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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_insa_ambient
_database_code_depnum_ccdc_archive 'CCDC 1902709'
loop_
_audit_author_name
_audit_author_address
'Iain Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-06-11 downloaded from the CCDC.
;
_audit_creation_date             2019-02-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid 1,2-benzisothiazol-3(2H)-one 1,1-dioxide'
_chemical_formula_moiety         'C19 H16 Cl N O4, C7 H5 N O3 S'
_chemical_formula_sum            'C26 H21 Cl N2 O7 S'
_chemical_formula_weight         540.96
_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'
S S 0.1246 0.1234 '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                   7.1314(2)
_cell_length_b                   10.4809(2)
_cell_length_c                   16.7109(4)
_cell_angle_alpha                80.5779(12)
_cell_angle_beta                 86.4941(12)
_cell_angle_gamma                79.2821(12)
_cell_volume                     1210.08(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6585
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.338
_cell_measurement_theta_min      2.472
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0807 before and 0.0443 after correction. The Ratio of minimum to maximum transmission is 0.9327. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_recrystallization_method 
'Recrystallisation of indomethacin and saccharin in a 1:1 molar ratio'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26677
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.509
_diffrn_reflns_theta_min         2.002
_diffrn_ambient_temperature      123.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          
'Data were collected on a crystal at ambient pressure'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4504
_reflns_number_total             7292
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         7292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.057
_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)+(0.0500P)²+0.2309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1246
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C19(H19), C23(H23), C24(H24), N26(H26),
 C30(H30), C31(H31), C32(H32), C33(H33)
2.c Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C22(H22a,H22b,H22c)
2.d Idealised tetrahedral OH refined as rotating group:
 O16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.27310(11) 0.60235(8) 0.37380(4) 0.0841(3) Uani 1 1 d . . . . .
C2 C 0.2444(3) 0.6457(2) 0.47080(13) 0.0485(5) Uani 1 1 d . . . . .
C3 C 0.2137(3) 0.7772(2) 0.47769(12) 0.0414(5) Uani 1 1 d . . . . .
H3 H 0.2080 0.8427 0.4309 0.050 Uiso 1 1 calc R . . . .
C4 C 0.1914(2) 0.8110(2) 0.55467(11) 0.0360(4) Uani 1 1 d . . . . .
H4 H 0.1678 0.9012 0.5609 0.043 Uiso 1 1 calc R . . . .
C5 C 0.2032(2) 0.71506(18) 0.62299(11) 0.0335(4) Uani 1 1 d . . . . .
C6 C 0.2387(3) 0.5840(2) 0.61363(13) 0.0501(5) Uani 1 1 d . . . . .
H6 H 0.2505 0.5176 0.6601 0.060 Uiso 1 1 calc R . . . .
C7 C 0.2570(4) 0.5494(2) 0.53679(14) 0.0594(6) Uani 1 1 d . . . . .
H7 H 0.2781 0.4595 0.5301 0.071 Uiso 1 1 calc R . . . .
C8 C 0.1918(2) 0.74777(18) 0.70674(11) 0.0324(4) Uani 1 1 d . . . . .
O9 O 0.3048(2) 0.68861(14) 0.75698(8) 0.0484(4) Uani 1 1 d . . . . .
N10 N 0.04810(19) 0.85028(14) 0.72471(8) 0.0293(3) Uani 1 1 d . . . . .
C11 C 0.0522(2) 0.92149(17) 0.78971(10) 0.0296(4) Uani 1 1 d . . . . .
C12 C 0.2232(3) 0.90648(19) 0.83992(12) 0.0384(4) Uani 1 1 d . . . . .
H12A H 0.2333 0.8247 0.8787 0.058 Uiso 1 1 calc GR . . . .
H12B H 0.2103 0.9812 0.8695 0.058 Uiso 1 1 calc GR . . . .
H12C H 0.3382 0.9037 0.8045 0.058 Uiso 1 1 calc GR . . . .
C13 C -0.1155(2) 1.00663(17) 0.79307(10) 0.0282(4) Uani 1 1 d . . . . .
C14 C -0.1773(3) 1.09904(18) 0.85281(11) 0.0324(4) Uani 1 1 d . . . . .
H14A H -0.2362 1.1856 0.8232 0.039 Uiso 1 1 calc R . . . .
H14B H -0.0632 1.1114 0.8795 0.039 Uiso 1 1 calc R . . . .
C15 C -0.3172(2) 1.05278(17) 0.91702(10) 0.0290(4) Uani 1 1 d . . . . .
O16 O -0.3737(2) 1.13616(13) 0.96727(8) 0.0440(3) Uani 1 1 d . . . . .
H16 H -0.4545 1.1076 1.0008 0.066 Uiso 1 1 calc GR . . . .
O17 O -0.3739(2) 0.94947(13) 0.92080(8) 0.0424(3) Uani 1 1 d . . . . .
C18 C -0.2334(2) 0.99148(16) 0.72972(10) 0.0267(3) Uani 1 1 d . . . . .
C19 C -0.4169(2) 1.05452(18) 0.70774(11) 0.0315(4) Uani 1 1 d . . . . .
H19 H -0.4852 1.1217 0.7356 0.038 Uiso 1 1 calc R . . . .
C20 C -0.4963(2) 1.01644(19) 0.64427(11) 0.0359(4) Uani 1 1 d . . . . .
O21 O -0.67292(19) 1.07296(15) 0.61436(9) 0.0543(4) Uani 1 1 d . . . . .
C22 C -0.7715(3) 1.1844(2) 0.64675(17) 0.0626(7) Uani 1 1 d . . . . .
H22A H -0.8904 1.2191 0.6180 0.094 Uiso 1 1 calc GR . . . .
H22B H -0.6913 1.2521 0.6401 0.094 Uiso 1 1 calc GR . . . .
H22C H -0.8010 1.1591 0.7046 0.094 Uiso 1 1 calc GR . . . .
C23 C -0.3982(3) 0.9146(2) 0.60544(12) 0.0403(5) Uani 1 1 d . . . . .
H23 H -0.4572 0.8887 0.5628 0.048 Uiso 1 1 calc R . . . .
C24 C -0.2175(3) 0.85067(19) 0.62744(11) 0.0366(4) Uani 1 1 d . . . . .
H24 H -0.1534 0.7796 0.6017 0.044 Uiso 1 1 calc R . . . .
C25 C -0.1319(2) 0.89296(17) 0.68816(10) 0.0284(4) Uani 1 1 d . . . . .
N26 N 0.6408(2) 0.57678(14) 0.07084(9) 0.0348(4) Uani 1 1 d . . . . .
H26 H 0.5291 0.6064 0.0486 0.042 Uiso 1 1 calc R . . . .
C27 C 0.7550(2) 0.46162(17) 0.05525(11) 0.0305(4) Uani 1 1 d . . . . .
O28 O 0.71330(19) 0.39087(13) 0.01127(8) 0.0424(3) Uani 1 1 d . . . . .
C29 C 0.9337(2) 0.44026(16) 0.10039(10) 0.0285(4) Uani 1 1 d . . . . .
C30 C 1.0880(3) 0.33807(17) 0.10008(11) 0.0347(4) Uani 1 1 d . . . . .
H30 H 1.0888 0.2709 0.0681 0.042 Uiso 1 1 calc R . . . .
C31 C 1.2403(3) 0.33665(19) 0.14757(12) 0.0410(5) Uani 1 1 d . . . . .
H31 H 1.3472 0.2672 0.1482 0.049 Uiso 1 1 calc R . . . .
C32 C 1.2407(3) 0.4343(2) 0.19433(13) 0.0456(5) Uani 1 1 d . . . . .
H32 H 1.3475 0.4309 0.2265 0.055 Uiso 1 1 calc R . . . .
C33 C 1.0869(3) 0.5369(2) 0.19471(12) 0.0421(5) Uani 1 1 d . . . . .
H33 H 1.0859 0.6046 0.2264 0.051 Uiso 1 1 calc R . . . .
C34 C 0.9355(2) 0.53678(17) 0.14726(11) 0.0320(4) Uani 1 1 d . . . . .
S35 S 0.72747(7) 0.65547(5) 0.13403(3) 0.03675(13) Uani 1 1 d . . . . .
O36 O 0.7711(2) 0.77723(13) 0.09366(10) 0.0551(4) Uani 1 1 d . . . . .
O37 O 0.6082(2) 0.65864(16) 0.20563(9) 0.0577(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 C2 1.744(2) . ?
C2 C3 1.378(3) . ?
C2 C7 1.363(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C5 C6 1.383(3) . ?
C5 C8 1.488(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(3) . ?
C7 H7 0.9500 . ?
C8 O9 1.211(2) . ?
C8 N10 1.398(2) . ?
N10 C11 1.420(2) . ?
N10 C25 1.419(2) . ?
C11 C12 1.492(2) . ?
C11 C13 1.357(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.494(2) . ?
C13 C18 1.437(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.504(2) . ?
C15 O16 1.3034(19) . ?
C15 O17 1.216(2) . ?
O16 H16 0.8400 . ?
C18 C19 1.393(2) . ?
C18 C25 1.403(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.379(2) . ?
C20 O21 1.374(2) . ?
C20 C23 1.394(3) . ?
O21 C22 1.417(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23 0.9500 . ?
C23 C24 1.379(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.386(2) . ?
N26 H26 0.8800 . ?
N26 C27 1.378(2) . ?
N26 S35 1.6531(15) . ?
C27 O28 1.2106(19) . ?
C27 C29 1.483(2) . ?
C29 C30 1.386(2) . ?
C29 C34 1.379(2) . ?
C30 H30 0.9500 . ?
C30 C31 1.381(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.386(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.387(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.379(3) . ?
C34 S35 1.7493(18) . ?
S35 O36 1.4215(16) . ?
S35 O37 1.4260(15) . ?

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 C2 Cl1 118.27(18) . . ?
C7 C2 Cl1 119.38(18) . . ?
C7 C2 C3 122.33(19) . . ?
C2 C3 H3 121.0 . . ?
C2 C3 C4 118.0(2) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.86(18) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C8 122.22(17) . . ?
C6 C5 C4 119.38(18) . . ?
C6 C5 C8 118.27(18) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 119.3(2) . . ?
C2 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
O9 C8 C5 121.00(16) . . ?
O9 C8 N10 121.39(16) . . ?
N10 C8 C5 117.60(15) . . ?
C8 N10 C11 124.43(14) . . ?
C8 N10 C25 127.25(14) . . ?
C25 N10 C11 108.05(13) . . ?
N10 C11 C12 123.05(15) . . ?
C13 C11 N10 108.69(14) . . ?
C13 C11 C12 128.14(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 127.67(15) . . ?
C11 C13 C18 108.49(14) . . ?
C18 C13 C14 123.81(15) . . ?
C13 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C13 C14 C15 113.68(14) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
O16 C15 C14 112.90(15) . . ?
O17 C15 C14 123.48(15) . . ?
O17 C15 O16 123.61(16) . . ?
C15 O16 H16 109.5 . . ?
C19 C18 C13 131.15(15) . . ?
C19 C18 C25 121.03(15) . . ?
C25 C18 C13 107.81(14) . . ?
C18 C19 H19 121.0 . . ?
C20 C19 C18 117.99(16) . . ?
C20 C19 H19 121.0 . . ?
C19 C20 C23 120.74(16) . . ?
O21 C20 C19 124.26(17) . . ?
O21 C20 C23 115.00(16) . . ?
C20 O21 C22 117.29(16) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23 119.2 . . ?
C24 C23 C20 121.63(17) . . ?
C24 C23 H23 119.2 . . ?
C23 C24 H24 120.9 . . ?
C23 C24 C25 118.12(16) . . ?
C25 C24 H24 120.9 . . ?
C18 C25 N10 106.94(14) . . ?
C24 C25 N10 132.62(15) . . ?
C24 C25 C18 120.31(16) . . ?
C27 N26 H26 122.2 . . ?
C27 N26 S35 115.53(12) . . ?
S35 N26 H26 122.2 . . ?
N26 C27 C29 109.12(14) . . ?
O28 C27 N26 124.46(16) . . ?
O28 C27 C29 126.42(15) . . ?
C30 C29 C27 127.69(15) . . ?
C34 C29 C27 112.33(15) . . ?
C34 C29 C30 119.98(16) . . ?
C29 C30 H30 120.9 . . ?
C31 C30 C29 118.11(17) . . ?
C31 C30 H30 120.9 . . ?
C30 C31 H31 119.3 . . ?
C30 C31 C32 121.44(17) . . ?
C32 C31 H31 119.3 . . ?
C31 C32 H32 119.7 . . ?
C31 C32 C33 120.68(17) . . ?
C33 C32 H32 119.7 . . ?
C32 C33 H33 121.4 . . ?
C34 C33 C32 117.24(18) . . ?
C34 C33 H33 121.4 . . ?
C29 C34 S35 110.44(13) . . ?
C33 C34 C29 122.55(16) . . ?
C33 C34 S35 126.98(14) . . ?
N26 S35 C34 92.54(8) . . ?
O36 S35 N26 111.24(9) . . ?
O36 S35 C34 110.44(9) . . ?
O36 S35 O37 117.15(10) . . ?
O37 S35 N26 109.73(9) . . ?
O37 S35 C34 113.07(9) . . ?

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

data_insa_4p34GPa
_database_code_depnum_ccdc_archive 'CCDC 1902714'
loop_
_audit_author_name
_audit_author_address
'Iain Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-06-11 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     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid 1,2-benzisothiazol-3(2H)-one 1,1-dioxide'
_chemical_formula_moiety         'C19 H16 Cl N O4, C7 H5 N O3 S'
_chemical_formula_sum            'C26 H21 Cl N2 O7 S'
_chemical_formula_weight         540.96
_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'
S S 0.1246 0.1234 '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                   6.7109(4)
_cell_length_b                   9.4367(12)
_cell_length_c                   16.2988(17)
_cell_angle_alpha                77.132(9)
_cell_angle_beta                 84.534(7)
_cell_angle_gamma                81.962(9)
_cell_volume                     994.17(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1347
_cell_measurement_temperature    297
_cell_measurement_theta_max      23.181
_cell_measurement_theta_min      3.251
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0702 before and 0.0505 after correction. The Ratio of minimum to maximum transmission is 0.9046. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Recrystallised from 1:1 molar ratio of indomethacin and saccharin in ethyl acetate'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.316
_diffrn_reflns_Laue_measured_fraction_max 0.316
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4363
_diffrn_reflns_point_group_measured_fraction_full 0.316
_diffrn_reflns_point_group_measured_fraction_max 0.316
_diffrn_reflns_theta_full        23.210
_diffrn_reflns_theta_max         23.210
_diffrn_reflns_theta_min         3.072
_diffrn_ambient_temperature      297.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.316
_diffrn_measured_fraction_theta_max 0.316
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          'High pressure dataset at 4.34 GPa'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                715
_reflns_number_total             898
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         898
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0651
_refine_ls_restrained_S_all      1.045
_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)+(0.0475P)²+6.5351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1526
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C2-Cl1
 0.011 with sigma of 1.742
 C5-C8
 0.011 with sigma of 1.495
 O9-C8
 0.013 with sigma of 1.217
 C8-N10
 0.021 with sigma of 1.413
 C11-N10
 0.018 with sigma of 1.398
 C25-N10
 0.015 with sigma of 1.415
 C12-C11
 0.01 with sigma of 1.491
 C11-C13
 0.007 with sigma of 1.355
 C14-C13
 0.009 with sigma of 1.502
 C18-C13
 0.015 with sigma of 1.437
 C14-C15
 0.008 with sigma of 1.506
 O16-C15
 0.023 with sigma of 1.307
 O17-C15
 0.021 with sigma of 1.213
 C19-C18
 0.012 with sigma of 1.395
 C18-C25
 0.01 with sigma of 1.406
 O21-C20
 0.011 with sigma of 1.369
 O21-C22
 0.015 with sigma of 1.425
 C27-N26
 0.013 with sigma of 1.374
 S35-N26
 0.015 with sigma of 1.654
 O28-C27
 0.011 with sigma of 1.228
 C29-C27
 0.012 with sigma of 1.483
 C34-S35
 0.008 with sigma of 1.753
 O36-S35
 0.007 with sigma of 1.431
 O37-S35
 0.007 with sigma of 1.431
3.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C3(H3), C4(H4), C19(H19), C23(H23), C24(H24), N26(H26),
 C30(H30), C31(H31), C32(H32), C33(H33)
3.c Fitted hexagon refined as free rotating group:
 C6(C7,C2,C3,C4,C5), C19(C20,C23,C24,C25,C18), C34(C29,C30,C31,C32,C33)
3.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C22(H22a,H22b,H22c)
3.e Idealised tetrahedral OH refined as rotating group:
 O16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.2703(4) 0.5862(7) 0.3609(3) 0.055(5) Uani 1 1 d D . . . .
C6 C 0.2533(8) 0.5490(12) 0.6074(5) 0.029(3) Uiso 1 1 d . . . . .
H6 H 0.2720 0.4746 0.6552 0.034 Uiso 1 1 calc R . . . .
C7 C 0.2696(9) 0.5152(11) 0.5281(6) 0.038(3) Uiso 1 1 d G . . . .
H7 H 0.2991 0.4183 0.5228 0.045 Uiso 1 1 calc R . . . .
C2 C 0.2416(8) 0.6263(13) 0.4567(4) 0.022(2) Uiso 1 1 d DG . . . .
C3 C 0.1974(8) 0.7712(12) 0.4646(4) 0.016(2) Uiso 1 1 d G . . . .
H3 H 0.1787 0.8456 0.4169 0.019 Uiso 1 1 calc R . . . .
C4 C 0.1812(8) 0.8050(11) 0.5440(5) 0.016(2) Uiso 1 1 d G . . . .
H4 H 0.1516 0.9019 0.5493 0.019 Uiso 1 1 calc R . . . .
C5 C 0.2091(8) 0.6938(12) 0.6154(4) 0.018(2) Uiso 1 1 d DG . . . .
C8 C 0.2042(14) 0.728(2) 0.7001(9) 0.016(2) Uiso 1 1 d D . . . .
O9 O 0.3345(10) 0.6586(15) 0.7483(6) 0.0237(17) Uiso 1 1 d D . . . .
N10 N 0.0562(13) 0.826(2) 0.7197(8) 0.018(2) Uiso 1 1 d D . . . .
C11 C 0.0607(16) 0.908(2) 0.7834(10) 0.021(2) Uiso 1 1 d D . . . .
C12 C 0.2383(15) 0.893(2) 0.8338(9) 0.018(2) Uiso 1 1 d D . . . .
H12A H 0.2148 0.8296 0.8878 0.026 Uiso 1 1 calc GR . . . .
H12B H 0.2593 0.9875 0.8417 0.026 Uiso 1 1 calc GR . . . .
H12C H 0.3556 0.8519 0.8047 0.026 Uiso 1 1 calc GR . . . .
C13 C -0.1103(17) 1.008(3) 0.7851(12) 0.021(3) Uiso 1 1 d D . . . .
C14 C -0.1623(16) 1.096(3) 0.8400(12) 0.018(3) Uiso 1 1 d D . . . .
H14A H -0.2153 1.1907 0.8077 0.022 Uiso 1 1 calc R . . . .
H14B H -0.0388 1.1093 0.8622 0.022 Uiso 1 1 calc R . . . .
C15 C -0.3116(16) 1.056(3) 0.9150(11) 0.017(3) Uiso 1 1 d D . . . .
O16 O -0.3389(13) 1.132(2) 0.9702(9) 0.039(2) Uiso 1 1 d D . . . .
H16 H -0.4264 1.1006 1.0056 0.059 Uiso 1 1 calc GR . . . .
O17 O -0.3978(10) 0.9455(15) 0.9141(6) 0.0245(17) Uiso 1 1 d D . . . .
O21 O -0.6953(12) 1.0770(18) 0.6082(7) 0.028(2) Uiso 1 1 d D . . . .
C22 C -0.781(2) 1.197(3) 0.6459(12) 0.036(3) Uiso 1 1 d D . . . .
H22A H -0.8913 1.2519 0.6144 0.055 Uiso 1 1 calc GR . . . .
H22B H -0.6803 1.2603 0.6457 0.055 Uiso 1 1 calc GR . . . .
H22C H -0.8299 1.1607 0.7030 0.055 Uiso 1 1 calc GR . . . .
C19 C -0.4237(9) 1.0497(10) 0.7007(4) 0.021(2) Uiso 1 1 d D . . . .
H19 H -0.4902 1.1228 0.7267 0.025 Uiso 1 1 calc R . . . .
C20 C -0.5134(7) 1.0084(10) 0.6376(4) 0.015(2) Uiso 1 1 d DG . . . .
C23 C -0.4140(9) 0.8990(10) 0.5986(4) 0.022(2) Uiso 1 1 d G . . . .
H23 H -0.4740 0.8714 0.5564 0.026 Uiso 1 1 calc R . . . .
C24 C -0.2248(9) 0.8310(10) 0.6227(5) 0.026(3) Uiso 1 1 d G . . . .
H24 H -0.1583 0.7578 0.5966 0.031 Uiso 1 1 calc R . . . .
C25 C -0.1351(7) 0.8722(10) 0.6858(4) 0.014(2) Uiso 1 1 d DG . . . .
C18 C -0.2346(9) 0.9816(10) 0.7247(4) 0.017(2) Uiso 1 1 d DG . . . .
N26 N 0.6239(14) 0.579(2) 0.0711(9) 0.023(2) Uiso 1 1 d D . . . .
H26 H 0.5058 0.6032 0.0522 0.027 Uiso 1 1 calc R . . . .
C27 C 0.751(2) 0.460(4) 0.0539(13) 0.024(3) Uiso 1 1 d D . . . .
O28 O 0.7149(13) 0.385(2) 0.0104(7) 0.025(2) Uiso 1 1 d D . . . .
C34 C 0.9237(6) 0.5479(10) 0.1481(5) 0.019(2) Uiso 1 1 d D . . . .
C29 C 0.9350(6) 0.4449(10) 0.0982(4) 0.018(2) Uiso 1 1 d DG . . . .
C30 C 1.1037(8) 0.3410(10) 0.0982(5) 0.024(2) Uiso 1 1 d G . . . .
H30 H 1.1113 0.2720 0.0648 0.028 Uiso 1 1 calc R . . . .
C31 C 1.2609(6) 0.3401(10) 0.1480(5) 0.019(2) Uiso 1 1 d G . . . .
H31 H 1.3737 0.2705 0.1480 0.023 Uiso 1 1 calc R . . . .
C32 C 1.2496(6) 0.4431(10) 0.1979(4) 0.016(2) Uiso 1 1 d G . . . .
H32 H 1.3548 0.4425 0.2313 0.020 Uiso 1 1 calc R . . . .
C33 C 1.0809(8) 0.5470(10) 0.1980(5) 0.021(2) Uiso 1 1 d G . . . .
H33 H 1.0733 0.6159 0.2314 0.026 Uiso 1 1 calc R . . . .
S35 S 0.7127(4) 0.6725(6) 0.1303(3) 0.030(5) Uani 1 1 d D . . . .
O36 O 0.7668(9) 0.8054(14) 0.0794(6) 0.0254(17) Uiso 1 1 d D . . . .
O37 O 0.5829(10) 0.6783(15) 0.2054(6) 0.0316(19) 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 C2 1.675(10) . ?
C6 H6 0.9300 . ?
C6 C7 1.3900 . ?
C6 C5 1.3900 . ?
C7 H7 0.9300 . ?
C7 C2 1.3900 . ?
C2 C3 1.3900 . ?
C3 H3 0.9300 . ?
C3 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 C8 1.48(2) . ?
C8 O9 1.246(10) . ?
C8 N10 1.33(3) . ?
N10 C11 1.43(4) . ?
N10 C25 1.421(8) . ?
C11 C12 1.484(14) . ?
C11 C13 1.38(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.34(4) . ?
C13 C18 1.43(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.52(2) . ?
C15 O16 1.25(4) . ?
C15 O17 1.27(2) . ?
O16 H16 0.8200 . ?
O21 C22 1.44(4) . ?
O21 C20 1.375(9) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C20 1.3900 . ?
C19 C18 1.3900 . ?
C20 C23 1.3900 . ?
C23 H23 0.9300 . ?
C23 C24 1.3900 . ?
C24 H24 0.9300 . ?
C24 C25 1.3900 . ?
C25 C18 1.3900 . ?
N26 H26 0.8600 . ?
N26 C27 1.38(5) . ?
N26 S35 1.64(3) . ?
C27 O28 1.17(4) . ?
C27 C29 1.462(14) . ?
C34 C29 1.3900 . ?
C34 C33 1.3900 . ?
C34 S35 1.712(7) . ?
C29 C30 1.3900 . ?
C30 H30 0.9300 . ?
C30 C31 1.3900 . ?
C31 H31 0.9300 . ?
C31 C32 1.3900 . ?
C32 H32 0.9300 . ?
C32 C33 1.3900 . ?
C33 H33 0.9300 . ?
S35 O36 1.414(9) . ?
S35 O37 1.439(12) . ?

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 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C2 C7 C6 120.0 . . ?
C2 C7 H7 120.0 . . ?
C7 C2 Cl1 119.9(6) . . ?
C7 C2 C3 120.0 . . ?
C3 C2 Cl1 120.0(6) . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C8 119.0(8) . . ?
C4 C5 C6 120.0 . . ?
C4 C5 C8 120.9(8) . . ?
O9 C8 C5 117.6(18) . . ?
O9 C8 N10 125.1(18) . . ?
N10 C8 C5 117.2(8) . . ?
C8 N10 C11 125.0(10) . . ?
C8 N10 C25 129.8(17) . . ?
C25 N10 C11 105.2(16) . . ?
N10 C11 C12 122(2) . . ?
C13 C11 N10 111.1(13) . . ?
C13 C11 C12 126(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C18 105(2) . . ?
C14 C13 C11 127.2(14) . . ?
C14 C13 C18 126.8(15) . . ?
C13 C14 H14A 107.0 . . ?
C13 C14 H14B 107.0 . . ?
C13 C14 C15 121(2) . . ?
H14A C14 H14B 106.7 . . ?
C15 C14 H14A 107.0 . . ?
C15 C14 H14B 107.0 . . ?
O16 C15 C14 119.7(19) . . ?
O16 C15 O17 126.4(13) . . ?
O17 C15 C14 114(2) . . ?
C15 O16 H16 109.5 . . ?
C20 O21 C22 114.5(13) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C18 C19 H19 120.0 . . ?
O21 C20 C19 122.5(10) . . ?
O21 C20 C23 117.4(10) . . ?
C23 C20 C19 120.0 . . ?
C20 C23 H23 120.0 . . ?
C20 C23 C24 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 N10 131.6(11) . . ?
C24 C25 C18 120.0 . . ?
C18 C25 N10 108.4(11) . . ?
C19 C18 C13 130.3(13) . . ?
C25 C18 C13 109.7(13) . . ?
C25 C18 C19 120.0 . . ?
C27 N26 H26 122.3 . . ?
C27 N26 S35 115.5(11) . . ?
S35 N26 H26 122.3 . . ?
N26 C27 C29 109(3) . . ?
O28 C27 N26 124.5(11) . . ?
O28 C27 C29 127(3) . . ?
C29 C34 C33 120.0 . . ?
C29 C34 S35 111.0(5) . . ?
C33 C34 S35 128.7(5) . . ?
C34 C29 C27 111.5(16) . . ?
C34 C29 C30 120.0 . . ?
C30 C29 C27 128.4(17) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 120.0 . . ?
C33 C32 H32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 H33 120.0 . . ?
N26 S35 C34 92.4(8) . . ?
O36 S35 N26 109.1(6) . . ?
O36 S35 C34 109.7(4) . . ?
O36 S35 O37 118.5(9) . . ?
O37 S35 N26 111.0(6) . . ?
O37 S35 C34 113.1(4) . . ?

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
O16 H16 O17 0.82 1.70 2.514(11) 172.2 2_477
N26 H26 O28 0.86 1.85 2.685(11) 162.0 2_665

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

data_insa_3p33GPa
_database_code_depnum_ccdc_archive 'CCDC 1902712'
loop_
_audit_author_name
_audit_author_address
'Iain Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-06-11 downloaded from the CCDC.
;
_audit_creation_date             2019-02-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'?1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid 1,2-benzisothiazol-3(2H)-one 1,1-dioxide'
_chemical_formula_moiety         'C19 H16 Cl N O4, C7 H5 N O3 S'
_chemical_formula_sum            'C26 H21 Cl N2 O7 S'
_chemical_formula_weight         540.96
_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'
S S 0.1246 0.1234 '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                   6.7888(3)
_cell_length_b                   9.6045(11)
_cell_length_c                   16.3703(16)
_cell_angle_alpha                77.764(8)
_cell_angle_beta                 84.858(6)
_cell_angle_gamma                81.297(8)
_cell_volume                     1029.30(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1371
_cell_measurement_temperature    297
_cell_measurement_theta_max      22.422
_cell_measurement_theta_min      3.227
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.918
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0729 before and 0.0488 after correction. The Ratio of minimum to maximum transmission is 0.9098. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Recrystallised from a 1:1 molar ratio of indomethacin and saccharin from ethyl acetate'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.314
_diffrn_reflns_Laue_measured_fraction_max 0.314
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4793
_diffrn_reflns_point_group_measured_fraction_full 0.314
_diffrn_reflns_point_group_measured_fraction_max 0.314
_diffrn_reflns_theta_full        23.324
_diffrn_reflns_theta_max         23.324
_diffrn_reflns_theta_min         3.041
_diffrn_ambient_temperature      297.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.314
_diffrn_measured_fraction_theta_max 0.314
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          'High pressure dataset at 3.33 GPa'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                747
_reflns_number_total             941
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         941
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      1.088
_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)+(0.0584P)²+5.4456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1627
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C2-Cl1
 0.011 with sigma of 1.742
 C5-C8
 0.011 with sigma of 1.495
 O9-C8
 0.013 with sigma of 1.217
 C8-N10
 0.021 with sigma of 1.413
 C11-N10
 0.018 with sigma of 1.398
 C25-N10
 0.015 with sigma of 1.415
 C12-C11
 0.01 with sigma of 1.491
 C11-C13
 0.007 with sigma of 1.355
 C14-C13
 0.009 with sigma of 1.502
 C18-C13
 0.015 with sigma of 1.437
 C14-C15
 0.008 with sigma of 1.506
 O16-C15
 0.023 with sigma of 1.307
 O17-C15
 0.021 with sigma of 1.213
 C19-C18
 0.012 with sigma of 1.395
 C18-C25
 0.01 with sigma of 1.406
 O21-C20
 0.011 with sigma of 1.369
 O21-C22
 0.015 with sigma of 1.425
 C27-N26
 0.013 with sigma of 1.374
 S35-N26
 0.015 with sigma of 1.654
 O28-C27
 0.011 with sigma of 1.228
 C29-C27
 0.012 with sigma of 1.483
 C34-S35
 0.008 with sigma of 1.753
 O36-S35
 0.007 with sigma of 1.431
 O37-S35
 0.007 with sigma of 1.431
3.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C3(H3), C23(H23), C24(H24), C19(H19), N26(H26),
 C30(H30), C31(H31), C32(H32), C33(H33)
3.c Fitted hexagon refined as free rotating group:
 C4(C5,C6,C7,C2,C3), C23(C24,C25,C18,C19,C20), C34(C29,C30,C31,C32,C33)
3.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C22(H22a,H22b,H22c)
3.e Idealised tetrahedral OH refined as rotating group:
 O16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.2696(4) 0.5861(7) 0.3632(2) 0.060(5) Uani 1 1 d D . . . .
C4 C 0.1855(8) 0.8043(11) 0.5451(5) 0.019(2) Uiso 1 1 d . . . . .
H4 H 0.1581 0.9001 0.5502 0.023 Uiso 1 1 calc R . . . .
C5 C 0.2095(8) 0.6962(12) 0.6163(4) 0.019(2) Uiso 1 1 d DG . . . .
C6 C 0.2504(8) 0.5531(11) 0.6087(4) 0.032(3) Uiso 1 1 d G . . . .
H6 H 0.2664 0.4807 0.6563 0.038 Uiso 1 1 calc R . . . .
C7 C 0.2673(9) 0.5181(11) 0.5300(5) 0.042(3) Uiso 1 1 d G . . . .
H7 H 0.2946 0.4224 0.5249 0.050 Uiso 1 1 calc R . . . .
C2 C 0.2432(8) 0.6263(12) 0.4588(4) 0.023(2) Uiso 1 1 d DG . . . .
C3 C 0.2024(8) 0.7694(12) 0.4664(4) 0.019(2) Uiso 1 1 d G . . . .
H3 H 0.1863 0.8417 0.4188 0.023 Uiso 1 1 calc R . . . .
C8 C 0.2023(14) 0.730(2) 0.7010(8) 0.017(2) Uiso 1 1 d D . . . .
O9 O 0.3305(9) 0.6636(15) 0.7494(6) 0.0267(17) Uiso 1 1 d D . . . .
N10 N 0.0567(13) 0.8311(19) 0.7206(7) 0.019(2) Uiso 1 1 d D . . . .
C11 C 0.0606(15) 0.911(2) 0.7850(9) 0.022(2) Uiso 1 1 d D . . . .
C12 C 0.2364(14) 0.895(2) 0.8347(9) 0.018(2) Uiso 1 1 d D . . . .
H12A H 0.2115 0.8365 0.8890 0.027 Uiso 1 1 calc GR . . . .
H12B H 0.2617 0.9874 0.8407 0.027 Uiso 1 1 calc GR . . . .
H12C H 0.3504 0.8487 0.8067 0.027 Uiso 1 1 calc GR . . . .
C13 C -0.1077(16) 1.003(3) 0.7855(11) 0.024(3) Uiso 1 1 d D . . . .
C14 C -0.1635(16) 1.096(3) 0.8412(11) 0.018(3) Uiso 1 1 d D . . . .
H14A H -0.2201 1.1885 0.8091 0.022 Uiso 1 1 calc R . . . .
H14B H -0.0431 1.1115 0.8639 0.022 Uiso 1 1 calc R . . . .
C15 C -0.3103(16) 1.052(3) 0.9140(10) 0.022(3) Uiso 1 1 d D . . . .
O16 O -0.3448(12) 1.1338(19) 0.9706(8) 0.038(2) Uiso 1 1 d D . . . .
H16 H -0.4342 1.1060 1.0044 0.057 Uiso 1 1 calc GR . . . .
O17 O -0.3931(10) 0.9447(14) 0.9147(6) 0.0277(17) Uiso 1 1 d D . . . .
O21 O -0.6899(12) 1.0743(17) 0.6083(7) 0.031(2) Uiso 1 1 d D . . . .
C22 C -0.7801(19) 1.196(3) 0.6474(11) 0.035(3) Uiso 1 1 d D . . . .
H22A H -0.8943 1.2464 0.6179 0.052 Uiso 1 1 calc GR . . . .
H22B H -0.6838 1.2611 0.6448 0.052 Uiso 1 1 calc GR . . . .
H22C H -0.8206 1.1611 0.7048 0.052 Uiso 1 1 calc GR . . . .
C23 C -0.4106(9) 0.9010(10) 0.6000(4) 0.021(2) Uiso 1 1 d . . . . .
H23 H -0.4703 0.8734 0.5581 0.025 Uiso 1 1 calc R . . . .
C24 C -0.2222(9) 0.8342(9) 0.6236(4) 0.026(2) Uiso 1 1 d G . . . .
H24 H -0.1559 0.7619 0.5975 0.032 Uiso 1 1 calc R . . . .
C25 C -0.1330(7) 0.8755(9) 0.6862(4) 0.014(2) Uiso 1 1 d DG . . . .
C18 C -0.2321(9) 0.9837(10) 0.7252(4) 0.016(2) Uiso 1 1 d DG . . . .
C19 C -0.4205(9) 1.0505(9) 0.7016(4) 0.023(2) Uiso 1 1 d DG . . . .
H19 H -0.4869 1.1228 0.7277 0.027 Uiso 1 1 calc R . . . .
C20 C -0.5098(7) 1.0092(10) 0.6390(4) 0.020(2) Uiso 1 1 d DG . . . .
N26 N 0.6254(13) 0.581(2) 0.0712(9) 0.024(2) Uiso 1 1 d D . . . .
H26 H 0.5092 0.6061 0.0515 0.029 Uiso 1 1 calc R . . . .
C27 C 0.7500(19) 0.465(3) 0.0548(12) 0.023(3) Uiso 1 1 d D . . . .
O28 O 0.7167(13) 0.3857(19) 0.0103(7) 0.0271(19) Uiso 1 1 d D . . . .
C34 C 0.9253(6) 0.5466(9) 0.1475(5) 0.016(2) Uiso 1 1 d D . . . .
C29 C 0.9347(6) 0.4439(10) 0.0983(4) 0.018(2) Uiso 1 1 d DG . . . .
C30 C 1.1012(8) 0.3400(9) 0.0984(4) 0.024(2) Uiso 1 1 d G . . . .
H30 H 1.1075 0.2713 0.0655 0.029 Uiso 1 1 calc R . . . .
C31 C 1.2582(6) 0.3387(9) 0.1476(5) 0.021(2) Uiso 1 1 d G . . . .
H31 H 1.3696 0.2692 0.1476 0.025 Uiso 1 1 calc R . . . .
C32 C 1.2488(6) 0.4413(10) 0.1968(4) 0.017(2) Uiso 1 1 d G . . . .
H32 H 1.3539 0.4405 0.2297 0.021 Uiso 1 1 calc R . . . .
C33 C 1.0823(8) 0.5453(9) 0.1968(4) 0.024(2) Uiso 1 1 d G . . . .
H33 H 1.0760 0.6139 0.2297 0.029 Uiso 1 1 calc R . . . .
S35 S 0.7132(4) 0.6706(6) 0.1313(2) 0.031(5) Uani 1 1 d D . . . .
O36 O 0.7652(10) 0.8013(14) 0.0821(6) 0.0304(17) Uiso 1 1 d D . . . .
O37 O 0.5848(10) 0.6747(14) 0.2060(6) 0.0349(19) 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 C2 1.678(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C4 C3 1.3900 . ?
C5 C6 1.3900 . ?
C5 C8 1.49(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C2 1.3900 . ?
C2 C3 1.3900 . ?
C3 H3 0.9300 . ?
C8 O9 1.239(10) . ?
C8 N10 1.34(3) . ?
N10 C11 1.44(3) . ?
N10 C25 1.421(8) . ?
C11 C12 1.473(13) . ?
C11 C13 1.33(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.40(4) . ?
C13 C18 1.413(19) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.514(19) . ?
C15 O16 1.32(3) . ?
C15 O17 1.25(2) . ?
O16 H16 0.8200 . ?
O21 C22 1.48(4) . ?
O21 C20 1.372(9) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C24 1.3900 . ?
C23 C20 1.3900 . ?
C24 H24 0.9300 . ?
C24 C25 1.3900 . ?
C25 C18 1.3900 . ?
C18 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C20 1.3900 . ?
N26 H26 0.8600 . ?
N26 C27 1.35(5) . ?
N26 S35 1.64(2) . ?
C27 O28 1.22(4) . ?
C27 C29 1.464(12) . ?
C34 C29 1.3900 . ?
C34 C33 1.3900 . ?
C34 S35 1.725(7) . ?
C29 C30 1.3900 . ?
C30 H30 0.9300 . ?
C30 C31 1.3900 . ?
C31 H31 0.9300 . ?
C31 C32 1.3900 . ?
C32 H32 0.9300 . ?
C32 C33 1.3900 . ?
C33 H33 0.9300 . ?
S35 O36 1.415(9) . ?
S35 O37 1.440(12) . ?

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
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 C8 121.3(8) . . ?
C6 C5 C8 118.6(8) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C2 C7 C6 120.0 . . ?
C2 C7 H7 120.0 . . ?
C7 C2 Cl1 120.5(5) . . ?
C3 C2 Cl1 119.4(5) . . ?
C3 C2 C7 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
O9 C8 C5 118.0(17) . . ?
O9 C8 N10 124.0(18) . . ?
N10 C8 C5 118.0(8) . . ?
C8 N10 C11 125.6(9) . . ?
C8 N10 C25 128.2(16) . . ?
C25 N10 C11 106.2(15) . . ?
N10 C11 C12 121.8(19) . . ?
C13 C11 N10 108.8(13) . . ?
C13 C11 C12 129(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 126.2(14) . . ?
C11 C13 C18 109(2) . . ?
C14 C13 C18 124.1(15) . . ?
C13 C14 H14A 107.8 . . ?
C13 C14 H14B 107.8 . . ?
C13 C14 C15 118(2) . . ?
H14A C14 H14B 107.1 . . ?
C15 C14 H14A 107.8 . . ?
C15 C14 H14B 107.8 . . ?
O16 C15 C14 117.1(19) . . ?
O17 C15 C14 118(2) . . ?
O17 C15 O16 125.0(13) . . ?
C15 O16 H16 109.5 . . ?
C20 O21 C22 113.3(13) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 H23 120.0 . . ?
C24 C23 C20 120.0 . . ?
C20 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 N10 132.3(10) . . ?
C18 C25 N10 107.6(10) . . ?
C18 C25 C24 120.0 . . ?
C25 C18 C13 107.8(13) . . ?
C25 C18 C19 120.0 . . ?
C19 C18 C13 132.2(13) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
O21 C20 C23 115.8(10) . . ?
O21 C20 C19 124.1(10) . . ?
C19 C20 C23 120.0 . . ?
C27 N26 H26 122.6 . . ?
C27 N26 S35 114.8(11) . . ?
S35 N26 H26 122.6 . . ?
N26 C27 C29 111(3) . . ?
O28 C27 N26 125.7(11) . . ?
O28 C27 C29 123(3) . . ?
C29 C34 C33 120.0 . . ?
C29 C34 S35 111.3(5) . . ?
C33 C34 S35 128.5(5) . . ?
C34 C29 C27 109.6(16) . . ?
C30 C29 C27 130.4(16) . . ?
C30 C29 C34 120.0 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 120.0 . . ?
C31 C32 C33 120.0 . . ?
C33 C32 H32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 H33 120.0 . . ?
N26 S35 C34 92.4(8) . . ?
O36 S35 N26 109.0(6) . . ?
O36 S35 C34 109.4(4) . . ?
O36 S35 O37 119.0(9) . . ?
O37 S35 N26 110.5(6) . . ?
O37 S35 C34 113.3(4) . . ?

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
C12 H12C O9 0.96 2.21 2.83(2) 121.6 .
O16 H16 O17 0.82 1.73 2.543(10) 172.4 2_477
N26 H26 O28 0.86 1.89 2.725(11) 161.9 2_665

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

data_insa_4p06GPa
_database_code_depnum_ccdc_archive 'CCDC 1902713'
loop_
_audit_author_name
_audit_author_address
'Iain Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-06-11 downloaded from the CCDC.
;
_audit_creation_date             2018-06-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid 1,2-benzisothiazol-3(2H)-one 1,1-dioxide'
_chemical_formula_moiety         'C19 H16 Cl N O4, C7 H5 N O3 S'
_chemical_formula_sum            'C26 H21 Cl N2 O7 S'
_chemical_formula_weight         540.96
_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'
S S 0.1246 0.1234 '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                   6.7561(3)
_cell_length_b                   9.5308(11)
_cell_length_c                   16.3385(16)
_cell_angle_alpha                77.508(8)
_cell_angle_beta                 84.710(6)
_cell_angle_gamma                81.556(8)
_cell_volume                     1014.02(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1341
_cell_measurement_temperature    297
_cell_measurement_theta_max      23.070
_cell_measurement_theta_min      3.237
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.917
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0696 before and 0.0508 after correction. The Ratio of minimum to maximum transmission is 0.9264. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Recrystallised in 1:1 molar ratio of indomethacin and saccharin from ethyl acetate'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.314
_diffrn_reflns_Laue_measured_fraction_max 0.314
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4707
_diffrn_reflns_point_group_measured_fraction_full 0.314
_diffrn_reflns_point_group_measured_fraction_max 0.314
_diffrn_reflns_theta_full        23.293
_diffrn_reflns_theta_max         23.293
_diffrn_reflns_theta_min         3.054
_diffrn_ambient_temperature      297.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.314
_diffrn_measured_fraction_theta_max 0.314
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          'High pressure dataset at 4.06 GPa'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                731
_reflns_number_total             921
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         921
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0638
_refine_ls_restrained_S_all      1.071
_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)+(0.0602P)²+4.9631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1569
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C2-Cl1
 0.011 with sigma of 1.742
 C5-C8
 0.011 with sigma of 1.495
 O9-C8
 0.013 with sigma of 1.217
 C8-N10
 0.021 with sigma of 1.413
 C11-N10
 0.018 with sigma of 1.398
 C25-N10
 0.015 with sigma of 1.415
 C12-C11
 0.01 with sigma of 1.491
 C11-C13
 0.007 with sigma of 1.355
 C14-C13
 0.009 with sigma of 1.502
 C18-C13
 0.015 with sigma of 1.437
 C14-C15
 0.008 with sigma of 1.506
 O16-C15
 0.023 with sigma of 1.307
 O17-C15
 0.021 with sigma of 1.213
 C19-C18
 0.012 with sigma of 1.395
 C18-C25
 0.01 with sigma of 1.406
 O21-C20
 0.011 with sigma of 1.369
 O21-C22
 0.015 with sigma of 1.425
 C27-N26
 0.013 with sigma of 1.374
 S35-N26
 0.015 with sigma of 1.654
 O28-C27
 0.011 with sigma of 1.228
 C29-C27
 0.012 with sigma of 1.483
 C34-S35
 0.008 with sigma of 1.753
 O36-S35
 0.007 with sigma of 1.431
 O37-S35
 0.007 with sigma of 1.431
3.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C3(H3), C23(H23), C24(H24), C19(H19), N26(H26),
 C30(H30), C31(H31), C32(H32), C33(H33)
3.c Fitted hexagon refined as free rotating group:
 C4(C5,C6,C7,C2,C3), C23(C24,C25,C18,C19,C20), C34(C29,C30,C31,C32,C33)
3.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C22(H22a,H22b,H22c)
3.e Idealised tetrahedral OH refined as rotating group:
 O16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.2699(4) 0.5859(7) 0.3622(2) 0.052(5) Uani 1 1 d D . . . .
C4 C 0.1834(8) 0.8061(11) 0.5449(5) 0.017(2) Uiso 1 1 d . . . . .
H4 H 0.1553 0.9024 0.5500 0.020 Uiso 1 1 calc R . . . .
C5 C 0.2091(8) 0.6968(12) 0.6163(4) 0.020(2) Uiso 1 1 d DG . . . .
C6 C 0.2512(8) 0.5528(11) 0.6087(4) 0.030(3) Uiso 1 1 d G . . . .
H6 H 0.2683 0.4798 0.6565 0.037 Uiso 1 1 calc R . . . .
C7 C 0.2676(8) 0.5181(11) 0.5298(5) 0.040(3) Uiso 1 1 d G . . . .
H7 H 0.2958 0.4217 0.5247 0.048 Uiso 1 1 calc R . . . .
C2 C 0.2420(8) 0.6273(12) 0.4585(4) 0.020(2) Uiso 1 1 d DG . . . .
C3 C 0.1999(8) 0.7713(12) 0.4660(4) 0.018(2) Uiso 1 1 d G . . . .
H3 H 0.1827 0.8444 0.4183 0.021 Uiso 1 1 calc R . . . .
C8 C 0.2030(14) 0.728(2) 0.7011(8) 0.018(2) Uiso 1 1 d D . . . .
O9 O 0.3322(9) 0.6614(15) 0.7489(6) 0.0278(17) Uiso 1 1 d D . . . .
N10 N 0.0557(12) 0.8317(19) 0.7208(7) 0.018(2) Uiso 1 1 d D . . . .
C11 C 0.0616(15) 0.910(2) 0.7847(9) 0.020(2) Uiso 1 1 d D . . . .
C12 C 0.2372(14) 0.894(2) 0.8343(9) 0.021(2) Uiso 1 1 d D . . . .
H12A H 0.2083 0.8421 0.8904 0.031 Uiso 1 1 calc GR . . . .
H12B H 0.2684 0.9884 0.8362 0.031 Uiso 1 1 calc GR . . . .
H12C H 0.3497 0.8418 0.8087 0.031 Uiso 1 1 calc GR . . . .
C13 C -0.1090(16) 1.006(3) 0.7858(11) 0.023(3) Uiso 1 1 d D . . . .
C14 C -0.1636(16) 1.098(3) 0.8411(11) 0.021(3) Uiso 1 1 d D . . . .
H14A H -0.2189 1.1910 0.8089 0.025 Uiso 1 1 calc R . . . .
H14B H -0.0423 1.1125 0.8638 0.025 Uiso 1 1 calc R . . . .
C15 C -0.3118(15) 1.055(2) 0.9144(10) 0.018(3) Uiso 1 1 d D . . . .
O16 O -0.3423(12) 1.133(2) 0.9706(8) 0.040(2) Uiso 1 1 d D . . . .
H16 H -0.4294 1.1031 1.0056 0.060 Uiso 1 1 calc GR . . . .
O17 O -0.3947(10) 0.9437(14) 0.9146(6) 0.0277(17) Uiso 1 1 d D . . . .
O21 O -0.6916(12) 1.0741(17) 0.6082(7) 0.031(2) Uiso 1 1 d D . . . .
C22 C -0.7785(19) 1.195(3) 0.6453(11) 0.032(3) Uiso 1 1 d D . . . .
H22A H -0.8882 1.2487 0.6136 0.047 Uiso 1 1 calc GR . . . .
H22B H -0.6787 1.2577 0.6448 0.047 Uiso 1 1 calc GR . . . .
H22C H -0.8263 1.1604 0.7022 0.047 Uiso 1 1 calc GR . . . .
C23 C -0.4118(9) 0.8991(10) 0.5993(4) 0.021(2) Uiso 1 1 d . . . . .
H23 H -0.4717 0.8712 0.5574 0.025 Uiso 1 1 calc R . . . .
C24 C -0.2230(9) 0.8318(9) 0.6231(4) 0.028(3) Uiso 1 1 d G . . . .
H24 H -0.1567 0.7589 0.5971 0.033 Uiso 1 1 calc R . . . .
C25 C -0.1334(7) 0.8735(9) 0.6857(4) 0.016(2) Uiso 1 1 d DG . . . .
C18 C -0.2325(9) 0.9825(10) 0.7245(4) 0.015(2) Uiso 1 1 d DG . . . .
C19 C -0.4213(9) 1.0497(9) 0.7008(4) 0.023(2) Uiso 1 1 d DG . . . .
H19 H -0.4876 1.1227 0.7267 0.028 Uiso 1 1 calc R . . . .
C20 C -0.5109(7) 1.0080(10) 0.6381(4) 0.016(2) Uiso 1 1 d DG . . . .
N26 N 0.6247(13) 0.583(2) 0.0716(9) 0.023(2) Uiso 1 1 d D . . . .
H26 H 0.5076 0.6080 0.0523 0.028 Uiso 1 1 calc R . . . .
C27 C 0.7523(18) 0.461(3) 0.0537(12) 0.021(3) Uiso 1 1 d D . . . .
O28 O 0.7146(12) 0.3866(18) 0.0105(7) 0.0237(19) Uiso 1 1 d D . . . .
C34 C 0.9245(6) 0.5477(9) 0.1479(4) 0.015(2) Uiso 1 1 d D . . . .
C29 C 0.9346(6) 0.4449(10) 0.0983(4) 0.016(2) Uiso 1 1 d DG . . . .
C30 C 1.1019(8) 0.3408(9) 0.0983(4) 0.025(2) Uiso 1 1 d G . . . .
H30 H 1.1086 0.2720 0.0652 0.030 Uiso 1 1 calc R . . . .
C31 C 1.2590(6) 0.3395(9) 0.1478(4) 0.019(2) Uiso 1 1 d G . . . .
H31 H 1.3709 0.2698 0.1478 0.022 Uiso 1 1 calc R . . . .
C32 C 1.2489(6) 0.4422(10) 0.1974(4) 0.017(2) Uiso 1 1 d G . . . .
H32 H 1.3541 0.4414 0.2305 0.020 Uiso 1 1 calc R . . . .
C33 C 1.0817(8) 0.5463(9) 0.1974(4) 0.024(2) Uiso 1 1 d G . . . .
H33 H 1.0749 0.6151 0.2305 0.028 Uiso 1 1 calc R . . . .
S35 S 0.7131(4) 0.6712(6) 0.1309(2) 0.025(5) Uani 1 1 d D . . . .
O36 O 0.7658(9) 0.8034(14) 0.0808(6) 0.0273(17) Uiso 1 1 d D . . . .
O37 O 0.5844(10) 0.6745(14) 0.2056(6) 0.0323(18) 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 C2 1.690(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C4 C3 1.3900 . ?
C5 C6 1.3900 . ?
C5 C8 1.48(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C2 1.3900 . ?
C2 C3 1.3900 . ?
C3 H3 0.9300 . ?
C8 O9 1.236(10) . ?
C8 N10 1.36(3) . ?
N10 C11 1.41(3) . ?
N10 C25 1.416(8) . ?
C11 C12 1.470(13) . ?
C11 C13 1.36(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.38(4) . ?
C13 C18 1.43(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.514(19) . ?
C15 O16 1.29(3) . ?
C15 O17 1.27(2) . ?
O16 H16 0.8200 . ?
O21 C22 1.44(4) . ?
O21 C20 1.371(9) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C24 1.3900 . ?
C23 C20 1.3900 . ?
C24 H24 0.9300 . ?
C24 C25 1.3900 . ?
C25 C18 1.3900 . ?
C18 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C20 1.3900 . ?
N26 H26 0.8600 . ?
N26 C27 1.40(5) . ?
N26 S35 1.62(2) . ?
C27 O28 1.17(4) . ?
C27 C29 1.460(12) . ?
C34 C29 1.3900 . ?
C34 C33 1.3900 . ?
C34 S35 1.715(7) . ?
C29 C30 1.3900 . ?
C30 H30 0.9300 . ?
C30 C31 1.3900 . ?
C31 H31 0.9300 . ?
C31 C32 1.3900 . ?
C32 H32 0.9300 . ?
C32 C33 1.3900 . ?
C33 H33 0.9300 . ?
S35 O36 1.420(9) . ?
S35 O37 1.436(12) . ?

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
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C8 122.1(8) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C8 117.8(8) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C2 120.0 . . ?
C2 C7 H7 120.0 . . ?
C7 C2 Cl1 120.1(5) . . ?
C3 C2 Cl1 119.9(5) . . ?
C3 C2 C7 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
O9 C8 C5 118.3(17) . . ?
O9 C8 N10 124.4(18) . . ?
N10 C8 C5 117.3(8) . . ?
C8 N10 C11 125.0(9) . . ?
C8 N10 C25 126.8(16) . . ?
C11 N10 C25 108.0(15) . . ?
N10 C11 C12 123(2) . . ?
C13 C11 N10 109.1(13) . . ?
C13 C11 C12 128(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 127.0(14) . . ?
C11 C13 C18 107(2) . . ?
C14 C13 C18 125.7(14) . . ?
C13 C14 H14A 107.6 . . ?
C13 C14 H14B 107.6 . . ?
C13 C14 C15 119(2) . . ?
H14A C14 H14B 107.1 . . ?
C15 C14 H14A 107.6 . . ?
C15 C14 H14B 107.6 . . ?
O16 C15 C14 117.7(19) . . ?
O17 C15 C14 116(2) . . ?
O17 C15 O16 125.9(12) . . ?
C15 O16 H16 109.5 . . ?
C20 O21 C22 114.0(13) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 H23 120.0 . . ?
C24 C23 C20 120.0 . . ?
C20 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 N10 133.5(10) . . ?
C18 C25 N10 106.5(10) . . ?
C18 C25 C24 120.0 . . ?
C25 C18 C13 109.2(12) . . ?
C25 C18 C19 120.0 . . ?
C19 C18 C13 130.8(12) . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0 . . ?
C20 C19 H19 120.0 . . ?
O21 C20 C23 116.5(9) . . ?
O21 C20 C19 123.5(9) . . ?
C19 C20 C23 120.0 . . ?
C27 N26 H26 122.3 . . ?
C27 N26 S35 115.3(10) . . ?
S35 N26 H26 122.3 . . ?
N26 C27 C29 109(3) . . ?
O28 C27 N26 124.6(10) . . ?
O28 C27 C29 127(3) . . ?
C29 C34 C33 120.0 . . ?
C29 C34 S35 110.9(5) . . ?
C33 C34 S35 128.9(5) . . ?
C34 C29 C27 111.5(15) . . ?
C30 C29 C27 128.5(15) . . ?
C30 C29 C34 120.0 . . ?
C29 C30 H30 120.0 . . ?
C29 C30 C31 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 120.0 . . ?
C31 C32 C33 120.0 . . ?
C33 C32 H32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 H33 120.0 . . ?
N26 S35 C34 93.0(8) . . ?
O36 S35 N26 108.8(6) . . ?
O36 S35 C34 109.5(4) . . ?
O36 S35 O37 119.3(9) . . ?
O37 S35 N26 110.2(6) . . ?
O37 S35 C34 112.8(4) . . ?

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
C12 H12C O9 0.96 2.18 2.83(3) 124.7 .
O16 H16 O17 0.82 1.71 2.527(10) 172.8 2_477
N26 H26 O28 0.86 1.88 2.708(10) 160.2 2_665

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

data_insa_1p66GPa
_database_code_depnum_ccdc_archive 'CCDC 1902711'
loop_
_audit_author_name
_audit_author_address
'Iain Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-06-11 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     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid 1,2-benzisothiazol-3(2H)-one 1,1-dioxide'
_chemical_formula_moiety         'C19 H16 Cl N O4, C7 H5 N O3 S'
_chemical_formula_sum            'C26 H21 Cl N2 O7 S'
_chemical_formula_weight         540.96
_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'
S S 0.1246 0.1234 '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                   6.9301(4)
_cell_length_b                   9.9420(7)
_cell_length_c                   16.514(3)
_cell_angle_alpha                79.013(11)
_cell_angle_beta                 85.441(10)
_cell_angle_gamma                80.339(5)
_cell_volume                     1099.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1037
_cell_measurement_temperature    297
_cell_measurement_theta_max      21.250
_cell_measurement_theta_min      2.256
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.5863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0861 before and 0.0545 after correction. The Ratio of minimum to maximum transmission is 0.7871. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Recrystallisation of 1:1 molar ratio of indomethacin and saccharin in ethyl acetate'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_Laue_measured_fraction_full 0.330
_diffrn_reflns_Laue_measured_fraction_max 0.330
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            5514
_diffrn_reflns_point_group_measured_fraction_full 0.330
_diffrn_reflns_point_group_measured_fraction_max 0.330
_diffrn_reflns_theta_full        23.262
_diffrn_reflns_theta_max         23.262
_diffrn_reflns_theta_min         2.255
_diffrn_ambient_temperature      297
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.330
_diffrn_measured_fraction_theta_max 0.330
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          
'High pressure dataset at 1.66 GPa ona new crystal from previous datasets'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                761
_reflns_number_total             1044
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1044
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.084
_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)+(0.0376P)²+4.6151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1487
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C2-Cl1
 0.011 with sigma of 1.742
 C5-C8
 0.011 with sigma of 1.495
 O9-C8
 0.013 with sigma of 1.217
 C8-N10
 0.021 with sigma of 1.413
 C11-N10
 0.018 with sigma of 1.398
 C25-N10
 0.015 with sigma of 1.415
 C12-C11
 0.01 with sigma of 1.491
 C11-C13
 0.007 with sigma of 1.355
 C14-C13
 0.009 with sigma of 1.502
 C18-C13
 0.015 with sigma of 1.437
 C14-C15
 0.008 with sigma of 1.506
 O16-C15
 0.023 with sigma of 1.307
 O17-C15
 0.021 with sigma of 1.213
 C19-C18
 0.012 with sigma of 1.395
 C18-C25
 0.01 with sigma of 1.406
 O21-C20
 0.011 with sigma of 1.369
 O21-C22
 0.015 with sigma of 1.425
 C27-N26
 0.013 with sigma of 1.374
 S35-N26
 0.015 with sigma of 1.654
 O28-C27
 0.011 with sigma of 1.228
 C29-C27
 0.012 with sigma of 1.483
 C34-S35
 0.008 with sigma of 1.753
 O36-S35
 0.007 with sigma of 1.431
 O37-S35
 0.007 with sigma of 1.431
3.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C3(H3), C23(H23), C24(H24), C19(H19), N26(H26),
 C30(H30), C31(H31), C32(H32), C33(H33)
3.c Fitted hexagon refined as free rotating group:
 C4(C5,C6,C7,C2,C3), C23(C24,C25,C18,C19,C20), C34(C29,C30,C31,C32,C33)
3.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C22(H22a,H22b,H22c)
3.e Idealised tetrahedral OH refined as rotating group:
 O16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.2699(5) 0.5879(3) 0.3674(6) 0.084(6) Uani 1 1 d D . . . .
C4 C 0.1894(7) 0.8046(4) 0.5485(8) 0.026(2) Uiso 1 1 d . . . . .
H4 H 0.1648 0.8972 0.5545 0.031 Uiso 1 1 calc R . . . .
C5 C 0.2083(9) 0.7004(7) 0.6180(7) 0.027(3) Uiso 1 1 d DG . . . .
C6 C 0.2451(8) 0.5621(5) 0.6092(8) 0.040(3) Uiso 1 1 d G . . . .
H6 H 0.2577 0.4924 0.6557 0.048 Uiso 1 1 calc R . . . .
C7 C 0.2631(8) 0.5278(4) 0.5309(8) 0.046(3) Uiso 1 1 d G . . . .
H7 H 0.2878 0.4353 0.5250 0.055 Uiso 1 1 calc R . . . .
C2 C 0.2443(10) 0.6320(7) 0.4614(7) 0.043(3) Uiso 1 1 d DG . . . .
C3 C 0.2074(8) 0.7704(6) 0.4702(7) 0.033(3) Uiso 1 1 d G . . . .
H3 H 0.1948 0.8401 0.4237 0.040 Uiso 1 1 calc R . . . .
C8 C 0.2001(13) 0.7332(8) 0.6977(15) 0.026(2) Uiso 1 1 d D . . . .
O9 O 0.3189(9) 0.6733(6) 0.7541(10) 0.0433(19) Uiso 1 1 d D . . . .
N10 N 0.0531(10) 0.8378(6) 0.7237(11) 0.0259(19) Uiso 1 1 d D . . . .
C11 C 0.0597(12) 0.9140(7) 0.7842(14) 0.022(2) Uiso 1 1 d D . . . .
C12 C 0.2332(12) 0.8991(9) 0.8364(13) 0.030(2) Uiso 1 1 d D . . . .
H12A H 0.2346 0.8178 0.8785 0.045 Uiso 1 1 calc GR . . . .
H12B H 0.2238 0.9794 0.8618 0.045 Uiso 1 1 calc GR . . . .
H12C H 0.3518 0.8908 0.8023 0.045 Uiso 1 1 calc GR . . . .
C13 C -0.1097(11) 1.0036(7) 0.7876(12) 0.019(2) Uiso 1 1 d D . . . .
C14 C -0.1676(12) 1.0992(8) 0.8487(14) 0.026(2) Uiso 1 1 d D . . . .
H14A H -0.0506 1.1101 0.8737 0.032 Uiso 1 1 calc R . . . .
H14B H -0.2231 1.1897 0.8191 0.032 Uiso 1 1 calc R . . . .
C15 C -0.3101(12) 1.0524(8) 0.9149(14) 0.025(2) Uiso 1 1 d D . . . .
O16 O -0.3541(9) 1.1332(6) 0.9683(10) 0.0414(19) Uiso 1 1 d D . . . .
H16 H -0.4394 1.1049 1.0013 0.062 Uiso 1 1 calc GR . . . .
O17 O -0.3858(8) 0.9473(5) 0.9177(9) 0.0279(16) Uiso 1 1 d D . . . .
O21 O -0.6816(8) 1.0731(5) 0.6114(9) 0.0384(18) Uiso 1 1 d D . . . .
C22 C -0.7765(13) 1.1898(8) 0.6446(14) 0.039(3) Uiso 1 1 d D . . . .
H22A H -0.8920 1.2305 0.6150 0.058 Uiso 1 1 calc GR . . . .
H22B H -0.6893 1.2568 0.6393 0.058 Uiso 1 1 calc GR . . . .
H22C H -0.8126 1.1612 0.7018 0.058 Uiso 1 1 calc GR . . . .
C23 C -0.4058(8) 0.9064(5) 0.6011(6) 0.030(2) Uiso 1 1 d . . . . .
H23 H -0.4645 0.8794 0.5594 0.035 Uiso 1 1 calc R . . . .
C24 C -0.2198(7) 0.8411(5) 0.6244(6) 0.032(2) Uiso 1 1 d G . . . .
H24 H -0.1542 0.7704 0.5982 0.038 Uiso 1 1 calc R . . . .
C25 C -0.1320(6) 0.8815(5) 0.6867(6) 0.026(2) Uiso 1 1 d DG . . . .
C18 C -0.2301(8) 0.9871(5) 0.7259(6) 0.019(2) Uiso 1 1 d DG . . . .
C19 C -0.4160(7) 1.0524(5) 0.7026(6) 0.025(2) Uiso 1 1 d DG . . . .
H19 H -0.4816 1.1231 0.7288 0.029 Uiso 1 1 calc R . . . .
C20 C -0.5039(6) 1.0121(5) 0.6402(6) 0.028(2) Uiso 1 1 d DG . . . .
N26 N 0.6322(10) 0.5786(6) 0.0713(10) 0.0224(18) Uiso 1 1 d D . . . .
H26 H 0.5193 0.6051 0.0503 0.027 Uiso 1 1 calc R . . . .
C27 C 0.7544(11) 0.4615(7) 0.0553(13) 0.021(2) Uiso 1 1 d D . . . .
O28 O 0.7159(8) 0.3864(5) 0.0104(9) 0.0301(16) Uiso 1 1 d D . . . .
C34 C 0.9273(7) 0.5459(4) 0.1465(7) 0.021(2) Uiso 1 1 d D . . . .
C29 C 0.9347(8) 0.4436(5) 0.0990(7) 0.022(2) Uiso 1 1 d DG . . . .
C30 C 1.0967(8) 0.3398(5) 0.1006(7) 0.027(2) Uiso 1 1 d G . . . .
H30 H 1.1017 0.2713 0.0689 0.032 Uiso 1 1 calc R . . . .
C31 C 1.2513(7) 0.3382(5) 0.1497(7) 0.024(2) Uiso 1 1 d G . . . .
H31 H 1.3596 0.2687 0.1508 0.029 Uiso 1 1 calc R . . . .
C32 C 1.2439(8) 0.4405(5) 0.1972(7) 0.031(2) Uiso 1 1 d G . . . .
H32 H 1.3473 0.4395 0.2300 0.037 Uiso 1 1 calc R . . . .
C33 C 1.0819(8) 0.5444(5) 0.1956(7) 0.029(2) Uiso 1 1 d G . . . .
H33 H 1.0769 0.6128 0.2274 0.035 Uiso 1 1 calc R . . . .
S35 S 0.7167(4) 0.6648(2) 0.1332(4) 0.038(4) Uani 1 1 d D . . . .
O36 O 0.7617(8) 0.7948(5) 0.0892(9) 0.0314(16) Uiso 1 1 d D . . . .
O37 O 0.5913(11) 0.6674(6) 0.2062(12) 0.051(2) 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 C2 1.680(14) . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C4 C3 1.3900 . ?
C5 C6 1.3900 . ?
C5 C8 1.41(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C2 1.3900 . ?
C2 C3 1.3900 . ?
C3 H3 0.9300 . ?
C8 O9 1.283(19) . ?
C8 N10 1.431(16) . ?
N10 C11 1.37(2) . ?
N10 C25 1.429(10) . ?
C11 C12 1.505(19) . ?
C11 C13 1.354(11) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.50(2) . ?
C13 C18 1.417(17) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.48(2) . ?
C15 O16 1.29(2) . ?
C15 O17 1.237(9) . ?
O16 H16 0.8200 . ?
O21 C22 1.416(15) . ?
O21 C20 1.358(8) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C24 1.3900 . ?
C23 C20 1.3900 . ?
C24 H24 0.9300 . ?
C24 C25 1.3900 . ?
C25 C18 1.3900 . ?
C18 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C20 1.3900 . ?
N26 H26 0.8600 . ?
N26 C27 1.375(13) . ?
N26 S35 1.650(14) . ?
C27 O28 1.220(19) . ?
C27 C29 1.461(14) . ?
C34 C29 1.3900 . ?
C34 C33 1.3900 . ?
C34 S35 1.717(4) . ?
C29 C30 1.3900 . ?
C30 H30 0.9300 . ?
C30 C31 1.3900 . ?
C31 H31 0.9300 . ?
C31 C32 1.3900 . ?
C32 H32 0.9300 . ?
C32 C33 1.3900 . ?
C33 H33 0.9300 . ?
S35 O36 1.427(8) . ?
S35 O37 1.431(18) . ?

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
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C8 120.8(7) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C8 119.2(7) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C2 C7 C6 120.0 . . ?
C2 C7 H7 120.0 . . ?
C7 C2 Cl1 119.0(5) . . ?
C3 C2 Cl1 120.9(5) . . ?
C3 C2 C7 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C8 N10 122.2(13) . . ?
O9 C8 C5 124.6(12) . . ?
O9 C8 N10 113.3(19) . . ?
C11 N10 C8 128.7(11) . . ?
C11 N10 C25 108.1(8) . . ?
C25 N10 C8 123.2(14) . . ?
N10 C11 C12 123.9(10) . . ?
C13 C11 N10 109.5(12) . . ?
C13 C11 C12 126.6(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 126.6(14) . . ?
C11 C13 C18 108.2(13) . . ?
C18 C13 C14 125.1(7) . . ?
C13 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 C13 114.7(8) . . ?
C15 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
O16 C15 C14 114.1(9) . . ?
O17 C15 C14 123.1(17) . . ?
O17 C15 O16 122.8(16) . . ?
C15 O16 H16 109.5 . . ?
C20 O21 C22 117.2(11) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 H23 120.0 . . ?
C24 C23 C20 120.0 . . ?
C20 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 N10 133.7(7) . . ?
C18 C25 N10 106.3(7) . . ?
C18 C25 C24 120.0 . . ?
C25 C18 C13 107.9(6) . . ?
C25 C18 C19 120.0 . . ?
C19 C18 C13 132.1(6) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
O21 C20 C23 115.9(7) . . ?
O21 C20 C19 124.1(7) . . ?
C19 C20 C23 120.0 . . ?
C27 N26 H26 122.2 . . ?
C27 N26 S35 115.5(8) . . ?
S35 N26 H26 122.2 . . ?
N26 C27 C29 109.7(12) . . ?
O28 C27 N26 124.2(10) . . ?
O28 C27 C29 126.2(8) . . ?
C29 C34 C33 120.0 . . ?
C29 C34 S35 111.9(4) . . ?
C33 C34 S35 128.1(4) . . ?
C34 C29 C27 110.9(7) . . ?
C30 C29 C27 129.0(6) . . ?
C30 C29 C34 120.0 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 120.0 . . ?
C31 C32 C33 120.0 . . ?
C33 C32 H32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 H33 120.0 . . ?
N26 S35 C34 91.9(4) . . ?
O36 S35 N26 111.0(8) . . ?
O36 S35 C34 110.0(4) . . ?
O36 S35 O37 117.0(6) . . ?
O37 S35 N26 110.1(6) . . ?
O37 S35 C34 114.0(6) . . ?

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
O16 H16 O17 0.82 1.79 2.609(16) 173.2 2_477
N26 H26 O28 0.86 1.96 2.796(13) 162.7 2_665

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

data_insa_0p55GPa
_database_code_depnum_ccdc_archive 'CCDC 1902710'
loop_
_audit_author_name
_audit_author_address
'Iain Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-06-11 downloaded from the CCDC.
;
_audit_creation_date             2019-02-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid 1,2-benzisothiazol-3(2H)-one 1,1-dioxide'
_chemical_formula_moiety         'C19 H16 Cl N O4, C7 H5 N O3 S'
_chemical_formula_sum            'C26 H21 Cl N2 O7 S'
_chemical_formula_weight         540.96
_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'
S S 0.1246 0.1234 '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                   7.0133(6)
_cell_length_b                   10.155(2)
_cell_length_c                   16.607(3)
_cell_angle_alpha                79.683(14)
_cell_angle_beta                 85.829(11)
_cell_angle_gamma                79.844(14)
_cell_volume                     1144.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    599
_cell_measurement_temperature    297
_cell_measurement_theta_max      18.906
_cell_measurement_theta_min      3.157
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1025 before and 0.0509 after correction. The Ratio of minimum to maximum transmission is 0.8711. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Recrystallised from a 1:1 molar ratio of indomethacin and saccharin from ethyl acetate'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.309
_diffrn_reflns_Laue_measured_fraction_max 0.309
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3840
_diffrn_reflns_point_group_measured_fraction_full 0.309
_diffrn_reflns_point_group_measured_fraction_max 0.309
_diffrn_reflns_theta_full        23.224
_diffrn_reflns_theta_max         23.224
_diffrn_reflns_theta_min         2.953
_diffrn_ambient_temperature      297.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.309
_diffrn_measured_fraction_theta_max 0.309
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          'High pressure dataset at 0.55 GPa'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                682
_reflns_number_total             1015
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1015
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.052
_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)+(0.0626P)²+3.4878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1662
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O17-C15
 1.215 with sigma of 0.02
 C15-O16
 1.303 with sigma of 0.02
 C15-C14
 1.503 with sigma of 0.02
 C14-C13
 1.494 with sigma of 0.02
 C18-C13
 1.438 with sigma of 0.02
 C11-C13
 1.357 with sigma of 0.02
 C12-C11
 1.492 with sigma of 0.02
 C11-N10
 1.42 with sigma of 0.02
 N10-C25
 1.419 with sigma of 0.02
 N10-C8
 1.398 with sigma of 0.02
 O9-C8
 1.21 with sigma of 0.02
 C8-C5
 1.489 with sigma of 0.02
 C2-Cl1
 1.744 with sigma of 0.02
 C34-S35
 1.75 with sigma of 0.02
 S35-O37
 1.426 with sigma of 0.02
 S35-O36
 1.421 with sigma of 0.02
 N26-S35
 1.653 with sigma of 0.02
 C27-N26
 1.378 with sigma of 0.02
 C27-C29
 1.483 with sigma of 0.02
 O28-C27
 1.211 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C3(H3), C23(H23), C24(H24), C19(H19), N26(H26),
 C30(H30), C31(H31), C32(H32), C33(H33)
4.c Fitted hexagon refined as free rotating group:
 C4(C5,C6,C7,C2,C3), C23(C24,C25,C18,C19,C20), C34(C29,C30,C31,C32,C33)
4.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C22(H22a,H22b,H22c)
4.e Idealised tetrahedral OH refined as rotating group:
 O16(H16)
;
_atom_sites_solution_hydrogens   geom
_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
Cl1 Cl 0.2714(5) 0.5904(8) 0.3697(3) 0.080(6) Uani 1 1 d D U . . .
C4 C 0.1922(8) 0.8076(10) 0.5513(5) 0.023(3) Uiso 1 1 d . U . . .
H4 H 0.1698 0.8987 0.5569 0.028 Uiso 1 1 calc R . . . .
C5 C 0.2072(8) 0.7073(12) 0.6206(4) 0.026(3) Uiso 1 1 d DG U . . .
C6 C 0.2407(8) 0.5712(11) 0.6123(5) 0.046(3) Uiso 1 1 d G U . . .
H6 H 0.2507 0.5040 0.6587 0.055 Uiso 1 1 calc R . . . .
C7 C 0.2590(9) 0.5355(11) 0.5348(6) 0.056(4) Uiso 1 1 d G U . . .
H7 H 0.2814 0.4444 0.5293 0.067 Uiso 1 1 calc R . . . .
C2 C 0.2440(8) 0.6358(13) 0.4655(4) 0.029(3) Uiso 1 1 d DG U . . .
C3 C 0.2106(8) 0.7719(12) 0.4738(4) 0.028(3) Uiso 1 1 d G U . . .
H3 H 0.2005 0.8390 0.4275 0.034 Uiso 1 1 calc R . . . .
C8 C 0.1944(13) 0.7384(16) 0.7033(6) 0.027(3) Uiso 1 1 d D U . . .
O9 O 0.3151(10) 0.6762(16) 0.7533(6) 0.039(2) Uiso 1 1 d D U . . .
N10 N 0.0523(11) 0.8424(14) 0.7226(6) 0.027(2) Uiso 1 1 d D U . . .
C11 C 0.0542(12) 0.9169(16) 0.7867(7) 0.025(3) Uiso 1 1 d D U . . .
C12 C 0.2299(15) 0.898(2) 0.8360(9) 0.029(3) Uiso 1 1 d D U . . .
H12A H 0.2367 0.8145 0.8746 0.044 Uiso 1 1 calc GR . . . .
H12B H 0.2223 0.9723 0.8649 0.044 Uiso 1 1 calc GR . . . .
H12C H 0.3438 0.8934 0.8001 0.044 Uiso 1 1 calc GR . . . .
C13 C -0.1137(13) 1.0059(16) 0.7923(8) 0.023(3) Uiso 1 1 d D U . . .
C14 C -0.1727(14) 1.1014(19) 0.8505(8) 0.032(3) Uiso 1 1 d D U . . .
H14A H -0.2306 1.1886 0.8205 0.038 Uiso 1 1 calc R . . . .
H14B H -0.0584 1.1144 0.8757 0.038 Uiso 1 1 calc R . . . .
C15 C -0.3149(14) 1.0528(17) 0.9165(8) 0.034(4) Uiso 1 1 d D U . . .
O16 O -0.3626(12) 1.1357(16) 0.9685(7) 0.042(2) Uiso 1 1 d D U . . .
H16 H -0.4167 1.0977 1.0093 0.063 Uiso 1 1 calc GR . . . .
O17 O -0.3808(10) 0.9458(14) 0.9177(6) 0.040(2) Uiso 1 1 d D U . . .
O21 O -0.6786(12) 1.0718(19) 0.6099(7) 0.043(2) Uiso 1 1 d . U . . .
C22 C -0.774(2) 1.190(3) 0.6510(11) 0.044(4) Uiso 1 1 d . U . . .
H22A H -0.8958 1.2297 0.6265 0.065 Uiso 1 1 calc GR . . . .
H22B H -0.6912 1.2576 0.6440 0.065 Uiso 1 1 calc GR . . . .
H22C H -0.7969 1.1588 0.7083 0.065 Uiso 1 1 calc GR . . . .
C23 C -0.4028(10) 0.9096(10) 0.6029(4) 0.030(3) Uiso 1 1 d . U . . .
H23 H -0.4608 0.8830 0.5612 0.036 Uiso 1 1 calc R . . . .
C24 C -0.2179(9) 0.8460(10) 0.6258(5) 0.033(3) Uiso 1 1 d G U . . .
H24 H -0.1522 0.7768 0.5993 0.039 Uiso 1 1 calc R . . . .
C25 C -0.1312(7) 0.8857(10) 0.6881(5) 0.021(3) Uiso 1 1 d DG U . . .
C18 C -0.2295(9) 0.9891(10) 0.7276(4) 0.023(3) Uiso 1 1 d DG U . . .
C19 C -0.4144(9) 1.0527(10) 0.7047(4) 0.028(3) Uiso 1 1 d G U . . .
H19 H -0.4801 1.1219 0.7311 0.034 Uiso 1 1 calc R . . . .
C20 C -0.5011(7) 1.0130(10) 0.6424(4) 0.025(3) Uiso 1 1 d G U . . .
N26 N 0.6361(14) 0.5801(16) 0.0714(6) 0.035(3) Uiso 1 1 d D U . . .
H26 H 0.5252 0.6084 0.0500 0.041 Uiso 1 1 calc R . . . .
C27 C 0.7516(17) 0.4641(18) 0.0562(8) 0.041(4) Uiso 1 1 d D U . . .
O28 O 0.7153(11) 0.3918(16) 0.0120(6) 0.038(2) Uiso 1 1 d D U . . .
C34 C 0.9288(7) 0.5428(10) 0.1477(5) 0.024(3) Uiso 1 1 d D U . . .
C29 C 0.9329(7) 0.4427(10) 0.1002(4) 0.025(3) Uiso 1 1 d DG U . . .
C30 C 1.0927(9) 0.3400(10) 0.1004(4) 0.026(3) Uiso 1 1 d G U . . .
H30 H 1.0954 0.2730 0.0685 0.031 Uiso 1 1 calc R . . . .
C31 C 1.2486(6) 0.3374(10) 0.1481(5) 0.028(3) Uiso 1 1 d G U . . .
H31 H 1.3556 0.2687 0.1482 0.034 Uiso 1 1 calc R . . . .
C32 C 1.2446(7) 0.4375(10) 0.1957(4) 0.034(3) Uiso 1 1 d G U . . .
H32 H 1.3488 0.4358 0.2276 0.041 Uiso 1 1 calc R . . . .
C33 C 1.0847(9) 0.5402(10) 0.1955(5) 0.037(3) Uiso 1 1 d G U . . .
H33 H 1.0820 0.6072 0.2273 0.044 Uiso 1 1 calc R . . . .
S35 S 0.7213(4) 0.6625(6) 0.1332(2) 0.037(5) Uani 1 1 d D U . . .
O36 O 0.7657(10) 0.7879(14) 0.0898(6) 0.045(2) Uiso 1 1 d D U . . .
O37 O 0.5968(10) 0.6655(15) 0.2069(6) 0.048(2) Uiso 1 1 d D U . . .


_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 C2 1.724(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C4 C3 1.3900 . ?
C5 C6 1.3900 . ?
C5 C8 1.457(14) . ?
C6 H6 0.9300 . ?
C6 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C2 1.3900 . ?
C2 C3 1.3900 . ?
C3 H3 0.9300 . ?
C8 O9 1.237(10) . ?
C8 N10 1.384(16) . ?
N10 C11 1.414(16) . ?
N10 C25 1.413(8) . ?
C11 C12 1.493(11) . ?
C11 C13 1.360(15) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.476(18) . ?
C13 C18 1.444(12) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.503(13) . ?
C15 O16 1.299(18) . ?
C15 O17 1.250(15) . ?
O16 H16 0.8200 . ?
O21 C22 1.52(4) . ?
O21 C20 1.385(9) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C24 1.3900 . ?
C23 C20 1.3900 . ?
C24 H24 0.9300 . ?
C24 C25 1.3900 . ?
C25 C18 1.3900 . ?
C18 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C20 1.3900 . ?
N26 H26 0.8600 . ?
N26 C27 1.359(17) . ?
N26 S35 1.638(14) . ?
C27 O28 1.195(16) . ?
C27 C29 1.476(11) . ?
C34 C29 1.3900 . ?
C34 C33 1.3900 . ?
C34 S35 1.725(8) . ?
C29 C30 1.3900 . ?
C30 H30 0.9300 . ?
C30 C31 1.3900 . ?
C31 H31 0.9300 . ?
C31 C32 1.3900 . ?
C32 H32 0.9300 . ?
C32 C33 1.3900 . ?
C33 H33 0.9300 . ?
S35 O36 1.419(10) . ?
S35 O37 1.452(11) . ?

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
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C8 122.5(8) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C8 117.5(8) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C2 120.0 . . ?
C2 C7 H7 120.0 . . ?
C7 C2 Cl1 119.6(6) . . ?
C3 C2 Cl1 120.4(6) . . ?
C3 C2 C7 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
O9 C8 C5 119.7(14) . . ?
O9 C8 N10 121.5(13) . . ?
N10 C8 C5 118.7(8) . . ?
C8 N10 C11 126.5(8) . . ?
C8 N10 C25 126.9(12) . . ?
C25 N10 C11 106.3(11) . . ?
N10 C11 C12 120.5(14) . . ?
C13 C11 N10 111.5(10) . . ?
C13 C11 C12 127.9(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 129.3(10) . . ?
C11 C13 C18 105.3(13) . . ?
C18 C13 C14 125.4(11) . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C13 C14 C15 112.8(14) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
O16 C15 C14 112.5(14) . . ?
O17 C15 C14 122.1(16) . . ?
O17 C15 O16 125.4(12) . . ?
C15 O16 H16 109.5 . . ?
C20 O21 C22 111.6(14) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 H23 120.0 . . ?
C24 C23 C20 120.0 . . ?
C20 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 N10 132.4(9) . . ?
C24 C25 C18 120.0 . . ?
C18 C25 N10 107.5(9) . . ?
C25 C18 C13 109.2(9) . . ?
C19 C18 C13 130.7(8) . . ?
C19 C18 C25 120.0 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0 . . ?
C20 C19 H19 120.0 . . ?
O21 C20 C23 113.4(10) . . ?
O21 C20 C19 126.5(10) . . ?
C19 C20 C23 120.0 . . ?
C27 N26 H26 122.1 . . ?
C27 N26 S35 115.8(8) . . ?
S35 N26 H26 122.1 . . ?
N26 C27 C29 109.9(13) . . ?
O28 C27 N26 125.4(11) . . ?
O28 C27 C29 124.7(14) . . ?
C29 C34 C33 120.0 . . ?
C29 C34 S35 111.1(5) . . ?
C33 C34 S35 128.8(5) . . ?
C34 C29 C27 110.6(10) . . ?
C30 C29 C27 129.4(10) . . ?
C30 C29 C34 120.0 . . ?
C29 C30 H30 120.0 . . ?
C29 C30 C31 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 120.0 . . ?
C33 C32 H32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 H33 120.0 . . ?
N26 S35 C34 92.4(7) . . ?
O36 S35 N26 110.4(6) . . ?
O36 S35 C34 110.8(4) . . ?
O36 S35 O37 117.8(9) . . ?
O37 S35 N26 109.9(6) . . ?
O37 S35 C34 112.7(5) . . ?

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
O16 H16 O17 0.82 1.86 2.639(9) 158.2 2_477
N26 H26 O28 0.86 2.04 2.860(10) 159.4 2_665

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

data_insa_5p06GPa
_database_code_depnum_ccdc_archive 'CCDC 1902715'
loop_
_audit_author_name
_audit_author_address
'Iain Oswald'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-06-11 downloaded from the CCDC.
;
_audit_creation_date             2018-06-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid 1,2-benzisothiazol-3(2H)-one 1,1-dioxide'
_chemical_formula_moiety         'C19 H16 Cl N O4, C7 H5 N O3 S'
_chemical_formula_sum            'C26 H21 Cl N2 O7 S'
_chemical_formula_weight         540.96
_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'
S S 0.1246 0.1234 '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                   6.6623(3)
_cell_length_b                   9.3453(11)
_cell_length_c                   16.2637(15)
_cell_angle_alpha                76.764(8)
_cell_angle_beta                 84.331(6)
_cell_angle_gamma                82.375(8)
_cell_volume                     974.52(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1365
_cell_measurement_temperature    297
_cell_measurement_theta_max      22.991
_cell_measurement_theta_min      3.265
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    0.367
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0674 before and 0.0484 after correction. The Ratio of minimum to maximum transmission is 0.8882. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.844
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_recrystallization_method 
'Recrystallisation of 1:1 molar ration of indomethacin and saccharin from ethyl acetate'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.314
_diffrn_reflns_Laue_measured_fraction_max 0.314
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4517
_diffrn_reflns_point_group_measured_fraction_full 0.314
_diffrn_reflns_point_group_measured_fraction_max 0.314
_diffrn_reflns_theta_full        23.399
_diffrn_reflns_theta_max         23.399
_diffrn_reflns_theta_min         3.093
_diffrn_ambient_temperature      297.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.314
_diffrn_measured_fraction_theta_max 0.314
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          'High pressure dataset at 5.06 GPa'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                694
_reflns_number_total             894
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         894
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0671
_refine_ls_restrained_S_all      1.087
_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)+(0.0862P)²+5.7450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1714
_refine_ls_wR_factor_ref         0.1864
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C2-Cl1
 0.011 with sigma of 1.742
 C5-C8
 0.011 with sigma of 1.495
 O9-C8
 0.013 with sigma of 1.217
 C8-N10
 0.021 with sigma of 1.413
 C11-N10
 0.018 with sigma of 1.398
 C25-N10
 0.015 with sigma of 1.415
 C12-C11
 0.01 with sigma of 1.491
 C11-C13
 0.007 with sigma of 1.355
 C14-C13
 0.009 with sigma of 1.502
 C18-C13
 0.015 with sigma of 1.437
 C14-C15
 0.008 with sigma of 1.506
 O16-C15
 0.023 with sigma of 1.307
 O17-C15
 0.021 with sigma of 1.213
 C19-C18
 0.012 with sigma of 1.395
 C18-C25
 0.01 with sigma of 1.406
 O21-C20
 0.011 with sigma of 1.369
 O21-C22
 0.015 with sigma of 1.425
 C27-N26
 0.013 with sigma of 1.374
 S35-N26
 0.015 with sigma of 1.654
 O28-C27
 0.011 with sigma of 1.228
 C29-C27
 0.012 with sigma of 1.483
 C34-S35
 0.008 with sigma of 1.753
 O36-S35
 0.007 with sigma of 1.431
 O37-S35
 0.007 with sigma of 1.431
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C3(H3), C23(H23), C24(H24), C19(H19), N26(H26),
 C30(H30), C31(H31), C32(H32), C33(H33)
3.c Fitted hexagon refined as free rotating group:
 C4(C5,C6,C7,C2,C3), C23(C24,C25,C18,C19,C20), C34(C29,C30,C31,C32,C33)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C22(H22A,H22B,H22C)
3.e Idealised tetrahedral OH refined as rotating group:
 O16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.2711(5) 0.5855(7) 0.3598(3) 0.043(5) Uani 1 1 d D . . . .
C4 C 0.1773(9) 0.8071(12) 0.5437(5) 0.014(2) Uiso 1 1 d . . . . .
H4 H 0.1459 0.9048 0.5488 0.017 Uiso 1 1 calc R . . . .
C5 C 0.2077(9) 0.6949(14) 0.6154(4) 0.020(3) Uiso 1 1 d DG . . . .
C6 C 0.2546(9) 0.5489(13) 0.6077(5) 0.028(3) Uiso 1 1 d G . . . .
H6 H 0.2749 0.4738 0.6557 0.033 Uiso 1 1 calc R . . . .
C7 C 0.2712(10) 0.5152(12) 0.5282(6) 0.036(3) Uiso 1 1 d G . . . .
H7 H 0.3026 0.4175 0.5230 0.044 Uiso 1 1 calc R . . . .
C2 C 0.2408(9) 0.6274(14) 0.4564(5) 0.020(3) Uiso 1 1 d DG . . . .
C3 C 0.1938(9) 0.7733(13) 0.4642(5) 0.012(2) Uiso 1 1 d G . . . .
H3 H 0.1735 0.8484 0.4162 0.015 Uiso 1 1 calc R . . . .
C8 C 0.2044(15) 0.728(2) 0.7008(9) 0.012(2) Uiso 1 1 d D . . . .
O9 O 0.3346(10) 0.6606(17) 0.7485(7) 0.0232(19) Uiso 1 1 d D . . . .
N10 N 0.0562(14) 0.827(2) 0.7202(8) 0.017(2) Uiso 1 1 d D . . . .
C11 C 0.0599(17) 0.912(3) 0.7837(11) 0.021(3) Uiso 1 1 d D . . . .
C12 C 0.2391(16) 0.892(3) 0.8336(10) 0.017(3) Uiso 1 1 d D . . . .
H12A H 0.2128 0.8298 0.8882 0.026 Uiso 1 1 calc GR . . . .
H12B H 0.2664 0.9872 0.8404 0.026 Uiso 1 1 calc GR . . . .
H12C H 0.3546 0.8479 0.8045 0.026 Uiso 1 1 calc GR . . . .
C13 C -0.1091(18) 1.001(3) 0.7826(13) 0.022(3) Uiso 1 1 d D . . . .
C14 C -0.1611(16) 1.098(3) 0.8383(12) 0.013(3) Uiso 1 1 d D . . . .
H14A H -0.2176 1.1927 0.8054 0.016 Uiso 1 1 calc R . . . .
H14B H -0.0366 1.1147 0.8592 0.016 Uiso 1 1 calc R . . . .
C15 C -0.3091(17) 1.053(3) 0.9144(12) 0.017(3) Uiso 1 1 d D . . . .
O16 O -0.3378(15) 1.137(2) 0.9708(10) 0.042(3) Uiso 1 1 d D . . . .
H16 H -0.4327 1.1108 1.0047 0.063 Uiso 1 1 calc GR . . . .
O17 O -0.3993(11) 0.9438(16) 0.9133(6) 0.0248(19) Uiso 1 1 d D . . . .
O21 O -0.6961(13) 1.076(2) 0.6064(8) 0.027(2) Uiso 1 1 d D . . . .
C22 C -0.778(2) 1.194(3) 0.6435(13) 0.032(4) Uiso 1 1 d D . . . .
H22A H -0.8874 1.2499 0.6117 0.048 Uiso 1 1 calc GR . . . .
H22B H -0.6752 1.2561 0.6438 0.048 Uiso 1 1 calc GR . . . .
H22C H -0.8290 1.1556 0.7006 0.048 Uiso 1 1 calc GR . . . .
C23 C -0.4155(10) 0.8958(11) 0.5976(4) 0.019(3) Uiso 1 1 d . . . . .
H23 H -0.4757 0.8678 0.5554 0.023 Uiso 1 1 calc R . . . .
C24 C -0.2259(10) 0.8274(11) 0.6220(5) 0.024(3) Uiso 1 1 d G . . . .
H24 H -0.1591 0.7535 0.5962 0.028 Uiso 1 1 calc R . . . .
C25 C -0.1359(8) 0.8693(11) 0.6851(5) 0.013(2) Uiso 1 1 d DG . . . .
C18 C -0.2356(10) 0.9796(11) 0.7237(4) 0.015(2) Uiso 1 1 d DG . . . .
C19 C -0.4253(10) 1.0481(11) 0.6993(5) 0.018(3) Uiso 1 1 d DG . . . .
H19 H -0.4920 1.1219 0.7251 0.022 Uiso 1 1 calc R . . . .
C20 C -0.5152(8) 1.0062(11) 0.6362(5) 0.016(3) Uiso 1 1 d DG . . . .
N26 N 0.6221(15) 0.582(3) 0.0719(10) 0.024(2) Uiso 1 1 d D . . . .
H26 H 0.5029 0.6071 0.0536 0.028 Uiso 1 1 calc R . . . .
C27 C 0.751(2) 0.455(4) 0.0529(13) 0.020(3) Uiso 1 1 d D . . . .
O28 O 0.7123(14) 0.384(2) 0.0112(8) 0.022(2) Uiso 1 1 d D . . . .
C34 C 0.9231(7) 0.5480(11) 0.1481(5) 0.015(2) Uiso 1 1 d D . . . .
C29 C 0.9354(7) 0.4447(11) 0.0979(5) 0.015(3) Uiso 1 1 d DG . . . .
C30 C 1.1052(9) 0.3408(11) 0.0978(5) 0.019(2) Uiso 1 1 d G . . . .
H30 H 1.1134 0.2717 0.0642 0.023 Uiso 1 1 calc R . . . .
C31 C 1.2629(7) 0.3403(11) 0.1479(5) 0.018(3) Uiso 1 1 d G . . . .
H31 H 1.3765 0.2708 0.1478 0.022 Uiso 1 1 calc R . . . .
C32 C 1.2506(7) 0.4436(11) 0.1981(5) 0.014(2) Uiso 1 1 d G . . . .
H32 H 1.3561 0.4432 0.2316 0.017 Uiso 1 1 calc R . . . .
C33 C 1.0807(9) 0.5475(11) 0.1982(5) 0.020(3) Uiso 1 1 d G . . . .
H33 H 1.0726 0.6166 0.2318 0.024 Uiso 1 1 calc R . . . .
S35 S 0.7138(4) 0.6729(7) 0.1292(3) 0.028(5) Uani 1 1 d D . . . .
O36 O 0.7699(10) 0.8073(16) 0.0772(6) 0.0243(18) Uiso 1 1 d D . . . .
O37 O 0.5807(11) 0.6835(16) 0.2059(6) 0.028(2) 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 C2 1.691(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C4 C3 1.3900 . ?
C5 C6 1.3900 . ?
C5 C8 1.49(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C2 1.3900 . ?
C2 C3 1.3900 . ?
C3 H3 0.9300 . ?
C8 O9 1.231(11) . ?
C8 N10 1.32(3) . ?
N10 C11 1.44(4) . ?
N10 C25 1.424(9) . ?
C11 C12 1.478(15) . ?
C11 C13 1.31(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.41(4) . ?
C13 C18 1.40(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.52(2) . ?
C15 O16 1.32(4) . ?
C15 O17 1.26(3) . ?
O16 H16 0.8200 . ?
O21 C22 1.39(4) . ?
O21 C20 1.370(11) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C24 1.3900 . ?
C23 C20 1.3900 . ?
C24 H24 0.9300 . ?
C24 C25 1.3900 . ?
C25 C18 1.3900 . ?
C18 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C20 1.3900 . ?
N26 H26 0.8600 . ?
N26 C27 1.44(5) . ?
N26 S35 1.61(3) . ?
C27 O28 1.12(4) . ?
C27 C29 1.471(15) . ?
C34 C29 1.3900 . ?
C34 C33 1.3900 . ?
C34 S35 1.700(8) . ?
C29 C30 1.3900 . ?
C30 H30 0.9300 . ?
C30 C31 1.3900 . ?
C31 H31 0.9300 . ?
C31 C32 1.3900 . ?
C32 H32 0.9300 . ?
C32 C33 1.3900 . ?
C33 H33 0.9300 . ?
S35 O36 1.418(10) . ?
S35 O37 1.473(13) . ?

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
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C8 121.3(9) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C8 118.6(9) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C2 C7 C6 120.0 . . ?
C2 C7 H7 120.0 . . ?
C7 C2 Cl1 119.5(6) . . ?
C3 C2 Cl1 120.5(6) . . ?
C3 C2 C7 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
O9 C8 C5 118.3(19) . . ?
O9 C8 N10 125.1(19) . . ?
N10 C8 C5 116.6(9) . . ?
C8 N10 C11 125.4(11) . . ?
C8 N10 C25 128.2(18) . . ?
C25 N10 C11 106.4(17) . . ?
N10 C11 C12 120(2) . . ?
C13 C11 N10 108.0(16) . . ?
C13 C11 C12 132(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 123.9(17) . . ?
C11 C13 C18 111(3) . . ?
C18 C13 C14 125.0(16) . . ?
C13 C14 H14A 107.7 . . ?
C13 C14 H14B 107.7 . . ?
C13 C14 C15 118(2) . . ?
H14A C14 H14B 107.1 . . ?
C15 C14 H14A 107.7 . . ?
C15 C14 H14B 107.7 . . ?
O16 C15 C14 118(2) . . ?
O17 C15 C14 115(3) . . ?
O17 C15 O16 127.3(14) . . ?
C15 O16 H16 109.5 . . ?
C20 O21 C22 114.3(15) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 H23 120.0 . . ?
C24 C23 C20 120.0 . . ?
C20 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 N10 133.1(11) . . ?
C18 C25 N10 106.8(11) . . ?
C18 C25 C24 120.0 . . ?
C25 C18 C13 107.8(14) . . ?
C25 C18 C19 120.0 . . ?
C19 C18 C13 132.2(14) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
O21 C20 C23 117.7(11) . . ?
O21 C20 C19 122.2(11) . . ?
C19 C20 C23 120.0 . . ?
C27 N26 H26 122.0 . . ?
C27 N26 S35 116.1(11) . . ?
S35 N26 H26 122.0 . . ?
N26 C27 C29 106(3) . . ?
O28 C27 N26 124.6(12) . . ?
O28 C27 C29 130(3) . . ?
C29 C34 C33 120.0 . . ?
C29 C34 S35 110.8(6) . . ?
C33 C34 S35 128.9(5) . . ?
C34 C29 C27 112.9(17) . . ?
C34 C29 C30 120.0 . . ?
C30 C29 C27 127.0(17) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 120.0 . . ?
C31 C32 C33 120.0 . . ?
C33 C32 H32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 H33 120.0 . . ?
N26 S35 C34 93.5(9) . . ?
O36 S35 N26 109.0(7) . . ?
O36 S35 C34 109.9(5) . . ?
O36 S35 O37 116.9(10) . . ?
O37 S35 N26 111.6(7) . . ?
O37 S35 C34 113.4(4) . . ?

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
C12 H12C O9 0.96 2.17 2.80(3) 121.8 .
O16 H16 O17 0.82 1.68 2.496(12) 170.4 2_477
N26 H26 O28 0.86 1.84 2.665(12) 159.0 2_665

_olex2_submission_special_instructions 'No special instructions were received'
