Synthesis of Substituted Tetralins and Benzosuberans via BF3·OEt2-Mediated Formal (4 + 2) and (5 + 2) Stereocontrolled Cycloaddition of 4-Alkenols with Veratrol.
Chang, Meng-Yang; Cheng, Yu-Chieh; Organic letters 18 (2016) 608–611; doi:10.1021/acs.orglett.5b03696

data_1541925
_publ_section_title
;
 Synthesis of Substituted Tetralins and Benzosuberans via
 BF3&#x00B7;OEt2-Mediated Formal (4 + 2) and (5 + 2) Stereocontrolled
 Cycloaddition of 4-Alkenols with Veratrol.
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_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              608
_journal_page_last               611
_journal_paper_doi               10.1021/acs.orglett.5b03696
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C25 H32 O3 S'
_chemical_formula_weight         412.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.0500(8)
_cell_length_b                   11.2326(5)
_cell_length_c                   24.8893(13)
_cell_measurement_reflns_used    4493
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.5569
_cell_measurement_theta_min      2.3595
_cell_volume                     4487.1(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
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_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
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_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            35134
_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.396
_diffrn_reflns_theta_min         1.636
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.9087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
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_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+1.4957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3240
_reflns_number_total             4590
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03696_si_011.cif
_cod_data_source_block           150804LT
_cod_depositor_comments
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The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1541918--1541929.cif.
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_cod_database_code               1541925
_shelxl_version_number           2014/6
_shelx_res_checksum              46587
_shelx_hkl_checksum              36859