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

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

data_3ca
_database_code_depnum_ccdc_archive 'CCDC 2071406'
loop_
_audit_author_name
_audit_author_address
'Dineshchakravarthy Senthurpandi'
;Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore, Karnataka
India
;
_audit_update_record             
;
2021-03-18 deposited with the CCDC.	2021-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        
3-isopropyl-1-phenyl-2-(trifluoromethylsulfonyl)-1,2-dihydropyrazol-5-one
_chemical_name_common            ?
_chemical_melting_point          401
_chemical_formula_moiety         'C13 H13 F3 N2 O3 S'
_chemical_formula_sum            'C13 H13 F3 N2 O3 S'
_chemical_formula_weight         334.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   8.6070(5)
_cell_length_b                   14.6316(8)
_cell_length_c                   22.5134(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2835.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9222
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      28.35

_exptl_crystal_description       TABULAR
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             1376
_exptl_crystal_recrystallization_method 'slow evaporation from ethyl acetate'
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.092
_exptl_absorpt_coefficient_mu    0.277
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5914
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS-2016/2
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60045
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.809
_diffrn_reflns_theta_max         28.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3541
_reflns_number_gt                3310
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+2.4123P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3541
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0938
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.63482(14) 0.34975(8) 0.40253(5) 0.0146(2) Uani 1 1 d . . . . .
N2 N 0.73997(14) 0.40207(8) 0.36765(5) 0.0143(2) Uani 1 1 d . . . . .
C3 C 0.88479(16) 0.40606(9) 0.39978(6) 0.0142(3) Uani 1 1 d . . . . .
C4 C 0.87024(16) 0.35751(10) 0.44983(6) 0.0157(3) Uani 1 1 d . . . . .
H4 H 0.949687 0.349605 0.478669 0.019 Uiso 1 1 calc R U . . .
C5 C 0.71498(17) 0.31860(10) 0.45365(6) 0.0150(3) Uani 1 1 d . . . . .
C11 C 0.53134(16) 0.28927(9) 0.37146(6) 0.0140(3) Uani 1 1 d . . . . .
C12 C 0.56143(17) 0.26073(10) 0.31375(6) 0.0180(3) Uani 1 1 d . . . . .
H12 H 0.650374 0.282286 0.293057 0.022 Uiso 1 1 calc R U . . .
C13 C 0.45911(18) 0.20009(11) 0.28683(7) 0.0206(3) Uani 1 1 d . . . . .
H13 H 0.477469 0.180850 0.247145 0.025 Uiso 1 1 calc R U . . .
C14 C 0.33060(18) 0.16735(10) 0.31718(7) 0.0202(3) Uani 1 1 d . . . . .
H14 H 0.261795 0.125468 0.298533 0.024 Uiso 1 1 calc R U . . .
C15 C 0.30302(17) 0.19602(10) 0.37487(7) 0.0186(3) Uani 1 1 d . . . . .
H15 H 0.215563 0.173189 0.395905 0.022 Uiso 1 1 calc R U . . .
C16 C 0.40245(16) 0.25796(10) 0.40215(6) 0.0154(3) Uani 1 1 d . . . . .
H16 H 0.382237 0.278584 0.441413 0.019 Uiso 1 1 calc R U . . .
S21 S 0.65986(4) 0.49911(2) 0.34236(2) 0.01531(10) Uani 1 1 d . . . . .
F21 F 0.59417(12) 0.65647(7) 0.38816(5) 0.0321(2) Uani 1 1 d . . . . .
O21 O 0.76715(13) 0.53873(8) 0.30217(5) 0.0210(2) Uani 1 1 d . . . . .
C21 C 0.65100(19) 0.57726(11) 0.40678(7) 0.0215(3) Uani 1 1 d . . . . .
F22 F 0.79129(12) 0.59138(7) 0.42886(5) 0.0308(2) Uani 1 1 d . . . . .
O22 O 0.50336(13) 0.48080(8) 0.32697(5) 0.0207(2) Uani 1 1 d . . . . .
F23 F 0.56047(15) 0.54421(8) 0.44852(5) 0.0392(3) Uani 1 1 d . . . . .
C31 C 1.02445(16) 0.45259(10) 0.37432(6) 0.0166(3) Uani 1 1 d . . . . .
H31 H 0.994560 0.516079 0.362490 0.020 Uiso 1 1 calc R U . . .
C32 C 1.15305(17) 0.45834(11) 0.42091(7) 0.0205(3) Uani 1 1 d . . . . .
H32A H 1.117062 0.494993 0.454650 0.031 Uiso 1 1 calc R U . . .
H32B H 1.245159 0.487034 0.403388 0.031 Uiso 1 1 calc R U . . .
H32C H 1.179458 0.396687 0.434601 0.031 Uiso 1 1 calc R U . . .
C33 C 1.07890(19) 0.40092(12) 0.31866(7) 0.0242(3) Uani 1 1 d . . . . .
H33A H 1.104227 0.337699 0.329275 0.036 Uiso 1 1 calc R U . . .
H33B H 1.171336 0.430897 0.302330 0.036 Uiso 1 1 calc R U . . .
H33C H 0.995869 0.401227 0.288874 0.036 Uiso 1 1 calc R U . . .
O51 O 0.65842(13) 0.26692(7) 0.48984(5) 0.0198(2) 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
N1 C5 1.4172(17) . ?
N1 N2 1.4218(16) . ?
N1 C11 1.4372(17) . ?
N2 C3 1.4423(17) . ?
N2 S21 1.6780(12) . ?
C3 C4 1.338(2) . ?
C3 C31 1.4957(19) . ?
C4 C5 1.4551(19) . ?
C4 H4 0.9500 . ?
C5 O51 1.2134(17) . ?
C11 C16 1.3850(19) . ?
C11 C12 1.389(2) . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
S21 O22 1.4164(11) . ?
S21 O21 1.4168(11) . ?
S21 C21 1.8485(16) . ?
F21 C21 1.3259(18) . ?
C21 F23 1.3130(19) . ?
C21 F22 1.3220(18) . ?
C31 C32 1.527(2) . ?
C31 C33 1.537(2) . ?
C31 H31 1.0000 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 N2 108.17(11) . . ?
C5 N1 C11 119.93(11) . . ?
N2 N1 C11 117.21(11) . . ?
N1 N2 C3 107.15(10) . . ?
N1 N2 S21 112.43(9) . . ?
C3 N2 S21 119.41(10) . . ?
C4 C3 N2 108.66(12) . . ?
C4 C3 C31 129.77(13) . . ?
N2 C3 C31 121.39(12) . . ?
C3 C4 C5 110.09(12) . . ?
C3 C4 H4 125.0 . . ?
C5 C4 H4 125.0 . . ?
O51 C5 N1 123.39(13) . . ?
O51 C5 C4 130.69(13) . . ?
N1 C5 C4 105.86(12) . . ?
C16 C11 C12 121.10(13) . . ?
C16 C11 N1 117.21(12) . . ?
C12 C11 N1 121.65(13) . . ?
C11 C12 C13 118.80(14) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 120.78(14) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 119.63(14) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.42(14) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 119.24(13) . . ?
C11 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
O22 S21 O21 122.75(7) . . ?
O22 S21 N2 108.29(6) . . ?
O21 S21 N2 107.16(6) . . ?
O22 S21 C21 105.65(7) . . ?
O21 S21 C21 105.95(7) . . ?
N2 S21 C21 105.91(7) . . ?
F23 C21 F22 109.30(14) . . ?
F23 C21 F21 109.22(13) . . ?
F22 C21 F21 108.61(13) . . ?
F23 C21 S21 110.99(11) . . ?
F22 C21 S21 110.74(11) . . ?
F21 C21 S21 107.93(11) . . ?
C3 C31 C32 110.14(12) . . ?
C3 C31 C33 109.49(12) . . ?
C32 C31 C33 111.48(12) . . ?
C3 C31 H31 108.6 . . ?
C32 C31 H31 108.6 . . ?
C33 C31 H31 108.6 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 C3 -2.62(14) . . . . ?
C11 N1 N2 C3 -142.00(12) . . . . ?
C5 N1 N2 S21 -135.73(10) . . . . ?
C11 N1 N2 S21 84.89(13) . . . . ?
N1 N2 C3 C4 1.59(15) . . . . ?
S21 N2 C3 C4 130.82(11) . . . . ?
N1 N2 C3 C31 177.13(12) . . . . ?
S21 N2 C3 C31 -53.65(16) . . . . ?
N2 C3 C4 C5 0.04(16) . . . . ?
C31 C3 C4 C5 -175.01(14) . . . . ?
N2 N1 C5 O51 -174.80(13) . . . . ?
C11 N1 C5 O51 -36.7(2) . . . . ?
N2 N1 C5 C4 2.60(15) . . . . ?
C11 N1 C5 C4 140.69(13) . . . . ?
C3 C4 C5 O51 175.48(15) . . . . ?
C3 C4 C5 N1 -1.65(16) . . . . ?
C5 N1 C11 C16 63.01(17) . . . . ?
N2 N1 C11 C16 -162.52(12) . . . . ?
C5 N1 C11 C12 -114.88(15) . . . . ?
N2 N1 C11 C12 19.59(19) . . . . ?
C16 C11 C12 C13 0.3(2) . . . . ?
N1 C11 C12 C13 178.12(13) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C12 C11 C16 C15 0.9(2) . . . . ?
N1 C11 C16 C15 -177.03(13) . . . . ?
C14 C15 C16 C11 -1.3(2) . . . . ?
N1 N2 S21 O22 -37.99(11) . . . . ?
C3 N2 S21 O22 -164.78(10) . . . . ?
N1 N2 S21 O21 -172.29(9) . . . . ?
C3 N2 S21 O21 60.92(12) . . . . ?
N1 N2 S21 C21 74.94(10) . . . . ?
C3 N2 S21 C21 -51.85(12) . . . . ?
O22 S21 C21 F23 51.83(13) . . . . ?
O21 S21 C21 F23 -176.53(11) . . . . ?
N2 S21 C21 F23 -62.92(13) . . . . ?
O22 S21 C21 F22 173.42(11) . . . . ?
O21 S21 C21 F22 -54.95(13) . . . . ?
N2 S21 C21 F22 58.67(12) . . . . ?
O22 S21 C21 F21 -67.82(12) . . . . ?
O21 S21 C21 F21 63.82(12) . . . . ?
N2 S21 C21 F21 177.43(10) . . . . ?
C4 C3 C31 C32 -13.5(2) . . . . ?
N2 C3 C31 C32 171.99(12) . . . . ?
C4 C3 C31 C33 109.41(17) . . . . ?
N2 C3 C31 C33 -65.09(17) . . . . ?

_refine_diff_density_max         0.524
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.056

