Synthesis of Diastereoenriched 1-Indanones via Double-Base Cooperatively Promoted 1,4-<i>Oxo</i>-Migration/Cyclization of β-Alkynyl Ketones.
Shi, Hao-Nan; Huang, Min-Hua; Hao, Wen-Juan; Tu, Xing-Chao; Tu, Shu-Jiang; Jiang, Bo; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02525

data_4037645
_publ_section_title
;
 Synthesis of Diastereoenriched 1-Indanones via Double-Base Cooperatively
 Promoted 1,4-<i>Oxo</i>-Migration/Cyclization of \b-Alkynyl Ketones.
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_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02525
_journal_year                    2019
_chemical_formula_sum            'C23 H19.5 Br Cl N O4'
_chemical_formula_weight         489.26
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.329(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7013(8)
_cell_length_b                   6.5826(7)
_cell_length_c                   38.629(4)
_cell_measurement_reflns_used    2188
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.865
_cell_measurement_theta_min      2.361
_cell_volume                     2203.0(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_av_sigmaI/netI    0.0955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10661
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    2.016
_exptl_absorpt_correction_T_max  0.8886
_exptl_absorpt_correction_T_min  0.5388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             994
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_coef       0.018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     610
_refine_ls_number_reflns         5484
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1344
_refine_ls_R_factor_gt           0.0859
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1155P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2115
_refine_ls_wR_factor_ref         0.2286
_reflns_number_gt                3008
_reflns_number_total             5484
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b02525_si_003.cif
_cod_data_source_block           190818a
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      Pn
_cod_original_formula_sum        'C23 H19.50 Br Cl N O4'
_cod_database_code               4037645