# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

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

data_1Co
_database_code_depnum_ccdc_archive 'CCDC 1968824'
loop_
_audit_author_name
_audit_author_address
'Stuart Batten'
;Monash University
Australia
;
_audit_update_record             
;
2020-03-14 deposited with the CCDC.	2020-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H33 Co N2 O12.50'
_chemical_formula_sum            'C23 H33 Co N2 O12.50'
_chemical_formula_weight         596.44

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   19.850(4)
_cell_length_b                   9.2680(19)
_cell_length_c                   14.146(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2602.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7506
_cell_measurement_theta_min      2.052
_cell_measurement_theta_max      31.804

_exptl_crystal_description       Plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   0.6989
_exptl_transmission_factor_max   0.7463
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.729
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42785
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.052
_diffrn_reflns_theta_max         31.804
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             7506
_reflns_number_gt                6652
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_max     0.829
_reflns_Friedel_fraction_full    0.986

_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       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0497P)²+1.3853P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2879 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7506
_refine_ls_number_parameters     369
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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 0.10597(2) 0.28150(4) 0.29443(3) 0.01344(9) Uani 1 1 d . . . . .
O1 O 1.01557(12) 0.3099(2) 0.35960(18) 0.0171(4) Uani 1 1 d . . . . .
O2 O 1.06453(12) 0.1034(3) 0.39428(18) 0.0189(5) Uani 1 1 d . . . . .
O3 O 0.95838(13) -0.1761(3) 0.66899(19) 0.0205(5) Uani 1 1 d . . . . .
O4 O 0.85371(12) -0.1249(3) 0.70849(18) 0.0187(5) Uani 1 1 d . . . . .
O5 O 0.45544(12) 0.5925(3) 0.62866(18) 0.0207(5) Uani 1 1 d . . . . .
O6 O 0.38411(13) 0.4667(3) 0.71822(17) 0.0181(5) Uani 1 1 d . . . . .
O7 O 0.18831(12) 0.3279(3) 0.36937(18) 0.0196(5) Uani 1 1 d . . . . .
O8 O 0.17846(12) 0.2825(3) 0.52410(19) 0.0222(5) Uani 1 1 d . . . . .
N1 N 0.72360(14) 0.1868(3) 0.4016(2) 0.0180(5) Uani 1 1 d . . . . .
H1 H 0.744438 0.198895 0.337769 0.022 Uiso 1 1 calc R U . . .
N2 N 0.48880(13) 0.2901(3) 0.2810(2) 0.0155(5) Uani 1 1 d . . . . .
H2 H 0.512407 0.314404 0.220588 0.019 Uiso 1 1 calc R U . . .
C1 C 0.46076(17) 0.1425(4) 0.2683(3) 0.0210(7) Uani 1 1 d . . . . .
H1A H 0.497545 0.074604 0.255831 0.031 Uiso 1 1 calc R U . . .
H1B H 0.429380 0.142258 0.214786 0.031 Uiso 1 1 calc R U . . .
H1C H 0.436869 0.113469 0.325836 0.031 Uiso 1 1 calc R U . . .
C2 C 0.54105(17) 0.2991(4) 0.3575(2) 0.0179(6) Uani 1 1 d . . . . .
H2A H 0.522946 0.254826 0.415910 0.021 Uiso 1 1 calc R U . . .
H2B H 0.550765 0.401771 0.371091 0.021 Uiso 1 1 calc R U . . .
C3 C 0.60662(16) 0.2227(4) 0.3301(3) 0.0194(6) Uani 1 1 d . . . . .
H3A H 0.600553 0.116670 0.331179 0.023 Uiso 1 1 calc R U . . .
H3B H 0.621092 0.251968 0.265966 0.023 Uiso 1 1 calc R U . . .
C4 C 0.65816(18) 0.2687(4) 0.4031(3) 0.0258(8) Uani 1 1 d . . . . .
H4A H 0.668115 0.372364 0.393551 0.031 Uiso 1 1 calc R U . . .
H4B H 0.637804 0.258286 0.466610 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7136(2) 0.0292(4) 0.4190(4) 0.0338(10) Uani 1 1 d . . . . .
H5A H 0.757402 -0.019661 0.418892 0.051 Uiso 1 1 calc R U . . .
H5B H 0.685140 -0.011441 0.369018 0.051 Uiso 1 1 calc R U . . .
H5C H 0.691729 0.015198 0.480410 0.051 Uiso 1 1 calc R U . . .
C6 C 0.76973(17) 0.2561(3) 0.4740(3) 0.0191(6) Uani 1 1 d . . . . .
H6A H 0.779522 0.356123 0.453648 0.023 Uiso 1 1 calc R U . . .
H6B H 0.745535 0.261606 0.535133 0.023 Uiso 1 1 calc R U . . .
C7 C 0.83548(16) 0.1787(3) 0.4895(2) 0.0168(6) Uani 1 1 d . . . . .
C8 C 0.84059(16) 0.0765(4) 0.5619(2) 0.0171(6) Uani 1 1 d . . . . .
H8 H 0.802407 0.055704 0.599985 0.020 Uiso 1 1 calc R U . . .
C9 C 0.90116(17) 0.0048(4) 0.5786(2) 0.0164(6) Uani 1 1 d . . . . .
C10 C 0.90525(16) -0.1052(4) 0.6556(2) 0.0168(6) Uani 1 1 d . . . . .
C11 C 0.95776(16) 0.0388(3) 0.5248(2) 0.0156(6) Uani 1 1 d . . . . .
H11 H 0.999130 -0.009835 0.535935 0.019 Uiso 1 1 calc R U . . .
C12 C 0.95376(15) 0.1442(3) 0.4544(2) 0.0155(6) Uani 1 1 d . . . . .
C13 C 1.01515(17) 0.1867(3) 0.4001(2) 0.0162(6) Uani 1 1 d . . . . .
C14 C 0.89200(16) 0.2117(3) 0.4364(2) 0.0160(6) Uani 1 1 d . . . . .
H14 H 0.888834 0.281059 0.387197 0.019 Uiso 1 1 calc R U . . .
C15 C 0.43343(14) 0.4016(3) 0.2927(3) 0.0163(5) Uani 1 1 d . . . . .
H15A H 0.454051 0.498776 0.290812 0.020 Uiso 1 1 calc R U . . .
H15B H 0.402363 0.393964 0.238223 0.020 Uiso 1 1 calc R U . . .
C16 C 0.39280(16) 0.3886(3) 0.3825(2) 0.0157(6) Uani 1 1 d . . . . .
C17 C 0.32645(16) 0.3409(3) 0.3791(2) 0.0161(6) Uani 1 1 d . . . . .
H17 H 0.308180 0.307257 0.321115 0.019 Uiso 1 1 calc R U . . .
C18 C 0.28639(15) 0.3420(3) 0.4604(2) 0.0150(6) Uani 1 1 d . . . . .
C19 C 0.21173(16) 0.3125(3) 0.4519(2) 0.0159(6) Uani 1 1 d . . . . .
C20 C 0.31394(16) 0.3849(3) 0.5472(2) 0.0148(6) Uani 1 1 d . . . . .
H20 H 0.288047 0.378690 0.603543 0.018 Uiso 1 1 calc R U . . .
C21 C 0.38018(16) 0.4371(3) 0.5498(2) 0.0151(6) Uani 1 1 d . . . . .
C22 C 0.40888(16) 0.5009(3) 0.6389(2) 0.0153(6) Uani 1 1 d . . . . .
C23 C 0.41848(15) 0.4413(3) 0.4677(2) 0.0143(5) Uani 1 1 d . . . . .
H23 H 0.462690 0.480411 0.469480 0.017 Uiso 1 1 calc R U . . .
O9 O 0.21328(13) 0.1346(3) 0.6853(2) 0.0271(6) Uani 1 1 d G . . . .
H9A H 0.256098 0.134339 0.684718 0.041 Uiso 1 1 d G U . . .
H9B H 0.202323 0.191596 0.640798 0.041 Uiso 1 1 d G U . . .
O10 O 0.08030(14) 0.4841(3) 0.5518(2) 0.0313(6) Uani 1 1 d G . . . .
H10A H 0.041790 0.452161 0.567741 0.047 Uiso 1 1 d G U . . .
H10B H 0.106025 0.413706 0.538405 0.047 Uiso 1 1 d G U . . .
O11 O 0.09499(19) 0.7398(5) 0.6492(4) 0.0628(14) Uani 1 1 d G . . . .
H11A H 0.056416 0.776333 0.659707 0.094 Uiso 1 1 d G U . . .
H11B H 0.086758 0.663065 0.618348 0.094 Uiso 1 1 d G U . . .
O12 O 0.20854(17) 0.8441(4) 0.7317(3) 0.0412(8) Uani 1 1 d G . . . .
H12A H 0.174321 0.816710 0.700428 0.062 Uiso 1 1 d G U . . .
H12B H 0.206954 0.935728 0.729540 0.062 Uiso 1 1 d G U . . .
O13 O 0.7549(6) 0.4196(15) 0.2656(9) 0.092(4) Uani 0.5 1 d G . P A 1
H13A H 0.717460 0.413359 0.236849 0.138 Uiso 0.5 1 d G U P A 1
H13B H 0.779851 0.357025 0.238986 0.138 Uiso 0.5 1 d G U P A 1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O7 1.995(2) . ?
Co1 O1 2.035(2) 1_455 ?
Co1 O6 2.037(2) 4_554 ?
Co1 O4 2.055(2) 2_654 ?
Co1 O2 2.323(2) 1_455 ?
Co1 O3 2.395(3) 2_654 ?
O1 C13 1.277(4) . ?
O2 C13 1.251(4) . ?
O3 C10 1.257(4) . ?
O4 C10 1.280(4) . ?
O5 C22 1.263(4) . ?
O6 C22 1.265(4) . ?
O7 C19 1.265(4) . ?
O8 C19 1.247(4) . ?
N1 C5 1.495(5) . ?
N1 C4 1.505(4) . ?
N1 C6 1.517(4) . ?
N2 C1 1.487(4) . ?
N2 C2 1.502(4) . ?
N2 C15 1.518(4) . ?
C2 C3 1.531(5) . ?
C3 C4 1.514(5) . ?
C6 C7 1.505(4) . ?
C7 C14 1.384(5) . ?
C7 C8 1.398(5) . ?
C8 C9 1.394(5) . ?
C9 C11 1.393(5) . ?
C9 C10 1.495(5) . ?
C11 C12 1.397(4) . ?
C12 C14 1.400(4) . ?
C12 C13 1.494(4) . ?
C15 C16 1.509(5) . ?
C16 C17 1.390(4) . ?
C16 C23 1.396(4) . ?
C17 C18 1.397(4) . ?
C18 C20 1.402(5) . ?
C18 C19 1.512(4) . ?
C20 C21 1.402(4) . ?
C21 C23 1.389(5) . ?
C21 C22 1.505(5) . ?

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
O7 Co1 O1 116.99(11) . 1_455 ?
O7 Co1 O6 91.17(10) . 4_554 ?
O1 Co1 O6 102.47(10) 1_455 4_554 ?
O7 Co1 O4 98.48(10) . 2_654 ?
O1 Co1 O4 134.66(10) 1_455 2_654 ?
O6 Co1 O4 104.14(10) 4_554 2_654 ?
O7 Co1 O2 96.90(10) . 1_455 ?
O1 Co1 O2 60.28(9) 1_455 1_455 ?
O6 Co1 O2 162.75(9) 4_554 1_455 ?
O4 Co1 O2 89.76(9) 2_654 1_455 ?
O7 Co1 O3 156.74(10) . 2_654 ?
O1 Co1 O3 85.30(9) 1_455 2_654 ?
O6 Co1 O3 90.17(9) 4_554 2_654 ?
O4 Co1 O3 58.77(9) 2_654 2_654 ?
O2 Co1 O3 88.39(9) 1_455 2_654 ?
O7 Co1 C13 110.42(11) . 1_455 ?
O1 Co1 C13 30.56(10) 1_455 1_455 ?
O6 Co1 C13 132.99(11) 4_554 1_455 ?
O4 Co1 C13 112.72(10) 2_654 1_455 ?
O2 Co1 C13 29.76(9) 1_455 1_455 ?
O3 Co1 C13 85.11(10) 2_654 1_455 ?
C13 O1 Co1 95.3(2) . 1_655 ?
C13 O2 Co1 83.0(2) . 1_655 ?
C10 O3 Co1 82.9(2) . 2_655 ?
C10 O4 Co1 97.8(2) . 2_655 ?
C22 O6 Co1 130.0(2) . 4 ?
C19 O7 Co1 140.1(2) . . ?
C5 N1 C4 112.1(3) . . ?
C5 N1 C6 112.5(3) . . ?
C4 N1 C6 107.4(3) . . ?
C1 N2 C2 113.4(3) . . ?
C1 N2 C15 111.6(2) . . ?
C2 N2 C15 112.5(3) . . ?
N2 C2 C3 112.3(3) . . ?
C4 C3 C2 105.8(3) . . ?
N1 C4 C3 115.6(3) . . ?
C7 C6 N1 114.8(3) . . ?
C14 C7 C8 119.2(3) . . ?
C14 C7 C6 121.2(3) . . ?
C8 C7 C6 119.5(3) . . ?
C9 C8 C7 120.6(3) . . ?
C11 C9 C8 119.7(3) . . ?
C11 C9 C10 120.6(3) . . ?
C8 C9 C10 119.7(3) . . ?
O3 C10 O4 120.5(3) . . ?
O3 C10 C9 120.8(3) . . ?
O4 C10 C9 118.7(3) . . ?
C9 C11 C12 120.1(3) . . ?
C11 C12 C14 119.5(3) . . ?
C11 C12 C13 120.3(3) . . ?
C14 C12 C13 120.2(3) . . ?
O2 C13 O1 121.2(3) . . ?
O2 C13 C12 120.7(3) . . ?
O1 C13 C12 118.1(3) . . ?
O2 C13 Co1 67.22(18) . 1_655 ?
O1 C13 Co1 54.10(16) . 1_655 ?
C12 C13 Co1 171.2(2) . 1_655 ?
C7 C14 C12 120.8(3) . . ?
C16 C15 N2 115.2(3) . . ?
C17 C16 C23 119.1(3) . . ?
C17 C16 C15 120.2(3) . . ?
C23 C16 C15 120.2(3) . . ?
C16 C17 C18 120.6(3) . . ?
C17 C18 C20 120.0(3) . . ?
C17 C18 C19 119.5(3) . . ?
C20 C18 C19 120.2(3) . . ?
O8 C19 O7 125.9(3) . . ?
O8 C19 C18 119.7(3) . . ?
O7 C19 C18 114.4(3) . . ?
C21 C20 C18 119.1(3) . . ?
C23 C21 C20 120.1(3) . . ?
C23 C21 C22 118.9(3) . . ?
C20 C21 C22 120.8(3) . . ?
O5 C22 O6 123.7(3) . . ?
O5 C22 C21 116.4(3) . . ?
O6 C22 C21 119.8(3) . . ?
C21 C23 C16 120.8(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O12 1.00 1.81 2.770(5) 159.5 2_664 yes
N1 H1 O13 1.00 2.30 2.957(15) 122.6 . yes
N2 H2 O5 1.00 1.69 2.656(4) 162.1 2_664 yes
O9 H9A O4 0.85 1.97 2.808(4) 169.4 3_455 yes
O9 H9B O8 0.85 1.91 2.748(4) 167.4 . yes
O10 H10A O5 0.85 1.96 2.798(4) 167.2 3_465 yes
O10 H10B O8 0.85 1.89 2.728(4) 166.6 . yes
O11 H11A O3 0.85 2.00 2.835(5) 167.3 1_465 yes
O11 H11B O10 0.85 1.91 2.756(5) 172.5 . yes
O12 H12A O11 0.85 1.87 2.717(5) 170.7 . yes
O12 H12B O9 0.85 1.95 2.773(5) 162.4 1_565 yes
O13 H13A O6 0.85 2.32 3.030(12) 141.6 2_664 yes
O13 H13B O12 0.85 1.88 2.594(13) 140.4 2_664 yes

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.999
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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_1Zn
_database_code_depnum_ccdc_archive 'CCDC 1968825'
loop_
_audit_author_name
_audit_author_address
'Stuart Batten'
;Monash University
Australia
;
_audit_update_record             
;
2020-03-14 deposited with the CCDC.	2020-03-23 downloaded from the CCDC.
;

_audit_creation_date             2020-03-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 N2 O8 Zn, 4.5(H2 O)'
_chemical_formula_sum            'C23 H33 N2 O12.50 Zn'
_chemical_formula_weight         602.88
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn1 C20 H21 N2 O12'
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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   19.8716(4)
_cell_length_b                   9.3173(2)
_cell_length_c                   14.1140(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2613.20(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4576
_cell_measurement_temperature    123.00(13)
_cell_measurement_theta_max      75.8750
_cell_measurement_theta_min      4.4530
_shelx_estimated_absorpt_T_max   0.831
_shelx_estimated_absorpt_T_min   0.597
_exptl_absorpt_coefficient_mu    1.917
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14457
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.239
_diffrn_reflns_theta_min         4.450
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00  24.00   0.50    1.93    --  -48.53  37.00  60.00  164
  2  ω     43.00  98.00   0.50    1.93    --   48.53-135.00  54.00  110
  3  ω     96.00 124.00   0.50    7.72    --  105.75-135.00  54.00   56
  4  ω     41.00 116.00   0.50    7.72    --  105.75 -61.00 -90.00  150
  5  ω     76.00 107.00   0.50    7.72    --  105.75 -94.00-120.00   62
  6  ω     45.00  75.00   0.50    7.72    --  105.75 -45.00 -90.00   60
  7  ω     36.00  64.00   0.50    7.72    --  105.75 -30.00 -60.00   56
  8  ω     34.00  59.00   0.50    7.72    --  105.75 -45.00   0.00   50
  9  ω     34.00 153.00   0.50    7.72    --  105.75  -2.00  81.00  238
 10  ω     88.00 178.00   0.50    7.72    --  105.75 132.00  32.00  180
 11  ω     36.00  68.00   0.50    7.72    --  105.75 -94.00-120.00   64
 12  ω     36.00 123.00   0.50    7.72    --  105.75-134.00-126.00  174
 13  ω   -120.00  -1.00   0.50    1.93    --  -48.53  -2.00  81.00  238
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0774380000
_diffrn_orient_matrix_UB_12      -0.0040165000
_diffrn_orient_matrix_UB_13      -0.0045143000
_diffrn_orient_matrix_UB_21      0.0032816000
_diffrn_orient_matrix_UB_22      0.0010332000
_diffrn_orient_matrix_UB_23      -0.1090674000
_diffrn_orient_matrix_UB_31      0.0019343000
_diffrn_orient_matrix_UB_32      -0.1652639000
_diffrn_orient_matrix_UB_33      -0.0005349000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.610
_reflns_Friedel_fraction_full    0.709
_reflns_Friedel_fraction_max     0.648
_reflns_number_gt                4026
_reflns_number_total             4541
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.354
_refine_diff_density_min         -1.253
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details 
;
 Flack x determined using 1364 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         4541
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0723P)²+4.7594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1551
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O8-H10B
 1.894 with sigma of 0.001
 O4_$2-H9A_$4
 1.963 with sigma of 0.001
 O6-H13B
 2.248 with sigma of 0.001
 H13A-O12
 1.822 with sigma of 0.001
3. Others
 Fixed Sof: O13(0.5) H13A(0.5) H13B(0.5)
4.a Free rotating group:
 O10(H10A,H10B), O11(H11A,H11B), O12(H12A,H12B), O13(H13A,H13B)
4.b Ternary CH refined with riding coordinates:
 N1(H1), N2(H2)
4.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C15(H15A,H15B)
4.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C14(H14), C17(H17), C20(H20), C23(H23)
4.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.89086(4) 0.71392(8) 0.27940(9) 0.0150(2) Uani 1 1 d . . . . .
O1 O -0.0202(2) 0.6897(5) 0.3466(4) 0.0201(12) Uani 1 1 d . . . . .
O2 O -0.0649(3) 0.9007(5) 0.3755(4) 0.0226(12) Uani 1 1 d . . . . .
O3 O 0.0356(3) 1.1737(6) 0.6484(5) 0.0249(13) Uani 1 1 d . . . . .
O4 O 0.1421(2) 1.1366(5) 0.6864(4) 0.0189(11) Uani 1 1 d . . . . .
O5 O 0.5440(3) 0.4063(5) 0.6116(4) 0.0214(11) Uani 1 1 d . . . . .
O6 O 0.6147(2) 0.5301(5) 0.7021(4) 0.0196(11) Uani 1 1 d D . . . .
O7 O 0.8065(3) 0.6729(6) 0.3487(4) 0.0220(12) Uani 1 1 d . . . . .
O8 O 0.8196(3) 0.7160(5) 0.5031(4) 0.0222(11) Uani 1 1 d D . . . .
N1 N 0.2741(3) 0.8161(6) 0.3869(5) 0.0183(13) Uani 1 1 d . . . . .
H1 H 0.254262 0.805060 0.323697 0.022 Uiso 1 1 calc R U . . .
N2 N 0.5082(3) 0.7113(6) 0.2657(5) 0.0184(14) Uani 1 1 d . . . . .
H2 H 0.484763 0.688505 0.206471 0.022 Uiso 1 1 calc R U . . .
C1 C 0.5376(4) 0.8570(7) 0.2533(6) 0.0220(18) Uani 1 1 d . . . . .
H1A H 0.502144 0.924877 0.241856 0.033 Uiso 1 1 calc R U . . .
H1B H 0.567895 0.856417 0.200325 0.033 Uiso 1 1 calc R U . . .
H1C H 0.561603 0.883604 0.309580 0.033 Uiso 1 1 calc R U . . .
C2 C 0.4564(3) 0.7040(8) 0.3426(6) 0.0186(15) Uani 1 1 d . . . . .
H2A H 0.474284 0.748971 0.399278 0.022 Uiso 1 1 calc R U . . .
H2B H 0.447295 0.604179 0.357327 0.022 Uiso 1 1 calc R U . . .
C3 C 0.3904(3) 0.7783(8) 0.3150(6) 0.0200(16) Uani 1 1 d . . . . .
H3A H 0.396151 0.881691 0.314085 0.024 Uiso 1 1 calc R U . . .
H3B H 0.375755 0.747080 0.252804 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3396(4) 0.7353(8) 0.3897(7) 0.0240(17) Uani 1 1 d . . . . .
H4A H 0.330121 0.633764 0.382652 0.029 Uiso 1 1 calc R U . . .
H4B H 0.359825 0.748950 0.451609 0.029 Uiso 1 1 calc R U . . .
C5 C 0.2848(5) 0.9720(8) 0.4055(9) 0.040(3) Uani 1 1 d . . . . .
H5A H 0.306069 0.984051 0.466017 0.060 Uiso 1 1 calc R U . . .
H5B H 0.242195 1.020594 0.405458 0.060 Uiso 1 1 calc R U . . .
H5C H 0.313026 1.011765 0.356901 0.060 Uiso 1 1 calc R U . . .
C6 C 0.2280(4) 0.7465(8) 0.4584(7) 0.0211(16) Uani 1 1 d . . . . .
H6A H 0.251417 0.740642 0.518607 0.025 Uiso 1 1 calc R U . . .
H6B H 0.218492 0.649285 0.437897 0.025 Uiso 1 1 calc R U . . .
C7 C 0.1618(3) 0.8244(7) 0.4736(5) 0.0152(15) Uani 1 1 d . . . . .
C8 C 0.1567(3) 0.9262(7) 0.5443(6) 0.0191(15) Uani 1 1 d . . . . .
H8 H 0.194149 0.947775 0.581223 0.023 Uiso 1 1 calc R U . . .
C9 C 0.0956(4) 0.9976(8) 0.5611(6) 0.0175(15) Uani 1 1 d . . . . .
C10 C 0.0905(4) 1.1102(7) 0.6365(6) 0.0189(15) Uani 1 1 d . . . . .
C11 C 0.0401(3) 0.9610(7) 0.5057(6) 0.0164(14) Uani 1 1 d . . . . .
H11 H -0.000481 1.008496 0.515267 0.020 Uiso 1 1 calc R U . . .
C12 C 0.0439(3) 0.8561(7) 0.4371(5) 0.0152(14) Uani 1 1 d . . . . .
C13 C -0.0181(4) 0.8149(7) 0.3834(6) 0.0174(16) Uani 1 1 d . . . . .
C14 C 0.1058(4) 0.7884(7) 0.4204(6) 0.0172(17) Uani 1 1 d . . . . .
H14 H 0.109175 0.718992 0.373273 0.021 Uiso 1 1 calc R U . . .
C15 C 0.5632(3) 0.5995(6) 0.2770(7) 0.0185(13) Uani 1 1 d . . . . .
H15A H 0.542682 0.505025 0.274764 0.022 Uiso 1 1 calc R U . . .
H15B H 0.593538 0.606914 0.223425 0.022 Uiso 1 1 calc R U . . .
C16 C 0.6036(3) 0.6109(7) 0.3662(6) 0.0175(15) Uani 1 1 d . . . . .
C17 C 0.6702(3) 0.6591(7) 0.3617(6) 0.0168(15) Uani 1 1 d . . . . .
H17 H 0.687669 0.692544 0.304705 0.020 Uiso 1 1 calc R U . . .
C18 C 0.7105(3) 0.6572(7) 0.4425(6) 0.0164(14) Uani 1 1 d . . . . .
C19 C 0.7860(3) 0.6864(7) 0.4315(6) 0.0163(15) Uani 1 1 d . . . . .
C20 C 0.6843(3) 0.6128(7) 0.5291(6) 0.0168(15) Uani 1 1 d . . . . .
H20 H 0.710462 0.616942 0.583699 0.020 Uiso 1 1 calc R U . . .
C21 C 0.6181(3) 0.5618(7) 0.5330(6) 0.0159(14) Uani 1 1 d . . . . .
C22 C 0.5900(3) 0.4972(7) 0.6219(6) 0.0161(14) Uani 1 1 d . . . . .
C23 C 0.5797(3) 0.5592(7) 0.4516(6) 0.0186(15) Uani 1 1 d . . . . .
H23 H 0.536452 0.521477 0.454204 0.022 Uiso 1 1 calc R U . . .
O9 O 0.7834(3) 0.8628(7) 0.6667(5) 0.0290(14) Uani 1 1 d . . . . .
H9A H 0.7404(6) 0.853(11) 0.676(8) 0.043 Uiso 1 1 d . U . . .
H9B H 0.799(6) 0.814(12) 0.630(10) 0.043 Uiso 1 1 d . U . . .
O10 O 0.9171(3) 0.5164(6) 0.5381(5) 0.0312(13) Uani 1 1 d G . . . .
H10A H 0.951786 0.548742 0.566073 0.047 Uiso 1 1 d G U . . .
H10B H 0.891164 0.585614 0.523818 0.047 Uiso 1 1 d DG U . . .
O11 O 0.9017(4) 0.2639(10) 0.6367(10) 0.071(3) Uani 1 1 d G . . . .
H11A H 0.939791 0.222540 0.639224 0.106 Uiso 1 1 d G U . . .
H11B H 0.910192 0.346803 0.614588 0.106 Uiso 1 1 d G U . . .
O12 O 0.7894(3) 0.1500(7) 0.7145(5) 0.0419(17) Uani 1 1 d DG . . . .
H12A H 0.791946 0.059128 0.710850 0.063 Uiso 1 1 d G U . . .
H12B H 0.815123 0.187601 0.673304 0.063 Uiso 1 1 d G U . . .
O13 O 0.7575(7) 0.4226(16) 0.7506(14) 0.069(6) Uani 0.5 1 d G . P . .
H13A H 0.765022 0.335958 0.734908 0.103 Uiso 0.5 1 d DG U P . .
H13B H 0.719257 0.448237 0.729602 0.103 Uiso 0.5 1 d DG U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.019(5) 1_655 ?
Zn1 O2 2.375(5) 1_655 ?
Zn1 O4 2.022(5) 2_674 ?
Zn1 O6 2.034(5) 4_654 ?
Zn1 O7 1.979(5) . ?
O1 C13 1.277(9) . ?
O2 C13 1.232(9) . ?
O3 C10 1.253(9) . ?
O4 C10 1.267(10) . ?
O5 C22 1.254(9) . ?
O6 C22 1.271(10) . ?
O7 C19 1.243(10) . ?
O8 C19 1.241(10) . ?
N1 H1 0.9800 . ?
N1 C4 1.505(9) . ?
N1 C5 1.492(9) . ?
N1 C6 1.510(10) . ?
N2 H2 0.9800 . ?
N2 C1 1.488(9) . ?
N2 C2 1.497(10) . ?
N2 C15 1.518(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.534(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.513(11) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.518(9) . ?
C7 C8 1.381(11) . ?
C7 C14 1.384(11) . ?
C8 H8 0.9300 . ?
C8 C9 1.404(10) . ?
C9 C10 1.498(11) . ?
C9 C11 1.395(10) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(11) . ?
C12 C13 1.498(10) . ?
C12 C14 1.401(10) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.498(12) . ?
C16 C17 1.400(9) . ?
C16 C23 1.381(11) . ?
C17 H17 0.9300 . ?
C17 C18 1.393(11) . ?
C18 C19 1.533(9) . ?
C18 C20 1.391(11) . ?
C20 H20 0.9300 . ?
C20 C21 1.401(9) . ?
C21 C22 1.499(11) . ?
C21 C23 1.379(11) . ?
C23 H23 0.9300 . ?
O9 H9A 0.87(2) . ?
O9 H9B 0.75(13) . ?
O10 H10A 0.8499 . ?
O10 H10B 0.8495 . ?
O11 H11A 0.8508 . ?
O11 H11B 0.8500 . ?
O12 H12A 0.8499 . ?
O12 H12B 0.8492 . ?
O13 H13A 0.8503 . ?
O13 H13B 0.8503 . ?

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 Zn1 O2 59.31(19) 1_655 1_655 ?
O1 Zn1 O4 131.7(2) 1_655 2_674 ?
O1 Zn1 O6 101.8(2) 1_655 4_654 ?
O4 Zn1 O2 89.19(19) 2_674 1_655 ?
O4 Zn1 O6 102.4(2) 2_674 4_654 ?
O6 Zn1 O2 160.65(19) 4_654 1_655 ?
O7 Zn1 O1 119.2(2) . 1_655 ?
O7 Zn1 O2 99.9(2) . 1_655 ?
O7 Zn1 O4 100.3(2) . 2_674 ?
O7 Zn1 O6 93.3(2) . 4_654 ?
C13 O1 Zn1 96.7(4) . 1_455 ?
C13 O2 Zn1 81.7(4) . 1_455 ?
C10 O4 Zn1 103.5(4) . 2_675 ?
C22 O6 Zn1 131.3(4) . 4_655 ?
C19 O7 Zn1 136.2(5) . . ?
C4 N1 H1 108.6 . . ?
C4 N1 C6 107.0(6) . . ?
C5 N1 H1 108.6 . . ?
C5 N1 C4 111.0(6) . . ?
C5 N1 C6 112.8(6) . . ?
C6 N1 H1 108.6 . . ?
C1 N2 H2 106.4 . . ?
C1 N2 C2 113.4(6) . . ?
C1 N2 C15 110.8(5) . . ?
C2 N2 H2 106.4 . . ?
C2 N2 C15 112.8(6) . . ?
C15 N2 H2 106.4 . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C2 H2A 109.1 . . ?
N2 C2 H2B 109.1 . . ?
N2 C2 C3 112.5(6) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
C4 C3 C2 105.9(6) . . ?
C4 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
N1 C4 C3 115.2(6) . . ?
N1 C4 H4A 108.5 . . ?
N1 C4 H4B 108.5 . . ?
C3 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 108.6 . . ?
N1 C6 H6B 108.6 . . ?
N1 C6 C7 114.5(6) . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C8 C7 C6 119.5(6) . . ?
C8 C7 C14 120.0(6) . . ?
C14 C7 C6 120.3(6) . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.7(7) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C10 120.7(7) . . ?
C11 C9 C8 118.2(7) . . ?
C11 C9 C10 121.1(7) . . ?
O3 C10 O4 122.6(7) . . ?
O3 C10 C9 119.0(7) . . ?
O4 C10 C9 118.4(6) . . ?
C9 C11 H11 119.2 . . ?
C12 C11 C9 121.6(6) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C13 119.5(6) . . ?
C11 C12 C14 119.1(7) . . ?
C14 C12 C13 121.4(6) . . ?
O1 C13 Zn1 53.0(4) . 1_455 ?
O1 C13 C12 117.8(6) . . ?
O2 C13 Zn1 69.3(4) . 1_455 ?
O2 C13 O1 122.2(7) . . ?
O2 C13 C12 120.0(6) . . ?
C12 C13 Zn1 169.9(5) . 1_455 ?
C7 C14 C12 120.3(7) . . ?
C7 C14 H14 119.9 . . ?
C12 C14 H14 119.9 . . ?
N2 C15 H15A 108.5 . . ?
N2 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 N2 115.2(6) . . ?
C16 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
C17 C16 C15 119.5(7) . . ?
C23 C16 C15 121.6(6) . . ?
C23 C16 C17 118.4(7) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.1(7) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C19 118.5(7) . . ?
C20 C18 C17 120.5(6) . . ?
C20 C18 C19 120.6(7) . . ?
O7 C19 C18 113.4(7) . . ?
O8 C19 O7 127.8(7) . . ?
O8 C19 C18 118.8(7) . . ?
C18 C20 H20 120.4 . . ?
C18 C20 C21 119.2(7) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 C22 121.3(7) . . ?
C23 C21 C20 119.5(7) . . ?
C23 C21 C22 119.0(6) . . ?
O5 C22 O6 123.1(7) . . ?
O5 C22 C21 116.5(7) . . ?
O6 C22 C21 120.3(6) . . ?
C16 C23 H23 119.0 . . ?
C21 C23 C16 122.1(7) . . ?
C21 C23 H23 119.0 . . ?
H9A O9 H9B 116(10) . . ?
H10A O10 H10B 109.5 . . ?
H11A O11 H11B 104.5 . . ?
H12A O12 H12B 109.5 . . ?
H13A O13 H13B 109.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O12 0.98 1.82 2.759(10) 159.9 2_664 yes
N2 H2 O5 0.98 1.70 2.647(9) 160.5 2_664 yes
O9 H9A O4 0.87(2) 1.9630(14) 2.822(7) 170(10) 3_575 yes
O9 H9B O8 0.75(13) 2.06(14) 2.778(9) 162(13) . yes
O10 H10A O5 0.85 1.99 2.821(8) 166.8 3_565 yes
O10 H10B O8 0.85 1.89 2.731(7) 168.3 . yes
O11 H11A O3 0.85 1.96 2.796(9) 166.4 1_645 yes
O11 H11B O10 0.85 1.92 2.751(11) 165.8 . yes
O12 H12A O9 0.85 1.94 2.763(9) 162.5 1_545 yes
O12 H12B O11 0.85 1.93 2.703(11) 150.5 . yes
O13 H13A O12 0.85 1.82 2.667(16) 172.2 . yes

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
Zn1 O1 C13 O2 4.4(8) 1_455 . . . ?
Zn1 O1 C13 C12 -175.3(6) 1_455 . . . ?
Zn1 O2 C13 O1 -3.8(7) 1_455 . . . ?
Zn1 O2 C13 C12 175.9(7) 1_455 . . . ?
Zn1 O4 C10 O3 1.8(8) 2_675 . . . ?
Zn1 O4 C10 C9 -177.6(5) 2_675 . . . ?
Zn1 O6 C22 O5 -111.5(7) 4_655 . . . ?
Zn1 O6 C22 C21 71.8(8) 4_655 . . . ?
Zn1 O7 C19 O8 -11.0(12) . . . . ?
Zn1 O7 C19 C18 171.1(5) . . . . ?
N1 C6 C7 C8 -92.1(9) . . . . ?
N1 C6 C7 C14 91.4(8) . . . . ?
N2 C2 C3 C4 168.4(6) . . . . ?
N2 C15 C16 C17 -108.2(7) . . . . ?
N2 C15 C16 C23 79.6(8) . . . . ?
C1 N2 C2 C3 72.3(8) . . . . ?
C1 N2 C15 C16 67.2(9) . . . . ?
C2 N2 C15 C16 -61.1(7) . . . . ?
C2 C3 C4 N1 169.8(7) . . . . ?
C4 N1 C6 C7 173.4(7) . . . . ?
C5 N1 C4 C3 -63.0(10) . . . . ?
C5 N1 C6 C7 51.1(9) . . . . ?
C6 N1 C4 C3 173.6(7) . . . . ?
C6 C7 C8 C9 -178.6(7) . . . . ?
C6 C7 C14 C12 177.3(7) . . . . ?
C7 C8 C9 C10 -178.7(7) . . . . ?
C7 C8 C9 C11 1.1(11) . . . . ?
C8 C7 C14 C12 0.8(11) . . . . ?
C8 C9 C10 O3 178.6(7) . . . . ?
C8 C9 C10 O4 -2.0(11) . . . . ?
C8 C9 C11 C12 1.1(11) . . . . ?
C9 C11 C12 C13 176.4(7) . . . . ?
C9 C11 C12 C14 -2.4(11) . . . . ?
C10 C9 C11 C12 -179.1(7) . . . . ?
C11 C9 C10 O3 -1.2(11) . . . . ?
C11 C9 C10 O4 178.2(7) . . . . ?
C11 C12 C13 Zn1 -178(3) . . . 1_455 ?
C11 C12 C13 O1 -155.7(7) . . . . ?
C11 C12 C13 O2 24.6(11) . . . . ?
C11 C12 C14 C7 1.4(11) . . . . ?
C13 C12 C14 C7 -177.4(7) . . . . ?
C14 C7 C8 C9 -2.1(11) . . . . ?
C14 C12 C13 Zn1 1(4) . . . 1_455 ?
C14 C12 C13 O1 23.0(11) . . . . ?
C14 C12 C13 O2 -156.7(8) . . . . ?
C15 N2 C2 C3 -160.7(6) . . . . ?
C15 C16 C17 C18 -173.8(6) . . . . ?
C15 C16 C23 C21 176.2(6) . . . . ?
C16 C17 C18 C19 169.8(6) . . . . ?
C16 C17 C18 C20 -2.5(10) . . . . ?
C17 C16 C23 C21 3.9(10) . . . . ?
C17 C18 C19 O7 -17.4(9) . . . . ?
C17 C18 C19 O8 164.4(6) . . . . ?
C17 C18 C20 C21 3.8(10) . . . . ?
C18 C20 C21 C22 173.0(6) . . . . ?
C18 C20 C21 C23 -1.3(10) . . . . ?
C19 C18 C20 C21 -168.3(6) . . . . ?
C20 C18 C19 O7 154.9(7) . . . . ?
C20 C18 C19 O8 -23.3(9) . . . . ?
C20 C21 C22 O5 -152.4(6) . . . . ?
C20 C21 C22 O6 24.5(10) . . . . ?
C20 C21 C23 C16 -2.6(10) . . . . ?
C22 C21 C23 C16 -177.1(6) . . . . ?
C23 C16 C17 C18 -1.3(10) . . . . ?
C23 C21 C22 O5 22.0(9) . . . . ?
C23 C21 C22 O6 -161.2(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.652
_oxdiff_exptl_absorpt_empirical_full_min 0.184


#=END OF CIF
####################################################################### 
# 
# 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_1Cd
_database_code_depnum_ccdc_archive 'CCDC 1968826'
loop_
_audit_author_name
_audit_author_address
'Stuart Batten'
;Monash University
Australia
;
_audit_update_record             
;
2020-03-14 deposited with the CCDC.	2020-03-23 downloaded from the CCDC.
;

_audit_creation_date             2020-03-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 Cd N2 O8, 2(H2 O), O'
_chemical_formula_sum            'C23 H33 Cd N2 O12.50'
_chemical_formula_weight         649.91
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0035 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8048 1.2290 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0065 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0116 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   20.4570(3)
_cell_length_b                   9.3200(2)
_cell_length_c                   14.1950(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2706.41(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7394
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      31.817
_cell_measurement_theta_min      2.186
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.780
_exptl_absorpt_coefficient_mu    0.874
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1332
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   0.7463
_exptl_transmission_factor_min   0.7159
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.807
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            47704
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         31.817
_diffrn_reflns_theta_min         2.186
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.807
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Omega Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.7109
_diffrn_source                   "'MX1 Beamline Australian Synchrotron"
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.791
_reflns_number_gt                7280
_reflns_number_total             7394
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'AS QEGUI'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.582
_refine_diff_density_min         -1.178
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details 
;
 Flack x determined using 3396 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.039(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         7394
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+4.0679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0896
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N1A-C5A
 1.5 with sigma of 0.02
 O10-H10B = O10-H10A
 0.84 with sigma of 0.02
 H10B-O5
 1.969 with sigma of 0.001
 H10B-H10A
 1.377 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C4A) \\sim Ueq, Uanis(C4B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N1B) \\sim Ueq, Uanis(N1A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: N1A(0.33333) H1A(0.33333) O11B(0.66667) C4A(0.33333) H4AA(0.33333)
 H4AB(0.33333) C4B(0.66667) H4BA(0.66667) H4BB(0.66667) C5B(0.66667)
 H5BA(0.66667) H5BB(0.66667) H5BC(0.66667) C5A(0.33333) H5AA(0.33333)
 H5AB(0.33333) H5AC(0.33333) N1B(0.66667) H1BA(0.66667) O11A(0.33333)
5.a Free rotating group:
 O9(H9A,H9B)
5.b Ternary CH refined with riding coordinates:
 N1A(H1A), N2(H2), N1B(H1BA)
5.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C15(H15A,H15B), C4A(H4AA,H4AB),
 C4B(H4BA,H4BB)
5.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C14(H14), C17(H17), C20(H20), C23(H23)
5.e Idealised Me refined as rotating group:
 C1(H1B,H1C,H1D), C5B(H5BA,H5BB,H5BC), C5A(H5AA,H5AB,H5AC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.10775(2) 0.28094(2) 0.29902(3) 0.01630(8) Uani 1 1 d . . . . .
O1 O 1.00534(16) 0.3105(3) 0.3561(2) 0.0241(6) Uani 1 1 d . . . . .
O2 O 1.05519(15) 0.1138(3) 0.4048(2) 0.0208(6) Uani 1 1 d . . . . .
O3 O 0.94664(15) -0.1608(4) 0.6675(2) 0.0222(6) Uani 1 1 d . . . . .
O4 O 0.84317(15) -0.1159(3) 0.7006(2) 0.0222(6) Uani 1 1 d . . . . .
O5 O 0.45799(14) 0.5973(4) 0.6273(2) 0.0242(6) Uani 1 1 d D . . . .
O6 O 0.38324(17) 0.4851(3) 0.7148(2) 0.0244(6) Uani 1 1 d . . . . .
O7 O 0.20021(17) 0.3255(5) 0.3655(3) 0.0391(9) Uani 1 1 d . . . . .
O8 O 0.18616(18) 0.3070(8) 0.5181(3) 0.0642(18) Uani 1 1 d . . . . .
N1A N 0.7152(15) 0.183(3) 0.4103(16) 0.017(5) Uani 0.3333 1 d D U P A 1
H1A H 0.699573 0.099798 0.448495 0.021 Uiso 0.3333 1 calc R U P A 1
N2 N 0.49030(15) 0.2847(3) 0.2819(2) 0.0138(7) Uani 1 1 d . . . . .
H2 H 0.513431 0.308096 0.221736 0.017 Uiso 1 1 calc R U . . .
C1 C 0.46270(19) 0.1388(4) 0.2699(3) 0.0216(8) Uani 1 1 d . . . . .
H1B H 0.498355 0.069681 0.261782 0.032 Uiso 1 1 calc R U . . .
H1C H 0.434446 0.137029 0.214117 0.032 Uiso 1 1 calc R U . . .
H1D H 0.437064 0.113321 0.325713 0.032 Uiso 1 1 calc R U . . .
C2 C 0.5406(2) 0.2931(4) 0.3583(3) 0.0204(8) Uani 1 1 d . . . . .
H2A H 0.522247 0.251882 0.416904 0.024 Uiso 1 1 calc R U . . .
H2B H 0.551140 0.395062 0.370651 0.024 Uiso 1 1 calc R U . . .
C3 C 0.60332(19) 0.2131(4) 0.3330(4) 0.0239(9) Uani 1 1 d . . . . .
H3A H 0.599542 0.110457 0.350008 0.029 Uiso 1 1 calc R U . B 1
H3B H 0.611978 0.220324 0.264517 0.029 Uiso 1 1 calc R U . B 1
C6 C 0.7660(2) 0.2625(5) 0.4642(4) 0.0279(9) Uani 1 1 d . . . . .
H6A H 0.747294 0.289826 0.525941 0.033 Uiso 1 1 calc R U . A 1
H6B H 0.776095 0.352294 0.429870 0.033 Uiso 1 1 calc R U . A 1
C7 C 0.82912(19) 0.1836(4) 0.4813(3) 0.0183(7) Uani 1 1 d . . . . .
C8 C 0.83249(18) 0.0827(4) 0.5533(3) 0.0171(7) Uani 1 1 d . . . . .
H8 H 0.794524 0.061590 0.589234 0.021 Uiso 1 1 calc R U . . .
C9 C 0.89074(17) 0.0123(4) 0.5732(3) 0.0165(7) Uani 1 1 d . . . . .
C10 C 0.89411(17) -0.0948(4) 0.6516(3) 0.0165(7) Uani 1 1 d . . . . .
C11 C 0.94683(17) 0.0460(4) 0.5212(3) 0.0153(6) Uani 1 1 d . . . . .
H11 H 0.986774 -0.002416 0.533764 0.018 Uiso 1 1 calc R U . . .
C12 C 0.94409(18) 0.1503(4) 0.4513(3) 0.0160(6) Uani 1 1 d . . . . .
C13 C 1.00565(19) 0.1934(4) 0.4009(3) 0.0169(6) Uani 1 1 d . . . . .
C14 C 0.8851(2) 0.2178(4) 0.4313(3) 0.0187(7) Uani 1 1 d . . . . .
H14 H 0.883157 0.288132 0.382929 0.022 Uiso 1 1 calc R U . . .
C15 C 0.43726(15) 0.3962(3) 0.2933(3) 0.0154(6) Uani 1 1 d . . . . .
H15A H 0.406761 0.387616 0.239466 0.018 Uiso 1 1 calc R U . . .
H15B H 0.457661 0.492330 0.289780 0.018 Uiso 1 1 calc R U . . .
C16 C 0.39801(16) 0.3876(4) 0.3834(3) 0.0141(6) Uani 1 1 d . . . . .
C17 C 0.33311(17) 0.3428(4) 0.3788(3) 0.0148(6) Uani 1 1 d . . . . .
H17 H 0.315727 0.307874 0.321137 0.018 Uiso 1 1 calc R U . . .
C18 C 0.29343(17) 0.3494(4) 0.4593(3) 0.0156(6) Uani 1 1 d . . . . .
C19 C 0.22110(18) 0.3227(5) 0.4479(3) 0.0196(7) Uani 1 1 d . . . . .
C20 C 0.31914(17) 0.3961(4) 0.5444(3) 0.0160(6) Uani 1 1 d . . . . .
H20 H 0.293093 0.394965 0.599826 0.019 Uiso 1 1 calc R U . . .
C21 C 0.38368(18) 0.4447(4) 0.5478(3) 0.0150(6) Uani 1 1 d . . . . .
C22 C 0.41101(19) 0.5124(4) 0.6365(3) 0.0165(6) Uani 1 1 d . . . . .
C23 C 0.42226(17) 0.4425(4) 0.4676(3) 0.0149(6) Uani 1 1 d . . . . .
H23 H 0.465620 0.478805 0.470070 0.018 Uiso 1 1 calc R U . . .
O9 O 0.70648(17) -0.1481(5) 0.6773(3) 0.0417(10) Uani 1 1 d G . . . .
H9A H 0.701453 -0.213182 0.633857 0.063 Uiso 1 1 d G U . . .
H9B H 0.748435 -0.133495 0.679633 0.063 Uiso 1 1 d G U . . .
O10 O 0.5789(3) 0.5290(8) 0.5401(5) 0.0758(19) Uani 1 1 d D . . . .
H10A H 0.611(3) 0.578(9) 0.522(10) 0.114 Uiso 1 1 d D U . . .
H10B H 0.5433(17) 0.572(8) 0.565(5) 0.114 Uiso 1 1 d D U . . .
O11B O 0.7452(6) 0.3707(12) 0.2488(9) 0.089(3) Uiso 0.6667 1 d . . P C 2
C4A C 0.6567(18) 0.282(3) 0.387(2) 0.027(6) Uani 0.3333 1 d . U P A 1
H4AA H 0.638422 0.318764 0.447022 0.032 Uiso 0.3333 1 calc R U P A 1
H4AB H 0.673001 0.365222 0.350891 0.032 Uiso 0.3333 1 calc R U P A 1
C4B C 0.6542(7) 0.2565(14) 0.4086(11) 0.026(3) Uani 0.6667 1 d . U P A 2
H4BA H 0.658084 0.362385 0.409644 0.031 Uiso 0.6667 1 calc R U P A 2
H4BB H 0.638228 0.225449 0.471226 0.031 Uiso 0.6667 1 calc R U P A 2
C5B C 0.7184(4) 0.0324(7) 0.3969(6) 0.0326(17) Uani 0.6667 1 d . . P A 2
H5BA H 0.762887 -0.005765 0.391330 0.049 Uiso 0.6667 1 calc R U P A 2
H5BB H 0.691435 -0.004862 0.345436 0.049 Uiso 0.6667 1 calc R U P A 2
H5BC H 0.699642 0.002943 0.457436 0.049 Uiso 0.6667 1 calc R U P A 2
C5A C 0.7431(8) 0.129(2) 0.3175(13) 0.050(6) Uani 0.3333 1 d D . P A 1
H5AA H 0.781633 0.069258 0.329979 0.075 Uiso 0.3333 1 calc R U P A 1
H5AB H 0.755755 0.210745 0.278118 0.075 Uiso 0.3333 1 calc R U P A 1
H5AC H 0.710042 0.071749 0.284563 0.075 Uiso 0.3333 1 calc R U P A 1
N1B N 0.7204(8) 0.1927(16) 0.3918(9) 0.018(2) Uani 0.6667 1 d . U P A 2
H1BA H 0.735318 0.221028 0.327354 0.022 Uiso 0.6667 1 calc R U P A 2
O11A O 0.6438(6) 0.0120(13) 0.5320(10) 0.040(3) Uiso 0.3333 1 d . . P D 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 O1 2.263(3) 1_455 ?
Cd1 O2 2.416(3) 1_455 ?
Cd1 O3 2.445(3) 2_654 ?
Cd1 O4 2.308(3) 2_654 ?
Cd1 O6 2.255(3) 3_554 ?
Cd1 O7 2.154(3) . ?
O1 C13 1.264(5) . ?
O2 C13 1.257(5) . ?
O3 C10 1.259(5) . ?
O4 C10 1.269(5) . ?
O5 C22 1.252(5) . ?
O6 C22 1.274(5) . ?
O7 C19 1.245(6) . ?
O8 C19 1.236(6) . ?
N1A H1A 1.0000 . ?
N1A C6 1.49(3) . ?
N1A C4A 1.54(5) . ?
N1A C5A 1.52(2) . ?
N2 H2 1.0000 . ?
N2 C1 1.482(5) . ?
N2 C2 1.498(5) . ?
N2 C15 1.511(4) . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.527(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4A 1.48(4) . ?
C3 C4B 1.549(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.506(6) . ?
C6 N1B 1.532(16) . ?
C7 C8 1.390(6) . ?
C7 C14 1.385(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(5) . ?
C9 C10 1.496(6) . ?
C9 C11 1.400(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(5) . ?
C12 C13 1.503(5) . ?
C12 C14 1.391(5) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.512(6) . ?
C16 C17 1.393(4) . ?
C16 C23 1.391(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.403(5) . ?
C18 C19 1.509(5) . ?
C18 C20 1.388(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.397(5) . ?
C21 C22 1.515(5) . ?
C21 C23 1.386(5) . ?
C23 H23 0.9500 . ?
O9 H9A 0.8707 . ?
O9 H9B 0.8696 . ?
O10 H10A 0.84(3) . ?
O10 H10B 0.90(2) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B N1B 1.50(2) . ?
C5B H5BA 0.9800 . ?
C5B H5BB 0.9800 . ?
C5B H5BC 0.9800 . ?
C5B N1B 1.496(16) . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
N1B H1BA 1.0000 . ?

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 Cd1 O2 56.23(10) 1_455 1_455 ?
O1 Cd1 O3 84.70(12) 1_455 2_654 ?
O1 Cd1 O4 134.47(11) 1_455 2_654 ?
O2 Cd1 O3 88.66(12) 1_455 2_654 ?
O4 Cd1 O2 98.05(11) 2_654 1_455 ?
O4 Cd1 O3 55.28(11) 2_654 2_654 ?
O6 Cd1 O1 99.36(12) 3_554 1_455 ?
O6 Cd1 O2 155.52(11) 3_554 1_455 ?
O6 Cd1 O3 91.08(11) 3_554 2_654 ?
O6 Cd1 O4 101.88(12) 3_554 2_654 ?
O7 Cd1 O1 129.25(15) . 1_455 ?
O7 Cd1 O2 104.06(14) . 1_455 ?
O7 Cd1 O3 145.33(14) . 2_654 ?
O7 Cd1 O4 90.67(14) . 2_654 ?
O7 Cd1 O6 89.88(15) . 3_554 ?
C13 O1 Cd1 94.0(2) . 1_655 ?
C13 O2 Cd1 87.2(2) . 1_655 ?
C10 O3 Cd1 88.4(2) . 2_655 ?
C10 O4 Cd1 94.5(2) . 2_655 ?
C22 O6 Cd1 126.5(3) . 3 ?
C19 O7 Cd1 135.1(3) . . ?
C6 N1A H1A 109.3 . . ?
C6 N1A C4A 111(2) . . ?
C6 N1A C5A 110.3(19) . . ?
C4A N1A H1A 109.3 . . ?
C5A N1A H1A 109.3 . . ?
C5A N1A C4A 108(2) . . ?
C1 N2 H2 106.4 . . ?
C1 N2 C2 113.1(3) . . ?
C1 N2 C15 111.7(3) . . ?
C2 N2 H2 106.4 . . ?
C2 N2 C15 112.3(3) . . ?
C15 N2 H2 106.4 . . ?
N2 C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
N2 C1 H1D 109.5 . . ?
H1B C1 H1C 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
N2 C2 H2A 109.1 . . ?
N2 C2 H2B 109.1 . . ?
N2 C2 C3 112.4(4) . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C2 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
C2 C3 C4B 105.9(7) . . ?
H3A C3 H3B 108.6 . . ?
C4A C3 C2 106.6(15) . . ?
C4A C3 H3A 110.4 . . ?
C4A C3 H3B 110.4 . . ?
N1A C6 H6A 108.3 . . ?
N1A C6 H6B 108.3 . . ?
N1A C6 C7 116.1(12) . . ?
H6A C6 H6B 107.4 . . ?
C7 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
C7 C6 N1B 115.0(7) . . ?
C8 C7 C6 119.5(4) . . ?
C14 C7 C6 120.9(4) . . ?
C14 C7 C8 119.5(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.8(4) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 C11 119.3(4) . . ?
C11 C9 C10 120.2(3) . . ?
O3 C10 Cd1 64.0(2) . 2_655 ?
O3 C10 O4 121.8(4) . . ?
O3 C10 C9 119.9(3) . . ?
O4 C10 Cd1 57.8(2) . 2_655 ?
O4 C10 C9 118.3(3) . . ?
C9 C10 Cd1 175.9(3) . 2_655 ?
C9 C11 H11 120.0 . . ?
C12 C11 C9 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 119.5(3) . . ?
C14 C12 C11 119.8(4) . . ?
C14 C12 C13 120.6(4) . . ?
O1 C13 Cd1 57.8(2) . 1_655 ?
O1 C13 C12 117.8(3) . . ?
O2 C13 Cd1 64.7(2) . 1_655 ?
O2 C13 O1 122.4(4) . . ?
O2 C13 C12 119.8(3) . . ?
C12 C13 Cd1 174.6(3) . 1_655 ?
C7 C14 C12 120.6(4) . . ?
C7 C14 H14 119.7 . . ?
C12 C14 H14 119.7 . . ?
N2 C15 H15A 108.3 . . ?
N2 C15 H15B 108.3 . . ?
N2 C15 C16 115.9(3) . . ?
H15A C15 H15B 107.4 . . ?
C16 C15 H15A 108.3 . . ?
C16 C15 H15B 108.3 . . ?
C17 C16 C15 118.8(3) . . ?
C23 C16 C15 121.2(3) . . ?
C23 C16 C17 119.4(3) . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0(3) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 118.2(3) . . ?
C20 C18 C17 120.2(3) . . ?
C20 C18 C19 121.1(3) . . ?
O7 C19 C18 115.7(4) . . ?
O8 C19 O7 124.2(4) . . ?
O8 C19 C18 120.0(4) . . ?
C18 C20 H20 120.3 . . ?
C18 C20 C21 119.3(3) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 C22 120.9(3) . . ?
C23 C21 C20 120.3(3) . . ?
C23 C21 C22 118.6(3) . . ?
O5 C22 O6 124.0(4) . . ?
O5 C22 C21 117.4(3) . . ?
O6 C22 C21 118.5(4) . . ?
C16 C23 H23 119.7 . . ?
C21 C23 C16 120.5(3) . . ?
C21 C23 H23 119.7 . . ?
H9A O9 H9B 104.7 . . ?
H10A O10 H10B 121(7) . . ?
N1A C4A H4AA 108.5 . . ?
N1A C4A H4AB 108.5 . . ?
C3 C4A N1A 115(3) . . ?
C3 C4A H4AA 108.5 . . ?
C3 C4A H4AB 108.5 . . ?
H4AA C4A H4AB 107.5 . . ?
C3 C4B H4BA 108.9 . . ?
C3 C4B H4BB 108.9 . . ?
H4BA C4B H4BB 107.8 . . ?
N1B C4B C3 113.2(11) . . ?
N1B C4B H4BA 108.9 . . ?
N1B C4B H4BB 108.9 . . ?
H5BA C5B H5BB 109.5 . . ?
H5BA C5B H5BC 109.5 . . ?
H5BB C5B H5BC 109.5 . . ?
N1B C5B H5BA 109.5 . . ?
N1B C5B H5BB 109.5 . . ?
N1B C5B H5BC 109.5 . . ?
N1A C5A H5AA 109.5 . . ?
N1A C5A H5AB 109.5 . . ?
N1A C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C6 N1B H1BA 108.4 . . ?
C4B N1B C6 106.0(10) . . ?
C4B N1B H1BA 108.4 . . ?
C5B N1B C6 114.1(10) . . ?
C5B N1B C4B 111.3(11) . . ?
C5B N1B H1BA 108.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O11A 1.00 1.84 2.77(3) 153.4 . yes
N1B H1BA O11B 1.00 1.80 2.670(18) 143.8 . yes
N2 H2 O5 1.00 1.71 2.673(4) 160.8 2_664 yes
O9 H9A O8 0.87 1.89 2.733(7) 163.4 4 yes
O9 H9B O4 0.87 1.97 2.832(5) 172.3 . yes
O10 H10A O8 0.84(3) 1.87(5) 2.692(8) 165(14) 4_565 yes
O10 H10B O5 0.90(2) 1.9692(15) 2.839(6) 161(6) . yes

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 C13 O2 3.9(5) 1_655 . . . ?
Cd1 O1 C13 C12 -176.4(3) 1_655 . . . ?
Cd1 O2 C13 O1 -3.6(4) 1_655 . . . ?
Cd1 O2 C13 C12 176.6(3) 1_655 . . . ?
Cd1 O3 C10 O4 -1.1(4) 2_655 . . . ?
Cd1 O3 C10 C9 178.7(3) 2_655 . . . ?
Cd1 O4 C10 O3 1.1(4) 2_655 . . . ?
Cd1 O4 C10 C9 -178.6(3) 2_655 . . . ?
Cd1 O6 C22 O5 -106.8(4) 3 . . . ?
Cd1 O6 C22 C21 76.5(4) 3 . . . ?
Cd1 O7 C19 O8 -9.7(9) . . . . ?
Cd1 O7 C19 C18 174.0(4) . . . . ?
N1A C6 C7 C8 -79.7(11) . . . . ?
N1A C6 C7 C14 105.3(11) . . . . ?
N2 C2 C3 C4A 154.0(10) . . . . ?
N2 C2 C3 C4B 169.1(6) . . . . ?
N2 C15 C16 C17 -109.5(4) . . . . ?
N2 C15 C16 C23 79.8(4) . . . . ?
C1 N2 C2 C3 69.0(4) . . . . ?
C1 N2 C15 C16 67.9(4) . . . . ?
C2 N2 C15 C16 -60.4(4) . . . . ?
C2 C3 C4A N1A 152.6(18) . . . . ?
C2 C3 C4B N1B -177.2(9) . . . . ?
C3 C4B N1B C6 172.4(8) . . . . ?
C3 C4B N1B C5B -63.0(13) . . . . ?
C6 N1A C4A C3 179.7(16) . . . . ?
C6 C7 C8 C9 -177.4(4) . . . . ?
C6 C7 C14 C12 176.3(4) . . . . ?
C7 C6 N1B C4B 161.6(8) . . . . ?
C7 C6 N1B C5B 38.8(12) . . . . ?
C7 C8 C9 C10 179.2(4) . . . . ?
C7 C8 C9 C11 1.3(6) . . . . ?
C8 C7 C14 C12 1.2(6) . . . . ?
C8 C9 C10 O3 178.1(4) . . . . ?
C8 C9 C10 O4 -2.1(6) . . . . ?
C8 C9 C11 C12 0.8(5) . . . . ?
C9 C11 C12 C13 175.4(3) . . . . ?
C9 C11 C12 C14 -1.9(5) . . . . ?
C10 C9 C11 C12 -177.1(3) . . . . ?
C11 C9 C10 O3 -4.0(6) . . . . ?
C11 C9 C10 O4 175.8(4) . . . . ?
C11 C12 C13 O1 -162.5(4) . . . . ?
C11 C12 C13 O2 17.3(6) . . . . ?
C11 C12 C14 C7 0.8(6) . . . . ?
C13 C12 C14 C7 -176.4(4) . . . . ?
C14 C7 C8 C9 -2.3(6) . . . . ?
C14 C12 C13 O1 14.8(6) . . . . ?
C14 C12 C13 O2 -165.4(4) . . . . ?
C15 N2 C2 C3 -163.4(3) . . . . ?
C15 C16 C17 C18 -172.8(3) . . . . ?
C15 C16 C23 C21 174.7(3) . . . . ?
C16 C17 C18 C19 170.4(3) . . . . ?
C16 C17 C18 C20 -2.1(6) . . . . ?
C17 C16 C23 C21 4.0(5) . . . . ?
C17 C18 C19 O7 -14.0(6) . . . . ?
C17 C18 C19 O8 169.5(5) . . . . ?
C17 C18 C20 C21 3.9(6) . . . . ?
C18 C20 C21 C22 172.8(3) . . . . ?
C18 C20 C21 C23 -1.8(6) . . . . ?
C19 C18 C20 C21 -168.3(4) . . . . ?
C20 C18 C19 O7 158.3(4) . . . . ?
C20 C18 C19 O8 -18.1(7) . . . . ?
C20 C21 C22 O5 -155.1(4) . . . . ?
C20 C21 C22 O6 21.8(5) . . . . ?
C20 C21 C23 C16 -2.1(6) . . . . ?
C22 C21 C23 C16 -176.9(3) . . . . ?
C23 C16 C17 C18 -1.9(5) . . . . ?
C23 C21 C22 O5 19.7(5) . . . . ?
C23 C21 C22 O6 -163.5(4) . . . . ?
C4A N1A C6 C7 -173.1(14) . . . . ?
C5A N1A C6 C7 -54(2) . . . . ?
C5A N1A C4A C3 59(3) . . . . ?
N1B C6 C7 C8 -92.0(7) . . . . ?
N1B C6 C7 C14 93.0(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'



#=END OF CIF
####################################################################### 
# 
# 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_2Cd
_database_code_depnum_ccdc_archive 'CCDC 1968827'
loop_
_audit_author_name
_audit_author_address
'Stuart Batten'
;Monash University
Australia
;
_audit_update_record             
;
2020-03-14 deposited with the CCDC.	2020-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Cd C23 H26 N2 O9, 7(H2 O), C3 H7 N O'
_chemical_formula_sum            'C26 H47 Cd N3 O17'
_chemical_formula_weight         786.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.1599(2)
_cell_length_b                   10.2806(2)
_cell_length_c                   18.7575(5)
_cell_angle_alpha                82.5340(10)
_cell_angle_beta                 83.4680(10)
_cell_angle_gamma                84.8720(10)
_cell_volume                     1545.62(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6323
_cell_measurement_theta_min      1.101
_cell_measurement_theta_max      26.369
_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   0.7127
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.792
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7127
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21209
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.101
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6323
_reflns_number_gt                5867
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
# SQUEEZE RESULTS (Version = 160617)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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 -0.009 0.500 0.500 398 197 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
9H2O per formula unit
;
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_diff_density_max         1.852
_refine_diff_density_min         -0.816
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         6323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0396P)²+1.7230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0757
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O10(H10D,H10E)
2.b Rotating group:
 O9(H9A,H9B)
2.c Ternary CH refined with riding coordinates:
 N1(H1), N2(H2)
2.d Secondary CH2 refined with riding coordinates:
 C9(H9C,H9D), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B)
2.e Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C17(H17), C19(H19), C21(H21)
2.f Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd01 Cd 0.16396(2) -0.08506(2) 1.11067(2) 0.01207(6) Uani 1 1 d . . . . .
O1 O 0.1953(2) 0.09420(16) 1.03212(9) 0.0197(4) Uani 1 1 d . . . . .
O2 O 0.1525(2) 0.17820(17) 1.13636(9) 0.0242(4) Uani 1 1 d . . . . .
O3 O 0.1591(2) 0.67472(16) 1.12227(9) 0.0196(4) Uani 1 1 d . . . . .
O4 O 0.2553(2) 0.78591(16) 1.01976(9) 0.0187(4) Uani 1 1 d . . . . .
O5 O 0.5752(2) 1.09530(17) 0.83694(9) 0.0178(3) Uani 1 1 d . . . . .
O6 O 0.8130(2) 1.11703(17) 0.76891(9) 0.0171(3) Uani 1 1 d . . . . .
O8 O 0.6336(2) 1.16621(18) 0.44936(9) 0.0221(4) Uani 1 1 d . . . . .
O9 O -0.1118(2) -0.08359(17) 1.10532(9) 0.0203(4) Uani 1 1 d . . . . .
H9A H -0.155487 -0.105113 1.068753 0.031 Uiso 1 1 d R U . . .
H9B H -0.174297 -0.014915 1.117534 0.031 Uiso 1 1 d R U . . .
N1 N 0.3361(3) 0.49204(19) 0.78829(11) 0.0163(4) Uani 1 1 d . . . . .
H1 H 0.403004 0.485777 0.740611 0.020 Uiso 1 1 calc R U . . .
N2 N 0.1382(2) 0.91787(19) 0.65475(10) 0.0140(4) Uani 1 1 d . . . . .
H2 H 0.215162 0.884989 0.614479 0.017 Uiso 1 1 calc R U . . .
C1 C 0.1904(3) 0.1896(2) 1.06977(13) 0.0174(5) Uani 1 1 d . . . . .
C2 C 0.2371(3) 0.3189(2) 1.02920(13) 0.0148(5) Uani 1 1 d . . . . .
C3 C 0.2042(3) 0.4346(2) 1.06111(12) 0.0149(4) Uani 1 1 d . . . . .
H3 H 0.148766 0.432627 1.108561 0.018 Uiso 1 1 calc R U . . .
C4 C 0.2526(3) 0.5537(2) 1.02341(12) 0.0134(4) Uani 1 1 d . . . . .
C5 C 0.3344(3) 0.5556(2) 0.95427(12) 0.0136(4) Uani 1 1 d . . . . .
H5 H 0.370170 0.636137 0.929192 0.016 Uiso 1 1 calc R U . . .
C6 C 0.3647(3) 0.4410(2) 0.92127(12) 0.0144(4) Uani 1 1 d . . . . .
C7 C 0.3167(3) 0.3228(2) 0.95933(13) 0.0152(5) Uani 1 1 d . . . . .
H7 H 0.338370 0.243957 0.937398 0.018 Uiso 1 1 calc R U . . .
C8 C 0.2203(3) 0.6788(2) 1.05739(12) 0.0144(5) Uani 1 1 d . . . . .
C9 C 0.4498(3) 0.4438(2) 0.84585(12) 0.0154(5) Uani 1 1 d . . . . .
H9C H 0.497495 0.354073 0.838328 0.019 Uiso 1 1 calc R U . . .
H9D H 0.542216 0.501725 0.840513 0.019 Uiso 1 1 calc R U . . .
C10 C 0.1978(4) 0.4060(3) 0.79146(18) 0.0357(7) Uani 1 1 d . . . . .
H10A H 0.242213 0.313999 0.792864 0.053 Uiso 1 1 calc R U . . .
H10B H 0.138317 0.430396 0.748585 0.053 Uiso 1 1 calc R U . . .
H10C H 0.121860 0.416774 0.835020 0.053 Uiso 1 1 calc R U . . .
C11 C 0.2781(3) 0.6341(2) 0.79030(13) 0.0168(5) Uani 1 1 d . . . . .
H11A H 0.372848 0.683424 0.797085 0.020 Uiso 1 1 calc R U . . .
H11B H 0.194387 0.641928 0.832368 0.020 Uiso 1 1 calc R U . . .
C12 C 0.2036(3) 0.6958(2) 0.72207(13) 0.0190(5) Uani 1 1 d . . . . .
H12A H 0.094093 0.662614 0.720368 0.023 Uiso 1 1 calc R U . . .
H12B H 0.276589 0.673917 0.678711 0.023 Uiso 1 1 calc R U . . .
C13 C 0.1863(3) 0.8438(2) 0.72430(12) 0.0167(5) Uani 1 1 d . . . . .
H13A H 0.101474 0.864835 0.764100 0.020 Uiso 1 1 calc R U . . .
H13B H 0.292680 0.872868 0.734612 0.020 Uiso 1 1 calc R U . . .
C14 C -0.0332(3) 0.8936(3) 0.64273(14) 0.0206(5) Uani 1 1 d . . . . .
H14A H -0.110607 0.920762 0.682930 0.031 Uiso 1 1 calc R U . . .
H14B H -0.039531 0.799661 0.639969 0.031 Uiso 1 1 calc R U . . .
H14C H -0.062225 0.944371 0.597389 0.031 Uiso 1 1 calc R U . . .
C15 C 0.1538(3) 1.0643(2) 0.65171(12) 0.0163(5) Uani 1 1 d . . . . .
H15A H 0.105414 1.110574 0.608442 0.020 Uiso 1 1 calc R U . . .
H15B H 0.090144 1.096634 0.694893 0.020 Uiso 1 1 calc R U . . .
C16 C 0.3312(3) 1.0963(2) 0.64880(12) 0.0152(5) Uani 1 1 d . . . . .
C17 C 0.4056(3) 1.0994(2) 0.71180(12) 0.0139(4) Uani 1 1 d . . . . .
H17 H 0.341735 1.087014 0.757431 0.017 Uiso 1 1 calc R U . . .
C18 C 0.5724(3) 1.1203(2) 0.70855(12) 0.0147(5) Uani 1 1 d . . . . .
C19 C 0.6632(3) 1.1430(2) 0.64158(13) 0.0163(5) Uani 1 1 d . . . . .
H19 H 0.776516 1.159582 0.639095 0.020 Uiso 1 1 calc R U . . .
C20 C 0.5910(3) 1.1417(2) 0.57816(12) 0.0178(5) Uani 1 1 d . . . . .
C21 C 0.4254(3) 1.1188(2) 0.58183(12) 0.0164(5) Uani 1 1 d . . . . .
H21 H 0.375285 1.118353 0.538559 0.020 Uiso 1 1 calc R U . . .
C22 C 0.6578(3) 1.1107(2) 0.77588(12) 0.0139(4) Uani 1 1 d . . . . .
C23 C 0.6984(3) 1.1554(3) 0.50689(14) 0.0279(6) Uani 1 1 d . . . . .
O7 O 0.8500(3) 1.1425(3) 0.50952(12) 0.0622(9) Uani 1 1 d . . . A 1
O10 O -0.3566(2) 0.11082(18) 1.12157(9) 0.0226(4) Uani 1 1 d G . . . .
H10D H -0.436636 0.061622 1.127307 0.034 Uiso 1 1 d G U . . .
H10E H -0.352411 0.143376 1.077405 0.034 Uiso 1 1 d G 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
Cd01 O1 2.2193(17) . ?
Cd01 O3 2.4544(17) 1_545 ?
Cd01 O4 2.3118(16) 1_545 ?
Cd01 O5 2.4326(17) 2_667 ?
Cd01 O6 2.2667(16) 2_667 ?
Cd01 O9 2.2625(17) . ?
Cd01 C8 2.726(2) 1_545 ?
Cd01 C22 2.684(2) 2_667 ?
O1 C1 1.276(3) . ?
O2 C1 1.245(3) . ?
O3 C8 1.259(3) . ?
O4 C8 1.265(3) . ?
O5 C22 1.260(3) . ?
O6 C22 1.265(3) . ?
O8 C23 1.243(3) . ?
O9 H9A 0.8693 . ?
O9 H9B 0.8729 . ?
N1 H1 1.0000 . ?
N1 C9 1.510(3) . ?
N1 C10 1.486(3) . ?
N1 C11 1.498(3) . ?
N2 H2 1.0000 . ?
N2 C13 1.497(3) . ?
N2 C14 1.489(3) . ?
N2 C15 1.515(3) . ?
C1 C2 1.501(3) . ?
C2 C3 1.391(3) . ?
C2 C7 1.392(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(3) . ?
C4 C5 1.388(3) . ?
C4 C8 1.498(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(3) . ?
C6 C7 1.391(3) . ?
C6 C9 1.501(3) . ?
C7 H7 0.9500 . ?
C9 H9C 0.9900 . ?
C9 H9D 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.519(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.522(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.506(3) . ?
C16 C17 1.394(3) . ?
C16 C21 1.399(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(3) . ?
C18 C19 1.387(3) . ?
C18 C22 1.499(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(3) . ?
C20 C21 1.386(3) . ?
C20 C23 1.511(3) . ?
C21 H21 0.9500 . ?
C23 O7 1.238(3) . ?
O10 H10D 0.8501 . ?
O10 H10E 0.8503 . ?

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 Cd01 O3 144.01(6) . 1_545 ?
O1 Cd01 O4 89.76(6) . 1_545 ?
O1 Cd01 O5 98.76(6) . 2_667 ?
O1 Cd01 O6 129.86(6) . 2_667 ?
O1 Cd01 O9 94.84(6) . . ?
O1 Cd01 C8 116.98(7) . 1_545 ?
O1 Cd01 C22 116.29(7) . 2_667 ?
O3 Cd01 C8 27.49(6) 1_545 1_545 ?
O3 Cd01 C22 89.36(6) 1_545 2_667 ?
O4 Cd01 O3 55.04(6) 1_545 1_545 ?
O4 Cd01 O5 97.00(6) 1_545 2_667 ?
O4 Cd01 C8 27.55(6) 1_545 1_545 ?
O4 Cd01 C22 116.78(6) 1_545 2_667 ?
O5 Cd01 O3 93.36(6) 2_667 1_545 ?
O5 Cd01 C8 96.07(6) 2_667 1_545 ?
O5 Cd01 C22 27.96(6) 2_667 2_667 ?
O6 Cd01 O3 84.68(6) 2_667 1_545 ?
O6 Cd01 O4 131.63(6) 2_667 1_545 ?
O6 Cd01 O5 55.97(6) 2_667 2_667 ?
O6 Cd01 C8 108.88(6) 2_667 1_545 ?
O6 Cd01 C22 28.02(6) 2_667 2_667 ?
O9 Cd01 O3 84.79(6) . 1_545 ?
O9 Cd01 O4 98.97(6) . 1_545 ?
O9 Cd01 O5 159.02(6) . 2_667 ?
O9 Cd01 O6 103.07(6) . 2_667 ?
O9 Cd01 C8 91.87(7) . 1_545 ?
O9 Cd01 C22 131.06(7) . 2_667 ?
C22 Cd01 C8 104.52(7) 2_667 1_545 ?
C1 O1 Cd01 106.00(15) . . ?
C8 O3 Cd01 88.37(13) . 1_565 ?
C8 O4 Cd01 94.77(14) . 1_565 ?
C22 O5 Cd01 87.19(14) . 2_667 ?
C22 O6 Cd01 94.66(13) . 2_667 ?
Cd01 O9 H9A 123.7 . . ?
Cd01 O9 H9B 118.1 . . ?
H9A O9 H9B 104.0 . . ?
C9 N1 H1 106.7 . . ?
C10 N1 H1 106.7 . . ?
C10 N1 C9 111.66(19) . . ?
C10 N1 C11 112.9(2) . . ?
C11 N1 H1 106.7 . . ?
C11 N1 C9 111.56(18) . . ?
C13 N2 H2 107.9 . . ?
C13 N2 C15 111.97(18) . . ?
C14 N2 H2 107.9 . . ?
C14 N2 C13 111.15(18) . . ?
C14 N2 C15 109.92(18) . . ?
C15 N2 H2 107.9 . . ?
O1 C1 C2 116.0(2) . . ?
O2 C1 O1 123.2(2) . . ?
O2 C1 C2 120.8(2) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 C7 119.7(2) . . ?
C7 C2 C1 119.6(2) . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C8 120.7(2) . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 C8 119.6(2) . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 119.2(2) . . ?
C5 C6 C9 120.7(2) . . ?
C7 C6 C9 120.1(2) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.7(2) . . ?
C6 C7 H7 119.7 . . ?
O3 C8 Cd01 64.15(12) . 1_565 ?
O3 C8 O4 121.8(2) . . ?
O3 C8 C4 119.4(2) . . ?
O4 C8 Cd01 57.68(11) . 1_565 ?
O4 C8 C4 118.8(2) . . ?
C4 C8 Cd01 176.37(16) . 1_565 ?
N1 C9 H9C 108.9 . . ?
N1 C9 H9D 108.9 . . ?
C6 C9 N1 113.25(19) . . ?
C6 C9 H9C 108.9 . . ?
C6 C9 H9D 108.9 . . ?
H9C C9 H9D 107.7 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.0 . . ?
N1 C11 H11B 109.0 . . ?
N1 C11 C12 112.92(19) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C11 C12 H12A 110.3 . . ?
C11 C12 H12B 110.3 . . ?
C11 C12 C13 107.00(19) . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.3 . . ?
C13 C12 H12B 110.3 . . ?
N2 C13 C12 112.23(19) . . ?
N2 C13 H13A 109.2 . . ?
N2 C13 H13B 109.2 . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.2 . . ?
N2 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 N2 112.09(18) . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C17 C16 C15 121.2(2) . . ?
C17 C16 C21 119.1(2) . . ?
C21 C16 C15 119.6(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C22 121.2(2) . . ?
C19 C18 C17 119.2(2) . . ?
C19 C18 C22 119.5(2) . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.0(2) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C23 119.0(2) . . ?
C21 C20 C19 119.5(2) . . ?
C21 C20 C23 121.4(2) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.5(2) . . ?
C20 C21 H21 119.7 . . ?
O5 C22 Cd01 64.85(12) . 2_667 ?
O5 C22 O6 122.2(2) . . ?
O5 C22 C18 119.9(2) . . ?
O6 C22 Cd01 57.33(11) . 2_667 ?
O6 C22 C18 117.9(2) . . ?
C18 C22 Cd01 174.70(16) . 2_667 ?
O8 C23 C20 119.7(2) . . ?
O7 C23 O8 123.1(2) . . ?
O7 C23 C20 116.9(2) . . ?
H10D O10 H10E 104.5 . . ?

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
_geom_hbond_publ_flag
O9 H9A O1 0.87 1.94 2.758(2) 155.6 2_557 yes
O9 H9B O10 0.87 1.88 2.717(3) 159.3 . yes
N2 H2 O8 1.00 1.72 2.712(3) 173.0 2_676 yes
O10 H10D O5 0.85 2.05 2.865(2) 160.3 2_567 yes
O10 H10E O4 0.85 1.98 2.787(2) 158.8 2_567 yes

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
Cd01 O1 C1 O2 -8.6(3) . . . . ?
Cd01 O1 C1 C2 170.18(16) . . . . ?
Cd01 O3 C8 O4 0.9(2) 1_565 . . . ?
Cd01 O3 C8 C4 -178.98(19) 1_565 . . . ?
Cd01 O4 C8 O3 -0.9(2) 1_565 . . . ?
Cd01 O4 C8 C4 178.92(17) 1_565 . . . ?
Cd01 O5 C22 O6 -1.8(2) 2_667 . . . ?
Cd01 O5 C22 C18 177.36(19) 2_667 . . . ?
Cd01 O6 C22 O5 1.9(2) 2_667 . . . ?
Cd01 O6 C22 C18 -177.24(17) 2_667 . . . ?
O1 C1 C2 C3 166.7(2) . . . . ?
O1 C1 C2 C7 -14.3(3) . . . . ?
O2 C1 C2 C3 -14.5(4) . . . . ?
O2 C1 C2 C7 164.5(2) . . . . ?
N1 C11 C12 C13 -167.7(2) . . . . ?
N2 C15 C16 C17 -89.1(3) . . . . ?
N2 C15 C16 C21 88.6(3) . . . . ?
C1 C2 C3 C4 178.2(2) . . . . ?
C1 C2 C7 C6 -178.5(2) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C2 C3 C4 C8 -179.1(2) . . . . ?
C3 C2 C7 C6 0.5(3) . . . . ?
C3 C4 C5 C6 1.8(3) . . . . ?
C3 C4 C8 O3 4.8(3) . . . . ?
C3 C4 C8 O4 -175.0(2) . . . . ?
C4 C5 C6 C7 -2.1(3) . . . . ?
C4 C5 C6 C9 178.6(2) . . . . ?
C5 C4 C8 O3 -173.9(2) . . . . ?
C5 C4 C8 O4 6.3(3) . . . . ?
C5 C6 C7 C2 0.9(3) . . . . ?
C5 C6 C9 N1 -79.6(3) . . . . ?
C7 C2 C3 C4 -0.8(3) . . . . ?
C7 C6 C9 N1 101.1(2) . . . . ?
C8 C4 C5 C6 -179.5(2) . . . . ?
C9 N1 C11 C12 164.29(19) . . . . ?
C9 C6 C7 C2 -179.8(2) . . . . ?
C10 N1 C9 C6 -60.9(3) . . . . ?
C10 N1 C11 C12 -69.0(3) . . . . ?
C11 N1 C9 C6 66.5(2) . . . . ?
C11 C12 C13 N2 171.28(19) . . . . ?
C13 N2 C15 C16 67.2(2) . . . . ?
C14 N2 C13 C12 67.9(2) . . . . ?
C14 N2 C15 C16 -168.73(19) . . . . ?
C15 N2 C13 C12 -168.74(19) . . . . ?
C15 C16 C17 C18 175.7(2) . . . . ?
C15 C16 C21 C20 -176.7(2) . . . . ?
C16 C17 C18 C19 2.3(3) . . . . ?
C16 C17 C18 C22 -173.9(2) . . . . ?
C17 C16 C21 C20 1.1(3) . . . . ?
C17 C18 C19 C20 -1.6(4) . . . . ?
C17 C18 C22 O5 -6.5(3) . . . . ?
C17 C18 C22 O6 172.6(2) . . . . ?
C18 C19 C20 C21 0.7(4) . . . . ?
C18 C19 C20 C23 -174.9(2) . . . . ?
C19 C18 C22 O5 177.2(2) . . . . ?
C19 C18 C22 O6 -3.6(3) . . . . ?
C19 C20 C21 C16 -0.4(4) . . . . ?
C19 C20 C23 O8 -173.6(3) . . . . ?
C19 C20 C23 O7 13.2(4) . . . . ?
C21 C16 C17 C18 -2.0(3) . . . . ?
C21 C20 C23 O8 10.9(4) . . . . ?
C21 C20 C23 O7 -162.3(3) . . . . ?
C22 C18 C19 C20 174.7(2) . . . . ?
C23 C20 C21 C16 175.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'



#=END OF CIF
