#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:52:49 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223640 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/21/7232197.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_7232197
loop_
_publ_author_name
'Ward, Martin R.'
'Younis, Shatha'
'Cruz-Cabeza, Aurora J.'
'Bull, Craig L.'
'Funnell, Nicholas P.'
'Oswald, Iain D. H.'
_publ_section_title
;
 Discovery and recovery of delta p-aminobenzoic acid
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              2058
_journal_paper_doi               10.1039/C8CE01882K
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C7 H7 N O2'
_chemical_formula_sum            'C7 H7 N O2'
_chemical_formula_weight         137.14
_chemical_name_systematic        'p-aminobenzoic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-01 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.667(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4342(10)
_cell_length_b                   4.6146(4)
_cell_length_c                   10.5397(10)
_cell_measurement_reflns_used    498
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.333
_cell_measurement_theta_min      3.934
_cell_volume                     307.53(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.570
_diffrn_measured_fraction_theta_max 0.570
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.570
_diffrn_reflns_Laue_measured_fraction_max 0.570
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1444
_diffrn_reflns_point_group_measured_fraction_full 0.533
_diffrn_reflns_point_group_measured_fraction_max 0.533
_diffrn_reflns_theta_full        23.201
_diffrn_reflns_theta_max         23.201
_diffrn_reflns_theta_min         3.935
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1150 before and 0.0458 after correction. The Ratio of minimum to maximum transmission is 0.8491. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       block
_exptl_crystal_F_000             144
_exptl_crystal_recrystallization_method
'Recrystallised from a supersaturated solution at 0.33 GPa'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 156 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         471
_refine_ls_number_restraints     71
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0410
_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)+(0.0466P)²+0.1530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.1066
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.497
_reflns_Friedel_fraction_max     0.497
_reflns_number_gt                396
_reflns_number_total             471
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL paba04 in Pn
    paba04.res
    created by SHELXL-2016/6 at 14:59:29 on 01-Nov-2018
REM acta 52
CELL 0.71073 6.4342 4.6146 10.5397 90 100.667 90
ZERR 2 0.001 0.0004 0.001 0 0.0089 0
LATT -1
SYMM 0.5+X,-Y,0.5+Z
SFAC C H N O
UNIT 14 14 2 4
RIGU

L.S. 99 0 0
PLAN  20
SIZE 0.15 0.075 0.05
TEMP 23
BOND $H
list 4
MORE -1
CONF
fmap 2 53
acta
OMIT 4 0 6
OMIT 5 -3 -1
REM <olex2.extras>
REM <HklSrc "%.\\paba04.hkl">
REM </olex2.extras>

WGHT    0.046600    0.153000
FVAR       0.58558
O2    4    0.814472    0.698479    0.451022    11.00000    0.04414    0.05539 =
         0.06748    0.01376    0.00239   -0.00550
O1    4    0.503703    0.792288    0.327043    11.00000    0.04611    0.05533 =
         0.03685    0.01220   -0.00003   -0.01058
AFIX 147
H1    2    0.579130    0.884198    0.286719    11.00000   -1.50000
AFIX   0
C7    1    0.622866    0.651593    0.422281    11.00000    0.04783    0.04311 =
         0.02574   -0.00046    0.00150    0.00122
N1    3    0.192714   -0.163683    0.677980    11.00000    0.05802    0.02479 =
         0.04574   -0.00624    0.00813   -0.00990
AFIX   7
H1A   2    0.080170   -0.240030    0.625616    11.00000   -1.20000
H1B   2    0.281260   -0.303833    0.711025    11.00000   -1.20000
AFIX  66
C2    1    0.294263    0.390917    0.445426    11.00000    0.05393    0.02797 =
         0.03591    0.00202   -0.00453   -0.00406
AFIX  43
H2    2    0.220438    0.490032    0.374305    11.00000   -1.20000
AFIX  65
C3    1    0.191045    0.186576    0.508288    11.00000    0.04430    0.03332 =
         0.03591   -0.00721   -0.00333   -0.00407
AFIX  43
H3    2    0.048159    0.148972    0.479225    11.00000   -1.20000
AFIX  65
C4    1    0.301386    0.038438    0.614587    11.00000    0.03978    0.02357 =
         0.03514   -0.00598    0.00919   -0.00360
C5    1    0.514945    0.094641    0.658025    11.00000    0.04029    0.03066 =
         0.04212    0.00510   -0.00466   -0.00069
AFIX  43
H5    2    0.588770   -0.004474    0.729146    11.00000   -1.20000
AFIX  65
C6    1    0.618166    0.298981    0.595164    11.00000    0.04191    0.03623 =
         0.03626    0.00179   -0.00203   -0.00285
AFIX  43
H6    2    0.761052    0.336584    0.624228    11.00000   -1.20000
AFIX  65
C1    1    0.507828    0.447121    0.488865    11.00000    0.04897    0.02424 =
         0.02494   -0.00433    0.00410   -0.00507
AFIX   0
HKLF 4




REM  paba04 in Pn
REM R1 =  0.0410 for     396 Fo > 4sig(Fo)  and  0.0559 for all     471 data
REM     81 parameters refined using     71 restraints

END  
     
WGHT      0.0465      0.1521 

REM Highest difference peak  0.162,  deepest hole -0.163,  1-sigma level  0.042
Q1    1   0.4498 -0.1603  0.5228  11.00000  0.05    0.16
Q2    1   0.6905  1.0058  0.2662  11.00000  0.05    0.16
Q3    1   0.7057  0.6701  0.2479  11.00000  0.05    0.15
Q4    1  -0.1824  0.1633  0.4021  11.00000  0.05    0.13
Q5    1   0.7112  0.1731  0.8389  11.00000  0.05    0.13
Q6    1   0.3533 -0.3326  0.6052  11.00000  0.05    0.13
Q7    1   0.6552  0.8401  0.4992  11.00000  0.05    0.13
Q8    1   0.3430  0.6934  0.5012  11.00000  0.05    0.12
Q9    1   0.0007  0.4725  0.3408  11.00000  0.05    0.12
Q10   1   0.5876 -0.3449  0.6839  11.00000  0.05    0.12
Q11   1   0.1301  0.6549  0.4217  11.00000  0.05    0.12
Q12   1   0.1155  0.0415  0.4579  11.00000  0.05    0.12
Q13   1   0.7762  0.0044  0.5946  11.00000  0.05    0.12
Q14   1   0.5958  0.8426  0.1790  11.00000  0.05    0.11
Q15   1   0.6251  0.4699  0.3431  11.00000  0.05    0.11
Q16   1   0.5806  0.6608  0.6168  11.00000  0.05    0.11
Q17   1   0.0843 -0.4750  0.6727  11.00000  0.05    0.11
Q18   1   0.3912  0.3241  0.7148  11.00000  0.05    0.11
Q19   1   0.5635  0.0167  0.5696  11.00000  0.05    0.11
Q20   1   0.0274  0.1859  0.4005  11.00000  0.05    0.11

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0410 for 396 Fo > 4sig(Fo) and 0.0559 for all 1497 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.16, deepest hole -0.16
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0559
  REM R1_gt = 0.0410
  REM wR_ref = 0.1066
  REM GOOF = 1.108
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 1497
  REM Reflections_gt = 396
  REM Parameters = n/a
  REM Hole = -0.16
  REM Peak = 0.16
  REM Flack = 1.3(10)

  
;
_cod_data_source_file            c8ce01882k2.cif
_cod_data_source_block           paba04
_cod_depositor_comments
'Adding full bibliography for 7232195--7232199.cif.'
_cod_database_code               7232197
_shelx_shelxl_version_number     2016/6
_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   0.995
_shelx_estimated_absorpt_t_min   0.984
_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 O(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Rotating group:
 N1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
3.c Fitted hexagon refined as free rotating group:
 C2(C3,C4,C5,C6,C1)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, 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
O2 O 0.8145(13) 0.6985(13) 0.4510(7) 0.057(3) Uani 1 1 d . U
O1 O 0.5037(12) 0.7923(12) 0.3270(6) 0.047(3) Uani 1 1 d . U
H1 H 0.579130 0.884198 0.286719 0.071 Uiso 1 1 calc GR .
C7 C 0.623(2) 0.6516(19) 0.4223(10) 0.040(3) Uani 1 1 d . U
N1 N 0.1927(15) -0.1637(15) 0.6780(8) 0.043(3) Uani 1 1 d . U
H1A H 0.080170 -0.240030 0.625616 0.052 Uiso 1 1 d GR .
H1B H 0.281260 -0.303833 0.711025 0.052 Uiso 1 1 d GR .
C2 C 0.2943(10) 0.3909(11) 0.4454(5) 0.041(3) Uani 1 1 d . U
H2 H 0.220438 0.490032 0.374305 0.049 Uiso 1 1 calc R .
C3 C 0.1910(10) 0.1866(11) 0.5083(6) 0.039(3) Uani 1 1 d G U
H3 H 0.048159 0.148972 0.479225 0.047 Uiso 1 1 calc R .
C4 C 0.3014(11) 0.0384(11) 0.6146(6) 0.033(3) Uani 1 1 d G U
C5 C 0.5149(11) 0.0946(11) 0.6580(6) 0.039(3) Uani 1 1 d G U
H5 H 0.588770 -0.004474 0.729146 0.047 Uiso 1 1 calc R .
C6 C 0.6182(10) 0.2990(12) 0.5952(6) 0.039(4) Uani 1 1 d G U
H6 H 0.761052 0.336584 0.624228 0.047 Uiso 1 1 calc R .
C1 C 0.5078(10) 0.4471(12) 0.4889(6) 0.033(3) Uani 1 1 d G U
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.044(7) 0.055(5) 0.067(6) 0.014(3) 0.002(5) -0.005(3)
O1 0.046(7) 0.055(5) 0.037(5) 0.012(3) 0.000(5) -0.011(3)
C7 0.048(9) 0.043(7) 0.026(6) 0.000(4) 0.002(6) 0.001(5)
N1 0.058(10) 0.025(6) 0.046(6) -0.006(4) 0.008(5) -0.010(4)
C2 0.054(9) 0.028(6) 0.036(7) 0.002(5) -0.005(5) -0.004(5)
C3 0.044(10) 0.033(6) 0.036(5) -0.007(4) -0.003(5) -0.004(5)
C4 0.040(9) 0.024(5) 0.035(6) -0.006(4) 0.009(6) -0.004(4)
C5 0.040(9) 0.031(6) 0.042(7) 0.005(5) -0.005(5) -0.001(4)
C6 0.042(10) 0.036(6) 0.036(7) 0.002(5) -0.002(6) -0.003(5)
C1 0.049(8) 0.024(6) 0.025(6) -0.004(4) 0.004(5) -0.005(4)
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
C7 O1 H1 109.5
O2 C7 O1 121.0(11)
O2 C7 C1 124.7(7)
O1 C7 C1 114.2(11)
H1A N1 H1B 109.9
C4 N1 H1A 112.6
C4 N1 H1B 109.2
C3 C2 H2 120.0
C3 C2 C1 120.0
C1 C2 H2 120.0
C2 C3 H3 120.0
C4 C3 C2 120.0
C4 C3 H3 120.0
C3 C4 N1 119.0(5)
C3 C4 C5 120.0
C5 C4 N1 121.0(5)
C4 C5 H5 120.0
C6 C5 C4 120.0
C6 C5 H5 120.0
C5 C6 H6 120.0
C5 C6 C1 120.0
C1 C6 H6 120.0
C2 C1 C7 121.4(5)
C6 C1 C7 118.5(5)
C6 C1 C2 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C7 1.233(16)
O1 H1 0.8200
O1 C7 1.316(11)
C7 C1 1.457(15)
N1 H1A 0.8973
N1 H1B 0.8892
N1 C4 1.406(11)
C2 H2 0.9300
C2 C3 1.3900
C2 C1 1.3900
C3 H3 0.9300
C3 C4 1.3900
C4 C5 1.3900
C5 H5 0.9300
C5 C6 1.3900
C6 H6 0.9300
C6 C1 1.3900
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
O2 C7 C1 C2 -175.5(9)
O2 C7 C1 C6 2.1(15)
O1 C7 C1 C2 5.7(13)
O1 C7 C1 C6 -176.7(7)
N1 C4 C5 C6 -178.9(6)
C2 C3 C4 N1 178.9(6)
C2 C3 C4 C5 0.0
C3 C2 C1 C7 177.6(8)
C3 C2 C1 C6 0.0
C3 C4 C5 C6 0.0
C4 C5 C6 C1 0.0
C5 C6 C1 C7 -177.7(8)
C5 C6 C1 C2 0.0
C1 C2 C3 C4 0.0
