# 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 2020

####################################################################### 
# 
# 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_180410-yxq-feietn
_database_code_depnum_ccdc_archive 'CCDC 1963446'
loop_
_audit_author_name
_audit_author_address
'Zhiyin Xiao'
;Jiaxing University
China
;
_audit_update_record             
;
2019-11-02 deposited with the CCDC.	2020-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-10-28
_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        'salt 1'
_chemical_formula_moiety         'C3 Fe I3 O3, C2 H8 N'
_chemical_formula_sum            'C5 H8 Fe I3 N O3'
_chemical_formula_weight         566.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Fe I'
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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.2096(8)
_cell_length_b                   14.5251(12)
_cell_length_c                   10.4460(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.739(7)
_cell_angle_gamma                90
_cell_volume                     1396.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1318
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0790
_cell_measurement_theta_min      3.3790
_shelx_estimated_absorpt_T_max   0.485
_shelx_estimated_absorpt_T_min   0.129
_exptl_absorpt_coefficient_mu    7.692
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            dark-red
_exptl_crystal_density_diffrn    2.695
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       sheet
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5959
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.545
_diffrn_reflns_theta_min         2.805
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  17.00   1.00   12.56    --  -15.89 -99.00 -90.00   31
  2  ω      2.00  70.00   1.00   12.56    --   16.05  57.00  30.00   68
  3  ω     18.00  70.00   1.00   12.56    --   16.05  57.00  90.00   52
  4  ω    -45.00   5.00   1.00   12.56    --   16.05 -57.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0069621000
_diffrn_orient_matrix_UB_12      -0.0484397000
_diffrn_orient_matrix_UB_13      -0.0058771000
_diffrn_orient_matrix_UB_21      0.0762011000
_diffrn_orient_matrix_UB_22      -0.0038550000
_diffrn_orient_matrix_UB_23      -0.0066137000
_diffrn_orient_matrix_UB_31      0.0091983000
_diffrn_orient_matrix_UB_32      -0.0046044000
_diffrn_orient_matrix_UB_33      0.0673697000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1877
_reflns_number_total             3229
_reflns_odcompleteness_completeness 99.23
_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 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.146
_refine_diff_density_min         -0.856
_refine_diff_density_rms         0.188
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0631
_refine_ls_restrained_S_all      1.030
_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)+(0.0620P)²+7.0530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1687
_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, All N(H,H,H) groups
2. Restrained distances
 N1-C4
 1.45 with sigma of 0.001
 C4-C5
 1.55 with sigma of 0.001
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.b Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_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
I1 I 0.04023(9) 0.56540(7) 0.74735(8) 0.0656(3) Uani 1 1 d . . . . .
I2 I 0.45661(9) 0.54319(7) 0.78542(9) 0.0707(3) Uani 1 1 d . . . . .
I3 I 0.21062(12) 0.35067(7) 0.91062(9) 0.0773(4) Uani 1 1 d . . . . .
Fe1 Fe 0.24026(18) 0.44028(12) 0.69200(16) 0.0523(5) Uani 1 1 d . . . . .
O1 O 0.4591(12) 0.3053(9) 0.6359(12) 0.104(4) Uani 1 1 d . . . . .
O3 O 0.2773(13) 0.5432(8) 0.4532(10) 0.095(4) Uani 1 1 d . . . . .
O2 O -0.0004(11) 0.3252(8) 0.5964(10) 0.082(3) Uani 1 1 d . . . . .
N1 N 0.2149(14) 0.5711(8) 0.0697(12) 0.082(4) Uani 1 1 d D . . . .
H1A H 0.304094 0.552955 0.050959 0.124 Uiso 1 1 calc GR . . . .
H1B H 0.161760 0.577664 -0.002289 0.124 Uiso 1 1 calc GR . . . .
H1C H 0.174153 0.529212 0.119283 0.124 Uiso 1 1 calc GR . . . .
C3 C 0.2619(13) 0.5041(11) 0.5458(13) 0.065(4) Uani 1 1 d . . . . .
C2 C 0.0914(15) 0.3706(11) 0.6331(13) 0.066(4) Uani 1 1 d . . . . .
C1 C 0.3748(15) 0.3573(12) 0.6554(14) 0.074(4) Uani 1 1 d . . . . .
C4 C 0.223(2) 0.6585(9) 0.1368(17) 0.140(9) Uani 1 1 d D . . . .
H4A H 0.260069 0.648717 0.223565 0.168 Uiso 1 1 calc R . . . .
H4B H 0.126185 0.684676 0.141361 0.168 Uiso 1 1 calc R . . . .
C5 C 0.323(2) 0.7264(12) 0.067(2) 0.149(9) Uani 1 1 d D . . . .
H5A H 0.422777 0.710530 0.085133 0.223 Uiso 1 1 calc GR . . . .
H5B H 0.305220 0.787974 0.095925 0.223 Uiso 1 1 calc GR . . . .
H5C H 0.303486 0.722847 -0.023784 0.223 Uiso 1 1 calc GR . . . .

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
I1 0.0623(5) 0.0663(6) 0.0685(6) -0.0009(4) 0.0082(4) 0.0124(4)
I2 0.0584(5) 0.0670(6) 0.0864(7) -0.0094(5) -0.0011(4) -0.0052(4)
I3 0.0947(8) 0.0670(7) 0.0698(6) 0.0159(5) -0.0040(5) -0.0030(5)
Fe1 0.0520(10) 0.0519(11) 0.0531(10) -0.0041(8) 0.0029(7) 0.0023(8)
O1 0.083(8) 0.100(9) 0.128(10) -0.035(8) 0.001(7) 0.030(7)
O3 0.122(9) 0.098(9) 0.066(6) 0.015(6) 0.021(6) -0.001(7)
O2 0.075(7) 0.091(8) 0.081(7) -0.011(6) 0.000(5) -0.008(6)
N1 0.091(9) 0.069(9) 0.088(9) -0.019(7) 0.011(7) -0.015(7)
C3 0.053(7) 0.084(11) 0.058(8) -0.007(8) 0.001(6) 0.016(7)
C2 0.062(9) 0.077(10) 0.059(8) 0.004(7) 0.005(6) 0.009(7)
C1 0.051(8) 0.098(13) 0.074(9) -0.031(8) -0.005(7) -0.013(8)
C4 0.091(14) 0.21(3) 0.122(17) 0.023(18) 0.036(12) 0.008(16)
C5 0.16(2) 0.085(16) 0.19(2) -0.010(16) -0.051(19) -0.014(15)

_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
I1 Fe1 2.6637(19) . ?
I2 Fe1 2.6531(19) . ?
I3 Fe1 2.650(2) . ?
Fe1 C3 1.803(15) . ?
Fe1 C2 1.798(16) . ?
Fe1 C1 1.779(16) . ?
O1 C1 1.106(16) . ?
O3 C3 1.134(16) . ?
O2 C2 1.130(16) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C4 1.4501(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.5498(10) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

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
I2 Fe1 I1 93.00(6) . . ?
I3 Fe1 I1 93.33(6) . . ?
I3 Fe1 I2 93.19(6) . . ?
C3 Fe1 I1 85.9(4) . . ?
C3 Fe1 I2 85.4(4) . . ?
C3 Fe1 I3 178.4(5) . . ?
C2 Fe1 I1 86.2(4) . . ?
C2 Fe1 I2 178.4(4) . . ?
C2 Fe1 I3 85.5(4) . . ?
C2 Fe1 C3 95.9(6) . . ?
C1 Fe1 I1 179.6(4) . . ?
C1 Fe1 I2 86.6(4) . . ?
C1 Fe1 I3 86.7(5) . . ?
C1 Fe1 C3 94.1(7) . . ?
C1 Fe1 C2 94.2(6) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C4 N1 H1A 109.5 . . ?
C4 N1 H1B 109.5 . . ?
C4 N1 H1C 109.5 . . ?
O3 C3 Fe1 178.8(13) . . ?
O2 C2 Fe1 178.6(14) . . ?
O1 C1 Fe1 178.2(15) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 C5 110.5(13) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

_shelx_res_file                  
;
TITL 180410-YXQ-FEIEtN in P21/c #14
    180410-yxq-feietn.res
    created by SHELXL-2018/3 at 21:22:02 on 28-Oct-2019
CELL 0.71073 9.20964 14.52505 10.44603 90 91.7386 90
ZERR 4 0.00083 0.00123 0.00085 0 0.0068 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Fe I N O
UNIT 20 32 4 12 4 12
DFIX 1.45 0.001 N1 C4
DFIX 1.55 0.001 C4 C5

L.S. 4
PLAN  0
SIZE 0.45 0.25 0.11
BOND
fmap 2
acta
conf
bond $h
OMIT -1 6 2
OMIT 1 8 1
OMIT 3 2 1
OMIT 3 1 1
OMIT -4 4 1
OMIT -4 0 2
OMIT 1 2 3
OMIT -3 4 2
OMIT 1 0 8
REM <olex2.extras>
REM <HklSrc "%.\\180410-YXQ-FEIEtN.hkl">
REM </olex2.extras>

WGHT    0.062000    7.053000
FVAR       2.67069
I1    4    0.040229    0.565399    0.747346    11.00000    0.06229    0.06630 =
         0.06846   -0.00092    0.00821    0.01243
I2    4    0.456610    0.543195    0.785415    11.00000    0.05841    0.06700 =
         0.08638   -0.00938   -0.00108   -0.00515
I3    4    0.210623    0.350671    0.910621    11.00000    0.09470    0.06703 =
         0.06981    0.01585   -0.00399   -0.00299
FE1   3    0.240260    0.440278    0.692004    11.00000    0.05195    0.05186 =
         0.05309   -0.00412    0.00287    0.00227
O1    6    0.459066    0.305268    0.635885    11.00000    0.08283    0.09967 =
         0.12801   -0.03521    0.00142    0.03006
O3    6    0.277302    0.543205    0.453240    11.00000    0.12181    0.09811 =
         0.06554    0.01460    0.02071   -0.00127
O2    6   -0.000418    0.325192    0.596431    11.00000    0.07468    0.09084 =
         0.08136   -0.01063   -0.00024   -0.00829
N1    5    0.214940    0.571147    0.069707    11.00000    0.09062    0.06938 =
         0.08795   -0.01906    0.01105   -0.01531
AFIX 137
H1A   2    0.304094    0.552955    0.050959    11.00000   -1.50000
H1B   2    0.161760    0.577664   -0.002289    11.00000   -1.50000
H1C   2    0.174153    0.529212    0.119283    11.00000   -1.50000
AFIX   0

C3    1    0.261918    0.504105    0.545822    11.00000    0.05322    0.08450 =
         0.05798   -0.00727    0.00141    0.01563
C2    1    0.091440    0.370550    0.633107    11.00000    0.06219    0.07720 =
         0.05911    0.00407    0.00475    0.00930
C1    1    0.374811    0.357261    0.655449    11.00000    0.05065    0.09840 =
         0.07372   -0.03084   -0.00519   -0.01290
C4    1    0.222783    0.658497    0.136788    11.00000    0.09061    0.20925 =
         0.12226    0.02252    0.03553    0.00786
AFIX  23
H4A   2    0.260069    0.648717    0.223565    11.00000   -1.20000
H4B   2    0.126185    0.684676    0.141361    11.00000   -1.20000
AFIX   0
C5    1    0.323112    0.726425    0.066863    11.00000    0.16339    0.08540 =
         0.19451   -0.01030   -0.05096   -0.01360
AFIX 137
H5A   2    0.422777    0.710530    0.085133    11.00000   -1.50000
H5B   2    0.305220    0.787974    0.095925    11.00000   -1.50000
H5C   2    0.303486    0.722847   -0.023784    11.00000   -1.50000
AFIX   0
HKLF 4




REM  180410-YXQ-FEIEtN in P21/c #14
REM wR2 = 0.1687, GooF = S = 1.030, Restrained GooF = 1.030 for all data
REM R1 = 0.0631 for 1877 Fo > 4sig(Fo) and 0.1131 for all 3229 data
REM 120 parameters refined using 2 restraints

END

WGHT      0.0620      7.0549

REM Highest difference peak  1.146,  deepest hole -0.856,  1-sigma level  0.188
Q1    1   0.3192  0.3511  0.8780  11.00000  0.05    1.15
Q2    1   0.4981  0.5536  0.7131  11.00000  0.05    1.11
Q3    1   0.0558  0.5435  0.8318  11.00000  0.05    1.10
Q4    1   0.1741  0.7083  0.0662  11.00000  0.05    0.77
Q5    1   0.3634  0.5602  0.7425  11.00000  0.05    0.75
Q6    1   0.2212  0.2972  0.8630  11.00000  0.05    0.75
Q7    1   0.2651  0.6604  0.0386  11.00000  0.05    0.74
Q8    1   0.2828  0.6594  0.0858  11.00000  0.05    0.73
Q9    1   0.4948  0.5971  0.7224  11.00000  0.05    0.69
Q10   1   0.4072  0.6012  0.7844  11.00000  0.05    0.68
Q11   1   0.4595  0.3230  0.5476  11.00000  0.05    0.66
Q12   1   0.1951  0.3528  0.6379  11.00000  0.05    0.65
Q13   1  -0.0397  0.6333  0.7944  11.00000  0.05    0.63
Q14   1  -0.0805  0.5600  0.7436  11.00000  0.05    0.62
Q15   1   0.0173  0.6637  0.6956  11.00000  0.05    0.61
Q16   1   0.2526  0.5196  0.7313  11.00000  0.05    0.60
Q17   1   0.2423  0.4333  0.9381  11.00000  0.05    0.59
Q18   1   0.2719  0.4263  0.8003  11.00000  0.05    0.59
Q19   1   0.2372  0.7211  0.2192  11.00000  0.05    0.55
Q20   1   0.1057  0.6535  0.0646  11.00000  0.05    0.55
;
_shelx_res_checksum              46971
_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 3.360
_oxdiff_exptl_absorpt_empirical_full_min 0.725
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/Hexane'
_chemical_properties_physical    
Moisture-sensitive,Heat-sensitive,Light-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_180624-yxq-feic4ni
_database_code_depnum_ccdc_archive 'CCDC 1963448'
loop_
_audit_author_name
_audit_author_address
'Zhiyin Xiao'
;Jiaxing University
China
;
_audit_update_record             
;
2019-11-02 deposited with the CCDC.	2020-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-10-28
_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        'salt 3'
_chemical_formula_moiety         'C3 Fe I3 O3, 0.5(C8 H24 N2)'
_chemical_formula_sum            'C7 H12 Fe I3 N O3'
_chemical_formula_weight         594.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         'H C N O Fe I'
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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   8.2405(9)
_cell_length_b                   8.0958(9)
_cell_length_c                   12.6129(12)
_cell_angle_alpha                90
_cell_angle_beta                 106.5710(10)
_cell_angle_gamma                90
_cell_volume                     806.50(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1448
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.2230
_cell_measurement_theta_min      3.6650
_shelx_estimated_absorpt_T_max   0.732
_shelx_estimated_absorpt_T_min   0.204
_exptl_absorpt_coefficient_mu    6.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    2.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4931
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.370
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  42.00   0.80   30.00    --  -15.89  77.00 -60.00   45
  2  ω    -41.00  44.60   0.80   30.00    --  -15.89  77.00-180.00  107
  3  ω     18.00  45.20   0.80   30.00    --  -15.89  77.00-150.00   34
  4  ω    -11.00  39.40   0.80   30.00    --   16.05  77.00  60.00   63
  5  ω    -11.00  67.40   0.80   30.00    --   16.05  77.00 -60.00   98
  6  ω      9.00  83.40   0.80   30.00    --   16.05  77.00  90.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0553024000
_diffrn_orient_matrix_UB_12      0.0008933000
_diffrn_orient_matrix_UB_13      -0.0545739000
_diffrn_orient_matrix_UB_21      0.0705299000
_diffrn_orient_matrix_UB_22      -0.0061079000
_diffrn_orient_matrix_UB_23      -0.0214287000
_diffrn_orient_matrix_UB_31      -0.0054624000
_diffrn_orient_matrix_UB_32      -0.0874598000
_diffrn_orient_matrix_UB_33      0.0009563000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                935
_reflns_number_total             1515
_reflns_odcompleteness_completeness 99.72
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.080
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1515
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.037
_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)+(0.0844P)²+0.1939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1711
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C6-C5 = C4-C3
 1.55 with sigma of 0.001
 C5-C4
 1.55 with sigma of 0.001
 C3-N1
 1.45 with sigma of 0.001
3. Rigid body (RIGU) restrains
 C6, C5, C4, C3, N1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(I2A)=1-FVAR(1)
 Sof(I2)=FVAR(1)
 Fixed Sof: H5A(0.5) H5B(0.5) H4A(0.5) H4B(0.5) H3A(0.5) H3B(0.5) H1A(0.5)
 H1B(0.5) H1C(0.5) H6A(0.5) H6B(0.5) H6C(0.5)
5.a Riding coordinates:
 N1(H1A,H1B,H1C), C6(H6A,H6B,H6C)
5.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C3(H3A,H3B)
;
_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
C1 C 0.268(2) 0.250000 0.6895(16) 0.125(6) Uani 1 2 d S T P B .
C2 C -0.0099(14) 0.0883(18) 0.6554(10) 0.119(4) Uani 1 1 d . . . . .
C5 C 0.537(3) 0.250000 0.3651(17) 0.282(18) Uani 1 2 d DS TU P . .
H5A H 0.591552 0.345948 0.344257 0.338 Uiso 0.5 1 calc R . . . .
H5B H 0.591552 0.154052 0.344257 0.338 Uiso 0.5 1 calc R . . . .
C4 C 0.353(3) 0.250000 0.2890(16) 0.234(13) Uani 1 2 d DS TU P . .
H4A H 0.296112 0.153631 0.307461 0.281 Uiso 0.5 1 calc R . . . .
H4B H 0.296112 0.346369 0.307461 0.281 Uiso 0.5 1 calc R . . . .
C3 C 0.323(2) 0.250000 0.1620(16) 0.233(12) Uani 1 2 d DS TU P . .
H3A H 0.376808 0.346784 0.141640 0.279 Uiso 0.5 1 calc R . . . .
H3B H 0.376808 0.153216 0.141640 0.279 Uiso 0.5 1 calc R . . . .
N1 N 0.1453(18) 0.250000 0.1001(13) 0.176(7) Uani 1 2 d DS TU P . .
H1A H 0.118907 0.148220 0.074231 0.211 Uiso 0.5 1 d R . . A -1
H1B H 0.142927 0.317860 0.044141 0.211 Uiso 0.5 1 d R . . A -1
H1C H 0.070857 0.283920 0.134461 0.211 Uiso 0.5 1 d R . . A -1
Fe1 Fe 0.0926(2) 0.250000 0.74248(14) 0.0800(6) Uani 1 2 d S T P . .
I1 I -0.16813(11) 0.250000 0.82591(8) 0.1015(5) Uani 1 2 d S T P B .
I2 I 0.2710(19) 0.0433(18) 0.8864(6) 0.141(3) Uani 0.45(2) 1 d . . . B 1
C6 C 0.586(5) 0.250000 0.4932(18) 0.42(4) Uani 1 2 d DS TU P . .
H6A H 0.642325 0.352430 0.518124 0.632 Uiso 0.5 1 d R . . C -1
H6B H 0.663115 0.159980 0.517394 0.632 Uiso 0.5 1 d R . . C -1
H6C H 0.491605 0.237590 0.523344 0.632 Uiso 0.5 1 d R . . C -1
O2 O -0.0745(19) -0.0158(14) 0.5980(12) 0.196(6) Uani 1 1 d . . . . .
O1 O 0.3715(18) 0.250000 0.6494(14) 0.172(6) Uani 1 2 d S T P . .
I2A I 0.2280(10) -0.0104(13) 0.8672(9) 0.135(2) Uani 0.55(2) 1 d . . . B 2

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
C1 0.104(11) 0.144(15) 0.144(14) 0.000 0.063(10) 0.000
C2 0.121(8) 0.133(10) 0.113(9) -0.008(8) 0.052(7) -0.024(8)
C5 0.21(3) 0.35(5) 0.26(3) 0.000 0.02(2) 0.000
C4 0.24(3) 0.19(3) 0.238(19) 0.000 -0.001(17) 0.000
C3 0.198(17) 0.21(3) 0.25(2) 0.000 0.004(17) 0.000
N1 0.158(13) 0.26(2) 0.113(11) 0.000 0.051(9) 0.000
Fe1 0.0772(11) 0.0913(13) 0.0766(11) 0.000 0.0299(9) 0.000
I1 0.0907(7) 0.1222(9) 0.1024(8) 0.000 0.0447(5) 0.000
I2 0.176(6) 0.150(5) 0.093(2) 0.020(3) 0.035(3) 0.082(4)
C6 0.21(4) 0.76(13) 0.27(3) 0.000 0.02(3) 0.000
O2 0.256(12) 0.181(10) 0.198(11) -0.092(8) 0.142(10) -0.119(9)
O1 0.118(9) 0.242(17) 0.189(14) 0.000 0.096(10) 0.000
I2A 0.124(2) 0.136(4) 0.161(4) 0.048(3) 0.065(2) 0.046(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
C1 Fe1 1.758(18) . ?
C1 O1 1.108(17) . ?
C2 Fe1 1.762(14) . ?
C2 O2 1.139(14) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.5498(10) . ?
C5 C6 1.5499(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.5498(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 N1 1.4500(10) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8898 . ?
Fe1 I1 2.6482(19) . ?
Fe1 I2 2.595(8) . ?
Fe1 I2 2.595(8) 4_565 ?
Fe1 I2A 2.676(7) . ?
Fe1 I2A 2.676(7) 4_565 ?
C6 H6A 0.9600 . ?
C6 H6B 0.9601 . ?
C6 H6C 0.9602 . ?

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
O1 C1 Fe1 175.4(19) . . ?
O2 C2 Fe1 178.8(11) . . ?
H5A C5 H5B 106.4 . . ?
C4 C5 H5A 106.3 . . ?
C4 C5 H5B 106.3 . . ?
C4 C5 C6 124(2) . . ?
C6 C5 H5A 106.3 . . ?
C6 C5 H5B 106.3 . . ?
C5 C4 H4A 107.7 . . ?
C5 C4 H4B 107.7 . . ?
H4A C4 H4B 107.1 . . ?
C3 C4 C5 118.5(16) . . ?
C3 C4 H4A 107.7 . . ?
C3 C4 H4B 107.7 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
N1 C3 C4 113.1(15) . . ?
N1 C3 H3A 109.0 . . ?
N1 C3 H3B 109.0 . . ?
C3 N1 H1A 107.5 . . ?
C3 N1 H1B 102.6 . . ?
C3 N1 H1C 117.9 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 Fe1 C2 93.6(6) . 4_565 ?
C1 Fe1 C2 93.6(6) . . ?
C1 Fe1 I1 179.0(6) . . ?
C1 Fe1 I2 84.4(6) . . ?
C1 Fe1 I2 84.4(6) . 4_565 ?
C1 Fe1 I2A 88.4(4) . 4_565 ?
C1 Fe1 I2A 88.4(4) . . ?
C2 Fe1 C2 96.0(9) . 4_565 ?
C2 Fe1 I1 87.0(4) 4_565 . ?
C2 Fe1 I1 87.0(4) . . ?
C2 Fe1 I2 91.8(6) . . ?
C2 Fe1 I2 172.0(6) 4_565 . ?
C2 Fe1 I2 172.0(6) . 4_565 ?
C2 Fe1 I2 91.8(6) 4_565 4_565 ?
C2 Fe1 I2A 80.0(5) 4_565 4_565 ?
C2 Fe1 I2A 175.6(5) . 4_565 ?
C2 Fe1 I2A 175.6(5) 4_565 . ?
C2 Fe1 I2A 80.0(5) . . ?
I1 Fe1 I2A 90.92(15) . 4_565 ?
I1 Fe1 I2A 90.92(15) . . ?
I2 Fe1 I1 94.8(3) . . ?
I2 Fe1 I1 94.8(3) 4_565 . ?
I2 Fe1 I2 80.3(7) 4_565 . ?
I2 Fe1 I2A 12.3(3) 4_565 4_565 ?
I2 Fe1 I2A 92.2(6) . 4_565 ?
I2A Fe1 I2A 103.9(6) . 4_565 ?
C5 C6 H6A 107.4 . . ?
C5 C6 H6B 106.4 . . ?
C5 C6 H6C 114.6 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
C5 C4 C3 N1 180.000(3) . . . . ?
C6 C5 C4 C3 180.000(5) . . . . ?

_shelx_res_file                  
;
TITL 180624-YXQ-FEIC4NI in P21/m #11
    180624-yxq-feic4ni.res
    created by SHELXL-2018/3 at 21:44:31 on 28-Oct-2019
CELL 0.71073 8.2405 8.0958 12.6129 90 106.571 90
ZERR 2 0.0009 0.0009 0.0012 0 0.001 0
LATT 1
SYMM -X,0.5+Y,-Z
SFAC C H Fe I N O
UNIT 14 24 2 6 2 6
DFIX 1.55 0.001 C6 C5 C4 C3
DFIX 1.55 0.001 C5 C4
DFIX 1.45 0.001 C3 N1
RIGU C6 C5 C4 C3 N1

L.S. 10
PLAN  0
SIZE 0.35 0.07 0.05
TEMP 19.85
BOND $H
CONF
fmap 2
acta
OMIT -3 50
OMIT 0 1 5
OMIT -7 0 3
OMIT 7 0 6
OMIT -3 4 4
OMIT -4 4 6
OMIT -2 1 5
OMIT 1 2 8
OMIT 0 0 6
OMIT 0 1 4
OMIT -1 8 4
OMIT 0 1 2
OMIT -1 1 2
OMIT 1 1 4
OMIT -2 7 3
OMIT 3 1 8
OMIT -5 1 1
REM <olex2.extras>
REM <HklSrc "%.\\180624-YXQ-FEIC4NI.hkl">
REM </olex2.extras>

WGHT    0.084400    0.193900
FVAR       0.39607   0.44623
C1    1    0.268160    0.250000    0.689524    10.50000    0.10444    0.14368 =
         0.14358    0.00000    0.06304    0.00000
C2    1   -0.009931    0.088268    0.655435    11.00000    0.12129    0.13287 =
         0.11327   -0.00770    0.05243   -0.02362
C5    1    0.537085    0.250000    0.365064    10.50000    0.21110    0.35042 =
         0.25811    0.00000    0.02428    0.00000
AFIX  23
H5A   2    0.591552    0.345948    0.344257    10.50000   -1.20000
H5B   2    0.591552    0.154052    0.344257    10.50000   -1.20000
AFIX   0
C4    1    0.352506    0.250000    0.288966    10.50000    0.23546    0.18535 =
         0.23791    0.00000   -0.00128    0.00000
AFIX  23
H4A   2    0.296112    0.153631    0.307461    10.50000   -1.20000
H4B   2    0.296112    0.346369    0.307461    10.50000   -1.20000
AFIX   0
C3    1    0.323060    0.250000    0.161996    10.50000    0.19789    0.21264 =
         0.25041    0.00000    0.00408    0.00000
AFIX  23
H3A   2    0.376808    0.346784    0.141640    10.50000   -1.20000
H3B   2    0.376808    0.153216    0.141640    10.50000   -1.20000
AFIX   0
N1    5    0.145327    0.250000    0.100081    10.50000    0.15781    0.26418 =
         0.11259    0.00000    0.05098    0.00000
PART -1
AFIX   3
H1A   2    0.118907    0.148220    0.074231    10.50000   -1.20000
H1B   2    0.142927    0.317860    0.044141    10.50000   -1.20000
H1C   2    0.070857    0.283920    0.134461    10.50000   -1.20000
AFIX   0
PART 0
FE1   3    0.092596    0.250000    0.742475    10.50000    0.07717    0.09130 =
         0.07655    0.00000    0.02991    0.00000
I1    4   -0.168130    0.250000    0.825906    10.50000    0.09068    0.12219 =
         0.10239    0.00000    0.04467    0.00000
PART 1
I2    4    0.271029    0.043337    0.886424    21.00000    0.17613    0.15002 =
         0.09319    0.01999    0.03478    0.08201
PART 0
C6    1    0.585535    0.250000    0.493174    10.50000    0.20542    0.75772 =
         0.27079    0.00000    0.01975    0.00000
PART -1
AFIX   3
H6A   2    0.642325    0.352430    0.518124    10.50000   -1.50000
H6B   2    0.663115    0.159980    0.517394    10.50000   -1.50000
H6C   2    0.491605    0.237590    0.523344    10.50000   -1.50000
AFIX   0
PART 0
O2    6   -0.074454   -0.015759    0.597984    11.00000    0.25614    0.18129 =
         0.19834   -0.09237    0.14181   -0.11920
O1    6    0.371517    0.250000    0.649422    10.50000    0.11835    0.24175 =
         0.18867    0.00000    0.09646    0.00000
PART 2
I2A   4    0.228008   -0.010360    0.867178   -21.00000    0.12437    0.13601 =
         0.16067    0.04839    0.06494    0.04628
HKLF 4




REM  180624-YXQ-FEIC4NI in P21/m #11
REM wR2 = 0.1711, GooF = S = 1.040, Restrained GooF = 1.037 for all data
REM R1 = 0.0572 for 935 Fo > 4sig(Fo) and 0.0890 for all 1515 data
REM 92 parameters refined using 25 restraints

END

WGHT      0.0844      0.1939

REM Highest difference peak  1.080,  deepest hole -0.520,  1-sigma level  0.131
Q1    1   0.2061  0.2500  0.2011  10.50000  0.05    1.08
Q2    1  -0.0286  0.2500  0.8821  10.50000  0.05    0.65
Q3    1   0.3581  0.2500  0.1989  10.50000  0.05    0.63
Q4    1  -0.0557  0.2500  0.7858  10.50000  0.05    0.59
Q5    1   0.4347  0.2500  0.6313  10.50000  0.05    0.50
Q6    1  -0.1943  0.2500  0.7369  10.50000  0.05    0.50
Q7    1   0.6813  0.2500  0.4156  10.50000  0.05    0.47
Q8    1   0.3179 -0.0034  0.8201  11.00000  0.05    0.46
Q9    1  -0.0913  0.1569  0.8623  11.00000  0.05    0.44
Q10   1   0.2845 -0.0128  0.8006  11.00000  0.05    0.44
Q11   1   0.4934  0.1969  0.3457  11.00000  0.05    0.43
Q12   1   0.2497  0.0250  0.9737  11.00000  0.05    0.42
Q13   1  -0.0352  0.2500  0.7296  10.50000  0.05    0.42
Q14   1   0.2225  0.0493  0.9579  11.00000  0.05    0.40
Q15   1  -0.3311  0.2500  0.7817  10.50000  0.05    0.40
Q16   1   0.1428  0.2500  0.6587  10.50000  0.05    0.39
Q17   1  -0.1949  0.2500  0.9013  10.50000  0.05    0.38
Q18   1  -0.1062 -0.0168  0.6100  11.00000  0.05    0.35
Q19   1   0.0298  0.0020  0.5995  11.00000  0.05    0.35
Q20   1   0.0991  0.0057  0.8519  11.00000  0.05    0.35
;
_shelx_res_checksum              81498
_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 1.378
_oxdiff_exptl_absorpt_empirical_full_min 0.695
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/hexane'
_chemical_properties_physical    
Air-sensitive,Heat-sensitive,Light-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_180624-yxq-fec5ni_tw
_database_code_depnum_ccdc_archive 'CCDC 1963449'
loop_
_audit_author_name
_audit_author_address
'Zhiyin Xiao'
;Jiaxing University
China
;
_audit_update_record             
;
2019-11-02 deposited with the CCDC.	2020-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-10-28
_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        'salt 4'
_chemical_formula_moiety         'C3 Fe I3 O3, C5 H14 N'
_chemical_formula_sum            'C8 H14 Fe I3 N O3'
_chemical_formula_weight         608.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'H C N O Fe I'
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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.092(2)
_cell_length_b                   8.2197(8)
_cell_length_c                   13.3496(16)
_cell_angle_alpha                100.214(9)
_cell_angle_beta                 94.639(16)
_cell_angle_gamma                92.457(16)
_cell_volume                     869.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1582
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.7780
_cell_measurement_theta_min      3.5000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            dark-red
_exptl_crystal_colour_primary    dark-red
_exptl_crystal_density_diffrn    2.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3010
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.849
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  23.00   1.00    6.00    --  -15.89 -99.00-150.00   26
  2  ω     -9.00  23.00   1.00    6.00    --  -15.89 -99.00  60.00   32
  3  ω     16.00  72.00   1.00    6.00    --   16.05  38.00  30.00   56
  4  ω     35.00  60.00   1.00    6.00    --   16.05 178.00-150.00   25
  5  ω      0.00  84.00   1.00    6.00    --   16.05  38.00  90.00   84
  6  ω     20.00  89.00   1.00    6.00    --   16.05-159.00 -89.00   69
  7  ω    -53.00  25.00   1.00    6.00    --   16.05 -38.00 -90.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0075689000
_diffrn_orient_matrix_UB_12      -0.0779599000
_diffrn_orient_matrix_UB_13      0.0152097000
_diffrn_orient_matrix_UB_21      0.0069549000
_diffrn_orient_matrix_UB_22      -0.0376152000
_diffrn_orient_matrix_UB_23      -0.0514599000
_diffrn_orient_matrix_UB_31      0.0874935000
_diffrn_orient_matrix_UB_32      0.0148929000
_diffrn_orient_matrix_UB_33      0.0076864000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1765
_reflns_number_total             3010
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    ?
_refine_diff_density_max         2.715
_refine_diff_density_min         -1.404
_refine_diff_density_rms         0.362
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         3010
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.1625
_refine_ls_R_factor_gt           0.1170
_refine_ls_restrained_S_all      1.041
_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)+(0.1780P)²+7.1201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2920
_refine_ls_wR_factor_ref         0.3462
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.634(9)
 0.366(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H,H) groups
3. Restrained distances
 C8-C7 = C6-C5
 1.5 with sigma of 0.001
 C4-C5 = C6-C7
 1.5 with sigma of 0.001
 C4-N1
 1.4 with sigma of 0.001
4. Rigid body (RIGU) restrains
 N1, C4, C5, C6, C7, C8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
5.b Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_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
I1 I 0.9824(3) 0.2715(3) 0.88642(16) 0.1019(8) Uani 1 1 d . . . . .
I2 I 0.5024(2) 0.2324(3) 0.87001(17) 0.1011(8) Uani 1 1 d . . . . .
I3 I 0.7522(2) -0.1565(2) 0.83378(15) 0.0882(7) Uani 1 1 d . . . . .
Fe1 Fe 0.7394(4) 0.1176(4) 0.7543(3) 0.0717(10) Uani 1 1 d . . . . .
O1 O 0.727(3) 0.415(3) 0.671(2) 0.131(8) Uani 1 1 d . . . . .
O2 O 1.003(3) 0.003(3) 0.629(2) 0.131(9) Uani 1 1 d . . . . .
O3 O 0.468(3) -0.043(3) 0.6101(18) 0.120(8) Uani 1 1 d . . . . .
C1 C 0.729(4) 0.305(3) 0.705(2) 0.084(7) Uani 1 1 d . . . . .
C2 C 0.909(4) 0.044(4) 0.677(2) 0.092(8) Uani 1 1 d . . . . .
C3 C 0.587(4) 0.014(5) 0.668(3) 0.112(11) Uani 1 1 d . . . . .
N1 N 0.771(4) 0.143(2) 0.090(2) 0.127(10) Uani 1 1 d D U . . .
H1A H 0.874590 0.147092 0.072282 0.190 Uiso 1 1 calc GR . . . .
H1B H 0.700629 0.120218 0.033600 0.190 Uiso 1 1 calc GR . . . .
H1C H 0.758535 0.063954 0.126872 0.190 Uiso 1 1 calc GR . . . .
C4 C 0.738(4) 0.296(3) 0.1472(14) 0.136(12) Uani 1 1 d D U . . .
H4A H 0.619078 0.309632 0.139555 0.164 Uiso 1 1 calc R . . . .
H4B H 0.792999 0.383500 0.120283 0.164 Uiso 1 1 calc R . . . .
C5 C 0.793(4) 0.312(3) 0.2586(14) 0.138(12) Uani 1 1 d D U . . .
H5A H 0.743366 0.221362 0.285384 0.166 Uiso 1 1 calc R . . . .
H5B H 0.912987 0.307105 0.267457 0.166 Uiso 1 1 calc R . . . .
C6 C 0.744(6) 0.474(3) 0.3164(15) 0.18(2) Uani 1 1 d D U . . .
H6A H 0.625616 0.482905 0.300734 0.219 Uiso 1 1 calc R . . . .
H6B H 0.802022 0.563619 0.293155 0.219 Uiso 1 1 calc R . . . .
C7 C 0.780(7) 0.493(4) 0.4300(15) 0.20(2) Uani 1 1 d D U . . .
H7A H 0.711211 0.412038 0.455414 0.237 Uiso 1 1 calc R . . . .
H7B H 0.895158 0.473064 0.446304 0.237 Uiso 1 1 calc R . . . .
C8 C 0.744(8) 0.664(4) 0.481(4) 0.24(3) Uani 1 1 d D U . . .
H8A H 0.783818 0.681453 0.551543 0.355 Uiso 1 1 calc GR . . . .
H8B H 0.626553 0.676866 0.474152 0.355 Uiso 1 1 calc GR . . . .
H8C H 0.799271 0.743910 0.448160 0.355 Uiso 1 1 calc GR . . . .

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
I1 0.1015(14) 0.1052(16) 0.0998(15) 0.0298(11) 0.0060(10) -0.0271(11)
I2 0.1019(14) 0.1065(16) 0.1115(16) 0.0460(13) 0.0364(11) 0.0348(11)
I3 0.1078(14) 0.0675(11) 0.0969(14) 0.0342(9) 0.0131(9) 0.0049(9)
Fe1 0.084(2) 0.067(2) 0.072(2) 0.0299(17) 0.0155(16) 0.0062(17)
O1 0.14(2) 0.099(17) 0.17(2) 0.077(17) 0.023(16) 0.010(14)
O2 0.140(18) 0.14(2) 0.130(19) 0.046(16) 0.082(16) 0.044(16)
O3 0.129(18) 0.14(2) 0.105(16) 0.064(15) -0.001(13) -0.003(15)
C1 0.13(2) 0.060(15) 0.082(17) 0.033(13) 0.047(15) 0.028(14)
C2 0.11(2) 0.073(18) 0.10(2) 0.031(16) 0.015(16) 0.021(15)
C3 0.088(19) 0.12(3) 0.15(3) 0.08(2) -0.002(19) -0.020(18)
N1 0.16(2) 0.082(13) 0.141(19) 0.028(13) 0.028(17) -0.041(16)
C4 0.22(4) 0.082(14) 0.128(16) 0.066(13) 0.06(2) 0.00(2)
C5 0.20(4) 0.10(2) 0.129(16) 0.049(15) 0.06(2) 0.01(2)
C6 0.33(6) 0.13(3) 0.120(17) 0.075(16) 0.07(3) 0.10(4)
C7 0.31(7) 0.16(4) 0.119(18) 0.03(2) 0.02(3) 0.00(5)
C8 0.32(8) 0.18(4) 0.19(4) -0.02(3) 0.03(5) -0.02(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
I1 Fe1 2.648(4) . ?
I2 Fe1 2.659(4) . ?
I3 Fe1 2.657(4) . ?
Fe1 C1 1.78(2) . ?
Fe1 C2 1.84(3) . ?
Fe1 C3 1.71(4) . ?
O1 C1 1.08(3) . ?
O2 C2 1.07(3) . ?
O3 C3 1.20(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C4 1.4000(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.4999(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.5000(10) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.5000(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.5000(11) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
I1 Fe1 I2 93.61(13) . . ?
I1 Fe1 I3 92.50(12) . . ?
I3 Fe1 I2 92.32(11) . . ?
C1 Fe1 I1 86.5(10) . . ?
C1 Fe1 I2 86.0(8) . . ?
C1 Fe1 I3 178.0(8) . . ?
C1 Fe1 C2 93.3(12) . . ?
C2 Fe1 I1 84.2(10) . . ?
C2 Fe1 I2 177.7(10) . . ?
C2 Fe1 I3 88.4(9) . . ?
C3 Fe1 I1 178.1(14) . . ?
C3 Fe1 I2 88.1(13) . . ?
C3 Fe1 I3 86.7(10) . . ?
C3 Fe1 C1 94.4(14) . . ?
C3 Fe1 C2 94.1(17) . . ?
O1 C1 Fe1 176(3) . . ?
O2 C2 Fe1 177(3) . . ?
O3 C3 Fe1 172(4) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C4 N1 H1A 109.5 . . ?
C4 N1 H1B 109.5 . . ?
C4 N1 H1C 109.5 . . ?
N1 C4 H4A 109.0 . . ?
N1 C4 H4B 109.0 . . ?
N1 C4 C5 113(2) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C4 110.2(18) . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
C5 C6 C7 114(2) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C6 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 C6 110(3) . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
N1 C4 C5 C6 -176(3) . . . . ?
C4 C5 C6 C7 174(3) . . . . ?
C5 C6 C7 C8 174(4) . . . . ?

_shelx_res_file                  
;
TITL 180624-yxq-fec5ni_a.res in P-1
    180624-yxq-fec5ni_tw.res
    created by SHELXL-2018/3 at 22:06:25 on 28-Oct-2019
CELL 0.71073 8.0918 8.2197 13.3496 100.214 94.639 92.457
ZERR 2 0.002 0.0008 0.0016 0.009 0.016 0.016
LATT 1
SFAC C H Fe I N O
UNIT 16 28 2 6 2 6
DFIX 1.5 0.001 C8 C7 C6 C5
DFIX 1.5 0.001 C4 C5 C6 C7
DFIX 1.4 0.001 C4 N1
RIGU N1 > C8

L.S. 10
PLAN  20
TEMP 24.85
BOND $H
LIST 4
conf
fmap 2
acta
OMIT -3 3 7
OMIT 2 2 8
OMIT -1 5 2
OMIT -4 1 0
OMIT -1 0 8
OMIT 2 5 5
OMIT -2 2 8
OMIT 0 -3 2
OMIT -5 1 7
OMIT 0 -1 2
OMIT -2 5 5
OMIT 3 -3 4
OMIT 8 0 1
OMIT 4 0 1
OMIT -1 -5 4
OMIT -1 1 7
OMIT 2 3 5
OMIT 0 4 6
OMIT -1 5 5
OMIT 4 -4 5
OMIT -5 0 8
OMIT 0 -2 1
OMIT 0 -3 5
OMIT 0 4 3
OMIT 0 -6 5
OMIT 0 2 9
REM <olex2.extras>
REM <HklSrc "%.\\180624-YXQ-FEC5NI_tw.hkl">
REM </olex2.extras>

WGHT    0.178000    7.120100
BASF   0.36599
FVAR       3.85232
I1    4    0.982436    0.271495    0.886415    11.00000    0.10147    0.10521 =
         0.09979    0.02982    0.00599   -0.02714
I2    4    0.502415    0.232448    0.870014    11.00000    0.10188    0.10654 =
         0.11152    0.04603    0.03636    0.03476
I3    4    0.752235   -0.156474    0.833776    11.00000    0.10780    0.06754 =
         0.09685    0.03425    0.01306    0.00488
FE1   3    0.739382    0.117630    0.754312    11.00000    0.08438    0.06721 =
         0.07152    0.02988    0.01545    0.00617
O1    6    0.726513    0.415096    0.671097    11.00000    0.14072    0.09948 =
         0.17278    0.07689    0.02260    0.00961
O2    6    1.003167    0.002664    0.628639    11.00000    0.13967    0.14488 =
         0.13011    0.04622    0.08181    0.04436
O3    6    0.468204   -0.043152    0.610087    11.00000    0.12932    0.13894 =
         0.10485    0.06406   -0.00050   -0.00314
C1    1    0.728904    0.305015    0.705322    11.00000    0.12555    0.05987 =
         0.08202    0.03325    0.04695    0.02839
C2    1    0.909373    0.044269    0.677292    11.00000    0.10809    0.07291 =
         0.10338    0.03135    0.01545    0.02074
C3    1    0.587126    0.013739    0.667529    11.00000    0.08804    0.11891 =
         0.14623    0.07994   -0.00246   -0.02009
N1    5    0.770867    0.142818    0.089752    11.00000    0.15806    0.08203 =
         0.14113    0.02841    0.02813   -0.04088
AFIX 137
H1A   2    0.874590    0.147092    0.072282    11.00000   -1.50000
H1B   2    0.700629    0.120218    0.033600    11.00000   -1.50000
H1C   2    0.758535    0.063954    0.126872    11.00000   -1.50000
AFIX   0
C4    1    0.737592    0.295697    0.147171    11.00000    0.22288    0.08206 =
         0.12835    0.06650    0.05887    0.00217
AFIX  23
H4A   2    0.619078    0.309632    0.139555    11.00000   -1.20000
H4B   2    0.792999    0.383500    0.120283    11.00000   -1.20000
AFIX   0
C5    1    0.793272    0.312251    0.258627    11.00000    0.19955    0.10302 =
         0.12936    0.04912    0.05629    0.01404
AFIX  23
H5A   2    0.743366    0.221362    0.285384    11.00000   -1.20000
H5B   2    0.912987    0.307105    0.267457    11.00000   -1.20000
AFIX   0
C6    1    0.743632    0.473697    0.316395    11.00000    0.33037    0.13314 =
         0.11962    0.07541    0.06718    0.09751
AFIX  23
H6A   2    0.625616    0.482905    0.300734    11.00000   -1.20000
H6B   2    0.802022    0.563619    0.293155    11.00000   -1.20000
AFIX   0
C7    1    0.779589    0.492833    0.430011    11.00000    0.31217    0.16325 =
         0.11863    0.02992    0.02456   -0.00107
AFIX  23
H7A   2    0.711211    0.412038    0.455414    11.00000   -1.20000
H7B   2    0.895158    0.473064    0.446304    11.00000   -1.20000
AFIX   0
C8    1    0.744115    0.664187    0.480511    11.00000    0.31694    0.17528 =
         0.19375   -0.02461    0.02623   -0.02336
AFIX 137
H8A   2    0.783818    0.681453    0.551543    11.00000   -1.50000
H8B   2    0.626553    0.676866    0.474152    11.00000   -1.50000
H8C   2    0.799271    0.743910    0.448160    11.00000   -1.50000
AFIX   0
HKLF 5




REM  180624-yxq-fec5ni_a.res in P-1
REM wR2 = 0.3462, GooF = S = 1.046, Restrained GooF = 1.041 for all data
REM R1 = 0.1170 for 1765 Fo > 4sig(Fo) and 0.1625 for all 3010 data
REM 148 parameters refined using 32 restraints

END

WGHT      0.1782      7.0839

REM Highest difference peak  2.715,  deepest hole -1.404,  1-sigma level  0.362
Q1    1   0.9975  0.1847  0.8142  11.00000  0.05    2.71
Q2    1   0.7476 -0.0782  0.9083  11.00000  0.05    2.54
Q3    1   0.7400 -0.2505  0.7439  11.00000  0.05    2.37
Q4    1   1.0055  0.3457  0.9595  11.00000  0.05    2.18
Q5    1   0.5169  0.3200  0.9432  11.00000  0.05    2.14
Q6    1   0.8897 -0.1417  0.8412  11.00000  0.05    1.74
Q7    1   0.6247 -0.1578  0.8341  11.00000  0.05    1.72
Q8    1   0.5243  0.1555  0.7894  11.00000  0.05    1.59
Q9    1   0.8354  0.2555  0.8660  11.00000  0.05    1.46
Q10   1   1.1149  0.2759  0.8870  11.00000  0.05    1.44
Q11   1   0.6796  0.2217  0.8629  11.00000  0.05    1.40
Q12   1   0.7420  0.1991  0.8413  11.00000  0.05    1.31
Q13   1   0.3595  0.2432  0.8732  11.00000  0.05    1.23
Q14   1   0.7499  0.5945  0.3532  11.00000  0.05    1.22
Q15   1   0.7371  0.2760  0.5842  11.00000  0.05    1.14
Q16   1   0.7548  0.1030  0.1197  11.00000  0.05    1.00
Q17   1   0.7350  0.6958  0.4563  11.00000  0.05    0.96
Q18   1   0.7441  0.0094  0.6573  11.00000  0.05    0.89
Q19   1   0.7418  0.2124  0.2026  11.00000  0.05    0.88
Q20   1   0.8864  0.2760  0.6437  11.00000  0.05    0.83
;
_shelx_res_checksum              1443
_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 1.803
_oxdiff_exptl_absorpt_empirical_full_min 0.576
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.634(9)
2 0.366(9)

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/hexane'
_chemical_properties_physical    
Air-sensitive,Heat-sensitive,Light-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_180611-yxq-feprico
_database_code_depnum_ccdc_archive 'CCDC 1963447'
loop_
_audit_author_name
_audit_author_address
'Zhiyin Xiao'
;Jiaxing University
China
;
_audit_update_record             
;
2019-11-02 deposited with the CCDC.	2020-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-10-28
_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        'salt 2'
_chemical_formula_moiety         'C3 Fe I3 O3, C3 H10 N'
_chemical_formula_sum            'C6 H10 Fe I3 N O3'
_chemical_formula_weight         580.70
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Fe I'
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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.0358(10)
_cell_length_b                   7.9704(3)
_cell_length_c                   16.4638(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.505(8)
_cell_angle_gamma                90
_cell_volume                     1497.71(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2747
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.5860
_cell_measurement_theta_min      3.1300
_shelx_estimated_absorpt_T_max   0.506
_shelx_estimated_absorpt_T_min   0.071
_exptl_absorpt_coefficient_mu    7.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    2.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12199
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.317
_diffrn_reflns_theta_min         2.869
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00 -35.00   1.00    2.90    --  -15.74 140.00 -70.00   42
  2  ω    -21.00  23.00   1.00    2.90    --  -15.74 -99.00-180.00   44
  3  ω    -71.00 -31.00   1.00    2.90    --  -15.74 130.00 115.00   40
  4  ω      8.00  70.00   1.00    2.90    --   16.05  57.00 -60.00   62
  5  ω    -31.00  32.00   1.00    2.90    --   16.05 -57.00  60.00   63
  6  ω    -48.00  85.00   1.00    2.90    --   16.05   0.00 -90.00  133
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0611963000
_diffrn_orient_matrix_UB_12      -0.0090074000
_diffrn_orient_matrix_UB_13      -0.0082606000
_diffrn_orient_matrix_UB_21      -0.0085144000
_diffrn_orient_matrix_UB_22      -0.0015046000
_diffrn_orient_matrix_UB_23      -0.0446615000
_diffrn_orient_matrix_UB_31      0.0063936000
_diffrn_orient_matrix_UB_32      -0.0885340000
_diffrn_orient_matrix_UB_33      0.0016117000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2166
_reflns_number_total             3575
_reflns_odcompleteness_completeness 99.76
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         1.393
_refine_diff_density_min         -1.429
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0596
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0179P)²+13.3054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1177
_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, All N(H,H,H) groups
2. Restrained distances
 C5-C4
 1.5 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C4, C5, N1, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
4.b Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_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
C1 C 0.6702(9) 0.7618(14) 0.6300(7) 0.077(3) Uani 1 1 d . . . . .
C2 C 0.6239(10) 0.8703(15) 0.4740(7) 0.079(3) Uani 1 1 d . . . . .
C3 C 0.6577(11) 0.5446(16) 0.5069(8) 0.089(3) Uani 1 1 d . . . . .
C4 C 0.3141(13) 0.720(3) 0.1912(11) 0.161(7) Uani 1 1 d D U . . .
H4A H 0.332194 0.639684 0.153085 0.193 Uiso 1 1 calc R . . . .
H4B H 0.335138 0.829726 0.174673 0.193 Uiso 1 1 calc R . . . .
C5 C 0.1911(13) 0.720(2) 0.1709(10) 0.132(5) Uani 1 1 d D U . . .
H5A H 0.171260 0.620135 0.196752 0.159 Uiso 1 1 calc R . . . .
H5B H 0.171864 0.814907 0.201108 0.159 Uiso 1 1 calc R . . . .
N1 N 0.1141(10) 0.7269(18) 0.0880(8) 0.149(5) Uani 1 1 d . U . . .
H1A H 0.154518 0.731510 0.051179 0.223 Uiso 1 1 calc GR . . . .
H1B H 0.069207 0.817751 0.081900 0.223 Uiso 1 1 calc GR . . . .
H1C H 0.069201 0.635619 0.077638 0.223 Uiso 1 1 calc GR . . . .
Fe1 Fe 0.73118(12) 0.74026(16) 0.54454(9) 0.0594(3) Uani 1 1 d . . . . .
I1 I 0.84425(8) 1.02259(10) 0.60155(5) 0.0968(3) Uani 1 1 d . . . . .
I2 I 0.89294(8) 0.55028(12) 0.65083(7) 0.1155(4) Uani 1 1 d . . . . .
I3 I 0.82726(8) 0.71491(11) 0.42029(5) 0.0909(3) Uani 1 1 d . . . . .
C6 C 0.3891(14) 0.689(3) 0.2700(10) 0.172(8) Uani 1 1 d . U . . .
H6A H 0.397974 0.570178 0.278551 0.258 Uiso 1 1 calc GR . . . .
H6B H 0.358879 0.736740 0.312260 0.258 Uiso 1 1 calc GR . . . .
H6C H 0.463850 0.738425 0.275213 0.258 Uiso 1 1 calc GR . . . .
O1 O 0.6293(8) 0.7731(12) 0.6817(5) 0.112(3) Uani 1 1 d . . . . .
O2 O 0.5532(8) 0.9517(13) 0.4288(6) 0.115(3) Uani 1 1 d . . . . .
O3 O 0.6142(8) 0.4273(11) 0.4833(6) 0.113(3) 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
C1 0.065(7) 0.095(8) 0.072(7) 0.011(6) 0.021(6) 0.005(6)
C2 0.064(7) 0.106(9) 0.069(7) -0.003(6) 0.024(6) 0.009(6)
C3 0.077(8) 0.093(9) 0.110(9) -0.019(7) 0.047(7) -0.009(7)
C4 0.105(9) 0.23(2) 0.138(12) 0.013(14) 0.021(9) 0.023(13)
C5 0.108(9) 0.155(14) 0.126(10) 0.025(11) 0.027(8) 0.039(11)
N1 0.092(9) 0.205(14) 0.134(9) -0.066(10) 0.013(7) 0.015(9)
Fe1 0.0505(8) 0.0615(8) 0.0685(8) -0.0025(6) 0.0221(7) -0.0002(6)
I1 0.1188(7) 0.0818(5) 0.0878(5) -0.0206(4) 0.0299(5) -0.0293(5)
I2 0.0727(6) 0.1194(7) 0.1597(9) 0.0727(6) 0.0446(6) 0.0201(5)
I3 0.0949(6) 0.0972(6) 0.0983(6) -0.0151(4) 0.0559(5) -0.0064(5)
C6 0.112(12) 0.27(2) 0.127(12) 0.036(15) 0.026(9) 0.010(15)
O1 0.118(7) 0.151(8) 0.087(6) 0.018(6) 0.059(6) 0.018(6)
O2 0.085(6) 0.151(8) 0.100(6) 0.031(6) 0.017(5) 0.036(6)
O3 0.101(7) 0.088(6) 0.166(9) -0.050(6) 0.065(6) -0.037(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
C1 Fe1 1.790(12) . ?
C1 O1 1.113(12) . ?
C2 Fe1 1.772(12) . ?
C2 O2 1.139(12) . ?
C3 Fe1 1.802(13) . ?
C3 O3 1.082(12) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.411(14) . ?
C4 C6 1.347(18) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 N1 1.387(16) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
Fe1 I1 2.6431(15) . ?
Fe1 I2 2.6425(16) . ?
Fe1 I3 2.6580(15) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

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
O1 C1 Fe1 178.0(11) . . ?
O2 C2 Fe1 178.6(11) . . ?
O3 C3 Fe1 178.9(12) . . ?
H4A C4 H4B 106.4 . . ?
C5 C4 H4A 106.3 . . ?
C5 C4 H4B 106.3 . . ?
C6 C4 H4A 106.3 . . ?
C6 C4 H4B 106.3 . . ?
C6 C4 C5 124.0(17) . . ?
C4 C5 H5A 106.4 . . ?
C4 C5 H5B 106.4 . . ?
H5A C5 H5B 106.5 . . ?
N1 C5 C4 123.8(15) . . ?
N1 C5 H5A 106.4 . . ?
N1 C5 H5B 106.4 . . ?
C5 N1 H1A 109.5 . . ?
C5 N1 H1B 109.5 . . ?
C5 N1 H1C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 Fe1 C3 94.3(5) . . ?
C1 Fe1 I1 86.1(4) . . ?
C1 Fe1 I2 86.2(3) . . ?
C1 Fe1 I3 178.2(4) . . ?
C2 Fe1 C1 93.7(5) . . ?
C2 Fe1 C3 96.0(6) . . ?
C2 Fe1 I1 85.4(4) . . ?
C2 Fe1 I2 179.2(4) . . ?
C2 Fe1 I3 86.8(3) . . ?
C3 Fe1 I1 178.4(4) . . ?
C3 Fe1 I2 84.8(4) . . ?
C3 Fe1 I3 87.5(4) . . ?
I1 Fe1 I3 92.14(5) . . ?
I2 Fe1 I1 93.70(5) . . ?
I2 Fe1 I3 93.27(5) . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
C6 C4 C5 N1 -170(2) . . . . ?

_shelx_res_file                  
;
TITL 180611-yxq-feprico_a.res in P2(1)/c
    180611-yxq-feprico.res
    created by SHELXL-2018/3 at 21:17:40 on 28-Oct-2019
CELL 0.71073 12.0358 7.9704 16.4638 90 108.505 90
ZERR 4 0.001 0.0003 0.001 0 0.008 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Fe I N O
UNIT 24 40 4 12 4 12
DFIX 1.5 C5 C4
RIGU C4 C5 N1 C6

L.S. 4
PLAN  5
SIZE 0.78 0.26 0.11
BOND $h
conf
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\180611-YXQ-FePrICO.hkl">
REM </olex2.extras>

WGHT    0.017900   13.305400
FVAR       0.20875
C1    1    0.670165    0.761831    0.630019    11.00000    0.06498    0.09485 =
         0.07192    0.01059    0.02145    0.00468
C2    1    0.623922    0.870318    0.473962    11.00000    0.06450    0.10607 =
         0.06885   -0.00286    0.02391    0.00916
C3    1    0.657739    0.544644    0.506944    11.00000    0.07743    0.09261 =
         0.10977   -0.01895    0.04702   -0.00930
C4    1    0.314131    0.720385    0.191179    11.00000    0.10503    0.22649 =
         0.13829    0.01271    0.02142    0.02324
AFIX  23
H4A   2    0.332194    0.639684    0.153085    11.00000   -1.20000
H4B   2    0.335138    0.829726    0.174673    11.00000   -1.20000
AFIX   0
C5    1    0.191087    0.720402    0.170921    11.00000    0.10811    0.15495 =
         0.12589    0.02464    0.02650    0.03946
AFIX  23
H5A   2    0.171260    0.620135    0.196752    11.00000   -1.20000
H5B   2    0.171864    0.814907    0.201108    11.00000   -1.20000
AFIX   0
N1    5    0.114112    0.726902    0.087984    11.00000    0.09164    0.20460 =
         0.13418   -0.06647    0.01293    0.01488
AFIX 137
H1A   2    0.154518    0.731510    0.051179    11.00000   -1.50000
H1B   2    0.069207    0.817751    0.081900    11.00000   -1.50000
H1C   2    0.069201    0.635619    0.077638    11.00000   -1.50000
AFIX   0

FE1   3    0.731182    0.740261    0.544540    11.00000    0.05047    0.06153 =
         0.06854   -0.00253    0.02211   -0.00020
I1    4    0.844253    1.022594    0.601550    11.00000    0.11882    0.08183 =
         0.08781   -0.02061    0.02992   -0.02928
I2    4    0.892938    0.550284    0.650830    11.00000    0.07269    0.11943 =
         0.15971    0.07275    0.04456    0.02011
I3    4    0.827264    0.714908    0.420286    11.00000    0.09491    0.09722 =
         0.09829   -0.01505    0.05590   -0.00642
C6    1    0.389097    0.689190    0.269964    11.00000    0.11178    0.26856 =
         0.12744    0.03642    0.02586    0.00974
AFIX 137
H6A   2    0.397974    0.570178    0.278551    11.00000   -1.50000
H6B   2    0.358879    0.736740    0.312260    11.00000   -1.50000
H6C   2    0.463850    0.738425    0.275213    11.00000   -1.50000
AFIX   0

O1    6    0.629292    0.773106    0.681702    11.00000    0.11805    0.15147 =
         0.08665    0.01816    0.05927    0.01801
O2    6    0.553233    0.951718    0.428756    11.00000    0.08482    0.15081 =
         0.09996    0.03088    0.01656    0.03590
O3    6    0.614245    0.427332    0.483341    11.00000    0.10148    0.08777 =
         0.16603   -0.04975    0.06548   -0.03733
HKLF 4




REM  180611-yxq-feprico_a.res in P2(1)/c
REM wR2 = 0.1177, GooF = S = 1.032, Restrained GooF = 1.033 for all data
REM R1 = 0.0596 for 2166 Fo > 4sig(Fo) and 0.1065 for all 3575 data
REM 129 parameters refined using 16 restraints

END

WGHT      0.0180     13.2663

REM Highest difference peak  1.393,  deepest hole -1.429,  1-sigma level  0.134
Q1    1   0.8957  0.6491  0.6814  11.00000  0.05    1.39
Q2    1   0.8754  0.9453  0.6436  11.00000  0.05    1.17
Q3    1   0.8428  0.5149  0.6013  11.00000  0.05    0.91
Q4    1   0.8928  0.7108  0.4727  11.00000  0.05    0.89
Q5    1   0.9084  0.5110  0.6520  11.00000  0.05    0.89
;
_shelx_res_checksum              65604
_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 2.835
_oxdiff_exptl_absorpt_empirical_full_min 0.523
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/hexane'
_chemical_properties_physical    
Air-sensitive,Heat-sensitive,Light-sensitive,Photo-sensitive
