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_1541927
_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.
;
_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_absolute_configuration rm
_chemical_formula_sum            'C19 H19 F3 O3 S'
_chemical_formula_weight         384.40
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_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
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_cell_length_a                   5.6186(6)
_cell_length_b                   8.3590(8)
_cell_length_c                   37.132(3)
_cell_measurement_reflns_used    3694
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.9929
_cell_measurement_theta_min      3.2919
_cell_volume                     1743.9(3)
_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)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
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_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  0.0418
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_k_min       -10
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_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            14333
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.447
_diffrn_reflns_theta_min         1.097
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
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_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             800
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_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.49(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
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_refine_ls_number_reflns         3585
_refine_ls_number_restraints     132
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+1.0662P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3243
_reflns_number_total             3585
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03696_si_008.cif
_cod_data_source_block           mo_150415lt_0m_a
_cod_depositor_comments
;
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               1541927
_shelxl_version_number           2014/6
_shelx_res_checksum              75508
_shelx_hkl_checksum              17018