#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$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       'ω 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/[σ²(Fo²)+(0.0756P)²+0.2732P] where P=(Fo²+2Fc²)/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>2σ(I)
_cod_data_source_file            hb4346sup1.cif
_cod_data_source_block           I
_cod_database_code               1557980
_cod_database_fobs_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_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
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 3700664
