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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1861886'
loop_
_audit_author_name
_audit_author_address
'Tain?ra Orlando'
;UFSM
Brazil
;
_audit_update_record             
;
2018-08-13 deposited with the CCDC.	2019-08-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT183_shelx               
;
PROBLEM: Missing _cell_measurement_reflns_used Value ....     Please Do !
RESPONSE: We do not have access to this data since we used data from the literature for the refinement.
;
_vrf_PLAT184_shelx               
;
PROBLEM: Missing _cell_measurement_theta_min Value ......     Please Do !
RESPONSE: We do not have access to this data since we used data from the literature for the refinement.
;
_vrf_PLAT185_shelx               
;
PROBLEM: Missing _cell_measurement_theta_max Value ......     Please Do !
RESPONSE: We do not have access to this data since we used data from the literature for the refinement.
;
_vrf_PLAT881_shelx               
;
PROBLEM: No Datum for _diffrn_reflns_av_R_equivalents ...     Please Do !
RESPONSE: We do not have access to this data since we used data from the literature for the refinement.
;
# Added during the CSD deposition process: Monday 13 August 2018 07:35 PM
# end Validation Reply Form


_audit_creation_date             2018-08-13T15:32:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        '2-[(2,6-dimethylphenyl)amino]benzoic acid'
_chemical_name_common            '2-[(2,6-dimethylphenyl)amino]benzoic acid'
_chemical_formula_moiety         'C7.50 H7.50 N0.50 O'
_chemical_formula_sum            'C7.50 H7.50 N0.50 O'
_chemical_formula_weight         120.64
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5311(7)
_cell_length_b                   8.0960(9)
_cell_length_c                   11.1845(12)
_cell_angle_alpha                72.496(10)
_cell_angle_beta                 83.728(9)
_cell_angle_gamma                73.792(17)
_cell_volume                     624.28(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71069

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   graphite-monochromated
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'Rigaku AFC6S'
_diffrn_measurement_method       omega-2theta
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_unetI/netI     0.0038
_diffrn_reflns_number            2863
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         27.447
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             2863
_reflns_number_gt                2809
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+0.1123P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2863
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.037
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.12
_refine_ls_restrained_S_all      1.12
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.2
_refine_diff_density_rms         0.029

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.06867(11) 0.80093(11) 0.10275(8) 0.0531(2) Uani 1 1 d . . . . .
O1 O 0.24751(12) 0.95143(11) -0.03085(9) 0.0575(3) Uani 1 1 d . . . . .
H1 H 0.146818 1.023171 -0.049734 0.086 Uiso 1 1 calc R U . . .
N1 N 0.23214(12) 0.47569(11) 0.25716(8) 0.0410(2) Uani 1 1 d . . . . .
C1 C 0.39373(13) 0.67295(12) 0.10285(9) 0.0336(2) Uani 1 1 d . . . . .
C2 C 0.39269(13) 0.51222(12) 0.19889(8) 0.0315(2) Uani 1 1 d . . . . .
C8 C 0.23400(13) 0.35059(12) 0.38026(9) 0.0361(2) Uani 1 1 d . . . . .
C13 C 0.24314(14) 0.40745(13) 0.48472(10) 0.0390(2) Uani 1 1 d . . . . .
C6 C 0.56277(15) 0.70081(15) 0.04816(10) 0.0427(2) Uani 1 1 d . . . . .
H6 H 0.563576 0.806483 -0.014552 0.051 Uiso 1 1 calc R U . . .
C12 C 0.24498(17) 0.28654(15) 0.60276(11) 0.0457(3) Uani 1 1 d . . . . .
H12 H 0.249071 0.323585 0.673229 0.055 Uiso 1 1 calc R U . . .
C7 C 0.22422(15) 0.81129(13) 0.05998(9) 0.0389(2) Uani 1 1 d . . . . .
C9 C 0.23172(14) 0.17354(13) 0.39175(10) 0.0400(2) Uani 1 1 d . . . . .
C15 C 0.24854(18) 0.59633(16) 0.47052(14) 0.0540(3) Uani 1 1 d . . . . .
H15A H 0.24639 0.66138 0.383152 0.081 Uiso 1 1 calc R U . . .
H15B H 0.142977 0.653548 0.513426 0.081 Uiso 1 1 calc R U . . .
H15C H 0.359687 0.594892 0.505901 0.081 Uiso 1 1 calc R U . . .
C11 C 0.24084(18) 0.11234(15) 0.61759(11) 0.0490(3) Uani 1 1 d . . . . .
H11 H 0.242479 0.032352 0.697296 0.059 Uiso 1 1 calc R U . . .
C10 C 0.23422(17) 0.05782(14) 0.51244(11) 0.0487(3) Uani 1 1 d . . . . .
H10 H 0.231354 -0.059782 0.522826 0.058 Uiso 1 1 calc R U . . .
C5 C 0.72834(16) 0.57615(18) 0.08451(12) 0.0514(3) Uani 1 1 d . . . . .
H5 H 0.839669 0.597449 0.047678 0.062 Uiso 1 1 calc R U . . .
C3 C 0.56302(15) 0.38785(14) 0.23354(11) 0.0431(2) Uani 1 1 d . . . . .
H3 H 0.565648 0.281726 0.29659 0.052 Uiso 1 1 calc R U . . .
C4 C 0.72530(16) 0.41887(17) 0.17686(12) 0.0494(3) Uani 1 1 d . . . . .
H4 H 0.835828 0.332502 0.200866 0.059 Uiso 1 1 calc R U . . .
C14 C 0.2308(2) 0.10740(17) 0.28044(12) 0.0548(3) Uani 1 1 d . . . . .
H14A H 0.229052 0.203793 0.205012 0.082 Uiso 1 1 calc R U . . .
H14B H 0.33982 0.01173 0.279628 0.082 Uiso 1 1 calc R U . . .
H14C H 0.12298 0.064263 0.285317 0.082 Uiso 1 1 calc R U . . .
H1B H 0.1191(19) 0.5332(18) 0.2161(12) 0.046(3) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C7 1.2314(13) . ?
O1 C7 1.3149(11) . ?
O1 H1 0.82 . ?
N1 C2 1.3732(13) . ?
N1 C8 1.4419(12) . ?
N1 H1B 0.942(14) . ?
C1 C6 1.3974(14) . ?
C1 C2 1.4178(13) . ?
C1 C7 1.4582(14) . ?
C2 C3 1.4009(14) . ?
C8 C13 1.3931(15) . ?
C8 C9 1.4049(13) . ?
C13 C12 1.3858(15) . ?
C13 C15 1.5008(15) . ?
C6 C5 1.3785(17) . ?
C6 H6 0.93 . ?
C12 C11 1.3784(16) . ?
C12 H12 0.93 . ?
C9 C10 1.3910(15) . ?
C9 C14 1.4972(16) . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
C11 C10 1.3849(18) . ?
C11 H11 0.93 . ?
C10 H10 0.93 . ?
C5 C4 1.3815(18) . ?
C5 H5 0.93 . ?
C3 C4 1.3656(16) . ?
C3 H3 0.93 . ?
C4 H4 0.93 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 109.5 . . ?
C2 N1 C8 120.96(8) . . ?
C2 N1 H1B 119.5(8) . . ?
C8 N1 H1B 119.5(8) . . ?
C6 C1 C2 119.02(9) . . ?
C6 C1 C7 118.79(9) . . ?
C2 C1 C7 122.18(9) . . ?
N1 C2 C3 119.88(9) . . ?
N1 C2 C1 122.33(8) . . ?
C3 C2 C1 117.79(9) . . ?
C13 C8 C9 121.68(9) . . ?
C13 C8 N1 118.96(9) . . ?
C9 C8 N1 119.34(10) . . ?
C12 C13 C8 118.67(9) . . ?
C12 C13 C15 120.38(11) . . ?
C8 C13 C15 120.95(10) . . ?
C5 C6 C1 121.88(10) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
C11 C12 C13 121.19(11) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
O2 C7 O1 120.99(9) . . ?
O2 C7 C1 123.98(9) . . ?
O1 C7 C1 115.02(9) . . ?
C10 C9 C8 117.18(10) . . ?
C10 C9 C14 120.28(10) . . ?
C8 C9 C14 122.53(10) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C11 C10 119.23(10) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C10 C9 122.03(10) . . ?
C11 C10 H10 119 . . ?
C9 C10 H10 119 . . ?
C6 C5 C4 118.55(10) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C4 C3 C2 121.51(10) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 121.23(10) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C8 N1 C2 C3 23.13(15) . . . . ?
C8 N1 C2 C1 -157.22(9) . . . . ?
C6 C1 C2 N1 179.85(9) . . . . ?
C7 C1 C2 N1 0.48(15) . . . . ?
C6 C1 C2 C3 -0.50(15) . . . . ?
C7 C1 C2 C3 -179.87(9) . . . . ?
C2 N1 C8 C13 79.61(13) . . . . ?
C2 N1 C8 C9 -98.65(12) . . . . ?
C9 C8 C13 C12 -1.75(16) . . . . ?
N1 C8 C13 C12 -179.97(9) . . . . ?
C9 C8 C13 C15 179.01(10) . . . . ?
N1 C8 C13 C15 0.79(15) . . . . ?
C2 C1 C6 C5 0.31(16) . . . . ?
C7 C1 C6 C5 179.70(10) . . . . ?
C8 C13 C12 C11 1.01(17) . . . . ?
C15 C13 C12 C11 -179.74(11) . . . . ?
C6 C1 C7 O2 -179.22(10) . . . . ?
C2 C1 C7 O2 0.15(17) . . . . ?
C6 C1 C7 O1 1.51(15) . . . . ?
C2 C1 C7 O1 -179.12(9) . . . . ?
C13 C8 C9 C10 1.60(16) . . . . ?
N1 C8 C9 C10 179.81(9) . . . . ?
C13 C8 C9 C14 -177.09(10) . . . . ?
N1 C8 C9 C14 1.12(16) . . . . ?
C13 C12 C11 C10 -0.18(19) . . . . ?
C12 C11 C10 C9 0.05(19) . . . . ?
C8 C9 C10 C11 -0.73(17) . . . . ?
C14 C9 C10 C11 177.98(11) . . . . ?
C1 C6 C5 C4 0.65(18) . . . . ?
N1 C2 C3 C4 179.38(10) . . . . ?
C1 C2 C3 C4 -0.28(16) . . . . ?
C2 C3 C4 C5 1.29(19) . . . . ?
C6 C5 C4 C3 -1.46(19) . . . . ?


# END of CIF
