# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_Mn-CFA-6
_database_code_depnum_ccdc_archive 'CCDC 1828453'
_audit_update_record             
;
2018-03-08 deposited with the CCDC.
2018-06-04 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         'C6 H5 Mn N4 O, (C4 H9 N O)'
_chemical_formula_sum            'C10 H14 Mn N5 O2'
_chemical_formula_weight         291.20

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      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   12.911(3)
_cell_length_b                   14.712(3)
_cell_length_c                   6.6415(13)
_cell_angle_alpha                90
_cell_angle_beta                 115.41(3)
_cell_angle_gamma                90
_cell_volume                     1139.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    381
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      20.0

_exptl_crystal_description       'block crystal'
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    1.161
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.548498
_exptl_absorpt_correction_T_max  0.745159
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1808
_diffrn_reflns_av_unetI/netI     0.1609
_diffrn_reflns_av_R_equivalents  0.1606
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.769
_diffrn_reflns_theta_max         19.983
_diffrn_reflns_theta_full        19.983
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measured_fraction_theta_full 0.901
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_Laue_measured_fraction_full 0.901
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_point_group_measured_fraction_full 0.901
_reflns_number_total             510
_reflns_number_gt                264
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Diamond 4.4'
_computing_publication_material  Word
_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)+(0.2000P)²] 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         510
_refine_ls_number_parameters     60
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.1899
_refine_ls_R_factor_gt           0.1269
_refine_ls_wR_factor_ref         0.3406
_refine_ls_wR_factor_gt          0.3122
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_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 0.000000 0.000000 0.000000 0.055(3) Uani 1 4 d S T P . .
Mn2 Mn 0.000000 0.000000 0.500000 0.058(3) Uani 1 4 d S TU P . .
O1 O 0.1041(14) 0.000000 0.373(4) 0.067(7) Uani 1 2 d S TU P . .
H1O H 0.185321 0.000000 0.450464 0.080 Uiso 1 2 calc R U P . .
N1 N 0.0937(14) 0.0975(12) -0.058(4) 0.065(5) Uani 1 1 d . U . . .
N2 N 0.0951(14) 0.0981(11) 0.750(3) 0.050(5) Uani 1 1 d . . . . .
C1 C 0.1691(16) 0.1664(13) -0.250(4) 0.056(5) Uani 1 1 d . U . . .
H1 H 0.189534 0.181116 -0.367097 0.067 Uiso 1 1 calc R U . . .
C3 C 0.2075(16) 0.2090(13) -0.044(4) 0.058(5) Uani 1 1 d . U . . .
C2 C 0.1619(16) 0.1643(13) 0.071(4) 0.056(4) Uani 1 1 d . U . . .
H2 H 0.174898 0.177121 0.220346 0.067 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 N1 2.017(19) 5 ?
Mn1 N1 2.017(19) 6 ?
Mn1 N1 2.017(19) 2 ?
Mn1 N1 2.017(19) . ?
Mn1 O1 2.25(2) . ?
Mn1 O1 2.25(2) 5 ?
Mn2 O1 1.87(2) . ?
Mn2 O1 1.87(2) 5_556 ?
Mn2 N2 2.143(17) 5_556 ?
Mn2 N2 2.143(17) 6 ?
Mn2 N2 2.143(17) 2_556 ?
Mn2 N2 2.143(17) . ?
N1 N2 1.29(2) 1_554 ?
N1 C2 1.35(3) . ?
N2 C1 1.39(2) 1_556 ?
C1 C3 1.39(3) . ?
C3 C2 1.32(3) . ?
C3 C3 1.56(4) 7 ?

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
N1 Mn1 N1 89.3(10) 5 6 ?
N1 Mn1 N1 90.7(10) 5 2 ?
N1 Mn1 N1 180.0(15) 6 2 ?
N1 Mn1 N1 180.0 5 . ?
N1 Mn1 N1 90.7(10) 6 . ?
N1 Mn1 N1 89.3(10) 2 . ?
N1 Mn1 O1 85.1(8) 5 . ?
N1 Mn1 O1 94.9(8) 6 . ?
N1 Mn1 O1 85.1(8) 2 . ?
N1 Mn1 O1 94.9(8) . . ?
N1 Mn1 O1 94.9(8) 5 5 ?
N1 Mn1 O1 85.1(8) 6 5 ?
N1 Mn1 O1 94.9(8) 2 5 ?
N1 Mn1 O1 85.1(8) . 5 ?
O1 Mn1 O1 180.0 . 5 ?
O1 Mn2 O1 180.0 . 5_556 ?
O1 Mn2 N2 86.2(7) . 5_556 ?
O1 Mn2 N2 93.8(7) 5_556 5_556 ?
O1 Mn2 N2 93.8(7) . 6 ?
O1 Mn2 N2 86.2(7) 5_556 6 ?
N2 Mn2 N2 95.4(10) 5_556 6 ?
O1 Mn2 N2 86.2(7) . 2_556 ?
O1 Mn2 N2 93.8(7) 5_556 2_556 ?
N2 Mn2 N2 84.6(10) 5_556 2_556 ?
N2 Mn2 N2 180.0 6 2_556 ?
O1 Mn2 N2 93.8(7) . . ?
O1 Mn2 N2 86.2(7) 5_556 . ?
N2 Mn2 N2 180.0 5_556 . ?
N2 Mn2 N2 84.6(10) 6 . ?
N2 Mn2 N2 95.4(10) 2_556 . ?
Mn2 O1 Mn1 106.9(7) . . ?
N2 N1 C2 110.0(19) 1_554 . ?
N2 N1 Mn1 117.3(15) 1_554 . ?
C2 N1 Mn1 133(2) . . ?
N1 N2 C1 107.8(18) 1_556 1_556 ?
N1 N2 Mn2 121.2(14) 1_556 . ?
C1 N2 Mn2 130.9(17) 1_556 . ?
N2 C1 C3 106.5(19) 1_554 . ?
C2 C3 C1 107(2) . . ?
C2 C3 C3 126(3) . 7 ?
C1 C3 C3 128(2) . 7 ?
C3 C2 N1 109(2) . . ?

_refine_diff_density_max         1.674
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.176



