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_1550457
_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 rm
_chemical_formula_moiety         'C10 H16 N O, N O3'
_chemical_formula_sum            'C10 H16 N2 O4'
_chemical_formula_weight         228.25
_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
_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                 112.806(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0401(3)
_cell_length_b                   29.3553(8)
_cell_length_c                   7.3828(3)
_cell_measurement_reflns_used    5146
_cell_measurement_temperature    159.99(10)
_cell_measurement_theta_max      76.7640
_cell_measurement_theta_min      6.0240
_cell_volume                     1206.70(10)
_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_temperature      160.15
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.934
_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    140.00 169.00   0.50   32.00    --  104.56  30.00 -60.00   58
  2  \w    147.00 176.00   0.50   32.00    --  104.56  15.00  60.00   58
  3  \w     96.00 129.00   0.50   32.00    --  104.56  15.00  60.00   66
  4  \w     92.00 154.00   0.50   32.00    --  104.56  15.00  90.00  124
  5  \w     98.00 137.00   0.50   32.00    --  104.56  30.00 -60.00   78
  6  \w     92.00 178.00   0.50   32.00    --  104.56  15.00-150.00  172
  7  \w     83.00 112.00   0.50   32.00    --  104.56 -60.00-106.07   58
  8  \w     82.00 109.00   0.50   32.00    --  104.56 -60.00-125.32   54
  9  \w     71.00 111.00   0.50   32.00    --  104.56 -60.00 -29.27   80
 10  \w     65.00  90.00   0.50   32.00    --  104.56 -59.00  25.05   50
 11  \w     63.00  90.00   0.50   32.00    --  104.56 -60.00  64.66   54
 12  \w     74.00 100.00   0.50   32.00    --  104.56 -59.00 120.71   52
 13  \w     76.00 104.00   0.50   32.00    --  104.56 -60.00 157.05   56
 14  \w     51.00  96.00   0.50   32.00    --  104.56 -60.00 177.08   90
 15  \w     46.00  71.00   0.50   32.00    --  104.56 -59.00  74.38   50
 16  \w     46.00  83.00   0.50   32.00    --  104.56 -60.00  49.91   74
 17  \w     33.00  68.00   0.50   32.00    --  104.56 -60.00 -29.27   70
 18  \w     26.00  69.00   0.50   32.00    --  104.56 -30.00  30.00   86
 19  \w     33.00  92.00   0.50   32.00    --  104.56 -59.00 102.56  118
 20  \w     33.00  83.00   0.50   32.00    --  104.56 -59.00   2.26  100
 21  \w     28.00  63.00   0.50   32.00    --  104.56 -30.00 120.00   70
 22  \w      7.00  34.00   0.50    8.00    --    2.14  57.00  60.00   54
 23  \w     36.00  67.00   0.50    8.00    --    2.14  57.00  60.00   62
 24  \w     34.00 117.00   0.50   32.00    --  104.56 -60.00-153.60  166
 25  \w    -66.00  17.00   0.50    8.00    --    2.14 -57.00  60.00  166
 26  \w    -66.00  -9.00   0.50   32.00    --  -86.25  30.00 -90.00  114
 27  \w    -73.00 -43.00   0.50   32.00    --  -86.25  60.00   7.06   60
 28  \w    -68.00 -31.00   0.50   32.00    --  -86.25  30.00   0.00   74
 29  \w    -73.00 -16.00   0.50   32.00    --  -86.25  60.00 -76.86  114
 30  \w    -73.00 -47.00   0.50   32.00    --  -86.25  59.00-133.04   52
 31  \w    -75.00  13.00   0.50    8.00    --    2.14 -19.00-180.00  176
 32  \w    -96.00 -21.00   0.50   32.00    --  -86.25  60.00  67.78  150
 33  \w   -101.00 -57.00   0.50   32.00    --  -86.25  60.00 175.53   88
 34  \w   -118.00 -85.00   0.50   32.00    --  -86.25 -58.00-123.65   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12312
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.052
_diffrn_reflns_theta_min         6.030
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.811
_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    1.256
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.396
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.139
_refine_ls_abs_structure_details
;
 Flack x determined using 1465 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4637
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0676
_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^)+(0.1253P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1823
_refine_ls_wR_factor_ref         0.1902
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.877
_reflns_number_gt                3727
_reflns_number_total             4637
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lt5016.cif
_cod_data_source_block           pn180914_uo_eph_2_180814_c6_scr2
_cod_original_cell_volume        1206.70(9)
_cod_database_code               1550457
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.737
_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. Uiso/Uaniso restraints and constraints
O15 \\sim O16 \\sim O17: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
3.a Ternary CH refined with riding coordinates:
 C1(H1C), C2(H2), C11(H11C), C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N11(H11A,H11B)
3.c 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.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O11(H11)
;
_shelx_res_checksum              26731
_shelx_hkl_checksum              65547
_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
;