Crystal structure and Hirshfeld surface analysis of two 5,11-methanobenzo[<i>g</i>][1,2,4]triazolo[1,5-<i>c</i>][1,3,5]oxadiazocine derivatives
Gumus, Mustafa Kemal; Kansiz, Sevgi; Yuksektepe Ataol, Cigdem; Dege, Necmi; Fritsky, Igor O.; Acta Crystallographica Section E 75 (2019) 492–498; doi:10.1107/S2056989019003700

data_2242876
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of two
 5,11-methanobenzo[<i>g</i>][1,2,4]triazolo[1,5-<i>c</i>][1,3,5]oxadiazocine
 derivatives
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              492
_journal_page_last               498
_journal_paper_doi               10.1107/S2056989019003700
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C13 H13 Br N4 O'
_chemical_formula_moiety         'C13 H13 Br N4 O'
_chemical_formula_sum            'C13 H13 Br N4 O'
_chemical_formula_weight         321.18
_chemical_name_systematic
9-Bromo-2,5-dimethyl-11,12-dihydro-5<i>H</i>-5,11-methanobenzo[<i>g</i>][1,2,4]triazolo[1,5-<i>c</i>][1,3,5]oxadiazocine
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                109.657(7)
_cell_angle_beta                 92.325(8)
_cell_angle_gamma                91.664(7)
_cell_formula_units_Z            2
_cell_length_a                   6.1446(6)
_cell_length_b                   9.7407(8)
_cell_length_c                   11.6801(11)
_cell_measurement_reflns_used    9169
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.52
_cell_measurement_theta_min      2.36
_cell_volume                     657.13(11)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2002)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2008) and PLATON (Spek, 2009)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), SHELXL2018 (Sheldrick, 2015b),
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2017 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.209
_diffrn_reflns_theta_min         2.365
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    3.125
_exptl_absorpt_correction_T_max  0.7478
_exptl_absorpt_correction_T_min  0.4765
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe & Cie, 2002)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_description       prism
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.703
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         4242
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0513P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                2223
_reflns_number_total             4242
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            su5490sup1.cif
_cod_data_source_block           I
_cod_database_code               2242876
_cod_database_fobs_code          2242876
_shelx_hkl_checksum              68135
_shelx_res_checksum              87621