# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_dongxy80
_database_code_depnum_ccdc_archive 'CCDC 2302980'
loop_
_audit_author_name
_audit_author_address
'Xiu-Yan Dong'
;Lanzhou Jiaotong University
China
;
_audit_update_record             
;
2023-10-23 deposited with the CCDC.	2023-11-17 downloaded from the CCDC.
;
_audit_creation_date             2021-07-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H18 Mn N4 O4'
_chemical_formula_sum            'C30 H18 Mn N4 O4'
_chemical_formula_weight         553.42
_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 0.0137 0.0067 '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 -0.0162 2.2332 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   7.9590(6)
_cell_length_b                   10.7872(8)
_cell_length_c                   29.582(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.461(4)
_cell_angle_gamma                90
_cell_volume                     2535.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    193.0
_cell_measurement_theta_max      59.611
_cell_measurement_theta_min      3.796
_shelx_estimated_absorpt_T_max   0.744
_shelx_estimated_absorpt_T_min   0.704
_exptl_absorpt_coefficient_mu    3.146
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1036 before and 0.0710 after correction.
The Ratio of minimum to maximum transmission is 0.8275.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            24117
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.046
_diffrn_reflns_theta_min         3.795
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1993706
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4562
_reflns_number_total             5632
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5632
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0409P)²+0.7458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0943
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
C23A \\sim C22A \\sim N5 \\sim C21A \\sim C20A: within 2A with sigma of 0.005
and sigma for terminal atoms of 0.01 within 2A
Uanis(C23A) \\sim Ueq, Uanis(C22A) \\sim Ueq, Uanis(N5) \\sim Ueq, Uanis(C21A)
\\sim Ueq, Uanis(C20A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
3. Rigid body (RIGU) restrains
 N3, C20, C23, C21, N4, C22, N5, C22A, C21A, C23A, C20A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Sof(N5)=Sof(C22A)=Sof(H22A)=Sof(C21A)=Sof(H21A)=Sof(C23A)=Sof(C20A)=1-FVAR(1)
 Sof(C20)=Sof(C23)=Sof(C21)=Sof(H21)=Sof(N4)=Sof(C22)=Sof(H22)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C19(H19), C16(H16), C26(H26), C28(H28), C29(H29), C1(H1),
 C12(H12), C9(H9), C3(H3), C25(H25), C2(H2), C8(H8), C11(H11), C10(H10),
 C21(H21), C22(H22), C22A(H22A), C21A(H21A)
;
_atom_sites_solution_hydrogens   geom
_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 0.93569(3) 0.11426(2) 0.30045(2) 0.02596(9) Uani 1 1 d . . . . .
O3 O 0.68374(16) 0.17371(12) 0.29817(4) 0.0365(3) Uani 1 1 d . . . . .
O1 O 0.81862(16) 0.91598(13) 0.65817(4) 0.0368(3) Uani 1 1 d . . . . .
O4 O 0.48562(16) 0.24246(12) 0.24810(4) 0.0368(3) Uani 1 1 d . . . . .
O2 O 1.00924(16) 0.79215(12) 0.63178(4) 0.0375(3) Uani 1 1 d . . . . .
N1 N 0.99001(17) -0.05788(14) 0.25835(5) 0.0277(3) Uani 1 1 d . . . . .
N3 N 0.44478(19) 0.62953(14) 0.45025(5) 0.0301(3) Uani 1 1 d . . . . .
N2 N 0.84150(18) -0.05276(14) 0.33787(5) 0.0292(3) Uani 1 1 d . . . . .
C27 C 0.7549(2) 0.82321(16) 0.58637(6) 0.0287(4) Uani 1 1 d . . . . .
C5 C 0.9490(2) -0.16814(16) 0.27702(6) 0.0266(4) Uani 1 1 d . . . . .
C15 C 0.3398(2) 0.38056(15) 0.31659(6) 0.0279(4) Uani 1 1 d . . . . .
H15 H 0.268807 0.361254 0.290569 0.033 Uiso 1 1 calc R U . . .
C14 C 0.4997(2) 0.32884(15) 0.32179(5) 0.0258(4) Uani 1 1 d . . . . .
C18 C 0.5448(2) 0.43595(17) 0.39284(6) 0.0295(4) Uani 1 1 d . . . . .
H18 H 0.615448 0.454608 0.418998 0.035 Uiso 1 1 calc R U . . .
C6 C 0.8712(2) -0.16534(16) 0.31987(6) 0.0272(4) Uani 1 1 d . . . . .
C19 C 0.6011(2) 0.35545(16) 0.36084(6) 0.0288(4) Uani 1 1 d . . . . .
H19 H 0.708930 0.318048 0.365324 0.035 Uiso 1 1 calc R U . . .
C17 C 0.3861(2) 0.49037(16) 0.38747(5) 0.0290(4) Uani 1 1 d . . . . .
C30 C 0.8684(2) 0.84598(17) 0.62781(6) 0.0302(4) Uani 1 1 d . . . . .
C13 C 0.5615(2) 0.24261(16) 0.28690(6) 0.0281(4) Uani 1 1 d . . . . .
C16 C 0.2834(2) 0.45990(17) 0.34907(6) 0.0309(4) Uani 1 1 d . . . . .
H16 H 0.173559 0.494194 0.345253 0.037 Uiso 1 1 calc R U . . .
C4 C 0.9813(2) -0.28298(17) 0.25695(6) 0.0332(4) Uani 1 1 d . . . . .
C7 C 0.8298(2) -0.27653(17) 0.34106(6) 0.0344(4) Uani 1 1 d . . . . .
C26 C 0.5998(3) 0.88087(18) 0.58121(6) 0.0379(5) Uani 1 1 d . . . . .
H26 H 0.571251 0.943187 0.602105 0.045 Uiso 1 1 calc R U . . .
C28 C 0.7987(2) 0.73767(18) 0.55385(6) 0.0339(4) Uani 1 1 d . . . . .
H28 H 0.907938 0.701870 0.555643 0.041 Uiso 1 1 calc R U . . .
C20 C 0.3260(4) 0.5721(3) 0.42300(10) 0.0316(6) Uani 0.874(3) 1 d . . P A 1
C29 C 0.6839(2) 0.70447(19) 0.51893(6) 0.0363(4) Uani 1 1 d . . . . .
H29 H 0.714949 0.645344 0.497138 0.044 Uiso 1 1 calc R U . . .
C1 C 1.0658(2) -0.06010(19) 0.21944(6) 0.0336(4) Uani 1 1 d . . . . .
H1 H 1.096302 0.016438 0.206321 0.040 Uiso 1 1 calc R U . . .
C12 C 0.7711(2) -0.04815(19) 0.37734(6) 0.0372(4) Uani 1 1 d . . . . .
H12 H 0.749521 0.030749 0.390037 0.045 Uiso 1 1 calc R U . . .
C24 C 0.5240(2) 0.75640(18) 0.51529(6) 0.0326(4) Uani 1 1 d . . . . .
C9 C 0.9357(3) -0.39474(17) 0.27907(8) 0.0409(5) Uani 1 1 d . . . . .
H9 H 0.956220 -0.472349 0.265265 0.049 Uiso 1 1 calc R U . . .
C3 C 1.0589(2) -0.2807(2) 0.21533(7) 0.0414(5) Uani 1 1 d . . . . .
H3 H 1.080806 -0.355957 0.200080 0.050 Uiso 1 1 calc R U . . .
C25 C 0.4854(3) 0.8489(2) 0.54596(6) 0.0405(5) Uani 1 1 d . . . . .
H25 H 0.380066 0.890324 0.542648 0.049 Uiso 1 1 calc R U . . .
C2 C 1.1026(2) -0.1699(2) 0.19707(6) 0.0405(5) Uani 1 1 d . . . . .
H2 H 1.157329 -0.167504 0.169430 0.049 Uiso 1 1 calc R U . . .
C23 C 0.3921(4) 0.7013(2) 0.48305(10) 0.0350(7) Uani 0.874(3) 1 d . . P A 1
C8 C 0.8637(3) -0.39186(18) 0.31942(8) 0.0412(5) Uani 1 1 d . . . . .
H8 H 0.835283 -0.467462 0.333552 0.049 Uiso 1 1 calc R U . . .
C11 C 0.7272(3) -0.1537(2) 0.40101(7) 0.0460(5) Uani 1 1 d . . . . .
H11 H 0.677214 -0.146524 0.429249 0.055 Uiso 1 1 calc R U . . .
C10 C 0.7569(3) -0.2673(2) 0.38321(7) 0.0443(5) Uani 1 1 d . . . . .
H10 H 0.728713 -0.340195 0.399121 0.053 Uiso 1 1 calc R U . . .
C21 C 0.1555(3) 0.5908(3) 0.42920(8) 0.0484(7) Uani 0.874(3) 1 d . . P A 1
H21 H 0.074907 0.549706 0.409487 0.058 Uiso 0.874(3) 1 calc R U P A 1
N4 N 0.1008(3) 0.6634(3) 0.46146(8) 0.0654(9) Uani 0.874(3) 1 d . . P A 1
C22 C 0.2197(3) 0.7185(3) 0.48825(9) 0.0573(9) Uani 0.874(3) 1 d . . P A 1
H22 H 0.186144 0.771357 0.511743 0.069 Uiso 0.874(3) 1 calc R U P A 1
N5 N 0.149(2) 0.7661(15) 0.4336(5) 0.055(3) Uani 0.126(3) 1 d . U P A 2
C22A C 0.266(2) 0.8054(18) 0.4660(6) 0.049(3) Uani 0.126(3) 1 d . U P A 2
H22A H 0.246926 0.879980 0.481982 0.058 Uiso 0.126(3) 1 calc R U P A 2
C21A C 0.193(2) 0.6728(19) 0.4081(6) 0.051(3) Uani 0.126(3) 1 d . U P A 2
H21A H 0.118691 0.649261 0.383210 0.061 Uiso 0.126(3) 1 calc R U P A 2
C23A C 0.409(4) 0.741(2) 0.4760(10) 0.044(3) Uani 0.126(3) 1 d . U P A 2
C20A C 0.340(4) 0.608(2) 0.4154(10) 0.048(3) Uani 0.126(3) 1 d . U P A 2


_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 2.1025(13) . ?
Mn1 O1 2.2670(13) 3_766 ?
Mn1 O4 2.1156(12) 2_655 ?
Mn1 O2 2.2638(12) 3_766 ?
Mn1 N1 2.2914(15) . ?
Mn1 N2 2.2658(15) . ?
Mn1 C30 2.5924(17) 3_766 ?
O3 C13 1.254(2) . ?
O1 C30 1.256(2) . ?
O4 C13 1.264(2) . ?
O2 C30 1.262(2) . ?
N1 C5 1.359(2) . ?
N1 C1 1.332(2) . ?
N3 C20 1.354(3) . ?
N3 C23 1.329(3) . ?
N3 C23A 1.46(3) . ?
N3 C20A 1.31(3) . ?
N2 C6 1.353(2) . ?
N2 C12 1.327(2) . ?
C27 C30 1.498(2) . ?
C27 C26 1.383(3) . ?
C27 C28 1.392(2) . ?
C5 C6 1.444(2) . ?
C5 C4 1.404(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.390(2) . ?
C15 C16 1.381(2) . ?
C14 C19 1.399(2) . ?
C14 C13 1.495(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.379(2) . ?
C18 C17 1.393(2) . ?
C6 C7 1.402(2) . ?
C19 H19 0.9500 . ?
C17 C16 1.398(2) . ?
C17 C20 1.474(4) . ?
C17 C20A 1.57(3) . ?
C16 H16 0.9500 . ?
C4 C9 1.429(3) . ?
C4 C3 1.411(3) . ?
C7 C8 1.432(3) . ?
C7 C10 1.410(3) . ?
C26 H26 0.9500 . ?
C26 C25 1.386(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.384(2) . ?
C20 C21 1.395(4) . ?
C29 H29 0.9500 . ?
C29 C24 1.389(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.396(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.392(3) . ?
C24 C25 1.395(3) . ?
C24 C23 1.498(4) . ?
C24 C23A 1.45(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.355(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.365(3) . ?
C25 H25 0.9500 . ?
C2 H2 0.9500 . ?
C23 C22 1.402(4) . ?
C8 H8 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.360(3) . ?
C10 H10 0.9500 . ?
C21 H21 0.9500 . ?
C21 N4 1.328(3) . ?
N4 C22 1.336(3) . ?
C22 H22 0.9500 . ?
N5 C22A 1.36(2) . ?
N5 C21A 1.32(2) . ?
C22A H22A 0.9500 . ?
C22A C23A 1.35(3) . ?
C21A H21A 0.9500 . ?
C21A C20A 1.37(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 Mn1 O1 148.33(5) . 3_766 ?
O3 Mn1 O4 95.73(5) . 2_655 ?
O3 Mn1 O2 91.47(5) . 3_766 ?
O3 Mn1 N1 116.14(5) . . ?
O3 Mn1 N2 85.13(5) . . ?
O3 Mn1 C30 120.07(5) . 3_766 ?
O1 Mn1 N1 89.54(5) 3_766 . ?
O1 Mn1 C30 28.97(5) 3_766 3_766 ?
O4 Mn1 O1 100.34(5) 2_655 3_766 ?
O4 Mn1 O2 105.09(5) 2_655 3_766 ?
O4 Mn1 N1 95.02(5) 2_655 . ?
O4 Mn1 N2 166.33(5) 2_655 . ?
O4 Mn1 C30 105.04(5) 2_655 3_766 ?
O2 Mn1 O1 58.09(4) 3_766 3_766 ?
O2 Mn1 N1 144.08(5) 3_766 . ?
O2 Mn1 N2 88.51(5) 3_766 . ?
O2 Mn1 C30 29.12(5) 3_766 3_766 ?
N1 Mn1 C30 117.07(6) . 3_766 ?
N2 Mn1 O1 85.52(5) . 3_766 ?
N2 Mn1 N1 72.54(5) . . ?
N2 Mn1 C30 86.10(5) . 3_766 ?
C13 O3 Mn1 155.92(13) . . ?
C30 O1 Mn1 90.04(11) . 3_766 ?
C13 O4 Mn1 118.20(11) . 2_655 ?
C30 O2 Mn1 90.04(10) . 3_766 ?
C5 N1 Mn1 115.50(11) . . ?
C1 N1 Mn1 126.48(13) . . ?
C1 N1 C5 117.89(16) . . ?
C23 N3 C20 117.5(2) . . ?
C20A N3 C23A 114.8(18) . . ?
C6 N2 Mn1 116.79(11) . . ?
C12 N2 Mn1 124.76(13) . . ?
C12 N2 C6 118.26(16) . . ?
C26 C27 C30 120.44(16) . . ?
C26 C27 C28 118.73(16) . . ?
C28 C27 C30 120.69(16) . . ?
N1 C5 C6 117.67(15) . . ?
N1 C5 C4 123.07(16) . . ?
C4 C5 C6 119.25(16) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C16 C15 C14 120.35(15) . . ?
C15 C14 C19 119.24(16) . . ?
C15 C14 C13 120.71(15) . . ?
C19 C14 C13 120.02(15) . . ?
C19 C18 H18 119.4 . . ?
C19 C18 C17 121.12(15) . . ?
C17 C18 H18 119.4 . . ?
N2 C6 C5 117.31(15) . . ?
N2 C6 C7 122.73(16) . . ?
C7 C6 C5 119.96(16) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 C14 120.04(16) . . ?
C18 C19 H19 120.0 . . ?
C18 C17 C16 118.38(16) . . ?
C18 C17 C20 120.11(18) . . ?
C18 C17 C20A 121.4(11) . . ?
C16 C17 C20 121.42(19) . . ?
C16 C17 C20A 118.2(10) . . ?
O1 C30 Mn1 60.99(9) . 3_766 ?
O1 C30 O2 121.81(16) . . ?
O1 C30 C27 118.90(16) . . ?
O2 C30 Mn1 60.84(9) . 3_766 ?
O2 C30 C27 119.27(16) . . ?
C27 C30 Mn1 179.88(16) . 3_766 ?
O3 C13 O4 124.13(16) . . ?
O3 C13 C14 117.90(15) . . ?
O4 C13 C14 117.96(15) . . ?
C15 C16 C17 120.82(16) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C5 C4 C9 119.52(18) . . ?
C5 C4 C3 117.04(18) . . ?
C3 C4 C9 123.44(18) . . ?
C6 C7 C8 119.17(18) . . ?
C6 C7 C10 117.10(18) . . ?
C10 C7 C8 123.72(18) . . ?
C27 C26 H26 119.6 . . ?
C27 C26 C25 120.85(17) . . ?
C25 C26 H26 119.6 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.38(17) . . ?
C29 C28 H28 119.8 . . ?
N3 C20 C17 116.9(2) . . ?
N3 C20 C21 120.4(3) . . ?
C21 C20 C17 122.7(2) . . ?
C28 C29 H29 119.5 . . ?
C28 C29 C24 120.92(17) . . ?
C24 C29 H29 119.5 . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 122.93(19) . . ?
C2 C1 H1 118.5 . . ?
N2 C12 H12 118.5 . . ?
N2 C12 C11 122.96(19) . . ?
C11 C12 H12 118.5 . . ?
C29 C24 C25 118.34(16) . . ?
C29 C24 C23 119.54(19) . . ?
C29 C24 C23A 123.3(12) . . ?
C25 C24 C23 121.6(2) . . ?
C25 C24 C23A 116.9(11) . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 121.10(18) . . ?
C8 C9 H9 119.5 . . ?
C4 C3 H3 120.1 . . ?
C2 C3 C4 119.72(18) . . ?
C2 C3 H3 120.1 . . ?
C26 C25 C24 120.46(18) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.32(18) . . ?
C3 C2 H2 120.3 . . ?
N3 C23 C24 117.1(3) . . ?
N3 C23 C22 120.8(3) . . ?
C22 C23 C24 122.0(2) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 120.98(18) . . ?
C9 C8 H8 119.5 . . ?
C12 C11 H11 120.4 . . ?
C10 C11 C12 119.19(19) . . ?
C10 C11 H11 120.4 . . ?
C7 C10 H10 120.1 . . ?
C11 C10 C7 119.75(19) . . ?
C11 C10 H10 120.1 . . ?
C20 C21 H21 118.6 . . ?
N4 C21 C20 122.9(2) . . ?
N4 C21 H21 118.6 . . ?
C21 N4 C22 115.9(2) . . ?
C23 C22 H22 118.7 . . ?
N4 C22 C23 122.6(2) . . ?
N4 C22 H22 118.7 . . ?
C21A N5 C22A 116.5(15) . . ?
N5 C22A H22A 119.2 . . ?
C23A C22A N5 121.6(18) . . ?
C23A C22A H22A 119.2 . . ?
N5 C21A H21A 118.3 . . ?
N5 C21A C20A 123.5(18) . . ?
C20A C21A H21A 118.3 . . ?
C24 C23A N3 112.4(18) . . ?
C22A C23A N3 120(2) . . ?
C22A C23A C24 127(2) . . ?
N3 C20A C17 113(2) . . ?
N3 C20A C21A 122(2) . . ?
C21A C20A C17 124(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
Mn1 O3 C13 O4 76.0(4) . . . . ?
Mn1 O3 C13 C14 -105.0(3) . . . . ?
Mn1 O1 C30 O2 1.78(18) 3_766 . . . ?
Mn1 O1 C30 C27 -179.97(15) 3_766 . . . ?
Mn1 O4 C13 O3 2.0(2) 2_655 . . . ?
Mn1 O4 C13 C14 -176.93(11) 2_655 . . . ?
Mn1 O2 C30 O1 -1.79(18) 3_766 . . . ?
Mn1 O2 C30 C27 179.97(15) 3_766 . . . ?
Mn1 N1 C5 C6 2.16(19) . . . . ?
Mn1 N1 C5 C4 -176.78(13) . . . . ?
Mn1 N1 C1 C2 176.38(13) . . . . ?
Mn1 N2 C6 C5 -4.33(19) . . . . ?
Mn1 N2 C6 C7 175.70(13) . . . . ?
Mn1 N2 C12 C11 -174.62(15) . . . . ?
N1 C5 C6 N2 1.4(2) . . . . ?
N1 C5 C6 C7 -178.62(15) . . . . ?
N1 C5 C4 C9 179.34(16) . . . . ?
N1 C5 C4 C3 -0.4(3) . . . . ?
N1 C1 C2 C3 0.3(3) . . . . ?
N3 C20 C21 N4 -0.4(4) . . . . ?
N3 C23 C22 N4 1.0(5) . . . . ?
N2 C6 C7 C8 179.23(16) . . . . ?
N2 C6 C7 C10 -1.1(3) . . . . ?
N2 C12 C11 C10 -0.2(3) . . . . ?
C27 C26 C25 C24 0.9(3) . . . . ?
C27 C28 C29 C24 0.7(3) . . . . ?
C5 N1 C1 C2 0.8(2) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C5 C6 C7 C10 178.90(16) . . . . ?
C5 C4 C9 C8 -0.8(3) . . . . ?
C5 C4 C3 C2 1.5(3) . . . . ?
C15 C14 C19 C18 -2.5(3) . . . . ?
C15 C14 C13 O3 -161.29(16) . . . . ?
C15 C14 C13 O4 17.7(2) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C18 C17 C16 C15 -1.8(3) . . . . ?
C18 C17 C20 N3 25.2(3) . . . . ?
C18 C17 C20 C21 -154.5(2) . . . . ?
C18 C17 C20A N3 -16(3) . . . . ?
C18 C17 C20A C21A 172.9(19) . . . . ?
C6 N2 C12 C11 0.3(3) . . . . ?
C6 C5 C4 C9 0.4(3) . . . . ?
C6 C5 C4 C3 -179.37(16) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C6 C7 C10 C11 1.2(3) . . . . ?
C19 C14 C13 O3 16.8(2) . . . . ?
C19 C14 C13 O4 -164.17(16) . . . . ?
C19 C18 C17 C16 1.0(3) . . . . ?
C19 C18 C17 C20 177.52(18) . . . . ?
C19 C18 C17 C20A -162.4(13) . . . . ?
C17 C18 C19 C14 1.1(3) . . . . ?
C17 C20 C21 N4 179.3(3) . . . . ?
C30 C27 C26 C25 -171.89(19) . . . . ?
C30 C27 C28 C29 171.10(18) . . . . ?
C13 C14 C19 C18 179.38(16) . . . . ?
C16 C15 C14 C19 1.7(3) . . . . ?
C16 C15 C14 C13 179.82(16) . . . . ?
C16 C17 C20 N3 -158.44(19) . . . . ?
C16 C17 C20 C21 21.8(3) . . . . ?
C16 C17 C20A N3 -179.2(13) . . . . ?
C16 C17 C20A C21A 9(3) . . . . ?
C4 C5 C6 N2 -179.61(15) . . . . ?
C4 C5 C6 C7 0.4(2) . . . . ?
C4 C9 C8 C7 0.5(3) . . . . ?
C4 C3 C2 C1 -1.5(3) . . . . ?
C26 C27 C30 O1 1.6(3) . . . . ?
C26 C27 C30 O2 179.89(18) . . . . ?
C26 C27 C28 C29 -4.7(3) . . . . ?
C28 C27 C30 O1 -174.14(17) . . . . ?
C28 C27 C30 O2 4.2(3) . . . . ?
C28 C27 C26 C25 3.9(3) . . . . ?
C28 C29 C24 C25 4.2(3) . . . . ?
C28 C29 C24 C23 -168.0(2) . . . . ?
C28 C29 C24 C23A 169.8(13) . . . . ?
C20 N3 C23 C24 175.30(19) . . . . ?
C20 N3 C23 C22 -1.5(4) . . . . ?
C20 C17 C16 C15 -178.27(18) . . . . ?
C20 C21 N4 C22 -0.2(5) . . . . ?
C29 C24 C25 C26 -5.0(3) . . . . ?
C29 C24 C23 N3 -19.2(3) . . . . ?
C29 C24 C23 C22 157.6(3) . . . . ?
C29 C24 C23A N3 24(2) . . . . ?
C29 C24 C23A C22A -167(2) . . . . ?
C1 N1 C5 C6 178.24(15) . . . . ?
C1 N1 C5 C4 -0.7(2) . . . . ?
C12 N2 C6 C5 -179.61(16) . . . . ?
C12 N2 C6 C7 0.4(2) . . . . ?
C12 C11 C10 C7 -0.6(3) . . . . ?
C24 C23 C22 N4 -175.7(3) . . . . ?
C9 C4 C3 C2 -178.23(18) . . . . ?
C3 C4 C9 C8 178.93(19) . . . . ?
C25 C24 C23 N3 169.0(2) . . . . ?
C25 C24 C23 C22 -14.3(4) . . . . ?
C25 C24 C23A N3 -170.5(12) . . . . ?
C25 C24 C23A C22A -1(3) . . . . ?
C23 N3 C20 C17 -178.52(19) . . . . ?
C23 N3 C20 C21 1.2(3) . . . . ?
C23 C24 C25 C26 167.0(2) . . . . ?
C8 C7 C10 C11 -179.18(19) . . . . ?
C10 C7 C8 C9 -179.3(2) . . . . ?
C21 N4 C22 C23 -0.1(5) . . . . ?
N5 C22A C23A N3 3(4) . . . . ?
N5 C22A C23A C24 -166(2) . . . . ?
N5 C21A C20A N3 4(4) . . . . ?
N5 C21A C20A C17 175(2) . . . . ?
C22A N5 C21A C20A 6(3) . . . . ?
C21A N5 C22A C23A -10(3) . . . . ?
C23A N3 C20A C17 178.0(16) . . . . ?
C23A N3 C20A C21A -10(3) . . . . ?
C23A C24 C25 C26 -171.5(13) . . . . ?
C20A N3 C23A C24 177.3(18) . . . . ?
C20A N3 C23A C22A 7(3) . . . . ?
C20A C17 C16 C15 162.1(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dongxy87
_database_code_depnum_ccdc_archive 'CCDC 2302981'
loop_
_audit_author_name
_audit_author_address
'Xiu-Yan Dong'
;Lanzhou Jiaotong University
China
;
_audit_update_record             
;
2023-10-23 deposited with the CCDC.	2023-11-17 downloaded from the CCDC.
;
_audit_creation_date             2021-11-28
_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         'C18 H12 Mn N2 O5, C6 H5 N2'
_chemical_formula_sum            'C24 H17 Mn N4 O5'
_chemical_formula_weight         496.35
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.5840(2)
_cell_length_b                   10.5520(3)
_cell_length_c                   11.7635(3)
_cell_angle_alpha                93.8320(10)
_cell_angle_beta                 111.2460(10)
_cell_angle_gamma                108.9600(10)
_cell_volume                     1025.39(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7339
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.02
_cell_measurement_theta_min      5.26
_shelx_estimated_absorpt_T_max   0.383
_shelx_estimated_absorpt_T_min   0.332
_exptl_absorpt_coefficient_mu    5.653
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1092 before and 0.0506 after correction. The Ratio of minimum to maximum transmission is 0.6838. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12217
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.096
_diffrn_reflns_theta_min         5.255
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3729
_reflns_number_total             3960
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         3960
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+0.2807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0786
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups
2. Restrained distances
 O5-H5B = O5-H5A
 0.85 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C16A) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17A) \\sim Ueq, Uanis(C17)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C17A) = Uanis(C17)
Uanis(C16A) = Uanis(C16)
4. Same fragment restrains
{C12, C13A, C14A, C15, C16A, C17A, C7, C10, C16, C6, C19, C18, C17, C22} sigma
for 1-2: 0.02, 1-3: 0.04
as
{C12, C13A, C14A, C15, C16A, C17A, C7, C10, C16, C6, C19, C18, C17, C22}
{C22, C23, C24} sigma for 1-2: 0.02, 1-3: 0.04
as
{C23A, C24A, C24}
5. Others
 Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=1-FVAR(1)
 Sof(C24)=Sof(H24)=Sof(C23)=Sof(H23)=FVAR(1)
 Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=
 Sof(H17A)=1-FVAR(2)
 Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C14)=Sof(H14)=Sof(C13)=Sof(H13)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C13A(H13A), C14A(H14A), C16A(H16A), C17A(H17A),
 C7(H7), C10(H10), C16(H16), C6(H6), C19(H19), C17(H17), C21(H21), C20(H20),
 C23A(H23A), C24A(H24A), C24(H24), C23(H23), C14(H14), C13(H13)
;
_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 1.21385(3) 0.95028(2) 1.03503(2) 0.01671(9) Uani 1 1 d . . . . .
O2 O 0.82151(14) 0.88231(11) 0.88091(11) 0.0210(2) Uani 1 1 d . . . . .
O1 O 0.99200(14) 0.78774(12) 0.98729(12) 0.0251(3) Uani 1 1 d . . . . .
O5 O 1.28243(15) 0.81633(12) 0.93747(13) 0.0257(3) Uani 1 1 d D . . . .
O4 O -0.51133(14) 0.06621(12) 0.14588(12) 0.0238(3) Uani 1 1 d . . . . .
O3 O -0.65147(15) -0.08355(14) 0.22328(14) 0.0360(3) Uani 1 1 d . . . . .
N2 N 0.18406(17) 0.24027(13) 0.70283(13) 0.0194(3) Uani 1 1 d . . . . .
N1 N 0.20194(17) 0.06753(13) 0.87241(13) 0.0183(3) Uani 1 1 d . . . . .
N4 N 0.20043(19) 0.50598(16) 0.34607(14) 0.0258(3) Uani 1 1 d . . . . .
C3 C 0.74449(19) 0.52875(17) 0.91444(15) 0.0198(3) Uani 1 1 d . . . . .
H3 H 0.852501 0.533538 0.952941 0.024 Uiso 1 1 calc R . . . .
N3 N -0.0570(2) 0.42703(17) 0.21635(17) 0.0336(4) Uani 1 1 d . . . . .
C2 C 0.71490(19) 0.64614(16) 0.88676(15) 0.0180(3) Uani 1 1 d . . . . .
C8 C 0.32031(19) 0.26639(16) 0.80334(15) 0.0169(3) Uani 1 1 d . . . . .
C4 C 0.6171(2) 0.40487(16) 0.88607(16) 0.0194(3) Uani 1 1 d . . . . .
H4 H 0.638067 0.325162 0.905476 0.023 Uiso 1 1 calc R . . . .
C5 C 0.45792(19) 0.39677(16) 0.82908(15) 0.0171(3) Uani 1 1 d . . . . .
C1 C 0.8529(2) 0.78214(16) 0.92090(15) 0.0185(3) Uani 1 1 d . . . . .
C9 C 0.3303(2) 0.17775(16) 0.88706(15) 0.0182(3) Uani 1 1 d . . . . .
H9 H 0.430351 0.196420 0.955505 0.022 Uiso 1 1 calc R . . . .
C11 C 0.0563(2) 0.12649(16) 0.68481(16) 0.0188(3) Uani 1 1 d . . . . .
C12 C -0.0927(2) 0.09589(17) 0.57095(17) 0.0227(4) Uani 1 1 d D . . . .
C13A C -0.2437(5) 0.0025(5) 0.5680(5) 0.0189(10) Uani 0.483(9) 1 d D . P A 2
H13A H -0.247646 -0.039062 0.636580 0.023 Uiso 0.483(9) 1 calc R . P A 2
C14A C -0.3815(5) -0.0237(5) 0.4617(5) 0.0205(11) Uani 0.483(9) 1 d D . P A 2
H14A H -0.483319 -0.081392 0.457805 0.025 Uiso 0.483(9) 1 calc R . P A 2
C15 C -0.3716(2) 0.03867(18) 0.35134(19) 0.0283(4) Uani 1 1 d D . . . .
C16A C -0.2290(16) 0.1382(11) 0.3742(14) 0.0184(13) Uani 0.483(9) 1 d D U P A 2
H16A H -0.221681 0.191883 0.313350 0.022 Uiso 0.483(9) 1 calc R . P A 2
C17A C -0.0899(13) 0.1664(10) 0.4843(12) 0.0171(12) Uani 0.483(9) 1 d D U P A 2
H17A H 0.007752 0.238155 0.495650 0.020 Uiso 0.483(9) 1 calc R . P A 2
C7 C 0.5560(2) 0.63742(16) 0.82734(17) 0.0219(3) Uani 1 1 d D . . . .
H7 H 0.535291 0.716832 0.806373 0.026 Uiso 1 1 calc R . . . .
C10 C 0.0657(2) 0.04256(16) 0.77205(16) 0.0191(3) Uani 1 1 d D . . . .
H10 H -0.027755 -0.034674 0.759642 0.023 Uiso 1 1 calc R . . . .
C16 C -0.2390(15) 0.1646(10) 0.3802(13) 0.0184(13) Uani 0.517(9) 1 d D U P A 1
H16 H -0.244166 0.227217 0.325879 0.022 Uiso 0.517(9) 1 calc R . P A 1
C6 C 0.4281(2) 0.51381(16) 0.79865(17) 0.0211(3) Uani 1 1 d D . . . .
H6 H 0.320149 0.508701 0.758316 0.025 Uiso 1 1 calc R . . . .
C19 C 0.0600(2) 0.3954(2) 0.28914(18) 0.0301(4) Uani 1 1 d D . . . .
H19 H 0.048593 0.305079 0.301181 0.036 Uiso 1 1 calc R . . . .
C18 C -0.5206(2) 0.00454(17) 0.23336(19) 0.0263(4) Uani 1 1 d D . . . .
C17 C -0.1044(12) 0.1938(9) 0.4872(11) 0.0171(12) Uani 0.517(9) 1 d D U P A 1
H17 H -0.016476 0.278743 0.508417 0.020 Uiso 0.517(9) 1 calc R . P A 1
C22 C 0.3522(2) 0.50382(19) 0.42535(17) 0.0252(4) Uani 1 1 d D . . . .
C21 C 0.1681(2) 0.6168(2) 0.30293(19) 0.0306(4) Uani 1 1 d . . . . .
H21 H 0.242023 0.709007 0.324336 0.037 Uiso 1 1 calc R . . . .
C20 C 0.0102(2) 0.5669(2) 0.22418(19) 0.0320(4) Uani 1 1 d . . . . .
H20 H -0.046419 0.619860 0.180649 0.038 Uiso 1 1 calc R . . . .
C23A C 0.3586(5) 0.3975(4) 0.4875(4) 0.0315(10) Uani 0.519(5) 1 d D . P B 2
H23A H 0.261465 0.327189 0.479281 0.038 Uiso 0.519(5) 1 calc R . P B 2
C24A C 0.4926(5) 0.6064(4) 0.4380(4) 0.0295(10) Uani 0.519(5) 1 d D . P B 2
H24A H 0.488066 0.679729 0.395945 0.035 Uiso 0.519(5) 1 calc R . P B 2
C24 C 0.4685(5) 0.6191(4) 0.5109(4) 0.0262(10) Uani 0.481(5) 1 d D . P B 1
H24 H 0.447804 0.700773 0.517767 0.031 Uiso 0.481(5) 1 calc R . P B 1
C23 C 0.3834(5) 0.3833(4) 0.4126(4) 0.0257(10) Uani 0.481(5) 1 d D . P B 1
H23 H 0.303547 0.304133 0.351921 0.031 Uiso 0.481(5) 1 calc R . P B 1
C14 C -0.3560(5) -0.0591(5) 0.4149(5) 0.0275(13) Uani 0.517(9) 1 d . . P A 1
H14 H -0.438751 -0.147989 0.386132 0.033 Uiso 0.517(9) 1 calc R . P A 1
C13 C -0.2196(5) -0.0313(5) 0.5227(6) 0.0284(13) Uani 0.517(9) 1 d . . P A 1
H13 H -0.211749 -0.102878 0.566415 0.034 Uiso 0.517(9) 1 calc R . P A 1
H5A H 1.349(3) 0.852(2) 0.906(2) 0.043 Uiso 1 1 d DR . . . .
H5B H 1.220(3) 0.7368(14) 0.894(2) 0.043 Uiso 1 1 d DR . . . .


_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 2.1475(12) 2_777 ?
Mn1 O1 2.1010(12) . ?
Mn1 O5 2.1634(13) . ?
Mn1 O4 2.3104(12) 1_766 ?
Mn1 O3 2.2430(14) 1_766 ?
Mn1 N1 2.3351(14) 1_665 ?
Mn1 C18 2.6115(18) 1_766 ?
O2 C1 1.265(2) . ?
O1 C1 1.257(2) . ?
O5 H5A 0.847(10) . ?
O5 H5B 0.848(10) . ?
O4 C18 1.268(2) . ?
O3 C18 1.253(2) . ?
N2 C8 1.335(2) . ?
N2 C11 1.345(2) . ?
N1 C9 1.337(2) . ?
N1 C10 1.336(2) . ?
N4 C19 1.357(2) . ?
N4 C22 1.424(2) . ?
N4 C21 1.386(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.391(2) . ?
C3 C4 1.386(2) . ?
N3 C19 1.299(3) . ?
N3 C20 1.387(3) . ?
C2 C1 1.508(2) . ?
C2 C7 1.395(2) . ?
C8 C5 1.483(2) . ?
C8 C9 1.402(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(2) . ?
C5 C6 1.396(2) . ?
C9 H9 0.9500 . ?
C11 C12 1.481(2) . ?
C11 C10 1.397(2) . ?
C12 C13A 1.449(4) . ?
C12 C17A 1.305(14) . ?
C12 C17 1.477(12) . ?
C12 C13 1.392(4) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.380(5) . ?
C14A H14A 0.9500 . ?
C14A C15 1.514(5) . ?
C15 C16A 1.344(14) . ?
C15 C16 1.424(12) . ?
C15 C18 1.502(2) . ?
C15 C14 1.330(4) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.407(18) . ?
C17A H17A 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.386(2) . ?
C10 H10 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.362(17) . ?
C6 H6 0.9500 . ?
C19 H19 0.9500 . ?
C17 H17 0.9500 . ?
C22 C23A 1.385(4) . ?
C22 C24A 1.375(4) . ?
C22 C24 1.370(4) . ?
C22 C23 1.408(4) . ?
C21 H21 0.9500 . ?
C21 C20 1.352(3) . ?
C20 H20 0.9500 . ?
C23A H23A 0.9500 . ?
C23A C24A 1.393(6) 2_666 ?
C24A H24A 0.9500 . ?
C24 H24 0.9500 . ?
C24 C23 1.388(6) 2_666 ?
C23 H23 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.379(5) . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Mn1 O5 167.45(5) 2_777 . ?
O2 Mn1 O4 88.12(5) 2_777 1_766 ?
O2 Mn1 O3 91.03(5) 2_777 1_766 ?
O2 Mn1 N1 84.46(5) 2_777 1_665 ?
O2 Mn1 C18 88.78(5) 2_777 1_766 ?
O1 Mn1 O2 102.29(5) . 2_777 ?
O1 Mn1 O5 88.41(5) . . ?
O1 Mn1 O4 154.51(5) . 1_766 ?
O1 Mn1 O3 98.46(5) . 1_766 ?
O1 Mn1 N1 110.07(5) . 1_665 ?
O1 Mn1 C18 126.78(5) . 1_766 ?
O5 Mn1 O4 84.77(5) . 1_766 ?
O5 Mn1 O3 93.88(6) . 1_766 ?
O5 Mn1 N1 85.72(5) . 1_665 ?
O5 Mn1 C18 90.00(6) . 1_766 ?
O4 Mn1 N1 93.90(5) 1_766 1_665 ?
O4 Mn1 C18 29.05(5) 1_766 1_766 ?
O3 Mn1 O4 57.69(5) 1_766 1_766 ?
O3 Mn1 N1 151.43(5) 1_766 1_665 ?
O3 Mn1 C18 28.66(5) 1_766 1_766 ?
N1 Mn1 C18 122.83(6) 1_665 1_766 ?
C1 O2 Mn1 132.31(10) . 2_777 ?
C1 O1 Mn1 128.02(11) . . ?
Mn1 O5 H5A 118.1(18) . . ?
Mn1 O5 H5B 124.8(18) . . ?
H5A O5 H5B 109(2) . . ?
C18 O4 Mn1 88.76(10) . 1_344 ?
C18 O3 Mn1 92.22(11) . 1_344 ?
C8 N2 C11 117.81(14) . . ?
C9 N1 Mn1 118.97(11) . 1_445 ?
C10 N1 Mn1 123.15(11) . 1_445 ?
C10 N1 C9 117.16(14) . . ?
C19 N4 C22 125.96(16) . . ?
C19 N4 C21 106.15(16) . . ?
C21 N4 C22 127.69(16) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C4 C3 C2 120.28(15) . . ?
C19 N3 C20 105.40(17) . . ?
C3 C2 C1 120.58(15) . . ?
C3 C2 C7 119.46(15) . . ?
C7 C2 C1 119.97(14) . . ?
N2 C8 C5 118.17(14) . . ?
N2 C8 C9 121.17(15) . . ?
C9 C8 C5 120.53(15) . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.25(15) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C8 120.87(14) . . ?
C4 C5 C6 119.53(15) . . ?
C6 C5 C8 119.58(15) . . ?
O2 C1 C2 118.25(15) . . ?
O1 C1 O2 124.44(15) . . ?
O1 C1 C2 117.31(15) . . ?
N1 C9 C8 121.27(15) . . ?
N1 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
N2 C11 C12 117.46(15) . . ?
N2 C11 C10 120.41(15) . . ?
C10 C11 C12 122.12(15) . . ?
C13A C12 C11 118.2(2) . . ?
C17A C12 C11 120.0(5) . . ?
C17A C12 C13A 121.2(5) . . ?
C17 C12 C11 120.8(4) . . ?
C13 C12 C11 124.4(2) . . ?
C13 C12 C17 114.0(4) . . ?
C12 C13A H13A 121.3 . . ?
C14A C13A C12 117.4(3) . . ?
C14A C13A H13A 121.3 . . ?
C13A C14A H14A 119.8 . . ?
C13A C14A C15 120.5(3) . . ?
C15 C14A H14A 119.8 . . ?
C16A C15 C14A 115.0(7) . . ?
C16A C15 C18 123.9(7) . . ?
C16 C15 C18 119.5(6) . . ?
C18 C15 C14A 120.4(2) . . ?
C14 C15 C16 120.9(5) . . ?
C14 C15 C18 118.6(2) . . ?
C15 C16A H16A 118.5 . . ?
C15 C16A C17A 122.9(12) . . ?
C17A C16A H16A 118.5 . . ?
C12 C17A C16A 121.2(10) . . ?
C12 C17A H17A 119.4 . . ?
C16A C17A H17A 119.4 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.50(15) . . ?
C6 C7 H7 119.7 . . ?
N1 C10 C11 122.06(15) . . ?
N1 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.8(10) . . ?
C17 C16 H16 120.6 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 119.95(15) . . ?
C7 C6 H6 120.0 . . ?
N4 C19 H19 123.8 . . ?
N3 C19 N4 112.44(17) . . ?
N3 C19 H19 123.8 . . ?
O4 C18 Mn1 62.19(9) . 1_344 ?
O4 C18 C15 119.12(16) . . ?
O3 C18 Mn1 59.12(9) . 1_344 ?
O3 C18 O4 121.25(16) . . ?
O3 C18 C15 119.63(17) . . ?
C15 C18 Mn1 177.02(15) . 1_344 ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.2(9) . . ?
C16 C17 H17 119.4 . . ?
C23A C22 N4 120.2(2) . . ?
C24A C22 N4 119.7(2) . . ?
C24A C22 C23A 120.1(3) . . ?
C24 C22 N4 120.3(2) . . ?
C24 C22 C23 120.3(3) . . ?
C23 C22 N4 119.4(2) . . ?
N4 C21 H21 127.0 . . ?
C20 C21 N4 106.05(17) . . ?
C20 C21 H21 127.0 . . ?
N3 C20 H20 125.0 . . ?
C21 C20 N3 109.94(18) . . ?
C21 C20 H20 125.0 . . ?
C22 C23A H23A 120.0 . . ?
C22 C23A C24A 120.0(3) . 2_666 ?
C24A C23A H23A 120.0 2_666 . ?
C22 C24A C23A 119.9(3) . 2_666 ?
C22 C24A H24A 120.1 . . ?
C23A C24A H24A 120.1 2_666 . ?
C22 C24 H24 120.0 . . ?
C22 C24 C23 120.1(3) . 2_666 ?
C23 C24 H24 120.0 2_666 . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.6(3) 2_666 . ?
C24 C23 H23 120.2 2_666 . ?
C15 C14 H14 120.1 . . ?
C15 C14 C13 119.9(3) . . ?
C13 C14 H14 120.1 . . ?
C12 C13 H13 118.1 . . ?
C14 C13 C12 123.7(3) . . ?
C14 C13 H13 118.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
