Synthesis of Functionalized Pseudopeptides through Five-Component Sequential Ugi/Nucleophilic Reaction of N-Substituted 2-Alkynamides with Hydrazides
Shokoofeh Maghari; Sorour Ramezanpour; Saeed Balalaie; Fatemeh Darvish; Frank Rominger; Hamid Reza Bijanzadeh; Journal of Organic Chemistry 78 (2013) 6450–6456; doi:10.1021/jo4003294

data_4028383
_publ_contact_author_address
;      Peptide Chemistry Research Center
       K. N. Toosi University of Technology
       P. O. Box: 15875-4416 
       Tehran
       Iran
;
_publ_contact_author_email       balalaie@kntu.ac.ir
_publ_contact_author_fax         '+98 21 22853650'
_publ_contact_author_name        'Balalaie, Saeed'
_publ_contact_author_phone       '+98 21 22850266'
_publ_section_title
;
 Synthesis of Functionalized Pseudopeptides through Five-Component
 Sequential Ugi/Nucleophilic Reaction of N-Substituted 2-Alkynamides with
 Hydrazides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6450
_journal_page_last               6456
_journal_paper_doi               10.1021/jo4003294
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C30 H32 N4 O3'
_chemical_formula_weight         496.60
_space_group_IT_number           41
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'A 2 -2ab'
_symmetry_space_group_name_H-M   'A b a 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.2631(12)
_cell_length_b                   35.327(3)
_cell_length_c                   8.9843(6)
_cell_measurement_reflns_used    9521
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.43
_cell_measurement_theta_min      2.31
_cell_volume                     5479.1(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II Quazar'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  mirror'
_diffrn_radiation_source         'ImuS microsource'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            28519
_diffrn_reflns_theta_full        26.52
_diffrn_reflns_theta_max         26.52
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_correction_T_min  0.9813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). <i>SADABS</i>. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       needle
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         3028
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0442P)^2^+3.1883P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1000
_reflns_number_gt                2670
_reflns_number_total             3028
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4003294_si_001.cif
_cod_data_source_block           sba91
_cod_database_code               4028383