# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_tlcr12
_database_code_depnum_ccdc_archive 'CCDC 1855298'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2019-07-13 deposited with the CCDC.	2019-10-23 downloaded from the CCDC.
;
_audit_creation_date             2019-07-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H28 Cl Fe N2 O6'
_chemical_formula_sum            'C28 H28 Cl Fe N2 O6'
_chemical_formula_weight         579.82
_chemical_melting_point          ?
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                   16.0599(7)
_cell_length_b                   10.4661(3)
_cell_length_c                   16.9384(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.324(3)
_cell_angle_gamma                90
_cell_volume                     2686.68(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13316
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.92
_cell_measurement_theta_min      5.14
_shelx_estimated_absorpt_T_max   0.722
_shelx_estimated_absorpt_T_min   0.362
_exptl_absorpt_coefficient_mu    5.798
_exptl_absorpt_correction_T_max  0.142
_exptl_absorpt_correction_T_min  0.035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark brown'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1204
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13540
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.605
_diffrn_reflns_theta_min         5.136
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari with Xenocs Genix3D Cu HF'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2337
_reflns_number_total             2584
_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       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2584
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²+4.1217P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0744
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.500000 0.70303(4) 0.750000 0.01381(11) Uani 1 2 d S T P . .
Cl1 Cl 0.500000 0.91648(6) 0.750000 0.02749(17) Uani 1 2 d S T P . .
O1 O 0.42692(8) 0.62721(13) 0.65066(8) 0.0184(3) Uani 1 1 d . . . . .
O2 O 0.77264(9) 0.84063(13) 0.69615(8) 0.0219(3) Uani 1 1 d . . . . .
O3 O 0.27989(8) 0.58544(13) 0.53069(8) 0.0192(3) Uani 1 1 d . . . . .
N1 N 0.60354(10) 0.68623(15) 0.69991(9) 0.0162(3) Uani 1 1 d . . . . .
C1 C 0.42999(12) 0.63588(17) 0.57358(11) 0.0162(4) Uani 1 1 d . . . . .
C2 C 0.35136(12) 0.61171(17) 0.50633(11) 0.0169(4) Uani 1 1 d . . . . .
C3 C 0.35159(12) 0.61510(18) 0.42483(11) 0.0197(4) Uani 1 1 d . . . . .
H3 H 0.298863 0.597253 0.380034 0.024 Uiso 1 1 calc R . . . .
C4 C 0.42910(13) 0.64470(19) 0.40781(11) 0.0210(4) Uani 1 1 d . . . . .
H4 H 0.428443 0.648670 0.351578 0.025 Uiso 1 1 calc R . . . .
C5 C 0.50570(13) 0.66787(18) 0.47219(11) 0.0194(4) Uani 1 1 d . . . . .
H5 H 0.558163 0.686816 0.460264 0.023 Uiso 1 1 calc R . . . .
C6 C 0.50766(12) 0.66394(17) 0.55596(11) 0.0170(4) Uani 1 1 d . . . . .
C7 C 0.59183(12) 0.68111(17) 0.62148(11) 0.0166(4) Uani 1 1 d . . . . .
H7 H 0.642561 0.689247 0.604847 0.020 Uiso 1 1 calc R . . . .
C8 C 0.69349(12) 0.7009(2) 0.76167(11) 0.0214(4) Uani 1 1 d . . . . .
H8A H 0.692698 0.774205 0.798343 0.026 Uiso 1 1 calc R . . . .
H8B H 0.706999 0.623520 0.797280 0.026 Uiso 1 1 calc R . . . .
C9 C 0.76651(12) 0.72092(18) 0.72760(11) 0.0177(4) Uani 1 1 d . . . . .
C10 C 0.83212(12) 0.64579(19) 0.72201(11) 0.0201(4) Uani 1 1 d . . . . .
H10 H 0.842591 0.559288 0.739483 0.024 Uiso 1 1 calc R . . . .
C11 C 0.88321(13) 0.7216(2) 0.68453(12) 0.0220(4) Uani 1 1 d . . . . .
H11 H 0.934122 0.695124 0.672183 0.026 Uiso 1 1 calc R . . . .
C12 C 0.84531(13) 0.8370(2) 0.67028(12) 0.0233(4) Uani 1 1 d . . . . .
H12 H 0.865722 0.906738 0.645750 0.028 Uiso 1 1 calc R . . . .
C13 C 0.19787(12) 0.5569(2) 0.46595(12) 0.0229(4) Uani 1 1 d . . . . .
H13A H 0.205213 0.482997 0.432413 0.027 Uiso 1 1 calc R . . . .
H13B H 0.178075 0.631282 0.428234 0.027 Uiso 1 1 calc R . . . .
C14 C 0.13103(13) 0.5264(2) 0.50841(13) 0.0271(4) Uani 1 1 d . . . . .
H14A H 0.074170 0.506225 0.466012 0.041 Uiso 1 1 calc GR . . . .
H14B H 0.124158 0.600446 0.541165 0.041 Uiso 1 1 calc GR . . . .
H14C H 0.151405 0.452868 0.545599 0.041 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 2.2339(8) . ?
Fe1 O1 1.8793(12) 2_656 ?
Fe1 O1 1.8792(12) . ?
Fe1 N1 2.1094(15) . ?
Fe1 N1 2.1093(15) 2_656 ?
O1 C1 1.326(2) . ?
O2 C9 1.378(2) . ?
O2 C12 1.376(2) . ?
O3 C2 1.370(2) . ?
O3 C13 1.439(2) . ?
N1 C7 1.280(2) . ?
N1 C8 1.485(2) . ?
C1 C2 1.416(2) . ?
C1 C6 1.406(3) . ?
C2 C3 1.382(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.402(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.369(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.410(3) . ?
C6 C7 1.449(3) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.483(3) . ?
C9 C10 1.343(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.432(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.338(3) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.511(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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 114.98(4) 2_656 . ?
O1 Fe1 Cl1 114.98(4) . . ?
O1 Fe1 O1 130.04(9) . 2_656 ?
O1 Fe1 N1 89.03(6) . 2_656 ?
O1 Fe1 N1 86.93(6) . . ?
O1 Fe1 N1 86.94(6) 2_656 2_656 ?
O1 Fe1 N1 89.03(6) 2_656 . ?
N1 Fe1 Cl1 94.78(4) 2_656 . ?
N1 Fe1 Cl1 94.78(4) . . ?
N1 Fe1 N1 170.43(9) 2_656 . ?
C1 O1 Fe1 129.57(12) . . ?
C12 O2 C9 105.96(15) . . ?
C2 O3 C13 117.33(14) . . ?
C7 N1 Fe1 123.81(13) . . ?
C7 N1 C8 120.67(15) . . ?
C8 N1 Fe1 114.88(11) . . ?
O1 C1 C2 117.79(16) . . ?
O1 C1 C6 123.23(16) . . ?
C6 C1 C2 118.96(16) . . ?
O3 C2 C1 114.00(15) . . ?
O3 C2 C3 125.83(17) . . ?
C3 C2 C1 120.17(17) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.46(17) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.03(17) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.77(18) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.60(17) . . ?
C1 C6 C7 122.12(16) . . ?
C5 C6 C7 118.16(17) . . ?
N1 C7 C6 125.44(17) . . ?
N1 C7 H7 117.3 . . ?
C6 C7 H7 117.3 . . ?
N1 C8 H8A 108.1 . . ?
N1 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
C9 C8 N1 116.79(15) . . ?
C9 C8 H8A 108.1 . . ?
C9 C8 H8B 108.1 . . ?
O2 C9 C8 116.47(16) . . ?
C10 C9 O2 110.31(16) . . ?
C10 C9 C8 133.19(18) . . ?
C9 C10 H10 126.7 . . ?
C9 C10 C11 106.54(17) . . ?
C11 C10 H10 126.7 . . ?
C10 C11 H11 126.7 . . ?
C12 C11 C10 106.69(17) . . ?
C12 C11 H11 126.7 . . ?
O2 C12 H12 124.7 . . ?
C11 C12 O2 110.50(17) . . ?
C11 C12 H12 124.7 . . ?
O3 C13 H13A 110.3 . . ?
O3 C13 H13B 110.3 . . ?
O3 C13 C14 107.25(15) . . ?
H13A C13 H13B 108.5 . . ?
C14 C13 H13A 110.3 . . ?
C14 C13 H13B 110.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
