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_7244039
_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         '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 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-25
_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                90
_cell_angle_beta                 108.3051(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.66720(18)
_cell_length_b                   7.41660(10)
_cell_length_c                   15.6676(3)
_cell_measurement_reflns_used    6015
_cell_measurement_temperature    300.43(10)
_cell_measurement_theta_max      77.2920
_cell_measurement_theta_min      2.9530
_cell_volume                     1287.13(4)
_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      300.43(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.930
_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     46.00 120.00   0.50    0.05    --   47.57  72.00-156.00  148
  2  \w     88.00 167.00   0.50    0.05    --  107.75  72.00-156.00  158
  3  \w    130.00 174.00   0.50    0.05    --  107.75  37.00  90.00   88
  4  \w     97.00 168.00   0.50    0.05    --  107.75  57.00 150.00  142
  5  \w      8.00  34.00   0.50    0.05    --   47.57 -72.00  72.00   52
  6  \w    -65.00 -39.00   0.50    0.05    --  -47.57  72.00-156.00   52
  7  \w    -36.00  23.00   0.50    0.05    --  -47.57  72.00-156.00  118
  8  \w    -24.00  23.00   0.50    0.05    --   47.57 -19.00 -90.00   94
  9  \w     62.00 104.00   0.50    0.05    --  107.75 -99.00 -90.00   84
 10  \w    -24.00  11.00   0.50    0.05    --   47.57 -19.00  60.00   70
 11  \w     35.00  83.00   0.50    0.05    --  107.75 -72.00  72.00   96
 12  \w     35.00  60.00   0.50    0.05    --  107.75 -57.00  90.00   50
 13  \w     36.00  62.00   0.50    0.05    --  107.75 -57.00   0.00   52
 14  \w     35.00  61.00   0.50    0.05    --  107.75 -57.00-120.00   52
 15  \w    -93.00 -27.00   0.50    0.05    -- -100.00  72.00-156.00  132
 16  \w    -66.00 -28.00   0.50    0.05    -- -100.00  57.00 -30.00   76
 17  \w    -69.00 -30.00   0.50    0.05    -- -100.00  57.00  30.00   78
 18  \w    -65.00 -39.00   0.50    0.05    -- -100.00  57.00  60.00   52
 19  \w    -60.00 -34.00   0.50    0.05    -- -100.00  57.00 150.00   52
 20  \w   -129.00 -93.00   0.50    0.05    -- -100.00 -19.00 120.00   72
 21  \w   -173.00-144.00   0.50    0.05    -- -100.00 -19.00 120.00   58
 22  \w   -157.00-130.00   0.50    0.05    -- -100.00 -72.00  72.00   54
 23  \w    -73.00 -27.00   0.50    0.05    --  -47.57 -72.00  72.00   92
;
_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      -0.1070291000
_diffrn_orient_matrix_UB_12      -0.1201963000
_diffrn_orient_matrix_UB_13      -0.0513382000
_diffrn_orient_matrix_UB_21      -0.0182444000
_diffrn_orient_matrix_UB_22      0.1152811000
_diffrn_orient_matrix_UB_23      -0.0850320000
_diffrn_orient_matrix_UB_31      0.0870113000
_diffrn_orient_matrix_UB_32      -0.1241543000
_diffrn_orient_matrix_UB_33      -0.0290915000
_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  0.0139
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8348
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.457
_diffrn_reflns_theta_min         3.991
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73751
_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    1.245
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.019(2)
_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   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2546
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0656P)^2^+0.2139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1255
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2267
_reflns_number_total             2546
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01407b2.cif
_cod_data_source_block           HDMPA-II
_cod_depositor_comments
'Adding full bibliography for 7244038--7244041.cif.'
_cod_database_code               7244039
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.961
_reflns_odcompleteness_completeness 99.12
_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, 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 Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              67667
_shelx_hkl_checksum              39388
_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 1.509
_oxdiff_exptl_absorpt_empirical_full_min 0.691