#------------------------------------------------------------------------------
#$Date: 2023-07-21 04:15:44 +0300 (Fri, 21 Jul 2023) $
#$Revision: 285306 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/70/7247083.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_7247083
loop_
_publ_author_name
'Liu, Xiaoting'
'Cui, Jingliang'
'Zeng, Qun'
'Fang, Liwen'
'Liang, Peng-Yu'
'Zhou, Pan-Pan'
'Parkin, Sean'
'Li, Tonglei'
'Ruan, Shigang'
'Long, Sihui'
_publ_section_title
;
 Solvatomorphism and first-time observation of acid--acid catemer in
 4-phenylamino-benzoic acids
;
_journal_issue                   30
_journal_name_full               'RSC Advances'
_journal_page_first              21021
_journal_page_last               21035
_journal_paper_doi               10.1039/D3RA04102F
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C13 H11 N O2, C5 H5 N'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-01
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.056(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2172(2)
_cell_length_b                   11.5108(3)
_cell_length_c                   16.6802(5)
_cell_measurement_reflns_used    6961
_cell_measurement_temperature    282(20)
_cell_measurement_theta_max      77.2730
_cell_measurement_theta_min      3.8580
_cell_volume                     1571.58(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      282(20)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     99.00 132.00   0.50    0.05    --  107.75  19.00  30.00   66
  2  ω     99.00 175.00   0.50    0.05    --  107.75  19.00 150.00  152
  3  ω     32.00 112.00   0.50    0.05    --   47.57  10.00-117.00  160
  4  ω     99.00 145.00   0.50    0.05    --  107.75  10.00-117.00   92
  5  ω     35.00  63.00   0.50    0.05    --  107.75 -57.00  60.00   56
  6  ω    -14.00  20.00   0.50    0.05    --   47.57 -19.00 -90.00   68
  7  ω     35.00  63.00   0.50    0.05    --  107.75 -57.00  30.00   56
  8  ω    -26.00   0.00   0.50    0.05    --   47.57 -10.00  69.00   52
  9  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00 150.00   50
 10  ω     61.00 111.00   0.50    0.05    --  107.75-125.00  60.00  100
 11  ω     82.00 112.00   0.50    0.05    --  107.75-125.00   0.00   60
 12  ω     51.00  76.00   0.50    0.05    --  107.75-125.00   0.00   50
 13  ω     72.00  97.00   0.50    0.05    --  107.75 -99.00 -90.00   50
 14  ω    -25.00   0.00   0.50    0.05    --  -47.57  10.00-117.00   50
 15  ω    -68.00 -32.00   0.50    0.05    -- -100.00  57.00-150.00   72
 16  ω   -108.00 -39.00   0.50    0.05    -- -100.00  77.00  30.00  138
 17  ω    -69.00 -29.00   0.50    0.05    -- -100.00  57.00  60.00   80
 18  ω    -64.00 -34.00   0.50    0.05    -- -100.00  57.00  90.00   60
 19  ω    -55.00 -29.00   0.50    0.05    -- -100.00  57.00 150.00   52
 20  ω   -106.00 -35.00   0.50    0.05    -- -100.00  77.00 150.00  142
 21  ω    -92.00 -29.00   0.50    0.05    --  -47.57 125.00  60.00  126
 22  ω   -107.00 -32.00   0.50    0.05    --  -47.57 -10.00  69.00  150
 23  ω   -148.00 -91.00   0.50    0.05    -- -100.00 -10.00  69.00  114
;
_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      -0.0590845000
_diffrn_orient_matrix_UB_12      -0.0178601000
_diffrn_orient_matrix_UB_13      0.0842193000
_diffrn_orient_matrix_UB_21      -0.1787941000
_diffrn_orient_matrix_UB_22      0.0079836000
_diffrn_orient_matrix_UB_23      -0.0361742000
_diffrn_orient_matrix_UB_31      -0.0028260000
_diffrn_orient_matrix_UB_32      -0.1324327000
_diffrn_orient_matrix_UB_33      -0.0134243000
_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  0.0391
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10427
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.495
_diffrn_reflns_theta_min         4.673
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
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    1.235
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0084(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0429
_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)+(0.0645P)²+0.1339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2563
_reflns_number_total             3138
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra04102f2.cif
_cod_data_source_block           1-S
_cod_original_cell_volume        1571.59(8)
_cod_database_code               7247083
_shelx_shelxl_version_number     2019/2
_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   0.949
_shelx_estimated_absorpt_t_min   0.908
_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 O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
  C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.b 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 2.021
_oxdiff_exptl_absorpt_empirical_full_min 0.601
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.55688(12) 0.81311(9) 0.52677(7) 0.0634(3) Uani 1 1 d . . . . .
H1 H 0.469007 0.828786 0.543939 0.095 Uiso 1 1 calc R U . . .
O2 O 0.41431(12) 0.66343(10) 0.47421(7) 0.0675(3) Uani 1 1 d . . . . .
N1 N 1.13645(13) 0.55040(10) 0.37914(7) 0.0528(3) Uani 1 1 d . . . . .
H1A H 1.222240 0.573186 0.408134 0.063 Uiso 1 1 calc R U . . .
C1 C 0.69767(15) 0.67448(11) 0.45666(7) 0.0451(3) Uani 1 1 d . . . . .
C2 C 0.84872(15) 0.71885(12) 0.48646(8) 0.0484(3) Uani 1 1 d . . . . .
H2 H 0.853020 0.777729 0.524765 0.058 Uiso 1 1 calc R U . . .
C3 C 0.99121(15) 0.67725(12) 0.46032(8) 0.0481(3) Uani 1 1 d . . . . .
H3 H 1.090674 0.707446 0.481726 0.058 Uiso 1 1 calc R U . . .
C4 C 0.98890(15) 0.59007(11) 0.40192(7) 0.0450(3) Uani 1 1 d . . . . .
C5 C 0.83753(17) 0.54525(13) 0.37252(9) 0.0597(4) Uani 1 1 d . . . . .
H5 H 0.832485 0.486901 0.333817 0.072 Uiso 1 1 calc R U . . .
C6 C 0.69597(17) 0.58641(13) 0.40014(9) 0.0580(4) Uani 1 1 d . . . . .
H6 H 0.596543 0.554334 0.380388 0.070 Uiso 1 1 calc R U . . .
C7 C 0.54344(15) 0.71526(12) 0.48577(7) 0.0485(3) Uani 1 1 d . . . . .
C8 C 1.16304(15) 0.47747(11) 0.31443(8) 0.0463(3) Uani 1 1 d . . . . .
C9 C 1.07325(18) 0.48668(13) 0.24035(9) 0.0572(4) Uani 1 1 d . . . . .
H9 H 0.990744 0.541906 0.232684 0.069 Uiso 1 1 calc R U . . .
C10 C 1.1062(2) 0.41387(15) 0.17779(10) 0.0695(4) Uani 1 1 d . . . . .
H10 H 1.044920 0.420345 0.128380 0.083 Uiso 1 1 calc R U . . .
C11 C 1.2279(2) 0.33225(15) 0.18769(11) 0.0729(5) Uani 1 1 d . . . . .
H11 H 1.248346 0.282801 0.145643 0.087 Uiso 1 1 calc R U . . .
C12 C 1.3188(2) 0.32457(14) 0.26019(11) 0.0695(4) Uani 1 1 d . . . . .
H12 H 1.402624 0.270209 0.267034 0.083 Uiso 1 1 calc R U . . .
C13 C 1.28796(18) 0.39639(12) 0.32336(9) 0.0570(4) Uani 1 1 d . . . . .
H13 H 1.351362 0.390319 0.372194 0.068 Uiso 1 1 calc R U . . .
N2 N 0.78401(15) 0.63037(11) 0.09266(8) 0.0631(4) Uani 1 1 d . . . . .
C14 C 0.7270(2) 0.70676(15) 0.14223(11) 0.0711(4) Uani 1 1 d . . . . .
H14 H 0.780145 0.777820 0.149459 0.085 Uiso 1 1 calc R U . . .
C15 C 0.5920(2) 0.68572(17) 0.18378(12) 0.0784(5) Uani 1 1 d . . . . .
H15 H 0.554738 0.741647 0.218012 0.094 Uiso 1 1 calc R U . . .
C16 C 0.5148(2) 0.58219(18) 0.17378(12) 0.0830(6) Uani 1 1 d . . . . .
H16 H 0.423758 0.565489 0.201163 0.100 Uiso 1 1 calc R U . . .
C17 C 0.5730(3) 0.50288(18) 0.12278(14) 0.0891(6) Uani 1 1 d . . . . .
H17 H 0.522083 0.431152 0.114741 0.107 Uiso 1 1 calc R U . . .
C18 C 0.7071(2) 0.53006(16) 0.08365(12) 0.0743(5) Uani 1 1 d . . . . .
H18 H 0.746012 0.475295 0.049052 0.089 Uiso 1 1 calc R U . . .
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
C7 O1 H1 109.5 . . ?
C4 N1 H1A 116.2 . . ?
C4 N1 C8 127.70(11) . . ?
C8 N1 H1A 116.2 . . ?
C2 C1 C7 122.07(12) . . ?
C6 C1 C2 117.84(12) . . ?
C6 C1 C7 120.04(11) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.17(12) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.86(12) . . ?
C4 C3 H3 119.6 . . ?
N1 C4 C3 118.12(11) . . ?
N1 C4 C5 123.96(12) . . ?
C5 C4 C3 117.87(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.67(13) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.2 . . ?
C5 C6 C1 121.57(12) . . ?
C5 C6 H6 119.2 . . ?
O1 C7 C1 114.10(11) . . ?
O2 C7 O1 122.22(12) . . ?
O2 C7 C1 123.68(13) . . ?
C9 C8 N1 122.32(12) . . ?
C13 C8 N1 119.05(12) . . ?
C13 C8 C9 118.58(12) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.13(14) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.86(16) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.12(15) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 120.91(15) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.36(14) . . ?
C12 C13 H13 119.8 . . ?
C18 N2 C14 117.49(14) . . ?
N2 C14 H14 118.6 . . ?
N2 C14 C15 122.86(16) . . ?
C15 C14 H14 118.6 . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.78(17) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 H16 120.7 . . ?
C15 C16 C17 118.69(16) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.17(18) . . ?
C18 C17 H17 120.4 . . ?
N2 C18 C17 123.01(17) . . ?
N2 C18 H18 118.5 . . ?
C17 C18 H18 118.5 . . ?
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
O1 H1 0.8200 . ?
O1 C7 1.3173(17) . ?
O2 C7 1.2178(16) . ?
N1 H1A 0.8600 . ?
N1 C4 1.3800(17) . ?
N1 C8 1.3996(16) . ?
C1 C2 1.3928(17) . ?
C1 C6 1.3836(19) . ?
C1 C7 1.4733(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.3713(18) . ?
C3 H3 0.9300 . ?
C3 C4 1.3974(18) . ?
C4 C5 1.3951(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(2) . ?
C6 H6 0.9300 . ?
C8 C9 1.386(2) . ?
C8 C13 1.3857(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.367(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(2) . ?
C13 H13 0.9300 . ?
N2 C14 1.321(2) . ?
N2 C18 1.318(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.353(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.363(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.366(3) . ?
C18 H18 0.9300 . ?
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
N1 C4 C5 C6 177.68(14) . . . . ?
N1 C8 C9 C10 178.84(14) . . . . ?
N1 C8 C13 C12 -178.94(13) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C2 C1 C6 C5 -1.5(2) . . . . ?
C2 C1 C7 O1 15.06(18) . . . . ?
C2 C1 C7 O2 -164.17(13) . . . . ?
C2 C3 C4 N1 -178.87(12) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 N1 C8 C9 39.2(2) . . . . ?
C4 N1 C8 C13 -143.62(14) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
C6 C1 C7 O1 -167.39(12) . . . . ?
C6 C1 C7 O2 13.4(2) . . . . ?
C7 C1 C2 C3 178.01(12) . . . . ?
C7 C1 C6 C5 -179.11(14) . . . . ?
C8 N1 C4 C3 -169.67(12) . . . . ?
C8 N1 C4 C5 13.0(2) . . . . ?
C8 C9 C10 C11 -0.4(2) . . . . ?
C9 C8 C13 C12 -1.7(2) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
C11 C12 C13 C8 0.4(2) . . . . ?
C13 C8 C9 C10 1.7(2) . . . . ?
N2 C14 C15 C16 0.4(3) . . . . ?
C14 N2 C18 C17 0.2(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 N2 -0.1(3) . . . . ?
C18 N2 C14 C15 -0.3(3) . . . . ?
