# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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 1881040'
loop_
_audit_author_name
_audit_author_address
'Zhong-Yi Li'
;Shangqiu Normal University
China
;
_audit_update_record             
;
2018-11-24 deposited with the CCDC.	2019-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 Mn N4 O9'
_chemical_formula_weight         438.24

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

_space_group_crystal_system      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                   4.7678(5)
_cell_length_b                   11.4567(14)
_cell_length_c                   15.8287(17)
_cell_angle_alpha                96.008(4)
_cell_angle_beta                 95.799(4)
_cell_angle_gamma                91.296(4)
_cell_volume                     854.98(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    6825
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            light-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.833
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6648
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(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            12389
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.995
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2989
_reflns_number_gt                2433
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0398P)²+0.4854P] 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         2989
_refine_ls_number_parameters     261
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.063
_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 1.28928(9) 0.37960(4) 0.95133(3) 0.01703(14) Uani 1 1 d . . . . .
C1 C 0.7099(6) 0.3676(2) 0.82483(17) 0.0203(6) Uani 1 1 d . . . . .
N1 N 0.6018(5) 0.3639(2) 0.66838(15) 0.0293(6) Uani 1 1 d . . . . .
O1 O 0.8823(4) 0.3562(2) 0.88707(13) 0.0382(6) Uani 1 1 d . . . . .
O2 O 0.4498(4) 0.37395(18) 0.82776(12) 0.0278(5) Uani 1 1 d . . . . .
C2 C 0.8233(6) 0.3700(3) 0.73977(18) 0.0341(8) Uani 1 1 d . . . . .
H2A H 0.936114 0.441758 0.740626 0.041 Uiso 1 1 calc R U . . .
H2B H 0.945828 0.304411 0.730900 0.041 Uiso 1 1 calc R U . . .
N2 N 0.2871(6) 0.4517(2) 0.57625(16) 0.0332(6) Uani 1 1 d . . . . .
H2 H 0.231178 0.514131 0.554730 0.040 Uiso 1 1 calc R U . . .
O3 O 0.6191(6) 0.5618(2) 0.66400(18) 0.0628(8) Uani 1 1 d . . . . .
N3 N 1.0915(5) 0.80296(19) 0.82883(14) 0.0203(5) Uani 1 1 d . . . . .
C3 C 0.5107(7) 0.4658(3) 0.6382(2) 0.0351(8) Uani 1 1 d . . . . .
O5 O 1.3298(4) 0.57031(15) 0.95282(12) 0.0193(4) Uani 1 1 d . . . . .
C5 C 0.2394(7) 0.2456(3) 0.58239(19) 0.0283(7) Uani 1 1 d . . . . .
O4 O -0.0611(5) 0.3476(2) 0.49005(15) 0.0425(6) Uani 1 1 d . . . . .
C4 C 0.1414(7) 0.3486(3) 0.54456(19) 0.0282(7) Uani 1 1 d . . . . .
N4 N 0.9051(6) 0.9822(2) 0.87074(17) 0.0361(7) Uani 1 1 d . . . . .
O7 O 1.2465(5) 0.9063(2) 0.95621(15) 0.0433(6) Uani 1 1 d . . . . .
C7 C 0.0855(8) 0.1308(3) 0.5546(2) 0.0466(9) Uani 1 1 d . . . . .
H7A H 0.142249 0.098639 0.500725 0.070 Uiso 1 1 calc R U . . .
H7B H -0.113856 0.142697 0.548705 0.070 Uiso 1 1 calc R U . . .
H7C H 0.129308 0.077359 0.596510 0.070 Uiso 1 1 calc R U . . .
O6 O 0.9089(4) 0.65087(18) 0.93362(12) 0.0247(5) Uani 1 1 d . . . . .
C6 C 0.4596(7) 0.2592(3) 0.64221(19) 0.0301(7) Uani 1 1 d . . . . .
H6 H 0.520063 0.193394 0.667702 0.036 Uiso 1 1 calc R U . . .
O8 O 0.5594(6) 1.0629(2) 0.78891(15) 0.0494(7) Uani 1 1 d . . . . .
C8 C 1.1564(5) 0.6378(2) 0.91810(16) 0.0143(5) Uani 1 1 d . . . . .
C9 C 1.2684(6) 0.7050(2) 0.85059(18) 0.0229(6) Uani 1 1 d . . . . .
H9A H 1.457415 0.735397 0.870943 0.027 Uiso 1 1 calc R U . . .
H9B H 1.280519 0.651624 0.799433 0.027 Uiso 1 1 calc R U . . .
O9 O 1.3526(5) 0.18878(19) 0.93772(14) 0.0326(5) Uani 1 1 d D . . . .
H9C H 1.418(7) 0.161(3) 0.8946(16) 0.039 Uiso 1 1 d D U . . .
H9D H 1.450(7) 0.157(3) 0.9766(17) 0.039 Uiso 1 1 d D U . . .
C10 C 1.0909(6) 0.8967(3) 0.88926(19) 0.0275(7) Uani 1 1 d . . . . .
C11 C 0.7192(7) 0.9806(3) 0.79689(19) 0.0304(7) Uani 1 1 d . . . . .
C12 C 0.7292(6) 0.8787(3) 0.73624(18) 0.0243(6) Uani 1 1 d . . . . .
C13 C 0.9097(6) 0.7948(2) 0.75498(18) 0.0241(6) Uani 1 1 d . . . . .
H13 H 0.912192 0.728023 0.716275 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5352(8) 0.8697(3) 0.6544(2) 0.0397(8) Uani 1 1 d . . . . .
H14A H 0.596617 0.925389 0.618345 0.060 Uiso 1 1 calc R U . . .
H14B H 0.346522 0.886034 0.667182 0.060 Uiso 1 1 calc R U . . .
H14C H 0.538832 0.791755 0.625645 0.060 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 O1 2.096(2) . ?
Mn1 O2 2.167(2) 1_655 ?
Mn1 O5 2.1865(18) . ?
Mn1 O6 2.190(2) 2_767 ?
Mn1 O9 2.205(2) . ?
Mn1 O5 2.2681(18) 2_867 ?
C1 O1 1.237(3) . ?
C1 O2 1.249(3) . ?
C1 C2 1.503(4) . ?
N1 C6 1.368(4) . ?
N1 C3 1.370(4) . ?
N1 C2 1.461(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N2 C3 1.368(4) . ?
N2 C4 1.378(4) . ?
N2 H2 0.8600 . ?
O3 C3 1.217(4) . ?
N3 C10 1.361(4) . ?
N3 C13 1.377(4) . ?
N3 C9 1.467(3) . ?
O5 C8 1.268(3) . ?
C5 C6 1.336(4) . ?
C5 C4 1.444(4) . ?
C5 C7 1.493(4) . ?
O4 C4 1.227(4) . ?
N4 C10 1.370(4) . ?
N4 C11 1.392(4) . ?
O7 C10 1.224(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
O6 C8 1.239(3) . ?
C6 H6 0.9300 . ?
O8 C11 1.234(4) . ?
C8 C9 1.513(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O9 H9C 0.818(18) . ?
O9 H9D 0.850(18) . ?
C11 C12 1.437(4) . ?
C12 C13 1.341(4) . ?
C12 C14 1.506(4) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O2 88.02(8) . 1_655 ?
O1 Mn1 O5 97.89(9) . . ?
O2 Mn1 O5 85.08(8) 1_655 . ?
O1 Mn1 O6 85.91(8) . 2_767 ?
O2 Mn1 O6 168.19(8) 1_655 2_767 ?
O5 Mn1 O6 105.78(8) . 2_767 ?
O1 Mn1 O9 91.56(10) . . ?
O2 Mn1 O9 84.48(8) 1_655 . ?
O5 Mn1 O9 165.65(8) . . ?
O6 Mn1 O9 85.56(8) 2_767 . ?
O1 Mn1 O5 165.29(8) . 2_867 ?
O2 Mn1 O5 104.76(7) 1_655 2_867 ?
O5 Mn1 O5 76.41(7) . 2_867 ?
O6 Mn1 O5 82.72(7) 2_767 2_867 ?
O9 Mn1 O5 96.82(8) . 2_867 ?
O1 C1 O2 124.5(3) . . ?
O1 C1 C2 117.1(2) . . ?
O2 C1 C2 118.3(2) . . ?
C6 N1 C3 120.9(3) . . ?
C6 N1 C2 119.1(3) . . ?
C3 N1 C2 119.2(3) . . ?
C1 O1 Mn1 151.1(2) . . ?
C1 O2 Mn1 118.26(17) . 1_455 ?
N1 C2 C1 113.1(2) . . ?
N1 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C3 N2 C4 127.2(3) . . ?
C3 N2 H2 116.4 . . ?
C4 N2 H2 116.4 . . ?
C10 N3 C13 121.2(2) . . ?
C10 N3 C9 117.0(2) . . ?
C13 N3 C9 121.4(2) . . ?
O3 C3 N2 122.1(3) . . ?
O3 C3 N1 123.0(3) . . ?
N2 C3 N1 114.8(3) . . ?
C8 O5 Mn1 127.56(16) . . ?
C8 O5 Mn1 128.09(16) . 2_867 ?
Mn1 O5 Mn1 103.60(7) . 2_867 ?
C6 C5 C4 117.7(3) . . ?
C6 C5 C7 123.6(3) . . ?
C4 C5 C7 118.6(3) . . ?
O4 C4 N2 121.1(3) . . ?
O4 C4 C5 123.9(3) . . ?
N2 C4 C5 115.0(3) . . ?
C10 N4 C11 125.9(3) . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 O6 Mn1 129.48(16) . 2_767 ?
C5 C6 N1 124.2(3) . . ?
C5 C6 H6 117.9 . . ?
N1 C6 H6 117.9 . . ?
O6 C8 O5 126.0(2) . . ?
O6 C8 C9 118.8(2) . . ?
O5 C8 C9 115.2(2) . . ?
N3 C9 C8 112.9(2) . . ?
N3 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
N3 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
Mn1 O9 H9C 117(3) . . ?
Mn1 O9 H9D 120(2) . . ?
H9C O9 H9D 102(3) . . ?
O7 C10 N3 123.1(3) . . ?
O7 C10 N4 120.9(3) . . ?
N3 C10 N4 115.9(2) . . ?
O8 C11 N4 119.2(3) . . ?
O8 C11 C12 125.5(3) . . ?
N4 C11 C12 115.2(3) . . ?
C13 C12 C11 118.7(3) . . ?
C13 C12 C14 122.5(3) . . ?
C11 C12 C14 118.8(3) . . ?
C12 C13 N3 123.1(3) . . ?
C12 C13 H13 118.5 . . ?
N3 C13 H13 118.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.545
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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 1881041'
loop_
_audit_author_name
_audit_author_address
'Zhong-Yi Li'
;Shangqiu Normal University
China
;
_audit_update_record             
;
2018-11-24 deposited with the CCDC.	2019-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H22 Mn N5 O9.50'
_chemical_formula_weight         503.33

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

_space_group_crystal_system      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                   4.7674(5)
_cell_length_b                   15.2901(14)
_cell_length_c                   15.8525(15)
_cell_angle_alpha                82.467(4)
_cell_angle_beta                 89.755(4)
_cell_angle_gamma                87.662(4)
_cell_volume                     1144.63(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9267
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.635
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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            17546
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.073
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4022
_reflns_number_gt                3406
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0592P)²+0.8795P] 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         4022
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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 0.84107(7) 0.45012(2) 0.59181(2) 0.01991(14) Uani 1 1 d . . . . .
C1 C 0.3010(5) 0.51891(18) 0.69405(16) 0.0271(6) Uani 1 1 d . . . . .
N1 N 0.2133(5) 0.61259(16) 0.80993(14) 0.0325(5) Uani 1 1 d . . . . .
O1 O 0.4699(4) 0.46926(16) 0.66069(15) 0.0459(6) Uani 1 1 d . . . . .
O2 O 0.0436(4) 0.52634(13) 0.67960(12) 0.0331(5) Uani 1 1 d . . . . .
C2 C 0.4239(6) 0.5713(2) 0.7594(2) 0.0394(7) Uani 1 1 d . . . . .
H2A H 0.546276 0.532201 0.797315 0.047 Uiso 1 1 calc R U . . .
H2B H 0.537752 0.616925 0.729973 0.047 Uiso 1 1 calc R U . . .
C16A C 0.743(3) 0.1924(8) 0.7931(7) 0.080(4) Uiso 0.496(17) 1 d . . P A 1
H16A H 0.715953 0.194914 0.732813 0.120 Uiso 0.496(17) 1 calc R U P A 1
H16B H 0.569241 0.178884 0.821879 0.120 Uiso 0.496(17) 1 calc R U P A 1
H16C H 0.883264 0.147380 0.811871 0.120 Uiso 0.496(17) 1 calc R U P A 1
C17A C 0.927(4) 0.2873(8) 0.9029(8) 0.091(4) Uiso 0.496(17) 1 d . . P A 1
H17A H 1.117746 0.304667 0.902996 0.137 Uiso 0.496(17) 1 calc R U P A 1
H17B H 0.910962 0.230966 0.936874 0.137 Uiso 0.496(17) 1 calc R U P A 1
H17C H 0.807797 0.330477 0.925989 0.137 Uiso 0.496(17) 1 calc R U P A 1
C16B C 0.606(5) 0.2435(17) 0.7815(14) 0.183(9) Uiso 0.504(17) 1 d . . P A 2
H16D H 0.587847 0.263271 0.721729 0.275 Uiso 0.504(17) 1 calc R U P A 2
H16E H 0.440231 0.261145 0.810490 0.275 Uiso 0.504(17) 1 calc R U P A 2
H16F H 0.630644 0.180366 0.790572 0.275 Uiso 0.504(17) 1 calc R U P A 2
C17B C 0.771(3) 0.2990(7) 0.8979(7) 0.081(3) Uiso 0.504(17) 1 d . . P A 2
H17D H 0.872479 0.348855 0.910093 0.121 Uiso 0.504(17) 1 calc R U P A 2
H17E H 0.824117 0.248404 0.937978 0.121 Uiso 0.504(17) 1 calc R U P A 2
H17F H 0.573314 0.311770 0.902176 0.121 Uiso 0.504(17) 1 calc R U P A 2
N2 N -0.0850(6) 0.60752(16) 0.92559(15) 0.0380(6) Uani 1 1 d . . . . .
H2 H -0.145320 0.579046 0.972074 0.046 Uiso 1 1 calc R U . . .
O3 O 0.2131(6) 0.49071(15) 0.90916(15) 0.0542(7) Uani 1 1 d . . . . .
N3 N 0.6261(4) 0.80007(13) 0.49118(14) 0.0236(5) Uani 1 1 d . . . . .
C3 C 0.1202(7) 0.56562(19) 0.88310(18) 0.0351(7) Uani 1 1 d . . . . .
O5 O 0.8077(3) 0.56767(10) 0.49892(11) 0.0218(4) Uani 1 1 d . . . . .
N5 N 0.8372(9) 0.2808(2) 0.8131(2) 0.0700(10) Uani 1 1 d . . . . .
C5 C -0.1026(7) 0.7361(2) 0.82243(19) 0.0406(7) Uani 1 1 d . . . . .
O4 O -0.3855(6) 0.72073(17) 0.94622(16) 0.0649(8) Uani 1 1 d . . . . .
N4 N 0.2708(5) 0.90459(13) 0.50601(14) 0.0258(5) Uani 1 1 d . . . . .
H4 H 0.133268 0.923066 0.535145 0.031 Uiso 1 1 calc R U . . .
C4 C -0.2054(7) 0.6911(2) 0.90137(19) 0.0401(7) Uani 1 1 d . . . . .
O6 O 0.3952(4) 0.64104(11) 0.47449(12) 0.0270(4) Uani 1 1 d . . . . .
C6 C 0.0971(7) 0.6950(2) 0.78095(18) 0.0396(7) Uani 1 1 d . . . . .
H6 H 0.161345 0.723626 0.729544 0.047 Uiso 1 1 calc R U . . .
O7 O 0.3614(4) 0.79180(13) 0.61197(13) 0.0366(5) Uani 1 1 d . . . . .
C7 C -0.2231(10) 0.8267(2) 0.7900(3) 0.0670(12) Uani 1 1 d . . . . .
H7A H -0.156725 0.844141 0.733318 0.100 Uiso 1 1 calc R U . . .
H7B H -0.165144 0.868046 0.826510 0.100 Uiso 1 1 calc R U . . .
H7C H -0.424276 0.825693 0.789652 0.100 Uiso 1 1 calc R U . . .
O9 O 0.9551(5) 0.32740(14) 0.67735(14) 0.0485(6) Uani 1 1 d . . . . .
C9 C 0.7813(5) 0.71715(16) 0.52034(18) 0.0259(6) Uani 1 1 d . . . . .
H9A H 0.797391 0.710747 0.581841 0.031 Uiso 1 1 calc R U . . .
H9B H 0.969590 0.719854 0.496953 0.031 Uiso 1 1 calc R U . . .
O8 O 0.1793(4) 1.02164(13) 0.40554(14) 0.0382(5) Uani 1 1 d . . . . .
C8 C 0.6442(5) 0.63646(15) 0.49499(15) 0.0182(5) Uani 1 1 d . . . . .
C10 C 0.4165(5) 0.82913(16) 0.54202(17) 0.0241(6) Uani 1 1 d . . . . .
O10 O -0.500000 1.000000 1.000000 0.80(3) Uani 1 2 d S . P . .
C11 C 0.3213(5) 0.95362(16) 0.42848(18) 0.0258(6) Uani 1 1 d . . . . .
C12 C 0.5445(6) 0.91944(18) 0.37895(18) 0.0307(6) Uani 1 1 d . . . . .
C13 C 0.6817(6) 0.84446(17) 0.41235(18) 0.0291(6) Uani 1 1 d . . . . .
H13 H 0.822841 0.821278 0.380104 0.035 Uiso 1 1 calc R U . . .
C14 C 0.6159(8) 0.9700(2) 0.2943(2) 0.0517(9) Uani 1 1 d . . . . .
H14A H 0.773046 0.940947 0.270009 0.078 Uiso 1 1 calc R U . . .
H14B H 0.662925 1.028850 0.301977 0.078 Uiso 1 1 calc R U . . .
H14C H 0.457260 0.972318 0.256847 0.078 Uiso 1 1 calc R U . . .
C15 C 0.9508(12) 0.3319(3) 0.7543(3) 0.0811(15) Uani 1 1 d . . . . .
H15 H 1.043091 0.378861 0.771682 0.097 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 O1 2.106(2) . ?
Mn1 O5 2.1700(17) . ?
Mn1 O2 2.1808(19) 1_655 ?
Mn1 O6 2.1999(18) 2_666 ?
Mn1 O9 2.216(2) . ?
Mn1 O5 2.2340(17) 2_766 ?
C1 O2 1.247(3) . ?
C1 O1 1.247(3) . ?
C1 C2 1.523(4) . ?
N1 C3 1.364(4) . ?
N1 C6 1.378(4) . ?
N1 C2 1.457(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C16A N5 1.514(11) . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C17A N5 1.504(13) . ?
C17A H17A 0.9600 . ?
C17A H17B 0.9600 . ?
C17A H17C 0.9600 . ?
C16B N5 1.38(2) . ?
C16B H16D 0.9600 . ?
C16B H16E 0.9600 . ?
C16B H16F 0.9600 . ?
C17B N5 1.439(11) . ?
C17B H17D 0.9600 . ?
C17B H17E 0.9600 . ?
C17B H17F 0.9600 . ?
N2 C3 1.370(4) . ?
N2 C4 1.387(4) . ?
N2 H2 0.8600 . ?
O3 C3 1.231(4) . ?
N3 C13 1.372(4) . ?
N3 C10 1.377(3) . ?
N3 C9 1.463(3) . ?
O5 C8 1.278(3) . ?
N5 C15 1.269(5) . ?
C5 C6 1.338(5) . ?
C5 C4 1.441(4) . ?
C5 C7 1.504(5) . ?
O4 C4 1.223(4) . ?
N4 C11 1.379(3) . ?
N4 C10 1.380(3) . ?
N4 H4 0.8600 . ?
O6 C8 1.229(3) . ?
C6 H6 0.9300 . ?
O7 C10 1.212(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
O9 C15 1.231(5) . ?
C9 C8 1.519(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O8 C11 1.232(3) . ?
C11 C12 1.441(4) . ?
C12 C13 1.344(4) . ?
C12 C14 1.503(4) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 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
O1 Mn1 O5 99.08(8) . . ?
O1 Mn1 O2 86.34(8) . 1_655 ?
O5 Mn1 O2 89.38(7) . 1_655 ?
O1 Mn1 O6 86.43(8) . 2_666 ?
O5 Mn1 O6 99.92(7) . 2_666 ?
O2 Mn1 O6 169.02(7) 1_655 2_666 ?
O1 Mn1 O9 91.38(10) . . ?
O5 Mn1 O9 169.37(8) . . ?
O2 Mn1 O9 89.40(8) 1_655 . ?
O6 Mn1 O9 82.51(8) 2_666 . ?
O1 Mn1 O5 171.18(8) . 2_766 ?
O5 Mn1 O5 75.77(6) . 2_766 ?
O2 Mn1 O5 100.62(7) 1_655 2_766 ?
O6 Mn1 O5 87.41(7) 2_666 2_766 ?
O9 Mn1 O5 94.08(8) . 2_766 ?
O2 C1 O1 125.1(2) . . ?
O2 C1 C2 118.9(2) . . ?
O1 C1 C2 116.0(2) . . ?
C3 N1 C6 120.9(3) . . ?
C3 N1 C2 118.7(3) . . ?
C6 N1 C2 120.2(3) . . ?
C1 O1 Mn1 150.3(2) . . ?
C1 O2 Mn1 122.16(17) . 1_455 ?
N1 C2 C1 113.8(2) . . ?
N1 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
N1 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
N5 C16A H16A 109.5 . . ?
N5 C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
N5 C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
N5 C17A H17A 109.5 . . ?
N5 C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
N5 C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
N5 C16B H16D 109.5 . . ?
N5 C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
N5 C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
N5 C17B H17D 109.5 . . ?
N5 C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
N5 C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C3 N2 C4 126.7(3) . . ?
C3 N2 H2 116.6 . . ?
C4 N2 H2 116.6 . . ?
C13 N3 C10 121.5(2) . . ?
C13 N3 C9 119.5(2) . . ?
C10 N3 C9 118.8(2) . . ?
O3 C3 N1 122.5(3) . . ?
O3 C3 N2 122.2(3) . . ?
N1 C3 N2 115.3(3) . . ?
C8 O5 Mn1 131.25(15) . . ?
C8 O5 Mn1 124.39(15) . 2_766 ?
Mn1 O5 Mn1 104.23(6) . 2_766 ?
C15 N5 C16B 110.0(10) . . ?
C15 N5 C17B 127.1(6) . . ?
C16B N5 C17B 107.9(12) . . ?
C15 N5 C17A 117.0(6) . . ?
C15 N5 C16A 118.4(5) . . ?
C17A N5 C16A 117.8(7) . . ?
C6 C5 C4 118.1(3) . . ?
C6 C5 C7 122.8(3) . . ?
C4 C5 C7 119.1(3) . . ?
C11 N4 C10 127.2(2) . . ?
C11 N4 H4 116.4 . . ?
C10 N4 H4 116.4 . . ?
O4 C4 N2 119.7(3) . . ?
O4 C4 C5 125.3(3) . . ?
N2 C4 C5 115.1(3) . . ?
C8 O6 Mn1 129.03(15) . 2_666 ?
C5 C6 N1 123.8(3) . . ?
C5 C6 H6 118.1 . . ?
N1 C6 H6 118.1 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C15 O9 Mn1 116.9(3) . . ?
N3 C9 C8 113.3(2) . . ?
N3 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
N3 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
O6 C8 O5 125.9(2) . . ?
O6 C8 C9 119.9(2) . . ?
O5 C8 C9 114.2(2) . . ?
O7 C10 N3 123.4(2) . . ?
O7 C10 N4 122.5(2) . . ?
N3 C10 N4 114.1(2) . . ?
O8 C11 N4 120.1(2) . . ?
O8 C11 C12 124.3(3) . . ?
N4 C11 C12 115.6(2) . . ?
C13 C12 C11 117.6(3) . . ?
C13 C12 C14 123.6(3) . . ?
C11 C12 C14 118.8(2) . . ?
C12 C13 N3 123.9(2) . . ?
C12 C13 H13 118.0 . . ?
N3 C13 H13 118.0 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 N5 128.6(4) . . ?
O9 C15 H15 115.7 . . ?
N5 C15 H15 115.7 . . ?

_refine_diff_density_max         0.510
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.069

