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_7246139
_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         'C18 H22 O4'
_chemical_formula_sum            'C18 H22 O4'
_chemical_formula_weight         302.373
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-06-11
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-07-14 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.591(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0243(6)
_cell_length_b                   20.5740(16)
_cell_length_c                   11.0931(9)
_cell_measurement_reflns_used    9804
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.360
_cell_measurement_theta_min      2.70
_cell_volume                     1602.5(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.9993
_diffrn_reflns_Laue_measured_fraction_max 0.9965
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            52044
_diffrn_reflns_point_group_measured_fraction_full 0.9993
_diffrn_reflns_point_group_measured_fraction_max 0.9965
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.98
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0780 before and 0.0467 after correction.
The Ratio of minimum to maximum transmission is 0.9635.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             648.433
_refine_diff_density_max         0.2036
_refine_diff_density_min         -0.1665
_refine_diff_density_rms         0.0340
_refine_ls_d_res_high            0.7482
_refine_ls_d_res_low             10.2870
_refine_ls_goodness_of_fit_ref   1.0649
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     205
_refine_ls_number_reflns         4007
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0649
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          -0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0613P)^2^+0.2712P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -9
_reflns_limit_k_max              27
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              -7
_reflns_number_gt                3483
_reflns_number_total             4007
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2gc04684a2.cif
_cod_data_source_block           sanjay_ckh_0m_a
_cod_depositor_comments
'Adding full bibliography for 7246138--7246139.cif.'
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7246139
_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 C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C12(H12), C18(H18)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C14(H14a,H14b,H14c),
 C17(H17a,H17b,H17c)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'