Expedient entry to the piperazinohydroisoquinoline ring system using a sequential Ugi/Pictet-Spengler/reductive methylation reaction protocol
Ma.-Angeles Cano-Herrera; Luis D. Miranda; Chem.Commun. 47 (2011) 10770–; doi:10.1039/c1cc10759c

data_7106862
_publ_section_title
;
 Expedient entry to the piperazinohydroisoquinoline ring system using a
 sequential Ugi/Pictet-Spengler/reductive methylation reaction protocol
;
_journal_name_full               Chem.Commun.
_journal_page_first              10770
_journal_paper_doi               10.1039/c1cc10759c
_journal_volume                  47
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C26 H32 N4 O6'
_chemical_formula_sum            'C26 H32 N4 O6'
_chemical_formula_weight         496.56
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   12.5407(19)
_cell_length_b                   13.946(2)
_cell_length_c                   15.358(2)
_cell_measurement_reflns_used    2550
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      17.88
_cell_measurement_theta_min      2.56
_cell_volume                     2686.0(7)
_computing_cell_refinement       'SMART V 5.625 (Bruker, 1999)'
_computing_data_collection       'SMART V 5.625 (Bruker, 1999)'
_computing_data_reduction        'SAINT V 6.23A (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 0.83
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker Smart APEX AXS CCD area detector 01-670'
_diffrn_measurement_method       '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  0.1358
_diffrn_reflns_av_sigmaI/netI    0.0934
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_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            30038
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_correction_T_min  0.9774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs,Sheldrick, G. M. (1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 2155 Friedel pairs were merged'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4950
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1723
_refine_ls_R_factor_gt           0.0812
_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^)+(0.0422P)^2^+1.1838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1599
_reflns_number_gt                2539
_reflns_number_total             4950
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10759c.txt
_cod_data_source_block           144mgl11
_cod_database_code               7106862
_solved_by                       'Simon Hernandez-Ortega'