Enantioselective Friedel–Crafts C2-alkylation of 3-substituted indoles with trifluoropyruvates and cyclic N-sulfonyl α-ketiminoesters
Huang, Bing-Bing; Wu, Liang; Liu, Ren-Rong; Xing, Ling-Ling; Liang, Ren-Xiao; Jia, Yi-Xia; Organic Chemistry Frontiers 5 (2018) 929–; doi:10.1039/C7QO01014A

data_1553948
_publ_section_title
;
 Enantioselective Friedel--Crafts C2-alkylation of 3-substituted indoles
 with trifluoropyruvates and cyclic N-sulfonyl \a-ketiminoesters
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              929
_journal_paper_doi               10.1039/C7QO01014A
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C17 H15.5 N2 O3.5 S'
_chemical_formula_weight         335.87
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2017-11-01 deposited with the CCDC.
2017-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.525(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1217(7)
_cell_length_b                   8.2301(4)
_cell_length_c                   15.9865(9)
_cell_measurement_reflns_used    2391
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.1480
_cell_measurement_theta_min      4.0510
_cell_volume                     1627.15(16)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_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      298(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         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0509
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7827
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.9473
_exptl_absorpt_correction_T_min  0.9373
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             702
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5415
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0956P)^2^+0.3201P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.1627
_reflns_number_gt                4310
_reflns_number_total             5415
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo01014a2.cif
_cod_data_source_block           p
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 

2022-04-19
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C34 H31 N4 O7 S2'
_cod_original_formula_weight         671.75
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1627.15(15)
_cod_original_sg_symbol_H-M      'P2(1)   '
_cod_database_code               1553948