One-Pot Synthesis of 4-Carboalkoxy-Substituted Benzo[h]coumarins from α- and β-Naphthols and Their Excited-State Properties
Chandra, Ajeet; Jana, Kanyashree; Moorthy, Jarugu Narasimha; ACS Omega  (2019) –; doi:10.1021/acsomega.9b02489

data_4517279
_publ_section_title
;
 One-Pot Synthesis of 4-Carboalkoxy-Substituted Benzo[h]coumarins from \a-
 and \b-Naphthols and Their Excited-State Properties
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.9b02489
_journal_year                    2019
_chemical_formula_moiety         'C16 H12 O4'
_chemical_formula_sum            'C16 H12 O4'
_chemical_formula_weight         268.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                63.671(5)
_cell_angle_beta                 84.888(6)
_cell_angle_gamma                87.848(6)
_cell_formula_units_Z            2
_cell_length_a                   6.5821(14)
_cell_length_b                   10.142(2)
_cell_length_c                   10.290(2)
_cell_measurement_reflns_used    3583
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.24
_cell_volume                     613.2(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9987
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9426
_diffrn_reflns_theta_full        28.3663
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         2.35
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4528
_exptl_crystal_description       block
_exptl_crystal_F_000             280.1721
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.4198
_refine_diff_density_min         -0.4607
_refine_diff_density_rms         0.1094
_refine_ls_d_res_high            0.7480
_refine_ls_d_res_low             8.6545
_refine_ls_goodness_of_fit_ref   1.0734
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0734
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0684P)^2^+0.0762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1370
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2236
_reflns_number_total             3072
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ao9b02489_si_002.cif
_cod_data_source_block           16nova_0m
_cod_database_code               4517279
_olex2_refinement_description
;
1. 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
2.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C17(H17), C20(H20), C19(H19), C18(H18), C7(H7)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_olex2_submission_special_instructions 'No special instructions were received'