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_1550450
_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         'C10 H16 N O, C5 H6 N O3, H2 O'
_chemical_formula_sum            'C15 H24 N2 O5'
_chemical_formula_weight         312.36
_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   mixed
_audit_creation_date             2018-08-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.9780(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.47377(11)
_cell_length_b                   6.14747(5)
_cell_length_c                   11.71348(12)
_cell_measurement_reflns_used    12100
_cell_measurement_temperature    159.99(10)
_cell_measurement_theta_max      78.6290
_cell_measurement_theta_min      4.0570
_cell_volume                     766.164(14)
_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)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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    143.00 178.00   0.50    2.00    --  107.75  45.00 120.00   70
  2  \w    148.00 177.00   0.50    2.00    --  107.75  57.00  69.33   58
  3  \w    146.00 175.00   0.50    2.00    --  107.75  15.00  30.00   58
  4  \w    143.00 178.00   0.50    2.00    --  107.75  45.00 -30.00   70
  5  \w    144.00 171.00   0.50    2.00    --  107.75  15.00 -90.00   54
  6  \w    142.00 168.00   0.50    2.00    --  107.75  15.00-120.00   52
  7  \w    134.00 170.00   0.50    2.00    --  107.75  45.00-120.00   72
  8  \w    129.00 163.00   0.50    2.00    --  107.75  45.00   0.00   68
  9  \w    128.00 154.00   0.50    2.00    --  107.75  45.00  60.00   52
 10  \w    128.00 167.00   0.50    2.00    --  107.75  40.00  55.22   78
 11  \w    111.00 137.00   0.50    2.00    --  107.75  15.00  30.00   52
 12  \w    108.00 134.00   0.50    2.00    --  107.75  45.00 -30.00   52
 13  \w    100.00 139.00   0.50    2.00    --  107.75  45.00  30.00   78
 14  \w    103.00 131.00   0.50    2.00    --  107.75  45.00  90.00   56
 15  \w    103.00 129.00   0.50    2.00    --  107.75  45.00 120.00   52
 16  \w    103.00 140.00   0.50    2.00    --  107.75  30.00 150.00   74
 17  \w     96.00 132.00   0.50    2.00    --  107.75  30.00 120.00   72
 18  \w     94.00 129.00   0.50    2.00    --  107.75  57.00  69.33   70
 19  \w     94.00 139.00   0.50    2.00    --  107.75  45.00 150.00   90
 20  \w     95.00 121.00   0.50    2.00    --  107.75  45.00  60.00   52
 21  \w     96.00 121.00   0.50    2.00    --  107.75  40.00  55.22   50
 22  \w     62.00  88.00   0.50    2.00    --  107.75 -15.00 150.00   52
 23  \w     36.00 124.00   0.50    0.50    --   50.71  57.00 120.00  176
 24  \w     49.00  75.00   0.50    2.00    --  107.75 -15.00 -30.00   52
 25  \w     74.00 100.00   0.50    2.00    --  107.75 -59.00 -19.47   52
 26  \w     80.00 106.00   0.50    2.00    --  107.75  -8.00-100.61   52
 27  \w     85.00 115.00   0.50    2.00    --  107.75 -15.00-180.00   60
 28  \w     59.00  85.00   0.50    2.00    --  107.75 -54.00-171.92   52
 29  \w     56.00  88.00   0.50    2.00    --  107.75 -54.00-144.42   64
 30  \w     55.00  80.00   0.50    2.00    --  107.75 -54.00 -97.01   50
 31  \w     49.00  85.00   0.50    2.00    --  107.75 -57.00-105.58   72
 32  \w     38.00  76.00   0.50    2.00    --  107.75 -45.00 -60.00   76
 33  \w     43.00  71.00   0.50    2.00    --  107.75 -49.00  18.32   56
 34  \w     36.00  88.00   0.50    2.00    --  107.75 -53.00  44.59  104
 35  \w     37.00  65.00   0.50    2.00    --  107.75 -30.00 -60.00   56
 36  \w     34.00  80.00   0.50    2.00    --  107.75 -50.00  -0.20   92
 37  \w     30.00  64.00   0.50    2.00    --  107.75 -30.00  60.00   68
 38  \w     35.00  90.00   0.50    2.00    --  107.75 -57.00  95.29  110
 39  \w     34.00  78.00   0.50    2.00    --  107.75 -53.00 178.23   88
 40  \w     39.00  88.00   0.50    2.00    --  107.75 -60.00 161.56   98
 41  \w     39.00  68.00   0.50    2.00    --  107.75 -30.00 120.00   58
 42  \w     35.00  61.00   0.50    2.00    --  107.75 -53.00  60.74   52
 43  \w     32.00  67.00   0.50    2.00    --  107.75 -30.00   0.00   70
 44  \w     39.00  65.00   0.50    2.00    --  107.75 -30.00-150.00   52
 45  \w     31.00  65.00   0.50    2.00    --  107.75 -30.00-180.00   68
 46  \w    -22.00  66.00   0.50    0.50    --   50.71 -57.00 -30.00  176
 47  \w    -69.00  -8.00   0.50    2.00    --  -86.25  30.00 120.00  122
 48  \w    -97.00 -70.00   0.50    2.00    --  -86.25 -60.00  73.44   54
 49  \w    -95.00 -70.00   0.50    2.00    --  -86.25 -60.00  61.00   50
 50  \w   -124.00 -36.00   0.50    0.50    --  -50.71 -56.00  80.71  176
 51  \w   -128.00 -39.00   0.50    0.50    --  -50.71 -38.00-120.00  178
 52  \w   -128.00 -39.00   0.50    0.50    --  -50.71 -38.00 120.00  178
 53  \w   -128.00 -39.00   0.50    0.50    --  -50.71 -41.00 176.00  178
 54  \w   -158.00 -70.00   0.50    2.00    --  -86.25 -60.00  25.37  176
 55  \w   -149.00 -72.00   0.50    2.00    --  -86.25 -60.00  35.81  154
 56  \w   -161.00 -73.00   0.50    2.00    --  -86.25 -49.00  88.37  176
 57  \w   -160.00 -72.00   0.50    2.00    --  -86.25 -54.00  38.74  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      0.1195062000
_diffrn_orient_matrix_UB_12      -0.0385301000
_diffrn_orient_matrix_UB_13      -0.0275917000
_diffrn_orient_matrix_UB_21      0.0595102000
_diffrn_orient_matrix_UB_22      -0.1240044000
_diffrn_orient_matrix_UB_23      0.1224599000
_diffrn_orient_matrix_UB_31      -0.0559583000
_diffrn_orient_matrix_UB_32      -0.2144269000
_diffrn_orient_matrix_UB_33      -0.0659819000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13893
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.863
_diffrn_reflns_theta_min         4.070
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.708
_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    1.354
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1425 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3268
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0246
_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^)+(0.0385P)^2^+0.1159P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0656
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                3223
_reflns_number_total             3268
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lt5016.cif
_cod_data_source_block           pn180815_uo_eph_1_180814_pyrolidcarbox
_cod_original_cell_volume        766.163(14)
_cod_database_code               1550450
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C15 H25 N2 O5'
_reflns_odcompleteness_completeness 99.07
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Ternary CH refined with riding coordinates:
 C1(H1C), C2(H2), C12(H12)
2.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C13(H13A,H13B), C14(H14A,H14B)
2.d Aromatic/amide H refined with riding coordinates:
 N2(H2A), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
2.e Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              67692
_shelx_hkl_checksum              49217
_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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.788