# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_paba03
_database_code_depnum_ccdc_archive 'CCDC 1876686'
_audit_update_record             
;
2018-11-01 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;
_audit_creation_date             2018-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        'p-aminobenzoic acid'
_chemical_formula_moiety         'C7 H7 N O2'
_chemical_formula_sum            'C7 H7 N O2'
_chemical_formula_weight         137.14
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   6.4341(11)
_cell_length_b                   4.6151(3)
_cell_length_c                   10.5313(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.730(10)
_cell_angle_gamma                90
_cell_volume                     307.25(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    550
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.049
_cell_measurement_theta_min      3.938
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.984
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             144
_exptl_crystal_preparation       ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          
'crystal was housed in a diamond anvil cell hence the low completeness.'
_diffrn_standards_number         0
_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_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_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)'
_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_coef       .
_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_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.082
_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
_refine_special_details          
'RIGU restraints were used on the molecule. Hydrogen atoms were placed on the parent atoms and set to ride.'
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
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)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
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_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
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_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
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 . . . . ?

_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)

  
;
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_paba_anneal_151018_0m
_database_code_depnum_ccdc_archive 'CCDC 1876690'
_audit_update_record             
;
2018-11-01 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;
_audit_creation_date             2018-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        'p-aminobenzoic acid'
_chemical_formula_moiety         'C7 H7 N O2'
_chemical_formula_sum            'C7 H7 N O2'
_chemical_formula_weight         137.14
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   6.4003(11)
_cell_length_b                   4.5981(4)
_cell_length_c                   10.4452(15)
_cell_angle_alpha                90
_cell_angle_beta                 100.748(14)
_cell_angle_gamma                90
_cell_volume                     302.00(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    746
_cell_measurement_temperature    295.01
_cell_measurement_theta_max      25.105
_cell_measurement_theta_min      3.470
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0951 before and 0.0476 after correction. The Ratio of minimum to maximum transmission is 0.7098. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             144
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Crystals loaded into a diamond anvil cell and 1.3 GPa pressure applied. Growth of new solid form (not present form) was observed after 8 hours. Annealling this solid reduced the pressure to 0.8 GPa and the delta form.'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.403
_diffrn_reflns_Laue_measured_fraction_max 0.403
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1317
_diffrn_reflns_point_group_measured_fraction_full 0.381
_diffrn_reflns_point_group_measured_fraction_max 0.381
_diffrn_reflns_theta_full        23.253
_diffrn_reflns_theta_max         23.253
_diffrn_reflns_theta_min         3.470
_diffrn_ambient_temperature      295.01
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.403
_diffrn_measured_fraction_theta_max 0.403
_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_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          'Sample housed in a Diamond anvil cell'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.359
_reflns_Friedel_fraction_max     0.359
_reflns_number_gt                300
_reflns_number_total             333
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_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)'
_refine_diff_density_max         0.091
_refine_diff_density_min         -0.073
_refine_diff_density_rms         0.020
_refine_ls_abs_structure_details 
;
 Flack x determined using 129 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         333
_refine_ls_number_restraints     71
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0276
_refine_ls_restrained_S_all      0.938
_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)+(0.0341P)²+0.0695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0644
_refine_special_details          
'RIGU restraints were used and AFIX66 was used for the ring system. hydrogens of the amine and acid were found from difference map and are riding on  the parent atoms.'
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O2 O 0.8190(15) 0.6975(11) 0.4521(10) 0.048(5) Uani 1 1 d . U . . .
O1 O 0.4994(14) 0.7990(11) 0.3257(8) 0.040(6) Uani 1 1 d . U . . .
H1 H 0.565053 0.925362 0.294392 0.060 Uiso 1 1 calc GR . . . .
C7 C 0.638(3) 0.6566(16) 0.4271(18) 0.027(5) Uani 1 1 d . U . . .
N1 N 0.1886(16) -0.1764(11) 0.6777(11) 0.030(7) Uani 1 1 d . U . . .
H1A H 0.221602 -0.358657 0.662403 0.036 Uiso 1 1 d GR . . . .
H1B H 0.220097 -0.143978 0.761877 0.036 Uiso 1 1 d GR . . . .
C2 C 0.2898(12) 0.3904(8) 0.4435(7) 0.030(5) Uani 1 1 d . U . . .
H2 H 0.215865 0.490882 0.371868 0.036 Uiso 1 1 calc R . . . .
C3 C 0.1856(12) 0.1846(8) 0.5062(7) 0.025(6) Uani 1 1 d G U . . .
H3 H 0.041873 0.147448 0.476508 0.030 Uiso 1 1 calc R . . . .
C4 C 0.2961(13) 0.0345(7) 0.6132(7) 0.021(6) Uani 1 1 d G U . . .
C5 C 0.5109(13) 0.0900(8) 0.6575(7) 0.027(6) Uani 1 1 d G U . . .
H5 H 0.584865 -0.010454 0.729127 0.032 Uiso 1 1 calc R . . . .
C6 C 0.6152(12) 0.2958(9) 0.5948(7) 0.032(6) Uani 1 1 d G U . . .
H6 H 0.758861 0.332976 0.624488 0.039 Uiso 1 1 calc R . . . .
C1 C 0.5046(12) 0.4460(8) 0.4878(7) 0.026(5) 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 0.025(12) 0.054(3) 0.066(12) 0.010(4) 0.009(10) -0.009(5)
O1 0.040(13) 0.042(3) 0.041(11) 0.015(4) 0.012(11) 0.005(5)
C7 0.026(13) 0.025(3) 0.031(11) -0.008(5) 0.004(10) -0.002(6)
N1 0.040(15) 0.030(3) 0.023(13) 0.002(4) 0.014(14) 0.005(4)
C2 0.030(12) 0.026(3) 0.033(12) -0.006(5) 0.003(11) -0.005(5)
C3 0.011(13) 0.036(3) 0.024(13) -0.007(5) -0.005(12) -0.007(5)
C4 0.024(12) 0.023(3) 0.015(12) -0.007(5) 0.002(11) -0.003(5)
C5 0.027(14) 0.037(3) 0.014(12) 0.000(5) -0.004(11) 0.000(5)
C6 0.034(13) 0.025(3) 0.036(13) 0.003(5) 0.003(11) 0.000(5)
C1 0.019(11) 0.021(3) 0.039(11) -0.002(5) 0.008(10) 0.001(4)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O2 C7 1.16(3) . ?
O1 H1 0.8200 . ?
O1 C7 1.41(3) . ?
C7 C1 1.505(8) . ?
N1 H1A 0.8859 . ?
N1 H1B 0.8771 . ?
N1 C4 1.429(6) . ?
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_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
C7 O1 H1 109.5 . . ?
O2 C7 O1 123.8(9) . . ?
O2 C7 C1 129.2(19) . . ?
O1 C7 C1 106.9(15) . . ?
H1A N1 H1B 108.9 . . ?
C4 N1 H1A 113.9 . . ?
C4 N1 H1B 108.5 . . ?
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 119.9(8) . . ?
C3 C4 C5 120.0 . . ?
C5 C4 N1 120.1(8) . . ?
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 125.4(10) . . ?
C6 C1 C7 114.6(10) . . ?
C6 C1 C2 120.0 . . ?

_iucr_refine_instructions_details 
;
TITL mo_paba_anneal_151018_0m_a.res in Pn
    mo_paba_anneal_151018_0m.res
    created by SHELXL-2016/6 at 14:52:24 on 01-Nov-2018
REM Old TITL mo_PABA_anneal_151018_0m in Pn
REM SHELXT solution in Pn
REM R1 0.130, Rweak 0.017, Alpha 0.024, Orientation as input
REM Flack x = -0.788 ( 1.695 ) from Parsons' quotients
REM Formula found by SHELXT: C7 N2 O
CELL 0.71073 6.4003 4.5981 10.4452 90 100.748 90
ZERR 2 0.0011 0.0004 0.0015 0 0.014 0
LATT -1
SYMM 0.5+X,-Y,0.5+Z
SFAC C H N O
UNIT 14 14 2 4
RIGU

L.S. 25
PLAN  10
SIZE 0.2 0.15 0.02
TEMP 21.88
BOND $H
list 4
fmap 2 53
acta
SHEL 10 0.9
OMIT -1 0 5
OMIT 1 -3 -7
OMIT -3 2 9
OMIT -1 -4 -4
REM <olex2.extras>
REM <HklSrc "%.\\mo_PABA_anneal_151018_0m.hkl">
REM </olex2.extras>

WGHT    0.034100    0.069500
FVAR       4.02917
O2    4    0.819049    0.697482    0.452056    11.00000    0.02470    0.05390 =
         0.06605    0.00952    0.00911   -0.00859
O1    4    0.499411    0.799023    0.325728    11.00000    0.03954    0.04160 =
         0.04090    0.01512    0.01241    0.00538
AFIX 147
H1    2    0.565053    0.925362    0.294392    11.00000   -1.50000
AFIX   0
C7    1    0.637509    0.656553    0.427121    11.00000    0.02610    0.02487 =
         0.03101   -0.00846    0.00446   -0.00234
N1    3    0.188627   -0.176443    0.677732    11.00000    0.04005    0.03047 =
         0.02328    0.00234    0.01450    0.00457
AFIX   7
H1A   2    0.221602   -0.358657    0.662403    11.00000   -1.20000
H1B   2    0.220097   -0.143978    0.761877    11.00000   -1.20000
AFIX  66
C2    1    0.289824    0.390399    0.443474    11.00000    0.02955    0.02630 =
         0.03266   -0.00573    0.00329   -0.00513
AFIX  43
H2    2    0.215865    0.490882    0.371868    11.00000   -1.20000
AFIX  65
C3    1    0.185580    0.184635    0.506168    11.00000    0.01104    0.03562 =
         0.02438   -0.00704   -0.00471   -0.00740
AFIX  43
H3    2    0.041873    0.147448    0.476508    11.00000   -1.20000
AFIX  65
C4    1    0.296121    0.034451    0.613191    11.00000    0.02406    0.02348 =
         0.01533   -0.00722    0.00218   -0.00305
C5    1    0.510907    0.090029    0.657521    11.00000    0.02675    0.03661 =
         0.01444    0.00007   -0.00380    0.00043
AFIX  43
H5    2    0.584865   -0.010454    0.729127    11.00000   -1.20000
AFIX  65
C6    1    0.615154    0.295792    0.594828    11.00000    0.03392    0.02536 =
         0.03617    0.00343    0.00312    0.00017
AFIX  43
H6    2    0.758861    0.332976    0.624488    11.00000   -1.20000
AFIX  65
C1    1    0.504616    0.445978    0.487805    11.00000    0.01906    0.02127 =
         0.03912   -0.00205    0.00769    0.00085
AFIX   0
HKLF 4




REM  mo_paba_anneal_151018_0m_a.res in Pn
REM R1 =  0.0276 for     300 Fo > 4sig(Fo)  and  0.0334 for all     333 data
REM     81 parameters refined using     71 restraints

END  
     
WGHT      0.0345      0.0691 

REM Highest difference peak  0.091,  deepest hole -0.073,  1-sigma level  0.020
Q1    1   0.8183  0.6766  0.2769  11.00000  0.05    0.09
Q2    1   0.1061 -0.3193  0.6815  11.00000  0.05    0.08
Q3    1  -0.1017 -0.1736  0.6218  11.00000  0.05    0.07
Q4    1   0.5817  0.8092  0.1973  11.00000  0.05    0.07
Q5    1   0.8192  0.2861  0.6423  11.00000  0.05    0.07
Q6    1   0.9220  0.3528  0.5979  11.00000  0.05    0.07
Q7    1   0.2984  0.0648  0.7779  11.00000  0.05    0.07
Q8    1   0.1884 -0.5809  0.6561  11.00000  0.05    0.07
Q9    1   0.3531 -0.1620  0.4657  11.00000  0.05    0.06
Q10   1   0.2583 -0.4269  0.7959  11.00000  0.05    0.06

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0276 for 300 Fo > 4sig(Fo) and 0.0334 for all 1623 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.09, deepest hole -0.07
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0334
  REM R1_gt = 0.0276
  REM wR_ref = 0.0644
  REM GOOF = 1.039
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 1623
  REM Reflections_gt = 300
  REM Parameters = n/a
  REM Hole = -0.07
  REM Peak = 0.09
  REM Flack = 1.5(10)

  
;
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_paba04
_database_code_depnum_ccdc_archive 'CCDC 1876687'
_audit_update_record             
;
2018-11-01 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;
_audit_creation_date             2018-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        'p-aminobenzoic acid'
_chemical_formula_moiety         'C7 H7 N O2'
_chemical_formula_sum            'C7 H7 N O2'
_chemical_formula_weight         137.14
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   6.4342(10)
_cell_length_b                   4.6146(4)
_cell_length_c                   10.5397(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.667(9)
_cell_angle_gamma                90
_cell_volume                     307.53(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    498
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.333
_cell_measurement_theta_min      3.934
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.984
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             144
_exptl_crystal_preparation       ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          
'The crystal was housed in a Diamond anvil cell hence the los completness of the dataset'
_diffrn_standards_number         0
_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_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_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    ?
_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_coef       .
_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_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.033
_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
_refine_special_details          
'RIGU restraints were used and  the hydrogen atoms were placed on the parent atoms and allowed to ride'
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
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)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
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_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
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_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
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 . . . . ?

_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)

  
;
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lvp_paba_h2o_100k_0m
_database_code_depnum_ccdc_archive 'CCDC 1876688'
_audit_update_record             
;
2018-11-01 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;
_audit_creation_date             2018-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        '4-aminobenzoic acid'
_chemical_formula_moiety         'C7 H7 N O2'
_chemical_formula_sum            'C7 H7 N O2'
_chemical_formula_weight         137.14
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   6.4551(5)
_cell_length_b                   4.6740(4)
_cell_length_c                   10.5470(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.754(3)
_cell_angle_gamma                90
_cell_volume                     312.63(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3293
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.25
_cell_measurement_theta_min      7.48
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.840
_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_absorpt_special_details   ?
_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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             144
_exptl_crystal_preparation       ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_temperature      99.82
_diffrn_detector_area_resol_mean ?
_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_source                   ?
_diffrn_standards_number         0
_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_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_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)'
_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_coef       .
_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_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.068
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
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)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
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_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
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_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

_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)

  
;
_olex2_exptl_crystal_mounting_method 'Kapton loop'
_olex2_submission_original_sample_id LVP_PABA_100K
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_delta_paba_ambient_2_0m
_database_code_depnum_ccdc_archive 'CCDC 1876689'
_audit_update_record             
;
2018-11-01 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;
_audit_creation_date             2018-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        '4-aminobenzoic acid'
_chemical_formula_moiety         'C7 H7 N O2'
_chemical_formula_sum            'C7 H7 N O2'
_chemical_formula_weight         137.14
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   6.5086(5)
_cell_length_b                   4.6661(4)
_cell_length_c                   10.7596(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.6850(10)
_cell_angle_gamma                90
_cell_volume                     321.10(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3483
_cell_measurement_temperature    295
_cell_measurement_theta_max      32.37
_cell_measurement_theta_min      3.40
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.979
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             144
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_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_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_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)'
_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_coef       .
_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_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.030
_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
_refine_special_details          'RIGU applied'
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
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)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
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_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
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_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

_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)

  
;
_olex2_exptl_crystal_mounting_method 'kapton micro-loop'
_olex2_submission_special_instructions 'No special instructions were received'
