#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/98/4509822.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4509822
loop_
_publ_author_name
'García, Marcos D.'
'Blanco, Víctor'
'Platas-Iglesias, Carlos'
'Peinador, Carlos'
'Quintela, José M.'
_publ_section_title
;
 Interplay between Halogen/Hydrogen Bonding and Electrostatic Interactions
 in 1,1′-Bis(4-iodobenzyl)-4,4′-bipyridine-1,1′-diium
 Salts
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5009
_journal_paper_doi               10.1021/cg901175e
_journal_volume                  9
_journal_year                    2009
_chemical_formula_sum            'C12 H10 F6 I N P'
_chemical_formula_weight         440.08
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 102.254(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   7.264(5)
_cell_length_b                   13.546(5)
_cell_length_c                   14.967(5)
_cell_measurement_reflns_used    5506
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      56.400
_cell_measurement_theta_min      5.823
_cell_volume                     1439.2(12)
_computing_cell_refinement
'SAINT V7.12A (Bruker Nonius 2004) in Apex2 suite'
_computing_data_collection       'Apex2  V.1.0-27 (Bruker Nonius, 2005)'
_computing_data_reduction
'SAINT and XPREP Version 6.14 COPYRIGHT(c) 2003 Bruker-AXS'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    "'SHELXL-97 (Sheldrick, 2008)"
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       'Omega scans + Phi 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  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18549
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    2.394
_exptl_absorpt_correction_T_max  0.9103
_exptl_absorpt_correction_T_min  0.7621
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.031
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.029
_refine_diff_density_min         -0.841
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0269
_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)+(0.0162P)²+1.4180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0490
_refine_ls_wR_factor_ref         0.0543
_reflns_number_gt                2815
_reflns_number_total             3554
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg901175esup1.cif
_cod_data_source_block           0933802_b1_0s
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4509822
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C12 C 0.8006(4) 0.0952(2) 0.8192(2) 0.0264(6) Uani 1 1 d
C11 C 0.8233(4) 0.0331(2) 0.8929(2) 0.0241(6) Uani 1 1 d
C10 C 0.9857(4) 0.03472(18) 0.96086(17) 0.0167(5) Uani 1 1 d
C9 C 1.1203(4) 0.1049(2) 0.95176(18) 0.0228(6) Uani 1 1 d
C8 C 1.0934(4) 0.1658(2) 0.87738(18) 0.0207(5) Uani 1 1 d
C7 C 0.9210(4) 0.2264(2) 0.7295(2) 0.0251(6) Uani 1 1 d
C1 C 0.4092(4) 0.18767(19) 0.53185(18) 0.0188(5) Uani 1 1 d
C6 C 0.5666(4) 0.1330(2) 0.5241(2) 0.0229(6) Uani 1 1 d
C5 C 0.7324(4) 0.14626(19) 0.5876(2) 0.0229(6) Uani 1 1 d
C4 C 0.7431(4) 0.21301(19) 0.65882(19) 0.0194(6) Uani 1 1 d
C3 C 0.5844(4) 0.26860(19) 0.66445(19) 0.0187(5) Uani 1 1 d
C2 C 0.4174(4) 0.2555(2) 0.60141(18) 0.0188(5) Uani 1 1 d
N1 N 0.9365(3) 0.15977(15) 0.81166(15) 0.0172(4) Uani 1 1 d
F1 F 0.3949(3) -0.07380(13) 0.83084(11) 0.0371(4) Uani 1 1 d
F2 F 0.4890(2) -0.03651(13) 0.70159(12) 0.0308(4) Uani 1 1 d
F3 F 0.3517(2) 0.08064(12) 0.77308(14) 0.0403(5) Uani 1 1 d
F4 F 0.1004(2) -0.02135(13) 0.76714(15) 0.0438(5) Uani 1 1 d
F5 F 0.2377(2) -0.13699(11) 0.69658(11) 0.0248(4) Uani 1 1 d
F6 F 0.1958(3) 0.01668(15) 0.63822(14) 0.0512(6) Uani 1 1 d
P1 P 0.29404(9) -0.02772(5) 0.73407(5) 0.01814(14) Uani 1 1 d
I1 I 0.15485(3) 0.165074(15) 0.437848(13) 0.02904(6) Uani 1 1 d
H12 H 0.702(4) 0.094(2) 0.774(2) 0.028(8) Uiso 1 1 d
H11 H 0.747(5) -0.009(3) 0.896(2) 0.044(10) Uiso 1 1 d
H9 H 1.232(5) 0.112(3) 0.996(2) 0.041(9) Uiso 1 1 d
H8 H 1.175(4) 0.211(2) 0.868(2) 0.024(8) Uiso 1 1 d
H7A H 1.017(5) 0.211(2) 0.707(2) 0.031(9) Uiso 1 1 d
H7B H 0.922(4) 0.294(3) 0.755(2) 0.034(9) Uiso 1 1 d
H6 H 0.557(4) 0.086(2) 0.4752(19) 0.017(7) Uiso 1 1 d
H5 H 0.829(5) 0.110(3) 0.586(2) 0.045(10) Uiso 1 1 d
H3 H 0.599(4) 0.309(2) 0.7121(19) 0.013(7) Uiso 1 1 d
H2 H 0.324(4) 0.293(2) 0.605(2) 0.020(7) Uiso 1 1 d
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'
P P 0.1023 0.0942 '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_3
N1 C12 C11 120.2(3) .
N1 C12 H12 117(2) .
C11 C12 H12 123(2) .
C12 C11 C10 121.3(3) .
C12 C11 H11 121(3) .
C10 C11 H11 117(3) .
C11 C10 C9 116.5(2) .
C11 C10 C10 121.7(3) 3_757
C9 C10 C10 121.9(3) 3_757
C8 C9 C10 120.7(3) .
C8 C9 H9 118(2) .
C10 C9 H9 121(2) .
N1 C8 C9 120.9(2) .
N1 C8 H8 114.8(19) .
C9 C8 H8 124.3(19) .
C4 C7 N1 114.0(2) .
C4 C7 H7A 110(2) .
N1 C7 H7A 105(2) .
C4 C7 H7B 108.5(19) .
N1 C7 H7B 104.3(19) .
H7A C7 H7B 116(3) .
C2 C1 C6 120.9(2) .
C2 C1 I1 119.66(19) .
C6 C1 I1 119.4(2) .
C5 C6 C1 119.2(3) .
C5 C6 H6 121.7(16) .
C1 C6 H6 119.1(16) .
C6 C5 C4 120.9(3) .
C6 C5 H5 121(2) .
C4 C5 H5 118(2) .
C5 C4 C3 119.1(3) .
C5 C4 C7 121.4(3) .
C3 C4 C7 119.5(3) .
C2 C3 C4 120.4(3) .
C2 C3 H3 124.6(17) .
C4 C3 H3 114.9(18) .
C1 C2 C3 119.5(2) .
C1 C2 H2 122(2) .
C3 C2 H2 118(2) .
C12 N1 C8 120.3(2) .
C12 N1 C7 121.9(2) .
C8 N1 C7 117.8(2) .
F6 P1 F4 90.18(12) .
F6 P1 F2 90.62(11) .
F4 P1 F2 178.78(11) .
F6 P1 F3 90.85(12) .
F4 P1 F3 90.97(9) .
F2 P1 F3 89.94(9) .
F6 P1 F1 179.34(12) .
F4 P1 F1 90.27(12) .
F2 P1 F1 88.92(10) .
F3 P1 F1 89.62(11) .
F6 P1 F5 90.07(11) .
F4 P1 F5 88.98(9) .
F2 P1 F5 90.09(9) .
F3 P1 F5 179.08(11) .
F1 P1 F5 89.46(9) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C12 N1 1.341(3) .
C12 C11 1.370(4) .
C12 H12 0.87(3) .
C11 C10 1.385(4) .
C11 H11 0.80(3) .
C10 C9 1.391(4) .
C10 C10 1.482(5) 3_757
C9 C8 1.366(4) .
C9 H9 0.93(3) .
C8 N1 1.341(3) .
C8 H8 0.89(3) .
C7 C4 1.498(4) .
C7 N1 1.509(3) .
C7 H7A 0.86(3) .
C7 H7B 0.99(3) .
C1 C2 1.380(4) .
C1 C6 1.387(4) .
C1 I1 2.094(3) .
C6 C5 1.378(4) .
C6 H6 0.96(3) .
C5 C4 1.387(4) .
C5 H5 0.86(4) .
C4 C3 1.394(4) .
C3 C2 1.381(4) .
C3 H3 0.89(3) .
C2 H2 0.86(3) .
F1 P1 1.6043(19) .
F2 P1 1.5966(18) .
F3 P1 1.6023(18) .
F4 P1 1.5895(19) .
F5 P1 1.6049(17) .
F6 P1 1.579(2) .
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_1
_geom_torsion_site_symmetry_4
N1 C12 C11 C10 -0.3(5) . .
C12 C11 C10 C9 2.3(4) . .
C12 C11 C10 C10 -177.8(3) . 3_757
C11 C10 C9 C8 -2.3(4) . .
C10 C10 C9 C8 177.7(3) 3_757 .
C10 C9 C8 N1 0.4(4) . .
C2 C1 C6 C5 0.8(4) . .
I1 C1 C6 C5 -178.24(19) . .
C1 C6 C5 C4 0.1(4) . .
C6 C5 C4 C3 -1.4(4) . .
C6 C5 C4 C7 178.6(2) . .
N1 C7 C4 C5 -90.5(3) . .
N1 C7 C4 C3 89.5(3) . .
C5 C4 C3 C2 1.7(4) . .
C7 C4 C3 C2 -178.2(2) . .
C6 C1 C2 C3 -0.4(4) . .
I1 C1 C2 C3 178.60(19) . .
C4 C3 C2 C1 -0.9(4) . .
C11 C12 N1 C8 -1.7(4) . .
C11 C12 N1 C7 177.2(3) . .
C9 C8 N1 C12 1.7(4) . .
C9 C8 N1 C7 -177.3(3) . .
C4 C7 N1 C12 -0.3(4) . .
C4 C7 N1 C8 178.7(2) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139147031
