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_7247080
_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_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_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                80.106(4)
_cell_angle_beta                 85.810(3)
_cell_angle_gamma                73.682(4)
_cell_formula_units_Z            2
_cell_length_a                   5.8469(2)
_cell_length_b                   6.4881(3)
_cell_length_c                   15.9753(7)
_cell_measurement_reflns_used    3784
_cell_measurement_temperature    302.99(10)
_cell_measurement_theta_max      75.5690
_cell_measurement_theta_min      5.6100
_cell_volume                     572.77(4)
_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      302.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.936
_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     33.00  91.00   0.50    0.05    --   46.32  62.00 100.00  116
  2  \w     89.00 174.00   0.50    0.05    --  104.25  62.00 100.00  170
  3  \w    136.00 177.00   0.50    0.05    --  104.25  15.00  30.00   82
  4  \w     91.00 128.00   0.50    0.05    --  104.25  15.00  30.00   74
  5  \w    110.00 175.00   0.50    0.05    --  104.25  45.00-120.00  130
  6  \w    -24.00  29.00   0.50    0.05    --  -46.32  19.00  30.00  106
  7  \w    -62.00 -28.00   0.50    0.05    --  -46.32  62.00 100.00   68
  8  \w    -19.00   6.00   0.50    0.05    --  -46.32  62.00 100.00   50
  9  \w    -22.00   6.00   0.50    0.05    --   46.32 -62.00 -37.00   56
 10  \w    -28.00  29.00   0.50    0.05    --   46.32 -19.00-180.00  114
 11  \w     19.00  49.00   0.50    0.05    --   46.32 -62.00 -37.00   60
 12  \w     59.00 103.00   0.50    0.05    --  104.25 -77.00-120.00   88
 13  \w     41.00  66.00   0.50    0.05    --  104.25 -62.00 -37.00   50
 14  \w     77.00 103.00   0.50    0.05    --  104.25 -77.00  60.00   52
 15  \w     34.00  65.00   0.50    0.05    --  104.25 -61.00 120.00   62
 16  \w     33.00  58.00   0.50    0.05    --  104.25 -61.00  90.00   50
 17  \w     33.00  70.00   0.50    0.05    --  104.25 -77.00  60.00   74
 18  \w     32.00  76.00   0.50    0.05    --  104.25 -94.00  30.00   88
 19  \w     70.00  95.00   0.50    0.05    --  104.25 -94.00  60.00   50
 20  \w     87.00 112.00   0.50    0.05    --  104.25-125.00 -30.00   50
 21  \w     44.00  89.00   0.50    0.05    --  104.25 -94.00 -30.00   90
 22  \w     32.00  64.00   0.50    0.05    --  104.25-125.00 -30.00   64
 23  \w     40.00  65.00   0.50    0.05    --  104.25-125.00 -60.00   50
 24  \w     69.00 104.00   0.50    0.05    --  104.25-125.00 -60.00   70
 25  \w   -124.00 -87.00   0.50    0.05    -- -102.00 142.00  -8.68   74
 26  \w    -70.00 -36.00   0.50    0.05    -- -102.00  62.00 100.00   68
 27  \w    -62.00 -29.00   0.50    0.05    -- -102.00 125.00 120.00   66
 28  \w   -112.00 -79.00   0.50    0.05    -- -102.00 125.00 150.00   66
 29  \w    -64.00 -34.00   0.50    0.05    -- -102.00  61.00 -90.00   60
 30  \w    -69.00 -44.00   0.50    0.05    -- -102.00  61.00-150.00   50
 31  \w   -117.00 -78.00   0.50    0.05    --  -46.32 -62.00 -37.00   78
 32  \w    -72.00 -32.00   0.50    0.05    --  -46.32 -62.00 -37.00   80
 33  \w   -120.00 -94.00   0.50    0.05    -- -102.00 -62.00 -37.00   52
 34  \w   -160.00-134.00   0.50    0.05    -- -102.00 -62.00 -37.00   52
 35  \w   -175.00-141.00   0.50    0.05    -- -102.00 -30.00  30.00   68
 36  \w   -133.00 -94.00   0.50    0.05    -- -102.00 -30.00  30.00   78
 37  \w   -106.00 -81.00   0.50    0.05    --  -46.32-125.00  90.00   50
 38  \w   -174.00-102.00   0.50    0.05    -- -102.00-125.00  90.00  144
;
_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      0.1330325000
_diffrn_orient_matrix_UB_12      0.1435919000
_diffrn_orient_matrix_UB_13      -0.0595854000
_diffrn_orient_matrix_UB_21      -0.2395204000
_diffrn_orient_matrix_UB_22      0.1468909000
_diffrn_orient_matrix_UB_23      -0.0356158000
_diffrn_orient_matrix_UB_31      -0.0189501000
_diffrn_orient_matrix_UB_32      0.1434763000
_diffrn_orient_matrix_UB_33      0.0690657000
_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  0.0264
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5721
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.268
_diffrn_reflns_theta_min         5.624
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49211
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2255
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0775P)^2^+0.0528P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1350
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1950
_reflns_number_total             2255
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra04102f2.cif
_cod_data_source_block           4
_cod_database_code               7247080
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.925
_reflns_odcompleteness_completeness 99.36
_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
2. Restrained distances
 O1-H1
 0.86 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C12(H12), C13(H13), C9(H9), C10(H10), C2(H2), C6(H6), C3(H3), C5(H5)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              26595
_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 2.406
_oxdiff_exptl_absorpt_empirical_full_min 0.258