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_7247081
_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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 98.919(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5689(6)
_cell_length_b                   5.8946(2)
_cell_length_c                   14.9692(8)
_cell_measurement_reflns_used    3414
_cell_measurement_temperature    302.98(10)
_cell_measurement_theta_max      76.2460
_cell_measurement_theta_min      4.0800
_cell_volume                     1182.81(9)
_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  (Sheldrick, 2015)'
_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 0.990
_diffrn_measured_fraction_theta_max 0.937
_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     25.00 118.00   0.50    0.05    --   46.07  77.00-150.00  186
  2  \w     70.00 105.00   0.50    0.05    --   46.07 151.00  20.00   70
  3  \w    111.00 137.00   0.50    0.14    --  104.25 122.00-140.00   52
  4  \w     91.00 174.00   0.50    0.14    --  104.25  61.00-150.00  166
  5  \w     33.00  62.00   0.50    0.14    --  104.25 -61.00 -90.00   58
  6  \w     34.00 101.00   0.50    0.14    --  104.25 -94.00 -30.00  134
  7  \w     82.00 112.00   0.50    0.14    --  104.25-125.00-120.00   60
  8  \w     32.00 129.00   0.50    0.14    --  104.25-151.00 -23.00  194
  9  \w     53.00  90.00   0.50    0.05    --   46.07-122.00 137.00   74
 10  \w     68.00 105.00   0.50    0.14    --  104.25-122.00 137.00   74
 11  \w     39.00 106.00   0.50    0.14    --  104.25 -94.00 120.00  134
 12  \w    -23.00  29.00   0.50    0.05    --  -46.07  19.00 -90.00  104
 13  \w    -68.00 -34.00   0.50    0.14    -- -102.00  61.00-180.00   68
 14  \w    -76.00 -51.00   0.50    0.05    --  -46.07 122.00-140.00   50
 15  \w    -63.00 -37.00   0.50    0.14    -- -102.00  61.00  30.00   52
 16  \w    -66.00 -38.00   0.50    0.14    -- -102.00  61.00  60.00   56
 17  \w   -117.00 -91.00   0.50    0.14    -- -102.00 -30.00  30.00   52
 18  \w   -174.00-139.00   0.50    0.14    -- -102.00 -30.00  30.00   70
 19  \w   -150.00-125.00   0.50    0.14    -- -102.00-122.00 137.00   50
 20  \w   -164.00 -80.00   0.50    0.14    -- -102.00 -77.00  60.00  168
 21  \w   -118.00 -57.00   0.50    0.05    --  -46.07-151.00 -23.00  122
;
_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      -0.0122328000
_diffrn_orient_matrix_UB_12      0.2598183000
_diffrn_orient_matrix_UB_13      -0.0040459000
_diffrn_orient_matrix_UB_21      -0.0504485000
_diffrn_orient_matrix_UB_22      -0.0066350000
_diffrn_orient_matrix_UB_23      0.0853320000
_diffrn_orient_matrix_UB_31      0.1025068000
_diffrn_orient_matrix_UB_32      0.0273611000
_diffrn_orient_matrix_UB_33      0.0596790000
_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  0.0339
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6940
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.409
_diffrn_reflns_theta_min         4.093
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46601
_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 dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0032(12)
_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   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0912P)^2^+0.1056P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1678
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1719
_reflns_number_total             2334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra04102f2.cif
_cod_data_source_block           3
_cod_database_code               7247081
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 98.93
_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), C2(H2), 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              49253
_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 2.102
_oxdiff_exptl_absorpt_empirical_full_min 0.511