# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_NN1091R_0m
_database_code_depnum_ccdc_archive 'CCDC 1533274'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 F3 N O'
_chemical_formula_weight         231.22

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   5.0215(5)
_cell_length_b                   8.6681(9)
_cell_length_c                   12.6928(13)
_cell_angle_alpha                80.3440(10)
_cell_angle_beta                 83.0720(10)
_cell_angle_gamma                88.4000(10)
_cell_volume                     540.66(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    90
_cell_measurement_reflns_used    2998
_cell_measurement_theta_min      2.384
_cell_measurement_theta_max      28.769

_exptl_crystal_description       tip

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.127
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            2564
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_av_R_equivalents  0.0070
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.639
_diffrn_reflns_theta_max         25.011
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.565
_diffrn_reflns_point_group_measured_fraction_full 0.553
_reflns_number_total             2146
_reflns_number_gt                2141
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.163
_reflns_Friedel_fraction_max     0.159
_reflns_Friedel_fraction_full    0.155

_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       'APEX2 (Bruker AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXT (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

_computing_molecular_graphics    'XSHELL (Bruker AXS,2002)'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'


_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'


_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)+(0.0271P)²+0.1434P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_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_abs_structure_details 
;
 Flack x determined using 300 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.17(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2146
_refine_ls_number_parameters     291
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0210
_refine_ls_wR_factor_ref         0.0545
_refine_ls_wR_factor_gt          0.0544
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.086
_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 0.4649(4) 1.0961(3) 0.48848(19) 0.0221(4) Uani 1 1 d . . . . .
H1 H 0.5085 1.0107 0.4449 0.026 Uiso 1 1 calc R U . . .
C2 C 0.5260(4) 1.0442(2) 0.60134(18) 0.0206(4) Uani 1 1 d . . . . .
H2A H 0.4894 1.1319 0.6421 0.025 Uiso 1 1 calc R U . . .
H2B H 0.7192 1.0175 0.6004 0.025 Uiso 1 1 calc R U . . .
C3 C 0.3603(4) 0.9016(2) 0.65965(17) 0.0171(4) Uani 1 1 d . . . . .
H3 H 0.1665 0.9293 0.6561 0.021 Uiso 1 1 calc R U . . .
C4 C 0.4029(4) 0.8645(2) 0.77738(17) 0.0180(4) Uani 1 1 d . . . . .
C5 C 0.6068(4) 0.7659(3) 0.81350(18) 0.0247(5) Uani 1 1 d . . . . .
H5 H 0.7210 0.7167 0.7635 0.030 Uiso 1 1 calc R U . . .
C6 C 0.6475(4) 0.7376(3) 0.92131(19) 0.0284(5) Uani 1 1 d . . . . .
H6 H 0.7873 0.6694 0.9452 0.034 Uiso 1 1 calc R U . . .
C7 C 0.4824(4) 0.8097(3) 0.99276(18) 0.0246(5) Uani 1 1 d . . . . .
C8 C 0.2763(5) 0.9069(3) 0.9611(2) 0.0306(5) Uani 1 1 d . . . . .
H8 H 0.1628 0.9551 1.0118 0.037 Uiso 1 1 calc R U . . .
C9 C 0.2375(4) 0.9333(3) 0.85280(19) 0.0260(5) Uani 1 1 d . . . . .
H9 H 0.0947 0.9999 0.8299 0.031 Uiso 1 1 calc R U . . .
C10 C 0.2283(4) 0.6888(2) 0.57084(15) 0.0147(4) Uani 1 1 d . . . . .
C11 C 0.3227(4) 0.5522(2) 0.51711(18) 0.0208(4) Uani 1 1 d . . . . .
H11A H 0.1922 0.4674 0.5381 0.031 Uiso 1 1 calc R U . . .
H11B H 0.4970 0.5156 0.5393 0.031 Uiso 1 1 calc R U . . .
H11C H 0.3407 0.5846 0.4388 0.031 Uiso 1 1 calc R U . . .
C12 C -0.0019(4) 0.4447(3) 0.28402(18) 0.0199(4) Uani 1 1 d . . . . .
H12 H 0.0066 0.3425 0.3336 0.024 Uiso 1 1 calc R U . . .
C13 C -0.1124(4) 0.4229(3) 0.18289(17) 0.0197(4) Uani 1 1 d . . . . .
H13A H -0.1052 0.5237 0.1326 0.024 Uiso 1 1 calc R U . . .
H13B H -0.3028 0.3916 0.2005 0.024 Uiso 1 1 calc R U . . .
C14 C 0.0444(4) 0.2984(2) 0.12763(16) 0.0160(4) Uani 1 1 d . . . . .
H14 H 0.2398 0.3194 0.1257 0.019 Uiso 1 1 calc R U . . .
C15 C -0.0155(4) 0.3084(2) 0.01233(16) 0.0158(4) Uani 1 1 d . . . . .
C16 C 0.1331(4) 0.4110(2) -0.06819(18) 0.0225(5) Uani 1 1 d . . . . .
H16 H 0.2722 0.4700 -0.0499 0.027 Uiso 1 1 calc R U . . .
C17 C 0.0822(5) 0.4287(3) -0.17475(19) 0.0274(5) Uani 1 1 d . . . . .
H17 H 0.1844 0.4986 -0.2294 0.033 Uiso 1 1 calc R U . . .
C18 C -0.1212(4) 0.3418(3) -0.19870(17) 0.0239(5) Uani 1 1 d . . . . .
C19 C -0.2720(4) 0.2389(3) -0.12192(18) 0.0239(5) Uani 1 1 d . . . . .
H19 H -0.4096 0.1797 -0.1411 0.029 Uiso 1 1 calc R U . . .
C20 C -0.2192(4) 0.2231(3) -0.01572(17) 0.0210(4) Uani 1 1 d . . . . .
H20 H -0.3232 0.1532 0.0384 0.025 Uiso 1 1 calc R U . . .
C21 C 0.1783(4) 0.0516(2) 0.23725(16) 0.0159(4) Uani 1 1 d . . . . .
C22 C 0.0811(4) -0.1025(2) 0.30181(18) 0.0226(5) Uani 1 1 d . . . . .
H22A H 0.2090 -0.1855 0.2862 0.034 Uiso 1 1 calc R U . . .
H22B H -0.0948 -0.1259 0.2825 0.034 Uiso 1 1 calc R U . . .
H22C H 0.0659 -0.0963 0.3787 0.034 Uiso 1 1 calc R U . . .
F1 F 0.6070(3) 1.22783(16) 0.44319(11) 0.0330(3) Uani 1 1 d . . . . .
F2 F 0.1991(2) 1.13892(16) 0.48808(11) 0.0304(3) Uani 1 1 d . . . . .
F3 F 0.5257(3) 0.78499(17) 1.09740(11) 0.0374(3) Uani 1 1 d . . . . .
F4 F 0.2493(2) 0.51009(16) 0.25776(11) 0.0281(3) Uani 1 1 d . . . . .
F5 F -0.1548(2) 0.55047(15) 0.33363(11) 0.0270(3) Uani 1 1 d . . . . .
F6 F -0.1743(3) 0.35736(18) -0.30257(11) 0.0369(3) Uani 1 1 d . . . . .
N1 N 0.4194(3) 0.76788(19) 0.60397(14) 0.0168(4) Uani 1 1 d . . . . .
H1A H 0.5876 0.7380 0.5916 0.020 Uiso 1 1 calc R U . . .
N2 N -0.0100(3) 0.14310(19) 0.19128(14) 0.0161(3) Uani 1 1 d . . . . .
H2 H -0.1752 0.1078 0.1999 0.019 Uiso 1 1 calc R U . . .
O1 O -0.0113(3) 0.72733(18) 0.58308(12) 0.0206(3) Uani 1 1 d . . . . .
O2 O 0.4156(3) 0.09073(17) 0.22830(13) 0.0222(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 F1 1.368(2) . ?
C1 F2 1.376(2) . ?
C1 C2 1.493(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.540(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.461(3) . ?
C3 C4 1.515(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.387(3) . ?
C4 C9 1.391(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.371(3) . ?
C6 H6 0.9500 . ?
C7 F3 1.352(3) . ?
C7 C8 1.371(3) . ?
C8 C9 1.391(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 O1 1.238(2) . ?
C10 N1 1.341(3) . ?
C10 C11 1.501(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 F5 1.365(3) . ?
C12 F4 1.378(2) . ?
C12 C13 1.500(3) . ?
C12 H12 1.0000 . ?
C13 C14 1.533(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N2 1.463(3) . ?
C14 C15 1.517(3) . ?
C14 H14 1.0000 . ?
C15 C20 1.392(3) . ?
C15 C16 1.393(3) . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.378(3) . ?
C17 H17 0.9500 . ?
C18 F6 1.360(3) . ?
C18 C19 1.373(3) . ?
C19 C20 1.389(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 O2 1.235(2) . ?
C21 N2 1.342(3) . ?
C21 C22 1.505(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N1 H1A 0.8800 . ?
N2 H2 0.8800 . ?

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
F1 C1 F2 105.57(17) . . ?
F1 C1 C2 109.97(17) . . ?
F2 C1 C2 110.06(18) . . ?
F1 C1 H1 110.4 . . ?
F2 C1 H1 110.4 . . ?
C2 C1 H1 110.4 . . ?
C1 C2 C3 112.81(17) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 C4 112.51(16) . . ?
N1 C3 C2 110.26(16) . . ?
C4 C3 C2 111.21(16) . . ?
N1 C3 H3 107.5 . . ?
C4 C3 H3 107.5 . . ?
C2 C3 H3 107.5 . . ?
C5 C4 C9 118.0(2) . . ?
C5 C4 C3 122.29(18) . . ?
C9 C4 C3 119.74(18) . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 118.9(2) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
F3 C7 C8 119.1(2) . . ?
F3 C7 C6 118.9(2) . . ?
C8 C7 C6 122.0(2) . . ?
C7 C8 C9 118.4(2) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C4 C9 C8 121.5(2) . . ?
C4 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
O1 C10 N1 121.87(18) . . ?
O1 C10 C11 122.14(18) . . ?
N1 C10 C11 115.99(16) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
F5 C12 F4 105.52(16) . . ?
F5 C12 C13 110.17(17) . . ?
F4 C12 C13 109.18(17) . . ?
F5 C12 H12 110.6 . . ?
F4 C12 H12 110.6 . . ?
C13 C12 H12 110.6 . . ?
C12 C13 C14 111.95(16) . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N2 C14 C15 112.39(16) . . ?
N2 C14 C13 109.86(17) . . ?
C15 C14 C13 111.38(15) . . ?
N2 C14 H14 107.7 . . ?
C15 C14 H14 107.7 . . ?
C13 C14 H14 107.7 . . ?
C20 C15 C16 118.67(19) . . ?
C20 C15 C14 122.58(17) . . ?
C16 C15 C14 118.71(17) . . ?
C17 C16 C15 121.34(19) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 117.9(2) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
F6 C18 C19 118.5(2) . . ?
F6 C18 C17 118.9(2) . . ?
C19 C18 C17 122.6(2) . . ?
C18 C19 C20 118.7(2) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C19 C20 C15 120.73(19) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
O2 C21 N2 122.62(18) . . ?
O2 C21 C22 121.82(18) . . ?
N2 C21 C22 115.56(17) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 N1 C3 122.78(15) . . ?
C10 N1 H1A 118.6 . . ?
C3 N1 H1A 118.6 . . ?
C21 N2 C14 123.56(16) . . ?
C21 N2 H2 118.2 . . ?
C14 N2 H2 118.2 . . ?

_refine_diff_density_max         0.118
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.029

_shelxl_version_number           2013-2



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_NN734_0m
_database_code_depnum_ccdc_archive 'CCDC 1533276'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            DBXS
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H19 B F6 S'
_chemical_formula_weight         380.19

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'
B B 0.0013 0.0007 '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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.8754(11)
_cell_length_b                   14.2531(12)
_cell_length_c                   17.5717(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3475.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    90
_cell_measurement_reflns_used    9884
_cell_measurement_theta_min      2.354
_cell_measurement_theta_max      28.932

_exptl_crystal_description       prism

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.243
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            15395
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.318
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3065
_reflns_number_gt                2832
_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       'APEX2 (Bruker AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXT (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

_computing_molecular_graphics    'XSHELL (Bruker AXS,2002)'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'


_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'


_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)+(0.0302P)²+2.8611P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_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         3065
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0720
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_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
B1 B 0.34182(12) 0.58501(11) 0.00492(9) 0.0207(3) Uani 1 1 d . . . . .
C1 C 0.50262(10) 0.30523(9) 0.51920(8) 0.0188(3) Uani 1 1 d . . . . .
C2 C 0.42769(10) 0.29436(10) 0.46783(8) 0.0208(3) Uani 1 1 d . . . . .
H2 H 0.3775 0.2507 0.4776 0.025 Uiso 1 1 calc R U . . .
C3 C 0.42665(10) 0.34824(10) 0.40151(8) 0.0233(3) Uani 1 1 d . . . . .
C4 C 0.50079(11) 0.41270(11) 0.39079(8) 0.0266(3) Uani 1 1 d . . . . .
H4 H 0.5008 0.4507 0.3463 0.032 Uiso 1 1 calc R U . . .
C5 C 0.57443(11) 0.42295(10) 0.44305(9) 0.0269(3) Uani 1 1 d . . . . .
H5 H 0.6234 0.4681 0.4339 0.032 Uiso 1 1 calc R U . . .
C6 C 0.57860(10) 0.36878(10) 0.50878(8) 0.0225(3) Uani 1 1 d . . . . .
C7 C 0.66011(11) 0.37884(11) 0.56465(9) 0.0299(3) Uani 1 1 d . . . . .
H7A H 0.7076 0.4233 0.5446 0.045 Uiso 1 1 calc R U . . .
H7B H 0.6908 0.3177 0.5725 0.045 Uiso 1 1 calc R U . . .
H7C H 0.6350 0.4021 0.6132 0.045 Uiso 1 1 calc R U . . .
C8 C 0.34714(11) 0.33598(12) 0.34417(9) 0.0300(4) Uani 1 1 d . . . . .
H8A H 0.3387 0.2691 0.3331 0.045 Uiso 1 1 calc R U . . .
H8B H 0.3639 0.3694 0.2972 0.045 Uiso 1 1 calc R U . . .
H8C H 0.2870 0.3615 0.3648 0.045 Uiso 1 1 calc R U . . .
C9 C 0.47304(10) 0.30370(10) 0.67918(8) 0.0205(3) Uani 1 1 d . . . . .
C10 C 0.39013(10) 0.35784(9) 0.67151(8) 0.0215(3) Uani 1 1 d . . . . .
H10 H 0.3543 0.3567 0.6254 0.026 Uiso 1 1 calc R U . . .
C11 C 0.36018(12) 0.41377(10) 0.73206(9) 0.0274(3) Uani 1 1 d . . . . .
C12 C 0.41677(13) 0.41384(11) 0.79775(9) 0.0341(4) Uani 1 1 d . . . . .
H12 H 0.3983 0.4524 0.8394 0.041 Uiso 1 1 calc R U . . .
C13 C 0.49885(12) 0.35956(12) 0.80404(9) 0.0340(4) Uani 1 1 d . . . . .
H13 H 0.5353 0.3619 0.8498 0.041 Uiso 1 1 calc R U . . .
C14 C 0.52962(11) 0.30151(11) 0.74518(9) 0.0268(3) Uani 1 1 d . . . . .
C15 C 0.27044(13) 0.47223(11) 0.72645(10) 0.0381(4) Uani 1 1 d . . . . .
H15A H 0.2876 0.5362 0.7112 0.057 Uiso 1 1 calc R U . . .
H15B H 0.2381 0.4737 0.7760 0.057 Uiso 1 1 calc R U . . .
H15C H 0.2270 0.4449 0.6885 0.057 Uiso 1 1 calc R U . . .
C16 C 0.61845(12) 0.24204(13) 0.75422(10) 0.0369(4) Uani 1 1 d . . . . .
H16A H 0.6692 0.2654 0.7204 0.055 Uiso 1 1 calc R U . . .
H16B H 0.6033 0.1769 0.7410 0.055 Uiso 1 1 calc R U . . .
H16C H 0.6407 0.2450 0.8071 0.055 Uiso 1 1 calc R U . . .
C17 C 0.42029(10) 0.14099(10) 0.59529(8) 0.0220(3) Uani 1 1 d . . . . .
H17 H 0.4286 0.1020 0.5484 0.026 Uiso 1 1 calc R U . . .
F1 F 0.43444(7) 0.09001(6) 0.65847(5) 0.0299(2) Uani 1 1 d . . . . .
F2 F 0.33200(6) 0.17793(6) 0.59883(5) 0.0270(2) Uani 1 1 d . . . . .
F3 F 0.33641(7) 0.56126(8) -0.07148(5) 0.0409(3) Uani 1 1 d . . . . .
F4 F 0.30186(7) 0.51428(7) 0.04835(6) 0.0417(3) Uani 1 1 d . . . . .
F5 F 0.43876(6) 0.59509(7) 0.02415(5) 0.0337(2) Uani 1 1 d . . . . .
F6 F 0.29424(8) 0.66792(7) 0.01728(7) 0.0476(3) Uani 1 1 d . . . . .
S1 S 0.51495(2) 0.23370(2) 0.60183(2) 0.01906(10) 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
B1 F6 1.3710(19) . ?
B1 F4 1.3807(18) . ?
B1 F3 1.3866(19) . ?
B1 F5 1.3942(18) . ?
C1 C2 1.385(2) . ?
C1 C6 1.402(2) . ?
C1 S1 1.7824(14) . ?
C2 C3 1.396(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(2) . ?
C3 C8 1.504(2) . ?
C4 C5 1.382(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.504(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.392(2) . ?
C9 C14 1.401(2) . ?
C9 S1 1.7835(14) . ?
C10 C11 1.393(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(2) . ?
C11 C15 1.502(2) . ?
C12 C13 1.381(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(2) . ?
C13 H13 0.9500 . ?
C14 C16 1.504(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 F2 1.3348(17) . ?
C17 F1 1.3413(16) . ?
C17 S1 1.8666(14) . ?
C17 H17 1.0000 . ?

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
F6 B1 F4 110.39(13) . . ?
F6 B1 F3 109.74(13) . . ?
F4 B1 F3 109.58(13) . . ?
F6 B1 F5 109.72(13) . . ?
F4 B1 F5 109.19(12) . . ?
F3 B1 F5 108.18(12) . . ?
C2 C1 C6 123.47(13) . . ?
C2 C1 S1 122.60(11) . . ?
C6 C1 S1 113.81(11) . . ?
C1 C2 C3 119.35(13) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 117.94(13) . . ?
C4 C3 C8 121.87(13) . . ?
C2 C3 C8 120.19(13) . . ?
C5 C4 C3 121.76(13) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 121.62(14) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 115.84(13) . . ?
C5 C6 C7 121.36(13) . . ?
C1 C6 C7 122.80(13) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 123.76(13) . . ?
C10 C9 S1 120.39(11) . . ?
C14 C9 S1 115.83(11) . . ?
C9 C10 C11 119.34(14) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 117.66(15) . . ?
C10 C11 C15 121.00(15) . . ?
C12 C11 C15 121.34(14) . . ?
C13 C12 C11 121.97(14) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C14 121.77(15) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C9 115.48(14) . . ?
C13 C14 C16 120.52(15) . . ?
C9 C14 C16 124.00(14) . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F2 C17 F1 108.03(11) . . ?
F2 C17 S1 111.32(9) . . ?
F1 C17 S1 103.27(9) . . ?
F2 C17 H17 111.3 . . ?
F1 C17 H17 111.3 . . ?
S1 C17 H17 111.3 . . ?
C1 S1 C9 105.64(7) . . ?
C1 S1 C17 106.69(7) . . ?
C9 S1 C17 102.33(6) . . ?

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.040

_shelxl_version_number           2013-2



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
