#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/50/2235013.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_2235013
loop_
_publ_author_name
'Wang, Cui-Ping'
'Ma, Saiyong'
'Yu, Jiang-Long'
'Yan, Jing-Bo'
'Zhang, Zhi-Qiang'
_publ_section_title
;
 2-(4-Fluorophenyl)quinoxaline
;
_journal_coeditor_code           HB6725
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1779
_journal_paper_doi               10.1107/S1600536812017771
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H9 F N2'
_chemical_formula_moiety         'C14 H9 F N2'
_chemical_formula_sum            'C14 H9 F N2'
_chemical_formula_weight         224.23
_chemical_name_systematic
;
2-(4-Fluorophenyl)quinoxaline
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.866(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.249(13)
_cell_length_b                   3.7925(19)
_cell_length_c                   22.609(13)
_cell_measurement_reflns_used    3509
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.7
_cell_volume                     2078.1(19)
_computing_cell_refinement       'CrystalClear (Rigaku, 2008)'
_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.22
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9711
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.68
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2454
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0692P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1087
_reflns_number_gt                1797
_reflns_number_total             2454
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6725.cif
_cod_data_source_block           I
_cod_original_cell_volume        2078.2(19)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2235013
_cod_database_fobs_code          2235013
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
F F1 0.46580(3) 0.67692(19) 1.18737(3) 0.0321(2) Uani d . 1 1
N N1 0.39311(3) 0.1470(2) 0.93164(4) 0.0184(2) Uani d . 1 1
N N2 0.28374(3) -0.1127(2) 0.93193(4) 0.0213(2) Uani d . 1 1
C C1 0.36818(4) 0.0119(3) 0.88147(4) 0.0182(2) Uani d . 1 1
C C2 0.39774(4) -0.0011(3) 0.82863(5) 0.0216(3) Uani d . 1 1
H H2 0.4347 0.0813 0.8283 0.026 Uiso calc R 1 1
C C3 0.37306(5) -0.1322(3) 0.77801(5) 0.0238(3) Uani d . 1 1
H H3 0.3931 -0.1408 0.7426 0.029 Uiso calc R 1 1
C C4 0.31805(5) -0.2552(3) 0.77785(5) 0.0246(3) Uani d . 1 1
H H4 0.3013 -0.3434 0.7423 0.030 Uiso calc R 1 1
C C5 0.28877(4) -0.2481(3) 0.82842(5) 0.0226(3) Uani d . 1 1
H H5 0.2519 -0.3332 0.8280 0.027 Uiso calc R 1 1
C C6 0.31319(4) -0.1147(3) 0.88123(5) 0.0189(2) Uani d . 1 1
C C7 0.30886(4) 0.0153(3) 0.97928(5) 0.0205(2) Uani d . 1 1
H H7 0.2895 0.0180 1.0152 0.025 Uiso calc R 1 1
C C8 0.36398(4) 0.1514(3) 0.97994(5) 0.0175(2) Uani d . 1 1
C C9 0.38994(4) 0.2927(3) 1.03511(4) 0.0173(2) Uani d . 1 1
C C10 0.35866(4) 0.4178(3) 1.08148(5) 0.0204(3) Uani d . 1 1
H H10 0.3195 0.4132 1.0779 0.025 Uiso calc R 1 1
C C11 0.38416(5) 0.5485(3) 1.13269(5) 0.0217(3) Uani d . 1 1
H H11 0.3630 0.6352 1.1642 0.026 Uiso calc R 1 1
C C12 0.44101(5) 0.5499(3) 1.13683(5) 0.0217(3) Uani d . 1 1
C C13 0.47352(4) 0.4309(3) 1.09221(5) 0.0220(3) Uani d . 1 1
H H13 0.5126 0.4356 1.0963 0.026 Uiso calc R 1 1
C C14 0.44741(4) 0.3042(3) 1.04120(5) 0.0193(2) Uani d . 1 1
H H14 0.4690 0.2235 1.0096 0.023 Uiso calc R 1 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'
F F 0.0171 0.0103 '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
C8 N1 C1 117.21(9)
C7 N2 C6 116.44(10)
N1 C1 C2 119.44(10)
N1 C1 C6 121.36(10)
C2 C1 C6 119.20(10)
C3 C2 C1 119.98(11)
C3 C2 H2 120.0
C1 C2 H2 120.0
C2 C3 C4 120.63(10)
C2 C3 H3 119.7
C4 C3 H3 119.7
C5 C4 C3 120.52(10)
C5 C4 H4 119.7
C3 C4 H4 119.7
C4 C5 C6 120.05(10)
C4 C5 H5 120.0
C6 C5 H5 120.0
N2 C6 C5 119.65(10)
N2 C6 C1 120.73(10)
C5 C6 C1 119.61(10)
N2 C7 C8 123.50(10)
N2 C7 H7 118.3
C8 C7 H7 118.3
N1 C8 C7 120.74(10)
N1 C8 C9 118.54(10)
C7 C8 C9 120.71(9)
C14 C9 C10 118.67(10)
C14 C9 C8 119.37(9)
C10 C9 C8 121.96(10)
C11 C10 C9 120.66(10)
C11 C10 H10 119.7
C9 C10 H10 119.7
C12 C11 C10 118.41(10)
C12 C11 H11 120.8
C10 C11 H11 120.8
F1 C12 C13 118.89(10)
F1 C12 C11 118.13(10)
C13 C12 C11 122.98(10)
C12 C13 C14 117.86(10)
C12 C13 H13 121.1
C14 C13 H13 121.1
C13 C14 C9 121.40(10)
C13 C14 H14 119.3
C9 C14 H14 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C12 1.3617(13)
N1 C8 1.3198(14)
N1 C1 1.3676(14)
N2 C7 1.3078(15)
N2 C6 1.3703(14)
C1 C2 1.4138(16)
C1 C6 1.4171(16)
C2 C3 1.3676(16)
C2 H2 0.9500
C3 C4 1.4131(17)
C3 H3 0.9500
C4 C5 1.3656(16)
C4 H4 0.9500
C5 C6 1.4095(16)
C5 H5 0.9500
C7 C8 1.4325(15)
C7 H7 0.9500
C8 C9 1.4792(16)
C9 C14 1.3966(15)
C9 C10 1.3969(15)
C10 C11 1.3864(16)
C10 H10 0.9500
C11 C12 1.3787(17)
C11 H11 0.9500
C12 C13 1.3764(16)
C13 C14 1.3835(15)
C13 H13 0.9500
C14 H14 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C8 N1 C1 C2 -179.57(9)
C8 N1 C1 C6 0.65(15)
N1 C1 C2 C3 -179.32(10)
C6 C1 C2 C3 0.47(16)
C1 C2 C3 C4 0.10(17)
C2 C3 C4 C5 -0.63(17)
C3 C4 C5 C6 0.56(17)
C7 N2 C6 C5 -179.90(10)
C7 N2 C6 C1 0.90(15)
C4 C5 C6 N2 -179.19(10)
C4 C5 C6 C1 0.02(16)
N1 C1 C6 N2 -1.55(16)
C2 C1 C6 N2 178.67(9)
N1 C1 C6 C5 179.25(9)
C2 C1 C6 C5 -0.53(15)
C6 N2 C7 C8 0.53(16)
C1 N1 C8 C7 0.76(15)
C1 N1 C8 C9 179.40(9)
N2 C7 C8 N1 -1.44(17)
N2 C7 C8 C9 179.95(10)
N1 C8 C9 C14 -21.66(15)
C7 C8 C9 C14 156.99(10)
N1 C8 C9 C10 157.91(10)
C7 C8 C9 C10 -23.44(16)
C14 C9 C10 C11 -0.46(16)
C8 C9 C10 C11 179.97(10)
C9 C10 C11 C12 -0.40(16)
C10 C11 C12 F1 -179.66(10)
C10 C11 C12 C13 0.72(17)
F1 C12 C13 C14 -179.76(9)
C11 C12 C13 C14 -0.15(18)
C12 C13 C14 C9 -0.76(16)
C10 C9 C14 C13 1.06(16)
C8 C9 C14 C13 -179.36(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 645182
2 PubChem 738195
