Evaluating a Crystal Energy Landscape in the Context of Industrial Polymorph Screening
Ismail, Salima Z.; Anderton, Clare L.; Copley, Royston C. B.; Price, Louise S.; Price, Sarah L.; Crystal Growth & Design 13 (2013) 2396–; doi:10.1021/cg400090r

data_4507812
_publ_section_title
;
 Evaluating a Crystal Energy Landscape in the Context of Industrial
 Polymorph Screening
;
_journal_issue                   6
_journal_name_full               'Crystal Growth &amp; 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       \w
_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/[\s^2^(Fo^2^)+(0.0452P)^2^+0.4024P] where P=(Fo^2^+2Fc^2^)/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)'