Concise construction of novel bridged bicyclic lactams by sequenced Ugi/RCM/Heck reactions.
Ribelin, Timothy P.; Judd, Andrew S.; Akritopoulou-Zanze, Irini; Henry, Rodger F.; Cross, Jeffrey L.; Whittern, David N.; Djuric, Stevan W.; Organic letters 9 (2007) 5119–5122; doi:10.1021/ol7023373

data_1505631
_publ_section_title
;
 Concise construction of novel bridged bicyclic lactams by sequenced
 Ugi/RCM/Heck reactions.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5119
_journal_page_last               5122
_journal_paper_doi               10.1021/ol7023373
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C18 H19 N3 O2'
_chemical_formula_weight         309.36
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.469(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.023(3)
_cell_length_b                   13.658(3)
_cell_length_c                   17.593(5)
_cell_measurement_reflns_used    1023
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.1145
_cell_measurement_theta_min      2.3855
_cell_volume                     3090.8(13)
_computing_cell_refinement       'Bruker saintplus (Bruker 1999)'
_computing_data_collection       'Bruker SMART (Bruker 2001)'
_computing_data_reduction        'Bruker saintplus (Bruker 1999)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2000)'
_computing_structure_solution    'SHELXL (Sheldrick, 2000)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'APEX CCD'
_diffrn_measurement_method       omega
_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  0.2298
_diffrn_reflns_av_sigmaI/netI    0.1127
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35382
_diffrn_reflns_theta_full        28.18
_diffrn_reflns_theta_max         28.18
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       'not refined'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         7486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          4.177
_refine_ls_shift/su_mean         0.220
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0957P)^2^+0.6220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1920
_refine_ls_wR_factor_ref         0.1995
_reflns_number_gt                6428
_reflns_number_total             7486
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ol7023373-file003.cif
_cod_data_source_block           compound6d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        3090.7(13)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1505631