# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_Ni
_database_code_depnum_ccdc_archive 'CCDC 2376992'
_audit_update_record             
;
2024-09-12 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_audit_creation_date             2024-09-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H11 N Ni O6'
_chemical_formula_sum            'C11 H11 N Ni O6'
_chemical_formula_weight         311.92
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
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'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   17.078(2)
_cell_length_b                   9.7734(14)
_cell_length_c                   7.2286(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.954(5)
_cell_angle_gamma                90
_cell_volume                     1175.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7165
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.864
_shelx_estimated_absorpt_T_min   0.812
_exptl_absorpt_coefficient_mu    1.673
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1450 before and 0.0724 after correction.
The Ratio of minimum to maximum transmission is 0.6774.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9881
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.417
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1363
_reflns_number_total             1410
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.652
_refine_diff_density_min         -2.151
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1410
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0555
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0647P)²+9.1590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1404
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 C5-O2 \\sim C5-O4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim
Ueq: with sigma of 0 and sigma for terminal atoms of 0.01
Uanis(O2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(O4) \\sim Ueq, Uanis(O2) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C5) = Uanis(C4) = Uanis(C3) = Uanis(C2)
Uanis(O2) = Uanis(O4)
4. Others
 Sof(O4)=0.5*(1-FVAR(2))
 Sof(O2)=0.5*FVAR(2)
 Fixed Sof: H4B(0.5) H4A(0.5)
5.a Rotating group:
 O1(H1A,H1B)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4B,H4A)
5.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C1(H1), C2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.24894(3) 0.500000 0.59425(8) 0.0182(2) Uani 1 2 d S T P . .
O5 O 0.17339(14) 0.6112(3) 1.3696(4) 0.0254(5) Uani 1 1 d . . . . .
O3 O 0.1511(6) 0.500000 0.7151(8) 0.0353(16) Uani 1 2 d S T P A .
O1 O 0.30338(16) 0.6460(3) 0.7825(4) 0.0312(6) Uani 1 1 d . . . . .
H1A H 0.310458 0.645214 0.903716 0.047 Uiso 1 1 d R U . . .
H1B H 0.324452 0.721557 0.758077 0.047 Uiso 1 1 d R U . . .
N1 N 0.3388(2) 0.500000 0.4455(6) 0.0233(8) Uani 1 2 d S T P A .
C8 C 0.0716(3) 0.500000 1.1380(6) 0.0199(9) Uani 1 2 d S T P . .
C9 C 0.1452(3) 0.500000 1.2974(6) 0.0192(9) Uani 1 2 d S T P . .
C6 C 0.0739(3) 0.500000 0.9461(7) 0.0235(10) Uani 1 2 d S T P A .
C7 C 0.0019(3) 0.500000 0.8099(7) 0.0237(10) Uani 1 2 d S T P . .
H7 H 0.003076 0.500000 0.681926 0.028 Uiso 1 2 calc R U P . .
C1 C 0.3667(2) 0.6171(5) 0.3875(6) 0.0354(9) Uani 1 1 d . . . . .
H1 H 0.348126 0.699582 0.425407 0.043 Uiso 1 1 calc R U . A .
C5 C 0.1529(4) 0.500000 0.8868(9) 0.0518(9) Uani 1 2 d DS T P . .
C3 C 0.4510(4) 0.500000 0.2163(9) 0.0518(9) Uani 1 2 d S T P . .
C2 C 0.4218(3) 0.6202(7) 0.2741(6) 0.0518(9) Uani 1 1 d . . . . .
H2 H 0.439176 0.703725 0.236442 0.062 Uiso 1 1 calc R U . . .
C4 C 0.5135(4) 0.500000 0.0980(9) 0.0518(9) Uani 1 2 d S T P . .
H4B H 0.547291 0.579886 0.132841 0.062 Uiso 0.5 1 calc R U P . .
H4A H 0.547291 0.420114 0.132841 0.062 Uiso 0.5 1 calc R U P . .
O2 O 0.16(4) 0.500000 0.71(3) 0.0386(17) Uani 0.024(14) 2 d DS TU P A 1
O4 O 0.2145(3) 0.4603(6) 1.0114(8) 0.0386(17) Uani 0.488(7) 1 d D U P A 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
Ni1 O5 2.132(3) 6_564 ?
Ni1 O5 2.132(3) 1_554 ?
Ni1 O3 2.052(8) . ?
Ni1 O1 2.046(3) . ?
Ni1 O1 2.046(3) 6_565 ?
Ni1 N1 2.062(4) . ?
Ni1 C9 2.457(5) 1_554 ?
Ni1 O2 1.9(5) . ?
O5 C9 1.254(3) . ?
O3 C5 1.234(8) . ?
O1 H1A 0.8574 . ?
O1 H1B 0.8570 . ?
N1 C1 1.342(5) . ?
N1 C1 1.342(5) 6_565 ?
C8 C9 1.503(6) . ?
C8 C6 1.396(6) . ?
C8 C7 1.390(6) 5_567 ?
C6 C7 1.391(7) . ?
C6 C5 1.505(7) . ?
C7 H7 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.380(5) . ?
C5 O2 1.28(2) . ?
C5 O4 1.282(9) . ?
C5 O4 1.282(9) 6_565 ?
C3 C2 1.377(7) 6_565 ?
C3 C2 1.377(7) . ?
C3 C4 1.511(8) . ?
C2 H2 0.9300 . ?
C4 C4 1.388(13) 5_665 ?
C4 H4B 0.9700 . ?
C4 H4A 0.9700 . ?
O4 O4 0.775(12) 6_565 ?

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
O5 Ni1 O5 61.33(14) 6_564 1_554 ?
O5 Ni1 C9 30.69(7) 1_554 1_554 ?
O5 Ni1 C9 30.69(7) 6_564 1_554 ?
O3 Ni1 O5 85.0(2) . 6_564 ?
O3 Ni1 O5 85.0(2) . 1_554 ?
O3 Ni1 N1 174.0(3) . . ?
O3 Ni1 C9 82.8(3) . 1_554 ?
O1 Ni1 O5 165.85(11) 6_565 1_554 ?
O1 Ni1 O5 165.85(11) . 6_564 ?
O1 Ni1 O5 104.96(11) 6_565 6_564 ?
O1 Ni1 O5 104.96(11) . 1_554 ?
O1 Ni1 O3 90.51(18) 6_565 . ?
O1 Ni1 O3 90.51(18) . . ?
O1 Ni1 O1 88.45(16) . 6_565 ?
O1 Ni1 N1 93.80(11) . . ?
O1 Ni1 N1 93.80(11) 6_565 . ?
O1 Ni1 C9 135.40(8) 6_565 1_554 ?
O1 Ni1 C9 135.40(8) . 1_554 ?
N1 Ni1 O5 89.83(12) . 1_554 ?
N1 Ni1 O5 89.83(12) . 6_564 ?
N1 Ni1 C9 91.15(15) . 1_554 ?
O2 Ni1 O5 86(10) . 6_564 ?
O2 Ni1 O5 86(10) . 1_554 ?
O2 Ni1 O3 1(10) . . ?
O2 Ni1 O1 90(9) . . ?
O2 Ni1 O1 90(9) . 6_565 ?
O2 Ni1 N1 175(10) . . ?
O2 Ni1 C9 84(10) . 1_554 ?
C9 O5 Ni1 89.2(2) . 1_556 ?
C5 O3 Ni1 126.1(8) . . ?
Ni1 O1 H1A 127.8 . . ?
Ni1 O1 H1B 127.8 . . ?
H1A O1 H1B 104.4 . . ?
C1 N1 Ni1 121.4(2) . . ?
C1 N1 Ni1 121.4(2) 6_565 . ?
C1 N1 C1 117.0(5) 6_565 . ?
C6 C8 C9 123.9(4) . . ?
C7 C8 C9 116.3(4) 5_567 . ?
C7 C8 C6 119.8(4) 5_567 . ?
O5 C9 Ni1 60.1(2) 6_565 1_556 ?
O5 C9 Ni1 60.1(2) . 1_556 ?
O5 C9 O5 120.1(4) 6_565 . ?
O5 C9 C8 119.8(2) 6_565 . ?
O5 C9 C8 119.7(2) . . ?
C8 C9 Ni1 170.0(3) . 1_556 ?
C8 C6 C5 120.6(5) . . ?
C7 C6 C8 119.1(4) . . ?
C7 C6 C5 120.3(5) . . ?
C8 C7 C6 121.1(4) 5_567 . ?
C8 C7 H7 119.4 5_567 . ?
C6 C7 H7 119.4 . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.8(5) . . ?
C2 C1 H1 118.6 . . ?
O3 C5 C6 117.7(7) . . ?
O3 C5 O2 6(10) . . ?
O3 C5 O4 122.6(7) . . ?
O3 C5 O4 122.6(7) . 6_565 ?
O2 C5 C6 124(10) . . ?
O4 C5 C6 116.5(5) . . ?
O4 C5 C6 116.5(5) 6_565 . ?
O4 C5 O4 35.2(5) . 6_565 ?
C2 C3 C2 117.1(6) 6_565 . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 C4 121.5(3) 6_565 . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(6) . . ?
C3 C2 H2 119.9 . . ?
C3 C4 H4B 107.9 . . ?
C3 C4 H4A 107.9 . . ?
C4 C4 C3 117.6(7) 5_665 . ?
C4 C4 H4B 107.9 5_665 . ?
C4 C4 H4A 107.9 5_665 . ?
H4B C4 H4A 107.2 . . ?
C5 O2 Ni1 133(10) . . ?
O4 O4 C5 72.4(3) 6_565 . ?

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
Ni1 O5 C9 O5 -4.5(4) 1_556 . . 6_565 ?
Ni1 O5 C9 C8 168.5(4) 1_556 . . . ?
Ni1 O3 C5 C6 180.000(1) . . . . ?
Ni1 O3 C5 O2 0.00(12) . . . . ?
Ni1 O3 C5 O4 21.0(4) . . . 6_565 ?
Ni1 O3 C5 O4 -21.0(4) . . . . ?
Ni1 N1 C1 C2 -174.3(3) . . . . ?
O3 C5 O2 Ni1 180.00(13) . . . . ?
O3 C5 O4 O4 101.7(4) . . . 6_565 ?
N1 C1 C2 C3 -0.4(7) . . . . ?
C8 C6 C7 C8 0.000(2) . . . 5_567 ?
C8 C6 C5 O3 180.000(2) . . . . ?
C8 C6 C5 O2 180.00(8) . . . . ?
C8 C6 C5 O4 19.8(3) . . . . ?
C8 C6 C5 O4 -19.8(3) . . . 6_565 ?
C9 C8 C6 C7 180.000(2) . . . . ?
C9 C8 C6 C5 0.000(2) . . . . ?
C6 C8 C9 O5 -93.5(4) . . . 6_565 ?
C6 C8 C9 O5 93.5(4) . . . . ?
C6 C5 O2 Ni1 180.00(3) . . . . ?
C6 C5 O4 O4 -99.1(3) . . . 6_565 ?
C7 C8 C9 O5 86.5(4) 5_567 . . 6_565 ?
C7 C8 C9 O5 -86.5(4) 5_567 . . . ?
C7 C8 C6 C7 0.000(2) 5_567 . . . ?
C7 C8 C6 C5 180.000(2) 5_567 . . . ?
C7 C6 C5 O3 0.000(2) . . . . ?
C7 C6 C5 O2 0.00(10) . . . . ?
C7 C6 C5 O4 -160.2(3) . . . . ?
C7 C6 C5 O4 160.2(3) . . . 6_565 ?
C1 N1 C1 C2 -0.3(8) 6_565 . . . ?
C5 C6 C7 C8 180.000(1) . . . 5_567 ?
C2 C3 C2 C1 1.1(9) 6_565 . . . ?
C2 C3 C4 C4 90.6(6) 6_565 . . 5_665 ?
C2 C3 C4 C4 -90.6(6) . . . 5_665 ?
C4 C3 C2 C1 -177.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Co
_database_code_depnum_ccdc_archive 'CCDC 2376993'
_audit_update_record             
;
2024-09-12 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_audit_creation_date             2024-09-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H11 Co N O6'
_chemical_formula_sum            'C11 H11 Co N O6'
_chemical_formula_weight         312.14
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.2564(8)
_cell_length_b                   9.8760(15)
_cell_length_c                   16.8793(19)
_cell_angle_alpha                90
_cell_angle_beta                 100.663(5)
_cell_angle_gamma                90
_cell_volume                     1188.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8268
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      3.55
_shelx_estimated_absorpt_T_max   0.855
_shelx_estimated_absorpt_T_min   0.778
_exptl_absorpt_coefficient_mu    1.466
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13182
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.396
_diffrn_reflns_theta_min         2.400
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2131
_reflns_number_total             2436
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      1.253
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0268P)²+1.3301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0718
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O6_$1-H2B_$2
 2.2 with sigma of 0.02
3.a Rotating group:
 O4(H4A,H4B), O2(H2A,H2B)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C6(H6), C9(H9), C7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.64167(4) 0.49026(3) 0.75548(2) 0.01930(10) Uani 1 1 d . . . . .
O6 O -0.2578(2) 0.59943(16) 0.66106(9) 0.0265(3) Uani 1 1 d . . . . .
O1 O -0.1792(2) 0.38690(15) 0.67765(9) 0.0250(3) Uani 1 1 d . . . . .
O4 O 0.5078(2) 0.63753(16) 0.80948(9) 0.0276(3) Uani 1 1 d . . . . .
H4A H 0.397260 0.648223 0.782839 0.041 Uiso 1 1 d R U . . .
H4B H 0.561200 0.713341 0.805852 0.041 Uiso 1 1 d R U . . .
O3 O 0.3989(2) 0.46475(17) 0.66588(9) 0.0295(4) Uani 1 1 d . . . . .
O2 O 0.5562(2) 0.32325(16) 0.80930(10) 0.0310(4) Uani 1 1 d . . . . .
H2A H 0.643648 0.249794 0.816344 0.047 Uiso 1 1 d R U . . .
H2B H 0.450789 0.276093 0.778962 0.047 Uiso 1 1 d R U . . .
O5 O 0.1905(2) 0.6000(2) 0.70766(10) 0.0393(5) Uani 1 1 d . . . . .
N1 N 0.8949(2) 0.50593(19) 0.84106(11) 0.0241(4) Uani 1 1 d . . . . .
C1 C -0.0793(3) 0.5026(2) 0.56922(12) 0.0194(4) Uani 1 1 d . . . . .
C2 C -0.1742(3) 0.4964(2) 0.64117(12) 0.0196(4) Uani 1 1 d . . . . .
C5 C 0.2448(3) 0.5253(2) 0.65716(12) 0.0217(4) Uani 1 1 d . . . . .
C4 C 0.1154(3) 0.5083(2) 0.57647(12) 0.0198(4) Uani 1 1 d . . . . .
C3 C -0.1924(3) 0.4947(2) 0.49326(13) 0.0221(4) Uani 1 1 d . . . . .
H3 H -0.321940 0.491454 0.488916 0.026 Uiso 1 1 calc R U . . .
C8 C 1.2427(3) 0.5315(3) 0.94522(14) 0.0304(5) Uani 1 1 d . . . . .
C10 C 0.9600(3) 0.6250(3) 0.87081(16) 0.0365(6) Uani 1 1 d . . . . .
H10 H 0.886276 0.701395 0.856582 0.044 Uiso 1 1 calc R U . . .
C6 C 1.0048(3) 0.3991(3) 0.86297(15) 0.0348(6) Uani 1 1 d . . . . .
H6 H 0.963832 0.314552 0.842680 0.042 Uiso 1 1 calc R U . . .
C9 C 1.1297(3) 0.6413(3) 0.92133(16) 0.0389(6) Uani 1 1 d . . . . .
H9 H 1.168728 0.727397 0.939550 0.047 Uiso 1 1 calc R U . . .
C7 C 1.1765(3) 0.4074(3) 0.91426(16) 0.0404(6) Uani 1 1 d . . . . .
H7 H 1.247447 0.329626 0.927963 0.048 Uiso 1 1 calc R U . . .
C11 C 1.4286(4) 0.5523(3) 1.00098(17) 0.0468(7) Uani 1 1 d . . . . .
H11A H 1.479612 0.638529 0.987956 0.056 Uiso 1 1 calc R U . . .
H11B H 1.405858 0.558642 1.055704 0.056 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O6 2.1597(16) 1_655 ?
Co1 O1 2.2559(15) 1_655 ?
Co1 O4 2.0536(15) . ?
Co1 O3 2.1136(14) . ?
Co1 O2 2.0346(16) . ?
Co1 N1 2.1225(17) . ?
O6 C2 1.261(3) . ?
O1 C2 1.249(3) . ?
O4 H4A 0.8506 . ?
O4 H4B 0.8504 . ?
O3 C5 1.253(3) . ?
O2 H2A 0.9569 . ?
O2 H2B 0.9586 . ?
O5 C5 1.245(3) . ?
N1 C10 1.331(3) . ?
N1 C6 1.333(3) . ?
C1 C2 1.504(3) . ?
C1 C4 1.396(3) . ?
C1 C3 1.391(3) . ?
C5 C4 1.514(3) . ?
C4 C3 1.393(3) 3_566 ?
C3 H3 0.9300 . ?
C8 C9 1.374(3) . ?
C8 C7 1.383(4) . ?
C8 C11 1.510(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.372(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(3) . ?
C9 H9 0.9300 . ?
C7 H7 0.9300 . ?
C11 C11 1.467(5) 3_867 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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
O6 Co1 O1 59.11(6) 1_655 1_655 ?
O4 Co1 O6 103.07(6) . 1_655 ?
O4 Co1 O1 161.76(6) . 1_655 ?
O4 Co1 O3 90.12(6) . . ?
O4 Co1 N1 93.86(7) . . ?
O3 Co1 O6 83.22(6) . 1_655 ?
O3 Co1 O1 91.32(6) . 1_655 ?
O3 Co1 N1 176.01(7) . . ?
O2 Co1 O6 155.06(6) . 1_655 ?
O2 Co1 O1 98.59(6) . 1_655 ?
O2 Co1 O4 99.65(7) . . ?
O2 Co1 O3 86.58(7) . . ?
O2 Co1 N1 93.00(7) . . ?
N1 Co1 O6 95.61(7) . 1_655 ?
N1 Co1 O1 84.82(6) . 1_655 ?
C2 O6 Co1 92.21(12) . 1_455 ?
C2 O1 Co1 88.14(12) . 1_455 ?
Co1 O4 H4A 109.3 . . ?
Co1 O4 H4B 109.4 . . ?
H4A O4 H4B 104.5 . . ?
C5 O3 Co1 129.40(14) . . ?
Co1 O2 H2A 114.8 . . ?
Co1 O2 H2B 115.7 . . ?
H2A O2 H2B 98.2 . . ?
C10 N1 Co1 121.55(15) . . ?
C10 N1 C6 116.27(19) . . ?
C6 N1 Co1 121.96(15) . . ?
C4 C1 C2 122.55(18) . . ?
C3 C1 C2 117.50(18) . . ?
C3 C1 C4 119.86(19) . . ?
O6 C2 C1 119.81(18) . . ?
O1 C2 O6 120.54(19) . . ?
O1 C2 C1 119.50(18) . . ?
O3 C5 C4 116.37(18) . . ?
O5 C5 O3 126.24(19) . . ?
O5 C5 C4 117.37(18) . . ?
C1 C4 C5 122.17(19) . . ?
C3 C4 C1 118.84(19) 3_566 . ?
C3 C4 C5 118.90(18) 3_566 . ?
C1 C3 C4 121.30(19) . 3_566 ?
C1 C3 H3 119.4 . . ?
C4 C3 H3 119.4 3_566 . ?
C9 C8 C7 116.2(2) . . ?
C9 C8 C11 119.4(2) . . ?
C7 C8 C11 124.3(2) . . ?
N1 C10 H10 118.2 . . ?
N1 C10 C9 123.6(2) . . ?
C9 C10 H10 118.2 . . ?
N1 C6 H6 118.3 . . ?
N1 C6 C7 123.4(2) . . ?
C7 C6 H6 118.3 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.0(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C11 H11A 108.2 . . ?
C8 C11 H11B 108.2 . . ?
C11 C11 C8 116.3(3) 3_867 . ?
C11 C11 H11A 108.2 3_867 . ?
C11 C11 H11B 108.2 3_867 . ?
H11A C11 H11B 107.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 O6 C2 O1 -0.15(19) 1_455 . . . ?
Co1 O6 C2 C1 175.48(16) 1_455 . . . ?
Co1 O1 C2 O6 0.14(19) 1_455 . . . ?
Co1 O1 C2 C1 -175.50(16) 1_455 . . . ?
Co1 O3 C5 O5 -12.5(4) . . . . ?
Co1 O3 C5 C4 165.80(14) . . . . ?
Co1 N1 C10 C9 -174.8(2) . . . . ?
Co1 N1 C6 C7 175.5(2) . . . . ?
O3 C5 C4 C1 145.0(2) . . . . ?
O3 C5 C4 C3 -38.4(3) . . . 3_566 ?
O5 C5 C4 C1 -36.5(3) . . . . ?
O5 C5 C4 C3 140.1(2) . . . 3_566 ?
N1 C10 C9 C8 -1.0(4) . . . . ?
N1 C6 C7 C8 -0.4(4) . . . . ?
C2 C1 C4 C5 -7.4(3) . . . . ?
C2 C1 C4 C3 176.06(19) . . . 3_566 ?
C2 C1 C3 C4 -176.24(19) . . . 3_566 ?
C4 C1 C2 O6 106.3(2) . . . . ?
C4 C1 C2 O1 -78.0(3) . . . . ?
C4 C1 C3 C4 0.3(3) . . . 3_566 ?
C3 C1 C2 O6 -77.2(3) . . . . ?
C3 C1 C2 O1 98.4(2) . . . . ?
C3 C1 C4 C5 176.24(19) . . . . ?
C3 C1 C4 C3 -0.3(3) . . . 3_566 ?
C10 N1 C6 C7 0.7(4) . . . . ?
C6 N1 C10 C9 0.0(4) . . . . ?
C9 C8 C7 C6 -0.6(4) . . . . ?
C9 C8 C11 C11 -156.5(4) . . . 3_867 ?
C7 C8 C9 C10 1.2(4) . . . . ?
C7 C8 C11 C11 22.3(5) . . . 3_867 ?
C11 C8 C9 C10 -179.9(3) . . . . ?
C11 C8 C7 C6 -179.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
