Conformational Flexibility and Substitution Pattern Lead to Polymorphism of 3-Methyl-2-(phenylamino)benzoic acid
Tao, Yang; Liu, Xiaoting; Zhoujin, Yunping; Zhou, Panpan; Parkin, Sean R.; Li, Tonglei; Guo, Ju; Yu, Faquan; Long, Sihui; CrystEngComm  (2022) –; doi:10.1039/D2CE00126H

data_7244637
_publ_section_title
;
 Conformational Flexibility and Substitution Pattern Lead to Polymorphism
 of 3-Methyl-2-(phenylamino)benzoic acid
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00126H
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-12-14
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-10-28 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.715(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0335(12)
_cell_length_b                   6.9116(5)
_cell_length_c                   13.0522(10)
_cell_measurement_reflns_used    4034
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.4910
_cell_measurement_theta_min      6.1760
_cell_volume                     1268.52(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'ShelXS (Sheldrick, 2008)'
_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 0.987
_diffrn_measured_fraction_theta_max 0.926
_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     36.00 117.00   0.50    0.05    --   47.45  37.00   0.00  162
  2  \w     72.00  97.00   0.50    0.05    --   47.45 131.00-103.00   50
  3  \w     73.00  99.00   0.50    0.19    --  107.75 131.00-103.00   52
  4  \w     70.00 117.00   0.50    0.05    --   47.45 138.00  72.00   94
  5  \w    -16.00  10.00   0.50    0.05    --   47.45 -19.00-150.00   52
  6  \w    -26.00  23.00   0.50    0.05    --   47.45 -19.00-180.00   98
  7  \w     63.00 106.00   0.50    0.19    --  107.75 -99.00-180.00   86
  8  \w     62.00 100.00   0.50    0.19    --  107.75 -77.00-180.00   76
  9  \w     51.00  76.00   0.50    0.19    --  107.75-131.00-174.00   50
 10  \w     36.00  62.00   0.50    0.19    --  107.75 -57.00-180.00   52
 11  \w     78.00 116.00   0.50    0.19    --  107.75-138.00  10.00   76
 12  \w     80.00 105.00   0.50    0.19    --  107.75 -99.00  30.00   50
 13  \w     35.00  61.00   0.50    0.19    --  107.75 -57.00  30.00   52
 14  \w     38.00  74.00   0.50    0.19    --  107.75 -99.00  30.00   72
 15  \w    -19.00  20.00   0.50    0.05    --   47.45 -19.00  60.00   78
 16  \w    -81.00 -55.00   0.50    0.05    --  -47.45 131.00-103.00   52
 17  \w    -73.00 -27.00   0.50    0.19    -- -100.00 131.00-103.00   92
 18  \w   -108.00 -58.00   0.50    0.19    -- -100.00 110.00 -87.06  100
 19  \w    -86.00 -33.00   0.50    0.05    --  -47.45 138.00  72.00  106
 20  \w    -53.00 -27.00   0.50    0.19    -- -100.00  57.00  60.00   52
 21  \w    -56.00 -27.00   0.50    0.19    -- -100.00  57.00 120.00   58
 22  \w   -120.00 -32.00   0.50    0.19    -- -100.00 138.00  72.00  176
 23  \w   -136.00-100.00   0.50    0.19    -- -100.00 -19.00   0.00   72
 24  \w   -121.00 -88.00   0.50    0.19    -- -100.00 -57.00  90.00   66
 25  \w   -158.00 -86.00   0.50    0.19    -- -100.00-125.00 150.00  144
 26  \w   -172.00-141.00   0.50    0.19    -- -100.00 -19.00   0.00   62
 27  \w   -170.00-127.00   0.50    0.19    -- -100.00 -57.00  90.00   86
;
_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      0.0519504000
_diffrn_orient_matrix_UB_12      -0.1693309000
_diffrn_orient_matrix_UB_13      0.0738587000
_diffrn_orient_matrix_UB_21      -0.0624366000
_diffrn_orient_matrix_UB_22      -0.1448072000
_diffrn_orient_matrix_UB_23      -0.0846885000
_diffrn_orient_matrix_UB_31      0.0735674000
_diffrn_orient_matrix_UB_32      -0.0036841000
_diffrn_orient_matrix_UB_33      -0.0574587000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0087
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4306
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.245
_diffrn_reflns_theta_min         6.295
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         4306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0734
_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^)+(0.1408P)^2^+0.1163P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2059
_refine_ls_wR_factor_ref         0.2154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3727
_reflns_number_total             4306
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.8883\% 
around [-0.38 0.00 0.93] (reciprocal) or [0.00 -0.00 1.00] (direct)
;
_cod_data_source_file            d2ce00126h2.cif
_cod_data_source_block           3
_cod_database_code               7244637
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.496(3)
 0.504(3)
2. 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
3.a Riding coordinates:
 N3(H3)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C13(H13), C15(H15), C1(H1A), C2(H2)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              6327
_shelx_hkl_checksum              35832
_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 1.829
_oxdiff_exptl_absorpt_empirical_full_min 0.452
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2