Overcoming a solid solution system on chiral resolution: combining crystallization and enantioselective dissolution.
Oketani, Ryusei; Shiohara, Koki; Hisaki, Ichiro; Chemical communications (Cambridge, England) 59 (2023) 6175–6178; doi:10.1039/d3cc01352a

data_7131562
_publ_section_title
;
 Overcoming a solid solution system on chiral resolution: combining
 crystallization and enantioselective dissolution.
;
_journal_issue                   41
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6175
_journal_page_last               6178
_journal_paper_doi               10.1039/d3cc01352a
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H17 O8, C10 H11 N2'
_chemical_formula_sum            'C30 H28 N2 O8'
_chemical_formula_weight         544.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-04-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-08 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.9768(2)
_cell_length_b                   29.4996(6)
_cell_length_c                   23.6631(5)
_cell_measurement_reflns_used    30810
_cell_measurement_temperature    113
_cell_measurement_theta_max      30.0070
_cell_measurement_theta_min      2.2190
_cell_volume                     5568.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      113
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.951
_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    -97.00  67.00   0.25    5.00    --   -7.00  45.00 193.00  656
  2  \w    -97.00  59.25   0.25    5.00    --   -7.00  45.00 122.00  625
  3  \w    -61.00  56.00   0.25    5.00    --   -7.00  45.00  51.00  468
  4  \w     35.75  83.00   0.25    5.00    --   -7.00  45.00 264.00  189
  5  \w    -84.00  56.00   0.25    5.00    --   -7.00  45.00  15.00  560
  6  \w     12.00  57.00   0.25    5.00    --   -7.00  45.00 228.00  180
  7  \w    -97.00 -52.00   0.25    5.00    --   -7.00  45.00 -20.00  180
  8  \w    -97.00 -48.00   0.25    5.00    --   -7.00  45.00  86.00  196
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0107856000
_diffrn_orient_matrix_UB_12      -0.0123905000
_diffrn_orient_matrix_UB_13      0.0254481000
_diffrn_orient_matrix_UB_21      0.0086155000
_diffrn_orient_matrix_UB_22      0.0203068000
_diffrn_orient_matrix_UB_23      0.0157805000
_diffrn_orient_matrix_UB_31      -0.0878144000
_diffrn_orient_matrix_UB_32      0.0035126000
_diffrn_orient_matrix_UB_33      -0.0015829000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0968
_diffrn_reflns_av_unetI/netI     0.0959
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            67946
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.125
_diffrn_reflns_theta_min         2.207
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
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    1.299
_exptl_crystal_description       prism
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 1536 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         7630
_refine_ls_number_restraints     120
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0713
_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^)+(0.0864P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1664
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.895
_reflns_number_gt                4951
_reflns_number_total             7630
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01352a2.cif
_cod_data_source_block           SL
_cod_depositor_comments          'Adding full bibliography for 7131562.cif.'
_cod_database_code               7131562
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N00V-C4
 3.454 with sigma of 0.02
 N00V-C8
 3.514 with sigma of 0.02
 N009-C00N \\sim N0-C1
 with sigma of 0.02
 C00I-C00K \\sim C4-C2
 with sigma of 0.02
 C00I-C00Y \\sim C4-C6
 with sigma of 0.02
 C00I-C00Z \\sim C4-C0
 with sigma of 0.02
 C00K-C00N \\sim C2-C1
 with sigma of 0.02
 C00K-C00V \\sim C2-C5
 with sigma of 0.02
 C00N-C00R \\sim C1-C3
 with sigma of 0.02
 C00R-C00Y \\sim C3-C6
 with sigma of 0.02
 N00U-C012 \\sim N00V-C9
 with sigma of 0.02
 C00V-C011 \\sim C5-C7
 with sigma of 0.02
 C00Z-C010 \\sim C0-C8
 with sigma of 0.02
 C00Z-C012 \\sim C0-C9
 with sigma of 0.02
 C010-C011 \\sim C8-C7
 with sigma of 0.02
 N009-C00K \\sim N0-C2
 with sigma of 0.04
 N009-C00R \\sim N0-C3
 with sigma of 0.04
 C00I-C00N \\sim C4-C1
 with sigma of 0.04
 C00I-C00R \\sim C4-C3
 with sigma of 0.04
 C00I-C00V \\sim C4-C5
 with sigma of 0.04
 C00I-C010 \\sim C4-C8
 with sigma of 0.04
 C00I-C012 \\sim C4-C9
 with sigma of 0.04
 C00K-C00R \\sim C2-C3
 with sigma of 0.04
 C00K-C00Y \\sim C2-C6
 with sigma of 0.04
 C00K-C00Z \\sim C2-C0
 with sigma of 0.04
 C00K-C011 \\sim C2-C7
 with sigma of 0.04
 C00N-C00V \\sim C1-C5
 with sigma of 0.04
 C00N-C00Y \\sim C1-C6
 with sigma of 0.04
 N00U-C00Z \\sim N00V-C0
 with sigma of 0.04
 C00V-C010 \\sim C5-C8
 with sigma of 0.04
 C00Y-C00Z \\sim C6-C0
 with sigma of 0.04
 C00Z-C011 \\sim C0-C7
 with sigma of 0.04
 C010-C012 \\sim C8-C9
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C5 \\sim N0 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C6 \\sim C0 \\sim C7
\\sim C8 \\sim C9 \\sim N00V: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 1.7A
Uanis(N0) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 N00V, C9
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(N0)=Sof(H0A)=Sof(H0B)=Sof(H0C)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(C3)=Sof(H3A)=
 Sof(H3B)=Sof(C4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(C0)=Sof(C7)=
 Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(N00V)=1-FVAR(1)
 Sof(N009)=Sof(H00D)=Sof(H00G)=Sof(H00H)=Sof(C00I)=Sof(C00K)=Sof(C00N)=
 Sof(H00N)=Sof(C00R)=Sof(H00I)=Sof(H00J)=Sof(N00U)=Sof(C00V)=Sof(H00V)=
 Sof(C00Y)=Sof(H00K)=Sof(H00R)=Sof(C00Z)=Sof(C010)=Sof(H010)=Sof(C011)=
 Sof(H011)=Sof(C012)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00N(H00N), C1(H1)
6.b Secondary CH2 refined with riding coordinates:
 C00R(H00I,H00J), C00Y(H00K,H00R), C3(H3A,H3B), C6(H6A,H6B)
6.c Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00S(H00S),
 C00V(H00V), C00W(H00W), C010(H010), C011(H011), C013(H013), C5(H5), C7(H7),
 C8(H8)
6.d Idealised Me refined as rotating group:
 N009(H00D,H00G,H00H), C00X(H00A,H00B,H00C), C014(H01A,H01B,H01C), N0(H0A,H0B,
 H0C)
;
_shelx_res_checksum              46006
_shelx_hkl_checksum              23404
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.361
_oxdiff_exptl_absorpt_empirical_full_min 0.700