#------------------------------------------------------------------------------
#$Date: 2023-07-21 03:15:44 +0200 (Fri 21 de Jul de 2023) $
#$Revision: 285306 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/70/7247080.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_7247080
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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_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                80.106(4)
_cell_angle_beta                 85.810(3)
_cell_angle_gamma                73.682(4)
_cell_formula_units_Z            2
_cell_length_a                   5.8469(2)
_cell_length_b                   6.4881(3)
_cell_length_c                   15.9753(7)
_cell_measurement_reflns_used    3784
_cell_measurement_temperature    302.99(10)
_cell_measurement_theta_max      75.5690
_cell_measurement_theta_min      5.6100
_cell_volume                     572.77(4)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00  91.00   0.50    0.05    --   46.32  62.00 100.00  116
  2  ω     89.00 174.00   0.50    0.05    --  104.25  62.00 100.00  170
  3  ω    136.00 177.00   0.50    0.05    --  104.25  15.00  30.00   82
  4  ω     91.00 128.00   0.50    0.05    --  104.25  15.00  30.00   74
  5  ω    110.00 175.00   0.50    0.05    --  104.25  45.00-120.00  130
  6  ω    -24.00  29.00   0.50    0.05    --  -46.32  19.00  30.00  106
  7  ω    -62.00 -28.00   0.50    0.05    --  -46.32  62.00 100.00   68
  8  ω    -19.00   6.00   0.50    0.05    --  -46.32  62.00 100.00   50
  9  ω    -22.00   6.00   0.50    0.05    --   46.32 -62.00 -37.00   56
 10  ω    -28.00  29.00   0.50    0.05    --   46.32 -19.00-180.00  114
 11  ω     19.00  49.00   0.50    0.05    --   46.32 -62.00 -37.00   60
 12  ω     59.00 103.00   0.50    0.05    --  104.25 -77.00-120.00   88
 13  ω     41.00  66.00   0.50    0.05    --  104.25 -62.00 -37.00   50
 14  ω     77.00 103.00   0.50    0.05    --  104.25 -77.00  60.00   52
 15  ω     34.00  65.00   0.50    0.05    --  104.25 -61.00 120.00   62
 16  ω     33.00  58.00   0.50    0.05    --  104.25 -61.00  90.00   50
 17  ω     33.00  70.00   0.50    0.05    --  104.25 -77.00  60.00   74
 18  ω     32.00  76.00   0.50    0.05    --  104.25 -94.00  30.00   88
 19  ω     70.00  95.00   0.50    0.05    --  104.25 -94.00  60.00   50
 20  ω     87.00 112.00   0.50    0.05    --  104.25-125.00 -30.00   50
 21  ω     44.00  89.00   0.50    0.05    --  104.25 -94.00 -30.00   90
 22  ω     32.00  64.00   0.50    0.05    --  104.25-125.00 -30.00   64
 23  ω     40.00  65.00   0.50    0.05    --  104.25-125.00 -60.00   50
 24  ω     69.00 104.00   0.50    0.05    --  104.25-125.00 -60.00   70
 25  ω   -124.00 -87.00   0.50    0.05    -- -102.00 142.00  -8.68   74
 26  ω    -70.00 -36.00   0.50    0.05    -- -102.00  62.00 100.00   68
 27  ω    -62.00 -29.00   0.50    0.05    -- -102.00 125.00 120.00   66
 28  ω   -112.00 -79.00   0.50    0.05    -- -102.00 125.00 150.00   66
 29  ω    -64.00 -34.00   0.50    0.05    -- -102.00  61.00 -90.00   60
 30  ω    -69.00 -44.00   0.50    0.05    -- -102.00  61.00-150.00   50
 31  ω   -117.00 -78.00   0.50    0.05    --  -46.32 -62.00 -37.00   78
 32  ω    -72.00 -32.00   0.50    0.05    --  -46.32 -62.00 -37.00   80
 33  ω   -120.00 -94.00   0.50    0.05    -- -102.00 -62.00 -37.00   52
 34  ω   -160.00-134.00   0.50    0.05    -- -102.00 -62.00 -37.00   52
 35  ω   -175.00-141.00   0.50    0.05    -- -102.00 -30.00  30.00   68
 36  ω   -133.00 -94.00   0.50    0.05    -- -102.00 -30.00  30.00   78
 37  ω   -106.00 -81.00   0.50    0.05    --  -46.32-125.00  90.00   50
 38  ω   -174.00-102.00   0.50    0.05    -- -102.00-125.00  90.00  144
;
_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      0.1330325000
_diffrn_orient_matrix_UB_12      0.1435919000
_diffrn_orient_matrix_UB_13      -0.0595854000
_diffrn_orient_matrix_UB_21      -0.2395204000
_diffrn_orient_matrix_UB_22      0.1468909000
_diffrn_orient_matrix_UB_23      -0.0356158000
_diffrn_orient_matrix_UB_31      -0.0189501000
_diffrn_orient_matrix_UB_32      0.1434763000
_diffrn_orient_matrix_UB_33      0.0690657000
_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  0.0264
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5721
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.268
_diffrn_reflns_theta_min         5.624
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49211
_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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.018(3)
_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   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2255
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0432
_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)+(0.0775P)²+0.0528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1350
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1950
_reflns_number_total             2255
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra04102f2.cif
_cod_data_source_block           4
_cod_database_code               7247080
_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.
;
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.925
_reflns_odcompleteness_completeness 99.36
_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
2. Restrained distances
 O1-H1
 0.86 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C12(H12), C13(H13), C9(H9), C10(H10), C2(H2), C6(H6), C3(H3), C5(H5)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_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 2.406
_oxdiff_exptl_absorpt_empirical_full_min 0.258
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_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
O2 O 1.16516(18) -0.35992(15) 0.43380(7) 0.0538(3) Uani 1 1 d . . . . .
O1 O 0.78252(19) -0.25550(17) 0.47446(7) 0.0565(3) Uani 1 1 d D . . . .
N1 N 0.8969(2) 0.63224(19) 0.25824(8) 0.0504(3) Uani 1 1 d . . . . .
H1A H 1.017999 0.679929 0.262603 0.061 Uiso 1 1 calc R U . . .
C8 C 0.9080(2) 0.4236(2) 0.30131(8) 0.0414(3) Uani 1 1 d . . . . .
C12 C 0.7314(2) 0.1658(2) 0.38928(8) 0.0431(3) Uani 1 1 d . . . . .
H12 H 0.599199 0.133376 0.418494 0.052 Uiso 1 1 calc R U . . .
C11 C 0.9467(2) 0.0047(2) 0.38960(7) 0.0397(3) Uani 1 1 d . . . . .
C13 C 0.7118(2) 0.3729(2) 0.34623(8) 0.0452(3) Uani 1 1 d . . . . .
H13 H 0.567209 0.479298 0.347082 0.054 Uiso 1 1 calc R U . . .
C9 C 1.1245(2) 0.2634(2) 0.30287(8) 0.0452(3) Uani 1 1 d . . . . .
H9 H 1.257011 0.296275 0.274035 0.054 Uiso 1 1 calc R U . . .
C14 C 0.9682(2) -0.2173(2) 0.43515(8) 0.0416(3) Uani 1 1 d . . . . .
C10 C 1.1448(2) 0.0566(2) 0.34668(8) 0.0443(3) Uani 1 1 d . . . . .
H10 H 1.290781 -0.048386 0.347628 0.053 Uiso 1 1 calc R U . . .
C1 C 0.7109(2) 0.7726(2) 0.20874(8) 0.0421(3) Uani 1 1 d . . . . .
C2 C 0.7150(3) 0.9877(2) 0.18238(8) 0.0479(4) Uani 1 1 d . . . . .
H2 H 0.834397 1.037220 0.200726 0.057 Uiso 1 1 calc R U . . .
C6 C 0.5288(3) 0.7051(2) 0.18037(9) 0.0489(3) Uani 1 1 d . . . . .
H6 H 0.523034 0.561921 0.196598 0.059 Uiso 1 1 calc R U . . .
C3 C 0.5430(3) 1.1278(2) 0.12919(9) 0.0524(4) Uani 1 1 d . . . . .
H3 H 0.551283 1.269749 0.111370 0.063 Uiso 1 1 calc R U . . .
C5 C 0.3557(3) 0.8494(3) 0.12810(9) 0.0536(4) Uani 1 1 d . . . . .
H5 H 0.234538 0.800938 0.110434 0.064 Uiso 1 1 calc R U . . .
C4 C 0.3576(3) 1.0634(2) 0.10141(9) 0.0529(4) Uani 1 1 d . . . . .
C7 C 0.1682(4) 1.2214(3) 0.04533(12) 0.0748(5) Uani 1 1 d . . . . .
H7A H 0.067077 1.324734 0.077876 0.112 Uiso 1 1 calc R U . . .
H7B H 0.074528 1.143566 0.023417 0.112 Uiso 1 1 calc R U . . .
H7C H 0.242323 1.296508 -0.001031 0.112 Uiso 1 1 calc R U . . .
H1 H 0.812(7) -0.383(3) 0.507(2) 0.187(15) Uiso 1 1 d 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 113(3) . . ?
C8 N1 H1A 116.3 . . ?
C8 N1 C1 127.31(12) . . ?
C1 N1 H1A 116.3 . . ?
N1 C8 C13 122.09(12) . . ?
C9 C8 N1 118.93(12) . . ?
C9 C8 C13 118.91(12) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C13 C12 C11 120.83(12) . . ?
C12 C11 C14 121.02(12) . . ?
C12 C11 C10 118.98(12) . . ?
C10 C11 C14 120.00(12) . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.27(12) . . ?
C12 C13 H13 119.9 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.80(12) . . ?
C10 C9 H9 119.6 . . ?
O2 C14 O1 122.99(12) . . ?
O2 C14 C11 119.49(12) . . ?
O1 C14 C11 117.52(11) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 C11 120.18(12) . . ?
C9 C10 H10 119.9 . . ?
C2 C1 N1 118.64(13) . . ?
C6 C1 N1 123.18(12) . . ?
C6 C1 C2 118.07(13) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.43(14) . . ?
C3 C2 H2 119.8 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.55(13) . . ?
C5 C6 H6 119.7 . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.11(13) . . ?
C4 C3 H3 118.9 . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 121.98(14) . . ?
C4 C5 H5 119.0 . . ?
C3 C4 C7 121.04(15) . . ?
C5 C4 C3 116.85(13) . . ?
C5 C4 C7 122.12(16) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
O2 C14 1.2601(16) . ?
O1 C14 1.2776(17) . ?
O1 H1 0.876(10) . ?
N1 H1A 0.8600 . ?
N1 C8 1.3957(17) . ?
N1 C1 1.3996(17) . ?
C8 C13 1.3963(19) . ?
C8 C9 1.3926(19) . ?
C12 H12 0.9300 . ?
C12 C11 1.3917(18) . ?
C12 C13 1.3775(19) . ?
C11 C14 1.4733(18) . ?
C11 C10 1.3962(19) . ?
C13 H13 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.3799(19) . ?
C10 H10 0.9300 . ?
C1 C2 1.3929(19) . ?
C1 C6 1.390(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.386(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.384(2) . ?
C4 C7 1.507(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
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 C8 C13 C12 -178.73(12) . . . . ?
N1 C8 C9 C10 178.20(11) . . . . ?
N1 C1 C2 C3 176.00(12) . . . . ?
N1 C1 C6 C5 -176.87(13) . . . . ?
C8 N1 C1 C2 169.48(13) . . . . ?
C8 N1 C1 C6 -14.3(2) . . . . ?
C8 C9 C10 C11 0.6(2) . . . . ?
C12 C11 C14 O2 179.57(11) . . . . ?
C12 C11 C14 O1 -0.29(19) . . . . ?
C12 C11 C10 C9 -1.71(19) . . . . ?
C11 C12 C13 C8 0.7(2) . . . . ?
C13 C8 C9 C10 1.2(2) . . . . ?
C13 C12 C11 C14 -179.65(11) . . . . ?
C13 C12 C11 C10 1.1(2) . . . . ?
C9 C8 C13 C12 -1.8(2) . . . . ?
C14 C11 C10 C9 179.01(11) . . . . ?
C10 C11 C14 O2 -1.17(19) . . . . ?
C10 C11 C14 O1 178.97(11) . . . . ?
C1 N1 C8 C13 -41.7(2) . . . . ?
C1 N1 C8 C9 141.36(14) . . . . ?
C1 C2 C3 C4 1.4(2) . . . . ?
C1 C6 C5 C4 0.7(2) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
C2 C3 C4 C7 178.27(14) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
C6 C5 C4 C3 0.3(2) . . . . ?
C6 C5 C4 C7 -179.34(14) . . . . ?
