Hydrogen bonding network-enabled Brønsted acid-catalyzed Friedel–Crafts reactions: a green approach to access unsymmetrical diaryl- and triarylmethanes
Singh, Sanjay; Mondal, Sankalan; Vodnala, Nagaraju; Hazra, Chinmoy Kumar; Green Chemistry 25 (2023) 1014–1022; doi:10.1039/D2GC04684A

data_7246138
_publ_section_title
;
 Hydrogen bonding network-enabled Br\/onsted acid-catalyzed
 Friedel--Crafts reactions: a green approach to access unsymmetrical
 diaryl- and triarylmethanes
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              1014
_journal_page_last               1022
_journal_paper_doi               10.1039/D2GC04684A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C24 H21 F5 O4'
_chemical_formula_sum            'C24 H20 F5 O4'
_chemical_formula_weight         467.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-07-12
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-14 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                98.767(2)
_cell_angle_beta                 99.704(2)
_cell_angle_gamma                91.221(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3761(5)
_cell_length_b                   8.4007(5)
_cell_length_c                   16.0336(9)
_cell_measurement_reflns_used    8030
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.265
_cell_measurement_theta_min      2.456
_cell_volume                     1097.79(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  multi-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            43739
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.309
_diffrn_reflns_theta_min         2.456
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1196 before and 0.0589 after correction.
The Ratio of minimum to maximum transmission is 0.9488.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       block
_exptl_crystal_F_000             482
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         5456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0737P)^2^+0.3491P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1702
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3146
_reflns_number_total             5456
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc04684a2.cif
_cod_data_source_block           test1006_01_a
_cod_depositor_comments
'Adding full bibliography for 7246138--7246139.cif.'
_cod_database_code               7246138
_shelx_shelxl_version_number     2019/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C17(H17), C21(H21)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              1145
_olex2_submission_special_instructions 'No special instructions were received'