Practical synthesis and cytotoxic evaluation of the pyrazino[1,2-b]-isoquinoline ring system.
Hernández-Vázquez, Eduardo; Miranda, Luis D.; Organic & biomolecular chemistry 14 (2016) 4875–4884; doi:10.1039/c6ob00431h

data_7155100
_publ_section_title
;
 Practical synthesis and cytotoxic evaluation of the
 pyrazino[1,2-b]-isoquinoline ring system.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4875
_journal_page_last               4884
_journal_paper_doi               10.1039/c6ob00431h
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C21 H20 N2 O2'
_chemical_formula_sum            'C21 H20 N2 O2'
_chemical_formula_weight         332.39
_chemical_melting_point          134.5(15)
_chemical_name_systematic
'2-(2,6-dimethylphenyl)-9-methyl-2H-pyrazino[1,2-b]isoquinoline-1,4(3H,6H)-dione '
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-02-26 deposited with the CCDC.
2016-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.803(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7074(4)
_cell_length_b                   16.5340(5)
_cell_length_c                   7.8722(2)
_cell_measurement_reflns_used    4326
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.27
_cell_measurement_theta_min      2.46
_cell_volume                     1732.62(9)
_computing_cell_refinement       'APEX2 V2012 (Bruker, 2012)'
_computing_data_collection       'APEX2 V2012 (Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B  (Bruker, 2012)'
_computing_molecular_graphics    'SHELXTL  (Sheldrick, 2013)'
_computing_publication_material  'SHELXTL  (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXTL  (Sheldrick, 2013)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 0.83
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1534
_diffrn_reflns_av_unetI/netI     0.1121
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12483
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.306
_diffrn_reflns_theta_min         1.964
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       Prism
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2/Hexane'
_exptl_crystal_size_max          0.439
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0103(17)
_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   0.912
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.912
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.0523P)^2^] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1404
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1611
_reflns_number_total             3139
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00431h2.cif
_cod_data_source_block           518mgl14
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '133-136' was changed to '134.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155100--7155101.cif.
;
_cod_database_code               7155100
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.994
_shelxl_version_number           2013-2
_shelx_res_checksum              65502