Extending Pummerer Reaction Chemistry: Studies in the Palau'amine Synthesis Area
Ken S. Feldman; Ahmed Yimam Nuriye; Jianfeng Li; Journal of Organic Chemistry 76 (2011) 5042–5060; doi:10.1021/jo200740b

data_4026398
_publ_section_title
;
 Extending Pummerer Reaction Chemistry: Studies in the Palau'amine
 Synthesis Area
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5042
_journal_page_last               5060
_journal_paper_doi               10.1021/jo200740b
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C26 H34 Br2 N4 O2 S Si'
_chemical_formula_sum            'C26 H34 Br2 N4 O2 S Si'
_chemical_formula_weight         654.55
_chemical_melting_point          158(1)
_chemical_name_systematic
; 
 4,5-Dibromo-1H-pyrrole-2-carboxylic acid 
{2-[2-phenylsulfanyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-yl]
-cyclopentylmethyl}-amide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.905(4)
_cell_angle_beta                 98.513(4)
_cell_angle_gamma                103.071(4)
_cell_formula_units_Z            2
_cell_length_a                   8.838(2)
_cell_length_b                   12.387(3)
_cell_length_c                   13.856(4)
_cell_measurement_reflns_used    8770
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.299
_cell_measurement_theta_min      2.383
_cell_volume                     1453.2(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13922
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    2.932
_exptl_absorpt_correction_T_max  0.473
_exptl_absorpt_correction_T_min  0.435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       cubic
_exptl_crystal_F_000             669
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         1.034
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         7030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0652P)^2^+1.0024P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                6090
_reflns_number_total             7030
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200740b_si_002.cif
_cod_data_source_block           jxl2s
_cod_database_code               4026398