Palladium-Catalyzed Multicomponent Synthesis of 2-Aryl-2-imidazolines from Aryl Halides and Diamines
Joanna V. Geden; Alpa K. Pancholi; Michael Shipman; Journal of Organic Chemistry 78 (2013) 4158–4164; doi:10.1021/jo400252n

data_4028159
_publ_section_title
;
 Palladium-Catalyzed Multicomponent Synthesis of 2-Aryl-2-imidazolines
 from Aryl Halides and Diamines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4158
_journal_page_last               4164
_journal_paper_doi               10.1021/jo400252n
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C11 H13 N5'
_chemical_formula_sum            'C11 H13 N5'
_chemical_formula_weight         215.26
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                90.00
_cell_angle_beta                 96.532(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5759(3)
_cell_length_b                   6.6953(3)
_cell_length_c                   19.3769(10)
_cell_measurement_reflns_used    1908
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.29
_cell_measurement_theta_min      3.01
_cell_volume                     976.47(8)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) x-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            4298
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         30.46
_diffrn_reflns_theta_min         4.07
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSPACK(CrysAlis, Oxford Diffraction)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         1336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0640
_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^)+(0.0983P)^2^+0.2169P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1701
_reflns_number_gt                1097
_reflns_number_total             1336
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400252n_si_002.cif
_cod_data_source_block           jg1
_cod_database_code               4028159