#------------------------------------------------------------------------------
#$Date: 2020-08-14 03:54:53 +0300 (Fri, 14 Aug 2020) $
#$Revision: 255302 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/88/1558844.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_1558844
loop_
_publ_author_name
'Avarvari, Narcis'
'Mroweh, Nabil'
'Mézière, Cécile'
'Allain, Magali'
'Auban-Senzier, Pascale'
'Canadell, Enric'
_publ_section_title
;
 Conservation of structural arrangements and 3:1 stoichiometry in a series
 of crystalline conductors of TMTTF, TMTSF, BEDT-TTF, and chiral
 DM-EDT-TTF with the oxo-bis[pentafluorotantalate(V)] dianion
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03665J
_journal_year                    2020
_chemical_formula_moiety         'C16 H36 N, F6 Ta'
_chemical_formula_sum            'C16 H36 F6 N Ta'
_chemical_formula_weight         537.41
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_date             2017-09-15T10:43:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-05-11 deposited with the CCDC.	2020-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.104(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8905(7)
_cell_length_b                   14.2131(7)
_cell_length_c                   15.3276(15)
_cell_measurement_reflns_used    3701
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.252
_cell_measurement_theta_min      4.156
_cell_volume                     2154.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 5.199
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.03
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5263
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        71
_diffrn_reflns_theta_max         72.63
_diffrn_reflns_theta_min         4.242
_exptl_absorpt_coefficient_mu    9.864
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.70558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_description       needle
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.039
_refine_diff_density_max         2.44
_refine_diff_density_min         -3.434
_refine_diff_density_rms         0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         5263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1117P)²+4.0562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1654
_refine_ls_wR_factor_ref         0.1771
_reflns_Friedel_coverage         0
_reflns_number_gt                4420
_reflns_number_total             5263
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc03665j2.cif
_cod_data_source_block           cp2016f
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1558844
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_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
C1 C 0.8124(9) 0.9301(7) 0.1807(6) 0.028(2) Uani 1 1 d . . . . .
H1A H 0.889509 0.922193 0.220086 0.033 Uiso 1 1 calc R U . . .
H1B H 0.844193 0.919912 0.122003 0.033 Uiso 1 1 calc R U . . .
C2 C 0.7098(10) 0.8521(9) 0.2009(7) 0.036(2) Uani 1 1 d . . . . .
H2A H 0.67932 0.858639 0.26032 0.043 Uiso 1 1 calc R U . . .
H2B H 0.631777 0.857671 0.161882 0.043 Uiso 1 1 calc R U . . .
C3 C 0.7746(11) 0.7583(9) 0.1894(8) 0.041(2) Uani 1 1 d . . . . .
H3A H 0.851078 0.752473 0.229559 0.049 Uiso 1 1 calc R U . . .
H3B H 0.807943 0.753089 0.13045 0.049 Uiso 1 1 calc R U . . .
C4 C 0.6734(13) 0.6786(9) 0.2061(8) 0.043(3) Uani 1 1 d . . . . .
H4A H 0.642557 0.682656 0.264966 0.064 Uiso 1 1 calc R U . . .
H4B H 0.716831 0.619038 0.197446 0.064 Uiso 1 1 calc R U . . .
H4C H 0.597732 0.684438 0.166318 0.064 Uiso 1 1 calc R U . . .
C5 C 0.7083(10) 1.0505(8) 0.2763(6) 0.033(2) Uani 1 1 d . . . . .
H5A H 0.689137 1.11737 0.279506 0.04 Uiso 1 1 calc R U . . .
H5B H 0.622461 1.017808 0.279791 0.04 Uiso 1 1 calc R U . . .
C6 C 0.7919(11) 1.0244(9) 0.3552(7) 0.039(3) Uani 1 1 d . . . . .
H6A H 0.877584 1.057532 0.354058 0.047 Uiso 1 1 calc R U . . .
H6B H 0.810369 0.957431 0.354423 0.047 Uiso 1 1 calc R U . . .
C7 C 0.7182(17) 1.0495(12) 0.4381(7) 0.060(4) Uani 1 1 d . . . . .
H7A H 0.707124 1.117289 0.440631 0.072 Uiso 1 1 calc R U . . .
H7B H 0.628769 1.021585 0.435649 0.072 Uiso 1 1 calc R U . . .
C8 C 0.791(2) 1.0169(13) 0.5204(9) 0.078(6) Uani 1 1 d . . . . .
H8A H 0.773635 0.951063 0.52908 0.117 Uiso 1 1 calc R U . . .
H8B H 0.758343 1.051809 0.569339 0.117 Uiso 1 1 calc R U . . .
H8C H 0.886153 1.026944 0.514983 0.117 Uiso 1 1 calc R U . . .
C9 C 0.6562(8) 1.0474(7) 0.1182(6) 0.0262(19) Uani 1 1 d . . . . .
H9A H 0.687022 1.022713 0.063071 0.031 Uiso 1 1 calc R U . . .
H9B H 0.577132 1.011402 0.134239 0.031 Uiso 1 1 calc R U . . .
C10 C 0.6134(10) 1.1481(9) 0.1042(7) 0.036(2) Uani 1 1 d . . . . .
H10A H 0.685742 1.182119 0.076252 0.043 Uiso 1 1 calc R U . . .
H10B H 0.598179 1.177369 0.160362 0.043 Uiso 1 1 calc R U . . .
C11 C 0.4850(11) 1.1559(10) 0.0481(7) 0.040(3) Uani 1 1 d . . . . .
H11A H 0.501064 1.128373 -0.008731 0.048 Uiso 1 1 calc R U . . .
H11B H 0.413365 1.120254 0.0751 0.048 Uiso 1 1 calc R U . . .
C12 C 0.4399(12) 1.2561(12) 0.0364(9) 0.049(3) Uani 1 1 d . . . . .
H12A H 0.440033 1.287039 0.092053 0.074 Uiso 1 1 calc R U . . .
H12B H 0.350269 1.257243 0.011291 0.074 Uiso 1 1 calc R U . . .
H12C H 0.500743 1.288056 -0.001668 0.074 Uiso 1 1 calc R U . . .
C13 C 0.8853(9) 1.0941(8) 0.1738(6) 0.0275(19) Uani 1 1 d . . . . .
H13A H 0.951609 1.081771 0.219845 0.033 Uiso 1 1 calc R U . . .
H13B H 0.855084 1.158617 0.180622 0.033 Uiso 1 1 calc R U . . .
C14 C 0.9556(10) 1.0858(9) 0.0860(7) 0.035(2) Uani 1 1 d . . . . .
H14A H 0.990571 1.022492 0.07958 0.042 Uiso 1 1 calc R U . . .
H14B H 0.889982 1.096663 0.039182 0.042 Uiso 1 1 calc R U . . .
C15 C 1.0702(11) 1.1554(9) 0.0782(8) 0.038(2) Uani 1 1 d . . . . .
H15A H 1.125527 1.136773 0.029532 0.046 Uiso 1 1 calc R U . . .
H15B H 1.126344 1.151713 0.130663 0.046 Uiso 1 1 calc R U . . .
C16 C 1.0274(13) 1.2573(11) 0.0648(11) 0.053(3) Uani 1 1 d . . . . .
H16A H 0.957931 1.260428 0.020301 0.08 Uiso 1 1 calc R U . . .
H16B H 1.103853 1.293845 0.047371 0.08 Uiso 1 1 calc R U . . .
H16C H 0.993264 1.2819 0.118437 0.08 Uiso 1 1 calc R U . . .
F1 F 0.2260(11) 0.8114(7) 0.2942(7) 0.079(3) Uani 1 1 d . . . . .
F2 F 0.2801(11) 0.9579(7) 0.0942(6) 0.072(3) Uani 1 1 d . . . . .
F3 F 0.4039(6) 0.9436(7) 0.2454(6) 0.058(2) Uani 1 1 d . . . . .
F4 F 0.3633(9) 0.7874(7) 0.1502(7) 0.066(2) Uani 1 1 d . . . . .
F5 F 0.1006(9) 0.8286(9) 0.1392(8) 0.086(4) Uani 1 1 d . . . . .
F6 F 0.1409(7) 0.9765(6) 0.2422(5) 0.0446(16) Uani 1 1 d . . . . .
N1 N 0.7666(9) 1.0304(6) 0.1870(5) 0.0273(15) Uani 1 1 d . . . . .
TA1 Ta 0.25348(5) 0.88355(3) 0.19521(3) 0.03098(19) Uani 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ta Ta -5.7959 5.2718 '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
N1 C1 C2 118.1(8) . . ?
N1 C1 H1A 107.8 . . ?
C2 C1 H1A 107.8 . . ?
N1 C1 H1B 107.8 . . ?
C2 C1 H1B 107.8 . . ?
H1A C1 H1B 107.1 . . ?
C3 C2 C1 109.5(8) . . ?
C3 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
C2 C3 C4 110.9(10) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 117.8(8) . . ?
C6 C5 H5A 107.9 . . ?
N1 C5 H5A 107.9 . . ?
C6 C5 H5B 107.9 . . ?
N1 C5 H5B 107.9 . . ?
H5A C5 H5B 107.2 . . ?
C5 C6 C7 110.5(9) . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 113.5(12) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 116.4(8) . . ?
C10 C9 H9A 108.2 . . ?
N1 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
N1 C9 H9B 108.2 . . ?
H9A C9 H9B 107.3 . . ?
C9 C10 C11 112.2(10) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 112.2(11) . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 116.2(8) . . ?
N1 C13 H13A 108.2 . . ?
C14 C13 H13A 108.2 . . ?
N1 C13 H13B 108.2 . . ?
C14 C13 H13B 108.2 . . ?
H13A C13 H13B 107.4 . . ?
C15 C14 C13 111.9(9) . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 115.2(10) . . ?
C14 C15 H15A 108.5 . . ?
C16 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 N1 C1 109.1(7) . . ?
C13 N1 C9 111.4(7) . . ?
C1 N1 C9 108.7(7) . . ?
C13 N1 C5 108.6(7) . . ?
C1 N1 C5 110.9(8) . . ?
C9 N1 C5 108.2(7) . . ?
F1 TA1 F3 92.5(5) . . ?
F1 TA1 F6 88.7(4) . . ?
F3 TA1 F6 89.7(3) . . ?
F1 TA1 F4 89.6(4) . . ?
F3 TA1 F4 91.3(4) . . ?
F6 TA1 F4 178.1(4) . . ?
F1 TA1 F5 90.8(6) . . ?
F3 TA1 F5 176.5(5) . . ?
F6 TA1 F5 89.4(4) . . ?
F4 TA1 F5 89.7(5) . . ?
F1 TA1 F2 179.5(4) . . ?
F3 TA1 F2 87.7(5) . . ?
F6 TA1 F2 90.8(4) . . ?
F4 TA1 F2 90.8(4) . . ?
F5 TA1 F2 89.0(6) . . ?
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
C1 N1 1.499(13) . ?
C1 C2 1.538(16) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C2 C3 1.491(17) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 C4 1.536(15) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C4 H4A 0.96 . ?
C4 H4B 0.96 . ?
C4 H4C 0.96 . ?
C5 C6 1.498(14) . ?
C5 N1 1.523(11) . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C6 C7 1.519(14) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.512(19) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C9 C10 1.507(16) . ?
C9 N1 1.523(11) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 C11 1.524(14) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 C12 1.50(2) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 N1 1.499(13) . ?
C13 C14 1.532(13) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 C15 1.512(15) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 C16 1.52(2) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
F1 TA1 1.856(8) . ?
F2 TA1 1.897(8) . ?
F3 TA1 1.868(7) . ?
F4 TA1 1.885(8) . ?
F5 TA1 1.893(9) . ?
F6 TA1 1.879(7) . ?
