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_7247086
_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      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             2021-10-06
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                88.249(2)
_cell_angle_beta                 83.997(2)
_cell_angle_gamma                79.406(3)
_cell_formula_units_Z            4
_cell_length_a                   6.2842(2)
_cell_length_b                   13.1283(4)
_cell_length_c                   15.8787(3)
_cell_measurement_reflns_used    9669
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.0210
_cell_measurement_theta_min      3.4080
_cell_volume                     1280.53(6)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_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 0.942
_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     33.00 108.00   0.50    0.05    --   47.57  77.00 -30.00  150
  2  \w     87.00 160.00   0.50    0.07    --  107.75 110.00 -46.00  146
  3  \w    -26.00  10.00   0.50    0.05    --   47.57 -19.00-120.00   72
  4  \w    -22.00  14.00   0.50    0.05    --   47.57 -19.00-150.00   72
  5  \w     75.00 100.00   0.50    0.07    --  107.75 -99.00-120.00   50
  6  \w     71.00  99.00   0.50    0.07    --  107.75-110.00-141.00   56
  7  \w     36.00 109.00   0.50    0.07    --  107.75-125.00-150.00  146
  8  \w     17.00  58.00   0.50    0.05    --   47.57-110.00-141.00   82
  9  \w     47.00 104.00   0.50    0.07    --  107.75 -99.00 120.00  114
 10  \w     37.00  89.00   0.50    0.07    --  107.75 -99.00  90.00  104
 11  \w     38.00  63.00   0.50    0.07    --  107.75 -57.00   0.00   50
 12  \w     35.00  60.00   0.50    0.07    --  107.75 -57.00 120.00   50
 13  \w     76.00 101.00   0.50    0.07    --  107.75 -77.00 -30.00   50
 14  \w     37.00  96.00   0.50    0.07    --  107.75 -77.00 -90.00  118
 15  \w     50.00 101.00   0.50    0.07    --  107.75 -77.00-150.00  102
 16  \w     37.00  62.00   0.50    0.07    --  107.75 -57.00-180.00   50
 17  \w    -56.00  25.00   0.50    0.05    --  -47.57  57.00 -90.00  162
 18  \w    -69.00 -44.00   0.50    0.07    -- -100.00  57.00-180.00   50
 19  \w    -31.00  16.00   0.50    0.05    --  -47.57  37.00-150.00   94
 20  \w    -64.00 -27.00   0.50    0.07    -- -100.00 125.00   0.00   74
 21  \w    -66.00 -28.00   0.50    0.07    -- -100.00 125.00 -30.00   76
 22  \w   -106.00 -80.00   0.50    0.07    -- -100.00 110.00 -46.00   52
 23  \w   -112.00 -74.00   0.50    0.07    -- -100.00 125.00   0.00   76
 24  \w   -112.00 -71.00   0.50    0.07    -- -100.00 125.00 -30.00   82
 25  \w    -75.00 -27.00   0.50    0.07    -- -100.00 109.00-142.95   96
 26  \w   -108.00 -83.00   0.50    0.07    -- -100.00 109.00-142.95   50
 27  \w    -93.00 -59.00   0.50    0.05    --  -47.57 125.00-180.00   68
 28  \w    -56.00 -23.00   0.50    0.05    --  -47.57 125.00-180.00   66
 29  \w    -82.00 -15.00   0.50    0.05    --  -47.57 110.00 -46.00  134
 30  \w   -128.00 -87.00   0.50    0.07    -- -100.00 -37.00  90.00   82
 31  \w   -167.00-140.00   0.50    0.07    -- -100.00 -37.00  90.00   54
 32  \w   -172.00 -85.00   0.50    0.07    -- -100.00 -57.00   0.00  174
 33  \w   -159.00 -85.00   0.50    0.07    -- -100.00 -57.00 -30.00  148
 34  \w   -171.00 -87.00   0.50    0.07    -- -100.00 -57.00 -60.00  168
 35  \w   -117.00 -92.00   0.50    0.07    -- -100.00 -37.00-120.00   50
 36  \w   -162.00-129.00   0.50    0.07    -- -100.00 -37.00-120.00   66
 37  \w   -131.00-105.00   0.50    0.07    -- -100.00-110.00-141.00   52
 38  \w   -127.00 -92.00   0.50    0.07    -- -100.00-125.00 -60.00   70
 39  \w   -173.00-140.00   0.50    0.07    -- -100.00-125.00 -60.00   66
;
_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      0.2402471000
_diffrn_orient_matrix_UB_12      0.0060815000
_diffrn_orient_matrix_UB_13      0.0064441000
_diffrn_orient_matrix_UB_21      -0.0521720000
_diffrn_orient_matrix_UB_22      0.0223240000
_diffrn_orient_matrix_UB_23      0.0953436000
_diffrn_orient_matrix_UB_31      0.0489655000
_diffrn_orient_matrix_UB_32      -0.1171257000
_diffrn_orient_matrix_UB_33      0.0196600000
_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  0.0361
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15039
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.590
_diffrn_reflns_theta_min         2.798
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50591
_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 dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0048(11)
_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   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5118
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0575
_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^)+(0.0920P)^2^+0.1769P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1705
_refine_ls_wR_factor_ref         0.1782
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4064
_reflns_number_total             5118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra04102f2.cif
_cod_data_source_block           5
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C30 H30 N2 O4'
_cod_original_formula_weight         482.56
_cod_original_formula_moiety         '2(C15 H15 N O2)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1280.52(6)
_cod_database_code               7247086
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
 H3-O3
 0.82 with sigma of 0.01
 O1-H1
 0.82 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14),
 N2(H2), C19(H19), C20(H20), C21(H21), C25(H25), C26(H26), C28(H28), C29(H29)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              2498
_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 2.632
_oxdiff_exptl_absorpt_empirical_full_min 0.561