Solvatomorphism and first-time observation of acid–acid catemer in 4-phenylamino-benzoic acids
Liu, Xiaoting; Cui, Jingliang; Zeng, Qun; Fang, Liwen; Liang, Peng-Yu; Zhou, Pan-Pan; Parkin, Sean; Li, Tonglei; Ruan, Shigang; Long, Sihui; RSC Advances 13 (2023) 21021–21035; doi:10.1039/D3RA04102F

data_7247079
_publ_section_title
;
 Solvatomorphism and first-time observation of acid--acid catemer in
 4-phenylamino-benzoic acids
;
_journal_issue                   30
_journal_name_full               'RSC Advances'
_journal_page_first              21021
_journal_page_last               21035
_journal_paper_doi               10.1039/D3RA04102F
_journal_volume                  13
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.9720(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.71260(10)
_cell_length_b                   6.04470(10)
_cell_length_c                   10.84520(10)
_cell_measurement_reflns_used    6748
_cell_measurement_temperature    302.98(10)
_cell_measurement_theta_max      75.7170
_cell_measurement_theta_min      4.0680
_cell_volume                     570.825(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.962
_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     43.00  71.00   0.50    0.05    --  104.25 -61.00  60.00   56
  2  \w     35.00  70.00   0.50    0.05    --  104.25 -61.00 -90.00   70
  3  \w     45.00  70.00   0.50    0.05    --  104.25 -61.00-150.00   50
  4  \w     45.00  73.00   0.50    0.05    --  104.25 -61.00-180.00   56
  5  \w     60.00 139.00   0.50    0.05    --  104.25  -2.00-152.00  158
  6  \w     47.00  72.00   0.50    0.05    --   46.32   2.00  27.00   50
  7  \w     13.00  38.00   0.50    0.05    --   46.32  -2.00-152.00   50
  8  \w     36.00  69.00   0.50    0.05    --  104.25 -94.00-180.00   66
  9  \w     41.00  70.00   0.50    0.05    --  104.25-125.00-150.00   58
 10  \w     81.00 109.00   0.50    0.05    --  104.25-125.00-150.00   56
 11  \w     81.00 106.00   0.50    0.05    --  104.25 -94.00-180.00   50
 12  \w     36.00  81.00   0.50    0.05    --   46.32-125.00  30.00   90
 13  \w     33.00  61.00   0.50    0.05    --  104.25-106.00  40.50   56
 14  \w     83.00 108.00   0.50    0.05    --  104.25-106.00  40.50   50
 15  \w    -61.00 -23.00   0.50    0.05    --  -46.32   2.00  27.00   76
 16  \w   -112.00 -65.00   0.50    0.05    --  -46.32   2.00  27.00   94
 17  \w   -174.00 -29.00   0.50    0.05    -- -102.00   2.00  27.00  290
 18  \w    -72.00 -46.00   0.50    0.05    -- -102.00  77.00 150.00   52
 19  \w   -101.00 -74.00   0.50    0.05    -- -102.00  77.00 150.00   54
 20  \w   -111.00 -82.00   0.50    0.05    -- -102.00 125.00  90.00   58
 21  \w    -71.00 -45.00   0.50    0.05    -- -102.00 125.00  90.00   52
 22  \w    -78.00 -35.00   0.50    0.05    --  -46.32 -37.00 -30.00   86
 23  \w   -119.00 -83.00   0.50    0.05    --  -46.32 -37.00 -30.00   72
 24  \w     66.00  93.00   0.50    0.05    --   46.32  57.00-150.00   54
 25  \w     -6.00  23.00   0.50    0.05    --  -46.32  19.00 -60.00   58
 26  \w     34.00  81.00   0.50    0.05    --   46.32  57.00-180.00   94
 27  \w     24.00  71.00   0.50    0.05    --   46.32  77.00  90.00   94
 28  \w     37.00  64.00   0.50    0.05    --   46.32  37.00 -60.00   54
 29  \w     13.00  55.00   0.50    0.05    --   46.32 -57.00-180.00   84
 30  \w     25.00  51.00   0.50    0.05    --   46.32  77.00-180.00   52
 31  \w     31.00  60.00   0.50    0.05    --   46.32  77.00  30.00   58
 32  \w     33.00  58.00   0.50    0.05    --   46.32  57.00 -90.00   50
 33  \w     37.00  67.00   0.50    0.05    --   46.32  19.00-150.00   60
 34  \w     24.00  50.00   0.50    0.05    --   46.32  77.00 -30.00   52
 35  \w   -106.00 -80.00   0.50    0.05    -- -102.00 -77.00 -90.00   52
 36  \w   -108.00 -82.00   0.50    0.05    -- -102.00 -77.00 150.00   52
 37  \w   -174.00-147.00   0.50    0.05    -- -102.00 -77.00-150.00   54
 38  \w   -104.00 -79.00   0.50    0.05    -- -102.00 -77.00 120.00   50
 39  \w   -172.00-146.00   0.50    0.05    -- -102.00 -77.00 150.00   52
 40  \w   -108.00 -82.00   0.50    0.05    -- -102.00 -70.00  76.75   52
 41  \w   -106.00 -80.00   0.50    0.05    -- -102.00 -80.00  58.09   52
 42  \w   -115.00 -89.00   0.50    0.05    -- -102.00 -45.00   0.00   52
 43  \w   -107.00 -82.00   0.50    0.05    -- -102.00 -70.00  96.50   50
 44  \w   -173.00-142.00   0.50    0.05    -- -102.00 -70.00  76.75   62
 45  \w   -111.00 -85.00   0.50    0.05    -- -102.00 -61.00 150.00   52
 46  \w   -110.00 -85.00   0.50    0.05    -- -102.00 -61.00  30.00   50
 47  \w   -115.00 -89.00   0.50    0.05    -- -102.00 -45.00 120.00   52
 48  \w   -115.00 -89.00   0.50    0.05    -- -102.00 -61.00-180.00   52
 49  \w   -112.00 -87.00   0.50    0.05    -- -102.00 -55.00 157.48   50
 50  \w   -114.00 -88.00   0.50    0.05    -- -102.00 -56.00-138.31   52
 51  \w   -106.00 -80.00   0.50    0.05    -- -102.00 -80.00  70.36   52
 52  \w   -166.00-140.00   0.50    0.05    -- -102.00 -77.00 120.00   52
 53  \w   -104.00 -79.00   0.50    0.05    -- -102.00 -77.00-150.00   50
 54  \w   -158.00-133.00   0.50    0.05    -- -102.00 -77.00-180.00   50
 55  \w   -104.00 -79.00   0.50    0.05    -- -102.00 -77.00-180.00   50
 56  \w   -110.00 -85.00   0.50    0.05    -- -102.00 -61.00 120.00   50
 57  \w     82.00 108.00   0.50    0.05    --  104.25  77.00 150.00   52
 58  \w     86.00 111.00   0.50    0.05    --  104.25  77.00  90.00   50
 59  \w     90.00 117.00   0.50    0.05    --  104.25  61.00-150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1767496000
_diffrn_orient_matrix_UB_12      0.0038824000
_diffrn_orient_matrix_UB_13      0.0107637000
_diffrn_orient_matrix_UB_21      -0.0072322000
_diffrn_orient_matrix_UB_22      -0.0060763000
_diffrn_orient_matrix_UB_23      0.1416795000
_diffrn_orient_matrix_UB_31      0.0028535000
_diffrn_orient_matrix_UB_32      -0.2547831000
_diffrn_orient_matrix_UB_33      -0.0032204000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7376
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.818
_diffrn_reflns_theta_min         4.079
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 843 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2113
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0410P)^2^+0.0775P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0775
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.855
_reflns_Friedel_fraction_max     0.793
_reflns_number_gt                2097
_reflns_number_total             2113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra04102f2.cif
_cod_data_source_block           2
_cod_database_code               7247079
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 98.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              24367
_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 1.870
_oxdiff_exptl_absorpt_empirical_full_min 0.587