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_7118747
_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_absolute_configuration rmad
_chemical_formula_moiety         'C10  H17  Br1  O2'
_chemical_formula_sum            'C10 H17 Br O2'
_chemical_formula_weight         249.14
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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             2015-12-16T19:42:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-02-05 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.094(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2235(4)
_cell_length_b                   9.7990(6)
_cell_length_c                   9.2211(6)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      25.846
_cell_measurement_theta_min      2.226
_cell_measurement_wavelength     0.71073
_cell_volume                     558.04(6)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      101(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.99
_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  0.0386
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15283
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.846
_diffrn_reflns_theta_min         2.226
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.652
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             256
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3 and Hexane'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         2.179
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.16
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     68
_refine_ls_number_reflns         2106
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0837P)^2^+2.7318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1465
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2030
_reflns_number_total             2106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc10245f2.cif
_cod_data_source_block           AV_7_M_D
_cod_depositor_comments
'Adding full bibliography for 7118747--7118751.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7118747
_shelx_res_checksum              3256