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_1550454
_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_absolute_configuration rmad
_chemical_formula_moiety         'C6 H5 O3 S, C10 H16 N O'
_chemical_formula_sum            'C16 H21 N O4 S'
_chemical_formula_weight         323.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.3547(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.72587(4)
_cell_length_b                   20.83882(10)
_cell_length_c                   6.92054(4)
_cell_measurement_reflns_used    12545
_cell_measurement_temperature    159.99(10)
_cell_measurement_theta_max      78.6210
_cell_measurement_theta_min      6.3580
_cell_volume                     816.998(8)
_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 0.960
_diffrn_measured_fraction_theta_max 0.937
_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     35.00 123.00   0.50    1.00    --   50.46  57.00  60.00  176
  2  \w     94.00 173.00   0.50    1.00    --  107.75  30.00 150.00  158
  3  \w    137.00 176.00   0.50    1.00    --  107.75  30.00  60.00   78
  4  \w    144.00 178.00   0.50    1.00    --  107.75  15.00  30.00   68
  5  \w    143.00 169.00   0.50    1.00    --  107.75  45.00 -30.00   52
  6  \w    126.00 156.00   0.50    1.00    --  107.75  30.00 -60.00   60
  7  \w    104.00 130.00   0.50    1.00    --  107.75  45.00-150.00   52
  8  \w    146.00 177.00   0.50    1.00    --  107.75  45.00-150.00   62
  9  \w     87.00 113.00   0.50    1.00    --  107.75 -15.00 -30.00   52
 10  \w     81.00 108.00   0.50    1.00    --  107.75 -60.00  -6.14   54
 11  \w     98.00 124.00   0.50    1.00    --  107.75 -60.00  47.66   52
 12  \w     83.00 114.00   0.50    1.00    --  107.75 -60.00  17.62   62
 13  \w     74.00 101.00   0.50    1.00    --  107.75 -60.00  12.20   54
 14  \w     66.00 103.00   0.50    1.00    --  107.75 -60.00 -38.95   74
 15  \w     60.00  97.00   0.50    1.00    --  107.75 -58.00 -67.09   74
 16  \w     70.00 103.00   0.50    1.00    --  107.75 -60.00-125.43   66
 17  \w     53.00  97.00   0.50    1.00    --  107.75 -59.00-163.36   88
 18  \w     42.00  68.00   0.50    1.00    --  107.75 -45.00 -60.00   52
 19  \w     37.00  63.00   0.50    1.00    --  107.75 -46.00-103.25   52
 20  \w     35.00  61.00   0.50    1.00    --  107.75 -45.00 -90.00   52
 21  \w     31.00  57.00   0.50    1.00    --  107.75 -30.00 -30.00   52
 22  \w     49.00  75.00   0.50    1.00    --  107.75 -59.00  28.74   52
 23  \w     46.00  79.00   0.50    1.00    --  107.75 -60.00  47.66   66
 24  \w     40.00 101.00   0.50    1.00    --  107.75 -59.00  90.67  122
 25  \w     74.00 100.00   0.50    1.00    --  107.75 -59.00 151.13   52
 26  \w     50.00  76.00   0.50    1.00    --  107.75 -47.00 163.55   52
 27  \w     34.00  61.00   0.50    1.00    --  107.75 -30.00 150.00   54
 28  \w     37.00  82.00   0.50    1.00    --  107.75 -54.00 138.66   90
 29  \w     41.00  67.00   0.50    1.00    --  107.75 -55.00 152.04   52
 30  \w     37.00  90.00   0.50    1.00    --  107.75 -57.00 117.87  106
 31  \w     41.00  66.00   0.50    1.00    --  107.75 -30.00  90.00   50
 32  \w     31.00  65.00   0.50    1.00    --  107.75 -30.00  60.00   68
 33  \w     38.00  64.00   0.50    1.00    --  107.75 -60.00  -6.14   52
 34  \w     32.00  58.00   0.50    1.00    --  107.75 -45.00  60.00   52
 35  \w     95.00 120.00   0.50    1.00    --  107.75  30.00  60.00   50
 36  \w    126.00 152.00   0.50    1.00    --  107.75  30.00  90.00   52
 37  \w     98.00 170.00   0.50    1.00    --  107.75  45.00  90.00  144
 38  \w     36.00 103.00   0.50    1.00    --   50.46  59.00  74.74  134
 39  \w     35.00 123.00   0.50    1.00    --   50.46  57.00  40.29  176
 40  \w     35.00 123.00   0.50    1.00    --   50.46  57.00 -90.00  176
 41  \w     35.00 123.00   0.50    1.00    --   50.46  57.00   0.00  176
 42  \w     35.00  61.00   0.50    1.00    --  107.75 -56.00-106.50   52
 43  \w     39.00  76.00   0.50    1.00    --  107.75 -45.00-150.00   74
 44  \w     36.00  89.00   0.50    1.00    --  107.75 -59.00 -95.48  106
 45  \w    -22.00  66.00   0.50    1.00    --   50.46 -57.00 -60.00  176
 46  \w    -22.00  66.00   0.50    1.00    --   50.46 -57.00-120.00  176
 47  \w    -74.00 -49.00   0.50    1.00    --  -86.25  60.00 -38.01   50
 48  \w   -128.00 -38.00   0.50    1.00    --  -50.46 -38.00 -30.00  180
 49  \w     29.00  55.00   0.50    1.00    --  107.75 -15.00 150.00   52
 50  \w   -123.00 -35.00   0.50    1.00    --  -50.46 -57.00 120.00  176
 51  \w   -123.00 -35.00   0.50    1.00    --  -50.46 -57.00 -60.00  176
 52  \w   -123.00 -35.00   0.50    1.00    --  -50.46 -57.00-150.00  176
 53  \w   -123.00 -35.00   0.50    1.00    --  -50.46 -57.00-120.00  176
;
_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      0.0761803000
_diffrn_orient_matrix_UB_12      -0.0457499000
_diffrn_orient_matrix_UB_13      0.1726057000
_diffrn_orient_matrix_UB_21      0.0735571000
_diffrn_orient_matrix_UB_22      0.0579945000
_diffrn_orient_matrix_UB_23      0.1330496000
_diffrn_orient_matrix_UB_31      -0.2504642000
_diffrn_orient_matrix_UB_32      0.0031092000
_diffrn_orient_matrix_UB_33      0.0559553000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_unetI/netI     0.0081
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13481
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.844
_diffrn_reflns_theta_min         6.465
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.912
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.488
_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    1.315
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.702
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1579 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(5)
_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     202
_refine_ls_number_reflns         3292
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0230
_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^)+(0.0414P)^2^+0.1072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0611
_reflns_Friedel_coverage         0.936
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                3290
_reflns_number_total             3292
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lt5016.cif
_cod_data_source_block           pn180830_uo_eph_1_180814_b12_benzsulf
_cod_database_code               1550454
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C16 H21 N O4 S'
_shelx_estimated_absorpt_t_max   0.737
_shelx_estimated_absorpt_t_min   0.347
_reflns_odcompleteness_completeness 92.74
_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 N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1C), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C10(H10), C9(H9), C12(H12), C6(H6), C8(H8), C15(H15), C13(H13),
 C7(H7), C14(H14)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C3(H3A,H3B,H3C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              5623
_shelx_hkl_checksum              98366
_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 1.214
_oxdiff_exptl_absorpt_empirical_full_min 0.805