# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_a51117a
_audit_block_doi                 10.5517/ccdc.csd.cc1lvyhw
_database_code_depnum_ccdc_archive 'CCDC 1485659'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H17 F3 N2 O3 S'
_chemical_formula_weight         350.35

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.849(5)
_cell_length_b                   10.773(6)
_cell_length_c                   17.758(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.599(7)
_cell_angle_gamma                90
_cell_volume                     1692.3(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    974
_cell_measurement_theta_min      2.601
_cell_measurement_theta_max      25.369

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.235
_shelx_estimated_absorpt_T_min   0.895
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.297
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7549
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.211
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3295
_reflns_number_gt                2000
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1134P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3295
_refine_ls_number_parameters     213
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.1857
_refine_ls_wR_factor_gt          0.1757
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.964
_refine_ls_shift/su_max          0.007
_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
S1 S -0.10462(7) 0.15621(7) 0.22981(4) 0.0653(3) Uani 1 1 d . . . . .
N1 N 0.0597(2) -0.0345(2) 0.25928(12) 0.0613(6) Uani 1 1 d . . . . .
N2 N 0.0531(3) 0.0811(2) 0.22211(14) 0.0702(7) Uani 1 1 d D . . . .
O1 O 0.1871(2) -0.2685(2) 0.29190(14) 0.0909(7) Uani 1 1 d . . . . .
O2 O -0.0794(2) 0.2762(2) 0.19954(11) 0.0836(6) Uani 1 1 d . . . . .
O3 O -0.2220(2) 0.0810(2) 0.19840(11) 0.0860(7) Uani 1 1 d . . . . .
F1 F -0.3072(4) 0.2019(3) 0.46251(14) 0.1515(11) Uani 1 1 d . . . . .
F2 F -0.4516(3) 0.0624(4) 0.42806(14) 0.1752(14) Uani 1 1 d . . . . .
F3 F -0.2411(4) 0.0223(3) 0.47576(14) 0.1674(12) Uani 1 1 d . . . . .
C1 C 0.1980(4) -0.1695(3) 0.3436(2) 0.0892(10) Uani 1 1 d . . . . .
H1A H 0.2899 -0.1786 0.3742 0.107 Uiso 1 1 calc R U . . .
H1B H 0.1130 -0.1727 0.3768 0.107 Uiso 1 1 calc R U . . .
C2 C 0.1996(3) -0.0461(3) 0.30457(17) 0.0733(8) Uani 1 1 d . . . . .
H2A H 0.2064 0.0203 0.3414 0.088 Uiso 1 1 calc R U . . .
H2B H 0.2863 -0.0406 0.2725 0.088 Uiso 1 1 calc R U . . .
C3 C 0.0530(3) -0.1351(3) 0.20382(18) 0.0802(9) Uani 1 1 d . . . . .
H3A H 0.1396 -0.1306 0.1716 0.096 Uiso 1 1 calc R U . . .
H3B H -0.0381 -0.1277 0.1725 0.096 Uiso 1 1 calc R U . . .
C4 C 0.0532(4) -0.2553(3) 0.2448(3) 0.1035(12) Uani 1 1 d . . . . .
H4A H -0.0353 -0.2599 0.2757 0.124 Uiso 1 1 calc R U . . .
H4B H 0.0480 -0.3229 0.2088 0.124 Uiso 1 1 calc R U . . .
C5 C -0.1388(3) 0.1683(3) 0.32899(15) 0.0605(7) Uani 1 1 d . . . . .
C6 C -0.2485(3) 0.0982(3) 0.35308(16) 0.0727(8) Uani 1 1 d . . . . .
H6 H -0.2936 0.0446 0.3181 0.087 Uiso 1 1 calc R U . . .
C7 C -0.3071(5) 0.0953(4) 0.4291(2) 0.0963(10) Uani 1 1 d . . . . .
C8 C -0.0362(3) 0.2519(3) 0.37263(14) 0.0600(7) Uani 1 1 d . . . . .
C9 C 0.0554(3) 0.2047(3) 0.42925(16) 0.0801(9) Uani 1 1 d . . . . .
H9 H 0.0511 0.1204 0.4403 0.096 Uiso 1 1 calc R U . . .
C10 C 0.1536(4) 0.2798(4) 0.4700(2) 0.0962(11) Uani 1 1 d . . . . .
H10 H 0.2134 0.2454 0.5085 0.115 Uiso 1 1 calc R U . . .
C11 C 0.1648(4) 0.4034(4) 0.4551(2) 0.0909(10) Uani 1 1 d . . . . .
C12 C 0.0719(4) 0.4505(3) 0.3992(2) 0.0913(10) Uani 1 1 d . . . . .
H12 H 0.0758 0.5350 0.3887 0.110 Uiso 1 1 calc R U . . .
C13 C -0.0279(3) 0.3764(3) 0.35773(18) 0.0758(8) Uani 1 1 d . . . . .
H13 H -0.0890 0.4112 0.3199 0.091 Uiso 1 1 calc R U . . .
C14 C 0.2772(5) 0.4871(5) 0.4965(2) 0.1395(18) Uani 1 1 d . . . . .
H14A H 0.2844 0.4634 0.5486 0.209 Uiso 1 1 calc R U . . .
H14B H 0.2438 0.5717 0.4927 0.209 Uiso 1 1 calc R U . . .
H14C H 0.3746 0.4792 0.4745 0.209 Uiso 1 1 calc R U . . .
H2 H 0.118(3) 0.130(2) 0.2221(14) 0.060(8) 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
S1 O3 1.419(2) . ?
S1 O2 1.420(2) . ?
S1 N2 1.622(3) . ?
S1 C5 1.800(3) . ?
N1 N2 1.410(3) . ?
N1 C2 1.462(3) . ?
N1 C3 1.465(4) . ?
N2 H2 0.78(2) . ?
O1 C1 1.409(4) . ?
O1 C4 1.437(4) . ?
F1 C7 1.292(5) . ?
F2 C7 1.326(4) . ?
F3 C7 1.272(4) . ?
C1 C2 1.499(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.486(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.312(4) . ?
C5 C8 1.482(4) . ?
C6 C7 1.461(4) . ?
C6 H6 0.9300 . ?
C8 C13 1.370(4) . ?
C8 C9 1.371(4) . ?
C9 C10 1.378(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.362(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.368(5) . ?
C11 C14 1.518(5) . ?
C12 C13 1.387(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 119.47(13) . . ?
O3 S1 N2 107.73(15) . . ?
O2 S1 N2 106.09(13) . . ?
O3 S1 C5 106.55(13) . . ?
O2 S1 C5 109.67(14) . . ?
N2 S1 C5 106.68(12) . . ?
N2 N1 C2 110.9(2) . . ?
N2 N1 C3 109.8(2) . . ?
C2 N1 C3 108.9(2) . . ?
N1 N2 S1 115.19(18) . . ?
N1 N2 H2 125(2) . . ?
S1 N2 H2 108(2) . . ?
C1 O1 C4 110.1(2) . . ?
O1 C1 C2 111.8(3) . . ?
O1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
N1 C2 C1 108.2(3) . . ?
N1 C2 H2A 110.1 . . ?
C1 C2 H2A 110.1 . . ?
N1 C2 H2B 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
N1 C3 C4 108.4(3) . . ?
N1 C3 H3A 110.0 . . ?
C4 C3 H3A 110.0 . . ?
N1 C3 H3B 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
O1 C4 C3 111.2(3) . . ?
O1 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
O1 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C8 128.9(3) . . ?
C6 C5 S1 115.0(2) . . ?
C8 C5 S1 116.02(19) . . ?
C5 C6 C7 126.8(3) . . ?
C5 C6 H6 116.6 . . ?
C7 C6 H6 116.6 . . ?
F3 C7 F1 104.9(3) . . ?
F3 C7 F2 105.6(3) . . ?
F1 C7 F2 103.3(4) . . ?
F3 C7 C6 116.5(3) . . ?
F1 C7 C6 114.2(3) . . ?
F2 C7 C6 111.1(3) . . ?
C13 C8 C9 118.1(3) . . ?
C13 C8 C5 122.0(2) . . ?
C9 C8 C5 120.0(3) . . ?
C8 C9 C10 121.3(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 117.3(3) . . ?
C10 C11 C14 122.5(4) . . ?
C12 C11 C14 120.2(4) . . ?
C11 C12 C13 122.2(3) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C8 C13 C12 119.9(3) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
N2 H2 O1 0.78(2) 2.06(2) 2.829(3) 168(3) 2

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.101

_shelxl_version_number           2013-2



