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_7244640
_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   geom
_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                 106.196(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2982(2)
_cell_length_b                   15.8116(3)
_cell_length_c                   7.97734(18)
_cell_measurement_reflns_used    6807
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.9240
_cell_measurement_theta_min      2.8220
_cell_volume                     1368.54(5)
_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 0.991
_diffrn_measured_fraction_theta_max 0.939
_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    -44.00  13.00   0.50    0.05    --  -47.57  37.00 -90.00  114
  2  \w    -59.00 -30.00   0.50    0.05    -- -100.00 134.00 -72.00   58
  3  \w    -87.00 -61.00   0.50    0.05    --  -47.57 134.00 -72.00   52
  4  \w   -116.00 -66.00   0.50    0.05    -- -100.00 134.00 -72.00  100
  5  \w   -106.00 -28.00   0.50    0.05    -- -100.00  77.00 -60.00  156
  6  \w    -69.00 -44.00   0.50    0.05    -- -100.00  57.00 -60.00   50
  7  \w   -113.00 -87.00   0.50    0.05    -- -100.00 -19.00 -90.00   52
  8  \w   -172.00-144.00   0.50    0.05    -- -100.00 -57.00-120.00   56
  9  \w   -174.00-120.00   0.50    0.05    -- -100.00 -19.00 -90.00  108
 10  \w    -80.00 -55.00   0.50    0.05    --  -47.57 135.00 107.00   50
 11  \w     78.00 119.00   0.50    0.05    --   47.57 134.00 -72.00   82
 12  \w     89.00 123.00   0.50    0.05    --  107.75 134.00 -72.00   68
 13  \w     96.00 172.00   0.50    0.05    --  107.75  37.00-180.00  152
 14  \w     38.00  63.00   0.50    0.05    --   47.57-135.00  41.00   50
 15  \w     53.00  78.00   0.50    0.05    --  107.75-135.00  41.00   50
 16  \w     61.00 111.00   0.50    0.05    --  107.75-125.00  60.00  100
 17  \w     36.00  62.00   0.50    0.05    --  107.75 -57.00  60.00   52
 18  \w     37.00  62.00   0.50    0.05    --  107.75 -57.00  90.00   50
 19  \w    115.00 141.00   0.50    0.05    --  107.75  19.00 120.00   52
 20  \w     70.00 105.00   0.50    0.05    --   47.57 135.00 107.00   70
 21  \w    -27.00  -1.00   0.50    0.05    --   47.57 -19.00-150.00   52
 22  \w    -21.00   4.00   0.50    0.05    --   47.57 -19.00-180.00   50
 23  \w    -27.00  21.00   0.50    0.05    --   47.57 -19.00 -60.00   96
 24  \w     37.00 106.00   0.50    0.05    --  107.75 -99.00-150.00  138
 25  \w     53.00  78.00   0.50    0.05    --  107.75-134.00-139.00   50
 26  \w   -119.00 -77.00   0.50    0.05    -- -100.00 135.00 107.00   84
;
_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      0.0980249000
_diffrn_orient_matrix_UB_12      -0.0266898000
_diffrn_orient_matrix_UB_13      0.1679714000
_diffrn_orient_matrix_UB_21      -0.0281178000
_diffrn_orient_matrix_UB_22      -0.0937448000
_diffrn_orient_matrix_UB_23      -0.0474861000
_diffrn_orient_matrix_UB_31      0.0987117000
_diffrn_orient_matrix_UB_32      -0.0003003000
_diffrn_orient_matrix_UB_33      -0.0998193000
_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  0.0145
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9014
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.186
_diffrn_reflns_theta_min         4.075
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28930
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0825P)^2^+0.2168P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1466
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2478
_reflns_number_total             2719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00126h2.cif
_cod_data_source_block           5-II
_cod_original_cell_volume        1368.53(5)
_cod_database_code               7244640
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.968
_reflns_odcompleteness_completeness 99.30
_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), C11(H11), C13(H13), C6(H6), C12(H12), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C8(H8A,H8B,H8C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              42363
_shelx_hkl_checksum              97072
_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 2.971
_oxdiff_exptl_absorpt_empirical_full_min 0.794