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_1550456
_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         '2(C10 H16 N O), C4 H4 O6, H2 O'
_chemical_formula_sum            'C24 H38 N2 O9'
_chemical_formula_weight         498.56
_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             2018-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.168(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.07189(12)
_cell_length_b                   32.9414(4)
_cell_length_c                   7.13830(10)
_cell_measurement_reflns_used    17545
_cell_measurement_temperature    159.99(10)
_cell_measurement_theta_max      78.6170
_cell_measurement_theta_min      5.3390
_cell_volume                     1302.63(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)'
_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 0.969
_diffrn_measured_fraction_theta_max 0.948
_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    -66.00  22.00   0.50    1.25    --  -50.46  57.00-180.00  176
  2  \w    -69.00  -8.00   0.50    5.00    --  -86.25  30.00 -60.00  122
  3  \w   -102.00 -15.00   0.50    5.00    --  -86.25  60.00 -97.86  174
  4  \w   -102.00 -15.00   0.50    5.00    --  -86.25  60.00 -15.03  174
  5  \w   -123.00 -35.00   0.50    1.25    --  -50.46 -57.00-120.00  176
  6  \w   -123.00 -35.00   0.50    1.25    --  -50.46 -57.00  30.00  176
  7  \w   -123.00 -35.00   0.50    1.25    --  -50.46 -57.00 -30.00  176
  8  \w   -123.00 -35.00   0.50    1.25    --  -50.46 -57.00-150.00  176
  9  \w     35.00 123.00   0.50    1.25    --   50.46  57.00 -90.00  176
 10  \w     94.00 178.00   0.50    5.00    --  107.75  30.00   0.00  168
 11  \w     96.00 121.00   0.50    5.00    --  107.75  15.00  30.00   50
 12  \w     95.00 165.00   0.50    5.00    --  107.75  15.00  60.00  140
 13  \w     98.00 175.00   0.50    5.00    --  107.75  15.00 -30.00  154
 14  \w     93.00 178.00   0.50    5.00    --  107.75  57.00-110.49  170
 15  \w     72.00  98.00   0.50    5.00    --  107.75 -59.00 -80.05   52
 16  \w     65.00  91.00   0.50    5.00    --  107.75 -15.00-150.00   52
 17  \w     64.00  93.00   0.50    5.00    --  107.75 -57.00-155.80   58
 18  \w     54.00  95.00   0.50    5.00    --  107.75 -59.00-102.83   82
 19  \w     53.00  78.00   0.50    5.00    --  107.75 -46.00 -32.90   50
 20  \w     70.00  95.00   0.50    5.00    --  107.75 -59.00  23.23   50
 21  \w     71.00  99.00   0.50    5.00    --  107.75 -58.00  47.30   56
 22  \w     84.00 118.00   0.50    5.00    --  107.75 -15.00  90.00   68
 23  \w     36.00 124.00   0.50    5.00    --  107.75 -60.00 -51.42  176
 24  \w     47.00  72.00   0.50    5.00    --  107.75 -46.00-134.53   50
 25  \w     34.00  87.00   0.50    5.00    --  107.75 -53.00-174.09  106
 26  \w     36.00 124.00   0.50    5.00    --  107.75 -60.00-142.49  176
 27  \w     35.00 123.00   0.50    1.25    --   50.46  57.00-120.00  176
 28  \w     28.00 123.00   0.50    5.00    --  107.75  -9.00  39.84  190
 29  \w     42.00  68.00   0.50    5.00    --  107.75 -58.00  47.30   52
 30  \w     35.00  96.00   0.50    5.00    --  107.75 -57.00  92.06  122
 31  \w     42.00  83.00   0.50    5.00    --  107.75 -60.00 178.46   82
 32  \w     29.00  69.00   0.50    5.00    --  107.75 -30.00 150.00   80
 33  \w     33.00  82.00   0.50    5.00    --  107.75 -49.00  60.59   98
 34  \w     35.00  99.00   0.50    5.00    --  107.75 -58.00 138.61  128
 35  \w     36.00 124.00   0.50    5.00    --  107.75 -60.00  77.95  176
 36  \w     34.00  91.00   0.50    5.00    --  107.75 -55.00  26.55  114
 37  \w     36.00 124.00   0.50    5.00    --  107.75 -60.00 110.35  176
 38  \w     35.00  98.00   0.50    5.00    --  107.75 -15.00  30.00  126
 39  \w     28.00 124.00   0.50    5.00    --  107.75  -8.00 159.64  192
 40  \w     37.00  81.00   0.50    5.00    --  107.75 -60.00 160.60   88
 41  \w     29.00  54.00   0.50    5.00    --  107.75 -30.00 120.00   50
 42  \w     30.00  68.00   0.50    5.00    --  107.75 -30.00  30.00   76
 43  \w     32.00  69.00   0.50    5.00    --  107.75 -30.00   0.00   74
 44  \w     34.00  71.00   0.50    5.00    --  107.75 -45.00 -60.00   74
 45  \w     29.00  69.00   0.50    5.00    --  107.75 -30.00-120.00   80
 46  \w     38.00  63.00   0.50    5.00    --  107.75 -57.00-155.80   50
 47  \w     35.00  74.00   0.50    5.00    --  107.75 -45.00-150.00   78
 48  \w     35.00  68.00   0.50    5.00    --  107.75 -30.00-150.00   66
 49  \w   -158.00 -71.00   0.50    5.00    --  -86.25 -59.00-150.89  174
 50  \w   -158.00 -71.00   0.50    5.00    --  -86.25 -59.00-132.12  174
 51  \w   -159.00 -71.00   0.50    5.00    --  -86.25 -58.00-118.94  176
 52  \w   -158.00 -70.00   0.50    5.00    --  -86.25 -60.00-110.71  176
 53  \w   -158.00 -71.00   0.50    5.00    --  -86.25 -59.00-139.45  174
 54  \w   -159.00 -71.00   0.50    5.00    --  -86.25 -58.00-171.53  176
 55  \w   -158.00 -70.00   0.50    5.00    --  -86.25 -60.00-147.70  176
 56  \w   -158.00 -70.00   0.50    5.00    --  -86.25 -60.00 171.31  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      0.0939548000
_diffrn_orient_matrix_UB_12      0.0287795000
_diffrn_orient_matrix_UB_13      0.1864811000
_diffrn_orient_matrix_UB_21      -0.0274115000
_diffrn_orient_matrix_UB_22      0.0362923000
_diffrn_orient_matrix_UB_23      -0.1440192000
_diffrn_orient_matrix_UB_31      -0.2602706000
_diffrn_orient_matrix_UB_32      0.0065544000
_diffrn_orient_matrix_UB_33      -0.0210994000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            31569
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.748
_diffrn_reflns_theta_min         5.371
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.370
_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    1.271
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.476
_exptl_crystal_size_mid          0.346
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2347 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5216
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0481P)^2^+0.7643P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_full    0.950
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                5091
_reflns_number_total             5216
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lt5016.cif
_cod_data_source_block           pn180914_uo_eph_1_180814_g5_tart
_cod_database_code               1550456
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C24 H20 O9 N2'
_reflns_odcompleteness_completeness 93.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     79.66
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups, H23A of C23, H22 of C22, H20 of C20, H17 of C17, H16 of
  C16, H19 of C19, H18 of C18, H11C of C11, H8 of C8, H1C of C1, H2 of C2, H9
  of C9, H6 of C6, H12 of C12, H7 of C7, H10 of C10
 At 1.5 times of:
  All C(H,H,H) groups, H23 of C17, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O23-H23
 0.86 with sigma of 0.02
3.a Free rotating group:
 O27(H27A,H27B)
3.b Ternary CH refined with riding coordinates:
 C1(H1C), C2(H2), C11(H11C), C12(H12), C22(H22), C23(H23A)
3.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N11(H11A,H11B)
3.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
3.e Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
3.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O11(H11), O24(H24)
;
_shelx_res_checksum              53696
_shelx_hkl_checksum              18398
_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 1.743
_oxdiff_exptl_absorpt_empirical_full_min 0.713