# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_pb_5250
_database_code_depnum_ccdc_archive 'CCDC 2161673'
loop_
_audit_author_name
_audit_author_address
'Paulina Bourosh'
;Institute of Applied Physics
Moldova
;
_audit_update_record             
;
2022-03-24 deposited with the CCDC.	2022-05-24 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            'C22.50 H22.50 Fe N7.50 O3.50'
_chemical_formula_weight         509.83

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 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, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.377(3)
_cell_length_b                   9.4953(13)
_cell_length_c                   10.2036(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1199.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    351
_cell_measurement_theta_min      3.3600
_cell_measurement_theta_max      20.1410

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.671
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   CrysAlis
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9914
_diffrn_reflns_number            3179
_diffrn_reflns_av_unetI/netI     0.1691
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.361
_diffrn_reflns_theta_max         25.042
_diffrn_reflns_theta_full        25.042
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             2036
_reflns_number_gt                1199
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_max     0.915
_reflns_Friedel_fraction_full    0.915

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=exp[0.2000(sinθ/λ)²)]/[σ²(Fo²)+(0.0231P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 270 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2036
_refine_ls_number_parameters     162
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1393
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.014
_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
Fe1 Fe 1.0000 0.0000 0.33695(18) 0.0353(6) Uani 1 2 d S T P . .
N1 N 0.5897(7) 0.2918(7) 0.6647(9) 0.037(2) Uani 1 1 d . . . . .
N2 N 0.7797(7) 0.1584(8) 0.3491(8) 0.040(2) Uani 1 1 d . . . . .
N3 N 0.8551(8) 0.1088(8) 0.2600(8) 0.041(2) Uani 1 1 d . . . . .
N4 N 1.0000 0.0000 0.1182(10) 0.037(3) Uani 1 2 d S T P . .
O1 O 0.8997(6) 0.0623(6) 0.4994(7) 0.0387(19) Uani 1 1 d . . . . .
C1 C 0.8113(10) 0.1226(10) 0.4700(10) 0.039(3) Uani 1 1 d . . . . .
C2 C 0.7288(9) 0.1467(11) 0.5725(10) 0.036(3) Uani 1 1 d . . . . .
C3 C 0.6626(9) 0.2641(10) 0.5740(10) 0.040(3) Uani 1 1 d . . . . .
H3 H 0.6701 0.3284 0.5059 0.048 Uiso 1 1 calc R U . . .
C4 C 0.5781(8) 0.1969(9) 0.7595(9) 0.038(3) Uani 1 1 d . . . . .
H4 H 0.5274 0.2137 0.8249 0.046 Uiso 1 1 calc R U . . .
C5 C 0.6382(9) 0.0742(9) 0.7650(10) 0.045(3) Uani 1 1 d . . . . .
H5 H 0.6255 0.0084 0.8307 0.054 Uiso 1 1 calc R U . . .
C6 C 0.7163(9) 0.0506(9) 0.6730(11) 0.045(3) Uani 1 1 d . . . . .
H6 H 0.7602 -0.0286 0.6780 0.054 Uiso 1 1 calc R U . . .
C7 C 0.8387(10) 0.1304(10) 0.1379(10) 0.042(3) Uani 1 1 d . . . . .
C8 C 0.9217(10) 0.0650(9) 0.0516(10) 0.039(3) Uani 1 1 d . . . . .
C9 C 0.9207(10) 0.0669(10) -0.0846(11) 0.049(3) Uani 1 1 d . . . . .
H9 H 0.8658 0.1140 -0.1289 0.059 Uiso 1 1 calc R U . . .
C10 C 1.0000 0.0000 -0.1537(14) 0.056(4) Uani 1 2 d S T P . .
H10 H 1.0000 0.0000 -0.2449 0.067 Uiso 1 2 calc R U P . .
C11 C 0.7457(10) 0.2124(11) 0.0807(11) 0.064(4) Uani 1 1 d . . . . .
H11A H 0.6986 0.1494 0.0343 0.096 Uiso 1 1 calc R U . . .
H11B H 0.7730 0.2823 0.0213 0.096 Uiso 1 1 calc R U . . .
H11C H 0.7064 0.2576 0.1500 0.096 Uiso 1 1 calc R U . . .
N1D N 0.5000 0.0000 0.2598(15) 0.017(4) Uiso 0.5 2 d DS . P A 1
O1D O 0.453(3) 0.080(3) 0.061(3) 0.094(14) Uiso 0.25 1 d D . P A 1
C1D C 0.5000 0.0000 0.131(2) 0.122(16) Uiso 0.5 2 d DS . P A 1
H1D H 0.5629 0.0627 0.1312 0.146 Uiso 0.25 1 calc R U P A 1
C2D C 0.454(2) 0.095(2) 0.347(2) 0.097(10) Uiso 0.5 1 d D . P A 1
H2D1 H 0.3812 0.1161 0.3197 0.146 Uiso 0.5 1 calc R U P A 1
H2D2 H 0.4954 0.1800 0.3491 0.146 Uiso 0.5 1 calc R U P A 1
H2D3 H 0.4519 0.0541 0.4333 0.146 Uiso 0.5 1 calc R U P A 1
O1W O 0.443(4) 0.078(5) 0.240(5) 0.16(2) Uiso 0.25 1 d . . P B 2
H1W1 H 0.4910 0.0324 0.2855 0.238 Uiso 0.25 1 d R U P B 2
H2W1 H 0.4649 0.1352 0.1968 0.238 Uiso 0.25 1 d R U P B 2
O2W O 0.5000 0.0000 0.038(3) 0.117(10) Uiso 0.5 2 d S . P C 2
H1W2 H 0.4789 0.0683 0.0071 0.176 Uiso 0.5 1 d R U P C 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O1 2.154(7) . ?
Fe1 O1 2.154(7) 2_755 ?
Fe1 N3 2.214(9) . ?
Fe1 N3 2.214(9) 2_755 ?
Fe1 N4 2.232(10) . ?
Fe1 N1 2.267(7) 4_556 ?
Fe1 N1 2.267(7) 3_646 ?
N1 C3 1.319(12) . ?
N1 C4 1.330(11) . ?
N1 Fe1 2.267(7) 3_656 ?
N2 C1 1.339(11) . ?
N2 N3 1.385(11) . ?
N3 C7 1.279(11) . ?
N4 C8 1.336(12) . ?
N4 C8 1.336(12) 2_755 ?
O1 C1 1.270(12) . ?
C1 C2 1.479(14) . ?
C2 C6 1.381(13) . ?
C2 C3 1.384(12) . ?
C4 C5 1.383(12) . ?
C5 C6 1.366(13) . ?
C7 C8 1.488(14) . ?
C7 C11 1.507(14) . ?
C8 C9 1.390(13) . ?
C9 C10 1.365(13) . ?
C10 C9 1.365(13) 2_755 ?
N1D C1D 1.31(2) . ?
N1D C2D 1.393(17) . ?
N1D C2D 1.393(17) 2_655 ?
O1D C1D 1.19(2) . ?
C1D O1D 1.19(2) 2_655 ?

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
O1 Fe1 O1 79.4(4) . 2_755 ?
O1 Fe1 N3 71.2(3) . . ?
O1 Fe1 N3 150.3(3) 2_755 . ?
O1 Fe1 N3 150.3(3) . 2_755 ?
O1 Fe1 N3 71.2(3) 2_755 2_755 ?
N3 Fe1 N3 138.4(4) . 2_755 ?
O1 Fe1 N4 140.31(19) . . ?
O1 Fe1 N4 140.31(19) 2_755 . ?
N3 Fe1 N4 69.2(2) . . ?
N3 Fe1 N4 69.2(2) 2_755 . ?
O1 Fe1 N1 92.8(3) . 4_556 ?
O1 Fe1 N1 87.9(3) 2_755 4_556 ?
N3 Fe1 N1 89.3(3) . 4_556 ?
N3 Fe1 N1 90.4(3) 2_755 4_556 ?
N4 Fe1 N1 89.6(2) . 4_556 ?
O1 Fe1 N1 87.9(3) . 3_646 ?
O1 Fe1 N1 92.8(3) 2_755 3_646 ?
N3 Fe1 N1 90.4(3) . 3_646 ?
N3 Fe1 N1 89.3(3) 2_755 3_646 ?
N4 Fe1 N1 89.6(2) . 3_646 ?
N1 Fe1 N1 179.2(5) 4_556 3_646 ?
C3 N1 C4 116.6(8) . . ?
C3 N1 Fe1 120.3(7) . 3_656 ?
C4 N1 Fe1 122.9(7) . 3_656 ?
C1 N2 N3 108.8(8) . . ?
C7 N3 N2 118.6(10) . . ?
C7 N3 Fe1 123.3(8) . . ?
N2 N3 Fe1 118.1(6) . . ?
C8 N4 C8 118.8(12) . 2_755 ?
C8 N4 Fe1 120.6(6) . . ?
C8 N4 Fe1 120.6(6) 2_755 . ?
C1 O1 Fe1 116.0(7) . . ?
O1 C1 N2 125.7(10) . . ?
O1 C1 C2 119.8(9) . . ?
N2 C1 C2 114.2(10) . . ?
C6 C2 C3 117.2(10) . . ?
C6 C2 C1 120.0(9) . . ?
C3 C2 C1 122.8(10) . . ?
N1 C3 C2 125.0(10) . . ?
N1 C4 C5 122.9(9) . . ?
C6 C5 C4 119.4(9) . . ?
C5 C6 C2 118.8(9) . . ?
N3 C7 C8 113.6(10) . . ?
N3 C7 C11 125.5(11) . . ?
C8 C7 C11 120.9(9) . . ?
N4 C8 C9 121.4(11) . . ?
N4 C8 C7 113.1(9) . . ?
C9 C8 C7 125.5(11) . . ?
C10 C9 C8 120.3(12) . . ?
C9 C10 C9 117.8(15) 2_755 . ?
C1D N1D C2D 129.8(12) . . ?
C1D N1D C2D 129.8(12) . 2_655 ?
C2D N1D C2D 100(2) . 2_655 ?
O1D C1D O1D 107(4) 2_655 . ?
O1D C1D N1D 127(2) 2_655 . ?
O1D C1D N1D 127(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
C3 H3 O1 0.93 2.38 3.029(11) 126.3 3_656
C5 H5 O2W 0.93 2.63 3.34(2) 134.5 1_556
O1W H1W1 O1W 0.87 1.41 2.06(9) 127.0 2_655

_refine_diff_density_max         0.857
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_pb_4679
_database_code_depnum_ccdc_archive 'CCDC 2161674'
loop_
_audit_author_name
_audit_author_address
'Paulina Bourosh'
;Institute of Applied Physics
Moldova
;
_audit_update_record             
;
2022-03-24 deposited with the CCDC.	2022-05-24 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            'C24 H24 Co N8 O3'
_chemical_formula_weight         531.44

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 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, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   12.2124(5)
_cell_length_b                   9.4700(4)
_cell_length_c                   10.2670(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1187.39(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    885
_cell_measurement_theta_min      3.3580
_cell_measurement_theta_max      24.8190

_exptl_crystal_description       plate
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             550
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.767
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85475
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   CrysAlis
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9914
_diffrn_reflns_number            2653
_diffrn_reflns_av_unetI/netI     0.0758
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.926
_diffrn_reflns_theta_max         25.092
_diffrn_reflns_theta_full        25.092
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_point_group_measured_fraction_full 0.882
_reflns_number_total             1875
_reflns_number_gt                1612
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.521
_reflns_Friedel_fraction_max     0.730
_reflns_Friedel_fraction_full    0.730

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0228P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 483 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1875
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.0000 0.0000 0.33344(9) 0.0236(3) Uani 1 2 d S T P . .
O1 O 0.0993(3) -0.0638(3) 0.4974(4) 0.0307(9) Uani 1 1 d . . . . .
N1 N 0.4113(3) -0.2954(4) 0.6662(4) 0.0284(10) Uani 1 1 d . . . . .
N2 N 0.2224(3) -0.1592(4) 0.3484(5) 0.0315(11) Uani 1 1 d . . . . .
N3 N 0.1458(3) -0.1104(4) 0.2601(4) 0.0257(10) Uani 1 1 d . . . . .
N4 N 0.0000 0.0000 0.1184(5) 0.0261(12) Uani 1 2 d S T P . .
C1 C 0.1885(4) -0.1229(5) 0.4673(5) 0.0256(12) Uani 1 1 d . . . . .
C2 C 0.2706(4) -0.1489(5) 0.5729(5) 0.0273(13) Uani 1 1 d . . . . .
C3 C 0.3371(4) -0.2671(5) 0.5743(5) 0.0322(14) Uani 1 1 d . . . . .
H3 H 0.3296 -0.3315 0.5065 0.039 Uiso 1 1 calc R U . . .
C4 C 0.4225(4) -0.1992(5) 0.7600(5) 0.0314(13) Uani 1 1 d . . . . .
H4 H 0.4741 -0.2158 0.8248 0.038 Uiso 1 1 calc R U . . .
C5 C 0.3623(4) -0.0774(5) 0.7661(5) 0.0354(14) Uani 1 1 d . . . . .
H5 H 0.3744 -0.0124 0.8324 0.042 Uiso 1 1 calc R U . . .
C6 C 0.2837(4) -0.0525(5) 0.6726(5) 0.0335(13) Uani 1 1 d . . . . .
H6 H 0.2401 0.0279 0.6767 0.040 Uiso 1 1 calc R U . . .
C7 C 0.1630(4) -0.1315(5) 0.1387(5) 0.0288(13) Uani 1 1 d . . . . .
C8 C 0.0809(4) -0.0657(5) 0.0539(5) 0.0273(12) Uani 1 1 d . . . . .
C9 C 0.0825(5) -0.0669(5) -0.0826(5) 0.0377(14) Uani 1 1 d . . . . .
H9 H 0.1387 -0.1122 -0.1272 0.045 Uiso 1 1 calc R U . . .
C10 C 0.0000 0.0000 -0.1495(7) 0.0422(17) Uani 1 2 d S T P . .
H10 H 0.0000 0.0000 -0.2401 0.051 Uiso 1 2 d R U P . .
C11 C 0.2575(5) -0.2136(6) 0.0830(6) 0.0496(17) Uani 1 1 d . . . . .
H11A H 0.3056 -0.1505 0.0373 0.074 Uiso 1 1 calc R U . . .
H11B H 0.2304 -0.2839 0.0239 0.074 Uiso 1 1 calc R U . . .
H11C H 0.2970 -0.2587 0.1524 0.074 Uiso 1 1 calc R U . . .
O1D O 0.477(2) 0.0477(15) 0.0423(10) 0.131(10) Uani 0.5 1 d . . P A -1
N1D N 0.506(8) 0.003(6) 0.2544(13) 0.072(7) Uani 0.5 1 d . . P A -1
C1D C 0.469(3) 0.036(8) 0.1345(18) 0.20(4) Uani 0.5 1 d . . P A -1
H1D H 0.3958 0.0601 0.1491 0.246 Uiso 0.5 1 calc R U P A -1
C2D C 0.458(2) 0.085(3) 0.368(3) 0.134(14) Uani 0.5 1 d . . P A -1
H2D1 H 0.3802 0.0717 0.3703 0.200 Uiso 0.5 1 calc R U P A -1
H2D2 H 0.4741 0.1837 0.3572 0.200 Uiso 0.5 1 calc R U P A -1
H2D3 H 0.4898 0.0519 0.4477 0.200 Uiso 0.5 1 calc R U P A -1
C3D C 0.562(3) -0.110(3) 0.286(3) 0.21(2) Uani 0.5 1 d . . P A -1
H3D1 H 0.6133 -0.1305 0.2178 0.308 Uiso 0.5 1 calc R U P A -1
H3D2 H 0.5128 -0.1879 0.2966 0.308 Uiso 0.5 1 calc R U P A -1
H3D3 H 0.6003 -0.0929 0.3657 0.308 Uiso 0.5 1 calc R U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.161(3) . ?
Co1 O1 2.161(3) 2 ?
Co1 N3 2.198(4) 2 ?
Co1 N3 2.198(4) . ?
Co1 N4 2.208(5) . ?
Co1 N1 2.220(4) 3_446 ?
Co1 N1 2.220(4) 4_556 ?
O1 C1 1.263(5) . ?
N1 C4 1.332(6) . ?
N1 C3 1.335(6) . ?
N1 Co1 2.220(4) 3_546 ?
N2 C1 1.335(6) . ?
N2 N3 1.381(5) . ?
N3 C7 1.281(6) . ?
N4 C8 1.342(5) 2 ?
N4 C8 1.342(5) . ?
C1 C2 1.497(7) . ?
C2 C6 1.382(7) . ?
C2 C3 1.383(7) . ?
C4 C5 1.369(6) . ?
C5 C6 1.378(7) . ?
C7 C8 1.467(7) . ?
C7 C11 1.504(7) . ?
C8 C9 1.401(6) . ?
C9 C10 1.375(6) . ?
C10 C9 1.375(6) 2 ?
O1D C1D 0.959(17) . ?
N1D C3D 1.31(8) . ?
N1D C1D 1.35(5) . ?
N1D C2D 1.52(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
O1 Co1 O1 77.65(18) . 2 ?
O1 Co1 N3 148.70(14) . 2 ?
O1 Co1 N3 71.28(14) 2 2 ?
O1 Co1 N3 71.28(14) . . ?
O1 Co1 N3 148.70(14) 2 . ?
N3 Co1 N3 140.0(2) 2 . ?
O1 Co1 N4 141.17(9) . . ?
O1 Co1 N4 141.17(9) 2 . ?
N3 Co1 N4 69.98(11) 2 . ?
N3 Co1 N4 69.98(11) . . ?
O1 Co1 N1 91.65(14) . 3_446 ?
O1 Co1 N1 88.21(14) 2 3_446 ?
N3 Co1 N1 91.15(15) 2 3_446 ?
N3 Co1 N1 88.92(14) . 3_446 ?
N4 Co1 N1 90.09(12) . 3_446 ?
O1 Co1 N1 88.21(14) . 4_556 ?
O1 Co1 N1 91.65(14) 2 4_556 ?
N3 Co1 N1 88.92(14) 2 4_556 ?
N3 Co1 N1 91.15(14) . 4_556 ?
N4 Co1 N1 90.09(12) . 4_556 ?
N1 Co1 N1 179.8(2) 3_446 4_556 ?
C1 O1 Co1 114.7(4) . . ?
C4 N1 C3 116.4(4) . . ?
C4 N1 Co1 123.0(3) . 3_546 ?
C3 N1 Co1 120.5(3) . 3_546 ?
C1 N2 N3 107.7(4) . . ?
C7 N3 N2 118.4(4) . . ?
C7 N3 Co1 122.7(4) . . ?
N2 N3 Co1 118.9(3) . . ?
C8 N4 C8 120.9(6) 2 . ?
C8 N4 Co1 119.6(3) 2 . ?
C8 N4 Co1 119.6(3) . . ?
O1 C1 N2 127.2(5) . . ?
O1 C1 C2 118.3(5) . . ?
N2 C1 C2 114.4(4) . . ?
C6 C2 C3 117.3(5) . . ?
C6 C2 C1 120.3(4) . . ?
C3 C2 C1 122.3(5) . . ?
N1 C3 C2 124.6(5) . . ?
N1 C4 C5 123.6(5) . . ?
C4 C5 C6 119.1(5) . . ?
C5 C6 C2 118.9(5) . . ?
N3 C7 C8 113.6(5) . . ?
N3 C7 C11 125.2(5) . . ?
C8 C7 C11 121.3(5) . . ?
N4 C8 C9 120.5(5) . . ?
N4 C8 C7 114.0(5) . . ?
C9 C8 C7 125.5(5) . . ?
C10 C9 C8 119.1(6) . . ?
C9 C10 C9 120.0(7) . 2 ?
C3D N1D C1D 126(5) . . ?
C3D N1D C2D 115(3) . . ?
C1D N1D C2D 117(7) . . ?
O1D C1D N1D 153(6) . . ?

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
C3 H3 O1 0.93 2.37 3.006(6) 125.9 4_546
C5 H5 O1D 0.93 2.56 3.376(16) 147.4 1_556

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.059

