Organocatalytic asymmetric cascade 1,6-addition/hemiketalization/retro-Henry reaction of ortho-hydroxyphenyl-substituted p-QMs with α-nitroketones.
Zhou, Jing; Bai, Li-Juan; Liang, Guo-Juan; Xu, Qi-Gui; Zhou, Li-Ping; Zhou, Hui; Organic & biomolecular chemistry 18 (2020) 2641–2645; doi:10.1039/d0ob00397b

data_7157406
_publ_section_title
;
 Organocatalytic asymmetric cascade
 1,6-addition/hemiketalization/retro-Henry reaction of
 ortho-hydroxyphenyl-substituted p-QMs with \a-nitroketones.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2641
_journal_page_last               2645
_journal_paper_doi               10.1039/d0ob00397b
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H32 Cl N O5'
_chemical_formula_sum            'C29 H32 Cl N O5'
_chemical_formula_weight         510.00
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-08-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-02 deposited with the CCDC.	2020-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.360(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6244(3)
_cell_length_b                   9.8943(3)
_cell_length_c                   14.3864(5)
_cell_measurement_reflns_used    4367
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9350
_cell_measurement_theta_min      4.5930
_cell_volume                     1366.00(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -48.00 -16.00   1.00    1.00    --  -33.50 -57.00-180.00   32
  2  \w    -92.00 -66.00   1.00    1.00    --  -33.50 -57.00-180.00   26
  3  \w    -62.00  36.00   1.00    1.00    --  -33.50  77.00 -60.00   98
  4  \w     33.00  59.00   1.00    1.00    --   36.47  57.00 120.00   26
  5  \w     16.00  51.00   1.00    1.00    --   36.47  37.00-120.00   35
  6  \w     52.00  78.00   1.00    1.00    --   36.47  77.00-150.00   26
  7  \w     11.00  61.00   1.00    1.00    --   36.47  77.00  60.00   50
  8  \w     43.00  90.00   1.00    1.00    --   36.47  19.00-180.00   47
  9  \w     -2.00  51.00   1.00    1.00    --   36.47 -77.00 150.00   53
 10  \w      3.00  31.00   1.00    1.00    --   36.47  88.00 171.58   28
 11  \w     58.00  95.00   1.00    1.00    --   36.47 178.00-180.00   37
 12  \w     58.00  91.00   1.00    1.00    --   36.47 178.00   0.00   33
 13  \w     21.00  47.00   1.00    1.00    --   36.47  37.00 -60.00   26
 14  \w     58.00  88.00   1.00    1.00    --   36.47 178.00  60.00   30
 15  \w     18.00 105.00   1.00    1.00    --   36.47  57.00  60.00   87
 16  \w     73.00 100.00   1.00    1.00    --   36.47  37.00 -60.00   27
 17  \w     61.00 102.00   1.00    1.00    --   36.47 178.00 120.00   41
 18  \w     16.00  45.00   1.00    1.00    --   36.47  77.00-120.00   29
 19  \w     50.00 103.00   1.00    1.00    --   36.47  77.00-120.00   53
 20  \w     37.00 111.00   1.00    5.00    --  108.00-111.00 -90.00   74
 21  \w    123.00 169.00   1.00    5.00    --  108.00  61.00-150.00   46
 22  \w     38.00  85.00   1.00    5.00    --  108.00 -94.00  60.00   47
 23  \w     82.00 115.00   1.00    5.00    --  108.00  30.00-120.00   33
 24  \w    113.00 176.00   1.00    5.00    --  108.00  77.00 150.00   63
 25  \w     85.00 116.00   1.00    5.00    --  108.00  30.00-180.00   31
 26  \w     88.00 114.00   1.00    5.00    --  108.00  61.00-150.00   26
 27  \w     68.00 175.00   1.00    5.00    --  108.00  15.00 -90.00  107
 28  \w     89.00 115.00   1.00    5.00    --  108.00  61.00 120.00   26
 29  \w     83.00 109.00   1.00    5.00    --  108.00  30.00 150.00   26
 30  \w     88.00 115.00   1.00    5.00    --  108.00  61.00  90.00   27
 31  \w     79.00 105.00   1.00    5.00    --  108.00  77.00 150.00   26
 32  \w    153.00 178.00   1.00    5.00    --  108.00 111.00-120.00   25
 33  \w    134.00 173.00   1.00    5.00    --  108.00 111.00 -60.00   39
 34  \w    112.00 175.00   1.00    5.00    --  108.00  77.00  90.00   63
 35  \w     88.00 114.00   1.00    5.00    --  108.00  45.00  90.00   26
 36  \w     79.00 104.00   1.00    5.00    --  108.00  77.00  90.00   25
 37  \w    118.00 174.00   1.00    5.00    --  108.00  77.00 120.00   56
 38  \w     90.00 126.00   1.00    5.00    --  108.00  61.00-180.00   36
 39  \w     80.00 106.00   1.00    5.00    --  108.00  77.00 120.00   26
 40  \w     56.00 118.00   1.00    5.00    --  108.00 -77.00 -90.00   62
 41  \w     82.00 112.00   1.00    5.00    --  108.00  30.00-150.00   30
 42  \w    147.00 173.00   1.00    5.00    --  108.00  45.00  90.00   26
 43  \w    128.00 155.00   1.00    5.00    --  108.00  77.00-180.00   27
 44  \w     90.00 118.00   1.00    5.00    --  108.00  61.00 150.00   28
 45  \w     79.00 105.00   1.00    5.00    --  108.00  77.00-180.00   26
 46  \w     79.00 105.00   1.00    5.00    --  108.00  77.00-150.00   26
 47  \w    102.00 128.00   1.00    5.00    --  108.00 111.00-120.00   26
 48  \w     87.00 119.00   1.00    5.00    --  108.00  30.00 120.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0572167000
_diffrn_orient_matrix_UB_12      -0.0633222000
_diffrn_orient_matrix_UB_13      -0.0871894000
_diffrn_orient_matrix_UB_21      -0.1401891000
_diffrn_orient_matrix_UB_22      0.0271477000
_diffrn_orient_matrix_UB_23      -0.0558293000
_diffrn_orient_matrix_UB_31      0.0532150000
_diffrn_orient_matrix_UB_32      0.1396083000
_diffrn_orient_matrix_UB_33      -0.0286930000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11041
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         4.608
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.546
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       prism
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1608 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(19)
_refine_ls_extinction_coef       0.0135(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4633
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0813P)^2^+0.0758P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1350
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    0.887
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                4182
_reflns_number_total             4633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00397b2.cif
_cod_data_source_block           201908203
_cod_depositor_comments          'Adding full bibliography for 7157406.cif.'
_cod_database_code               7157406
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c20h20n4o4Cl1
_shelx_estimated_absorpt_t_max   0.861
_shelx_estimated_absorpt_t_min   0.813
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O5(H5A)
2.b Ternary CH refined with riding coordinates:
 C7(H7)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C10(H10), C14(H14), C25(H25), C26(H26), C27(H27),
 C28(H28), C29(H29)
2.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.386
_oxdiff_exptl_absorpt_empirical_full_min 0.848