#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/75/2227568.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227568
loop_
_publ_author_name
'Arman, Hadi D.'
'Kaulgud, Trupta'
'Tiekink, Edward R. T.'
_publ_section_title
;
 1,2,4,5-Tetrafluoro-3,6-diiodobenzene--2,3-bis(pyridin-2-yl)pyrazine
 (1/1)
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2885
_journal_paper_doi               10.1107/S1600536810041668
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H10 N4, C6 F4 I2 '
_chemical_formula_moiety         'C14 H10 N4, C6 F4 I2 '
_chemical_formula_sum            'C20 H10 F4 I2 N4'
_chemical_formula_weight         636.04
_chemical_name_systematic
;
1,2,4,5-Tetrafluoro-3,6-diiodobenzene--2,3-bis(pyridin-2-yl)pyrazine (1/1)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.237(10)
_cell_angle_beta                 85.877(11)
_cell_angle_gamma                80.283(12)
_cell_formula_units_Z            2
_cell_length_a                   6.3997(15)
_cell_length_b                   10.737(2)
_cell_length_c                   15.092(4)
_cell_measurement_reflns_used    2870
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.8
_cell_volume                     983.3(4)
_computing_cell_refinement
'CrystalClear (Molecular Structure Corporation & Rigaku, 2005)'
_computing_data_collection
'CrystalClear (Molecular Structure Corporation & Rigaku, 2005)'
_computing_data_reduction
'CrystalClear (Molecular Structure Corporation & Rigaku, 2005)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      98(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Rigaku AFC12Κ/SATURN724'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_sigmaI/netI    0.033
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5074
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         2.7
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.250
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.148
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.32
_refine_diff_density_min         -1.20
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.09
_refine_ls_R_factor_all          0.041
_refine_ls_R_factor_gt           0.039
_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)+(0.0647P)²+2.2885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.106
_refine_ls_wR_factor_ref         0.109
_reflns_number_gt                3550
_reflns_number_total             3775
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5683.cif
_cod_data_source_block           I
_cod_database_code               2227568
_cod_database_fobs_code          2227568
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
I I1 0.02819(5) 0.31600(3) 0.57773(2) 0.02562(13) Uani d . 1 . .
I I2 0.78603(5) -0.24672(3) 0.69360(2) 0.02055(12) Uani d . 1 . .
F F1 0.0119(4) 0.0318(3) 0.7123(2) 0.0253(6) Uani d . 1 . .
F F2 0.2992(5) -0.1842(3) 0.7543(2) 0.0243(6) Uani d . 1 . .
F F3 0.7961(5) 0.0349(3) 0.5483(2) 0.0237(6) Uani d . 1 . .
F F4 0.5096(5) 0.2523(3) 0.5082(2) 0.0235(6) Uani d . 1 . .
C C1 0.2526(8) 0.1487(5) 0.6091(3) 0.0187(10) Uani d . 1 . .
C C2 0.2048(7) 0.0342(5) 0.6718(3) 0.0183(9) Uani d . 1 . .
C C3 0.3548(8) -0.0770(5) 0.6931(3) 0.0185(9) Uani d . 1 . .
C C4 0.5573(8) -0.0806(5) 0.6541(3) 0.0184(9) Uani d . 1 . .
C C5 0.6036(7) 0.0330(4) 0.5907(3) 0.0168(9) Uani d . 1 . .
C C6 0.4545(8) 0.1452(5) 0.5692(3) 0.0168(9) Uani d . 1 . .
N N1 0.4973(6) 0.6357(4) 0.3011(3) 0.0207(8) Uani d . 1 . .
N N2 0.8530(6) 0.4641(4) 0.2683(3) 0.0193(8) Uani d . 1 . .
N N3 0.7532(6) 0.8733(4) 0.1407(3) 0.0208(8) Uani d . 1 . .
N N4 0.8477(6) 0.6513(4) 0.0459(3) 0.0191(8) Uani d . 1 . .
C C7 0.6336(8) 0.6725(4) 0.2310(3) 0.0181(9) Uani d . 1 . .
C C8 0.5401(8) 0.5140(5) 0.3545(3) 0.0214(10) Uani d . 1 . .
H H8 0.4440 0.4842 0.4036 0.026 Uiso calc R 1 . .
C C9 0.7207(8) 0.4295(4) 0.3405(3) 0.0215(10) Uani d . 1 . .
H H9 0.7514 0.3457 0.3828 0.026 Uiso calc R 1 . .
C C10 0.8064(7) 0.5845(4) 0.2107(3) 0.0178(9) Uani d . 1 . .
C C11 0.5864(8) 0.8134(5) 0.1779(3) 0.0205(10) Uani d . 1 . .
C C12 0.7097(8) 1.0002(5) 0.0970(3) 0.0213(10) Uani d . 1 . .
H H12 0.8255 1.0442 0.0709 0.026 Uiso calc R 1 . .
C C13 0.5087(8) 1.0721(5) 0.0870(3) 0.0223(10) Uani d . 1 . .
H H13 0.4873 1.1624 0.0550 0.027 Uiso calc R 1 . .
C C14 0.3393(8) 1.0090(5) 0.1249(3) 0.0226(10) Uani d . 1 . .
H H14 0.1985 1.0552 0.1192 0.027 Uiso calc R 1 . .
C C15 0.3776(8) 0.8781(5) 0.1710(3) 0.0205(10) Uani d . 1 . .
H H15 0.2638 0.8327 0.1977 0.025 Uiso calc R 1 . .
C C16 0.9470(8) 0.6132(4) 0.1261(3) 0.0189(9) Uani d . 1 . .
C C17 0.9704(9) 0.6689(5) -0.0306(4) 0.0244(10) Uani d . 1 . .
H H17 0.9038 0.6948 -0.0884 0.029 Uiso calc R 1 . .
C C18 1.1934(8) 0.6509(5) -0.0298(4) 0.0241(10) Uani d . 1 . .
H H18 1.2751 0.6654 -0.0857 0.029 Uiso calc R 1 . .
C C19 1.2907(8) 0.6117(5) 0.0544(4) 0.0242(10) Uani d . 1 . .
H H19 1.4409 0.5979 0.0573 0.029 Uiso calc R 1 . .
C C20 1.1658(7) 0.5928(4) 0.1341(3) 0.0191(10) Uani d . 1 . .
H H20 1.2281 0.5665 0.1929 0.023 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 0.0030 0.0020 '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'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4740 1.8120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 '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
C6 C1 C2 . . 117.4(4) ?
C6 C1 I1 . . 121.8(4) ?
C2 C1 I1 . . 120.8(4) ?
F1 C2 C3 . . 119.2(4) ?
F1 C2 C1 . . 120.0(4) ?
C3 C2 C1 . . 120.8(4) ?
F2 C3 C2 . . 117.9(4) ?
F2 C3 C4 . . 120.1(4) ?
C2 C3 C4 . . 122.0(4) ?
C3 C4 C5 . . 117.1(4) ?
C3 C4 I2 . . 121.1(4) ?
C5 C4 I2 . . 121.7(4) ?
F3 C5 C6 . . 118.6(4) ?
F3 C5 C4 . . 120.1(4) ?
C6 C5 C4 . . 121.3(4) ?
F4 C6 C5 . . 118.5(4) ?
F4 C6 C1 . . 120.2(4) ?
C5 C6 C1 . . 121.4(4) ?
C8 N1 C7 . . 117.1(4) ?
C9 N2 C10 . . 117.8(4) ?
C12 N3 C11 . . 116.5(4) ?
C16 N4 C17 . . 116.7(4) ?
N1 C7 C10 . . 121.6(4) ?
N1 C7 C11 . . 114.6(4) ?
C10 C7 C11 . . 123.7(4) ?
N1 C8 C9 . . 121.9(4) ?
N1 C8 H8 . . 119.0 ?
C9 C8 H8 . . 119.0 ?
N2 C9 C8 . . 121.1(4) ?
N2 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
N2 C10 C7 . . 120.0(4) ?
N2 C10 C16 . . 115.6(4) ?
C7 C10 C16 . . 124.4(4) ?
N3 C11 C15 . . 122.8(4) ?
N3 C11 C7 . . 117.1(4) ?
C15 C11 C7 . . 120.1(4) ?
N3 C12 C13 . . 124.7(4) ?
N3 C12 H12 . . 117.6 ?
C13 C12 H12 . . 117.6 ?
C14 C13 C12 . . 118.1(4) ?
C14 C13 H13 . . 121.0 ?
C12 C13 H13 . . 121.0 ?
C13 C14 C15 . . 119.0(5) ?
C13 C14 H14 . . 120.5 ?
C15 C14 H14 . . 120.5 ?
C14 C15 C11 . . 118.9(4) ?
C14 C15 H15 . . 120.5 ?
C11 C15 H15 . . 120.5 ?
N4 C16 C20 . . 124.3(5) ?
N4 C16 C10 . . 115.5(4) ?
C20 C16 C10 . . 120.0(4) ?
N4 C17 C18 . . 123.3(5) ?
N4 C17 H17 . . 118.4 ?
C18 C17 H17 . . 118.4 ?
C19 C18 C17 . . 118.4(5) ?
C19 C18 H18 . . 120.8 ?
C17 C18 H18 . . 120.8 ?
C18 C19 C20 . . 118.9(5) ?
C18 C19 H19 . . 120.5 ?
C20 C19 H19 . . 120.5 ?
C16 C20 C19 . . 118.3(5) ?
C16 C20 H20 . . 120.8 ?
C19 C20 H20 . . 120.8 ?
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
I1 C1 . 2.068(5) ?
I2 C4 . 2.085(5) ?
F1 C2 . 1.339(5) ?
F2 C3 . 1.348(5) ?
F3 C5 . 1.348(5) ?
F4 C6 . 1.346(5) ?
C1 C6 . 1.385(7) ?
C1 C2 . 1.398(7) ?
C2 C3 . 1.378(7) ?
C3 C4 . 1.383(7) ?
C4 C5 . 1.392(7) ?
C5 C6 . 1.382(6) ?
N1 C8 . 1.331(6) ?
N1 C7 . 1.340(6) ?
N2 C9 . 1.340(7) ?
N2 C10 . 1.345(6) ?
N3 C12 . 1.333(6) ?
N3 C11 . 1.349(6) ?
N4 C16 . 1.338(6) ?
N4 C17 . 1.337(7) ?
C7 C10 . 1.402(7) ?
C7 C11 . 1.497(6) ?
C8 C9 . 1.385(7) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 C16 . 1.500(7) ?
C11 C15 . 1.395(7) ?
C12 C13 . 1.380(7) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.382(7) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.377(7) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 C20 . 1.389(6) ?
C17 C18 . 1.408(7) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.383(7) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.383(7) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
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
C8 H8 F4 . 0.95 2.54 3.145(6) 121
C9 H9 F4 . 0.95 2.46 3.100(6) 125
C18 H18 F2 1_664 0.95 2.52 3.341(7) 144
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
C6 C1 C2 F1 . . . . -179.7(4) ?
I1 C1 C2 F1 . . . . 0.1(6) ?
C6 C1 C2 C3 . . . . 0.6(7) ?
I1 C1 C2 C3 . . . . -179.6(4) ?
F1 C2 C3 F2 . . . . 0.1(7) ?
C1 C2 C3 F2 . . . . 179.8(4) ?
F1 C2 C3 C4 . . . . -179.6(4) ?
C1 C2 C3 C4 . . . . 0.1(7) ?
F2 C3 C4 C5 . . . . 179.3(4) ?
C2 C3 C4 C5 . . . . -1.0(7) ?
F2 C3 C4 I2 . . . . -3.4(6) ?
C2 C3 C4 I2 . . . . 176.3(4) ?
C3 C4 C5 F3 . . . . -178.1(4) ?
I2 C4 C5 F3 . . . . 4.6(6) ?
C3 C4 C5 C6 . . . . 1.2(7) ?
I2 C4 C5 C6 . . . . -176.1(3) ?
F3 C5 C6 F4 . . . . -1.4(6) ?
C4 C5 C6 F4 . . . . 179.2(4) ?
F3 C5 C6 C1 . . . . 178.8(4) ?
C4 C5 C6 C1 . . . . -0.6(7) ?
C2 C1 C6 F4 . . . . 179.9(4) ?
I1 C1 C6 F4 . . . . 0.0(6) ?
C2 C1 C6 C5 . . . . -0.3(7) ?
I1 C1 C6 C5 . . . . 179.9(4) ?
C8 N1 C7 C10 . . . . 4.1(7) ?
C8 N1 C7 C11 . . . . -175.5(4) ?
C7 N1 C8 C9 . . . . 2.0(7) ?
C10 N2 C9 C8 . . . . 1.1(7) ?
N1 C8 C9 N2 . . . . -4.8(8) ?
C9 N2 C10 C7 . . . . 4.8(7) ?
C9 N2 C10 C16 . . . . -174.1(4) ?
N1 C7 C10 N2 . . . . -7.7(7) ?
C11 C7 C10 N2 . . . . 171.8(4) ?
N1 C7 C10 C16 . . . . 171.1(4) ?
C11 C7 C10 C16 . . . . -9.4(7) ?
C12 N3 C11 C15 . . . . 0.7(7) ?
C12 N3 C11 C7 . . . . -177.3(4) ?
N1 C7 C11 N3 . . . . 148.1(4) ?
C10 C7 C11 N3 . . . . -31.5(7) ?
N1 C7 C11 C15 . . . . -29.9(7) ?
C10 C7 C11 C15 . . . . 150.5(5) ?
C11 N3 C12 C13 . . . . -0.5(7) ?
N3 C12 C13 C14 . . . . 0.0(8) ?
C12 C13 C14 C15 . . . . 0.3(7) ?
C13 C14 C15 C11 . . . . -0.1(7) ?
N3 C11 C15 C14 . . . . -0.4(8) ?
C7 C11 C15 C14 . . . . 177.5(5) ?
C17 N4 C16 C20 . . . . 0.8(7) ?
C17 N4 C16 C10 . . . . -175.5(4) ?
N2 C10 C16 N4 . . . . 124.0(4) ?
C7 C10 C16 N4 . . . . -54.8(6) ?
N2 C10 C16 C20 . . . . -52.5(6) ?
C7 C10 C16 C20 . . . . 128.7(5) ?
C16 N4 C17 C18 . . . . -0.8(7) ?
N4 C17 C18 C19 . . . . 0.8(7) ?
C17 C18 C19 C20 . . . . -0.6(7) ?
N4 C16 C20 C19 . . . . -0.6(7) ?
C10 C16 C20 C19 . . . . 175.5(4) ?
C18 C19 C20 C16 . . . . 0.5(7) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656245
