# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_jb039
_database_code_depnum_ccdc_archive 'CCDC 1427397'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2016-01-19 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            'C14 H13 I N5 Na S'
_chemical_formula_weight         433.24

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   10.1629(3)
_cell_length_b                   10.3262(3)
_cell_length_c                   10.3488(3)
_cell_angle_alpha                109.4798(8)
_cell_angle_beta                 116.3682(8)
_cell_angle_gamma                102.2525(9)
_cell_volume                     829.69(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    7857
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.43

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    2.084
_shelx_estimated_absorpt_T_min   0.705
_shelx_estimated_absorpt_T_max   0.732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6497
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(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            8711
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_av_R_equivalents  0.0109
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.313
_diffrn_reflns_theta_max         28.425
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             4062
_reflns_number_gt                3897
_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_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)+(0.0237P)²+0.3038P] 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         4062
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0176
_refine_ls_R_factor_gt           0.0167
_refine_ls_wR_factor_ref         0.0439
_refine_ls_wR_factor_gt          0.0434
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.002
_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
I1 I 0.75968(2) 0.04125(2) 0.56392(2) 0.03518(4) Uani 1 1 d . . . . .
S1 S 0.60155(5) 0.60958(4) 0.27252(5) 0.03222(8) Uani 1 1 d . . . . .
Na1 Na 0.52228(8) 0.19303(7) 0.46150(7) 0.03443(13) Uani 1 1 d . . . . .
N1 N 0.59578(15) 0.37739(13) 0.37772(15) 0.0280(2) Uani 1 1 d . . . . .
N2 N 0.72441(16) 0.45065(15) 0.69839(16) 0.0331(3) Uani 1 1 d . . . . .
N3 N 0.39042(15) 0.08347(14) 0.16271(15) 0.0306(2) Uani 1 1 d . . . . .
N007 N 0.50880(16) 0.42240(14) 0.14498(16) 0.0326(3) Uani 1 1 d . . . . .
N008 N 0.65440(18) 0.64023(15) 0.45951(17) 0.0361(3) Uani 1 1 d . . . . .
C1 C 0.65872(17) 0.52481(16) 0.48652(17) 0.0274(3) Uani 1 1 d . . . . .
C2 C 0.51721(16) 0.33691(16) 0.21526(17) 0.0268(3) Uani 1 1 d . . . . .
C3 C 0.73999(17) 0.56564(17) 0.66494(17) 0.0286(3) Uani 1 1 d . . . . .
C4 C 0.83017(19) 0.71758(18) 0.7873(2) 0.0358(3) Uani 1 1 d . . . . .
H4A H 0.8381 0.7962 0.7591 0.043 Uiso 1 1 calc R U . . .
C5 C 0.9081(2) 0.7514(2) 0.9512(2) 0.0413(4) Uani 1 1 d . . . . .
H5A H 0.9692 0.8539 1.0376 0.050 Uiso 1 1 calc R U . . .
C6 C 0.8957(2) 0.6344(2) 0.9869(2) 0.0427(4) Uani 1 1 d . . . . .
H6A H 0.9503 0.6545 1.0982 0.051 Uiso 1 1 calc R U . . .
C7 C 0.8024(2) 0.4868(2) 0.8577(2) 0.0401(3) Uani 1 1 d . . . . .
H7A H 0.7930 0.4066 0.8834 0.048 Uiso 1 1 calc R U . . .
C8 C 0.41963(16) 0.16930(16) 0.09775(17) 0.0272(3) Uani 1 1 d . . . . .
C9 C 0.3610(2) 0.11054(19) -0.06852(19) 0.0365(3) Uani 1 1 d . . . . .
H9A H 0.3868 0.1747 -0.1096 0.044 Uiso 1 1 calc R U . . .
C10 C 0.2638(2) -0.0442(2) -0.1736(2) 0.0435(4) Uani 1 1 d . . . . .
H10A H 0.2215 -0.0881 -0.2881 0.052 Uiso 1 1 calc R U . . .
C11 C 0.2300(2) -0.13250(19) -0.1086(2) 0.0431(4) Uani 1 1 d . . . . .
H11A H 0.1621 -0.2383 -0.1778 0.052 Uiso 1 1 calc R U . . .
C12 C 0.2964(2) -0.06485(18) 0.0598(2) 0.0382(3) Uani 1 1 d . . . . .
H12A H 0.2739 -0.1271 0.1040 0.046 Uiso 1 1 calc R U . . .
C13 C 0.7922(2) 0.66557(19) 0.2917(2) 0.0401(3) Uani 1 1 d . . . . .
H13A H 0.7701 0.6436 0.1815 0.048 Uiso 1 1 calc R U . . .
H13B H 0.8548 0.7768 0.3653 0.048 Uiso 1 1 calc R U . . .
C14 C 0.8962(3) 0.5899(2) 0.3579(3) 0.0547(5) Uani 1 1 d . . . . .
H14A H 0.9969 0.6274 0.3639 0.082 Uiso 1 1 calc R U . . .
H14B H 0.9222 0.6133 0.4686 0.082 Uiso 1 1 calc R U . . .
H14C H 0.8372 0.4798 0.2844 0.082 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
I1 Na1 3.1373(7) . ?
I1 Na1 3.1775(6) 2_656 ?
S1 N008 1.6522(14) . ?
S1 N007 1.6693(13) . ?
S1 C13 1.7986(17) . ?
Na1 N3 2.4453(14) . ?
Na1 N1 2.4508(13) . ?
Na1 N2 2.4828(15) . ?
Na1 N008 2.9213(16) 2_666 ?
Na1 I1 3.1775(6) 2_656 ?
N1 C1 1.3409(18) . ?
N1 C2 1.3550(18) . ?
N2 C7 1.337(2) . ?
N2 C3 1.341(2) . ?
N3 C12 1.3342(19) . ?
N3 C8 1.3374(18) . ?
N007 C2 1.3117(18) . ?
N008 C1 1.3168(19) . ?
N008 Na1 2.9213(16) 2_666 ?
C1 C3 1.4992(19) . ?
C2 C8 1.5014(19) . ?
C3 C4 1.392(2) . ?
C4 C5 1.386(2) . ?
C5 C6 1.373(3) . ?
C6 C7 1.382(3) . ?
C8 C9 1.387(2) . ?
C9 C10 1.389(2) . ?
C10 C11 1.372(3) . ?
C11 C12 1.386(2) . ?
C13 C14 1.503(3) . ?

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
Na1 I1 Na1 85.589(16) . 2_656 ?
N008 S1 N007 108.54(7) . . ?
N008 S1 C13 103.52(8) . . ?
N007 S1 C13 103.37(8) . . ?
N3 Na1 N1 66.47(4) . . ?
N3 Na1 N2 133.06(5) . . ?
N1 Na1 N2 66.64(4) . . ?
N3 Na1 N008 105.48(5) . 2_666 ?
N1 Na1 N008 84.42(4) . 2_666 ?
N2 Na1 N008 72.05(4) . 2_666 ?
N3 Na1 I1 104.15(4) . . ?
N1 Na1 I1 116.04(4) . . ?
N2 Na1 I1 94.02(4) . . ?
N008 Na1 I1 148.99(3) 2_666 . ?
N3 Na1 I1 94.96(3) . 2_656 ?
N1 Na1 I1 146.92(4) . 2_656 ?
N2 Na1 I1 126.78(4) . 2_656 ?
N008 Na1 I1 74.18(3) 2_666 2_656 ?
I1 Na1 I1 94.410(16) . 2_656 ?
C1 N1 C2 117.47(12) . . ?
C1 N1 Na1 117.11(9) . . ?
C2 N1 Na1 119.81(9) . . ?
C7 N2 C3 117.13(14) . . ?
C7 N2 Na1 125.29(12) . . ?
C3 N2 Na1 116.94(10) . . ?
C12 N3 C8 117.44(13) . . ?
C12 N3 Na1 121.70(11) . . ?
C8 N3 Na1 120.69(10) . . ?
C2 N007 S1 115.98(11) . . ?
C1 N008 S1 116.05(11) . . ?
C1 N008 Na1 121.35(10) . 2_666 ?
S1 N008 Na1 104.86(6) . 2_666 ?
N008 C1 N1 129.35(13) . . ?
N008 C1 C3 114.25(13) . . ?
N1 C1 C3 116.34(12) . . ?
N007 C2 N1 129.72(13) . . ?
N007 C2 C8 115.01(12) . . ?
N1 C2 C8 115.22(12) . . ?
N2 C3 C4 123.04(14) . . ?
N2 C3 C1 117.09(13) . . ?
C4 C3 C1 119.85(14) . . ?
C5 C4 C3 118.42(16) . . ?
C6 C5 C4 119.00(16) . . ?
C5 C6 C7 118.72(16) . . ?
N2 C7 C6 123.67(17) . . ?
N3 C8 C9 123.14(14) . . ?
N3 C8 C2 115.98(12) . . ?
C9 C8 C2 120.86(13) . . ?
C8 C9 C10 118.52(15) . . ?
C11 C10 C9 118.68(15) . . ?
C10 C11 C12 118.98(15) . . ?
N3 C12 C11 123.21(15) . . ?
C14 C13 S1 115.40(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
N008 S1 N007 C2 -10.43(14) . . . . ?
C13 S1 N007 C2 99.04(13) . . . . ?
N007 S1 N008 C1 18.25(14) . . . . ?
C13 S1 N008 C1 -91.11(13) . . . . ?
N007 S1 N008 Na1 -118.53(6) . . . 2_666 ?
C13 S1 N008 Na1 132.11(7) . . . 2_666 ?
S1 N008 C1 N1 -15.2(2) . . . . ?
Na1 N008 C1 N1 113.98(15) 2_666 . . . ?
S1 N008 C1 C3 167.73(10) . . . . ?
Na1 N008 C1 C3 -63.07(15) 2_666 . . . ?
C2 N1 C1 N008 1.0(2) . . . . ?
Na1 N1 C1 N008 -152.62(13) . . . . ?
C2 N1 C1 C3 177.98(12) . . . . ?
Na1 N1 C1 C3 24.38(16) . . . . ?
S1 N007 C2 N1 -2.9(2) . . . . ?
S1 N007 C2 C8 174.35(10) . . . . ?
C1 N1 C2 N007 9.6(2) . . . . ?
Na1 N1 C2 N007 162.47(13) . . . . ?
C1 N1 C2 C8 -167.65(12) . . . . ?
Na1 N1 C2 C8 -14.78(16) . . . . ?
C7 N2 C3 C4 -1.0(2) . . . . ?
Na1 N2 C3 C4 170.25(11) . . . . ?
C7 N2 C3 C1 177.33(13) . . . . ?
Na1 N2 C3 C1 -11.40(16) . . . . ?
N008 C1 C3 N2 169.01(14) . . . . ?
N1 C1 C3 N2 -8.45(19) . . . . ?
N008 C1 C3 C4 -12.6(2) . . . . ?
N1 C1 C3 C4 169.95(13) . . . . ?
N2 C3 C4 C5 0.3(2) . . . . ?
C1 C3 C4 C5 -177.96(14) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C4 C5 C6 C7 -1.6(2) . . . . ?
C3 N2 C7 C6 0.3(2) . . . . ?
Na1 N2 C7 C6 -170.12(13) . . . . ?
C5 C6 C7 N2 1.0(3) . . . . ?
C12 N3 C8 C9 -1.9(2) . . . . ?
Na1 N3 C8 C9 173.51(12) . . . . ?
C12 N3 C8 C2 176.34(13) . . . . ?
Na1 N3 C8 C2 -8.24(16) . . . . ?
N007 C2 C8 N3 -162.74(13) . . . . ?
N1 C2 C8 N3 14.93(18) . . . . ?
N007 C2 C8 C9 15.6(2) . . . . ?
N1 C2 C8 C9 -166.77(14) . . . . ?
N3 C8 C9 C10 1.7(2) . . . . ?
C2 C8 C9 C10 -176.44(15) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C8 N3 C12 C11 0.5(2) . . . . ?
Na1 N3 C12 C11 -174.90(14) . . . . ?
C10 C11 C12 N3 1.1(3) . . . . ?
N008 S1 C13 C14 54.27(17) . . . . ?
N007 S1 C13 C14 -58.89(16) . . . . ?

_refine_diff_density_max         0.722
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_jb040
_database_code_depnum_ccdc_archive 'CCDC 1427398'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2016-01-19 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            'C14 H14 B F4 N5 S'
_chemical_formula_weight         371.17

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   9.9995(2)
_cell_length_b                   10.0313(2)
_cell_length_c                   16.1233(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1617.30(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9128
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.250
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6793
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(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            14055
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.397
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3960
_reflns_number_gt                3760
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.989

_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_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)+(0.0834P)²+0.1990P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1526 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.02(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3960
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.88601(6) 0.88699(7) 0.85223(4) 0.03477(19) Uani 1 1 d . . . . .
B1 B 0.2326(4) 0.5632(4) 0.8795(2) 0.0430(7) Uani 1 1 d . . . . .
F1 F 0.3197(2) 0.4566(2) 0.87057(14) 0.0591(6) Uani 1 1 d . . . . .
F2 F 0.3032(3) 0.6820(3) 0.87312(15) 0.0645(6) Uani 1 1 d . . . . .
F3 F 0.1744(3) 0.5587(3) 0.95635(19) 0.0901(11) Uani 1 1 d . . . . .
F4 F 0.1427(3) 0.5600(3) 0.8149(2) 0.0816(9) Uani 1 1 d . . . . .
N1 N 0.9032(2) 0.7385(3) 0.70080(16) 0.0377(5) Uani 1 1 d . . . . .
H1A H 0.9076 0.6951 0.6534 0.050(11) Uiso 1 1 calc R . . . .
N2 N 0.7642(2) 0.7908(3) 0.81381(15) 0.0370(5) Uani 1 1 d . . . . .
N3 N 1.0211(2) 0.8778(3) 0.79234(14) 0.0348(5) Uani 1 1 d . . . . .
N4 N 0.7149(2) 0.5984(3) 0.63117(15) 0.0345(5) Uani 1 1 d . . . . .
N5 N 1.1045(2) 0.7320(2) 0.59768(14) 0.0335(5) Uani 1 1 d . . . . .
C1 C 0.7871(2) 0.7327(3) 0.74406(16) 0.0311(5) Uani 1 1 d . . . . .
C2 C 1.0134(3) 0.8071(3) 0.72599(16) 0.0308(5) Uani 1 1 d . . . . .
C3 C 0.6806(2) 0.6508(3) 0.70410(15) 0.0288(5) Uani 1 1 d . . . . .
C4 C 0.5576(3) 0.6319(3) 0.74171(17) 0.0357(6) Uani 1 1 d . . . . .
H4A H 0.5370 0.6726 0.7933 0.043 Uiso 1 1 calc R U . . .
C5 C 0.4657(3) 0.5513(4) 0.7014(2) 0.0434(7) Uani 1 1 d . . . . .
H5A H 0.3805 0.5350 0.7254 0.052 Uiso 1 1 calc R U . . .
C6 C 0.4988(3) 0.4953(3) 0.6264(2) 0.0434(7) Uani 1 1 d . . . . .
H6A H 0.4375 0.4393 0.5980 0.052 Uiso 1 1 calc R U . . .
C7 C 0.6252(3) 0.5228(3) 0.59291(18) 0.0406(6) Uani 1 1 d . . . . .
H7A H 0.6475 0.4858 0.5405 0.049 Uiso 1 1 calc R U . . .
C8 C 1.1289(3) 0.7982(3) 0.66853(15) 0.0289(5) Uani 1 1 d . . . . .
C9 C 1.2493(3) 0.8567(3) 0.68842(17) 0.0359(6) Uani 1 1 d . . . . .
H9A H 1.2617 0.9008 0.7400 0.043 Uiso 1 1 calc R U . . .
C10 C 1.3522(3) 0.8491(3) 0.63061(18) 0.0404(6) Uani 1 1 d . . . . .
H10A H 1.4366 0.8889 0.6415 0.048 Uiso 1 1 calc R U . . .
C11 C 1.3289(3) 0.7821(3) 0.55677(19) 0.0405(6) Uani 1 1 d . . . . .
H11A H 1.3971 0.7756 0.5159 0.049 Uiso 1 1 calc R U . . .
C12 C 1.2047(3) 0.7248(3) 0.54344(17) 0.0369(6) Uani 1 1 d . . . . .
H12A H 1.1902 0.6779 0.4930 0.044 Uiso 1 1 calc R U . . .
C13 C 0.9385(3) 0.7887(3) 0.93953(17) 0.0393(6) Uani 1 1 d . . . . .
H13A H 0.8613 0.7715 0.9765 0.047 Uiso 1 1 calc R U . . .
H13B H 0.9737 0.7018 0.9202 0.047 Uiso 1 1 calc R U . . .
C14 C 1.0463(4) 0.8635(5) 0.9864(2) 0.0531(8) Uani 1 1 d . . . . .
H14A H 1.0753 0.8103 1.0342 0.080 Uiso 1 1 calc R U . . .
H14B H 1.1226 0.8795 0.9497 0.080 Uiso 1 1 calc R U . . .
H14C H 1.0106 0.9489 1.0058 0.080 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
S1 N3 1.663(2) . ?
S1 N2 1.673(3) . ?
S1 C13 1.797(3) . ?
B1 F3 1.369(4) . ?
B1 F4 1.377(5) . ?
B1 F1 1.387(4) . ?
B1 F2 1.388(5) . ?
N1 C1 1.355(3) . ?
N1 C2 1.362(4) . ?
N2 C1 1.287(4) . ?
N3 C2 1.286(3) . ?
N4 C7 1.327(4) . ?
N4 C3 1.333(3) . ?
N5 C12 1.332(4) . ?
N5 C8 1.343(3) . ?
C1 C3 1.492(4) . ?
C2 C8 1.483(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.387(4) . ?
C5 C6 1.373(5) . ?
C6 C7 1.402(4) . ?
C8 C9 1.378(4) . ?
C9 C10 1.390(4) . ?
C10 C11 1.387(4) . ?
C11 C12 1.386(4) . ?
C13 C14 1.516(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
N3 S1 N2 110.14(12) . . ?
N3 S1 C13 100.81(13) . . ?
N2 S1 C13 100.70(15) . . ?
F3 B1 F4 114.0(3) . . ?
F3 B1 F1 109.6(3) . . ?
F4 B1 F1 108.2(3) . . ?
F3 B1 F2 108.2(3) . . ?
F4 B1 F2 107.2(3) . . ?
F1 B1 F2 109.5(3) . . ?
C1 N1 C2 124.2(2) . . ?
C1 N2 S1 117.08(19) . . ?
C2 N3 S1 117.7(2) . . ?
C7 N4 C3 117.4(2) . . ?
C12 N5 C8 116.7(2) . . ?
N2 C1 N1 125.6(2) . . ?
N2 C1 C3 120.0(2) . . ?
N1 C1 C3 114.4(2) . . ?
N3 C2 N1 125.1(2) . . ?
N3 C2 C8 120.5(2) . . ?
N1 C2 C8 114.4(2) . . ?
N4 C3 C4 124.2(2) . . ?
N4 C3 C1 114.4(2) . . ?
C4 C3 C1 121.4(2) . . ?
C3 C4 C5 117.6(3) . . ?
C6 C5 C4 119.4(3) . . ?
C5 C6 C7 118.4(3) . . ?
N4 C7 C6 122.9(3) . . ?
N5 C8 C9 124.5(2) . . ?
N5 C8 C2 114.8(2) . . ?
C9 C8 C2 120.6(2) . . ?
C8 C9 C10 117.9(3) . . ?
C11 C10 C9 118.6(3) . . ?
C12 C11 C10 119.0(3) . . ?
N5 C12 C11 123.4(3) . . ?
C14 C13 S1 109.1(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
N3 S1 N2 C1 -4.2(3) . . . . ?
C13 S1 N2 C1 -110.0(2) . . . . ?
N2 S1 N3 C2 3.0(3) . . . . ?
C13 S1 N3 C2 108.7(3) . . . . ?
S1 N2 C1 N1 2.8(4) . . . . ?
S1 N2 C1 C3 -177.0(2) . . . . ?
C2 N1 C1 N2 0.4(5) . . . . ?
C2 N1 C1 C3 -179.8(3) . . . . ?
S1 N3 C2 N1 -0.2(4) . . . . ?
S1 N3 C2 C8 178.1(2) . . . . ?
C1 N1 C2 N3 -2.0(5) . . . . ?
C1 N1 C2 C8 179.7(3) . . . . ?
C7 N4 C3 C4 -0.4(4) . . . . ?
C7 N4 C3 C1 179.1(3) . . . . ?
N2 C1 C3 N4 178.4(3) . . . . ?
N1 C1 C3 N4 -1.4(3) . . . . ?
N2 C1 C3 C4 -2.1(4) . . . . ?
N1 C1 C3 C4 178.1(3) . . . . ?
N4 C3 C4 C5 1.2(4) . . . . ?
C1 C3 C4 C5 -178.2(3) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
C3 N4 C7 C6 -0.9(5) . . . . ?
C5 C6 C7 N4 1.3(5) . . . . ?
C12 N5 C8 C9 -0.7(4) . . . . ?
C12 N5 C8 C2 178.3(3) . . . . ?
N3 C2 C8 N5 -173.9(3) . . . . ?
N1 C2 C8 N5 4.6(4) . . . . ?
N3 C2 C8 C9 5.1(4) . . . . ?
N1 C2 C8 C9 -176.4(3) . . . . ?
N5 C8 C9 C10 1.3(4) . . . . ?
C2 C8 C9 C10 -177.6(3) . . . . ?
C8 C9 C10 C11 -0.7(5) . . . . ?
C9 C10 C11 C12 -0.3(5) . . . . ?
C8 N5 C12 C11 -0.5(4) . . . . ?
C10 C11 C12 N5 1.0(5) . . . . ?
N3 S1 C13 C14 69.7(2) . . . . ?
N2 S1 C13 C14 -177.2(2) . . . . ?

_refine_diff_density_max         0.883
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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 1427399'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-01-19 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            'C17 H17 F6 N5 O6 S3'
_chemical_formula_weight         597.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   8.938(4)
_cell_length_b                   11.927(5)
_cell_length_c                   12.900(5)
_cell_angle_alpha                96.902(19)
_cell_angle_beta                 108.004(18)
_cell_angle_gamma                107.987(17)
_cell_volume                     1208.1(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      33.13

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.746
_exptl_crystal_size_mid          0.448
_exptl_crystal_size_min          0.156
_exptl_absorpt_coefficient_mu    0.398
_shelx_estimated_absorpt_T_min   0.756
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_process_details   
;
Sheldrick G.M. (2008). SADABS-2008/1, Bruker/Siemens 
Area Detector Absorption Correction Program.
Bruker AXS, Madison, Wisconsin, USA.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'omega amd phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25311
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.198
_diffrn_reflns_theta_max         34.352
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9183
_reflns_number_gt                6831
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 One of triflate anions was modeled as disordered over three 
 positions with 0.435(1):0.435(1):0.131(2) occupancy ratio. 

 Restraints (SADI and SAME), mainly for S-C-F angle (S-F distance), 
 C-F distance, and S-C distance were applied to make the molecule 
 symmetrical and set its geometry equal for all three positions.

  Enhanced  rigid-bond restraints (RIGU) were also introduced for 
 atom ADPs. Constraints (EADP) for sulphur and oxygen atoms were 
 applied, equalizing ADPs for the first two positions.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0754P)²+0.3525P] 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         9183
_refine_ls_number_parameters     458
_refine_ls_number_restraints     261
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1422
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.002
_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 0.2459(2) -0.01800(15) 0.09978(16) 0.0402(3) Uani 1 1 d . . . . .
H1A H 0.1381 -0.0395 0.0374 0.060 Uiso 1 1 calc R U . . .
H1B H 0.3236 0.0614 0.1013 0.060 Uiso 1 1 calc R U . . .
H1C H 0.2267 -0.0145 0.1707 0.060 Uiso 1 1 calc R U . . .
N2 N 0.32071(15) -0.11099(11) 0.08459(11) 0.0306(2) Uani 1 1 d . . . . .
C3 C 0.2133(2) -0.22251(14) 0.02327(15) 0.0399(3) Uani 1 1 d . . . . .
H3 H 0.0949 -0.2405 -0.0010 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2722(2) -0.31121(15) -0.00492(16) 0.0441(4) Uani 1 1 d . . . . .
H4 H 0.1950 -0.3903 -0.0466 0.053 Uiso 1 1 calc R U . . .
C5 C 0.4439(2) -0.28431(15) 0.02783(16) 0.0443(4) Uani 1 1 d . . . . .
H5 H 0.4859 -0.3439 0.0067 0.053 Uiso 1 1 calc R U . . .
C6 C 0.5548(2) -0.16953(15) 0.09187(14) 0.0380(3) Uani 1 1 d . . . . .
H6 H 0.6735 -0.1498 0.1152 0.046 Uiso 1 1 calc R U . . .
C7 C 0.49063(18) -0.08381(13) 0.12146(12) 0.0295(3) Uani 1 1 d . . . . .
C8 C 0.60902(17) 0.03618(13) 0.19943(12) 0.0292(3) Uani 1 1 d . . . . .
N10 N 0.73109(16) 0.09430(12) 0.16652(11) 0.0349(3) Uani 1 1 d . . . . .
S11 S 0.88251(4) 0.21269(3) 0.26690(3) 0.03349(9) Uani 1 1 d . . . . .
N12 N 0.79510(16) 0.26279(12) 0.35068(12) 0.0342(3) Uani 1 1 d . . . . .
C13 C 0.66007(17) 0.18155(12) 0.35314(12) 0.0280(2) Uani 1 1 d . . . . .
C14 C 0.58220(16) 0.21509(12) 0.43398(12) 0.0279(2) Uani 1 1 d . . . . .
C15 C 0.46462(18) 0.12303(13) 0.45465(13) 0.0322(3) Uani 1 1 d . . . . .
H15 H 0.4292 0.0419 0.4134 0.039 Uiso 1 1 calc R U . . .
C16 C 0.3975(2) 0.14706(15) 0.53450(14) 0.0381(3) Uani 1 1 d . . . . .
H16 H 0.3169 0.0831 0.5481 0.046 Uiso 1 1 calc R U . . .
C17 C 0.4492(2) 0.26490(17) 0.59398(15) 0.0439(4) Uani 1 1 d . . . . .
H17 H 0.4082 0.2834 0.6510 0.053 Uiso 1 1 calc R U . . .
C18 C 0.5614(2) 0.35488(16) 0.56877(15) 0.0414(4) Uani 1 1 d . . . . .
H18 H 0.5947 0.4366 0.6077 0.050 Uiso 1 1 calc R U . . .
N19 N 0.62620(15) 0.33140(11) 0.49050(11) 0.0322(2) Uani 1 1 d . . . . .
C20 C 0.7333(2) 0.43903(14) 0.46559(16) 0.0437(4) Uani 1 1 d . . . . .
H20A H 0.7279 0.5127 0.5044 0.066 Uiso 1 1 calc R U . . .
H20B H 0.6922 0.4325 0.3845 0.066 Uiso 1 1 calc R U . . .
H20C H 0.8505 0.4431 0.4914 0.066 Uiso 1 1 calc R U . . .
C21 C 1.0032(2) 0.14218(17) 0.35577(16) 0.0431(4) Uani 1 1 d . . . . .
H21A H 0.9289 0.0821 0.3813 0.065 Uiso 1 1 calc R U . . .
H21B H 1.0925 0.2041 0.4209 0.065 Uiso 1 1 calc R U . . .
H21C H 1.0543 0.1018 0.3137 0.065 Uiso 1 1 calc R U . . .
N22 N 0.57421(15) 0.06597(11) 0.29012(10) 0.0307(2) Uani 1 1 d . . . . .
S30 S 0.29078(4) 0.30293(3) 0.20835(3) 0.03225(9) Uani 1 1 d . . . . .
O31 O 0.43885(15) 0.28338(12) 0.20006(12) 0.0465(3) Uani 1 1 d . . . . .
O32 O 0.13197(15) 0.20560(11) 0.14446(11) 0.0422(3) Uani 1 1 d . . . . .
O33 O 0.30945(17) 0.35548(11) 0.32102(10) 0.0435(3) Uani 1 1 d . . . . .
C30 C 0.2792(2) 0.42454(16) 0.13577(15) 0.0424(4) Uani 1 1 d . . . . .
F31 F 0.41888(18) 0.52183(12) 0.18421(12) 0.0679(4) Uani 1 1 d . . . . .
F32 F 0.2595(2) 0.39282(14) 0.02917(11) 0.0776(4) Uani 1 1 d . . . . .
F33 F 0.15113(18) 0.45709(13) 0.13802(14) 0.0728(4) Uani 1 1 d . . . . .
S40 S 0.9897(17) 0.8226(7) 0.3059(11) 0.0403(4) Uani 0.4346(10) 1 d D U P A 1
O41 O 1.1479(13) 0.8606(14) 0.4112(11) 0.075(2) Uani 0.4346(10) 1 d D U P A 1
O42 O 0.976(4) 0.841(2) 0.1949(15) 0.069(2) Uani 0.4346(10) 1 d D U P A 1
O43 O 0.852(3) 0.839(3) 0.336(2) 0.077(3) Uani 0.4346(10) 1 d D U P A 1
C40 C 0.9307(14) 0.6607(9) 0.2858(9) 0.058(2) Uani 0.4346(10) 1 d D U P A 1
F41 F 1.0433(13) 0.6198(8) 0.2688(8) 0.106(2) Uani 0.4346(10) 1 d D U P A 1
F42 F 0.7905(14) 0.6019(13) 0.1934(10) 0.086(3) Uani 0.4346(10) 1 d D U P A 1
F43 F 0.9167(11) 0.6249(7) 0.3764(7) 0.0805(18) Uani 0.4346(10) 1 d D U P A 1
S40' S 0.9958(17) 0.8205(7) 0.3121(11) 0.0403(4) Uani 0.4346(10) 1 d D U P A 2
O41' O 1.1651(12) 0.8617(12) 0.3726(7) 0.075(2) Uani 0.4346(10) 1 d . U P A 2
O42' O 0.974(4) 0.862(2) 0.2105(15) 0.069(2) Uani 0.4346(10) 1 d . U P A 2
O43' O 0.879(3) 0.836(3) 0.358(2) 0.077(3) Uani 0.4346(10) 1 d . U P A 2
C40' C 0.9389(14) 0.6580(9) 0.2693(9) 0.063(2) Uani 0.4346(10) 1 d D U P A 2
F41' F 1.0158(13) 0.6255(8) 0.2076(7) 0.108(2) Uani 0.4346(10) 1 d D U P A 2
F42' F 0.7661(12) 0.6040(11) 0.2118(10) 0.075(2) Uani 0.4346(10) 1 d D U P A 2
F43' F 0.9739(12) 0.6108(8) 0.3565(8) 0.120(3) Uani 0.4346(10) 1 d D U P A 2
S40" S 0.9734(5) 0.7767(4) 0.3536(4) 0.0521(13) Uani 0.131(2) 1 d D U P A 3
O41" O 1.1579(18) 0.8742(15) 0.4065(17) 0.038(3) Uani 0.131(2) 1 d D U P A 3
O42" O 0.917(2) 0.6929(15) 0.4158(13) 0.074(4) Uani 0.131(2) 1 d D U P A 3
O43" O 0.8585(17) 0.8393(12) 0.3125(19) 0.069(5) Uani 0.131(2) 1 d D U P A 3
C40" C 0.983(2) 0.6976(15) 0.2333(13) 0.102(5) Uani 0.131(2) 1 d D U P A 3
F41" F 0.994(3) 0.767(2) 0.1598(13) 0.145(6) Uani 0.131(2) 1 d D U P A 3
F42" F 1.120(2) 0.6701(19) 0.2538(19) 0.117(6) Uani 0.131(2) 1 d D U P A 3
F43" F 0.852(3) 0.5958(15) 0.1796(15) 0.099(6) Uani 0.131(2) 1 d D U P A 3


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.484(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 C3 1.344(2) . ?
N2 C7 1.3603(19) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.497(2) . ?
C8 N10 1.3194(19) . ?
C8 N22 1.3361(18) . ?
N10 S11 1.6731(15) . ?
S11 N12 1.6703(14) . ?
S11 C21 1.7925(18) . ?
N12 C13 1.3059(19) . ?
C13 N22 1.3571(19) . ?
C13 C14 1.5008(19) . ?
C14 N19 1.3614(19) . ?
C14 C15 1.383(2) . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.372(3) . ?
C17 H17 0.9500 . ?
C18 N19 1.352(2) . ?
C18 H18 0.9500 . ?
N19 C20 1.482(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
S30 O32 1.4390(13) . ?
S30 O31 1.4455(13) . ?
S30 O33 1.4490(13) . ?
S30 C30 1.8305(19) . ?
C30 F31 1.321(2) . ?
C30 F32 1.323(2) . ?
C30 F33 1.324(2) . ?
S40 O42 1.447(17) . ?
S40 O43 1.465(17) . ?
S40 O41 1.523(14) . ?
S40 C40 1.800(9) . ?
C40 F41 1.308(9) . ?
C40 F43 1.319(9) . ?
C40 F42 1.347(10) . ?
S40' O41' 1.364(16) . ?
S40' O43' 1.401(19) . ?
S40' O42' 1.437(18) . ?
S40' C40' 1.811(9) . ?
C40' F43' 1.313(9) . ?
C40' F41' 1.298(10) . ?
C40' F42' 1.383(10) . ?
S40" O42" 1.425(14) . ?
S40" O43" 1.458(12) . ?
S40" O41" 1.570(14) . ?
S40" C40" 1.755(14) . ?
C40" F43" 1.318(13) . ?
C40" F42" 1.324(13) . ?
C40" F41" 1.342(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 N2 C7 120.45(13) . . ?
C3 N2 C1 116.92(13) . . ?
C7 N2 C1 122.35(13) . . ?
N2 C3 C4 121.02(16) . . ?
N2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 119.51(16) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 119.48(16) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 119.29(16) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N2 C7 C6 120.17(14) . . ?
N2 C7 C8 120.19(12) . . ?
C6 C7 C8 119.55(13) . . ?
N10 C8 N22 131.04(14) . . ?
N10 C8 C7 113.89(13) . . ?
N22 C8 C7 115.06(12) . . ?
C8 N10 S11 112.52(11) . . ?
N12 S11 N10 107.94(7) . . ?
N12 S11 C21 100.88(8) . . ?
N10 S11 C21 102.77(9) . . ?
C13 N12 S11 114.99(11) . . ?
N12 C13 N22 128.68(13) . . ?
N12 C13 C14 118.73(13) . . ?
N22 C13 C14 112.58(12) . . ?
N19 C14 C15 118.64(13) . . ?
N19 C14 C13 122.98(12) . . ?
C15 C14 C13 118.34(12) . . ?
C14 C15 C16 121.13(14) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 119.17(15) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C18 C17 C16 118.37(15) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
N19 C18 C17 122.38(15) . . ?
N19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C18 N19 C14 120.21(13) . . ?
C18 N19 C20 115.85(13) . . ?
C14 N19 C20 123.76(13) . . ?
N19 C20 H20A 109.5 . . ?
N19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
S11 C21 H21A 109.5 . . ?
S11 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S11 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C8 N22 C13 116.97(12) . . ?
O32 S30 O31 115.50(8) . . ?
O32 S30 O33 115.05(8) . . ?
O31 S30 O33 114.40(8) . . ?
O32 S30 C30 102.96(9) . . ?
O31 S30 C30 103.18(9) . . ?
O33 S30 C30 103.33(8) . . ?
F31 C30 F32 107.47(17) . . ?
F31 C30 F33 107.41(16) . . ?
F32 C30 F33 107.18(17) . . ?
F31 C30 S30 110.57(13) . . ?
F32 C30 S30 112.48(13) . . ?
F33 C30 S30 111.48(13) . . ?
O42 S40 O43 111.9(16) . . ?
O42 S40 O41 128.7(16) . . ?
O43 S40 O41 109.3(13) . . ?
O42 S40 C40 103.1(11) . . ?
O43 S40 C40 100.4(15) . . ?
O41 S40 C40 98.2(9) . . ?
F41 C40 F43 102.6(8) . . ?
F41 C40 F42 104.2(10) . . ?
F43 C40 F42 112.6(11) . . ?
F41 C40 S40 114.2(8) . . ?
F43 C40 S40 111.8(7) . . ?
F42 C40 S40 111.0(8) . . ?
O41' S40' O43' 122.7(14) . . ?
O41' S40' O42' 107.3(15) . . ?
O43' S40' O42' 110.5(16) . . ?
O41' S40' C40' 103.5(9) . . ?
O43' S40' C40' 105.9(15) . . ?
O42' S40' C40' 105.5(11) . . ?
F43' C40' F41' 106.0(9) . . ?
F43' C40' F42' 106.5(10) . . ?
F41' C40' F42' 109.2(10) . . ?
F43' C40' S40' 111.3(8) . . ?
F41' C40' S40' 114.4(8) . . ?
F42' C40' S40' 109.2(7) . . ?
O42" S40" O43" 113.1(10) . . ?
O42" S40" O41" 119.2(10) . . ?
O43" S40" O41" 107.8(9) . . ?
O42" S40" C40" 109.3(10) . . ?
O43" S40" C40" 105.5(11) . . ?
O41" S40" C40" 100.5(9) . . ?
F43" C40" F42" 106.7(17) . . ?
F43" C40" F41" 107.2(17) . . ?
F42" C40" F41" 103.6(17) . . ?
F43" C40" S40" 114.8(12) . . ?
F42" C40" S40" 113.2(11) . . ?
F41" C40" S40" 110.5(11) . . ?

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
C7 N2 C3 C4 -0.8(2) . . . . ?
C1 N2 C3 C4 173.35(16) . . . . ?
N2 C3 C4 C5 -1.7(3) . . . . ?
C3 C4 C5 C6 2.1(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C3 N2 C7 C6 2.8(2) . . . . ?
C1 N2 C7 C6 -171.04(15) . . . . ?
C3 N2 C7 C8 -173.70(14) . . . . ?
C1 N2 C7 C8 12.4(2) . . . . ?
C5 C6 C7 N2 -2.3(2) . . . . ?
C5 C6 C7 C8 174.26(14) . . . . ?
N2 C7 C8 N10 -129.17(15) . . . . ?
C6 C7 C8 N10 54.28(19) . . . . ?
N2 C7 C8 N22 51.14(18) . . . . ?
C6 C7 C8 N22 -125.42(15) . . . . ?
N22 C8 N10 S11 11.5(2) . . . . ?
C7 C8 N10 S11 -168.12(10) . . . . ?
C8 N10 S11 N12 -27.54(13) . . . . ?
C8 N10 S11 C21 78.53(13) . . . . ?
N10 S11 N12 C13 25.64(14) . . . . ?
C21 S11 N12 C13 -81.75(13) . . . . ?
S11 N12 C13 N22 -6.2(2) . . . . ?
S11 N12 C13 C14 174.43(10) . . . . ?
N12 C13 C14 N19 12.1(2) . . . . ?
N22 C13 C14 N19 -167.38(13) . . . . ?
N12 C13 C14 C15 -165.63(14) . . . . ?
N22 C13 C14 C15 14.87(18) . . . . ?
N19 C14 C15 C16 -2.7(2) . . . . ?
C13 C14 C15 C16 175.14(14) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C15 C16 C17 C18 2.3(3) . . . . ?
C16 C17 C18 N19 -2.0(3) . . . . ?
C17 C18 N19 C14 -0.6(3) . . . . ?
C17 C18 N19 C20 174.61(18) . . . . ?
C15 C14 N19 C18 3.0(2) . . . . ?
C13 C14 N19 C18 -174.77(14) . . . . ?
C15 C14 N19 C20 -171.87(15) . . . . ?
C13 C14 N19 C20 10.4(2) . . . . ?
N10 C8 N22 C13 11.0(2) . . . . ?
C7 C8 N22 C13 -169.37(12) . . . . ?
N12 C13 N22 C8 -14.2(2) . . . . ?
C14 C13 N22 C8 165.22(12) . . . . ?
O32 S30 C30 F31 -179.29(13) . . . . ?
O31 S30 C30 F31 -58.79(15) . . . . ?
O33 S30 C30 F31 60.64(15) . . . . ?
O32 S30 C30 F32 -59.13(16) . . . . ?
O31 S30 C30 F32 61.37(16) . . . . ?
O33 S30 C30 F32 -179.20(14) . . . . ?
O32 S30 C30 F33 61.29(15) . . . . ?
O31 S30 C30 F33 -178.21(13) . . . . ?
O33 S30 C30 F33 -58.77(15) . . . . ?
O42 S40 C40 F41 71.4(15) . . . . ?
O43 S40 C40 F41 -173.0(13) . . . . ?
O41 S40 C40 F41 -61.6(12) . . . . ?
O42 S40 C40 F43 -172.7(14) . . . . ?
O43 S40 C40 F43 -57.1(14) . . . . ?
O41 S40 C40 F43 54.4(12) . . . . ?
O42 S40 C40 F42 -46.0(16) . . . . ?
O43 S40 C40 F42 69.5(14) . . . . ?
O41 S40 C40 F42 -179.0(11) . . . . ?
O41' S40' C40' F43' 59.4(12) . . . . ?
O43' S40' C40' F43' -70.9(14) . . . . ?
O42' S40' C40' F43' 171.9(15) . . . . ?
O41' S40' C40' F41' -60.7(11) . . . . ?
O43' S40' C40' F41' 169.0(13) . . . . ?
O42' S40' C40' F41' 51.8(16) . . . . ?
O41' S40' C40' F42' 176.6(10) . . . . ?
O43' S40' C40' F42' 46.4(14) . . . . ?
O42' S40' C40' F42' -70.8(16) . . . . ?
O42" S40" C40" F43" 43.2(17) . . . . ?
O43" S40" C40" F43" -78.7(16) . . . . ?
O41" S40" C40" F43" 169.4(16) . . . . ?
O42" S40" C40" F42" -79.7(17) . . . . ?
O43" S40" C40" F42" 158.4(15) . . . . ?
O41" S40" C40" F42" 46.4(17) . . . . ?
O42" S40" C40" F41" 164.6(15) . . . . ?
O43" S40" C40" F41" 42.7(16) . . . . ?
O41" S40" C40" F41" -69.2(16) . . . . ?

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
C1 H1B O31 0.98 2.53 3.353(3) 141.8 .
C1 H1C O42 0.98 2.50 3.16(2) 124.1 1_445
C1 H1C O42' 0.98 2.52 3.24(2) 129.5 1_445
C3 H3 O32 0.95 2.47 3.257(2) 140.3 2
C3 H3 F41" 0.95 2.51 2.999(16) 112.3 1_445
C6 H6 O42 0.95 2.62 3.54(3) 162.7 1_545
C6 H6 O42' 0.95 2.54 3.46(3) 164.3 1_545
C6 H6 O43" 0.95 2.61 3.233(16) 123.1 1_545
C15 H15 O41' 0.95 2.51 3.210(11) 130.6 1_445
C15 H15 O41" 0.95 2.59 3.192(15) 121.4 1_445
C17 H17 F31 0.95 2.62 3.219(3) 121.4 2_666
C17 H17 O43 0.95 2.40 3.05(2) 125.2 2_666
C17 H17 O43' 0.95 2.48 3.09(2) 122.0 2_666
C17 H17 O43" 0.95 2.60 3.296(19) 130.6 2_666
C18 H18 O33 0.95 2.32 3.260(3) 170.6 2_666
C20 H20C F43' 0.98 2.40 3.170(8) 135.2 2_766
C21 H21B O42" 0.98 2.35 3.082(18) 131.3 2_766


_refine_diff_density_max         0.638
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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 1440653'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-01-19 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            'C14 H13 N5 S'
_chemical_formula_weight         283.35

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   5.799(3)
_cell_length_b                   14.641(9)
_cell_length_c                   16.056(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1363.2(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    258(2)
_cell_measurement_reflns_used    4037
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      27.71

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.883
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   0.820
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6335
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      258(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            11126
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.882
_diffrn_reflns_theta_max         28.089
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3294
_reflns_number_gt                2548
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    1.000

_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.0557P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 874 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3294
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.0997
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
C2 C 0.1824(5) 0.52613(15) 0.53145(14) 0.0371(6) Uani 1 1 d . . . . .
C4 C 0.4897(5) 0.43815(15) 0.57719(14) 0.0378(6) Uani 1 1 d . . . . .
C6 C 0.1644(6) 0.32958(16) 0.44528(15) 0.0469(7) Uani 1 1 d . . . . .
H6A H 0.2471 0.2722 0.4500 0.056 Uiso 1 1 calc R U . . .
H6B H 0.0810 0.3396 0.4968 0.056 Uiso 1 1 calc R U . . .
C7 C -0.0035(6) 0.3246(2) 0.37363(18) 0.0616(9) Uani 1 1 d . . . . .
H7A H -0.0832 0.3818 0.3685 0.092 Uiso 1 1 calc R U . . .
H7B H -0.1130 0.2767 0.3837 0.092 Uiso 1 1 calc R U . . .
H7C H 0.0788 0.3121 0.3230 0.092 Uiso 1 1 calc R U . . .
C8 C -0.0022(5) 0.59200(15) 0.55722(15) 0.0392(6) Uani 1 1 d . . . . .
C9 C -0.0220(6) 0.61843(18) 0.63997(16) 0.0496(7) Uani 1 1 d . . . . .
H9 H 0.0829 0.5979 0.6796 0.060 Uiso 1 1 calc R U . . .
C10 C -0.1995(7) 0.6755(2) 0.66221(19) 0.0599(9) Uani 1 1 d . . . . .
H10 H -0.2161 0.6940 0.7173 0.072 Uiso 1 1 calc R U . . .
C11 C -0.3513(6) 0.70487(19) 0.60321(19) 0.0576(8) Uani 1 1 d . . . . .
H11 H -0.4725 0.7436 0.6171 0.069 Uiso 1 1 calc R U . . .
C12 C -0.3205(6) 0.67581(19) 0.52275(19) 0.0561(8) Uani 1 1 d . . . . .
H12 H -0.4236 0.6961 0.4825 0.067 Uiso 1 1 calc R U . . .
C14 C 0.6408(5) 0.41939(16) 0.65058(13) 0.0373(6) Uani 1 1 d . . . . .
C15 C 0.5723(5) 0.44532(17) 0.73047(15) 0.0459(7) Uani 1 1 d . . . . .
H15 H 0.4317 0.4746 0.7385 0.055 Uiso 1 1 calc R U . . .
C16 C 0.7140(6) 0.42733(19) 0.79722(16) 0.0531(8) Uani 1 1 d . . . . .
H16 H 0.6702 0.4436 0.8509 0.064 Uiso 1 1 calc R U . . .
C17 C 0.9221(6) 0.38482(19) 0.78283(16) 0.0552(8) Uani 1 1 d . . . . .
H17 H 1.0236 0.3725 0.8263 0.066 Uiso 1 1 calc R U . . .
C18 C 0.9752(6) 0.36097(18) 0.70175(16) 0.0515(7) Uani 1 1 d . . . . .
H18 H 1.1159 0.3323 0.6924 0.062 Uiso 1 1 calc R U . . .
N1 N 0.2086(4) 0.51272(14) 0.44986(12) 0.0433(6) Uani 1 1 d . . . . .
N3 N 0.3043(4) 0.49064(14) 0.59448(12) 0.0404(5) Uani 1 1 d . . . . .
N5 N 0.5549(4) 0.40338(15) 0.50539(12) 0.0450(6) Uani 1 1 d . . . . .
N13 N -0.1502(5) 0.61988(14) 0.49898(13) 0.0471(6) Uani 1 1 d . . . . .
N19 N 0.8403(4) 0.37593(14) 0.63613(12) 0.0431(5) Uani 1 1 d . . . . .
S1 S 0.36688(13) 0.42156(4) 0.42889(3) 0.0433(2) 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
C2 N1 1.333(3) . ?
C2 N3 1.339(3) . ?
C2 C8 1.499(4) . ?
C4 N5 1.316(3) . ?
C4 N3 1.351(3) . ?
C4 C14 1.494(3) . ?
C6 C7 1.509(4) . ?
C6 S1 1.806(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N13 1.333(3) . ?
C8 C9 1.389(3) . ?
C9 C10 1.373(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(4) . ?
C11 H11 0.9300 . ?
C12 N13 1.338(4) . ?
C12 H12 0.9300 . ?
C14 N19 1.341(4) . ?
C14 C15 1.395(3) . ?
C15 C16 1.376(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(3) . ?
C17 H17 0.9300 . ?
C18 N19 1.330(3) . ?
C18 H18 0.9300 . ?
N1 S1 1.654(2) . ?
N5 S1 1.664(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C2 N3 128.7(2) . . ?
N1 C2 C8 116.6(2) . . ?
N3 C2 C8 114.7(2) . . ?
N5 C4 N3 129.0(2) . . ?
N5 C4 C14 116.8(2) . . ?
N3 C4 C14 114.2(2) . . ?
C7 C6 S1 110.16(19) . . ?
C7 C6 H6A 109.6 . . ?
S1 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
S1 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N13 C8 C9 122.2(3) . . ?
N13 C8 C2 117.6(2) . . ?
C9 C8 C2 120.2(2) . . ?
C10 C9 C8 118.7(3) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 118.2(3) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
N13 C12 C11 123.7(3) . . ?
N13 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
N19 C14 C15 122.3(2) . . ?
N19 C14 C4 117.2(2) . . ?
C15 C14 C4 120.6(2) . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 118.6(2) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C16 C17 C18 117.9(3) . . ?
C16 C17 H17 121.1 . . ?
C18 C17 H17 121.1 . . ?
N19 C18 C17 125.0(3) . . ?
N19 C18 H18 117.5 . . ?
C17 C18 H18 117.5 . . ?
C2 N1 S1 112.45(17) . . ?
C2 N3 C4 119.1(2) . . ?
C4 N5 S1 113.36(19) . . ?
C8 N13 C12 117.5(2) . . ?
C18 N19 C14 116.6(2) . . ?
N1 S1 N5 110.02(11) . . ?
N1 S1 C6 102.20(14) . . ?
N5 S1 C6 101.49(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
N1 C2 C8 N13 11.1(3) . . . . ?
N3 C2 C8 N13 -170.8(2) . . . . ?
N1 C2 C8 C9 -172.0(3) . . . . ?
N3 C2 C8 C9 6.0(4) . . . . ?
N13 C8 C9 C10 -0.3(4) . . . . ?
C2 C8 C9 C10 -177.0(3) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C10 C11 C12 N13 0.3(5) . . . . ?
N5 C4 C14 N19 5.9(3) . . . . ?
N3 C4 C14 N19 -173.1(2) . . . . ?
N5 C4 C14 C15 -173.2(2) . . . . ?
N3 C4 C14 C15 7.8(3) . . . . ?
N19 C14 C15 C16 1.0(4) . . . . ?
C4 C14 C15 C16 180.0(2) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C15 C16 C17 C18 -1.2(4) . . . . ?
C16 C17 C18 N19 0.0(4) . . . . ?
N3 C2 N1 S1 16.7(4) . . . . ?
C8 C2 N1 S1 -165.56(18) . . . . ?
N1 C2 N3 C4 4.6(4) . . . . ?
C8 C2 N3 C4 -173.1(2) . . . . ?
N5 C4 N3 C2 -11.5(4) . . . . ?
C14 C4 N3 C2 167.3(2) . . . . ?
N3 C4 N5 S1 -5.3(4) . . . . ?
C14 C4 N5 S1 175.89(15) . . . . ?
C9 C8 N13 C12 0.6(4) . . . . ?
C2 C8 N13 C12 177.4(2) . . . . ?
C11 C12 N13 C8 -0.6(5) . . . . ?
C17 C18 N19 C14 1.6(4) . . . . ?
C15 C14 N19 C18 -2.1(4) . . . . ?
C4 C14 N19 C18 178.9(2) . . . . ?
C2 N1 S1 N5 -29.2(2) . . . . ?
C2 N1 S1 C6 78.0(2) . . . . ?
C4 N5 S1 N1 24.4(2) . . . . ?
C4 N5 S1 C6 -83.3(2) . . . . ?
C7 C6 S1 N1 75.1(2) . . . . ?
C7 C6 S1 N5 -171.28(19) . . . . ?

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
C6 H6A N19 0.97 2.63 3.435(4) 140.9 4_456
C6 H6B N19 0.97 2.69 3.658(4) 176.8 1_455
C6 H6A N19 0.97 2.63 3.435(4) 140.9 4_456
C6 H6B N19 0.97 2.69 3.658(4) 176.8 1_455

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.045

