Construction of 4-hydroxycoumarin derivatives with adjacent quaternary and tertiary stereocenters <i>via</i> ternary catalysis.
Zhang, Mengchu; Zhang, Tianyuan; Yu, Sifan; Qiu, Huang; Yusuf, Abdulla; Xu, Xinfang; Qian, Yu; Hu, Wenhao; Chemical science 14 (2023) 11850–11857; doi:10.1039/d3sc03452f

data_1570131
_publ_section_title
;
 Construction of 4-hydroxycoumarin derivatives with adjacent quaternary
 and tertiary stereocenters <i>via</i> ternary catalysis.
;
_journal_issue                   42
_journal_name_full               'Chemical science'
_journal_page_first              11850
_journal_page_last               11857
_journal_paper_doi               10.1039/d3sc03452f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C34 H29 N O4'
_chemical_formula_sum            'C34 H29 N O4'
_chemical_formula_weight         515.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-06
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-22 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                95.502(3)
_cell_angle_beta                 95.621(3)
_cell_angle_gamma                113.780(4)
_cell_formula_units_Z            2
_cell_length_a                   8.5398(3)
_cell_length_b                   10.1848(5)
_cell_length_c                   16.9463(5)
_cell_measurement_reflns_used    10809
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.5330
_cell_measurement_theta_min      2.6470
_cell_volume                     1327.39(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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     70.00 101.00   0.50    0.08    --   44.84-150.00  80.00   62
  2  \w    104.00 129.00   0.50    0.16    --  105.85-150.00  80.00   50
  3  \w     72.00  98.00   0.50    0.16    --  105.85-150.00  80.00   52
  4  \w     39.00  65.00   0.50    0.16    --  105.85-150.00  80.00   52
  5  \w     37.00  63.00   0.50    0.16    --  105.85-125.00   0.00   52
  6  \w     71.00 112.00   0.50    0.16    --  105.85-125.00   0.00   82
  7  \w     46.00 111.00   0.50    0.16    --  105.85-125.00 -60.00  130
  8  \w     55.00 111.00   0.50    0.16    --  105.85-125.00 -90.00  112
  9  \w     73.00  98.00   0.50    0.16    --  105.85-123.00-117.00   50
 10  \w     30.00  93.00   0.50    0.08    --   44.84-123.00-117.00  126
 11  \w     81.00 106.00   0.50    0.16    --  105.85 -94.00  60.00   50
 12  \w     33.00  66.00   0.50    0.16    --  105.85 -94.00  60.00   66
 13  \w     38.00  63.00   0.50    0.16    --  105.85 -77.00 120.00   50
 14  \w     71.00 106.00   0.50    0.16    --  105.85 -77.00 120.00   70
 15  \w     45.00  71.00   0.50    0.16    --  105.85 -77.00  60.00   52
 16  \w     34.00  71.00   0.50    0.16    --  105.85 -61.00 -90.00   74
 17  \w     90.00 116.00   0.50    0.16    --  105.85  15.00 -30.00   52
 18  \w    133.00 176.00   0.50    0.16    --  105.85  15.00 -30.00   86
 19  \w     82.00 174.00   0.50    0.16    --  105.85  77.00  30.00  184
 20  \w     89.00 137.00   0.50    0.16    --  105.85  61.00-150.00   96
 21  \w    152.00 177.00   0.50    0.16    --  105.85  61.00-150.00   50
 22  \w     98.00 132.00   0.50    0.16    --  105.85 123.00 -36.00   68
 23  \w     62.00 116.00   0.50    0.08    --   44.84 150.00 125.00  108
 24  \w     91.00 116.00   0.50    0.16    --  105.85 150.00 125.00   50
 25  \w     81.00 125.00   0.50    0.16    --  105.85 125.00 -90.00   88
 26  \w    142.00 175.00   0.50    0.16    --  105.85 125.00 -90.00   66
 27  \w    -24.00  29.00   0.50    0.08    --  -44.84  19.00-120.00  106
 28  \w    -24.00  13.00   0.50    0.08    --  -44.84  19.00-150.00   74
 29  \w    -20.00   6.00   0.50    0.08    --  -44.84  19.00 -60.00   52
 30  \w    -23.00  32.00   0.50    0.08    --  -44.84  19.00 -30.00  110
 31  \w   -110.00 -31.00   0.50    0.16    -- -100.00 123.00 -36.00  158
 32  \w    -57.00 -30.00   0.50    0.08    --  -44.84 123.00 -36.00   54
 33  \w    -72.00 -27.00   0.50    0.16    -- -100.00 150.00 125.00   90
 34  \w   -129.00 -77.00   0.50    0.16    -- -100.00 150.00 125.00  104
 35  \w    -92.00 -67.00   0.50    0.08    --  -44.84 150.00 125.00   50
 36  \w    -66.00 -34.00   0.50    0.16    -- -100.00  77.00 120.00   64
 37  \w    -65.00 -26.00   0.50    0.16    -- -100.00  61.00 120.00   78
 38  \w   -102.00 -74.00   0.50    0.16    -- -100.00  77.00 120.00   56
 39  \w    -79.00 -27.00   0.50    0.16    -- -100.00  77.00 -30.00  104
 40  \w    -69.00 -26.00   0.50    0.16    -- -100.00  61.00-180.00   86
 41  \w   -118.00 -82.00   0.50    0.16    -- -100.00 -30.00-120.00   72
 42  \w   -174.00-130.00   0.50    0.16    -- -100.00 -30.00-120.00   88
 43  \w   -174.00-108.00   0.50    0.16    -- -100.00 -30.00 -30.00  132
 44  \w   -171.00 -82.00   0.50    0.16    -- -100.00 -30.00 120.00  178
 45  \w    -66.00 -28.00   0.50    0.08    --  -44.84 -77.00 -90.00   76
 46  \w   -117.00 -74.00   0.50    0.08    --  -44.84 -77.00 -90.00   86
 47  \w   -147.00-122.00   0.50    0.16    -- -100.00-123.00-117.00   50
 48  \w    -95.00 -57.00   0.50    0.08    --  -44.84-150.00  80.00   76
 49  \w   -135.00-110.00   0.50    0.16    -- -100.00-150.00  80.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1847117000
_diffrn_orient_matrix_UB_12      -0.0536598000
_diffrn_orient_matrix_UB_13      0.0214061000
_diffrn_orient_matrix_UB_21      -0.0736240000
_diffrn_orient_matrix_UB_22      -0.0225356000
_diffrn_orient_matrix_UB_23      -0.0893951000
_diffrn_orient_matrix_UB_31      -0.0147533000
_diffrn_orient_matrix_UB_32      -0.1566918000
_diffrn_orient_matrix_UB_33      -0.0091220000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14703
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.798
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
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    1.290
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0619
_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^)+(0.1273P)^2^+0.2312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.1720
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4201
_reflns_number_total             4700
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03452f2.cif
_cod_data_source_block           20230504-zmc0751-1_auto
_cod_depositor_comments
'Adding full bibliography for 1570130--1570133.cif.'
_cod_database_code               1570131
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N'
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.877
_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 Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C27(H27A,H27B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2A), C4(H4), C3(H3), C22(H22), C14(H14), C33(H33), C29(H29),
 C18(H18), C15(H15), C30(H30), C31(H31), C32(H32), C25(H25), C16(H16), C23(H23),
  C17(H17), C24(H24)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              77796
_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 3.085
_oxdiff_exptl_absorpt_empirical_full_min 0.290