Microbatch under-oil salt screening of organic cations: single-crystal growth of active pharmaceutical ingredients
Babor, Martin; Nievergelt, Philipp P.; Čejka, Jan; Zvoníček, Vít; Spingler, Bernhard; IUCrJ 6 (2019) 145–151; doi:10.1107/S2052252518017876

data_1550453
_publ_section_title
;
 Microbatch under-oil salt screening of organic cations: single-crystal
 growth of active pharmaceutical ingredients
;
_journal_issue                   1
_journal_name_full               IUCrJ
_journal_page_first              145
_journal_page_last               151
_journal_paper_doi               10.1107/S2052252518017876
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C19 H23 Cl N5 O, B F4'
_chemical_formula_sum            'C19 H23 B Cl F4 N5 O'
_chemical_formula_weight         459.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.7648(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.46473(13)
_cell_length_b                   12.98315(16)
_cell_length_c                   13.42014(13)
_cell_measurement_reflns_used    36021
_cell_measurement_temperature    159.99(10)
_cell_measurement_theta_max      78.6160
_cell_measurement_theta_min      3.6800
_cell_volume                     2079.49(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      159.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.962
_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     52.00  83.00   0.50    2.40    --  107.75 -54.00  95.67   62
  2  \w     50.00  86.00   0.50    2.40    --  107.75 -20.00 155.62   72
  3  \w     79.00 106.00   0.50    2.40    --  107.75 -60.00 168.37   54
  4  \w     38.00  66.00   0.50    2.40    --  107.75 -30.00 150.00   56
  5  \w     42.00  77.00   0.50    2.40    --  107.75 -50.00 108.48   70
  6  \w     33.00  85.00   0.50    2.40    --  107.75 -52.00  58.78  104
  7  \w     85.00 111.00   0.50    2.40    --  107.75 -60.00  20.58   52
  8  \w     72.00  98.00   0.50    2.40    --  107.75 -60.00 -42.33   52
  9  \w     58.00  85.00   0.50    2.40    --  107.75 -60.00 -64.42   54
 10  \w     68.00 121.00   0.50    2.40    --  107.75 -60.00-123.70  106
 11  \w    129.00 174.00   0.50    2.40    --  107.75  15.00 -90.00   90
 12  \w    134.00 172.00   0.50    2.40    --  107.75  15.00  30.00   76
 13  \w    146.00 178.00   0.50    2.40    --  107.75  45.00  30.00   64
 14  \w     97.00 122.00   0.50    2.40    --  107.75  15.00  30.00   50
 15  \w    105.00 139.00   0.50    2.40    --  107.75  45.00  30.00   68
 16  \w     64.00 120.00   0.50    2.40    --  107.75 -60.00 -80.02  112
 17  \w     96.00 128.00   0.50    2.40    --  107.75  15.00-150.00   64
 18  \w     53.00 103.00   0.50    2.40    --  107.75 -60.00-162.37  100
 19  \w     47.00  87.00   0.50    2.40    --  107.75 -53.00-114.66   80
 20  \w     44.00  69.00   0.50    2.40    --  107.75 -45.00 -60.00   50
 21  \w     47.00  72.00   0.50    2.40    --  107.75 -48.00 -19.73   50
 22  \w     54.00  79.00   0.50    2.40    --  107.75 -49.00  11.90   50
 23  \w     37.00  63.00   0.50    2.40    --  107.75 -52.00 -23.37   52
 24  \w     37.00  71.00   0.50    2.40    --  107.75 -53.00 -28.90   68
 25  \w     40.00  65.00   0.50    2.40    --  107.75 -60.00  20.58   50
 26  \w     37.00  63.00   0.50    2.40    --  107.75 -30.00  60.00   52
 27  \w     44.00  78.00   0.50    2.40    --  107.75 -46.00  55.58   68
 28  \w     34.00  68.00   0.50    2.40    --  107.75 -30.00  90.00   68
 29  \w     43.00  92.00   0.50    2.40    --  107.75  -4.00  59.26   98
 30  \w     35.00  61.00   0.50    0.60    --   50.46  57.00 -30.00   52
 31  \w     36.00  64.00   0.50    0.60    --   50.46  57.00   0.00   56
 32  \w     37.00  63.00   0.50    2.40    --  107.75 -60.00 168.37   52
 33  \w    -79.00 -43.00   0.50    0.60    --  -50.46 -19.00 -60.00   72
 34  \w    -23.00  19.00   0.50    0.60    --  -50.46  57.00  60.00   84
 35  \w    -58.00 -27.00   0.50    0.60    --  -50.46  57.00  60.00   62
 36  \w    -65.00 -39.00   0.50    2.40    --  -86.25  60.00  21.93   52
 37  \w   -116.00 -35.00   0.50    0.60    --  -50.46 -57.00-120.00  162
 38  \w   -125.00 -81.00   0.50    0.60    --  -50.46 -19.00 -60.00   88
 39  \w    -62.00 -24.00   0.50    0.60    --  -50.46  38.00 -60.00   76
 40  \w    -45.00  -9.00   0.50    0.60    --  -50.46  38.00-180.00   72
 41  \w     -5.00  21.00   0.50    0.60    --  -50.46  38.00-180.00   52
 42  \w     37.00  64.00   0.50    0.60    --   50.46  60.00  47.85   54
 43  \w     36.00  71.00   0.50    0.60    --   50.46  57.00   0.00   70
 44  \w     38.00  64.00   0.50    0.60    --   50.46  57.00  30.00   52
 45  \w     36.00  63.00   0.50    0.60    --   50.46  57.00-120.00   54
 46  \w     40.00  83.00   0.50    0.60    --   50.46  19.00 -30.00   86
 47  \w     23.00  62.00   0.50    0.60    --   50.46 -57.00-120.00   78
 48  \w     44.00  73.00   0.50    0.60    --   50.46  38.00 -90.00   58
 49  \w     37.00  64.00   0.50    0.60    --   50.46  60.00 -83.29   54
 50  \w    -96.00 -71.00   0.50    2.40    --  -86.25 -59.00 -65.41   50
 51  \w   -101.00 -75.00   0.50    2.40    --  -86.25 -58.00   4.64   52
 52  \w    -98.00 -72.00   0.50    2.40    --  -86.25 -60.00  17.66   52
 53  \w    -98.00 -71.00   0.50    2.40    --  -86.25 -59.00 -13.45   54
 54  \w    -96.00 -70.00   0.50    2.40    --  -86.25 -60.00-105.68   52
 55  \w   -101.00 -75.00   0.50    2.40    --  -86.25 -57.00-118.61   52
 56  \w    -97.00 -71.00   0.50    2.40    --  -86.25 -59.00-122.77   52
 57  \w    -97.00 -71.00   0.50    2.40    --  -86.25 -60.00 -97.25   52
 58  \w    -97.00 -71.00   0.50    2.40    --  -86.25 -60.00 -75.32   52
 59  \w    -96.00 -71.00   0.50    2.40    --  -86.25 -59.00 -32.53   50
 60  \w    -98.00 -72.00   0.50    2.40    --  -86.25 -56.00 -53.38   52
 61  \w    -95.00 -70.00   0.50    2.40    --  -86.25 -60.00 -82.23   50
 62  \w   -107.00 -70.00   0.50    2.40    --  -86.25 -60.00-137.53   74
 63  \w    -97.00 -71.00   0.50    2.40    --  -86.25 -58.00   7.93   52
 64  \w    -96.00 -71.00   0.50    2.40    --  -86.25 -57.00 -94.82   50
 65  \w    -98.00 -72.00   0.50    2.40    --  -86.25 -53.00 -74.48   52
 66  \w    -96.00 -70.00   0.50    2.40    --  -86.25 -60.00 -27.53   52
 67  \w    -97.00 -71.00   0.50    2.40    --  -86.25 -59.00 -20.69   52
 68  \w    -98.00 -71.00   0.50    2.40    --  -86.25 -58.00-114.40   54
 69  \w    -99.00 -72.00   0.50    2.40    --  -86.25 -59.00 -56.20   54
 70  \w    -96.00 -70.00   0.50    2.40    --  -86.25 -60.00  -9.62   52
 71  \w    -98.00 -72.00   0.50    2.40    --  -86.25 -56.00  -6.79   52
 72  \w    -97.00 -71.00   0.50    2.40    --  -86.25 -60.00 -38.53   52
 73  \w     95.00 120.00   0.50    2.40    --  107.75  45.00  30.00   50
 74  \w     94.00 120.00   0.50    2.40    --  107.75  45.00   0.00   52
 75  \w    120.00 146.00   0.50    2.40    --  107.75   4.00-123.74   52
 76  \w     63.00 101.00   0.50    2.40    --  107.75   4.00-123.74   76
 77  \w     95.00 121.00   0.50    2.40    --  107.75  47.00  70.26   52
 78  \w    110.00 157.00   0.50    2.40    --  107.75  30.00  90.00   94
 79  \w     96.00 131.00   0.50    2.40    --  107.75  45.00  60.00   70
 80  \w    145.00 177.00   0.50    2.40    --  107.75  60.00 144.46   64
 81  \w     50.00  76.00   0.50    2.40    --  107.75 -45.00-150.00   52
 82  \w    111.00 137.00   0.50    2.40    --  107.75  30.00 -60.00   52
 83  \w    102.00 153.00   0.50    2.40    --  107.75  45.00  90.00  102
 84  \w    105.00 131.00   0.50    2.40    --  107.75  30.00  30.00   52
 85  \w    101.00 126.00   0.50    2.40    --  107.75  60.00 144.46   50
 86  \w    104.00 131.00   0.50    2.40    --  107.75  30.00 -30.00   54
 87  \w    153.00 178.00   0.50    2.40    --  107.75  45.00 120.00   50
 88  \w     97.00 128.00   0.50    2.40    --  107.75  45.00 -90.00   62
 89  \w     95.00 121.00   0.50    2.40    --  107.75  15.00  60.00   52
 90  \w    115.00 141.00   0.50    2.40    --  107.75  30.00   0.00   52
 91  \w    146.00 172.00   0.50    2.40    --  107.75  49.00-132.85   52
 92  \w    100.00 125.00   0.50    2.40    --  107.75  45.00 120.00   50
 93  \w     94.00 138.00   0.50    2.40    --  107.75  45.00 -30.00   88
 94  \w     98.00 124.00   0.50    2.40    --  107.75  49.00-132.85   52
 95  \w    138.00 164.00   0.50    2.40    --  107.75  45.00-180.00   52
 96  \w     98.00 136.00   0.50    2.40    --  107.75  45.00-180.00   76
 97  \w     32.00  69.00   0.50    2.40    --  107.75 -30.00   0.00   74
 98  \w     94.00 147.00   0.50    2.40    --  107.75  45.00 -60.00  106
 99  \w     99.00 127.00   0.50    2.40    --  107.75  40.00   0.78   56
100  \w     86.00 112.00   0.50    2.40    --  107.75 -60.00 -54.81   52
101  \w     40.00  66.00   0.50    2.40    --  107.75 -60.00 -54.81   52
102  \w     92.00 117.00   0.50    2.40    --  107.75 -15.00  90.00   50
103  \w    143.00 173.00   0.50    2.40    --  107.75  47.00  70.26   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0103051000
_diffrn_orient_matrix_UB_12      -0.0148874000
_diffrn_orient_matrix_UB_13      0.1107700000
_diffrn_orient_matrix_UB_21      -0.1279942000
_diffrn_orient_matrix_UB_22      0.0141188000
_diffrn_orient_matrix_UB_23      -0.0417587000
_diffrn_orient_matrix_UB_31      -0.0141502000
_diffrn_orient_matrix_UB_32      -0.1167544000
_diffrn_orient_matrix_UB_33      -0.0191807000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            48534
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.777
_diffrn_reflns_theta_min         3.704
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.148
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.531
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
   a multifaceted crystal model
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    1.468
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.017
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0247P)^2^+2.2045P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4165
_reflns_number_total             4315
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lt5016.cif
_cod_data_source_block           pn180817_uo_trh_1_180814_b1_bf4
_cod_database_code               1550453
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C19 H23 B Cl F4 N5 O'
_reflns_odcompleteness_completeness 95.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     79.66
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Others
 Sof(F1)=Sof(F2)=Sof(F3)=1-FVAR(1)
 Sof(F29)=Sof(F27)=Sof(F30)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 N16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C18(H18A,H18B), C17(H17A,H17B), C15(H15A,
 H15B), C10(H10A,H10B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C4(H4), C24(H24), C23(H23), C22(H22), C7(H7), C5(H5), C6(H6)
;
_shelx_res_checksum              85548
_shelx_hkl_checksum              74908
_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 1.227
_oxdiff_exptl_absorpt_empirical_full_min 0.783