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_7158578
_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         'C18 H14 O4'
_chemical_formula_sum            'C18 H14 O4'
_chemical_formula_weight         294.29
_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   geom
_audit_creation_date             2021-07-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-09 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                71.516(13)
_cell_angle_beta                 87.083(9)
_cell_angle_gamma                75.865(10)
_cell_formula_units_Z            2
_cell_length_a                   5.4420(5)
_cell_length_b                   10.6713(15)
_cell_length_c                   12.7912(18)
_cell_measurement_reflns_used    2237
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      24.4020
_cell_measurement_theta_min      2.0670
_cell_volume                     682.89(16)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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    -37.00  17.00   0.50   12.00    --  -15.60 -94.00 -60.00  108
  2  \w     19.00  44.00   0.50   12.00    --   16.22-130.00 -34.00   50
  3  \w    -28.00  -2.00   0.50   12.00    --  -15.60 -30.00 -90.00   52
  4  \w    -15.00  40.00   0.50   12.00    --   16.22 -30.00 -90.00  110
  5  \w     57.00  88.00   0.50   12.00    --   16.22  30.00-120.00   62
  6  \w      8.00  43.00   0.50   12.00    --   16.22  30.00-120.00   70
  7  \w    -30.00  21.00   0.50   12.00    --  -15.60 -94.00 -30.00  102
  8  \w    -56.00 -22.00   0.50   12.00    --   16.22 -30.00 -90.00   68
  9  \w    -86.00 -45.00   0.50   12.00    --  -15.60 -30.00 -90.00   82
 10  \w    -87.00 -49.00   0.50   12.00    --  -15.60 -30.00   0.00   76
 11  \w      6.00  32.00   0.50   12.00    --   16.22 -30.00  60.00   52
 12  \w     -7.00  86.00   0.50   12.00    --   16.22  45.00  90.00  186
 13  \w     49.00  75.00   0.50   12.00    --   16.22  45.00 120.00   52
 14  \w     10.00  35.00   0.50   12.00    --   16.22  45.00 120.00   50
 15  \w    -43.00 -18.00   0.50   12.00    --  -15.60 130.00  37.00   50
 16  \w    -55.00 -29.00   0.50   12.00    --   16.22 -30.00  60.00   52
 17  \w    -37.00 -11.00   0.50   12.00    --   16.22 -94.00  90.00   52
 18  \w     47.00  75.00   0.50   12.00    --   16.22-139.00 150.00   56
 19  \w    -37.00  21.00   0.50   12.00    --  -15.60 -94.00 150.00  116
 20  \w    -85.00  16.00   0.50   12.00    --  -15.60 -77.00 150.00  202
 21  \w    -65.00 -17.00   0.50   12.00    --  -15.60 139.00-148.00   96
 22  \w    -46.00  36.00   0.50   12.00    --   16.22 -45.00-180.00  164
;
_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      0.0007871000
_diffrn_orient_matrix_UB_12      0.0192100000
_diffrn_orient_matrix_UB_13      -0.0584023000
_diffrn_orient_matrix_UB_21      0.0067740000
_diffrn_orient_matrix_UB_22      0.0664032000
_diffrn_orient_matrix_UB_23      -0.0024336000
_diffrn_orient_matrix_UB_31      0.1342894000
_diffrn_orient_matrix_UB_32      -0.0208714000
_diffrn_orient_matrix_UB_33      0.0021548000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1054
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2382
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26414
_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 yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2382
_refine_ls_number_restraints     76
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0775
_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^)+(0.1013P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1854
_refine_ls_wR_factor_ref         0.2290
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1280
_reflns_number_total             2382
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00438k4.cif
_cod_data_source_block           dbr29a
_cod_depositor_comments
'Adding full bibliography for 7158576--7158579.cif.'
_cod_database_code               7158578
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.980
_reflns_odcompleteness_completeness 97.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.861(4)
 0.139(4)
2. 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, All O(H) groups
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.34A with sigma of 0.04 and
sigma for terminal atoms of 0.08
All non-hydrogen atoms have similar U: within 1.34A with sigma of 0.04 and
sigma for terminal atoms of 0.08
5.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4A), C7(H7), C3(H3), C14(H14), C15(H15), C18(H18), C16(H16), C17(H17)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
5.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              85948
_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 5.762
_oxdiff_exptl_absorpt_empirical_full_min 0.281