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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2207267'
loop_
_audit_author_name
_audit_author_address
'Mark Elsegood'
;Loughborough University
United Kingdom
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT043_cr442               
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..      73.08 Check 
RESPONSE: Accounted for by Squeezed solvent
;
_vrf_PLAT602_cr442               
;
PROBLEM: Solvent Accessible VOID(S) in Structure ........          ! Check 
RESPONSE: Squeezed
;
_vrf_PLAT213_cr442               
;
PROBLEM: Atom C3              has ADP max/min Ratio .....        4.4 prolat
RESPONSE: Part of a disordered part of the structure; some restraints applied.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N2 O4 Zn, C3 H7 N O'
_chemical_formula_sum            'C16 H16 N3 O5 Zn'
_chemical_formula_weight         395.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   16.112(6)
_cell_length_b                   7.649(3)
_cell_length_c                   29.100(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.562(5)
_cell_angle_gamma                90
_cell_volume                     3514(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5086
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             1624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.429
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'Rigaku CrystalClear-SM Expert 2.0 r7'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ CCD (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8779
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.581
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3988
_reflns_number_gt                3435
_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       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+4.5262P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3988
_refine_ls_number_parameters     215
_refine_ls_number_restraints     173
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.084
_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
Zn1 Zn 0.99408(2) 0.74192(4) 0.17986(2) 0.01404(11) Uani 1 1 d . . . . .
N1 N 0.99944(15) 0.6376(3) 0.11608(8) 0.0238(5) Uani 1 1 d D U . . .
C1 C 0.9279(5) 0.6663(17) 0.0817(3) 0.036(2) Uani 0.536(17) 1 d D U P A 1
H1 H 0.878818 0.715559 0.089955 0.044 Uiso 0.536(17) 1 calc R U P A 1
C2 C 0.9271(4) 0.624(2) 0.0350(3) 0.041(3) Uani 0.536(17) 1 d D U P A 1
H2 H 0.877532 0.642479 0.011665 0.049 Uiso 0.536(17) 1 calc R U P A 1
C3 C 0.9993(5) 0.5536(15) 0.0229(3) 0.021(2) Uani 0.536(17) 1 d D U P A 1
C4 C 1.0727(2) 0.5351(5) 0.05786(11) 0.0365(8) Uani 1 1 d D U . . .
H4 H 1.122708 0.484863 0.050950 0.044 Uiso 0.536(17) 1 calc R U P A 1
H4X H 1.125926 0.524146 0.048816 0.044 Uiso 0.464(17) 1 calc R U P A 2
C5 C 1.0701(2) 0.5918(5) 0.10250(11) 0.0330(7) Uani 1 1 d D U . . .
H5 H 1.121857 0.598462 0.124793 0.040 Uiso 1 1 calc R U . . .
C1X C 0.9291(5) 0.5815(15) 0.0879(3) 0.025(2) Uani 0.464(17) 1 d D U P A 2
H1X H 0.877209 0.585909 0.098718 0.030 Uiso 0.464(17) 1 calc R U P A 2
C2X C 0.9288(4) 0.5173(16) 0.0437(3) 0.025(2) Uani 0.464(17) 1 d D U P A 2
H2X H 0.875897 0.487632 0.024408 0.030 Uiso 0.464(17) 1 calc R U P A 2
C3X C 1.0003(6) 0.4942(15) 0.0263(4) 0.023(2) Uani 0.464(17) 1 d D . P A 2
C6 C 0.74884(15) 0.6138(3) 0.19877(9) 0.0133(5) Uani 1 1 d . . . . .
C7 C 0.71004(16) 0.7746(3) 0.18741(9) 0.0137(5) Uani 1 1 d . . . . .
H7 H 0.740549 0.866619 0.176394 0.016 Uiso 1 1 calc R U . . .
C8 C 0.62673(16) 0.8017(3) 0.19208(9) 0.0149(5) Uani 1 1 d . . . . .
C9 C 0.58196(16) 0.6664(3) 0.20805(9) 0.0139(5) Uani 1 1 d . . . . .
H9 H 0.524484 0.683082 0.210304 0.017 Uiso 1 1 calc R U . . .
C10 C 0.62155(15) 0.5069(3) 0.22071(9) 0.0138(5) Uani 1 1 d . . . . .
C11 C 0.70479(15) 0.4794(3) 0.21588(9) 0.0139(5) Uani 1 1 d . . . . .
H11 H 0.731453 0.369943 0.224183 0.017 Uiso 1 1 calc R U . . .
C12 C 0.84080(16) 0.5889(3) 0.19562(9) 0.0150(5) Uani 1 1 d . . . . .
O1 O 0.87408(11) 0.7236(2) 0.17952(7) 0.0172(4) Uani 1 1 d . . . . .
O2 O 0.87778(12) 0.4511(2) 0.20800(7) 0.0196(4) Uani 1 1 d . . . . .
C13 C 0.58795(16) 0.9794(3) 0.18230(9) 0.0164(5) Uani 1 1 d . . . . .
O3 O 0.63054(12) 1.1009(2) 0.17082(7) 0.0213(4) Uani 1 1 d . . . . .
O4 O 0.51062(11) 1.0000(2) 0.18735(6) 0.0162(4) Uani 1 1 d . . . . .
N2 N 0.57289(14) 0.3690(3) 0.23609(8) 0.0146(4) Uani 1 1 d D . . . .
H2A H 0.6026(17) 0.283(3) 0.2487(10) 0.017 Uiso 1 1 d D U . . .
H2B H 0.5449(17) 0.413(4) 0.2542(9) 0.017 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.9366(19) . ?
Zn1 O4 1.998(2) 6_675 ?
Zn1 N1 2.038(2) . ?
Zn1 N2 2.044(2) 6_665 ?
N1 C5 1.324(4) . ?
N1 C1X 1.330(7) . ?
N1 C1 1.384(7) . ?
C1 C2 1.394(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(8) . ?
C3 C3 1.569(17) 5_765 ?
C4 C3X 1.369(10) . ?
C4 C5 1.378(4) . ?
C4 H4 0.9500 . ?
C4 H4X 0.9500 . ?
C5 H5 0.9500 . ?
C1X C2X 1.376(9) . ?
C1X H1X 0.9500 . ?
C2X C3X 1.361(10) . ?
C2X H2X 0.9500 . ?
C3X C3X 1.53(2) 5_765 ?
C6 C7 1.389(4) . ?
C6 C11 1.397(3) . ?
C6 C12 1.515(3) . ?
C7 C8 1.391(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(3) . ?
C8 C13 1.499(4) . ?
C9 C10 1.392(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(3) . ?
C10 N2 1.438(3) . ?
C11 H11 0.9500 . ?
C12 O2 1.229(3) . ?
C12 O1 1.292(3) . ?
C13 O3 1.240(3) . ?
C13 O4 1.293(3) . ?
N2 H2A 0.850(18) . ?
N2 H2B 0.830(17) . ?

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 O4 100.55(7) . 6_675 ?
O1 Zn1 N1 101.05(9) . . ?
O4 Zn1 N1 117.20(9) 6_675 . ?
O1 Zn1 N2 115.69(9) . 6_665 ?
O4 Zn1 N2 105.96(8) 6_675 6_665 ?
N1 Zn1 N2 115.70(10) . 6_665 ?
C5 N1 C1X 114.1(4) . . ?
C5 N1 C1 117.8(4) . . ?
C5 N1 Zn1 124.8(2) . . ?
C1X N1 Zn1 120.0(4) . . ?
C1 N1 Zn1 114.6(3) . . ?
N1 C1 C2 120.8(6) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 119.5(7) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 118.8(7) . . ?
C2 C3 C3 124.9(8) . 5_765 ?
C4 C3 C3 114.2(8) . 5_765 ?
C3X C4 C5 121.5(5) . . ?
C5 C4 C3 118.1(4) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C3X C4 H4X 119.3 . . ?
C5 C4 H4X 119.3 . . ?
N1 C5 C4 123.7(3) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
N1 C1X C2X 122.2(6) . . ?
N1 C1X H1X 118.9 . . ?
C2X C1X H1X 118.9 . . ?
C3X C2X C1X 123.5(7) . . ?
C3X C2X H2X 118.3 . . ?
C1X C2X H2X 118.3 . . ?
C2X C3X C4 112.9(8) . . ?
C4 C3X C3X 119.5(10) . 5_765 ?
C7 C6 C11 120.0(2) . . ?
C7 C6 C12 119.7(2) . . ?
C11 C6 C12 120.1(2) . . ?
C6 C7 C8 120.3(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 119.8(2) . . ?
C7 C8 C13 119.3(2) . . ?
C9 C8 C13 120.8(2) . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 N2 118.4(2) . . ?
C11 C10 N2 121.1(2) . . ?
C10 C11 C6 119.6(2) . . ?
C10 C11 H11 120.2 . . ?
C6 C11 H11 120.2 . . ?
O2 C12 O1 125.3(2) . . ?
O2 C12 C6 120.9(2) . . ?
O1 C12 C6 113.8(2) . . ?
C12 O1 Zn1 122.84(17) . . ?
O3 C13 O4 122.5(2) . . ?
O3 C13 C8 119.9(2) . . ?
O4 C13 C8 117.6(2) . . ?
C13 O4 Zn1 102.62(16) . 6_575 ?
C10 N2 Zn1 110.20(16) . 6_565 ?
C10 N2 H2A 114(2) . . ?
Zn1 N2 H2A 103(2) 6_565 . ?
C10 N2 H2B 108(2) . . ?
Zn1 N2 H2B 110(2) 6_565 . ?
H2A N2 H2B 112(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 9.2(9) . . . . ?
Zn1 N1 C1 C2 171.2(5) . . . . ?
N1 C1 C2 C3 -0.8(10) . . . . ?
C1 C2 C3 C4 -2.9(11) . . . . ?
C1 C2 C3 C3 159.6(12) . . . 5_765 ?
C2 C3 C4 C5 -1.7(9) . . . . ?
C3 C3 C4 C5 -165.9(8) 5_765 . . . ?
C1X N1 C5 C4 17.2(7) . . . . ?
C1 N1 C5 C4 -14.5(8) . . . . ?
Zn1 N1 C5 C4 -174.4(3) . . . . ?
C3X C4 C5 N1 -11.1(8) . . . . ?
C3 C4 C5 N1 10.8(8) . . . . ?
C5 N1 C1X C2X -14.0(8) . . . . ?
Zn1 N1 C1X C2X 177.0(5) . . . . ?
N1 C1X C2X C3X 4.7(11) . . . . ?
C1X C2X C3X C4 2.3(11) . . . . ?
C1X C2X C3X C3X -151.1(12) . . . 5_765 ?
C5 C4 C3X C2X 0.6(10) . . . . ?
C5 C4 C3X C3X 154.7(10) . . . 5_765 ?
C11 C6 C7 C8 -1.3(4) . . . . ?
C12 C6 C7 C8 -177.2(2) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C6 C7 C8 C13 176.4(2) . . . . ?
C7 C8 C9 C10 2.1(4) . . . . ?
C13 C8 C9 C10 -174.5(2) . . . . ?
C8 C9 C10 C11 -2.4(4) . . . . ?
C8 C9 C10 N2 -178.7(2) . . . . ?
C9 C10 C11 C6 0.8(4) . . . . ?
N2 C10 C11 C6 177.0(2) . . . . ?
C7 C6 C11 C10 1.1(4) . . . . ?
C12 C6 C11 C10 176.9(2) . . . . ?
C7 C6 C12 O2 175.9(2) . . . . ?
C11 C6 C12 O2 0.0(4) . . . . ?
C7 C6 C12 O1 -3.7(3) . . . . ?
C11 C6 C12 O1 -179.5(2) . . . . ?
O2 C12 O1 Zn1 -8.4(4) . . . . ?
C6 C12 O1 Zn1 171.08(16) . . . . ?
C7 C8 C13 O3 -1.0(4) . . . . ?
C9 C8 C13 O3 175.7(2) . . . . ?
C7 C8 C13 O4 -179.5(2) . . . . ?
C9 C8 C13 O4 -2.8(4) . . . . ?
O3 C13 O4 Zn1 -6.3(3) . . . 6_575 ?
C8 C13 O4 Zn1 172.13(19) . . . 6_575 ?
C9 C10 N2 Zn1 76.7(2) . . . 6_565 ?
C11 C10 N2 Zn1 -99.6(2) . . . 6_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2A O2 0.850(18) 2.18(2) 2.959(3) 153(3) 7_655 yes
N2 H2B O4 0.830(17) 2.179(19) 2.997(3) 168(3) 4_545 yes

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.092


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylformamide/methanol'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2207268'
loop_
_audit_author_name
_audit_author_address
'Mark Elsegood'
;Loughborough University
United Kingdom
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_cr501               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Weak, twinned data set of marginal quality.
;
_vrf_DIFMN02_cr501               
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00
RESPONSE: Weak, twinned data set of marginal quality.
;
_vrf_PLAT029_cr501               
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.924 Why?  
RESPONSE: No significant inetensity beyond this threshold.
;
_vrf_PLAT043_cr501               
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..      56.81 Check 
RESPONSE: Squeezed
;
_vrf_PLAT084_cr501               
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.55 Report
RESPONSE: Weak, twinned data set of marginal quality.
;
_vrf_PLAT601_cr501               
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS of .        241 Ang**3
RESPONSE: Squeezed
;
_vrf_PLAT972_cr501               
;
PROBLEM: Check Calcd Resid. Dens.  0.92Ang From Zn1            -3.70 eA-3  
RESPONSE: Weak, twinned data set of marginal quality.
;
_vrf_PLAT973_cr501               
;
PROBLEM: Check Calcd Positive Resid. Density on       Zn1       2.76 eA-3  
RESPONSE: Weak, twinned data set of marginal quality.
;
_vrf_PLAT051_cr501               
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .       5.78 %     
RESPONSE: Due to Squeezed solvent.
;
_vrf_PLAT082_cr501               
;
PROBLEM: High R1 Value ..................................       0.20 Report
RESPONSE: Weak, twinned data set of marginal quality.
;
_vrf_PLAT098_cr501               
;
PROBLEM: Large Reported Min.  (Negative) Residual Density      -3.34 eA-3  
RESPONSE: Weak, twinned data set of marginal quality.
;
_vrf_PLAT341_cr501               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01562 Ang.  
RESPONSE: Weak, twinned data set of marginal quality.
;
_vrf_PLAT911_cr501               
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.547        183 Report
RESPONSE: Reflections probably omitted due to twinning problems during data
reduction.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N3 O4 Zn, 0.75(C3 H7 N O)'
_chemical_formula_sum            'C15.25 H14.25 N3.75 O4.75 Zn'
_chemical_formula_weight         391.42

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'

_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                   15.01(3)
_cell_length_b                   7.754(19)
_cell_length_c                   16.11(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.20(3)
_cell_angle_gamma                90
_cell_volume                     1771(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1319
_cell_measurement_theta_min      21.3
_cell_measurement_theta_max      68.6

_exptl_crystal_description       Blade
_exptl_crystal_colour            'Light Brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.205
_shelx_estimated_absorpt_T_min   0.692
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.468
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn944+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 22.2222
_diffrn_reflns_number            6600
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_av_R_equivalents  0.1696
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.624
_diffrn_reflns_theta_max         57.466
_diffrn_reflns_theta_full        57.466
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 0.924
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_point_group_measured_fraction_full 0.924
_reflns_number_total             2248
_reflns_number_gt                1640
_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       
; 
Rigaku CrystalClear-SM Expert 2.0 r7 
;
_computing_cell_refinement       
; 
Rigaku CrystalClear-SM Expert 2.0 r7 
;
_computing_data_reduction        
; 
Rigaku CrystalClear-SM Expert 2.0 r7 
;
_computing_structure_solution    'SHELXLS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.4851P)²+2.7500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2248
_refine_ls_number_parameters     254
_refine_ls_number_restraints     371
_refine_ls_R_factor_all          0.2183
_refine_ls_R_factor_gt           0.2043
_refine_ls_wR_factor_ref         0.5464
_refine_ls_wR_factor_gt          0.5170
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.019
_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
Zn1 Zn 0.64175(11) 1.00022(12) 0.81489(11) 0.0485(13) Uani 1 1 d . U . . .
N1 N 0.7584(9) 0.8689(14) 0.8855(8) 0.049(3) Uani 0.799(17) 1 d D U P A 1
C1 C 0.7850(12) 0.8550(19) 0.9714(10) 0.068(4) Uani 0.799(17) 1 d D U P A 1
H1 H 0.753549 0.921570 1.002804 0.081 Uiso 0.799(17) 1 calc R U P A 1
C2 C 0.8610(12) 0.741(2) 1.0199(12) 0.086(5) Uani 0.799(17) 1 d D U P A 1
H2 H 0.876844 0.726327 1.081603 0.103 Uiso 0.799(17) 1 calc R U P A 1
C3 C 0.9071(15) 0.660(3) 0.9751(13) 0.095(6) Uani 0.799(17) 1 d D U P A 1
C4 C 0.8741(15) 0.654(3) 0.8872(12) 0.091(6) Uani 0.799(17) 1 d D U P A 1
H4 H 0.903818 0.582545 0.856121 0.109 Uiso 0.799(17) 1 calc R U P A 1
C5 C 0.7988(13) 0.749(3) 0.8432(11) 0.078(6) Uani 0.799(17) 1 d D U P A 1
H5 H 0.772037 0.735391 0.781401 0.094 Uiso 0.799(17) 1 calc R U P A 1
N2 N 0.9861(13) 0.548(3) 1.0183(12) 0.093(6) Uani 0.799(17) 1 d D U P A 1
N1X N 0.781(3) 0.908(8) 0.877(3) 0.072(10) Uani 0.201(17) 1 d D U P A 2
C1X C 0.831(3) 0.940(7) 0.959(3) 0.065(9) Uani 0.201(17) 1 d D U P A 2
H1X H 0.806461 1.020190 0.990722 0.078 Uiso 0.201(17) 1 calc R U P A 2
C2X C 0.921(3) 0.859(7) 1.004(3) 0.079(9) Uani 0.201(17) 1 d D U P A 2
H2X H 0.954538 0.884248 1.064087 0.094 Uiso 0.201(17) 1 calc R U P A 2
C3X C 0.954(4) 0.749(9) 0.960(3) 0.090(9) Uani 0.201(17) 1 d D U P A 2
C4X C 0.906(5) 0.714(10) 0.876(3) 0.090(11) Uani 0.201(17) 1 d D U P A 2
H4X H 0.926810 0.625006 0.846426 0.108 Uiso 0.201(17) 1 calc R U P A 2
C5X C 0.827(4) 0.802(10) 0.833(3) 0.076(10) Uani 0.201(17) 1 d D U P A 2
H5X H 0.802351 0.792979 0.770855 0.091 Uiso 0.201(17) 1 calc R U P A 2
N2X N 1.042(4) 0.658(10) 0.999(5) 0.11(2) Uani 0.201(17) 1 d D U P A 2
C6 C 0.6035(7) 0.8592(11) 0.5508(7) 0.047(3) Uani 1 1 d . . . . .
C7 C 0.6238(8) 1.0202(13) 0.5208(11) 0.055(4) Uani 1 1 d . . . . .
H7 H 0.644350 1.112436 0.561472 0.065 Uiso 1 1 calc R U . . .
C8 C 0.6147(8) 1.0468(15) 0.4346(9) 0.053(3) Uani 1 1 d . . . . .
C9 C 0.5825(7) 0.9111(11) 0.3737(6) 0.044(3) Uani 1 1 d . . . . .
H9 H 0.576588 0.928213 0.313739 0.053 Uiso 1 1 calc R U . . .
C10 C 0.5595(7) 0.7535(11) 0.4011(6) 0.041(2) Uani 1 1 d . . . . .
C11 C 0.5700(7) 0.7306(11) 0.4865(7) 0.046(3) Uani 1 1 d . . . . .
H11 H 0.553958 0.621535 0.504437 0.055 Uiso 1 1 calc R U . . .
C12 C 0.6110(8) 0.8381(12) 0.6434(8) 0.051(3) Uani 1 1 d . . . . .
O1 O 0.6412(6) 0.9738(8) 0.6947(6) 0.043(2) Uani 1 1 d . . . . .
O2 O 0.5893(5) 0.6997(8) 0.6707(4) 0.053(2) Uani 1 1 d . . . . .
C13 C 0.6361(8) 1.2211(12) 0.4026(7) 0.049(3) Uani 1 1 d . . . . .
O3 O 0.6569(6) 1.3436(8) 0.4571(5) 0.055(2) Uani 1 1 d . . . . .
O4 O 0.6264(5) 1.2445(8) 0.3212(5) 0.049(2) Uani 1 1 d . . . . .
N3 N 0.5261(6) 0.6148(9) 0.3364(5) 0.046(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.944(9) . ?
Zn1 O4 1.999(8) 4_586 ?
Zn1 N1 2.022(12) . ?
Zn1 N3 2.080(10) 4_576 ?
Zn1 N1X 2.13(4) . ?
Zn1 C13 2.599(11) 4_586 ?
N1 C1 1.313(18) . ?
N1 C5 1.400(17) . ?
C1 C2 1.45(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.32(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.34(2) . ?
C3 N2 1.45(2) . ?
C4 C5 1.34(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
N2 N2 1.12(3) 3_767 ?
N1X C1X 1.32(2) . ?
N1X C5X 1.40(2) . ?
C1X C2X 1.45(3) . ?
C1X H1X 0.9500 . ?
C2X C3X 1.31(3) . ?
C2X H2X 0.9500 . ?
C3X C4X 1.34(3) . ?
C3X N2X 1.44(3) . ?
C4X C5X 1.34(3) . ?
C4X H4X 0.9500 . ?
C5X H5X 0.9500 . ?
C6 C11 1.407(15) . ?
C6 C7 1.408(15) . ?
C6 C12 1.467(16) . ?
C7 C8 1.37(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.412(17) . ?
C8 C13 1.517(17) . ?
C9 C10 1.381(13) . ?
C9 H9 0.9500 . ?
C10 C11 1.344(15) . ?
C10 N3 1.467(12) . ?
C11 H11 0.9500 . ?
C12 O2 1.243(12) . ?
C12 O1 1.323(13) . ?
C13 O3 1.261(12) . ?
C13 O4 1.285(13) . ?

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 O4 101.1(3) . 4_586 ?
O1 Zn1 N1 103.1(5) . . ?
O4 Zn1 N1 124.3(4) 4_586 . ?
O1 Zn1 N3 113.0(3) . 4_576 ?
O4 Zn1 N3 107.5(3) 4_586 4_576 ?
N1 Zn1 N3 107.9(5) . 4_576 ?
O1 Zn1 N1X 96.4(15) . . ?
O4 Zn1 N1X 114.9(17) 4_586 . ?
N3 Zn1 N1X 122(2) 4_576 . ?
O1 Zn1 C13 129.7(3) . 4_586 ?
O4 Zn1 C13 28.9(3) 4_586 4_586 ?
N1 Zn1 C13 106.9(4) . 4_586 ?
N3 Zn1 C13 95.0(4) 4_576 4_586 ?
C1 N1 C5 115.3(12) . . ?
C1 N1 Zn1 122.8(10) . . ?
C5 N1 Zn1 119.6(9) . . ?
N1 C1 C2 122.0(14) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 117.4(16) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.2(16) . . ?
C2 C3 N2 121.2(18) . . ?
C4 C3 N2 116.7(18) . . ?
C3 C4 C5 119.7(16) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 N1 122.2(14) . . ?
C4 C5 H5 118.9 . . ?
N1 C5 H5 118.9 . . ?
N2 N2 C3 122(2) 3_767 . ?
C1X N1X C5X 114(2) . . ?
C1X N1X Zn1 123(3) . . ?
C5X N1X Zn1 122(3) . . ?
N1X C1X C2X 123(3) . . ?
N1X C1X H1X 118.4 . . ?
C2X C1X H1X 118.4 . . ?
C3X C2X C1X 118(3) . . ?
C3X C2X H2X 121.0 . . ?
C1X C2X H2X 121.0 . . ?
C2X C3X C4X 120(3) . . ?
C2X C3X N2X 123(3) . . ?
C4X C3X N2X 117(3) . . ?
C3X C4X C5X 121(3) . . ?
C3X C4X H4X 119.5 . . ?
C5X C4X H4X 119.5 . . ?
C4X C5X N1X 122(3) . . ?
C4X C5X H5X 118.8 . . ?
N1X C5X H5X 118.8 . . ?
C11 C6 C7 116.2(11) . . ?
C11 C6 C12 123.9(9) . . ?
C7 C6 C12 119.7(10) . . ?
C8 C7 C6 121.5(12) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 119.4(11) . . ?
C7 C8 C13 121.2(11) . . ?
C9 C8 C13 119.4(11) . . ?
C10 C9 C8 120.1(10) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 119.1(8) . . ?
C11 C10 N3 121.9(8) . . ?
C9 C10 N3 119.0(9) . . ?
C10 C11 C6 123.6(8) . . ?
C10 C11 H11 118.2 . . ?
C6 C11 H11 118.2 . . ?
O2 C12 O1 122.7(10) . . ?
O2 C12 C6 121.0(9) . . ?
O1 C12 C6 116.2(9) . . ?
C12 O1 Zn1 126.5(7) . . ?
O3 C13 O4 121.6(9) . . ?
O3 C13 C8 117.7(10) . . ?
O4 C13 C8 120.5(9) . . ?
O3 C13 Zn1 73.0(6) . 4_585 ?
O4 C13 Zn1 48.7(4) . 4_585 ?
C8 C13 Zn1 166.8(8) . 4_585 ?
C13 O4 Zn1 102.4(6) . 4_585 ?
C10 N3 Zn1 108.9(6) . 4_575 ?

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
C5 N1 C1 C2 8.7(19) . . . . ?
Zn1 N1 C1 C2 171.3(11) . . . . ?
N1 C1 C2 C3 4(2) . . . . ?
C1 C2 C3 C4 -13(3) . . . . ?
C1 C2 C3 N2 178(2) . . . . ?
C2 C3 C4 C5 8(4) . . . . ?
N2 C3 C4 C5 178(2) . . . . ?
C3 C4 C5 N1 6(4) . . . . ?
C1 N1 C5 C4 -14(3) . . . . ?
Zn1 N1 C5 C4 -177.4(17) . . . . ?
C2 C3 N2 N2 163(4) . . . 3_767 ?
C4 C3 N2 N2 -7(5) . . . 3_767 ?
C5X N1X C1X C2X -6(4) . . . . ?
Zn1 N1X C1X C2X 171(4) . . . . ?
N1X C1X C2X C3X 0(5) . . . . ?
C1X C2X C3X C4X 0(10) . . . . ?
C1X C2X C3X N2X -179(6) . . . . ?
C2X C3X C4X C5X 7(13) . . . . ?
N2X C3X C4X C5X -174(8) . . . . ?
C3X C4X C5X N1X -14(12) . . . . ?
C1X N1X C5X C4X 13(9) . . . . ?
Zn1 N1X C5X C4X -165(7) . . . . ?
C11 C6 C7 C8 -2.4(17) . . . . ?
C12 C6 C7 C8 -177.8(11) . . . . ?
C6 C7 C8 C9 1.3(18) . . . . ?
C6 C7 C8 C13 179.6(10) . . . . ?
C7 C8 C9 C10 0.6(16) . . . . ?
C13 C8 C9 C10 -177.7(9) . . . . ?
C8 C9 C10 C11 -1.3(15) . . . . ?
C8 C9 C10 N3 179.9(9) . . . . ?
C9 C10 C11 C6 0.0(16) . . . . ?
N3 C10 C11 C6 178.8(10) . . . . ?
C7 C6 C11 C10 1.8(16) . . . . ?
C12 C6 C11 C10 177.0(10) . . . . ?
C11 C6 C12 O2 1.6(17) . . . . ?
C7 C6 C12 O2 176.7(10) . . . . ?
C11 C6 C12 O1 -177.9(10) . . . . ?
C7 C6 C12 O1 -2.9(16) . . . . ?
O2 C12 O1 Zn1 -9.1(15) . . . . ?
C6 C12 O1 Zn1 170.5(7) . . . . ?
C7 C8 C13 O3 -4.3(16) . . . . ?
C9 C8 C13 O3 174.0(10) . . . . ?
C7 C8 C13 O4 -179.4(11) . . . . ?
C9 C8 C13 O4 -1.1(16) . . . . ?
C7 C8 C13 Zn1 -147(3) . . . 4_585 ?
C9 C8 C13 Zn1 31(4) . . . 4_585 ?
O3 C13 O4 Zn1 -4.3(12) . . . 4_585 ?
C8 C13 O4 Zn1 170.6(8) . . . 4_585 ?
C11 C10 N3 Zn1 -98.5(10) . . . 4_575 ?
C9 C10 N3 Zn1 80.3(9) . . . 4_575 ?

_refine_diff_density_max         2.080
_refine_diff_density_min         -3.342
_refine_diff_density_rms         0.268


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylformamide/methanol'
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2207277'
loop_
_audit_author_name
_audit_author_address
'Mark Elsegood'
;Loughborough University
United Kingdom
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2022-12-06 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         'C16 H16 Cd N4 O5'
_chemical_formula_sum            'C16 H16 Cd N4 O5'
_chemical_formula_weight         456.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 '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                   8.1035(15)
_cell_length_b                   8.1227(15)
_cell_length_c                   13.739(3)
_cell_angle_alpha                89.277(3)
_cell_angle_beta                 84.236(3)
_cell_angle_gamma                77.887(3)
_cell_volume                     879.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2981
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      27.13

_exptl_crystal_description       tablet
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.277
_shelx_estimated_absorpt_T_min   0.767
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   'TWINABS v2012/1, Sheldrick, G.M., (2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17030
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.565
_diffrn_reflns_theta_max         28.387
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4354
_reflns_number_gt                3727
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'Bruker APEX 2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0384P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4354
_refine_ls_number_parameters     244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0743
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.09514(3) 0.05402(3) 0.83220(2) 0.02022(7) Uani 1 1 d . . . . .
N1 N 0.2507(4) 0.1934(4) 0.72140(19) 0.0261(6) Uani 1 1 d . . . . .
C1 C 0.3980(5) 0.1143(5) 0.6768(3) 0.0378(9) Uani 1 1 d . . . . .
H1 H 0.438455 -0.000912 0.691212 0.045 Uiso 1 1 calc R U . . .
C2 C 0.4956(6) 0.1924(5) 0.6099(3) 0.0408(10) Uani 1 1 d . . . . .
H2 H 0.600724 0.132031 0.579168 0.049 Uiso 1 1 calc R U . . .
C3 C 0.4366(5) 0.3595(5) 0.5890(2) 0.0299(7) Uani 1 1 d . . . . .
C4 C 0.2861(5) 0.4459(5) 0.6376(3) 0.0333(9) Uani 1 1 d . . . . .
H4 H 0.245187 0.562342 0.626393 0.040 Uiso 1 1 calc R U . . .
C5 C 0.1971(5) 0.3576(5) 0.7029(2) 0.0295(7) Uani 1 1 d . . . . .
H5 H 0.093262 0.415758 0.736209 0.035 Uiso 1 1 calc R U . . .
N2 N 0.5388(4) 0.4341(4) 0.5176(2) 0.0327(6) Uani 1 1 d . . . . .
C6 C -0.4213(5) 0.3132(5) 0.8856(3) 0.0203(7) Uani 1 1 d . . . . .
C7 C -0.4834(5) 0.4845(4) 0.8702(2) 0.0204(6) Uani 1 1 d . . . . .
H7 H -0.407777 0.554233 0.846698 0.024 Uiso 1 1 calc R U . . .
C8 C -0.6548(5) 0.5526(4) 0.8893(2) 0.0186(7) Uani 1 1 d . . . . .
C9 C -0.7661(4) 0.4492(4) 0.9257(2) 0.0206(7) Uani 1 1 d . . . . .
H9 H -0.883675 0.495915 0.939602 0.025 Uiso 1 1 calc R U . . .
C10 C -0.7043(4) 0.2792(4) 0.9413(2) 0.0215(6) Uani 1 1 d . . . . .
C11 C -0.5316(4) 0.2114(4) 0.9201(2) 0.0211(7) Uani 1 1 d . . . . .
H11 H -0.489241 0.094687 0.929312 0.025 Uiso 1 1 calc R U . . .
C12 C -0.2357(4) 0.2377(4) 0.8627(3) 0.0220(8) Uani 1 1 d . . . . .
O1 O -0.1871(3) 0.0821(3) 0.8804(2) 0.0278(6) Uani 1 1 d . . . . .
O2 O -0.1339(3) 0.3244(3) 0.8276(2) 0.0327(7) Uani 1 1 d . . . . .
C13 C -0.7268(5) 0.7334(4) 0.8686(3) 0.0216(8) Uani 1 1 d . . . . .
O3 O -0.6340(3) 0.8239(3) 0.8275(2) 0.0289(6) Uani 1 1 d . . . . .
O4 O -0.8841(3) 0.7864(3) 0.8907(2) 0.0276(6) Uani 1 1 d . . . . .
N3 N -0.8180(4) 0.1712(4) 0.96905(19) 0.0219(5) Uani 1 1 d D . . . .
H3A H -0.905(4) 0.222(4) 0.998(3) 0.026 Uiso 1 1 d D U . . .
H3B H -0.775(5) 0.091(4) 0.999(3) 0.026 Uiso 1 1 d D U . . .
O5 O 0.0346(4) -0.0649(4) 0.68319(19) 0.0448(7) Uani 1 1 d . . . . .
C14 C -0.0736(6) -0.1501(6) 0.6967(3) 0.0435(9) Uani 1 1 d . . . . .
H14 H -0.122309 -0.159174 0.761896 0.052 Uiso 1 1 calc R U . . .
N4 N -0.1277(5) -0.2309(5) 0.6265(2) 0.0467(9) Uani 1 1 d . . . . .
C15 C -0.2598(8) -0.3268(8) 0.6477(4) 0.0707(15) Uani 1 1 d . . . . .
H15A H -0.304826 -0.310860 0.716651 0.106 Uiso 1 1 calc R U . . .
H15B H -0.212064 -0.446503 0.634678 0.106 Uiso 1 1 calc R U . . .
H15C H -0.351372 -0.287456 0.606147 0.106 Uiso 1 1 calc R U . . .
C16 C -0.0561(7) -0.2231(7) 0.5257(3) 0.0609(15) Uani 1 1 d . . . . .
H16A H -0.138363 -0.148806 0.488564 0.091 Uiso 1 1 calc R U . . .
H16B H -0.029436 -0.336269 0.496569 0.091 Uiso 1 1 calc R U . . .
H16C H 0.047795 -0.178947 0.523938 0.091 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 O1 2.281(3) . ?
Cd1 O4 2.287(3) 1_645 ?
Cd1 N1 2.315(2) . ?
Cd1 N3 2.351(3) 1_655 ?
Cd1 O5 2.411(3) . ?
Cd1 O3 2.563(2) 1_645 ?
Cd1 O2 2.565(3) . ?
N1 C1 1.324(5) . ?
N1 C5 1.342(5) . ?
C1 C2 1.386(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.378(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(6) . ?
C3 N2 1.431(4) . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
N2 N2 1.241(7) 2_666 ?
C6 C11 1.386(5) . ?
C6 C7 1.398(5) . ?
C6 C12 1.504(5) . ?
C7 C8 1.382(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.409(4) . ?
C8 C13 1.497(5) . ?
C9 C10 1.388(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.395(5) . ?
C10 N3 1.422(4) . ?
C11 H11 0.9500 . ?
C12 O2 1.251(5) . ?
C12 O1 1.271(4) . ?
C13 O3 1.249(4) . ?
C13 O4 1.265(4) . ?
N3 H3A 0.81(2) . ?
N3 H3B 0.80(2) . ?
O5 C14 1.225(5) . ?
C14 N4 1.333(5) . ?
C14 H14 0.9500 . ?
N4 C16 1.453(5) . ?
N4 C15 1.455(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 O4 84.33(7) . 1_645 ?
O1 Cd1 N1 134.16(11) . . ?
O4 Cd1 N1 137.12(11) 1_645 . ?
O1 Cd1 N3 100.12(10) . 1_655 ?
O4 Cd1 N3 97.27(10) 1_645 1_655 ?
N1 Cd1 N3 93.57(9) . 1_655 ?
O1 Cd1 O5 85.73(10) . . ?
O4 Cd1 O5 84.45(11) 1_645 . ?
N1 Cd1 O5 81.37(9) . . ?
N3 Cd1 O5 174.02(9) 1_655 . ?
O1 Cd1 O3 137.96(8) . 1_645 ?
O4 Cd1 O3 53.67(8) 1_645 1_645 ?
N1 Cd1 O3 85.49(10) . 1_645 ?
N3 Cd1 O3 88.35(11) 1_655 1_645 ?
O5 Cd1 O3 88.07(11) . 1_645 ?
O1 Cd1 O2 53.64(8) . . ?
O4 Cd1 O2 137.71(9) 1_645 . ?
N1 Cd1 O2 84.04(11) . . ?
N3 Cd1 O2 87.01(11) 1_655 . ?
O5 Cd1 O2 95.58(11) . . ?
O3 Cd1 O2 168.26(6) 1_645 . ?
C1 N1 C5 118.2(3) . . ?
C1 N1 Cd1 120.7(2) . . ?
C5 N1 Cd1 121.1(2) . . ?
N1 C1 C2 122.8(4) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 118.5(4) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 N2 116.8(4) . . ?
C4 C3 N2 123.7(4) . . ?
C5 C4 C3 117.9(4) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
N1 C5 C4 123.0(4) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
N2 N2 C3 113.7(4) 2_666 . ?
C11 C6 C7 120.0(3) . . ?
C11 C6 C12 119.7(3) . . ?
C7 C6 C12 120.3(3) . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 119.7(3) . . ?
C7 C8 C13 121.4(3) . . ?
C9 C8 C13 118.8(3) . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.5(3) . . ?
C9 C10 N3 120.3(3) . . ?
C11 C10 N3 119.9(3) . . ?
C6 C11 C10 120.5(3) . . ?
C6 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
O2 C12 O1 121.6(3) . . ?
O2 C12 C6 121.4(3) . . ?
O1 C12 C6 117.0(3) . . ?
C12 O1 Cd1 98.8(2) . . ?
C12 O2 Cd1 86.0(2) . . ?
O3 C13 O4 122.5(3) . . ?
O3 C13 C8 120.2(3) . . ?
O4 C13 C8 117.3(3) . . ?
C13 O3 Cd1 85.7(2) . 1_465 ?
C13 O4 Cd1 98.2(2) . 1_465 ?
C10 N3 Cd1 111.80(19) . 1_455 ?
C10 N3 H3A 112(3) . . ?
Cd1 N3 H3A 104(3) 1_455 . ?
C10 N3 H3B 113(3) . . ?
Cd1 N3 H3B 104(3) 1_455 . ?
H3A N3 H3B 112(3) . . ?
C14 O5 Cd1 113.0(2) . . ?
O5 C14 N4 124.6(4) . . ?
O5 C14 H14 117.7 . . ?
N4 C14 H14 117.7 . . ?
C14 N4 C16 120.1(4) . . ?
C14 N4 C15 121.6(4) . . ?
C16 N4 C15 118.3(4) . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -2.1(6) . . . . ?
Cd1 N1 C1 C2 180.0(3) . . . . ?
N1 C1 C2 C3 0.0(7) . . . . ?
C1 C2 C3 C4 2.4(6) . . . . ?
C1 C2 C3 N2 -178.3(4) . . . . ?
C2 C3 C4 C5 -2.6(6) . . . . ?
N2 C3 C4 C5 178.2(3) . . . . ?
C1 N1 C5 C4 1.9(6) . . . . ?
Cd1 N1 C5 C4 179.8(3) . . . . ?
C3 C4 C5 N1 0.4(6) . . . . ?
C2 C3 N2 N2 161.4(4) . . . 2_666 ?
C4 C3 N2 N2 -19.4(6) . . . 2_666 ?
C11 C6 C7 C8 -0.1(5) . . . . ?
C12 C6 C7 C8 178.5(3) . . . . ?
C6 C7 C8 C9 1.0(4) . . . . ?
C6 C7 C8 C13 -176.7(3) . . . . ?
C7 C8 C9 C10 -0.8(5) . . . . ?
C13 C8 C9 C10 177.0(3) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C8 C9 C10 N3 -174.0(3) . . . . ?
C7 C6 C11 C10 -1.1(5) . . . . ?
C12 C6 C11 C10 -179.7(3) . . . . ?
C9 C10 C11 C6 1.3(5) . . . . ?
N3 C10 C11 C6 175.0(3) . . . . ?
C11 C6 C12 O2 176.9(4) . . . . ?
C7 C6 C12 O2 -1.6(6) . . . . ?
C11 C6 C12 O1 -3.0(6) . . . . ?
C7 C6 C12 O1 178.5(3) . . . . ?
O2 C12 O1 Cd1 0.7(4) . . . . ?
C6 C12 O1 Cd1 -179.4(3) . . . . ?
O1 C12 O2 Cd1 -0.6(4) . . . . ?
C6 C12 O2 Cd1 179.5(3) . . . . ?
C7 C8 C13 O3 4.7(5) . . . . ?
C9 C8 C13 O3 -173.1(3) . . . . ?
C7 C8 C13 O4 -178.1(3) . . . . ?
C9 C8 C13 O4 4.1(5) . . . . ?
O4 C13 O3 Cd1 -0.4(4) . . . 1_465 ?
C8 C13 O3 Cd1 176.6(3) . . . 1_465 ?
O3 C13 O4 Cd1 0.4(4) . . . 1_465 ?
C8 C13 O4 Cd1 -176.7(3) . . . 1_465 ?
C9 C10 N3 Cd1 89.4(3) . . . 1_455 ?
C11 C10 N3 Cd1 -84.2(3) . . . 1_455 ?
Cd1 O5 C14 N4 -179.1(4) . . . . ?
O5 C14 N4 C16 0.8(8) . . . . ?
O5 C14 N4 C15 -178.5(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3A O4 0.81(2) 2.19(3) 2.897(4) 147(4) 2_367 yes
N3 H3B O1 0.80(2) 2.20(3) 2.896(4) 146(4) 2_457 yes
C5 H5 O2 0.95 2.37 3.094(4) 133.0 . yes
C1 H1 O3 0.95 2.44 3.154(4) 132.1 1_645 yes
C14 H14 O1 0.95 2.50 3.114(5) 122.5 . yes

_refine_diff_density_max         1.058
_refine_diff_density_min         -0.781
_refine_diff_density_rms         0.105



#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylformamide/methanol'
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2207270'
loop_
_audit_author_name
_audit_author_address
'Mark Elsegood'
;Loughborough University
United Kingdom
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT082_cr471               
;
PROBLEM: High R1 Value ..................................       0.16 Report
RESPONSE: Twinning problems & disorder led to marginal data quality.
;
_vrf_PLAT084_cr471               
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.45 Report
RESPONSE: Twinning problems & disorder led to marginal data quality.
;
_vrf_PLAT097_cr471               
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       2.81 eA-3  
RESPONSE: Twinning problems & disorder led to marginal data quality.
;
_vrf_PLAT213_cr471               
;
PROBLEM: Atom O3              has ADP max/min Ratio .....        4.1 prolat
RESPONSE: Twinning problems & disorder led to marginal data quality.
;
_vrf_PLAT341_cr471               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01667 Ang.  
RESPONSE: Twinning problems & disorder led to marginal data quality.
;
_vrf_PLAT430_cr471               
;
PROBLEM: Short Inter D...A Contact  O7       ..N5       .       2.86 Ang.  
RESPONSE: Two DMFs are genuinely close in space.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H15 Co N3 O4, 2(C3 H7 N O)'
_chemical_formula_sum            'C26 H29 Co N5 O6'
_chemical_formula_weight         566.47

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

_space_group_crystal_system      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                   13.726(13)
_cell_length_b                   16.881(14)
_cell_length_c                   14.234(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.396(19)
_cell_angle_gamma                90
_cell_volume                     3195(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6667
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      31.0

_exptl_crystal_description       rod
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_F_000             1180
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.578
_shelx_estimated_absorpt_T_min   0.802
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  Confocal
_diffrn_detector                 CCD
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;

_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            16336
_diffrn_reflns_av_unetI/netI     0.0928
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.859
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             7669
_reflns_number_gt                5861
_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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       
; 
Rigaku CrystalClear-SM Expert 2.0 r11 
;
_computing_cell_refinement       
; 
Rigaku CrystalClear-SM Expert 2.0 r11 
;
_computing_data_reduction        
; 
Rigaku CrystalClear-SM Expert 2.0 r11 
;
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;Refined as a 2-component twin with twin law 
 -1 0 0 0 -1 0 0.516 0 1 and component ratio 0.0410:0.959(18).,Twin
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1548P)²+89.7260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7669
_refine_ls_number_parameters     428
_refine_ls_number_restraints     354
_refine_ls_R_factor_all          0.1781
_refine_ls_R_factor_gt           0.1640
_refine_ls_wR_factor_ref         0.4513
_refine_ls_wR_factor_gt          0.4436
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.048
_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 0.50440(10) 0.47402(7) 0.64023(9) 0.0166(4) Uani 1 1 d . . . . .
N1 N 0.3430(6) 0.4703(5) 0.6205(7) 0.0255(18) Uani 1 1 d . . . . .
C1 C 0.2848(8) 0.4146(7) 0.5732(10) 0.035(3) Uani 1 1 d . . . . .
H1 H 0.313620 0.375992 0.539743 0.042 Uiso 1 1 calc R U . . .
C2 C 0.1804(9) 0.4090(9) 0.5693(10) 0.043(3) Uani 1 1 d . . . . .
H2 H 0.140641 0.368148 0.532755 0.051 Uiso 1 1 calc R U . . .
C3 C 0.1378(9) 0.4631(8) 0.6186(9) 0.035(3) Uani 1 1 d . . . . .
C4 C 0.1997(9) 0.5247(8) 0.6695(12) 0.046(3) Uani 1 1 d . . . . .
H4 H 0.172336 0.564433 0.702703 0.056 Uiso 1 1 calc R U . . .
C5 C 0.3014(9) 0.5256(7) 0.6699(11) 0.041(3) Uani 1 1 d . . . . .
H5 H 0.343320 0.565686 0.705563 0.049 Uiso 1 1 calc R U . . .
C6 C 0.0289(8) 0.4568(8) 0.6180(10) 0.036(3) Uani 1 1 d . . . . .
H6 H -0.007405 0.415000 0.580203 0.044 Uiso 1 1 calc R U . . .
C7 C -0.0222(9) 0.5016(8) 0.6630(10) 0.038(3) Uani 1 1 d . . . . .
H7 H 0.013086 0.544062 0.700344 0.045 Uiso 1 1 calc R U . . .
C8 C -0.2879(9) 0.4232(7) 0.6170(10) 0.035(3) Uani 1 1 d . . . . .
H8 H -0.325940 0.378923 0.587059 0.042 Uiso 1 1 calc R U . . .
C9 C -0.1857(9) 0.4277(8) 0.6176(10) 0.038(3) Uani 1 1 d . . . . .
H9 H -0.154800 0.387269 0.588656 0.046 Uiso 1 1 calc R U . . .
C10 C -0.1305(9) 0.4928(7) 0.6618(9) 0.032(2) Uani 1 1 d . . . . .
C11 C -0.1799(9) 0.5502(8) 0.7019(10) 0.038(3) Uani 1 1 d . . . . .
H11 H -0.144025 0.595436 0.731879 0.046 Uiso 1 1 calc R U . . .
C12 C -0.2812(9) 0.5422(7) 0.6986(10) 0.037(3) Uani 1 1 d . . . . .
H12 H -0.313119 0.582659 0.726537 0.045 Uiso 1 1 calc R U . . .
N2 N -0.3352(6) 0.4808(5) 0.6582(7) 0.0249(18) Uani 1 1 d . . . . .
C13 C 0.5118(10) 0.3464(6) 0.8828(7) 0.030(2) Uani 1 1 d D . . . .
C14 C 0.5095(8) 0.2629(5) 0.8735(6) 0.022(2) Uani 1 1 d D . . . .
H14 H 0.515628 0.238641 0.815025 0.026 Uiso 1 1 calc R U . . .
C15 C 0.4983(8) 0.2170(5) 0.9506(7) 0.0201(19) Uani 1 1 d D . . . .
C16 C 0.504(2) 0.2513(11) 1.0416(12) 0.027(5) Uani 0.56(3) 1 d D U P A 1
H16 H 0.502071 0.218351 1.095179 0.033 Uiso 0.56(3) 1 calc R U P A 1
C17 C 0.513(2) 0.3354(10) 1.0547(12) 0.028(4) Uani 0.56(3) 1 d D U P A 1
N3 N 0.515(2) 0.3702(10) 1.1435(11) 0.036(5) Uani 0.56(3) 1 d D U P A 1
H3A H 0.522247 0.421898 1.150346 0.043 Uiso 0.56(3) 1 calc R U P A 1
H3B H 0.510160 0.340723 1.192956 0.043 Uiso 0.56(3) 1 calc R U P A 1
C18 C 0.521(2) 0.3822(11) 0.9757(11) 0.028(5) Uani 0.56(3) 1 d D U P A 1
H18 H 0.532223 0.437517 0.983768 0.034 Uiso 0.56(3) 1 calc R U P A 1
C16X C 0.474(3) 0.2513(13) 1.0316(17) 0.028(6) Uani 0.44(3) 1 d D U P A 2
H16X H 0.458877 0.217936 1.079790 0.034 Uiso 0.44(3) 1 calc R U P A 2
C17X C 0.472(3) 0.3359(12) 1.0432(15) 0.028(5) Uani 0.44(3) 1 d D U P A 2
N3X N 0.444(3) 0.3683(11) 1.1232(15) 0.034(6) Uani 0.44(3) 1 d D U P A 2
H3C H 0.432807 0.419460 1.125256 0.041 Uiso 0.44(3) 1 calc R U P A 2
H3D H 0.438599 0.337576 1.171440 0.041 Uiso 0.44(3) 1 calc R U P A 2
C18X C 0.482(3) 0.3817(13) 0.9639(16) 0.031(6) Uani 0.44(3) 1 d D U P A 2
H18X H 0.469358 0.437054 0.963510 0.037 Uiso 0.44(3) 1 calc R U P A 2
C19 C 0.5165(9) 0.3975(6) 0.7971(7) 0.027(2) Uani 1 1 d . . . . .
O1 O 0.5188(6) 0.4722(4) 0.8030(5) 0.0283(17) Uani 1 1 d . . . . .
O2 O 0.5225(6) 0.3631(4) 0.7185(5) 0.0263(16) Uani 1 1 d . . . . .
C20 C 0.4951(7) 0.1278(5) 0.9419(6) 0.0158(16) Uani 1 1 d . . . . .
O3 O 0.5053(6) 0.0978(4) 0.8623(5) 0.0236(15) Uani 1 1 d . . . . .
O4 O 0.4824(5) 0.0876(4) 1.0116(5) 0.0219(14) Uani 1 1 d . . . . .
O5 O -0.0329(15) 0.2951(14) 0.4711(17) 0.145(8) Uani 1 1 d D U . . .
C21 C -0.078(2) 0.2776(18) 0.387(2) 0.138(8) Uani 1 1 d D U . . .
H21 H -0.045622 0.277054 0.335524 0.166 Uiso 1 1 calc R U . . .
N4 N -0.1807(17) 0.2584(15) 0.3723(18) 0.132(7) Uani 1 1 d D U . . .
C22 C -0.240(2) 0.2523(17) 0.2735(19) 0.123(9) Uani 1 1 d D U . . .
H22A H -0.201699 0.273172 0.229439 0.184 Uiso 1 1 calc R U . . .
H22B H -0.302252 0.282931 0.266041 0.184 Uiso 1 1 calc R U . . .
H22C H -0.256894 0.196599 0.257868 0.184 Uiso 1 1 calc R U . . .
C23 C -0.236(2) 0.260(2) 0.449(2) 0.147(10) Uani 1 1 d D U . . .
H23A H -0.301933 0.234719 0.425130 0.221 Uiso 1 1 calc R U . . .
H23B H -0.245461 0.314947 0.467048 0.221 Uiso 1 1 calc R U . . .
H23C H -0.197660 0.231118 0.506136 0.221 Uiso 1 1 calc R U . . .
O6 O 0.102(2) 0.6184(19) 0.8489(18) 0.093(9) Uani 0.5 1 d D U P . .
C24 C 0.111(3) 0.597(3) 0.934(3) 0.118(11) Uani 0.5 1 d D U P . .
H24 H 0.065455 0.615238 0.969196 0.141 Uiso 0.5 1 calc R U P . .
N5 N 0.190(2) 0.546(3) 0.977(2) 0.127(11) Uani 0.5 1 d D U P . .
C25 C 0.205(4) 0.533(4) 1.079(3) 0.156(16) Uani 0.5 1 d D U P . .
H25A H 0.261795 0.496395 1.102075 0.235 Uiso 0.5 1 calc R U P . .
H25B H 0.218861 0.582875 1.114439 0.235 Uiso 0.5 1 calc R U P . .
H25C H 0.143951 0.508793 1.091397 0.235 Uiso 0.5 1 calc R U P . .
C26 C 0.263(3) 0.508(4) 0.930(3) 0.146(16) Uani 0.5 1 d D U P . .
H26A H 0.309948 0.475903 0.978078 0.219 Uiso 0.5 1 calc R U P . .
H26B H 0.226617 0.474503 0.876984 0.219 Uiso 0.5 1 calc R U P . .
H26C H 0.300203 0.549036 0.904785 0.219 Uiso 0.5 1 calc R U P . .
O7 O 0.045(4) 0.425(4) 0.906(4) 0.24(2) Uani 0.5 1 d D U P . .
C27 C 0.095(4) 0.389(4) 0.859(4) 0.222(19) Uani 0.5 1 d D U P . .
H27 H 0.085765 0.397741 0.791071 0.266 Uiso 0.5 1 calc R U P . .
N6 N 0.167(4) 0.334(3) 0.908(4) 0.228(19) Uani 0.5 1 d D U P . .
C28 C 0.222(5) 0.293(5) 0.850(4) 0.22(2) Uani 0.5 1 d D U P . .
H28A H 0.269686 0.255925 0.890760 0.332 Uiso 0.5 1 calc R U P . .
H28B H 0.175274 0.262723 0.798850 0.332 Uiso 0.5 1 calc R U P . .
H28C H 0.258929 0.330880 0.820082 0.332 Uiso 0.5 1 calc R U P . .
C29 C 0.180(5) 0.311(5) 1.010(4) 0.23(2) Uani 0.5 1 d D U P . .
H29A H 0.234261 0.271984 1.028539 0.339 Uiso 0.5 1 calc R U P . .
H29B H 0.197043 0.357978 1.051726 0.339 Uiso 0.5 1 calc R U P . .
H29C H 0.117297 0.287869 1.019220 0.339 Uiso 0.5 1 calc R 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
Co1 O4 2.061(7) 4_565 ?
Co1 O3 2.093(6) 2_656 ?
Co1 N2 2.156(8) 1_655 ?
Co1 O2 2.161(7) . ?
Co1 N1 2.164(8) . ?
Co1 O1 2.276(7) . ?
N1 C1 1.306(14) . ?
N1 C5 1.376(12) . ?
C1 C2 1.424(14) . ?
C1 H1 0.9500 . ?
C2 C3 1.369(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.422(18) . ?
C3 C6 1.496(15) . ?
C4 C5 1.394(16) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.303(17) . ?
C6 H6 0.9500 . ?
C7 C10 1.489(15) . ?
C7 H7 0.9500 . ?
C8 N2 1.377(13) . ?
C8 C9 1.403(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(16) . ?
C11 C12 1.387(16) . ?
C11 H11 0.9500 . ?
C12 N2 1.321(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.416(13) . ?
C13 C18 1.430(16) . ?
C13 C18X 1.444(18) . ?
C13 C19 1.508(14) . ?
C14 C15 1.383(12) . ?
C14 H14 0.9500 . ?
C15 C16X 1.401(17) . ?
C15 C16 1.403(16) . ?
C15 C20 1.511(12) . ?
C16 C17 1.432(18) . ?
C16 H16 0.9500 . ?
C17 N3 1.386(17) . ?
C17 C18 1.401(17) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
C18 H18 0.9500 . ?
C16X C17X 1.439(19) . ?
C16X H16X 0.9500 . ?
C17X N3X 1.395(19) . ?
C17X C18X 1.406(18) . ?
N3X H3C 0.8800 . ?
N3X H3D 0.8800 . ?
C18X H18X 0.9500 . ?
C19 O1 1.265(12) . ?
C19 O2 1.281(12) . ?
C20 O4 1.249(11) . ?
C20 O3 1.281(11) . ?
O5 C21 1.24(3) . ?
C21 N4 1.41(3) . ?
C21 H21 0.9500 . ?
N4 C22 1.44(3) . ?
N4 C23 1.48(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O6 C24 1.23(3) . ?
C24 N5 1.40(3) . ?
C24 H24 0.9500 . ?
N5 C25 1.44(3) . ?
N5 C26 1.48(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O7 C27 1.24(3) . ?
C27 N6 1.40(3) . ?
C27 H27 0.9500 . ?
N6 C28 1.44(3) . ?
N6 C29 1.48(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

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 Co1 O3 119.6(3) 4_565 2_656 ?
O4 Co1 N2 92.9(3) 4_565 1_655 ?
O3 Co1 N2 90.5(3) 2_656 1_655 ?
O4 Co1 O2 89.6(3) 4_565 . ?
O3 Co1 O2 150.7(3) 2_656 . ?
N2 Co1 O2 90.1(3) 1_655 . ?
O4 Co1 N1 87.2(3) 4_565 . ?
O3 Co1 N1 88.2(3) 2_656 . ?
N2 Co1 N1 178.5(3) 1_655 . ?
O2 Co1 N1 91.4(3) . . ?
O4 Co1 O1 148.6(3) 4_565 . ?
O3 Co1 O1 91.1(3) 2_656 . ?
N2 Co1 O1 93.0(3) 1_655 . ?
O2 Co1 O1 59.6(3) . . ?
N1 Co1 O1 87.6(3) . . ?
C1 N1 C5 118.2(9) . . ?
C1 N1 Co1 124.3(7) . . ?
C5 N1 Co1 117.1(7) . . ?
N1 C1 C2 123.3(11) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C3 C2 C1 119.3(11) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 118.1(11) . . ?
C2 C3 C6 120.2(11) . . ?
C4 C3 C6 121.7(11) . . ?
C5 C4 C3 118.7(12) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 122.2(11) . . ?
N1 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C7 C6 C3 127.9(12) . . ?
C7 C6 H6 116.0 . . ?
C3 C6 H6 116.0 . . ?
C6 C7 C10 126.5(12) . . ?
C6 C7 H7 116.8 . . ?
C10 C7 H7 116.8 . . ?
N2 C8 C9 122.4(11) . . ?
N2 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C10 C9 C8 118.4(11) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C11 C10 C9 118.1(10) . . ?
C11 C10 C7 121.0(11) . . ?
C9 C10 C7 120.8(11) . . ?
C10 C11 C12 120.5(11) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
N2 C12 C11 122.7(10) . . ?
N2 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C12 N2 C8 117.8(9) . . ?
C12 N2 Co1 122.6(7) . 1_455 ?
C8 N2 Co1 119.2(7) . 1_455 ?
C14 C13 C18 120.1(11) . . ?
C14 C13 C18X 118.8(12) . . ?
C14 C13 C19 119.8(8) . . ?
C18 C13 C19 119.7(11) . . ?
C18X C13 C19 119.2(12) . . ?
C15 C14 C13 119.2(8) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16X 121.1(12) . . ?
C14 C15 C16 120.6(11) . . ?
C14 C15 C20 120.0(8) . . ?
C16X C15 C20 118.1(12) . . ?
C16 C15 C20 118.8(10) . . ?
C15 C16 C17 120.9(13) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
N3 C17 C18 120.2(14) . . ?
N3 C17 C16 121.5(14) . . ?
C18 C17 C16 118.3(13) . . ?
C17 N3 H3A 120.0 . . ?
C17 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C17 C18 C13 119.9(14) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C15 C16X C17X 121.4(16) . . ?
C15 C16X H16X 119.3 . . ?
C17X C16X H16X 119.3 . . ?
N3X C17X C18X 122.7(16) . . ?
N3X C17X C16X 120.1(16) . . ?
C18X C17X C16X 116.4(15) . . ?
C17X N3X H3C 120.0 . . ?
C17X N3X H3D 120.0 . . ?
H3C N3X H3D 120.0 . . ?
C17X C18X C13 121.3(16) . . ?
C17X C18X H18X 119.3 . . ?
C13 C18X H18X 119.3 . . ?
O1 C19 O2 120.3(9) . . ?
O1 C19 C13 121.5(9) . . ?
O2 C19 C13 118.2(9) . . ?
C19 O1 Co1 87.2(6) . . ?
C19 O2 Co1 91.9(6) . . ?
O4 C20 O3 123.8(8) . . ?
O4 C20 C15 118.9(8) . . ?
O3 C20 C15 117.4(8) . . ?
C20 O3 Co1 112.9(6) . 2_646 ?
C20 O4 Co1 163.9(7) . 4_566 ?
O5 C21 N4 116(3) . . ?
O5 C21 H21 121.8 . . ?
N4 C21 H21 121.8 . . ?
C21 N4 C22 118(2) . . ?
C21 N4 C23 124(2) . . ?
C22 N4 C23 117(2) . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N4 C23 H23A 109.5 . . ?
N4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O6 C24 N5 119(3) . . ?
O6 C24 H24 120.3 . . ?
N5 C24 H24 120.3 . . ?
C24 N5 C25 116(3) . . ?
C24 N5 C26 127(3) . . ?
C25 N5 C26 116(3) . . ?
N5 C25 H25A 109.5 . . ?
N5 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N5 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N5 C26 H26A 109.5 . . ?
N5 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N5 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O7 C27 N6 118(4) . . ?
O7 C27 H27 121.1 . . ?
N6 C27 H27 121.1 . . ?
C27 N6 C28 116(3) . . ?
C27 N6 C29 124(3) . . ?
C28 N6 C29 119(3) . . ?
N6 C28 H28A 109.5 . . ?
N6 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N6 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N6 C29 H29A 109.5 . . ?
N6 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N6 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 1(2) . . . . ?
Co1 N1 C1 C2 173.5(11) . . . . ?
N1 C1 C2 C3 -1(2) . . . . ?
C1 C2 C3 C4 2(2) . . . . ?
C1 C2 C3 C6 -178.0(13) . . . . ?
C2 C3 C4 C5 -2(2) . . . . ?
C6 C3 C4 C5 177.8(14) . . . . ?
C1 N1 C5 C4 -1(2) . . . . ?
Co1 N1 C5 C4 -174.4(12) . . . . ?
C3 C4 C5 N1 2(2) . . . . ?
C2 C3 C6 C7 177.9(15) . . . . ?
C4 C3 C6 C7 -2(2) . . . . ?
C3 C6 C7 C10 -179.1(13) . . . . ?
N2 C8 C9 C10 0(2) . . . . ?
C8 C9 C10 C11 -1(2) . . . . ?
C8 C9 C10 C7 -178.8(12) . . . . ?
C6 C7 C10 C11 -171.3(14) . . . . ?
C6 C7 C10 C9 7(2) . . . . ?
C9 C10 C11 C12 1(2) . . . . ?
C7 C10 C11 C12 178.7(12) . . . . ?
C10 C11 C12 N2 0(2) . . . . ?
C11 C12 N2 C8 -0.8(19) . . . . ?
C11 C12 N2 Co1 -173.7(10) . . . 1_455 ?
C9 C8 N2 C12 0.6(19) . . . . ?
C9 C8 N2 Co1 173.8(10) . . . 1_455 ?
C18 C13 C14 C15 11(2) . . . . ?
C18X C13 C14 C15 -12(2) . . . . ?
C19 C13 C14 C15 -175.6(11) . . . . ?
C13 C14 C15 C16X 10(3) . . . . ?
C13 C14 C15 C16 -9(2) . . . . ?
C13 C14 C15 C20 179.7(10) . . . . ?
C14 C15 C16 C17 6(3) . . . . ?
C20 C15 C16 C17 176.7(18) . . . . ?
C15 C16 C17 N3 178(2) . . . . ?
C15 C16 C17 C18 -3(4) . . . . ?
N3 C17 C18 C13 -176(2) . . . . ?
C16 C17 C18 C13 5(4) . . . . ?
C14 C13 C18 C17 -9(3) . . . . ?
C19 C13 C18 C17 177.5(18) . . . . ?
C14 C15 C16X C17X -8(4) . . . . ?
C20 C15 C16X C17X -178(2) . . . . ?
C15 C16X C17X N3X 178(3) . . . . ?
C15 C16X C17X C18X 8(5) . . . . ?
N3X C17X C18X C13 179(3) . . . . ?
C16X C17X C18X C13 -11(5) . . . . ?
C14 C13 C18X C17X 14(4) . . . . ?
C19 C13 C18X C17X 177(2) . . . . ?
C14 C13 C19 O1 -179.9(11) . . . . ?
C18 C13 C19 O1 -7(2) . . . . ?
C18X C13 C19 O1 17(3) . . . . ?
C14 C13 C19 O2 -2.9(18) . . . . ?
C18 C13 C19 O2 170.3(17) . . . . ?
C18X C13 C19 O2 -166(2) . . . . ?
O2 C19 O1 Co1 9.8(11) . . . . ?
C13 C19 O1 Co1 -173.4(11) . . . . ?
O1 C19 O2 Co1 -10.3(12) . . . . ?
C13 C19 O2 Co1 172.7(10) . . . . ?
C14 C15 C20 O4 -178.3(10) . . . . ?
C16X C15 C20 O4 -8(2) . . . . ?
C16 C15 C20 O4 11(2) . . . . ?
C14 C15 C20 O3 1.5(14) . . . . ?
C16X C15 C20 O3 172(2) . . . . ?
C16 C15 C20 O3 -169.7(17) . . . . ?
O4 C20 O3 Co1 1.2(12) . . . 2_646 ?
C15 C20 O3 Co1 -178.6(6) . . . 2_646 ?
O3 C20 O4 Co1 97(2) . . . 4_566 ?
C15 C20 O4 Co1 -83(2) . . . 4_566 ?
O5 C21 N4 C22 169(3) . . . . ?
O5 C21 N4 C23 1(4) . . . . ?
O6 C24 N5 C25 172(4) . . . . ?
O6 C24 N5 C26 -5(5) . . . . ?
O7 C27 N6 C28 179(5) . . . . ?
O7 C27 N6 C29 6(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O4 0.95 2.52 3.051(13) 115.2 4_565 yes
C2 H2 O5 0.95 2.63 3.49(2) 150.6 . yes
C5 H5 O3 0.95 2.56 3.057(14) 113.0 2_656 yes
C8 H8 O4 0.95 2.64 3.141(14) 113.2 4_465 yes
C12 H12 O3 0.95 2.64 3.125(14) 112.3 2_556 yes
C16 H16 O2 0.95 2.19 3.134(19) 170.7 4_566 yes
N3 H3A O1 0.88 2.03 2.837(17) 151.1 3_667 yes
N3 H3B O3 0.88 2.64 3.198(15) 122.2 4_566 yes
C16X H16X O2 0.95 2.38 3.22(3) 146.9 4_566 yes
N3X H3C O1 0.88 2.12 2.89(2) 145.7 3_667 yes
C26 H26B N6 0.98 2.59 3.21(9) 121.6 . yes
C29 H29C O5 0.98 2.44 3.35(10) 153.9 4_566 yes

_refine_diff_density_max         2.810
_refine_diff_density_min         -1.069
_refine_diff_density_rms         0.282


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylformamide/ethanol'
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 2207273'
loop_
_audit_author_name
_audit_author_address
'Mark Elsegood'
;Loughborough University
United Kingdom
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT043_akm2                
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..     365.47 Check 
RESPONSE: Accounted for by Squeezed solvent
;
_vrf_PLAT051_akm2                
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      11.43 %     
RESPONSE: Accounted for by Squeezed solvent
;
_vrf_PLAT097_akm2                
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       5.17 eA-3  
RESPONSE: Consequence of unresolved twinning effects.
;
_vrf_PLAT213_akm2                
;
PROBLEM: Atom Mn1             has ADP max/min Ratio .....        6.0 prolat
RESPONSE: Marginal data set with underlying twinning.
;
_vrf_PLAT602_akm2                
;
PROBLEM: Solvent Accessible VOID(S) in Structure ........          ! Check 
RESPONSE: squeezed
;
_vrf_PLAT971_akm2                
;
PROBLEM: Check Calcd Resid. Dens.  1.07Ang From Mn1             4.47 eA-3  
RESPONSE: Marginal data set with underlying twinning.
;
_vrf_PLAT082_akm2                
;
PROBLEM: High R1 Value ..................................       0.17 Report
RESPONSE: Marginal data set with underlying twinning.
;
_vrf_PLAT084_akm2                
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.42 Report
RESPONSE: Marginal data set with underlying twinning.
;
_vrf_PLAT250_akm2                
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.7 Note  
RESPONSE: Marginal data set with underlying twinning.
;
# end Validation Reply Form 

_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 H15 Mn N3 O4, 6(C3 H7 N O)'
_chemical_formula_sum            'C38 H57 Mn N9 O10'
_chemical_formula_weight         854.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 '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                   13.880(6)
_cell_length_b                   17.016(7)
_cell_length_c                   14.142(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.79(4)
_cell_angle_gamma                90
_cell_volume                     3229(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7009
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      28.20

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_F_000             1812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.720
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.480
_exptl_absorpt_coefficient_mu    0.495
_shelx_estimated_absorpt_T_min   0.717
_shelx_estimated_absorpt_T_max   0.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_T_max  0.797
_exptl_absorpt_process_details   'TWINABS v2012/1, Sheldrick, G.M., (2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22679
_diffrn_reflns_av_unetI/netI     0.1937
_diffrn_reflns_av_R_equivalents  0.1170
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.517
_diffrn_reflns_theta_max         28.453
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             7901
_reflns_number_gt                3712
_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 APEX 2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1503P)²+29.8700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7901
_refine_ls_number_parameters     300
_refine_ls_number_restraints     532
_refine_ls_R_factor_all          0.2378
_refine_ls_R_factor_gt           0.1712
_refine_ls_wR_factor_ref         0.4210
_refine_ls_wR_factor_gt          0.3903
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.123
_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
Mn1 Mn 0.01407(11) 0.47848(6) 0.13661(9) 0.0239(4) Uani 1 1 d . U . . .
O1 O 0.0248(5) 0.3674(3) 0.2198(4) 0.0323(13) Uani 1 1 d . U . . .
O2 O 0.0288(6) 0.4732(3) 0.3091(4) 0.0420(16) Uani 1 1 d . U . . .
C1 C 0.0238(9) 0.3994(4) 0.2990(6) 0.0361(16) Uani 1 1 d . U . . .
O3 O -0.0129(5) 0.1063(3) 0.3480(4) 0.0293(12) Uani 1 1 d . U . . .
O4 O -0.0064(5) 0.0877(3) 0.5022(4) 0.0312(13) Uani 1 1 d . U . . .
C2 C -0.0025(7) 0.1318(4) 0.4328(6) 0.0261(15) Uani 1 1 d . U . . .
C3 C 0.0118(9) 0.3476(4) 0.3812(6) 0.0376(17) Uani 1 1 d . U . . .
C4 C 0.0085(8) 0.2682(4) 0.3705(6) 0.0346(18) Uani 1 1 d . U . . .
H4 H 0.010032 0.245490 0.309508 0.041 Uiso 1 1 calc R U . . .
C5 C 0.0030(8) 0.2203(4) 0.4481(6) 0.0310(16) Uani 1 1 d . U . . .
C6 C 0.0014(9) 0.2513(4) 0.5397(6) 0.043(2) Uani 1 1 d . U . . .
H6 H -0.003037 0.217403 0.591735 0.052 Uiso 1 1 calc R U . . .
C7 C 0.0066(11) 0.3347(5) 0.5538(7) 0.057(2) Uani 1 1 d . U . . .
C8 C 0.0157(10) 0.3809(5) 0.4741(7) 0.053(2) Uani 1 1 d . U . . .
H8 H 0.024632 0.436070 0.482744 0.063 Uiso 1 1 calc R U . . .
N1 N 0.0120(12) 0.3666(4) 0.6416(6) 0.093(4) Uani 1 1 d . U . . .
H1A H 0.021329 0.417493 0.650255 0.111 Uiso 1 1 calc R U . . .
H1B H 0.006154 0.336639 0.690546 0.111 Uiso 1 1 calc R U . . .
N2 N 0.1788(6) 0.4873(4) 0.1503(6) 0.0316(12) Uani 1 1 d . U . . .
C9 C 0.2297(7) 0.4289(5) 0.1170(8) 0.0396(17) Uani 1 1 d . U . . .
H9 H 0.194165 0.382089 0.093735 0.048 Uiso 1 1 calc R U . . .
C10 C 0.3187(7) 0.4321(6) 0.1149(8) 0.0446(19) Uani 1 1 d . U . . .
H10 H 0.345567 0.391406 0.083378 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3801(8) 0.4948(6) 0.1581(9) 0.0434(18) Uani 1 1 d . U . . .
C12 C 0.3277(8) 0.5525(6) 0.2019(9) 0.047(2) Uani 1 1 d . U . . .
H12 H 0.363032 0.596230 0.235559 0.056 Uiso 1 1 calc R U . . .
C13 C 0.2370(7) 0.5453(6) 0.1959(8) 0.0392(17) Uani 1 1 d . U . . .
H13 H 0.206758 0.584548 0.226424 0.047 Uiso 1 1 calc R U . . .
C14 C 0.4859(7) 0.5020(5) 0.1641(8) 0.0404(19) Uani 1 1 d . U . . .
H14 H 0.521652 0.539856 0.208901 0.061 Uiso 1 1 calc R U . . .
C15 C 0.5416(8) 0.4588(5) 0.1104(8) 0.0415(17) Uani 1 1 d . U . . .
H15 H 0.505484 0.421577 0.064826 0.062 Uiso 1 1 calc R U . . .
C16 C 0.6468(8) 0.4649(6) 0.1171(9) 0.0451(18) Uani 1 1 d . U . . .
C17 C 0.7059(9) 0.5270(7) 0.1652(9) 0.053(2) Uani 1 1 d . U . . .
H17 H 0.677666 0.566349 0.197427 0.063 Uiso 1 1 calc R U . . .
C18 C 0.8079(8) 0.5306(5) 0.1654(9) 0.0448(19) Uani 1 1 d . U . . .
H18 H 0.848557 0.571761 0.199618 0.054 Uiso 1 1 calc R U . . .
N3 N 0.8487(6) 0.4747(4) 0.1162(6) 0.0323(14) Uani 1 1 d . U . . .
C19 C 0.7882(8) 0.4208(6) 0.0689(8) 0.0399(18) Uani 1 1 d . U . . .
H19 H 0.816153 0.382364 0.034987 0.048 Uiso 1 1 calc R U . . .
C20 C 0.6891(8) 0.4142(6) 0.0632(8) 0.0453(19) Uani 1 1 d . U . . .
H20 H 0.649845 0.375269 0.022891 0.054 Uiso 1 1 calc R U . . .
O5 O 0.4668(11) 0.3011(7) -0.0249(11) 0.120(4) Uani 1 1 d . U . . .
C21 C 0.4268(15) 0.2809(12) -0.0994(18) 0.122(4) Uani 1 1 d D U . . .
H21 H 0.464439 0.275074 -0.146432 0.146 Uiso 1 1 calc R U . . .
N4 N 0.3187(13) 0.2622(9) -0.1306(13) 0.113(4) Uani 1 1 d D U . . .
C22 C 0.2489(16) 0.2461(10) -0.2248(15) 0.115(5) Uani 1 1 d . U . . .
H22A H 0.219101 0.194091 -0.223223 0.173 Uiso 1 1 calc R U . . .
H22B H 0.284467 0.247405 -0.276437 0.173 Uiso 1 1 calc R U . . .
H22C H 0.196339 0.286092 -0.238146 0.173 Uiso 1 1 calc R U . . .
C23 C 0.2599(16) 0.2587(12) -0.0497(16) 0.120(5) Uani 1 1 d . U . . .
H23A H 0.208954 0.299962 -0.061763 0.180 Uiso 1 1 calc R U . . .
H23B H 0.306147 0.266836 0.014648 0.180 Uiso 1 1 calc R U . . .
H23C H 0.227929 0.207231 -0.051346 0.180 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 O4 2.164(6) 4_565 ?
Mn1 O3 2.186(5) 2 ?
Mn1 O1 2.211(5) . ?
Mn1 N3 2.240(8) 1_455 ?
Mn1 N2 2.250(8) . ?
Mn1 O2 2.397(6) . ?
Mn1 C1 2.635(8) . ?
O1 C1 1.248(10) . ?
O2 C1 1.264(9) . ?
C1 C3 1.502(11) . ?
O3 C2 1.249(10) . ?
O4 C2 1.248(9) . ?
C2 C5 1.521(10) . ?
C3 C4 1.358(10) . ?
C3 C8 1.420(12) . ?
C4 C5 1.386(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(11) . ?
C6 C7 1.431(11) . ?
C6 H6 0.9500 . ?
C7 N1 1.339(12) . ?
C7 C8 1.406(12) . ?
C8 H8 0.9500 . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C13 1.333(12) . ?
N2 C9 1.371(11) . ?
C9 C10 1.244(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.404(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.451(14) . ?
C11 C14 1.454(15) . ?
C12 C13 1.246(14) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.420(13) . ?
C14 H14 0.9500 . ?
C15 C16 1.443(15) . ?
C15 H15 0.9500 . ?
C16 C20 1.378(14) . ?
C16 C17 1.402(15) . ?
C17 C18 1.416(15) . ?
C17 H17 0.9500 . ?
C18 N3 1.382(11) . ?
C18 H18 0.9500 . ?
N3 C19 1.308(12) . ?
C19 C20 1.362(15) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
O5 C21 1.11(2) . ?
C21 N4 1.486(16) . ?
C21 H21 0.9500 . ?
N4 C22 1.46(2) . ?
N4 C23 1.57(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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 Mn1 O3 127.0(2) 4_565 2 ?
O4 Mn1 O1 89.9(2) 4_565 . ?
O3 Mn1 O1 143.0(2) 2 . ?
O4 Mn1 N3 88.4(3) 4_565 1_455 ?
O3 Mn1 N3 90.5(2) 2 1_455 ?
O1 Mn1 N3 88.4(3) . 1_455 ?
O4 Mn1 N2 90.7(3) 4_565 . ?
O3 Mn1 N2 87.6(3) 2 . ?
O1 Mn1 N2 94.7(3) . . ?
N3 Mn1 N2 176.8(3) 1_455 . ?
O4 Mn1 O2 146.3(2) 4_565 . ?
O3 Mn1 O2 86.38(19) 2 . ?
O1 Mn1 O2 56.62(19) . . ?
N3 Mn1 O2 87.0(3) 1_455 . ?
N2 Mn1 O2 95.4(3) . . ?
O4 Mn1 C1 117.7(2) 4_565 . ?
O3 Mn1 C1 114.9(2) 2 . ?
O1 Mn1 C1 28.2(2) . . ?
N3 Mn1 C1 85.4(3) 1_455 . ?
N2 Mn1 C1 97.7(3) . . ?
O2 Mn1 C1 28.6(2) . . ?
C1 O1 Mn1 95.1(4) . . ?
C1 O2 Mn1 86.2(5) . . ?
O1 C1 O2 121.5(7) . . ?
O1 C1 C3 117.8(7) . . ?
O2 C1 C3 120.6(7) . . ?
O1 C1 Mn1 56.7(4) . . ?
O2 C1 Mn1 65.2(4) . . ?
C3 C1 Mn1 169.5(8) . . ?
C2 O3 Mn1 104.6(4) . 2_545 ?
C2 O4 Mn1 168.9(6) . 4_566 ?
O4 C2 O3 121.9(7) . . ?
O4 C2 C5 119.6(7) . . ?
O3 C2 C5 118.0(6) . . ?
C4 C3 C8 119.5(7) . . ?
C4 C3 C1 120.3(7) . . ?
C8 C3 C1 119.7(7) . . ?
C3 C4 C5 120.2(8) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 121.8(7) . . ?
C4 C5 C2 118.8(7) . . ?
C6 C5 C2 119.5(7) . . ?
C5 C6 C7 119.3(7) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
N1 C7 C8 121.3(8) . . ?
N1 C7 C6 121.3(8) . . ?
C8 C7 C6 117.0(8) . . ?
C7 C8 C3 121.8(8) . . ?
C7 C8 H8 119.1 . . ?
C3 C8 H8 119.1 . . ?
C7 N1 H1A 120.0 . . ?
C7 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C13 N2 C9 113.6(8) . . ?
C13 N2 Mn1 124.6(6) . . ?
C9 N2 Mn1 121.6(6) . . ?
C10 C9 N2 125.3(9) . . ?
C10 C9 H9 117.3 . . ?
N2 C9 H9 117.3 . . ?
C9 C10 C11 121.3(10) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 112.6(10) . . ?
C10 C11 C14 125.6(9) . . ?
C12 C11 C14 121.8(9) . . ?
C13 C12 C11 120.8(10) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 N2 125.7(9) . . ?
C12 C13 H13 117.2 . . ?
N2 C13 H13 117.2 . . ?
C15 C14 C11 127.2(9) . . ?
C15 C14 H14 116.4 . . ?
C11 C14 H14 116.4 . . ?
C14 C15 C16 127.4(9) . . ?
C14 C15 H15 116.3 . . ?
C16 C15 H15 116.3 . . ?
C20 C16 C17 117.4(10) . . ?
C20 C16 C15 119.0(10) . . ?
C17 C16 C15 122.9(9) . . ?
C16 C17 C18 119.7(10) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
N3 C18 C17 120.4(9) . . ?
N3 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C19 N3 C18 116.7(9) . . ?
C19 N3 Mn1 126.1(6) . 1_655 ?
C18 N3 Mn1 117.0(6) . 1_655 ?
N3 C19 C20 126.5(9) . . ?
N3 C19 H19 116.8 . . ?
C20 C19 H19 116.8 . . ?
C19 C20 C16 118.9(10) . . ?
C19 C20 H20 120.6 . . ?
C16 C20 H20 120.6 . . ?
O5 C21 N4 125(2) . . ?
O5 C21 H21 117.7 . . ?
N4 C21 H21 117.7 . . ?
C22 N4 C21 134.0(19) . . ?
C22 N4 C23 108.2(17) . . ?
C21 N4 C23 117.8(17) . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N4 C23 H23A 109.5 . . ?
N4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O1 C1 O2 -7.7(12) . . . . ?
Mn1 O1 C1 C3 169.5(9) . . . . ?
Mn1 O2 C1 O1 7.1(11) . . . . ?
Mn1 O2 C1 C3 -170.1(10) . . . . ?
Mn1 O4 C2 O3 128(3) 4_566 . . . ?
Mn1 O4 C2 C5 -59(3) 4_566 . . . ?
Mn1 O3 C2 O4 -8.2(11) 2_545 . . . ?
Mn1 O3 C2 C5 179.0(7) 2_545 . . . ?
O1 C1 C3 C4 4.1(17) . . . . ?
O2 C1 C3 C4 -178.6(11) . . . . ?
Mn1 C1 C3 C4 60(4) . . . . ?
O1 C1 C3 C8 176.6(11) . . . . ?
O2 C1 C3 C8 -6.1(17) . . . . ?
Mn1 C1 C3 C8 -127(3) . . . . ?
C8 C3 C4 C5 3.8(18) . . . . ?
C1 C3 C4 C5 176.4(10) . . . . ?
C3 C4 C5 C6 -0.5(17) . . . . ?
C3 C4 C5 C2 178.9(10) . . . . ?
O4 C2 C5 C4 179.2(10) . . . . ?
O3 C2 C5 C4 -7.8(14) . . . . ?
O4 C2 C5 C6 -1.3(15) . . . . ?
O3 C2 C5 C6 171.6(10) . . . . ?
C4 C5 C6 C7 -0.6(18) . . . . ?
C2 C5 C6 C7 180.0(11) . . . . ?
C5 C6 C7 N1 -175.5(13) . . . . ?
C5 C6 C7 C8 -2(2) . . . . ?
N1 C7 C8 C3 178.9(14) . . . . ?
C6 C7 C8 C3 5(2) . . . . ?
C4 C3 C8 C7 -6(2) . . . . ?
C1 C3 C8 C7 -178.8(12) . . . . ?
C13 N2 C9 C10 -10.2(15) . . . . ?
Mn1 N2 C9 C10 174.0(9) . . . . ?
N2 C9 C10 C11 7.5(18) . . . . ?
C9 C10 C11 C12 -0.8(17) . . . . ?
C9 C10 C11 C14 176.6(11) . . . . ?
C10 C11 C12 C13 -2.6(17) . . . . ?
C14 C11 C12 C13 179.9(11) . . . . ?
C11 C12 C13 N2 -0.5(19) . . . . ?
C9 N2 C13 C12 6.4(16) . . . . ?
Mn1 N2 C13 C12 -177.8(9) . . . . ?
C10 C11 C14 C15 15.4(19) . . . . ?
C12 C11 C14 C15 -167.5(11) . . . . ?
C11 C14 C15 C16 -179.0(11) . . . . ?
C14 C15 C16 C20 175.8(11) . . . . ?
C14 C15 C16 C17 -13.3(19) . . . . ?
C20 C16 C17 C18 -6.5(18) . . . . ?
C15 C16 C17 C18 -177.5(11) . . . . ?
C16 C17 C18 N3 1.9(18) . . . . ?
C17 C18 N3 C19 1.5(15) . . . . ?
C17 C18 N3 Mn1 -173.0(8) . . . 1_655 ?
C18 N3 C19 C20 0.0(16) . . . . ?
Mn1 N3 C19 C20 173.8(9) 1_655 . . . ?
N3 C19 C20 C16 -4.8(18) . . . . ?
C17 C16 C20 C19 7.8(17) . . . . ?
C15 C16 C20 C19 179.2(10) . . . . ?
O5 C21 N4 C22 170(2) . . . . ?
O5 C21 N4 C23 -9(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 H1A O2 0.88 2.12 2.906(10) 148.9 3_566 yes
N1 H1B O3 0.88 2.50 3.061(10) 121.8 4_566 yes
C15 H15 O5 0.95 2.40 3.304(16) 159.5 . yes

_refine_diff_density_max         5.171
_refine_diff_density_min         -1.431
_refine_diff_density_rms         0.245


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylformamide/methanol'
####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 2207274'
loop_
_audit_author_name
_audit_author_address
'Mark Elsegood'
;Loughborough University
United Kingdom
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2022-12-06 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         'C18 H13 Mn N5 O4, 2.5(C3 H7 N O)'
_chemical_formula_sum            'C25.50 H30.50 Mn N7.50 O6.50'
_chemical_formula_weight         601.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 '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                   13.583(6)
_cell_length_b                   16.964(8)
_cell_length_c                   14.247(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.880(5)
_cell_angle_gamma                90
_cell_volume                     3106(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5380
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      25.37

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             1252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.475
_shelx_estimated_absorpt_T_min   0.741
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_process_details   'SADABS v2012/1, Sheldrick, G.M., (2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
'Bruker APEX 2 CCD area detector diffractometer'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22188
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.584
_diffrn_reflns_theta_max         25.554
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5731
_reflns_number_gt                3579
_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. 
;

_computing_data_collection       'Bruker APEX 2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1694P)²+6.8148P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         5731
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1391
_refine_ls_R_factor_gt           0.0967
_refine_ls_wR_factor_ref         0.3081
_refine_ls_wR_factor_gt          0.2714
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
Mn1 Mn -0.01863(7) 0.52147(5) 0.35910(7) 0.0376(3) Uani 1 1 d . . . . .
N1 N 0.1577(4) 0.5288(3) 0.3846(4) 0.0484(13) Uani 1 1 d . . . . .
C1 C 0.2119(6) 0.4670(4) 0.3722(7) 0.063(2) Uani 1 1 d . . . . .
H1 H 0.1797 0.4167 0.3644 0.076 Uiso 1 1 calc R U . . .
C2 C 0.3121(7) 0.4718(5) 0.3699(8) 0.082(3) Uani 1 1 d . . . . .
H2 H 0.3466 0.4261 0.3575 0.098 Uiso 1 1 calc R U . . .
C3 C 0.3620(6) 0.5440(5) 0.3860(8) 0.073(2) Uani 1 1 d . . . . .
C4 C 0.3059(7) 0.6108(6) 0.3997(10) 0.111(4) Uani 1 1 d . . . . .
H4 H 0.3367 0.6617 0.4093 0.134 Uiso 1 1 calc R U . . .
C5 C 0.2059(7) 0.5998(5) 0.3988(8) 0.088(3) Uani 1 1 d . . . . .
H5 H 0.1682 0.6444 0.4087 0.105 Uiso 1 1 calc R U . . .
N2 N 0.4673(5) 0.5582(4) 0.3844(7) 0.083(2) Uani 1 1 d . . . . .
N3 N 0.5043(6) 0.4994(5) 0.3562(8) 0.104(3) Uani 1 1 d . . . . .
N4 N 0.8101(4) 0.5159(3) 0.3455(4) 0.0479(13) Uani 1 1 d . . . . .
C6 C 0.7555(7) 0.4474(5) 0.3320(9) 0.094(4) Uani 1 1 d . . . . .
H6 H 0.7885 0.4008 0.3205 0.113 Uiso 1 1 calc R U . . .
C7 C 0.6545(7) 0.4416(5) 0.3339(11) 0.110(4) Uani 1 1 d . . . . .
H7 H 0.6194 0.3923 0.3240 0.132 Uiso 1 1 calc R U . . .
C8 C 0.6058(6) 0.5099(5) 0.3507(8) 0.076(3) Uani 1 1 d . . . . .
C9 C 0.6603(6) 0.5802(5) 0.3663(8) 0.077(3) Uani 1 1 d . . . . .
H9 H 0.6302 0.6273 0.3808 0.092 Uiso 1 1 calc R U . . .
C10 C 0.7599(6) 0.5799(4) 0.3602(7) 0.065(2) Uani 1 1 d . . . . .
H10 H 0.7951 0.6290 0.3669 0.078 Uiso 1 1 calc R U . . .
N5 N -0.0501(6) 0.8694(3) 0.3428(4) 0.0638(18) Uani 1 1 d . . . . .
C11 C -0.0368(6) 0.8362(4) 0.4355(5) 0.0486(16) Uani 1 1 d . . . . .
C12 C -0.0231(5) 0.7547(3) 0.4513(5) 0.0424(15) Uani 1 1 d . . . . .
H12 H -0.0199 0.7217 0.3986 0.051 Uiso 1 1 calc R U . . .
C13 C -0.0140(4) 0.7208(3) 0.5453(4) 0.0334(12) Uani 1 1 d . . . . .
C14 C -0.0192(5) 0.7696(3) 0.6231(4) 0.0377(14) Uani 1 1 d . . . . .
H14 H -0.0126 0.7475 0.6861 0.045 Uiso 1 1 calc R U . . .
C15 C -0.0341(5) 0.8503(3) 0.6078(5) 0.0394(14) Uani 1 1 d . . . . .
C16 C -0.0416(6) 0.8835(3) 0.5162(5) 0.0476(17) Uani 1 1 d . . . . .
H16 H -0.0502 0.9389 0.5075 0.057 Uiso 1 1 calc R U . . .
C17 C 0.0003(5) 0.6335(3) 0.5600(5) 0.0401(14) Uani 1 1 d . . . . .
O1 O 0.0072(4) 0.5901(2) 0.4913(3) 0.0477(11) Uani 1 1 d . . . . .
O2 O 0.0077(3) 0.6056(2) 0.6454(3) 0.0392(10) Uani 1 1 d . . . . .
C18 C -0.0364(5) 0.9015(3) 0.6939(5) 0.0424(15) Uani 1 1 d . . . . .
O3 O -0.0412(4) 0.8688(2) 0.7719(3) 0.0474(11) Uani 1 1 d . . . . .
O4 O -0.0381(4) 0.9766(2) 0.6850(3) 0.0507(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 2.145(4) . ?
Mn1 O2 2.163(4) 3_566 ?
Mn1 O3 2.204(4) 4_575 ?
Mn1 N4 2.273(5) 1_455 ?
Mn1 N1 2.306(6) . ?
Mn1 O4 2.408(5) 4_575 ?
Mn1 C18 2.634(6) 4_575 ?
N1 C1 1.325(8) . ?
N1 C5 1.355(9) . ?
C1 C2 1.375(11) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.415(12) . ?
C3 N2 1.457(10) . ?
C4 C5 1.366(11) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
N2 N3 1.241(10) . ?
N3 C8 1.416(9) . ?
N4 C10 1.335(8) . ?
N4 C6 1.358(9) . ?
N4 Mn1 2.273(5) 1_655 ?
C6 C7 1.384(11) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(12) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(10) . ?
C9 C10 1.383(10) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
N5 C11 1.393(8) . ?
C11 C12 1.403(8) . ?
C11 C16 1.420(9) . ?
C12 C13 1.426(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.403(8) . ?
C13 C17 1.499(8) . ?
C14 C15 1.392(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(8) . ?
C15 C18 1.512(8) . ?
C16 H16 0.9500 . ?
C17 O1 1.253(7) . ?
C17 O2 1.279(7) . ?
O2 Mn1 2.163(4) 3_566 ?
C18 O3 1.262(7) . ?
C18 O4 1.280(7) . ?
C18 Mn1 2.634(6) 4_576 ?
O3 Mn1 2.204(4) 4_576 ?
O4 Mn1 2.408(5) 4_576 ?

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 Mn1 O2 125.00(15) . 3_566 ?
O1 Mn1 O3 89.46(15) . 4_575 ?
O2 Mn1 O3 145.41(15) 3_566 4_575 ?
O1 Mn1 N4 88.25(19) . 1_455 ?
O2 Mn1 N4 91.94(17) 3_566 1_455 ?
O3 Mn1 N4 92.02(18) 4_575 1_455 ?
O1 Mn1 N1 88.06(19) . . ?
O2 Mn1 N1 88.89(17) 3_566 . ?
O3 Mn1 N1 89.51(19) 4_575 . ?
N4 Mn1 N1 176.0(2) 1_455 . ?
O1 Mn1 O4 146.09(14) . 4_575 ?
O2 Mn1 O4 88.19(13) 3_566 4_575 ?
O3 Mn1 O4 57.25(13) 4_575 4_575 ?
N4 Mn1 O4 98.31(19) 1_455 4_575 ?
N1 Mn1 O4 85.63(19) . 4_575 ?
O1 Mn1 C18 117.24(17) . 4_575 ?
O2 Mn1 C18 117.06(17) 3_566 4_575 ?
O3 Mn1 C18 28.52(16) 4_575 4_575 ?
N4 Mn1 C18 98.6(2) 1_455 4_575 ?
N1 Mn1 C18 84.5(2) . 4_575 ?
O4 Mn1 C18 28.97(15) 4_575 4_575 ?
C1 N1 C5 117.4(6) . . ?
C1 N1 Mn1 122.0(4) . . ?
C5 N1 Mn1 119.9(5) . . ?
N1 C1 C2 123.7(7) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 118.9(7) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 118.4(7) . . ?
C2 C3 N2 125.0(7) . . ?
C4 C3 N2 116.5(7) . . ?
C5 C4 C3 117.9(8) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
N1 C5 C4 123.6(8) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
N3 N2 C3 112.1(7) . . ?
N2 N3 C8 115.0(7) . . ?
C10 N4 C6 115.8(6) . . ?
C10 N4 Mn1 120.9(5) . 1_655 ?
C6 N4 Mn1 123.0(5) . 1_655 ?
N4 C6 C7 123.9(7) . . ?
N4 C6 H6 118.0 . . ?
C7 C6 H6 118.0 . . ?
C6 C7 C8 118.2(7) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C9 C8 C7 119.1(7) . . ?
C9 C8 N3 125.3(7) . . ?
C7 C8 N3 115.5(7) . . ?
C10 C9 C8 118.0(7) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
N4 C10 C9 124.9(7) . . ?
N4 C10 H10 117.5 . . ?
C9 C10 H10 117.5 . . ?
N5 C11 C12 121.3(5) . . ?
N5 C11 C16 120.9(5) . . ?
C12 C11 C16 117.7(5) . . ?
C11 C12 C13 121.0(5) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 119.5(5) . . ?
C14 C13 C17 120.6(5) . . ?
C12 C13 C17 119.9(5) . . ?
C15 C14 C13 119.9(5) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.5(5) . . ?
C14 C15 C18 118.6(5) . . ?
C16 C15 C18 120.9(5) . . ?
C15 C16 C11 121.4(5) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
O1 C17 O2 121.5(5) . . ?
O1 C17 C13 120.8(5) . . ?
O2 C17 C13 117.7(5) . . ?
C17 O1 Mn1 166.7(5) . . ?
C17 O2 Mn1 109.0(4) . 3_566 ?
O3 C18 O4 121.4(5) . . ?
O3 C18 C15 118.8(5) . . ?
O4 C18 C15 119.7(5) . . ?
O3 C18 Mn1 56.5(3) . 4_576 ?
O4 C18 Mn1 65.7(3) . 4_576 ?
C15 C18 Mn1 172.0(5) . 4_576 ?
C18 O3 Mn1 95.0(3) . 4_576 ?
C18 O4 Mn1 85.4(4) . 4_576 ?

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
C5 N1 C1 C2 -2.1(14) . . . . ?
Mn1 N1 C1 C2 168.4(8) . . . . ?
N1 C1 C2 C3 3.1(15) . . . . ?
C1 C2 C3 C4 -2.8(16) . . . . ?
C1 C2 C3 N2 -179.1(9) . . . . ?
C2 C3 C4 C5 1.6(18) . . . . ?
N2 C3 C4 C5 178.3(10) . . . . ?
C1 N1 C5 C4 0.8(16) . . . . ?
Mn1 N1 C5 C4 -169.9(10) . . . . ?
C3 C4 C5 N1 -0.6(19) . . . . ?
C2 C3 N2 N3 7.4(15) . . . . ?
C4 C3 N2 N3 -169.0(11) . . . . ?
C3 N2 N3 C8 178.5(9) . . . . ?
C10 N4 C6 C7 -0.8(16) . . . . ?
Mn1 N4 C6 C7 173.0(10) 1_655 . . . ?
N4 C6 C7 C8 0(2) . . . . ?
C6 C7 C8 C9 -1.0(19) . . . . ?
C6 C7 C8 N3 -177.3(11) . . . . ?
N2 N3 C8 C9 -5.4(17) . . . . ?
N2 N3 C8 C7 170.6(11) . . . . ?
C7 C8 C9 C10 2.8(16) . . . . ?
N3 C8 C9 C10 178.7(10) . . . . ?
C6 N4 C10 C9 2.8(13) . . . . ?
Mn1 N4 C10 C9 -171.1(7) 1_655 . . . ?
C8 C9 C10 N4 -3.8(15) . . . . ?
N5 C11 C12 C13 -177.3(7) . . . . ?
C16 C11 C12 C13 -0.3(10) . . . . ?
C11 C12 C13 C14 0.3(10) . . . . ?
C11 C12 C13 C17 179.9(6) . . . . ?
C12 C13 C14 C15 0.5(9) . . . . ?
C17 C13 C14 C15 -179.1(6) . . . . ?
C13 C14 C15 C16 -1.4(10) . . . . ?
C13 C14 C15 C18 -178.3(6) . . . . ?
C14 C15 C16 C11 1.4(11) . . . . ?
C18 C15 C16 C11 178.3(6) . . . . ?
N5 C11 C16 C15 176.5(7) . . . . ?
C12 C11 C16 C15 -0.6(11) . . . . ?
C14 C13 C17 O1 -178.5(6) . . . . ?
C12 C13 C17 O1 1.9(9) . . . . ?
C14 C13 C17 O2 -0.1(9) . . . . ?
C12 C13 C17 O2 -179.7(6) . . . . ?
O2 C17 O1 Mn1 110.0(16) . . . . ?
C13 C17 O1 Mn1 -71.7(19) . . . . ?
O1 C17 O2 Mn1 -4.9(7) . . . 3_566 ?
C13 C17 O2 Mn1 176.7(4) . . . 3_566 ?
C14 C15 C18 O3 -11.0(9) . . . . ?
C16 C15 C18 O3 172.1(6) . . . . ?
C14 C15 C18 O4 172.1(6) . . . . ?
C16 C15 C18 O4 -4.8(10) . . . . ?
O4 C18 O3 Mn1 -10.7(7) . . . 4_576 ?
C15 C18 O3 Mn1 172.4(5) . . . 4_576 ?
O3 C18 O4 Mn1 9.8(6) . . . 4_576 ?
C15 C18 O4 Mn1 -173.4(6) . . . 4_576 ?

_refine_diff_density_max         1.754
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.122



####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2207269'
loop_
_audit_author_name
_audit_author_address
'Mark Elsegood'
;Loughborough University
United Kingdom
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2022-12-06 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         'C28 H21 Co2 N7 O10, 2(C2 H6 O)'
_chemical_formula_sum            'C32 H33 Co2 N7 O12'
_chemical_formula_weight         825.51

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

_space_group_crystal_system      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                   20.5321(19)
_cell_length_b                   9.8581(9)
_cell_length_c                   18.1007(17)
_cell_angle_alpha                90
_cell_angle_beta                 109.2702(13)
_cell_angle_gamma                90
_cell_volume                     3458.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4627
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.87

_exptl_crystal_description       lath
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.034
_shelx_estimated_absorpt_T_min   0.610
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.610
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_process_details   'SADABS v2009/1, Sheldrick, G.M., (2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16932
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.102
_diffrn_reflns_theta_max         28.174
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4235
_reflns_number_gt                3213
_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 APEX 2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_refine_special_details          
; 
2012-07-13 # Formatted by publCIF 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1025P)²+2.8310P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4235
_refine_ls_number_parameters     319
_refine_ls_number_restraints     510
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1444
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      0.997
_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 0.53372(2) 0.33941(4) 0.06413(2) 0.03084(16) Uani 1 1 d . . . . .
O1 O 0.50599(12) 0.3022(3) -0.05093(13) 0.0453(6) Uani 1 1 d . . . . .
O2 O 0.49429(12) 0.5001(2) -0.11491(15) 0.0473(6) Uani 1 1 d . . . . .
C1 C 0.50062(14) 0.3724(3) -0.11033(18) 0.0372(7) Uani 1 1 d . . . . .
N1 N 0.500000 -0.0540(5) -0.250000 0.0693(16) Uani 1 2 d S T P . .
H1 H 0.485(3) -0.107(5) -0.221(3) 0.083 Uiso 1 1 d . U . . .
C2 C 0.500000 0.0864(5) -0.250000 0.0444(10) Uani 1 2 d S T P . .
C3 C 0.50110(18) 0.1589(3) -0.18354(19) 0.0400(7) Uani 1 1 d . . . . .
H3 H 0.502189 0.111182 -0.137555 0.048 Uiso 1 1 calc R U . . .
C4 C 0.50065(14) 0.2993(3) -0.18332(17) 0.0340(6) Uani 1 1 d . . . . .
C5 C 0.500000 0.3713(4) -0.250000 0.0322(8) Uani 1 2 d S T P . .
H5 H 0.500000 0.467677 -0.250000 0.039 Uiso 1 2 calc R U P . .
N2 N 0.62726(12) 0.4352(3) 0.06213(15) 0.0383(6) Uani 1 1 d D U . . .
C6 C 0.6650(5) 0.3824(11) 0.0218(6) 0.037(2) Uani 0.621(16) 1 d D U P A 1
H6 H 0.648995 0.301899 -0.007413 0.045 Uiso 0.621(16) 1 calc R U P A 1
C7 C 0.7257(6) 0.4385(12) 0.0204(7) 0.045(3) Uani 0.621(16) 1 d D U P A 1
H7 H 0.750168 0.397123 -0.009990 0.054 Uiso 0.621(16) 1 calc R U P A 1
C8 C 0.75175(14) 0.5546(3) 0.06261(18) 0.0376(7) Uani 1 1 d D U . . .
C9 C 0.7096(3) 0.6206(8) 0.0971(5) 0.0390(16) Uani 0.621(16) 1 d D U P A 1
H9 H 0.722420 0.706164 0.121830 0.047 Uiso 0.621(16) 1 calc R U P A 1
C10 C 0.6491(3) 0.5598(8) 0.0947(5) 0.0391(16) Uani 0.621(16) 1 d D U P A 1
H10 H 0.619999 0.607211 0.117269 0.047 Uiso 0.621(16) 1 calc R U P A 1
C6X C 0.6547(8) 0.4099(18) 0.0060(9) 0.038(4) Uani 0.379(16) 1 d D U P A 2
H6X H 0.630087 0.352766 -0.036253 0.046 Uiso 0.379(16) 1 calc R U P A 2
C7X C 0.7167(9) 0.463(2) 0.0065(11) 0.041(4) Uani 0.379(16) 1 d D U P A 2
H7X H 0.735626 0.435284 -0.032466 0.049 Uiso 0.379(16) 1 calc R U P A 2
C9X C 0.7274(6) 0.5653(16) 0.1284(8) 0.046(3) Uani 0.379(16) 1 d D U P A 2
H9X H 0.753139 0.614054 0.173971 0.056 Uiso 0.379(16) 1 calc R U P A 2
C10X C 0.6654(6) 0.5029(17) 0.1240(7) 0.047(3) Uani 0.379(16) 1 d D U P A 2
H10X H 0.649904 0.509399 0.167856 0.056 Uiso 0.379(16) 1 calc R U P A 2
N3 N 0.94132(12) 0.7414(3) 0.06514(14) 0.0331(5) Uani 1 1 d D U . . .
C11 C 0.9181(4) 0.6292(8) 0.0240(5) 0.0334(15) Uani 0.621(16) 1 d D U P A 1
H11 H 0.944221 0.592366 -0.005866 0.040 Uiso 0.621(16) 1 calc R U P A 1
C12 C 0.8584(4) 0.5631(9) 0.0223(5) 0.0366(17) Uani 0.621(16) 1 d D U P A 1
H12 H 0.845102 0.481219 -0.006428 0.044 Uiso 0.621(16) 1 calc R U P A 1
C13 C 0.81739(14) 0.6185(3) 0.06347(18) 0.0351(6) Uani 1 1 d D U . . .
C14 C 0.8438(6) 0.7310(12) 0.1099(6) 0.034(2) Uani 0.621(16) 1 d D U P A 1
H14 H 0.819597 0.768686 0.141595 0.040 Uiso 0.621(16) 1 calc R U P A 1
C15 C 0.9052(5) 0.7882(12) 0.1099(6) 0.033(2) Uani 0.621(16) 1 d D U P A 1
H15 H 0.922712 0.863924 0.142992 0.040 Uiso 0.621(16) 1 calc R U P A 1
C11X C 0.9050(7) 0.6587(15) 0.0056(9) 0.048(4) Uani 0.379(16) 1 d D U P A 2
H11X H 0.922863 0.643418 -0.035873 0.058 Uiso 0.379(16) 1 calc R U P A 2
C12X C 0.8441(8) 0.5959(17) 0.0016(9) 0.047(4) Uani 0.379(16) 1 d D U P A 2
H12X H 0.820683 0.538991 -0.041292 0.057 Uiso 0.379(16) 1 calc R U P A 2
C14X C 0.8528(9) 0.704(2) 0.1225(11) 0.037(4) Uani 0.379(16) 1 d D U P A 2
H14X H 0.835194 0.725991 0.163398 0.044 Uiso 0.379(16) 1 calc R U P A 2
C15X C 0.9144(10) 0.759(2) 0.1218(11) 0.043(5) Uani 0.379(16) 1 d D U P A 2
H15X H 0.939522 0.812995 0.165248 0.052 Uiso 0.379(16) 1 calc R U P A 2
O3 O 0.58942(14) 0.1441(3) 0.0879(2) 0.0622(7) Uani 1 1 d . . . . .
O4 O 0.59017(14) 0.2691(4) 0.18416(16) 0.0628(8) Uani 1 1 d . . . . .
N4 N 0.61116(17) 0.1633(4) 0.1614(2) 0.0675(11) Uani 1 1 d . . . . .
O5 O 0.64989(19) 0.0809(5) 0.2058(3) 0.1121(16) Uani 1 1 d . . . . .
O6 O 0.7587(3) -0.0055(8) 0.1545(4) 0.156(3) Uani 1 1 d . . . . .
H6A H 0.724438 0.041125 0.154521 0.234 Uiso 1 1 calc R U . . .
C16 C 0.8167(4) 0.0619(10) 0.1920(5) 0.129(3) Uani 1 1 d . . . . .
H16A H 0.851185 0.041713 0.166110 0.155 Uiso 1 1 calc R U . . .
H16B H 0.835143 0.026889 0.246240 0.155 Uiso 1 1 calc R U . . .
C17 C 0.8092(3) 0.2139(9) 0.1954(5) 0.130(3) Uani 1 1 d . . . . .
H17A H 0.778271 0.246748 0.144922 0.195 Uiso 1 1 calc R U . . .
H17B H 0.854591 0.256659 0.206797 0.195 Uiso 1 1 calc R U . . .
H17C H 0.790015 0.237025 0.236672 0.195 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 2.003(2) . ?
Co1 O2 2.007(2) 5_665 ?
Co1 N3 2.134(2) 3_445 ?
Co1 N2 2.151(2) . ?
Co1 O3 2.208(3) . ?
Co1 O4 2.210(3) . ?
O1 C1 1.252(4) . ?
O2 C1 1.266(4) . ?
C1 C4 1.505(4) . ?
N1 C2 1.384(7) . ?
N1 H1 0.86(5) . ?
N1 H1 0.86(5) 2_654 ?
C2 C3 1.393(4) . ?
C2 C3 1.393(4) 2_654 ?
C3 C4 1.384(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(4) . ?
C5 H5 0.9500 . ?
N2 C10X 1.317(9) . ?
N2 C6 1.333(8) . ?
N2 C6X 1.338(12) . ?
N2 C10 1.372(6) . ?
C6 C7 1.373(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(9) . ?
C7 H7 0.9500 . ?
C8 C7X 1.374(12) . ?
C8 C9 1.385(6) . ?
C8 C9X 1.440(9) . ?
C8 C13 1.483(4) . ?
C9 C10 1.368(7) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C6X C7X 1.372(12) . ?
C6X H6X 0.9500 . ?
C7X H7X 0.9500 . ?
C9X C10X 1.392(10) . ?
C9X H9X 0.9500 . ?
C10X H10X 0.9500 . ?
N3 C15X 1.327(12) . ?
N3 C11 1.331(7) . ?
N3 C15 1.349(8) . ?
N3 C11X 1.361(11) . ?
C11 C12 1.380(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.406(8) . ?
C12 H12 0.9500 . ?
C13 C14X 1.369(13) . ?
C13 C14 1.390(8) . ?
C13 C12X 1.418(11) . ?
C14 C15 1.380(8) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C11X C12X 1.376(12) . ?
C11X H11X 0.9500 . ?
C12X H12X 0.9500 . ?
C14X C15X 1.377(13) . ?
C14X H14X 0.9500 . ?
C15X H15X 0.9500 . ?
O3 N4 1.271(5) . ?
O4 N4 1.249(5) . ?
N4 O5 1.232(5) . ?
O6 C16 1.337(9) . ?
O6 H6A 0.8400 . ?
C16 C17 1.510(12) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 126.48(11) . 5_665 ?
O1 Co1 N3 88.72(9) . 3_445 ?
O2 Co1 N3 87.88(9) 5_665 3_445 ?
O1 Co1 N2 90.68(9) . . ?
O2 Co1 N2 93.10(9) 5_665 . ?
N3 Co1 N2 179.03(10) 3_445 . ?
O1 Co1 O3 89.63(12) . . ?
O2 Co1 O3 143.77(12) 5_665 . ?
N3 Co1 O3 90.49(10) 3_445 . ?
N2 Co1 O3 88.74(11) . . ?
O1 Co1 O4 147.31(13) . . ?
O2 Co1 O4 86.19(12) 5_665 . ?
N3 Co1 O4 91.65(10) 3_445 . ?
N2 Co1 O4 88.44(10) . . ?
O3 Co1 O4 57.68(12) . . ?
C1 O1 Co1 134.9(2) . . ?
C1 O2 Co1 142.5(2) . 5_665 ?
O1 C1 O2 125.7(3) . . ?
O1 C1 C4 117.6(3) . . ?
O2 C1 C4 116.6(3) . . ?
C2 N1 H1 127(3) . . ?
C2 N1 H1 127(3) . 2_654 ?
H1 N1 H1 105(7) . 2_654 ?
N1 C2 C3 120.9(2) . . ?
N1 C2 C3 120.9(2) . 2_654 ?
C3 C2 C3 118.2(4) . 2_654 ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 C1 118.9(3) . . ?
C5 C4 C1 120.9(3) . . ?
C4 C5 C4 118.9(4) . 2_654 ?
C4 C5 H5 120.5 . . ?
C4 C5 H5 120.5 2_654 . ?
C10X N2 C6X 117.3(8) . . ?
C6 N2 C10 114.8(5) . . ?
C10X N2 Co1 119.5(4) . . ?
C6 N2 Co1 121.4(5) . . ?
C6X N2 Co1 122.2(7) . . ?
C10 N2 Co1 123.5(3) . . ?
N2 C6 C7 123.3(8) . . ?
N2 C6 H6 118.4 . . ?
C7 C6 H6 118.4 . . ?
C6 C7 C8 120.7(8) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C9 117.0(5) . . ?
C7X C8 C9X 114.8(8) . . ?
C7X C8 C13 122.7(7) . . ?
C7 C8 C13 122.8(5) . . ?
C9 C8 C13 119.8(3) . . ?
C9X C8 C13 121.5(4) . . ?
C10 C9 C8 118.4(5) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 N2 124.8(5) . . ?
C9 C10 H10 117.6 . . ?
N2 C10 H10 117.6 . . ?
N2 C6X C7X 123.1(14) . . ?
N2 C6X H6X 118.4 . . ?
C7X C6X H6X 118.4 . . ?
C6X C7X C8 120.9(14) . . ?
C6X C7X H7X 119.6 . . ?
C8 C7X H7X 119.6 . . ?
C10X C9X C8 118.7(8) . . ?
C10X C9X H9X 120.6 . . ?
C8 C9X H9X 120.6 . . ?
N2 C10X C9X 123.3(8) . . ?
N2 C10X H10X 118.4 . . ?
C9X C10X H10X 118.4 . . ?
C11 N3 C15 117.0(6) . . ?
C15X N3 C11X 115.5(9) . . ?
C11 N3 Co1 121.8(4) . 3 ?
C15 N3 Co1 121.2(4) . 3 ?
N3 C11 C12 123.8(8) . . ?
N3 C11 H11 118.1 . . ?
C12 C11 H11 118.1 . . ?
C11 C12 C13 119.2(7) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 116.6(5) . . ?
C14X C13 C12X 118.0(9) . . ?
C14X C13 C8 121.2(7) . . ?
C14 C13 C8 121.2(5) . . ?
C12 C13 C8 122.1(4) . . ?
C12X C13 C8 120.8(6) . . ?
C15 C14 C13 120.1(8) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
N3 C15 C14 122.9(8) . . ?
N3 C15 H15 118.5 . . ?
C14 C15 H15 118.5 . . ?
N3 C11X C12X 124.2(12) . . ?
N3 C11X H11X 117.9 . . ?
C12X C11X H11X 117.9 . . ?
C11X C12X C13 118.0(11) . . ?
C11X C12X H12X 121.0 . . ?
C13 C12X H12X 121.0 . . ?
C13 C14X C15X 119.2(14) . . ?
C13 C14X H14X 120.4 . . ?
C15X C14X H14X 120.4 . . ?
N3 C15X C14X 125.1(15) . . ?
N3 C15X H15X 117.5 . . ?
C14X C15X H15X 117.5 . . ?
N4 O3 Co1 93.1(2) . . ?
N4 O4 Co1 93.6(2) . . ?
O5 N4 O4 123.7(5) . . ?
O5 N4 O3 120.9(5) . . ?
O4 N4 O3 115.5(3) . . ?
C16 O6 H6A 109.5 . . ?
O6 C16 C17 115.4(7) . . ?
O6 C16 H16A 108.4 . . ?
C17 C16 H16A 108.4 . . ?
O6 C16 H16B 108.4 . . ?
C17 C16 H16B 108.4 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 O1 C1 O2 -20.7(5) . . . . ?
Co1 O1 C1 C4 160.2(2) . . . . ?
Co1 O2 C1 O1 -20.5(6) 5_665 . . . ?
Co1 O2 C1 C4 158.6(3) 5_665 . . . ?
N1 C2 C3 C4 -179.6(2) . . . . ?
C3 C2 C3 C4 0.4(2) 2_654 . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C2 C3 C4 C1 178.9(2) . . . . ?
O1 C1 C4 C3 5.0(4) . . . . ?
O2 C1 C4 C3 -174.2(3) . . . . ?
O1 C1 C4 C5 -175.2(2) . . . . ?
O2 C1 C4 C5 5.6(4) . . . . ?
C3 C4 C5 C4 0.4(2) . . . 2_654 ?
C1 C4 C5 C4 -179.4(3) . . . 2_654 ?
C10 N2 C6 C7 7.7(10) . . . . ?
Co1 N2 C6 C7 -178.5(7) . . . . ?
N2 C6 C7 C8 0.8(13) . . . . ?
C6 C7 C8 C9 -8.5(13) . . . . ?
C6 C7 C8 C13 179.5(6) . . . . ?
C7 C8 C9 C10 7.1(10) . . . . ?
C13 C8 C9 C10 179.4(5) . . . . ?
C8 C9 C10 N2 1.7(10) . . . . ?
C6 N2 C10 C9 -9.1(9) . . . . ?
Co1 N2 C10 C9 177.2(5) . . . . ?
C10X N2 C6X C7X -6.9(14) . . . . ?
Co1 N2 C6X C7X -175.4(9) . . . . ?
N2 C6X C7X C8 -5.3(17) . . . . ?
C9X C8 C7X C6X 13.8(19) . . . . ?
C13 C8 C7X C6X -177.4(8) . . . . ?
C7X C8 C9X C10X -10.9(17) . . . . ?
C13 C8 C9X C10X -179.9(9) . . . . ?
C6X N2 C10X C9X 9.7(17) . . . . ?
Co1 N2 C10X C9X 178.5(9) . . . . ?
C8 C9X C10X N2 -0.7(18) . . . . ?
C15 N3 C11 C12 3.0(10) . . . . ?
Co1 N3 C11 C12 -179.3(5) 3 . . . ?
N3 C11 C12 C13 2.5(10) . . . . ?
C11 C12 C13 C14 -6.0(10) . . . . ?
C11 C12 C13 C8 178.5(5) . . . . ?
C7X C8 C13 C14X -176.6(16) . . . . ?
C9X C8 C13 C14X -8.5(14) . . . . ?
C7 C8 C13 C14 -176.6(10) . . . . ?
C9 C8 C13 C14 11.6(9) . . . . ?
C7 C8 C13 C12 -1.3(9) . . . . ?
C9 C8 C13 C12 -173.1(5) . . . . ?
C7X C8 C13 C12X 5.6(15) . . . . ?
C9X C8 C13 C12X 173.7(9) . . . . ?
C12 C13 C14 C15 4.1(14) . . . . ?
C8 C13 C14 C15 179.7(8) . . . . ?
C11 N3 C15 C14 -5.0(14) . . . . ?
Co1 N3 C15 C14 177.4(9) 3 . . . ?
C13 C14 C15 N3 1.4(17) . . . . ?
C15X N3 C11X C12X 0.4(15) . . . . ?
Co1 N3 C11X C12X -178.0(8) 3 . . . ?
N3 C11X C12X C13 0.0(14) . . . . ?
C14X C13 C12X C11X 1.7(18) . . . . ?
C8 C13 C12X C11X 179.6(7) . . . . ?
C12X C13 C14X C15X -4(2) . . . . ?
C8 C13 C14X C15X 178.5(14) . . . . ?
C11X N3 C15X C14X -3(2) . . . . ?
Co1 N3 C15X C14X 175.8(16) 3 . . . ?
C13 C14X C15X N3 4(3) . . . . ?
Co1 O4 N4 O5 177.2(4) . . . . ?
Co1 O4 N4 O3 -3.3(3) . . . . ?
Co1 O3 N4 O5 -177.2(4) . . . . ?
Co1 O3 N4 O4 3.3(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 O4 0.86(5) 2.47(5) 3.287(4) 159(5) 5_655 yes
N1 H1 N4 0.86(5) 2.61(5) 3.370(4) 148(5) 5_655 yes
O6 H6A O5 0.84 2.07 2.819(6) 147.8 . yes

_refine_diff_density_max         0.890
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.098


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylformamide/ethanol'
####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 2207275'
loop_
_audit_author_name
_audit_author_address
'Mark Elsegood'
;Loughborough University
United Kingdom
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT043_cr496               
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..     221.29 Check 
RESPONSE: Accounted for by Squeezed solvent
;
_vrf_PLAT602_cr496               
;
PROBLEM: Solvent Accessible VOID(S) in Structure ........          ! Check 
RESPONSE: Squeezed
;
_vrf_PLAT971_cr496               
;
PROBLEM: Check Calcd Resid. Dens.  1.05Ang From N2              4.64 eA-3  
RESPONSE: Unresolved disorder in the linker.
;
_vrf_PLAT094_cr496               
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       5.86 Report
RESPONSE: Unresolved disorder and not the best data set.
;
_vrf_PLAT250_cr496               
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.3 Note  
RESPONSE: Unresolved disorder and not the best data set.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 Cd N4 O4, 3(C3 H7 N O)'
_chemical_formula_sum            'C27 H34 Cd N6 O7'
_chemical_formula_weight         667.00

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

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

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

_cell_length_a                   14.0579(14)
_cell_length_b                   17.2541(17)
_cell_length_c                   11.6948(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2836.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3057
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      25.78

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.826
_shelx_estimated_absorpt_T_min   0.673
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_process_details   'SADABS v20012/1, Sheldrick, G.M., (2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24395
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.741
_diffrn_reflns_theta_max         28.356
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7074
_reflns_number_gt                5318
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
'Refined as a 2-component inversion twin.,SQUEEZE'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0976P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.45(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7074
_refine_ls_number_parameters     273
_refine_ls_number_restraints     300
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.1640
_refine_ls_wR_factor_gt          0.1569
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.022
_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 0.86408(4) 0.48452(3) 0.02036(6) 0.03344(19) Uani 1 1 d . . . . .
N1 N 0.8668(5) 0.4833(4) 0.2191(4) 0.0263(12) Uani 1 1 d . . . . .
C1 C 0.8614(15) 0.4181(7) 0.2805(11) 0.082(4) Uani 1 1 d . . . . .
H1 H 0.850828 0.370878 0.240796 0.099 Uiso 1 1 calc R U . . .
C2 C 0.8698(15) 0.4151(6) 0.3935(11) 0.089(5) Uani 1 1 d . . . . .
H2 H 0.877893 0.366521 0.430429 0.107 Uiso 1 1 calc R U . . .
C3 C 0.8669(6) 0.4803(5) 0.4559(8) 0.046(2) Uani 1 1 d . . . . .
C4 C 0.8662(17) 0.5462(8) 0.3975(11) 0.108(6) Uani 1 1 d . . . . .
H4 H 0.860776 0.594041 0.437157 0.130 Uiso 1 1 calc R U . . .
C5 C 0.8734(16) 0.5459(7) 0.2794(10) 0.093(5) Uani 1 1 d . . . . .
H5 H 0.883578 0.593750 0.241091 0.112 Uiso 1 1 calc R U . . .
N2 N 0.8725(5) 0.4837(5) 0.8161(8) 0.0540(18) Uani 1 1 d . U . . .
C6 C 0.9043(9) 0.4233(6) 0.7645(10) 0.059(3) Uani 1 1 d . U . . .
H6 H 0.928469 0.381007 0.807554 0.071 Uiso 1 1 calc R U . . .
C7 C 0.9034(9) 0.4199(7) 0.6476(11) 0.060(3) Uani 1 1 d . U . . .
H7 H 0.928427 0.375611 0.609871 0.072 Uiso 1 1 calc R U . . .
C8 C 0.8662(7) 0.4809(5) 0.5833(8) 0.0438(18) Uani 1 1 d . U . . .
C9 C 0.8309(10) 0.5435(8) 0.6476(12) 0.075(4) Uani 1 1 d . U . . .
H9 H 0.807393 0.588236 0.609472 0.090 Uiso 1 1 calc R U . . .
C10 C 0.8299(9) 0.5406(7) 0.7664(11) 0.065(3) Uani 1 1 d . U . . .
H10 H 0.798678 0.579570 0.809794 0.078 Uiso 1 1 calc R U . . .
C11 C 0.6124(5) 0.3520(4) 0.0009(13) 0.054(3) Uani 1 1 d D U . . .
C12 C 0.6276(5) 0.2727(4) -0.0050(9) 0.044(2) Uani 1 1 d D U . . .
H12 H 0.690385 0.252454 -0.001935 0.053 Uiso 1 1 calc R U . . .
C13 C 0.5494(5) 0.2225(4) -0.0156(11) 0.041(2) Uani 1 1 d D U . . .
C14 C 0.4579(7) 0.2517(6) -0.0348(18) 0.038(4) Uani 0.698(14) 1 d D U P A 1
H14 H 0.406028 0.216938 -0.044235 0.046 Uiso 0.698(14) 1 calc R U P A 1
C15 C 0.4423(7) 0.3314(6) -0.0403(17) 0.042(3) Uani 0.698(14) 1 d D U P A 1
N3 N 0.3533(7) 0.3631(6) -0.0604(13) 0.054(4) Uani 0.698(14) 1 d D U P A 1
C16 C 0.5221(7) 0.3821(7) -0.0243(18) 0.045(3) Uani 0.698(14) 1 d D U P A 1
H16 H 0.513747 0.436529 -0.030785 0.054 Uiso 0.698(14) 1 calc R U P A 1
C14X C 0.4597(16) 0.2509(13) 0.029(4) 0.046(6) Uani 0.302(14) 1 d D U P A 2
H14X H 0.410816 0.214588 0.045371 0.055 Uiso 0.302(14) 1 calc R U P A 2
C15X C 0.4422(15) 0.3295(14) 0.048(4) 0.050(5) Uani 0.302(14) 1 d D U P A 2
N3X N 0.3514(15) 0.3590(15) 0.070(3) 0.064(8) Uani 0.302(14) 1 d D U P A 2
C16X C 0.5254(15) 0.3779(15) 0.057(4) 0.047(5) Uani 0.302(14) 1 d D U P A 2
H16X H 0.523601 0.425313 0.098228 0.057 Uiso 0.302(14) 1 calc R U P A 2
C17 C 0.6968(5) 0.4050(4) 0.0148(10) 0.036(2) Uani 1 1 d . . . . .
O1 O 0.6860(4) 0.4769(3) 0.0114(7) 0.0537(18) Uani 1 1 d . . . . .
O2 O 0.7770(4) 0.3733(3) 0.0206(7) 0.0399(15) Uani 1 1 d . . . . .
C18 C 0.5687(5) 0.1383(4) -0.0173(9) 0.0312(18) Uani 1 1 d . . . . .
O3 O 0.6549(4) 0.1158(3) -0.0178(7) 0.0420(15) Uani 1 1 d . . . . .
O4 O 0.5012(4) 0.0895(3) -0.0188(7) 0.0463(16) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 O2 2.277(5) . ?
Cd1 O3 2.281(5) 3_655 ?
Cd1 O4 2.313(5) 4 ?
Cd1 N1 2.325(5) . ?
Cd1 N2 2.392(9) 1_554 ?
Cd1 O1 2.508(5) . ?
Cd1 O4 2.621(5) 3_655 ?
Cd1 C17 2.724(7) . ?
N1 C5 1.295(13) . ?
N1 C1 1.336(14) . ?
C1 C2 1.328(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.341(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.326(15) . ?
C3 C8 1.490(13) . ?
C4 C5 1.385(18) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
N2 C6 1.284(13) . ?
N2 C10 1.288(14) . ?
C6 C7 1.369(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.408(14) . ?
C9 C10 1.390(19) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.387(11) . ?
C11 C16 1.402(13) . ?
C11 C16X 1.46(2) . ?
C11 C17 1.507(10) . ?
C12 C13 1.405(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(12) . ?
C13 C14X 1.45(2) . ?
C13 C18 1.479(10) . ?
C14 C15 1.395(13) . ?
C14 H14 0.9500 . ?
C15 N3 1.386(14) . ?
C15 C16 1.434(13) . ?
C16 H16 0.9500 . ?
C14X C15X 1.40(2) . ?
C14X H14X 0.9500 . ?
C15X N3X 1.40(2) . ?
C15X C16X 1.44(2) . ?
C16X H16X 0.9500 . ?
C17 O1 1.251(9) . ?
C17 O2 1.256(9) . ?
C18 O4 1.268(9) . ?
C18 O3 1.273(9) . ?

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
O2 Cd1 O3 140.75(18) . 3_655 ?
O2 Cd1 O4 88.98(19) . 4 ?
O3 Cd1 O4 130.25(19) 3_655 4 ?
O2 Cd1 N1 90.0(3) . . ?
O3 Cd1 N1 91.4(3) 3_655 . ?
O4 Cd1 N1 89.4(3) 4 . ?
O2 Cd1 N2 91.3(3) . 1_554 ?
O3 Cd1 N2 89.9(3) 3_655 1_554 ?
O4 Cd1 N2 87.0(3) 4 1_554 ?
N1 Cd1 N2 176.1(2) . 1_554 ?
O2 Cd1 O1 54.53(18) . . ?
O3 Cd1 O1 86.24(18) 3_655 . ?
O4 Cd1 O1 143.37(18) 4 . ?
N1 Cd1 O1 93.3(2) . . ?
N2 Cd1 O1 90.4(3) 1_554 . ?
O2 Cd1 O4 166.24(18) . 3_655 ?
O3 Cd1 O4 52.99(17) 3_655 3_655 ?
O4 Cd1 O4 77.3(2) 4 3_655 ?
N1 Cd1 O4 90.1(2) . 3_655 ?
N2 Cd1 O4 87.8(3) 1_554 3_655 ?
O1 Cd1 O4 139.17(18) . 3_655 ?
O2 Cd1 C17 27.3(2) . . ?
O3 Cd1 C17 113.5(2) 3_655 . ?
O4 Cd1 C17 116.2(2) 4 . ?
N1 Cd1 C17 91.9(3) . . ?
N2 Cd1 C17 90.9(3) 1_554 . ?
O1 Cd1 C17 27.3(2) . . ?
O4 Cd1 C17 166.4(2) 3_655 . ?
C5 N1 C1 114.4(8) . . ?
C5 N1 Cd1 122.6(7) . . ?
C1 N1 Cd1 123.0(7) . . ?
C2 C1 N1 124.2(11) . . ?
C2 C1 H1 117.9 . . ?
N1 C1 H1 117.9 . . ?
C1 C2 C3 120.4(11) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 116.1(10) . . ?
C4 C3 C8 120.6(9) . . ?
C2 C3 C8 123.4(9) . . ?
C3 C4 C5 120.7(11) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N1 C5 C4 122.7(12) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C6 N2 C10 124.6(11) . . ?
C6 N2 Cd1 119.4(8) . 1_556 ?
C10 N2 Cd1 115.1(8) . 1_556 ?
N2 C6 C7 120.1(11) . . ?
N2 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 120.6(10) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 115.1(10) . . ?
C7 C8 C3 122.1(9) . . ?
C9 C8 C3 122.8(10) . . ?
C10 C9 C8 120.6(12) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
N2 C10 C9 118.3(10) . . ?
N2 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C12 C11 C16 119.6(8) . . ?
C12 C11 C16X 117.0(13) . . ?
C12 C11 C17 118.9(7) . . ?
C16 C11 C17 120.7(7) . . ?
C16X C11 C17 115.2(12) . . ?
C11 C12 C13 119.4(7) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 120.8(8) . . ?
C12 C13 C14X 116.2(13) . . ?
C14 C13 C18 121.3(8) . . ?
C12 C13 C18 117.6(7) . . ?
C14X C13 C18 119.8(12) . . ?
C15 C14 C13 120.4(9) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
N3 C15 C14 122.6(9) . . ?
N3 C15 C16 119.2(9) . . ?
C14 C15 C16 118.2(9) . . ?
C11 C16 C15 120.7(9) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C15X C14X C13 122.6(19) . . ?
C15X C14X H14X 118.7 . . ?
C13 C14X H14X 118.7 . . ?
C14X C15X N3X 123.0(19) . . ?
C14X C15X C16X 115.6(18) . . ?
N3X C15X C16X 121.0(19) . . ?
C15X C16X C11 118(2) . . ?
C15X C16X H16X 121.0 . . ?
C11 C16X H16X 121.0 . . ?
O1 C17 O2 122.9(6) . . ?
O1 C17 C11 120.3(7) . . ?
O2 C17 C11 116.6(7) . . ?
O1 C17 Cd1 66.7(4) . . ?
O2 C17 Cd1 56.1(4) . . ?
C11 C17 Cd1 171.2(7) . . ?
C17 O1 Cd1 86.0(4) . . ?
C17 O2 Cd1 96.6(4) . . ?
O4 C18 O3 120.7(6) . . ?
O4 C18 C13 121.0(7) . . ?
O3 C18 C13 118.3(6) . . ?
C18 O3 Cd1 101.0(4) . 3_645 ?
C18 O4 Cd1 172.0(5) . 4_455 ?
C18 O4 Cd1 85.3(4) . 3_645 ?
Cd1 O4 Cd1 102.7(2) 4_455 3_645 ?

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
C5 N1 C1 C2 -5(2) . . . . ?
Cd1 N1 C1 C2 174.8(16) . . . . ?
N1 C1 C2 C3 12(3) . . . . ?
C1 C2 C3 C4 -7(2) . . . . ?
C1 C2 C3 C8 173.7(16) . . . . ?
C2 C3 C4 C5 -3(3) . . . . ?
C8 C3 C4 C5 175.6(17) . . . . ?
C1 N1 C5 C4 -6(2) . . . . ?
Cd1 N1 C5 C4 173.9(17) . . . . ?
C3 C4 C5 N1 11(4) . . . . ?
C10 N2 C6 C7 7.2(18) . . . . ?
Cd1 N2 C6 C7 175.5(9) 1_556 . . . ?
N2 C6 C7 C8 -1.4(19) . . . . ?
C6 C7 C8 C9 -0.2(18) . . . . ?
C6 C7 C8 C3 178.0(11) . . . . ?
C4 C3 C8 C7 -154.2(15) . . . . ?
C2 C3 C8 C7 24.7(19) . . . . ?
C4 C3 C8 C9 24(2) . . . . ?
C2 C3 C8 C9 -157.2(15) . . . . ?
C7 C8 C9 C10 -3.2(18) . . . . ?
C3 C8 C9 C10 178.6(11) . . . . ?
C6 N2 C10 C9 -10.5(18) . . . . ?
Cd1 N2 C10 C9 -179.3(10) 1_556 . . . ?
C8 C9 C10 N2 8(2) . . . . ?
C16 C11 C12 C13 -11(2) . . . . ?
C16X C11 C12 C13 33(2) . . . . ?
C17 C11 C12 C13 178.7(10) . . . . ?
C11 C12 C13 C14 8(2) . . . . ?
C11 C12 C13 C14X -26(3) . . . . ?
C11 C12 C13 C18 -177.8(11) . . . . ?
C12 C13 C14 C15 -2(3) . . . . ?
C18 C13 C14 C15 -175.8(14) . . . . ?
C13 C14 C15 N3 179.2(18) . . . . ?
C13 C14 C15 C16 -1(3) . . . . ?
C12 C11 C16 C15 9(3) . . . . ?
C17 C11 C16 C15 178.5(16) . . . . ?
N3 C15 C16 C11 177.4(16) . . . . ?
C14 C15 C16 C11 -3(3) . . . . ?
C12 C13 C14X C15X 19(5) . . . . ?
C18 C13 C14X C15X 171(4) . . . . ?
C13 C14X C15X N3X 168(4) . . . . ?
C13 C14X C15X C16X -19(7) . . . . ?
C14X C15X C16X C11 25(6) . . . . ?
N3X C15X C16X C11 -162(3) . . . . ?
C12 C11 C16X C15X -32(4) . . . . ?
C17 C11 C16X C15X -179(3) . . . . ?
C12 C11 C17 O1 174.4(12) . . . . ?
C16 C11 C17 O1 5(2) . . . . ?
C16X C11 C17 O1 -39(2) . . . . ?
C12 C11 C17 O2 -0.2(17) . . . . ?
C16 C11 C17 O2 -169.9(14) . . . . ?
C16X C11 C17 O2 146(2) . . . . ?
O2 C17 O1 Cd1 0.2(11) . . . . ?
C11 C17 O1 Cd1 -174.0(10) . . . . ?
O1 C17 O2 Cd1 -0.2(12) . . . . ?
C11 C17 O2 Cd1 174.2(9) . . . . ?
C14 C13 C18 O4 -11(2) . . . . ?
C12 C13 C18 O4 175.2(10) . . . . ?
C14X C13 C18 O4 24(3) . . . . ?
C14 C13 C18 O3 168.8(14) . . . . ?
C12 C13 C18 O3 -5.2(17) . . . . ?
C14X C13 C18 O3 -156(2) . . . . ?
O4 C18 O3 Cd1 -0.4(11) . . . 3_645 ?
C13 C18 O3 Cd1 180.0(9) . . . 3_645 ?
O3 C18 O4 Cd1 0.3(10) . . . 3_645 ?
C13 C18 O4 Cd1 179.9(10) . . . 3_645 ?

_refine_diff_density_max         4.529
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.157


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylformamide/ethanol'
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2207271'
loop_
_audit_author_name
_audit_author_address
'Mark Elsegood'
;Loughborough University
United Kingdom
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT043_cr484               
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..     176.26 Check 
RESPONSE: Discrepancy due to Squeezed solvent.
;
_vrf_PLAT602_cr484               
;
PROBLEM: Solvent Accessible VOID(S) in Structure ........          ! Check 
RESPONSE: Squeezed
;
_vrf_PLAT049_cr484               
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.9250 Check 
RESPONSE: Not true when solvent of crystallisation taken into account.
;
_vrf_PLAT430_cr484               
;
PROBLEM: Short Inter D...A Contact  O2       ..N5X      .       2.86 Ang.  
RESPONSE: There is an H-bond here.
;
_vrf_PLAT911_cr484               
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        426 Report
RESPONSE: Not a great data set, reflections omitted during data reduction.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 Co N5 O4, 2(C4 H9 N O)'
_chemical_formula_sum            'C26 H31 Co N7 O6'
_chemical_formula_weight         596.51

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

_space_group_crystal_system      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                   13.20(2)
_cell_length_b                   16.71(2)
_cell_length_c                   14.11(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.24(3)
_cell_angle_gamma                90
_cell_volume                     3017(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7573
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      31.2

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             1244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.618
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   'Rigaku CrystalClear-SM Expert 2.0 r13'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ CCD (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            13115
_diffrn_reflns_av_unetI/netI     0.0982
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.252
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measured_fraction_theta_full 0.921
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_Laue_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 0.921
_reflns_number_total             6401
_reflns_number_gt                4462
_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       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2131P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6401
_refine_ls_number_parameters     290
_refine_ls_number_restraints     252
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.1056
_refine_ls_wR_factor_ref         0.3371
_refine_ls_wR_factor_gt          0.3225
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.100
_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 0.50349(5) 0.97384(3) 0.64090(4) 0.0263(3) Uani 1 1 d . . . . .
N1 N 0.3383(4) 0.9743(2) 0.6248(3) 0.0408(11) Uani 1 1 d . . . . .
C1 C 0.2796(5) 0.9126(5) 0.5844(6) 0.068(2) Uani 1 1 d . . . . .
H1 H 0.311019 0.870676 0.556102 0.081 Uiso 1 1 calc R U . . .
C2 C 0.1781(7) 0.9075(7) 0.5823(7) 0.090(3) Uani 1 1 d . . . . .
H2 H 0.141417 0.860681 0.555014 0.108 Uiso 1 1 calc R U . . .
C3 C 0.1255(6) 0.9637(5) 0.6158(6) 0.0620(18) Uani 1 1 d . . . . .
C4 C 0.1830(6) 1.0331(5) 0.6504(6) 0.068(2) Uani 1 1 d . . . . .
H4 H 0.148570 1.078670 0.667950 0.081 Uiso 1 1 calc R U . . .
C5 C 0.2913(6) 1.0353(4) 0.6591(6) 0.0602(18) Uani 1 1 d . . . . .
H5 H 0.331221 1.079789 0.689216 0.072 Uiso 1 1 calc R U . . .
N2 N 0.0210(6) 0.9562(5) 0.6154(5) 0.0720(18) Uani 1 1 d . . . . .
N3 N -0.0162(6) 0.9988(5) 0.6580(5) 0.0736(19) Uani 1 1 d . . . . .
N4 N -0.3346(4) 0.9761(2) 0.6543(3) 0.0378(10) Uani 1 1 d . . . . .
C8 C -0.2763(6) 1.0439(4) 0.6873(7) 0.074(2) Uani 1 1 d . . . . .
H8 H -0.311250 1.089311 0.704405 0.089 Uiso 1 1 calc R U . . .
C9 C -0.1684(7) 1.0489(5) 0.6966(6) 0.073(2) Uani 1 1 d . . . . .
H9 H -0.129449 1.092678 0.729899 0.088 Uiso 1 1 calc R U . . .
C10 C -0.1209(6) 0.9912(5) 0.6579(6) 0.0628(17) Uani 1 1 d . . . . .
C11 C -0.1820(6) 0.9212(5) 0.6146(5) 0.0671(19) Uani 1 1 d . . . . .
H11 H -0.151851 0.878964 0.585704 0.081 Uiso 1 1 calc R U . . .
C12 C -0.2854(5) 0.9199(4) 0.6179(5) 0.0518(14) Uani 1 1 d . . . . .
H12 H -0.324941 0.874130 0.591298 0.062 Uiso 1 1 calc R U . . .
C13 C 0.5127(5) 0.8459(3) 0.8839(4) 0.0409(12) Uani 1 1 d D U . . .
C14 C 0.5080(4) 0.7644(3) 0.8742(3) 0.0304(9) Uani 1 1 d D U . . .
H14 H 0.509529 0.740371 0.813595 0.036 Uiso 1 1 calc R U . . .
C15 C 0.5012(5) 0.7176(3) 0.9520(4) 0.0427(13) Uani 1 1 d D U . . .
C16 C 0.5198(11) 0.7544(5) 1.0457(6) 0.039(3) Uani 0.578(14) 1 d D U P A 1
H16 H 0.524903 0.721472 1.101568 0.047 Uiso 0.578(14) 1 calc R U P A 1
C17 C 0.5308(12) 0.8357(5) 1.0584(6) 0.042(3) Uani 0.578(14) 1 d D U P A 1
N5 N 0.5449(11) 0.8692(5) 1.1522(5) 0.055(3) Uani 0.578(14) 1 d D U P A 1
C18 C 0.5298(12) 0.8810(5) 0.9755(6) 0.041(3) Uani 0.578(14) 1 d D U P A 1
H18 H 0.541088 0.937063 0.981750 0.050 Uiso 0.578(14) 1 calc R U P A 1
C16X C 0.4693(14) 0.7529(6) 1.0320(8) 0.033(3) Uani 0.422(14) 1 d D U P A 2
H16X H 0.451448 0.719394 1.079893 0.040 Uiso 0.422(14) 1 calc R U P A 2
C17X C 0.4639(15) 0.8350(6) 1.0410(7) 0.038(3) Uani 0.422(14) 1 d D U P A 2
N5X N 0.4454(16) 0.8661(6) 1.1286(8) 0.059(5) Uani 0.422(14) 1 d D U P A 2
C18X C 0.4763(14) 0.8787(7) 0.9615(8) 0.035(3) Uani 0.422(14) 1 d D U P A 2
H18X H 0.459288 0.933983 0.958886 0.043 Uiso 0.422(14) 1 calc R U P A 2
C19 C 0.5175(4) 0.8976(3) 0.7974(3) 0.0331(10) Uani 1 1 d . . . . .
O1 O 0.5197(4) 0.86312(19) 0.7195(2) 0.0407(10) Uani 1 1 d . . . . .
O2 O 0.5192(4) 0.97264(17) 0.8030(3) 0.0401(10) Uani 1 1 d . . . . .
C20 C 0.4925(4) 0.6269(3) 0.9429(3) 0.0301(9) Uani 1 1 d . . . . .
O3 O 0.4774(3) 0.58795(18) 1.0139(2) 0.0359(8) Uani 1 1 d . . . . .
O4 O 0.5031(3) 0.59683(19) 0.8647(2) 0.0337(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O3 2.023(4) 4_575 ?
Co1 O4 2.058(4) 2_656 ?
Co1 N4 2.098(6) 1_655 ?
Co1 N1 2.136(6) . ?
Co1 O1 2.141(4) . ?
Co1 O2 2.245(5) . ?
Co1 C19 2.517(5) . ?
N1 C1 1.331(7) . ?
N1 C5 1.343(8) . ?
C1 C2 1.336(11) . ?
C1 H1 0.9500 . ?
C2 C3 1.322(12) . ?
C2 H2 0.9500 . ?
C3 N2 1.384(11) . ?
C3 C4 1.407(11) . ?
C4 C5 1.404(11) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
N2 N3 1.121(10) . ?
N3 C10 1.387(12) . ?
N4 C12 1.316(8) . ?
N4 C8 1.384(8) . ?
C8 C9 1.401(12) . ?
C8 H8 0.9500 . ?
C9 C10 1.336(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.467(11) . ?
C11 C12 1.377(10) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.368(7) . ?
C13 C18 1.386(9) . ?
C13 C18X 1.409(12) . ?
C13 C19 1.509(7) . ?
C14 C15 1.368(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.424(10) . ?
C15 C16X 1.426(11) . ?
C15 C20 1.522(7) . ?
C16 C17 1.373(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(11) . ?
C17 N5 1.406(10) . ?
C18 H18 0.9500 . ?
C16X C17X 1.381(12) . ?
C16X H16X 0.9500 . ?
C17X C18X 1.381(12) . ?
C17X N5X 1.417(12) . ?
C18X H18X 0.9500 . ?
C19 O1 1.248(6) . ?
C19 O2 1.257(6) . ?
C20 O3 1.251(5) . ?
C20 O4 1.251(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Co1 O4 118.63(13) 4_575 2_656 ?
O3 Co1 N4 92.11(18) 4_575 1_655 ?
O4 Co1 N4 91.03(16) 2_656 1_655 ?
O3 Co1 N1 87.73(17) 4_575 . ?
O4 Co1 N1 87.71(15) 2_656 . ?
N4 Co1 N1 178.47(16) 1_655 . ?
O3 Co1 O1 89.50(15) 4_575 . ?
O4 Co1 O1 151.79(12) 2_656 . ?
N4 Co1 O1 89.93(17) 1_655 . ?
N1 Co1 O1 91.58(17) . . ?
O3 Co1 O2 148.29(13) 4_575 . ?
O4 Co1 O2 92.34(11) 2_656 . ?
N4 Co1 O2 94.09(18) 1_655 . ?
N1 Co1 O2 86.83(18) . . ?
O1 Co1 O2 59.48(12) . . ?
O3 Co1 C19 118.59(17) 4_575 . ?
O4 Co1 C19 122.21(15) 2_656 . ?
N4 Co1 C19 94.39(18) 1_655 . ?
N1 Co1 C19 87.02(18) . . ?
O1 Co1 C19 29.70(14) . . ?
O2 Co1 C19 29.91(14) . . ?
C1 N1 C5 118.0(6) . . ?
C1 N1 Co1 120.9(4) . . ?
C5 N1 Co1 121.0(4) . . ?
N1 C1 C2 122.3(8) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 124.0(9) . . ?
C3 C2 H2 118.0 . . ?
C1 C2 H2 118.0 . . ?
C2 C3 N2 123.0(8) . . ?
C2 C3 C4 115.1(8) . . ?
N2 C3 C4 121.9(7) . . ?
C5 C4 C3 120.1(7) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
N1 C5 C4 120.0(7) . . ?
N1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
N3 N2 C3 120.6(9) . . ?
N2 N3 C10 120.7(9) . . ?
C12 N4 C8 115.3(6) . . ?
C12 N4 Co1 122.8(4) . 1_455 ?
C8 N4 Co1 121.0(4) . 1_455 ?
N4 C8 C9 123.3(7) . . ?
N4 C8 H8 118.3 . . ?
C9 C8 H8 118.3 . . ?
C10 C9 C8 119.2(8) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 N3 120.1(8) . . ?
C9 C10 C11 118.7(8) . . ?
N3 C10 C11 121.2(7) . . ?
C12 C11 C10 116.5(7) . . ?
C12 C11 H11 121.8 . . ?
C10 C11 H11 121.8 . . ?
N4 C12 C11 126.2(6) . . ?
N4 C12 H12 116.9 . . ?
C11 C12 H12 116.9 . . ?
C14 C13 C18 120.5(5) . . ?
C14 C13 C18X 116.7(7) . . ?
C14 C13 C19 119.9(4) . . ?
C18 C13 C19 118.8(6) . . ?
C18X C13 C19 119.7(6) . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 117.8(6) . . ?
C14 C15 C16X 119.3(6) . . ?
C14 C15 C20 121.4(4) . . ?
C16 C15 C20 120.0(5) . . ?
C16X C15 C20 116.5(6) . . ?
C17 C16 C15 122.5(8) . . ?
C17 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
C16 C17 C18 116.7(8) . . ?
C16 C17 N5 120.2(8) . . ?
C18 C17 N5 123.1(7) . . ?
C13 C18 C17 121.3(7) . . ?
C13 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C17X C16X C15 121.0(9) . . ?
C17X C16X H16X 119.5 . . ?
C15 C16X H16X 119.5 . . ?
C18X C17X C16X 115.6(9) . . ?
C18X C17X N5X 126.5(9) . . ?
C16X C17X N5X 117.9(9) . . ?
C17X C18X C13 123.8(10) . . ?
C17X C18X H18X 118.1 . . ?
C13 C18X H18X 118.1 . . ?
O1 C19 O2 120.7(4) . . ?
O1 C19 C13 117.6(4) . . ?
O2 C19 C13 121.7(4) . . ?
O1 C19 Co1 58.2(2) . . ?
O2 C19 Co1 63.0(2) . . ?
C13 C19 Co1 172.2(4) . . ?
C19 O1 Co1 92.1(3) . . ?
C19 O2 Co1 87.1(3) . . ?
O3 C20 O4 124.9(4) . . ?
O3 C20 C15 118.3(4) . . ?
O4 C20 C15 116.8(4) . . ?
C20 O3 Co1 161.6(4) . 4_576 ?
C20 O4 Co1 115.0(3) . 2_646 ?

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
C5 N1 C1 C2 -4.0(12) . . . . ?
Co1 N1 C1 C2 173.1(7) . . . . ?
N1 C1 C2 C3 2.8(16) . . . . ?
C1 C2 C3 N2 -178.2(9) . . . . ?
C1 C2 C3 C4 3.2(14) . . . . ?
C2 C3 C4 C5 -7.9(12) . . . . ?
N2 C3 C4 C5 173.4(8) . . . . ?
C1 N1 C5 C4 -1.0(11) . . . . ?
Co1 N1 C5 C4 -178.0(6) . . . . ?
C3 C4 C5 N1 7.0(12) . . . . ?
C2 C3 N2 N3 167.2(9) . . . . ?
C4 C3 N2 N3 -14.3(14) . . . . ?
C3 N2 N3 C10 -179.8(7) . . . . ?
C12 N4 C8 C9 -9.9(12) . . . . ?
Co1 N4 C8 C9 -179.3(7) 1_455 . . . ?
N4 C8 C9 C10 11.0(15) . . . . ?
C8 C9 C10 N3 173.8(8) . . . . ?
C8 C9 C10 C11 -5.2(13) . . . . ?
N2 N3 C10 C9 -169.9(9) . . . . ?
N2 N3 C10 C11 9.1(13) . . . . ?
C9 C10 C11 C12 -0.6(12) . . . . ?
N3 C10 C11 C12 -179.6(7) . . . . ?
C8 N4 C12 C11 3.6(11) . . . . ?
Co1 N4 C12 C11 172.7(6) 1_455 . . . ?
C10 C11 C12 N4 1.5(12) . . . . ?
C18 C13 C14 C15 11.9(12) . . . . ?
C18X C13 C14 C15 -20.3(11) . . . . ?
C19 C13 C14 C15 -178.5(6) . . . . ?
C13 C14 C15 C16 -12.2(11) . . . . ?
C13 C14 C15 C16X 17.8(12) . . . . ?
C13 C14 C15 C20 178.1(5) . . . . ?
C14 C15 C16 C17 8.6(16) . . . . ?
C20 C15 C16 C17 178.5(10) . . . . ?
C15 C16 C17 C18 -4.2(19) . . . . ?
C15 C16 C17 N5 177.5(12) . . . . ?
C14 C13 C18 C17 -7.4(17) . . . . ?
C19 C13 C18 C17 -177.2(10) . . . . ?
C16 C17 C18 C13 3.5(19) . . . . ?
N5 C17 C18 C13 -178.2(12) . . . . ?
C14 C15 C16X C17X -12.0(18) . . . . ?
C20 C15 C16X C17X -173.3(11) . . . . ?
C15 C16X C17X C18X 9(2) . . . . ?
C15 C16X C17X N5X -171.7(14) . . . . ?
C16X C17X C18X C13 -13(2) . . . . ?
N5X C17X C18X C13 168.3(15) . . . . ?
C14 C13 C18X C17X 18.2(19) . . . . ?
C19 C13 C18X C17X 176.4(12) . . . . ?
C14 C13 C19 O1 -1.8(9) . . . . ?
C18 C13 C19 O1 168.1(9) . . . . ?
C18X C13 C19 O1 -159.3(10) . . . . ?
C14 C13 C19 O2 178.2(5) . . . . ?
C18 C13 C19 O2 -12.0(11) . . . . ?
C18X C13 C19 O2 20.7(12) . . . . ?
O2 C19 O1 Co1 -7.5(6) . . . . ?
C13 C19 O1 Co1 172.4(5) . . . . ?
O1 C19 O2 Co1 7.2(6) . . . . ?
C13 C19 O2 Co1 -172.8(5) . . . . ?
C14 C15 C20 O3 -173.9(5) . . . . ?
C16 C15 C20 O3 16.6(10) . . . . ?
C16X C15 C20 O3 -13.1(11) . . . . ?
C14 C15 C20 O4 7.4(9) . . . . ?
C16 C15 C20 O4 -162.1(8) . . . . ?
C16X C15 C20 O4 168.2(9) . . . . ?
O4 C20 O3 Co1 90.5(10) . . . 4_576 ?
C15 C20 O3 Co1 -88.1(10) . . . 4_576 ?
O3 C20 O4 Co1 -1.0(7) . . . 2_646 ?
C15 C20 O4 Co1 177.6(4) . . . 2_646 ?

_refine_diff_density_max         1.031
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.128


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylacetamide/ethanol'
####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 2207276'
loop_
_audit_author_name
_audit_author_address
'Mark Elsegood'
;Loughborough University
United Kingdom
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT213_10                  
;
PROBLEM: Atom C7              has ADP max/min Ratio .....        6.2 prolat
RESPONSE: Twinned data and probably less than ideal absorption correction
of heavy atom compound with needle habit. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H15 Cd N3 O4, 4.5(C3 H7 N O)'
_chemical_formula_sum            'C33.50 H46.50 Cd N7.50 O8.50'
_chemical_formula_weight         802.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 '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                   13.9198(9)
_cell_length_b                   14.1580(8)
_cell_length_c                   17.2222(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.982(7)
_cell_angle_gamma                90
_cell_volume                     3209.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7700
_cell_measurement_theta_min      1.95
_cell_measurement_theta_max      33.27

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.840
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.750
_shelx_estimated_absorpt_T_min   0.572
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.270
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
; 
Rigaku FRE+ equipped with Arc)Sec VHF Varimax confocal mirrors and an UG2 
goniometer and HyPix 6000HE detector 
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_collimation    0.2
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            40289
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.1453
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.906
_diffrn_reflns_theta_max         33.064
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             14572
_reflns_number_gt                14081
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
"Refined as a 2-component twin. 180 deg rotation about 1 0 0 in direct space.',Twin,SQUEEZE"
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0655P)²+33.9148P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         14572
_refine_ls_number_parameters     255
_refine_ls_number_restraints     460
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0783
_refine_ls_wR_factor_ref         0.1963
_refine_ls_wR_factor_gt          0.1952
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.120
_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 0.51061(3) 0.63443(3) 0.48620(2) 0.01222(10) Uani 1 1 d . U . . .
C1 C 0.5119(6) 0.8852(4) 0.3533(4) 0.0220(12) Uani 1 1 d . U . . .
C2 C 0.5157(7) 0.9767(4) 0.3852(4) 0.0286(14) Uani 1 1 d . U . . .
H2 H 0.518420 0.985842 0.440536 0.034 Uiso 1 1 calc R U . . .
C3 C 0.5155(7) 1.0548(4) 0.3351(4) 0.0268(14) Uani 1 1 d . U . . .
N1 N 0.5191(7) 1.1462(4) 0.3669(4) 0.044(2) Uani 1 1 d . U . . .
H1A H 0.521535 1.154463 0.418139 0.053 Uiso 1 1 calc R U . . .
H1B H 0.519030 1.195429 0.335658 0.053 Uiso 1 1 calc R U . . .
C4 C 0.5200(6) 1.0411(4) 0.2552(4) 0.0249(13) Uani 1 1 d . U . . .
H4 H 0.520905 1.093489 0.220958 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5232(5) 0.9487(4) 0.2278(3) 0.0180(10) Uani 1 1 d . U . . .
C6 C 0.5196(5) 0.8716(4) 0.2762(3) 0.0204(11) Uani 1 1 d . U . . .
H6 H 0.522479 0.809443 0.256368 0.025 Uiso 1 1 calc R U . . .
C7 C 0.5111(6) 0.7996(4) 0.4065(4) 0.0202(10) Uani 1 1 d . U . . .
O1 O 0.5214(4) 0.8094(3) 0.4804(3) 0.0276(10) Uani 1 1 d . U . . .
O2 O 0.4964(4) 0.7210(3) 0.3706(3) 0.0254(10) Uani 1 1 d . U . . .
C8 C 0.5286(5) 0.9308(4) 0.1440(3) 0.0145(9) Uani 1 1 d . U . . .
O3 O 0.5446(4) 0.8465(3) 0.1250(2) 0.0167(8) Uani 1 1 d . U . . .
O4 O 0.5199(3) 0.9972(3) 0.0930(2) 0.0152(7) Uani 1 1 d . U . . .
N2 N 0.6779(4) 0.6205(3) 0.5020(3) 0.0170(8) Uani 1 1 d . U . . .
C9 C 0.7476(5) 0.6605(5) 0.5643(4) 0.0263(12) Uani 1 1 d . U . . .
H9 H 0.726260 0.687723 0.606381 0.032 Uiso 1 1 calc R U . . .
C10 C 0.8538(5) 0.6657(6) 0.5731(4) 0.0285(12) Uani 1 1 d . U . . .
H10 H 0.901931 0.690099 0.621622 0.034 Uiso 1 1 calc R U . . .
C11 C 0.8827(5) 0.6348(5) 0.5099(4) 0.0252(11) Uani 1 1 d . U . . .
C12 C 0.8127(5) 0.5909(5) 0.4443(5) 0.0275(13) Uani 1 1 d . U . . .
H12 H 0.832335 0.564330 0.401117 0.033 Uiso 1 1 calc R U . . .
C13 C 0.7107(5) 0.5866(5) 0.4432(4) 0.0227(11) Uani 1 1 d . U . . .
H13 H 0.662307 0.557590 0.397178 0.027 Uiso 1 1 calc R U . . .
C14 C 0.9895(6) 0.6415(5) 0.5089(5) 0.0315(13) Uani 1 1 d . U . . .
H14 H 1.036847 0.666320 0.557697 0.038 Uiso 1 1 calc R U . . .
C15 C 1.0284(6) 0.6187(6) 0.4514(5) 0.0321(14) Uani 1 1 d . U . . .
H15 H 0.984690 0.593687 0.401097 0.039 Uiso 1 1 calc R U . . .
C16 C 1.3076(5) 0.6789(5) 0.5259(5) 0.0291(13) Uani 1 1 d . U . . .
H16 H 1.356264 0.709318 0.570809 0.035 Uiso 1 1 calc R U . . .
N3 N 1.3376(3) 0.6390(4) 0.4681(3) 0.0157(8) Uani 1 1 d . U . . .
C17 C 1.2040(5) 0.6770(6) 0.5220(6) 0.0351(15) Uani 1 1 d . U . . .
H17 H 1.183661 0.709184 0.562479 0.042 Uiso 1 1 calc R U . . .
C18 C 1.1349(5) 0.6301(5) 0.4616(5) 0.0266(11) Uani 1 1 d . U . . .
C19 C 1.1692(5) 0.5885(5) 0.3999(4) 0.0243(11) Uani 1 1 d . U . . .
H19 H 1.122488 0.557401 0.354253 0.029 Uiso 1 1 calc R U . . .
C20 C 1.2698(5) 0.5939(5) 0.4070(4) 0.0235(11) Uani 1 1 d . U . . .
H20 H 1.292111 0.563982 0.366512 0.028 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 N2 2.263(5) . ?
Cd1 O2 2.291(4) . ?
Cd1 O3 2.297(4) 4_576 ?
Cd1 N3 2.326(4) 1_455 ?
Cd1 O4 2.332(4) 2_645 ?
Cd1 O1 2.485(4) . ?
Cd1 O4 2.591(4) 4_576 ?
C1 C6 1.380(7) . ?
C1 C2 1.402(8) . ?
C1 C7 1.521(7) . ?
C2 C3 1.402(8) . ?
C2 H2 0.9500 . ?
C3 N1 1.400(8) . ?
C3 C4 1.410(8) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
C4 C5 1.397(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(7) . ?
C5 C8 1.492(7) . ?
C6 H6 0.9500 . ?
C7 O1 1.241(7) . ?
C7 O2 1.257(7) . ?
C8 O4 1.265(6) . ?
C8 O3 1.276(6) . ?
N2 C9 1.318(8) . ?
N2 C13 1.328(8) . ?
C9 C10 1.438(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.351(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(10) . ?
C11 C14 1.495(9) . ?
C12 C13 1.416(8) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.315(10) . ?
C14 H14 0.9500 . ?
C15 C18 1.444(10) . ?
C15 H15 0.9500 . ?
C16 N3 1.324(8) . ?
C16 C17 1.422(8) . ?
C16 H16 0.9500 . ?
N3 C20 1.326(8) . ?
C17 C18 1.340(11) . ?
C17 H17 0.9500 . ?
C18 C19 1.426(10) . ?
C19 C20 1.369(9) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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
N2 Cd1 O2 86.91(19) . . ?
N2 Cd1 O3 91.70(17) . 4_576 ?
O2 Cd1 O3 140.54(14) . 4_576 ?
N2 Cd1 N3 176.49(18) . 1_455 ?
O2 Cd1 N3 94.33(19) . 1_455 ?
O3 Cd1 N3 89.43(17) 4_576 1_455 ?
N2 Cd1 O4 88.98(17) . 2_645 ?
O2 Cd1 O4 89.41(14) . 2_645 ?
O3 Cd1 O4 130.02(13) 4_576 2_645 ?
N3 Cd1 O4 87.75(18) 1_455 2_645 ?
N2 Cd1 O1 91.05(18) . . ?
O2 Cd1 O1 54.62(14) . . ?
O3 Cd1 O1 86.02(13) 4_576 . ?
N3 Cd1 O1 92.34(19) 1_455 . ?
O4 Cd1 O1 143.95(14) 2_645 . ?
N2 Cd1 O4 92.28(16) . 4_576 ?
O2 Cd1 O4 166.31(13) . 4_576 ?
O3 Cd1 O4 53.12(12) 4_576 4_576 ?
N3 Cd1 O4 85.74(16) 1_455 4_576 ?
O4 Cd1 O4 76.91(14) 2_645 4_576 ?
O1 Cd1 O4 139.07(13) . 4_576 ?
C6 C1 C2 120.0(5) . . ?
C6 C1 C7 119.1(5) . . ?
C2 C1 C7 120.5(5) . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
N1 C3 C2 119.7(5) . . ?
N1 C3 C4 120.1(5) . . ?
C2 C3 C4 120.1(5) . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C5 C4 C3 118.3(5) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C6 C5 C4 121.6(5) . . ?
C6 C5 C8 118.2(5) . . ?
C4 C5 C8 120.2(5) . . ?
C1 C6 C5 119.9(5) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O1 C7 O2 123.3(5) . . ?
O1 C7 C1 120.5(5) . . ?
O2 C7 C1 116.2(5) . . ?
O1 C7 Cd1 66.1(3) . . ?
O2 C7 Cd1 57.2(3) . . ?
C1 C7 Cd1 173.3(4) . . ?
C7 O1 Cd1 86.7(3) . . ?
C7 O2 Cd1 95.3(3) . . ?
O4 C8 O3 120.1(5) . . ?
O4 C8 C5 121.5(5) . . ?
O3 C8 C5 118.3(5) . . ?
C8 O3 Cd1 99.4(3) . 4_575 ?
C8 O4 Cd1 169.4(4) . 2_655 ?
C8 O4 Cd1 86.0(3) . 4_575 ?
Cd1 O4 Cd1 103.10(14) 2_655 4_575 ?
C9 N2 C13 115.5(6) . . ?
C9 N2 Cd1 121.1(4) . . ?
C13 N2 Cd1 122.3(4) . . ?
N2 C9 C10 124.6(6) . . ?
N2 C9 H9 117.7 . . ?
C10 C9 H9 117.7 . . ?
C11 C10 C9 117.7(6) . . ?
C11 C10 H10 121.2 . . ?
C9 C10 H10 121.2 . . ?
C10 C11 C12 119.4(6) . . ?
C10 C11 C14 123.1(7) . . ?
C12 C11 C14 117.5(6) . . ?
C11 C12 C13 118.1(6) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
N2 C13 C12 124.4(6) . . ?
N2 C13 H13 117.8 . . ?
C12 C13 H13 117.8 . . ?
C15 C14 C11 130.3(7) . . ?
C15 C14 H14 114.9 . . ?
C11 C14 H14 114.9 . . ?
C14 C15 C18 122.6(7) . . ?
C14 C15 H15 118.7 . . ?
C18 C15 H15 118.7 . . ?
N3 C16 C17 121.3(7) . . ?
N3 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 N3 C20 119.0(5) . . ?
C16 N3 Cd1 118.5(4) . 1_655 ?
C20 N3 Cd1 122.1(4) . 1_655 ?
C18 C17 C16 120.5(7) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 116.9(6) . . ?
C17 C18 C15 126.9(7) . . ?
C19 C18 C15 116.2(7) . . ?
C20 C19 C18 119.5(7) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
N3 C20 C19 122.7(6) . . ?
N3 C20 H20 118.6 . . ?
C19 C20 H20 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
C6 C1 C2 C3 7.4(12) . . . . ?
C7 C1 C2 C3 -179.5(8) . . . . ?
C1 C2 C3 N1 179.9(8) . . . . ?
C1 C2 C3 C4 -5.3(13) . . . . ?
N1 C3 C4 C5 175.7(8) . . . . ?
C2 C3 C4 C5 0.9(13) . . . . ?
C3 C4 C5 C6 1.6(12) . . . . ?
C3 C4 C5 C8 -179.7(7) . . . . ?
C2 C1 C6 C5 -5.0(12) . . . . ?
C7 C1 C6 C5 -178.2(7) . . . . ?
C4 C5 C6 C1 0.5(11) . . . . ?
C8 C5 C6 C1 -178.3(7) . . . . ?
C6 C1 C7 O1 167.8(7) . . . . ?
C2 C1 C7 O1 -5.4(12) . . . . ?
C6 C1 C7 O2 -14.3(11) . . . . ?
C2 C1 C7 O2 172.4(7) . . . . ?
O2 C7 O1 Cd1 3.6(8) . . . . ?
C1 C7 O1 Cd1 -178.8(6) . . . . ?
O1 C7 O2 Cd1 -3.9(8) . . . . ?
C1 C7 O2 Cd1 178.4(5) . . . . ?
C6 C5 C8 O4 171.4(6) . . . . ?
C4 C5 C8 O4 -7.4(10) . . . . ?
C6 C5 C8 O3 -10.1(10) . . . . ?
C4 C5 C8 O3 171.1(7) . . . . ?
O4 C8 O3 Cd1 -12.6(7) . . . 4_575 ?
C5 C8 O3 Cd1 168.9(5) . . . 4_575 ?
O3 C8 O4 Cd1 160.9(19) . . . 2_655 ?
C5 C8 O4 Cd1 -21(3) . . . 2_655 ?
O3 C8 O4 Cd1 11.0(6) . . . 4_575 ?
C5 C8 O4 Cd1 -170.5(6) . . . 4_575 ?
C13 N2 C9 C10 -2.6(10) . . . . ?
Cd1 N2 C9 C10 -171.4(6) . . . . ?
N2 C9 C10 C11 5.9(12) . . . . ?
C9 C10 C11 C12 -6.8(11) . . . . ?
C9 C10 C11 C14 176.2(7) . . . . ?
C10 C11 C12 C13 4.8(12) . . . . ?
C14 C11 C12 C13 -178.1(7) . . . . ?
C9 N2 C13 C12 0.3(10) . . . . ?
Cd1 N2 C13 C12 169.0(6) . . . . ?
C11 C12 C13 N2 -1.4(12) . . . . ?
C10 C11 C14 C15 -176.7(8) . . . . ?
C12 C11 C14 C15 6.2(13) . . . . ?
C11 C14 C15 C18 -179.8(7) . . . . ?
C17 C16 N3 C20 -2.2(11) . . . . ?
C17 C16 N3 Cd1 -174.7(6) . . . 1_655 ?
N3 C16 C17 C18 3.6(13) . . . . ?
C16 C17 C18 C19 -4.0(12) . . . . ?
C16 C17 C18 C15 177.4(8) . . . . ?
C14 C15 C18 C17 -11.1(14) . . . . ?
C14 C15 C18 C19 170.2(7) . . . . ?
C17 C18 C19 C20 3.3(11) . . . . ?
C15 C18 C19 C20 -177.9(7) . . . . ?
C16 N3 C20 C19 1.6(10) . . . . ?
Cd1 N3 C20 C19 173.7(5) 1_655 . . . ?
C18 C19 C20 N3 -2.2(11) . . . . ?

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 H1A O1 0.88 2.09 2.933(7) 160.9 3_676 yes
N1 H1B O3 0.88 2.49 2.988(7) 116.3 2_655 yes
C4 H4 O2 0.95 2.36 3.303(7) 173.7 2_655 yes
C16 H16 N1 0.95 2.67 3.530(10) 150.8 3_776 yes
C16 H16 O3 0.95 2.60 3.203(8) 121.5 4_676 yes
C20 H20 O4 0.95 2.65 3.231(8) 119.7 2_745 yes

_refine_diff_density_max         4.766
_refine_diff_density_min         -3.348
_refine_diff_density_rms         0.232



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylformamide/ethanol'
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 2207272'
loop_
_audit_author_name
_audit_author_address
'Mark Elsegood'
;Loughborough University
United Kingdom
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT043_cr478               
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..     176.26 Check 
RESPONSE: Due to Squeezed solvent.
;
_vrf_PLAT602_cr478               
;
PROBLEM: Solvent Accessible VOID(S) in Structure ........          ! Check 
RESPONSE: Sequeezed
;
_vrf_PLAT049_cr478               
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.9254 Check 
RESPONSE: Not true. Value is OK once Squeezed solvent is included.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 Mn N3 O4, 2(C4 H9 N O)'
_chemical_formula_sum            'C26 H31 Mn N5 O6'
_chemical_formula_weight         564.50

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           55
_space_group_name_H-M_alt        'P b a m'
_space_group_name_Hall           '-P 2 2ab'

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

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

_cell_length_a                   14.103(2)
_cell_length_b                   17.021(3)
_cell_length_c                   11.6095(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2786.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12884
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      30.48

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             1180
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.920
_exptl_crystal_size_mid          0.470
_exptl_crystal_size_min          0.450
_exptl_absorpt_coefficient_mu    0.521
_shelx_estimated_absorpt_T_min   0.646
_shelx_estimated_absorpt_T_max   0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_T_max  0.800
_exptl_absorpt_process_details   'SADABS v2009/1, Sheldrick, G.M., (2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26766
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.754
_diffrn_reflns_theta_max         30.569
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4437
_reflns_number_gt                3675
_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 APEX 2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0719P)²+18.1428P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4437
_refine_ls_number_parameters     188
_refine_ls_number_restraints     469
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.1011
_refine_ls_wR_factor_ref         0.2534
_refine_ls_wR_factor_gt          0.2487
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.029
_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 0.86427(6) 0.97908(4) 0.500000 0.0182(2) Uani 1 2 d S TU P A .
N1 N 0.8648(3) 0.97961(19) 0.3055(3) 0.0305(7) Uani 1 1 d D U . . .
C1 C 0.9141(14) 0.9266(9) 0.2449(8) 0.049(4) Uani 0.62(4) 1 d D U P A 1
H1 H 0.948546 0.887892 0.286526 0.058 Uiso 0.62(4) 1 calc R U P A 1
C2 C 0.9183(14) 0.9243(9) 0.1280(8) 0.050(4) Uani 0.62(4) 1 d D U P A 1
H2 H 0.957480 0.887021 0.089862 0.060 Uiso 0.62(4) 1 calc R U P A 1
C3 C 0.8632(4) 0.9786(2) 0.0639(3) 0.0350(9) Uani 1 1 d D U . . .
C4 C 0.8131(13) 1.0344(8) 0.1265(8) 0.040(3) Uani 0.62(4) 1 d D U P A 1
H4 H 0.777868 1.073916 0.087629 0.048 Uiso 0.62(4) 1 calc R U P A 1
C5 C 0.8146(13) 1.0323(8) 0.2460(8) 0.037(3) Uani 0.62(4) 1 d D U P A 1
H5 H 0.778322 1.070007 0.287266 0.044 Uiso 0.62(4) 1 calc R U P A 1
C1X C 0.882(3) 0.9142(10) 0.2452(14) 0.056(6) Uani 0.38(4) 1 d D U P A 2
H1X H 0.893607 0.867210 0.286959 0.073 Uiso 0.38(4) 1 calc R U P A 2
C2X C 0.883(3) 0.9101(9) 0.1286(13) 0.058(6) Uani 0.38(4) 1 d D U P A 2
H2X H 0.896556 0.861909 0.090923 0.070 Uiso 0.38(4) 1 calc R U P A 2
C4X C 0.848(2) 1.0476(8) 0.1255(11) 0.034(4) Uani 0.38(4) 1 d D U P A 2
H4X H 0.837120 1.095628 0.085939 0.041 Uiso 0.38(4) 1 calc R U P A 2
C5X C 0.847(2) 1.0458(8) 0.2462(11) 0.029(4) Uani 0.38(4) 1 d D U P A 2
H5X H 0.834076 1.092829 0.287311 0.035 Uiso 0.38(4) 1 calc R U P A 2
N2 N 0.3568(6) 0.8658(4) 0.5660(10) 0.050(3) Uani 0.5 1 d . U P B -1
C6 C 0.4477(6) 0.8341(4) 0.5445(8) 0.0305(17) Uani 0.5 1 d . U P B -1
C7 C 0.5290(6) 0.8813(4) 0.5422(9) 0.039(2) Uani 0.5 1 d . U P B -1
H7 H 0.526136 0.934029 0.568924 0.047 Uiso 0.5 1 calc R U P B -1
C8 C 0.6154(5) 0.8502(3) 0.500000 0.0448(18) Uani 1 2 d S TU P . .
C9 C 0.6290(5) 0.7687(3) 0.500000 0.0298(12) Uani 1 2 d S TU P B .
H9 H 0.691201 0.747302 0.500000 0.036 Uiso 1 2 calc R U P . .
C10 C 0.5502(4) 0.7197(3) 0.500000 0.0335(14) Uani 1 2 d S TU P . .
C11 C 0.4603(5) 0.7519(4) 0.5360(6) 0.0215(13) Uani 0.5 1 d . U P B -1
H11 H 0.409245 0.717623 0.554051 0.026 Uiso 0.5 1 calc R U P B -1
C12 C 0.7028(4) 0.9008(3) 0.500000 0.0289(11) Uani 1 2 d S TU P A .
O1 O 0.6946(3) 0.9747(2) 0.500000 0.0422(12) Uani 1 2 d S TU P . .
O2 O 0.7825(3) 0.8688(2) 0.500000 0.0306(9) Uani 1 2 d S TU P . .
C13 C 0.5645(4) 0.6324(3) 0.500000 0.0215(9) Uani 1 2 d S TU P B .
O3 O 0.6475(3) 0.6066(2) 0.500000 0.0264(8) Uani 1 2 d S TU P . .
O4 O 0.4931(3) 0.5873(2) 0.500000 0.0360(10) Uani 1 2 d S TU 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
Mn1 O4 2.140(4) 7_675 ?
Mn1 O3 2.176(3) 3_656 ?
Mn1 O2 2.203(4) . ?
Mn1 N1 2.258(3) 6_556 ?
Mn1 N1 2.258(3) . ?
Mn1 O1 2.394(5) . ?
Mn1 C12 2.638(6) . ?
N1 C5 1.335(9) . ?
N1 C1X 1.337(13) . ?
N1 C1 1.339(9) . ?
N1 C5X 1.343(11) . ?
C1 C2 1.360(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.419(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(10) . ?
C3 C4X 1.392(12) . ?
C3 C2X 1.415(13) . ?
C3 C3 1.483(8) 6 ?
C4 C5 1.388(10) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C1X C2X 1.355(14) . ?
C1X H1X 0.9500 . ?
C2X H2X 0.9500 . ?
C4X C5X 1.401(13) . ?
C4X H4X 0.9500 . ?
C5X H5X 0.9500 . ?
N2 C6 1.413(10) . ?
C6 C7 1.400(11) . ?
C6 C11 1.414(9) . ?
C7 C8 1.417(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.400(7) . ?
C8 C12 1.504(9) . ?
C9 C10 1.390(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.444(9) . ?
C10 C13 1.499(7) . ?
C11 H11 0.9500 . ?
C12 O2 1.249(7) . ?
C12 O1 1.264(6) . ?
C13 O3 1.250(7) . ?
C13 O4 1.266(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Mn1 O3 126.26(16) 7_675 3_656 ?
O4 Mn1 O2 89.67(16) 7_675 . ?
O3 Mn1 O2 144.07(17) 3_656 . ?
O4 Mn1 N1 89.97(10) 7_675 6_556 ?
O3 Mn1 N1 89.79(9) 3_656 6_556 ?
O2 Mn1 N1 90.29(9) . 6_556 ?
O4 Mn1 N1 89.97(10) 7_675 . ?
O3 Mn1 N1 89.79(9) 3_656 . ?
O2 Mn1 N1 90.29(9) . . ?
N1 Mn1 N1 179.4(2) 6_556 . ?
O4 Mn1 O1 146.33(15) 7_675 . ?
O3 Mn1 O1 87.41(15) 3_656 . ?
O2 Mn1 O1 56.67(15) . . ?
N1 Mn1 O1 90.18(11) 6_556 . ?
N1 Mn1 O1 90.18(11) . . ?
O4 Mn1 C12 117.76(17) 7_675 . ?
O3 Mn1 C12 115.98(17) 3_656 . ?
O2 Mn1 C12 28.09(16) . . ?
N1 Mn1 C12 90.27(10) 6_556 . ?
N1 Mn1 C12 90.27(10) . . ?
O1 Mn1 C12 28.57(15) . . ?
C5 N1 C1 117.2(7) . . ?
C1X N1 C5X 117.6(10) . . ?
C5 N1 Mn1 121.2(5) . . ?
C1X N1 Mn1 121.4(8) . . ?
C1 N1 Mn1 121.6(5) . . ?
C5X N1 Mn1 121.0(6) . . ?
N1 C1 C2 124.5(9) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C1 C2 C3 118.7(9) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4X C3 C2X 116.9(9) . . ?
C4 C3 C2 116.7(6) . . ?
C4 C3 C3 121.6(4) . 6 ?
C2 C3 C3 121.6(4) . 6 ?
C5 C4 C3 119.9(8) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C5 C4 122.8(9) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
N1 C1X C2X 124.6(14) . . ?
N1 C1X H1X 117.7 . . ?
C2X C1X H1X 117.7 . . ?
C1X C2X C3 119.1(13) . . ?
C1X C2X H2X 120.4 . . ?
C3 C2X H2X 120.4 . . ?
C3 C4X C5X 119.8(12) . . ?
C3 C4X H4X 120.1 . . ?
C5X C4X H4X 120.1 . . ?
N1 C5X C4X 122.0(12) . . ?
N1 C5X H5X 119.0 . . ?
C4X C5X H5X 119.0 . . ?
C7 C6 N2 121.7(6) . . ?
C7 C6 C11 117.6(7) . . ?
N2 C6 C11 120.3(7) . . ?
C6 C7 C8 119.8(7) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 119.2(6) . . ?
C9 C8 C12 117.0(6) . . ?
C7 C8 C12 119.5(5) . . ?
C10 C9 C8 119.0(6) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 118.3(5) . . ?
C9 C10 C13 119.2(5) . . ?
C11 C10 C13 119.6(5) . . ?
C6 C11 C10 120.4(6) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
O2 C12 O1 121.1(6) . . ?
O2 C12 C8 119.2(5) . . ?
O1 C12 C8 119.6(6) . . ?
O2 C12 Mn1 56.2(3) . . ?
O1 C12 Mn1 64.9(3) . . ?
C8 C12 Mn1 175.4(4) . . ?
C12 O1 Mn1 86.5(4) . . ?
C12 O2 Mn1 95.7(3) . . ?
O3 C13 O4 122.1(5) . . ?
O3 C13 C10 118.3(5) . . ?
O4 C13 C10 119.6(5) . . ?
C13 O3 Mn1 106.3(3) . 3_646 ?
C13 O4 Mn1 174.6(4) . 7_575 ?

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
C5 N1 C1 C2 1.8(19) . . . . ?
Mn1 N1 C1 C2 -179.1(11) . . . . ?
N1 C1 C2 C3 -4(2) . . . . ?
C1 C2 C3 C4 4.3(16) . . . . ?
C1 C2 C3 C3 -179.0(10) . . . 6 ?
C2 C3 C4 C5 -3.5(15) . . . . ?
C3 C3 C4 C5 179.8(8) 6 . . . ?
C1 N1 C5 C4 -0.9(15) . . . . ?
Mn1 N1 C5 C4 -179.9(8) . . . . ?
C3 C4 C5 N1 1.9(17) . . . . ?
C5X N1 C1X C2X 0(4) . . . . ?
Mn1 N1 C1X C2X 180(2) . . . . ?
N1 C1X C2X C3 -1(4) . . . . ?
C4X C3 C2X C1X 3(3) . . . . ?
C3 C3 C2X C1X 180.0(19) 6 . . . ?
C2X C3 C4X C5X -3(2) . . . . ?
C3 C3 C4X C5X 179.5(12) 6 . . . ?
C1X N1 C5X C4X -1(2) . . . . ?
Mn1 N1 C5X C4X 179.7(12) . . . . ?
C3 C4X C5X N1 2(2) . . . . ?
N2 C6 C7 C8 -168.5(9) . . . . ?
C11 C6 C7 C8 17.7(13) . . . . ?
C6 C7 C8 C9 -22.7(11) . . . . ?
C6 C7 C8 C12 -178.8(7) . . . . ?
C7 C8 C9 C10 23.4(5) . . . . ?
C12 C8 C9 C10 180.0 . . . . ?
C8 C9 C10 C11 -19.2(3) . . . . ?
C8 C9 C10 C13 180.0 . . . . ?
C7 C6 C11 C10 -13.8(12) . . . . ?
N2 C6 C11 C10 172.3(8) . . . . ?
C9 C10 C11 C6 14.7(8) . . . . ?
C13 C10 C11 C6 175.4(6) . . . . ?
C9 C8 C12 O2 0.0 . . . . ?
C7 C8 C12 O2 156.6(5) . . . . ?
C9 C8 C12 O1 180.0 . . . . ?
C7 C8 C12 O1 -23.4(5) . . . . ?
O2 C12 O1 Mn1 0.0 . . . . ?
C8 C12 O1 Mn1 180.0 . . . . ?
O1 C12 O2 Mn1 0.0 . . . . ?
C8 C12 O2 Mn1 180.0 . . . . ?
C9 C10 C13 O3 0.0 . . . . ?
C11 C10 C13 O3 -160.6(4) . . . . ?
C9 C10 C13 O4 180.0 . . . . ?
C11 C10 C13 O4 19.4(4) . . . . ?
O4 C13 O3 Mn1 0.0 . . . 3_646 ?
C10 C13 O3 Mn1 180.0 . . . 3_646 ?

_refine_diff_density_max         1.658
_refine_diff_density_min         -1.249
_refine_diff_density_rms         0.133


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylacetamide/ethanol'
