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_7247078
_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         'C13 H11 N O2'
_chemical_formula_sum            'C13 H11 N O2'
_chemical_formula_weight         213.23
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-27
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-06-29 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.167(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8122(6)
_cell_length_b                   29.731(3)
_cell_length_c                   6.4123(7)
_cell_measurement_reflns_used    2394
_cell_measurement_temperature    294.9(5)
_cell_measurement_theta_max      75.2390
_cell_measurement_theta_min      2.9950
_cell_volume                     1064.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.77a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.77a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.77a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.9(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.922
_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     32.00  71.00   1.50    2.00    --  104.25 -61.00 120.00   26
  2  \w     32.00  66.50   1.50    2.00    --  104.25 -61.00  90.00   23
  3  \w    -28.00  29.00   1.50    1.00    --   46.32 -19.00   0.00   38
  4  \w    -24.00   1.50   1.50    1.00    --   46.32 -19.00 -90.00   17
  5  \w     33.00  99.00   1.50    2.00    --  104.25 -94.00 -60.00   44
  6  \w     44.00  69.50   1.50    1.00    --   46.32-146.00 108.00   17
  7  \w     81.00 120.00   1.50    2.00    --  104.25-146.00 108.00   26
  8  \w     45.00  72.00   1.50    2.00    --  104.25-146.00 108.00   18
  9  \w     55.00  82.00   1.50    1.00    --   46.32-124.00 -85.00   18
 10  \w     44.00 110.00   1.50    2.00    --  104.25-124.00 -85.00   44
 11  \w    139.00 172.00   1.50    2.00    --  104.25  45.00 -90.00   22
 12  \w     95.00 120.50   1.50    2.00    --  104.25  45.00 -90.00   17
 13  \w    102.00 127.50   1.50    2.00    --  104.25 124.00  -6.00   17
 14  \w     66.00 114.00   1.50    1.00    --   46.32 146.00 158.00   32
 15  \w    -25.00  29.00   1.50    1.00    --  -46.32  19.00  30.00   36
 16  \w    -55.00 -29.50   1.50    2.00    -- -102.00  61.00  30.00   17
 17  \w    -67.00 -31.00   1.50    2.00    -- -102.00  77.00   0.00   24
 18  \w   -104.00 -71.00   1.50    2.00    -- -102.00  77.00   0.00   22
 19  \w   -103.00 -76.00   1.50    2.00    -- -102.00 146.00 158.00   18
 20  \w    -76.00 -49.00   1.50    1.00    --  -46.32 124.00  -6.00   18
 21  \w   -138.00-112.50   1.50    2.00    -- -102.00-146.00 108.00   17
 22  \w   -108.00 -69.00   1.50    1.00    --  -46.32-146.00 108.00   26
 23  \w   -164.00 -86.00   1.50    2.00    -- -102.00 -61.00  90.00   52
 24  \w   -148.00-121.00   1.50    2.00    -- -102.00-124.00 -85.00   18
 25  \w   -161.00 -89.00   1.50    2.00    -- -102.00 -45.00-180.00   48
;
_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      0.1327821000
_diffrn_orient_matrix_UB_12      -0.0357087000
_diffrn_orient_matrix_UB_13      -0.0970104000
_diffrn_orient_matrix_UB_21      0.1026479000
_diffrn_orient_matrix_UB_22      0.0373578000
_diffrn_orient_matrix_UB_23      -0.1146283000
_diffrn_orient_matrix_UB_31      0.2187809000
_diffrn_orient_matrix_UB_32      0.0040874000
_diffrn_orient_matrix_UB_33      0.2000750000
_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  0.0629
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6951
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.767
_diffrn_reflns_theta_min         2.973
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.77a (Rigaku Oxford Diffraction, 2022)
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    1.331
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0059(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0719P)^2^+0.0670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1494
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1464
_reflns_number_total             2102
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra04102f2.cif
_cod_data_source_block           1-I
_cod_database_code               7247078
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.910
_shelx_estimated_absorpt_t_min   0.879
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
;
_shelx_res_checksum              41821
_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 3.170
_oxdiff_exptl_absorpt_empirical_full_min 0.254