Synthesis of Quinolinones with Palladium-Catalyzed Oxidative Annulation between Acrylamides and Arynes.
Wang, Weiguo; Peng, Xianglong; Qin, Xiaoyu; Zhao, Xiangyun; Ma, Chen; Tung, Chen-Ho; Xu, Zhenghu; The Journal of organic chemistry 80 (2015) 2835–2841; doi:10.1021/jo5027673

data_4030726
_publ_section_title
;
 Synthesis of Quinolinones with Palladium-Catalyzed Oxidative Annulation
 between Acrylamides and Arynes.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2835
_journal_page_last               2841
_journal_paper_doi               10.1021/jo5027673
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C16 H13 N O2'
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.917(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.3004(4)
_cell_length_b                   21.1079(9)
_cell_length_c                   14.7263(6)
_cell_measurement_reflns_used    3874
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.897
_cell_measurement_theta_min      3.660
_cell_volume                     2579.8(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.882
_diffrn_measured_fraction_theta_max 0.967
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0914
_diffrn_reflns_Laue_measured_fraction_full 0.882
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17775
_diffrn_reflns_point_group_measured_fraction_full 0.807
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         63.685
_diffrn_reflns_theta_min         3.660
_exptl_absorpt_coefficient_mu    0.691
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Flack x determined using 1799 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.6(4)
_refine_ls_extinction_coef       0.0009(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   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     690
_refine_ls_number_reflns         7533
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1285
_refine_ls_R_factor_gt           0.0976
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2486
_refine_ls_wR_factor_ref         0.2936
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.727
_reflns_Friedel_fraction_max     0.800
_reflns_number_gt                5161
_reflns_number_total             7533
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5027673_si_002.cif
_cod_data_source_block           test
_cod_depositor_comments          'Adding full bibliography for 4030726.cif.'
_cod_database_code               4030726
_shelxl_version_number           2013-4
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24), C28(H28),
  C29(H29), C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36),
 C37(H37), C40(H40), C44(H44), C45(H45), C46(H46), C47(H47), C48(H48), C50(H50),
  C51(H51), C52(H52), C53(H53), C56(H56), C60(H60), C61(H61), C62(H62),
 C63(H63), C64(H64)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C17(H17A,H17B,H17C), C33(H33A,H33B,H33C), C49(H49A,H49B,H49C)
;
_olex2_submission_special_instructions 'No special instructions were received'