# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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
_audit_block_doi                 10.5517/ccdc.csd.cc2f9665
_database_code_depnum_ccdc_archive 'CCDC 2243166'
loop_
_audit_author_name
_audit_author_address
'Fang-Xin Wang'
;University
China
;
_audit_update_record             
;
2023-02-20 deposited with the CCDC.	2023-07-12 downloaded from the CCDC.
;
_audit_creation_date             2022-07-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Fe, 0.5(C16 H28 N2 O2)'
_chemical_formula_sum            'C8 H14 Cl4 Fe N O'
_chemical_formula_weight         337.85
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNFeCl
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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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                   9.1323(5)
_cell_length_b                   10.3481(6)
_cell_length_c                   14.8559(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1403.91(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3000
_cell_measurement_temperature    301.32(10)
_cell_measurement_theta_max      29.7130
_cell_measurement_theta_min      2.6920
_shelx_estimated_absorpt_T_max   0.840
_shelx_estimated_absorpt_T_min   0.713
_exptl_absorpt_coefficient_mu    1.811
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4576
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.738
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.857
_diffrn_reflns_theta_min         2.742
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.32(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.823
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  31.00   0.50    0.43    --    4.95 -84.00 -92.00  138
  2  ω    -56.00 -10.00   0.50    0.43    --   -5.34 -41.00  98.00   92
  3  ω    -18.00  27.00   0.50    0.43    --   -5.34 -99.00-150.00   90
  4  ω    -18.00  11.00   0.50    0.43    --   -5.34 -99.00   0.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0327681000
_diffrn_orient_matrix_UB_12      -0.0507835000
_diffrn_orient_matrix_UB_13      0.0249531000
_diffrn_orient_matrix_UB_21      0.0683446000
_diffrn_orient_matrix_UB_22      0.0324846000
_diffrn_orient_matrix_UB_23      -0.0018841000
_diffrn_orient_matrix_UB_31      -0.0169777000
_diffrn_orient_matrix_UB_32      0.0326625000
_diffrn_orient_matrix_UB_33      0.0406430000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.897
_reflns_Friedel_fraction_max     0.647
_reflns_number_gt                1514
_reflns_number_total             1715
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 603 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1715
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.104
_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)+(0.0421P)²+0.3762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0843
_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. Others
 Fixed Sof: H1B(0.5) H1A(0.5) H7A(0.5) H7B(0.5) H8A(0.5) H8B(0.5) C5(0.5)
 H5A(0.5) H5B(0.5) C6(0.5) H6A(0.5) H6B(0.5) O1(0.5) C3(0.5) C2(0.5) H2A(0.5)
 H2B(0.5)
3.a Riding coordinates:
 C1(H1B,H1A,H1C), C7(H7A,H7B), C8(H8A,H8B), C5(H5A,H5B), C6(H6A,H6B), C2(H2A,
 H2B)
;
_atom_sites_solution_hydrogens   difmap
_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
Fe1 Fe 1.500000 0.62129(6) 0.12843(5) 0.0545(2) Uani 1 2 d S T P . .
Cl1 Cl 1.30591(12) 0.74603(10) 0.12120(9) 0.0829(3) Uani 1 1 d . . . . .
Cl3 Cl 1.500000 0.5223(2) 0.25754(13) 0.1069(8) Uani 1 2 d S T P . .
Cl2 Cl 1.500000 0.4895(2) 0.01382(15) 0.1023(8) Uani 1 2 d S T P . .
N1 N 1.000000 0.5341(3) -0.0968(3) 0.0510(9) Uani 1 2 d S T P . .
C4 C 1.000000 0.3395(7) -0.2031(6) 0.0746(18) Uani 1 2 d S T P . .
C1 C 1.000000 0.6484(8) -0.0340(5) 0.087(2) Uani 1 2 d S T P . .
H1B H 1.085830 0.699695 -0.044747 0.131 Uiso 0.5 1 d R U P A -1
H1A H 0.914170 0.699695 -0.044747 0.131 Uiso 0.5 1 d R U P A -1
H1C H 1.000000 0.618875 0.027253 0.131 Uiso 0.5 1 d R U P A -1
C7 C 1.000000 0.4670(5) -0.2571(4) 0.0695(15) Uani 1 2 d S T P B .
H7A H 0.913270 0.471211 -0.294680 0.083 Uiso 0.5 1 d R U P . .
H7B H 1.086730 0.471211 -0.294680 0.083 Uiso 0.5 1 d R U P . .
C8 C 1.000000 0.5800(6) -0.1916(4) 0.0790(18) Uani 1 2 d S T P B .
H8A H 0.913270 0.632107 -0.201857 0.095 Uiso 0.5 1 d R U P . .
H8B H 1.086730 0.632107 -0.201857 0.095 Uiso 0.5 1 d R U P . .
C5 C 0.856(3) 0.331(3) -0.1460(17) 0.063(4) Uani 0.5 1 d . . P B -1
H5A H 0.768597 0.305410 -0.178899 0.076 Uiso 0.5 1 d R U P B -1
H5B H 0.882107 0.263780 -0.103659 0.076 Uiso 0.5 1 d R U P B -1
C6 C 0.850(3) 0.465(3) -0.0829(19) 0.064(4) Uani 0.5 1 d . . P B -1
H6A H 0.827940 0.450427 -0.019813 0.077 Uiso 0.5 1 d R U P B -1
H6B H 0.770630 0.513707 -0.110283 0.077 Uiso 0.5 1 d R U P B -1
O1 O 1.2210(10) 0.2556(8) -0.1389(7) 0.116(3) Uani 0.5 1 d . . P B -1
C3 C 1.117(4) 0.350(3) -0.142(3) 0.087(7) Uani 0.5 1 d . . P B -1
C2 C 1.117(3) 0.442(3) -0.081(2) 0.079(6) Uani 0.5 1 d . . P B -1
H2A H 1.207230 0.488051 -0.068778 0.095 Uiso 0.5 1 d R U P B -1
H2B H 1.089360 0.391991 -0.028258 0.095 Uiso 0.5 1 d R U P B -1
H4 H 1.000000 0.260(8) -0.243(6) 0.11(3) Uiso 1 2 d S . P . .


_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
Fe1 Cl1 2.1953(10) . ?
Fe1 Cl1 2.1954(10) 4_855 ?
Fe1 Cl3 2.1746(18) . ?
Fe1 Cl2 2.1812(18) . ?
N1 C1 1.506(8) . ?
N1 C8 1.487(7) . ?
N1 C6 1.56(3) . ?
N1 C2 1.45(3) . ?
C4 C7 1.545(9) . ?
C4 C5 1.57(3) . ?
C4 C3 1.41(4) . ?
C4 H4 1.01(9) . ?
C1 H1B 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1C 0.9602 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.521(9) . ?
C8 H8A 0.9701 . ?
C8 H8B 0.9701 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9701 . ?
C5 C6 1.67(4) . ?
C6 H6A 0.9699 . ?
C6 H6B 0.9699 . ?
O1 C3 1.36(2) . ?
C3 C2 1.32(5) . ?
C2 H2A 0.9699 . ?
C2 H2B 0.9701 . ?

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
Cl1 Fe1 Cl1 107.68(7) . 4_855 ?
Cl3 Fe1 Cl1 108.68(5) . 4_855 ?
Cl3 Fe1 Cl1 108.68(5) . . ?
Cl3 Fe1 Cl2 113.20(10) . . ?
Cl2 Fe1 Cl1 109.23(6) . . ?
Cl2 Fe1 Cl1 109.23(6) . 4_855 ?
C1 N1 C6 106.2(10) . . ?
C8 N1 C1 109.6(5) . . ?
C8 N1 C6 105.7(11) . . ?
C2 N1 C1 114.5(12) . . ?
C2 N1 C8 111.4(13) . . ?
C2 N1 C6 108.9(8) . . ?
C7 C4 C5 109.1(11) . . ?
C7 C4 H4 113(5) . . ?
C5 C4 H4 106(3) . . ?
C3 C4 C7 105.6(15) . . ?
C3 C4 C5 107.2(10) . . ?
C3 C4 H4 116(3) . . ?
N1 C1 H1B 109.4 . . ?
N1 C1 H1A 109.4 . . ?
N1 C1 H1C 109.7 . . ?
H1B C1 H1A 109.5 . . ?
H1B C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
C4 C7 H7A 109.7 . . ?
C4 C7 H7B 109.7 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 C4 108.9(5) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
N1 C8 C7 111.1(4) . . ?
N1 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 109.5 . . ?
C4 C5 H5A 115.6 . . ?
C4 C5 H5B 100.4 . . ?
C4 C5 C6 106.6(16) . . ?
H5A C5 H5B 109.5 . . ?
C6 C5 H5A 118.9 . . ?
C6 C5 H5B 103.8 . . ?
N1 C6 C5 106.1(15) . . ?
N1 C6 H6A 112.2 . . ?
N1 C6 H6B 111.1 . . ?
C5 C6 H6A 114.9 . . ?
C5 C6 H6B 102.7 . . ?
H6A C6 H6B 109.5 . . ?
O1 C3 C4 120(3) . . ?
C2 C3 C4 120(2) . . ?
C2 C3 O1 120(3) . . ?
N1 C2 H2A 109.6 . . ?
N1 C2 H2B 107.1 . . ?
C3 C2 N1 111(2) . . ?
C3 C2 H2A 118.6 . . ?
C3 C2 H2B 99.8 . . ?
H2A C2 H2B 109.5 . . ?

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
C4 C7 C8 N1 0.000(0) . . . . ?
C4 C5 C6 N1 -8(2) . . . . ?
C4 C3 C2 N1 -9(4) . . . . ?
C1 N1 C8 C7 180.000(0) . . . . ?
C1 N1 C6 C5 -175.3(14) . . . . ?
C1 N1 C2 C3 -175(2) . . . . ?
C7 C4 C5 C6 -55.8(17) . . . . ?
C7 C4 C3 O1 -126(3) . . . . ?
C7 C4 C3 C2 62(3) . . . . ?
C8 N1 C6 C5 68.3(16) . . . . ?
C8 N1 C2 C3 -50(2) . . . . ?
C5 C4 C7 C8 62.7(10) . . . . ?
C5 C4 C3 O1 117(3) . . . . ?
C5 C4 C3 C2 -54(3) . . . . ?
C6 N1 C8 C7 -65.9(10) . . . . ?
C6 N1 C2 C3 66(2) . . . . ?
O1 C3 C2 N1 179(2) . . . . ?
C3 C4 C7 C8 -52.2(13) . . . . ?
C3 C4 C5 C6 58.1(14) . . . . ?
C2 N1 C8 C7 52.2(10) . . . . ?
C2 N1 C6 C5 -51.5(15) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.340
_oxdiff_exptl_absorpt_empirical_full_min 0.672
