H2SO4-Mediated Stereocontrolled Annulation of Oxygenated Naphthalenes and 4-Alkenols: One-Pot Synthesis of Tetanthrenes.
Chang, Meng-Yang; Hsiao, Yu-Ting; The Journal of organic chemistry 82 (2017) 11594–11602; doi:10.1021/acs.joc.7b02291

data_4032931
_publ_section_title
;
 H2SO4-Mediated Stereocontrolled Annulation of Oxygenated Naphthalenes and
 4-Alkenols: One-Pot Synthesis of Tetanthrenes.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11594
_journal_page_last               11602
_journal_paper_doi               10.1021/acs.joc.7b02291
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C29 H27 O3 S'
_chemical_formula_weight         455.56
_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
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_cell_angle_beta                 103.400(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4191(8)
_cell_length_b                   13.6805(10)
_cell_length_c                   15.3386(11)
_cell_measurement_reflns_used    7858
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3151
_cell_measurement_theta_min      2.7302
_cell_volume                     2535.1(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
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_computing_publication_material  'Bruker 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 0.998
_diffrn_measured_fraction_theta_max 0.981
_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  0.0280
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20557
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.494
_diffrn_reflns_theta_min         1.686
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.9484
_exptl_absorpt_correction_T_min  0.8726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.22
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_exptl_crystal_size_min          0.15
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_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0519P)^2^+1.4279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1032
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4295
_reflns_number_total             5158
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02291_si_001.cif
_cod_data_source_block           170637lt_sq_9c_CCDC_1568160
_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 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032923--4032931.cif.
;
_cod_database_code               4032931
_shelxl_version_number           2014/6
_shelx_res_checksum              79140
_shelx_hkl_checksum              70345
_shelx_fab_checksum              44226