# Electronic Supplementary Material (ESI) for ChemComm.
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 1530094'
_audit_update_record             
;
2017-01-30 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
6-Trifluormethansulfonat-2-phenyl-1,3-benzoxazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 F3 N O4 S'
_chemical_formula_sum            'C14 H8 F3 N O4 S'
_chemical_formula_weight         343.27

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   16.5356(13)
_cell_length_b                   7.3275(4)
_cell_length_c                   11.8114(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.518(6)
_cell_angle_gamma                90
_cell_volume                     1364.75(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    11848
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.19

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.294
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 132 frames, detector distance = 70 mm
;
_diffrn_reflns_number            6953
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.583
_diffrn_reflns_theta_max         28.164
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3288
_reflns_number_gt                2619
_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    SIR-2004
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0374P)²+0.7832P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3288
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_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
C1 C 0.53996(9) 0.1896(2) 0.64170(13) 0.0177(3) Uani 1 1 d . . . . .
N2 N 0.51990(8) 0.27445(18) 0.54070(11) 0.0197(3) Uani 1 1 d . . . . .
C3 C 0.43382(10) 0.2344(2) 0.48881(13) 0.0185(3) Uani 1 1 d . . . . .
C4 C 0.37720(10) 0.2843(2) 0.37988(14) 0.0212(3) Uani 1 1 d . . . . .
H4 H 0.394404 0.359989 0.325999 0.025 Uiso 1 1 calc R U . . .
C5 C 0.29461(10) 0.2194(2) 0.35296(13) 0.0215(3) Uani 1 1 d . . . . .
H5 H 0.254046 0.250352 0.279596 0.026 Uiso 1 1 calc R U . . .
C6 C 0.27163(9) 0.1089(2) 0.43377(13) 0.0196(3) Uani 1 1 d . . . . .
C7 C 0.32570(10) 0.0549(2) 0.54244(14) 0.0201(3) Uani 1 1 d . . . . .
H7 H 0.308575 -0.021878 0.595841 0.024 Uiso 1 1 calc R U . . .
C8 C 0.40693(10) 0.1232(2) 0.56601(13) 0.0186(3) Uani 1 1 d . . . . .
O9 O 0.47471(7) 0.09385(15) 0.66518(9) 0.0191(2) Uani 1 1 d . . . . .
C10 C 0.62329(9) 0.1790(2) 0.73011(13) 0.0179(3) Uani 1 1 d . . . . .
C11 C 0.69253(10) 0.2591(2) 0.70441(14) 0.0204(3) Uani 1 1 d . . . . .
H11 H 0.684300 0.324043 0.632203 0.024 Uiso 1 1 calc R U . . .
C12 C 0.77299(10) 0.2438(2) 0.78405(14) 0.0230(3) Uani 1 1 d . . . . .
H12 H 0.819754 0.300623 0.767311 0.028 Uiso 1 1 calc R U . . .
C13 C 0.78547(10) 0.1454(2) 0.88856(14) 0.0234(3) Uani 1 1 d . . . . .
H13 H 0.840944 0.132052 0.942182 0.028 Uiso 1 1 calc R U . . .
C14 C 0.71661(10) 0.0667(2) 0.91442(14) 0.0225(3) Uani 1 1 d . . . . .
H14 H 0.725281 0.000191 0.986126 0.027 Uiso 1 1 calc R U . . .
C15 C 0.63537(10) 0.0844(2) 0.83657(13) 0.0205(3) Uani 1 1 d . . . . .
H15 H 0.588372 0.032570 0.855480 0.025 Uiso 1 1 calc R U . . .
O16 O 0.18830(7) 0.03331(16) 0.39625(10) 0.0233(2) Uani 1 1 d . . . . .
S17 S 0.11872(2) 0.08585(6) 0.45639(4) 0.02283(10) Uani 1 1 d . . . . .
O18 O 0.15462(8) 0.17201(19) 0.56730(11) 0.0322(3) Uani 1 1 d . . . . .
O19 O 0.06385(8) -0.06567(17) 0.44060(12) 0.0322(3) Uani 1 1 d . . . . .
C20 C 0.06184(12) 0.2608(3) 0.35191(19) 0.0374(4) Uani 1 1 d . . . . .
F21 F 0.11326(7) 0.39706(15) 0.34765(11) 0.0417(3) Uani 1 1 d . . . . .
F22 F 0.03207(10) 0.1896(2) 0.24511(12) 0.0697(5) Uani 1 1 d . . . . .
F23 F -0.00094(9) 0.3240(2) 0.38674(17) 0.0722(5) 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 N2 1.2967(19) . ?
C1 O9 1.3832(17) . ?
C1 C10 1.459(2) . ?
N2 C3 1.401(2) . ?
C3 C8 1.392(2) . ?
C3 C4 1.393(2) . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(2) . ?
C6 O16 1.4264(18) . ?
C7 C8 1.381(2) . ?
C7 H7 0.9500 . ?
C8 O9 1.3727(18) . ?
C10 C15 1.397(2) . ?
C10 C11 1.399(2) . ?
C11 C12 1.383(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
O16 S17 1.5711(11) . ?
S17 O19 1.4103(13) . ?
S17 O18 1.4139(13) . ?
S17 C20 1.831(2) . ?
C20 F23 1.311(2) . ?
C20 F22 1.316(3) . ?
C20 F21 1.322(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
N2 C1 O9 115.39(13) . . ?
N2 C1 C10 127.51(13) . . ?
O9 C1 C10 117.06(12) . . ?
C1 N2 C3 104.28(12) . . ?
C8 C3 C4 120.02(14) . . ?
C8 C3 N2 108.61(13) . . ?
C4 C3 N2 131.37(14) . . ?
C5 C4 C3 117.54(14) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
C6 C5 C4 119.71(14) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 C6 C5 124.78(14) . . ?
C7 C6 O16 118.12(13) . . ?
C5 C6 O16 116.84(14) . . ?
C8 C7 C6 113.67(14) . . ?
C8 C7 H7 123.2 . . ?
C6 C7 H7 123.2 . . ?
O9 C8 C7 127.61(13) . . ?
O9 C8 C3 108.11(13) . . ?
C7 C8 C3 124.28(15) . . ?
C8 O9 C1 103.61(11) . . ?
C15 C10 C11 119.94(14) . . ?
C15 C10 C1 121.28(13) . . ?
C11 C10 C1 118.72(13) . . ?
C12 C11 C10 120.05(14) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.08(14) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.86(15) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 120.64(14) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 119.39(14) . . ?
C14 C15 H15 120.3 . . ?
C10 C15 H15 120.3 . . ?
C6 O16 S17 122.33(9) . . ?
O19 S17 O18 123.22(8) . . ?
O19 S17 O16 106.08(7) . . ?
O18 S17 O16 111.59(7) . . ?
O19 S17 C20 106.41(9) . . ?
O18 S17 C20 107.40(9) . . ?
O16 S17 C20 99.47(8) . . ?
F23 C20 F22 109.74(18) . . ?
F23 C20 F21 108.94(17) . . ?
F22 C20 F21 108.79(17) . . ?
F23 C20 S17 109.30(15) . . ?
F22 C20 S17 109.65(14) . . ?
F21 C20 S17 110.40(13) . . ?

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
O9 C1 N2 C3 -0.31(16) . . . . ?
C10 C1 N2 C3 177.34(14) . . . . ?
C1 N2 C3 C8 0.07(16) . . . . ?
C1 N2 C3 C4 -179.06(16) . . . . ?
C8 C3 C4 C5 0.1(2) . . . . ?
N2 C3 C4 C5 179.12(15) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C7 -0.4(2) . . . . ?
C4 C5 C6 O16 -174.40(13) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
O16 C6 C7 C8 174.66(13) . . . . ?
C6 C7 C8 O9 -179.60(14) . . . . ?
C6 C7 C8 C3 -0.7(2) . . . . ?
C4 C3 C8 O9 179.42(13) . . . . ?
N2 C3 C8 O9 0.18(16) . . . . ?
C4 C3 C8 C7 0.3(2) . . . . ?
N2 C3 C8 C7 -178.93(14) . . . . ?
C7 C8 O9 C1 178.73(15) . . . . ?
C3 C8 O9 C1 -0.33(15) . . . . ?
N2 C1 O9 C8 0.41(16) . . . . ?
C10 C1 O9 C8 -177.49(12) . . . . ?
N2 C1 C10 C15 178.97(15) . . . . ?
O9 C1 C10 C15 -3.4(2) . . . . ?
N2 C1 C10 C11 -3.8(2) . . . . ?
O9 C1 C10 C11 173.85(13) . . . . ?
C15 C10 C11 C12 0.4(2) . . . . ?
C1 C10 C11 C12 -176.95(14) . . . . ?
C10 C11 C12 C13 1.4(2) . . . . ?
C11 C12 C13 C14 -1.8(2) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C13 C14 C15 C10 1.4(2) . . . . ?
C11 C10 C15 C14 -1.7(2) . . . . ?
C1 C10 C15 C14 175.49(14) . . . . ?
C7 C6 O16 S17 70.83(17) . . . . ?
C5 C6 O16 S17 -114.75(14) . . . . ?
C6 O16 S17 O19 -152.74(12) . . . . ?
C6 O16 S17 O18 -16.08(14) . . . . ?
C6 O16 S17 C20 97.00(13) . . . . ?
O19 S17 C20 F23 69.79(17) . . . . ?
O18 S17 C20 F23 -63.91(16) . . . . ?
O16 S17 C20 F23 179.78(15) . . . . ?
O19 S17 C20 F22 -50.55(16) . . . . ?
O18 S17 C20 F22 175.75(13) . . . . ?
O16 S17 C20 F22 59.44(15) . . . . ?
O19 S17 C20 F21 -170.40(13) . . . . ?
O18 S17 C20 F21 55.90(16) . . . . ?
O16 S17 C20 F21 -60.41(16) . . . . ?

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.054


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
