Three-Component Approach to Pyridine-Stabilized Ketenimines for the Synthesis of Diverse Heterocycles.
Massaro, Nicholas P.; Chatterji, Aayushi; Sharma, Indrajeet; The Journal of organic chemistry 84 (2019) 13676–13685; doi:10.1021/acs.joc.9b01906

data_4034545
_publ_section_title
;
 Three-Component Approach to Pyridine-Stabilized Ketenimines for the
 Synthesis of Diverse Heterocycles.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13676
_journal_page_last               13685
_journal_paper_doi               10.1021/acs.joc.9b01906
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C16 H9 Br N2 O'
_chemical_formula_sum            'C16 H9 Br N2 O'
_chemical_formula_weight         325.16
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
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_cell_angle_beta                 113.580(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.468(5)
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_cell_length_c                   23.093(4)
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_cell_measurement_temperature    100(2)
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_cell_measurement_theta_min      3.07
_cell_volume                     2495.0(8)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
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_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Mercury (CCDC, 2018)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Photon II cpad'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       6
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_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21838
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.928
_diffrn_reflns_theta_min         2.305
_exptl_absorpt_coefficient_mu    3.290
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS-2016/2 Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10. 
;
_exptl_crystal_colour            orange
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_exptl_crystal_description       block
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_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.044
_refine_diff_density_max         1.964
_refine_diff_density_min         -1.006
_refine_diff_density_rms         0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0592
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1280P)^2^+20.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1713
_refine_ls_wR_factor_ref         0.1984
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2356
_reflns_number_total             2960
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01906_si_004.cif
_cod_data_source_block           19097
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4034545
_shelx_estimated_absorpt_t_min   0.671
_shelx_estimated_absorpt_t_max   0.869
_shelx_res_checksum              25112
_shelx_hkl_checksum              33517