Cu(II)-catalyzed coupling of aromatic C-H bonds with malonates.
Wang, Hong-Li; Shang, Ming; Sun, Shang-Zheng; Zhou, Zeng-Le; Laforteza, Brian N.; Dai, Hui-Xiong; Yu, Jin-Quan; Organic letters 17 (2015) 1228–1231; doi:10.1021/acs.orglett.5b00193

data_1554806
_publ_section_title
;
 Cu(II)-catalyzed coupling of aromatic C-H bonds with malonates.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1228
_journal_page_last               1231
_journal_paper_doi               10.1021/acs.orglett.5b00193
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C13 H12 O4'
_chemical_formula_weight         232.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 95.216(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
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_cell_length_b                   14.0223(15)
_cell_length_c                   15.5670(17)
_cell_measurement_reflns_used    3381
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.791
_cell_measurement_theta_min      4.847
_cell_volume                     2291.4(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
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_computing_molecular_graphics    'Bruker SHELXTL'
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_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
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_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.958
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.288
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_refine_ls_extinction_coef       0.0105(17)
_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   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0625
_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^)+(0.1047P)^2^+0.3280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1640
_refine_ls_wR_factor_ref         0.1820
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3117
_reflns_number_total             4497
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00193_si_002.cif
_cod_data_source_block           cd214425
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1554806
_shelxl_version_number           2013-4
_shelx_res_checksum              42654
_shelx_hkl_checksum              39430