# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_exp_169
_database_code_depnum_ccdc_archive 'CCDC 2009891'
loop_
_audit_author_name
_audit_author_address
'Sarah Wright'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2018-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        '4-amino-3-hydroxybenzoic acid'
_chemical_formula_moiety         'C7 H7 N O3'
_chemical_formula_sum            'C7 H7 N O3'
_chemical_formula_weight         153.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C7 O3 N1 H7'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.6926(9)
_cell_length_b                   8.1121(7)
_cell_length_c                   14.1796(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1344.95(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2016
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.9710
_cell_measurement_theta_min      4.1590
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.14646
_exptl_crystal_size_mid          0.06004
_exptl_crystal_size_min          0.00879
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6923
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.579
_diffrn_reflns_theta_min         3.360
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1636
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00 -32.00   1.00    3.62    --   10.40 178.00-120.00   44
  2  ω    -59.00   4.00   1.00    3.62    --   10.40 -37.00 120.00   63
  3  ω     54.00  94.00   1.00    3.62    --   10.40-178.00  30.00   40
  4  ω    -85.00 -38.00   1.00    3.62    --  -11.10-178.00 -60.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0172542000
_diffrn_orient_matrix_UB_12      0.0501150000
_diffrn_orient_matrix_UB_13      -0.0385538000
_diffrn_orient_matrix_UB_21      0.0208322000
_diffrn_orient_matrix_UB_22      -0.0707093000
_diffrn_orient_matrix_UB_23      -0.0237729000
_diffrn_orient_matrix_UB_31      -0.0542877000
_diffrn_orient_matrix_UB_32      -0.0113675000
_diffrn_orient_matrix_UB_33      -0.0212846000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1150
_reflns_number_total             1669
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1669
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      0.928
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1562
_refine_special_details          ?
_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.a Rotating group:
 N1(H1a,H1b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C3(H3a)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O3 O 0.07581(10) -0.01042(16) 0.67587(8) 0.0281(4) Uani 1 1 d . . . . .
H3 H 0.129234 -0.054525 0.645332 0.042 Uiso 1 1 calc GR . . . .
C2 C -0.14632(15) -0.1970(2) 0.52569(11) 0.0216(4) Uani 1 1 d . . . . .
C6 C -0.03767(15) -0.1600(2) 0.56074(11) 0.0221(4) Uani 1 1 d . . . . .
H6 H 0.028449 -0.204216 0.531118 0.026 Uiso 1 1 calc R . . . .
N1 N -0.10825(14) 0.09403(19) 0.76824(9) 0.0259(4) Uani 1 1 d . . . . .
H1A H -0.047390 0.154178 0.763206 0.031 Uiso 1 1 d GR . . . .
H1B H -0.166500 0.157803 0.777694 0.031 Uiso 1 1 d GR . . . .
C1 C -0.12385(16) 0.0020(2) 0.68448(11) 0.0211(4) Uani 1 1 d . . . . .
O1 O -0.06752(11) -0.38000(19) 0.41395(9) 0.0321(4) Uani 1 1 d . . . . .
H1 H -0.084089 -0.449531 0.372231 0.048 Uiso 1 1 calc GR . . . .
C7 C -0.16065(16) -0.3029(2) 0.44087(12) 0.0238(4) Uani 1 1 d . . . . .
C5 C -0.02666(14) -0.0586(2) 0.63897(12) 0.0209(4) Uani 1 1 d . . . . .
O2 O -0.25261(11) -0.31651(16) 0.40045(9) 0.0311(4) Uani 1 1 d . . . . .
C4 C -0.23136(15) -0.0355(2) 0.64957(12) 0.0249(4) Uani 1 1 d . . . . .
H4 H -0.297621 0.005840 0.680299 0.030 Uiso 1 1 calc R . . . .
C3 C -0.24250(15) -0.1332(2) 0.56976(12) 0.0255(4) Uani 1 1 d . . . . .
H3A H -0.316354 -0.156583 0.545228 0.031 Uiso 1 1 calc R . . . .


_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
O3 C5 1.365(2) . ?
C2 C6 1.397(2) . ?
C2 C7 1.488(2) . ?
C2 C3 1.387(2) . ?
C6 C5 1.387(2) . ?
N1 C1 1.415(2) . ?
C1 C5 1.396(2) . ?
C1 C4 1.385(2) . ?
O1 C7 1.312(2) . ?
C7 O2 1.223(2) . ?
C4 C3 1.388(3) . ?

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
C6 C2 C7 120.94(16) . . ?
C3 C2 C6 119.81(16) . . ?
C3 C2 C7 119.24(15) . . ?
C5 C6 C2 119.76(16) . . ?
C5 C1 N1 117.96(16) . . ?
C4 C1 N1 122.21(16) . . ?
C4 C1 C5 119.76(16) . . ?
O1 C7 C2 114.64(15) . . ?
O2 C7 C2 121.99(16) . . ?
O2 C7 O1 123.38(16) . . ?
O3 C5 C6 123.91(15) . . ?
O3 C5 C1 115.89(15) . . ?
C6 C5 C1 120.19(16) . . ?
C1 C4 C3 120.14(16) . . ?
C2 C3 C4 120.29(16) . . ?

_olex2_date_sample_data_collection 2018-11-14
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.228
_oxdiff_exptl_absorpt_empirical_full_min 0.878
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# 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_oacc34
_database_code_depnum_ccdc_archive 'CCDC 2009896'
loop_
_audit_author_name
_audit_author_address
'Sarah Wright'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2018-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        '4-amino-5-chloro-2-ethoxybenzoic acid'
_chemical_formula_moiety         'C9 H10 Cl N O3'
_chemical_formula_sum            'C9 H10 Cl N O3'
_chemical_formula_weight         215.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 O3 N1 Cl1 H10'
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'
Cl Cl 0.1484 0.1585 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7014(12)
_cell_length_b                   14.9141(12)
_cell_length_c                   6.9582(9)
_cell_angle_alpha                90
_cell_angle_beta                 109.984(14)
_cell_angle_gamma                90
_cell_volume                     946.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1247
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.2160
_cell_measurement_theta_min      4.1360
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.867
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 19 0 0.1262
13 2 0 0.2096
-5 -19 0 0.1262
0 16 -6 0.2369
1 7 -9 0.3110
-1 -7 9 0.3110
-13 -2 0 0.2096
1 21 0 0.0772
-1 -21 0 0.0772
0 -16 6 0.2369

_exptl_crystal_size_max          0.38246
_exptl_crystal_size_mid          0.2193
_exptl_crystal_size_min          0.08387
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.9994 19.0013 0.0001 0.2414 0.9527 0.0304
13.0003 2.0014 0.0007 -0.5589 0.6609 -0.5317
-4.9994 -19.0013 -0.0001 -0.2414 -0.9527 -0.0304
-0.0001 16.0001 -6.0006 0.1672 0.5629 0.8116
1.0005 6.9995 -9.0006 -0.2216 0.2379 0.9555
-1.0005 -6.9995 9.0006 0.2216 -0.2379 -0.9555
-13.0003 -2.0014 -0.0007 0.5589 -0.6609 0.5317
0.9993 21.0010 -0.0002 0.4789 0.8496 0.2277
-0.9993 -21.0010 0.0002 -0.4789 -0.8496 -0.2277
0.0001 -16.0001 6.0006 -0.1672 -0.5629 -0.8116

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0874
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4839
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.529
_diffrn_reflns_theta_min         3.402
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1636
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  78.00   1.00    1.35    --   10.40  57.00   0.00   88
  2  ω    -59.00  30.00   1.00    1.35    --   10.40 -57.00-150.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0468488000
_diffrn_orient_matrix_UB_12      0.0250326000
_diffrn_orient_matrix_UB_13      0.0388802000
_diffrn_orient_matrix_UB_21      0.0449395000
_diffrn_orient_matrix_UB_22      0.0383168000
_diffrn_orient_matrix_UB_23      0.0083607000
_diffrn_orient_matrix_UB_31      -0.0428801000
_diffrn_orient_matrix_UB_32      0.0128830000
_diffrn_orient_matrix_UB_33      -0.1009069000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1420
_reflns_number_total             2250
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0634
_refine_ls_restrained_S_all      0.958
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1900
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Rotating group:
 N1(H1A,H1B)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Me refined with riding coordinates:
 C9(H9A,H9B,H9C)
2.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.33314(9) 0.20103(5) 0.82419(13) 0.0318(3) Uani 1 1 d . . . . .
O3 O -0.2393(2) 0.35237(15) 0.7647(3) 0.0283(6) Uani 1 1 d . . . . .
C6 C 0.1642(4) 0.2468(2) 0.8049(5) 0.0230(7) Uani 1 1 d . . . . .
C4 C 0.0101(3) 0.3756(2) 0.7792(5) 0.0230(7) Uani 1 1 d . . . . .
H4 H -0.004204 0.438695 0.773173 0.028 Uiso 1 1 calc R . . . .
C5 C 0.1477(4) 0.3406(2) 0.7929(4) 0.0231(7) Uani 1 1 d . . . . .
O1 O -0.1835(3) 0.08002(16) 0.7725(4) 0.0388(7) Uani 1 1 d . . . . .
C3 C -0.1037(3) 0.3201(2) 0.7742(5) 0.0223(7) Uani 1 1 d . . . . .
C7 C 0.0496(4) 0.1918(2) 0.7968(4) 0.0243(7) Uani 1 1 d . . . . .
H7 H 0.063914 0.128673 0.802543 0.029 Uiso 1 1 calc R . . . .
O2 O -0.3393(3) 0.18994(16) 0.7453(5) 0.0438(7) Uani 1 1 d . . . . .
H2 H -0.339321 0.246216 0.750007 0.066 Uiso 1 1 calc GR . . . .
C2 C -0.0880(4) 0.2260(2) 0.7801(5) 0.0227(7) Uani 1 1 d . . . . .
N1 N 0.2610(3) 0.39502(18) 0.7972(4) 0.0310(7) Uani 1 1 d . . . . .
H1A H 0.304324 0.372456 0.719178 0.037 Uiso 1 1 d GR . . . .
H1B H 0.227998 0.447373 0.753247 0.037 Uiso 1 1 d GR . . . .
C1 C -0.2047(4) 0.1608(2) 0.7665(5) 0.0295(8) Uani 1 1 d . . . . .
C9 C -0.4168(4) 0.4601(2) 0.7660(5) 0.0292(8) Uani 1 1 d . . . . .
H9A H -0.439880 0.524196 0.761351 0.044 Uiso 1 1 calc R . . . .
H9B H -0.488123 0.429819 0.649026 0.044 Uiso 1 1 calc R . . . .
H9C H -0.421080 0.434260 0.893313 0.044 Uiso 1 1 calc R . . . .
C8 C -0.2649(4) 0.4478(2) 0.7572(5) 0.0255(7) Uani 1 1 d . . . . .
H8A H -0.258778 0.473412 0.629144 0.031 Uiso 1 1 calc R . . . .
H8B H -0.191382 0.477876 0.874718 0.031 Uiso 1 1 calc R . . . .


_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
Cl1 C6 1.738(3) . ?
O3 C3 1.381(4) . ?
O3 C8 1.443(4) . ?
C6 C5 1.408(4) . ?
C6 C7 1.368(4) . ?
C4 C5 1.406(4) . ?
C4 C3 1.372(4) . ?
C5 N1 1.358(4) . ?
O1 C1 1.221(4) . ?
C3 C2 1.411(4) . ?
C7 C2 1.396(4) . ?
O2 C1 1.335(4) . ?
C2 C1 1.470(5) . ?
C9 C8 1.506(4) . ?

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
C3 O3 C8 119.7(2) . . ?
C5 C6 Cl1 118.7(2) . . ?
C7 C6 Cl1 120.0(2) . . ?
C7 C6 C5 121.3(3) . . ?
C3 C4 C5 121.0(3) . . ?
C4 C5 C6 117.3(3) . . ?
N1 C5 C6 121.2(3) . . ?
N1 C5 C4 121.5(3) . . ?
O3 C3 C2 116.1(3) . . ?
C4 C3 O3 122.4(3) . . ?
C4 C3 C2 121.5(3) . . ?
C6 C7 C2 121.7(3) . . ?
C3 C2 C1 125.6(3) . . ?
C7 C2 C3 117.1(3) . . ?
C7 C2 C1 117.2(3) . . ?
O1 C1 O2 118.2(3) . . ?
O1 C1 C2 122.2(3) . . ?
O2 C1 C2 119.7(3) . . ?
O3 C8 C9 106.1(3) . . ?

_olex2_date_sample_data_collection 2018-11-14
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.137
_oxdiff_exptl_absorpt_empirical_full_min 0.875
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# 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_s4436na
_database_code_depnum_ccdc_archive 'CCDC 2009893'
loop_
_audit_author_name
_audit_author_address
'Sarah Wright'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#

_audit_creation_date             2016-03-18
_audit_creation_method           'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_cell_formula_units_Z            4
_cell_measurement_temperature    150.02(10)
_chemical_formula_sum            'C10 H9 F4 N O3'
_chemical_formula_weight         267.18

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'I 2/m'
_space_group_name_Hall           '-I 2y'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   6.5218(10)
_cell_length_b                   17.636(2)
_cell_length_c                   10.0639(14)
_cell_angle_alpha                90
_cell_angle_beta                 107.754(14)
_cell_angle_gamma                90
_cell_volume                     1102.4(3)
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.161
_exptl_crystal_density_diffrn    1.610
_diffrn_reflns_number            3925
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.320
_diffrn_reflns_theta_max         29.150
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1363
_reflns_number_gt                978
_reflns_threshold_expression     'I > 2σ(I)'
_cell_measurement_reflns_used    1261
_cell_measurement_theta_min      4.0420
_cell_measurement_theta_max      27.9050
_exptl_crystal_description       block
_exptl_crystal_colour            'translucent light white'
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.070
_exptl_absorpt_correction_T_min  0.73917
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.763
_oxdiff_exptl_absorpt_empirical_full_max 1.311
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.02(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 8.0714
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0507241000
_diffrn_orient_matrix_UB_12      0.0113941000
_diffrn_orient_matrix_UB_13      0.0498604000
_diffrn_orient_matrix_UB_21      0.0914564000
_diffrn_orient_matrix_UB_22      0.0221637000
_diffrn_orient_matrix_UB_23      0.0346000000
_diffrn_orient_matrix_UB_31      -0.0458732000
_diffrn_orient_matrix_UB_32      0.0315694000
_diffrn_orient_matrix_UB_33      -0.0423483000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  55.00   1.00    4.36    --  -17.77  37.00  90.00   95
  2  ω      0.00  36.00   1.00    4.36    --   18.86  77.00 -60.00   36
  3  ω    -87.00  12.00   1.00    4.36    --  -17.77 -77.00-180.00   99
  4  ω    -83.00   8.00   1.00    4.36    --  -17.77 -37.00 -90.00   91
  5  ω     32.00  60.00   1.00    4.36    --   18.86 -99.00  90.00   28
;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'C 1 2/m 1'
_symmetry_space_group_name_H-M   'I 1 2/m 1'
_symmetry_cell_setting           monoclinic
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1014P)²+1.0432P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1363
_refine_ls_number_parameters     98
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.2030
_refine_ls_wR_factor_gt          0.1822
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.7008(5) 0.5000 0.8959(3) 0.0221(7) Uani 1 2 d S T P . .
C2 C 0.4675(5) 0.5000 0.8209(3) 0.0206(7) Uani 1 2 d S T P . .
C3 C 0.3482(4) 0.56695(13) 0.7834(2) 0.0237(6) Uani 1 1 d . . . . .
C4 C 0.1320(4) 0.56650(13) 0.7146(2) 0.0229(6) Uani 1 1 d . . . . .
C5 C 0.0130(5) 0.5000 0.6761(3) 0.0205(7) Uani 1 2 d S T P . .
C6 C 0.5000 0.6991(2) 0.5000 0.0279(8) Uani 1 2 d S T P . .
C7 C 0.3214(6) 0.74380(19) 0.5230(5) 0.0580(10) Uani 1 1 d . . . . .
H7A H 0.2120 0.7100 0.5336 0.087 Uiso 1 1 calc R U . . .
H7B H 0.2613 0.7765 0.4445 0.087 Uiso 1 1 calc R U . . .
H7C H 0.3751 0.7739 0.6059 0.087 Uiso 1 1 calc R U . . .
F1 F 0.4404(3) 0.63473(8) 0.81472(18) 0.0364(5) Uani 1 1 d . . . . .
F2 F 0.0260(3) 0.63277(8) 0.68170(18) 0.0370(5) Uani 1 1 d . . . . .
N1 N -0.1994(5) 0.5000 0.6072(3) 0.0251(7) Uani 1 2 d S T P . .
O1 O 0.7959(3) 0.56311(11) 0.92644(19) 0.0320(5) Uani 1 1 d . . . . .
O2 O 0.5000 0.62956(14) 0.5000 0.0336(7) Uani 1 2 d S T P . .
H1A H -0.260(5) 0.5435(18) 0.587(3) 0.032(8) Uiso 1 1 d . . . . .
H1B H 0.928(12) 0.567(3) 0.949(6) 0.033(17) Uiso 0.5 1 d . . P . .


_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
C1 O1 1.266(2) 6_565 ?
C1 O1 1.266(2) . ?
C1 C2 1.478(5) . ?
C2 C3 1.401(3) . ?
C2 C3 1.401(3) 6_565 ?
C3 F1 1.332(3) . ?
C3 C4 1.368(4) . ?
C4 F2 1.347(3) . ?
C4 C5 1.394(3) . ?
C5 N1 1.347(4) . ?
C5 C4 1.394(3) 6_565 ?
C6 O2 1.227(4) . ?
C6 C7 1.482(4) 2_656 ?
C6 C7 1.482(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
N1 H1A 0.86(3) . ?
O1 H1B 0.82(7) . ?

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
O1 C1 O1 123.1(3) 6_565 . ?
O1 C1 C2 118.43(16) 6_565 . ?
O1 C1 C2 118.43(16) . . ?
C3 C2 C3 114.8(3) . 6_565 ?
C3 C2 C1 122.58(15) . . ?
C3 C2 C1 122.58(15) 6_565 . ?
F1 C3 C4 116.5(2) . . ?
F1 C3 C2 121.2(2) . . ?
C4 C3 C2 122.2(2) . . ?
F2 C4 C3 119.5(2) . . ?
F2 C4 C5 117.5(2) . . ?
C3 C4 C5 123.1(2) . . ?
N1 C5 C4 122.75(15) . 6_565 ?
N1 C5 C4 122.75(15) . . ?
C4 C5 C4 114.5(3) 6_565 . ?
O2 C6 C7 122.12(19) . 2_656 ?
O2 C6 C7 122.12(19) . . ?
C7 C6 C7 115.8(4) 2_656 . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 N1 H1A 117(2) . . ?
C1 O1 H1B 122(4) . . ?

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
O1 C1 C2 C3 179.6(3) 6_565 . . . ?
O1 C1 C2 C3 -0.4(5) . . . . ?
O1 C1 C2 C3 0.4(5) 6_565 . . 6_565 ?
O1 C1 C2 C3 -179.6(3) . . . 6_565 ?
C3 C2 C3 F1 178.85(15) 6_565 . . . ?
C1 C2 C3 F1 -0.4(4) . . . . ?
C3 C2 C3 C4 -0.4(5) 6_565 . . . ?
C1 C2 C3 C4 -179.7(2) . . . . ?
F1 C3 C4 F2 0.6(4) . . . . ?
C2 C3 C4 F2 179.8(2) . . . . ?
F1 C3 C4 C5 -179.4(2) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
F2 C4 C5 N1 0.7(4) . . . . ?
C3 C4 C5 N1 -179.3(3) . . . . ?
F2 C4 C5 C4 -179.33(15) . . . 6_565 ?
C3 C4 C5 C4 0.6(5) . . . 6_565 ?

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
C7 H7A F2 0.96 2.58 3.460(5) 152.7 .
C7 H7A F2 0.96 2.63 3.219(4) 120.2 2_556
C7 H7B F1 0.96 2.62 3.461(4) 146.3 8_464
C7 H7C F2 0.96 2.62 3.571(5) 172.1 7_566
N1 H1A O2 0.86(3) 2.16(3) 2.990(3) 161(3) 1_455
O1 H1B O1 0.82(7) 1.86(7) 2.622(4) 154(6) 2_757

_refine_diff_density_max         0.873
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.077


_chemical_name_systematic        
'4-amino-2,3,5,6-tetrafluorobenzoic acid acetone solvate'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone/Water'
####################################################################### 
# 
# 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_oacc35
_database_code_depnum_ccdc_archive 'CCDC 2009897'
loop_
_audit_author_name
_audit_author_address
'Sarah Wright'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2018-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        '4-amino-5-chloro-2-methoxybenzoic acid'
_chemical_formula_moiety         'C8 H8 Cl N O3'
_chemical_formula_sum            'C8 H8 Cl N O3'
_chemical_formula_weight         201.60
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 O3 N1 Cl1 H8'
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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2780(6)
_cell_length_b                   7.5330(7)
_cell_length_c                   16.2004(11)
_cell_angle_alpha                94.713(6)
_cell_angle_beta                 91.340(6)
_cell_angle_gamma                106.926(7)
_cell_volume                     845.80(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2223
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.0600
_cell_measurement_theta_min      3.9350
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.843
_exptl_absorpt_coefficient_mu    0.422
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.42044
_exptl_crystal_size_mid          0.14536
_exptl_crystal_size_min          0.06109
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7197
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.683
_diffrn_reflns_theta_min         3.612
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1636
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.823
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  33.00   1.00    4.53    --   10.40 -57.00-120.00   94
  2  ω    -16.00  78.00   1.00    4.53    --   10.40  57.00  30.00   94
  3  ω    -74.00 -43.00   1.00    4.53    --   10.40 178.00   0.00   31
  4  ω    -23.00  45.00   1.00    4.53    --   10.40 -99.00 150.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0075528000
_diffrn_orient_matrix_UB_12      0.0920600000
_diffrn_orient_matrix_UB_13      0.0039107000
_diffrn_orient_matrix_UB_21      0.0987029000
_diffrn_orient_matrix_UB_22      0.0346767000
_diffrn_orient_matrix_UB_23      0.0129740000
_diffrn_orient_matrix_UB_31      0.0245775000
_diffrn_orient_matrix_UB_32      0.0096897000
_diffrn_orient_matrix_UB_33      -0.0418463000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2562
_reflns_number_total             3951
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3951
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      0.935
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1794
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Rotating group:
 N2(H2a), N1(H1a,H1b)
2.b Me refined with riding coordinates:
 C16(H16a,H16b,H16c), C17(H17a,H17b,H17c)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C10(H10), C1(H1), C4(H4)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.28999(12) 0.83788(11) 0.07046(5) 0.0316(2) Uani 1 1 d . . . . .
O1 O 0.6828(3) 1.1846(3) 0.38926(13) 0.0283(5) Uani 1 1 d . . . . .
C9 C 0.4951(4) 1.1386(4) 0.17221(19) 0.0220(6) Uani 1 1 d . . . . .
C13 C 0.4159(4) 0.8392(4) 0.22795(18) 0.0216(6) Uani 1 1 d . . . . .
H13 H 0.357328 0.708334 0.219791 0.026 Uiso 1 1 calc R . . . .
O4 O 0.4371(4) 0.6213(3) 0.35598(15) 0.0386(6) Uani 1 1 d . . . . .
O3 O 0.5851(3) 0.8591(3) 0.44352(14) 0.0335(6) Uani 1 1 d . . . . .
H3 H 0.614527 0.975949 0.446674 0.050 Uiso 1 1 calc GR . . . .
C12 C 0.5071(4) 0.9172(4) 0.30451(19) 0.0230(7) Uani 1 1 d . . . . .
C8 C 0.4082(4) 0.9452(4) 0.16425(18) 0.0232(7) Uani 1 1 d . . . . .
C11 C 0.5940(4) 1.1120(4) 0.31313(18) 0.0221(6) Uani 1 1 d . . . . .
N2 N 0.4863(4) 1.2465(4) 0.10988(17) 0.0316(7) Uani 1 1 d . . . . .
H2A H 0.444070 1.173606 0.065426 0.038 Uiso 1 1 d GR . . . .
C14 C 0.5056(5) 0.7892(4) 0.3688(2) 0.0263(7) Uani 1 1 d . . . . .
C10 C 0.5882(4) 1.2190(4) 0.24888(18) 0.0223(7) Uani 1 1 d . . . . .
H10 H 0.648354 1.349637 0.256561 0.027 Uiso 1 1 calc R . . . .
C16 C 0.7702(5) 1.3816(4) 0.4040(2) 0.0349(8) Uani 1 1 d . . . . .
H16A H 0.827268 1.411886 0.460685 0.052 Uiso 1 1 calc R . . . .
H16B H 0.870729 1.421850 0.364523 0.052 Uiso 1 1 calc R . . . .
H16C H 0.672515 1.445982 0.396865 0.052 Uiso 1 1 calc R . . . .
Cl2 Cl 0.07307(12) 0.84596(11) 0.42525(5) 0.0307(2) Uani 1 1 d . . . . .
O2 O -0.0264(3) 1.1798(3) 0.11913(13) 0.0309(5) Uani 1 1 d . . . . .
C1 C -0.0602(4) 0.8422(4) 0.26876(19) 0.0236(7) Uani 1 1 d . . . . .
H1 H -0.115976 0.712457 0.272345 0.028 Uiso 1 1 calc R . . . .
C5 C 0.1264(4) 1.1433(4) 0.33491(19) 0.0224(6) Uani 1 1 d . . . . .
O5 O -0.2666(4) 0.6228(3) 0.13315(15) 0.0414(6) Uani 1 1 d . . . . .
O6 O -0.2173(4) 0.8533(3) 0.05417(14) 0.0358(6) Uani 1 1 d . . . . .
H6 H -0.172580 0.969993 0.059056 0.054 Uiso 1 1 calc GR . . . .
N1 N 0.2270(4) 1.2527(4) 0.40088(16) 0.0292(6) Uani 1 1 d . . . . .
H1A H 0.272210 1.372521 0.409193 0.035 Uiso 1 1 d GR . . . .
H1B H 0.215020 1.205442 0.447923 0.035 Uiso 1 1 d GR . . . .
C6 C 0.0425(4) 0.9509(4) 0.33635(18) 0.0222(7) Uani 1 1 d . . . . .
C2 C -0.0844(4) 0.9179(4) 0.19491(18) 0.0226(7) Uani 1 1 d . . . . .
C4 C 0.1014(4) 1.2196(4) 0.26064(19) 0.0241(7) Uani 1 1 d . . . . .
H4 H 0.155862 1.349583 0.257261 0.029 Uiso 1 1 calc R . . . .
C3 C 0.0000(4) 1.1104(4) 0.19273(18) 0.0223(7) Uani 1 1 d . . . . .
C7 C -0.1958(5) 0.7879(4) 0.1267(2) 0.0284(7) Uani 1 1 d . . . . .
C17 C 0.0592(6) 1.3753(4) 0.1112(2) 0.0364(8) Uani 1 1 d . . . . .
H17A H 0.027895 1.403564 0.055543 0.055 Uiso 1 1 calc R . . . .
H17B H 0.008975 1.448735 0.152690 0.055 Uiso 1 1 calc R . . . .
H17C H 0.199149 1.406550 0.119931 0.055 Uiso 1 1 calc R . . . .
H2B H 0.554(5) 1.365(5) 0.112(2) 0.040(10) Uiso 1 1 d . . . . .


_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
Cl1 C8 1.742(3) . ?
O1 C11 1.373(4) . ?
O1 C16 1.432(4) . ?
C9 C8 1.403(4) . ?
C9 N2 1.359(4) . ?
C9 C10 1.402(4) . ?
C13 C12 1.392(4) . ?
C13 C8 1.365(4) . ?
O4 C14 1.215(4) . ?
O3 C14 1.328(4) . ?
C12 C11 1.412(4) . ?
C12 C14 1.474(4) . ?
C11 C10 1.375(4) . ?
Cl2 C6 1.739(3) . ?
O2 C3 1.372(4) . ?
O2 C17 1.440(4) . ?
C1 C6 1.374(4) . ?
C1 C2 1.396(4) . ?
C5 N1 1.351(4) . ?
C5 C6 1.402(4) . ?
C5 C4 1.405(4) . ?
O5 C7 1.214(4) . ?
O6 C7 1.334(4) . ?
C2 C3 1.404(4) . ?
C2 C7 1.468(4) . ?
C4 C3 1.375(4) . ?

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
C11 O1 C16 119.0(2) . . ?
N2 C9 C8 122.3(3) . . ?
N2 C9 C10 120.6(3) . . ?
C10 C9 C8 117.1(3) . . ?
C8 C13 C12 122.0(3) . . ?
C13 C12 C11 116.8(3) . . ?
C13 C12 C14 117.2(3) . . ?
C11 C12 C14 126.0(3) . . ?
C9 C8 Cl1 119.1(2) . . ?
C13 C8 Cl1 119.4(2) . . ?
C13 C8 C9 121.5(3) . . ?
O1 C11 C12 115.4(3) . . ?
O1 C11 C10 123.2(3) . . ?
C10 C11 C12 121.4(3) . . ?
O4 C14 O3 118.3(3) . . ?
O4 C14 C12 122.8(3) . . ?
O3 C14 C12 119.0(3) . . ?
C11 C10 C9 121.2(3) . . ?
C3 O2 C17 119.0(3) . . ?
C6 C1 C2 121.5(3) . . ?
N1 C5 C6 122.6(3) . . ?
N1 C5 C4 120.7(3) . . ?
C6 C5 C4 116.7(3) . . ?
C1 C6 Cl2 119.0(2) . . ?
C1 C6 C5 121.7(3) . . ?
C5 C6 Cl2 119.3(2) . . ?
C1 C2 C3 117.2(3) . . ?
C1 C2 C7 116.6(3) . . ?
C3 C2 C7 126.2(3) . . ?
C3 C4 C5 121.5(3) . . ?
O2 C3 C2 115.5(3) . . ?
O2 C3 C4 123.1(3) . . ?
C4 C3 C2 121.4(3) . . ?
O5 C7 O6 118.6(3) . . ?
O5 C7 C2 122.7(3) . . ?
O6 C7 C2 118.6(3) . . ?

_olex2_date_sample_data_collection 2018-11-14
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.117
_oxdiff_exptl_absorpt_empirical_full_min 0.893
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# 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_oacc12
_database_code_depnum_ccdc_archive 'CCDC 2009894'
loop_
_audit_author_name
_audit_author_address
'Sarah Wright'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2018-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        '4-amino-3-chlorobenzoic acid'
_chemical_formula_moiety         'C7 H6 Cl N O2'
_chemical_formula_sum            'C7 H6 Cl N O2'
_chemical_formula_weight         171.58
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C7 O2 N Cl H6'
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'
Cl Cl 0.1484 0.1585 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.7229(3)
_cell_length_b                   11.1634(8)
_cell_length_c                   16.9454(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.218(7)
_cell_angle_gamma                90
_cell_volume                     701.34(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2173
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.5220
_cell_measurement_theta_min      4.0670
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.779
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.543
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.102
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5117
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.582
_diffrn_reflns_theta_min         3.650
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1636
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  99.00   1.00    7.50    --   10.40 178.00 -30.00   64
  2  ω    -83.00  14.00   1.00    7.50    --  -11.10 -57.00 -30.00   97
  3  ω    -39.00  56.00   1.00    7.50    --  -11.10  57.00 120.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1036907000
_diffrn_orient_matrix_UB_12      -0.0310340000
_diffrn_orient_matrix_UB_13      0.0306965000
_diffrn_orient_matrix_UB_21      -0.0315532000
_diffrn_orient_matrix_UB_22      -0.0546446000
_diffrn_orient_matrix_UB_23      -0.0208126000
_diffrn_orient_matrix_UB_31      0.1578620000
_diffrn_orient_matrix_UB_32      0.0094131000
_diffrn_orient_matrix_UB_33      -0.0196924000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1342
_reflns_number_total             1728
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1728
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+0.1433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.1027
_refine_special_details          ?
_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.a Rotating group:
 N1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C6(H6)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.39931(14) 0.94089(4) 0.09573(3) 0.02610(18) Uani 1 1 d . . . . .
O1 O 0.5085(4) 0.94674(12) 0.40901(8) 0.0321(4) Uani 1 1 d . . . . .
O2 O 0.2973(4) 1.12486(13) 0.44513(8) 0.0332(4) Uani 1 1 d . . . . .
H2 H 0.346468 1.095822 0.490563 0.050 Uiso 1 1 calc GR . . . .
C3 C 0.2944(5) 1.03898(16) 0.17027(11) 0.0188(4) Uani 1 1 d . . . . .
C2 C 0.3740(5) 1.00686(17) 0.24824(11) 0.0194(4) Uani 1 1 d . . . . .
H2A H 0.487790 0.932265 0.260918 0.023 Uiso 1 1 calc R . . . .
C1 C 0.2884(5) 1.08330(17) 0.30861(11) 0.0198(4) Uani 1 1 d . . . . .
N1 N 0.0584(5) 1.18245(16) 0.07173(10) 0.0329(5) Uani 1 1 d . . . . .
H1A H -0.049800 1.249172 0.060041 0.039 Uiso 1 1 d GR . . . .
H1B H 0.099541 1.143898 0.029491 0.039 Uiso 1 1 d GR . . . .
C7 C 0.3739(6) 1.04613(17) 0.39144(12) 0.0239(5) Uani 1 1 d . . . . .
C5 C 0.0513(6) 1.22548(17) 0.21058(12) 0.0233(5) Uani 1 1 d . . . . .
H5 H -0.057606 1.300923 0.198151 0.028 Uiso 1 1 calc R . . . .
C6 C 0.1257(5) 1.19354(17) 0.28863(12) 0.0229(4) Uani 1 1 d . . . . .
H6 H 0.066390 1.246612 0.329304 0.027 Uiso 1 1 calc R . . . .
C4 C 0.1322(5) 1.14937(17) 0.14886(11) 0.0221(4) Uani 1 1 d . . . . .


_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
Cl1 C3 1.7426(19) . ?
O1 C7 1.242(2) . ?
O2 C7 1.315(2) . ?
C3 C2 1.375(3) . ?
C3 C4 1.405(3) . ?
C2 C1 1.391(3) . ?
C1 C7 1.471(3) . ?
C1 C6 1.400(3) . ?
N1 C4 1.362(3) . ?
C5 C6 1.373(3) . ?
C5 C4 1.401(3) . ?

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
C2 C3 Cl1 119.32(15) . . ?
C2 C3 C4 121.78(18) . . ?
C4 C3 Cl1 118.90(15) . . ?
C3 C2 C1 120.19(18) . . ?
C2 C1 C7 118.99(17) . . ?
C2 C1 C6 118.98(17) . . ?
C6 C1 C7 122.03(17) . . ?
O1 C7 O2 122.63(18) . . ?
O1 C7 C1 121.89(18) . . ?
O2 C7 C1 115.48(17) . . ?
C6 C5 C4 121.54(18) . . ?
C5 C6 C1 120.41(18) . . ?
N1 C4 C3 122.01(19) . . ?
N1 C4 C5 120.90(18) . . ?
C5 C4 C3 117.09(18) . . ?

_olex2_date_sample_data_collection 2018-10-19
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.675
_oxdiff_exptl_absorpt_empirical_full_min 0.460
####################################################################### 
# 
# 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_oacc11
_database_code_depnum_ccdc_archive 'CCDC 2009892'
loop_
_audit_author_name
_audit_author_address
'Sarah Wright'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2018-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        '4-amino-2-methoxybenzoic acid'
_chemical_formula_moiety         'C8 H9 N O3'
_chemical_formula_sum            'C8 H9 N O3'
_chemical_formula_weight         167.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 O3 N H9'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1846(7)
_cell_length_b                   13.5952(10)
_cell_length_c                   7.2087(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.909(10)
_cell_angle_gamma                90
_cell_volume                     754.18(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1787
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.1090
_cell_measurement_theta_min      3.9810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.1687
2 2 -5 0.1129
-2 -2 5 0.0299
-1 0 0 0.1436
1 0 0 0.2116
0 -1 0 0.1687

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.355
_exptl_crystal_size_min          0.143
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0003 0.9992 0.0001 0.0160 -0.0309 0.0388
1.9969 1.9997 -4.9921 0.4928 0.0958 0.0127
-1.9969 -1.9997 4.9921 -0.4928 -0.0958 -0.0127
-0.9991 0.0002 -0.0003 -0.0158 0.0676 0.0605
0.9991 -0.0002 0.0003 0.0158 -0.0676 -0.0605
0.0003 -0.9992 -0.0001 -0.0160 0.0309 -0.0388

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5879
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.544
_diffrn_reflns_theta_min         3.359
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1636
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  59.00   1.00    2.79    --  -11.10  57.00 120.00   93
  2  ω    -67.00  13.00   1.00    2.79    --  -11.10 -77.00-150.00   80
  3  ω    -80.00  16.00   1.00    2.79    --  -11.10 -57.00 -30.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0158922000
_diffrn_orient_matrix_UB_12      0.0160643000
_diffrn_orient_matrix_UB_13      -0.0859259000
_diffrn_orient_matrix_UB_21      -0.0676207000
_diffrn_orient_matrix_UB_22      -0.0309661000
_diffrn_orient_matrix_UB_23      -0.0586406000
_diffrn_orient_matrix_UB_31      -0.0605906000
_diffrn_orient_matrix_UB_32      0.0387921000
_diffrn_orient_matrix_UB_33      -0.0112394000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1219
_reflns_number_total             1877
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1877
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0532
_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)+(0.0579P)²+0.1082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1382
_refine_special_details          ?
_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 C(H,H,H) groups, All O(H) groups
2.a Rotating group:
 N1(H1A,H1B)
2.b Me refined with riding coordinates:
 C8(H8A,H8B,H8C)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6)
2.d 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
O3 O 0.79915(15) 0.56392(9) 0.3617(2) 0.0272(4) Uani 1 1 d . . . . .
O2 O 0.95738(16) 0.73033(10) 0.4289(2) 0.0351(4) Uani 1 1 d . . . . .
H2 H 0.940049 0.672200 0.398125 0.053 Uiso 1 1 calc GR . . . .
O1 O 0.81292(17) 0.85906(10) 0.4711(2) 0.0343(4) Uani 1 1 d . . . . .
N1 N 0.17826(19) 0.55985(12) 0.2055(2) 0.0294(4) Uani 1 1 d . . . . .
H1A H 0.170913 0.502418 0.151275 0.035 Uiso 1 1 d GR . . . .
H1B H 0.084461 0.592919 0.147948 0.035 Uiso 1 1 d GR . . . .
C2 C 0.6444(2) 0.60964(13) 0.3408(3) 0.0220(4) Uani 1 1 d . . . . .
C1 C 0.6525(2) 0.71071(13) 0.3841(3) 0.0223(4) Uani 1 1 d . . . . .
C4 C 0.3333(2) 0.60935(14) 0.2631(3) 0.0236(4) Uani 1 1 d . . . . .
C3 C 0.4874(2) 0.55971(13) 0.2821(3) 0.0232(4) Uani 1 1 d . . . . .
H3 H 0.484770 0.492707 0.255199 0.028 Uiso 1 1 calc R . . . .
C5 C 0.3407(2) 0.70959(14) 0.3127(3) 0.0257(4) Uani 1 1 d . . . . .
H5 H 0.239799 0.743196 0.305596 0.031 Uiso 1 1 calc R . . . .
C6 C 0.4967(2) 0.75749(14) 0.3714(3) 0.0251(4) Uani 1 1 d . . . . .
H6 H 0.499504 0.823772 0.404197 0.030 Uiso 1 1 calc R . . . .
C7 C 0.8098(2) 0.77155(14) 0.4309(3) 0.0256(4) Uani 1 1 d . . . . .
C8 C 0.7960(2) 0.46509(13) 0.2924(3) 0.0288(5) Uani 1 1 d . . . . .
H8A H 0.912810 0.442878 0.316708 0.043 Uiso 1 1 calc R . . . .
H8B H 0.740774 0.423226 0.360609 0.043 Uiso 1 1 calc R . . . .
H8C H 0.732354 0.462859 0.153330 0.043 Uiso 1 1 calc R . . . .


_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
O3 C2 1.372(2) . ?
O3 C8 1.431(2) . ?
O2 C7 1.336(2) . ?
O1 C7 1.223(2) . ?
N1 C4 1.370(2) . ?
C2 C1 1.406(3) . ?
C2 C3 1.385(2) . ?
C1 C6 1.400(2) . ?
C1 C7 1.469(2) . ?
C4 C3 1.396(2) . ?
C4 C5 1.405(3) . ?
C5 C6 1.366(3) . ?

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
C2 O3 C8 118.73(14) . . ?
O3 C2 C1 116.48(15) . . ?
O3 C2 C3 122.47(16) . . ?
C3 C2 C1 121.05(16) . . ?
C2 C1 C7 124.97(16) . . ?
C6 C1 C2 117.13(16) . . ?
C6 C1 C7 117.81(16) . . ?
N1 C4 C3 120.34(17) . . ?
N1 C4 C5 120.61(16) . . ?
C3 C4 C5 118.99(16) . . ?
C2 C3 C4 120.40(17) . . ?
C6 C5 C4 119.76(16) . . ?
C5 C6 C1 122.57(17) . . ?
O2 C7 C1 119.07(16) . . ?
O1 C7 O2 117.69(16) . . ?
O1 C7 C1 123.24(17) . . ?

_olex2_date_sample_data_collection 2018-10-19
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.301
_oxdiff_exptl_absorpt_empirical_full_min 0.913
####################################################################### 
# 
# 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_c2c
_database_code_depnum_ccdc_archive 'CCDC 2009895'
loop_
_audit_author_name
_audit_author_address
'Sarah Wright'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2020-06-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        '4-amino-2-fluorobenzoic acid'
_chemical_formula_moiety         'C7 H6 F N O2'
_chemical_formula_sum            'C7 H6 F N O2'
_chemical_formula_weight         155.13
_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'
F F 0.0171 0.0103 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.7711(8)
_cell_length_b                   3.7877(2)
_cell_length_c                   24.3334(12)
_cell_angle_alpha                90
_cell_angle_beta                 107.378(4)
_cell_angle_gamma                90
_cell_volume                     1299.28(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3882
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.6860
_cell_measurement_theta_min      2.8730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.30c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.068
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            7607
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.021
_diffrn_reflns_theta_min         2.890
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1386
_reflns_number_total             1554
_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       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1554
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.081
_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)+(0.0558P)²+1.0215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1098
_refine_special_details          ?
_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.a Riding coordinates:
 O2(H2), N9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
F6 F -0.09166(5) 0.3267(2) 0.16896(3) 0.0315(2) Uani 1 1 d . . . . .
O1 O -0.13436(6) 0.8325(3) 0.01065(4) 0.0273(3) Uani 1 1 d . . . . .
O2 O -0.20337(6) 0.5639(3) 0.06950(4) 0.0290(3) Uani 1 1 d . . . . .
H2 H -0.251760 0.603261 0.042215 0.044 Uiso 1 1 d R . . . .
N9 N 0.23994(7) 0.2924(3) 0.19666(4) 0.0252(3) Uani 1 1 d . . . . .
H9A H 0.244516 0.117464 0.220398 0.030 Uiso 1 1 d R . . . .
H9B H 0.280526 0.269014 0.177508 0.030 Uiso 1 1 d R . . . .
C3 C -0.12957(8) 0.6636(3) 0.05619(5) 0.0187(3) Uani 1 1 d . . . . .
C4 C -0.03490(8) 0.5761(3) 0.09538(5) 0.0177(3) Uani 1 1 d . . . . .
C5 C -0.01812(8) 0.4090(3) 0.14855(5) 0.0199(3) Uani 1 1 d . . . . .
C7 C 0.07097(8) 0.3164(3) 0.18289(5) 0.0206(3) Uani 1 1 d . . . . .
H7 H 0.078955 0.209337 0.218417 0.025 Uiso 1 1 calc R . . . .
C8 C 0.14940(8) 0.3861(3) 0.16344(5) 0.0191(3) Uani 1 1 d . . . . .
C10 C 0.13549(8) 0.5624(3) 0.11094(5) 0.0196(3) Uani 1 1 d . . . . .
H10 H 0.187311 0.618173 0.098325 0.023 Uiso 1 1 calc R . . . .
C11 C 0.04538(8) 0.6535(3) 0.07793(5) 0.0186(3) Uani 1 1 d . . . . .
H11 H 0.037461 0.769477 0.043124 0.022 Uiso 1 1 calc R . . . .


_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
F6 C5 1.3587(13) . ?
O1 C3 1.2630(14) . ?
O2 H2 0.8310 . ?
O2 C3 1.2834(14) . ?
N9 H9A 0.8683 . ?
N9 H9B 0.8668 . ?
N9 C8 1.3864(15) . ?
C3 C4 1.4759(15) . ?
C4 C5 1.3945(16) . ?
C4 C11 1.4046(15) . ?
C5 C7 1.3769(16) . ?
C7 H7 0.9300 . ?
C7 C8 1.4011(16) . ?
C8 C10 1.4013(17) . ?
C10 H10 0.9300 . ?
C10 C11 1.3774(16) . ?
C11 H11 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
C3 O2 H2 109.8 . . ?
H9A N9 H9B 110.5 . . ?
C8 N9 H9A 116.9 . . ?
C8 N9 H9B 114.5 . . ?
O1 C3 O2 122.77(10) . . ?
O1 C3 C4 118.34(10) . . ?
O2 C3 C4 118.89(10) . . ?
C5 C4 C3 124.96(10) . . ?
C5 C4 C11 116.30(10) . . ?
C11 C4 C3 118.70(10) . . ?
F6 C5 C4 120.21(10) . . ?
F6 C5 C7 116.32(10) . . ?
C7 C5 C4 123.46(11) . . ?
C5 C7 H7 120.5 . . ?
C5 C7 C8 118.93(11) . . ?
C8 C7 H7 120.5 . . ?
N9 C8 C7 120.38(11) . . ?
N9 C8 C10 120.45(11) . . ?
C10 C8 C7 119.14(10) . . ?
C8 C10 H10 119.9 . . ?
C11 C10 C8 120.26(10) . . ?
C11 C10 H10 119.9 . . ?
C4 C11 H11 119.1 . . ?
C10 C11 C4 121.84(11) . . ?
C10 C11 H11 119.1 . . ?

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
F6 C5 C7 C8 178.35(10) . . . . ?
O1 C3 C4 C5 176.23(12) . . . . ?
O1 C3 C4 C11 -6.04(17) . . . . ?
O2 C3 C4 C5 -4.16(19) . . . . ?
O2 C3 C4 C11 173.57(11) . . . . ?
N9 C8 C10 C11 179.67(11) . . . . ?
C3 C4 C5 F6 -2.70(19) . . . . ?
C3 C4 C5 C7 176.89(11) . . . . ?
C3 C4 C11 C10 -176.54(11) . . . . ?
C4 C5 C7 C8 -1.25(19) . . . . ?
C5 C4 C11 C10 1.38(18) . . . . ?
C5 C7 C8 N9 -179.22(11) . . . . ?
C5 C7 C8 C10 2.92(18) . . . . ?
C7 C8 C10 C11 -2.47(18) . . . . ?
C8 C10 C11 C4 0.28(18) . . . . ?
C11 C4 C5 F6 179.52(10) . . . . ?
C11 C4 C5 C7 -0.89(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
####################################################################### 
# 
# 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_s4474mat
_database_code_depnum_ccdc_archive 'CCDC 2009898'
loop_
_audit_author_name
_audit_author_address
'Sarah Wright'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------# 

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-aminobenzoic acid dioxane solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N2 O6'
_chemical_formula_weight         362.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.4397(9)
_cell_length_b                   20.5326(7)
_cell_length_c                   11.9083(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.194(3)
_cell_angle_gamma                90
_cell_volume                     5294.9(3)
_cell_formula_units_Z            12
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2106
_cell_measurement_theta_min      4.31
_cell_measurement_theta_max      71.91

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             2304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.862
_shelx_estimated_absorpt_T_min   0.807
_shelx_estimated_absorpt_T_max   0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77675
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10342
_diffrn_reflns_av_unetI/netI     0.0943
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.040
_diffrn_reflns_theta_max         72.364
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             10342
_reflns_number_gt                6217
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0818P)²+6.4938P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10342
_refine_ls_number_parameters     722
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0801
_refine_ls_wR_factor_ref         0.2386
_refine_ls_wR_factor_gt          0.2062
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.16898(19) 0.5876(2) 0.2727(4) 0.0291(9) Uani 1 1 d . . . . .
C2 C 0.16710(18) 0.6545(2) 0.2272(4) 0.0273(8) Uani 1 1 d . . . . .
C3 C 0.14257(19) 0.7058(2) 0.2781(4) 0.0286(9) Uani 1 1 d . . . . .
H3 H 0.1261 0.6973 0.3425 0.034 Uiso 1 1 calc R U . . .
C4 C 0.14184(19) 0.7686(2) 0.2366(4) 0.0301(9) Uani 1 1 d . . . . .
H4 H 0.1243 0.8026 0.2715 0.036 Uiso 1 1 calc R U . . .
C5 C 0.1669(2) 0.7822(2) 0.1428(4) 0.0313(9) Uani 1 1 d . . . . .
C6 C 0.1914(2) 0.7305(2) 0.0907(4) 0.0310(9) Uani 1 1 d . . . . .
H6 H 0.2080 0.7387 0.0265 0.037 Uiso 1 1 calc R U . . .
C7 C 0.19118(19) 0.6679(2) 0.1332(4) 0.0285(9) Uani 1 1 d . . . . .
H7 H 0.2078 0.6334 0.0976 0.034 Uiso 1 1 calc R U . . .
C8 C 0.17400(19) 0.4124(2) 0.3960(4) 0.0286(9) Uani 1 1 d . . . . .
C9 C 0.17162(18) 0.3458(2) 0.4380(3) 0.0257(8) Uani 1 1 d . . . . .
C10 C 0.19216(18) 0.2931(2) 0.3841(4) 0.0280(9) Uani 1 1 d . . . . .
H10 H 0.2086 0.3005 0.3194 0.034 Uiso 1 1 calc R U . . .
C11 C 0.18894(19) 0.2303(2) 0.4235(4) 0.0300(9) Uani 1 1 d . . . . .
H11 H 0.2034 0.1951 0.3860 0.036 Uiso 1 1 calc R U . . .
C12 C 0.1645(2) 0.2179(2) 0.5184(4) 0.0314(9) Uani 1 1 d . . . . .
C13 C 0.1441(2) 0.2708(2) 0.5726(4) 0.0317(9) Uani 1 1 d . . . . .
H13 H 0.1277 0.2635 0.6374 0.038 Uiso 1 1 calc R U . . .
C14 C 0.14767(19) 0.3336(2) 0.5329(4) 0.0289(9) Uani 1 1 d . . . . .
H14 H 0.1336 0.3689 0.5707 0.035 Uiso 1 1 calc R U . . .
C15 C 0.32395(19) 0.0865(2) 0.2181(3) 0.0299(9) Uani 1 1 d . . . . .
C16 C 0.32702(19) 0.1530(2) 0.2630(4) 0.0293(9) Uani 1 1 d . . . . .
C17 C 0.30687(19) 0.2062(2) 0.1891(4) 0.0302(9) Uani 1 1 d . . . . .
H17 H 0.2896 0.1992 0.1082 0.036 Uiso 1 1 calc R U . . .
C18 C 0.31197(19) 0.2684(2) 0.2329(4) 0.0307(9) Uani 1 1 d . . . . .
H18 H 0.2977 0.3038 0.1817 0.037 Uiso 1 1 calc R U . . .
C19 C 0.33784(19) 0.2809(2) 0.3517(4) 0.0325(9) Uani 1 1 d . . . . .
C20 C 0.3575(2) 0.2273(2) 0.4264(4) 0.0333(9) Uani 1 1 d . . . . .
H20 H 0.3745 0.2341 0.5074 0.040 Uiso 1 1 calc R U . . .
C21 C 0.35191(19) 0.1652(2) 0.3817(4) 0.0320(9) Uani 1 1 d . . . . .
H21 H 0.3654 0.1296 0.4328 0.038 Uiso 1 1 calc R U . . .
C22 C 0.6761(2) 0.4105(2) 0.3934(3) 0.0309(9) Uani 1 1 d . . . . .
C23 C 0.67269(19) 0.3441(2) 0.4361(4) 0.0287(9) Uani 1 1 d . . . . .
C24 C 0.69607(19) 0.3297(2) 0.5537(4) 0.0307(9) Uani 1 1 d . . . . .
H24 H 0.7133 0.3637 0.6063 0.037 Uiso 1 1 calc R U . . .
C25 C 0.69483(19) 0.2675(2) 0.5955(3) 0.0300(9) Uani 1 1 d . . . . .
H25 H 0.7111 0.2590 0.6762 0.036 Uiso 1 1 calc R U . . .
C26 C 0.6698(2) 0.2165(2) 0.5199(4) 0.0314(9) Uani 1 1 d . . . . .
C27 C 0.6455(2) 0.2312(2) 0.4015(4) 0.0325(9) Uani 1 1 d . . . . .
H27 H 0.6273 0.1975 0.3491 0.039 Uiso 1 1 calc R U . . .
C28 C 0.6474(2) 0.2930(2) 0.3600(4) 0.0297(9) Uani 1 1 d . . . . .
H28 H 0.6316 0.3015 0.2793 0.036 Uiso 1 1 calc R U . . .
C29 C 0.0045(2) 0.4113(2) 0.0539(4) 0.0332(9) Uani 1 1 d . . . . .
C30 C 0.00436(19) 0.3447(2) 0.0982(4) 0.0303(9) Uani 1 1 d . . . . .
C31 C 0.0297(2) 0.3308(2) 0.2162(4) 0.0338(10) Uani 1 1 d . . . . .
H31 H 0.0469 0.3651 0.2681 0.041 Uiso 1 1 calc R U . . .
C32 C 0.0301(2) 0.2687(3) 0.2582(4) 0.0343(10) Uani 1 1 d . . . . .
H32 H 0.0474 0.2603 0.3386 0.041 Uiso 1 1 calc R U . . .
C33 C 0.0049(2) 0.2172(2) 0.1829(4) 0.0342(10) Uani 1 1 d . . . . .
C34 C -0.0212(2) 0.2309(2) 0.0650(4) 0.0336(10) Uani 1 1 d . . . . .
H34 H -0.0386 0.1966 0.0131 0.040 Uiso 1 1 calc R U . . .
C35 C -0.0218(2) 0.2937(2) 0.0238(4) 0.0337(10) Uani 1 1 d . . . . .
H35 H -0.0403 0.3024 -0.0561 0.040 Uiso 1 1 calc R U . . .
C36 C 0.4962(2) 0.0891(2) 0.0484(4) 0.0340(10) Uani 1 1 d . . . . .
C37 C 0.49713(19) 0.1558(2) 0.0925(4) 0.0307(9) Uani 1 1 d . . . . .
C38 C 0.47103(19) 0.1704(2) 0.1846(4) 0.0330(10) Uani 1 1 d . . . . .
H38 H 0.4525 0.1367 0.2185 0.040 Uiso 1 1 calc R U . . .
C39 C 0.4721(2) 0.2332(2) 0.2264(4) 0.0340(10) Uani 1 1 d . . . . .
H39 H 0.4546 0.2422 0.2892 0.041 Uiso 1 1 calc R U . . .
C40 C 0.4985(2) 0.2833(2) 0.1776(4) 0.0326(9) Uani 1 1 d . . . . .
C41 C 0.52489(19) 0.2687(2) 0.0851(4) 0.0327(9) Uani 1 1 d . . . . .
H41 H 0.5430 0.3025 0.0509 0.039 Uiso 1 1 calc R U . . .
C42 C 0.52474(19) 0.2058(2) 0.0439(4) 0.0309(9) Uani 1 1 d . . . . .
H42 H 0.5434 0.1965 -0.0173 0.037 Uiso 1 1 calc R U . . .
C43 C 0.3306(2) 0.4429(2) 0.1267(4) 0.0396(11) Uani 1 1 d . . . . .
H43A H 0.3011 0.4121 0.0774 0.048 Uiso 1 1 calc R U . . .
H43B H 0.3722 0.4230 0.1446 0.048 Uiso 1 1 calc R U . . .
C44 C 0.3308(3) 0.5053(2) 0.0615(4) 0.0462(12) Uani 1 1 d . . . . .
H44A H 0.3447 0.4966 -0.0094 0.055 Uiso 1 1 calc R U . . .
H44B H 0.2884 0.5230 0.0371 0.055 Uiso 1 1 calc R U . . .
C45 C 0.3532(2) 0.5634(2) 0.2358(4) 0.0399(11) Uani 1 1 d . . . . .
H45A H 0.3112 0.5825 0.2175 0.048 Uiso 1 1 calc R U . . .
H45B H 0.3822 0.5947 0.2850 0.048 Uiso 1 1 calc R U . . .
C46 C 0.3539(3) 0.5006(3) 0.3008(5) 0.0516(14) Uani 1 1 d . . . . .
H46A H 0.3964 0.4831 0.3235 0.062 Uiso 1 1 calc R U . . .
H46B H 0.3409 0.5090 0.3728 0.062 Uiso 1 1 calc R U . . .
C47 C 0.1781(3) 0.5045(3) 0.7303(5) 0.0462(12) Uani 1 1 d . . . . .
H47A H 0.2204 0.5227 0.7541 0.055 Uiso 1 1 calc R U . . .
H47B H 0.1680 0.4951 0.6458 0.055 Uiso 1 1 calc R U . . .
C48 C 0.1757(3) 0.4423(3) 0.7959(4) 0.0420(11) Uani 1 1 d . . . . .
H48A H 0.1341 0.4226 0.7685 0.050 Uiso 1 1 calc R U . . .
H48B H 0.2062 0.4110 0.7808 0.050 Uiso 1 1 calc R U . . .
C49 C 0.1454(3) 0.5015(3) 0.9394(4) 0.0476(13) Uani 1 1 d . . . . .
H49A H 0.1549 0.5106 1.0239 0.057 Uiso 1 1 calc R U . . .
H49B H 0.1031 0.4834 0.9143 0.057 Uiso 1 1 calc R U . . .
C50 C 0.1487(3) 0.5636(3) 0.8746(4) 0.0429(12) Uani 1 1 d . . . . .
H50A H 0.1186 0.5954 0.8900 0.051 Uiso 1 1 calc R U . . .
H50B H 0.1905 0.5827 0.9020 0.051 Uiso 1 1 calc R U . . .
C51 C 0.4976(2) 0.5613(3) 1.0463(4) 0.0392(10) Uani 1 1 d . . . . .
H51A H 0.4770 0.5936 1.0852 0.047 Uiso 1 1 calc R U . . .
H51B H 0.5365 0.5809 1.0381 0.047 Uiso 1 1 calc R U . . .
C52 C 0.4881(2) 0.4986(3) 0.8801(4) 0.0411(11) Uani 1 1 d . . . . .
H52A H 0.5267 0.5164 0.8672 0.049 Uiso 1 1 calc R U . . .
H52B H 0.4603 0.4871 0.8034 0.049 Uiso 1 1 calc R U . . .
C53 C 0.0036(2) 0.5614(3) 0.5515(4) 0.0404(11) Uani 1 1 d . . . . .
H53A H -0.0364 0.5812 0.5107 0.048 Uiso 1 1 calc R U . . .
H53B H 0.0262 0.5929 0.6102 0.048 Uiso 1 1 calc R U . . .
C54 C 0.0078(2) 0.4997(3) 0.3886(4) 0.0397(11) Uani 1 1 d . . . . .
H54A H 0.0338 0.4894 0.3354 0.048 Uiso 1 1 calc R U . . .
H54B H -0.0321 0.5170 0.3413 0.048 Uiso 1 1 calc R U . . .
N1 N 0.1676(2) 0.8446(2) 0.1026(4) 0.0438(10) Uani 1 1 d . . . . .
H1A H 0.153(3) 0.875(3) 0.135(5) 0.053 Uiso 1 1 d . U . . .
H1B H 0.184(3) 0.851(3) 0.035(5) 0.053 Uiso 1 1 d . U . . .
N2 N 0.1609(2) 0.1558(2) 0.5572(4) 0.0448(10) Uani 1 1 d . . . . .
H2A H 0.1456 0.1487 0.6170 0.054 Uiso 1 1 calc R U . . .
H2B H 0.1739 0.1230 0.5224 0.054 Uiso 1 1 calc R U . . .
N3 N 0.3441(2) 0.3429(2) 0.3940(4) 0.0445(10) Uani 1 1 d . . . . .
H3A H 0.3318 0.3760 0.3467 0.053 Uiso 1 1 calc R U . . .
H3B H 0.3604 0.3498 0.4687 0.053 Uiso 1 1 calc R U . . .
N4 N 0.6699(2) 0.1538(2) 0.5591(4) 0.0440(10) Uani 1 1 d . . . . .
H4A H 0.6859 0.1449 0.6331 0.053 Uiso 1 1 calc R U . . .
H4B H 0.6539 0.1224 0.5102 0.053 Uiso 1 1 calc R U . . .
N5 N 0.0070(2) 0.1542(2) 0.2221(4) 0.0457(10) Uani 1 1 d . . . . .
H5C H 0.014(3) 0.150(3) 0.294(6) 0.055 Uiso 1 1 d . U . . .
H5B H -0.021(3) 0.131(3) 0.178(5) 0.055 Uiso 1 1 d . U . . .
N6 N 0.4984(2) 0.3465(2) 0.2150(4) 0.0448(10) Uani 1 1 d . . . . .
H6A H 0.4814 0.3562 0.2715 0.054 Uiso 1 1 calc R U . . .
H6B H 0.5155 0.3773 0.1825 0.054 Uiso 1 1 calc R U . . .
O1 O 0.18989(17) 0.54187(16) 0.2277(3) 0.0408(8) Uani 1 1 d . . . . .
O2 O 0.14793(17) 0.58046(17) 0.3643(3) 0.0402(8) Uani 1 1 d . . . . .
H2 H 0.1519 0.5414 0.3863 0.060 Uiso 1 1 calc R U . . .
O4 O 0.19400(18) 0.41884(16) 0.3031(3) 0.0413(8) Uani 1 1 d . . . . .
H4C H 0.1935 0.4584 0.2849 0.062 Uiso 1 1 calc R U . . .
O3 O 0.15724(17) 0.46006(16) 0.4445(3) 0.0389(8) Uani 1 1 d . . . . .
O6 O 0.30466(18) 0.07868(17) 0.1062(3) 0.0429(8) Uani 1 1 d . . . . .
H6C H 0.3029 0.0387 0.0904 0.064 Uiso 1 1 calc R U . . .
O5 O 0.33874(18) 0.03939(16) 0.2873(3) 0.0420(8) Uani 1 1 d . . . . .
O7 O 0.69797(18) 0.45593(17) 0.4608(3) 0.0439(8) Uani 1 1 d . . . . .
O8 O 0.65526(19) 0.41933(17) 0.2814(3) 0.0443(8) Uani 1 1 d . . . . .
H8 H 0.6540 0.4594 0.2666 0.066 Uiso 1 1 calc R U . . .
O9 O -0.01879(18) 0.42281(18) -0.0530(3) 0.0455(9) Uani 1 1 d . . . . .
O10 O 0.02793(19) 0.45623(18) 0.1263(3) 0.0474(9) Uani 1 1 d . . . . .
H10A H 0.0259 0.4919 0.0910 0.071 Uiso 1 1 calc R U . . .
O11 O 0.51980(19) 0.07665(18) -0.0350(3) 0.0480(9) Uani 1 1 d . . . . .
O12 O 0.47120(19) 0.04479(18) 0.0972(3) 0.0483(9) Uani 1 1 d . . . . .
H12 H 0.4732 0.0088 0.0649 0.072 Uiso 1 1 calc R U . . .
O13 O 0.37059(15) 0.55225(16) 0.1311(3) 0.0367(7) Uani 1 1 d . . . . .
O14 O 0.31361(18) 0.45389(18) 0.2315(3) 0.0490(9) Uani 1 1 d . . . . .
O15 O 0.18871(16) 0.45489(17) 0.9175(3) 0.0424(8) Uani 1 1 d . . . . .
O16 O 0.13528(16) 0.55104(17) 0.7527(3) 0.0413(8) Uani 1 1 d . . . . .
O17 O 0.45901(16) 0.54729(17) 0.9350(3) 0.0418(8) Uani 1 1 d . . . . .
O18 O 0.03815(17) 0.54885(19) 0.4706(3) 0.0473(9) Uani 1 1 d . . . . .


_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
C1 O1 1.233(5) . ?
C1 O2 1.305(5) . ?
C1 C2 1.474(6) . ?
C2 C7 1.392(6) . ?
C2 C3 1.399(6) . ?
C3 C4 1.378(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(6) . ?
C4 H4 0.9500 . ?
C5 N1 1.369(6) . ?
C5 C6 1.412(6) . ?
C6 C7 1.381(7) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 O3 1.244(5) . ?
C8 O4 1.305(5) . ?
C8 C9 1.461(6) . ?
C9 C10 1.397(6) . ?
C9 C14 1.396(6) . ?
C10 C11 1.380(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.403(6) . ?
C11 H11 0.9500 . ?
C12 N2 1.364(6) . ?
C12 C13 1.401(6) . ?
C13 C14 1.382(7) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 O5 1.257(5) . ?
C15 O6 1.299(5) . ?
C15 C16 1.463(6) . ?
C16 C21 1.399(6) . ?
C16 C17 1.401(6) . ?
C17 C18 1.372(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.405(6) . ?
C18 H18 0.9500 . ?
C19 N3 1.363(6) . ?
C19 C20 1.411(7) . ?
C20 C21 1.373(7) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O7 1.245(5) . ?
C22 O8 1.305(5) . ?
C22 C23 1.464(6) . ?
C23 C24 1.393(6) . ?
C23 C28 1.404(6) . ?
C24 C25 1.374(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.398(6) . ?
C25 H25 0.9500 . ?
C26 N4 1.369(6) . ?
C26 C27 1.405(6) . ?
C27 C28 1.367(6) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 O9 1.266(5) . ?
C29 O10 1.278(6) . ?
C29 C30 1.466(7) . ?
C30 C31 1.400(6) . ?
C30 C35 1.398(6) . ?
C31 C32 1.370(7) . ?
C31 H31 0.9500 . ?
C32 C33 1.404(7) . ?
C32 H32 0.9500 . ?
C33 N5 1.372(7) . ?
C33 C34 1.401(6) . ?
C34 C35 1.378(7) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 O11 1.268(5) . ?
C36 O12 1.285(5) . ?
C36 C37 1.465(6) . ?
C37 C42 1.400(6) . ?
C37 C38 1.405(6) . ?
C38 C39 1.380(7) . ?
C38 H38 0.9500 . ?
C39 C40 1.388(7) . ?
C39 H39 0.9500 . ?
C40 N6 1.372(6) . ?
C40 C41 1.414(6) . ?
C41 C42 1.380(6) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 O14 1.414(6) . ?
C43 C44 1.500(7) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 O13 1.422(6) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 O13 1.420(5) . ?
C45 C46 1.501(7) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 O14 1.424(7) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 O16 1.429(6) . ?
C47 C48 1.504(7) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 O15 1.423(6) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 O15 1.436(6) . ?
C49 C50 1.503(7) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 O16 1.426(6) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 O17 1.409(6) . ?
C51 C52 1.495(7) 3_667 ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 O17 1.441(6) . ?
C52 C51 1.496(7) 3_667 ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 O18 1.409(6) . ?
C53 C54 1.497(7) 3_566 ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 O18 1.444(6) . ?
C54 C53 1.497(7) 3_566 ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
N1 H1A 0.84(6) . ?
N1 H1B 0.98(6) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N5 H5C 0.83(6) . ?
N5 H5B 0.86(6) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
O2 H2 0.8400 . ?
O4 H4C 0.8400 . ?
O6 H6C 0.8400 . ?
O8 H8 0.8400 . ?
O10 H10A 0.8400 . ?
O12 H12 0.8400 . ?

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
O1 C1 O2 122.7(4) . . ?
O1 C1 C2 121.8(4) . . ?
O2 C1 C2 115.5(4) . . ?
C7 C2 C3 118.6(4) . . ?
C7 C2 C1 120.1(4) . . ?
C3 C2 C1 121.3(4) . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 120.6(4) . . ?
N1 C5 C6 120.5(4) . . ?
C4 C5 C6 118.8(4) . . ?
C7 C6 C5 120.0(4) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 121.2(4) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
O3 C8 O4 121.8(4) . . ?
O3 C8 C9 122.3(4) . . ?
O4 C8 C9 115.9(4) . . ?
C10 C9 C14 118.4(4) . . ?
C10 C9 C8 121.5(4) . . ?
C14 C9 C8 120.1(4) . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.7(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
N2 C12 C13 120.9(4) . . ?
N2 C12 C11 120.8(4) . . ?
C13 C12 C11 118.3(4) . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C9 120.9(4) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
O5 C15 O6 122.5(4) . . ?
O5 C15 C16 120.0(4) . . ?
O6 C15 C16 117.4(4) . . ?
C21 C16 C17 118.2(4) . . ?
C21 C16 C15 120.3(4) . . ?
C17 C16 C15 121.5(4) . . ?
C18 C17 C16 120.3(4) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 121.6(4) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
N3 C19 C18 121.2(4) . . ?
N3 C19 C20 120.7(4) . . ?
C18 C19 C20 118.1(4) . . ?
C21 C20 C19 119.8(4) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C16 122.0(4) . . ?
C20 C21 H21 119.0 . . ?
C16 C21 H21 119.0 . . ?
O7 C22 O8 122.0(4) . . ?
O7 C22 C23 121.4(4) . . ?
O8 C22 C23 116.5(4) . . ?
C24 C23 C28 118.2(4) . . ?
C24 C23 C22 120.5(4) . . ?
C28 C23 C22 121.4(4) . . ?
C25 C24 C23 121.6(4) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C24 C25 C26 120.4(4) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
N4 C26 C25 121.4(4) . . ?
N4 C26 C27 120.6(4) . . ?
C25 C26 C27 118.0(4) . . ?
C28 C27 C26 121.5(4) . . ?
C28 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C27 C28 C23 120.4(4) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?
O9 C29 O10 122.2(5) . . ?
O9 C29 C30 119.8(4) . . ?
O10 C29 C30 118.0(4) . . ?
C31 C30 C35 118.4(4) . . ?
C31 C30 C29 120.8(4) . . ?
C35 C30 C29 120.8(4) . . ?
C32 C31 C30 121.2(4) . . ?
C32 C31 H31 119.4 . . ?
C30 C31 H31 119.4 . . ?
C31 C32 C33 120.3(4) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
N5 C33 C34 119.8(5) . . ?
N5 C33 C32 121.4(5) . . ?
C34 C33 C32 118.8(5) . . ?
C35 C34 C33 120.4(5) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C30 120.8(4) . . ?
C34 C35 H35 119.6 . . ?
C30 C35 H35 119.6 . . ?
O11 C36 O12 122.1(4) . . ?
O11 C36 C37 120.0(4) . . ?
O12 C36 C37 117.9(4) . . ?
C42 C37 C38 119.2(4) . . ?
C42 C37 C36 120.2(4) . . ?
C38 C37 C36 120.6(4) . . ?
C39 C38 C37 120.6(4) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C38 C39 C40 120.8(4) . . ?
C38 C39 H39 119.6 . . ?
C40 C39 H39 119.6 . . ?
N6 C40 C39 121.9(4) . . ?
N6 C40 C41 119.4(4) . . ?
C39 C40 C41 118.7(4) . . ?
C42 C41 C40 120.9(4) . . ?
C42 C41 H41 119.5 . . ?
C40 C41 H41 119.5 . . ?
C41 C42 C37 119.9(4) . . ?
C41 C42 H42 120.1 . . ?
C37 C42 H42 120.1 . . ?
O14 C43 C44 111.0(4) . . ?
O14 C43 H43A 109.4 . . ?
C44 C43 H43A 109.4 . . ?
O14 C43 H43B 109.4 . . ?
C44 C43 H43B 109.4 . . ?
H43A C43 H43B 108.0 . . ?
O13 C44 C43 111.4(4) . . ?
O13 C44 H44A 109.4 . . ?
C43 C44 H44A 109.4 . . ?
O13 C44 H44B 109.4 . . ?
C43 C44 H44B 109.4 . . ?
H44A C44 H44B 108.0 . . ?
O13 C45 C46 110.3(4) . . ?
O13 C45 H45A 109.6 . . ?
C46 C45 H45A 109.6 . . ?
O13 C45 H45B 109.6 . . ?
C46 C45 H45B 109.6 . . ?
H45A C45 H45B 108.1 . . ?
O14 C46 C45 111.1(5) . . ?
O14 C46 H46A 109.4 . . ?
C45 C46 H46A 109.4 . . ?
O14 C46 H46B 109.4 . . ?
C45 C46 H46B 109.4 . . ?
H46A C46 H46B 108.0 . . ?
O16 C47 C48 110.7(4) . . ?
O16 C47 H47A 109.5 . . ?
C48 C47 H47A 109.5 . . ?
O16 C47 H47B 109.5 . . ?
C48 C47 H47B 109.5 . . ?
H47A C47 H47B 108.1 . . ?
O15 C48 C47 110.4(4) . . ?
O15 C48 H48A 109.6 . . ?
C47 C48 H48A 109.6 . . ?
O15 C48 H48B 109.6 . . ?
C47 C48 H48B 109.6 . . ?
H48A C48 H48B 108.1 . . ?
O15 C49 C50 110.2(4) . . ?
O15 C49 H49A 109.6 . . ?
C50 C49 H49A 109.6 . . ?
O15 C49 H49B 109.6 . . ?
C50 C49 H49B 109.6 . . ?
H49A C49 H49B 108.1 . . ?
O16 C50 C49 110.1(4) . . ?
O16 C50 H50A 109.6 . . ?
C49 C50 H50A 109.6 . . ?
O16 C50 H50B 109.6 . . ?
C49 C50 H50B 109.6 . . ?
H50A C50 H50B 108.2 . . ?
O17 C51 C52 111.6(4) . 3_667 ?
O17 C51 H51A 109.3 . . ?
C52 C51 H51A 109.3 3_667 . ?
O17 C51 H51B 109.3 . . ?
C52 C51 H51B 109.3 3_667 . ?
H51A C51 H51B 108.0 . . ?
O17 C52 C51 111.1(4) . 3_667 ?
O17 C52 H52A 109.4 . . ?
C51 C52 H52A 109.4 3_667 . ?
O17 C52 H52B 109.4 . . ?
C51 C52 H52B 109.4 3_667 . ?
H52A C52 H52B 108.0 . . ?
O18 C53 C54 111.5(4) . 3_566 ?
O18 C53 H53A 109.3 . . ?
C54 C53 H53A 109.3 3_566 . ?
O18 C53 H53B 109.3 . . ?
C54 C53 H53B 109.3 3_566 . ?
H53A C53 H53B 108.0 . . ?
O18 C54 C53 111.9(4) . 3_566 ?
O18 C54 H54A 109.2 . . ?
C53 C54 H54A 109.2 3_566 . ?
O18 C54 H54B 109.2 . . ?
C53 C54 H54B 109.2 3_566 . ?
H54A C54 H54B 107.9 . . ?
C5 N1 H1A 120(4) . . ?
C5 N1 H1B 117(4) . . ?
H1A N1 H1B 123(5) . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C19 N3 H3A 120.0 . . ?
C19 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C26 N4 H4A 120.0 . . ?
C26 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C33 N5 H5C 116(5) . . ?
C33 N5 H5B 112(4) . . ?
H5C N5 H5B 118(6) . . ?
C40 N6 H6A 120.0 . . ?
C40 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C1 O2 H2 109.5 . . ?
C8 O4 H4C 109.5 . . ?
C15 O6 H6C 109.5 . . ?
C22 O8 H8 109.5 . . ?
C29 O10 H10A 109.5 . . ?
C36 O12 H12 109.5 . . ?
C45 O13 C44 110.2(4) . . ?
C43 O14 C46 110.0(4) . . ?
C48 O15 C49 109.7(4) . . ?
C47 O16 C50 109.8(4) . . ?
C51 O17 C52 109.2(4) . . ?
C53 O18 C54 110.1(4) . . ?

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
O1 C1 C2 C7 -2.1(7) . . . . ?
O2 C1 C2 C7 176.9(4) . . . . ?
O1 C1 C2 C3 179.2(4) . . . . ?
O2 C1 C2 C3 -1.7(6) . . . . ?
C7 C2 C3 C4 0.2(6) . . . . ?
C1 C2 C3 C4 178.9(4) . . . . ?
C2 C3 C4 C5 -1.1(7) . . . . ?
C3 C4 C5 N1 -178.5(4) . . . . ?
C3 C4 C5 C6 1.4(6) . . . . ?
N1 C5 C6 C7 179.1(4) . . . . ?
C4 C5 C6 C7 -0.9(7) . . . . ?
C5 C6 C7 C2 0.0(7) . . . . ?
C3 C2 C7 C6 0.3(6) . . . . ?
C1 C2 C7 C6 -178.4(4) . . . . ?
O3 C8 C9 C10 -178.3(4) . . . . ?
O4 C8 C9 C10 2.7(6) . . . . ?
O3 C8 C9 C14 2.6(7) . . . . ?
O4 C8 C9 C14 -176.5(4) . . . . ?
C14 C9 C10 C11 0.0(6) . . . . ?
C8 C9 C10 C11 -179.1(4) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C10 C11 C12 N2 179.6(4) . . . . ?
C10 C11 C12 C13 -0.7(6) . . . . ?
N2 C12 C13 C14 -179.8(4) . . . . ?
C11 C12 C13 C14 0.5(7) . . . . ?
C12 C13 C14 C9 0.0(7) . . . . ?
C10 C9 C14 C13 -0.2(6) . . . . ?
C8 C9 C14 C13 178.9(4) . . . . ?
O5 C15 C16 C21 6.1(6) . . . . ?
O6 C15 C16 C21 -175.0(4) . . . . ?
O5 C15 C16 C17 -175.5(4) . . . . ?
O6 C15 C16 C17 3.4(6) . . . . ?
C21 C16 C17 C18 0.4(6) . . . . ?
C15 C16 C17 C18 -178.0(4) . . . . ?
C16 C17 C18 C19 0.7(6) . . . . ?
C17 C18 C19 N3 178.4(4) . . . . ?
C17 C18 C19 C20 -1.4(6) . . . . ?
N3 C19 C20 C21 -178.7(4) . . . . ?
C18 C19 C20 C21 1.1(6) . . . . ?
C19 C20 C21 C16 -0.1(6) . . . . ?
C17 C16 C21 C20 -0.6(6) . . . . ?
C15 C16 C21 C20 177.8(4) . . . . ?
O7 C22 C23 C24 -2.2(7) . . . . ?
O8 C22 C23 C24 177.4(4) . . . . ?
O7 C22 C23 C28 179.4(4) . . . . ?
O8 C22 C23 C28 -1.0(6) . . . . ?
C28 C23 C24 C25 0.1(6) . . . . ?
C22 C23 C24 C25 -178.4(4) . . . . ?
C23 C24 C25 C26 0.0(6) . . . . ?
C24 C25 C26 N4 177.9(4) . . . . ?
C24 C25 C26 C27 -0.8(6) . . . . ?
N4 C26 C27 C28 -177.1(4) . . . . ?
C25 C26 C27 C28 1.6(6) . . . . ?
C26 C27 C28 C23 -1.5(7) . . . . ?
C24 C23 C28 C27 0.7(6) . . . . ?
C22 C23 C28 C27 179.1(4) . . . . ?
O9 C29 C30 C31 -179.8(4) . . . . ?
O10 C29 C30 C31 -0.6(6) . . . . ?
O9 C29 C30 C35 -0.7(7) . . . . ?
O10 C29 C30 C35 178.6(4) . . . . ?
C35 C30 C31 C32 1.2(6) . . . . ?
C29 C30 C31 C32 -179.6(4) . . . . ?
C30 C31 C32 C33 0.1(6) . . . . ?
C31 C32 C33 N5 177.4(4) . . . . ?
C31 C32 C33 C34 -0.8(6) . . . . ?
N5 C33 C34 C35 -178.0(4) . . . . ?
C32 C33 C34 C35 0.3(6) . . . . ?
C33 C34 C35 C30 1.0(7) . . . . ?
C31 C30 C35 C34 -1.8(6) . . . . ?
C29 C30 C35 C34 179.0(4) . . . . ?
O11 C36 C37 C42 -0.8(7) . . . . ?
O12 C36 C37 C42 178.8(4) . . . . ?
O11 C36 C37 C38 179.9(4) . . . . ?
O12 C36 C37 C38 -0.5(7) . . . . ?
C42 C37 C38 C39 0.5(7) . . . . ?
C36 C37 C38 C39 179.8(4) . . . . ?
C37 C38 C39 C40 0.6(7) . . . . ?
C38 C39 C40 N6 177.9(4) . . . . ?
C38 C39 C40 C41 -0.7(7) . . . . ?
N6 C40 C41 C42 -178.8(4) . . . . ?
C39 C40 C41 C42 -0.1(7) . . . . ?
C40 C41 C42 C37 1.2(7) . . . . ?
C38 C37 C42 C41 -1.4(7) . . . . ?
C36 C37 C42 C41 179.3(4) . . . . ?
O14 C43 C44 O13 56.5(6) . . . . ?
O13 C45 C46 O14 -58.0(6) . . . . ?
O16 C47 C48 O15 -58.0(6) . . . . ?
O15 C49 C50 O16 59.1(6) . . . . ?
C46 C45 O13 C44 56.9(6) . . . . ?
C43 C44 O13 C45 -56.5(6) . . . . ?
C44 C43 O14 C46 -56.3(6) . . . . ?
C45 C46 O14 C43 57.4(6) . . . . ?
C47 C48 O15 C49 57.8(6) . . . . ?
C50 C49 O15 C48 -58.6(6) . . . . ?
C48 C47 O16 C50 57.9(6) . . . . ?
C49 C50 O16 C47 -58.4(6) . . . . ?
C52 C51 O17 C52 -56.9(5) 3_667 . . . ?
C51 C52 O17 C51 56.5(6) 3_667 . . . ?
C54 C53 O18 C54 55.3(6) 3_566 . . . ?
C53 C54 O18 C53 -55.5(6) 3_566 . . . ?

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
C44 H44A O5 0.99 2.50 3.442(6) 158.6 4_565
C46 H46B O7 0.99 2.47 3.454(6) 172.0 3_666
C47 H47B O3 0.99 2.45 3.435(6) 170.9 .
C49 H49A O1 0.99 2.43 3.417(6) 172.1 1_556
C52 H52B O12 0.99 2.61 3.409(6) 137.3 4_566
C54 H54A O10 0.99 2.55 3.392(6) 142.6 .
N1 H1A O16 0.84(6) 2.17(6) 2.999(6) 166(6) 4_575
N1 H1B O2 0.98(6) 2.43(6) 3.155(5) 130(4) 4_575
N2 H2A O4 0.88 2.60 3.216(5) 128.0 4_566
N2 H2B O15 0.88 2.11 2.979(6) 169.5 4_565
N3 H3A O14 0.88 2.08 2.952(6) 172.9 .
N4 H4B O13 0.88 2.17 3.036(5) 167.1 2_645
N4 H4A O8 0.88 2.44 3.135(5) 135.9 4_566
N5 H5C O9 0.83(6) 2.60(6) 3.289(6) 140(6) 4_566
N5 H5B O2 0.86(6) 2.94(6) 3.682(6) 146(5) 2_545
N5 H5B O18 0.86(6) 2.39(7) 3.123(7) 143(5) 2_545
N6 H6A O11 0.88 2.63 3.291(6) 132.9 4_566
N6 H6B O17 0.88 2.26 3.123(6) 167.3 3_666
O2 H2 O3 0.84 1.80 2.639(5) 174.4 .
O4 H4C O1 0.84 1.84 2.675(5) 173.5 .
O6 H6C O7 0.84 1.80 2.640(5) 172.3 2_645
O8 H8 O5 0.84 1.79 2.612(5) 166.9 2_655
O10 H10A O9 0.84 1.80 2.622(5) 163.9 3_565
O12 H12 O11 0.84 1.81 2.624(5) 164.4 3_655

_refine_diff_density_max         0.625
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.073


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dioxane/Water'
####################################################################### 
# 
# 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_s4880r
_database_code_depnum_ccdc_archive 'CCDC 2009899'
loop_
_audit_author_name
_audit_author_address
'Sarah Wright'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2017-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        '4-amino-2,3,5,6-tetrafluorobenzoic acid'
_chemical_formula_moiety         'C7 H3 F4 N O2'
_chemical_formula_sum            'C7 H3 F4 N O2'
_chemical_formula_weight         209.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H6 F6 O6'
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'
F F 0.0171 0.0103 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.1957(2)
_cell_length_b                   14.9867(6)
_cell_length_c                   11.5145(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.566(4)
_cell_angle_gamma                90
_cell_volume                     717.73(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4187
_cell_measurement_temperature    100.12(10)
_cell_measurement_theta_max      26.3070
_cell_measurement_theta_min      2.2390
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.880
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.30c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.483
_exptl_crystal_size_min          0.119
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8394
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.345
_diffrn_reflns_theta_min         2.243
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.12(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00 -33.00   1.00    1.00    --    5.00 -12.00 -24.00   48
  2  ω    -28.00  -2.00   1.00    1.00    --    5.00 -12.00 -24.00   26
  3  ω      3.00  47.00   1.00    1.00    --    5.00 -12.00 -24.00   44
  4  ω    -26.00  94.00   1.00    1.00    --    5.00  57.00-180.00  120
  5  ω    -36.00  84.00   1.00    1.00    --   -5.70  57.00 -90.00  120
  6  ω      8.00  33.00   1.00    1.00    --   -5.70  76.00-150.00   25
  7  ω    -45.00 -13.00   1.00    1.00    --   -5.70  76.00-150.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0696133000
_diffrn_orient_matrix_UB_12      -0.0033135000
_diffrn_orient_matrix_UB_13      -0.0594206000
_diffrn_orient_matrix_UB_21      -0.1533078000
_diffrn_orient_matrix_UB_22      -0.0066865000
_diffrn_orient_matrix_UB_23      0.0181735000
_diffrn_orient_matrix_UB_31      -0.0268095000
_diffrn_orient_matrix_UB_32      0.0467350000
_diffrn_orient_matrix_UB_33      -0.0016010000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1306
_reflns_number_total             1458
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+0.1770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0871
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
F1 F 1.02682(17) 0.21762(4) 0.54756(6) 0.0173(2) Uani 1 1 d . . . . .
F3 F 0.06298(18) 0.20548(5) 0.18543(6) 0.0182(2) Uani 1 1 d . . . . .
F4 F 0.29630(18) 0.36283(4) 0.25538(6) 0.0191(2) Uani 1 1 d . . . . .
F2 F 0.76972(18) 0.06398(4) 0.47903(6) 0.0194(2) Uani 1 1 d . . . . .
O2 O 0.7011(2) 0.45915(6) 0.40065(8) 0.0225(2) Uani 1 1 d . . . . .
O1 O 1.0453(2) 0.38534(6) 0.52948(9) 0.0256(3) Uani 1 1 d . . . . .
N1 N 0.2945(3) 0.04923(7) 0.29237(10) 0.0206(3) Uani 1 1 d . . . . .
C1 C 0.7874(3) 0.21970(8) 0.45877(10) 0.0137(3) Uani 1 1 d . . . . .
C5 C 0.4289(3) 0.29097(7) 0.31204(10) 0.0135(3) Uani 1 1 d . . . . .
C6 C 0.6776(3) 0.30040(8) 0.40542(10) 0.0130(3) Uani 1 1 d . . . . .
C3 C 0.4139(3) 0.12975(8) 0.32829(10) 0.0143(3) Uani 1 1 d . . . . .
C2 C 0.6578(3) 0.13883(8) 0.42225(10) 0.0146(3) Uani 1 1 d . . . . .
C7 C 0.8068(3) 0.38893(8) 0.44416(10) 0.0146(3) Uani 1 1 d . . . . .
C4 C 0.3044(3) 0.20969(8) 0.27459(10) 0.0141(3) Uani 1 1 d . . . . .
H1A H 0.354(4) 0.0037(12) 0.3312(16) 0.036(5) Uiso 1 1 d . . . . .
H1 H 1.115(5) 0.4378(14) 0.5469(18) 0.049(5) Uiso 1 1 d . . . . .
H1B H 0.147(5) 0.0456(11) 0.2345(16) 0.032(4) Uiso 1 1 d . . . . .


_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
F1 C1 1.3360(14) . ?
F3 C4 1.3453(14) . ?
F4 C5 1.3414(13) . ?
F2 C2 1.3512(13) . ?
O2 C7 1.2234(15) . ?
O1 C7 1.3079(15) . ?
O1 H1 0.85(2) . ?
N1 C3 1.3504(15) . ?
N1 H1A 0.836(19) . ?
N1 H1B 0.848(19) . ?
C1 C6 1.4063(16) . ?
C1 C2 1.3716(16) . ?
C5 C6 1.4032(17) . ?
C5 C4 1.3725(16) . ?
C6 C7 1.4796(15) . ?
C3 C2 1.3945(17) . ?
C3 C4 1.3978(16) . ?

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 110.0(14) . . ?
C3 N1 H1A 119.6(12) . . ?
C3 N1 H1B 120.0(12) . . ?
H1A N1 H1B 120.1(17) . . ?
F1 C1 C6 121.63(10) . . ?
F1 C1 C2 116.22(10) . . ?
C2 C1 C6 122.15(11) . . ?
F4 C5 C6 120.72(10) . . ?
F4 C5 C4 116.32(10) . . ?
C4 C5 C6 122.96(10) . . ?
C1 C6 C7 123.60(11) . . ?
C5 C6 C1 114.58(10) . . ?
C5 C6 C7 121.81(10) . . ?
N1 C3 C2 121.97(11) . . ?
N1 C3 C4 122.91(11) . . ?
C2 C3 C4 115.12(10) . . ?
F2 C2 C1 119.13(10) . . ?
F2 C2 C3 117.85(10) . . ?
C1 C2 C3 123.02(11) . . ?
O2 C7 O1 122.90(10) . . ?
O2 C7 C6 123.32(11) . . ?
O1 C7 C6 113.78(10) . . ?
F3 C4 C5 119.91(10) . . ?
F3 C4 C3 117.90(10) . . ?
C5 C4 C3 122.16(11) . . ?

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
F1 C1 C6 C5 178.84(10) . . . . ?
F1 C1 C6 C7 -1.99(18) . . . . ?
F1 C1 C2 F2 2.03(17) . . . . ?
F1 C1 C2 C3 -177.86(10) . . . . ?
F4 C5 C6 C1 178.28(10) . . . . ?
F4 C5 C6 C7 -0.90(18) . . . . ?
F4 C5 C4 F3 0.14(17) . . . . ?
F4 C5 C4 C3 -178.04(10) . . . . ?
N1 C3 C2 F2 -1.28(18) . . . . ?
N1 C3 C2 C1 178.61(11) . . . . ?
N1 C3 C4 F3 1.94(18) . . . . ?
N1 C3 C4 C5 -179.84(11) . . . . ?
C1 C6 C7 O2 -176.80(12) . . . . ?
C1 C6 C7 O1 3.22(17) . . . . ?
C5 C6 C7 O2 2.30(19) . . . . ?
C5 C6 C7 O1 -177.68(11) . . . . ?
C6 C1 C2 F2 -178.54(10) . . . . ?
C6 C1 C2 C3 1.56(19) . . . . ?
C6 C5 C4 F3 179.13(10) . . . . ?
C6 C5 C4 C3 0.9(2) . . . . ?
C2 C1 C6 C5 -0.55(18) . . . . ?
C2 C1 C6 C7 178.61(11) . . . . ?
C2 C3 C4 F3 -178.20(10) . . . . ?
C2 C3 C4 C5 0.02(18) . . . . ?
C4 C5 C6 C1 -0.66(18) . . . . ?
C4 C5 C6 C7 -179.84(10) . . . . ?
C4 C3 C2 F2 178.86(10) . . . . ?
C4 C3 C2 C1 -1.25(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.980
_oxdiff_exptl_absorpt_empirical_full_min 0.499
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
####################################################################### 
# 
# 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_s4499ma
_database_code_depnum_ccdc_archive 'CCDC 2009900'
loop_
_audit_author_name
_audit_author_address
'Sarah Wright'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------# 

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'4-amino-2,3,5,6-tetrafluorobenzoic acid dioxane solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 F4 N O6'
_chemical_formula_weight         385.31

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.0886(2)
_cell_length_b                   18.8246(5)
_cell_length_c                   12.8623(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.882(2)
_cell_angle_gamma                90
_cell_volume                     1714.18(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4613
_cell_measurement_theta_min      4.17
_cell_measurement_theta_max      71.73

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.248
_shelx_estimated_absorpt_T_min   0.729
_shelx_estimated_absorpt_T_max   0.855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.761286
_exptl_absorpt_correction_T_max  0.855
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13651
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.166
_diffrn_reflns_theta_max         72.138
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3275
_reflns_number_gt                2790
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+0.3650P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3275
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.28507(16) 0.33803(7) 1.03650(10) 0.0212(2) Uani 1 1 d . . . . .
C2 C 0.26943(16) 0.41570(6) 1.01818(9) 0.0195(2) Uani 1 1 d . . . . .
C3 C 0.32466(17) 0.46377(7) 1.09719(9) 0.0206(2) Uani 1 1 d . . . . .
C4 C 0.31091(18) 0.53588(7) 1.08459(10) 0.0220(3) Uani 1 1 d . . . . .
C5 C 0.24011(17) 0.56736(6) 0.99207(10) 0.0207(2) Uani 1 1 d . . . . .
C6 C 0.18555(17) 0.51944(7) 0.91296(9) 0.0214(2) Uani 1 1 d . . . . .
C7 C 0.19950(17) 0.44735(6) 0.92538(9) 0.0206(2) Uani 1 1 d . . . . .
C8 C 0.3935(2) 0.39133(8) 0.43568(13) 0.0382(4) Uani 1 1 d . . . . .
H8A H 0.4136 0.3726 0.3652 0.046 Uiso 1 1 calc R U . . .
H8B H 0.5185 0.4019 0.4699 0.046 Uiso 1 1 calc R U . . .
C9 C 0.2773(3) 0.45832(8) 0.42737(12) 0.0400(4) Uani 1 1 d . . . . .
H9A H 0.3453 0.4944 0.3876 0.048 Uiso 1 1 calc R U . . .
H9B H 0.1557 0.4482 0.3891 0.048 Uiso 1 1 calc R U . . .
C10 C 0.1458(2) 0.43360(8) 0.58522(12) 0.0372(3) Uani 1 1 d . . . . .
H10A H 0.0221 0.4230 0.5494 0.045 Uiso 1 1 calc R U . . .
H10B H 0.1223 0.4525 0.6552 0.045 Uiso 1 1 calc R U . . .
C11 C 0.2606(2) 0.36629(8) 0.59591(12) 0.0373(3) Uani 1 1 d . . . . .
H11A H 0.3811 0.3762 0.6355 0.045 Uiso 1 1 calc R U . . .
H11B H 0.1903 0.3304 0.6348 0.045 Uiso 1 1 calc R U . . .
C12 C 0.0151(2) 0.72813(9) 0.71785(12) 0.0361(3) Uani 1 1 d . . . . .
H12A H -0.0364 0.7751 0.6964 0.043 Uiso 1 1 calc R U . . .
H12B H -0.0922 0.6950 0.7241 0.043 Uiso 1 1 calc R U . . .
C13 C 0.1423(2) 0.70110(8) 0.63647(12) 0.0333(3) Uani 1 1 d . . . . .
H13A H 0.1860 0.6526 0.6553 0.040 Uiso 1 1 calc R U . . .
H13B H 0.0707 0.6985 0.5685 0.040 Uiso 1 1 calc R U . . .
C14 C 0.4027(2) 0.75248(8) 0.72679(11) 0.0318(3) Uani 1 1 d . . . . .
H14A H 0.5113 0.7851 0.7208 0.038 Uiso 1 1 calc R U . . .
H14B H 0.4525 0.7053 0.7482 0.038 Uiso 1 1 calc R U . . .
C15 C 0.2763(2) 0.78007(8) 0.80811(11) 0.0317(3) Uani 1 1 d . . . . .
H15A H 0.3479 0.7827 0.8761 0.038 Uiso 1 1 calc R U . . .
H15B H 0.2330 0.8286 0.7891 0.038 Uiso 1 1 calc R U . . .
F4 F 0.13732(12) 0.40701(4) 0.84462(6) 0.03072(19) Uani 1 1 d . . . . .
F3 F 0.11442(12) 0.54645(4) 0.82179(6) 0.03011(19) Uani 1 1 d . . . . .
F2 F 0.37068(12) 0.57903(4) 1.16340(6) 0.03176(19) Uani 1 1 d . . . . .
F1 F 0.40035(12) 0.44047(4) 1.18847(6) 0.03073(19) Uani 1 1 d . . . . .
N1 N 0.22659(18) 0.63821(6) 0.98052(10) 0.0295(3) Uani 1 1 d . . . . .
O1 O 0.28964(15) 0.31178(5) 1.12199(7) 0.0315(2) Uani 1 1 d . . . . .
O2 O 0.29526(15) 0.30039(5) 0.94991(7) 0.0303(2) Uani 1 1 d . . . . .
H2 H 0.3023 0.2570 0.9648 0.045 Uiso 1 1 calc R U . . .
O3 O 0.29843(15) 0.33918(5) 0.49496(8) 0.0345(2) Uani 1 1 d . . . . .
O4 O 0.24233(16) 0.48549(5) 0.52757(8) 0.0376(3) Uani 1 1 d . . . . .
O5 O 0.11658(14) 0.73451(5) 0.81665(7) 0.0308(2) Uani 1 1 d . . . . .
O6 O 0.30191(14) 0.74661(5) 0.62768(7) 0.0294(2) Uani 1 1 d . . . . .
H1A H 0.259(2) 0.6660(10) 1.0299(13) 0.029(4) Uiso 1 1 d . . . . .
H1B H 0.184(3) 0.6559(10) 0.9244(16) 0.040(5) Uiso 1 1 d . . . . .


_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
C1 O1 1.2046(16) . ?
C1 O2 1.3251(16) . ?
C1 C2 1.4843(17) . ?
C2 C3 1.4016(17) . ?
C2 C7 1.4021(17) . ?
C3 F1 1.3399(14) . ?
C3 C4 1.3700(18) . ?
C4 F2 1.3503(14) . ?
C4 C5 1.3997(18) . ?
C5 N1 1.3448(17) . ?
C5 C6 1.3998(17) . ?
C6 F3 1.3522(14) . ?
C6 C7 1.3693(18) . ?
C7 F4 1.3431(14) . ?
C8 O3 1.4320(17) . ?
C8 C9 1.507(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O4 1.4199(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O4 1.4225(19) . ?
C10 C11 1.508(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O3 1.4330(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O5 1.4335(17) . ?
C12 C13 1.504(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O6 1.4283(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O6 1.4339(17) . ?
C14 C15 1.504(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O5 1.4292(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
N1 H1A 0.846(18) . ?
N1 H1B 0.84(2) . ?
O2 H2 0.8400 . ?

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
O1 C1 O2 123.22(12) . . ?
O1 C1 C2 123.19(11) . . ?
O2 C1 C2 113.59(10) . . ?
C3 C2 C7 114.63(11) . . ?
C3 C2 C1 120.33(11) . . ?
C7 C2 C1 125.04(11) . . ?
F1 C3 C4 116.80(11) . . ?
F1 C3 C2 120.59(11) . . ?
C4 C3 C2 122.57(11) . . ?
F2 C4 C3 119.30(11) . . ?
F2 C4 C5 117.97(11) . . ?
C3 C4 C5 122.71(11) . . ?
N1 C5 C4 122.30(12) . . ?
N1 C5 C6 122.91(12) . . ?
C4 C5 C6 114.79(11) . . ?
F3 C6 C7 119.70(11) . . ?
F3 C6 C5 117.74(11) . . ?
C7 C6 C5 122.56(11) . . ?
F4 C7 C6 116.82(11) . . ?
F4 C7 C2 120.42(11) . . ?
C6 C7 C2 122.74(11) . . ?
O3 C8 C9 109.97(12) . . ?
O3 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
O3 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
O4 C9 C8 110.91(13) . . ?
O4 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
O4 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.0 . . ?
O4 C10 C11 110.67(13) . . ?
O4 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O3 C11 C10 109.95(12) . . ?
O3 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
O3 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
O5 C12 C13 110.72(12) . . ?
O5 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
O6 C13 C12 110.92(12) . . ?
O6 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
O6 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.0 . . ?
O6 C14 C15 110.93(12) . . ?
O6 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
O6 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
O5 C15 C14 110.39(12) . . ?
O5 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
O5 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C5 N1 H1A 121.0(12) . . ?
C5 N1 H1B 120.7(13) . . ?
H1A N1 H1B 118.3(18) . . ?
C1 O2 H2 109.5 . . ?
C8 O3 C11 110.67(11) . . ?
C9 O4 C10 109.65(11) . . ?
C15 O5 C12 110.26(10) . . ?
C13 O6 C14 109.72(10) . . ?

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
O1 C1 C2 C3 22.55(19) . . . . ?
O2 C1 C2 C3 -156.88(11) . . . . ?
O1 C1 C2 C7 -156.71(12) . . . . ?
O2 C1 C2 C7 23.87(17) . . . . ?
C7 C2 C3 F1 -177.56(11) . . . . ?
C1 C2 C3 F1 3.12(18) . . . . ?
C7 C2 C3 C4 0.12(18) . . . . ?
C1 C2 C3 C4 -179.21(11) . . . . ?
F1 C3 C4 F2 -0.82(17) . . . . ?
C2 C3 C4 F2 -178.58(11) . . . . ?
F1 C3 C4 C5 177.99(11) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
F2 C4 C5 N1 -1.39(19) . . . . ?
C3 C4 C5 N1 179.79(12) . . . . ?
F2 C4 C5 C6 178.38(11) . . . . ?
C3 C4 C5 C6 -0.44(18) . . . . ?
N1 C5 C6 F3 -0.77(19) . . . . ?
C4 C5 C6 F3 179.46(11) . . . . ?
N1 C5 C6 C7 -179.90(13) . . . . ?
C4 C5 C6 C7 0.33(18) . . . . ?
F3 C6 C7 F4 -1.01(17) . . . . ?
C5 C6 C7 F4 178.11(11) . . . . ?
F3 C6 C7 C2 -179.12(11) . . . . ?
C5 C6 C7 C2 0.00(19) . . . . ?
C3 C2 C7 F4 -178.28(11) . . . . ?
C1 C2 C7 F4 1.01(19) . . . . ?
C3 C2 C7 C6 -0.23(18) . . . . ?
C1 C2 C7 C6 179.06(12) . . . . ?
O3 C8 C9 O4 57.90(18) . . . . ?
O4 C10 C11 O3 -58.06(17) . . . . ?
O5 C12 C13 O6 -57.40(16) . . . . ?
O6 C14 C15 O5 58.01(15) . . . . ?
C9 C8 O3 C11 -56.85(17) . . . . ?
C10 C11 O3 C8 57.01(17) . . . . ?
C8 C9 O4 C10 -58.75(17) . . . . ?
C11 C10 O4 C9 58.78(17) . . . . ?
C14 C15 O5 C12 -57.20(15) . . . . ?
C13 C12 O5 C15 56.99(16) . . . . ?
C12 C13 O6 C14 57.24(15) . . . . ?
C15 C14 O6 C13 -57.65(15) . . . . ?

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
C8 H8A F1 0.99 2.61 3.3143(18) 128.6 1_554
C10 H10B F4 0.99 2.58 3.3774(17) 137.6 .
C12 H12A F4 0.99 2.63 3.6146(18) 172.4 2_556
C12 H12A O2 0.99 2.61 3.2969(17) 126.9 2_556
C12 H12B O1 0.99 2.48 3.1500(18) 124.3 3_567
C14 H14B O1 0.99 2.43 3.0944(17) 123.7 3_667
C15 H15B F2 0.99 2.60 3.3275(16) 130.5 4_575
O2 H2 O3 0.84 1.85 2.6903(13) 175.7 4_566
N1 H1A O6 0.846(18) 2.084(19) 2.9100(15) 165.3(16) 4_576
N1 H1B O5 0.84(2) 2.07(2) 2.8587(15) 157.6(18) .

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dioxane/Water'
####################################################################### 
# 
# 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_s5120l
_database_code_depnum_ccdc_archive 'CCDC 2009901'
loop_
_audit_author_name
_audit_author_address
'Sarah Wright'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2018-02-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        '4-amino-3-methylbenzoic acid'
_chemical_formula_moiety         '2(C8 H9 N O2)'
_chemical_formula_sum            'C16 H18 N2 O4'
_chemical_formula_weight         302.32
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.7033(4)
_cell_length_b                   8.7280(3)
_cell_length_c                   16.1405(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.802(4)
_cell_angle_gamma                90
_cell_volume                     1500.10(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4590
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      27.7390
_cell_measurement_theta_min      1.8820
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.30c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18127
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.001
_diffrn_reflns_theta_min         1.912
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 -38.00   1.00    1.00    --   19.70  35.00 174.00   27
  2  ω    -43.00 -16.00   1.00    1.00    --   19.70  60.00   0.00   27
  3  ω     10.00 109.00   1.00    1.00    --   19.70  60.00   0.00   99
  4  ω    -69.00 109.00   1.00    1.00    --   19.70  60.00-120.00  178
  5  ω    -45.00 109.00   1.00    1.00    --   19.70  14.00  60.00  154
  6  ω    -62.00  76.00   1.00    1.00    --   19.70  60.00 -90.00  138
  7  ω     28.00  58.00   1.00    1.00    --   19.70  60.00  30.00   30
  8  ω     79.00 104.00   1.00    1.00    --   19.70  60.00  30.00   25
  9  ω     -5.00  20.00   1.00    1.00    --   19.70  35.00 174.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0664492000
_diffrn_orient_matrix_UB_12      -0.0040210000
_diffrn_orient_matrix_UB_13      -0.0070922000
_diffrn_orient_matrix_UB_21      -0.0014128000
_diffrn_orient_matrix_UB_22      -0.0464417000
_diffrn_orient_matrix_UB_23      0.0359759000
_diffrn_orient_matrix_UB_31      -0.0048760000
_diffrn_orient_matrix_UB_32      0.0665612000
_diffrn_orient_matrix_UB_33      0.0246043000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2552
_reflns_number_total             3603
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3603
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.035
_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)+(0.0622P)²+0.2535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1437
_refine_special_details          ?
_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 C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O2(H2), N1(H1A,H1B), O4(H4), N2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C11(H11), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
;
_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 0.48857(10) 0.73070(13) 0.48067(7) 0.0359(3) Uani 1 1 d . . . . .
H2 H 0.5359 0.6735 0.4584 0.054 Uiso 1 1 d R . . . .
O1 O 0.64214(10) 0.71317(13) 0.58504(7) 0.0336(3) Uani 1 1 d . . . . .
N1 N 0.23845(12) 1.13616(15) 0.74056(8) 0.0326(3) Uani 1 1 d . . . . .
H1A H 0.1740 1.1880 0.7156 0.039 Uiso 1 1 d R . . . .
H1B H 0.2695 1.1660 0.7874 0.039 Uiso 1 1 d R . . . .
C2 C 0.46172(13) 0.86461(17) 0.60295(9) 0.0265(3) Uani 1 1 d . . . . .
C3 C 0.34939(14) 0.92786(17) 0.56599(9) 0.0275(3) Uani 1 1 d . . . . .
H3 H 0.3241 0.9065 0.5091 0.033 Uiso 1 1 calc R . . . .
C4 C 0.27435(14) 1.02014(17) 0.60949(9) 0.0266(3) Uani 1 1 d . . . . .
C5 C 0.31250(13) 1.05126(17) 0.69399(9) 0.0261(3) Uani 1 1 d . . . . .
C6 C 0.42514(14) 0.98916(18) 0.73115(10) 0.0289(3) Uani 1 1 d . . . . .
H6 H 0.4513 1.0107 0.7880 0.035 Uiso 1 1 calc R . . . .
C7 C 0.49812(14) 0.89758(18) 0.68652(10) 0.0285(3) Uani 1 1 d . . . . .
H7 H 0.5742 0.8562 0.7127 0.034 Uiso 1 1 calc R . . . .
C1 C 0.53806(14) 0.76404(18) 0.55625(9) 0.0284(3) Uani 1 1 d . . . . .
C8 C 0.15343(15) 1.08589(19) 0.56857(10) 0.0340(4) Uani 1 1 d . . . . .
H8A H 0.1593 1.1979 0.5677 0.051 Uiso 1 1 calc GR . . . .
H8B H 0.0838 1.0552 0.6000 0.051 Uiso 1 1 calc GR . . . .
H8C H 0.1385 1.0473 0.5114 0.051 Uiso 1 1 calc GR . . . .
O3 O 0.63029(10) 0.54907(14) 0.40210(7) 0.0374(3) Uani 1 1 d . . . . .
O4 O 0.78366(10) 0.52714(13) 0.50596(7) 0.0324(3) Uani 1 1 d . . . . .
H4 H 0.7368 0.5833 0.5293 0.049 Uiso 1 1 d R . . . .
N2 N 1.01386(13) 0.13263(15) 0.22768(9) 0.0372(4) Uani 1 1 d . . . . .
H2A H 0.9680 0.0851 0.1833 0.045 Uiso 1 1 d R . . . .
H2B H 1.0700 0.0721 0.2555 0.045 Uiso 1 1 d R . . . .
C10 C 0.80822(13) 0.40003(16) 0.37994(9) 0.0249(3) Uani 1 1 d . . . . .
C11 C 0.76098(13) 0.36631(16) 0.29831(9) 0.0264(3) Uani 1 1 d . . . . .
H11 H 0.6810 0.4055 0.2777 0.032 Uiso 1 1 calc R . . . .
C12 C 0.82665(14) 0.27769(17) 0.24640(10) 0.0277(3) Uani 1 1 d . . . . .
C13 C 0.94423(14) 0.21829(16) 0.27882(10) 0.0285(3) Uani 1 1 d . . . . .
C14 C 0.99255(14) 0.25372(17) 0.36002(10) 0.0304(4) Uani 1 1 d . . . . .
H14 H 1.0728 0.2158 0.3809 0.036 Uiso 1 1 calc R . . . .
C15 C 0.92580(14) 0.34290(17) 0.41055(10) 0.0282(3) Uani 1 1 d . . . . .
H15 H 0.9596 0.3654 0.4659 0.034 Uiso 1 1 calc R . . . .
C9 C 0.73290(14) 0.49727(17) 0.42968(9) 0.0266(3) Uani 1 1 d . . . . .
C16 C 0.77413(17) 0.2445(2) 0.15881(11) 0.0402(4) Uani 1 1 d . . . . .
H16A H 0.6936 0.2976 0.1469 0.060 Uiso 1 1 calc GR . . . .
H16B H 0.7613 0.1339 0.1519 0.060 Uiso 1 1 calc GR . . . .
H16C H 0.8330 0.2803 0.1203 0.060 Uiso 1 1 calc GR . . . .


_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 0.8195 . ?
O2 C1 1.3126(18) . ?
O1 C1 1.2447(18) . ?
N1 H1A 0.8872 . ?
N1 H1B 0.8358 . ?
N1 C5 1.3648(19) . ?
C2 C3 1.400(2) . ?
C2 C7 1.396(2) . ?
C2 C1 1.460(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(2) . ?
C4 C5 1.410(2) . ?
C4 C8 1.506(2) . ?
C5 C6 1.400(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.372(2) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O3 C9 1.2287(18) . ?
O4 H4 0.8198 . ?
O4 C9 1.3205(18) . ?
N2 H2A 0.9251 . ?
N2 H2B 0.8873 . ?
N2 C13 1.386(2) . ?
C10 C11 1.394(2) . ?
C10 C15 1.397(2) . ?
C10 C9 1.465(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(2) . ?
C12 C13 1.412(2) . ?
C12 C16 1.496(2) . ?
C13 C14 1.394(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(2) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C1 O2 H2 109.5 . . ?
H1A N1 H1B 118.1 . . ?
C5 N1 H1A 119.7 . . ?
C5 N1 H1B 117.9 . . ?
C3 C2 C1 121.23(13) . . ?
C7 C2 C3 118.30(14) . . ?
C7 C2 C1 120.46(13) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.19(14) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 118.59(14) . . ?
C3 C4 C8 121.22(14) . . ?
C5 C4 C8 120.19(14) . . ?
N1 C5 C4 120.65(13) . . ?
N1 C5 C6 119.80(14) . . ?
C6 C5 C4 119.50(14) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.79(14) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.64(14) . . ?
C6 C7 H7 119.7 . . ?
O2 C1 C2 114.76(13) . . ?
O1 C1 O2 121.99(14) . . ?
O1 C1 C2 123.25(14) . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 O4 H4 109.5 . . ?
H2A N2 H2B 113.8 . . ?
C13 N2 H2A 115.4 . . ?
C13 N2 H2B 113.4 . . ?
C11 C10 C15 119.13(14) . . ?
C11 C10 C9 118.24(13) . . ?
C15 C10 C9 122.63(13) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.18(14) . . ?
C12 C11 H11 118.9 . . ?
C11 C12 C13 117.99(14) . . ?
C11 C12 C16 121.02(14) . . ?
C13 C12 C16 120.99(14) . . ?
N2 C13 C12 119.36(15) . . ?
N2 C13 C14 120.59(14) . . ?
C14 C13 C12 119.93(14) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.09(14) . . ?
C15 C14 H14 119.5 . . ?
C10 C15 H15 120.2 . . ?
C14 C15 C10 119.65(14) . . ?
C14 C15 H15 120.2 . . ?
O3 C9 O4 122.25(14) . . ?
O3 C9 C10 122.41(14) . . ?
O4 C9 C10 115.34(13) . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
N1 C5 C6 C7 176.94(14) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 C3 C4 C8 -179.53(14) . . . . ?
C3 C2 C7 C6 0.3(2) . . . . ?
C3 C2 C1 O2 -4.5(2) . . . . ?
C3 C2 C1 O1 175.38(14) . . . . ?
C3 C4 C5 N1 -176.97(14) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C7 C2 C3 C4 -0.3(2) . . . . ?
C7 C2 C1 O2 174.15(14) . . . . ?
C7 C2 C1 O1 -5.9(2) . . . . ?
C1 C2 C3 C4 178.42(14) . . . . ?
C1 C2 C7 C6 -178.47(14) . . . . ?
C8 C4 C5 N1 2.5(2) . . . . ?
C8 C4 C5 C6 179.95(14) . . . . ?
N2 C13 C14 C15 177.93(14) . . . . ?
C10 C11 C12 C13 1.1(2) . . . . ?
C10 C11 C12 C16 -179.45(14) . . . . ?
C11 C10 C15 C14 -0.4(2) . . . . ?
C11 C10 C9 O3 0.3(2) . . . . ?
C11 C10 C9 O4 -178.90(13) . . . . ?
C11 C12 C13 N2 -178.23(13) . . . . ?
C11 C12 C13 C14 -2.1(2) . . . . ?
C12 C13 C14 C15 1.8(2) . . . . ?
C13 C14 C15 C10 -0.5(2) . . . . ?
C15 C10 C11 C12 0.1(2) . . . . ?
C15 C10 C9 O3 178.94(14) . . . . ?
C15 C10 C9 O4 -0.2(2) . . . . ?
C9 C10 C11 C12 178.84(13) . . . . ?
C9 C10 C15 C14 -179.10(13) . . . . ?
C16 C12 C13 N2 2.3(2) . . . . ?
C16 C12 C13 C14 178.51(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.735
_oxdiff_exptl_absorpt_empirical_full_min 0.328
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# 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_s5326r
_database_code_depnum_ccdc_archive 'CCDC 2009902'
loop_
_audit_author_name
_audit_author_address
'Sarah Wright'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2018-08-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        '4-amino-2-methylbenzoic acid'
_chemical_formula_moiety         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_chemical_absolute_configuration rm
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.74940(14)
_cell_length_b                   8.12614(16)
_cell_length_c                   22.7285(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1431.28(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5388
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.5250
_cell_measurement_theta_min      6.0180
_shelx_estimated_absorpt_T_max   0.910
_shelx_estimated_absorpt_T_min   0.842
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14d (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.114
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6832
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.829
_diffrn_reflns_theta_min         6.033
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  30.00   1.00    1.00    --  -45.00  56.00  89.00   84
  2  ω    -46.00  -5.00   1.00    1.00    --  -45.00 -76.00 177.00   41
  3  ω   -129.00 -51.00   1.00    1.00    --  -45.00 -76.00 177.00   78
  4  ω   -151.00-123.00   1.00    1.00    -- -110.00 -56.00 -53.00   28
  5  ω   -195.00-157.00   1.00    1.00    -- -110.00 -56.00 -53.00   38
  6  ω   -149.00-123.00   1.00    1.00    -- -110.00 -76.00 177.00   26
  7  ω     30.00  55.00   1.00    1.00    --    5.00  57.00-180.00   25
  8  ω   -113.00 -78.00   1.00    1.00    -- -110.00 -57.00-120.00   35
  9  ω   -199.00 -99.00   1.00    1.00    -- -110.00 -38.00-150.00  100
 10  ω   -198.00 -69.00   1.00    1.00    -- -110.00 -38.00-120.00  129
 11  ω   -101.00 -57.00   1.00    1.00    -- -110.00  56.00  89.00   44
 12  ω   -132.00 -25.00   1.00    1.00    -- -110.00  76.00 -56.00  107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1296739000
_diffrn_orient_matrix_UB_12      0.0784076000
_diffrn_orient_matrix_UB_13      0.0430198000
_diffrn_orient_matrix_UB_21      0.1308660000
_diffrn_orient_matrix_UB_22      0.1373054000
_diffrn_orient_matrix_UB_23      0.0138704000
_diffrn_orient_matrix_UB_31      -0.0746999000
_diffrn_orient_matrix_UB_32      0.1047294000
_diffrn_orient_matrix_UB_33      -0.0504729000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                2813
_reflns_number_total             2901
_reflns_odcompleteness_completeness 99.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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       'CrysAlisPro 1.171.40.14d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14d (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1138 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2901
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.058
_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)+(0.0418P)²+0.2167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0737
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.37851(18) 0.69442(16) 0.68360(5) 0.0304(3) Uani 1 1 d . . . . .
O2 O 0.41525(18) 0.49678(15) 0.61658(5) 0.0296(3) Uani 1 1 d . . . . .
O4 O 0.25695(19) 0.45528(15) 0.75176(5) 0.0330(3) Uani 1 1 d . . . . .
O3 O 0.3258(2) 0.25143(17) 0.69057(6) 0.0389(3) Uani 1 1 d . . . . .
N1 N 0.7238(2) 1.14969(19) 0.49152(7) 0.0290(3) Uani 1 1 d . . . . .
N2 N 0.0556(2) -0.2075(2) 0.89375(7) 0.0331(4) Uani 1 1 d . . . . .
C2 C 0.6091(2) 0.7322(2) 0.54371(7) 0.0233(3) Uani 1 1 d . . . . .
C5 C 0.5592(2) 1.0629(2) 0.57713(8) 0.0265(4) Uani 1 1 d . . . . .
C10 C 0.0971(2) 0.2098(2) 0.83066(7) 0.0245(3) Uani 1 1 d . . . . .
C15 C 0.1998(2) 0.1767(2) 0.78079(7) 0.0249(4) Uani 1 1 d . . . . .
C4 C 0.6561(2) 1.0259(2) 0.52682(7) 0.0244(4) Uani 1 1 d . . . . .
C7 C 0.5115(2) 0.7703(2) 0.59456(7) 0.0236(3) Uani 1 1 d . . . . .
C8 C 0.4326(2) 0.6415(2) 0.63171(7) 0.0249(3) Uani 1 1 d . . . . .
C3 C 0.6786(2) 0.8607(2) 0.51160(7) 0.0243(3) Uani 1 1 d . . . . .
C16 C 0.2615(2) 0.3074(2) 0.74121(7) 0.0276(4) Uani 1 1 d . . . . .
C6 C 0.4900(2) 0.9363(2) 0.61015(8) 0.0260(4) Uani 1 1 d . . . . .
C12 C 0.0974(2) -0.0836(2) 0.85481(8) 0.0265(4) Uani 1 1 d . . . . .
C13 C 0.1994(3) -0.1151(2) 0.80539(8) 0.0297(4) Uani 1 1 d . . . . .
C11 C 0.0473(2) 0.0789(2) 0.86610(8) 0.0258(4) Uani 1 1 d . . . . .
C1 C 0.6474(2) 0.5601(2) 0.52266(8) 0.0274(4) Uani 1 1 d . . . . .
C9 C 0.0411(3) 0.3801(2) 0.84813(8) 0.0286(4) Uani 1 1 d . . . . .
C14 C 0.2485(3) 0.0128(2) 0.76959(7) 0.0290(4) Uani 1 1 d . . . . .
H13 H 0.233(3) -0.227(3) 0.7960(10) 0.032(5) Uiso 1 1 d . . . . .
H3 H 0.747(3) 0.836(2) 0.4782(9) 0.023(5) Uiso 1 1 d . . . . .
H1C H 0.748(3) 0.562(3) 0.4943(10) 0.035(6) Uiso 1 1 d . . . . .
H1D H 0.551(3) 0.512(3) 0.5002(10) 0.031(5) Uiso 1 1 d . . . . .
H5 H 0.541(3) 1.177(3) 0.5887(9) 0.026(5) Uiso 1 1 d . . . . .
H11 H -0.023(3) 0.097(3) 0.8989(11) 0.036(6) Uiso 1 1 d . . . . .
H1A H 0.804(4) 1.111(3) 0.4669(12) 0.046(7) Uiso 1 1 d . . . . .
H14 H 0.321(3) -0.003(3) 0.7356(11) 0.036(6) Uiso 1 1 d . . . . .
H6 H 0.423(3) 0.963(3) 0.6430(11) 0.034(6) Uiso 1 1 d . . . . .
H1E H 0.671(3) 0.483(3) 0.5557(10) 0.035(6) Uiso 1 1 d . . . . .
H2A H -0.035(3) -0.188(3) 0.9174(12) 0.046(7) Uiso 1 1 d . . . . .
H1B H 0.753(3) 1.238(4) 0.5114(12) 0.048(7) Uiso 1 1 d . . . . .
H2B H 0.060(3) -0.311(3) 0.8795(11) 0.040(6) Uiso 1 1 d . . . . .
H9A H -0.045(3) 0.376(3) 0.8811(12) 0.050(7) Uiso 1 1 d . . . . .
H1 H 0.330(4) 0.604(4) 0.7049(13) 0.056(8) Uiso 1 1 d . . . . .
H9B H 0.138(4) 0.447(3) 0.8612(12) 0.050(7) Uiso 1 1 d . . . . .
H9C H -0.008(3) 0.447(3) 0.8153(10) 0.036(6) Uiso 1 1 d . . . . .
H3A H 0.352(4) 0.348(4) 0.6670(14) 0.075(10) Uiso 1 1 d . . . . .


_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
O1 C8 1.323(2) . ?
O1 H1 0.95(3) . ?
O2 C8 1.233(2) . ?
O4 C16 1.226(2) . ?
O3 C16 1.334(2) . ?
O3 H3A 0.97(3) . ?
N1 C4 1.389(2) . ?
N1 H1A 0.89(3) . ?
N1 H1B 0.88(3) . ?
N2 C12 1.379(2) . ?
N2 H2A 0.90(3) . ?
N2 H2B 0.90(3) . ?
C2 C7 1.415(2) . ?
C2 C3 1.383(2) . ?
C2 C1 1.507(2) . ?
C5 C4 1.401(2) . ?
C5 C6 1.382(3) . ?
C5 H5 0.97(2) . ?
C10 C15 1.411(2) . ?
C10 C11 1.389(3) . ?
C10 C9 1.503(2) . ?
C15 C16 1.472(2) . ?
C15 C14 1.407(2) . ?
C4 C3 1.397(2) . ?
C7 C8 1.477(2) . ?
C7 C6 1.404(2) . ?
C3 H3 0.95(2) . ?
C6 H6 0.93(2) . ?
C12 C13 1.397(3) . ?
C12 C11 1.400(2) . ?
C13 C14 1.374(3) . ?
C13 H13 0.97(2) . ?
C11 H11 0.94(2) . ?
C1 H1C 1.01(2) . ?
C1 H1D 0.98(2) . ?
C1 H1E 0.99(2) . ?
C9 H9A 1.00(3) . ?
C9 H9B 0.98(3) . ?
C9 H9C 1.00(2) . ?
C14 H14 0.96(2) . ?

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
C8 O1 H1 109.1(17) . . ?
C16 O3 H3A 106.1(19) . . ?
C4 N1 H1A 111.7(17) . . ?
C4 N1 H1B 113.1(17) . . ?
H1A N1 H1B 115(2) . . ?
C12 N2 H2A 116.0(17) . . ?
C12 N2 H2B 116.2(16) . . ?
H2A N2 H2B 114(2) . . ?
C7 C2 C1 124.55(15) . . ?
C3 C2 C7 118.30(15) . . ?
C3 C2 C1 117.13(15) . . ?
C4 C5 H5 120.2(12) . . ?
C6 C5 C4 119.44(16) . . ?
C6 C5 H5 120.4(12) . . ?
C15 C10 C9 123.38(15) . . ?
C11 C10 C15 118.47(15) . . ?
C11 C10 C9 118.14(15) . . ?
C10 C15 C16 122.49(16) . . ?
C14 C15 C10 118.49(16) . . ?
C14 C15 C16 119.00(15) . . ?
N1 C4 C5 121.25(16) . . ?
N1 C4 C3 120.34(16) . . ?
C3 C4 C5 118.38(16) . . ?
C2 C7 C8 122.23(15) . . ?
C6 C7 C2 118.63(15) . . ?
C6 C7 C8 119.14(15) . . ?
O1 C8 C7 114.25(15) . . ?
O2 C8 O1 121.60(16) . . ?
O2 C8 C7 124.15(15) . . ?
C2 C3 C4 123.08(16) . . ?
C2 C3 H3 118.6(12) . . ?
C4 C3 H3 118.3(12) . . ?
O4 C16 O3 120.91(17) . . ?
O4 C16 C15 125.34(16) . . ?
O3 C16 C15 113.76(15) . . ?
C5 C6 C7 122.16(16) . . ?
C5 C6 H6 118.2(14) . . ?
C7 C6 H6 119.5(14) . . ?
N2 C12 C13 121.00(16) . . ?
N2 C12 C11 120.39(16) . . ?
C13 C12 C11 118.49(16) . . ?
C12 C13 H13 119.9(14) . . ?
C14 C13 C12 119.62(17) . . ?
C14 C13 H13 120.5(13) . . ?
C10 C11 C12 122.62(16) . . ?
C10 C11 H11 120.3(15) . . ?
C12 C11 H11 117.0(15) . . ?
C2 C1 H1C 110.0(13) . . ?
C2 C1 H1D 112.9(13) . . ?
C2 C1 H1E 112.2(13) . . ?
H1C C1 H1D 104.8(18) . . ?
H1C C1 H1E 110.5(19) . . ?
H1D C1 H1E 106.2(18) . . ?
C10 C9 H9A 111.1(16) . . ?
C10 C9 H9B 111.9(16) . . ?
C10 C9 H9C 114.7(14) . . ?
H9A C9 H9B 108(2) . . ?
H9A C9 H9C 109(2) . . ?
H9B C9 H9C 102(2) . . ?
C15 C14 H14 115.4(14) . . ?
C13 C14 C15 122.31(17) . . ?
C13 C14 H14 122.2(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.179
_oxdiff_exptl_absorpt_empirical_full_min 0.826
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# 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_s4497ma
_database_code_depnum_ccdc_archive 'CCDC 2009903'
loop_
_audit_author_name
_audit_author_address
'Sarah Wright'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------# 

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-aminobenzoic acid acetone solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 N2 O5'
_chemical_formula_weight         332.35

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0395(2)
_cell_length_b                   8.2374(3)
_cell_length_c                   20.4205(7)
_cell_angle_alpha                88.805(2)
_cell_angle_beta                 83.313(2)
_cell_angle_gamma                84.487(2)
_cell_volume                     838.00(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4642
_cell_measurement_theta_min      6.55
_cell_measurement_theta_max      72.23

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.813
_shelx_estimated_absorpt_T_min   0.810
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.858713
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8371
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         5.841
_diffrn_reflns_theta_max         72.313
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             3161
_reflns_number_gt                2878
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+0.2650P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3161
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.2859(2) 0.11918(14) 0.45805(6) 0.0210(3) Uani 1 1 d . . . . .
C2 C 0.4901(2) 0.21770(14) 0.42475(6) 0.0210(3) Uani 1 1 d . . . . .
C3 C 0.6257(3) 0.32183(15) 0.45941(6) 0.0239(3) Uani 1 1 d . . . . .
H3 H 0.5914 0.3265 0.5061 0.029 Uiso 1 1 calc R U . . .
C4 C 0.8091(3) 0.41809(15) 0.42649(7) 0.0253(3) Uani 1 1 d . . . . .
H4 H 0.9005 0.4877 0.4508 0.030 Uiso 1 1 calc R U . . .
C5 C 0.8614(2) 0.41402(14) 0.35787(7) 0.0225(3) Uani 1 1 d . . . . .
C6 C 0.7292(3) 0.30660(16) 0.32324(7) 0.0259(3) Uani 1 1 d . . . . .
H6 H 0.7662 0.2999 0.2766 0.031 Uiso 1 1 calc R U . . .
C7 C 0.5469(3) 0.21118(15) 0.35631(7) 0.0247(3) Uani 1 1 d . . . . .
H7 H 0.4583 0.1397 0.3322 0.030 Uiso 1 1 calc R U . . .
C8 C 0.1234(3) 0.93542(16) 0.08330(7) 0.0306(3) Uani 1 1 d . . . . .
C9 C 0.2147(3) 0.88898(15) 0.14727(7) 0.0264(3) Uani 1 1 d . . . . .
C10 C 0.0754(3) 0.95755(16) 0.20476(7) 0.0273(3) Uani 1 1 d . . . . .
H10 H -0.0795 1.0316 0.2019 0.033 Uiso 1 1 calc R U . . .
C11 C 0.1594(3) 0.91950(15) 0.26549(7) 0.0251(3) Uani 1 1 d . . . . .
H11 H 0.0618 0.9669 0.3041 0.030 Uiso 1 1 calc R U . . .
C12 C 0.3892(3) 0.81067(14) 0.27049(7) 0.0230(3) Uani 1 1 d . . . . .
C13 C 0.5274(3) 0.74090(16) 0.21295(7) 0.0277(3) Uani 1 1 d . . . . .
H13 H 0.6816 0.6661 0.2156 0.033 Uiso 1 1 calc R U . . .
C14 C 0.4418(3) 0.77970(16) 0.15235(7) 0.0282(3) Uani 1 1 d . . . . .
H14 H 0.5380 0.7317 0.1137 0.034 Uiso 1 1 calc R U . . .
C15 C 0.4540(4) 0.2923(3) 0.15725(14) 0.0640(6) Uani 1 1 d . . . . .
H15A H 0.6076 0.3578 0.1519 0.096 Uiso 1 1 calc R U . . .
H15B H 0.4941 0.1952 0.1296 0.096 Uiso 1 1 calc R U . . .
H15C H 0.4186 0.2589 0.2035 0.096 Uiso 1 1 calc R U . . .
C16 C 0.2141(3) 0.39075(17) 0.13710(7) 0.0302(3) Uani 1 1 d . . . . .
C17 C 0.1974(6) 0.4215(3) 0.06574(10) 0.0759(8) Uani 1 1 d . . . . .
H17A H 0.1520 0.3226 0.0454 0.114 Uiso 1 1 calc R U . . .
H17B H 0.3708 0.4514 0.0445 0.114 Uiso 1 1 calc R U . . .
H17C H 0.0584 0.5108 0.0602 0.114 Uiso 1 1 calc R U . . .
N1 N 1.0254(2) 0.51900(14) 0.32401(6) 0.0283(3) Uani 1 1 d . . . . .
N2 N 0.4698(2) 0.76870(14) 0.33136(6) 0.0278(3) Uani 1 1 d . . . . .
O1 O 0.17672(18) 0.01895(11) 0.42896(4) 0.0246(2) Uani 1 1 d . . . . .
O2 O 0.22537(18) 0.14634(11) 0.52184(4) 0.0256(2) Uani 1 1 d . . . . .
H2 H 0.1019 0.0896 0.5369 0.038 Uiso 1 1 calc R U . . .
O3 O -0.0630(3) 1.04246(15) 0.07814(5) 0.0458(3) Uani 1 1 d . . . . .
O4 O 0.2511(3) 0.85734(14) 0.03204(5) 0.0445(3) Uani 1 1 d . . . . .
H4A H 0.1899 0.8943 -0.0024 0.067 Uiso 1 1 calc R U . . .
O5 O 0.0387(2) 0.44446(15) 0.17778(6) 0.0434(3) Uani 1 1 d . . . . .
H2A H 0.640(4) 0.721(2) 0.3302(9) 0.038(5) Uiso 1 1 d . . . . .
H2B H 0.412(4) 0.837(2) 0.3633(9) 0.038(5) Uiso 1 1 d . . . . .
H1A H 1.141(4) 0.563(2) 0.3460(9) 0.040(5) Uiso 1 1 d . . . . .
H1B H 1.070(4) 0.498(2) 0.2806(10) 0.040(5) Uiso 1 1 d . . . . .


_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
C1 O1 1.2333(15) . ?
C1 O2 1.3216(15) . ?
C1 C2 1.4679(17) . ?
C2 C7 1.3946(18) . ?
C2 C3 1.3979(18) . ?
C3 C4 1.3816(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3958(19) . ?
C4 H4 0.9500 . ?
C5 N1 1.3742(17) . ?
C5 C6 1.4057(18) . ?
C6 C7 1.3748(19) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 O3 1.2372(18) . ?
C8 O4 1.3098(18) . ?
C8 C9 1.4662(19) . ?
C9 C10 1.396(2) . ?
C9 C14 1.3991(19) . ?
C10 C11 1.3767(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.4069(18) . ?
C11 H11 0.9500 . ?
C12 N2 1.3793(17) . ?
C12 C13 1.3989(19) . ?
C13 C14 1.379(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.484(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O5 1.1985(18) . ?
C16 C17 1.485(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N1 H1A 0.88(2) . ?
N1 H1B 0.91(2) . ?
N2 H2A 0.904(19) . ?
N2 H2B 0.88(2) . ?
O2 H2 0.8400 . ?
O4 H4A 0.8400 . ?

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
O1 C1 O2 122.08(11) . . ?
O1 C1 C2 122.88(11) . . ?
O2 C1 C2 115.03(11) . . ?
C7 C2 C3 118.59(11) . . ?
C7 C2 C1 119.41(11) . . ?
C3 C2 C1 121.97(11) . . ?
C4 C3 C2 120.72(12) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.60(12) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N1 C5 C4 121.28(12) . . ?
N1 C5 C6 120.03(12) . . ?
C4 C5 C6 118.57(12) . . ?
C7 C6 C5 120.49(12) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C2 120.99(12) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
O3 C8 O4 122.06(13) . . ?
O3 C8 C9 121.84(13) . . ?
O4 C8 C9 116.10(12) . . ?
C10 C9 C14 118.77(12) . . ?
C10 C9 C8 119.49(12) . . ?
C14 C9 C8 121.73(13) . . ?
C11 C10 C9 120.99(12) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.20(12) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
N2 C12 C13 120.72(12) . . ?
N2 C12 C11 120.42(12) . . ?
C13 C12 C11 118.82(12) . . ?
C14 C13 C12 120.57(12) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C9 120.65(13) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O5 C16 C15 120.44(17) . . ?
O5 C16 C17 121.00(18) . . ?
C15 C16 C17 118.56(19) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 N1 H1A 117.5(12) . . ?
C5 N1 H1B 115.5(12) . . ?
H1A N1 H1B 119.2(17) . . ?
C12 N2 H2A 114.8(12) . . ?
C12 N2 H2B 116.0(12) . . ?
H2A N2 H2B 117.6(17) . . ?
C1 O2 H2 109.5 . . ?
C8 O4 H4A 109.5 . . ?

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
O1 C1 C2 C7 6.51(18) . . . . ?
O2 C1 C2 C7 -173.07(11) . . . . ?
O1 C1 C2 C3 -175.18(11) . . . . ?
O2 C1 C2 C3 5.24(16) . . . . ?
C7 C2 C3 C4 0.96(18) . . . . ?
C1 C2 C3 C4 -177.35(11) . . . . ?
C2 C3 C4 C5 0.42(19) . . . . ?
C3 C4 C5 N1 174.30(12) . . . . ?
C3 C4 C5 C6 -1.79(19) . . . . ?
N1 C5 C6 C7 -174.34(12) . . . . ?
C4 C5 C6 C7 1.80(19) . . . . ?
C5 C6 C7 C2 -0.4(2) . . . . ?
C3 C2 C7 C6 -0.95(19) . . . . ?
C1 C2 C7 C6 177.41(11) . . . . ?
O3 C8 C9 C10 5.1(2) . . . . ?
O4 C8 C9 C10 -175.08(13) . . . . ?
O3 C8 C9 C14 -173.60(14) . . . . ?
O4 C8 C9 C14 6.2(2) . . . . ?
C14 C9 C10 C11 0.2(2) . . . . ?
C8 C9 C10 C11 -178.49(12) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 N2 -178.21(12) . . . . ?
C10 C11 C12 C13 -0.82(19) . . . . ?
N2 C12 C13 C14 178.19(12) . . . . ?
C11 C12 C13 C14 0.80(19) . . . . ?
C12 C13 C14 C9 -0.3(2) . . . . ?
C10 C9 C14 C13 -0.3(2) . . . . ?
C8 C9 C14 C13 178.44(12) . . . . ?

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
C6 H6 O5 0.95 2.64 3.4153(18) 139.6 1_655
C13 H13 O5 0.95 2.50 3.3987(17) 156.8 1_655
C15 H15A O5 0.98 2.47 3.383(2) 155.5 1_655
C15 H15B O3 0.98 2.58 3.321(2) 132.8 1_645
O2 H2 O1 0.84 1.80 2.6397(12) 176.0 2_556
O4 H4A O3 0.84 1.79 2.6290(15) 175.6 2_575
N2 H2A N1 0.904(19) 2.43(2) 3.3018(17) 162.4(16) .
N2 H2B O1 0.88(2) 2.20(2) 3.0502(16) 165.0(16) 1_565
N1 H1A N2 0.88(2) 2.47(2) 3.2007(17) 140.3(15) 1_655
N1 H1B O5 0.91(2) 2.18(2) 3.0528(18) 161.7(17) 1_655

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone/Water'
