# 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 2017

####################################################################### 
# 
# 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_evg033_3_new
_database_code_depnum_ccdc_archive 'CCDC 942440'
_audit_update_record             
;
2013-06-02 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H16 Br2 Cl3 Fe N4 O'
_chemical_formula_weight         530.29

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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   23.654(6)
_cell_length_b                   8.738(2)
_cell_length_c                   8.595(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1776.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.983
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1036
_exptl_absorpt_coefficient_mu    5.800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5193
_exptl_absorpt_correction_T_max  0.8928
_exptl_absorpt_process_details   SADABS

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18365
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         27.07
_reflns_number_total             1949
_reflns_number_gt                1520
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0379P)²+2.5670P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1949
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.5000 0.77901(7) 0.2500 0.02927(17) Uani 1 2 d S . .
Br1 Br 0.742839(16) 0.79623(5) 0.00210(5) 0.05398(16) Uani 1 1 d . . .
Cl1 Cl 0.44915(4) 0.78245(11) 0.01346(9) 0.0414(2) Uani 1 1 d . . .
Cl2 Cl 0.5000 0.51366(12) 0.2500 0.0357(3) Uani 1 2 d S . .
O1 O 0.5000 1.0154(4) 0.2500 0.0463(9) Uani 1 2 d S . .
H1F H 0.5137 1.0723 0.1792 0.069 Uiso 1 1 d R . .
N1 N 0.57710(11) 0.7809(3) 0.1142(3) 0.0333(6) Uani 1 1 d . . .
N2 N 0.58078(12) 0.6766(3) -0.0030(3) 0.0341(6) Uani 1 1 d . . .
H2 H 0.5523 0.6255 -0.0373 0.041 Uiso 1 1 calc R . .
C1 C 0.64456(15) 0.9602(4) 0.2440(4) 0.0453(8) Uani 1 1 d . . .
H1A H 0.6251 0.9432 0.3405 0.068 Uiso 1 1 calc R . .
H1B H 0.6335 1.0574 0.2017 0.068 Uiso 1 1 calc R . .
H1C H 0.6846 0.9598 0.2621 0.068 Uiso 1 1 calc R . .
C2 C 0.62976(13) 0.8361(4) 0.1317(4) 0.0321(7) Uani 1 1 d . . .
C3 C 0.66508(14) 0.7627(4) 0.0266(4) 0.0331(7) Uani 1 1 d . . .
C4 C 0.63332(13) 0.6618(4) -0.0597(4) 0.0319(7) Uani 1 1 d . . .
C5 C 0.64770(14) 0.5562(4) -0.1900(4) 0.0468(9) Uani 1 1 d . . .
H5A H 0.6344 0.4551 -0.1659 0.070 Uiso 1 1 calc R . .
H5B H 0.6880 0.5541 -0.2041 0.070 Uiso 1 1 calc R . .
H5C H 0.6300 0.5914 -0.2839 0.070 Uiso 1 1 calc R . .

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 0.0298(3) 0.0308(3) 0.0272(3) 0.000 0.0039(3) 0.000
Br1 0.0255(2) 0.0703(3) 0.0662(3) -0.0059(2) 0.00104(17) -0.00753(17)
Cl1 0.0397(5) 0.0532(5) 0.0313(4) 0.0071(4) -0.0008(3) 0.0012(4)
Cl2 0.0358(6) 0.0320(6) 0.0393(6) 0.000 -0.0011(5) 0.000
O1 0.067(2) 0.0320(18) 0.0403(18) 0.000 0.0186(17) 0.000
N1 0.0312(13) 0.0379(15) 0.0307(14) -0.0078(12) 0.0030(11) -0.0060(11)
N2 0.0294(14) 0.0384(15) 0.0345(14) -0.0101(11) 0.0047(11) -0.0075(11)
C1 0.0409(19) 0.049(2) 0.046(2) -0.0098(17) -0.0026(17) -0.0129(16)
C2 0.0327(17) 0.0318(16) 0.0318(16) 0.0033(13) -0.0017(13) -0.0037(13)
C3 0.0257(15) 0.0366(17) 0.0370(17) 0.0022(13) 0.0020(13) -0.0042(13)
C4 0.0302(16) 0.0370(17) 0.0285(15) 0.0023(13) 0.0017(13) -0.0020(13)
C5 0.0353(18) 0.059(2) 0.046(2) -0.0134(18) 0.0104(15) 0.0005(16)

_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 O1 2.066(3) . ?
Fe1 N1 2.165(3) 3_655 ?
Fe1 N1 2.165(3) . ?
Fe1 Cl2 2.3187(13) . ?
Fe1 Cl1 2.3624(9) . ?
Fe1 Cl1 2.3624(9) 3_655 ?
Br1 C3 1.874(3) . ?
N1 C2 1.344(4) . ?
N1 N2 1.361(4) . ?
N2 C4 1.341(4) . ?
C1 C2 1.493(4) . ?
C2 C3 1.388(4) . ?
C3 C4 1.375(5) . ?
C4 C5 1.491(4) . ?

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 Fe1 N1 89.57(7) . 3_655 ?
O1 Fe1 N1 89.57(7) . . ?
N1 Fe1 N1 179.15(15) 3_655 . ?
O1 Fe1 Cl2 180.0 . . ?
N1 Fe1 Cl2 90.43(7) 3_655 . ?
N1 Fe1 Cl2 90.43(7) . . ?
O1 Fe1 Cl1 89.27(3) . . ?
N1 Fe1 Cl1 92.00(7) 3_655 . ?
N1 Fe1 Cl1 87.99(7) . . ?
Cl2 Fe1 Cl1 90.73(3) . . ?
O1 Fe1 Cl1 89.27(3) . 3_655 ?
N1 Fe1 Cl1 87.99(8) 3_655 3_655 ?
N1 Fe1 Cl1 92.00(7) . 3_655 ?
Cl2 Fe1 Cl1 90.73(3) . 3_655 ?
Cl1 Fe1 Cl1 178.54(5) . 3_655 ?
C2 N1 N2 105.3(3) . . ?
C2 N1 Fe1 136.3(2) . . ?
N2 N1 Fe1 116.61(19) . . ?
C4 N2 N1 113.1(3) . . ?
N1 C2 C3 108.6(3) . . ?
N1 C2 C1 123.4(3) . . ?
C3 C2 C1 128.0(3) . . ?
C4 C3 C2 108.6(3) . . ?
C4 C3 Br1 125.2(2) . . ?
C2 C3 Br1 126.3(2) . . ?
N2 C4 C3 104.4(3) . . ?
N2 C4 C5 122.9(3) . . ?
C3 C4 C5 132.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.07
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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_evg028_0m
_database_code_depnum_ccdc_archive 'CCDC 942441'
_audit_update_record             
;
2013-06-02 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H28 Br8 Cl16 Fe2 N8 O'
_chemical_formula_weight         1762.72

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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   I4(1)/a

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   19.167(17)
_cell_length_b                   19.167(17)
_cell_length_c                   16.153(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5934(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.973
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3360
_exptl_absorpt_coefficient_mu    6.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2936
_exptl_absorpt_correction_T_max  0.5162
_exptl_absorpt_process_details   SADABS

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29854
_diffrn_reflns_av_R_equivalents  0.1120
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.26
_reflns_number_total             2977
_reflns_number_gt                1796
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1106P)²+28.3396P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2977
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.2057
_refine_ls_wR_factor_gt          0.1668
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.0000 0.7500 -0.01542(9) 0.0415(4) Uani 1 2 d S . .
Br1 Br -0.11619(5) 0.70806(5) 0.02775(6) 0.0627(4) Uani 1 1 d . . .
Br2 Br 0.11043(7) 0.47618(5) 0.11750(8) 0.0945(5) Uani 1 1 d . . .
Cl1 Cl 0.0776(5) 0.5118(3) 0.3610(4) 0.218(3) Uani 1 1 d . . .
Cl2 Cl 0.1218(8) 0.6466(5) 0.3767(5) 0.358(8) Uani 1 1 d . . .
Cl3 Cl 0.0775(3) 0.5829(4) 0.5174(3) 0.192(2) Uani 1 1 d . . .
Cl4 Cl 0.2005(5) 0.5440(8) 0.4513(6) 0.392(9) Uani 1 1 d . . .
O1 O 0.0000 0.7500 -0.1250 0.045(2) Uani 1 4 d S . .
N1 N 0.0390(4) 0.6479(3) 0.0017(4) 0.0519(16) Uani 1 1 d . . .
N2 N 0.0556(3) 0.6070(3) -0.0636(4) 0.0473(15) Uani 1 1 d . . .
H2 H 0.0502 0.6187 -0.1146 0.057 Uiso 1 1 calc R . .
C1 C 0.0462(6) 0.6422(5) 0.1545(6) 0.082(3) Uani 1 1 d . . .
H1A H 0.0043 0.6696 0.1557 0.124 Uiso 1 1 calc R . .
H1B H 0.0854 0.6712 0.1681 0.124 Uiso 1 1 calc R . .
H1C H 0.0427 0.6050 0.1941 0.124 Uiso 1 1 calc R . .
C2 C 0.0559(4) 0.6125(4) 0.0706(5) 0.055(2) Uani 1 1 d . . .
C3 C 0.0821(4) 0.5478(4) 0.0453(6) 0.055(2) Uani 1 1 d . . .
C4 C 0.0818(4) 0.5452(4) -0.0376(6) 0.056(2) Uani 1 1 d . . .
C5 C 0.1022(5) 0.4892(5) -0.0985(7) 0.079(3) Uani 1 1 d . . .
H5A H 0.0996 0.4444 -0.0721 0.119 Uiso 1 1 calc R . .
H5B H 0.1490 0.4973 -0.1174 0.119 Uiso 1 1 calc R . .
H5C H 0.0709 0.4902 -0.1449 0.119 Uiso 1 1 calc R . .
C6 C 0.1174(8) 0.5703(9) 0.4252(8) 0.122(5) 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
Fe1 0.0515(9) 0.0326(7) 0.0405(8) 0.000 0.000 0.0062(6)
Br1 0.0627(6) 0.0573(6) 0.0681(6) 0.0044(4) 0.0172(4) -0.0005(4)
Br2 0.1022(9) 0.0565(6) 0.1249(10) 0.0299(6) -0.0267(7) 0.0145(5)
Cl1 0.328(9) 0.189(6) 0.137(4) -0.043(4) -0.051(5) -0.035(6)
Cl2 0.65(2) 0.228(9) 0.190(7) 0.021(6) 0.007(10) -0.184(12)
Cl3 0.203(6) 0.245(7) 0.127(4) -0.029(4) 0.037(4) 0.005(5)
Cl4 0.181(8) 0.71(3) 0.286(10) -0.197(14) -0.031(7) 0.112(11)
O1 0.049(4) 0.049(4) 0.039(6) 0.000 0.000 0.000
N1 0.065(4) 0.040(3) 0.051(4) 0.002(3) -0.001(3) 0.007(3)
N2 0.053(4) 0.038(3) 0.051(4) -0.001(3) 0.001(3) 0.004(3)
C1 0.126(9) 0.063(6) 0.058(6) 0.013(5) -0.013(6) 0.006(6)
C2 0.058(5) 0.051(5) 0.055(5) 0.007(4) -0.005(4) 0.000(4)
C3 0.053(5) 0.030(4) 0.082(7) 0.011(4) -0.011(4) 0.002(3)
C4 0.041(4) 0.036(4) 0.091(7) 0.000(4) 0.012(4) -0.001(3)
C5 0.085(7) 0.043(5) 0.110(8) -0.016(5) 0.026(6) 0.003(4)
C6 0.116(11) 0.157(14) 0.092(10) 0.009(9) 0.003(8) -0.017(9)

_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 O1 1.770(2) . ?
Fe1 N1 2.112(6) . ?
Fe1 N1 2.112(6) 6_464 ?
Fe1 Br1 2.468(2) 6_464 ?
Fe1 Br1 2.468(2) . ?
Br2 C3 1.881(8) . ?
Cl1 C6 1.708(16) . ?
Cl2 C6 1.660(17) . ?
Cl3 C6 1.691(14) . ?
Cl4 C6 1.721(18) . ?
O1 Fe1 1.770(2) 11_565 ?
N1 C2 1.344(10) . ?
N1 N2 1.353(9) . ?
N2 C4 1.354(10) . ?
C1 C2 1.481(13) . ?
C2 C3 1.399(11) . ?
C3 C4 1.341(12) . ?
C4 C5 1.508(13) . ?

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 Fe1 N1 97.53(19) . . ?
O1 Fe1 N1 97.53(19) . 6_464 ?
N1 Fe1 N1 164.9(4) . 6_464 ?
O1 Fe1 Br1 106.41(4) . 6_464 ?
N1 Fe1 Br1 86.87(19) . 6_464 ?
N1 Fe1 Br1 88.89(19) 6_464 6_464 ?
O1 Fe1 Br1 106.41(4) . . ?
N1 Fe1 Br1 88.89(19) . . ?
N1 Fe1 Br1 86.87(19) 6_464 . ?
Br1 Fe1 Br1 147.18(9) 6_464 . ?
Fe1 O1 Fe1 180.0 11_565 . ?
C2 N1 N2 107.3(6) . . ?
C2 N1 Fe1 131.4(6) . . ?
N2 N1 Fe1 121.2(5) . . ?
C4 N2 N1 110.6(7) . . ?
N1 C2 C3 107.0(7) . . ?
N1 C2 C1 122.3(8) . . ?
C3 C2 C1 130.7(8) . . ?
C4 C3 C2 108.9(7) . . ?
C4 C3 Br2 126.4(6) . . ?
C2 C3 Br2 124.7(7) . . ?
C3 C4 N2 106.2(7) . . ?
C3 C4 C5 132.6(8) . . ?
N2 C4 C5 121.1(9) . . ?
Cl2 C6 Cl3 108.3(10) . . ?
Cl2 C6 Cl1 108.3(9) . . ?
Cl3 C6 Cl1 115.2(9) . . ?
Cl2 C6 Cl4 109.0(11) . . ?
Cl3 C6 Cl4 104.2(9) . . ?
Cl1 C6 Cl4 111.7(10) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.26
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.978
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.132
####################################################################### 
# 
# 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_evg040_0m
_database_code_depnum_ccdc_archive 'CCDC 942442'
_audit_update_record             
;
2013-06-02 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H24 Cl6 Fe2 N4 O2'
_chemical_formula_weight         628.79

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   8.5983(15)
_cell_length_b                   20.475(4)
_cell_length_c                   14.989(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.778(2)
_cell_angle_gamma                90.00
_cell_volume                     2592.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.59
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1272
_exptl_absorpt_coefficient_mu    1.758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3992
_exptl_absorpt_correction_T_max  0.6297
_exptl_absorpt_process_details   SADABS

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14268
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         27.07
_reflns_number_total             2841
_reflns_number_gt                2439
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0304P)²+2.9073P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2841
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0693
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 1.08160(3) 0.109939(14) 0.662156(19) 0.03692(10) Uani 1 1 d . . .
Cl1 Cl 1.16765(8) 0.01351(3) 0.63163(5) 0.06443(18) Uani 1 1 d . . .
Cl2 Cl 1.25938(7) 0.18539(3) 0.64522(4) 0.05290(15) Uani 1 1 d . . .
Cl3 Cl 0.72530(9) 0.19316(4) 0.30572(5) 0.0781(2) Uani 1 1 d . . .
O1 O 0.87346(16) 0.11385(8) 0.70201(9) 0.0425(3) Uani 1 1 d . . .
N1 N 0.9219(2) 0.13059(9) 0.54363(12) 0.0412(4) Uani 1 1 d . . .
N2 N 0.7701(2) 0.14103(9) 0.55458(11) 0.0405(4) Uani 1 1 d . . .
C1 C 1.0740(3) 0.14102(15) 0.41902(16) 0.0583(6) Uani 1 1 d . . .
H1A H 1.1208 0.1835 0.4177 0.087 Uiso 1 1 calc R . .
H1B H 1.0486 0.1239 0.3584 0.087 Uiso 1 1 calc R . .
H1C H 1.1474 0.1123 0.4562 0.087 Uiso 1 1 calc R . .
C2 C 0.9274(3) 0.14625(11) 0.45736(14) 0.0426(5) Uani 1 1 d . . .
C3 C 0.7780(3) 0.16629(11) 0.41544(14) 0.0458(5) Uani 1 1 d . . .
C4 C 0.6793(3) 0.16300(11) 0.47780(15) 0.0441(5) Uani 1 1 d . . .
C5 C 0.5094(3) 0.18037(15) 0.46796(18) 0.0622(7) Uani 1 1 d . . .
H5A H 0.4459 0.1419 0.4530 0.093 Uiso 1 1 calc R . .
H5B H 0.4824 0.2121 0.4204 0.093 Uiso 1 1 calc R . .
H5C H 0.4900 0.1983 0.5240 0.093 Uiso 1 1 calc R . .
C6 C 0.7280(2) 0.12465(12) 0.64359(14) 0.0441(5) Uani 1 1 d . . .
H6 H 0.6764 0.1626 0.6654 0.053 Uiso 1 1 calc R . .
C7 C 0.6189(3) 0.06729(14) 0.63816(17) 0.0576(6) Uani 1 1 d . . .
H7A H 0.5941 0.0597 0.6978 0.069 Uiso 1 1 calc R . .
H7B H 0.5208 0.0780 0.5974 0.069 Uiso 1 1 calc R . .
C8 C 0.6824(4) 0.00625(15) 0.6065(2) 0.0813(9) Uani 1 1 d . . .
H8A H 0.7049 0.0127 0.5467 0.122 Uiso 1 1 calc R . .
H8B H 0.6057 -0.0280 0.6048 0.122 Uiso 1 1 calc R . .
H8C H 0.7780 -0.0056 0.6474 0.122 Uiso 1 1 calc R . .

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 0.03125(16) 0.04694(18) 0.03391(16) -0.00151(12) 0.00953(11) 0.00167(12)
Cl1 0.0685(4) 0.0552(4) 0.0693(4) -0.0134(3) 0.0123(3) 0.0128(3)
Cl2 0.0485(3) 0.0633(4) 0.0492(3) -0.0003(3) 0.0150(2) -0.0125(3)
Cl3 0.0755(5) 0.1094(6) 0.0464(3) 0.0259(4) 0.0035(3) 0.0058(4)
O1 0.0300(7) 0.0645(10) 0.0337(7) -0.0006(6) 0.0081(6) 0.0008(6)
N1 0.0321(9) 0.0547(10) 0.0379(9) -0.0001(8) 0.0098(7) 0.0009(8)
N2 0.0323(9) 0.0530(10) 0.0365(9) -0.0008(8) 0.0073(7) 0.0006(7)
C1 0.0505(14) 0.0839(18) 0.0443(12) 0.0015(12) 0.0188(11) -0.0010(13)
C2 0.0419(11) 0.0507(12) 0.0361(10) -0.0019(9) 0.0091(9) -0.0033(9)
C3 0.0474(12) 0.0513(12) 0.0373(11) 0.0035(9) 0.0043(9) -0.0019(10)
C4 0.0399(11) 0.0479(12) 0.0423(11) -0.0003(9) 0.0022(9) 0.0009(9)
C5 0.0437(13) 0.0792(18) 0.0615(16) 0.0063(13) 0.0038(11) 0.0116(12)
C6 0.0328(10) 0.0639(14) 0.0362(11) -0.0015(10) 0.0080(8) 0.0012(9)
C7 0.0428(13) 0.0758(17) 0.0544(14) 0.0023(12) 0.0098(11) -0.0107(12)
C8 0.081(2) 0.074(2) 0.089(2) -0.0162(17) 0.0168(17) -0.0144(16)

_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 O1 1.9915(14) . ?
Fe1 O1 2.0016(14) 2_756 ?
Fe1 N1 2.0757(18) . ?
Fe1 Cl1 2.1868(7) . ?
Fe1 Cl2 2.2210(7) . ?
Cl3 C3 1.713(2) . ?
O1 C6 1.404(2) . ?
O1 Fe1 2.0016(14) 2_756 ?
N1 C2 1.342(3) . ?
N1 N2 1.363(2) . ?
N2 C4 1.342(3) . ?
N2 C6 1.485(3) . ?
C1 C2 1.483(3) . ?
C2 C3 1.383(3) . ?
C3 C4 1.377(3) . ?
C4 C5 1.484(3) . ?
C6 C7 1.495(3) . ?
C7 C8 1.477(4) . ?

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 Fe1 O1 72.94(6) . 2_756 ?
O1 Fe1 N1 76.16(6) . . ?
O1 Fe1 N1 146.45(6) 2_756 . ?
O1 Fe1 Cl1 117.21(5) . . ?
O1 Fe1 Cl1 103.91(5) 2_756 . ?
N1 Fe1 Cl1 101.57(6) . . ?
O1 Fe1 Cl2 133.05(5) . . ?
O1 Fe1 Cl2 94.73(5) 2_756 . ?
N1 Fe1 Cl2 96.88(5) . . ?
Cl1 Fe1 Cl2 109.70(3) . . ?
C6 O1 Fe1 124.42(12) . . ?
C6 O1 Fe1 128.37(12) . 2_756 ?
Fe1 O1 Fe1 106.87(6) . 2_756 ?
C2 N1 N2 106.62(17) . . ?
C2 N1 Fe1 137.43(14) . . ?
N2 N1 Fe1 115.10(12) . . ?
C4 N2 N1 111.48(17) . . ?
C4 N2 C6 130.24(18) . . ?
N1 N2 C6 118.22(16) . . ?
N1 C2 C3 108.14(19) . . ?
N1 C2 C1 122.8(2) . . ?
C3 C2 C1 129.0(2) . . ?
C4 C3 C2 108.38(19) . . ?
C4 C3 Cl3 125.58(18) . . ?
C2 C3 Cl3 126.01(18) . . ?
N2 C4 C3 105.38(19) . . ?
N2 C4 C5 124.7(2) . . ?
C3 C4 C5 129.9(2) . . ?
O1 C6 N2 104.92(16) . . ?
O1 C6 C7 112.7(2) . . ?
N2 C6 C7 112.60(18) . . ?
C8 C7 C6 114.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.07
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_evg007_0m
_database_code_depnum_ccdc_archive 'CCDC 942443'
_audit_update_record             
;
2013-06-02 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 Cl4 Fe2 I2 N4 O2'
_chemical_formula_weight         783.64

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'
O O 0.0106 0.0060 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   8.5950(6)
_cell_length_b                   9.6865(7)
_cell_length_c                   15.7769(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.3500(10)
_cell_angle_gamma                90.00
_cell_volume                     1296.06(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.008
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    3.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5547
_exptl_absorpt_correction_T_max  0.7337
_exptl_absorpt_process_details   SADABS

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14277
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         27.17
_reflns_number_total             2878
_reflns_number_gt                2175
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0407P)²+1.5127P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2878
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0906
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.66288(6) 0.18704(6) 0.83262(4) 0.04924(16) Uani 1 1 d . . .
I1 I 1.00937(4) 0.40962(4) 1.18398(2) 0.07525(14) Uani 1 1 d . . .
Cl1 Cl 0.5741(2) -0.01237(18) 0.86614(12) 0.1171(6) Uani 1 1 d . . .
Cl2 Cl 0.48894(16) 0.35170(18) 0.84518(8) 0.0916(5) Uani 1 1 d . . .
O1 O 0.8738(3) 0.1868(3) 0.79567(17) 0.0512(6) Uani 1 1 d . . .
N1 N 0.8155(3) 0.2341(3) 0.9444(2) 0.0494(7) Uani 1 1 d . . .
N2 N 0.9702(3) 0.2476(4) 0.9344(2) 0.0500(7) Uani 1 1 d . . .
C1 C 0.6561(5) 0.2818(6) 1.0591(3) 0.0683(12) Uani 1 1 d . . .
H1A H 0.6049 0.3694 1.0472 0.102 Uiso 1 1 calc R . .
H1B H 0.6778 0.2673 1.1200 0.102 Uiso 1 1 calc R . .
H1C H 0.5885 0.2096 1.0327 0.102 Uiso 1 1 calc R . .
C2 C 0.8060(4) 0.2804(4) 1.0240(2) 0.0486(9) Uani 1 1 d . . .
C3 C 0.9558(5) 0.3227(4) 1.0631(3) 0.0515(9) Uani 1 1 d . . .
C4 C 1.0574(4) 0.3010(4) 1.0050(3) 0.0510(9) Uani 1 1 d . . .
C5 C 1.2299(5) 0.3280(6) 1.0133(3) 0.0711(13) Uani 1 1 d . . .
H5A H 1.2869 0.2438 1.0280 0.107 Uiso 1 1 calc R . .
H5B H 1.2604 0.3954 1.0575 0.107 Uiso 1 1 calc R . .
H5C H 1.2536 0.3621 0.9597 0.107 Uiso 1 1 calc R . .
C6 C 1.0147(4) 0.1909(5) 0.8549(3) 0.0553(10) Uani 1 1 d . . .
H6 H 1.0902 0.2527 0.8338 0.066 Uiso 1 1 calc R . .
C7 C 1.0869(7) 0.0480(6) 0.8710(4) 0.0903(17) Uani 1 1 d . . .
H7A H 1.0100 -0.0137 0.8878 0.135 Uiso 1 1 calc R . .
H7B H 1.1764 0.0532 0.9160 0.135 Uiso 1 1 calc R . .
H7C H 1.1197 0.0146 0.8195 0.135 Uiso 1 1 calc R . .

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 0.0410(3) 0.0551(3) 0.0542(3) 0.0086(3) 0.0156(2) -0.0044(2)
I1 0.0784(2) 0.0871(3) 0.0582(2) -0.00337(15) 0.00523(15) -0.01081(17)
Cl1 0.1324(13) 0.0989(11) 0.1140(12) 0.0392(9) 0.0019(10) -0.0619(10)
Cl2 0.0856(9) 0.1335(12) 0.0614(7) 0.0179(8) 0.0289(6) 0.0563(9)
O1 0.0398(13) 0.0601(16) 0.0558(15) 0.0049(13) 0.0141(11) 0.0058(12)
N1 0.0389(15) 0.0564(19) 0.0557(19) 0.0038(15) 0.0159(14) -0.0031(14)
N2 0.0348(15) 0.061(2) 0.0560(19) 0.0087(16) 0.0127(13) 0.0033(14)
C1 0.048(2) 0.095(3) 0.066(3) -0.003(3) 0.021(2) -0.008(2)
C2 0.0441(19) 0.053(2) 0.052(2) 0.0089(18) 0.0159(16) -0.0026(16)
C3 0.049(2) 0.050(2) 0.055(2) 0.0082(18) 0.0085(17) 0.0007(17)
C4 0.0411(19) 0.052(2) 0.061(2) 0.0133(19) 0.0101(17) 0.0018(17)
C5 0.039(2) 0.099(4) 0.074(3) 0.013(3) 0.007(2) -0.003(2)
C6 0.042(2) 0.066(3) 0.059(2) 0.004(2) 0.0128(17) 0.0092(18)
C7 0.092(4) 0.090(4) 0.086(4) 0.001(3) 0.007(3) 0.046(3)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O1 1.992(2) . ?
Fe1 O1 1.997(3) 2_656 ?
Fe1 N1 2.071(3) . ?
Fe1 Cl1 2.1735(14) . ?
Fe1 Cl2 2.2169(14) . ?
I1 C3 2.067(4) . ?
O1 C6 1.405(5) . ?
O1 Fe1 1.997(3) 2_656 ?
N1 C2 1.348(5) . ?
N1 N2 1.371(4) . ?
N2 C4 1.341(5) . ?
N2 C6 1.475(5) . ?
C1 C2 1.482(5) . ?
C2 C3 1.395(5) . ?
C3 C4 1.381(5) . ?
C4 C5 1.491(5) . ?
C6 C7 1.521(6) . ?

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 Fe1 O1 72.83(12) . 2_656 ?
O1 Fe1 N1 76.65(11) . . ?
O1 Fe1 N1 146.87(11) 2_656 . ?
O1 Fe1 Cl1 116.26(10) . . ?
O1 Fe1 Cl1 104.00(9) 2_656 . ?
N1 Fe1 Cl1 100.78(10) . . ?
O1 Fe1 Cl2 133.29(9) . . ?
O1 Fe1 Cl2 95.37(8) 2_656 . ?
N1 Fe1 Cl2 96.23(10) . . ?
Cl1 Fe1 Cl2 110.43(8) . . ?
C6 O1 Fe1 122.2(2) . . ?
C6 O1 Fe1 130.6(2) . 2_656 ?
Fe1 O1 Fe1 107.17(12) . 2_656 ?
C2 N1 N2 106.4(3) . . ?
C2 N1 Fe1 137.8(2) . . ?
N2 N1 Fe1 114.5(2) . . ?
C4 N2 N1 111.2(3) . . ?
C4 N2 C6 131.5(3) . . ?
N1 N2 C6 116.9(3) . . ?
N1 C2 C3 108.6(3) . . ?
N1 C2 C1 122.5(4) . . ?
C3 C2 C1 128.9(4) . . ?
C4 C3 C2 107.4(4) . . ?
C4 C3 I1 127.2(3) . . ?
C2 C3 I1 125.4(3) . . ?
N2 C4 C3 106.4(3) . . ?
N2 C4 C5 123.6(4) . . ?
C3 C4 C5 130.0(4) . . ?
O1 C6 N2 105.1(3) . . ?
O1 C6 C7 111.7(4) . . ?
N2 C6 C7 110.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.17
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.059
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.077
####################################################################### 
# 
# 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_evg006_0m
_database_code_depnum_ccdc_archive 'CCDC 942444'
_audit_update_record             
;
2013-06-02 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 Br6 Fe2 N4 O2'
_chemical_formula_weight         867.50

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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   8.6395(6)
_cell_length_b                   9.7711(7)
_cell_length_c                   15.8621(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.6650(10)
_cell_angle_gamma                90.00
_cell_volume                     1301.13(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            dark-red
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             820
_exptl_absorpt_coefficient_mu    10.344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2884
_exptl_absorpt_correction_T_max  0.5757
_exptl_absorpt_process_details   SADABS

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14343
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         27.12
_reflns_number_total             2886
_reflns_number_gt                2155
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0255P)²+2.6002P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2886
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.83300(6) 0.69228(6) 0.16956(4) 0.03957(15) Uani 1 1 d . . .
Br1 Br 1.02912(6) 0.85604(6) 0.15863(3) 0.06427(16) Uani 1 1 d . . .
Br2 Br 0.91498(9) 0.47484(7) 0.14013(4) 0.0942(2) Uani 1 1 d . . .
Br3 Br 0.47469(7) 0.90494(7) -0.18007(3) 0.07360(18) Uani 1 1 d . . .
O1 O 0.6230(3) 0.6991(3) 0.20118(16) 0.0412(6) Uani 1 1 d . . .
N1 N 0.6739(4) 0.7377(3) 0.0522(2) 0.0418(8) Uani 1 1 d . . .
N2 N 0.5220(4) 0.7608(4) 0.0599(2) 0.0409(7) Uani 1 1 d . . .
C1 C 0.8257(5) 0.7712(6) -0.0614(3) 0.0627(13) Uani 1 1 d . . .
H1A H 0.8758 0.8594 -0.0573 0.094 Uiso 1 1 calc R . .
H1B H 0.7976 0.7425 -0.1209 0.094 Uiso 1 1 calc R . .
H1C H 0.8980 0.7062 -0.0277 0.094 Uiso 1 1 calc R . .
C2 C 0.6797(5) 0.7798(4) -0.0276(3) 0.0439(9) Uani 1 1 d . . .
C3 C 0.5293(5) 0.8273(4) -0.0691(3) 0.0450(10) Uani 1 1 d . . .
C4 C 0.4309(5) 0.8144(4) -0.0128(3) 0.0433(9) Uani 1 1 d . . .
C5 C 0.2608(5) 0.8522(5) -0.0233(3) 0.0582(12) Uani 1 1 d . . .
H5A H 0.1963 0.7712 -0.0336 0.087 Uiso 1 1 calc R . .
H5B H 0.2290 0.9135 -0.0715 0.087 Uiso 1 1 calc R . .
H5C H 0.2473 0.8964 0.0286 0.087 Uiso 1 1 calc R . .
C6 C 0.4792(4) 0.7066(5) 0.1380(3) 0.0450(10) Uani 1 1 d . . .
H6 H 0.4065 0.7702 0.1571 0.054 Uiso 1 1 calc R . .
C7 C 0.4008(7) 0.5675(6) 0.1195(3) 0.0800(17) Uani 1 1 d . . .
H7A H 0.4759 0.5034 0.1062 0.120 Uiso 1 1 calc R . .
H7B H 0.3104 0.5744 0.0711 0.120 Uiso 1 1 calc R . .
H7C H 0.3665 0.5365 0.1696 0.120 Uiso 1 1 calc R . .

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 0.0321(3) 0.0465(3) 0.0417(3) -0.0052(2) 0.0120(2) 0.0044(2)
Br1 0.0510(3) 0.0931(4) 0.0520(3) -0.0046(2) 0.0188(2) -0.0237(3)
Br2 0.1092(5) 0.0712(4) 0.0948(4) -0.0288(3) 0.0089(4) 0.0396(3)
Br3 0.0761(4) 0.0931(4) 0.0484(3) 0.0140(3) 0.0084(2) 0.0069(3)
O1 0.0294(13) 0.0549(17) 0.0399(14) -0.0022(12) 0.0093(11) -0.0033(12)
N1 0.0329(17) 0.052(2) 0.0417(18) -0.0032(16) 0.0110(14) 0.0018(15)
N2 0.0291(16) 0.054(2) 0.0414(17) -0.0035(16) 0.0120(14) 0.0002(14)
C1 0.047(3) 0.093(4) 0.053(3) -0.002(3) 0.020(2) 0.001(3)
C2 0.039(2) 0.050(2) 0.045(2) -0.0057(18) 0.0145(18) -0.0019(18)
C3 0.044(2) 0.049(2) 0.041(2) -0.0027(18) 0.0063(18) -0.0034(19)
C4 0.036(2) 0.049(2) 0.043(2) -0.0082(18) 0.0050(17) -0.0036(18)
C5 0.035(2) 0.072(3) 0.065(3) -0.006(2) 0.007(2) 0.008(2)
C6 0.0299(19) 0.063(3) 0.042(2) -0.0016(19) 0.0085(16) -0.0032(18)
C7 0.074(4) 0.095(4) 0.063(3) 0.006(3) 0.001(3) -0.046(3)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O1 1.996(3) 2_655 ?
Fe1 O1 1.995(3) . ?
Fe1 N1 2.083(3) . ?
Fe1 Br2 2.3216(8) . ?
Fe1 Br1 2.3665(7) . ?
Br3 C3 1.871(4) . ?
O1 C6 1.401(4) . ?
O1 Fe1 1.996(3) 2_655 ?
N1 C2 1.343(5) . ?
N1 N2 1.365(4) . ?
N2 C4 1.340(5) . ?
N2 C6 1.473(5) . ?
C1 C2 1.485(6) . ?
C2 C3 1.390(6) . ?
C3 C4 1.377(6) . ?
C4 C5 1.486(5) . ?
C6 C7 1.516(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 O1 72.81(11) 2_655 . ?
O1 Fe1 N1 146.70(12) 2_655 . ?
O1 Fe1 N1 76.71(11) . . ?
O1 Fe1 Br2 104.11(8) 2_655 . ?
O1 Fe1 Br2 114.83(9) . . ?
N1 Fe1 Br2 100.57(9) . . ?
O1 Fe1 Br1 94.98(8) 2_655 . ?
O1 Fe1 Br1 134.87(8) . . ?
N1 Fe1 Br1 97.08(9) . . ?
Br2 Fe1 Br1 110.26(3) . . ?
C6 O1 Fe1 131.1(2) . 2_655 ?
C6 O1 Fe1 121.9(2) . . ?
Fe1 O1 Fe1 107.06(11) 2_655 . ?
C2 N1 N2 106.5(3) . . ?
C2 N1 Fe1 138.0(3) . . ?
N2 N1 Fe1 113.6(2) . . ?
C4 N2 N1 111.7(3) . . ?
C4 N2 C6 130.7(3) . . ?
N1 N2 C6 117.0(3) . . ?
N1 C2 C3 108.1(3) . . ?
N1 C2 C1 123.1(4) . . ?
C3 C2 C1 128.7(4) . . ?
C4 C3 C2 108.2(4) . . ?
C4 C3 Br3 126.2(3) . . ?
C2 C3 Br3 125.5(3) . . ?
N2 C4 C3 105.5(3) . . ?
N2 C4 C5 123.9(4) . . ?
C3 C4 C5 130.6(4) . . ?
O1 C6 N2 105.3(3) . . ?
O1 C6 C7 111.8(4) . . ?
N2 C6 C7 110.4(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.12
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.838
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.084
####################################################################### 
# 
# 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_evg084_0m
_database_code_depnum_ccdc_archive 'CCDC 942445'
_audit_update_record             
;
2013-06-02 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 Br2 Cl2 Fe N4'
_chemical_formula_weight         502.86

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.1777(13)
_cell_length_b                   8.7316(9)
_cell_length_c                   17.3452(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.4070(10)
_cell_angle_gamma                90.00
_cell_volume                     1842.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            light-blue
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    5.443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1932
_exptl_absorpt_correction_T_max  0.3110
_exptl_absorpt_process_details   SADABS

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19914
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         27.09
_reflns_number_total             4050
_reflns_number_gt                3201
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0457P)²+2.1565P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4050
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.17276(4) 0.21480(6) 0.44846(3) 0.03743(15) Uani 1 1 d . . .
Br1 Br -0.17048(4) 0.42458(6) 0.21701(3) 0.06252(16) Uani 1 1 d . . .
Br2 Br 0.61254(3) 0.47407(6) 0.37903(3) 0.05735(15) Uani 1 1 d . . .
Cl1 Cl 0.20580(13) 0.00902(14) 0.37417(11) 0.0887(5) Uani 1 1 d . . .
Cl2 Cl 0.13636(10) 0.20965(17) 0.57340(7) 0.0682(4) Uani 1 1 d . . .
N1 N 0.0662(2) 0.3539(3) 0.38239(15) 0.0313(6) Uani 1 1 d . . .
N2 N 0.0966(2) 0.4943(3) 0.35429(15) 0.0290(6) Uani 1 1 d . . .
N3 N 0.3015(2) 0.3666(3) 0.43028(16) 0.0318(6) Uani 1 1 d . . .
N4 N 0.2869(2) 0.5025(3) 0.39205(16) 0.0293(6) Uani 1 1 d . . .
C1 C -0.0805(4) 0.1640(5) 0.3542(3) 0.0529(10) Uani 1 1 d . . .
H1A H -0.0574 0.0920 0.3164 0.079 Uiso 1 1 calc R . .
H1B H -0.1587 0.1770 0.3492 0.079 Uiso 1 1 calc R . .
H1C H -0.0608 0.1264 0.4049 0.079 Uiso 1 1 calc R . .
C2 C -0.0254(3) 0.3145(4) 0.34205(19) 0.0347(8) Uani 1 1 d . . .
C3 C -0.0535(3) 0.4302(4) 0.29000(19) 0.0349(8) Uani 1 1 d . . .
C4 C 0.0243(3) 0.5447(4) 0.29875(19) 0.0341(7) Uani 1 1 d . . .
C5 C 0.0337(4) 0.6947(5) 0.2596(2) 0.0546(11) Uani 1 1 d . . .
H5A H 0.0338 0.7752 0.2973 0.082 Uiso 1 1 calc R . .
H5B H -0.0275 0.7080 0.2235 0.082 Uiso 1 1 calc R . .
H5C H 0.1009 0.6979 0.2326 0.082 Uiso 1 1 calc R . .
C6 C 0.4569(4) 0.1967(5) 0.4679(3) 0.0543(11) Uani 1 1 d . . .
H6A H 0.4155 0.1704 0.5120 0.082 Uiso 1 1 calc R . .
H6B H 0.5321 0.2151 0.4841 0.082 Uiso 1 1 calc R . .
H6C H 0.4534 0.1140 0.4315 0.082 Uiso 1 1 calc R . .
C7 C 0.4097(3) 0.3377(4) 0.43106(19) 0.0351(8) Uani 1 1 d . . .
C8 C 0.4624(3) 0.4562(4) 0.39487(19) 0.0341(7) Uani 1 1 d . . .
C9 C 0.3840(3) 0.5607(4) 0.36990(19) 0.0322(7) Uani 1 1 d . . .
C10 C 0.3950(4) 0.7067(5) 0.3270(3) 0.0525(10) Uani 1 1 d . . .
H10A H 0.3593 0.6973 0.2769 0.079 Uiso 1 1 calc R . .
H10B H 0.4714 0.7293 0.3216 0.079 Uiso 1 1 calc R . .
H10C H 0.3614 0.7880 0.3549 0.079 Uiso 1 1 calc R . .
C11 C 0.1824(3) 0.5825(4) 0.39409(19) 0.0294(7) Uani 1 1 d . . .
H11 H 0.1900 0.6787 0.3657 0.035 Uiso 1 1 calc R . .
C12 C 0.1525(3) 0.6236(5) 0.4760(2) 0.0417(8) Uani 1 1 d . . .
H12A H 0.0844 0.6792 0.4745 0.063 Uiso 1 1 calc R . .
H12B H 0.2095 0.6859 0.4996 0.063 Uiso 1 1 calc R . .
H12C H 0.1447 0.5316 0.5056 0.063 Uiso 1 1 calc R . .

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 0.0362(3) 0.0299(3) 0.0458(3) 0.0123(2) -0.0033(2) -0.0009(2)
Br1 0.0376(2) 0.0893(4) 0.0585(3) -0.0099(2) -0.02391(19) 0.0137(2)
Br2 0.0251(2) 0.0797(3) 0.0674(3) -0.0148(2) 0.00313(18) -0.00386(18)
Cl1 0.0830(10) 0.0389(6) 0.1432(14) -0.0259(7) -0.0082(9) 0.0076(6)
Cl2 0.0567(7) 0.0977(9) 0.0501(6) 0.0369(6) 0.0000(5) -0.0010(6)
N1 0.0336(15) 0.0275(14) 0.0324(14) 0.0041(11) -0.0052(12) -0.0030(11)
N2 0.0282(14) 0.0294(14) 0.0288(13) 0.0047(11) -0.0066(11) 0.0002(11)
N3 0.0294(15) 0.0287(14) 0.0371(15) 0.0058(12) -0.0016(12) 0.0012(11)
N4 0.0259(14) 0.0271(14) 0.0348(14) 0.0048(11) 0.0000(11) 0.0000(11)
C1 0.045(2) 0.050(2) 0.063(3) -0.005(2) -0.007(2) -0.0152(19)
C2 0.0277(17) 0.0418(19) 0.0342(17) -0.0066(15) -0.0018(14) -0.0029(14)
C3 0.0248(17) 0.047(2) 0.0319(17) -0.0068(15) -0.0071(13) 0.0100(14)
C4 0.0325(18) 0.0412(19) 0.0283(16) 0.0033(14) -0.0039(14) 0.0084(14)
C5 0.063(3) 0.051(2) 0.048(2) 0.020(2) -0.012(2) 0.009(2)
C6 0.043(2) 0.054(3) 0.065(3) 0.011(2) -0.011(2) 0.0127(19)
C7 0.0344(19) 0.0374(18) 0.0330(17) -0.0040(15) -0.0046(14) 0.0073(14)
C8 0.0258(17) 0.0426(19) 0.0337(17) -0.0095(15) 0.0002(13) -0.0021(14)
C9 0.0306(18) 0.0362(18) 0.0299(16) -0.0053(14) 0.0019(13) -0.0065(14)
C10 0.047(2) 0.049(2) 0.062(3) 0.015(2) 0.010(2) -0.0080(18)
C11 0.0277(17) 0.0235(15) 0.0366(17) 0.0030(13) -0.0039(13) 0.0008(12)
C12 0.037(2) 0.044(2) 0.043(2) -0.0105(17) -0.0047(16) 0.0067(16)

_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 N1 2.085(3) . ?
Fe1 N3 2.086(3) . ?
Fe1 Cl2 2.2307(13) . ?
Fe1 Cl1 2.2571(14) . ?
Br1 C3 1.867(3) . ?
Br2 C8 1.866(3) . ?
N1 C2 1.336(4) . ?
N1 N2 1.375(4) . ?
N2 C4 1.351(4) . ?
N2 C11 1.450(4) . ?
N3 C7 1.341(4) . ?
N3 N4 1.367(4) . ?
N4 C9 1.356(4) . ?
N4 C11 1.454(4) . ?
C1 C2 1.495(5) . ?
C2 C3 1.388(5) . ?
C3 C4 1.381(5) . ?
C4 C5 1.482(5) . ?
C6 C7 1.491(5) . ?
C7 C8 1.382(5) . ?
C8 C9 1.378(5) . ?
C9 C10 1.485(5) . ?
C11 C12 1.525(5) . ?

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
N1 Fe1 N3 90.06(11) . . ?
N1 Fe1 Cl2 113.65(9) . . ?
N3 Fe1 Cl2 109.92(9) . . ?
N1 Fe1 Cl1 105.77(9) . . ?
N3 Fe1 Cl1 105.45(9) . . ?
Cl2 Fe1 Cl1 125.88(6) . . ?
C2 N1 N2 106.0(3) . . ?
C2 N1 Fe1 128.6(2) . . ?
N2 N1 Fe1 122.9(2) . . ?
C4 N2 N1 111.5(3) . . ?
C4 N2 C11 127.0(3) . . ?
N1 N2 C11 120.3(2) . . ?
C7 N3 N4 106.0(3) . . ?
C7 N3 Fe1 128.5(2) . . ?
N4 N3 Fe1 122.8(2) . . ?
C9 N4 N3 111.5(3) . . ?
C9 N4 C11 127.0(3) . . ?
N3 N4 C11 120.0(3) . . ?
N1 C2 C3 109.3(3) . . ?
N1 C2 C1 121.5(3) . . ?
C3 C2 C1 129.2(3) . . ?
C4 C3 C2 107.8(3) . . ?
C4 C3 Br1 126.5(3) . . ?
C2 C3 Br1 125.6(3) . . ?
N2 C4 C3 105.4(3) . . ?
N2 C4 C5 123.7(3) . . ?
C3 C4 C5 130.9(3) . . ?
N3 C7 C8 109.3(3) . . ?
N3 C7 C6 121.3(3) . . ?
C8 C7 C6 129.4(3) . . ?
C9 C8 C7 108.0(3) . . ?
C9 C8 Br2 124.7(3) . . ?
C7 C8 Br2 127.3(3) . . ?
N4 C9 C8 105.3(3) . . ?
N4 C9 C10 124.2(3) . . ?
C8 C9 C10 130.5(3) . . ?
N2 C11 N4 110.4(3) . . ?
N2 C11 C12 111.9(3) . . ?
N4 C11 C12 112.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.09
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.531
_refine_diff_density_min         -1.016
_refine_diff_density_rms         0.125
####################################################################### 
# 
# 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_evg085_2_abs_cor
_database_code_depnum_ccdc_archive 'CCDC 942446'
_audit_update_record             
;
2013-06-02 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 Br4 Fe N4'
_chemical_formula_weight         591.78

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.247(4)
_cell_length_b                   8.932(3)
_cell_length_c                   17.420(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.930(3)
_cell_angle_gamma                90.00
_cell_volume                     1904.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.064
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    9.181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1168
_exptl_absorpt_correction_T_max  0.2487
_exptl_absorpt_process_details   SADABS

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18641
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         26.38
_reflns_number_total             3870
_reflns_number_gt                3148
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0458P)²+4.4370P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3870
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.32640(5) 0.72106(7) 0.05312(4) 0.03497(17) Uani 1 1 d . . .
Br1 Br -0.11477(4) 0.96618(8) 0.12003(4) 0.05931(19) Uani 1 1 d . . .
Br2 Br 0.66566(4) 0.92918(8) 0.28199(3) 0.06146(19) Uani 1 1 d . . .
Br3 Br 0.29202(6) 0.50617(7) 0.13137(5) 0.0776(2) Uani 1 1 d . . .
Br4 Br 0.36471(5) 0.71044(8) -0.07900(3) 0.0624(2) Uani 1 1 d . . .
N1 N 0.1969(3) 0.8656(4) 0.0706(2) 0.0316(8) Uani 1 1 d . . .
N2 N 0.2091(3) 0.9979(4) 0.1097(2) 0.0285(8) Uani 1 1 d . . .
N3 N 0.4315(3) 0.8581(4) 0.1182(2) 0.0312(8) Uani 1 1 d . . .
N4 N 0.3986(3) 0.9926(4) 0.1477(2) 0.0284(7) Uani 1 1 d . . .
C1 C 0.0445(4) 0.7000(6) 0.0304(3) 0.0510(13) Uani 1 1 d . . .
H1A H 0.0826 0.6810 -0.0158 0.076 Uiso 1 1 calc R . .
H1B H -0.0318 0.7145 0.0181 0.076 Uiso 1 1 calc R . .
H1C H 0.0534 0.6163 0.0646 0.076 Uiso 1 1 calc R . .
C2 C 0.0896(4) 0.8367(5) 0.0682(2) 0.0340(10) Uani 1 1 d . . .
C3 C 0.0352(3) 0.9508(5) 0.1048(2) 0.0337(10) Uani 1 1 d . . .
C4 C 0.1117(3) 1.0537(5) 0.1307(2) 0.0317(9) Uani 1 1 d . . .
C5 C 0.0980(4) 1.1962(6) 0.1734(3) 0.0517(13) Uani 1 1 d . . .
H5A H 0.1399 1.1921 0.2210 0.078 Uiso 1 1 calc R . .
H5B H 0.0222 1.2104 0.1838 0.078 Uiso 1 1 calc R . .
H5C H 0.1231 1.2781 0.1430 0.078 Uiso 1 1 calc R . .
C6 C 0.5813(4) 0.6773(6) 0.1434(3) 0.0518(13) Uani 1 1 d . . .
H6A H 0.5513 0.6310 0.0977 0.078 Uiso 1 1 calc R . .
H6B H 0.5728 0.6114 0.1863 0.078 Uiso 1 1 calc R . .
H6C H 0.6576 0.6971 0.1372 0.078 Uiso 1 1 calc R . .
C7 C 0.5231(3) 0.8204(5) 0.1574(3) 0.0335(10) Uani 1 1 d . . .
C8 C 0.5489(3) 0.9328(5) 0.2107(2) 0.0344(10) Uani 1 1 d . . .
C9 C 0.4696(3) 1.0420(5) 0.2035(2) 0.0308(9) Uani 1 1 d . . .
C10 C 0.4576(4) 1.1855(6) 0.2446(3) 0.0492(13) Uani 1 1 d . . .
H10A H 0.4596 1.2667 0.2086 0.074 Uiso 1 1 calc R . .
H10B H 0.5163 1.1965 0.2821 0.074 Uiso 1 1 calc R . .
H10C H 0.3891 1.1866 0.2698 0.074 Uiso 1 1 calc R . .
C11 C 0.3127(3) 1.0783(5) 0.1086(2) 0.0290(9) Uani 1 1 d . . .
H11 H 0.3037 1.1712 0.1376 0.035 Uiso 1 1 calc R . .
C12 C 0.3433(4) 1.1220(6) 0.0277(3) 0.0421(11) Uani 1 1 d . . .
H12A H 0.4122 1.1734 0.0297 0.063 Uiso 1 1 calc R . .
H12B H 0.2881 1.1866 0.0056 0.063 Uiso 1 1 calc R . .
H12C H 0.3490 1.0336 -0.0032 0.063 Uiso 1 1 calc R . .

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 0.0324(3) 0.0288(3) 0.0435(4) -0.0104(3) -0.0026(3) 0.0008(3)
Br1 0.0217(2) 0.0814(4) 0.0749(4) 0.0129(3) 0.0021(2) 0.0028(2)
Br2 0.0340(3) 0.0894(5) 0.0591(3) 0.0100(3) -0.0245(2) -0.0101(3)
Br3 0.0762(5) 0.0354(3) 0.1209(6) 0.0186(3) -0.0036(4) -0.0044(3)
Br4 0.0489(3) 0.0896(5) 0.0486(3) -0.0305(3) 0.0007(2) -0.0034(3)
N1 0.0245(18) 0.0285(18) 0.041(2) -0.0071(16) -0.0036(15) -0.0022(14)
N2 0.0228(17) 0.0262(18) 0.0363(19) -0.0040(15) -0.0013(14) -0.0010(14)
N3 0.0288(19) 0.0289(19) 0.0355(19) -0.0048(15) -0.0048(15) 0.0045(15)
N4 0.0245(17) 0.0281(18) 0.0322(18) -0.0026(14) -0.0073(14) 0.0003(14)
C1 0.042(3) 0.050(3) 0.059(3) -0.008(3) -0.011(2) -0.011(2)
C2 0.029(2) 0.038(2) 0.035(2) 0.0045(19) -0.0064(18) -0.0057(19)
C3 0.023(2) 0.043(3) 0.034(2) 0.010(2) -0.0026(17) 0.0003(19)
C4 0.026(2) 0.036(2) 0.033(2) 0.0034(19) 0.0009(17) 0.0054(18)
C5 0.044(3) 0.050(3) 0.062(3) -0.012(3) 0.008(3) 0.010(2)
C6 0.041(3) 0.049(3) 0.064(3) 0.004(3) -0.003(3) 0.017(2)
C7 0.022(2) 0.039(2) 0.039(2) 0.005(2) -0.0022(18) 0.0015(18)
C8 0.024(2) 0.044(3) 0.035(2) 0.007(2) -0.0098(18) -0.0064(19)
C9 0.028(2) 0.037(2) 0.028(2) -0.0009(18) -0.0048(17) -0.0091(18)
C10 0.052(3) 0.051(3) 0.044(3) -0.016(2) -0.011(2) -0.009(2)
C11 0.023(2) 0.025(2) 0.039(2) -0.0030(17) -0.0052(17) 0.0004(16)
C12 0.035(3) 0.046(3) 0.045(3) 0.008(2) -0.006(2) -0.009(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
Fe1 N1 2.075(4) . ?
Fe1 N3 2.083(4) . ?
Fe1 Br4 2.3662(11) . ?
Fe1 Br3 2.3997(10) . ?
Br1 C3 1.869(4) . ?
Br2 C8 1.861(4) . ?
N1 C2 1.339(5) . ?
N1 N2 1.369(5) . ?
N2 C4 1.355(5) . ?
N2 C11 1.460(5) . ?
N3 C7 1.336(5) . ?
N3 N4 1.373(5) . ?
N4 C9 1.355(5) . ?
N4 C11 1.452(5) . ?
C1 C2 1.484(7) . ?
C2 C3 1.385(7) . ?
C3 C4 1.378(6) . ?
C4 C5 1.486(7) . ?
C6 C7 1.488(7) . ?
C7 C8 1.397(6) . ?
C8 C9 1.379(6) . ?
C9 C10 1.479(7) . ?
C11 C12 1.520(6) . ?

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
N1 Fe1 N3 90.91(14) . . ?
N1 Fe1 Br4 110.17(11) . . ?
N3 Fe1 Br4 114.42(11) . . ?
N1 Fe1 Br3 105.37(11) . . ?
N3 Fe1 Br3 106.14(11) . . ?
Br4 Fe1 Br3 124.39(4) . . ?
C2 N1 N2 105.8(3) . . ?
C2 N1 Fe1 129.0(3) . . ?
N2 N1 Fe1 122.6(3) . . ?
C4 N2 N1 111.7(3) . . ?
C4 N2 C11 126.6(4) . . ?
N1 N2 C11 119.9(3) . . ?
C7 N3 N4 106.3(3) . . ?
C7 N3 Fe1 128.5(3) . . ?
N4 N3 Fe1 122.3(3) . . ?
C9 N4 N3 111.4(3) . . ?
C9 N4 C11 127.0(4) . . ?
N3 N4 C11 120.1(3) . . ?
N1 C2 C3 109.3(4) . . ?
N1 C2 C1 121.5(4) . . ?
C3 C2 C1 129.2(4) . . ?
C4 C3 C2 108.0(4) . . ?
C4 C3 Br1 124.4(4) . . ?
C2 C3 Br1 127.6(3) . . ?
N2 C4 C3 105.1(4) . . ?
N2 C4 C5 124.4(4) . . ?
C3 C4 C5 130.4(4) . . ?
N3 C7 C8 109.1(4) . . ?
N3 C7 C6 122.1(4) . . ?
C8 C7 C6 128.8(4) . . ?
C9 C8 C7 107.7(4) . . ?
C9 C8 Br2 126.6(3) . . ?
C7 C8 Br2 125.6(3) . . ?
N4 C9 C8 105.6(4) . . ?
N4 C9 C10 123.9(4) . . ?
C8 C9 C10 130.5(4) . . ?
N4 C11 N2 110.5(3) . . ?
N4 C11 C12 111.9(4) . . ?
N2 C11 C12 112.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.725
_refine_diff_density_min         -1.018
_refine_diff_density_rms         0.128
####################################################################### 
# 
# 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_EVG149
_database_code_depnum_ccdc_archive 'CCDC 1521056'
_audit_update_record             
;
2016-12-06 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            EVG042
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H16 Cl5 Fe N4 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         441.37

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.487(3)
_cell_length_b                   8.7651(10)
_cell_length_c                   8.5302(10)
_cell_angle_alpha                90
_cell_angle_beta                 110.281(3)
_cell_angle_gamma                90
_cell_volume                     1717.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9934
_cell_measurement_theta_min      3.3326
_cell_measurement_theta_max      27.5654
_cell_measurement_temperature    298

_exptl_crystal_description       Polygon
_exptl_crystal_colour            'lustrous intense red'
_exptl_crystal_size_max          0.699
_exptl_crystal_size_mid          0.617
_exptl_crystal_size_min          0.466
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             892

_exptl_absorpt_coefficient_mu    1.657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2015)'
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      298

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'Bruker D8 Quest CMOS'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            17884
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         27.61
_diffrn_reflns_theta_full        27.61
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;

Refined as a 2-component twin.
;

_reflns_number_total             1975
_reflns_number_gt                1758
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0889
_refine_ls_goodness_of_fit_ref   1.239
_refine_ls_restrained_S_all      1.239
_refine_ls_number_reflns         1975
_refine_ls_number_parameters     108
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0099P)²+7.6418P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.385
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.1'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe1 0 0.22113(8) 0.75 0.02265(17) Uani d T P S 1 . .
H H1 -0.010(3) -0.069(7) 0.842(7) 0.09(2) Uiso d . . . 1 . .
Cl Cl1 0 0.48459(13) 0.75 0.0281(3) Uani d T P S 1 . .
Cl Cl2 0.05246(4) 0.21605(12) 1.03837(11) 0.0331(2) Uani d . . . 1 . .
H H2 0.050(2) 0.368(5) 0.513(6) 0.042(13) Uiso d . . . 1 . .
Cl Cl4 0.24280(4) 0.20467(16) 0.74126(17) 0.0534(3) Uani d . . . 1 . .
O O1 0 -0.0148(4) 0.75 0.0377(9) Uani d T P S 1 . .
N N1 0.07895(13) 0.2184(4) 0.6914(4) 0.0271(7) Uani d . . . 1 . .
N N2 0.08257(13) 0.3228(4) 0.5764(4) 0.0284(7) Uani d . . . 1 . .
C C1 0.13321(16) 0.1633(4) 0.7631(5) 0.0272(8) Uani d . . . 1 . .
C C2 0.16950(15) 0.2366(4) 0.6907(5) 0.0290(8) Uani d . . . 1 . .
C C3 0.13661(16) 0.3366(4) 0.5728(5) 0.0284(8) Uani d . . . 1 . .
C C4 0.14903(18) 0.0399(5) 0.8912(6) 0.0419(10) Uani d . . . 1 . .
H H4A 0.1607 0.0843 1.0007 0.063 Uiso calc . . GR 1 . .
H H4B 0.1806 -0.019 0.8803 0.063 Uiso calc . . GR 1 . .
H H4C 0.116 -0.0252 0.8749 0.063 Uiso calc . . GR 1 . .
C C5 0.15196(18) 0.4416(5) 0.4581(6) 0.0401(10) Uani d . . . 1 . .
H H5A 0.1935 0.4501 0.4922 0.06 Uiso calc . . GR 1 . .
H H5B 0.1355 0.5404 0.4617 0.06 Uiso calc . . GR 1 . .
H H5C 0.1368 0.4023 0.3463 0.06 Uiso calc . . GR 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Fe1 0.0239(3) 0.0222(3) 0.0246(4) 0 0.0119(3) 0
Cl1 0.0310(6) 0.0222(5) 0.0319(6) 0 0.0121(6) 0
Cl2 0.0324(5) 0.0408(5) 0.0266(5) 0.0015(4) 0.0109(4) 0.0046(4)
Cl4 0.0219(5) 0.0728(8) 0.0634(7) 0.0083(5) 0.0119(5) 0.0077(6)
O1 0.058(2) 0.0220(18) 0.047(2) 0 0.036(2) 0
N1 0.0248(15) 0.0301(16) 0.0285(16) 0.0058(13) 0.0118(13) 0.0082(13)
N2 0.0234(15) 0.0328(16) 0.0329(17) 0.0060(13) 0.0146(14) 0.0120(14)
C1 0.0256(18) 0.0268(18) 0.0283(19) 0.0033(15) 0.0083(15) 0.0007(15)
C2 0.0180(16) 0.036(2) 0.0320(19) 0.0025(14) 0.0075(14) -0.0034(16)
C3 0.0246(18) 0.0312(19) 0.0314(19) 0.0004(15) 0.0124(16) -0.0006(15)
C4 0.037(2) 0.042(2) 0.045(2) 0.0150(18) 0.013(2) 0.017(2)
C5 0.035(2) 0.046(2) 0.044(2) -0.0022(19) 0.0195(19) 0.011(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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Fe1 Cl1 . 2.3093(14) ?
Fe1 Cl2 2_556 2.3478(9) ?
Fe1 Cl2 . 2.3478(9) ?
Fe1 O1 . 2.068(4) ?
Fe1 N1 . 2.158(3) ?
Fe1 N1 2_556 2.158(3) ?
Cl4 C2 . 1.717(4) ?
O1 H1 . 1.02(6) ?
N1 N2 . 1.366(4) ?
N1 C1 . 1.345(5) ?
N2 H2 . 0.89(5) ?
N2 C3 . 1.339(5) ?
C1 C2 . 1.402(5) ?
C1 C4 . 1.490(5) ?
C2 C3 . 1.366(5) ?
C3 C5 . 1.484(5) ?
C4 H4A . 0.96 ?
C4 H4B . 0.96 ?
C4 H4C . 0.96 ?
C5 H5A . 0.96 ?
C5 H5B . 0.96 ?
C5 H5C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl1 Fe1 Cl2 . . 91.09(3) ?
Cl1 Fe1 Cl2 . 2_556 91.09(3) ?
Cl2 Fe1 Cl2 2_556 . 177.83(6) ?
O1 Fe1 Cl1 . . 180.0 ?
O1 Fe1 Cl2 . 2_556 88.91(3) ?
O1 Fe1 Cl2 . . 88.91(3) ?
O1 Fe1 N1 . 2_556 89.37(9) ?
O1 Fe1 N1 . . 89.37(9) ?
N1 Fe1 Cl1 . . 90.63(9) ?
N1 Fe1 Cl1 2_556 . 90.63(9) ?
N1 Fe1 Cl2 2_556 2_556 91.94(9) ?
N1 Fe1 Cl2 . 2_556 88.04(9) ?
N1 Fe1 Cl2 2_556 . 88.04(9) ?
N1 Fe1 Cl2 . . 91.94(9) ?
N1 Fe1 N1 2_556 . 178.74(17) ?
Fe1 O1 H1 . . 118.(3) ?
N2 N1 Fe1 . . 116.4(2) ?
C1 N1 Fe1 . . 136.2(2) ?
C1 N1 N2 . . 105.5(3) ?
N1 N2 H2 . . 118.(3) ?
C3 N2 H2 . . 129.(3) ?
C3 N2 N1 . . 112.8(3) ?
N1 C1 C2 . . 108.2(3) ?
N1 C1 C4 . . 124.0(3) ?
C2 C1 C4 . . 127.8(3) ?
C1 C2 Cl4 . . 125.6(3) ?
C3 C2 Cl4 . . 126.0(3) ?
C3 C2 C1 . . 108.4(3) ?
N2 C3 C2 . . 105.1(3) ?
N2 C3 C5 . . 123.3(3) ?
C2 C3 C5 . . 131.6(4) ?
C1 C4 H4A . . 109.5 ?
C1 C4 H4B . . 109.5 ?
C1 C4 H4C . . 109.5 ?
H4A C4 H4B . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C3 C5 H5A . . 109.5 ?
C3 C5 H5B . . 109.5 ?
C3 C5 H5C . . 109.5 ?
H5A C5 H5B . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Fe1 N1 N2 C3 . . . . 166.6(3) ?
Fe1 N1 C1 C2 . . . . -162.5(3) ?
Fe1 N1 C1 C4 . . . . 20.2(6) ?
Cl4 C2 C3 N2 . . . . 179.9(3) ?
Cl4 C2 C3 C5 . . . . 0.4(7) ?
N1 N2 C3 C2 . . . . 0.0(4) ?
N1 N2 C3 C5 . . . . 179.6(4) ?
N1 C1 C2 Cl4 . . . . 180.0(3) ?
N1 C1 C2 C3 . . . . -0.4(5) ?
N2 N1 C1 C2 . . . . 0.4(4) ?
N2 N1 C1 C4 . . . . -176.9(4) ?
C1 N1 N2 C3 . . . . -0.3(4) ?
C1 C2 C3 N2 . . . . 0.2(4) ?
C1 C2 C3 C5 . . . . -179.3(4) ?
C4 C1 C2 Cl4 . . . . -2.9(6) ?
C4 C1 C2 C3 . . . . 176.7(4) ?

_shelx_res_file                  
;

    ad_a.res created by SHELXL-2014/7

TITL ad_a.res in P-1 New: C2/c
REM #####
CELL 0.71073 24.487 8.7651 8.5302 90 110.281 90
ZERR 4 0.003 0.001 0.001 0 0.003 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H Cl Fe N O
UNIT 40 64 20 4 16 4

L.S. 100
PLAN  20
SIZE 0.466 0.617 0.699
LIST 4
BOND $H
HTAB
CONF
MORE -1
fmap 2
acta
TWIN 0.999 0 1.999 0 -1 0 0.001 0 -0.999 2
REM <olex2.extras>
REM <HklSrc "%.\\ad_a.hkl">
REM </olex2.extras>

WGHT    0.009900    7.641800
BASF   0.14944
FVAR       0.30618
FE1   4    0.000000    0.221125    0.750000    10.50000    0.02395    0.02221 =
         0.02456    0.00000    0.01191    0.00000
H1    2   -0.009915   -0.068934    0.841969    11.00000    0.08594
CL1   3    0.000000    0.484585    0.750000    10.50000    0.03099    0.02220 =
         0.03193    0.00000    0.01212    0.00000
CL2   3    0.052458    0.216052    1.038368    11.00000    0.03240    0.04080 =
         0.02663    0.00464    0.01087    0.00149
H2    2    0.049670    0.368329    0.512719    11.00000    0.04179
CL4   3    0.242801    0.204668    0.741264    11.00000    0.02188    0.07278 =
         0.06338    0.00765    0.01186    0.00835
O1    6    0.000000   -0.014833    0.750000    10.50000    0.05802    0.02202 =
         0.04724    0.00000    0.03614    0.00000
N1    5    0.078947    0.218416    0.691390    11.00000    0.02483    0.03005 =
         0.02846    0.00823    0.01179    0.00584
N2    5    0.082572    0.322806    0.576426    11.00000    0.02336    0.03279 =
         0.03290    0.01197    0.01458    0.00596
C1    1    0.133207    0.163312    0.763133    11.00000    0.02556    0.02679 =
         0.02827    0.00074    0.00826    0.00332
C2    1    0.169497    0.236600    0.690678    11.00000    0.01795    0.03604 =
         0.03198   -0.00344    0.00745    0.00248
C3    1    0.136607    0.336590    0.572848    11.00000    0.02459    0.03121 =
         0.03143   -0.00055    0.01239    0.00038
C4    1    0.149030    0.039868    0.891159    11.00000    0.03708    0.04234 =
         0.04543    0.01715    0.01332    0.01504
AFIX 137
H4A   2    0.160713    0.084262    1.000738    11.00000   -1.50000
H4B   2    0.180594   -0.019000    0.880340    11.00000   -1.50000
H4C   2    0.115978   -0.025190    0.874883    11.00000   -1.50000
AFIX   0
C5    1    0.151964    0.441611    0.458134    11.00000    0.03506    0.04555 =
         0.04417    0.01060    0.01946   -0.00222
AFIX 137
H5A   2    0.193544    0.450122    0.492188    11.00000   -1.50000
H5B   2    0.135500    0.540388    0.461712    11.00000   -1.50000
H5C   2    0.136783    0.402272    0.346277    11.00000   -1.50000
AFIX   0
HKLF 4 1 0 1 -2 0 1 0 1 0 0

REM  ad_a.res in P-1 New: C2/c
REM R1 =  0.0428 for    1758 Fo > 4sig(Fo)  and  0.0503 for all    1975 data
REM    108 parameters refined using      0 restraints

END

WGHT      0.0100      7.5998

REM Instructions for potential hydrogen bonds
EQIV $1 -x, -y, -z+2
HTAB O1 Cl2_$1
EQIV $2 -x, -y+1, -z+1
HTAB N2 Cl1_$2
EQIV $3 -x, y, -z+3/2
HTAB N2 Cl2_$3

REM Highest difference peak  0.341,  deepest hole -0.385,  1-sigma level  0.086
Q1    1  -0.0002  0.4377  0.4962  11.00000  0.05    0.34
Q2    1   0.0544  0.5173  0.5390  11.00000  0.05    0.34
Q3    1   0.0428  0.2179  0.7256  11.00000  0.05    0.33
Q4    1   0.1542  0.2169  0.7289  11.00000  0.05    0.32
Q5    1   0.1922  0.2094  0.7118  11.00000  0.05    0.31
Q6    1   0.1559 -0.0808  0.8435  11.00000  0.05    0.30
Q7    1   0.1837  0.5416  0.5144  11.00000  0.05    0.30
Q8    1   0.2107  0.0526  0.9551  11.00000  0.05    0.29
Q9    1   0.0507  0.2309  0.8523  11.00000  0.05    0.29
Q10   1   0.0369  0.4622  0.9073  11.00000  0.05    0.28
Q11   1   0.0037  0.2377  1.0137  11.00000  0.05    0.28
Q12   1   0.0596  0.4449  0.8262  11.00000  0.05    0.28
Q13   1   0.1720  0.4600  0.7045  11.00000  0.05    0.28
Q14   1   0.1076  0.2172  0.7351  11.00000  0.05    0.27
Q15   1   0.2500  0.2500  1.0000  10.50000  0.05    0.27
Q16   1   0.0811  0.2267  0.7756  11.00000  0.05    0.26
Q17   1   0.1328  0.0513  0.9312  11.00000  0.05    0.26
Q18   1   0.1538  0.6964  0.6039  11.00000  0.05    0.26
Q19   1   0.1791  0.2881  0.7301  11.00000  0.05    0.26
Q20   1   0.1859  0.4291  0.2712  11.00000  0.05    0.26
;
_shelx_res_checksum              91995
