Crystal structure of 5-benzyl-8-bromo-2-methyl-1,3-oxazolo[4,5-<i>c</i>][1,8]naphthyridin-4(5<i>H</i>)-one
Vrijdag, Johannes; Van den Bogaert, An; De Borggraeve, Wim; Van Meervelt, Luc; Acta Crystallographica Section E 73 (2017) 687–690; doi:10.1107/S2056989017005023

data_2242133
_publ_section_title
;
 Crystal structure of
 5-benzyl-8-bromo-2-methyl-1,3-oxazolo[4,5-<i>c</i>][1,8]naphthyridin-4(5<i>H</i>)-one
;
_journal_coeditor_code           RZ5210
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              687
_journal_page_last               690
_journal_paper_doi               10.1107/S2056989017005023
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C17 H12 Br N3 O2'
_chemical_formula_moiety         'C17 H12 Br N3 O2'
_chemical_formula_sum            'C17 H12 Br N3 O2'
_chemical_formula_weight         370.21
_chemical_name_systematic
5-Benzyl-8-bromo-2-methyl[1,3]oxazolo[4,5-<i>c</i>]-1,8-naphthyridin-4(5<i>H</i>)-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7150(13)
_cell_length_b                   13.504(3)
_cell_length_c                   16.757(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      1.94
_cell_volume                     1519.5(5)
_computing_cell_refinement
;
CAD-4 Express (Enraf--Nonius, 1989)
;
_computing_data_collection
;
CAD-4 Express (Enraf--Nonius, 1989)
;
_computing_data_reduction
;
<i>DREAR</i> (Blessing, 1987)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
<i>SHELXL2014/7</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       '\w/2\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1429
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.302
_diffrn_reflns_theta_min         1.937
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.718
_exptl_absorpt_correction_T_max  0.5775
_exptl_absorpt_correction_T_min  0.5218
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
(North <i>et al.</i>,  1968)
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.272
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.000(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1429
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0221P)^2^+0.5935P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0687
_reflns_number_gt                1279
_reflns_number_total             1429
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           I
_cod_database_code               2242133
_cod_database_fobs_code          2242133