Synthesis of 7-hydroxydibenzopyran-6-ones via benzannulation of coumarins
Surya Prakash Rao, H.; Prabakaran, M.; Muthanna, Nandurka; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01203K

data_7158826
_publ_section_title
;
 Synthesis of 7-hydroxydibenzopyran-6-ones via benzannulation of coumarins
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01203K
_journal_year                    2022
_chemical_formula_moiety         'C15 H6 F3 N O6 S'
_chemical_formula_sum            'C15 H6 F3 N O6 S'
_chemical_formula_weight         385.27
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-12-18
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2022-05-24 deposited with the CCDC.	2022-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                102.129(4)
_cell_angle_beta                 104.972(5)
_cell_angle_gamma                94.329(5)
_cell_formula_units_Z            2
_cell_length_a                   6.6654(4)
_cell_length_b                   9.6240(5)
_cell_length_c                   12.5534(7)
_cell_measurement_reflns_used    4814
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2809
_cell_measurement_theta_min      3.1694
_cell_volume                     753.36(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9838
_diffrn_measurement_details
;
  1 omega   18.00   52.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272   57.0000   60.0000 34

  2 omega   -9.00   90.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397   77.0000 -180.0000 99

  3 omega   -4.00   25.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397   81.0000  -69.0000 29

  4 omega  -53.00   39.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397  -37.0000  -90.0000 92

  5 omega  -25.00   62.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397  -99.0000   60.0000 87

  6 omega  -86.00    4.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -57.0000  -90.0000 90

  7 omega  -25.00   25.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000   60.0000 50

  8 omega  -38.00   52.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272   57.0000   30.0000 90

  9 omega   32.00   96.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397 -178.0000  150.0000 64

 10 omega  -50.00   50.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397  -77.0000  -90.0000 100

 11 omega  -25.00   62.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397  -99.0000  150.0000 87

 12 omega   35.00   96.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397  178.0000  -90.0000 61

 13 omega   -6.00   92.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397   37.0000   60.0000 98

 14 omega   -2.00   71.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       19.8397   57.0000  150.0000 73
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0511624000
_diffrn_orient_matrix_UB_12      0.0500809000
_diffrn_orient_matrix_UB_13      0.0297573000
_diffrn_orient_matrix_UB_21      -0.0982558000
_diffrn_orient_matrix_UB_22      -0.0332682000
_diffrn_orient_matrix_UB_23      -0.0382272000
_diffrn_orient_matrix_UB_31      -0.0097780000
_diffrn_orient_matrix_UB_32      -0.0466612000
_diffrn_orient_matrix_UB_33      0.0357790000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16636
_diffrn_reflns_theta_full        29.35
_diffrn_reflns_theta_max         29.35
_diffrn_reflns_theta_min         3.18
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0690P)^2^+0.3181P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1408
_reflns_number_gt                2850
_reflns_number_total             3703
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ob01203k2.cif
_cod_data_source_block           17i
_cod_original_cell_volume        753.35(7)
_cod_database_code               7158826
_chemical_oxdiff_formula         'C15 H6 F3 N O6 S'
_chemical_oxdiff_usercomment     'COLOURLESS PLATE , 298K,0.62 0.38 0.08'
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32