Tetrahydro-β-carboline-Based Spirocyclic Lactam as Type II' β-Turn: Application to the Synthesis and Biological Evaluation of Somatostatine Mimetics
Giordano Lesma; Roberto Cecchi; Alfredo Cagnotto; Marco Gobbi; Fiorella Meneghetti; Manuele Musolino; Alessandro Sacchetti; Alessandra Silvani; Journal of Organic Chemistry 78 (2013) 2600–2610; doi:10.1021/jo302737j

data_4028054
_publ_contact_author_email       fiorella.meneghetti@unimi.it
_publ_contact_author_fax         '+39 2 50319359'
_publ_contact_author_name        'Meneghetti, Fiorella'
_publ_contact_author_phone       '+39 2 50319306'
_publ_section_title
;
 Tetrahydro-\b-carboline-Based Spirocyclic Lactam as Type II' \b-Turn:
 Application to the Synthesis and Biological Evaluation of Somatostatine
 Mimetics
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2600
_journal_page_last               2610
_journal_paper_doi               10.1021/jo302737j
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_sum            'C20 H24 N4 O3'
_chemical_formula_weight         368.43
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-11-09T11:52:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.670(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.491(4)
_cell_length_b                   7.053(5)
_cell_length_c                   15.167(8)
_cell_measurement_temperature    293(2)
_cell_volume                     895.4(9)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled \w/2\t scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.118874
_diffrn_orient_matrix_UB_12      0.013958
_diffrn_orient_matrix_UB_13      0.011264
_diffrn_orient_matrix_UB_21      -0.011579
_diffrn_orient_matrix_UB_22      0.13837
_diffrn_orient_matrix_UB_23      -0.014031
_diffrn_orient_matrix_UB_31      -0.002479
_diffrn_orient_matrix_UB_32      0.027621
_diffrn_orient_matrix_UB_33      0.064416
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2216
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.43
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        -39
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       prisms
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.029(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         2216
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1369P)^2^+0.0650P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1592
_reflns_number_gt                1998
_reflns_number_total             2216
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302737j_si_002.cif
_cod_data_source_block           ascr06
_cod_database_code               4028054