General Approach toward Aspidospermatan-Type Alkaloids Using One-Pot Vilsmeier–Haack Cyclization and Azomethine Ylide Cycloaddition
Hauduc, Clémence; Bélanger, Guillaume; The Journal of Organic Chemistry  (2017) –; doi:10.1021/acs.joc.7b00345

data_4032442
_publ_section_title
;
 General Approach toward Aspidospermatan-Type Alkaloids Using One-Pot
 Vilsmeier--Haack Cyclization and Azomethine Ylide Cycloaddition
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.7b00345
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H22 N2 O5'
_chemical_formula_sum            'C17 H22 N2 O5'
_chemical_formula_weight         334.37
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2016-09-14T15:09:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 106.651(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.349(2)
_cell_length_b                   8.7736(7)
_cell_length_c                   15.5435(19)
_cell_measurement_reflns_used    9521
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.4289
_cell_measurement_theta_min      3.6383
_cell_measurement_wavelength     1.54186
_cell_volume                     3311.9(6)
_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 0.965
_diffrn_measured_fraction_theta_max 0.963
_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      0.410528E-1
_diffrn_orient_matrix_UB_12      0.770834E-2
_diffrn_orient_matrix_UB_13      0.178168E-1
_diffrn_orient_matrix_UB_21      0.29057E-2
_diffrn_orient_matrix_UB_22      -0.111285
_diffrn_orient_matrix_UB_23      0.143024E-1
_diffrn_orient_matrix_UB_31      -0.299995E-3
_diffrn_orient_matrix_UB_32      -0.230425E-1
_diffrn_orient_matrix_UB_33      -0.63114E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_unetI/netI     0.1389
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8585
_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         70.13
_diffrn_reflns_theta_min         3.64
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.823
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.459
_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    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         5048
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1692
_refine_ls_R_factor_gt           0.1038
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2502
_refine_ls_wR_factor_ref         0.3105
_reflns_number_gt                2829
_reflns_number_total             5048
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo7b00345_si_002.cif
_cod_data_source_block           cu_belanger_ch5124h2_0m
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4032442