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_7244638
_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         'C16 H17 N O2'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.30
_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                 91.589(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0796(3)
_cell_length_b                   10.1603(10)
_cell_length_c                   26.6290(19)
_cell_measurement_reflns_used    3376
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.1740
_cell_measurement_theta_min      3.3360
_cell_volume                     1373.80(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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 0.984
_diffrn_measured_fraction_theta_max 0.919
_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    -28.00  27.00   1.00    0.22    --  -47.57  19.00  60.00   55
  2  \w     71.00 114.00   1.00    0.22    --   47.57 139.00-115.00   43
  3  \w     96.00 128.00   1.00    0.89    --  107.75  37.00  60.00   32
  4  \w     36.00  63.00   1.00    0.89    --  107.75 -57.00  60.00   27
  5  \w     51.00  76.00   1.00    0.89    --  107.75-130.00  -2.00   25
  6  \w     45.00  91.00   1.00    0.89    --  107.75-125.00  30.00   46
  7  \w     58.00  85.00   1.00    0.22    --   47.57-139.00-176.00   27
  8  \w     68.00  93.00   1.00    0.89    --  107.75-139.00-176.00   25
  9  \w    -24.00  23.00   1.00    0.22    --   47.57 -19.00-120.00   47
 10  \w    -86.00 -61.00   1.00    0.22    --  -47.57 130.00  69.00   25
 11  \w    -26.00  15.00   1.00    0.22    --   47.57 -19.00 150.00   41
 12  \w    -85.00 -59.00   1.00    0.22    --  -47.57 139.00-115.00   26
 13  \w    -76.00 -51.00   1.00    0.89    -- -100.00 139.00-115.00   25
 14  \w   -120.00 -86.00   1.00    0.89    -- -100.00 136.00-104.61   34
 15  \w    -60.00 -27.00   1.00    0.89    -- -100.00  57.00 -60.00   33
 16  \w    -69.00 -37.00   1.00    0.89    -- -100.00  57.00 -90.00   32
 17  \w    -73.00 -31.00   1.00    0.89    -- -100.00 141.00  49.35   42
 18  \w   -112.00 -48.00   1.00    0.89    -- -100.00 125.00  30.00   64
 19  \w   -112.00 -62.00   1.00    0.89    -- -100.00 125.00   0.00   50
 20  \w   -123.00 -91.00   1.00    0.89    -- -100.00 141.00  49.35   32
 21  \w   -175.00-100.00   1.00    0.89    -- -100.00 -19.00   0.00   75
 22  \w   -150.00-125.00   1.00    0.89    -- -100.00-130.00  -2.00   25
 23  \w   -137.00 -89.00   1.00    0.89    -- -100.00-125.00  60.00   48
 24  \w   -118.00 -74.00   1.00    0.22    --  -47.57-139.00-176.00   44
 25  \w   -146.00 -76.00   1.00    0.89    -- -100.00-139.00-176.00   70
;
_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      -0.0117664000
_diffrn_orient_matrix_UB_12      -0.1247204000
_diffrn_orient_matrix_UB_13      -0.0328835000
_diffrn_orient_matrix_UB_21      0.0006946000
_diffrn_orient_matrix_UB_22      -0.0860876000
_diffrn_orient_matrix_UB_23      0.0476653000
_diffrn_orient_matrix_UB_31      -0.3030209000
_diffrn_orient_matrix_UB_32      0.0046518000
_diffrn_orient_matrix_UB_33      -0.0002583000
_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  0.0622
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8751
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.676
_diffrn_reflns_theta_min         3.321
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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    1.234
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0717
_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^)+(0.0892P)^2^+0.4680P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1822
_refine_ls_wR_factor_ref         0.2009
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1883
_reflns_number_total             2699
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00126h2.cif
_cod_data_source_block           5-I
_cod_original_cell_volume        1373.79(19)
_cod_database_code               7244638
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.932
_reflns_odcompleteness_completeness 98.84
_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 Riding coordinates:
 N1(H1A)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              98483
_shelx_hkl_checksum              27871
_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 6.994
_oxdiff_exptl_absorpt_empirical_full_min 0.538