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_7247087
_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'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-04-09
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.8907(15)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8309(2)
_cell_length_b                   16.98433(19)
_cell_length_c                   11.30860(15)
_cell_measurement_reflns_used    13270
_cell_measurement_temperature    287.3(3)
_cell_measurement_theta_max      75.9220
_cell_measurement_theta_min      2.6080
_cell_volume                     2876.85(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 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      287.3(3)
_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 0.946
_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     49.00  75.00   0.50    0.05    --   47.57  54.00  91.00   52
  2  \w     83.00 111.00   0.50    0.05    --   47.57  54.00  91.00   56
  3  \w     97.00 175.00   0.50    0.07    --  107.75  54.00  91.00  156
  4  \w    150.00 175.00   0.50    0.07    --  107.75  19.00  30.00   50
  5  \w    102.00 127.00   0.50    0.07    --  107.75  19.00  30.00   50
  6  \w     98.00 170.00   0.50    0.07    --  107.75  37.00-150.00  144
  7  \w     51.00  92.00   0.50    0.07    --  107.75 -77.00 -30.00   82
  8  \w     37.00  63.00   0.50    0.07    --  107.75 -57.00 -60.00   52
  9  \w     35.00  60.00   0.50    0.07    --  107.75 -57.00-120.00   50
 10  \w    -24.00  49.00   0.50    0.05    --   47.57 -54.00 -52.00  146
 11  \w     35.00  60.00   0.50    0.07    --  107.75 -57.00 150.00   50
 12  \w     35.00  60.00   0.50    0.07    --  107.75 -57.00  90.00   50
 13  \w     37.00  86.00   0.50    0.07    --  107.75 -77.00-120.00   98
 14  \w    -25.00  23.00   0.50    0.05    --   47.57 -19.00-120.00   96
 15  \w    -94.00 -24.00   0.50    0.05    --  -47.57 125.00-150.00  140
 16  \w   -126.00 -88.00   0.50    0.07    -- -100.00 -19.00   0.00   76
 17  \w   -137.00-111.00   0.50    0.07    -- -100.00 -54.00 -52.00   52
 18  \w   -175.00-147.00   0.50    0.07    -- -100.00 -19.00   0.00   56
 19  \w   -166.00-124.00   0.50    0.07    -- -100.00 -57.00  30.00   84
 20  \w   -110.00 -85.00   0.50    0.07    -- -100.00 -57.00  30.00   50
 21  \w    -82.00 -56.00   0.50    0.05    --  -47.57 -54.00 -52.00   52
 22  \w    -65.00 -27.00   0.50    0.07    -- -100.00  54.00  91.00   76
 23  \w    -69.00 -28.00   0.50    0.07    -- -100.00  57.00 120.00   82
 24  \w   -109.00 -73.00   0.50    0.07    -- -100.00  77.00 -90.00   72
 25  \w    -68.00 -30.00   0.50    0.07    -- -100.00  77.00 -90.00   76
 26  \w    -65.00 -40.00   0.50    0.07    -- -100.00  57.00-120.00   50
 27  \w    -68.00 -31.00   0.50    0.07    -- -100.00  57.00 -90.00   74
 28  \w    -68.00 -33.00   0.50    0.07    -- -100.00  57.00 -60.00   70
 29  \w    -62.00  24.00   0.50    0.05    --  -47.57  54.00  91.00  172
;
_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      0.0764030000
_diffrn_orient_matrix_UB_12      -0.0554612000
_diffrn_orient_matrix_UB_13      -0.0026149000
_diffrn_orient_matrix_UB_21      -0.0504495000
_diffrn_orient_matrix_UB_22      -0.0198085000
_diffrn_orient_matrix_UB_23      -0.1377403000
_diffrn_orient_matrix_UB_31      0.0468505000
_diffrn_orient_matrix_UB_32      0.0689982000
_diffrn_orient_matrix_UB_33      -0.0418017000
_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  0.0235
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22319
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.506
_diffrn_reflns_theta_min         2.950
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39697
_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    1.179
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0079(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0926P)^2^+0.2399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1639
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4782
_reflns_number_total             5795
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra04102f2.cif
_cod_data_source_block           8-I
_cod_database_code               7247087
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.918
_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), C3(H3), C5(H5), C6(H6), C10(H10), C12(H12), N2(H2A),
 C19(H19), C20(H20), C22(H22), C23(H23), C26(H26), C28(H28)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3A)
;
_shelx_res_checksum              22097
_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 2.057
_oxdiff_exptl_absorpt_empirical_full_min 0.585