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_7152484
_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_formula_sum            'C11 H9 N3 O2'
_chemical_formula_weight         215.21
_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                   4.9819(5)
_cell_length_b                   6.5576(6)
_cell_length_c                   28.039(3)
_cell_measurement_reflns_used    1331
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      58.106
_cell_measurement_theta_min      3.152
_cell_volume                     916.01(16)
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            4855
_diffrn_reflns_theta_full        58.83
_diffrn_reflns_theta_max         58.83
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.8890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0040(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0623P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0933
_reflns_number_gt                702
_reflns_number_total             823
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25353d.txt
_cod_data_source_block           liming4b_0m
_cod_original_cell_volume        916.01(15)
_cod_database_code               7152484