# Electronic Supplementary Material (ESI) for ChemComm.
# 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_e2917n
_database_code_depnum_ccdc_archive 'CCDC 1413936'
_audit_update_record             
;
2018-08-10 deposited with the CCDC.
2018-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H18 Co N6 S2'
_chemical_formula_sum            'C30 H18 Co N6 S2'
_chemical_formula_weight         585.55

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'

_cell_length_a                   18.3008(5)
_cell_length_b                   18.3008(5)
_cell_length_c                   15.2850(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4433.4(3)
_cell_formula_units_Z            3
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    38000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.658
_exptl_crystal_F_000             897
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.375
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38620
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.959
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             8626
_reflns_number_gt                6305
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.993

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0243P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2327 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8626
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_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_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
Co1 Co 0.20113(2) 0.20113(2) 0.0000 0.02261(11) Uani 1 2 d S T P . .
N1 N 0.31978(15) 0.31978(15) 0.0000 0.0281(7) Uani 1 2 d S T P . .
C1 C 0.32361(16) 0.39129(15) 0.02735(18) 0.0346(6) Uani 1 1 d . . . . .
H1 H 0.2733 0.3892 0.0468 0.042 Uiso 1 1 calc R U . . .
C2 C 0.39780(17) 0.46756(17) 0.02818(19) 0.0418(7) Uani 1 1 d . . . . .
H2 H 0.3980 0.5168 0.0480 0.050 Uiso 1 1 calc R U . . .
C3 C 0.47264(18) 0.47264(18) 0.0000 0.0314(9) Uani 1 2 d S T P . .
C4 C 0.55391(18) 0.55391(18) 0.0000 0.0349(9) Uani 1 2 d S T P . .
C5 C 0.57107(15) 0.61165(15) 0.06646(17) 0.0370(7) Uani 1 1 d . . . . .
H5 H 0.5310 0.5993 0.1117 0.044 Uiso 1 1 calc R U . . .
C6 C 0.64688(16) 0.68761(15) 0.06710(16) 0.0370(6) Uani 1 1 d . . . . .
C7 C 0.67025(16) 0.75370(15) 0.13585(16) 0.0333(6) Uani 1 1 d . . . . .
C8 C 0.69987(18) 0.74670(17) 0.2163(2) 0.0500(8) Uani 1 1 d . . . . .
H8 H 0.6979 0.6958 0.2332 0.060 Uiso 1 1 calc R U . . .
C9 C 0.73300(18) 0.81642(17) 0.27251(18) 0.0415(7) Uani 1 1 d . . . . .
H9 H 0.7540 0.8115 0.3277 0.050 Uiso 1 1 calc R U . . .
N2 N 0.73675(12) 0.88819(12) 0.25346(12) 0.0282(4) Uani 1 1 d . . . . .
C10 C 0.70279(16) 0.89218(17) 0.17726(18) 0.0384(6) Uani 1 1 d . . . . .
H10 H 0.7016 0.9422 0.1637 0.046 Uiso 1 1 calc R U . . .
C11 C 0.66949(17) 0.82706(18) 0.11769(18) 0.0447(7) Uani 1 1 d . . . . .
H11 H 0.6461 0.8327 0.0643 0.054 Uiso 1 1 calc R U . . .
C12 C 0.7063(2) 0.7063(2) 0.0000 0.0352(9) Uani 1 2 d S T P . .
C13 C -0.2160(2) -0.2160(2) 0.0000 0.0429(10) Uani 1 2 d S T P . .
C14 C -0.1505(2) -0.1505(2) 0.0000 0.0416(10) Uani 1 2 d S T P . .
C15 C -0.07276(18) -0.07276(18) 0.0000 0.0388(10) Uani 1 2 d S T P . .
C16 C -0.00477(18) -0.06202(18) -0.0493(2) 0.0556(9) Uani 1 1 d . . . . .
H16 H -0.0091 -0.1071 -0.0840 0.067 Uiso 1 1 calc R U . . .
C17 C 0.06953(16) 0.01464(16) -0.04798(19) 0.0431(7) Uani 1 1 d . . . . .
H17 H 0.1152 0.0208 -0.0830 0.052 Uiso 1 1 calc R U . . .
N3 N 0.08081(14) 0.08081(14) 0.0000 0.0296(7) Uani 1 2 d S T P . .
N4 N 0.16197(14) 0.23912(14) 0.11174(13) 0.0356(4) Uani 1 1 d . . . . .
C18 C 0.14555(17) 0.26434(17) 0.17173(16) 0.0356(4) Uani 1 1 d . . . . .
S1 S 0.12153(10) 0.29801(8) 0.26046(8) 0.1336(6) Uani 1 1 d . . . . .


_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
Co1 N4 2.101(2) . ?
Co1 N4 2.101(2) 4 ?
Co1 N2 2.1549(18) 6_655 ?
Co1 N2 2.1549(18) 3_564 ?
Co1 N1 2.171(3) . ?
Co1 N3 2.202(3) . ?
N1 C1 1.342(3) 4 ?
N1 C1 1.342(3) . ?
C1 C2 1.377(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.394(3) . ?
C2 H2 0.9500 . ?
C3 C2 1.394(3) 4 ?
C3 C4 1.487(5) . ?
C4 C5 1.384(3) 4 ?
C4 C5 1.384(3) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C12 1.407(3) . ?
C6 C7 1.494(3) . ?
C7 C8 1.375(4) . ?
C7 C11 1.378(4) . ?
C8 C9 1.401(4) . ?
C8 H8 0.9500 . ?
C9 N2 1.313(3) . ?
C9 H9 0.9500 . ?
N2 C10 1.339(3) . ?
N2 Co1 2.1549(18) 2_665 ?
C10 C11 1.376(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C6 1.407(3) 4 ?
C12 C13 1.423(5) 1_665 ?
C13 C14 1.198(5) . ?
C13 C12 1.422(5) 1_445 ?
C14 C15 1.422(5) . ?
C15 C16 1.383(3) 4 ?
C15 C16 1.383(3) . ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
C17 N3 1.340(3) . ?
C17 H17 0.9500 . ?
N3 C17 1.340(3) 4 ?
N4 C18 1.133(3) . ?
C18 S1 1.638(3) . ?

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
N4 Co1 N4 179.41(13) . 4 ?
N4 Co1 N2 91.05(7) . 6_655 ?
N4 Co1 N2 88.98(7) 4 6_655 ?
N4 Co1 N2 88.98(7) . 3_564 ?
N4 Co1 N2 91.05(7) 4 3_564 ?
N2 Co1 N2 173.95(11) 6_655 3_564 ?
N4 Co1 N1 90.29(6) . . ?
N4 Co1 N1 90.29(6) 4 . ?
N2 Co1 N1 86.97(5) 6_655 . ?
N2 Co1 N1 86.97(5) 3_564 . ?
N4 Co1 N3 89.71(6) . . ?
N4 Co1 N3 89.71(6) 4 . ?
N2 Co1 N3 93.03(5) 6_655 . ?
N2 Co1 N3 93.03(5) 3_564 . ?
N1 Co1 N3 180.00(16) . . ?
C1 N1 C1 118.2(3) 4 . ?
C1 N1 Co1 120.92(15) 4 . ?
C1 N1 Co1 120.92(15) . . ?
N1 C1 C2 122.4(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C2 116.7(3) . 4 ?
C2 C3 C4 121.65(16) . . ?
C2 C3 C4 121.64(16) 4 . ?
C5 C4 C5 120.6(3) 4 . ?
C5 C4 C3 119.69(16) 4 . ?
C5 C4 C3 119.69(16) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C12 120.1(2) . . ?
C5 C6 C7 123.6(2) . . ?
C12 C6 C7 116.2(2) . . ?
C8 C7 C11 117.9(2) . . ?
C8 C7 C6 121.3(2) . . ?
C11 C7 C6 120.6(2) . . ?
C7 C8 C9 118.4(3) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
N2 C9 C8 123.9(3) . . ?
N2 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
C9 N2 C10 117.0(2) . . ?
C9 N2 Co1 124.26(17) . 2_665 ?
C10 N2 Co1 118.68(16) . 2_665 ?
N2 C10 C11 123.0(3) . . ?
N2 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
C10 C11 C7 119.6(3) . . ?
C10 C11 H11 120.2 . . ?
C7 C11 H11 120.2 . . ?
C6 C12 C6 118.9(3) . 4 ?
C6 C12 C13 120.54(16) . 1_665 ?
C6 C12 C13 120.54(16) 4 1_665 ?
C14 C13 C12 180.0(7) . 1_445 ?
C13 C14 C15 180.0(6) . . ?
C16 C15 C16 117.2(3) 4 . ?
C16 C15 C14 121.41(17) 4 . ?
C16 C15 C14 121.41(17) . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
N3 C17 C16 123.7(3) . . ?
N3 C17 H17 118.2 . . ?
C16 C17 H17 118.2 . . ?
C17 N3 C17 116.2(3) 4 . ?
C17 N3 Co1 121.92(14) 4 . ?
C17 N3 Co1 121.91(14) . . ?
C18 N4 Co1 175.6(2) . . ?
N4 C18 S1 178.0(2) . . ?

_refine_diff_density_max         0.553
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.040

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_e3121a
_database_code_depnum_ccdc_archive 'CCDC 1413937'
_audit_update_record             
;
2018-08-10 deposited with the CCDC.
2018-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H18 Fe N6 S2 [+ solvent]'
_chemical_formula_sum            'C30 H18 Fe N6 S2'
_chemical_formula_weight         582.47

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'
'y, x, -z'

_cell_length_a                   18.3693(8)
_cell_length_b                   18.3693(8)
_cell_length_c                   15.2441(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4454.7(4)
_cell_formula_units_Z            3
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    29000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.651
_exptl_crystal_F_000             894
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.339
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9833
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29374
_diffrn_reflns_av_unetI/netI     0.1047
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.850
_diffrn_reflns_theta_max         30.537
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8994
_reflns_number_gt                5542
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0158P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1891 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.031(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8994
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.0645
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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_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 0.80092(2) 0.80092(2) 0.0000 0.02290(11) Uani 1 2 d S T P . .
N1 N 0.73648(12) 0.85143(12) 0.07915(11) 0.0302(4) Uani 1 1 d . . . . .
C1 C 0.70110(15) 0.81181(16) 0.15518(16) 0.0409(6) Uani 1 1 d . . . . .
H1 H 0.6985 0.7600 0.1681 0.049 Uiso 1 1 calc R U . . .
C2 C 0.66836(16) 0.84488(17) 0.21507(16) 0.0457(7) Uani 1 1 d . . . . .
H2 H 0.6455 0.8166 0.2689 0.055 Uiso 1 1 calc R U . . .
C3 C 0.66899(15) 0.91847(17) 0.19657(15) 0.0343(6) Uani 1 1 d . . . . .
C4 C 0.70053(17) 0.95593(17) 0.11729(17) 0.0491(8) Uani 1 1 d . . . . .
H4 H 0.6999 1.0055 0.1008 0.059 Uiso 1 1 calc R U . . .
C5 C 0.73367(17) 0.91968(17) 0.06093(16) 0.0428(7) Uani 1 1 d . . . . .
H5 H 0.7555 0.9462 0.0060 0.051 Uiso 1 1 calc R U . . .
C6 C 1.35498(15) 1.31397(14) 0.06787(14) 0.0387(6) Uani 1 1 d . . . . .
C7 C 1.29599(19) 1.29599(19) 0.0000 0.0404(9) Uani 1 2 d S T P . .
C8 C 1.21810(19) 1.21810(19) 0.0000 0.0474(10) Uani 1 2 d S T P . .
C9 C 1.15333(19) 1.15333(19) 0.0000 0.0467(11) Uani 1 2 d S T P . .
C10 C 1.07465(17) 1.07465(17) 0.0000 0.0398(10) Uani 1 2 d S T P . .
C11 C 1.06472(17) 1.00857(16) 0.05053(18) 0.0529(8) Uani 1 1 d . . . . .
H11 H 1.1095 1.0139 0.0863 0.063 Uiso 1 1 calc R U . . .
C12 C 0.98857(15) 0.93399(15) 0.04870(16) 0.0432(7) Uani 1 1 d . . . . .
H12 H 0.9826 0.8885 0.0836 0.052 Uiso 1 1 calc R U . . .
N2 N 0.92274(14) 0.92274(14) 0.0000 0.0289(7) Uani 1 2 d S T P . .
C13 C 0.43070(14) 0.39004(14) 0.06627(15) 0.0377(6) Uani 1 1 d . . . . .
H13 H 0.4709 0.4022 0.1113 0.045 Uiso 1 1 calc R U . . .
C14 C 0.44818(17) 0.44818(17) 0.0000 0.0335(9) Uani 1 2 d S T P . .
C15 C 0.52733(17) 0.52733(17) 0.0000 0.0322(9) Uani 1 2 d S T P . .
C16 C 0.60337(15) 0.53247(16) 0.02550(15) 0.0388(7) Uani 1 1 d . . . . .
H16 H 0.6044 0.4833 0.0428 0.047 Uiso 1 1 calc R U . . .
C17 C 0.67673(14) 0.60970(14) 0.02523(15) 0.0362(6) Uani 1 1 d . . . . .
H17 H 0.7271 0.6121 0.0442 0.043 Uiso 1 1 calc R U . . .
N3 N 0.68039(14) 0.68039(14) 0.0000 0.0292(7) Uani 1 2 d S T P . .
N4 N 0.84018(12) 0.76333(12) 0.11452(12) 0.0321(4) Uani 1 1 d . . . . .
C18 C 0.85503(17) 0.73753(17) 0.17545(17) 0.0440(6) Uani 1 1 d . . . . .
S1 S 0.87529(9) 0.70319(7) 0.26412(7) 0.1311(5) Uani 1 1 d . . . . .


_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 N4 2.131(2) . ?
Fe1 N4 2.131(2) 6 ?
Fe1 N1 2.1946(17) . ?
Fe1 N1 2.1946(17) 6 ?
Fe1 N3 2.214(3) . ?
Fe1 N2 2.238(3) . ?
N1 C5 1.310(3) . ?
N1 C1 1.350(3) . ?
C1 C2 1.389(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.375(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.368(3) . ?
C3 C6 1.476(3) 5_765 ?
C4 C5 1.399(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C13 1.394(3) 1_665 ?
C6 C7 1.413(3) . ?
C6 C3 1.476(3) 5_765 ?
C7 C6 1.413(3) 6 ?
C7 C8 1.431(5) . ?
C8 C9 1.190(4) . ?
C9 C10 1.445(5) . ?
C10 C11 1.370(3) 6 ?
C10 C11 1.370(3) . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 N2 1.344(3) . ?
C12 H12 0.9500 . ?
N2 C12 1.344(3) 6 ?
C13 C14 1.386(3) . ?
C13 C6 1.394(3) 1_445 ?
C13 H13 0.9500 . ?
C14 C13 1.386(3) 6 ?
C14 C15 1.454(4) . ?
C15 C16 1.407(3) 6 ?
C15 C16 1.407(3) . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 N3 1.323(3) . ?
C17 H17 0.9500 . ?
N3 C17 1.323(3) 6 ?
N4 C18 1.136(3) . ?
C18 S1 1.612(3) . ?

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
N4 Fe1 N4 179.18(11) . 6 ?
N4 Fe1 N1 91.61(7) . . ?
N4 Fe1 N1 88.44(7) 6 . ?
N4 Fe1 N1 88.44(7) . 6 ?
N4 Fe1 N1 91.61(7) 6 6 ?
N1 Fe1 N1 173.32(10) . 6 ?
N4 Fe1 N3 90.41(5) . . ?
N4 Fe1 N3 90.41(5) 6 . ?
N1 Fe1 N3 86.66(5) . . ?
N1 Fe1 N3 86.66(5) 6 . ?
N4 Fe1 N2 89.59(5) . . ?
N4 Fe1 N2 89.59(5) 6 . ?
N1 Fe1 N2 93.34(5) . . ?
N1 Fe1 N2 93.34(5) 6 . ?
N3 Fe1 N2 180.0 . . ?
C5 N1 C1 117.3(2) . . ?
C5 N1 Fe1 125.15(16) . . ?
C1 N1 Fe1 117.39(15) . . ?
N1 C1 C2 121.7(2) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 118.0(2) . . ?
C4 C3 C6 122.2(2) . 5_765 ?
C2 C3 C6 119.5(2) . 5_765 ?
C3 C4 C5 118.6(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 124.1(2) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C13 C6 C7 119.1(2) 1_665 . ?
C13 C6 C3 124.4(2) 1_665 5_765 ?
C7 C6 C3 116.6(2) . 5_765 ?
C6 C7 C6 119.9(3) . 6 ?
C6 C7 C8 120.03(15) . . ?
C6 C7 C8 120.03(15) 6 . ?
C9 C8 C7 180.0(5) . . ?
C8 C9 C10 180.0(5) . . ?
C11 C10 C11 118.8(3) 6 . ?
C11 C10 C9 120.62(16) 6 . ?
C11 C10 C9 120.62(16) . . ?
C10 C11 C12 119.1(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
N2 C12 C11 123.3(2) . . ?
N2 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
C12 N2 C12 116.4(3) 6 . ?
C12 N2 Fe1 121.78(13) 6 . ?
C12 N2 Fe1 121.78(13) . . ?
C14 C13 C6 121.0(2) . 1_445 ?
C14 C13 H13 119.5 . . ?
C6 C13 H13 119.5 1_445 . ?
C13 C14 C13 119.9(3) . 6 ?
C13 C14 C15 120.07(15) . . ?
C13 C14 C15 120.07(15) 6 . ?
C16 C15 C16 116.0(3) 6 . ?
C16 C15 C14 122.01(15) 6 . ?
C16 C15 C14 122.01(15) . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
N3 C17 C16 123.5(3) . . ?
N3 C17 H17 118.2 . . ?
C16 C17 H17 118.2 . . ?
C17 N3 C17 117.9(3) . 6 ?
C17 N3 Fe1 121.07(14) . . ?
C17 N3 Fe1 121.07(14) 6 . ?
C18 N4 Fe1 174.5(2) . . ?
N4 C18 S1 177.8(2) . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.032

_shelxl_version_number           2014/6



