# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_XW237
_database_code_depnum_ccdc_archive 'CCDC 1991068'
loop_
_audit_author_name
_audit_author_address
'Wang Xiqu'
;university of houston
United States of America
;
_audit_update_record             
;
2020-03-17 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.33

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'
H H 0.0000 0.0000 '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'
O O 0.0492 0.0322 '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                   10.7539(7)
_cell_length_b                   15.7753(11)
_cell_length_c                   10.6322(7)
_cell_angle_alpha                90
_cell_angle_beta                 118.742(2)
_cell_angle_gamma                90
_cell_volume                     1581.48(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      4.69
_cell_measurement_theta_max      67.86

_exptl_crystal_description       PLATE
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.709
_shelx_estimated_absorpt_T_min   0.779
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6406
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III PHOTON'
_diffrn_measurement_method       'narrow frame ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12200
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.690
_diffrn_reflns_theta_max         67.854
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             2801
_reflns_number_gt                2774
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0485P)²+0.5447P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_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         2801
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
O1 O 0.45113(8) 0.13501(5) 0.80602(8) 0.0251(2) Uani 1 1 d . . . . .
O2 O -0.11799(8) 0.07338(5) 0.38064(8) 0.0261(2) Uani 1 1 d . . . . .
O3 O 0.29895(8) 0.06025(5) 0.85076(8) 0.0272(2) Uani 1 1 d . . . . .
N1 N 0.09757(9) 0.10141(6) 0.57010(9) 0.0205(2) Uani 1 1 d . . . . .
H1N H 0.1050(13) 0.0489(10) 0.5933(14) 0.025 Uiso 1 1 d . U . . .
C1 C 0.69970(13) 0.11279(11) 0.91700(15) 0.0428(4) Uani 1 1 d . . . . .
H16 H 0.690314 0.086633 0.829244 0.064 Uiso 1 1 calc R U . . .
H1 H 0.782560 0.089081 1.000403 0.064 Uiso 1 1 calc R U . . .
H3 H 0.711684 0.174165 0.913321 0.064 Uiso 1 1 calc R U . . .
C2 C 0.56985(11) 0.09531(8) 0.92918(12) 0.0281(3) Uani 1 1 d . . . . .
H14 H 0.554286 0.033442 0.928904 0.034 Uiso 1 1 calc R U . . .
H15 H 0.579730 0.119254 1.019603 0.034 Uiso 1 1 calc R U . . .
C3 C 0.32277(11) 0.11214(6) 0.78217(11) 0.0193(2) Uani 1 1 d . . . . .
C4 C 0.20758(10) 0.15581(7) 0.65363(11) 0.0191(2) Uani 1 1 d . . . . .
C5 C 0.20496(10) 0.23932(7) 0.62077(11) 0.0191(2) Uani 1 1 d . . . . .
C6 C 0.08549(10) 0.26967(7) 0.48880(11) 0.0189(2) Uani 1 1 d . . . . .
C7 C 0.07339(11) 0.35434(7) 0.44249(11) 0.0209(2) Uani 1 1 d . . . . .
H4 H 0.142933 0.394375 0.501842 0.025 Uiso 1 1 calc R U . . .
C8 C -0.03735(11) 0.38073(7) 0.31257(12) 0.0234(2) Uani 1 1 d . . . . .
C9 C -0.13792(12) 0.32061(8) 0.22380(12) 0.0269(3) Uani 1 1 d . . . . .
H2 H -0.210811 0.337071 0.131704 0.032 Uiso 1 1 calc R U . . .
C10 C -0.13190(11) 0.23834(7) 0.26882(12) 0.0253(3) Uani 1 1 d . . . . .
H5 H -0.202840 0.199040 0.209303 0.030 Uiso 1 1 calc R U . . .
C11 C -0.02224(11) 0.21204(7) 0.40146(11) 0.0204(2) Uani 1 1 d . . . . .
C12 C -0.02045(11) 0.12460(7) 0.44743(11) 0.0205(2) Uani 1 1 d . . . . .
C13 C -0.05294(12) 0.47244(7) 0.26804(13) 0.0295(3) Uani 1 1 d . . . . .
H7 H -0.101615 0.503362 0.311655 0.044 Uiso 1 1 calc R U . . .
H8 H -0.108462 0.476416 0.163342 0.044 Uiso 1 1 calc R U . . .
H6 H 0.041127 0.497221 0.300161 0.044 Uiso 1 1 calc R U . . .
C14 C 0.31776(11) 0.29864(6) 0.71985(11) 0.0196(2) Uani 1 1 d . . . . .
C15 C 0.32431(12) 0.32038(7) 0.84961(12) 0.0267(3) Uani 1 1 d . . . . .
H9 H 0.255677 0.298551 0.873065 0.032 Uiso 1 1 calc R U . . .
C16 C 0.43058(14) 0.37387(8) 0.94541(13) 0.0334(3) Uani 1 1 d . . . . .
H10 H 0.434877 0.387918 1.034301 0.040 Uiso 1 1 calc R U . . .
C17 C 0.52963(12) 0.40648(7) 0.91141(13) 0.0300(3) Uani 1 1 d . . . . .
H11 H 0.601605 0.443429 0.976486 0.036 Uiso 1 1 calc R U . . .
C18 C 0.52430(12) 0.38539(8) 0.78232(13) 0.0297(3) Uani 1 1 d . . . . .
H13 H 0.593018 0.407459 0.759198 0.036 Uiso 1 1 calc R U . . .
C19 C 0.41817(12) 0.33189(7) 0.68684(12) 0.0269(3) Uani 1 1 d . . . . .
H12 H 0.414267 0.317915 0.598098 0.032 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
O1 C3 1.3278(13) . ?
O1 C2 1.4591(13) . ?
O2 C12 1.2413(13) . ?
O3 C3 1.2031(13) . ?
N1 C12 1.3616(14) . ?
N1 C4 1.3836(13) . ?
N1 H1N 0.857(15) . ?
C1 C2 1.4888(17) . ?
C1 H16 0.9800 . ?
C1 H1 0.9800 . ?
C1 H3 0.9800 . ?
C2 H14 0.9900 . ?
C2 H15 0.9900 . ?
C3 C4 1.4996(14) . ?
C4 C5 1.3597(15) . ?
C5 C6 1.4542(14) . ?
C5 C14 1.4927(14) . ?
C6 C7 1.4078(15) . ?
C6 C11 1.4128(15) . ?
C7 C8 1.3847(15) . ?
C7 H4 0.9500 . ?
C8 C9 1.4064(16) . ?
C8 C13 1.5065(15) . ?
C9 C10 1.3740(17) . ?
C9 H2 0.9500 . ?
C10 C11 1.3973(15) . ?
C10 H5 0.9500 . ?
C11 C12 1.4605(15) . ?
C13 H7 0.9800 . ?
C13 H8 0.9800 . ?
C13 H6 0.9800 . ?
C14 C19 1.3887(16) . ?
C14 C15 1.3902(16) . ?
C15 C16 1.3913(17) . ?
C15 H9 0.9500 . ?
C16 C17 1.3786(19) . ?
C16 H10 0.9500 . ?
C17 C18 1.3863(18) . ?
C17 H11 0.9500 . ?
C18 C19 1.3897(16) . ?
C18 H13 0.9500 . ?
C19 H12 0.9500 . ?

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
C3 O1 C2 115.81(8) . . ?
C12 N1 C4 124.31(9) . . ?
C12 N1 H1N 116.8(9) . . ?
C4 N1 H1N 118.8(9) . . ?
C2 C1 H16 109.5 . . ?
C2 C1 H1 109.5 . . ?
H16 C1 H1 109.5 . . ?
C2 C1 H3 109.5 . . ?
H16 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
O1 C2 C1 107.16(9) . . ?
O1 C2 H14 110.3 . . ?
C1 C2 H14 110.3 . . ?
O1 C2 H15 110.3 . . ?
C1 C2 H15 110.3 . . ?
H14 C2 H15 108.5 . . ?
O3 C3 O1 125.02(10) . . ?
O3 C3 C4 122.80(9) . . ?
O1 C3 C4 112.12(8) . . ?
C5 C4 N1 122.03(9) . . ?
C5 C4 C3 125.82(9) . . ?
N1 C4 C3 112.12(9) . . ?
C4 C5 C6 117.80(9) . . ?
C4 C5 C14 121.11(9) . . ?
C6 C5 C14 121.04(9) . . ?
C7 C6 C11 118.16(9) . . ?
C7 C6 C5 122.68(9) . . ?
C11 C6 C5 119.15(9) . . ?
C8 C7 C6 121.64(10) . . ?
C8 C7 H4 119.2 . . ?
C6 C7 H4 119.2 . . ?
C7 C8 C9 118.80(10) . . ?
C7 C8 C13 120.97(10) . . ?
C9 C8 C13 120.21(10) . . ?
C10 C9 C8 120.72(10) . . ?
C10 C9 H2 119.6 . . ?
C8 C9 H2 119.6 . . ?
C9 C10 C11 120.50(10) . . ?
C9 C10 H5 119.7 . . ?
C11 C10 H5 119.7 . . ?
C10 C11 C6 119.98(10) . . ?
C10 C11 C12 119.15(10) . . ?
C6 C11 C12 120.87(9) . . ?
O2 C12 N1 121.01(10) . . ?
O2 C12 C11 123.49(10) . . ?
N1 C12 C11 115.50(9) . . ?
C8 C13 H7 109.5 . . ?
C8 C13 H8 109.5 . . ?
H7 C13 H8 109.5 . . ?
C8 C13 H6 109.5 . . ?
H7 C13 H6 109.5 . . ?
H8 C13 H6 109.5 . . ?
C19 C14 C15 118.89(10) . . ?
C19 C14 C5 121.68(9) . . ?
C15 C14 C5 119.42(9) . . ?
C14 C15 C16 120.52(11) . . ?
C14 C15 H9 119.7 . . ?
C16 C15 H9 119.7 . . ?
C17 C16 C15 120.04(11) . . ?
C17 C16 H10 120.0 . . ?
C15 C16 H10 120.0 . . ?
C16 C17 C18 120.05(11) . . ?
C16 C17 H11 120.0 . . ?
C18 C17 H11 120.0 . . ?
C17 C18 C19 119.83(11) . . ?
C17 C18 H13 120.1 . . ?
C19 C18 H13 120.1 . . ?
C14 C19 C18 120.66(11) . . ?
C14 C19 H12 119.7 . . ?
C18 C19 H12 119.7 . . ?

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
C3 O1 C2 C1 166.85(11) . . . . ?
C2 O1 C3 O3 -2.53(15) . . . . ?
C2 O1 C3 C4 -179.86(9) . . . . ?
C12 N1 C4 C5 1.58(16) . . . . ?
C12 N1 C4 C3 179.90(9) . . . . ?
O3 C3 C4 C5 138.93(11) . . . . ?
O1 C3 C4 C5 -43.66(14) . . . . ?
O3 C3 C4 N1 -39.31(14) . . . . ?
O1 C3 C4 N1 138.10(9) . . . . ?
N1 C4 C5 C6 -3.58(15) . . . . ?
C3 C4 C5 C6 178.35(9) . . . . ?
N1 C4 C5 C14 173.89(9) . . . . ?
C3 C4 C5 C14 -4.19(16) . . . . ?
C4 C5 C6 C7 -178.52(9) . . . . ?
C14 C5 C6 C7 4.02(15) . . . . ?
C4 C5 C6 C11 0.37(14) . . . . ?
C14 C5 C6 C11 -177.09(9) . . . . ?
C11 C6 C7 C8 -2.51(15) . . . . ?
C5 C6 C7 C8 176.39(9) . . . . ?
C6 C7 C8 C9 -1.53(16) . . . . ?
C6 C7 C8 C13 176.81(10) . . . . ?
C7 C8 C9 C10 4.13(17) . . . . ?
C13 C8 C9 C10 -174.22(11) . . . . ?
C8 C9 C10 C11 -2.59(18) . . . . ?
C9 C10 C11 C6 -1.58(17) . . . . ?
C9 C10 C11 C12 178.79(10) . . . . ?
C7 C6 C11 C10 4.07(15) . . . . ?
C5 C6 C11 C10 -174.87(9) . . . . ?
C7 C6 C11 C12 -176.31(9) . . . . ?
C5 C6 C11 C12 4.75(15) . . . . ?
C4 N1 C12 O2 -177.02(10) . . . . ?
C4 N1 C12 C11 3.50(15) . . . . ?
C10 C11 C12 O2 -6.39(16) . . . . ?
C6 C11 C12 O2 173.98(10) . . . . ?
C10 C11 C12 N1 173.07(9) . . . . ?
C6 C11 C12 N1 -6.56(14) . . . . ?
C4 C5 C14 C19 108.98(12) . . . . ?
C6 C5 C14 C19 -73.64(13) . . . . ?
C4 C5 C14 C15 -70.03(14) . . . . ?
C6 C5 C14 C15 107.36(12) . . . . ?
C19 C14 C15 C16 -0.65(17) . . . . ?
C5 C14 C15 C16 178.38(10) . . . . ?
C14 C15 C16 C17 0.67(18) . . . . ?
C15 C16 C17 C18 -0.61(18) . . . . ?
C16 C17 C18 C19 0.54(18) . . . . ?
C15 C14 C19 C18 0.58(17) . . . . ?
C5 C14 C19 C18 -178.43(10) . . . . ?
C17 C18 C19 C14 -0.53(18) . . . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.033



####################################################################### 
# 
# 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_Kwak1_XW251
_database_code_depnum_ccdc_archive 'CCDC 2014034'
loop_
_audit_author_name
_audit_author_address
'Wang Xiqu'
;university of houston
United States of America
;
_audit_update_record             
;
2020-07-04 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H26 Co I N2 O2'
_chemical_formula_weight         548.29


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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_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                   8.4964(11)
_cell_length_b                   31.850(4)
_cell_length_c                   8.5016(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.618(3)
_cell_angle_gamma                90
_cell_volume                     2123.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9829
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      28.29


_exptl_crystal_description       PLATE
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    2.284
_shelx_estimated_absorpt_T_min   0.494
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5814
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON II'
_diffrn_measurement_method       'narrow frame ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20830
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.597
_diffrn_reflns_theta_max         28.296
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5278
_reflns_number_gt                4879
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+4.2363P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_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         5278
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0614
_refine_ls_wR_factor_gt          0.0603
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_restrained_S_all      1.227
_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
I1 I 0.95342(2) 0.60327(2) 0.99625(2) 0.01781(5) Uani 1 1 d . . . . .
Co1 Co 0.68943(4) 0.59829(2) 0.71140(4) 0.01097(7) Uani 1 1 d . . . . .
O1 O 0.7212(3) 0.72374(6) 0.6391(3) 0.0231(4) Uani 1 1 d . . . . .
O2 O 1.1462(3) 0.69950(7) 0.2905(3) 0.0233(4) Uani 1 1 d . . . . .
N1 N 0.7345(3) 0.65160(7) 0.6209(3) 0.0132(4) Uani 1 1 d . . . . .
N2 N 0.8379(3) 0.65958(7) 0.5285(3) 0.0127(4) Uani 1 1 d . . . . .
C1 C 0.5702(3) 0.63598(8) 0.8103(3) 0.0135(5) Uani 1 1 d . . . . .
C2 C 0.4801(3) 0.62728(9) 0.9144(3) 0.0164(5) Uani 1 1 d . . . . .
H2 H 0.471755 0.599083 0.946829 0.020 Uiso 1 1 calc R U . . .
C3 C 0.4025(3) 0.65921(9) 0.9713(3) 0.0187(6) Uani 1 1 d . . . . .
H3 H 0.338102 0.652221 1.037519 0.022 Uiso 1 1 calc R U . . .
C4 C 0.4177(4) 0.70105(10) 0.9328(4) 0.0215(6) Uani 1 1 d . . . . .
H4 H 0.364883 0.722597 0.972460 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5117(3) 0.71077(9) 0.8354(4) 0.0186(5) Uani 1 1 d . . . . .
H5 H 0.526778 0.739196 0.810374 0.022 Uiso 1 1 calc R U . . .
C6 C 0.5836(3) 0.67851(8) 0.7745(3) 0.0135(5) Uani 1 1 d . . . . .
C7 C 0.5218(3) 0.57334(8) 0.4859(3) 0.0168(5) Uani 1 1 d . . . . .
C8 C 0.4857(3) 0.55638(8) 0.6240(4) 0.0166(5) Uani 1 1 d . . . . .
C9 C 0.6349(3) 0.53548(8) 0.7351(3) 0.0161(5) Uani 1 1 d . . . . .
C10 C 0.7601(3) 0.53683(8) 0.6579(3) 0.0150(5) Uani 1 1 d . . . . .
C11 C 0.6910(3) 0.55997(8) 0.5063(3) 0.0154(5) Uani 1 1 d . . . . .
C12 C 0.4003(4) 0.59793(10) 0.3428(4) 0.0304(7) Uani 1 1 d . . . . .
H12A H 0.459641 0.609497 0.273924 0.046 Uiso 1 1 calc R U . . .
H12B H 0.353420 0.620932 0.388005 0.046 Uiso 1 1 calc R U . . .
H12C H 0.307355 0.579639 0.271830 0.046 Uiso 1 1 calc R U . . .
C13 C 0.6855(3) 0.68812(8) 0.6719(3) 0.0139(5) Uani 1 1 d . . . . .
C14 C 0.7650(3) 0.67654(8) 0.3714(3) 0.0155(5) Uani 1 1 d . . . . .
H14 H 0.644546 0.679596 0.321575 0.019 Uiso 1 1 calc R U . . .
C15 C 0.8603(3) 0.68944(8) 0.2822(3) 0.0173(5) Uani 1 1 d . . . . .
H15 H 0.807056 0.700727 0.170681 0.021 Uiso 1 1 calc R U . . .
C16 C 1.0383(4) 0.68567(8) 0.3587(4) 0.0174(5) Uani 1 1 d . . . . .
C17 C 1.1108(3) 0.66715(9) 0.5199(4) 0.0171(5) Uani 1 1 d . . . . .
H17 H 1.230680 0.663207 0.571755 0.020 Uiso 1 1 calc R U . . .
C18 C 1.0087(3) 0.65468(8) 0.6032(3) 0.0157(5) Uani 1 1 d . . . . .
H18 H 1.058289 0.642570 0.713593 0.019 Uiso 1 1 calc R U . . .
C19 C 0.3153(4) 0.55655(10) 0.6370(5) 0.0282(7) Uani 1 1 d . . . . .
H19A H 0.259015 0.583565 0.596665 0.042 Uiso 1 1 calc R U . . .
H19B H 0.330045 0.552340 0.756089 0.042 Uiso 1 1 calc R U . . .
H19C H 0.244993 0.533861 0.566923 0.042 Uiso 1 1 calc R U . . .
C20 C 0.6537(4) 0.51185(10) 0.8932(4) 0.0278(7) Uani 1 1 d . . . . .
H20A H 0.616499 0.482759 0.863693 0.042 Uiso 1 1 calc R U . . .
H20B H 0.583403 0.525110 0.947554 0.042 Uiso 1 1 calc R U . . .
H20C H 0.773446 0.512198 0.972049 0.042 Uiso 1 1 calc R U . . .
C21 C 0.9302(4) 0.51536(10) 0.7268(4) 0.0257(6) Uani 1 1 d . . . . .
H21A H 0.913643 0.485098 0.734830 0.039 Uiso 1 1 calc R U . . .
H21B H 0.998045 0.526491 0.840240 0.039 Uiso 1 1 calc R U . . .
H21C H 0.989983 0.520444 0.650418 0.039 Uiso 1 1 calc R U . . .
C22 C 0.7729(4) 0.56685(10) 0.3804(4) 0.0263(7) Uani 1 1 d . . . . .
H22A H 0.756056 0.541935 0.308157 0.039 Uiso 1 1 calc R U . . .
H22B H 0.895189 0.571852 0.441615 0.039 Uiso 1 1 calc R U . . .
H22C H 0.720814 0.591270 0.309292 0.039 Uiso 1 1 calc R U . . .
C23 C 1.0733(4) 0.72215(10) 0.1306(4) 0.0273(7) Uani 1 1 d . . . . .
H23A H 1.164977 0.734794 0.103479 0.041 Uiso 1 1 calc R U . . .
H23B H 0.997564 0.744268 0.140729 0.041 Uiso 1 1 calc R U . . .
H23C H 1.008093 0.702680 0.039585 0.041 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
I1 Co1 2.5967(4) . ?
Co1 C1 1.956(3) . ?
Co1 N1 1.962(2) . ?
Co1 C7 2.058(3) . ?
Co1 C9 2.081(3) . ?
Co1 C8 2.083(3) . ?
Co1 C11 2.133(3) . ?
Co1 C10 2.147(3) . ?
O1 C13 1.234(3) . ?
O2 C16 1.334(3) . ?
O2 C23 1.451(4) . ?
N1 C13 1.362(3) . ?
N1 N2 1.408(3) . ?
N2 C14 1.350(3) . ?
N2 C18 1.351(3) . ?
C1 C6 1.402(4) . ?
C1 C2 1.403(4) . ?
C2 C3 1.396(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9500 . ?
C6 C13 1.478(3) . ?
C7 C8 1.429(4) . ?
C7 C11 1.445(4) . ?
C7 C12 1.481(4) . ?
C8 C9 1.421(4) . ?
C8 C19 1.494(4) . ?
C9 C10 1.450(4) . ?
C9 C20 1.494(4) . ?
C10 C11 1.403(4) . ?
C10 C21 1.499(4) . ?
C11 C22 1.499(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 C15 1.368(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.403(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.398(4) . ?
C17 C18 1.372(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C1 Co1 N1 81.31(10) . . ?
C1 Co1 C7 110.48(11) . . ?
N1 Co1 C7 97.96(10) . . ?
C1 Co1 C9 112.14(11) . . ?
N1 Co1 C9 162.66(10) . . ?
C7 Co1 C9 67.60(11) . . ?
C1 Co1 C8 92.87(11) . . ?
N1 Co1 C8 132.49(10) . . ?
C7 Co1 C8 40.35(11) . . ?
C9 Co1 C8 39.92(10) . . ?
C1 Co1 C11 150.39(10) . . ?
N1 Co1 C11 96.37(10) . . ?
C7 Co1 C11 40.28(10) . . ?
C9 Co1 C11 66.48(10) . . ?
C8 Co1 C11 66.88(10) . . ?
C1 Co1 C10 152.07(11) . . ?
N1 Co1 C10 126.40(10) . . ?
C7 Co1 C10 66.45(10) . . ?
C9 Co1 C10 40.07(10) . . ?
C8 Co1 C10 66.54(10) . . ?
C11 Co1 C10 38.28(10) . . ?
C1 Co1 I1 88.05(7) . . ?
N1 Co1 I1 94.81(7) . . ?
C7 Co1 I1 158.84(8) . . ?
C9 Co1 I1 96.50(8) . . ?
C8 Co1 I1 132.30(8) . . ?
C11 Co1 I1 121.52(7) . . ?
C10 Co1 I1 92.38(7) . . ?
C16 O2 C23 117.0(2) . . ?
C13 N1 N2 110.9(2) . . ?
C13 N1 Co1 118.97(17) . . ?
N2 N1 Co1 129.25(16) . . ?
C14 N2 C18 120.8(2) . . ?
C14 N2 N1 118.4(2) . . ?
C18 N2 N1 120.3(2) . . ?
C6 C1 C2 115.9(2) . . ?
C6 C1 Co1 113.67(18) . . ?
C2 C1 Co1 130.4(2) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 123.3(2) . . ?
C5 C6 C13 120.4(2) . . ?
C1 C6 C13 116.2(2) . . ?
C8 C7 C11 107.9(2) . . ?
C8 C7 C12 125.0(3) . . ?
C11 C7 C12 127.0(3) . . ?
C8 C7 Co1 70.77(15) . . ?
C11 C7 Co1 72.64(15) . . ?
C12 C7 Co1 125.1(2) . . ?
C9 C8 C7 107.8(2) . . ?
C9 C8 C19 126.4(3) . . ?
C7 C8 C19 125.4(3) . . ?
C9 C8 Co1 69.95(15) . . ?
C7 C8 Co1 68.88(15) . . ?
C19 C8 Co1 131.8(2) . . ?
C8 C9 C10 107.9(2) . . ?
C8 C9 C20 126.4(3) . . ?
C10 C9 C20 125.4(3) . . ?
C8 C9 Co1 70.14(15) . . ?
C10 C9 Co1 72.42(15) . . ?
C20 C9 Co1 128.3(2) . . ?
C11 C10 C9 108.1(2) . . ?
C11 C10 C21 126.7(3) . . ?
C9 C10 C21 125.1(3) . . ?
C11 C10 Co1 70.32(15) . . ?
C9 C10 Co1 67.51(14) . . ?
C21 C10 Co1 129.7(2) . . ?
C10 C11 C7 108.1(2) . . ?
C10 C11 C22 126.0(3) . . ?
C7 C11 C22 125.8(3) . . ?
C10 C11 Co1 71.40(15) . . ?
C7 C11 Co1 67.08(14) . . ?
C22 C11 Co1 130.56(19) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 N1 125.5(2) . . ?
O1 C13 C6 125.1(2) . . ?
N1 C13 C6 109.4(2) . . ?
N2 C14 C15 121.6(2) . . ?
N2 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C16 118.6(2) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
O2 C16 C17 116.6(2) . . ?
O2 C16 C15 124.6(3) . . ?
C17 C16 C15 118.7(2) . . ?
C18 C17 C16 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
N2 C18 C17 120.1(2) . . ?
N2 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 C20 H20A 109.5 . . ?
C9 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C9 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 C21 H21A 109.5 . . ?
C10 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C10 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 C22 H22A 109.5 . . ?
C11 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C11 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_refine_diff_density_max         0.636
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.089



