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_7242216
_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         'C H4 N2 O, C7 H8 O'
_chemical_formula_sum            'C8 H12 N2 O2'
_chemical_formula_weight         168.20
_chemical_name_systematic        o-cresol_urea
_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                 93.9770(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.40010(10)
_cell_length_b                   26.1446(6)
_cell_length_c                   10.7253(2)
_cell_measurement_reflns_used    5457
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      76.1120
_cell_measurement_theta_min      3.3770
_cell_volume                     2070.06(7)
_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      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.945
_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   -119.00 -56.00   0.50    0.40    --  -46.50-159.00  47.00  126
  2  \w    -92.00 -16.00   0.50    0.40    --  -46.50 118.00 -73.00  152
  3  \w     50.00 120.00   0.50    0.40    --   46.50 159.00  79.00  140
  4  \w     10.00  92.00   0.50    0.40    --   46.50-118.00-159.00  164
  5  \w   -112.00 -27.00   0.50    1.60    -- -100.00 118.00 -73.00  170
  6  \w   -173.00 -84.00   0.50    1.60    -- -100.00-118.00-159.00  178
  7  \w     50.00 164.00   0.50    1.60    --  107.75 159.00  79.00  228
  8  \w     35.00 113.00   0.50    1.60    --  107.75-118.00-159.00  156
  9  \w     35.00 117.00   0.50    1.60    --  107.75-159.00  47.00  164
 10  \w    148.00 175.00   0.50    1.60    --  107.75 118.00 -73.00   54
 11  \w    -13.00  63.00   0.50    0.40    --   46.50 -57.00  60.00  152
 12  \w     31.00  64.00   0.50    0.40    --   46.50  57.00-150.00   66
 13  \w     89.00 117.00   0.50    0.40    --   46.50  57.00-150.00   56
 14  \w     73.00 120.00   0.50    0.40    --   46.50 125.00-120.00   94
 15  \w   -113.00 -52.00   0.50    1.60    -- -100.00  45.00 -30.00  122
 16  \w   -172.00 -87.00   0.50    1.60    -- -100.00 -45.00  30.00  170
 17  \w   -108.00 -49.00   0.50    1.60    -- -100.00  45.00 150.00  118
 18  \w     36.00  68.00   0.50    1.60    --  107.75 -61.00-180.00   64
 19  \w     36.00  89.00   0.50    1.60    --  107.75 -94.00 -30.00  106
 20  \w     68.00  94.00   0.50    1.60    --  107.75 -45.00 120.00   52
 21  \w     35.00  60.00   0.50    1.60    --  107.75 -45.00 120.00   50
 22  \w     98.00 172.00   0.50    1.60    --  107.75  30.00 -60.00  148
 23  \w     77.00 119.00   0.50    1.60    --  107.75 -61.00-180.00   84
;
_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      0.0219526000
_diffrn_orient_matrix_UB_12      -0.0260679000
_diffrn_orient_matrix_UB_13      0.1290636000
_diffrn_orient_matrix_UB_21      -0.0428507000
_diffrn_orient_matrix_UB_22      -0.0522090000
_diffrn_orient_matrix_UB_23      -0.0616910000
_diffrn_orient_matrix_UB_31      0.2029640000
_diffrn_orient_matrix_UB_32      -0.0082192000
_diffrn_orient_matrix_UB_33      -0.0167507000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20209
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.393
_diffrn_reflns_theta_min         3.381
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81756
_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    1.079
_exptl_crystal_description       irregular
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0517
_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^)+(0.1037P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1652
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2714
_reflns_number_total             4152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01799j2.cif
_cod_data_source_block           ocu_nosolvent
_cod_depositor_comments
'Adding full bibliography for 7242216--7242217.cif.'
_cod_database_code               7242216
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.968
_reflns_odcompleteness_completeness 99.97
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C8(H8), C11(H11), C9(H9), C5(H5), C3(H3), C4(H4A)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              10992
_shelx_fab_checksum              12429
_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 1.437
_oxdiff_exptl_absorpt_empirical_full_min 0.839