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_7247083
_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, C5 H5 N'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_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             2022-06-01
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.056(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2172(2)
_cell_length_b                   11.5108(3)
_cell_length_c                   16.6802(5)
_cell_measurement_reflns_used    6961
_cell_measurement_temperature    282(20)
_cell_measurement_theta_max      77.2730
_cell_measurement_theta_min      3.8580
_cell_volume                     1571.58(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      282(20)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.940
_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     99.00 132.00   0.50    0.05    --  107.75  19.00  30.00   66
  2  \w     99.00 175.00   0.50    0.05    --  107.75  19.00 150.00  152
  3  \w     32.00 112.00   0.50    0.05    --   47.57  10.00-117.00  160
  4  \w     99.00 145.00   0.50    0.05    --  107.75  10.00-117.00   92
  5  \w     35.00  63.00   0.50    0.05    --  107.75 -57.00  60.00   56
  6  \w    -14.00  20.00   0.50    0.05    --   47.57 -19.00 -90.00   68
  7  \w     35.00  63.00   0.50    0.05    --  107.75 -57.00  30.00   56
  8  \w    -26.00   0.00   0.50    0.05    --   47.57 -10.00  69.00   52
  9  \w     35.00  60.00   0.50    0.05    --  107.75 -57.00 150.00   50
 10  \w     61.00 111.00   0.50    0.05    --  107.75-125.00  60.00  100
 11  \w     82.00 112.00   0.50    0.05    --  107.75-125.00   0.00   60
 12  \w     51.00  76.00   0.50    0.05    --  107.75-125.00   0.00   50
 13  \w     72.00  97.00   0.50    0.05    --  107.75 -99.00 -90.00   50
 14  \w    -25.00   0.00   0.50    0.05    --  -47.57  10.00-117.00   50
 15  \w    -68.00 -32.00   0.50    0.05    -- -100.00  57.00-150.00   72
 16  \w   -108.00 -39.00   0.50    0.05    -- -100.00  77.00  30.00  138
 17  \w    -69.00 -29.00   0.50    0.05    -- -100.00  57.00  60.00   80
 18  \w    -64.00 -34.00   0.50    0.05    -- -100.00  57.00  90.00   60
 19  \w    -55.00 -29.00   0.50    0.05    -- -100.00  57.00 150.00   52
 20  \w   -106.00 -35.00   0.50    0.05    -- -100.00  77.00 150.00  142
 21  \w    -92.00 -29.00   0.50    0.05    --  -47.57 125.00  60.00  126
 22  \w   -107.00 -32.00   0.50    0.05    --  -47.57 -10.00  69.00  150
 23  \w   -148.00 -91.00   0.50    0.05    -- -100.00 -10.00  69.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0590845000
_diffrn_orient_matrix_UB_12      -0.0178601000
_diffrn_orient_matrix_UB_13      0.0842193000
_diffrn_orient_matrix_UB_21      -0.1787941000
_diffrn_orient_matrix_UB_22      0.0079836000
_diffrn_orient_matrix_UB_23      -0.0361742000
_diffrn_orient_matrix_UB_31      -0.0028260000
_diffrn_orient_matrix_UB_32      -0.1324327000
_diffrn_orient_matrix_UB_33      -0.0134243000
_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  0.0391
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10427
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.495
_diffrn_reflns_theta_min         4.673
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (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    1.235
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0084(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0645P)^2^+0.1339P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2563
_reflns_number_total             3138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra04102f2.cif
_cod_data_source_block           1-S
_cod_original_cell_volume        1571.59(8)
_cod_database_code               7247083
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.908
_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 O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
  C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              66916
_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 2.021
_oxdiff_exptl_absorpt_empirical_full_min 0.601