_3a C5A_3a CO1_3 68.5(4) . . ?
C4A_3a C5A_3a CO1_3 68.4(9) . . ?
C10A_3a C5A_3a CO1_3 130.9(7) . . ?
C5B_3b C1B_3b C2B_3 108.2(7) . . ?
C5B_3b C1B_3b C6B_3 125.6(10) . . ?
C2B_3b C1B_3b C6B_3 126.2(9) . . ?
C5B_3b C1B_3b CO1_3 65.4(5) . . ?
C2B_3b C1B_3b CO1_3 71.6(5) . . ?
C6B_3b C1B_3b CO1_3 129.5(6) . . ?
C3B_3b C2B_3b C1B_3 108.5(9) . . ?
C3B_3b C2B_3b C7B_3 124.2(9) . . ?
C1B_3b C2B_3b C7B_3 127.4(8) . . ?
C3B_3b C2B_3b CO1_3 66.7(6) . . ?
C1B_3b C2B_3b CO1_3 67.3(4) . . ?
C7B_3b C2B_3b CO1_3 132.1(5) . . ?
C2B_3b C3B_3b C4B_3 107.6(12) . . ?
C2B_3b C3B_3b C8B_3 126.3(11) . . ?
C4B_3b C3B_3b C8B_3 125.7(12) . . ?
C2B_3b C3B_3b CO1_3 72.1(6) . . ?
C4B_3b C3B_3b CO1_3 67.1(10) . . ?
C8B_3b C3B_3b CO1_3 131.5(7) . . ?
C5B_3b C4B_3b C3B_3 106.7(13) . . ?
C5B_3b C4B_3b C9B_3 130.5(13) . . ?
C3B_3b C4B_3b C9B_3 122.8(13) . . ?
C5B_3b C4B_3b CO1_3 66.7(8) . . ?
C3B_3b C4B_3b CO1_3 69.4(10) . . ?
C9B_3b C4B_3b CO1_3 127.2(15) . . ?
C1B_3b C5B_3b C4B_3 108.8(10) . . ?
C1B_3b C5B_3b C10B_3 128.8(10) . . ?
C4B_3b C5B_3b C10B_3 121.9(11) . . ?
C1B_3b C5B_3b CO1_3 72.1(5) . . ?
C4B_3b C5B_3b CO1_3 69.9(10) . . ?
C10B_3b C5B_3b CO1_3 130.1(8) . . ?
C3B_4 C2B_4 C4B_4 116.9(12) . . ?
C4A_4 C2A_4 C3A_4 120.0(12) . . ?
C4A_4 C3B_4 C2B_4 122.1(12) . . ?
C4B_4 C3A_4 C2A_4 120.1(13) . . ?
C3A_4 C4B_4 C2B_4 120.8(10) . . ?
C3B_4 C4A_4 C2A_4 119.9(9) . . ?
C3B_4 C4A_4 C1_4 120.5(10) . . ?
C2A_4 C4A_4 C1_4 119.6(10) . . ?

_refine_diff_density_max         0.454
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_1i
_database_code_depnum_ccdc_archive 'CCDC 1471293'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 B F2 N5'
_chemical_formula_sum            'C20 H22 B F2 N5'
_chemical_formula_weight         381.23

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   5.9716(2)
_cell_length_b                   17.0399(6)
_cell_length_c                   18.8991(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1923.09(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9954
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      27.11

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9382
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29576
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.219
_diffrn_reflns_theta_max         27.145
_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             2201
_reflns_number_gt                1796
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0395P)²+1.1881P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2201
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.07168(17) 0.17768(6) 0.56837(5) 0.0133(2) Uani 1 1 d . . . . .
N2 N 0.21027(17) 0.17921(6) 0.51582(5) 0.0143(2) Uani 1 1 d . . . . .
N3 N 0.5351(3) 0.2500 0.38281(10) 0.0293(4) Uani 1 2 d S T P . .
C11 C 0.4149(3) 0.2500 0.43014(10) 0.0194(4) Uani 1 2 d S T P . .
C5 C 0.1682(2) 0.00153(8) 0.67957(7) 0.0178(3) Uani 1 1 d . . . . .
H5 H 0.2681 -0.0160 0.7154 0.021 Uiso 1 1 calc R U . . .
C1 C 0.0445(2) 0.10003(7) 0.59923(6) 0.0140(3) Uani 1 1 d . . . . .
C7 C -0.2801(2) 0.07526(8) 0.51416(7) 0.0181(3) Uani 1 1 d . . . . .
H7A H -0.2203 0.1220 0.4905 0.027 Uiso 1 1 calc R U . . .
H7B H -0.4285 0.0871 0.5336 0.027 Uiso 1 1 calc R U . . .
H7C H -0.2922 0.0322 0.4800 0.027 Uiso 1 1 calc R U . . .
C2 C -0.1250(2) 0.05147(7) 0.57334(7) 0.0154(3) Uani 1 1 d . . . . .
C10 C 0.2608(3) 0.2500 0.48881(9) 0.0147(4) Uani 1 2 d S T P . .
C6 C 0.1931(2) 0.07704(8) 0.65256(6) 0.0158(3) Uani 1 1 d . . . . .
C3 C -0.1443(2) -0.02298(8) 0.60363(7) 0.0172(3) Uani 1 1 d . . . . .
H3 H -0.2609 -0.0567 0.5880 0.021 Uiso 1 1 calc R U . . .
C4 C 0.0010(2) -0.04925(8) 0.65575(7) 0.0181(3) Uani 1 1 d . . . . .
C9 C 0.3722(2) 0.13106(8) 0.68068(7) 0.0208(3) Uani 1 1 d . . . . .
H9A H 0.4470 0.1574 0.6411 0.031 Uiso 1 1 calc R U . . .
H9B H 0.4822 0.1005 0.7075 0.031 Uiso 1 1 calc R U . . .
H9C H 0.3039 0.1704 0.7117 0.031 Uiso 1 1 calc R U . . .
C8 C -0.0152(3) -0.13182(8) 0.68442(8) 0.0243(3) Uani 1 1 d . . . . .
H8A H -0.1612 -0.1542 0.6720 0.036 Uiso 1 1 calc R U . . .
H8B H 0.0012 -0.1308 0.7360 0.036 Uiso 1 1 calc R U . . .
H8C H 0.1040 -0.1641 0.6638 0.036 Uiso 1 1 calc R U . . .
B1 B -0.0649(4) 0.2500 0.59585(11) 0.0151(4) Uani 1 2 d S T P . .
F1 F -0.27483(18) 0.2500 0.56565(6) 0.0218(3) Uani 1 2 d S T P . .
F2 F -0.0747(2) 0.2500 0.66796(6) 0.0234(3) Uani 1 2 d S T P . .


_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 N2 1.2931(15) . ?
N1 C1 1.4551(15) . ?
N1 B1 1.5665(16) . ?
N2 C10 1.3442(13) . ?
N3 C11 1.147(3) . ?
C11 C10 1.441(3) . ?
C5 C6 1.3923(18) . ?
C5 C4 1.3955(19) . ?
C1 C2 1.3958(18) . ?
C1 C6 1.3988(18) . ?
C7 C2 1.5074(18) . ?
C2 C3 1.3966(18) . ?
C10 N2 1.3442(13) 7_565 ?
C6 C9 1.5081(18) . ?
C3 C4 1.3872(19) . ?
C4 C8 1.5108(18) . ?
B1 F2 1.364(2) . ?
B1 F1 1.377(2) . ?
B1 N1 1.5665(16) 7_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 113.43(10) . . ?
N2 N1 B1 124.90(11) . . ?
C1 N1 B1 121.62(10) . . ?
N1 N2 C10 116.97(11) . . ?
N3 C11 C10 179.1(2) . . ?
C6 C5 C4 122.08(12) . . ?
C2 C1 C6 123.13(12) . . ?
C2 C1 N1 118.65(11) . . ?
C6 C1 N1 118.20(11) . . ?
C1 C2 C3 117.05(12) . . ?
C1 C2 C7 123.09(11) . . ?
C3 C2 C7 119.84(12) . . ?
N2 C10 N2 127.64(16) 7_565 . ?
N2 C10 C11 115.83(8) 7_565 . ?
N2 C10 C11 115.83(8) . . ?
C5 C6 C1 117.08(12) . . ?
C5 C6 C9 120.70(12) . . ?
C1 C6 C9 122.21(12) . . ?
C4 C3 C2 122.17(12) . . ?
C3 C4 C5 118.47(12) . . ?
C3 C4 C8 120.99(12) . . ?
C5 C4 C8 120.50(12) . . ?
F2 B1 F1 112.02(16) . . ?
F2 B1 N1 110.70(11) . 7_565 ?
F1 B1 N1 109.67(10) . 7_565 ?
F2 B1 N1 110.70(11) . . ?
F1 B1 N1 109.67(10) . . ?
N1 B1 N1 103.75(14) 7_565 . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.044

_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_1h-BCF
_database_code_depnum_ccdc_archive 'CCDC 1471295'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C71 H28 B4 F34 N10'
_chemical_formula_weight         1710.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   32.728(4)
_cell_length_b                   8.7616(11)
_cell_length_c                   29.466(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.024(3)
_cell_angle_gamma                90
_cell_volume                     7833.0(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      25.18

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             3400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.143
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6486
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67066
_diffrn_reflns_av_unetI/netI     0.0793
_diffrn_reflns_av_R_equivalents  0.0969
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.983
_diffrn_reflns_theta_max         27.270
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8760
_reflns_number_gt                5118
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0647P)²+47.4872P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8760
_refine_ls_number_parameters     539
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.1452
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.2069
_refine_ls_wR_factor_gt          0.1804
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.032
_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
F1 F 0.28285(7) 0.3157(3) 0.28247(8) 0.0306(6) Uani 1 1 d . . . . .
F2 F 0.29817(7) 0.0644(3) 0.30297(8) 0.0329(6) Uani 1 1 d . . . . .
F3 F 0.12439(9) 0.1089(3) 0.04003(9) 0.0418(7) Uani 1 1 d . . . . .
F4 F 0.13292(10) 0.0618(4) -0.04567(11) 0.0676(10) Uani 1 1 d . . . . .
F5 F 0.10874(12) 0.2819(5) -0.11585(11) 0.0846(13) Uani 1 1 d . . . . .
F6 F 0.07849(14) 0.5530(5) -0.09719(11) 0.0883(13) Uani 1 1 d . . . . .
F7 F 0.07048(11) 0.6037(3) -0.01242(9) 0.0595(9) Uani 1 1 d . . . . .
F8 F 0.01406(7) 0.2446(3) -0.00894(8) 0.0377(6) Uani 1 1 d . . . . .
F9 F -0.04728(8) 0.0774(3) 0.00494(11) 0.0529(8) Uani 1 1 d . . . . .
F10 F -0.04472(10) 0.0230(3) 0.09730(14) 0.0647(9) Uani 1 1 d . . . . .
F11 F 0.02101(10) 0.1453(3) 0.17539(11) 0.0531(8) Uani 1 1 d . . . . .
F12 F 0.08311(8) 0.3161(3) 0.16245(8) 0.0344(6) Uani 1 1 d . . . . .
F13 F 0.16174(7) 0.5930(3) 0.07615(8) 0.0328(6) Uani 1 1 d . . . . .
F14 F 0.17412(8) 0.8770(3) 0.11203(9) 0.0369(6) Uani 1 1 d . . . . .
F15 F 0.11591(9) 1.0003(3) 0.14780(9) 0.0403(6) Uani 1 1 d . . . . .
F16 F 0.04261(9) 0.8403(3) 0.14155(10) 0.0410(7) Uani 1 1 d . . . . .
F17 F 0.02748(7) 0.5654(2) 0.10228(9) 0.0296(5) Uani 1 1 d . . . . .
N1 N 0.22222(10) 0.1429(4) 0.26345(11) 0.0225(7) Uani 1 1 d . . . . .
N2 N 0.19017(10) 0.1860(4) 0.22336(11) 0.0232(7) Uani 1 1 d . . . . .
N3 N 0.23878(10) 0.1767(4) 0.17857(11) 0.0213(7) Uani 1 1 d . . . . .
N4 N 0.27155(10) 0.1342(3) 0.21770(11) 0.0207(7) Uani 1 1 d . . . . .
N5 N 0.13684(10) 0.3170(4) 0.11122(12) 0.0254(7) Uani 1 1 d . . . . .
C1 C 0.20832(14) 0.0759(5) 0.29971(16) 0.0352(10) Uani 1 1 d . . . . .
C2 C 0.23584(16) 0.0900(6) 0.34872(16) 0.0459(13) Uani 1 1 d . . . . .
H2 H 0.2634 0.1408 0.3578 0.055 Uiso 1 1 calc R U . . .
C3 C 0.2223(2) 0.0286(10) 0.3838(2) 0.084(2) Uani 1 1 d . . . . .
H3 H 0.2404 0.0391 0.4175 0.101 Uiso 1 1 calc R U . . .
C4 C 0.1830(2) -0.0475(10) 0.3705(2) 0.096(3) Uani 1 1 d . . . . .
H4 H 0.1744 -0.0922 0.3949 0.116 Uiso 1 1 calc R U . . .
C5 C 0.1557(2) -0.0594(9) 0.3213(2) 0.079(2) Uani 1 1 d . . . . .
H5 H 0.1282 -0.1106 0.3124 0.095 Uiso 1 1 calc R U . . .
C6 C 0.16813(17) 0.0023(6) 0.28530(19) 0.0488(13) Uani 1 1 d . . . . .
H6 H 0.1496 -0.0056 0.2517 0.059 Uiso 1 1 calc R U . . .
C7 C 0.20202(12) 0.2165(4) 0.18542(14) 0.0219(8) Uani 1 1 d . . . . .
C8 C 0.16692(12) 0.2717(4) 0.14335(14) 0.0221(8) Uani 1 1 d . . . . .
C9 C 0.30723(12) 0.0615(5) 0.20945(14) 0.0262(9) Uani 1 1 d . . . . .
C10 C 0.34984(14) 0.0816(6) 0.24299(17) 0.0401(11) Uani 1 1 d . . . . .
H10 H 0.3554 0.1411 0.2716 0.048 Uiso 1 1 calc R U . . .
C11 C 0.38443(16) 0.0124(7) 0.2338(2) 0.0533(14) Uani 1 1 d . . . . .
H11 H 0.4139 0.0258 0.2562 0.064 Uiso 1 1 calc R U . . .
C12 C 0.37573(18) -0.0753(7) 0.1923(2) 0.0611(16) Uani 1 1 d . . . . .
H12 H 0.3994 -0.1223 0.1863 0.073 Uiso 1 1 calc R U . . .
C13 C 0.33333(18) -0.0953(7) 0.1597(2) 0.0564(15) Uani 1 1 d . . . . .
H13 H 0.3277 -0.1566 0.1314 0.068 Uiso 1 1 calc R U . . .
C14 C 0.29856(15) -0.0263(6) 0.16791(17) 0.0421(12) Uani 1 1 d . . . . .
H14 H 0.2692 -0.0393 0.1453 0.051 Uiso 1 1 calc R U . . .
C15 C 0.09775(12) 0.3606(5) 0.01834(14) 0.0255(9) Uani 1 1 d . . . . .
C16 C 0.11317(13) 0.2226(5) 0.00698(15) 0.0314(10) Uani 1 1 d . . . . .
C17 C 0.11733(15) 0.1959(6) -0.03682(17) 0.0442(13) Uani 1 1 d . . . . .
C18 C 0.10481(17) 0.3046(7) -0.07225(17) 0.0554(15) Uani 1 1 d . . . . .
C19 C 0.09007(18) 0.4426(6) -0.06260(16) 0.0512(14) Uani 1 1 d . . . . .
C20 C 0.08613(15) 0.4671(5) -0.01838(15) 0.0383(11) Uani 1 1 d . . . . .
C21 C 0.05292(12) 0.2846(4) 0.07643(15) 0.0261(9) Uani 1 1 d . . . . .
C22 C 0.01801(13) 0.2219(5) 0.03770(15) 0.0302(10) Uani 1 1 d . . . . .
C23 C -0.01458(14) 0.1336(5) 0.04431(19) 0.0392(12) Uani 1 1 d . . . . .
C24 C -0.01376(15) 0.1091(5) 0.0905(2) 0.0412(12) Uani 1 1 d . . . . .
C25 C 0.01951(16) 0.1699(5) 0.12975(18) 0.0364(11) Uani 1 1 d . . . . .
C26 C 0.05178(13) 0.2567(4) 0.12206(15) 0.0273(9) Uani 1 1 d . . . . .
C27 C 0.09462(12) 0.5633(4) 0.08786(13) 0.0215(8) Uani 1 1 d . . . . .
C28 C 0.13080(12) 0.6525(5) 0.09134(14) 0.0253(9) Uani 1 1 d . . . . .
C29 C 0.13834(12) 0.7978(4) 0.11002(14) 0.0256(9) Uani 1 1 d . . . . .
C30 C 0.10851(14) 0.8612(4) 0.12730(14) 0.0278(9) Uani 1 1 d . . . . .
C31 C 0.07178(14) 0.7799(4) 0.12441(14) 0.0267(9) Uani 1 1 d . . . . .
C32 C 0.06524(12) 0.6354(4) 0.10443(14) 0.0226(8) Uani 1 1 d . . . . .
C33 C 0.0000 0.4032(10) 0.2500 0.0521(18) Uani 1 2 d S TU P . .
H33 H 0.0000 0.2948 0.2500 0.063 Uiso 1 2 calc R U P . .
C34 C 0.00655(16) 0.4826(7) 0.2921(2) 0.0520(13) Uani 1 1 d . U . . .
H34 H 0.0110 0.4285 0.3215 0.062 Uiso 1 1 calc R U . . .
C35 C 0.00675(18) 0.6410(7) 0.2925(2) 0.0546(13) Uani 1 1 d . U . . .
H35 H 0.0116 0.6939 0.3222 0.066 Uiso 1 1 calc R U . . .
C36 C 0.0000 0.7231(10) 0.2500 0.0619(19) Uani 1 2 d S TU P . .
C37 C 0.0000 0.8957(11) 0.2500 0.104(4) Uani 1 2 d S TU P . .
H37A H 0.0285 0.9330 0.2509 0.157 Uiso 0.5 1 calc R U P A -1
H37B H -0.0050 0.9330 0.2788 0.157 Uiso 0.5 1 calc R U P A -1
H37C H -0.0235 0.9330 0.2203 0.157 Uiso 0.5 1 calc R U P A -1
B1 B 0.27132(14) 0.1657(5) 0.26947(15) 0.0240(10) Uani 1 1 d . . . . .
B2 B 0.09230(14) 0.3858(5) 0.07057(16) 0.0236(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
F1 B1 1.381(5) . ?
F2 B1 1.373(5) . ?
F3 C16 1.344(5) . ?
F4 C17 1.345(5) . ?
F5 C18 1.353(5) . ?
F6 C19 1.352(6) . ?
F7 C20 1.339(5) . ?
F8 C22 1.346(5) . ?
F9 C23 1.342(5) . ?
F10 C24 1.338(5) . ?
F11 C25 1.345(5) . ?
F12 C26 1.351(4) . ?
F13 C28 1.356(4) . ?
F14 C29 1.343(4) . ?
F15 C30 1.342(5) . ?
F16 C31 1.345(5) . ?
F17 C32 1.360(4) . ?
N1 N2 1.307(4) . ?
N1 C1 1.435(5) . ?
N1 B1 1.562(5) . ?
N2 C7 1.340(5) . ?
N3 N4 1.300(4) . ?
N3 C7 1.339(5) . ?
N4 C9 1.428(5) . ?
N4 B1 1.553(5) . ?
N5 C8 1.151(5) . ?
N5 B2 1.617(5) . ?
C1 C6 1.381(6) . ?
C1 C2 1.391(6) . ?
C2 C3 1.378(7) . ?
C3 C4 1.369(9) . ?
C4 C5 1.393(9) . ?
C5 C6 1.382(7) . ?
C7 C8 1.422(5) . ?
C9 C14 1.382(6) . ?
C9 C10 1.385(6) . ?
C10 C11 1.396(7) . ?
C11 C12 1.381(8) . ?
C12 C13 1.371(8) . ?
C13 C14 1.388(6) . ?
C15 C20 1.370(6) . ?
C15 C16 1.398(6) . ?
C15 B2 1.630(6) . ?
C16 C17 1.368(6) . ?
C17 C18 1.358(8) . ?
C18 C19 1.371(7) . ?
C19 C20 1.373(6) . ?
C21 C26 1.381(6) . ?
C21 C22 1.390(5) . ?
C21 B2 1.626(6) . ?
C22 C23 1.389(6) . ?
C23 C24 1.367(7) . ?
C24 C25 1.365(7) . ?
C25 C26 1.387(6) . ?
C27 C32 1.383(5) . ?
C27 C28 1.390(6) . ?
C27 B2 1.630(6) . ?
C28 C29 1.372(6) . ?
C29 C30 1.376(6) . ?
C30 C31 1.372(6) . ?
C31 C32 1.379(5) . ?
C33 C34 1.367(7) . ?
C33 C34 1.367(7) 2 ?
C34 C35 1.388(8) . ?
C35 C36 1.389(7) . ?
C36 C35 1.389(7) 2 ?
C36 C37 1.512(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 114.9(3) . . ?
N2 N1 B1 120.6(3) . . ?
C1 N1 B1 124.6(3) . . ?
N1 N2 C7 115.2(3) . . ?
N4 N3 C7 115.5(3) . . ?
N3 N4 C9 115.6(3) . . ?
N3 N4 B1 120.9(3) . . ?
C9 N4 B1 123.5(3) . . ?
C8 N5 B2 173.6(4) . . ?
C6 C1 C2 122.1(4) . . ?
C6 C1 N1 119.6(4) . . ?
C2 C1 N1 118.3(4) . . ?
C3 C2 C1 118.7(5) . . ?
C4 C3 C2 120.4(6) . . ?
C3 C4 C5 120.2(5) . . ?
C6 C5 C4 120.7(6) . . ?
C1 C6 C5 117.9(5) . . ?
N3 C7 N2 129.1(3) . . ?
N3 C7 C8 115.8(3) . . ?
N2 C7 C8 113.8(3) . . ?
N5 C8 C7 175.4(4) . . ?
C14 C9 C10 121.3(4) . . ?
C14 C9 N4 119.3(4) . . ?
C10 C9 N4 119.4(4) . . ?
C9 C10 C11 118.7(5) . . ?
C12 C11 C10 120.0(5) . . ?
C13 C12 C11 120.7(5) . . ?
C12 C13 C14 120.2(5) . . ?
C9 C14 C13 119.2(4) . . ?
C20 C15 C16 114.7(4) . . ?
C20 C15 B2 123.9(4) . . ?
C16 C15 B2 121.4(4) . . ?
F3 C16 C17 117.4(4) . . ?
F3 C16 C15 119.5(4) . . ?
C17 C16 C15 123.1(4) . . ?
F4 C17 C18 119.4(4) . . ?
F4 C17 C16 120.8(5) . . ?
C18 C17 C16 119.8(4) . . ?
F5 C18 C17 121.2(5) . . ?
F5 C18 C19 119.5(5) . . ?
C17 C18 C19 119.2(4) . . ?
F6 C19 C18 119.7(4) . . ?
F6 C19 C20 120.3(5) . . ?
C18 C19 C20 120.0(5) . . ?
F7 C20 C15 120.8(4) . . ?
F7 C20 C19 116.1(4) . . ?
C15 C20 C19 123.1(4) . . ?
C26 C21 C22 114.5(4) . . ?
C26 C21 B2 120.8(3) . . ?
C22 C21 B2 124.7(4) . . ?
F8 C22 C23 116.2(4) . . ?
F8 C22 C21 121.0(4) . . ?
C23 C22 C21 122.9(4) . . ?
F9 C23 C24 120.9(4) . . ?
F9 C23 C22 119.2(5) . . ?
C24 C23 C22 119.8(4) . . ?
F10 C24 C25 120.1(5) . . ?
F10 C24 C23 120.3(5) . . ?
C25 C24 C23 119.6(4) . . ?
F11 C25 C24 120.2(4) . . ?
F11 C25 C26 120.5(4) . . ?
C24 C25 C26 119.3(4) . . ?
F12 C26 C21 120.1(4) . . ?
F12 C26 C25 116.1(4) . . ?
C21 C26 C25 123.8(4) . . ?
C32 C27 C28 113.8(4) . . ?
C32 C27 B2 126.1(4) . . ?
C28 C27 B2 119.9(3) . . ?
F13 C28 C29 116.5(4) . . ?
F13 C28 C27 118.7(3) . . ?
C29 C28 C27 124.8(4) . . ?
F14 C29 C28 121.3(4) . . ?
F14 C29 C30 120.2(4) . . ?
C28 C29 C30 118.5(4) . . ?
F15 C30 C31 120.4(4) . . ?
F15 C30 C29 120.0(4) . . ?
C31 C30 C29 119.6(4) . . ?
F16 C31 C30 120.1(4) . . ?
F16 C31 C32 120.2(4) . . ?
C30 C31 C32 119.7(4) . . ?
F17 C32 C31 115.3(3) . . ?
F17 C32 C27 121.2(3) . . ?
C31 C32 C27 123.6(4) . . ?
C34 C33 C34 118.9(8) . 2 ?
C33 C34 C35 121.0(6) . . ?
C34 C35 C36 120.8(6) . . ?
C35 C36 C35 117.6(8) 2 . ?
C35 C36 C37 121.2(4) 2 . ?
C35 C36 C37 121.2(4) . . ?
F2 B1 F1 112.4(3) . . ?
F2 B1 N4 110.7(3) . . ?
F1 B1 N4 109.9(3) . . ?
F2 B1 N1 110.7(3) . . ?
F1 B1 N1 108.4(3) . . ?
N4 B1 N1 104.4(3) . . ?
N5 B2 C21 104.4(3) . . ?
N5 B2 C15 105.2(3) . . ?
C21 B2 C15 113.5(3) . . ?
N5 B2 C27 101.6(3) . . ?
C21 B2 C27 115.7(3) . . ?
C15 B2 C27 114.6(3) . . ?

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.077



