# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1-290K
_database_code_depnum_ccdc_archive 'CCDC 2296134'
loop_
_audit_author_name
_audit_author_address
'Haina Zhang'
;Nanchang University
China
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2023-10-10 downloaded from the CCDC.
;
_audit_creation_date             2023-07-11
_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         'C5 H13 F N, Br4 Fe'
_chemical_formula_sum            'C5 H13 Br4 F Fe N'
_chemical_formula_weight         481.61
_chemical_absolute_configuration ?
_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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
Fe Fe 0.3463 0.8444 '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'

_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           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   15.0498(16)
_cell_length_b                   16.3256(16)
_cell_length_c                   10.7180(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2633.4(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2509
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      29.9810
_cell_measurement_theta_min      2.5450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    13.253
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5579
_diffrn_reflns_point_group_measured_fraction_full 0.897
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         2.495
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'multiwire proportional'
_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         0.700
_reflns_Friedel_fraction_full    0.786
_reflns_Friedel_fraction_max     0.786
_reflns_number_gt                1805
_reflns_number_total             2422
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.738
_refine_diff_density_min         -2.149
_refine_diff_density_rms         0.312
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2173
_refine_ls_number_restraints     89
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.038
_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)+(0.1067P)²+6.4426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.1612
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.94(6)
 0.06(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N1-C3 \\sim N1-C2 \\sim N1-C1 \\sim N1-C4 \\sim C5-C4
 with sigma of 0.0001
4. Uiso/Uaniso restraints and constraints
F1 \\sim N1 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(N1) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(C3) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(F1) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
5.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_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
Br1 Br 0.87281(11) 0.62851(10) 0.4451(7) 0.0153(5) Uani 1 1 d . . . . .
Fe1 Fe 1.000000 0.6140(2) 0.5669(8) 0.0114(8) Uani 1 2 d S T P . .
Br2 Br 1.000000 0.71277(16) 0.7267(7) 0.0198(7) Uani 1 2 d S T P . .
Br3 Br 1.000000 0.48259(16) 0.6556(7) 0.0200(7) Uani 1 2 d S T P . .
Fe2 Fe 0.500000 0.6258(2) 0.5817(8) 0.0107(8) Uani 1 2 d S T P . .
Br4 Br 0.62732(11) 0.61895(11) 0.4566(7) 0.0157(5) Uani 1 1 d . . . . .
Br5 Br 0.500000 0.74922(17) 0.6914(7) 0.0226(6) Uani 1 2 d S T P . .
Br6 Br 0.500000 0.51634(15) 0.7221(7) 0.0209(6) Uani 1 2 d S T P . .
F1 F 0.7499(7) 0.3857(6) 0.2750(15) 0.033(3) Uani 1 1 d . U . . .
N1 N 0.73386(17) 0.36391(16) 0.56484(12) 0.014(3) Uani 1 1 d D U . . .
C1 C 0.7445(9) 0.4412(2) 0.6377(5) 0.016(4) Uani 1 1 d D U . . .
H1A H 0.799791 0.439837 0.682329 0.025 Uiso 1 1 calc GR . . . .
H1B H 0.696321 0.446409 0.695916 0.025 Uiso 1 1 calc GR . . . .
H1C H 0.744201 0.487171 0.581818 0.025 Uiso 1 1 calc GR . . . .
C2 C 0.7373(11) 0.2936(3) 0.6539(4) 0.020(4) Uani 1 1 d D U . . .
H2A H 0.792914 0.294278 0.697603 0.030 Uiso 1 1 calc GR . . . .
H2B H 0.731636 0.243156 0.608572 0.030 Uiso 1 1 calc GR . . . .
H2C H 0.689391 0.298246 0.712657 0.030 Uiso 1 1 calc GR . . . .
C3 C 0.6453(2) 0.3650(10) 0.5021(6) 0.018(4) Uani 1 1 d D U . . .
H3A H 0.599203 0.363522 0.563958 0.027 Uiso 1 1 calc GR . . . .
H3B H 0.640028 0.318124 0.448522 0.027 Uiso 1 1 calc GR . . . .
H3C H 0.639690 0.414096 0.453381 0.027 Uiso 1 1 calc GR . . . .
C4 C 0.8084(3) 0.3540(3) 0.4741(2) 0.019(3) Uani 1 1 d D U . . .
H4A H 0.864157 0.360034 0.518430 0.022 Uiso 1 1 calc R . . . .
H4B H 0.806431 0.298806 0.440557 0.022 Uiso 1 1 calc R . . . .
C5 C 0.8069(13) 0.4133(3) 0.3681(4) 0.025(4) Uani 1 1 d D U . . .
H5A H 0.787123 0.466413 0.397651 0.030 Uiso 1 1 calc R . . . .
H5B H 0.866320 0.419436 0.334445 0.030 Uiso 1 1 calc R . . . .


_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
Br1 Fe1 2.329(3) . ?
Fe1 Br2 2.353(4) . ?
Fe1 Br3 2.347(4) . ?
Fe2 Br4 2.341(3) 4_655 ?
Fe2 Br4 2.341(3) . ?
Fe2 Br5 2.333(4) . ?
Fe2 Br6 2.336(4) . ?
F1 C5 1.391(18) . ?
N1 C1 1.493(2) . ?
N1 C2 1.493(2) . ?
N1 C3 1.493(2) . ?
N1 C4 1.493(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.493(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 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
Br1 Fe1 Br1 110.57(18) 4_755 . ?
Br1 Fe1 Br2 109.77(12) 4_755 . ?
Br1 Fe1 Br2 109.77(12) . . ?
Br1 Fe1 Br3 108.68(11) 4_755 . ?
Br1 Fe1 Br3 108.68(11) . . ?
Br3 Fe1 Br2 109.34(17) . . ?
Br4 Fe2 Br4 109.86(19) . 4_655 ?
Br5 Fe2 Br4 109.24(11) . . ?
Br5 Fe2 Br4 109.24(11) . 4_655 ?
Br5 Fe2 Br6 109.63(18) . . ?
Br6 Fe2 Br4 109.43(11) . . ?
Br6 Fe2 Br4 109.43(11) . 4_655 ?
C1 N1 C2 108.2(3) . . ?
C1 N1 C3 108.7(8) . . ?
C1 N1 C4 110.6(5) . . ?
C3 N1 C2 109.1(8) . . ?
C3 N1 C4 112.2(3) . . ?
C4 N1 C2 107.9(6) . . ?
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 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4A 108.6 . . ?
N1 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 N1 114.4(7) . . ?
C5 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
F1 C5 C4 110.2(9) . . ?
F1 C5 H5A 109.6 . . ?
F1 C5 H5B 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.94(6)
2 0.06(6)

####################################################################### 
# 
# 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_1_320K
_database_code_depnum_ccdc_archive 'CCDC 2296135'
loop_
_audit_author_name
_audit_author_address
'Haina Zhang'
;Nanchang University
China
;
_audit_update_record             
;
2023-10-08 deposited with the CCDC.	2023-10-10 downloaded from the CCDC.
;
_audit_creation_date             2023-10-07
_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         'Br2.16 Fe0.54, 0.46(Br4 Fe), C5 H13 F N'
_chemical_formula_sum            'C5 H13 Br4 F Fe N'
_chemical_formula_weight         481.61
_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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
Fe Fe 0.3463 0.8444 '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'

_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           57
_space_group_name_H-M_alt        'P b c m'
_space_group_name_Hall           '-P 2c 2b'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'-x, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8804(11)
_cell_length_b                   13.614(2)
_cell_length_c                   15.219(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1425.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    771
_cell_measurement_temperature    320
_cell_measurement_theta_max      18.67
_cell_measurement_theta_min      2.96
_shelx_estimated_absorpt_T_max   0.460
_shelx_estimated_absorpt_T_min   0.310
_exptl_absorpt_coefficient_mu    12.241
_exptl_absorpt_correction_T_max  0.613
_exptl_absorpt_correction_T_min  0.485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.244
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0911
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6829
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.677
_diffrn_ambient_temperature      320
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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                490
_reflns_number_total             1312
_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       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.103
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1312
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.1711
_refine_ls_R_factor_gt           0.0741
_refine_ls_restrained_S_all      0.910
_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)+(0.1646P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2209
_refine_ls_wR_factor_ref         0.2916
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5-F1
 1.3 with sigma of 0.05
 N1-C5
 2.515 with sigma of 0.04
 C4-F1
 2.394 with sigma of 0.04
 N1-C12 \\sim N1-C1 \\sim N1-C3 \\sim N1-C4
 with sigma of 0.02
 C1-C12 \\sim C1-C3 \\sim C1-C4 \\sim C12-C3 \\sim C12-C4 \\sim C3-C4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F1 \\sim N1 \\sim C12 \\sim C4 \\sim C1 \\sim C3 \\sim C5: within 2A with sigma
of 0.001 and sigma for terminal atoms of 0.002
Uanis(N1) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C1) \\sim
Ueq, Uanis(C3) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(F1) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 F1, N1, C12, C4, C1, C3, C5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Sof(Br3A)=1-FVAR(1)
 Sof(Fe1A)=Sof(Br4A)=Sof(Br1A)=0.5*(1-FVAR(2))
 Sof(Br4)=Sof(Br1)=Sof(Fe1)=0.5*FVAR(2)
 Sof(Br3)=FVAR(1)
 Fixed Sof: N1(0.5) C12(0.5) H12A(0.5) H12B(0.5) H12C(0.5) C4(0.5) H4A(0.5)
 H4B(0.5) F1(0.5) C5(0.5) H5A(0.5) H5B(0.5) C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5)
 C3(0.5) H3A(0.5) H3B(0.5) H3C(0.5)
6.a Riding coordinates:
 C12(H12A,H12B,H12C), C1(H1A,H1B,H1C), C3(H3A,H3B,H3C)
6.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Br4 Br 1.013(4) 0.525(4) 0.250000 0.150(9) Uani 0.46(7) 2 d S T P A 1
Br1 Br 0.603(6) 0.723(2) 0.250000 0.145(9) Uani 0.46(7) 2 d S T P A 1
Fe1 Fe 0.695(5) 0.561(3) 0.250000 0.085(6) Uani 0.46(7) 2 d S T P A 1
N1 N 0.074(4) 0.751(3) 0.497(3) 0.238(6) Uani 0.5 1 d D U . B -1
C12 C 0.211(8) 0.729(4) 0.420(4) 0.238(6) Uani 0.5 1 d D U . B -1
H12A H 0.135836 0.711359 0.369606 0.356 Uiso 0.5 1 d R . . B -1
H12B H 0.271906 0.671909 0.444276 0.356 Uiso 0.5 1 d R . . B -1
H12C H 0.308126 0.776219 0.403916 0.356 Uiso 0.5 1 d R . . B -1
C4 C 0.003(5) 0.655(3) 0.536(4) 0.238(6) Uani 0.5 1 d D U . B -1
H4A H 0.082564 0.603534 0.510261 0.285 Uiso 0.5 1 calc R . . B -1
H4B H 0.034058 0.656944 0.597784 0.285 Uiso 0.5 1 calc R . . B -1
F1 F -0.318(4) 0.691(2) 0.504(2) 0.239(6) Uani 0.5 1 d D U . B -1
C5 C -0.169(7) 0.626(3) 0.531(4) 0.238(6) Uani 0.5 1 d D U . B -1
H5A H -0.204231 0.599880 0.587820 0.286 Uiso 0.5 1 calc R . . B -1
H5B H -0.170386 0.570626 0.490015 0.286 Uiso 0.5 1 calc R . . B -1
C1 C 0.184(8) 0.808(4) 0.566(5) 0.238(6) Uani 0.5 1 d D U . B -1
H1A H 0.139668 0.809118 0.626270 0.356 Uiso 0.5 1 d R . . B -1
H1B H 0.161488 0.871378 0.540160 0.356 Uiso 0.5 1 d R . . B -1
H1C H 0.320908 0.794038 0.565310 0.356 Uiso 0.5 1 d R . . B -1
C3 C -0.096(6) 0.811(3) 0.464(4) 0.238(6) Uani 0.5 1 d D U . B -1
H3A H -0.053302 0.859219 0.422021 0.356 Uiso 0.5 1 d R . . B -1
H3B H -0.181932 0.841579 0.505551 0.356 Uiso 0.5 1 d R . . B -1
H3C H -0.164172 0.759469 0.433781 0.356 Uiso 0.5 1 d R . . B -1
Br3 Br 0.518(4) 0.474(2) 0.1286(15) 0.126(4) Uani 0.46(7) 1 d . . . A 1
Fe1A Fe 0.642(5) 0.539(2) 0.250000 0.086(5) Uani 0.54(7) 2 d S T P A 2
Br4A Br 0.980(4) 0.498(3) 0.267(4) 0.152(10) Uani 0.27(3) 1 d . . . A 2
Br1A Br 0.656(7) 0.713(2) 0.270(5) 0.169(9) Uani 0.27(3) 1 d . . . A 2
Br3A Br 0.540(4) 0.499(3) 0.1203(14) 0.151(8) Uani 0.54(7) 1 d . . . A 2


_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
Br4 Fe1 2.24(4) . ?
Br1 Fe1 2.29(5) . ?
Fe1 Br3 2.51(4) . ?
Fe1 Br3 2.51(4) 6_556 ?
N1 C12 1.52(3) . ?
N1 C4 1.52(3) . ?
N1 C1 1.52(3) . ?
N1 C3 1.52(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9594 . ?
C12 H12C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.25(4) . ?
F1 C5 1.42(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 H1A 0.9601 . ?
C1 H1B 0.9599 . ?
C1 H1C 0.9601 . ?
C3 H3A 0.9598 . ?
C3 H3B 0.9602 . ?
C3 H3C 0.9598 . ?
Fe1A Br4A 2.40(3) 6_556 ?
Fe1A Br4A 2.40(3) . ?
Fe1A Br1A 2.40(4) 6_556 ?
Fe1A Br1A 2.40(4) . ?
Fe1A Br3A 2.16(3) 6_556 ?
Fe1A Br3A 2.16(3) . ?
Br4A Br4A 0.50(13) 6_556 ?
Br1A Br1A 0.62(14) 6_556 ?

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
Br4 Fe1 Br1 119(2) . . ?
Br4 Fe1 Br3 111.6(14) . 6_556 ?
Br4 Fe1 Br3 111.6(14) . . ?
Br1 Fe1 Br3 108.7(14) . 6_556 ?
Br1 Fe1 Br3 108.7(14) . . ?
Br3 Fe1 Br3 95(2) . 6_556 ?
C4 N1 C12 109.2(12) . . ?
C1 N1 C12 109.0(11) . . ?
C1 N1 C4 109.4(12) . . ?
C3 N1 C12 109.2(12) . . ?
C3 N1 C4 110.0(12) . . ?
C3 N1 C1 109.9(12) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 98.1 . . ?
N1 C12 H12C 120.0 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C4 H4A 106.4 . . ?
N1 C4 H4B 106.4 . . ?
H4A C4 H4B 106.4 . . ?
C5 C4 N1 124(3) . . ?
C5 C4 H4A 106.4 . . ?
C5 C4 H4B 106.4 . . ?
C4 C5 F1 120(3) . . ?
C4 C5 H5A 107.3 . . ?
C4 C5 H5B 107.3 . . ?
F1 C5 H5A 107.3 . . ?
F1 C5 H5B 107.3 . . ?
H5A C5 H5B 106.9 . . ?
N1 C1 H1A 120.5 . . ?
N1 C1 H1B 94.9 . . ?
N1 C1 H1C 111.8 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C3 H3A 110.4 . . ?
N1 C3 H3B 119.3 . . ?
N1 C3 H3C 98.0 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
Br4A Fe1A Br1A 100.3(18) . . ?
Br4A Fe1A Br1A 101.9(18) 6_556 . ?
Br3A Fe1A Br4A 111(2) . . ?
Br3A Fe1A Br4A 99.2(19) 6_556 . ?
Br3A Fe1A Br1A 98(2) 6_556 . ?
Br3A Fe1A Br1A 112(2) . . ?
Br3A Fe1A Br3A 132(4) . 6_556 ?
Br4A Br4A Fe1A 84.0(16) 6_556 . ?
Br1A Br1A Fe1A 82.6(17) 6_556 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C4 C5 F1 -14(9) . . . . ?
C12 N1 C4 C5 -112(6) . . . . ?
C1 N1 C4 C5 129(6) . . . . ?
C3 N1 C4 C5 8(7) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
