# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_190424_pyterpy_cocl_2h2o
_database_code_depnum_ccdc_archive 'CCDC 2059287'
loop_
_audit_author_name
_audit_author_address
'Hikaru Zenno'
;Kumamoto University
Japan
;
_audit_update_record             
;
2021-01-28 deposited with the CCDC.	2021-04-22 downloaded from the CCDC.
;
_audit_creation_date             2020-11-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 Cl2 Co N4, H4 O2'
_chemical_formula_sum            'C20 H18 Cl2 Co N4 O2'
_chemical_formula_weight         476.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Co C N Cl'
_chemical_oxdiff_usercomment     123K
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'

_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      orthorhombic
_space_group_IT_number           54
_space_group_name_H-M_alt        'P c c a'
_space_group_name_Hall           '-P 2a 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x, -y, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   11.1222(8)
_cell_length_b                   7.8437(8)
_cell_length_c                   21.7183(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1894.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2916
_cell_measurement_temperature    173
_cell_measurement_theta_max      29.3240
_cell_measurement_theta_min      3.2530
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.793
_exptl_absorpt_coefficient_mu    1.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.15 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             972
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15667
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         2.597
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00 -51.00   0.50    7.76    --    5.00  45.00 169.56   54
  2  ω     41.00  72.00   0.50    7.76    --    5.00  45.00 169.56   62
  3  ω    -42.00 -17.00   0.50    7.76    --    5.00  45.00  30.00   50
  4  ω    -34.00  35.00   0.50    7.76    --    5.00  45.00 169.56  138
  5  ω    -97.00  68.00   0.50    7.76    --   -8.90  45.00  90.00  330
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0141558000
_diffrn_orient_matrix_UB_12      -0.0487687000
_diffrn_orient_matrix_UB_13      0.0265457000
_diffrn_orient_matrix_UB_21      0.0210604000
_diffrn_orient_matrix_UB_22      -0.0672526000
_diffrn_orient_matrix_UB_23      -0.0190251000
_diffrn_orient_matrix_UB_31      0.0585705000
_diffrn_orient_matrix_UB_32      0.0354839000
_diffrn_orient_matrix_UB_33      0.0005311000
_diffrn_oxdiff_ac4_digest_frames 
;
0166df19e283da73f7fbd59bdcd003213c006347f4e
;
_diffrn_oxdiff_ac4_digest_hkl    
;
01d34b120f8894a8c0d9cf360176fdb2457a4f
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1706
_reflns_number_total             1939
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.004
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1939
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.237
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+4.0046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1240
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: H2A(0.5) H2B(0.5) H1A(0.5) H1B(0.5)
3.a Free rotating group:
 O2(H2A,H2B), O1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C4(H4), C10(H10), C11(H11), C2(H2), C1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.7500 0.5000 0.63301(3) 0.0152(2) Uani 1 2 d S T P . .
Cl1 Cl 0.60807(8) 0.76562(12) 0.62286(4) 0.0183(2) Uani 1 1 d . . . . .
O2 O 0.7500 0.0000 0.52473(17) 0.0270(9) Uani 1 2 d GS T P . .
H2A H 0.7157 -0.0597 0.5523 0.040 Uiso 0.5 1 d G U P . .
H2B H 0.7950 0.0679 0.5447 0.040 Uiso 0.5 1 d G U P . .
N3 N 0.7500 0.5000 0.22359(18) 0.0149(9) Uani 1 2 d S T P . .
O1 O 0.7500 1.0000 0.72636(19) 0.0362(11) Uani 1 2 d GS T P . .
H1A H 0.7984 1.0340 0.6987 0.054 Uiso 0.5 1 d G U P . .
H1B H 0.7154 0.9138 0.7106 0.054 Uiso 0.5 1 d G U P . .
N1 N 0.6123(3) 0.3446(4) 0.62044(12) 0.0176(7) Uani 1 1 d . . . . .
N2 N 0.7500 0.5000 0.54753(18) 0.0161(9) Uani 1 2 d S T P . .
C6 C 0.6662(3) 0.4091(5) 0.51774(15) 0.0146(7) Uani 1 1 d . . . . .
C7 C 0.6643(3) 0.4054(5) 0.45419(15) 0.0159(8) Uani 1 1 d . . . . .
H7 H 0.6057 0.3397 0.4330 0.019 Uiso 1 1 calc R U . . .
C9 C 0.7500 0.5000 0.3530(2) 0.0168(10) Uani 1 2 d S T P . .
C5 C 0.5853(3) 0.3186(5) 0.56022(16) 0.0162(8) Uani 1 1 d . . . . .
C3 C 0.4240(3) 0.1332(5) 0.58680(17) 0.0198(8) Uani 1 1 d . . . . .
H3 H 0.3592 0.0608 0.5754 0.024 Uiso 1 1 calc R U . . .
C4 C 0.4920(3) 0.2146(5) 0.54236(16) 0.0175(8) Uani 1 1 d . . . . .
H4 H 0.4744 0.1988 0.4999 0.021 Uiso 1 1 calc R U . . .
C8 C 0.7500 0.5000 0.4213(2) 0.0161(11) Uani 1 2 d S T P . .
C10 C 0.6670(3) 0.4053(5) 0.31957(16) 0.0219(9) Uani 1 1 d . . . . .
H10 H 0.6086 0.3382 0.3403 0.026 Uiso 1 1 calc R U . . .
C11 C 0.6699(3) 0.4090(5) 0.25608(16) 0.0228(9) Uani 1 1 d . . . . .
H11 H 0.6121 0.3436 0.2342 0.027 Uiso 1 1 calc R U . . .
C2 C 0.4521(3) 0.1591(5) 0.64838(17) 0.0207(8) Uani 1 1 d . . . . .
H2 H 0.4071 0.1046 0.6799 0.025 Uiso 1 1 calc R U . . .
C1 C 0.5463(3) 0.2653(5) 0.66287(16) 0.0196(8) Uani 1 1 d . . . . .
H1 H 0.5652 0.2828 0.7051 0.024 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
Co1 Cl1 2.6232(9) . ?
Co1 Cl1 2.6232(9) 2_665 ?
Co1 N3 1.967(4) 7_566 ?
Co1 N1 1.976(3) . ?
Co1 N1 1.976(3) 2_665 ?
Co1 N2 1.856(4) . ?
O2 H2A 0.8501 . ?
O2 H2B 0.8501 . ?
N3 Co1 1.967(4) 7_565 ?
N3 C11 1.342(4) . ?
N3 C11 1.342(4) 2_665 ?
O1 H1A 0.8500 . ?
O1 H1B 0.8500 . ?
N1 C5 1.357(4) . ?
N1 C1 1.332(5) . ?
N2 C6 1.340(4) . ?
N2 C6 1.340(4) 2_665 ?
C6 C7 1.381(5) . ?
C6 C5 1.471(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.404(4) . ?
C9 C8 1.482(6) . ?
C9 C10 1.390(4) 2_665 ?
C9 C10 1.390(4) . ?
C5 C4 1.377(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(5) . ?
C3 C2 1.388(5) . ?
C4 H4 0.9500 . ?
C8 C7 1.404(4) 2_665 ?
C10 H10 0.9500 . ?
C10 C11 1.380(5) . ?
C11 H11 0.9500 . ?
C2 H2 0.9500 . ?
C2 C1 1.374(5) . ?
C1 H1 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
Cl1 Co1 Cl1 170.36(4) 2_665 . ?
N3 Co1 Cl1 94.82(2) 7_566 . ?
N3 Co1 Cl1 94.82(2) 7_566 2_665 ?
N3 Co1 N1 97.94(8) 7_566 2_665 ?
N3 Co1 N1 97.94(8) 7_566 . ?
N1 Co1 Cl1 87.99(9) 2_665 . ?
N1 Co1 Cl1 90.68(9) . . ?
N1 Co1 Cl1 90.68(9) 2_665 2_665 ?
N1 Co1 Cl1 88.00(9) . 2_665 ?
N1 Co1 N1 164.13(16) . 2_665 ?
N2 Co1 Cl1 85.18(2) . . ?
N2 Co1 Cl1 85.18(2) . 2_665 ?
N2 Co1 N3 180.0 . 7_566 ?
N2 Co1 N1 82.06(8) . 2_665 ?
N2 Co1 N1 82.06(8) . . ?
H2A O2 H2B 104.5 . . ?
C11 N3 Co1 121.7(2) . 7_565 ?
C11 N3 Co1 121.7(2) 2_665 7_565 ?
C11 N3 C11 116.6(4) 2_665 . ?
H1A O1 H1B 104.5 . . ?
C5 N1 Co1 113.4(2) . . ?
C1 N1 Co1 128.3(2) . . ?
C1 N1 C5 118.3(3) . . ?
C6 N2 Co1 118.9(2) . . ?
C6 N2 Co1 118.9(2) 2_665 . ?
C6 N2 C6 122.3(4) . 2_665 ?
N2 C6 C7 120.3(3) . . ?
N2 C6 C5 112.3(3) . . ?
C7 C6 C5 127.4(3) . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.2(3) . . ?
C8 C7 H7 120.4 . . ?
C10 C9 C8 121.5(2) . . ?
C10 C9 C8 121.5(2) 2_665 . ?
C10 C9 C10 117.0(5) 2_665 . ?
N1 C5 C6 113.4(3) . . ?
N1 C5 C4 121.8(3) . . ?
C4 C5 C6 124.8(3) . . ?
C4 C3 H3 120.6 . . ?
C4 C3 C2 118.8(4) . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C7 C8 C7 118.7(4) . 2_665 ?
C7 C8 C9 120.6(2) . . ?
C7 C8 C9 120.6(2) 2_665 . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.7(4) . . ?
C11 C10 H10 120.1 . . ?
N3 C11 C10 123.5(4) . . ?
N3 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
C3 C2 H2 120.6 . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 H2 120.6 . . ?
N1 C1 C2 123.0(3) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?

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 N3 C11 C10 179.9(3) 7_565 . . . ?
Co1 N1 C5 C6 1.2(4) . . . . ?
Co1 N1 C5 C4 -179.8(3) . . . . ?
Co1 N1 C1 C2 -179.9(3) . . . . ?
Co1 N2 C6 C7 -179.5(2) . . . . ?
Co1 N2 C6 C5 -0.7(3) . . . . ?
Cl1 Co1 N2 C6 89.72(17) . . . 2_665 ?
Cl1 Co1 N2 C6 -90.28(17) 2_665 . . 2_665 ?
Cl1 Co1 N2 C6 89.72(17) 2_665 . . . ?
Cl1 Co1 N2 C6 -90.28(17) . . . . ?
N1 Co1 N2 C6 -178.9(2) 2_665 . . . ?
N1 Co1 N2 C6 1.1(2) 2_665 . . 2_665 ?
N1 Co1 N2 C6 1.1(2) . . . . ?
N1 Co1 N2 C6 -178.9(2) . . . 2_665 ?
N1 C5 C4 C3 -0.4(6) . . . . ?
N2 C6 C7 C8 -0.9(5) . . . . ?
N2 C6 C5 N1 -0.4(4) . . . . ?
N2 C6 C5 C4 -179.3(3) . . . . ?
C6 N2 C6 C7 0.5(2) 2_665 . . . ?
C6 N2 C6 C5 179.3(3) 2_665 . . . ?
C6 C7 C8 C7 0.5(2) . . . 2_665 ?
C6 C7 C8 C9 -179.5(2) . . . . ?
C6 C5 C4 C3 178.4(3) . . . . ?
C7 C6 C5 N1 178.3(3) . . . . ?
C7 C6 C5 C4 -0.6(6) . . . . ?
C9 C10 C11 N3 0.3(6) . . . . ?
C5 N1 C1 C2 -0.3(6) . . . . ?
C5 C6 C7 C8 -179.6(3) . . . . ?
C3 C2 C1 N1 -0.1(6) . . . . ?
C4 C3 C2 C1 0.2(6) . . . . ?
C8 C9 C10 C11 179.9(3) . . . . ?
C10 C9 C8 C7 -0.9(3) . . . . ?
C10 C9 C8 C7 -1.0(3) 2_665 . . 2_665 ?
C10 C9 C8 C7 179.0(3) . . . 2_665 ?
C10 C9 C8 C7 179.0(3) 2_665 . . . ?
C10 C9 C10 C11 -0.1(3) 2_665 . . . ?
C11 N3 C11 C10 -0.1(3) 2_665 . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C1 N1 C5 C6 -178.4(3) . . . . ?
C1 N1 C5 C4 0.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.521
_oxdiff_exptl_absorpt_empirical_full_min 0.431
####################################################################### 
# 
# 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_210105_pyterpycoclhs_2
_database_code_depnum_ccdc_archive 'CCDC 2059289'
loop_
_audit_author_name
_audit_author_address
'Hikaru Zenno'
;Kumamoto University
Japan
;
_audit_update_record             
;
2021-01-28 deposited with the CCDC.	2021-04-22 downloaded from the CCDC.
;
_audit_creation_date             2021-01-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 Cl2 Co N4, H4 O2'
_chemical_formula_sum            'C20 H18 Cl2 Co N4 O2'
_chemical_formula_weight         476.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Co N C H O'
_chemical_oxdiff_usercomment     '250 K'
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'

_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      orthorhombic
_space_group_IT_number           54
_space_group_name_H-M_alt        'P c c a'
_space_group_name_Hall           '-P 2a 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x, -y, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   10.7848(18)
_cell_length_b                   7.5554(18)
_cell_length_c                   21.527(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1754.1(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    619
_cell_measurement_temperature    250
_cell_measurement_theta_max      25.2700
_cell_measurement_theta_min      2.6820
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.560
_exptl_absorpt_coefficient_mu    1.311
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.15 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             972
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1008
_diffrn_reflns_av_unetI/netI     0.1063
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8067
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.674
_diffrn_ambient_temperature      250
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  39.00   0.50  105.00    --   20.00  54.00-150.00  106
  2  ω     63.00  90.00   0.50  105.00    --   20.00  54.00-150.00   54
  3  ω    -73.00 -32.00   0.50  105.00    --   20.00  54.00 -90.00   82
  4  ω    -24.00  30.00   0.50  105.00    --   20.00  54.00 -90.00  108
  5  ω     83.00 110.00   0.50  105.00    --   20.00  54.00 -90.00   54
  6  ω    -52.00 -27.00   0.50  105.00    --   20.00  54.00 -60.00   50
  7  ω    -21.00   6.00   0.50  105.00    --   20.00  54.00 -60.00   54
  8  ω    -67.00  23.00   0.50  105.00    --   20.00  54.00 -30.00  180
  9  ω    -71.00 -43.00   0.50  105.00    --   20.00  54.00-150.00   56
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0035045000
_diffrn_orient_matrix_UB_12      0.0933242000
_diffrn_orient_matrix_UB_13      0.0032476000
_diffrn_orient_matrix_UB_21      -0.0019062000
_diffrn_orient_matrix_UB_22      0.0092349000
_diffrn_orient_matrix_UB_23      -0.0327743000
_diffrn_orient_matrix_UB_31      -0.0656288000
_diffrn_orient_matrix_UB_32      0.0047337000
_diffrn_orient_matrix_UB_33      0.0010718000
_diffrn_oxdiff_ac4_digest_frames 
;
019c3d8ba86c467764afb6ecd4f735051400744b4cc
;
_diffrn_oxdiff_ac4_digest_hkl    
;
018967a02be97c3c7867138772e9eea4805069
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                943
_reflns_number_total             1799
_reflns_odcompleteness_completeness 98.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.557
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1799
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1678
_refine_ls_R_factor_gt           0.0891
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1274P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2017
_refine_ls_wR_factor_ref         0.2397
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: H2A(0.5) H2B(0.5) H1A(0.5) H1B(0.5)
3.a Free rotating group:
 O2(H2A,H2B), O1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C3(H3), C10(H10), C2(H2), C11(H11), C1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.7500 0.5000 0.36625(6) 0.0410(5) Uani 1 2 d S T P . .
Cl00 Cl 0.88670(19) 0.7518(3) 0.37107(8) 0.0479(7) Uani 1 1 d . . . . .
N2 N 0.7500 0.5000 0.4577(4) 0.042(2) Uani 1 2 d S T P . .
N3 N 0.7500 0.5000 0.7718(4) 0.040(2) Uani 1 2 d S T P . .
N1 N 0.6046(6) 0.6657(9) 0.3879(3) 0.0394(16) Uani 1 1 d . . . . .
C5 C 0.5829(7) 0.6837(10) 0.4464(3) 0.0356(18) Uani 1 1 d . . . . .
C9 C 0.7500 0.5000 0.6462(5) 0.040(3) Uani 1 2 d S T P . .
C7 C 0.6652(7) 0.5934(10) 0.5479(3) 0.0374(18) Uani 1 1 d . . . . .
H7 H 0.6048 0.6603 0.5688 0.045 Uiso 1 1 calc R U . . .
C8 C 0.7500 0.5000 0.5802(4) 0.038(3) Uani 1 2 d S T P . .
C6 C 0.6677(7) 0.5903(11) 0.4863(3) 0.0384(19) Uani 1 1 d . . . . .
C4 C 0.4908(7) 0.7831(10) 0.4681(4) 0.045(2) Uani 1 1 d . . . . .
H4 H 0.4761 0.7920 0.5110 0.054 Uiso 1 1 calc R U . . .
C3 C 0.4201(8) 0.8693(11) 0.4278(4) 0.050(2) Uani 1 1 d . . . . .
H3 H 0.3544 0.9406 0.4418 0.060 Uiso 1 1 calc R U . . .
C10 C 0.8324(8) 0.4117(12) 0.6792(4) 0.058(3) Uani 1 1 d . . . . .
H10 H 0.8944 0.3459 0.6590 0.070 Uiso 1 1 calc R U . . .
C2 C 0.4431(7) 0.8537(11) 0.3680(4) 0.046(2) Uani 1 1 d . . . . .
H2 H 0.3954 0.9163 0.3388 0.055 Uiso 1 1 calc R U . . .
C11 C 0.8285(9) 0.4152(13) 0.7395(4) 0.064(3) Uani 1 1 d . . . . .
H11 H 0.8887 0.3494 0.7610 0.077 Uiso 1 1 calc R U . . .
C1 C 0.5346(7) 0.7483(12) 0.3493(3) 0.048(2) Uani 1 1 d . . . . .
H1 H 0.5485 0.7338 0.3065 0.057 Uiso 1 1 calc R U . . .
O2 O 0.2500 1.0000 0.5375(4) 0.057(2) Uani 1 2 d GS T P . .
H2A H 0.2075 1.0404 0.5682 0.086 Uiso 0.5 1 d G U P . .
H2B H 0.2561 0.8884 0.5447 0.086 Uiso 0.5 1 d G U P . .
O1 O 0.2500 1.0000 0.2301(5) 0.103(4) Uani 1 2 d GS T P . .
H1A H 0.2038 0.9464 0.2035 0.154 Uiso 0.5 1 d G U P . .
H1B H 0.2940 1.0715 0.2082 0.154 Uiso 0.5 1 d G U 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
Co1 Cl00 2.409(2) 2_665 ?
Co1 Cl00 2.409(2) . ?
Co1 N2 1.967(8) . ?
Co1 N3 2.033(8) 7_565 ?
Co1 N1 2.060(6) 2_665 ?
Co1 N1 2.060(6) . ?
N2 C6 1.278(8) . ?
N2 C6 1.278(8) 2_665 ?
N3 Co1 2.033(8) 7_566 ?
N3 C11 1.269(9) 2_665 ?
N3 C11 1.269(9) . ?
N1 C5 1.287(8) . ?
N1 C1 1.284(9) . ?
C5 C6 1.439(10) . ?
C5 C4 1.331(10) . ?
C9 C8 1.420(13) . ?
C9 C10 1.319(9) . ?
C9 C10 1.319(9) 2_665 ?
C7 H7 0.9400 . ?
C7 C8 1.348(9) . ?
C7 C6 1.326(9) . ?
C8 C7 1.349(9) 2_665 ?
C4 H4 0.9400 . ?
C4 C3 1.325(10) . ?
C3 H3 0.9400 . ?
C3 C2 1.317(10) . ?
C10 H10 0.9400 . ?
C10 C11 1.298(10) . ?
C2 H2 0.9400 . ?
C2 C1 1.330(11) . ?
C11 H11 0.9400 . ?
C1 H1 0.9400 . ?
O2 H2A 0.8605 . ?
O2 H2B 0.8601 . ?
O1 H1A 0.8601 . ?
O1 H1B 0.8600 . ?

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
Cl00 Co1 Cl00 175.06(10) . 2_665 ?
N2 Co1 Cl00 87.53(5) . 2_665 ?
N2 Co1 Cl00 87.53(5) . . ?
N2 Co1 N3 180.0 . 7_565 ?
N2 Co1 N1 76.93(17) . . ?
N2 Co1 N1 76.92(17) . 2_665 ?
N3 Co1 Cl00 92.47(5) 7_565 2_665 ?
N3 Co1 Cl00 92.47(5) 7_565 . ?
N3 Co1 N1 103.08(17) 7_565 2_665 ?
N3 Co1 N1 103.07(17) 7_565 . ?
N1 Co1 Cl00 90.3(2) . 2_665 ?
N1 Co1 Cl00 88.6(2) . . ?
N1 Co1 Cl00 90.3(2) 2_665 . ?
N1 Co1 Cl00 88.6(2) 2_665 2_665 ?
N1 Co1 N1 153.8(3) 2_665 . ?
C6 N2 Co1 118.8(5) 2_665 . ?
C6 N2 Co1 118.8(5) . . ?
C6 N2 C6 122.4(9) . 2_665 ?
C11 N3 Co1 123.2(5) 2_665 7_566 ?
C11 N3 Co1 123.2(5) . 7_566 ?
C11 N3 C11 113.5(9) 2_665 . ?
C5 N1 Co1 115.1(5) . . ?
C1 N1 Co1 126.6(5) . . ?
C1 N1 C5 118.3(7) . . ?
N1 C5 C6 114.6(7) . . ?
N1 C5 C4 122.6(7) . . ?
C4 C5 C6 122.8(7) . . ?
C10 C9 C8 122.6(5) 2_665 . ?
C10 C9 C8 122.6(5) . . ?
C10 C9 C10 114.7(10) 2_665 . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.6(7) . . ?
C7 C8 C9 121.1(5) . . ?
C7 C8 C9 121.1(5) 2_665 . ?
C7 C8 C7 117.8(9) . 2_665 ?
N2 C6 C5 114.5(7) . . ?
N2 C6 C7 120.3(8) . . ?
C7 C6 C5 125.2(7) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 C5 118.5(8) . . ?
C3 C4 H4 120.8 . . ?
C4 C3 H3 120.4 . . ?
C2 C3 C4 119.2(8) . . ?
C2 C3 H3 120.4 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.5(9) . . ?
C11 C10 H10 119.8 . . ?
C3 C2 H2 120.4 . . ?
C3 C2 C1 119.2(8) . . ?
C1 C2 H2 120.4 . . ?
N3 C11 C10 125.4(9) . . ?
N3 C11 H11 117.3 . . ?
C10 C11 H11 117.3 . . ?
N1 C1 C2 122.2(7) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
H2A O2 H2B 104.5 . . ?
H1A O1 H1B 104.5 . . ?

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 N2 C6 C5 -0.1(7) . . . . ?
Co1 N2 C6 C7 -179.9(5) . . . . ?
Co1 N3 C11 C10 -179.7(8) 7_566 . . . ?
Co1 N1 C5 C6 2.5(9) . . . . ?
Co1 N1 C5 C4 -178.6(6) . . . . ?
Co1 N1 C1 C2 -179.6(6) . . . . ?
N1 C5 C6 N2 -1.6(10) . . . . ?
N1 C5 C6 C7 178.2(8) . . . . ?
N1 C5 C4 C3 -1.2(12) . . . . ?
C5 N1 C1 C2 1.5(12) . . . . ?
C5 C4 C3 C2 0.1(13) . . . . ?
C9 C10 C11 N3 -0.5(16) . . . . ?
C8 C9 C10 C11 -179.8(7) . . . . ?
C8 C7 C6 N2 -0.2(11) . . . . ?
C8 C7 C6 C5 180.0(6) . . . . ?
C6 N2 C6 C5 179.9(7) 2_665 . . . ?
C6 N2 C6 C7 0.1(5) 2_665 . . . ?
C6 C5 C4 C3 177.6(7) . . . . ?
C6 C7 C8 C9 -179.9(5) . . . . ?
C6 C7 C8 C7 0.1(5) . . . 2_665 ?
C4 C5 C6 N2 179.5(7) . . . . ?
C4 C5 C6 C7 -0.8(13) . . . . ?
C4 C3 C2 C1 1.7(13) . . . . ?
C3 C2 C1 N1 -2.6(13) . . . . ?
C10 C9 C8 C7 0.8(6) 2_665 . . . ?
C10 C9 C8 C7 0.8(6) . . . 2_665 ?
C10 C9 C8 C7 -179.2(6) . . . . ?
C10 C9 C8 C7 -179.2(6) 2_665 . . 2_665 ?
C10 C9 C10 C11 0.2(7) 2_665 . . . ?
C11 N3 C11 C10 0.3(8) 2_665 . . . ?
C1 N1 C5 C6 -178.5(7) . . . . ?
C1 N1 C5 C4 0.5(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.732
_oxdiff_exptl_absorpt_empirical_full_min 0.586
####################################################################### 
# 
# 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_181115_pyterpy_a_cocl_a_solv
_database_code_depnum_ccdc_archive 'CCDC 2059290'
loop_
_audit_author_name
_audit_author_address
'Hikaru Zenno'
;Kumamoto University
Japan
;
_audit_update_record             
;
2021-01-28 deposited with the CCDC.	2021-04-22 downloaded from the CCDC.
;
_audit_creation_date             2021-01-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 Cl2 Co N4'
_chemical_formula_sum            'C22 H14 Cl2 Co N4'
_chemical_formula_weight         464.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22N4CoH14Cl2
_chemical_oxdiff_usercomment     173K
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'

_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           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   8.6789(5)
_cell_length_b                   13.8285(5)
_cell_length_c                   10.2562(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.332(7)
_cell_angle_gamma                90
_cell_volume                     1130.25(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3556
_cell_measurement_temperature    173
_cell_measurement_theta_max      30.5140
_cell_measurement_theta_min      2.6230
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.824
_exptl_absorpt_coefficient_mu    1.010
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.15 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             470
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8936
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_min         2.617
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  32.00   0.50   35.45    --   20.00  54.00  60.00  104
  2  ω    -70.00  68.00   0.50   35.45    --   20.00  54.00 -30.00  276
  3  ω     76.00 110.00   0.50   35.45    --   20.00  54.00 -30.00   68
  4  ω    -66.00 -40.00   0.50   35.45    --   20.00  54.00  90.00   52
  5  ω     17.00  42.00   0.50   35.45    --   20.00  54.00  90.00   50
  6  ω     46.00  72.00   0.50   35.45    --   20.00  54.00  90.00   52
  7  ω    -65.00 -36.00   0.50   35.45    --   20.00  54.00 -60.00   58
  8  ω     -6.00  19.00   0.50   35.45    --   20.00  54.00 -60.00   50
  9  ω    -66.00 -38.00   0.50   35.45    --   20.00  54.00 120.00   56
 10  ω    -73.00 -47.00   0.50   35.45    --   20.00  54.00-120.00   52
 11  ω    -24.00 109.00   0.50   35.45    --   20.00  54.00-120.00  266
 12  ω    -69.00 -42.00   0.50   35.45    --   20.00  54.00  60.00   54
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0401294000
_diffrn_orient_matrix_UB_12      -0.0289193000
_diffrn_orient_matrix_UB_13      -0.0344839000
_diffrn_orient_matrix_UB_21      0.0269955000
_diffrn_orient_matrix_UB_22      0.0423969000
_diffrn_orient_matrix_UB_23      -0.0237409000
_diffrn_orient_matrix_UB_31      0.0746835000
_diffrn_orient_matrix_UB_32      0.0001770000
_diffrn_orient_matrix_UB_33      0.0625543000
_diffrn_oxdiff_ac4_digest_frames 
;
0196724d66216e4d6252ce8b1c85a71ea0011380995
;
_diffrn_oxdiff_ac4_digest_hkl    
;
01fb9cd24627b01b8cc16da7aeed3baf1673aa
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1803
_reflns_number_total             2296
_reflns_odcompleteness_completeness 98.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+0.6013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0763
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: C14(0.5) H14(0.5) C12(0.5) H12(0.5) C13(0.5) H13(0.5) C15(0.5)
 H15(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C3(H3), C2(H2), C1(H1), C14(H14), C12(H12), C13(H13), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.7500 0.71254(3) 0.2500 0.01745(12) Uani 1 2 d S T P . .
Cl1 Cl 0.73769(6) 0.71517(4) 0.48357(5) 0.02369(14) Uani 1 1 d . . . . .
N2 N 0.7500 0.56360(15) 0.2500 0.0165(5) Uani 1 2 d S T P . .
N1 N 0.4856(2) 0.67562(12) 0.15787(18) 0.0186(4) Uani 1 1 d . . . . .
N3 N 0.7500 -0.13140(16) 0.2500 0.0226(6) Uani 1 2 d S T P . .
C6 C 0.6034(2) 0.51611(13) 0.1998(2) 0.0168(4) Uani 1 1 d . . . . .
C5 C 0.4530(2) 0.57945(13) 0.1487(2) 0.0170(4) Uani 1 1 d . . . . .
C4 C 0.2904(3) 0.54368(15) 0.0958(2) 0.0221(5) Uani 1 1 d . . . . .
H4 H 0.2705 0.4760 0.0886 0.027 Uiso 1 1 calc R U . . .
C8 C 0.7500 0.36523(19) 0.2500 0.0195(6) Uani 1 2 d S T P . .
C7 C 0.5981(3) 0.41556(14) 0.1981(2) 0.0191(4) Uani 1 1 d . . . . .
H7 H 0.4940 0.3821 0.1626 0.023 Uiso 1 1 calc R U . . .
C3 C 0.1574(3) 0.60844(15) 0.0535(2) 0.0252(5) Uani 1 1 d . . . . .
H3 H 0.0450 0.5855 0.0181 0.030 Uiso 1 1 calc R U . . .
C9 C 0.7500 0.2608(2) 0.2500 0.0233(7) Uani 1 2 d S T P . .
C2 C 0.1901(3) 0.70655(15) 0.0634(2) 0.0247(5) Uani 1 1 d . . . . .
H2 H 0.1010 0.7522 0.0351 0.030 Uiso 1 1 calc R U . . .
C11 C 0.7500 0.0714(2) 0.2500 0.0252(7) Uani 1 2 d S T P . .
C1 C 0.3555(3) 0.73672(15) 0.1154(2) 0.0224(5) Uani 1 1 d . . . . .
H1 H 0.3778 0.8042 0.1213 0.027 Uiso 1 1 calc R U . . .
C10 C 0.7500 0.1747(2) 0.2500 0.0274(7) Uani 1 2 d S T P A .
C14 C 0.8302(7) 0.0194(3) 0.1797(6) 0.0377(12) Uani 0.5 1 d . . P A 1
H14 H 0.8881 0.0521 0.1311 0.045 Uiso 0.5 1 calc R U P A 1
C12 C 0.6579(6) 0.0183(3) 0.1280(5) 0.0298(11) Uani 0.5 1 d . . P A 2
H12 H 0.5905 0.0507 0.0428 0.036 Uiso 0.5 1 calc R U P A 2
C13 C 0.6649(6) -0.0815(3) 0.1315(5) 0.0286(10) Uani 0.5 1 d . . P A 2
H13 H 0.6068 -0.1161 0.0460 0.034 Uiso 0.5 1 calc R U P A 2
C15 C 0.8252(6) -0.0802(3) 0.1809(5) 0.0323(11) Uani 0.5 1 d . . P A 1
H15 H 0.8782 -0.1146 0.1298 0.039 Uiso 0.5 1 calc R U 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 Cl1 2.4400(5) 2_655 ?
Co1 Cl1 2.4401(5) . ?
Co1 N2 2.060(2) . ?
Co1 N1 2.1685(16) . ?
Co1 N1 2.1685(16) 2_655 ?
Co1 N3 2.158(2) 1_565 ?
N2 C6 1.340(2) . ?
N2 C6 1.340(2) 2_655 ?
N1 C5 1.355(2) . ?
N1 C1 1.338(2) . ?
N3 Co1 2.158(2) 1_545 ?
N3 C13 1.337(5) 2_655 ?
N3 C13 1.337(5) . ?
N3 C15 1.340(5) . ?
N3 C15 1.340(5) 2_655 ?
C6 C5 1.485(3) . ?
C6 C7 1.391(3) . ?
C5 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.388(3) . ?
C8 C7 1.397(2) 2_655 ?
C8 C7 1.397(2) . ?
C8 C9 1.444(4) . ?
C7 H7 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.382(3) . ?
C9 C10 1.191(4) . ?
C2 H2 0.9500 . ?
C2 C1 1.383(3) . ?
C11 C10 1.428(4) . ?
C11 C14 1.386(5) 2_655 ?
C11 C14 1.386(5) . ?
C11 C12 1.397(5) 2_655 ?
C11 C12 1.397(5) . ?
C1 H1 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.378(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(6) . ?
C13 H13 0.9500 . ?
C15 H15 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
Cl1 Co1 Cl1 178.29(3) 2_655 . ?
N2 Co1 Cl1 90.855(15) . . ?
N2 Co1 Cl1 90.855(15) . 2_655 ?
N2 Co1 N1 76.38(4) . 2_655 ?
N2 Co1 N1 76.38(4) . . ?
N2 Co1 N3 180.0 . 1_565 ?
N1 Co1 Cl1 91.49(5) . 2_655 ?
N1 Co1 Cl1 88.91(5) 2_655 2_655 ?
N1 Co1 Cl1 91.49(5) 2_655 . ?
N1 Co1 Cl1 88.91(5) . . ?
N1 Co1 N1 152.76(9) 2_655 . ?
N3 Co1 Cl1 89.145(15) 1_565 2_655 ?
N3 Co1 Cl1 89.145(15) 1_565 . ?
N3 Co1 N1 103.62(4) 1_565 2_655 ?
N3 Co1 N1 103.62(4) 1_565 . ?
C6 N2 Co1 119.35(11) 2_655 . ?
C6 N2 Co1 119.35(11) . . ?
C6 N2 C6 121.3(2) 2_655 . ?
C5 N1 Co1 114.65(13) . . ?
C1 N1 Co1 127.19(14) . . ?
C1 N1 C5 118.11(17) . . ?
C13 N3 Co1 121.1(2) . 1_545 ?
C13 N3 Co1 121.1(2) 2_655 1_545 ?
C13 N3 C13 117.8(4) . 2_655 ?
C15 N3 Co1 121.9(2) 2_655 1_545 ?
C15 N3 Co1 121.9(2) . 1_545 ?
C15 N3 C15 116.2(4) 2_655 . ?
N2 C6 C5 114.50(16) . . ?
N2 C6 C7 121.11(18) . . ?
C7 C6 C5 124.38(18) . . ?
N1 C5 C6 115.10(16) . . ?
N1 C5 C4 121.95(18) . . ?
C4 C5 C6 122.95(17) . . ?
C5 C4 H4 120.5 . . ?
C5 C4 C3 118.92(18) . . ?
C3 C4 H4 120.5 . . ?
C7 C8 C7 120.2(2) 2_655 . ?
C7 C8 C9 119.89(12) . . ?
C7 C8 C9 119.89(12) 2_655 . ?
C6 C7 C8 118.13(19) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C4 C3 H3 120.3 . . ?
C2 C3 C4 119.31(19) . . ?
C2 C3 H3 120.3 . . ?
C10 C9 C8 180.0 . . ?
C3 C2 H2 120.8 . . ?
C3 C2 C1 118.4(2) . . ?
C1 C2 H2 120.8 . . ?
C14 C11 C10 121.3(2) . . ?
C14 C11 C10 121.3(2) 2_655 . ?
C14 C11 C14 117.5(4) 2_655 . ?
C12 C11 C10 121.7(2) 2_655 . ?
C12 C11 C10 121.7(2) . . ?
C12 C11 C12 116.6(4) . 2_655 ?
N1 C1 C2 123.27(19) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C9 C10 C11 180.0 . . ?
C11 C14 H14 120.3 . . ?
C15 C14 C11 119.3(4) . . ?
C15 C14 H14 120.3 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.9(4) . . ?
C13 C12 H12 120.0 . . ?
N3 C13 C12 122.8(4) . . ?
N3 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
N3 C15 C14 123.8(4) . . ?
N3 C15 H15 118.1 . . ?
C14 C15 H15 118.1 . . ?

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 C6 C5 -0.21(19) . . . . ?
Co1 N2 C6 C7 -179.92(14) . . . . ?
Co1 N1 C5 C6 -1.5(2) . . . . ?
Co1 N1 C5 C4 178.30(15) . . . . ?
Co1 N1 C1 C2 -177.02(16) . . . . ?
Co1 N3 C13 C12 178.1(3) 1_545 . . . ?
Co1 N3 C15 C14 -179.1(4) 1_545 . . . ?
N2 C6 C5 N1 1.1(2) . . . . ?
N2 C6 C5 C4 -178.62(17) . . . . ?
N2 C6 C7 C8 -0.2(3) . . . . ?
N1 C5 C4 C3 -1.2(3) . . . . ?
C6 N2 C6 C5 179.79(19) 2_655 . . . ?
C6 N2 C6 C7 0.08(14) 2_655 . . . ?
C6 C5 C4 C3 178.5(2) . . . . ?
C5 N1 C1 C2 0.3(3) . . . . ?
C5 C6 C7 C8 -179.83(16) . . . . ?
C5 C4 C3 C2 0.9(3) . . . . ?
C4 C3 C2 C1 0.0(3) . . . . ?
C7 C6 C5 N1 -179.18(18) . . . . ?
C7 C6 C5 C4 1.1(3) . . . . ?
C7 C8 C7 C6 0.08(13) 2_655 . . . ?
C3 C2 C1 N1 -0.6(3) . . . . ?
C9 C8 C7 C6 -179.92(13) . . . . ?
C11 C14 C15 N3 -1.8(8) . . . . ?
C11 C12 C13 N3 3.8(7) . . . . ?
C1 N1 C5 C6 -179.10(17) . . . . ?
C1 N1 C5 C4 0.7(3) . . . . ?
C10 C11 C14 C15 -179.2(4) . . . . ?
C10 C11 C12 C13 178.2(3) . . . . ?
C14 C11 C14 C15 0.8(4) 2_655 . . . ?
C12 C11 C12 C13 -1.8(3) 2_655 . . . ?
C13 N3 C13 C12 -1.9(3) 2_655 . . . ?
C15 N3 C15 C14 0.9(4) 2_655 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.075
_oxdiff_exptl_absorpt_empirical_full_min 0.910
####################################################################### 
# 
# 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_201024_pyterpyacocl
_database_code_depnum_ccdc_archive 'CCDC 2059288'
loop_
_audit_author_name
_audit_author_address
'Hikaru Zenno'
;Kumamoto University
Japan
;
_audit_update_record             
;
2021-01-28 deposited with the CCDC.	2021-04-22 downloaded from the CCDC.
;
_audit_creation_date             2020-11-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 Cl2 Co N4, 2(O), H2 O'
_chemical_formula_sum            'C22 H16 Cl2 Co N4 O3'
_chemical_formula_weight         514.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Co Cl'
_chemical_oxdiff_usercomment     '123 K'
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'

_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           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   8.377(2)
_cell_length_b                   13.222(3)
_cell_length_c                   9.678(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.06(4)
_cell_angle_gamma                90
_cell_volume                     978.8(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    763
_cell_measurement_temperature    123
_cell_measurement_theta_max      21.2480
_cell_measurement_theta_min      2.7060
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    1.186
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.15 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             522
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0903
_diffrn_reflns_av_unetI/netI     0.1149
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7361
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.720
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00 -24.00   0.50   50.00    --   20.00  54.00 150.00   94
  2  ω     -1.00  25.00   0.50   50.00    --   20.00  54.00 150.00   52
  3  ω    -72.00 -37.00   0.50   50.00    --   20.00  54.00  60.00   70
  4  ω    -10.00 109.00   0.50   50.00    --   20.00  54.00  60.00  238
  5  ω    -71.00  74.00   0.50   50.00    --   20.00  54.00   0.00  290
  6  ω    -66.00 -27.00   0.50   50.00    --   20.00  54.00  90.00   78
  7  ω     29.00  53.50   0.50   50.00    --   20.00  54.00  90.00   49
  8  ω    -21.00  94.00   0.50   50.00    --   20.00  54.00 -90.00  230
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0079429000
_diffrn_orient_matrix_UB_12      0.0529287000
_diffrn_orient_matrix_UB_13      0.0075939000
_diffrn_orient_matrix_UB_21      -0.0651247000
_diffrn_orient_matrix_UB_22      -0.0085713000
_diffrn_orient_matrix_UB_23      0.0278222000
_diffrn_orient_matrix_UB_31      0.0654635000
_diffrn_orient_matrix_UB_32      -0.0022216000
_diffrn_orient_matrix_UB_33      0.0749053000
_diffrn_oxdiff_ac4_digest_frames 
;
013f715786893cf68c20c2a6586980595e011011323
;
_diffrn_oxdiff_ac4_digest_hkl    
;
01b2b7a7931ef977493a3f0cbe1c4116066cde
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1109
_reflns_number_total             1994
_reflns_odcompleteness_completeness 98.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         1994
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0558
_refine_ls_restrained_S_all      0.995
_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)+(0.0550P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1372
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Sof(C13)=Sof(H13)=Sof(C12)=Sof(H12)=1-FVAR(1)
 Sof(C15)=Sof(H15)=Sof(C14)=Sof(H14)=FVAR(1)
 Fixed Sof: O1(0.25) O2(0.25) O3(0.5) H3A(0.5) H3B(0.5) O4(0.5)
3.a Free rotating group:
 O3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C3(H3), C1(H1), C2(H2), C15(H15), C14(H14), C13(H13), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.2500 0.28353(7) 0.2500 0.0274(3) Uani 1 2 d S T P . .
Cl1 Cl 0.24063(15) 0.28323(10) 0.49128(13) 0.0306(4) Uani 1 1 d . . . . .
N2 N 0.2500 0.4328(4) 0.2500 0.0259(14) Uani 1 2 d S T P . .
N1 N 0.5133(5) 0.3202(3) 0.3417(4) 0.0244(10) Uani 1 1 d . . . . .
N3 N 0.2500 1.1310(4) 0.2500 0.0236(14) Uani 1 2 d S T P . .
C6 C 0.3963(6) 0.4808(4) 0.2996(5) 0.0230(11) Uani 1 1 d . . . . .
C8 C 0.2500 0.6325(5) 0.2500 0.0254(17) Uani 1 2 d S T P . .
C7 C 0.4005(6) 0.5808(4) 0.3001(5) 0.0255(12) Uani 1 1 d . . . . .
H7 H 0.5068 0.6149 0.3348 0.031 Uiso 1 1 calc R U . . .
C5 C 0.5474(6) 0.4168(4) 0.3506(5) 0.0261(12) Uani 1 1 d . . . . .
C4 C 0.7080(6) 0.4523(4) 0.4029(5) 0.0262(12) Uani 1 1 d . . . . .
H4 H 0.7279 0.5217 0.4096 0.031 Uiso 1 1 calc R U . . .
C3 C 0.8408(6) 0.3884(4) 0.4459(6) 0.0287(12) Uani 1 1 d . . . . .
H3 H 0.9552 0.4120 0.4822 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2500 0.8222(6) 0.2500 0.0283(18) Uani 1 2 d S T P B .
C1 C 0.6425(6) 0.2595(4) 0.3831(5) 0.0287(13) Uani 1 1 d . . . . .
H1 H 0.6205 0.1904 0.3759 0.034 Uiso 1 1 calc R U . . .
C2 C 0.8084(6) 0.2911(4) 0.4363(6) 0.0286(12) Uani 1 1 d . . . . .
H2 H 0.8996 0.2447 0.4662 0.034 Uiso 1 1 calc R U . . .
C9 C 0.2500 0.7362(6) 0.2500 0.0277(17) Uani 1 2 d S T P . .
C11 C 0.2500 0.9270(6) 0.2500 0.0330(19) Uani 1 2 d S T P . .
O1 O 1.548(3) -0.038(3) -0.897(4) 0.098(9) Uani 0.25 1 d . . P A -1
C15 C 0.3418(11) 1.0783(7) 0.1944(10) 0.028(3) Uani 0.549(7) 1 d . . P B -1
H15 H 0.4079 1.1133 0.1528 0.034 Uiso 0.549(7) 1 calc R U P B -1
C14 C 0.3469(13) 0.9788(7) 0.1933(11) 0.033(3) Uani 0.549(7) 1 d . . P B -1
H14 H 0.4165 0.9451 0.1539 0.039 Uiso 0.549(7) 1 calc R U P B -1
C13 C 0.1599(16) 1.0800(9) 0.1297(14) 0.034(3) Uani 0.451(7) 1 d . . P B -2
H13 H 0.0948 1.1153 0.0415 0.041 Uiso 0.451(7) 1 calc R U P B -2
C12 C 0.1552(16) 0.9782(9) 0.1253(15) 0.037(4) Uani 0.451(7) 1 d . . P B -2
H12 H 0.0867 0.9444 0.0365 0.045 Uiso 0.451(7) 1 calc R U P B -2
O2 O 0.954(5) 0.045(3) 1.391(6) 0.18(2) Uani 0.25 1 d . . P C 1
O3 O 0.1930(18) 0.1477(6) 0.729(3) 0.082(5) Uani 0.5 1 d G . P D -2
H3A H 0.2278 0.1717 0.6644 0.123 Uiso 0.5 1 d G U P D -2
H3B H 0.1670 0.1993 0.7677 0.123 Uiso 0.5 1 d G U P D -2
O4 O 0.238(6) -0.0449(11) 0.696(3) 0.173(11) Uani 0.5 1 d . . P E -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
Co1 Cl1 2.3681(13) 2 ?
Co1 Cl1 2.3681(13) . ?
Co1 N2 1.973(5) . ?
Co1 N1 2.072(4) 2 ?
Co1 N1 2.072(4) . ?
Co1 N3 2.017(6) 1_545 ?
N2 C6 1.287(5) 2 ?
N2 C6 1.287(5) . ?
N1 C5 1.303(6) . ?
N1 C1 1.274(6) . ?
N3 Co1 2.017(6) 1_565 ?
N3 C15 1.306(9) . ?
N3 C13 1.290(12) . ?
C6 C7 1.323(6) . ?
C6 C5 1.433(6) . ?
C8 C7 1.339(5) 2 ?
C8 C7 1.339(5) . ?
C8 C9 1.372(10) . ?
C7 H7 0.9300 . ?
C5 C4 1.316(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.322(6) . ?
C3 H3 0.9300 . ?
C3 C2 1.310(6) . ?
C10 C9 1.137(9) . ?
C10 C11 1.385(10) . ?
C1 H1 0.9300 . ?
C1 C2 1.337(7) . ?
C2 H2 0.9300 . ?
C11 C14 1.339(10) . ?
C11 C12 1.329(13) . ?
C15 H15 0.9300 . ?
C15 C14 1.316(11) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.347(15) . ?
C12 H12 0.9300 . ?
O3 H3A 0.8504 . ?
O3 H3B 0.8501 . ?

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
Cl1 Co1 Cl1 179.81(8) 2 . ?
N2 Co1 Cl1 90.09(4) . 2 ?
N2 Co1 Cl1 90.10(4) . . ?
N2 Co1 N1 76.45(11) . . ?
N2 Co1 N1 76.45(11) . 2 ?
N2 Co1 N3 180.0 . 1_545 ?
N1 Co1 Cl1 88.02(11) . 2 ?
N1 Co1 Cl1 92.03(11) 2 2 ?
N1 Co1 Cl1 92.03(11) . . ?
N1 Co1 Cl1 88.02(11) 2 . ?
N1 Co1 N1 152.9(2) 2 . ?
N3 Co1 Cl1 89.90(4) 1_545 . ?
N3 Co1 Cl1 89.91(4) 1_545 2 ?
N3 Co1 N1 103.55(11) 1_545 . ?
N3 Co1 N1 103.55(11) 1_545 2 ?
C6 N2 Co1 119.6(3) . . ?
C6 N2 Co1 119.6(3) 2 . ?
C6 N2 C6 120.9(6) 2 . ?
C5 N1 Co1 115.1(3) . . ?
C1 N1 Co1 127.3(4) . . ?
C1 N1 C5 117.5(4) . . ?
C15 N3 Co1 122.3(4) . 1_565 ?
C13 N3 Co1 121.5(6) . 1_565 ?
N2 C6 C7 121.0(5) . . ?
N2 C6 C5 114.2(5) . . ?
C7 C6 C5 124.8(4) . . ?
C7 C8 C7 118.6(7) 2 . ?
C7 C8 C9 120.7(3) 2 . ?
C7 C8 C9 120.7(3) . . ?
C6 C7 C8 119.3(5) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
N1 C5 C6 114.6(4) . . ?
N1 C5 C4 122.5(5) . . ?
C4 C5 C6 122.9(5) . . ?
C5 C4 H4 120.3 . . ?
C5 C4 C3 119.3(5) . . ?
C3 C4 H4 120.3 . . ?
C4 C3 H3 120.6 . . ?
C2 C3 C4 118.8(5) . . ?
C2 C3 H3 120.6 . . ?
C9 C10 C11 180.0 . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.7(5) . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 119.1(5) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C10 C9 C8 180.0 . . ?
C14 C11 C10 120.8(5) . . ?
C12 C11 C10 120.7(6) . . ?
N3 C15 H15 117.9 . . ?
N3 C15 C14 124.3(8) . . ?
C14 C15 H15 117.9 . . ?
C11 C14 H14 120.6 . . ?
C15 C14 C11 118.8(9) . . ?
C15 C14 H14 120.6 . . ?
N3 C13 H13 118.3 . . ?
N3 C13 C12 123.4(11) . . ?
C12 C13 H13 118.3 . . ?
C11 C12 C13 118.8(11) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
H3A O3 H3B 104.5 . . ?

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 N2 C6 C7 179.5(3) . . . . ?
Co1 N2 C6 C5 0.1(5) . . . . ?
Co1 N1 C5 C6 1.9(5) . . . . ?
Co1 N1 C5 C4 -178.4(4) . . . . ?
Co1 N1 C1 C2 177.6(3) . . . . ?
Co1 N3 C15 C14 179.4(7) 1_565 . . . ?
Co1 N3 C13 C12 -179.4(8) 1_565 . . . ?
N2 C6 C7 C8 0.9(6) . . . . ?
N2 C6 C5 N1 -1.3(6) . . . . ?
N2 C6 C5 C4 178.9(4) . . . . ?
N1 C5 C4 C3 1.2(7) . . . . ?
N1 C1 C2 C3 -0.5(8) . . . . ?
N3 C15 C14 C11 1.3(14) . . . . ?
N3 C13 C12 C11 -1.2(16) . . . . ?
C6 N2 C6 C7 -0.5(3) 2 . . . ?
C6 N2 C6 C5 -179.9(5) 2 . . . ?
C6 C5 C4 C3 -179.0(5) . . . . ?
C7 C6 C5 N1 179.3(4) . . . . ?
C7 C6 C5 C4 -0.5(8) . . . . ?
C7 C8 C7 C6 -0.5(3) 2 . . . ?
C5 N1 C1 C2 1.1(7) . . . . ?
C5 C6 C7 C8 -179.7(4) . . . . ?
C5 C4 C3 C2 -0.6(7) . . . . ?
C4 C3 C2 C1 0.3(8) . . . . ?
C10 C11 C14 C15 179.4(7) . . . . ?
C10 C11 C12 C13 -179.5(8) . . . . ?
C1 N1 C5 C6 178.8(4) . . . . ?
C1 N1 C5 C4 -1.4(7) . . . . ?
C9 C8 C7 C6 179.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.306
_oxdiff_exptl_absorpt_empirical_full_min 0.818
