Organocatalytic asymmetric synthesis of β,β-diaryl ketones via one-pot tandem dehydration/1,6-addition/decarboxylation transformation of β-keto acids and 4-hydroxybenzyl alcohols.
Niu, Jia-Pan; Nie, Jing; Li, Shen; Ma, Jun-An; Chemical communications (Cambridge, England) 56 (2020) 8687–8690; doi:10.1039/d0cc02213f

data_7126766
_publ_section_title
;
 Organocatalytic asymmetric synthesis of \b,\b-diaryl ketones via one-pot
 tandem dehydration/1,6-addition/decarboxylation transformation of \b-keto
 acids and 4-hydroxybenzyl alcohols.
;
_journal_issue                   61
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8687
_journal_page_last               8690
_journal_paper_doi               10.1039/d0cc02213f
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H14 O3'
_chemical_formula_sum            'C15 H14 O3'
_chemical_formula_weight         242.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc25fv1j
_audit_creation_date             2020-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-11 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8696(4)
_cell_length_b                   10.0626(8)
_cell_length_c                   20.1420(16)
_cell_measurement_reflns_used    9317
_cell_measurement_temperature    170
_cell_measurement_theta_max      74.672
_cell_measurement_theta_min      4.390
_cell_volume                     1189.66(16)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      170
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16116
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.833
_diffrn_reflns_theta_min         4.390
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1657 before and 0.0844 after correction. The Ratio of minimum to maximum transmission is 0.7604. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 901 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+0.3622P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2302
_reflns_number_total             2447
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02213f2.cif
_cod_data_source_block           0608648c_0m
_cod_depositor_comments
'Adding full bibliography for 7126766--7126768.cif.'
_cod_database_code               7126766
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.894
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C12(H12), C1(H1A), C3(H3), C11(H11), C5(H5), C2(H2A),
 C4(H4)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'