# 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 2019

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1909685'
loop_
_audit_author_name
_audit_author_address
'Yu-Hsin Liu'
;NTNU University
Taiwan
;
_audit_update_record             
;
2019-04-12 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H6 Cu2 Fe3 N2 O9 Se'
_chemical_formula_sum            'C13 H6 Cu2 Fe3 N2 O9 Se'
_chemical_formula_weight         707.79

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.8011(9)
_cell_length_b                   10.7748(10)
_cell_length_c                   12.1648(12)
_cell_angle_alpha                85.346(2)
_cell_angle_beta                 79.733(2)
_cell_angle_gamma                68.143(2)
_cell_volume                     1053.38(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4949
_cell_measurement_theta_min      2.523
_cell_measurement_theta_max      24.997

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.231
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    5.777
_shelx_estimated_absorpt_T_min   0.137
_shelx_estimated_absorpt_T_max   0.544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1373
_exptl_absorpt_correction_T_max  0.5440
_exptl_absorpt_process_details   'SADABS, 2003'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8505
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.701
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3656
_reflns_number_gt                3211
_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 APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0199P)²+0.2680P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3656
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0215
_refine_ls_wR_factor_ref         0.0476
_refine_ls_wR_factor_gt          0.0460
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0705(4) 0.8298(3) 0.1973(2) 0.0320(7) Uani 1 1 d . . . . .
C2 C 0.1474(3) 0.9472(3) 0.1047(2) 0.0266(6) Uani 1 1 d . . . . .
C3 C 0.2172(4) 0.6737(3) 0.1148(2) 0.0331(7) Uani 1 1 d . . . . .
C4 C 0.5416(4) 0.6846(3) 0.3255(3) 0.0389(8) Uani 1 1 d . . . . .
C5 C 0.4080(3) 0.9533(3) 0.2757(2) 0.0328(7) Uani 1 1 d . . . . .
C6 C 0.3642(3) 0.8508(3) 0.4798(2) 0.0336(7) Uani 1 1 d . . . . .
C7 C 0.1321(3) 0.7069(3) 0.5503(2) 0.0284(7) Uani 1 1 d . . . . .
C8 C -0.1250(4) 0.7760(3) 0.4481(2) 0.0368(7) Uani 1 1 d . . . . .
C9 C 0.1293(4) 0.5626(3) 0.3840(2) 0.0403(8) Uani 1 1 d . . . . .
C10 C 0.5899(4) 0.3262(3) 0.2065(2) 0.0273(6) Uani 1 1 d . . . . .
C11 C 0.7110(3) 0.1955(3) 0.1720(2) 0.0328(7) Uani 1 1 d . . . . .
H11A H 0.6536 0.1384 0.1557 0.049 Uiso 1 1 calc R U . . .
H11B H 0.7752 0.1545 0.2322 0.049 Uiso 1 1 calc R U . . .
H11C H 0.7859 0.2057 0.1049 0.049 Uiso 1 1 calc R U . . .
C12 C 0.7214(4) 0.7138(3) -0.0515(3) 0.0409(8) Uani 1 1 d . . . . .
C13 C 0.8660(5) 0.6780(4) -0.1398(3) 0.0703(13) Uani 1 1 d . . . . .
H13A H 0.9611 0.6105 -0.1112 0.105 Uiso 1 1 calc R U . . .
H13B H 0.8921 0.7578 -0.1643 0.105 Uiso 1 1 calc R U . . .
H13C H 0.8419 0.6418 -0.2031 0.105 Uiso 1 1 calc R U . . .
N1 N 0.4956(3) 0.4281(2) 0.2328(2) 0.0343(6) Uani 1 1 d . . . . .
N2 N 0.6109(3) 0.7412(3) 0.0162(2) 0.0398(7) Uani 1 1 d . . . . .
O1 O -0.2020(3) 0.8390(3) 0.19109(19) 0.0543(6) Uani 1 1 d . . . . .
O2 O 0.1433(3) 1.0368(2) 0.04549(17) 0.0428(5) Uani 1 1 d . . . . .
O3 O 0.2493(3) 0.5913(2) 0.04981(18) 0.0542(7) Uani 1 1 d . . . . .
O4 O 0.6750(3) 0.6085(2) 0.3224(2) 0.0663(8) Uani 1 1 d . . . . .
O5 O 0.4382(3) 1.0443(2) 0.2399(2) 0.0542(6) Uani 1 1 d . . . . .
O6 O 0.3778(3) 0.8712(3) 0.56725(17) 0.0548(7) Uani 1 1 d . . . . .
O7 O 0.1493(3) 0.6900(2) 0.64205(16) 0.0422(5) Uani 1 1 d . . . . .
O8 O -0.2642(3) 0.8056(3) 0.4756(2) 0.0657(7) Uani 1 1 d . . . . .
O9 O 0.1278(3) 0.4575(2) 0.3762(2) 0.0688(8) Uani 1 1 d . . . . .
Fe1 Fe 0.13608(4) 0.81642(4) 0.20130(3) 0.02090(10) Uani 1 1 d . . . . .
Fe2 Fe 0.34577(4) 0.82174(4) 0.34157(3) 0.02182(10) Uani 1 1 d . . . . .
Fe3 Fe 0.09336(5) 0.73218(4) 0.41002(3) 0.02258(10) Uani 1 1 d . . . . .
Cu1 Cu 0.34676(4) 0.60452(3) 0.27942(3) 0.03026(10) Uani 1 1 d . . . . .
Cu2 Cu 0.43391(4) 0.77769(4) 0.13755(3) 0.03518(10) Uani 1 1 d . . . . .
Se1 Se 0.06667(3) 0.94839(3) 0.35824(2) 0.02295(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.140(3) . ?
C1 Fe1 1.779(3) . ?
C2 O2 1.150(3) . ?
C2 Fe1 1.780(3) . ?
C3 O3 1.158(3) . ?
C3 Fe1 1.777(3) . ?
C3 Cu1 2.410(3) . ?
C4 O4 1.151(3) . ?
C4 Fe2 1.795(3) . ?
C4 Cu1 2.349(3) . ?
C5 O5 1.142(3) . ?
C5 Fe2 1.786(3) . ?
C6 O6 1.139(3) . ?
C6 Fe2 1.781(3) . ?
C7 O7 1.144(3) . ?
C7 Fe3 1.779(3) . ?
C8 O8 1.138(3) . ?
C8 Fe3 1.781(3) . ?
C9 O9 1.149(3) . ?
C9 Fe3 1.779(3) . ?
C9 Cu1 2.274(3) . ?
C10 N1 1.131(3) . ?
C10 C11 1.454(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N2 1.119(3) . ?
C12 C13 1.462(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 Cu1 1.926(2) . ?
N2 Cu2 1.891(2) . ?
Fe1 Se1 2.3276(4) . ?
Fe1 Cu2 2.4819(6) . ?
Fe1 Cu1 2.5842(5) . ?
Fe1 Fe3 2.6366(6) . ?
Fe1 Fe2 2.7456(5) . ?
Fe2 Se1 2.3041(5) . ?
Fe2 Cu2 2.4934(5) . ?
Fe2 Cu1 2.5139(5) . ?
Fe2 Fe3 2.7141(6) . ?
Fe3 Se1 2.2992(5) . ?
Fe3 Cu1 2.4894(5) . ?
Cu1 Cu2 2.6682(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 C1 Fe1 177.8(3) . . ?
O2 C2 Fe1 175.1(3) . . ?
O3 C3 Fe1 169.3(3) . . ?
O3 C3 Cu1 115.7(2) . . ?
Fe1 C3 Cu1 74.52(10) . . ?
O4 C4 Fe2 170.1(3) . . ?
O4 C4 Cu1 116.5(2) . . ?
Fe2 C4 Cu1 73.31(10) . . ?
O5 C5 Fe2 174.4(3) . . ?
O6 C6 Fe2 178.5(3) . . ?
O7 C7 Fe3 176.5(3) . . ?
O8 C8 Fe3 177.8(3) . . ?
O9 C9 Fe3 169.3(3) . . ?
O9 C9 Cu1 115.9(2) . . ?
Fe3 C9 Cu1 74.68(11) . . ?
N1 C10 C11 179.7(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 179.9(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 N1 Cu1 176.3(2) . . ?
C12 N2 Cu2 175.7(3) . . ?
C3 Fe1 C1 91.09(13) . . ?
C3 Fe1 C2 102.47(12) . . ?
C1 Fe1 C2 99.26(13) . . ?
C3 Fe1 Se1 160.77(9) . . ?
C1 Fe1 Se1 95.12(9) . . ?
C2 Fe1 Se1 94.48(8) . . ?
C3 Fe1 Cu2 73.41(10) . . ?
C1 Fe1 Cu2 159.83(9) . . ?
C2 Fe1 Cu2 72.44(9) . . ?
Se1 Fe1 Cu2 103.722(17) . . ?
C3 Fe1 Cu1 63.97(9) . . ?
C1 Fe1 Cu1 121.54(10) . . ?
C2 Fe1 Cu1 135.93(9) . . ?
Se1 Fe1 Cu1 97.458(17) . . ?
Cu2 Fe1 Cu1 63.526(15) . . ?
C3 Fe1 Fe3 107.60(9) . . ?
C1 Fe1 Fe3 87.10(9) . . ?
C2 Fe1 Fe3 149.14(8) . . ?
Se1 Fe1 Fe3 54.754(15) . . ?
Cu2 Fe1 Fe3 109.587(18) . . ?
Cu1 Fe1 Fe3 56.946(14) . . ?
C3 Fe1 Fe2 113.61(10) . . ?
C1 Fe1 Fe2 143.37(9) . . ?
C2 Fe1 Fe2 101.04(9) . . ?
Se1 Fe1 Fe2 53.251(13) . . ?
Cu2 Fe1 Fe2 56.708(15) . . ?
Cu1 Fe1 Fe2 56.187(14) . . ?
Fe3 Fe1 Fe2 60.526(15) . . ?
C6 Fe2 C5 96.34(13) . . ?
C6 Fe2 C4 91.74(14) . . ?
C5 Fe2 C4 100.40(14) . . ?
C6 Fe2 Se1 95.22(9) . . ?
C5 Fe2 Se1 93.99(9) . . ?
C4 Fe2 Se1 163.23(10) . . ?
C6 Fe2 Cu2 157.43(9) . . ?
C5 Fe2 Cu2 71.04(9) . . ?
C4 Fe2 Cu2 73.00(10) . . ?
Se1 Fe2 Cu2 104.066(18) . . ?
C6 Fe2 Cu1 123.97(11) . . ?
C5 Fe2 Cu1 135.27(9) . . ?
C4 Fe2 Cu1 63.53(9) . . ?
Se1 Fe2 Cu1 100.088(17) . . ?
Cu2 Fe2 Cu1 64.398(15) . . ?
C6 Fe2 Fe3 93.95(9) . . ?
C5 Fe2 Fe3 146.98(9) . . ?
C4 Fe2 Fe3 110.58(10) . . ?
Se1 Fe2 Fe3 53.788(15) . . ?
Cu2 Fe2 Fe3 106.817(17) . . ?
Cu1 Fe2 Fe3 56.716(14) . . ?
C6 Fe2 Fe1 146.11(9) . . ?
C5 Fe2 Fe1 99.45(9) . . ?
C4 Fe2 Fe1 114.41(10) . . ?
Se1 Fe2 Fe1 54.043(13) . . ?
Cu2 Fe2 Fe1 56.307(14) . . ?
Cu1 Fe2 Fe1 58.660(14) . . ?
Fe3 Fe2 Fe1 57.750(14) . . ?
C7 Fe3 C9 96.67(14) . . ?
C7 Fe3 C8 94.33(13) . . ?
C9 Fe3 C8 93.61(14) . . ?
C7 Fe3 Se1 107.69(9) . . ?
C9 Fe3 Se1 154.28(10) . . ?
C8 Fe3 Se1 92.65(10) . . ?
C7 Fe3 Cu1 110.48(9) . . ?
C9 Fe3 Cu1 61.74(9) . . ?
C8 Fe3 Cu1 146.08(9) . . ?
Se1 Fe3 Cu1 100.948(18) . . ?
C7 Fe3 Fe1 154.46(9) . . ?
C9 Fe3 Fe1 98.53(10) . . ?
C8 Fe3 Fe1 105.02(10) . . ?
Se1 Fe3 Fe1 55.770(13) . . ?
Cu1 Fe3 Fe1 60.466(15) . . ?
C7 Fe3 Fe2 92.98(9) . . ?
C9 Fe3 Fe2 118.02(10) . . ?
C8 Fe3 Fe2 146.39(10) . . ?
Se1 Fe3 Fe2 53.955(14) . . ?
Cu1 Fe3 Fe2 57.584(15) . . ?
Fe1 Fe3 Fe2 61.725(14) . . ?
N1 Cu1 C9 102.15(11) . . ?
N1 Cu1 C4 98.54(11) . . ?
C9 Cu1 C4 132.31(11) . . ?
N1 Cu1 C3 98.48(10) . . ?
C9 Cu1 C3 94.88(11) . . ?
C4 Cu1 C3 123.89(11) . . ?
N1 Cu1 Fe3 144.45(8) . . ?
C9 Cu1 Fe3 43.58(8) . . ?
C4 Cu1 Fe3 101.33(8) . . ?
C3 Cu1 Fe3 94.49(7) . . ?
N1 Cu1 Fe2 141.50(7) . . ?
C9 Cu1 Fe2 108.26(8) . . ?
C4 Cu1 Fe2 43.16(8) . . ?
C3 Cu1 Fe2 101.81(7) . . ?
Fe3 Cu1 Fe2 65.700(15) . . ?
N1 Cu1 Fe1 139.76(7) . . ?
C9 Cu1 Fe1 88.36(9) . . ?
C4 Cu1 Fe1 102.55(8) . . ?
C3 Cu1 Fe1 41.51(7) . . ?
Fe3 Cu1 Fe1 62.588(15) . . ?
Fe2 Cu1 Fe1 65.154(15) . . ?
N1 Cu1 Cu2 106.94(8) . . ?
C9 Cu1 Cu2 144.62(9) . . ?
C4 Cu1 Cu2 62.36(8) . . ?
C3 Cu1 Cu2 61.55(7) . . ?
Fe3 Cu1 Cu2 108.350(17) . . ?
Fe2 Cu1 Cu2 57.430(14) . . ?
Fe1 Cu1 Cu2 56.370(15) . . ?
N2 Cu2 Fe1 146.97(8) . . ?
N2 Cu2 Fe2 146.04(8) . . ?
Fe1 Cu2 Fe2 66.985(14) . . ?
N2 Cu2 Cu1 128.32(8) . . ?
Fe1 Cu2 Cu1 60.104(14) . . ?
Fe2 Cu2 Cu1 58.172(14) . . ?
Fe3 Se1 Fe2 72.257(16) . . ?
Fe3 Se1 Fe1 69.476(16) . . ?
Fe2 Se1 Fe1 72.707(15) . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1909691'
loop_
_audit_author_name
_audit_author_address
'Yu-Hsin Liu'
;NTNU University
Taiwan
;
_audit_update_record             
;
2019-04-12 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 Cu2 Fe3 N4 O9 Se'
_chemical_formula_sum            'C19 H16 Cu2 Fe3 N4 O9 Se'
_chemical_formula_weight         817.95

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.8056(3)
_cell_length_b                   13.7351(3)
_cell_length_c                   14.3112(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.7930(10)
_cell_angle_gamma                90
_cell_volume                     2656.43(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9321
_cell_measurement_theta_min      2.037
_cell_measurement_theta_max      25.028

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.045
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    4.599
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3049
_exptl_absorpt_correction_T_max  0.5059
_exptl_absorpt_process_details   'SADABS, 2003'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            10369
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_av_R_equivalents  0.1211
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.076
_diffrn_reflns_theta_max         25.080
_diffrn_reflns_theta_full        25.080
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4686
_reflns_number_gt                4008
_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       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0758P)²+1.4400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4686
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1666
_refine_ls_wR_factor_gt          0.1425
_refine_ls_goodness_of_fit_ref   1.359
_refine_ls_restrained_S_all      1.359
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.85501(5) 0.58332(4) 0.20510(4) 0.0379(2) Uani 1 1 d . . . . .
Cu1 Cu 0.98432(6) 0.83918(5) 0.23874(6) 0.0406(2) Uani 1 1 d . . . . .
Cu2 Cu 0.95042(7) 0.67606(7) 0.11096(6) 0.0516(3) Uani 1 1 d . . . . .
Fe1 Fe 0.82363(6) 0.74929(6) 0.22184(6) 0.0316(2) Uani 1 1 d . . . . .
Fe2 Fe 0.99799(6) 0.66236(6) 0.28980(6) 0.0308(2) Uani 1 1 d . . . . .
Fe3 Fe 0.84149(6) 0.61953(6) 0.35927(6) 0.0348(2) Uani 1 1 d . . . . .
O1 O 0.6076(4) 0.7414(5) 0.1808(4) 0.0715(18) Uani 1 1 d . . . . .
O2 O 0.8277(4) 0.8951(4) 0.3717(4) 0.0595(14) Uani 1 1 d . . . . .
O3 O 0.8185(5) 0.8713(4) 0.0527(4) 0.0652(15) Uani 1 1 d . . . . .
O4 O 1.0528(4) 0.7837(4) 0.4599(3) 0.0559(13) Uani 1 1 d . . . . .
O5 O 1.1652(3) 0.7204(5) 0.2051(4) 0.0581(13) Uani 1 1 d . . . . .
O6 O 1.1180(5) 0.4951(4) 0.3665(4) 0.0665(15) Uani 1 1 d . . . . .
O7 O 0.6316(4) 0.5872(6) 0.3496(5) 0.084(2) Uani 1 1 d . . . . .
O8 O 0.9109(5) 0.4300(4) 0.4384(4) 0.0622(14) Uani 1 1 d . . . . .
O9 O 0.8620(5) 0.7265(5) 0.5391(4) 0.0708(16) Uani 1 1 d . . . . .
N1 N 1.0715(4) 1.0317(4) 0.2961(4) 0.0437(13) Uani 1 1 d . . . . .
N2 N 1.1022(4) 0.9878(4) 0.1632(4) 0.0464(13) Uani 1 1 d . . . . .
N3 N 1.0188(5) 0.6518(5) -0.0726(5) 0.0576(16) Uani 1 1 d . . . . .
N4 N 0.8634(5) 0.6485(5) -0.0909(4) 0.0559(16) Uani 1 1 d . . . . .
C1 C 0.6939(5) 0.7435(5) 0.1965(5) 0.0451(16) Uani 1 1 d . . . . .
C2 C 0.8304(5) 0.8383(5) 0.3136(5) 0.0408(15) Uani 1 1 d . . . . .
C3 C 0.8275(5) 0.8206(5) 0.1187(5) 0.0444(16) Uani 1 1 d . . . . .
C4 C 1.0270(5) 0.7363(5) 0.3946(4) 0.0389(14) Uani 1 1 d . . . . .
C5 C 1.0906(4) 0.6999(5) 0.2289(5) 0.0409(14) Uani 1 1 d . . . . .
C6 C 1.0699(5) 0.5589(5) 0.3371(4) 0.0421(15) Uani 1 1 d . . . . .
C7 C 0.7146(6) 0.5997(6) 0.3527(5) 0.0519(18) Uani 1 1 d . . . . .
C8 C 0.8839(5) 0.5043(5) 0.4091(4) 0.0446(15) Uani 1 1 d . . . . .
C9 C 0.8570(5) 0.6879(5) 0.4687(5) 0.0463(16) Uani 1 1 d . . . . .
C10 C 1.0569(4) 0.9584(4) 0.2340(4) 0.0369(13) Uani 1 1 d . . . . .
C11 C 1.0341(7) 1.0353(6) 0.3843(5) 0.061(2) Uani 1 1 d . . . . .
H11A H 1.0541 1.0953 0.4170 0.092 Uiso 1 1 calc R U . . .
H11B H 0.9631 1.0315 0.3695 0.092 Uiso 1 1 calc R U . . .
H11C H 1.0603 0.9815 0.4244 0.092 Uiso 1 1 calc R U . . .
C12 C 1.1243(7) 1.1056(6) 0.2659(7) 0.068(2) Uani 1 1 d . . . . .
H12 H 1.1428 1.1639 0.2975 0.081 Uiso 1 1 calc R U . . .
C13 C 1.1436(7) 1.0783(7) 0.1837(7) 0.073(3) Uani 1 1 d . . . . .
H13 H 1.1788 1.1136 0.1462 0.088 Uiso 1 1 calc R U . . .
C14 C 1.1095(7) 0.9309(7) 0.0797(5) 0.065(2) Uani 1 1 d . . . . .
H14A H 1.1449 0.9674 0.0402 0.097 Uiso 1 1 calc R U . . .
H14B H 1.1442 0.8714 0.0992 0.097 Uiso 1 1 calc R U . . .
H14C H 1.0443 0.9163 0.0442 0.097 Uiso 1 1 calc R U . . .
C15 C 0.9451(5) 0.6590(5) -0.0236(5) 0.0466(16) Uani 1 1 d . . . . .
C16 C 1.1226(7) 0.6559(10) -0.0308(8) 0.094(4) Uani 1 1 d . . . . .
H16A H 1.1602 0.6491 -0.0800 0.141 Uiso 1 1 calc R U . . .
H16B H 1.1378 0.7172 0.0009 0.141 Uiso 1 1 calc R U . . .
H16C H 1.1393 0.6040 0.0145 0.141 Uiso 1 1 calc R U . . .
C17 C 0.9792(8) 0.6368(7) -0.1684(6) 0.073(3) Uani 1 1 d . . . . .
H17 H 1.0147 0.6299 -0.2167 0.087 Uiso 1 1 calc R U . . .
C18 C 0.8811(8) 0.6341(8) -0.1790(6) 0.075(3) Uani 1 1 d . . . . .
H18 H 0.8347 0.6242 -0.2353 0.090 Uiso 1 1 calc R U . . .
C19 C 0.7622(7) 0.6485(11) -0.0733(7) 0.098(4) Uani 1 1 d . . . . .
H19A H 0.7159 0.6398 -0.1326 0.147 Uiso 1 1 calc R U . . .
H19B H 0.7552 0.5963 -0.0306 0.147 Uiso 1 1 calc R U . . .
H19C H 0.7496 0.7094 -0.0451 0.147 Uiso 1 1 calc R 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
Se1 Fe3 2.3062(10) . ?
Se1 Fe1 2.3417(10) . ?
Se1 Fe2 2.3593(10) . ?
Se1 Cu2 2.4285(10) . ?
Cu1 C10 1.928(6) . ?
Cu1 C5 2.432(7) . ?
Cu1 C3 2.487(7) . ?
Cu1 Fe1 2.5071(11) . ?
Cu1 Fe2 2.5322(11) . ?
Cu1 Cu2 2.8693(12) . ?
Cu2 C15 1.926(7) . ?
Cu2 C5 2.317(6) . ?
Cu2 Fe2 2.5159(11) . ?
Cu2 Fe1 2.7800(12) . ?
Fe1 C1 1.755(7) . ?
Fe1 C3 1.781(7) . ?
Fe1 C2 1.782(7) . ?
Fe1 Fe3 2.6282(11) . ?
Fe1 Fe2 2.6849(11) . ?
Fe2 C5 1.764(6) . ?
Fe2 C6 1.785(7) . ?
Fe2 C4 1.787(6) . ?
Fe2 Fe3 2.6231(11) . ?
Fe3 C7 1.756(7) . ?
Fe3 C8 1.785(7) . ?
Fe3 C9 1.802(7) . ?
O1 C1 1.167(9) . ?
O2 C2 1.146(8) . ?
O3 C3 1.159(8) . ?
O4 C4 1.135(8) . ?
O5 C5 1.184(8) . ?
O6 C6 1.128(8) . ?
O7 C7 1.151(9) . ?
O8 C8 1.137(8) . ?
O9 C9 1.127(9) . ?
N1 C10 1.331(8) . ?
N1 C12 1.370(9) . ?
N1 C11 1.459(9) . ?
N2 C10 1.356(8) . ?
N2 C13 1.374(10) . ?
N2 C14 1.449(9) . ?
N3 C15 1.352(9) . ?
N3 C17 1.383(11) . ?
N3 C16 1.437(12) . ?
N4 C15 1.333(10) . ?
N4 C18 1.348(10) . ?
N4 C19 1.469(11) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.313(12) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.332(14) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
Fe3 Se1 Fe1 68.86(3) . . ?
Fe3 Se1 Fe2 68.41(3) . . ?
Fe1 Se1 Fe2 69.66(3) . . ?
Fe3 Se1 Cu2 125.22(4) . . ?
Fe1 Se1 Cu2 71.27(3) . . ?
Fe2 Se1 Cu2 63.38(3) . . ?
C10 Cu1 C5 110.0(2) . . ?
C10 Cu1 C3 116.6(2) . . ?
C5 Cu1 C3 109.2(2) . . ?
C10 Cu1 Fe1 150.56(19) . . ?
C5 Cu1 Fe1 98.01(16) . . ?
C3 Cu1 Fe1 41.79(15) . . ?
C10 Cu1 Fe2 144.70(19) . . ?
C5 Cu1 Fe2 41.58(16) . . ?
C3 Cu1 Fe2 95.96(16) . . ?
Fe1 Cu1 Fe2 64.39(3) . . ?
C10 Cu1 Cu2 131.21(19) . . ?
C5 Cu1 Cu2 51.01(16) . . ?
C3 Cu1 Cu2 58.25(16) . . ?
Fe1 Cu1 Cu2 61.84(3) . . ?
Fe2 Cu1 Cu2 55.09(3) . . ?
C15 Cu2 C5 127.0(3) . . ?
C15 Cu2 Se1 125.2(2) . . ?
C5 Cu2 Se1 97.86(16) . . ?
C15 Cu2 Fe2 163.0(2) . . ?
C5 Cu2 Fe2 42.58(16) . . ?
Se1 Cu2 Fe2 56.97(3) . . ?
C15 Cu2 Fe1 135.6(2) . . ?
C5 Cu2 Fe1 93.57(16) . . ?
Se1 Cu2 Fe1 52.91(3) . . ?
Fe2 Cu2 Fe1 60.68(3) . . ?
C15 Cu2 Cu1 134.4(2) . . ?
C5 Cu2 Cu1 54.67(17) . . ?
Se1 Cu2 Cu1 95.30(3) . . ?
Fe2 Cu2 Cu1 55.63(3) . . ?
Fe1 Cu2 Cu1 52.66(3) . . ?
C1 Fe1 C3 93.2(3) . . ?
C1 Fe1 C2 94.7(3) . . ?
C3 Fe1 C2 103.2(3) . . ?
C1 Fe1 Se1 97.9(2) . . ?
C3 Fe1 Se1 114.4(2) . . ?
C2 Fe1 Se1 139.5(2) . . ?
C1 Fe1 Cu1 152.6(2) . . ?
C3 Fe1 Cu1 68.5(2) . . ?
C2 Fe1 Cu1 71.3(2) . . ?
Se1 Fe1 Cu1 108.10(4) . . ?
C1 Fe1 Fe3 93.4(2) . . ?
C3 Fe1 Fe3 168.2(2) . . ?
C2 Fe1 Fe3 86.0(2) . . ?
Se1 Fe1 Fe3 54.93(3) . . ?
Cu1 Fe1 Fe3 108.42(4) . . ?
C1 Fe1 Fe2 148.9(2) . . ?
C3 Fe1 Fe2 111.6(2) . . ?
C2 Fe1 Fe2 97.5(2) . . ?
Se1 Fe1 Fe2 55.48(3) . . ?
Cu1 Fe1 Fe2 58.26(3) . . ?
Fe3 Fe1 Fe2 59.16(3) . . ?
C1 Fe1 Cu2 126.9(2) . . ?
C3 Fe1 Cu2 66.2(2) . . ?
C2 Fe1 Cu2 136.4(2) . . ?
Se1 Fe1 Cu2 55.82(3) . . ?
Cu1 Fe1 Cu2 65.50(3) . . ?
Fe3 Fe1 Cu2 102.01(4) . . ?
Fe2 Fe1 Cu2 54.79(3) . . ?
C5 Fe2 C6 91.0(3) . . ?
C5 Fe2 C4 100.8(3) . . ?
C6 Fe2 C4 97.0(3) . . ?
C5 Fe2 Se1 119.7(2) . . ?
C6 Fe2 Se1 99.8(2) . . ?
C4 Fe2 Se1 135.5(2) . . ?
C5 Fe2 Cu2 62.7(2) . . ?
C6 Fe2 Cu2 117.0(2) . . ?
C4 Fe2 Cu2 141.1(2) . . ?
Se1 Fe2 Cu2 59.65(3) . . ?
C5 Fe2 Cu1 66.2(2) . . ?
C6 Fe2 Cu1 151.1(2) . . ?
C4 Fe2 Cu1 71.8(2) . . ?
Se1 Fe2 Cu1 106.73(4) . . ?
Cu2 Fe2 Cu1 69.28(4) . . ?
C5 Fe2 Fe3 171.3(2) . . ?
C6 Fe2 Fe3 96.6(2) . . ?
C4 Fe2 Fe3 82.5(2) . . ?
Se1 Fe2 Fe3 54.84(3) . . ?
Cu2 Fe2 Fe3 109.78(4) . . ?
Cu1 Fe2 Fe3 107.81(4) . . ?
C5 Fe2 Fe1 112.2(2) . . ?
C6 Fe2 Fe1 151.5(2) . . ?
C4 Fe2 Fe1 94.7(2) . . ?
Se1 Fe2 Fe1 54.86(3) . . ?
Cu2 Fe2 Fe1 64.53(3) . . ?
Cu1 Fe2 Fe1 57.35(3) . . ?
Fe3 Fe2 Fe1 59.35(3) . . ?
C7 Fe3 C8 97.2(3) . . ?
C7 Fe3 C9 93.9(3) . . ?
C8 Fe3 C9 98.3(3) . . ?
C7 Fe3 Se1 100.9(2) . . ?
C8 Fe3 Se1 96.2(2) . . ?
C9 Fe3 Se1 157.8(2) . . ?
C7 Fe3 Fe2 154.7(2) . . ?
C8 Fe3 Fe2 97.0(2) . . ?
C9 Fe3 Fe2 104.6(2) . . ?
Se1 Fe3 Fe2 56.75(3) . . ?
C7 Fe3 Fe1 97.2(2) . . ?
C8 Fe3 Fe1 150.9(2) . . ?
C9 Fe3 Fe1 105.9(2) . . ?
Se1 Fe3 Fe1 56.21(3) . . ?
Fe2 Fe3 Fe1 61.50(3) . . ?
C10 N1 C12 111.6(6) . . ?
C10 N1 C11 124.8(6) . . ?
C12 N1 C11 123.6(6) . . ?
C10 N2 C13 110.3(6) . . ?
C10 N2 C14 125.2(6) . . ?
C13 N2 C14 124.5(6) . . ?
C15 N3 C17 109.8(7) . . ?
C15 N3 C16 125.0(7) . . ?
C17 N3 C16 125.2(7) . . ?
C15 N4 C18 113.8(7) . . ?
C15 N4 C19 124.7(6) . . ?
C18 N4 C19 121.4(7) . . ?
O1 C1 Fe1 178.6(8) . . ?
O2 C2 Fe1 175.2(6) . . ?
O3 C3 Fe1 171.4(6) . . ?
O3 C3 Cu1 115.7(6) . . ?
Fe1 C3 Cu1 69.7(2) . . ?
O4 C4 Fe2 174.6(6) . . ?
O5 C5 Fe2 166.6(6) . . ?
O5 C5 Cu2 118.0(5) . . ?
Fe2 C5 Cu2 74.8(2) . . ?
O5 C5 Cu1 113.7(5) . . ?
Fe2 C5 Cu1 72.3(2) . . ?
Cu2 C5 Cu1 74.31(18) . . ?
O6 C6 Fe2 177.7(7) . . ?
O7 C7 Fe3 179.0(8) . . ?
O8 C8 Fe3 178.1(6) . . ?
O9 C9 Fe3 175.2(6) . . ?
N1 C10 N2 104.1(5) . . ?
N1 C10 Cu1 128.9(4) . . ?
N2 C10 Cu1 127.0(5) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N1 106.8(7) . . ?
C13 C12 H12 126.6 . . ?
N1 C12 H12 126.6 . . ?
C12 C13 N2 107.3(7) . . ?
C12 C13 H13 126.4 . . ?
N2 C13 H13 126.4 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 N3 103.4(6) . . ?
N4 C15 Cu2 126.1(5) . . ?
N3 C15 Cu2 130.4(6) . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N3 107.7(7) . . ?
C18 C17 H17 126.1 . . ?
N3 C17 H17 126.1 . . ?
C17 C18 N4 105.3(8) . . ?
C17 C18 H18 127.4 . . ?
N4 C18 H18 127.4 . . ?
N4 C19 H19A 109.5 . . ?
N4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         1.044
_refine_diff_density_min         -2.702
_refine_diff_density_rms         0.522

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1909692'
loop_
_audit_author_name
_audit_author_address
'Yu-Hsin Liu'
;NTNU University
Taiwan
;
_audit_update_record             
;
2019-04-12 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H20 Cu2 Fe3 N4 O9 Se'
_chemical_formula_sum            'C27 H20 Cu2 Fe3 N4 O9 Se'
_chemical_formula_weight         918.06

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.211(2)
_cell_length_b                   18.962(4)
_cell_length_c                   16.852(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.308(6)
_cell_angle_gamma                90
_cell_volume                     3147.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1598
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      21.56

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.893
_shelx_estimated_absorpt_T_min   0.575
_shelx_estimated_absorpt_T_max   0.697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5747
_exptl_absorpt_correction_T_max  0.6968
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16893
_diffrn_reflns_av_unetI/netI     0.0980
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.116
_diffrn_reflns_theta_max         25.013
_diffrn_reflns_theta_full        25.013
_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             5535
_reflns_number_gt                3334
_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 APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0396P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5535
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_restrained_S_all      0.907
_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
C1 C 0.5292(7) 0.2104(3) 0.0551(4) 0.0448(17) Uani 1 1 d . . . . .
C2 C 0.6555(6) 0.3257(4) 0.1206(4) 0.0379(16) Uani 1 1 d . . . . .
C3 C 0.7680(7) 0.2374(3) 0.0332(4) 0.0449(17) Uani 1 1 d . . . . .
C4 C 0.8331(6) 0.3092(4) 0.3032(4) 0.0403(17) Uani 1 1 d . . . . .
C5 C 1.0342(7) 0.2246(3) 0.2676(4) 0.0449(17) Uani 1 1 d . . . . .
C6 C 0.9066(6) 0.1806(3) 0.3662(4) 0.0416(17) Uani 1 1 d . . . . .
C7 C 0.6148(6) 0.1898(3) 0.3502(4) 0.0400(16) Uani 1 1 d . . . . .
C8 C 0.4377(7) 0.1702(3) 0.2055(4) 0.0418(17) Uani 1 1 d . . . . .
C9 C 0.5341(6) 0.2994(4) 0.2527(4) 0.0423(17) Uani 1 1 d . . . . .
C10 C 1.0212(6) 0.3802(3) 0.1393(3) 0.0299(14) Uani 1 1 d . . . . .
C11 C 0.9038(6) 0.4899(3) 0.1679(4) 0.0530(19) Uani 1 1 d . . . . .
H11A H 0.9147 0.5407 0.1614 0.080 Uiso 1 1 calc R U . . .
H11B H 0.8133 0.4753 0.1356 0.080 Uiso 1 1 calc R U . . .
H11C H 0.9141 0.4791 0.2261 0.080 Uiso 1 1 calc R U . . .
C12 C 1.1082(6) 0.4834(3) 0.1085(4) 0.0348(15) Uani 1 1 d . . . . .
C13 C 1.1325(7) 0.5550(3) 0.0947(4) 0.0503(19) Uani 1 1 d . . . . .
H13 H 1.0774 0.5919 0.1062 0.060 Uiso 1 1 calc R U . . .
C14 C 1.2407(7) 0.5675(4) 0.0636(4) 0.0533(19) Uani 1 1 d . . . . .
H14 H 1.2604 0.6147 0.0520 0.064 Uiso 1 1 calc R U . . .
C15 C 1.3241(7) 0.5133(4) 0.0482(4) 0.0521(19) Uani 1 1 d . . . . .
H15 H 1.4000 0.5249 0.0281 0.062 Uiso 1 1 calc R U . . .
C16 C 1.2984(6) 0.4442(3) 0.0615(3) 0.0424(17) Uani 1 1 d . . . . .
H16 H 1.3538 0.4073 0.0502 0.051 Uiso 1 1 calc R U . . .
C17 C 1.1876(6) 0.4305(3) 0.0922(3) 0.0308(15) Uani 1 1 d . . . . .
C18 C 1.1902(6) 0.2981(3) 0.1075(4) 0.0468(17) Uani 1 1 d . . . . .
H18A H 1.2694 0.3023 0.0853 0.070 Uiso 1 1 calc R U . . .
H18B H 1.2181 0.2777 0.1629 0.070 Uiso 1 1 calc R U . . .
H18C H 1.1223 0.2675 0.0717 0.070 Uiso 1 1 calc R U . . .
C19 C 1.0333(6) 0.0986(3) 0.1021(4) 0.0351(15) Uani 1 1 d . . . . .
C20 C 1.0654(7) 0.1433(3) -0.0299(4) 0.055(2) Uani 1 1 d . . . . .
H20A H 1.1181 0.1282 -0.0679 0.083 Uiso 1 1 calc R U . . .
H20B H 0.9686 0.1438 -0.0589 0.083 Uiso 1 1 calc R U . . .
H20C H 1.0939 0.1907 -0.0095 0.083 Uiso 1 1 calc R U . . .
C21 C 1.1786(6) 0.0378(3) 0.0471(4) 0.0422(17) Uani 1 1 d . . . . .
C22 C 1.2615(7) 0.0143(4) -0.0004(4) 0.059(2) Uani 1 1 d . . . . .
H22 H 1.2633 0.0371 -0.0503 0.070 Uiso 1 1 calc R U . . .
C23 C 1.3419(8) -0.0441(4) 0.0283(5) 0.073(3) Uani 1 1 d . . . . .
H23 H 1.4028 -0.0610 -0.0013 0.088 Uiso 1 1 calc R U . . .
C24 C 1.3341(7) -0.0780(4) 0.1000(6) 0.073(2) Uani 1 1 d . . . . .
H24 H 1.3882 -0.1188 0.1170 0.087 Uiso 1 1 calc R U . . .
C25 C 1.2512(7) -0.0553(4) 0.1476(5) 0.0543(19) Uani 1 1 d . . . . .
H25 H 1.2469 -0.0786 0.1968 0.065 Uiso 1 1 calc R U . . .
C26 C 1.1750(6) 0.0039(3) 0.1185(4) 0.0387(16) Uani 1 1 d . . . . .
C27 C 1.0547(7) 0.0259(3) 0.2293(4) 0.0534(19) Uani 1 1 d . . . . .
H27A H 1.1027 -0.0173 0.2520 0.080 Uiso 1 1 calc R U . . .
H27B H 1.0857 0.0650 0.2678 0.080 Uiso 1 1 calc R U . . .
H27C H 0.9568 0.0192 0.2208 0.080 Uiso 1 1 calc R U . . .
Cu1 Cu 0.90685(7) 0.30884(4) 0.16784(5) 0.0396(2) Uani 1 1 d . . . . .
Cu2 Cu 0.90290(8) 0.16367(4) 0.12779(5) 0.0473(2) Uani 1 1 d . . . . .
Fe1 Fe 0.69021(8) 0.23547(4) 0.11779(5) 0.0326(2) Uani 1 1 d . . . . .
Fe2 Fe 0.86039(8) 0.22333(5) 0.26959(5) 0.0335(2) Uani 1 1 d . . . . .
Fe3 Fe 0.59705(8) 0.21271(4) 0.24592(5) 0.0334(2) Uani 1 1 d . . . . .
N1 N 1.0079(5) 0.4516(3) 0.1388(3) 0.0374(13) Uani 1 1 d . . . . .
N2 N 1.1313(5) 0.3682(2) 0.1115(3) 0.0297(12) Uani 1 1 d . . . . .
N3 N 1.0884(5) 0.0948(3) 0.0384(3) 0.0361(13) Uani 1 1 d . . . . .
N4 N 1.0828(5) 0.0422(3) 0.1513(3) 0.0378(13) Uani 1 1 d . . . . .
O1 O 0.4240(5) 0.1956(3) 0.0132(3) 0.0659(15) Uani 1 1 d . . . . .
O2 O 0.6240(4) 0.3855(2) 0.1180(3) 0.0509(12) Uani 1 1 d . . . . .
O3 O 0.7954(5) 0.2465(2) -0.0285(3) 0.0669(15) Uani 1 1 d . . . . .
O4 O 0.8192(5) 0.3651(3) 0.3285(3) 0.0546(13) Uani 1 1 d . . . . .
O5 O 1.1524(5) 0.2242(3) 0.2792(3) 0.0585(14) Uani 1 1 d . . . . .
O6 O 0.9416(5) 0.1546(2) 0.4296(3) 0.0585(14) Uani 1 1 d . . . . .
O7 O 0.6228(5) 0.1764(3) 0.4183(3) 0.0610(14) Uani 1 1 d . . . . .
O8 O 0.3370(5) 0.1412(3) 0.1818(3) 0.0662(15) Uani 1 1 d . . . . .
O9 O 0.4859(5) 0.3536(3) 0.2584(3) 0.0637(15) Uani 1 1 d . . . . .
Se1 Se 0.72695(6) 0.13164(3) 0.19759(4) 0.03446(18) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.154(7) . ?
C1 Fe1 1.769(7) . ?
C2 O2 1.177(7) . ?
C2 Fe1 1.750(7) . ?
C2 Cu1 2.499(6) . ?
C3 O3 1.159(7) . ?
C3 Fe1 1.806(7) . ?
C3 Cu2 2.287(6) . ?
C4 O4 1.164(7) . ?
C4 Fe2 1.770(7) . ?
C5 O5 1.171(7) . ?
C5 Fe2 1.784(7) . ?
C5 Cu1 2.432(6) . ?
C6 O6 1.145(6) . ?
C6 Fe2 1.767(7) . ?
C7 O7 1.157(7) . ?
C7 Fe3 1.773(7) . ?
C8 O8 1.141(7) . ?
C8 Fe3 1.782(7) . ?
C9 O9 1.155(7) . ?
C9 Fe3 1.779(7) . ?
C10 N2 1.347(7) . ?
C10 N1 1.361(7) . ?
C10 Cu1 1.929(6) . ?
C11 N1 1.474(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.363(7) . ?
C12 N1 1.396(7) . ?
C12 C13 1.411(8) . ?
C13 C14 1.362(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.401(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.366(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(7) . ?
C16 H16 0.9500 . ?
C17 N2 1.389(7) . ?
C18 N2 1.468(7) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 N3 1.340(7) . ?
C19 N4 1.366(7) . ?
C19 Cu2 1.946(6) . ?
C20 N3 1.444(7) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C26 1.373(8) . ?
C21 C22 1.384(8) . ?
C21 N3 1.402(7) . ?
C22 C23 1.387(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(10) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.378(8) . ?
C25 H25 0.9500 . ?
C26 N4 1.412(7) . ?
C27 N4 1.451(7) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
Cu1 Fe2 2.4948(11) . ?
Cu1 Fe1 2.5604(12) . ?
Cu1 Cu2 2.8321(12) . ?
Cu2 Se1 2.4691(10) . ?
Cu2 Fe1 2.5309(12) . ?
Cu2 Fe2 2.7796(12) . ?
Fe1 Se1 2.3579(11) . ?
Fe1 Fe3 2.6150(12) . ?
Fe1 Fe2 2.6963(12) . ?
Fe2 Se1 2.3407(11) . ?
Fe2 Fe3 2.6200(13) . ?
Fe3 Se1 2.3145(10) . ?

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 C1 Fe1 178.4(6) . . ?
O2 C2 Fe1 175.2(6) . . ?
O2 C2 Cu1 112.5(4) . . ?
Fe1 C2 Cu1 71.7(2) . . ?
O3 C3 Fe1 166.4(6) . . ?
O3 C3 Cu2 118.2(5) . . ?
Fe1 C3 Cu2 75.4(2) . . ?
O4 C4 Fe2 177.0(6) . . ?
O5 C5 Fe2 169.6(5) . . ?
O5 C5 Cu1 117.4(5) . . ?
Fe2 C5 Cu1 70.7(2) . . ?
O6 C6 Fe2 177.0(6) . . ?
O7 C7 Fe3 177.7(6) . . ?
O8 C8 Fe3 177.5(6) . . ?
O9 C9 Fe3 175.4(6) . . ?
N2 C10 N1 104.9(5) . . ?
N2 C10 Cu1 125.8(4) . . ?
N1 C10 Cu1 129.3(4) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 N1 106.8(5) . . ?
C17 C12 C13 122.4(6) . . ?
N1 C12 C13 130.8(6) . . ?
C14 C13 C12 115.2(6) . . ?
C14 C13 H13 122.4 . . ?
C12 C13 H13 122.4 . . ?
C13 C14 C15 122.6(6) . . ?
C13 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C16 C15 C14 121.3(6) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 116.9(6) . . ?
C15 C16 H16 121.6 . . ?
C17 C16 H16 121.6 . . ?
C12 C17 C16 121.6(6) . . ?
C12 C17 N2 105.9(5) . . ?
C16 C17 N2 132.5(5) . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 N4 106.1(5) . . ?
N3 C19 Cu2 132.0(5) . . ?
N4 C19 Cu2 121.8(4) . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 121.2(7) . . ?
C26 C21 N3 106.5(5) . . ?
C22 C21 N3 132.2(7) . . ?
C21 C22 C23 116.8(7) . . ?
C21 C22 H22 121.6 . . ?
C23 C22 H22 121.6 . . ?
C22 C23 C24 120.6(7) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 123.0(7) . . ?
C25 C24 H24 118.5 . . ?
C23 C24 H24 118.5 . . ?
C26 C25 C24 115.0(7) . . ?
C26 C25 H25 122.5 . . ?
C24 C25 H25 122.5 . . ?
C21 C26 C25 123.3(6) . . ?
C21 C26 N4 106.0(5) . . ?
C25 C26 N4 130.6(6) . . ?
N4 C27 H27A 109.5 . . ?
N4 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N4 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C10 Cu1 C5 112.6(2) . . ?
C10 Cu1 Fe2 149.84(17) . . ?
C5 Cu1 Fe2 42.43(16) . . ?
C10 Cu1 C2 118.0(2) . . ?
C5 Cu1 C2 128.4(2) . . ?
Fe2 Cu1 C2 86.35(15) . . ?
C10 Cu1 Fe1 145.70(17) . . ?
C5 Cu1 Fe1 97.40(16) . . ?
Fe2 Cu1 Fe1 64.45(3) . . ?
C2 Cu1 Fe1 40.45(16) . . ?
C10 Cu1 Cu2 126.42(17) . . ?
C5 Cu1 Cu2 59.86(15) . . ?
Fe2 Cu1 Cu2 62.53(3) . . ?
C2 Cu1 Cu2 95.71(16) . . ?
Fe1 Cu1 Cu2 55.71(3) . . ?
C19 Cu2 C3 123.6(2) . . ?
C19 Cu2 Se1 125.21(18) . . ?
C3 Cu2 Se1 95.87(18) . . ?
C19 Cu2 Fe1 162.14(18) . . ?
C3 Cu2 Fe1 43.67(18) . . ?
Se1 Cu2 Fe1 56.26(3) . . ?
C19 Cu2 Fe2 136.09(18) . . ?
C3 Cu2 Fe2 98.55(17) . . ?
Se1 Cu2 Fe2 52.56(3) . . ?
Fe1 Cu2 Fe2 60.81(3) . . ?
C19 Cu2 Cu1 134.57(18) . . ?
C3 Cu2 Cu1 62.65(17) . . ?
Se1 Cu2 Cu1 95.27(3) . . ?
Fe1 Cu2 Cu1 56.70(3) . . ?
Fe2 Cu2 Cu1 52.78(3) . . ?
C2 Fe1 C1 96.6(3) . . ?
C2 Fe1 C3 97.8(3) . . ?
C1 Fe1 C3 93.8(3) . . ?
C2 Fe1 Se1 143.48(19) . . ?
C1 Fe1 Se1 95.7(2) . . ?
C3 Fe1 Se1 115.45(19) . . ?
C2 Fe1 Cu2 134.46(19) . . ?
C1 Fe1 Cu2 122.8(2) . . ?
C3 Fe1 Cu2 61.0(2) . . ?
Se1 Fe1 Cu2 60.55(3) . . ?
C2 Fe1 Cu1 67.89(19) . . ?
C1 Fe1 Cu1 158.2(2) . . ?
C3 Fe1 Cu1 74.2(2) . . ?
Se1 Fe1 Cu1 105.80(4) . . ?
Cu2 Fe1 Cu1 67.59(4) . . ?
C2 Fe1 Fe3 91.06(19) . . ?
C1 Fe1 Fe3 88.0(2) . . ?
C3 Fe1 Fe3 170.62(19) . . ?
Se1 Fe1 Fe3 55.18(3) . . ?
Cu2 Fe1 Fe3 110.43(4) . . ?
Cu1 Fe1 Fe3 106.78(4) . . ?
C2 Fe1 Fe2 98.18(19) . . ?
C1 Fe1 Fe2 144.0(2) . . ?
C3 Fe1 Fe2 116.3(2) . . ?
Se1 Fe1 Fe2 54.68(3) . . ?
Cu2 Fe1 Fe2 64.16(3) . . ?
Cu1 Fe1 Fe2 56.59(3) . . ?
Fe3 Fe1 Fe2 59.09(3) . . ?
C6 Fe2 C4 98.8(3) . . ?
C6 Fe2 C5 89.9(3) . . ?
C4 Fe2 C5 103.6(3) . . ?
C6 Fe2 Se1 96.5(2) . . ?
C4 Fe2 Se1 136.9(2) . . ?
C5 Fe2 Se1 116.5(2) . . ?
C6 Fe2 Cu1 151.4(2) . . ?
C4 Fe2 Cu1 72.33(19) . . ?
C5 Fe2 Cu1 66.9(2) . . ?
Se1 Fe2 Cu1 108.47(4) . . ?
C6 Fe2 Fe3 96.8(2) . . ?
C4 Fe2 Fe3 83.0(2) . . ?
C5 Fe2 Fe3 169.9(2) . . ?
Se1 Fe2 Fe3 55.28(3) . . ?
Cu1 Fe2 Fe3 108.60(4) . . ?
C6 Fe2 Fe1 149.5(2) . . ?
C4 Fe2 Fe1 96.2(2) . . ?
C5 Fe2 Fe1 112.11(19) . . ?
Se1 Fe2 Fe1 55.28(3) . . ?
Cu1 Fe2 Fe1 58.95(3) . . ?
Fe3 Fe2 Fe1 58.91(3) . . ?
C6 Fe2 Cu2 122.7(2) . . ?
C4 Fe2 Cu2 136.29(19) . . ?
C5 Fe2 Cu2 66.9(2) . . ?
Se1 Fe2 Cu2 56.89(3) . . ?
Cu1 Fe2 Cu2 64.69(3) . . ?
Fe3 Fe2 Cu2 102.99(4) . . ?
Fe1 Fe2 Cu2 55.03(3) . . ?
C7 Fe3 C9 96.1(3) . . ?
C7 Fe3 C8 96.4(3) . . ?
C9 Fe3 C8 97.7(3) . . ?
C7 Fe3 Se1 105.6(2) . . ?
C9 Fe3 Se1 152.4(2) . . ?
C8 Fe3 Se1 96.63(19) . . ?
C7 Fe3 Fe1 153.5(2) . . ?
C9 Fe3 Fe1 96.73(19) . . ?
C8 Fe3 Fe1 104.7(2) . . ?
Se1 Fe3 Fe1 56.76(3) . . ?
C7 Fe3 Fe2 92.05(19) . . ?
C9 Fe3 Fe2 107.0(2) . . ?
C8 Fe3 Fe2 152.85(19) . . ?
Se1 Fe3 Fe2 56.22(3) . . ?
Fe1 Fe3 Fe2 62.00(3) . . ?
C10 N1 C12 110.5(5) . . ?
C10 N1 C11 124.6(5) . . ?
C12 N1 C11 124.9(5) . . ?
C10 N2 C17 111.9(5) . . ?
C10 N2 C18 123.9(5) . . ?
C17 N2 C18 124.0(5) . . ?
C19 N3 C21 111.2(5) . . ?
C19 N3 C20 126.2(5) . . ?
C21 N3 C20 122.6(5) . . ?
C19 N4 C26 110.2(5) . . ?
C19 N4 C27 125.8(5) . . ?
C26 N4 C27 123.8(5) . . ?
Fe3 Se1 Fe2 68.50(4) . . ?
Fe3 Se1 Fe1 68.06(3) . . ?
Fe2 Se1 Fe1 70.04(4) . . ?
Fe3 Se1 Cu2 124.12(4) . . ?
Fe2 Se1 Cu2 70.55(3) . . ?
Fe1 Se1 Cu2 63.20(3) . . ?

_refine_diff_density_max         0.585
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.098

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1909694'
loop_
_audit_author_name
_audit_author_address
'Yu-Hsin Liu'
;NTNU University
Taiwan
;
_audit_update_record             
;
2019-04-12 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 Cl4 Cu2 Fe3 N4 O9 Se'
_chemical_formula_sum            'C19 H12 Cl4 Cu2 Fe3 N4 O9 Se'
_chemical_formula_weight         955.72

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3228(5)
_cell_length_b                   23.2450(16)
_cell_length_c                   15.4952(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.387(3)
_cell_angle_gamma                90
_cell_volume                     2916.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6598
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      24.97

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.177
_exptl_crystal_F_000             1856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    4.560
_shelx_estimated_absorpt_T_min   0.494
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4941
_exptl_absorpt_correction_T_max  0.9143
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18395
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.752
_diffrn_reflns_theta_max         25.034
_diffrn_reflns_theta_full        25.034
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             5073
_reflns_number_gt                3919
_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 APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.1353P)²+22.7936P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5073
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0801
_refine_ls_wR_factor_ref         0.2301
_refine_ls_wR_factor_gt          0.2146
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5849(13) 0.6798(4) 0.4222(7) 0.030(2) Uani 1 1 d . . . . .
C2 C 0.8495(14) 0.6266(4) 0.3584(6) 0.028(2) Uani 1 1 d . . . . .
C3 C 0.6266(12) 0.5716(4) 0.4343(7) 0.025(2) Uani 1 1 d . . . . .
C4 C 0.7449(13) 0.5614(4) 0.1738(6) 0.031(2) Uani 1 1 d . . . . .
C5 C 0.5189(12) 0.4937(4) 0.2337(7) 0.029(2) Uani 1 1 d . . . . .
C6 C 0.4354(14) 0.5554(4) 0.0931(7) 0.035(3) Uani 1 1 d . . . . .
C7 C 0.4000(13) 0.6826(4) 0.0899(8) 0.032(2) Uani 1 1 d . . . . .
C8 C 0.4912(12) 0.7503(4) 0.2221(6) 0.026(2) Uani 1 1 d . . . . .
C9 C 0.7226(13) 0.6858(4) 0.1651(6) 0.028(2) Uani 1 1 d . . . . .
C10 C 0.8712(11) 0.7900(4) 0.3613(6) 0.025(2) Uani 1 1 d . . . . .
C11 C 0.6688(12) 0.8475(5) 0.4233(7) 0.033(2) Uani 1 1 d . . . . .
H11A H 0.6093 0.8108 0.4173 0.049 Uiso 1 1 calc R U . . .
H11B H 0.6948 0.8595 0.4855 0.049 Uiso 1 1 calc R U . . .
H11C H 0.5998 0.8767 0.3869 0.049 Uiso 1 1 calc R U . . .
C12 C 0.9371(12) 0.8825(4) 0.3921(6) 0.022(2) Uani 1 1 d . . . . .
C13 C 1.0568(12) 0.8596(4) 0.3573(6) 0.025(2) Uani 1 1 d . . . . .
C14 C 1.1191(12) 0.7615(4) 0.3086(7) 0.030(2) Uani 1 1 d . . . . .
H14A H 1.2179 0.7810 0.2990 0.045 Uiso 1 1 calc R U . . .
H14B H 1.1519 0.7306 0.3521 0.045 Uiso 1 1 calc R U . . .
H14C H 1.0571 0.7452 0.2524 0.045 Uiso 1 1 calc R U . . .
C15 C 0.8938(12) 0.4576(4) 0.3761(7) 0.031(2) Uani 1 1 d . . . . .
C16 C 1.1330(13) 0.4882(5) 0.3173(7) 0.035(2) Uani 1 1 d . . . . .
H16A H 1.2334 0.4700 0.3073 0.052 Uiso 1 1 calc R U . . .
H16B H 1.0660 0.5023 0.2607 0.052 Uiso 1 1 calc R U . . .
H16C H 1.1632 0.5204 0.3586 0.052 Uiso 1 1 calc R U . . .
C17 C 1.0795(11) 0.3890(4) 0.3706(6) 0.022(2) Uani 1 1 d . . . . .
C18 C 0.9635(12) 0.3666(4) 0.4071(6) 0.023(2) Uani 1 1 d . . . . .
C19 C 0.7020(13) 0.4011(5) 0.4442(8) 0.037(3) Uani 1 1 d . . . . .
H19A H 0.6973 0.3614 0.4648 0.055 Uiso 1 1 calc R U . . .
H19B H 0.7059 0.4276 0.4937 0.055 Uiso 1 1 calc R U . . .
H19C H 0.6036 0.4091 0.3971 0.055 Uiso 1 1 calc R U . . .
N1 N 0.8238(9) 0.8405(3) 0.3931(5) 0.0221(17) Uani 1 1 d . . . . .
N2 N 1.0166(9) 0.8024(3) 0.3412(5) 0.0213(17) Uani 1 1 d . . . . .
N3 N 1.0387(9) 0.4463(3) 0.3546(5) 0.0235(17) Uani 1 1 d . . . . .
N4 N 0.8495(9) 0.4086(3) 0.4096(5) 0.0259(18) Uani 1 1 d . . . . .
O1 O 0.5416(12) 0.7119(3) 0.4712(6) 0.053(2) Uani 1 1 d . . . . .
O2 O 0.9926(10) 0.6261(3) 0.3639(6) 0.0396(19) Uani 1 1 d . . . . .
O3 O 0.6192(10) 0.5420(3) 0.4940(5) 0.0434(19) Uani 1 1 d . . . . .
O4 O 0.8717(10) 0.5586(4) 0.1514(6) 0.051(2) Uani 1 1 d . . . . .
O5 O 0.4832(10) 0.4461(3) 0.2456(5) 0.0414(19) Uani 1 1 d . . . . .
O6 O 0.3588(13) 0.5465(4) 0.0229(5) 0.066(3) Uani 1 1 d . . . . .
O7 O 0.3147(11) 0.6876(3) 0.0217(5) 0.050(2) Uani 1 1 d . . . . .
O8 O 0.4559(10) 0.7985(3) 0.2299(5) 0.0425(19) Uani 1 1 d . . . . .
O9 O 0.8427(10) 0.6925(4) 0.1399(5) 0.048(2) Uani 1 1 d . . . . .
Fe1 Fe 0.63351(17) 0.62430(5) 0.35400(8) 0.0189(4) Uani 1 1 d . . . . .
Fe2 Fe 0.55160(16) 0.56571(5) 0.20273(8) 0.0204(4) Uani 1 1 d . . . . .
Fe3 Fe 0.53321(16) 0.67809(5) 0.19794(8) 0.0203(4) Uani 1 1 d . . . . .
Cu1 Cu 0.74134(15) 0.72074(5) 0.33117(8) 0.0294(4) Uani 1 1 d . . . . .
Cu2 Cu 0.75825(16) 0.52665(6) 0.33846(9) 0.0362(4) Uani 1 1 d . . . . .
Se1 Se 0.37029(11) 0.61897(4) 0.26235(7) 0.0252(3) Uani 1 1 d . . . . .
Cl1 Cl 0.9154(4) 0.95136(11) 0.42502(18) 0.0402(7) Uani 1 1 d . . . . .
Cl2 Cl 1.2248(3) 0.89043(12) 0.33247(17) 0.0331(6) Uani 1 1 d . . . . .
Cl3 Cl 1.2491(3) 0.35856(12) 0.34599(17) 0.0336(6) Uani 1 1 d . . . . .
Cl4 Cl 0.9457(3) 0.29738(11) 0.44149(18) 0.0379(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.180(12) . ?
C1 Fe1 1.772(10) . ?
C1 Cu1 2.333(10) . ?
C2 O2 1.175(13) . ?
C2 Fe1 1.783(11) . ?
C2 Cu1 2.367(10) . ?
C2 Cu2 2.441(9) . ?
C3 O3 1.167(12) . ?
C3 Fe1 1.756(10) . ?
C3 Cu2 2.292(10) . ?
C4 O4 1.187(13) . ?
C4 Fe2 1.770(11) . ?
C5 O5 1.172(12) . ?
C5 Fe2 1.779(11) . ?
C5 Cu2 2.385(10) . ?
C6 O6 1.145(13) . ?
C6 Fe2 1.766(11) . ?
C7 O7 1.135(13) . ?
C7 Fe3 1.784(11) . ?
C8 O8 1.172(12) . ?
C8 Fe3 1.772(10) . ?
C8 Cu1 2.456(9) . ?
C9 O9 1.164(12) . ?
C9 Fe3 1.774(11) . ?
C10 N2 1.348(11) . ?
C10 N1 1.366(12) . ?
C10 Cu1 1.935(10) . ?
C11 N1 1.479(12) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.348(15) . ?
C12 N1 1.360(12) . ?
C12 Cl1 1.703(9) . ?
C13 N2 1.380(12) . ?
C13 Cl2 1.692(10) . ?
C14 N2 1.444(12) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N4 1.339(13) . ?
C15 N3 1.349(12) . ?
C15 Cu2 1.970(10) . ?
C16 N3 1.451(13) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.332(14) . ?
C17 N3 1.385(12) . ?
C17 Cl3 1.699(9) . ?
C18 N4 1.369(12) . ?
C18 Cl4 1.711(10) . ?
C19 N4 1.459(12) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
Fe1 Se1 2.3219(16) . ?
Fe1 Cu1 2.4703(17) . ?
Fe1 Cu2 2.5306(18) . ?
Fe1 Fe2 2.6597(18) . ?
Fe1 Fe3 2.6784(18) . ?
Fe2 Se1 2.3041(16) . ?
Fe2 Cu2 2.5555(18) . ?
Fe2 Fe3 2.6169(19) . ?
Fe3 Se1 2.3130(16) . ?
Fe3 Cu1 2.5669(17) . ?

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 C1 Fe1 172.1(9) . . ?
O1 C1 Cu1 115.3(7) . . ?
Fe1 C1 Cu1 72.6(4) . . ?
O2 C2 Fe1 177.1(9) . . ?
O2 C2 Cu1 111.0(7) . . ?
Fe1 C2 Cu1 71.5(4) . . ?
O2 C2 Cu2 106.3(7) . . ?
Fe1 C2 Cu2 71.7(3) . . ?
Cu1 C2 Cu2 139.7(5) . . ?
O3 C3 Fe1 172.0(9) . . ?
O3 C3 Cu2 111.4(7) . . ?
Fe1 C3 Cu2 76.1(4) . . ?
O4 C4 Fe2 177.7(9) . . ?
O5 C5 Fe2 172.4(9) . . ?
O5 C5 Cu2 113.5(7) . . ?
Fe2 C5 Cu2 74.1(4) . . ?
O6 C6 Fe2 177.3(10) . . ?
O7 C7 Fe3 177.4(9) . . ?
O8 C8 Fe3 173.7(9) . . ?
O8 C8 Cu1 112.9(7) . . ?
Fe3 C8 Cu1 72.7(3) . . ?
O9 C9 Fe3 176.5(9) . . ?
N2 C10 N1 104.5(8) . . ?
N2 C10 Cu1 127.1(7) . . ?
N1 C10 Cu1 127.6(7) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N1 107.5(8) . . ?
C13 C12 Cl1 129.1(8) . . ?
N1 C12 Cl1 123.3(8) . . ?
C12 C13 N2 106.4(8) . . ?
C12 C13 Cl2 130.5(8) . . ?
N2 C13 Cl2 123.1(8) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 N3 105.8(8) . . ?
N4 C15 Cu2 128.2(7) . . ?
N3 C15 Cu2 124.6(8) . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N3 106.3(8) . . ?
C18 C17 Cl3 130.8(8) . . ?
N3 C17 Cl3 122.8(7) . . ?
C17 C18 N4 108.0(8) . . ?
C17 C18 Cl4 128.5(8) . . ?
N4 C18 Cl4 123.4(7) . . ?
N4 C19 H19A 109.5 . . ?
N4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 N1 C10 110.7(8) . . ?
C12 N1 C11 125.6(8) . . ?
C10 N1 C11 123.7(8) . . ?
C10 N2 C13 110.9(8) . . ?
C10 N2 C14 125.1(8) . . ?
C13 N2 C14 124.0(8) . . ?
C15 N3 C17 109.8(8) . . ?
C15 N3 C16 124.4(8) . . ?
C17 N3 C16 125.7(8) . . ?
C15 N4 C18 110.0(8) . . ?
C15 N4 C19 125.1(8) . . ?
C18 N4 C19 124.9(8) . . ?
C3 Fe1 C1 92.0(5) . . ?
C3 Fe1 C2 101.0(4) . . ?
C1 Fe1 C2 108.8(5) . . ?
C3 Fe1 Se1 102.4(3) . . ?
C1 Fe1 Se1 95.2(4) . . ?
C2 Fe1 Se1 145.6(3) . . ?
C3 Fe1 Cu1 143.8(3) . . ?
C1 Fe1 Cu1 64.3(3) . . ?
C2 Fe1 Cu1 65.3(3) . . ?
Se1 Fe1 Cu1 106.46(6) . . ?
C3 Fe1 Cu2 61.5(3) . . ?
C1 Fe1 Cu2 149.9(3) . . ?
C2 Fe1 Cu2 66.3(3) . . ?
Se1 Fe1 Cu2 104.11(6) . . ?
Cu1 Fe1 Cu2 129.03(7) . . ?
C3 Fe1 Fe2 102.9(3) . . ?
C1 Fe1 Fe2 148.3(4) . . ?
C2 Fe1 Fe2 95.7(3) . . ?
Se1 Fe1 Fe2 54.59(5) . . ?
Cu1 Fe1 Fe2 111.47(6) . . ?
Cu2 Fe1 Fe2 58.93(5) . . ?
C3 Fe1 Fe3 155.6(3) . . ?
C1 Fe1 Fe3 97.6(3) . . ?
C2 Fe1 Fe3 97.0(3) . . ?
Se1 Fe1 Fe3 54.54(4) . . ?
Cu1 Fe1 Fe3 59.65(5) . . ?
Cu2 Fe1 Fe3 112.45(6) . . ?
Fe2 Fe1 Fe3 58.71(5) . . ?
C6 Fe2 C4 94.4(5) . . ?
C6 Fe2 C5 92.7(5) . . ?
C4 Fe2 C5 102.7(5) . . ?
C6 Fe2 Se1 101.2(4) . . ?
C4 Fe2 Se1 148.2(3) . . ?
C5 Fe2 Se1 104.0(3) . . ?
C6 Fe2 Cu2 149.1(3) . . ?
C4 Fe2 Cu2 73.1(3) . . ?
C5 Fe2 Cu2 63.9(3) . . ?
Se1 Fe2 Cu2 103.85(6) . . ?
C6 Fe2 Fe3 95.3(3) . . ?
C4 Fe2 Fe3 95.7(3) . . ?
C5 Fe2 Fe3 159.2(3) . . ?
Se1 Fe2 Fe3 55.63(4) . . ?
Cu2 Fe2 Fe3 113.69(6) . . ?
C6 Fe2 Fe1 152.7(3) . . ?
C4 Fe2 Fe1 100.9(3) . . ?
C5 Fe2 Fe1 105.5(3) . . ?
Se1 Fe2 Fe1 55.22(5) . . ?
Cu2 Fe2 Fe1 58.01(5) . . ?
Fe3 Fe2 Fe1 61.00(5) . . ?
C8 Fe3 C9 101.4(5) . . ?
C8 Fe3 C7 91.9(4) . . ?
C9 Fe3 C7 97.2(5) . . ?
C8 Fe3 Se1 107.9(3) . . ?
C9 Fe3 Se1 146.3(3) . . ?
C7 Fe3 Se1 98.1(3) . . ?
C8 Fe3 Cu1 66.0(3) . . ?
C9 Fe3 Cu1 73.3(3) . . ?
C7 Fe3 Cu1 152.8(3) . . ?
Se1 Fe3 Cu1 103.67(6) . . ?
C8 Fe3 Fe2 162.3(3) . . ?
C9 Fe3 Fe2 93.4(3) . . ?
C7 Fe3 Fe2 96.0(3) . . ?
Se1 Fe3 Fe2 55.31(5) . . ?
Cu1 Fe3 Fe2 109.79(6) . . ?
C8 Fe3 Fe1 106.7(3) . . ?
C9 Fe3 Fe1 101.2(3) . . ?
C7 Fe3 Fe1 150.5(3) . . ?
Se1 Fe3 Fe1 54.85(5) . . ?
Cu1 Fe3 Fe1 56.15(5) . . ?
Fe2 Fe3 Fe1 60.29(5) . . ?
C10 Cu1 C1 123.6(4) . . ?
C10 Cu1 C2 123.9(4) . . ?
C1 Cu1 C2 75.9(4) . . ?
C10 Cu1 C8 105.7(4) . . ?
C1 Cu1 C8 91.5(3) . . ?
C2 Cu1 C8 127.4(4) . . ?
C10 Cu1 Fe1 157.2(3) . . ?
C1 Cu1 Fe1 43.2(3) . . ?
C2 Cu1 Fe1 43.2(3) . . ?
C8 Cu1 Fe1 94.2(2) . . ?
C10 Cu1 Fe3 138.6(3) . . ?
C1 Cu1 Fe3 87.8(3) . . ?
C2 Cu1 Fe3 86.8(3) . . ?
C8 Cu1 Fe3 41.2(2) . . ?
Fe1 Cu1 Fe3 64.21(5) . . ?
C15 Cu2 C3 120.4(4) . . ?
C15 Cu2 C5 105.7(4) . . ?
C3 Cu2 C5 97.9(3) . . ?
C15 Cu2 C2 126.7(4) . . ?
C3 Cu2 C2 70.4(3) . . ?
C5 Cu2 C2 125.3(4) . . ?
C15 Cu2 Fe1 157.2(3) . . ?
C3 Cu2 Fe1 42.3(2) . . ?
C5 Cu2 Fe1 93.2(2) . . ?
C2 Cu2 Fe1 42.0(3) . . ?
C15 Cu2 Fe2 139.7(3) . . ?
C3 Cu2 Fe2 92.3(3) . . ?
C5 Cu2 Fe2 42.0(2) . . ?
C2 Cu2 Fe2 84.1(3) . . ?
Fe1 Cu2 Fe2 63.06(5) . . ?
Fe2 Se1 Fe3 69.05(5) . . ?
Fe2 Se1 Fe1 70.19(5) . . ?
Fe3 Se1 Fe1 70.60(5) . . ?

_refine_diff_density_max         5.136
_refine_diff_density_min         -1.603
_refine_diff_density_rms         0.251

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1909693'
loop_
_audit_author_name
_audit_author_address
'Yu-Hsin Liu'
;NTNU University
Taiwan
;
_audit_update_record             
;
2019-04-12 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H36 Cu2 Fe3 N4 O9 Se'
_chemical_formula_sum            'C35 H36 Cu2 Fe3 N4 O9 Se'
_chemical_formula_weight         1030.27

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   12.115(5)
_cell_length_b                   12.288(6)
_cell_length_c                   15.442(7)
_cell_angle_alpha                107.607(5)
_cell_angle_beta                 99.965(6)
_cell_angle_gamma                108.614(4)
_cell_volume                     1981.9(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3678
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      25.61

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.340
_exptl_absorpt_coefficient_mu    3.102
_shelx_estimated_absorpt_T_min   0.266
_shelx_estimated_absorpt_T_max   0.419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2663
_exptl_absorpt_correction_T_max  0.4186
_exptl_absorpt_process_details   'SADABS, 2003'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17582
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.858
_diffrn_reflns_theta_max         25.117
_diffrn_reflns_theta_full        25.117
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             7005
_reflns_number_gt                4493
_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 APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0505P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7005
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_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
C1 C 0.3489(5) 0.5440(5) 0.4575(4) 0.0466(15) Uani 1 1 d . . . . .
C2 C 0.3152(5) 0.3111(5) 0.3895(4) 0.0391(14) Uani 1 1 d . . . . .
C3 C 0.4665(5) 0.4826(5) 0.3400(4) 0.0402(14) Uani 1 1 d . . . . .
C4 C 0.1309(5) 0.1509(6) 0.1328(4) 0.0469(15) Uani 1 1 d . . . . .
C5 C 0.2655(6) 0.3377(5) 0.0883(4) 0.0535(17) Uani 1 1 d . . . . .
C6 C 0.0382(6) 0.2911(5) 0.0768(4) 0.0509(16) Uani 1 1 d . . . . .
C7 C 0.4168(6) 0.5923(5) 0.2044(4) 0.0470(16) Uani 1 1 d . . . . .
C8 C 0.1897(6) 0.5799(5) 0.1519(5) 0.064(2) Uani 1 1 d . . . . .
C9 C 0.3278(5) 0.6973(6) 0.3351(5) 0.0448(15) Uani 1 1 d . . . . .
C10 C 0.0002(6) 0.1247(5) 0.3296(4) 0.0462(16) Uani 1 1 d . . . . .
C11 C -0.0625(6) 0.2885(5) 0.4195(4) 0.0531(17) Uani 1 1 d . . . . .
H11 H 0.0074 0.3406 0.4042 0.064 Uiso 1 1 calc R U . . .
C12 C -0.1745(7) 0.3001(6) 0.3715(5) 0.074(2) Uani 1 1 d . . . . .
H12A H -0.1662 0.3865 0.3988 0.111 Uiso 1 1 calc R U . . .
H12B H -0.1841 0.2758 0.3032 0.111 Uiso 1 1 calc R U . . .
H12C H -0.2463 0.2457 0.3812 0.111 Uiso 1 1 calc R U . . .
C13 C -0.0310(7) 0.3362(6) 0.5272(4) 0.089(3) Uani 1 1 d . . . . .
H13A H -0.0252 0.4219 0.5520 0.133 Uiso 1 1 calc R U . . .
H13B H -0.0948 0.2836 0.5455 0.133 Uiso 1 1 calc R U . . .
H13C H 0.0474 0.3339 0.5538 0.133 Uiso 1 1 calc R U . . .
C14 C -0.1553(6) 0.0578(5) 0.3915(4) 0.0514(18) Uani 1 1 d . . . . .
C15 C -0.2467(6) 0.0471(6) 0.4337(4) 0.067(2) Uani 1 1 d . . . . .
H15 H -0.2652 0.1163 0.4630 0.080 Uiso 1 1 calc R U . . .
C16 C -0.3110(7) -0.0703(7) 0.4316(4) 0.080(3) Uani 1 1 d . . . . .
H16 H -0.3744 -0.0820 0.4608 0.096 Uiso 1 1 calc R U . . .
C17 C -0.2840(7) -0.1693(6) 0.3878(5) 0.081(3) Uani 1 1 d . . . . .
H17 H -0.3303 -0.2482 0.3873 0.097 Uiso 1 1 calc R U . . .
C18 C -0.1947(7) -0.1602(5) 0.3452(4) 0.071(2) Uani 1 1 d . . . . .
H18 H -0.1774 -0.2302 0.3159 0.085 Uiso 1 1 calc R U . . .
C19 C -0.1289(6) -0.0428(5) 0.3463(4) 0.0516(17) Uani 1 1 d . . . . .
C20 C 0.0275(6) -0.0730(5) 0.2593(4) 0.0544(17) Uani 1 1 d . . . . .
H20 H 0.0932 -0.0154 0.2439 0.065 Uiso 1 1 calc R U . . .
C21 C 0.0901(7) -0.1205(7) 0.3267(5) 0.086(2) Uani 1 1 d . . . . .
H21A H 0.1305 -0.1697 0.2933 0.128 Uiso 1 1 calc R U . . .
H21B H 0.1507 -0.0496 0.3825 0.128 Uiso 1 1 calc R U . . .
H21C H 0.0287 -0.1725 0.3472 0.128 Uiso 1 1 calc R U . . .
C22 C -0.0588(6) -0.1731(5) 0.1668(4) 0.0615(18) Uani 1 1 d . . . . .
H22A H -0.0157 -0.2201 0.1347 0.092 Uiso 1 1 calc R U . . .
H22B H -0.1269 -0.2292 0.1790 0.092 Uiso 1 1 calc R U . . .
H22C H -0.0902 -0.1353 0.1261 0.092 Uiso 1 1 calc R U . . .
C23 C 0.4762(5) 0.2134(5) 0.1844(3) 0.0379(14) Uani 1 1 d . . . . .
C24 C 0.3868(5) 0.0396(5) 0.2336(4) 0.0413(14) Uani 1 1 d . . . . .
H24 H 0.3320 0.0847 0.2462 0.050 Uiso 1 1 calc R U . . .
C25 C 0.3059(6) -0.0917(5) 0.1623(4) 0.0562(17) Uani 1 1 d . . . . .
H25A H 0.2487 -0.1340 0.1908 0.084 Uiso 1 1 calc R U . . .
H25B H 0.2602 -0.0878 0.1051 0.084 Uiso 1 1 calc R U . . .
H25C H 0.3568 -0.1377 0.1449 0.084 Uiso 1 1 calc R U . . .
C26 C 0.4503(6) 0.0423(5) 0.3287(4) 0.0559(17) Uani 1 1 d . . . . .
H26A H 0.3895 -0.0037 0.3530 0.084 Uiso 1 1 calc R U . . .
H26B H 0.5091 0.0037 0.3202 0.084 Uiso 1 1 calc R U . . .
H26C H 0.4932 0.1287 0.3742 0.084 Uiso 1 1 calc R U . . .
C27 C 0.5640(5) 0.0743(5) 0.1634(4) 0.0436(15) Uani 1 1 d . . . . .
C28 C 0.6004(6) -0.0231(5) 0.1609(4) 0.0516(16) Uani 1 1 d . . . . .
H28 H 0.5603 -0.0848 0.1828 0.062 Uiso 1 1 calc R U . . .
C29 C 0.6952(7) -0.0264(6) 0.1262(4) 0.0614(19) Uani 1 1 d . . . . .
H29 H 0.7200 -0.0932 0.1225 0.074 Uiso 1 1 calc R U . . .
C30 C 0.7577(6) 0.0642(6) 0.0955(4) 0.0604(18) Uani 1 1 d . . . . .
H30 H 0.8247 0.0592 0.0729 0.073 Uiso 1 1 calc R U . . .
C31 C 0.7227(6) 0.1607(6) 0.0979(4) 0.0547(17) Uani 1 1 d . . . . .
H31 H 0.7634 0.2223 0.0761 0.066 Uiso 1 1 calc R U . . .
C32 C 0.6253(5) 0.1650(5) 0.1335(4) 0.0417(14) Uani 1 1 d . . . . .
C33 C 0.6070(5) 0.3670(5) 0.1323(4) 0.0434(15) Uani 1 1 d . . . . .
H33 H 0.5493 0.4062 0.1504 0.052 Uiso 1 1 calc R U . . .
C34 C 0.7343(6) 0.4568(5) 0.1996(5) 0.0613(18) Uani 1 1 d . . . . .
H34A H 0.7581 0.5343 0.1885 0.092 Uiso 1 1 calc R U . . .
H34B H 0.7334 0.4746 0.2657 0.092 Uiso 1 1 calc R U . . .
H34C H 0.7930 0.4190 0.1876 0.092 Uiso 1 1 calc R U . . .
C35 C 0.5953(7) 0.3462(6) 0.0281(4) 0.066(2) Uani 1 1 d . . . . .
H35A H 0.6212 0.4266 0.0214 0.099 Uiso 1 1 calc R U . . .
H35B H 0.6470 0.3033 0.0063 0.099 Uiso 1 1 calc R U . . .
H35C H 0.5101 0.2953 -0.0104 0.099 Uiso 1 1 calc R U . . .
N1 N -0.0719(5) 0.1587(4) 0.3800(3) 0.0486(14) Uani 1 1 d . . . . .
N2 N -0.0334(4) 0.0013(4) 0.3108(3) 0.0499(14) Uani 1 1 d . . . . .
N3 N 0.4737(4) 0.1068(4) 0.1949(3) 0.0392(11) Uani 1 1 d . . . . .
N4 N 0.5693(4) 0.2492(4) 0.1479(3) 0.0399(11) Uani 1 1 d . . . . .
O1 O 0.3737(4) 0.6214(4) 0.5306(3) 0.0637(12) Uani 1 1 d . . . . .
O2 O 0.3333(4) 0.2465(4) 0.4258(3) 0.0531(11) Uani 1 1 d . . . . .
O3 O 0.5708(4) 0.5287(3) 0.3510(3) 0.0503(11) Uani 1 1 d . . . . .
O4 O 0.1047(4) 0.0442(4) 0.1000(3) 0.0640(13) Uani 1 1 d . . . . .
O5 O 0.3159(4) 0.3456(4) 0.0313(3) 0.0634(13) Uani 1 1 d . . . . .
O6 O -0.0465(4) 0.2777(4) 0.0231(3) 0.0697(14) Uani 1 1 d . . . . .
O7 O 0.5042(4) 0.6217(4) 0.1815(3) 0.0638(13) Uani 1 1 d . . . . .
O8 O 0.1295(5) 0.5964(4) 0.0961(4) 0.0959(19) Uani 1 1 d . . . . .
O9 O 0.3556(4) 0.7902(4) 0.3982(3) 0.0661(13) Uani 1 1 d . . . . .
Fe1 Fe 0.31490(7) 0.42890(6) 0.34466(5) 0.0326(2) Uani 1 1 d . . . . .
Fe2 Fe 0.17134(7) 0.31210(7) 0.16086(5) 0.0389(2) Uani 1 1 d . . . . .
Fe3 Fe 0.28225(7) 0.55441(7) 0.23976(6) 0.0401(2) Uani 1 1 d . . . . .
Cu1 Cu 0.11448(6) 0.23263(6) 0.28950(5) 0.0488(2) Uani 1 1 d . . . . .
Cu2 Cu 0.36684(6) 0.29196(6) 0.21577(5) 0.0401(2) Uani 1 1 d . . . . .
Se1 Se 0.12895(5) 0.43861(5) 0.28561(4) 0.04048(17) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.149(6) . ?
C1 Fe1 1.759(6) . ?
C2 O2 1.154(6) . ?
C2 Fe1 1.784(6) . ?
C2 Cu1 2.352(5) . ?
C3 O3 1.165(6) . ?
C3 Fe1 1.765(6) . ?
C3 Cu2 2.302(5) . ?
C4 O4 1.163(6) . ?
C4 Fe2 1.771(6) . ?
C4 Cu1 2.393(6) . ?
C5 O5 1.164(7) . ?
C5 Fe2 1.755(7) . ?
C5 Cu2 2.444(6) . ?
C6 O6 1.132(6) . ?
C6 Fe2 1.778(6) . ?
C7 O7 1.158(7) . ?
C7 Fe3 1.774(7) . ?
C8 O8 1.139(7) . ?
C8 Fe3 1.775(7) . ?
C9 O9 1.155(6) . ?
C9 Fe3 1.758(7) . ?
C10 N1 1.347(7) . ?
C10 N2 1.360(7) . ?
C10 Cu1 1.919(6) . ?
C11 N1 1.483(7) . ?
C11 C12 1.500(9) . ?
C11 C13 1.517(8) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.370(9) . ?
C14 C19 1.388(9) . ?
C14 N1 1.408(6) . ?
C15 C16 1.391(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.370(10) . ?
C16 H16 0.9500 . ?
C17 C18 1.351(10) . ?
C17 H17 0.9500 . ?
C18 C19 1.401(7) . ?
C18 H18 0.9500 . ?
C19 N2 1.390(7) . ?
C20 N2 1.485(8) . ?
C20 C22 1.498(8) . ?
C20 C21 1.541(8) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 N4 1.357(6) . ?
C23 N3 1.358(6) . ?
C23 Cu2 1.917(6) . ?
C24 N3 1.453(6) . ?
C24 C25 1.522(7) . ?
C24 C26 1.521(8) . ?
C24 H24 1.0000 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C32 1.381(7) . ?
C27 N3 1.393(7) . ?
C27 C28 1.394(8) . ?
C28 C29 1.356(8) . ?
C28 H28 0.9500 . ?
C29 C30 1.394(9) . ?
C29 H29 0.9500 . ?
C30 C31 1.374(8) . ?
C30 H30 0.9500 . ?
C31 C32 1.394(8) . ?
C31 H31 0.9500 . ?
C32 N4 1.394(7) . ?
C33 N4 1.478(6) . ?
C33 C35 1.525(7) . ?
C33 C34 1.530(8) . ?
C33 H33 1.0000 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
Fe1 Se1 2.3339(12) . ?
Fe1 Cu2 2.5044(12) . ?
Fe1 Cu1 2.5963(12) . ?
Fe1 Fe3 2.6151(13) . ?
Fe1 Fe2 2.7155(14) . ?
Fe2 Se1 2.3307(12) . ?
Fe2 Cu2 2.4891(14) . ?
Fe2 Cu1 2.5675(13) . ?
Fe2 Fe3 2.6155(15) . ?
Fe3 Se1 2.3137(11) . ?
Cu1 Se1 2.5007(14) . ?

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 C1 Fe1 178.1(6) . . ?
O2 C2 Fe1 169.8(5) . . ?
O2 C2 Cu1 113.8(4) . . ?
Fe1 C2 Cu1 76.4(2) . . ?
O3 C3 Fe1 169.9(5) . . ?
O3 C3 Cu2 114.5(4) . . ?
Fe1 C3 Cu2 74.71(19) . . ?
O4 C4 Fe2 169.2(5) . . ?
O4 C4 Cu1 116.2(4) . . ?
Fe2 C4 Cu1 74.4(2) . . ?
O5 C5 Fe2 172.1(5) . . ?
O5 C5 Cu2 114.8(5) . . ?
Fe2 C5 Cu2 70.5(2) . . ?
O6 C6 Fe2 179.9(7) . . ?
O7 C7 Fe3 177.1(5) . . ?
O8 C8 Fe3 179.2(7) . . ?
O9 C9 Fe3 178.6(5) . . ?
N1 C10 N2 104.8(5) . . ?
N1 C10 Cu1 124.5(4) . . ?
N2 C10 Cu1 130.5(5) . . ?
N1 C11 C12 111.0(5) . . ?
N1 C11 C13 110.7(5) . . ?
C12 C11 C13 114.2(6) . . ?
N1 C11 H11 106.9 . . ?
C12 C11 H11 106.9 . . ?
C13 C11 H11 106.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 122.5(5) . . ?
C15 C14 N1 133.0(6) . . ?
C19 C14 N1 104.4(6) . . ?
C14 C15 C16 116.6(7) . . ?
C14 C15 H15 121.7 . . ?
C16 C15 H15 121.7 . . ?
C17 C16 C15 120.7(7) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 123.3(6) . . ?
C18 C17 H17 118.4 . . ?
C16 C17 H17 118.4 . . ?
C17 C18 C19 117.0(7) . . ?
C17 C18 H18 121.5 . . ?
C19 C18 H18 121.5 . . ?
C14 C19 N2 107.0(5) . . ?
C14 C19 C18 119.8(7) . . ?
N2 C19 C18 133.2(7) . . ?
N2 C20 C22 111.7(5) . . ?
N2 C20 C21 108.9(6) . . ?
C22 C20 C21 114.3(5) . . ?
N2 C20 H20 107.2 . . ?
C22 C20 H20 107.2 . . ?
C21 C20 H20 107.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N4 C23 N3 105.9(5) . . ?
N4 C23 Cu2 128.7(4) . . ?
N3 C23 Cu2 125.4(4) . . ?
N3 C24 C25 111.8(4) . . ?
N3 C24 C26 111.3(5) . . ?
C25 C24 C26 112.7(5) . . ?
N3 C24 H24 106.8 . . ?
C25 C24 H24 106.8 . . ?
C26 C24 H24 106.8 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 C27 N3 106.7(5) . . ?
C32 C27 C28 120.5(6) . . ?
N3 C27 C28 132.7(5) . . ?
C29 C28 C27 117.5(6) . . ?
C29 C28 H28 121.2 . . ?
C27 C28 H28 121.2 . . ?
C28 C29 C30 122.6(7) . . ?
C28 C29 H29 118.7 . . ?
C30 C29 H29 118.7 . . ?
C31 C30 C29 120.3(7) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 117.6(6) . . ?
C30 C31 H31 121.2 . . ?
C32 C31 H31 121.2 . . ?
C27 C32 N4 106.0(5) . . ?
C27 C32 C31 121.5(6) . . ?
N4 C32 C31 132.5(5) . . ?
N4 C33 C35 112.5(4) . . ?
N4 C33 C34 110.3(5) . . ?
C35 C33 C34 113.3(5) . . ?
N4 C33 H33 106.7 . . ?
C35 C33 H33 106.7 . . ?
C34 C33 H33 106.7 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C10 N1 C14 112.4(5) . . ?
C10 N1 C11 123.3(5) . . ?
C14 N1 C11 124.3(5) . . ?
C10 N2 C19 111.3(5) . . ?
C10 N2 C20 122.7(5) . . ?
C19 N2 C20 126.0(5) . . ?
C23 N3 C27 110.4(4) . . ?
C23 N3 C24 122.9(5) . . ?
C27 N3 C24 126.7(5) . . ?
C23 N4 C32 110.9(4) . . ?
C23 N4 C33 122.4(4) . . ?
C32 N4 C33 126.7(5) . . ?
C1 Fe1 C3 94.0(3) . . ?
C1 Fe1 C2 94.3(2) . . ?
C3 Fe1 C2 99.9(2) . . ?
C1 Fe1 Se1 93.86(19) . . ?
C3 Fe1 Se1 139.70(18) . . ?
C2 Fe1 Se1 118.83(18) . . ?
C1 Fe1 Cu2 154.0(2) . . ?
C3 Fe1 Cu2 62.46(17) . . ?
C2 Fe1 Cu2 80.20(17) . . ?
Se1 Fe1 Cu2 111.12(4) . . ?
C1 Fe1 Cu1 116.7(2) . . ?
C3 Fe1 Cu1 143.99(18) . . ?
C2 Fe1 Cu1 61.69(17) . . ?
Se1 Fe1 Cu1 60.68(4) . . ?
Cu2 Fe1 Cu1 83.14(4) . . ?
C1 Fe1 Fe3 98.92(19) . . ?
C3 Fe1 Fe3 84.34(18) . . ?
C2 Fe1 Fe3 165.83(17) . . ?
Se1 Fe1 Fe3 55.39(3) . . ?
Cu2 Fe1 Fe3 89.98(5) . . ?
Cu1 Fe1 Fe3 107.24(4) . . ?
C1 Fe1 Fe2 147.32(19) . . ?
C3 Fe1 Fe2 105.90(18) . . ?
C2 Fe1 Fe2 107.13(17) . . ?
Se1 Fe1 Fe2 54.34(3) . . ?
Cu2 Fe1 Fe2 56.79(4) . . ?
Cu1 Fe1 Fe2 57.76(3) . . ?
Fe3 Fe1 Fe2 58.73(4) . . ?
C5 Fe2 C4 100.5(3) . . ?
C5 Fe2 C6 94.2(3) . . ?
C4 Fe2 C6 94.3(3) . . ?
C5 Fe2 Se1 135.2(2) . . ?
C4 Fe2 Se1 123.21(19) . . ?
C6 Fe2 Se1 91.8(2) . . ?
C5 Fe2 Cu2 67.8(2) . . ?
C4 Fe2 Cu2 74.93(19) . . ?
C6 Fe2 Cu2 156.3(2) . . ?
Se1 Fe2 Cu2 111.78(4) . . ?
C5 Fe2 Cu1 150.9(2) . . ?
C4 Fe2 Cu1 63.90(19) . . ?
C6 Fe2 Cu1 110.6(2) . . ?
Se1 Fe2 Cu1 61.17(4) . . ?
Cu2 Fe2 Cu1 84.03(4) . . ?
C5 Fe2 Fe3 80.0(2) . . ?
C4 Fe2 Fe3 163.57(18) . . ?
C6 Fe2 Fe3 102.01(19) . . ?
Se1 Fe2 Fe3 55.42(3) . . ?
Cu2 Fe2 Fe3 90.31(4) . . ?
Cu1 Fe2 Fe3 108.09(4) . . ?
C5 Fe2 Fe1 107.69(18) . . ?
C4 Fe2 Fe1 106.19(18) . . ?
C6 Fe2 Fe1 146.2(2) . . ?
Se1 Fe2 Fe1 54.45(4) . . ?
Cu2 Fe2 Fe1 57.33(3) . . ?
Cu1 Fe2 Fe1 58.79(4) . . ?
Fe3 Fe2 Fe1 58.72(3) . . ?
C9 Fe3 C7 96.6(3) . . ?
C9 Fe3 C8 99.2(3) . . ?
C7 Fe3 C8 97.6(3) . . ?
C9 Fe3 Se1 97.47(18) . . ?
C7 Fe3 Se1 156.65(19) . . ?
C8 Fe3 Se1 98.4(2) . . ?
C9 Fe3 Fe1 96.07(19) . . ?
C7 Fe3 Fe1 103.90(19) . . ?
C8 Fe3 Fe1 151.92(19) . . ?
Se1 Fe3 Fe1 56.13(3) . . ?
C9 Fe3 Fe2 151.87(18) . . ?
C7 Fe3 Fe2 105.83(19) . . ?
C8 Fe3 Fe2 94.47(19) . . ?
Se1 Fe3 Fe2 56.04(3) . . ?
Fe1 Fe3 Fe2 62.55(4) . . ?
C10 Cu1 C2 112.0(2) . . ?
C10 Cu1 C4 118.4(2) . . ?
C2 Cu1 C4 104.00(19) . . ?
C10 Cu1 Se1 128.3(2) . . ?
C2 Cu1 Se1 94.20(14) . . ?
C4 Cu1 Se1 95.33(15) . . ?
C10 Cu1 Fe2 150.45(16) . . ?
C2 Cu1 Fe2 96.13(14) . . ?
C4 Cu1 Fe2 41.66(15) . . ?
Se1 Cu1 Fe2 54.74(3) . . ?
C10 Cu1 Fe1 145.52(16) . . ?
C2 Cu1 Fe1 41.91(14) . . ?
C4 Cu1 Fe1 93.35(14) . . ?
Se1 Cu1 Fe1 54.46(3) . . ?
Fe2 Cu1 Fe1 63.45(3) . . ?
C23 Cu2 C3 111.9(2) . . ?
C23 Cu2 C5 115.0(2) . . ?
C3 Cu2 C5 103.9(2) . . ?
C23 Cu2 Fe2 147.28(15) . . ?
C3 Cu2 Fe2 98.12(15) . . ?
C5 Cu2 Fe2 41.68(17) . . ?
C23 Cu2 Fe1 146.59(15) . . ?
C3 Cu2 Fe1 42.83(15) . . ?
C5 Cu2 Fe1 95.19(17) . . ?
Fe2 Cu2 Fe1 65.88(4) . . ?
Fe3 Se1 Fe2 68.55(4) . . ?
Fe3 Se1 Fe1 68.48(4) . . ?
Fe2 Se1 Fe1 71.20(4) . . ?
Fe3 Se1 Cu1 121.21(4) . . ?
Fe2 Se1 Cu1 64.09(4) . . ?
Fe1 Se1 Cu1 64.85(3) . . ?

_refine_diff_density_max         0.711
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.109

