#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:52:49 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223640 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/21/7232198.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_7232198
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             2018-10-23
_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                 100.754(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4551(5)
_cell_length_b                   4.6740(4)
_cell_length_c                   10.5470(9)
_cell_measurement_reflns_used    3293
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.25
_cell_measurement_theta_min      7.48
_cell_volume                     312.63(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      99.82
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3384
_diffrn_reflns_point_group_measured_fraction_full 0.811
_diffrn_reflns_point_group_measured_fraction_max 0.798
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.243
_diffrn_reflns_theta_min         7.478
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.905
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0715 before and 0.0460 after correction. The Ratio of minimum to maximum transmission is 0.8525. The λ/2 correction factor is Not present.'
_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    1.457
_exptl_crystal_description       plate
_exptl_crystal_F_000             144
_exptl_crystal_recrystallization_method
'crystals obtained from high pressure experiment in large volume press.  Saturated solution used as the PTM.  PABA alpha form was used for compression'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 350 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1014
_refine_ls_number_restraints     71
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0287
_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)+(0.0412P)²+0.0455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0730
_reflns_Friedel_coverage         0.594
_reflns_Friedel_fraction_full    0.623
_reflns_Friedel_fraction_max     0.597
_reflns_number_gt                991
_reflns_number_total             1014
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;

    lvp_paba_h2o_100k_0m.res created by SHELXL-2014/7

TITL lvp_paba_h2o_100k_0m_a.res in Pn
REM Old TITL LVP_PABA_H2O_100K_0m in Pn
REM SHELXT solution in Pn
REM R1 0.065, Rweak 0.006, Alpha 0.002, Orientation as input
REM Flack x = 0.030 ( 0.107 ) from Parsons' quotients
REM Formula found by SHELXT: C7 N O2
CELL 1.54178 6.4551 4.674 10.547 90 100.754 90
ZERR 2 0.0005 0.0004 0.0009 0 0.003 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. 50
PLAN  5
SIZE 0.2 0.18 0.02
TEMP -173.33
HTAB O2 N1_$1
BOND $H
list 4
fmap 2 53
acta
OMIT -4 1 6
OMIT -1 4 5
OMIT -3 4 2
OMIT 2 2 3
REM <olex2.extras>
REM <HklSrc "%.\\LVP_PABA_H2O_100K_0m.hkl">
REM </olex2.extras>
 
WGHT    0.041200    0.045500
FVAR       1.71898
O2    4    0.501572    0.199752    0.325882    11.00000    0.01478    0.01978 =
         0.01478   -0.00500    0.00028    0.00327
AFIX 147
H2    2    0.575562    0.084594    0.292386    11.00000   -1.50000
AFIX   0
O1    4    0.812051    0.294830    0.453279    11.00000    0.01359    0.02251 =
         0.02319   -0.00405    0.00207    0.00224
N1    3    0.187811    1.156605    0.674772    11.00000    0.01934    0.01403 =
         0.01674   -0.00008    0.00522    0.00200
C4    1    0.296637    0.957416    0.610466    11.00000    0.01791    0.01208 =
         0.01273    0.00259    0.00521    0.00014
C7    1    0.622537    0.336875    0.422609    11.00000    0.01464    0.01272 =
         0.01287    0.00126    0.00193   -0.00112
C6    1    0.613037    0.697273    0.593991    11.00000    0.01311    0.01553 =
         0.01500    0.00160    0.00090    0.00037
AFIX  43
H6    2    0.758550    0.660318    0.624382    11.00000   -1.20000
AFIX   0
C1    1    0.505009    0.547663    0.487276    11.00000    0.01380    0.01288 =
         0.01253    0.00208    0.00251    0.00030
C3    1    0.186544    0.804153    0.504992    11.00000    0.01284    0.01624 =
         0.01513    0.00224    0.00210    0.00157
AFIX  43
H3    2    0.040714    0.839588    0.475002    11.00000   -1.20000
AFIX   0
C5    1    0.510309    0.899063    0.656048    11.00000    0.01776    0.01613 =
         0.01369   -0.00079    0.00197   -0.00121
AFIX  43
H5    2    0.584700    0.997637    0.729383    11.00000   -1.20000
AFIX   0
C2    1    0.290411    0.600449    0.444233    11.00000    0.01624    0.01503 =
         0.01273    0.00010    0.00056   -0.00043
AFIX  43
H2A   2    0.215074    0.496293    0.372935    11.00000   -1.20000
AFIX   0
H1A   2    0.266760    1.288323    0.707242    11.00000    0.01686
H1B   2    0.070503    1.246468    0.613710    11.00000    0.03006
HKLF 4
 
REM  lvp_paba_h2o_100k_0m_a.res in Pn
REM R1 =  0.0287 for     991 Fo > 4sig(Fo)  and  0.0297 for all    1014 data
REM    100 parameters refined using     71 restraints
 
END  
     
WGHT      0.0411      0.0455 

REM Highest difference peak  0.178,  deepest hole -0.239,  1-sigma level  0.055
Q1    1   0.9005  0.2841  0.3398  11.00000  0.05    0.18
Q2    1   0.5597  0.4415  0.4569  11.00000  0.05    0.16
Q3    1   0.8662  0.4117  0.5955  11.00000  0.05    0.16
Q4    1   0.8490  0.1421  0.5751  11.00000  0.05    0.16
Q5    1   0.5403  0.3613  0.1871  11.00000  0.05    0.16

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0287 for 991 Fo > 4sig(Fo) and 0.0297 for all 3646 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.18, deepest hole -0.24
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0297
  REM R1_gt = 0.0287
  REM wR_ref = 0.0730
  REM GOOF = 1.106
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 3646
  REM Reflections_gt = 991
  REM Parameters = n/a
  REM Hole = -0.24
  REM Peak = 0.18
  REM Flack = 0.01(12)

  
;
_cod_data_source_file            c8ce01882k2.cif
_cod_data_source_block           lvp_paba_h2o_100k_0m
_cod_depositor_comments
'Adding full bibliography for 7232195--7232199.cif.'
_cod_database_code               7232198
_shelx_shelxl_version_number     2014/7
_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   0.982
_shelx_estimated_absorpt_t_min   0.840
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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 Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C2(H2A)
3.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_exptl_crystal_mounting_method 'Kapton loop'
_olex2_submission_original_sample_id LVP_PABA_100K
_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 0.5016(2) 0.1998(3) 0.32588(14) 0.0168(3) Uani 1 1 d . U
H2 H 0.5756 0.0846 0.2924 0.025 Uiso 1 1 calc GR .
O1 O 0.8121(2) 0.2948(3) 0.45328(15) 0.0199(3) Uani 1 1 d . U
N1 N 0.1878(3) 1.1566(4) 0.67477(17) 0.0165(4) Uani 1 1 d . U
C4 C 0.2966(3) 0.9574(4) 0.61047(18) 0.0139(4) Uani 1 1 d . U
C7 C 0.6225(3) 0.3369(4) 0.42261(18) 0.0135(4) Uani 1 1 d . U
C6 C 0.6130(3) 0.6973(4) 0.59399(19) 0.0148(4) Uani 1 1 d . U
H6 H 0.7585 0.6603 0.6244 0.018 Uiso 1 1 calc R .
C1 C 0.5050(3) 0.5477(4) 0.48728(18) 0.0131(4) Uani 1 1 d . U
C3 C 0.1865(3) 0.8042(4) 0.50499(17) 0.0148(4) Uani 1 1 d . U
H3 H 0.0407 0.8396 0.4750 0.018 Uiso 1 1 calc R .
C5 C 0.5103(3) 0.8991(4) 0.65605(18) 0.0160(4) Uani 1 1 d . U
H5 H 0.5847 0.9976 0.7294 0.019 Uiso 1 1 calc R .
C2 C 0.2904(3) 0.6004(4) 0.44423(18) 0.0149(4) Uani 1 1 d . U
H2A H 0.2151 0.4963 0.3729 0.018 Uiso 1 1 calc R .
H1A H 0.267(4) 1.288(5) 0.707(3) 0.017(6) Uiso 1 1 d . .
H1B H 0.071(5) 1.246(6) 0.614(3) 0.030(8) Uiso 1 1 d . .
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 0.0148(6) 0.0198(7) 0.0148(7) -0.0050(6) 0.0003(5) 0.0033(5)
O1 0.0136(6) 0.0225(7) 0.0232(8) -0.0040(6) 0.0021(5) 0.0022(5)
N1 0.0193(9) 0.0140(9) 0.0167(8) -0.0001(7) 0.0052(7) 0.0020(7)
C4 0.0179(9) 0.0121(9) 0.0127(9) 0.0026(7) 0.0052(7) 0.0001(7)
C7 0.0146(9) 0.0127(9) 0.0129(9) 0.0013(7) 0.0019(7) -0.0011(7)
C6 0.0131(9) 0.0155(9) 0.0150(9) 0.0016(7) 0.0009(7) 0.0004(7)
C1 0.0138(9) 0.0129(9) 0.0125(9) 0.0021(6) 0.0025(7) 0.0003(6)
C3 0.0128(9) 0.0162(9) 0.0151(9) 0.0022(7) 0.0021(7) 0.0016(7)
C5 0.0178(9) 0.0161(9) 0.0137(9) -0.0008(7) 0.0020(7) -0.0012(7)
C2 0.0162(9) 0.0150(9) 0.0127(9) 0.0001(7) 0.0006(7) -0.0004(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 O2 H2 109.5
C4 N1 H1A 111.4(18)
C4 N1 H1B 110.8(17)
H1A N1 H1B 107(2)
C3 C4 N1 119.61(18)
C5 C4 N1 120.63(17)
C5 C4 C3 119.64(17)
O2 C7 C1 113.30(16)
O1 C7 O2 122.82(19)
O1 C7 C1 123.88(17)
C1 C6 H6 119.6
C5 C6 H6 119.6
C5 C6 C1 120.71(19)
C6 C1 C7 118.78(17)
C6 C1 C2 119.30(18)
C2 C1 C7 121.91(16)
C4 C3 H3 120.0
C2 C3 C4 120.03(17)
C2 C3 H3 120.0
C4 C5 H5 120.1
C6 C5 C4 119.87(18)
C6 C5 H5 120.1
C1 C2 H2A 119.8
C3 C2 C1 120.41(17)
C3 C2 H2A 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 H2 0.8400
O2 C7 1.328(2)
O1 C7 1.222(2)
N1 C4 1.414(3)
N1 H1A 0.83(3)
N1 H1B 0.99(3)
C4 C3 1.400(3)
C4 C5 1.400(3)
C7 C1 1.485(3)
C6 H6 0.9500
C6 C1 1.396(3)
C6 C5 1.386(3)
C1 C2 1.397(2)
C3 H3 0.9500
C3 C2 1.388(3)
C5 H5 0.9500
C2 H2A 0.9500
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
O2 H2 N1 0.84 1.92 2.734(2) 164.3 2_564
