# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_Rajnak_CRRM75B
_database_code_depnum_ccdc_archive 'CCDC 2154593'
loop_
_audit_author_name
_audit_author_address
'Erika Samolova'
;Czech Academy of Science, UC San Diego
Czech Republic
;
_audit_update_record             
;
2022-02-24 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2021-06-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C20 H21 Cl4 Fe N4 O3'
_chemical_formula_sum            'C20 H21 Cl4 Fe N4 O3'
_chemical_formula_weight         563.070
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Fe 0.35822 0.84933 11.76950 7.35730 3.52220 2.30450 4.76110 0.30720 15.35350
76.88050 1.03690004349
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   14.2923(8)
_cell_length_b                   10.0590(7)
_cell_length_c                   16.1597(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.143(2)
_cell_angle_gamma                90
_cell_volume                     2293.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      2.73
_exptl_absorpt_coefficient_mu    1.155
_exptl_absorpt_correction_T_max  0.6466
_exptl_absorpt_correction_T_min  0.5890
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0563 before and 0.0408 after correction.
The Ratio of minimum to maximum transmission is 0.9109.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_description       block
_exptl_crystal_F_000             1152.206
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9984
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            46929
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9984
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.72
_diffrn_reflns_theta_min         1.77
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9984
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -17
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -11
_reflns_number_gt                3635
_reflns_number_total             4382
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.4024
_refine_diff_density_min         -0.3621
_refine_diff_density_rms         0.0913
_refine_ls_d_res_high            0.8189
_refine_ls_d_res_low             11.5169
_refine_ls_goodness_of_fit_ref   1.0480
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4382
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.0480
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0257P)²+1.7383P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0601
_refine_ls_wR_factor_ref         0.0652
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), N2(H2), N3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C8(H8a,H8b), C9(H9a,H9b), C10(H10a,H10b), C11(H11a,H11b),
 C12(H12a,H12b), C13(H13a,H13b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3a), C5(H5), C17(H17), C19(H19)
;
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_refinement_flags_posn
Fe1 Fe 0.69936(2) 0.58386(3) 0.388821(18) 0.01319(8) Uani 1.000000 .
Cl1 Cl 1.13423(4) 0.59013(6) 0.20657(3) 0.02216(13) Uani 1.000000 .
Cl2 Cl 0.95605(4) 0.87937(5) 0.41613(3) 0.02219(13) Uani 1.000000 .
Cl3 Cl 0.42485(4) 0.60019(6) 0.21525(3) 0.02659(14) Uani 1.000000 .
Cl4 Cl 0.25822(4) 0.84946(6) 0.45040(4) 0.02669(14) Uani 1.000000 .
O1 O 0.79616(10) 0.70122(14) 0.35869(9) 0.0162(3) Uani 1.000000 .
O2 O 0.60207(10) 0.68634(14) 0.32083(9) 0.0167(3) Uani 1.000000 .
O3 O 0.44432(11) 0.37800(17) 0.38736(10) 0.0290(4) Uani 1.000000 .
N1 N 0.73533(12) 0.44106(17) 0.29813(10) 0.0150(4) Uani 1.000000 .
H1 H 0.67795(12) 0.40619(17) 0.27190(10) 0.0180(5) Uiso 1.000000 R
N2 N 0.80669(12) 0.46293(18) 0.47040(11) 0.0185(4) Uani 1.000000 .
H2 H 0.77235(12) 0.40527(18) 0.49910(11) 0.0222(5) Uiso 1.000000 R
N3 N 0.68317(12) 0.69702(17) 0.49882(10) 0.0142(4) Uani 1.000000 .
H3 H 0.64724(12) 0.64497(17) 0.52952(10) 0.0170(4) Uiso 1.000000 R
N4 N 0.60694(13) 0.44352(18) 0.41645(12) 0.0205(4) Uani 1.000000 .
C1 C 0.87039(14) 0.6776(2) 0.32167(12) 0.0138(4) Uani 1.000000 .
C2 C 0.95363(15) 0.7534(2) 0.34132(12) 0.0153(4) Uani 1.000000 .
C3 C 1.03414(15) 0.7314(2) 0.30532(13) 0.0173(5) Uani 1.000000 .
H3a H 1.08877(15) 0.7857(2) 0.31919(13) 0.0207(5) Uiso 1.000000 R
C4 C 1.03250(15) 0.6283(2) 0.24874(13) 0.0164(4) Uani 1.000000 .
C5 C 0.95198(15) 0.5522(2) 0.22584(13) 0.0162(4) Uani 1.000000 .
H5 H 0.95228(15) 0.4826(2) 0.18616(13) 0.0194(5) Uiso 1.000000 R
C6 C 0.87081(15) 0.5767(2) 0.26031(13) 0.0150(4) Uani 1.000000 .
C7 C 0.78146(15) 0.4981(2) 0.22997(13) 0.0164(4) Uani 1.000000 .
H7a H 0.79728(15) 0.4248(2) 0.19375(13) 0.0197(5) Uiso 1.000000 R
H7b H 0.73556(15) 0.5570(2) 0.19514(13) 0.0197(5) Uiso 1.000000 R
C8 C 0.78783(15) 0.3275(2) 0.34248(14) 0.0188(5) Uani 1.000000 .
H8a H 0.74242(15) 0.2650(2) 0.36187(14) 0.0226(6) Uiso 1.000000 R
H8b H 0.82259(15) 0.2793(2) 0.30342(14) 0.0226(6) Uiso 1.000000 R
C9 C 0.85706(15) 0.3766(2) 0.41683(14) 0.0197(5) Uani 1.000000 .
H9a H 0.90848(15) 0.4276(2) 0.39702(14) 0.0236(6) Uiso 1.000000 R
H9b H 0.88582(15) 0.2999(2) 0.44992(14) 0.0236(6) Uiso 1.000000 R
C10 C 0.87406(15) 0.5307(2) 0.53560(14) 0.0215(5) Uani 1.000000 .
H10a H 0.91552(15) 0.4637(2) 0.56789(14) 0.0258(6) Uiso 1.000000 R
H10b H 0.91470(15) 0.5911(2) 0.50845(14) 0.0258(6) Uiso 1.000000 R
C11 C 0.82384(16) 0.6097(2) 0.59479(14) 0.0224(5) Uani 1.000000 .
H11a H 0.77789(16) 0.5506(2) 0.61650(14) 0.0269(6) Uiso 1.000000 R
H11b H 0.87111(16) 0.6380(2) 0.64313(14) 0.0269(6) Uiso 1.000000 R
C12 C 0.77153(15) 0.7318(2) 0.55655(13) 0.0182(5) Uani 1.000000 .
H12a H 0.81372(15) 0.7830(2) 0.52534(13) 0.0219(6) Uiso 1.000000 R
H12b H 0.75540(15) 0.7893(2) 0.60200(13) 0.0219(6) Uiso 1.000000 R
C13 C 0.62703(14) 0.8199(2) 0.47513(13) 0.0148(4) Uani 1.000000 .
H13a H 0.62037(14) 0.8704(2) 0.52647(13) 0.0178(5) Uiso 1.000000 R
H13b H 0.66143(14) 0.8767(2) 0.43995(13) 0.0178(5) Uiso 1.000000 R
C14 C 0.52987(15) 0.7886(2) 0.42768(13) 0.0151(4) Uani 1.000000 .
C15 C 0.52388(15) 0.7198(2) 0.35062(13) 0.0152(4) Uani 1.000000 .
C16 C 0.43321(15) 0.6904(2) 0.30775(13) 0.0182(5) Uani 1.000000 .
C17 C 0.35183(15) 0.7293(2) 0.33736(14) 0.0202(5) Uani 1.000000 .
H17 H 0.29109(15) 0.7095(2) 0.30668(14) 0.0242(6) Uiso 1.000000 R
C18 C 0.36051(15) 0.7976(2) 0.41253(14) 0.0191(5) Uani 1.000000 .
C19 C 0.44857(15) 0.8263(2) 0.45827(13) 0.0166(5) Uani 1.000000 .
H19 H 0.45323(15) 0.8716(2) 0.51034(13) 0.0199(5) Uiso 1.000000 R
C20 C 0.52580(17) 0.4121(2) 0.40104(13) 0.0197(5) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O1 1.9388(14) . ?
Fe1 O2 1.9282(14) . ?
Fe1 N1 2.1714(17) . ?
Fe1 N2 2.2199(18) . ?
Fe1 N3 2.1539(17) . ?
Fe1 N4 2.0308(18) . ?
Cl1 C4 1.744(2) . ?
Cl2 C2 1.748(2) . ?
Cl3 C16 1.737(2) . ?
Cl4 C18 1.752(2) . ?
O1 C1 1.320(2) . ?
O2 C15 1.328(2) . ?
O3 C20 1.200(3) . ?
N1 H1 0.9300 . ?
N1 C7 1.486(3) . ?
N1 C8 1.487(3) . ?
N2 H2 0.9300 . ?
N2 C9 1.490(3) . ?
N2 C10 1.476(3) . ?
N3 H3 0.9300 . ?
N3 C12 1.488(3) . ?
N3 C13 1.491(3) . ?
N4 C20 1.190(3) . ?
C1 C2 1.406(3) . ?
C1 C6 1.419(3) . ?
C2 C3 1.387(3) . ?
C3 H3a 0.9500 . ?
C3 C4 1.380(3) . ?
C4 C5 1.382(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(3) . ?
C6 C7 1.516(3) . ?
C7 H7a 0.9900 . ?
C7 H7b 0.9900 . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C8 C9 1.513(3) . ?
C9 H9a 0.9900 . ?
C9 H9b 0.9900 . ?
C10 H10a 0.9900 . ?
C10 H10b 0.9900 . ?
C10 C11 1.510(3) . ?
C11 H11a 0.9900 . ?
C11 H11b 0.9900 . ?
C11 C12 1.518(3) . ?
C12 H12a 0.9900 . ?
C12 H12b 0.9900 . ?
C13 H13a 0.9900 . ?
C13 H13b 0.9900 . ?
C13 C14 1.509(3) . ?
C14 C15 1.415(3) . ?
C14 C19 1.386(3) . ?
C15 C16 1.400(3) . ?
C16 C17 1.383(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(3) . ?
C18 C19 1.385(3) . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Fe1 O1 90.58(6) . . ?
N1 Fe1 O1 88.76(6) . . ?
N1 Fe1 O2 101.29(6) . . ?
N2 Fe1 O1 91.69(6) . . ?
N2 Fe1 O2 177.50(6) . . ?
N2 Fe1 N1 79.80(6) . . ?
N3 Fe1 O1 93.44(6) . . ?
N3 Fe1 O2 91.45(6) . . ?
N3 Fe1 N1 167.05(6) . . ?
N3 Fe1 N2 87.38(6) . . ?
N4 Fe1 O1 173.46(7) . . ?
N4 Fe1 O2 93.53(7) . . ?
N4 Fe1 N1 85.44(7) . . ?
N4 Fe1 N2 84.30(7) . . ?
N4 Fe1 N3 91.55(7) . . ?
C1 O1 Fe1 131.40(13) . . ?
C15 O2 Fe1 120.06(12) . . ?
H1 N1 Fe1 105.72(5) . . ?
C7 N1 Fe1 115.17(12) . . ?
C7 N1 H1 105.72(10) . . ?
C8 N1 Fe1 109.77(12) . . ?
C8 N1 H1 105.72(11) . . ?
C8 N1 C7 113.87(16) . . ?
H2 N2 Fe1 105.56(5) . . ?
C9 N2 Fe1 109.05(13) . . ?
C9 N2 H2 105.56(11) . . ?
C10 N2 Fe1 118.78(13) . . ?
C10 N2 H2 105.56(11) . . ?
C10 N2 C9 111.30(17) . . ?
H3 N3 Fe1 106.48(5) . . ?
C12 N3 Fe1 116.75(12) . . ?
C12 N3 H3 106.48(10) . . ?
C13 N3 Fe1 110.52(12) . . ?
C13 N3 H3 106.48(10) . . ?
C13 N3 C12 109.54(16) . . ?
C20 N4 Fe1 141.73(17) . . ?
C2 C1 O1 120.81(18) . . ?
C6 C1 O1 122.58(18) . . ?
C6 C1 C2 116.62(18) . . ?
C1 C2 Cl2 118.19(16) . . ?
C3 C2 Cl2 118.63(16) . . ?
C3 C2 C1 123.17(19) . . ?
H3a C3 C2 120.99(12) . . ?
C4 C3 C2 118.02(19) . . ?
C4 C3 H3a 120.99(12) . . ?
C3 C4 Cl1 119.79(17) . . ?
C5 C4 Cl1 118.94(16) . . ?
C5 C4 C3 121.26(19) . . ?
H5 C5 C4 119.72(12) . . ?
C6 C5 C4 120.55(19) . . ?
C6 C5 H5 119.72(12) . . ?
C5 C6 C1 120.29(19) . . ?
C7 C6 C1 120.13(18) . . ?
C7 C6 C5 119.55(18) . . ?
C6 C7 N1 114.33(17) . . ?
H7a C7 N1 108.68(10) . . ?
H7a C7 C6 108.68(11) . . ?
H7b C7 N1 108.68(11) . . ?
H7b C7 C6 108.68(11) . . ?
H7b C7 H7a 107.6 . . ?
H8a C8 N1 109.57(11) . . ?
H8b C8 N1 109.57(11) . . ?
H8b C8 H8a 108.1 . . ?
C9 C8 N1 110.40(17) . . ?
C9 C8 H8a 109.57(12) . . ?
C9 C8 H8b 109.57(12) . . ?
C8 C9 N2 109.64(17) . . ?
H9a C9 N2 109.74(11) . . ?
H9a C9 C8 109.74(12) . . ?
H9b C9 N2 109.74(11) . . ?
H9b C9 C8 109.74(11) . . ?
H9b C9 H9a 108.2 . . ?
H10a C10 N2 109.23(11) . . ?
H10b C10 N2 109.23(11) . . ?
H10b C10 H10a 107.9 . . ?
C11 C10 N2 111.92(18) . . ?
C11 C10 H10a 109.23(12) . . ?
C11 C10 H10b 109.23(13) . . ?
H11a C11 C10 108.55(12) . . ?
H11b C11 C10 108.55(12) . . ?
H11b C11 H11a 107.5 . . ?
C12 C11 C10 114.89(18) . . ?
C12 C11 H11a 108.55(12) . . ?
C12 C11 H11b 108.55(11) . . ?
C11 C12 N3 112.27(17) . . ?
H12a C12 N3 109.15(10) . . ?
H12a C12 C11 109.15(12) . . ?
H12b C12 N3 109.15(10) . . ?
H12b C12 C11 109.15(12) . . ?
H12b C12 H12a 107.9 . . ?
H13a C13 N3 109.26(10) . . ?
H13b C13 N3 109.26(10) . . ?
H13b C13 H13a 107.9 . . ?
C14 C13 N3 111.79(16) . . ?
C14 C13 H13a 109.26(11) . . ?
C14 C13 H13b 109.26(11) . . ?
C15 C14 C13 118.13(18) . . ?
C19 C14 C13 121.15(19) . . ?
C19 C14 C15 120.71(19) . . ?
C14 C15 O2 120.39(18) . . ?
C16 C15 O2 122.20(19) . . ?
C16 C15 C14 117.41(19) . . ?
C15 C16 Cl3 117.89(17) . . ?
C17 C16 Cl3 119.94(16) . . ?
C17 C16 C15 122.2(2) . . ?
H17 C17 C16 120.62(13) . . ?
C18 C17 C16 118.8(2) . . ?
C18 C17 H17 120.62(13) . . ?
C17 C18 Cl4 119.42(17) . . ?
C19 C18 Cl4 119.31(17) . . ?
C19 C18 C17 121.3(2) . . ?
C18 C19 C14 119.7(2) . . ?
H19 C19 C14 120.17(12) . . ?
H19 C19 C18 120.17(13) . . ?
N4 C20 O3 178.2(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
N3 H3 O3 0.9300 2.032(2) 2.888(2) 152.24(7) 3_666

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O1 C1 C2 -148.04(17) . . . . ?
Fe1 O1 C1 C6 32.44(18) . . . . ?
Fe1 O2 C15 C14 54.75(15) . . . . ?
Fe1 O2 C15 C16 -125.87(15) . . . . ?
Fe1 N1 C7 C6 56.02(14) . . . . ?
Fe1 N1 C8 C9 -40.10(13) . . . . ?
Fe1 N2 C9 C8 -37.56(13) . . . . ?
Fe1 N2 C10 C11 56.83(15) . . . . ?
Fe1 N3 C12 C11 -63.17(14) . . . . ?
Fe1 N3 C13 C14 58.90(13) . . . . ?
Cl1 C4 C3 C2 -176.11(16) . . . . ?
Cl1 C4 C5 C6 177.75(16) . . . . ?
Cl2 C2 C1 O1 0.09(18) . . . . ?
Cl2 C2 C1 C6 179.64(15) . . . . ?
Cl2 C2 C3 C4 177.55(16) . . . . ?
Cl3 C16 C15 O2 3.16(19) . . . . ?
Cl3 C16 C15 C14 -177.44(15) . . . . ?
Cl3 C16 C17 C18 178.05(17) . . . . ?
Cl4 C18 C17 C16 179.21(17) . . . . ?
Cl4 C18 C19 C14 -178.37(16) . . . . ?
O1 C1 C2 C3 178.94(19) . . . . ?
O1 C1 C6 C5 -177.30(19) . . . . ?
O1 C1 C6 C7 4.7(2) . . . . ?
O2 C15 C14 C13 -1.1(2) . . . . ?
O2 C15 C14 C19 178.60(18) . . . . ?
O2 C15 C16 C17 -177.72(19) . . . . ?
N1 C7 C6 C1 -50.6(2) . . . . ?
N1 C7 C6 C5 131.40(18) . . . . ?
N1 C8 C9 N2 52.42(18) . . . . ?
N2 C10 C11 C12 -69.3(2) . . . . ?
N3 C12 C11 C10 73.46(19) . . . . ?
N3 C13 C14 C15 -60.78(19) . . . . ?
N3 C13 C14 C19 119.50(17) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
C1 C6 C5 C4 -2.0(2) . . . . ?
C2 C3 C4 C5 2.5(2) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C4 C5 C6 C7 175.95(19) . . . . ?
C13 C14 C15 C16 179.47(18) . . . . ?
C13 C14 C19 C18 179.07(19) . . . . ?
C14 C15 C16 C17 1.7(2) . . . . ?
C14 C19 C18 C17 1.3(2) . . . . ?
C15 C16 C17 C18 -1.0(2) . . . . ?
C16 C17 C18 C19 -0.5(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_crrm73
_database_code_depnum_ccdc_archive 'CCDC 2154595'
loop_
_audit_author_name
_audit_author_address
'Milan Gembicky'
;UC San Diego
United States of America
;
_audit_update_record             
;
2022-02-24 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2021-04-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 Cl4 Fe N4 O2 S'
_chemical_formula_sum            'C20 H21 Cl4 Fe N4 O2 S'
_chemical_formula_weight         579.12
_chemical_absolute_configuration .
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   7.4978(11)
_cell_length_b                   11.2446(15)
_cell_length_c                   27.190(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2292.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5179
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.82
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.772
_exptl_absorpt_coefficient_mu    1.242
_exptl_absorpt_correction_T_max  0.6464
_exptl_absorpt_correction_T_min  0.4939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1212 before and 0.0822 after correction.
The Ratio of minimum to maximum transmission is 0.7258.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1180
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0882
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            23408
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.688
_diffrn_reflns_theta_min         2.818
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3801
_reflns_number_total             4343
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.37(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0287P)²+1.0977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0841
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.63(3)
 0.37(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3.a Ternary CH refined with riding coordinates:
 N2(H2), N3(H3), N4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C14(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4A), C6(H6), C16(H16), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_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
Fe1 Fe 0.43064(10) 0.49438(6) 0.62681(2) 0.01812(18) Uani 1 1 d . . . . .
Cl1 Cl 0.89953(19) 0.59132(12) 0.72095(5) 0.0255(3) Uani 1 1 d . . . . .
Cl2 Cl 0.8840(2) 1.04020(12) 0.65144(5) 0.0328(4) Uani 1 1 d . . . . .
Cl3 Cl 0.1791(2) -0.09416(12) 0.56027(5) 0.0279(3) Uani 1 1 d . . . . .
Cl4 Cl 0.33433(19) 0.32213(11) 0.47342(5) 0.0228(3) Uani 1 1 d . . . . .
S1 S 0.3422(2) 0.84461(13) 0.71959(6) 0.0354(4) Uani 1 1 d . . . . .
O1 O 0.6752(5) 0.5387(3) 0.63393(13) 0.0221(8) Uani 1 1 d . . . . .
O2 O 0.4737(5) 0.3872(3) 0.57276(12) 0.0199(8) Uani 1 1 d . . . . .
N1 N 0.3637(6) 0.6106(4) 0.68568(16) 0.0232(10) Uani 1 1 d . . . . .
N2 N 0.3799(6) 0.6424(4) 0.57834(15) 0.0200(10) Uani 1 1 d . . . . .
H2 H 0.317444 0.704796 0.598077 0.024 Uiso 1 1 calc R U . . .
N3 N 0.1393(6) 0.4620(4) 0.62464(15) 0.0218(10) Uani 1 1 d . . . . .
H3 H 0.084245 0.526117 0.645116 0.026 Uiso 1 1 calc R U . . .
N4 N 0.4176(6) 0.3495(4) 0.67646(15) 0.0221(10) Uani 1 1 d . . . . .
H4 H 0.486422 0.373805 0.706317 0.026 Uiso 1 1 calc R U . . .
C1 C 0.3566(8) 0.7074(5) 0.70044(19) 0.0272(13) Uani 1 1 d . . . . .
C2 C 0.7233(7) 0.6529(5) 0.63843(19) 0.0200(12) Uani 1 1 d . . . . .
C3 C 0.8320(7) 0.6926(5) 0.67672(19) 0.0201(12) Uani 1 1 d . . . . .
C4 C 0.8844(8) 0.8111(5) 0.6803(2) 0.0248(13) Uani 1 1 d . . . . .
H4A H 0.961025 0.836059 0.706134 0.030 Uiso 1 1 calc R U . . .
C5 C 0.8242(8) 0.8915(5) 0.6461(2) 0.0251(12) Uani 1 1 d . . . . .
C6 C 0.7129(8) 0.8565(5) 0.6077(2) 0.0250(13) Uani 1 1 d . . . . .
H6 H 0.670399 0.913284 0.584657 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6646(8) 0.7368(5) 0.60343(19) 0.0219(12) Uani 1 1 d . . . . .
C8 C 0.5519(8) 0.6937(5) 0.56180(19) 0.0220(12) Uani 1 1 d . . . . .
H8A H 0.527722 0.760905 0.539236 0.026 Uiso 1 1 calc R U . . .
H8B H 0.618855 0.632622 0.543186 0.026 Uiso 1 1 calc R U . . .
C9 C 0.2639(7) 0.6138(5) 0.53577(19) 0.0219(12) Uani 1 1 d . . . . .
H9A H 0.314413 0.544784 0.517971 0.026 Uiso 1 1 calc R U . . .
H9B H 0.262778 0.682316 0.512897 0.026 Uiso 1 1 calc R U . . .
C10 C 0.0741(8) 0.5854(5) 0.55096(19) 0.0241(12) Uani 1 1 d . . . . .
H10A H 0.031724 0.649044 0.573243 0.029 Uiso 1 1 calc R U . . .
H10B H -0.002171 0.587202 0.521235 0.029 Uiso 1 1 calc R U . . .
C11 C 0.0479(8) 0.4673(5) 0.57627(18) 0.0212(12) Uani 1 1 d . . . . .
H11A H -0.081312 0.453296 0.581097 0.025 Uiso 1 1 calc R U . . .
H11B H 0.094420 0.403137 0.554901 0.025 Uiso 1 1 calc R U . . .
C12 C 0.0999(8) 0.3488(5) 0.65041(19) 0.0247(13) Uani 1 1 d . . . . .
H12A H 0.110171 0.281566 0.627094 0.030 Uiso 1 1 calc R U . . .
H12B H -0.023616 0.350427 0.663263 0.030 Uiso 1 1 calc R U . . .
C13 C 0.2306(8) 0.3319(5) 0.6927(2) 0.0268(13) Uani 1 1 d . . . . .
H13A H 0.202536 0.389375 0.719166 0.032 Uiso 1 1 calc R U . . .
H13B H 0.217041 0.250747 0.706268 0.032 Uiso 1 1 calc R U . . .
C14 C 0.5074(8) 0.2417(5) 0.65672(19) 0.0266(14) Uani 1 1 d . . . . .
H14A H 0.501206 0.177540 0.681607 0.032 Uiso 1 1 calc R U . . .
H14B H 0.634822 0.259923 0.650895 0.032 Uiso 1 1 calc R U . . .
C15 C 0.4249(8) 0.1977(4) 0.60928(18) 0.0197(11) Uani 1 1 d . . . . .
C16 C 0.3563(8) 0.0834(5) 0.60635(19) 0.0237(12) Uani 1 1 d . . . . .
H16 H 0.361987 0.031487 0.633873 0.028 Uiso 1 1 calc R U . . .
C17 C 0.2790(7) 0.0460(5) 0.5625(2) 0.0214(12) Uani 1 1 d . . . . .
C18 C 0.2727(7) 0.1171(5) 0.5218(2) 0.0221(12) Uani 1 1 d . . . . .
H18 H 0.221363 0.089306 0.491988 0.027 Uiso 1 1 calc R U . . .
C19 C 0.3434(7) 0.2311(4) 0.52506(18) 0.0176(11) Uani 1 1 d . . . . .
C20 C 0.4166(8) 0.2755(4) 0.56906(18) 0.0186(11) 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 O1 1.910(4) . ?
Fe1 O2 1.928(3) . ?
Fe1 N1 2.127(4) . ?
Fe1 N2 2.156(4) . ?
Fe1 N3 2.215(5) . ?
Fe1 N4 2.119(4) . ?
Cl1 C3 1.732(5) . ?
Cl2 C5 1.737(6) . ?
Cl3 C17 1.746(5) . ?
Cl4 C19 1.739(5) . ?
S1 C1 1.632(6) . ?
O1 C2 1.340(6) . ?
O2 C20 1.331(6) . ?
N1 C1 1.161(7) . ?
N2 H2 1.0000 . ?
N2 C8 1.483(7) . ?
N2 C9 1.483(6) . ?
N3 H3 1.0000 . ?
N3 C11 1.484(6) . ?
N3 C12 1.482(6) . ?
N4 H4 1.0000 . ?
N4 C13 1.483(7) . ?
N4 C14 1.487(7) . ?
C2 C3 1.396(7) . ?
C2 C7 1.410(7) . ?
C3 C4 1.392(7) . ?
C4 H4A 0.9500 . ?
C4 C5 1.372(8) . ?
C5 C6 1.394(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.398(7) . ?
C7 C8 1.493(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.516(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.509(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.523(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.513(7) . ?
C15 C16 1.387(7) . ?
C15 C20 1.401(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(7) . ?
C17 C18 1.367(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(7) . ?
C19 C20 1.407(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 O2 94.57(15) . . ?
O1 Fe1 N1 89.42(16) . . ?
O1 Fe1 N2 91.73(16) . . ?
O1 Fe1 N3 172.85(16) . . ?
O1 Fe1 N4 100.39(17) . . ?
O2 Fe1 N1 175.99(17) . . ?
O2 Fe1 N2 92.64(15) . . ?
O2 Fe1 N3 92.41(16) . . ?
O2 Fe1 N4 90.72(16) . . ?
N1 Fe1 N2 86.79(17) . . ?
N1 Fe1 N3 83.60(17) . . ?
N2 Fe1 N3 86.36(16) . . ?
N4 Fe1 N1 88.99(17) . . ?
N4 Fe1 N2 167.13(19) . . ?
N4 Fe1 N3 81.08(17) . . ?
C2 O1 Fe1 121.2(3) . . ?
C20 O2 Fe1 126.4(3) . . ?
C1 N1 Fe1 147.9(4) . . ?
Fe1 N2 H2 107.2 . . ?
C8 N2 Fe1 109.4(3) . . ?
C8 N2 H2 107.2 . . ?
C9 N2 Fe1 114.4(3) . . ?
C9 N2 H2 107.2 . . ?
C9 N2 C8 110.9(4) . . ?
Fe1 N3 H3 105.9 . . ?
C11 N3 Fe1 118.2(3) . . ?
C11 N3 H3 105.9 . . ?
C12 N3 Fe1 109.0(3) . . ?
C12 N3 H3 105.9 . . ?
C12 N3 C11 111.2(4) . . ?
Fe1 N4 H4 106.4 . . ?
C13 N4 Fe1 109.6(3) . . ?
C13 N4 H4 106.4 . . ?
C13 N4 C14 115.3(4) . . ?
C14 N4 Fe1 112.1(3) . . ?
C14 N4 H4 106.4 . . ?
N1 C1 S1 178.0(6) . . ?
O1 C2 C3 122.1(5) . . ?
O1 C2 C7 119.7(5) . . ?
C3 C2 C7 118.1(5) . . ?
C2 C3 Cl1 118.6(4) . . ?
C4 C3 Cl1 119.9(4) . . ?
C4 C3 C2 121.5(5) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 C3 119.4(5) . . ?
C5 C4 H4A 120.3 . . ?
C4 C5 Cl2 119.6(4) . . ?
C4 C5 C6 121.2(5) . . ?
C6 C5 Cl2 119.2(4) . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.3(5) . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C8 118.1(5) . . ?
C6 C7 C2 120.4(5) . . ?
C6 C7 C8 121.5(5) . . ?
N2 C8 C7 112.9(4) . . ?
N2 C8 H8A 109.0 . . ?
N2 C8 H8B 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N2 C9 H9A 109.1 . . ?
N2 C9 H9B 109.1 . . ?
N2 C9 C10 112.5(4) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C9 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 C9 115.6(5) . . ?
C11 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
N3 C11 C10 112.3(4) . . ?
N3 C11 H11A 109.1 . . ?
N3 C11 H11B 109.1 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
N3 C12 H12A 109.7 . . ?
N3 C12 H12B 109.7 . . ?
N3 C12 C13 109.6(5) . . ?
H12A C12 H12B 108.2 . . ?
C13 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
N4 C13 C12 111.6(4) . . ?
N4 C13 H13A 109.3 . . ?
N4 C13 H13B 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
N4 C14 H14A 109.0 . . ?
N4 C14 H14B 109.0 . . ?
N4 C14 C15 112.9(5) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C16 C15 C14 120.2(5) . . ?
C16 C15 C20 121.1(5) . . ?
C20 C15 C14 118.7(5) . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 119.0(5) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 Cl3 118.8(4) . . ?
C18 C17 Cl3 119.0(4) . . ?
C18 C17 C16 122.1(5) . . ?
C17 C18 H18 120.8 . . ?
C17 C18 C19 118.3(5) . . ?
C19 C18 H18 120.8 . . ?
C18 C19 Cl4 118.4(4) . . ?
C18 C19 C20 122.0(5) . . ?
C20 C19 Cl4 119.5(4) . . ?
O2 C20 C15 121.0(4) . . ?
O2 C20 C19 121.6(5) . . ?
C15 C20 C19 117.3(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O1 C2 C3 127.8(4) . . . . ?
Fe1 O1 C2 C7 -52.7(6) . . . . ?
Fe1 O2 C20 C15 -43.0(7) . . . . ?
Fe1 O2 C20 C19 136.0(4) . . . . ?
Fe1 N2 C8 C7 -59.4(5) . . . . ?
Fe1 N2 C9 C10 67.5(5) . . . . ?
Fe1 N3 C11 C10 -57.3(5) . . . . ?
Fe1 N3 C12 C13 33.4(5) . . . . ?
Fe1 N4 C13 C12 40.0(5) . . . . ?
Fe1 N4 C14 C15 -60.6(5) . . . . ?
Cl1 C3 C4 C5 -177.4(4) . . . . ?
Cl2 C5 C6 C7 -179.9(4) . . . . ?
Cl3 C17 C18 C19 176.2(4) . . . . ?
Cl4 C19 C20 O2 2.4(7) . . . . ?
Cl4 C19 C20 C15 -178.5(4) . . . . ?
O1 C2 C3 Cl1 -2.4(7) . . . . ?
O1 C2 C3 C4 178.5(5) . . . . ?
O1 C2 C7 C6 179.7(5) . . . . ?
O1 C2 C7 C8 -0.9(8) . . . . ?
N2 C9 C10 C11 -72.2(6) . . . . ?
N3 C12 C13 N4 -49.7(6) . . . . ?
N4 C14 C15 C16 -121.2(6) . . . . ?
N4 C14 C15 C20 57.6(7) . . . . ?
C2 C3 C4 C5 1.7(8) . . . . ?
C2 C7 C8 N2 62.4(7) . . . . ?
C3 C2 C7 C6 -0.8(8) . . . . ?
C3 C2 C7 C8 178.6(5) . . . . ?
C3 C4 C5 Cl2 178.2(4) . . . . ?
C3 C4 C5 C6 -0.6(9) . . . . ?
C4 C5 C6 C7 -1.2(9) . . . . ?
C5 C6 C7 C2 1.9(8) . . . . ?
C5 C6 C7 C8 -177.5(5) . . . . ?
C6 C7 C8 N2 -118.3(6) . . . . ?
C7 C2 C3 Cl1 178.1(4) . . . . ?
C7 C2 C3 C4 -1.0(8) . . . . ?
C8 N2 C9 C10 -168.1(4) . . . . ?
C9 N2 C8 C7 173.4(4) . . . . ?
C9 C10 C11 N3 65.4(6) . . . . ?
C11 N3 C12 C13 165.4(4) . . . . ?
C12 N3 C11 C10 175.6(4) . . . . ?
C13 N4 C14 C15 65.7(6) . . . . ?
C14 N4 C13 C12 -87.5(5) . . . . ?
C14 C15 C16 C17 179.1(5) . . . . ?
C14 C15 C20 O2 -2.5(8) . . . . ?
C14 C15 C20 C19 178.4(5) . . . . ?
C15 C16 C17 Cl3 -175.6(4) . . . . ?
C15 C16 C17 C18 1.8(9) . . . . ?
C16 C15 C20 O2 176.3(5) . . . . ?
C16 C15 C20 C19 -2.8(8) . . . . ?
C16 C17 C18 C19 -1.2(8) . . . . ?
C17 C18 C19 Cl4 -179.6(4) . . . . ?
C17 C18 C19 C20 -1.5(8) . . . . ?
C18 C19 C20 O2 -175.7(5) . . . . ?
C18 C19 C20 C15 3.4(8) . . . . ?
C20 C15 C16 C17 0.3(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.63(3)
2 0.37(3)

####################################################################### 
# 
# 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_crrm71
_database_code_depnum_ccdc_archive 'CCDC 2154600'
loop_
_audit_author_name
_audit_author_address
'Milan Gembicky'
;UC San Diego
United States of America
;
_audit_update_record             
;
2022-02-24 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2021-03-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 Cl5 Fe N3 O2'
_chemical_formula_sum            'C19 H21 Cl5 Fe N3 O2'
_chemical_formula_weight         556.49
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.9994(16)
_cell_length_b                   8.9714(14)
_cell_length_c                   22.698(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.368(4)
_cell_angle_gamma                90
_cell_volume                     2221.4(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9257
_cell_measurement_temperature    90.0
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.829
_exptl_absorpt_coefficient_mu    1.303
_exptl_absorpt_correction_T_max  0.4910
_exptl_absorpt_correction_T_min  0.3957
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1023 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.8059.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            27413
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.430
_diffrn_reflns_theta_min         1.809
_diffrn_ambient_temperature      90.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3656
_reflns_number_total             4552
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4552
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+5.1287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1050
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), N2(H2), N3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5), C15(H15), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.43590(4) 0.56004(5) 0.63280(2) 0.01546(13) Uani 1 1 d . . . . .
Cl1 Cl 0.53260(8) 0.36593(9) 0.58401(4) 0.02198(19) Uani 1 1 d . . . . .
Cl2 Cl 0.09966(8) 0.65042(10) 0.88704(4) 0.0247(2) Uani 1 1 d . . . . .
Cl3 Cl 0.14401(8) 0.90537(9) 0.67674(4) 0.0237(2) Uani 1 1 d . . . . .
Cl4 Cl 0.85640(8) 0.63457(10) 0.69011(4) 0.0272(2) Uani 1 1 d . . . . .
Cl5 Cl 0.88945(9) 0.87014(11) 0.47381(4) 0.0297(2) Uani 1 1 d . . . . .
O1 O 0.5892(2) 0.6649(3) 0.65302(10) 0.0182(5) Uani 1 1 d . . . . .
O2 O 0.3520(2) 0.7010(3) 0.67624(10) 0.0187(5) Uani 1 1 d . . . . .
N1 N 0.3922(3) 0.6790(3) 0.55049(12) 0.0173(6) Uani 1 1 d . . . . .
H1 H 0.415865 0.613401 0.518201 0.021 Uiso 1 1 calc R U . . .
N2 N 0.2609(3) 0.4352(3) 0.60913(13) 0.0214(6) Uani 1 1 d . . . . .
H2 H 0.277893 0.357220 0.579774 0.026 Uiso 1 1 calc R U . . .
N3 N 0.4446(3) 0.4090(3) 0.70701(12) 0.0183(6) Uani 1 1 d . . . . .
H3 H 0.525222 0.356645 0.708657 0.022 Uiso 1 1 calc R U . . .
C1 C 0.6585(3) 0.7117(3) 0.61324(15) 0.0175(7) Uani 1 1 d . . . . .
C2 C 0.7866(3) 0.7029(4) 0.62274(15) 0.0197(7) Uani 1 1 d . . . . .
C3 C 0.8582(3) 0.7521(4) 0.58116(16) 0.0218(8) Uani 1 1 d . . . . .
H3A H 0.944972 0.745302 0.588616 0.026 Uiso 1 1 calc R U . . .
C4 C 0.8020(3) 0.8112(4) 0.52853(16) 0.0210(7) Uani 1 1 d . . . . .
C5 C 0.6768(3) 0.8275(4) 0.51803(16) 0.0212(8) Uani 1 1 d . . . . .
H5 H 0.639873 0.870057 0.481761 0.025 Uiso 1 1 calc R U . . .
C6 C 0.6044(3) 0.7818(4) 0.56027(15) 0.0179(7) Uani 1 1 d . . . . .
C7 C 0.4703(3) 0.8137(4) 0.55212(15) 0.0180(7) Uani 1 1 d . . . . .
H7A H 0.451291 0.878675 0.584999 0.022 Uiso 1 1 calc R U . . .
H7B H 0.449394 0.869558 0.514570 0.022 Uiso 1 1 calc R U . . .
C8 C 0.2631(3) 0.7242(4) 0.53293(16) 0.0201(7) Uani 1 1 d . . . . .
H8A H 0.257474 0.781105 0.495320 0.024 Uiso 1 1 calc R U . . .
H8B H 0.237550 0.791063 0.563780 0.024 Uiso 1 1 calc R U . . .
C9 C 0.1754(3) 0.5929(4) 0.52462(16) 0.0251(8) Uani 1 1 d . . . . .
H9A H 0.096044 0.627965 0.503706 0.030 Uiso 1 1 calc R U . . .
H9B H 0.208778 0.518258 0.498868 0.030 Uiso 1 1 calc R U . . .
C10 C 0.1527(3) 0.5179(4) 0.58181(17) 0.0270(8) Uani 1 1 d . . . . .
H10A H 0.130478 0.594235 0.610051 0.032 Uiso 1 1 calc R U . . .
H10B H 0.082661 0.448321 0.573596 0.032 Uiso 1 1 calc R U . . .
C11 C 0.2324(3) 0.3542(4) 0.66285(16) 0.0239(8) Uani 1 1 d . . . . .
H11A H 0.174000 0.272344 0.651069 0.029 Uiso 1 1 calc R U . . .
H11B H 0.193908 0.423200 0.689038 0.029 Uiso 1 1 calc R U . . .
C12 C 0.3495(3) 0.2914(4) 0.69580(15) 0.0211(7) Uani 1 1 d . . . . .
H12A H 0.332436 0.248673 0.734106 0.025 Uiso 1 1 calc R U . . .
H12B H 0.380221 0.210307 0.672066 0.025 Uiso 1 1 calc R U . . .
C13 C 0.4467(3) 0.4873(4) 0.76517(15) 0.0191(7) Uani 1 1 d . . . . .
H13A H 0.520792 0.550775 0.771693 0.023 Uiso 1 1 calc R U . . .
H13B H 0.453015 0.411988 0.797299 0.023 Uiso 1 1 calc R U . . .
C14 C 0.3353(3) 0.5831(4) 0.76947(15) 0.0169(7) Uani 1 1 d . . . . .
C15 C 0.2745(3) 0.5728(4) 0.81900(15) 0.0188(7) Uani 1 1 d . . . . .
H15 H 0.301604 0.503691 0.849612 0.023 Uiso 1 1 calc R U . . .
C16 C 0.1746(3) 0.6625(4) 0.82401(15) 0.0193(7) Uani 1 1 d . . . . .
C17 C 0.1325(3) 0.7641(4) 0.78086(15) 0.0199(7) Uani 1 1 d . . . . .
H17 H 0.062906 0.824380 0.784618 0.024 Uiso 1 1 calc R U . . .
C18 C 0.1948(3) 0.7758(4) 0.73160(15) 0.0176(7) Uani 1 1 d . . . . .
C19 C 0.2962(3) 0.6873(4) 0.72396(15) 0.0177(7) 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 Cl1 2.3859(9) . ?
Fe1 O1 1.934(2) . ?
Fe1 O2 1.912(2) . ?
Fe1 N1 2.152(3) . ?
Fe1 N2 2.232(3) . ?
Fe1 N3 2.154(3) . ?
Cl2 C16 1.744(3) . ?
Cl3 C18 1.743(3) . ?
Cl4 C2 1.733(4) . ?
Cl5 C4 1.747(3) . ?
O1 C1 1.323(4) . ?
O2 C19 1.318(4) . ?
N1 H1 1.0000 . ?
N1 C7 1.481(4) . ?
N1 C8 1.482(4) . ?
N2 H2 1.0000 . ?
N2 C10 1.471(5) . ?
N2 C11 1.487(5) . ?
N3 H3 1.0000 . ?
N3 C12 1.484(4) . ?
N3 C13 1.493(4) . ?
C1 C2 1.401(5) . ?
C1 C6 1.418(5) . ?
C2 C3 1.376(5) . ?
C3 H3A 0.9500 . ?
C3 C4 1.379(5) . ?
C4 C5 1.376(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(5) . ?
C6 C7 1.490(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.518(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.511(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.513(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.510(5) . ?
C14 C15 1.383(5) . ?
C14 C19 1.418(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.379(5) . ?
C16 C17 1.374(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(5) . ?
C18 C19 1.398(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
O1 Fe1 Cl1 92.18(7) . . ?
O1 Fe1 N1 93.19(10) . . ?
O1 Fe1 N2 178.93(10) . . ?
O1 Fe1 N3 99.81(10) . . ?
O2 Fe1 Cl1 174.51(7) . . ?
O2 Fe1 O1 91.12(10) . . ?
O2 Fe1 N1 92.92(10) . . ?
O2 Fe1 N2 89.88(11) . . ?
O2 Fe1 N3 89.36(10) . . ?
N1 Fe1 Cl1 91.28(8) . . ?
N1 Fe1 N2 87.16(11) . . ?
N1 Fe1 N3 166.75(11) . . ?
N2 Fe1 Cl1 86.79(8) . . ?
N3 Fe1 Cl1 85.76(8) . . ?
N3 Fe1 N2 79.80(11) . . ?
C1 O1 Fe1 123.6(2) . . ?
C19 O2 Fe1 132.0(2) . . ?
Fe1 N1 H1 107.1 . . ?
C7 N1 Fe1 108.6(2) . . ?
C7 N1 H1 107.1 . . ?
C7 N1 C8 108.5(3) . . ?
C8 N1 Fe1 118.0(2) . . ?
C8 N1 H1 107.1 . . ?
Fe1 N2 H2 106.4 . . ?
C10 N2 Fe1 118.3(2) . . ?
C10 N2 H2 106.4 . . ?
C10 N2 C11 110.4(3) . . ?
C11 N2 Fe1 108.3(2) . . ?
C11 N2 H2 106.4 . . ?
Fe1 N3 H3 106.0 . . ?
C12 N3 Fe1 110.7(2) . . ?
C12 N3 H3 106.0 . . ?
C12 N3 C13 114.6(3) . . ?
C13 N3 Fe1 112.9(2) . . ?
C13 N3 H3 106.0 . . ?
O1 C1 C2 122.3(3) . . ?
O1 C1 C6 120.3(3) . . ?
C2 C1 C6 117.4(3) . . ?
C1 C2 Cl4 118.6(3) . . ?
C3 C2 Cl4 119.4(3) . . ?
C3 C2 C1 121.9(3) . . ?
C2 C3 H3A 120.5 . . ?
C2 C3 C4 119.1(3) . . ?
C4 C3 H3A 120.5 . . ?
C3 C4 Cl5 120.4(3) . . ?
C5 C4 Cl5 118.4(3) . . ?
C5 C4 C3 121.2(3) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 119.4(3) . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 C7 120.3(3) . . ?
N1 C7 C6 114.1(3) . . ?
N1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
N1 C8 C9 113.2(3) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 C8 114.3(3) . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
N2 C10 C9 111.9(3) . . ?
N2 C10 H10A 109.2 . . ?
N2 C10 H10B 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 H11A 109.8 . . ?
N2 C11 H11B 109.8 . . ?
N2 C11 C12 109.4(3) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
N3 C12 C11 110.9(3) . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N3 C13 H13A 108.8 . . ?
N3 C13 H13B 108.8 . . ?
N3 C13 C14 113.9(3) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 C19 120.2(3) . . ?
C19 C14 C13 120.1(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 Cl2 119.8(3) . . ?
C17 C16 Cl2 118.3(3) . . ?
C17 C16 C15 121.9(3) . . ?
C16 C17 H17 121.0 . . ?
C16 C17 C18 117.9(3) . . ?
C18 C17 H17 121.0 . . ?
C17 C18 Cl3 118.7(3) . . ?
C17 C18 C19 122.8(3) . . ?
C19 C18 Cl3 118.6(3) . . ?
O2 C19 C14 122.0(3) . . ?
O2 C19 C18 120.8(3) . . ?
C18 C19 C14 117.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O1 C1 C2 -140.5(3) . . . . ?
Fe1 O1 C1 C6 43.4(4) . . . . ?
Fe1 O2 C19 C14 31.7(5) . . . . ?
Fe1 O2 C19 C18 -148.1(3) . . . . ?
Fe1 N1 C7 C6 59.4(3) . . . . ?
Fe1 N1 C8 C9 -61.0(3) . . . . ?
Fe1 N2 C10 C9 58.5(4) . . . . ?
Fe1 N2 C11 C12 -39.7(3) . . . . ?
Fe1 N3 C12 C11 -37.2(3) . . . . ?
Fe1 N3 C13 C14 60.1(3) . . . . ?
Cl2 C16 C17 C18 178.3(3) . . . . ?
Cl3 C18 C19 O2 -0.3(4) . . . . ?
Cl3 C18 C19 C14 179.9(2) . . . . ?
Cl4 C2 C3 C4 -177.7(3) . . . . ?
Cl5 C4 C5 C6 179.9(3) . . . . ?
O1 C1 C2 Cl4 -2.4(4) . . . . ?
O1 C1 C2 C3 -179.9(3) . . . . ?
O1 C1 C6 C5 -178.4(3) . . . . ?
O1 C1 C6 C7 5.1(5) . . . . ?
N1 C8 C9 C10 72.2(4) . . . . ?
N2 C11 C12 N3 52.0(4) . . . . ?
N3 C13 C14 C15 132.1(3) . . . . ?
N3 C13 C14 C19 -50.3(4) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C1 C6 C7 N1 -62.9(4) . . . . ?
C2 C1 C6 C5 5.3(5) . . . . ?
C2 C1 C6 C7 -171.2(3) . . . . ?
C2 C3 C4 Cl5 -178.3(3) . . . . ?
C2 C3 C4 C5 2.7(5) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 C1 -3.0(5) . . . . ?
C4 C5 C6 C7 173.4(3) . . . . ?
C5 C6 C7 N1 120.6(3) . . . . ?
C6 C1 C2 Cl4 173.8(2) . . . . ?
C6 C1 C2 C3 -3.7(5) . . . . ?
C7 N1 C8 C9 175.1(3) . . . . ?
C8 N1 C7 C6 -171.3(3) . . . . ?
C8 C9 C10 N2 -70.6(4) . . . . ?
C10 N2 C11 C12 -170.7(3) . . . . ?
C11 N2 C10 C9 -176.0(3) . . . . ?
C12 N3 C13 C14 -67.9(4) . . . . ?
C13 N3 C12 C11 91.9(3) . . . . ?
C13 C14 C15 C16 178.4(3) . . . . ?
C13 C14 C19 O2 2.1(5) . . . . ?
C13 C14 C19 C18 -178.1(3) . . . . ?
C14 C15 C16 Cl2 -179.2(3) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C15 C14 C19 O2 179.7(3) . . . . ?
C15 C14 C19 C18 -0.5(5) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C16 C17 C18 Cl3 -179.3(3) . . . . ?
C16 C17 C18 C19 1.1(5) . . . . ?
C17 C18 C19 O2 179.3(3) . . . . ?
C17 C18 C19 C14 -0.5(5) . . . . ?
C19 C14 C15 C16 0.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_crmm74
_database_code_depnum_ccdc_archive 'CCDC 2154594'
loop_
_audit_author_name
_audit_author_address
'Milan Gembicky'
;UC San Diego
United States of America
;
_audit_update_record             
;
2022-02-24 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2021-04-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 Cl4 Fe N6 O2'
_chemical_formula_sum            'C19 H21 Cl4 Fe N6 O2'
_chemical_formula_weight         563.07
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.316(2)
_cell_length_b                   9.9354(17)
_cell_length_c                   16.168(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.476(6)
_cell_angle_gamma                90
_cell_volume                     2274.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2372
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.122
_cell_measurement_theta_min      2.412
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    1.164
_exptl_absorpt_correction_T_max  0.6462
_exptl_absorpt_correction_T_min  0.5600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1139 before and 0.0698 after correction.
The Ratio of minimum to maximum transmission is 0.8646.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             1148
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1185
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34740
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.362
_diffrn_reflns_theta_min         2.413
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2882
_reflns_number_total             4147
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.0033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4147
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²+0.8744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1175
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 N1-H1 = N2-H2 = N3-H3
 0.98 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C13(H13A,H13B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5), C15(H15), C17(H17)
;
_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
Fe1 Fe 0.29839(4) 0.57018(6) 0.61022(3) 0.02469(18) Uani 1 1 d . . . . .
Cl1 Cl 0.57474(8) 0.60425(11) 0.78882(6) 0.0377(3) Uani 1 1 d . . . . .
Cl2 Cl 0.73939(7) 0.86141(11) 0.55373(7) 0.0373(3) Uani 1 1 d . . . . .
Cl3 Cl 0.04932(7) 0.88056(10) 0.58395(6) 0.0322(3) Uani 1 1 d . . . . .
Cl4 Cl -0.13714(7) 0.59853(11) 0.79346(6) 0.0329(3) Uani 1 1 d . . . . .
O1 O 0.39836(18) 0.6656(3) 0.67781(16) 0.0285(6) Uani 1 1 d . . . . .
O2 O 0.20437(18) 0.6938(3) 0.64097(16) 0.0260(6) Uani 1 1 d . . . . .
N1 N 0.3166(2) 0.6846(3) 0.50119(19) 0.0249(7) Uani 1 1 d D . . . .
H1 H 0.355(2) 0.630(3) 0.470(2) 0.030 Uiso 1 1 d D U . . .
N2 N 0.1897(2) 0.4508(3) 0.5295(2) 0.0283(8) Uani 1 1 d D . . . .
H2 H 0.230(2) 0.392(3) 0.502(2) 0.034 Uiso 1 1 d D U . . .
N3 N 0.2590(2) 0.4287(3) 0.7011(2) 0.0268(8) Uani 1 1 d D . . . .
H3 H 0.3194(18) 0.396(4) 0.730(2) 0.032 Uiso 1 1 d D U . . .
N4 N 0.3840(2) 0.4202(3) 0.5786(2) 0.0332(8) Uani 1 1 d . . . . .
N5 N 0.4681(2) 0.4088(3) 0.5970(2) 0.0286(8) Uani 1 1 d . . . . .
N6 N 0.5491(3) 0.3935(4) 0.6132(2) 0.0389(9) Uani 1 1 d . . . . .
C1 C 0.4756(3) 0.7092(4) 0.6486(2) 0.0249(9) Uani 1 1 d . . . . .
C2 C 0.5661(3) 0.6902(4) 0.6946(2) 0.0294(9) Uani 1 1 d . . . . .
C3 C 0.6467(3) 0.7366(4) 0.6661(3) 0.0323(10) Uani 1 1 d . . . . .
H3A H 0.707173 0.723141 0.698185 0.039 Uiso 1 1 calc R U . . .
C4 C 0.6377(3) 0.8027(4) 0.5903(3) 0.0308(10) Uani 1 1 d . . . . .
C5 C 0.5500(3) 0.8231(4) 0.5436(2) 0.0281(9) Uani 1 1 d . . . . .
H5 H 0.545199 0.867673 0.491146 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4692(3) 0.7794(4) 0.5725(2) 0.0255(9) Uani 1 1 d . . . . .
C7 C 0.3730(3) 0.8093(4) 0.5253(2) 0.0269(9) Uani 1 1 d . . . . .
H7A H 0.338042 0.866671 0.560381 0.032 Uiso 1 1 calc R U . . .
H7B H 0.380160 0.860653 0.474127 0.032 Uiso 1 1 calc R U . . .
C8 C 0.2297(3) 0.7215(4) 0.4436(2) 0.0274(9) Uani 1 1 d . . . . .
H8A H 0.247119 0.778886 0.398209 0.033 Uiso 1 1 calc R U . . .
H8B H 0.187836 0.774715 0.474694 0.033 Uiso 1 1 calc R U . . .
C9 C 0.1761(3) 0.5991(4) 0.4054(3) 0.0351(10) Uani 1 1 d . . . . .
H9A H 0.129961 0.628785 0.357155 0.042 Uiso 1 1 calc R U . . .
H9B H 0.221337 0.537561 0.383894 0.042 Uiso 1 1 calc R U . . .
C10 C 0.1241(3) 0.5218(4) 0.4652(3) 0.0326(10) Uani 1 1 d . . . . .
H10A H 0.084928 0.584995 0.492719 0.039 Uiso 1 1 calc R U . . .
H10B H 0.081290 0.455573 0.433310 0.039 Uiso 1 1 calc R U . . .
C11 C 0.1375(3) 0.3664(4) 0.5834(2) 0.0313(10) Uani 1 1 d . . . . .
H11A H 0.107060 0.289836 0.550636 0.038 Uiso 1 1 calc R U . . .
H11B H 0.087451 0.420536 0.603767 0.038 Uiso 1 1 calc R U . . .
C12 C 0.2054(3) 0.3144(4) 0.6567(3) 0.0308(9) Uani 1 1 d . . . . .
H12A H 0.170044 0.266098 0.695782 0.037 Uiso 1 1 calc R U . . .
H12B H 0.250013 0.250185 0.636686 0.037 Uiso 1 1 calc R U . . .
C13 C 0.2125(3) 0.4877(4) 0.7690(2) 0.0267(9) Uani 1 1 d . . . . .
H13A H 0.258768 0.544825 0.804627 0.032 Uiso 1 1 calc R U . . .
H13B H 0.193964 0.413815 0.804353 0.032 Uiso 1 1 calc R U . . .
C14 C 0.1256(3) 0.5718(4) 0.7383(2) 0.0241(9) Uani 1 1 d . . . . .
C15 C 0.0437(3) 0.5502(4) 0.7737(2) 0.0286(9) Uani 1 1 d . . . . .
H15 H 0.041770 0.480233 0.813416 0.034 Uiso 1 1 calc R U . . .
C16 C -0.0348(3) 0.6311(4) 0.7508(2) 0.0260(9) Uani 1 1 d . . . . .
C17 C -0.0328(3) 0.7357(4) 0.6945(2) 0.0269(9) Uani 1 1 d . . . . .
H17 H -0.085741 0.793358 0.681087 0.032 Uiso 1 1 calc R U . . .
C18 C 0.0473(3) 0.7543(4) 0.6586(2) 0.0246(9) Uani 1 1 d . . . . .
C19 C 0.1288(3) 0.6727(4) 0.6779(2) 0.0253(9) 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 O1 1.918(3) . ?
Fe1 O2 1.940(3) . ?
Fe1 N1 2.145(3) . ?
Fe1 N2 2.221(3) . ?
Fe1 N3 2.167(3) . ?
Fe1 N4 2.041(3) . ?
Cl1 C2 1.735(4) . ?
Cl2 C4 1.750(4) . ?
Cl3 C18 1.744(4) . ?
Cl4 C16 1.739(4) . ?
O1 C1 1.337(4) . ?
O2 C19 1.327(4) . ?
N1 H1 0.958(19) . ?
N1 C7 1.499(5) . ?
N1 C8 1.486(5) . ?
N2 H2 0.979(19) . ?
N2 C10 1.474(5) . ?
N2 C11 1.489(5) . ?
N3 H3 0.974(19) . ?
N3 C12 1.494(5) . ?
N3 C13 1.487(5) . ?
N4 N5 1.203(5) . ?
N5 N6 1.160(5) . ?
C1 C2 1.408(5) . ?
C1 C6 1.407(5) . ?
C2 C3 1.383(6) . ?
C3 H3A 0.9500 . ?
C3 C4 1.381(6) . ?
C4 C5 1.382(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(5) . ?
C6 C7 1.502(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.519(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.514(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.509(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.520(5) . ?
C14 C15 1.394(5) . ?
C14 C19 1.405(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(5) . ?
C16 C17 1.384(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.372(5) . ?
C18 C19 1.417(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
O1 Fe1 O2 91.64(11) . . ?
O1 Fe1 N1 92.03(12) . . ?
O1 Fe1 N2 176.28(12) . . ?
O1 Fe1 N3 100.42(12) . . ?
O1 Fe1 N4 94.50(13) . . ?
O2 Fe1 N1 92.76(12) . . ?
O2 Fe1 N2 92.08(12) . . ?
O2 Fe1 N3 88.70(12) . . ?
O2 Fe1 N4 172.24(13) . . ?
N1 Fe1 N2 87.67(12) . . ?
N1 Fe1 N3 167.42(12) . . ?
N3 Fe1 N2 79.79(12) . . ?
N4 Fe1 N1 91.76(13) . . ?
N4 Fe1 N2 81.80(13) . . ?
N4 Fe1 N3 85.54(14) . . ?
C1 O1 Fe1 123.1(2) . . ?
C19 O2 Fe1 131.1(2) . . ?
Fe1 N1 H1 106(2) . . ?
C7 N1 Fe1 110.5(2) . . ?
C7 N1 H1 106(2) . . ?
C8 N1 Fe1 117.0(2) . . ?
C8 N1 H1 107(2) . . ?
C8 N1 C7 109.2(3) . . ?
Fe1 N2 H2 100(2) . . ?
C10 N2 Fe1 118.5(3) . . ?
C10 N2 H2 109(2) . . ?
C10 N2 C11 111.1(3) . . ?
C11 N2 Fe1 109.0(2) . . ?
C11 N2 H2 108(2) . . ?
Fe1 N3 H3 104(2) . . ?
C12 N3 Fe1 109.5(2) . . ?
C12 N3 H3 109(2) . . ?
C13 N3 Fe1 115.8(2) . . ?
C13 N3 H3 104(2) . . ?
C13 N3 C12 113.6(3) . . ?
N5 N4 Fe1 128.6(3) . . ?
N6 N5 N4 177.6(4) . . ?
O1 C1 C2 121.0(4) . . ?
O1 C1 C6 121.3(3) . . ?
C6 C1 C2 117.7(4) . . ?
C1 C2 Cl1 118.0(3) . . ?
C3 C2 Cl1 120.1(3) . . ?
C3 C2 C1 121.9(4) . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 C2 118.7(4) . . ?
C4 C3 H3A 120.6 . . ?
C3 C4 Cl2 119.0(3) . . ?
C3 C4 C5 120.9(4) . . ?
C5 C4 Cl2 120.1(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 118.7(3) . . ?
C5 C6 C1 120.2(4) . . ?
C5 C6 C7 121.1(4) . . ?
N1 C7 C6 112.7(3) . . ?
N1 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
N1 C8 C9 112.5(3) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 C8 114.4(3) . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
N2 C10 C9 111.7(3) . . ?
N2 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 H11A 109.8 . . ?
N2 C11 H11B 109.8 . . ?
N2 C11 C12 109.4(3) . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
N3 C12 C11 110.1(3) . . ?
N3 C12 H12A 109.6 . . ?
N3 C12 H12B 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.2 . . ?
N3 C13 H13A 108.7 . . ?
N3 C13 H13B 108.7 . . ?
N3 C13 C14 114.2(3) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C15 C14 C13 118.5(3) . . ?
C15 C14 C19 120.7(4) . . ?
C19 C14 C13 120.7(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.9(4) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 Cl4 118.9(3) . . ?
C17 C16 Cl4 120.1(3) . . ?
C17 C16 C15 121.0(4) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.6(4) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 Cl3 119.3(3) . . ?
C17 C18 C19 122.8(4) . . ?
C19 C18 Cl3 117.8(3) . . ?
O2 C19 C14 122.5(4) . . ?
O2 C19 C18 120.7(3) . . ?
C14 C19 C18 116.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O1 C1 C2 -134.7(3) . . . . ?
Fe1 O1 C1 C6 47.5(5) . . . . ?
Fe1 O2 C19 C14 33.1(5) . . . . ?
Fe1 O2 C19 C18 -148.1(3) . . . . ?
Fe1 N1 C7 C6 59.1(4) . . . . ?
Fe1 N1 C8 C9 -62.6(4) . . . . ?
Fe1 N2 C10 C9 57.3(4) . . . . ?
Fe1 N2 C11 C12 -38.2(4) . . . . ?
Fe1 N3 C12 C11 -41.1(4) . . . . ?
Fe1 N3 C13 C14 54.7(4) . . . . ?
Cl1 C2 C3 C4 178.9(3) . . . . ?
Cl2 C4 C5 C6 -178.8(3) . . . . ?
Cl3 C18 C19 O2 1.0(5) . . . . ?
Cl3 C18 C19 C14 179.9(3) . . . . ?
Cl4 C16 C17 C18 -176.5(3) . . . . ?
O1 C1 C2 Cl1 1.9(5) . . . . ?
O1 C1 C2 C3 -178.9(4) . . . . ?
O1 C1 C6 C5 -179.9(4) . . . . ?
O1 C1 C6 C7 2.2(6) . . . . ?
N1 C8 C9 C10 73.6(5) . . . . ?
N2 C11 C12 N3 53.5(4) . . . . ?
N3 C13 C14 C15 132.6(4) . . . . ?
N3 C13 C14 C19 -49.9(5) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C1 C6 C7 N1 -60.0(5) . . . . ?
C2 C1 C6 C5 2.2(6) . . . . ?
C2 C1 C6 C7 -175.7(4) . . . . ?
C2 C3 C4 Cl2 -179.9(3) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 0.9(6) . . . . ?
C4 C5 C6 C1 -2.2(6) . . . . ?
C4 C5 C6 C7 175.7(4) . . . . ?
C5 C6 C7 N1 122.0(4) . . . . ?
C6 C1 C2 Cl1 179.8(3) . . . . ?
C6 C1 C2 C3 -1.0(6) . . . . ?
C7 N1 C8 C9 171.1(3) . . . . ?
C8 N1 C7 C6 -171.0(3) . . . . ?
C8 C9 C10 N2 -70.1(5) . . . . ?
C10 N2 C11 C12 -170.6(3) . . . . ?
C11 N2 C10 C9 -175.3(3) . . . . ?
C12 N3 C13 C14 -73.2(4) . . . . ?
C13 N3 C12 C11 90.0(4) . . . . ?
C13 C14 C15 C16 175.9(4) . . . . ?
C13 C14 C19 O2 4.5(6) . . . . ?
C13 C14 C19 C18 -174.3(3) . . . . ?
C14 C15 C16 Cl4 178.0(3) . . . . ?
C14 C15 C16 C17 -1.5(6) . . . . ?
C15 C14 C19 O2 -178.0(3) . . . . ?
C15 C14 C19 C18 3.1(5) . . . . ?
C15 C16 C17 C18 2.9(6) . . . . ?
C16 C17 C18 Cl3 177.1(3) . . . . ?
C16 C17 C18 C19 -1.3(6) . . . . ?
C17 C18 C19 O2 179.5(4) . . . . ?
C17 C18 C19 C14 -1.7(6) . . . . ?
C19 C14 C15 C16 -1.6(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_crrm72
_database_code_depnum_ccdc_archive 'CCDC 2154596'
loop_
_audit_author_name
_audit_author_address
'Milan Gembicky'
;UC San Diego
United States of America
;
_audit_update_record             
;
2022-02-24 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2022-02-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 Cl4 Fe N4 O2 Se'
_chemical_formula_sum            'C20 H21 Cl4 Fe N4 O2 Se'
_chemical_formula_weight         626.02
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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                   7.4706(7)
_cell_length_b                   11.3083(11)
_cell_length_c                   27.472(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2320.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3874
_cell_measurement_temperature    90.0
_cell_measurement_theta_max      23.329
_cell_measurement_theta_min      2.333
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.774
_exptl_absorpt_coefficient_mu    2.706
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1133 before and 0.0798 after correction.
The Ratio of minimum to maximum transmission is 0.7876.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.012
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1008
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            23220
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.046
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_min         1.482
_diffrn_ambient_temperature      90.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II TXS - Artemis'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3058
_reflns_number_total             4098
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details 
;
 Flack x determined using 1051 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4098
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.000
_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)+(0.0443P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0992
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2), N3(H3), N4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4A), C6(H6), C16(H16), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_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
Se1 Se 0.30976(13) 0.15395(9) 0.27043(4) 0.0299(3) Uani 1 1 d . . . . .
Fe1 Fe 0.38937(14) 0.50578(11) 0.37473(4) 0.0159(3) Uani 1 1 d . . . . .
Cl1 Cl 0.8617(3) 0.4051(2) 0.28211(8) 0.0239(5) Uani 1 1 d . . . . .
Cl2 Cl 0.8391(3) -0.0417(2) 0.35070(9) 0.0301(6) Uani 1 1 d . . . . .
Cl3 Cl 0.2931(3) 0.67888(19) 0.52604(8) 0.0203(5) Uani 1 1 d . . . . .
Cl4 Cl 0.1385(3) 1.09313(19) 0.43979(8) 0.0254(6) Uani 1 1 d . . . . .
O1 O 0.6347(7) 0.4593(5) 0.3674(2) 0.0192(14) Uani 1 1 d . . . . .
O2 O 0.4333(7) 0.6137(5) 0.4275(2) 0.0161(14) Uani 1 1 d . . . . .
N1 N 0.3239(10) 0.3896(6) 0.3165(3) 0.0201(17) Uani 1 1 d . . . . .
N2 N 0.3361(8) 0.3568(6) 0.4228(2) 0.0182(17) Uani 1 1 d . . . . .
H2 H 0.271610 0.295475 0.403315 0.022 Uiso 1 1 calc R U . . .
N3 N 0.0980(8) 0.5361(6) 0.3770(2) 0.0155(16) Uani 1 1 d . . . . .
H3 H 0.042964 0.471594 0.357073 0.019 Uiso 1 1 calc R U . . .
N4 N 0.3746(9) 0.6496(6) 0.3249(3) 0.0206(17) Uani 1 1 d . . . . .
H4 H 0.443842 0.625343 0.295401 0.025 Uiso 1 1 calc R U . . .
C1 C 0.3196(11) 0.2982(9) 0.2979(3) 0.023(2) Uani 1 1 d . . . . .
C2 C 0.6800(10) 0.3450(8) 0.3637(3) 0.0171(19) Uani 1 1 d . . . . .
C3 C 0.7923(11) 0.3047(7) 0.3258(3) 0.016(2) Uani 1 1 d . . . . .
C4 C 0.8427(10) 0.1881(8) 0.3220(3) 0.022(2) Uani 1 1 d . . . . .
H4A H 0.919458 0.163554 0.296352 0.027 Uiso 1 1 calc R U . . .
C5 C 0.7807(12) 0.1061(8) 0.3559(3) 0.023(2) Uani 1 1 d . . . . .
C6 C 0.6685(11) 0.1426(8) 0.3931(3) 0.021(2) Uani 1 1 d . . . . .
H6 H 0.622816 0.085999 0.415413 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6219(11) 0.2606(8) 0.3982(3) 0.020(2) Uani 1 1 d . . . . .
C8 C 0.5078(11) 0.3043(8) 0.4391(3) 0.021(2) Uani 1 1 d . . . . .
H8A H 0.482042 0.237654 0.461346 0.025 Uiso 1 1 calc R U . . .
H8B H 0.575633 0.364493 0.457662 0.025 Uiso 1 1 calc R U . . .
C9 C 0.2221(10) 0.3865(8) 0.4652(3) 0.017(2) Uani 1 1 d . . . . .
H9A H 0.273787 0.455445 0.482366 0.020 Uiso 1 1 calc R U . . .
H9B H 0.221299 0.318909 0.488099 0.020 Uiso 1 1 calc R U . . .
C10 C 0.0284(11) 0.4152(8) 0.4501(3) 0.020(2) Uani 1 1 d . . . . .
H10A H -0.014932 0.351982 0.428122 0.024 Uiso 1 1 calc R U . . .
H10B H -0.047965 0.414311 0.479524 0.024 Uiso 1 1 calc R U . . .
C11 C 0.0052(11) 0.5336(8) 0.4247(3) 0.020(2) Uani 1 1 d . . . . .
H11A H -0.123993 0.548983 0.419675 0.024 Uiso 1 1 calc R U . . .
H11B H 0.053494 0.597137 0.445657 0.024 Uiso 1 1 calc R U . . .
C12 C 0.0579(10) 0.6487(8) 0.3508(3) 0.021(2) Uani 1 1 d . . . . .
H12A H 0.067786 0.716045 0.373710 0.026 Uiso 1 1 calc R U . . .
H12B H -0.066083 0.646579 0.338169 0.026 Uiso 1 1 calc R U . . .
C13 C 0.1875(11) 0.6657(8) 0.3091(3) 0.021(2) Uani 1 1 d . . . . .
H13A H 0.159707 0.608160 0.283031 0.025 Uiso 1 1 calc R U . . .
H13B H 0.172701 0.746211 0.295542 0.025 Uiso 1 1 calc R U . . .
C14 C 0.4614(12) 0.7574(7) 0.3439(3) 0.020(2) Uani 1 1 d . . . . .
H14A H 0.451355 0.820794 0.319162 0.024 Uiso 1 1 calc R U . . .
H14B H 0.590342 0.741151 0.348870 0.024 Uiso 1 1 calc R U . . .
C15 C 0.3834(11) 0.8008(7) 0.3906(3) 0.018(2) Uani 1 1 d . . . . .
C16 C 0.3135(11) 0.9158(8) 0.3940(3) 0.020(2) Uani 1 1 d . . . . .
H16 H 0.317944 0.967428 0.366752 0.024 Uiso 1 1 calc R U . . .
C17 C 0.2386(11) 0.9534(7) 0.4371(3) 0.020(2) Uani 1 1 d . . . . .
C18 C 0.2323(11) 0.8820(7) 0.4775(3) 0.018(2) Uani 1 1 d . . . . .
H18 H 0.180371 0.909387 0.506986 0.022 Uiso 1 1 calc R U . . .
C19 C 0.3039(11) 0.7685(7) 0.4743(3) 0.0165(19) Uani 1 1 d . . . . .
C20 C 0.3764(11) 0.7248(7) 0.4309(3) 0.016(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
Se1 C1 1.799(11) . ?
Fe1 O1 1.917(5) . ?
Fe1 O2 1.922(6) . ?
Fe1 N1 2.128(8) . ?
Fe1 N2 2.177(7) . ?
Fe1 N3 2.205(6) . ?
Fe1 N4 2.128(7) . ?
Cl1 C3 1.731(8) . ?
Cl2 C5 1.733(9) . ?
Cl3 C19 1.747(9) . ?
Cl4 C17 1.750(9) . ?
O1 C2 1.340(10) . ?
O2 C20 1.330(9) . ?
N1 C1 1.153(11) . ?
N2 H2 1.0000 . ?
N2 C8 1.483(10) . ?
N2 C9 1.481(10) . ?
N3 H3 1.0000 . ?
N3 C11 1.482(10) . ?
N3 C12 1.492(10) . ?
N4 H4 1.0000 . ?
N4 C13 1.475(11) . ?
N4 C14 1.477(10) . ?
C2 C3 1.411(11) . ?
C2 C7 1.414(12) . ?
C3 C4 1.375(11) . ?
C4 H4A 0.9500 . ?
C4 C5 1.393(12) . ?
C5 C6 1.384(12) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(12) . ?
C7 C8 1.494(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.540(11) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.519(12) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.512(11) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.492(12) . ?
C15 C16 1.404(12) . ?
C15 C20 1.403(12) . ?
C16 H16 0.9500 . ?
C16 C17 1.376(12) . ?
C17 C18 1.374(12) . ?
C18 H18 0.9500 . ?
C18 C19 1.393(11) . ?
C19 C20 1.400(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 O2 95.2(2) . . ?
O1 Fe1 N1 88.4(3) . . ?
O1 Fe1 N2 91.5(2) . . ?
O1 Fe1 N3 171.7(2) . . ?
O1 Fe1 N4 101.0(2) . . ?
O2 Fe1 N1 176.5(3) . . ?
O2 Fe1 N2 93.7(3) . . ?
O2 Fe1 N3 92.8(3) . . ?
O2 Fe1 N4 90.5(3) . . ?
N1 Fe1 N2 86.4(3) . . ?
N1 Fe1 N3 83.7(3) . . ?
N2 Fe1 N3 85.6(2) . . ?
N4 Fe1 N1 88.6(3) . . ?
N4 Fe1 N2 166.4(3) . . ?
N4 Fe1 N3 81.3(2) . . ?
C2 O1 Fe1 120.9(5) . . ?
C20 O2 Fe1 126.8(5) . . ?
C1 N1 Fe1 153.2(7) . . ?
Fe1 N2 H2 107.5 . . ?
C8 N2 Fe1 109.6(5) . . ?
C8 N2 H2 107.5 . . ?
C9 N2 Fe1 114.0(5) . . ?
C9 N2 H2 107.5 . . ?
C9 N2 C8 110.5(6) . . ?
Fe1 N3 H3 106.1 . . ?
C11 N3 Fe1 118.9(5) . . ?
C11 N3 H3 106.1 . . ?
C11 N3 C12 110.4(6) . . ?
C12 N3 Fe1 108.5(4) . . ?
C12 N3 H3 106.1 . . ?
Fe1 N4 H4 106.6 . . ?
C13 N4 Fe1 109.4(5) . . ?
C13 N4 H4 106.6 . . ?
C13 N4 C14 114.7(7) . . ?
C14 N4 Fe1 112.4(5) . . ?
C14 N4 H4 106.6 . . ?
N1 C1 Se1 178.4(8) . . ?
O1 C2 C3 121.2(8) . . ?
O1 C2 C7 121.5(7) . . ?
C3 C2 C7 117.3(8) . . ?
C2 C3 Cl1 118.5(6) . . ?
C4 C3 Cl1 119.6(7) . . ?
C4 C3 C2 121.9(8) . . ?
C3 C4 H4A 120.1 . . ?
C3 C4 C5 119.7(8) . . ?
C5 C4 H4A 120.1 . . ?
C4 C5 Cl2 120.2(7) . . ?
C6 C5 Cl2 120.0(7) . . ?
C6 C5 C4 119.8(8) . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 120.9(8) . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C8 117.1(8) . . ?
C6 C7 C2 120.3(8) . . ?
C6 C7 C8 122.6(8) . . ?
N2 C8 C7 113.5(7) . . ?
N2 C8 H8A 108.9 . . ?
N2 C8 H8B 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
N2 C9 H9A 109.2 . . ?
N2 C9 H9B 109.2 . . ?
N2 C9 C10 112.1(7) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C9 114.7(7) . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
N3 C11 C10 111.7(7) . . ?
N3 C11 H11A 109.3 . . ?
N3 C11 H11B 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
N3 C12 H12A 109.6 . . ?
N3 C12 H12B 109.6 . . ?
N3 C12 C13 110.2(7) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
N4 C13 C12 111.6(7) . . ?
N4 C13 H13A 109.3 . . ?
N4 C13 H13B 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
N4 C14 H14A 108.8 . . ?
N4 C14 H14B 108.8 . . ?
N4 C14 C15 113.8(7) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C16 C15 C14 120.5(8) . . ?
C20 C15 C14 119.4(8) . . ?
C20 C15 C16 120.1(8) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.6(8) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 Cl4 119.3(7) . . ?
C18 C17 Cl4 118.8(7) . . ?
C18 C17 C16 121.9(8) . . ?
C17 C18 H18 120.8 . . ?
C17 C18 C19 118.5(8) . . ?
C19 C18 H18 120.8 . . ?
C18 C19 Cl3 117.7(7) . . ?
C18 C19 C20 121.8(8) . . ?
C20 C19 Cl3 120.4(6) . . ?
O2 C20 C15 120.8(8) . . ?
O2 C20 C19 121.1(8) . . ?
C19 C20 C15 118.1(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O1 C2 C3 129.6(7) . . . . ?
Fe1 O1 C2 C7 -52.3(9) . . . . ?
Fe1 O2 C20 C15 -42.7(10) . . . . ?
Fe1 O2 C20 C19 135.7(7) . . . . ?
Fe1 N2 C8 C7 -59.6(8) . . . . ?
Fe1 N2 C9 C10 68.6(8) . . . . ?
Fe1 N3 C11 C10 -59.3(8) . . . . ?
Fe1 N3 C12 C13 33.4(8) . . . . ?
Fe1 N4 C13 C12 39.8(9) . . . . ?
Fe1 N4 C14 C15 -59.0(8) . . . . ?
Cl1 C3 C4 C5 -177.2(6) . . . . ?
Cl2 C5 C6 C7 179.3(7) . . . . ?
Cl3 C19 C20 O2 2.1(11) . . . . ?
Cl3 C19 C20 C15 -179.4(6) . . . . ?
Cl4 C17 C18 C19 176.6(6) . . . . ?
O1 C2 C3 Cl1 -3.3(10) . . . . ?
O1 C2 C3 C4 178.8(7) . . . . ?
O1 C2 C7 C6 179.0(7) . . . . ?
O1 C2 C7 C8 -0.1(11) . . . . ?
N2 C9 C10 C11 -72.5(10) . . . . ?
N3 C12 C13 N4 -49.8(10) . . . . ?
N4 C14 C15 C16 -122.2(9) . . . . ?
N4 C14 C15 C20 56.2(11) . . . . ?
C2 C3 C4 C5 0.7(12) . . . . ?
C2 C7 C8 N2 61.5(10) . . . . ?
C3 C2 C7 C6 -2.8(12) . . . . ?
C3 C2 C7 C8 178.1(7) . . . . ?
C3 C4 C5 Cl2 178.5(6) . . . . ?
C3 C4 C5 C6 0.2(12) . . . . ?
C4 C5 C6 C7 -2.4(13) . . . . ?
C5 C6 C7 C2 3.7(13) . . . . ?
C5 C6 C7 C8 -177.2(8) . . . . ?
C6 C7 C8 N2 -117.5(9) . . . . ?
C7 C2 C3 Cl1 178.5(6) . . . . ?
C7 C2 C3 C4 0.6(11) . . . . ?
C8 N2 C9 C10 -167.4(7) . . . . ?
C9 N2 C8 C7 174.0(7) . . . . ?
C9 C10 C11 N3 65.4(10) . . . . ?
C11 N3 C12 C13 165.4(7) . . . . ?
C12 N3 C11 C10 174.5(7) . . . . ?
C13 N4 C14 C15 66.9(9) . . . . ?
C14 N4 C13 C12 -87.6(9) . . . . ?
C14 C15 C16 C17 178.6(8) . . . . ?
C14 C15 C20 O2 -2.1(12) . . . . ?
C14 C15 C20 C19 179.4(8) . . . . ?
C15 C16 C17 Cl4 -175.7(6) . . . . ?
C15 C16 C17 C18 1.0(13) . . . . ?
C16 C15 C20 O2 176.4(7) . . . . ?
C16 C15 C20 C19 -2.1(12) . . . . ?
C16 C17 C18 C19 -0.1(12) . . . . ?
C17 C18 C19 Cl3 -179.6(6) . . . . ?
C17 C18 C19 C20 -1.9(12) . . . . ?
C18 C19 C20 O2 -175.4(7) . . . . ?
C18 C19 C20 C15 3.0(12) . . . . ?
C20 C15 C16 C17 0.1(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
