Synthesis, antioxidant and structural properties of modified ebselen derivatives and conjugates.
Doig, Adrian I.; Sands, Kai N.; Boongaling, Bienca; Zhou, Wen; Back, Thomas G.; Organic & biomolecular chemistry 22 (2024) 8881–8897; doi:10.1039/d4ob01400f

data_7160285
_publ_section_title
;
 Synthesis, antioxidant and structural properties of modified ebselen
 derivatives and conjugates.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8881
_journal_page_last               8897
_journal_paper_doi               10.1039/d4ob01400f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C20 H13 N2 O2 Se, C24 H20 P, 0.4(H2 O)'
_chemical_formula_sum            'C44 H33.8 N2 O2.4 P Se'
_chemical_formula_weight         738.86
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-05-29
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-29 deposited with the CCDC.	2024-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.4720(10)
_cell_angle_beta                 90.4550(10)
_cell_angle_gamma                103.3810(10)
_cell_formula_units_Z            4
_cell_length_a                   13.1170(5)
_cell_length_b                   16.3872(7)
_cell_length_c                   16.8435(7)
_cell_measurement_reflns_used    8764
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      27.02
_cell_measurement_theta_min      2.26
_cell_volume                     3521.9(2)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27309
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.277
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.154
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0659 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.8961.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       Block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.319
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     938
_refine_ls_number_reflns         12196
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0281P)^2^+0.7938P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0926
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8816
_reflns_number_total             12196
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01400f2.cif
_cod_data_source_block           mo_20240229advi053_0m
_cod_original_formula_sum        'C44 H33.80 N2 O2.40 P Se'
_cod_database_code               7160285
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.852
_shelx_estimated_absorpt_t_min   0.689
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O6-H6A = O6-H6B
 0.85 with sigma of 0.01
 C20-H7A
 3.569 with sigma of 0.01
 C20-H7B
 4.407 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O6 \\sim O7: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.02
within 2A
Uanis(O6) \\sim Ueq, Uanis(O7) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(O7)=Sof(H7A)=Sof(H7B)=0.3*(1-FVAR(2))
 Sof(O6)=Sof(H6A)=Sof(H6B)=0.3*FVAR(2)
 Fixed Sof: O5(0.5) H5A(0.5) H5B(0.5)
5.a Free rotating group:
 O5(H5A,H5B), O6(H6A,H6B), O7(H7A,H7B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37),
 C38(H38), C39(H39), C40(H40), C42(H42), C43(H43), C44(H44), C45(H45), C46(H46),
  C48(H48), C49(H49), C50(H50), C51(H51), C52(H52), C54(H54), C55(H55),
 C56(H56), C57(H57), C58(H58), C60(H60), C61(H61), C62(H62), C63(H63), C64(H64),
  C66(H66), C67(H67), C68(H68), C69(H69), C70(H70), C72(H72), C73(H73),
 C74(H74), C75(H75), C76(H76), C78(H78), C79(H79), C80(H80), C81(H81), C82(H82),
  C84(H84), C85(H85), C86(H86), C87(H87), C88(H88)
;
_shelx_res_checksum              2981
_olex2_submission_special_instructions 'No special instructions were received'