# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_antoninmnpc3
_database_code_depnum_ccdc_archive 'CCDC 1571877'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-10-23 downloaded from the CCDC.
;

_audit_creation_date             2016-07-22T14:34:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_moiety         'C26 H14 Mn N2 O8, 5 H2 O'
_chemical_formula_sum            'C26 H24 Mn N2 O13'
_chemical_formula_weight         627.41

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.4605(8)
_cell_length_b                   10.4594(5)
_cell_length_c                   18.7370(10)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 111.925(7)
_cell_angle_gamma                90.000(5)
_cell_volume                     2629.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    4306
_cell_measurement_theta_min      4.875
_cell_measurement_theta_max      75.688

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

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.042
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1292
_exptl_absorpt_coefficient_mu    4.755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55219
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

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

_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.199
_diffrn_reflns_number            10673
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         76.51
_diffrn_reflns_theta_full        74
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.981
_reflns_number_total             5298
_reflns_number_gt                3988
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_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)+(0.1499P)²+0.0000P] 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_number_reflns         5298
_refine_ls_number_parameters     399
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0718
_refine_ls_wR_factor_gt          0.1933
_refine_ls_wR_factor_ref         0.2087
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         1.176
_refine_diff_density_min         -0.759

#------------------ 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 0.0181 0.0091 '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'
N N 0.0311 0.018 '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'
Mn Mn -0.5299 2.8052 '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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.6943(3) 0.4792(4) 0.8926(3) 0.0337(9) Uani 1 d . . .
H1 H 0.6854 0.4134 0.9228 0.04 Uiso 1 calc R . .
C2 C 0.7791(3) 0.4835(5) 0.8765(3) 0.0364(9) Uani 1 d . . .
H2 H 0.8277 0.4207 0.8956 0.044 Uiso 1 calc R . .
C3 C 0.7924(3) 0.5820(5) 0.8315(2) 0.0327(9) Uani 1 d . . .
C4 C 0.7174(3) 0.6746(5) 0.8033(2) 0.0340(9) Uani 1 d . . .
H4 H 0.7246 0.7412 0.7729 0.041 Uiso 1 calc R . .
C5 C 0.6335(3) 0.6667(4) 0.8206(2) 0.0322(8) Uani 1 d . . .
H5 H 0.5836 0.7279 0.8019 0.039 Uiso 1 calc R . .
C6 C 0.8816(3) 0.5886(5) 0.8103(3) 0.0342(9) Uani 1 d . . .
C7 C 0.9706(5) 0.5379(12) 0.8551(5) 0.123(5) Uani 1 d . . .
H7 H 0.9772 0.498 0.9011 0.148 Uiso 1 calc R . .
C8 C 1.0518(4) 0.5449(11) 0.8330(4) 0.108(4) Uani 1 d . . .
H8 H 1.112 0.5085 0.8643 0.13 Uiso 1 calc R . .
C9 C 0.8779(5) 0.6478(10) 0.7447(4) 0.092(3) Uani 1 d . . .
H9 H 0.819 0.6869 0.7132 0.11 Uiso 1 calc R . .
C10 C 0.9598(5) 0.6506(11) 0.7245(4) 0.094(3) Uani 1 d . . .
H10 H 0.955 0.688 0.6782 0.113 Uiso 1 calc R . .
C11 C 0.5360(3) 0.5669(4) 0.8852(2) 0.0258(7) Uani 1 d . . .
C12 C 0.4797(3) 0.4568(4) 0.8720(2) 0.0252(7) Uani 1 d . . .
H12 H 0.496 0.3864 0.8488 0.03 Uiso 1 calc R . .
C13 C 0.3976(3) 0.4532(3) 0.8943(2) 0.0228(7) Uani 1 d . . .
C14 C 0.3746(2) 0.5600(4) 0.9284(2) 0.0234(7) Uani 1 d . . .
H14 H 0.3191 0.5582 0.9422 0.028 Uiso 1 calc R . .
C15 C 0.4332(3) 0.6702(4) 0.9423(2) 0.0231(7) Uani 1 d . . .
C16 C 0.5144(3) 0.6742(4) 0.9188(2) 0.0248(7) Uani 1 d . . .
H16 H 0.5528 0.7478 0.9256 0.03 Uiso 1 calc R . .
C17 C 0.3394(3) 0.3320(4) 0.8865(2) 0.0279(8) Uani 1 d . . .
C18 C 0.4116(3) 0.7809(4) 0.9852(2) 0.0259(7) Uani 1 d . . .
C19 C 1.1316(3) 0.6104(4) 0.7473(2) 0.0332(9) Uani 1 d . . .
C20 C 1.1409(3) 0.5235(5) 0.6954(3) 0.0360(9) Uani 1 d . . .
H20 H 1.0962 0.4559 0.6782 0.043 Uiso 1 calc R . .
C21 C 1.2185(3) 0.5384(4) 0.6688(2) 0.0310(8) Uani 1 d . . .
C22 C 1.2857(3) 0.6387(4) 0.6971(2) 0.0288(8) Uani 1 d . . .
H22 H 1.3384 0.648 0.6805 0.035 Uiso 1 calc R . .
C23 C 1.2749(3) 0.7253(4) 0.7499(2) 0.0261(7) Uani 1 d . . .
C24 C 1.1959(3) 0.7115(4) 0.7755(2) 0.0292(8) Uani 1 d . . .
H24 H 1.1873 0.7688 0.8104 0.035 Uiso 1 calc R . .
C25 C 1.2250(3) 0.4488(4) 0.6078(2) 0.0330(9) Uani 1 d . . .
C26 C 1.3467(3) 0.8346(4) 0.7799(2) 0.0264(8) Uani 1 d . . .
N1 N 0.6232(2) 0.5707(3) 0.86474(19) 0.0276(7) Uani 1 d . . .
N2 N 1.0458(2) 0.6005(4) 0.7703(2) 0.0340(8) Uani 1 d . . .
O1 O 0.3748(2) 0.2349(3) 0.86500(16) 0.0313(6) Uani 1 d . . .
O2 O 0.2634(2) 0.3327(3) 0.9024(2) 0.0385(7) Uani 1 d . . .
O3 O 0.3482(2) 0.7679(3) 1.01401(19) 0.0350(7) Uani 1 d . . .
O4 O 0.4640(2) 0.8821(3) 0.98955(15) 0.0277(6) Uani 1 d . . .
O5 O 1.1511(2) 0.3765(4) 0.5762(2) 0.0462(8) Uani 1 d . . .
O6 O 1.3016(2) 0.4490(3) 0.59199(19) 0.0392(7) Uani 1 d . . .
O7 O 1.4200(2) 0.8409(3) 0.75987(17) 0.0325(6) Uani 1 d . . .
O8 O 1.3254(2) 0.9127(3) 0.82327(16) 0.0293(6) Uani 1 d . . .
O9 O 0.5125(2) 0.0391(3) 0.84539(17) 0.0320(6) Uani 1 d . . .
H9A H 0.4915 -0.0249 0.8168 0.048 Uiso 1 d R . .
H9B H 0.5708 0.0113 0.8644 0.048 Uiso 1 d R . .
O10 O 0.2877(2) 0.0743(3) 0.94564(18) 0.0346(6) Uani 1 d . . .
H10A H 0.303 0.0659 0.9941 0.052 Uiso 1 d R . .
H10B H 0.2669 0.151 0.9346 0.052 Uiso 1 d R . .
O11 O 1.1018(5) 0.9267(7) 0.8658(4) 0.109(2) Uani 1 d D . .
O12 O 1.1280(8) 0.1808(11) 0.4750(6) 0.098(5) Uani 0.5 d P . .
O13 O 0.8524(5) 0.2685(10) 1.0241(9) 0.115(5) Uani 0.5 d P . .
O14 O 0.9593(14) 0.2727(14) 0.9270(12) 0.142(6) Uani 0.5 d P . .
O15 O 1.0216(10) 1.0054(19) 0.9577(8) 0.142(6) Uani 0.5 d PD . .
Mn1 Mn 0.41512(4) 0.04446(6) 0.90931(3) 0.0240(2) Uani 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 1.358(6) . ?
C1 C2 1.369(6) . ?
C1 H1 0.93 . ?
C2 C3 1.390(6) . ?
C2 H2 0.93 . ?
C3 C4 1.401(6) . ?
C3 C6 1.486(5) . ?
C4 C5 1.371(5) . ?
C4 H4 0.93 . ?
C5 N1 1.344(5) . ?
C5 H5 0.93 . ?
C6 C7 1.355(8) . ?
C6 C9 1.358(8) . ?
C7 C8 1.385(7) . ?
C7 H7 0.93 . ?
C8 N2 1.285(7) . ?
C8 H8 0.93 . ?
C9 C10 1.374(7) . ?
C9 H9 0.93 . ?
C10 N2 1.327(8) . ?
C10 H10 0.93 . ?
C11 C12 1.378(5) . ?
C11 C16 1.378(5) . ?
C11 N1 1.450(4) . ?
C12 C13 1.399(5) . ?
C12 H12 0.93 . ?
C13 C14 1.387(5) . ?
C13 C17 1.498(5) . ?
C14 C15 1.397(5) . ?
C14 H14 0.93 . ?
C15 C16 1.399(5) . ?
C15 C18 1.507(5) . ?
C16 H16 0.93 . ?
C17 O2 1.242(5) . ?
C17 O1 1.269(5) . ?
C18 O3 1.233(5) . ?
C18 O4 1.287(5) . ?
C19 C20 1.374(6) . ?
C19 C24 1.377(6) . ?
C19 N2 1.460(5) . ?
C20 C21 1.397(5) . ?
C20 H20 0.93 . ?
C21 C22 1.393(6) . ?
C21 C25 1.508(6) . ?
C22 C23 1.393(6) . ?
C22 H22 0.93 . ?
C23 C24 1.401(5) . ?
C23 C26 1.506(5) . ?
C24 H24 0.93 . ?
C25 O6 1.248(5) . ?
C25 O5 1.261(5) . ?
C26 O7 1.251(4) . ?
C26 O8 1.268(5) . ?
O1 Mn1 2.153(3) . ?
O4 Mn1 2.183(3) 3_667 ?
O4 Mn1 2.202(3) 1_565 ?
O8 Mn1 2.149(3) 1_665 ?
O9 Mn1 2.163(3) . ?
O9 H9A 0.84 . ?
O9 H9B 0.8357 . ?
O10 Mn1 2.212(3) . ?
O10 H10A 0.8545 . ?
O10 H10B 0.8547 . ?
Mn1 O8 2.149(3) 1_445 ?
Mn1 O4 2.183(3) 3_667 ?
Mn1 O4 2.202(3) 1_545 ?

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 120.2(4) . . ?
N1 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C1 C2 C3 119.8(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 118.6(4) . . ?
C2 C3 C6 121.8(4) . . ?
C4 C3 C6 119.6(4) . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C5 C4 120.1(4) . . ?
N1 C5 H5 120 . . ?
C4 C5 H5 120 . . ?
C7 C6 C9 116.5(4) . . ?
C7 C6 C3 122.4(4) . . ?
C9 C6 C3 121.1(4) . . ?
C6 C7 C8 120.6(6) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
N2 C8 C7 121.5(6) . . ?
N2 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C6 C9 C10 120.9(6) . . ?
C6 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
N2 C10 C9 120.6(6) . . ?
N2 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C16 122.9(3) . . ?
C12 C11 N1 119.3(3) . . ?
C16 C11 N1 117.8(3) . . ?
C11 C12 C13 118.7(3) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 C17 120.2(3) . . ?
C12 C13 C17 120.1(3) . . ?
C13 C14 C15 121.1(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C16 119.2(3) . . ?
C14 C15 C18 120.0(3) . . ?
C16 C15 C18 120.7(3) . . ?
C11 C16 C15 118.6(3) . . ?
C11 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
O2 C17 O1 125.4(4) . . ?
O2 C17 C13 119.1(3) . . ?
O1 C17 C13 115.5(3) . . ?
O3 C18 O4 125.4(4) . . ?
O3 C18 C15 119.1(3) . . ?
O4 C18 C15 115.5(3) . . ?
C20 C19 C24 123.3(4) . . ?
C20 C19 N2 118.7(4) . . ?
C24 C19 N2 117.9(4) . . ?
C19 C20 C21 118.9(4) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C22 C21 C20 119.2(4) . . ?
C22 C21 C25 121.7(3) . . ?
C20 C21 C25 119.1(4) . . ?
C21 C22 C23 120.8(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C24 119.9(4) . . ?
C22 C23 C26 120.9(3) . . ?
C24 C23 C26 119.1(3) . . ?
C19 C24 C23 117.9(4) . . ?
C19 C24 H24 121.1 . . ?
C23 C24 H24 121.1 . . ?
O6 C25 O5 124.1(4) . . ?
O6 C25 C21 119.4(4) . . ?
O5 C25 C21 116.6(4) . . ?
O7 C26 O8 126.5(4) . . ?
O7 C26 C23 118.1(3) . . ?
O8 C26 C23 115.4(3) . . ?
C5 N1 C1 121.5(3) . . ?
C5 N1 C11 119.4(3) . . ?
C1 N1 C11 119.1(3) . . ?
C8 N2 C10 119.8(4) . . ?
C8 N2 C19 121.9(4) . . ?
C10 N2 C19 118.4(4) . . ?
C17 O1 Mn1 134.5(3) . . ?
C18 O4 Mn1 127.3(2) . 3_667 ?
C18 O4 Mn1 124.0(2) . 1_565 ?
Mn1 O4 Mn1 105.67(11) 3_667 1_565 ?
C26 O8 Mn1 132.1(2) . 1_665 ?
Mn1 O9 H9A 102.6 . . ?
Mn1 O9 H9B 122.3 . . ?
H9A O9 H9B 93.5 . . ?
Mn1 O10 H10A 113.4 . . ?
Mn1 O10 H10B 108.4 . . ?
H10A O10 H10B 106.4 . . ?
O8 Mn1 O1 107.65(11) 1_445 . ?
O8 Mn1 O9 84.46(11) 1_445 . ?
O1 Mn1 O9 87.07(11) . . ?
O8 Mn1 O4 160.13(11) 1_445 3_667 ?
O1 Mn1 O4 91.32(11) . 3_667 ?
O9 Mn1 O4 90.80(11) . 3_667 ?
O8 Mn1 O4 88.15(11) 1_445 1_545 ?
O1 Mn1 O4 161.50(11) . 1_545 ?
O9 Mn1 O4 104.40(11) . 1_545 ?
O4 Mn1 O4 74.33(11) 3_667 1_545 ?
O8 Mn1 O10 89.00(11) 1_445 . ?
O1 Mn1 O10 81.44(12) . . ?
O9 Mn1 O10 164.41(12) . . ?
O4 Mn1 O10 99.92(11) 3_667 . ?
O4 Mn1 O10 89.47(11) 1_545 . ?

# start Validation Reply Form
_vrf_PLAT430_I                   
;
PROBLEM: Short Inter D...A Contact  O12    ..  O14     ..       2.32 Ang.  
RESPONSE: The 3 atoms O12, O14 and O15 have a half occupancy rate and are 
present one at a time in the structure.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 'Hydrothermal method'
