# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_C1
_database_code_depnum_ccdc_archive 'CCDC 1855808'
_audit_update_record             
;
2018-07-13 deposited with the CCDC.
2018-08-24 downloaded from the CCDC.
;
# local name ms17006_refinalized
_audit_creation_date             2018-07-13
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
g.s.nichol@ed.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Cl Fe N2 O2'
_chemical_formula_sum            'C16 H16 Cl Fe N2 O2'
_chemical_formula_weight         359.61
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H17 Cl Fe N2 O2'
_chemical_oxdiff_usercomment     '@ 120 K EFP112'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   12.5989(3)
_cell_length_b                   7.39494(17)
_cell_length_c                   17.7897(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.536(3)
_cell_angle_gamma                90
_cell_volume                     1571.44(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10338
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      32.4980
_cell_measurement_theta_min      4.3470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.137
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.413
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             740
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 1 -20 0.1148
-16 3 15 0.1824
-4 0 25 0.1092
5 -1 20 0.1017
15 -2 -19 0.1893
-9 2 -16 0.1441
10 -2 14 0.1491
12 7 -12 0.1341
-10 9 7 0.1652
-1 10 -1 0.1571
-9 -9 9 0.1493
-17 -1 15 0.1808
-1 -10 3 0.1328
16 -3 -14 0.1836
-7 -7 -13 0.1459
-12 -5 -8 0.1441
-6 7 19 0.1382
7 7 13 0.1131
15 4 3 0.1546
9 5 -21 0.1482
-7 8 -9 0.1569
5 -8 11 0.1306
-2 -7 18 0.1155
12 7 -3 0.1224
9 9 1 0.1164
-3 10 10 0.1389

_exptl_crystal_recrystallization_method 
'The material was recrystallised from dichloromethane by slow evaporation'
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.217
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.0018 0.9939 -19.9793 0.9355 -0.2945 0.0163
-15.9963 3.0016 14.9880 -0.0502 -0.0165 0.9993
-3.9971 0.0063 24.9767 -0.8180 0.3080 0.4871
5.0018 -0.9939 19.9793 -0.9355 0.2945 -0.0163
14.9966 -2.0031 -18.9847 0.2220 -0.1149 -0.9759
-9.0006 1.9943 -15.9828 0.9086 -0.3184 0.2754
10.0004 -1.9947 13.9844 -0.8680 0.2902 -0.3459
12.0049 6.9951 -11.9990 -0.1099 -0.8338 -0.5261
-9.9920 8.9977 6.9881 -0.0757 -0.6828 0.7749
-0.9918 9.9959 -1.0081 -0.1157 -0.9118 0.2856
-9.0068 -8.9949 9.0028 0.1540 0.9649 0.3004
-16.9997 -0.9970 14.9922 0.0627 0.3509 0.9452
-1.0081 -9.9955 3.0069 0.1117 0.9451 -0.1686
15.9964 -3.0013 -13.9890 0.0116 0.0280 -0.9872
-7.0077 -7.0013 -12.9780 0.8914 0.5207 -0.0074
-12.0056 -5.0012 -7.9830 0.8434 0.4229 0.3353
-5.9921 7.0019 18.9767 -0.6469 -0.3845 0.6835
7.0077 7.0013 12.9780 -0.8914 -0.5207 0.0074
15.0043 4.0004 2.9879 -0.7412 -0.4053 -0.5600
9.0020 4.9932 -20.9872 0.3853 -0.7406 -0.5455
-6.9946 7.9940 -8.9962 0.4508 -0.7916 0.4176
4.9948 -7.9936 10.9949 -0.4547 0.8249 -0.3006
-2.0038 -6.9927 17.9895 -0.4876 0.8511 0.1340
12.0060 6.9975 -3.0080 -0.4572 -0.7304 -0.4176
9.0080 8.9975 0.9873 -0.5398 -0.8500 -0.1798
-2.9905 9.9986 9.9817 -0.4668 -0.7751 0.5111

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19409
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.888
_diffrn_reflns_theta_min         3.008
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  -4.00   1.00    5.00    --  -17.68 102.00  34.00   55
  2  ω    -12.00  93.00   1.00    5.00    --   19.09  77.00 -60.00  105
  3  ω    -12.00  93.00   1.00    5.00    --   19.09  77.00-150.00  105
  4  ω     -3.00  92.00   1.00    5.00    --   19.09  38.00-150.00   95
  5  ω    -20.00  59.00   1.00    5.00    --   19.09 -99.00  30.00   79
  6  ω     -3.00  92.00   1.00    5.00    --   19.09  38.00 120.00   95
  7  ω   -104.00 -57.00   1.00    5.00    --  -17.68-178.00 150.00   47
  8  ω    -51.00  46.00   1.00    5.00    --   19.09 -57.00-180.00   97
  9  ω     35.00  83.00   1.00    5.00    --   19.09 178.00-180.00   48
 10  ω    -20.00  59.00   1.00    5.00    --   19.09 -99.00-180.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0366194000
_diffrn_orient_matrix_UB_12      -0.0190969000
_diffrn_orient_matrix_UB_13      -0.0386078000
_diffrn_orient_matrix_UB_21      -0.0051627000
_diffrn_orient_matrix_UB_22      -0.0905690000
_diffrn_orient_matrix_UB_23      0.0115280000
_diffrn_orient_matrix_UB_31      -0.0464408000
_diffrn_orient_matrix_UB_32      0.0251827000
_diffrn_orient_matrix_UB_33      0.0120646000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2618
_reflns_number_total             2808
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0263P)²+1.5933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0690
_refine_special_details          
;
#===============================================================================
The Following Improvement and Query ALERTS were generated - (Acta-Mode) <<<
#===============================================================================
     Format: alert-number_ALERT_alert-type_alert-level text

094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.25 Report

Not significant

#===============================================================================
232_ALERT_2_G Hirshfeld Test Diff (M-X) Fe1      --N1        .        5.8 s.u.
910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        121 Note
978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

Not significant
#===============================================================================
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.250000 0.73639(3) 0.500000 0.01520(7) Uani 1 2 d S T P . .
Cl1 Cl 0.250000 0.42925(6) 0.500000 0.02916(11) Uani 1 2 d S T P . .
O1 O 0.18161(7) 0.86130(14) 0.40515(5) 0.02237(18) Uani 1 1 d . . . . .
N1 N 0.40454(8) 0.74275(13) 0.47733(6) 0.01605(17) Uani 1 1 d . . . . .
C1 C 0.42469(9) 0.88550(15) 0.63808(6) 0.01618(19) Uani 1 1 d . . . . .
C2 C 0.44918(10) 0.95029(17) 0.71604(7) 0.0198(2) Uani 1 1 d . . . . .
H2 H 0.389733 0.980455 0.735844 0.024 Uiso 1 1 calc R . . . .
C3 C 0.55894(10) 0.97065(17) 0.76430(7) 0.0204(2) Uani 1 1 d . . . . .
H3 H 0.573976 1.011911 0.817243 0.025 Uiso 1 1 calc R . . . .
C4 C 0.64765(10) 0.93123(18) 0.73602(7) 0.0225(2) Uani 1 1 d . . . . .
H4 H 0.722761 0.944468 0.769598 0.027 Uiso 1 1 calc R . . . .
C5 C 0.62545(10) 0.87280(17) 0.65882(7) 0.0204(2) Uani 1 1 d . . . . .
H5 H 0.685862 0.848616 0.639176 0.024 Uiso 1 1 calc R . . . .
C6 C 0.51464(9) 0.84849(15) 0.60873(6) 0.01548(19) Uani 1 1 d . . . . .
C7 C 0.49871(9) 0.78669(15) 0.52873(7) 0.01632(19) Uani 1 1 d . . . . .
H7 H 0.563559 0.777696 0.512639 0.020 Uiso 1 1 calc R . . . .
C8 C 0.40672(10) 0.67961(18) 0.39961(7) 0.0209(2) Uani 1 1 d . . . . .
H8A H 0.390989 0.549597 0.394637 0.031 Uiso 1 1 calc GR . . . .
H8B H 0.480802 0.702634 0.394643 0.031 Uiso 1 1 calc GR . . . .
H8C H 0.349830 0.744461 0.357670 0.031 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 Cl1 2.2713(5) . ?
Fe1 O1 1.8758(9) . ?
Fe1 O1 1.8757(9) 2_556 ?
Fe1 N1 2.1106(10) 2_556 ?
Fe1 N1 2.1106(10) . ?
O1 C1 1.3275(13) 2_556 ?
N1 C7 1.2882(15) . ?
N1 C8 1.4678(14) . ?
C1 C2 1.4058(15) . ?
C1 C6 1.4171(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.3846(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.3946(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3809(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.4086(16) . ?
C6 C7 1.4468(15) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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 Cl1 119.50(3) . . ?
O1 Fe1 Cl1 119.50(3) 2_556 . ?
O1 Fe1 O1 121.00(6) 2_556 . ?
O1 Fe1 N1 90.29(4) 2_556 2_556 ?
O1 Fe1 N1 88.46(4) . 2_556 ?
O1 Fe1 N1 90.28(4) . . ?
O1 Fe1 N1 88.46(4) 2_556 . ?
N1 Fe1 Cl1 91.28(3) 2_556 . ?
N1 Fe1 Cl1 91.28(3) . . ?
N1 Fe1 N1 177.44(5) . 2_556 ?
C1 O1 Fe1 132.67(7) 2_556 . ?
C7 N1 Fe1 124.57(8) . . ?
C7 N1 C8 117.38(10) . . ?
C8 N1 Fe1 117.88(7) . . ?
O1 C1 C2 118.82(10) 2_556 . ?
O1 C1 C6 122.56(10) 2_556 . ?
C2 C1 C6 118.62(10) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.76(11) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.70(11) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.48(11) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.04(11) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 123.12(10) . . ?
C5 C6 C1 119.35(10) . . ?
C5 C6 C7 117.53(10) . . ?
N1 C7 C6 125.90(10) . . ?
N1 C7 H7 117.1 . . ?
C6 C7 H7 117.1 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 N1 C7 C6 -3.65(17) . . . . ?
Cl1 Fe1 O1 C1 71.88(12) . . . 2_556 ?
O1 Fe1 O1 C1 -108.12(12) 2_556 . . 2_556 ?
O1 C1 C2 C3 177.40(11) 2_556 . . . ?
O1 C1 C6 C5 -178.28(11) 2_556 . . . ?
O1 C1 C6 C7 1.95(18) 2_556 . . . ?
N1 Fe1 O1 C1 -18.71(11) 2_556 . . 2_556 ?
N1 Fe1 O1 C1 163.51(11) . . . 2_556 ?
C1 C2 C3 C4 1.48(19) . . . . ?
C1 C6 C7 N1 -6.48(19) . . . . ?
C2 C1 C6 C5 1.69(17) . . . . ?
C2 C1 C6 C7 -178.07(11) . . . . ?
C2 C3 C4 C5 0.56(19) . . . . ?
C3 C4 C5 C6 -1.44(19) . . . . ?
C4 C5 C6 C1 0.30(18) . . . . ?
C4 C5 C6 C7 -179.92(11) . . . . ?
C5 C6 C7 N1 173.75(11) . . . . ?
C6 C1 C2 C3 -2.58(18) . . . . ?
C8 N1 C7 C6 -178.77(11) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.342
_oxdiff_exptl_absorpt_empirical_full_min 0.825
####################################################################### 
# 
# 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_C3
_database_code_depnum_ccdc_archive 'CCDC 1855810'
_audit_update_record             
;
2018-07-13 deposited with the CCDC.
2018-08-24 downloaded from the CCDC.
;
# local name ms17004_refinalized
_audit_creation_date             2018-07-13
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
g.s.nichol@ed.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Cl3 Fe N2 O2'
_chemical_formula_sum            'C16 H14 Cl3 Fe N2 O2'
_chemical_formula_weight         428.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H14 Cl3 Fe N2 O2'
_chemical_oxdiff_usercomment     '@ 120 K EFP88'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_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                   23.1547(3)
_cell_length_b                   12.00241(14)
_cell_length_c                   12.99462(16)
_cell_angle_alpha                90
_cell_angle_beta                 102.4166(12)
_cell_angle_gamma                90
_cell_volume                     3526.89(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13515
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      75.8080
_cell_measurement_theta_min      3.8950
_shelx_estimated_absorpt_T_max   0.606
_shelx_estimated_absorpt_T_min   0.427
_exptl_absorpt_coefficient_mu    11.142
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1736
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
13 4 1 0.0397
1 2 -8 0.0368
-13 -4 0 0.0496
-2 -2 8 0.0351
10 5 -4 0.0402
7 -7 -2 0.0262
-7 -6 3 0.0484
-8 6 3 0.0214

_exptl_crystal_recrystallization_method 
'The material was recrystallised from dichloromethane by slow evaporation'
_exptl_crystal_size_max          0.092
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
12.7909 3.5634 0.5616 0.1439 0.5954 0.7905
0.8109 1.6815 -8.1308 -0.1969 -0.8272 0.5263
-12.9123 -3.7012 0.0166 -0.1305 -0.5392 -0.8320
-1.9652 -2.0110 8.1243 0.1850 0.7781 -0.6002
9.7441 5.2836 -4.0219 0.1894 -0.0470 0.9808
7.4561 -6.6591 -2.1803 -0.9725 0.2327 -0.0090
-7.4867 -6.3687 3.2838 -0.3866 0.0941 -0.9174
-8.3167 6.3319 2.5238 0.9704 -0.2320 -0.0677

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27812
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.025
_diffrn_reflns_theta_min         3.910
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  29.00   1.00    5.00    --  -41.92  65.00   1.00   99
  2  ω   -115.00 -19.00   1.00    5.00    --  -41.92 -38.00  90.00   96
  3  ω    -64.00  31.00   1.00    5.00    --  -41.92  38.00 -90.00   95
  4  ω     57.00 129.00   1.00    5.00    --   41.92 178.00-180.00   72
  5  ω     57.00 129.00   1.00    5.00    --   41.92 178.00 -60.00   72
  6  ω     36.00 135.00   1.00   20.00    --  111.00 -30.00 -90.00   99
  7  ω     41.00 139.00   1.00   20.00    --  111.00 -61.00 -60.00   98
  8  ω     87.00 178.00   1.00   20.00    --  111.00  30.00-180.00   91
  9  ω     94.00 178.00   1.00   20.00    --  111.00 125.00 -90.00   84
 10  ω     30.00 109.00   1.00   20.00    --  111.00 -94.00 -30.00   79
 11  ω     30.00 109.00   1.00   20.00    --  111.00 -94.00  60.00   79
 12  ω     30.00 109.00   1.00   20.00    --  111.00 -94.00 120.00   79
 13  ω     30.00 109.00   1.00   20.00    --  111.00 -94.00 -60.00   79
 14  ω     39.00 121.00   1.00   20.00    --  111.00-125.00  90.00   82
 15  ω     83.00 178.00   1.00   20.00    --  111.00  61.00-120.00   95
 16  ω     87.00 178.00   1.00   20.00    --  111.00  30.00-120.00   91
 17  ω     39.00 121.00   1.00   20.00    --  111.00-125.00 -60.00   82
 18  ω     87.00 178.00   1.00   20.00    --  111.00  45.00  60.00   91
 19  ω     94.00 178.00   1.00   20.00    --  111.00 125.00-150.00   84
 20  ω     39.00 121.00   1.00   20.00    --  111.00-125.00 -90.00   82
 21  ω     66.00 178.00   1.00   20.00    --  111.00  15.00-150.00  112
 22  ω     40.00 135.00   1.00   20.00    --  111.00 -45.00-180.00   95
 23  ω     39.00 121.00   1.00   20.00    --  111.00-125.00-150.00   82
 24  ω     94.00 178.00   1.00   20.00    --  111.00 125.00-120.00   84
 25  ω     30.00 109.00   1.00   20.00    --  111.00 -94.00-150.00   79
 26  ω     39.00 121.00   1.00   20.00    --  111.00-125.00 120.00   82
 27  ω     40.00  84.00   1.00   20.00    --  111.00-125.00   0.00   44
 28  ω    114.00 158.00   1.00   20.00    --  111.00 125.00 -30.00   44
 29  ω    105.00 150.00   1.00   20.00    --  111.00 125.00 120.00   45
 30  ω    102.00 131.00   1.00   20.00    --  111.00 -30.00-180.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0208322000
_diffrn_orient_matrix_UB_12      0.1081463000
_diffrn_orient_matrix_UB_13      0.0445053000
_diffrn_orient_matrix_UB_21      0.0466111000
_diffrn_orient_matrix_UB_22      -0.0164659000
_diffrn_orient_matrix_UB_23      0.1029783000
_diffrn_orient_matrix_UB_31      0.0451477000
_diffrn_orient_matrix_UB_32      0.0670778000
_diffrn_orient_matrix_UB_33      -0.0463543000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3446
_reflns_number_total             3677
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3677
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0790P)²+1.6030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1092
_refine_special_details          
;
#===============================================================================
The Following Improvement and Query ALERTS were generated - (Acta-Mode) <<<
#===============================================================================
     Format: alert-number_ALERT_alert-type_alert-level text

411_ALERT_2_C Short Inter H...H Contact H13      ..H13       .       2.14 Ang.

Not significant

#===============================================================================
232_ALERT_2_G Hirshfeld Test Diff (M-X) Fe1      --N2        .        5.3 s.u.
380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C16 Check
912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         15 Note
978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

Not significant

#===============================================================================
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C11(H11), C12(H12), C13(H13), C15(H15)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.33472(2) 0.90086(3) 0.30749(2) 0.01799(12) Uani 1 1 d . . . . .
Cl1 Cl 0.24197(2) 0.89672(5) 0.33488(4) 0.03027(15) Uani 1 1 d . . . . .
Cl2 Cl 0.41390(3) 0.54937(5) 0.26146(6) 0.04334(18) Uani 1 1 d . . . . .
Cl3 Cl 0.42975(3) 1.24824(4) 0.29819(4) 0.03156(15) Uani 1 1 d . . . . .
O1 O 0.36290(7) 0.77070(13) 0.25605(13) 0.0256(3) Uani 1 1 d . . . . .
O2 O 0.38158(7) 1.03069(13) 0.33512(12) 0.0232(3) Uani 1 1 d . . . . .
N1 N 0.30557(8) 0.95450(15) 0.15183(14) 0.0206(3) Uani 1 1 d . . . . .
N2 N 0.37175(8) 0.84849(15) 0.46213(14) 0.0217(3) Uani 1 1 d . . . . .
C1 C 0.35586(10) 0.72683(18) 0.16095(18) 0.0241(4) Uani 1 1 d . . . . .
C2 C 0.37782(11) 0.6190(2) 0.1491(2) 0.0306(5) Uani 1 1 d . . . . .
C3 C 0.37142(12) 0.5696(2) 0.0515(2) 0.0372(6) Uani 1 1 d . . . . .
H3 H 0.386516 0.496640 0.046314 0.045 Uiso 1 1 calc R . . . .
C4 C 0.34334(12) 0.6246(2) -0.0390(2) 0.0357(6) Uani 1 1 d . . . . .
H4 H 0.338986 0.589839 -0.105975 0.043 Uiso 1 1 calc R . . . .
C5 C 0.32168(10) 0.7308(2) -0.03075(19) 0.0297(5) Uani 1 1 d . . . . .
H5 H 0.302530 0.769261 -0.092606 0.036 Uiso 1 1 calc R . . . .
C6 C 0.32763(9) 0.78282(18) 0.06827(17) 0.0235(4) Uani 1 1 d . . . . .
C7 C 0.30430(9) 0.89483(18) 0.06932(17) 0.0226(4) Uani 1 1 d . . . . .
H7 H 0.286542 0.926864 0.003240 0.027 Uiso 1 1 calc R . . . .
C8 C 0.27932(10) 1.0667(2) 0.13731(18) 0.0267(4) Uani 1 1 d . . . . .
H8A H 0.246079 1.071134 0.172794 0.040 Uiso 1 1 calc GR . . . .
H8B H 0.265190 1.081503 0.061925 0.040 Uiso 1 1 calc GR . . . .
H8C H 0.309231 1.122197 0.167571 0.040 Uiso 1 1 calc GR . . . .
C9 C 0.41584(9) 1.07225(17) 0.42090(16) 0.0190(4) Uani 1 1 d . . . . .
C10 C 0.44276(9) 1.17743(18) 0.41701(17) 0.0225(4) Uani 1 1 d . . . . .
C11 C 0.47769(10) 1.22625(19) 0.50531(19) 0.0265(4) Uani 1 1 d . . . . .
H11 H 0.494815 1.297350 0.499872 0.032 Uiso 1 1 calc R . . . .
C12 C 0.48785(10) 1.1717(2) 0.60198(19) 0.0286(5) Uani 1 1 d . . . . .
H12 H 0.511668 1.205390 0.662681 0.034 Uiso 1 1 calc R . . . .
C13 C 0.46306(10) 1.0686(2) 0.60882(18) 0.0263(4) Uani 1 1 d . . . . .
H13 H 0.470082 1.031209 0.674771 0.032 Uiso 1 1 calc R . . . .
C14 C 0.42741(9) 1.01735(18) 0.51972(16) 0.0206(4) Uani 1 1 d . . . . .
C15 C 0.40545(9) 0.90681(18) 0.53325(17) 0.0221(4) Uani 1 1 d . . . . .
H15 H 0.417082 0.874319 0.601226 0.026 Uiso 1 1 calc R . . . .
C16 C 0.35663(12) 0.73556(19) 0.49100(19) 0.0305(5) Uani 1 1 d . . . . .
H16A H 0.313718 0.729711 0.483602 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.376372 0.720302 0.564207 0.046 Uiso 1 1 calc GR . . . .
H16C H 0.369715 0.681304 0.444460 0.046 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 Cl1 2.2517(6) . ?
Fe1 O1 1.8711(16) . ?
Fe1 O2 1.8886(15) . ?
Fe1 N1 2.0916(18) . ?
Fe1 N2 2.1041(18) . ?
Cl2 C2 1.734(3) . ?
Cl3 C10 1.731(2) . ?
O1 C1 1.321(3) . ?
O2 C9 1.319(3) . ?
N1 C7 1.284(3) . ?
N1 C8 1.473(3) . ?
N2 C15 1.282(3) . ?
N2 C16 1.469(3) . ?
C1 C2 1.411(3) . ?
C1 C6 1.411(3) . ?
C2 C3 1.379(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.410(3) . ?
C6 C7 1.450(3) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.414(3) . ?
C9 C14 1.417(3) . ?
C10 C11 1.384(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.375(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.411(3) . ?
C14 C15 1.445(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 Cl1 117.12(5) . . ?
O1 Fe1 O2 121.78(7) . . ?
O1 Fe1 N1 88.64(7) . . ?
O1 Fe1 N2 89.43(7) . . ?
O2 Fe1 Cl1 121.11(5) . . ?
O2 Fe1 N1 89.00(7) . . ?
O2 Fe1 N2 88.02(7) . . ?
N1 Fe1 Cl1 92.25(5) . . ?
N1 Fe1 N2 174.92(7) . . ?
N2 Fe1 Cl1 92.81(5) . . ?
C1 O1 Fe1 133.22(15) . . ?
C9 O2 Fe1 133.56(14) . . ?
C7 N1 Fe1 125.48(15) . . ?
C7 N1 C8 117.92(18) . . ?
C8 N1 Fe1 116.34(13) . . ?
C15 N2 Fe1 125.83(15) . . ?
C15 N2 C16 117.48(18) . . ?
C16 N2 Fe1 116.68(14) . . ?
O1 C1 C2 119.5(2) . . ?
O1 C1 C6 123.4(2) . . ?
C2 C1 C6 117.1(2) . . ?
C1 C2 Cl2 118.0(2) . . ?
C3 C2 Cl2 120.3(2) . . ?
C3 C2 C1 121.7(3) . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.9(2) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 122.6(2) . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 C7 117.1(2) . . ?
N1 C7 C6 125.7(2) . . ?
N1 C7 H7 117.2 . . ?
C6 C7 H7 117.2 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C10 119.81(19) . . ?
O2 C9 C14 123.52(19) . . ?
C10 C9 C14 116.68(19) . . ?
C9 C10 Cl3 118.48(16) . . ?
C11 C10 Cl3 119.35(17) . . ?
C11 C10 C9 122.1(2) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.3(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C9 C14 C15 122.31(19) . . ?
C13 C14 C9 120.3(2) . . ?
C13 C14 C15 117.4(2) . . ?
N2 C15 C14 126.1(2) . . ?
N2 C15 H15 116.9 . . ?
C14 C15 H15 116.9 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O1 C1 C2 -172.66(16) . . . . ?
Fe1 O1 C1 C6 8.0(3) . . . . ?
Fe1 O2 C9 C10 -175.93(15) . . . . ?
Fe1 O2 C9 C14 3.5(3) . . . . ?
Fe1 N1 C7 C6 -5.8(3) . . . . ?
Fe1 N2 C15 C14 -3.8(3) . . . . ?
Cl1 Fe1 O1 C1 80.9(2) . . . . ?
Cl1 Fe1 O2 C9 84.41(19) . . . . ?
Cl2 C2 C3 C4 -179.26(19) . . . . ?
Cl3 C10 C11 C12 178.83(17) . . . . ?
O1 Fe1 O2 C9 -95.8(2) . . . . ?
O1 C1 C2 Cl2 -0.5(3) . . . . ?
O1 C1 C2 C3 179.8(2) . . . . ?
O1 C1 C6 C5 180.0(2) . . . . ?
O1 C1 C6 C7 0.7(3) . . . . ?
O2 Fe1 O1 C1 -99.0(2) . . . . ?
O2 C9 C10 Cl3 -0.2(3) . . . . ?
O2 C9 C10 C11 178.09(19) . . . . ?
O2 C9 C14 C13 -177.99(19) . . . . ?
O2 C9 C14 C15 4.2(3) . . . . ?
N1 Fe1 O1 C1 -11.0(2) . . . . ?
N1 Fe1 O2 C9 176.44(19) . . . . ?
N2 Fe1 O1 C1 173.7(2) . . . . ?
N2 Fe1 O2 C9 -7.68(19) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C1 C6 C7 N1 -1.0(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C6 C7 -178.59(19) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 C7 179.2(2) . . . . ?
C5 C6 C7 N1 179.7(2) . . . . ?
C6 C1 C2 Cl2 178.85(16) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C8 N1 C7 C6 -179.74(19) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C9 C14 C15 N2 -3.5(3) . . . . ?
C10 C9 C14 C13 1.5(3) . . . . ?
C10 C9 C14 C15 -176.39(19) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C9 -0.7(3) . . . . ?
C12 C13 C14 C15 177.2(2) . . . . ?
C13 C14 C15 N2 178.6(2) . . . . ?
C14 C9 C10 Cl3 -179.71(15) . . . . ?
C14 C9 C10 C11 -1.4(3) . . . . ?
C16 N2 C15 C14 177.3(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id EFP88
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.396
_oxdiff_exptl_absorpt_empirical_full_min 0.625
####################################################################### 
# 
# 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_C2
_database_code_depnum_ccdc_archive 'CCDC 1855809'
_audit_update_record             
;
2018-07-13 deposited with the CCDC.
2018-08-24 downloaded from the CCDC.
;
# local name ms18002_refinalized_tw
_audit_creation_date             2018-07-13
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
g.s.nichol@ed.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C24 H32 Cl Fe N2 O2), C7 H8'
_chemical_formula_sum            'C55 H72 Cl2 Fe2 N4 O4'
_chemical_formula_weight         1035.76
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H32 Cl Fe N2 O2'
_chemical_oxdiff_usercomment     '@ 120 K EFP213'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8856(3)
_cell_length_b                   24.3385(7)
_cell_length_c                   19.8618(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.003(3)
_cell_angle_gamma                90
_cell_volume                     5261.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7950
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      75.7930
_cell_measurement_theta_min      4.8330
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.179
_exptl_absorpt_coefficient_mu    5.731
_exptl_absorpt_correction_T_max  0.4716
_exptl_absorpt_correction_T_min  0.2522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1197 before and 0.0935 after correction. The Ratio of minimum to maximum transmission is 0.5348. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent dark red'
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2192
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 -5 0.0783
0 -2 5 0.0783
-5 1 -5 0.1125
3 -2 5 0.1459
0 -1 0 0.0084
0 1 0 0.0084

_exptl_crystal_recrystallization_method 
'The material was recrystallised from toluene by slow evaporation'
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.017
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0032 1.9980 -4.9977 0.0584 -0.3897 0.1049
0.0032 -1.9980 4.9977 -0.0584 0.3897 -0.1049
-5.0009 0.9893 -4.9977 0.0665 -0.5660 -0.5834
3.0019 -1.9924 4.9976 -0.1004 0.5008 0.3027
0.0002 -0.9994 -0.0002 -0.0620 0.0088 -0.0089
-0.0002 0.9994 0.0002 0.0620 -0.0088 0.0089

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1073
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            10913
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.021
_diffrn_reflns_theta_min         3.632
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  31.00   1.00    5.00    --  -41.67  38.00 -30.00   95
  2  ω   -114.00 -19.00   1.00    5.00    --  -41.67 -38.00-180.00   95
  3  ω   -127.00 -34.00   1.00    5.00    --  -41.67 178.00  30.00   93
  4  ω     30.00 109.00   1.00   20.00    --  111.00 -94.00 120.00   79
  5  ω     37.00 142.00   1.00   20.00    --  111.00 -77.00-180.00  105
  6  ω     39.00 121.00   1.00   20.00    --  111.00-125.00 -60.00   82
  7  ω     36.00 135.00   1.00   20.00    --  111.00 -30.00 120.00   99
  8  ω     39.00 121.00   1.00   20.00    --  111.00-125.00-120.00   82
  9  ω     66.00 178.00   1.00   20.00    --  111.00  15.00  60.00  112
 10  ω     30.00 109.00   1.00   20.00    --  111.00 -94.00 -30.00   79
 11  ω     36.00 135.00   1.00   20.00    --  111.00 -30.00-120.00   99
 12  ω     93.00 135.00   1.00   20.00    --  111.00 -45.00 -60.00   42
 13  ω     69.00  98.00   1.00   20.00    --  111.00-118.00 128.00   29
 14  ω     34.00 102.00   1.00   20.00    --  111.00 -94.00  30.00   68
 15  ω     31.00  74.00   1.00   20.00    --  111.00 -94.00  60.00   43
 16  ω     88.00 142.00   1.00   20.00    --  111.00  30.00 120.00   54
 17  ω     45.00  80.00   1.00   20.00    --  111.00 -94.00 -60.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0141350000
_diffrn_orient_matrix_UB_12      0.0620140000
_diffrn_orient_matrix_UB_13      0.0131211000
_diffrn_orient_matrix_UB_21      0.0370425000
_diffrn_orient_matrix_UB_22      -0.0088237000
_diffrn_orient_matrix_UB_23      0.0744324000
_diffrn_orient_matrix_UB_31      0.1359277000
_diffrn_orient_matrix_UB_32      0.0089194000
_diffrn_orient_matrix_UB_33      -0.0175151000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7797
_reflns_number_total             10913
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.076
_refine_diff_density_min         -0.905
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         10913
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0969
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1005P)²+21.7650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2401
_refine_ls_wR_factor_ref         0.2617
_refine_special_details          
;
The TwinRotMat routine of PLATON was used to identify minor twinning and produce a reflection file in HKLF 5 format.  The twin scale factor is 0.137(4).



#===============================================================================
The Following Improvement and Query ALERTS were generated - (Acta-Mode) <<<
#===============================================================================
     Format: alert-number_ALERT_alert-type_alert-level text

084_ALERT_3_C High wR2 Value (i.e. > 0.25) ...................       0.26 Report

Twinned

341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.01035 Ang.
906_ALERT_3_C Large K Value in the Analysis of Variance ......      6.314 Check
906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.403 Check

Noted

#===============================================================================
072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.10 Report
083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      21.76 Why ?
870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         84 Note

Noted
#===============================================================================
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.863(4)
 0.137(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C15(H15), C16(H16), C17(H17), C19(H19),
 C27(H27), C28(H28), C29(H29), C31(H31), C39(H39), C40(H40), C41(H41), C43(H43),
  C51(H51), C52(H52), C53(H53), C54(H54), C55(H55)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,
 H24B,H24C), C32(H32A,H32B,H32C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C),
 C36(H36A,H36B,H36C), C44(H44A,H44B,H44C), C46(H46A,H46B,H46C), C47(H47A,H47B,
 H47C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.86170(9) 0.76910(4) 0.36521(5) 0.0238(2) Uani 1 1 d . . . . .
Cl1 Cl 0.67041(15) 0.79250(7) 0.39453(8) 0.0353(4) Uani 1 1 d . . . . .
O1 O 0.9570(4) 0.82531(19) 0.3276(2) 0.0295(9) Uani 1 1 d . . . . .
O2 O 0.9176(4) 0.69715(18) 0.3817(2) 0.0265(9) Uani 1 1 d . . . . .
N1 N 0.9386(5) 0.7908(2) 0.4594(3) 0.0302(12) Uani 1 1 d . . . . .
N2 N 0.8170(5) 0.7427(2) 0.2667(3) 0.0271(11) Uani 1 1 d . . . . .
C1 C 1.0490(6) 0.8566(3) 0.3486(3) 0.0269(12) Uani 1 1 d . . . . .
C2 C 1.1055(6) 0.8941(3) 0.3021(3) 0.0281(13) Uani 1 1 d . . . . .
C3 C 1.2058(6) 0.9245(3) 0.3268(4) 0.0342(15) Uani 1 1 d . . . . .
H3 H 1.246035 0.948893 0.296997 0.041 Uiso 1 1 calc R . . . .
C4 C 1.2491(7) 0.9208(3) 0.3929(4) 0.0378(16) Uani 1 1 d . . . . .
H4 H 1.317892 0.942188 0.407011 0.045 Uiso 1 1 calc R . . . .
C5 C 1.1936(6) 0.8866(3) 0.4377(4) 0.0346(15) Uani 1 1 d . . . . .
H5 H 1.222932 0.884867 0.483032 0.042 Uiso 1 1 calc R . . . .
C6 C 1.0931(6) 0.8539(3) 0.4169(3) 0.0290(13) Uani 1 1 d . . . . .
C7 C 1.0323(6) 0.8231(3) 0.4678(3) 0.0300(14) Uani 1 1 d . . . . .
H7 H 1.063904 0.826749 0.512517 0.036 Uiso 1 1 calc R . . . .
C8 C 0.8903(7) 0.7645(3) 0.5201(3) 0.0355(15) Uani 1 1 d . . . . .
H8A H 0.801989 0.771779 0.522939 0.053 Uiso 1 1 calc GR . . . .
H8B H 0.932585 0.779316 0.560043 0.053 Uiso 1 1 calc GR . . . .
H8C H 0.904061 0.724727 0.517662 0.053 Uiso 1 1 calc GR . . . .
C9 C 1.0567(7) 0.9003(3) 0.2300(3) 0.0313(14) Uani 1 1 d . . . . .
C10 C 0.9215(7) 0.9194(3) 0.2318(4) 0.0381(16) Uani 1 1 d . . . . .
H10A H 0.875044 0.895055 0.261287 0.057 Uiso 1 1 calc GR . . . .
H10B H 0.885734 0.918297 0.186246 0.057 Uiso 1 1 calc GR . . . .
H10C H 0.917979 0.957104 0.249153 0.057 Uiso 1 1 calc GR . . . .
C11 C 1.0644(7) 0.8448(3) 0.1923(4) 0.0368(15) Uani 1 1 d . . . . .
H11A H 1.150451 0.833218 0.190171 0.055 Uiso 1 1 calc GR . . . .
H11B H 1.030698 0.849148 0.146539 0.055 Uiso 1 1 calc GR . . . .
H11C H 1.017014 0.817038 0.216319 0.055 Uiso 1 1 calc GR . . . .
C12 C 1.1294(8) 0.9425(3) 0.1900(4) 0.0436(18) Uani 1 1 d . . . . .
H12A H 1.134233 0.977034 0.215329 0.065 Uiso 1 1 calc GR . . . .
H12B H 1.088157 0.949001 0.146516 0.065 Uiso 1 1 calc GR . . . .
H12C H 1.212521 0.928534 0.182621 0.065 Uiso 1 1 calc GR . . . .
C13 C 0.9657(5) 0.6585(2) 0.3417(3) 0.0235(12) Uani 1 1 d . . . . .
C14 C 1.0376(5) 0.6147(3) 0.3709(3) 0.0249(12) Uani 1 1 d . . . . .
C15 C 1.0884(6) 0.5775(3) 0.3263(4) 0.0296(13) Uani 1 1 d . . . . .
H15 H 1.135888 0.548092 0.344396 0.036 Uiso 1 1 calc R . . . .
C16 C 1.0741(7) 0.5806(3) 0.2570(4) 0.0344(15) Uani 1 1 d . . . . .
H16 H 1.114971 0.555274 0.228745 0.041 Uiso 1 1 calc R . . . .
C17 C 0.9994(6) 0.6210(3) 0.2296(3) 0.0303(13) Uani 1 1 d . . . . .
H17 H 0.985010 0.622166 0.182311 0.036 Uiso 1 1 calc R . . . .
C18 C 0.9448(6) 0.6604(3) 0.2711(3) 0.0267(13) Uani 1 1 d . . . . .
C19 C 0.8650(6) 0.7004(3) 0.2390(3) 0.0256(12) Uani 1 1 d . . . . .
H19 H 0.846291 0.694873 0.192635 0.031 Uiso 1 1 calc R . . . .
C20 C 0.7344(7) 0.7762(3) 0.2252(4) 0.0340(15) Uani 1 1 d . . . . .
H20A H 0.650174 0.772284 0.241207 0.051 Uiso 1 1 calc GR . . . .
H20B H 0.738098 0.764002 0.178273 0.051 Uiso 1 1 calc GR . . . .
H20C H 0.759356 0.814819 0.228263 0.051 Uiso 1 1 calc GR . . . .
C21 C 1.0549(6) 0.6099(3) 0.4470(3) 0.0258(12) Uani 1 1 d . . . . .
C22 C 0.9310(7) 0.6043(3) 0.4807(4) 0.0354(15) Uani 1 1 d . . . . .
H22A H 0.880031 0.636373 0.469713 0.053 Uiso 1 1 calc GR . . . .
H22B H 0.943425 0.602056 0.529625 0.053 Uiso 1 1 calc GR . . . .
H22C H 0.889887 0.570910 0.464498 0.053 Uiso 1 1 calc GR . . . .
C23 C 1.1326(7) 0.5589(3) 0.4664(4) 0.0339(15) Uani 1 1 d . . . . .
H23A H 1.090149 0.525575 0.450916 0.051 Uiso 1 1 calc GR . . . .
H23B H 1.143931 0.557494 0.515415 0.051 Uiso 1 1 calc GR . . . .
H23C H 1.212969 0.561271 0.445088 0.051 Uiso 1 1 calc GR . . . .
C24 C 1.1266(7) 0.6603(3) 0.4734(4) 0.0326(14) Uani 1 1 d . . . . .
H24A H 1.209648 0.659964 0.455075 0.049 Uiso 1 1 calc GR . . . .
H24B H 1.131770 0.658956 0.522660 0.049 Uiso 1 1 calc GR . . . .
H24C H 1.084127 0.693935 0.459170 0.049 Uiso 1 1 calc GR . . . .
Fe2 Fe 0.36661(9) 0.74017(4) 0.16090(5) 0.0236(2) Uani 1 1 d . . . . .
Cl2 Cl 0.17522(15) 0.71534(7) 0.13105(8) 0.0336(3) Uani 1 1 d . . . . .
O3 O 0.4637(4) 0.68498(19) 0.1999(2) 0.0279(9) Uani 1 1 d . . . . .
O4 O 0.4202(4) 0.81165(18) 0.1432(2) 0.0265(9) Uani 1 1 d . . . . .
N3 N 0.4399(5) 0.7176(2) 0.0674(3) 0.0292(11) Uani 1 1 d . . . . .
N4 N 0.3263(5) 0.7674(2) 0.2588(3) 0.0277(11) Uani 1 1 d . . . . .
C25 C 0.5505(6) 0.6513(2) 0.1795(3) 0.0264(12) Uani 1 1 d . . . . .
C26 C 0.6033(6) 0.6116(3) 0.2256(3) 0.0277(13) Uani 1 1 d . . . . .
C27 C 0.6957(6) 0.5781(3) 0.2022(4) 0.0354(15) Uani 1 1 d . . . . .
H27 H 0.731565 0.552153 0.232398 0.042 Uiso 1 1 calc R . . . .
C28 C 0.7392(7) 0.5804(3) 0.1365(4) 0.0382(16) Uani 1 1 d . . . . .
H28 H 0.803485 0.556832 0.122589 0.046 Uiso 1 1 calc R . . . .
C29 C 0.6873(6) 0.6174(3) 0.0924(4) 0.0340(15) Uani 1 1 d . . . . .
H29 H 0.716396 0.619355 0.047652 0.041 Uiso 1 1 calc R . . . .
C30 C 0.5915(6) 0.6526(3) 0.1122(4) 0.0305(14) Uani 1 1 d . . . . .
C31 C 0.5336(6) 0.6855(3) 0.0602(3) 0.0293(13) Uani 1 1 d . . . . .
H31 H 0.567435 0.683487 0.016564 0.035 Uiso 1 1 calc R . . . .
C32 C 0.3883(7) 0.7428(3) 0.0062(3) 0.0353(15) Uani 1 1 d . . . . .
H32A H 0.306380 0.727653 -0.003150 0.053 Uiso 1 1 calc GR . . . .
H32B H 0.441888 0.734983 -0.031807 0.053 Uiso 1 1 calc GR . . . .
H32C H 0.382281 0.782633 0.012520 0.053 Uiso 1 1 calc GR . . . .
C33 C 0.5543(7) 0.6054(3) 0.2968(4) 0.0321(14) Uani 1 1 d . . . . .
C34 C 0.5692(7) 0.6591(3) 0.3366(4) 0.0366(15) Uani 1 1 d . . . . .
H34A H 0.655867 0.670060 0.337452 0.055 Uiso 1 1 calc GR . . . .
H34B H 0.541448 0.653606 0.382769 0.055 Uiso 1 1 calc GR . . . .
H34C H 0.519826 0.688038 0.314949 0.055 Uiso 1 1 calc GR . . . .
C35 C 0.6229(8) 0.5604(3) 0.3367(4) 0.0447(18) Uani 1 1 d . . . . .
H35A H 0.616137 0.525425 0.312392 0.067 Uiso 1 1 calc GR . . . .
H35B H 0.586664 0.556503 0.381254 0.067 Uiso 1 1 calc GR . . . .
H35C H 0.709754 0.570468 0.341820 0.067 Uiso 1 1 calc GR . . . .
C36 C 0.4186(7) 0.5883(3) 0.2932(4) 0.0356(15) Uani 1 1 d . . . . .
H36A H 0.369610 0.618158 0.273374 0.053 Uiso 1 1 calc GR . . . .
H36B H 0.389726 0.580448 0.338646 0.053 Uiso 1 1 calc GR . . . .
H36C H 0.409846 0.555300 0.265213 0.053 Uiso 1 1 calc GR . . . .
C37 C 0.4709(6) 0.8515(2) 0.1827(3) 0.0253(12) Uani 1 1 d . . . . .
C38 C 0.5417(6) 0.8937(3) 0.1532(3) 0.0260(12) Uani 1 1 d . . . . .
C39 C 0.5951(6) 0.9322(3) 0.1972(3) 0.0292(13) Uani 1 1 d . . . . .
H39 H 0.643884 0.960610 0.178747 0.035 Uiso 1 1 calc R . . . .
C40 C 0.5802(6) 0.9310(3) 0.2664(4) 0.0335(14) Uani 1 1 d . . . . .
H40 H 0.619307 0.957537 0.294565 0.040 Uiso 1 1 calc R . . . .
C41 C 0.5077(6) 0.8906(3) 0.2934(3) 0.0308(14) Uani 1 1 d . . . . .
H41 H 0.494859 0.890105 0.340628 0.037 Uiso 1 1 calc R . . . .
C42 C 0.4524(6) 0.8502(3) 0.2530(3) 0.0267(12) Uani 1 1 d . . . . .
C43 C 0.3749(6) 0.8105(3) 0.2859(3) 0.0281(13) Uani 1 1 d . . . . .
H43 H 0.358352 0.816760 0.332065 0.034 Uiso 1 1 calc R . . . .
C44 C 0.2441(7) 0.7344(3) 0.3002(4) 0.0372(16) Uani 1 1 d . . . . .
H44A H 0.162183 0.733453 0.278989 0.056 Uiso 1 1 calc GR . . . .
H44B H 0.238844 0.750859 0.345089 0.056 Uiso 1 1 calc GR . . . .
H44C H 0.276367 0.696965 0.304123 0.056 Uiso 1 1 calc GR . . . .
C45 C 0.5611(6) 0.8967(3) 0.0770(3) 0.0275(13) Uani 1 1 d . . . . .
C46 C 0.6280(6) 0.8450(3) 0.0529(3) 0.0306(13) Uani 1 1 d . . . . .
H46A H 0.706195 0.841201 0.077716 0.046 Uiso 1 1 calc GR . . . .
H46B H 0.643768 0.848108 0.004659 0.046 Uiso 1 1 calc GR . . . .
H46C H 0.576812 0.812609 0.061056 0.046 Uiso 1 1 calc GR . . . .
C47 C 0.4354(6) 0.9029(3) 0.0408(3) 0.0314(14) Uani 1 1 d . . . . .
H47A H 0.381779 0.872380 0.053377 0.047 Uiso 1 1 calc GR . . . .
H47B H 0.446813 0.902636 -0.008026 0.047 Uiso 1 1 calc GR . . . .
H47C H 0.397578 0.937751 0.054052 0.047 Uiso 1 1 calc GR . . . .
C48 C 0.6390(7) 0.9474(3) 0.0579(4) 0.0354(15) Uani 1 1 d . . . . .
H48A H 0.592108 0.980969 0.066401 0.053 Uiso 1 1 calc GR . . . .
H48B H 0.659180 0.945480 0.010036 0.053 Uiso 1 1 calc GR . . . .
H48C H 0.714976 0.947789 0.085065 0.053 Uiso 1 1 calc GR . . . .
C49 C 0.0267(8) 0.5021(4) 0.0897(5) 0.052(2) Uani 1 1 d . . . . .
H49A H 0.002663 0.503385 0.136990 0.078 Uiso 1 1 calc GR . . . .
H49B H -0.001835 0.467604 0.069392 0.078 Uiso 1 1 calc GR . . . .
H49C H -0.010471 0.533166 0.065390 0.078 Uiso 1 1 calc GR . . . .
C50 C 0.1619(7) 0.5055(3) 0.0856(4) 0.0367(16) Uani 1 1 d . . . . .
C51 C 0.2231(8) 0.5543(3) 0.0999(4) 0.0432(18) Uani 1 1 d . . . . .
H51 H 0.177370 0.585898 0.111925 0.052 Uiso 1 1 calc R . . . .
C52 C 0.3507(9) 0.5575(5) 0.0968(4) 0.057(3) Uani 1 1 d . . . . .
H52 H 0.391307 0.590788 0.108338 0.069 Uiso 1 1 calc R . . . .
C53 C 0.4178(9) 0.5131(6) 0.0772(5) 0.065(3) Uani 1 1 d . . . . .
H53 H 0.504613 0.515927 0.074212 0.078 Uiso 1 1 calc R . . . .
C54 C 0.3604(9) 0.4644(5) 0.0618(4) 0.058(2) Uani 1 1 d . . . . .
H54 H 0.407532 0.433690 0.047721 0.069 Uiso 1 1 calc R . . . .
C55 C 0.2306(8) 0.4596(4) 0.0668(4) 0.0455(19) Uani 1 1 d . . . . .
H55 H 0.191013 0.425624 0.057427 0.055 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 Cl1 2.2454(19) . ?
Fe1 O1 1.880(5) . ?
Fe1 O2 1.881(4) . ?
Fe1 N1 2.103(6) . ?
Fe1 N2 2.108(6) . ?
O1 C1 1.318(8) . ?
O2 C13 1.342(7) . ?
N1 C7 1.297(9) . ?
N1 C8 1.471(9) . ?
N2 C19 1.283(9) . ?
N2 C20 1.458(8) . ?
C1 C2 1.443(9) . ?
C1 C6 1.434(9) . ?
C2 C3 1.401(10) . ?
C2 C9 1.527(10) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(11) . ?
C4 H4 0.9500 . ?
C4 C5 1.368(11) . ?
C5 H5 0.9500 . ?
C5 C6 1.409(10) . ?
C6 C7 1.430(10) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.544(10) . ?
C9 C11 1.547(10) . ?
C9 C12 1.528(9) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.439(9) . ?
C13 C18 1.416(9) . ?
C14 C15 1.389(9) . ?
C14 C21 1.525(9) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(10) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(10) . ?
C17 H17 0.9500 . ?
C17 C18 1.403(9) . ?
C18 C19 1.446(9) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.522(9) . ?
C21 C23 1.548(9) . ?
C21 C24 1.540(9) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
Fe2 Cl2 2.2392(19) . ?
Fe2 O3 1.869(5) . ?
Fe2 O4 1.870(4) . ?
Fe2 N3 2.106(6) . ?
Fe2 N4 2.109(6) . ?
O3 C25 1.319(8) . ?
O4 C37 1.358(8) . ?
N3 C31 1.293(9) . ?
N3 C32 1.466(8) . ?
N4 C43 1.288(9) . ?
N4 C44 1.464(8) . ?
C25 C26 1.443(9) . ?
C25 C30 1.418(9) . ?
C26 C27 1.382(9) . ?
C26 C33 1.528(10) . ?
C27 H27 0.9500 . ?
C27 C28 1.398(11) . ?
C28 H28 0.9500 . ?
C28 C29 1.370(11) . ?
C29 H29 0.9500 . ?
C29 C30 1.411(10) . ?
C30 C31 1.442(10) . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.534(10) . ?
C33 C35 1.539(10) . ?
C33 C36 1.535(10) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.417(8) . ?
C37 C42 1.414(9) . ?
C38 C39 1.401(9) . ?
C38 C45 1.534(9) . ?
C39 H39 0.9500 . ?
C39 C40 1.386(10) . ?
C40 H40 0.9500 . ?
C40 C41 1.376(10) . ?
C41 H41 0.9500 . ?
C41 C42 1.399(10) . ?
C42 C43 1.447(9) . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 C46 1.534(9) . ?
C45 C47 1.542(9) . ?
C45 C48 1.549(9) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C49 C50 1.478(11) . ?
C50 C51 1.388(11) . ?
C50 C55 1.398(11) . ?
C51 H51 0.9500 . ?
C51 C52 1.394(13) . ?
C52 H52 0.9500 . ?
C52 C53 1.364(17) . ?
C53 H53 0.9500 . ?
C53 C54 1.373(16) . ?
C54 H54 0.9500 . ?
C54 C55 1.423(13) . ?
C55 H55 0.9500 . ?

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 Cl1 116.06(16) . . ?
O1 Fe1 O2 124.6(2) . . ?
O1 Fe1 N1 87.5(2) . . ?
O1 Fe1 N2 88.5(2) . . ?
O2 Fe1 Cl1 119.35(15) . . ?
O2 Fe1 N1 87.5(2) . . ?
O2 Fe1 N2 86.9(2) . . ?
N1 Fe1 Cl1 93.55(16) . . ?
N1 Fe1 N2 169.7(2) . . ?
N2 Fe1 Cl1 96.76(16) . . ?
C1 O1 Fe1 135.7(4) . . ?
C13 O2 Fe1 132.6(4) . . ?
C7 N1 Fe1 124.6(5) . . ?
C7 N1 C8 116.8(6) . . ?
C8 N1 Fe1 118.5(5) . . ?
C19 N2 Fe1 123.6(5) . . ?
C19 N2 C20 117.2(6) . . ?
C20 N2 Fe1 119.0(4) . . ?
O1 C1 C2 119.6(6) . . ?
O1 C1 C6 120.8(6) . . ?
C6 C1 C2 119.6(6) . . ?
C1 C2 C9 121.1(6) . . ?
C3 C2 C1 116.8(6) . . ?
C3 C2 C9 122.1(6) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 C2 123.0(7) . . ?
C4 C3 H3 118.5 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(7) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(7) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 119.9(6) . . ?
C5 C6 C7 117.0(6) . . ?
C7 C6 C1 122.8(6) . . ?
N1 C7 C6 126.8(6) . . ?
N1 C7 H7 116.6 . . ?
C6 C7 H7 116.6 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C9 C10 108.9(6) . . ?
C2 C9 C11 110.3(5) . . ?
C2 C9 C12 112.3(6) . . ?
C10 C9 C11 109.5(6) . . ?
C12 C9 C10 108.2(6) . . ?
C12 C9 C11 107.5(6) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 C14 119.7(5) . . ?
O2 C13 C18 120.4(6) . . ?
C18 C13 C14 119.9(5) . . ?
C13 C14 C21 120.9(5) . . ?
C15 C14 C13 116.5(6) . . ?
C15 C14 C21 122.6(6) . . ?
C14 C15 H15 118.0 . . ?
C16 C15 C14 124.0(6) . . ?
C16 C15 H15 118.0 . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.1(6) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(6) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C19 122.8(6) . . ?
C17 C18 C13 119.8(6) . . ?
C17 C18 C19 117.3(6) . . ?
N2 C19 C18 126.7(6) . . ?
N2 C19 H19 116.6 . . ?
C18 C19 H19 116.6 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C21 C23 111.4(5) . . ?
C14 C21 C24 109.2(5) . . ?
C22 C21 C14 110.3(5) . . ?
C22 C21 C23 107.7(5) . . ?
C22 C21 C24 111.7(6) . . ?
C24 C21 C23 106.4(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 Fe2 Cl2 115.64(16) . . ?
O3 Fe2 O4 124.8(2) . . ?
O3 Fe2 N3 87.5(2) . . ?
O3 Fe2 N4 88.2(2) . . ?
O4 Fe2 Cl2 119.57(16) . . ?
O4 Fe2 N3 87.3(2) . . ?
O4 Fe2 N4 87.2(2) . . ?
N3 Fe2 Cl2 93.51(17) . . ?
N3 Fe2 N4 169.5(2) . . ?
N4 Fe2 Cl2 96.98(16) . . ?
C25 O3 Fe2 136.2(4) . . ?
C37 O4 Fe2 132.9(4) . . ?
C31 N3 Fe2 124.5(5) . . ?
C31 N3 C32 116.9(6) . . ?
C32 N3 Fe2 118.5(5) . . ?
C43 N4 Fe2 123.4(4) . . ?
C43 N4 C44 117.6(6) . . ?
C44 N4 Fe2 119.0(4) . . ?
O3 C25 C26 120.0(6) . . ?
O3 C25 C30 120.9(6) . . ?
C30 C25 C26 119.0(6) . . ?
C25 C26 C33 120.8(6) . . ?
C27 C26 C25 117.8(6) . . ?
C27 C26 C33 121.4(6) . . ?
C26 C27 H27 118.3 . . ?
C26 C27 C28 123.4(7) . . ?
C28 C27 H27 118.3 . . ?
C27 C28 H28 120.6 . . ?
C29 C28 C27 118.7(7) . . ?
C29 C28 H28 120.6 . . ?
C28 C29 H29 119.3 . . ?
C28 C29 C30 121.3(7) . . ?
C30 C29 H29 119.3 . . ?
C25 C30 C31 123.1(6) . . ?
C29 C30 C25 119.7(7) . . ?
C29 C30 C31 117.0(6) . . ?
N3 C31 C30 126.3(6) . . ?
N3 C31 H31 116.9 . . ?
C30 C31 H31 116.9 . . ?
N3 C32 H32A 109.5 . . ?
N3 C32 H32B 109.5 . . ?
N3 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C26 C33 C34 110.9(6) . . ?
C26 C33 C35 111.9(6) . . ?
C26 C33 C36 109.5(6) . . ?
C34 C33 C35 107.2(6) . . ?
C34 C33 C36 110.4(6) . . ?
C36 C33 C35 106.8(6) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O4 C37 C38 119.8(6) . . ?
O4 C37 C42 119.4(5) . . ?
C42 C37 C38 120.8(6) . . ?
C37 C38 C45 121.9(6) . . ?
C39 C38 C37 116.7(6) . . ?
C39 C38 C45 121.4(6) . . ?
C38 C39 H39 118.3 . . ?
C40 C39 C38 123.4(6) . . ?
C40 C39 H39 118.3 . . ?
C39 C40 H40 120.7 . . ?
C41 C40 C39 118.6(7) . . ?
C41 C40 H40 120.7 . . ?
C40 C41 H41 119.3 . . ?
C40 C41 C42 121.5(6) . . ?
C42 C41 H41 119.3 . . ?
C37 C42 C43 123.7(6) . . ?
C41 C42 C37 119.0(6) . . ?
C41 C42 C43 117.3(6) . . ?
N4 C43 C42 126.5(6) . . ?
N4 C43 H43 116.8 . . ?
C42 C43 H43 116.8 . . ?
N4 C44 H44A 109.5 . . ?
N4 C44 H44B 109.5 . . ?
N4 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C38 C45 C46 110.0(5) . . ?
C38 C45 C47 109.2(5) . . ?
C38 C45 C48 111.4(6) . . ?
C46 C45 C47 111.0(6) . . ?
C46 C45 C48 108.2(5) . . ?
C47 C45 C48 107.0(5) . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C50 C49 H49A 109.5 . . ?
C50 C49 H49B 109.5 . . ?
C50 C49 H49C 109.5 . . ?
C51 C50 C49 120.7(8) . . ?
C51 C50 C55 118.7(8) . . ?
C55 C50 C49 120.6(8) . . ?
C50 C51 H51 119.5 . . ?
C50 C51 C52 120.9(9) . . ?
C52 C51 H51 119.5 . . ?
C51 C52 H52 119.8 . . ?
C53 C52 C51 120.5(9) . . ?
C53 C52 H52 119.8 . . ?
C52 C53 H53 119.9 . . ?
C52 C53 C54 120.3(9) . . ?
C54 C53 H53 119.9 . . ?
C53 C54 H54 119.9 . . ?
C53 C54 C55 120.2(10) . . ?
C55 C54 H54 119.9 . . ?
C50 C55 C54 119.4(9) . . ?
C50 C55 H55 120.3 . . ?
C54 C55 H55 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O1 C1 C2 175.8(4) . . . . ?
Fe1 O1 C1 C6 -4.4(10) . . . . ?
Fe1 O2 C13 C14 159.1(4) . . . . ?
Fe1 O2 C13 C18 -21.7(9) . . . . ?
Fe1 N1 C7 C6 6.5(9) . . . . ?
Fe1 N2 C19 C18 7.7(9) . . . . ?
Cl1 Fe1 O1 C1 104.7(6) . . . . ?
Cl1 Fe1 O2 C13 125.4(5) . . . . ?
O1 Fe1 O2 C13 -56.6(6) . . . . ?
O1 C1 C2 C3 -177.6(6) . . . . ?
O1 C1 C2 C9 3.1(9) . . . . ?
O1 C1 C6 C5 178.3(6) . . . . ?
O1 C1 C6 C7 -7.9(10) . . . . ?
O2 Fe1 O1 C1 -73.3(6) . . . . ?
O2 C13 C14 C15 -177.6(6) . . . . ?
O2 C13 C14 C21 2.9(9) . . . . ?
O2 C13 C18 C17 177.5(6) . . . . ?
O2 C13 C18 C19 -4.7(9) . . . . ?
N1 Fe1 O1 C1 12.0(6) . . . . ?
N1 Fe1 O2 C13 -141.9(6) . . . . ?
N2 Fe1 O1 C1 -158.5(6) . . . . ?
N2 Fe1 O2 C13 29.4(5) . . . . ?
C1 C2 C3 C4 -1.5(10) . . . . ?
C1 C2 C9 C10 59.6(8) . . . . ?
C1 C2 C9 C11 -60.6(8) . . . . ?
C1 C2 C9 C12 179.5(6) . . . . ?
C1 C6 C7 N1 6.0(11) . . . . ?
C2 C1 C6 C5 -1.9(9) . . . . ?
C2 C1 C6 C7 171.8(6) . . . . ?
C2 C3 C4 C5 -0.4(11) . . . . ?
C3 C2 C9 C10 -119.7(7) . . . . ?
C3 C2 C9 C11 120.1(7) . . . . ?
C3 C2 C9 C12 0.2(9) . . . . ?
C3 C4 C5 C6 1.3(11) . . . . ?
C4 C5 C6 C1 0.0(10) . . . . ?
C4 C5 C6 C7 -174.2(6) . . . . ?
C5 C6 C7 N1 179.9(6) . . . . ?
C6 C1 C2 C3 2.7(9) . . . . ?
C6 C1 C2 C9 -176.7(6) . . . . ?
C8 N1 C7 C6 -178.7(6) . . . . ?
C9 C2 C3 C4 177.8(6) . . . . ?
C13 C14 C15 C16 0.3(10) . . . . ?
C13 C14 C21 C22 59.0(8) . . . . ?
C13 C14 C21 C23 178.6(6) . . . . ?
C13 C14 C21 C24 -64.2(7) . . . . ?
C13 C18 C19 N2 9.8(10) . . . . ?
C14 C13 C18 C17 -3.2(9) . . . . ?
C14 C13 C18 C19 174.6(6) . . . . ?
C14 C15 C16 C17 -3.8(11) . . . . ?
C15 C14 C21 C22 -120.5(7) . . . . ?
C15 C14 C21 C23 -0.9(9) . . . . ?
C15 C14 C21 C24 116.4(7) . . . . ?
C15 C16 C17 C18 3.8(11) . . . . ?
C16 C17 C18 C13 -0.3(10) . . . . ?
C16 C17 C18 C19 -178.2(6) . . . . ?
C17 C18 C19 N2 -172.3(6) . . . . ?
C18 C13 C14 C15 3.2(9) . . . . ?
C18 C13 C14 C21 -176.3(5) . . . . ?
C20 N2 C19 C18 -177.2(6) . . . . ?
C21 C14 C15 C16 179.8(6) . . . . ?
Fe2 O3 C25 C26 -178.0(5) . . . . ?
Fe2 O3 C25 C30 0.6(10) . . . . ?
Fe2 O4 C37 C38 157.5(5) . . . . ?
Fe2 O4 C37 C42 -22.4(9) . . . . ?
Fe2 N3 C31 C30 11.0(10) . . . . ?
Fe2 N4 C43 C42 7.3(9) . . . . ?
Cl2 Fe2 O3 C25 99.9(6) . . . . ?
Cl2 Fe2 O4 C37 126.2(5) . . . . ?
O3 Fe2 O4 C37 -56.1(6) . . . . ?
O3 C25 C26 C27 -178.7(6) . . . . ?
O3 C25 C26 C33 3.9(9) . . . . ?
O3 C25 C30 C29 177.9(6) . . . . ?
O3 C25 C30 C31 -7.1(10) . . . . ?
O4 Fe2 O3 C25 -77.9(7) . . . . ?
O4 C37 C38 C39 -177.7(6) . . . . ?
O4 C37 C38 C45 1.4(9) . . . . ?
O4 C37 C42 C41 178.3(6) . . . . ?
O4 C37 C42 C43 -4.1(9) . . . . ?
N3 Fe2 O3 C25 7.2(6) . . . . ?
N3 Fe2 O4 C37 -141.3(6) . . . . ?
N4 Fe2 O3 C25 -163.2(6) . . . . ?
N4 Fe2 O4 C37 29.8(6) . . . . ?
C25 C26 C27 C28 -0.7(11) . . . . ?
C25 C26 C33 C34 -61.0(8) . . . . ?
C25 C26 C33 C35 179.3(6) . . . . ?
C25 C26 C33 C36 61.2(8) . . . . ?
C25 C30 C31 N3 0.4(11) . . . . ?
C26 C25 C30 C29 -3.4(9) . . . . ?
C26 C25 C30 C31 171.5(6) . . . . ?
C26 C27 C28 C29 -0.6(12) . . . . ?
C27 C26 C33 C34 121.7(7) . . . . ?
C27 C26 C33 C35 2.0(9) . . . . ?
C27 C26 C33 C36 -116.2(7) . . . . ?
C27 C28 C29 C30 -0.2(11) . . . . ?
C28 C29 C30 C25 2.2(11) . . . . ?
C28 C29 C30 C31 -173.1(7) . . . . ?
C29 C30 C31 N3 175.5(7) . . . . ?
C30 C25 C26 C27 2.7(9) . . . . ?
C30 C25 C26 C33 -174.7(6) . . . . ?
C32 N3 C31 C30 -173.9(6) . . . . ?
C33 C26 C27 C28 176.7(7) . . . . ?
C37 C38 C39 C40 -0.8(10) . . . . ?
C37 C38 C45 C46 -61.5(8) . . . . ?
C37 C38 C45 C47 60.6(8) . . . . ?
C37 C38 C45 C48 178.6(6) . . . . ?
C37 C42 C43 N4 9.8(10) . . . . ?
C38 C37 C42 C41 -1.6(9) . . . . ?
C38 C37 C42 C43 176.0(6) . . . . ?
C38 C39 C40 C41 -1.2(10) . . . . ?
C39 C38 C45 C46 117.6(7) . . . . ?
C39 C38 C45 C47 -120.4(7) . . . . ?
C39 C38 C45 C48 -2.4(9) . . . . ?
C39 C40 C41 C42 1.9(10) . . . . ?
C40 C41 C42 C37 -0.5(10) . . . . ?
C40 C41 C42 C43 -178.3(6) . . . . ?
C41 C42 C43 N4 -172.6(6) . . . . ?
C42 C37 C38 C39 2.2(9) . . . . ?
C42 C37 C38 C45 -178.7(6) . . . . ?
C44 N4 C43 C42 -176.1(6) . . . . ?
C45 C38 C39 C40 -179.9(6) . . . . ?
C49 C50 C51 C52 179.4(8) . . . . ?
C49 C50 C55 C54 178.6(8) . . . . ?
C50 C51 C52 C53 2.4(13) . . . . ?
C51 C50 C55 C54 -0.9(12) . . . . ?
C51 C52 C53 C54 -1.5(14) . . . . ?
C52 C53 C54 C55 -0.7(14) . . . . ?
C53 C54 C55 C50 1.9(13) . . . . ?
C55 C50 C51 C52 -1.2(12) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.495
_oxdiff_exptl_absorpt_empirical_full_min 0.702
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.863(4)
2 0.137(4)

