# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1486500'
_audit_update_record             
;
2016-06-20 deposited with the CCDC.
2016-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H24 F12 Mn N2 O10'
_chemical_formula_sum            'C16 H24 F12 Mn N2 O10'
_chemical_formula_weight         687.31

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'
F F 0.0171 0.0103 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   9.0076(6)
_cell_length_b                   16.6072(12)
_cell_length_c                   18.0267(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2696.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    114(2)
_cell_measurement_reflns_used    5506
_cell_measurement_theta_min      3.4920
_cell_measurement_theta_max      30.3830

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_F_000             1388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.623
_shelx_estimated_absorpt_T_min   0.746
_shelx_estimated_absorpt_T_max   0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3934
_exptl_absorpt_correction_T_max  0.4329
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      114(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 5.2020
_diffrn_reflns_number            13593
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.197
_diffrn_reflns_theta_max         28.694
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3427
_reflns_number_gt                2954
_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_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0567P)²+1.8958P] 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         3427
_refine_ls_number_parameters     207
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1153
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.174
_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 0.5000 0.5000 0.5000 0.01687(13) Uani 1 2 d S . P . .
F1 F 0.97451(15) 0.61858(8) 0.39865(8) 0.0318(3) Uani 1 1 d . . . . .
F2 F 0.84871(17) 0.55782(10) 0.31508(7) 0.0432(4) Uani 1 1 d . . . . .
F3 F 1.03999(18) 0.50062(8) 0.36325(10) 0.0412(4) Uani 1 1 d . . . . .
F4 F 0.3516(7) 0.3925(2) 0.27195(18) 0.0486(10) Uani 0.743(11) 1 d D . P A 1
F5 F 0.5654(3) 0.3348(4) 0.27532(18) 0.0516(10) Uani 0.743(11) 1 d D U P A 1
F6 F 0.3641(6) 0.2684(3) 0.2974(3) 0.0411(10) Uani 0.743(11) 1 d D . P A 1
F4' F 0.4114(15) 0.3938(6) 0.2646(6) 0.0486(10) Uani 0.257(11) 1 d D . P A 2
F5' F 0.5654(10) 0.2998(8) 0.2872(5) 0.0516(10) Uani 0.257(11) 1 d D . P A 2
F6' F 0.3390(18) 0.2776(9) 0.2993(10) 0.0411(10) Uani 0.257(11) 1 d D . P A 2
O1 O 0.70582(15) 0.55044(8) 0.45106(8) 0.0221(3) Uani 1 1 d . . . . .
O2 O 0.86069(16) 0.44544(9) 0.46583(9) 0.0270(3) Uani 1 1 d . . . . .
O3 O 0.47895(17) 0.43307(9) 0.40130(8) 0.0261(3) Uani 1 1 d . . . . .
O4 O 0.43986(17) 0.30431(9) 0.43610(8) 0.0239(3) Uani 1 1 d . . . . .
O5 O 0.63974(16) 0.40534(8) 0.54919(8) 0.0209(3) Uani 1 1 d . . . . .
H5 H 0.733(4) 0.4178(18) 0.5282(18) 0.049(8) Uiso 1 1 d . . . . .
N1 N 0.46652(18) 0.27593(10) 0.58626(9) 0.0182(3) Uani 1 1 d . . . . .
H1 H 0.468(3) 0.2996(14) 0.5434(14) 0.018(6) Uiso 1 1 d . . . . .
C1 C 0.8199(2) 0.50968(11) 0.43832(11) 0.0201(4) Uani 1 1 d . . . . .
C2 C 0.9224(2) 0.54606(13) 0.37834(11) 0.0248(4) Uani 1 1 d . . . . .
C3 C 0.4515(2) 0.35993(12) 0.39157(10) 0.0191(4) Uani 1 1 d D . . . .
C4 C 0.4350(2) 0.33768(13) 0.30904(11) 0.0246(4) Uani 1 1 d D . . . .
C5 C 0.6530(2) 0.37867(13) 0.62410(11) 0.0239(4) Uani 1 1 d . . . . .
H5A H 0.6698 0.4251 0.6575 0.029 Uiso 1 1 calc R U . . .
H5B H 0.7378 0.3411 0.6291 0.029 Uiso 1 1 calc R U . . .
C6 C 0.5091(2) 0.33650(13) 0.64399(11) 0.0216(4) Uani 1 1 d . . . . .
H6A H 0.5206 0.3091 0.6924 0.026 Uiso 1 1 calc R U . . .
H6B H 0.4290 0.3769 0.6489 0.026 Uiso 1 1 calc R U . . .
C7 C 0.3133(2) 0.24498(13) 0.59957(12) 0.0242(4) Uani 1 1 d . . . . .
H7A H 0.2870 0.2064 0.5606 0.036 Uiso 1 1 calc R U . . .
H7B H 0.2429 0.2900 0.5989 0.036 Uiso 1 1 calc R U . . .
H7C H 0.3093 0.2182 0.6480 0.036 Uiso 1 1 calc R U . . .
C8 C 0.5735(2) 0.20778(12) 0.58032(12) 0.0248(4) Uani 1 1 d . . . . .
H8A H 0.5782 0.1792 0.6278 0.037 Uiso 1 1 calc R U . . .
H8B H 0.6721 0.2287 0.5678 0.037 Uiso 1 1 calc R U . . .
H8C H 0.5405 0.1706 0.5414 0.037 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 O3 2.1065(15) 5_666 ?
Mn1 O3 2.1065(15) . Y
Mn1 O5 2.2005(14) . Y
Mn1 O5 2.2005(14) 5_666 ?
Mn1 O1 2.2175(14) 5_666 ?
Mn1 O1 2.2175(14) . Y
F1 C2 1.343(2) . ?
F2 C2 1.334(3) . ?
F3 C2 1.329(2) . ?
F4 C4 1.356(4) . ?
F5 C4 1.324(3) . ?
F6 C4 1.332(4) . ?
F4' C4 1.247(8) . ?
F5' C4 1.390(8) . ?
F6' C4 1.332(9) . ?
O1 C1 1.252(2) . ?
O2 C1 1.232(2) . ?
O3 C3 1.252(2) . ?
O4 C3 1.228(2) . ?
O5 C5 1.426(2) . ?
O5 H5 0.94(3) . ?
N1 C8 1.490(3) . ?
N1 C7 1.492(2) . ?
N1 C6 1.497(3) . ?
N1 H1 0.87(2) . ?
C1 C2 1.545(3) . ?
C3 C4 1.540(3) . ?
C5 C6 1.517(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
O3 Mn1 O3 180.0 5_666 . Y
O3 Mn1 O5 89.15(6) 5_666 . Y
O3 Mn1 O5 90.85(6) . . Y
O3 Mn1 O5 90.85(6) 5_666 5_666 Y
O3 Mn1 O5 89.15(6) . 5_666 Y
O5 Mn1 O5 180.0 . 5_666 Y
O3 Mn1 O1 86.48(6) 5_666 5_666 Y
O3 Mn1 O1 93.52(6) . 5_666 Y
O5 Mn1 O1 92.75(5) . 5_666 Y
O5 Mn1 O1 87.25(5) 5_666 5_666 Y
O3 Mn1 O1 93.52(6) 5_666 . Y
O3 Mn1 O1 86.48(6) . . Y
O5 Mn1 O1 87.25(5) . . Y
O5 Mn1 O1 92.75(5) 5_666 . Y
O1 Mn1 O1 180.0 5_666 . Y
C1 O1 Mn1 123.72(12) . . ?
C3 O3 Mn1 130.40(13) . . ?
C5 O5 Mn1 130.65(13) . . ?
C5 O5 H5 112.0(19) . . ?
Mn1 O5 H5 101.0(19) . . ?
C8 N1 C7 110.36(15) . . ?
C8 N1 C6 113.24(16) . . ?
C7 N1 C6 110.88(16) . . ?
C8 N1 H1 105.9(15) . . ?
C7 N1 H1 108.1(16) . . ?
C6 N1 H1 108.1(15) . . ?
O2 C1 O1 129.70(19) . . ?
O2 C1 C2 116.25(18) . . ?
O1 C1 C2 114.05(17) . . ?
F3 C2 F2 107.76(18) . . ?
F3 C2 F1 106.65(17) . . ?
F2 C2 F1 106.00(17) . . ?
F3 C2 C1 113.42(17) . . ?
F2 C2 C1 110.99(17) . . ?
F1 C2 C1 111.62(16) . . ?
O4 C3 O3 130.91(18) . . ?
O4 C3 C4 116.28(17) . . ?
O3 C3 C4 112.78(17) . . ?
F5 C4 F6 108.7(3) . . ?
F4' C4 F6' 111.4(9) . . ?
F5 C4 F4 106.8(2) . . ?
F6 C4 F4 103.7(3) . . ?
F4' C4 F5' 107.5(6) . . ?
F6' C4 F5' 99.9(8) . . ?
F4' C4 C3 117.3(6) . . ?
F5 C4 C3 111.5(2) . . ?
F6 C4 C3 114.0(3) . . ?
F6' C4 C3 111.7(8) . . ?
F4 C4 C3 111.6(2) . . ?
F5' C4 C3 107.5(4) . . ?
O5 C5 C6 107.19(15) . . ?
O5 C5 H5A 110.3 . . ?
C6 C5 H5A 110.3 . . ?
O5 C5 H5B 110.3 . . ?
C6 C5 H5B 110.3 . . ?
H5A C5 H5B 108.5 . . ?
N1 C6 C5 111.40(16) . . ?
N1 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8C O2 0.98 2.52 3.292(3) 135.5 4_456
C8 H8B O4 0.98 2.47 3.320(3) 144.3 4_556
C7 H7B F1 0.98 2.48 3.443(3) 167.9 5_666
C6 H6B O1 0.99 2.49 3.195(2) 128.3 5_666
C5 H5B F6 0.99 2.52 3.404(5) 148.2 4_556
N1 H1 O4 0.87(2) 1.95(2) 2.758(2) 154(2) .
O5 H5 O2 0.94(3) 1.67(3) 2.581(2) 160(3) .

_refine_diff_density_max         0.805
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.075

