Stereospecific Suzuki, Sonogashira, and Negishi Coupling Reactions of N-Alkoxyimidoyl Iodides and Bromides
Debra D. Dolliver; Bijay T. Bhattarai; Arjun Pandey; Megan L. Lanier; Amber S. Bordelon; Sarju Adhikari; Jordan A. Dinser; Patrick F. Flowers; Veronica S. Wills; Caroline L. Schneider; Kevin H. Shaughnessy; Jane N. Moore; Steven M. Raders; Timothy S. Snowden; Artie S. McKim; Frank R. Fronczek; Journal of Organic Chemistry 78 (2013) 3676–3687; doi:10.1021/jo400179u

data_4028144
_publ_section_title
;
 Stereospecific Suzuki, Sonogashira, and Negishi Coupling Reactions of
 N-Alkoxyimidoyl Iodides and Bromides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3676
_journal_page_last               3687
_journal_paper_doi               10.1021/jo400179u
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C14 H12 N2 O3'
_chemical_formula_sum            'C14 H12 N2 O3'
_chemical_formula_weight         256.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 108.144(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0615(15)
_cell_length_b                   8.4714(10)
_cell_length_c                   13.820(2)
_cell_measurement_reflns_used    9806
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      41.15
_cell_measurement_theta_min      2.83
_cell_volume                     1230.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            40327
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         41.16
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9766
_exptl_absorpt_correction_T_min  0.9642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         8184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0648P)^2^+0.1901P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1200
_reflns_number_gt                6893
_reflns_number_total             8184
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo400179u_si_002_04.cif
_cod_data_source_block           6Ee
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4028144