# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 2172908'
loop_
_audit_author_name
_audit_author_address
'Zhenhong Wei'
;Nanchang University
China
;
_audit_update_record             
;
2022-05-16 deposited with the CCDC.	2022-09-26 downloaded from the CCDC.
;
_audit_creation_date             2022-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'Cl3 Mn, C3 H11 N2'
_chemical_formula_sum            'C3 H11 N2 Cl3 Mn'
_chemical_formula_weight         236.43
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   6.395(2)
_cell_length_b                   9.493(3)
_cell_length_c                   14.804(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     898.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3717
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.75
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.285
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0894 before and 0.0476 after correction.
The Ratio of minimum to maximum transmission is 0.6630.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_meas      1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bulk
_exptl_crystal_F_000             476.0
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5134
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.746
_diffrn_reflns_theta_min         2.549
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                984
_reflns_number_total             1119
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       0.025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     56
_refine_ls_number_reflns         1119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+1.7031P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1057
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H2B(0.5) H2A(0.5) H2C(0.5)
3.a Idealised Me refined as rotating group:
 C2(H2B,H2A,H2C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N -0.2771(6) -1.250000 0.3990(2) 0.0287(8) Uani 1 2 d S T P . .
N2 N -0.3313(9) -1.250000 0.3037(3) 0.0482(13) Uani 1 2 d S T P . .
C2 C -0.4728(10) -1.250000 0.4558(4) 0.0560(16) Uani 1 2 d S T P . .
H2B H -0.567866 -1.320078 0.433426 0.084 Uiso 0.5 1 calc GR . . A -1
H2A H -0.537851 -1.158974 0.452745 0.084 Uiso 0.5 1 calc GR . . A -1
H2C H -0.437441 -1.270948 0.517373 0.084 Uiso 0.5 1 calc GR . . A -1
C1 C -0.1571(7) -1.3787(5) 0.4178(3) 0.0544(11) Uani 1 1 d . . . . .
H1A H -0.239409 -1.459600 0.402106 0.082 Uiso 1 1 calc GR . . . .
H1B H -0.122459 -1.382211 0.480839 0.082 Uiso 1 1 calc GR . . . .
H1C H -0.030903 -1.378234 0.382640 0.082 Uiso 1 1 calc GR . . . .
Mn1 Mn -0.59100(9) -1.250000 0.75011(4) 0.0211(2) Uani 1 2 d S T P . .
Cl2 Cl -0.34268(14) -1.250000 0.88259(7) 0.0249(3) Uani 1 2 d S T P . .
Cl1 Cl -0.34087(10) -1.06770(8) 0.68158(5) 0.0268(2) Uani 1 1 d . . . . .
H2 H -0.397(8) -1.174(5) 0.297(3) 0.072(17) Uiso 1 1 d . . . . .

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
N1 0.041(2) 0.0224(18) 0.0228(17) 0.000 -0.0016(16) 0.000
N2 0.078(4) 0.044(3) 0.023(2) 0.000 -0.007(2) 0.000
C2 0.055(4) 0.064(4) 0.049(3) 0.000 0.015(3) 0.000
C1 0.069(3) 0.035(2) 0.059(3) -0.001(2) -0.011(2) 0.0210(19)
Mn1 0.0129(3) 0.0247(4) 0.0256(4) 0.000 -0.0006(2) 0.000
Cl2 0.0196(5) 0.0336(6) 0.0216(5) 0.000 -0.0004(3) 0.000
Cl1 0.0203(4) 0.0250(4) 0.0353(4) 0.0069(3) -0.0005(3) 0.0004(3)

_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
N1 N2 1.453(6) . ?
N1 C2 1.508(7) . ?
N1 C1 1.469(4) . ?
N1 C1 1.469(4) 8_535 ?
N2 H2 0.84(5) 8_535 ?
N2 H2 0.84(5) . ?
C2 H2B 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
Mn1 Mn1 3.1975(10) 6_657 ?
Mn1 Mn1 3.1975(10) 6_557 ?
Mn1 Cl2 2.5236(12) . ?
Mn1 Cl2 2.5396(12) 6_557 ?
Mn1 Cl1 2.5657(9) . ?
Mn1 Cl1 2.5634(9) 6_557 ?
Mn1 Cl1 2.5657(10) 8_535 ?
Mn1 Cl1 2.5634(9) 3_426 ?

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
N2 N1 C2 110.1(4) . . ?
N2 N1 C1 107.9(3) . 8_535 ?
N2 N1 C1 107.9(3) . . ?
C1 N1 C2 109.2(3) 8_535 . ?
C1 N1 C2 109.2(3) . . ?
C1 N1 C1 112.5(4) . 8_535 ?
N1 N2 H2 104(3) . 8_535 ?
N1 N2 H2 104(3) . . ?
H2 N2 H2 118(7) . 8_535 ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2B C2 H2A 109.5 . . ?
H2B C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Mn1 Mn1 Mn1 179.89(4) 6_657 6_557 ?
Cl2 Mn1 Mn1 50.62(3) 6_557 6_557 ?
Cl2 Mn1 Mn1 51.06(3) . 6_657 ?
Cl2 Mn1 Mn1 129.27(4) 6_557 6_657 ?
Cl2 Mn1 Mn1 129.05(4) . 6_557 ?
Cl2 Mn1 Cl2 179.67(4) . 6_557 ?
Cl2 Mn1 Cl1 84.84(3) 6_557 6_557 ?
Cl2 Mn1 Cl1 94.91(3) . 3_426 ?
Cl2 Mn1 Cl1 85.12(3) . . ?
Cl2 Mn1 Cl1 94.91(3) . 6_557 ?
Cl2 Mn1 Cl1 85.12(3) . 8_535 ?
Cl2 Mn1 Cl1 95.12(3) 6_557 8_535 ?
Cl2 Mn1 Cl1 84.84(3) 6_557 3_426 ?
Cl2 Mn1 Cl1 95.12(3) 6_557 . ?
Cl1 Mn1 Mn1 128.59(3) 3_426 6_657 ?
Cl1 Mn1 Mn1 51.47(2) 6_557 6_557 ?
Cl1 Mn1 Mn1 128.54(3) . 6_557 ?
Cl1 Mn1 Mn1 128.59(3) 6_557 6_657 ?
Cl1 Mn1 Mn1 128.54(3) 8_535 6_557 ?
Cl1 Mn1 Mn1 51.40(2) 8_535 6_657 ?
Cl1 Mn1 Mn1 51.47(2) 3_426 6_557 ?
Cl1 Mn1 Mn1 51.40(2) . 6_657 ?
Cl1 Mn1 Cl1 84.83(4) 8_535 . ?
Cl1 Mn1 Cl1 95.12(4) 6_557 . ?
Cl1 Mn1 Cl1 179.94(3) 3_426 . ?
Cl1 Mn1 Cl1 95.12(4) 3_426 8_535 ?
Cl1 Mn1 Cl1 179.94(3) 6_557 8_535 ?
Cl1 Mn1 Cl1 84.92(4) 3_426 6_557 ?
Mn1 Cl2 Mn1 78.32(4) . 6_657 ?
Mn1 Cl1 Mn1 77.13(3) 6_657 . ?

_shelx_res_file                  
;
TITL t P 1 21/c 1 R = 0.18 New:Pnma
    t.res
    created by SHELXL-2018/3 at 13:27:55 on 25-Apr-2022
CELL 0.71073 6.395 9.493 14.804 90 90 90
ZERR 2 0.002 0.003 0.004 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,0.5-Z
SYMM -X,0.5+Y,-Z
SFAC C Cl Mn N H
UNIT 16 12 4 4 8

L.S. 5
PLAN  -20
TEMP 23
BOND $H
CONF
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\t.hkl">
REM </olex2.extras>

WGHT    0.042400    1.703100
EXTI    0.025320
FVAR       0.21662
N1    4   -0.277070   -1.250000    0.399045    10.50000    0.04076    0.02243 =
         0.02282    0.00000   -0.00157    0.00000
N2    4   -0.331329   -1.250000    0.303722    10.50000    0.07784    0.04377 =
         0.02313    0.00000   -0.00721    0.00000
C2    1   -0.472837   -1.250000    0.455802    10.50000    0.05450    0.06418 =
         0.04930    0.00000    0.01458    0.00000
PART -1
AFIX 137
H2B   5   -0.567866   -1.320078    0.433426    10.50000   -1.50000
H2A   5   -0.537851   -1.158974    0.452745    10.50000   -1.50000
H2C   5   -0.437441   -1.270948    0.517373    10.50000   -1.50000
AFIX   0
PART 0
C1    1   -0.157068   -1.378653    0.417780    11.00000    0.06897    0.03504 =
         0.05908   -0.00136   -0.01078    0.02100
AFIX 137
H1A   5   -0.239409   -1.459600    0.402106    11.00000   -1.50000
H1B   5   -0.122459   -1.382211    0.480839    11.00000   -1.50000
H1C   5   -0.030903   -1.378234    0.382640    11.00000   -1.50000
AFIX   0

MN1   3   -0.590997   -1.250000    0.750105    10.50000    0.01294    0.02469 =
         0.02561    0.00000   -0.00060    0.00000
CL2   2   -0.342681   -1.250000    0.882590    10.50000    0.01962    0.03356 =
         0.02163    0.00000   -0.00042    0.00000
CL1   2   -0.340870   -1.067700    0.681579    11.00000    0.02028    0.02497 =
         0.03529    0.00693   -0.00052    0.00037
H2    5   -0.397228   -1.173915    0.296784    11.00000    0.07206
HKLF 4 1 0 -1 0 -0.3333 0 -0.3333 0.3333 0 -0.6667




REM  t P 1 21/c 1 R = 0.18 New:Pnma
REM wR2 = 0.1057, GooF = S = 1.120, Restrained GooF = 1.120 for all data
REM R1 = 0.0442 for 984 Fo > 4sig(Fo) and 0.0488 for all 1119 data
REM 56 parameters refined using 0 restraints

END

WGHT      0.0426      1.6933

REM Highest difference peak  0.807,  deepest hole -0.505,  1-sigma level  0.112
Q1    1  -0.0881 -0.8351  0.3326  11.00000  0.05    0.81
Q2    1  -0.5924 -0.8375  0.3329  11.00000  0.05    0.74
Q3    1   0.1480 -1.4780  0.3876  11.00000  0.05    0.66
Q4    1  -0.3436 -1.0039  0.2547  11.00000  0.05    0.65
Q5    1  -0.3452 -0.8302  0.2964  11.00000  0.05    0.60
Q6    1  -0.3477 -1.2500  0.5110  10.50000  0.05    0.59
Q7    1  -0.6645 -1.1425  0.5351  11.00000  0.05    0.56
Q8    1  -0.1457 -1.0972  0.3410  11.00000  0.05    0.54
Q9    1  -0.4083 -0.9164  0.4112  11.00000  0.05    0.49
Q10   1  -0.1625 -0.8914  0.2249  11.00000  0.05    0.47
Q11   1  -0.6576 -1.1082  0.4651  11.00000  0.05    0.44
Q12   1  -0.0907 -1.4212  0.5815  11.00000  0.05    0.43
Q13   1   0.1645 -1.4526  0.4543  11.00000  0.05    0.41
Q14   1  -0.0201 -1.1764  0.3731  11.00000  0.05    0.35
Q15   1  -0.3506 -1.2003  0.4230  11.00000  0.05    0.34
Q16   1   0.1599 -0.8296  0.4092  11.00000  0.05    0.33
Q17   1  -0.2485 -1.0875  0.2297  11.00000  0.05    0.31
Q18   1  -0.6844 -1.0032  0.3549  11.00000  0.05    0.31
Q19   1  -0.1454 -0.8036  0.4453  11.00000  0.05    0.30
Q20   1  -0.3570 -1.1742  0.4575  11.00000  0.05    0.27
;
_shelx_res_checksum              16108
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2172909'
loop_
_audit_author_name
_audit_author_address
'Zhenhong Wei'
;Nanchang University
China
;
_audit_update_record             
;
2022-05-16 deposited with the CCDC.	2022-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C5 H13 F N), Cl4 Mn'
_chemical_formula_sum            'C10 H26 Cl4 F2 Mn N2'
_chemical_formula_weight         409.07

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   9.3174(19)
_cell_length_b                   15.306(3)
_cell_length_c                   13.558(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.311(4)
_cell_angle_gamma                90.00
_cell_volume                     1925.234
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3351
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      23.73

_exptl_crystal_description       bulk
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      1.411
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             844.0
_exptl_absorpt_coefficient_mu    1.248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5437
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11425
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         27.75
_reflns_number_total             4446
_reflns_number_gt                3054
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)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_extinction_coef       ?
_refine_ls_number_reflns         4446
_refine_ls_number_parameters     178
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.2022
_refine_ls_wR_factor_gt          0.1794
_refine_ls_goodness_of_fit_ref   1.263
_refine_ls_restrained_S_all      1.300
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.27086(6) 0.59962(4) 0.23478(4) 0.0369(2) Uani 1 1 d . . .
F1 F 0.3012(9) 0.5215(4) 0.6557(4) 0.185(3) Uani 1 1 d . . .
F2 F 0.1145(4) 0.2480(3) 0.6486(3) 0.0925(11) Uani 1 1 d . . .
N1 N 0.2237(5) 0.5847(3) 0.8593(3) 0.0568(11) Uani 1 1 d U . .
N2 N 0.2730(4) 0.3179(2) 0.4714(2) 0.0403(8) Uani 1 1 d . . .
C1 C 0.2980(12) 0.6565(7) 0.9121(8) 0.192(6) Uani 1 1 d . . .
H1A H 0.3440 0.6357 0.9739 0.288 Uiso 1 1 calc R . .
H1B H 0.2297 0.7013 0.9245 0.288 Uiso 1 1 calc R . .
H1C H 0.3693 0.6801 0.8727 0.288 Uiso 1 1 calc R . .
C2 C 0.2982(10) 0.4987(5) 0.8701(6) 0.121(3) Uani 1 1 d . . .
H2A H 0.3193 0.4856 0.9392 0.182 Uiso 1 1 calc R . .
H2B H 0.3863 0.5010 0.8387 0.182 Uiso 1 1 calc R . .
H2C H 0.2369 0.4541 0.8395 0.182 Uiso 1 1 calc R . .
C3 C 0.0872(8) 0.5723(7) 0.9025(8) 0.135(3) Uani 1 1 d D . .
H3A H 0.0382 0.5223 0.8728 0.203 Uiso 1 1 calc R . .
H3B H 0.0281 0.6233 0.8906 0.203 Uiso 1 1 calc R . .
H3C H 0.1057 0.5631 0.9726 0.203 Uiso 1 1 calc R . .
C4 C 0.1802(12) 0.6074(6) 0.7560(6) 0.152(4) Uani 1 1 d DU . .
H4A H 0.0950 0.5726 0.7374 0.182 Uiso 1 1 calc R . .
H4B H 0.1475 0.6675 0.7575 0.182 Uiso 1 1 calc R . .
C5 C 0.2609(13) 0.6025(5) 0.6777(6) 0.149(5) Uani 1 1 d . . .
H5A H 0.3466 0.6380 0.6918 0.179 Uiso 1 1 calc R . .
H5B H 0.2061 0.6273 0.6201 0.179 Uiso 1 1 calc R . .
C11 C 0.4065(5) 0.3666(4) 0.5025(4) 0.0657(14) Uani 1 1 d . . .
H11A H 0.3920 0.4276 0.4881 0.099 Uiso 1 1 calc R . .
H11B H 0.4838 0.3449 0.4671 0.099 Uiso 1 1 calc R . .
H11C H 0.4306 0.3591 0.5723 0.099 Uiso 1 1 calc R . .
C12 C 0.2941(6) 0.2222(3) 0.4904(4) 0.0598(13) Uani 1 1 d . . .
H12A H 0.3290 0.2132 0.5585 0.090 Uiso 1 1 calc R . .
H12B H 0.3629 0.1997 0.4484 0.090 Uiso 1 1 calc R . .
H12C H 0.2039 0.1924 0.4765 0.090 Uiso 1 1 calc R . .
C13 C 0.2394(5) 0.3314(3) 0.3633(3) 0.0538(12) Uani 1 1 d . . .
H13A H 0.1510 0.3021 0.3416 0.081 Uiso 1 1 calc R . .
H13B H 0.3162 0.3081 0.3286 0.081 Uiso 1 1 calc R . .
H13C H 0.2294 0.3928 0.3496 0.081 Uiso 1 1 calc R . .
C14 C 0.1462(5) 0.3510(3) 0.5233(3) 0.0526(11) Uani 1 1 d . . .
H14A H 0.1383 0.4135 0.5127 0.063 Uiso 1 1 calc R . .
H14B H 0.0591 0.3245 0.4918 0.063 Uiso 1 1 calc R . .
C15 C 0.1516(6) 0.3341(4) 0.6320(4) 0.0623(13) Uani 1 1 d . . .
H15A H 0.2479 0.3455 0.6627 0.075 Uiso 1 1 calc R . .
H15B H 0.0852 0.3729 0.6616 0.075 Uiso 1 1 calc R . .
Cl1 Cl 0.47662(13) 0.68887(9) 0.22403(11) 0.0662(4) Uani 1 1 d . . .
Cl2 Cl 0.07083(14) 0.67206(9) 0.14970(10) 0.0668(4) Uani 1 1 d . . .
Cl3 Cl 0.30375(16) 0.46570(8) 0.15374(10) 0.0632(4) Uani 1 1 d . . .
Cl4 Cl 0.22332(15) 0.58201(9) 0.40281(8) 0.0612(4) Uani 1 1 d . . .

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 0.0383(4) 0.0378(4) 0.0347(4) 0.0000(2) 0.0046(2) -0.0003(3)
F1 0.353(10) 0.134(5) 0.074(3) -0.018(3) 0.043(4) 0.012(5)
F2 0.124(3) 0.084(3) 0.074(2) 0.0135(18) 0.035(2) -0.008(2)
N1 0.066(3) 0.059(3) 0.046(2) 0.0004(18) 0.0078(19) 0.017(2)
N2 0.0446(19) 0.043(2) 0.0329(17) 0.0009(14) 0.0042(14) 0.0038(15)
C1 0.255(13) 0.189(11) 0.138(8) -0.053(8) 0.056(9) -0.173(11)
C2 0.172(8) 0.099(6) 0.093(6) 0.025(4) 0.014(6) 0.053(6)
C3 0.077(5) 0.177(9) 0.153(9) -0.017(7) 0.016(5) -0.005(6)
C4 0.225(11) 0.140(9) 0.096(6) 0.051(6) 0.045(7) 0.080(8)
C5 0.304(16) 0.074(5) 0.079(6) -0.005(4) 0.072(8) 0.004(7)
C11 0.052(3) 0.076(4) 0.067(3) -0.003(3) -0.002(2) -0.018(3)
C12 0.074(3) 0.045(3) 0.062(3) 0.010(2) 0.014(3) 0.016(2)
C13 0.068(3) 0.057(3) 0.036(2) 0.0043(19) 0.001(2) 0.004(2)
C14 0.061(3) 0.050(3) 0.046(3) 0.000(2) 0.007(2) 0.009(2)
C15 0.069(3) 0.068(4) 0.052(3) 0.001(2) 0.015(2) 0.005(3)
Cl1 0.0519(7) 0.0703(9) 0.0774(9) 0.0068(6) 0.0111(6) -0.0197(6)
Cl2 0.0578(7) 0.0766(9) 0.0630(8) 0.0009(6) -0.0099(6) 0.0231(6)
Cl3 0.0850(9) 0.0451(7) 0.0606(8) -0.0141(5) 0.0131(6) 0.0049(6)
Cl4 0.0819(9) 0.0673(8) 0.0364(6) 0.0085(5) 0.0157(6) 0.0075(6)

_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 Cl3 2.3591(13) . ?
Mn1 Cl1 2.3695(13) . ?
Mn1 Cl2 2.3738(13) . ?
Mn1 Cl4 2.3761(14) . ?
F1 C5 1.338(9) . ?
F2 C15 1.385(7) . ?
N1 C1 1.452(9) . ?
N1 C4 1.462(9) . ?
N1 C3 1.461(9) . ?
N1 C2 1.489(8) . ?
N2 C11 1.478(6) . ?
N2 C13 1.485(5) . ?
N2 C12 1.497(5) . ?
N2 C14 1.516(6) . ?
C4 C5 1.359(12) . ?
C14 C15 1.492(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
Cl3 Mn1 Cl1 109.36(6) . . ?
Cl3 Mn1 Cl2 108.03(5) . . ?
Cl1 Mn1 Cl2 107.71(6) . . ?
Cl3 Mn1 Cl4 113.06(5) . . ?
Cl1 Mn1 Cl4 110.37(5) . . ?
Cl2 Mn1 Cl4 108.13(5) . . ?
C1 N1 C4 111.7(7) . . ?
C1 N1 C3 107.1(6) . . ?
C4 N1 C3 103.9(7) . . ?
C1 N1 C2 115.1(7) . . ?
C4 N1 C2 113.0(5) . . ?
C3 N1 C2 105.1(6) . . ?
C11 N2 C13 107.8(4) . . ?
C11 N2 C12 110.5(4) . . ?
C13 N2 C12 108.5(3) . . ?
C11 N2 C14 111.8(4) . . ?
C13 N2 C14 108.1(3) . . ?
C12 N2 C14 110.0(4) . . ?
C5 C4 N1 127.6(9) . . ?
C4 C5 F1 114.3(8) . . ?
C15 C14 N2 116.4(4) . . ?
F2 C15 C14 109.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.75
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         1.217
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.093
