Ethyl 5-(4-methylphenyl)-2,4,5,7-tetraazatricyclo[6.4.0.0^2,6^]dodeca-1(8),3,6,9,11-pentaene-3-carboxylate
Moussaif, Ahmed; Ramli, Youssef; El Ghayati, Lhoussaine; Essassi, El Mokhtar; Mague, Joel T.; IUCrData 3 (2018) x180892–; doi:10.1107/S2414314618008921

data_1549584
_publ_section_title
;
 Ethyl
 5-(4-methylphenyl)-2,4,5,7-tetraazatricyclo[6.4.0.0^2,6^]dodeca-1(8),3,6,9,11-pentaene-3-carboxylate
;
_journal_coeditor_code           HB4241
_journal_issue                   6
_journal_name_full               IUCrData
_journal_page_first              x180892
_journal_paper_doi               10.1107/S2414314618008921
_journal_volume                  3
_journal_year                    2018
_chemical_formula_iupac          'C18 H16 N4 O2'
_chemical_formula_moiety         'C18 H16 N4 O2'
_chemical_formula_sum            'C18 H16 N4 O2'
_chemical_formula_weight         320.35
_chemical_name_systematic
'Ethyl 5-(4-methylphenyl)-2,4,5,7-tetraazatricyclo[6.4.0.0^2,6^]dodeca-1(8),3,6,9,11-pentaene-3-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 92.144(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2366(11)
_cell_length_b                   10.2045(12)
_cell_length_c                   16.1922(18)
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.1671
_cell_measurement_theta_min      2.4992
_cell_volume                     1525.1(3)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_reduction
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
<i>SHELXTL</i> (Sheldrick, 2008)
;
_computing_structure_refinement
;
<i>SHELXL2018</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28729
_diffrn_reflns_theta_full        29.250
_diffrn_reflns_theta_max         29.264
_diffrn_reflns_theta_min         2.360
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0837P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1255
_reflns_number_gt                3269
_reflns_number_total             4119
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb4241sup1.cif
_cod_data_source_block           I
_cod_database_code               1549584
_cod_database_fobs_code          1549584
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.990
_shelx_hkl_checksum              21898
_shelx_res_checksum              18155