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_4028221
_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 Cl N2 O2'
_chemical_formula_sum            'C10 H7 Cl N2 O2'
_chemical_formula_weight         222.63
_chemical_melting_point          499
_chemical_name_common            'caulibugulone C'
_chemical_name_systematic        6-chloro-7-(methylamino)isoquinoline-5,8-dione
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.509(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.3738(4)
_cell_length_b                   5.4329(4)
_cell_length_c                   16.3535(12)
_cell_measurement_reflns_used    2458
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      36.22
_cell_measurement_theta_min      1.25
_cell_volume                     475.24(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2458
_diffrn_reflns_theta_full        36.22
_diffrn_reflns_theta_max         36.22
_diffrn_reflns_theta_min         1.25
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  0.9260
_exptl_absorpt_correction_T_min  0.4172
_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 0.946.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.851
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2458
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.851
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0387
_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^)+(0.1151P)^2^+0.0410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1442
_reflns_number_gt                1869
_reflns_number_total             2458
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302772t_si_004.cif
_cod_data_source_block           Caulibugulone_C
_cod_database_code               4028221