#------------------------------------------------------------------------------
#$Date: 2021-03-05 03:49:26 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262592 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/22/7242217.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7242217
loop_
_publ_author_name
'Wang, Na'
'Wang, Jingkang'
'Huang, Xin'
'Wang, Ting'
'Li, Xin'
'Yang, Jinyue'
'Bao, Ying'
'Yin, Qiuxiang'
'Hao, Hongxun'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  27.00   0.50    0.20    --  -45.62  75.00-119.00  190
  2  ω   -118.00 -23.00   0.50    0.20    --  -45.62 -75.00 113.00  190
  3  ω    -26.00  69.00   0.50    0.20    --   45.62 -75.00 113.00  190
  4  ω     23.00 119.00   0.50    0.20    --   45.62  75.00-119.00  192
  5  ω   -173.00 -77.00   0.50    0.80    -- -100.00 -75.00 113.00  192
  6  ω   -123.00 -27.00   0.50    0.80    -- -100.00  75.00-119.00  192
  7  ω     29.00 125.00   0.50    0.80    --  101.75 -75.00 113.00  192
  8  ω     79.00 175.00   0.50    0.80    --  101.75  75.00-119.00  192
  9  ω   -118.00 -73.00   0.50    0.20    --  -45.62-125.00 -90.00   90
 10  ω   -118.00 -73.00   0.50    0.20    --  -45.62-125.00-180.00   90
 11  ω   -175.00 -84.00   0.50    0.80    -- -100.00 -30.00  30.00  182
 12  ω   -172.00 -85.00   0.50    0.80    -- -100.00 -45.00 150.00  174
 13  ω   -118.00 -24.00   0.50    0.80    -- -100.00  15.00 -60.00  188
 14  ω     29.00 109.00   0.50    0.80    --  101.75 -94.00  30.00  160
 15  ω     29.00 109.00   0.50    0.80    --  101.75 -94.00 -30.00  160
 16  ω   -118.00 -29.00   0.50    0.20    --  -45.62 -57.00-180.00  178
 17  ω     22.00  59.00   0.50    0.20    --   45.62  77.00  30.00   74
 18  ω     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       'ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0444P)²+0.4207P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38740(6) 0.45083(17) 0.67107(15) 0.0250(3) Uani 1 1 d . . . . .
O2 O 0.47829(6) 0.72216(16) 0.51339(15) 0.0241(3) Uani 1 1 d . . . . .
O3 O 0.41990(6) 1.01541(16) 0.62478(15) 0.0243(3) Uani 1 1 d . . . . .
C8 C 0.46942(8) 0.9324(2) 0.54276(19) 0.0191(3) Uani 1 1 d . . . . .
C3 C 0.31067(8) 0.4722(2) 0.70246(19) 0.0206(3) Uani 1 1 d . . . . .
C2 C 0.25752(9) 0.3064(2) 0.6596(2) 0.0256(4) Uani 1 1 d . . . . .
H2 H 0.272372 0.175166 0.607886 0.031 Uiso 1 1 calc R . . . .
C4 C 0.28858(9) 0.6688(2) 0.7793(2) 0.0235(3) Uani 1 1 d . . . . .
H4 H 0.324433 0.780307 0.807637 0.028 Uiso 1 1 calc R . . . .
C6 C 0.15776(9) 0.5328(3) 0.7719(2) 0.0286(4) Uani 1 1 d . . . . .
C5 C 0.21255(9) 0.6968(3) 0.8131(2) 0.0258(4) Uani 1 1 d . . . . .
H5 H 0.197817 0.828302 0.864646 0.031 Uiso 1 1 calc R . . . .
C1 C 0.18173(9) 0.3382(3) 0.6946(2) 0.0298(4) Uani 1 1 d . . . . .
H1A H 0.145988 0.226462 0.665756 0.036 Uiso 1 1 calc R . . . .
C7 C 0.07529(11) 0.5648(4) 0.8116(3) 0.0449(5) Uani 1 1 d . . . . .
H7AA H 0.045848 0.435650 0.774481 0.067 Uiso 0.41(4) 1 calc R . P A 1
H7AB H 0.073938 0.589277 0.941966 0.067 Uiso 0.41(4) 1 calc R . P A 1
H7AC H 0.053655 0.689744 0.743588 0.067 Uiso 0.41(4) 1 calc R . P A 1
H1 H 0.3983(13) 0.312(4) 0.649(3) 0.053(7) Uiso 1 1 d . . . . .
H2A H 0.4404(13) 0.633(4) 0.564(3) 0.061(7) Uiso 1 1 d . . . . .
H7BD H 0.069(2) 0.719(7) 0.876(5) 0.051(12) Uiso 0.59(4) 1 d . . P A 2
H7BE H 0.058(2) 0.433(6) 0.885(5) 0.045(11) Uiso 0.59(4) 1 d . . P A 2
H7BF H 0.034(2) 0.554(6) 0.701(5) 0.044(11) Uiso 0.59(4) 1 d . . P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 110.4(15) . . ?
C8 O2 H2A 112.9(14) . . ?
O2 C8 C8 111.01(15) . 3_676 ?
O3 C8 O2 126.21(13) . . ?
O3 C8 C8 122.78(16) . 3_676 ?
O1 C3 C4 117.43(13) . . ?
C2 C3 O1 122.06(13) . . ?
C2 C3 C4 120.51(14) . . ?
C3 C2 H2 120.4 . . ?
C3 C2 C1 119.19(14) . . ?
C1 C2 H2 120.4 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.29(14) . . ?
C5 C4 H4 120.4 . . ?
C5 C6 C1 117.73(14) . . ?
C5 C6 C7 120.93(16) . . ?
C1 C6 C7 121.34(16) . . ?
C4 C5 C6 121.54(14) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C2 C1 C6 121.73(15) . . ?
C2 C1 H1A 119.1 . . ?
C6 C1 H1A 119.1 . . ?
C6 C7 H7AA 109.5 . . ?
C6 C7 H7AB 109.5 . . ?
C6 C7 H7AC 109.5 . . ?
C6 C7 H7BD 110(2) . . ?
C6 C7 H7BE 110.2(19) . . ?
C6 C7 H7BF 116.7(19) . . ?
H7AA C7 H7AB 109.5 . . ?
H7AA C7 H7AC 109.5 . . ?
H7AB C7 H7AC 109.5 . . ?
H7BD C7 H7BE 114(3) . . ?
H7BD C7 H7BF 108(3) . . ?
H7BE C7 H7BF 97(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3881(17) . ?
O1 H1 0.88(3) . ?
O2 C8 1.3064(17) . ?
O2 H2A 0.96(3) . ?
O3 C8 1.2110(18) . ?
C8 C8 1.530(3) 3_676 ?
C3 C2 1.381(2) . ?
C3 C4 1.390(2) . ?
C2 H2 0.9300 . ?
C2 C1 1.387(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(2) . ?
C6 C5 1.390(2) . ?
C6 C1 1.392(2) . ?
C6 C7 1.510(2) . ?
C5 H5 0.9300 . ?
C1 H1A 0.9300 . ?
C7 H7AA 0.9600 . ?
C7 H7AB 0.9600 . ?
C7 H7AC 0.9600 . ?
C7 H7BD 1.06(4) . ?
C7 H7BE 1.03(4) . ?
C7 H7BF 1.02(4) . ?
