#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/55/1505543.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_1505543
loop_
_publ_author_name
'Tanabe, Kana'
'Yasuda, Takuma'
'Yoshio, Masafumi'
'Kato, Takashi'
_publ_section_title
;
 Viologen-based redox-active ionic liquid crystals forming columnar
 phases.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4271
_journal_page_last               4274
_journal_paper_doi               10.1021/ol701741e
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C18 H23 F6 N O4 P'
_chemical_formula_weight         462.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.942(11)
_cell_angle_beta                 106.273(12)
_cell_angle_gamma                96.624(11)
_cell_formula_units_Z            2
_cell_length_a                   7.6121(18)
_cell_length_b                   11.628(4)
_cell_length_c                   12.241(4)
_cell_measurement_reflns_used    2862
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      3.0863
_cell_volume                     1012.9(5)
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_collection       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_molecular_graphics    ORTEP-III
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'RIGAKU/MSC Meacury CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6608
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.9684
_exptl_absorpt_correction_T_min  0.9000
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             478
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         3470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0302
_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)+(0.0497P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0826
_reflns_number_gt                2880
_reflns_number_total             3470
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol701741e-file003.cif
_cod_data_source_block           viologen
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1505543
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
N1 N 0.40930(16) 0.20240(10) 0.85974(10) 0.0149(3) Uani 1 1 d
C1 C 0.3555(2) 0.23365(14) 0.95448(13) 0.0225(4) Uani 1 1 d
H1 H 0.291(2) 0.1715(14) 0.9825(14) 0.029(5) Uiso 1 1 d
C2 C 0.3900(2) 0.34995(13) 1.01073(13) 0.0228(4) Uani 1 1 d
H2 H 0.345(3) 0.3663(15) 1.0726(15) 0.031(5) Uiso 1 1 d
C3 C 0.48315(19) 0.43664(12) 0.97130(12) 0.0151(3) Uani 1 1 d
C4 C 0.5419(2) 0.40057(13) 0.87551(13) 0.0203(3) Uani 1 1 d
H3 H 0.605(3) 0.4527(15) 0.8459(15) 0.032(5) Uiso 1 1 d
C5 C 0.5022(2) 0.28380(13) 0.82014(13) 0.0192(3) Uani 1 1 d
H4 H 0.539(2) 0.2552(14) 0.7551(15) 0.029(5) Uiso 1 1 d
C6 C 0.3677(2) 0.07483(12) 0.79800(14) 0.0181(3) Uani 1 1 d
H5 H 0.470(2) 0.0361(13) 0.8383(13) 0.022(4) Uiso 1 1 d
H6 H 0.376(2) 0.0768(13) 0.7180(14) 0.023(4) Uiso 1 1 d
C7 C 0.1792(2) 0.01779(12) 0.79700(12) 0.0160(3) Uani 1 1 d
C8 C 0.0227(2) 0.05031(13) 0.72642(13) 0.0172(3) Uani 1 1 d
H7 H 0.036(2) 0.1059(13) 0.6766(13) 0.018(4) Uiso 1 1 d
C9 C -0.1528(2) 0.00501(12) 0.73068(12) 0.0162(3) Uani 1 1 d
C10 C -0.1703(2) -0.07325(12) 0.80464(12) 0.0157(3) Uani 1 1 d
C11 C -0.0125(2) -0.10747(12) 0.87295(12) 0.0157(3) Uani 1 1 d
C12 C 0.1634(2) -0.06165(12) 0.86939(12) 0.0165(3) Uani 1 1 d
H8 H 0.271(2) -0.0839(13) 0.9145(13) 0.019(4) Uiso 1 1 d
O1 O -0.31435(14) 0.03314(9) 0.66718(9) 0.0214(3) Uani 1 1 d
C13 C -0.3011(2) 0.09991(15) 0.57899(14) 0.0224(4) Uani 1 1 d
H9 H -0.220(2) 0.1771(15) 0.6157(14) 0.025(4) Uiso 1 1 d
H10 H -0.249(2) 0.0529(14) 0.5224(15) 0.029(5) Uiso 1 1 d
H11 H -0.428(2) 0.1094(13) 0.5417(14) 0.025(4) Uiso 1 1 d
O2 O -0.34255(14) -0.11391(9) 0.81521(8) 0.0193(2) Uani 1 1 d
C14 C -0.4456(2) -0.21393(16) 0.72589(15) 0.0277(4) Uani 1 1 d
H12 H -0.371(3) -0.2820(15) 0.7282(15) 0.034(5) Uiso 1 1 d
H13 H -0.469(2) -0.1915(15) 0.6511(16) 0.034(5) Uiso 1 1 d
H14 H -0.559(3) -0.2366(14) 0.7452(14) 0.030(5) Uiso 1 1 d
O3 O -0.04592(14) -0.18505(8) 0.94059(9) 0.0195(2) Uani 1 1 d
C15 C 0.1100(2) -0.22865(15) 1.00743(14) 0.0219(4) Uani 1 1 d
H15 H 0.170(2) -0.2706(14) 0.9560(14) 0.029(5) Uiso 1 1 d
H16 H 0.200(2) -0.1629(14) 1.0653(14) 0.020(4) Uiso 1 1 d
H17 H 0.060(2) -0.2877(15) 1.0429(14) 0.023(4) Uiso 1 1 d
P1 P -0.00374(6) 0.46894(3) 0.75577(3) 0.01935(13) Uani 1 1 d
F1 F -0.12206(15) 0.57210(8) 0.77479(8) 0.0374(3) Uani 1 1 d
F2 F 0.11112(13) 0.36392(8) 0.73642(8) 0.0314(2) Uani 1 1 d
F3 F 0.05716(16) 0.47161(9) 0.89179(8) 0.0393(3) Uani 1 1 d
F4 F 0.17502(15) 0.56443(9) 0.77369(10) 0.0453(3) Uani 1 1 d
F5 F -0.18184(14) 0.37239(9) 0.73923(10) 0.0445(3) Uani 1 1 d
F6 F -0.06455(16) 0.46651(9) 0.62027(8) 0.0442(3) Uani 1 1 d
C16 C 0.2167(2) 0.26586(14) 0.51350(13) 0.0240(4) Uani 1 1 d
C17 C 0.3417(3) 0.38173(17) 0.53768(17) 0.0321(4) Uani 1 1 d
H18 H 0.333(3) 0.4115(16) 0.4707(18) 0.045(6) Uiso 1 1 d
H19 H 0.465(3) 0.3736(17) 0.5734(18) 0.052(6) Uiso 1 1 d
H20 H 0.304(3) 0.4374(18) 0.5853(19) 0.053(6) Uiso 1 1 d
C18 C 0.0232(3) 0.25590(17) 0.43535(15) 0.0274(4) Uani 1 1 d
H21 H -0.043(3) 0.3166(15) 0.4648(15) 0.035(5) Uiso 1 1 d
H22 H -0.047(3) 0.1813(17) 0.4247(15) 0.036(5) Uiso 1 1 d
H23 H 0.025(3) 0.2680(15) 0.3648(18) 0.039(5) Uiso 1 1 d
O4 O 0.27043(18) 0.18296(10) 0.55586(10) 0.0328(3) 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 0.0033 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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_3
C5 N1 C1 120.55(12) .
C5 N1 C6 119.46(12) .
C1 N1 C6 119.98(12) .
N1 C1 C2 120.64(14) .
N1 C1 H1 118.5(10) .
C2 C1 H1 120.9(10) .
C1 C2 C3 120.39(15) .
C1 C2 H2 116.6(11) .
C3 C2 H2 122.9(11) .
C2 C3 C4 117.35(14) .
C2 C3 C3 121.23(16) 2_667
C4 C3 C3 121.41(16) 2_667
C5 C4 C3 120.70(14) .
C5 C4 H3 117.5(11) .
C3 C4 H3 121.8(11) .
N1 C5 C4 120.31(14) .
N1 C5 H4 115.8(10) .
C4 C5 H4 123.9(10) .
C7 C6 N1 110.38(12) .
C7 C6 H5 113.3(9) .
N1 C6 H5 106.8(9) .
C7 C6 H6 112.6(9) .
N1 C6 H6 105.4(9) .
H5 C6 H6 107.9(13) .
C8 C7 C12 121.14(14) .
C8 C7 C6 118.52(13) .
C12 C7 C6 120.28(13) .
C7 C8 C9 119.37(14) .
C7 C8 H7 120.2(9) .
C9 C8 H7 120.4(9) .
O1 C9 C8 124.06(13) .
O1 C9 C10 115.90(13) .
C8 C9 C10 120.03(13) .
O2 C10 C11 118.98(12) .
O2 C10 C9 120.92(13) .
C11 C10 C9 120.04(13) .
O3 C11 C10 115.09(13) .
O3 C11 C12 124.90(13) .
C10 C11 C12 120.02(13) .
C7 C12 C11 119.38(14) .
C7 C12 H8 119.3(9) .
C11 C12 H8 121.3(9) .
C9 O1 C13 116.36(12) .
O1 C13 H9 109.5(9) .
O1 C13 H10 108.6(9) .
H9 C13 H10 111.0(13) .
O1 C13 H11 104.9(9) .
H9 C13 H11 111.4(13) .
H10 C13 H11 111.3(13) .
C10 O2 C14 113.16(12) .
O2 C14 H12 109.7(10) .
O2 C14 H13 109.3(10) .
H12 C14 H13 109.7(14) .
O2 C14 H14 105.3(10) .
H12 C14 H14 109.9(14) .
H13 C14 H14 112.9(15) .
C11 O3 C15 117.52(12) .
O3 C15 H15 110.3(10) .
O3 C15 H16 110.7(9) .
H15 C15 H16 110.9(13) .
O3 C15 H17 106.3(10) .
H15 C15 H17 105.6(13) .
H16 C15 H17 112.8(13) .
F6 P1 F3 179.89(6) .
F6 P1 F4 90.30(6) .
F3 P1 F4 89.67(6) .
F6 P1 F5 90.36(6) .
F3 P1 F5 89.66(6) .
F4 P1 F5 179.24(7) .
F6 P1 F2 89.55(6) .
F3 P1 F2 90.56(6) .
F4 P1 F2 90.43(6) .
F5 P1 F2 89.21(6) .
F6 P1 F1 90.45(6) .
F3 P1 F1 89.44(6) .
F4 P1 F1 90.67(6) .
F5 P1 F1 89.69(6) .
F2 P1 F1 178.89(6) .
O4 C16 C17 121.38(16) .
O4 C16 C18 121.54(15) .
C17 C16 C18 117.08(15) .
C16 C17 H18 111.7(12) .
C16 C17 H19 110.0(12) .
H18 C17 H19 110.2(18) .
C16 C17 H20 109.3(13) .
H18 C17 H20 105.0(17) .
H19 C17 H20 110.5(17) .
C16 C18 H21 111.9(10) .
C16 C18 H22 112.3(11) .
H21 C18 H22 108.7(15) .
C16 C18 H23 110.5(13) .
H21 C18 H23 106.0(15) .
H22 C18 H23 107.2(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.3457(19) .
N1 C1 1.347(2) .
N1 C6 1.5102(19) .
C1 C2 1.378(2) .
C1 H1 0.985(17) .
C2 C3 1.389(2) .
C2 H2 0.918(19) .
C3 C4 1.391(2) .
C3 C3 1.490(3) 2_667
C4 C5 1.378(2) .
C4 H3 0.908(18) .
C5 H4 0.940(18) .
C6 C7 1.506(2) .
C6 H5 0.995(16) .
C6 H6 1.003(16) .
C7 C8 1.392(2) .
C7 C12 1.393(2) .
C8 C9 1.397(2) .
C8 H7 0.970(15) .
C9 O1 1.3637(17) .
C9 C10 1.400(2) .
C10 O2 1.3894(17) .
C10 C11 1.397(2) .
C11 O3 1.3644(17) .
C11 C12 1.398(2) .
C12 H8 0.942(16) .
O1 C13 1.4430(19) .
C13 H9 0.988(17) .
C13 H10 1.011(18) .
C13 H11 0.973(18) .
O2 C14 1.441(2) .
C14 H12 1.028(19) .
C14 H13 0.965(19) .
C14 H14 0.978(18) .
O3 C15 1.4346(18) .
C15 H15 0.982(19) .
C15 H16 0.997(17) .
C15 H17 0.964(17) .
P1 F6 1.5869(11) .
P1 F3 1.5925(11) .
P1 F4 1.5940(11) .
P1 F5 1.6012(11) .
P1 F2 1.6075(10) .
P1 F1 1.6076(11) .
C16 O4 1.2218(19) .
C16 C17 1.494(2) .
C16 C18 1.495(2) .
C17 H18 0.93(2) .
C17 H19 0.94(2) .
C17 H20 0.93(2) .
C18 H21 0.99(2) .
C18 H22 0.935(19) .
C18 H23 0.90(2) .
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_1
_geom_torsion_site_symmetry_4
C5 N1 C1 C2 1.8(2) . .
C6 N1 C1 C2 -179.05(14) . .
N1 C1 C2 C3 -0.8(3) . .
C1 C2 C3 C4 -1.2(2) . .
C1 C2 C3 C3 178.13(17) . 2_667
C2 C3 C4 C5 2.4(2) . .
C3 C3 C4 C5 -176.99(16) 2_667 .
C1 N1 C5 C4 -0.6(2) . .
C6 N1 C5 C4 -179.81(13) . .
C3 C4 C5 N1 -1.5(2) . .
C5 N1 C6 C7 -142.91(14) . .
C1 N1 C6 C7 37.91(18) . .
N1 C6 C7 C8 71.33(17) . .
N1 C6 C7 C12 -105.79(15) . .
C12 C7 C8 C9 1.8(2) . .
C6 C7 C8 C9 -175.31(12) . .
C7 C8 C9 O1 178.52(13) . .
C7 C8 C9 C10 -0.6(2) . .
O1 C9 C10 O2 -2.98(19) . .
C8 C9 C10 O2 176.21(12) . .
O1 C9 C10 C11 179.84(12) . .
C8 C9 C10 C11 -1.0(2) . .
O2 C10 C11 O3 3.56(18) . .
C9 C10 C11 O3 -179.22(12) . .
O2 C10 C11 C12 -175.85(12) . .
C9 C10 C11 C12 1.4(2) . .
C8 C7 C12 C11 -1.4(2) . .
C6 C7 C12 C11 175.68(12) . .
O3 C11 C12 C7 -179.57(12) . .
C10 C11 C12 C7 -0.2(2) . .
C8 C9 O1 C13 9.4(2) . .
C10 C9 O1 C13 -171.48(13) . .
C11 C10 O2 C14 -98.86(16) . .
C9 C10 O2 C14 83.94(17) . .
C10 C11 O3 C15 176.42(13) . .
C12 C11 O3 C15 -4.2(2) . .
