Asymmetric Michael reaction of 3-homoacyl coumarins with chromone-fused dienes toward enantioenriched coumarin chromone skeletons.
Yan, Juzhang; Zheng, Xiurong; Zheng, Yangqing; Zhan, Ruoting; Huang, Huicai; Organic & biomolecular chemistry 19 (2021) 8102–8107; doi:10.1039/d1ob01200b

data_7158287
_publ_section_title
;
 Asymmetric Michael reaction of 3-homoacyl coumarins with chromone-fused
 dienes toward enantioenriched coumarin chromone skeletons.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8102
_journal_page_last               8107
_journal_paper_doi               10.1039/d1ob01200b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C35 H23 Br O6'
_chemical_formula_sum            'C35 H23 Br O6'
_chemical_formula_weight         619.44
_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
_audit_creation_date             2021-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-01 deposited with the CCDC.	2021-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.59045(5)
_cell_length_b                   19.69096(12)
_cell_length_c                   23.49012(17)
_cell_measurement_reflns_used    33520
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3730
_cell_measurement_theta_min      2.9190
_cell_volume                     3048.37(4)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.962
_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     83.00 145.00   0.50    0.20    --  106.06  77.00  30.00  124
  2  \w    150.00 176.00   0.50    0.20    --  106.06  77.00  30.00   52
  3  \w    111.00 178.00   0.50    0.20    --  106.06  45.00-180.00  134
  4  \w     31.00 105.00   0.50    0.05    --   45.87  77.00-120.00  148
  5  \w    -28.00  12.00   0.50    0.05    --   45.87 -19.00 -90.00   80
  6  \w     80.00 108.00   0.50    0.20    --  106.06 -77.00 -90.00   56
  7  \w     37.00  99.00   0.50    0.20    --  106.06 -77.00-120.00  124
  8  \w     44.00  73.00   0.50    0.20    --  106.06 -61.00 -90.00   58
  9  \w     45.00  70.00   0.50    0.20    --  106.06 -77.00 -90.00   50
 10  \w     33.00  72.00   0.50    0.20    --  106.06 -61.00  30.00   78
 11  \w     81.00 108.00   0.50    0.20    --  106.06 -77.00  60.00   54
 12  \w     33.00  73.00   0.50    0.20    --  106.06 -61.00 120.00   80
 13  \w     33.00  72.00   0.50    0.20    --  106.06 -61.00  60.00   78
 14  \w    -26.00  29.00   0.50    0.05    --   45.87 -19.00 -60.00  110
 15  \w     33.00  67.00   0.50    0.20    --  106.06 -94.00-120.00   68
 16  \w     44.00 119.00   0.50    0.20    --  106.06-135.00-100.00  150
 17  \w     45.00  99.00   0.50    0.05    --   45.87-135.00-100.00  108
 18  \w     92.00 117.00   0.50    0.20    --  106.06-133.00  78.00   50
 19  \w     38.00  86.00   0.50    0.20    --  106.06-133.00  78.00   96
 20  \w     56.00  83.00   0.50    0.20    --  106.06 -94.00 150.00   54
 21  \w     49.00  76.00   0.50    0.05    --   45.87-133.00  78.00   54
 22  \w     81.00 106.00   0.50    0.20    --  106.06 -94.00-150.00   50
 23  \w    -24.00  30.00   0.50    0.05    --  -45.87  19.00 -30.00  108
 24  \w    -25.00  15.00   0.50    0.05    --  -45.87  19.00 -60.00   80
 25  \w    -80.00 -54.00   0.50    0.05    --  -45.87 135.00 -34.00   52
 26  \w    -98.00 -25.00   0.50    0.05    --  -45.87 133.00 146.00  146
 27  \w   -110.00 -30.00   0.50    0.20    -- -102.00 133.00 146.00  160
 28  \w   -104.00 -31.00   0.50    0.20    -- -102.00  77.00 150.00  146
 29  \w   -108.00 -65.00   0.50    0.20    -- -102.00 135.00 -34.00   86
 30  \w    -62.00 -29.00   0.50    0.20    -- -102.00 135.00 -34.00   66
 31  \w     72.00 111.00   0.50    0.05    --   45.87 135.00 -34.00   78
 32  \w     89.00 119.00   0.50    0.05    --   45.87 133.00 146.00   60
 33  \w    101.00 126.00   0.50    0.20    --  106.06 133.00 146.00   50
 34  \w    101.00 126.00   0.50    0.20    --  106.06 135.00 -34.00   50
 35  \w   -106.00 -81.00   0.50    0.05    --  -45.87-125.00-150.00   50
 36  \w   -118.00 -73.00   0.50    0.05    --  -45.87-135.00-100.00   90
 37  \w   -171.00 -84.00   0.50    0.20    -- -102.00 -94.00-150.00  174
 38  \w   -122.00 -97.00   0.50    0.20    -- -102.00-135.00-100.00   50
 39  \w   -117.00 -92.00   0.50    0.05    --  -45.87-133.00  78.00   50
 40  \w   -146.00-121.00   0.50    0.20    -- -102.00-133.00  78.00   50
 41  \w   -147.00 -84.00   0.50    0.20    -- -102.00 -94.00  30.00  126
 42  \w   -175.00-113.00   0.50    0.20    -- -102.00 -77.00   0.00  124
 43  \w   -172.00-146.00   0.50    0.20    -- -102.00 -45.00  90.00   52
 44  \w   -171.00-126.00   0.50    0.20    -- -102.00 -15.00 120.00   90
 45  \w   -121.00 -87.00   0.50    0.20    -- -102.00 -45.00  90.00   68
 46  \w   -166.00 -91.00   0.50    0.20    -- -102.00 -15.00 -90.00  150
;
_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      0.0017040000
_diffrn_orient_matrix_UB_12      0.0723190000
_diffrn_orient_matrix_UB_13      -0.0249537000
_diffrn_orient_matrix_UB_21      0.0031174000
_diffrn_orient_matrix_UB_22      0.0298075000
_diffrn_orient_matrix_UB_23      0.0606376000
_diffrn_orient_matrix_UB_31      0.2337958000
_diffrn_orient_matrix_UB_32      -0.0009176000
_diffrn_orient_matrix_UB_33      -0.0005734000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            41075
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.776
_diffrn_reflns_theta_min         3.763
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72029
_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    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.499
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Flack x determined using 5030 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.023(6)
_refine_ls_extinction_coef       0.00045(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     758
_refine_ls_number_reflns         11891
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0800P)^2^+2.5132P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1293
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.886
_reflns_number_gt                11475
_reflns_number_total             11891
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01200b2.cif
_cod_data_source_block           jz05_2
_cod_depositor_comments          'Adding full bibliography for 7158287.cif.'
_cod_original_cell_volume        3048.36(4)
_cod_database_code               7158287
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C O H Br'
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.917
_diffrn_oxdiff_digest_frames
;
013205c634a3c1d56c992218784f66e428000960ae6
;
_diffrn_oxdiff_digest_hkl
;
017218c9d470fce899aa5b7cd51b8ed98de8d6
;
_reflns_odcompleteness_completeness 99.98
_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
2.a Ternary CH refined with riding coordinates:
 C13(H13), C10(H10), C48(H48), C45(H45)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C46(H46A,H46B)
2.c Aromatic/amide H refined with riding coordinates:
 C54(H54), C35(H35), C52(H52), C70(H70), C8(H8), C60(H60), C31(H31), C5(H5),
 C55(H55), C36(H36), C34(H34), C40(H40), C43(H43), C27(H27), C41(H41), C21(H21),
  C25(H25), C33(H33), C57(H57), C69(H69), C1(H1), C6(H6), C28(H28), C29(H29),
 C32(H32), C26(H26), C64(H64), C16(H16), C56(H56), C66(H66), C63(H63), C19(H19),
  C61(H61), C67(H67), C17(H17), C68(H68), C18(H18), C62(H62)
;
_shelx_res_checksum              7089
_shelx_hkl_checksum              93504
_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 1.583
_oxdiff_exptl_absorpt_empirical_full_min 0.652