# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3a
_database_code_depnum_ccdc_archive 'CCDC 1987083'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;Department of Chemistry, University of Zurich
Switzerland
;
_audit_update_record             
;
2020-02-28 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;

_audit_creation_date             2019-02-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H25 Fe N3 O2 S'
_chemical_formula_sum            'C23 H25 Fe N3 O2 S'
_chemical_formula_weight         463.37
_chemical_absolute_configuration ad
_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'
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'
S S 0.3331 0.5567 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.83485(14)
_cell_length_b                   17.7768(6)
_cell_length_c                   20.0446(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2079.12(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5414
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      77.0550
_cell_measurement_theta_min      4.9500
_shelx_estimated_absorpt_T_max   0.873
_shelx_estimated_absorpt_T_min   0.465
_exptl_absorpt_coefficient_mu    6.961
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_correction_T_min  0.558
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.16c (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             968
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0107
0 -1 0 0.0117
0 -2 5 0.0403
0 2 -5 0.0403
-2 -1 -5 0.0437
3 5 1 0.0559
2 5 -4 0.0358
-4 2 1 0.0714
4 -2 -1 0.0534
0 -5 -4 0.0293
0 5 4 0.0287

_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02

_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17347
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.489
_diffrn_reflns_theta_min         3.323
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  28.00   0.50    3.00    --  -51.31  19.00  30.00  108
  2  ω    -51.00 -11.00   0.50    6.00    --  -86.25  45.00  60.00   80
  3  ω    -26.00  28.00   0.50    3.00    --  -51.31  19.00-150.00  108
  4  ω    -35.00  -8.00   0.50    6.00    --  -86.25  30.00-180.00   54
  5  ω    -43.00  26.00   0.50    3.00    --  -51.31  38.00-180.00  138
  6  ω   -128.00 -42.00   0.50    3.00    --  -51.31 -41.00  72.00  172
  7  ω     96.00 178.00   0.50    6.00    --  107.75  45.00-180.00  164
  8  ω    135.00 164.00   0.50    6.00    --  107.75  61.00 -90.00   58
  9  ω    112.00 174.00   0.50    6.00    --  107.75  30.00   0.00  124
 10  ω     96.00 178.00   0.50    6.00    --  107.75  45.00-120.00  164
 11  ω     96.00 178.00   0.50    6.00    --  107.75  45.00 -30.00  164
 12  ω     98.00 178.00   0.50    6.00    --  107.75  15.00 -30.00  160
 13  ω     86.00 178.00   0.50    6.00    --  107.75  77.00  90.00  184
 14  ω     82.00 135.00   0.50    6.00    --  107.75 178.00   0.00  106
 15  ω     37.00  71.00   0.50    6.00    --  107.75 -61.00 -30.00   68
 16  ω     52.00 105.00   0.50    6.00    --  107.75 -77.00 -90.00  106
 17  ω     35.00 105.00   0.50    6.00    --  107.75 -77.00 -30.00  140
 18  ω     70.00 104.00   0.50    6.00    --  107.75 -77.00  30.00   68
 19  ω     37.00  71.00   0.50    6.00    --  107.75 -61.00 120.00   68
 20  ω     37.00  71.00   0.50    6.00    --  107.75 -61.00  30.00   68
 21  ω     37.00  71.00   0.50    6.00    --  107.75 -61.00 -90.00   68
 22  ω     42.00  71.00   0.50    6.00    --  107.75 -61.00-180.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1177991000
_diffrn_orient_matrix_UB_12      -0.0655803000
_diffrn_orient_matrix_UB_13      -0.0366069000
_diffrn_orient_matrix_UB_21      -0.0721375000
_diffrn_orient_matrix_UB_22      0.0340084000
_diffrn_orient_matrix_UB_23      -0.0675321000
_diffrn_orient_matrix_UB_31      0.2251376000
_diffrn_orient_matrix_UB_32      0.0452537000
_diffrn_orient_matrix_UB_33      -0.0023348000
_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              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3739
_reflns_number_total             4249

_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 1.171.40.16c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.16c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.16c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 1333 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+1.5369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1265
_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:
 C11(H11A,H11B), C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10),
 C17(H17), C18(H18), C20(H20)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8576(10) 0.1928(5) 0.9108(3) 0.067(2) Uani 1 1 d . . . . .
H1 H 1.012668 0.188319 0.896966 0.080 Uiso 1 1 calc R . . . .
C2 C 0.7267(12) 0.2588(4) 0.9096(3) 0.0528(15) Uani 1 1 d . . . . .
H2 H 0.777123 0.306707 0.894651 0.063 Uiso 1 1 calc R . . . .
C3 C 0.5047(10) 0.2414(3) 0.9347(3) 0.0435(13) Uani 1 1 d . . . . .
H3 H 0.381412 0.275771 0.939888 0.052 Uiso 1 1 calc R . . . .
C4 C 0.5000(11) 0.1640(3) 0.9507(3) 0.0451(13) Uani 1 1 d . . . . .
H4 H 0.372662 0.136999 0.967938 0.054 Uiso 1 1 calc R . . . .
C5 C 0.7202(15) 0.1339(4) 0.9362(3) 0.062(2) Uani 1 1 d . . . . .
H5 H 0.766692 0.083155 0.942460 0.075 Uiso 1 1 calc R . . . .
C6 C 0.5823(9) 0.2167(3) 0.7558(2) 0.0366(11) Uani 1 1 d . . . . .
C7 C 0.3502(9) 0.2074(3) 0.7790(3) 0.0412(12) Uani 1 1 d . . . . .
H7 H 0.237708 0.245926 0.781815 0.049 Uiso 1 1 calc R . . . .
C8 C 0.3185(10) 0.1307(4) 0.7969(3) 0.0452(13) Uani 1 1 d . . . . .
H8 H 0.181390 0.109151 0.813830 0.054 Uiso 1 1 calc R . . . .
C9 C 0.5287(10) 0.0918(4) 0.7851(3) 0.0454(13) Uani 1 1 d . . . . .
H9 H 0.556082 0.039838 0.792708 0.054 Uiso 1 1 calc R . . . .
C10 C 0.6904(10) 0.1448(3) 0.7597(2) 0.0397(12) Uani 1 1 d . . . . .
H10 H 0.844164 0.134045 0.747384 0.048 Uiso 1 1 calc R . . . .
C11 C 0.6884(10) 0.2885(3) 0.7312(2) 0.0414(12) Uani 1 1 d . . . . .
H11A H 0.611606 0.331803 0.752791 0.050 Uiso 1 1 calc R . . . .
H11B H 0.852297 0.289635 0.743939 0.050 Uiso 1 1 calc R . . . .
C12 C 0.8162(10) 0.2574(3) 0.6156(3) 0.0395(12) Uani 1 1 d . . . . .
C13 C 1.1422(10) 0.1801(4) 0.6127(3) 0.0508(14) Uani 1 1 d . . . . .
H13A H 1.207417 0.210149 0.576413 0.076 Uiso 1 1 calc GR . . . .
H13B H 1.059926 0.136884 0.593990 0.076 Uiso 1 1 calc GR . . . .
H13C H 1.265627 0.162164 0.641804 0.076 Uiso 1 1 calc GR . . . .
C14 C 0.4843(10) 0.3369(3) 0.6329(2) 0.0394(12) Uani 1 1 d . . . . .
C15 C 0.2486(10) 0.3888(3) 0.5610(3) 0.0405(12) Uani 1 1 d . . . . .
C16 C 0.1896(10) 0.4066(3) 0.6267(3) 0.0409(12) Uani 1 1 d . . . . .
C17 C -0.0012(10) 0.4520(4) 0.6375(3) 0.0472(13) Uani 1 1 d . . . . .
H17 H -0.048317 0.464267 0.681536 0.057 Uiso 1 1 calc R . . . .
C18 C -0.1219(10) 0.4790(3) 0.5826(3) 0.0463(13) Uani 1 1 d . . . . .
H18 H -0.251422 0.510463 0.589424 0.056 Uiso 1 1 calc R . . . .
C19 C -0.0562(11) 0.4608(3) 0.5177(3) 0.0451(13) Uani 1 1 d . . . . .
C20 C 0.1292(11) 0.4142(4) 0.5056(3) 0.0481(14) Uani 1 1 d . . . . .
H20 H 0.172380 0.400231 0.461596 0.058 Uiso 1 1 calc R . . . .
C21 C -0.0256(11) 0.5029(4) 0.3810(3) 0.0518(15) Uani 1 1 d . . . . .
H21A H 0.034365 0.451388 0.373777 0.062 Uiso 1 1 calc R . . . .
H21B H -0.113155 0.517190 0.340610 0.062 Uiso 1 1 calc R . . . .
C22 C 0.1735(14) 0.5556(4) 0.3883(4) 0.0606(17) Uani 1 1 d . . . . .
H22A H 0.259142 0.542581 0.429293 0.073 Uiso 1 1 calc R . . . .
H22B H 0.114851 0.607542 0.393439 0.073 Uiso 1 1 calc R . . . .
C23 C 0.3351(14) 0.5531(5) 0.3296(4) 0.068(2) Uani 1 1 d . . . . .
H23A H 0.248744 0.561068 0.288249 0.102 Uiso 1 1 calc GR . . . .
H23B H 0.410869 0.503944 0.328004 0.102 Uiso 1 1 calc GR . . . .
H23C H 0.450819 0.592719 0.334359 0.102 Uiso 1 1 calc GR . . . .
Fe1 Fe 0.57752(14) 0.17833(5) 0.85162(4) 0.0364(2) Uani 1 1 d . . . . .
N1 N 0.6678(8) 0.2954(3) 0.6578(2) 0.0377(9) Uani 1 1 d . . . . .
N2 N 0.4407(9) 0.3437(3) 0.5661(2) 0.0443(11) Uani 1 1 d . . . . .
N3 N 0.3436(8) 0.3736(3) 0.6708(2) 0.0413(10) Uani 1 1 d . . . . .
O1 O 0.9853(6) 0.2257(2) 0.65090(19) 0.0433(9) Uani 1 1 d . . . . .
O2 O 0.7967(7) 0.2524(2) 0.55588(17) 0.0472(9) Uani 1 1 d . . . . .
S1 S -0.2220(3) 0.50107(10) 0.45220(8) 0.0533(4) Uani 1 1 d . . . . .
H2A H 0.505(12) 0.314(4) 0.534(4) 0.06(2) Uiso 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
C1 H1 0.9500 . ?
C1 C2 1.400(11) . ?
C1 C5 1.413(12) . ?
C1 Fe1 2.036(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.424(9) . ?
C2 Fe1 2.038(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.412(8) . ?
C3 Fe1 2.052(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.422(10) . ?
C4 Fe1 2.052(5) . ?
C5 H5 0.9500 . ?
C5 Fe1 2.047(6) . ?
C6 C7 1.441(8) . ?
C6 C10 1.427(8) . ?
C6 C11 1.501(8) . ?
C6 Fe1 2.038(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.422(9) . ?
C7 Fe1 2.036(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.428(9) . ?
C8 Fe1 2.050(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.427(8) . ?
C9 Fe1 2.056(6) . ?
C10 H10 0.9500 . ?
C10 Fe1 2.046(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 N1 1.482(6) . ?
C12 N1 1.387(7) . ?
C12 O1 1.339(7) . ?
C12 O2 1.205(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 O1 1.443(7) . ?
C14 N1 1.393(7) . ?
C14 N2 1.367(7) . ?
C14 N3 1.296(7) . ?
C15 C16 1.396(7) . ?
C15 C20 1.387(8) . ?
C15 N2 1.382(7) . ?
C16 C17 1.392(8) . ?
C16 N3 1.391(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.392(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.394(8) . ?
C19 C20 1.384(9) . ?
C19 S1 1.781(6) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.500(10) . ?
C21 S1 1.831(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.508(11) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N2 H2A 0.91(8) . ?

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
C2 C1 H1 125.7 . . ?
C2 C1 C5 108.5(6) . . ?
C2 C1 Fe1 70.0(3) . . ?
C5 C1 H1 125.7 . . ?
C5 C1 Fe1 70.2(4) . . ?
Fe1 C1 H1 125.7 . . ?
C1 C2 H2 126.0 . . ?
C1 C2 C3 107.9(6) . . ?
C1 C2 Fe1 69.8(4) . . ?
C3 C2 H2 126.0 . . ?
C3 C2 Fe1 70.2(4) . . ?
Fe1 C2 H2 125.6 . . ?
C2 C3 H3 126.0 . . ?
C2 C3 Fe1 69.1(3) . . ?
C4 C3 C2 108.0(6) . . ?
C4 C3 H3 126.0 . . ?
C4 C3 Fe1 69.9(3) . . ?
Fe1 C3 H3 126.6 . . ?
C3 C4 H4 126.2 . . ?
C3 C4 C5 107.6(6) . . ?
C3 C4 Fe1 69.9(3) . . ?
C5 C4 H4 126.2 . . ?
C5 C4 Fe1 69.5(3) . . ?
Fe1 C4 H4 126.0 . . ?
C1 C5 C4 107.9(6) . . ?
C1 C5 H5 126.1 . . ?
C1 C5 Fe1 69.3(3) . . ?
C4 C5 H5 126.1 . . ?
C4 C5 Fe1 69.9(3) . . ?
Fe1 C5 H5 126.3 . . ?
C7 C6 C11 126.2(5) . . ?
C7 C6 Fe1 69.2(3) . . ?
C10 C6 C7 107.2(5) . . ?
C10 C6 C11 126.6(5) . . ?
C10 C6 Fe1 69.8(3) . . ?
C11 C6 Fe1 126.8(3) . . ?
C6 C7 H7 125.9 . . ?
C6 C7 Fe1 69.4(3) . . ?
C8 C7 C6 108.3(5) . . ?
C8 C7 H7 125.9 . . ?
C8 C7 Fe1 70.2(3) . . ?
Fe1 C7 H7 126.2 . . ?
C7 C8 H8 125.9 . . ?
C7 C8 C9 108.1(5) . . ?
C7 C8 Fe1 69.1(3) . . ?
C9 C8 H8 125.9 . . ?
C9 C8 Fe1 69.9(3) . . ?
Fe1 C8 H8 126.6 . . ?
C8 C9 H9 126.1 . . ?
C8 C9 Fe1 69.4(3) . . ?
C10 C9 C8 107.9(5) . . ?
C10 C9 H9 126.1 . . ?
C10 C9 Fe1 69.3(3) . . ?
Fe1 C9 H9 126.8 . . ?
C6 C10 H10 125.7 . . ?
C6 C10 Fe1 69.2(3) . . ?
C9 C10 C6 108.6(5) . . ?
C9 C10 H10 125.7 . . ?
C9 C10 Fe1 70.0(3) . . ?
Fe1 C10 H10 126.6 . . ?
C6 C11 H11A 109.4 . . ?
C6 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N1 C11 C6 111.3(4) . . ?
N1 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
O1 C12 N1 110.0(4) . . ?
O2 C12 N1 125.7(5) . . ?
O2 C12 O1 124.3(5) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
N2 C14 N1 122.8(5) . . ?
N3 C14 N1 122.9(5) . . ?
N3 C14 N2 114.3(5) . . ?
C20 C15 C16 123.9(5) . . ?
N2 C15 C16 105.2(5) . . ?
N2 C15 C20 130.9(5) . . ?
C17 C16 C15 118.4(5) . . ?
N3 C16 C15 110.2(5) . . ?
N3 C16 C17 131.4(5) . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.8(5) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.2(5) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 S1 116.4(5) . . ?
C20 C19 C18 121.2(5) . . ?
C20 C19 S1 122.4(5) . . ?
C15 C20 H20 121.7 . . ?
C19 C20 C15 116.5(5) . . ?
C19 C20 H20 121.7 . . ?
H21A C21 H21B 107.5 . . ?
C22 C21 H21A 108.6 . . ?
C22 C21 H21B 108.6 . . ?
C22 C21 S1 114.8(5) . . ?
S1 C21 H21A 108.6 . . ?
S1 C21 H21B 108.6 . . ?
C21 C22 H22A 109.0 . . ?
C21 C22 H22B 109.0 . . ?
C21 C22 C23 112.9(6) . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 Fe1 C2 40.2(3) . . ?
C1 Fe1 C3 67.9(3) . . ?
C1 Fe1 C4 68.2(3) . . ?
C1 Fe1 C5 40.5(3) . . ?
C1 Fe1 C6 119.7(3) . . ?
C1 Fe1 C7 155.2(3) . . ?
C1 Fe1 C8 162.9(3) . . ?
C1 Fe1 C9 125.7(3) . . ?
C1 Fe1 C10 107.7(2) . . ?
C2 Fe1 C3 40.7(3) . . ?
C2 Fe1 C4 68.2(2) . . ?
C2 Fe1 C5 68.0(3) . . ?
C2 Fe1 C8 155.4(3) . . ?
C2 Fe1 C9 162.6(3) . . ?
C2 Fe1 C10 125.5(3) . . ?
C3 Fe1 C9 155.0(2) . . ?
C4 Fe1 C3 40.2(2) . . ?
C4 Fe1 C9 120.3(2) . . ?
C5 Fe1 C3 67.8(3) . . ?
C5 Fe1 C4 40.6(3) . . ?
C5 Fe1 C8 125.7(3) . . ?
C5 Fe1 C9 107.8(3) . . ?
C6 Fe1 C2 107.3(2) . . ?
C6 Fe1 C3 125.8(2) . . ?
C6 Fe1 C4 163.0(2) . . ?
C6 Fe1 C5 154.7(3) . . ?
C6 Fe1 C8 69.2(2) . . ?
C6 Fe1 C9 69.0(2) . . ?
C6 Fe1 C10 40.9(2) . . ?
C7 Fe1 C2 120.5(3) . . ?
C7 Fe1 C3 107.9(2) . . ?
C7 Fe1 C4 125.4(2) . . ?
C7 Fe1 C5 162.7(3) . . ?
C7 Fe1 C6 41.4(2) . . ?
C7 Fe1 C8 40.7(2) . . ?
C7 Fe1 C9 68.6(2) . . ?
C7 Fe1 C10 68.9(2) . . ?
C8 Fe1 C3 120.5(2) . . ?
C8 Fe1 C4 107.7(2) . . ?
C8 Fe1 C9 40.7(2) . . ?
C10 Fe1 C3 163.1(2) . . ?
C10 Fe1 C4 155.0(2) . . ?
C10 Fe1 C5 120.2(2) . . ?
C10 Fe1 C8 68.6(2) . . ?
C10 Fe1 C9 40.7(2) . . ?
C12 N1 C11 121.0(5) . . ?
C12 N1 C14 121.2(4) . . ?
C14 N1 C11 117.6(4) . . ?
C14 N2 C15 106.0(5) . . ?
C14 N2 H2A 124(5) . . ?
C15 N2 H2A 128(5) . . ?
C14 N3 C16 104.4(4) . . ?
C12 O1 C13 115.1(4) . . ?
C19 S1 C21 104.0(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2A O2 0.91(8) 2.47(7) 3.100(6) 126(6) 4_456 yes

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
C1 C2 C3 C4 -0.6(6) . . . . ?
C1 C2 C3 Fe1 -59.9(4) . . . . ?
C2 C1 C5 C4 0.2(6) . . . . ?
C2 C1 C5 Fe1 59.7(4) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C2 C3 C4 Fe1 -58.7(4) . . . . ?
C3 C4 C5 C1 -0.6(6) . . . . ?
C3 C4 C5 Fe1 -59.7(4) . . . . ?
C5 C1 C2 C3 0.3(6) . . . . ?
C5 C1 C2 Fe1 -59.8(4) . . . . ?
C6 C7 C8 C9 -0.1(6) . . . . ?
C6 C7 C8 Fe1 59.1(3) . . . . ?
C6 C11 N1 C12 -79.6(6) . . . . ?
C6 C11 N1 C14 95.7(6) . . . . ?
C7 C6 C10 C9 -0.2(5) . . . . ?
C7 C6 C10 Fe1 -59.4(3) . . . . ?
C7 C6 C11 N1 -93.0(6) . . . . ?
C7 C8 C9 C10 0.0(6) . . . . ?
C7 C8 C9 Fe1 58.7(4) . . . . ?
C8 C9 C10 C6 0.2(6) . . . . ?
C8 C9 C10 Fe1 58.9(4) . . . . ?
C10 C6 C7 C8 0.2(5) . . . . ?
C10 C6 C7 Fe1 59.8(3) . . . . ?
C10 C6 C11 N1 86.0(6) . . . . ?
C11 C6 C7 C8 179.3(5) . . . . ?
C11 C6 C7 Fe1 -121.1(5) . . . . ?
C11 C6 C10 C9 -179.3(5) . . . . ?
C11 C6 C10 Fe1 121.5(5) . . . . ?
C15 C16 C17 C18 -1.5(9) . . . . ?
C15 C16 N3 C14 -1.1(7) . . . . ?
C16 C15 C20 C19 1.1(9) . . . . ?
C16 C15 N2 C14 0.3(6) . . . . ?
C16 C17 C18 C19 0.7(9) . . . . ?
C17 C16 N3 C14 179.1(6) . . . . ?
C17 C18 C19 C20 1.1(10) . . . . ?
C17 C18 C19 S1 -178.6(5) . . . . ?
C18 C19 C20 C15 -1.9(9) . . . . ?
C18 C19 S1 C21 155.1(5) . . . . ?
C20 C15 C16 C17 0.6(9) . . . . ?
C20 C15 C16 N3 -179.2(6) . . . . ?
C20 C15 N2 C14 180.0(6) . . . . ?
C20 C19 S1 C21 -24.6(6) . . . . ?
C22 C21 S1 C19 -67.1(5) . . . . ?
Fe1 C1 C2 C3 60.1(4) . . . . ?
Fe1 C1 C5 C4 -59.5(4) . . . . ?
Fe1 C2 C3 C4 59.2(4) . . . . ?
Fe1 C3 C4 C5 59.5(4) . . . . ?
Fe1 C4 C5 C1 59.1(4) . . . . ?
Fe1 C6 C7 C8 -59.6(4) . . . . ?
Fe1 C6 C10 C9 59.2(4) . . . . ?
Fe1 C6 C11 N1 177.1(4) . . . . ?
Fe1 C7 C8 C9 -59.2(4) . . . . ?
Fe1 C8 C9 C10 -58.8(4) . . . . ?
Fe1 C9 C10 C6 -58.7(3) . . . . ?
N1 C12 O1 C13 175.9(5) . . . . ?
N1 C14 N2 C15 -179.6(5) . . . . ?
N1 C14 N3 C16 179.8(5) . . . . ?
N2 C14 N1 C11 -176.3(5) . . . . ?
N2 C14 N1 C12 -1.0(8) . . . . ?
N2 C14 N3 C16 1.4(7) . . . . ?
N2 C15 C16 C17 -179.7(5) . . . . ?
N2 C15 C16 N3 0.5(7) . . . . ?
N2 C15 C20 C19 -178.5(6) . . . . ?
N3 C14 N1 C11 5.3(8) . . . . ?
N3 C14 N1 C12 -179.4(5) . . . . ?
N3 C14 N2 C15 -1.1(7) . . . . ?
N3 C16 C17 C18 178.3(6) . . . . ?
O1 C12 N1 C11 -8.5(7) . . . . ?
O1 C12 N1 C14 176.3(5) . . . . ?
O2 C12 N1 C11 170.7(6) . . . . ?
O2 C12 N1 C14 -4.5(9) . . . . ?
O2 C12 O1 C13 -3.3(8) . . . . ?
S1 C19 C20 C15 177.7(5) . . . . ?
S1 C21 C22 C23 177.9(5) . . . . ?

_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.381
_oxdiff_exptl_absorpt_empirical_full_min 0.723
####################################################################### 
# 
# 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_3h
_database_code_depnum_ccdc_archive 'CCDC 1987085'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;Department of Chemistry, University of Zurich
Switzerland
;
_audit_update_record             
;
2020-02-28 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;

_audit_creation_date             2019-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H25 N3 O2 Ru S'
_chemical_formula_sum            'C23 H25 N3 O2 Ru S'
_chemical_formula_weight         508.59
_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'
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'
Ru Ru 0.0552 3.2960 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   14.3677(5)
_cell_length_b                   5.7086(2)
_cell_length_c                   24.4132(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.675(3)
_cell_angle_gamma                90
_cell_volume                     1984.42(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9140
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      75.6460
_cell_measurement_theta_min      3.6430
_shelx_estimated_absorpt_T_max   0.863
_shelx_estimated_absorpt_T_min   0.298
_exptl_absorpt_coefficient_mu    7.595
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.457
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0077
1 0 1 0.0138
-1 0 -1 0.0069
0 0 1 0.0182
0 0 -1 0.0122
1 -1 0 0.0965
-1 1 0 0.0904
-1 0 2 0.0175
0 -1 -5 0.0584

_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02

_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            22576
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.388
_diffrn_reflns_theta_min         3.104
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  18.00   0.60    3.50    --  -54.70  57.00 -60.00  140
  2  ω    -51.00  -9.00   0.60    6.00    --  -84.25  45.00  90.00   70
  3  ω    -35.00  -7.40   0.60    6.00    --  -84.25  30.00 120.00   46
  4  ω   -129.00 -71.40   0.60    3.50    --  -54.70-125.00-120.00   96
  5  ω   -127.00 -35.80   0.60    3.50    --  -54.70 -72.00-173.00  152
  6  ω   -127.00 -41.80   0.60    3.50    --  -54.70 -57.00   0.00  142
  7  ω     91.00 178.00   0.60    6.00    --  100.44  30.00  60.00  145
  8  ω     99.00 177.00   0.60    6.00    --  100.44 111.00   0.00  130
  9  ω     85.00 170.20   0.60    6.00    --  100.44  61.00 -60.00  142
 10  ω     91.00 178.00   0.60    6.00    --  100.44  30.00 -90.00  145
 11  ω     30.00  69.60   0.60    6.00    --  100.44 -61.00 -90.00   66
 12  ω     28.00 103.60   0.60    6.00    --  100.44 -77.00-150.00  126
 13  ω     30.00  69.60   0.60    6.00    --  100.44 -61.00   0.00   66
 14  ω     30.00  69.60   0.60    6.00    --  100.44 -61.00 -30.00   66
 15  ω     30.00  69.60   0.60    6.00    --  100.44 -61.00-120.00   66
 16  ω     30.00  69.60   0.60    6.00    --  100.44 -61.00-150.00   66
 17  ω     25.00  49.60   0.60    6.00    --  100.44 -45.00  90.00   41
 18  ω     25.00  49.60   0.60    6.00    --  100.44 -45.00 150.00   41
 19  ω     30.00  69.60   0.60    6.00    --  100.44 -61.00 150.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1044035000
_diffrn_orient_matrix_UB_12      0.0689524000
_diffrn_orient_matrix_UB_13      0.0045794000
_diffrn_orient_matrix_UB_21      -0.0256702000
_diffrn_orient_matrix_UB_22      0.2055194000
_diffrn_orient_matrix_UB_23      -0.0400839000
_diffrn_orient_matrix_UB_31      -0.0118584000
_diffrn_orient_matrix_UB_32      0.1607161000
_diffrn_orient_matrix_UB_33      0.0492902000
_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              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                19706
_reflns_number_total             22576
_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 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         22576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0765
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5358(8)
 0.4642(8)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C21(H21A,H21B), C22(H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10),
 C16(H16), C17(H17), C19(H19)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8131(3) 1.1559(8) 0.72096(15) 0.0256(9) Uani 1 1 d . . . . .
H1 H 0.753394 1.160702 0.733642 0.031 Uiso 1 1 calc R . . . .
C2 C 0.8544(3) 1.3395(8) 0.69439(15) 0.0308(10) Uani 1 1 d . . . . .
H2 H 0.827628 1.489461 0.685928 0.037 Uiso 1 1 calc R . . . .
C3 C 0.9429(3) 1.2615(10) 0.68251(18) 0.0399(13) Uani 1 1 d . . . . .
H3 H 0.986122 1.350036 0.664711 0.048 Uiso 1 1 calc R . . . .
C4 C 0.9559(3) 1.0278(10) 0.70180(17) 0.0363(12) Uani 1 1 d . . . . .
H4 H 1.009226 0.932156 0.699184 0.044 Uiso 1 1 calc R . . . .
C5 C 0.8752(3) 0.9627(8) 0.72562(15) 0.0265(9) Uani 1 1 d . . . . .
H5 H 0.864687 0.815511 0.741860 0.032 Uiso 1 1 calc R . . . .
C6 C 0.7088(3) 1.0363(7) 0.57573(14) 0.0169(8) Uani 1 1 d . . . . .
C7 C 0.7849(3) 1.1430(7) 0.55249(15) 0.0191(8) Uani 1 1 d . . . . .
H7 H 0.786144 1.298749 0.538872 0.023 Uiso 1 1 calc R . . . .
C8 C 0.8586(3) 0.9743(7) 0.55338(15) 0.0230(9) Uani 1 1 d . . . . .
H8 H 0.917264 0.997922 0.540357 0.028 Uiso 1 1 calc R . . . .
C9 C 0.8285(3) 0.7652(7) 0.57718(15) 0.0220(8) Uani 1 1 d . . . . .
H9 H 0.863857 0.624697 0.583086 0.026 Uiso 1 1 calc R . . . .
C10 C 0.7362(3) 0.8021(7) 0.59067(14) 0.0194(8) Uani 1 1 d . . . . .
H10 H 0.699221 0.690111 0.606826 0.023 Uiso 1 1 calc R . . . .
C11 C 0.6144(3) 1.1515(7) 0.57572(14) 0.0183(8) Uani 1 1 d . . . . .
H11A H 0.622848 1.323642 0.575714 0.022 Uiso 1 1 calc R . . . .
H11B H 0.573608 1.108576 0.541263 0.022 Uiso 1 1 calc R . . . .
C12 C 0.5766(3) 1.2115(7) 0.67174(15) 0.0189(8) Uani 1 1 d . . . . .
C13 C 0.6364(3) 1.5572(7) 0.71612(15) 0.0238(9) Uani 1 1 d . . . . .
H13A H 0.667426 1.703631 0.708015 0.036 Uiso 1 1 calc GR . . . .
H13B H 0.675682 1.473015 0.745623 0.036 Uiso 1 1 calc GR . . . .
H13C H 0.575402 1.592582 0.728021 0.036 Uiso 1 1 calc GR . . . .
C14 C 0.5076(2) 0.8879(7) 0.61636(15) 0.0179(8) Uani 1 1 d . . . . .
C15 C 0.4321(3) 0.5932(7) 0.58004(15) 0.0196(8) Uani 1 1 d . . . . .
C16 C 0.3933(3) 0.4130(7) 0.54614(15) 0.0215(8) Uani 1 1 d . . . . .
H16 H 0.409918 0.393190 0.510039 0.026 Uiso 1 1 calc R . . . .
C17 C 0.3299(3) 0.2627(7) 0.56615(16) 0.0222(9) Uani 1 1 d . . . . .
H17 H 0.302281 0.140073 0.543159 0.027 Uiso 1 1 calc R . . . .
C18 C 0.3056(3) 0.2880(7) 0.61974(16) 0.0197(8) Uani 1 1 d . . . . .
C19 C 0.3442(3) 0.4668(7) 0.65441(15) 0.0211(8) Uani 1 1 d . . . . .
H19 H 0.328654 0.484567 0.690799 0.025 Uiso 1 1 calc R . . . .
C20 C 0.4064(3) 0.6177(7) 0.63344(15) 0.0185(8) Uani 1 1 d . . . . .
C21 C 0.1855(3) -0.0960(7) 0.59122(16) 0.0230(9) Uani 1 1 d . . . . .
H21A H 0.157186 -0.005081 0.558662 0.028 Uiso 1 1 calc R . . . .
H21B H 0.239804 -0.183944 0.580736 0.028 Uiso 1 1 calc R . . . .
C22 C 0.1133(3) -0.2669(8) 0.60848(18) 0.0266(9) Uani 1 1 d . . . . .
H22A H 0.141298 -0.355117 0.641538 0.032 Uiso 1 1 calc R . . . .
H22B H 0.058563 -0.178731 0.618323 0.032 Uiso 1 1 calc R . . . .
C23 C 0.0811(3) -0.4371(8) 0.56201(17) 0.0309(10) Uani 1 1 d . . . . .
H23A H 0.051584 -0.350091 0.529668 0.046 Uiso 1 1 calc GR . . . .
H23B H 0.035498 -0.546932 0.574125 0.046 Uiso 1 1 calc GR . . . .
H23C H 0.135265 -0.524263 0.552252 0.046 Uiso 1 1 calc GR . . . .
N1 N 0.5666(2) 1.0850(5) 0.62375(12) 0.0177(7) Uani 1 1 d . . . . .
N2 N 0.4967(2) 0.7660(6) 0.57059(12) 0.0192(7) Uani 1 1 d . . . . .
N3 N 0.4555(2) 0.8110(6) 0.65560(14) 0.0197(7) Uani 1 1 d . . . . .
H3A H 0.457(3) 0.869(8) 0.685(2) 0.027(13) Uiso 1 1 d . . . . .
O1 O 0.62239(18) 1.4125(5) 0.66669(10) 0.0203(6) Uani 1 1 d . . . . .
O2 O 0.54860(19) 1.1508(5) 0.71456(11) 0.0247(6) Uani 1 1 d . . . . .
Ru1 Ru 0.83447(2) 1.04481(5) 0.63779(2) 0.01688(10) Uani 1 1 d . . . . .
S1 S 0.22456(7) 0.10099(19) 0.64745(4) 0.0263(2) 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
C1 H1 0.9500 . ?
C1 C2 1.405(6) . ?
C1 C5 1.414(6) . ?
C1 Ru1 2.188(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.413(7) . ?
C2 Ru1 2.172(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.419(7) . ?
C3 Ru1 2.167(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.414(6) . ?
C4 Ru1 2.183(4) . ?
C5 H5 0.9500 . ?
C5 Ru1 2.197(4) . ?
C6 C7 1.433(5) . ?
C6 C10 1.427(6) . ?
C6 C11 1.507(5) . ?
C6 Ru1 2.197(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.429(6) . ?
C7 Ru1 2.182(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.420(6) . ?
C8 Ru1 2.172(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.424(6) . ?
C9 Ru1 2.171(4) . ?
C10 H10 0.9500 . ?
C10 Ru1 2.192(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 N1 1.486(4) . ?
C12 N1 1.367(5) . ?
C12 O1 1.336(5) . ?
C12 O2 1.220(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 O1 1.454(4) . ?
C14 N1 1.405(5) . ?
C14 N2 1.308(5) . ?
C14 N3 1.365(5) . ?
C15 C16 1.389(6) . ?
C15 C20 1.408(5) . ?
C15 N2 1.395(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.406(5) . ?
C18 C19 1.393(6) . ?
C18 S1 1.778(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(6) . ?
C20 N3 1.381(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.523(6) . ?
C21 S1 1.805(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.518(6) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N3 H3A 0.79(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 125.8 . . ?
C2 C1 C5 108.5(4) . . ?
C2 C1 Ru1 70.6(2) . . ?
C5 C1 H1 125.8 . . ?
C5 C1 Ru1 71.5(2) . . ?
Ru1 C1 H1 123.8 . . ?
C1 C2 H2 126.1 . . ?
C1 C2 C3 107.9(4) . . ?
C1 C2 Ru1 71.8(2) . . ?
C3 C2 H2 126.1 . . ?
C3 C2 Ru1 70.8(3) . . ?
Ru1 C2 H2 123.0 . . ?
C2 C3 H3 126.0 . . ?
C2 C3 C4 108.1(4) . . ?
C2 C3 Ru1 71.2(2) . . ?
C4 C3 H3 126.0 . . ?
C4 C3 Ru1 71.6(3) . . ?
Ru1 C3 H3 122.9 . . ?
C3 C4 H4 126.1 . . ?
C3 C4 Ru1 70.3(2) . . ?
C5 C4 C3 107.7(4) . . ?
C5 C4 H4 126.1 . . ?
C5 C4 Ru1 71.7(2) . . ?
Ru1 C4 H4 123.5 . . ?
C1 C5 H5 126.1 . . ?
C1 C5 Ru1 70.8(2) . . ?
C4 C5 C1 107.8(4) . . ?
C4 C5 H5 126.1 . . ?
C4 C5 Ru1 70.7(2) . . ?
Ru1 C5 H5 124.0 . . ?
C7 C6 C11 123.3(3) . . ?
C7 C6 Ru1 70.3(2) . . ?
C10 C6 C7 107.5(3) . . ?
C10 C6 C11 128.8(3) . . ?
C10 C6 Ru1 70.8(2) . . ?
C11 C6 Ru1 130.3(2) . . ?
C6 C7 H7 126.0 . . ?
C6 C7 Ru1 71.5(2) . . ?
C8 C7 C6 108.1(3) . . ?
C8 C7 H7 126.0 . . ?
C8 C7 Ru1 70.5(2) . . ?
Ru1 C7 H7 123.7 . . ?
C7 C8 H8 126.0 . . ?
C7 C8 Ru1 71.2(2) . . ?
C9 C8 C7 107.9(3) . . ?
C9 C8 H8 126.0 . . ?
C9 C8 Ru1 70.8(2) . . ?
Ru1 C8 H8 123.5 . . ?
C8 C9 H9 125.9 . . ?
C8 C9 C10 108.3(4) . . ?
C8 C9 Ru1 71.0(2) . . ?
C10 C9 H9 125.9 . . ?
C10 C9 Ru1 71.8(2) . . ?
Ru1 C9 H9 123.1 . . ?
C6 C10 H10 125.9 . . ?
C6 C10 Ru1 71.2(2) . . ?
C9 C10 C6 108.2(3) . . ?
C9 C10 H10 125.9 . . ?
C9 C10 Ru1 70.2(2) . . ?
Ru1 C10 H10 124.4 . . ?
C6 C11 H11A 108.9 . . ?
C6 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
N1 C11 C6 113.6(3) . . ?
N1 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
O1 C12 N1 111.8(3) . . ?
O2 C12 N1 125.1(4) . . ?
O2 C12 O1 123.1(4) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
N2 C14 N1 122.5(3) . . ?
N2 C14 N3 114.5(3) . . ?
N3 C14 N1 123.0(3) . . ?
C16 C15 C20 119.4(4) . . ?
C16 C15 N2 130.4(3) . . ?
N2 C15 C20 110.2(3) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 118.6(3) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.4(4) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 S1 123.3(3) . . ?
C19 C18 C17 120.8(4) . . ?
C19 C18 S1 115.9(3) . . ?
C18 C19 H19 121.5 . . ?
C20 C19 C18 117.1(3) . . ?
C20 C19 H19 121.5 . . ?
C19 C20 C15 122.8(4) . . ?
N3 C20 C15 105.0(3) . . ?
N3 C20 C19 132.2(3) . . ?
H21A C21 H21B 108.2 . . ?
C22 C21 H21A 109.7 . . ?
C22 C21 H21B 109.7 . . ?
C22 C21 S1 110.0(3) . . ?
S1 C21 H21A 109.7 . . ?
S1 C21 H21B 109.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C23 C22 C21 110.7(3) . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C12 N1 C11 122.3(3) . . ?
C12 N1 C14 121.7(3) . . ?
C14 N1 C11 116.0(3) . . ?
C14 N2 C15 104.0(3) . . ?
C14 N3 C20 106.3(3) . . ?
C14 N3 H3A 123(4) . . ?
C20 N3 H3A 130(3) . . ?
C12 O1 C13 115.2(3) . . ?
C1 Ru1 C5 37.63(15) . . ?
C1 Ru1 C6 116.23(14) . . ?
C1 Ru1 C10 120.65(15) . . ?
C2 Ru1 C1 37.61(16) . . ?
C2 Ru1 C4 63.52(18) . . ?
C2 Ru1 C5 63.17(16) . . ?
C2 Ru1 C6 118.84(16) . . ?
C2 Ru1 C7 114.00(15) . . ?
C2 Ru1 C8 136.30(16) . . ?
C2 Ru1 C10 147.65(16) . . ?
C3 Ru1 C1 63.10(17) . . ?
C3 Ru1 C2 38.02(19) . . ?
C3 Ru1 C4 38.07(19) . . ?
C3 Ru1 C5 63.24(17) . . ?
C3 Ru1 C6 146.04(18) . . ?
C3 Ru1 C7 117.09(17) . . ?
C3 Ru1 C8 112.89(16) . . ?
C3 Ru1 C9 136.37(18) . . ?
C3 Ru1 C10 174.21(18) . . ?
C4 Ru1 C1 63.03(15) . . ?
C4 Ru1 C5 37.66(17) . . ?
C4 Ru1 C6 175.64(18) . . ?
C4 Ru1 C10 138.14(18) . . ?
C5 Ru1 C6 139.11(15) . . ?
C7 Ru1 C1 137.97(16) . . ?
C7 Ru1 C4 145.31(16) . . ?
C7 Ru1 C5 175.45(15) . . ?
C7 Ru1 C6 38.20(14) . . ?
C7 Ru1 C10 63.66(14) . . ?
C8 Ru1 C1 173.77(16) . . ?
C8 Ru1 C4 117.23(15) . . ?
C8 Ru1 C5 146.21(16) . . ?
C8 Ru1 C6 64.02(14) . . ?
C8 Ru1 C7 38.31(15) . . ?
C8 Ru1 C10 63.77(14) . . ?
C9 Ru1 C1 148.01(16) . . ?
C9 Ru1 C2 173.41(16) . . ?
C9 Ru1 C4 114.23(17) . . ?
C9 Ru1 C5 119.32(16) . . ?
C9 Ru1 C6 63.87(14) . . ?
C9 Ru1 C7 63.92(15) . . ?
C9 Ru1 C8 38.18(15) . . ?
C9 Ru1 C10 38.10(15) . . ?
C10 Ru1 C5 116.53(15) . . ?
C10 Ru1 C6 37.97(15) . . ?
C18 S1 C21 103.75(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H10 O1 0.95 2.51 3.446(5) 168.7 1_545 yes
C13 H13C O2 0.98 2.43 3.378(5) 162.1 2_656 yes
N3 H3A O2 0.79(5) 2.14(5) 2.667(4) 125(4) . yes

_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 1.422
_oxdiff_exptl_absorpt_empirical_full_min 0.652
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5358(8) 7850 6848 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.4642(8) 7878 6848 nmt -1.0003 -0.0004 -0.1566 0.0000 -0.9999 -0.0000 0.0008
0.0006 1.0001

_twin_special_details            
;
Component 2 rotated by 179.9961° 
 around [-0.08 -0.00 1.00] (reciprocal) or [0.00 0.00 1.00] (direct)
;
####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 1987084'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;Department of Chemistry, University of Zurich
Switzerland
;
_audit_update_record             
;
2020-02-28 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;

_audit_creation_date             2018-12-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'to be completed'
_chemical_formula_moiety         'C25 H27 Fe N3 O2 S'
_chemical_formula_sum            'C25 H27 Fe N3 O2 S'
_chemical_formula_weight         489.40
_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'
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'
S S 0.3331 0.5567 '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                   16.3901(5)
_cell_length_b                   5.60261(16)
_cell_length_c                   23.9440(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.292(3)
_cell_angle_gamma                90
_cell_volume                     2196.96(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3639
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      77.4
_cell_measurement_theta_min      4.5
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.458
_exptl_absorpt_coefficient_mu    6.620
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0075
1 0 0 0.0045
0 0 -1 0.0181
0 0 1 0.0181
-1 -4 -1 0.0699
1 4 1 0.0699

_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01

_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0828
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16361
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.454
_diffrn_reflns_theta_min         3.695
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -75.00   8.00   0.50   13.00    --    0.00 -43.00  43.84  166
  2  ω     -9.00  31.00   0.50   13.00    --    0.00 -98.00  39.23   80
  3  ω    -77.00   8.00   0.50   13.00    --    0.00   0.00  60.00  170
  4  ω    -79.00   6.00   0.50   13.00    --    0.00 -19.00 -60.00  170
  5  ω    -77.00   1.00   0.50   13.00    --    0.00 -38.00-120.00  156
  6  ω    -77.00  -9.00   0.50   32.00    --  -84.25  45.00 -30.00  136
  7  ω    -79.00   6.00   0.50   13.00    --    0.00 -19.00 150.00  170
  8  ω     27.00  69.00   0.50   32.00    --  104.08 -30.00  60.00   84
  9  ω     34.00 118.00   0.50   32.00    --  104.08 -61.00 120.00  168
 10  ω     28.00 113.00   0.50   32.00    --  104.08-112.00  20.00  170
 11  ω     32.00 124.00   0.50   32.00    --  104.08 -77.00  60.00  184
 12  ω     29.00  77.00   0.50   32.00    --  104.08 -45.00  30.00   96
 13  ω     27.00  69.00   0.50   32.00    --  104.08 -30.00  90.00   84
 14  ω     28.00 109.00   0.50   32.00    --  104.08 -94.00  60.00  162
 15  ω     27.00  69.00   0.50   32.00    --  104.08 -30.00 -90.00   84
 16  ω     27.00  69.00   0.50   32.00    --  104.08 -30.00-150.00   84
 17  ω     27.00  69.00   0.50   32.00    --  104.08 -30.00-120.00   84
 18  ω     27.00  69.00   0.50   32.00    --  104.08 -30.00-180.00   84
 19  ω     27.00 103.50   0.50   32.00    --  104.08   0.00-120.00  153
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0855893000
_diffrn_orient_matrix_UB_12      0.1089081000
_diffrn_orient_matrix_UB_13      0.0104793000
_diffrn_orient_matrix_UB_21      -0.0387381000
_diffrn_orient_matrix_UB_22      0.2472000000
_diffrn_orient_matrix_UB_23      0.0086010000
_diffrn_orient_matrix_UB_31      -0.0050699000
_diffrn_orient_matrix_UB_32      -0.0516587000
_diffrn_orient_matrix_UB_33      0.0629264000
_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              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2835
_reflns_number_total             4423

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4423
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0595
_refine_ls_restrained_S_all      1.018
_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)+(0.0660P)²+1.7581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1563
_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. Restrained distances
 N2-H2A
 0.87 with sigma of 0.005
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C23(H23A,H23B), C24(H24A,H24B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11), C12(H12), C19(H19), C20(H20), C22(H22)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2152(3) 0.8374(8) 0.42556(17) 0.0327(10) Uani 1 1 d . . . . .
C2 C 0.1514(3) 0.9791(9) 0.44681(17) 0.0352(10) Uani 1 1 d . . . . .
H2 H 0.156155 1.139825 0.459168 0.042 Uiso 1 1 calc R . . . .
C3 C 0.0789(3) 0.8372(9) 0.44630(18) 0.0400(11) Uani 1 1 d . . . . .
H3 H 0.026937 0.887372 0.458006 0.048 Uiso 1 1 calc R . . . .
C4 C 0.0982(3) 0.6084(9) 0.42524(19) 0.0390(11) Uani 1 1 d . . . . .
H4 H 0.061728 0.477586 0.420644 0.047 Uiso 1 1 calc R . . . .
C5 C 0.1819(3) 0.6102(8) 0.41228(18) 0.0363(10) Uani 1 1 d . . . . .
H5 H 0.210830 0.480029 0.397134 0.044 Uiso 1 1 calc R . . . .
C6 C 0.1635(3) 1.0094(10) 0.29540(19) 0.0468(13) Uani 1 1 d . . . . .
H6 H 0.218772 1.049821 0.289526 0.056 Uiso 1 1 calc R . . . .
C7 C 0.1044(3) 1.1606(10) 0.3172(2) 0.0484(13) Uani 1 1 d . . . . .
H7 H 0.112663 1.321204 0.328801 0.058 Uiso 1 1 calc R . . . .
C8 C 0.0298(3) 1.0310(10) 0.31892(19) 0.0446(12) Uani 1 1 d . . . . .
H8 H -0.020442 1.090312 0.331638 0.053 Uiso 1 1 calc R . . . .
C9 C 0.0438(3) 0.7973(9) 0.29825(19) 0.0415(12) Uani 1 1 d . . . . .
H9 H 0.004900 0.671902 0.294846 0.050 Uiso 1 1 calc R . . . .
C10 C 0.1263(3) 0.7864(9) 0.28373(19) 0.0445(12) Uani 1 1 d . . . . .
H10 H 0.152604 0.651328 0.268577 0.053 Uiso 1 1 calc R . . . .
C11 C 0.2994(3) 0.9096(8) 0.41701(17) 0.0333(10) Uani 1 1 d . . . . .
H11 H 0.329777 0.815445 0.392227 0.040 Uiso 1 1 calc R . . . .
C12 C 0.3370(3) 1.0946(8) 0.44078(16) 0.0321(10) Uani 1 1 d . . . . .
H12 H 0.306742 1.187819 0.465858 0.038 Uiso 1 1 calc R . . . .
C13 C 0.4234(3) 1.1703(8) 0.43155(16) 0.0320(10) Uani 1 1 d . . . . .
H13A H 0.425880 1.346739 0.430383 0.038 Uiso 1 1 calc R . . . .
H13B H 0.458776 1.115887 0.463529 0.038 Uiso 1 1 calc R . . . .
C14 C 0.4355(3) 1.1784(8) 0.32889(17) 0.0342(10) Uani 1 1 d . . . . .
C15 C 0.3587(3) 1.4856(9) 0.28557(19) 0.0444(12) Uani 1 1 d . . . . .
H15A H 0.332127 1.369353 0.260258 0.067 Uiso 1 1 calc GR . . . .
H15B H 0.405393 1.557067 0.267435 0.067 Uiso 1 1 calc GR . . . .
H15C H 0.319638 1.610904 0.294552 0.067 Uiso 1 1 calc GR . . . .
C16 C 0.5042(2) 0.8724(8) 0.38358(16) 0.0309(9) Uani 1 1 d . . . . .
C17 C 0.5882(3) 0.5813(8) 0.36133(17) 0.0316(10) Uani 1 1 d . . . . .
C18 C 0.5726(3) 0.5795(8) 0.41858(17) 0.0323(10) Uani 1 1 d . . . . .
C19 C 0.6095(3) 0.4071(8) 0.45303(18) 0.0363(11) Uani 1 1 d . . . . .
H19 H 0.598533 0.400581 0.491657 0.044 Uiso 1 1 calc R . . . .
C20 C 0.6623(3) 0.2456(9) 0.43008(19) 0.0371(10) Uani 1 1 d . . . . .
H20 H 0.687899 0.127600 0.453246 0.044 Uiso 1 1 calc R . . . .
C21 C 0.6787(3) 0.2534(8) 0.37298(19) 0.0363(10) Uani 1 1 d . . . . .
C22 C 0.6408(3) 0.4210(8) 0.33741(18) 0.0370(11) Uani 1 1 d . . . . .
H22 H 0.650665 0.424773 0.298596 0.044 Uiso 1 1 calc R . . . .
C23 C 0.7841(3) -0.1377(9) 0.39904(19) 0.0411(11) Uani 1 1 d . . . . .
H23A H 0.810533 -0.042719 0.429567 0.049 Uiso 1 1 calc R . . . .
H23B H 0.736436 -0.220763 0.414184 0.049 Uiso 1 1 calc R . . . .
C24 C 0.8438(3) -0.3193(9) 0.3782(2) 0.0494(13) Uani 1 1 d . . . . .
H24A H 0.817254 -0.412079 0.347350 0.059 Uiso 1 1 calc R . . . .
H24B H 0.891312 -0.235229 0.363213 0.059 Uiso 1 1 calc R . . . .
C25 C 0.8732(3) -0.4885(11) 0.4238(2) 0.0555(14) Uani 1 1 d . . . . .
H25A H 0.903520 -0.398992 0.453067 0.083 Uiso 1 1 calc GR . . . .
H25B H 0.908919 -0.609229 0.408120 0.083 Uiso 1 1 calc GR . . . .
H25C H 0.826136 -0.566981 0.439963 0.083 Uiso 1 1 calc GR . . . .
H2A H 0.533(3) 0.818(10) 0.3054(8) 0.067 Uiso 1 1 d DR . . . .
Fe1 Fe 0.11984(4) 0.86421(13) 0.36695(3) 0.0333(2) Uani 1 1 d . . . . .
N1 N 0.4553(2) 1.0736(6) 0.37929(14) 0.0302(8) Uani 1 1 d . . . . .
N2 N 0.5428(2) 0.7723(7) 0.33969(14) 0.0346(9) Uani 1 1 d D . . . .
N3 N 0.5193(2) 0.7620(7) 0.43134(14) 0.0309(8) Uani 1 1 d . . . . .
O1 O 0.38653(19) 1.3679(6) 0.33596(11) 0.0363(7) Uani 1 1 d . . . . .
O2 O 0.4563(2) 1.1097(6) 0.28353(11) 0.0408(8) Uani 1 1 d . . . . .
S1 S 0.75019(8) 0.0585(2) 0.34286(5) 0.0431(3) 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
C1 C2 1.423(6) . ?
C1 C5 1.417(6) . ?
C1 C11 1.459(6) . ?
C1 Fe1 2.064(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.429(6) . ?
C2 Fe1 2.064(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.418(7) . ?
C3 Fe1 2.045(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.417(6) . ?
C4 Fe1 2.041(5) . ?
C5 H5 0.9500 . ?
C5 Fe1 2.037(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.403(7) . ?
C6 C10 1.412(7) . ?
C6 Fe1 2.051(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.423(7) . ?
C7 Fe1 2.053(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.422(7) . ?
C8 Fe1 2.058(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.411(7) . ?
C9 Fe1 2.058(5) . ?
C10 H10 0.9500 . ?
C10 Fe1 2.047(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.323(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.503(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 N1 1.478(5) . ?
C14 N1 1.370(5) . ?
C14 O1 1.346(5) . ?
C14 O2 1.214(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 O1 1.433(5) . ?
C16 N1 1.385(6) . ?
C16 N2 1.368(5) . ?
C16 N3 1.315(5) . ?
C17 C18 1.404(6) . ?
C17 C22 1.385(6) . ?
C17 N2 1.391(6) . ?
C18 C19 1.393(6) . ?
C18 N3 1.387(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.404(6) . ?
C21 C22 1.396(6) . ?
C21 S1 1.776(5) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.511(7) . ?
C23 S1 1.807(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.510(7) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N2 H2A 0.869(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C11 127.4(4) . . ?
C2 C1 Fe1 69.8(3) . . ?
C5 C1 C2 107.4(4) . . ?
C5 C1 C11 125.2(4) . . ?
C5 C1 Fe1 68.7(3) . . ?
C11 C1 Fe1 125.4(3) . . ?
C1 C2 H2 126.0 . . ?
C1 C2 C3 108.0(4) . . ?
C1 C2 Fe1 69.8(2) . . ?
C3 C2 H2 126.0 . . ?
C3 C2 Fe1 69.0(3) . . ?
Fe1 C2 H2 126.8 . . ?
C2 C3 H3 126.0 . . ?
C2 C3 Fe1 70.3(2) . . ?
C4 C3 C2 108.0(4) . . ?
C4 C3 H3 126.0 . . ?
C4 C3 Fe1 69.5(3) . . ?
Fe1 C3 H3 125.7 . . ?
C3 C4 H4 126.2 . . ?
C3 C4 Fe1 69.9(3) . . ?
C5 C4 C3 107.7(4) . . ?
C5 C4 H4 126.2 . . ?
C5 C4 Fe1 69.5(3) . . ?
Fe1 C4 H4 126.0 . . ?
C1 C5 C4 109.0(4) . . ?
C1 C5 H5 125.5 . . ?
C1 C5 Fe1 70.8(3) . . ?
C4 C5 H5 125.5 . . ?
C4 C5 Fe1 69.8(3) . . ?
Fe1 C5 H5 125.4 . . ?
C7 C6 H6 126.0 . . ?
C7 C6 C10 108.0(5) . . ?
C7 C6 Fe1 70.1(3) . . ?
C10 C6 H6 126.0 . . ?
C10 C6 Fe1 69.7(3) . . ?
Fe1 C6 H6 125.8 . . ?
C6 C7 H7 126.0 . . ?
C6 C7 C8 108.0(5) . . ?
C6 C7 Fe1 69.9(3) . . ?
C8 C7 H7 126.0 . . ?
C8 C7 Fe1 69.9(3) . . ?
Fe1 C7 H7 125.7 . . ?
C7 C8 H8 126.0 . . ?
C7 C8 Fe1 69.6(3) . . ?
C9 C8 C7 108.0(5) . . ?
C9 C8 H8 126.0 . . ?
C9 C8 Fe1 69.8(3) . . ?
Fe1 C8 H8 126.2 . . ?
C8 C9 H9 126.4 . . ?
C8 C9 Fe1 69.8(3) . . ?
C10 C9 C8 107.1(5) . . ?
C10 C9 H9 126.4 . . ?
C10 C9 Fe1 69.5(3) . . ?
Fe1 C9 H9 125.9 . . ?
C6 C10 H10 125.6 . . ?
C6 C10 Fe1 70.0(3) . . ?
C9 C10 C6 108.9(5) . . ?
C9 C10 H10 125.6 . . ?
C9 C10 Fe1 70.3(3) . . ?
Fe1 C10 H10 125.7 . . ?
C1 C11 H11 117.2 . . ?
C12 C11 C1 125.7(4) . . ?
C12 C11 H11 117.2 . . ?
C11 C12 H12 117.2 . . ?
C11 C12 C13 125.7(4) . . ?
C13 C12 H12 117.2 . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
N1 C13 C12 112.9(3) . . ?
N1 C13 H13A 109.0 . . ?
N1 C13 H13B 109.0 . . ?
O1 C14 N1 110.4(3) . . ?
O2 C14 N1 126.0(4) . . ?
O2 C14 O1 123.6(4) . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
N2 C16 N1 124.1(4) . . ?
N3 C16 N1 122.4(4) . . ?
N3 C16 N2 113.5(4) . . ?
C22 C17 C18 122.6(4) . . ?
C22 C17 N2 132.6(4) . . ?
N2 C17 C18 104.7(4) . . ?
C19 C18 C17 119.5(4) . . ?
N3 C18 C17 110.5(4) . . ?
N3 C18 C19 130.0(4) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 C18 118.9(4) . . ?
C20 C19 H19 120.6 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.0(4) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 S1 122.1(4) . . ?
C22 C21 C20 121.1(4) . . ?
C22 C21 S1 116.8(3) . . ?
C17 C22 C21 116.9(4) . . ?
C17 C22 H22 121.5 . . ?
C21 C22 H22 121.5 . . ?
H23A C23 H23B 108.1 . . ?
C24 C23 H23A 109.6 . . ?
C24 C23 H23B 109.6 . . ?
C24 C23 S1 110.4(3) . . ?
S1 C23 H23A 109.6 . . ?
S1 C23 H23B 109.6 . . ?
C23 C24 H24A 109.2 . . ?
C23 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
C25 C24 C23 112.1(4) . . ?
C25 C24 H24A 109.2 . . ?
C25 C24 H24B 109.2 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C2 Fe1 C1 40.34(17) . . ?
C3 Fe1 C1 68.34(18) . . ?
C3 Fe1 C2 40.70(18) . . ?
C3 Fe1 C6 160.6(2) . . ?
C3 Fe1 C7 124.1(2) . . ?
C3 Fe1 C8 107.4(2) . . ?
C3 Fe1 C9 121.2(2) . . ?
C3 Fe1 C10 157.0(2) . . ?
C4 Fe1 C1 68.38(18) . . ?
C4 Fe1 C2 68.25(19) . . ?
C4 Fe1 C3 40.60(19) . . ?
C4 Fe1 C6 157.7(2) . . ?
C4 Fe1 C7 160.7(2) . . ?
C4 Fe1 C8 124.1(2) . . ?
C4 Fe1 C9 107.6(2) . . ?
C4 Fe1 C10 122.2(2) . . ?
C5 Fe1 C1 40.42(17) . . ?
C5 Fe1 C2 67.86(19) . . ?
C5 Fe1 C3 68.20(19) . . ?
C5 Fe1 C4 40.67(18) . . ?
C5 Fe1 C6 122.6(2) . . ?
C5 Fe1 C7 157.2(2) . . ?
C5 Fe1 C8 161.1(2) . . ?
C5 Fe1 C9 124.88(19) . . ?
C5 Fe1 C10 109.0(2) . . ?
C6 Fe1 C1 108.46(19) . . ?
C6 Fe1 C2 124.6(2) . . ?
C6 Fe1 C7 40.0(2) . . ?
C6 Fe1 C8 67.6(2) . . ?
C6 Fe1 C9 68.0(2) . . ?
C7 Fe1 C1 121.7(2) . . ?
C7 Fe1 C2 107.80(19) . . ?
C7 Fe1 C8 40.5(2) . . ?
C7 Fe1 C9 68.1(2) . . ?
C8 Fe1 C1 156.8(2) . . ?
C8 Fe1 C2 121.6(2) . . ?
C8 Fe1 C9 40.41(19) . . ?
C9 Fe1 C1 161.46(19) . . ?
C9 Fe1 C2 156.75(19) . . ?
C10 Fe1 C1 125.38(19) . . ?
C10 Fe1 C2 161.37(19) . . ?
C10 Fe1 C6 40.3(2) . . ?
C10 Fe1 C7 67.5(2) . . ?
C10 Fe1 C8 67.5(2) . . ?
C10 Fe1 C9 40.21(19) . . ?
C14 N1 C13 120.6(4) . . ?
C14 N1 C16 122.1(4) . . ?
C16 N1 C13 117.3(3) . . ?
C16 N2 C17 106.6(3) . . ?
C16 N2 H2A 122(4) . . ?
C17 N2 H2A 131(4) . . ?
C16 N3 C18 104.7(3) . . ?
C14 O1 C15 115.4(3) . . ?
C21 S1 C23 105.1(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2A O2 0.869(5) 2.11(5) 2.691(5) 123(5) . yes
N2 H2A O2 0.869(5) 2.44(4) 3.088(4) 132(5) 2_645 yes

_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.298
_oxdiff_exptl_absorpt_empirical_full_min 0.651
