#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:01:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178456 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/77/4027743.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_4027743
loop_
_publ_author_name
'Jinzhen Lu'
'Thanh Hai Le'
'Daouda A. K. Traore'
'Matthew C. J. Wilce'
'Alan M. Bond'
'Lisandra L. Martin'
_publ_contact_author_address
' School of Chemistry, Monash University, Clayton, Vic. 3800, Australia. '
_publ_contact_author_email
' alan.bond@monash.edu,lisa.martin@monash.edu'
_publ_contact_author_fax         61399054597
_publ_contact_author_name        'Prof Alan M Bond,A/Prof  Lisandra L Martin'
_publ_contact_author_phone       61399051338
_publ_section_title
;
 Synthetic Precursors for TCNQF42- Compounds: Synthesis, Characterization,
 and Electrochemical Studies of (Pr4N)2TCNQF4 and Li2TCNQF4
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10568
_journal_page_last               10574
_journal_paper_doi               10.1021/jo301403v
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C18 H28 F2 N3'
_chemical_formula_sum            'C18 H28 F2 N3'
_chemical_formula_weight         324.43
_chemical_name_common            TPA2TCNQF4
_chemical_name_systematic        TPA2TCNQF4
_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                 103.94(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.591(2)
_cell_length_b                   11.791(2)
_cell_length_c                   14.954(3)
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.63
_cell_volume                     1812.4(6)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       Blu-Ice
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'X-Seed (Barbour)'
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.77343
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11403
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9815
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   XDS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       block
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0445
_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)+(0.0372P)²+1.5387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1095
_reflns_number_gt                2902
_reflns_number_total             2478
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301403v_si_001.cif
_cod_data_source_block           c:\data\stufff~1\fromda~1\jl11\refine\mono
_cod_original_cell_volume        1812.5(6)
_cod_database_code               4027743
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
F1 F 0.76868(8) 0.56335(8) 0.02997(6) 0.0194(2) Uani 1 1 d .
F2 F 1.21859(8) 0.62530(8) 0.05809(6) 0.0195(2) Uani 1 1 d .
N3 N 0.98031(12) 0.15834(10) 0.20682(8) 0.0124(3) Uani 1 1 d .
N1 N 1.15281(14) 0.87263(12) 0.11864(10) 0.0246(3) Uani 1 1 d .
C4 C 0.99218(14) 0.60676(12) 0.04933(9) 0.0111(3) Uani 1 1 d .
N2 N 0.79808(14) 0.76267(12) 0.17365(11) 0.0270(4) Uani 1 1 d .
C5 C 0.88665(13) 0.53446(13) 0.01655(10) 0.0122(3) Uani 1 1 d .
C1 C 1.07888(15) 0.79832(13) 0.10880(10) 0.0147(3) Uani 1 1 d .
C3 C 0.98456(14) 0.71217(12) 0.09851(10) 0.0129(3) Uani 1 1 d .
C16 C 1.00348(16) 0.26210(13) 0.26873(10) 0.0170(3) Uani 1 1 d .
H16A H 1.0916 0.2567 0.3101 0.020 Uiso 1 1 calc R
H16B H 0.9401 0.2613 0.3078 0.020 Uiso 1 1 calc R
C2 C 0.88040(15) 0.73765(13) 0.13870(10) 0.0161(3) Uani 1 1 d .
C13 C 1.06995(14) 0.15784(13) 0.14108(10) 0.0145(3) Uani 1 1 d .
H13A H 1.0561 0.0861 0.1056 0.017 Uiso 1 1 calc R
H13B H 1.0438 0.2207 0.0966 0.017 Uiso 1 1 calc R
C6 C 1.10629(13) 0.56538(12) 0.02968(10) 0.0121(3) Uani 1 1 d .
C7 C 0.84041(14) 0.16323(13) 0.15032(10) 0.0159(3) Uani 1 1 d .
H7A H 0.7839 0.1795 0.1927 0.019 Uiso 1 1 calc R
H7B H 0.8324 0.2280 0.1072 0.019 Uiso 1 1 calc R
C10 C 1.00544(15) 0.05208(12) 0.26580(10) 0.0146(3) Uani 1 1 d .
H10A H 1.0972 0.0531 0.3015 0.018 Uiso 1 1 calc R
H10B H 0.9944 -0.0146 0.2244 0.018 Uiso 1 1 calc R
C8 C 0.78843(15) 0.05854(15) 0.09509(11) 0.0232(4) Uani 1 1 d .
H8A H 0.7827 -0.0053 0.1370 0.028 Uiso 1 1 calc R
H8B H 0.8472 0.0361 0.0557 0.028 Uiso 1 1 calc R
C11 C 0.91893(17) 0.03625(14) 0.33282(11) 0.0211(4) Uani 1 1 d .
H11A H 0.9349 0.0981 0.3789 0.025 Uiso 1 1 calc R
H11B H 0.8263 0.0391 0.2990 0.025 Uiso 1 1 calc R
C12 C 0.94875(17) -0.07774(14) 0.38120(11) 0.0215(4) Uani 1 1 d .
H12A H 0.9298 -0.1388 0.3355 0.032 Uiso 1 1 calc R
H12B H 0.8948 -0.0872 0.4255 0.032 Uiso 1 1 calc R
H12C H 1.0408 -0.0805 0.4137 0.032 Uiso 1 1 calc R
C17 C 0.9918(2) 0.37489(14) 0.21782(12) 0.0288(4) Uani 1 1 d .
H17A H 1.0629 0.3818 0.1856 0.035 Uiso 1 1 calc R
H17B H 0.9079 0.3780 0.1711 0.035 Uiso 1 1 calc R
C15 C 1.28608(17) 0.18581(17) 0.10941(13) 0.0302(4) Uani 1 1 d .
H15A H 1.2695 0.1208 0.0674 0.045 Uiso 1 1 calc R
H15B H 1.3797 0.1918 0.1370 0.045 Uiso 1 1 calc R
H15C H 1.2555 0.2554 0.0751 0.045 Uiso 1 1 calc R
C14 C 1.21400(15) 0.16942(15) 0.18507(11) 0.0223(4) Uani 1 1 d .
H14A H 1.2462 0.1004 0.2211 0.027 Uiso 1 1 calc R
H14B H 1.2293 0.2353 0.2274 0.027 Uiso 1 1 calc R
C18 C 0.9994(2) 0.47078(15) 0.28425(13) 0.0305(4) Uani 1 1 d .
H18A H 0.9312 0.4621 0.3179 0.046 Uiso 1 1 calc R
H18B H 0.9872 0.5428 0.2505 0.046 Uiso 1 1 calc R
H18C H 1.0848 0.4704 0.3280 0.046 Uiso 1 1 calc R
C9 C 0.65368(17) 0.08685(19) 0.03548(12) 0.0330(5) Uani 1 1 d .
H9A H 0.5990 0.1163 0.0745 0.050 Uiso 1 1 calc R
H9B H 0.6140 0.0182 0.0039 0.050 Uiso 1 1 calc R
H9C H 0.6616 0.1443 -0.0102 0.050 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'
N N 0.0061 0.0033 '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
C16 N3 C10 109.31(11) . .
C16 N3 C7 107.53(11) . .
C10 N3 C7 111.42(11) . .
C16 N3 C13 111.26(11) . .
C10 N3 C13 108.81(11) . .
C7 N3 C13 108.50(11) . .
C5 C4 C6 111.85(13) . .
C5 C4 C3 124.12(13) . .
C6 C4 C3 124.03(13) . .
F1 C5 C6 116.92(13) . 3_765
F1 C5 C4 118.85(13) . .
C6 C5 C4 124.23(13) 3_765 .
N1 C1 C3 176.89(16) . .
C1 C3 C2 114.04(13) . .
C1 C3 C4 123.18(13) . .
C2 C3 C4 122.77(13) . .
N3 C16 C17 114.66(12) . .
N3 C16 H16A 108.6 . .
C17 C16 H16A 108.6 . .
N3 C16 H16B 108.6 . .
C17 C16 H16B 108.6 . .
H16A C16 H16B 107.6 . .
N2 C2 C3 176.92(17) . .
C14 C13 N3 116.03(12) . .
C14 C13 H13A 108.3 . .
N3 C13 H13A 108.3 . .
C14 C13 H13B 108.3 . .
N3 C13 H13B 108.3 . .
H13A C13 H13B 107.4 . .
F2 C6 C5 116.87(12) . 3_765
F2 C6 C4 119.20(13) . .
C5 C6 C4 123.93(13) 3_765 .
C8 C7 N3 116.77(12) . .
C8 C7 H7A 108.1 . .
N3 C7 H7A 108.1 . .
C8 C7 H7B 108.1 . .
N3 C7 H7B 108.1 . .
H7A C7 H7B 107.3 . .
N3 C10 C11 115.73(12) . .
N3 C10 H10A 108.3 . .
C11 C10 H10A 108.3 . .
N3 C10 H10B 108.3 . .
C11 C10 H10B 108.3 . .
H10A C10 H10B 107.4 . .
C7 C8 C9 107.85(15) . .
C7 C8 H8A 110.1 . .
C9 C8 H8A 110.1 . .
C7 C8 H8B 110.1 . .
C9 C8 H8B 110.1 . .
H8A C8 H8B 108.5 . .
C12 C11 C10 109.38(13) . .
C12 C11 H11A 109.8 . .
C10 C11 H11A 109.8 . .
C12 C11 H11B 109.8 . .
C10 C11 H11B 109.8 . .
H11A C11 H11B 108.2 . .
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 . .
C18 C17 C16 110.09(14) . .
C18 C17 H17A 109.6 . .
C16 C17 H17A 109.6 . .
C18 C17 H17B 109.6 . .
C16 C17 H17B 109.6 . .
H17A C17 H17B 108.2 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C13 C14 C15 108.77(13) . .
C13 C14 H14A 109.9 . .
C15 C14 H14A 109.9 . .
C13 C14 H14B 109.9 . .
C15 C14 H14B 109.9 . .
H14A C14 H14B 108.3 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C5 1.3558(16) .
F2 C6 1.3604(17) .
N3 C16 1.5182(18) .
N3 C10 1.5185(18) .
N3 C7 1.5196(19) .
N3 C13 1.5222(18) .
N1 C1 1.161(2) .
C4 C5 1.397(2) .
C4 C6 1.399(2) .
C4 C3 1.456(2) .
N2 C2 1.157(2) .
C5 C6 1.376(2) 3_765
C1 C3 1.407(2) .
C3 C2 1.410(2) .
C16 C17 1.523(2) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C13 C14 1.515(2) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C6 C5 1.376(2) 3_765
C7 C8 1.513(2) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C10 C11 1.523(2) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C8 C9 1.526(2) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C11 C12 1.523(2) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C17 C18 1.494(2) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C15 C14 1.522(2) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
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_4
C6 C4 C5 F1 -179.70(12) .
C3 C4 C5 F1 0.6(2) .
C6 C4 C5 C6 -0.1(2) 3_765
C3 C4 C5 C6 -179.78(13) 3_765
N1 C1 C3 C2 -12(3) .
N1 C1 C3 C4 167(3) .
C5 C4 C3 C1 -161.95(14) .
C6 C4 C3 C1 18.4(2) .
C5 C4 C3 C2 16.9(2) .
C6 C4 C3 C2 -162.73(14) .
C10 N3 C16 C17 175.45(14) .
C7 N3 C16 C17 -63.44(16) .
C13 N3 C16 C17 55.25(17) .
C1 C3 C2 N2 -12(3) .
C4 C3 C2 N2 169(3) .
C16 N3 C13 C14 53.81(17) .
C10 N3 C13 C14 -66.69(16) .
C7 N3 C13 C14 171.92(13) .
C5 C4 C6 F2 -179.17(12) .
C3 C4 C6 F2 0.5(2) .
C5 C4 C6 C5 0.1(2) 3_765
C3 C4 C6 C5 179.78(13) 3_765
C16 N3 C7 C8 -170.09(12) .
C10 N3 C7 C8 -50.32(16) .
C13 N3 C7 C8 69.46(15) .
C16 N3 C10 C11 61.05(16) .
C7 N3 C10 C11 -57.67(16) .
C13 N3 C10 C11 -177.26(13) .
N3 C7 C8 C9 -173.36(13) .
N3 C10 C11 C12 175.66(13) .
N3 C16 C17 C18 172.76(15) .
N3 C13 C14 C15 -171.25(13) .
