#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:52:49 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223640 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/21/7232195.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_7232195
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
_atom_sites_solution_primary     dual
_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                 100.730(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4341(11)
_cell_length_b                   4.6151(3)
_cell_length_c                   10.5313(7)
_cell_measurement_reflns_used    550
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.049
_cell_measurement_theta_min      3.938
_cell_volume                     307.25(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)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_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 0.425
_diffrn_measured_fraction_theta_max 0.425
_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  0.0299
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.425
_diffrn_reflns_Laue_measured_fraction_max 0.425
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1365
_diffrn_reflns_point_group_measured_fraction_full 0.400
_diffrn_reflns_point_group_measured_fraction_max 0.400
_diffrn_reflns_theta_full        23.296
_diffrn_reflns_theta_max         23.296
_diffrn_reflns_theta_min         4.416
_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  0.6717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0921 before and 0.0409 after correction. The Ratio of minimum to maximum transmission is 0.9017. 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    1.482
_exptl_crystal_description       block
_exptl_crystal_F_000             144
_exptl_crystal_recrystallization_method
'Recrystallsed at 0.49 GPa from a supersaturated solution in ethanol and heat annealed into a pair of crystals'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.103
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 130 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         357
_refine_ls_number_restraints     71
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0339
_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)+(0.0223P)²+0.1837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0769
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.374
_reflns_Friedel_fraction_max     0.374
_reflns_number_gt                320
_reflns_number_total             357
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL paba03_a.res in Pn
    paba03.res
    created by SHELXL-2016/6 at 14:57:40 on 01-Nov-2018
REM Old TITL paba03_a.res in Pn
REM SHELXT solution in Pn
REM R1 0.088, Rweak 0.015, Alpha 0.026, Orientation as input
REM Flack x = -0.031 ( 1.681 ) from Parsons' quotients
REM Formula found by SHELXT: C6 N O3
REM acta 52
CELL 0.71073 6.4341 4.6151 10.5313 90 100.73 90
ZERR 2 0.0011 0.0003 0.0007 0 0.01 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 0.075
TEMP 23
BOND $H
list 4
MORE -1
CONF
fmap 2 53
acta
OMIT 0 -3 -5
OMIT 3 -3 -1
REM <olex2.extras>
REM <HklSrc "%.\\paba03.hkl">
REM </olex2.extras>

WGHT    0.022300    0.183700
FVAR       2.81495
O2    4    0.815165    0.693327    0.452517    11.00000    0.02300    0.05046 =
         0.06246    0.01439    0.00208    0.00450
O1    4    0.506258    0.794885    0.327016    11.00000    0.02645    0.05211 =
         0.03079    0.01602   -0.00019   -0.00415
AFIX 147
H1    2    0.582223    0.892169    0.289118    11.00000   -1.50000
AFIX   0
C7    1    0.620180    0.660923    0.420662    11.00000    0.02437    0.04159 =
         0.02722   -0.00248    0.00639    0.01208
N1    3    0.188981   -0.163852    0.679010    11.00000    0.07441    0.03216 =
         0.04521   -0.00391    0.03185   -0.01311
AFIX   7
H1A   2    0.075843   -0.239161    0.626802    11.00000   -1.20000
H1B   2    0.277266   -0.304701    0.711520    11.00000   -1.20000
AFIX  66
C2    1    0.293589    0.389880    0.444597    11.00000    0.04867    0.03513 =
         0.03298   -0.00423    0.01274   -0.00618
AFIX  43
H2    2    0.220367    0.489071    0.373205    11.00000   -1.20000
AFIX  65
C3    1    0.189436    0.186194    0.507210    11.00000    0.02698    0.03315 =
         0.02618   -0.01489   -0.00435   -0.01502
AFIX  43
H3    2    0.046528    0.149106    0.477711    11.00000   -1.20000
AFIX  65
C4    1    0.298876    0.037942    0.613914    11.00000    0.02357    0.03123 =
         0.02818   -0.00806    0.00901    0.00553
C5    1    0.512468    0.093373    0.658005    11.00000    0.02588    0.04194 =
         0.02748    0.00949    0.00206    0.00758
AFIX  43
H5    2    0.585689   -0.005818    0.729398    11.00000   -1.20000
AFIX  65
C6    1    0.616625    0.297057    0.595393    11.00000    0.03712    0.03453 =
         0.03567   -0.00709    0.00565   -0.01265
AFIX  43
H6    2    0.759533    0.334143    0.624893    11.00000   -1.20000
AFIX  65
C1    1    0.507188    0.445312    0.488689    11.00000    0.05070    0.02473 =
         0.02064   -0.00614    0.00540   -0.00588
AFIX   0
HKLF 4




REM  paba03_a.res in Pn
REM R1 =  0.0339 for     320 Fo > 4sig(Fo)  and  0.0419 for all     357 data
REM     81 parameters refined using     71 restraints

END  
     
WGHT      0.0187      0.1707 

REM Highest difference peak  0.106,  deepest hole -0.103,  1-sigma level  0.032
Q1    1   0.3960  0.6190  0.2792  11.00000  0.05    0.11
Q2    1   0.2117 -0.3733  0.6581  11.00000  0.05    0.11
Q3    1   0.7683  0.9409  0.2607  11.00000  0.05    0.10
Q4    1   0.5262  0.7816  0.1564  11.00000  0.05    0.10
Q5    1   0.3699 -0.4799  0.6561  11.00000  0.05    0.10
Q6    1   0.3574  0.0989  0.7746  11.00000  0.05    0.09
Q7    1  -0.0631  0.1203  0.3608  11.00000  0.05    0.09
Q8    1   0.9275  0.4932  0.3818  11.00000  0.05    0.09
Q9    1   0.9800  0.5464  0.4811  11.00000  0.05    0.09
Q10   1   0.7011  0.6191  0.2840  11.00000  0.05    0.09
Q11   1   0.3970  1.0395  0.3821  11.00000  0.05    0.09
Q12   1  -0.1046 -0.0248  0.6452  11.00000  0.05    0.09
Q13   1   0.6660  0.1145  0.7827  11.00000  0.05    0.09
Q14   1   0.4030  0.9989  0.2377  11.00000  0.05    0.09
Q15   1   0.1010  0.3535  0.3923  11.00000  0.05    0.09
Q16   1   0.4360 -0.5326  0.7642  11.00000  0.05    0.08
Q17   1   0.6367  0.8636  0.5089  11.00000  0.05    0.08
Q18   1   0.6950  0.1168  0.5830  11.00000  0.05    0.08
Q19   1   0.1383 -0.3570  0.5156  11.00000  0.05    0.08
Q20   1   0.6965 -0.1761  0.6085  11.00000  0.05    0.08

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0339 for 320 Fo > 4sig(Fo) and 0.0419 for all 1472 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.11, deepest hole -0.10
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0419
  REM R1_gt = 0.0339
  REM wR_ref = 0.0769
  REM GOOF = 1.174
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 1472
  REM Reflections_gt = 320
  REM Parameters = n/a
  REM Hole = -0.10
  REM Peak = 0.11
  REM Flack = -0.6(10)

  
;
_cod_data_source_file            c8ce01882k2.cif
_cod_data_source_block           paba03
_cod_depositor_comments
'Adding full bibliography for 7232195--7232199.cif.'
_cod_database_code               7232195
_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   0.992
_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 0.815(3) 0.693(2) 0.4525(12) 0.046(7) Uani 1 1 d . U
O1 O 0.506(2) 0.7949(14) 0.3270(6) 0.037(7) Uani 1 1 d . U
H1 H 0.582223 0.892169 0.289118 0.056 Uiso 1 1 calc GR .
C7 C 0.620(5) 0.661(3) 0.4207(18) 0.031(7) Uani 1 1 d . U
N1 N 0.189(3) -0.1639(15) 0.6790(10) 0.048(8) Uani 1 1 d . U
H1A H 0.075843 -0.239161 0.626802 0.058 Uiso 1 1 d GR .
H1B H 0.277266 -0.304701 0.711520 0.058 Uiso 1 1 d GR .
C2 C 0.2936(18) 0.3899(11) 0.4446(6) 0.038(6) Uani 1 1 d . U
H2 H 0.220367 0.489071 0.373205 0.046 Uiso 1 1 calc R .
C3 C 0.1894(18) 0.1862(11) 0.5072(7) 0.030(5) Uani 1 1 d G U
H3 H 0.046528 0.149106 0.477711 0.036 Uiso 1 1 calc R .
C4 C 0.2989(19) 0.0379(10) 0.6139(7) 0.027(5) Uani 1 1 d G U
C5 C 0.5125(19) 0.0934(11) 0.6580(7) 0.032(6) Uani 1 1 d G U
H5 H 0.585689 -0.005818 0.729398 0.039 Uiso 1 1 calc R .
C6 C 0.6166(18) 0.2971(13) 0.5954(7) 0.036(6) Uani 1 1 d G U
H6 H 0.759533 0.334143 0.624893 0.043 Uiso 1 1 calc R .
C1 C 0.5072(18) 0.4453(11) 0.4887(7) 0.032(6) 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 0.02(2) 0.050(4) 0.062(8) 0.014(5) 0.002(12) 0.005(8)
O1 0.03(2) 0.052(4) 0.031(5) 0.016(4) 0.000(10) -0.004(6)
C7 0.02(2) 0.042(6) 0.027(9) -0.002(6) 0.006(12) 0.012(10)
N1 0.07(2) 0.032(5) 0.045(8) -0.004(5) 0.032(13) -0.013(7)
C2 0.049(16) 0.035(5) 0.033(8) -0.004(5) 0.013(10) -0.006(9)
C3 0.027(16) 0.033(5) 0.026(6) -0.015(5) -0.004(9) -0.015(8)
C4 0.024(16) 0.031(5) 0.028(7) -0.008(5) 0.009(10) 0.006(7)
C5 0.026(17) 0.042(6) 0.027(8) 0.009(6) 0.002(10) 0.008(8)
C6 0.037(17) 0.035(5) 0.036(7) -0.007(6) 0.006(10) -0.013(8)
C1 0.051(17) 0.025(4) 0.021(6) -0.006(5) 0.005(9) -0.006(6)
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 123.8(14)
O2 C7 C1 120(2)
O1 C7 C1 116(3)
H1A N1 H1B 109.9
C4 N1 H1A 112.2
C4 N1 H1B 109.0
C3 C2 H2 120.0
C3 C2 C1 120.0
C1 C2 H2 120.0
C2 C3 H3 120.0
C2 C3 C4 120.0
C4 C3 H3 120.0
C3 C4 N1 119.3(10)
C5 C4 N1 120.6(10)
C5 C4 C3 120.0
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 120.1(14)
C6 C1 C7 119.8(14)
C6 C1 C2 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C7 1.25(4)
O1 H1 0.8200
O1 C7 1.27(3)
C7 C1 1.492(17)
N1 H1A 0.8966
N1 H1B 0.8888
N1 C4 1.420(10)
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 -173.7(11)
O2 C7 C1 C6 5.5(16)
O1 C7 C1 C2 3.4(12)
O1 C7 C1 C6 -177.4(7)
N1 C4 C5 C6 -178.3(5)
C2 C3 C4 N1 178.3(5)
C2 C3 C4 C5 0.0
C3 C2 C1 C7 179.2(7)
C3 C2 C1 C6 0.0
C3 C4 C5 C6 0.0
C4 C5 C6 C1 0.0
C5 C6 C1 C7 -179.2(6)
C5 C6 C1 C2 0.0
C1 C2 C3 C4 0.0
