A selective cocrystallization separation method based on non-covalent interactions and its application
Wang, Na; Wang, Jingkang; Huang, Xin; Wang, Ting; Li, Xin; Yang, Jinyue; Bao, Ying; Yin, Qiuxiang; Hao, Hongxun; CrystEngComm 23 (2021) 1550–1554; doi:10.1039/D0CE01799J

data_7242217
_publ_section_title
;
 A selective cocrystallization separation method based on non-covalent
 interactions and its application
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              1550
_journal_page_last               1554
_journal_paper_doi               10.1039/D0CE01799J
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C7 H8 O, C H O2'
_chemical_formula_sum            'C8 H9 O3'
_chemical_formula_weight         153.15
_chemical_name_systematic        'p-cresol_oxalic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-22 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.229(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4483(6)
_cell_length_b                   6.0743(2)
_cell_length_c                   7.2533(2)
_cell_measurement_reflns_used    3567
_cell_measurement_temperature    160.00(10)
_cell_measurement_theta_max      74.5530
_cell_measurement_theta_min      2.5530
_cell_volume                     764.21(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (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      160.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.953
_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    -68.00  27.00   0.50    0.20    --  -45.62  75.00-119.00  190
  2  \w   -118.00 -23.00   0.50    0.20    --  -45.62 -75.00 113.00  190
  3  \w    -26.00  69.00   0.50    0.20    --   45.62 -75.00 113.00  190
  4  \w     23.00 119.00   0.50    0.20    --   45.62  75.00-119.00  192
  5  \w   -173.00 -77.00   0.50    0.80    -- -100.00 -75.00 113.00  192
  6  \w   -123.00 -27.00   0.50    0.80    -- -100.00  75.00-119.00  192
  7  \w     29.00 125.00   0.50    0.80    --  101.75 -75.00 113.00  192
  8  \w     79.00 175.00   0.50    0.80    --  101.75  75.00-119.00  192
  9  \w   -118.00 -73.00   0.50    0.20    --  -45.62-125.00 -90.00   90
 10  \w   -118.00 -73.00   0.50    0.20    --  -45.62-125.00-180.00   90
 11  \w   -175.00 -84.00   0.50    0.80    -- -100.00 -30.00  30.00  182
 12  \w   -172.00 -85.00   0.50    0.80    -- -100.00 -45.00 150.00  174
 13  \w   -118.00 -24.00   0.50    0.80    -- -100.00  15.00 -60.00  188
 14  \w     29.00 109.00   0.50    0.80    --  101.75 -94.00  30.00  160
 15  \w     29.00 109.00   0.50    0.80    --  101.75 -94.00 -30.00  160
 16  \w   -118.00 -29.00   0.50    0.20    --  -45.62 -57.00-180.00  178
 17  \w     22.00  59.00   0.50    0.20    --   45.62  77.00  30.00   74
 18  \w     30.00 119.00   0.50    0.20    --   45.62  57.00 -30.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0123867000
_diffrn_orient_matrix_UB_12      -0.2097433000
_diffrn_orient_matrix_UB_13      0.1189956000
_diffrn_orient_matrix_UB_21      -0.0846356000
_diffrn_orient_matrix_UB_22      0.0097980000
_diffrn_orient_matrix_UB_23      0.0418447000
_diffrn_orient_matrix_UB_31      -0.0239446000
_diffrn_orient_matrix_UB_32      -0.1421684000
_diffrn_orient_matrix_UB_33      -0.1724725000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6955
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.668
_diffrn_reflns_theta_min         2.547
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.857
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
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    1.331
_exptl_crystal_description       plate
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0444P)^2^+0.4207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1301
_reflns_number_total             1491
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01799j2.cif
_cod_data_source_block           pc_oxa_frxl
_cod_depositor_comments
'Adding full bibliography for 7242216--7242217.cif.'
_cod_database_code               7242217
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.847
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H7BD)=Sof(H7BE)=Sof(H7BF)=1-FVAR(1)
 Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=FVAR(1)
3.a Me refined with riding coordinates:
 C7(H7AA,H7AB,H7AC)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C1(H1A)
;
_shelx_res_checksum              95231
_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 2.091
_oxdiff_exptl_absorpt_empirical_full_min 0.546