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#$Date: 2022-03-18 01:41:20 +0200 (Fri, 18 Mar 2022) $
#$Revision: 273760 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/46/7244636.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_7244636
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         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-10-28 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.9732(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8013(2)
_cell_length_b                   6.8401(2)
_cell_length_c                   14.1778(3)
_cell_measurement_reflns_used    2830
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.0
_cell_volume                     1143.78(5)
_computing_cell_refinement       'Denzo-SMN (Nonius, 1997)'
_computing_data_collection       'Collect (Nonius, 2002)'
_computing_data_reduction        'Denzo-SMN (Nonius, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'XP in SHELXTL (Sheldrick, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ=55°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5005
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowsky & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2613
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0810P)²+0.1988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                2058
_reflns_number_total             2613
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d2ce00126h2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               7244636
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.53558(11) 0.5060(2) 0.18949(9) 0.0192(3) Uani 1 1 d . . .
C2 C 0.45880(11) 0.5738(2) 0.11787(9) 0.0195(3) Uani 1 1 d . . .
C3 C 0.36169(12) 0.4655(2) 0.09346(9) 0.0227(3) Uani 1 1 d . . .
H3 H 0.3107 0.5119 0.0452 0.027 Uiso 1 1 calc R . .
C4 C 0.33909(12) 0.2919(2) 0.13880(10) 0.0255(3) Uani 1 1 d . . .
H4 H 0.2726 0.2194 0.1225 0.031 Uiso 1 1 calc R . .
C5 C 0.41501(12) 0.2247(2) 0.20865(10) 0.0252(3) Uani 1 1 d . . .
H5 H 0.3991 0.1055 0.2399 0.030 Uiso 1 1 calc R . .
C6 C 0.51335(12) 0.3261(2) 0.23432(9) 0.0223(3) Uani 1 1 d . . .
N7 N 0.63568(10) 0.60806(18) 0.21481(8) 0.0204(3) Uani 1 1 d . . .
H7 H 0.6583(14) 0.688(2) 0.1722(12) 0.024 Uiso 1 1 d . . .
C8 C 0.65137(11) 0.69398(19) 0.30553(9) 0.0209(3) Uani 1 1 d . . .
C9 C 0.56756(13) 0.6907(2) 0.37258(10) 0.0247(3) Uani 1 1 d . . .
H9 H 0.4980 0.6250 0.3589 0.030 Uiso 1 1 calc R . .
C10 C 0.58518(13) 0.7827(2) 0.45922(10) 0.0283(4) Uani 1 1 d . . .
H10 H 0.5279 0.7782 0.5046 0.034 Uiso 1 1 calc R . .
C11 C 0.68513(13) 0.8805(2) 0.47987(10) 0.0294(4) Uani 1 1 d . . .
H11 H 0.6968 0.9438 0.5390 0.035 Uiso 1 1 calc R . .
C12 C 0.76838(13) 0.8854(2) 0.41328(10) 0.0295(4) Uani 1 1 d . . .
H12 H 0.8372 0.9535 0.4270 0.035 Uiso 1 1 calc R . .
C13 C 0.75255(12) 0.7921(2) 0.32675(10) 0.0250(3) Uani 1 1 d . . .
H13 H 0.8107 0.7953 0.2821 0.030 Uiso 1 1 calc R . .
C14 C 0.47787(11) 0.7610(2) 0.06798(9) 0.0200(3) Uani 1 1 d . . .
O15 O 0.56604(8) 0.85661(15) 0.07584(7) 0.0245(3) Uani 1 1 d . . .
O16 O 0.39157(9) 0.81718(15) 0.01323(7) 0.0290(3) Uani 1 1 d . . .
H16 H 0.4092 0.9190 -0.0160 0.044 Uiso 1 1 calc R . .
C17 C 0.59626(13) 0.2413(2) 0.30602(10) 0.0281(4) Uani 1 1 d . . .
H17A H 0.5912 0.3127 0.3656 0.042 Uiso 1 1 calc R . .
H17B H 0.6733 0.2527 0.2829 0.042 Uiso 1 1 calc R . .
H17C H 0.5784 0.1032 0.3162 0.042 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
N7 C1 C6 118.95(12) . . ?
N7 C1 C2 122.09(12) . . ?
C6 C1 C2 118.91(12) . . ?
C3 C2 C1 120.22(12) . . ?
C3 C2 C14 118.40(12) . . ?
C1 C2 C14 121.38(12) . . ?
C4 C3 C2 120.67(13) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.07(13) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 122.24(13) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C1 118.86(13) . . ?
C5 C6 C17 120.21(13) . . ?
C1 C6 C17 120.89(13) . . ?
C1 N7 C8 121.20(11) . . ?
C1 N7 H7 114.3(11) . . ?
C8 N7 H7 109.8(11) . . ?
C13 C8 C9 118.87(13) . . ?
C13 C8 N7 118.61(12) . . ?
C9 C8 N7 122.47(13) . . ?
C10 C9 C8 120.46(14) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.56(14) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.23(14) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C13 120.88(14) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 120.00(13) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
O15 C14 O16 122.21(12) . . ?
O15 C14 C2 123.85(12) . . ?
O16 C14 C2 113.95(11) . . ?
C14 O16 H16 109.5 . . ?
C6 C17 H17A 109.5 . . ?
C6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
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
C1 N7 1.4080(17) . ?
C1 C6 1.4139(19) . ?
C1 C2 1.4155(18) . ?
C2 C3 1.3979(19) . ?
C2 C14 1.4842(19) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3906(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 C17 1.5028(19) . ?
N7 C8 1.4204(17) . ?
N7 H7 0.864(17) . ?
C8 C13 1.3937(19) . ?
C8 C9 1.395(2) . ?
C9 C10 1.390(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O15 1.2306(16) . ?
C14 O16 1.3164(16) . ?
O16 H16 0.8400 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N7 C1 C2 C3 178.52(11) . . . . ?
C6 C1 C2 C3 1.2(2) . . . . ?
N7 C1 C2 C14 -2.4(2) . . . . ?
C6 C1 C2 C14 -179.72(11) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C14 C2 C3 C4 -178.95(12) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C1 1.6(2) . . . . ?
C4 C5 C6 C17 -176.25(13) . . . . ?
N7 C1 C6 C5 -179.45(12) . . . . ?
C2 C1 C6 C5 -2.01(19) . . . . ?
N7 C1 C6 C17 -1.6(2) . . . . ?
C2 C1 C6 C17 175.80(12) . . . . ?
C6 C1 N7 C8 -68.26(17) . . . . ?
C2 C1 N7 C8 114.38(14) . . . . ?
C1 N7 C8 C13 179.59(12) . . . . ?
C1 N7 C8 C9 -3.1(2) . . . . ?
C13 C8 C9 C10 -0.4(2) . . . . ?
N7 C8 C9 C10 -177.70(13) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C11 C12 C13 C8 0.8(2) . . . . ?
C9 C8 C13 C12 -0.3(2) . . . . ?
N7 C8 C13 C12 177.05(13) . . . . ?
C3 C2 C14 O15 -171.36(12) . . . . ?
C1 C2 C14 O15 9.5(2) . . . . ?
C3 C2 C14 O16 8.27(18) . . . . ?
C1 C2 C14 O16 -170.87(12) . . . . ?
