Auxiliary-enabled Pd-catalyzed direct arylation of methylene C(sp3)-H bond of cyclopropanes: highly diastereoselective assembling of di- and trisubstituted cyclopropanecarboxamides.
Parella, Ramarao; Gopalakrishnan, Bojan; Babu, Srinivasarao Arulananda; Organic letters 15 (2013) 3238–3241; doi:10.1021/ol4012212

data_1556175
_publ_section_title
;
 Auxiliary-enabled Pd-catalyzed direct arylation of methylene C(sp3)-H
 bond of cyclopropanes: highly diastereoselective assembling of di- and
 trisubstituted cyclopropanecarboxamides.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3238
_journal_page_last               3241
_journal_paper_doi               10.1021/ol4012212
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C17 H16 N2 O3 S'
_chemical_formula_sum            'C17 H16 N2 O3 S'
_chemical_formula_weight         328.39
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-19T11:59:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.12
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.587(3)
_cell_length_b                   8.748(2)
_cell_length_c                   14.954(3)
_cell_measurement_reflns_used    3497
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.025
_cell_measurement_theta_min      2.724
_cell_volume                     1646.6(6)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.686
_diffrn_measured_fraction_theta_max 0.687
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4767
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.62
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.1615 before and 0.1080 after correction.
        The Ratio of minimum to maximum transmission is 0.7680.
        The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         1999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0674
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1034P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.1809
_reflns_number_gt                1359
_reflns_number_total             1999
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4012212_si_004.cif
_cod_data_source_block           sci137_pr1176b2_0m
_cod_original_cell_volume        1646.7(6)
_cod_database_code               1556175