Tandem Michael Addition/Amino-Nitrile Cyclization from 2-Formyl-1,4-DHP in the Synthesis of Novel Dihydroindolizine-Based Compounds
Štefan Marchalín; Barbora Baumlová; Peter Baran; Hassan Oulyadi; Adam Daïch; Journal of Organic Chemistry 71 (2006) 9114–9127; doi:10.1021/jo0615044

data_4022097
_publ_section_title
;
 Tandem Michael Addition/Amino-Nitrile Cyclization from 2-Formyl-1,4-DHP
 in the Synthesis of Novel Dihydroindolizine-Based Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9114
_journal_page_last               9127
_journal_paper_doi               10.1021/jo0615044
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C25 H27 N3 O6 S'
_chemical_formula_weight         497.55
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.072(3)
_cell_angle_beta                 92.721(3)
_cell_angle_gamma                90.565(3)
_cell_formula_units_Z            4
_cell_length_a                   10.2841(16)
_cell_length_b                   14.470(2)
_cell_length_c                   17.650(3)
_cell_measurement_temperature    298(2)
_cell_volume                     2554.9(7)
_computing_cell_refinement       'BRUKER SMART-NT V5.0'
_computing_data_collection       'BRUKER SMART-NT V5.0'
_computing_data_reduction        'BRUKER SAINT-NT V5/6.0'
_computing_molecular_graphics    'BRUKER SHELXTL-NT V5.1'
_computing_publication_material  'BRUKER SHELXTL-NT V5.1'
_computing_structure_refinement  'BRUKER SHELXTL-NT V5.1'
_computing_structure_solution    'BRUKER SHELXTL-NT V5.1'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker AXS SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.1321
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11424
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     680
_refine_ls_number_reflns         7328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.881
_refine_ls_R_factor_all          0.1561
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          1.924
_refine_ls_shift/su_mean         0.023
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0754P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1672
_reflns_number_gt                3258
_reflns_number_total             7328
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0615044si20060719_123524.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C50 H54 N6 O12 S2'
_cod_original_formula_weight         995.11
_cod_original_formula_units_Z            2
_cod_database_code               4022097