#------------------------------------------------------------------------------
#$Date: 2022-03-18 01:41:20 +0200 (Fri, 18 Mar 2022) $
#$Revision: 273760 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/46/7244638.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7244638
loop_
_publ_author_name
'Tao, Yang'
'Liu, Xiaoting'
'Zhoujin, Yunping'
'Zhou, Panpan'
'Parkin, Sean R.'
'Li, Tonglei'
'Guo, Ju'
'Yu, Faquan'
'Long, Sihui'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  27.00   1.00    0.22    --  -47.57  19.00  60.00   55
  2  ω     71.00 114.00   1.00    0.22    --   47.57 139.00-115.00   43
  3  ω     96.00 128.00   1.00    0.89    --  107.75  37.00  60.00   32
  4  ω     36.00  63.00   1.00    0.89    --  107.75 -57.00  60.00   27
  5  ω     51.00  76.00   1.00    0.89    --  107.75-130.00  -2.00   25
  6  ω     45.00  91.00   1.00    0.89    --  107.75-125.00  30.00   46
  7  ω     58.00  85.00   1.00    0.22    --   47.57-139.00-176.00   27
  8  ω     68.00  93.00   1.00    0.89    --  107.75-139.00-176.00   25
  9  ω    -24.00  23.00   1.00    0.22    --   47.57 -19.00-120.00   47
 10  ω    -86.00 -61.00   1.00    0.22    --  -47.57 130.00  69.00   25
 11  ω    -26.00  15.00   1.00    0.22    --   47.57 -19.00 150.00   41
 12  ω    -85.00 -59.00   1.00    0.22    --  -47.57 139.00-115.00   26
 13  ω    -76.00 -51.00   1.00    0.89    -- -100.00 139.00-115.00   25
 14  ω   -120.00 -86.00   1.00    0.89    -- -100.00 136.00-104.61   34
 15  ω    -60.00 -27.00   1.00    0.89    -- -100.00  57.00 -60.00   33
 16  ω    -69.00 -37.00   1.00    0.89    -- -100.00  57.00 -90.00   32
 17  ω    -73.00 -31.00   1.00    0.89    -- -100.00 141.00  49.35   42
 18  ω   -112.00 -48.00   1.00    0.89    -- -100.00 125.00  30.00   64
 19  ω   -112.00 -62.00   1.00    0.89    -- -100.00 125.00   0.00   50
 20  ω   -123.00 -91.00   1.00    0.89    -- -100.00 141.00  49.35   32
 21  ω   -175.00-100.00   1.00    0.89    -- -100.00 -19.00   0.00   75
 22  ω   -150.00-125.00   1.00    0.89    -- -100.00-130.00  -2.00   25
 23  ω   -137.00 -89.00   1.00    0.89    -- -100.00-125.00  60.00   48
 24  ω   -118.00 -74.00   1.00    0.22    --  -47.57-139.00-176.00   44
 25  ω   -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       'ω 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/[σ²(Fo²)+(0.0892P)²+0.4680P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3492(4) 0.0566(2) 0.44040(7) 0.0727(6) Uani 1 1 d . . . . .
H1 H 0.328958 0.051267 0.470779 0.109 Uiso 1 1 calc GR . . . .
O2 O 0.7292(4) -0.0384(2) 0.46166(6) 0.0679(6) Uani 1 1 d . . . . .
N1 N 0.9550(4) -0.1707(2) 0.38453(8) 0.0586(6) Uani 1 1 d . . . . .
H1A H 0.947341 -0.146985 0.415496 0.070 Uiso 1 1 d R . . . .
C1 C 0.9254(5) -0.3082(3) 0.38152(8) 0.0518(6) Uani 1 1 d . . . . .
C2 C 1.0849(5) -0.3856(3) 0.41361(9) 0.0556(6) Uani 1 1 d . . . . .
C3 C 1.0570(6) -0.5224(3) 0.41222(11) 0.0653(7) Uani 1 1 d . . . . .
C4 C 0.8771(7) -0.5795(3) 0.37865(12) 0.0749(8) Uani 1 1 d . . . . .
H4 H 0.861516 -0.670622 0.377212 0.090 Uiso 1 1 calc R . . . .
C5 C 0.7217(6) -0.5022(4) 0.34751(12) 0.0740(8) Uani 1 1 d . . . . .
H5 H 0.601223 -0.541641 0.325298 0.089 Uiso 1 1 calc R . . . .
C6 C 0.7423(5) -0.3670(3) 0.34881(10) 0.0618(7) Uani 1 1 d . . . . .
H6 H 0.634529 -0.315392 0.327984 0.074 Uiso 1 1 calc R . . . .
C7 C 1.2807(6) -0.3201(4) 0.44891(12) 0.0768(9) Uani 1 1 d . . . . .
H7A H 1.384044 -0.258343 0.430601 0.115 Uiso 1 1 calc GR . . . .
H7B H 1.394220 -0.385527 0.463927 0.115 Uiso 1 1 calc GR . . . .
H7C H 1.188650 -0.274698 0.474719 0.115 Uiso 1 1 calc GR . . . .
C8 C 1.2203(7) -0.6095(4) 0.44684(14) 0.0876(10) Uani 1 1 d . . . . .
H8A H 1.403794 -0.595882 0.440855 0.131 Uiso 1 1 calc GR . . . .
H8B H 1.175985 -0.699994 0.440583 0.131 Uiso 1 1 calc GR . . . .
H8C H 1.184932 -0.588063 0.481114 0.131 Uiso 1 1 calc GR . . . .
C9 C 0.8125(5) -0.0809(3) 0.35428(9) 0.0522(6) Uani 1 1 d . . . . .
C10 C 0.6323(5) 0.0071(3) 0.37509(9) 0.0541(6) Uani 1 1 d . . . . .
C11 C 0.5011(6) 0.0985(3) 0.34416(11) 0.0659(7) Uani 1 1 d . . . . .
H11 H 0.381056 0.156369 0.357928 0.079 Uiso 1 1 calc R . . . .
C12 C 0.5476(6) 0.1035(4) 0.29373(11) 0.0741(9) Uani 1 1 d . . . . .
H12 H 0.459321 0.164323 0.273300 0.089 Uiso 1 1 calc R . . . .
C13 C 0.7270(6) 0.0175(3) 0.27352(10) 0.0703(8) Uani 1 1 d . . . . .
H13 H 0.759278 0.022097 0.239359 0.084 Uiso 1 1 calc R . . . .
C14 C 0.8592(5) -0.0746(3) 0.30242(9) 0.0596(7) Uani 1 1 d . . . . .
C15 C 1.0629(6) -0.1620(4) 0.27923(11) 0.0756(9) Uani 1 1 d . . . . .
H15A H 1.222108 -0.159890 0.299480 0.113 Uiso 1 1 calc GR . . . .
H15B H 1.098334 -0.131179 0.246017 0.113 Uiso 1 1 calc GR . . . .
H15C H 0.997711 -0.250650 0.277418 0.113 Uiso 1 1 calc GR . . . .
C16 C 0.5780(5) 0.0060(3) 0.42923(9) 0.0561(6) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C1 124.0(2) . . ?
C2 C1 N1 117.6(2) . . ?
C6 C1 N1 122.0(2) . . ?
C6 C1 C2 120.4(3) . . ?
C1 C2 C7 119.6(3) . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 C7 121.4(3) . . ?
C2 C3 C8 120.9(3) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 C8 119.3(3) . . ?
C5 C4 C3 120.4(3) . . ?
C4 C5 C6 120.8(3) . . ?
C5 C6 C1 119.5(3) . . ?
N1 C9 C10 121.2(2) . . ?
N1 C9 C14 119.6(2) . . ?
C10 C9 C14 119.1(2) . . ?
C9 C10 C16 121.5(2) . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 C16 118.8(3) . . ?
C12 C11 C10 120.7(3) . . ?
C11 C12 C13 119.4(3) . . ?
C14 C13 C12 122.0(3) . . ?
C9 C14 C15 120.7(3) . . ?
C13 C14 C9 119.1(3) . . ?
C13 C14 C15 120.1(3) . . ?
O1 C16 C10 114.1(2) . . ?
O2 C16 O1 121.7(2) . . ?
O2 C16 C10 124.1(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.313(3) . ?
O2 C16 1.225(3) . ?
N1 C1 1.407(4) . ?
N1 C9 1.404(3) . ?
C1 C2 1.402(4) . ?
C1 C6 1.391(4) . ?
C2 C3 1.397(4) . ?
C2 C7 1.504(4) . ?
C3 C4 1.388(4) . ?
C3 C8 1.510(4) . ?
C4 C5 1.375(5) . ?
C5 C6 1.378(4) . ?
C9 C10 1.404(4) . ?
C9 C14 1.409(3) . ?
C10 C11 1.398(4) . ?
C10 C16 1.475(3) . ?
C11 C12 1.371(4) . ?
C12 C13 1.382(5) . ?
C13 C14 1.375(4) . ?
C14 C15 1.509(4) . ?
