Conformationally Locked Bridged Bicyclic Diselenides: Synthesis, Structure, Se···O Interaction, and Theoretical Studies
Devarajulu Sureshkumar; Venkataraman Ganesh; Srinivasan Chandrasekaran; Journal of Organic Chemistry 72 (2007) 5313–5319; doi:10.1021/jo070705k

data_4024012
_publ_contact_author_address
; 
Department of Organic Chemistry
Indian Institute of Science
Bangaloe 560012, Karnataka
India
;
_publ_contact_author_email       scn@orgchem.iisc.ernet.in
_publ_contact_author_fax         '+91 80 23602423'
_publ_contact_author_name        'Prof. Srinivasan Chandrasekaran'
_publ_contact_author_phone       '+91 80 22932404'
_publ_section_title
;
 Conformationally Locked Bridged Bicyclic Diselenides: Synthesis,
 Structure, Se&#x00B7;&#x00B7;&#x00B7;O Interaction, and Theoretical Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5313
_journal_page_last               5319
_journal_paper_doi               10.1021/jo070705k
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C15 H20 Cl3 N O3 S Se2'
_chemical_formula_sum            'C15 H20 Cl3 N O3 S Se2'
_chemical_formula_weight         558.65
_chemical_melting_point          439.15
_chemical_name_common            'locked diselenide'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.743(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.909(10)
_cell_length_b                   10.839(7)
_cell_length_c                   12.948(9)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.37
_cell_volume                     2085(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18813
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    4.045
_exptl_absorpt_correction_T_max  0.7934
_exptl_absorpt_correction_T_min  0.5137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.966
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.233
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.233
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0678P)^2^+4.6417P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_ref         0.1581
_reflns_number_gt                2909
_reflns_number_total             3669
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo070705ksi20070405_075852_02.cif
_cod_data_source_block           compound12
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '166 deg' was changed to '439.15' -
it was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

2020-10-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_moiety     'C12 H16 Cl2.40 N0.80 O2.40 S0.80 Se1.60'
_cod_original_formula_sum        'C12 H16 Cl2.40 N0.80 O2.40 S0.80 Se1.60'
_cod_original_formula_units_Z    5
_cod_original_formula_weight     446.92
_cod_database_code               4024012