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_4028149
_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                 90.782(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.8582(16)
_cell_length_b                   8.4797(15)
_cell_length_c                   32.907(6)
_cell_measurement_reflns_used    1440
_cell_measurement_temperature    180.0(5)
_cell_measurement_theta_max      24.78
_cell_measurement_theta_min      2.30
_cell_volume                     2471.6(8)
_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      180.0(5)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.978
_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  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0633
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6796
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.41
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0015(4)
_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   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.3433P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                2607
_reflns_number_total             4463
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo400179u_si_002_09.cif
_cod_data_source_block           6Ef
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4028149