One-pot enantioselective construction of indoloquinolizidine derivatives bearing five contiguous stereocenters using aliphatic aldehydes, nitroethylenes, and tryptamine
Yu Tan; Han-Lin Luan; Hua Lin; Xing-Wen Sun; Xiao-Di Yang; Han-Qing Dong; Guo-Qiang Lin; Chem.Commun. 50 (2014) 10027–; doi:10.1039/C4cc01929F

data_7115525
_publ_section_title
;
 One-pot enantioselective construction of indoloquinolizidine derivatives
 bearing five contiguous stereocenters using aliphatic aldehydes,
 nitroethylenes, and tryptamine
;
_journal_name_full               Chem.Commun.
_journal_page_first              10027
_journal_paper_doi               10.1039/C4cc01929F
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C28 H35 N3 O2'
_chemical_formula_weight         445.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.000(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.784(5)
_cell_length_b                   8.872(4)
_cell_length_c                   14.497(7)
_cell_measurement_reflns_used    776
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.286
_cell_measurement_theta_min      2.512
_cell_volume                     1258.4(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5689
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         1.405
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       sheet
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
; 
 Flack x determined using 795 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.5(10)
_refine_ls_extinction_coef       0.017(5)
_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   0.854
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4523
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      0.867
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.1050P)^2^] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.1794
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.846
_reflns_Friedel_fraction_max     0.831
_reflns_number_gt                2207
_reflns_number_total             4523
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc01929f2.cif
_cod_data_source_block           a30711a
_cod_depositor_comments
;

2018-03-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1258.4(10)
_cod_original_formula_sum        'C56 H70 N6 O4'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     891.18
_cod_database_code               7115525
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.999
_shelxl_version_number           2013-2
_shelx_res_checksum              70066