Facile Synthesis of Azaarene-Substituted Hydroxycoumarins Possessing High Biological Activities via Three-Component C(sp(3))-H Functionalization.
Dong, Haoxun; Xu, Lubin; Li, Shuai-Shuai; Wang, Liang; Shao, Chang-Lun; Xiao, Jian; ACS combinatorial science 18 (2016) 604–610; doi:10.1021/acscombsci.6b00082

data_4513937
_publ_section_title
;
 Facile Synthesis of Azaarene-Substituted Hydroxycoumarins Possessing High
 Biological Activities via Three-Component C(sp(3))-H Functionalization.
;
_journal_issue                   9
_journal_name_full               'ACS combinatorial science'
_journal_page_first              604
_journal_page_last               610
_journal_paper_doi               10.1021/acscombsci.6b00082
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C25 H18 O3'
_chemical_formula_weight         366.39
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 99.420(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3780(10)
_cell_length_b                   9.4460(7)
_cell_length_c                   15.0710(11)
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      72.40
_cell_measurement_theta_min      3.35
_cell_volume                     1878.8(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32398
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.430
_diffrn_reflns_theta_min         3.349
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.598
_exptl_crystal_size_mid          0.577
_exptl_crystal_size_min          0.490
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0094(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0644P)^2^+0.4027P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3496
_reflns_number_total             3707
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            co6b00082_si_003.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 4513937.cif.'
_cod_database_code               4513937
_shelx_estimated_absorpt_t_min   0.688
_shelx_estimated_absorpt_t_max   0.733
_shelxl_version_number           2013-4
_shelx_res_checksum              19705
_shelx_hkl_checksum              71625