#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/90/2239097.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_2239097
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Kobkeatthawin, Thawanrat'
'Ruanwas, Pumsak'
'Quah, Ching Kheng'
'Chantrapromma, Suchada'
_publ_section_title
;
 2-[(<i>E</i>)-2-(4-Ethoxyphenyl)ethenyl]-1-methylquinolinium
 4-fluorobenzenesulfonate
;
_journal_coeditor_code           RZ5097
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o11
_journal_page_last               o12
_journal_paper_doi               10.1107/S1600536813032509
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C20 H20 N O +, C6 H4 F O3 S -'
_chemical_formula_moiety         'C20 H20 N O +, C6 H4 F O3 S -'
_chemical_formula_sum            'C26 H24 F N O4 S'
_chemical_formula_weight         465.52
_chemical_name_systematic
;
2-[(<i>E</i>)-2-(4-Ethoxyphenyl)ethenyl]-1-methylquinolinium
4-fluorobenzenesulfonate
;
_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                 95.102(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4366(3)
_cell_length_b                   9.8909(5)
_cell_length_c                   34.3628(15)
_cell_measurement_reflns_used    4993
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.14
_cell_volume                     2179.00(18)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), Mercury (Macrae
<i>et al.</i>,
2006) and publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            19050
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.14
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.493
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         4993
_refine_ls_number_restraints     418
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0388P)^2^+4.3613P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1538
_reflns_number_gt                3609
_reflns_number_total             4993
_reflns_threshold_expression     I>2\s(I)
_iucr_refine_instructions_details
;
TITL tk1fb_0m in P2(1)/n   (100K)
CELL 0.71073   6.4366   9.8909  34.3628  90.000  95.102  90.000
ZERR    4.00   0.0003   0.0005   0.0015   0.000   0.002   0.000
LATT  1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C H N O F S
UNIT 104 96 4 16 4 4
SIZE 0.046 0.117 0.371
L.S. 10
BOND $H
FMAP 2 1 60
PLAN 20
OMIT -4 55
ACTA
CONF
WGHT    0.038800    4.361300
FVAR       0.28949   0.61035
N1    3    1.559311    0.123532    0.183105    11.00000    0.01397    0.01302 =
         0.02473   -0.00016    0.00088   -0.00009
C1    1    1.748810    0.085664    0.203817    11.00000    0.01086    0.02211 =
         0.01813   -0.00020    0.00165    0.00021
C2    1    1.892248    0.182772    0.220240    11.00000    0.02064    0.01508 =
         0.02784   -0.00238    0.00309    0.00083
AFIX  43
H2A   2    1.865488    0.274764    0.217260    11.00000   -1.20000
AFIX   0
C3    1    2.073322    0.137492    0.240845    11.00000    0.01743    0.02555 =
         0.02676   -0.00690    0.00084   -0.01008
AFIX  43
H3A   2    2.166033    0.200822    0.252439    11.00000   -1.20000
AFIX   0
C4    1    2.122258    0.000592    0.244910    11.00000    0.01589    0.02683 =
         0.02091    0.00172   -0.00110    0.00143
AFIX  43
H4A   2    2.246033   -0.026677    0.258701    11.00000   -1.20000
AFIX   0
C5    1    1.985387   -0.092792    0.228299    11.00000    0.02135    0.01704 =
         0.02306    0.00114    0.00134    0.00333
AFIX  43
H5A   2    2.018182   -0.184234    0.230347    11.00000   -1.20000
AFIX   0
C6    1    1.795661   -0.052775    0.208149    11.00000    0.01536    0.01963 =
         0.02009   -0.00267    0.00065   -0.00226
C7    1    1.649228   -0.148893    0.192549    11.00000    0.01928    0.01321 =
         0.02495   -0.00137    0.00308   -0.00044
AFIX  43
H7A   2    1.678996   -0.240609    0.195211    11.00000   -1.20000
AFIX   0
C8    1    1.466328   -0.109039    0.173796    11.00000    0.01672    0.01666 =
         0.02610   -0.00186    0.00186   -0.00563
AFIX  43
H8A   2    1.369846   -0.173767    0.164357    11.00000   -1.20000
AFIX   0
C9    1    1.419075    0.030040    0.168269    11.00000    0.01000    0.02092 =
         0.01837   -0.00234    0.00264   -0.00136
C10   1    1.224733    0.074477    0.147146    11.00000    0.01443    0.02056 =
         0.02415   -0.00118    0.00198    0.00096
PART 1
AFIX   3
H10A  2    1.195854    0.169337    0.144226    21.00000   -1.20000
AFIX   3
PART 2
H10B  2    1.197084    0.169867    0.146636   -21.00000   -1.20000
AFIX   0
PART 0
C20   1    1.511954    0.268055    0.177005    11.00000    0.01977    0.01517 =
         0.03705    0.00163   -0.00516    0.00089
AFIX 137
H20A  2    1.491205    0.286483    0.149505    11.00000   -1.50000
H20B  2    1.626186    0.321345    0.188446    11.00000   -1.50000
H20C  2    1.387600    0.290545    0.189086    11.00000   -1.50000
AFIX   0
SIMU 0.01 O1A > C19B
ISOR 0.01 O1A > C19B
PART   1
O1A   4    0.328101    0.097218    0.042352    21.00000    0.01919    0.06505 =
         0.02973    0.00489   -0.00853    0.01003
C11A  1    1.085978   -0.013928    0.131770    21.00000    0.01292    0.01944 =
         0.01794    0.00271   -0.00078    0.00456
AFIX  43
H11A  2    1.115563   -0.105254    0.135579    21.00000   -1.20000
AFIX   0
C12A  1    0.889245    0.021445    0.109196    21.00000    0.01256    0.02404 =
         0.01540    0.00376    0.00046    0.00642
C13A  1    0.767495   -0.081533    0.091481    21.00000    0.01786    0.02587 =
         0.02557    0.00518   -0.00554    0.00282
AFIX  43
H13A  2    0.810514   -0.170795    0.095012    21.00000   -1.20000
AFIX   0
C14A  1    0.583449   -0.054177    0.068675    21.00000    0.01868    0.02652 =
         0.02896   -0.00183   -0.00318    0.00373
AFIX  43
H14A  2    0.506752   -0.124435    0.056500    21.00000   -1.20000
AFIX   0
C15A  1    0.514622    0.076976    0.064103    21.00000    0.01581    0.03531 =
         0.02187    0.00290   -0.00283    0.00630
C16A  1    0.627695    0.181958    0.082930    21.00000    0.01863    0.02577 =
         0.02996    0.00840    0.00535    0.01011
AFIX  43
H16A  2    0.578895    0.270330    0.080521    21.00000   -1.20000
AFIX   0
C17A  1    0.814051    0.154334    0.105379    21.00000    0.01390    0.02534 =
         0.01826    0.00325    0.00433    0.00022
AFIX  43
H17A  2    0.889108    0.224576    0.117925    21.00000   -1.20000
AFIX   0
C18A  1    0.252013    0.237551    0.037913    21.00000    0.02919    0.07738 =
         0.03024    0.00897   -0.00227    0.03505
AFIX  23
H18A  2    0.355553    0.293258    0.026731    21.00000   -1.20000
H18B  2    0.227115    0.274540    0.063225    21.00000   -1.20000
AFIX   0
C19A  1    0.054243    0.237117    0.011714    21.00000    0.03695    0.10978 =
         0.03590    0.00481   -0.00634    0.03347
AFIX 137
H19A  2   -0.005347    0.326158    0.010835    21.00000   -1.50000
H19B  2   -0.042313    0.174525    0.021568    21.00000   -1.50000
H19C  2    0.083168    0.210387   -0.014113    21.00000   -1.50000
AFIX   0
PART   2
SAME O1A > C19A
O1B   4    0.334269    0.153020    0.040723   -21.00000    0.02129    0.02317 =
         0.02568    0.00283   -0.00570   -0.00787
C11B  1    1.076332   -0.005361    0.127034   -21.00000    0.01818    0.02194 =
         0.01671    0.00163    0.00023   -0.00435
AFIX  43
H11B  2    1.101335   -0.097976    0.127212   -21.00000   -1.20000
AFIX   0
C12B  1    0.883322    0.040833    0.105418   -21.00000    0.01063    0.02715 =
         0.01863    0.00321    0.00056   -0.00029
C13B  1    0.748196   -0.059514    0.087968   -21.00000    0.02117    0.01838 =
         0.02527    0.00290   -0.00098    0.00320
AFIX  43
H13B  2    0.784179   -0.150393    0.090338   -21.00000   -1.20000
AFIX   0
C14B  1    0.560523   -0.021543    0.067164   -21.00000    0.01850    0.02536 =
         0.02146    0.00061   -0.00750   -0.00193
AFIX  43
H14B  2    0.469197   -0.087245    0.056450   -21.00000   -1.20000
AFIX   0
C15B  1    0.512013    0.111653    0.062651   -21.00000    0.01527    0.02166 =
         0.01946    0.00435    0.00201    0.00609
C16B  1    0.646502    0.210769    0.078328   -21.00000    0.01519    0.01891 =
         0.02567    0.00504    0.00465   -0.00095
AFIX  43
H16B  2    0.612476    0.301559    0.074722   -21.00000   -1.20000
AFIX   0
C17B  1    0.830563    0.174888    0.099252   -21.00000    0.01269    0.01453 =
         0.02341    0.00781    0.00406   -0.00106
AFIX  43
H17B  2    0.920855    0.242071    0.109401   -21.00000   -1.20000
AFIX   0
C18B  1    0.188575    0.056804    0.023651   -21.00000    0.03089    0.04638 =
         0.03642    0.00235   -0.00157   -0.00704
AFIX  23
H18C  2    0.137921   -0.000769    0.043614   -21.00000   -1.20000
H18D  2    0.253015    0.000488    0.004988   -21.00000   -1.20000
AFIX   0
C19B  1    0.012479    0.137987    0.003525   -21.00000    0.01658    0.05726 =
         0.03911    0.01289   -0.00685    0.00584
AFIX 137
H19D  2   -0.092676    0.077828   -0.008011   -21.00000   -1.50000
H19E  2    0.064679    0.192854   -0.016491   -21.00000   -1.50000
H19F  2   -0.046810    0.195026    0.022250   -21.00000   -1.50000
AFIX   0
PART   0
S1    6    0.975680    0.534460    0.164034    11.00000    0.01260    0.01534 =
         0.03285   -0.00428   -0.00396    0.00079
F1    5    0.350837    0.611626    0.030195    11.00000    0.04001    0.09645 =
         0.04056   -0.01902   -0.02218    0.01801
O2    4    0.864804    0.524250    0.198990    11.00000    0.02166    0.02693 =
         0.02985    0.00347    0.00149   -0.00141
O3    4    1.093074    0.413884    0.156282    11.00000    0.01954    0.02321 =
         0.05592   -0.01290   -0.01046    0.00703
O4    4    1.096943    0.658436    0.162535    11.00000    0.01931    0.02249 =
         0.03549   -0.00398   -0.00314   -0.00564
C21   1    0.781200    0.548438    0.123720    11.00000    0.01448    0.01599 =
         0.03525   -0.00682   -0.00502   -0.00312
C22   1    0.839346    0.536129    0.085954    11.00000    0.01634    0.04934 =
         0.03314   -0.01839   -0.00048    0.00270
AFIX  43
H22A  2    0.976314    0.514113    0.081967    11.00000   -1.20000
AFIX   0
C23   1    0.694548    0.556438    0.054081    11.00000    0.03132    0.06735 =
         0.03150   -0.02102   -0.00080    0.00286
AFIX  43
H23A  2    0.732047    0.548830    0.028653    11.00000   -1.20000
AFIX   0
C24   1    0.493048    0.588306    0.061442    11.00000    0.02890    0.04848 =
         0.03299   -0.01176   -0.01458    0.00456
C25   1    0.429859    0.598393    0.098328    11.00000    0.01390    0.02771 =
         0.04282   -0.00660   -0.00544    0.00149
AFIX  43
H25A  2    0.292169    0.619120    0.102114    11.00000   -1.20000
AFIX   0
C26   1    0.575471    0.577056    0.129893    11.00000    0.01715    0.01514 =
         0.03106   -0.00292    0.00115   -0.00140
AFIX  43
H26A  2    0.535488    0.581891    0.155205    11.00000   -1.20000
HKLF 4
REM  tk1fb_0m in P2(1)/n   (100K)
REM R1 =  0.0649 for   3609 Fo > 4sig(Fo)  and  0.0959 for all   4993 data
REM    392 parameters refined using    418 restraints
END
WGHT      0.0388      4.3614
REM Highest difference peak  0.390,  deepest hole -0.493,  1-sigma level  0.073
Q1    1   1.0249  0.4560  0.1578  11.00000  0.05    0.39
Q2    1   1.1083  0.5813  0.1585  11.00000  0.05    0.36
Q3    1   0.9666  0.5243  0.1368  11.00000  0.05    0.35
Q4    1   1.0023  0.6287  0.1594  11.00000  0.05    0.33
Q5    1   0.8937  0.0926  0.1005  11.00000  0.05    0.32
Q6    1   0.2686  0.2942  0.0422  11.00000  0.05    0.31
Q7    1   1.8487  0.1324  0.2011  11.00000  0.05    0.31
Q8    1   0.3390  0.0284  0.0394  11.00000  0.05    0.30
Q9    1   1.7879  0.0170  0.2021  11.00000  0.05    0.29
Q10   1   1.0831  0.6799  0.1397  11.00000  0.05    0.29
Q11   1   0.2124  0.1765  0.0445  11.00000  0.05    0.28
Q12   1   1.0806  0.7653  0.1612  11.00000  0.05    0.26
Q13   1   1.4948 -0.1367  0.1987  11.00000  0.05    0.26
Q14   1   0.3021  0.5410  0.0395  11.00000  0.05    0.25
Q15   1   0.9837  0.5336  0.2097  11.00000  0.05    0.25
Q16   1   0.8103  0.5783  0.1021  11.00000  0.05    0.25
Q17   1   0.4701  0.6314  0.0810  11.00000  0.05    0.24
Q18   1   1.9834 -0.2132  0.2236  11.00000  0.05    0.24
Q19   1   0.9984  0.3460  0.1580  11.00000  0.05    0.23
Q20   1   1.4988  0.1906  0.1788  11.00000  0.05    0.23
;
_cod_data_source_file            rz5097sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2239097
_cod_database_fobs_code          2239097
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 1.5593(3) 0.1235(2) 0.18311(7) 0.0173(5) Uani d . 1 1 . .
C C1 1.7488(4) 0.0857(3) 0.20382(8) 0.0170(6) Uani d . 1 1 . .
C C2 1.8922(4) 0.1828(3) 0.22024(9) 0.0211(6) Uani d . 1 1 . .
H H2A 1.8655 0.2748 0.2173 0.025 Uiso calc R 1 1 . .
C C3 2.0733(4) 0.1375(3) 0.24085(9) 0.0233(6) Uani d . 1 1 . .
H H3A 2.1660 0.2008 0.2524 0.028 Uiso calc R 1 1 . .
C C4 2.1223(4) 0.0006(3) 0.24491(9) 0.0214(6) Uani d . 1 1 . .
H H4A 2.2460 -0.0267 0.2587 0.026 Uiso calc R 1 1 . .
C C5 1.9854(4) -0.0928(3) 0.22830(9) 0.0205(6) Uani d . 1 1 . .
H H5A 2.0182 -0.1842 0.2303 0.025 Uiso calc R 1 1 . .
C C6 1.7957(4) -0.0528(3) 0.20815(8) 0.0184(6) Uani d . 1 1 . .
C C7 1.6492(4) -0.1489(3) 0.19255(9) 0.0191(6) Uani d . 1 1 . .
H H7A 1.6790 -0.2406 0.1952 0.023 Uiso calc R 1 1 . .
C C8 1.4663(4) -0.1090(3) 0.17380(9) 0.0198(6) Uani d . 1 1 . .
H H8A 1.3698 -0.1738 0.1644 0.024 Uiso calc R 1 1 . .
C C9 1.4191(4) 0.0300(3) 0.16827(8) 0.0163(5) Uani d . 1 1 A .
C C10 1.2247(4) 0.0745(3) 0.14715(9) 0.0197(6) Uani d . 1 1 . .
H H10A 1.1959 0.1693 0.1442 0.024 Uiso d PR 0.610(6) 1 A 1
H H10B 1.1971 0.1699 0.1466 0.024 Uiso d PR 0.390(6) 1 A 2
C C20 1.5120(5) 0.2681(3) 0.17700(10) 0.0245(7) Uani d . 1 1 . .
H H20A 1.4912 0.2865 0.1495 0.037 Uiso calc R 1 1 . .
H H20B 1.6262 0.3213 0.1884 0.037 Uiso calc R 1 1 . .
H H20C 1.3876 0.2905 0.1891 0.037 Uiso calc R 1 1 . .
O O1A 0.3281(9) 0.0972(6) 0.04235(19) 0.0386(14) Uani d PDU 0.610(6) 1 A 1
C C11A 1.086(2) -0.0139(19) 0.1318(6) 0.0169(19) Uani d PDU 0.610(6) 1 A 1
H H11A 1.1156 -0.1053 0.1356 0.020 Uiso calc PR 0.610(6) 1 A 1
C C12A 0.889(2) 0.0214(10) 0.1092(4) 0.0174(16) Uani d PDU 0.610(6) 1 A 1
C C13A 0.7675(19) -0.0815(10) 0.0915(5) 0.0235(16) Uani d PDU 0.610(6) 1 A 1
H H13A 0.8105 -0.1708 0.0950 0.028 Uiso calc PR 0.610(6) 1 A 1
C C14A 0.5834(16) -0.0542(8) 0.0687(4) 0.0250(16) Uani d PDU 0.610(6) 1 A 1
H H14A 0.5068 -0.1244 0.0565 0.030 Uiso calc PR 0.610(6) 1 A 1
C C15A 0.5146(15) 0.0770(8) 0.0641(4) 0.0246(16) Uani d PDU 0.610(6) 1 A 1
C C16A 0.6277(15) 0.1820(9) 0.0829(3) 0.0246(18) Uani d PDU 0.610(6) 1 A 1
H H16A 0.5789 0.2703 0.0805 0.030 Uiso calc PR 0.610(6) 1 A 1
C C17A 0.8141(15) 0.1543(10) 0.1054(3) 0.0190(18) Uani d PDU 0.610(6) 1 A 1
H H17A 0.8891 0.2246 0.1179 0.023 Uiso calc PR 0.610(6) 1 A 1
C C18A 0.2520(9) 0.2376(8) 0.03791(18) 0.0459(17) Uani d PDU 0.610(6) 1 A 1
H H18A 0.3556 0.2933 0.0267 0.055 Uiso calc PR 0.610(6) 1 A 1
H H18B 0.2271 0.2745 0.0632 0.055 Uiso calc PR 0.610(6) 1 A 1
C C19A 0.0542(11) 0.2371(11) 0.0117(2) 0.061(2) Uani d PDU 0.610(6) 1 A 1
H H19A -0.0053 0.3262 0.0108 0.092 Uiso calc PR 0.610(6) 1 A 1
H H19B -0.0423 0.1745 0.0216 0.092 Uiso calc PR 0.610(6) 1 A 1
H H19C 0.0832 0.2104 -0.0141 0.092 Uiso calc PR 0.610(6) 1 A 1
O O1B 0.3343(14) 0.1530(7) 0.0407(3) 0.0238(16) Uani d PDU 0.390(6) 1 A 2
C C11B 1.076(4) -0.005(3) 0.1270(9) 0.019(3) Uani d PDU 0.390(6) 1 A 2
H H11B 1.1013 -0.0980 0.1272 0.023 Uiso calc PR 0.390(6) 1 A 2
C C12B 0.883(3) 0.0408(17) 0.1054(8) 0.019(2) Uani d PDU 0.390(6) 1 A 2
C C13B 0.748(3) -0.0595(16) 0.0880(7) 0.022(2) Uani d PDU 0.390(6) 1 A 2
H H13B 0.7842 -0.1504 0.0903 0.026 Uiso calc PR 0.390(6) 1 A 2
C C14B 0.561(3) -0.0215(13) 0.0672(6) 0.022(2) Uani d PDU 0.390(6) 1 A 2
H H14B 0.4692 -0.0872 0.0564 0.027 Uiso calc PR 0.390(6) 1 A 2
C C15B 0.512(2) 0.1117(12) 0.0627(6) 0.0188(19) Uani d PDU 0.390(6) 1 A 2
C C16B 0.647(2) 0.2108(13) 0.0783(5) 0.020(2) Uani d PDU 0.390(6) 1 A 2
H H16B 0.6125 0.3016 0.0747 0.024 Uiso calc PR 0.390(6) 1 A 2
C C17B 0.831(2) 0.1749(15) 0.0993(5) 0.017(2) Uani d PDU 0.390(6) 1 A 2
H H17B 0.9209 0.2421 0.1094 0.020 Uiso calc PR 0.390(6) 1 A 2
C C18B 0.1886(13) 0.0568(9) 0.0237(3) 0.038(2) Uani d PDU 0.390(6) 1 A 2
H H18C 0.1379 -0.0008 0.0436 0.046 Uiso calc PR 0.390(6) 1 A 2
H H18D 0.2530 0.0005 0.0050 0.046 Uiso calc PR 0.390(6) 1 A 2
C C19B 0.0125(13) 0.1380(12) 0.0035(3) 0.038(2) Uani d PDU 0.390(6) 1 A 2
H H19D -0.0927 0.0778 -0.0080 0.057 Uiso calc PR 0.390(6) 1 A 2
H H19E 0.0647 0.1929 -0.0165 0.057 Uiso calc PR 0.390(6) 1 A 2
H H19F -0.0468 0.1950 0.0223 0.057 Uiso calc PR 0.390(6) 1 A 2
S S1 0.97568(10) 0.53446(7) 0.16403(2) 0.02062(19) Uani d . 1 1 . .
F F1 0.3508(3) 0.6116(3) 0.03020(7) 0.0605(7) Uani d . 1 1 . .
O O2 0.8648(3) 0.5242(2) 0.19899(6) 0.0262(5) Uani d . 1 1 . .
O O3 1.0931(3) 0.4139(2) 0.15628(7) 0.0337(6) Uani d . 1 1 . .
O O4 1.0969(3) 0.6584(2) 0.16254(6) 0.0261(5) Uani d . 1 1 . .
C C21 0.7812(4) 0.5484(3) 0.12372(9) 0.0223(6) Uani d . 1 1 . .
C C22 0.8393(5) 0.5361(4) 0.08595(10) 0.0331(8) Uani d . 1 1 . .
H H22A 0.9763 0.5141 0.0820 0.040 Uiso calc R 1 1 . .
C C23 0.6945(5) 0.5564(4) 0.05408(11) 0.0436(10) Uani d . 1 1 . .
H H23A 0.7320 0.5488 0.0287 0.052 Uiso calc R 1 1 . .
C C24 0.4930(5) 0.5883(4) 0.06144(11) 0.0378(9) Uani d . 1 1 . .
C C25 0.4299(5) 0.5984(3) 0.09833(10) 0.0286(7) Uani d . 1 1 . .
H H25A 0.2922 0.6191 0.1021 0.034 Uiso calc R 1 1 . .
C C26 0.5755(4) 0.5771(3) 0.12989(9) 0.0212(6) Uani d . 1 1 . .
H H26A 0.5355 0.5819 0.1552 0.025 Uiso calc R 1 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0140(11) 0.0130(11) 0.0247(13) -0.0001(8) 0.0009(9) -0.0002(10)
C1 0.0109(12) 0.0221(13) 0.0181(15) 0.0002(10) 0.0016(10) -0.0002(11)
C2 0.0206(14) 0.0151(13) 0.0278(17) 0.0008(11) 0.0031(12) -0.0024(12)
C3 0.0174(14) 0.0256(15) 0.0268(17) -0.0101(12) 0.0008(12) -0.0069(13)
C4 0.0159(13) 0.0268(16) 0.0209(16) 0.0014(11) -0.0011(11) 0.0017(12)
C5 0.0213(14) 0.0170(13) 0.0231(16) 0.0033(11) 0.0013(12) 0.0011(12)
C6 0.0154(13) 0.0196(14) 0.0201(15) -0.0023(11) 0.0006(11) -0.0027(12)
C7 0.0193(14) 0.0132(13) 0.0250(16) -0.0004(10) 0.0031(11) -0.0014(11)
C8 0.0167(13) 0.0167(13) 0.0261(17) -0.0056(11) 0.0019(12) -0.0019(12)
C9 0.0100(12) 0.0209(13) 0.0184(14) -0.0014(11) 0.0026(10) -0.0023(12)
C10 0.0144(13) 0.0206(14) 0.0242(16) 0.0010(11) 0.0020(11) -0.0012(12)
C20 0.0198(14) 0.0152(13) 0.0371(19) 0.0009(11) -0.0052(13) 0.0016(13)
O1A 0.019(2) 0.065(3) 0.030(2) 0.010(3) -0.0085(17) 0.005(3)
C11A 0.013(3) 0.019(3) 0.018(5) 0.005(2) -0.001(3) 0.003(3)
C12A 0.013(2) 0.024(3) 0.015(3) 0.006(2) 0.000(2) 0.004(3)
C13A 0.018(3) 0.026(3) 0.026(3) 0.003(2) -0.006(2) 0.005(3)
C14A 0.019(3) 0.027(3) 0.029(3) 0.004(3) -0.003(2) -0.002(3)
C15A 0.016(2) 0.035(4) 0.022(2) 0.006(3) -0.003(2) 0.003(3)
C16A 0.019(3) 0.026(4) 0.030(3) 0.010(3) 0.005(2) 0.008(3)
C17A 0.014(3) 0.025(4) 0.018(3) 0.000(2) 0.004(2) 0.003(3)
C18A 0.029(3) 0.077(4) 0.030(3) 0.035(3) -0.002(2) 0.009(3)
C19A 0.037(3) 0.110(6) 0.036(4) 0.033(4) -0.006(3) 0.005(4)
O1B 0.021(3) 0.023(3) 0.026(3) -0.008(3) -0.006(2) 0.003(3)
C11B 0.018(4) 0.022(5) 0.017(5) -0.004(4) 0.000(4) 0.002(4)
C12B 0.011(3) 0.027(4) 0.019(4) 0.000(3) 0.001(3) 0.003(3)
C13B 0.021(4) 0.018(4) 0.025(4) 0.003(3) -0.001(3) 0.003(4)
C14B 0.019(4) 0.025(4) 0.021(3) -0.002(4) -0.008(3) 0.001(4)
C15B 0.015(3) 0.022(4) 0.019(3) 0.006(3) 0.002(3) 0.004(3)
C16B 0.015(3) 0.019(4) 0.026(4) -0.001(3) 0.005(3) 0.005(3)
C17B 0.013(3) 0.015(4) 0.023(4) -0.001(3) 0.004(3) 0.008(3)
C18B 0.031(4) 0.046(4) 0.036(4) -0.007(3) -0.002(3) 0.002(4)
C19B 0.017(4) 0.057(5) 0.039(5) 0.006(4) -0.007(3) 0.013(4)
S1 0.0126(3) 0.0153(3) 0.0329(4) 0.0008(3) -0.0040(3) -0.0043(3)
F1 0.0400(13) 0.096(2) 0.0406(14) 0.0180(13) -0.0222(10) -0.0190(13)
O2 0.0217(10) 0.0269(11) 0.0298(13) -0.0014(9) 0.0015(9) 0.0035(10)
O3 0.0195(11) 0.0232(11) 0.0559(16) 0.0070(9) -0.0105(10) -0.0129(11)
O4 0.0193(10) 0.0225(11) 0.0355(13) -0.0056(8) -0.0031(9) -0.0040(9)
C21 0.0145(13) 0.0160(13) 0.0353(18) -0.0031(11) -0.0050(12) -0.0068(13)
C22 0.0163(14) 0.049(2) 0.0331(19) 0.0027(14) -0.0005(13) -0.0184(17)
C23 0.0313(18) 0.067(3) 0.032(2) 0.0029(18) -0.0008(15) -0.0210(19)
C24 0.0289(17) 0.048(2) 0.033(2) 0.0046(16) -0.0146(15) -0.0118(17)
C25 0.0139(14) 0.0277(16) 0.043(2) 0.0015(12) -0.0054(13) -0.0066(15)
C26 0.0171(13) 0.0151(13) 0.0311(17) -0.0014(11) 0.0011(12) -0.0029(12)
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'
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
C9 N1 C1 121.7(2)
C9 N1 C20 119.0(2)
C1 N1 C20 119.3(2)
C6 C1 N1 118.7(2)
C6 C1 C2 119.5(2)
N1 C1 C2 121.8(2)
C3 C2 C1 118.3(3)
C3 C2 H2A 120.8
C1 C2 H2A 120.8
C2 C3 C4 122.6(3)
C2 C3 H3A 118.7
C4 C3 H3A 118.7
C5 C4 C3 118.9(3)
C5 C4 H4A 120.6
C3 C4 H4A 120.6
C4 C5 C6 121.0(3)
C4 C5 H5A 119.5
C6 C5 H5A 119.5
C5 C6 C1 119.6(2)
C5 C6 C7 121.3(3)
C1 C6 C7 119.1(2)
C8 C7 C6 120.6(3)
C8 C7 H7A 119.7
C6 C7 H7A 119.7
C7 C8 C9 121.0(2)
C7 C8 H8A 119.5
C9 C8 H8A 119.5
N1 C9 C8 118.8(2)
N1 C9 C10 119.6(2)
C8 C9 C10 121.6(2)
C11A C10 C9 121.2(6)
C11B C10 C9 127.1(10)
C11A C10 H10A 119.1
C11B C10 H10A 112.9
C9 C10 H10A 119.8
C11A C10 H10B 121.6
C11B C10 H10B 115.8
C9 C10 H10B 117.1
N1 C20 H20A 109.5
N1 C20 H20B 109.5
H20A C20 H20B 109.5
N1 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C15A O1A C18A 117.4(6)
C10 C11A C12A 124.9(12)
C10 C11A H11A 117.5
C12A C11A H11A 117.5
C13A C12A C17A 117.9(7)
C13A C12A C11A 118.9(8)
C17A C12A C11A 123.2(9)
C14A C13A C12A 121.6(7)
C14A C13A H13A 119.2
C12A C13A H13A 119.2
C15A C14A C13A 119.9(7)
C15A C14A H14A 120.0
C13A C14A H14A 120.0
O1A C15A C14A 117.2(7)
O1A C15A C16A 122.7(7)
C14A C15A C16A 120.0(7)
C15A C16A C17A 119.9(7)
C15A C16A H16A 120.0
C17A C16A H16A 120.0
C16A C17A C12A 120.5(7)
C16A C17A H17A 119.7
C12A C17A H17A 119.7
O1A C18A C19A 108.5(6)
O1A C18A H18A 110.0
C19A C18A H18A 110.0
O1A C18A H18B 110.0
C19A C18A H18B 110.0
H18A C18A H18B 108.4
C15B O1B C18B 120.8(8)
C10 C11B C12B 127(2)
C10 C11B H11B 116.7
C12B C11B H11B 116.7
C17B C12B C13B 118.3(11)
C17B C12B C11B 124.3(14)
C13B C12B C11B 117.2(13)
C14B C13B C12B 119.8(11)
C14B C13B H13B 120.1
C12B C13B H13B 120.1
C15B C14B C13B 119.8(11)
C15B C14B H14B 120.1
C13B C14B H14B 120.1
C14B C15B O1B 121.5(10)
C14B C15B C16B 120.8(10)
O1B C15B C16B 117.6(9)
C17B C16B C15B 120.0(10)
C17B C16B H16B 120.0
C15B C16B H16B 120.0
C16B C17B C12B 121.1(11)
C16B C17B H17B 119.5
C12B C17B H17B 119.5
O1B C18B C19B 105.9(8)
O1B C18B H18C 110.6
C19B C18B H18C 110.6
O1B C18B H18D 110.6
C19B C18B H18D 110.6
H18C C18B H18D 108.7
C18B C19B H19D 109.5
C18B C19B H19E 109.5
H19D C19B H19E 109.5
C18B C19B H19F 109.5
H19D C19B H19F 109.5
H19E C19B H19F 109.5
O3 S1 O2 113.38(14)
O3 S1 O4 113.36(13)
O2 S1 O4 113.04(13)
O3 S1 C21 105.18(13)
O2 S1 C21 106.51(13)
O4 S1 C21 104.35(13)
C22 C21 C26 120.1(3)
C22 C21 S1 119.3(2)
C26 C21 S1 120.6(2)
C21 C22 C23 120.5(3)
C21 C22 H22A 119.8
C23 C22 H22A 119.8
C24 C23 C22 117.7(3)
C24 C23 H23A 121.2
C22 C23 H23A 121.2
F1 C24 C25 118.8(3)
F1 C24 C23 118.0(3)
C25 C24 C23 123.2(3)
C24 C25 C26 118.5(3)
C24 C25 H25A 120.7
C26 C25 H25A 120.7
C25 C26 C21 120.0(3)
C25 C26 H26A 120.0
C21 C26 H26A 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C9 1.359(3)
N1 C1 1.407(3)
N1 C20 1.473(3)
C1 C6 1.407(4)
C1 C2 1.414(4)
C2 C3 1.383(4)
C2 H2A 0.9300
C3 C4 1.394(4)
C3 H3A 0.9300
C4 C5 1.366(4)
C4 H4A 0.9300
C5 C6 1.406(4)
C5 H5A 0.9300
C6 C7 1.411(4)
C7 C8 1.350(4)
C7 H7A 0.9300
C8 C9 1.418(4)
C8 H8A 0.9300
C9 C10 1.457(4)
C10 C11A 1.326(18)
C10 C11B 1.38(3)
C10 H10A 0.9600
C10 H10B 0.9600
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
O1A C15A 1.371(7)
O1A C18A 1.475(8)
C11A C12A 1.467(8)
C11A H11A 0.9300
C12A C13A 1.392(8)
C12A C17A 1.403(8)
C13A C14A 1.388(8)
C13A H13A 0.9300
C14A C15A 1.375(8)
C14A H14A 0.9300
C15A C16A 1.394(9)
C16A C17A 1.394(8)
C16A H16A 0.9300
C17A H17A 0.9300
C18A C19A 1.492(8)
C18A H18A 0.9700
C18A H18B 0.9700
C19A H19A 0.9600
C19A H19B 0.9600
C19A H19C 0.9600
O1B C15B 1.375(11)
O1B C18B 1.425(10)
C11B C12B 1.463(12)
C11B H11B 0.9300
C12B C17B 1.380(12)
C12B C13B 1.417(12)
C13B C14B 1.399(12)
C13B H13B 0.9300
C14B C15B 1.360(11)
C14B H14B 0.9300
C15B C16B 1.385(11)
C16B C17B 1.377(11)
C16B H16B 0.9300
C17B H17B 0.9300
C18B C19B 1.506(10)
C18B H18C 0.9700
C18B H18D 0.9700
C19B H19D 0.9600
C19B H19E 0.9600
C19B H19F 0.9600
S1 O3 1.449(2)
S1 O2 1.454(2)
S1 O4 1.457(2)
S1 C21 1.788(3)
F1 C24 1.367(4)
C21 C22 1.388(5)
C21 C26 1.389(4)
C22 C23 1.388(5)
C22 H22A 0.9300
C23 C24 1.380(5)
C23 H23A 0.9300
C24 C25 1.369(5)
C25 C26 1.385(4)
C25 H25A 0.9300
C26 H26A 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2A O2 1_655 0.93 2.55 3.456(4) 166 y
C8 H8A O4 1_545 0.93 2.41 3.306(3) 161 y
C10 H10A O3 1_555 0.96 2.55 3.483(4) 164 y
C11A H11A O4 1_545 0.93 2.52 3.408(19) 159 y
C17A H17A O3 1_555 0.93 2.58 3.510(10) 177 y
C20 H20B O2 1_655 0.96 2.53 3.441(4) 158 y
C20 H20C O3 1_555 0.96 2.44 3.085(4) 124 y
C25 H25A O4 1_455 0.93 2.55 3.264(4) 134 y
C13A H13A Cg5 1_545 0.93 2.82 3.575(10) 139 y
C16A H16A Cg5 1_555 0.93 2.98 3.826(9) 151 y
C19A H19B Cg4 1_455 0.96 2.99 3.862(11) 152 y
C13B H13B Cg5 1_545 0.93 2.95 3.765(16) 147 y
C16B H16B Cg5 1_555 0.93 2.70 3.562(13) 155 y
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
C9 N1 C1 C6 1.9(4)
C20 N1 C1 C6 -177.6(3)
C9 N1 C1 C2 -178.2(3)
C20 N1 C1 C2 2.4(4)
C6 C1 C2 C3 -1.3(4)
N1 C1 C2 C3 178.7(3)
C1 C2 C3 C4 2.1(5)
C2 C3 C4 C5 -0.7(5)
C3 C4 C5 C6 -1.5(5)
C4 C5 C6 C1 2.2(4)
C4 C5 C6 C7 -176.9(3)
N1 C1 C6 C5 179.2(3)
C2 C1 C6 C5 -0.8(4)
N1 C1 C6 C7 -1.7(4)
C2 C1 C6 C7 178.4(3)
C5 C6 C7 C8 179.0(3)
C1 C6 C7 C8 -0.2(4)
C6 C7 C8 C9 1.9(5)
C1 N1 C9 C8 -0.2(4)
C20 N1 C9 C8 179.3(3)
C1 N1 C9 C10 179.8(3)
C20 N1 C9 C10 -0.7(4)
C7 C8 C9 N1 -1.7(4)
C7 C8 C9 C10 178.3(3)
N1 C9 C10 C11A 178.9(12)
C8 C9 C10 C11A -1.0(12)
N1 C9 C10 C11B 173(2)
C8 C9 C10 C11B -7(2)
C11B C10 C11A C12A -36(15)
C9 C10 C11A C12A -178.3(12)
C10 C11A C12A C13A 173.8(18)
C10 C11A C12A C17A -8(2)
C17A C12A C13A C14A 4(2)
C11A C12A C13A C14A -177.8(15)
C12A C13A C14A C15A -2(2)
C18A O1A C15A C14A 179.0(10)
C18A O1A C15A C16A 2.5(15)
C13A C14A C15A O1A -177.8(12)
C13A C14A C15A C16A -1.2(18)
O1A C15A C16A C17A 178.5(10)
C14A C15A C16A C17A 2.1(16)
C15A C16A C17A C12A 0.1(15)
C13A C12A C17A C16A -3.0(17)
C11A C12A C17A C16A 178.8(13)
C15A O1A C18A C19A 177.1(8)
C11A C10 C11B C12B 140(19)
C9 C10 C11B C12B -179.0(19)
C10 C11B C12B C17B 6(4)
C10 C11B C12B C13B -178(3)
C17B C12B C13B C14B -4(3)
C11B C12B C13B C14B 180(2)
C12B C13B C14B C15B 2(3)
C13B C14B C15B O1B 176.6(19)
C13B C14B C15B C16B 0(3)
C18B O1B C15B C14B 3(2)
C18B O1B C15B C16B 180.0(14)
C14B C15B C16B C17B -1(3)
O1B C15B C16B C17B -177.5(16)
C15B C16B C17B C12B -1(3)
C13B C12B C17B C16B 3(3)
C11B C12B C17B C16B 180(2)
C15B O1B C18B C19B 177.8(12)
O3 S1 C21 C22 -48.2(3)
O2 S1 C21 C22 -168.8(2)
O4 S1 C21 C22 71.3(3)
O3 S1 C21 C26 134.5(2)
O2 S1 C21 C26 13.9(3)
O4 S1 C21 C26 -105.9(2)
C26 C21 C22 C23 2.0(5)
S1 C21 C22 C23 -175.2(3)
C21 C22 C23 C24 -0.3(6)
C22 C23 C24 F1 178.5(3)
C22 C23 C24 C25 -1.1(6)
F1 C24 C25 C26 -178.9(3)
C23 C24 C25 C26 0.7(6)
C24 C25 C26 C21 1.1(4)
C22 C21 C26 C25 -2.4(4)
S1 C21 C26 C25 174.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139086363