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_7247084
_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         'C16 H17 N O2, C5 H5 N'
_chemical_formula_sum            'C21 H22 N2 O2'
_chemical_formula_weight         334.40
_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             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                85.239(4)
_cell_angle_beta                 74.568(5)
_cell_angle_gamma                73.318(5)
_cell_formula_units_Z            2
_cell_length_a                   8.0697(5)
_cell_length_b                   8.4048(4)
_cell_length_c                   14.8801(6)
_cell_measurement_reflns_used    4831
_cell_measurement_temperature    303.99(10)
_cell_measurement_theta_max      75.8380
_cell_measurement_theta_min      3.0500
_cell_volume                     931.88(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (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      303.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.955
_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    141.00 172.00   1.00    0.50    --  104.25  66.00 143.00   31
  2  \w    124.00 160.00   1.00    0.50    --  104.25  45.00  90.00   36
  3  \w    106.00 175.00   1.00    0.50    --  104.25  77.00  30.00   69
  4  \w     88.00 174.00   1.00    0.50    --  104.25  61.00  60.00   86
  5  \w     74.00  99.00   1.00    0.10    --   46.57  66.00 143.00   25
  6  \w    -95.00 -29.00   1.00    0.50    -- -102.00  77.00 -30.00   66
  7  \w    -64.00 -39.00   1.00    0.50    -- -102.00  61.00 -30.00   25
  8  \w    -54.00  24.00   1.00    0.10    --  -46.57  66.00 143.00   78
  9  \w    -75.00 -41.00   1.00    0.50    -- -102.00  66.00 143.00   34
 10  \w    -67.00 -29.00   1.00    0.50    -- -102.00  61.00 120.00   38
 11  \w    -68.00 -40.00   1.00    0.50    -- -102.00  61.00  90.00   28
 12  \w   -175.00 -84.00   1.00    0.50    -- -102.00 -66.00   7.00   91
 13  \w   -119.00 -74.00   1.00    0.10    --  -46.57-125.00  90.00   45
 14  \w    -91.00 -66.00   1.00    0.10    --  -46.57 -66.00   7.00   25
 15  \w   -115.00 -78.00   1.00    0.10    --  -46.57-125.00-180.00   37
 16  \w     32.00  58.00   1.00    0.50    --  104.25 -77.00 -90.00   26
 17  \w     71.00 108.00   1.00    0.50    --  104.25 -77.00 -90.00   37
 18  \w     40.00  66.00   1.00    0.50    --  104.25 -66.00   7.00   26
 19  \w    -18.00   9.00   1.00    0.10    --   46.57 -66.00   7.00   27
 20  \w     13.00  63.00   1.00    0.10    --   46.57 -66.00   7.00   50
 21  \w     32.00  57.00   1.00    0.50    --  104.25 -61.00 120.00   25
 22  \w     37.00  62.00   1.00    0.50    --  104.25 -61.00 150.00   25
 23  \w    -13.00  14.00   1.00    0.10    --   46.32 -66.00   7.00   27
 24  \w    -17.00  13.00   1.00    0.10    --  -46.32  19.00-180.00   30
 25  \w    -24.00  21.00   1.00    0.10    --  -46.32  37.00  90.00   45
 26  \w    -16.00  23.00   1.00    0.10    --  -46.32  19.00  30.00   39
 27  \w     35.00  64.00   1.00    0.10    --   46.32-125.00   0.00   29
 28  \w     66.00  91.00   1.00    0.10    --   46.32-125.00   0.00   25
 29  \w   -123.00 -97.00   1.00    0.50    -- -102.00 -45.00 -30.00   26
 30  \w    -73.00 -38.00   1.00    0.50    -- -102.00 125.00  90.00   35
 31  \w   -160.00-125.00   1.00    0.50    -- -102.00 -45.00 -30.00   35
 32  \w   -125.00 -72.00   1.00    0.50    -- -102.00 143.00  92.22   53
 33  \w   -110.00 -79.00   1.00    0.50    -- -102.00 125.00  90.00   31
 34  \w   -126.00 -94.00   1.00    0.50    -- -102.00 144.00-168.76   32
 35  \w     78.00 111.00   1.00    0.50    --  104.25-125.00 -60.00   33
 36  \w     43.00  69.00   1.00    0.50    --  104.25-125.00 -60.00   26
 37  \w     34.00  90.00   1.00    0.50    --  104.25-125.00 -90.00   56
 38  \w     87.00 112.00   1.00    0.50    --  104.25-125.00-150.00   25
 39  \w     55.00  84.00   1.00    0.50    --  104.25 -94.00   0.00   29
 40  \w     90.00 170.00   1.00    0.50    --  104.25 125.00 -60.00   80
 41  \w     92.00 173.00   1.00    0.50    --  104.25  45.00-180.00   81
 42  \w    137.00 175.00   1.00    0.50    --  104.25  45.00   0.00   38
 43  \w     49.00  75.00   1.00    0.50    --  104.25 -94.00  90.00   26
 44  \w     79.00 111.00   1.00    0.50    --  104.25-125.00  90.00   32
 45  \w     52.00  78.00   1.00    0.50    --  104.25-125.00  90.00   26
 46  \w     74.00 115.00   1.00    0.50    --  104.25-132.00  70.63   41
 47  \w     41.00  66.00   1.00    0.50    --  104.25-125.00-150.00   25
 48  \w     33.00  67.00   1.00    0.50    --  104.25 -61.00-180.00   34
;
_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      -0.1485009000
_diffrn_orient_matrix_UB_12      0.1462541000
_diffrn_orient_matrix_UB_13      -0.0233806000
_diffrn_orient_matrix_UB_21      -0.0137738000
_diffrn_orient_matrix_UB_22      -0.1041344000
_diffrn_orient_matrix_UB_23      -0.0767844000
_diffrn_orient_matrix_UB_31      -0.1421622000
_diffrn_orient_matrix_UB_32      -0.0661886000
_diffrn_orient_matrix_UB_33      0.0713680000
_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  0.0380
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12119
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.453
_diffrn_reflns_theta_min         3.081
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (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    1.192
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0079(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   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0664P)^2^+0.0646P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1417
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2753
_reflns_number_total             3742
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra04102f2.cif
_cod_data_source_block           lsh_14_auto
_cod_database_code               7247084
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.914
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C12(H12), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              19787
_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 2.292
_oxdiff_exptl_absorpt_empirical_full_min 0.411