# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_pre6_a
_database_code_depnum_ccdc_archive 'CCDC 1999286'
loop_
_audit_author_name
_audit_author_address
'Jin Kim'
;Sunchon National University
South Korea
;
_audit_update_record             
;
2020-04-26 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_pre6_a              
;
PROBLEM: D-H Without Acceptor       O6       --H6B      .     Please Check
RESPONSE: This alert is related to the water moiety in which the hydrogen atoms have too low scattering power. Therefore these two hydrogens could not be freely refined from the difference density map.
;
# Added during the CSD deposition process: Sunday 26 April 2020 12:21 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H23 Fe N3 O3, 2(Cl O4), H2 O'
_chemical_formula_sum            'C16 H25 Cl2 Fe N3 O12'
_chemical_formula_weight         578.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   14.194(4)
_cell_length_b                   10.712(3)
_cell_length_c                   15.769(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.510(4)
_cell_angle_gamma                90
_cell_volume                     2340.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    15526
_cell_measurement_theta_min      1.470
_cell_measurement_theta_max      25.097

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   0.601
_exptl_transmission_factor_max   0.745
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.939
_shelx_estimated_absorpt_T_min   0.705
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15526
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.470
_diffrn_reflns_theta_max         25.097
_diffrn_reflns_theta_full        25.097
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             7959
_reflns_number_gt                6552
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.991

_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.51(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         7959
_refine_ls_number_parameters     639
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0864
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.75721(6) 0.70834(8) 0.08912(5) 0.0153(2) Uani 1 1 d . . . . .
Fe2 Fe 0.26219(6) 0.28339(7) 0.41619(5) 0.0140(2) Uani 1 1 d . . . . .
N1 N 0.8150(3) 0.8561(5) 0.1889(3) 0.0174(12) Uani 1 1 d . . . . .
N2 N 0.7191(4) 0.8771(5) 0.0180(3) 0.0182(12) Uani 1 1 d . . . . .
N3 N 0.8434(3) 0.6044(5) 0.1913(3) 0.0183(12) Uani 1 1 d . . . . .
N4 N 0.2027(3) 0.1367(5) 0.3166(3) 0.0155(12) Uani 1 1 d . . . . .
N5 N 0.1846(4) 0.3895(5) 0.3103(3) 0.0188(12) Uani 1 1 d . . . . .
N6 N 0.2834(3) 0.1164(5) 0.4901(3) 0.0191(13) Uani 1 1 d . . . . .
O1 O 0.6541(3) 0.5829(5) 0.0240(3) 0.0239(12) Uani 1 1 d . . . . .
O2 O 0.6427(3) 0.7203(4) 0.1596(3) 0.0192(10) Uani 1 1 d . . . . .
O3 O 0.8508(4) 0.6752(5) 0.0031(3) 0.0303(13) Uani 1 1 d . . . . .
O4 O 0.3834(3) 0.2548(4) 0.3559(3) 0.0197(10) Uani 1 1 d . . . . .
O5 O 0.3685(3) 0.3971(4) 0.4868(3) 0.0204(10) Uani 1 1 d . . . . .
O6 O 0.1667(3) 0.3345(4) 0.4991(3) 0.0221(11) Uani 1 1 d . . . . .
H6A H 0.168402 0.413510 0.505845 0.033 Uiso 1 1 d R U . . .
H6B H 0.188527 0.305654 0.549990 0.033 Uiso 1 1 d R U . . .
O7 O 0.8597(3) 0.0945(5) 0.4800(3) 0.0338(12) Uani 1 1 d . . . . .
O8 O 0.8838(4) 0.1162(6) 0.3381(3) 0.0523(18) Uani 1 1 d . . . . .
O9 O 0.9852(4) 0.2181(5) 0.4535(3) 0.0429(14) Uani 1 1 d . . . . .
O10 O 0.9905(4) -0.0014(5) 0.4414(3) 0.0387(14) Uani 1 1 d . . . . .
O11 O 0.5162(3) 0.3555(4) 0.6657(3) 0.0280(11) Uani 1 1 d . . . . .
O12 O 0.6356(3) 0.2462(5) 0.6130(3) 0.0388(13) Uani 1 1 d . . . . .
O13 O 0.5545(4) 0.1486(5) 0.7097(3) 0.0329(13) Uani 1 1 d . . . . .
O14 O 0.6648(3) 0.3089(4) 0.7588(3) 0.0315(11) Uani 1 1 d . . . . .
O15 O 0.4550(4) 0.8197(5) 0.7815(3) 0.0359(13) Uani 1 1 d . . . . .
O16 O 0.4401(4) 0.7125(5) 0.9069(3) 0.0425(13) Uani 1 1 d . . . . .
O17 O 0.4268(3) 0.6030(4) 0.7763(3) 0.0286(11) Uani 1 1 d . . . . .
O18 O 0.3042(3) 0.7403(5) 0.7934(3) 0.0482(14) Uani 1 1 d . . . . .
O19 O 0.1116(4) 0.8801(5) 0.1648(3) 0.0369(14) Uani 1 1 d . . . . .
O20 O 0.0149(4) 0.9834(5) 0.0471(3) 0.0437(15) Uani 1 1 d . . . . .
O21 O 0.0432(4) 0.7678(5) 0.0387(3) 0.0453(15) Uani 1 1 d . . . . .
O22 O 0.1675(4) 0.9113(5) 0.0380(4) 0.0508(16) Uani 1 1 d . . . . .
O23 O 0.5944(3) 0.4718(5) 0.8748(3) 0.0331(12) Uani 1 1 d G . . . .
O24 O 0.3460(3) 0.5709(4) 0.5966(3) 0.0317(12) Uani 1 1 d G . . . .
Cl1 Cl 0.93049(11) 0.10655(16) 0.42737(10) 0.0224(4) Uani 1 1 d . . . . .
Cl2 Cl 0.59236(10) 0.26396(14) 0.68594(10) 0.0180(4) Uani 1 1 d . . . . .
Cl3 Cl 0.40593(10) 0.72083(15) 0.81513(9) 0.0187(4) Uani 1 1 d . . . . .
Cl4 Cl 0.08445(11) 0.88516(16) 0.07230(11) 0.0254(4) Uani 1 1 d . . . . .
C1 C 0.6668(4) 0.8811(7) -0.0637(4) 0.0216(15) Uani 1 1 d . . . . .
H1A H 0.635797 0.806766 -0.088136 0.026 Uiso 1 1 calc R U . . .
C2 C 0.6558(5) 0.9860(7) -0.1135(5) 0.0276(17) Uani 1 1 d . . . . .
H2 H 0.618551 0.984987 -0.171380 0.033 Uiso 1 1 calc R U . . .
C3 C 0.7008(5) 1.0950(7) -0.0771(5) 0.0313(18) Uani 1 1 d . . . . .
H3 H 0.695267 1.169959 -0.109987 0.038 Uiso 1 1 calc R U . . .
C4 C 0.7531(5) 1.0928(7) 0.0068(5) 0.0277(17) Uani 1 1 d . . . . .
H4 H 0.782924 1.166811 0.032930 0.033 Uiso 1 1 calc R U . . .
C5 C 0.7622(5) 0.9817(6) 0.0535(4) 0.0191(15) Uani 1 1 d . . . . .
C6 C 0.8245(5) 0.9755(7) 0.1446(4) 0.0240(17) Uani 1 1 d . . . . .
H6C H 0.892844 0.987518 0.141566 0.029 Uiso 1 1 calc R U . . .
H6D H 0.806321 1.044778 0.179422 0.029 Uiso 1 1 calc R U . . .
C7 C 0.9077(4) 0.8076(6) 0.2393(4) 0.0204(15) Uani 1 1 d . . . . .
H7A H 0.925082 0.851809 0.295621 0.024 Uiso 1 1 calc R U . . .
H7B H 0.959171 0.823279 0.207089 0.024 Uiso 1 1 calc R U . . .
C8 C 0.9005(4) 0.6693(6) 0.2550(4) 0.0196(15) Uani 1 1 d . . . . .
C9 C 0.9510(4) 0.6124(7) 0.3305(4) 0.0255(16) Uani 1 1 d . . . . .
H9 H 0.990443 0.660057 0.375260 0.031 Uiso 1 1 calc R U . . .
C10 C 0.9423(5) 0.4838(7) 0.3387(5) 0.0318(18) Uani 1 1 d . . . . .
H10 H 0.976753 0.442653 0.389387 0.038 Uiso 1 1 calc R U . . .
C11 C 0.8842(4) 0.4165(7) 0.2741(4) 0.0273(17) Uani 1 1 d . . . . .
H11 H 0.877215 0.328754 0.279287 0.033 Uiso 1 1 calc R U . . .
C12 C 0.8357(5) 0.4801(6) 0.2009(5) 0.0243(16) Uani 1 1 d . . . . .
H12 H 0.795548 0.433996 0.155565 0.029 Uiso 1 1 calc R U . . .
C13 C 0.7438(4) 0.8650(7) 0.2467(4) 0.0222(16) Uani 1 1 d . . . . .
H13A H 0.748126 0.948856 0.273665 0.027 Uiso 1 1 calc R U . . .
H13B H 0.760567 0.802591 0.293935 0.027 Uiso 1 1 calc R U . . .
C14 C 0.6420(4) 0.8426(6) 0.1972(4) 0.0228(16) Uani 1 1 d . . . . .
H14A H 0.596414 0.845656 0.236602 0.027 Uiso 1 1 calc R U . . .
H14B H 0.622648 0.906380 0.151241 0.027 Uiso 1 1 calc R U . . .
C15 C 0.5516(4) 0.6830(6) 0.1048(4) 0.0244(16) Uani 1 1 d . . . . .
H15A H 0.528039 0.746990 0.059975 0.029 Uiso 1 1 calc R U . . .
H15B H 0.502248 0.670165 0.139760 0.029 Uiso 1 1 calc R U . . .
C16 C 0.5732(5) 0.5620(7) 0.0636(4) 0.0256(16) Uani 1 1 d . . . . .
H16A H 0.588748 0.495765 0.108160 0.031 Uiso 1 1 calc R U . . .
H16B H 0.516305 0.535150 0.019160 0.031 Uiso 1 1 calc R U . . .
C17 C 0.1970(5) 0.5128(6) 0.3006(4) 0.0226(15) Uani 1 1 d . . . . .
H17 H 0.238377 0.557433 0.345937 0.027 Uiso 1 1 calc R U . . .
C18 C 0.1519(5) 0.5761(7) 0.2273(4) 0.0263(16) Uani 1 1 d . . . . .
H18 H 0.161436 0.663252 0.222087 0.032 Uiso 1 1 calc R U . . .
C19 C 0.0923(5) 0.5106(7) 0.1614(5) 0.0289(18) Uani 1 1 d . . . . .
H19 H 0.060776 0.552208 0.109837 0.035 Uiso 1 1 calc R U . . .
C20 C 0.0792(4) 0.3853(7) 0.1709(4) 0.0248(16) Uani 1 1 d . . . . .
H20 H 0.037649 0.339697 0.126263 0.030 Uiso 1 1 calc R U . . .
C21 C 0.1265(4) 0.3251(6) 0.2457(4) 0.0171(15) Uani 1 1 d . . . . .
C22 C 0.1130(4) 0.1884(7) 0.2622(4) 0.0211(15) Uani 1 1 d . . . . .
H22A H 0.058978 0.177388 0.291981 0.025 Uiso 1 1 calc R U . . .
H22B H 0.096952 0.143001 0.206189 0.025 Uiso 1 1 calc R U . . .
C23 C 0.1873(5) 0.0178(6) 0.3605(4) 0.0207(16) Uani 1 1 d . . . . .
H23C H 0.209493 -0.052535 0.329083 0.025 Uiso 1 1 calc R U . . .
H23D H 0.117285 0.006593 0.356957 0.025 Uiso 1 1 calc R U . . .
C24 C 0.2392(4) 0.0126(6) 0.4544(4) 0.0192(16) Uani 1 1 d . . . . .
C25 C 0.2371(5) -0.0963(7) 0.5029(5) 0.0253(16) Uani 1 1 d . . . . .
H25 H 0.205639 -0.169125 0.476432 0.030 Uiso 1 1 calc R U . . .
C26 C 0.2815(5) -0.0960(7) 0.5901(5) 0.0287(17) Uani 1 1 d . . . . .
H26 H 0.279357 -0.168427 0.624478 0.034 Uiso 1 1 calc R U . . .
C27 C 0.3291(5) 0.0099(7) 0.6273(4) 0.0254(17) Uani 1 1 d . . . . .
H27 H 0.361192 0.010150 0.686775 0.030 Uiso 1 1 calc R U . . .
C28 C 0.3295(4) 0.1152(7) 0.5768(4) 0.0219(15) Uani 1 1 d . . . . .
H28 H 0.361975 0.188124 0.602147 0.026 Uiso 1 1 calc R U . . .
C29 C 0.2767(4) 0.1223(7) 0.2633(4) 0.0208(15) Uani 1 1 d . . . . .
H29A H 0.266832 0.187695 0.217852 0.025 Uiso 1 1 calc R U . . .
H29B H 0.268331 0.040096 0.233912 0.025 Uiso 1 1 calc R U . . .
C30 C 0.3774(5) 0.1319(6) 0.3170(4) 0.0226(16) Uani 1 1 d . . . . .
H30A H 0.389440 0.066363 0.362317 0.027 Uiso 1 1 calc R U . . .
H30B H 0.425294 0.122895 0.280114 0.027 Uiso 1 1 calc R U . . .
C31 C 0.4722(4) 0.2830(7) 0.4166(4) 0.0242(15) Uani 1 1 d . . . . .
H31A H 0.526460 0.287726 0.386473 0.029 Uiso 1 1 calc R U . . .
H31B H 0.486919 0.218065 0.462236 0.029 Uiso 1 1 calc R U . . .
C32 C 0.4565(4) 0.4070(6) 0.4556(4) 0.0223(15) Uani 1 1 d . . . . .
H32A H 0.511370 0.427254 0.504020 0.027 Uiso 1 1 calc R U . . .
H32B H 0.450605 0.473735 0.411267 0.027 Uiso 1 1 calc R U . . .
H1 H 0.650(6) 0.547(8) -0.012(5) 0.033 Uiso 1 1 d . U . . .
H3A H 0.907(5) 0.698(7) 0.010(4) 0.033 Uiso 1 1 d . U . . .
H3B H 0.857(5) 0.606(7) -0.009(5) 0.033 Uiso 1 1 d . U . . .
H5 H 0.366(5) 0.463(7) 0.529(4) 0.033 Uiso 1 1 d . U . . .
H23A H 0.607(5) 0.407(7) 0.837(4) 0.033 Uiso 1 1 d . U . . .
H23B H 0.541(5) 0.510(6) 0.843(4) 0.033 Uiso 1 1 d . U . . .
H24A H 0.364(5) 0.570(8) 0.643(5) 0.033 Uiso 1 1 d . U . . .
H24B H 0.279(5) 0.602(7) 0.590(4) 0.033 Uiso 1 1 d . U . . .


_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 2.086(5) . ?
Fe1 N3 2.116(5) . ?
Fe1 O3 2.124(5) . ?
Fe1 N2 2.135(5) . ?
Fe1 O2 2.162(4) . ?
Fe1 N1 2.257(5) . ?
Fe2 O5 2.067(4) . ?
Fe2 N6 2.120(6) . ?
Fe2 N5 2.121(5) . ?
Fe2 O6 2.148(4) . ?
Fe2 O4 2.160(4) . ?
Fe2 N4 2.252(5) . ?
N1 C7 1.476(7) . ?
N1 C6 1.477(9) . ?
N1 C13 1.505(8) . ?
N2 C5 1.339(8) . ?
N2 C1 1.342(8) . ?
N3 C8 1.340(8) . ?
N3 C12 1.348(9) . ?
N4 C22 1.479(7) . ?
N4 C23 1.489(8) . ?
N4 C29 1.490(8) . ?
N5 C17 1.345(8) . ?
N5 C21 1.352(8) . ?
N6 C24 1.339(8) . ?
N6 C28 1.383(8) . ?
O1 C16 1.438(8) . ?
O1 H1 0.67(7) . ?
O2 C14 1.439(8) . ?
O2 C15 1.447(7) . ?
O3 H3A 0.82(7) . ?
O3 H3B 0.78(7) . ?
O4 C31 1.440(7) . ?
O4 C30 1.447(8) . ?
O5 C32 1.442(8) . ?
O5 H5 0.97(7) . ?
O6 H6A 0.8525 . ?
O6 H6B 0.8528 . ?
O7 Cl1 1.441(5) . ?
O8 Cl1 1.423(5) . ?
O9 Cl1 1.436(5) . ?
O10 Cl1 1.425(5) . ?
O11 Cl2 1.444(4) . ?
O12 Cl2 1.429(5) . ?
O13 Cl2 1.429(5) . ?
O14 Cl2 1.448(4) . ?
O15 Cl3 1.431(5) . ?
O16 Cl3 1.426(4) . ?
O17 Cl3 1.462(4) . ?
O18 Cl3 1.425(5) . ?
O19 Cl4 1.427(5) . ?
O20 Cl4 1.439(5) . ?
O21 Cl4 1.438(6) . ?
O22 Cl4 1.428(6) . ?
O23 H23A 0.96(8) . ?
O23 H23B 0.92(7) . ?
O24 H24A 0.72(7) . ?
O24 H24B 0.99(7) . ?
C1 C2 1.360(10) . ?
C1 H1A 0.9500 . ?
C2 C3 1.394(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.369(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.516(9) . ?
C6 H6C 0.9900 . ?
C6 H6D 0.9900 . ?
C7 C8 1.509(10) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.390(9) . ?
C9 C10 1.391(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.369(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(9) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.506(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.511(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.373(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.368(10) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.506(10) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.505(9) . ?
C23 H23C 0.9900 . ?
C23 H23D 0.9900 . ?
C24 C25 1.398(10) . ?
C25 C26 1.383(10) . ?
C25 H25 0.9500 . ?
C26 C27 1.384(10) . ?
C26 H26 0.9500 . ?
C27 C28 1.381(10) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.499(8) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.500(10) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?

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 N3 105.3(2) . . ?
O1 Fe1 O3 92.7(2) . . ?
N3 Fe1 O3 93.4(2) . . ?
O1 Fe1 N2 102.47(19) . . ?
N3 Fe1 N2 152.2(2) . . ?
O3 Fe1 N2 85.9(2) . . ?
O1 Fe1 O2 76.46(17) . . ?
N3 Fe1 O2 90.84(19) . . ?
O3 Fe1 O2 169.08(18) . . ?
N2 Fe1 O2 94.97(19) . . ?
O1 Fe1 N1 154.88(19) . . ?
N3 Fe1 N1 77.0(2) . . ?
O3 Fe1 N1 112.2(2) . . ?
N2 Fe1 N1 77.55(19) . . ?
O2 Fe1 N1 78.51(17) . . ?
O5 Fe2 N6 101.60(18) . . ?
O5 Fe2 N5 107.60(19) . . ?
N6 Fe2 N5 150.8(2) . . ?
O5 Fe2 O6 90.29(17) . . ?
N6 Fe2 O6 85.1(2) . . ?
N5 Fe2 O6 93.11(19) . . ?
O5 Fe2 O4 76.25(17) . . ?
N6 Fe2 O4 95.17(19) . . ?
N5 Fe2 O4 93.27(19) . . ?
O6 Fe2 O4 166.33(16) . . ?
O5 Fe2 N4 155.00(18) . . ?
N6 Fe2 N4 77.4(2) . . ?
N5 Fe2 N4 76.9(2) . . ?
O6 Fe2 N4 114.30(19) . . ?
O4 Fe2 N4 78.96(17) . . ?
C7 N1 C6 113.5(5) . . ?
C7 N1 C13 109.4(5) . . ?
C6 N1 C13 112.0(5) . . ?
C7 N1 Fe1 106.0(4) . . ?
C6 N1 Fe1 109.5(4) . . ?
C13 N1 Fe1 106.0(4) . . ?
C5 N2 C1 118.8(6) . . ?
C5 N2 Fe1 116.6(4) . . ?
C1 N2 Fe1 123.8(5) . . ?
C8 N3 C12 118.6(5) . . ?
C8 N3 Fe1 117.0(4) . . ?
C12 N3 Fe1 123.9(4) . . ?
C22 N4 C23 113.3(5) . . ?
C22 N4 C29 109.5(5) . . ?
C23 N4 C29 111.5(5) . . ?
C22 N4 Fe2 106.8(4) . . ?
C23 N4 Fe2 110.1(4) . . ?
C29 N4 Fe2 105.2(4) . . ?
C17 N5 C21 119.3(6) . . ?
C17 N5 Fe2 123.8(4) . . ?
C21 N5 Fe2 116.6(4) . . ?
C24 N6 C28 119.1(6) . . ?
C24 N6 Fe2 118.2(4) . . ?
C28 N6 Fe2 122.1(5) . . ?
C16 O1 Fe1 115.3(4) . . ?
C16 O1 H1 110(7) . . ?
Fe1 O1 H1 134(7) . . ?
C14 O2 C15 114.3(5) . . ?
C14 O2 Fe1 109.8(4) . . ?
C15 O2 Fe1 110.6(4) . . ?
Fe1 O3 H3A 127(5) . . ?
Fe1 O3 H3B 116(6) . . ?
H3A O3 H3B 99(7) . . ?
C31 O4 C30 115.8(5) . . ?
C31 O4 Fe2 110.1(4) . . ?
C30 O4 Fe2 109.7(4) . . ?
C32 O5 Fe2 116.4(4) . . ?
C32 O5 H5 110(4) . . ?
Fe2 O5 H5 131(4) . . ?
Fe2 O6 H6A 108.9 . . ?
Fe2 O6 H6B 109.4 . . ?
H6A O6 H6B 104.4 . . ?
H23A O23 H23B 103(5) . . ?
H24A O24 H24B 104(7) . . ?
O8 Cl1 O10 110.3(4) . . ?
O8 Cl1 O9 109.3(3) . . ?
O10 Cl1 O9 111.3(3) . . ?
O8 Cl1 O7 110.1(3) . . ?
O10 Cl1 O7 107.8(3) . . ?
O9 Cl1 O7 108.1(3) . . ?
O12 Cl2 O13 110.3(3) . . ?
O12 Cl2 O11 110.1(3) . . ?
O13 Cl2 O11 109.8(3) . . ?
O12 Cl2 O14 109.1(3) . . ?
O13 Cl2 O14 108.8(3) . . ?
O11 Cl2 O14 108.6(3) . . ?
O18 Cl3 O16 110.9(3) . . ?
O18 Cl3 O15 110.6(3) . . ?
O16 Cl3 O15 109.7(3) . . ?
O18 Cl3 O17 108.2(3) . . ?
O16 Cl3 O17 108.4(3) . . ?
O15 Cl3 O17 109.0(3) . . ?
O19 Cl4 O22 109.5(3) . . ?
O19 Cl4 O21 109.9(3) . . ?
O22 Cl4 O21 109.6(4) . . ?
O19 Cl4 O20 109.1(3) . . ?
O22 Cl4 O20 109.0(3) . . ?
O21 Cl4 O20 109.7(3) . . ?
N2 C1 C2 123.5(7) . . ?
N2 C1 H1A 118.3 . . ?
C2 C1 H1A 118.3 . . ?
C1 C2 C3 117.9(6) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 119.2(7) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 119.7(7) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N2 C5 C4 120.8(6) . . ?
N2 C5 C6 118.6(6) . . ?
C4 C5 C6 120.5(6) . . ?
N1 C6 C5 113.1(5) . . ?
N1 C6 H6C 109.0 . . ?
C5 C6 H6C 109.0 . . ?
N1 C6 H6D 109.0 . . ?
C5 C6 H6D 109.0 . . ?
H6C C6 H6D 107.8 . . ?
N1 C7 C8 110.5(5) . . ?
N1 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N3 C8 C9 122.0(6) . . ?
N3 C8 C7 115.9(6) . . ?
C9 C8 C7 122.1(6) . . ?
C8 C9 C10 118.3(6) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C11 C10 C9 120.2(6) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 118.1(7) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
N3 C12 C11 122.7(6) . . ?
N3 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
N1 C13 C14 111.7(5) . . ?
N1 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N1 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
O2 C14 C13 105.5(5) . . ?
O2 C14 H14A 110.6 . . ?
C13 C14 H14A 110.6 . . ?
O2 C14 H14B 110.6 . . ?
C13 C14 H14B 110.6 . . ?
H14A C14 H14B 108.8 . . ?
O2 C15 C16 104.8(5) . . ?
O2 C15 H15A 110.8 . . ?
C16 C15 H15A 110.8 . . ?
O2 C15 H15B 110.8 . . ?
C16 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
O1 C16 C15 108.0(5) . . ?
O1 C16 H16A 110.1 . . ?
C15 C16 H16A 110.1 . . ?
O1 C16 H16B 110.1 . . ?
C15 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
N5 C17 C18 122.1(6) . . ?
N5 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C17 C18 C19 118.7(7) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C20 C19 C18 119.4(6) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 119.9(6) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
N5 C21 C20 120.5(6) . . ?
N5 C21 C22 116.5(6) . . ?
C20 C21 C22 122.9(6) . . ?
N4 C22 C21 109.8(5) . . ?
N4 C22 H22A 109.7 . . ?
C21 C22 H22A 109.7 . . ?
N4 C22 H22B 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
N4 C23 C24 113.5(5) . . ?
N4 C23 H23C 108.9 . . ?
C24 C23 H23C 108.9 . . ?
N4 C23 H23D 108.9 . . ?
C24 C23 H23D 108.9 . . ?
H23C C23 H23D 107.7 . . ?
N6 C24 C25 121.8(6) . . ?
N6 C24 C23 117.9(6) . . ?
C25 C24 C23 120.3(6) . . ?
C26 C25 C24 118.9(7) . . ?
C26 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C25 C26 C27 119.8(7) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C28 C27 C26 119.2(6) . . ?
C28 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
C27 C28 N6 121.2(6) . . ?
C27 C28 H28 119.4 . . ?
N6 C28 H28 119.4 . . ?
N4 C29 C30 112.1(5) . . ?
N4 C29 H29A 109.2 . . ?
C30 C29 H29A 109.2 . . ?
N4 C29 H29B 109.2 . . ?
C30 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
O4 C30 C29 105.2(5) . . ?
O4 C30 H30A 110.7 . . ?
C29 C30 H30A 110.7 . . ?
O4 C30 H30B 110.7 . . ?
C29 C30 H30B 110.7 . . ?
H30A C30 H30B 108.8 . . ?
O4 C31 C32 105.7(5) . . ?
O4 C31 H31A 110.6 . . ?
C32 C31 H31A 110.6 . . ?
O4 C31 H31B 110.6 . . ?
C32 C31 H31B 110.6 . . ?
H31A C31 H31B 108.7 . . ?
O5 C32 C31 106.9(5) . . ?
O5 C32 H32A 110.3 . . ?
C31 C32 H32A 110.3 . . ?
O5 C32 H32B 110.3 . . ?
C31 C32 H32B 110.3 . . ?
H32A C32 H32B 108.6 . . ?

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
C5 N2 C1 C2 0.7(10) . . . . ?
Fe1 N2 C1 C2 -169.0(5) . . . . ?
N2 C1 C2 C3 -0.5(11) . . . . ?
C1 C2 C3 C4 -0.6(11) . . . . ?
C2 C3 C4 C5 1.4(11) . . . . ?
C1 N2 C5 C4 0.2(10) . . . . ?
Fe1 N2 C5 C4 170.6(5) . . . . ?
C1 N2 C5 C6 -177.6(6) . . . . ?
Fe1 N2 C5 C6 -7.1(8) . . . . ?
C3 C4 C5 N2 -1.2(11) . . . . ?
C3 C4 C5 C6 176.5(7) . . . . ?
C7 N1 C6 C5 139.1(6) . . . . ?
C13 N1 C6 C5 -96.4(7) . . . . ?
Fe1 N1 C6 C5 20.9(7) . . . . ?
N2 C5 C6 N1 -10.4(9) . . . . ?
C4 C5 C6 N1 171.9(6) . . . . ?
C6 N1 C7 C8 -159.4(6) . . . . ?
C13 N1 C7 C8 74.7(7) . . . . ?
Fe1 N1 C7 C8 -39.2(6) . . . . ?
C12 N3 C8 C9 -0.6(10) . . . . ?
Fe1 N3 C8 C9 171.8(5) . . . . ?
C12 N3 C8 C7 178.6(6) . . . . ?
Fe1 N3 C8 C7 -9.0(8) . . . . ?
N1 C7 C8 N3 34.1(8) . . . . ?
N1 C7 C8 C9 -146.7(6) . . . . ?
N3 C8 C9 C10 0.9(11) . . . . ?
C7 C8 C9 C10 -178.3(7) . . . . ?
C8 C9 C10 C11 -0.8(11) . . . . ?
C9 C10 C11 C12 0.6(11) . . . . ?
C8 N3 C12 C11 0.3(10) . . . . ?
Fe1 N3 C12 C11 -171.5(5) . . . . ?
C10 C11 C12 N3 -0.3(11) . . . . ?
C7 N1 C13 C14 -148.0(6) . . . . ?
C6 N1 C13 C14 85.3(6) . . . . ?
Fe1 N1 C13 C14 -34.1(6) . . . . ?
C15 O2 C14 C13 -176.9(5) . . . . ?
Fe1 O2 C14 C13 -52.0(5) . . . . ?
N1 C13 C14 O2 58.2(7) . . . . ?
C14 O2 C15 C16 172.4(5) . . . . ?
Fe1 O2 C15 C16 47.9(5) . . . . ?
Fe1 O1 C16 C15 34.3(6) . . . . ?
O2 C15 C16 O1 -52.7(6) . . . . ?
C21 N5 C17 C18 0.6(10) . . . . ?
Fe2 N5 C17 C18 174.0(5) . . . . ?
N5 C17 C18 C19 -0.4(11) . . . . ?
C17 C18 C19 C20 0.6(11) . . . . ?
C18 C19 C20 C21 -0.9(11) . . . . ?
C17 N5 C21 C20 -0.9(9) . . . . ?
Fe2 N5 C21 C20 -174.7(5) . . . . ?
C17 N5 C21 C22 -177.9(6) . . . . ?
Fe2 N5 C21 C22 8.2(7) . . . . ?
C19 C20 C21 N5 1.1(10) . . . . ?
C19 C20 C21 C22 177.9(7) . . . . ?
C23 N4 C22 C21 160.6(6) . . . . ?
C29 N4 C22 C21 -74.3(7) . . . . ?
Fe2 N4 C22 C21 39.2(6) . . . . ?
N5 C21 C22 N4 -33.3(8) . . . . ?
C20 C21 C22 N4 149.8(6) . . . . ?
C22 N4 C23 C24 -135.8(6) . . . . ?
C29 N4 C23 C24 100.1(6) . . . . ?
Fe2 N4 C23 C24 -16.2(7) . . . . ?
C28 N6 C24 C25 1.1(10) . . . . ?
Fe2 N6 C24 C25 -170.0(5) . . . . ?
C28 N6 C24 C23 178.3(6) . . . . ?
Fe2 N6 C24 C23 7.2(8) . . . . ?
N4 C23 C24 N6 7.0(9) . . . . ?
N4 C23 C24 C25 -175.8(6) . . . . ?
N6 C24 C25 C26 0.3(10) . . . . ?
C23 C24 C25 C26 -176.8(6) . . . . ?
C24 C25 C26 C27 -1.6(10) . . . . ?
C25 C26 C27 C28 1.6(11) . . . . ?
C26 C27 C28 N6 -0.2(11) . . . . ?
C24 N6 C28 C27 -1.2(10) . . . . ?
Fe2 N6 C28 C27 169.5(5) . . . . ?
C22 N4 C29 C30 152.1(6) . . . . ?
C23 N4 C29 C30 -81.7(7) . . . . ?
Fe2 N4 C29 C30 37.6(6) . . . . ?
C31 O4 C30 C29 175.4(5) . . . . ?
Fe2 O4 C30 C29 50.0(5) . . . . ?
N4 C29 C30 O4 -59.8(7) . . . . ?
C30 O4 C31 C32 -173.3(5) . . . . ?
Fe2 O4 C31 C32 -48.2(6) . . . . ?
Fe2 O5 C32 C31 -33.4(6) . . . . ?
O4 C31 C32 O5 52.1(6) . . . . ?

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
O5 H5 O24 0.97(7) 1.64(7) 2.609(7) 173(6) .
O23 H23A O14 0.96(8) 1.93(8) 2.860(7) 163(6) .
O23 H23A Cl2 0.96(8) 2.80(8) 3.713(5) 160(5) .
O23 H23B O17 0.92(7) 1.99(7) 2.907(6) 177(6) .
O23 H23B Cl3 0.92(7) 2.93(7) 3.752(5) 150(5) .
O24 H24A O17 0.72(7) 2.13(7) 2.838(6) 169(9) .
O6 H6A O7 0.85 2.00 2.839(7) 167.0 2_656
O6 H6A Cl1 0.85 2.83 3.526(5) 140.3 2_656
O24 H24B O7 0.99(7) 2.04(6) 2.918(6) 147(5) 2_656
O24 H24B Cl1 0.99(7) 2.93(7) 3.879(5) 161(5) 2_656
O3 H3A O21 0.82(7) 2.03(7) 2.844(8) 173(7) 1_655
O1 H1 O23 0.67(7) 1.97(7) 2.608(6) 160(9) 1_554
O3 H3B O20 0.78(7) 2.42(7) 3.023(8) 135(7) 2_645
O3 H3B O22 0.78(7) 2.14(8) 2.900(8) 164(7) 2_645
O3 H3B Cl4 0.78(7) 2.76(8) 3.520(5) 165(7) 2_645

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.080



####################################################################### 
# 
# 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_pre2_a
_database_code_depnum_ccdc_archive 'CCDC 1999287'
loop_
_audit_author_name
_audit_author_address
'Jin Kim'
;Sunchon National University
South Korea
;
_audit_update_record             
;
2020-04-26 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H42 Fe2 N6 O5, 4(Cl O4), 2(H2 O)'
_chemical_formula_sum            'C32 H46 Cl4 Fe2 N6 O23'
_chemical_formula_weight         1136.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   15.9079(12)
_cell_length_b                   17.3412(13)
_cell_length_c                   16.1343(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.7240(10)
_cell_angle_gamma                90
_cell_volume                     4450.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    15854
_cell_measurement_theta_min      1.737
_cell_measurement_theta_max      25.018

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_F_000             2336
_exptl_transmission_factor_min   0.689
_exptl_transmission_factor_max   0.745
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.985
_shelx_estimated_absorpt_T_min   0.694
_shelx_estimated_absorpt_T_max   0.827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15854
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.737
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_full        25.018
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3913
_reflns_number_gt                3589
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+8.1594P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3913
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0817
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.38906(2) 0.74121(2) 0.74760(2) 0.01141(10) Uani 1 1 d . . . . .
N1 N 0.38628(10) 0.78526(11) 0.62350(10) 0.0168(4) Uani 1 1 d . . . . .
N2 N 0.33575(10) 0.85598(10) 0.76411(10) 0.0152(4) Uani 1 1 d . . . . .
N3 N 0.37078(10) 0.74650(10) 0.87763(11) 0.0138(4) Uani 1 1 d . . . . .
O1 O 0.500000 0.75453(11) 0.750000 0.0160(4) Uani 1 2 d S T P . .
O2 O 0.25460(9) 0.71941(9) 0.73328(9) 0.0183(3) Uani 1 1 d . . . . .
O3 O 0.38093(9) 0.62780(9) 0.72590(9) 0.0187(3) Uani 1 1 d . . . . .
O4 O 0.27722(12) 0.48979(11) 0.40636(11) 0.0389(5) Uani 1 1 d . . . . .
O5 O 0.30082(12) 0.60720(10) 0.47497(12) 0.0388(5) Uani 1 1 d . . . . .
O6 O 0.39546(11) 0.50417(12) 0.49266(11) 0.0413(5) Uani 1 1 d . . . . .
O7 O 0.26103(13) 0.49843(12) 0.54954(11) 0.0438(5) Uani 1 1 d . . . . .
O8 O 0.56532(10) 0.43840(10) 0.71647(12) 0.0339(4) Uani 1 1 d . . . . .
O9 O 0.46438(12) 0.34264(12) 0.68591(11) 0.0400(5) Uani 1 1 d . . . . .
O10 O 0.5593(3) 0.1314(3) 0.7904(2) 0.172(2) Uani 1 1 d . . . . .
O11 O 0.45893(14) 0.04047(11) 0.80959(11) 0.0435(5) Uani 1 1 d . . . . .
O12 O 0.48275(11) 0.56002(10) 0.63385(11) 0.0256(4) Uani 1 1 d G . . . .
Cl1 Cl 0.30851(3) 0.52536(3) 0.48064(3) 0.01978(13) Uani 1 1 d . . . . .
Cl2 Cl 0.500000 0.38945(4) 0.750000 0.02072(17) Uani 1 2 d S T P . .
Cl3 Cl 0.500000 0.08721(4) 0.750000 0.02732(19) Uani 1 2 d S T P . .
C1 C 0.40579(13) 0.74395(14) 0.55553(14) 0.0212(5) Uani 1 1 d . . . . .
H1 H 0.405604 0.689250 0.558845 0.025 Uiso 1 1 calc R U . . .
C2 C 0.42596(14) 0.77846(16) 0.48146(14) 0.0273(5) Uani 1 1 d . . . . .
H2 H 0.439231 0.748200 0.434318 0.033 Uiso 1 1 calc R U . . .
C3 C 0.42647(14) 0.85810(16) 0.47726(14) 0.0302(6) Uani 1 1 d . . . . .
H3A H 0.441172 0.883288 0.427202 0.036 Uiso 1 1 calc R U . . .
C4 C 0.40558(14) 0.90068(15) 0.54596(14) 0.0267(5) Uani 1 1 d . . . . .
H4 H 0.404904 0.955414 0.543597 0.032 Uiso 1 1 calc R U . . .
C5 C 0.38550(12) 0.86259(13) 0.61879(13) 0.0186(4) Uani 1 1 d . . . . .
C6 C 0.36748(14) 0.90676(13) 0.69687(13) 0.0218(5) Uani 1 1 d . . . . .
H6A H 0.419572 0.932682 0.716258 0.026 Uiso 1 1 calc R U . . .
H6B H 0.325139 0.947132 0.684546 0.026 Uiso 1 1 calc R U . . .
C7 C 0.36571(13) 0.88316(12) 0.84707(12) 0.0177(4) Uani 1 1 d . . . . .
H7A H 0.330316 0.926635 0.865692 0.021 Uiso 1 1 calc R U . . .
H7B H 0.424375 0.901736 0.843154 0.021 Uiso 1 1 calc R U . . .
C8 C 0.36136(12) 0.81818(12) 0.90908(13) 0.0155(4) Uani 1 1 d . . . . .
C9 C 0.35318(13) 0.83076(13) 0.99350(13) 0.0193(5) Uani 1 1 d . . . . .
H9 H 0.344813 0.881374 1.014368 0.023 Uiso 1 1 calc R U . . .
C10 C 0.35743(14) 0.76800(13) 1.04705(14) 0.0215(5) Uani 1 1 d . . . . .
H10 H 0.353374 0.775388 1.105207 0.026 Uiso 1 1 calc R U . . .
C11 C 0.36762(13) 0.69472(13) 1.01484(13) 0.0201(5) Uani 1 1 d . . . . .
H11 H 0.370524 0.651163 1.050472 0.024 Uiso 1 1 calc R U . . .
C12 C 0.37351(12) 0.68588(12) 0.92993(13) 0.0166(4) Uani 1 1 d . . . . .
H12 H 0.379685 0.635484 0.907743 0.020 Uiso 1 1 calc R U . . .
C13 C 0.24142(13) 0.85100(13) 0.76350(14) 0.0221(5) Uani 1 1 d . . . . .
H13A H 0.217626 0.900981 0.745055 0.027 Uiso 1 1 calc R U . . .
H13B H 0.221849 0.841100 0.820525 0.027 Uiso 1 1 calc R U . . .
C14 C 0.20962(13) 0.78781(14) 0.70687(14) 0.0228(5) Uani 1 1 d . . . . .
H14A H 0.148235 0.780737 0.712804 0.027 Uiso 1 1 calc R U . . .
H14B H 0.221749 0.800012 0.648288 0.027 Uiso 1 1 calc R U . . .
C15 C 0.23884(14) 0.65085(14) 0.68490(14) 0.0237(5) Uani 1 1 d . . . . .
H15A H 0.250391 0.660040 0.625566 0.028 Uiso 1 1 calc R U . . .
H15B H 0.179852 0.633632 0.690523 0.028 Uiso 1 1 calc R U . . .
C16 C 0.29855(14) 0.59243(13) 0.72076(14) 0.0231(5) Uani 1 1 d . . . . .
H16A H 0.280056 0.576554 0.776576 0.028 Uiso 1 1 calc R U . . .
H16B H 0.300302 0.546139 0.684913 0.028 Uiso 1 1 calc R U . . .
H3 H 0.4168(17) 0.6047(16) 0.6985(17) 0.028 Uiso 1 1 d . U . . .
H12A H 0.4650(17) 0.5446(16) 0.5924(18) 0.028 Uiso 1 1 d . U . . .
H12B H 0.5112(17) 0.5257(17) 0.6566(17) 0.028 Uiso 1 1 d . U . . .


_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 1.7799(4) . ?
Fe1 O3 2.0014(16) . ?
Fe1 N3 2.1235(18) . ?
Fe1 N1 2.1431(17) . ?
Fe1 N2 2.1811(17) . ?
Fe1 O2 2.1815(14) . ?
N1 C5 1.343(3) . ?
N1 C1 1.349(3) . ?
N2 C6 1.490(3) . ?
N2 C7 1.492(3) . ?
N2 C13 1.503(3) . ?
N3 C12 1.348(3) . ?
N3 C8 1.352(3) . ?
O2 C15 1.442(3) . ?
O2 C14 1.447(3) . ?
O3 C16 1.448(3) . ?
O3 H3 0.83(3) . ?
O4 Cl1 1.4317(17) . ?
O5 Cl1 1.4273(18) . ?
O6 Cl1 1.4419(17) . ?
O7 Cl1 1.4302(18) . ?
O8 Cl2 1.4515(17) . ?
O9 Cl2 1.4263(18) . ?
O10 Cl3 1.373(3) . ?
O11 Cl3 1.4226(18) . ?
O12 H12A 0.77(3) . ?
O12 H12B 0.83(3) . ?
C1 C2 1.378(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.505(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.509(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.387(3) . ?
C9 C10 1.391(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.510(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.500(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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 O3 101.14(8) . . ?
O1 Fe1 N3 96.95(5) . . ?
O3 Fe1 N3 101.88(6) . . ?
O1 Fe1 N1 89.01(5) . . ?
O3 Fe1 N1 100.74(7) . . ?
N3 Fe1 N1 154.98(7) . . ?
O1 Fe1 N2 105.41(8) . . ?
O3 Fe1 N2 153.34(6) . . ?
N3 Fe1 N2 77.39(6) . . ?
N1 Fe1 N2 77.60(7) . . ?
O1 Fe1 O2 174.53(5) . . ?
O3 Fe1 O2 75.53(6) . . ?
N3 Fe1 O2 88.05(6) . . ?
N1 Fe1 O2 87.37(6) . . ?
N2 Fe1 O2 77.81(6) . . ?
C5 N1 C1 119.09(19) . . ?
C5 N1 Fe1 114.13(14) . . ?
C1 N1 Fe1 124.60(15) . . ?
C6 N2 C7 111.05(16) . . ?
C6 N2 C13 112.12(16) . . ?
C7 N2 C13 109.38(16) . . ?
C6 N2 Fe1 108.33(12) . . ?
C7 N2 Fe1 106.11(12) . . ?
C13 N2 Fe1 109.66(13) . . ?
C12 N3 C8 119.00(18) . . ?
C12 N3 Fe1 125.51(14) . . ?
C8 N3 Fe1 115.33(13) . . ?
Fe1 O1 Fe1 165.08(13) . 2_656 ?
C15 O2 C14 115.76(16) . . ?
C15 O2 Fe1 111.32(12) . . ?
C14 O2 Fe1 111.71(12) . . ?
C16 O3 Fe1 118.85(13) . . ?
C16 O3 H3 113.1(19) . . ?
Fe1 O3 H3 121.7(19) . . ?
H12A O12 H12B 109(3) . . ?
O5 Cl1 O7 109.21(12) . . ?
O5 Cl1 O4 110.25(12) . . ?
O7 Cl1 O4 109.17(12) . . ?
O5 Cl1 O6 110.08(12) . . ?
O7 Cl1 O6 109.11(12) . . ?
O4 Cl1 O6 109.00(11) . . ?
O9 Cl2 O9 110.61(17) . 2_656 ?
O9 Cl2 O8 110.02(11) . . ?
O9 Cl2 O8 108.87(11) 2_656 . ?
O9 Cl2 O8 108.86(10) . 2_656 ?
O9 Cl2 O8 110.02(11) 2_656 2_656 ?
O8 Cl2 O8 108.43(15) . 2_656 ?
O10 Cl3 O10 112.1(5) . 2_656 ?
O10 Cl3 O11 108.68(19) . 2_656 ?
O10 Cl3 O11 108.4(2) 2_656 2_656 ?
O10 Cl3 O11 108.4(2) . . ?
O10 Cl3 O11 108.68(19) 2_656 . ?
O11 Cl3 O11 110.54(16) 2_656 . ?
N1 C1 C2 122.2(2) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C1 C2 C3 118.5(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 121.4(2) . . ?
N1 C5 C6 117.54(18) . . ?
C4 C5 C6 121.0(2) . . ?
N2 C6 C5 112.25(18) . . ?
N2 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C8 110.01(17) . . ?
N2 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
N2 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N3 C8 C9 121.71(19) . . ?
N3 C8 C7 115.57(18) . . ?
C9 C8 C7 122.62(19) . . ?
C8 C9 C10 118.8(2) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 118.9(2) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
N3 C12 C11 122.1(2) . . ?
N3 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
N2 C13 C14 111.87(17) . . ?
N2 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N2 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
O2 C14 C13 104.84(17) . . ?
O2 C14 H14A 110.8 . . ?
C13 C14 H14A 110.8 . . ?
O2 C14 H14B 110.8 . . ?
C13 C14 H14B 110.8 . . ?
H14A C14 H14B 108.9 . . ?
O2 C15 C16 104.07(17) . . ?
O2 C15 H15A 110.9 . . ?
C16 C15 H15A 110.9 . . ?
O2 C15 H15B 110.9 . . ?
C16 C15 H15B 110.9 . . ?
H15A C15 H15B 109.0 . . ?
O3 C16 C15 107.71(17) . . ?
O3 C16 H16A 110.2 . . ?
C15 C16 H16A 110.2 . . ?
O3 C16 H16B 110.2 . . ?
C15 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?

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
O3 Fe1 O1 Fe1 -10.18(4) . . . 2_656 ?
N3 Fe1 O1 Fe1 93.44(5) . . . 2_656 ?
N1 Fe1 O1 Fe1 -110.93(5) . . . 2_656 ?
N2 Fe1 O1 Fe1 172.22(5) . . . 2_656 ?
C5 N1 C1 C2 0.8(3) . . . . ?
Fe1 N1 C1 C2 -161.42(16) . . . . ?
N1 C1 C2 C3 0.3(3) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C1 N1 C5 C4 -1.0(3) . . . . ?
Fe1 N1 C5 C4 162.98(16) . . . . ?
C1 N1 C5 C6 -177.17(18) . . . . ?
Fe1 N1 C5 C6 -13.2(2) . . . . ?
C3 C4 C5 N1 0.2(3) . . . . ?
C3 C4 C5 C6 176.2(2) . . . . ?
C7 N2 C6 C5 145.74(17) . . . . ?
C13 N2 C6 C5 -91.6(2) . . . . ?
Fe1 N2 C6 C5 29.6(2) . . . . ?
N1 C5 C6 N2 -11.9(3) . . . . ?
C4 C5 C6 N2 171.96(18) . . . . ?
C6 N2 C7 C8 -159.18(16) . . . . ?
C13 N2 C7 C8 76.5(2) . . . . ?
Fe1 N2 C7 C8 -41.67(17) . . . . ?
C12 N3 C8 C9 -1.0(3) . . . . ?
Fe1 N3 C8 C9 -176.70(15) . . . . ?
C12 N3 C8 C7 175.42(17) . . . . ?
Fe1 N3 C8 C7 -0.3(2) . . . . ?
N2 C7 C8 N3 29.3(2) . . . . ?
N2 C7 C8 C9 -154.36(18) . . . . ?
N3 C8 C9 C10 2.0(3) . . . . ?
C7 C8 C9 C10 -174.14(19) . . . . ?
C8 C9 C10 C11 -1.6(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C8 N3 C12 C11 -0.5(3) . . . . ?
Fe1 N3 C12 C11 174.73(15) . . . . ?
C10 C11 C12 N3 0.9(3) . . . . ?
C6 N2 C13 C14 87.5(2) . . . . ?
C7 N2 C13 C14 -148.89(18) . . . . ?
Fe1 N2 C13 C14 -32.9(2) . . . . ?
C15 O2 C14 C13 -176.43(16) . . . . ?
Fe1 O2 C14 C13 -47.64(18) . . . . ?
N2 C13 C14 O2 53.0(2) . . . . ?
C14 O2 C15 C16 174.99(16) . . . . ?
Fe1 O2 C15 C16 46.01(18) . . . . ?
Fe1 O3 C16 C15 32.5(2) . . . . ?
O2 C15 C16 O3 -49.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O12 0.83(3) 1.68(3) 2.504(2) 174(3) .
O12 H12A O6 0.77(3) 2.06(3) 2.824(3) 169(3) .
O12 H12B O8 0.83(3) 1.99(3) 2.812(3) 173(3) .
O12 H12B Cl2 0.83(3) 2.81(3) 3.5104(19) 143(2) .

_refine_diff_density_max         1.101
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.137



####################################################################### 
# 
# 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_pre2
_database_code_depnum_ccdc_archive 'CCDC 1999288'
loop_
_audit_author_name
_audit_author_address
'Jin Kim'
;Sunchon National University
South Korea
;
_audit_update_record             
;
2020-04-26 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 Cl2 Mn N3 O2'
_chemical_formula_sum            'C16 H21 Cl2 Mn N3 O2'
_chemical_formula_weight         413.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   14.289(4)
_cell_length_b                   8.933(2)
_cell_length_c                   28.022(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3576.8(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    23624
_cell_measurement_theta_min      1.453
_cell_measurement_theta_max      25.017

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             1704
_exptl_transmission_factor_min   0.591
_exptl_transmission_factor_max   0.745
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.051
_shelx_estimated_absorpt_T_min   0.679
_shelx_estimated_absorpt_T_max   0.817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23624
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.453
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_full        25.017
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6188
_reflns_number_gt                5717
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.957
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+1.8257P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.56(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6188
_refine_ls_number_parameters     440
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.35077(6) 0.59742(10) 0.46718(3) 0.0122(2) Uani 1 1 d . . . . .
Mn2 Mn 0.37442(6) 0.09744(10) 0.70340(3) 0.0127(2) Uani 1 1 d . . . . .
Cl1 Cl 0.44516(12) 0.58268(18) 0.53800(5) 0.0236(4) Uani 1 1 d . . . . .
Cl2 Cl 0.45377(11) 0.50241(17) 0.40414(6) 0.0200(4) Uani 1 1 d . . . . .
Cl3 Cl 0.28074(11) 0.08512(18) 0.63222(5) 0.0224(4) Uani 1 1 d . . . . .
Cl4 Cl 0.27096(11) 0.00169(17) 0.76650(6) 0.0189(3) Uani 1 1 d . . . . .
N1 N 0.2654(3) 0.3872(5) 0.4714(2) 0.0139(11) Uani 1 1 d . . . . .
N2 N 0.2251(4) 0.6314(6) 0.41388(17) 0.0140(11) Uani 1 1 d . . . . .
N3 N 0.3609(3) 0.8329(6) 0.43985(19) 0.0148(12) Uani 1 1 d . . . . .
N4 N 0.4589(3) -0.1142(5) 0.6985(2) 0.0139(11) Uani 1 1 d . . . . .
N5 N 0.4995(4) 0.1277(6) 0.75652(17) 0.0142(11) Uani 1 1 d . . . . .
N6 N 0.3668(4) 0.3331(6) 0.73213(19) 0.0153(12) Uani 1 1 d . . . . .
O1 O 0.2256(3) 0.6977(5) 0.51136(15) 0.0213(10) Uani 1 1 d . . . . .
O2 O 0.2562(4) 0.5337(6) 0.60037(19) 0.0370(13) Uani 1 1 d D . . . .
O3 O 0.5009(3) 0.1968(5) 0.65953(15) 0.0218(10) Uani 1 1 d . . . . .
O4 O 0.4699(4) 0.0323(6) 0.5703(2) 0.0366(13) Uani 1 1 d . . . . .
C1 C 0.2692(5) 0.2861(7) 0.5072(2) 0.0169(14) Uani 1 1 d . . . . .
H1 H 0.313511 0.300773 0.532034 0.020 Uiso 1 1 calc R U . . .
C2 C 0.2118(5) 0.1628(7) 0.5091(2) 0.0226(15) Uani 1 1 d . . . . .
H2A H 0.215857 0.094695 0.535086 0.027 Uiso 1 1 calc R U . . .
C3 C 0.1482(5) 0.1393(7) 0.4730(2) 0.0196(14) Uani 1 1 d . . . . .
H3 H 0.107695 0.054979 0.473495 0.024 Uiso 1 1 calc R U . . .
C4 C 0.1445(4) 0.2421(7) 0.4355(2) 0.0175(13) Uani 1 1 d . . . . .
H4A H 0.102095 0.227471 0.409865 0.021 Uiso 1 1 calc R U . . .
C5 C 0.2024(4) 0.3642(7) 0.4360(2) 0.0138(13) Uani 1 1 d . . . . .
C6 C 0.2030(5) 0.4795(7) 0.3963(2) 0.0181(14) Uani 1 1 d . . . . .
H6A H 0.249818 0.450046 0.372042 0.022 Uiso 1 1 calc R U . . .
H6B H 0.140808 0.480841 0.380725 0.022 Uiso 1 1 calc R U . . .
C7 C 0.2636(5) 0.7294(7) 0.3759(2) 0.0186(14) Uani 1 1 d . . . . .
H7A H 0.211969 0.768187 0.355838 0.022 Uiso 1 1 calc R U . . .
H7B H 0.306270 0.670897 0.355190 0.022 Uiso 1 1 calc R U . . .
C8 C 0.3165(5) 0.8592(6) 0.3980(2) 0.0159(13) Uani 1 1 d . . . . .
C9 C 0.3182(5) 0.9997(7) 0.3762(2) 0.0204(15) Uani 1 1 d . . . . .
H9 H 0.284535 1.016923 0.347445 0.024 Uiso 1 1 calc R U . . .
C10 C 0.3693(5) 1.1130(7) 0.3970(3) 0.0225(16) Uani 1 1 d . . . . .
H10 H 0.374046 1.208038 0.381981 0.027 Uiso 1 1 calc R U . . .
C11 C 0.4135(5) 1.0865(7) 0.4398(2) 0.0205(15) Uani 1 1 d . . . . .
H11 H 0.447685 1.164034 0.455163 0.025 Uiso 1 1 calc R U . . .
C12 C 0.4075(4) 0.9434(7) 0.4606(2) 0.0151(14) Uani 1 1 d . . . . .
H12 H 0.437648 0.925592 0.490320 0.018 Uiso 1 1 calc R U . . .
C13 C 0.1441(4) 0.7038(7) 0.4375(2) 0.0193(14) Uani 1 1 d . . . . .
H13A H 0.086046 0.672077 0.421120 0.023 Uiso 1 1 calc R U . . .
H13B H 0.149778 0.813689 0.433800 0.023 Uiso 1 1 calc R U . . .
C14 C 0.1357(5) 0.6669(8) 0.4905(2) 0.0216(14) Uani 1 1 d . . . . .
H14A H 0.086770 0.729489 0.505562 0.026 Uiso 1 1 calc R U . . .
H14B H 0.118940 0.560235 0.494899 0.026 Uiso 1 1 calc R U . . .
C15 C 0.2243(5) 0.7672(8) 0.5577(2) 0.0233(15) Uani 1 1 d . . . . .
H15A H 0.179053 0.851023 0.557285 0.028 Uiso 1 1 calc R U . . .
H15B H 0.287026 0.809546 0.564349 0.028 Uiso 1 1 calc R U . . .
C16 C 0.1984(5) 0.6609(8) 0.5975(3) 0.0288(16) Uani 1 1 d . . . . .
H16A H 0.201391 0.715461 0.628172 0.035 Uiso 1 1 calc R U . . .
H16B H 0.132918 0.627857 0.592756 0.035 Uiso 1 1 calc R U . . .
C17 C 0.4548(5) -0.2114(7) 0.6626(2) 0.0189(14) Uani 1 1 d . . . . .
H17 H 0.411650 -0.193566 0.637478 0.023 Uiso 1 1 calc R U . . .
C18 C 0.5116(5) -0.3388(7) 0.6604(2) 0.0205(15) Uani 1 1 d . . . . .
H18 H 0.506706 -0.406990 0.634537 0.025 Uiso 1 1 calc R U . . .
C19 C 0.5751(5) -0.3630(7) 0.6971(3) 0.0221(14) Uani 1 1 d . . . . .
H19 H 0.615226 -0.447812 0.696503 0.027 Uiso 1 1 calc R U . . .
C20 C 0.5793(5) -0.2621(7) 0.7345(2) 0.0180(13) Uani 1 1 d . . . . .
H20 H 0.621779 -0.277207 0.760080 0.022 Uiso 1 1 calc R U . . .
C21 C 0.5202(5) -0.1376(7) 0.7340(2) 0.0159(13) Uani 1 1 d . . . . .
C22 C 0.5199(4) -0.0236(6) 0.7744(2) 0.0155(13) Uani 1 1 d . . . . .
H22A H 0.472153 -0.052283 0.798293 0.019 Uiso 1 1 calc R U . . .
H22B H 0.581715 -0.023713 0.790323 0.019 Uiso 1 1 calc R U . . .
C23 C 0.4628(4) 0.2253(7) 0.7945(2) 0.0154(13) Uani 1 1 d . . . . .
H23A H 0.515178 0.261595 0.814485 0.019 Uiso 1 1 calc R U . . .
H23B H 0.419655 0.167544 0.815071 0.019 Uiso 1 1 calc R U . . .
C24 C 0.4110(4) 0.3585(7) 0.7730(2) 0.0146(13) Uani 1 1 d . . . . .
C25 C 0.4067(5) 0.4962(7) 0.7964(2) 0.0213(15) Uani 1 1 d . . . . .
H25 H 0.438025 0.510985 0.825988 0.026 Uiso 1 1 calc R U . . .
C26 C 0.3557(5) 0.6108(7) 0.7756(3) 0.0216(16) Uani 1 1 d . . . . .
H26 H 0.351142 0.705450 0.790873 0.026 Uiso 1 1 calc R U . . .
C27 C 0.3118(5) 0.5863(7) 0.7327(3) 0.0201(15) Uani 1 1 d . . . . .
H27 H 0.276709 0.663812 0.717897 0.024 Uiso 1 1 calc R U . . .
C28 C 0.3196(4) 0.4456(7) 0.7110(2) 0.0160(13) Uani 1 1 d . . . . .
H28 H 0.291035 0.429169 0.680890 0.019 Uiso 1 1 calc R U . . .
C29 C 0.5822(5) 0.2007(8) 0.7332(2) 0.0201(14) Uani 1 1 d . . . . .
H29A H 0.640034 0.167421 0.749545 0.024 Uiso 1 1 calc R U . . .
H29B H 0.577259 0.310510 0.737136 0.024 Uiso 1 1 calc R U . . .
C30 C 0.5899(5) 0.1643(8) 0.6805(2) 0.0203(14) Uani 1 1 d . . . . .
H30A H 0.639382 0.225938 0.665448 0.024 Uiso 1 1 calc R U . . .
H30B H 0.605833 0.057370 0.675986 0.024 Uiso 1 1 calc R U . . .
C31 C 0.5034(5) 0.2663(8) 0.6133(2) 0.0255(15) Uani 1 1 d . . . . .
H31A H 0.549097 0.349602 0.614035 0.031 Uiso 1 1 calc R U . . .
H31B H 0.441087 0.309493 0.606359 0.031 Uiso 1 1 calc R U . . .
C32 C 0.5296(6) 0.1605(8) 0.5738(3) 0.0312(17) Uani 1 1 d . . . . .
H32A H 0.527845 0.215381 0.543150 0.037 Uiso 1 1 calc R U . . .
H32B H 0.594659 0.126103 0.578963 0.037 Uiso 1 1 calc R U . . .
H2 H 0.309(4) 0.562(8) 0.580(2) 0.037 Uiso 1 1 d D U . . .
H4 H 0.419(6) 0.054(10) 0.580(3) 0.037 Uiso 1 1 d . U . . .


_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
Mn1 N1 2.242(5) . ?
Mn1 N3 2.243(6) . ?
Mn1 O1 2.353(5) . ?
Mn1 N2 2.355(5) . ?
Mn1 Cl1 2.4031(18) . ?
Mn1 Cl2 2.4510(18) . ?
Mn2 N4 2.248(5) . ?
Mn2 N6 2.257(5) . ?
Mn2 N5 2.341(5) . ?
Mn2 O3 2.359(5) . ?
Mn2 Cl3 2.4045(18) . ?
Mn2 Cl4 2.4583(19) . ?
N1 C1 1.349(9) . ?
N1 C5 1.356(8) . ?
N2 C6 1.478(8) . ?
N2 C13 1.482(8) . ?
N2 C7 1.485(8) . ?
N3 C12 1.326(8) . ?
N3 C8 1.353(8) . ?
N4 C17 1.329(9) . ?
N4 C21 1.342(8) . ?
N5 C22 1.470(7) . ?
N5 C23 1.471(8) . ?
N5 C29 1.500(9) . ?
N6 C24 1.327(8) . ?
N6 C28 1.346(8) . ?
O1 C14 1.438(9) . ?
O1 C15 1.440(8) . ?
O2 C16 1.408(9) . ?
O2 H2 0.98(3) . ?
O3 C30 1.431(8) . ?
O3 C31 1.436(7) . ?
O4 C32 1.430(9) . ?
O4 H4 0.80(9) . ?
C1 C2 1.375(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.377(10) . ?
C2 H2A 0.9500 . ?
C3 C4 1.395(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.369(8) . ?
C4 H4A 0.9500 . ?
C5 C6 1.516(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.517(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.397(9) . ?
C9 C10 1.378(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.408(10) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.526(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.510(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.399(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(10) . ?
C19 H19 0.9500 . ?
C20 C21 1.396(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.522(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.525(8) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.396(9) . ?
C25 C26 1.386(9) . ?
C25 H25 0.9500 . ?
C26 C27 1.374(10) . ?
C26 H26 0.9500 . ?
C27 C28 1.400(9) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.516(9) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.503(10) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?

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
N1 Mn1 N3 146.98(19) . . ?
N1 Mn1 O1 82.95(18) . . ?
N3 Mn1 O1 82.63(17) . . ?
N1 Mn1 N2 74.16(18) . . ?
N3 Mn1 N2 73.24(18) . . ?
O1 Mn1 N2 72.84(17) . . ?
N1 Mn1 Cl1 102.44(15) . . ?
N3 Mn1 Cl1 107.29(14) . . ?
O1 Mn1 Cl1 90.75(12) . . ?
N2 Mn1 Cl1 163.47(14) . . ?
N1 Mn1 Cl2 94.29(14) . . ?
N3 Mn1 Cl2 92.29(14) . . ?
O1 Mn1 Cl2 165.40(12) . . ?
N2 Mn1 Cl2 92.60(14) . . ?
Cl1 Mn1 Cl2 103.84(7) . . ?
N4 Mn2 N6 146.38(19) . . ?
N4 Mn2 N5 74.10(18) . . ?
N6 Mn2 N5 72.70(18) . . ?
N4 Mn2 O3 82.68(17) . . ?
N6 Mn2 O3 82.65(18) . . ?
N5 Mn2 O3 72.73(17) . . ?
N4 Mn2 Cl3 102.10(15) . . ?
N6 Mn2 Cl3 108.16(14) . . ?
N5 Mn2 Cl3 163.23(14) . . ?
O3 Mn2 Cl3 90.65(12) . . ?
N4 Mn2 Cl4 94.29(15) . . ?
N6 Mn2 Cl4 92.22(15) . . ?
N5 Mn2 Cl4 92.40(14) . . ?
O3 Mn2 Cl4 165.11(12) . . ?
Cl3 Mn2 Cl4 104.24(7) . . ?
C1 N1 C5 117.9(5) . . ?
C1 N1 Mn1 125.3(4) . . ?
C5 N1 Mn1 116.7(4) . . ?
C6 N2 C13 112.5(5) . . ?
C6 N2 C7 112.5(5) . . ?
C13 N2 C7 110.6(5) . . ?
C6 N2 Mn1 104.8(4) . . ?
C13 N2 Mn1 111.6(4) . . ?
C7 N2 Mn1 104.4(4) . . ?
C12 N3 C8 119.1(6) . . ?
C12 N3 Mn1 125.5(5) . . ?
C8 N3 Mn1 115.4(4) . . ?
C17 N4 C21 119.2(5) . . ?
C17 N4 Mn2 124.9(4) . . ?
C21 N4 Mn2 115.8(4) . . ?
C22 N5 C23 111.7(5) . . ?
C22 N5 C29 113.0(5) . . ?
C23 N5 C29 109.7(5) . . ?
C22 N5 Mn2 105.2(4) . . ?
C23 N5 Mn2 104.8(4) . . ?
C29 N5 Mn2 112.0(3) . . ?
C24 N6 C28 119.3(6) . . ?
C24 N6 Mn2 116.4(4) . . ?
C28 N6 Mn2 124.3(4) . . ?
C14 O1 C15 116.0(5) . . ?
C14 O1 Mn1 113.1(4) . . ?
C15 O1 Mn1 130.4(4) . . ?
C16 O2 H2 102(5) . . ?
C30 O3 C31 115.8(5) . . ?
C30 O3 Mn2 113.0(3) . . ?
C31 O3 Mn2 130.7(4) . . ?
C32 O4 H4 109(6) . . ?
N1 C1 C2 122.8(6) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 119.1(6) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C2 C3 C4 118.5(6) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 119.6(6) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
N1 C5 C4 122.0(6) . . ?
N1 C5 C6 115.5(5) . . ?
C4 C5 C6 122.5(6) . . ?
N2 C6 C5 112.4(5) . . ?
N2 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C8 110.0(5) . . ?
N2 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
N2 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N3 C8 C9 121.9(6) . . ?
N3 C8 C7 117.1(5) . . ?
C9 C8 C7 121.0(6) . . ?
C10 C9 C8 118.9(6) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C11 C10 C9 119.1(6) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 119.3(6) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
N3 C12 C11 121.7(6) . . ?
N3 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
N2 C13 C14 113.7(5) . . ?
N2 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
N2 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
O1 C14 C13 106.5(5) . . ?
O1 C14 H14A 110.4 . . ?
C13 C14 H14A 110.4 . . ?
O1 C14 H14B 110.4 . . ?
C13 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
O1 C15 C16 113.4(6) . . ?
O1 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
O1 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
O2 C16 C15 114.0(6) . . ?
O2 C16 H16A 108.8 . . ?
C15 C16 H16A 108.8 . . ?
O2 C16 H16B 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
N4 C17 C18 122.6(6) . . ?
N4 C17 H17 118.7 . . ?
C18 C17 H17 118.7 . . ?
C19 C18 C17 118.3(6) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
C20 C19 C18 119.1(6) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 119.1(6) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
N4 C21 C20 121.7(6) . . ?
N4 C21 C22 116.4(5) . . ?
C20 C21 C22 121.9(6) . . ?
N5 C22 C21 111.2(5) . . ?
N5 C22 H22A 109.4 . . ?
C21 C22 H22A 109.4 . . ?
N5 C22 H22B 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
N5 C23 C24 110.5(5) . . ?
N5 C23 H23A 109.6 . . ?
C24 C23 H23A 109.6 . . ?
N5 C23 H23B 109.6 . . ?
C24 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
N6 C24 C25 122.4(6) . . ?
N6 C24 C23 116.0(5) . . ?
C25 C24 C23 121.5(5) . . ?
C26 C25 C24 118.4(6) . . ?
C26 C25 H25 120.8 . . ?
C24 C25 H25 120.8 . . ?
C27 C26 C25 119.5(6) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C27 C28 119.0(6) . . ?
C26 C27 H27 120.5 . . ?
C28 C27 H27 120.5 . . ?
N6 C28 C27 121.3(6) . . ?
N6 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
N5 C29 C30 112.9(5) . . ?
N5 C29 H29A 109.0 . . ?
C30 C29 H29A 109.0 . . ?
N5 C29 H29B 109.0 . . ?
C30 C29 H29B 109.0 . . ?
H29A C29 H29B 107.8 . . ?
O3 C30 C29 107.0(6) . . ?
O3 C30 H30A 110.3 . . ?
C29 C30 H30A 110.3 . . ?
O3 C30 H30B 110.3 . . ?
C29 C30 H30B 110.3 . . ?
H30A C30 H30B 108.6 . . ?
O3 C31 C32 113.5(5) . . ?
O3 C31 H31A 108.9 . . ?
C32 C31 H31A 108.9 . . ?
O3 C31 H31B 108.9 . . ?
C32 C31 H31B 108.9 . . ?
H31A C31 H31B 107.7 . . ?
O4 C32 C31 114.0(6) . . ?
O4 C32 H32A 108.8 . . ?
C31 C32 H32A 108.8 . . ?
O4 C32 H32B 108.8 . . ?
C31 C32 H32B 108.8 . . ?
H32A C32 H32B 107.7 . . ?

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
C5 N1 C1 C2 -0.5(9) . . . . ?
Mn1 N1 C1 C2 176.6(5) . . . . ?
N1 C1 C2 C3 0.9(10) . . . . ?
C1 C2 C3 C4 0.0(10) . . . . ?
C2 C3 C4 C5 -1.2(9) . . . . ?
C1 N1 C5 C4 -0.8(9) . . . . ?
Mn1 N1 C5 C4 -178.1(5) . . . . ?
C1 N1 C5 C6 -178.6(5) . . . . ?
Mn1 N1 C5 C6 4.0(7) . . . . ?
C3 C4 C5 N1 1.6(9) . . . . ?
C3 C4 C5 C6 179.3(6) . . . . ?
C13 N2 C6 C5 -77.8(7) . . . . ?
C7 N2 C6 C5 156.5(5) . . . . ?
Mn1 N2 C6 C5 43.7(6) . . . . ?
N1 C5 C6 N2 -34.4(8) . . . . ?
C4 C5 C6 N2 147.8(6) . . . . ?
C6 N2 C7 C8 -159.6(5) . . . . ?
C13 N2 C7 C8 73.6(6) . . . . ?
Mn1 N2 C7 C8 -46.6(5) . . . . ?
C12 N3 C8 C9 -0.3(9) . . . . ?
Mn1 N3 C8 C9 -178.8(5) . . . . ?
C12 N3 C8 C7 -179.6(5) . . . . ?
Mn1 N3 C8 C7 1.9(7) . . . . ?
N2 C7 C8 N3 32.5(8) . . . . ?
N2 C7 C8 C9 -146.9(6) . . . . ?
N3 C8 C9 C10 2.5(10) . . . . ?
C7 C8 C9 C10 -178.2(6) . . . . ?
C8 C9 C10 C11 -3.1(10) . . . . ?
C9 C10 C11 C12 1.7(10) . . . . ?
C8 N3 C12 C11 -1.2(9) . . . . ?
Mn1 N3 C12 C11 177.1(5) . . . . ?
C10 C11 C12 N3 0.5(10) . . . . ?
C6 N2 C13 C14 86.9(6) . . . . ?
C7 N2 C13 C14 -146.4(5) . . . . ?
Mn1 N2 C13 C14 -30.6(6) . . . . ?
C15 O1 C14 C13 140.1(5) . . . . ?
Mn1 O1 C14 C13 -47.0(6) . . . . ?
N2 C13 C14 O1 51.5(7) . . . . ?
C14 O1 C15 C16 75.0(7) . . . . ?
Mn1 O1 C15 C16 -96.4(6) . . . . ?
O1 C15 C16 O2 56.4(8) . . . . ?
C21 N4 C17 C18 0.5(9) . . . . ?
Mn2 N4 C17 C18 177.6(5) . . . . ?
N4 C17 C18 C19 -0.7(10) . . . . ?
C17 C18 C19 C20 0.8(10) . . . . ?
C18 C19 C20 C21 -0.8(10) . . . . ?
C17 N4 C21 C20 -0.5(9) . . . . ?
Mn2 N4 C21 C20 -177.8(5) . . . . ?
C17 N4 C21 C22 -178.8(6) . . . . ?
Mn2 N4 C21 C22 3.8(7) . . . . ?
C19 C20 C21 N4 0.6(9) . . . . ?
C19 C20 C21 C22 178.9(6) . . . . ?
C23 N5 C22 C21 157.6(5) . . . . ?
C29 N5 C22 C21 -78.1(6) . . . . ?
Mn2 N5 C22 C21 44.4(6) . . . . ?
N4 C21 C22 N5 -34.7(8) . . . . ?
C20 C21 C22 N5 147.0(6) . . . . ?
C22 N5 C23 C24 -160.1(5) . . . . ?
C29 N5 C23 C24 73.7(6) . . . . ?
Mn2 N5 C23 C24 -46.7(5) . . . . ?
C28 N6 C24 C25 3.4(9) . . . . ?
Mn2 N6 C24 C25 -175.5(5) . . . . ?
C28 N6 C24 C23 -179.9(5) . . . . ?
Mn2 N6 C24 C23 1.2(7) . . . . ?
N5 C23 C24 N6 32.8(8) . . . . ?
N5 C23 C24 C25 -150.5(6) . . . . ?
N6 C24 C25 C26 -1.3(10) . . . . ?
C23 C24 C25 C26 -177.8(6) . . . . ?
C24 C25 C26 C27 -0.5(10) . . . . ?
C25 C26 C27 C28 0.1(10) . . . . ?
C24 N6 C28 C27 -3.7(9) . . . . ?
Mn2 N6 C28 C27 175.1(5) . . . . ?
C26 C27 C28 N6 2.0(9) . . . . ?
C22 N5 C29 C30 87.9(6) . . . . ?
C23 N5 C29 C30 -146.7(5) . . . . ?
Mn2 N5 C29 C30 -30.8(6) . . . . ?
C31 O3 C30 C29 140.1(5) . . . . ?
Mn2 O3 C30 C29 -47.3(6) . . . . ?
N5 C29 C30 O3 51.6(7) . . . . ?
C30 O3 C31 C32 74.6(8) . . . . ?
Mn2 O3 C31 C32 -96.5(6) . . . . ?
O3 C31 C32 O4 56.7(9) . . . . ?

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
O2 H2 Cl1 0.98(3) 2.28(3) 3.246(6) 168(7) .
O4 H4 Cl3 0.80(9) 2.48(9) 3.247(6) 162(8) .

_refine_diff_density_max         0.941
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.088



