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_1546313
_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         'C16 H17 O2 P'
_chemical_formula_sum            'C16 H17 O2 P'
_chemical_formula_weight         272.26
_chemical_name_common            'Fiaud's acid'
_chemical_name_systematic
'(2R,5R)-1-hydroxy-2,5-diphenylphospholane 1-oxide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-04-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.767(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.549(2)
_cell_length_b                   5.7466(5)
_cell_length_c                   11.4612(12)
_cell_measurement_reflns_used    6127
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.25
_cell_volume                     1429.3(2)
_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)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.981
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10052
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         1.846
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1068 before and 0.0569 after correction. The Ratio of minimum to maximum transmission is 0.8766. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 887 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.20(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2409
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0634P)^2^+0.5247P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1177
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.904
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                2216
_reflns_number_total             2409
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01383_si_003.cif
_cod_data_source_block           A373-084-SS
_cod_depositor_comments          'Adding full bibliography for 1546313.cif.'
_cod_database_code               1546313
_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
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C6(H6), C15(H15), C10(H10), C7(H7), C14(H14), C12(H12), C8(H8),
 C9(H9), C13(H13)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              70586
_shelx_hkl_checksum              73321
_olex2_submission_special_instructions 'No special instructions were received'