Ring Closure Reactions of 2,6-Diazaheptatrienyl Metal Compounds: Synthesis of 3-Aminoindole Derivatives and 14-Membered Macrocyclic Dimers
Benedikt Neue; Ralph Reiermann; Klaus Gerdes; Roland Fröhlich; Birgit Wibbeling; Ernst-Ulrich Würthwein; Journal of Organic Chemistry 76 (2011) 8794–8806; doi:10.1021/jo201521v

data_4026697
_publ_section_title
;
 Ring Closure Reactions of 2,6-Diazaheptatrienyl Metal Compounds:
 Synthesis of 3-Aminoindole Derivatives and 14-Membered Macrocyclic Dimers
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8794
_journal_page_last               8806
_journal_paper_doi               10.1021/jo201521v
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C44 H36 Br4 Cl4 N4'
_chemical_formula_weight         1082.21
_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   'at N from difmap, others geom'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.606(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.2030(3)
_cell_length_b                   14.5941(4)
_cell_length_c                   18.6700(7)
_cell_measurement_reflns_used    7603
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     4385.5(2)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwiniwski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38833
_diffrn_reflns_theta_full        67.30
_diffrn_reflns_theta_max         67.30
_diffrn_reflns_theta_min         4.09
_exptl_absorpt_coefficient_mu    7.008
_exptl_absorpt_correction_T_max  0.6397
_exptl_absorpt_correction_T_min  0.3346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_description       plate
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.110
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         7682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0383P)^2^+8.0498P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                6822
_reflns_number_total             7682
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201521v_si_012.cif
_cod_data_source_block           wue5754
_cod_database_code               4026697