#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:52:49 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223640 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/21/7232199.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_7232199
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        '4-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                 100.6850(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5086(5)
_cell_length_b                   4.6661(4)
_cell_length_c                   10.7596(8)
_cell_measurement_reflns_used    3483
_cell_measurement_temperature    295
_cell_measurement_theta_max      32.37
_cell_measurement_theta_min      3.40
_cell_volume                     321.10(4)
_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      295.03
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0399
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7461
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.584
_diffrn_reflns_theta_min         3.403
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1202 before and 0.0619 after correction. The Ratio of minimum to maximum transmission is 0.8072. 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    1.418
_exptl_crystal_description       plate
_exptl_crystal_F_000             144
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 955 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         2326
_refine_ls_number_restraints     71
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0408
_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)+(0.0644P)²+0.0283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2079
_reflns_number_total             2326
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL mo_delta_paba_ambient_2_0m_a.res in Pn
    mo_delta_paba_ambient_2_0m.res
    created by SHELXL-2016/6 at 14:40:27 on 01-Nov-2018
REM Old TITL mo_delta_PABA_ambient_2_0m in Pn
REM SHELXT solution in Pn
REM R1 0.101, Rweak 0.007, Alpha 0.001, Orientation as input
REM Flack x = -0.009 ( 0.590 ) from Parsons' quotients
REM Formula found by SHELXT: C8 O2
CELL 0.71073 6.5086 4.6661 10.7596 90 100.685 90
ZERR 2 0.0005 0.0004 0.0008 0 0.001 0
LATT -1
SYMM 0.5+X,-Y,0.5+Z
SFAC C H N O
UNIT 14 14 2 4
EQIV $1 0.5+X,1-Y,-0.5+Z
RIGU

L.S. 25
PLAN  10
SIZE 0.2 0.15 0.02
TEMP 21.88
HTAB O1 N1_$1
BOND $H
list 4
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\mo_delta_PABA_ambient_2_0m.hkl">
REM </olex2.extras>

WGHT    0.064400    0.028300
FVAR       1.77203
O2    4    0.810041    0.705335    0.454685    11.00000    0.02711    0.05767 =
         0.06351    0.01586    0.00288   -0.00988
O1    4    0.507290    0.782469    0.324247    11.00000    0.03442    0.05270 =
         0.03636    0.01403    0.00132   -0.01070
AFIX 147
H1    2    0.580071    0.888823    0.289875    11.00000   -1.50000
AFIX   0
C7    1    0.624741    0.656680    0.422741    11.00000    0.02758    0.02962 =
         0.03047   -0.00126    0.00714   -0.00278
N1    3    0.190870   -0.147097    0.675911    11.00000    0.04550    0.03267 =
         0.03968   -0.00216    0.01630   -0.00753
AFIX   7
H1A   2    0.272430   -0.287076    0.705162    11.00000   -1.20000
H1B   2    0.093071   -0.246019    0.631041    11.00000   -1.20000
AFIX   0
C1    1    0.508004    0.449285    0.487352    11.00000    0.02301    0.02790 =
         0.02798   -0.00233    0.00324   -0.00239
C4    1    0.299830    0.047485    0.611398    11.00000    0.03606    0.02710 =
         0.02873   -0.00488    0.01229   -0.00340
C6    1    0.612407    0.306421    0.594335    11.00000    0.02617    0.03986 =
         0.03345    0.00457    0.00056   -0.00314
AFIX  43
H6    2    0.753160    0.344350    0.624271    11.00000   -1.20000
AFIX   0
C2    1    0.296704    0.393410    0.444511    11.00000    0.02652    0.03617 =
         0.02892    0.00124    0.00146   -0.00457
AFIX  43
H2    2    0.224767    0.490616    0.374271    11.00000   -1.20000
AFIX   0
C5    1    0.510125    0.110105    0.656246    11.00000    0.03558    0.03834 =
         0.03288    0.00695    0.00270   -0.00052
AFIX  43
H5    2    0.581400    0.018690    0.728305    11.00000   -1.20000
AFIX   0
C3    1    0.192065    0.193356    0.505843    11.00000    0.02608    0.03833 =
         0.03486   -0.00314    0.00462   -0.00757
AFIX  43
H3    2    0.050883    0.156972    0.476624    11.00000   -1.20000
AFIX   0
HKLF 4




REM  mo_delta_paba_ambient_2_0m_a.res in Pn
REM R1 =  0.0408 for    2079 Fo > 4sig(Fo)  and  0.0458 for all    2326 data
REM     93 parameters refined using     71 restraints

END  
     
WGHT      0.0644      0.0283 

REM Highest difference peak  0.267,  deepest hole -0.192,  1-sigma level  0.047
Q1    1   0.5651  0.5503  0.4550  11.00000  0.05    0.27
Q2    1   0.5623  0.3760  0.5354  11.00000  0.05    0.25
Q3    1   0.2465  0.3002  0.4824  11.00000  0.05    0.24
Q4    1   0.2474  0.1382  0.5651  11.00000  0.05    0.22
Q5    1   0.4027  0.0664  0.6387  11.00000  0.05    0.21
Q6    1   0.4124  0.4007  0.4592  11.00000  0.05    0.21
Q7    1   0.5543  0.2058  0.6195  11.00000  0.05    0.20
Q8    1   0.7732  0.6356  0.4061  11.00000  0.05    0.17
Q9    1   0.2444 -0.0520  0.6377  11.00000  0.05    0.16
Q10   1   0.5752  0.6745  0.3184  11.00000  0.05    0.14

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0408 for 2079 Fo > 4sig(Fo) and 0.0458 for all 7940 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.27, deepest hole -0.19
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0458
  REM R1_gt = 0.0408
  REM wR_ref = 0.1154
  REM GOOF = 1.046
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 7940
  REM Reflections_gt = 2079
  REM Parameters = n/a
  REM Hole = -0.19
  REM Peak = 0.27
  REM Flack = -0.4(6)

  
;
_cod_data_source_file            c8ce01882k2.cif
_cod_data_source_block           mo_delta_paba_ambient_2_0m
_cod_depositor_comments
'Adding full bibliography for 7232195--7232199.cif.'
_cod_database_code               7232199
_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   0.998
_shelx_estimated_absorpt_t_min   0.979
_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:
 C6(H6), C2(H2), C5(H5), C3(H3)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_exptl_crystal_mounting_method 'kapton micro-loop'
_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 0.8100(2) 0.7053(4) 0.45469(18) 0.0501(4) Uani 1 1 d . U
O1 O 0.5073(2) 0.7825(4) 0.32425(15) 0.0418(4) Uani 1 1 d . U
H1 H 0.580071 0.888823 0.289875 0.063 Uiso 1 1 calc GR .
C7 C 0.6247(3) 0.6567(4) 0.42274(16) 0.0290(3) Uani 1 1 d . U
N1 N 0.1909(3) -0.1471(4) 0.67591(17) 0.0382(4) Uani 1 1 d . U
H1A H 0.272430 -0.287076 0.705162 0.046 Uiso 1 1 d GR .
H1B H 0.093071 -0.246019 0.631041 0.046 Uiso 1 1 d GR .
C1 C 0.5080(2) 0.4493(4) 0.48735(15) 0.0265(3) Uani 1 1 d . U
C4 C 0.2998(3) 0.0475(4) 0.61140(16) 0.0298(4) Uani 1 1 d . U
C6 C 0.6124(3) 0.3064(5) 0.59433(18) 0.0338(4) Uani 1 1 d . U
H6 H 0.753160 0.344350 0.624271 0.041 Uiso 1 1 calc R .
C2 C 0.2967(3) 0.3934(4) 0.44451(16) 0.0310(4) Uani 1 1 d . U
H2 H 0.224767 0.490616 0.374271 0.037 Uiso 1 1 calc R .
C5 C 0.5101(3) 0.1101(5) 0.65625(18) 0.0361(4) Uani 1 1 d . U
H5 H 0.581400 0.018690 0.728305 0.043 Uiso 1 1 calc R .
C3 C 0.1921(3) 0.1934(4) 0.50584(17) 0.0332(4) Uani 1 1 d . U
H3 H 0.050883 0.156972 0.476624 0.040 Uiso 1 1 calc R .
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 0.0271(6) 0.0577(10) 0.0635(10) 0.0159(8) 0.0029(6) -0.0099(7)
O1 0.0344(6) 0.0527(8) 0.0364(6) 0.0140(6) 0.0013(5) -0.0107(6)
C7 0.0276(7) 0.0296(8) 0.0305(7) -0.0013(6) 0.0071(6) -0.0028(6)
N1 0.0455(9) 0.0327(9) 0.0397(9) -0.0022(6) 0.0163(7) -0.0075(7)
C1 0.0230(7) 0.0279(8) 0.0280(7) -0.0023(6) 0.0032(5) -0.0024(6)
C4 0.0361(9) 0.0271(8) 0.0287(8) -0.0049(6) 0.0123(6) -0.0034(7)
C6 0.0262(8) 0.0399(10) 0.0334(8) 0.0046(7) 0.0006(6) -0.0031(7)
C2 0.0265(7) 0.0362(9) 0.0289(7) 0.0012(7) 0.0015(6) -0.0046(6)
C5 0.0356(9) 0.0383(9) 0.0329(8) 0.0069(7) 0.0027(7) -0.0005(7)
C3 0.0261(7) 0.0383(9) 0.0349(8) -0.0031(7) 0.0046(6) -0.0076(7)
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 122.71(18)
O2 C7 C1 124.00(17)
O1 C7 C1 113.28(15)
H1A N1 H1B 98.0
C4 N1 H1A 109.6
C4 N1 H1B 117.2
C6 C1 C7 119.11(15)
C2 C1 C7 121.90(15)
C2 C1 C6 118.99(16)
C5 C4 N1 120.99(18)
C5 C4 C3 119.46(16)
C3 C4 N1 119.42(18)
C1 C6 H6 119.6
C5 C6 C1 120.88(17)
C5 C6 H6 119.6
C1 C2 H2 119.7
C1 C2 C3 120.59(16)
C3 C2 H2 119.7
C4 C5 H5 119.9
C6 C5 C4 120.27(17)
C6 C5 H5 119.9
C4 C3 H3 120.1
C2 C3 C4 119.76(15)
C2 C3 H3 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C7 1.213(2)
O1 H1 0.8200
O1 C7 1.323(2)
C7 C1 1.481(2)
N1 H1A 0.8634
N1 H1B 0.8587
N1 C4 1.411(3)
C1 C6 1.393(2)
C1 C2 1.392(2)
C4 C5 1.395(3)
C4 C3 1.396(3)
C6 H6 0.9300
C6 C5 1.375(3)
C2 H2 0.9300
C2 C3 1.392(3)
C5 H5 0.9300
C3 H3 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.82 1.95 2.753(2) 165.8 2_564
