# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_global
_database_code_depnum_ccdc_archive 'CCDC 1491087'
_audit_update_record             
;
2016-08-02 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;
_audit_creation_date             2016-05-31
_audit_creation_method           'by CrystalStructure 4.2'

#==============================================================================
#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H20 N O4 S'
_chemical_formula_moiety         'C20 H20 N O4 S'
_chemical_formula_weight         370.44
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_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                   5.51851(12)
_cell_length_b                   40.4605(8)
_cell_length_c                   8.28955(19)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.953(2)
_cell_angle_gamma                90.0000
_cell_volume                     1840.92(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5813
_cell_measurement_theta_min      4.44
_cell_measurement_theta_max      76.92
_cell_measurement_temperature    213
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             780.00
_exptl_absorpt_coefficient_mu    1.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.5a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_T_max  0.965

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      213
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            10722
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_theta_max         77.463
_diffrn_reflns_theta_min         5.476
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3747
_reflns_number_gt                3158
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1537
_refine_ls_wR_factor_gt          0.1478
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3747
_refine_ls_number_parameters     236
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0679P)²+1.0544P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.61558(10) 0.28682(2) 0.60129(8) 0.0475(2) Uani 1 1 d . . . . .
O1 O 0.4441(4) 0.26326(5) 0.6429(3) 0.0880(8) Uani 1 1 d . . . . .
O2 O 0.8602(4) 0.28044(5) 0.6616(5) 0.1232(13) Uani 1 1 d . . . . .
O3 O 0.5941(5) 0.29177(5) 0.4272(3) 0.0909(8) Uani 1 1 d . . . . .
O4 O 0.3784(6) 0.52744(6) 0.5517(3) 0.0910(8) Uani 1 1 d . . . . .
N1 N 1.0729(4) 0.22302(5) 0.7976(3) 0.0553(5) Uani 1 1 d . . . . .
H1A H 1.0463 0.2439 0.7624 0.066 Uiso 1 1 calc R U . . .
H1B H 1.2255 0.2213 0.8469 0.066 Uiso 1 1 calc R U . . .
H1C H 0.9657 0.2179 0.8684 0.066 Uiso 1 1 calc R U . . .
C1 C 0.5381(4) 0.32541(5) 0.6823(3) 0.0416(5) Uani 1 1 d . . . . .
C2 C 0.3398(4) 0.32810(6) 0.7705(3) 0.0494(5) Uani 1 1 d . . . . .
H2 H 0.2505 0.3091 0.7927 0.059 Uiso 1 1 calc R U . . .
C3 C 0.2726(5) 0.35860(6) 0.8261(3) 0.0514(6) Uani 1 1 d . . . . .
H3 H 0.1376 0.3603 0.8860 0.062 Uiso 1 1 calc R U . . .
C4 C 0.4037(4) 0.38687(6) 0.7939(3) 0.0458(5) Uani 1 1 d . . . . .
C5 C 0.6059(4) 0.38384(6) 0.7071(3) 0.0500(6) Uani 1 1 d . . . . .
H5 H 0.6973 0.4027 0.6863 0.060 Uiso 1 1 calc R U . . .
C6 C 0.6726(4) 0.35340(6) 0.6514(3) 0.0473(5) Uani 1 1 d . . . . .
H6 H 0.8087 0.3515 0.5926 0.057 Uiso 1 1 calc R U . . .
C7 C 0.3207(5) 0.41817(6) 0.8465(3) 0.0509(6) Uani 1 1 d . . . . .
C8 C 0.2339(5) 0.44334(6) 0.8899(3) 0.0511(6) Uani 1 1 d . . . . .
C9 C 0.1176(4) 0.47227(6) 0.9452(3) 0.0453(5) Uani 1 1 d . . . . .
C10 C -0.0903(4) 0.46881(6) 1.0259(3) 0.0490(5) Uani 1 1 d . . . . .
H10 H -0.1520 0.4476 1.0435 0.059 Uiso 1 1 calc R U . . .
C11 C 0.2057(4) 0.50387(6) 0.9200(3) 0.0491(5) Uani 1 1 d . . . . .
H11 H 0.3455 0.5066 0.8654 0.059 Uiso 1 1 calc R U . . .
C12 C 0.9989(5) 0.16508(6) 0.7103(3) 0.0514(6) Uani 1 1 d . . . . .
C13 C 0.7839(5) 0.14942(7) 0.6572(4) 0.0629(7) Uani 1 1 d . . . . .
H13 H 0.6655 0.1607 0.5883 0.076 Uiso 1 1 calc R U . . .
C14 C 0.7398(5) 0.11742(7) 0.7036(4) 0.0654(7) Uani 1 1 d . . . . .
H14 H 0.5929 0.1070 0.6653 0.079 Uiso 1 1 calc R U . . .
C15 C 0.9106(5) 0.10073(6) 0.8061(3) 0.0595(7) Uani 1 1 d . . . . .
H15 H 0.8795 0.0791 0.8397 0.071 Uiso 1 1 calc R U . . .
C16 C 1.1271(5) 0.11605(6) 0.8586(3) 0.0598(7) Uani 1 1 d . . . . .
H16 H 1.2457 0.1047 0.9272 0.072 Uiso 1 1 calc R U . . .
C17 C 1.1706(5) 0.14798(6) 0.8110(3) 0.0553(6) Uani 1 1 d . . . . .
H17 H 1.3191 0.1582 0.8475 0.066 Uiso 1 1 calc R U . . .
C18 C 1.0421(7) 0.20019(7) 0.6590(4) 0.0698(8) Uani 1 1 d . . . . .
H18A H 1.1883 0.2009 0.6014 0.084 Uiso 1 1 calc R U . . .
H18B H 0.9038 0.2075 0.5837 0.084 Uiso 1 1 calc R U . . .
C19 C 0.2985(6) 0.51114(11) 0.4075(4) 0.0872(11) Uani 1 1 d . . . . .
H19A H 0.3712 0.5215 0.3170 0.105 Uiso 1 1 calc R U . . .
H19B H 0.1210 0.5131 0.3864 0.105 Uiso 1 1 calc R U . . .
C20 C 0.6322(9) 0.52399(11) 0.5812(4) 0.0933(12) Uani 1 1 d . . . . .
H20A H 0.6900 0.5352 0.6827 0.112 Uiso 1 1 calc R U . . .
H20B H 0.7100 0.5345 0.4933 0.112 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O1 1.411(2) . ?
S1 O2 1.414(2) . ?
S1 O3 1.449(2) . ?
S1 C1 1.770(2) . ?
O4 C19 1.396(4) . ?
O4 C20 1.404(5) . ?
N1 C18 1.470(3) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N1 H1C 0.9000 . ?
C1 C2 1.382(3) . ?
C1 C6 1.392(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.394(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.394(3) . ?
C4 C7 1.430(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.197(3) . ?
C8 C9 1.433(3) . ?
C9 C11 1.391(3) . ?
C9 C10 1.394(3) . ?
C10 C11 1.374(3) 3_567 ?
C10 H10 0.9400 . ?
C11 C10 1.374(3) 3_567 ?
C11 H11 0.9400 . ?
C12 C13 1.377(4) . ?
C12 C17 1.382(4) . ?
C12 C18 1.509(4) . ?
C13 C14 1.380(4) . ?
C13 H13 0.9400 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9400 . ?
C15 C16 1.376(4) . ?
C15 H15 0.9400 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9400 . ?
C17 H17 0.9400 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C19 C20 1.472(6) 3_666 ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C20 C19 1.472(6) 3_666 ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 115.47(18) . . ?
O1 S1 O3 110.42(17) . . ?
O2 S1 O3 110.7(2) . . ?
O1 S1 C1 107.99(12) . . ?
O2 S1 C1 106.64(13) . . ?
O3 S1 C1 104.95(11) . . ?
C19 O4 C20 108.9(3) . . ?
C18 N1 H1A 109.5 . . ?
C18 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C18 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 C1 C6 120.0(2) . . ?
C2 C1 S1 120.39(17) . . ?
C6 C1 S1 119.56(17) . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 C7 118.6(2) . . ?
C5 C4 C7 122.3(2) . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C8 C7 C4 175.0(3) . . ?
C7 C8 C9 176.4(3) . . ?
C11 C9 C10 118.8(2) . . ?
C11 C9 C8 121.8(2) . . ?
C10 C9 C8 119.3(2) . . ?
C11 C10 C9 120.5(2) 3_567 . ?
C11 C10 H10 119.7 3_567 . ?
C9 C10 H10 119.7 . . ?
C10 C11 C9 120.6(2) 3_567 . ?
C10 C11 H11 119.7 3_567 . ?
C9 C11 H11 119.7 . . ?
C13 C12 C17 118.5(2) . . ?
C13 C12 C18 120.0(3) . . ?
C17 C12 C18 121.6(3) . . ?
C12 C13 C14 120.9(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.2(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.9(3) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
N1 C18 C12 112.3(2) . . ?
N1 C18 H18A 109.1 . . ?
C12 C18 H18A 109.1 . . ?
N1 C18 H18B 109.1 . . ?
C12 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
O4 C19 C20 110.2(3) . 3_666 ?
O4 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 3_666 . ?
O4 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 3_666 . ?
H19A C19 H19B 108.1 . . ?
O4 C20 C19 110.8(3) . 3_666 ?
O4 C20 H20A 109.5 . . ?
C19 C20 H20A 109.5 3_666 . ?
O4 C20 H20B 109.5 . . ?
C19 C20 H20B 109.5 3_666 . ?
H20A C20 H20B 108.1 . . ?

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
O1 S1 C1 C2 0.7(2) . . . . ?
O2 S1 C1 C2 -124.0(2) . . . . ?
O3 S1 C1 C2 118.5(2) . . . . ?
O1 S1 C1 C6 -176.8(2) . . . . ?
O2 S1 C1 C6 58.5(3) . . . . ?
O3 S1 C1 C6 -59.0(2) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
S1 C1 C2 C3 -176.57(18) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C2 C3 C4 C7 176.9(2) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C7 C4 C5 C6 -176.7(2) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
S1 C1 C6 C5 176.69(18) . . . . ?
C11 C9 C10 C11 -0.2(4) . . . 3_567 ?
C8 C9 C10 C11 -179.9(2) . . . 3_567 ?
C10 C9 C11 C10 0.2(4) . . . 3_567 ?
C8 C9 C11 C10 179.9(2) . . . 3_567 ?
C17 C12 C13 C14 0.2(4) . . . . ?
C18 C12 C13 C14 -179.5(3) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
C13 C14 C15 C16 -1.4(4) . . . . ?
C14 C15 C16 C17 1.0(4) . . . . ?
C15 C16 C17 C12 0.0(4) . . . . ?
C13 C12 C17 C16 -0.6(4) . . . . ?
C18 C12 C17 C16 179.1(3) . . . . ?
C13 C12 C18 N1 117.9(3) . . . . ?
C17 C12 C18 N1 -61.8(4) . . . . ?
C20 O4 C19 C20 58.3(4) . . . 3_666 ?
C19 O4 C20 C19 -58.7(4) . . . 3_666 ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O2 . . . 2.788(3) 0.900 1.940 156.3 no
N1 H1B O3 . . 4_666 3.024(4) 0.900 2.140 167.2 no
N1 H1C O3 . . 4_566 3.014(4) 0.900 2.192 151.6 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        BSPEB/benzylamine/dioxane
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/dioxane'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_global
_database_code_depnum_ccdc_archive 'CCDC 1491086'
_audit_update_record             
;
2016-08-02 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;
_audit_creation_date             2016-06-01
_audit_creation_method           'by CrystalStructure 4.2'

#==============================================================================
#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H16 N O3 S'
_chemical_formula_moiety         'C18 H16 N O3 S'
_chemical_formula_weight         326.39
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_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                   5.48472(15)
_cell_length_b                   44.0584(14)
_cell_length_c                   7.7312(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.467(2)
_cell_angle_gamma                90.0000
_cell_volume                     1866.50(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4260
_cell_measurement_theta_min      5.80
_cell_measurement_theta_max      74.39
_cell_measurement_temperature    213
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684.00
_exptl_absorpt_coefficient_mu    1.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.5a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_T_max  0.968

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      213
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            9700
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_theta_max         76.623
_diffrn_reflns_theta_min         4.014
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -55
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3791
_reflns_number_gt                3215
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0819
_refine_ls_wR_factor_ref         0.2291
_refine_ls_wR_factor_gt          0.2240
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3791
_refine_ls_number_parameters     209
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0855P)²+3.2137P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.74
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.92972(16) 0.28855(2) 0.16233(13) 0.0378(3) Uani 1 1 d . . . . .
O1 O 1.1643(7) 0.28214(8) 0.2361(6) 0.0901(14) Uani 1 1 d . . . . .
O2 O 0.7382(7) 0.27058(7) 0.2195(7) 0.0993(16) Uani 1 1 d . . . . .
O3 O 0.9320(9) 0.28772(8) -0.0241(5) 0.0833(13) Uani 1 1 d . . . . .
N1 N 0.4042(6) 0.22775(7) 0.3423(4) 0.0460(8) Uani 1 1 d . . . . .
H1A H 0.3932 0.2475 0.3139 0.055 Uiso 1 1 calc R U . . .
H1B H 0.5463 0.2243 0.4017 0.055 Uiso 1 1 calc R U . . .
H1C H 0.2793 0.2227 0.4082 0.055 Uiso 1 1 calc R U . . .
C1 C 0.8635(6) 0.32659(8) 0.2151(4) 0.0333(7) Uani 1 1 d . . . . .
C2 C 0.6551(7) 0.33341(9) 0.3027(5) 0.0395(8) Uani 1 1 d . . . . .
H2 H 0.5470 0.3179 0.3321 0.047 Uiso 1 1 calc R U . . .
C3 C 0.6074(7) 0.36303(9) 0.3466(5) 0.0449(9) Uani 1 1 d . . . . .
H3 H 0.4683 0.3675 0.4088 0.054 Uiso 1 1 calc R U . . .
C4 C 0.7620(7) 0.38636(9) 0.3003(5) 0.0448(9) Uani 1 1 d . . . . .
C5 C 0.9700(7) 0.37935(9) 0.2102(5) 0.0456(9) Uani 1 1 d . . . . .
H5 H 1.0763 0.3950 0.1787 0.055 Uiso 1 1 calc R U . . .
C6 C 1.0208(7) 0.34969(8) 0.1673(5) 0.0398(8) Uani 1 1 d . . . . .
H6 H 1.1605 0.3451 0.1061 0.048 Uiso 1 1 calc R U . . .
C7 C 0.7070(9) 0.41696(10) 0.3475(7) 0.0585(11) Uani 1 1 d . . . . .
C8 C 0.6486(10) 0.44175(11) 0.3920(8) 0.0686(14) Uani 1 1 d . . . . .
C9 C 0.5733(11) 0.47128(11) 0.4468(8) 0.0719(15) Uani 1 1 d . . . . .
C10 C 0.3681(15) 0.47498(13) 0.5367(11) 0.114(3) Uani 1 1 d . . . . .
H10 H 0.2739 0.4579 0.5623 0.137 Uiso 1 1 calc R U . . .
C11 C 0.7061(15) 0.49668(13) 0.4085(11) 0.113(3) Uani 1 1 d . . . . .
H11 H 0.8476 0.4948 0.3449 0.136 Uiso 1 1 calc R U . . .
C12 C 0.3602(8) 0.17598(9) 0.2199(5) 0.0445(9) Uani 1 1 d . . . . .
C13 C 0.5385(7) 0.15939(10) 0.3103(5) 0.0469(9) Uani 1 1 d . . . . .
H13 H 0.6822 0.1691 0.3513 0.056 Uiso 1 1 calc R U . . .
C14 C 0.5084(8) 0.12887(10) 0.3409(6) 0.0508(10) Uani 1 1 d . . . . .
H14 H 0.6305 0.1180 0.4034 0.061 Uiso 1 1 calc R U . . .
C15 C 0.2996(9) 0.11420(10) 0.2803(6) 0.0553(11) Uani 1 1 d . . . . .
H15 H 0.2799 0.0933 0.2999 0.066 Uiso 1 1 calc R U . . .
C16 C 0.1210(8) 0.13030(11) 0.1912(6) 0.0578(12) Uani 1 1 d . . . . .
H16 H -0.0224 0.1204 0.1512 0.069 Uiso 1 1 calc R U . . .
C17 C 0.1502(8) 0.16115(11) 0.1595(6) 0.0524(10) Uani 1 1 d . . . . .
H17 H 0.0276 0.1720 0.0971 0.063 Uiso 1 1 calc R U . . .
C18 C 0.3944(10) 0.20925(10) 0.1835(6) 0.0598(12) Uani 1 1 d . . . . .
H18A H 0.5461 0.2120 0.1229 0.072 Uiso 1 1 calc R U . . .
H18B H 0.2593 0.2164 0.1068 0.072 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O2 1.402(3) . ?
S1 O1 1.413(3) . ?
S1 O3 1.442(4) . ?
S1 C1 1.767(4) . ?
N1 C18 1.473(5) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N1 H1C 0.9000 . ?
C1 C2 1.386(5) . ?
C1 C6 1.394(5) . ?
C2 C3 1.376(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.389(6) . ?
C3 H3 0.9400 . ?
C4 C5 1.397(6) . ?
C4 C7 1.432(5) . ?
C5 C6 1.380(5) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.193(6) . ?
C8 C9 1.435(6) . ?
C9 C10 1.357(8) . ?
C9 C11 1.375(8) . ?
C10 C11 1.385(7) 3_666 ?
C10 H10 0.9400 . ?
C11 C10 1.385(7) 3_666 ?
C11 H11 0.9400 . ?
C12 C13 1.386(6) . ?
C12 C17 1.387(6) . ?
C12 C18 1.506(6) . ?
C13 C14 1.377(6) . ?
C13 H13 0.9400 . ?
C14 C15 1.380(6) . ?
C14 H14 0.9400 . ?
C15 C16 1.370(7) . ?
C15 H15 0.9400 . ?
C16 C17 1.392(7) . ?
C16 H16 0.9400 . ?
C17 H17 0.9400 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 116.2(3) . . ?
O2 S1 O3 109.9(3) . . ?
O1 S1 O3 110.6(3) . . ?
O2 S1 C1 107.37(19) . . ?
O1 S1 C1 106.80(18) . . ?
O3 S1 C1 105.40(17) . . ?
C18 N1 H1A 109.5 . . ?
C18 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C18 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 C1 C6 120.3(3) . . ?
C2 C1 S1 120.0(3) . . ?
C6 C1 S1 119.7(3) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 C7 119.6(4) . . ?
C5 C4 C7 121.4(4) . . ?
C6 C5 C4 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C8 C7 C4 175.8(6) . . ?
C7 C8 C9 178.7(6) . . ?
C10 C9 C11 118.1(5) . . ?
C10 C9 C8 121.1(5) . . ?
C11 C9 C8 120.8(5) . . ?
C9 C10 C11 121.7(6) . 3_666 ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 3_666 . ?
C9 C11 C10 120.2(6) . 3_666 ?
C9 C11 H11 119.9 . . ?
C10 C11 H11 119.9 3_666 . ?
C13 C12 C17 118.6(4) . . ?
C13 C12 C18 121.1(4) . . ?
C17 C12 C18 120.2(4) . . ?
C14 C13 C12 121.0(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 119.6(4) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.6(4) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C16 120.0(4) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
N1 C18 C12 112.5(3) . . ?
N1 C18 H18A 109.1 . . ?
C12 C18 H18A 109.1 . . ?
N1 C18 H18B 109.1 . . ?
C12 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C1 C2 1.8(4) . . . . ?
O1 S1 C1 C2 -123.5(4) . . . . ?
O3 S1 C1 C2 118.9(3) . . . . ?
O2 S1 C1 C6 -177.7(4) . . . . ?
O1 S1 C1 C6 57.0(4) . . . . ?
O3 S1 C1 C6 -60.6(4) . . . . ?
C6 C1 C2 C3 -1.8(5) . . . . ?
S1 C1 C2 C3 178.7(3) . . . . ?
C1 C2 C3 C4 1.7(6) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C2 C3 C4 C7 179.9(4) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C7 C4 C5 C6 179.4(4) . . . . ?
C4 C5 C6 C1 -0.4(6) . . . . ?
C2 C1 C6 C5 1.1(6) . . . . ?
S1 C1 C6 C5 -179.3(3) . . . . ?
C11 C9 C10 C11 -1.0(15) . . . 3_666 ?
C8 C9 C10 C11 179.6(8) . . . 3_666 ?
C10 C9 C11 C10 1.0(14) . . . 3_666 ?
C8 C9 C11 C10 -179.6(7) . . . 3_666 ?
C17 C12 C13 C14 -0.4(6) . . . . ?
C18 C12 C13 C14 -178.9(4) . . . . ?
C12 C13 C14 C15 0.6(6) . . . . ?
C13 C14 C15 C16 -0.8(7) . . . . ?
C14 C15 C16 C17 0.9(7) . . . . ?
C13 C12 C17 C16 0.5(6) . . . . ?
C18 C12 C17 C16 179.0(4) . . . . ?
C15 C16 C17 C12 -0.8(7) . . . . ?
C13 C12 C18 N1 -65.6(6) . . . . ?
C17 C12 C18 N1 115.9(5) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O1 . . 1_455 2.838(5) 0.900 2.049 145.7 no
N1 H1A O2 . . . 2.822(5) 0.900 2.294 117.3 no
N1 H1C O3 . . 4_466 2.911(6) 0.900 2.049 160.0 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        BSPEB/benzylamine
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/dioxane'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_global
_database_code_depnum_ccdc_archive 'CCDC 1491236'
_audit_update_record             
;
2016-08-02 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;
_audit_creation_date             2016-07-07
_audit_creation_method           'by CrystalStructure 4.2'

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

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H22 N O5 S'
_chemical_formula_moiety         'C20 H22 N O5 S'
_chemical_formula_weight         388.46
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.76413(11)
_cell_length_b                   7.92695(17)
_cell_length_c                   21.2914(5)
_cell_angle_alpha                87.5578(18)
_cell_angle_beta                 82.2517(18)
_cell_angle_gamma                84.7236(17)
_cell_volume                     959.43(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5770
_cell_measurement_theta_min      5.60
_cell_measurement_theta_max      76.63
_cell_measurement_temperature    213
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             410.00
_exptl_absorpt_coefficient_mu    1.768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.5a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.706
_exptl_absorpt_correction_T_max  0.915

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      213
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            9857
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_theta_max         77.397
_diffrn_reflns_theta_min         5.608
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3899
_reflns_number_gt                3485
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1343
_refine_ls_wR_factor_gt          0.1308
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3899
_refine_ls_number_parameters     253
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0624P)²+0.3885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.51
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.54916(8) 0.16310(6) 0.59067(2) 0.03600(15) Uani 1 1 d . . . . .
O1 O 0.6811(4) 0.2650(2) 0.54377(7) 0.0745(6) Uani 1 1 d . . . . .
O2 O 0.6348(3) -0.0135(2) 0.58910(9) 0.0663(5) Uani 1 1 d . . . . .
O3 O 0.2996(3) 0.1824(2) 0.58836(7) 0.0613(5) Uani 1 1 d . . . . .
O4 O 0.5692(6) 0.0525(3) 1.05495(11) 0.1029(9) Uani 1 1 d . . . . .
O5 O 0.7853(5) 0.6229(3) 0.53675(13) 0.0865(8) Uani 1 1 d . . . . .
N1 N 0.8796(3) 0.1502(2) 0.42490(8) 0.0491(4) Uani 1 1 d . . . . .
H1A H 0.8395 0.1810 0.4654 0.059 Uiso 1 1 calc R U . . .
H1B H 1.0364 0.1266 0.4172 0.059 Uiso 1 1 calc R U . . .
H1C H 0.8077 0.0577 0.4183 0.059 Uiso 1 1 calc R U . . .
C1 C 0.5969(3) 0.2349(2) 0.66511(8) 0.0320(4) Uani 1 1 d . . . . .
C2 C 0.7958(3) 0.3179(2) 0.66945(9) 0.0374(4) Uani 1 1 d . . . . .
H2 H 0.8995 0.3417 0.6328 0.045 Uiso 1 1 calc R U . . .
C3 C 0.8398(3) 0.3652(2) 0.72796(9) 0.0397(4) Uani 1 1 d . . . . .
H3 H 0.9739 0.4219 0.7310 0.048 Uiso 1 1 calc R U . . .
C4 C 0.6881(3) 0.3302(2) 0.78274(9) 0.0367(4) Uani 1 1 d . . . . .
C5 C 0.4876(3) 0.2476(3) 0.77751(9) 0.0407(4) Uani 1 1 d . . . . .
H5 H 0.3830 0.2244 0.8140 0.049 Uiso 1 1 calc R U . . .
C6 C 0.4426(3) 0.2001(2) 0.71896(9) 0.0373(4) Uani 1 1 d . . . . .
H6 H 0.3079 0.1443 0.7156 0.045 Uiso 1 1 calc R U . . .
C7 C 0.7468(4) 0.3738(3) 0.84306(10) 0.0426(4) Uani 1 1 d . . . . .
C8 C 0.8131(4) 0.4095(3) 0.89114(10) 0.0423(4) Uani 1 1 d . . . . .
C9 C 0.9052(3) 0.4546(2) 0.94665(9) 0.0367(4) Uani 1 1 d . . . . .
C10 C 0.7908(3) 0.4235(2) 1.00728(9) 0.0402(4) Uani 1 1 d . . . . .
H10 H 0.6492 0.3713 1.0123 0.048 Uiso 1 1 calc R U . . .
C11 C 0.8832(4) 0.4687(2) 1.06004(9) 0.0405(4) Uani 1 1 d . . . . .
H11 H 0.8036 0.4477 1.1007 0.049 Uiso 1 1 calc R U . . .
C12 C 0.8235(3) 0.2393(2) 0.31426(9) 0.0395(4) Uani 1 1 d . . . . .
C13 C 1.0225(4) 0.1504(3) 0.28330(10) 0.0461(5) Uani 1 1 d . . . . .
H13 H 1.1524 0.1198 0.3050 0.055 Uiso 1 1 calc R U . . .
C14 C 1.0304(4) 0.1069(3) 0.22087(11) 0.0519(5) Uani 1 1 d . . . . .
H14 H 1.1657 0.0469 0.2003 0.062 Uiso 1 1 calc R U . . .
C15 C 0.8408(4) 0.1511(3) 0.18851(10) 0.0525(5) Uani 1 1 d . . . . .
H15 H 0.8458 0.1200 0.1462 0.063 Uiso 1 1 calc R U . . .
C16 C 0.6446(4) 0.2409(3) 0.21848(11) 0.0533(5) Uani 1 1 d . . . . .
H16 H 0.5160 0.2729 0.1964 0.064 Uiso 1 1 calc R U . . .
C17 C 0.6361(4) 0.2842(3) 0.28103(11) 0.0472(5) Uani 1 1 d . . . . .
H17 H 0.5009 0.3451 0.3012 0.057 Uiso 1 1 calc R U . . .
C18 C 0.8067(5) 0.2896(3) 0.38206(11) 0.0562(6) Uani 1 1 d . . . . .
H18A H 0.9054 0.3830 0.3842 0.067 Uiso 1 1 calc R U . . .
H18B H 0.6439 0.3314 0.3968 0.067 Uiso 1 1 calc R U . . .
C19 C 0.6805(6) -0.0891(4) 1.0237(2) 0.0919(12) Uani 1 1 d . . . . .
H19A H 0.6055 -0.1905 1.0407 0.110 Uiso 1 1 calc R U . . .
H19B H 0.8456 -0.1036 1.0309 0.110 Uiso 1 1 calc R U . . .
C20 C 0.3329(8) 0.0703(4) 1.0431(2) 0.1025(14) Uani 1 1 d . . . . .
H20A H 0.2509 0.1699 1.0646 0.123 Uiso 1 1 calc R U . . .
H20B H 0.2548 -0.0296 1.0602 0.123 Uiso 1 1 calc R U . . .
H4 H 0.753(8) 0.528(7) 0.536(2) 0.133(17) Uiso 1 1 d . . . . .
H7 H 0.745(8) 0.669(6) 0.501(2) 0.130(16) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O1 1.4382(16) . ?
S1 O3 1.4400(16) . ?
S1 O2 1.4415(16) . ?
S1 C1 1.7706(18) . ?
O4 C19 1.389(4) . ?
O4 C20 1.412(5) . ?
O5 H4 0.80(5) . ?
O5 H7 0.88(5) . ?
N1 C18 1.470(3) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N1 H1C 0.9000 . ?
C1 C6 1.388(2) . ?
C1 C2 1.389(3) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.395(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.398(3) . ?
C4 C7 1.435(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.193(3) . ?
C8 C9 1.431(3) . ?
C9 C10 1.391(3) . ?
C9 C11 1.400(3) 2_767 ?
C10 C11 1.380(3) . ?
C10 H10 0.9400 . ?
C11 C9 1.400(3) 2_767 ?
C11 H11 0.9400 . ?
C12 C17 1.381(3) . ?
C12 C13 1.391(3) . ?
C12 C18 1.502(3) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9400 . ?
C15 C16 1.374(3) . ?
C15 H15 0.9400 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9400 . ?
C17 H17 0.9400 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C19 C20 1.435(6) 2_657 ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C20 C19 1.435(6) 2_657 ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O3 113.85(13) . . ?
O1 S1 O2 112.56(12) . . ?
O3 S1 O2 110.42(11) . . ?
O1 S1 C1 105.90(9) . . ?
O3 S1 C1 107.31(8) . . ?
O2 S1 C1 106.26(9) . . ?
C19 O4 C20 108.0(2) . . ?
H4 O5 H7 104(4) . . ?
C18 N1 H1A 109.5 . . ?
C18 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C18 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C6 C1 C2 120.62(17) . . ?
C6 C1 S1 119.86(14) . . ?
C2 C1 S1 119.43(14) . . ?
C3 C2 C1 119.40(17) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.91(17) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 118.99(17) . . ?
C3 C4 C7 119.09(18) . . ?
C5 C4 C7 121.88(18) . . ?
C6 C5 C4 120.34(17) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.73(17) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C8 C7 C4 175.0(2) . . ?
C7 C8 C9 176.6(2) . . ?
C10 C9 C11 118.97(17) . 2_767 ?
C10 C9 C8 121.76(18) . . ?
C11 C9 C8 119.27(18) 2_767 . ?
C11 C10 C9 120.60(18) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C9 120.43(18) . 2_767 ?
C10 C11 H11 119.8 . . ?
C9 C11 H11 119.8 2_767 . ?
C17 C12 C13 118.55(19) . . ?
C17 C12 C18 119.09(19) . . ?
C13 C12 C18 122.35(19) . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.1(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 120.9(2) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
N1 C18 C12 113.42(17) . . ?
N1 C18 H18A 108.9 . . ?
C12 C18 H18A 108.9 . . ?
N1 C18 H18B 108.9 . . ?
C12 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
O4 C19 C20 110.4(3) . 2_657 ?
O4 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 2_657 . ?
O4 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 2_657 . ?
H19A C19 H19B 108.1 . . ?
O4 C20 C19 110.8(3) . 2_657 ?
O4 C20 H20A 109.5 . . ?
C19 C20 H20A 109.5 2_657 . ?
O4 C20 H20B 109.5 . . ?
C19 C20 H20B 109.5 2_657 . ?
H20A C20 H20B 108.1 . . ?

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
O1 S1 C1 C6 160.54(17) . . . . ?
O3 S1 C1 C6 38.59(18) . . . . ?
O2 S1 C1 C6 -79.54(17) . . . . ?
O1 S1 C1 C2 -22.81(18) . . . . ?
O3 S1 C1 C2 -144.76(16) . . . . ?
O2 S1 C1 C2 97.10(17) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
S1 C1 C2 C3 -176.34(14) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C2 C3 C4 C7 176.81(18) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C7 C4 C5 C6 -176.80(18) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
S1 C1 C6 C5 176.27(15) . . . . ?
C11 C9 C10 C11 0.5(3) 2_767 . . . ?
C8 C9 C10 C11 -179.87(18) . . . . ?
C9 C10 C11 C9 -0.5(3) . . . 2_767 ?
C17 C12 C13 C14 -0.6(3) . . . . ?
C18 C12 C13 C14 -179.9(2) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C14 C15 C16 C17 -1.0(4) . . . . ?
C13 C12 C17 C16 0.5(3) . . . . ?
C18 C12 C17 C16 179.8(2) . . . . ?
C15 C16 C17 C12 0.4(3) . . . . ?
C17 C12 C18 N1 132.6(2) . . . . ?
C13 C12 C18 N1 -48.1(3) . . . . ?
C20 O4 C19 C20 58.7(4) . . . 2_657 ?
C19 O4 C20 C19 -59.0(4) . . . 2_657 ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O5 H4 O1 . . . 2.947(3) 0.80(5) 2.15(5) 174(5) no
N1 H1A O1 . . . 2.787(2) 0.900 1.906 165.6 no
N1 H1B O2 . . 2_756 2.888(3) 0.900 2.011 164.6 no
N1 H1B O5 . . 2_766 2.970(3) 0.900 2.602 105.3 no
N1 H1C O3 . . 2_656 2.956(3) 0.900 2.070 167.8 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        BSPEB/benzylamine/dioxane
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/dioxane'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_tetsCO23
_database_code_depnum_ccdc_archive 'CCDC 1544668'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_I                   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.862 Note  
RESPONSE: The crystal was collected by insering it into
 a 0.3 mm diameter quartz capillary and sealed under a CO2 
 pressure. The hindrance caused by the capillary and 
 intrument geometry prevented the complete data collection.
;
_vrf_PLAT082_I                   
;
PROBLEM: High R1 Value ..................................       0.25 Report
RESPONSE: The crystal was preliminary evacuated by applying high vacuum 
 at the temperature of 80 \%C overnight. It was then inserted into
 a 0.3 mm diameter quartz capillary and sealed under a 20 bar CO2 
 pressure. These treatments caused a significant decrease of the
 crystal quality, which severely affected the data quality.
;
_vrf_PLAT084_I                   
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.66 Report
RESPONSE: The crystal was preliminary evacuated by applying high vacuum 
 at the temperature of 80 \%C overnight. It was then inserted into
 a 0.3 mm diameter quartz capillary and sealed under a 20 bar CO2 
 pressure. These treatments caused a significant decrease of the
 crystal quality, which severely affected the data quality.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H34 N2 O6 S2, 2(C O2)'
_chemical_formula_sum            'C38 H32 N2 O10 S2'
_chemical_formula_weight         740.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1210 0.1210 '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                   5.6220(6)
_cell_length_b                   7.3146(6)
_cell_length_c                   22.8362(13)
_cell_angle_alpha                85.588(6)
_cell_angle_beta                 85.910(6)
_cell_angle_gamma                89.677(7)
_cell_volume                     933.92(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    11527
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.94

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             386
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.195
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'AIMLESS CCP4 code'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  'Huber 4-circles Kappa Goniometer, Pilatus 2M'
_diffrn_measurement_method       'Rotating crystal'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8219
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.650
_diffrn_reflns_theta_max         25.943
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measured_fraction_theta_full 0.862
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_Laue_measured_fraction_full 0.862
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_point_group_measured_fraction_full 0.862
_reflns_number_total             3258
_reflns_number_gt                2992
_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.
 The crystal was preliminary evacuated by applying high vacuum 
 at the temperature of 80 °C overnight. It was then inserted into
 a 0.3 mm diameter quartz capillary and sealed under a 20 bar CO2 
 pressure. These treatments caused a significant decrease of the
 crystal quality, which severely affected the data quality. 
 
;

_computing_data_collection       'Elettra XRD1 data collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)-CCP4 (Evans, 2013)'
_computing_structure_solution    'ShelxT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.3000P)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_number_reflns         3258
_refine_ls_number_parameters     209
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.2578
_refine_ls_R_factor_gt           0.2515
_refine_ls_wR_factor_ref         0.6613
_refine_ls_wR_factor_gt          0.6528
_refine_ls_goodness_of_fit_ref   2.600
_refine_ls_restrained_S_all      2.599
_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 0.1508(4) 0.2372(3) 0.08226(9) 0.0346(11) Uani 1 1 d . . . . .
O3 O 0.4114(14) 0.2388(13) 0.0792(3) 0.051(2) Uani 1 1 d . . . . .
N1 N 0.6927(16) 0.2602(10) -0.0299(3) 0.0371(19) Uani 1 1 d . . . . .
H1A H 0.7722 0.1565 -0.0351 0.056 Uiso 1 1 calc R U . . .
H1B H 0.6498 0.2659 0.0082 0.056 Uiso 1 1 calc R U . . .
H1C H 0.7858 0.3554 -0.0424 0.056 Uiso 1 1 calc R U . . .
O2 O 0.0473(16) 0.4084(9) 0.0595(3) 0.050(2) Uani 1 1 d . . . . .
C1 C 0.0521(19) 0.1996(13) 0.1574(4) 0.039(2) Uani 1 1 d . . . . .
C2 C -0.178(2) 0.1206(14) 0.1718(5) 0.049(3) Uani 1 1 d . . . . .
H2 H -0.2726 0.0872 0.1425 0.059 Uiso 1 1 calc R U . . .
C3 C -0.259(2) 0.0947(15) 0.2324(5) 0.050(3) Uani 1 1 d . . . . .
H3 H -0.4095 0.0457 0.2436 0.060 Uiso 1 1 calc R U . . .
C4 C -0.108(3) 0.1445(17) 0.2750(5) 0.055(3) Uani 1 1 d . . . . .
C5 C 0.115(2) 0.2317(15) 0.2593(5) 0.047(3) Uani 1 1 d . . . . .
H5 H 0.2091 0.2697 0.2880 0.057 Uiso 1 1 calc R U . . .
C6 C 0.186(2) 0.2583(14) 0.2005(5) 0.042(2) Uani 1 1 d . . . . .
H6 H 0.3298 0.3180 0.1895 0.051 Uiso 1 1 calc R U . . .
C13 C 0.5224(18) 0.2983(12) -0.1282(5) 0.0394(16) Uani 1 1 d . . . . .
C14 C 0.3440(18) 0.3827(12) -0.1606(5) 0.0394(16) Uani 1 1 d . . . . .
H14 H 0.2072 0.4249 -0.1406 0.047 Uiso 1 1 calc R U . . .
C15 C 0.364(2) 0.4051(17) -0.2212(6) 0.052(3) Uani 1 1 d . . . . .
H15 H 0.2430 0.4612 -0.2417 0.063 Uiso 1 1 calc R U . . .
C16 C 0.573(2) 0.3415(15) -0.2520(5) 0.047(3) Uani 1 1 d . . . . .
H16 H 0.5875 0.3533 -0.2929 0.056 Uiso 1 1 calc R U . . .
C17 C 0.757(2) 0.2608(13) -0.2206(5) 0.048(3) Uani 1 1 d . . . . .
H17 H 0.8976 0.2255 -0.2406 0.057 Uiso 1 1 calc R U . . .
C18 C 0.7300(18) 0.2347(12) -0.1616(5) 0.0394(16) Uani 1 1 d . . . . .
H18 H 0.8490 0.1735 -0.1416 0.047 Uiso 1 1 calc R U . . .
O1 O 0.0593(19) 0.0843(10) 0.0540(3) 0.056(2) Uani 1 1 d . . . . .
C12 C 0.480(2) 0.2649(17) -0.0633(6) 0.060(3) Uani 1 1 d . . . . .
H12A H 0.3969 0.1488 -0.0548 0.072 Uiso 1 1 calc R U . . .
H12B H 0.3745 0.3600 -0.0492 0.072 Uiso 1 1 calc R U . . .
C9 C -0.399(3) 0.046(2) 0.4426(5) 0.079(5) Uani 1 1 d . . . . .
C7 C -0.194(2) 0.1127(18) 0.3369(5) 0.057(3) Uani 1 1 d . . . . .
C11 C -0.286(3) 0.095(2) 0.4924(6) 0.077(4) Uani 1 1 d . . . . .
H11 H -0.1427 0.1592 0.4864 0.092 Uiso 1 1 calc R U . . .
C10 C -0.624(4) -0.054(3) 0.4509(7) 0.088(5) Uani 1 1 d . . . . .
H10 H -0.7022 -0.0888 0.4191 0.106 Uiso 1 1 calc R U . . .
C8 C -0.290(3) 0.076(2) 0.3844(6) 0.078(5) Uani 1 1 d . . . . .
O1C O 0.064(7) 0.425(5) -0.3758(15) 0.237(14) Uiso 1 1 d D . . . .
C1C C 0.268(8) 0.452(10) -0.386(3) 0.28(3) Uiso 1 1 d D . . . .
O2C O 0.454(9) 0.499(9) -0.407(3) 0.39(3) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.449(8) . ?
S1 O2 1.453(7) . ?
S1 O3 1.462(8) . ?
S1 C1 1.766(9) . ?
N1 C12 1.464(17) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C1 C6 1.378(15) . ?
C1 C2 1.428(16) . ?
C2 C3 1.425(16) . ?
C2 H2 0.9300 . ?
C3 C4 1.407(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.418(18) . ?
C4 C7 1.462(14) . ?
C5 C6 1.374(14) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C13 C14 1.402(13) . ?
C13 C18 1.443(14) . ?
C13 C12 1.486(16) . ?
C14 C15 1.377(16) . ?
C14 H14 0.9300 . ?
C15 C16 1.418(18) . ?
C15 H15 0.9300 . ?
C16 C17 1.402(16) . ?
C16 H16 0.9300 . ?
C17 C18 1.346(15) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C9 C11 1.41(2) . ?
C9 C10 1.46(3) . ?
C9 C8 1.426(17) . ?
C7 C8 1.186(17) . ?
C11 C10 1.37(2) 2_456 ?
C11 H11 0.9300 . ?
C10 C11 1.37(2) 2_456 ?
C10 H10 0.9300 . ?
O1C C1C 1.173(19) . ?
C1C O2C 1.163(19) . ?

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
O1 S1 O2 110.5(5) . . ?
O1 S1 O3 111.9(6) . . ?
O2 S1 O3 113.6(5) . . ?
O1 S1 C1 105.5(5) . . ?
O2 S1 C1 108.0(4) . . ?
O3 S1 C1 107.0(4) . . ?
C12 N1 H1A 109.5 . . ?
C12 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C12 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C6 C1 C2 121.0(10) . . ?
C6 C1 S1 120.7(9) . . ?
C2 C1 S1 118.2(8) . . ?
C3 C2 C1 117.9(11) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 118.8(12) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 121.9(10) . . ?
C5 C4 C7 120.4(12) . . ?
C3 C4 C7 117.6(13) . . ?
C6 C5 C4 117.8(10) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
C1 C6 C5 122.2(11) . . ?
C1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C14 C13 C18 116.5(9) . . ?
C14 C13 C12 119.2(9) . . ?
C18 C13 C12 124.0(9) . . ?
C15 C14 C13 122.2(10) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C14 C15 C16 119.1(10) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 119.9(11) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 119.9(11) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 122.2(9) . . ?
C17 C18 H18 118.9 . . ?
C13 C18 H18 118.9 . . ?
C13 C12 N1 115.8(9) . . ?
C13 C12 H12A 108.3 . . ?
N1 C12 H12A 108.3 . . ?
C13 C12 H12B 108.3 . . ?
N1 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C11 C9 C10 119.3(14) . . ?
C11 C9 C8 121.9(19) . . ?
C10 C9 C8 118.5(16) . . ?
C8 C7 C4 171.2(17) . . ?
C10 C11 C9 123.4(19) 2_456 . ?
C10 C11 H11 118.3 2_456 . ?
C9 C11 H11 118.3 . . ?
C11 C10 C9 117.3(18) 2_456 . ?
C11 C10 H10 121.3 2_456 . ?
C9 C10 H10 121.3 . . ?
C7 C8 C9 175.6(19) . . ?
O2C C1C O1C 165(9) . . ?

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
O1 S1 C1 C6 148.9(8) . . . . ?
O2 S1 C1 C6 -93.0(9) . . . . ?
O3 S1 C1 C6 29.6(9) . . . . ?
O1 S1 C1 C2 -36.2(9) . . . . ?
O2 S1 C1 C2 81.9(9) . . . . ?
O3 S1 C1 C2 -155.5(8) . . . . ?
C6 C1 C2 C3 -3.6(15) . . . . ?
S1 C1 C2 C3 -178.5(7) . . . . ?
C1 C2 C3 C4 -1.1(15) . . . . ?
C2 C3 C4 C5 4.7(16) . . . . ?
C2 C3 C4 C7 -178.7(10) . . . . ?
C3 C4 C5 C6 -3.4(17) . . . . ?
C7 C4 C5 C6 -179.9(10) . . . . ?
C2 C1 C6 C5 5.1(15) . . . . ?
S1 C1 C6 C5 179.9(8) . . . . ?
C4 C5 C6 C1 -1.6(16) . . . . ?
C18 C13 C14 C15 -0.3(14) . . . . ?
C12 C13 C14 C15 -175.0(10) . . . . ?
C13 C14 C15 C16 -0.2(16) . . . . ?
C14 C15 C16 C17 -1.4(17) . . . . ?
C15 C16 C17 C18 3.7(16) . . . . ?
C16 C17 C18 C13 -4.3(15) . . . . ?
C14 C13 C18 C17 2.6(14) . . . . ?
C12 C13 C18 C17 177.0(10) . . . . ?
C14 C13 C12 N1 -152.3(9) . . . . ?
C18 C13 C12 N1 33.5(15) . . . . ?
C10 C9 C11 C10 0(3) . . . 2_456 ?
C8 C9 C11 C10 -174.3(16) . . . 2_456 ?
C11 C9 C10 C11 0(3) . . . 2_456 ?
C8 C9 C10 C11 174.5(15) . . . 2_456 ?

_refine_diff_density_max         1.850
_refine_diff_density_min         -1.123
_refine_diff_density_rms         0.319



