One-Pot Two-Step Multicomponent Process of Indole and Other Nitrogenous Heterocycles or Amines toward α-Oxo-acetamidines.
Martinez-Ariza, Guillermo; McConnell, Nicholas; Hulme, Christopher; Organic letters 18 (2016) 1864–1867; doi:10.1021/acs.orglett.6b00634

data_1542953
_publ_section_title
;
 One-Pot Two-Step Multicomponent Process of Indole and Other Nitrogenous
 Heterocycles or Amines toward \a-Oxo-acetamidines.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1864
_journal_page_last               1867
_journal_paper_doi               10.1021/acs.orglett.6b00634
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C22 H15 Br N2 O'
_chemical_formula_sum            'C22 H15 Br N2 O'
_chemical_formula_weight         403.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-02-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_cell_angle_alpha                71.2120(17)
_cell_angle_beta                 89.4040(16)
_cell_angle_gamma                76.7450(15)
_cell_formula_units_Z            2
_cell_length_a                   7.9172(4)
_cell_length_b                   9.9111(6)
_cell_length_c                   12.2268(7)
_cell_measurement_reflns_used    5721
_cell_measurement_temperature    150.
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.24
_cell_volume                     882.00(9)
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0284
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11621
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_min         1.763
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.343
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0637 before and 0.0381 after correction.
The Ratio of minimum to maximum transmission is 0.8499.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.132
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0424P)^2^+0.4736P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0785
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3045
_reflns_number_total             3338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00634_si_002.cif
_cod_data_source_block           mo_ch233_0m_a
_cod_depositor_comments
'Adding full bibliography for 1542953--1542954.cif.'
_cod_database_code               1542953
_shelxl_version_number           2012-9
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C1(H1), C22(H22), C5(H5), C2(H2), C15(H15), C11(H11), C12(H12),
 C21(H21), C6(H6), C18(H18), C14(H14), C13(H13), C19(H19), C20(H20)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'