Regioselective palladium-catalyzed decarboxylative cross-coupling reaction of alkenyl acids with coumarins: synthesis of 3-styrylcoumarin compounds.
Wang, Xu; Li, Shen-Yan; Pan, Ying-Ming; Wang, Heng-Shan; Chen, Zhen-Feng; Huang, Ke-Bin; The Journal of organic chemistry 80 (2015) 2407–2412; doi:10.1021/jo502572j

data_4030579
_publ_section_title
;
 Regioselective palladium-catalyzed decarboxylative cross-coupling
 reaction of alkenyl acids with coumarins: synthesis of 3-styrylcoumarin
 compounds.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2407
_journal_page_last               2412
_journal_paper_doi               10.1021/jo502572j
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C19 H16 O2'
_chemical_formula_sum            'C19 H16 O2'
_chemical_formula_weight         276.34
_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_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_date             2014-09-15
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 128.85(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.518(10)
_cell_length_b                   6.084(4)
_cell_length_c                   20.729(10)
_cell_measurement_temperature    296.15
_cell_volume                     1425.9(16)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9714
_diffrn_measured_fraction_theta_max 0.9714
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
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_diffrn_reflns_theta_full        30.2713
_diffrn_reflns_theta_max         30.27
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_exptl_absorpt_coefficient_mu    0.082
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
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_exptl_crystal_description       block
_exptl_crystal_F_000             584.3160
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_refine_diff_density_min         -0.3458
_refine_diff_density_rms         0.0684
_refine_ls_d_res_high            0.7050
_refine_ls_d_res_low             11.3065
_refine_ls_goodness_of_fit_ref   1.0792
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     189
_refine_ls_number_reflns         4149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0792
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0632
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1152P)^2^+0.2713P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.2284
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_reflns_limit_h_max              15
_reflns_limit_h_min              -20
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                2559
_reflns_number_total             4149
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo502572j_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 4030579.cif.'
_cod_database_code               4030579
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C20(H20a,H20b,H20c), C21(H21a,H21b,H21c)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C17(H17),
 C18(H18), C19(H19)
;
_olex2_submission_special_instructions 'No special instructions were received'