Synthesis of 3-(2-Olefinbenzyl)-4H-chromen-4-one through Cyclobenzylation and Catalytic C-H Bond Functionalization Using Palladium(II).
Lin, Yu-Feng; Fong, Chi; Peng, Wan-Ling; Tang, Kuei-Chien; Liang, Yi-En; Li, Wen-Tai; The Journal of organic chemistry 82 (2017) 10855–10865; doi:10.1021/acs.joc.7b01626

data_4032932
_publ_section_title
;
 Synthesis of 3-(2-Olefinbenzyl)-4H-chromen-4-one through Cyclobenzylation
 and Catalytic C-H Bond Functionalization Using Palladium(II).
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10855
_journal_page_last               10865
_journal_paper_doi               10.1021/acs.joc.7b01626
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C24 H23 O8.5'
_chemical_formula_weight         447.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.656(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.0786(4)
_cell_length_b                   13.1662(4)
_cell_length_c                   12.1197(4)
_cell_measurement_reflns_used    4242
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      77.3150
_cell_measurement_theta_min      4.6350
_cell_volume                     2191.94(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.2496
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9723
_diffrn_reflns_theta_full        67.99
_diffrn_reflns_theta_max         67.99
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.868
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             940
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1124P)^2^+0.6216P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1652
_refine_ls_wR_factor_ref         0.1831
_reflns_number_gt                3078
_reflns_number_total             3995
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01626_si_002.cif
_cod_data_source_block           ic18278
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032932.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_original_formula_sum        'C24 H23 O8.50'
_cod_database_code               4032932