MeOTf-catalyzed Friedel-Crafts alkylation of benzoxazolones, benzothiazolones, indolinones and benzimidazolones with activated secondary alcohols.
Duari, Surajit; Biswas, Subrata; Roy, Arnab; Maity, Srabani; Elsharif, Asma M.; Biswas, Srijit; Organic & biomolecular chemistry 22 (2024) 8801–8810; doi:10.1039/d4ob01372g

data_7160174
_publ_section_title
;
 MeOTf-catalyzed Friedel-Crafts alkylation of benzoxazolones,
 benzothiazolones, indolinones and benzimidazolones with activated
 secondary alcohols.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8801
_journal_page_last               8810
_journal_paper_doi               10.1039/d4ob01372g
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C21 H17 N O2'
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_weight         315.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-04
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-06-28 deposited with the CCDC.	2024-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.779(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0708(12)
_cell_length_b                   12.580(2)
_cell_length_c                   21.139(4)
_cell_measurement_reflns_used    7321
_cell_measurement_temperature    229.24
_cell_measurement_theta_max      26.97
_cell_measurement_theta_min      2.52
_cell_volume                     1613.6(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      229.24
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.989
_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  0.0823
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16013
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.005
_diffrn_reflns_theta_min         3.239
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.5025
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1538 before and 0.1135 after correction.
The Ratio of minimum to maximum transmission is 0.6746.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.051(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0626
_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^)+(0.0927P)^2^+0.5215P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1824
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2781
_reflns_number_total             3487
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01372g2.cif
_cod_data_source_block           om36
_cod_depositor_comments
'Adding full bibliography for 7160174--7160175.cif.'
_cod_original_cell_volume        1613.5(5)
_cod_database_code               7160174
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C9(H9)
1.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
1.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_shelx_res_checksum              83859
_shelx_hkl_checksum              29929
_olex2_submission_special_instructions 'No special instructions were received'