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_7126768
_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         'C22 H17 Cl O4'
_chemical_formula_sum            'C22 H17 Cl O4'
_chemical_formula_weight         380.80
_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.cc24jrn3
_audit_creation_date             2019-09-20
_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                   5.6683(8)
_cell_length_b                   12.2650(19)
_cell_length_c                   32.881(5)
_cell_measurement_reflns_used    2794
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.557
_cell_measurement_theta_min      2.478
_cell_volume                     2285.9(6)
_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      150.0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0908
_diffrn_reflns_av_unetI/netI     0.1135
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            14538
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.677
_diffrn_reflns_theta_min         2.478
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.2594
_exptl_absorpt_correction_T_min  0.1952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1160 before and 0.0741 after correction. The Ratio of minimum to maximum transmission is 0.7525. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_platon_squeeze_details
;
TITL 22019963njp3256_0m_a.res in P2(1)2(1)2(1)
CELL    5.6683   12.2650   32.8810     90.00     90.00     90.00
SPGR P212121
C101 0.747 0.351 0.537 !       5.83 eA-3
C102 0.991 0.271 0.418 !       4.70 eA-3
C103 0.250 0.341 0.462 !       4.35 eA-3
C104 0.682 0.260 0.549 !       4.03 eA-3
C105 0.185 0.315 0.616 !       4.02 eA-3
C106 0.651 0.836 0.909 !       3.90 eA-3
C107 0.997 0.239 0.569 !       3.27 eA-3
C108 0.663 0.764 0.045 !       3.20 eA-3
C109 0.679 0.157 0.423 !       2.00 eA-3
C110 0.476 0.251 0.396 !       1.40 eA-3
C111 0.153 0.668 0.984 !       1.39 eA-3
C112 0.270 0.600 0.940 !       1.36 eA-3
C113 0.316 0.275 0.561 !       1.27 eA-3
C114 0.997 0.841 0.919 !       1.23 eA-3
C115 0.345 0.695 0.930 !       1.23 eA-3
C116 0.037 0.316 0.460 !       1.03 eA-3
C117 0.541 0.122 0.563 !       1.00 eA-3
Q118 0.597 0.971 0.039 !       0.99 eA-3
C119 0.186 0.276 0.540 !       0.98 eA-3
C120 0.941 0.326 0.617 !       0.98 eA-3
C121 0.499 0.838 0.935 !       0.96 eA-3
C122 0.781 0.790-0.001 !       0.96 eA-3
Q123 0.030 0.242 0.635 !       0.96 eA-3
C124 0.568 0.752 0.009 !       0.94 eA-3
C125 0.212 0.822 0.898 !       0.94 eA-3
C126 0.036 0.803 0.952 !       0.93 eA-3
C127 0.287 0.366 0.561 !       0.91 eA-3
Q128 0.246 0.572 0.011 !       0.88 eA-3
Q129 0.845 0.098 0.421 !       0.86 eA-3
Q130 0.720 0.318 0.365 !       0.86 eA-3
C131 0.094 0.304 0.490 !       0.82 eA-3
C132 0.308 0.699 0.150 !       0.82 eA-3
C133 0.031 0.131 0.406 !       0.81 eA-3
C134 0.561 0.128 0.391 !       0.81 eA-3
C135 0.782 0.290 0.462 !       0.79 eA-3
C136 0.088 0.601 0.113 !       0.76 eA-3
Q137 0.498 0.365 0.618 !       0.76 eA-3
Q138 0.810 0.135 0.577 !       0.76 eA-3
C139 0.094 0.354 0.515 !       0.74 eA-3
C140 1.012 0.262 0.531 !       0.74 eA-3
C141 0.318 0.276 0.532 !       0.72 eA-3
Q142 0.659 0.596 0.070 !       0.72 eA-3
Q143 0.534 0.086 0.422 !       0.71 eA-3
C144 0.125 0.322 0.526 !       0.71 eA-3
C145 0.346 0.762 0.007 !       0.70 eA-3
Q146 0.381 0.577 0.022 !       0.70 eA-3
Q147 0.940 0.526 0.102 !       0.68 eA-3
Q148 0.487 0.392 0.478 !       0.67 eA-3
Q149 0.192 0.491 0.428 !       0.66 eA-3
C150 0.092 0.196 0.401 !       0.65 eA-3
Q151 0.026 0.074 0.596 !       0.63 eA-3
Q152 0.906 0.576 0.020 !       0.63 eA-3
Q153 0.692 0.072 0.446 !       0.63 eA-3
Q154 0.558 0.335 0.474 !       0.63 eA-3
Q155 0.836 0.047 0.581 !       0.62 eA-3
Q156 0.872 0.415 0.437 !       0.61 eA-3
Q157 0.132 0.465 0.438 !       0.61 eA-3
Q158 0.379 0.083 0.538 !       0.61 eA-3
Q159 0.102 0.627 0.136 !       0.60 eA-3
Q160 0.907 0.560 0.947 !       0.60 eA-3
Q161 0.682 0.804 0.175 !       0.60 eA-3
C162 0.374 0.153 0.595 !       0.60 eA-3
Q163 0.624 0.234 0.338 !       0.59 eA-3
Q164 0.688 0.072 0.596 !       0.59 eA-3
Q165 0.167 0.076 0.429 !       0.59 eA-3
Q166 0.598 0.128 0.450 !       0.59 eA-3
Q167 0.854 0.583 0.123 !       0.59 eA-3
C168 0.431 0.328 0.516 !       0.58 eA-3
Q169 0.714 0.338 0.625 !       0.58 eA-3
Q170 0.680 0.076 0.375 !       0.58 eA-3
Q171 0.843 0.843 0.820 !       0.57 eA-3
C172 0.556 0.343 0.507 !       0.56 eA-3
Q173 0.802 0.627 0.982 !       0.55 eA-3
Q174 1.001 0.463 0.484 !       0.54 eA-3
Q175 0.438 0.282 0.342 !       0.54 eA-3
Q176 0.654 0.635 0.369 !       0.54 eA-3
Q177 0.068 0.588 0.949 !       0.54 eA-3
Q178 0.087 0.592 0.028 !       0.54 eA-3
Q179 0.601 0.591 0.022 !       0.54 eA-3
Q180 0.318 0.077 0.591 !       0.53 eA-3
Q181 0.257 0.593 0.038 !       0.52 eA-3
Q182 0.909 0.206 0.167 !       0.52 eA-3
Q183 0.127 0.920 0.912 !       0.52 eA-3
Q184 0.806 0.384 0.626 !       0.52 eA-3
C185 0.129 0.780 0.118 !       0.52 eA-3
Q186 0.377 0.055 0.852 !       0.51 eA-3
Q187 0.148 0.526 0.145 !       0.51 eA-3
Q188 0.224 0.068 0.584 !       0.51 eA-3
Q189 0.283 0.121 0.564 !       0.51 eA-3
Q190 0.090 0.713 0.863 !       0.51 eA-3
;
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 783 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0605P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1310
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                2705
_reflns_number_total             4261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02213f2.cif
_cod_data_source_block           22019963njp3256_0m_sq
_cod_depositor_comments
'Adding full bibliography for 7126766--7126768.cif.'
_cod_database_code               7126768
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C13(H13), C12(H12), C4(H4), C22(H22), C18(H18), C1(H1), C9(H9),
 C20(H20), C2(H2), C19(H19), C10(H10), C21(H21)
2.c Idealised tetrahedral OH refined as rotating group:
 O25(H25), O26(H26)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'