# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_19101309-1
_audit_block_doi                 10.5517/ccdc.csd.cc24j786
_database_code_depnum_ccdc_archive 'CCDC 1981807'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0RA05690A 2020
loop_
_audit_author_name
_audit_author_address
'Chuxin LIANG'
;Guilin University of Technology
China
;
_audit_update_record             
;
2020-02-04 deposited with the CCDC.	2021-01-15 downloaded from the CCDC.
;
_audit_creation_date             2020-02-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H12 Mn N2 O5'
_chemical_formula_sum            'C20 H12 Mn N2 O5'
_chemical_formula_weight         415.26
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   4.8722(2)
_cell_length_b                   16.6989(6)
_cell_length_c                   19.3540(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1574.65(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2826
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7510
_cell_measurement_theta_min      3.7960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.879
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.752
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       bolck
_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11654
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.162
_diffrn_reflns_theta_min         3.385
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.648
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.827
_reflns_number_gt                3026
_reflns_number_total             3741
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Flack x determined using 1047 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.018(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3741
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0308P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0883
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Rotating group:
 O5(H5A)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C14(H14), C8(H8), C2(H2), C3(H3), C11(H11), C17(H17), C16(H16),
 C4(H4), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.04438(13) 0.69435(4) 0.05364(3) 0.01853(16) Uani 1 1 d . . . . .
O1 O -0.1266(5) 0.80760(17) 0.02376(13) 0.0188(6) Uani 1 1 d . . . . .
C6 C -0.0099(8) 1.0220(2) 0.05518(19) 0.0186(9) Uani 1 1 d . . . . .
C5 C 0.1916(9) 1.0468(3) 0.0073(2) 0.0239(10) Uani 1 1 d . . . . .
H5 H 0.2738 1.0090 -0.0213 0.029 Uiso 1 1 calc R . . . .
N5 N -0.3308(7) 1.0640(2) 0.14681(17) 0.0227(8) Uani 1 1 d . . . . .
N6 N -0.7449(8) 0.9007(2) 0.20659(16) 0.0215(8) Uani 1 1 d . . . . .
C13 C -1.0294(9) 0.9437(2) 0.30539(19) 0.0203(9) Uani 1 1 d . . . . .
C18 C -0.9444(9) 0.8862(2) 0.25455(18) 0.0188(9) Uani 1 1 d . . . . .
C14 C -1.2405(10) 0.9211(3) 0.3515(2) 0.0270(10) Uani 1 1 d . . . . .
H14 H -1.2984 0.9572 0.3851 0.032 Uiso 1 1 calc R . . . .
C8 C -0.3046(9) 0.9270(2) 0.11199(19) 0.0186(9) Uani 1 1 d . . . . .
H8 H -0.3702 0.8751 0.1174 0.022 Uiso 1 1 calc R . . . .
C20 C 0.0238(9) 0.8710(2) 0.02919(17) 0.0177(9) Uani 1 1 d . . . . .
C2 C -0.0525(10) 1.1619(2) 0.0917(2) 0.0308(11) Uani 1 1 d . . . . .
H2 H -0.1337 1.2008 0.1193 0.037 Uiso 1 1 calc R . . . .
C9 C -0.4141(9) 0.9891(2) 0.15300(19) 0.0195(9) Uani 1 1 d . . . . .
C7 C -0.1039(8) 0.9420(2) 0.06455(19) 0.0174(9) Uani 1 1 d . . . . .
C1 C -0.1342(9) 1.0811(3) 0.0985(2) 0.0232(10) Uani 1 1 d . . . . .
C3 C 0.1442(9) 1.1835(3) 0.0450(2) 0.0313(11) Uani 1 1 d . . . . .
H3 H 0.1969 1.2368 0.0412 0.038 Uiso 1 1 calc R . . . .
C11 C -0.6977(9) 1.0333(3) 0.2543(2) 0.0233(10) Uani 1 1 d . . . . .
H11 H -0.6104 1.0828 0.2524 0.028 Uiso 1 1 calc R . . . .
C17 C -1.0725(9) 0.8100(3) 0.2532(2) 0.0280(10) Uani 1 1 d . . . . .
H17 H -1.0151 0.7720 0.2212 0.034 Uiso 1 1 calc R . . . .
C10 C -0.6257(9) 0.9725(3) 0.2059(2) 0.0201(9) Uani 1 1 d . . . . .
C16 C -1.2789(10) 0.7916(3) 0.2982(2) 0.0305(11) Uani 1 1 d . . . . .
H16 H -1.3648 0.7420 0.2958 0.037 Uiso 1 1 calc R . . . .
C12 C -0.8932(9) 1.0199(2) 0.30357(19) 0.0207(10) Uani 1 1 d . . . . .
C4 C 0.2678(10) 1.1252(3) 0.0024(2) 0.0285(11) Uani 1 1 d . . . . .
H4 H 0.4019 1.1403 -0.0293 0.034 Uiso 1 1 calc R . . . .
C15 C -1.3612(9) 0.8475(3) 0.3478(2) 0.0289(11) Uani 1 1 d . . . . .
H15 H -1.5000 0.8343 0.3788 0.035 Uiso 1 1 calc R . . . .
O2 O 0.2651(6) 0.87390(17) 0.00940(14) 0.0254(7) Uani 1 1 d . . . . .
C19 C -0.9527(9) 1.0865(2) 0.35409(19) 0.0209(9) Uani 1 1 d . . . . .
O4 O -1.1453(6) 1.08036(18) 0.39683(14) 0.0282(7) Uani 1 1 d . . . . .
O3 O -0.8011(6) 1.14883(18) 0.35286(15) 0.0276(7) Uani 1 1 d . . . . .
O5 O 0.3385(7) 0.7485(2) 0.12709(16) 0.0303(8) Uani 1 1 d . . . . .
H5A H 0.4592 0.7133 0.1393 0.046 Uiso 1 1 d GR . . . .
H5B H 0.342(13) 0.791(4) 0.151(3) 0.10(3) Uiso 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 2.146(3) . ?
Mn1 O1 2.194(3) 3_565 ?
Mn1 O2 2.154(3) 3_465 ?
Mn1 C19 2.575(4) 4_445 ?
Mn1 O4 2.187(3) 4_445 ?
Mn1 O3 2.293(3) 4_445 ?
Mn1 O5 2.212(3) . ?
O1 Mn1 2.194(3) 3_465 ?
O1 C20 1.292(5) . ?
C6 C5 1.412(6) . ?
C6 C7 1.424(5) . ?
C6 C1 1.429(5) . ?
C5 C4 1.364(6) . ?
N5 C9 1.322(5) . ?
N5 C1 1.368(5) . ?
N6 C18 1.366(5) . ?
N6 C10 1.332(5) . ?
C13 C18 1.435(5) . ?
C13 C14 1.413(6) . ?
C13 C12 1.436(6) . ?
C18 C17 1.418(6) . ?
C14 C15 1.364(6) . ?
C8 C9 1.410(5) . ?
C8 C7 1.365(5) . ?
C20 C7 1.504(5) . ?
C20 O2 1.237(5) . ?
C2 C1 1.413(6) . ?
C2 C3 1.366(6) . ?
C9 C10 1.479(5) . ?
C3 C4 1.411(6) . ?
C11 C10 1.425(5) . ?
C11 C12 1.366(6) . ?
C17 C16 1.364(6) . ?
C16 C15 1.398(6) . ?
C12 C19 1.509(5) . ?
O2 Mn1 2.154(3) 3_565 ?
C19 Mn1 2.575(4) 4_455 ?
C19 O4 1.255(5) . ?
C19 O3 1.277(5) . ?
O4 Mn1 2.187(3) 4_455 ?
O3 Mn1 2.293(3) 4_455 ?

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 O1 96.47(7) . 3_565 ?
O1 Mn1 O2 93.92(11) . 3_465 ?
O1 Mn1 C19 137.38(12) . 4_445 ?
O1 Mn1 C19 126.13(13) 3_565 4_445 ?
O1 Mn1 O4 166.49(10) . 4_445 ?
O1 Mn1 O3 155.72(11) 3_565 4_445 ?
O1 Mn1 O3 107.71(10) . 4_445 ?
O1 Mn1 O5 88.37(12) 3_565 . ?
O1 Mn1 O5 93.68(12) . . ?
O2 Mn1 O1 93.84(10) 3_465 3_565 ?
O2 Mn1 C19 85.02(12) 3_465 4_445 ?
O2 Mn1 O4 85.97(11) 3_465 4_445 ?
O2 Mn1 O3 86.85(11) 3_465 4_445 ?
O2 Mn1 O5 171.80(12) 3_465 . ?
O4 Mn1 O1 97.01(11) 4_445 3_565 ?
O4 Mn1 C19 29.12(12) 4_445 4_445 ?
O4 Mn1 O3 58.79(11) 4_445 4_445 ?
O4 Mn1 O5 85.92(12) 4_445 . ?
O3 Mn1 C19 29.69(12) 4_445 4_445 ?
O5 Mn1 C19 87.30(13) . 4_445 ?
O5 Mn1 O3 87.90(12) . 4_445 ?
Mn1 O1 Mn1 117.03(12) . 3_465 ?
C20 O1 Mn1 118.8(2) . 3_465 ?
C20 O1 Mn1 118.7(2) . . ?
C5 C6 C7 125.6(4) . . ?
C5 C6 C1 118.5(4) . . ?
C7 C6 C1 115.9(4) . . ?
C4 C5 C6 121.1(4) . . ?
C9 N5 C1 118.3(3) . . ?
C10 N6 C18 118.4(4) . . ?
C18 C13 C12 116.2(4) . . ?
C14 C13 C18 117.7(4) . . ?
C14 C13 C12 126.0(4) . . ?
N6 C18 C13 123.6(4) . . ?
N6 C18 C17 117.4(4) . . ?
C17 C18 C13 119.0(4) . . ?
C15 C14 C13 121.4(4) . . ?
C7 C8 C9 121.0(4) . . ?
O1 C20 C7 116.6(4) . . ?
O2 C20 O1 123.1(4) . . ?
O2 C20 C7 120.2(4) . . ?
C3 C2 C1 120.8(4) . . ?
N5 C9 C8 121.9(4) . . ?
N5 C9 C10 117.0(4) . . ?
C8 C9 C10 121.1(4) . . ?
C6 C7 C20 123.3(4) . . ?
C8 C7 C6 119.2(4) . . ?
C8 C7 C20 117.3(4) . . ?
N5 C1 C6 123.7(4) . . ?
N5 C1 C2 117.4(4) . . ?
C2 C1 C6 119.0(4) . . ?
C2 C3 C4 120.3(4) . . ?
C12 C11 C10 120.9(4) . . ?
C16 C17 C18 121.0(4) . . ?
N6 C10 C9 118.6(4) . . ?
N6 C10 C11 121.8(4) . . ?
C11 C10 C9 119.6(4) . . ?
C17 C16 C15 120.0(4) . . ?
C13 C12 C19 123.3(4) . . ?
C11 C12 C13 119.0(4) . . ?
C11 C12 C19 117.7(4) . . ?
C5 C4 C3 120.3(4) . . ?
C14 C15 C16 120.9(4) . . ?
C20 O2 Mn1 139.0(3) . 3_565 ?
C12 C19 Mn1 176.4(3) . 4_455 ?
O4 C19 Mn1 58.0(2) . 4_455 ?
O4 C19 C12 120.7(4) . . ?
O4 C19 O3 120.7(4) . . ?
O3 C19 Mn1 62.8(2) . 4_455 ?
O3 C19 C12 118.5(4) . . ?
C19 O4 Mn1 92.9(2) . 4_455 ?
C19 O3 Mn1 87.5(2) . 4_455 ?

_olex2_submission_special_instructions 'No special instructions were received'
