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_4038072
_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         'C13 H18 N2 O1'
_chemical_formula_sum            'C13 H18 N2 O'
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_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
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_symmetry_space_group_name_Hall  '-P 2ybc'
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_cell_angle_alpha                90
_cell_angle_beta                 109.0350(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6553(2)
_cell_length_b                   11.4000(3)
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_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.6428
_cell_measurement_theta_min      4.8451
_cell_measurement_wavelength     1.54186
_cell_volume                     1149.77(5)
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_UB_11      0.429503E-1
_diffrn_orient_matrix_UB_12      0.720689E-1
_diffrn_orient_matrix_UB_13      0.496974E-1
_diffrn_orient_matrix_UB_21      0.144456E-1
_diffrn_orient_matrix_UB_22      -0.434606E-1
_diffrn_orient_matrix_UB_23      0.818153E-1
_diffrn_orient_matrix_UB_31      0.997508E-1
_diffrn_orient_matrix_UB_32      -0.247373E-1
_diffrn_orient_matrix_UB_33      0.104691E-2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_unetI/netI     0.0691
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_diffrn_reflns_limit_k_min       -13
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_diffrn_reflns_limit_l_min       -13
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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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_exptl_absorpt_coefficient_mu    0.637
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_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       newedle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0854P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1491
_reflns_number_gt                1628
_reflns_number_total             2185
_reflns_threshold_expression     >2\s(I)
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_cod_data_source_block           cu_belanger_jo_129_0m
_cod_depositor_comments
'Adding full bibliography for 4038072--4038076.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038072