Synthesis of 1,2,4-triazines and the triazinoisoquinolinedione DEF ring system of noelaquinone.
Cao, Liming; Maciejewski, John P.; Elzner, Stephan; Amantini, David; Wipf, Peter; Organic & biomolecular chemistry 10 (2012) 5811–5814; doi:10.1039/c2ob25353d

data_7152482
_publ_section_title
;
 Synthesis of 1,2,4-triazines and the triazinoisoquinolinedione DEF ring
 system of noelaquinone.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5811
_journal_page_last               5814
_journal_paper_doi               10.1039/c2ob25353d
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_sum            'C18 H15 N3 O2'
_chemical_formula_weight         305.33
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9211(3)
_cell_length_b                   12.5759(8)
_cell_length_c                   23.0138(15)
_cell_measurement_temperature    100(2)
_cell_volume                     1424.26(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.965
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6323
_diffrn_reflns_theta_full        61.00
_diffrn_reflns_theta_max         61.24
_diffrn_reflns_theta_min         4.01
_exptl_absorpt_coefficient_mu    0.774
_exptl_absorpt_correction_T_max  0.9697
_exptl_absorpt_correction_T_min  0.9266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.784
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         1280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.784
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0784
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1707
_refine_ls_wR_factor_ref         0.1722
_reflns_number_gt                1186
_reflns_number_total             1280
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25353d.txt
_cod_data_source_block           liming1
_cod_database_code               7152482