Crystal Structure Analysis, Stability, Phase Transformation and Selective Nucleation Mechanism of Fluralaner Polymorphs
Li, Guangyan; Wang, Ting; Huang, Xin; Wang, Na; Zhou, Lina; Tian, Beiqian; Feng, Ziwei; Liu, Ailing; Li, Yaling; Hao, Hongxun; Crystals 13 (2023) 1241–; doi:10.3390/cryst13081241

data_1569810
_publ_section_title
;
 Crystal Structure Analysis, Stability, Phase Transformation and Selective
 Nucleation Mechanism of Fluralaner Polymorphs
;
_journal_issue                   8
_journal_name_full               Crystals
_journal_page_first              1241
_journal_paper_doi               10.3390/cryst13081241
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C22 H17 Cl2 F6 N3 O3'
_chemical_formula_sum            'C22 H17 Cl2 F6 N3 O3'
_chemical_formula_weight         556.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                72.469(2)
_cell_angle_beta                 83.305(2)
_cell_angle_gamma                89.077(2)
_cell_formula_units_Z            4
_cell_length_a                   9.5129(3)
_cell_length_b                   15.1300(3)
_cell_length_c                   17.6150(5)
_cell_measurement_reflns_used    18012
_cell_measurement_temperature    295(9)
_cell_measurement_theta_max      75.4530
_cell_measurement_theta_min      2.6290
_cell_volume                     2400.60(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295(9)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -81.00 -56.00   0.50    0.14    --  -39.45 118.00-161.00   50
  2  \w   -112.00 -67.00   0.50    0.14    --  -39.45-158.00 -41.00   90
  3  \w    -90.00 -65.00   0.50    0.14    --  -39.45 158.00  -7.00   50
  4  \w     77.00 114.00   0.50    0.14    --   39.45-158.00 -41.00   74
  5  \w     14.00  74.00   0.50    0.14    --   39.45-118.00 112.00  120
  6  \w     55.00 110.00   0.50    0.14    --   39.45 158.00  -7.00  110
  7  \w   -108.00 -20.00   0.50    0.58    --  -52.00 118.00-161.00  176
  8  \w   -117.00 -92.00   0.50    0.58    --  -52.00-158.00 -41.00   50
  9  \w   -109.00 -84.00   0.50    0.58    --  -52.00 158.00  -7.00   50
 10  \w     79.00 104.00   0.50    0.58    --  111.82-118.00 112.00   50
 11  \w    112.00 138.00   0.50    0.58    --  111.82 118.00-161.00   52
 12  \w     38.00  64.00   0.50    0.58    --  111.82-158.00 -41.00   52
 13  \w    114.00 160.00   0.50    0.58    --  111.82 158.00  -7.00   92
 14  \w    -46.00 -13.00   0.50    0.14    --  -39.45 -57.00-120.00   66
 15  \w   -115.00 -57.00   0.50    0.14    --  -39.45 -57.00-120.00  116
 16  \w   -115.00 -21.00   0.50    0.14    --  -39.45 -57.00  30.00  188
 17  \w   -114.00  -5.00   0.50    0.14    --  -39.45 -77.00 150.00  218
 18  \w   -113.00 -63.00   0.50    0.14    --  -39.45 -77.00 -90.00  100
 19  \w    -38.00  -5.00   0.50    0.14    --  -39.45 -77.00 -90.00   66
 20  \w      7.00  85.00   0.50    0.14    --   39.45  37.00  30.00  156
 21  \w    -41.00 -15.00   0.50    0.58    --  -52.00 -83.00  36.02   52
 22  \w    -41.00 -13.00   0.50    0.58    --  -52.00 -87.00 134.01   56
 23  \w    -37.00 -12.00   0.50    0.58    --  -52.00 -88.00-126.40   50
 24  \w    -38.00  30.00   0.50    0.58    --  -52.00  30.00   0.00  136
 25  \w    -40.00 -14.00   0.50    0.58    --  -52.00 -85.00 -29.43   52
 26  \w     21.00  53.00   0.50    0.14    --   56.00  77.00-105.70   64
 27  \w     25.00  51.00   0.50    0.14    --   60.00  78.00 -67.11   52
 28  \w     25.00  67.00   0.50    0.14    --   60.00  77.00-162.96   84
 29  \w     29.00  79.00   0.50    0.14    --   64.00  78.00  37.43  100
 30  \w     29.00  79.00   0.50    0.14    --   64.00  78.00 -45.77  100
 31  \w     90.00 139.00   0.50    0.14    --   64.00  78.00 -45.77   98
 32  \w     98.00 137.00   0.50    0.14    --   64.00  78.00  37.43   78
 33  \w    103.00 129.00   0.50    0.14    --   68.00  69.00 129.14   52
 34  \w     33.00  62.00   0.50    0.14    --   68.00  78.00 -19.13   58
 35  \w     81.00 143.00   0.50    0.14    --   68.00  74.00  82.82  124
 36  \w     36.00  76.00   0.50    0.14    --   68.00  71.00-122.32   80
 37  \w     35.00  72.00   0.50    0.14    --   68.00  74.00  82.82   74
 38  \w     37.00  69.00   0.50    0.14    --   68.00  69.00 129.14   64
 39  \w     37.00  62.00   0.50    0.14    --   72.00  78.00 138.44   50
 40  \w     50.00  80.00   0.50    0.58    --   80.00  64.00  21.06   60
 41  \w     97.00 123.00   0.50    0.58    --   80.00  64.00  21.06   52
 42  \w    106.00 155.00   0.50    0.58    --   80.00  78.00 141.41   98
 43  \w     45.00  76.00   0.50    0.58    --   80.00  78.00 141.41   62
 44  \w    110.00 159.00   0.50    0.58    --   84.00  62.00-169.91   98
 45  \w     55.00 101.00   0.50    0.58    --   84.00  62.00-169.91   92
 46  \w    127.00 165.00   0.50    0.58    --   92.00  75.00 -78.40   76
 47  \w     58.00 121.00   0.50    0.58    --   92.00  75.00 -78.40  126
 48  \w    113.00 142.00   0.50    0.58    --  111.82  77.00 150.00   58
 49  \w     83.00 109.00   0.50    0.58    --  111.82  61.00  30.00   52
 50  \w     77.00 108.00   0.50    0.58    --  111.82  77.00 150.00   62
 51  \w    114.00 169.00   0.50    0.58    --  111.82  77.00 -60.00  110
 52  \w     83.00 156.00   0.50    0.58    --  111.82  61.00-180.00  146
 53  \w     77.00 105.00   0.50    0.58    --  111.82  77.00 -60.00   56
 54  \w     83.00 168.00   0.50    0.58    --  111.82  61.00 120.00  170
 55  \w    120.00 169.00   0.50    0.58    --  111.82  77.00  60.00   98
 56  \w     77.00 113.00   0.50    0.58    --  111.82  77.00  60.00   72
 57  \w     38.00  98.00   0.50    0.58    --  111.82 -77.00 150.00  120
 58  \w     77.00 105.00   0.50    0.58    --  111.82  77.00 -30.00   56
 59  \w     81.00 108.00   0.50    0.58    --  111.82-111.00 150.00   54
 60  \w    130.00 175.00   0.50    0.58    --  111.82  77.00   0.00   90
 61  \w     77.00 105.00   0.50    0.58    --  111.82 -94.00 -60.00   56
 62  \w    112.00 169.00   0.50    0.58    --  111.82  77.00 -30.00  114
 63  \w     36.00  76.00   0.50    0.58    --  111.82-111.00 150.00   80
 64  \w    128.00 168.00   0.50    0.58    --  111.82  77.00  90.00   80
 65  \w     77.00 103.00   0.50    0.58    --  111.82  77.00   0.00   52
 66  \w     77.00 104.00   0.50    0.58    --  111.82  77.00 120.00   54
 67  \w    106.00 131.00   0.50    0.58    --  111.82  77.00 120.00   50
 68  \w     77.00 109.00   0.50    0.58    --  111.82  77.00  90.00   64
 69  \w     38.00  70.00   0.50    0.58    --  111.82 -94.00 -60.00   64
 70  \w     83.00 111.00   0.50    0.58    --  111.82  61.00-150.00   56
 71  \w    117.00 152.00   0.50    0.58    --  111.82  61.00-150.00   70
 72  \w     77.00 131.00   0.50    0.58    --  111.82  77.00  30.00  108
 73  \w    115.00 174.00   0.50    0.58    --  111.82  61.00  30.00  118
 74  \w     32.00 108.00   0.50    0.58    --  111.82-111.00-120.00  152
 75  \w     77.00 175.00   0.50    0.58    --  111.82  77.00-150.00  196
 76  \w     78.00 103.00   0.50    0.58    --  111.82 -94.00  30.00   50
 77  \w     85.00 168.00   0.50    0.58    --  111.82  61.00 150.00  166
 78  \w     83.00 150.00   0.50    0.58    --  111.82  61.00  90.00  134
 79  \w     32.00  70.00   0.50    0.58    --  111.82 -94.00  30.00   76
 80  \w    133.00 175.00   0.50    0.58    --  111.82  77.00-180.00   84
 81  \w     33.00 107.00   0.50    0.58    --  111.82-111.00 -60.00  148
 82  \w    113.00 149.00   0.50    0.58    --  111.82  61.00  60.00   72
 83  \w     77.00 103.00   0.50    0.58    --  111.82  77.00-180.00   52
 84  \w     85.00 111.00   0.50    0.58    --  111.82  61.00 -60.00   52
 85  \w     85.00 172.00   0.50    0.58    --  111.82  61.00 -90.00  174
 86  \w     83.00 109.00   0.50    0.58    --  111.82  61.00  60.00   52
 87  \w     38.00  96.00   0.50    0.58    --  111.82 -77.00 -60.00  116
 88  \w    117.00 150.00   0.50    0.58    --  111.82  61.00 -60.00   66
 89  \w     83.00 149.00   0.50    0.58    --  111.82  61.00   0.00  132
 90  \w     69.00  99.00   0.50    0.58    --  111.82 -94.00   0.00   60
 91  \w     42.00  67.00   0.50    0.58    --  111.82 -61.00 120.00   50
 92  \w     45.00  93.00   0.50    0.58    --  111.82 -77.00  30.00   96
 93  \w     77.00 150.00   0.50    0.58    --  111.82  77.00-120.00  146
 94  \w     32.00  57.00   0.50    0.58    --  111.82 -94.00   0.00   50
 95  \w     83.00 170.00   0.50    0.58    --  111.82  61.00 -30.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0491555000
_diffrn_orient_matrix_UB_12      -0.0660818000
_diffrn_orient_matrix_UB_13      0.0840801000
_diffrn_orient_matrix_UB_21      -0.0080694000
_diffrn_orient_matrix_UB_22      -0.0807306000
_diffrn_orient_matrix_UB_23      -0.0357846000
_diffrn_orient_matrix_UB_31      0.1552964000
_diffrn_orient_matrix_UB_32      -0.0228593000
_diffrn_orient_matrix_UB_33      0.0133882000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            46081
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.073
_diffrn_reflns_theta_min         2.649
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.810
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         9081
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.207
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0946
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2623
_refine_ls_wR_factor_ref         0.3136
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6424
_reflns_number_total             9081
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            EBLS-300K_auto.cif
_cod_data_source_block           ebls-300k_auto
_cod_original_cell_volume        2400.61(12)
_cod_database_code               1569810
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.685
_shelx_estimated_absorpt_t_min   0.572
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N3-H3 = N2-H2 = N3A-H3A = N2A-H2AA
 0.9 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C19(H19A,H19B), C21(H21A,H21B), C9A(H9AA,H9AB), C19A(H19C,H19D),
 C21A(H21C,H21D)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C6(H6), C12(H12), C15(H15), C16(H16), C2A(H2AB), C4A(H4A),
 C6A(H6A), C12A(H12A), C15A(H15A), C16A(H16A)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C17A(H17D,H17E,H17F)
;
_shelx_res_checksum              52085
_shelx_hkl_checksum              40686
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.621
_oxdiff_exptl_absorpt_empirical_full_min 0.519