# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1881370'
loop_
_audit_author_name
_audit_author_address
'Teng Li'
;University of St andrews
United Kingdom
;
_audit_update_record             
;
2018-11-26 deposited with the CCDC.	2019-02-26 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         ?
_chemical_formula_sum            'C2 H10 F4 Mn N2'
_chemical_formula_weight         193.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Mn Mn 0.3368 0.7283 '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'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.1735(18)
_cell_length_b                   5.9868(13)
_cell_length_c                   5.9637(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.287(6)
_cell_angle_gamma                90
_cell_volume                     291.82(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    969
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.4

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.197
_exptl_crystal_F_000             194
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    2.258
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS-2008/1-G.M.Sheldrick
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device       
;
AFC8: Eulerian 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Pilatus 200K
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            3454
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.492
_diffrn_reflns_theta_max         25.265
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             526
_reflns_number_gt                517
_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_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0268P)²+0.0251P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.075(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         526
_refine_ls_number_parameters     44
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0142
_refine_ls_R_factor_gt           0.0141
_refine_ls_wR_factor_ref         0.0410
_refine_ls_wR_factor_gt          0.0409
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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 0.500000 0.500000 0.500000 0.00481(15) Uani 1 2 d S . P . .
F1 F 0.52763(7) 0.78515(10) 0.71488(10) 0.00837(19) Uani 1 1 d . . . . .
F2 F 0.75458(8) 0.45781(12) 0.53033(12) 0.00867(19) Uani 1 1 d . . . . .
N1 N 0.77052(15) 0.01272(14) 0.4885(2) 0.0081(3) Uani 1 1 d . . . . .
H1A H 0.693708 -0.059876 0.564687 0.012 Uiso 1 1 calc R U . . .
H1B H 0.760405 0.158859 0.512055 0.012 Uiso 1 1 calc R U . . .
H1C H 0.759087 -0.015855 0.342855 0.012 Uiso 1 1 calc R U . . .
C1 C 0.93402(12) -0.0620(2) 0.56508(17) 0.0071(2) Uani 1 1 d . . . . .
H1D H 0.945147 -0.221580 0.541215 0.009 Uiso 1 1 calc R U . . .
H1E H 0.946572 -0.032648 0.724186 0.009 Uiso 1 1 calc R U . . .

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 0.0052(2) 0.0047(2) 0.0045(2) -0.00003(6) -0.00028(12) 0.00000(6)
F1 0.0102(3) 0.0073(3) 0.0076(3) -0.0021(2) 0.0001(2) -0.0005(2)
F2 0.0071(4) 0.0092(3) 0.0097(4) 0.0001(3) 0.0000(3) 0.0003(3)
N1 0.0066(6) 0.0085(6) 0.0090(7) -0.0001(3) 0.0000(5) -0.0003(3)
C1 0.0064(5) 0.0076(5) 0.0074(5) 0.0009(5) -0.0009(4) -0.0002(5)

_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 F2 2.1030(8) 3_666 ?
Mn1 F2 2.1030(8) . ?
Mn1 F1 2.1449(6) 4_575 ?
Mn1 F1 2.1449(6) 2_646 ?
Mn1 F1 2.1458(6) 3_666 ?
Mn1 F1 2.1458(6) . ?
N1 C1 1.4793(17) . ?
C1 C1 1.525(2) 3_756 ?

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
F2 Mn1 F2 180.0 3_666 . ?
F2 Mn1 F1 88.16(3) 3_666 4_575 ?
F2 Mn1 F1 91.84(3) . 4_575 ?
F2 Mn1 F1 91.84(2) 3_666 2_646 ?
F2 Mn1 F1 88.16(2) . 2_646 ?
F1 Mn1 F1 180.0 4_575 2_646 ?
F2 Mn1 F1 86.73(2) 3_666 3_666 ?
F2 Mn1 F1 93.27(2) . 3_666 ?
F1 Mn1 F1 90.851(18) 4_575 3_666 ?
F1 Mn1 F1 89.149(19) 2_646 3_666 ?
F2 Mn1 F1 93.26(3) 3_666 . ?
F2 Mn1 F1 86.74(2) . . ?
F1 Mn1 F1 89.149(18) 4_575 . ?
F1 Mn1 F1 90.851(18) 2_646 . ?
F1 Mn1 F1 180.0 3_666 . ?
Mn1 F1 Mn1 159.94(4) 2_656 . ?
N1 C1 C1 109.61(11) . 3_756 ?

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
N1 H1A F1 0.89 1.88 2.7652(14) 177.8 1_545
N1 H1B F2 0.89 1.79 2.6795(13) 173.2 .
N1 H1C F2 0.89 1.90 2.7408(16) 157.8 4_565

_refine_diff_density_max         0.347
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.066

_shelx_res_file                  
;
TITL shelxt_a.res in P2(1)/c
    shelx.res
    created by SHELXL-2016/6 at 11:07:36 on 15-Nov-2018
CELL  0.71075   8.1735   5.9868   5.9637   90.000   90.287   90.000
ZERR     2.00   0.0018   0.0013   0.0014    0.000    0.006    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  MN F C N H
UNIT   2 8 4 4 20
EQIV $6 x, y-1, z
HTAB N1 F1_$6
HTAB N1 F2
EQIV $7 x, -y+1/2, z-1/2
HTAB N1 F2_$7
OMIT 6 2 3
MERG   2
FMAP   2
PLAN   5
ACTA
HTAB
BOND
LIST   6
L.S.  10
WGHT    0.026800    0.025100
EXTI    0.075083
FVAR       1.17957
MN1   1    0.500000    0.500000    0.500000    10.50000    0.00525    0.00469 =
         0.00450   -0.00003   -0.00028    0.00000
F1    2    0.527630    0.785151    0.714881    11.00000    0.01023    0.00730 =
         0.00760   -0.00210    0.00015   -0.00052
F2    2    0.754580    0.457807    0.530334    11.00000    0.00709    0.00922 =
         0.00969    0.00008    0.00002    0.00035
N1    4    0.770522    0.012717    0.488547    11.00000    0.00664    0.00848 =
         0.00903   -0.00013   -0.00003   -0.00026
AFIX  33
H1A   5    0.693708   -0.059876    0.564687    11.00000   -1.50000
H1B   5    0.760405    0.158859    0.512055    11.00000   -1.50000
H1C   5    0.759087   -0.015855    0.342855    11.00000   -1.50000
AFIX   0
C1    3    0.934019   -0.062043    0.565076    11.00000    0.00639    0.00765 =
         0.00740    0.00089   -0.00093   -0.00016
AFIX  23
H1D   5    0.945147   -0.221580    0.541215    11.00000   -1.20000
H1E   5    0.946572   -0.032648    0.724186    11.00000   -1.20000
AFIX   0
HKLF    4




REM  shelxt_a.res in P2(1)/c
REM R1 =  0.0141 for     517 Fo > 4sig(Fo)  and  0.0142 for all     526 data
REM     44 parameters refined using      0 restraints

END

WGHT      0.0262      0.0235

REM Instructions for potential hydrogen bonds
HTAB N1 F1_$6
HTAB N1 F2
HTAB N1 F1_$7
HTAB N1 F2_$7
HTAB C1 F2_$6
EQIV $8 x, -y+1/2, z+1/2
HTAB C1 F2_$8

REM Highest difference peak  0.347,  deepest hole -0.250,  1-sigma level  0.066
Q1    1   1.0000  0.0000  0.5000  10.50000  0.05    0.35
Q2    1   0.4780  0.8234  0.7820  11.00000  0.05    0.19
Q3    1   0.5245  0.6727  0.7276  11.00000  0.05    0.19
Q4    1   0.5148  0.8392  0.7162  11.00000  0.05    0.18
Q5    1   0.5615  0.8391  0.8259  11.00000  0.05    0.18
;
_shelx_res_checksum              27407
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1881390'
loop_
_audit_author_name
_audit_author_address
'Teng Li'
;University of St andrews
United Kingdom
;
_audit_update_record             
;
2018-11-26 deposited with the CCDC.	2019-02-26 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         ?
_chemical_formula_sum            'C2 H10 F4 Mn N2'
_chemical_formula_weight         193.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Mn Mn 0.3368 0.7283 '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'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.1634(7)
_cell_length_b                   5.9917(5)
_cell_length_c                   5.9622(5)
_cell_angle_alpha                90
_cell_angle_beta                 89.937(11)
_cell_angle_gamma                90
_cell_volume                     291.63(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    973
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      Loop
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.199
_exptl_crystal_F_000             194
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.259
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.580
_exptl_absorpt_process_details   SADABS-2008/1-G.M.Sheldrick
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  
;
SCXMini: Fixed Chi 2 circle
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            653
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.219
_diffrn_reflns_theta_max         27.545
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             653
_reflns_number_gt                631
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0249P)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         653
_refine_ls_number_parameters     44
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0202
_refine_ls_wR_factor_ref         0.0473
_refine_ls_wR_factor_gt          0.0470
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_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_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 0.500000 0.500000 0.500000 0.00802(12) Uani 1 2 d S . P . .
F1 F 0.75430(13) 0.54241(16) 0.4696(2) 0.0138(3) Uani 1 1 d . . . . .
F2 F 0.52788(12) 0.28464(15) 0.78429(17) 0.0134(2) Uani 1 1 d . . . . .
N1 N 0.76994(18) 0.9877(2) 0.5113(5) 0.0124(3) Uani 1 1 d . . . . .
H1C H 0.693087 1.060512 0.434901 0.019 Uiso 1 1 calc R U . . .
H1D H 0.759455 0.841721 0.487889 0.019 Uiso 1 1 calc R U . . .
H1E H 0.758739 1.016409 0.657008 0.019 Uiso 1 1 calc R U . . .
C1 C 0.9349(2) 1.0622(3) 0.4346(3) 0.0116(3) Uani 1 1 d . . . . .
H1A H 0.946670 1.221572 0.458557 0.014 Uiso 1 1 calc R U . . .
H1B H 0.947444 1.032602 0.275611 0.014 Uiso 1 1 calc R U . . .

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 0.00699(18) 0.00679(17) 0.0103(2) 0.00010(11) 0.0000(4) -0.00015(11)
F1 0.0080(4) 0.0147(4) 0.0187(7) 0.0004(5) 0.0005(5) -0.0001(4)
F2 0.0148(4) 0.0107(4) 0.0147(4) 0.0039(4) -0.0005(4) -0.0008(4)
N1 0.0083(6) 0.0131(6) 0.0158(8) -0.0003(5) -0.0006(13) -0.0001(5)
C1 0.0101(8) 0.0115(7) 0.0130(8) 0.0014(6) 0.0007(7) -0.0005(7)

_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 F1 2.0991(11) . ?
Mn1 F1 2.0991(11) 3_666 ?
Mn1 F2 2.1426(9) . ?
Mn1 F2 2.1426(9) 3_666 ?
Mn1 F2 2.1480(9) 4_565 ?
Mn1 F2 2.1480(9) 2_656 ?
N1 C1 1.490(2) . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
N1 H1E 0.8900 . ?
C1 C1 1.515(3) 3_776 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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
F1 Mn1 F1 180.00(5) . 3_666 ?
F1 Mn1 F2 92.03(4) . . ?
F1 Mn1 F2 87.97(4) 3_666 . ?
F1 Mn1 F2 87.97(4) . 3_666 ?
F1 Mn1 F2 92.03(4) 3_666 3_666 ?
F2 Mn1 F2 180.0 . 3_666 ?
F1 Mn1 F2 86.57(4) . 4_565 ?
F1 Mn1 F2 93.43(4) 3_666 4_565 ?
F2 Mn1 F2 89.096(11) . 4_565 ?
F2 Mn1 F2 90.904(10) 3_666 4_565 ?
F1 Mn1 F2 93.43(4) . 2_656 ?
F1 Mn1 F2 86.57(4) 3_666 2_656 ?
F2 Mn1 F2 90.904(11) . 2_656 ?
F2 Mn1 F2 89.095(10) 3_666 2_656 ?
F2 Mn1 F2 180.0 4_565 2_656 ?
Mn1 F2 Mn1 160.15(5) . 2_646 ?
C1 N1 H1C 109.5 . . ?
C1 N1 H1D 109.5 . . ?
H1C N1 H1D 109.5 . . ?
C1 N1 H1E 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
N1 C1 C1 109.20(19) . 3_776 ?
N1 C1 H1A 109.8 . . ?
C1 C1 H1A 109.8 3_776 . ?
N1 C1 H1B 109.8 . . ?
C1 C1 H1B 109.8 3_776 . ?
H1A C1 H1B 108.3 . . ?

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
N1 H1C F2 0.89 1.87 2.757(2) 177.9 4_575
N1 H1D F1 0.89 1.80 2.6828(16) 173.0 .
N1 H1E F1 0.89 1.90 2.741(4) 157.6 4_576

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.066

_shelx_res_file                  
;
TITL shelxt_a.res in P2(1)/c
    shelx.res
    created by SHELXL-2016/6 at 15:44:32 on 15-Nov-2018
REM Old TITL  TENG92

REM SHELXT solution in P2(1)/c
REM R1 0.160,  Rweak 0.032,  Alpha 0.095,  Orientation a'=c, b'=-b, c'=a
REM Formula found by SHELXT:  Mn F2 C2 N2 O2

CELL  0.71075   8.1634   5.9917   5.9622   90.000   89.937   90.000
ZERR    2.000   0.0007   0.0005   0.0005    0.000    0.011    0.000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC MN F C N H
UNIT 2  8 4 4 20
L.S. 10
ACTA
BOND $H
HTAB
EQIV $6 x, -y+3/2, z-1/2
HTAB N1 F2_$6
HTAB N1 F1
EQIV $7 x, -y+3/2, z+1/2
HTAB N1 F1_$7
LIST 4
FMAP 2
PLAN 5
WGHT    0.024900
BASF   0.40066
FVAR      31.11592
MN1   1    0.500000    0.500000    0.500000    10.50000    0.00699    0.00679 =
         0.01029    0.00010    0.00004   -0.00015
F1    2    0.754300    0.542411    0.469561    11.00000    0.00804    0.01472 =
         0.01871    0.00036    0.00051   -0.00006
F2    2    0.527876    0.284641    0.784289    11.00000    0.01482    0.01071 =
         0.01467    0.00392   -0.00049   -0.00083
N1    4    0.769935    0.987717    0.511333    11.00000    0.00830    0.01312 =
         0.01584   -0.00027   -0.00057   -0.00010
AFIX  33
H1C   5    0.693087    1.060512    0.434901    11.00000   -1.50000
H1D   5    0.759455    0.841721    0.487889    11.00000   -1.50000
H1E   5    0.758739    1.016409    0.657008    11.00000   -1.50000
AFIX   0
C1    3    0.934909    1.062246    0.434647    11.00000    0.01008    0.01155 =
         0.01305    0.00139    0.00071   -0.00048
AFIX  23
H1A   5    0.946670    1.221572    0.458557    11.00000   -1.20000
H1B   5    0.947444    1.032602    0.275611    11.00000   -1.20000

AFIX   0
HKLF 5




REM  shelxt_a.res in P2(1)/c
REM R1 =  0.0202 for     631 Fo > 4sig(Fo)  and  0.0209 for all     653 data
REM     44 parameters refined using      0 restraints

END

WGHT      0.0235      0.0000

REM Instructions for potential hydrogen bonds
HTAB N1 F2_$6
HTAB N1 F1
HTAB N1 F1_$7
EQIV $8 x, y+1, z
HTAB N1 F2_$8
HTAB C1 F1_$8
HTAB C1 F1_$6

REM Highest difference peak  0.427,  deepest hole -0.377,  1-sigma level  0.066
Q1    1   1.0000  1.0000  0.5000  10.50000  0.05    0.43
Q2    1   0.6666  0.5018  0.4256  11.00000  0.05    0.30
Q3    1   0.4747  0.1463  0.8536  11.00000  0.05    0.26
Q4    1   0.4908  0.3488  0.6462  11.00000  0.05    0.23
Q5    1   0.4165  0.4109  0.4784  11.00000  0.05    0.22
;
_shelx_res_checksum              71363
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1881392'
loop_
_audit_author_name
_audit_author_address
'Teng Li'
;University of St andrews
United Kingdom
;
_audit_update_record             
;
2018-11-26 deposited with the CCDC.	2019-02-26 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         ?
_chemical_formula_sum            'C2 H10 F4 Mn N2'
_chemical_formula_weight         193.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Mn Mn 0.3368 0.7283 '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'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.1632(7)
_cell_length_b                   6.0028(5)
_cell_length_c                   5.9759(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.183(13)
_cell_angle_gamma                90
_cell_volume                     292.83(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    926
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Chip
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.190
_exptl_crystal_F_000             194
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    2.250
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS-2008/1-G.M.Sheldrick
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  
;
SCXMini: Fixed Chi 2 circle
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            666
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.214
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             666
_reflns_number_gt                586
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)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         666
_refine_ls_number_parameters     44
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.500000 1.000000 0.500000 0.0127(2) Uani 1 2 d S . P . .
F1 F 0.5286(2) 0.7169(3) 0.7173(4) 0.0213(4) Uani 1 1 d . . . . .
F2 F 0.2455(2) 0.9573(3) 0.4691(4) 0.0205(5) Uani 1 1 d . . . . .
N1 N 0.2299(3) 0.5121(4) 0.5103(10) 0.0186(6) Uani 1 1 d . . . . .
H1C H 0.306592 0.440048 0.433364 0.028 Uiso 1 1 calc R U . . .
H1D H 0.240228 0.657992 0.487864 0.028 Uiso 1 1 calc R U . . .
H1E H 0.241583 0.482525 0.655435 0.028 Uiso 1 1 calc R U . . .
C1 C 0.0652(4) 0.4382(5) 0.4340(6) 0.0190(7) Uani 1 1 d . . . . .
H1A H 0.053660 0.278985 0.456815 0.023 Uiso 1 1 calc R U . . .
H1B H 0.052194 0.468794 0.275548 0.023 Uiso 1 1 calc R U . . .

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 0.0098(3) 0.0105(3) 0.0177(4) -0.0002(2) -0.0027(7) -0.0001(2)
F1 0.0212(8) 0.0167(8) 0.0261(9) 0.0064(7) 0.0005(9) 0.0008(7)
F2 0.0116(8) 0.0231(8) 0.0269(13) -0.0013(9) -0.0001(10) -0.0006(6)
N1 0.0130(12) 0.0196(11) 0.0231(16) -0.0002(10) 0.000(2) 0.0000(9)
C1 0.0143(15) 0.0160(13) 0.0267(19) -0.0027(13) -0.0023(15) -0.0002(13)

_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 F2 2.100(2) 3_676 ?
Mn1 F2 2.101(2) . ?
Mn1 F1 2.1462(18) 4_575 ?
Mn1 F1 2.1462(18) 2_656 ?
Mn1 F1 2.1510(17) . ?
Mn1 F1 2.1510(17) 3_676 ?
N1 C1 1.486(4) . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
N1 H1E 0.8900 . ?
C1 C1 1.521(7) 3_566 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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
F2 Mn1 F2 180.0 3_676 . ?
F2 Mn1 F1 91.92(8) 3_676 4_575 ?
F2 Mn1 F1 88.08(7) . 4_575 ?
F2 Mn1 F1 88.08(7) 3_676 2_656 ?
F2 Mn1 F1 91.92(7) . 2_656 ?
F1 Mn1 F1 180.00(7) 4_575 2_656 ?
F2 Mn1 F1 86.45(8) 3_676 . ?
F2 Mn1 F1 93.55(8) . . ?
F1 Mn1 F1 89.088(17) 4_575 . ?
F1 Mn1 F1 90.912(17) 2_656 . ?
F2 Mn1 F1 93.55(8) 3_676 3_676 ?
F2 Mn1 F1 86.45(8) . 3_676 ?
F1 Mn1 F1 90.912(17) 4_575 3_676 ?
F1 Mn1 F1 89.088(17) 2_656 3_676 ?
F1 Mn1 F1 180.0 . 3_676 ?
Mn1 F1 Mn1 160.50(11) 2_646 . ?
C1 N1 H1C 109.5 . . ?
C1 N1 H1D 109.5 . . ?
H1C N1 H1D 109.5 . . ?
C1 N1 H1E 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
N1 C1 C1 109.2(4) . 3_566 ?
N1 C1 H1A 109.8 . . ?
C1 C1 H1A 109.8 3_566 . ?
N1 C1 H1B 109.8 . . ?
C1 C1 H1B 109.8 3_566 . ?
H1A C1 H1B 108.3 . . ?

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
N1 H1C F1 0.89 1.88 2.765(4) 177.6 3_666
N1 H1D F2 0.89 1.80 2.687(3) 173.5 .
N1 H1E F2 0.89 1.91 2.750(7) 157.0 4_576

_refine_diff_density_max         0.722
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.112

_shelx_res_file                  
;
TITL shelxt_a.res in P2(1)/c
    shelx.res
    created by SHELXL-2016/6 at 15:49:40 on 15-Nov-2018
CELL  0.71075   8.1632   6.0028   5.9759   90.000   90.183   90.000
ZERR     2.00   0.0007   0.0005   0.0005    0.000    0.013    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  MN  F  C  N  H
UNIT   2  8  4  4  20
MERG   2
FMAP   2
PLAN   5
ACTA
BOND   $H
HTAB
EQIV $6 -x+1, -y+1, -z+1
HTAB N1 F1_$6
HTAB N1 F2
EQIV $7 x, -y+3/2, z+1/2
HTAB N1 F2_$7
LIST   4
L.S.  20
WGHT    0.047600
BASF   0.39745
FVAR      32.13431
MN1   1    0.500000    1.000000    0.500000    10.50000    0.00979    0.01048 =
         0.01774   -0.00015   -0.00269   -0.00005
F1    2    0.528552    0.716873    0.717275    11.00000    0.02117    0.01673 =
         0.02615    0.00644    0.00049    0.00079
F2    2    0.245541    0.957314    0.469070    11.00000    0.01159    0.02310 =
         0.02689   -0.00131   -0.00007   -0.00061
N1    4    0.229923    0.512101    0.510318    11.00000    0.01299    0.01962 =
         0.02307   -0.00024   -0.00046   -0.00001
AFIX  33
H1C   5    0.306592    0.440048    0.433364    11.00000   -1.50000
H1D   5    0.240228    0.657992    0.487864    11.00000   -1.50000
H1E   5    0.241583    0.482525    0.655435    11.00000   -1.50000
AFIX   0
C1    3    0.065218    0.438190    0.433990    11.00000    0.01427    0.01603 =
         0.02665   -0.00273   -0.00227   -0.00025
AFIX  23
H1A   5    0.053660    0.278985    0.456815    11.00000   -1.20000
H1B   5    0.052194    0.468794    0.275548    11.00000   -1.20000

AFIX   0
HKLF    5




REM  shelxt_a.res in P2(1)/c
REM R1 =  0.0338 for     586 Fo > 4sig(Fo)  and  0.0373 for all     666 data
REM     44 parameters refined using      0 restraints

END

WGHT      0.0442      0.0000

REM Instructions for potential hydrogen bonds
HTAB N1 F1_$6
HTAB N1 F2
EQIV $1 -x+1, y-1/2, -z+3/2
HTAB N1 F1_$1
HTAB N1 F2_$7
EQIV $8 x, y-1, z
HTAB C1 F2_$8
EQIV $4 x, -y+3/2, z-1/2
HTAB C1 F2_$4

REM Highest difference peak  0.722,  deepest hole -0.591,  1-sigma level  0.112
Q1    1   0.4550  1.0003  0.3660  11.00000  0.05    0.72
Q2    1   0.4788  0.7113  0.5873  11.00000  0.05    0.44
Q3    1   0.2352  1.0213  0.6390  11.00000  0.05    0.40
Q4    1   0.5332  0.8684  0.4134  11.00000  0.05    0.39
Q5    1   0.5460  0.7823  0.9032  11.00000  0.05    0.37
;
_shelx_res_checksum              46499
