Nitro-, Azo-, and Amino Derivatives of Ebselen: Synthesis, Structure, and Cytoprotective Effects.
Singh, Vijay P.; Poon, Jia-Fei; Yan, Jiajie; Lu, Xi; Ott, Marjam Karlsson; Butcher, Ray J.; Gates, Paul J.; Engman, Lars; The Journal of organic chemistry 82 (2017) 313–321; doi:10.1021/acs.joc.6b02418

data_4032095
_publ_section_title
;
 Nitro-, Azo-, and Amino Derivatives of Ebselen: Synthesis, Structure, and
 Cytoprotective Effects.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              313
_journal_page_last               321
_journal_paper_doi               10.1021/acs.joc.6b02418
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C28 H20 N4 O2 Se2, 2(C H Cl3)'
_chemical_formula_sum            'C30 H22 Cl6 N4 O2 Se2'
_chemical_formula_weight         841.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
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_atom_sites_solution_secondary   difmap
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_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.883(7)
_cell_length_b                   12.0629(12)
_cell_length_c                   15.901(5)
_cell_measurement_reflns_used    2182
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      40.7398
_cell_measurement_theta_min      3.1787
_cell_volume                     3240(3)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1199
_diffrn_reflns_av_unetI/netI     0.1279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -18
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_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18727
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
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_diffrn_reflns_theta_min         3.185
_exptl_absorpt_coefficient_mu    2.814
_exptl_absorpt_correction_T_max  0.737
_exptl_absorpt_correction_T_min  0.583
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'dark brown-black'
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.2732
_exptl_crystal_size_mid          0.2258
_exptl_crystal_size_min          0.1348
_refine_diff_density_max         0.885
_refine_diff_density_min         -1.097
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         6174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0707
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0493P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1754
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3650
_reflns_number_total             6174
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02418_si_001.cif
_cod_data_source_block           for_compound_7b
_cod_depositor_comments
'Adding full bibliography for 4032095--4032096.cif.'
_cod_database_code               4032095
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              67458
_shelx_hkl_checksum              59809