# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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 
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data_480-13Cu
_database_code_depnum_ccdc_archive 'CCDC 2269625'
_audit_update_record             
;
2023-06-13 deposited with the CCDC.	2023-08-01 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            'C42 H36 Cu2 N4 O14'
_chemical_formula_weight         947.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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                   7.3455(7)
_cell_length_b                   10.4021(9)
_cell_length_c                   12.8273(10)
_cell_angle_alpha                96.431(7)
_cell_angle_beta                 92.558(7)
_cell_angle_gamma                101.886(8)
_cell_volume                     950.75(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6013
_cell_measurement_theta_min      3.476
_cell_measurement_theta_max      70.084

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_F_000             486
_exptl_transmission_factor_min   0.671
_exptl_transmission_factor_max   0.718
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    2.071
_shelx_estimated_absorpt_T_min   0.647
_shelx_estimated_absorpt_T_max   0.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_T_max  0.733
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6013
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.476
_diffrn_reflns_theta_max         70.084
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3503
_reflns_number_gt                2952
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0619P)²+0.7035P] 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_number_reflns         3503
_refine_ls_number_parameters     281
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.1158
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.066
_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
Cu1 Cu 0.56615(6) 0.94895(4) 0.77402(3) 0.02726(16) Uani 1 1 d . . . . .
N1 N 0.4248(3) 0.8426(3) 0.6449(2) 0.0276(5) Uani 1 1 d . . . . .
N2 N 0.5717(4) 0.7680(3) 0.8133(2) 0.0282(5) Uani 1 1 d . . . . .
O1 O 0.6838(3) 1.0269(2) 0.91259(18) 0.0368(5) Uani 1 1 d . . . . .
O2 O 0.6574(4) 1.2364(2) 0.9165(2) 0.0490(7) Uani 1 1 d . . . . .
O3 O 0.8771(3) 0.8991(2) 1.2781(2) 0.0476(7) Uani 1 1 d . . . . .
O4 O 1.1686(3) 1.0123(2) 1.30954(18) 0.0382(6) Uani 1 1 d . . . . .
O5 O 1.0227(4) 1.4642(2) 1.2555(2) 0.0442(6) Uani 1 1 d . U . . .
O6 O 0.4834(3) 1.1095(2) 0.74266(17) 0.0327(5) Uani 1 1 d . . . . .
H1W H 0.3745 1.1042 0.7566 0.039 Uiso 1 1 d R U . . .
H2W H 0.5402 1.1507 0.7997 0.039 Uiso 1 1 d R U . . .
O7 O 0.2081(6) 0.1702(4) 0.5086(3) 0.0936(13) Uani 1 1 d . . . . .
H3W H 0.1842 0.1509 0.5699 0.112 Uiso 1 1 d R U . . .
H4W H 0.1970 0.1238 0.4488 0.112 Uiso 1 1 d R U . . .
C1 C 0.7106(4) 1.1454(3) 0.9556(2) 0.0285(6) Uani 1 1 d . . . . .
C2 C 0.8162(4) 1.1765(3) 1.0618(2) 0.0280(6) Uani 1 1 d . . . . .
C3 C 0.8583(4) 1.0755(3) 1.1151(2) 0.0298(7) Uani 1 1 d . . . . .
H3 H 0.8208 0.9876 1.0853 0.036 Uiso 1 1 calc R U . . .
C4 C 0.9568(4) 1.1065(3) 1.2132(2) 0.0280(6) Uani 1 1 d . . . . .
C5 C 1.0049(4) 0.9976(3) 1.2703(2) 0.0306(7) Uani 1 1 d . . . . .
C6 C 1.0101(4) 1.2369(3) 1.2575(2) 0.0301(7) Uani 1 1 d . . . . .
H6A H 1.0762 1.2576 1.3228 0.036 Uiso 1 1 calc R U . . .
C7 C 0.9652(4) 1.3384(3) 1.2047(3) 0.0309(7) Uani 1 1 d . . . . .
C8 C 0.8687(4) 1.3076(3) 1.1068(3) 0.0308(7) Uani 1 1 d . . . . .
H8 H 0.8392 1.3746 1.0713 0.037 Uiso 1 1 calc R U . . .
C9 C 0.9993(7) 1.5749(4) 1.1965(3) 0.0565(9) Uani 1 1 d . U . . .
H9A H 1.0626 1.5696 1.1328 0.085 Uiso 1 1 calc R U . . .
H9B H 1.0512 1.6576 1.2389 0.085 Uiso 1 1 calc R U . . .
H9C H 0.8690 1.5693 1.1797 0.085 Uiso 1 1 calc R U . . .
C10 C 0.3502(5) 0.8833(3) 0.5619(3) 0.0345(7) Uani 1 1 d . . . . .
H10 H 0.3598 0.9737 0.5608 0.041 Uiso 1 1 calc R U . . .
C11 C 0.2580(5) 0.7963(4) 0.4760(3) 0.0439(9) Uani 1 1 d . . . . .
H11 H 0.2085 0.8285 0.4188 0.053 Uiso 1 1 calc R U . . .
C12 C 0.2413(5) 0.6626(4) 0.4771(3) 0.0462(9) Uani 1 1 d . . . . .
H12 H 0.1788 0.6033 0.4210 0.055 Uiso 1 1 calc R U . . .
C13 C 0.3192(5) 0.6162(3) 0.5633(3) 0.0362(7) Uani 1 1 d . . . . .
C14 C 0.4096(4) 0.7104(3) 0.6452(2) 0.0286(6) Uani 1 1 d . . . . .
C15 C 0.3136(6) 0.4784(4) 0.5725(3) 0.0466(9) Uani 1 1 d . . . . .
H15 H 0.2551 0.4142 0.5182 0.056 Uiso 1 1 calc R U . . .
C16 C 0.3911(6) 0.4410(3) 0.6576(3) 0.0466(9) Uani 1 1 d . . . . .
H16 H 0.3865 0.3515 0.6607 0.056 Uiso 1 1 calc R U . . .
C17 C 0.4805(5) 0.5354(3) 0.7436(3) 0.0369(8) Uani 1 1 d . . . . .
C18 C 0.4912(4) 0.6700(3) 0.7365(2) 0.0288(6) Uani 1 1 d . . . . .
C19 C 0.5587(6) 0.5040(4) 0.8374(3) 0.0449(9) Uani 1 1 d . . . . .
H19 H 0.5565 0.4162 0.8464 0.054 Uiso 1 1 calc R U . . .
C20 C 0.6382(5) 0.6037(4) 0.9152(3) 0.0421(8) Uani 1 1 d . . . . .
H20 H 0.6885 0.5837 0.9777 0.051 Uiso 1 1 calc R U . . .
C21 C 0.6433(5) 0.7345(3) 0.9006(3) 0.0336(7) Uani 1 1 d . . . . .
H21 H 0.6988 0.8010 0.9539 0.040 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
Cu1 O1 1.953(2) . ?
Cu1 O6 1.966(2) . ?
Cu1 N1 2.001(3) . ?
Cu1 N2 2.010(3) . ?
Cu1 O4 2.251(2) 2_777 ?
N1 C10 1.326(4) . ?
N1 C14 1.357(4) . ?
N2 C21 1.328(4) . ?
N2 C18 1.354(4) . ?
O1 C1 1.265(4) . ?
O2 C1 1.241(4) . ?
O3 C5 1.256(4) . ?
O4 C5 1.255(4) . ?
O4 Cu1 2.251(2) 2_777 ?
O5 C7 1.369(4) . ?
O5 C9 1.481(5) . ?
O6 H1W 0.8200 . ?
O6 H2W 0.8500 . ?
O7 H3W 0.8500 . ?
O7 H4W 0.8500 . ?
C1 C2 1.505(4) . ?
C2 C8 1.389(4) . ?
C2 C3 1.394(4) . ?
C3 C4 1.394(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.381(4) . ?
C4 C5 1.508(4) . ?
C6 C7 1.401(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.385(4) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.396(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.399(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(4) . ?
C13 C15 1.444(5) . ?
C14 C18 1.435(4) . ?
C15 C16 1.341(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.428(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.400(4) . ?
C17 C19 1.410(5) . ?
C19 C20 1.371(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.387(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?

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 Cu1 O6 94.70(9) . . ?
O1 Cu1 N1 170.00(10) . . ?
O6 Cu1 N1 91.97(10) . . ?
O1 Cu1 N2 89.43(10) . . ?
O6 Cu1 N2 163.27(10) . . ?
N1 Cu1 N2 82.10(11) . . ?
O1 Cu1 O4 95.06(10) . 2_777 ?
O6 Cu1 O4 96.15(9) . 2_777 ?
N1 Cu1 O4 91.61(10) . 2_777 ?
N2 Cu1 O4 99.62(10) . 2_777 ?
C10 N1 C14 117.8(3) . . ?
C10 N1 Cu1 129.4(2) . . ?
C14 N1 Cu1 112.7(2) . . ?
C21 N2 C18 118.2(3) . . ?
C21 N2 Cu1 129.3(2) . . ?
C18 N2 Cu1 112.5(2) . . ?
C1 O1 Cu1 129.3(2) . . ?
C5 O4 Cu1 127.3(2) . 2_777 ?
C7 O5 C9 117.5(3) . . ?
Cu1 O6 H1W 109.8 . . ?
Cu1 O6 H2W 89.6 . . ?
H1W O6 H2W 100.9 . . ?
H3W O7 H4W 132.7 . . ?
O2 C1 O1 124.9(3) . . ?
O2 C1 C2 118.4(3) . . ?
O1 C1 C2 116.6(3) . . ?
C8 C2 C3 120.4(3) . . ?
C8 C2 C1 118.9(3) . . ?
C3 C2 C1 120.7(3) . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C6 C4 C3 119.8(3) . . ?
C6 C4 C5 120.3(3) . . ?
C3 C4 C5 119.9(3) . . ?
O4 C5 O3 124.0(3) . . ?
O4 C5 C4 118.2(3) . . ?
O3 C5 C4 117.8(3) . . ?
C4 C6 C7 120.5(3) . . ?
C4 C6 H6A 119.8 . . ?
C7 C6 H6A 119.8 . . ?
O5 C7 C8 124.2(3) . . ?
O5 C7 C6 116.1(3) . . ?
C8 C7 C6 119.7(3) . . ?
C7 C8 C2 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C2 C8 H8 120.1 . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 122.8(3) . . ?
N1 C10 H10 118.6 . . ?
C11 C10 H10 118.6 . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 117.3(3) . . ?
C14 C13 C15 118.1(3) . . ?
C12 C13 C15 124.6(3) . . ?
N1 C14 C13 123.4(3) . . ?
N1 C14 C18 116.2(3) . . ?
C13 C14 C18 120.4(3) . . ?
C16 C15 C13 121.3(3) . . ?
C16 C15 H15 119.3 . . ?
C13 C15 H15 119.3 . . ?
C15 C16 C17 121.6(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C19 116.4(3) . . ?
C18 C17 C16 118.6(3) . . ?
C19 C17 C16 125.0(3) . . ?
N2 C18 C17 123.7(3) . . ?
N2 C18 C14 116.3(3) . . ?
C17 C18 C14 120.0(3) . . ?
C20 C19 C17 119.5(3) . . ?
C20 C19 H19 120.2 . . ?
C17 C19 H19 120.2 . . ?
C19 C20 C21 119.9(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
N2 C21 C20 122.3(3) . . ?
N2 C21 H21 118.9 . . ?
C20 C21 H21 118.9 . . ?

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
Cu1 O1 C1 O2 3.1(5) . . . . ?
Cu1 O1 C1 C2 -176.5(2) . . . . ?
O2 C1 C2 C8 -7.2(5) . . . . ?
O1 C1 C2 C8 172.4(3) . . . . ?
O2 C1 C2 C3 171.8(3) . . . . ?
O1 C1 C2 C3 -8.6(5) . . . . ?
C8 C2 C3 C4 -1.3(5) . . . . ?
C1 C2 C3 C4 179.8(3) . . . . ?
C2 C3 C4 C6 0.8(5) . . . . ?
C2 C3 C4 C5 -179.1(3) . . . . ?
Cu1 O4 C5 O3 125.6(3) 2_777 . . . ?
Cu1 O4 C5 C4 -56.3(4) 2_777 . . . ?
C6 C4 C5 O4 -46.8(4) . . . . ?
C3 C4 C5 O4 133.1(3) . . . . ?
C6 C4 C5 O3 131.4(3) . . . . ?
C3 C4 C5 O3 -48.7(4) . . . . ?
C3 C4 C6 C7 0.2(5) . . . . ?
C5 C4 C6 C7 -179.8(3) . . . . ?
C9 O5 C7 C8 -7.4(5) . . . . ?
C9 O5 C7 C6 172.3(3) . . . . ?
C4 C6 C7 O5 179.4(3) . . . . ?
C4 C6 C7 C8 -0.8(5) . . . . ?
O5 C7 C8 C2 -179.9(3) . . . . ?
C6 C7 C8 C2 0.3(5) . . . . ?
C3 C2 C8 C7 0.7(5) . . . . ?
C1 C2 C8 C7 179.7(3) . . . . ?
C14 N1 C10 C11 0.0(5) . . . . ?
Cu1 N1 C10 C11 178.7(3) . . . . ?
N1 C10 C11 C12 0.6(6) . . . . ?
C10 C11 C12 C13 -0.9(6) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C11 C12 C13 C15 -178.8(4) . . . . ?
C10 N1 C14 C13 -0.4(5) . . . . ?
Cu1 N1 C14 C13 -179.3(2) . . . . ?
C10 N1 C14 C18 -179.7(3) . . . . ?
Cu1 N1 C14 C18 1.4(3) . . . . ?
C12 C13 C14 N1 0.1(5) . . . . ?
C15 C13 C14 N1 179.5(3) . . . . ?
C12 C13 C14 C18 179.4(3) . . . . ?
C15 C13 C14 C18 -1.2(5) . . . . ?
C14 C13 C15 C16 0.7(6) . . . . ?
C12 C13 C15 C16 -179.9(4) . . . . ?
C13 C15 C16 C17 0.8(6) . . . . ?
C15 C16 C17 C18 -1.9(6) . . . . ?
C15 C16 C17 C19 177.4(4) . . . . ?
C21 N2 C18 C17 -0.6(5) . . . . ?
Cu1 N2 C18 C17 178.7(2) . . . . ?
C21 N2 C18 C14 177.8(3) . . . . ?
Cu1 N2 C18 C14 -2.9(3) . . . . ?
C19 C17 C18 N2 0.3(5) . . . . ?
C16 C17 C18 N2 179.7(3) . . . . ?
C19 C17 C18 C14 -178.0(3) . . . . ?
C16 C17 C18 C14 1.4(5) . . . . ?
N1 C14 C18 N2 1.0(4) . . . . ?
C13 C14 C18 N2 -178.3(3) . . . . ?
N1 C14 C18 C17 179.5(3) . . . . ?
C13 C14 C18 C17 0.1(5) . . . . ?
C18 C17 C19 C20 0.4(5) . . . . ?
C16 C17 C19 C20 -178.9(4) . . . . ?
C17 C19 C20 C21 -0.9(6) . . . . ?
C18 N2 C21 C20 0.1(5) . . . . ?
Cu1 N2 C21 C20 -179.1(2) . . . . ?
C19 C20 C21 N2 0.7(5) . . . . ?

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
C21 H21 O1 0.93 2.49 2.980(4) 113.2 .
C11 H11 O4 0.93 2.55 3.406(4) 153.2 1_454
C10 H10 O7 0.93 2.65 3.484(5) 148.9 1_565
C10 H10 O6 0.93 2.61 3.081(4) 112.1 .
O7 H4W O4 0.85 2.00 2.846(4) 179.0 1_444
O7 H3W O3 0.85 2.12 2.967(5) 179.4 2_667
O6 H2W O2 0.85 1.75 2.596(3) 179.6 .
O6 H2W O1 0.85 2.39 2.883(3) 117.5 .
O6 H1W O3 0.82 1.87 2.632(3) 153.2 2_677
C21 H21 O1 0.93 2.49 2.980(4) 113.2 .
C11 H11 O4 0.93 2.55 3.406(4) 153.2 1_454
C10 H10 O7 0.93 2.65 3.484(5) 148.9 1_565
C10 H10 O6 0.93 2.61 3.081(4) 112.1 .
O7 H4W O4 0.85 2.00 2.846(4) 179.0 1_444
O7 H3W O3 0.85 2.12 2.967(5) 179.4 2_667
O6 H2W O2 0.85 1.75 2.596(3) 179.6 .
O6 H2W O1 0.85 2.39 2.883(3) 117.5 .
O6 H1W O3 0.82 1.87 2.632(3) 153.2 2_677
O6 H1W O3 0.82 1.87 2.632(3) 153.2 2_677
O6 H2W O1 0.85 2.39 2.883(3) 117.5 .
O6 H2W O2 0.85 1.75 2.596(3) 179.6 .
O7 H3W O3 0.85 2.12 2.967(5) 179.4 2_667
O7 H4W O4 0.85 2.00 2.846(4) 179.0 1_444
C9 H9A O2 0.96 2.72 3.353(6) 124.0 2_787
C10 H10 O6 0.93 2.61 3.081(4) 112.1 .
C11 H11 O4 0.93 2.55 3.406(4) 153.2 1_454
C21 H21 O1 0.93 2.49 2.980(4) 113.2 .
O6 H1W O3 0.82 1.87 2.632(3) 153.2 2_677
O6 H2W O1 0.85 2.39 2.883(3) 117.5 .
O6 H2W O2 0.85 1.75 2.596(3) 179.6 .
O7 H3W O3 0.85 2.12 2.967(5) 179.4 2_667
O7 H4W O4 0.85 2.00 2.846(4) 179.0 1_444
C10 H10 O6 0.93 2.61 3.081(4) 112.1 .
C10 H10 O7 0.93 2.65 3.484(5) 148.9 1_565
C11 H11 O4 0.93 2.55 3.406(4) 153.2 1_454
C21 H21 O1 0.93 2.49 2.980(4) 113.2 .
O6 H1W O3 0.82 1.87 2.632(3) 153.2 2_677
O6 H2W O1 0.85 2.39 2.883(3) 117.5 .
O6 H2W O2 0.85 1.75 2.596(3) 179.6 .
O7 H3W O3 0.85 2.12 2.967(5) 179.4 2_667
O7 H4W O4 0.85 2.00 2.846(4) 179.0 1_444
C9 H9A O2 0.96 2.72 3.353(6) 124.0 2_787
C10 H10 O6 0.93 2.61 3.081(4) 112.1 .
C11 H11 O4 0.93 2.55 3.406(4) 153.2 1_454
C21 H21 O1 0.93 2.49 2.980(4) 113.2 .

_refine_diff_density_max         1.340
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_480-20Co
_database_code_depnum_ccdc_archive 'CCDC 2269627'
_audit_update_record             
;
2023-06-13 deposited with the CCDC.	2023-08-01 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            'C19 H18 Co N2 O7'
_chemical_formula_weight         445.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8603(3)
_cell_length_b                   17.4505(5)
_cell_length_c                   12.4228(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.718(3)
_cell_angle_gamma                90
_cell_volume                     1903.37(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6636
_cell_measurement_theta_min      4.395
_cell_measurement_theta_max      66.584

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_F_000             916
_exptl_transmission_factor_min   0.274
_exptl_transmission_factor_max   0.326
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    7.480
_shelx_estimated_absorpt_T_min   0.303
_shelx_estimated_absorpt_T_max   0.400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.303
_exptl_absorpt_correction_T_max  0.400
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6636
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.395
_diffrn_reflns_theta_max         66.584
_diffrn_reflns_theta_full        66.584
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3367
_reflns_number_gt                2795
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0500P)²+0.3661P] 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_number_reflns         3367
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.16181(5) 0.15177(2) 0.91985(3) 0.02907(13) Uani 1 1 d . . . . .
N1 N 0.3625(3) 0.17031(13) 0.84678(17) 0.0358(5) Uani 1 1 d . . . . .
N2 N 0.3347(2) 0.10248(12) 1.03075(17) 0.0321(5) Uani 1 1 d . . . . .
O1 O 0.2124(3) 0.26872(12) 1.00873(17) 0.0558(6) Uani 1 1 d . . . . .
O2 O 0.0648(3) 0.25894(11) 0.85654(16) 0.0520(6) Uani 1 1 d . . . . .
O3 O -0.0612(3) 0.60452(11) 0.72014(15) 0.0446(5) Uani 1 1 d . . . . .
O4 O -0.0678(2) 0.49556(11) 0.62954(15) 0.0424(5) Uani 1 1 d . . . . .
O5 O 0.3145(3) 0.54774(13) 1.06075(17) 0.0706(8) Uani 1 1 d . . . . .
O6 O -0.0173(2) 0.13265(11) 1.01182(15) 0.0401(5) Uani 1 1 d . . . . .
H1W H -0.0071 0.0880 1.0428 0.048 Uiso 1 1 d R U . . .
H2W H 0.0038 0.1249 0.9479 0.048 Uiso 1 1 d R U . . .
O7 O 0.9459(3) 0.25124(13) 0.14335(18) 0.0592(6) Uani 1 1 d . . . . .
H3W H 0.9846 0.2209 0.1018 0.071 Uiso 1 1 d R U . . .
H4W H 0.9810 0.2484 0.2086 0.071 Uiso 1 1 d R U . . .
C1 C 0.1376(3) 0.29931(16) 0.9285(2) 0.0388(7) Uani 1 1 d . . . . .
C2 C 0.1372(3) 0.38499(15) 0.9157(2) 0.0346(6) Uani 1 1 d . . . . .
C3 C 0.0549(3) 0.41888(15) 0.8250(2) 0.0326(6) Uani 1 1 d . . . . .
H3 H -0.0020 0.3886 0.7729 0.039 Uiso 1 1 calc R U . . .
C4 C 0.0574(3) 0.49750(15) 0.81225(19) 0.0309(6) Uani 1 1 d . . . . .
C5 C -0.0305(3) 0.53443(15) 0.7132(2) 0.0331(6) Uani 1 1 d . . . . .
C6 C 0.1419(3) 0.54286(16) 0.8909(2) 0.0392(7) Uani 1 1 d . . . . .
H6 H 0.1421 0.5959 0.8833 0.047 Uiso 1 1 calc R U . . .
C7 C 0.2256(4) 0.50873(17) 0.9804(2) 0.0450(7) Uani 1 1 d . . . . .
C8 C 0.2217(4) 0.42970(16) 0.9928(2) 0.0439(7) Uani 1 1 d . . . . .
H8 H 0.2765 0.4069 1.0536 0.053 Uiso 1 1 calc R U . . .
C9 C 0.3273(6) 0.6290(2) 1.0505(3) 0.0919(17) Uani 1 1 d . . . . .
H9B H 0.3665 0.6409 0.9840 0.138 Uiso 1 1 calc R U . . .
H9A H 0.3953 0.6487 1.1108 0.138 Uiso 1 1 calc R U . . .
H9C H 0.2288 0.6521 1.0496 0.138 Uiso 1 1 calc R U . . .
C10 C 0.3666(4) 0.20487(19) 0.7501(2) 0.0483(8) Uani 1 1 d . . . . .
H10 H 0.2753 0.2199 0.7098 0.058 Uiso 1 1 calc R U . . .
C11 C 0.5004(4) 0.2187(2) 0.7091(3) 0.0565(9) Uani 1 1 d . . . . .
H11 H 0.4995 0.2425 0.6420 0.068 Uiso 1 1 calc R U . . .
C12 C 0.6352(4) 0.1968(2) 0.7681(3) 0.0589(9) Uani 1 1 d . . . . .
H12 H 0.7270 0.2057 0.7418 0.071 Uiso 1 1 calc R U . . .
C13 C 0.6328(3) 0.16144(19) 0.8672(3) 0.0497(8) Uani 1 1 d . . . . .
H13 H 0.7232 0.1461 0.9084 0.060 Uiso 1 1 calc R U . . .
C14 C 0.4945(3) 0.14907(15) 0.9045(2) 0.0347(6) Uani 1 1 d . . . . .
C15 C 0.4789(3) 0.11053(15) 1.0092(2) 0.0327(6) Uani 1 1 d . . . . .
C16 C 0.6011(3) 0.08336(19) 1.0798(2) 0.0459(7) Uani 1 1 d . . . . .
H16 H 0.6996 0.0882 1.0625 0.055 Uiso 1 1 calc R U . . .
C17 C 0.5766(4) 0.0492(2) 1.1756(2) 0.0520(8) Uani 1 1 d . . . . .
H17 H 0.6582 0.0312 1.2240 0.062 Uiso 1 1 calc R U . . .
C18 C 0.4304(4) 0.0420(2) 1.1989(2) 0.0521(8) Uani 1 1 d . . . . .
H18 H 0.4108 0.0197 1.2636 0.063 Uiso 1 1 calc R U . . .
C19 C 0.3127(4) 0.06870(18) 1.1240(2) 0.0438(7) Uani 1 1 d . . . . .
H19 H 0.2134 0.0629 1.1392 0.053 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 O3 2.0205(19) 2_546 ?
Co1 N2 2.102(2) . ?
Co1 O6 2.1028(19) . ?
Co1 N1 2.127(2) . ?
Co1 O2 2.162(2) . ?
Co1 O1 2.335(2) . ?
Co1 H2W 1.5596 . ?
N1 C14 1.339(4) . ?
N1 C10 1.348(3) . ?
N2 C19 1.337(3) . ?
N2 C15 1.348(3) . ?
O1 C1 1.242(3) . ?
O2 C1 1.247(3) . ?
O3 C5 1.258(3) . ?
O3 Co1 2.0206(19) 2_556 ?
O4 C5 1.248(3) . ?
O5 C7 1.367(3) . ?
O5 C9 1.430(4) . ?
O6 H1W 0.8693 . ?
O6 H2W 0.8500 . ?
O7 H3W 0.8436 . ?
O7 H4W 0.8293 . ?
C1 C2 1.504(4) . ?
C2 C8 1.377(4) . ?
C2 C3 1.389(4) . ?
C3 C4 1.382(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.395(4) . ?
C4 C5 1.509(3) . ?
C6 C7 1.385(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.389(4) . ?
C8 H8 0.9300 . ?
C9 H9B 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.374(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.486(4) . ?
C15 C16 1.383(4) . ?
C16 C17 1.374(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

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
O3 Co1 N2 126.57(9) 2_546 . ?
O3 Co1 O6 97.18(8) 2_546 . ?
N2 Co1 O6 96.64(8) . . ?
O3 Co1 N1 89.57(9) 2_546 . ?
N2 Co1 N1 76.38(9) . . ?
O6 Co1 N1 172.36(8) . . ?
O3 Co1 O2 86.09(8) 2_546 . ?
N2 Co1 O2 144.26(9) . . ?
O6 Co1 O2 92.45(8) . . ?
N1 Co1 O2 91.58(9) . . ?
O3 Co1 O1 142.95(8) 2_546 . ?
N2 Co1 O1 88.33(8) . . ?
O6 Co1 O1 89.58(8) . . ?
N1 Co1 O1 87.16(9) . . ?
O2 Co1 O1 57.15(8) . . ?
O3 Co1 H2W 76.4 2_546 . ?
N2 Co1 H2W 109.1 . . ?
O6 Co1 H2W 20.8 . . ?
N1 Co1 H2W 165.5 . . ?
O2 Co1 H2W 90.9 . . ?
O1 Co1 H2W 106.1 . . ?
C14 N1 C10 118.4(3) . . ?
C14 N1 Co1 116.70(17) . . ?
C10 N1 Co1 124.9(2) . . ?
C19 N2 C15 118.1(2) . . ?
C19 N2 Co1 124.8(2) . . ?
C15 N2 Co1 117.00(17) . . ?
C1 O1 Co1 87.02(17) . . ?
C1 O2 Co1 94.94(18) . . ?
C5 O3 Co1 114.34(18) . 2_556 ?
C7 O5 C9 118.3(3) . . ?
Co1 O6 H1W 110.0 . . ?
Co1 O6 H2W 40.7 . . ?
H1W O6 H2W 104.4 . . ?
H3W O7 H4W 115.4 . . ?
O1 C1 O2 120.1(3) . . ?
O1 C1 C2 120.4(3) . . ?
O2 C1 C2 119.5(3) . . ?
C8 C2 C3 120.0(3) . . ?
C8 C2 C1 119.8(2) . . ?
C3 C2 C1 120.2(2) . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C6 119.9(2) . . ?
C3 C4 C5 120.2(2) . . ?
C6 C4 C5 119.9(2) . . ?
O4 C5 O3 123.3(3) . . ?
O4 C5 C4 119.8(2) . . ?
O3 C5 C4 116.9(2) . . ?
C7 C6 C4 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
C4 C6 H6 120.1 . . ?
O5 C7 C6 124.4(3) . . ?
O5 C7 C8 115.7(3) . . ?
C6 C7 C8 119.9(3) . . ?
C2 C8 C7 120.3(3) . . ?
C2 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
O5 C9 H9B 109.5 . . ?
O5 C9 H9A 109.5 . . ?
H9B C9 H9A 109.5 . . ?
O5 C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
N1 C10 C11 122.4(3) . . ?
N1 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C12 C11 C10 119.1(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 119.1(3) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
N1 C14 C13 121.7(3) . . ?
N1 C14 C15 114.6(2) . . ?
C13 C14 C15 123.6(3) . . ?
N2 C15 C16 121.4(2) . . ?
N2 C15 C14 115.0(2) . . ?
C16 C15 C14 123.6(3) . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 119.0(3) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 118.5(3) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
N2 C19 C18 123.1(3) . . ?
N2 C19 H19 118.4 . . ?
C18 C19 H19 118.4 . . ?

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 O1 C1 O2 8.6(3) . . . . ?
Co1 O1 C1 C2 -169.8(2) . . . . ?
Co1 O2 C1 O1 -9.3(3) . . . . ?
Co1 O2 C1 C2 169.1(2) . . . . ?
O1 C1 C2 C8 0.7(4) . . . . ?
O2 C1 C2 C8 -177.7(3) . . . . ?
O1 C1 C2 C3 179.2(3) . . . . ?
O2 C1 C2 C3 0.8(4) . . . . ?
C8 C2 C3 C4 -0.1(4) . . . . ?
C1 C2 C3 C4 -178.6(2) . . . . ?
C2 C3 C4 C6 -0.4(4) . . . . ?
C2 C3 C4 C5 179.3(2) . . . . ?
Co1 O3 C5 O4 -4.7(4) 2_556 . . . ?
Co1 O3 C5 C4 174.69(17) 2_556 . . . ?
C3 C4 C5 O4 -20.9(4) . . . . ?
C6 C4 C5 O4 158.8(3) . . . . ?
C3 C4 C5 O3 159.7(2) . . . . ?
C6 C4 C5 O3 -20.6(4) . . . . ?
C3 C4 C6 C7 1.4(4) . . . . ?
C5 C4 C6 C7 -178.4(3) . . . . ?
C9 O5 C7 C6 -2.5(5) . . . . ?
C9 O5 C7 C8 177.8(3) . . . . ?
C4 C6 C7 O5 178.6(3) . . . . ?
C4 C6 C7 C8 -1.7(5) . . . . ?
C3 C2 C8 C7 -0.2(4) . . . . ?
C1 C2 C8 C7 178.2(3) . . . . ?
O5 C7 C8 C2 -179.2(3) . . . . ?
C6 C7 C8 C2 1.1(5) . . . . ?
C14 N1 C10 C11 0.2(5) . . . . ?
Co1 N1 C10 C11 176.8(2) . . . . ?
N1 C10 C11 C12 -0.2(5) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C10 N1 C14 C13 -0.3(4) . . . . ?
Co1 N1 C14 C13 -177.1(2) . . . . ?
C10 N1 C14 C15 -179.2(2) . . . . ?
Co1 N1 C14 C15 3.9(3) . . . . ?
C12 C13 C14 N1 0.3(5) . . . . ?
C12 C13 C14 C15 179.1(3) . . . . ?
C19 N2 C15 C16 1.4(4) . . . . ?
Co1 N2 C15 C16 176.9(2) . . . . ?
C19 N2 C15 C14 -179.6(2) . . . . ?
Co1 N2 C15 C14 -4.1(3) . . . . ?
N1 C14 C15 N2 0.0(3) . . . . ?
C13 C14 C15 N2 -178.9(3) . . . . ?
N1 C14 C15 C16 179.1(3) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
N2 C15 C16 C17 -1.8(5) . . . . ?
C14 C15 C16 C17 179.2(3) . . . . ?
C15 C16 C17 C18 0.6(5) . . . . ?
C16 C17 C18 C19 0.8(5) . . . . ?
C15 N2 C19 C18 0.2(4) . . . . ?
Co1 N2 C19 C18 -175.0(3) . . . . ?
C17 C18 C19 N2 -1.3(5) . . . . ?

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
C16 H16 O4 0.93 2.57 3.224(4) 127.6 4_666
C13 H13 O6 0.93 2.49 3.405(4) 168.0 1_655
C10 H10 O1 0.93 2.49 3.158(4) 128.6 4_565
O7 H4W O2 0.83 1.89 2.721(3) 178.9 4_665
O7 H3W O6 0.84 1.90 2.684(3) 153.6 1_654
O7 H3W O1 0.84 2.60 3.086(3) 118.4 1_654
O6 H1W O4 0.87 1.93 2.742(3) 154.7 4_566
O6 H1W O4 0.87 1.93 2.742(3) 154.7 4_566
O7 H3W O1 0.84 2.60 3.086(3) 118.4 1_654
O7 H3W O6 0.84 1.90 2.684(3) 153.6 1_654
O7 H4W O2 0.83 1.89 2.721(3) 178.9 4_665
C10 H10 O1 0.93 2.49 3.158(4) 128.6 4_565
C13 H13 O6 0.93 2.49 3.405(4) 168.0 1_655
C16 H16 O4 0.93 2.57 3.224(4) 127.6 4_666

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_480-16Mn
_database_code_depnum_ccdc_archive 'CCDC 2269626'
_audit_update_record             
;
2023-06-13 deposited with the CCDC.	2023-08-01 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            'C42 H28 Mn2 N4 O10'
_chemical_formula_weight         858.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   38.823(4)
_cell_length_b                   10.4967(8)
_cell_length_c                   18.7612(12)
_cell_angle_alpha                90
_cell_angle_beta                 105.531(8)
_cell_angle_gamma                90
_cell_volume                     7366.3(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13886
_cell_measurement_theta_min      4.375
_cell_measurement_theta_max      70.009

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             3504
_exptl_transmission_factor_min   0.282
_exptl_transmission_factor_max   0.330
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    6.161
_shelx_estimated_absorpt_T_min   0.332
_shelx_estimated_absorpt_T_max   0.403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.332
_exptl_absorpt_correction_T_max  0.403
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13886
_diffrn_reflns_av_unetI/netI     0.1224
_diffrn_reflns_av_R_equivalents  0.0933
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.375
_diffrn_reflns_theta_max         70.009
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6861
_reflns_number_gt                3204
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1119P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6861
_refine_ls_number_parameters     526
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1554
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.2689
_refine_ls_wR_factor_gt          0.1956
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_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
Mn1 Mn 0.91243(3) 1.18571(11) 0.23401(5) 0.0488(4) Uani 1 1 d . . . . .
Mn2 Mn 0.85066(3) 0.81464(11) 0.52294(6) 0.0519(4) Uani 1 1 d . . . . .
N1 N 0.94070(15) 1.3457(5) 0.1898(3) 0.0472(14) Uani 1 1 d . . . . .
N2 N 0.88359(18) 1.3706(6) 0.2453(3) 0.0629(17) Uani 1 1 d . . . . .
N3 N 0.82166(18) 0.6375(6) 0.5508(3) 0.0625(18) Uani 1 1 d . . . . .
N4 N 0.87896(18) 0.6413(7) 0.4943(4) 0.0654(18) Uani 1 1 d . . . . .
O1 O 0.85888(15) 1.1269(5) 0.1837(3) 0.0722(17) Uani 1 1 d . . . . .
O2 O 0.82371(14) 1.0601(5) 0.0777(2) 0.0646(15) Uani 1 1 d . . . . .
O3 O 0.84987(16) 0.9205(6) 0.4195(3) 0.0799(18) Uani 1 1 d . . . . .
O4 O 0.80562(16) 0.7913(6) 0.4150(3) 0.0835(19) Uani 1 1 d . . . . .
O5 O 0.73571(15) 0.7759(6) 0.1444(3) 0.086(2) Uani 1 1 d . . . . .
O6 O 0.95795(15) 1.2018(6) 0.3404(3) 0.0746(17) Uani 1 1 d . . . . .
O7 O 0.90901(15) 1.1051(6) 0.3416(3) 0.0808(19) Uani 1 1 d . . . . .
O8 O 0.90320(15) 0.8754(5) 0.5734(3) 0.0627(14) Uani 1 1 d . . . . .
O9 O 0.93720(15) 0.9483(5) 0.6800(2) 0.0616(14) Uani 1 1 d . . . . .
O10 O 1.03219(15) 1.2060(6) 0.5998(3) 0.0756(17) Uani 1 1 d . . . . .
C1 C 0.8350(2) 1.0575(7) 0.1474(4) 0.0559(19) Uani 1 1 d . . . . .
C2 C 0.81503(18) 0.9746(7) 0.1888(3) 0.0464(16) Uani 1 1 d . . . . .
C3 C 0.82805(19) 0.9586(6) 0.2646(4) 0.0498(17) Uani 1 1 d . . . . .
H3 H 0.8491 0.9983 0.2903 0.060 Uiso 1 1 calc R U . . .
C4 C 0.80919(19) 0.8821(6) 0.3018(3) 0.0474(17) Uani 1 1 d . . . . .
C5 C 0.8222(2) 0.8627(7) 0.3841(4) 0.0555(19) Uani 1 1 d . . . . .
C6 C 0.77798(19) 0.8210(7) 0.2636(4) 0.0539(18) Uani 1 1 d . . . . .
H6 H 0.7653 0.7709 0.2888 0.065 Uiso 1 1 calc R U . . .
C7 C 0.7659(2) 0.8353(8) 0.1877(4) 0.062(2) Uani 1 1 d . . . . .
C8 C 0.7841(2) 0.9126(7) 0.1506(4) 0.059(2) Uani 1 1 d . . . . .
H8 H 0.7756 0.9230 0.0997 0.071 Uiso 1 1 calc R U . . .
C9 C 0.7190(2) 0.6803(8) 0.1798(5) 0.087(3) Uani 1 1 d . . . . .
H9C H 0.6976 0.6502 0.1454 0.131 Uiso 1 1 calc R U . . .
H9B H 0.7132 0.7170 0.2220 0.131 Uiso 1 1 calc R U . . .
H9A H 0.7352 0.6104 0.1955 0.131 Uiso 1 1 calc R U . . .
C10 C 0.9394(2) 1.1435(7) 0.3742(4) 0.0501(17) Uani 1 1 d . . . . .
C11 C 0.95376(19) 1.1192(6) 0.4563(3) 0.0489(17) Uani 1 1 d . . . . .
C12 C 0.93440(18) 1.0441(6) 0.4929(3) 0.0439(16) Uani 1 1 d . . . . .
H12 H 0.9127 1.0078 0.4676 0.053 Uiso 1 1 calc R U . . .
C13 C 0.94860(19) 1.0252(6) 0.5687(3) 0.0473(17) Uani 1 1 d . . . . .
C14 C 0.9282(2) 0.9452(7) 0.6103(4) 0.0550(19) Uani 1 1 d . . . . .
C15 C 0.9810(2) 1.0761(6) 0.6061(4) 0.0512(18) Uani 1 1 d . . . . .
H15 H 0.9901 1.0607 0.6565 0.061 Uiso 1 1 calc R U . . .
C16 C 1.00004(19) 1.1500(7) 0.5693(4) 0.0513(18) Uani 1 1 d . . . . .
C17 C 0.9866(2) 1.1707(6) 0.4928(4) 0.0513(18) Uani 1 1 d . . . . .
H17 H 0.9995 1.2183 0.4671 0.062 Uiso 1 1 calc R U . . .
C18 C 1.0483(3) 1.1877(10) 0.6762(5) 0.115(4) Uani 1 1 d . . . . .
H18A H 1.0354 1.2353 0.7044 0.173 Uiso 1 1 calc R U . . .
H18B H 1.0726 1.2166 0.6882 0.173 Uiso 1 1 calc R U . . .
H18C H 1.0478 1.0988 0.6880 0.173 Uiso 1 1 calc R U . . .
C19 C 0.9697(2) 1.3342(8) 0.1672(4) 0.067(2) Uani 1 1 d . . . . .
H19 H 0.9806 1.2549 0.1693 0.080 Uiso 1 1 calc R U . . .
C20 C 0.9845(3) 1.4376(10) 0.1404(5) 0.090(3) Uani 1 1 d . . . . .
H20 H 1.0057 1.4265 0.1270 0.107 Uiso 1 1 calc R U . . .
C21 C 0.9695(3) 1.5523(10) 0.1332(6) 0.098(4) Uani 1 1 d . . . . .
H21 H 0.9793 1.6202 0.1137 0.117 Uiso 1 1 calc R U . . .
C22 C 0.9386(3) 1.5668(8) 0.1558(5) 0.077(3) Uani 1 1 d . . . . .
C23 C 0.9255(2) 1.4625(7) 0.1862(4) 0.0526(18) Uani 1 1 d . . . . .
C24 C 0.9193(3) 1.6855(9) 0.1497(6) 0.104(4) Uani 1 1 d . . . . .
H24 H 0.9272 1.7549 0.1277 0.125 Uiso 1 1 calc R U . . .
C25 C 0.8903(3) 1.6988(10) 0.1749(6) 0.099(4) Uani 1 1 d . . . . .
H25 H 0.8785 1.7767 0.1705 0.119 Uiso 1 1 calc R U . . .
C26 C 0.8776(3) 1.5938(9) 0.2085(5) 0.076(3) Uani 1 1 d . . . . .
C27 C 0.8945(2) 1.4733(7) 0.2144(4) 0.063(2) Uani 1 1 d . . . . .
C28 C 0.8488(3) 1.6017(12) 0.2373(7) 0.110(4) Uani 1 1 d . . . . .
H28 H 0.8369 1.6792 0.2353 0.132 Uiso 1 1 calc R U . . .
C29 C 0.8370(3) 1.5009(12) 0.2682(7) 0.110(4) Uani 1 1 d . . . . .
H29 H 0.8175 1.5091 0.2877 0.132 Uiso 1 1 calc R U . . .
C30 C 0.8548(3) 1.3804(10) 0.2707(6) 0.090(3) Uani 1 1 d . . . . .
H30 H 0.8463 1.3093 0.2902 0.107 Uiso 1 1 calc R U . . .
C31 C 0.7915(3) 0.6374(10) 0.5714(5) 0.087(3) Uani 1 1 d . . . . .
H31 H 0.7835 0.7145 0.5853 0.104 Uiso 1 1 calc R U . . .
C32 C 0.7710(3) 0.5276(11) 0.5734(5) 0.095(3) Uani 1 1 d . . . . .
H32 H 0.7501 0.5327 0.5886 0.113 Uiso 1 1 calc R U . . .
C33 C 0.7821(3) 0.4142(11) 0.5529(5) 0.096(3) Uani 1 1 d . . . . .
H33 H 0.7691 0.3404 0.5550 0.115 Uiso 1 1 calc R U . . .
C34 C 0.8135(3) 0.4088(9) 0.5282(5) 0.085(3) Uani 1 1 d . . . . .
C35 C 0.8316(3) 0.5233(8) 0.5261(4) 0.070(2) Uani 1 1 d . . . . .
C36 C 0.8273(3) 0.2948(10) 0.5028(6) 0.099(4) Uani 1 1 d . . . . .
H36 H 0.8156 0.2179 0.5036 0.119 Uiso 1 1 calc R U . . .
C37 C 0.8563(3) 0.2971(10) 0.4782(6) 0.111(5) Uani 1 1 d . . . . .
H37 H 0.8649 0.2206 0.4646 0.134 Uiso 1 1 calc R U . . .
C38 C 0.8752(3) 0.4125(9) 0.4717(5) 0.087(3) Uani 1 1 d . . . . .
C39 C 0.8630(2) 0.5269(8) 0.4974(4) 0.066(2) Uani 1 1 d . . . . .
C40 C 0.9056(3) 0.4239(13) 0.4447(6) 0.114(5) Uani 1 1 d . . . . .
H40 H 0.9154 0.3518 0.4290 0.136 Uiso 1 1 calc R U . . .
C41 C 0.9206(3) 0.5386(12) 0.4416(7) 0.111(4) Uani 1 1 d . . . . .
H41 H 0.9401 0.5462 0.4219 0.133 Uiso 1 1 calc R U . . .
C42 C 0.9071(2) 0.6441(10) 0.4675(5) 0.087(3) Uani 1 1 d . . . . .
H42 H 0.9183 0.7219 0.4661 0.105 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
Mn1 O9 2.110(5) 6_575 ?
Mn1 O1 2.132(5) . ?
Mn1 O7 2.226(5) . ?
Mn1 N2 2.278(7) . ?
Mn1 N1 2.280(6) . ?
Mn1 O6 2.291(5) . ?
Mn2 O8 2.105(5) . ?
Mn2 O2 2.111(5) 6_576 ?
Mn2 O3 2.230(5) . ?
Mn2 N4 2.263(7) . ?
Mn2 N3 2.304(7) . ?
Mn2 O4 2.308(6) . ?
N1 C19 1.312(9) . ?
N1 C23 1.354(9) . ?
N2 C30 1.330(10) . ?
N2 C27 1.346(10) . ?
N3 C31 1.327(10) . ?
N3 C35 1.377(10) . ?
N4 C42 1.319(10) . ?
N4 C39 1.360(10) . ?
O1 C1 1.232(8) . ?
O2 C1 1.263(8) . ?
O2 Mn2 2.110(5) 6_575 ?
O3 C5 1.257(9) . ?
O4 C5 1.229(9) . ?
O5 C7 1.383(8) . ?
O5 C9 1.448(9) . ?
O6 C10 1.239(8) . ?
O7 C10 1.242(8) . ?
O8 C14 1.263(8) . ?
O9 C14 1.260(8) . ?
O9 Mn1 2.110(5) 6_576 ?
O10 C16 1.359(8) . ?
O10 C18 1.416(9) . ?
C1 C2 1.510(9) . ?
C2 C8 1.384(9) . ?
C2 C3 1.386(8) . ?
C3 C4 1.394(9) . ?
C3 H3 0.9300 . ?
C4 C6 1.388(9) . ?
C4 C5 1.505(9) . ?
C6 C7 1.383(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(9) . ?
C8 H8 0.9300 . ?
C9 H9C 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9A 0.9600 . ?
C10 C11 1.513(9) . ?
C11 C17 1.385(9) . ?
C11 C12 1.390(9) . ?
C12 C13 1.396(8) . ?
C12 H12 0.9300 . ?
C13 C15 1.374(9) . ?
C13 C14 1.508(9) . ?
C15 C16 1.377(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.407(9) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.384(11) . ?
C19 H19 0.9300 . ?
C20 C21 1.329(13) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(13) . ?
C21 H21 0.9300 . ?
C22 C23 1.393(11) . ?
C22 C24 1.442(12) . ?
C23 C27 1.444(11) . ?
C24 C25 1.341(13) . ?
C24 H24 0.9300 . ?
C25 C26 1.421(13) . ?
C25 H25 0.9300 . ?
C26 C28 1.370(14) . ?
C26 C27 1.415(11) . ?
C28 C29 1.343(15) . ?
C28 H28 0.9300 . ?
C29 C30 1.436(14) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C32 1.409(12) . ?
C31 H31 0.9300 . ?
C32 C33 1.356(13) . ?
C32 H32 0.9300 . ?
C33 C34 1.417(13) . ?
C33 H33 0.9300 . ?
C34 C35 1.398(12) . ?
C34 C36 1.443(14) . ?
C35 C39 1.460(12) . ?
C36 C37 1.328(14) . ?
C36 H36 0.9300 . ?
C37 C38 1.436(14) . ?
C37 H37 0.9300 . ?
C38 C40 1.411(14) . ?
C38 C39 1.421(11) . ?
C40 C41 1.344(16) . ?
C40 H40 0.9300 . ?
C41 C42 1.369(12) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?

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
O9 Mn1 O1 96.3(2) 6_575 . ?
O9 Mn1 O7 109.1(2) 6_575 . ?
O1 Mn1 O7 90.2(2) . . ?
O9 Mn1 N2 155.6(2) 6_575 . ?
O1 Mn1 N2 80.9(2) . . ?
O7 Mn1 N2 95.1(2) . . ?
O9 Mn1 N1 89.5(2) 6_575 . ?
O1 Mn1 N1 124.0(2) . . ?
O7 Mn1 N1 139.6(2) . . ?
N2 Mn1 N1 72.7(2) . . ?
O9 Mn1 O6 97.1(2) 6_575 . ?
O1 Mn1 O6 147.21(19) . . ?
O7 Mn1 O6 57.11(18) . . ?
N2 Mn1 O6 98.0(2) . . ?
N1 Mn1 O6 85.91(19) . . ?
O8 Mn2 O2 98.0(2) . 6_576 ?
O8 Mn2 O3 91.5(2) . . ?
O2 Mn2 O3 102.7(2) 6_576 . ?
O8 Mn2 N4 82.9(2) . . ?
O2 Mn2 N4 162.1(2) 6_576 . ?
O3 Mn2 N4 95.1(2) . . ?
O8 Mn2 N3 128.0(2) . . ?
O2 Mn2 N3 93.2(2) 6_576 . ?
O3 Mn2 N3 134.9(2) . . ?
N4 Mn2 N3 72.7(3) . . ?
O8 Mn2 O4 147.41(19) . . ?
O2 Mn2 O4 97.8(2) 6_576 . ?
O3 Mn2 O4 57.17(19) . . ?
N4 Mn2 O4 90.5(2) . . ?
N3 Mn2 O4 79.2(2) . . ?
C19 N1 C23 117.9(7) . . ?
C19 N1 Mn1 126.1(5) . . ?
C23 N1 Mn1 116.1(5) . . ?
C30 N2 C27 118.9(9) . . ?
C30 N2 Mn1 125.4(7) . . ?
C27 N2 Mn1 115.1(6) . . ?
C31 N3 C35 116.4(9) . . ?
C31 N3 Mn2 126.1(7) . . ?
C35 N3 Mn2 115.4(6) . . ?
C42 N4 C39 117.9(8) . . ?
C42 N4 Mn2 125.2(7) . . ?
C39 N4 Mn2 116.4(6) . . ?
C1 O1 Mn1 156.5(6) . . ?
C1 O2 Mn2 116.0(5) . 6_575 ?
C5 O3 Mn2 91.7(5) . . ?
C5 O4 Mn2 88.8(5) . . ?
C7 O5 C9 117.2(6) . . ?
C10 O6 Mn1 89.5(4) . . ?
C10 O7 Mn1 92.5(4) . . ?
C14 O8 Mn2 158.6(5) . . ?
C14 O9 Mn1 116.4(5) . 6_576 ?
C16 O10 C18 118.3(7) . . ?
O1 C1 O2 124.0(7) . . ?
O1 C1 C2 118.1(6) . . ?
O2 C1 C2 117.6(6) . . ?
C8 C2 C3 120.1(6) . . ?
C8 C2 C1 119.8(6) . . ?
C3 C2 C1 120.1(6) . . ?
C2 C3 C4 119.2(6) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C6 C4 C3 120.7(6) . . ?
C6 C4 C5 118.3(6) . . ?
C3 C4 C5 121.0(6) . . ?
O4 C5 O3 121.8(7) . . ?
O4 C5 C4 119.4(7) . . ?
O3 C5 C4 118.7(7) . . ?
C7 C6 C4 119.3(6) . . ?
C7 C6 H6 120.3 . . ?
C4 C6 H6 120.3 . . ?
C8 C7 C6 120.3(7) . . ?
C8 C7 O5 116.0(6) . . ?
C6 C7 O5 123.7(7) . . ?
C7 C8 C2 120.4(6) . . ?
C7 C8 H8 119.8 . . ?
C2 C8 H8 119.8 . . ?
O5 C9 H9C 109.5 . . ?
O5 C9 H9B 109.5 . . ?
H9C C9 H9B 109.5 . . ?
O5 C9 H9A 109.5 . . ?
H9C C9 H9A 109.5 . . ?
H9B C9 H9A 109.5 . . ?
O6 C10 O7 120.9(6) . . ?
O6 C10 C11 119.8(7) . . ?
O7 C10 C11 119.2(6) . . ?
C17 C11 C12 121.7(6) . . ?
C17 C11 C10 118.4(6) . . ?
C12 C11 C10 119.9(6) . . ?
C11 C12 C13 117.8(6) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C15 C13 C12 121.5(6) . . ?
C15 C13 C14 119.3(6) . . ?
C12 C13 C14 119.2(6) . . ?
O9 C14 O8 122.8(7) . . ?
O9 C14 C13 118.9(7) . . ?
O8 C14 C13 118.2(6) . . ?
C13 C15 C16 120.2(6) . . ?
C13 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
O10 C16 C15 126.0(6) . . ?
O10 C16 C17 114.3(7) . . ?
C15 C16 C17 119.7(7) . . ?
C11 C17 C16 119.0(7) . . ?
C11 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
O10 C18 H18A 109.5 . . ?
O10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 121.4(9) . . ?
N1 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C21 C20 C19 122.2(10) . . ?
C21 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
C20 C21 C22 117.6(9) . . ?
C20 C21 H21 121.2 . . ?
C22 C21 H21 121.2 . . ?
C21 C22 C23 118.7(9) . . ?
C21 C22 C24 123.1(10) . . ?
C23 C22 C24 118.2(10) . . ?
N1 C23 C22 122.1(8) . . ?
N1 C23 C27 116.6(7) . . ?
C22 C23 C27 121.3(8) . . ?
C25 C24 C22 122.0(11) . . ?
C25 C24 H24 119.0 . . ?
C22 C24 H24 119.0 . . ?
C24 C25 C26 120.0(11) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C28 C26 C27 115.7(10) . . ?
C28 C26 C25 123.0(11) . . ?
C27 C26 C25 121.3(10) . . ?
N2 C27 C26 123.9(9) . . ?
N2 C27 C23 118.9(8) . . ?
C26 C27 C23 117.1(8) . . ?
C29 C28 C26 122.0(11) . . ?
C29 C28 H28 119.0 . . ?
C26 C28 H28 119.0 . . ?
C28 C29 C30 119.5(11) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
N2 C30 C29 119.9(10) . . ?
N2 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
N3 C31 C32 124.0(10) . . ?
N3 C31 H31 118.0 . . ?
C32 C31 H31 118.0 . . ?
C33 C32 C31 119.0(10) . . ?
C33 C32 H32 120.5 . . ?
C31 C32 H32 120.5 . . ?
C32 C33 C34 119.7(11) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C35 C34 C33 117.3(10) . . ?
C35 C34 C36 118.0(11) . . ?
C33 C34 C36 124.7(11) . . ?
N3 C35 C34 123.4(9) . . ?
N3 C35 C39 116.0(8) . . ?
C34 C35 C39 120.6(9) . . ?
C37 C36 C34 121.7(12) . . ?
C37 C36 H36 119.2 . . ?
C34 C36 H36 119.2 . . ?
C36 C37 C38 122.9(12) . . ?
C36 C37 H37 118.6 . . ?
C38 C37 H37 118.6 . . ?
C40 C38 C39 115.8(10) . . ?
C40 C38 C37 126.6(11) . . ?
C39 C38 C37 117.5(11) . . ?
N4 C39 C38 122.4(9) . . ?
N4 C39 C35 118.3(8) . . ?
C38 C39 C35 119.3(9) . . ?
C41 C40 C38 120.3(11) . . ?
C41 C40 H40 119.8 . . ?
C38 C40 H40 119.8 . . ?
C40 C41 C42 119.9(12) . . ?
C40 C41 H41 120.1 . . ?
C42 C41 H41 120.1 . . ?
N4 C42 C41 123.5(11) . . ?
N4 C42 H42 118.2 . . ?
C41 C42 H42 118.2 . . ?

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
Mn1 O1 C1 O2 -83.9(15) . . . . ?
Mn1 O1 C1 C2 103.3(13) . . . . ?
Mn2 O2 C1 O1 3.7(11) 6_575 . . . ?
Mn2 O2 C1 C2 176.6(5) 6_575 . . . ?
O1 C1 C2 C8 168.7(7) . . . . ?
O2 C1 C2 C8 -4.6(11) . . . . ?
O1 C1 C2 C3 -12.8(11) . . . . ?
O2 C1 C2 C3 173.9(7) . . . . ?
C8 C2 C3 C4 -1.6(11) . . . . ?
C1 C2 C3 C4 179.8(6) . . . . ?
C2 C3 C4 C6 0.9(11) . . . . ?
C2 C3 C4 C5 -179.6(6) . . . . ?
Mn2 O4 C5 O3 -7.1(8) . . . . ?
Mn2 O4 C5 C4 173.0(6) . . . . ?
Mn2 O3 C5 O4 7.3(9) . . . . ?
Mn2 O3 C5 C4 -172.8(6) . . . . ?
C6 C4 C5 O4 1.9(11) . . . . ?
C3 C4 C5 O4 -177.6(7) . . . . ?
C6 C4 C5 O3 -178.0(7) . . . . ?
C3 C4 C5 O3 2.5(11) . . . . ?
C3 C4 C6 C7 0.8(11) . . . . ?
C5 C4 C6 C7 -178.7(7) . . . . ?
C4 C6 C7 C8 -1.9(12) . . . . ?
C4 C6 C7 O5 178.2(7) . . . . ?
C9 O5 C7 C8 171.3(7) . . . . ?
C9 O5 C7 C6 -8.8(13) . . . . ?
C6 C7 C8 C2 1.2(13) . . . . ?
O5 C7 C8 C2 -178.9(7) . . . . ?
C3 C2 C8 C7 0.6(12) . . . . ?
C1 C2 C8 C7 179.2(7) . . . . ?
Mn1 O6 C10 O7 0.9(8) . . . . ?
Mn1 O6 C10 C11 -178.7(6) . . . . ?
Mn1 O7 C10 O6 -0.9(8) . . . . ?
Mn1 O7 C10 C11 178.7(6) . . . . ?
O6 C10 C11 C17 4.3(11) . . . . ?
O7 C10 C11 C17 -175.3(7) . . . . ?
O6 C10 C11 C12 -174.3(7) . . . . ?
O7 C10 C11 C12 6.2(11) . . . . ?
C17 C11 C12 C13 2.0(10) . . . . ?
C10 C11 C12 C13 -179.6(6) . . . . ?
C11 C12 C13 C15 -1.5(10) . . . . ?
C11 C12 C13 C14 179.5(6) . . . . ?
Mn1 O9 C14 O8 6.8(10) 6_576 . . . ?
Mn1 O9 C14 C13 -171.3(4) 6_576 . . . ?
Mn2 O8 C14 O9 78.1(15) . . . . ?
Mn2 O8 C14 C13 -103.8(13) . . . . ?
C15 C13 C14 O9 14.6(10) . . . . ?
C12 C13 C14 O9 -166.4(6) . . . . ?
C15 C13 C14 O8 -163.6(7) . . . . ?
C12 C13 C14 O8 15.4(10) . . . . ?
C12 C13 C15 C16 1.3(11) . . . . ?
C14 C13 C15 C16 -179.6(6) . . . . ?
C18 O10 C16 C15 0.4(12) . . . . ?
C18 O10 C16 C17 -178.4(7) . . . . ?
C13 C15 C16 O10 179.8(7) . . . . ?
C13 C15 C16 C17 -1.5(10) . . . . ?
C12 C11 C17 C16 -2.2(10) . . . . ?
C10 C11 C17 C16 179.3(6) . . . . ?
O10 C16 C17 C11 -179.2(6) . . . . ?
C15 C16 C17 C11 1.9(10) . . . . ?
C23 N1 C19 C20 -0.1(11) . . . . ?
Mn1 N1 C19 C20 179.2(6) . . . . ?
N1 C19 C20 C21 -2.9(15) . . . . ?
C19 C20 C21 C22 2.0(16) . . . . ?
C20 C21 C22 C23 1.4(15) . . . . ?
C20 C21 C22 C24 -178.9(9) . . . . ?
C19 N1 C23 C22 3.6(11) . . . . ?
Mn1 N1 C23 C22 -175.7(6) . . . . ?
C19 N1 C23 C27 -177.4(7) . . . . ?
Mn1 N1 C23 C27 3.3(8) . . . . ?
C21 C22 C23 N1 -4.4(13) . . . . ?
C24 C22 C23 N1 175.9(8) . . . . ?
C21 C22 C23 C27 176.7(8) . . . . ?
C24 C22 C23 C27 -3.0(12) . . . . ?
C21 C22 C24 C25 -177.1(11) . . . . ?
C23 C22 C24 C25 2.6(16) . . . . ?
C22 C24 C25 C26 -0.3(17) . . . . ?
C24 C25 C26 C28 178.1(11) . . . . ?
C24 C25 C26 C27 -1.6(15) . . . . ?
C30 N2 C27 C26 1.5(12) . . . . ?
Mn1 N2 C27 C26 173.2(6) . . . . ?
C30 N2 C27 C23 -179.5(7) . . . . ?
Mn1 N2 C27 C23 -7.9(9) . . . . ?
C28 C26 C27 N2 0.4(13) . . . . ?
C25 C26 C27 N2 -179.8(8) . . . . ?
C28 C26 C27 C23 -178.5(8) . . . . ?
C25 C26 C27 C23 1.2(12) . . . . ?
N1 C23 C27 N2 3.1(10) . . . . ?
C22 C23 C27 N2 -177.9(7) . . . . ?
N1 C23 C27 C26 -177.8(7) . . . . ?
C22 C23 C27 C26 1.1(11) . . . . ?
C27 C26 C28 C29 -0.8(16) . . . . ?
C25 C26 C28 C29 179.4(10) . . . . ?
C26 C28 C29 C30 -0.6(19) . . . . ?
C27 N2 C30 C29 -3.0(13) . . . . ?
Mn1 N2 C30 C29 -173.7(7) . . . . ?
C28 C29 C30 N2 2.7(17) . . . . ?
C35 N3 C31 C32 3.9(13) . . . . ?
Mn2 N3 C31 C32 166.7(7) . . . . ?
N3 C31 C32 C33 -0.4(15) . . . . ?
C31 C32 C33 C34 -1.5(15) . . . . ?
C32 C33 C34 C35 -0.3(14) . . . . ?
C32 C33 C34 C36 -177.9(9) . . . . ?
C31 N3 C35 C34 -5.8(12) . . . . ?
Mn2 N3 C35 C34 -170.4(6) . . . . ?
C31 N3 C35 C39 174.7(7) . . . . ?
Mn2 N3 C35 C39 10.1(9) . . . . ?
C33 C34 C35 N3 4.1(13) . . . . ?
C36 C34 C35 N3 -178.1(8) . . . . ?
C33 C34 C35 C39 -176.5(8) . . . . ?
C36 C34 C35 C39 1.3(12) . . . . ?
C35 C34 C36 C37 0.3(15) . . . . ?
C33 C34 C36 C37 177.9(11) . . . . ?
C34 C36 C37 C38 -3.1(18) . . . . ?
C36 C37 C38 C40 -178.5(11) . . . . ?
C36 C37 C38 C39 4.1(16) . . . . ?
C42 N4 C39 C38 -1.1(12) . . . . ?
Mn2 N4 C39 C38 171.6(6) . . . . ?
C42 N4 C39 C35 -179.2(7) . . . . ?
Mn2 N4 C39 C35 -6.5(9) . . . . ?
C40 C38 C39 N4 1.8(13) . . . . ?
C37 C38 C39 N4 179.5(8) . . . . ?
C40 C38 C39 C35 179.9(8) . . . . ?
C37 C38 C39 C35 -2.4(13) . . . . ?
N3 C35 C39 N4 -2.6(11) . . . . ?
C34 C35 C39 N4 178.0(7) . . . . ?
N3 C35 C39 C38 179.3(7) . . . . ?
C34 C35 C39 C38 -0.2(12) . . . . ?
C39 C38 C40 C41 -2.6(16) . . . . ?
C37 C38 C40 C41 180.0(11) . . . . ?
C38 C40 C41 C42 2.6(19) . . . . ?
C39 N4 C42 C41 1.1(14) . . . . ?
Mn2 N4 C42 C41 -170.9(8) . . . . ?
C40 C41 C42 N4 -1.9(18) . . . . ?

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
C42 H42 O10 0.93 2.66 3.350(12) 131.8 5_776
C19 H19 O6 0.93 2.50 3.170(10) 128.9 2_755

_refine_diff_density_max         0.748
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_510-15Cd
_database_code_depnum_ccdc_archive 'CCDC 2269630'
_audit_update_record             
;
2023-06-13 deposited with the CCDC.	2023-08-01 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            'C14 H17 Cd N O8'
_chemical_formula_weight         439.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd 0.1185 4.6533 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   9.3015(5)
_cell_length_b                   10.1706(6)
_cell_length_c                   10.2299(5)
_cell_angle_alpha                68.453(5)
_cell_angle_beta                 81.292(4)
_cell_angle_gamma                67.661(5)
_cell_volume                     832.50(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5039
_cell_measurement_theta_min      4.997
_cell_measurement_theta_max      65.977

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   0.141
_exptl_transmission_factor_max   0.152
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    10.901
_shelx_estimated_absorpt_T_min   0.208
_shelx_estimated_absorpt_T_max   0.244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.208
_exptl_absorpt_correction_T_max  0.244
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5039
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.997
_diffrn_reflns_theta_max         65.977
_diffrn_reflns_theta_full        65.977
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2869
_reflns_number_gt                2740
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0654P)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_number_reflns         2869
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
Cd1 Cd 0.54436(3) 0.75979(3) -0.08757(2) 0.03062(13) Uani 1 1 d . . . . .
N1 N 0.7572(4) 0.8329(4) -0.1366(4) 0.0368(7) Uani 1 1 d . . . . .
O1 O 0.3773(4) 0.6866(4) 0.1068(3) 0.0450(7) Uani 1 1 d . . . . .
O2 O 0.5524(4) 0.7613(4) 0.1465(3) 0.0439(7) Uani 1 1 d . . . . .
O3 O 0.5842(4) 0.7553(5) 0.6457(3) 0.0526(9) Uani 1 1 d . . . . .
O4 O 0.4046(3) 0.6994(3) 0.7962(3) 0.0390(6) Uani 1 1 d . . . . .
O5 O 0.0542(4) 0.6068(5) 0.5395(3) 0.0605(10) Uani 1 1 d . . . . .
O6 O 0.3822(4) 1.0065(4) -0.1701(4) 0.0502(8) Uani 1 1 d . . . . .
H1W H 0.3337 1.0415 -0.2459 0.060 Uiso 1 1 d R U . . .
H2W H 0.4093 1.0741 -0.1641 0.060 Uiso 1 1 d R U . . .
O7 O 0.7048(4) 0.5024(3) -0.0165(3) 0.0418(7) Uani 1 1 d . . . . .
H3W H 0.6943 0.4592 -0.0699 0.050 Uiso 1 1 d R U . . .
H4W H 0.6790 0.4546 0.0655 0.050 Uiso 1 1 d R U . . .
O8 O 0.2346(5) 0.1432(6) 0.5796(4) 0.0817(14) Uani 1 1 d . . . . .
H5W H 0.2832 0.1853 0.5134 0.098 Uiso 1 1 d R U . . .
H6W H 0.1512 0.2149 0.5449 0.098 Uiso 1 1 d R U . . .
C1 C 0.4404(5) 0.7145(4) 0.1886(4) 0.0345(8) Uani 1 1 d . . . . .
C2 C 0.3812(4) 0.6924(4) 0.3366(4) 0.0308(8) Uani 1 1 d . . . . .
C3 C 0.4554(4) 0.7104(4) 0.4338(4) 0.0283(7) Uani 1 1 d . . . . .
H3 H 0.5459 0.7330 0.4083 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3943(4) 0.6945(4) 0.5690(4) 0.0287(7) Uani 1 1 d . . . . .
C5 C 0.4680(5) 0.7168(4) 0.6761(4) 0.0337(8) Uani 1 1 d . . . . .
C6 C 0.2607(5) 0.6573(4) 0.6078(4) 0.0329(8) Uani 1 1 d . . . . .
H6 H 0.2199 0.6456 0.6984 0.040 Uiso 1 1 calc R U . . .
C7 C 0.1894(5) 0.6380(5) 0.5107(4) 0.0364(9) Uani 1 1 d . . . . .
C8 C 0.0122(7) 0.5459(8) 0.6825(6) 0.0710(16) Uani 1 1 d . . . . .
H8A H 0.0911 0.4503 0.7264 0.107 Uiso 1 1 calc R U . . .
H8B H -0.0851 0.5319 0.6871 0.107 Uiso 1 1 calc R U . . .
H8C H 0.0022 0.6142 0.7306 0.107 Uiso 1 1 calc R U . . .
C9 C 0.2480(5) 0.6569(5) 0.3758(4) 0.0352(8) Uani 1 1 d . . . . .
H9 H 0.1978 0.6456 0.3108 0.042 Uiso 1 1 calc R U . . .
C10 C 0.8571(6) 0.7953(6) -0.0366(6) 0.0578(12) Uani 1 1 d . . . . .
H10 H 0.8383 0.7389 0.0547 0.069 Uiso 1 1 calc R U . . .
C11 C 0.9867(6) 0.8365(7) -0.0625(8) 0.0781(19) Uani 1 1 d . . . . .
H11 H 1.0534 0.8086 0.0099 0.094 Uiso 1 1 calc R U . . .
C12 C 1.0154(7) 0.9186(7) -0.1958(10) 0.084(2) Uani 1 1 d . . . . .
H12 H 1.1024 0.9470 -0.2165 0.101 Uiso 1 1 calc R U . . .
C13 C 0.9130(8) 0.9585(6) -0.2985(8) 0.077(2) Uani 1 1 d . . . . .
H13 H 0.9297 1.0149 -0.3904 0.092 Uiso 1 1 calc R U . . .
C14 C 0.7860(6) 0.9149(5) -0.2652(5) 0.0511(11) Uani 1 1 d . . . . .
H14 H 0.7168 0.9442 -0.3360 0.061 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
Cd1 O4 2.256(3) 1_554 ?
Cd1 O6 2.288(3) . ?
Cd1 N1 2.295(3) . ?
Cd1 O7 2.360(3) . ?
Cd1 O1 2.404(3) . ?
Cd1 O2 2.413(3) . ?
N1 C14 1.325(6) . ?
N1 C10 1.337(6) . ?
O1 C1 1.254(5) . ?
O2 C1 1.261(5) . ?
O3 C5 1.245(5) . ?
O4 C5 1.261(5) . ?
O4 Cd1 2.257(3) 1_556 ?
O5 C7 1.375(5) . ?
O5 C8 1.422(6) . ?
O6 H1W 0.8435 . ?
O6 H2W 0.8408 . ?
O7 H3W 0.8526 . ?
O7 H4W 0.8517 . ?
O8 H5W 0.8297 . ?
O8 H6W 0.8500 . ?
C1 C2 1.496(5) . ?
C2 C9 1.382(6) . ?
C2 C3 1.392(5) . ?
C3 C4 1.389(5) . ?
C3 H3 0.9300 . ?
C4 C6 1.393(5) . ?
C4 C5 1.499(5) . ?
C6 C7 1.381(5) . ?
C6 H6 0.9300 . ?
C7 C9 1.377(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9 0.9300 . ?
C10 C11 1.380(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.360(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.368(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(8) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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
O4 Cd1 O6 89.24(11) 1_554 . ?
O4 Cd1 N1 136.12(11) 1_554 . ?
O6 Cd1 N1 90.73(12) . . ?
O4 Cd1 O7 86.60(11) 1_554 . ?
O6 Cd1 O7 175.59(10) . . ?
N1 Cd1 O7 91.25(11) . . ?
O4 Cd1 O1 83.57(10) 1_554 . ?
O6 Cd1 O1 94.70(12) . . ?
N1 Cd1 O1 140.07(11) . . ?
O7 Cd1 O1 86.30(11) . . ?
O4 Cd1 O2 137.44(10) 1_554 . ?
O6 Cd1 O2 94.03(12) . . ?
N1 Cd1 O2 86.32(12) . . ?
O7 Cd1 O2 90.03(11) . . ?
O1 Cd1 O2 53.87(10) . . ?
C14 N1 C10 117.1(4) . . ?
C14 N1 Cd1 121.4(3) . . ?
C10 N1 Cd1 121.5(3) . . ?
C1 O1 Cd1 93.2(2) . . ?
C1 O2 Cd1 92.6(2) . . ?
C5 O4 Cd1 104.2(2) . 1_556 ?
C7 O5 C8 118.4(4) . . ?
Cd1 O6 H1W 121.4 . . ?
Cd1 O6 H2W 119.1 . . ?
H1W O6 H2W 108.2 . . ?
Cd1 O7 H3W 111.3 . . ?
Cd1 O7 H4W 110.8 . . ?
H3W O7 H4W 105.4 . . ?
H5W O8 H6W 88.4 . . ?
O1 C1 O2 120.4(4) . . ?
O1 C1 C2 119.5(4) . . ?
O2 C1 C2 120.1(4) . . ?
C9 C2 C3 119.7(3) . . ?
C9 C2 C1 118.9(4) . . ?
C3 C2 C1 121.3(3) . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C6 C4 C3 119.9(3) . . ?
C6 C4 C5 118.4(3) . . ?
C3 C4 C5 121.8(3) . . ?
O3 C5 O4 121.6(4) . . ?
O3 C5 C4 121.1(3) . . ?
O4 C5 C4 117.3(3) . . ?
C7 C6 C4 119.6(3) . . ?
C7 C6 H6 120.2 . . ?
C4 C6 H6 120.2 . . ?
O5 C7 C6 122.9(3) . . ?
O5 C7 C9 116.4(4) . . ?
C6 C7 C9 120.6(4) . . ?
O5 C8 H8A 109.5 . . ?
O5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C9 C7 120.3(4) . . ?
C2 C9 H9 119.8 . . ?
C7 C9 H9 119.8 . . ?
N1 C10 C11 123.0(5) . . ?
N1 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
C12 C11 C10 118.9(6) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 118.4(5) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 119.7(6) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
N1 C14 C13 122.9(6) . . ?
N1 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cd1 O1 C1 O2 -0.9(4) . . . . ?
Cd1 O1 C1 C2 178.8(3) . . . . ?
Cd1 O2 C1 O1 0.9(4) . . . . ?
Cd1 O2 C1 C2 -178.8(3) . . . . ?
O1 C1 C2 C9 -6.7(6) . . . . ?
O2 C1 C2 C9 173.0(4) . . . . ?
O1 C1 C2 C3 174.8(4) . . . . ?
O2 C1 C2 C3 -5.5(6) . . . . ?
C9 C2 C3 C4 -0.9(6) . . . . ?
C1 C2 C3 C4 177.6(3) . . . . ?
C2 C3 C4 C6 1.4(5) . . . . ?
C2 C3 C4 C5 -178.4(3) . . . . ?
Cd1 O4 C5 O3 1.7(5) 1_556 . . . ?
Cd1 O4 C5 C4 -176.1(3) 1_556 . . . ?
C6 C4 C5 O3 -177.4(4) . . . . ?
C3 C4 C5 O3 2.4(6) . . . . ?
C6 C4 C5 O4 0.4(5) . . . . ?
C3 C4 C5 O4 -179.7(3) . . . . ?
C3 C4 C6 C7 -0.6(6) . . . . ?
C5 C4 C6 C7 179.2(4) . . . . ?
C8 O5 C7 C6 -20.3(7) . . . . ?
C8 O5 C7 C9 162.8(5) . . . . ?
C4 C6 C7 O5 -177.5(4) . . . . ?
C4 C6 C7 C9 -0.7(6) . . . . ?
C3 C2 C9 C7 -0.5(6) . . . . ?
C1 C2 C9 C7 -179.1(4) . . . . ?
O5 C7 C9 C2 178.3(4) . . . . ?
C6 C7 C9 C2 1.3(6) . . . . ?
C14 N1 C10 C11 -0.8(8) . . . . ?
Cd1 N1 C10 C11 179.6(4) . . . . ?
N1 C10 C11 C12 -0.2(9) . . . . ?
C10 C11 C12 C13 0.7(10) . . . . ?
C11 C12 C13 C14 -0.2(9) . . . . ?
C10 N1 C14 C13 1.4(7) . . . . ?
Cd1 N1 C14 C13 -179.0(4) . . . . ?
C12 C13 C14 N1 -0.9(9) . . . . ?

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
C10 H10 O2 0.93 2.64 3.212(6) 120.8 .
O8 H6W O5 0.85 2.10 2.948(6) 179.3 2_566
O8 H5W O3 0.83 1.94 2.760(5) 168.7 2_666
O7 H4W O4 0.85 2.01 2.797(4) 154.1 2_666
O7 H3W O1 0.85 2.01 2.788(4) 152.0 2_665
O6 H2W O2 0.84 1.91 2.750(4) 173.8 2_675
O6 H1W O8 0.84 1.88 2.715(5) 171.8 1_564
C10 H10 O2 0.93 2.64 3.212(6) 120.8 .
O8 H5W O3 0.83 1.94 2.760(5) 168.7 2_666
O7 H4W O4 0.85 2.01 2.797(4) 154.1 2_666
O7 H3W O1 0.85 2.01 2.788(4) 152.0 2_665
O6 H2W O2 0.84 1.91 2.750(4) 173.8 2_675
O6 H1W O8 0.84 1.88 2.715(5) 171.8 1_564
C10 H10 O2 0.93 2.64 3.212(6) 120.8 .
O8 H5W O3 0.83 1.94 2.760(5) 168.7 2_666
O7 H4W O4 0.85 2.01 2.797(4) 154.1 2_666
O7 H3W O1 0.85 2.01 2.788(4) 152.0 2_665
O6 H2W O2 0.84 1.91 2.750(4) 173.8 2_675
O6 H1W O8 0.84 1.88 2.715(5) 171.8 1_564
O6 H1W O8 0.84 1.88 2.715(5) 171.8 1_564
O6 H2W O2 0.84 1.91 2.750(4) 173.8 2_675
O7 H3W O1 0.85 2.01 2.788(4) 152.0 2_665
O7 H4W O4 0.85 2.01 2.797(4) 154.1 2_666
O8 H5W O3 0.83 1.94 2.760(5) 168.7 2_666
C10 H10 O2 0.93 2.64 3.212(6) 120.8 .
O6 H1W O8 0.84 1.88 2.715(5) 171.8 1_564
O6 H2W O2 0.84 1.91 2.750(4) 173.8 2_675
O7 H3W O1 0.85 2.01 2.788(4) 152.0 2_665
O7 H4W O4 0.85 2.01 2.797(4) 154.1 2_666
O8 H5W O3 0.83 1.94 2.760(5) 168.7 2_666
C10 H10 O2 0.93 2.64 3.212(6) 120.8 .

_refine_diff_density_max         1.137
_refine_diff_density_min         -0.925
_refine_diff_density_rms         0.114

####################################################################### 
# 
# 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_510-11Co
_database_code_depnum_ccdc_archive 'CCDC 2269629'
_audit_update_record             
;
2023-06-13 deposited with the CCDC.	2023-08-01 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            'C19 H16 Co N2 O5'
_chemical_formula_weight         411.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   16.0459(6)
_cell_length_b                   12.0320(4)
_cell_length_c                   19.4535(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.900(4)
_cell_angle_gamma                90
_cell_volume                     3612.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6302
_cell_measurement_theta_min      4.660
_cell_measurement_theta_max      65.987

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_F_000             1688
_exptl_transmission_factor_min   0.287
_exptl_transmission_factor_max   0.289
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    7.748
_shelx_estimated_absorpt_T_min   0.321
_shelx_estimated_absorpt_T_max   0.370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.321
_exptl_absorpt_correction_T_max  0.370
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6302
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.660
_diffrn_reflns_theta_max         65.987
_diffrn_reflns_theta_full        65.987
_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             3136
_reflns_number_gt                2533
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0588P)²+2.3655P] 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         3136
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
Co1 Co 1.11786(3) 0.75427(4) 0.47533(3) 0.02933(16) Uani 1 1 d . . . . .
N1 N 1.11902(16) 0.8172(2) 0.58014(14) 0.0389(6) Uani 1 1 d . . . . .
N2 N 1.12213(16) 0.6963(2) 0.37138(14) 0.0379(6) Uani 1 1 d . . . . .
O1 O 1.01615(12) 0.64019(17) 0.47477(12) 0.0419(6) Uani 1 1 d . . . . .
O2 O 0.97884(12) 0.80714(17) 0.43427(12) 0.0395(5) Uani 1 1 d . . . . .
O3 O 0.79099(13) 0.35817(17) 0.47708(13) 0.0457(6) Uani 1 1 d . . . . .
O4 O 0.65455(12) 0.40942(16) 0.45209(12) 0.0404(6) Uani 1 1 d . . . . .
O5 O 0.65644(12) 0.81444(17) 0.37850(13) 0.0414(6) Uani 1 1 d . . . . .
C1 C 0.95911(18) 0.7116(2) 0.44951(16) 0.0292(6) Uani 1 1 d . . . . .
C2 C 0.86514(17) 0.6807(2) 0.43813(14) 0.0256(6) Uani 1 1 d . . . . .
C3 C 0.84363(16) 0.5724(2) 0.45231(14) 0.0254(6) Uani 1 1 d . . . . .
H3 H 0.8868 0.5193 0.4682 0.031 Uiso 1 1 calc R U . . .
C4 C 0.75723(16) 0.5446(2) 0.44244(14) 0.0233(6) Uani 1 1 d . . . . .
C5 C 0.73303(17) 0.4289(2) 0.45863(14) 0.0259(6) Uani 1 1 d . . . . .
C6 C 0.69237(16) 0.6238(2) 0.41797(14) 0.0251(6) Uani 1 1 d . . . . .
H6 H 0.6345 0.6049 0.4114 0.030 Uiso 1 1 calc R U . . .
C7 C 0.71455(18) 0.7305(2) 0.40361(15) 0.0258(6) Uani 1 1 d . . . . .
C8 C 0.5670(2) 0.7914(3) 0.3686(2) 0.0549(10) Uani 1 1 d . . . . .
H8A H 0.5471 0.7408 0.3294 0.082 Uiso 1 1 calc R U . . .
H8B H 0.5345 0.8593 0.3585 0.082 Uiso 1 1 calc R U . . .
H8C H 0.5589 0.7586 0.4113 0.082 Uiso 1 1 calc R U . . .
C9 C 0.80146(18) 0.7590(2) 0.41363(15) 0.0274(6) Uani 1 1 d . . . . .
H9 H 0.8162 0.8308 0.4037 0.033 Uiso 1 1 calc R U . . .
C10 C 1.1499(2) 0.7593(3) 0.6402(2) 0.0502(9) Uani 1 1 d . . . . .
H10 H 1.1717 0.6885 0.6370 0.060 Uiso 1 1 calc R U . . .
C11 C 1.1510(3) 0.7991(4) 0.7066(2) 0.0658(11) Uani 1 1 d . . . . .
H11 H 1.1736 0.7564 0.7472 0.079 Uiso 1 1 calc R U . . .
C12 C 1.1178(3) 0.9039(4) 0.7118(2) 0.0711(12) Uani 1 1 d . . . . .
H12 H 1.1179 0.9332 0.7561 0.085 Uiso 1 1 calc R U . . .
C13 C 1.0848(3) 0.9635(3) 0.6502(2) 0.0677(12) Uani 1 1 d . . . . .
H13 H 1.0610 1.0336 0.6518 0.081 Uiso 1 1 calc R U . . .
C14 C 1.0876(2) 0.9181(3) 0.58627(19) 0.0501(9) Uani 1 1 d . . . . .
H14 H 1.0664 0.9599 0.5450 0.060 Uiso 1 1 calc R U . . .
C15 C 1.1343(3) 0.5895(3) 0.3598(2) 0.0539(10) Uani 1 1 d . . . . .
H15 H 1.1423 0.5403 0.3980 0.065 Uiso 1 1 calc R U . . .
C16 C 1.1357(3) 0.5479(3) 0.2945(2) 0.0734(13) Uani 1 1 d . . . . .
H16 H 1.1455 0.4727 0.2891 0.088 Uiso 1 1 calc R U . . .
C17 C 1.1227(3) 0.6187(4) 0.2373(2) 0.0749(13) Uani 1 1 d . . . . .
H17 H 1.1223 0.5927 0.1922 0.090 Uiso 1 1 calc R U . . .
C18 C 1.1103(3) 0.7286(3) 0.2488(2) 0.0643(12) Uani 1 1 d . . . . .
H18 H 1.1017 0.7788 0.2112 0.077 Uiso 1 1 calc R U . . .
C19 C 1.1106(2) 0.7648(3) 0.3150(2) 0.0506(9) Uani 1 1 d . . . . .
H19 H 1.1024 0.8402 0.3215 0.061 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 O3 2.021(2) 5_766 ?
Co1 O4 2.0450(19) 3 ?
Co1 O1 2.1303(19) . ?
Co1 N2 2.158(3) . ?
Co1 N1 2.170(3) . ?
Co1 O2 2.246(2) . ?
N1 C14 1.332(4) . ?
N1 C10 1.333(4) . ?
N2 C15 1.329(4) . ?
N2 C19 1.344(4) . ?
O1 C1 1.253(3) . ?
O2 C1 1.249(3) . ?
O3 C5 1.239(3) . ?
O3 Co1 2.021(2) 5_766 ?
O4 C5 1.253(3) . ?
O4 Co1 2.0450(19) 3_445 ?
O5 C7 1.370(3) . ?
O5 C8 1.423(4) . ?
C1 C2 1.509(4) . ?
C2 C9 1.375(4) . ?
C2 C3 1.395(4) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C6 1.395(4) . ?
C4 C5 1.501(4) . ?
C6 C7 1.381(4) . ?
C6 H6 0.9300 . ?
C7 C9 1.397(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9 0.9300 . ?
C10 C11 1.372(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.371(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.358(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

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
O3 Co1 O4 119.76(8) 5_766 3 ?
O3 Co1 O1 91.62(8) 5_766 . ?
O4 Co1 O1 148.61(8) 3 . ?
O3 Co1 N2 90.47(10) 5_766 . ?
O4 Co1 N2 90.17(9) 3 . ?
O1 Co1 N2 90.46(9) . . ?
O3 Co1 N1 89.10(10) 5_766 . ?
O4 Co1 N1 87.73(9) 3 . ?
O1 Co1 N1 92.23(9) . . ?
N2 Co1 N1 177.29(9) . . ?
O3 Co1 O2 151.20(8) 5_766 . ?
O4 Co1 O2 88.90(7) 3 . ?
O1 Co1 O2 59.72(7) . . ?
N2 Co1 O2 92.39(9) . . ?
N1 Co1 O2 89.27(9) . . ?
C14 N1 C10 117.1(3) . . ?
C14 N1 Co1 119.7(2) . . ?
C10 N1 Co1 123.1(2) . . ?
C15 N2 C19 116.7(3) . . ?
C15 N2 Co1 121.0(2) . . ?
C19 N2 Co1 122.3(2) . . ?
C1 O1 Co1 92.08(16) . . ?
C1 O2 Co1 86.94(17) . . ?
C5 O3 Co1 169.8(2) . 5_766 ?
C5 O4 Co1 119.41(18) . 3_445 ?
C7 O5 C8 117.9(2) . . ?
O2 C1 O1 121.2(2) . . ?
O2 C1 C2 120.0(3) . . ?
O1 C1 C2 118.8(2) . . ?
C9 C2 C3 120.5(2) . . ?
C9 C2 C1 120.0(2) . . ?
C3 C2 C1 119.5(2) . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C6 120.4(2) . . ?
C3 C4 C5 120.0(2) . . ?
C6 C4 C5 119.6(2) . . ?
O3 C5 O4 123.7(2) . . ?
O3 C5 C4 118.7(2) . . ?
O4 C5 C4 117.6(2) . . ?
C7 C6 C4 119.6(2) . . ?
C7 C6 H6 120.2 . . ?
C4 C6 H6 120.2 . . ?
O5 C7 C6 124.7(2) . . ?
O5 C7 C9 115.2(2) . . ?
C6 C7 C9 120.2(3) . . ?
O5 C8 H8A 109.5 . . ?
O5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C9 C7 120.0(2) . . ?
C2 C9 H9 120.0 . . ?
C7 C9 H9 120.0 . . ?
N1 C10 C11 123.2(4) . . ?
N1 C10 H10 118.4 . . ?
C11 C10 H10 118.4 . . ?
C10 C11 C12 118.8(4) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 118.4(4) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C14 C13 C12 118.9(4) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
N1 C14 C13 123.5(3) . . ?
N1 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
N2 C15 C16 123.4(3) . . ?
N2 C15 H15 118.3 . . ?
C16 C15 H15 118.3 . . ?
C15 C16 C17 119.2(4) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C18 C17 C16 117.7(4) . . ?
C18 C17 H17 121.1 . . ?
C16 C17 H17 121.1 . . ?
C19 C18 C17 120.3(4) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
N2 C19 C18 122.7(3) . . ?
N2 C19 H19 118.6 . . ?
C18 C19 H19 118.6 . . ?

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 O2 C1 O1 -1.7(3) . . . . ?
Co1 O2 C1 C2 177.8(2) . . . . ?
Co1 O1 C1 O2 1.8(3) . . . . ?
Co1 O1 C1 C2 -177.7(2) . . . . ?
O2 C1 C2 C9 -2.5(4) . . . . ?
O1 C1 C2 C9 177.0(3) . . . . ?
O2 C1 C2 C3 177.1(3) . . . . ?
O1 C1 C2 C3 -3.4(4) . . . . ?
C9 C2 C3 C4 -0.9(4) . . . . ?
C1 C2 C3 C4 179.4(2) . . . . ?
C2 C3 C4 C6 0.6(4) . . . . ?
C2 C3 C4 C5 -179.0(2) . . . . ?
Co1 O3 C5 O4 -73.0(12) 5_766 . . . ?
Co1 O3 C5 C4 107.5(10) 5_766 . . . ?
Co1 O4 C5 O3 1.8(4) 3_445 . . . ?
Co1 O4 C5 C4 -178.77(18) 3_445 . . . ?
C3 C4 C5 O3 -3.8(4) . . . . ?
C6 C4 C5 O3 176.6(3) . . . . ?
C3 C4 C5 O4 176.7(3) . . . . ?
C6 C4 C5 O4 -2.8(4) . . . . ?
C3 C4 C6 C7 -0.1(4) . . . . ?
C5 C4 C6 C7 179.5(2) . . . . ?
C8 O5 C7 C6 2.1(4) . . . . ?
C8 O5 C7 C9 -178.7(3) . . . . ?
C4 C6 C7 O5 179.0(3) . . . . ?
C4 C6 C7 C9 -0.1(4) . . . . ?
C3 C2 C9 C7 0.8(4) . . . . ?
C1 C2 C9 C7 -179.5(3) . . . . ?
O5 C7 C9 C2 -179.5(3) . . . . ?
C6 C7 C9 C2 -0.3(4) . . . . ?
C14 N1 C10 C11 -0.4(5) . . . . ?
Co1 N1 C10 C11 179.8(3) . . . . ?
N1 C10 C11 C12 0.6(6) . . . . ?
C10 C11 C12 C13 0.3(7) . . . . ?
C11 C12 C13 C14 -1.3(7) . . . . ?
C10 N1 C14 C13 -0.7(5) . . . . ?
Co1 N1 C14 C13 179.1(3) . . . . ?
C12 C13 C14 N1 1.6(6) . . . . ?
C19 N2 C15 C16 0.2(6) . . . . ?
Co1 N2 C15 C16 178.6(3) . . . . ?
N2 C15 C16 C17 -1.1(7) . . . . ?
C15 C16 C17 C18 1.2(8) . . . . ?
C16 C17 C18 C19 -0.4(8) . . . . ?
C15 N2 C19 C18 0.6(6) . . . . ?
Co1 N2 C19 C18 -177.8(3) . . . . ?
C17 C18 C19 N2 -0.5(7) . . . . ?

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
C19 H19 O4 0.93 2.58 3.100(5) 115.4 3
C16 H16 O5 0.93 2.55 3.221(4) 129.2 3_545
C13 H13 O2 0.93 2.51 3.231(5) 134.6 5_776
C10 H10 O3 0.93 2.51 3.048(5) 116.7 5_766
C19 H19 O4 0.93 2.58 3.100(5) 115.4 3
C16 H16 O5 0.93 2.55 3.221(4) 129.2 3_545
C15 H15 O3 0.93 2.67 3.133(5) 111.7 5_766
C13 H13 O2 0.93 2.51 3.231(5) 134.6 5_776
C10 H10 O3 0.93 2.51 3.048(5) 116.7 5_766
C10 H10 O3 0.93 2.51 3.048(5) 116.7 5_766
C13 H13 O2 0.93 2.51 3.231(5) 134.6 5_776
C16 H16 O5 0.93 2.55 3.221(4) 129.2 3_545
C19 H19 O4 0.93 2.58 3.100(5) 115.4 3

_refine_diff_density_max         0.499
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.103

####################################################################### 
# 
# 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_480-26Co3
_database_code_depnum_ccdc_archive 'CCDC 2269628'
_audit_update_record             
;
2023-06-13 deposited with the CCDC.	2023-08-01 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            'C19 H14 Co N2 O5'
_chemical_formula_weight         409.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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                   10.0273(10)
_cell_length_b                   10.0728(9)
_cell_length_c                   10.7050(14)
_cell_angle_alpha                74.711(9)
_cell_angle_beta                 66.547(11)
_cell_angle_gamma                76.120(8)
_cell_volume                     945.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5715
_cell_measurement_theta_min      4.585
_cell_measurement_theta_max      64.976

_exptl_crystal_description       needle
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_F_000             418
_exptl_transmission_factor_min   0.253
_exptl_transmission_factor_max   0.306
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    7.399
_shelx_estimated_absorpt_T_min   0.281
_shelx_estimated_absorpt_T_max   0.384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.281
_exptl_absorpt_correction_T_max  0.384
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5715
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.585
_diffrn_reflns_theta_max         64.976
_diffrn_reflns_theta_full        64.976
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3216
_reflns_number_gt                2712
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0944P)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_number_reflns         3216
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1439
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.56042(6) 0.61397(5) 0.59557(5) 0.0217(2) Uani 1 1 d . . . . .
N1 N 0.7521(3) 0.6121(3) 0.4118(3) 0.0265(7) Uani 1 1 d . . . . .
N2 N 1.3665(3) 0.6048(3) -0.2198(3) 0.0252(6) Uani 1 1 d . . . . .
O1 O 0.5725(3) 0.3384(3) 0.5165(3) 0.0315(6) Uani 1 1 d . . . . .
O2 O 0.6229(3) 0.4096(2) 0.6690(2) 0.0293(6) Uani 1 1 d . . . . .
O3 O 0.6685(3) -0.3199(2) 0.7112(3) 0.0364(6) Uani 1 1 d . . . . .
O4 O 0.5559(3) -0.1702(3) 0.5840(3) 0.0390(7) Uani 1 1 d . . . . .
O5 O 0.7483(7) -0.0333(4) 0.9842(5) 0.129(2) Uani 1 1 d . . . . .
C1 C 0.6097(4) 0.3159(3) 0.6196(3) 0.0244(7) Uani 1 1 d . . . . .
C2 C 0.6404(4) 0.1669(4) 0.6890(4) 0.0328(9) Uani 1 1 d . . . . .
C3 C 0.6206(4) 0.0585(4) 0.6439(4) 0.0304(8) Uani 1 1 d . . . . .
H3 H 0.5894 0.0770 0.5692 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6478(5) -0.0783(4) 0.7109(4) 0.0361(9) Uani 1 1 d . . . . .
C5 C 0.6244(4) -0.1968(4) 0.6659(4) 0.0302(8) Uani 1 1 d . . . . .
C6 C 0.6920(7) -0.1058(4) 0.8239(6) 0.0627(15) Uani 1 1 d . . . . .
H6 H 0.7108 -0.1972 0.8681 0.075 Uiso 1 1 calc R U . . .
C7 C 0.7083(7) 0.0036(5) 0.8711(6) 0.0682(18) Uani 1 1 d . . . . .
C8 C 0.6836(6) 0.1397(4) 0.8031(5) 0.0554(14) Uani 1 1 d . . . . .
H8 H 0.6958 0.2127 0.8336 0.066 Uiso 1 1 calc R U . . .
C9 C 0.7599(11) 0.0705(6) 1.0420(8) 0.133(4) Uani 1 1 d . . . . .
H9C H 0.8469 0.1110 0.9832 0.200 Uiso 1 1 calc R U . . .
H9A H 0.7657 0.0307 1.1320 0.200 Uiso 1 1 calc R U . . .
H9B H 0.6750 0.1412 1.0507 0.200 Uiso 1 1 calc R U . . .
C10 C 0.8765(4) 0.5209(4) 0.4048(4) 0.0368(9) Uani 1 1 d . . . . .
H10 H 0.8803 0.4586 0.4851 0.044 Uiso 1 1 calc R U . . .
C11 C 0.9975(4) 0.5149(4) 0.2859(4) 0.0393(10) Uani 1 1 d . . . . .
H11 H 1.0811 0.4508 0.2875 0.047 Uiso 1 1 calc R U . . .
C12 C 0.9959(4) 0.6047(4) 0.1624(4) 0.0265(8) Uani 1 1 d . . . . .
C13 C 0.8684(4) 0.6981(4) 0.1707(4) 0.0412(10) Uani 1 1 d . . . . .
H13 H 0.8607 0.7604 0.0916 0.049 Uiso 1 1 calc R U . . .
C14 C 0.7528(4) 0.6999(4) 0.2947(4) 0.0426(11) Uani 1 1 d . . . . .
H14 H 0.6701 0.7665 0.2969 0.051 Uiso 1 1 calc R U . . .
C15 C 1.1218(4) 0.6021(4) 0.0305(4) 0.0264(8) Uani 1 1 d . . . . .
C16 C 1.2598(4) 0.5273(4) 0.0262(4) 0.0374(9) Uani 1 1 d . . . . .
H16 H 1.2734 0.4754 0.1072 0.045 Uiso 1 1 calc R U . . .
C17 C 1.3754(4) 0.5309(4) -0.0987(4) 0.0367(9) Uani 1 1 d . . . . .
H17 H 1.4656 0.4786 -0.0991 0.044 Uiso 1 1 calc R U . . .
C18 C 1.2332(4) 0.6731(4) -0.2162(4) 0.0374(9) Uani 1 1 d . . . . .
H18 H 1.2224 0.7225 -0.2992 0.045 Uiso 1 1 calc R U . . .
C19 C 1.1122(4) 0.6741(5) -0.0971(4) 0.0399(10) Uani 1 1 d . . . . .
H19 H 1.0223 0.7234 -0.1010 0.048 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 O1 2.028(3) 2_666 ?
Co1 O2 2.041(2) . ?
Co1 N1 2.135(3) . ?
Co1 O4 2.136(3) 1_565 ?
Co1 N2 2.151(3) 1_456 ?
Co1 O3 2.236(3) 1_565 ?
Co1 C5 2.518(4) 1_565 ?
N1 C14 1.328(5) . ?
N1 C10 1.348(5) . ?
N2 C18 1.339(5) . ?
N2 C17 1.339(5) . ?
N2 Co1 2.151(3) 1_654 ?
O1 C1 1.250(4) . ?
O1 Co1 2.028(3) 2_666 ?
O2 C1 1.252(4) . ?
O3 C5 1.248(4) . ?
O3 Co1 2.236(3) 1_545 ?
O4 C5 1.257(5) . ?
O4 Co1 2.136(3) 1_545 ?
O5 C7 1.358(5) . ?
O5 C9 1.394(6) . ?
C1 C2 1.507(5) . ?
C2 C3 1.387(5) . ?
C2 C8 1.393(6) . ?
C3 C4 1.394(5) . ?
C3 H3 0.9300 . ?
C4 C6 1.388(6) . ?
C4 C5 1.496(5) . ?
C5 Co1 2.518(4) 1_545 ?
C6 C7 1.393(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.388(6) . ?
C8 H8 0.9300 . ?
C9 H9C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C10 C11 1.368(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(5) . ?
C12 C15 1.474(5) . ?
C13 C14 1.372(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C19 1.396(5) . ?
C15 C16 1.396(5) . ?
C16 C17 1.376(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.367(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

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 O2 118.93(10) 2_666 . ?
O1 Co1 N1 91.33(11) 2_666 . ?
O2 Co1 N1 91.07(10) . . ?
O1 Co1 O4 90.86(10) 2_666 1_565 ?
O2 Co1 O4 150.08(11) . 1_565 ?
N1 Co1 O4 90.86(11) . 1_565 ?
O1 Co1 N2 88.14(11) 2_666 1_456 ?
O2 Co1 N2 86.55(10) . 1_456 ?
N1 Co1 N2 176.93(11) . 1_456 ?
O4 Co1 N2 92.17(11) 1_565 1_456 ?
O1 Co1 O3 150.04(10) 2_666 1_565 ?
O2 Co1 O3 90.49(10) . 1_565 ?
N1 Co1 O3 93.79(11) . 1_565 ?
O4 Co1 O3 59.60(9) 1_565 1_565 ?
N2 Co1 O3 88.17(11) 1_456 1_565 ?
O1 Co1 C5 120.54(11) 2_666 1_565 ?
O2 Co1 C5 120.17(11) . 1_565 ?
N1 Co1 C5 93.49(12) . 1_565 ?
O4 Co1 C5 29.92(11) 1_565 1_565 ?
N2 Co1 C5 89.38(11) 1_456 1_565 ?
O3 Co1 C5 29.70(11) 1_565 1_565 ?
C14 N1 C10 115.9(3) . . ?
C14 N1 Co1 120.8(2) . . ?
C10 N1 Co1 123.2(2) . . ?
C18 N2 C17 116.1(3) . . ?
C18 N2 Co1 123.7(2) . 1_654 ?
C17 N2 Co1 120.2(2) . 1_654 ?
C1 O1 Co1 159.0(2) . 2_666 ?
C1 O2 Co1 120.2(2) . . ?
C5 O3 Co1 87.8(2) . 1_545 ?
C5 O4 Co1 92.1(2) . 1_545 ?
C7 O5 C9 119.3(4) . . ?
O1 C1 O2 124.0(3) . . ?
O1 C1 C2 118.1(3) . . ?
O2 C1 C2 117.9(3) . . ?
C3 C2 C8 120.2(4) . . ?
C3 C2 C1 120.8(3) . . ?
C8 C2 C1 118.9(3) . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C6 C4 C3 120.2(4) . . ?
C6 C4 C5 119.1(4) . . ?
C3 C4 C5 120.7(3) . . ?
O3 C5 O4 120.4(3) . . ?
O3 C5 C4 121.0(3) . . ?
O4 C5 C4 118.6(3) . . ?
O3 C5 Co1 62.53(19) . 1_545 ?
O4 C5 Co1 57.95(18) . 1_545 ?
C4 C5 Co1 174.7(3) . 1_545 ?
C4 C6 C7 120.0(4) . . ?
C4 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
O5 C7 C8 124.3(4) . . ?
O5 C7 C6 115.8(4) . . ?
C8 C7 C6 119.9(4) . . ?
C7 C8 C2 120.0(4) . . ?
C7 C8 H8 120.0 . . ?
C2 C8 H8 120.0 . . ?
O5 C9 H9C 109.5 . . ?
O5 C9 H9A 109.5 . . ?
H9C C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
H9C C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C10 C11 123.6(3) . . ?
N1 C10 H10 118.2 . . ?
C11 C10 H10 118.2 . . ?
C10 C11 C12 120.1(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 115.8(3) . . ?
C13 C12 C15 121.4(3) . . ?
C11 C12 C15 122.8(3) . . ?
C14 C13 C12 120.5(4) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
N1 C14 C13 123.9(4) . . ?
N1 C14 H14 118.0 . . ?
C13 C14 H14 118.0 . . ?
C19 C15 C16 115.7(3) . . ?
C19 C15 C12 122.8(3) . . ?
C16 C15 C12 121.5(3) . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
N2 C17 C16 124.2(3) . . ?
N2 C17 H17 117.9 . . ?
C16 C17 H17 117.9 . . ?
N2 C18 C19 123.4(3) . . ?
N2 C18 H18 118.3 . . ?
C19 C18 H18 118.3 . . ?
C18 C19 C15 120.8(4) . . ?
C18 C19 H19 119.6 . . ?
C15 C19 H19 119.6 . . ?

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 O1 C1 O2 -81.9(7) 2_666 . . . ?
Co1 O1 C1 C2 98.0(7) 2_666 . . . ?
Co1 O2 C1 O1 7.1(5) . . . . ?
Co1 O2 C1 C2 -172.8(2) . . . . ?
O1 C1 C2 C3 -3.2(5) . . . . ?
O2 C1 C2 C3 176.7(3) . . . . ?
O1 C1 C2 C8 179.3(4) . . . . ?
O2 C1 C2 C8 -0.8(6) . . . . ?
C8 C2 C3 C4 -1.6(7) . . . . ?
C1 C2 C3 C4 -179.1(3) . . . . ?
C2 C3 C4 C6 1.1(7) . . . . ?
C2 C3 C4 C5 178.8(4) . . . . ?
Co1 O3 C5 O4 -2.8(4) 1_545 . . . ?
Co1 O3 C5 C4 175.4(3) 1_545 . . . ?
Co1 O4 C5 O3 2.9(4) 1_545 . . . ?
Co1 O4 C5 C4 -175.3(3) 1_545 . . . ?
C6 C4 C5 O3 -12.9(7) . . . . ?
C3 C4 C5 O3 169.4(4) . . . . ?
C6 C4 C5 O4 165.3(4) . . . . ?
C3 C4 C5 O4 -12.4(6) . . . . ?
C3 C4 C6 C7 0.4(8) . . . . ?
C5 C4 C6 C7 -177.3(5) . . . . ?
C9 O5 C7 C8 3.0(12) . . . . ?
C9 O5 C7 C6 -176.9(8) . . . . ?
C4 C6 C7 O5 178.4(6) . . . . ?
C4 C6 C7 C8 -1.5(10) . . . . ?
O5 C7 C8 C2 -178.9(6) . . . . ?
C6 C7 C8 C2 0.9(10) . . . . ?
C3 C2 C8 C7 0.6(8) . . . . ?
C1 C2 C8 C7 178.2(5) . . . . ?
C14 N1 C10 C11 -0.8(6) . . . . ?
Co1 N1 C10 C11 177.0(3) . . . . ?
N1 C10 C11 C12 -1.1(7) . . . . ?
C10 C11 C12 C13 1.3(6) . . . . ?
C10 C11 C12 C15 -179.1(4) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C15 C12 C13 C14 -179.3(4) . . . . ?
C10 N1 C14 C13 2.5(6) . . . . ?
Co1 N1 C14 C13 -175.4(4) . . . . ?
C12 C13 C14 N1 -2.2(7) . . . . ?
C13 C12 C15 C19 -11.8(6) . . . . ?
C11 C12 C15 C19 168.6(4) . . . . ?
C13 C12 C15 C16 167.7(4) . . . . ?
C11 C12 C15 C16 -11.9(6) . . . . ?
C19 C15 C16 C17 1.4(6) . . . . ?
C12 C15 C16 C17 -178.2(4) . . . . ?
C18 N2 C17 C16 -3.2(6) . . . . ?
Co1 N2 C17 C16 175.0(3) 1_654 . . . ?
C15 C16 C17 N2 1.3(7) . . . . ?
C17 N2 C18 C19 2.5(6) . . . . ?
Co1 N2 C18 C19 -175.7(3) 1_654 . . . ?
N2 C18 C19 C15 0.1(7) . . . . ?
C16 C15 C19 C18 -2.0(6) . . . . ?
C12 C15 C19 C18 177.5(4) . . . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 132 13 ' '
_platon_squeeze_details          
;
;

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
C18 H18 O1 0.93 2.52 3.041(4) 115.6 2_765
C17 H17 O2 0.93 2.53 3.011(5) 112.5 1_654
C16 H16 O3 0.93 2.33 3.253(5) 171.0 2_756
C13 H13 O5 0.93 2.36 3.203(5) 150.9 1_564
C11 H11 O3 0.93 2.54 3.459(5) 168.0 2_756
C10 H10 O2 0.93 2.61 3.114(5) 114.3 .
C18 H18 O1 0.93 2.52 3.041(4) 115.6 2_765
C17 H17 O2 0.93 2.53 3.011(5) 112.5 1_654
C16 H16 O3 0.93 2.33 3.253(5) 171.0 2_756
C13 H13 O5 0.93 2.36 3.203(5) 150.9 1_564
C11 H11 O3 0.93 2.54 3.459(5) 168.0 2_756
C10 H10 O2 0.93 2.61 3.114(5) 114.3 .
C18 H18 O1 0.93 2.52 3.041(4) 115.6 2_765
C17 H17 O2 0.93 2.53 3.011(5) 112.5 1_654
C16 H16 O3 0.93 2.33 3.253(5) 171.0 2_756
C13 H13 O5 0.93 2.36 3.203(5) 150.9 1_564
C11 H11 O3 0.93 2.54 3.459(5) 168.0 2_756
C10 H10 O2 0.93 2.61 3.114(5) 114.3 .
C10 H10 O2 0.93 2.61 3.114(5) 114.3 .
C11 H11 O3 0.93 2.54 3.459(5) 168.0 2_756
C13 H13 O5 0.93 2.36 3.203(5) 150.9 1_564
C16 H16 O3 0.93 2.33 3.253(5) 171.0 2_756
C17 H17 O2 0.93 2.53 3.011(5) 112.5 1_654
C18 H18 O1 0.93 2.52 3.041(4) 115.6 2_765
C10 H10 O2 0.93 2.61 3.114(5) 114.3 .
C11 H11 O3 0.93 2.54 3.459(5) 168.0 2_756
C13 H13 O5 0.93 2.36 3.203(5) 150.9 1_564
C16 H16 O3 0.93 2.33 3.253(5) 171.0 2_756
C17 H17 O2 0.93 2.53 3.011(5) 112.5 1_654
C18 H18 O1 0.93 2.52 3.041(4) 115.6 2_765

_refine_diff_density_max         1.241
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.100

