# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_oacc123
_database_code_depnum_ccdc_archive 'CCDC 2069403'
loop_
_audit_author_name
_audit_author_address
'Pietro Sacchi'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-04-20 downloaded from the CCDC.
;
_audit_creation_date             2021-02-09
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
'Clotam, Tolfedine,2-[(3-Chloro-2-methylphenyl)amino]benzoic Acid'
_chemical_name_systematic        'tolfenamic acid'
_chemical_formula_moiety         'C14 H12 Cl N O2'
_chemical_formula_sum            'C14 H12 Cl N O2'
_chemical_formula_weight         261.70
_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'
Cl Cl 0.1484 0.1585 '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                   10.5841(11)
_cell_length_b                   7.8503(6)
_cell_length_c                   14.9718(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.399(9)
_cell_angle_gamma                90
_cell_volume                     1219.44(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3219
_cell_measurement_temperature    293.3(7)
_cell_measurement_theta_max      23.2580
_cell_measurement_theta_min      3.4060
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
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_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16842
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.577
_diffrn_reflns_theta_min         2.776
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.3(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1636
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  39.00   1.00   50.00    --  -10.25  77.00  30.00   81
  2  ω    -39.00  21.00   1.00   50.00    --  -10.25 -77.00 -90.00   60
  3  ω    -42.00  39.00   1.00   50.00    --  -10.25  77.00 -90.00   81
  4  ω    -39.00  41.00   1.00   50.00    --    9.93 -77.00-180.00   80
  5  ω    -80.00  16.00   1.00   50.00    --  -10.25 -57.00-150.00   96
  6  ω    -80.00 -55.00   1.00   50.00    --  -10.25 -57.00  30.00   25
  7  ω    -39.00  11.00   1.00   50.00    --  -10.25 -77.00  90.00   50
;
_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      -0.0162852000
_diffrn_orient_matrix_UB_12      0.0139249000
_diffrn_orient_matrix_UB_13      -0.0477113000
_diffrn_orient_matrix_UB_21      0.0615698000
_diffrn_orient_matrix_UB_22      -0.0301891000
_diffrn_orient_matrix_UB_23      -0.0045134000
_diffrn_orient_matrix_UB_31      -0.0248245000
_diffrn_orient_matrix_UB_32      -0.0840310000
_diffrn_orient_matrix_UB_33      -0.0062794000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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                1692
_reflns_number_total             3119
_reflns_odcompleteness_completeness 99.81
_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 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3119
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.039
_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)+(0.0379P)²+0.1049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1247
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
3.a Aromatic/amide H refined with riding coordinates:
 C3(H2), C4(H3), C5(H4), C6(H5), C9(H7), C10(H8), C11(H9)
3.b Idealised Me refined as rotating group:
 C14(H10,H11,H12)
;
_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 -0.09267(7) -0.35352(8) 0.07016(4) 0.0554(2) Uani 1 1 d . . . . .
O1 O 0.49299(19) 0.2265(2) 0.47456(13) 0.0650(6) Uani 1 1 d D . . . .
N1 N 0.2673(2) 0.0441(3) 0.23009(14) 0.0522(6) Uani 1 1 d D . . . .
H6 H 0.287(2) -0.015(3) 0.2778(13) 0.054(8) Uiso 1 1 d D . . . .
C1 C 0.4222(2) 0.1546(3) 0.40246(16) 0.0446(6) Uani 1 1 d . . . . .
O2 O 0.39827(17) 0.0004(2) 0.40131(11) 0.0550(5) Uani 1 1 d . . . . .
C2 C 0.3770(2) 0.2699(3) 0.32654(15) 0.0401(6) Uani 1 1 d . . . . .
C3 C 0.4081(2) 0.4438(3) 0.33651(18) 0.0478(6) Uani 1 1 d . . . . .
H2 H 0.454040 0.482674 0.392213 0.057 Uiso 1 1 calc R U . . .
C4 C 0.3728(3) 0.5580(3) 0.26676(19) 0.0562(7) Uani 1 1 d . . . . .
H3 H 0.395759 0.672145 0.274585 0.067 Uiso 1 1 calc R U . . .
C5 C 0.3026(3) 0.5002(3) 0.18458(19) 0.0546(7) Uani 1 1 d . . . . .
H4 H 0.278401 0.576625 0.136818 0.066 Uiso 1 1 calc R U . . .
C6 C 0.2680(2) 0.3323(3) 0.17217(17) 0.0492(6) Uani 1 1 d . . . . .
H5 H 0.219748 0.297534 0.116344 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3036(2) 0.2119(3) 0.24177(15) 0.0403(6) Uani 1 1 d . . . . .
C8 C 0.2029(2) -0.0348(3) 0.14839(15) 0.0418(6) Uani 1 1 d . . . . .
C9 C 0.2464(2) -0.0145(3) 0.06774(17) 0.0488(6) Uani 1 1 d . . . . .
H7 H 0.317501 0.054460 0.066420 0.059 Uiso 1 1 calc R U . . .
C10 C 0.1852(3) -0.0956(3) -0.01073(17) 0.0504(7) Uani 1 1 d . . . . .
H8 H 0.214454 -0.079794 -0.064782 0.061 Uiso 1 1 calc R U . . .
C11 C 0.0816(2) -0.1993(3) -0.00923(15) 0.0446(6) Uani 1 1 d . . . . .
H9 H 0.039964 -0.253968 -0.062002 0.053 Uiso 1 1 calc R U . . .
C12 C 0.0400(2) -0.2215(3) 0.07133(15) 0.0385(6) Uani 1 1 d . . . . .
C13 C 0.0979(2) -0.1411(3) 0.15233(15) 0.0380(6) Uani 1 1 d . . . . .
C14 C 0.0505(3) -0.1689(3) 0.23941(16) 0.0586(7) Uani 1 1 d . . . . .
H10 H 0.081533 -0.276433 0.265397 0.088 Uiso 1 1 calc R U . . .
H11 H -0.041975 -0.168760 0.226910 0.088 Uiso 1 1 calc R U . . .
H12 H 0.081811 -0.079122 0.281570 0.088 Uiso 1 1 calc R U . . .
H1 H 0.526(3) 0.151(3) 0.5119(18) 0.091(12) Uiso 1 1 d 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 C12 1.743(2) . ?
O1 C1 1.314(3) . ?
O1 H1 0.842(17) . ?
N1 H6 0.842(16) . ?
N1 C7 1.373(3) . ?
N1 C8 1.420(3) . ?
C1 O2 1.236(3) . ?
C1 C2 1.458(3) . ?
C2 C3 1.405(3) . ?
C2 C7 1.426(3) . ?
C3 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C4 H3 0.9300 . ?
C4 C5 1.382(4) . ?
C5 H4 0.9300 . ?
C5 C6 1.370(3) . ?
C6 H5 0.9300 . ?
C6 C7 1.402(3) . ?
C8 C9 1.384(3) . ?
C8 C13 1.400(3) . ?
C9 H7 0.9300 . ?
C9 C10 1.380(3) . ?
C10 H8 0.9300 . ?
C10 C11 1.370(3) . ?
C11 H9 0.9300 . ?
C11 C12 1.374(3) . ?
C12 C13 1.397(3) . ?
C13 C14 1.502(3) . ?
C14 H10 0.9600 . ?
C14 H11 0.9600 . ?
C14 H12 0.9600 . ?

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 O1 H1 109(2) . . ?
C7 N1 H6 113.9(17) . . ?
C7 N1 C8 127.1(2) . . ?
C8 N1 H6 119.0(17) . . ?
O1 C1 C2 114.8(2) . . ?
O2 C1 O1 120.9(2) . . ?
O2 C1 C2 124.2(2) . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 C7 118.7(2) . . ?
C7 C2 C1 122.2(2) . . ?
C2 C3 H2 118.9 . . ?
C4 C3 C2 122.1(2) . . ?
C4 C3 H2 118.9 . . ?
C3 C4 H3 120.6 . . ?
C3 C4 C5 118.8(2) . . ?
C5 C4 H3 120.6 . . ?
C4 C5 H4 119.4 . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H4 119.4 . . ?
C5 C6 H5 119.3 . . ?
C5 C6 C7 121.5(2) . . ?
C7 C6 H5 119.3 . . ?
N1 C7 C2 120.6(2) . . ?
N1 C7 C6 121.7(2) . . ?
C6 C7 C2 117.7(2) . . ?
C9 C8 N1 121.0(2) . . ?
C9 C8 C13 120.6(2) . . ?
C13 C8 N1 118.3(2) . . ?
C8 C9 H7 119.7 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H7 119.7 . . ?
C9 C10 H8 119.9 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H8 119.9 . . ?
C10 C11 H9 120.5 . . ?
C10 C11 C12 119.1(2) . . ?
C12 C11 H9 120.5 . . ?
C11 C12 Cl1 117.62(18) . . ?
C11 C12 C13 122.9(2) . . ?
C13 C12 Cl1 119.46(18) . . ?
C8 C13 C14 121.8(2) . . ?
C12 C13 C8 116.6(2) . . ?
C12 C13 C14 121.6(2) . . ?
C13 C14 H10 109.5 . . ?
C13 C14 H11 109.5 . . ?
C13 C14 H12 109.5 . . ?
H10 C14 H11 109.5 . . ?
H10 C14 H12 109.5 . . ?
H11 C14 H12 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
Cl1 C12 C13 C8 -179.09(16) . . . . ?
Cl1 C12 C13 C14 1.5(3) . . . . ?
O1 C1 C2 C3 -1.8(3) . . . . ?
O1 C1 C2 C7 177.4(2) . . . . ?
N1 C8 C9 C10 178.2(2) . . . . ?
N1 C8 C13 C12 -177.68(19) . . . . ?
N1 C8 C13 C14 1.8(3) . . . . ?
C1 C2 C3 C4 177.5(2) . . . . ?
C1 C2 C7 N1 3.1(4) . . . . ?
C1 C2 C7 C6 -178.2(2) . . . . ?
O2 C1 C2 C3 178.6(2) . . . . ?
O2 C1 C2 C7 -2.2(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C2 C7 N1 -177.8(2) . . . . ?
C3 C2 C7 C6 1.0(3) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C7 -0.8(4) . . . . ?
C5 C6 C7 N1 179.0(2) . . . . ?
C5 C6 C7 C2 0.2(4) . . . . ?
C7 N1 C8 C9 49.6(4) . . . . ?
C7 N1 C8 C13 -133.6(2) . . . . ?
C7 C2 C3 C4 -1.7(4) . . . . ?
C8 N1 C7 C2 -175.0(2) . . . . ?
C8 N1 C7 C6 6.3(4) . . . . ?
C8 C9 C10 C11 -0.9(4) . . . . ?
C9 C8 C13 C12 -0.9(3) . . . . ?
C9 C8 C13 C14 178.5(2) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 Cl1 179.65(18) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C12 C13 C8 -0.2(3) . . . . ?
C11 C12 C13 C14 -179.7(2) . . . . ?
C13 C8 C9 C10 1.5(4) . . . . ?

_olex2_date_sample_data_collection 2020-03-16
_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 1.028
_oxdiff_exptl_absorpt_empirical_full_min 0.964
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 2-propanol'
