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_7244040
_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      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   geom
_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
;
2021-10-13 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.487(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4611(3)
_cell_length_b                   6.86735(12)
_cell_length_c                   15.5404(3)
_cell_measurement_reflns_used    5906
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.7520
_cell_measurement_theta_min      3.9410
_cell_volume                     1245.75(5)
_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 0.996
_diffrn_measured_fraction_theta_max 0.941
_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    -25.00  23.00   0.50    0.05    --   47.57 -19.00  30.00   96
  2  \w    -20.00   5.00   0.50    0.05    --   47.57 -19.00 -60.00   50
  3  \w    -25.00  36.00   0.50    0.05    --   47.57 -37.00 -90.00  122
  4  \w     92.00 166.00   0.50    0.07    --  107.75  97.00 134.00  148
  5  \w    -76.00 -40.00   0.50    0.05    --  -47.57  97.00 134.00   72
  6  \w    -36.00   8.00   0.50    0.05    --  -47.57  97.00 134.00   88
  7  \w    -80.00 -47.00   0.50    0.07    -- -100.00  97.00 134.00   66
  8  \w    -69.00 -39.00   0.50    0.07    -- -100.00  57.00   0.00   60
  9  \w   -108.00 -82.00   0.50    0.07    -- -100.00  77.00 -30.00   52
 10  \w    -62.00 -32.00   0.50    0.07    -- -100.00  57.00-120.00   60
 11  \w    -67.00 -28.00   0.50    0.07    -- -100.00  57.00 -30.00   78
 12  \w    -58.00 -27.00   0.50    0.07    -- -100.00  57.00 -90.00   62
 13  \w    -69.00 -29.00   0.50    0.07    -- -100.00  57.00 120.00   80
 14  \w     57.00 106.00   0.50    0.07    --  107.75 -97.00  26.00   98
 15  \w    -18.00  32.00   0.50    0.05    --   47.57 -97.00  26.00  100
 16  \w   -173.00-119.00   0.50    0.07    -- -100.00 -77.00  60.00  108
 17  \w   -115.00 -78.00   0.50    0.07    -- -100.00 -77.00  60.00   74
 18  \w   -123.00 -89.00   0.50    0.07    -- -100.00-125.00 -30.00   68
 19  \w   -171.00-131.00   0.50    0.07    -- -100.00-125.00 -30.00   80
 20  \w   -157.00-131.00   0.50    0.07    -- -100.00 -97.00  26.00   52
 21  \w     35.00  62.00   0.50    0.07    --  107.75 -57.00  90.00   54
 22  \w     35.00  61.00   0.50    0.07    --  107.75 -57.00 120.00   52
 23  \w     70.00 101.00   0.50    0.07    --  107.75 -77.00  60.00   62
 24  \w     35.00  60.00   0.50    0.07    --  107.75 -57.00  30.00   50
 25  \w     35.00  61.00   0.50    0.07    --  107.75 -57.00-150.00   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      0.1210816000
_diffrn_orient_matrix_UB_12      -0.0361399000
_diffrn_orient_matrix_UB_13      0.0700709000
_diffrn_orient_matrix_UB_21      -0.0011049000
_diffrn_orient_matrix_UB_22      -0.2067571000
_diffrn_orient_matrix_UB_23      -0.0387420000
_diffrn_orient_matrix_UB_31      0.0525503000
_diffrn_orient_matrix_UB_32      0.0791724000
_diffrn_orient_matrix_UB_33      -0.0691872000
_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  0.0434
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7970
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.033
_diffrn_reflns_theta_min         3.939
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53625
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0023(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   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0651P)^2^+0.1556P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1167
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2200
_reflns_number_total             2483
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01407b2.cif
_cod_data_source_block           II
_cod_depositor_comments
'Adding full bibliography for 7244038--7244041.cif.'
_cod_original_cell_volume        1245.74(4)
_cod_database_code               7244040
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.836
_shelx_estimated_absorpt_t_min   0.630
_reflns_odcompleteness_completeness 99.67
_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(H1A), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              51202
_shelx_hkl_checksum              22389
_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 4.165
_oxdiff_exptl_absorpt_empirical_full_min 0.361