# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

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

data_Probe_4
_database_code_depnum_ccdc_archive 'CCDC 2156613'
loop_
_audit_author_name
_audit_author_address
'Ray J. Butcher'
;Department of Chemistry, Howard University, Washington
United States of America
;
_audit_update_record             
;
2022-03-05 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 O3 Se, H2 O'
_chemical_formula_sum            'C16 H14 O4 Se'
_chemical_formula_weight         349.23

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'
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                   10.3926(7)
_cell_length_b                   11.6371(7)
_cell_length_c                   11.9617(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.690(4)
_cell_angle_gamma                90
_cell_volume                     1446.02(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6038
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.85

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    2.609
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4348
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            17974
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.628
_diffrn_reflns_theta_max         29.655
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4066
_reflns_number_gt                2849
_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    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_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)+(0.0554P)²+0.6812P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4066
_refine_ls_number_parameters     200
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.68220(3) 0.45496(3) 0.07573(3) 0.02314(12) Uani 1 1 d . . . . .
O1 O 0.8546(2) 0.67335(16) 0.42974(16) 0.0186(5) Uani 1 1 d . . . . .
O2 O 0.8814(2) 0.84200(18) 0.35126(19) 0.0264(5) Uani 1 1 d . . . . .
O3 O 0.8259(3) 0.31828(18) 0.62210(18) 0.0259(5) Uani 1 1 d . . . . .
H3O H 0.808825 0.362391 0.675235 0.082(19) Uiso 1 1 calc R . . . .
O1W O 0.7797(4) 0.4491(2) 0.7962(2) 0.0463(8) Uani 1 1 d D . . . .
H1W1 H 0.811(5) 0.511(2) 0.810(4) 0.061(16) Uiso 1 1 d D . . . .
H1W2 H 0.736(5) 0.433(4) 0.849(3) 0.066(17) Uiso 1 1 d D . . . .
C1 C 0.8712(3) 0.7389(3) 0.3356(2) 0.0202(6) Uani 1 1 d . . . . .
C2 C 0.8725(3) 0.6808(2) 0.2300(2) 0.0201(6) Uani 1 1 d . . . . .
H2A H 0.877928 0.725054 0.163571 0.024 Uiso 1 1 calc R U . . .
C3 C 0.8662(3) 0.5644(2) 0.2218(3) 0.0180(6) Uani 1 1 d . . . . .
C4 C 0.8595(3) 0.4970(3) 0.3227(2) 0.0167(6) Uani 1 1 d . . . . .
C5 C 0.8617(3) 0.3762(2) 0.3279(2) 0.0194(6) Uani 1 1 d . . . . .
H5A H 0.869774 0.333395 0.260850 0.023 Uiso 1 1 calc R U . . .
C6 C 0.8525(3) 0.3188(2) 0.4273(2) 0.0210(7) Uani 1 1 d . . . . .
H6A H 0.856662 0.237293 0.428910 0.025 Uiso 1 1 calc R U . . .
C7 C 0.8368(3) 0.3806(2) 0.5269(2) 0.0188(6) Uani 1 1 d . . . . .
C8 C 0.8354(3) 0.5002(3) 0.5260(2) 0.0191(6) Uani 1 1 d . . . . .
H8A H 0.824872 0.542665 0.592930 0.023 Uiso 1 1 calc R U . . .
C9 C 0.8496(3) 0.5553(2) 0.4249(2) 0.0174(6) Uani 1 1 d . . . . .
C10 C 0.8604(3) 0.5083(3) 0.1097(2) 0.0205(6) Uani 1 1 d . . . . .
H10A H 0.920285 0.442096 0.109222 0.025 Uiso 1 1 calc R U . . .
H10B H 0.887051 0.563576 0.051931 0.025 Uiso 1 1 calc R U . . .
C11 C 0.5994(3) 0.6026(3) 0.0898(3) 0.0249(7) Uani 1 1 d . . . . .
C12 C 0.5363(4) 0.6283(3) 0.1871(3) 0.0350(8) Uani 1 1 d . . . . .
H12A H 0.533309 0.573383 0.245717 0.042 Uiso 1 1 calc R U . . .
C13 C 0.4775(4) 0.7342(4) 0.1985(3) 0.0402(9) Uani 1 1 d . . . . .
H13A H 0.433781 0.751614 0.265057 0.048 Uiso 1 1 calc R U . . .
C14 C 0.4818(4) 0.8147(3) 0.1142(4) 0.0404(9) Uani 1 1 d . . . . .
H14A H 0.441760 0.887437 0.123020 0.048 Uiso 1 1 calc R U . . .
C15 C 0.5445(4) 0.7896(3) 0.0165(4) 0.0409(9) Uani 1 1 d . . . . .
H15A H 0.547621 0.844702 -0.041939 0.049 Uiso 1 1 calc R U . . .
C16 C 0.6029(4) 0.6826(3) 0.0047(3) 0.0308(8) Uani 1 1 d . . . . .
H16A H 0.645346 0.664621 -0.062321 0.037 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 C11 1.931(3) . ?
Se1 C10 1.984(3) . ?
O1 C1 1.375(3) . ?
O1 C9 1.375(3) . ?
O2 C1 1.219(4) . ?
O3 C7 1.358(3) . ?
O3 H3O 0.8400 . ?
O1W H1W1 0.808(18) . ?
O1W H1W2 0.811(19) . ?
C1 C2 1.433(4) . ?
C2 C3 1.359(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.443(4) . ?
C3 C10 1.491(4) . ?
C4 C9 1.404(4) . ?
C4 C5 1.408(4) . ?
C5 C6 1.369(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.404(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.392(4) . ?
C8 C9 1.381(4) . ?
C8 H8A 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.380(5) . ?
C11 C12 1.385(5) . ?
C12 C13 1.385(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.378(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.386(6) . ?
C14 H14A 0.9500 . ?
C15 C16 1.394(5) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 Se1 C10 96.88(13) . . ?
C1 O1 C9 121.6(2) . . ?
C7 O3 H3O 109.5 . . ?
H1W1 O1W H1W2 107(3) . . ?
O2 C1 O1 115.6(3) . . ?
O2 C1 C2 126.7(3) . . ?
O1 C1 C2 117.7(2) . . ?
C3 C2 C1 122.2(3) . . ?
C3 C2 H2A 118.9 . . ?
C1 C2 H2A 118.9 . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 C10 120.2(3) . . ?
C4 C3 C10 120.8(3) . . ?
C9 C4 C5 116.5(3) . . ?
C9 C4 C3 118.2(3) . . ?
C5 C4 C3 125.4(3) . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5A 119.2 . . ?
C4 C5 H5A 119.2 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6A 120.0 . . ?
C7 C6 H6A 120.0 . . ?
O3 C7 C8 122.6(3) . . ?
O3 C7 C6 116.9(2) . . ?
C8 C7 C6 120.4(3) . . ?
C9 C8 C7 118.0(3) . . ?
C9 C8 H8A 121.0 . . ?
C7 C8 H8A 121.0 . . ?
O1 C9 C8 115.6(3) . . ?
O1 C9 C4 121.0(3) . . ?
C8 C9 C4 123.4(3) . . ?
C3 C10 Se1 109.5(2) . . ?
C3 C10 H10A 109.8 . . ?
Se1 C10 H10A 109.8 . . ?
C3 C10 H10B 109.8 . . ?
Se1 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C16 C11 C12 119.8(3) . . ?
C16 C11 Se1 121.0(3) . . ?
C12 C11 Se1 119.2(3) . . ?
C13 C12 C11 119.7(4) . . ?
C13 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
C14 C13 C12 120.6(4) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C14 C15 C16 119.4(4) . . ?
C14 C15 H15A 120.3 . . ?
C16 C15 H15A 120.3 . . ?
C11 C16 C15 120.5(4) . . ?
C11 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 O2 -176.0(3) . . . . ?
C9 O1 C1 C2 5.1(4) . . . . ?
O2 C1 C2 C3 177.0(3) . . . . ?
O1 C1 C2 C3 -4.3(5) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C1 C2 C3 C10 176.6(3) . . . . ?
C2 C3 C4 C9 4.9(4) . . . . ?
C10 C3 C4 C9 -172.4(3) . . . . ?
C2 C3 C4 C5 -175.3(3) . . . . ?
C10 C3 C4 C5 7.4(5) . . . . ?
C9 C4 C5 C6 1.1(5) . . . . ?
C3 C4 C5 C6 -178.8(3) . . . . ?
C4 C5 C6 C7 1.8(5) . . . . ?
C5 C6 C7 O3 178.8(3) . . . . ?
C5 C6 C7 C8 -2.4(5) . . . . ?
O3 C7 C8 C9 178.8(3) . . . . ?
C6 C7 C8 C9 0.0(5) . . . . ?
C1 O1 C9 C8 178.6(3) . . . . ?
C1 O1 C9 C4 -1.0(4) . . . . ?
C7 C8 C9 O1 -176.6(3) . . . . ?
C7 C8 C9 C4 3.0(5) . . . . ?
C5 C4 C9 O1 176.0(3) . . . . ?
C3 C4 C9 O1 -4.2(4) . . . . ?
C5 C4 C9 C8 -3.6(5) . . . . ?
C3 C4 C9 C8 176.3(3) . . . . ?
C2 C3 C10 Se1 -104.3(3) . . . . ?
C4 C3 C10 Se1 73.0(3) . . . . ?
C16 C11 C12 C13 -0.2(6) . . . . ?
Se1 C11 C12 C13 179.4(3) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C12 C13 C14 C15 0.5(6) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
C12 C11 C16 C15 0.7(5) . . . . ?
Se1 C11 C16 C15 -179.0(3) . . . . ?
C14 C15 C16 C11 -0.5(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3O O1W 0.84 1.80 2.635(3) 175.4 . yes
O1W H1W1 O2 0.808(18) 1.92(2) 2.724(3) 176(5) 4_576 yes
O1W H1W2 Se1 0.811(19) 2.80(3) 3.523(3) 150(4) 1_556 yes
C10 H10A O2 0.99 2.40 3.329(4) 155.7 2_745 yes
C10 H10B O2 0.99 2.64 3.561(4) 155.1 4_575 yes

_refine_diff_density_max         1.114
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.126



####################################################################### 
# 
# 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_Probe_5
_database_code_depnum_ccdc_archive 'CCDC 2156614'
loop_
_audit_author_name
_audit_author_address
'Ray J. Butcher'
;Department of Chemistry, Howard University, Washington
United States of America
;
_audit_update_record             
;
2022-03-05 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 O4.08 Se'
_chemical_formula_sum            'C18 H14 O4.08 Se'
_chemical_formula_weight         374.54

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'
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                   7.6073(5)
_cell_length_b                   9.4274(9)
_cell_length_c                   12.1570(11)
_cell_angle_alpha                106.478(3)
_cell_angle_beta                 104.683(2)
_cell_angle_gamma                103.015(2)
_cell_volume                     766.15(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      32.49

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_F_000             377
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    2.469
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6314
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            5560
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.378
_diffrn_reflns_theta_max         32.563
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5560
_reflns_number_gt                4814
_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    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_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)+(0.0224P)²+0.3178P] 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         5560
_refine_ls_number_parameters     220
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0669
_refine_ls_wR_factor_gt          0.0639
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
Se Se 0.27739(2) 0.06836(2) 0.62935(2) 0.01977(5) Uani 1 1 d . . . . .
O1 O 0.58863(17) 0.28051(15) 0.29590(10) 0.0280(2) Uani 1 1 d . . . . .
O2 O 0.76387(14) 0.39925(12) 0.49129(9) 0.0197(2) Uani 1 1 d . . . . .
O3 O 1.29187(16) 0.48803(13) 0.87663(10) 0.0236(2) Uani 1 1 d . . . . .
C1 C 0.43891(19) 0.31029(16) 0.55669(13) 0.0165(2) Uani 1 1 d . . . . .
C2 C 0.4252(2) 0.26958(17) 0.43779(13) 0.0192(3) Uani 1 1 d . . . . .
H2A H 0.303427 0.210496 0.376902 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5895(2) 0.31278(17) 0.39990(13) 0.0203(3) Uani 1 1 d . . . . .
O4 O 1.16696(14) 0.68533(12) 0.90185(9) 0.0205(2) Uani 1 1 d . . . . .
C4 C 0.7815(2) 0.44482(16) 0.61296(12) 0.0162(2) Uani 1 1 d . . . . .
C5 C 0.9639(2) 0.53509(16) 0.69465(13) 0.0181(3) Uani 1 1 d . . . . .
H5A H 1.068499 0.562280 0.667101 0.022 Uiso 1 1 calc R U . . .
C6 C 0.98798(19) 0.58396(16) 0.81744(13) 0.0177(2) Uani 1 1 d . . . . .
C7 C 0.8373(2) 0.54747(16) 0.86036(13) 0.0187(3) Uani 1 1 d . U . . .
H7A H 0.858086 0.583169 0.945385 0.022 Uiso 0.919(4) 1 calc R U P A 1
C8 C 0.6562(2) 0.45813(16) 0.77697(13) 0.0177(2) Uani 1 1 d . . . . .
H8A H 0.552153 0.433115 0.805379 0.021 Uiso 1 1 calc R U . . .
C9 C 0.62398(19) 0.40380(15) 0.65072(12) 0.0157(2) Uani 1 1 d . . . . .
C10 C 1.3150(2) 0.62501(17) 0.91991(12) 0.0180(3) Uani 1 1 d . . . . .
C11 C 1.5001(2) 0.75170(19) 0.99854(14) 0.0242(3) Uani 1 1 d . . . . .
H11A H 1.593594 0.706109 1.033606 0.036 Uiso 1 1 calc R U . . .
H11B H 1.478656 0.826354 1.064359 0.036 Uiso 1 1 calc R U . . .
H11C H 1.549341 0.805683 0.949202 0.036 Uiso 1 1 calc R U . . .
C12 C 0.2645(2) 0.25596(16) 0.58938(13) 0.0183(3) Uani 1 1 d . . . . .
H12A H 0.146422 0.230171 0.519908 0.022 Uiso 1 1 calc R U . . .
H12B H 0.263323 0.338844 0.660369 0.022 Uiso 1 1 calc R U . . .
C13 C 0.09781(19) 0.05895(16) 0.71465(12) 0.0170(2) Uani 1 1 d . . . . .
C14 C 0.1017(2) -0.03798(16) 0.78337(13) 0.0187(3) Uani 1 1 d . . . . .
H14A H 0.189322 -0.095641 0.785523 0.022 Uiso 1 1 calc R U . . .
C15 C -0.0240(2) -0.04873(17) 0.84834(13) 0.0215(3) Uani 1 1 d . . . . .
H15A H -0.022342 -0.114596 0.894737 0.026 Uiso 1 1 calc R U . . .
C16 C -0.1521(2) 0.03561(17) 0.84625(14) 0.0235(3) Uani 1 1 d . . . . .
H16A H -0.236223 0.028629 0.891862 0.028 Uiso 1 1 calc R U . . .
C17 C -0.1564(2) 0.13003(17) 0.77717(15) 0.0234(3) Uani 1 1 d . . . . .
H17A H -0.244412 0.187342 0.775210 0.028 Uiso 1 1 calc R U . . .
C18 C -0.0327(2) 0.14159(17) 0.71056(14) 0.0208(3) Uani 1 1 d . . . . .
H18A H -0.037433 0.205501 0.662613 0.025 Uiso 1 1 calc R U . . .
O1A O 0.8971(15) 0.6110(12) 0.9882(9) 0.009(3) Uani 0.081(4) 1 d . U P A 2
H1A H 0.894292 0.538877 1.016038 0.014 Uiso 0.081(4) 1 calc R U P A 2


_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
Se C13 1.9145(14) . ?
Se C12 1.9787(14) . ?
O1 C3 1.2115(18) . ?
O2 C4 1.3796(16) . ?
O2 C3 1.3822(17) . ?
O3 C10 1.2004(18) . ?
C1 C2 1.3559(19) . ?
C1 C9 1.4558(19) . ?
C1 C12 1.5022(19) . ?
C2 C3 1.452(2) . ?
C2 H2A 0.9500 . ?
O4 C10 1.3686(17) . ?
O4 C6 1.4034(17) . ?
C4 C5 1.3880(19) . ?
C4 C9 1.4025(18) . ?
C5 C6 1.381(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.3900(19) . ?
C7 C8 1.385(2) . ?
C7 O1A 1.404(10) . ?
C7 H7A 0.9500 . ?
C8 C9 1.4088(19) . ?
C8 H8A 0.9500 . ?
C10 C11 1.495(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.393(2) . ?
C13 C14 1.4024(19) . ?
C14 C15 1.391(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.389(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.386(2) . ?
C16 H16A 0.9500 . ?
C17 C18 1.394(2) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
O1A H1A 0.8400 . ?

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
C13 Se C12 100.03(6) . . ?
C4 O2 C3 121.84(11) . . ?
C2 C1 C9 119.20(12) . . ?
C2 C1 C12 119.68(13) . . ?
C9 C1 C12 121.10(12) . . ?
C1 C2 C3 122.55(13) . . ?
C1 C2 H2A 118.7 . . ?
C3 C2 H2A 118.7 . . ?
O1 C3 O2 116.76(13) . . ?
O1 C3 C2 126.34(14) . . ?
O2 C3 C2 116.90(12) . . ?
C10 O4 C6 117.42(11) . . ?
O2 C4 C5 115.64(12) . . ?
O2 C4 C9 121.80(12) . . ?
C5 C4 C9 122.55(13) . . ?
C6 C5 C4 117.60(12) . . ?
C6 C5 H5A 121.2 . . ?
C4 C5 H5A 121.2 . . ?
C5 C6 C7 122.48(13) . . ?
C5 C6 O4 118.97(12) . . ?
C7 C6 O4 118.31(13) . . ?
C8 C7 C6 118.84(13) . . ?
C8 C7 O1A 129.3(5) . . ?
C6 C7 O1A 111.9(5) . . ?
C8 C7 H7A 120.6 . . ?
C6 C7 H7A 120.6 . . ?
C7 C8 C9 121.06(13) . . ?
C7 C8 H8A 119.5 . . ?
C9 C8 H8A 119.5 . . ?
C4 C9 C8 117.47(12) . . ?
C4 C9 C1 117.68(12) . . ?
C8 C9 C1 124.84(12) . . ?
O3 C10 O4 122.45(13) . . ?
O3 C10 C11 126.88(14) . . ?
O4 C10 C11 110.67(12) . . ?
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 . . ?
C1 C12 Se 107.13(9) . . ?
C1 C12 H12A 110.3 . . ?
Se C12 H12A 110.3 . . ?
C1 C12 H12B 110.3 . . ?
Se C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
C18 C13 C14 120.09(13) . . ?
C18 C13 Se 123.43(11) . . ?
C14 C13 Se 116.48(11) . . ?
C15 C14 C13 119.25(13) . . ?
C15 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
C16 C15 C14 120.85(14) . . ?
C16 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
C17 C16 C15 119.56(14) . . ?
C17 C16 H16A 120.2 . . ?
C15 C16 H16A 120.2 . . ?
C16 C17 C18 120.56(14) . . ?
C16 C17 H17A 119.7 . . ?
C18 C17 H17A 119.7 . . ?
C13 C18 C17 119.68(13) . . ?
C13 C18 H18A 120.2 . . ?
C17 C18 H18A 120.2 . . ?
C7 O1A H1A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C3 1.4(2) . . . . ?
C12 C1 C2 C3 -177.49(13) . . . . ?
C4 O2 C3 O1 178.98(13) . . . . ?
C4 O2 C3 C2 -1.0(2) . . . . ?
C1 C2 C3 O1 179.80(15) . . . . ?
C1 C2 C3 O2 -0.3(2) . . . . ?
C3 O2 C4 C5 -178.15(12) . . . . ?
C3 O2 C4 C9 1.0(2) . . . . ?
O2 C4 C5 C6 179.70(12) . . . . ?
C9 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C7 -0.7(2) . . . . ?
C4 C5 C6 O4 -175.09(12) . . . . ?
C10 O4 C6 C5 -71.44(17) . . . . ?
C10 O4 C6 C7 113.98(14) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
O4 C6 C7 C8 174.68(12) . . . . ?
C5 C6 C7 O1A -179.6(5) . . . . ?
O4 C6 C7 O1A -5.2(5) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
O1A C7 C8 C9 -179.7(6) . . . . ?
O2 C4 C9 C8 -179.01(12) . . . . ?
C5 C4 C9 C8 0.1(2) . . . . ?
O2 C4 C9 C1 0.10(19) . . . . ?
C5 C4 C9 C1 179.23(13) . . . . ?
C7 C8 C9 C4 -0.6(2) . . . . ?
C7 C8 C9 C1 -179.63(13) . . . . ?
C2 C1 C9 C4 -1.27(19) . . . . ?
C12 C1 C9 C4 177.56(12) . . . . ?
C2 C1 C9 C8 177.77(13) . . . . ?
C12 C1 C9 C8 -3.4(2) . . . . ?
C6 O4 C10 O3 -7.9(2) . . . . ?
C6 O4 C10 C11 172.14(12) . . . . ?
C2 C1 C12 Se 97.72(13) . . . . ?
C9 C1 C12 Se -81.12(14) . . . . ?
C18 C13 C14 C15 -0.9(2) . . . . ?
Se C13 C14 C15 179.42(11) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C15 C16 C17 0.9(2) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C14 C13 C18 C17 1.4(2) . . . . ?
Se C13 C18 C17 -178.93(11) . . . . ?
C16 C17 C18 C13 -0.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5A O1 0.95 2.55 3.4123(18) 151.5 2_766 yes
C5 H5A O2 0.95 2.63 3.5171(17) 156.3 2_766 yes
C8 H8A O3 0.95 2.45 3.3302(18) 153.6 1_455 yes
C11 H11A O3 0.98 2.58 3.501(2) 156.0 2_867 yes
C12 H12B O3 0.99 2.53 3.4810(18) 160.4 1_455 yes
O1A^b H1A^b O3 0.84 2.18 2.665(11) 117.0 2_767 yes
O1A^b H1A^b O4 0.84 2.58 3.416(11) 171.4 2_767 yes
O1A^b H1A^b O1A^b 0.84 2.35 2.92(2) 125.1 2_767 yes

_refine_diff_density_max         0.540
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.074



