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#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/17/7211718.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_7211718
loop_
_publ_author_name
'Cauliez, Pascal'
'Polo, Victor'
'Roisnel, Thierry'
'Llusar, Rosa'
'Fourmigué, Marc'
_publ_section_title
;
 The thiocyanate anion as a polydentate halogen bond acceptor
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              558
_journal_paper_doi               10.1039/b913559f
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C16 H36 N, C6 F4 I2, C N S'
_chemical_formula_sum            'C23 H36 F4 I2 N2 S'
_chemical_formula_weight         702.40
_chemical_name_systematic
;
tetrabutylammonium thiocyanate, 1,4-diiodotetrafluorobenzene
;
_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                90.00
_cell_angle_beta                 93.2206(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0837(7)
_cell_length_b                   22.4174(14)
_cell_length_c                   12.9033(8)
_cell_measurement_reflns_used    8336
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.05
_cell_measurement_theta_min      2.22
_cell_volume                     2912.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 -Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            61852
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    2.270
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.7200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         6715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0317
_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)+(0.0247P)²+2.1970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0738
_reflns_number_gt                4588
_reflns_number_total             6715
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b913559f.txt
_cod_data_source_block           jbb49d
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7211718
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.49354(2) 0.093025(10) 0.916492(18) 0.06832(9) Uani 1 1 d . . .
I2 I 0.89066(3) -0.134521(11) 0.72930(2) 0.07653(9) Uani 1 1 d . . .
F1 F 0.7538(2) 0.02551(11) 1.01588(16) 0.0991(7) Uani 1 1 d . . .
F2 F 0.9036(3) -0.06168(12) 0.94606(19) 0.1076(8) Uani 1 1 d . . .
F3 F 0.6376(2) -0.06642(11) 0.63565(16) 0.0997(8) Uani 1 1 d . . .
F4 F 0.4888(2) 0.01980(10) 0.70493(17) 0.0928(7) Uani 1 1 d . . .
C1 C 0.6161(3) 0.02544(14) 0.8632(2) 0.0598(8) Uani 1 1 d . . .
C2 C 0.7233(4) 0.00300(16) 0.9212(2) 0.0679(9) Uani 1 1 d . . .
C3 C 0.8005(4) -0.04173(16) 0.8856(3) 0.0699(9) Uani 1 1 d . . .
C4 C 0.7754(3) -0.06660(15) 0.7893(3) 0.0637(8) Uani 1 1 d . . .
C5 C 0.6689(4) -0.04443(16) 0.7311(3) 0.0692(9) Uani 1 1 d . . .
C6 C 0.5917(4) 0.00037(16) 0.7667(3) 0.0660(9) Uani 1 1 d . . .
S1 S 0.29537(11) 0.20017(5) 0.97725(10) 0.0905(3) Uani 1 1 d . . .
N1 N 0.4690(4) 0.27635(18) 0.8866(3) 0.1037(12) Uani 1 1 d . . .
C7 C 0.3970(4) 0.24595(17) 0.9252(3) 0.0668(9) Uani 1 1 d . . .
N2 N 0.3178(2) 0.21179(11) 0.58491(17) 0.0553(6) Uani 1 1 d . B .
C8 C 0.4590(3) 0.19608(15) 0.6223(2) 0.0611(8) Uani 1 1 d . . .
H8A H 0.5092 0.2328 0.6307 0.073 Uiso 1 1 calc R . .
H8B H 0.4564 0.1779 0.6904 0.073 Uiso 1 1 calc R . .
C9 C 0.5333(3) 0.15482(19) 0.5538(3) 0.0754(10) Uani 1 1 d . . .
H9A H 0.5425 0.1734 0.4867 0.090 Uiso 1 1 calc R . .
H9B H 0.4836 0.1181 0.5430 0.090 Uiso 1 1 calc R . .
C10 C 0.6690(4) 0.1410(2) 0.6031(3) 0.0907(12) Uani 1 1 d . . .
H10A H 0.7191 0.1778 0.6113 0.109 Uiso 1 1 calc R . .
H10B H 0.6591 0.1244 0.6716 0.109 Uiso 1 1 calc R . .
C11 C 0.7457(5) 0.0978(3) 0.5405(5) 0.142(2) Uani 1 1 d . . .
H11A H 0.8315 0.0911 0.5745 0.213 Uiso 1 1 calc R . .
H11B H 0.7563 0.1141 0.4726 0.213 Uiso 1 1 calc R . .
H11C H 0.6984 0.0607 0.5343 0.213 Uiso 1 1 calc R . .
C12 C 0.3159(4) 0.24418(17) 0.4816(2) 0.0694(10) Uani 1 1 d . . .
H12A H 0.3521 0.2176 0.4310 0.083 Uiso 1 1 calc R A 1
H12B H 0.2240 0.2518 0.4593 0.083 Uiso 1 1 calc R A 1
C13A C 0.3902(4) 0.3022(2) 0.4791(3) 0.0897(12) Uani 0.50 1 d P B 1
H13A H 0.4846 0.2955 0.4926 0.108 Uiso 0.50 1 calc PR B 1
H13B H 0.3595 0.3293 0.5312 0.108 Uiso 0.50 1 calc PR B 1
C14A C 0.3630(11) 0.3277(10) 0.3717(14) 0.113(8) Uani 0.52(6) 1 d P B 1
H14A H 0.2703 0.3198 0.3525 0.136 Uiso 0.52(6) 1 calc PR B 1
H14B H 0.3718 0.3707 0.3781 0.136 Uiso 0.52(6) 1 calc PR B 1
C15A C 0.421(2) 0.3141(11) 0.3031(13) 0.146(9) Uani 0.374(13) 1 d P B 1
H15A H 0.3929 0.3374 0.2436 0.218 Uiso 0.374(13) 1 calc PR B 1
H15B H 0.4061 0.2726 0.2884 0.218 Uiso 0.374(13) 1 calc PR B 1
H15C H 0.5142 0.3206 0.3192 0.218 Uiso 0.374(13) 1 calc PR B 1
C13B C 0.3902(4) 0.3022(2) 0.4791(3) 0.0897(12) Uani 0.50 1 d P B 2
H13C H 0.4819 0.2958 0.5033 0.108 Uiso 0.50 1 calc PR B 2
H13D H 0.3512 0.3305 0.5253 0.108 Uiso 0.50 1 calc PR B 2
C14B C 0.385(4) 0.3281(11) 0.367(2) 0.198(17) Uani 0.48(6) 1 d P B 2
H14C H 0.4247 0.2984 0.3234 0.237 Uiso 0.48(6) 1 calc PR B 2
H14D H 0.2924 0.3311 0.3439 0.237 Uiso 0.48(6) 1 calc PR B 2
C15B C 0.4398(9) 0.3785(5) 0.3472(7) 0.110(4) Uani 0.626(13) 1 d P B 2
H15D H 0.4235 0.3879 0.2751 0.166 Uiso 0.626(13) 1 calc PR B 2
H15E H 0.5337 0.3760 0.3632 0.166 Uiso 0.626(13) 1 calc PR B 2
H15F H 0.4026 0.4092 0.3887 0.166 Uiso 0.626(13) 1 calc PR B 2
C16 C 0.2343(3) 0.15669(16) 0.5665(3) 0.0673(9) Uani 1 1 d . . .
H16A H 0.2701 0.1344 0.5100 0.081 Uiso 1 1 calc R B .
H16B H 0.1452 0.1691 0.5437 0.081 Uiso 1 1 calc R . .
C17 C 0.2243(4) 0.11518(17) 0.6577(3) 0.0837(11) Uani 1 1 d . B .
H17A H 0.1788 0.1351 0.7122 0.100 Uiso 1 1 calc R . .
H17B H 0.3126 0.1044 0.6850 0.100 Uiso 1 1 calc R . .
C18 C 0.1481(5) 0.0591(2) 0.6236(5) 0.136(2) Uani 1 1 d . . .
H18A H 0.0614 0.0707 0.5941 0.164 Uiso 1 1 calc R B .
H18B H 0.1950 0.0396 0.5694 0.164 Uiso 1 1 calc R . .
C19 C 0.1304(7) 0.0161(3) 0.7074(7) 0.205(4) Uani 1 1 d . B .
H19A H 0.0836 -0.0183 0.6800 0.307 Uiso 1 1 calc R . .
H19B H 0.0802 0.0343 0.7600 0.307 Uiso 1 1 calc R . .
H19C H 0.2157 0.0041 0.7371 0.307 Uiso 1 1 calc R . .
C20 C 0.2624(3) 0.25064(15) 0.6683(2) 0.0655(9) Uani 1 1 d . . .
H20A H 0.3215 0.2844 0.6802 0.079 Uiso 1 1 calc R B .
H20B H 0.2636 0.2278 0.7322 0.079 Uiso 1 1 calc R . .
C21 C 0.1229(4) 0.27428(18) 0.6458(3) 0.0811(11) Uani 1 1 d . B .
H21A H 0.0610 0.2412 0.6396 0.097 Uiso 1 1 calc R . .
H21B H 0.1187 0.2957 0.5804 0.097 Uiso 1 1 calc R . .
C22 C 0.0835(5) 0.3158(2) 0.7325(3) 0.0985(14) Uani 1 1 d . . .
H22A H -0.0110 0.3238 0.7234 0.118 Uiso 1 1 calc R B .
H22B H 0.0991 0.2955 0.7984 0.118 Uiso 1 1 calc R . .
C23 C 0.1544(6) 0.3726(2) 0.7371(4) 0.1282(19) Uani 1 1 d . B .
H23A H 0.1248 0.3959 0.7938 0.192 Uiso 1 1 calc R . .
H23B H 0.1368 0.3939 0.6733 0.192 Uiso 1 1 calc R . .
H23C H 0.2480 0.3653 0.7472 0.192 Uiso 1 1 calc R . .
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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C2 C1 C6 116.0(3)
C2 C1 I1 123.1(2)
C6 C1 I1 120.9(3)
F1 C2 C3 118.5(3)
F1 C2 C1 119.4(3)
C3 C2 C1 122.1(3)
F2 C3 C2 119.2(3)
F2 C3 C4 119.2(3)
C2 C3 C4 121.6(3)
C5 C4 C3 116.6(3)
C5 C4 I2 119.8(2)
C3 C4 I2 123.6(3)
F3 C5 C6 117.9(3)
F3 C5 C4 120.3(3)
C6 C5 C4 121.8(3)
F4 C6 C5 118.3(3)
F4 C6 C1 119.8(3)
C5 C6 C1 121.9(3)
N1 C7 S1 177.7(4)
C16 N2 C20 111.0(3)
C16 N2 C12 105.9(2)
C20 N2 C12 111.2(2)
C16 N2 C8 111.5(2)
C20 N2 C8 106.5(2)
C12 N2 C8 110.9(2)
C9 C8 N2 116.3(3)
C8 C9 C10 110.3(3)
C11 C10 C9 112.8(4)
C13A C12 N2 116.8(3)
C12 C13A C14A 106.5(9)
C15A C14A C13A 122.6(14)
N2 C16 C17 116.4(3)
C16 C17 C18 109.8(4)
C19 C18 C17 114.2(6)
N2 C20 C21 116.1(3)
C20 C21 C22 110.5(3)
C23 C22 C21 114.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.095(3)
I2 C4 2.090(3)
F1 C2 1.341(4)
F2 C3 1.341(4)
F3 C5 1.348(4)
F4 C6 1.345(4)
C1 C2 1.375(5)
C1 C6 1.376(4)
C2 C3 1.365(5)
C3 C4 1.373(5)
C4 C5 1.368(5)
C5 C6 1.366(5)
S1 C7 1.623(4)
N1 C7 1.131(5)
N2 C16 1.507(4)
N2 C20 1.515(4)
N2 C12 1.517(4)
N2 C8 1.519(4)
C8 C9 1.508(5)
C9 C10 1.508(5)
C10 C11 1.503(6)
C12 C13A 1.502(5)
C13A C14A 1.511(15)
C14A C15A 1.13(2)
C14B C15B 1.29(3)
C16 C17 1.508(5)
C17 C18 1.525(6)
C18 C19 1.467(8)
C20 C21 1.516(5)
C21 C22 1.524(5)
C22 C23 1.459(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139197395
