#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/78/4507812.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_4507812
loop_
_publ_author_name
'Ismail, Salima Z.'
'Anderton, Clare L.'
'Copley, Royston C. B.'
'Price, Louise S.'
'Price, Sarah L.'
_publ_section_title
;
 Evaluating a Crystal Energy Landscape in the Context of Industrial
 Polymorph Screening
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2396
_journal_paper_doi               10.1021/cg400090r
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C20 H14 Cl2 F N O3, 2(C2 H6 O S)'
_chemical_formula_sum            'C24 H26 Cl2 F N O5 S2'
_chemical_formula_weight         562.48
_chemical_name_systematic
;
6-[(5-Chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)methyl]-
2-pyridinecarboxylic acid, DMSO solvate (1:2)
;
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_cell_angle_alpha                116.333(3)
_cell_angle_beta                 91.503(2)
_cell_angle_gamma                105.955(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2693(2)
_cell_length_b                   13.0633(4)
_cell_length_c                   14.2559(4)
_cell_measurement_reflns_used    28191
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      75.5200
_cell_measurement_theta_min      3.5087
_cell_volume                     1307.25(8)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_molecular_graphics    'SHELXTL XP V5.10 XP (Bruker, 1998)'
_computing_publication_material  'SHELXTL XCIF V6.12 XP (Bruker, 2001)'
_computing_structure_refinement  'SHELXTL XL V6.12 XP (Bruker, 2001)'
_computing_structure_solution    'SHELXTL XS V6.12 XP (Bruker, 2001)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.2872
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega  -98.00   -2.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.1425  125.0000  -42.0000 96

  2 omega   17.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       42.1425   38.0000 -120.0000 98

  3 omega  -35.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       42.1425  -77.0000  150.0000 110

  4 omega   46.00   73.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       42.1425   77.0000  -30.0000 27

  5 omega   24.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       42.1425   38.0000  -30.0000 45

  6 omega    8.00   34.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       42.1425   77.0000  -30.0000 26

  7 omega   21.00  118.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       42.1425   38.0000  120.0000 97

  8 omega    6.00   32.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   90.0000   94.0000 26

  9 omega   13.00   39.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   82.0000    7.0000 26

 10 omega   12.00   37.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   84.0000  175.0000 25

 11 omega   17.00   42.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   82.0000  125.0000 25

 12 omega  -56.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -62.0000  -77.0000  -98.0000 28

 13 omega   32.00   58.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  -50.0000 26

 14 omega   30.00   55.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000 -140.0000 25

 15 omega -138.00 -112.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -66.0000  -77.0000 -135.0000 26

 16 omega  -65.00  -32.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -66.0000  -77.0000 -135.0000 33

 17 omega   32.00   58.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000 -175.0000 26

 18 omega  120.00  145.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000 -127.0000 25

 19 omega   33.00   59.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000   21.0000 26

 20 omega   32.00   61.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000 -127.0000 29

 21 omega  -75.00  -37.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000  -77.0000   39.0000 38

 22 omega  -63.00  -37.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000  -77.0000  -10.0000 26

 23 omega  -71.00  -42.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -69.0000 -162.0000 29

 24 omega -134.00 -108.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -69.0000 -162.0000 26

 25 omega  -79.00  -44.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -71.0000  146.0000 35

 26 omega -150.00 -117.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -71.0000  146.0000 33

 27 omega -104.00  -45.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -76.0000  -71.0000  133.0000 59

 28 omega  -68.00  -43.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -76.0000  -73.0000  109.0000 25

 29 omega -151.00 -117.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -76.0000  -73.0000  109.0000 34

 30 omega -147.00 -122.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -78.0000  -67.0000  -80.0000 25

 31 omega  -70.00  -45.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -78.0000  -73.0000   85.0000 25

 32 omega  -81.00  -49.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -78.0000  -67.0000  -80.0000 32

 33 omega  -74.00  -48.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -80.0000  -71.0000   57.0000 26

 34 omega -101.00  -52.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -84.0000  -69.0000   12.0000 49

 35 omega -158.00 -130.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -84.0000  -65.0000  -41.0000 28

 36 omega  -81.00  -56.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -84.0000  -66.0000  168.0000 25

 37 omega  -79.00  -54.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -84.0000  -65.0000  -41.0000 25

 38 omega  -82.00  -57.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -75.0000  101.0000 25

 39 omega -153.00 -127.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -75.0000  101.0000 26

 40 omega  -83.00  -57.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -91.0000  -77.0000  -72.0000 26

 41 omega  -86.00  -60.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -91.0000  -69.0000   84.0000 26

 42 omega  -83.00  -57.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -91.0000  -77.0000 -105.0000 26

 43 omega  -87.00  -61.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -91.0000  -68.0000  112.0000 26

 44 omega  -83.00  -57.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -91.0000  -77.0000   30.0000 26

 45 omega  -83.00  -57.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -91.0000  -77.0000  -30.0000 26

 46 omega  -82.00  -57.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -91.0000  -77.0000 -150.0000 25

 47 omega  -83.00  -57.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -91.0000  -77.0000    0.0000 26

 48 omega  -85.00  -59.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -91.0000  -77.0000  150.0000 26

 49 omega  -83.00  -57.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -91.0000  -77.0000   60.0000 26

 50 omega  -84.00  -58.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -91.0000  -77.0000 -180.0000 26

 51 omega  -82.00  -57.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -91.0000  -77.0000 -120.0000 25

 52 omega  -86.00  -61.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -91.0000  -71.0000  154.0000 25

 53 omega  -85.00  -59.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -91.0000  -75.0000   71.0000 26

 54 omega   77.00  174.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  120.0000 97

 55 omega   79.00  132.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  -30.0000 53

 56 omega   77.00  173.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000 -180.0000 96

 57 omega   77.00  171.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000   90.0000 94

 58 omega  122.00  166.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000 -150.0000 44

 59 omega   83.00  109.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000 -150.0000 26

 60 omega  120.00  172.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000    0.0000 52

 61 omega   77.00  102.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000    0.0000 25

 62 omega  109.00  164.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  -90.0000 55

 63 omega   80.00  106.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  -90.0000 26

 64 omega  115.00  141.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000   60.0000 26

 65 omega   38.00  103.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -15.0000 -180.0000 65

 66 omega   78.00  104.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000   60.0000 26

 67 omega   92.00  118.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000  -90.0000 26

 68 omega  109.00  135.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -149.0000   57.0000 26

 69 omega   33.00   65.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000  -90.0000 32

 70 omega  143.00  168.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  111.0000 -180.0000 25

 71 omega   53.00   88.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -149.0000   57.0000 35

 72 omega  123.00  156.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  -60.0000 33

 73 omega   49.00   74.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000   90.0000 25

 74 omega   78.00  106.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  -60.0000 28

 75 omega   77.00  104.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000   30.0000 27

 76 omega   61.00  141.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000   90.0000 80

 77 omega  135.00  177.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000 -120.0000 42

 78 omega   78.00  119.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000 -120.0000 41

 79 omega  115.00  141.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000 -150.0000 26

 80 omega  118.00  145.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000 -120.0000 27

 81 omega   67.00  109.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000 -150.0000 42

 82 omega   41.00   78.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000 -120.0000 37

 83 omega  108.00  135.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -149.0000 -105.0000 27

 84 omega  142.00  167.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000  -30.0000 25

 85 omega   99.00  128.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000  -30.0000 29

 86 omega   37.00   63.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -149.0000 -105.0000 26

 87 omega   92.00  144.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  179.0000 -180.0000 52

 88 omega   34.00   68.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  179.0000 -180.0000 34

 89 omega   32.00   97.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000 -150.0000 65

 90 omega   87.00  149.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  179.0000   30.0000 62

 91 omega   41.00   77.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  120.0000 36

 92 omega   83.00  142.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000   30.0000 59

 93 omega   87.00  146.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000   60.0000 59

 94 omega  104.00  130.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  111.0000 -180.0000 26

 95 omega   83.00  154.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000 -120.0000 71

 96 omega   60.00  120.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -121.0000   59.0000 60

 97 omega  110.00  149.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  179.0000 -120.0000 39

 98 omega   93.00  120.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000 -120.0000 27

 99 omega   46.00   73.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000 -120.0000 27

100 omega  109.00  134.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -15.0000 -180.0000 25

101 omega   90.00  142.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000   90.0000 52

102 omega   88.00  150.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  179.0000   60.0000 62

103 omega   77.00  173.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  150.0000 96
;
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur A Nova'
_diffrn_measurement_method       ω
_diffrn_orient_matrix_UB_11      0.0471365000
_diffrn_orient_matrix_UB_12      0.1114847000
_diffrn_orient_matrix_UB_13      -0.0183778000
_diffrn_orient_matrix_UB_21      -0.0259513000
_diffrn_orient_matrix_UB_22      -0.0825125000
_diffrn_orient_matrix_UB_23      -0.1206053000
_diffrn_orient_matrix_UB_31      -0.1891890000
_diffrn_orient_matrix_UB_32      -0.0070809000
_diffrn_orient_matrix_UB_33      -0.0099166000
_diffrn_radiation_collimation    '0.3 mm pinhole'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0092
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31014
_diffrn_reflns_theta_full        75.70
_diffrn_reflns_theta_max         75.70
_diffrn_reflns_theta_min         3.51
_exptl_absorpt_coefficient_mu    4.098
_exptl_absorpt_correction_T_max  0.778
_exptl_absorpt_correction_T_min  0.471
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     'SHELXTL XL V6.12 XP (Bruker, 2001)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0282
_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)+(0.0452P)²+0.4024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0796
_reflns_number_gt                5282
_reflns_number_total             5379
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400090r_si_002.cif
_cod_data_source_block           Form6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.3.1 from 2005-06-27 (35
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.3.1 from 2005-06-27 (46
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.3.1 from 2005-06-27 (49 times).

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1307.26(7)
_cod_database_code               4507812
_computing_data_merging          'SHELXTL XL V6.12 XP (Bruker, 2001)'
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
_atom_site_refinement_flags
Cl1 Cl 1.28805(5) 0.51466(4) 0.98213(3) 0.05515(12) Uani 1 1 d .
Cl2 Cl 0.40043(5) 0.38416(4) 0.18826(3) 0.04755(10) Uani 1 1 d .
F1 F 0.83244(11) 0.70294(7) 0.51353(7) 0.04044(19) Uani 1 1 d .
O1 O 0.85901(11) 0.45560(7) 0.61545(7) 0.03111(19) Uani 1 1 d .
O2 O 0.12456(11) 0.02659(8) 0.41394(7) 0.03302(19) Uani 1 1 d .
H1 H 0.071(3) -0.014(2) 0.3466(18) 0.064(6) Uiso 1 1 d .
O3 O 0.35177(12) 0.05711(10) 0.33690(8) 0.0435(2) Uani 1 1 d .
N1 N 0.56370(13) 0.16422(9) 0.52923(8) 0.0267(2) Uani 1 1 d .
C1 C 0.66330(16) 0.22121(10) 0.62456(10) 0.0280(2) Uani 1 1 d .
C2 C 0.59553(18) 0.24819(12) 0.71849(10) 0.0352(3) Uani 1 1 d .
H12 H 0.6691 0.2909 0.7854 0.042 Uiso 1 1 calc R
C3 C 0.42074(18) 0.21204(13) 0.71277(11) 0.0374(3) Uani 1 1 d .
H13 H 0.3726 0.2296 0.7757 0.045 Uiso 1 1 calc R
C4 C 0.31605(17) 0.14979(12) 0.61403(10) 0.0322(3) Uani 1 1 d .
H14 H 0.1954 0.1218 0.6075 0.039 Uiso 1 1 calc R
C5 C 0.39374(15) 0.12970(10) 0.52504(10) 0.0265(2) Uani 1 1 d .
C6 C 0.85360(16) 0.25086(11) 0.62476(11) 0.0313(3) Uani 1 1 d .
H10 H 0.8917 0.1890 0.6324 0.038 Uiso 1 1 calc R
H11 H 0.8754 0.2457 0.5551 0.038 Uiso 1 1 calc R
C7 C 0.96018(15) 0.37365(11) 0.71121(10) 0.0288(2) Uani 1 1 d .
C8 C 0.96187(15) 0.47758(11) 0.70385(9) 0.0273(2) Uani 1 1 d .
C9 C 1.06293(16) 0.59123(11) 0.78052(10) 0.0302(2) Uani 1 1 d .
H4 H 1.0635 0.6606 0.7741 0.036 Uiso 1 1 calc R
C10 C 1.16363(17) 0.60308(12) 0.86705(10) 0.0343(3) Uani 1 1 d .
H3 H 1.2332 0.6804 0.9200 0.041 Uiso 1 1 calc R
C11 C 1.16083(17) 0.50109(13) 0.87470(11) 0.0362(3) Uani 1 1 d .
C12 C 1.06130(17) 0.38679(12) 0.79757(11) 0.0336(3) Uani 1 1 d .
H2 H 1.0626 0.3177 0.8041 0.040 Uiso 1 1 calc R
C13 C 0.86365(15) 0.55496(10) 0.59773(9) 0.0263(2) Uani 1 1 d .
H5 H 0.9810 0.5943 0.5920 0.032 Uiso 1 1 calc R
H6 H 0.8277 0.6151 0.6576 0.032 Uiso 1 1 calc R
C14 C 0.74379(14) 0.50776(10) 0.49607(9) 0.0247(2) Uani 1 1 d .
C15 C 0.73381(16) 0.58562(11) 0.45620(10) 0.0287(2) Uani 1 1 d .
C16 C 0.63093(17) 0.55163(12) 0.36327(11) 0.0333(3) Uani 1 1 d .
H7 H 0.6284 0.6079 0.3385 0.040 Uiso 1 1 calc R
C17 C 0.53102(16) 0.43164(12) 0.30726(10) 0.0312(3) Uani 1 1 d .
C18 C 0.53278(16) 0.35001(11) 0.34368(10) 0.0313(3) Uani 1 1 d .
H8 H 0.4619 0.2684 0.3047 0.038 Uiso 1 1 calc R
C19 C 0.63914(15) 0.38828(11) 0.43788(10) 0.0277(2) Uani 1 1 d .
H9 H 0.6406 0.3322 0.4631 0.033 Uiso 1 1 calc R
C20 C 0.29022(15) 0.06791(10) 0.41563(10) 0.0282(2) Uani 1 1 d .
S1 S 0.07034(4) -0.11218(3) 0.13334(2) 0.03115(9) Uani 1 1 d .
O4 O -0.04120(11) -0.10144(8) 0.21840(7) 0.0342(2) Uani 1 1 d .
C21 C -0.07621(18) -0.19939(13) 0.01098(11) 0.0398(3) Uani 1 1 d .
H15 H -0.1287 -0.2815 0.0007 0.060 Uiso 1 1 calc R
H16 H -0.0153 -0.2022 -0.0477 0.060 Uiso 1 1 calc R
H17 H -0.1652 -0.1625 0.0127 0.060 Uiso 1 1 calc R
C22 C 0.12843(18) 0.02922(13) 0.13225(11) 0.0376(3) Uani 1 1 d .
H18 H 0.0255 0.0505 0.1255 0.056 Uiso 1 1 calc R
H19 H 0.1869 0.0234 0.0720 0.056 Uiso 1 1 calc R
H20 H 0.2049 0.0915 0.1987 0.056 Uiso 1 1 calc R
S2 S 0.63012(4) 0.08270(3) 0.16941(3) 0.03331(9) Uani 1 1 d .
O5 O 0.75962(13) 0.09556(9) 0.09956(8) 0.0423(2) Uani 1 1 d .
C23 C 0.52595(19) -0.07516(13) 0.11788(12) 0.0407(3) Uani 1 1 d .
H21 H 0.4611 -0.1079 0.0467 0.061 Uiso 1 1 calc R
H22 H 0.4480 -0.0889 0.1648 0.061 Uiso 1 1 calc R
H23 H 0.6115 -0.1154 0.1138 0.061 Uiso 1 1 calc R
C24 C 0.74549(18) 0.10970(14) 0.29022(11) 0.0392(3) Uani 1 1 d .
H24 H 0.8125 0.0544 0.2742 0.059 Uiso 1 1 calc R
H25 H 0.6650 0.0964 0.3361 0.059 Uiso 1 1 calc R
H26 H 0.8223 0.1931 0.3267 0.059 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 0.0181 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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -1.00 0.00 0.105
-1.00 1.00 0.00 0.105
0.00 -1.00 0.00 0.070
0.00 1.00 0.00 0.070
0.00 0.00 -1.00 0.035
0.00 0.00 1.00 0.035
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C8 O1 C13 117.82(9) y
C20 O2 H1 108.9(14) ?
C1 N1 C5 117.95(10) y
N1 C1 C2 122.01(12) y
N1 C1 C6 116.04(11) y
C2 C1 C6 121.91(11) y
C3 C2 C1 119.27(12) y
C3 C2 H12 120.4 ?
C1 C2 H12 120.4 ?
C2 C3 C4 119.24(12) y
C2 C3 H13 120.4 ?
C4 C3 H13 120.4 ?
C3 C4 C5 117.74(12) y
C3 C4 H14 121.1 ?
C5 C4 H14 121.1 ?
N1 C5 C4 123.74(11) y
N1 C5 C20 114.95(10) y
C4 C5 C20 121.31(11) y
C7 C6 C1 114.82(10) y
C7 C6 H10 108.6 ?
C1 C6 H10 108.6 ?
C7 C6 H11 108.6 ?
C1 C6 H11 108.6 ?
H10 C6 H11 107.5 ?
C12 C7 C8 118.49(11) y
C12 C7 C6 121.48(11) y
C8 C7 C6 120.00(11) y
O1 C8 C9 124.55(11) y
O1 C8 C7 114.31(10) y
C9 C8 C7 121.13(11) y
C8 C9 C10 119.74(12) y
C8 C9 H4 120.1 ?
C10 C9 H4 120.1 ?
C11 C10 C9 119.10(12) y
C11 C10 H3 120.4 ?
C9 C10 H3 120.4 ?
C10 C11 C12 121.48(12) y
C10 C11 Cl1 119.53(11) y
C12 C11 Cl1 118.98(11) y
C7 C12 C11 120.04(12) y
C7 C12 H2 120.0 ?
C11 C12 H2 120.0 ?
O1 C13 C14 107.69(9) y
O1 C13 H5 110.2 ?
C14 C13 H5 110.2 ?
O1 C13 H6 110.2 ?
C14 C13 H6 110.2 ?
H5 C13 H6 108.5 ?
C15 C14 C19 116.83(11) y
C15 C14 C13 119.38(10) y
C19 C14 C13 123.79(10) y
F1 C15 C16 118.50(11) y
F1 C15 C14 117.33(11) y
C16 C15 C14 124.17(11) y
C15 C16 C17 117.01(11) y
C15 C16 H7 121.5 ?
C17 C16 H7 121.5 ?
C18 C17 C16 121.65(12) y
C18 C17 Cl2 119.77(10) y
C16 C17 Cl2 118.59(10) y
C17 C18 C19 119.38(12) y
C17 C18 H8 120.3 ?
C19 C18 H8 120.3 ?
C18 C19 C14 120.95(11) y
C18 C19 H9 119.5 ?
C14 C19 H9 119.5 ?
O3 C20 O2 123.40(12) y
O3 C20 C5 123.56(11) y
O2 C20 C5 113.04(10) y
O4 S1 C21 104.54(6) y
O4 S1 C22 106.27(6) y
C21 S1 C22 98.15(7) y
S1 C21 H15 109.5 ?
S1 C21 H16 109.5 ?
H15 C21 H16 109.5 ?
S1 C21 H17 109.5 ?
H15 C21 H17 109.5 ?
H16 C21 H17 109.5 ?
S1 C22 H18 109.5 ?
S1 C22 H19 109.5 ?
H18 C22 H19 109.5 ?
S1 C22 H20 109.5 ?
H18 C22 H20 109.5 ?
H19 C22 H20 109.5 ?
O5 S2 C23 106.17(6) y
O5 S2 C24 106.79(6) y
C23 S2 C24 97.98(7) y
S2 C23 H21 109.5 ?
S2 C23 H22 109.5 ?
H21 C23 H22 109.5 ?
S2 C23 H23 109.5 ?
H21 C23 H23 109.5 ?
H22 C23 H23 109.5 ?
S2 C24 H24 109.5 ?
S2 C24 H25 109.5 ?
H24 C24 H25 109.5 ?
S2 C24 H26 109.5 ?
H24 C24 H26 109.5 ?
H25 C24 H26 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C11 1.7481(13) y
Cl2 C17 1.7409(13) y
F1 C15 1.3595(14) y
O1 C8 1.3720(14) y
O1 C13 1.4192(14) y
O2 C20 1.3224(15) y
O2 H1 0.89(2) ?
O3 C20 1.2115(16) y
N1 C1 1.3365(16) y
N1 C5 1.3436(16) y
C1 C2 1.4002(18) y
C1 C6 1.5133(17) y
C2 C3 1.380(2) y
C2 H12 0.9500 ?
C3 C4 1.3877(19) y
C3 H13 0.9500 ?
C4 C5 1.3897(17) y
C4 H14 0.9500 ?
C5 C20 1.5001(17) y
C6 C7 1.5102(17) y
C6 H10 0.9900 ?
C6 H11 0.9900 ?
C7 C12 1.3871(18) y
C7 C8 1.4037(17) y
C8 C9 1.3884(17) y
C9 C10 1.3946(18) y
C9 H4 0.9500 ?
C10 C11 1.378(2) y
C10 H3 0.9500 ?
C11 C12 1.392(2) y
C12 H2 0.9500 ?
C13 C14 1.5029(16) y
C13 H5 0.9900 ?
C13 H6 0.9900 ?
C14 C15 1.3861(16) y
C14 C19 1.3943(16) y
C15 C16 1.3738(18) y
C16 C17 1.3857(19) y
C16 H7 0.9500 ?
C17 C18 1.3807(19) y
C18 C19 1.3884(18) y
C18 H8 0.9500 ?
C19 H9 0.9500 ?
S1 O4 1.5230(9) y
S1 C21 1.7823(14) y
S1 C22 1.7836(14) y
C21 H15 0.9800 ?
C21 H16 0.9800 ?
C21 H17 0.9800 ?
C22 H18 0.9800 ?
C22 H19 0.9800 ?
C22 H20 0.9800 ?
S2 O5 1.5074(10) y
S2 C23 1.7834(14) y
S2 C24 1.7862(15) y
C23 H21 0.9800 ?
C23 H22 0.9800 ?
C23 H23 0.9800 ?
C24 H24 0.9800 ?
C24 H25 0.9800 ?
C24 H26 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H1 O4 0.89(2) 1.73(2) 2.6172(13) 176(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_publ_flag
C5 N1 C1 C2 -1.82(17) y
C5 N1 C1 C6 176.04(10) y
N1 C1 C2 C3 1.88(19) y
C6 C1 C2 C3 -175.85(12) y
C1 C2 C3 C4 0.0(2) y
C2 C3 C4 C5 -1.7(2) y
C1 N1 C5 C4 -0.08(17) y
C1 N1 C5 C20 179.16(10) y
C3 C4 C5 N1 1.85(19) y
C3 C4 C5 C20 -177.34(12) y
N1 C1 C6 C7 139.28(11) y
C2 C1 C6 C7 -42.86(16) y
C1 C6 C7 C12 107.91(13) y
C1 C6 C7 C8 -73.78(15) y
C13 O1 C8 C9 3.91(17) y
C13 O1 C8 C7 -175.16(10) y
C12 C7 C8 O1 179.53(11) y
C6 C7 C8 O1 1.17(16) y
C12 C7 C8 C9 0.42(18) y
C6 C7 C8 C9 -177.93(11) y
O1 C8 C9 C10 -179.60(11) y
C7 C8 C9 C10 -0.58(19) y
C8 C9 C10 C11 0.04(19) y
C9 C10 C11 C12 0.7(2) y
C9 C10 C11 Cl1 179.40(10) y
C8 C7 C12 C11 0.28(19) y
C6 C7 C12 C11 178.61(12) y
C10 C11 C12 C7 -0.8(2) y
Cl1 C11 C12 C7 -179.57(10) y
C8 O1 C13 C14 178.95(9) y
O1 C13 C14 C15 -175.28(10) y
O1 C13 C14 C19 4.91(15) y
C19 C14 C15 F1 178.55(10) y
C13 C14 C15 F1 -1.27(16) y
C19 C14 C15 C16 -1.30(18) y
C13 C14 C15 C16 178.87(11) y
F1 C15 C16 C17 -179.47(11) y
C14 C15 C16 C17 0.38(19) y
C15 C16 C17 C18 0.83(19) y
C15 C16 C17 Cl2 -179.29(9) y
C16 C17 C18 C19 -1.04(19) y
Cl2 C17 C18 C19 179.08(9) y
C17 C18 C19 C14 0.06(18) y
C15 C14 C19 C18 1.05(17) y
C13 C14 C19 C18 -179.13(11) y
N1 C5 C20 O3 -5.41(18) y
C4 C5 C20 O3 173.85(12) y
N1 C5 C20 O2 174.74(10) y
C4 C5 C20 O2 -6.00(16) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652554
