Co-catalysis between DABCO and a Brønsted acid in the catalytic [4 + 2] annulation of isatin with but-3-yn-2-one and mechanistic investigations
Wang, Qiang; Xu, Qin; Shi, Min; Organic Chemistry Frontiers 2 (2015) 211–; doi:10.1039/C4QO00323C

data_1553062
_publ_section_title
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 Co-catalysis between DABCO and a Br\/onsted acid in the catalytic [4 + 2]
 annulation of isatin with but-3-yn-2-one and mechanistic investigations
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_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              211
_journal_paper_doi               10.1039/C4QO00323C
_journal_volume                  2
_journal_year                    2015
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-04-29 deposited with the CCDC.
2015-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                108.838(3)
_cell_angle_beta                 97.636(4)
_cell_angle_gamma                94.663(4)
_cell_formula_units_Z            2
_cell_length_a                   8.1086(14)
_cell_length_b                   8.8324(16)
_cell_length_c                   13.260(2)
_cell_measurement_reflns_used    1786
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      48.627
_cell_measurement_theta_min      4.907
_cell_volume                     883.0(3)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0619
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5026
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24244
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.035(12)
_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   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3246
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0682
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1413P)^2^+0.0131P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1926
_refine_ls_wR_factor_ref         0.2173
_reflns_number_gt                2296
_reflns_number_total             3246
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4qo00323c2.cif
_cod_data_source_block           cd213215
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/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 6909 2019-04-08 15:41:33Z antanas 
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_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1553062