#------------------------------------------------------------------------------
#$Date: 2023-07-21 04:15:44 +0300 (Fri, 21 Jul 2023) $
#$Revision: 285306 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/70/7247081.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_7247081
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         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_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             2021-08-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.919(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5689(6)
_cell_length_b                   5.8946(2)
_cell_length_c                   14.9692(8)
_cell_measurement_reflns_used    3414
_cell_measurement_temperature    302.98(10)
_cell_measurement_theta_max      76.2460
_cell_measurement_theta_min      4.0800
_cell_volume                     1182.81(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.98(10)
_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 0.937
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00 118.00   0.50    0.05    --   46.07  77.00-150.00  186
  2  ω     70.00 105.00   0.50    0.05    --   46.07 151.00  20.00   70
  3  ω    111.00 137.00   0.50    0.14    --  104.25 122.00-140.00   52
  4  ω     91.00 174.00   0.50    0.14    --  104.25  61.00-150.00  166
  5  ω     33.00  62.00   0.50    0.14    --  104.25 -61.00 -90.00   58
  6  ω     34.00 101.00   0.50    0.14    --  104.25 -94.00 -30.00  134
  7  ω     82.00 112.00   0.50    0.14    --  104.25-125.00-120.00   60
  8  ω     32.00 129.00   0.50    0.14    --  104.25-151.00 -23.00  194
  9  ω     53.00  90.00   0.50    0.05    --   46.07-122.00 137.00   74
 10  ω     68.00 105.00   0.50    0.14    --  104.25-122.00 137.00   74
 11  ω     39.00 106.00   0.50    0.14    --  104.25 -94.00 120.00  134
 12  ω    -23.00  29.00   0.50    0.05    --  -46.07  19.00 -90.00  104
 13  ω    -68.00 -34.00   0.50    0.14    -- -102.00  61.00-180.00   68
 14  ω    -76.00 -51.00   0.50    0.05    --  -46.07 122.00-140.00   50
 15  ω    -63.00 -37.00   0.50    0.14    -- -102.00  61.00  30.00   52
 16  ω    -66.00 -38.00   0.50    0.14    -- -102.00  61.00  60.00   56
 17  ω   -117.00 -91.00   0.50    0.14    -- -102.00 -30.00  30.00   52
 18  ω   -174.00-139.00   0.50    0.14    -- -102.00 -30.00  30.00   70
 19  ω   -150.00-125.00   0.50    0.14    -- -102.00-122.00 137.00   50
 20  ω   -164.00 -80.00   0.50    0.14    -- -102.00 -77.00  60.00  168
 21  ω   -118.00 -57.00   0.50    0.05    --  -46.07-151.00 -23.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0122328000
_diffrn_orient_matrix_UB_12      0.2598183000
_diffrn_orient_matrix_UB_13      -0.0040459000
_diffrn_orient_matrix_UB_21      -0.0504485000
_diffrn_orient_matrix_UB_22      -0.0066350000
_diffrn_orient_matrix_UB_23      0.0853320000
_diffrn_orient_matrix_UB_31      0.1025068000
_diffrn_orient_matrix_UB_32      0.0273611000
_diffrn_orient_matrix_UB_33      0.0596790000
_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  0.0339
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6940
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.409
_diffrn_reflns_theta_min         4.093
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0032(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0519
_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/[σ²(Fo²)+(0.0912P)²+0.1056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1678
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1719
_reflns_number_total             2334
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra04102f2.cif
_cod_data_source_block           3
_cod_database_code               7247081
_shelx_shelxl_version_number     2018/1
_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.
;
_reflns_odcompleteness_completeness 98.93
_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(H1A), C2(H2), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.c 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 2.102
_oxdiff_exptl_absorpt_empirical_full_min 0.511
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 0.07226(11) 0.2588(3) 0.50261(12) 0.0959(5) Uani 1 1 d . . . . .
H1 H 0.020975 0.193705 0.480102 0.144 Uiso 1 1 calc R U . . .
O2 O 0.09889(11) -0.0764(2) 0.57032(10) 0.0897(5) Uani 1 1 d . . . . .
N1 N 0.49448(13) 0.4364(3) 0.74163(13) 0.0905(6) Uani 1 1 d . . . . .
H1A H 0.521956 0.341083 0.781357 0.109 Uiso 1 1 calc R U . . .
C1 C 0.54788(13) 0.6413(3) 0.73645(14) 0.0736(5) Uani 1 1 d . . . . .
C2 C 0.56488(14) 0.7315(3) 0.65511(14) 0.0764(5) Uani 1 1 d . . . . .
H2 H 0.539436 0.658389 0.601420 0.092 Uiso 1 1 calc R U . . .
C3 C 0.61982(14) 0.9313(3) 0.65234(14) 0.0764(5) Uani 1 1 d . . . . .
C4 C 0.65835(14) 1.0332(3) 0.73289(16) 0.0823(6) Uani 1 1 d . . . . .
H4 H 0.695201 1.166049 0.732128 0.099 Uiso 1 1 calc R U . . .
C5 C 0.64375(16) 0.9439(4) 0.81382(16) 0.0876(6) Uani 1 1 d . . . . .
H5 H 0.671160 1.014488 0.867518 0.105 Uiso 1 1 calc R U . . .
C6 C 0.58817(15) 0.7484(4) 0.81586(15) 0.0833(6) Uani 1 1 d . . . . .
H6 H 0.577770 0.688273 0.871080 0.100 Uiso 1 1 calc R U . . .
C7 C 0.6361(2) 1.0321(5) 0.56390(17) 0.1151(9) Uani 1 1 d . . . . .
H7A H 0.599321 1.171317 0.553823 0.173 Uiso 1 1 calc R U . . .
H7B H 0.613569 0.927606 0.515892 0.173 Uiso 1 1 calc R U . . .
H7C H 0.705881 1.062094 0.565327 0.173 Uiso 1 1 calc R U . . .
C8 C 0.40584(13) 0.3673(3) 0.69300(13) 0.0707(5) Uani 1 1 d . . . . .
C9 C 0.34670(14) 0.5016(3) 0.62869(14) 0.0722(5) Uani 1 1 d . . . . .
H9 H 0.369232 0.644131 0.614528 0.087 Uiso 1 1 calc R U . . .
C10 C 0.25641(14) 0.4257(3) 0.58658(13) 0.0727(5) Uani 1 1 d . . . . .
H10 H 0.217630 0.519240 0.545091 0.087 Uiso 1 1 calc R U . . .
C11 C 0.22071(13) 0.2095(3) 0.60451(12) 0.0686(5) Uani 1 1 d . . . . .
C12 C 0.27993(14) 0.0768(3) 0.66879(13) 0.0719(5) Uani 1 1 d . . . . .
H12 H 0.257502 -0.066109 0.682699 0.086 Uiso 1 1 calc R U . . .
C13 C 0.36951(14) 0.1514(3) 0.71148(14) 0.0747(5) Uani 1 1 d . . . . .
H13 H 0.407578 0.058465 0.753669 0.090 Uiso 1 1 calc R U . . .
C14 C 0.12666(14) 0.1221(3) 0.55800(13) 0.0734(5) 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
C14 O1 H1 109.5 . . ?
C1 N1 H1A 115.1 . . ?
C8 N1 H1A 115.1 . . ?
C8 N1 C1 129.78(16) . . ?
C2 C1 N1 122.24(19) . . ?
C2 C1 C6 119.02(19) . . ?
C6 C1 N1 118.68(18) . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.89(19) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C7 120.8(2) . . ?
C4 C3 C2 118.28(19) . . ?
C4 C3 C7 120.9(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 H6 119.8 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 124.10(17) . . ?
N1 C8 C13 118.08(17) . . ?
C9 C8 C13 117.76(18) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.74(16) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.40(17) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C14 122.32(17) . . ?
C12 C11 C10 117.54(17) . . ?
C12 C11 C14 120.14(15) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.45(15) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.10(17) . . ?
C12 C13 H13 119.4 . . ?
O1 C14 C11 117.12(16) . . ?
O2 C14 O1 121.27(18) . . ?
O2 C14 C11 121.61(17) . . ?
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 C14 1.301(2) . ?
O2 C14 1.251(2) . ?
N1 H1A 0.8600 . ?
N1 C1 1.417(2) . ?
N1 C8 1.368(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.381(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.398(3) . ?
C3 C4 1.376(3) . ?
C3 C7 1.498(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.363(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.399(3) . ?
C8 C13 1.407(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.363(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.404(2) . ?
C11 C12 1.394(2) . ?
C11 C14 1.450(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.356(3) . ?
C13 H13 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 C1 C2 C3 -178.52(16) . . . . ?
N1 C1 C6 C5 177.66(18) . . . . ?
N1 C8 C9 C10 -176.22(18) . . . . ?
N1 C8 C13 C12 176.87(17) . . . . ?
C1 N1 C8 C9 -3.6(3) . . . . ?
C1 N1 C8 C13 179.38(19) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C1 C2 C3 C7 -178.5(2) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C6 C1 C2 C3 -1.6(3) . . . . ?
C7 C3 C4 C5 179.7(2) . . . . ?
C8 N1 C1 C2 -47.1(3) . . . . ?
C8 N1 C1 C6 136.0(2) . . . . ?
C8 C9 C10 C11 -1.5(3) . . . . ?
C9 C8 C13 C12 -0.4(3) . . . . ?
C9 C10 C11 C12 1.6(3) . . . . ?
C9 C10 C11 C14 -177.60(17) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
C10 C11 C14 O1 -4.6(3) . . . . ?
C10 C11 C14 O2 175.22(18) . . . . ?
C11 C12 C13 C8 0.5(3) . . . . ?
C12 C11 C14 O1 176.20(17) . . . . ?
C12 C11 C14 O2 -3.9(3) . . . . ?
C13 C8 C9 C10 0.9(3) . . . . ?
C14 C11 C12 C13 178.10(17) . . . . ?
