Organoselenium and DMAP co-catalysis: regioselective synthesis of medium-sized halolactones and bromooxepanes from unactivated alkenes.
Verma, Ajay; Jana, Sadhan; Durga Prasad, Ch; Yadav, Abhimanyu; Kumar, Sangit; Chemical communications (Cambridge, England) 52 (2016) 4179–4182; doi:10.1039/c5cc10245f

data_7118750
_publ_section_title
;
 Organoselenium and DMAP co-catalysis: regioselective synthesis of
 medium-sized halolactones and bromooxepanes from unactivated alkenes.
;
_journal_issue                   22
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4179
_journal_page_last               4182
_journal_paper_doi               10.1039/c5cc10245f
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C14  H14  Br2  O2  Se'
_chemical_formula_sum            'C14 H14 Br2 O2 Se'
_chemical_formula_weight         453.01
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2015-03-12T08:45:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-01-20 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                84.638(4)
_cell_angle_beta                 85.762(4)
_cell_angle_gamma                75.567(4)
_cell_formula_units_Z            2
_cell_length_a                   7.8195(7)
_cell_length_b                   8.6185(8)
_cell_length_c                   11.8731(11)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      25.401
_cell_measurement_theta_min      2.448
_cell_measurement_wavelength     0.71073
_cell_volume                     770.45(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25951
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.401
_diffrn_reflns_theta_min         2.448
_exptl_absorpt_coefficient_mu    7.618
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.953
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.035
_refine_diff_density_min         -1.456
_refine_diff_density_rms         0.199
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0945P)^2^+0.7123P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.129
_refine_ls_wR_factor_ref         0.1324
_reflns_number_gt                2534
_reflns_number_total             2843
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc10245f2.cif
_cod_data_source_block           Catalyst_NBS
_cod_depositor_comments
'Adding full bibliography for 7118747--7118751.cif.'
_cod_database_code               7118750