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_7247082
_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         'C15 H15 N O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28
_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             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                 112.042(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6295(14)
_cell_length_b                   6.0707(6)
_cell_length_c                   15.0512(17)
_cell_measurement_reflns_used    2684
_cell_measurement_temperature    303.88(10)
_cell_measurement_theta_max      73.0040
_cell_measurement_theta_min      3.5900
_cell_volume                     1239.0(2)
_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      303.88(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.928
_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     40.00  65.50   1.50    0.50    --   46.57  37.00  60.00   17
  2  \w     88.00 119.50   1.50    0.50    --   46.57  37.00  60.00   21
  3  \w    118.00 172.00   1.50    2.00    --  104.25  89.00 -19.00   36
  4  \w     38.00  86.00   1.50    2.00    --  104.25 -94.00  60.00   32
  5  \w     36.00  61.50   1.50    2.00    --  104.25 -61.00   0.00   17
  6  \w     60.00  99.00   1.50    2.00    --  104.25 -89.00-135.00   26
  7  \w     36.00  64.50   1.50    2.00    --  104.25 -61.00-150.00   19
  8  \w      7.00  43.00   1.50    0.50    --   46.57 -89.00-135.00   24
  9  \w   -111.00 -84.00   1.50    0.50    --  -46.57-125.00  90.00   18
 10  \w   -115.00 -79.00   1.50    0.50    --  -46.57-125.00   0.00   24
 11  \w   -175.00-115.00   1.50    2.00    -- -102.00 -89.00-135.00   40
 12  \w   -115.00 -88.00   1.50    2.00    -- -102.00 -61.00 -90.00   18
 13  \w   -175.00-118.00   1.50    2.00    -- -102.00 -61.00 -90.00   38
 14  \w   -175.00-140.50   1.50    2.00    -- -102.00 -30.00-120.00   23
 15  \w   -119.00 -89.00   1.50    2.00    -- -102.00 -30.00-120.00   20
 16  \w    -74.00  26.50   1.50    0.50    --  -46.57  89.00 -19.00   67
 17  \w    -98.00 -59.00   1.50    2.00    -- -102.00  89.00 -19.00   26
 18  \w    -68.00 -35.00   1.50    2.00    -- -102.00  61.00 -30.00   22
 19  \w    -60.00 -30.00   1.50    2.00    -- -102.00  61.00 -60.00   20
 20  \w    -68.00 -42.50   1.50    2.00    -- -102.00  61.00-180.00   17
 21  \w    -69.00 -42.00   1.50    2.00    -- -102.00  61.00   0.00   18
 22  \w    -60.00 -30.00   1.50    2.00    -- -102.00  61.00 120.00   20
 23  \w    -58.00 -31.00   1.50    2.00    -- -102.00  61.00 150.00   18
 24  \w    -25.00  29.00   1.50    0.50    --  -46.57  19.00  90.00   36
;
_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      -0.0195492000
_diffrn_orient_matrix_UB_12      -0.0391014000
_diffrn_orient_matrix_UB_13      -0.1067858000
_diffrn_orient_matrix_UB_21      -0.0535357000
_diffrn_orient_matrix_UB_22      0.2231066000
_diffrn_orient_matrix_UB_23      -0.0251954000
_diffrn_orient_matrix_UB_31      0.0982542000
_diffrn_orient_matrix_UB_32      0.1142420000
_diffrn_orient_matrix_UB_33      0.0129406000
_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  0.0425
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7285
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.003
_diffrn_reflns_theta_min         3.593
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22335
_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    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0030(7)
_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   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2409
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0818P)^2^+0.1033P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1638
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1766
_reflns_number_total             2409
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra04102f2.cif
_cod_data_source_block           6-II
_cod_database_code               7247082
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.886
_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
2. Restrained distances
 O1-H1
 0.86 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C12(H12), C13(H13)
3.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              98622
_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 3.453
_oxdiff_exptl_absorpt_empirical_full_min 0.353