# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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(tmp)_100K
_database_code_depnum_ccdc_archive 'CCDC 2065245'
loop_
_audit_author_name
_audit_author_address
'Yukihiro Takahashi'
;Hokkaido University
Japan
;
_audit_update_record             
;
2021-02-26 deposited with the CCDC.	2021-04-23 downloaded from the CCDC.
;
_audit_creation_date             2014-12-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 Co N4'
_chemical_formula_sum            'C24 H20 Co N4'
_chemical_formula_weight         423.37
_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'
N N 0.0061 0.0033 '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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.385(4)
_cell_length_b                   5.4371(18)
_cell_length_c                   14.320(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.333(5)
_cell_angle_gamma                90
_cell_volume                     854.9(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3512
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.491
_cell_measurement_theta_min      2.950
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.870
_exptl_absorpt_coefficient_mu    1.024
_exptl_absorpt_correction_T_max  0.965118
_exptl_absorpt_correction_T_min  0.786281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0924 before and 0.0754 after correction.
 The Ratio of minimum to maximum transmission is 0.81.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 13230 reflections, Rint = 0.0672
 (6187 with I > 3sig(I), Rint = 0.0527)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            13230
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         1.855
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEXII Ultra'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1519
_reflns_number_total             1954
_reflns_special_details          
;
 _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       'Bruker SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2 2014.1-1 (Bruker, 2014)'
_computing_data_reduction        'Bruker SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         1.528
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1954
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0593
_refine_ls_restrained_S_all      1.091
_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)+(0.0378P)²+4.8454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1394
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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 0.5000 0.0000 0.5000 0.0092(2) Uani 1 2 d S T P . .
N1 N 0.3208(3) 0.0063(6) 0.45412(19) 0.0095(6) Uani 1 1 d . . . . .
N2 N 0.5089(3) 0.2881(6) 0.4195(2) 0.0093(6) Uani 1 1 d . . . . .
C1 C 0.2386(3) -0.1440(7) 0.4835(3) 0.0121(8) Uani 1 1 d . . . . .
C2 C 0.1161(4) -0.0798(8) 0.4329(3) 0.0171(9) Uani 1 1 d . . . . .
H2 H 0.0439 -0.1533 0.4413 0.021 Uiso 1 1 calc R . . . .
C3 C 0.1225(4) 0.1046(8) 0.3712(3) 0.0163(8) Uani 1 1 d . . . . .
H3 H 0.0556 0.1821 0.3270 0.020 Uiso 1 1 calc R . . . .
C4 C 0.2492(3) 0.1617(8) 0.3849(3) 0.0132(8) Uani 1 1 d . . . . .
C5 C 0.2911(4) 0.3566(8) 0.3401(3) 0.0145(8) Uani 1 1 d . . . . .
C6 C 0.4132(4) 0.4209(7) 0.3618(2) 0.0122(8) Uani 1 1 d . . . . .
C7 C 0.4573(4) 0.6342(8) 0.3233(3) 0.0150(8) Uani 1 1 d . . . . .
H7 H 0.4091 0.7564 0.2834 0.018 Uiso 1 1 calc R . . . .
C8 C 0.5794(4) 0.6295(7) 0.3541(3) 0.0147(8) Uani 1 1 d . . . . .
H8 H 0.6339 0.7476 0.3403 0.018 Uiso 1 1 calc R . . . .
C9 C 0.6118(4) 0.4111(8) 0.4122(3) 0.0123(8) Uani 1 1 d . . . . .
C10 C 0.7311(4) 0.3389(8) 0.4513(3) 0.0142(8) Uani 1 1 d . . . . .
C11 C 0.2020(4) 0.5083(9) 0.2659(3) 0.0202(8) Uani 1 1 d . . . . .
H11A H 0.2336 0.5335 0.2093 0.030 Uiso 1 1 calc GR . . . .
H11B H 0.1906 0.6680 0.2940 0.030 Uiso 1 1 calc GR . . . .
H11C H 0.1237 0.4220 0.2462 0.030 Uiso 1 1 calc GR . . . .
C12 C 0.8313(4) 0.4827(9) 0.4241(3) 0.0194(9) Uani 1 1 d . . . . .
H12A H 0.9062 0.3848 0.4391 0.029 Uiso 1 1 calc GR . . . .
H12B H 0.8457 0.6368 0.4609 0.029 Uiso 1 1 calc GR . . . .
H12C H 0.8066 0.5196 0.3546 0.029 Uiso 1 1 calc GR . . . .


_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 N1 1.971(3) 3_656 ?
Co1 N1 1.971(3) . ?
Co1 N2 1.963(3) . ?
Co1 N2 1.963(3) 3_656 ?
N1 C1 1.389(5) . ?
N1 C4 1.391(5) . ?
N2 C6 1.383(5) . ?
N2 C9 1.377(5) . ?
C1 C2 1.434(6) . ?
C1 C10 1.393(6) 3_656 ?
C2 H2 0.9500 . ?
C2 C3 1.351(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.438(5) . ?
C4 C5 1.387(6) . ?
C5 C6 1.387(6) . ?
C5 C11 1.506(5) . ?
C6 C7 1.431(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.343(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.440(6) . ?
C9 C10 1.382(6) . ?
C10 C1 1.394(6) 3_656 ?
C10 C12 1.517(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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 Co1 N1 180.0 . 3_656 ?
N2 Co1 N1 90.00(13) . 3_656 ?
N2 Co1 N1 90.00(13) 3_656 . ?
N2 Co1 N1 90.00(13) . . ?
N2 Co1 N1 90.00(13) 3_656 3_656 ?
N2 Co1 N2 180.00(13) 3_656 . ?
C1 N1 Co1 127.6(3) . . ?
C1 N1 C4 105.0(3) . . ?
C4 N1 Co1 127.4(3) . . ?
C6 N2 Co1 127.7(3) . . ?
C9 N2 Co1 127.5(3) . . ?
C9 N2 C6 104.6(3) . . ?
N1 C1 C2 110.3(3) . . ?
N1 C1 C10 125.6(3) . 3_656 ?
C10 C1 C2 124.0(4) 3_656 . ?
C1 C2 H2 126.3 . . ?
C3 C2 C1 107.3(4) . . ?
C3 C2 H2 126.3 . . ?
C2 C3 H3 126.4 . . ?
C2 C3 C4 107.3(4) . . ?
C4 C3 H3 126.4 . . ?
N1 C4 C3 110.1(3) . . ?
C5 C4 N1 125.9(4) . . ?
C5 C4 C3 123.9(4) . . ?
C4 C5 C6 122.4(4) . . ?
C4 C5 C11 119.7(4) . . ?
C6 C5 C11 118.0(4) . . ?
N2 C6 C5 125.9(4) . . ?
N2 C6 C7 110.6(3) . . ?
C5 C6 C7 123.4(4) . . ?
C6 C7 H7 126.4 . . ?
C8 C7 C6 107.2(4) . . ?
C8 C7 H7 126.4 . . ?
C7 C8 H8 126.6 . . ?
C7 C8 C9 106.9(4) . . ?
C9 C8 H8 126.6 . . ?
N2 C9 C8 110.5(3) . . ?
N2 C9 C10 126.6(4) . . ?
C10 C9 C8 122.9(4) . . ?
C1 C10 C12 119.6(4) 3_656 . ?
C9 C10 C1 122.0(4) . 3_656 ?
C9 C10 C12 118.3(4) . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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 N1 C1 C2 179.8(2) . . . . ?
Co1 N1 C1 C10 -3.5(6) . . . 3_656 ?
Co1 N1 C4 C3 179.2(3) . . . . ?
Co1 N1 C4 C5 -5.4(6) . . . . ?
Co1 N2 C6 C5 -8.7(5) . . . . ?
Co1 N2 C6 C7 173.5(2) . . . . ?
Co1 N2 C9 C8 -173.4(2) . . . . ?
Co1 N2 C9 C10 8.3(5) . . . . ?
N1 C1 C2 C3 1.4(5) . . . . ?
N1 C4 C5 C6 -1.1(6) . . . . ?
N1 C4 C5 C11 179.8(4) . . . . ?
N2 C6 C7 C8 2.1(4) . . . . ?
N2 C9 C10 C1 -9.7(6) . . . 3_656 ?
N2 C9 C10 C12 172.2(3) . . . . ?
C1 N1 C4 C3 -0.5(4) . . . . ?
C1 N1 C4 C5 174.8(4) . . . . ?
C1 C2 C3 C4 -1.6(4) . . . . ?
C2 C3 C4 N1 1.4(4) . . . . ?
C2 C3 C4 C5 -174.1(4) . . . . ?
C3 C4 C5 C6 173.7(4) . . . . ?
C3 C4 C5 C11 -5.4(6) . . . . ?
C4 N1 C1 C2 -0.5(4) . . . . ?
C4 N1 C1 C10 176.2(4) . . . 3_656 ?
C4 C5 C6 N2 8.4(6) . . . . ?
C4 C5 C6 C7 -174.0(4) . . . . ?
C5 C6 C7 C8 -175.8(3) . . . . ?
C6 N2 C9 C8 3.4(4) . . . . ?
C6 N2 C9 C10 -174.9(4) . . . . ?
C6 C7 C8 C9 0.1(4) . . . . ?
C7 C8 C9 N2 -2.2(4) . . . . ?
C7 C8 C9 C10 176.1(3) . . . . ?
C8 C9 C10 C1 172.3(4) . . . 3_656 ?
C8 C9 C10 C12 -5.9(5) . . . . ?
C9 N2 C6 C5 174.5(4) . . . . ?
C9 N2 C6 C7 -3.3(4) . . . . ?
C10 C1 C2 C3 -175.4(4) 3_656 . . . ?
C11 C5 C6 N2 -172.5(3) . . . . ?
C11 C5 C6 C7 5.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
