#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/24/2222446.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_2222446
loop_
_publ_author_name
'Jahns, Hartmut'
'Koch, Pierre'
'Schollmeyer, Dieter'
'Laufer, Stefan'
_publ_section_title
;
 3-(4-Fluorophenyl)-6-methoxy-2-(4-pyridyl)quinoxaline
;
_journal_coeditor_code           SI2176
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1626
_journal_paper_doi               10.1107/S1600536809022119
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H14 F N3 O'
_chemical_formula_moiety         'C20 H14 F N3 O'
_chemical_formula_sum            'C20 H14 F N3 O'
_chemical_formula_weight         331.34
_chemical_name_systematic
;
3-(4-Fluorophenyl)-6-methoxy-2-(4-pyridyl)quinoxaline
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.3886(4)
_cell_length_b                   12.2071(8)
_cell_length_c                   34.562(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      69
_cell_measurement_theta_min      61
_cell_volume                     3117.3(6)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'CORINC (Dräger & Gattow, 1971)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'FR571 rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2950
_diffrn_reflns_theta_full        70.07
_diffrn_reflns_theta_max         70.07
_diffrn_reflns_theta_min         2.56
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.239
_refine_ls_extinction_coef       0.0024(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0436
_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/[σ²(Fo²)+(0.063P)²+1.8096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1155
_refine_ls_wR_factor_ref         0.1236
_reflns_number_gt                2542
_reflns_number_total             2950
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            si2176.cif
_cod_data_source_block           I
_cod_database_code               2222446
_cod_database_fobs_code          2222446
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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_disorder_assembly
_atom_site_disorder_group
C C1 0.0332(2) 0.08992(13) 0.65003(5) 0.0212(4) Uani d . 1 . .
C C2 0.1240(2) -0.01069(13) 0.64015(5) 0.0234(4) Uani d . 1 . .
N N3 0.1695(2) -0.08283(11) 0.66708(4) 0.0248(3) Uani d . 1 . .
C C4 0.1415(2) -0.05500(14) 0.70477(5) 0.0241(4) Uani d . 1 . .
C C5 0.1912(2) -0.12816(15) 0.73464(5) 0.0280(4) Uani d . 1 . .
H H5 0.2383 -0.1984 0.7284 0.034 Uiso calc R 1 . .
C C6 0.1717(3) -0.09798(15) 0.77228(5) 0.0290(4) Uani d . 1 . .
H H6 0.2040 -0.1478 0.7922 0.035 Uiso calc R 1 . .
C C7 0.1034(2) 0.00738(15) 0.78208(5) 0.0257(4) Uani d . 1 . .
C C8 0.0529(2) 0.07962(14) 0.75376(5) 0.0253(4) Uani d . 1 . .
H H8 0.0074 0.1499 0.7604 0.030 Uiso calc R 1 . .
C C9 0.0691(2) 0.04866(14) 0.71462(5) 0.0224(4) Uani d . 1 . .
N N10 0.01133(19) 0.11909(11) 0.68664(4) 0.0228(3) Uani d . 1 . .
C C11 -0.0457(2) 0.16507(13) 0.62087(5) 0.0214(4) Uani d . 1 . .
C C12 -0.0501(2) 0.27756(14) 0.62867(5) 0.0240(4) Uani d . 1 . .
H H12 0.0020 0.3047 0.6519 0.029 Uiso calc R 1 . .
C C13 -0.1297(3) 0.34958(14) 0.60292(5) 0.0277(4) Uani d . 1 . .
H H13 -0.1341 0.4258 0.6084 0.033 Uiso calc R 1 . .
C C14 -0.2026(2) 0.30841(15) 0.56913(5) 0.0277(4) Uani d . 1 . .
C C15 -0.2047(3) 0.19825(15) 0.56049(5) 0.0286(4) Uani d . 1 . .
H H15 -0.2590 0.1720 0.5374 0.034 Uiso calc R 1 . .
C C16 -0.1249(2) 0.12698(14) 0.58669(5) 0.0258(4) Uani d . 1 . .
H H16 -0.1240 0.0507 0.5813 0.031 Uiso calc R 1 . .
F F17 -0.27461(17) 0.37943(9) 0.54317(3) 0.0401(3) Uani d . 1 . .
C C18 0.1841(2) -0.03833(14) 0.60030(5) 0.0239(4) Uani d . 1 . .
C C19 0.1592(3) -0.14261(14) 0.58520(5) 0.0286(4) Uani d . 1 . .
H H19 0.0981 -0.1973 0.5998 0.034 Uiso calc R 1 . .
C C20 0.2249(3) -0.16553(15) 0.54863(5) 0.0340(4) Uani d . 1 . .
H H20 0.2038 -0.2367 0.5385 0.041 Uiso calc R 1 . .
N N21 0.3161(2) -0.09438(13) 0.52658(5) 0.0344(4) Uani d . 1 . .
C C22 0.3408(3) 0.00561(15) 0.54154(5) 0.0317(4) Uani d . 1 . .
H H22 0.4053 0.0580 0.5266 0.038 Uiso calc R 1 . .
C C23 0.2776(2) 0.03680(14) 0.57757(5) 0.0272(4) Uani d . 1 . .
H H23 0.2979 0.1091 0.5867 0.033 Uiso calc R 1 . .
O O24 0.09436(18) 0.02718(11) 0.82084(3) 0.0324(3) Uani d . 1 . .
C C25 0.0370(3) 0.13400(17) 0.83218(6) 0.0356(5) Uani d . 1 . .
H H25A 0.1183 0.1888 0.8209 0.053 Uiso calc R 1 . .
H H25B 0.0400 0.1398 0.8605 0.053 Uiso calc R 1 . .
H H25C -0.0866 0.1468 0.8230 0.053 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
N10 C1 C2 . . 120.82(15) ?
N10 C1 C11 . . 115.80(15) ?
C2 C1 C11 . . 123.35(15) ?
N3 C2 C1 . . 121.23(15) ?
N3 C2 C18 . . 115.13(15) ?
C1 C2 C18 . . 123.52(15) ?
C2 N3 C4 . . 117.89(15) ?
N3 C4 C5 . . 120.10(16) ?
N3 C4 C9 . . 120.69(15) ?
C5 C4 C9 . . 119.16(16) ?
C6 C5 C4 . . 120.00(17) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C5 C6 C7 . . 120.69(16) ?
C5 C6 H6 . . 119.7 ?
C7 C6 H6 . . 119.7 ?
O24 C7 C8 . . 125.10(17) ?
O24 C7 C6 . . 114.32(15) ?
C8 C7 C6 . . 120.58(16) ?
C7 C8 C9 . . 119.36(16) ?
C7 C8 H8 . . 120.3 ?
C9 C8 H8 . . 120.3 ?
N10 C9 C8 . . 119.04(15) ?
N10 C9 C4 . . 120.78(15) ?
C8 C9 C4 . . 120.17(15) ?
C1 N10 C9 . . 118.06(15) ?
C16 C11 C12 . . 118.64(16) ?
C16 C11 C1 . . 122.23(15) ?
C12 C11 C1 . . 119.03(15) ?
C13 C12 C11 . . 120.66(16) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C14 C13 C12 . . 118.61(16) ?
C14 C13 H13 . . 120.7 ?
C12 C13 H13 . . 120.7 ?
F17 C14 C15 . . 118.43(16) ?
F17 C14 C13 . . 118.67(16) ?
C15 C14 C13 . . 122.89(16) ?
C14 C15 C16 . . 117.77(17) ?
C14 C15 H15 . . 121.1 ?
C16 C15 H15 . . 121.1 ?
C15 C16 C11 . . 121.39(16) ?
C15 C16 H16 . . 119.3 ?
C11 C16 H16 . . 119.3 ?
C19 C18 C23 . . 117.26(16) ?
C19 C18 C2 . . 121.15(16) ?
C23 C18 C2 . . 121.47(15) ?
C20 C19 C18 . . 118.88(17) ?
C20 C19 H19 . . 120.6 ?
C18 C19 H19 . . 120.6 ?
N21 C20 C19 . . 124.49(17) ?
N21 C20 H20 . . 117.8 ?
C19 C20 H20 . . 117.8 ?
C20 N21 C22 . . 116.18(16) ?
N21 C22 C23 . . 123.54(17) ?
N21 C22 H22 . . 118.2 ?
C23 C22 H22 . . 118.2 ?
C22 C23 C18 . . 119.64(16) ?
C22 C23 H23 . . 120.2 ?
C18 C23 H23 . . 120.2 ?
C7 O24 C25 . . 116.56(14) ?
O24 C25 H25A . . 109.5 ?
O24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
O24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
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 N10 . 1.324(2) ?
C1 C2 . 1.440(2) ?
C1 C11 . 1.482(2) ?
C2 N3 . 1.325(2) ?
C2 C18 . 1.486(2) ?
N3 C4 . 1.362(2) ?
C4 C5 . 1.414(2) ?
C4 C9 . 1.416(2) ?
C5 C6 . 1.360(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.423(3) ?
C6 H6 . 0.9500 ?
C7 O24 . 1.363(2) ?
C7 C8 . 1.369(2) ?
C8 C9 . 1.410(2) ?
C8 H8 . 0.9500 ?
C9 N10 . 1.363(2) ?
C11 C16 . 1.398(2) ?
C11 C12 . 1.400(2) ?
C12 C13 . 1.382(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.381(3) ?
C13 H13 . 0.9500 ?
C14 F17 . 1.356(2) ?
C14 C15 . 1.378(3) ?
C15 C16 . 1.387(2) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C18 C19 . 1.388(2) ?
C18 C23 . 1.391(2) ?
C19 C20 . 1.382(3) ?
C19 H19 . 0.9500 ?
C20 N21 . 1.338(3) ?
C20 H20 . 0.9500 ?
N21 C22 . 1.338(2) ?
C22 C23 . 1.384(3) ?
C22 H22 . 0.9500 ?
C23 H23 . 0.9500 ?
O24 C25 . 1.426(2) ?
C25 H25A . 0.9800 ?
C25 H25B . 0.9800 ?
C25 H25C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C15 H15 N21 5_556 0.95 2.44 3.368(3) 165 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N10 C1 C2 N3 . . . . 7.9(3) ?
C11 C1 C2 N3 . . . . -170.22(16) ?
N10 C1 C2 C18 . . . . -167.94(16) ?
C11 C1 C2 C18 . . . . 13.9(3) ?
C1 C2 N3 C4 . . . . -5.4(2) ?
C18 C2 N3 C4 . . . . 170.78(15) ?
C2 N3 C4 C5 . . . . -178.67(16) ?
C2 N3 C4 C9 . . . . -1.1(2) ?
N3 C4 C5 C6 . . . . 176.67(16) ?
C9 C4 C5 C6 . . . . -1.0(3) ?
C4 C5 C6 C7 . . . . -0.7(3) ?
C5 C6 C7 O24 . . . . -178.82(16) ?
C5 C6 C7 C8 . . . . 1.2(3) ?
O24 C7 C8 C9 . . . . -179.94(15) ?
C6 C7 C8 C9 . . . . 0.0(3) ?
C7 C8 C9 N10 . . . . 177.21(16) ?
C7 C8 C9 C4 . . . . -1.7(3) ?
N3 C4 C9 N10 . . . . 5.7(3) ?
C5 C4 C9 N10 . . . . -176.72(16) ?
N3 C4 C9 C8 . . . . -175.42(15) ?
C5 C4 C9 C8 . . . . 2.2(3) ?
C2 C1 N10 C9 . . . . -3.2(2) ?
C11 C1 N10 C9 . . . . 175.05(14) ?
C8 C9 N10 C1 . . . . 177.83(15) ?
C4 C9 N10 C1 . . . . -3.2(2) ?
N10 C1 C11 C16 . . . . -143.69(17) ?
C2 C1 C11 C16 . . . . 34.5(2) ?
N10 C1 C11 C12 . . . . 32.8(2) ?
C2 C1 C11 C12 . . . . -149.01(16) ?
C16 C11 C12 C13 . . . . -0.6(3) ?
C1 C11 C12 C13 . . . . -177.19(16) ?
C11 C12 C13 C14 . . . . -0.8(3) ?
C12 C13 C14 F17 . . . . -177.56(16) ?
C12 C13 C14 C15 . . . . 2.1(3) ?
F17 C14 C15 C16 . . . . 177.79(16) ?
C13 C14 C15 C16 . . . . -1.9(3) ?
C14 C15 C16 C11 . . . . 0.4(3) ?
C12 C11 C16 C15 . . . . 0.8(3) ?
C1 C11 C16 C15 . . . . 177.30(16) ?
N3 C2 C18 C19 . . . . 46.7(2) ?
C1 C2 C18 C19 . . . . -137.24(18) ?
N3 C2 C18 C23 . . . . -129.12(18) ?
C1 C2 C18 C23 . . . . 47.0(3) ?
C23 C18 C19 C20 . . . . -1.1(3) ?
C2 C18 C19 C20 . . . . -177.09(17) ?
C18 C19 C20 N21 . . . . 1.7(3) ?
C19 C20 N21 C22 . . . . -1.0(3) ?
C20 N21 C22 C23 . . . . -0.1(3) ?
N21 C22 C23 C18 . . . . 0.6(3) ?
C19 C18 C23 C22 . . . . 0.1(3) ?
C2 C18 C23 C22 . . . . 176.04(17) ?
C8 C7 O24 C25 . . . . -3.7(3) ?
C6 C7 O24 C25 . . . . 176.37(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24630571
