#------------------------------------------------------------------------------
#$Date: 2025-08-23 01:35:05 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/09/7240987.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_7240987
loop_
_publ_author_name
'Cruz-Cabeza, A. J.'
'Taylor, E.'
'Sugden, I. J.'
'Bowskill, D. H.'
'Wright, S. E.'
'Abdullahi, H.'
'Tulegenov, D.'
'Sadiq, G.'
'Davey, R. J.'
_publ_section_title
;
 Can solvated intermediates inform us about nucleation pathways? The case
 of β-pABA
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00970A
_journal_year                    2020
_chemical_formula_moiety         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_chemical_name_systematic        '4-amino-3-methylbenzoic acid'
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-06-15 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.802(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7033(4)
_cell_length_b                   8.7280(3)
_cell_length_c                   16.1405(7)
_cell_measurement_reflns_used    4590
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      27.7390
_cell_measurement_theta_min      1.8820
_cell_volume                     1500.10(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 -38.00   1.00    1.00    --   19.70  35.00 174.00   27
  2  ω    -43.00 -16.00   1.00    1.00    --   19.70  60.00   0.00   27
  3  ω     10.00 109.00   1.00    1.00    --   19.70  60.00   0.00   99
  4  ω    -69.00 109.00   1.00    1.00    --   19.70  60.00-120.00  178
  5  ω    -45.00 109.00   1.00    1.00    --   19.70  14.00  60.00  154
  6  ω    -62.00  76.00   1.00    1.00    --   19.70  60.00 -90.00  138
  7  ω     28.00  58.00   1.00    1.00    --   19.70  60.00  30.00   30
  8  ω     79.00 104.00   1.00    1.00    --   19.70  60.00  30.00   25
  9  ω     -5.00  20.00   1.00    1.00    --   19.70  35.00 174.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0664492000
_diffrn_orient_matrix_UB_12      -0.0040210000
_diffrn_orient_matrix_UB_13      -0.0070922000
_diffrn_orient_matrix_UB_21      -0.0014128000
_diffrn_orient_matrix_UB_22      -0.0464417000
_diffrn_orient_matrix_UB_23      0.0359759000
_diffrn_orient_matrix_UB_31      -0.0048760000
_diffrn_orient_matrix_UB_32      0.0665612000
_diffrn_orient_matrix_UB_33      0.0246043000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18127
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.001
_diffrn_reflns_theta_min         1.912
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.30c (Rigaku Oxford Diffraction, 2017)
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    1.339
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0506
_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)+(0.0622P)²+0.2535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1437
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2552
_reflns_number_total             3603
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00970a2.cif
_cod_data_source_block           s5120l
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C8 H9 N O2)'
_cod_original_formula_sum        'C16 H18 N2 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     302.32
_cod_database_code               7240987
_shelxl_version_number           2014/6
_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   0.999
_shelx_estimated_absorpt_t_min   0.976
_reflns_odcompleteness_completeness 99.97
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O2(H2), N1(H1A,H1B), O4(H4), N2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C11(H11), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
;
_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 2.735
_oxdiff_exptl_absorpt_empirical_full_min 0.328
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
O2 O 0.48857(10) 0.73070(13) 0.48067(7) 0.0359(3) Uani 1 1 d . . . . .
H2 H 0.5359 0.6735 0.4584 0.054 Uiso 1 1 d R . . . .
O1 O 0.64214(10) 0.71317(13) 0.58504(7) 0.0336(3) Uani 1 1 d . . . . .
N1 N 0.23845(12) 1.13616(15) 0.74056(8) 0.0326(3) Uani 1 1 d . . . . .
H1A H 0.1740 1.1880 0.7156 0.039 Uiso 1 1 d R . . . .
H1B H 0.2695 1.1660 0.7874 0.039 Uiso 1 1 d R . . . .
C2 C 0.46172(13) 0.86461(17) 0.60295(9) 0.0265(3) Uani 1 1 d . . . . .
C3 C 0.34939(14) 0.92786(17) 0.56599(9) 0.0275(3) Uani 1 1 d . . . . .
H3 H 0.3241 0.9065 0.5091 0.033 Uiso 1 1 calc R . . . .
C4 C 0.27435(14) 1.02014(17) 0.60949(9) 0.0266(3) Uani 1 1 d . . . . .
C5 C 0.31250(13) 1.05126(17) 0.69399(9) 0.0261(3) Uani 1 1 d . . . . .
C6 C 0.42514(14) 0.98916(18) 0.73115(10) 0.0289(3) Uani 1 1 d . . . . .
H6 H 0.4513 1.0107 0.7880 0.035 Uiso 1 1 calc R . . . .
C7 C 0.49812(14) 0.89758(18) 0.68652(10) 0.0285(3) Uani 1 1 d . . . . .
H7 H 0.5742 0.8562 0.7127 0.034 Uiso 1 1 calc R . . . .
C1 C 0.53806(14) 0.76404(18) 0.55625(9) 0.0284(3) Uani 1 1 d . . . . .
C8 C 0.15343(15) 1.08589(19) 0.56857(10) 0.0340(4) Uani 1 1 d . . . . .
H8A H 0.1593 1.1979 0.5677 0.051 Uiso 1 1 calc GR . . . .
H8B H 0.0838 1.0552 0.6000 0.051 Uiso 1 1 calc GR . . . .
H8C H 0.1385 1.0473 0.5114 0.051 Uiso 1 1 calc GR . . . .
O3 O 0.63029(10) 0.54907(14) 0.40210(7) 0.0374(3) Uani 1 1 d . . . . .
O4 O 0.78366(10) 0.52714(13) 0.50596(7) 0.0324(3) Uani 1 1 d . . . . .
H4 H 0.7368 0.5833 0.5293 0.049 Uiso 1 1 d R . . . .
N2 N 1.01386(13) 0.13263(15) 0.22768(9) 0.0372(4) Uani 1 1 d . . . . .
H2A H 0.9680 0.0851 0.1833 0.045 Uiso 1 1 d R . . . .
H2B H 1.0700 0.0721 0.2555 0.045 Uiso 1 1 d R . . . .
C10 C 0.80822(13) 0.40003(16) 0.37994(9) 0.0249(3) Uani 1 1 d . . . . .
C11 C 0.76098(13) 0.36631(16) 0.29831(9) 0.0264(3) Uani 1 1 d . . . . .
H11 H 0.6810 0.4055 0.2777 0.032 Uiso 1 1 calc R . . . .
C12 C 0.82665(14) 0.27769(17) 0.24640(10) 0.0277(3) Uani 1 1 d . . . . .
C13 C 0.94423(14) 0.21829(16) 0.27882(10) 0.0285(3) Uani 1 1 d . . . . .
C14 C 0.99255(14) 0.25372(17) 0.36002(10) 0.0304(4) Uani 1 1 d . . . . .
H14 H 1.0728 0.2158 0.3809 0.036 Uiso 1 1 calc R . . . .
C15 C 0.92580(14) 0.34290(17) 0.41055(10) 0.0282(3) Uani 1 1 d . . . . .
H15 H 0.9596 0.3654 0.4659 0.034 Uiso 1 1 calc R . . . .
C9 C 0.73290(14) 0.49727(17) 0.42968(9) 0.0266(3) Uani 1 1 d . . . . .
C16 C 0.77413(17) 0.2445(2) 0.15881(11) 0.0402(4) Uani 1 1 d . . . . .
H16A H 0.6936 0.2976 0.1469 0.060 Uiso 1 1 calc GR . . . .
H16B H 0.7613 0.1339 0.1519 0.060 Uiso 1 1 calc GR . . . .
H16C H 0.8330 0.2803 0.1203 0.060 Uiso 1 1 calc GR . . . .
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
C1 O2 H2 109.5 . . ?
H1A N1 H1B 118.1 . . ?
C5 N1 H1A 119.7 . . ?
C5 N1 H1B 117.9 . . ?
C3 C2 C1 121.23(13) . . ?
C7 C2 C3 118.30(14) . . ?
C7 C2 C1 120.46(13) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.19(14) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 118.59(14) . . ?
C3 C4 C8 121.22(14) . . ?
C5 C4 C8 120.19(14) . . ?
N1 C5 C4 120.65(13) . . ?
N1 C5 C6 119.80(14) . . ?
C6 C5 C4 119.50(14) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.79(14) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.64(14) . . ?
C6 C7 H7 119.7 . . ?
O2 C1 C2 114.76(13) . . ?
O1 C1 O2 121.99(14) . . ?
O1 C1 C2 123.25(14) . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 O4 H4 109.5 . . ?
H2A N2 H2B 113.8 . . ?
C13 N2 H2A 115.4 . . ?
C13 N2 H2B 113.4 . . ?
C11 C10 C15 119.13(14) . . ?
C11 C10 C9 118.24(13) . . ?
C15 C10 C9 122.63(13) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.18(14) . . ?
C12 C11 H11 118.9 . . ?
C11 C12 C13 117.99(14) . . ?
C11 C12 C16 121.02(14) . . ?
C13 C12 C16 120.99(14) . . ?
N2 C13 C12 119.36(15) . . ?
N2 C13 C14 120.59(14) . . ?
C14 C13 C12 119.93(14) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.09(14) . . ?
C15 C14 H14 119.5 . . ?
C10 C15 H15 120.2 . . ?
C14 C15 C10 119.65(14) . . ?
C14 C15 H15 120.2 . . ?
O3 C9 O4 122.25(14) . . ?
O3 C9 C10 122.41(14) . . ?
O4 C9 C10 115.34(13) . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 H2 0.8195 . ?
O2 C1 1.3126(18) . ?
O1 C1 1.2447(18) . ?
N1 H1A 0.8872 . ?
N1 H1B 0.8358 . ?
N1 C5 1.3648(19) . ?
C2 C3 1.400(2) . ?
C2 C7 1.396(2) . ?
C2 C1 1.460(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(2) . ?
C4 C5 1.410(2) . ?
C4 C8 1.506(2) . ?
C5 C6 1.400(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.372(2) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O3 C9 1.2287(18) . ?
O4 H4 0.8198 . ?
O4 C9 1.3205(18) . ?
N2 H2A 0.9251 . ?
N2 H2B 0.8873 . ?
N2 C13 1.386(2) . ?
C10 C11 1.394(2) . ?
C10 C15 1.397(2) . ?
C10 C9 1.465(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(2) . ?
C12 C13 1.412(2) . ?
C12 C16 1.496(2) . ?
C13 C14 1.394(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(2) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
N1 C5 C6 C7 176.94(14) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 C3 C4 C8 -179.53(14) . . . . ?
C3 C2 C7 C6 0.3(2) . . . . ?
C3 C2 C1 O2 -4.5(2) . . . . ?
C3 C2 C1 O1 175.38(14) . . . . ?
C3 C4 C5 N1 -176.97(14) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C7 C2 C3 C4 -0.3(2) . . . . ?
C7 C2 C1 O2 174.15(14) . . . . ?
C7 C2 C1 O1 -5.9(2) . . . . ?
C1 C2 C3 C4 178.42(14) . . . . ?
C1 C2 C7 C6 -178.47(14) . . . . ?
C8 C4 C5 N1 2.5(2) . . . . ?
C8 C4 C5 C6 179.95(14) . . . . ?
N2 C13 C14 C15 177.93(14) . . . . ?
C10 C11 C12 C13 1.1(2) . . . . ?
C10 C11 C12 C16 -179.45(14) . . . . ?
C11 C10 C15 C14 -0.4(2) . . . . ?
C11 C10 C9 O3 0.3(2) . . . . ?
C11 C10 C9 O4 -178.90(13) . . . . ?
C11 C12 C13 N2 -178.23(13) . . . . ?
C11 C12 C13 C14 -2.1(2) . . . . ?
C12 C13 C14 C15 1.8(2) . . . . ?
C13 C14 C15 C10 -0.5(2) . . . . ?
C15 C10 C11 C12 0.1(2) . . . . ?
C15 C10 C9 O3 178.94(14) . . . . ?
C15 C10 C9 O4 -0.2(2) . . . . ?
C9 C10 C11 C12 178.84(13) . . . . ?
C9 C10 C15 C14 -179.10(13) . . . . ?
C16 C12 C13 N2 2.3(2) . . . . ?
C16 C12 C13 C14 178.51(14) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168341541
