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_7115524
_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            'C24 H26 Br N3 O2'
_chemical_formula_weight         468.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.780(4)
_cell_length_b                   13.453(6)
_cell_length_c                   15.304(6)
_cell_measurement_reflns_used    3784
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.42
_cell_volume                     2219.4(16)
_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 0.999
_diffrn_measured_fraction_theta_max 1.000
_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  0.0444
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9621
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.592
_diffrn_reflns_theta_min         2.016
_exptl_absorpt_coefficient_mu    1.877
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
; 
 Flack x determined using 1112 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.004(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4143
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0080P)^2^] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0429
_refine_ls_wR_factor_ref         0.0439
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3137
_reflns_number_total             4143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc01929f2.cif
_cod_data_source_block           a30916b
_cod_original_cell_volume        2219.6(16)
_cod_database_code               7115524
_shelx_estimated_absorpt_t_min   0.753
_shelx_estimated_absorpt_t_max   0.779
_shelxl_version_number           2013-2
_shelx_res_checksum              96454