# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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 1590622'
_audit_update_record             
;
2017-12-12 deposited with the CCDC.
2018-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H7 Mn N5 O3'
_chemical_formula_weight         252.11

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.7052(17)
_cell_length_b                   10.349(2)
_cell_length_c                   10.742(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     967.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8891
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      27.58

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    1.359
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2220
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10138
_diffrn_reflns_av_R_equivalents  0.0987
_diffrn_reflns_av_sigmaI/netI    0.0846
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2220
_reflns_number_gt                1732
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0775P)²+0.5448P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.14(6)
_refine_ls_number_reflns         2220
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.1682
_refine_ls_wR_factor_gt          0.1582
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.154
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.69496(11) 1.06144(9) 0.77816(9) 0.0241(3) Uani 1 1 d . . .
N5 N 0.8734(6) 0.8919(5) 0.7833(6) 0.0289(13) Uani 1 1 d . . .
C1 C 0.9004(8) 0.8415(6) 0.6712(6) 0.0238(15) Uani 1 1 d . . .
O1 O 0.7262(6) 0.9938(5) 0.5860(5) 0.0403(13) Uani 1 1 d . . .
N1 N 0.5117(8) 0.9251(7) 0.8203(8) 0.062(2) Uani 1 1 d . . .
C5 C 0.8121(9) 0.9009(6) 0.5626(6) 0.0277(14) Uani 1 1 d . . .
C4 C 0.9511(9) 0.8420(7) 0.8792(6) 0.0337(18) Uani 1 1 d . . .
H4A H 0.9309 0.8713 0.9594 0.040 Uiso 1 1 calc R . .
N2 N 0.4853(6) 0.8143(6) 0.8090(6) 0.0363(15) Uani 1 1 d . . .
O2 O 0.8349(6) 0.8523(5) 0.4567(4) 0.0377(13) Uani 1 1 d . . .
C2 C 1.0105(8) 0.7445(7) 0.6527(6) 0.0305(16) Uani 1 1 d . . .
H2A H 1.0258 0.7117 0.5731 0.037 Uiso 1 1 calc R . .
N4 N 1.0938(6) 0.6981(6) 0.7474(5) 0.0297(15) Uani 1 1 d . . .
C3 C 1.0622(9) 0.7466(7) 0.8610(6) 0.0352(18) Uani 1 1 d . . .
H3A H 1.1162 0.7155 0.9295 0.042 Uiso 1 1 calc R . .
N3 N 0.4567(9) 0.7061(7) 0.8027(7) 0.055(2) Uani 1 1 d . . .
O3 O 0.2154(11) 0.0326(12) 0.6822(17) 0.180(6) Uani 1 1 d . . .
C6 C 0.2587(18) -0.0001(17) 0.5623(15) 0.115(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Mn1 0.0265(4) 0.0191(4) 0.0269(5) 0.0002(4) 0.0004(5) -0.0003(4)
N5 0.031(3) 0.034(3) 0.022(3) -0.005(3) -0.001(3) 0.003(2)
C1 0.028(3) 0.018(3) 0.025(3) 0.001(3) 0.000(3) -0.003(3)
O1 0.049(3) 0.038(3) 0.034(3) 0.000(2) -0.016(2) 0.012(3)
N1 0.052(4) 0.031(4) 0.102(7) -0.011(4) 0.023(4) -0.016(4)
C5 0.032(3) 0.029(4) 0.022(3) -0.002(2) -0.001(3) -0.008(3)
C4 0.043(4) 0.038(4) 0.020(3) -0.003(3) 0.001(3) 0.013(3)
N2 0.033(3) 0.040(4) 0.037(4) 0.006(3) 0.003(3) -0.003(3)
O2 0.054(3) 0.036(3) 0.023(2) -0.002(2) -0.008(2) 0.005(2)
C2 0.041(4) 0.030(4) 0.020(3) -0.005(3) -0.005(3) 0.004(3)
N4 0.038(3) 0.034(3) 0.016(3) 0.003(2) 0.000(2) 0.008(3)
C3 0.047(5) 0.043(5) 0.016(3) 0.006(3) -0.002(3) 0.013(4)
N3 0.076(5) 0.030(4) 0.059(5) 0.008(3) -0.021(4) -0.025(3)
O3 0.075(6) 0.156(11) 0.31(2) -0.003(13) -0.033(10) 0.024(7)
C6 0.111(11) 0.146(13) 0.089(12) 0.017(9) 0.033(8) -0.026(10)

_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 2.131(5) 2_675 ?
Mn1 N1 2.177(7) . ?
Mn1 N3 2.177(7) 3_656 ?
Mn1 O1 2.196(5) . ?
Mn1 N4 2.336(6) 3_756 ?
Mn1 N5 2.344(5) . ?
N5 C1 1.334(9) . ?
N5 C4 1.336(9) . ?
C1 C2 1.402(9) . ?
C1 C5 1.526(9) . ?
O1 C5 1.244(8) . ?
N1 N2 1.176(9) . ?
C5 O2 1.260(8) . ?
C4 C3 1.396(10) . ?
C4 H4A 0.9300 . ?
N2 N3 1.149(8) . ?
O2 Mn1 2.131(5) 2_674 ?
C2 N4 1.339(8) . ?
C2 H2A 0.9300 . ?
N4 C3 1.348(8) . ?
N4 Mn1 2.336(5) 3_746 ?
C3 H3A 0.9300 . ?
N3 Mn1 2.177(7) 3_646 ?
O3 C6 1.38(2) . ?

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 N1 89.7(3) 2_675 . ?
O2 Mn1 N3 89.8(2) 2_675 3_656 ?
N1 Mn1 N3 94.8(3) . 3_656 ?
O2 Mn1 O1 173.83(19) 2_675 . ?
N1 Mn1 O1 94.6(3) . . ?
N3 Mn1 O1 85.4(2) 3_656 . ?
O2 Mn1 N4 87.04(19) 2_675 3_756 ?
N1 Mn1 N4 173.5(3) . 3_756 ?
N3 Mn1 N4 90.8(3) 3_656 3_756 ?
O1 Mn1 N4 89.1(2) . 3_756 ?
O2 Mn1 N5 111.9(2) 2_675 . ?
N1 Mn1 N5 89.7(2) . . ?
N3 Mn1 N5 157.8(2) 3_656 . ?
O1 Mn1 N5 72.6(2) . . ?
N4 Mn1 N5 86.2(2) 3_756 . ?
C1 N5 C4 117.1(6) . . ?
C1 N5 Mn1 112.8(5) . . ?
C4 N5 Mn1 130.0(5) . . ?
N5 C1 C2 121.9(6) . . ?
N5 C1 C5 116.4(6) . . ?
C2 C1 C5 121.7(6) . . ?
C5 O1 Mn1 120.7(4) . . ?
N2 N1 Mn1 138.9(6) . . ?
O1 C5 O2 125.9(6) . . ?
O1 C5 C1 117.4(6) . . ?
O2 C5 C1 116.8(6) . . ?
N5 C4 C3 121.1(6) . . ?
N5 C4 H4A 119.5 . . ?
C3 C4 H4A 119.5 . . ?
N3 N2 N1 177.2(8) . . ?
C5 O2 Mn1 128.8(4) . 2_674 ?
N4 C2 C1 121.3(6) . . ?
N4 C2 H2A 119.3 . . ?
C1 C2 H2A 119.3 . . ?
C2 N4 C3 116.3(6) . . ?
C2 N4 Mn1 123.7(4) . 3_746 ?
C3 N4 Mn1 119.5(4) . 3_746 ?
N4 C3 C4 122.1(6) . . ?
N4 C3 H3A 118.9 . . ?
C4 C3 H3A 118.9 . . ?
N2 N3 Mn1 145.6(6) . 3_646 ?

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
O2 Mn1 N5 C1 -176.3(4) 2_675 . . . ?
N1 Mn1 N5 C1 94.1(5) . . . . ?
N3 Mn1 N5 C1 -8.2(9) 3_656 . . . ?
O1 Mn1 N5 C1 -0.8(4) . . . . ?
N4 Mn1 N5 C1 -91.1(5) 3_756 . . . ?
O2 Mn1 N5 C4 2.3(7) 2_675 . . . ?
N1 Mn1 N5 C4 -87.3(7) . . . . ?
N3 Mn1 N5 C4 170.5(7) 3_656 . . . ?
O1 Mn1 N5 C4 177.9(7) . . . . ?
N4 Mn1 N5 C4 87.6(6) 3_756 . . . ?
C4 N5 C1 C2 -2.8(10) . . . . ?
Mn1 N5 C1 C2 176.0(5) . . . . ?
C4 N5 C1 C5 -179.3(6) . . . . ?
Mn1 N5 C1 C5 -0.4(7) . . . . ?
O2 Mn1 O1 C5 140.3(19) 2_675 . . . ?
N1 Mn1 O1 C5 -86.0(6) . . . . ?
N3 Mn1 O1 C5 179.5(6) 3_656 . . . ?
N4 Mn1 O1 C5 88.6(5) 3_756 . . . ?
N5 Mn1 O1 C5 2.3(5) . . . . ?
O2 Mn1 N1 N2 -137.0(11) 2_675 . . . ?
N3 Mn1 N1 N2 133.2(10) 3_656 . . . ?
O1 Mn1 N1 N2 47.4(11) . . . . ?
N4 Mn1 N1 N2 -77(3) 3_756 . . . ?
N5 Mn1 N1 N2 -25.1(11) . . . . ?
Mn1 O1 C5 O2 178.0(6) . . . . ?
Mn1 O1 C5 C1 -3.2(8) . . . . ?
N5 C1 C5 O1 2.4(9) . . . . ?
C2 C1 C5 O1 -174.1(6) . . . . ?
N5 C1 C5 O2 -178.8(6) . . . . ?
C2 C1 C5 O2 4.8(10) . . . . ?
C1 N5 C4 C3 3.7(11) . . . . ?
Mn1 N5 C4 C3 -174.9(5) . . . . ?
Mn1 N1 N2 N3 142(16) . . . . ?
O1 C5 O2 Mn1 22.8(11) . . . 2_674 ?
C1 C5 O2 Mn1 -156.0(4) . . . 2_674 ?
N5 C1 C2 N4 -0.1(10) . . . . ?
C5 C1 C2 N4 176.1(6) . . . . ?
C1 C2 N4 C3 2.2(10) . . . . ?
C1 C2 N4 Mn1 -169.9(5) . . . 3_746 ?
C2 N4 C3 C4 -1.3(11) . . . . ?
Mn1 N4 C3 C4 171.1(6) 3_746 . . . ?
N5 C4 C3 N4 -1.7(12) . . . . ?
N1 N2 N3 Mn1 103(17) . . . 3_646 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.130
####################################################################### 
# 
# 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 1590623'
_audit_update_record             
;
2017-12-12 deposited with the CCDC.
2018-01-19 downloaded from the CCDC.
;
_audit_creation_date             2017-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 Mn N2 O4, C O'
_chemical_formula_sum            'C7 H8 Mn N2 O5'
_chemical_formula_weight         255.09
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.2234(18)
_cell_length_b                   9.795(2)
_cell_length_c                   10.601(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     957.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8538
_cell_measurement_temperature    293(2)
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.9
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.381
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             516
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2140
_diffrn_reflns_av_unetI/netI     0.1174
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8261
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.927
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                1542
_reflns_number_total             1682
_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    ?
_refine_diff_density_max         2.196
_refine_diff_density_min         -0.900
_refine_diff_density_rms         0.204
_refine_ls_abs_structure_details 
;
 Flack x determined using 499 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1682
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1168
_refine_ls_R_factor_gt           0.1066
_refine_ls_restrained_S_all      1.155
_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)+(0.1213P)²+5.2941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2356
_refine_ls_wR_factor_ref         0.2422
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
: with sigma of 0.1 and sigma for terminal atoms of 0.2
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_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 0.5521(2) 0.5226(2) 0.3044(2) 0.0159(7) Uani 1 1 d . . . . .
N1 N 0.3783(12) 0.5280(13) 0.1317(10) 0.016(2) Uiso 1 1 d . . . . .
C2 C 0.3433(16) 0.4185(14) 0.0832(13) 0.015(3) Uiso 1 1 d . . . . .
N2 N 0.1531(14) 0.4980(11) -0.0590(11) 0.026(3) Uani 1 1 d . . . . .
O3 O 0.7109(13) 0.5745(13) 0.1598(11) 0.041(3) Uani 1 1 d . . . . .
C6 C 0.7463(17) 0.5285(18) 0.0479(14) 0.031(4) Uiso 1 1 d . . . . .
H6 H 0.6974 0.4489 0.0260 0.037 Uiso 1 1 calc R . . . .
O2 O 0.3986(12) 0.1968(9) 0.0941(12) 0.028(3) Uani 1 1 d . . . . .
O4 O 0.8320(14) 0.5690(11) -0.0362(11) 0.037(3) Uani 1 1 d . . . . .
C1 C 0.4303(17) 0.3064(14) 0.1384(13) 0.020(3) Uiso 1 1 d . U . . .
C3 C 0.2329(18) 0.4006(14) -0.0120(15) 0.027(4) Uani 1 1 d . . . . .
H3 H 0.2174 0.3126 -0.0422 0.032 Uiso 1 1 calc R . . . .
C4 C 0.191(2) 0.6112(18) -0.0106(16) 0.035(4) Uiso 1 1 d . U . . .
H4 H 0.1428 0.6892 -0.0377 0.042 Uiso 1 1 calc R . . . .
O1 O 0.5235(10) 0.3286(10) 0.2280(10) 0.024(3) Uani 1 1 d . . . . .
C5 C 0.3023(19) 0.6282(15) 0.0820(17) 0.034(4) Uani 1 1 d . . . . .
H5 H 0.3224 0.7165 0.1091 0.040 Uiso 1 1 calc R . . . .
O5 O -0.037(3) 0.687(3) 0.303(4) 0.170(14) Uani 1 1 d . . . . .
C7 C 0.010(3) 0.817(4) 0.249(4) 0.105(12) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Mn1 0.0157(9) 0.0075(9) 0.0247(11) -0.0014(8) -0.0029(10) 0.0000(8)
N2 0.040(7) 0.007(6) 0.030(6) -0.002(5) -0.014(6) 0.005(5)
O3 0.033(6) 0.043(7) 0.046(7) -0.008(6) 0.023(6) -0.004(5)
O2 0.035(6) 0.004(5) 0.046(7) 0.002(4) -0.010(5) -0.001(4)
O4 0.045(7) 0.017(5) 0.048(7) -0.003(5) 0.024(6) 0.008(5)
C3 0.035(9) 0.006(7) 0.039(9) -0.001(6) 0.000(8) -0.009(6)
O1 0.021(5) 0.013(5) 0.037(7) 0.001(4) -0.007(5) 0.006(4)
C5 0.044(10) 0.005(6) 0.052(10) 0.004(7) -0.033(9) -0.003(6)
O5 0.17(3) 0.10(2) 0.23(4) -0.02(2) -0.09(3) -0.04(2)
C7 0.074(19) 0.10(3) 0.14(3) 0.00(2) 0.00(2) 0.010(18)

_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 N1 2.433(11) . ?
Mn1 N2 2.392(12) 2_565 ?
Mn1 O3 2.181(11) . ?
Mn1 O2 2.068(10) 3_655 ?
Mn1 O4 2.192(11) 2_665 ?
Mn1 O1 2.082(10) . ?
N1 C2 1.232(19) . ?
N1 C5 1.32(2) . ?
C2 C1 1.480(19) . ?
C2 C3 1.44(2) . ?
N2 Mn1 2.392(12) 2_564 ?
N2 C3 1.30(2) . ?
N2 C4 1.27(2) . ?
O3 C6 1.310(19) . ?
C6 O4 1.256(19) . ?
O2 Mn1 2.068(10) 3_645 ?
O2 C1 1.207(17) . ?
O4 Mn1 2.192(11) 2_664 ?
C1 O1 1.299(18) . ?
C4 C5 1.43(2) . ?
O5 C7 1.46(5) . ?

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
N2 Mn1 N1 86.3(4) 2_565 . ?
O3 Mn1 N1 84.8(4) . . ?
O3 Mn1 N2 167.7(4) . 2_565 ?
O3 Mn1 O4 108.0(5) . 2_665 ?
O2 Mn1 N1 121.2(4) 3_655 . ?
O2 Mn1 N2 85.9(4) 3_655 2_565 ?
O2 Mn1 O3 91.5(5) 3_655 . ?
O2 Mn1 O4 80.2(4) 3_655 2_665 ?
O2 Mn1 O1 169.5(4) 3_655 . ?
O4 Mn1 N1 155.5(4) 2_665 . ?
O4 Mn1 N2 83.4(5) 2_665 2_565 ?
O1 Mn1 N1 69.1(4) . . ?
O1 Mn1 N2 93.4(4) . 2_565 ?
O1 Mn1 O3 91.4(5) . . ?
O1 Mn1 O4 89.3(4) . 2_665 ?
C2 N1 Mn1 117.9(9) . . ?
C2 N1 C5 110.0(12) . . ?
C5 N1 Mn1 131.9(10) . . ?
N1 C2 C1 109.8(12) . . ?
N1 C2 C3 125.6(13) . . ?
C3 C2 C1 124.6(12) . . ?
C3 N2 Mn1 128.0(9) . 2_564 ?
C4 N2 Mn1 122.4(11) . 2_564 ?
C4 N2 C3 109.2(13) . . ?
C6 O3 Mn1 136.3(11) . . ?
O4 C6 O3 133.7(16) . . ?
C1 O2 Mn1 118.6(10) . 3_645 ?
C6 O4 Mn1 136.5(11) . 2_664 ?
O2 C1 C2 112.0(13) . . ?
O2 C1 O1 126.4(13) . . ?
O1 C1 C2 121.5(12) . . ?
N2 C3 C2 125.2(13) . . ?
N2 C4 C5 125.3(16) . . ?
C1 O1 Mn1 121.4(8) . . ?
N1 C5 C4 124.7(14) . . ?
