# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_C6H9N2FeCl4
_database_code_depnum_ccdc_archive 'CCDC 2223635'
loop_
_audit_author_name
_audit_author_address
'Jerome Lhoste'
;IMMM
France
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT110_C6H9N2FeCl4         
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: no
;
_vrf_PLAT112_C6H9N2FeCl4         
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       c/2        100 %Fit
RESPONSE: A resolution in the space group P21/m does not allow to have an order in the organic molecule
;
_vrf_PLAT113_C6H9N2FeCl4         
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group      P21/m Check
RESPONSE: A resolution in the space group P21/m does not allow to have an order in the organic molecule
;
# Added during the CSD deposition process: Wednesday 30 November 2022 07:54 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H9 Cl4 Fe N2'
_chemical_formula_weight         306.80

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'
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'

_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                   6.4063(4)
_cell_length_b                   14.2730(9)
_cell_length_c                   13.2376(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.298(3)
_cell_angle_gamma                90
_cell_volume                     1210.39(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    208
_cell_measurement_theta_min      6.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   0.561
_exptl_transmission_factor_max   0.745
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.103
_exptl_absorpt_coefficient_mu    2.087
_exptl_absorpt_process_details   '(SHELX76; Sheldrick, 2008)'
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_exptl_special_details           
;
 ? 
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            16901
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.098
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2783
_reflns_number_gt                1710
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0391P)²+0.5651P] 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         2783
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Fe1 Fe 0.20100(6) 0.25170(2) 0.35608(3) 0.04921(15) Uani 1 1 d . . . . .
Cl1 Cl 0.54206(11) 0.25302(5) 0.36288(7) 0.0630(2) Uani 1 1 d . . . . .
Cl2 Cl 0.07888(12) 0.37665(5) 0.43178(7) 0.0720(2) Uani 1 1 d . . . . .
Cl3 Cl 0.09523(11) 0.12205(5) 0.42993(6) 0.0645(2) Uani 1 1 d . . . . .
Cl4 Cl 0.09194(15) 0.25417(6) 0.19792(6) 0.0772(3) Uani 1 1 d . . . . .
N1 N 0.6555(6) 0.3670(2) 0.0818(2) 0.1022(11) Uani 1 1 d . . . . .
H1A H 0.774953 0.339858 0.086687 0.123 Uiso 1 1 calc R U . . .
H1B H 0.577037 0.356891 0.030056 0.123 Uiso 1 1 calc R U . . .
N2 N 0.7138(4) 0.44036(16) 0.2351(2) 0.0642(7) Uani 1 1 d . . . . .
H2 H 0.832049 0.411942 0.238357 0.077 Uiso 1 1 calc R U . . .
C1 C 0.5915(6) 0.4250(2) 0.1550(2) 0.0660(8) Uani 1 1 d . . . . .
C2 C 0.4003(5) 0.4723(2) 0.1524(3) 0.0711(9) Uani 1 1 d . . . . .
H2A H 0.309641 0.464141 0.098019 0.085 Uiso 1 1 calc R U . . .
C3 C 0.3477(5) 0.5299(2) 0.2291(3) 0.0669(8) Uani 1 1 d . . . . .
H3 H 0.219459 0.560406 0.226776 0.080 Uiso 1 1 calc R U . . .
C4 C 0.4780(5) 0.54500(19) 0.3109(2) 0.0585(7) Uani 1 1 d . . . . .
C5 C 0.4163(6) 0.6085(2) 0.3963(3) 0.0888(11) Uani 1 1 d . . . . .
H5A H 0.509593 0.599123 0.452365 0.133 Uiso 1 1 calc R U . . .
H5B H 0.276200 0.594268 0.416564 0.133 Uiso 1 1 calc R U . . .
H5C H 0.423807 0.672492 0.374411 0.133 Uiso 1 1 calc R U . . .
C6 C 0.6610(4) 0.4985(2) 0.3117(2) 0.0596(7) Uani 1 1 d . . . . .
H6 H 0.752619 0.506548 0.365779 0.072 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
Fe1 0.0471(2) 0.0531(2) 0.0473(3) 0.00098(17) -0.00288(17) 0.00124(16)
Cl1 0.0459(4) 0.0667(5) 0.0765(5) 0.0003(4) 0.0037(3) -0.0009(3)
Cl2 0.0653(5) 0.0710(5) 0.0797(6) -0.0149(4) -0.0075(4) 0.0216(4)
Cl3 0.0648(4) 0.0639(4) 0.0649(5) 0.0113(4) -0.0036(4) -0.0098(3)
Cl4 0.0864(6) 0.0991(7) 0.0461(5) 0.0044(4) -0.0124(4) -0.0006(4)
N1 0.142(3) 0.082(2) 0.084(2) -0.0206(18) 0.020(2) -0.0136(19)
N2 0.0619(15) 0.0562(14) 0.0746(18) 0.0063(13) 0.0001(14) 0.0081(12)
C1 0.093(2) 0.0467(16) 0.059(2) 0.0026(15) 0.0048(18) -0.0193(16)
C2 0.079(2) 0.070(2) 0.064(2) 0.0118(18) -0.0241(18) -0.0196(18)
C3 0.0570(18) 0.0642(18) 0.079(2) 0.0119(18) -0.0117(16) 0.0006(14)
C4 0.0633(18) 0.0515(16) 0.0606(19) 0.0061(14) -0.0054(15) -0.0003(13)
C5 0.102(3) 0.078(2) 0.086(3) -0.015(2) 0.007(2) 0.011(2)
C6 0.0628(18) 0.0562(16) 0.0598(19) 0.0062(15) -0.0136(15) 0.0011(14)

_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 2.1864(8) . ?
Fe1 Cl2 2.1921(8) . ?
Fe1 Cl3 2.2014(8) . ?
Fe1 Cl4 2.2039(9) . ?
N1 C1 1.339(4) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C1 1.334(4) . ?
N2 C6 1.355(4) . ?
N2 H2 0.8600 . ?
C1 C2 1.399(4) . ?
C2 C3 1.351(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.380(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.347(4) . ?
C4 C5 1.503(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6 0.9300 . ?

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 Cl2 109.46(3) . . ?
Cl1 Fe1 Cl3 107.38(3) . . ?
Cl2 Fe1 Cl3 111.68(4) . . ?
Cl1 Fe1 Cl4 110.54(4) . . ?
Cl2 Fe1 Cl4 108.01(3) . . ?
Cl3 Fe1 Cl4 109.79(3) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 C6 123.2(3) . . ?
C1 N2 H2 118.4 . . ?
C6 N2 H2 118.4 . . ?
N2 C1 N1 119.7(3) . . ?
N2 C1 C2 116.8(3) . . ?
N1 C1 C2 123.5(3) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C6 C4 C3 116.9(3) . . ?
C6 C4 C5 121.5(3) . . ?
C3 C4 C5 121.6(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 N2 121.1(3) . . ?
C4 C6 H6 119.5 . . ?
N2 C6 H6 119.5 . . ?

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
C6 N2 C1 N1 179.4(3) . . . . ?
C6 N2 C1 C2 -0.1(4) . . . . ?
N2 C1 C2 C3 -0.2(4) . . . . ?
N1 C1 C2 C3 -179.7(3) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
C2 C3 C4 C6 -0.8(4) . . . . ?
C2 C3 C4 C5 -179.3(3) . . . . ?
C3 C4 C6 N2 0.4(4) . . . . ?
C5 C4 C6 N2 179.0(3) . . . . ?
C1 N2 C6 C4 0.0(4) . . . . ?

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.058

_shelx_res_file                  
;
TITL C6H9N2FeCl4_b.res in P2(1)/m
    C6H9N2FeCl4.res
    created by SHELXL-2018/3 at 16:04:24 on 29-Nov-2022
CELL 0.71073 6.4063 14.2730 13.2376 90.000 90.298 90.000
ZERR 4.00 0.0004 0.0009 0.0010 0.000 0.003 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C H N CL FE
UNIT 24 36 8 16 4
TEMP 23.000
ACTA
L.S. 10
FMAP 2
PLAN 20
HTAB
BOND $H
CONF
WGHT    0.039100    0.565100
FVAR       0.45820
FE1   5    0.201000    0.251700    0.356077    11.00000    0.04711    0.05315 =
         0.04733    0.00098   -0.00288    0.00124
CL1   4    0.542061    0.253017    0.362882    11.00000    0.04587    0.06669 =
         0.07653    0.00031    0.00367   -0.00087
CL2   4    0.078876    0.376653    0.431781    11.00000    0.06532    0.07097 =
         0.07971   -0.01491   -0.00748    0.02161
CL3   4    0.095231    0.122054    0.429935    11.00000    0.06476    0.06387 =
         0.06485    0.01130   -0.00358   -0.00984
CL4   4    0.091939    0.254172    0.197922    11.00000    0.08644    0.09912 =
         0.04605    0.00438   -0.01236   -0.00056
N1    3    0.655455    0.366989    0.081847    11.00000    0.14154    0.08172 =
         0.08368   -0.02061    0.01979   -0.01357
AFIX  93
H1A   2    0.774953    0.339858    0.086687    11.00000   -1.20000
H1B   2    0.577037    0.356891    0.030056    11.00000   -1.20000
AFIX   0
N2    3    0.713827    0.440360    0.235138    11.00000    0.06193    0.05621 =
         0.07456    0.00632    0.00013    0.00810
AFIX  43
H2    2    0.832049    0.411942    0.238357    11.00000   -1.20000
AFIX   0
C1    1    0.591483    0.424965    0.154963    11.00000    0.09268    0.04666 =
         0.05865    0.00259    0.00483   -0.01926
C2    1    0.400290    0.472313    0.152410    11.00000    0.07863    0.06992 =
         0.06442    0.01181   -0.02407   -0.01957
AFIX  43
H2A   2    0.309641    0.464141    0.098019    11.00000   -1.20000
AFIX   0
C3    1    0.347684    0.529912    0.229115    11.00000    0.05703    0.06423 =
         0.07934    0.01190   -0.01173    0.00060
AFIX  43
H3    2    0.219459    0.560406    0.226776    11.00000   -1.20000
AFIX   0
C4    1    0.478002    0.544997    0.310857    11.00000    0.06331    0.05152 =
         0.06058    0.00613   -0.00542   -0.00027
C5    1    0.416330    0.608451    0.396264    11.00000    0.10235    0.07823 =
         0.08598   -0.01494    0.00687    0.01150
AFIX 137
H5A   2    0.509593    0.599123    0.452365    11.00000   -1.50000
H5B   2    0.276200    0.594268    0.416564    11.00000   -1.50000
H5C   2    0.423807    0.672492    0.374411    11.00000   -1.50000
AFIX   0
C6    1    0.661020    0.498549    0.311731    11.00000    0.06278    0.05618 =
         0.05977    0.00624   -0.01358    0.00114
AFIX  43
H6    2    0.752619    0.506548    0.365779    11.00000   -1.20000
AFIX   0
HKLF 4 1 1 0 0 0 1 0 0 0 1




REM  C6H9N2FeCl4_b.res in P2(1)/m
REM wR2 = 0.103213, GooF = S = 1.03234, Restrained GooF = 1.03234 for all data
REM R1 = 0.031996 for 1710 Fo > 4sig(Fo) and 0.063401 for all 2783 data
REM 119 parameters refined using 0 restraints

END

WGHT      0.0387      0.5608

REM Instructions for potential hydrogen bonds
EQIV $1 x+1, -y+1/2, z-1/2
HTAB N1 Cl3_$1
EQIV $2 x+1, y, z
HTAB N1 Cl4_$2
EQIV $3 x, -y+1/2, z-1/2
HTAB N1 Cl1_$3
HTAB N2 Cl4_$2
HTAB C2 Cl3_$3
HTAB C6 Cl2_$2

REM Highest difference peak  0.290,  deepest hole -0.332,  1-sigma level  0.058
Q1    1   0.2150  0.2531  0.1990  11.00000  0.05    0.29
Q2    1   0.0177  0.3340  0.4455  11.00000  0.05    0.24
Q3    1   0.1331  0.2030  0.2133  11.00000  0.05    0.21
Q4    1   0.1788  0.2804  0.2144  11.00000  0.05    0.21
Q5    1   0.6401  0.7460  0.4196  11.00000  0.05    0.21
Q6    1   0.1855  0.1367  0.4561  11.00000  0.05    0.20
Q7    1   0.0449  0.2458  0.2337  11.00000  0.05    0.20
Q8    1   0.0395  0.2609  0.1873  11.00000  0.05    0.20
Q9    1   0.5030  0.4693  0.1663  11.00000  0.05    0.19
Q10   1   0.1559  0.3720  0.4553  11.00000  0.05    0.19
Q11   1   1.0973  0.3961  0.2035  11.00000  0.05    0.17
Q12   1   0.6667  0.6848  0.4201  11.00000  0.05    0.17
Q13   1   0.3245  0.2577  0.5085  11.00000  0.05    0.17
Q14   1   0.0363  0.1564  0.4406  11.00000  0.05    0.16
Q15   1   0.4207  0.2847  0.0582  11.00000  0.05    0.16
Q16   1   0.5501  0.6998  0.4416  11.00000  0.05    0.16
Q17   1   0.3198  0.4783  0.2012  11.00000  0.05    0.16
Q18   1   0.1143  0.3764  0.3844  11.00000  0.05    0.15
Q19   1   0.9000  0.6074  0.3055  11.00000  0.05    0.15
Q20   1   0.4833  0.5180  0.5360  11.00000  0.05    0.15
;
_shelx_res_checksum              2654
