#------------------------------------------------------------------------------
#$Date: 2023-07-21 04:15:44 +0300 (Fri, 21 Jul 2023) $
#$Revision: 285306 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/70/7247085.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_7247085
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         'C15 H15 N O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.188(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8609(4)
_cell_length_b                   21.0733(11)
_cell_length_c                   10.4926(6)
_cell_measurement_reflns_used    4561
_cell_measurement_temperature    301.97(10)
_cell_measurement_theta_max      29.6780
_cell_measurement_theta_min      1.9550
_cell_volume                     1292.46(13)
_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      301.97(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.801
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  21.00   1.00    0.80    --   -6.53 -99.00-180.00   32
  2  ω     -5.00  20.00   1.00    0.80    --   -6.53 -99.00 -90.00   25
  3  ω     -7.00  26.00   1.00    0.80    --   -6.53 -99.00   0.00   33
  4  ω      2.00  27.00   1.00    0.80    --   -6.53 -99.00  30.00   25
  5  ω    -68.00  16.00   1.00    0.80    --    3.64 -49.00 169.00   84
  6  ω      8.00  76.00   1.00    0.80    --    3.64  49.00 -42.00   68
;
_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      -0.1088773000
_diffrn_orient_matrix_UB_12      -0.0095972000
_diffrn_orient_matrix_UB_13      -0.0272092000
_diffrn_orient_matrix_UB_21      0.0534255000
_diffrn_orient_matrix_UB_22      -0.0175795000
_diffrn_orient_matrix_UB_23      -0.0471731000
_diffrn_orient_matrix_UB_31      0.0039274000
_diffrn_orient_matrix_UB_32      -0.0270587000
_diffrn_orient_matrix_UB_33      0.0403427000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.801
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11973
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.801
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.736
_diffrn_reflns_theta_min         1.933
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88898
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.015(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   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0469
_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)+(0.0638P)²+0.1251P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1395
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2102
_reflns_number_total             3229
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra04102f2.cif
_cod_data_source_block           7
_cod_database_code               7247085
_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 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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(H1), C2(H2A), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12)
2.b Tetrahedral OH refined with riding coordinates:
 O2(H2)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_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 1.273
_oxdiff_exptl_absorpt_empirical_full_min 0.714
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 0.1895(2) 0.44878(6) 0.07176(10) 0.0689(4) Uani 1 1 d . . . . .
O2 O -0.1221(2) 0.49085(7) 0.14687(12) 0.0822(4) Uani 1 1 d . . . . .
H2 H -0.140801 0.503072 0.072648 0.123 Uiso 1 1 calc R U . . .
N1 N 0.2790(2) 0.34870(6) 0.64517(12) 0.0587(4) Uani 1 1 d . . . . .
H1 H 0.178894 0.353904 0.700268 0.070 Uiso 1 1 calc R U . . .
C1 C 0.2293(2) 0.37462(6) 0.52619(13) 0.0451(3) Uani 1 1 d . . . . .
C2 C 0.3819(2) 0.37146(7) 0.43056(13) 0.0481(4) Uani 1 1 d . . . . .
H2A H 0.522284 0.351294 0.446221 0.058 Uiso 1 1 calc R U . . .
C3 C 0.3245(3) 0.39828(7) 0.31273(14) 0.0498(4) Uani 1 1 d . . . . .
H3 H 0.427085 0.395772 0.249359 0.060 Uiso 1 1 calc R U . . .
C4 C 0.1165(2) 0.42898(6) 0.28668(13) 0.0451(3) Uani 1 1 d . . . . .
C5 C -0.0335(2) 0.43267(7) 0.38312(14) 0.0519(4) Uani 1 1 d . . . . .
H5 H -0.172505 0.453623 0.367861 0.062 Uiso 1 1 calc R U . . .
C6 C 0.0206(3) 0.40588(8) 0.50003(15) 0.0540(4) Uani 1 1 d . . . . .
H6 H -0.082708 0.408472 0.563036 0.065 Uiso 1 1 calc R U . . .
C7 C 0.0604(3) 0.45700(7) 0.16059(14) 0.0518(4) Uani 1 1 d . . . . .
C8 C 0.4791(2) 0.31417(7) 0.68618(13) 0.0463(3) Uani 1 1 d . . . . .
C9 C 0.5130(3) 0.25335(7) 0.63875(14) 0.0505(4) Uani 1 1 d . . . . .
C10 C 0.7078(3) 0.22057(8) 0.68472(16) 0.0603(4) Uani 1 1 d . . . . .
H10 H 0.735688 0.180381 0.652669 0.072 Uiso 1 1 calc R U . . .
C11 C 0.8599(3) 0.24611(9) 0.77626(17) 0.0644(5) Uani 1 1 d . . . . .
H11 H 0.987961 0.223124 0.806648 0.077 Uiso 1 1 calc R U . . .
C12 C 0.8219(3) 0.30600(9) 0.82296(15) 0.0623(4) Uani 1 1 d . . . . .
H12 H 0.924642 0.323019 0.885556 0.075 Uiso 1 1 calc R U . . .
C13 C 0.6337(3) 0.34123(7) 0.77836(14) 0.0533(4) Uani 1 1 d . . . . .
C14 C 0.3420(3) 0.22289(9) 0.54349(17) 0.0703(5) Uani 1 1 d . . . . .
H14A H 0.189944 0.234248 0.563294 0.106 Uiso 1 1 calc R U . . .
H14B H 0.358933 0.177605 0.547417 0.106 Uiso 1 1 calc R U . . .
H14C H 0.368087 0.237401 0.459054 0.106 Uiso 1 1 calc R U . . .
C15 C 0.5954(4) 0.40675(9) 0.8302(2) 0.0860(6) Uani 1 1 d . . . . .
H15A H 0.576288 0.436337 0.760628 0.129 Uiso 1 1 calc R U . . .
H15B H 0.725097 0.418935 0.885983 0.129 Uiso 1 1 calc R U . . .
H15C H 0.460555 0.406726 0.876857 0.129 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 0.0033 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
C7 O2 H2 109.5 . . ?
C1 N1 H1 116.8 . . ?
C1 N1 C8 126.46(12) . . ?
C8 N1 H1 116.8 . . ?
N1 C1 C2 122.05(12) . . ?
N1 C1 C6 119.31(13) . . ?
C2 C1 C6 118.63(12) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 C1 119.91(13) . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.36(13) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 118.38(12) . . ?
C3 C4 C7 120.09(13) . . ?
C5 C4 C7 121.53(13) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.83(13) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.87(14) . . ?
C5 C6 H6 119.6 . . ?
O1 C7 O2 122.38(13) . . ?
O1 C7 C4 120.53(13) . . ?
O2 C7 C4 117.08(14) . . ?
C9 C8 N1 119.92(13) . . ?
C9 C8 C13 121.33(13) . . ?
C13 C8 N1 118.68(13) . . ?
C8 C9 C14 121.55(14) . . ?
C10 C9 C8 117.89(14) . . ?
C10 C9 C14 120.54(15) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.53(16) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.67(15) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.13(15) . . ?
C13 C12 H12 119.4 . . ?
C8 C13 C15 121.17(15) . . ?
C12 C13 C8 118.42(15) . . ?
C12 C13 C15 120.39(16) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O1 C7 1.2544(18) . ?
O2 H2 0.8200 . ?
O2 C7 1.2849(18) . ?
N1 H1 0.8600 . ?
N1 C1 1.3742(18) . ?
N1 C8 1.4204(17) . ?
C1 C2 1.394(2) . ?
C1 C6 1.399(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.3786(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(2) . ?
C4 C5 1.390(2) . ?
C4 C7 1.4641(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.366(2) . ?
C6 H6 0.9300 . ?
C8 C9 1.394(2) . ?
C8 C13 1.397(2) . ?
C9 C10 1.390(2) . ?
C9 C14 1.507(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(2) . ?
C13 C15 1.507(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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 C1 C2 C3 -179.89(14) . . . . ?
N1 C1 C6 C5 179.45(14) . . . . ?
N1 C8 C9 C10 -177.96(13) . . . . ?
N1 C8 C9 C14 0.3(2) . . . . ?
N1 C8 C13 C12 176.56(13) . . . . ?
N1 C8 C13 C15 -2.4(2) . . . . ?
C1 N1 C8 C9 -70.8(2) . . . . ?
C1 N1 C8 C13 112.06(18) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C2 C3 C4 C7 180.00(13) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C3 C4 C7 O1 6.3(2) . . . . ?
C3 C4 C7 O2 -172.30(14) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C5 C4 C7 O1 -174.21(14) . . . . ?
C5 C4 C7 O2 7.1(2) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
C7 C4 C5 C6 179.53(14) . . . . ?
C8 N1 C1 C2 -2.5(2) . . . . ?
C8 N1 C1 C6 178.24(14) . . . . ?
C8 C9 C10 C11 1.7(2) . . . . ?
C9 C8 C13 C12 -0.5(2) . . . . ?
C9 C8 C13 C15 -179.50(15) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C8 1.3(2) . . . . ?
C11 C12 C13 C15 -179.74(16) . . . . ?
C13 C8 C9 C10 -0.9(2) . . . . ?
C13 C8 C9 C14 177.39(14) . . . . ?
C14 C9 C10 C11 -176.64(16) . . . . ?
