# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_compound_2
_database_code_depnum_ccdc_archive 'CCDC 2216062'
loop_
_audit_author_name
_audit_author_address
'Maria Maria Angeles Palacios Lopez'
;Universidad de Granada
Spain
;
_audit_update_record             
;
2022-10-28 deposited with the CCDC.	2022-12-23 downloaded from the CCDC.
;
_audit_creation_date             2022-10-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H27 Co1 N12 P1 S1, 2(B1 F4)'
_chemical_formula_sum            'C18 H27 B2 Co F8 N12 P S'
_chemical_formula_weight         707.09
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/2'
'-y, x-y, z'
'-x, -y, z+1/2'
'-x+y, -x, z'
'y, -x+y, z+1/2'

_cell_length_a                   9.9868(4)
_cell_length_b                   9.9868(4)
_cell_length_c                   16.0438(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1385.77(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.791
_cell_measurement_theta_min      2.355
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8638
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0677 before and 0.0481 after correction.
The Ratio of minimum to maximum transmission is 0.8638.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale red'
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             718
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.081
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12986
_diffrn_reflns_point_group_measured_fraction_full 0.902
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.820
_diffrn_reflns_theta_min         2.355
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.796
_reflns_Friedel_fraction_max     0.755
_reflns_number_gt                2096
_reflns_number_total             2143
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 831 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(7)
_refine_ls_extinction_coef       0.018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2143
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0229
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²+0.6754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0577
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F4) = Uanis(F4A)
3. Others
 Fixed Sof: F4(0.21667) F4A(0.35) F3A(0.11667) F3(0.65)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C2(H2)
4.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.666667 0.333333 0.49091(3) 0.00944(13) Uani 1 3 d S T P . .
N1 N 0.6632(2) 0.1760(2) 0.31553(15) 0.0148(4) Uani 1 1 d . . . . .
P1 P 0.666667 0.333333 0.27477(7) 0.00998(19) Uani 1 3 d S T P . .
C3 C 0.6994(2) 0.0647(2) 0.52270(16) 0.0120(4) Uani 1 1 d . . . . .
N2 N 0.6792(2) 0.1719(2) 0.40039(12) 0.0116(4) Uani 1 1 d . . . . .
N3 N 0.6996(2) 0.1795(2) 0.56544(14) 0.0130(4) Uani 1 1 d . . . . .
F2 F 1.000000 0.000000 0.2368(2) 0.0265(5) Uani 1 3 d S T P . .
B1 B 1.000000 0.000000 0.3249(4) 0.0184(8) Uani 1 3 d S T P . .
N4 N 0.7178(2) -0.0323(2) 0.57431(14) 0.0144(4) Uani 1 1 d . . . . .
F1 F 1.0047(2) 0.13452(18) 0.35116(14) 0.0345(4) Uani 1 1 d . . . . .
C4 C 0.7175(2) 0.1535(3) 0.64772(16) 0.0155(4) Uani 1 1 d . . . . .
H4 H 0.721627 0.216355 0.693188 0.019 Uiso 1 1 calc R U . . .
C5 C 0.7284(3) 0.0229(3) 0.65375(16) 0.0170(4) Uani 1 1 d . . . . .
H5 H 0.740957 -0.021264 0.703488 0.020 Uiso 1 1 calc R U . . .
S1 S 0.666667 0.333333 0.15575(6) 0.0142(2) Uani 1 3 d S T P . .
C1 C 0.6309(3) 0.0399(2) 0.26651(16) 0.0162(4) Uani 1 1 d . . . . .
H1A H 0.539002 -0.050872 0.288816 0.024 Uiso 1 1 calc R U . . .
H1B H 0.719578 0.023314 0.269497 0.024 Uiso 1 1 calc R U . . .
H1C H 0.612497 0.055915 0.208323 0.024 Uiso 1 1 calc R U . . .
C2 C 0.6842(3) 0.0560(3) 0.43330(15) 0.0132(4) Uani 1 1 d . . . . .
H2 H 0.678402 -0.026900 0.401444 0.016 Uiso 1 1 calc R U . . .
C6 C 0.7240(3) -0.1705(3) 0.55053(17) 0.0244(6) Uani 1 1 d . . . . .
H6A H 0.618639 -0.258249 0.545210 0.037 Uiso 1 1 calc R U . . .
H6B H 0.779672 -0.193316 0.593374 0.037 Uiso 1 1 calc R U . . .
H6C H 0.777862 -0.152451 0.497079 0.037 Uiso 1 1 calc R U . . .
F4 F 0.333333 -0.333333 0.3084(4) 0.0332(9) Uani 0.65 3 d S T P A 1
B2 B 0.333333 -0.333333 0.3925(3) 0.0175(9) Uani 1 3 d S T P . .
F4A F 0.3042(6) -0.2193(6) 0.3563(4) 0.0332(9) Uani 0.35 1 d . . P A 2
F3A F 0.333333 -0.333333 0.4690(6) 0.050(3) Uani 0.35 3 d S T P A 2
F3 F 0.3316(4) -0.2036(4) 0.4215(2) 0.0480(9) Uani 0.65 1 d . . P A 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
Co1 N2 2.2195(19) . ?
Co1 N2 2.2195(19) 5_665 ?
Co1 N2 2.2195(19) 3_655 ?
Co1 N3 2.098(2) . ?
Co1 N3 2.098(2) 5_665 ?
Co1 N3 2.098(2) 3_655 ?
N1 P1 1.6862(19) . ?
N1 N2 1.374(3) . ?
N1 C1 1.460(3) . ?
P1 S1 1.9095(16) . ?
C3 N3 1.335(3) . ?
C3 N4 1.355(3) . ?
C3 C2 1.440(3) . ?
N2 C2 1.295(3) . ?
N3 C4 1.374(3) . ?
F2 B1 1.413(7) . ?
B1 F1 1.386(3) 3_645 ?
B1 F1 1.386(3) 5_765 ?
B1 F1 1.386(3) . ?
N4 C5 1.372(3) . ?
N4 C6 1.463(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.365(3) . ?
C5 H5 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
F4 B2 1.348(8) . ?
B2 F4A 1.431(6) 3_545 ?
B2 F4A 1.431(6) . ?
B2 F4A 1.431(6) 5_655 ?
B2 F3A 1.228(11) . ?
B2 F3 1.385(3) 5_655 ?
B2 F3 1.385(3) . ?
B2 F3 1.385(3) 3_545 ?

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 Co1 N2 81.83(8) . 5_665 ?
N2 Co1 N2 81.83(8) 3_655 5_665 ?
N2 Co1 N2 81.83(8) . 3_655 ?
N3 Co1 N2 75.80(7) . . ?
N3 Co1 N2 75.80(7) 3_655 3_655 ?
N3 Co1 N2 137.43(7) . 5_665 ?
N3 Co1 N2 137.43(7) 3_655 . ?
N3 Co1 N2 137.43(7) 5_665 3_655 ?
N3 Co1 N2 128.87(7) 5_665 . ?
N3 Co1 N2 75.80(7) 5_665 5_665 ?
N3 Co1 N2 128.87(7) . 3_655 ?
N3 Co1 N2 128.87(7) 3_655 5_665 ?
N3 Co1 N3 90.73(8) . 3_655 ?
N3 Co1 N3 90.73(8) 3_655 5_665 ?
N3 Co1 N3 90.73(8) . 5_665 ?
N2 N1 P1 117.63(15) . . ?
N2 N1 C1 118.73(18) . . ?
C1 N1 P1 123.41(18) . . ?
N1 P1 N1 105.93(9) 3_655 5_665 ?
N1 P1 N1 105.93(9) . 3_655 ?
N1 P1 N1 105.93(9) . 5_665 ?
N1 P1 S1 112.82(8) . . ?
N1 P1 S1 112.82(8) 5_665 . ?
N1 P1 S1 112.82(8) 3_655 . ?
N3 C3 N4 111.0(2) . . ?
N3 C3 C2 121.2(2) . . ?
N4 C3 C2 127.8(2) . . ?
N1 N2 Co1 125.25(13) . . ?
C2 N2 Co1 115.06(16) . . ?
C2 N2 N1 119.19(19) . . ?
C3 N3 Co1 113.74(16) . . ?
C3 N3 C4 105.96(19) . . ?
C4 N3 Co1 140.25(16) . . ?
F1 B1 F2 107.7(3) . . ?
F1 B1 F2 107.7(3) 3_645 . ?
F1 B1 F2 107.7(3) 5_765 . ?
F1 B1 F1 111.2(3) . 3_645 ?
F1 B1 F1 111.2(3) . 5_765 ?
F1 B1 F1 111.2(3) 3_645 5_765 ?
C3 N4 C5 106.94(18) . . ?
C3 N4 C6 126.9(2) . . ?
C5 N4 C6 126.2(2) . . ?
N3 C4 H4 125.4 . . ?
C5 C4 N3 109.2(2) . . ?
C5 C4 H4 125.4 . . ?
N4 C5 H5 126.5 . . ?
C4 C5 N4 106.9(2) . . ?
C4 C5 H5 126.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2 123.1 . . ?
N2 C2 C3 113.7(2) . . ?
N2 C2 H2 123.1 . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
N4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
F4 B2 F4A 66.1(3) . 3_545 ?
F4 B2 F4A 66.1(3) . 5_655 ?
F4 B2 F3 109.6(3) . . ?
F4 B2 F3 109.6(3) . 3_545 ?
F4 B2 F3 109.6(3) . 5_655 ?
F4A B2 F4A 104.7(4) . 3_545 ?
F3A B2 F4A 113.9(3) . 3_545 ?
F3A B2 F4A 113.9(3) . . ?
F3A B2 F3 70.4(3) . 3_545 ?
F3A B2 F3 70.4(3) . 5_655 ?
F3 B2 F4A 44.7(3) 5_655 5_655 ?
F3 B2 F4A 134.0(3) 3_545 5_655 ?
F3 B2 F4A 115.1(3) . 5_655 ?
F3 B2 F4A 134.0(3) . 3_545 ?
F3 B2 F4A 44.7(3) 3_545 3_545 ?
F3 B2 F4A 115.1(3) 5_655 3_545 ?
F3 B2 F3 109.3(3) 3_545 5_655 ?
F3 B2 F3 109.3(3) . 5_655 ?
F3 B2 F3 109.3(3) . 3_545 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 N2 C2 C3 -7.1(2) . . . . ?
Co1 N3 C4 C5 177.54(17) . . . . ?
N1 N2 C2 C3 -179.35(18) . . . . ?
P1 N1 N2 Co1 11.7(2) . . . . ?
P1 N1 N2 C2 -176.84(16) . . . . ?
C3 N3 C4 C5 0.2(2) . . . . ?
C3 N4 C5 C4 -0.5(2) . . . . ?
N2 N1 P1 N1 49.50(17) . . . 3_655 ?
N2 N1 P1 N1 -62.72(15) . . . 5_665 ?
N2 N1 P1 S1 173.39(13) . . . . ?
N3 C3 N4 C5 0.7(2) . . . . ?
N3 C3 N4 C6 -179.7(2) . . . . ?
N3 C3 C2 N2 3.3(3) . . . . ?
N3 C4 C5 N4 0.2(3) . . . . ?
N4 C3 N3 Co1 -178.69(13) . . . . ?
N4 C3 N3 C4 -0.5(2) . . . . ?
N4 C3 C2 N2 -175.3(2) . . . . ?
C1 N1 P1 N1 111.7(2) . . . 5_665 ?
C1 N1 P1 N1 -136.0(2) . . . 3_655 ?
C1 N1 P1 S1 -12.1(2) . . . . ?
C1 N1 N2 Co1 -163.02(15) . . . . ?
C1 N1 N2 C2 8.4(3) . . . . ?
C2 C3 N3 Co1 2.5(3) . . . . ?
C2 C3 N3 C4 -179.4(2) . . . . ?
C2 C3 N4 C5 179.4(2) . . . . ?
C2 C3 N4 C6 -1.0(4) . . . . ?
C6 N4 C5 C4 179.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_compound_1
_database_code_depnum_ccdc_archive 'CCDC 2216063'
loop_
_audit_author_name
_audit_author_address
'Maria Maria Angeles Palacios Lopez'
;Universidad de Granada
Spain
;
_audit_update_record             
;
2022-10-28 deposited with the CCDC.	2022-12-23 downloaded from the CCDC.
;
_audit_creation_date             2022-04-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H27 Co1 N12 P1 S1, 2(Cl1 O4)'
_chemical_formula_sum            'C18 H27 Cl2 Co N12 O8 P S'
_chemical_formula_weight         732.37
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'
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'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/2'
'-y, x-y, z'
'-x, -y, z+1/2'
'-x+y, -x, z'
'y, -x+y, z+1/2'

_cell_length_a                   10.1198(13)
_cell_length_b                   10.1198(13)
_cell_length_c                   16.131(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1430.7(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9440
_cell_measurement_temperature    99.9
_cell_measurement_theta_max      28.396
_cell_measurement_theta_min      2.324
_shelx_estimated_absorpt_T_max   0.832
_shelx_estimated_absorpt_T_min   0.671
_exptl_absorpt_coefficient_mu    0.982
_exptl_absorpt_correction_T_max  0.7899
_exptl_absorpt_correction_T_min  0.6526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0926 before and 0.0646 after correction.
The Ratio of minimum to maximum transmission is 0.8262.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             750
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.194
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24534
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.397
_diffrn_reflns_theta_min         2.324
_diffrn_ambient_temperature      99.9
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'four circle diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                2256
_reflns_number_total             2376
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 1029 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(13)
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2376
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+0.8899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0828
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O3) = Uanis(O3A)
Uanis(O4) = Uanis(O4A)
3. Others
 Fixed Sof: O3(0.16667) O4A(0.16667) O3A(0.5) O4(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5)
4.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.6667 0.3333 0.30699(4) 0.01284(19) Uani 1 3 d S T P . .
S1 S 0.6667 0.3333 -0.02664(9) 0.0180(3) Uani 1 3 d S T P . .
P1 P 0.6667 0.3333 0.09218(9) 0.0126(3) Uani 1 3 d S T P . .
N1 N 0.6621(3) 0.1773(3) 0.13246(19) 0.0189(5) Uani 1 1 d . . . . .
N4 N 0.7183(3) -0.0269(3) 0.3906(2) 0.0199(5) Uani 1 1 d . . . . .
N3 N 0.7020(3) 0.1833(3) 0.38095(18) 0.0176(5) Uani 1 1 d . . . . .
C3 C 0.7011(3) 0.0690(4) 0.3394(2) 0.0161(6) Uani 1 1 d . . . . .
C1 C 0.6325(4) 0.0442(4) 0.0831(2) 0.0199(6) Uani 1 1 d . . . . .
H1A H 0.6212 0.0633 0.0246 0.030 Uiso 1 1 calc R U . . .
H1B H 0.5385 -0.0451 0.1025 0.030 Uiso 1 1 calc R U . . .
H1C H 0.7180 0.0253 0.0890 0.030 Uiso 1 1 calc R U . . .
N2 N 0.6789(3) 0.1733(3) 0.21686(17) 0.0159(5) Uani 1 1 d . . . . .
C2 C 0.6852(4) 0.0601(4) 0.24989(19) 0.0162(6) Uani 1 1 d . . . . .
H2 H 0.6798 -0.0217 0.2183 0.019 Uiso 1 1 calc R U . . .
C4 C 0.7185(4) 0.1574(4) 0.4630(2) 0.0214(6) Uani 1 1 d . . . . .
H4 H 0.7225 0.2198 0.5081 0.026 Uiso 1 1 calc R U . . .
C5 C 0.7283(4) 0.0282(4) 0.4697(2) 0.0224(7) Uani 1 1 d . . . . .
H5 H 0.7397 -0.0154 0.5194 0.027 Uiso 1 1 calc R U . . .
C6 C 0.7227(5) -0.1648(5) 0.3679(2) 0.0313(9) Uani 1 1 d . . . . .
H6A H 0.6184 -0.2515 0.3645 0.047 Uiso 1 1 calc R U . . .
H6B H 0.7797 -0.1857 0.4100 0.047 Uiso 1 1 calc R U . . .
H6C H 0.7731 -0.1497 0.3140 0.047 Uiso 1 1 calc R U . . .
Cl1 Cl 1.0000 0.0000 0.13945(11) 0.0189(3) Uani 1 3 d S T P . .
O2 O 1.0067(4) 0.1387(3) 0.1677(2) 0.0357(7) Uani 1 1 d . . . . .
O1 O 1.0000 0.0000 0.0503(3) 0.0273(9) Uani 1 3 d S T P . .
Cl2 Cl 0.3333 -0.3333 0.20974(10) 0.0231(3) Uani 1 3 d S T P . .
O3 O 0.3333 -0.3333 0.1262(9) 0.0365(13) Uani 0.5 3 d S T P A 1
O4A O 0.3333 -0.3333 0.2927(11) 0.064(2) Uani 0.5 3 d S T P A 2
O3A O 0.4807(7) -0.3043(7) 0.1749(5) 0.0365(13) Uani 0.5 1 d . . P A 2
O4 O 0.3340(11) -0.1992(11) 0.2429(6) 0.064(2) Uani 0.5 1 d . . P A 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
Co1 N3 2.098(3) . ?
Co1 N3 2.098(3) 3_655 ?
Co1 N3 2.098(3) 5_665 ?
Co1 N2 2.225(3) . ?
Co1 N2 2.225(3) 5_665 ?
Co1 N2 2.225(3) 3_655 ?
S1 P1 1.917(2) . ?
P1 N1 1.686(3) 3_655 ?
P1 N1 1.686(3) . ?
P1 N1 1.686(3) 5_665 ?
N1 C1 1.461(4) . ?
N1 N2 1.375(4) . ?
N4 C3 1.350(4) . ?
N4 C5 1.376(5) . ?
N4 C6 1.466(4) . ?
N3 C3 1.333(4) . ?
N3 C4 1.376(4) . ?
C3 C2 1.450(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 C2 1.293(4) . ?
C2 H2 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.363(5) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
Cl1 O2 1.444(3) 5_765 ?
Cl1 O2 1.444(3) . ?
Cl1 O2 1.444(3) 3_645 ?
Cl1 O1 1.437(5) . ?
Cl2 O3 1.348(14) . ?
Cl2 O4A 1.338(18) . ?
Cl2 O3A 1.479(7) 5_655 ?
Cl2 O3A 1.479(7) 3_545 ?
Cl2 O3A 1.479(7) . ?
Cl2 O4 1.456(10) 5_655 ?
Cl2 O4 1.456(10) . ?
Cl2 O4 1.456(10) 3_545 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Co1 N3 90.86(11) . 3_655 ?
N3 Co1 N3 90.86(11) . 5_665 ?
N3 Co1 N3 90.86(11) 3_655 5_665 ?
N3 Co1 N2 128.16(11) . 3_655 ?
N3 Co1 N2 75.70(10) 5_665 5_665 ?
N3 Co1 N2 138.05(11) . 5_665 ?
N3 Co1 N2 75.70(10) 3_655 3_655 ?
N3 Co1 N2 75.70(10) . . ?
N3 Co1 N2 128.16(11) 3_655 5_665 ?
N3 Co1 N2 138.05(11) 3_655 . ?
N3 Co1 N2 128.16(11) 5_665 . ?
N3 Co1 N2 138.05(11) 5_665 3_655 ?
N2 Co1 N2 81.94(11) . 5_665 ?
N2 Co1 N2 81.94(11) . 3_655 ?
N2 Co1 N2 81.94(11) 3_655 5_665 ?
N1 P1 S1 112.66(11) 3_655 . ?
N1 P1 S1 112.66(11) 5_665 . ?
N1 P1 S1 112.66(11) . . ?
N1 P1 N1 106.10(12) . 3_655 ?
N1 P1 N1 106.10(12) 3_655 5_665 ?
N1 P1 N1 106.10(12) . 5_665 ?
C1 N1 P1 123.4(2) . . ?
N2 N1 P1 117.6(2) . . ?
N2 N1 C1 118.9(3) . . ?
C3 N4 C5 106.6(3) . . ?
C3 N4 C6 127.5(3) . . ?
C5 N4 C6 125.9(3) . . ?
C3 N3 Co1 114.3(2) . . ?
C3 N3 C4 105.5(3) . . ?
C4 N3 Co1 140.0(2) . . ?
N4 C3 C2 127.9(3) . . ?
N3 C3 N4 111.6(3) . . ?
N3 C3 C2 120.5(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 N2 Co1 124.9(2) . . ?
C2 N2 Co1 114.9(2) . . ?
C2 N2 N1 119.7(3) . . ?
C3 C2 H2 123.0 . . ?
N2 C2 C3 114.1(3) . . ?
N2 C2 H2 123.0 . . ?
N3 C4 H4 125.3 . . ?
C5 C4 N3 109.4(3) . . ?
C5 C4 H4 125.3 . . ?
N4 C5 H5 126.6 . . ?
C4 C5 N4 106.9(3) . . ?
C4 C5 H5 126.6 . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
N4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 Cl1 O2 110.54(16) 3_645 5_765 ?
O2 Cl1 O2 110.54(16) 5_765 . ?
O2 Cl1 O2 110.53(16) 3_645 . ?
O1 Cl1 O2 108.39(16) . . ?
O1 Cl1 O2 108.38(16) . 3_645 ?
O1 Cl1 O2 108.38(16) . 5_765 ?
O3 Cl2 O4 111.6(4) . 3_545 ?
O3 Cl2 O4 111.6(4) . . ?
O3 Cl2 O4 111.6(4) . 5_655 ?
O4A Cl2 O3A 112.3(3) . 5_655 ?
O4A Cl2 O3A 112.3(3) . . ?
O4A Cl2 O3A 112.3(3) . 3_545 ?
O3A Cl2 O3A 106.5(3) 5_655 . ?
O3A Cl2 O3A 106.5(3) 3_545 . ?
O3A Cl2 O3A 106.5(3) 3_545 5_655 ?
O4 Cl2 O4 107.3(4) . 5_655 ?
O4 Cl2 O4 107.3(4) 3_545 5_655 ?
O4 Cl2 O4 107.3(4) . 3_545 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 N3 C3 N4 -177.5(2) . . . . ?
Co1 N3 C3 C2 3.3(4) . . . . ?
Co1 N3 C4 C5 175.7(3) . . . . ?
Co1 N2 C2 C3 -6.9(4) . . . . ?
S1 P1 N1 C1 -10.8(3) . . . . ?
S1 P1 N1 N2 172.90(19) . . . . ?
P1 N1 N2 Co1 12.5(3) . . . . ?
P1 N1 N2 C2 -175.9(2) . . . . ?
N1 P1 N1 C1 112.9(3) 5_665 . . . ?
N1 P1 N1 C1 -134.5(3) 3_655 . . . ?
N1 P1 N1 N2 -63.4(2) 5_665 . . . ?
N1 P1 N1 N2 49.2(2) 3_655 . . . ?
N1 N2 C2 C3 -179.3(3) . . . . ?
N4 C3 C2 N2 -176.4(3) . . . . ?
N3 C3 C2 N2 2.7(4) . . . . ?
N3 C4 C5 N4 0.2(4) . . . . ?
C3 N4 C5 C4 -0.7(4) . . . . ?
C3 N3 C4 C5 0.4(4) . . . . ?
C1 N1 N2 Co1 -164.0(2) . . . . ?
C1 N1 N2 C2 7.6(4) . . . . ?
C4 N3 C3 N4 -0.8(4) . . . . ?
C4 N3 C3 C2 179.9(3) . . . . ?
C5 N4 C3 N3 1.0(4) . . . . ?
C5 N4 C3 C2 -179.9(3) . . . . ?
C6 N4 C3 N3 179.9(3) . . . . ?
C6 N4 C3 C2 -0.9(6) . . . . ?
C6 N4 C5 C4 -179.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       'Magnetic properties'
