# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

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

data_pf35
_database_code_depnum_ccdc_archive 'CCDC 1829710'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 O4 Se2 Zn'
_chemical_formula_weight         441.49

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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/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                   7.6565(3)
_cell_length_b                   23.8778(11)
_cell_length_c                   7.4531(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.8542(16)
_cell_angle_gamma                90
_cell_volume                     1361.87(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.153
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.101
_exptl_absorpt_coefficient_mu    7.153
_shelx_estimated_absorpt_T_min   0.160
_shelx_estimated_absorpt_T_max   0.532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.104
_exptl_absorpt_correction_T_max  0.345
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14978
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.662
_diffrn_reflns_theta_max         28.295
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3370
_reflns_number_gt                2982
_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0198P)²+0.8932P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3370
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0222
_refine_ls_wR_factor_ref         0.0502
_refine_ls_wR_factor_gt          0.0477
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
Zn1 Zn 0.25204(3) 0.37590(2) 0.88777(3) 0.01797(7) Uani 1 1 d . . . . .
Se1 Se 0.11642(3) 0.44314(2) 0.68223(3) 0.01789(6) Uani 1 1 d . . . . .
Se2 Se 0.48754(3) 0.31249(2) 0.81752(3) 0.01935(6) Uani 1 1 d . . . . .
O1 O 0.3045(2) 0.43662(6) 1.0599(2) 0.0197(3) Uani 1 1 d . . . . .
O2 O 0.10643(19) 0.31191(6) 0.9590(2) 0.0193(3) Uani 1 1 d . . . . .
O3 O 0.2588(2) 0.58516(6) 1.0826(2) 0.0219(3) Uani 1 1 d . . . . .
O4 O 0.1213(2) 0.16258(6) 0.9178(2) 0.0221(3) Uani 1 1 d . . . . .
C1 C 0.2608(3) 0.48760(8) 1.0104(3) 0.0160(4) Uani 1 1 d . . . . .
C2 C 0.1738(3) 0.50048(8) 0.8436(3) 0.0165(4) Uani 1 1 d . . . . .
C3 C 0.1321(3) 0.55711(9) 0.8065(3) 0.0212(5) Uani 1 1 d . . . . .
H3 H 0.0736 0.5668 0.6965 0.025 Uiso 1 1 calc R U . . .
C4 C 0.1750(3) 0.59748(9) 0.9266(3) 0.0239(5) Uani 1 1 d . . . . .
H4 H 0.1453 0.6353 0.9002 0.029 Uiso 1 1 calc R U . . .
C5 C 0.2990(3) 0.53197(8) 1.1263(3) 0.0174(4) Uani 1 1 d . . . . .
C6 C 0.3824(3) 0.52552(9) 1.3070(3) 0.0240(5) Uani 1 1 d . . . . .
H6A H 0.4229 0.5621 1.3508 0.036 Uiso 1 1 calc R U . . .
H6B H 0.4822 0.5000 1.3003 0.036 Uiso 1 1 calc R U . . .
H6C H 0.2974 0.5102 1.3894 0.036 Uiso 1 1 calc R U . . .
C7 C 0.1687(3) 0.26184(8) 0.9248(3) 0.0161(4) Uani 1 1 d . . . . .
C8 C 0.3386(3) 0.25258(8) 0.8557(3) 0.0159(4) Uani 1 1 d . . . . .
C9 C 0.3888(3) 0.19705(9) 0.8200(3) 0.0202(4) Uani 1 1 d . . . . .
H9 H 0.5006 0.1898 0.7736 0.024 Uiso 1 1 calc R U . . .
C10 C 0.2796(3) 0.15400(9) 0.8511(3) 0.0233(5) Uani 1 1 d . . . . .
H10 H 0.3156 0.1169 0.8252 0.028 Uiso 1 1 calc R U . . .
C11 C 0.0649(3) 0.21507(8) 0.9551(3) 0.0190(4) Uani 1 1 d . . . . .
C12 C -0.1109(3) 0.21606(10) 1.0319(3) 0.0261(5) Uani 1 1 d . . . . .
H12A H -0.1710 0.1807 1.0047 0.039 Uiso 1 1 calc R U . . .
H12B H -0.1785 0.2472 0.9796 0.039 Uiso 1 1 calc R U . . .
H12C H -0.0996 0.2209 1.1623 0.039 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
Zn1 O1 1.9686(15) . ?
Zn1 O2 1.9741(14) . ?
Zn1 Se2 2.4246(3) . ?
Zn1 Se1 2.4289(3) . ?
Se1 C2 1.866(2) . ?
Se2 C8 1.857(2) . ?
O1 C1 1.312(2) . ?
O2 C7 1.315(2) . ?
O3 C4 1.343(3) . ?
O3 C5 1.344(3) . ?
O4 C10 1.341(3) . ?
O4 C11 1.357(3) . ?
C1 C5 1.392(3) . ?
C1 C2 1.425(3) . ?
C2 C3 1.414(3) . ?
C3 C4 1.348(3) . ?
C5 C6 1.479(3) . ?
C7 C11 1.393(3) . ?
C7 C8 1.432(3) . ?
C8 C9 1.408(3) . ?
C9 C10 1.350(3) . ?
C11 C12 1.480(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O2 120.00(6) . . ?
O1 Zn1 Se2 117.58(5) . . ?
O2 Zn1 Se2 90.30(4) . . ?
O1 Zn1 Se1 89.89(4) . . ?
O2 Zn1 Se1 116.58(5) . . ?
Se2 Zn1 Se1 125.612(13) . . ?
C2 Se1 Zn1 89.52(6) . . ?
C8 Se2 Zn1 89.05(6) . . ?
C1 O1 Zn1 117.09(13) . . ?
C7 O2 Zn1 116.10(13) . . ?
C4 O3 C5 121.08(17) . . ?
C10 O4 C11 120.96(17) . . ?
O1 C1 C5 119.01(19) . . ?
O1 C1 C2 123.59(18) . . ?
C5 C1 C2 117.39(18) . . ?
C3 C2 C1 118.22(19) . . ?
C3 C2 Se1 121.92(16) . . ?
C1 C2 Se1 119.85(15) . . ?
C4 C3 C2 120.4(2) . . ?
O3 C4 C3 121.14(19) . . ?
O3 C5 C1 121.78(19) . . ?
O3 C5 C6 114.05(18) . . ?
C1 C5 C6 124.16(19) . . ?
O2 C7 C11 119.0(2) . . ?
O2 C7 C8 123.33(18) . . ?
C11 C7 C8 117.66(19) . . ?
C9 C8 C7 118.02(19) . . ?
C9 C8 Se2 121.60(17) . . ?
C7 C8 Se2 120.38(15) . . ?
C10 C9 C8 120.7(2) . . ?
O4 C10 C9 121.30(19) . . ?
O4 C11 C7 121.3(2) . . ?
O4 C11 C12 113.15(18) . . ?
C7 C11 C12 125.5(2) . . ?

_refine_diff_density_max         0.486
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.096

_shelxl_version_number           2014-3

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

data_pf39
_database_code_depnum_ccdc_archive 'CCDC 1829712'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Ni O5 Se2'
_chemical_formula_weight         452.85

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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/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                   8.2986(6)
_cell_length_b                   24.7783(14)
_cell_length_c                   6.9641(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.042(3)
_cell_angle_gamma                90
_cell_volume                     1405.48(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5016
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      28.19

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.140
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    6.574
_shelx_estimated_absorpt_T_min   0.468
_shelx_estimated_absorpt_T_max   0.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.400
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15045
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_av_R_equivalents  0.0946
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.632
_diffrn_reflns_theta_max         28.295
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3482
_reflns_number_gt                2365
_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 SAINTPLUS'
_computing_data_reduction        'Bruker SAINTPLUS'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0154P)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_number_reflns         3482
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0628
_refine_ls_wR_factor_gt          0.0552
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.002

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 0.20862(5) 0.51221(2) 0.59849(6) 0.01644(11) Uani 1 1 d . . . . .
Se2 Se 0.02293(5) 0.62705(2) 0.43530(7) 0.01931(11) Uani 1 1 d . . . . .
Ni1 Ni 0.27743(6) 0.60119(2) 0.59395(8) 0.01438(13) Uani 1 1 d . . . . .
O2 O 0.7401(3) 0.47042(10) 0.8897(4) 0.0178(6) Uani 1 1 d . . . . .
O1 O 0.4932(3) 0.58512(10) 0.7194(4) 0.0175(6) Uani 1 1 d . . . . .
O3 O 0.3470(3) 0.67342(10) 0.6028(4) 0.0192(7) Uani 1 1 d . . . . .
O4 O 0.1811(3) 0.80537(10) 0.4919(4) 0.0194(7) Uani 1 1 d . . . . .
C1 C 0.5359(5) 0.53453(15) 0.7576(6) 0.0144(9) Uani 1 1 d . . . . .
C2 C 0.4222(4) 0.49203(15) 0.7138(5) 0.0133(8) Uani 1 1 d . . . . .
C3 C 0.4750(5) 0.43891(15) 0.7559(6) 0.0184(10) Uani 1 1 d . . . . .
H3 H 0.4005 0.4097 0.7243 0.022 Uiso 1 1 calc R U . . .
C4 C 0.6330(5) 0.42958(15) 0.8422(6) 0.0197(10) Uani 1 1 d . . . . .
H4 H 0.6690 0.3935 0.8697 0.024 Uiso 1 1 calc R U . . .
C5 C 0.6951(5) 0.52205(15) 0.8495(6) 0.0165(9) Uani 1 1 d . . . . .
C6 C 0.8283(5) 0.56123(15) 0.9113(6) 0.0227(10) Uani 1 1 d . . . . .
H6A H 0.8961 0.5495 1.0352 0.034 Uiso 1 1 calc R U . . .
H6B H 0.7812 0.5967 0.9288 0.034 Uiso 1 1 calc R U . . .
H6C H 0.8963 0.5636 0.8110 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2423(5) 0.71191(15) 0.5392(6) 0.0149(9) Uani 1 1 d . . . . .
C8 C 0.0766(5) 0.70034(15) 0.4546(6) 0.0156(9) Uani 1 1 d . . . . .
C9 C -0.0328(5) 0.74292(16) 0.3964(6) 0.0199(10) Uani 1 1 d . . . . .
H9 H -0.1450 0.7359 0.3430 0.024 Uiso 1 1 calc R U . . .
C10 C 0.0237(5) 0.79408(16) 0.4175(6) 0.0209(10) Uani 1 1 d . . . . .
H10 H -0.0506 0.8230 0.3783 0.025 Uiso 1 1 calc R U . . .
C11 C 0.2913(5) 0.76562(15) 0.5502(6) 0.0186(9) Uani 1 1 d . . . . .
C12 C 0.4607(5) 0.78618(16) 0.6192(7) 0.0289(11) Uani 1 1 d . . . . .
H12A H 0.4666 0.8050 0.7441 0.043 Uiso 1 1 calc R U . . .
H12B H 0.4894 0.8112 0.5221 0.043 Uiso 1 1 calc R U . . .
H12C H 0.5380 0.7559 0.6370 0.043 Uiso 1 1 calc R U . . .
O5 O 0.6940(4) 0.67687(14) 0.6121(6) 0.0438(10) Uani 1 1 d . . . . .
H1 H 0.595(6) 0.660(2) 0.633(8) 0.066 Uiso 1 1 d . U . . .
H2 H 0.758(6) 0.650(2) 0.584(8) 0.066 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
Se1 C2 1.869(4) . ?
Se1 Ni1 2.2791(6) . ?
Se2 C8 1.868(4) . ?
Se2 Ni1 2.2799(6) . ?
Ni1 O1 1.879(3) . ?
Ni1 O3 1.878(2) . ?
O2 C5 1.347(4) . ?
O2 C4 1.346(4) . ?
O1 C1 1.316(4) . ?
O3 C7 1.309(4) . ?
O4 C10 1.339(4) . ?
O4 C11 1.353(4) . ?
C1 C5 1.389(5) . ?
C1 C2 1.408(5) . ?
C2 C3 1.400(5) . ?
C3 C4 1.354(5) . ?
C5 C6 1.472(5) . ?
C7 C11 1.390(5) . ?
C7 C8 1.418(5) . ?
C8 C9 1.400(5) . ?
C9 C10 1.350(5) . ?
C11 C12 1.486(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Se1 Ni1 92.59(12) . . ?
C8 Se2 Ni1 93.01(12) . . ?
O1 Ni1 O3 85.81(11) . . ?
O1 Ni1 Se1 90.44(8) . . ?
O3 Ni1 Se1 176.10(8) . . ?
O1 Ni1 Se2 175.53(8) . . ?
O3 Ni1 Se2 89.92(8) . . ?
Se1 Ni1 Se2 93.86(2) . . ?
C5 O2 C4 121.3(3) . . ?
C1 O1 Ni1 119.4(2) . . ?
C7 O3 Ni1 120.2(2) . . ?
C10 O4 C11 121.2(3) . . ?
O1 C1 C5 120.0(3) . . ?
O1 C1 C2 121.7(3) . . ?
C5 C1 C2 118.2(3) . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 Se1 125.0(3) . . ?
C1 C2 Se1 115.7(3) . . ?
C4 C3 C2 119.4(4) . . ?
O2 C4 C3 121.3(4) . . ?
O2 C5 C1 120.6(3) . . ?
O2 C5 C6 113.8(3) . . ?
C1 C5 C6 125.7(4) . . ?
O3 C7 C11 120.7(3) . . ?
O3 C7 C8 121.4(3) . . ?
C11 C7 C8 117.8(3) . . ?
C9 C8 C7 119.4(4) . . ?
C9 C8 Se2 125.4(3) . . ?
C7 C8 Se2 115.2(3) . . ?
C10 C9 C8 119.0(4) . . ?
O4 C10 C9 122.1(4) . . ?
O4 C11 C7 120.4(3) . . ?
O4 C11 C12 113.0(3) . . ?
C7 C11 C12 126.5(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O4 0.95 2.61 3.536(5) 166.5 2_646
C10 H10 O5 0.95 2.53 3.209(5) 128.1 4_475
C12 H12C O5 0.98 2.37 3.335(5) 167.6 .
O5 H1 O1 0.95(5) 2.18(5) 2.997(4) 143(4) .
O5 H1 O3 0.95(5) 2.05(5) 2.869(4) 143(4) .
O5 H2 Se2 0.90(5) 2.67(5) 3.432(4) 144(4) 1_655

_refine_diff_density_max         0.848
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.163

_shelxl_version_number           2014-3

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

data_pf37
_database_code_depnum_ccdc_archive 'CCDC 1829711'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Cu O4 Se2'
_chemical_formula_weight         439.66

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'
O O 0.0106 0.0060 '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/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                   7.4765(3)
_cell_length_b                   13.1079(5)
_cell_length_c                   6.9501(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.9898(13)
_cell_angle_gamma                90
_cell_volume                     668.63(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5670
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      28.31

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.184
_exptl_crystal_F_000             422
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.083
_exptl_absorpt_coefficient_mu    7.081
_shelx_estimated_absorpt_T_min   0.279
_shelx_estimated_absorpt_T_max   0.591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.197
_exptl_absorpt_correction_T_max  0.418
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6801
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.775
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1663
_reflns_number_gt                1558
_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0197P)²+0.4825P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1663
_refine_ls_number_parameters     89
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0199
_refine_ls_wR_factor_ref         0.0499
_refine_ls_wR_factor_gt          0.0489
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.144
_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
Se1 Se 0.80611(3) 0.05250(2) 0.13325(3) 0.02913(8) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 0.0000 0.0000 0.02384(9) Uani 1 2 d S . P . .
O1 O 0.42974(19) 0.14037(10) -0.0164(2) 0.0277(3) Uani 1 1 d . . . . .
C1 C 0.5528(3) 0.21165(14) 0.0388(3) 0.0221(3) Uani 1 1 d . . . . .
C5 C 0.5000(2) 0.31364(14) 0.0263(3) 0.0227(4) Uani 1 1 d . . . . .
O2 O 0.62332(18) 0.38905(10) 0.0771(2) 0.0270(3) Uani 1 1 d . . . . .
C4 C 0.7996(3) 0.36761(17) 0.1400(3) 0.0292(4) Uani 1 1 d . . . . .
H4 H 0.8838 0.4221 0.1716 0.035 Uiso 1 1 calc R U . . .
C3 C 0.8611(3) 0.27075(16) 0.1600(3) 0.0272(4) Uani 1 1 d . . . . .
H3 H 0.9870 0.2577 0.2060 0.033 Uiso 1 1 calc R U . . .
C2 C 0.7383(3) 0.18874(14) 0.1124(3) 0.0224(4) Uani 1 1 d . . . . .
C6 C 0.3119(3) 0.35084(15) -0.0421(3) 0.0289(4) Uani 1 1 d . . . . .
H6A H 0.2891 0.4093 0.0378 0.043 Uiso 1 1 calc R U . . .
H6B H 0.2254 0.2961 -0.0296 0.043 Uiso 1 1 calc R U . . .
H6C H 0.2964 0.3717 -0.1797 0.043 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 C2 1.8544(18) . ?
Se1 Cu1 2.4002(2) . ?
Cu1 O1 1.9108(13) 3_655 ?
Cu1 O1 1.9108(13) . ?
Cu1 Se1 2.4002(2) 3_655 ?
O1 C1 1.316(2) . ?
C1 C5 1.392(3) . ?
C1 C2 1.416(3) . ?
C5 O2 1.352(2) . ?
C5 C6 1.479(3) . ?
O2 C4 1.337(2) . ?
C4 C3 1.348(3) . ?
C3 C2 1.411(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Se1 Cu1 91.12(6) . . ?
O1 Cu1 O1 180.0 3_655 . ?
O1 Cu1 Se1 88.74(4) 3_655 3_655 ?
O1 Cu1 Se1 91.26(4) . 3_655 ?
O1 Cu1 Se1 91.26(4) 3_655 . ?
O1 Cu1 Se1 88.74(4) . . ?
Se1 Cu1 Se1 180.0 3_655 . ?
C1 O1 Cu1 119.81(12) . . ?
O1 C1 C5 119.30(17) . . ?
O1 C1 C2 122.48(17) . . ?
C5 C1 C2 118.23(17) . . ?
O2 C5 C1 120.98(16) . . ?
O2 C5 C6 113.72(16) . . ?
C1 C5 C6 125.30(17) . . ?
C4 O2 C5 120.82(16) . . ?
O2 C4 C3 121.82(18) . . ?
C4 C3 C2 119.95(18) . . ?
C3 C2 C1 118.14(17) . . ?
C3 C2 Se1 124.01(14) . . ?
C1 C2 Se1 117.83(14) . . ?

_refine_diff_density_max         0.600
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.081

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_pf40
_database_code_depnum_ccdc_archive 'CCDC 1829713'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 Fe O6 Se3'
_chemical_formula_weight         620.03

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'
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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c :H'
_space_group_name_Hall           'R 3 -2"c'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   14.8261(12)
_cell_length_b                   14.8261(12)
_cell_length_c                   16.0571(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3056.7(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8798
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      28.26

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_F_000             1794
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    6.130
_shelx_estimated_absorpt_T_min   0.377
_shelx_estimated_absorpt_T_max   0.515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.254
_exptl_absorpt_correction_T_max  0.347
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10165
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.748
_diffrn_reflns_theta_max         28.290
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             1651
_reflns_number_gt                1603
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_max     0.948
_reflns_Friedel_fraction_full    0.951

_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 SAINTPLUS'
_computing_data_reduction        'Bruker SAINTPLUS'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+0.4941P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 754 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.020(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1651
_refine_ls_number_parameters     86
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0195
_refine_ls_R_factor_gt           0.0185
_refine_ls_wR_factor_ref         0.0406
_refine_ls_wR_factor_gt          0.0404
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_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
Se1 Se 0.51900(2) 0.21227(2) 0.35952(2) 0.02688(10) Uani 1 1 d . . . . .
Fe2 Fe 0.6667 0.3333 0.25654(4) 0.01609(14) Uani 1 3 d S T P . .
O1 O 0.54296(15) 0.30050(15) 0.18675(13) 0.0178(4) Uani 1 1 d . . . . .
C1 C 0.4466(2) 0.2569(2) 0.21248(19) 0.0184(5) Uani 1 1 d . . . . .
C2 C 0.4174(2) 0.2160(2) 0.29466(19) 0.0211(6) Uani 1 1 d . . . . .
C4 C 0.2435(3) 0.1736(3) 0.2643(3) 0.0313(7) Uani 1 1 d . . . . .
H4 H 0.1737 0.1483 0.2820 0.038 Uiso 1 1 calc R U . . .
O2 O 0.26882(16) 0.20414(17) 0.18584(17) 0.0290(5) Uani 1 1 d . . . . .
C6 C 0.3788(3) 0.2677(3) 0.0689(2) 0.0300(7) Uani 1 1 d . . . . .
H6A H 0.3282 0.2059 0.0381 0.045 Uiso 1 1 calc R U . . .
H6B H 0.4494 0.2873 0.0508 0.045 Uiso 1 1 calc R U . . .
H6C H 0.3659 0.3253 0.0579 0.045 Uiso 1 1 calc R U . . .
C5 C 0.3681(2) 0.2447(2) 0.1587(2) 0.0224(6) Uani 1 1 d . . . . .
C3 C 0.3135(2) 0.1775(2) 0.3195(2) 0.0274(7) Uani 1 1 d . . . . .
H3 H 0.2929 0.1543 0.3751 0.033 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 C2 1.855(3) . ?
Se1 Fe2 2.6114(6) . ?
Fe2 O1 1.991(2) 2_655 ?
Fe2 O1 1.991(2) 3_665 ?
Fe2 O1 1.991(2) . ?
Fe2 Se1 2.6114(6) 2_655 ?
Fe2 Se1 2.6114(6) 3_665 ?
O1 C1 1.306(3) . ?
C1 C5 1.386(4) . ?
C1 C2 1.426(4) . ?
C2 C3 1.407(4) . ?
C4 O2 1.328(5) . ?
C4 C3 1.344(5) . ?
O2 C5 1.355(4) . ?
C6 C5 1.471(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Se1 Fe2 92.20(9) . . ?
O1 Fe2 O1 91.42(9) 2_655 3_665 ?
O1 Fe2 O1 91.42(9) 2_655 . ?
O1 Fe2 O1 91.42(9) 3_665 . ?
O1 Fe2 Se1 80.51(6) 2_655 2_655 ?
O1 Fe2 Se1 107.21(6) 3_665 2_655 ?
O1 Fe2 Se1 159.76(6) . 2_655 ?
O1 Fe2 Se1 159.76(6) 2_655 3_665 ?
O1 Fe2 Se1 80.51(6) 3_665 3_665 ?
O1 Fe2 Se1 107.21(6) . 3_665 ?
Se1 Fe2 Se1 84.18(2) 2_655 3_665 ?
O1 Fe2 Se1 107.21(6) 2_655 . ?
O1 Fe2 Se1 159.75(6) 3_665 . ?
O1 Fe2 Se1 80.51(6) . . ?
Se1 Fe2 Se1 84.18(2) 2_655 . ?
Se1 Fe2 Se1 84.18(2) 3_665 . ?
C1 O1 Fe2 126.09(19) . . ?
O1 C1 C5 120.4(3) . . ?
O1 C1 C2 121.8(3) . . ?
C5 C1 C2 117.7(3) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 Se1 124.7(2) . . ?
C1 C2 Se1 117.0(2) . . ?
O2 C4 C3 122.0(3) . . ?
C4 O2 C5 121.1(3) . . ?
O2 C5 C1 120.8(3) . . ?
O2 C5 C6 112.7(3) . . ?
C1 C5 C6 126.5(3) . . ?
C4 C3 C2 119.7(3) . . ?

_refine_diff_density_max         0.594
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.070

_shelxl_version_number           2014-3

