Polymorphism and cocrystal salt formation of 2-((2,6-dichlorophenyl)amino)benzoic acid, harvest of a second form of 2-((2,6-dimethylphenyl)amino)benzoic acid, and isomorphism between the two systems
Zhoujin, Yunping; Li, Yuping; Zhang, Mingtao; Parkin, Sean; Guo, Ju; Li, Tonglei; Yu, Faquan; Long, Sihui; CrystEngComm 24 (2022) 681–690; doi:10.1039/D1CE01407B

data_7244038
_publ_section_title
;
 Polymorphism and cocrystal salt formation of
 2-((2,6-dichlorophenyl)amino)benzoic acid, harvest of a second form of
 2-((2,6-dimethylphenyl)amino)benzoic acid, and isomorphism between the
 two systems
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              681
_journal_page_last               690
_journal_paper_doi               10.1039/D1CE01407B
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C13 H9 Cl2 N O2'
_chemical_formula_sum            'C13 H9 Cl2 N O2'
_chemical_formula_weight         282.11
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-03
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-10-13 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                72.216(2)
_cell_angle_beta                 84.210(2)
_cell_angle_gamma                74.767(2)
_cell_formula_units_Z            2
_cell_length_a                   7.38490(10)
_cell_length_b                   8.0981(2)
_cell_length_c                   11.1254(2)
_cell_measurement_reflns_used    5708
_cell_measurement_temperature    299.78(10)
_cell_measurement_theta_max      77.0950
_cell_measurement_theta_min      6.1850
_cell_volume                     611.13(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (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_environment      air
_diffrn_ambient_temperature      299.78(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.975
_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    124.00 150.00   0.50    0.05    --  107.75  91.00  81.00   52
  2  \w     79.00 120.00   0.50    0.05    --  107.75  91.00  81.00   82
  3  \w     99.00 125.00   0.50    0.05    --  107.75  37.00 150.00   52
  4  \w    144.00 169.00   0.50    0.05    --  107.75  37.00 150.00   50
  5  \w     95.00 171.00   0.50    0.05    --  107.75  37.00  30.00  152
  6  \w    -25.00  26.00   0.50    0.05    --   47.57 -37.00  60.00  102
  7  \w    -24.00  22.00   0.50    0.05    --   47.57 -19.00-180.00   92
  8  \w    -24.00   2.00   0.50    0.05    --   47.57 -19.00-120.00   52
  9  \w    -27.00  -1.00   0.50    0.05    --   47.57 -19.00 -90.00   52
 10  \w    -27.00  23.00   0.50    0.05    --   47.57 -19.00 -30.00  100
 11  \w     36.00  61.00   0.50    0.05    --  107.75 -91.00 -31.00   50
 12  \w     79.00 104.00   0.50    0.05    --  107.75 -99.00 -60.00   50
 13  \w     35.00  91.00   0.50    0.05    --  107.75-125.00 -60.00  112
 14  \w     45.00 112.00   0.50    0.05    --  107.75-125.00-120.00  134
 15  \w     48.00 108.00   0.50    0.05    --  107.75-125.00-150.00  120
 16  \w     52.00 104.00   0.50    0.05    --  107.75 -99.00 -90.00  104
 17  \w     62.00  88.00   0.50    0.05    --  107.75 -91.00 -31.00   52
 18  \w     41.00 103.00   0.50    0.05    --  107.75 -99.00  60.00  124
 19  \w     35.00 104.00   0.50    0.05    --  107.75 -99.00 120.00  138
 20  \w     35.00  60.00   0.50    0.05    --  107.75 -57.00 120.00   50
 21  \w     42.00  70.00   0.50    0.05    --   47.57 -91.00 -31.00   56
 22  \w    -21.00  34.00   0.50    0.05    --   47.57 -91.00 -31.00  110
 23  \w     40.00 103.00   0.50    0.05    --  107.75 -77.00 -30.00  126
 24  \w    -66.00 -34.00   0.50    0.05    -- -100.00  91.00  81.00   64
 25  \w    -24.00  22.00   0.50    0.05    --  -47.57  91.00  81.00   92
 26  \w   -112.00 -57.00   0.50    0.05    -- -100.00 125.00  30.00  110
 27  \w    -94.00 -35.00   0.50    0.05    --  -47.57 125.00-180.00  118
 28  \w    -69.00 -27.00   0.50    0.05    -- -100.00  57.00-180.00   84
 29  \w    -69.00 -31.00   0.50    0.05    -- -100.00  57.00 -90.00   76
 30  \w    -68.00 -29.00   0.50    0.05    -- -100.00  57.00 -60.00   78
 31  \w   -123.00 -87.00   0.50    0.05    -- -100.00 -37.00-180.00   72
 32  \w   -172.00-129.00   0.50    0.05    -- -100.00 -37.00-180.00   86
 33  \w   -172.00 -94.00   0.50    0.05    -- -100.00 -37.00 -60.00  156
 34  \w   -129.00 -90.00   0.50    0.05    -- -100.00 -19.00  30.00   78
 35  \w   -175.00-140.00   0.50    0.05    -- -100.00 -19.00  30.00   70
 36  \w   -118.00 -92.00   0.50    0.05    -- -100.00 -91.00 -31.00   52
;
_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      0.0420121000
_diffrn_orient_matrix_UB_12      -0.0566093000
_diffrn_orient_matrix_UB_13      -0.1221314000
_diffrn_orient_matrix_UB_21      0.0961790000
_diffrn_orient_matrix_UB_22      0.1546865000
_diffrn_orient_matrix_UB_23      -0.0584672000
_diffrn_orient_matrix_UB_31      0.1890864000
_diffrn_orient_matrix_UB_32      -0.1237981000
_diffrn_orient_matrix_UB_33      0.0531367000
_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  0.0215
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6338
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.266
_diffrn_reflns_theta_min         4.174
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (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    1.533
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.035(5)
_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   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0685P)^2^+0.1666P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1132
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2309
_reflns_number_total             2412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01407b2.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 7244038--7244041.cif.'
_cod_database_code               7244038
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.765
_reflns_odcompleteness_completeness 97.47
_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 O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              2812
_shelx_hkl_checksum              91215
_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 2.336
_oxdiff_exptl_absorpt_empirical_full_min 0.576