#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/90/2239022.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_2239022
loop_
_publ_author_name
'Yamuna, Thammarse S.'
'Kaur, Manpreet'
'Anderson, Brian J.'
'Jasinski, Jerry P.'
'Yathirajan, H.S.'
_publ_section_title
;
 Flupentixol tartrate
;
_journal_coeditor_code           SU2691
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o206
_journal_page_last               o207
_journal_paper_doi               10.1107/S1600536814001536
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C23 H26 F3 N2 O S +, C4 H5 O6 -'
_chemical_formula_moiety         'C23 H26 F3 N2 O S +, C4 H5 O6 -'
_chemical_formula_sum            'C27 H31 F3 N2 O7 S'
_chemical_formula_weight         584.60
_chemical_name_common
;
Flupentixol tartrate
;
_chemical_name_systematic
'1-(2-Hydroxyethyl)-4-{3-[2-(trifluoromethyl)thioxanthen-9-ylidene]propyl}piperazin-1-ium 3-carboxy-2,3-dihydroxypropionate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.617(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9239(3)
_cell_length_b                   9.1968(3)
_cell_length_c                   30.0099(8)
_cell_measurement_reflns_used    5128
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.4709
_cell_measurement_theta_min      2.9623
_cell_volume                     2720.70(14)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis RED (Agilent, 2012)'
_computing_molecular_graphics    'OLEX2 (Dolomanov <i>et al.</i>, 2009)'
_computing_publication_material  'OLEX2 (Dolomanov <i>et al.</i>, 2009)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2008)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Agilent Gemini EOS'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            16827
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.622
_diffrn_reflns_theta_min         2.965
_exptl_absorpt_coefficient_mu    1.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO and CrysAlis RED; Agilent, 2012).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.712
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0779
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0775P)^2^+5.4936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1960
_refine_ls_wR_factor_ref         0.2057
_reflns_number_gt                4331
_reflns_number_total             5325
_reflns_threshold_expression     I>2\s(I)
_iucr_refine_instructions_details
;
TITL HSY-615 in P21/n #14
CELL 1.54184 9.92385 9.19678 30.00991 90 96.6171 90
ZERR 4 0.00025 0.00027 0.00084 0 0.0026 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O F S
UNIT 108 124 8 28 12 4
EQIV $1 -1+X,+Y,+Z
EQIV $2 -X,1-Y,1-Z
EQIV $3 1-X,1-Y,1-Z
EQIV $4 1-X,-Y,1-Z
EQIV $5 1.5-X,0.5+Y,0.5-Z
EQIV $6 0.5+X,0.5-Y,-0.5+Z
L.S. 30
PLAN  15
HTAB O1A O1B_$1
HTAB N2A O2B_$1
HTAB C1A O2B_$1
HTAB C2A O1A_$2
HTAB C2A O2B_$3
HTAB C2A O6B
HTAB C3A O5B
HTAB C3A O6B
HTAB C4A O2B_$1
HTAB C4A O1B_$4
HTAB C5A O2B_$3
HTAB C14A F3A_$5
HTAB C15A O1A_$6
HTAB O3B O5B_$4
HTAB O4B O3B_$4
HTAB O6B N1A
HTAB C3B F2AB
REM reset to P21/n #14
BOND $H
MORE -1
fmap 2
acta
CONF
OMIT 0 2 0
OMIT -4 2 33
OMIT -4 1 35
OMIT -2 2 36
OMIT -6 0 34
OMIT 1 2 3
REM <HKL>H:/Prof.Yathirajan%202013/HSY-615/HSY-615-mk/HSY-615.hkl</HKL>
WGHT    0.077500    5.493600
FVAR       3.92841   0.53548   0.66869   0.71638
S1A   6    0.222634    0.192667    0.152781    11.00000    0.08201    0.04747 =
         0.04690    0.00747    0.01499    0.00685
PART 1
F1A   5    0.740729    0.033063    0.303509    21.00000    0.04183    0.11468 =
         0.12620    0.02917   -0.03016   -0.02924
PART 0
PART 2
F1AB  5    0.758163   -0.042345    0.290029   -21.00000    0.07320    0.39450 =
         0.15276    0.11460    0.02364   -0.00494
PART 0
PART 1
F2A   5    0.594116   -0.076813    0.333416    41.00000    0.04389    0.17314 =
         0.06865    0.04551    0.00364    0.01326
PART 0
PART 2
F2AB  5    0.675919    0.032853    0.331585   -41.00000    0.40241    0.18012 =
         0.07664   -0.06946   -0.04494    0.11606
PART 0
PART 1
F3A   5    0.684398   -0.177005    0.280926    31.00000    0.12876    0.09929 =
         0.14582   -0.01293   -0.02268    0.07748
PART 0
PART 2
F3AB  5    0.623526   -0.181995    0.308691   -31.00000    0.15248    0.19403 =
         0.32077    0.18569   -0.10298   -0.12325
PART 0
O1A   4    0.014846    0.296159    0.582595    11.00000    0.02868    0.05455 =
         0.03795   -0.01164    0.00343    0.00545
AFIX 147
H1A   2   -0.053251    0.268353    0.566823    11.00000   -1.50000
AFIX   0
N1A   3    0.131273    0.233047    0.390162    11.00000    0.02819    0.03248 =
         0.03188   -0.00021    0.00570    0.00364
N2A   3    0.112086    0.286893    0.484733    11.00000    0.02117    0.02927 =
         0.02962   -0.00009    0.00489    0.00161
H2A   2    0.015091    0.289364    0.484533    11.00000    0.03592
C1A   1    0.089063    0.376081    0.405845    11.00000    0.02663    0.02936 =
         0.03613    0.00420    0.00491    0.00440
AFIX  23
H1AA  2   -0.009019    0.379588    0.404470    11.00000   -1.20000
H1AB  2    0.117658    0.451868    0.386511    11.00000   -1.20000
AFIX   0
C2A   1    0.151792    0.401790    0.453523    11.00000    0.02890    0.02768 =
         0.03599    0.00174    0.00313   -0.00071
AFIX  23
H2AA  2    0.249790    0.403292    0.454375    11.00000   -1.20000
H2AB  2    0.123164    0.495973    0.463534    11.00000   -1.20000
AFIX   0
C3A   1    0.142168    0.139404    0.467239    11.00000    0.02753    0.02647 =
         0.03602    0.00042    0.00680    0.00353
AFIX  23
H3AA  2    0.105826    0.065793    0.485688    11.00000   -1.20000
H3AB  2    0.239648    0.126016    0.469338    11.00000   -1.20000
AFIX   0
C4A   1    0.082049    0.119867    0.419325    11.00000    0.02989    0.02941 =
         0.03789   -0.00278    0.00760    0.00045
AFIX  23
H4AA  2    0.106281    0.024659    0.408843    11.00000   -1.20000
H4AB  2   -0.016060    0.124822    0.417547    11.00000   -1.20000
AFIX   0
C5A   1    0.185801    0.313428    0.530708    11.00000    0.02583    0.03559 =
         0.03284   -0.00279   -0.00262    0.00386
AFIX  23
H5AA  2    0.181552    0.416437    0.537349    11.00000   -1.20000
H5AB  2    0.280548    0.288184    0.530284    11.00000   -1.20000
AFIX   0
C6A   1    0.130709    0.228828    0.568337    11.00000    0.02674    0.04066 =
         0.03359    0.00115    0.00025    0.00697
AFIX  23
H6AA  2    0.107311    0.131125    0.558002    11.00000   -1.20000
H6AB  2    0.200768    0.221326    0.593587    11.00000   -1.20000
AFIX   0
C7A   1    0.079514    0.211053    0.342759    11.00000    0.03891    0.04577 =
         0.03187   -0.00061    0.00381   -0.00053
AFIX  23
H7AA  2    0.083193    0.302199    0.326680    11.00000   -1.20000
H7AB  2   -0.014466    0.180103    0.340515    11.00000   -1.20000
AFIX   0
C8A   1    0.164416    0.094897    0.321088    11.00000    0.03617    0.06243 =
         0.04613   -0.00082    0.00046    0.00479
AFIX  23
H8AA  2    0.254181    0.132973    0.318250    11.00000   -1.20000
H8AB  2    0.174359    0.009242    0.340042    11.00000   -1.20000
AFIX   0
C9A   1    0.096569    0.055301    0.276444    11.00000    0.03706    0.05977 =
         0.04454   -0.00532    0.00447    0.00369
AFIX  43
H9A   2    0.003450    0.040494    0.274932    11.00000   -1.20000
AFIX   0
C10A  1    0.149650    0.037564    0.237736    11.00000    0.04925    0.04180 =
         0.04735    0.00001    0.00928    0.00747
C11A  1    0.297059    0.049557    0.233096    11.00000    0.05537    0.03774 =
         0.03815   -0.00530    0.01419   -0.00106
C12A  1    0.397338   -0.007404    0.265026    11.00000    0.04761    0.04416 =
         0.04148   -0.00037    0.01784    0.00523
AFIX  43
H12A  2    0.371891   -0.057214    0.289698    11.00000   -1.20000
AFIX   0
C13A  1    0.533967    0.009307    0.260427    11.00000    0.05023    0.04979 =
         0.05397   -0.00998    0.01291   -0.00122
C14A  1    0.573642    0.080851    0.223603    11.00000    0.05763    0.05166 =
         0.06500   -0.01274    0.02758   -0.01598
AFIX  43
H14A  2    0.665182    0.089833    0.220117    11.00000   -1.20000
AFIX   0
C15A  1    0.475508    0.139313    0.191796    11.00000    0.06622    0.06199 =
         0.03827    0.00779    0.01610   -0.01969
AFIX  43
H15A  2    0.501977    0.191550    0.167735    11.00000   -1.20000
AFIX   0
C16A  1    0.338889    0.120609    0.195556    11.00000    0.06996    0.03619 =
         0.04106   -0.00622    0.01730   -0.00076
C17A  1    0.077258    0.080484    0.156524    11.00000    0.06803    0.04270 =
         0.04986   -0.00458    0.00992    0.02150
C18A  1   -0.016140    0.069081    0.119393    11.00000    0.09245    0.05792 =
         0.04823   -0.00258   -0.00009    0.03031
AFIX  43
H18A  2   -0.002155    0.118918    0.093355    11.00000   -1.20000
AFIX   0
C19A  1   -0.131185   -0.015717    0.120103    11.00000    0.05535    0.05690 =
         0.07200   -0.01020   -0.01241    0.01629
AFIX  43
H19A  2   -0.195821   -0.021122    0.095127    11.00000   -1.20000
AFIX   0
C20A  1   -0.147945   -0.092617    0.158987    11.00000    0.04976    0.07260 =
         0.06293   -0.01844   -0.01291    0.00951
AFIX  43
H20A  2   -0.222922   -0.152948    0.159588    11.00000   -1.20000
AFIX   0
C21A  1   -0.056518   -0.080870    0.196029    11.00000    0.05226    0.05240 =
         0.06048   -0.00386    0.00747    0.00471
AFIX  43
H21A  2   -0.069798   -0.133726    0.221580    11.00000   -1.20000
AFIX   0
C22A  1    0.059146    0.010468    0.196644    11.00000    0.04974    0.04650 =
         0.04591   -0.00619    0.00730    0.01092
C23A  1    0.636669   -0.054603    0.295406    11.00000    0.04066    0.07271 =
         0.08055   -0.00240    0.01263    0.00222
O1B   4    0.793329    0.201273    0.533271    11.00000    0.03203    0.04876 =
         0.04362    0.01027   -0.00278   -0.00567
O2B   4    0.841896    0.310858    0.470592    11.00000    0.02156    0.04176 =
         0.04272    0.00173    0.00395   -0.00110
O3B   4    0.533134    0.193463    0.509502    11.00000    0.02293    0.04550 =
         0.03725    0.00412    0.00685    0.00307
AFIX 147
H3B   2    0.582878    0.159376    0.530646    11.00000   -1.50000
AFIX   0
O4B   4    0.656702   -0.000789    0.449609    11.00000    0.02494    0.03618 =
         0.05279   -0.00160    0.00202    0.00688
AFIX 147
H4B   2    0.599904   -0.049964    0.460537    11.00000   -1.50000
AFIX   0
O5B   4    0.392923    0.003679    0.416142    11.00000    0.02634    0.03804 =
         0.04668    0.00233   -0.00030    0.00078
O6B   4    0.397708    0.242735    0.402856    11.00000    0.02200    0.04092 =
         0.05129    0.01057    0.00038    0.00069
AFIX 147
H6B   2    0.316532    0.231039    0.394992    11.00000   -1.50000
AFIX   0
C1B   1    0.762803    0.251779    0.495181    11.00000    0.02365    0.02805 =
         0.03827   -0.00331    0.00186    0.00082
C2B   1    0.612692    0.241775    0.476007    11.00000    0.02088    0.03210 =
         0.03782    0.00355    0.00508    0.00222
AFIX  13
H2B   2    0.580936    0.337918    0.465338    11.00000   -1.20000
AFIX   0
C3B   1    0.600358    0.135083    0.436395    11.00000    0.01999    0.03751 =
         0.03880    0.00127    0.00394    0.00311
AFIX  13
H3BA  2    0.651060    0.174913    0.413027    11.00000   -1.20000
AFIX   0
C4B   1    0.452249    0.118556    0.416854    11.00000    0.02243    0.03727 =
         0.03041    0.00368    0.00575    0.00371
HKLF 4
REM  HSY-615 in P21/n #14
REM R1 =  0.0779 for    4331 Fo > 4sig(Fo)  and  0.0937 for all    5325 data
REM    399 parameters refined using      0 restraints
END
WGHT      0.0777      5.4425
REM Highest difference peak  0.664,  deepest hole -0.712,  1-sigma level  0.066
Q1    1   0.4537  0.2264  0.2025  11.00000  0.05    0.66
Q2    1   0.2963  0.2020  0.1733  11.00000  0.05    0.66
Q3    1   0.0554  0.0902  0.3110  11.00000  0.05    0.65
Q4    1   0.1945  0.0672  0.2937  11.00000  0.05    0.49
Q5    1   0.2441  0.0555  0.2593  11.00000  0.05    0.47
Q6    1  -0.0892 -0.0128  0.1484  11.00000  0.05    0.42
Q7    1   0.1238  0.2920  0.5094  11.00000  0.05    0.35
Q8    1  -0.1110 -0.1900  0.1660  11.00000  0.05    0.34
Q9    1  -0.2088  0.0739  0.1604  11.00000  0.05    0.32
Q10   1   0.0019  0.2389  0.3353  11.00000  0.05    0.31
Q11   1   0.1551  0.2796  0.5497  11.00000  0.05    0.30
Q12   1   0.6646  0.0590  0.2410  11.00000  0.05    0.28
Q13   1   0.4763  0.1471  0.1759  11.00000  0.05    0.28
Q14   1   0.4930 -0.0610  0.3073  11.00000  0.05    0.28
Q15   1   0.7736  0.2784  0.5292  11.00000  0.05    0.27
;
_cod_data_source_file            su2691sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2720.68(13)
_cod_database_code               2239022
_cod_database_fobs_code          2239022
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_hkl_checksum              94945
_shelx_res_checksum              23688
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1A 0.22263(14) 0.19267(13) 0.15278(4) 0.0582(3) Uani d 1 . .
F F1A 0.7407(15) 0.0331(16) 0.3035(8) 0.097(7) Uani d 0.54(6) A 1
F F1AB 0.758(2) -0.042(12) 0.2900(16) 0.21(2) Uani d 0.46(6) A 2
F F2A 0.5941(6) -0.0768(15) 0.3334(2) 0.095(4) Uani d 0.72(2) A 1
F F2AB 0.676(7) 0.033(5) 0.3316(9) 0.23(3) Uani d 0.28(2) A 2
F F3A 0.6844(14) -0.1770(13) 0.2809(4) 0.128(6) Uani d 0.67(3) A 1
F F3AB 0.624(4) -0.182(4) 0.3087(18) 0.23(3) Uani d 0.33(3) A 2
O O1A 0.0148(2) 0.2962(3) 0.58260(9) 0.0404(6) Uani d 1 . .
H H1A -0.0533 0.2684 0.5668 0.061 Uiso calc 1 . .
N N1A 0.1313(3) 0.2330(3) 0.39016(9) 0.0307(6) Uani d 1 . .
N N2A 0.1121(3) 0.2869(3) 0.48473(9) 0.0265(6) Uani d 1 . .
H H2A 0.015(4) 0.289(4) 0.4845(12) 0.036(10) Uiso d 1 . .
C C1A 0.0891(3) 0.3761(4) 0.40584(11) 0.0306(7) Uani d 1 . .
H H1AA -0.0090 0.3796 0.4045 0.037 Uiso calc 1 . .
H H1AB 0.1177 0.4519 0.3865 0.037 Uiso calc 1 . .
C C2A 0.1518(3) 0.4018(4) 0.45352(11) 0.0309(7) Uani d 1 . .
H H2AA 0.2498 0.4033 0.4544 0.037 Uiso calc 1 . .
H H2AB 0.1232 0.4960 0.4635 0.037 Uiso calc 1 . .
C C3A 0.1422(3) 0.1394(4) 0.46724(11) 0.0298(7) Uani d 1 . .
H H3AA 0.1058 0.0658 0.4857 0.036 Uiso calc 1 . .
H H3AB 0.2396 0.1260 0.4693 0.036 Uiso calc 1 . .
C C4A 0.0820(3) 0.1199(4) 0.41933(12) 0.0321(7) Uani d 1 . .
H H4AA 0.1063 0.0247 0.4088 0.039 Uiso calc 1 . .
H H4AB -0.0161 0.1248 0.4175 0.039 Uiso calc 1 . .
C C5A 0.1858(3) 0.3134(4) 0.53071(11) 0.0319(7) Uani d 1 . .
H H5AA 0.1816 0.4164 0.5373 0.038 Uiso calc 1 . .
H H5AB 0.2805 0.2882 0.5303 0.038 Uiso calc 1 . .
C C6A 0.1307(3) 0.2288(4) 0.56834(12) 0.0339(8) Uani d 1 . .
H H6AA 0.1073 0.1311 0.5580 0.041 Uiso calc 1 . .
H H6AB 0.2008 0.2213 0.5936 0.041 Uiso calc 1 . .
C C7A 0.0795(4) 0.2111(4) 0.34276(12) 0.0389(8) Uani d 1 . .
H H7AA 0.0832 0.3022 0.3267 0.047 Uiso calc 1 . .
H H7AB -0.0145 0.1801 0.3405 0.047 Uiso calc 1 . .
C C8A 0.1644(4) 0.0949(5) 0.32109(14) 0.0486(10) Uani d 1 . .
H H8AA 0.2542 0.1330 0.3183 0.058 Uiso calc 1 . .
H H8AB 0.1744 0.0092 0.3400 0.058 Uiso calc 1 . .
C C9A 0.0966(4) 0.0553(5) 0.27644(14) 0.0471(10) Uani d 1 . .
H H9A 0.0035 0.0405 0.2749 0.057 Uiso calc 1 . .
C C10A 0.1497(4) 0.0376(4) 0.23774(14) 0.0458(9) Uani d 1 . .
C C11A 0.2971(4) 0.0496(4) 0.23310(13) 0.0431(9) Uani d 1 . .
C C12A 0.3973(4) -0.0074(4) 0.26503(14) 0.0434(9) Uani d 1 . .
H H12A 0.3719 -0.0572 0.2897 0.052 Uiso calc 1 . .
C C13A 0.5340(5) 0.0093(5) 0.26043(15) 0.0508(10) Uani d 1 . .
C C14A 0.5736(5) 0.0809(5) 0.22360(16) 0.0565(12) Uani d 1 . .
H H14A 0.6652 0.0898 0.2201 0.068 Uiso calc 1 . .
C C15A 0.4755(5) 0.1393(5) 0.19180(14) 0.0547(11) Uani d 1 . .
H H15A 0.5020 0.1916 0.1677 0.066 Uiso calc 1 . .
C C16A 0.3389(5) 0.1206(4) 0.19556(14) 0.0482(10) Uani d 1 . .
C C17A 0.0773(5) 0.0805(5) 0.15652(15) 0.0533(11) Uani d 1 . .
C C18A -0.0161(6) 0.0691(6) 0.11939(16) 0.0668(14) Uani d 1 . .
H H18A -0.0022 0.1189 0.0934 0.080 Uiso calc 1 . .
C C19A -0.1312(5) -0.0157(6) 0.12010(18) 0.0630(13) Uani d 1 . .
H H19A -0.1958 -0.0211 0.0951 0.076 Uiso calc 1 . .
C C20A -0.1479(5) -0.0926(6) 0.15899(17) 0.0633(13) Uani d 1 . .
H H20A -0.2229 -0.1529 0.1596 0.076 Uiso calc 1 . .
C C21A -0.0565(5) -0.0809(5) 0.19603(16) 0.0550(11) Uani d 1 . .
H H21A -0.0698 -0.1337 0.2216 0.066 Uiso calc 1 . .
C C22A 0.0591(4) 0.0105(5) 0.19664(14) 0.0472(10) Uani d 1 . .
C C23A 0.6367(5) -0.0546(6) 0.2954(2) 0.0642(13) Uani d 1 . .
O O1B 0.7933(3) 0.2013(3) 0.53327(9) 0.0420(6) Uani d 1 . .
O O2B 0.8419(2) 0.3109(3) 0.47059(8) 0.0353(6) Uani d 1 . .
O O3B 0.5331(2) 0.1935(3) 0.50950(8) 0.0350(6) Uani d 1 . .
H H3B 0.5829 0.1594 0.5306 0.052 Uiso calc 1 . .
O O4B 0.6567(2) -0.0008(3) 0.44961(9) 0.0382(6) Uani d 1 . .
H H4B 0.5999 -0.0500 0.4605 0.057 Uiso calc 1 . .
O O5B 0.3929(2) 0.0037(3) 0.41614(9) 0.0374(6) Uani d 1 . .
O O6B 0.3977(2) 0.2427(3) 0.40286(9) 0.0384(6) Uani d 1 . .
H H6B 0.3165 0.2310 0.3950 0.058 Uiso calc 1 . .
C C1B 0.7628(3) 0.2518(4) 0.49518(12) 0.0301(7) Uani d 1 . .
C C2B 0.6127(3) 0.2418(4) 0.47601(11) 0.0301(7) Uani d 1 . .
H H2B 0.5809 0.3379 0.4653 0.036 Uiso calc 1 . .
C C3B 0.6004(3) 0.1351(4) 0.43639(12) 0.0321(7) Uani d 1 . .
H H3BA 0.6511 0.1749 0.4130 0.038 Uiso calc 1 . .
C C4B 0.4522(3) 0.1186(4) 0.41685(11) 0.0298(7) Uani d 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
S1A 0.0820(8) 0.0475(6) 0.0469(6) 0.0068(6) 0.0150(6) 0.0075(5)
F1A 0.042(6) 0.115(11) 0.126(12) -0.029(5) -0.030(7) 0.029(7)
F1AB 0.073(8) 0.39(6) 0.153(19) 0.00(2) 0.024(11) 0.11(3)
F2A 0.044(3) 0.173(10) 0.069(4) 0.013(4) 0.004(2) 0.046(5)
F2AB 0.40(7) 0.18(3) 0.077(15) 0.12(4) -0.04(3) -0.069(18)
F3A 0.129(10) 0.099(8) 0.146(8) 0.077(7) -0.023(6) -0.013(5)
F3AB 0.15(2) 0.19(3) 0.32(5) -0.12(2) -0.10(3) 0.19(3)
O1A 0.0287(12) 0.0545(16) 0.0379(14) 0.0055(12) 0.0034(10) -0.0116(12)
N1A 0.0282(14) 0.0325(15) 0.0319(15) 0.0036(11) 0.0057(11) -0.0002(12)
N2A 0.0212(13) 0.0293(14) 0.0296(14) 0.0016(11) 0.0049(11) -0.0001(11)
C1A 0.0266(16) 0.0294(17) 0.0361(18) 0.0044(13) 0.0049(14) 0.0042(14)
C2A 0.0289(16) 0.0277(16) 0.0360(18) -0.0007(13) 0.0031(14) 0.0017(13)
C3A 0.0275(16) 0.0265(16) 0.0360(18) 0.0035(13) 0.0068(14) 0.0004(13)
C4A 0.0299(17) 0.0294(17) 0.0379(19) 0.0004(14) 0.0076(14) -0.0028(14)
C5A 0.0258(16) 0.0356(18) 0.0328(18) 0.0039(14) -0.0026(13) -0.0028(14)
C6A 0.0267(16) 0.0407(19) 0.0336(18) 0.0070(14) 0.0002(14) 0.0012(15)
C7A 0.0389(19) 0.046(2) 0.0319(19) -0.0005(16) 0.0038(15) -0.0006(16)
C8A 0.036(2) 0.062(3) 0.046(2) 0.0048(19) 0.0005(17) -0.001(2)
C9A 0.037(2) 0.060(3) 0.045(2) 0.0037(19) 0.0045(17) -0.0053(19)
C10A 0.049(2) 0.042(2) 0.047(2) 0.0075(18) 0.0093(19) 0.0000(17)
C11A 0.055(2) 0.038(2) 0.038(2) -0.0011(18) 0.0142(18) -0.0053(16)
C12A 0.048(2) 0.044(2) 0.041(2) 0.0052(18) 0.0178(18) -0.0004(17)
C13A 0.050(2) 0.050(2) 0.054(3) -0.0012(19) 0.013(2) -0.010(2)
C14A 0.058(3) 0.052(3) 0.065(3) -0.016(2) 0.028(2) -0.013(2)
C15A 0.066(3) 0.062(3) 0.038(2) -0.020(2) 0.016(2) 0.008(2)
C16A 0.070(3) 0.036(2) 0.041(2) -0.0008(19) 0.017(2) -0.0062(17)
C17A 0.068(3) 0.043(2) 0.050(2) 0.022(2) 0.010(2) -0.0046(19)
C18A 0.092(4) 0.058(3) 0.048(3) 0.030(3) 0.000(3) -0.003(2)
C19A 0.055(3) 0.057(3) 0.072(3) 0.016(2) -0.012(2) -0.010(2)
C20A 0.050(3) 0.073(3) 0.063(3) 0.010(2) -0.013(2) -0.018(3)
C21A 0.052(3) 0.052(3) 0.060(3) 0.005(2) 0.007(2) -0.004(2)
C22A 0.050(2) 0.046(2) 0.046(2) 0.0109(19) 0.0073(19) -0.0062(18)
C23A 0.041(2) 0.073(3) 0.081(4) 0.002(2) 0.013(2) -0.002(3)
O1B 0.0320(13) 0.0488(15) 0.0436(15) -0.0057(11) -0.0028(11) 0.0103(12)
O2B 0.0216(11) 0.0418(14) 0.0427(14) -0.0011(10) 0.0039(10) 0.0017(11)
O3B 0.0229(11) 0.0455(14) 0.0373(14) 0.0031(10) 0.0068(10) 0.0041(11)
O4B 0.0249(11) 0.0362(13) 0.0528(16) 0.0069(10) 0.0020(11) -0.0016(11)
O5B 0.0263(12) 0.0380(14) 0.0467(15) 0.0008(10) -0.0003(10) 0.0023(11)
O6B 0.0220(11) 0.0409(14) 0.0513(16) 0.0007(10) 0.0004(11) 0.0106(12)
C1B 0.0237(15) 0.0280(16) 0.0383(19) 0.0008(13) 0.0019(14) -0.0033(14)
C2B 0.0209(15) 0.0321(17) 0.0378(19) 0.0022(13) 0.0051(13) 0.0035(14)
C3B 0.0200(15) 0.0375(18) 0.0388(19) 0.0031(13) 0.0039(13) 0.0013(15)
C4B 0.0224(15) 0.0373(18) 0.0304(17) 0.0037(14) 0.0058(13) 0.0037(14)
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 '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
C16A S1A C17A 101.7(2)
C23A F1AB F2AB 52(3)
C23A F2AB F1AB 46(2)
C6A O1A H1A 109.5
C1A N1A C4A 108.3(2)
C7A N1A C1A 110.6(3)
C7A N1A C4A 111.9(3)
C2A N2A H2A 108(2)
C2A N2A C3A 110.1(2)
C2A N2A C5A 108.9(3)
C3A N2A H2A 105(2)
C3A N2A C5A 111.9(3)
C5A N2A H2A 112(2)
N1A C1A H1AA 109.7
N1A C1A H1AB 109.7
N1A C1A C2A 109.9(3)
H1AA C1A H1AB 108.2
C2A C1A H1AA 109.7
C2A C1A H1AB 109.7
N2A C2A C1A 111.9(3)
N2A C2A H2AA 109.2
N2A C2A H2AB 109.2
C1A C2A H2AA 109.2
C1A C2A H2AB 109.2
H2AA C2A H2AB 107.9
N2A C3A H3AA 109.3
N2A C3A H3AB 109.3
N2A C3A C4A 111.8(3)
H3AA C3A H3AB 107.9
C4A C3A H3AA 109.3
C4A C3A H3AB 109.3
N1A C4A C3A 111.1(3)
N1A C4A H4AA 109.4
N1A C4A H4AB 109.4
C3A C4A H4AA 109.4
C3A C4A H4AB 109.4
H4AA C4A H4AB 108.0
N2A C5A H5AA 108.6
N2A C5A H5AB 108.6
N2A C5A C6A 114.7(3)
H5AA C5A H5AB 107.6
C6A C5A H5AA 108.6
C6A C5A H5AB 108.6
O1A C6A C5A 112.0(3)
O1A C6A H6AA 109.2
O1A C6A H6AB 109.2
C5A C6A H6AA 109.2
C5A C6A H6AB 109.2
H6AA C6A H6AB 107.9
N1A C7A H7AA 109.5
N1A C7A H7AB 109.5
N1A C7A C8A 110.8(3)
H7AA C7A H7AB 108.1
C8A C7A H7AA 109.5
C8A C7A H7AB 109.5
C7A C8A H8AA 109.7
C7A C8A H8AB 109.7
H8AA C8A H8AB 108.2
C9A C8A C7A 109.8(3)
C9A C8A H8AA 109.7
C9A C8A H8AB 109.7
C8A C9A H9A 115.3
C10A C9A C8A 129.4(4)
C10A C9A H9A 115.3
C9A C10A C11A 124.1(4)
C9A C10A C22A 119.2(4)
C22A C10A C11A 116.7(4)
C12A C11A C10A 122.4(4)
C12A C11A C16A 118.0(4)
C16A C11A C10A 119.6(4)
C11A C12A H12A 119.5
C13A C12A C11A 121.1(4)
C13A C12A H12A 119.5
C12A C13A C23A 118.8(4)
C14A C13A C12A 120.3(4)
C14A C13A C23A 120.9(4)
C13A C14A H14A 120.3
C13A C14A C15A 119.4(4)
C15A C14A H14A 120.3
C14A C15A H15A 119.6
C16A C15A C14A 120.7(4)
C16A C15A H15A 119.6
C11A C16A S1A 122.1(4)
C15A C16A S1A 117.5(3)
C15A C16A C11A 120.4(4)
C18A C17A S1A 118.0(4)
C18A C17A C22A 121.6(5)
C22A C17A S1A 120.4(4)
C17A C18A H18A 119.6
C17A C18A C19A 120.8(5)
C19A C18A H18A 119.6
C18A C19A H19A 120.7
C18A C19A C20A 118.5(5)
C20A C19A H19A 120.7
C19A C20A H20A 119.5
C21A C20A C19A 120.9(5)
C21A C20A H20A 119.5
C20A C21A H21A 119.3
C20A C21A C22A 121.4(5)
C22A C21A H21A 119.3
C17A C22A C10A 121.5(4)
C17A C22A C21A 116.5(4)
C21A C22A C10A 121.9(4)
F1A C23A F3A 106.4(11)
F1A C23A C13A 110.3(8)
F1AB C23A F2AB 82(5)
F1AB C23A F3AB 105(4)
F1AB C23A C13A 117.8(14)
F2A C23A F1A 105.5(12)
F2A C23A F3A 109.1(9)
F2A C23A C13A 114.9(4)
F2AB C23A C13A 115.7(12)
F3A C23A C13A 110.3(6)
F3AB C23A F2AB 109(3)
F3AB C23A C13A 120.3(11)
C2B O3B H3B 109.5
C3B O4B H4B 109.5
C4B O6B H6B 109.5
O1B C1B O2B 126.8(3)
O1B C1B C2B 116.5(3)
O2B C1B C2B 116.7(3)
O3B C2B C1B 110.4(3)
O3B C2B H2B 109.3
O3B C2B C3B 110.3(3)
C1B C2B H2B 109.3
C3B C2B C1B 108.4(3)
C3B C2B H2B 109.3
O4B C3B C2B 110.8(3)
O4B C3B H3BA 108.3
O4B C3B C4B 110.7(3)
C2B C3B H3BA 108.3
C4B C3B C2B 110.4(3)
C4B C3B H3BA 108.3
O5B C4B O6B 125.0(3)
O5B C4B C3B 122.7(3)
O6B C4B C3B 112.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1A C16A 1.754(5)
S1A C17A 1.788(5)
F1A C23A 1.311(12)
F1AB F2AB 1.71(8)
F1AB C23A 1.24(2)
F2A C23A 1.278(8)
F2AB C23A 1.37(3)
F3A C23A 1.314(8)
F3AB C23A 1.25(2)
O1A H1A 0.8200
O1A C6A 1.415(4)
N1A C1A 1.474(4)
N1A C4A 1.479(4)
N1A C7A 1.470(4)
N2A H2A 0.96(4)
N2A C2A 1.495(4)
N2A C3A 1.497(4)
N2A C5A 1.505(4)
C1A H1AA 0.9700
C1A H1AB 0.9700
C1A C2A 1.512(5)
C2A H2AA 0.9700
C2A H2AB 0.9700
C3A H3AA 0.9700
C3A H3AB 0.9700
C3A C4A 1.503(5)
C4A H4AA 0.9700
C4A H4AB 0.9700
C5A H5AA 0.9700
C5A H5AB 0.9700
C5A C6A 1.524(5)
C6A H6AA 0.9700
C6A H6AB 0.9700
C7A H7AA 0.9700
C7A H7AB 0.9700
C7A C8A 1.549(6)
C8A H8AA 0.9700
C8A H8AB 0.9700
C8A C9A 1.474(6)
C9A H9A 0.9300
C9A C10A 1.340(6)
C10A C11A 1.489(6)
C10A C22A 1.461(6)
C11A C12A 1.401(6)
C11A C16A 1.406(6)
C12A H12A 0.9300
C12A C13A 1.387(6)
C13A C14A 1.382(6)
C13A C23A 1.497(7)
C14A H14A 0.9300
C14A C15A 1.391(7)
C15A H15A 0.9300
C15A C16A 1.384(6)
C17A C18A 1.369(7)
C17A C22A 1.395(6)
C18A H18A 0.9300
C18A C19A 1.385(8)
C19A H19A 0.9300
C19A C20A 1.391(8)
C20A H20A 0.9300
C20A C21A 1.356(6)
C21A H21A 0.9300
C21A C22A 1.421(6)
O1B C1B 1.239(4)
O2B C1B 1.261(4)
O3B H3B 0.8200
O3B C2B 1.419(4)
O4B H4B 0.8200
O4B C3B 1.407(4)
O5B C4B 1.208(4)
O6B H6B 0.8200
O6B C4B 1.312(4)
C1B C2B 1.537(4)
C2B H2B 0.9800
C2B C3B 1.535(5)
C3B H3BA 0.9800
C3B C4B 1.526(4)
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
O1A H1A O1B 1_455 0.82 1.83 2.652(4) 178
N2A H2A O2B 1_455 0.96(4) 1.73(4) 2.675(3) 165(3)
O3B H3B O5B 3_656 0.82 2.18 2.903(3) 147
O4B H4B O3B 3_656 0.82 2.14 2.954(4) 175
O6B H6B N1A . 0.82 1.83 2.629(4) 165
C3A H3AB O5B . 0.97 2.59 3.314(4) 132
C5A H5AA O2B 3_666 0.97 2.53 3.466(4) 163
C15A H15A O1A 4_665 0.93 2.58 3.397(5) 148
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
S1A C17A C18A C19A -179.8(4)
S1A C17A C22A C10A 6.3(5)
S1A C17A C22A C21A -177.6(3)
F1AB F2AB C23A F1A -22(3)
F1AB F2AB C23A F2A 138(3)
F1AB F2AB C23A F3A 51(4)
F1AB F2AB C23A F3AB 104(4)
F1AB F2AB C23A C13A -117(3)
F2AB F1AB C23A F1A 27(3)
F2AB F1AB C23A F2A -43(4)
F2AB F1AB C23A F3A -142.6(18)
F2AB F1AB C23A F3AB -108(3)
F2AB F1AB C23A C13A 115(3)
N1A C1A C2A N2A -58.7(3)
N1A C7A C8A C9A 169.7(3)
N2A C3A C4A N1A 57.1(3)
N2A C5A C6A O1A -80.8(4)
C1A N1A C4A C3A -61.0(3)
C1A N1A C7A C8A 158.2(3)
C2A N2A C3A C4A -51.9(3)
C2A N2A C5A C6A 165.7(3)
C3A N2A C2A C1A 53.0(3)
C3A N2A C5A C6A -72.3(3)
C4A N1A C1A C2A 61.3(3)
C4A N1A C7A C8A -80.9(4)
C5A N2A C2A C1A 176.0(3)
C5A N2A C3A C4A -173.2(3)
C7A N1A C1A C2A -175.7(3)
C7A N1A C4A C3A 176.8(3)
C7A C8A C9A C10A 135.7(5)
C8A C9A C10A C11A 2.8(8)
C8A C9A C10A C22A -174.6(4)
C9A C10A C11A C12A 40.8(6)
C9A C10A C11A C16A -139.0(4)
C9A C10A C22A C17A 136.5(4)
C9A C10A C22A C21A -39.4(6)
C10A C11A C12A C13A -178.1(4)
C10A C11A C16A S1A -1.6(5)
C10A C11A C16A C15A 176.7(4)
C11A C10A C22A C17A -41.1(6)
C11A C10A C22A C21A 143.0(4)
C11A C12A C13A C14A -1.1(6)
C11A C12A C13A C23A -179.6(4)
C12A C11A C16A S1A 178.5(3)
C12A C11A C16A C15A -3.1(6)
C12A C13A C14A C15A 1.7(7)
C12A C13A C23A F1A -141.2(14)
C12A C13A C23A F1AB 178(6)
C12A C13A C23A F2A -22.2(10)
C12A C13A C23A F2AB -88(4)
C12A C13A C23A F3A 101.6(10)
C12A C13A C23A F3AB 47(4)
C13A C14A C15A C16A -3.1(7)
C14A C13A C23A F1A 40.3(14)
C14A C13A C23A F1AB -1(6)
C14A C13A C23A F2A 159.3(8)
C14A C13A C23A F2AB 94(4)
C14A C13A C23A F3A -77.0(10)
C14A C13A C23A F3AB -132(4)
C14A C15A C16A S1A -177.8(4)
C14A C15A C16A C11A 3.8(7)
C16A S1A C17A C18A -157.3(3)
C16A S1A C17A C22A 24.3(4)
C16A C11A C12A C13A 1.8(6)
C17A S1A C16A C11A -26.5(4)
C17A S1A C16A C15A 155.1(4)
C17A C18A C19A C20A -1.9(7)
C18A C17A C22A C10A -172.0(4)
C18A C17A C22A C21A 4.1(6)
C18A C19A C20A C21A 2.5(7)
C19A C20A C21A C22A 0.3(7)
C20A C21A C22A C10A 172.6(4)
C20A C21A C22A C17A -3.5(6)
C22A C10A C11A C12A -141.7(4)
C22A C10A C11A C16A 38.5(5)
C22A C17A C18A C19A -1.5(7)
C23A C13A C14A C15A -179.8(4)
O1B C1B C2B O3B 8.5(4)
O1B C1B C2B C3B -112.4(3)
O2B C1B C2B O3B -171.3(3)
O2B C1B C2B C3B 67.8(4)
O3B C2B C3B O4B -65.3(3)
O3B C2B C3B C4B 57.7(4)
O4B C3B C4B O5B 4.4(5)
O4B C3B C4B O6B -178.0(3)
C1B C2B C3B O4B 55.6(3)
C1B C2B C3B C4B 178.6(3)
C2B C3B C4B O5B -118.7(4)
C2B C3B C4B O6B 58.9(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139086308