#------------------------------------------------------------------------------
#$Date: 2024-04-05 01:10:06 +0200 (Fri 05 de Apr de 2024) $
#$Revision: 290901 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/81/7248136.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_7248136
loop_
_publ_author_name
'Hussain, Mohammed Noorul'
'Van Meervelt, Luc'
'Van Gerven, Tom'
_publ_section_title
;
 Crystallization of para-aminobenzoic acid forms from specific solvents
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1647
_journal_page_last               1656
_journal_paper_doi               10.1039/D3CE01055D
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C3 H7 N O, C7 H7 N O2'
_chemical_formula_sum            'C10 H14 N2 O3'
_chemical_formula_weight         210.23
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-07-05 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.772(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1603(7)
_cell_length_b                   11.1181(8)
_cell_length_c                   11.9004(9)
_cell_measurement_reflns_used    4010
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.9130
_cell_measurement_theta_min      2.9860
_cell_volume                     1133.22(16)
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00    5.00    --  -17.15 -99.00  90.00   45
  2  ω    -50.00  40.00   1.00    5.00    --   18.87 -57.00 -60.00   90
  3  ω    -50.00  40.00   1.00    5.00    --   18.87 -57.00-180.00   90
  4  ω    -51.00  49.00   1.00    5.00    --   18.87 -77.00  60.00  100
  5  ω    -87.00  13.00   1.00    5.00    --  -17.15 -77.00 -60.00  100
  6  ω    -20.00  10.00   1.00    5.00    --  -17.15 -99.00 150.00   30
  7  ω     -3.00  88.00   1.00    5.00    --   18.87  57.00  90.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0344677000
_diffrn_orient_matrix_UB_12      0.0391649000
_diffrn_orient_matrix_UB_13      -0.0305712000
_diffrn_orient_matrix_UB_21      -0.0201627000
_diffrn_orient_matrix_UB_22      0.0501505000
_diffrn_orient_matrix_UB_23      0.0283550000
_diffrn_orient_matrix_UB_31      0.0725418000
_diffrn_orient_matrix_UB_32      -0.0047044000
_diffrn_orient_matrix_UB_33      0.0482187000
_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  0.0218
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11747
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.433
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0510
_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)+(0.0717P)²+0.2611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1563
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1676
_reflns_number_total             2308
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce01055d2.cif
_cod_data_source_block           cit1001
_cod_depositor_comments          'Adding full bibliography for 7248136.cif.'
_cod_database_code               7248136
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C7 H6 N1 O2'
_chemical_oxdiff_usercomment     'PABA - DMF'
_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   0.977
_shelx_estimated_absorpt_t_min   0.955
_diffrn_oxdiff_ac4_digest_frames
;
01fd32562cb657f2b4fc8b0e6c31a7d0400002732d2
;
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C2(H2A), C3(H3), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_olex2_submission_original_sample_id 'PABA + DMF'
_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 1.569
_oxdiff_exptl_absorpt_empirical_full_min 0.651
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
N2 N 0.2030(2) 0.49049(15) 0.83961(14) 0.0674(5) Uani 1 1 d . . . . .
O3 O 0.2768(2) 0.46884(16) 0.67911(14) 0.0883(5) Uani 1 1 d . . . . .
C8 C 0.2828(3) 0.4395(2) 0.7801(2) 0.0773(6) Uani 1 1 d . . . . .
H8 H 0.348880 0.376358 0.817214 0.093 Uiso 1 1 calc R U . . .
C9 C 0.2128(5) 0.4499(3) 0.9575(3) 0.1296(13) Uani 1 1 d . . . . .
H9A H 0.112108 0.422100 0.954260 0.194 Uiso 1 1 calc R U . . .
H9B H 0.245814 0.515246 1.013570 0.194 Uiso 1 1 calc R U . . .
H9C H 0.286828 0.385303 0.983006 0.194 Uiso 1 1 calc R U . . .
C10 C 0.0925(3) 0.5849(3) 0.7847(2) 0.0963(8) Uani 1 1 d . . . . .
H10A H 0.074143 0.587829 0.700175 0.144 Uiso 1 1 calc R U . . .
H10B H 0.133793 0.660604 0.820803 0.144 Uiso 1 1 calc R U . . .
H10C H -0.003957 0.568882 0.796671 0.144 Uiso 1 1 calc R U . . .
O1 O 0.15364(18) 0.24941(14) 0.46285(14) 0.0785(5) Uani 1 1 d . . . . .
N1 N 0.4009(3) 0.1493(2) 0.03435(19) 0.0795(6) Uani 1 1 d . . . . .
C1 C 0.3707(2) 0.18289(17) 0.13358(16) 0.0576(5) Uani 1 1 d . . . . .
O2 O 0.35887(18) 0.37183(14) 0.51094(13) 0.0733(5) Uani 1 1 d . . . . .
C2 C 0.4627(2) 0.26811(18) 0.21386(17) 0.0622(5) Uani 1 1 d . . . . .
H2A H 0.547853 0.301491 0.199914 0.075 Uiso 1 1 calc R U . . .
C3 C 0.4303(2) 0.30354(18) 0.31269(16) 0.0591(5) Uani 1 1 d . . . . .
H3 H 0.493249 0.360644 0.364615 0.071 Uiso 1 1 calc R U . . .
C4 C 0.3038(2) 0.25497(16) 0.33633(15) 0.0526(4) Uani 1 1 d . . . . .
C5 C 0.2122(2) 0.17051(18) 0.25664(17) 0.0605(5) Uani 1 1 d . . . . .
H5 H 0.127160 0.137310 0.270831 0.073 Uiso 1 1 calc R U . . .
C6 C 0.2437(2) 0.13480(19) 0.15764(17) 0.0627(5) Uani 1 1 d . . . . .
H6 H 0.180115 0.077950 0.105779 0.075 Uiso 1 1 calc R U . . .
C7 C 0.2640(2) 0.29041(17) 0.44084(16) 0.0571(5) Uani 1 1 d . . . . .
H1A H 0.474(3) 0.176(2) 0.020(2) 0.087(8) Uiso 1 1 d . . . . .
H1B H 0.347(3) 0.097(2) -0.018(2) 0.085(8) Uiso 1 1 d . . . . .
H2 H 0.330(3) 0.392(3) 0.572(3) 0.112(10) Uiso 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 0.0033 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
C8 N2 C9 122.3(2) . . ?
C8 N2 C10 120.32(19) . . ?
C10 N2 C9 117.2(2) . . ?
N2 C8 H8 117.5 . . ?
O3 C8 N2 125.0(2) . . ?
O3 C8 H8 117.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 N1 H1A 121.4(18) . . ?
C1 N1 H1B 124.7(16) . . ?
H1A N1 H1B 114(2) . . ?
N1 C1 C2 121.49(19) . . ?
N1 C1 C6 120.9(2) . . ?
C2 C1 C6 117.61(17) . . ?
C7 O2 H2 111.8(19) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 C1 121.36(17) . . ?
C3 C2 H2A 119.3 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.73(18) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C7 122.74(17) . . ?
C5 C4 C3 117.99(16) . . ?
C5 C4 C7 119.27(16) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.62(17) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.69(18) . . ?
C5 C6 H6 119.7 . . ?
O1 C7 O2 121.93(17) . . ?
O1 C7 C4 123.76(18) . . ?
O2 C7 C4 114.31(16) . . ?
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
N2 C8 1.313(3) . ?
N2 C9 1.447(3) . ?
N2 C10 1.443(3) . ?
O3 C8 1.227(3) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O1 C7 1.219(2) . ?
N1 C1 1.357(3) . ?
N1 H1A 0.80(3) . ?
N1 H1B 0.87(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.399(3) . ?
O2 C7 1.325(2) . ?
O2 H2 0.89(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.369(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(2) . ?
C4 C5 1.386(3) . ?
C4 C7 1.469(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.368(3) . ?
C6 H6 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
C9 N2 C8 O3 178.6(3) . . . . ?
C10 N2 C8 O3 3.2(4) . . . . ?
N1 C1 C2 C3 178.7(2) . . . . ?
N1 C1 C6 C5 -178.85(19) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C4 C7 -179.76(17) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C7 O1 179.70(18) . . . . ?
C3 C4 C7 O2 -0.4(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C5 C4 C7 O1 0.2(3) . . . . ?
C5 C4 C7 O2 -179.85(16) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C7 C4 C5 C6 179.68(17) . . . . ?
