# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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_17ma124_avu-mn-trz
_database_code_depnum_ccdc_archive 'CCDC 1895142'
loop_
_audit_author_name
_audit_author_address
'Juerg Hauser'
;Universit?t Bern
Switzerland
;
_audit_update_record             
;
2019-02-01 deposited with the CCDC.	2019-04-24 downloaded from the CCDC.
;

_audit_creation_date             2017-08-31T22:46:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H16 Mn2 N6 O8'
_chemical_formula_moiety         'C18 H16 Mn2 N6 O8'
_chemical_formula_weight         554.25

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.6208(2)
_cell_length_b                   10.59240(10)
_cell_length_c                   15.2131(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.231(2)
_cell_angle_gamma                90
_cell_volume                     2237.78(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6297
_cell_measurement_theta_min      2.401
_cell_measurement_theta_max      27.723

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.106
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_F_000             1120
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 0 0.0746
1 1 0 0.0626
1 -1 0 0.0526
-1 1 0 0.0536
0 0 -1 0.1484
-1 -1 1 0.0932
0 0 1 0.1786
-1 1 1 0.0944
1 0 0 0.0426
2 -1 -5 0.1498


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.186
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_ambient_temperature      123(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0965
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0309814
_diffrn_orient_matrix_ub_12      0.0532589
_diffrn_orient_matrix_ub_13      -0.0091281
_diffrn_orient_matrix_ub_21      -0.0370585
_diffrn_orient_matrix_ub_22      -0.036895
_diffrn_orient_matrix_ub_23      -0.030372
_diffrn_orient_matrix_ub_31      -0.0166385
_diffrn_orient_matrix_ub_32      -0.0169761
_diffrn_orient_matrix_ub_33      0.0374488
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.035
_diffrn_reflns_number            10803
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.418
_diffrn_reflns_theta_max         28.169
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.929
_reflns_Friedel_coverage         0
_reflns_number_total             2542
_reflns_number_gt                2315
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0287P)²+2.0686P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2542
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.029
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0648
_refine_ls_wR_factor_gt          0.0619
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.42233(10) 0.48336(14) 0.64711(9) 0.0135(3) Uani 1 1 d . . . . .
C2 C 0.45663(10) 0.38535(14) 0.71039(9) 0.0132(3) Uani 1 1 d . . . . .
C3 C 0.38731(12) 0.17302(15) 0.73886(11) 0.0231(3) Uani 1 1 d . . . . .
H3A H 0.321317 0.158801 0.739575 0.035 Uiso 1 1 calc R U . . .
H3B H 0.430539 0.179996 0.802547 0.035 Uiso 1 1 calc R U . . .
H3C H 0.407559 0.102032 0.708007 0.035 Uiso 1 1 calc R U . . .
C4 C 0.26928(11) 0.48381(16) 0.50621(10) 0.0211(3) Uani 1 1 d . . . . .
H4A H 0.267921 0.429638 0.452783 0.025 Uiso 1 1 calc R U . . .
H4B H 0.29062 0.569108 0.494508 0.025 Uiso 1 1 calc R U . . .
C5 C 0.16898(12) 0.4921(2) 0.51432(13) 0.0323(4) Uani 1 1 d . . . . .
H5A H 0.125469 0.530139 0.45798 0.049 Uiso 1 1 calc R U . . .
H5B H 0.170298 0.54437 0.56786 0.049 Uiso 1 1 calc R U . . .
H5C H 0.146183 0.407217 0.522374 0.049 Uiso 1 1 calc R U . . .
C6 C 0.53180(12) 0.81602(15) 0.66769(11) 0.0213(3) Uani 1 1 d . . . . .
C7 C 0.59801(11) 0.58616(14) 0.67876(10) 0.0176(3) Uani 1 1 d . . . . .
C8 C 0.46308(11) 0.67182(14) 0.52746(11) 0.0195(3) Uani 1 1 d . . . . .
C9 C 0.36039(12) 0.72342(15) 0.64502(10) 0.0206(3) Uani 1 1 d . . . . .
Mn1 Mn 0.47869(2) 0.66031(2) 0.64898(2) 0.01384(8) Uani 1 1 d . . . . .
N1 N 0.33872(9) 0.43152(12) 0.59076(8) 0.0157(3) Uani 1 1 d . . . . .
N2 N 0.31823(9) 0.31561(12) 0.61451(9) 0.0187(3) Uani 1 1 d . . . . .
N3 N 0.39108(9) 0.29001(12) 0.68871(8) 0.0154(3) Uani 1 1 d . . . . .
O1 O 0.56396(10) 0.91621(11) 0.67630(9) 0.0326(3) Uani 1 1 d . . . . .
O2 O 0.67254(8) 0.53995(12) 0.69400(8) 0.0249(3) Uani 1 1 d . . . . .
O3 O 0.45628(9) 0.68719(12) 0.45069(8) 0.0299(3) Uani 1 1 d . . . . .
O4 O 0.28569(9) 0.76246(12) 0.64055(9) 0.0316(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.3693(18) . ?
C1 C2 1.398(2) . ?
C1 Mn1 2.0440(15) . ?
C2 N3 1.3599(18) . ?
C2 C2 1.450(3) 2_656 ?
C3 N3 1.4653(19) . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C3 H3C 0.98 . ?
C4 N1 1.4748(18) . ?
C4 C5 1.512(2) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 O1 1.152(2) . ?
C6 Mn1 1.8072(17) . ?
C7 O2 1.1501(19) . ?
C7 Mn1 1.8361(16) . ?
C8 O3 1.1524(19) . ?
C8 Mn1 1.7946(16) . ?
C9 O4 1.150(2) . ?
C9 Mn1 1.8377(16) . ?
Mn1 Mn1 2.9389(4) 2_656 ?
N1 N2 1.3399(17) . ?
N2 N3 1.3153(17) . ?

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 C1 C2 101.01(12) . . ?
N1 C1 Mn1 130.80(11) . . ?
C2 C1 Mn1 127.96(10) . . ?
N3 C2 C1 108.10(12) . . ?
N3 C2 C2 124.62(10) . 2_656 ?
C1 C2 C2 127.17(9) . 2_656 ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C5 111.79(13) . . ?
N1 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O1 C6 Mn1 177.53(15) . . ?
O2 C7 Mn1 177.46(13) . . ?
O3 C8 Mn1 175.24(15) . . ?
O4 C9 Mn1 178.54(15) . . ?
C8 Mn1 C6 90.58(7) . . ?
C8 Mn1 C7 95.05(7) . . ?
C6 Mn1 C7 91.33(7) . . ?
C8 Mn1 C9 97.26(7) . . ?
C6 Mn1 C9 91.53(7) . . ?
C7 Mn1 C9 167.33(7) . . ?
C8 Mn1 C1 97.30(6) . . ?
C6 Mn1 C1 172.11(6) . . ?
C7 Mn1 C1 87.65(6) . . ?
C9 Mn1 C1 87.82(6) . . ?
C8 Mn1 Mn1 173.93(5) . 2_656 ?
C6 Mn1 Mn1 83.98(5) . 2_656 ?
C7 Mn1 Mn1 82.40(5) . 2_656 ?
C9 Mn1 Mn1 85.62(5) . 2_656 ?
C1 Mn1 Mn1 88.12(4) . 2_656 ?
N2 N1 C1 115.45(12) . . ?
N2 N1 C4 115.36(12) . . ?
C1 N1 C4 129.17(13) . . ?
N3 N2 N1 103.36(11) . . ?
N2 N3 C2 112.03(12) . . ?
N2 N3 C3 117.96(12) . . ?
C2 N3 C3 129.81(13) . . ?

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
N1 C1 C2 N3 -2.15(14) . . . . ?
Mn1 C1 C2 N3 172.90(9) . . . . ?
N1 C1 C2 C2 -178.44(16) . . . 2_656 ?
Mn1 C1 C2 C2 -3.4(2) . . . 2_656 ?
C2 C1 N1 N2 1.58(16) . . . . ?
Mn1 C1 N1 N2 -173.26(10) . . . . ?
C2 C1 N1 C4 -176.64(14) . . . . ?
Mn1 C1 N1 C4 8.5(2) . . . . ?
C5 C4 N1 N2 59.00(18) . . . . ?
C5 C4 N1 C1 -122.78(17) . . . . ?
C1 N1 N2 N3 -0.34(16) . . . . ?
C4 N1 N2 N3 178.13(12) . . . . ?
N1 N2 N3 C2 -1.16(16) . . . . ?
N1 N2 N3 C3 174.24(13) . . . . ?
C1 C2 N3 N2 2.20(16) . . . . ?
C2 C2 N3 N2 178.61(15) 2_656 . . . ?
C1 C2 N3 C3 -172.50(14) . . . . ?
C2 C2 N3 C3 3.9(3) 2_656 . . . ?
