Exploitation of a Tuned Oxidation with N-Haloimides in the Synthesis of Caulibugulones A-D
Fabrício F. Naciuk; Julio C. Milan; Almir Andreão; Paulo C. M. L. Miranda; Journal of Organic Chemistry 78 (2013) 5026–5030; doi:10.1021/jo302772t

data_4028220
_publ_contact_author_address     'UNICAMP - Brazil'
_publ_contact_author_email       miranda@iqm.unicamp.br
_publ_contact_author_name        'Julio Milan'
_publ_contact_author_phone       +55.19.35.21.30.83
_publ_section_title
;
 Exploitation of a Tuned Oxidation with N-Haloimides in the Synthesis of
 Caulibugulones A-D
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5026
_journal_page_last               5030
_journal_paper_doi               10.1021/jo302772t
_journal_volume                  78
_journal_year                    2013
_chemical_compound_source        'total synthesis'
_chemical_formula_moiety         'C10 H7 Br N2 O2'
_chemical_formula_sum            'C10 H7 Br N2 O2'
_chemical_formula_weight         267.08
_chemical_melting_point          499
_chemical_name_common            'caulibugulone B'
_chemical_name_systematic        6-bromo-7-(methylamino)isoquinoline-5,8-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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_date             2012-10-22
_audit_creation_method
;
  Olex2 1.2
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.997(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8820(8)
_cell_length_b                   7.6896(6)
_cell_length_c                   11.7402(9)
_cell_measurement_reflns_used    4723
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.75
_cell_measurement_theta_min      2.26
_cell_volume                     944.36(12)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16283
_diffrn_reflns_theta_full        30.64
_diffrn_reflns_theta_max         30.64
_diffrn_reflns_theta_min         2.26
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.331
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0599 before and 0.0341 after correction.
The Ratio of minimum to maximum transmission is 0.7709.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.886
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.292
_exptl_crystal_size_mid          0.262
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.3916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0756
_reflns_number_gt                2112
_reflns_number_total             2898
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302772t_si_003.cif
_cod_data_source_block           Caulibugulone_B
_cod_database_code               4028220