Sequential One-Pot Vilsmeier-Haack and Organocatalyzed Mannich Cyclizations to Functionalized Benzoindolizidines and Benzoquinolizidines.
Outin, Johanne; Quellier, Pauline; Bélanger, Guillaume; The Journal of organic chemistry 85 (2020) 4712–4729; doi:10.1021/acs.joc.9b03449

data_4038074
_publ_section_title
;
 Sequential One-Pot Vilsmeier-Haack and Organocatalyzed Mannich
 Cyclizations to Functionalized Benzoindolizidines and
 Benzoquinolizidines.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4712
_journal_page_last               4729
_journal_paper_doi               10.1021/acs.joc.9b03449
_journal_volume                  85
_journal_year                    2020
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C15 H19 N1 O3'
_chemical_formula_sum            'C15 H19 N O3'
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_symmetry_space_group_name_Hall  '-P 2yn'
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_cell_measurement_temperature    173(2)
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_cell_volume                     1328.52(4)
_computing_cell_refinement       'SAINT V8.27B integration software'
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_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
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_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       '\k-geometry diffractometer'
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_diffrn_orient_matrix_UB_22      -0.123273
_diffrn_orient_matrix_UB_23      0.156659E-1
_diffrn_orient_matrix_UB_31      0.480528E-1
_diffrn_orient_matrix_UB_32      0.158594E-1
_diffrn_orient_matrix_UB_33      0.693842E-1
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_R_equivalents  0.0581
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_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        70
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;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
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_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
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_refine_diff_density_max         0.228
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0044(8)
_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   1.04
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.058
_refine_ls_R_factor_gt           0.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0805P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1367
_reflns_number_gt                2044
_reflns_number_total             2520
_reflns_threshold_expression     >2\s(I)
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_cod_depositor_comments
'Adding full bibliography for 4038072--4038076.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038074