Diastereoselective synthesis of tetrahydropyrans via Prins-Ritter and Prins-arylthiolation cyclization reactions.
Hazarika, Nabajyoti; Sarmah, Barnali; Bordoloi, Manobjyoti; Phukan, Prodeep; Baishya, Gakul; Organic & biomolecular chemistry 15 (2017) 2003–2012; doi:10.1039/c6ob02692c

data_7155482
_publ_section_title
;
 Diastereoselective synthesis of tetrahydropyrans via Prins-Ritter and
 Prins-arylthiolation cyclization reactions.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2003
_journal_page_last               2012
_journal_paper_doi               10.1039/c6ob02692c
_journal_volume                  15
_journal_year                    2017
_chemical_formula_sum            'C17 H24 Br N O2'
_chemical_formula_weight         354.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-09-01 deposited with the CCDC.
2017-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.2548(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8738(4)
_cell_length_b                   16.4725(5)
_cell_length_c                   7.3033(2)
_cell_measurement_temperature    296(2)
_cell_volume                     1610.26(8)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            22334
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.960
_exptl_absorpt_coefficient_mu    12.500
_exptl_crystal_density_diffrn    2.536
_exptl_crystal_F_000             1140
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.697
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.697
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0214
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0813
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2552
_reflns_number_total             2854
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02692c2.cif
_cod_data_source_block           11
_cod_depositor_comments
;
          Adding full bibliography for 7155482.cif.

2018-02-03
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C H Br N O'
_cod_original_formula_units_Z    20
_cod_original_formula_weight     122.94
_cod_database_code               7155482
_shelxl_version_number           2014-3
_shelx_res_checksum              51053