Pd(ii)-Catalyzed C8-H alkoxycarbonylmethylation of 1-naphthylamides with α-chloroalkyl esters.
Wang, Xiaolong; Feng, Cancan; Yang, Fan; Wu, Yangjie; Organic & biomolecular chemistry 17 (2019) 4865–4868; doi:10.1039/c9ob00648f

data_7156803
_publ_section_title
;
 Pd(ii)-Catalyzed C8-H alkoxycarbonylmethylation of 1-naphthylamides with
 \a-chloroalkyl esters.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4865
_journal_page_last               4868
_journal_paper_doi               10.1039/c9ob00648f
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C19 H16 N2 O3'
_chemical_formula_weight         320.34
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-03-06 deposited with the CCDC.    2019-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   7.6372(6)
_cell_length_b                   7.6372(6)
_cell_length_c                   23.721(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1198.21(17)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8281
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.994
_diffrn_reflns_theta_min         5.595
_exptl_absorpt_coefficient_mu    0.745
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1060 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(18)
_refine_ls_extinction_coef       0.0129(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2965
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0512P)^2^+0.1434P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1119
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                2595
_reflns_number_total             2965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00648f2.cif
_cod_data_source_block           2018114670
_cod_depositor_comments          'Adding full bibliography for 7156803.cif.'
_cod_original_cell_volume        1198.2(2)
_cod_database_code               7156803
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.853
_shelx_estimated_absorpt_t_max   0.903
_shelx_res_checksum              30712