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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1050730'
_audit_update_record             
;
2015-05-19 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_GOODF01_shelx               
;
PROBLEM: The least squares goodness of fit parameter lies
RESPONSE: Due to the squeeze of both solvent (disordered toluene) and the 
counterion (disordered BF4) unrealistic Goof parameters are obtained
;

# end Validation Reply Form 
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H21 B0 Cl Co F0 N4 O2'
_chemical_formula_weight         527.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           57
_space_group_name_H-M_alt        'P b c m'
_space_group_name_Hall           '-P 2c 2b'

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

_cell_length_a                   8.6043(10)
_cell_length_b                   16.622(2)
_cell_length_c                   21.331(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3050.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            black-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_F_000             1084
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.676
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6349
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS, 2008, Sheldrick'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Apex-II'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12839
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.909
_diffrn_reflns_theta_max         26.967
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3322
_reflns_number_gt                2594
_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       'APEX2  (Bruker AXS, 1)'
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, )'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, )'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ' ORTEP for Windows (Farugia, 1997)'
_computing_publication_material  ?

_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1475P)²+20.8833P] 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         3322
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1485
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   0.560
_refine_ls_restrained_S_all      0.560
_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
C1 C 0.8839(5) 0.9416(2) 0.2500 0.0325(11) Uani 1 2 d S T P . .
C2 C 0.7094(5) 0.9277(2) 0.2500 0.0308(10) Uani 1 2 d S T P . .
C3 C 0.6360(3) 0.96398(17) 0.19071(16) 0.0270(7) Uani 1 1 d . . . . .
C4 C 0.5693(3) 1.07737(18) 0.13499(15) 0.0272(6) Uani 1 1 d . . . . .
H4 H 0.5706 1.1343 0.1308 0.033 Uiso 1 1 calc R U . . .
C5 C 0.4938(4) 1.0332(2) 0.09040(18) 0.0394(8) Uani 1 1 d . . . . .
H5 H 0.4431 1.0588 0.0562 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4929(5) 0.9499(2) 0.09622(19) 0.0466(9) Uani 1 1 d . . . . .
H6 H 0.4436 0.9175 0.0654 0.056 Uiso 1 1 calc R U . . .
C7 C 0.5637(4) 0.91517(19) 0.14678(18) 0.0384(8) Uani 1 1 d . . . . .
H7 H 0.5633 0.8584 0.1518 0.046 Uiso 1 1 calc R U . . .
C8 C 0.9864(6) 0.8771(3) 0.2500 0.060(2) Uani 1 2 d S T P . .
H8 H 0.9489 0.8233 0.2500 0.073 Uiso 1 2 calc R U P . .
C9 C 1.1452(6) 0.8928(3) 0.2500 0.076(3) Uani 1 2 d S T P . .
H9 H 1.2175 0.8496 0.2500 0.091 Uiso 1 2 calc R U P . .
C10 C 1.1973(5) 0.9713(3) 0.2500 0.0559(18) Uani 1 2 d S T P . .
H10 H 1.3053 0.9831 0.2500 0.067 Uiso 1 2 calc R U P . .
C11 C 1.0873(5) 1.0327(3) 0.2500 0.0353(11) Uani 1 2 d S T P . .
C12 C 1.1409(5) 1.1211(2) 0.2500 0.0270(9) Uani 1 2 d S T P . .
C13 C 1.0817(3) 1.16407(16) 0.30898(15) 0.0251(6) Uani 1 1 d . . . . .
C14 C 1.1843(4) 1.1950(2) 0.35248(16) 0.0315(7) Uani 1 1 d . . . . .
H14 H 1.2930 1.1872 0.3473 0.038 Uiso 1 1 calc R U . . .
C15 C 1.1287(4) 1.2372(2) 0.40356(17) 0.0393(8) Uani 1 1 d . . . . .
H15 H 1.1981 1.2584 0.4340 0.047 Uiso 1 1 calc R U . . .
C16 C 0.9701(4) 1.2480(2) 0.40946(16) 0.0358(8) Uani 1 1 d . . . . .
H16 H 0.9282 1.2774 0.4437 0.043 Uiso 1 1 calc R U . . .
C17 C 0.8738(3) 1.21489(18) 0.36434(14) 0.0265(6) Uani 1 1 d . . . . .
H17 H 0.7649 1.2224 0.3685 0.032 Uiso 1 1 calc R U . . .
N1 N 0.9338(4) 1.0188(2) 0.2500 0.0255(8) Uani 1 2 d S T P . .
N2 N 0.6419(3) 1.04431(14) 0.18451(13) 0.0245(5) Uani 1 1 d . . . . .
N3 N 0.9259(3) 1.17293(14) 0.31521(12) 0.0231(5) Uani 1 1 d . . . . .
O1 O 0.6930(4) 0.84299(17) 0.2500 0.0377(8) Uani 1 2 d S T P . .
H1 H 0.6045 0.8307 0.2364 0.057 Uiso 0.5 1 calc R U P . .
O2 O 1.3022(3) 1.11627(17) 0.2500 0.0334(8) Uani 1 2 d S T P . .
H2 H 1.3399 1.1618 0.2422 0.050 Uiso 0.5 1 calc R U P . .
Cl1 Cl 0.58863(9) 1.22709(5) 0.2500 0.0175(2) Uani 1 2 d S T P . .
Co1 Co 0.77247(6) 1.11530(3) 0.2500 0.02005(17) 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
C1 N1 1.354(5) . ?
C1 C8 1.389(6) . ?
C1 C2 1.519(6) . ?
C2 O1 1.416(5) . ?
C2 C3 1.537(4) 8_556 ?
C2 C3 1.537(4) . ?
C3 N2 1.343(4) . ?
C3 C7 1.387(4) . ?
C4 N2 1.345(4) . ?
C4 C5 1.366(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.366(6) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.390(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(6) . ?
C10 H10 0.9500 . ?
C11 N1 1.341(5) . ?
C11 C12 1.541(6) . ?
C12 O2 1.390(5) . ?
C12 C13 1.534(4) 8_556 ?
C12 C13 1.534(4) . ?
C13 N3 1.355(3) . ?
C13 C14 1.380(4) . ?
C14 C15 1.381(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(4) . ?
C16 H16 0.9500 . ?
C17 N3 1.336(4) . ?
C17 H17 0.9500 . ?
N1 Co1 2.121(3) . ?
N2 Co1 2.146(2) . ?
N3 Co1 2.144(2) . ?
O1 H1 0.8400 . ?
O2 H2 0.8400 . ?
Cl1 Co1 2.4403(9) . ?
Co1 N3 2.144(2) 8_556 ?
Co1 N2 2.146(2) 8_556 ?

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 C1 C8 122.0(4) . . ?
N1 C1 C2 117.2(4) . . ?
C8 C1 C2 120.7(4) . . ?
O1 C2 C1 104.5(3) . . ?
O1 C2 C3 110.4(2) . 8_556 ?
C1 C2 C3 110.3(2) . 8_556 ?
O1 C2 C3 110.4(2) . . ?
C1 C2 C3 110.3(2) . . ?
C3 C2 C3 110.8(3) 8_556 . ?
N2 C3 C7 122.1(3) . . ?
N2 C3 C2 117.1(3) . . ?
C7 C3 C2 120.7(3) . . ?
N2 C4 C5 123.3(3) . . ?
N2 C4 H4 118.4 . . ?
C5 C4 H4 118.4 . . ?
C4 C5 C6 118.4(3) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C7 C6 C5 119.3(3) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C3 119.1(3) . . ?
C6 C7 H7 120.5 . . ?
C3 C7 H7 120.5 . . ?
C9 C8 C1 118.7(4) . . ?
C9 C8 H8 120.7 . . ?
C1 C8 H8 120.7 . . ?
C10 C9 C8 119.8(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 118.2(4) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
N1 C11 C10 123.0(4) . . ?
N1 C11 C12 117.3(4) . . ?
C10 C11 C12 119.7(4) . . ?
O2 C12 C13 111.0(2) . 8_556 ?
O2 C12 C13 111.0(2) . . ?
C13 C12 C13 110.2(3) 8_556 . ?
O2 C12 C11 104.1(3) . . ?
C13 C12 C11 110.1(2) 8_556 . ?
C13 C12 C11 110.1(2) . . ?
N3 C13 C14 121.8(3) . . ?
N3 C13 C12 117.4(3) . . ?
C14 C13 C12 120.8(3) . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 118.6(3) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C15 C16 C17 118.4(3) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
N3 C17 C16 123.5(3) . . ?
N3 C17 H17 118.2 . . ?
C16 C17 H17 118.2 . . ?
C11 N1 C1 118.4(4) . . ?
C11 N1 Co1 121.0(3) . . ?
C1 N1 Co1 120.6(3) . . ?
C3 N2 C4 117.8(3) . . ?
C3 N2 Co1 120.2(2) . . ?
C4 N2 Co1 122.00(19) . . ?
C17 N3 C13 117.7(3) . . ?
C17 N3 Co1 122.38(19) . . ?
C13 N3 Co1 119.8(2) . . ?
C2 O1 H1 109.5 . . ?
C12 O2 H2 109.5 . . ?
N1 Co1 N3 86.26(10) . . ?
N1 Co1 N3 86.26(10) . 8_556 ?
N3 Co1 N3 80.91(13) . 8_556 ?
N1 Co1 N2 85.82(9) . 8_556 ?
N3 Co1 N2 98.39(10) . 8_556 ?
N3 Co1 N2 172.07(9) 8_556 8_556 ?
N1 Co1 N2 85.82(9) . . ?
N3 Co1 N2 172.07(9) . . ?
N3 Co1 N2 98.39(10) 8_556 . ?
N2 Co1 N2 81.21(14) 8_556 . ?
N1 Co1 Cl1 179.52(9) . . ?
N3 Co1 Cl1 93.38(7) . . ?
N3 Co1 Cl1 93.38(7) 8_556 . ?
N2 Co1 Cl1 94.55(7) 8_556 . ?
N2 Co1 Cl1 94.55(7) . . ?

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.069

_shelxl_version_number           2014-3



