# Electronic Supplementary Material (ESI) for ChemComm.
# 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_20190310-35_sq
_database_code_depnum_ccdc_archive 'CCDC 2086200'
loop_
_audit_author_name
_audit_author_address
'Jian-Hua Qin'
;luoyang normal university
China
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;
_audit_creation_date             2020-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C48 H32 Mn2 N4 O12'
_chemical_formula_sum            'C48 H32 Mn2 N4 O12'
_chemical_formula_weight         966.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1O1N1Mn1
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      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
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                   14.0571(5)
_cell_length_b                   17.3975(6)
_cell_length_c                   13.7185(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.085(4)
_cell_angle_gamma                90
_cell_volume                     3223.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11565
_cell_measurement_temperature    293.24(10)
_cell_measurement_theta_max      27.7550
_cell_measurement_theta_min      3.7380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    0.996
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31852
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.450
_diffrn_reflns_theta_min         3.673
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.24(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00  13.00   1.00   17.50    --  -13.80 -77.00 -90.00   94
  2  ω    -62.00   6.00   1.00   17.50    --  -13.80 115.00-103.00   68
  3  ω    -20.00  25.00   1.00   17.50    --  -13.80 -99.00 150.00   45
  4  ω    -52.00  32.00   1.00   17.50    --   14.82 -57.00  30.00   84
  5  ω    -52.00  32.00   1.00   17.50    --   14.82 -57.00  60.00   84
  6  ω     -4.00  84.00   1.00   17.50    --   14.82  38.00-150.00   88
  7  ω    -20.00  25.00   1.00   17.50    --  -13.80 -99.00 -60.00   45
  8  ω    -81.00   3.00   1.00   17.50    --  -13.80 -57.00  30.00   84
  9  ω    -20.00  54.00   1.00   17.50    --   14.82 -99.00 150.00   74
 10  ω    -52.00  32.00   1.00   17.50    --   14.82 -57.00 -90.00   84
 11  ω    -52.00  32.00   1.00   17.50    --   14.82 -57.00-180.00   84
 12  ω    -20.00  54.00   1.00   17.50    --   14.82 -99.00-120.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0202751000
_diffrn_orient_matrix_UB_12      -0.0338231000
_diffrn_orient_matrix_UB_13      0.0151068000
_diffrn_orient_matrix_UB_21      0.0174068000
_diffrn_orient_matrix_UB_22      -0.0217325000
_diffrn_orient_matrix_UB_23      -0.0352779000
_diffrn_orient_matrix_UB_31      0.0452116000
_diffrn_orient_matrix_UB_32      -0.0067945000
_diffrn_orient_matrix_UB_33      0.0377278000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2991
_reflns_number_total             3851
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3851
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.106
_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)+(0.0719P)²+0.4422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1282
_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. Restrained distances
 O3-H3 = O4-H4
 0.87 with sigma of 0.02
3.a Fixed occupancy and ADP/Uiso:
 H3, H4
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 1.000000 1.000000 0.500000 0.02729(16) Uani 1 4 d S T P . .
Mn2 Mn 0.500000 0.500000 0.000000 0.03070(17) Uani 1 4 d S T P . .
O1 O 0.58318(11) 0.59006(9) 0.09823(11) 0.0523(4) Uani 1 1 d . . . . .
O2 O 0.49367(11) 0.60923(9) 0.20702(13) 0.0570(4) Uani 1 1 d . . . . .
O3 O 1.05692(17) 1.000000 0.36264(16) 0.0498(5) Uani 1 2 d DS T P . .
H3 H 1.0440(19) 1.0410(11) 0.3285(18) 0.075 Uiso 1 1 d D . . . .
O4 O 0.38566(15) 0.500000 0.08568(16) 0.0440(5) Uani 1 2 d DS T P . .
H4 H 0.4032(18) 0.5373(11) 0.1259(17) 0.066 Uiso 1 1 d D . . . .
N1 N 1.000000 0.88453(11) 0.500000 0.0304(4) Uani 1 2 d S T P . .
N2 N 0.86312(15) 1.000000 0.40313(16) 0.0353(5) Uani 1 2 d S T P . .
C1 C 0.71879(16) 0.96143(13) 0.28891(18) 0.0596(6) Uani 1 1 d . . . . .
H1 H 0.669300 0.929794 0.250126 0.071 Uiso 1 1 calc R . . . .
C2 C 0.80902(14) 0.93677(11) 0.35962(15) 0.0416(5) Uani 1 1 d . . . . .
C3 C 0.83699(13) 0.86030(10) 0.37818(13) 0.0366(4) Uani 1 1 d . . . . .
C4 C 0.92653(12) 0.83685(10) 0.44446(13) 0.0331(4) Uani 1 1 d . . . . .
C5 C 0.95542(14) 0.75851(10) 0.46623(14) 0.0397(4) Uani 1 1 d . . . . .
H5 H 0.918799 0.715375 0.438414 0.048 Uiso 1 1 calc R . . . .
C6 C 0.76739(14) 0.79929(11) 0.32400(15) 0.0396(4) Uani 1 1 d . . . . .
C7 C 0.7808(2) 0.76334(16) 0.2399(2) 0.0715(8) Uani 1 1 d . . . . .
H7 H 0.833840 0.777165 0.215415 0.086 Uiso 1 1 calc R . . . .
C8 C 0.7158(2) 0.70651(16) 0.1911(2) 0.0720(8) Uani 1 1 d . . . . .
H8 H 0.726027 0.682571 0.134188 0.086 Uiso 1 1 calc R . . . .
C9 C 0.63714(14) 0.68503(11) 0.22490(14) 0.0402(4) Uani 1 1 d . . . . .
C10 C 0.62352(18) 0.72113(14) 0.30795(18) 0.0596(6) Uani 1 1 d . . . . .
H10 H 0.570332 0.707289 0.332167 0.072 Uiso 1 1 calc R . . . .
C11 C 0.68765(18) 0.77809(14) 0.35683(18) 0.0615(7) Uani 1 1 d . . . . .
H11 H 0.676466 0.802453 0.412983 0.074 Uiso 1 1 calc R . . . .
C12 C 0.56527(15) 0.62324(11) 0.17214(14) 0.0417(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
Mn1 O3 2.242(2) . ?
Mn1 O3 2.242(2) 5_776 ?
Mn1 N1 2.0089(19) 5_776 ?
Mn1 N1 2.0089(19) . ?
Mn1 N2 2.0128(19) 5_776 ?
Mn1 N2 2.0128(19) . ?
Mn2 O1 2.1828(12) 2_655 ?
Mn2 O1 2.1828(12) . ?
Mn2 O1 2.1828(12) 6_565 ?
Mn2 O1 2.1828(12) 5_665 ?
Mn2 O4 2.239(2) . ?
Mn2 O4 2.239(2) 5_665 ?
O1 C12 1.251(2) . ?
O2 C12 1.252(2) . ?
O3 H3 0.844(16) . ?
O3 H3 0.844(16) 6_575 ?
O4 H4 0.843(15) . ?
O4 H4 0.843(15) 6_565 ?
N1 C4 1.378(2) . ?
N1 C4 1.378(2) 2_756 ?
N2 C2 1.376(2) . ?
N2 C2 1.376(2) 6_575 ?
C1 C1 1.342(5) 6_575 ?
C1 H1 0.9300 . ?
C1 C2 1.433(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.394(2) . ?
C3 C6 1.494(2) . ?
C4 C5 1.430(3) . ?
C5 C5 1.336(4) 2_756 ?
C5 H5 0.9300 . ?
C6 C7 1.371(3) . ?
C6 C11 1.369(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.365(3) . ?
C9 C10 1.360(3) . ?
C9 C12 1.515(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Mn1 O3 180.00(12) . 5_776 ?
N1 Mn1 O3 90.000(1) 5_776 5_776 ?
N1 Mn1 O3 90.000(1) . . ?
N1 Mn1 O3 90.000(1) . 5_776 ?
N1 Mn1 O3 90.000(1) 5_776 . ?
N1 Mn1 N1 180.0 . 5_776 ?
N1 Mn1 N2 90.000(1) 5_776 . ?
N1 Mn1 N2 90.000(1) . . ?
N1 Mn1 N2 90.000(1) . 5_776 ?
N1 Mn1 N2 90.000(1) 5_776 5_776 ?
N2 Mn1 O3 86.77(9) 5_776 5_776 ?
N2 Mn1 O3 93.24(9) 5_776 . ?
N2 Mn1 O3 93.23(9) . 5_776 ?
N2 Mn1 O3 86.76(9) . . ?
N2 Mn1 N2 180.00(13) 5_776 . ?
O1 Mn2 O1 91.74(9) 6_565 . ?
O1 Mn2 O1 88.26(8) 5_665 6_565 ?
O1 Mn2 O1 180.0 5_665 . ?
O1 Mn2 O1 91.74(9) 5_665 2_655 ?
O1 Mn2 O1 180.0 6_565 2_655 ?
O1 Mn2 O1 88.26(8) 2_655 . ?
O1 Mn2 O4 89.11(5) 5_665 . ?
O1 Mn2 O4 90.90(5) 2_655 5_665 ?
O1 Mn2 O4 90.89(5) 6_565 . ?
O1 Mn2 O4 89.11(5) 2_655 . ?
O1 Mn2 O4 89.11(5) . 5_665 ?
O1 Mn2 O4 90.89(5) . . ?
O1 Mn2 O4 90.90(5) 5_665 5_665 ?
O1 Mn2 O4 89.10(5) 6_565 5_665 ?
O4 Mn2 O4 180.0 . 5_665 ?
C12 O1 Mn2 129.62(13) . . ?
Mn1 O3 H3 113.2(19) . 6_575 ?
Mn1 O3 H3 113.2(19) . . ?
H3 O3 H3 115(4) . 6_575 ?
Mn2 O4 H4 102.8(18) . 6_565 ?
Mn2 O4 H4 102.8(18) . . ?
H4 O4 H4 101(3) . 6_565 ?
C4 N1 Mn1 127.01(10) 2_756 . ?
C4 N1 Mn1 127.01(10) . . ?
C4 N1 C4 106.0(2) . 2_756 ?
C2 N2 Mn1 126.78(10) . . ?
C2 N2 Mn1 126.78(10) 6_575 . ?
C2 N2 C2 106.2(2) . 6_575 ?
C1 C1 H1 126.3 6_575 . ?
C1 C1 C2 107.43(11) 6_575 . ?
C2 C1 H1 126.3 . . ?
N2 C2 C1 109.48(17) . . ?
N2 C2 C3 126.25(16) . . ?
C3 C2 C1 124.25(17) . . ?
C2 C3 C4 123.89(16) . . ?
C2 C3 C6 118.40(16) . . ?
C4 C3 C6 117.71(16) . . ?
N1 C4 C3 125.98(16) . . ?
N1 C4 C5 109.41(15) . . ?
C3 C4 C5 124.60(16) . . ?
C4 C5 H5 126.2 . . ?
C5 C5 C4 107.60(10) 2_756 . ?
C5 C5 H5 126.2 2_756 . ?
C7 C6 C3 121.26(19) . . ?
C11 C6 C3 120.69(18) . . ?
C11 C6 C7 118.05(18) . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C12 121.86(18) . . ?
C10 C9 C8 118.28(18) . . ?
C10 C9 C12 119.86(18) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C6 C11 C10 121.1(2) . . ?
C6 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
O1 C12 O2 125.67(17) . . ?
O1 C12 C9 117.21(18) . . ?
O2 C12 C9 117.11(18) . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.019 0.270 -0.003 1448 226 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.736
_oxdiff_exptl_absorpt_empirical_full_min 0.678
