# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1527563'
loop_
_audit_author_name
_audit_author_address
'Anjana S'
;IIT Bombay
India
;
_audit_update_record             
;
2020-01-03 deposited with the CCDC.	2020-01-09 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 H19 Co I2 N3 O'
_chemical_formula_weight         618.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   12.9288(3)
_cell_length_b                   9.5177(2)
_cell_length_c                   18.2171(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.7800(10)
_cell_angle_gamma                90
_cell_volume                     2122.32(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5244
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      25.2

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_F_000             1180
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    3.730
_shelx_estimated_absorpt_T_min   0.456
_shelx_estimated_absorpt_T_max   0.605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_T_max  0.54
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14811
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.362
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3735
_reflns_number_gt                3188
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_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)+(0.0268P)²+2.9845P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3735
_refine_ls_number_parameters     256
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0654
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.059
_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
C1 C 0.4042(4) 1.2205(5) 0.3545(2) 0.0503(10) Uani 1 1 d . . . . .
H1 H 0.355687 1.295385 0.339434 0.060 Uiso 1 1 calc R U . . .
C2 C 0.4863(4) 1.2264(5) 0.4251(3) 0.0601(13) Uani 1 1 d . . . . .
H2 H 0.492415 1.303917 0.457245 0.072 Uiso 1 1 calc R U . . .
C3 C 0.5585(4) 1.1178(6) 0.4474(3) 0.0618(13) Uani 1 1 d . . . . .
H3 H 0.613586 1.119949 0.495082 0.074 Uiso 1 1 calc R U . . .
C4 C 0.5487(3) 1.0045(5) 0.3981(2) 0.0528(11) Uani 1 1 d . . . . .
H4 H 0.598300 0.930567 0.411447 0.063 Uiso 1 1 calc R U . . .
C5 C 0.4639(3) 1.0031(4) 0.3287(2) 0.0385(9) Uani 1 1 d . . . . .
C6 C 0.4430(3) 0.8819(4) 0.2733(2) 0.0389(9) Uani 1 1 d . . . . .
H6A H 0.471145 0.902599 0.231143 0.047 Uiso 1 1 calc R U . . .
H6B H 0.479120 0.798131 0.299741 0.047 Uiso 1 1 calc R U . . .
C7 C 0.2870(3) 0.7716(4) 0.1722(2) 0.0399(9) Uani 1 1 d . . . . .
H7A H 0.296226 0.672976 0.186312 0.048 Uiso 1 1 calc R U . . .
H7B H 0.331032 0.792321 0.139367 0.048 Uiso 1 1 calc R U . . .
C8 C 0.1690(3) 0.8014(4) 0.1292(2) 0.0418(9) Uani 1 1 d . . . . .
C9 C 0.1000(4) 0.7020(5) 0.0833(2) 0.0562(12) Uani 1 1 d . . . . .
H9 H 0.124946 0.611990 0.078279 0.067 Uiso 1 1 calc R U . . .
C10 C -0.0070(4) 0.7398(6) 0.0451(3) 0.0696(15) Uani 1 1 d . . . . .
H10 H -0.054501 0.675990 0.012489 0.084 Uiso 1 1 calc R U . . .
C11 C -0.0425(4) 0.8696(6) 0.0551(3) 0.0723(15) Uani 1 1 d . . . . .
H11 H -0.115025 0.894818 0.031023 0.087 Uiso 1 1 calc R U . . .
C12 C 0.0302(4) 0.9638(5) 0.1015(3) 0.0609(13) Uani 1 1 d . . . . .
H12 H 0.005187 1.052840 0.108376 0.073 Uiso 1 1 calc R U . . .
C13 C 0.2821(3) 0.8031(4) 0.3030(2) 0.0337(8) Uani 1 1 d . . . . .
C14 C 0.3179(3) 0.6737(4) 0.3363(2) 0.0464(10) Uani 1 1 d . . . . .
H14 H 0.366984 0.622093 0.319371 0.056 Uiso 1 1 calc R U . . .
C15 C 0.2821(4) 0.6204(5) 0.3938(3) 0.0556(11) Uani 1 1 d . . . . .
H15 H 0.307715 0.534048 0.416206 0.067 Uiso 1 1 calc R U . . .
C16 C 0.2093(4) 0.6940(5) 0.4180(3) 0.0567(12) Uani 1 1 d . . . . .
H16 H 0.184520 0.657074 0.456567 0.068 Uiso 1 1 calc R U . . .
C17 C 0.1715(3) 0.8229(5) 0.3860(2) 0.0517(11) Uani 1 1 d . . . . .
H17 H 0.121637 0.872700 0.402933 0.062 Uiso 1 1 calc R U . . .
C18 C 0.2083(3) 0.8782(4) 0.3283(2) 0.0389(9) Uani 1 1 d . . . . .
C19 C 0.1136(18) 1.0932(15) 0.3307(12) 0.082(5) Uani 0.65(3) 1 d D U P A 1
H19A H 0.045581 1.045605 0.323613 0.123 Uiso 0.65(3) 1 calc R U P A 1
H19B H 0.099592 1.183513 0.306004 0.123 Uiso 0.65(3) 1 calc R U P A 1
H19C H 0.151158 1.105337 0.385141 0.123 Uiso 0.65(3) 1 calc R U P A 1
O1 O 0.180(2) 1.012(3) 0.2972(15) 0.046(4) Uani 0.65(3) 1 d D U P A 1
C19' C 0.066(2) 1.064(3) 0.287(3) 0.081(7) Uani 0.35(3) 1 d D U P A 2
H19D H 0.009791 0.993851 0.271868 0.121 Uiso 0.35(3) 1 calc R U P A 2
H19E H 0.049151 1.138470 0.249285 0.121 Uiso 0.35(3) 1 calc R U P A 2
H19F H 0.071633 1.100428 0.336776 0.121 Uiso 0.35(3) 1 calc R U P A 2
O1' O 0.169(4) 1.001(5) 0.290(3) 0.051(7) Uani 0.35(3) 1 d D U P A 2
N1 N 0.3924(2) 1.1095(3) 0.30691(17) 0.0377(7) Uani 1 1 d . . . . .
N2 N 0.3227(2) 0.8592(3) 0.24262(16) 0.0312(6) Uani 1 1 d . . . . .
N3 N 0.1349(3) 0.9328(3) 0.13700(18) 0.0407(8) Uani 1 1 d . . . . .
Co1 Co 0.25789(4) 1.07007(5) 0.20472(3) 0.03524(13) Uani 1 1 d D . . . .
I1 I 0.35866(2) 1.09246(3) 0.09150(2) 0.04757(10) Uani 1 1 d . . . . .
I2 I 0.16974(3) 1.32850(3) 0.17989(2) 0.06631(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.344(5) . ?
C1 C2 1.380(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(6) . ?
C4 H4 0.9300 . ?
C5 N1 1.342(5) . ?
C5 C6 1.499(5) . ?
C6 N2 1.490(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.474(5) . ?
C7 C8 1.500(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N3 1.349(5) . ?
C8 C9 1.382(5) . ?
C9 C10 1.381(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.350(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(7) . ?
C11 H11 0.9300 . ?
C12 N3 1.332(5) . ?
C12 H12 0.9300 . ?
C13 C18 1.384(5) . ?
C13 C14 1.385(5) . ?
C13 N2 1.463(4) . ?
C14 C15 1.372(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.355(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(6) . ?
C17 H17 0.9300 . ?
C18 O1' 1.38(3) . ?
C18 O1 1.392(17) . ?
C19 O1 1.429(13) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O1 Co1 2.295(7) . ?
C19' O1' 1.438(18) . ?
C19' H19D 0.9600 . ?
C19' H19E 0.9600 . ?
C19' H19F 0.9600 . ?
O1' Co1 2.300(14) . ?
N1 Co1 2.132(3) . ?
N2 Co1 2.198(3) . ?
N3 Co1 2.119(3) . ?
Co1 I2 2.6873(6) . ?
Co1 I1 2.7797(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.7(4) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 119.1(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 118.8(4) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 122.2(4) . . ?
N1 C5 C6 115.1(3) . . ?
C4 C5 C6 122.8(4) . . ?
N2 C6 C5 107.7(3) . . ?
N2 C6 H6A 110.2 . . ?
C5 C6 H6A 110.2 . . ?
N2 C6 H6B 110.2 . . ?
C5 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
N2 C7 C8 109.2(3) . . ?
N2 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
N2 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
N3 C8 C9 122.0(4) . . ?
N3 C8 C7 115.6(3) . . ?
C9 C8 C7 122.4(4) . . ?
C10 C9 C8 118.2(5) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C11 C10 C9 120.0(5) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.0(5) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
N3 C12 C11 122.8(5) . . ?
N3 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
C18 C13 C14 118.8(4) . . ?
C18 C13 N2 120.9(3) . . ?
C14 C13 N2 120.3(3) . . ?
C15 C14 C13 121.1(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.7(4) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 119.8(4) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
O1' C18 C13 116.7(9) . . ?
O1' C18 C17 123.3(7) . . ?
C13 C18 C17 119.8(4) . . ?
C13 C18 O1 117.2(5) . . ?
C17 C18 O1 122.8(5) . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 O1 C19 116.1(8) . . ?
C18 O1 Co1 113.4(7) . . ?
C19 O1 Co1 130.4(11) . . ?
O1' C19' H19D 109.5 . . ?
O1' C19' H19E 109.5 . . ?
H19D C19' H19E 109.5 . . ?
O1' C19' H19F 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
C18 O1' C19' 124(2) . . ?
C18 O1' Co1 113.8(12) . . ?
C19' O1' Co1 120.8(19) . . ?
C5 N1 C1 118.6(3) . . ?
C5 N1 Co1 114.6(2) . . ?
C1 N1 Co1 126.3(3) . . ?
C13 N2 C7 111.1(3) . . ?
C13 N2 C6 110.8(3) . . ?
C7 N2 C6 113.9(3) . . ?
C13 N2 Co1 112.1(2) . . ?
C7 N2 Co1 105.2(2) . . ?
C6 N2 Co1 103.4(2) . . ?
C12 N3 C8 118.0(4) . . ?
C12 N3 Co1 127.0(3) . . ?
C8 N3 Co1 115.1(2) . . ?
N3 Co1 N1 149.84(12) . . ?
N3 Co1 N2 76.05(11) . . ?
N1 Co1 N2 76.41(12) . . ?
N3 Co1 O1 81.5(9) . . ?
N1 Co1 O1 80.2(9) . . ?
N2 Co1 O1 76.2(4) . . ?
N3 Co1 O1' 76.8(18) . . ?
N1 Co1 O1' 84.7(17) . . ?
N2 Co1 O1' 75.6(8) . . ?
N3 Co1 I2 105.55(9) . . ?
N1 Co1 I2 99.70(9) . . ?
N2 Co1 I2 170.55(8) . . ?
O1 Co1 I2 94.7(4) . . ?
O1' Co1 I2 95.6(9) . . ?
N3 Co1 I1 93.34(9) . . ?
N1 Co1 I1 100.89(8) . . ?
N2 Co1 I1 94.63(7) . . ?
O1 Co1 I1 170.3(6) . . ?
O1' Co1 I1 167.4(15) . . ?
I2 Co1 I1 94.569(18) . . ?

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
N1 C1 C2 C3 0.6(7) . . . . ?
C1 C2 C3 C4 0.9(7) . . . . ?
C2 C3 C4 C5 -1.9(6) . . . . ?
C3 C4 C5 N1 1.5(6) . . . . ?
C3 C4 C5 C6 -176.8(4) . . . . ?
N1 C5 C6 N2 -39.3(4) . . . . ?
C4 C5 C6 N2 139.1(4) . . . . ?
N2 C7 C8 N3 30.1(4) . . . . ?
N2 C7 C8 C9 -151.1(4) . . . . ?
N3 C8 C9 C10 -0.4(6) . . . . ?
C7 C8 C9 C10 -179.1(4) . . . . ?
C8 C9 C10 C11 -2.1(7) . . . . ?
C9 C10 C11 C12 2.2(8) . . . . ?
C10 C11 C12 N3 0.3(8) . . . . ?
C18 C13 C14 C15 -0.6(6) . . . . ?
N2 C13 C14 C15 179.0(4) . . . . ?
C13 C14 C15 C16 1.0(7) . . . . ?
C14 C15 C16 C17 -0.8(7) . . . . ?
C15 C16 C17 C18 0.1(7) . . . . ?
C14 C13 C18 O1' -175(3) . . . . ?
N2 C13 C18 O1' 5(3) . . . . ?
C14 C13 C18 C17 -0.1(6) . . . . ?
N2 C13 C18 C17 -179.6(3) . . . . ?
C14 C13 C18 O1 175.9(17) . . . . ?
N2 C13 C18 O1 -3.6(17) . . . . ?
C16 C17 C18 O1' 175(4) . . . . ?
C16 C17 C18 C13 0.4(6) . . . . ?
C16 C17 C18 O1 -175.4(18) . . . . ?
C13 C18 O1 C19 -172.9(19) . . . . ?
C17 C18 O1 C19 3(3) . . . . ?
C13 C18 O1 Co1 3(2) . . . . ?
C17 C18 O1 Co1 178.9(7) . . . . ?
C13 C18 O1' C19' 156(4) . . . . ?
C17 C18 O1' C19' -19(7) . . . . ?
C13 C18 O1' Co1 -10(5) . . . . ?
C17 C18 O1' Co1 175.4(14) . . . . ?
C4 C5 N1 C1 -0.1(5) . . . . ?
C6 C5 N1 C1 178.4(3) . . . . ?
C4 C5 N1 Co1 -172.5(3) . . . . ?
C6 C5 N1 Co1 6.0(4) . . . . ?
C2 C1 N1 C5 -1.0(6) . . . . ?
C2 C1 N1 Co1 170.4(3) . . . . ?
C18 C13 N2 C7 -115.2(4) . . . . ?
C14 C13 N2 C7 65.3(4) . . . . ?
C18 C13 N2 C6 117.2(4) . . . . ?
C14 C13 N2 C6 -62.3(4) . . . . ?
C18 C13 N2 Co1 2.2(4) . . . . ?
C14 C13 N2 Co1 -177.3(3) . . . . ?
C8 C7 N2 C13 76.5(4) . . . . ?
C8 C7 N2 C6 -157.6(3) . . . . ?
C8 C7 N2 Co1 -45.1(3) . . . . ?
C5 C6 N2 C13 -70.2(4) . . . . ?
C5 C6 N2 C7 163.8(3) . . . . ?
C5 C6 N2 Co1 50.2(3) . . . . ?
C11 C12 N3 C8 -2.8(7) . . . . ?
C11 C12 N3 Co1 176.3(4) . . . . ?
C9 C8 N3 C12 2.8(6) . . . . ?
C7 C8 N3 C12 -178.4(4) . . . . ?
C9 C8 N3 Co1 -176.3(3) . . . . ?
C7 C8 N3 Co1 2.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 I2 0.93 3.13 3.762(5) 126.4 . yes
C4 H4 I1 0.93 3.27 4.087(5) 147.9 2_645 yes
C6 H6A I1 0.97 3.08 3.721(4) 125.2 . yes
C6 H6B I1 0.97 3.08 4.020(4) 164.0 2_645 yes
C7 H7B I1 0.97 3.04 3.637(4) 121.0 . yes
C9 H9 I2 0.93 3.22 3.940(5) 136.0 1_545 yes
C11 H11 I1 0.93 3.22 4.116(5) 161.6 3_575 yes
C19^a H19B^a I2 0.96 3.06 3.792(12) 134.4 . yes
C19'^b H19D^b I2 0.96 3.15 3.99(2) 146.1 2_545 yes
C19'^b H19E^b I2 0.96 2.93 3.69(2) 136.9 . yes
C1 H1 I2 0.93 3.13 3.762(5) 126.4 . yes
C4 H4 I1 0.93 3.27 4.087(5) 147.9 2_645 yes
C6 H6A I1 0.97 3.08 3.721(4) 125.2 . yes
C6 H6B I1 0.97 3.08 4.020(4) 164.0 2_645 yes
C7 H7B I1 0.97 3.04 3.637(4) 121.0 . yes
C9 H9 I2 0.93 3.22 3.940(5) 136.0 1_545 yes
C11 H11 I1 0.93 3.22 4.116(5) 161.6 3_575 yes
C19^a H19B^a I2 0.96 3.06 3.792(12) 134.4 . yes
C19'^b H19D^b I2 0.96 3.15 3.99(2) 146.1 2_545 yes
C19'^b H19E^b I2 0.96 2.93 3.69(2) 136.9 . yes

_refine_diff_density_max         0.798
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_MN
_database_code_depnum_ccdc_archive 'CCDC 1532216'
loop_
_audit_author_name
_audit_author_address
'Anjana S'
;IIT Bombay
India
;
_audit_update_record             
;
2020-01-03 deposited with the CCDC.	2020-01-09 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 H20 Cl2 Mn N3 O1.50'
_chemical_formula_weight         440.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   9.6360(3)
_cell_length_b                   13.9208(4)
_cell_length_c                   15.4915(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2078.04(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4777
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      26.12

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.907
_shelx_estimated_absorpt_T_min   0.742
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9091
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.489
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3654
_reflns_number_gt                3345
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0276P)²+0.0888P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.013(19)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3654
_refine_ls_number_parameters     246
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0564
_refine_ls_wR_factor_gt          0.0544
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.040
_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
C1 C 0.3822(3) 0.0654(3) 0.7599(2) 0.0557(9) Uani 1 1 d . . . . .
H1 H 0.421267 0.004356 0.757213 0.067 Uiso 1 1 calc R U . . .
C2 C 0.4633(4) 0.1408(3) 0.7863(2) 0.0709(11) Uani 1 1 d . . . . .
H2 H 0.555140 0.130676 0.802324 0.085 Uiso 1 1 calc R U . . .
C3 C 0.4077(4) 0.2310(3) 0.7889(2) 0.0777(12) Uani 1 1 d . . . . .
H3 H 0.461283 0.283010 0.806541 0.093 Uiso 1 1 calc R U . . .
C4 C 0.2713(4) 0.2441(3) 0.7651(2) 0.0602(10) Uani 1 1 d . . . . .
H4 H 0.232079 0.305155 0.765603 0.072 Uiso 1 1 calc R U . . .
C5 C 0.1934(3) 0.1653(2) 0.74030(19) 0.0416(7) Uani 1 1 d . . . . .
C6 C 0.0419(3) 0.1740(2) 0.72033(19) 0.0445(8) Uani 1 1 d . . . . .
H6A H -0.011842 0.160159 0.771812 0.053 Uiso 1 1 calc R U . . .
H6B H 0.021230 0.239231 0.702498 0.053 Uiso 1 1 calc R U . . .
C7 C -0.1480(3) 0.0817(2) 0.6520(2) 0.0419(7) Uani 1 1 d . . . . .
H7A H -0.202382 0.135036 0.630138 0.050 Uiso 1 1 calc R U . . .
H7B H -0.177729 0.068111 0.710540 0.050 Uiso 1 1 calc R U . . .
C8 C -0.1692(3) -0.0054(2) 0.5959(2) 0.0423(7) Uani 1 1 d . . . . .
C9 C -0.2765(4) -0.0119(3) 0.5364(3) 0.0664(11) Uani 1 1 d . . . . .
H9 H -0.339893 0.037998 0.529942 0.080 Uiso 1 1 calc R U . . .
C10 C -0.2865(5) -0.0937(3) 0.4874(3) 0.0840(14) Uani 1 1 d . . . . .
H10 H -0.357040 -0.099675 0.446793 0.101 Uiso 1 1 calc R U . . .
C11 C -0.1933(5) -0.1664(3) 0.4983(2) 0.0721(12) Uani 1 1 d . . . . .
H11 H -0.199629 -0.222461 0.465972 0.086 Uiso 1 1 calc R U . . .
C12 C -0.0901(4) -0.1547(2) 0.5580(2) 0.0521(8) Uani 1 1 d . . . . .
H12 H -0.025889 -0.203925 0.565053 0.062 Uiso 1 1 calc R U . . .
C13 C 0.0413(3) 0.14193(19) 0.56504(18) 0.0357(7) Uani 1 1 d . . . . .
C14 C -0.0199(4) 0.2232(2) 0.5318(2) 0.0512(8) Uani 1 1 d . . . . .
H14 H -0.081778 0.258284 0.565401 0.061 Uiso 1 1 calc R U . . .
C15 C 0.0100(4) 0.2532(3) 0.4485(2) 0.0610(9) Uani 1 1 d . . . . .
H15 H -0.033522 0.307113 0.425558 0.073 Uiso 1 1 calc R U . . .
C16 C 0.1045(4) 0.2027(2) 0.4002(2) 0.0535(8) Uani 1 1 d . . . . .
H16 H 0.124947 0.223048 0.344451 0.064 Uiso 1 1 calc R U . . .
C17 C 0.1695(3) 0.1226(2) 0.4328(2) 0.0470(8) Uani 1 1 d . . . . .
H17 H 0.233935 0.089383 0.399572 0.056 Uiso 1 1 calc R U . . .
C18 C 0.1378(3) 0.0917(2) 0.51612(18) 0.0367(7) Uani 1 1 d . . . . .
C19 C 0.2995(5) -0.0384(3) 0.5049(3) 0.0917(15) Uani 1 1 d . . . . .
H19A H 0.258031 -0.064098 0.453468 0.137 Uiso 1 1 calc R U . . .
H19B H 0.336324 -0.090011 0.539064 0.137 Uiso 1 1 calc R U . . .
H19C H 0.372969 0.004808 0.489456 0.137 Uiso 1 1 calc R U . . .
N1 N 0.2472(2) 0.07664(18) 0.73741(15) 0.0425(6) Uani 1 1 d . . . . .
N2 N 0.0022(2) 0.10652(16) 0.65086(14) 0.0344(5) Uani 1 1 d . . . . .
N3 N -0.0771(2) -0.07597(16) 0.60666(14) 0.0383(6) Uani 1 1 d . . . . .
O1 O 0.1970(2) 0.01199(14) 0.55347(13) 0.0466(5) Uani 1 1 d . . . . .
Cl2 Cl 0.23788(8) -0.18200(5) 0.68575(5) 0.0514(2) Uani 1 1 d . . . . .
Cl3 Cl -0.02106(8) -0.05088(5) 0.82842(4) 0.0476(2) Uani 1 1 d . . . . .
Mn1 Mn 0.10331(4) -0.03933(3) 0.69275(2) 0.03409(12) Uani 1 1 d . . . . .
O2 O 0.6510(9) -0.0469(7) 0.8244(7) 0.182(4) Uani 0.5 1 d . 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
C1 N1 1.356(4) . ?
C1 C2 1.372(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9300 . ?
C5 N1 1.339(4) . ?
C5 C6 1.498(4) . ?
C6 N2 1.479(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.488(4) . ?
C7 C8 1.505(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N3 1.334(4) . ?
C8 C9 1.388(5) . ?
C9 C10 1.373(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(5) . ?
C11 H11 0.9300 . ?
C12 N3 1.336(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(4) . ?
C13 C18 1.389(4) . ?
C13 N2 1.467(3) . ?
C14 C15 1.387(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.394(4) . ?
C17 H17 0.9300 . ?
C18 O1 1.375(3) . ?
C19 O1 1.426(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N1 Mn1 2.238(2) . ?
N2 Mn1 2.344(2) . ?
N3 Mn1 2.250(2) . ?
O1 Mn1 2.446(2) . ?
Cl2 Mn1 2.3745(8) . ?
Cl3 Mn1 2.4248(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.3(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.2(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 122.0(3) . . ?
N1 C5 C6 116.4(3) . . ?
C4 C5 C6 121.5(3) . . ?
N2 C6 C5 110.6(2) . . ?
N2 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
N2 C7 C8 108.2(2) . . ?
N2 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
N2 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
N3 C8 C9 122.1(3) . . ?
N3 C8 C7 115.5(2) . . ?
C9 C8 C7 122.4(3) . . ?
C10 C9 C8 118.2(3) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 118.3(3) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
N3 C12 C11 123.2(3) . . ?
N3 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
C14 C13 C18 119.8(3) . . ?
C14 C13 N2 120.4(3) . . ?
C18 C13 N2 119.8(2) . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 119.4(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
O1 C18 C13 117.0(2) . . ?
O1 C18 C17 123.2(3) . . ?
C13 C18 C17 119.7(3) . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C5 N1 C1 118.0(3) . . ?
C5 N1 Mn1 115.78(19) . . ?
C1 N1 Mn1 126.2(2) . . ?
C13 N2 C6 112.3(2) . . ?
C13 N2 C7 109.8(2) . . ?
C6 N2 C7 113.0(2) . . ?
C13 N2 Mn1 115.80(16) . . ?
C6 N2 Mn1 103.95(17) . . ?
C7 N2 Mn1 101.52(16) . . ?
C8 N3 C12 118.1(3) . . ?
C8 N3 Mn1 114.91(18) . . ?
C12 N3 Mn1 126.4(2) . . ?
C18 O1 C19 117.5(2) . . ?
C18 O1 Mn1 116.98(16) . . ?
C19 O1 Mn1 125.26(19) . . ?
N1 Mn1 N3 145.66(9) . . ?
N1 Mn1 N2 73.64(9) . . ?
N3 Mn1 N2 73.20(8) . . ?
N1 Mn1 Cl2 106.20(7) . . ?
N3 Mn1 Cl2 101.85(6) . . ?
N2 Mn1 Cl2 159.89(6) . . ?
N1 Mn1 Cl3 94.94(6) . . ?
N3 Mn1 Cl3 96.71(6) . . ?
N2 Mn1 Cl3 95.28(6) . . ?
Cl2 Mn1 Cl3 104.72(3) . . ?
N1 Mn1 O1 80.40(8) . . ?
N3 Mn1 O1 80.13(8) . . ?
N2 Mn1 O1 69.89(7) . . ?
Cl2 Mn1 O1 90.14(5) . . ?
Cl3 Mn1 O1 165.15(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
N1 C1 C2 C3 -1.2(5) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C2 C3 C4 C5 0.9(6) . . . . ?
C3 C4 C5 N1 -1.1(5) . . . . ?
C3 C4 C5 C6 175.2(3) . . . . ?
N1 C5 C6 N2 -37.4(4) . . . . ?
C4 C5 C6 N2 146.0(3) . . . . ?
N2 C7 C8 N3 44.7(3) . . . . ?
N2 C7 C8 C9 -134.7(3) . . . . ?
N3 C8 C9 C10 -0.2(6) . . . . ?
C7 C8 C9 C10 179.2(4) . . . . ?
C8 C9 C10 C11 0.5(6) . . . . ?
C9 C10 C11 C12 -0.7(6) . . . . ?
C10 C11 C12 N3 0.6(6) . . . . ?
C18 C13 C14 C15 2.5(5) . . . . ?
N2 C13 C14 C15 -175.7(3) . . . . ?
C13 C14 C15 C16 -1.9(5) . . . . ?
C14 C15 C16 C17 0.3(5) . . . . ?
C15 C16 C17 C18 0.6(5) . . . . ?
C14 C13 C18 O1 178.9(3) . . . . ?
N2 C13 C18 O1 -2.8(4) . . . . ?
C14 C13 C18 C17 -1.6(4) . . . . ?
N2 C13 C18 C17 176.6(3) . . . . ?
C16 C17 C18 O1 179.5(3) . . . . ?
C16 C17 C18 C13 0.1(4) . . . . ?
C4 C5 N1 C1 0.1(4) . . . . ?
C6 C5 N1 C1 -176.4(3) . . . . ?
C4 C5 N1 Mn1 -178.7(2) . . . . ?
C6 C5 N1 Mn1 4.8(3) . . . . ?
C2 C1 N1 C5 1.0(4) . . . . ?
C2 C1 N1 Mn1 179.8(2) . . . . ?
C14 C13 N2 C6 -65.5(3) . . . . ?
C18 C13 N2 C6 116.2(3) . . . . ?
C14 C13 N2 C7 61.1(3) . . . . ?
C18 C13 N2 C7 -117.1(3) . . . . ?
C14 C13 N2 Mn1 175.3(2) . . . . ?
C18 C13 N2 Mn1 -3.0(3) . . . . ?
C5 C6 N2 C13 -78.7(3) . . . . ?
C5 C6 N2 C7 156.4(3) . . . . ?
C5 C6 N2 Mn1 47.2(3) . . . . ?
C8 C7 N2 C13 68.8(3) . . . . ?
C8 C7 N2 C6 -164.9(2) . . . . ?
C8 C7 N2 Mn1 -54.2(2) . . . . ?
C9 C8 N3 C12 0.1(5) . . . . ?
C7 C8 N3 C12 -179.4(3) . . . . ?
C9 C8 N3 Mn1 171.6(3) . . . . ?
C7 C8 N3 Mn1 -7.9(3) . . . . ?
C11 C12 N3 C8 -0.3(5) . . . . ?
C11 C12 N3 Mn1 -170.7(3) . . . . ?
C13 C18 O1 C19 -178.1(3) . . . . ?
C17 C18 O1 C19 2.5(4) . . . . ?
C13 C18 O1 Mn1 7.0(3) . . . . ?
C17 C18 O1 Mn1 -172.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O2 0.93 2.55 3.185(9) 126.1 . yes
C2 H2 O2 0.93 2.66 3.232(11) 120.4 . yes
C6 H6B Cl3 0.97 2.96 3.909(3) 166.0 3_556 yes
C7 H7B Cl3 0.97 2.89 3.518(3) 123.2 . yes
C11 H11 Cl2 0.93 2.77 3.609(4) 151.1 4_446 yes
C19 H19B Cl2 0.96 2.78 3.492(4) 132.1 . yes
C19 H19C Cl3 0.96 2.94 3.685(4) 134.9 2_554 yes
C1 H1 O2 0.93 2.55 3.185(9) 126.1 . yes
C2 H2 O2 0.93 2.66 3.232(11) 120.4 . yes
C6 H6B Cl3 0.97 2.96 3.909(3) 166.0 3_556 yes
C7 H7B Cl3 0.97 2.89 3.518(3) 123.2 . yes
C11 H11 Cl2 0.93 2.77 3.609(4) 151.1 4_446 yes
C19 H19B Cl2 0.96 2.78 3.492(4) 132.1 . yes
C19 H19C Cl3 0.96 2.94 3.685(4) 134.9 2_554 yes

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_BABU
_database_code_depnum_ccdc_archive 'CCDC 1527651'
loop_
_audit_author_name
_audit_author_address
'Anjana S'
;IIT Bombay
India
;
_audit_update_record             
;
2020-01-01 deposited with the CCDC.	2020-01-09 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         
'(C36 H34 N6 O4 Co2) . (Cl0.64 I1.36) . 0.36(C2 H3 N) . 4(H2 O)'
_chemical_formula_sum            'C36.73 H43.09 Cl0.64 Co2 I1.36 N6.36 O8'
_chemical_formula_weight         1015.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   16.0730(4)
_cell_length_b                   16.5200(4)
_cell_length_c                   16.8530(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4474.91(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9476
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      23.4

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             2036
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.772
_shelx_estimated_absorpt_T_min   0.619
_shelx_estimated_absorpt_T_max   0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_T_max  0.76
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18230
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.751
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4082
_reflns_number_gt                3125
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_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)+(0.1268P)²+5.0221P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         4082
_refine_ls_number_parameters     307
_refine_ls_number_restraints     104
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1988
_refine_ls_wR_factor_gt          0.1827
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.083
_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
C1 C 0.0509(4) 0.5688(4) -0.1748(4) 0.0504(15) Uani 1 1 d . . . . .
H1 H 0.023631 0.611065 -0.149307 0.061 Uiso 1 1 calc R U . . .
C2 C 0.0555(5) 0.5695(5) -0.2566(5) 0.070(2) Uani 1 1 d . . . . .
H2 H 0.029984 0.611355 -0.284367 0.084 Uiso 1 1 calc R U . . .
C3 C 0.0954(5) 0.5119(6) -0.2968(4) 0.075(3) Uani 1 1 d . . . . .
H3 H 0.098682 0.513007 -0.351916 0.090 Uiso 1 1 calc R U . . .
C4 C 0.1327(4) 0.4490(5) -0.2520(4) 0.0636(19) Uani 1 1 d . . . . .
H4 H 0.161062 0.406997 -0.276927 0.076 Uiso 1 1 calc R U . . .
C5 C 0.1257(3) 0.4517(4) -0.1688(3) 0.0436(13) Uani 1 1 d . . . . .
C6 C 0.1624(3) 0.3909(4) -0.1131(3) 0.0447(13) Uani 1 1 d . . . . .
H6A H 0.213984 0.369964 -0.134783 0.054 Uiso 1 1 calc R U . . .
H6B H 0.124212 0.346005 -0.106052 0.054 Uiso 1 1 calc R U . . .
C7 C 0.2550(3) 0.4798(3) -0.0379(3) 0.0362(12) Uani 1 1 d . . . . .
C8 C 0.3334(3) 0.4465(4) -0.0480(3) 0.0453(14) Uani 1 1 d . . . . .
H8 H 0.340260 0.390887 -0.053106 0.054 Uiso 1 1 calc R U . . .
C9 C 0.4008(4) 0.4975(4) -0.0503(4) 0.0557(18) Uani 1 1 d . . . . .
H9 H 0.453839 0.476316 -0.057931 0.067 Uiso 1 1 calc R U . . .
C10 C 0.3908(4) 0.5784(5) -0.0415(4) 0.0576(17) Uani 1 1 d . . . . .
H10 H 0.436914 0.612391 -0.043144 0.069 Uiso 1 1 calc R U . . .
C11 C 0.3124(3) 0.6105(4) -0.0301(3) 0.0506(15) Uani 1 1 d . . . . .
H11 H 0.306496 0.666143 -0.023680 0.061 Uiso 1 1 calc R U . . .
C12 C 0.2429(3) 0.5620(3) -0.0282(3) 0.0352(12) Uani 1 1 d . . . . .
C13 C 0.1791(3) 0.3749(3) 0.0351(3) 0.0412(13) Uani 1 1 d . . . . .
H13A H 0.231703 0.346302 0.037736 0.049 Uiso 1 1 calc R U . . .
H13B H 0.134828 0.335382 0.029768 0.049 Uiso 1 1 calc R U . . .
C14 C 0.1664(3) 0.4246(3) 0.1099(3) 0.0421(13) Uani 1 1 d . . . . .
C15 C 0.1964(4) 0.4068(4) 0.1853(4) 0.0581(17) Uani 1 1 d . . . . .
H15 H 0.227875 0.360282 0.192950 0.070 Uiso 1 1 calc R U . . .
C16 C 0.1801(5) 0.4576(5) 0.2498(4) 0.069(2) Uani 1 1 d . . . . .
H16 H 0.197908 0.444952 0.300832 0.082 Uiso 1 1 calc R U . . .
C17 C 0.1384(5) 0.5240(5) 0.2345(4) 0.067(2) Uani 1 1 d . . . . .
H17 H 0.127656 0.560294 0.275451 0.080 Uiso 1 1 calc R U . . .
C18 C 0.1098(3) 0.5414(4) 0.1587(3) 0.0448(13) Uani 1 1 d . . . . .
H18 H 0.081908 0.589946 0.150019 0.054 Uiso 1 1 calc R U . . .
N1 N 0.0839(2) 0.5101(3) -0.1311(3) 0.0377(11) Uani 1 1 d . . . . .
N2 N 0.1787(2) 0.4312(2) -0.0345(2) 0.0332(9) Uani 1 1 d . . . . .
N3 N 0.1212(3) 0.4905(3) 0.0971(3) 0.0354(10) Uani 1 1 d . . . . .
O1 O 0.00389(19) 0.4268(2) -0.0031(2) 0.0333(8) Uani 1 1 d D . . . .
O2 O 0.1659(2) 0.5900(2) -0.0187(2) 0.0387(8) Uani 1 1 d . . . . .
O3 O -0.0473(8) 0.750000 -0.1190(8) 0.143(4) Uani 1 2 d DS TU P . .
O4 O 0.2207(7) 0.750000 -0.2132(8) 0.132(4) Uani 1 2 d DS TU P . .
O5 O -0.0894(8) 0.750000 -0.2795(9) 0.157(5) Uani 1 2 d DS TU P . .
O6 O 0.1301(6) 0.750000 -0.0725(5) 0.092(2) Uani 1 2 d DS TU P . .
Co1 Co 0.08965(4) 0.50553(4) -0.01453(4) 0.0299(3) Uani 1 1 d . . . . .
I1 I 0.40090(6) 0.250000 0.08585(6) 0.0688(4) Uani 0.771(4) 2 d S T P . .
I2 I -0.02096(7) 0.250000 -0.11951(7) 0.0601(5) Uani 0.591(3) 2 d S T P . .
Cl1 Cl 0.2689(8) 0.250000 -0.3094(8) 0.115(4) Uani 0.637(6) 2 d S TU P A 1
N4 N 0.261(5) 0.250000 -0.304(4) 0.103(16) Uani 0.364(6) 2 d DS TU P B 2
C19 C 0.3019(18) 0.250000 -0.2474(17) 0.059(6) Uani 0.364(6) 2 d DS TU P B 2
C20 C 0.369(2) 0.250000 -0.193(2) 0.094(9) Uani 0.364(6) 2 d DS TU P B 2
H20A H 0.348153 0.250000 -0.139998 0.141 Uiso 0.364(6) 2 calc R U P B 2
H20B H 0.402564 0.202552 -0.201615 0.141 Uiso 0.182(3) 1 calc R U P B 2
H20C H 0.402564 0.297448 -0.201615 0.141 Uiso 0.182(3) 1 calc R U P B 2
H1A H -0.002(7) 0.3697(17) 0.004(7) 0.18(5) Uiso 1 1 d D . . . .
H3B H -0.052(8) 0.750000 -0.1727(18) 0.142(11) Uiso 1 2 d DS U P . .
H3A H 0.007(3) 0.750000 -0.105(7) 0.147(11) Uiso 1 2 d DS U P . .
H4A H 0.206(7) 0.750000 -0.1611(19) 0.128(11) Uiso 1 2 d DS U P . .
H4B H 0.175(4) 0.750000 -0.243(5) 0.130(11) Uiso 1 2 d DS U P . .
H5A H -0.044(4) 0.750000 -0.311(6) 0.158(12) Uiso 1 2 d DS U P . .
H5B H -0.136(4) 0.750000 -0.309(6) 0.155(12) Uiso 1 2 d DS U P . .
H6C H 0.132(5) 0.7947(6) -0.042(2) 0.093(11) Uiso 1 1 d D 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
C1 N1 1.328(7) . ?
C1 C2 1.380(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.333(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.418(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.408(9) . ?
C4 H4 0.9300 . ?
C5 N1 1.335(7) . ?
C5 C6 1.496(8) . ?
C6 N2 1.504(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C12 1.381(8) . ?
C7 C8 1.386(7) . ?
C7 N2 1.467(6) . ?
C8 C9 1.373(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.353(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(7) . ?
C11 H11 0.9300 . ?
C12 O2 1.332(6) . ?
C13 N2 1.497(6) . ?
C13 C14 1.518(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N3 1.327(7) . ?
C14 C15 1.389(8) . ?
C15 C16 1.398(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.311(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.388(9) . ?
C17 H17 0.9300 . ?
C18 N3 1.348(7) . ?
C18 H18 0.9300 . ?
N1 Co1 1.968(5) . ?
N2 Co1 1.916(4) . ?
N3 Co1 1.965(4) . ?
O1 Co1 1.897(3) 5_565 ?
O1 Co1 1.904(3) . ?
O1 H1A 0.96(2) . ?
O2 Co1 1.859(3) . ?
O3 H3B 0.91(2) . ?
O3 H3A 0.90(2) . ?
O4 H4A 0.91(2) . ?
O4 H4B 0.90(2) . ?
O5 H5A 0.90(2) . ?
O5 H5B 0.90(2) . ?
O6 H6C 0.897(19) . ?
O6 H6C 0.897(19) 8_575 ?
Co1 Co1 2.9287(12) 5_565 ?
N4 C19 1.164(17) . ?
C19 C20 1.415(17) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.6(7) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 121.8(7) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 117.1(7) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
C5 C4 C3 118.2(7) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
N1 C5 C4 122.5(6) . . ?
N1 C5 C6 112.7(5) . . ?
C4 C5 C6 124.8(6) . . ?
C5 C6 N2 108.9(5) . . ?
C5 C6 H6A 109.9 . . ?
N2 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
N2 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C12 C7 C8 122.1(5) . . ?
C12 C7 N2 114.6(4) . . ?
C8 C7 N2 123.3(5) . . ?
C9 C8 C7 118.6(6) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C10 C9 C8 120.6(6) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.2(6) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 121.3(6) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
O2 C12 C11 123.7(5) . . ?
O2 C12 C7 119.1(4) . . ?
C11 C12 C7 117.2(5) . . ?
N2 C13 C14 108.4(4) . . ?
N2 C13 H13A 110.0 . . ?
C14 C13 H13A 110.0 . . ?
N2 C13 H13B 110.0 . . ?
C14 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
N3 C14 C15 120.7(6) . . ?
N3 C14 C13 112.5(4) . . ?
C15 C14 C13 126.8(5) . . ?
C14 C15 C16 121.3(6) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 116.4(6) . . ?
C17 C16 H16 121.8 . . ?
C15 C16 H16 121.8 . . ?
C16 C17 C18 121.6(7) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
N3 C18 C17 122.3(6) . . ?
N3 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C1 N1 C5 117.7(5) . . ?
C1 N1 Co1 126.9(4) . . ?
C5 N1 Co1 115.0(4) . . ?
C7 N2 C13 111.5(4) . . ?
C7 N2 C6 110.7(4) . . ?
C13 N2 C6 114.6(4) . . ?
C7 N2 Co1 106.3(3) . . ?
C13 N2 Co1 105.3(3) . . ?
C6 N2 Co1 108.0(3) . . ?
C14 N3 C18 117.5(5) . . ?
C14 N3 Co1 113.6(4) . . ?
C18 N3 Co1 128.6(4) . . ?
Co1 O1 Co1 100.80(17) 5_565 . ?
Co1 O1 H1A 119(7) 5_565 . ?
Co1 O1 H1A 139(7) . . ?
C12 O2 Co1 110.8(3) . . ?
H3B O3 H3A 109(3) . . ?
H4A O4 H4B 109(3) . . ?
H5A O5 H5B 110(3) . . ?
H6C O6 H6C 111(4) . 8_575 ?
O2 Co1 O1 94.94(15) . 5_565 ?
O2 Co1 O1 173.51(16) . . ?
O1 Co1 O1 79.20(17) 5_565 . ?
O2 Co1 N2 89.00(17) . . ?
O1 Co1 N2 175.87(16) 5_565 . ?
O1 Co1 N2 96.93(17) . . ?
O2 Co1 N3 87.76(16) . . ?
O1 Co1 N3 97.40(17) 5_565 . ?
O1 Co1 N3 90.23(16) . . ?
N2 Co1 N3 83.97(18) . . ?
O2 Co1 N1 87.94(16) . . ?
O1 Co1 N1 95.55(17) 5_565 . ?
O1 Co1 N1 95.35(16) . . ?
N2 Co1 N1 83.33(18) . . ?
N3 Co1 N1 166.65(18) . . ?
O2 Co1 Co1 134.57(12) . 5_565 ?
O1 Co1 Co1 39.69(10) 5_565 5_565 ?
O1 Co1 Co1 39.50(10) . 5_565 ?
N2 Co1 Co1 136.42(13) . 5_565 ?
N3 Co1 Co1 94.94(13) . 5_565 ?
N1 Co1 Co1 97.08(12) . 5_565 ?
N4 C19 C20 165(5) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -1.7(10) . . . . ?
C1 C2 C3 C4 0.5(10) . . . . ?
C2 C3 C4 C5 -0.4(9) . . . . ?
C3 C4 C5 N1 1.5(9) . . . . ?
C3 C4 C5 C6 -179.1(5) . . . . ?
N1 C5 C6 N2 -27.5(6) . . . . ?
C4 C5 C6 N2 153.0(5) . . . . ?
C12 C7 C8 C9 -1.6(8) . . . . ?
N2 C7 C8 C9 180.0(5) . . . . ?
C7 C8 C9 C10 1.1(10) . . . . ?
C8 C9 C10 C11 0.0(11) . . . . ?
C9 C10 C11 C12 -0.6(10) . . . . ?
C10 C11 C12 O2 -178.9(5) . . . . ?
C10 C11 C12 C7 0.2(8) . . . . ?
C8 C7 C12 O2 -180.0(5) . . . . ?
N2 C7 C12 O2 -1.4(7) . . . . ?
C8 C7 C12 C11 1.0(8) . . . . ?
N2 C7 C12 C11 179.5(4) . . . . ?
N2 C13 C14 N3 30.0(6) . . . . ?
N2 C13 C14 C15 -150.3(5) . . . . ?
N3 C14 C15 C16 -0.1(9) . . . . ?
C13 C14 C15 C16 -179.8(6) . . . . ?
C14 C15 C16 C17 -2.8(10) . . . . ?
C15 C16 C17 C18 1.9(11) . . . . ?
C16 C17 C18 N3 1.9(10) . . . . ?
C2 C1 N1 C5 2.6(8) . . . . ?
C2 C1 N1 Co1 174.9(5) . . . . ?
C4 C5 N1 C1 -2.5(8) . . . . ?
C6 C5 N1 C1 177.9(5) . . . . ?
C4 C5 N1 Co1 -175.7(4) . . . . ?
C6 C5 N1 Co1 4.7(6) . . . . ?
C12 C7 N2 C13 -115.6(5) . . . . ?
C8 C7 N2 C13 62.9(6) . . . . ?
C12 C7 N2 C6 115.6(5) . . . . ?
C8 C7 N2 C6 -65.9(6) . . . . ?
C12 C7 N2 Co1 -1.4(5) . . . . ?
C8 C7 N2 Co1 177.1(4) . . . . ?
C14 C13 N2 C7 72.4(5) . . . . ?
C14 C13 N2 C6 -160.9(4) . . . . ?
C14 C13 N2 Co1 -42.4(4) . . . . ?
C5 C6 N2 C7 -78.5(5) . . . . ?
C5 C6 N2 C13 154.3(4) . . . . ?
C5 C6 N2 Co1 37.4(5) . . . . ?
C15 C14 N3 C18 3.7(7) . . . . ?
C13 C14 N3 C18 -176.5(4) . . . . ?
C15 C14 N3 Co1 177.6(4) . . . . ?
C13 C14 N3 Co1 -2.6(5) . . . . ?
C17 C18 N3 C14 -4.7(8) . . . . ?
C17 C18 N3 Co1 -177.5(4) . . . . ?
C11 C12 O2 Co1 -177.3(4) . . . . ?
C7 C12 O2 Co1 3.7(6) . . . . ?
C12 O2 Co1 O1 177.7(3) . . . 5_565 ?
C12 O2 Co1 N2 -3.6(3) . . . . ?
C12 O2 Co1 N3 80.4(3) . . . . ?
C12 O2 Co1 N1 -86.9(3) . . . . ?
C12 O2 Co1 Co1 175.1(2) . . . 5_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O3 0.93 2.61 3.513(9) 162.9 . yes
C6 H6B I2 0.97 2.83 3.757(6) 160.1 . yes
C13 H13A I1 0.97 3.25 4.207(5) 168.1 . yes
C13 H13B O3 0.97 2.50 3.278(10) 137.6 5_565 yes
C15 H15 O4 0.93 2.55 3.379(9) 148.6 2_565 yes
C18 H18 I2 0.93 2.87 3.788(6) 171.1 5_565 yes
O1 H1A I2 0.96(2) 2.89(10) 3.542(4) 126(9) . yes
O3 H3B O5 0.91(2) 1.90(4) 2.79(2) 166(13) . yes
O3 H3A O6 0.90(2) 2.06(3) 2.958(18) 179(12) . yes
O4 H4A O6 0.91(2) 1.92(6) 2.783(14) 156(10) . yes
O4 H4B I1 0.90(2) 3.12(6) 3.909(15) 147(9) 2_564 yes
O5 H5A I1 0.90(2) 2.89(2) 3.785(12) 179(10) 2_564 yes
O5 H5B O4 0.90(2) 2.34(8) 3.055(16) 137(10) 6 yes
O6 H6C O2 0.897(19) 2.02(2) 2.852(5) 153(5) 8_575 yes
C1 H1 O3 0.93 2.61 3.513(9) 162.9 . yes
C6 H6B I2 0.97 2.83 3.757(6) 160.1 . yes
C13 H13A I1 0.97 3.25 4.207(5) 168.1 . yes
C13 H13B O3 0.97 2.50 3.278(10) 137.6 5_565 yes
C15 H15 O4 0.93 2.55 3.379(9) 148.6 2_565 yes
C18 H18 I2 0.93 2.87 3.788(6) 171.1 5_565 yes
O1 H1A I2 0.96(2) 2.89(10) 3.542(4) 126(9) . yes
O3 H3B O5 0.91(2) 1.90(4) 2.79(2) 166(13) . yes
O3 H3A O6 0.90(2) 2.06(3) 2.958(18) 179(12) . yes
O4 H4A O6 0.91(2) 1.92(6) 2.783(14) 156(10) . yes
O4 H4B I1 0.90(2) 3.12(6) 3.909(15) 147(9) 2_564 yes
O5 H5A I1 0.90(2) 2.89(2) 3.785(12) 179(10) 2_564 yes
O5 H5B O4 0.90(2) 2.34(8) 3.055(16) 137(10) 6 yes
O6 H6C O2 0.897(19) 2.02(2) 2.852(5) 153(5) 8_575 yes

_refine_diff_density_max         1.828
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.176

# start Validation Reply Form
_vrf_PLAT094_BABU                
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.57 Report
RESPONSE: There is still more disordered components for lattice 
acetonitrile. But attempts to model the same did not succeed.
;
_vrf_PLAT420_BABU                
;
PROBLEM: D-H Without Acceptor       O4       --H4B      .     Please Check 
RESPONSE: There is a short contact interaction of H4B with I1. However,
no acceptor type atom is found in the hydrogen bonding interaction 
vicinity. 
;
# end Validation Reply Form

####################################################################### 
# 
# 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_ANJANA
_database_code_depnum_ccdc_archive 'CCDC 1919763'
loop_
_audit_author_name
_audit_author_address
'Anjana S'
;IIT Bombay
India
;
_audit_update_record             
;
2019-05-30 deposited with the CCDC.	2020-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H25 Cl2 Co N3 O12'
_chemical_formula_weight         617.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   10.8936(5)
_cell_length_b                   19.2866(10)
_cell_length_c                   13.2468(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.981(2)
_cell_angle_gamma                90
_cell_volume                     2562.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6788
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      24.6

_exptl_crystal_description       block
_exptl_crystal_colour            'pale pink'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             1268
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.944
_shelx_estimated_absorpt_T_min   0.733
_shelx_estimated_absorpt_T_max   0.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31784
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.112
_diffrn_reflns_theta_max         25.129
_diffrn_reflns_theta_full        25.129
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4555
_reflns_number_gt                3409
_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       'APEXII (Bruker, 2012)'
_computing_cell_refinement       'APEXII/SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2012)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'

_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)+(0.0575P)²+2.3025P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         4555
_refine_ls_number_parameters     430
_refine_ls_number_restraints     582
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.180
_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
C1 C 0.7357(4) 0.0895(2) 0.4867(3) 0.0551(9) Uani 1 1 d . . . . .
H1 H 0.826272 0.080456 0.508248 0.066 Uiso 1 1 calc R U . . .
C2 C 0.6461(5) 0.0469(2) 0.4115(3) 0.0694(12) Uani 1 1 d . . . . .
H2 H 0.674703 0.009383 0.382160 0.083 Uiso 1 1 calc R U . . .
C3 C 0.5139(5) 0.0605(3) 0.3805(4) 0.0882(15) Uani 1 1 d . . . . .
H3 H 0.450944 0.032490 0.328790 0.106 Uiso 1 1 calc R U . . .
C4 C 0.4730(4) 0.1156(2) 0.4254(4) 0.0716(12) Uani 1 1 d . . . . .
H4 H 0.382852 0.125091 0.405208 0.086 Uiso 1 1 calc R U . . .
C5 C 0.5681(3) 0.15616(18) 0.5005(3) 0.0450(8) Uani 1 1 d . . . . .
C6 C 0.5336(3) 0.21790(19) 0.5538(3) 0.0471(8) Uani 1 1 d . . . . .
H6A H 0.541520 0.260010 0.516753 0.057 Uiso 1 1 calc R U . . .
H6B H 0.442192 0.214112 0.547733 0.057 Uiso 1 1 calc R U . . .
C7 C 0.5864(3) 0.17179(17) 0.7367(3) 0.0406(7) Uani 1 1 d . . . . .
C8 C 0.4726(4) 0.1812(2) 0.7575(3) 0.0562(10) Uani 1 1 d . . . . .
H8 H 0.417914 0.219267 0.728055 0.067 Uiso 1 1 calc R U . . .
C9 C 0.4398(4) 0.1344(2) 0.8215(4) 0.0638(11) Uani 1 1 d . . . . .
H9 H 0.364209 0.141626 0.836422 0.077 Uiso 1 1 calc R U . . .
C10 C 0.5179(4) 0.0776(2) 0.8631(3) 0.0608(10) Uani 1 1 d . . . . .
H10 H 0.495061 0.045938 0.905811 0.073 Uiso 1 1 calc R U . . .
C11 C 0.6310(4) 0.06701(18) 0.8417(3) 0.0509(9) Uani 1 1 d . . . . .
H11 H 0.683942 0.028152 0.869713 0.061 Uiso 1 1 calc R U . . .
C12 C 0.6650(3) 0.11379(16) 0.7792(3) 0.0403(7) Uani 1 1 d . . . . .
C18 C 0.8891(4) 0.3416(2) 0.6105(3) 0.0547(9) Uani 1 1 d . . . . .
H18 H 0.951515 0.318937 0.590444 0.066 Uiso 1 1 calc R U . . .
C17 C 0.8821(4) 0.4123(2) 0.6049(3) 0.0651(11) Uani 1 1 d . . . . .
H17 H 0.940519 0.437313 0.583051 0.078 Uiso 1 1 calc R U . . .
C16 C 0.7886(4) 0.4461(2) 0.6317(4) 0.0683(11) Uani 1 1 d . . . . .
H16 H 0.782416 0.494237 0.627878 0.082 Uiso 1 1 calc R U . . .
C15 C 0.7043(4) 0.40823(19) 0.6643(3) 0.0576(10) Uani 1 1 d . . . . .
H15 H 0.638889 0.430148 0.681446 0.069 Uiso 1 1 calc R U . . .
C14 C 0.7179(3) 0.33659(18) 0.6714(3) 0.0458(8) Uani 1 1 d . . . . .
C13 C 0.6344(4) 0.29320(17) 0.7141(3) 0.0480(8) Uani 1 1 d . . . . .
H13A H 0.674057 0.292686 0.793603 0.058 Uiso 1 1 calc R U . . .
H13B H 0.545802 0.312977 0.691021 0.058 Uiso 1 1 calc R U . . .
C19 C 0.8577(4) 0.0464(2) 0.7897(4) 0.0688(11) Uani 1 1 d . . . . .
H19A H 0.894241 0.043745 0.868299 0.103 Uiso 1 1 calc R U . . .
H19B H 0.928962 0.048506 0.764269 0.103 Uiso 1 1 calc R U . . .
H19C H 0.804219 0.006032 0.759739 0.103 Uiso 1 1 calc R U . . .
N1 N 0.6983(3) 0.14404(15) 0.5307(2) 0.0447(7) Uani 1 1 d . . . . .
N2 N 0.6254(2) 0.22129(14) 0.6716(2) 0.0387(6) Uani 1 1 d . . . . .
N3 N 0.8083(3) 0.30352(15) 0.6441(2) 0.0460(7) Uani 1 1 d . . . . .
O1 O 0.7768(2) 0.10721(12) 0.7551(2) 0.0501(6) Uani 1 1 d . . . . .
O2 O 0.9290(3) 0.22316(15) 0.8432(2) 0.0598(7) Uani 1 1 d D . . . .
O3 O 0.9976(3) 0.17208(18) 0.6688(3) 0.0702(8) Uani 1 1 d D . . . .
Co1 Co 0.81974(4) 0.19673(2) 0.67421(4) 0.04121(16) Uani 1 1 d . . . . .
Cl1 Cl 0.09386(11) 0.10691(5) 0.44909(9) 0.0666(3) Uani 1 1 d D U . . .
O4 O -0.0355(7) 0.1363(5) 0.3960(7) 0.089(2) Uani 0.645(9) 1 d D U P A 1
O5 O 0.1155(10) 0.0537(4) 0.3923(5) 0.129(3) Uani 0.645(9) 1 d D U P A 1
O6 O 0.1075(6) 0.0845(3) 0.5558(4) 0.0846(19) Uani 0.645(9) 1 d D U P A 1
O7 O 0.1895(6) 0.1614(4) 0.4640(7) 0.122(3) Uani 0.645(9) 1 d D U P A 1
O4' O -0.0154(13) 0.1495(10) 0.4435(12) 0.089(4) Uani 0.355(9) 1 d D U P A 2
O5' O 0.0407(13) 0.0385(5) 0.4120(11) 0.110(4) Uani 0.355(9) 1 d D U P A 2
O6' O 0.1413(13) 0.1293(7) 0.3694(11) 0.124(4) Uani 0.355(9) 1 d D U P A 2
O7' O 0.1921(16) 0.1076(8) 0.5519(9) 0.159(6) Uani 0.355(9) 1 d D U P A 2
Cl2 Cl 0.23708(9) 0.37078(5) 0.54791(8) 0.0540(2) Uani 1 1 d D U . . .
O8 O 0.1213(6) 0.4004(5) 0.4794(8) 0.150(3) Uani 0.674(7) 1 d D U P B 1
O9 O 0.2478(8) 0.3804(4) 0.6582(4) 0.116(2) Uani 0.674(7) 1 d D U P B 1
O10 O 0.2268(9) 0.2990(3) 0.5329(8) 0.144(3) Uani 0.674(7) 1 d D U P B 1
O11 O 0.3466(8) 0.3962(6) 0.5353(9) 0.121(3) Uani 0.674(7) 1 d D U P B 1
O8' O 0.1609(11) 0.4238(6) 0.5603(13) 0.103(4) Uani 0.326(7) 1 d D U P B 2
O9' O 0.2748(15) 0.3198(8) 0.6188(14) 0.145(6) Uani 0.326(7) 1 d D U P B 2
O10' O 0.1783(13) 0.3497(8) 0.4370(9) 0.124(5) Uani 0.326(7) 1 d D U P B 2
O11' O 0.3585(14) 0.4064(9) 0.5526(16) 0.098(6) Uani 0.326(7) 1 d D U P B 2
O12 O 0.1964(4) 0.2580(2) 0.7745(3) 0.0879(10) Uani 1 1 d D . . . .
H2A H 0.991(4) 0.1971(18) 0.883(4) 0.102(13) Uiso 1 1 d D . . . .
H2B H 0.944(5) 0.2642(11) 0.865(4) 0.102(13) Uiso 1 1 d D . . . .
H3A H 1.060(4) 0.200(2) 0.700(4) 0.105(13) Uiso 1 1 d D . . . .
H3B H 1.013(5) 0.146(2) 0.625(4) 0.105(13) Uiso 1 1 d D . . . .
H12A H 0.208(8) 0.290(3) 0.736(5) 0.16(2) Uiso 1 1 d D . . . .
H12B H 0.186(7) 0.275(3) 0.829(4) 0.16(2) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.340(5) . ?
C1 C2 1.366(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.361(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(5) . ?
C4 H4 0.9300 . ?
C5 N1 1.336(4) . ?
C5 C6 1.505(5) . ?
C6 N2 1.491(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.382(5) . ?
C7 C12 1.388(4) . ?
C7 N2 1.457(4) . ?
C8 C9 1.376(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(5) . ?
C11 H11 0.9300 . ?
C12 O1 1.380(4) . ?
C18 N3 1.348(4) . ?
C18 C17 1.368(6) . ?
C18 H18 0.9300 . ?
C17 C16 1.368(6) . ?
C17 H17 0.9300 . ?
C16 C15 1.369(6) . ?
C16 H16 0.9300 . ?
C15 C14 1.389(5) . ?
C15 H15 0.9300 . ?
C14 N3 1.336(4) . ?
C14 C13 1.499(5) . ?
C13 N2 1.485(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C19 O1 1.431(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N1 Co1 2.106(3) . ?
N2 Co1 2.157(3) . ?
N3 Co1 2.092(3) . ?
O1 Co1 2.177(2) . ?
O2 Co1 2.146(3) . ?
O2 H2A 0.840(19) . ?
O2 H2B 0.838(19) . ?
O3 Co1 2.023(3) . ?
O3 H3A 0.843(19) . ?
O3 H3B 0.836(19) . ?
Cl1 O5 1.346(5) . ?
Cl1 O7' 1.364(9) . ?
Cl1 O6' 1.413(8) . ?
Cl1 O4' 1.424(9) . ?
Cl1 O4 1.425(6) . ?
Cl1 O6 1.429(5) . ?
Cl1 O7 1.438(5) . ?
Cl1 O5' 1.447(9) . ?
Cl2 O9' 1.310(9) . ?
Cl2 O8 1.359(5) . ?
Cl2 O11 1.359(6) . ?
Cl2 O8' 1.366(8) . ?
Cl2 O10 1.396(6) . ?
Cl2 O10' 1.414(9) . ?
Cl2 O9 1.431(5) . ?
Cl2 O11' 1.471(11) . ?
O12 H12A 0.84(2) . ?
O12 H12B 0.84(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.5(4) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 118.3(4) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 120.2(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 118.4(4) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 122.1(3) . . ?
N1 C5 C6 115.4(3) . . ?
C4 C5 C6 122.5(3) . . ?
N2 C6 C5 109.7(3) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C12 119.0(3) . . ?
C8 C7 N2 121.6(3) . . ?
C12 C7 N2 119.4(3) . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 O1 123.4(3) . . ?
C11 C12 C7 120.4(3) . . ?
O1 C12 C7 116.2(3) . . ?
N3 C18 C17 122.1(4) . . ?
N3 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C16 C17 C18 119.5(4) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C16 C15 119.1(4) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C15 C14 119.1(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
N3 C14 C15 121.8(3) . . ?
N3 C14 C13 117.1(3) . . ?
C15 C14 C13 121.1(3) . . ?
N2 C13 C14 109.8(3) . . ?
N2 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
N2 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C5 N1 C1 118.4(3) . . ?
C5 N1 Co1 113.9(2) . . ?
C1 N1 Co1 125.5(2) . . ?
C7 N2 C13 112.3(2) . . ?
C7 N2 C6 111.1(3) . . ?
C13 N2 C6 110.8(3) . . ?
C7 N2 Co1 111.00(19) . . ?
C13 N2 Co1 106.23(19) . . ?
C6 N2 Co1 105.07(18) . . ?
C14 N3 C18 118.4(3) . . ?
C14 N3 Co1 114.5(2) . . ?
C18 N3 Co1 126.9(2) . . ?
C12 O1 C19 119.3(3) . . ?
C12 O1 Co1 114.81(18) . . ?
C19 O1 Co1 125.8(2) . . ?
Co1 O2 H2A 120(3) . . ?
Co1 O2 H2B 123(3) . . ?
H2A O2 H2B 110(3) . . ?
Co1 O3 H3A 116(3) . . ?
Co1 O3 H3B 128(3) . . ?
H3A O3 H3B 113(3) . . ?
O3 Co1 N3 102.21(13) . . ?
O3 Co1 N1 97.33(11) . . ?
N3 Co1 N1 109.47(11) . . ?
O3 Co1 O2 86.76(12) . . ?
N3 Co1 O2 86.12(11) . . ?
N1 Co1 O2 162.45(11) . . ?
O3 Co1 N2 177.16(11) . . ?
N3 Co1 N2 78.20(10) . . ?
N1 Co1 N2 79.91(10) . . ?
O2 Co1 N2 96.08(11) . . ?
O3 Co1 O1 102.92(12) . . ?
N3 Co1 O1 150.02(10) . . ?
N1 Co1 O1 83.20(10) . . ?
O2 Co1 O1 79.25(11) . . ?
N2 Co1 O1 77.51(9) . . ?
O7' Cl1 O6' 111.7(8) . . ?
O7' Cl1 O4' 111.1(8) . . ?
O6' Cl1 O4' 109.1(8) . . ?
O5 Cl1 O4 112.5(5) . . ?
O5 Cl1 O6 110.4(4) . . ?
O4 Cl1 O6 108.0(4) . . ?
O5 Cl1 O7 111.0(5) . . ?
O4 Cl1 O7 107.5(5) . . ?
O6 Cl1 O7 107.2(4) . . ?
O7' Cl1 O5' 113.7(8) . . ?
O6' Cl1 O5' 103.9(7) . . ?
O4' Cl1 O5' 107.0(9) . . ?
O8 Cl2 O11 113.4(6) . . ?
O9' Cl2 O8' 120.7(9) . . ?
O8 Cl2 O10 108.6(5) . . ?
O11 Cl2 O10 111.4(6) . . ?
O9' Cl2 O10' 114.7(9) . . ?
O8' Cl2 O10' 106.9(7) . . ?
O8 Cl2 O9 108.1(5) . . ?
O11 Cl2 O9 110.7(5) . . ?
O10 Cl2 O9 104.2(4) . . ?
O9' Cl2 O11' 107.2(8) . . ?
O8' Cl2 O11' 102.9(7) . . ?
O10' Cl2 O11' 102.3(8) . . ?
H12A O12 H12B 111(3) . . ?

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
N1 C1 C2 C3 0.0(7) . . . . ?
C1 C2 C3 C4 -0.7(8) . . . . ?
C2 C3 C4 C5 0.6(8) . . . . ?
C3 C4 C5 N1 0.4(7) . . . . ?
C3 C4 C5 C6 179.6(4) . . . . ?
N1 C5 C6 N2 -40.1(4) . . . . ?
C4 C5 C6 N2 140.6(4) . . . . ?
C12 C7 C8 C9 1.5(6) . . . . ?
N2 C7 C8 C9 -178.4(4) . . . . ?
C7 C8 C9 C10 -1.4(6) . . . . ?
C8 C9 C10 C11 0.5(6) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C11 C12 O1 179.4(3) . . . . ?
C10 C11 C12 C7 -0.2(5) . . . . ?
C8 C7 C12 C11 -0.7(5) . . . . ?
N2 C7 C12 C11 179.2(3) . . . . ?
C8 C7 C12 O1 179.6(3) . . . . ?
N2 C7 C12 O1 -0.5(4) . . . . ?
N3 C18 C17 C16 -1.5(6) . . . . ?
C18 C17 C16 C15 0.4(6) . . . . ?
C17 C16 C15 C14 1.3(6) . . . . ?
C16 C15 C14 N3 -2.0(6) . . . . ?
C16 C15 C14 C13 175.7(4) . . . . ?
N3 C14 C13 N2 -25.7(4) . . . . ?
C15 C14 C13 N2 156.5(3) . . . . ?
C4 C5 N1 C1 -1.1(5) . . . . ?
C6 C5 N1 C1 179.6(3) . . . . ?
C4 C5 N1 Co1 -165.0(3) . . . . ?
C6 C5 N1 Co1 15.7(4) . . . . ?
C2 C1 N1 C5 1.0(6) . . . . ?
C2 C1 N1 Co1 162.8(3) . . . . ?
C8 C7 N2 C13 53.9(4) . . . . ?
C12 C7 N2 C13 -126.0(3) . . . . ?
C8 C7 N2 C6 -70.8(4) . . . . ?
C12 C7 N2 C6 109.3(3) . . . . ?
C8 C7 N2 Co1 172.7(3) . . . . ?
C12 C7 N2 Co1 -7.2(4) . . . . ?
C14 C13 N2 C7 160.5(3) . . . . ?
C14 C13 N2 C6 -74.6(3) . . . . ?
C14 C13 N2 Co1 39.0(3) . . . . ?
C5 C6 N2 C7 -78.3(3) . . . . ?
C5 C6 N2 C13 156.2(3) . . . . ?
C5 C6 N2 Co1 41.8(3) . . . . ?
C15 C14 N3 C18 1.0(5) . . . . ?
C13 C14 N3 C18 -176.9(3) . . . . ?
C15 C14 N3 Co1 175.2(3) . . . . ?
C13 C14 N3 Co1 -2.7(4) . . . . ?
C17 C18 N3 C14 0.8(5) . . . . ?
C17 C18 N3 Co1 -172.6(3) . . . . ?
C11 C12 O1 C19 4.6(5) . . . . ?
C7 C12 O1 C19 -175.7(3) . . . . ?
C11 C12 O1 Co1 -171.7(3) . . . . ?
C7 C12 O1 Co1 8.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O4'^b 0.93 2.58 3.199(17) 124.6 1_655 yes
C2 H2 O7'^b 0.93 2.64 3.398(15) 139.1 3_656 yes
C4 H4 O7^a 0.93 2.61 3.437(8) 148.4 . yes
C4 H4 O6'^b 0.93 2.49 3.403(13) 169.0 . yes
C8 H8 O9'^b 0.93 2.55 3.475(12) 170.6 . yes
C11 H11 O8'^b 0.93 2.56 3.487(11) 176.1 2_646 yes
C17 H17 O8'^b 0.93 2.55 3.320(11) 140.8 1_655 yes
C19 H19A O8^a 0.96 2.57 3.159(7) 119.9 4_666 yes
C19 H19A O8'^b 0.96 2.66 3.145(10) 112.1 2_646 yes
O2 H2A O8^a 0.840(19) 2.40(2) 3.220(11) 165(4) 4_666 yes
O2 H2A O10^a 0.840(19) 2.56(4) 3.264(10) 142(4) 4_666 yes
O2 H2A O10'^b 0.840(19) 2.09(3) 2.874(11) 155(5) 4_666 yes
O3 H3B Cl1 0.836(19) 2.89(3) 3.680(3) 158(4) 1_655 yes
O3 H3B O6^a 0.836(19) 2.01(3) 2.816(6) 162(5) 1_655 yes
O3 H3B O4'^b 0.836(19) 2.30(4) 2.965(14) 137(5) 1_655 yes
O3 H3B O7'^b 0.836(19) 2.60(4) 3.317(19) 144(4) 1_655 yes
O2 H2B Cl1 0.838(19) 2.94(3) 3.737(3) 159(4) 4_666 yes
O2 H2B O4^a 0.838(19) 1.96(2) 2.787(10) 172(5) 4_666 yes
O2 H2B O4'^b 0.838(19) 1.92(3) 2.744(18) 169(5) 4_666 yes
O3 H3A O12 0.843(19) 1.81(2) 2.651(5) 176(6) 1_655 yes
O12 H12A O9^a 0.84(2) 2.16(3) 2.991(8) 171(7) . yes
O12 H12A O9'^b 0.84(2) 2.04(4) 2.790(14) 149(6) . yes
O12 H12B O7^a 0.84(2) 2.16(3) 2.978(9) 165(6) 4_566 yes
O12 H12B O6'^b 0.84(2) 2.04(6) 2.693(11) 134(6) 4_566 yes

_refine_diff_density_max         0.585
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 1920584'
loop_
_audit_author_name
_audit_author_address
'Anjana S'
;IIT Bombay
India
;
_audit_update_record             
;
2019-06-04 deposited with the CCDC.	2020-01-09 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 H21 Cl Co I N3 O6'
_chemical_formula_weight         608.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.0682(3)
_cell_length_b                   11.6181(4)
_cell_length_c                   12.1412(4)
_cell_angle_alpha                103.0870(10)
_cell_angle_beta                 104.1930(10)
_cell_angle_gamma                90.1940(10)
_cell_volume                     1205.53(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.1

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_F_000             602
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.141
_shelx_estimated_absorpt_T_min   0.586
_shelx_estimated_absorpt_T_max   0.783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_T_max  0.72
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker kappa apex2 CCD Diffrctometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17827
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.803
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4420
_reflns_number_gt                3890
_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       'APEXII (Bruker, 2012)'
_computing_cell_refinement       'APEXII/SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_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)+(0.0431P)²+1.7765P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         4420
_refine_ls_number_parameters     327
_refine_ls_number_restraints     218
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3577(4) 0.0367(3) 0.3757(3) 0.0413(8) Uani 1 1 d . . . . .
H1 H 0.456157 0.055713 0.372760 0.050 Uiso 1 1 calc R U . . .
C2 C 0.3230(5) -0.0755(3) 0.3856(3) 0.0515(10) Uani 1 1 d . . . . .
H2 H 0.396910 -0.130720 0.390556 0.062 Uiso 1 1 calc R U . . .
C3 C 0.1777(5) -0.1039(4) 0.3880(3) 0.0558(10) Uani 1 1 d . . . . .
H3 H 0.151561 -0.178930 0.395008 0.067 Uiso 1 1 calc R U . . .
C4 C 0.0706(5) -0.0212(4) 0.3799(3) 0.0504(10) Uani 1 1 d . . . . .
H4 H -0.029364 -0.040207 0.379374 0.060 Uiso 1 1 calc R U . . .
C5 C 0.1127(4) 0.0912(3) 0.3726(3) 0.0371(7) Uani 1 1 d . . . . .
C6 C 0.0055(4) 0.1887(3) 0.3711(3) 0.0431(8) Uani 1 1 d . . . . .
H6A H -0.098753 0.155338 0.340796 0.052 Uiso 1 1 calc R U . . .
H6B H 0.016264 0.235462 0.450067 0.052 Uiso 1 1 calc R U . . .
C7 C -0.0120(4) 0.3866(3) 0.3251(4) 0.0501(9) Uani 1 1 d . . . . .
H7A H 0.009836 0.416152 0.409210 0.060 Uiso 1 1 calc R U . . .
H7B H -0.121063 0.386316 0.292960 0.060 Uiso 1 1 calc R U . . .
C8 C 0.0708(4) 0.4642(3) 0.2736(4) 0.0489(9) Uani 1 1 d . . . . .
C9 C 0.0006(6) 0.5473(4) 0.2179(5) 0.0768(15) Uani 1 1 d . . . . .
H9 H -0.102690 0.557957 0.210277 0.092 Uiso 1 1 calc R U . . .
C10 C 0.0860(7) 0.6141(5) 0.1737(6) 0.0927(19) Uani 1 1 d . . . . .
H10 H 0.040268 0.670626 0.135379 0.111 Uiso 1 1 calc R U . . .
C11 C 0.2371(6) 0.5984(4) 0.1857(5) 0.0769(15) Uani 1 1 d . . . . .
H11 H 0.295764 0.644034 0.156549 0.092 Uiso 1 1 calc R U . . .
C12 C 0.3012(5) 0.5132(4) 0.2418(4) 0.0570(10) Uani 1 1 d . . . . .
H12 H 0.404446 0.501838 0.250088 0.068 Uiso 1 1 calc R U . . .
C13 C -0.0183(4) 0.2111(3) 0.1718(3) 0.0389(8) Uani 1 1 d . . . . .
C14 C -0.1735(5) 0.1898(4) 0.1233(4) 0.0561(10) Uani 1 1 d . . . . .
H14 H -0.240634 0.205903 0.170967 0.067 Uiso 1 1 calc R U . . .
C15 C -0.2293(6) 0.1445(4) 0.0045(4) 0.0688(13) Uani 1 1 d . . . . .
H15 H -0.333618 0.130367 -0.028210 0.083 Uiso 1 1 calc R U . . .
C16 C -0.1288(6) 0.1207(4) -0.0646(4) 0.0657(13) Uani 1 1 d . . . . .
H16 H -0.166250 0.091050 -0.144651 0.079 Uiso 1 1 calc R U . . .
C17 C 0.0250(5) 0.1395(3) -0.0186(3) 0.0506(10) Uani 1 1 d . . . . .
H17 H 0.091187 0.121998 -0.066921 0.061 Uiso 1 1 calc R U . . .
C18 C 0.0822(4) 0.1850(3) 0.1008(3) 0.0370(7) Uani 1 1 d . . . . .
C19 C 0.3392(6) 0.1955(6) 0.0815(4) 0.0890(19) Uani 1 1 d . . . . .
H19A H 0.327599 0.117210 0.031840 0.134 Uiso 1 1 calc R U . . .
H19B H 0.441786 0.210312 0.129498 0.134 Uiso 1 1 calc R U . . .
H19C H 0.318087 0.252440 0.034312 0.134 Uiso 1 1 calc R U . . .
Co1 Co 0.28609(5) 0.29100(4) 0.34392(4) 0.03316(12) Uani 1 1 d . . . . .
I1 I 0.59303(3) 0.31830(2) 0.39396(2) 0.05149(11) Uani 1 1 d . . . . .
N1 N 0.2557(3) 0.1195(2) 0.3701(2) 0.0342(6) Uani 1 1 d . . . . .
N2 N 0.0395(3) 0.2651(2) 0.2967(2) 0.0357(6) Uani 1 1 d . . . . .
N3 N 0.2200(3) 0.4465(3) 0.2848(3) 0.0423(7) Uani 1 1 d . . . . .
O1 O 0.2353(3) 0.2052(2) 0.15437(19) 0.0420(6) Uani 1 1 d . . . . .
O2 O 0.2783(3) 0.3755(3) 0.5175(2) 0.0513(6) Uani 1 1 d D . . . .
Cl1 Cl 0.33428(14) 0.21122(15) 0.75379(10) 0.0749(4) Uani 1 1 d . U . . .
O3 O 0.2062(7) 0.2217(7) 0.7952(7) 0.091(2) Uani 0.609(7) 1 d . U P A 1
O4 O 0.3009(14) 0.1624(13) 0.6388(7) 0.164(4) Uani 0.609(7) 1 d . U P A 1
O5 O 0.3915(16) 0.3299(15) 0.7633(16) 0.211(5) Uani 0.609(7) 1 d . U P A 1
O6 O 0.4548(10) 0.1757(13) 0.8240(8) 0.146(4) Uani 0.609(7) 1 d . U P A 1
O6' O 0.344(2) 0.0910(15) 0.7588(16) 0.147(5) Uani 0.391(7) 1 d . U P A 2
O3' O 0.1895(19) 0.2303(15) 0.694(2) 0.160(6) Uani 0.391(7) 1 d . U P A 2
O4' O 0.4052(17) 0.2478(16) 0.6750(13) 0.110(4) Uani 0.391(7) 1 d . U P A 2
O5' O 0.379(3) 0.296(2) 0.8548(16) 0.185(6) Uani 0.391(7) 1 d . U P A 2
H2O H 0.330(6) 0.450(3) 0.547(4) 0.094(18) Uiso 1 1 d D . . . .
H1O H 0.318(7) 0.329(5) 0.569(4) 0.11(2) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.338(4) . ?
C1 C2 1.379(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(5) . ?
C4 H4 0.9300 . ?
C5 N1 1.346(4) . ?
C5 C6 1.496(5) . ?
C6 N2 1.483(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.480(5) . ?
C7 C8 1.500(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N3 1.347(5) . ?
C8 C9 1.372(6) . ?
C9 C10 1.371(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.359(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(6) . ?
C11 H11 0.9300 . ?
C12 N3 1.335(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(5) . ?
C13 C18 1.391(5) . ?
C13 N2 1.465(4) . ?
C14 C15 1.382(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.390(5) . ?
C17 H17 0.9300 . ?
C18 O1 1.375(4) . ?
C19 O1 1.431(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
Co1 N1 2.115(3) . ?
Co1 N3 2.127(3) . ?
Co1 O2 2.132(3) . ?
Co1 N2 2.170(3) . ?
Co1 O1 2.223(2) . ?
Co1 I1 2.7008(5) . ?
O2 H2O 0.94(2) . ?
O2 H1O 0.93(2) . ?
Cl1 O4 1.340(8) . ?
Cl1 O6 1.340(7) . ?
Cl1 O5' 1.36(2) . ?
Cl1 O3 1.369(6) . ?
Cl1 O3' 1.380(17) . ?
Cl1 O4' 1.412(11) . ?
Cl1 O6' 1.413(15) . ?
Cl1 O5 1.442(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.8(4) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 118.6(4) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 119.6(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.3(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.3(3) . . ?
N1 C5 C6 116.0(3) . . ?
C4 C5 C6 122.7(3) . . ?
N2 C6 C5 109.6(3) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 108.3(3) . . ?
N2 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
N2 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
N3 C8 C9 121.7(4) . . ?
N3 C8 C7 115.4(3) . . ?
C9 C8 C7 122.9(4) . . ?
C10 C9 C8 118.6(5) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 118.5(5) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
N3 C12 C11 122.2(4) . . ?
N3 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C14 C13 C18 119.8(3) . . ?
C14 C13 N2 120.1(3) . . ?
C18 C13 N2 120.1(3) . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.1(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C17 C16 C15 121.6(4) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 119.7(4) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
O1 C18 C17 123.4(3) . . ?
O1 C18 C13 117.2(3) . . ?
C17 C18 C13 119.4(4) . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 Co1 N3 156.40(11) . . ?
N1 Co1 O2 93.03(11) . . ?
N3 Co1 O2 91.25(12) . . ?
N1 Co1 N2 78.49(10) . . ?
N3 Co1 N2 78.39(11) . . ?
O2 Co1 N2 89.03(10) . . ?
N1 Co1 O1 86.44(10) . . ?
N3 Co1 O1 84.08(10) . . ?
O2 Co1 O1 166.54(10) . . ?
N2 Co1 O1 77.68(9) . . ?
N1 Co1 I1 101.21(8) . . ?
N3 Co1 I1 101.70(8) . . ?
O2 Co1 I1 93.26(8) . . ?
N2 Co1 I1 177.70(7) . . ?
O1 Co1 I1 100.03(6) . . ?
C1 N1 C5 118.4(3) . . ?
C1 N1 Co1 127.5(2) . . ?
C5 N1 Co1 113.9(2) . . ?
C13 N2 C7 110.5(3) . . ?
C13 N2 C6 112.4(3) . . ?
C7 N2 C6 113.8(3) . . ?
C13 N2 Co1 110.9(2) . . ?
C7 N2 Co1 103.7(2) . . ?
C6 N2 Co1 105.0(2) . . ?
C12 N3 C8 118.7(3) . . ?
C12 N3 Co1 127.4(3) . . ?
C8 N3 Co1 113.0(2) . . ?
C18 O1 C19 117.9(3) . . ?
C18 O1 Co1 113.91(19) . . ?
C19 O1 Co1 126.4(3) . . ?
Co1 O2 H2O 115(3) . . ?
Co1 O2 H1O 111(4) . . ?
H2O O2 H1O 108(5) . . ?
O4 Cl1 O6 118.9(8) . . ?
O4 Cl1 O3 111.7(6) . . ?
O6 Cl1 O3 114.5(5) . . ?
O5' Cl1 O3' 109.8(14) . . ?
O5' Cl1 O4' 105.2(11) . . ?
O3' Cl1 O4' 93.9(10) . . ?
O5' Cl1 O6' 118.5(12) . . ?
O3' Cl1 O6' 110.0(10) . . ?
O4' Cl1 O6' 116.6(10) . . ?
O4 Cl1 O5 103.8(9) . . ?
O6 Cl1 O5 99.0(9) . . ?
O3 Cl1 O5 106.5(8) . . ?

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
N1 C1 C2 C3 1.1(6) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C3 C4 C5 -1.7(6) . . . . ?
C3 C4 C5 N1 1.8(5) . . . . ?
C3 C4 C5 C6 -176.1(3) . . . . ?
N1 C5 C6 N2 35.6(4) . . . . ?
C4 C5 C6 N2 -146.4(3) . . . . ?
N2 C7 C8 N3 -41.7(5) . . . . ?
N2 C7 C8 C9 137.8(4) . . . . ?
N3 C8 C9 C10 -0.6(8) . . . . ?
C7 C8 C9 C10 180.0(5) . . . . ?
C8 C9 C10 C11 -0.3(9) . . . . ?
C9 C10 C11 C12 0.6(9) . . . . ?
C10 C11 C12 N3 -0.2(8) . . . . ?
C18 C13 C14 C15 -1.1(6) . . . . ?
N2 C13 C14 C15 176.7(4) . . . . ?
C13 C14 C15 C16 0.2(7) . . . . ?
C14 C15 C16 C17 0.7(7) . . . . ?
C15 C16 C17 C18 -0.7(6) . . . . ?
C16 C17 C18 O1 179.1(3) . . . . ?
C16 C17 C18 C13 -0.2(5) . . . . ?
C14 C13 C18 O1 -178.3(3) . . . . ?
N2 C13 C18 O1 3.9(5) . . . . ?
C14 C13 C18 C17 1.1(5) . . . . ?
N2 C13 C18 C17 -176.7(3) . . . . ?
C2 C1 N1 C5 -1.0(5) . . . . ?
C2 C1 N1 Co1 -175.7(3) . . . . ?
C4 C5 N1 C1 -0.5(5) . . . . ?
C6 C5 N1 C1 177.5(3) . . . . ?
C4 C5 N1 Co1 174.9(3) . . . . ?
C6 C5 N1 Co1 -7.1(3) . . . . ?
C14 C13 N2 C7 -64.0(4) . . . . ?
C18 C13 N2 C7 113.8(3) . . . . ?
C14 C13 N2 C6 64.3(4) . . . . ?
C18 C13 N2 C6 -117.9(3) . . . . ?
C14 C13 N2 Co1 -178.5(3) . . . . ?
C18 C13 N2 Co1 -0.7(4) . . . . ?
C8 C7 N2 C13 -70.5(4) . . . . ?
C8 C7 N2 C6 161.9(3) . . . . ?
C8 C7 N2 Co1 48.5(3) . . . . ?
C5 C6 N2 C13 76.9(3) . . . . ?
C5 C6 N2 C7 -156.5(3) . . . . ?
C5 C6 N2 Co1 -43.8(3) . . . . ?
C11 C12 N3 C8 -0.7(6) . . . . ?
C11 C12 N3 Co1 167.2(4) . . . . ?
C9 C8 N3 C12 1.0(6) . . . . ?
C7 C8 N3 C12 -179.5(4) . . . . ?
C9 C8 N3 Co1 -168.5(4) . . . . ?
C7 C8 N3 Co1 11.0(4) . . . . ?
C17 C18 O1 C19 9.6(5) . . . . ?
C13 C18 O1 C19 -171.0(4) . . . . ?
C17 C18 O1 Co1 175.6(3) . . . . ?
C13 C18 O1 Co1 -5.0(4) . . . . ?

_refine_diff_density_max         0.824
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1527650'
loop_
_audit_author_name
_audit_author_address
'Anjana S'
;IIT Bombay
India
;
_audit_update_record             
;
2020-01-01 deposited with the CCDC.	2020-01-09 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         'C19 H19 Cl2 Co N3 O, 0.5H2O'
_chemical_formula_sum            'C19 H20 Cl2 Co N3 O1.50'
_chemical_formula_weight         444.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   9.5758(2)
_cell_length_b                   13.8028(3)
_cell_length_c                   15.2197(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2011.63(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3684
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      25.3

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.134
_shelx_estimated_absorpt_T_min   0.713
_shelx_estimated_absorpt_T_max   0.848
_exptl_absorpt_correction_type   0.multi-scan
_exptl_absorpt_correction_T_min  0.6598
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7230
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.992
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             3421
_reflns_number_gt                3213
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.930
_reflns_Friedel_fraction_full    0.930

_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_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)+(0.0265P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1270 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3421
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.0523
_refine_ls_wR_factor_gt          0.0514
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
C1 C 0.1176(3) 0.5551(3) 0.25612(18) 0.0531(8) Uani 1 1 d . . . . .
H1 H 0.081484 0.493001 0.249307 0.064 Uiso 1 1 calc R U . . .
C2 C 0.0317(4) 0.6278(3) 0.2879(2) 0.0701(11) Uani 1 1 d . . . . .
H2 H -0.060424 0.614548 0.303027 0.084 Uiso 1 1 calc R U . . .
C3 C 0.0843(4) 0.7193(3) 0.2966(2) 0.0757(12) Uani 1 1 d . . . . .
H3 H 0.028251 0.769122 0.317746 0.091 Uiso 1 1 calc R U . . .
C4 C 0.2210(4) 0.7371(3) 0.2737(2) 0.0605(9) Uani 1 1 d . . . . .
H4 H 0.257579 0.799341 0.277994 0.073 Uiso 1 1 calc R U . . .
C5 C 0.3032(3) 0.6618(2) 0.24425(17) 0.0409(7) Uani 1 1 d . . . . .
C6 C 0.4555(3) 0.6748(2) 0.22463(18) 0.0446(7) Uani 1 1 d . . . . .
H6A H 0.473112 0.741145 0.206672 0.053 Uiso 1 1 calc R U . . .
H6B H 0.510057 0.661816 0.277016 0.053 Uiso 1 1 calc R U . . .
C7 C 0.4592(3) 0.64463(19) 0.06580(16) 0.0343(6) Uani 1 1 d . . . . .
C8 C 0.5215(3) 0.7270(2) 0.03345(18) 0.0485(7) Uani 1 1 d . . . . .
H8 H 0.582532 0.762205 0.068696 0.058 Uiso 1 1 calc R U . . .
C9 C 0.4937(4) 0.7580(2) -0.0517(2) 0.0551(8) Uani 1 1 d . . . . .
H9 H 0.537867 0.812613 -0.074241 0.066 Uiso 1 1 calc R U . . .
C10 C 0.4002(3) 0.7069(2) -0.10226(18) 0.0495(7) Uani 1 1 d . . . . .
H10 H 0.381468 0.727683 -0.159189 0.059 Uiso 1 1 calc R U . . .
C11 C 0.3340(3) 0.6260(2) -0.07053(17) 0.0428(7) Uani 1 1 d . . . . .
H11 H 0.270210 0.592723 -0.105343 0.051 Uiso 1 1 calc R U . . .
C12 C 0.3634(3) 0.59415(19) 0.01465(17) 0.0346(6) Uani 1 1 d . . . . .
C13 C 0.6493(3) 0.5827(2) 0.1546(2) 0.0417(7) Uani 1 1 d . . . . .
H13A H 0.679575 0.569111 0.214154 0.050 Uiso 1 1 calc R U . . .
H13B H 0.704041 0.636321 0.131964 0.050 Uiso 1 1 calc R U . . .
C14 C 0.6683(3) 0.4945(2) 0.09751(18) 0.0404(7) Uani 1 1 d . . . . .
C15 C 0.7795(3) 0.4852(3) 0.0405(2) 0.0642(10) Uani 1 1 d . . . . .
H15 H 0.847075 0.533412 0.036107 0.077 Uiso 1 1 calc R U . . .
C16 C 0.7874(4) 0.4019(3) -0.0101(3) 0.0776(12) Uani 1 1 d . . . . .
H16 H 0.860890 0.393495 -0.049349 0.093 Uiso 1 1 calc R U . . .
C17 C 0.6874(4) 0.3323(3) -0.0022(2) 0.0659(10) Uani 1 1 d . . . . .
H17 H 0.692218 0.275773 -0.035282 0.079 Uiso 1 1 calc R U . . .
C18 C 0.5795(3) 0.3470(2) 0.05547(18) 0.0487(8) Uani 1 1 d . . . . .
H18 H 0.510676 0.299780 0.060326 0.058 Uiso 1 1 calc R U . . .
C21 C 0.2021(4) 0.4615(3) 0.0004(2) 0.0764(12) Uani 1 1 d . . . . .
H21A H 0.131242 0.505331 -0.019770 0.115 Uiso 1 1 calc R U . . .
H21B H 0.160173 0.412009 0.036045 0.115 Uiso 1 1 calc R U . . .
H21C H 0.247335 0.432128 -0.049215 0.115 Uiso 1 1 calc R U . . .
N1 N 0.2518(2) 0.57163(18) 0.23487(14) 0.0414(6) Uani 1 1 d . . . . .
N2 N 0.4976(2) 0.60741(15) 0.15333(13) 0.0337(5) Uani 1 1 d . . . . .
N3 N 0.5695(2) 0.42709(16) 0.10521(13) 0.0360(5) Uani 1 1 d . . . . .
O1 O 0.30244(19) 0.51326(14) 0.05105(11) 0.0416(5) Uani 1 1 d . . . . .
O2 O -0.1565(7) 0.4462(5) 0.3224(6) 0.142(3) Uani 0.5 1 d . . P . .
Cl1 Cl 0.51758(7) 0.45066(5) 0.32241(4) 0.04486(18) Uani 1 1 d . . . . .
Cl2 Cl 0.26824(7) 0.32572(5) 0.18568(5) 0.04732(18) Uani 1 1 d . . . . .
Co1 Co 0.39749(3) 0.46845(2) 0.18603(2) 0.03230(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.345(4) . ?
C1 C2 1.385(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 N1 1.346(4) . ?
C5 C6 1.499(4) . ?
C6 N2 1.485(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.376(4) . ?
C7 C12 1.390(4) . ?
C7 N2 1.475(3) . ?
C8 C9 1.391(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.398(4) . ?
C11 H11 0.9300 . ?
C12 O1 1.376(3) . ?
C13 N2 1.492(3) . ?
C13 C14 1.507(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N3 1.333(4) . ?
C14 C15 1.380(4) . ?
C15 C16 1.386(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.362(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(4) . ?
C17 H17 0.9300 . ?
C18 N3 1.343(3) . ?
C18 H18 0.9300 . ?
C21 O1 1.424(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 Co1 2.128(2) . ?
N2 Co1 2.201(2) . ?
N3 Co1 2.133(2) . ?
O1 Co1 2.3306(18) . ?
Cl1 Co1 2.3856(7) . ?
Cl2 Co1 2.3265(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.9(3) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 119.4(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.5(3) . . ?
N1 C5 C6 116.4(2) . . ?
C4 C5 C6 122.0(3) . . ?
N2 C6 C5 109.6(2) . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C12 120.0(2) . . ?
C8 C7 N2 120.2(2) . . ?
C12 C7 N2 119.7(2) . . ?
C7 C8 C9 120.3(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 119.3(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
O1 C12 C7 117.4(2) . . ?
O1 C12 C11 122.9(2) . . ?
C7 C12 C11 119.6(3) . . ?
N2 C13 C14 107.1(2) . . ?
N2 C13 H13A 110.3 . . ?
C14 C13 H13A 110.3 . . ?
N2 C13 H13B 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
N3 C14 C15 122.6(3) . . ?
N3 C14 C13 115.3(2) . . ?
C15 C14 C13 122.1(3) . . ?
C14 C15 C16 117.9(3) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 118.9(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
N3 C18 C17 122.5(3) . . ?
N3 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C5 118.7(3) . . ?
C1 N1 Co1 126.6(2) . . ?
C5 N1 Co1 114.62(18) . . ?
C7 N2 C6 112.0(2) . . ?
C7 N2 C13 109.5(2) . . ?
C6 N2 C13 113.5(2) . . ?
C7 N2 Co1 113.52(15) . . ?
C6 N2 Co1 105.22(16) . . ?
C13 N2 Co1 102.82(16) . . ?
C14 N3 C18 118.3(2) . . ?
C14 N3 Co1 114.35(17) . . ?
C18 N3 Co1 126.9(2) . . ?
C12 O1 C21 118.4(2) . . ?
C12 O1 Co1 113.86(14) . . ?
C21 O1 Co1 127.40(17) . . ?
N1 Co1 N3 152.46(9) . . ?
N1 Co1 N2 77.37(8) . . ?
N3 Co1 N2 76.50(8) . . ?
N1 Co1 Cl2 102.64(7) . . ?
N3 Co1 Cl2 100.53(6) . . ?
N2 Co1 Cl2 165.69(5) . . ?
N1 Co1 O1 82.77(8) . . ?
N3 Co1 O1 82.19(7) . . ?
N2 Co1 O1 74.90(7) . . ?
Cl2 Co1 O1 90.86(5) . . ?
N1 Co1 Cl1 94.64(6) . . ?
N3 Co1 Cl1 95.86(6) . . ?
N2 Co1 Cl1 94.38(5) . . ?
Cl2 Co1 Cl1 99.86(3) . . ?
O1 Co1 Cl1 169.28(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
N1 C1 C2 C3 1.0(5) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C3 C4 C5 -1.4(5) . . . . ?
C3 C4 C5 N1 2.0(5) . . . . ?
C3 C4 C5 C6 -175.4(3) . . . . ?
N1 C5 C6 N2 33.2(3) . . . . ?
C4 C5 C6 N2 -149.3(3) . . . . ?
C12 C7 C8 C9 -2.7(4) . . . . ?
N2 C7 C8 C9 174.9(3) . . . . ?
C7 C8 C9 C10 1.9(5) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C8 C7 C12 O1 -178.8(2) . . . . ?
N2 C7 C12 O1 3.5(4) . . . . ?
C8 C7 C12 C11 1.8(4) . . . . ?
N2 C7 C12 C11 -175.8(2) . . . . ?
C10 C11 C12 O1 -179.4(3) . . . . ?
C10 C11 C12 C7 -0.1(4) . . . . ?
N2 C13 C14 N3 -40.5(3) . . . . ?
N2 C13 C14 C15 138.7(3) . . . . ?
N3 C14 C15 C16 -0.2(5) . . . . ?
C13 C14 C15 C16 -179.3(3) . . . . ?
C14 C15 C16 C17 -0.2(6) . . . . ?
C15 C16 C17 C18 0.7(6) . . . . ?
C16 C17 C18 N3 -0.7(5) . . . . ?
C2 C1 N1 C5 -0.5(4) . . . . ?
C2 C1 N1 Co1 179.7(2) . . . . ?
C4 C5 N1 C1 -1.0(4) . . . . ?
C6 C5 N1 C1 176.5(2) . . . . ?
C4 C5 N1 Co1 178.8(2) . . . . ?
C6 C5 N1 Co1 -3.7(3) . . . . ?
C8 C7 N2 C6 65.9(3) . . . . ?
C12 C7 N2 C6 -116.4(3) . . . . ?
C8 C7 N2 C13 -60.8(3) . . . . ?
C12 C7 N2 C13 116.8(3) . . . . ?
C8 C7 N2 Co1 -175.1(2) . . . . ?
C12 C7 N2 Co1 2.5(3) . . . . ?
C5 C6 N2 C7 80.3(3) . . . . ?
C5 C6 N2 C13 -155.0(2) . . . . ?
C5 C6 N2 Co1 -43.4(2) . . . . ?
C14 C13 N2 C7 -70.0(3) . . . . ?
C14 C13 N2 C6 164.1(2) . . . . ?
C14 C13 N2 Co1 51.0(2) . . . . ?
C15 C14 N3 C18 0.2(4) . . . . ?
C13 C14 N3 C18 179.4(2) . . . . ?
C15 C14 N3 Co1 -172.7(2) . . . . ?
C13 C14 N3 Co1 6.5(3) . . . . ?
C17 C18 N3 C14 0.3(4) . . . . ?
C17 C18 N3 Co1 172.2(2) . . . . ?
C7 C12 O1 C21 178.9(3) . . . . ?
C11 C12 O1 C21 -1.8(4) . . . . ?
C7 C12 O1 Co1 -7.5(3) . . . . ?
C11 C12 O1 Co1 171.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O2 0.93 2.62 3.189(8) 120.3 . yes
C2 H2 O2 0.93 2.52 3.132(9) 123.9 . yes
C6 H6A Cl1 0.97 2.93 3.882(3) 168.6 3_655 yes
C13 H13A Cl1 0.97 2.79 3.382(3) 119.9 . yes
C17 H17 Cl2 0.93 2.78 3.627(3) 151.9 4 yes
C21 H21A Cl1 0.96 2.86 3.638(3) 139.1 2_564 yes
C21 H21B Cl2 0.96 2.77 3.444(3) 127.9 . yes
C1 H1 O2 0.93 2.62 3.189(8) 120.3 . yes
C2 H2 O2 0.93 2.52 3.132(9) 123.9 . yes
C6 H6A Cl1 0.97 2.93 3.882(3) 168.6 3_655 yes
C13 H13A Cl1 0.97 2.79 3.382(3) 119.9 . yes
C17 H17 Cl2 0.93 2.78 3.627(3) 151.9 4 yes
C21 H21A Cl1 0.96 2.86 3.638(3) 139.1 2_564 yes
C21 H21B Cl2 0.96 2.77 3.444(3) 127.9 . yes

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.034

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1527564'
_audit_update_record             
;
2017-01-15 deposited with the CCDC.	2020-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Cl2 Co N3 O2'
_chemical_formula_weight         438.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   13.7658(5)
_cell_length_b                   15.0676(6)
_cell_length_c                   8.9198(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1850.12(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4885
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      28.07

_exptl_crystal_description       rectangle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.234
_shelx_estimated_absorpt_T_min   0.724
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_T_max  0.887
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8405
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.004
_diffrn_reflns_theta_max         25.484
_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 0.900
_diffrn_reflns_point_group_measured_fraction_full 0.903
_reflns_number_total             3098
_reflns_number_gt                2908
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_max     0.785
_reflns_Friedel_fraction_full    0.792

_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       'APEXII (Bruker, 2012)'
_computing_cell_refinement       'APEXII/SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997) '
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)+(0.0318P)²+0.1604P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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_abs_structure_details 
;
 Flack x determined using 1110 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3098
_refine_ls_number_parameters     243
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_ref         0.0615
_refine_ls_wR_factor_gt          0.0599
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.053
_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
C1 C 0.8499(3) 0.5307(2) 0.9475(5) 0.0408(9) Uani 1 1 d . . . . .
H1 H 0.8197 0.5853 0.9614 0.049 Uiso 1 1 calc R U . . .
C2 C 0.9434(3) 0.5190(3) 0.9934(5) 0.0485(10) Uani 1 1 d . . . . .
H2 H 0.9761 0.5661 1.0381 0.058 Uiso 1 1 calc R U . . .
C3 C 0.9910(3) 0.4386(3) 0.9750(5) 0.0498(11) Uani 1 1 d . . . . .
H3 H 1.0548 0.4315 1.0075 0.060 Uiso 1 1 calc R U . . .
C4 C 0.9416(3) 0.3686(2) 0.9070(5) 0.0409(9) Uani 1 1 d . . . . .
H4 H 0.9722 0.3142 0.8927 0.049 Uiso 1 1 calc R U . . .
C5 C 0.8472(2) 0.3807(2) 0.8613(4) 0.0305(8) Uani 1 1 d . . . . .
C6 C 0.7990(3) 0.4609(2) 0.8795(4) 0.0310(8) Uani 1 1 d . . . . .
C7 C 0.8290(3) 0.2818(2) 0.6430(4) 0.0350(8) Uani 1 1 d . . . . .
H7A H 0.8994 0.2799 0.6478 0.042 Uiso 1 1 calc R U . . .
H7B H 0.8056 0.2232 0.6163 0.042 Uiso 1 1 calc R U . . .
C8 C 0.7973(3) 0.3477(2) 0.5292(4) 0.0350(8) Uani 1 1 d . . . . .
C9 C 0.8456(3) 0.3617(3) 0.3953(5) 0.0503(11) Uani 1 1 d . . . . .
H9 H 0.9023 0.3306 0.3741 0.060 Uiso 1 1 calc R U . . .
C10 C 0.8097(4) 0.4214(3) 0.2944(5) 0.0615(13) Uani 1 1 d . . . . .
H10 H 0.8411 0.4308 0.2035 0.074 Uiso 1 1 calc R U . . .
C11 C 0.7258(4) 0.4678(3) 0.3292(5) 0.0595(12) Uani 1 1 d . . . . .
H11 H 0.7007 0.5093 0.2624 0.071 Uiso 1 1 calc R U . . .
C12 C 0.6800(3) 0.4518(3) 0.4638(5) 0.0464(10) Uani 1 1 d . . . . .
H12 H 0.6236 0.4829 0.4873 0.056 Uiso 1 1 calc R U . . .
C13 C 0.7751(3) 0.2330(2) 0.8955(4) 0.0397(9) Uani 1 1 d . . . . .
H13A H 0.8358 0.2193 0.9455 0.048 Uiso 1 1 calc R U . . .
H13B H 0.7540 0.1808 0.8407 0.048 Uiso 1 1 calc R U . . .
C14 C 0.7001(3) 0.2591(2) 1.0077(4) 0.0388(8) Uani 1 1 d . . . . .
C15 C 0.5661(3) 0.3477(3) 1.0516(5) 0.0465(10) Uani 1 1 d . . . . .
H15 H 0.5236 0.3918 1.0196 0.056 Uiso 1 1 calc R U . . .
C16 C 0.5561(4) 0.3133(3) 1.1947(5) 0.0619(13) Uani 1 1 d . . . . .
H16 H 0.5061 0.3327 1.2568 0.074 Uiso 1 1 calc R U . . .
C17 C 0.6199(4) 0.2510(3) 1.2431(6) 0.0698(13) Uani 1 1 d . . . . .
H17 H 0.6137 0.2272 1.3388 0.084 Uiso 1 1 calc R U . . .
C18 C 0.6939(4) 0.2231(3) 1.1503(5) 0.0583(11) Uani 1 1 d . . . . .
H18 H 0.7387 0.1810 1.1827 0.070 Uiso 1 1 calc R U . . .
Cl1 Cl 0.60323(7) 0.23377(6) 0.65646(11) 0.0428(2) Uani 1 1 d . . . . .
Cl2 Cl 0.51499(7) 0.42735(7) 0.72457(13) 0.0545(3) Uani 1 1 d . . . . .
Co1 Co 0.66064(3) 0.36106(2) 0.75548(6) 0.02941(13) Uani 1 1 d . . . . .
N2 N 0.78853(19) 0.30897(16) 0.7909(3) 0.0283(7) Uani 1 1 d . . . . .
N1 N 0.7150(2) 0.39227(18) 0.5617(3) 0.0336(7) Uani 1 1 d . . . . .
N3 N 0.6354(2) 0.3192(2) 0.9585(3) 0.0369(7) Uani 1 1 d . . . . .
O1 O 0.70780(18) 0.46893(14) 0.8343(3) 0.0356(6) Uani 1 1 d . . . . .
O2 O 0.6177(3) 0.6254(2) 0.9293(5) 0.0587(8) Uani 1 1 d . . . . .
H2O H 0.640(4) 0.575(4) 0.880(6) 0.073(16) Uiso 1 1 d . . . . .
H1O H 0.578(4) 0.616(3) 1.003(7) 0.08(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.362(6) . ?
C1 C6 1.402(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.388(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(5) . ?
C5 N2 1.489(4) . ?
C6 O1 1.324(4) . ?
C7 C8 1.485(5) . ?
C7 N2 1.490(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.349(5) . ?
C8 C9 1.383(6) . ?
C9 C10 1.366(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(6) . ?
C11 H11 0.9300 . ?
C12 N1 1.341(5) . ?
C12 H12 0.9300 . ?
C13 N2 1.489(4) . ?
C13 C14 1.490(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N3 1.344(5) . ?
C14 C18 1.386(6) . ?
C15 N3 1.336(5) . ?
C15 C16 1.384(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.356(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
Cl1 Co1 2.2546(9) . ?
Cl2 Co1 2.2569(10) . ?
Co1 O1 1.886(2) . ?
Co1 N1 1.941(3) . ?
Co1 N3 1.948(3) . ?
Co1 N2 1.953(3) . ?
O2 H2O 0.93(5) . ?
O2 H1O 0.87(6) . ?

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
C2 C1 C6 120.3(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 121.6(4) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 118.8(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 122.3(3) . . ?
C4 C5 N2 122.8(3) . . ?
C6 C5 N2 114.9(3) . . ?
O1 C6 C5 119.8(3) . . ?
O1 C6 C1 122.5(3) . . ?
C5 C6 C1 117.7(3) . . ?
C8 C7 N2 108.2(3) . . ?
C8 C7 H7A 110.1 . . ?
N2 C7 H7A 110.1 . . ?
C8 C7 H7B 110.1 . . ?
N2 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
N1 C8 C9 120.9(4) . . ?
N1 C8 C7 115.6(3) . . ?
C9 C8 C7 123.4(4) . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 119.1(4) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 119.2(4) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
N1 C12 C11 121.3(4) . . ?
N1 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
N2 C13 C14 107.7(3) . . ?
N2 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
N2 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
N3 C14 C18 121.6(4) . . ?
N3 C14 C13 114.7(3) . . ?
C18 C14 C13 123.7(4) . . ?
N3 C15 C16 121.6(4) . . ?
N3 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C15 119.2(4) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 120.0(5) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C14 118.4(5) . . ?
C17 C18 H18 120.8 . . ?
C14 C18 H18 120.8 . . ?
O1 Co1 N1 89.46(11) . . ?
O1 Co1 N3 89.63(12) . . ?
N1 Co1 N3 167.03(13) . . ?
O1 Co1 N2 88.61(10) . . ?
N1 Co1 N2 83.92(12) . . ?
N3 Co1 N2 83.11(12) . . ?
O1 Co1 Cl1 178.69(9) . . ?
N1 Co1 Cl1 89.56(8) . . ?
N3 Co1 Cl1 91.51(9) . . ?
N2 Co1 Cl1 92.15(8) . . ?
O1 Co1 Cl2 88.28(8) . . ?
N1 Co1 Cl2 97.26(9) . . ?
N3 Co1 Cl2 95.65(10) . . ?
N2 Co1 Cl2 176.65(8) . . ?
Cl1 Co1 Cl2 90.99(4) . . ?
C13 N2 C5 111.2(3) . . ?
C13 N2 C7 113.0(2) . . ?
C5 N2 C7 111.7(2) . . ?
C13 N2 Co1 107.3(2) . . ?
C5 N2 Co1 105.41(18) . . ?
C7 N2 Co1 107.7(2) . . ?
C12 N1 C8 119.7(3) . . ?
C12 N1 Co1 127.1(3) . . ?
C8 N1 Co1 113.2(2) . . ?
C15 N3 C14 119.1(4) . . ?
C15 N3 Co1 126.9(3) . . ?
C14 N3 Co1 113.8(2) . . ?
C6 O1 Co1 111.18(19) . . ?
H2O O2 H1O 115(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
C6 C1 C2 C3 -0.1(6) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
C3 C4 C5 N2 -178.6(4) . . . . ?
C4 C5 C6 O1 -179.6(3) . . . . ?
N2 C5 C6 O1 -0.5(5) . . . . ?
C4 C5 C6 C1 -0.2(6) . . . . ?
N2 C5 C6 C1 179.0(3) . . . . ?
C2 C1 C6 O1 179.4(4) . . . . ?
C2 C1 C6 C5 0.0(6) . . . . ?
N2 C7 C8 N1 -25.0(4) . . . . ?
N2 C7 C8 C9 157.2(3) . . . . ?
N1 C8 C9 C10 0.0(6) . . . . ?
C7 C8 C9 C10 177.7(4) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C10 C11 C12 N1 0.0(6) . . . . ?
N2 C13 C14 N3 27.5(4) . . . . ?
N2 C13 C14 C18 -154.5(4) . . . . ?
N3 C15 C16 C17 2.0(6) . . . . ?
C15 C16 C17 C18 0.3(7) . . . . ?
C16 C17 C18 C14 -0.9(7) . . . . ?
N3 C14 C18 C17 -0.7(6) . . . . ?
C13 C14 C18 C17 -178.5(4) . . . . ?
C14 C13 N2 C5 76.4(3) . . . . ?
C14 C13 N2 C7 -157.0(3) . . . . ?
C14 C13 N2 Co1 -38.4(3) . . . . ?
C4 C5 N2 C13 62.1(4) . . . . ?
C6 C5 N2 C13 -117.0(3) . . . . ?
C4 C5 N2 C7 -65.1(4) . . . . ?
C6 C5 N2 C7 115.7(3) . . . . ?
C4 C5 N2 Co1 178.2(3) . . . . ?
C6 C5 N2 Co1 -1.0(3) . . . . ?
C8 C7 N2 C13 153.7(3) . . . . ?
C8 C7 N2 C5 -80.0(3) . . . . ?
C8 C7 N2 Co1 35.3(3) . . . . ?
C11 C12 N1 C8 0.8(5) . . . . ?
C11 C12 N1 Co1 -180.0(3) . . . . ?
C9 C8 N1 C12 -0.8(5) . . . . ?
C7 C8 N1 C12 -178.7(3) . . . . ?
C9 C8 N1 Co1 179.9(3) . . . . ?
C7 C8 N1 Co1 2.0(4) . . . . ?
C16 C15 N3 C14 -3.6(6) . . . . ?
C16 C15 N3 Co1 -179.3(3) . . . . ?
C18 C14 N3 C15 2.9(5) . . . . ?
C13 C14 N3 C15 -179.1(3) . . . . ?
C18 C14 N3 Co1 179.1(3) . . . . ?
C13 C14 N3 Co1 -2.8(4) . . . . ?
C5 C6 O1 Co1 1.7(4) . . . . ?
C1 C6 O1 Co1 -177.7(3) . . . . ?
N1 Co1 O1 C6 -85.8(2) . . . . ?
N3 Co1 O1 C6 81.3(2) . . . . ?
N2 Co1 O1 C6 -1.8(2) . . . . ?
Cl2 Co1 O1 C6 177.0(2) . . . . ?

_refine_diff_density_max         0.636
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.047

