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_7118749
_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  O2  Se'
_chemical_formula_sum            'C14 H14 O2 Se'
_chemical_formula_weight         293.21
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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             2015-03-02T19:00:59-00:00
_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                90
_cell_angle_beta                 95.797(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1527(10)
_cell_length_b                   26.213(4)
_cell_length_c                   8.0982(14)
_cell_measurement_reflns_used    36
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      25.468
_cell_measurement_theta_min      2.645
_cell_measurement_wavelength     0.71073
_cell_volume                     1299.4(4)
_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      301(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18829
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.468
_diffrn_reflns_theta_min         2.645
_exptl_absorpt_coefficient_mu    2.877
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.59
_refine_diff_density_min         -0.74
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2409
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0250P)^2^+3.0286P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.11
_refine_ls_wR_factor_ref         0.1149
_reflns_number_gt                1988
_reflns_number_total             2409
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc10245f2.cif
_cod_data_source_block           catalyst
_cod_depositor_comments
'Adding full bibliography for 7118747--7118751.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7118749