Fiaud's Acid: A Brønsted Acid Catalyst for Enantioselective Friedel-Crafts Alkylation of Indoles with 2-Alkene-1,4-diones.
Chatterjee, Sourav; Hintermann, Lukas; Mandal, Madhumita; Achari, Anushree; Gupta, Sreya; Jaisankar, Parasuraman; Organic letters 19 (2017) 3426–3429; doi:10.1021/acs.orglett.7b01383

data_1547091
_publ_section_title
;
 Fiaud's Acid: A Br\/onsted Acid Catalyst for Enantioselective
 Friedel-Crafts Alkylation of Indoles with 2-Alkene-1,4-diones.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3426
_journal_page_last               3429
_journal_paper_doi               10.1021/acs.orglett.7b01383
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C25 H21 N O2'
_chemical_formula_sum            'C25 H21 N O2'
_chemical_formula_weight         367.42
_chemical_name_common            '3-alkylated indole'
_chemical_name_systematic
(S)-2-(2-methyl-1H-indol-3-yl)-1,4-diphenylbutane-1,4-dione
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-Apr-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 89.910(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2212(12)
_cell_length_b                   13.1633(13)
_cell_length_c                   12.1650(11)
_cell_measurement_reflns_used    7096
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.92
_cell_measurement_theta_min      2.27
_cell_volume                     1957.0(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27900
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.577
_diffrn_reflns_theta_min         1.666
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1426 before and 0.0729 after correction. The Ratio of minimum to maximum transmission is 0.9058. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       Block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1672 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(9)
_refine_ls_extinction_coef       0.042(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   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         8648
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0613
_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^)+(0.0960P)^2^+0.3180P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.2207
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                4668
_reflns_number_total             8648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01383_si_004.cif
_cod_data_source_block           A261-031
_cod_depositor_comments
;

2019-03-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C25 H21 N O2)'
_cod_original_formula_sum        'C50 H42 N2 O4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     734.85
_cod_database_code               1547091
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00C(H00C), C00P(H00P)
2.b Secondary CH2 refined with riding coordinates:
 C00S(H00D,H00E), C00T(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 N005(H005), N006(H006), C00G(H00G), C00M(H00M), C00R(H00R), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Z(H00Z), C010(H010), C012(H012),
 C013(H013), C014(H014), C015(H015), C016(H016), C017(H017), C018(H018),
 C019(H019), C01A(H01F), C01B(H01G), C01C(H01D), C01D(H01E), C01E(H01K),
 C01F(H01L), C01G(H01M), C01H(H01H), C01I(H01I), C01J(H01J), C01K(H01N)
2.d Idealised Me refined as rotating group:
 C00Y(H00F,H00H,H00I), C011(H01A,H01B,H01C)
;
_shelx_res_checksum              61809
_shelx_hkl_checksum              21287
_olex2_submission_special_instructions 'No special instructions were received'