#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/22/8102205.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_8102205
loop_
_publ_author_name
'Thomas Ziegler'
'Moritz Uhde'
'Marius Kirchmann'
_publ_section_title
;
 Crystal structure nonafluorobutane-1-sulfonic acid
 2-(4-(4-diethyliminium-but-2-enylidene)-4H-pyridazin-1-yl)phenylimide,
 C22H21F9N4O2S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              31
_journal_volume                  223
_journal_year                    2008
_chemical_formula_moiety         'C22 H21 F9 N4 O2 S'
_chemical_formula_sum            'C22 H21 F9 N4 O2 S'
_chemical_formula_weight         576.49
_chemical_name_systematic
;
nonafluorobutane-1-sulfonic acid 
(2-(4-(4-diethyliminium-but-2-enylidene)-4H-pyridazin-1-yl)phenylimide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.459(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.4814(19)
_cell_length_b                   11.4911(10)
_cell_length_c                   14.4548(19)
_cell_measurement_temperature    173(2)
_cell_volume                     2439.2(5)
_computing_cell_refinement       'Stoe X-Area'
_computing_data_collection       'Stoe X-Area'
_computing_data_reduction        'Stoe X-Area'
_computing_molecular_graphics    'ORTEP 3'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1331
_diffrn_reflns_av_sigmaI/netI    0.0715
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27378
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         5.67
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.211
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0944
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+6.2134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1438
_reflns_number_gt                3267
_reflns_number_total             4575
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2132.cff
_cod_data_source_block           ziegler_die_wievielte
_cod_original_sg_symbol_H-M      P12(1)/c1
_cod_database_code               8102205
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_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.29463(8) -0.48463(10) 0.25806(8) 0.0279(3) Uani 1 4 e d . . .
F11 F 0.17565(19) -0.3874(3) 0.3316(2) 0.0451(8) Uani 1 4 e d . . .
F12 F 0.15708(18) -0.3426(2) 0.1800(2) 0.0437(7) Uani 1 4 e d . . .
F21 F 0.12842(19) -0.6222(3) 0.2591(2) 0.0471(8) Uani 1 4 e d . . .
F22 F 0.08567(19) -0.5423(3) 0.11476(19) 0.0459(8) Uani 1 4 e d . . .
F31 F 0.0139(2) -0.5029(4) 0.3169(2) 0.0750(12) Uani 1 4 e d . . .
F32 F -0.0105(2) -0.3775(3) 0.2008(3) 0.0636(10) Uani 1 4 e d . . .
F41 F -0.0951(2) -0.5319(4) 0.0698(2) 0.0866(14) Uani 1 4 e d . . .
F42 F -0.0555(3) -0.6726(4) 0.1697(4) 0.0961(15) Uani 1 4 e d . . .
F43 F -0.1450(2) -0.5408(4) 0.1893(3) 0.0821(13) Uani 1 4 e d . . .
O11 O 0.3216(2) -0.5357(3) 0.3539(2) 0.0356(8) Uani 1 4 e d . . .
O12 O 0.2790(2) -0.5641(3) 0.1773(2) 0.0353(8) Uani 1 4 e d . . .
N1 N 0.7704(3) -0.1249(4) 0.9073(3) 0.0342(10) Uani 1 4 e d . . .
N2 N 0.3516(2) -0.3756(3) 0.2567(3) 0.0281(9) Uani 1 4 e d . . .
N3 N 0.4884(2) -0.2158(3) 0.2785(3) 0.0254(8) Uani 1 4 e d . . .
N4 N 0.4914(3) -0.0994(3) 0.2976(3) 0.0307(9) Uani 1 4 e d . . .
C1 C 0.1772(3) -0.4306(4) 0.2446(3) 0.0303(11) Uani 1 4 e d . . .
C2 C 0.1008(3) -0.5224(4) 0.2101(3) 0.0314(11) Uani 1 4 e d . . .
C3 C 0.0087(3) -0.4892(5) 0.2234(4) 0.0400(12) Uani 1 4 e d . . .
C4 C -0.0728(4) -0.5618(6) 0.1617(4) 0.0517(15) Uani 1 4 e d . . .
C5 C 0.4314(3) -0.2468(4) 0.1820(3) 0.0270(10) Uani 1 4 e d . . .
C6 C 0.3612(3) -0.3272(4) 0.1709(3) 0.0279(10) Uani 1 4 e d . . .
C7 C 0.3051(3) -0.3489(4) 0.0747(3) 0.0335(11) Uani 1 4 e d . . .
H7 H 0.2577 -0.4022 0.0633 0.040 Uiso 1 4 e calc R . .
C8 C 0.3203(3) -0.2907(5) -0.0033(3) 0.0363(12) Uani 1 4 e d . . .
H8 H 0.2823 -0.3057 -0.0662 0.044 Uiso 1 4 e calc R . .
C9 C 0.3900(3) -0.2115(5) 0.0102(4) 0.0381(12) Uani 1 4 e d . . .
H9 H 0.3988 -0.1735 -0.0429 0.046 Uiso 1 4 e calc R . .
C10 C 0.4465(3) -0.1893(4) 0.1035(3) 0.0331(11) Uani 1 4 e d . . .
H10 H 0.4942 -0.1366 0.1140 0.040 Uiso 1 4 e calc R . .
C13 C 0.5373(3) -0.0682(4) 0.3857(3) 0.0314(11) Uani 1 4 e d . . .
H13 H 0.5408 0.0112 0.3987 0.038 Uiso 1 4 e calc R . .
C14 C 0.5830(3) -0.1433(4) 0.4648(3) 0.0272(10) Uani 1 4 e d . . .
C15 C 0.5800(3) -0.2624(4) 0.4389(3) 0.0264(10) Uani 1 4 e d . . .
H15 H 0.6100 -0.3179 0.4847 0.032 Uiso 1 4 e calc R . .
C16 C 0.5325(3) -0.2946(4) 0.3457(3) 0.0271(10) Uani 1 4 e d . . .
H16 H 0.5306 -0.3727 0.3283 0.033 Uiso 1 4 e calc R . .
C17 C 0.6230(3) -0.0933(5) 0.5567(3) 0.0334(11) Uani 1 4 e d . . .
H17 H 0.6214 -0.0126 0.5601 0.040 Uiso 1 4 e calc R . .
C18 C 0.6645(3) -0.1513(4) 0.6425(3) 0.0312(11) Uani 1 4 e d . . .
H18 H 0.6719 -0.2314 0.6397 0.037 Uiso 1 4 e calc R . .
C19 C 0.6961(3) -0.0977(4) 0.7334(3) 0.0336(11) Uani 1 4 e d . . .
H19 H 0.6876 -0.0182 0.7387 0.040 Uiso 1 4 e calc R . .
C20 C 0.7402(3) -0.1616(4) 0.8157(3) 0.0313(11) Uani 1 4 e d . . .
H20 H 0.7499 -0.2398 0.8057 0.038 Uiso 1 4 e calc R . .
C21 C 0.7572(4) -0.0037(5) 0.9338(4) 0.0424(13) Uani 1 4 e d . . .
H21A H 0.7528 -0.0028 0.9993 0.051 Uiso 1 4 e calc R . .
H21B H 0.6998 0.0246 0.8899 0.051 Uiso 1 4 e calc R . .
C22 C 0.8319(4) 0.0783(5) 0.9299(5) 0.0571(16) Uani 1 4 e d . . .
H22A H 0.8886 0.0536 0.9758 0.086 Uiso 1 4 e calc R . .
H22B H 0.8178 0.1556 0.9461 0.086 Uiso 1 4 e calc R . .
H22C H 0.8369 0.0782 0.8654 0.086 Uiso 1 4 e calc R . .
C23 C 0.8227(4) -0.2048(5) 0.9830(4) 0.0476(14) Uani 1 4 e d . . .
H23A H 0.8005 -0.2834 0.9660 0.057 Uiso 1 4 e calc R . .
H23B H 0.8134 -0.1848 1.0443 0.057 Uiso 1 4 e calc R . .
C24 C 0.9230(4) -0.2009(6) 0.9957(5) 0.0638(18) Uani 1 4 e d . . .
H24A H 0.9541 -0.2586 1.0423 0.096 Uiso 1 4 e calc R . .
H24B H 0.9466 -0.1252 1.0185 0.096 Uiso 1 4 e calc R . .
H24C H 0.9324 -0.2163 0.9342 0.096 Uiso 1 4 e 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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S1 O12 116.4(2) . . ?
O11 S1 N2 110.6(2) . . ?
O12 S1 N2 117.2(2) . . ?
O11 S1 C1 102.3(2) . . ?
O12 S1 C1 102.5(2) . . ?
N2 S1 C1 105.7(2) . . ?
C20 N1 C23 119.0(4) . . ?
C20 N1 C21 121.7(4) . . ?
C23 N1 C21 119.3(4) . . ?
C6 N2 S1 123.6(3) . . ?
C16 N3 N4 122.5(4) . . ?
C16 N3 C5 123.3(4) . . ?
N4 N3 C5 114.2(3) . . ?
C13 N4 N3 116.3(4) . . ?
F12 C1 F11 107.4(4) . . ?
F12 C1 C2 107.7(4) . . ?
F11 C1 C2 108.1(4) . . ?
F12 C1 S1 109.1(3) . . ?
F11 C1 S1 109.0(3) . . ?
C2 C1 S1 115.2(3) . . ?
F22 C2 F21 108.5(4) . . ?
F22 C2 C3 107.5(4) . . ?
F21 C2 C3 107.3(4) . . ?
F22 C2 C1 108.3(4) . . ?
F21 C2 C1 109.2(4) . . ?
C3 C2 C1 115.7(4) . . ?
F32 C3 F31 107.3(5) . . ?
F32 C3 C4 107.5(4) . . ?
F31 C3 C4 107.2(4) . . ?
F32 C3 C2 110.5(4) . . ?
F31 C3 C2 109.5(4) . . ?
C4 C3 C2 114.4(4) . . ?
F42 C4 F41 109.2(6) . . ?
F42 C4 F43 108.8(5) . . ?
F41 C4 F43 106.3(5) . . ?
F42 C4 C3 111.9(5) . . ?
F41 C4 C3 110.5(5) . . ?
F43 C4 C3 110.0(5) . . ?
C10 C5 C6 123.0(4) . . ?
C10 C5 N3 117.5(4) . . ?
C6 C5 N3 119.5(4) . . ?
C5 C6 C7 116.5(4) . . ?
C5 C6 N2 117.0(4) . . ?
C7 C6 N2 126.5(4) . . ?
C8 C7 C6 120.2(5) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 121.9(4) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 119.1(5) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C5 119.3(5) . . ?
C9 C10 H10 120.3 . . ?
C5 C10 H10 120.3 . . ?
N4 C13 C14 126.7(5) . . ?
N4 C13 H13 116.6 . . ?
C14 C13 H13 116.6 . . ?
C17 C14 C15 128.0(4) . . ?
C17 C14 C13 118.1(4) . . ?
C15 C14 C13 113.9(4) . . ?
C16 C15 C14 119.0(4) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
N3 C16 C15 121.4(4) . . ?
N3 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C14 126.7(5) . . ?
C18 C17 H17 116.6 . . ?
C14 C17 H17 116.6 . . ?
C17 C18 C19 124.2(5) . . ?
C17 C18 H18 117.9 . . ?
C19 C18 H18 117.9 . . ?
C20 C19 C18 120.5(5) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
N1 C20 C19 127.8(5) . . ?
N1 C20 H20 116.1 . . ?
C19 C20 H20 116.1 . . ?
N1 C21 C22 114.2(4) . . ?
N1 C21 H21A 108.7 . . ?
C22 C21 H21A 108.7 . . ?
N1 C21 H21B 108.7 . . ?
C22 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C23 C24 112.2(5) . . ?
N1 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
N1 C23 H23B 109.2 . . ?
C24 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
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
S1 O11 1.439(3) . ?
S1 O12 1.440(3) . ?
S1 N2 1.536(4) . ?
S1 C1 1.871(5) . ?
F11 C1 1.360(5) . ?
F12 C1 1.343(5) . ?
F21 C2 1.345(5) . ?
F22 C2 1.343(5) . ?
F31 C3 1.338(5) . ?
F32 C3 1.335(6) . ?
F41 C4 1.309(6) . ?
F42 C4 1.299(7) . ?
F43 C4 1.324(6) . ?
N1 C20 1.326(6) . ?
N1 C23 1.460(6) . ?
N1 C21 1.476(6) . ?
N2 C6 1.410(5) . ?
N3 C16 1.346(6) . ?
N3 N4 1.363(5) . ?
N3 C5 1.439(5) . ?
N4 C13 1.298(6) . ?
C1 C2 1.545(7) . ?
C2 C3 1.545(6) . ?
C3 C4 1.540(8) . ?
C5 C10 1.395(6) . ?
C5 C6 1.396(6) . ?
C6 C7 1.409(6) . ?
C7 C8 1.394(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C13 C14 1.429(6) . ?
C13 H13 0.9300 . ?
C14 C17 1.398(6) . ?
C14 C15 1.416(6) . ?
C15 C16 1.366(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.375(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.392(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.507(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.505(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653924
