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_7244041
_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, C13 H8 Cl2 N O2, C2 H8 N'
_chemical_formula_sum            'C28 H25 Cl4 N3 O4'
_chemical_formula_weight         609.31
_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             2021-05-30
_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                 99.2820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2255(2)
_cell_length_b                   24.6280(3)
_cell_length_c                   8.16320(10)
_cell_measurement_reflns_used    12006
_cell_measurement_temperature    259.6(6)
_cell_measurement_theta_max      77.0970
_cell_measurement_theta_min      3.5910
_cell_volume                     2822.49(6)
_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      N~2~
_diffrn_ambient_temperature      259.6(6)
_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 0.948
_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    113.00 157.00   0.50    0.20    --  107.75 112.00-122.00   88
  2  \w    133.00 174.00   0.50    0.20    --  107.75  37.00-150.00   82
  3  \w     98.00 124.00   0.50    0.20    --  107.75  37.00-150.00   52
  4  \w    -27.00  -2.00   0.50    0.07    --   47.57 -19.00-180.00   50
  5  \w     -7.00  18.00   0.50    0.07    --   47.57 -19.00-150.00   50
  6  \w    -25.00  31.00   0.50    0.07    --   47.57 -37.00  30.00  112
  7  \w    -23.00  23.00   0.50    0.07    --   47.57 -19.00 150.00   92
  8  \w      9.00  61.00   0.50    0.07    --   47.57-112.00 145.00  104
  9  \w     66.00  92.00   0.50    0.20    --  107.75-112.00 145.00   52
 10  \w     86.00 112.00   0.50    0.20    --  107.75-125.00  60.00   52
 11  \w     36.00  61.00   0.50    0.20    --  107.75-125.00  60.00   50
 12  \w     41.00 111.00   0.50    0.20    --  107.75-125.00-180.00  140
 13  \w     35.00  60.00   0.50    0.20    --  107.75 -57.00  30.00   50
 14  \w     36.00  61.00   0.50    0.20    --  107.75 -57.00-180.00   50
 15  \w     35.00  99.00   0.50    0.20    --  107.75 -77.00 150.00  128
 16  \w    -56.00 -30.00   0.50    0.07    --  -47.57 112.00-122.00   52
 17  \w   -108.00 -43.00   0.50    0.20    -- -100.00 125.00 -90.00  130
 18  \w   -107.00 -76.00   0.50    0.20    -- -100.00 112.00-122.00   62
 19  \w    -69.00 -31.00   0.50    0.20    -- -100.00  57.00 -90.00   76
 20  \w    -61.00 -35.00   0.50    0.20    -- -100.00  57.00  30.00   52
 21  \w    -56.00 -27.00   0.50    0.20    -- -100.00  57.00  90.00   58
 22  \w   -175.00-138.00   0.50    0.20    -- -100.00 -19.00 150.00   74
 23  \w   -130.00 -90.00   0.50    0.20    -- -100.00 -19.00 150.00   80
 24  \w   -167.00 -90.00   0.50    0.20    -- -100.00-112.00 145.00  154
 25  \w   -127.00 -91.00   0.50    0.20    -- -100.00 -99.00  30.00   72
 26  \w   -116.00 -34.00   0.50    0.07    --  -47.57 -57.00-120.00  164
;
_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      -0.0125524000
_diffrn_orient_matrix_UB_12      0.0602636000
_diffrn_orient_matrix_UB_13      0.0423001000
_diffrn_orient_matrix_UB_21      0.1015397000
_diffrn_orient_matrix_UB_22      0.0120109000
_diffrn_orient_matrix_UB_23      -0.0332572000
_diffrn_orient_matrix_UB_31      -0.0396905000
_diffrn_orient_matrix_UB_32      0.0117122000
_diffrn_orient_matrix_UB_33      -0.1834592000
_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  0.0251
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20242
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.553
_diffrn_reflns_theta_min         3.148
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.142
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70681
_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    1.434
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.722
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5693
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0597P)^2^+1.7018P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4939
_reflns_number_total             5693
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01407b2.cif
_cod_data_source_block           S
_cod_depositor_comments
'Adding full bibliography for 7244038--7244041.cif.'
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               7244041
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.886
_shelx_estimated_absorpt_t_min   0.820
_reflns_odcompleteness_completeness 99.92
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 N3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), N2(H2),
  C16(H16), C17(H17), C18(H18), C19(H19), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              91700
_shelx_hkl_checksum              8157
_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 1.713
_oxdiff_exptl_absorpt_empirical_full_min 0.667