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_7244641
_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      orthorhombic
_space_group_IT_number           41
_space_group_name_Hall           'A 2 -2ab'
_space_group_name_H-M_alt        'A e a 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   26.6725(2)
_cell_length_b                   19.70800(10)
_cell_length_c                   10.37290(10)
_cell_measurement_reflns_used    14525
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.2710
_cell_measurement_theta_min      4.4910
_cell_volume                     5452.64(7)
_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    '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 0.990
_diffrn_measured_fraction_theta_max 0.976
_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   -164.00 -89.00   0.50    0.12    -- -100.00 -60.00 117.00  150
  2  \w     -5.00  50.00   0.50    0.05    --   47.57 -60.00 117.00  110
  3  \w    -24.00  11.00   0.50    0.05    --   47.57 -19.00   0.00   70
  4  \w     35.00  60.00   0.50    0.12    --  107.75-100.00  25.00   50
  5  \w     45.00  96.00   0.50    0.12    --  107.75 -77.00  60.00  102
  6  \w     81.00 106.00   0.50    0.12    --  107.75-100.00  25.00   50
  7  \w     40.00 105.00   0.50    0.12    --  107.75 -99.00  60.00  130
  8  \w     35.00  61.00   0.50    0.12    --  107.75 -57.00  60.00   52
  9  \w     38.00  63.00   0.50    0.12    --  107.75 -57.00   0.00   50
 10  \w     35.00  71.00   0.50    0.12    --  107.75 -68.00 -94.00   72
 11  \w     36.00  63.00   0.50    0.12    --  107.75 -57.00 -90.00   54
 12  \w     35.00 103.00   0.50    0.05    --   47.57  37.00-120.00  136
 13  \w     38.00  64.00   0.50    0.12    --  107.75 -60.00 117.00   52
 14  \w    -22.00   3.00   0.50    0.05    --   47.57 -19.00 150.00   50
 15  \w    -69.00 -29.00   0.50    0.12    -- -100.00  57.00-180.00   80
 16  \w     92.00 130.00   0.50    0.12    --  107.75  68.00  38.00   76
 17  \w    -27.00   4.00   0.50    0.05    --  -47.57  19.00 -90.00   62
 18  \w    -26.00  15.00   0.50    0.05    --   47.57 -19.00-120.00   82
 19  \w   -156.00 -98.00   0.50    0.12    -- -100.00 -19.00 -60.00  116
 20  \w    -53.00 -27.00   0.50    0.12    -- -100.00  57.00  30.00   52
 21  \w    108.00 134.00   0.50    0.12    --  107.75  77.00 120.00   52
 22  \w     73.00 100.00   0.50    0.12    --  107.75 -77.00-150.00   54
 23  \w     35.00  60.00   0.50    0.12    --  107.75 -57.00-150.00   50
 24  \w    150.00 175.00   0.50    0.12    --  107.75  77.00 120.00   50
 25  \w     35.00  63.00   0.50    0.12    --  107.75 -57.00-180.00   56
;
_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      0.1041265000
_diffrn_orient_matrix_UB_12      0.0534733000
_diffrn_orient_matrix_UB_13      0.0116210000
_diffrn_orient_matrix_UB_21      0.0126122000
_diffrn_orient_matrix_UB_22      -0.0281673000
_diffrn_orient_matrix_UB_23      0.0536697000
_diffrn_orient_matrix_UB_31      0.1051183000
_diffrn_orient_matrix_UB_32      -0.0495748000
_diffrn_orient_matrix_UB_33      -0.0179307000
_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  0.0162
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16750
_diffrn_reflns_point_group_measured_fraction_full 0.880
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.481
_diffrn_reflns_theta_min         4.487
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58860
_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    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1799 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         4881
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0328
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.634
_reflns_Friedel_fraction_full    0.755
_reflns_Friedel_fraction_max     0.695
_reflns_number_gt                4757
_reflns_number_total             4881
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00126h2.cif
_cod_data_source_block           5-III
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C32 H34 N2 O4'
_cod_original_formula_weight         510.61
_cod_original_formula_moiety         '2(C16 H17 N O2)'
_cod_original_formula_units_Z            8
_cod_original_sg_symbol_Hall     'A 2 -2ac'
_cod_database_code               7244641
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.931
_reflns_odcompleteness_completeness 99.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C19(H19), C20(H20),
 C21(H21), C27(H27), C28(H28), C29(H29)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C23(H23A,H23B,
 H23C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3A)
;
_shelx_res_checksum              75308
_shelx_hkl_checksum              5714
_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 1.348
_oxdiff_exptl_absorpt_empirical_full_min 0.744