Direct catalytic asymmetric and anti-selective vinylogous addition of butenolides to chromones
Cui, Jin; Kumagai, Naoya; Watanabe, Takumi; Shibasaki, Masakatsu; Chemical Science 11 (2020) 7170–7176; doi:10.1039/D0SC01914C

data_1558393
_publ_section_title
;
 Direct catalytic asymmetric and anti-selective vinylogous addition of
 butenolides to chromones
;
_journal_issue                   27
_journal_name_full               'Chemical Science'
_journal_page_first              7170
_journal_page_last               7176
_journal_paper_doi               10.1039/D0SC01914C
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H11 N O6'
_chemical_formula_sum            'C14 H11 N O6'
_chemical_formula_weight         289.23
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-06 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.099(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4535(2)
_cell_length_b                   6.54820(10)
_cell_length_c                   15.9054(3)
_cell_measurement_reflns_used    9336
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      76.0500
_cell_measurement_theta_min      4.0430
_cell_volume                     1252.28(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_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      93.15
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_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     17.00  42.00   0.50    0.31    --   47.95 -22.00 -92.00   50
  2  \w     37.00 120.00   0.50    0.31    --   47.95  38.00-180.00  166
  3  \w     91.00 122.00   0.50    1.52    --  106.49  61.00-180.00   62
  4  \w     85.00 111.00   0.50    1.52    --  106.49  77.00-180.00   52
  5  \w     31.00  61.00   0.50    1.52    --  106.49 -22.00 -92.00   60
  6  \w     41.00  66.00   0.50    1.52    --  106.49 -45.00-180.00   50
  7  \w     35.00 108.00   0.50    1.52    --  106.49 -94.00-180.00  146
  8  \w     33.00 117.00   0.50    0.31    --   47.95  57.00-120.00  168
  9  \w     36.00  75.00   0.50    1.52    --  106.49 -45.00  30.00   78
 10  \w     33.00  61.00   0.50    1.52    --  106.49 -30.00  90.00   56
 11  \w     32.00  61.00   0.50    1.52    --  106.49 -30.00 120.00   58
 12  \w     33.00  61.00   0.50    1.52    --  106.49 -30.00 150.00   56
 13  \w     35.00  63.00   0.50    1.52    --  106.49 -45.00  90.00   56
 14  \w     60.00  86.00   0.50    1.52    --  106.49 -94.00 150.00   52
 15  \w     63.00  89.00   0.50    0.31    --   47.95  22.00  73.00   52
 16  \w     36.00 121.00   0.50    0.31    --   47.95  38.00  90.00  170
 17  \w    115.00 141.00   0.50    1.52    --  106.49  22.00  73.00   52
 18  \w     87.00 114.00   0.50    1.52    --  106.49  77.00 150.00   54
 19  \w     86.00 112.00   0.50    1.52    --  106.49  77.00  90.00   52
 20  \w     91.00 117.00   0.50    1.52    --  106.49  61.00 150.00   52
 21  \w     25.00  81.00   0.50    0.31    --   47.95  77.00 150.00  112
 22  \w    -60.00  28.00   0.50    0.31    --  -47.95  22.00  73.00  176
 23  \w    -79.00 -54.00   0.50    0.31    --  -47.95 -22.00 -92.00   50
 24  \w    -67.00 -41.00   0.50    0.31    --  -47.95 -77.00-120.00   52
 25  \w   -102.00 -77.00   0.50    1.52    -- -100.00 -77.00-180.00   50
 26  \w   -102.00 -77.00   0.50    1.52    -- -100.00 -76.00-160.13   50
 27  \w   -106.00 -80.00   0.50    1.52    -- -100.00 -75.00-124.52   52
 28  \w   -111.00 -83.00   0.50    1.52    -- -100.00 -62.00-130.48   56
 29  \w   -102.00 -76.00   0.50    1.52    -- -100.00 -81.00-135.28   52
 30  \w   -105.00 -79.00   0.50    1.52    -- -100.00 -74.00-148.73   52
 31  \w   -114.00 -88.00   0.50    1.52    -- -100.00 -64.00-178.67   52
 32  \w   -118.00 -83.00   0.50    1.52    -- -100.00 -61.00-137.40   70
 33  \w   -127.00 -84.00   0.50    1.52    -- -100.00 -61.00-120.00   86
 34  \w   -131.00 -88.00   0.50    1.52    -- -100.00 -22.00 -92.00   86
 35  \w    -63.00 -29.00   0.50    1.52    -- -100.00  30.00 -90.00   68
 36  \w    -95.00 -21.00   0.50    0.31    --  -47.95 125.00-180.00  148
 37  \w   -117.00 -68.00   0.50    1.52    -- -100.00  77.00 -60.00   98
 38  \w    -65.00 -25.00   0.50    1.52    -- -100.00  22.00  73.00   80
 39  \w    -63.00 -25.00   0.50    0.31    --  -47.95 -77.00 150.00   76
 40  \w   -103.00 -77.00   0.50    1.52    -- -100.00 -77.00 150.00   52
 41  \w   -106.00 -80.00   0.50    1.52    -- -100.00 -71.00 159.97   52
 42  \w   -111.00 -85.00   0.50    1.52    -- -100.00 -73.00 159.86   52
 43  \w   -108.00 -82.00   0.50    1.52    -- -100.00 -71.00 137.93   52
 44  \w   -106.00 -80.00   0.50    1.52    -- -100.00 -72.00 171.23   52
 45  \w   -114.00 -87.00   0.50    1.52    -- -100.00 -50.00 174.61   54
 46  \w   -150.00-124.00   0.50    1.52    -- -100.00 -50.00 174.61   52
 47  \w   -166.00 -78.00   0.50    1.52    -- -100.00 -75.00 135.14  176
 48  \w   -170.00 -77.00   0.50    1.52    -- -100.00 -77.00 120.00  186
 49  \w   -166.00 -77.00   0.50    1.52    -- -100.00 -77.00 -90.00  178
 50  \w   -133.00 -83.00   0.50    1.52    -- -100.00 -61.00-150.00  100
 51  \w   -173.00-147.00   0.50    1.52    -- -100.00 -75.00-124.52   52
 52  \w   -173.00-117.00   0.50    1.52    -- -100.00 -76.00-160.13  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-Custom'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0081579000
_diffrn_orient_matrix_UB_12      -0.0669478000
_diffrn_orient_matrix_UB_13      0.0942775000
_diffrn_orient_matrix_UB_21      0.1277627000
_diffrn_orient_matrix_UB_22      0.0116586000
_diffrn_orient_matrix_UB_23      0.0210681000
_diffrn_orient_matrix_UB_31      -0.0041590000
_diffrn_orient_matrix_UB_32      0.2253284000
_diffrn_orient_matrix_UB_33      0.0270439000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18430
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.423
_diffrn_reflns_theta_min         2.878
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    1.042
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1789 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         4850
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0490P)^2^+0.2920P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.869
_reflns_number_gt                4567
_reflns_number_total             4850
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01914c2.cif
_cod_data_source_block           exp_240
_cod_depositor_comments
;
 Adding full bibliography for 1558392--1558393.cif.

2022-05-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C14 H11 N O6)'
_cod_original_formula_sum        'C28 H22 N2 O12'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     578.47
_cod_database_code               1558393
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     Jin
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.903
_reflns_odcompleteness_completeness 99.96
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00U(H00U), C00X(H00X)
2.b Secondary CH2 refined with riding coordinates:
 C012(H01f,H01g), C014(H01a,H01b)
2.c Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00L(H00L), C00M(H00M), C00N(H00N), C00S(H00S),
 C00V(H00V), C00Y(H00Y), C00Z(H00Z), C011(H011)
2.d Idealised Me refined as rotating group:
 C015(H01c,H01d,H01e), C016(H01h,H01i,H01j)
;
_shelx_res_checksum              12608
_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 1.236
_oxdiff_exptl_absorpt_empirical_full_min 0.641