# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xxx
_database_code_depnum_ccdc_archive 'CCDC 1556460'
_audit_update_record             
;
2017-06-16 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H10 F N O S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C16 H10 F N O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         283.32
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   9.1286(18)
_cell_length_b                   9.271(3)
_cell_length_c                   9.583(4)
_cell_angle_alpha                89.47(2)
_cell_angle_beta                 78.65(2)
_cell_angle_gamma                63.696(13)
_cell_volume                     710.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    856
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      25.4
_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.240
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_T_max  0.946

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_reflns_number            4746
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         25.43
_reflns_number_total             2396
_reflns_number_gt                1717
_reflns_threshold_expression     >2sigma(I)

_diffrn_reflns_theta_full        25.43
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 0.915
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'


#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0534P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    Constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2396
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1111
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.034

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S Uani 0.42894(7) 0.39701(7) 0.86950(6) 1.000 0.0639(2) . .
F1 F Uani 0.25533(18) 0.2552(2) 0.25481(16) 1.000 0.0946(6) . .
O2 O Uani 0.21954(19) 0.60819(19) 1.06911(16) 1.000 0.0737(6) . .
N1 N Uani 0.6793(2) 0.1866(3) 0.6375(2) 1.000 0.0849(9) . .
C1 C Uani 0.2191(3) 0.5218(3) 0.5441(2) 1.000 0.0616(8) . .
C2 C Uani 0.2205(3) 0.4669(3) 0.4094(3) 1.000 0.0695(9) . .
C3 C Uani 0.2534(3) 0.3099(3) 0.3869(2) 1.000 0.0608(8) . .
C4 C Uani 0.2866(3) 0.2045(3) 0.4904(3) 1.000 0.0624(9) . .
C5 C Uani 0.2874(3) 0.2593(2) 0.6230(2) 1.000 0.0544(8) . .
C6 C Uani 0.2533(2) 0.4190(2) 0.6520(2) 1.000 0.0435(6) . .
C7 C Uani 0.2467(2) 0.4828(2) 0.7955(2) 1.000 0.0449(7) . .
C8 C Uani 0.1097(2) 0.6068(2) 0.8707(2) 1.000 0.0511(7) . .
C9 C Uani 0.1017(3) 0.6777(3) 1.0098(2) 1.000 0.0505(7) . .
C10 C Uani -0.0428(2) 0.8328(2) 1.0772(2) 1.000 0.0487(7) . .
C11 C Uani -0.1862(3) 0.9085(3) 1.0233(2) 1.000 0.0607(8) . .
C12 C Uani -0.3171(3) 1.0521(3) 1.0926(3) 1.000 0.0736(10) . .
C13 C Uani -0.3033(3) 1.1214(3) 1.2119(3) 1.000 0.0761(10) . .
C14 C Uani -0.1607(3) 1.0469(3) 1.2660(3) 1.000 0.0706(9) . .
C15 C Uani -0.0310(3) 0.9038(3) 1.1986(2) 1.000 0.0589(8) . .
C16 C Uani 0.5717(3) 0.2730(3) 0.7245(3) 1.000 0.0621(8) . .
H1 H Uiso 0.19480 0.62930 0.56230 1.000 0.0740 calc R
H2 H Uiso 0.19960 0.53550 0.33660 1.000 0.0830 calc R
H4 H Uiso 0.30820 0.09790 0.47150 1.000 0.0750 calc R
H5 H Uiso 0.31100 0.18870 0.69420 1.000 0.0650 calc R
H8 H Uiso 0.01440 0.65040 0.83260 1.000 0.0610 calc R
H11 H Uiso -0.19490 0.86350 0.94090 1.000 0.0730 calc R
H12 H Uiso -0.41450 1.10140 1.05770 1.000 0.0880 calc R
H13 H Uiso -0.39010 1.21880 1.25650 1.000 0.0910 calc R
H14 H Uiso -0.15210 1.09310 1.34770 1.000 0.0850 calc R
H15 H Uiso 0.06530 0.85430 1.23490 1.000 0.0710 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.785(2) . . yes
S1 C16 1.715(3) . . yes
F1 C3 1.362(3) . . yes
O2 C9 1.231(3) . . yes
N1 C16 1.138(4) . . yes
C1 C2 1.388(4) . . no
C1 C6 1.386(3) . . no
C2 C3 1.360(4) . . no
C3 C4 1.367(4) . . no
C4 C5 1.375(4) . . no
C5 C6 1.390(3) . . no
C6 C7 1.482(3) . . no
C7 C8 1.338(3) . . no
C8 C9 1.466(3) . . no
C9 C10 1.492(3) . . no
C10 C11 1.385(3) . . no
C10 C15 1.387(3) . . no
C11 C12 1.391(4) . . no
C12 C13 1.370(4) . . no
C13 C14 1.379(4) . . no
C14 C15 1.379(4) . . no
C1 H1 0.9300 . . no
C2 H2 0.9300 . . no
C4 H4 0.9300 . . no
C5 H5 0.9300 . . no
C8 H8 0.9300 . . no
C11 H11 0.9300 . . no
C12 H12 0.9300 . . no
C13 H13 0.9300 . . no
C14 H14 0.9300 . . no
C15 H15 0.9300 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C16 99.78(12) . . . yes
C2 C1 C6 121.1(2) . . . no
C1 C2 C3 118.1(2) . . . no
F1 C3 C2 118.4(2) . . . yes
F1 C3 C4 118.8(2) . . . yes
C2 C3 C4 122.9(2) . . . no
C3 C4 C5 118.7(2) . . . no
C4 C5 C6 120.81(18) . . . no
C1 C6 C5 118.51(18) . . . no
C1 C6 C7 119.55(17) . . . no
C5 C6 C7 121.91(16) . . . no
S1 C7 C6 119.39(14) . . . yes
S1 C7 C8 118.29(15) . . . yes
C6 C7 C8 122.29(18) . . . no
C7 C8 C9 123.6(2) . . . no
O2 C9 C8 118.4(2) . . . yes
O2 C9 C10 120.19(19) . . . yes
C8 C9 C10 121.4(2) . . . no
C9 C10 C11 122.92(19) . . . no
C9 C10 C15 118.0(2) . . . no
C11 C10 C15 119.10(19) . . . no
C10 C11 C12 119.9(2) . . . no
C11 C12 C13 120.4(3) . . . no
C12 C13 C14 120.1(2) . . . no
C13 C14 C15 119.9(3) . . . no
C10 C15 C14 120.7(2) . . . no
S1 C16 N1 172.3(3) . . . yes
C2 C1 H1 120.00 . . . no
C6 C1 H1 119.00 . . . no
C1 C2 H2 121.00 . . . no
C3 C2 H2 121.00 . . . no
C3 C4 H4 121.00 . . . no
C5 C4 H4 121.00 . . . no
C4 C5 H5 120.00 . . . no
C6 C5 H5 120.00 . . . no
C7 C8 H8 118.00 . . . no
C9 C8 H8 118.00 . . . no
C10 C11 H11 120.00 . . . no
C12 C11 H11 120.00 . . . no
C11 C12 H12 120.00 . . . no
C13 C12 H12 120.00 . . . no
C12 C13 H13 120.00 . . . no
C14 C13 H13 120.00 . . . no
C13 C14 H14 120.00 . . . no
C15 C14 H14 120.00 . . . no
C10 C15 H15 120.00 . . . no
C14 C15 H15 120.00 . . . no

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
C16 S1 C7 C8 -170.26(17) . . . . no
C16 S1 C7 C6 7.67(18) . . . . no
C2 C1 C6 C7 -178.6(2) . . . . no
C2 C1 C6 C5 -0.7(4) . . . . no
C6 C1 C2 C3 1.2(4) . . . . no
C1 C2 C3 F1 -179.9(3) . . . . no
C1 C2 C3 C4 -0.7(5) . . . . no
C2 C3 C4 C5 -0.2(5) . . . . no
F1 C3 C4 C5 178.9(3) . . . . no
C3 C4 C5 C6 0.7(4) . . . . no
C4 C5 C6 C7 177.5(2) . . . . no
C4 C5 C6 C1 -0.3(4) . . . . no
C1 C6 C7 S1 -121.1(2) . . . . no
C5 C6 C7 C8 -121.0(2) . . . . no
C1 C6 C7 C8 56.8(3) . . . . no
C5 C6 C7 S1 61.2(3) . . . . no
S1 C7 C8 C9 0.9(3) . . . . no
C6 C7 C8 C9 -176.96(19) . . . . no
C7 C8 C9 O2 -9.1(3) . . . . no
C7 C8 C9 C10 169.1(2) . . . . no
O2 C9 C10 C11 -173.4(2) . . . . no
O2 C9 C10 C15 7.1(3) . . . . no
C8 C9 C10 C11 8.3(3) . . . . no
C8 C9 C10 C15 -171.2(2) . . . . no
C9 C10 C11 C12 179.2(2) . . . . no
C15 C10 C11 C12 -1.3(3) . . . . no
C9 C10 C15 C14 -179.8(2) . . . . no
C11 C10 C15 C14 0.7(4) . . . . no
C10 C11 C12 C13 1.7(4) . . . . no
C11 C12 C13 C14 -1.5(4) . . . . no
C12 C13 C14 C15 1.0(4) . . . . no
C13 C14 C15 C10 -0.6(4) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 O2 2.542(2) . . no
S1 O2 3.354(2) . 2_667 no
F1 H8 2.5300 . 2_566 no
F1 H11 2.4500 . 2_566 no
O2 S1 2.542(2) . . no
O2 S1 3.354(2) . 2_667 no
O2 H2 2.6400 . 1_556 no
O2 H15 2.4600 . . no
N1 C5 3.366(4) . . no
N1 H14 2.8300 . 1_644 no
N1 H4 2.7900 . 2_656 no
N1 H15 2.7200 . 2_667 no
C5 C16 2.998(4) . . no
C5 C14 3.591(4) . 2_567 no
C5 N1 3.366(4) . . no
C5 C15 3.493(4) . 2_567 no
C9 C13 3.577(4) . 2_577 no
C11 C15 3.579(4) . 2_577 no
C13 C9 3.577(4) . 2_577 no
C14 C5 3.591(4) . 2_567 no
C15 C11 3.579(4) . 2_577 no
C15 C5 3.493(4) . 2_567 no
C16 C5 2.998(4) . . no
C1 H8 2.9300 . . no
C3 H13 2.9700 . 1_644 no
C8 H11 2.7000 . . no
C8 H1 2.9300 . . no
C10 H5 3.0200 . 2_567 no
C11 H8 2.7000 . . no
C11 H5 3.0100 . 2_567 no
C12 H5 3.0000 . 2_567 no
C13 H5 3.0300 . 2_567 no
C14 H5 3.0400 . 2_567 no
C15 H5 3.0400 . 2_567 no
C16 H5 2.8800 . . no
C16 H15 3.0900 . 2_667 no
H1 C8 2.9300 . . no
H1 H14 2.5600 . 2_577 no
H2 O2 2.6400 . 1_554 no
H4 N1 2.7900 . 2_656 no
H5 C16 2.8800 . . no
H5 C10 3.0200 . 2_567 no
H5 C11 3.0100 . 2_567 no
H5 C12 3.0000 . 2_567 no
H5 C13 3.0300 . 2_567 no
H5 C14 3.0400 . 2_567 no
H5 C15 3.0400 . 2_567 no
H8 C1 2.9300 . . no
H8 C11 2.7000 . . no
H8 H11 2.1300 . . no
H8 F1 2.5300 . 2_566 no
H11 C8 2.7000 . . no
H11 H8 2.1300 . . no
H11 F1 2.4500 . 2_566 no
H13 C3 2.9700 . 1_466 no
H14 N1 2.8300 . 1_466 no
H14 H1 2.5600 . 2_577 no
H15 O2 2.4600 . . no
H15 N1 2.7200 . 2_667 no
H15 C16 3.0900 . 2_667 no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C8 H8 F1 0.9300 2.5300 3.458(3) 173.00 2_566 yes
C11 H11 F1 0.9300 2.4500 3.375(3) 171.00 2_566 yes
C15 H15 O2 0.9300 2.4600 2.770(3) 100.00 . yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
####################################################################### 
# 
# 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_xxx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1556445'
_audit_update_record             
;
2017-06-16 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 N O S2'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C17 H13 N O S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         311.42
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   14.435(4)
_cell_length_b                   7.4188(17)
_cell_length_c                   14.492(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.001(5)
_cell_angle_gamma                90
_cell_volume                     1491.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1929
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      25.4
_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Black

_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.24
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.8656
_exptl_absorpt_correction_T_max  0.9199

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_reflns_number            9681
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2679
_reflns_number_gt                2179
_reflns_threshold_expression     >2sigma(I)
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'



#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0560P)²+0.0715P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2679
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.054

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S Uani 0.21880(4) 1.17770(9) 1.08821(4) 1.000 0.0598(2) . .
S2 S Uani 0.07313(3) 1.13470(7) 0.90808(4) 1.000 0.0453(2) . .
O1 O Uani -0.28401(10) 1.0905(2) 0.51086(12) 1.000 0.0662(6) . .
N1 N Uani 0.26378(10) 1.0599(2) 0.93399(11) 1.000 0.0406(5) . .
C1 C Uani 0.42292(13) 0.9554(3) 0.87915(15) 1.000 0.0482(7) . .
C2 C Uani 0.50221(14) 0.8792(3) 0.85810(16) 1.000 0.0530(7) . .
C3 C Uani 0.49144(15) 0.7895(3) 0.77308(17) 1.000 0.0577(8) . .
C4 C Uani 0.40199(16) 0.7773(3) 0.70783(17) 1.000 0.0646(9) . .
C5 C Uani 0.32258(14) 0.8552(3) 0.72840(15) 1.000 0.0539(7) . .
C6 C Uani 0.33156(12) 0.9429(2) 0.81458(13) 1.000 0.0384(6) . .
C7 C Uani 0.24670(12) 1.0155(2) 0.84213(13) 1.000 0.0369(5) . .
C8 C Uani 0.15578(12) 1.0285(2) 0.77218(13) 1.000 0.0395(6) . .
C9 C Uani 0.07277(12) 1.0764(2) 0.79280(13) 1.000 0.0371(6) . .
C10 C Uani 0.19482(13) 1.1179(2) 0.97394(14) 1.000 0.0411(6) . .
C11 C Uani -0.02168(12) 1.0816(2) 0.72031(13) 1.000 0.0386(6) . .
C12 C Uani -0.02968(13) 1.1310(2) 0.62572(15) 1.000 0.0445(6) . .
C13 C Uani -0.11804(14) 1.1345(3) 0.55826(15) 1.000 0.0503(7) . .
C14 C Uani -0.20109(13) 1.0832(3) 0.58296(15) 1.000 0.0477(6) . .
C15 C Uani -0.19418(13) 1.0323(3) 0.67628(16) 1.000 0.0476(7) . .
C16 C Uani -0.10537(12) 1.0344(2) 0.74452(15) 1.000 0.0434(6) . .
C17 C Uani -0.36896(15) 1.0130(3) 0.52776(19) 1.000 0.0735(9) . .
H1 H Uiso 0.43070 1.01570 0.93710 1.000 0.0580 calc R
H2 H Uiso 0.56280 0.88870 0.90170 1.000 0.0640 calc R
H3 H Uiso 0.54460 0.73690 0.75940 1.000 0.0690 calc R
H4 H Uiso 0.39480 0.71690 0.65010 1.000 0.0770 calc R
H5 H Uiso 0.26250 0.84830 0.68360 1.000 0.0650 calc R
H8 H Uiso 0.15300 1.00280 0.70870 1.000 0.0470 calc R
H12 H Uiso 0.02540 1.16210 0.60790 1.000 0.0530 calc R
H13 H Uiso -0.12240 1.17110 0.49580 1.000 0.0600 calc R
H15 H Uiso -0.24900 0.99670 0.69330 1.000 0.0570 calc R
H16 H Uiso -0.10160 1.00370 0.80770 1.000 0.0520 calc R
H17A H Uiso -0.42230 1.02750 0.47160 1.000 0.1100 calc R
H17B H Uiso -0.38300 1.07270 0.58110 1.000 0.1100 calc R
H17C H Uiso -0.35840 0.88700 0.54190 1.000 0.1100 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C10 1.656(2) . . yes
S2 C9 1.7243(19) . . yes
S2 C10 1.757(2) . . yes
O1 C14 1.356(3) . . yes
O1 C17 1.435(3) . . yes
N1 C7 1.327(2) . . yes
N1 C10 1.352(2) . . yes
C1 C2 1.384(3) . . no
C1 C6 1.394(3) . . no
C2 C3 1.371(3) . . no
C3 C4 1.377(3) . . no
C4 C5 1.388(3) . . no
C5 C6 1.382(3) . . no
C6 C7 1.490(3) . . no
C7 C8 1.423(3) . . no
C8 C9 1.360(3) . . no
C9 C11 1.475(3) . . no
C11 C12 1.393(3) . . no
C11 C16 1.392(3) . . no
C12 C13 1.377(3) . . no
C13 C14 1.395(3) . . no
C14 C15 1.381(3) . . no
C15 C16 1.387(3) . . no
C1 H1 0.9300 . . no
C2 H2 0.9300 . . no
C3 H3 0.9300 . . no
C4 H4 0.9300 . . no
C5 H5 0.9300 . . no
C8 H8 0.9300 . . no
C12 H12 0.9300 . . no
C13 H13 0.9300 . . no
C15 H15 0.9300 . . no
C16 H16 0.9300 . . no
C17 H17A 0.9600 . . no
C17 H17B 0.9600 . . no
C17 H17C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 S2 C10 104.13(9) . . . yes
C14 O1 C17 117.83(18) . . . yes
C7 N1 C10 123.60(16) . . . yes
C2 C1 C6 120.78(19) . . . no
C1 C2 C3 120.0(2) . . . no
C2 C3 C4 120.1(2) . . . no
C3 C4 C5 119.9(2) . . . no
C4 C5 C6 120.86(19) . . . no
C1 C6 C5 118.27(17) . . . no
C1 C6 C7 119.45(16) . . . no
C5 C6 C7 122.21(17) . . . no
N1 C7 C6 114.80(16) . . . yes
N1 C7 C8 125.28(16) . . . yes
C6 C7 C8 119.90(16) . . . no
C7 C8 C9 123.82(17) . . . no
S2 C9 C8 120.73(14) . . . yes
S2 C9 C11 116.04(13) . . . yes
C8 C9 C11 123.23(16) . . . no
S1 C10 S2 115.23(11) . . . yes
S1 C10 N1 122.52(15) . . . yes
S2 C10 N1 122.25(14) . . . yes
C9 C11 C12 121.18(16) . . . no
C9 C11 C16 120.66(17) . . . no
C12 C11 C16 118.16(17) . . . no
C11 C12 C13 120.87(18) . . . no
C12 C13 C14 120.40(19) . . . no
O1 C14 C13 115.46(18) . . . yes
O1 C14 C15 125.16(18) . . . yes
C13 C14 C15 119.38(19) . . . no
C14 C15 C16 119.89(18) . . . no
C11 C16 C15 121.26(19) . . . no
C2 C1 H1 120.00 . . . no
C6 C1 H1 120.00 . . . no
C1 C2 H2 120.00 . . . no
C3 C2 H2 120.00 . . . no
C2 C3 H3 120.00 . . . no
C4 C3 H3 120.00 . . . no
C3 C4 H4 120.00 . . . no
C5 C4 H4 120.00 . . . no
C4 C5 H5 120.00 . . . no
C6 C5 H5 120.00 . . . no
C7 C8 H8 118.00 . . . no
C9 C8 H8 118.00 . . . no
C11 C12 H12 120.00 . . . no
C13 C12 H12 120.00 . . . no
C12 C13 H13 120.00 . . . no
C14 C13 H13 120.00 . . . no
C14 C15 H15 120.00 . . . no
C16 C15 H15 120.00 . . . no
C11 C16 H16 119.00 . . . no
C15 C16 H16 119.00 . . . no
O1 C17 H17A 110.00 . . . no
O1 C17 H17B 109.00 . . . no
O1 C17 H17C 109.00 . . . no
H17A C17 H17B 109.00 . . . no
H17A C17 H17C 109.00 . . . no
H17B C17 H17C 109.00 . . . no

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
C10 S2 C9 C8 1.12(15) . . . . no
C10 S2 C9 C11 -179.08(11) . . . . no
C9 S2 C10 S1 176.80(9) . . . . no
C9 S2 C10 N1 -3.32(16) . . . . no
C17 O1 C14 C13 170.42(19) . . . . no
C17 O1 C14 C15 -10.5(3) . . . . no
C10 N1 C7 C8 2.5(3) . . . . no
C7 N1 C10 S2 1.8(2) . . . . no
C7 N1 C10 S1 -178.29(13) . . . . no
C10 N1 C7 C6 -175.93(14) . . . . no
C6 C1 C2 C3 -0.3(3) . . . . no
C2 C1 C6 C7 175.90(18) . . . . no
C2 C1 C6 C5 -1.1(3) . . . . no
C1 C2 C3 C4 1.0(3) . . . . no
C2 C3 C4 C5 -0.3(3) . . . . no
C3 C4 C5 C6 -1.1(3) . . . . no
C4 C5 C6 C1 1.8(3) . . . . no
C4 C5 C6 C7 -175.16(18) . . . . no
C1 C6 C7 N1 -11.0(2) . . . . no
C5 C6 C7 N1 165.92(17) . . . . no
C1 C6 C7 C8 170.49(16) . . . . no
C5 C6 C7 C8 -12.6(2) . . . . no
C6 C7 C8 C9 173.39(15) . . . . no
N1 C7 C8 C9 -5.0(3) . . . . no
C7 C8 C9 S2 2.6(2) . . . . no
C7 C8 C9 C11 -177.23(14) . . . . no
C8 C9 C11 C12 -34.2(2) . . . . no
C8 C9 C11 C16 144.88(16) . . . . no
S2 C9 C11 C12 146.05(13) . . . . no
S2 C9 C11 C16 -34.92(19) . . . . no
C9 C11 C16 C15 -177.60(16) . . . . no
C12 C11 C16 C15 1.5(2) . . . . no
C9 C11 C12 C13 179.60(16) . . . . no
C16 C11 C12 C13 0.5(2) . . . . no
C11 C12 C13 C14 -1.9(3) . . . . no
C12 C13 C14 C15 1.3(3) . . . . no
C12 C13 C14 O1 -179.53(18) . . . . no
O1 C14 C15 C16 -178.40(19) . . . . no
C13 C14 C15 C16 0.7(3) . . . . no
C14 C15 C16 C11 -2.1(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 C16 3.636(2) . 3_577 no
S1 H2 3.1500 . 3_677 no
S1 H16 2.8900 . 3_577 no
S1 H12 3.1200 . 4_575 no
S2 H16 2.7200 . . no
O1 C4 3.306(3) . 3_576 no
O1 C5 3.381(3) . 3_576 no
O1 H4 2.8300 . 3_576 no
N1 H1 2.4200 . . no
N1 H17C 2.7600 . 2_556 no
C2 C4 3.504(3) . 2_656 no
C4 O1 3.306(3) . 3_576 no
C4 C2 3.504(3) . 2_646 no
C5 O1 3.381(3) . 3_576 no
C5 C15 3.535(3) . 2_546 no
C7 C14 3.506(3) . 2_546 no
C9 C16 3.493(2) . 2_556 no
C10 C14 3.556(3) . 2_556 no
C14 C10 3.556(3) . 2_546 no
C14 C7 3.506(3) . 2_556 no
C15 C5 3.535(3) . 2_556 no
C16 S1 3.636(2) . 3_577 no
C16 C9 3.493(2) . 2_546 no
C1 H17B 2.9800 . 2_546 no
C1 H1 2.9200 . 3_677 no
C1 H3 3.0200 . 2_656 no
C2 H1 2.9600 . 3_677 no
C2 H4 2.9300 . 2_656 no
C4 H17A 3.0600 . 3_576 no
C5 H8 2.6200 . . no
C8 H12 2.7800 . . no
C8 H5 2.6300 . . no
C12 H8 2.7500 . . no
C15 H17B 2.7100 . . no
C15 H17C 2.8300 . . no
C17 H15 2.5500 . . no
C17 H17A 3.0300 . 3_476 no
H1 N1 2.4200 . . no
H1 C1 2.9200 . 3_677 no
H1 C2 2.9600 . 3_677 no
H1 H1 2.3200 . 3_677 no
H1 H2 2.4200 . 3_677 no
H2 S1 3.1500 . 3_677 no
H2 H1 2.4200 . 3_677 no
H3 C1 3.0200 . 2_646 no
H4 C2 2.9300 . 2_646 no
H4 O1 2.8300 . 3_576 no
H5 C8 2.6300 . . no
H5 H8 2.0600 . . no
H8 C5 2.6200 . . no
H8 C12 2.7500 . . no
H8 H5 2.0600 . . no
H8 H12 2.3300 . . no
H12 C8 2.7800 . . no
H12 H8 2.3300 . . no
H12 S1 3.1200 . 4_574 no
H15 C17 2.5500 . . no
H15 H17B 2.2300 . . no
H15 H17C 2.4600 . . no
H16 S2 2.7200 . . no
H16 S1 2.8900 . 3_577 no
H17A C4 3.0600 . 3_576 no
H17A C17 3.0300 . 3_476 no
H17B C15 2.7100 . . no
H17B H15 2.2300 . . no
H17B C1 2.9800 . 2_556 no
H17C C15 2.8300 . . no
H17C H15 2.4600 . . no
H17C N1 2.7600 . 2_546 no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C1 H1 N1 0.9300 2.4200 2.742(3) 100.00 . yes
C16 H16 S2 0.9300 2.7200 3.073(2) 103.00 . yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
