A Prolific Solvate Former, Galunisertib, under the Pressure of Crystal Structure Prediction, Produces Ten Diverse Polymorphs.
Bhardwaj, Rajni M.; McMahon, Jennifer A.; Nyman, Jonas; Price, Louise S.; Konar, Sumit; Oswald, Iain D. H.; Pulham, Colin R.; Price, Sarah L.; Reutzel-Edens, Susan M; Journal of the American Chemical Society 141 (2019) 13887–13897; doi:10.1021/jacs.9b06634

data_4128848
_publ_section_title
;
 A Prolific Solvate Former, Galunisertib, under the Pressure of Crystal
 Structure Prediction, Produces Ten Diverse Polymorphs.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13887
_journal_page_last               13897
_journal_paper_doi               10.1021/jacs.9b06634
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C22 H19 N5 O'
_chemical_formula_sum            'C22 H19 N5 O'
_chemical_formula_weight         369.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 133.55(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.938(4)
_cell_length_b                   8.0817(7)
_cell_length_c                   22.004(3)
_cell_measurement_reflns_used    1711
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      54.7540
_cell_measurement_theta_min      5.5360
_cell_volume                     3601(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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    -23.00  73.00   1.00    7.50    --    0.00  38.00 -60.00   96
  2  \w    -86.00 -34.00   1.00    7.50    --    0.00 178.00  90.00   52
  3  \w     -1.00  94.00   1.00   17.50    --   71.40 -38.00   0.00   95
  4  \w      1.00  98.00   1.00   17.50    --   71.40 -57.00  90.00   97
  5  \w     49.00 144.00   1.00   17.50    --   71.40  38.00-150.00   95
  6  \w     94.00 143.00   1.00   17.50    --   71.40 125.00 -60.00   49
  7  \w     94.00 143.00   1.00   17.50    --   71.40 125.00 -90.00   49
  8  \w     -7.00 108.00   1.00   17.50    --   71.40 -19.00-120.00  115
  9  \w    -73.00  23.00   1.00    7.50    --    0.00 -38.00 -60.00   96
 10  \w    -31.00  74.00   1.00    7.50    --    0.00  77.00  30.00  105
 11  \w     45.00 142.00   1.00   17.50    --   71.40  57.00  30.00   97
 12  \w     45.00 106.00   1.00   17.50    --   71.40  57.00 -60.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0079653000
_diffrn_orient_matrix_UB_12      0.1162109000
_diffrn_orient_matrix_UB_13      -0.0558660000
_diffrn_orient_matrix_UB_21      -0.0572485000
_diffrn_orient_matrix_UB_22      -0.1077030000
_diffrn_orient_matrix_UB_23      -0.0309959000
_diffrn_orient_matrix_UB_31      -0.0495510000
_diffrn_orient_matrix_UB_32      0.1060166000
_diffrn_orient_matrix_UB_33      0.0301489000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8913
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        56.285
_diffrn_reflns_theta_max         56.285
_diffrn_reflns_theta_min         4.055
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       plate
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2345
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0681
_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^)+(0.0857P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_ref         0.1761
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1581
_reflns_number_total             2345
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b06634_si_001.cif
_cod_data_source_block           Galunisertib_FORM_X
_cod_original_cell_volume        3600.7(13)
_cod_database_code               4128848
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H19 N5 O'
_chemical_oxdiff_usercomment     'VT sample from pressure cell'
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.921
_reflns_odcompleteness_completeness 99.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.06
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H5A(0.036) H5B(0.036) H14A(0.038) H14B(0.038) H12A(0.04)
 H12B(0.04) H20(0.037) H2(0.033) H13A(0.041) H13B(0.041) H8(0.035) H7(0.036)
 H5(0.029) H18(0.037) H19(0.042) H1(0.034) H22A(0.067) H22B(0.067) H22C(0.067)
 Fixed X: H5A(0.511754) H5B(0.476803) H14A(0.25879) H14B(0.276563)
 H12A(0.440991) H12B(0.38871) H20(0.519972) H2(0.222214) H13A(0.359519)
 H13B(0.317895) H8(0.197979) H7(0.297782) H5(0.393067) H18(0.510559)
 H19(0.56428) H1(0.130846) H22A(0.351104) H22B(0.418532) H22C(0.395833)
 Fixed Y: H5A(0.751332) H5B(0.670548) H14A(0.577475) H14B(0.74762)
 H12A(0.61959) H12B(0.475977) H20(0.229799) H2(0.423993) H13A(0.810897)
 H13B(0.695511) H8(0.648518) H7(0.738994) H5(0.615353) H18(0.060757)
 H19(0.069164) H1(0.450769) H22A(0.170156) H22B(0.1334) H22C(0.320287)
 Fixed Z: H5A(0.317049) H5B(0.34017) H14A(0.419879) H14B(0.400659)
 H12A(0.627413) H12B(0.599044) H20(0.536388) H2(0.291779) H13A(0.53975)
 H13B(0.549017) H8(0.032366) H7(0.077597) H5(0.316441) H18(0.355622)
 H19(0.496851) H1(0.149906) H22A(0.18977) H22B(0.213293) H22C(0.205341)
;
_shelx_res_checksum              66922
_shelx_hkl_checksum              92737
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_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 1.544
_oxdiff_exptl_absorpt_empirical_full_min 0.639