# Electronic Supplementary Material (ESI) for Energy & Environmental Science.
# This journal is © The Royal Society of Chemistry 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_x15334
_database_code_depnum_ccdc_archive 'CCDC 1451232'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2014). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2016-07-11 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT911_x15334              
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L=  0.600        147 Report
RESPONSE: Crystal twinned by non-merohedry.  
;
# Added during the CSD deposition process: Monday 11 July 2016 05:35 PM
# end Validation Reply Form


_audit_creation_method           'SHELXL-2014/7 and CIFFIX'

_shelx_SHELXL_version_number     2014/7

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 N S, B F4'
_chemical_formula_sum            'C14 H13 B F4 N S'
_chemical_formula_weight         314.12

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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 '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                   7.1696(1)
_cell_length_b                   17.3429(4)
_cell_length_c                   11.1994(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.232(1)
_cell_angle_gamma                90
_cell_volume                     1337.04(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      4.11
_cell_measurement_theta_max      68.26

_exptl_crystal_description       'triangular prism-shaped rod'
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.526
_shelx_estimated_absorpt_T_min   0.719
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.492
_exptl_absorpt_correction_T_max  0.893
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2008b)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus rotating anode'
_diffrn_measurement_device_type  'Bruker X8 Proteum diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 5.6
_diffrn_reflns_number            2446
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.839
_diffrn_reflns_theta_max         68.250
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.960

_reflns_number_total             2446
_reflns_number_gt                2251
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
; 
_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        'APEX2 (Bruker-AXS, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          'Refined as a 2-component twin., Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1234P)²+0.5734P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2446
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1731
_refine_ls_wR_factor_gt          0.1630
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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
S1 S 0.28663(9) 0.58749(4) 0.48642(6) 0.0195(3) Uani 1 1 d . . . . .
N1 N 0.3497(3) 0.42389(13) 0.6093(2) 0.0195(5) Uani 1 1 d . . . . .
C1 C 0.4201(4) 0.48713(16) 0.6848(3) 0.0200(6) Uani 1 1 d . . . . .
C2 C 0.5198(4) 0.47726(18) 0.8120(3) 0.0240(6) Uani 1 1 d . . . . .
H2 H 0.5311 0.4271 0.8474 0.029 Uiso 1 1 calc R U . . .
C3 C 0.6004(4) 0.53894(18) 0.8851(3) 0.0259(6) Uani 1 1 d . . . . .
H3 H 0.6670 0.5305 0.9701 0.031 Uiso 1 1 calc R U . . .
C4 C 0.5867(4) 0.61389(18) 0.8372(3) 0.0261(7) Uani 1 1 d . . . . .
H4 H 0.6451 0.6559 0.8886 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4874(4) 0.62577(17) 0.7143(3) 0.0234(6) Uani 1 1 d . . . . .
H5 H 0.4749 0.6765 0.6811 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4047(4) 0.56378(16) 0.6380(3) 0.0191(6) Uani 1 1 d . . . . .
C7 C 0.1953(4) 0.50022(16) 0.4234(3) 0.0196(6) Uani 1 1 d . . . . .
C8 C 0.0842(4) 0.50355(17) 0.2982(3) 0.0234(6) Uani 1 1 d . . . . .
H8 H 0.0630 0.5517 0.2562 0.028 Uiso 1 1 calc R U . . .
C9 C 0.0061(4) 0.4374(2) 0.2363(3) 0.0264(6) Uani 1 1 d . . . . .
H9 H -0.0665 0.4393 0.1512 0.032 Uiso 1 1 calc R U . . .
C10 C 0.0350(4) 0.36770(17) 0.3002(3) 0.0254(6) Uani 1 1 d . . . . .
H10 H -0.0207 0.3221 0.2579 0.031 Uiso 1 1 calc R U . . .
C11 C 0.1419(4) 0.36274(16) 0.4229(3) 0.0229(6) Uani 1 1 d . . . . .
H11 H 0.1572 0.3143 0.4641 0.027 Uiso 1 1 calc R U . . .
C12 C 0.2293(4) 0.42935(17) 0.4880(3) 0.0199(6) Uani 1 1 d . . . . .
C13 C 0.3855(4) 0.34577(17) 0.6667(3) 0.0232(6) Uani 1 1 d . . . . .
H13A H 0.5142 0.3450 0.7290 0.028 Uiso 1 1 calc R U . . .
H13B H 0.3874 0.3074 0.6016 0.028 Uiso 1 1 calc R U . . .
C14 C 0.2296(5) 0.32354(19) 0.7293(3) 0.0309(7) Uani 1 1 d . . . . .
H14A H 0.2248 0.3623 0.7920 0.046 Uiso 1 1 calc R U . . .
H14B H 0.2608 0.2731 0.7693 0.046 Uiso 1 1 calc R U . . .
H14C H 0.1031 0.3209 0.6667 0.046 Uiso 1 1 calc R U . . .
B1 B 0.0895(5) 0.67503(19) 0.0683(3) 0.0231(7) Uani 1 1 d . . . . .
F1 F 0.0045(3) 0.60236(10) 0.05317(16) 0.0293(4) Uani 1 1 d . . . . .
F2 F 0.1652(2) 0.69055(11) 0.19453(16) 0.0296(4) Uani 1 1 d . . . . .
F3 F -0.0495(2) 0.73054(10) 0.01432(16) 0.0293(4) Uani 1 1 d . . . . .
F4 F 0.2394(3) 0.67722(11) 0.01078(18) 0.0357(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
S1 C7 1.720(3) . ?
S1 C6 1.721(3) . ?
N1 C1 1.390(4) . ?
N1 C12 1.394(4) . ?
N1 C13 1.490(3) . ?
C1 C2 1.414(4) . ?
C1 C6 1.422(4) . ?
C2 C3 1.373(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.406(4) . ?
C7 C12 1.413(4) . ?
C8 C9 1.377(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.416(4) . ?
C11 H11 0.9500 . ?
C13 C14 1.526(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
B1 F1 1.389(4) . ?
B1 F2 1.391(4) . ?
B1 F3 1.396(4) . ?
B1 F4 1.399(4) . ?

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
C7 S1 C6 102.73(13) . . ?
C1 N1 C12 124.0(2) . . ?
C1 N1 C13 117.8(2) . . ?
C12 N1 C13 117.8(2) . . ?
N1 C1 C2 120.8(3) . . ?
N1 C1 C6 122.4(2) . . ?
C2 C1 C6 116.7(3) . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 S1 115.3(2) . . ?
C1 C6 S1 123.6(2) . . ?
C8 C7 C12 121.0(3) . . ?
C8 C7 S1 114.7(2) . . ?
C12 C7 S1 124.3(2) . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.0(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 122.0(3) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
N1 C12 C7 122.0(3) . . ?
N1 C12 C11 120.7(3) . . ?
C7 C12 C11 117.2(3) . . ?
N1 C13 C14 111.6(2) . . ?
N1 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N1 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F1 B1 F2 109.4(2) . . ?
F1 B1 F3 109.7(2) . . ?
F2 B1 F3 109.6(2) . . ?
F1 B1 F4 109.6(2) . . ?
F2 B1 F4 109.3(2) . . ?
F3 B1 F4 109.2(2) . . ?

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
C12 N1 C1 C2 171.5(2) . . . . ?
C13 N1 C1 C2 -0.9(4) . . . . ?
C12 N1 C1 C6 -11.7(4) . . . . ?
C13 N1 C1 C6 176.0(2) . . . . ?
N1 C1 C2 C3 175.8(2) . . . . ?
C6 C1 C2 C3 -1.2(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 S1 -179.6(2) . . . . ?
N1 C1 C6 C5 -176.0(2) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
N1 C1 C6 S1 3.8(4) . . . . ?
C2 C1 C6 S1 -179.23(18) . . . . ?
C7 S1 C6 C5 -177.24(19) . . . . ?
C7 S1 C6 C1 3.0(2) . . . . ?
C6 S1 C7 C8 178.01(19) . . . . ?
C6 S1 C7 C12 -3.3(3) . . . . ?
C12 C7 C8 C9 0.1(4) . . . . ?
S1 C7 C8 C9 178.8(2) . . . . ?
C7 C8 C9 C10 1.5(4) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C1 N1 C12 C7 11.2(4) . . . . ?
C13 N1 C12 C7 -176.4(2) . . . . ?
C1 N1 C12 C11 -171.3(2) . . . . ?
C13 N1 C12 C11 1.0(3) . . . . ?
C8 C7 C12 N1 175.6(2) . . . . ?
S1 C7 C12 N1 -3.0(4) . . . . ?
C8 C7 C12 C11 -2.0(4) . . . . ?
S1 C7 C12 C11 179.46(19) . . . . ?
C10 C11 C12 N1 -175.2(2) . . . . ?
C10 C11 C12 C7 2.4(4) . . . . ?
C1 N1 C13 C14 85.6(3) . . . . ?
C12 N1 C13 C14 -87.2(3) . . . . ?

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.081



####################################################################### 
# 
# 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_x16014
_database_code_depnum_ccdc_archive 'CCDC 1492208'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2014). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2016-07-11 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           'SHELXL-2014/7 and CIFFIX'

_shelx_SHELXL_version_number     2014/7

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N O S, B F4'
_chemical_formula_sum            'C15 H15 B F4 N O S'
_chemical_formula_weight         344.15

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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'
F F 0.0727 0.0534 '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'

_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                   6.8493(2)
_cell_length_b                   10.8341(3)
_cell_length_c                   19.2816(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.004(2)
_cell_angle_gamma                90
_cell_volume                     1430.81(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    3982
_cell_measurement_theta_min      4.59
_cell_measurement_theta_max      68.00

_exptl_crystal_description       rod
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_F_000             708
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.471
_shelx_estimated_absorpt_T_min   0.589
_shelx_estimated_absorpt_T_max   0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.889
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus rotating anode'
_diffrn_measurement_device_type  'Bruker X8 Proteum diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 5.6
_diffrn_reflns_number            18466
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.291
_diffrn_reflns_theta_max         68.215
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.990

_reflns_number_total             2571
_reflns_number_gt                2177
_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        'APEX2 (Bruker-AXS, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0843P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2571
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.1226
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
N1 N 0.7718(4) 0.6327(2) 0.44375(13) 0.0204(5) Uani 1 1 d . . . . .
S1 S 0.72159(12) 0.49343(7) 0.58462(4) 0.0235(2) Uani 1 1 d . . . . .
O1 O 0.4924(3) 0.7782(2) 0.36314(12) 0.0276(5) Uani 1 1 d . . . . .
C1 C 0.7788(5) 0.5044(3) 0.44216(17) 0.0213(6) Uani 1 1 d . . . . .
C2 C 0.8160(5) 0.4399(3) 0.38000(17) 0.0242(7) Uani 1 1 d . . . . .
H2A H 0.828(6) 0.480(4) 0.337(2) 0.029 Uiso 1 1 d . U . . .
C3 C 0.8328(5) 0.3137(3) 0.37868(17) 0.0261(7) Uani 1 1 d . . . . .
H3A H 0.8600 0.2732 0.3361 0.031 Uiso 1 1 calc R U . . .
C4 C 0.8103(4) 0.2439(3) 0.43924(17) 0.0254(7) Uani 1 1 d . . . . .
H4A H 0.8228 0.1566 0.4379 0.030 Uiso 1 1 calc R U . . .
C5 C 0.7698(5) 0.3031(3) 0.50050(17) 0.0248(7) Uani 1 1 d . . . . .
H5A H 0.7508 0.2561 0.5415 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7563(4) 0.4323(3) 0.50319(16) 0.0217(6) Uani 1 1 d . . . . .
C7 C 0.7057(4) 0.6496(3) 0.56863(15) 0.0227(6) Uani 1 1 d . . . . .
C8 C 0.6685(5) 0.7223(3) 0.62711(16) 0.0254(7) Uani 1 1 d . . . . .
H8A H 0.6566 0.6842 0.6713 0.030 Uiso 1 1 calc R U . . .
C9 C 0.6490(5) 0.8474(3) 0.62144(18) 0.0291(7) Uani 1 1 d . . . . .
H9A H 0.6242 0.8964 0.6613 0.035 Uiso 1 1 calc R U . . .
C10 C 0.6662(5) 0.9025(3) 0.55597(18) 0.0266(7) Uani 1 1 d . . . . .
H10A H 0.6505 0.9893 0.5516 0.032 Uiso 1 1 calc R U . . .
C11 C 0.7055(5) 0.8329(3) 0.49780(17) 0.0244(6) Uani 1 1 d . . . . .
H11A H 0.712(5) 0.879(3) 0.454(2) 0.029 Uiso 1 1 d . U . . .
C12 C 0.7274(4) 0.7033(3) 0.50263(15) 0.0209(6) Uani 1 1 d . . . . .
C13 C 0.8146(5) 0.6979(3) 0.37761(16) 0.0234(7) Uani 1 1 d . . . . .
H13A H 0.914(6) 0.654(4) 0.356(2) 0.028 Uiso 1 1 d . U . . .
H13B H 0.857(5) 0.780(4) 0.389(2) 0.028 Uiso 1 1 d . U . . .
C14 C 0.6399(5) 0.7074(3) 0.33013(16) 0.0268(7) Uani 1 1 d . . . . .
H14A H 0.6784 0.7473 0.2860 0.032 Uiso 1 1 calc R U . . .
H14B H 0.5896 0.6239 0.3195 0.032 Uiso 1 1 calc R U . . .
C15 C 0.3409(5) 0.8110(3) 0.31649(18) 0.0288(7) Uani 1 1 d . . . . .
H15A H 0.2415 0.8590 0.3412 0.043 Uiso 1 1 calc R U . . .
H15B H 0.2815 0.7360 0.2975 0.043 Uiso 1 1 calc R U . . .
H15C H 0.3950 0.8606 0.2786 0.043 Uiso 1 1 calc R U . . .
B1 B -0.1246(6) 0.9999(4) 0.2847(2) 0.0272(8) Uani 1 1 d . . . . .
F1 F -0.0553(3) 0.89005(18) 0.25697(11) 0.0322(5) Uani 1 1 d . . . . .
F2 F -0.0063(3) 1.09651(19) 0.26225(11) 0.0345(5) Uani 1 1 d . . . . .
F3 F -0.1212(4) 0.99273(19) 0.35632(11) 0.0431(6) Uani 1 1 d . . . . .
F4 F -0.3149(3) 1.0171(2) 0.26102(14) 0.0473(6) 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 C1 1.391(4) . ?
N1 C12 1.403(4) . ?
N1 C13 1.487(4) . ?
S1 C6 1.721(3) . ?
S1 C7 1.723(3) . ?
O1 C15 1.419(4) . ?
O1 C14 1.419(4) . ?
C1 C2 1.411(4) . ?
C1 C6 1.421(4) . ?
C2 C3 1.372(5) . ?
C2 H2A 0.93(4) . ?
C3 C4 1.400(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.372(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.404(4) . ?
C5 H5A 0.9500 . ?
C7 C8 1.399(4) . ?
C7 C12 1.407(4) . ?
C8 C9 1.366(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.401(5) . ?
C9 H9A 0.9500 . ?
C10 C11 1.378(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.415(4) . ?
C11 H11A 0.98(4) . ?
C13 C14 1.510(5) . ?
C13 H13A 0.93(4) . ?
C13 H13B 0.96(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
B1 F3 1.384(5) . ?
B1 F1 1.388(4) . ?
B1 F2 1.392(4) . ?
B1 F4 1.393(5) . ?

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
C1 N1 C12 124.8(3) . . ?
C1 N1 C13 116.7(3) . . ?
C12 N1 C13 118.5(3) . . ?
C6 S1 C7 102.91(15) . . ?
C15 O1 C14 111.8(3) . . ?
N1 C1 C2 121.3(3) . . ?
N1 C1 C6 121.8(3) . . ?
C2 C1 C6 116.8(3) . . ?
C3 C2 C1 121.6(3) . . ?
C3 C2 H2A 116(2) . . ?
C1 C2 H2A 122(2) . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C5 C6 C1 120.7(3) . . ?
C5 C6 S1 115.3(2) . . ?
C1 C6 S1 124.0(2) . . ?
C8 C7 C12 121.0(3) . . ?
C8 C7 S1 114.8(2) . . ?
C12 C7 S1 124.1(2) . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8A 119.6 . . ?
C7 C8 H8A 119.6 . . ?
C8 C9 C10 119.1(3) . . ?
C8 C9 H9A 120.4 . . ?
C10 C9 H9A 120.4 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10A 119.4 . . ?
C9 C10 H10A 119.4 . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11A 115(2) . . ?
C12 C11 H11A 124(2) . . ?
N1 C12 C7 122.0(3) . . ?
N1 C12 C11 120.7(3) . . ?
C7 C12 C11 117.3(3) . . ?
N1 C13 C14 113.3(3) . . ?
N1 C13 H13A 107(2) . . ?
C14 C13 H13A 110(2) . . ?
N1 C13 H13B 108(2) . . ?
C14 C13 H13B 108(2) . . ?
H13A C13 H13B 111(3) . . ?
O1 C14 C13 109.2(3) . . ?
O1 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
O1 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F3 B1 F1 109.3(3) . . ?
F3 B1 F2 110.0(3) . . ?
F1 B1 F2 109.0(3) . . ?
F3 B1 F4 110.5(3) . . ?
F1 B1 F4 108.0(3) . . ?
F2 B1 F4 110.0(3) . . ?

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
C12 N1 C1 C2 177.1(3) . . . . ?
C13 N1 C1 C2 -2.8(4) . . . . ?
C12 N1 C1 C6 -5.3(5) . . . . ?
C13 N1 C1 C6 174.8(3) . . . . ?
N1 C1 C2 C3 176.7(3) . . . . ?
C6 C1 C2 C3 -1.0(5) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C3 C4 C5 C6 -1.7(5) . . . . ?
C4 C5 C6 C1 1.8(5) . . . . ?
C4 C5 C6 S1 -175.7(2) . . . . ?
N1 C1 C6 C5 -178.1(3) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
N1 C1 C6 S1 -0.8(4) . . . . ?
C2 C1 C6 S1 176.9(2) . . . . ?
C7 S1 C6 C5 -178.5(2) . . . . ?
C7 S1 C6 C1 4.1(3) . . . . ?
C6 S1 C7 C8 177.4(2) . . . . ?
C6 S1 C7 C12 -2.5(3) . . . . ?
C12 C7 C8 C9 1.1(5) . . . . ?
S1 C7 C8 C9 -178.8(3) . . . . ?
C7 C8 C9 C10 0.2(5) . . . . ?
C8 C9 C10 C11 -1.1(5) . . . . ?
C9 C10 C11 C12 0.7(5) . . . . ?
C1 N1 C12 C7 7.0(5) . . . . ?
C13 N1 C12 C7 -173.1(3) . . . . ?
C1 N1 C12 C11 -173.9(3) . . . . ?
C13 N1 C12 C11 6.0(4) . . . . ?
C8 C7 C12 N1 177.7(3) . . . . ?
S1 C7 C12 N1 -2.4(4) . . . . ?
C8 C7 C12 C11 -1.5(4) . . . . ?
S1 C7 C12 C11 178.5(2) . . . . ?
C10 C11 C12 N1 -178.6(3) . . . . ?
C10 C11 C12 C7 0.6(5) . . . . ?
C1 N1 C13 C14 83.3(3) . . . . ?
C12 N1 C13 C14 -96.6(3) . . . . ?
C15 O1 C14 C13 168.4(3) . . . . ?
N1 C13 C14 O1 62.7(4) . . . . ?

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.068



####################################################################### 
# 
# 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_k16007
_database_code_depnum_ccdc_archive 'CCDC 1492209'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2014). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2016-07-11 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           'SHELXL-2014/7 and CIFFIX'

_shelx_SHELXL_version_number     2014/7

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N O S'
_chemical_formula_sum            'C15 H15 N O S'
_chemical_formula_weight         257.34

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'
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                   8.7624(18)
_cell_length_b                   7.6786(15)
_cell_length_c                   19.134(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.37(3)
_cell_angle_gamma                90
_cell_volume                     1270.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    3184
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.241
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed-tube'
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            27500
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.158
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000

_reflns_number_total             2912
_reflns_number_gt                2331
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 2006)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0653P)²+0.5595P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2912
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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 0.50347(15) 0.24757(18) 0.34807(7) 0.0201(3) Uani 1 1 d . . . . .
S1 S 0.63842(5) 0.50085(5) 0.25760(2) 0.02264(14) Uani 1 1 d . . . . .
O1 O 0.33424(14) 0.18754(16) 0.50764(6) 0.0252(3) Uani 1 1 d . . . . .
C1 C 0.43983(17) 0.2368(2) 0.27544(8) 0.0199(3) Uani 1 1 d . . . . .
C2 C 0.32077(18) 0.1224(2) 0.24958(8) 0.0218(3) Uani 1 1 d . . . . .
H2A H 0.2851 0.0414 0.2808 0.026 Uiso 1 1 calc R U . . .
C3 C 0.25371(19) 0.1251(2) 0.17887(8) 0.0233(4) Uani 1 1 d . . . . .
H3A H 0.1689 0.0504 0.1626 0.028 Uiso 1 1 calc R U . . .
C4 C 0.30885(19) 0.2352(2) 0.13192(8) 0.0247(4) Uani 1 1 d . . . . .
H4A H 0.2630 0.2363 0.0834 0.030 Uiso 1 1 calc R U . . .
C5 C 0.43141(19) 0.3439(2) 0.15621(8) 0.0225(3) Uani 1 1 d . . . . .
H5A H 0.4725 0.4173 0.1239 0.027 Uiso 1 1 calc R U . . .
C6 C 0.49507(18) 0.3470(2) 0.22735(8) 0.0212(3) Uani 1 1 d . . . . .
C7 C 0.74223(18) 0.3791(2) 0.32733(8) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.90000(18) 0.4029(2) 0.34457(9) 0.0234(4) Uani 1 1 d . . . . .
H8A H 0.9522 0.4750 0.3158 0.028 Uiso 1 1 calc R U . . .
C9 C 0.98220(19) 0.3227(2) 0.40327(9) 0.0255(4) Uani 1 1 d . . . . .
H9A H 1.0900 0.3432 0.4162 0.031 Uiso 1 1 calc R U . . .
C10 C 0.90668(19) 0.2126(2) 0.44294(9) 0.0248(4) Uani 1 1 d . . . . .
H10A H 0.9629 0.1569 0.4835 0.030 Uiso 1 1 calc R U . . .
C11 C 0.74984(19) 0.1822(2) 0.42444(8) 0.0218(3) Uani 1 1 d . . . . .
H11A H 0.6998 0.1024 0.4512 0.026 Uiso 1 1 calc R U . . .
C12 C 0.66483(18) 0.2678(2) 0.36677(8) 0.0200(3) Uani 1 1 d . . . . .
C13 C 0.42009(18) 0.1653(2) 0.39888(8) 0.0213(3) Uani 1 1 d . . . . .
H13A H 0.4687 0.0518 0.4135 0.026 Uiso 1 1 calc R U . . .
H13B H 0.3120 0.1431 0.3762 0.026 Uiso 1 1 calc R U . . .
C14 C 0.42032(19) 0.2781(2) 0.46348(8) 0.0209(3) Uani 1 1 d . . . . .
H14A H 0.5274 0.2975 0.4880 0.025 Uiso 1 1 calc R U . . .
H14B H 0.3723 0.3924 0.4499 0.025 Uiso 1 1 calc R U . . .
C15 C 0.3113(2) 0.2885(3) 0.56655(9) 0.0304(4) Uani 1 1 d . . . . .
H15A H 0.2525 0.2209 0.5965 0.046 Uiso 1 1 calc R U . . .
H15B H 0.2538 0.3942 0.5502 0.046 Uiso 1 1 calc R U . . .
H15C H 0.4118 0.3206 0.5939 0.046 Uiso 1 1 calc R U . . .


_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 C12 1.409(2) . ?
N1 C1 1.413(2) . ?
N1 C13 1.4523(19) . ?
S1 C6 1.7526(17) . ?
S1 C7 1.7567(17) . ?
O1 C14 1.4048(18) . ?
O1 C15 1.409(2) . ?
C1 C2 1.392(2) . ?
C1 C6 1.393(2) . ?
C2 C3 1.385(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.377(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.380(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.385(2) . ?
C5 H5A 0.9500 . ?
C7 C8 1.380(2) . ?
C7 C12 1.388(2) . ?
C8 C9 1.377(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.376(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.382(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.392(2) . ?
C11 H11A 0.9500 . ?
C13 C14 1.509(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C12 N1 C1 118.37(13) . . ?
C12 N1 C13 118.11(13) . . ?
C1 N1 C13 118.16(13) . . ?
C6 S1 C7 98.45(8) . . ?
C14 O1 C15 111.67(13) . . ?
C2 C1 C6 118.00(14) . . ?
C2 C1 N1 122.64(14) . . ?
C6 C1 N1 119.35(14) . . ?
C3 C2 C1 120.80(16) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 . . ?
C4 C3 C2 120.57(16) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 119.22(15) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C4 C5 C6 120.55(16) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C1 120.74(15) . . ?
C5 C6 S1 119.25(13) . . ?
C1 C6 S1 119.90(12) . . ?
C8 C7 C12 120.69(15) . . ?
C8 C7 S1 119.08(13) . . ?
C12 C7 S1 120.14(12) . . ?
C9 C8 C7 120.44(16) . . ?
C9 C8 H8A 119.8 . . ?
C7 C8 H8A 119.8 . . ?
C10 C9 C8 119.35(16) . . ?
C10 C9 H9A 120.3 . . ?
C8 C9 H9A 120.3 . . ?
C9 C10 C11 120.67(16) . . ?
C9 C10 H10A 119.7 . . ?
C11 C10 H10A 119.7 . . ?
C10 C11 C12 120.31(15) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C7 C12 C11 118.43(15) . . ?
C7 C12 N1 119.24(14) . . ?
C11 C12 N1 122.31(15) . . ?
N1 C13 C14 111.41(13) . . ?
N1 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N1 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
O1 C14 C13 106.23(13) . . ?
O1 C14 H14A 110.5 . . ?
C13 C14 H14A 110.5 . . ?
O1 C14 H14B 110.5 . . ?
C13 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C12 N1 C1 C2 139.85(16) . . . . ?
C13 N1 C1 C2 -13.8(2) . . . . ?
C12 N1 C1 C6 -41.5(2) . . . . ?
C13 N1 C1 C6 164.77(15) . . . . ?
C6 C1 C2 C3 -3.6(2) . . . . ?
N1 C1 C2 C3 175.06(15) . . . . ?
C1 C2 C3 C4 3.3(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 -2.2(2) . . . . ?
C4 C5 C6 C1 1.9(2) . . . . ?
C4 C5 C6 S1 -174.10(13) . . . . ?
C2 C1 C6 C5 0.9(2) . . . . ?
N1 C1 C6 C5 -177.72(15) . . . . ?
C2 C1 C6 S1 176.96(12) . . . . ?
N1 C1 C6 S1 -1.7(2) . . . . ?
C7 S1 C6 C5 -149.25(13) . . . . ?
C7 S1 C6 C1 34.68(15) . . . . ?
C6 S1 C7 C8 147.95(13) . . . . ?
C6 S1 C7 C12 -35.47(15) . . . . ?
C12 C7 C8 C9 -3.1(3) . . . . ?
S1 C7 C8 C9 173.49(13) . . . . ?
C7 C8 C9 C10 2.8(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C12 -2.4(3) . . . . ?
C8 C7 C12 C11 0.6(2) . . . . ?
S1 C7 C12 C11 -175.90(12) . . . . ?
C8 C7 C12 N1 179.50(14) . . . . ?
S1 C7 C12 N1 3.0(2) . . . . ?
C10 C11 C12 C7 2.1(2) . . . . ?
C10 C11 C12 N1 -176.76(15) . . . . ?
C1 N1 C12 C7 40.8(2) . . . . ?
C13 N1 C12 C7 -165.51(14) . . . . ?
C1 N1 C12 C11 -140.37(16) . . . . ?
C13 N1 C12 C11 13.3(2) . . . . ?
C12 N1 C13 C14 67.76(18) . . . . ?
C1 N1 C13 C14 -138.48(15) . . . . ?
C15 O1 C14 C13 -173.43(14) . . . . ?
N1 C13 C14 O1 178.74(12) . . . . ?

_refine_diff_density_max         0.546
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.063



####################################################################### 
# 
# 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_k16020
_database_code_depnum_ccdc_archive 'CCDC 1492210'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2014). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2016-07-11 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           'SHELXL-2014/7 and CIFFIX'

_shelx_SHELXL_version_number     2014/7

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 N O2 S, B F4'
_chemical_formula_sum            'C17 H19 B F4 N O2 S'
_chemical_formula_weight         388.20

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'
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                   7.0364(1)
_cell_length_b                   12.4613(2)
_cell_length_c                   19.4044(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.2495(8)
_cell_angle_gamma                90
_cell_volume                     1683.82(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    4038
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       'irregular block'
_exptl_crystal_colour            red-green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             804
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.246
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed-tube'
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            44852
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.948
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000

_reflns_number_total             3864
_reflns_number_gt                3363
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 2006)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0539P)²+0.6919P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3864
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.23010(15) 0.40157(9) 0.42486(6) 0.0194(2) Uani 1 1 d . . . . .
S1 S 0.27931(5) 0.52894(3) 0.56599(2) 0.02176(10) Uani 1 1 d . . . . .
O1 O 0.48091(14) 0.26609(8) 0.34758(5) 0.0232(2) Uani 1 1 d . . . . .
O2 O 0.84317(14) 0.16462(8) 0.39393(5) 0.0239(2) Uani 1 1 d . . . . .
C1 C 0.29199(18) 0.3447(1) 0.48590(7) 0.0198(3) Uani 1 1 d . . . . .
C2 C 0.33613(19) 0.23404(11) 0.48328(7) 0.0226(3) Uani 1 1 d . . . . .
H2A H 0.3270 0.1988 0.4395 0.027 Uiso 1 1 calc R U . . .
C3 C 0.39205(19) 0.17728(11) 0.54342(7) 0.0244(3) Uani 1 1 d . . . . .
H3A H 0.4224 0.1033 0.5405 0.029 Uiso 1 1 calc R U . . .
C4 C 0.4055(2) 0.22590(11) 0.60906(7) 0.0255(3) Uani 1 1 d . . . . .
H4A H 0.4412 0.1850 0.6502 0.031 Uiso 1 1 calc R U . . .
C5 C 0.36638(19) 0.33343(11) 0.61321(7) 0.0244(3) Uani 1 1 d . . . . .
H5A H 0.3745 0.3669 0.6575 0.029 Uiso 1 1 calc R U . . .
C6 C 0.31462(18) 0.39424(11) 0.55260(7) 0.0210(3) Uani 1 1 d . . . . .
C7 C 0.22645(18) 0.57781(11) 0.48220(7) 0.0206(3) Uani 1 1 d . . . . .
C8 C 0.19778(19) 0.68903(11) 0.47743(7) 0.0237(3) Uani 1 1 d . . . . .
H8A H 0.2144 0.7315 0.5185 0.028 Uiso 1 1 calc R U . . .
C9 C 0.1458(2) 0.73724(11) 0.41377(7) 0.0245(3) Uani 1 1 d . . . . .
H9A H 0.1284 0.8128 0.4106 0.029 Uiso 1 1 calc R U . . .
C10 C 0.11885(19) 0.67339(11) 0.35349(7) 0.0240(3) Uani 1 1 d . . . . .
H10A H 0.0804 0.7062 0.3095 0.029 Uiso 1 1 calc R U . . .
C11 C 0.14722(19) 0.56421(11) 0.35712(7) 0.0216(3) Uani 1 1 d . . . . .
H11A H 0.1291 0.5229 0.3155 0.026 Uiso 1 1 calc R U . . .
C12 C 0.20290(18) 0.51229(10) 0.42174(7) 0.0196(3) Uani 1 1 d . . . . .
C13 C 0.17442(19) 0.33971(10) 0.35928(7) 0.0207(3) Uani 1 1 d . . . . .
H13A H 0.0603 0.3739 0.3323 0.025 Uiso 1 1 calc R U . . .
H13B H 0.1376 0.2661 0.3714 0.025 Uiso 1 1 calc R U . . .
C14 C 0.33180(19) 0.33262(11) 0.31373(7) 0.0223(3) Uani 1 1 d . . . . .
H14A H 0.2800 0.3019 0.2678 0.027 Uiso 1 1 calc R U . . .
H14B H 0.3826 0.4051 0.3062 0.027 Uiso 1 1 calc R U . . .
C15 C 0.6091(2) 0.22879(12) 0.30215(7) 0.0258(3) Uani 1 1 d . . . . .
H15A H 0.7022 0.2859 0.2950 0.031 Uiso 1 1 calc R U . . .
H15B H 0.5363 0.2096 0.2563 0.031 Uiso 1 1 calc R U . . .
C16 C 0.7132(2) 0.13222(11) 0.33460(7) 0.0256(3) Uani 1 1 d . . . . .
H16A H 0.6199 0.0800 0.3486 0.031 Uiso 1 1 calc R U . . .
H16B H 0.7846 0.0970 0.3004 0.031 Uiso 1 1 calc R U . . .
C17 C 0.9092(2) 0.07501(12) 0.43552(8) 0.0285(3) Uani 1 1 d . . . . .
H17A H 1.0035 0.0988 0.4747 0.043 Uiso 1 1 calc R U . . .
H17B H 0.9693 0.0233 0.4073 0.043 Uiso 1 1 calc R U . . .
H17C H 0.8005 0.0410 0.4533 0.043 Uiso 1 1 calc R U . . .
B1 B 0.2217(2) 0.00111(13) 0.29759(8) 0.0251(3) Uani 1 1 d . . . . .
F1 F 0.14635(13) 0.10402(7) 0.28888(5) 0.0325(2) Uani 1 1 d . . . . .
F2 F 0.07237(13) -0.07365(7) 0.28375(5) 0.0342(2) Uani 1 1 d . . . . .
F3 F 0.31158(14) -0.01221(8) 0.36563(5) 0.0382(2) Uani 1 1 d . . . . .
F4 F 0.35315(15) -0.01383(9) 0.25133(6) 0.0449(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
N1 C12 1.3931(17) . ?
N1 C1 1.3953(16) . ?
N1 C13 1.4912(16) . ?
S1 C6 1.7220(14) . ?
S1 C7 1.7259(13) . ?
O1 C14 1.4220(16) . ?
O1 C15 1.4266(16) . ?
O2 C17 1.4165(16) . ?
O2 C16 1.4221(16) . ?
C1 C2 1.4161(18) . ?
C1 C6 1.4221(18) . ?
C2 C3 1.3730(19) . ?
C2 H2A 0.9500 . ?
C3 C4 1.401(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.373(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.4026(18) . ?
C5 H5A 0.9500 . ?
C7 C8 1.4017(19) . ?
C7 C12 1.4194(18) . ?
C8 C9 1.3751(19) . ?
C8 H8A 0.9500 . ?
C9 C10 1.4049(19) . ?
C9 H9A 0.9500 . ?
C10 C11 1.3754(19) . ?
C10 H10A 0.9500 . ?
C11 C12 1.4154(18) . ?
C11 H11A 0.9500 . ?
C13 C14 1.5154(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.4997(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
B1 F1 1.3887(18) . ?
B1 F3 1.3895(18) . ?
B1 F4 1.3908(19) . ?
B1 F2 1.4010(18) . ?

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
C12 N1 C1 124.34(11) . . ?
C12 N1 C13 117.21(10) . . ?
C1 N1 C13 118.28(11) . . ?
C6 S1 C7 102.60(6) . . ?
C14 O1 C15 113.24(10) . . ?
C17 O2 C16 110.96(11) . . ?
N1 C1 C2 120.49(12) . . ?
N1 C1 C6 122.19(12) . . ?
C2 C1 C6 117.32(12) . . ?
C3 C2 C1 120.58(13) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C2 C3 C4 121.56(13) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
C5 C4 C3 119.18(13) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
C4 C5 C6 120.55(13) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C1 120.69(12) . . ?
C5 C6 S1 115.21(10) . . ?
C1 C6 S1 124.1(1) . . ?
C8 C7 C12 121.03(12) . . ?
C8 C7 S1 114.87(10) . . ?
C12 C7 S1 124.02(10) . . ?
C9 C8 C7 120.57(13) . . ?
C9 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C8 C9 C10 119.15(13) . . ?
C8 C9 H9A 120.4 . . ?
C10 C9 H9A 120.4 . . ?
C11 C10 C9 121.09(13) . . ?
C11 C10 H10A 119.5 . . ?
C9 C10 H10A 119.5 . . ?
C10 C11 C12 121.14(12) . . ?
C10 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
N1 C12 C11 120.67(12) . . ?
N1 C12 C7 122.33(12) . . ?
C11 C12 C7 117.00(12) . . ?
N1 C13 C14 113.79(10) . . ?
N1 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
N1 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
O1 C14 C13 108.48(10) . . ?
O1 C14 H14A 110.0 . . ?
C13 C14 H14A 110.0 . . ?
O1 C14 H14B 110.0 . . ?
C13 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
O1 C15 C16 108.43(11) . . ?
O1 C15 H15A 110.0 . . ?
C16 C15 H15A 110.0 . . ?
O1 C15 H15B 110.0 . . ?
C16 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
O2 C16 C15 109.31(11) . . ?
O2 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
O2 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
F1 B1 F3 109.86(12) . . ?
F1 B1 F4 108.82(13) . . ?
F3 B1 F4 110.06(12) . . ?
F1 B1 F2 109.15(12) . . ?
F3 B1 F2 109.23(12) . . ?
F4 B1 F2 109.70(12) . . ?

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
C12 N1 C1 C2 -172.99(12) . . . . ?
C13 N1 C1 C2 12.02(18) . . . . ?
C12 N1 C1 C6 6.62(19) . . . . ?
C13 N1 C1 C6 -168.37(11) . . . . ?
N1 C1 C2 C3 -178.22(12) . . . . ?
C6 C1 C2 C3 2.15(19) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C2 C3 C4 C5 -1.6(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C1 3.3(2) . . . . ?
C4 C5 C6 S1 -177.52(11) . . . . ?
N1 C1 C6 C5 176.28(12) . . . . ?
C2 C1 C6 C5 -4.10(19) . . . . ?
N1 C1 C6 S1 -2.86(18) . . . . ?
C2 C1 C6 S1 176.75(10) . . . . ?
C7 S1 C6 C5 178.21(10) . . . . ?
C7 S1 C6 C1 -2.60(13) . . . . ?
C6 S1 C7 C8 -177.62(10) . . . . ?
C6 S1 C7 C12 5.53(13) . . . . ?
C12 C7 C8 C9 0.1(2) . . . . ?
S1 C7 C8 C9 -176.91(11) . . . . ?
C7 C8 C9 C10 1.0(2) . . . . ?
C8 C9 C10 C11 -1.3(2) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C1 N1 C12 C11 177.40(12) . . . . ?
C13 N1 C12 C11 -7.56(17) . . . . ?
C1 N1 C12 C7 -3.49(19) . . . . ?
C13 N1 C12 C7 171.55(12) . . . . ?
C10 C11 C12 N1 179.60(12) . . . . ?
C10 C11 C12 C7 0.45(19) . . . . ?
C8 C7 C12 N1 -179.90(12) . . . . ?
S1 C7 C12 N1 -3.23(18) . . . . ?
C8 C7 C12 C11 -0.76(19) . . . . ?
S1 C7 C12 C11 175.91(10) . . . . ?
C12 N1 C13 C14 86.85(14) . . . . ?
C1 N1 C13 C14 -97.80(13) . . . . ?
C15 O1 C14 C13 163.18(11) . . . . ?
N1 C13 C14 O1 69.30(13) . . . . ?
C14 O1 C15 C16 -160.30(11) . . . . ?
C17 O2 C16 C15 165.72(11) . . . . ?
O1 C15 C16 O2 -69.93(14) . . . . ?

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.050



