Catalytic Enantioselective Friedel-Crafts/Michael Addition Reactions of Indoles to Ethenetricarboxylates
Shoko Yamazaki; Yuko Iwata; Journal of Organic Chemistry 71 (2006) 739–743; doi:10.1021/jo052041p

data_4021409
_publ_section_title
;
 Catalytic Enantioselective Friedel-Crafts/Michael
 Addition Reactions of Indoles to Ethenetricarboxylates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              739
_journal_page_last               743
_journal_paper_doi               10.1021/jo052041p
_journal_volume                  71
_journal_year                    2006
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C22 H27 Br N2 O5 '
_chemical_formula_sum            'C22 H27 Br N2 O5'
_chemical_formula_weight         479.376
_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'
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 100.242(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.0060(5)
_cell_length_b                   11.1950(8)
_cell_length_c                   13.0820(11)
_cell_measurement_temperature    298
_cell_volume                     1153.82(15)
_computing_cell_refinement       Scalepack(HKL)
_computing_data_collection       'DIP Image plate'
_computing_data_reduction        'maXus (Mackay et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.823
_diffrn_measured_fraction_theta_max 0.823
_diffrn_measurement_device       'DIP Image plate'
_diffrn_measurement_method       IP
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.04328
_diffrn_orient_matrix_UB_12      -0.11873
_diffrn_orient_matrix_UB_13      0.01278
_diffrn_orient_matrix_UB_21      0.03211
_diffrn_orient_matrix_UB_22      -0.00272
_diffrn_orient_matrix_UB_23      0.08343
_diffrn_orient_matrix_UB_31      -0.07114
_diffrn_orient_matrix_UB_32      0.01424
_diffrn_orient_matrix_UB_33      0.02784
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3833
_diffrn_reflns_theta_full        25.66
_diffrn_reflns_theta_max         25.66
_diffrn_reflns_theta_min         3.64
_exptl_absorpt_coefficient_mu    1.815
_exptl_absorpt_correction_T_max  0.170
_exptl_absorpt_correction_T_min  0.273
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
Sphere (Maslen, 1992)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Cube
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.031(13)
_refine_ls_extinction_coef       0.035(4)
_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   1.025
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3210
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0812P)^2^+0.3621P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1351
_reflns_number_gt                2836
_reflns_number_total             3210
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052041psi20050929_115044.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'P 21          '
_cod_original_formula_sum        'C22 H27 Br N2 O5 '
_cod_database_code               4021409