# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 1486135'
_audit_update_record             
;
2016-06-17 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H N O S'
_chemical_formula_weight         75.09

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

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.924(5)
_cell_length_b                   8.289(2)
_cell_length_c                   15.498(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.130(6)
_cell_angle_gamma                90.00
_cell_volume                     2019.7(11)
_cell_formula_units_Z            26
_cell_measurement_temperature    566(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             988
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      566(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16179
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.30
_diffrn_reflns_theta_max         25.27
_reflns_number_total             3567
_reflns_number_gt                2926
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.37(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3567
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0802
_refine_ls_wR_factor_ref         0.2515
_refine_ls_wR_factor_gt          0.2216
_refine_ls_goodness_of_fit_ref   1.754
_refine_ls_restrained_S_all      1.754
_refine_ls_shift/su_max          0.061
_refine_ls_shift/su_mean         0.013

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.16134(5) 0.02640(9) 0.14060(6) 0.0668(4) Uani 1 1 d . . .
O1 O 0.22343(13) 0.1424(3) 0.20128(15) 0.0717(7) Uani 1 1 d . . .
C2 C 0.07046(17) 0.1443(3) 0.10350(19) 0.0593(7) Uani 1 1 d . . .
O3 O 0.13914(15) -0.0947(3) 0.19753(18) 0.0858(8) Uani 1 1 d . . .
C4 C 0.26186(17) 0.2724(4) 0.1598(2) 0.0637(8) Uani 1 1 d . . .
O5 O 0.19793(16) -0.0177(3) 0.06647(19) 0.0871(8) Uani 1 1 d . . .
C6 C 0.34091(19) 0.5269(4) 0.0909(2) 0.0677(8) Uani 1 1 d . . .
N7 N 0.01545(18) 0.1311(3) 0.24613(19) 0.0728(8) Uani 1 1 d . . .
C8 C 0.00700(17) 0.1783(4) 0.15288(17) 0.0582(7) Uani 1 1 d . . .
C9 C 0.2673(2) 0.5488(4) 0.1266(2) 0.0692(9) Uani 1 1 d . . .
H9A H 0.2443 0.6519 0.1271 0.083 Uiso 1 1 calc R . .
O10 O -0.04175(19) 0.0550(4) 0.26806(19) 0.1009(10) Uani 1 1 d . . .
C11 C 0.0585(2) 0.2002(4) 0.0174(2) 0.0706(9) Uani 1 1 d . . .
H11A H 0.0994 0.1796 -0.0179 0.085 Uiso 1 1 calc R . .
O12 O 0.07836(19) 0.1733(4) 0.29548(17) 0.1003(9) Uani 1 1 d . . .
C13 C 0.22710(17) 0.4227(4) 0.1614(2) 0.0643(8) Uani 1 1 d . . .
H13A H 0.1778 0.4396 0.1853 0.077 Uiso 1 1 calc R . .
C14 C 0.33489(19) 0.2456(4) 0.1263(2) 0.0752(10) Uani 1 1 d . . .
H14A H 0.3584 0.1427 0.1275 0.090 Uiso 1 1 calc R . .
C15 C 0.3731(2) 0.3718(4) 0.0911(3) 0.0770(10) Uani 1 1 d . . .
H15A H 0.4220 0.3530 0.0667 0.092 Uiso 1 1 calc R . .
C16 C -0.0651(2) 0.2607(5) 0.1201(2) 0.0737(9) Uani 1 1 d . . .
H16A H -0.1072 0.2784 0.1543 0.088 Uiso 1 1 calc R . .
C17 C -0.0746(2) 0.3174(5) 0.0354(2) 0.0825(10) Uani 1 1 d . . .
H17A H -0.1226 0.3772 0.0130 0.099 Uiso 1 1 calc R . .
O18 O 0.4584(2) 0.8510(4) -0.0780(3) 0.1228(12) Uani 1 1 d . . .
C19 C 0.3843(3) 0.8613(6) -0.0707(3) 0.0931(12) Uani 1 1 d . . .
C20 C 0.3861(2) 0.6643(4) 0.0534(2) 0.0752(9) Uani 1 1 d . . .
H20A H 0.4371 0.6159 0.0365 0.090 Uiso 1 1 calc R . .
C21 C -0.0142(2) 0.2862(5) -0.0158(2) 0.0815(10) Uani 1 1 d . . .
H21A H -0.0218 0.3229 -0.0732 0.098 Uiso 1 1 calc R . .
C22 C 0.4183(3) 0.7867(5) 0.1211(3) 0.0998(13) Uani 1 1 d . . .
H22A H 0.4029 0.8947 0.1140 0.120 Uiso 1 1 calc R . .
C23 C 0.3364(3) 0.7283(6) -0.0299(3) 0.0942(12) Uani 1 1 d . . .
H23A H 0.2849 0.7781 -0.0147 0.113 Uiso 1 1 calc R . .
C24 C 0.3337(4) 1.0044(8) -0.1033(5) 0.148(3) Uani 1 1 d . . .
H24A H 0.3692 1.0796 -0.1279 0.221 Uiso 1 1 calc R . .
H24B H 0.3116 1.0548 -0.0558 0.221 Uiso 1 1 calc R . .
H24C H 0.2874 0.9720 -0.1473 0.221 Uiso 1 1 calc R . .
C25 C 0.3074(3) 0.6069(7) -0.1018(3) 0.1128(15) Uani 1 1 d . . .
H25A H 0.2765 0.5215 -0.0791 0.169 Uiso 1 1 calc R . .
H25B H 0.3561 0.5629 -0.1229 0.169 Uiso 1 1 calc R . .
H25C H 0.2712 0.6594 -0.1489 0.169 Uiso 1 1 calc R . .
C26 C 0.4753(4) 0.7311(7) 0.1997(4) 0.1341(19) Uani 1 1 d . . .
H26A H 0.4906 0.8209 0.2381 0.201 Uiso 1 1 calc R . .
H26B H 0.5256 0.6851 0.1830 0.201 Uiso 1 1 calc R . .
H26C H 0.4467 0.6511 0.2292 0.201 Uiso 1 1 calc R . .


_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 O3 1.418(2) . ?
S1 O5 1.416(2) . ?
S1 O1 1.579(2) . ?
S1 C2 1.765(3) . ?
O1 C4 1.440(4) . ?
C2 C8 1.390(4) . ?
C2 C11 1.397(4) . ?
C4 C13 1.365(4) . ?
C4 C14 1.365(4) . ?
C6 C9 1.385(4) . ?
C6 C15 1.384(5) . ?
C6 C20 1.511(4) . ?
N7 O10 1.201(3) . ?
N7 O12 1.212(4) . ?
N7 C8 1.483(4) . ?
C8 C16 1.363(4) . ?
C9 C13 1.380(5) . ?
C11 C21 1.387(5) . ?
C14 C15 1.367(5) . ?
C16 C17 1.380(5) . ?
C17 C21 1.365(5) . ?
O18 C19 1.206(5) . ?
C19 C24 1.477(7) . ?
C19 C23 1.533(6) . ?
C20 C22 1.491(6) . ?
C20 C23 1.501(6) . ?
C22 C26 1.472(7) . ?
C23 C25 1.518(6) . ?

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
O3 S1 O5 119.84(17) . . ?
O3 S1 O1 104.78(15) . . ?
O5 S1 O1 109.94(14) . . ?
O3 S1 C2 108.80(14) . . ?
O5 S1 C2 107.47(16) . . ?
O1 S1 C2 105.09(13) . . ?
C4 O1 S1 117.40(19) . . ?
C8 C2 C11 117.3(3) . . ?
C8 C2 S1 124.3(2) . . ?
C11 C2 S1 118.4(2) . . ?
C13 C4 C14 121.9(3) . . ?
C13 C4 O1 118.2(2) . . ?
C14 C4 O1 119.7(3) . . ?
C9 C6 C15 117.2(3) . . ?
C9 C6 C20 122.6(3) . . ?
C15 C6 C20 120.2(3) . . ?
O10 N7 O12 124.2(3) . . ?
O10 N7 C8 117.3(3) . . ?
O12 N7 C8 118.5(2) . . ?
C16 C8 C2 122.7(3) . . ?
C16 C8 N7 115.8(2) . . ?
C2 C8 N7 121.5(3) . . ?
C6 C9 C13 122.1(3) . . ?
C2 C11 C21 120.2(3) . . ?
C4 C13 C9 118.0(3) . . ?
C4 C14 C15 119.2(3) . . ?
C14 C15 C6 121.6(3) . . ?
C8 C16 C17 118.9(3) . . ?
C21 C17 C16 120.5(3) . . ?
O18 C19 C24 120.9(4) . . ?
O18 C19 C23 123.1(4) . . ?
C24 C19 C23 116.0(4) . . ?
C22 C20 C23 116.2(3) . . ?
C22 C20 C6 112.0(3) . . ?
C23 C20 C6 112.3(3) . . ?
C17 C21 C11 120.4(3) . . ?
C26 C22 C20 117.9(4) . . ?
C20 C23 C25 117.1(4) . . ?
C20 C23 C19 112.4(3) . . ?
C25 C23 C19 106.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        25.27
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.075
