#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/12/4501217.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_4501217
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Chopade, Prashant D.'
'Desper, John'
_publ_section_title
;
 Avoiding “Synthon Crossover” in Crystal Engineering with
 Halogen Bonds and Hydrogen Bonds
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5333
_journal_paper_doi               10.1021/cg2009013
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety
;
(C4 H5 N3)2 (C6 I2 F4)
;
_chemical_formula_sum            'C14 H10 F4 I2 N6'
_chemical_formula_weight         592.08
_chemical_name_systematic
;
PC-4-10e (2-aminopyrazine)2, 1,4-diiodotetrafluorobenzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 101.260(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.9013(6)
_cell_length_b                   5.6116(4)
_cell_length_c                   20.1258(16)
_cell_measurement_reflns_used    8154
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.40
_cell_measurement_theta_min      3.65
_cell_volume                     875.18(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10448
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         32.74
_diffrn_reflns_theta_min         4.13
_exptl_absorpt_coefficient_mu    3.645
_exptl_absorpt_correction_T_max  0.6688
_exptl_absorpt_correction_T_min  0.4749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.435
_refine_diff_density_min         -1.619
_refine_diff_density_rms         0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.739
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         3084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.739
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0336
_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)+(0.0200P)²+10.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0808
_reflns_number_gt                2633
_reflns_number_total             3084
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg2009013_si_003.cif
_cod_data_source_block           pc1010m_B1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        875.18(11)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4501217
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.69111(3) 0.21359(4) 0.651073(11) 0.02336(7) Uani 1 1 d .
C11 C 0.5766(4) 0.3837(6) 0.56083(17) 0.0232(6) Uani 1 1 d .
C12 C 0.5968(4) 0.2993(6) 0.49810(18) 0.0237(6) Uani 1 1 d .
F12 F 0.6910(3) 0.1017(4) 0.49390(11) 0.0300(5) Uani 1 1 d .
C16 C 0.4778(4) 0.5867(6) 0.56119(17) 0.0228(6) Uani 1 1 d .
F16 F 0.4518(3) 0.6783(4) 0.62035(11) 0.0275(4) Uani 1 1 d .
N21 N 0.8981(4) -0.1118(5) 0.91402(15) 0.0240(5) Uani 1 1 d .
C22 C 0.9594(4) 0.0913(6) 0.89235(18) 0.0238(6) Uani 1 1 d .
N22 N 1.0515(4) 0.2397(6) 0.93839(16) 0.0297(6) Uani 1 1 d .
H22A H 1.0705 0.2027 0.9817 0.036 Uiso 1 1 calc R
H22B H 1.0926 0.3734 0.9251 0.036 Uiso 1 1 calc R
C23 C 0.9265(5) 0.1465(7) 0.82230(17) 0.0246(6) Uani 1 1 d .
H23A H 0.9707 0.2908 0.8078 0.030 Uiso 1 1 calc R
N24 N 0.8368(4) 0.0038(6) 0.77667(15) 0.0270(6) Uani 1 1 d .
C25 C 0.7771(5) -0.2011(7) 0.79863(19) 0.0276(7) Uani 1 1 d .
H25A H 0.7130 -0.3088 0.7669 0.033 Uiso 1 1 calc R
C26 C 0.8085(5) -0.2550(6) 0.86650(19) 0.0253(6) Uani 1 1 d .
H26A H 0.7647 -0.4004 0.8804 0.030 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.02603(11) 0.02140(11) 0.02253(10) 0.00169(8) 0.00448(7) -0.00019(8)
C11 0.0262(15) 0.0208(15) 0.0225(14) 0.0020(11) 0.0043(11) -0.0011(12)
C12 0.0258(14) 0.0192(14) 0.0266(15) -0.0007(12) 0.0062(12) 0.0016(12)
F12 0.0384(12) 0.0232(10) 0.0287(10) 0.0013(8) 0.0072(9) 0.0092(9)
C16 0.0263(15) 0.0204(15) 0.0226(14) -0.0011(11) 0.0069(11) -0.0036(12)
F16 0.0354(11) 0.0253(11) 0.0226(9) -0.0024(8) 0.0078(8) 0.0012(8)
N21 0.0281(13) 0.0204(13) 0.0238(13) 0.0012(10) 0.0060(10) 0.0007(11)
C22 0.0239(14) 0.0229(16) 0.0247(15) 0.0021(12) 0.0054(12) 0.0026(12)
N22 0.0373(16) 0.0264(15) 0.0242(14) 0.0016(11) 0.0035(12) -0.0079(12)
C23 0.0309(16) 0.0215(15) 0.0222(14) 0.0029(12) 0.0072(12) 0.0020(13)
N24 0.0339(15) 0.0252(14) 0.0221(13) 0.0004(11) 0.0056(11) 0.0037(12)
C25 0.0339(17) 0.0242(16) 0.0243(15) -0.0020(13) 0.0044(13) 0.0002(14)
C26 0.0288(16) 0.0225(16) 0.0250(15) 0.0014(12) 0.0061(12) 0.0001(12)
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'
I I -0.4742 1.8119 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C11 I1 N24 176.77(12) . .
C16 C11 C12 116.9(3) . .
C16 C11 I1 121.3(2) . .
C12 C11 I1 121.8(3) . .
F12 C12 C16 118.4(3) . 3_666
F12 C12 C11 120.1(3) . .
C16 C12 C11 121.5(3) 3_666 .
F16 C16 C12 118.3(3) . 3_666
F16 C16 C11 120.2(3) . .
C12 C16 C11 121.6(3) 3_666 .
C26 N21 C22 116.8(3) . .
N21 C22 N22 118.7(3) . .
N21 C22 C23 120.1(3) . .
N22 C22 C23 121.2(3) . .
C22 N22 H22A 120.0 . .
C22 N22 H22B 120.0 . .
H22A N22 H22B 120.0 . .
N24 C23 C22 122.0(3) . .
N24 C23 H23A 119.0 . .
C22 C23 H23A 119.0 . .
C23 N24 C25 117.7(3) . .
C23 N24 I1 116.2(2) . .
C25 N24 I1 122.8(2) . .
N24 C25 C26 120.4(3) . .
N24 C25 H25A 119.8 . .
C26 C25 H25A 119.8 . .
N21 C26 C25 123.1(3) . .
N21 C26 H26A 118.5 . .
C25 C26 H26A 118.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C11 2.095(3) .
I1 N24 2.822(3) .
C11 C16 1.382(5) .
C11 C12 1.387(5) .
C12 F12 1.348(4) .
C12 C16 1.381(5) 3_666
C16 F16 1.349(4) .
C16 C12 1.381(5) 3_666
N21 C26 1.340(5) .
N21 C22 1.344(5) .
C22 N22 1.349(5) .
C22 C23 1.417(5) .
N22 H22A 0.8800 .
N22 H22B 0.8800 .
C23 N24 1.316(5) .
C23 H23A 0.9500 .
N24 C25 1.350(5) .
C25 C26 1.373(5) .
C25 H25A 0.9500 .
C26 H26A 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N22 H22A N21 0.88 2.13 3.006(4) 176.9 3_757
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
_geom_torsion_site_symmetry_4
C16 C11 C12 F12 -179.8(3) .
I1 C11 C12 F12 0.6(5) .
C16 C11 C12 C16 0.2(6) 3_666
I1 C11 C12 C16 -179.5(3) 3_666
C12 C11 C16 F16 179.6(3) .
I1 C11 C16 F16 -0.7(4) .
C12 C11 C16 C12 -0.2(6) 3_666
I1 C11 C16 C12 179.5(3) 3_666
C26 N21 C22 N22 -179.4(3) .
C26 N21 C22 C23 0.7(5) .
N21 C22 C23 N24 -0.1(5) .
N22 C22 C23 N24 -180.0(3) .
C22 C23 N24 C25 -0.6(5) .
C22 C23 N24 I1 159.3(3) .
C23 N24 C25 C26 0.7(5) .
I1 N24 C25 C26 -157.8(3) .
C22 N21 C26 C25 -0.6(5) .
N24 C25 C26 N21 -0.1(6) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144631
