The seven-step, one-pot regioselective synthesis of biologically important 3-aryllawsones: scope and applications.
Krishna, Anugam V.; Ramachary, Dhevalapally B.; Organic & biomolecular chemistry 20 (2022) 3948–3954; doi:10.1039/d2ob00438k

data_7158577
_publ_section_title
;
 The seven-step, one-pot regioselective synthesis of biologically
 important 3-aryllawsones: scope and applications.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3948
_journal_page_last               3954
_journal_paper_doi               10.1039/d2ob00438k
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C17 H12 O4'
_chemical_formula_sum            'C17 H12 O4'
_chemical_formula_weight         280.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-17
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2021-12-09 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.455(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4584(4)
_cell_length_b                   3.9248(2)
_cell_length_c                   31.2078(13)
_cell_measurement_reflns_used    3769
_cell_measurement_temperature    298.0(7)
_cell_measurement_theta_max      26.5150
_cell_measurement_theta_min      2.4480
_cell_volume                     1275.19(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (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_environment      air
_diffrn_ambient_temperature      298.0(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.953
_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    -10.00  89.00   0.50   10.08    --   16.22  30.00 -30.00  198
  2  \w     67.00  92.00   0.50   10.08    --   16.22   8.00 -56.00   50
  3  \w     41.00  66.00   0.50   10.08    --  -14.97   8.00 -56.00   50
  4  \w     -5.00  33.00   0.50   10.08    --   16.22   8.00 -56.00   76
  5  \w    -40.00  -8.00   0.50   10.08    --  -14.97   8.00 -56.00   64
  6  \w     17.00  68.00   0.50   10.08    --   16.22-125.00   0.00  102
  7  \w    -52.00 -13.00   0.50   10.08    --   16.22   8.00 -56.00   78
  8  \w    -36.00  20.00   0.50   10.08    --  -14.97 -94.00-120.00  112
  9  \w    -36.00  38.00   0.50   10.08    --   16.22 -94.00-150.00  148
 10  \w    -66.00 -39.00   0.50   10.08    --  -14.97 125.00-180.00   54
 11  \w    -55.00 -28.00   0.50   10.08    --  -14.97 125.00-150.00   54
 12  \w    -80.00   6.00   0.50   10.08    --  -14.97 -30.00 120.00  172
 13  \w     -9.00  16.00   0.50   10.08    --   16.22  -8.00 128.00   50
 14  \w    -40.00 -15.00   0.50   10.08    --  -14.97  -8.00 128.00   50
 15  \w    -44.00 -19.00   0.50   10.08    --  -14.97 -61.00 120.00   50
 16  \w    -72.00 -47.00   0.50   10.08    --  -14.97 -61.00 120.00   50
 17  \w    -52.00 -25.00   0.50   10.08    --  -14.97 125.00 120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0398719000
_diffrn_orient_matrix_UB_12      -0.0268364000
_diffrn_orient_matrix_UB_13      0.0193845000
_diffrn_orient_matrix_UB_21      -0.0552007000
_diffrn_orient_matrix_UB_22      -0.0121278000
_diffrn_orient_matrix_UB_23      0.0114710000
_diffrn_orient_matrix_UB_31      -0.0022399000
_diffrn_orient_matrix_UB_32      -0.1783697000
_diffrn_orient_matrix_UB_33      -0.0036815000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            9480
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.937
_diffrn_reflns_theta_min         1.956
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0493
_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^)+(0.0735P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1474
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1741
_reflns_number_total             2604
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00438k4.cif
_cod_data_source_block           dbr23
_cod_depositor_comments
'Adding full bibliography for 7158576--7158579.cif.'
_cod_database_code               7158577
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.979
_reflns_odcompleteness_completeness 99.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13), C5(H5), C1(H1), C14(H14), C2(H2), C4(H4), C3(H3A)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              31831
_olex2_submission_original_sample_id DBR23
_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 3.614
_oxdiff_exptl_absorpt_empirical_full_min 0.353