A Highly Convergent Synthesis of Tricyclic N-Heterocycles Coupling an Ugi Reaction with a Tandem SN2'-Heck Double Cyclization
Renata Riva; Luca Banfi; Andrea Basso; Valentina Cerulli; Giuseppe Guanti; Marcella Pani; Journal of Organic Chemistry 75 (2010) 5134–5143; doi:10.1021/jo100859y

data_4025554
_publ_contact_author             'Renata Riva'
_publ_contact_author_email       riva@chimica.unige.it
_publ_section_title
;
 A Highly Convergent Synthesis of Tricyclic N-Heterocycles Coupling an Ugi
 Reaction with a Tandem SN2'-Heck Double Cyclization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5134
_journal_page_last               5143
_journal_paper_doi               10.1021/jo100859y
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C24 H26 N2 O2'
_chemical_formula_sum            'C24 H26 N2 O2'
_chemical_formula_weight         374.47
_chemical_name_systematic
;
6-(N-benzyl-Npropanoyl)amino-13-methylene-5-oxo
-2,3,5,6,12,13-hexahydro-1H-benzo[d]pyrrolo[1,2-a]azepine
;
_chemical_temperature_decomposition_gt 433.1
_chemical_temperature_decomposition_lt 435.9
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 93.38(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.641(1)
_cell_length_b                   16.342(3)
_cell_length_c                   12.793(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      17.31
_cell_measurement_theta_min      15.13
_cell_volume                     2012.1(5)
_computing_cell_refinement       'MACH3 software'
_computing_data_collection       'MACH3 software'
_computing_data_reduction        'local software'
_computing_molecular_graphics    'ORTEP-III for windows'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'sir2004 (J. Appl. Cryst. 38, 2005, 381-388)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0803
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5015
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  180
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_correction_T_min  0.8741
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular prism'
_exptl_crystal_F_000             800
_exptl_crystal_preparation
'crystallized from dichloromethane/isopropylether'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0096(11)
_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   0.914
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4813
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.1685
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0548P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1341
_reflns_number_gt                2072
_reflns_number_total             4813
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100859y_si_003.cif
_cod_data_source_block           trans-4a
_cod_depositor_comments
;
The following automatic conversions were performed:
data name '_publ_contact_email' replaced with
'_publ_contact_author_email' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 4998 2017-03-02 13:24:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4025554