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_7158825
_publ_section_title
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 Synthesis of 7-hydroxydibenzopyran-6-ones via benzannulation of coumarins
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_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01203K
_journal_year                    2022
_chemical_formula_moiety         'C23 H19 N O5'
_chemical_formula_sum            'C23 H19 N O5'
_chemical_formula_weight         389.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2b8rhw
_audit_creation_method           SHELXL-2018/3
_audit_update_record
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2022-02-19 deposited with the CCDC.	2022-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.946(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7089(8)
_cell_length_b                   14.3510(12)
_cell_length_c                   14.2749(15)
_cell_measurement_reflns_used    2883
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1084
_cell_measurement_theta_min      2.9845
_cell_volume                     1902.6(3)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2020) and
Mercury
(Macrae <i>et al.</i>,  2020)
;
_computing_publication_material
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ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2020) and
Mercury
(Macrae <i>et al.</i>,  2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10689
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.173
_diffrn_reflns_theta_min         2.991
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysalisPro (Agilent, 2014)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1567
_reflns_number_gt                3119
_reflns_number_total             4413
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01203k2.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158825
_publcif_datablock.id            {29721a57-5e2d-4f3f-a1af-48c4ccae498a}
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              37732
_shelx_hkl_checksum              47255
_publcif_funding_html
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