Systematic Diversity-Oriented Synthesis of Reduced Flavones from γ-Pyrones to Probe Biological Performance Diversity.
Gerlach, Erica M.; Korkmaz, Melissa A.; Pavlinov, Ivan; Gao, Qiwen; Aldrich, Leslie N.; ACS chemical biology 14 (2019) 1536–1545; doi:10.1021/acschembio.9b00294

data_4514610
_publ_section_title
;
 Systematic Diversity-Oriented Synthesis of Reduced Flavones from
 \g-Pyrones to Probe Biological Performance Diversity.
;
_journal_issue                   7
_journal_name_full               'ACS chemical biology'
_journal_page_first              1536
_journal_page_last               1545
_journal_paper_doi               10.1021/acschembio.9b00294
_journal_volume                  14
_journal_year                    2019
_chemical_formula_sum            'C25 H29 N O8'
_chemical_formula_weight         471.49
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.20
_cell_angle_beta                 82.66
_cell_angle_gamma                78.95
_cell_formula_units_Z            2
_cell_length_a                   6.072
_cell_length_b                   13.299
_cell_length_c                   16.147
_cell_measurement_reflns_used    6318
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.7464
_cell_measurement_theta_min      2.3453
_cell_volume                     1221.463
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_sigmaI/netI    0.0844
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23488
_diffrn_reflns_theta_full        23.92
_diffrn_reflns_theta_max         23.92
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_correction_T_min  0.9627
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.027(8)
_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   1.558
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         3757
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.570
_refine_ls_R_factor_all          0.1885
_refine_ls_R_factor_gt           0.1087
_refine_ls_shift/su_max          3.194
_refine_ls_shift/su_mean         0.077
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2489
_refine_ls_wR_factor_ref         0.2746
_reflns_number_gt                2163
_reflns_number_total             3757
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cb9b00294_si_001.cif
_cod_data_source_block           Compound_9i_2
_cod_original_cell_volume        1221.6
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4514610