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_7126767
_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 rm
_chemical_formula_moiety         'C21 H17 Cl O2'
_chemical_formula_sum            'C21 H17 Cl O2'
_chemical_formula_weight         336.80
_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.cc24jrm2
_audit_creation_date             2019-10-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-06 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                   5.339(4)
_cell_length_b                   15.845(10)
_cell_length_c                   23.929(14)
_cell_measurement_reflns_used    1278
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.474
_cell_measurement_theta_min      2.569
_cell_volume                     2024(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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 0.976
_diffrn_measured_fraction_theta_max 0.976
_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  0.0619
_diffrn_reflns_av_unetI/netI     0.1298
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5498
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.085
_diffrn_reflns_theta_max         25.085
_diffrn_reflns_theta_min         2.571
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7856
_exptl_absorpt_correction_T_min  0.5798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker;sadabs;2018
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
TITL 258_0m_a.res in P2(1)2(1)2(1)
CELL    5.3390   15.8450   23.9290     90.00     90.00     90.00
SPGR P212121
C101 0.531 0.408 0.543 !       2.82 eA-3
C102 0.161 0.732 0.006 !       2.37 eA-3
C103 0.846 0.717 0.015 !       2.14 eA-3
C104 0.594 0.339 0.527 !       1.87 eA-3
C105 0.341 0.363 0.516 !       1.81 eA-3
C106 0.306 0.659 0.996 !       1.72 eA-3
C107 0.712 0.360 0.526 !       1.68 eA-3
C108 0.034 0.126 0.490 !       1.56 eA-3
C109 0.253 0.350 0.475 !       1.50 eA-3
C110 0.923 0.203 0.473 !       1.45 eA-3
C111 0.468 0.281 0.467 !       1.31 eA-3
C112 0.379 0.718 0.021 !       1.17 eA-3
C113 0.529 0.329 0.553 !       1.15 eA-3
C114 0.806 0.800 0.002 !       1.14 eA-3
C115 0.717 0.126 0.440 !       1.13 eA-3
C116 0.728 0.874 0.012 !       1.13 eA-3
C117 0.501 0.308 0.568 !       1.12 eA-3
C118 0.691 0.686 0.018 !       1.06 eA-3
Q119 0.810 0.652 0.985 !       1.06 eA-3
C120 0.754 0.191 0.463 !       1.01 eA-3
Q121 0.587 0.176 0.460 !       1.01 eA-3
Q122 0.900 0.327 0.556 !       1.00 eA-3
Q123 0.907 0.043 0.413 !       1.00 eA-3
C124 0.963 0.188 0.519 !       1.00 eA-3
Q125 0.289 0.295 0.442 !       0.94 eA-3
C126 0.249 0.752 0.965 !       0.94 eA-3
C127 0.649 0.341 0.567 !       0.92 eA-3
Q128 0.939 0.628 0.953 !       0.85 eA-3
C129 0.411 0.956 0.986 !       0.83 eA-3
Q130 0.749 0.625 0.947 !       0.80 eA-3
Q131 0.887 0.768 0.927 !       0.80 eA-3
C132 0.091 0.583 0.981 !       0.80 eA-3
Q133 0.813 0.757 0.960 !       0.77 eA-3
Q134 0.497 0.398 0.624 !       0.74 eA-3
C135 0.930 0.554 0.985 !       0.74 eA-3
Q136 0.366 0.752 0.927 !       0.74 eA-3
Q137 0.946 0.936 0.956 !       0.74 eA-3
C138 0.583 0.721 0.972 !       0.74 eA-3
Q139 0.311 0.658 0.942 !       0.72 eA-3
Q140 0.161 0.375 0.615 !       0.72 eA-3
Q141 0.075 0.656 0.946 !       0.72 eA-3
C142 0.969 0.879 0.958 !       0.70 eA-3
C143 0.091 0.766 0.975 !       0.69 eA-3
C144 0.556 0.694 0.986 !       0.68 eA-3
Q145 0.851 0.555 0.947 !       0.66 eA-3
Q146 0.045 1.006 0.417 !       0.66 eA-3
Q147 0.702 0.670 0.944 !       0.66 eA-3
Q148 0.372 0.402 0.627 !       0.65 eA-3
Q149 0.747 0.843 0.087 !       0.65 eA-3
Q150 0.129 0.933 0.974 !       0.64 eA-3
C151 0.681 0.060 0.433 !       0.64 eA-3
Q152 0.720 0.579 0.984 !       0.62 eA-3
Q153 0.549 0.721 0.934 !       0.62 eA-3
Q154 0.567 0.589 0.955 !       0.60 eA-3
Q155 0.973 1.001 0.504 !       0.60 eA-3
Q156 0.099 0.995 0.540 !       0.60 eA-3
Q157 0.775 0.981 0.965 !       0.60 eA-3
Q158 0.319 0.839 0.868 !       0.59 eA-3
Q159 0.336 0.936 0.897 !       0.59 eA-3
C160 0.939 0.368 0.522 !       0.59 eA-3
Q161 0.054 0.546 0.935 !       0.59 eA-3
Q162 0.401 0.348 0.592 !       0.59 eA-3
Q163 0.903 0.703 0.941 !       0.58 eA-3
Q164 0.271 0.511 0.100 !       0.58 eA-3
Q165 0.929 0.994 0.936 !       0.56 eA-3
Q166 0.608 0.205 0.582 !       0.55 eA-3
Q167 0.695 0.192 0.415 !       0.54 eA-3
Q168 0.802 0.938 0.898 !       0.54 eA-3
Q169 0.654 0.899 0.102 !       0.54 eA-3
C170 0.914 0.655 0.101 !       0.53 eA-3
Q171 0.958 0.139 0.595 !       0.51 eA-3
Q172 0.669 0.656 0.101 !       0.51 eA-3
Q173 0.464 0.660 0.090 !       0.51 eA-3
C174 0.312 0.377 0.448 !       0.51 eA-3
Q175 0.435 0.334 0.632 !       0.50 eA-3
;
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 430 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.1358
_refine_ls_R_factor_gt           0.0596
_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^)+(0.0568P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1483
_reflns_Friedel_coverage         0.622
_reflns_Friedel_fraction_full    0.868
_reflns_Friedel_fraction_max     0.868
_reflns_number_gt                1709
_reflns_number_total             3363
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02213f2.cif
_cod_data_source_block           258_0m_sq
_cod_depositor_comments
'Adding full bibliography for 7126766--7126768.cif.'
_cod_database_code               7126767
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.971
_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:
 C21(H21), C20(H20), C15(H15), C18(H18), C6(H6), C5(H5), C3(H3), C2(H2),
 C17(H17), C13(H13), C11(H11), C12(H12), C14(H14)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'