A direct approach for the expedient synthesis of unsymmetrical ethers by employing bromodimethylsulfonium bromide (BDMS) mediated C–S bond cleavage of naphthalene-2-ol sulfides
Islam, Kobirul; Sidick Basha, R.; Dar, Ajaz A.; Das, Deb K.; Khan, Abu T.; RSC Adv. 5 (2015) 79759–; doi:10.1039/C5RA14563E

data_7222258
_publ_section_title
;
 A direct approach for the expedient synthesis of unsymmetrical ethers by
 employing bromodimethylsulfonium bromide (BDMS) mediated C--S bond
 cleavage of naphthalene-2-ol sulfides
;
_journal_issue                   97
_journal_name_full               'RSC Adv.'
_journal_page_first              79759
_journal_paper_doi               10.1039/C5RA14563E
_journal_volume                  5
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C18 H15 Br O2'
_chemical_formula_sum            'C18 H15 Br O2'
_chemical_formula_weight         343.20
_chemical_name_common            2n
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-12-01 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.548(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1085(6)
_cell_length_b                   7.3865(4)
_cell_length_c                   16.4008(7)
_cell_measurement_reflns_used    1972
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.81
_cell_measurement_theta_min      2.37
_cell_volume                     1514.12(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_av_sigmaI/netI    0.1258
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18573
_diffrn_reflns_theta_full        28.59
_diffrn_reflns_theta_max         28.59
_diffrn_reflns_theta_min         1.75
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696.0
_exptl_crystal_recrystallization_method 'slow evaporation of DCM, chloroform'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.1849
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0412P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                1393
_reflns_number_total             3866
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra14563e2.cif
_cod_data_source_block           ki-113
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7222258