# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_BB_a
_database_code_depnum_ccdc_archive 'CCDC 1914707'
loop_
_audit_author_name
_audit_author_address
'Monish Arbaz Ansari'
;Banaras Hindu University
India
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N O3 S'
_chemical_formula_sum            'C18 H15 N O3 S'
_chemical_formula_weight         325.37

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      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   8.5498(6)
_cell_length_b                   9.8965(8)
_cell_length_c                   10.4980(8)
_cell_angle_alpha                86.670(2)
_cell_angle_beta                 77.284(2)
_cell_angle_gamma                65.193(2)
_cell_volume                     785.94(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9992
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      27.69

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.220
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19125
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.688
_diffrn_reflns_theta_max         28.197
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3289
_reflns_number_gt                2638
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+0.2203P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3289
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.2406(2) 0.93997(18) 0.06465(19) 0.0550(4) Uani 1 1 d . . . . .
H1 H 0.2645 0.9059 -0.0213 0.066 Uiso 1 1 calc R U . . .
C2 C 0.0910(3) 1.0671(2) 0.1117(2) 0.0674(5) Uani 1 1 d . . . . .
H2 H 0.0155 1.1190 0.0568 0.081 Uiso 1 1 calc R U . . .
C3 C 0.0532(3) 1.1171(2) 0.2374(3) 0.0748(6) Uani 1 1 d . . . . .
H3 H -0.0494 1.2014 0.2690 0.090 Uiso 1 1 calc R U . . .
C4 C 0.1668(3) 1.0427(2) 0.3175(2) 0.0790(6) Uani 1 1 d . . . . .
H4 H 0.1418 1.0777 0.4033 0.095 Uiso 1 1 calc R U . . .
C5 C 0.3192(3) 0.9155(2) 0.2715(2) 0.0650(5) Uani 1 1 d . . . . .
H5 H 0.3966 0.8661 0.3259 0.078 Uiso 1 1 calc R U . . .
C6 C 0.3549(2) 0.86325(17) 0.14522(17) 0.0466(4) Uani 1 1 d . . . . .
C7 C 0.6081(3) 0.7310(2) -0.03806(19) 0.0649(5) Uani 1 1 d . . . . .
H6 H 0.6272 0.8211 -0.0532 0.078 Uiso 1 1 calc R U . . .
H7 H 0.5431 0.7239 -0.1004 0.078 Uiso 1 1 calc R U . . .
C8 C 0.7799(3) 0.5981(2) -0.0527(2) 0.0768(6) Uani 1 1 d . . . . .
H9 H 0.8675 0.6238 -0.0285 0.092 Uiso 1 1 calc R U . . .
H8 H 0.8225 0.5594 -0.1425 0.092 Uiso 1 1 calc R U . . .
C9 C 0.5466(2) 0.59682(17) 0.14729(16) 0.0468(4) Uani 1 1 d . . . . .
C10 C 0.4456(2) 0.56689(18) 0.25481(17) 0.0513(4) Uani 1 1 d . . . . .
H10 H 0.3425 0.6445 0.2974 0.062 Uiso 1 1 calc R U . . .
C11 C 0.4917(2) 0.42131(18) 0.30449(16) 0.0475(4) Uani 1 1 d . . . . .
C12 C 0.3724(2) 0.39916(17) 0.42381(15) 0.0451(4) Uani 1 1 d . . . . .
C13 C 0.3942(2) 0.25393(19) 0.45255(18) 0.0579(5) Uani 1 1 d . . . . .
H11 H 0.4785 0.1734 0.3988 0.069 Uiso 1 1 calc R U . . .
C14 C 0.2879(2) 0.23427(19) 0.56204(17) 0.0548(4) Uani 1 1 d . . . . .
C15 C 0.1574(4) 0.1439(3) 0.7291(3) 0.1039(9) Uani 1 1 d . . . . .
H13 H 0.0688 0.1070 0.7287 0.125 Uiso 1 1 calc R U . . .
H12 H 0.2147 0.0998 0.8007 0.125 Uiso 1 1 calc R U . . .
C16 C 0.1652(3) 0.3491(2) 0.64331(18) 0.0630(5) Uani 1 1 d . . . . .
C17 C 0.1413(4) 0.4919(2) 0.6184(2) 0.0948(9) Uani 1 1 d . . . . .
H14 H 0.0572 0.5710 0.6738 0.114 Uiso 1 1 calc R U . . .
C18 C 0.2476(3) 0.5146(2) 0.50683(19) 0.0716(6) Uani 1 1 d . . . . .
H15 H 0.2340 0.6113 0.4875 0.086 Uiso 1 1 calc R U . . .
N1 N 0.51037(17) 0.73395(15) 0.09496(14) 0.0506(3) Uani 1 1 d . . . . .
O1 O 0.62492(16) 0.31151(13) 0.25074(13) 0.0639(4) Uani 1 1 d . . . . .
O2 O 0.2830(2) 0.10269(15) 0.60998(16) 0.0894(5) Uani 1 1 d . . . . .
O3 O 0.0777(2) 0.29742(18) 0.74663(15) 0.0927(5) Uani 1 1 d . . . . .
S1 S 0.73935(6) 0.46092(5) 0.05531(5) 0.06078(18) 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 C2 1.381(3) . ?
C1 C6 1.383(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.358(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.423(2) . ?
C7 N1 1.456(2) . ?
C7 C8 1.488(3) . ?
C7 H6 0.9700 . ?
C7 H7 0.9700 . ?
C8 S1 1.815(2) . ?
C8 H9 0.9700 . ?
C8 H8 0.9700 . ?
C9 C10 1.362(2) . ?
C9 N1 1.369(2) . ?
C9 S1 1.7459(16) . ?
C10 C11 1.425(2) . ?
C10 H10 0.9300 . ?
C11 O1 1.2434(19) . ?
C11 C12 1.500(2) . ?
C12 C18 1.374(2) . ?
C12 C13 1.393(2) . ?
C13 C14 1.360(2) . ?
C13 H11 0.9300 . ?
C14 C16 1.356(3) . ?
C14 O2 1.382(2) . ?
C15 O3 1.384(3) . ?
C15 O2 1.408(3) . ?
C15 H13 0.9700 . ?
C15 H12 0.9700 . ?
C16 C17 1.359(3) . ?
C16 O3 1.377(2) . ?
C17 C18 1.386(3) . ?
C17 H14 0.9300 . ?
C18 H15 0.9300 . ?

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
C2 C1 C6 120.01(19) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C3 C2 C1 120.68(19) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.69(19) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.61(19) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 119.48(16) . . ?
C5 C6 N1 120.95(15) . . ?
C1 C6 N1 119.55(16) . . ?
N1 C7 C8 106.88(15) . . ?
N1 C7 H6 110.3 . . ?
C8 C7 H6 110.3 . . ?
N1 C7 H7 110.3 . . ?
C8 C7 H7 110.3 . . ?
H6 C7 H7 108.6 . . ?
C7 C8 S1 106.34(12) . . ?
C7 C8 H9 110.5 . . ?
S1 C8 H9 110.5 . . ?
C7 C8 H8 110.5 . . ?
S1 C8 H8 110.5 . . ?
H9 C8 H8 108.7 . . ?
C10 C9 N1 125.47(15) . . ?
C10 C9 S1 123.46(12) . . ?
N1 C9 S1 111.05(11) . . ?
C9 C10 C11 122.52(15) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
O1 C11 C10 122.38(15) . . ?
O1 C11 C12 118.88(14) . . ?
C10 C11 C12 118.72(14) . . ?
C18 C12 C13 119.20(15) . . ?
C18 C12 C11 122.94(15) . . ?
C13 C12 C11 117.83(15) . . ?
C14 C13 C12 117.59(16) . . ?
C14 C13 H11 121.2 . . ?
C12 C13 H11 121.2 . . ?
C16 C14 C13 122.69(16) . . ?
C16 C14 O2 108.95(16) . . ?
C13 C14 O2 128.36(17) . . ?
O3 C15 O2 109.91(17) . . ?
O3 C15 H13 109.7 . . ?
O2 C15 H13 109.7 . . ?
O3 C15 H12 109.7 . . ?
O2 C15 H12 109.7 . . ?
H13 C15 H12 108.2 . . ?
C14 C16 C17 121.13(17) . . ?
C14 C16 O3 110.45(16) . . ?
C17 C16 O3 128.43(18) . . ?
C16 C17 C18 117.16(18) . . ?
C16 C17 H14 121.4 . . ?
C18 C17 H14 121.4 . . ?
C12 C18 C17 122.23(17) . . ?
C12 C18 H15 118.9 . . ?
C17 C18 H15 118.9 . . ?
C9 N1 C6 122.97(13) . . ?
C9 N1 C7 114.70(14) . . ?
C6 N1 C7 119.47(13) . . ?
C14 O2 C15 105.19(16) . . ?
C16 O3 C15 105.26(16) . . ?
C9 S1 C8 92.02(8) . . ?

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
C6 C1 C2 C3 -0.9(3) . . . . ?
C1 C2 C3 C4 1.6(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 1.5(3) . . . . ?
C4 C5 C6 N1 179.56(17) . . . . ?
C2 C1 C6 C5 -0.7(3) . . . . ?
C2 C1 C6 N1 -178.81(15) . . . . ?
N1 C7 C8 S1 30.1(2) . . . . ?
N1 C9 C10 C11 -179.64(16) . . . . ?
S1 C9 C10 C11 2.0(3) . . . . ?
C9 C10 C11 O1 -1.9(3) . . . . ?
C9 C10 C11 C12 179.84(16) . . . . ?
O1 C11 C12 C18 164.42(18) . . . . ?
C10 C11 C12 C18 -17.3(3) . . . . ?
O1 C11 C12 C13 -13.6(2) . . . . ?
C10 C11 C12 C13 164.67(16) . . . . ?
C18 C12 C13 C14 0.7(3) . . . . ?
C11 C12 C13 C14 178.86(16) . . . . ?
C12 C13 C14 C16 -0.8(3) . . . . ?
C12 C13 C14 O2 179.22(18) . . . . ?
C13 C14 C16 C17 0.5(4) . . . . ?
O2 C14 C16 C17 -179.6(2) . . . . ?
C13 C14 C16 O3 -179.45(19) . . . . ?
O2 C14 C16 O3 0.5(2) . . . . ?
C14 C16 C17 C18 -0.1(4) . . . . ?
O3 C16 C17 C18 179.8(2) . . . . ?
C13 C12 C18 C17 -0.4(3) . . . . ?
C11 C12 C18 C17 -178.4(2) . . . . ?
C16 C17 C18 C12 0.0(4) . . . . ?
C10 C9 N1 C6 -2.8(3) . . . . ?
S1 C9 N1 C6 175.75(13) . . . . ?
C10 C9 N1 C7 -163.50(18) . . . . ?
S1 C9 N1 C7 15.04(19) . . . . ?
C5 C6 N1 C9 60.6(2) . . . . ?
C1 C6 N1 C9 -121.34(18) . . . . ?
C5 C6 N1 C7 -139.56(19) . . . . ?
C1 C6 N1 C7 38.5(2) . . . . ?
C8 C7 N1 C9 -30.1(2) . . . . ?
C8 C7 N1 C6 168.44(16) . . . . ?
C16 C14 O2 C15 -3.4(3) . . . . ?
C13 C14 O2 C15 176.6(2) . . . . ?
O3 C15 O2 C14 5.1(3) . . . . ?
C14 C16 O3 C15 2.6(3) . . . . ?
C17 C16 O3 C15 -177.3(3) . . . . ?
O2 C15 O3 C16 -4.8(3) . . . . ?
C10 C9 S1 C8 -177.90(17) . . . . ?
N1 C9 S1 C8 3.52(15) . . . . ?
C7 C8 S1 C9 -19.81(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H11 O2 0.93 2.63 3.435(2) 145.7 2_656
C7 H7 O1 0.97 2.48 3.450(3) 175.5 2_665
C7 H7 O1 0.97 2.48 3.450(3) 175.5 2_665
C13 H11 O2 0.93 2.63 3.435(2) 145.7 2_656

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1922170'
loop_
_audit_author_name
_audit_author_address
'Monish Arbaz Ansari'
;Banaras Hindu University
India
;
_audit_update_record             
;
2019-06-11 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 F3 N O S'
_chemical_formula_weight         362.38

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'
F F 0.0171 0.0103 '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                   11.2395(13)
_cell_length_b                   9.4816(9)
_cell_length_c                   32.652(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3479.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      27.80

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             1496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.222
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22688
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.879
_diffrn_reflns_theta_max         23.822
_diffrn_reflns_theta_full        23.822
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2657
_reflns_number_gt                2369
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0695P)²+5.2714P] 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         2657
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1486
_refine_ls_wR_factor_gt          0.1417
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_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 0.41779(6) 0.13868(8) 0.51540(2) 0.0422(3) Uani 1 1 d . . . . .
N1 N 0.21544(19) 0.1450(2) 0.56080(7) 0.0387(6) Uani 1 1 d . . . . .
O1 O 0.58706(19) 0.2419(3) 0.56601(7) 0.0750(8) Uani 1 1 d . . . . .
C10 C 0.3339(2) 0.1734(3) 0.55932(8) 0.0336(6) Uani 1 1 d . . . . .
C11 C 0.3929(2) 0.2300(3) 0.59298(8) 0.0389(6) Uani 1 1 d . . . . .
H11 H 0.3479 0.2495 0.6162 0.047 Uiso 1 1 calc R U . . .
C5 C 0.1466(2) 0.1916(3) 0.59549(8) 0.0387(6) Uani 1 1 d . . . . .
C16 C 0.6609(3) 0.4345(3) 0.70508(9) 0.0493(8) Uani 1 1 d . . . . .
C13 C 0.5642(2) 0.3199(3) 0.63414(9) 0.0428(7) Uani 1 1 d . . . . .
C12 C 0.5161(2) 0.2603(3) 0.59470(9) 0.0430(7) Uani 1 1 d . . . . .
C17 C 0.7052(3) 0.4725(4) 0.66735(10) 0.0580(9) Uani 1 1 d . . . . .
H17 H 0.7669 0.5376 0.6656 0.070 Uiso 1 1 calc R U . . .
C4 C 0.1446(3) 0.1141(3) 0.63124(9) 0.0496(8) Uani 1 1 d . . . . .
H4 H 0.1891 0.0318 0.6335 0.060 Uiso 1 1 calc R U . . .
C15 C 0.5686(3) 0.3385(4) 0.70759(9) 0.0551(8) Uani 1 1 d . . . . .
H15 H 0.5392 0.3116 0.7330 0.066 Uiso 1 1 calc R U . . .
C7 C 0.1436(3) 0.0773(4) 0.52856(9) 0.0512(8) Uani 1 1 d . . . . .
H7A H 0.1002 0.1498 0.5139 0.061 Uiso 1 1 calc R U . . .
H7B H 0.0856 0.0159 0.5415 0.061 Uiso 1 1 calc R U . . .
C6 C 0.0797(3) 0.3128(4) 0.59224(10) 0.0552(8) Uani 1 1 d . . . . .
H6 H 0.0814 0.3653 0.5682 0.066 Uiso 1 1 calc R U . . .
C18 C 0.6582(3) 0.4145(4) 0.63227(9) 0.0557(9) Uani 1 1 d . . . . .
H18 H 0.6899 0.4391 0.6069 0.067 Uiso 1 1 calc R U . . .
C9 C 0.3087(3) 0.0798(3) 0.47857(9) 0.0473(7) Uani 1 1 d . . . . .
H9A H 0.2726 0.1611 0.4655 0.057 Uiso 1 1 calc R U . . .
H9B H 0.3479 0.0245 0.4575 0.057 Uiso 1 1 calc R U . . .
C14 C 0.5202(3) 0.2827(3) 0.67225(9) 0.0505(8) Uani 1 1 d . . . . .
H14 H 0.4573 0.2193 0.6741 0.061 Uiso 1 1 calc R U . . .
C1 C 0.0103(3) 0.3564(4) 0.62469(12) 0.0694(10) Uani 1 1 d . . . . .
H1 H -0.0351 0.4380 0.6224 0.083 Uiso 1 1 calc R U . . .
F2 F 0.8259(3) 0.5176(5) 0.74115(9) 0.1530(16) Uani 1 1 d . . . . .
F3 F 0.6942(5) 0.4319(5) 0.77533(8) 0.194(2) Uani 1 1 d . . . . .
C8 C 0.2138(3) -0.0074(3) 0.49838(9) 0.0516(8) Uani 1 1 d . . . . .
H8A H 0.1608 -0.0440 0.4775 0.062 Uiso 1 1 calc R U . . .
H8B H 0.2502 -0.0869 0.5123 0.062 Uiso 1 1 calc R U . . .
C3 C 0.0756(3) 0.1602(4) 0.66377(10) 0.0614(9) Uani 1 1 d . . . . .
H3 H 0.0752 0.1097 0.6882 0.074 Uiso 1 1 calc R U . . .
C2 C 0.0080(3) 0.2797(4) 0.66020(11) 0.0659(10) Uani 1 1 d . . . . .
H2 H -0.0395 0.3089 0.6819 0.079 Uiso 1 1 calc R U . . .
F1 F 0.6754(5) 0.6244(4) 0.74907(12) 0.187(2) Uani 1 1 d . . . . .
C19 C 0.7108(4) 0.4992(4) 0.74282(11) 0.0686(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
S1 C10 1.748(3) . ?
S1 C9 1.806(3) . ?
N1 C10 1.359(3) . ?
N1 C5 1.442(3) . ?
N1 C7 1.474(4) . ?
O1 C12 1.243(3) . ?
C10 C11 1.392(4) . ?
C11 C12 1.415(4) . ?
C11 H11 0.9300 . ?
C5 C4 1.379(4) . ?
C5 C6 1.378(4) . ?
C16 C17 1.377(4) . ?
C16 C15 1.382(5) . ?
C16 C19 1.486(4) . ?
C13 C18 1.388(4) . ?
C13 C14 1.385(4) . ?
C13 C12 1.507(4) . ?
C17 C18 1.376(4) . ?
C17 H17 0.9300 . ?
C4 C3 1.386(5) . ?
C4 H4 0.9300 . ?
C15 C14 1.381(4) . ?
C15 H15 0.9300 . ?
C7 C8 1.496(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 C1 1.379(5) . ?
C6 H6 0.9300 . ?
C18 H18 0.9300 . ?
C9 C8 1.496(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C14 H14 0.9300 . ?
C1 C2 1.369(5) . ?
C1 H1 0.9300 . ?
F2 C19 1.307(5) . ?
F3 C19 1.253(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C3 C2 1.369(5) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
F1 C19 1.269(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
C10 S1 C9 103.78(13) . . ?
C10 N1 C5 119.5(2) . . ?
C10 N1 C7 126.7(2) . . ?
C5 N1 C7 113.6(2) . . ?
N1 C10 C11 121.0(2) . . ?
N1 C10 S1 121.4(2) . . ?
C11 C10 S1 117.60(19) . . ?
C10 C11 C12 125.2(3) . . ?
C10 C11 H11 117.4 . . ?
C12 C11 H11 117.4 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 N1 120.7(3) . . ?
C6 C5 N1 119.2(3) . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 C19 119.8(3) . . ?
C15 C16 C19 120.4(3) . . ?
C18 C13 C14 118.4(3) . . ?
C18 C13 C12 118.6(3) . . ?
C14 C13 C12 123.0(3) . . ?
O1 C12 C11 124.7(3) . . ?
O1 C12 C13 117.8(2) . . ?
C11 C12 C13 117.5(2) . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C14 C15 C16 119.9(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
N1 C7 C8 114.5(2) . . ?
N1 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C17 C18 C13 120.9(3) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C8 C9 S1 111.5(2) . . ?
C8 C9 H9A 109.3 . . ?
S1 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
S1 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C2 C1 C6 120.2(3) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C7 C8 C9 111.4(3) . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
F3 C19 F1 107.1(4) . . ?
F3 C19 F2 104.5(4) . . ?
F1 C19 F2 101.1(4) . . ?
F3 C19 C16 115.9(4) . . ?
F1 C19 C16 113.7(4) . . ?
F2 C19 C16 113.2(3) . . ?

_refine_diff_density_max         0.709
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.051

