Radical 5-exo cyclization of alkynoates with 2-oxoacetic acids for synthesis of 3-acylcoumarins
Liu, Tong; Ding, Qiuping; Zong, Qianshou; Qiu, Guanyinsheng; Organic Chemistry Frontiers 2 (2015) 670–; doi:10.1039/C5QO00029G

data_1553100
_publ_section_title
;
 Radical 5-exo cyclization of alkynoates with 2-oxoacetic acids for
 synthesis of 3-acylcoumarins
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              670
_journal_paper_doi               10.1039/C5QO00029G
_journal_volume                  2
_journal_year                    2015
_chemical_formula_sum            'C23 H16 O3.19'
_chemical_formula_weight         343.36
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-01-12 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.849(3)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   22.264(4)
_cell_length_b                   10.1945(18)
_cell_length_c                   30.920(5)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.66
_cell_measurement_theta_min      2.30
_cell_volume                     7014(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      193(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            46412
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.667
_diffrn_reflns_theta_min         1.318
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             2872
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     989
_refine_ls_number_reflns         14693
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.0885P)^2^+4.5409P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1916
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9613
_reflns_number_total             14693
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00029g2.cif
_cod_data_source_block           mo_41110a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1553100
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.975
_shelxl_version_number           2013-2
_shelx_res_checksum              67782
_shelx_hkl_checksum              62207