Asymmetric Friedel-Crafts Alkylation of α-Substituted β-Nitroacrylates: Access to β(2,2)-Amino Acids Bearing Indolic All-Carbon Quaternary Stereocenters
Weng, Jian-Quan; Deng, Qiao-Man; Wu, Liang; Xu, Kai; Wu, Hao; Liu, Ren-Rong; Gao, Jian-Rong; Jia, Yi-Xia; Organic Letters 16 (2014) 776–779; doi:10.1021/ol403480v

data_1513482
_publ_section_title
;
 Asymmetric Friedel-Crafts Alkylation of \a-Substituted \b-Nitroacrylates:
 Access to \b(2,2)-Amino Acids Bearing Indolic All-Carbon Quaternary
 Stereocenters
;
_journal_coden_ASTM              ORLEF7
_journal_issue                   3
_journal_name_full               'Organic Letters'
_journal_page_first              776
_journal_page_last               779
_journal_paper_doi               10.1021/ol403480v
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C21 H21 Br N2 O4'
_chemical_formula_weight         445.31
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.322(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.0332(4)
_cell_length_b                   8.4710(4)
_cell_length_c                   12.9591(6)
_cell_measurement_reflns_used    1840
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      23.4250
_cell_measurement_theta_min      3.8830
_cell_volume                     1051.46(8)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      303(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4794
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    1.983
_exptl_absorpt_correction_T_max  0.6925
_exptl_absorpt_correction_T_min  0.5877
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.024(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.792
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3371
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.792
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1168
_reflns_number_gt                2727
_reflns_number_total             3371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403480v_si_002.cif
_cod_data_source_block           p
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-20
;
_cod_original_sg_symbol_H-M      'P2(1)   '
_cod_database_code               1513482