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_1570130
_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         'C29 H23 N O4'
_chemical_formula_sum            'C29 H23 N O4'
_chemical_formula_weight         449.48
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-05-22 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                112.6020(10)
_cell_angle_beta                 91.9090(10)
_cell_angle_gamma                104.2180(10)
_cell_formula_units_Z            2
_cell_length_a                   10.06580(10)
_cell_length_b                   10.9123(2)
_cell_length_c                   11.3400(2)
_cell_measurement_reflns_used    20022
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.5840
_cell_measurement_theta_min      4.2360
_cell_volume                     1103.30(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (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 1.000
_diffrn_measured_fraction_theta_max 0.971
_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    -63.00  26.00   0.50    0.10    --  -46.62  57.00  90.00  178
  2  \w    -44.00 -18.00   0.50    0.10    --    8.00 132.00  90.05   52
  3  \w      5.00  33.00   0.50    0.10    --   36.00  93.00  85.34   56
  4  \w     28.00 125.00   0.50    0.10    --   52.00  77.00  58.53  194
  5  \w     90.00 178.00   0.50    0.80    --  107.00 102.00 137.00  176
  6  \w    113.00 139.00   0.50    0.80    --  107.00  45.00 150.00   52
  7  \w    106.00 132.00   0.50    0.10    --   60.00  74.00 163.69   52
  8  \w     38.00  64.00   0.50    0.10    --   60.00  74.00 163.69   52
  9  \w     34.00 129.00   0.50    0.10    --   56.00  73.00 141.67  190
 10  \w     46.00  72.00   0.50    0.10    --   68.00  75.00   7.91   52
 11  \w     31.00 122.00   0.50    0.10    --   46.62  19.00 -60.00  182
 12  \w     66.00 105.00   0.50    0.80    --  107.00 -77.00   0.00   78
 13  \w     81.00 106.00   0.50    0.80    --  107.00-102.00  34.00   50
 14  \w     77.00 112.00   0.50    0.80    --  107.00-125.00  30.00   70
 15  \w     73.00 105.00   0.50    0.80    --  107.00 -94.00   0.00   64
 16  \w     85.00 112.00   0.50    0.80    --  107.00-125.00 -60.00   54
 17  \w     64.00 112.00   0.50    0.80    --  107.00-125.00 -30.00   96
 18  \w     49.00 112.00   0.50    0.80    --  107.00-125.00   0.00  126
 19  \w     45.00  70.00   0.50    0.80    --  107.00-125.00  30.00   50
 20  \w     35.00  69.00   0.50    0.80    --  107.00 -94.00   0.00   68
 21  \w     38.00  68.00   0.50    0.80    --  107.00 -61.00  30.00   60
 22  \w     35.00  68.00   0.50    0.80    --  107.00 -61.00  90.00   66
 23  \w     35.00  90.00   0.50    0.80    --  107.00 -94.00 150.00  110
 24  \w     74.00 112.00   0.50    0.80    --  107.00-125.00 150.00   76
 25  \w     34.00 112.00   0.50    0.80    --  107.00-125.00 120.00  156
 26  \w     36.00  62.00   0.50    0.80    --  107.00-125.00 150.00   52
 27  \w     -9.00  83.00   0.50    0.10    --   46.62-102.00  34.00  184
 28  \w     41.00  69.00   0.50    0.80    --  107.00 -61.00 -90.00   56
 29  \w     40.00  79.00   0.50    0.80    --  107.00 -94.00-120.00   78
 30  \w     81.00 110.00   0.50    0.80    --  107.00-125.00-150.00   58
 31  \w     78.00 105.00   0.50    0.80    --  107.00 -94.00-180.00   54
 32  \w     70.00 106.00   0.50    0.80    --  107.00 -77.00-180.00   72
 33  \w     54.00  79.00   0.50    0.80    --  107.00-125.00-150.00   50
 34  \w     37.00  64.00   0.50    0.80    --  107.00 -77.00-180.00   54
 35  \w     36.00  71.00   0.50    0.80    --  107.00 -61.00-180.00   70
 36  \w     34.00  59.00   0.50    0.80    --  107.00 -94.00-180.00   50
 37  \w     37.00  70.00   0.50    0.80    --  107.00 -61.00-120.00   66
 38  \w     36.00  63.00   0.50    0.80    --  107.00-125.00 -60.00   54
 39  \w     94.00 178.00   0.50    0.80    --  107.00  45.00 -60.00  168
 40  \w     31.00 125.00   0.50    0.10    --   52.00  70.00  33.88  188
 41  \w     31.00 129.00   0.50    0.10    --   56.00  80.00-108.52  196
 42  \w     37.00  63.00   0.50    0.10    --   60.00  75.00-121.64   52
 43  \w     33.00  58.00   0.50    0.10    --   56.00  75.00-139.50   50
 44  \w     28.00 125.00   0.50    0.10    --   52.00  77.00-157.06  194
 45  \w     23.00 120.00   0.50    0.10    --   46.62  77.00   0.00  194
 46  \w     27.00 125.00   0.50    0.10    --   52.00  79.00 -63.29  196
 47  \w     36.00  62.00   0.50    0.10    --   60.00  78.00 135.63   52
 48  \w    -17.00  27.00   0.50    0.10    --   16.00  97.00  -1.14   88
 49  \w      4.00  33.00   0.50    0.10    --   36.00  94.00-151.81   58
 50  \w    -66.00 -41.00   0.50    0.10    --  -64.00 -75.00 -47.29   50
 51  \w    -37.00 -10.00   0.50    0.10    --  -40.00 -90.00 -91.46   54
 52  \w    -63.00 -35.00   0.50    0.10    --  -60.00 -80.00 -59.05   56
 53  \w    -71.00 -45.00   0.50    0.10    --  -68.00 -75.00-166.58   52
 54  \w    -84.00 -58.00   0.50    0.80    --  -80.00 -72.00-123.10   52
 55  \w    -83.00 -58.00   0.50    0.80    --  -80.00 -73.00 -73.37   50
 56  \w    -88.00 -58.00   0.50    0.80    --  -80.00 -73.00 -86.07   60
 57  \w    -90.00 -64.00   0.50    0.80    --  -80.00 -60.00-121.97   52
 58  \w    -89.00 -63.00   0.50    0.80    --  -84.00 -73.00-163.23   52
 59  \w    -94.00 -68.00   0.50    0.80    --  -84.00 -61.00-167.36   52
 60  \w    -93.00 -67.00   0.50    0.80    --  -88.00 -71.00-174.39   52
 61  \w   -106.00 -77.00   0.50    0.80    -- -100.00 -79.00-130.44   58
 62  \w   -106.00 -76.00   0.50    0.80    -- -100.00 -77.00-120.00   60
 63  \w   -104.00 -77.00   0.50    0.80    -- -100.00 -75.00 -72.26   54
 64  \w    -94.00 -69.00   0.50    0.80    --  -92.00 -74.00 -45.47   50
 65  \w    -92.00 -58.00   0.50    0.80    --  -80.00 -73.00 -20.55   68
 66  \w    -80.00 -54.00   0.50    0.80    --  -76.00 -72.00  24.43   52
 67  \w    -62.00 -36.00   0.50    0.10    --  -60.00 -78.00  57.84   52
 68  \w    -74.00 -49.00   0.50    0.10    --  -68.00 -64.00 144.90   50
 69  \w    -71.00 -45.00   0.50    0.10    --  -68.00 -74.00 131.48   52
 70  \w    -87.00 -52.00   0.50    0.80    --  -76.00 -76.00  66.19   70
 71  \w    -85.00 -59.00   0.50    0.80    --  -80.00 -73.00  97.69   52
 72  \w    -85.00 -59.00   0.50    0.80    --  -80.00 -69.00  76.60   52
 73  \w    -88.00 -62.00   0.50    0.80    --  -84.00 -73.00  61.83   52
 74  \w    -91.00 -61.00   0.50    0.80    --  -80.00 -64.00 122.42   60
 75  \w    -88.00 -62.00   0.50    0.80    --  -84.00 -72.00 109.72   52
 76  \w    -91.00 -65.00   0.50    0.80    --  -88.00 -74.00  59.20   52
 77  \w    -84.00 -58.00   0.50    0.80    --  -80.00 -74.00   9.87   52
 78  \w    -97.00 -65.00   0.50    0.80    --  -84.00 -65.00 -55.19   64
 79  \w   -106.00 -79.00   0.50    0.80    --  -96.00 -60.00 -11.27   54
 80  \w   -107.00 -79.00   0.50    0.80    -- -100.00 -73.00 -53.25   56
 81  \w   -112.00 -83.00   0.50    0.80    -- -100.00 -77.00 -30.00   58
 82  \w   -125.00 -80.00   0.50    0.80    -- -100.00 -68.00 -90.41   90
 83  \w   -124.00 -82.00   0.50    0.80    -- -100.00 -71.00-146.41   84
 84  \w   -125.00 -78.00   0.50    0.80    -- -100.00 -74.00-113.15   94
 85  \w   -119.00 -74.00   0.50    0.10    --  -46.62-125.00-180.00   90
 86  \w   -137.00-112.00   0.50    0.10    --  -64.00 -75.00 -47.29   50
 87  \w   -119.00 -23.00   0.50    0.10    --  -46.62 -77.00  30.00  192
 88  \w    -92.00 -66.00   0.50    0.80    --  -88.00 -75.00 132.52   52
 89  \w   -101.00 -66.00   0.50    0.80    --  -84.00 -65.00 140.28   70
 90  \w   -108.00 -76.00   0.50    0.80    -- -100.00 -77.00  60.00   64
 91  \w   -105.00 -77.00   0.50    0.80    -- -100.00 -74.00  71.34   56
 92  \w   -108.00 -82.00   0.50    0.80    -- -100.00 -65.00 112.08   52
 93  \w   -112.00 -77.00   0.50    0.80    -- -100.00 -74.00 160.32   70
 94  \w   -111.00 -79.00   0.50    0.80    -- -100.00 -72.00  99.44   64
 95  \w   -110.00 -78.00   0.50    0.80    -- -100.00 -78.00 137.21   64
 96  \w   -119.00 -23.00   0.50    0.10    --  -46.62 -77.00  90.00  192
 97  \w   -116.00 -76.00   0.50    0.80    -- -100.00 -78.00  -5.10   80
 98  \w   -131.00 -74.00   0.50    0.80    --  -92.00 -64.00  17.55  114
 99  \w   -127.00 -80.00   0.50    0.80    -- -100.00 -72.00 108.96   94
100  \w   -136.00 -78.00   0.50    0.80    -- -100.00 -76.00 142.81  116
101  \w   -146.00-120.00   0.50    0.80    --  -76.00 -72.00  24.43   52
102  \w   -145.00 -80.00   0.50    0.80    -- -100.00 -68.00  -5.44  130
103  \w   -145.00-119.00   0.50    0.80    --  -80.00 -64.00 122.42   52
104  \w   -142.00-116.00   0.50    0.80    -- -100.00 -72.00  99.44   52
105  \w   -145.00 -77.00   0.50    0.80    -- -100.00 -77.00  30.00  136
106  \w   -140.00-114.00   0.50    0.80    -- -100.00 -54.00  15.05   52
107  \w   -153.00-127.00   0.50    0.80    --  -96.00 -60.00 -11.27   52
108  \w   -157.00-113.00   0.50    0.80    -- -100.00 -75.00 -72.26   88
109  \w   -168.00-142.00   0.50    0.80    -- -100.00 -79.00-130.44   52
110  \w   -156.00 -78.00   0.50    0.80    -- -100.00 -72.00-168.47  156
111  \w   -163.00-138.00   0.50    0.80    -- -100.00 -73.00 -53.25   50
112  \w   -165.00-139.00   0.50    0.80    -- -100.00 -77.00 -30.00   52
113  \w   -170.00-144.00   0.50    0.80    -- -100.00 -68.00 -90.41   52
114  \w   -173.00-131.00   0.50    0.80    -- -100.00 -74.00-113.15   84
115  \w   -173.00-140.00   0.50    0.80    -- -100.00 -77.00-120.00   66
116  \w   -170.00 -76.00   0.50    0.80    -- -100.00 -77.00-150.00  188
117  \w   -169.00 -77.00   0.50    0.80    -- -100.00 -76.00 -24.66  184
118  \w   -164.00-138.00   0.50    0.80    -- -100.00 -77.00  60.00   52
119  \w   -173.00 -86.00   0.50    0.80    -- -100.00-102.00  34.00  174
120  \w   -167.00 -81.00   0.50    0.80    -- -100.00 -65.00 172.23  172
121  \w   -173.00-124.00   0.50    0.80    -- -100.00 -65.00 112.08   98
122  \w   -173.00 -81.00   0.50    0.80    -- -100.00 -72.00  91.04  184
123  \w   -171.00-132.00   0.50    0.80    -- -100.00 -74.00 160.32   78
124  \w   -173.00-126.00   0.50    0.80    -- -100.00 -78.00 137.21   94
125  \w   -173.00 -76.00   0.50    0.80    -- -100.00 -77.00  53.55  194
126  \w   -169.00 -79.00   0.50    0.80    -- -100.00 -72.00-103.46  180
127  \w   -162.00-130.00   0.50    0.80    -- -100.00 -15.00 -90.00   64
128  \w   -172.00-100.00   0.50    0.80    -- -100.00 -49.00  59.98  144
129  \w    -82.00  13.00   0.50    0.10    --  -46.62 102.00 137.00  190
130  \w   -106.00 -27.00   0.50    0.80    -- -100.00 102.00 137.00  158
;
_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      -0.1589974000
_diffrn_orient_matrix_UB_12      -0.0350506000
_diffrn_orient_matrix_UB_13      -0.0105728000
_diffrn_orient_matrix_UB_21      -0.0126448000
_diffrn_orient_matrix_UB_22      -0.0989613000
_diffrn_orient_matrix_UB_23      -0.1425815000
_diffrn_orient_matrix_UB_31      -0.0024419000
_diffrn_orient_matrix_UB_32      -0.1198068000
_diffrn_orient_matrix_UB_33      0.0407790000
_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  0.0836
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            44222
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.040
_diffrn_reflns_theta_min         4.267
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.353
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4553
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0987P)^2^+0.2025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3918
_reflns_number_total             4553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03452f2.cif
_cod_data_source_block           zhangmch_210427_3
_cod_depositor_comments
'Adding full bibliography for 1570130--1570133.cif.'
_cod_database_code               1570130
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C3-H3
 0.91 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C16(H16), C20(H20), C24(H24), C11(H11), C19(H19), C18(H18), C26(H26),
 C17(H17), C8(H8), C27(H27), C10(H10), C9(H9)
3.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              27086
_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 1.773
_oxdiff_exptl_absorpt_empirical_full_min 0.619