Crystal structure of 12-benzylsulfanyl-2,9-dibromo-6<i>H</i>-dibenzo[<i>b</i>,<i>g</i>][1,8]naphthyridin-11-one
Resch, Sebastian; Quell, Thomas; Schollmeyer, Dieter; Waldvogel, Siegfried R.; Acta Crystallographica Section E 71 (2015) o675–o676; doi:10.1107/S2056989015014541

data_2241023
_publ_section_title
;
 Crystal structure of
 12-benzylsulfanyl-2,9-dibromo-6<i>H</i>-dibenzo[<i>b</i>,<i>g</i>][1,8]naphthyridin-11-one
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o675
_journal_page_last               o676
_journal_paper_doi               10.1107/S2056989015014541
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C23 H14 Br2 N2 O S'
_chemical_formula_moiety         'C23 H14 Br2 N2 O S'
_chemical_formula_sum            'C23 H14 Br2 N2 O S'
_chemical_formula_weight         526.24
_chemical_name_common
;
12-Benzylsulfanyl-2,9-dibromo-6<i>H</i>-dibenzo[<i>b</i>,<i>g</i>]\
[1,8]naphthyridin-11-one
;
_chemical_name_systematic
;
12-Benzylsulfanyl-2,9-dibromo-6,11-dihydro-5-azatetracen-11-one
;
_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-2014
_cell_angle_alpha                90
_cell_angle_beta                 101.251(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4915(10)
_cell_length_b                   9.3953(4)
_cell_length_c                   13.6501(9)
_cell_measurement_reflns_used    7178
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.55
_cell_volume                     1948.6(2)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 1995)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 1995)
;
_computing_data_reduction
;
X-RED (Stoe & Cie, 1995)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2004 (Burla <i>et al.</i>,  2005)
;
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10437
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.313
_diffrn_reflns_theta_min         2.549
_exptl_absorpt_coefficient_mu    4.286
_exptl_absorpt_correction_T_max  0.8108
_exptl_absorpt_correction_T_min  0.3629
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
X-RED (Stoe & Cie, 1995)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.294
_refine_diff_density_min         -1.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1106P)^2^+4.6375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1663
_refine_ls_wR_factor_ref         0.2220
_reflns_number_gt                2850
_reflns_number_total             4807
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            wm5191sup1.cif
_cod_data_source_block           I
_cod_database_code               2241023
_cod_database_fobs_code          2241023
_shelx_estimated_absorpt_t_min   0.391
_shelx_estimated_absorpt_t_max   0.847
_shelx_hkl_checksum              61429
_shelx_res_checksum              70145
_shelxl_version_number           2.014