Synthesis of 1-Aryltetralins and 1-Arylnaphthalenes via (4 + 2) Annulation of β-Ketosulfones with Styryl Bromides.
Chang, Meng-Yang; Cheng, Yu-Chieh; Organic letters 18 (2016) 1682–1685; doi:10.1021/acs.orglett.6b00603

data_1543003
_publ_section_title
;
 Synthesis of 1-Aryltetralins and 1-Arylnaphthalenes via (4 + 2)
 Annulation of \b-Ketosulfones with Styryl Bromides.
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_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1682
_journal_page_last               1685
_journal_paper_doi               10.1021/acs.orglett.6b00603
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C24 H21 Cl O3 S'
_chemical_formula_weight         424.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 108.933(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.1277(9)
_cell_length_b                   11.8028(6)
_cell_length_c                   22.7698(13)
_cell_measurement_reflns_used    2930
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.3515
_cell_measurement_theta_min      2.5143
_cell_volume                     4354.0(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)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(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  0.0398
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18440
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.386
_diffrn_reflns_theta_min         1.891
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4445
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0491P)^2^+1.8872P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1195
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2975
_reflns_number_total             4445
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00603_si_002.cif
_cod_data_source_block           151107_0m
_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 
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_cod_database_code               1543003
_shelxl_version_number           2014/6
_shelx_res_checksum              25774
_shelx_hkl_checksum              4954