# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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 1905204'
loop_
_audit_author_name
_audit_author_address
'Liming Fan'
;North University of China
China
;
_audit_update_record             
;
2019-03-24 deposited with the CCDC.	2019-07-30 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         'C34 H20 Mn N2 O8'
_chemical_formula_sum            'C34 H20 Mn N2 O8'
_chemical_formula_weight         639.46

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   12.166(4)
_cell_length_b                   17.6501(10)
_cell_length_c                   14.104(7)
_cell_angle_alpha                90
_cell_angle_beta                 114.646(11)
_cell_angle_gamma                90
_cell_volume                     2752.7(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1977
_cell_measurement_theta_min      3.6780
_cell_measurement_theta_max      26.0070

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             1308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.541
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95040
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11939
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.967
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3131
_reflns_number_gt                2182
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0866P)²+6.4520P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         3131
_refine_ls_number_parameters     258
_refine_ls_number_restraints     278
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.1846
_refine_ls_wR_factor_gt          0.1619
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.021
_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 0.250000 0.69313(4) 0.500000 0.0263(3) Uani 1 2 d S T P . .
O3 O 0.4290(2) 0.70605(14) 0.6146(2) 0.0349(7) Uani 1 1 d . . . . .
O4 O 0.4478(2) 0.83138(16) 0.6361(3) 0.0487(8) Uani 1 1 d . . . . .
O2 O 1.1814(3) 0.75981(16) 0.6018(2) 0.0426(7) Uani 1 1 d . . . . .
O1 O 1.2453(3) 0.87830(16) 0.6118(3) 0.0454(8) Uani 1 1 d D . . . .
C6 C 0.8924(3) 0.83899(18) 0.6601(3) 0.0223(7) Uani 1 1 d D . . . .
N1 N 0.195(2) 0.5882(7) 0.5641(15) 0.039(2) Uani 0.5 1 d G U P A -1
C22 C 0.2247(19) 0.5206(9) 0.5301(14) 0.040(2) Uani 0.5 1 d G U P A -1
C18 C 0.1933(13) 0.4519(7) 0.5600(12) 0.047(2) Uani 0.5 1 d G U P A -1
C19 C 0.1320(9) 0.4508(6) 0.6241(10) 0.050(3) Uani 0.5 1 d G U P A -1
H19 H 0.111004 0.404763 0.644117 0.060 Uiso 0.5 1 calc R U P A -1
C20 C 0.1023(11) 0.5184(7) 0.6581(9) 0.052(3) Uani 0.5 1 d G U P A -1
H20 H 0.061295 0.517640 0.700971 0.062 Uiso 0.5 1 calc R U P A -1
C21 C 0.1337(17) 0.5871(6) 0.6282(12) 0.047(3) Uani 0.5 1 d G U P A -1
H21 H 0.113793 0.632376 0.650955 0.056 Uiso 0.5 1 calc R U P A -1
C9 C 0.6936(3) 0.7989(2) 0.6683(3) 0.0260(8) Uani 1 1 d . . . . .
H9 H 0.654813 0.832049 0.613034 0.031 Uiso 1 1 calc R U . . .
C10 C 0.6241(3) 0.75781(19) 0.7066(3) 0.0258(8) Uani 1 1 d . . . . .
C11 C 0.4890(3) 0.7659(2) 0.6491(3) 0.0283(8) Uani 1 1 d . . . . .
C8 C 0.8199(3) 0.79286(19) 0.7092(3) 0.0250(7) Uani 1 1 d D . . . .
C2 C 1.0596(3) 0.8586(2) 0.6214(3) 0.0317(8) Uani 1 1 d . . . . .
C1 C 1.1673(3) 0.8276(2) 0.6108(3) 0.0311(8) Uani 1 1 d . . . . .
C7 C 0.9867(4) 0.8117(2) 0.6515(3) 0.0317(8) Uani 1 1 d . . . . .
H7 H 1.006215 0.760782 0.665387 0.038 Uiso 1 1 calc R U . . .
C5 C 0.8568(4) 0.9152(2) 0.6380(3) 0.0381(9) Uani 1 1 d . . . . .
H5 H 0.787974 0.933182 0.643742 0.046 Uiso 1 1 calc R U . . .
C3 C 1.0307(4) 0.9351(2) 0.6020(3) 0.0409(10) Uani 1 1 d . . . . .
H3 H 1.080423 0.967484 0.585374 0.049 Uiso 1 1 calc R U . . .
C4 C 0.9263(4) 0.9625(2) 0.6078(4) 0.0456(11) Uani 1 1 d . . . . .
H4 H 0.903561 1.012764 0.591311 0.055 Uiso 1 1 calc R U . . .
C17 C 0.2404(12) 0.3816(7) 0.5332(11) 0.053(3) Uani 0.5 1 d . U P A -1
H17 H 0.224754 0.334804 0.555436 0.063 Uiso 0.5 1 calc R U P A -1
C16 C 0.3056(10) 0.3856(7) 0.4767(12) 0.052(3) Uani 0.5 1 d . U P A -1
H16 H 0.335549 0.340623 0.462374 0.063 Uiso 0.5 1 calc R U P A -1
N2 N 0.312(2) 0.5917(8) 0.4379(15) 0.038(2) Uani 0.5 1 d . U P A -1
C12 C 0.3767(18) 0.5947(8) 0.3859(13) 0.045(3) Uani 0.5 1 d . U P A -1
H12 H 0.392058 0.641994 0.365053 0.054 Uiso 0.5 1 calc R U P A -1
C13 C 0.4265(12) 0.5299(8) 0.3581(10) 0.049(2) Uani 0.5 1 d . U P A -1
H13 H 0.474739 0.535765 0.321967 0.058 Uiso 0.5 1 calc R U P A -1
C14 C 0.4047(11) 0.4631(7) 0.3829(10) 0.047(2) Uani 0.5 1 d . U P A -1
H14 H 0.437285 0.420844 0.364581 0.056 Uiso 0.5 1 calc R U P A -1
C15 C 0.3319(15) 0.4538(9) 0.4374(14) 0.049(2) Uani 0.5 1 d . U P A -1
C23 C 0.290(2) 0.5235(10) 0.4647(15) 0.040(2) Uani 0.5 1 d . U P A -1
H1 H 1.309(3) 0.855(2) 0.614(4) 0.059 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
Mn1 O3 2.114(3) . ?
Mn1 O3 2.114(3) 2_556 ?
Mn1 N2 2.258(12) . ?
Mn1 O2 2.268(3) 1_455 ?
Mn1 O2 2.268(3) 2_656 ?
Mn1 N1 2.280(11) . ?
O3 C11 1.261(4) . ?
O4 C11 1.243(4) . ?
O2 C1 1.223(5) . ?
O1 C1 1.300(5) . ?
O1 H1 0.861(10) . ?
C6 C7 1.296(5) . ?
C6 C5 1.408(5) . ?
C6 C8 1.558(4) . ?
N1 C22 1.3900 . ?
N1 C21 1.3900 . ?
C22 C18 1.3900 . ?
C22 C23 1.451(11) . ?
C18 C19 1.3900 . ?
C18 C17 1.481(16) . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 C21 1.3900 . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C9 C10 1.383(5) . ?
C9 C8 1.403(5) . ?
C9 H9 0.9300 . ?
C10 C8 1.414(5) 7_666 ?
C10 C11 1.506(5) . ?
C2 C3 1.394(5) . ?
C2 C7 1.402(5) . ?
C2 C1 1.484(5) . ?
C7 H7 0.9300 . ?
C5 C4 1.376(6) . ?
C5 H5 0.9300 . ?
C3 C4 1.393(6) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C17 C16 1.340(15) . ?
C17 H17 0.9300 . ?
C16 C15 1.42(2) . ?
C16 H16 0.9300 . ?
N2 C12 1.279(13) . ?
N2 C23 1.322(11) . ?
C12 C13 1.423(13) . ?
C12 H12 0.9300 . ?
C13 C14 1.288(15) . ?
C13 H13 0.9300 . ?
C14 C15 1.404(17) . ?
C14 H14 0.9300 . ?
C15 C23 1.441(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
O3 Mn1 O3 167.62(14) . 2_556 ?
O3 Mn1 N2 88.7(6) . . ?
O3 Mn1 N2 101.2(6) 2_556 . ?
O3 Mn1 O2 89.63(11) . 1_455 ?
O3 Mn1 O2 83.95(11) 2_556 1_455 ?
N2 Mn1 O2 158.2(5) . 1_455 ?
O3 Mn1 O2 83.95(11) . 2_656 ?
O3 Mn1 O2 89.63(11) 2_556 2_656 ?
N2 Mn1 O2 83.9(5) . 2_656 ?
O2 Mn1 O2 117.49(15) 1_455 2_656 ?
O3 Mn1 N1 99.4(6) . . ?
O3 Mn1 N1 90.7(6) 2_556 . ?
N2 Mn1 N1 73.2(2) . . ?
O2 Mn1 N1 85.6(5) 1_455 . ?
O2 Mn1 N1 156.8(5) 2_656 . ?
C11 O3 Mn1 129.2(2) . . ?
C1 O2 Mn1 132.6(3) . 1_655 ?
C1 O1 H1 108(3) . . ?
C7 C6 C5 122.5(3) . . ?
C7 C6 C8 122.3(3) . . ?
C5 C6 C8 114.8(3) . . ?
C22 N1 C21 120.0 . . ?
C22 N1 Mn1 113.5(8) . . ?
C21 N1 Mn1 126.5(8) . . ?
C18 C22 N1 120.0 . . ?
C18 C22 C23 121.2(17) . . ?
N1 C22 C23 118.8(17) . . ?
C22 C18 C19 120.0 . . ?
C22 C18 C17 118.0(10) . . ?
C19 C18 C17 121.6(10) . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.0 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 N1 120.0 . . ?
C20 C21 H21 120.0 . . ?
N1 C21 H21 120.0 . . ?
C10 C9 C8 122.8(3) . . ?
C10 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
C9 C10 C8 120.1(3) . 7_666 ?
C9 C10 C11 116.6(3) . . ?
C8 C10 C11 123.2(3) 7_666 . ?
O4 C11 O3 126.1(3) . . ?
O4 C11 C10 116.7(3) . . ?
O3 C11 C10 117.1(3) . . ?
C9 C8 C10 117.1(3) . 7_666 ?
C9 C8 C6 120.2(3) . . ?
C10 C8 C6 122.7(3) 7_666 . ?
C3 C2 C7 119.5(4) . . ?
C3 C2 C1 119.9(4) . . ?
C7 C2 C1 120.6(3) . . ?
O2 C1 O1 122.9(4) . . ?
O2 C1 C2 122.6(4) . . ?
O1 C1 C2 114.6(3) . . ?
C6 C7 C2 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
C4 C5 C6 118.4(4) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C16 C17 C18 119.7(14) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C16 C15 124.3(15) . . ?
C17 C16 H16 117.8 . . ?
C15 C16 H16 117.8 . . ?
C12 N2 C23 116.5(8) . . ?
C12 N2 Mn1 125.1(11) . . ?
C23 N2 Mn1 118.1(10) . . ?
N2 C12 C13 123.9(10) . . ?
N2 C12 H12 118.0 . . ?
C13 C12 H12 118.0 . . ?
C14 C13 C12 120.1(11) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.2(10) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 127.6(12) . . ?
C14 C15 C23 114.7(10) . . ?
C16 C15 C23 117.3(13) . . ?
N2 C23 C15 124.5(10) . . ?
N2 C23 C22 116.3(18) . . ?
C15 C23 C22 119.1(18) . . ?

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
C21 N1 C22 C18 0.0 . . . . ?
Mn1 N1 C22 C18 -177.9(12) . . . . ?
C21 N1 C22 C23 -179.0(7) . . . . ?
Mn1 N1 C22 C23 3.0(9) . . . . ?
N1 C22 C18 C19 0.0 . . . . ?
C23 C22 C18 C19 179.0(7) . . . . ?
N1 C22 C18 C17 -172.3(11) . . . . ?
C23 C22 C18 C17 6.7(10) . . . . ?
C22 C18 C19 C20 0.0 . . . . ?
C17 C18 C19 C20 172.0(11) . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 N1 0.0 . . . . ?
C22 N1 C21 C20 0.0 . . . . ?
Mn1 N1 C21 C20 177.6(13) . . . . ?
C8 C9 C10 C8 0.2(6) . . . 7_666 ?
C8 C9 C10 C11 -175.3(3) . . . . ?
Mn1 O3 C11 O4 14.0(6) . . . . ?
Mn1 O3 C11 C10 -162.6(2) . . . . ?
C9 C10 C11 O4 -53.8(5) . . . . ?
C8 C10 C11 O4 130.9(4) 7_666 . . . ?
C9 C10 C11 O3 123.2(4) . . . . ?
C8 C10 C11 O3 -52.2(5) 7_666 . . . ?
C10 C9 C8 C10 -0.2(6) . . . 7_666 ?
C10 C9 C8 C6 178.1(3) . . . . ?
C7 C6 C8 C9 -142.9(4) . . . . ?
C5 C6 C8 C9 44.7(5) . . . . ?
C7 C6 C8 C10 35.3(5) . . . 7_666 ?
C5 C6 C8 C10 -137.1(4) . . . 7_666 ?
Mn1 O2 C1 O1 -41.6(6) 1_655 . . . ?
Mn1 O2 C1 C2 138.5(3) 1_655 . . . ?
C3 C2 C1 O2 -161.9(4) . . . . ?
C7 C2 C1 O2 18.5(6) . . . . ?
C3 C2 C1 O1 18.2(6) . . . . ?
C7 C2 C1 O1 -161.5(4) . . . . ?
C5 C6 C7 C2 1.4(6) . . . . ?
C8 C6 C7 C2 -170.5(3) . . . . ?
C3 C2 C7 C6 0.8(6) . . . . ?
C1 C2 C7 C6 -179.6(4) . . . . ?
C7 C6 C5 C4 -1.0(6) . . . . ?
C8 C6 C5 C4 171.4(4) . . . . ?
C7 C2 C3 C4 -3.2(6) . . . . ?
C1 C2 C3 C4 177.2(4) . . . . ?
C6 C5 C4 C3 -1.5(7) . . . . ?
C2 C3 C4 C5 3.6(7) . . . . ?
C22 C18 C17 C16 -3.6(14) . . . . ?
C19 C18 C17 C16 -175.8(9) . . . . ?
C18 C17 C16 C15 -1.4(16) . . . . ?
C23 N2 C12 C13 -1.2(14) . . . . ?
Mn1 N2 C12 C13 172.4(14) . . . . ?
N2 C12 C13 C14 1.9(17) . . . . ?
C12 C13 C14 C15 0.0(16) . . . . ?
C13 C14 C15 C16 -175.4(13) . . . . ?
C13 C14 C15 C23 -2.2(15) . . . . ?
C17 C16 C15 C14 176.2(12) . . . . ?
C17 C16 C15 C23 3.2(17) . . . . ?
C12 N2 C23 C15 -1.4(14) . . . . ?
Mn1 N2 C23 C15 -175.4(14) . . . . ?
C12 N2 C23 C22 175.6(9) . . . . ?
Mn1 N2 C23 C22 1.6(13) . . . . ?
C14 C15 C23 N2 3.1(14) . . . . ?
C16 C15 C23 N2 177.0(13) . . . . ?
C14 C15 C23 C22 -173.9(9) . . . . ?
C16 C15 C23 C22 0.0(14) . . . . ?
C18 C22 C23 N2 177.8(7) . . . . ?
N1 C22 C23 N2 -3.2(9) . . . . ?
C18 C22 C23 C15 -5.0(9) . . . . ?
N1 C22 C23 C15 174.0(8) . . . . ?

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
O1 H1 O4 0.861(10) 1.643(17) 2.484(4) 165(5) 1_655 yes

_refine_diff_density_max         1.332
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.084


_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1938458'
loop_
_audit_author_name
_audit_author_address
'Liming Fan'
;North University of China
China
;
_audit_update_record             
;
2019-07-04 deposited with the CCDC.	2019-07-30 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         'C23 H13 Cu N2 O4'
_chemical_formula_sum            'C23 H13 Cu N2 O4'
_chemical_formula_weight         444.89

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.280(5)
_cell_length_b                   10.104(5)
_cell_length_c                   10.836(6)
_cell_angle_alpha                67.98(2)
_cell_angle_beta                 76.875(19)
_cell_angle_gamma                67.945(15)
_cell_volume                     868.7(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9854
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.059
_exptl_absorpt_coefficient_mu    1.294
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30894
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.974
_diffrn_reflns_theta_max         27.598
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4037
_reflns_number_gt                3511
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4017
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1315
_refine_ls_wR_factor_gt          0.1252
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
Cu1 Cu 0.41578(3) 0.04131(3) 0.32601(3) 0.02247(14) Uani 1 1 d . . . . .
O1 O 0.7491(2) 0.8332(2) 0.58325(19) 0.0297(4) Uani 1 1 d . . . . .
O2 O 0.5364(2) 0.1794(2) 0.50342(17) 0.0287(4) Uani 1 1 d . . . . .
O3 O 0.5800(2) 0.1181(2) 0.31745(19) 0.0317(4) Uani 1 1 d . . . . .
O4 O 0.7338(3) 0.6396(2) 0.7649(2) 0.0439(5) Uani 1 1 d . . . . .
N1 N 0.2598(2) -0.0344(2) 0.2887(2) 0.0238(4) Uani 1 1 d . . . . .
N2 N 0.5544(2) -0.0677(2) 0.1974(2) 0.0235(4) Uani 1 1 d . . . . .
C1 C 0.3286(3) -0.1347(3) 0.2220(2) 0.0233(5) Uani 1 1 d . . . . .
C2 C 0.4887(3) -0.1485(3) 0.1669(2) 0.0231(5) Uani 1 1 d . . . . .
C3 C 0.5630(3) -0.2364(3) 0.0838(3) 0.0277(5) Uani 1 1 d . . . . .
C4 C 0.4842(4) -0.3234(3) 0.0643(3) 0.0379(7) Uani 1 1 d . . . . .
H5 H 0.5339 -0.3838 0.0101 0.046 Uiso 1 1 calc R U . . .
C5 C 0.3381(4) -0.3188(3) 0.1238(3) 0.0380(7) Uani 1 1 d . . . . .
H4 H 0.2913 -0.3806 0.1139 0.046 Uiso 1 1 calc R U . . .
C6 C 0.2547(3) -0.2210(3) 0.2012(3) 0.0286(5) Uani 1 1 d . . . . .
C7 C 0.0977(3) -0.2003(3) 0.2573(3) 0.0354(6) Uani 1 1 d . . . . .
H1 H 0.0433 -0.2574 0.2498 0.043 Uiso 1 1 calc R U . . .
C8 C 0.0263(3) -0.0962(3) 0.3224(3) 0.0349(6) Uani 1 1 d . . . . .
H2 H -0.0778 -0.0799 0.3574 0.042 Uiso 1 1 calc R U . . .
C9 C 0.1108(3) -0.0142(3) 0.3360(3) 0.0319(6) Uani 1 1 d . . . . .
H3 H 0.0608 0.0571 0.3799 0.038 Uiso 1 1 calc R U . . .
C10 C 0.7142(3) -0.2338(3) 0.0245(3) 0.0343(6) Uani 1 1 d . . . . .
H6 H 0.7683 -0.2879 -0.0342 0.041 Uiso 1 1 calc R U . . .
C11 C 0.7799(3) -0.1508(3) 0.0544(3) 0.0337(6) Uani 1 1 d . . . . .
H8 H 0.8791 -0.1476 0.0152 0.040 Uiso 1 1 calc R U . . .
C12 C 0.6993(3) -0.0706(3) 0.1433(3) 0.0298(5) Uani 1 1 d . . . . .
H7 H 0.7478 -0.0181 0.1653 0.036 Uiso 1 1 calc R U . . .
C13 C 0.5972(3) 0.1854(3) 0.3896(2) 0.0226(5) Uani 1 1 d . . . . .
C14 C 0.7075(3) 0.2750(3) 0.3239(2) 0.0216(5) Uani 1 1 d . . . . .
C15 C 0.7607(3) 0.3313(3) 0.3974(2) 0.0213(5) Uani 1 1 d . . . . .
H9 H 0.7209 0.3208 0.4862 0.026 Uiso 1 1 calc R U . . .
C16 C 0.8728(3) 0.4031(3) 0.3398(2) 0.0216(5) Uani 1 1 d . . . . .
C17 C 0.9253(3) 0.4244(3) 0.2058(3) 0.0297(5) Uani 1 1 d . . . . .
H12 H 0.9987 0.4742 0.1656 0.036 Uiso 1 1 calc R U . . .
C18 C 0.8698(3) 0.3723(3) 0.1311(3) 0.0331(6) Uani 1 1 d . . . . .
H10 H 0.9045 0.3883 0.0408 0.040 Uiso 1 1 calc R U . . .
C19 C 0.7630(3) 0.2967(3) 0.1908(3) 0.0293(5) Uani 1 1 d . . . . .
H11 H 0.7276 0.2596 0.1409 0.035 Uiso 1 1 calc R U . . .
C20 C 0.9388(3) 0.4550(3) 0.4204(2) 0.0210(5) Uani 1 1 d . . . . .
C21 C 0.8415(3) 0.5465(3) 0.4947(3) 0.0239(5) Uani 1 1 d . . . . .
H13 H 0.7341 0.5784 0.4913 0.029 Uiso 1 1 calc R U . . .
C22 C 0.8986(3) 0.5921(3) 0.5739(2) 0.0216(5) Uani 1 1 d . . . . .
C23 C 0.7860(3) 0.6928(3) 0.6495(3) 0.0261(5) 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
Cu1 O3 1.9243(19) . ?
Cu1 O1 1.9262(18) 2_666 ?
Cu1 N2 2.021(2) . ?
Cu1 N1 2.043(2) . ?
Cu1 O2 2.264(2) 2_656 ?
O1 C23 1.276(3) . ?
O1 Cu1 1.9262(18) 2_666 ?
O2 C13 1.223(3) . ?
O2 Cu1 2.264(2) 2_656 ?
O3 C13 1.279(3) . ?
O4 C23 1.226(3) . ?
N1 C9 1.327(3) . ?
N1 C1 1.345(3) . ?
N2 C12 1.333(3) . ?
N2 C2 1.347(3) . ?
C1 C6 1.395(3) . ?
C1 C2 1.446(3) . ?
C2 C3 1.389(3) . ?
C3 C10 1.410(4) . ?
C3 C4 1.430(4) . ?
C4 C5 1.355(4) . ?
C4 H5 0.9300 . ?
C5 C6 1.425(4) . ?
C5 H4 0.9300 . ?
C6 C7 1.415(4) . ?
C7 C8 1.366(4) . ?
C7 H1 0.9300 . ?
C8 C9 1.399(4) . ?
C8 H2 0.9300 . ?
C9 H3 0.9300 . ?
C10 C11 1.362(4) . ?
C10 H6 0.9300 . ?
C11 C12 1.395(4) . ?
C11 H8 0.9300 . ?
C12 H7 0.9300 . ?
C13 C14 1.502(3) . ?
C14 C19 1.379(4) . ?
C14 C15 1.390(3) . ?
C15 C16 1.389(3) . ?
C15 H9 0.9300 . ?
C16 C17 1.384(4) . ?
C16 C20 1.497(3) . ?
C17 C18 1.383(4) . ?
C17 H12 0.9300 . ?
C18 C19 1.375(4) . ?
C18 H10 0.9300 . ?
C19 H11 0.9300 . ?
C20 C21 1.385(3) . ?
C20 C22 1.410(3) 2_766 ?
C21 C22 1.385(3) . ?
C21 H13 0.9300 . ?
C22 C20 1.410(3) 2_766 ?
C22 C23 1.496(3) . ?

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 Cu1 O1 98.46(8) . 2_666 ?
O3 Cu1 N2 88.48(9) . . ?
O1 Cu1 N2 166.65(8) 2_666 . ?
O3 Cu1 N1 166.46(8) . . ?
O1 Cu1 N1 90.85(9) 2_666 . ?
N2 Cu1 N1 80.52(9) . . ?
O3 Cu1 O2 105.00(8) . 2_656 ?
O1 Cu1 O2 99.01(8) 2_666 2_656 ?
N2 Cu1 O2 90.10(9) . 2_656 ?
N1 Cu1 O2 83.04(8) . 2_656 ?
C23 O1 Cu1 113.80(17) . 2_666 ?
C13 O2 Cu1 121.36(16) . 2_656 ?
C13 O3 Cu1 130.71(16) . . ?
C9 N1 C1 117.9(2) . . ?
C9 N1 Cu1 128.93(19) . . ?
C1 N1 Cu1 112.45(16) . . ?
C12 N2 C2 118.0(2) . . ?
C12 N2 Cu1 128.31(18) . . ?
C2 N2 Cu1 113.66(17) . . ?
N1 C1 C6 124.5(2) . . ?
N1 C1 C2 116.2(2) . . ?
C6 C1 C2 119.3(2) . . ?
N2 C2 C3 124.2(2) . . ?
N2 C2 C1 115.8(2) . . ?
C3 C2 C1 120.0(2) . . ?
C2 C3 C10 116.7(2) . . ?
C2 C3 C4 119.1(3) . . ?
C10 C3 C4 124.2(2) . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H5 119.6 . . ?
C3 C4 H5 119.6 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H4 119.4 . . ?
C6 C5 H4 119.4 . . ?
C1 C6 C7 116.0(2) . . ?
C1 C6 C5 119.2(2) . . ?
C7 C6 C5 124.7(2) . . ?
C8 C7 C6 119.7(2) . . ?
C8 C7 H1 120.2 . . ?
C6 C7 H1 120.2 . . ?
C7 C8 C9 119.5(3) . . ?
C7 C8 H2 120.2 . . ?
C9 C8 H2 120.2 . . ?
N1 C9 C8 122.4(3) . . ?
N1 C9 H3 118.8 . . ?
C8 C9 H3 118.8 . . ?
C11 C10 C3 119.0(2) . . ?
C11 C10 H6 120.5 . . ?
C3 C10 H6 120.5 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H8 119.7 . . ?
C12 C11 H8 119.7 . . ?
N2 C12 C11 121.5(2) . . ?
N2 C12 H7 119.3 . . ?
C11 C12 H7 119.3 . . ?
O2 C13 O3 126.3(2) . . ?
O2 C13 C14 119.8(2) . . ?
O3 C13 C14 113.9(2) . . ?
C19 C14 C15 119.0(2) . . ?
C19 C14 C13 120.3(2) . . ?
C15 C14 C13 120.6(2) . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H9 119.6 . . ?
C14 C15 H9 119.6 . . ?
C17 C16 C15 118.9(2) . . ?
C17 C16 C20 119.9(2) . . ?
C15 C16 C20 121.2(2) . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 H12 119.7 . . ?
C16 C17 H12 119.7 . . ?
C19 C18 C17 119.7(2) . . ?
C19 C18 H10 120.1 . . ?
C17 C18 H10 120.1 . . ?
C18 C19 C14 120.9(2) . . ?
C18 C19 H11 119.6 . . ?
C14 C19 H11 119.6 . . ?
C21 C20 C22 118.3(2) . 2_766 ?
C21 C20 C16 120.9(2) . . ?
C22 C20 C16 120.8(2) 2_766 . ?
C22 C21 C20 122.2(2) . . ?
C22 C21 H13 118.9 . . ?
C20 C21 H13 118.9 . . ?
C21 C22 C20 119.4(2) . 2_766 ?
C21 C22 C23 119.0(2) . . ?
C20 C22 C23 121.6(2) 2_766 . ?
O4 C23 O1 124.8(2) . . ?
O4 C23 C22 120.6(2) . . ?
O1 C23 C22 114.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C6 -1.1(4) . . . . ?
Cu1 N1 C1 C6 169.9(2) . . . . ?
C9 N1 C1 C2 177.3(2) . . . . ?
Cu1 N1 C1 C2 -11.6(3) . . . . ?
C12 N2 C2 C3 0.9(4) . . . . ?
Cu1 N2 C2 C3 -178.0(2) . . . . ?
C12 N2 C2 C1 -176.6(2) . . . . ?
Cu1 N2 C2 C1 4.5(3) . . . . ?
N1 C1 C2 N2 4.9(3) . . . . ?
C6 C1 C2 N2 -176.5(2) . . . . ?
N1 C1 C2 C3 -172.7(2) . . . . ?
C6 C1 C2 C3 5.9(4) . . . . ?
N2 C2 C3 C10 -2.8(4) . . . . ?
C1 C2 C3 C10 174.6(2) . . . . ?
N2 C2 C3 C4 176.8(2) . . . . ?
C1 C2 C3 C4 -5.8(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C10 C3 C4 C5 -179.3(3) . . . . ?
C3 C4 C5 C6 3.7(4) . . . . ?
N1 C1 C6 C7 -1.1(4) . . . . ?
C2 C1 C6 C7 -179.5(2) . . . . ?
N1 C1 C6 C5 177.2(2) . . . . ?
C2 C1 C6 C5 -1.2(4) . . . . ?
C4 C5 C6 C1 -3.6(4) . . . . ?
C4 C5 C6 C7 174.6(3) . . . . ?
C1 C6 C7 C8 2.5(4) . . . . ?
C5 C6 C7 C8 -175.7(3) . . . . ?
C6 C7 C8 C9 -1.8(4) . . . . ?
C1 N1 C9 C8 2.0(4) . . . . ?
Cu1 N1 C9 C8 -167.4(2) . . . . ?
C7 C8 C9 N1 -0.6(4) . . . . ?
C2 C3 C10 C11 2.0(4) . . . . ?
C4 C3 C10 C11 -177.6(3) . . . . ?
C3 C10 C11 C12 0.6(4) . . . . ?
C2 N2 C12 C11 1.9(4) . . . . ?
Cu1 N2 C12 C11 -179.39(19) . . . . ?
C10 C11 C12 N2 -2.7(4) . . . . ?
Cu1 O2 C13 O3 61.6(3) 2_656 . . . ?
Cu1 O2 C13 C14 -116.6(2) 2_656 . . . ?
Cu1 O3 C13 O2 22.4(4) . . . . ?
Cu1 O3 C13 C14 -159.39(17) . . . . ?
O2 C13 C14 C19 -172.7(2) . . . . ?
O3 C13 C14 C19 9.0(3) . . . . ?
O2 C13 C14 C15 10.3(3) . . . . ?
O3 C13 C14 C15 -168.1(2) . . . . ?
C19 C14 C15 C16 -2.6(4) . . . . ?
C13 C14 C15 C16 174.5(2) . . . . ?
C14 C15 C16 C17 3.1(4) . . . . ?
C14 C15 C16 C20 -175.9(2) . . . . ?
C15 C16 C17 C18 -1.4(4) . . . . ?
C20 C16 C17 C18 177.7(2) . . . . ?
C16 C17 C18 C19 -0.9(4) . . . . ?
C17 C18 C19 C14 1.5(4) . . . . ?
C15 C14 C19 C18 0.2(4) . . . . ?
C13 C14 C19 C18 -176.9(2) . . . . ?
C17 C16 C20 C21 127.8(3) . . . . ?
C15 C16 C20 C21 -53.2(3) . . . . ?
C17 C16 C20 C22 -54.3(3) . . . 2_766 ?
C15 C16 C20 C22 124.7(3) . . . 2_766 ?
C22 C20 C21 C22 -0.2(4) 2_766 . . . ?
C16 C20 C21 C22 177.7(2) . . . . ?
C20 C21 C22 C20 0.2(4) . . . 2_766 ?
C20 C21 C22 C23 179.1(2) . . . . ?
Cu1 O1 C23 O4 -6.1(3) 2_666 . . . ?
Cu1 O1 C23 C22 172.38(15) 2_666 . . . ?
C21 C22 C23 O4 92.5(3) . . . . ?
C20 C22 C23 O4 -88.6(3) 2_766 . . . ?
C21 C22 C23 O1 -86.0(3) . . . . ?
C20 C22 C23 O1 92.9(3) 2_766 . . . ?

_refine_diff_density_max         0.830
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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 1905205'
loop_
_audit_author_name
_audit_author_address
'Liming Fan'
;North University of China
China
;
_audit_update_record             
;
2019-03-24 deposited with the CCDC.	2019-07-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H13 Mn N2 O4'
_chemical_formula_sum            'C23 H13 Mn N2 O4'
_chemical_formula_weight         436.29

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   20.831(16)
_cell_length_b                   9.137(6)
_cell_length_c                   20.062(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.34(3)
_cell_angle_gamma                90
_cell_volume                     3795(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4221
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.97

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_F_000             1776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.730
_shelx_estimated_absorpt_T_min   0.844
_shelx_estimated_absorpt_T_max   0.868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6356
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18580
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.110
_diffrn_reflns_theta_max         27.612
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4385
_reflns_number_gt                2899
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+3.5885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         4385
_refine_ls_number_parameters     274
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.036
_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 0.31898(2) 0.68516(5) 0.41894(2) 0.02709(15) Uani 1 1 d . . . . .
O1 O 0.18200(11) 0.6008(2) 0.54127(10) 0.0380(5) Uani 1 1 d . . . . .
O2 O 0.22833(10) 0.6310(2) 0.44793(9) 0.0290(5) Uani 1 1 d . . . . .
O3 O 0.10572(10) 0.2782(3) 0.14782(9) 0.0387(6) Uani 1 1 d . . . . .
O4 O 0.20628(11) 0.2343(3) 0.18723(10) 0.0375(5) Uani 1 1 d . . . . .
N1 N 0.38129(13) 0.5811(3) 0.50660(13) 0.0355(6) Uani 1 1 d . . . . .
N2 N 0.34834(13) 0.4577(3) 0.38574(13) 0.0354(6) Uani 1 1 d . . . . .
C1 C 0.15034(16) 0.2772(3) 0.19486(14) 0.0306(7) Uani 1 1 d . . . . .
C2 C 0.13709(14) 0.3294(3) 0.26274(13) 0.0295(7) Uani 1 1 d . . . . .
C3 C 0.08407(15) 0.4164(4) 0.26966(15) 0.0389(8) Uani 1 1 d . . . . .
H3 H 0.054707 0.437536 0.232555 0.047 Uiso 1 1 calc R U . . .
C4 C 0.07478(16) 0.4720(4) 0.33200(16) 0.0412(8) Uani 1 1 d . . . . .
H4 H 0.039807 0.533037 0.336622 0.049 Uiso 1 1 calc R U . . .
C5 C 0.11699(15) 0.4374(3) 0.38684(15) 0.0316(7) Uani 1 1 d . U . . .
H5 H 0.1089(14) 0.474(4) 0.4294(16) 0.038 Uiso 1 1 d . U . . .
C6 C 0.16704(13) 0.3483(3) 0.37948(13) 0.0223(6) Uani 1 1 d . U . . .
C7 C 0.17836(14) 0.2938(3) 0.31892(13) 0.0278(6) Uani 1 1 d . . . . .
H7 H 0.213625 0.232962 0.315355 0.033 Uiso 1 1 calc R U . . .
C8 C 0.21165(13) 0.3000(3) 0.44204(12) 0.0236(6) Uani 1 1 d . . . . .
C9 C 0.22852(14) 0.3947(3) 0.49650(13) 0.0242(6) Uani 1 1 d . . . . .
C10 C 0.26545(14) 0.3421(3) 0.55273(13) 0.0256(6) Uani 1 1 d . . . . .
H10 H 0.275406 0.405084 0.588792 0.031 Uiso 1 1 calc R U . . .
C11 C 0.21174(14) 0.5547(3) 0.49474(13) 0.0250(6) Uani 1 1 d . . . . .
C12 C 0.39590(19) 0.6391(4) 0.56684(18) 0.0506(9) Uani 1 1 d . . . . .
H12 H 0.377579 0.728444 0.576372 0.061 Uiso 1 1 calc R U . . .
C13 C 0.4377(2) 0.5714(5) 0.6165(2) 0.0626(12) Uani 1 1 d . . . . .
H13 H 0.446352 0.614716 0.658507 0.075 Uiso 1 1 calc R U . . .
C14 C 0.46538(19) 0.4432(5) 0.6034(2) 0.0577(11) Uani 1 1 d . . . . .
H14 H 0.494185 0.398802 0.635993 0.069 Uiso 1 1 calc R U . . .
C15 C 0.45099(16) 0.3769(4) 0.54124(19) 0.0432(8) Uani 1 1 d . . . . .
C16 C 0.40747(15) 0.4499(3) 0.49425(16) 0.0339(7) Uani 1 1 d . . . . .
C17 C 0.38855(15) 0.3833(3) 0.43038(16) 0.0346(7) Uani 1 1 d . . . . .
C18 C 0.41172(17) 0.2430(4) 0.41718(19) 0.0464(9) Uani 1 1 d . . . . .
C19 C 0.4572(2) 0.1752(4) 0.4657(2) 0.0629(12) Uani 1 1 d . . . . .
H19 H 0.473531 0.083599 0.456402 0.075 Uiso 1 1 calc R U . . .
C20 C 0.47714(19) 0.2396(4) 0.5243(2) 0.0590(11) Uani 1 1 d . . . . .
H20 H 0.508302 0.194350 0.554102 0.071 Uiso 1 1 calc R U . . .
C21 C 0.3898(2) 0.1792(4) 0.3566(2) 0.0619(11) Uani 1 1 d . . . . .
H21 H 0.402606 0.084755 0.346988 0.074 Uiso 1 1 calc R U . . .
C22 C 0.3495(2) 0.2541(4) 0.3110(2) 0.0586(11) Uani 1 1 d . . . . .
H22 H 0.334997 0.212370 0.269778 0.070 Uiso 1 1 calc R U . . .
C23 C 0.33010(17) 0.3963(4) 0.32707(18) 0.0465(9) Uani 1 1 d . . . . .
H23 H 0.303522 0.448816 0.295302 0.056 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O2 2.096(2) . ?
Mn1 O1 2.113(2) 7_566 ?
Mn1 O4 2.184(3) 4 ?
Mn1 N1 2.275(3) . ?
Mn1 N2 2.286(3) . ?
Mn1 O3 2.332(2) 4 ?
Mn1 C1 2.579(3) 4 ?
O1 C11 1.249(3) . ?
O2 C11 1.248(3) . ?
O3 C1 1.249(3) . ?
O4 C1 1.255(4) . ?
N1 C12 1.324(4) . ?
N1 C16 1.352(4) . ?
N2 C23 1.321(4) . ?
N2 C17 1.342(4) . ?
C1 C2 1.497(4) . ?
C2 C7 1.379(4) . ?
C2 C3 1.380(4) . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.344(4) . ?
C5 H5 0.95(3) . ?
C6 C7 1.358(4) . ?
C6 C8 1.541(4) . ?
C7 H7 0.9300 . ?
C8 C10 1.383(4) 7_556 ?
C8 C9 1.407(4) . ?
C9 C10 1.380(4) . ?
C9 C11 1.503(4) . ?
C10 H10 0.9300 . ?
C12 C13 1.393(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.345(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.389(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.402(4) . ?
C15 C20 1.424(5) . ?
C16 C17 1.434(5) . ?
C17 C18 1.405(5) . ?
C18 C21 1.380(6) . ?
C18 C19 1.422(5) . ?
C19 C20 1.339(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.356(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.409(5) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Mn1 O1 93.86(8) . 7_566 ?
O2 Mn1 O4 101.05(9) . 4 ?
O1 Mn1 O4 99.61(9) 7_566 4 ?
O2 Mn1 N1 98.13(10) . . ?
O1 Mn1 N1 97.07(10) 7_566 . ?
O4 Mn1 N1 153.55(9) 4 . ?
O2 Mn1 N2 98.29(9) . . ?
O1 Mn1 N2 164.88(10) 7_566 . ?
O4 Mn1 N2 86.91(9) 4 . ?
N1 Mn1 N2 72.38(10) . . ?
O2 Mn1 O3 158.30(8) . 4 ?
O1 Mn1 O3 85.12(9) 7_566 4 ?
O4 Mn1 O3 57.99(9) 4 4 ?
N1 Mn1 O3 103.51(10) . 4 ?
N2 Mn1 O3 86.87(9) . 4 ?
O2 Mn1 C1 129.92(9) . 4 ?
O1 Mn1 C1 92.66(9) 7_566 4 ?
O4 Mn1 C1 29.07(9) 4 4 ?
N1 Mn1 C1 130.13(11) . 4 ?
N2 Mn1 C1 86.45(10) . 4 ?
O3 Mn1 C1 28.92(8) 4 4 ?
C11 O1 Mn1 128.35(19) . 7_566 ?
C11 O2 Mn1 132.33(19) . . ?
C1 O3 Mn1 86.54(19) . 4_545 ?
C1 O4 Mn1 93.21(17) . 4_545 ?
C12 N1 C16 117.7(3) . . ?
C12 N1 Mn1 126.3(2) . . ?
C16 N1 Mn1 115.9(2) . . ?
C23 N2 C17 118.5(3) . . ?
C23 N2 Mn1 125.8(2) . . ?
C17 N2 Mn1 115.7(2) . . ?
O3 C1 O4 122.3(3) . . ?
O3 C1 C2 119.2(3) . . ?
O4 C1 C2 118.5(3) . . ?
O3 C1 Mn1 64.53(16) . 4_545 ?
O4 C1 Mn1 57.72(15) . 4_545 ?
C2 C1 Mn1 176.2(2) . 4_545 ?
C7 C2 C3 119.2(3) . . ?
C7 C2 C1 120.5(3) . . ?
C3 C2 C1 120.3(3) . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 119.3(3) . . ?
C6 C5 H5 121.8(19) . . ?
C4 C5 H5 118.8(19) . . ?
C5 C6 C7 122.3(3) . . ?
C5 C6 C8 119.3(2) . . ?
C7 C6 C8 118.4(2) . . ?
C6 C7 C2 119.4(3) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
C10 C8 C9 117.6(2) 7_556 . ?
C10 C8 C6 120.2(2) 7_556 . ?
C9 C8 C6 122.2(2) . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 C11 117.7(2) . . ?
C8 C9 C11 122.8(2) . . ?
C9 C10 C8 123.1(2) . 7_556 ?
C9 C10 H10 118.5 . . ?
C8 C10 H10 118.5 7_556 . ?
O2 C11 O1 125.1(3) . . ?
O2 C11 C9 118.5(2) . . ?
O1 C11 C9 116.3(2) . . ?
N1 C12 C13 122.6(4) . . ?
N1 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
C14 C13 C12 119.6(4) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 117.1(3) . . ?
C14 C15 C20 123.2(4) . . ?
C16 C15 C20 119.6(4) . . ?
N1 C16 C15 122.9(3) . . ?
N1 C16 C17 117.6(3) . . ?
C15 C16 C17 119.5(3) . . ?
N2 C17 C18 122.6(3) . . ?
N2 C17 C16 118.1(3) . . ?
C18 C17 C16 119.3(3) . . ?
C21 C18 C17 117.6(4) . . ?
C21 C18 C19 123.3(4) . . ?
C17 C18 C19 119.0(4) . . ?
C20 C19 C18 121.8(4) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C15 120.5(4) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
C22 C21 C18 120.1(4) . . ?
C22 C21 H21 120.0 . . ?
C18 C21 H21 120.0 . . ?
C21 C22 C23 118.9(4) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
N2 C23 C22 122.3(4) . . ?
N2 C23 H23 118.9 . . ?
C22 C23 H23 118.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O3 C1 O4 0.0(3) 4_545 . . . ?
Mn1 O3 C1 C2 179.7(2) 4_545 . . . ?
Mn1 O4 C1 O3 0.0(3) 4_545 . . . ?
Mn1 O4 C1 C2 -179.7(2) 4_545 . . . ?
O3 C1 C2 C7 162.2(3) . . . . ?
O4 C1 C2 C7 -18.0(4) . . . . ?
O3 C1 C2 C3 -19.1(4) . . . . ?
O4 C1 C2 C3 160.6(3) . . . . ?
C7 C2 C3 C4 3.0(5) . . . . ?
C1 C2 C3 C4 -175.6(3) . . . . ?
C2 C3 C4 C5 -1.9(5) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C4 C5 C6 C7 1.7(5) . . . . ?
C4 C5 C6 C8 -175.4(3) . . . . ?
C5 C6 C7 C2 -0.5(4) . . . . ?
C8 C6 C7 C2 176.7(2) . . . . ?
C3 C2 C7 C6 -1.9(4) . . . . ?
C1 C2 C7 C6 176.8(3) . . . . ?
C5 C6 C8 C10 140.3(3) . . . 7_556 ?
C7 C6 C8 C10 -37.0(4) . . . 7_556 ?
C5 C6 C8 C9 -37.2(4) . . . . ?
C7 C6 C8 C9 145.5(3) . . . . ?
C10 C8 C9 C10 -1.4(5) 7_556 . . . ?
C6 C8 C9 C10 176.1(2) . . . . ?
C10 C8 C9 C11 174.5(3) 7_556 . . . ?
C6 C8 C9 C11 -8.0(4) . . . . ?
C8 C9 C10 C8 1.5(5) . . . 7_556 ?
C11 C9 C10 C8 -174.6(3) . . . 7_556 ?
Mn1 O2 C11 O1 117.2(3) . . . . ?
Mn1 O2 C11 C9 -62.5(3) . . . . ?
Mn1 O1 C11 O2 -26.4(4) 7_566 . . . ?
Mn1 O1 C11 C9 153.3(2) 7_566 . . . ?
C10 C9 C11 O2 122.0(3) . . . . ?
C8 C9 C11 O2 -54.0(4) . . . . ?
C10 C9 C11 O1 -57.8(4) . . . . ?
C8 C9 C11 O1 126.2(3) . . . . ?
C16 N1 C12 C13 1.3(5) . . . . ?
Mn1 N1 C12 C13 -176.0(3) . . . . ?
N1 C12 C13 C14 0.9(6) . . . . ?
C12 C13 C14 C15 -1.7(6) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C13 C14 C15 C20 -178.4(4) . . . . ?
C12 N1 C16 C15 -2.7(5) . . . . ?
Mn1 N1 C16 C15 174.9(2) . . . . ?
C12 N1 C16 C17 176.4(3) . . . . ?
Mn1 N1 C16 C17 -6.1(4) . . . . ?
C14 C15 C16 N1 1.9(5) . . . . ?
C20 C15 C16 N1 -179.3(3) . . . . ?
C14 C15 C16 C17 -177.1(3) . . . . ?
C20 C15 C16 C17 1.7(5) . . . . ?
C23 N2 C17 C18 -0.2(5) . . . . ?
Mn1 N2 C17 C18 -179.1(2) . . . . ?
C23 N2 C17 C16 -179.2(3) . . . . ?
Mn1 N2 C17 C16 1.8(4) . . . . ?
N1 C16 C17 N2 2.8(4) . . . . ?
C15 C16 C17 N2 -178.1(3) . . . . ?
N1 C16 C17 C18 -176.2(3) . . . . ?
C15 C16 C17 C18 2.9(5) . . . . ?
N2 C17 C18 C21 -2.4(5) . . . . ?
C16 C17 C18 C21 176.6(3) . . . . ?
N2 C17 C18 C19 176.3(3) . . . . ?
C16 C17 C18 C19 -4.7(5) . . . . ?
C21 C18 C19 C20 -179.5(4) . . . . ?
C17 C18 C19 C20 1.9(6) . . . . ?
C18 C19 C20 C15 2.7(6) . . . . ?
C14 C15 C20 C19 174.2(4) . . . . ?
C16 C15 C20 C19 -4.5(5) . . . . ?
C17 C18 C21 C22 2.8(6) . . . . ?
C19 C18 C21 C22 -175.8(4) . . . . ?
C18 C21 C22 C23 -0.9(6) . . . . ?
C17 N2 C23 C22 2.4(5) . . . . ?
Mn1 N2 C23 C22 -178.8(3) . . . . ?
C21 C22 C23 N2 -1.9(6) . . . . ?

_refine_diff_density_max         0.511
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1938459'
loop_
_audit_author_name
_audit_author_address
'Liming Fan'
;North University of China
China
;
_audit_update_record             
;
2019-07-04 deposited with the CCDC.	2019-07-30 downloaded from the CCDC.
;
_audit_creation_date             2018-04-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.14 svn.r3398 for OlexSys, GUI svn.r5328)
;
_chemical_formula_moiety         'C46 H26 Cd2 N4 O8'
_chemical_formula_sum            'C46 H26 Cd2 N4 O8'
_chemical_formula_weight         987.56
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cd -0.80524 1.22862 19.22140 17.64440 4.46100 1.60290 0.59460 6.90890 24.70080
87.48250 5.06939983368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   9.7425(4)
_cell_length_b                   9.7964(4)
_cell_length_c                   10.3959(5)
_cell_angle_alpha                77.963(1)
_cell_angle_beta                 81.976(1)
_cell_angle_gamma                69.656(1)
_cell_volume                     907.42(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.507
_cell_measurement_theta_min      3.114
_exptl_absorpt_coefficient_mu    1.239
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1131 before and 0.0411 after correction.
The Ratio of minimum to maximum transmission is 0.7753.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_description       block
_exptl_crystal_density_diffrn    1.8071
_exptl_crystal_F_000             488.6085
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.079
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19033
_diffrn_reflns_theta_full        27.5139
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.11
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9971
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71076
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                3902
_reflns_number_total             4172
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.7697
_refine_diff_density_min         -0.4876
_refine_diff_density_rms         0.0796
_refine_ls_d_res_high            0.7693
_refine_ls_d_res_low             6.5431
_refine_ls_goodness_of_fit_ref   1.0489
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0236
_refine_ls_restrained_S_all      1.0489
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0321P)²+0.7068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0620
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 c7(H7), c6(H6), c16(H16), c17(H17), c18(H18), c15(H15), c12(H12), c10(H10),
 c11(H11), c1(H1), c2(H2), c3(H3), c21(H21)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Cd1 Cd 0.345722(16) 0.532089(15) 0.641137(14) 0.02613(6) Uani 1.000000 .
o3 O 0.73265(18) -0.35527(18) 0.18750(19) 0.0417(4) Uani 1.000000 .
o2 O 0.4449(2) 0.3988(2) 0.43075(19) 0.0477(5) Uani 1.000000 .
o1 O 0.2139(2) 0.4858(2) 0.50019(19) 0.0513(5) Uani 1.000000 .
o4 O 0.5006(2) -0.3284(2) 0.2341(2) 0.0503(5) Uani 1.000000 .
n2 N 0.2370(2) 0.7785(2) 0.53804(19) 0.0329(4) Uani 1.000000 .
n1 N 0.2699(2) 0.6892(2) 0.80189(19) 0.0344(4) Uani 1.000000 .
c19 C 0.3075(2) 0.2489(2) 0.12701(17) 0.0208(4) Uani 1.000000 .
c23 C 0.6021(2) -0.2850(2) 0.1718(2) 0.0268(4) Uani 1.000000 .
c22 C 0.5561(2) -0.1390(2) 0.0786(2) 0.0243(4) Uani 1.000000 .
c13 C 0.3123(3) 0.4269(2) 0.4182(2) 0.0310(5) Uani 1.000000 .
c20 C 0.4096(2) 0.1232(2) 0.0582(2) 0.0237(4) Uani 1.000000 .
c21 C 0.4679(2) -0.0161(2) 0.1332(2) 0.0262(4) Uani 1.000000 .
c15 C 0.3592(2) 0.2850(2) 0.2301(2) 0.0260(4) Uani 1.000000 .
c14 C 0.2630(2) 0.3884(2) 0.3034(2) 0.0256(4) Uani 1.000000 .
c18 C 0.1662(3) 0.3126(2) 0.0986(2) 0.0301(4) Uani 1.000000 .
c17 C 0.0688(2) 0.4172(2) 0.1700(2) 0.0321(5) Uani 1.000000 .
c12 C 0.2188(3) 0.8207(3) 0.4108(3) 0.0410(6) Uani 1.000000 .
c16 C 0.1167(2) 0.4537(2) 0.2730(2) 0.0304(5) Uani 1.000000 .
c5 C 0.2240(2) 0.8357(3) 0.7537(2) 0.0326(5) Uani 1.000000 .
c9 C 0.2098(2) 0.8826(2) 0.6139(2) 0.0317(5) Uani 1.000000 .
c8 C 0.1651(3) 1.0349(3) 0.5596(3) 0.0433(6) Uani 1.000000 .
c1 C 0.2826(3) 0.6460(3) 0.9305(3) 0.0474(6) Uani 1.000000 .
c11 C 0.1723(3) 0.9687(3) 0.3504(3) 0.0480(7) Uani 1.000000 .
c4 C 0.1914(3) 0.9437(3) 0.8337(3) 0.0461(6) Uani 1.000000 .
c10 C 0.1468(3) 1.0743(3) 0.4242(3) 0.0496(7) Uani 1.000000 .
c7 C 0.1377(4) 1.1399(3) 0.6440(4) 0.0588(8) Uani 1.000000 .
c6 C 0.1479(4) 1.0973(3) 0.7739(4) 0.0631(9) Uani 1.000000 .
c3 C 0.2064(4) 0.8935(4) 0.9684(3) 0.0631(9) Uani 1.000000 .
c2 C 0.2523(4) 0.7449(4) 1.0177(3) 0.0621(9) Uani 1.000000 .
H7 H 0.1123(4) 1.2399(3) 0.6081(4) 0.0706(10) Uiso 1.000000 R
H6 H 0.1263(4) 1.1686(3) 0.8271(4) 0.0757(11) Uiso 1.000000 R
H16 H 0.0516(2) 0.5218(2) 0.3220(2) 0.0364(5) Uiso 1.000000 R
H17 H -0.0281(2) 0.4622(2) 0.1483(2) 0.0385(6) Uiso 1.000000 R
H18 H 0.1332(3) 0.2865(2) 0.0306(2) 0.0361(5) Uiso 1.000000 R
H15 H 0.4569(2) 0.2403(2) 0.2497(2) 0.0313(5) Uiso 1.000000 R
H12 H 0.2378(3) 0.7485(3) 0.3590(3) 0.0492(7) Uiso 1.000000 R
H10 H 0.1171(3) 1.1734(3) 0.3851(3) 0.0596(8) Uiso 1.000000 R
H11 H 0.1591(3) 0.9942(3) 0.2606(3) 0.0576(8) Uiso 1.000000 R
H1 H 0.3130(3) 0.5453(3) 0.9640(3) 0.0568(8) Uiso 1.000000 R
H2 H 0.2630(4) 0.7110(4) 1.1074(3) 0.0745(10) Uiso 1.000000 R
H3 H 0.1852(4) 0.9612(4) 1.0251(3) 0.0757(11) Uiso 1.000000 R
H21 H 0.4471(2) -0.0277(2) 0.2241(2) 0.0314(5) Uiso 1.000000 R


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 o3 2.4515(17) 2_656 ?
Cd1 o2 2.3457(18) 2_666 ?
Cd1 o1 2.2820(19) . ?
Cd1 o4 2.3006(17) 2_656 ?
Cd1 n2 2.3572(19) . ?
Cd1 n1 2.376(2) . ?
o3 c23 1.233(3) . ?
o2 c13 1.243(3) . ?
o1 c13 1.254(3) . ?
o4 c23 1.256(3) . ?
n2 c12 1.319(3) . ?
n2 c9 1.350(3) . ?
n1 c5 1.352(3) . ?
n1 c1 1.325(3) . ?
c19 c20 1.528(2) . ?
c19 c15 1.400(3) . ?
c19 c18 1.346(3) . ?
c23 c22 1.511(3) . ?
c22 c20 1.403(3) 2_655 ?
c22 c21 1.393(3) . ?
c13 c14 1.507(3) . ?
c20 c21 1.391(3) . ?
c21 H21 0.9300 . ?
c15 c14 1.395(3) . ?
c15 H15 0.9300 . ?
c14 c16 1.396(3) . ?
c18 c17 1.395(3) . ?
c18 H18 0.9300 . ?
c17 c16 1.381(3) . ?
c17 H17 0.9300 . ?
c12 c11 1.394(4) . ?
c12 H12 0.9300 . ?
c16 H16 0.9300 . ?
c5 c9 1.441(3) . ?
c5 c4 1.405(3) . ?
c9 c8 1.414(3) . ?
c8 c10 1.399(4) . ?
c8 c7 1.421(4) . ?
c1 c2 1.393(4) . ?
c1 H1 0.9300 . ?
c11 c10 1.349(4) . ?
c11 H11 0.9300 . ?
c4 c6 1.438(4) . ?
c4 c3 1.394(5) . ?
c10 H10 0.9300 . ?
c7 c6 1.335(5) . ?
c7 H7 0.9300 . ?
c6 H6 0.9300 . ?
c3 c2 1.372(5) . ?
c3 H3 0.9300 . ?
c2 H2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
o2 Cd1 o3 139.33(6) 2_666 2_656 ?
o1 Cd1 o3 87.48(7) . 2_656 ?
o1 Cd1 o2 122.48(7) . 2_666 ?
o4 Cd1 o3 54.48(6) 2_656 2_656 ?
o4 Cd1 o2 85.97(7) 2_656 2_666 ?
o4 Cd1 o1 116.18(8) 2_656 . ?
n2 Cd1 o3 135.90(6) . 2_656 ?
n2 Cd1 o2 79.42(7) . 2_666 ?
n2 Cd1 o1 82.54(7) . . ?
n2 Cd1 o4 160.71(8) . 2_656 ?
n1 Cd1 o3 84.90(7) . 2_656 ?
n1 Cd1 o2 92.54(7) . 2_666 ?
n1 Cd1 o1 130.83(7) . . ?
n1 Cd1 o4 97.98(8) . 2_656 ?
n1 Cd1 n2 70.39(7) . . ?
c23 o3 Cd1 88.36(14) . 2_656 ?
c13 o2 Cd1 146.18(17) . 2_666 ?
c13 o1 Cd1 102.11(16) . . ?
c23 o4 Cd1 94.83(13) . 2_656 ?
c12 n2 Cd1 124.65(17) . . ?
c9 n2 Cd1 115.95(15) . . ?
c9 n2 c12 118.8(2) . . ?
c5 n1 Cd1 115.47(15) . . ?
c1 n1 Cd1 125.76(18) . . ?
c1 n1 c5 118.4(2) . . ?
c15 c19 c20 118.61(18) . . ?
c18 c19 c20 120.41(18) . . ?
c18 c19 c15 120.59(18) . . ?
o4 c23 o3 122.2(2) . . ?
c22 c23 o3 121.3(2) . . ?
c22 c23 o4 116.43(19) . . ?
c20 c22 c23 123.83(17) 2_655 . ?
c21 c22 c23 116.82(18) . . ?
c21 c22 c20 119.27(18) . 2_655 ?
o1 c13 o2 122.2(2) . . ?
c14 c13 o2 120.9(2) . . ?
c14 c13 o1 116.9(2) . . ?
c22 c20 c19 123.40(17) 2_655 . ?
c21 c20 c19 118.92(17) . . ?
c21 c20 c22 117.63(17) . 2_655 ?
c20 c21 c22 123.10(19) . . ?
H21 c21 c22 118.45(12) . . ?
H21 c21 c20 118.45(12) . . ?
c14 c15 c19 119.44(19) . . ?
H15 c15 c19 120.28(11) . . ?
H15 c15 c14 120.28(12) . . ?
c15 c14 c13 121.36(19) . . ?
c16 c14 c13 119.14(19) . . ?
c16 c14 c15 119.46(19) . . ?
c17 c18 c19 120.8(2) . . ?
H18 c18 c19 119.62(12) . . ?
H18 c18 c17 119.62(13) . . ?
c16 c17 c18 119.8(2) . . ?
H17 c17 c18 120.12(13) . . ?
H17 c17 c16 120.12(12) . . ?
c11 c12 n2 123.0(3) . . ?
H12 c12 n2 118.50(15) . . ?
H12 c12 c11 118.50(17) . . ?
c17 c16 c14 119.96(19) . . ?
H16 c16 c14 120.02(12) . . ?
H16 c16 c17 120.02(12) . . ?
c9 c5 n1 118.4(2) . . ?
c4 c5 n1 122.9(2) . . ?
c4 c5 c9 118.7(2) . . ?
c5 c9 n2 118.4(2) . . ?
c8 c9 n2 121.6(2) . . ?
c8 c9 c5 120.0(2) . . ?
c10 c8 c9 117.5(2) . . ?
c7 c8 c9 119.2(3) . . ?
c7 c8 c10 123.3(3) . . ?
c2 c1 n1 122.9(3) . . ?
H1 c1 n1 118.56(16) . . ?
H1 c1 c2 118.56(19) . . ?
c10 c11 c12 119.0(3) . . ?
H11 c11 c12 120.50(17) . . ?
H11 c11 c10 120.50(16) . . ?
c6 c4 c5 119.3(3) . . ?
c3 c4 c5 116.8(3) . . ?
c3 c4 c6 123.8(3) . . ?
c11 c10 c8 120.1(2) . . ?
H10 c10 c8 119.96(16) . . ?
H10 c10 c11 119.96(16) . . ?
c6 c7 c8 121.1(3) . . ?
H7 c7 c8 119.47(18) . . ?
H7 c7 c6 119.47(17) . . ?
c7 c6 c4 121.6(3) . . ?
H6 c6 c4 119.18(18) . . ?
H6 c6 c7 119.18(17) . . ?
c2 c3 c4 120.4(3) . . ?
H3 c3 c4 119.78(18) . . ?
H3 c3 c2 119.78(18) . . ?
c3 c2 c1 118.6(3) . . ?
H2 c2 c1 120.72(19) . . ?
H2 c2 c3 120.72(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
