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_4038075
_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         'C19 H27 N1 O3'
_chemical_formula_sum            'C19 H27 N O3'
_chemical_formula_weight         317.42
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_atom_sites_solution_secondary   difmap
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_audit_creation_date             2016-10-28T10:33:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                81.5820(10)
_cell_angle_beta                 82.6750(10)
_cell_angle_gamma                85.3380(10)
_cell_formula_units_Z            4
_cell_length_a                   9.1272(2)
_cell_length_b                   9.8101(2)
_cell_length_c                   19.4090(5)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.7795
_cell_measurement_theta_min      4.5657
_cell_measurement_wavelength     1.54186
_cell_volume                     1701.63(7)
_computing_cell_refinement       'SAINT V8.27B 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)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.969
_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      -0.618615E-1
_diffrn_orient_matrix_UB_12      0.236423E-1
_diffrn_orient_matrix_UB_13      -0.395837E-1
_diffrn_orient_matrix_UB_21      -0.749951E-1
_diffrn_orient_matrix_UB_22      0.512453E-1
_diffrn_orient_matrix_UB_23      0.305189E-1
_diffrn_orient_matrix_UB_31      0.529245E-1
_diffrn_orient_matrix_UB_32      0.864688E-1
_diffrn_orient_matrix_UB_33      -0.158818E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22493
_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
_diffrn_reflns_theta_max         70.89
_diffrn_reflns_theta_min         2.32
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         6351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0878P)^2^+0.3397P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1431
_reflns_number_gt                5319
_reflns_number_total             6351
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo9b03449_si_004.cif
_cod_data_source_block           cu_belanger_jo4_116_0m
_cod_depositor_comments
'Adding full bibliography for 4038072--4038076.cif.'
_cod_database_code               4038075