Intramolecular Photoassisted Cycloadditions of Azaxylylenes and Postphotochemical Capstone Modifications via Suzuki Coupling Provide Access to Complex Polyheterocyclic Biaryls.
Cronk, W. Cole; Mukhina, Olga A.; Kutateladze, Andrei G.; The Journal of organic chemistry 79 (2014) 1235–; doi:10.1021/jo4026447

data_4029050
_publ_section_title
;
 Intramolecular Photoassisted Cycloadditions of Azaxylylenes and
 Postphotochemical Capstone Modifications via Suzuki Coupling Provide
 Access to Complex Polyheterocyclic Biaryls.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1235
_journal_paper_doi               10.1021/jo4026447
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C18 H15 N O4'
_chemical_formula_sum            'C18 H15 N O4'
_chemical_formula_weight         309.31
_chemical_name_systematic
;
5-(furan-2-yl)-2-hydroxy-16-oxa-9-azatetracyclo
[11.2.1.0^3,8^.0^5,9^]hexadeca-3,5,7,14-tetraen-10-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.117(5)
_cell_angle_beta                 90.020(5)
_cell_angle_gamma                92.618(5)
_cell_formula_units_Z            4
_cell_length_a                   7.6925(9)
_cell_length_b                   13.0724(16)
_cell_length_c                   14.1160(17)
_cell_measurement_reflns_used    9680
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.61
_cell_measurement_theta_min      2.65
_cell_volume                     1418.0(3)
_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      296(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 APEX II Diffractometer'
_diffrn_measurement_method       '\f and \w 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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0090
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            44737
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9969
_exptl_absorpt_correction_T_min  0.9857
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       square
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.859
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.859
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0748P)^2^+0.4882P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                4591
_reflns_number_total             5001
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4026447_si_002.cif
_cod_data_source_block           wcc33324_f39
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               4029050