Annulative π-Extension (APEX) of Heteroarenes with Dibenzosiloles and Dibenzogermoles by Palladium/o-Chloranil Catalysis.
Ozaki, Kyohei; Matsuoka, Wataru; Ito, Hideto; Itami, Kenichiro; Organic letters 19 (2017) 1930–1933; doi:10.1021/acs.orglett.7b00684

data_1545962
_publ_section_title
;
 Annulative \p-Extension (APEX) of Heteroarenes with Dibenzosiloles and
 Dibenzogermoles by Palladium/o-Chloranil Catalysis.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1930
_journal_page_last               1933
_journal_paper_doi               10.1021/acs.orglett.7b00684
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C20 H11 Br S'
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_space_group_crystal_system      monoclinic
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_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                90
_cell_angle_beta                 97.590(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1414(5)
_cell_length_b                   15.2261(18)
_cell_length_c                   18.358(2)
_cell_measurement_reflns_used    3911
_cell_measurement_temperature    123(2)
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_cell_measurement_theta_min      3.4
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Rigaku CrystalClear-SM Expert 2.1 b29
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_computing_data_collection
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Rigaku CrystalClear-SM Expert 2.1 b29
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_computing_data_reduction
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Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
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_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      123(2)
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_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
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Rigaku CrystalClear-SM Expert 2.1 b29
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10270
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.489
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    3.024
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_description       Block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
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_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0212
_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^)+(0.0335P)^2^+0.6326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0544
_refine_ls_wR_factor_ref         0.0569
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2199
_reflns_number_total             2479
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00684_si_002.cif
_cod_data_source_block           3da
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               1545962
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.519
_shelx_estimated_absorpt_t_max   0.864
_shelx_res_checksum              54311
_shelx_hkl_checksum              70375