#------------------------------------------------------------------------------
#$Date: 2021-06-05 21:08:54 +0300 (Sat, 05 Jun 2021) $
#$Revision: 265948 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/26/7242677.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_7242677
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 Br3 N4 O'
_chemical_formula_weight         571.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 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                90
_cell_angle_beta                 97.220(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8625(6)
_cell_length_b                   27.236(3)
_cell_length_c                   16.031(2)
_cell_measurement_reflns_used    2560
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.5
_cell_volume                     2106.2(4)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0472
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13375
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.144
_diffrn_reflns_theta_min         1.969
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    5.764
_exptl_absorpt_correction_T_max  0.71
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.11(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         4642
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0353P)²+0.9192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3559
_reflns_number_total             4642
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00248a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7242677--7242679.cif.'
_cod_original_cell_volume        2106.2(5)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7242677
_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+1/2'
'x+1/2, y+1/2, 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_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
Br3 Br 0.47498(16) 0.54427(3) 0.18616(7) 0.0548(3) Uani 1 1 d . . . . .
Br2 Br 0.52614(18) 0.72522(4) 0.81399(7) 0.0590(3) Uani 1 1 d . . . . .
Br1 Br 0.92544(15) 0.94275(3) 0.37253(6) 0.0590(3) Uani 1 1 d . . . . .
N1 N 0.4683(13) 0.6282(2) 0.5265(4) 0.0341(13) Uani 1 1 d . . . . .
N2 N -0.1879(14) 0.5703(3) 0.7169(5) 0.0455(18) Uani 1 1 d . . . . .
H2A H -0.298064 0.553300 0.743374 0.055 Uiso 1 1 calc R U . . .
N4 N 0.6178(17) 0.8616(3) 0.4737(5) 0.060(2) Uani 1 1 d . . . . .
H4A H 0.704865 0.876907 0.438152 0.071 Uiso 1 1 calc R U . . .
C11 C 0.1472(14) 0.6250(3) 0.6297(5) 0.0311(17) Uani 1 1 d . . . . .
N3 N 1.0949(14) 0.5662(3) 0.3314(5) 0.050(2) Uani 1 1 d . . . . .
H3A H 1.198320 0.548327 0.303965 0.060 Uiso 1 1 calc R U . . .
C12 C -0.0023(18) 0.6467(3) 0.6880(6) 0.0421(19) Uani 1 1 d . . . . .
H12 H 0.010246 0.680310 0.697583 0.050 Uiso 1 1 calc R U . . .
C9 C 0.6196(14) 0.6534(3) 0.4758(5) 0.0316(16) Uani 1 1 d . . . . .
C15 C 0.1288(17) 0.5745(3) 0.6194(6) 0.0409(19) Uani 1 1 d . . . . .
H15 H 0.233757 0.558794 0.582721 0.049 Uiso 1 1 calc R U . . .
C10 C 0.6284(16) 0.7040(3) 0.4746(5) 0.0356(17) Uani 1 1 d . . . . .
H10 H 0.735176 0.719904 0.438663 0.043 Uiso 1 1 calc R U . . .
C14 C -0.045(2) 0.5477(3) 0.6635(6) 0.047(2) Uani 1 1 d . . . . .
H14 H -0.060990 0.513933 0.655717 0.057 Uiso 1 1 calc R U . . .
C7 C 0.3204(15) 0.7051(3) 0.5793(5) 0.0345(17) Uani 1 1 d . . . . .
H7 H 0.217757 0.721543 0.615854 0.041 Uiso 1 1 calc R U . . .
C8 C 0.3179(14) 0.6543(3) 0.5764(5) 0.0303(16) Uani 1 1 d . . . . .
C16 C 0.7846(15) 0.6231(3) 0.4233(5) 0.0365(18) Uani 1 1 d . . . . .
C18 C 1.1024(17) 0.6146(4) 0.3218(6) 0.049(2) Uani 1 1 d . . . . .
H18 H 1.209863 0.628497 0.283923 0.059 Uiso 1 1 calc R U . . .
C4 C 0.4814(16) 0.7856(3) 0.5274(5) 0.0346(16) Uani 1 1 d . . . . .
C6 C 0.4764(16) 0.7318(3) 0.5276(5) 0.0314(15) Uani 1 1 d . . . . .
C17 C 0.9486(17) 0.6444(3) 0.3689(6) 0.0433(19) Uani 1 1 d . . . . .
H17 H 0.955875 0.678392 0.363845 0.052 Uiso 1 1 calc R U . . .
C1 C 0.498(2) 0.8867(3) 0.5267(7) 0.057(3) Uani 1 1 d . . . . .
H1 H 0.506044 0.920822 0.526157 0.069 Uiso 1 1 calc R U . . .
C20 C 0.7768(17) 0.5723(3) 0.4286(5) 0.0406(19) Uani 1 1 d . . . . .
H20 H 0.665287 0.556998 0.463921 0.049 Uiso 1 1 calc R U . . .
C5 C 0.6123(19) 0.8120(3) 0.4718(6) 0.052(2) Uani 1 1 d . . . . .
H5 H 0.699624 0.795556 0.431621 0.062 Uiso 1 1 calc R U . . .
C13 C -0.1685(17) 0.6184(3) 0.7314(6) 0.047(2) Uani 1 1 d . . . . .
H13 H -0.267788 0.632687 0.770987 0.056 Uiso 1 1 calc R U . . .
C2 C 0.358(3) 0.8633(4) 0.5837(7) 0.074(3) Uani 1 1 d . . . . .
H2 H 0.269993 0.881207 0.622041 0.089 Uiso 1 1 calc R U . . .
C19 C 0.937(2) 0.5446(3) 0.3806(7) 0.054(2) Uani 1 1 d . . . . .
H19 H 0.933124 0.510479 0.383357 0.065 Uiso 1 1 calc R U . . .
O1 O 0.971(2) 0.7878(5) 0.7254(7) 0.114(3) Uani 1 1 d D . . . .
H1A H 1.137(12) 0.779(7) 0.734(12) 0.171 Uiso 1 1 d D U . . .
H1B H 0.85(2) 0.774(6) 0.749(11) 0.171 Uiso 1 1 d D U . . .
C3 C 0.349(2) 0.8130(3) 0.5839(6) 0.062(3) Uani 1 1 d . . . . .
H3 H 0.253204 0.796832 0.622386 0.075 Uiso 1 1 calc R 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'
Br Br -0.2901 2.4595 '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'
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
C9 N1 C8 117.7(6) . . ?
C14 N2 C13 122.7(7) . . ?
C14 N2 H2A 118.6 . . ?
C13 N2 H2A 118.6 . . ?
C1 N4 C5 122.5(8) . . ?
C1 N4 H4A 118.7 . . ?
C5 N4 H4A 118.7 . . ?
C12 C11 C15 118.1(7) . . ?
C12 C11 C8 122.4(7) . . ?
C15 C11 C8 119.5(7) . . ?
C19 N3 C18 123.0(7) . . ?
C19 N3 H3A 118.5 . . ?
C18 N3 H3A 118.5 . . ?
C13 C12 C11 119.8(8) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
N1 C9 C10 122.5(6) . . ?
N1 C9 C16 115.6(6) . . ?
C10 C9 C16 121.9(7) . . ?
C14 C15 C11 120.0(8) . . ?
C14 C15 H15 120.0 . . ?
C11 C15 H15 120.0 . . ?
C9 C10 C6 120.5(7) . . ?
C9 C10 H10 119.7 . . ?
C6 C10 H10 119.7 . . ?
N2 C14 C15 119.4(8) . . ?
N2 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C8 C7 C6 120.2(7) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
N1 C8 C7 122.9(7) . . ?
N1 C8 C11 116.0(6) . . ?
C7 C8 C11 121.1(6) . . ?
C17 C16 C20 118.7(7) . . ?
C17 C16 C9 121.4(7) . . ?
C20 C16 C9 120.0(7) . . ?
N3 C18 C17 119.5(8) . . ?
N3 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C5 C4 C3 115.8(8) . . ?
C5 C4 C6 122.5(7) . . ?
C3 C4 C6 121.7(7) . . ?
C7 C6 C10 116.2(6) . . ?
C7 C6 C4 122.1(7) . . ?
C10 C6 C4 121.7(7) . . ?
C16 C17 C18 119.4(8) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
N4 C1 C2 119.9(8) . . ?
N4 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C19 C20 C16 119.2(8) . . ?
C19 C20 H20 120.4 . . ?
C16 C20 H20 120.4 . . ?
N4 C5 C4 121.4(8) . . ?
N4 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
N2 C13 C12 119.9(8) . . ?
N2 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C1 C2 C3 119.1(9) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
N3 C19 C20 120.2(8) . . ?
N3 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
H1A O1 H1B 122(9) . . ?
C2 C3 C4 121.2(9) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
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
N1 C9 1.350(9) . ?
N1 C8 1.351(9) . ?
N2 C14 1.323(12) . ?
N2 C13 1.329(11) . ?
N2 H2A 0.8600 . ?
N4 C1 1.288(11) . ?
N4 C5 1.349(11) . ?
N4 H4A 0.8600 . ?
C11 C12 1.385(11) . ?
C11 C15 1.387(11) . ?
C11 C8 1.495(10) . ?
N3 C19 1.306(12) . ?
N3 C18 1.329(11) . ?
N3 H3A 0.8600 . ?
C12 C13 1.369(11) . ?
C12 H12 0.9300 . ?
C9 C10 1.377(10) . ?
C9 C16 1.484(10) . ?
C15 C14 1.376(13) . ?
C15 H15 0.9300 . ?
C10 C6 1.415(10) . ?
C10 H10 0.9300 . ?
C14 H14 0.9300 . ?
C7 C8 1.386(10) . ?
C7 C6 1.396(10) . ?
C7 H7 0.9300 . ?
C16 C17 1.381(11) . ?
C16 C20 1.388(11) . ?
C18 C17 1.389(12) . ?
C18 H18 0.9300 . ?
C4 C5 1.365(11) . ?
C4 C3 1.390(11) . ?
C4 C6 1.465(10) . ?
C17 H17 0.9300 . ?
C1 C2 1.363(13) . ?
C1 H1 0.9300 . ?
C20 C19 1.388(12) . ?
C20 H20 0.9300 . ?
C5 H5 0.9300 . ?
C13 H13 0.9300 . ?
C2 C3 1.372(13) . ?
C2 H2 0.9300 . ?
C19 H19 0.9300 . ?
O1 H1A 0.83(3) . ?
O1 H1B 0.84(3) . ?
C3 H3 0.9300 . ?
