#------------------------------------------------------------------------------
#$Date: 2021-06-05 21:08:54 +0300 (Sat, 05 Jun 2021) $
#$Revision: 265948 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/26/7242679.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_7242679
loop_
_publ_author_name
'Hossain, Anowar'
'Dey, Arka'
'Seth, Saikat Kumar'
'Ray, Partha Pratim'
'Ortega-Castro, Joaquín'
'Frontera, Antonio'
'Mukhopadhyay, Subrata'
_publ_section_title
;
 Anion-dependent structural variations and charge transport property
 analysis of
 4′-(3-pyridyl)-4,2′:6′,4′′-terpyridinium
 salts
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              3569
_journal_page_last               3581
_journal_paper_doi               10.1039/D1CE00248A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_sum            'C20 H19 Cl3 N4 O13'
_chemical_formula_weight         629.74
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2020-06-25 deposited with the CCDC.	2021-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                111.868(3)
_cell_angle_beta                 97.267(3)
_cell_angle_gamma                95.940(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9128(5)
_cell_length_b                   12.1194(7)
_cell_length_c                   14.6144(9)
_cell_measurement_reflns_used    3120
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.5
_cell_volume                     1272.82(14)
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_molecular_graphics
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13693
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.073
_diffrn_reflns_theta_max         25.073
_diffrn_reflns_theta_min         1.526
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.349
_refine_diff_density_min         -0.941
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0740
_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)+(0.1356P)²+2.2152P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2187
_refine_ls_wR_factor_ref         0.2272
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3873
_reflns_number_total             4470
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00248a2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7242677--7242679.cif.'
_cod_database_code               7242679
_shelx_shelxl_version_number     2018/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.65912(12) 0.13626(8) 0.30549(7) 0.0384(3) Uani 1 1 d . . . . .
Cl2 Cl 0.10918(15) 0.92634(10) 0.30675(10) 0.0550(4) Uani 1 1 d . . . . .
Cl3 Cl 0.2821(2) 0.66553(13) 0.96674(10) 0.0713(5) Uani 1 1 d . . . . .
O3 O 0.5791(4) 0.0245(3) 0.2257(2) 0.0516(8) Uani 1 1 d . . . . .
O4 O 0.7170(4) 0.1138(3) 0.3938(2) 0.0520(8) Uani 1 1 d . . . . .
N1 N 0.3032(4) 0.5156(3) 0.3982(2) 0.0311(7) Uani 1 1 d . . . . .
O2 O 0.8039(4) 0.1872(3) 0.2773(3) 0.0646(10) Uani 1 1 d . . . . .
O5 O 0.5376(5) 0.2182(3) 0.3281(3) 0.0635(10) Uani 1 1 d . . . . .
N2 N 0.6032(5) 0.8637(3) 0.3542(3) 0.0471(9) Uani 1 1 d . . . . .
H2A H 0.655425 0.933571 0.362653 0.057 Uiso 1 1 calc R U . . .
C9 C 0.2247(4) 0.4092(3) 0.3918(3) 0.0288(7) Uani 1 1 d . . . . .
N3 N 0.0880(5) 0.4090(3) 0.6618(3) 0.0478(9) Uani 1 1 d . . . . .
H3A H 0.061064 0.409021 0.716938 0.057 Uiso 1 1 calc R U . . .
C16 C 0.1747(5) 0.4080(3) 0.4865(3) 0.0306(7) Uani 1 1 d . . . . .
C8 C 0.3513(5) 0.5220(3) 0.3158(3) 0.0319(8) Uani 1 1 d . . . . .
N4 N 0.2495(5) -0.0047(3) 0.0546(3) 0.0521(9) Uani 1 1 d . . . . .
H4A H 0.264696 -0.070351 0.061920 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2325(5) 0.2024(3) 0.1274(3) 0.0365(8) Uani 1 1 d . . . . .
C6 C 0.2477(5) 0.3122(3) 0.2195(3) 0.0326(8) Uani 1 1 d . . . . .
C7 C 0.3260(5) 0.4230(3) 0.2251(3) 0.0359(8) Uani 1 1 d . . . . .
H7 H 0.360905 0.430905 0.169092 0.043 Uiso 1 1 calc R U . . .
C10 C 0.1942(5) 0.3063(3) 0.3046(3) 0.0319(8) Uani 1 1 d . . . . .
H10 H 0.138605 0.234050 0.303108 0.038 Uiso 1 1 calc R U . . .
C11 C 0.4397(5) 0.6427(3) 0.3277(3) 0.0335(8) Uani 1 1 d . . . . .
C17 C 0.0767(5) 0.3075(3) 0.4894(3) 0.0393(9) Uani 1 1 d . . . . .
H17 H 0.039927 0.238511 0.431155 0.047 Uiso 1 1 calc R U . . .
C20 C 0.2264(5) 0.5088(3) 0.5753(3) 0.0394(9) Uani 1 1 d . . . . .
H20 H 0.291553 0.577364 0.575439 0.047 Uiso 1 1 calc R U . . .
C5 C 0.2544(5) 0.0945(3) 0.1358(3) 0.0417(9) Uani 1 1 d . . . . .
H5 H 0.272651 0.091303 0.198802 0.050 Uiso 1 1 calc R U . . .
O8 O 0.2116(6) 0.8858(5) 0.3683(4) 0.0999(16) Uani 1 1 d . . . . .
C15 C 0.4958(5) 0.7312(3) 0.4232(3) 0.0391(9) Uani 1 1 d . . . . .
H15 H 0.477568 0.715817 0.479274 0.047 Uiso 1 1 calc R U . . .
C18 C 0.0349(6) 0.3103(4) 0.5777(3) 0.0479(10) Uani 1 1 d . . . . .
H18 H -0.030908 0.243304 0.579593 0.057 Uiso 1 1 calc R U . . .
C12 C 0.4688(6) 0.6694(4) 0.2469(3) 0.0466(10) Uani 1 1 d . . . . .
H12 H 0.433229 0.611327 0.182185 0.056 Uiso 1 1 calc R U . . .
C19 C 0.1820(6) 0.5079(4) 0.6625(3) 0.0464(10) Uani 1 1 d . . . . .
H19 H 0.216854 0.575571 0.721960 0.056 Uiso 1 1 calc R U . . .
C14 C 0.5785(6) 0.8420(4) 0.4339(3) 0.0463(10) Uani 1 1 d . . . . .
H14 H 0.617233 0.901799 0.497614 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2032(6) 0.2017(4) 0.0316(3) 0.0484(10) Uani 1 1 d . . . . .
H3 H 0.187762 0.272459 0.022892 0.058 Uiso 1 1 calc R U . . .
O7 O 0.1570(9) 1.0476(4) 0.3297(4) 0.1114(19) Uani 1 1 d . . . . .
C13 C 0.5510(6) 0.7827(4) 0.2620(4) 0.0523(11) Uani 1 1 d . . . . .
H13 H 0.569347 0.801626 0.207613 0.063 Uiso 1 1 calc R U . . .
C1 C 0.2218(6) -0.0058(5) -0.0382(3) 0.0590(13) Uani 1 1 d . . . . .
H1 H 0.219840 -0.076513 -0.093400 0.071 Uiso 1 1 calc R U . . .
O6 O 0.1558(8) 0.8655(5) 0.2061(4) 0.1113(18) Uani 1 1 d . . . . .
C2 C 0.1968(7) 0.0967(5) -0.0508(3) 0.0597(13) Uani 1 1 d . . . . .
H2 H 0.175357 0.096365 -0.114960 0.072 Uiso 1 1 calc R U . . .
O9 O -0.0634(6) 0.8853(6) 0.2920(5) 0.124(2) Uani 1 1 d . . . . .
O12 O 0.3682(11) 0.7708(6) 1.0427(5) 0.146(3) Uani 1 1 d . . . . .
O10 O 0.3691(10) 0.5915(7) 0.9010(6) 0.163(3) Uani 1 1 d . . . . .
O13 O 0.1900(12) 0.5952(7) 1.0072(5) 0.178(4) Uani 1 1 d . . . . .
O11 O 0.1532(12) 0.6924(9) 0.9049(7) 0.191(4) Uani 1 1 d . . . . .
O1 O 0.9792(8) 0.3939(4) 0.8238(3) 0.1074(19) Uani 1 1 d . . . . .
H1A H 0.901110 0.343217 0.828067 0.161 Uiso 1 1 d . U . . .
H1B H 0.968500 0.445400 0.861200 0.161 Uiso 1 1 d . U . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
O2 Cl1 O3 109.5(2) . . ?
O2 Cl1 O5 110.2(2) . . ?
O3 Cl1 O5 110.18(19) . . ?
O2 Cl1 O4 109.1(2) . . ?
O3 Cl1 O4 109.08(19) . . ?
O5 Cl1 O4 108.7(2) . . ?
O9 Cl2 O7 116.6(4) . . ?
O9 Cl2 O8 114.2(3) . . ?
O7 Cl2 O8 112.3(4) . . ?
O9 Cl2 O6 103.6(4) . . ?
O7 Cl2 O6 104.4(3) . . ?
O8 Cl2 O6 103.8(4) . . ?
O10 Cl3 O12 120.6(5) . . ?
O10 Cl3 O13 107.0(5) . . ?
O12 Cl3 O13 109.6(4) . . ?
O10 Cl3 O11 104.2(6) . . ?
O12 Cl3 O11 109.6(5) . . ?
O13 Cl3 O11 104.6(7) . . ?
C8 N1 C9 117.8(3) . . ?
C13 N2 C14 122.7(4) . . ?
C13 N2 H2A 118.7 . . ?
C14 N2 H2A 118.7 . . ?
N1 C9 C10 123.0(3) . . ?
N1 C9 C16 115.2(3) . . ?
C10 C9 C16 121.8(3) . . ?
C18 N3 C19 121.9(3) . . ?
C18 N3 H3A 119.0 . . ?
C19 N3 H3A 119.0 . . ?
C20 C16 C17 118.0(3) . . ?
C20 C16 C9 120.0(3) . . ?
C17 C16 C9 121.9(3) . . ?
N1 C8 C7 123.0(3) . . ?
N1 C8 C11 115.4(3) . . ?
C7 C8 C11 121.5(3) . . ?
C5 N4 C1 122.3(4) . . ?
C5 N4 H4A 118.8 . . ?
C1 N4 H4A 118.8 . . ?
C5 C4 C3 117.3(4) . . ?
C5 C4 C6 119.2(3) . . ?
C3 C4 C6 123.5(4) . . ?
C10 C6 C7 118.1(3) . . ?
C10 C6 C4 121.1(3) . . ?
C7 C6 C4 120.7(3) . . ?
C6 C7 C8 118.9(3) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C9 C10 C6 119.2(3) . . ?
C9 C10 H10 120.4 . . ?
C6 C10 H10 120.4 . . ?
C12 C11 C15 118.5(3) . . ?
C12 C11 C8 122.2(3) . . ?
C15 C11 C8 119.3(3) . . ?
C18 C17 C16 119.8(4) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C20 C16 120.3(4) . . ?
C19 C20 H20 119.9 . . ?
C16 C20 H20 119.9 . . ?
N4 C5 C4 120.7(4) . . ?
N4 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C14 C15 C11 119.2(4) . . ?
C14 C15 H15 120.4 . . ?
C11 C15 H15 120.4 . . ?
N3 C18 C17 120.3(4) . . ?
N3 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C11 C12 C13 119.9(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
N3 C19 C20 119.6(4) . . ?
N3 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
N2 C14 C15 120.2(4) . . ?
N2 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
N2 C13 C12 119.5(4) . . ?
N2 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
N4 C1 C2 119.5(4) . . ?
N4 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C1 C2 C3 119.9(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
H1A O1 H1B 100.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 O2 1.423(3) . ?
Cl1 O3 1.433(3) . ?
Cl1 O5 1.433(3) . ?
Cl1 O4 1.445(3) . ?
Cl2 O9 1.365(5) . ?
Cl2 O7 1.379(4) . ?
Cl2 O8 1.391(4) . ?
Cl2 O6 1.492(5) . ?
Cl3 O10 1.362(6) . ?
Cl3 O12 1.378(6) . ?
Cl3 O13 1.402(6) . ?
Cl3 O11 1.421(8) . ?
N1 C8 1.334(5) . ?
N1 C9 1.337(4) . ?
N2 C13 1.319(6) . ?
N2 C14 1.320(6) . ?
N2 H2A 0.8600 . ?
C9 C10 1.383(5) . ?
C9 C16 1.493(5) . ?
N3 C18 1.337(6) . ?
N3 C19 1.339(6) . ?
N3 H3A 0.8600 . ?
C16 C20 1.387(5) . ?
C16 C17 1.392(5) . ?
C8 C7 1.391(5) . ?
C8 C11 1.493(5) . ?
N4 C5 1.331(5) . ?
N4 C1 1.340(6) . ?
N4 H4A 0.8600 . ?
C4 C5 1.384(6) . ?
C4 C3 1.387(6) . ?
C4 C6 1.479(5) . ?
C6 C10 1.387(5) . ?
C6 C7 1.388(5) . ?
C7 H7 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.374(5) . ?
C11 C15 1.388(5) . ?
C17 C18 1.361(6) . ?
C17 H17 0.9300 . ?
C20 C19 1.369(6) . ?
C20 H20 0.9300 . ?
C5 H5 0.9300 . ?
C15 C14 1.375(6) . ?
C15 H15 0.9300 . ?
C18 H18 0.9300 . ?
C12 C13 1.382(6) . ?
C12 H12 0.9300 . ?
C19 H19 0.9300 . ?
C14 H14 0.9300 . ?
C3 C2 1.380(7) . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
C1 C2 1.352(8) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
O1 H1A 0.8499 . ?
O1 H1B 0.6810 . ?
