#------------------------------------------------------------------------------ #$Date: 2020-05-01 05:44:41 +0300 (Fri, 01 May 2020) $ #$Revision: 251360 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/79/1557980.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_1557980 loop_ _publ_author_name 'Crundwell, Guy' 'Leeds, Ashley' _publ_section_title ; 2,3-Diethylbenzo[g]quinoxaline ; _journal_coeditor_code HB4346 _journal_issue 4 _journal_name_full IUCrData _journal_page_first x200454 _journal_paper_doi 10.1107/S241431462000454X _journal_volume 5 _journal_year 2020 _chemical_absolute_configuration unk _chemical_formula_iupac 'C16 H16 N2' _chemical_formula_moiety 'C16 H16 N2' _chemical_formula_sum 'C16 H16 N2' _chemical_formula_weight 236.31 _chemical_melting_point 411 _chemical_name_common 2,3-Diethylbenzo[g]quinoxaline _chemical_name_systematic ; 2,3-Diethylbenzo[g]quinoxaline ; _space_group_crystal_system tetragonal _space_group_IT_number 82 _space_group_name_Hall 'I -4' _space_group_name_H-M_alt 'I -4' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 13.93535(18) _cell_length_b 13.93535(18) _cell_length_c 13.1629(3) _cell_measurement_reflns_used 7488 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 31.7740 _cell_measurement_theta_min 4.6020 _cell_volume 2556.16(7) _computing_cell_refinement ; CrysAlisPro (Rigaku, 2018) ; _computing_data_collection ; CrysAlisPro (Rigaku, 2018) ; _computing_data_reduction ; CrysAlisPro (Rigaku, 2018) ; _computing_molecular_graphics ; OLEX2 (Dolomanov et al., 2009) ; _computing_publication_material ; OLEX2 (Dolomanov et al., 2009) ; _computing_structure_refinement ; SHELXL (Sheldrick, 2008) ; _computing_structure_solution ; SHELXM (Sheldrick, 2008) ; _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.1790 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.965 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Rigaku Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_unetI/netI 0.0198 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 31103 _diffrn_reflns_theta_full 29.00 _diffrn_reflns_theta_max 33.55 _diffrn_reflns_theta_min 4.26 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlisPro; Rigaku, 2018) ; _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1008 _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.27 _refine_diff_density_max 0.284 _refine_diff_density_min -0.143 _refine_ls_abs_structure_details ; Flack H D (1983), Acta Cryst. A39, 876-881 ; _refine_ls_abs_structure_Flack 0(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 165 _refine_ls_number_reflns 4779 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0477 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0756P)^2^+0.2732P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1256 _refine_ls_wR_factor_ref 0.1360 _reflns_number_gt 3869 _reflns_number_total 4779 _reflns_threshold_expression I>2\s(I) _cod_data_source_file hb4346sup1.cif _cod_data_source_block I _cod_database_code 1557980 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 'y, -x, -z' 3 '-x, -y, z' 4 '-y, x, -z' 5 'x+1/2, y+1/2, z+1/2' 6 'y+1/2, -x+1/2, -z+1/2' 7 '-x+1/2, -y+1/2, z+1/2' 8 '-y+1/2, x+1/2, -z+1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 -0.29561(13) -1.16936(12) -0.44274(13) 0.0600(4) Uani d 1 . . H H1A -0.3206 -1.1110 -0.4711 0.090 Uiso calc 1 . . H H1B -0.3333 -1.2227 -0.4659 0.090 Uiso calc 1 . . H H1C -0.2302 -1.1776 -0.4640 0.090 Uiso calc 1 . . C C2 -0.29974(10) -1.16422(10) -0.32887(12) 0.0493(3) Uani d 1 . . H H2A -0.2793 -1.2256 -0.3016 0.059 Uiso calc 1 . . H H2B -0.3660 -1.1546 -0.3087 0.059 Uiso calc 1 . . C C3 -0.23964(8) -1.08656(8) -0.28133(10) 0.0379(2) Uani d 1 . . C C4 -0.13277(8) -0.96118(8) -0.29463(9) 0.0328(2) Uani d 1 . . C C5 -0.07941(9) -0.89899(9) -0.35476(9) 0.0378(2) Uani d 1 . . H H5 -0.0815 -0.9047 -0.4251 0.045 Uiso calc 1 . . C C6 -0.02254(8) -0.82781(8) -0.31001(9) 0.0360(2) Uani d 1 . . C C7 0.03189(10) -0.76181(10) -0.36928(12) 0.0475(3) Uani d 1 . . H H7 0.0310 -0.7661 -0.4398 0.057 Uiso calc 1 . . C C8 0.08527(12) -0.69247(11) -0.32317(15) 0.0567(4) Uani d 1 . . H H8 0.1199 -0.6493 -0.3627 0.068 Uiso calc 1 . . C C9 0.08872(12) -0.68520(11) -0.21668(15) 0.0608(4) Uani d 1 . . H H9 0.1253 -0.6372 -0.1867 0.073 Uiso calc 1 . . C C10 0.03930(10) -0.74736(11) -0.15731(12) 0.0515(3) Uani d 1 . . H H10 0.0430 -0.7421 -0.0870 0.062 Uiso calc 1 . . C C11 -0.01854(8) -0.82097(9) -0.20173(10) 0.0369(2) Uani d 1 . . C C12 -0.07119(8) -0.88458(9) -0.14191(9) 0.0380(2) Uani d 1 . . H H12 -0.0676 -0.8806 -0.0715 0.046 Uiso calc 1 . . C C13 -0.12889(8) -0.95376(8) -0.18678(8) 0.0333(2) Uani d 1 . . C C14 -0.23818(8) -1.07610(9) -0.17124(10) 0.0381(2) Uani d 1 . . C C15 -0.30438(11) -1.13340(11) -0.10459(12) 0.0522(3) Uani d 1 . . H H15A -0.2763 -1.1398 -0.0375 0.063 Uiso calc 1 . . H H15B -0.3123 -1.1972 -0.1328 0.063 Uiso calc 1 . . C C16 -0.40207(12) -1.08493(14) -0.09594(16) 0.0684(5) Uani d 1 . . H H16A -0.4299 -1.0786 -0.1623 0.103 Uiso calc 1 . . H H16B -0.3945 -1.0225 -0.0661 0.103 Uiso calc 1 . . H H16C -0.4434 -1.1231 -0.0539 0.103 Uiso calc 1 . . N N1 -0.18907(7) -1.03067(7) -0.34033(9) 0.0388(2) Uani d 1 . . N N2 -0.18387(7) -1.01278(8) -0.12633(8) 0.0388(2) Uani d 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0616(8) 0.0543(8) 0.0641(10) -0.0115(7) -0.0117(8) -0.0176(7) C2 0.0434(6) 0.0432(7) 0.0613(9) -0.0115(5) -0.0068(6) -0.0058(6) C3 0.0336(5) 0.0337(5) 0.0463(6) -0.0024(4) -0.0068(5) -0.0029(4) C4 0.0293(5) 0.0313(5) 0.0377(5) -0.0020(4) -0.0033(4) -0.0039(4) C5 0.0381(5) 0.0396(6) 0.0358(5) -0.0027(4) -0.0006(4) -0.0041(4) C6 0.0306(5) 0.0336(5) 0.0439(6) -0.0011(4) 0.0009(4) -0.0024(4) C7 0.0441(6) 0.0445(6) 0.0539(8) -0.0059(5) 0.0057(6) 0.0018(6) C8 0.0494(8) 0.0470(7) 0.0738(11) -0.0151(6) 0.0073(7) 0.0010(7) C9 0.0510(8) 0.0494(8) 0.0820(12) -0.0184(6) -0.0056(8) -0.0122(8) C10 0.0467(7) 0.0515(7) 0.0563(8) -0.0122(6) -0.0081(6) -0.0113(6) C11 0.0302(5) 0.0360(5) 0.0446(6) 0.0000(4) -0.0049(4) -0.0058(4) C12 0.0365(6) 0.0423(6) 0.0353(5) -0.0022(4) -0.0059(4) -0.0042(4) C13 0.0292(5) 0.0340(5) 0.0368(5) 0.0016(4) -0.0041(4) 0.0006(4) C14 0.0341(5) 0.0356(5) 0.0445(6) 0.0005(4) -0.0041(5) 0.0067(5) C15 0.0550(8) 0.0455(7) 0.0561(8) -0.0093(6) -0.0022(6) 0.0152(6) C16 0.0504(8) 0.0754(11) 0.0794(11) -0.0118(8) 0.0130(8) 0.0169(9) N1 0.0364(5) 0.0390(5) 0.0409(5) -0.0054(4) -0.0047(4) -0.0056(4) N2 0.0384(5) 0.0402(5) 0.0378(5) -0.0016(4) -0.0044(4) 0.0044(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag H1A C1 H1B . . 109.5 no H1A C1 H1C . . 109.5 no H1B C1 H1C . . 109.5 no C2 C1 H1A . . 109.5 no C2 C1 H1B . . 109.5 no C2 C1 H1C . . 109.5 no C1 C2 H2A . . 108.4 no C1 C2 H2B . . 108.4 no C1 C2 C3 . . 115.34(12) no H2A C2 H2B . . 107.5 no C3 C2 H2A . . 108.4 no C3 C2 H2B . . 108.4 no C14 C3 C2 . . 119.57(11) no N1 C3 C2 . . 118.81(11) no N1 C3 C14 . . 121.62(10) no C5 C4 C13 . . 120.14(10) no N1 C4 C5 . . 119.49(10) no N1 C4 C13 . . 120.37(10) no C4 C5 H5 . . 119.8 no C4 C5 C6 . . 120.35(10) no C6 C5 H5 . . 119.8 no C5 C6 C7 . . 121.91(11) no C5 C6 C11 . . 119.27(11) no C7 C6 C11 . . 118.82(11) no C6 C7 H7 . . 119.8 no C8 C7 C6 . . 120.31(13) no C8 C7 H7 . . 119.8 no C7 C8 H8 . . 119.5 no C7 C8 C9 . . 120.93(14) no C9 C8 H8 . . 119.5 no C8 C9 H9 . . 119.6 no C10 C9 C8 . . 120.77(14) no C10 C9 H9 . . 119.6 no C9 C10 H10 . . 119.7 no C9 C10 C11 . . 120.63(14) no C11 C10 H10 . . 119.7 no C6 C11 C10 . . 118.53(12) no C12 C11 C6 . . 120.01(10) no C12 C11 C10 . . 121.46(12) no C11 C12 H12 . . 119.8 no C13 C12 C11 . . 120.42(10) no C13 C12 H12 . . 119.8 no C12 C13 C4 . . 119.79(10) no N2 C13 C4 . . 120.75(10) no N2 C13 C12 . . 119.44(10) no C3 C14 C15 . . 121.27(11) no N2 C14 C3 . . 121.79(11) no N2 C14 C15 . . 116.81(12) no C14 C15 H15A . . 109.5 no C14 C15 H15B . . 109.5 no C14 C15 C16 . . 110.89(12) no H15A C15 H15B . . 108.1 no C16 C15 H15A . . 109.5 no C16 C15 H15B . . 109.5 no C15 C16 H16A . . 109.5 no C15 C16 H16B . . 109.5 no C15 C16 H16C . . 109.5 no H16A C16 H16B . . 109.5 no H16A C16 H16C . . 109.5 no H16B C16 H16C . . 109.5 no C3 N1 C4 . . 117.69(10) no C14 N2 C13 . . 117.71(10) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 H1A . 0.9600 no C1 H1B . 0.9600 no C1 H1C . 0.9600 no C1 C2 . 1.502(2) n C2 H2A . 0.9700 no C2 H2B . 0.9700 no C2 C3 . 1.5047(17) no C3 C14 . 1.4566(18) no C3 N1 . 1.3062(16) no C4 C5 . 1.3894(15) no C4 C13 . 1.4245(15) no C4 N1 . 1.3839(13) no C5 H5 . 0.9300 no C5 C6 . 1.3997(16) no C6 C7 . 1.4247(17) no C6 C11 . 1.4296(17) no C7 H7 . 0.9300 no C7 C8 . 1.362(2) no C8 H8 . 0.9300 no C8 C9 . 1.406(3) no C9 H9 . 0.9300 no C9 C10 . 1.355(2) no C10 H10 . 0.9300 no C10 C11 . 1.4296(16) no C11 C12 . 1.3943(17) no C12 H12 . 0.9300 no C12 C13 . 1.3873(15) no C13 N2 . 1.3772(15) no C14 C15 . 1.5027(18) no C14 N2 . 1.3042(16) no C15 H15A . 0.9700 no C15 H15B . 0.9700 no C15 C16 . 1.524(2) no C16 H16A . 0.9600 no C16 H16B . 0.9600 no C16 H16C . 0.9600 no _cod_database_fobs_code 1557980