# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_jk_2
_database_code_depnum_ccdc_archive 'CCDC 1533651'
_audit_update_record             
;
2017-02-20 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;
_audit_creation_date             2017-02-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
4-((fluoromethyl)sulfonyl)-1-phenylbutan-2-one
;
_chemical_formula_moiety         'C11 H13 F O3 S'
_chemical_formula_sum            'C11 H13 F O3 S'
_chemical_formula_weight         244.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H13 O3 S1 F1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.2903(14)
_cell_length_b                   5.0921(4)
_cell_length_c                   16.0912(14)
_cell_angle_alpha                90
_cell_angle_beta                 115.067(11)
_cell_angle_gamma                90
_cell_volume                     1134.85(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2882
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      67.0260
_cell_measurement_theta_min      3.1620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0878
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9604
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.402
_diffrn_reflns_theta_max         67.402
_diffrn_reflns_theta_min         3.191
_diffrn_ambient_temperature      123.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -179.00   0.00   1.00   20.00    --  -90.00  60.00-108.00  179
  2  ω   -110.00  69.00   1.00   10.00    --  -21.00  30.00 -36.00  179
  3  ω   -179.00   0.00   1.00   20.00    --  -90.00  60.00-180.00  179
  4  ω   -179.00   0.00   1.00   20.00    --  -90.00  60.00 -36.00  179
  5  ω   -179.00   0.00   1.00   20.00    --  -90.00  30.00-108.00  179
  6  ω   -179.00   0.00   1.00   20.00    --  -90.00  30.00-180.00  179
  7  ω   -179.00   0.00   1.00   20.00    --  -90.00  30.00 -36.00  179
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn944+ (2x2 bin mode)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0077305000
_diffrn_orient_matrix_UB_12      -0.2961120000
_diffrn_orient_matrix_UB_13      -0.0217664000
_diffrn_orient_matrix_UB_21      0.1027948000
_diffrn_orient_matrix_UB_22      -0.0415683000
_diffrn_orient_matrix_UB_23      0.0755020000
_diffrn_orient_matrix_UB_31      -0.0417140000
_diffrn_orient_matrix_UB_32      -0.0466730000
_diffrn_orient_matrix_UB_33      0.0706842000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-003'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1631
_reflns_number_total             2005
_reflns_odcompleteness_completeness 98.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.29
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       
;
Rigaku Collection Strategy
(Daniels, L. M. (2011). Acta Cryst. A67, C143)
;
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    
;
Mercury CSD 3.9 (Macrae, C. F., et al. (2006). J. Appl. Cryst. 39, 453-457)
POV-Ray 3.7 (Persistence of Vision Pty. Ltd. (2004)) 
;
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2005
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0562
_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)+(0.0738P)²+0.7657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1565
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
;
_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
C1 C 0.7437(2) 0.2848(7) 0.6983(2) 0.0367(8) Uani 1 1 d . . . . .
H1A H 0.800344 0.167561 0.715347 0.044 Uiso 1 1 calc R . . . .
H1B H 0.734018 0.376421 0.640814 0.044 Uiso 1 1 calc R . . . .
C2 C 0.5404(2) 0.3079(6) 0.6240(2) 0.0305(7) Uani 1 1 d . . . . .
H2A H 0.548517 0.467698 0.661559 0.037 Uiso 1 1 calc R . . . .
H2B H 0.538060 0.361488 0.563908 0.037 Uiso 1 1 calc R . . . .
C3 C 0.4478(2) 0.1701(6) 0.6100(2) 0.0298(7) Uani 1 1 d . . . . .
H3A H 0.447920 0.134500 0.670561 0.036 Uiso 1 1 calc R . . . .
H3B H 0.444511 -0.000576 0.579398 0.036 Uiso 1 1 calc R . . . .
C4 C 0.3599(2) 0.3315(6) 0.5528(2) 0.0271(7) Uani 1 1 d . . . . .
C5 C 0.2645(2) 0.1999(6) 0.5330(2) 0.0315(7) Uani 1 1 d . . . . .
H5A H 0.259339 0.039169 0.496573 0.038 Uiso 1 1 calc R . . . .
H5B H 0.264145 0.145060 0.591870 0.038 Uiso 1 1 calc R . . . .
C6 C 0.1770(2) 0.3690(6) 0.4819(2) 0.0297(7) Uani 1 1 d . . . . .
C7 C 0.1553(2) 0.5719(7) 0.5274(2) 0.0392(8) Uani 1 1 d . . . . .
H7 H 0.195944 0.603215 0.590258 0.047 Uiso 1 1 calc R . . . .
C8 C 0.0753(3) 0.7298(7) 0.4824(3) 0.0483(9) Uani 1 1 d . . . . .
H8 H 0.061125 0.867543 0.514629 0.058 Uiso 1 1 calc R . . . .
C9 C 0.0158(2) 0.6874(7) 0.3907(2) 0.0428(8) Uani 1 1 d . . . . .
H9 H -0.039289 0.794834 0.359667 0.051 Uiso 1 1 calc R . . . .
C10 C 0.0375(2) 0.4881(7) 0.3451(2) 0.0419(8) Uani 1 1 d . . . . .
H10 H -0.002396 0.459057 0.281946 0.050 Uiso 1 1 calc R . . . .
C11 C 0.1174(2) 0.3286(7) 0.3906(2) 0.0396(8) Uani 1 1 d . . . . .
H11 H 0.131098 0.190068 0.358409 0.047 Uiso 1 1 calc R . . . .
F1 F 0.76131(14) 0.4664(4) 0.76677(13) 0.0457(5) Uani 1 1 d . . . . .
O1 O 0.64151(16) 0.0163(5) 0.76685(15) 0.0411(6) Uani 1 1 d . . . . .
O2 O 0.63786(17) -0.1089(4) 0.61701(16) 0.0380(6) Uani 1 1 d . . . . .
O3 O 0.36631(14) 0.5513(4) 0.52522(14) 0.0316(5) Uani 1 1 d . . . . .
S1 S 0.63892(5) 0.09295(14) 0.67992(5) 0.0310(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 F1 1.374(4) . ?
C1 S1 1.791(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.509(4) . ?
C2 S1 1.768(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.511(4) . ?
C4 C5 1.511(4) . ?
C4 O3 1.223(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.509(4) . ?
C6 C7 1.385(5) . ?
C6 C11 1.376(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.372(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(5) . ?
C11 H11 0.9500 . ?
O1 S1 1.437(2) . ?
O2 S1 1.438(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 108.0 . . ?
F1 C1 H1A 109.5 . . ?
F1 C1 H1B 109.5 . . ?
F1 C1 S1 110.9(2) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C3 C2 S1 109.3(2) . . ?
S1 C2 H2A 109.8 . . ?
S1 C2 H2B 109.8 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C2 C3 C4 112.0(2) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C3 C4 C5 114.7(3) . . ?
O3 C4 C3 122.1(3) . . ?
O3 C4 C5 123.2(3) . . ?
C4 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 C4 114.6(3) . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
C7 C6 C5 119.5(3) . . ?
C11 C6 C5 122.0(3) . . ?
C11 C6 C7 118.5(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.2(3) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.5(3) . . ?
C11 C10 H10 119.7 . . ?
C6 C11 C10 120.8(3) . . ?
C6 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C2 S1 C1 104.82(15) . . ?
O1 S1 C1 109.47(15) . . ?
O1 S1 C2 109.27(15) . . ?
O1 S1 O2 118.61(14) . . ?
O2 S1 C1 104.42(15) . . ?
O2 S1 C2 109.32(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.036
_oxdiff_exptl_absorpt_empirical_full_min 0.448
