Enantioselective [2 + 2] photocycloaddition of quinolone using a <i>C</i><sub>1</sub>-symmetric chiral phosphoric acid as a visible-light photocatalyst.
Takagi, Ryukichi; Tanimoto, Takaaki; Organic & biomolecular chemistry 20 (2022) 3940–3947; doi:10.1039/d2ob00607c

data_7158649
_publ_section_title
;
 Enantioselective [2 + 2] photocycloaddition of quinolone using a
 <i>C</i><sub>1</sub>-symmetric chiral phosphoric acid as a visible-light
 photocatalyst.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3940
_journal_page_last               3947
_journal_paper_doi               10.1039/d2ob00607c
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H19 N O'
_chemical_formula_sum            'C15 H19 N O'
_chemical_formula_weight         229.31
_chemical_melting_point          135
_chemical_name_common
1,1,2,2-tetramethyl-cyclobuta-quinolin-3(1H)-one
_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_creation_date             2022-03-10
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2022-03-19 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.11510(10)
_cell_length_b                   8.44480(10)
_cell_length_c                   21.3264(2)
_cell_measurement_reflns_used    20763
_cell_measurement_temperature    100
_cell_measurement_theta_max      76.2120
_cell_measurement_theta_min      4.0680
_cell_volume                     1281.41(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.27a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.27a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.27a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_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 0.998
_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   -108.00 -64.00   0.50    0.50    --  -41.38-140.00  60.00   88
  2  \w    -86.00 -60.00   0.50    0.50    --  -41.38 140.00 119.00   52
  3  \w    -66.00 -17.00   0.50    0.50    --  -41.38 130.00 -54.00   98
  4  \w     28.00 103.00   0.50    0.50    --   41.38-140.00  60.00  150
  5  \w     28.00  97.00   0.50    0.50    --   41.38-130.00-125.00  138
  6  \w   -138.00-113.00   0.50    0.50    -- -104.00-130.00-125.00   50
  7  \w   -123.00 -97.00   0.50    0.50    -- -104.00-140.00  60.00   52
  8  \w   -100.00 -75.00   0.50    0.50    -- -104.00 140.00 119.00   50
  9  \w    -73.00 -33.00   0.50    0.50    -- -104.00 130.00 -54.00   80
 10  \w     75.00 171.00   0.50    0.50    --  108.75 130.00 -54.00  192
 11  \w     94.00 120.00   0.50    0.50    --  108.75-140.00  60.00   52
 12  \w     94.00 123.00   0.50    0.50    --  108.75 140.00 119.00   58
 13  \w     38.00  64.00   0.50    0.50    --  108.75-130.00-125.00   52
 14  \w    -34.00  35.00   0.50    0.50    --  -41.38  38.00 120.00  138
 15  \w    -64.00 -37.00   0.50    0.50    --  -41.38 -19.00   0.00   54
 16  \w   -105.00 -78.00   0.50    0.50    --  -41.38 -77.00 150.00   54
 17  \w   -121.00 -82.00   0.50    0.50    --  -41.38 -19.00   0.00   78
 18  \w    -43.00 -13.00   0.50    0.50    --  -41.38 -77.00 150.00   60
 19  \w     18.00  70.00   0.50    0.50    --   41.38  77.00 -90.00  104
 20  \w     27.00  79.00   0.50    0.50    --   41.38  57.00 120.00  104
 21  \w     70.00 117.00   0.50    0.50    --   41.38  38.00 120.00   94
 22  \w     13.00  87.00   0.50    0.50    --   41.38  77.00-120.00  148
 23  \w     22.00  54.00   0.50    0.50    --   41.38  38.00 120.00   64
 24  \w     13.00  71.00   0.50    0.50    --   41.38  77.00 -30.00  116
 25  \w     20.00  98.00   0.50    0.50    --   41.38  57.00-150.00  156
 26  \w     76.00 109.00   0.50    0.50    --   41.38  77.00 -30.00   66
 27  \w     49.00  75.00   0.50    0.50    --   41.38  77.00   0.00   52
 28  \w     14.00  75.00   0.50    0.50    --   41.38  77.00 150.00  122
 29  \w     14.00  43.00   0.50    0.50    --   41.38  77.00   0.00   58
 30  \w     13.00  62.00   0.50    0.50    --   41.38  77.00  60.00   98
 31  \w     91.00 116.00   0.50    0.50    --   41.38  77.00 -90.00   50
 32  \w   -110.00 -75.00   0.50    0.50    -- -104.00 -77.00  27.76   70
 33  \w   -173.00-127.00   0.50    0.50    -- -104.00 -72.00 -16.70   92
 34  \w   -170.00-144.00   0.50    0.50    -- -104.00 -64.00  86.97   52
 35  \w   -132.00 -80.00   0.50    0.50    -- -104.00 -61.00-180.00  104
 36  \w   -101.00 -75.00   0.50    0.50    -- -104.00 -77.00   0.00   52
 37  \w   -171.00-126.00   0.50    0.50    -- -104.00 -77.00 120.00   90
 38  \w   -102.00 -76.00   0.50    0.50    -- -104.00 -77.00-180.00   52
 39  \w   -106.00 -80.00   0.50    0.50    -- -104.00 -61.00  60.00   52
 40  \w   -102.00 -77.00   0.50    0.50    -- -104.00 -72.00 -16.70   50
 41  \w   -134.00 -79.00   0.50    0.50    -- -104.00 -67.00 156.92  110
 42  \w   -100.00 -75.00   0.50    0.50    -- -104.00 -77.00  90.00   50
 43  \w   -146.00-120.00   0.50    0.50    -- -104.00 -58.00 -10.34   52
 44  \w   -118.00 -75.00   0.50    0.50    -- -104.00 -77.00 146.11   86
 45  \w   -166.00-137.00   0.50    0.50    -- -104.00 -77.00-180.00   58
 46  \w   -106.00 -80.00   0.50    0.50    -- -104.00 -61.00 -90.00   52
 47  \w   -113.00 -77.00   0.50    0.50    -- -104.00 -71.00 -88.44   72
 48  \w   -100.00 -75.00   0.50    0.50    -- -104.00 -77.00  60.00   50
 49  \w   -163.00-138.00   0.50    0.50    -- -104.00 -60.00-134.63   50
 50  \w   -105.00 -80.00   0.50    0.50    -- -104.00 -61.00  30.00   50
 51  \w   -105.00 -78.00   0.50    0.50    -- -104.00 -70.00  99.86   54
 52  \w   -103.00 -77.00   0.50    0.50    -- -104.00 -77.00 120.00   52
 53  \w   -103.00 -77.00   0.50    0.50    -- -104.00 -76.00-129.93   52
 54  \w   -109.00 -81.00   0.50    0.50    -- -104.00 -60.00-134.63   56
 55  \w   -102.00 -77.00   0.50    0.50    -- -104.00 -73.00 131.81   50
 56  \w   -104.00 -78.00   0.50    0.50    -- -104.00 -70.00 -59.62   52
 57  \w   -108.00 -83.00   0.50    0.50    -- -104.00 -54.00 -21.05   50
 58  \w   -174.00-143.00   0.50    0.50    -- -104.00 -77.00   0.00   62
 59  \w   -107.00 -82.00   0.50    0.50    -- -104.00 -58.00 -10.34   50
 60  \w   -166.00-139.00   0.50    0.50    -- -104.00 -77.00 146.11   54
 61  \w   -105.00 -80.00   0.50    0.50    -- -104.00 -65.00 143.19   50
 62  \w   -103.00 -78.00   0.50    0.50    -- -104.00 -70.00-173.22   50
 63  \w   -148.00 -77.00   0.50    0.50    -- -104.00 -72.00-107.05  142
 64  \w   -168.00-142.00   0.50    0.50    -- -104.00 -77.00-150.00   52
 65  \w   -104.00 -76.00   0.50    0.50    -- -104.00 -77.00-150.00   56
 66  \w   -104.00 -79.00   0.50    0.50    -- -104.00 -66.00 117.05   50
 67  \w   -100.00 -75.00   0.50    0.50    -- -104.00 -77.00 -60.00   50
 68  \w   -100.00 -75.00   0.50    0.50    -- -104.00 -77.00 -92.69   50
 69  \w   -175.00-140.00   0.50    0.50    -- -104.00 -77.00 -92.69   70
 70  \w   -102.00 -77.00   0.50    0.50    -- -104.00 -71.00 -49.22   50
 71  \w   -163.00-137.00   0.50    0.50    -- -104.00 -77.00 -60.00   52
 72  \w   -126.00 -82.00   0.50    0.50    -- -104.00 -64.00  86.97   88
 73  \w   -106.00 -81.00   0.50    0.50    -- -104.00 -65.00 148.70   50
 74  \w   -103.00 -78.00   0.50    0.50    -- -104.00 -70.00 -26.31   50
 75  \w   -100.00 -75.00   0.50    0.50    -- -104.00 -77.00 -30.00   50
 76  \w     80.00 112.00   0.50    0.50    --  108.75-125.00 -90.00   64
 77  \w     77.00 112.00   0.50    0.50    --  108.75-125.00 150.00   70
 78  \w     44.00  72.00   0.50    0.50    --  108.75-125.00 -90.00   56
 79  \w     53.00  97.00   0.50    0.50    --  108.75-125.00-150.00   88
 80  \w     39.00  72.00   0.50    0.50    --  108.75-125.00 150.00   66
 81  \w     36.00  67.00   0.50    0.50    --  108.75 -61.00  60.00   62
 82  \w     38.00  73.00   0.50    0.50    --  108.75 -61.00-180.00   70
 83  \w     40.00  70.00   0.50    0.50    --  108.75 -77.00-120.00   60
 84  \w    152.00 177.00   0.50    0.50    --  108.75  77.00  90.00   50
 85  \w     81.00 146.00   0.50    0.50    --  108.75  77.00  90.00  130
 86  \w     37.00  71.00   0.50    0.50    --  108.75 -61.00 120.00   68
 87  \w     53.00 105.00   0.50    0.50    --  108.75 -95.00   0.00  104
 88  \w     59.00  85.00   0.50    0.50    --  108.75 -95.00-150.00   52
 89  \w    113.00 147.00   0.50    0.50    --  108.75  77.00 -90.00   68
 90  \w     85.00 110.00   0.50    0.50    --  108.75  77.00 -90.00   50
 91  \w    120.00 174.00   0.50    0.50    --  108.75  30.00  60.00  108
 92  \w     85.00 145.00   0.50    0.50    --  108.75  61.00 -30.00  120
 93  \w     89.00 114.00   0.50    0.50    --  108.75  30.00  60.00   50
 94  \w     95.00 165.00   0.50    0.50    --  108.75  61.00-150.00  140
 95  \w     80.00 178.00   0.50    0.50    --  108.75  77.00 150.00  196
 96  \w     69.00 107.00   0.50    0.50    --  108.75-125.00   0.00   76
 97  \w    126.00 175.00   0.50    0.50    --  108.75  45.00  90.00   98
 98  \w     85.00 135.00   0.50    0.50    --  108.75  61.00-120.00  100
 99  \w     38.00  64.00   0.50    0.50    --  108.75-125.00   0.00   52
100  \w     89.00 115.00   0.50    0.50    --  108.75  45.00  90.00   52
101  \w     40.00 106.00   0.50    0.50    --  108.75 -77.00  60.00  132
102  \w    142.00 178.00   0.50    0.50    --  108.75  77.00  30.00   72
103  \w    141.00 175.00   0.50    0.50    --  108.75  45.00   0.00   68
104  \w     80.00 105.00   0.50    0.50    --  108.75 -95.00 -60.00   50
105  \w     90.00 122.00   0.50    0.50    --  108.75  45.00   0.00   64
106  \w     38.00  74.00   0.50    0.50    --  108.75 -95.00 -60.00   72
107  \w    108.00 171.00   0.50    0.50    --  108.75  77.00-180.00  126
108  \w    143.00 173.00   0.50    0.50    --  108.75  45.00-120.00   60
109  \w     45.00  91.00   0.50    0.50    --  108.75 -77.00  30.00   92
110  \w    127.00 153.00   0.50    0.50    --  108.75  77.00 -60.00   52
111  \w     83.00 115.00   0.50    0.50    --  108.75  77.00 -60.00   64
112  \w     96.00 121.00   0.50    0.50    --  108.75  45.00-120.00   50
113  \w    135.00 161.00   0.50    0.50    --  108.75  77.00  60.00   52
114  \w     95.00 175.00   0.50    0.50    --  108.75  77.00 120.00  160
115  \w     80.00 106.00   0.50    0.50    --  108.75  77.00  60.00   52
116  \w     93.00 167.00   0.50    0.50    --  108.75  45.00 -90.00  148
117  \w     67.00 102.00   0.50    0.50    --  108.75 -95.00-120.00   70
118  \w     84.00 137.00   0.50    0.50    --  108.75  77.00  30.00  106
;
_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      0.1191121000
_diffrn_orient_matrix_UB_12      -0.1523191000
_diffrn_orient_matrix_UB_13      -0.0000904000
_diffrn_orient_matrix_UB_21      -0.0069407000
_diffrn_orient_matrix_UB_22      -0.0036612000
_diffrn_orient_matrix_UB_23      -0.0721654000
_diffrn_orient_matrix_UB_31      0.1807540000
_diffrn_orient_matrix_UB_32      0.1003112000
_diffrn_orient_matrix_UB_33      -0.0027811000
_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  0.0348
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            35155
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.621
_diffrn_reflns_theta_min         4.146
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.27a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1062 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0473P)^2^+0.2464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0773
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2604
_reflns_number_total             2676
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00607c2.cif
_cod_data_source_block           exp_472
_cod_depositor_comments          'Adding full bibliography for 7158649.cif.'
_cod_database_code               7158649
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C15H19N1O1
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.956
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.90
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
_shelx_res_checksum              28842
_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 1.305
_oxdiff_exptl_absorpt_empirical_full_min 0.810