# 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_blp1
_database_code_depnum_ccdc_archive 'CCDC 1534334'
_audit_update_record             
;
2017-02-22 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H26 O2'
_chemical_formula_sum            'C14 H26 O2'
_chemical_formula_weight         226.35
_chemical_absolute_configuration ad

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   7.2799(7)
_cell_length_b                   11.4069(11)
_cell_length_c                   16.0415(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1332.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourles
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9645
_exptl_absorpt_correction_T_max  0.9856
_exptl_absorpt_process_details   
;
 Siemens SADABS program multi-scan Version 2008/1
 Blessing, Acta Cryst. (1995) A51 33-38 
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24726
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         26.13
_reflns_number_total             2635
_reflns_number_gt                2100
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instr. Service v2010, 1-2'
_computing_cell_refinement       'SAINT V7.68A (Bruker, 2009) in Apex2 suite'
_computing_data_reduction        'SAINT and XPREP Version 2008/2 (Bruker)'
_computing_structure_solution    'XS Version 2008/1'
_computing_structure_refinement  'XL Version 2008/4'

_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)+(0.0968P)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    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.027(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.1(19)
_refine_ls_number_reflns         2635
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1487
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C8 C 0.9702(3) 0.7740(2) 0.16990(14) 0.0338(5) Uani 1 1 d . . .
H8A H 0.9139 0.8525 0.1807 0.041 Uiso 1 1 calc R . .
O1 O 0.9841(2) 0.75507(14) 0.08142(10) 0.0401(5) Uani 1 1 d . . .
H1A H 1.0740 0.7111 0.0714 0.060 Uiso 1 1 calc R . .
O2 O 0.2663(2) 0.37599(15) 0.50446(10) 0.0397(5) Uani 1 1 d . . .
H2A H 0.1941 0.3621 0.4648 0.060 Uiso 1 1 calc R . .
C9 C 1.1634(3) 0.7709(2) 0.20618(15) 0.0352(6) Uani 1 1 d . . .
H9A H 1.2383 0.8339 0.1808 0.042 Uiso 1 1 calc R . .
H9B H 1.2219 0.6948 0.1928 0.042 Uiso 1 1 calc R . .
C11 C 1.1576(3) 0.7873(2) 0.30092(15) 0.0360(6) Uani 1 1 d . . .
H11A H 1.2838 0.7801 0.3234 0.043 Uiso 1 1 calc R . .
H11B H 1.1132 0.8674 0.3136 0.043 Uiso 1 1 calc R . .
C12 C 1.0342(3) 0.6987(2) 0.34444(14) 0.0345(6) Uani 1 1 d . . .
H12A H 1.0271 0.7179 0.4045 0.041 Uiso 1 1 calc R . .
H12B H 1.0884 0.6195 0.3390 0.041 Uiso 1 1 calc R . .
C13 C 0.8389(3) 0.69827(19) 0.30715(14) 0.0310(5) Uani 1 1 d . . .
C14 C 0.8569(3) 0.6802(2) 0.21200(14) 0.0318(5) Uani 1 1 d . . .
H14A H 0.9260 0.6052 0.2044 0.038 Uiso 1 1 calc R . .
C15 C 0.6616(3) 0.6559(2) 0.18314(15) 0.0363(6) Uani 1 1 d . . .
H15A H 0.6607 0.6114 0.1301 0.044 Uiso 1 1 calc R . .
H15B H 0.5919 0.7296 0.1756 0.044 Uiso 1 1 calc R . .
C16 C 0.5816(3) 0.5824(2) 0.25483(14) 0.0349(6) Uani 1 1 d . . .
H16A H 0.5671 0.4997 0.2372 0.042 Uiso 1 1 calc R . .
H16B H 0.4597 0.6131 0.2713 0.042 Uiso 1 1 calc R . .
C17 C 0.7183(3) 0.5906(2) 0.32951(14) 0.0311(5) Uani 1 1 d . . .
H17A H 0.7996 0.5201 0.3265 0.037 Uiso 1 1 calc R . .
C18 C 0.7379(3) 0.8120(2) 0.32888(15) 0.0359(5) Uani 1 1 d . . .
H18A H 0.6145 0.8104 0.3044 0.054 Uiso 1 1 calc R . .
H18B H 0.8062 0.8790 0.3065 0.054 Uiso 1 1 calc R . .
H18C H 0.7282 0.8194 0.3896 0.054 Uiso 1 1 calc R . .
C20 C 0.6219(3) 0.5869(2) 0.41474(14) 0.0345(5) Uani 1 1 d . . .
H20A H 0.5368 0.6556 0.4181 0.041 Uiso 1 1 calc R . .
C21 C 0.7575(3) 0.5953(3) 0.48771(14) 0.0440(6) Uani 1 1 d . . .
H21A H 0.8312 0.6667 0.4821 0.066 Uiso 1 1 calc R . .
H21B H 0.8386 0.5267 0.4873 0.066 Uiso 1 1 calc R . .
H21C H 0.6893 0.5977 0.5404 0.066 Uiso 1 1 calc R . .
C22 C 0.5069(3) 0.4751(2) 0.42355(16) 0.0356(6) Uani 1 1 d . . .
H22A H 0.4484 0.4573 0.3693 0.043 Uiso 1 1 calc R . .
H22B H 0.5893 0.4090 0.4376 0.043 Uiso 1 1 calc R . .
C23 C 0.3589(3) 0.4846(2) 0.48982(16) 0.0388(6) Uani 1 1 d . . .
H23A H 0.4154 0.5117 0.5426 0.047 Uiso 1 1 calc R . .
H23B H 0.2679 0.5442 0.4723 0.047 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
C8 O1 1.439(3) . ?
C8 C14 1.510(3) . ?
C8 C9 1.523(3) . ?
C8 H8A 1.0000 . ?
O1 H1A 0.8400 . ?
O2 C23 1.430(3) . ?
O2 H2A 0.8400 . ?
C9 C11 1.532(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 C12 1.522(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.542(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.532(3) . ?
C13 C14 1.546(3) . ?
C13 C17 1.551(3) . ?
C14 C15 1.521(3) . ?
C14 H14A 1.0000 . ?
C15 C16 1.538(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.560(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C20 1.537(3) . ?
C17 H17A 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 C22 1.532(3) . ?
C20 C21 1.534(3) . ?
C20 H20A 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.518(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?

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 C8 C14 111.93(18) . . ?
O1 C8 C9 107.96(19) . . ?
C14 C8 C9 108.50(18) . . ?
O1 C8 H8A 109.5 . . ?
C14 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C8 O1 H1A 109.5 . . ?
C23 O2 H2A 109.5 . . ?
C8 C9 C11 110.54(19) . . ?
C8 C9 H9A 109.5 . . ?
C11 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C11 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C12 C11 C9 113.0(2) . . ?
C12 C11 H11A 109.0 . . ?
C9 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C9 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 111.63(19) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C18 C13 C12 110.58(19) . . ?
C18 C13 C14 112.24(19) . . ?
C12 C13 C14 107.77(19) . . ?
C18 C13 C17 110.26(18) . . ?
C12 C13 C17 115.75(19) . . ?
C14 C13 C17 99.82(17) . . ?
C8 C14 C15 120.24(19) . . ?
C8 C14 C13 113.16(19) . . ?
C15 C14 C13 104.22(19) . . ?
C8 C14 H14A 106.1 . . ?
C15 C14 H14A 106.1 . . ?
C13 C14 H14A 106.1 . . ?
C14 C15 C16 103.05(18) . . ?
C14 C15 H15A 111.2 . . ?
C16 C15 H15A 111.2 . . ?
C14 C15 H15B 111.2 . . ?
C16 C15 H15B 111.2 . . ?
H15A C15 H15B 109.1 . . ?
C15 C16 C17 107.45(18) . . ?
C15 C16 H16A 110.2 . . ?
C17 C16 H16A 110.2 . . ?
C15 C16 H16B 110.2 . . ?
C17 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
C20 C17 C13 119.05(18) . . ?
C20 C17 C16 112.95(18) . . ?
C13 C17 C16 103.36(17) . . ?
C20 C17 H17A 106.9 . . ?
C13 C17 H17A 106.9 . . ?
C16 C17 H17A 106.9 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C22 C20 C21 109.4(2) . . ?
C22 C20 C17 110.75(18) . . ?
C21 C20 C17 112.5(2) . . ?
C22 C20 H20A 108.0 . . ?
C21 C20 H20A 108.0 . . ?
C17 C20 H20A 108.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C20 113.17(19) . . ?
C23 C22 H22A 108.9 . . ?
C20 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C20 C22 H22B 108.9 . . ?
H22A C22 H22B 107.8 . . ?
O2 C23 C22 112.85(19) . . ?
O2 C23 H23A 109.0 . . ?
C22 C23 H23A 109.0 . . ?
O2 C23 H23B 109.0 . . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 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
O1 C8 C9 C11 -178.52(18) . . . . ?
C14 C8 C9 C11 -57.0(3) . . . . ?
C8 C9 C11 C12 55.2(3) . . . . ?
C9 C11 C12 C13 -54.0(3) . . . . ?
C11 C12 C13 C18 -69.5(2) . . . . ?
C11 C12 C13 C14 53.5(2) . . . . ?
C11 C12 C13 C17 164.17(19) . . . . ?
O1 C8 C14 C15 -55.9(3) . . . . ?
C9 C8 C14 C15 -174.9(2) . . . . ?
O1 C8 C14 C13 -179.83(18) . . . . ?
C9 C8 C14 C13 61.1(2) . . . . ?
C18 C13 C14 C8 63.1(2) . . . . ?
C12 C13 C14 C8 -58.9(2) . . . . ?
C17 C13 C14 C8 179.88(18) . . . . ?
C18 C13 C14 C15 -69.2(2) . . . . ?
C12 C13 C14 C15 168.76(18) . . . . ?
C17 C13 C14 C15 47.5(2) . . . . ?
C8 C14 C15 C16 -165.2(2) . . . . ?
C13 C14 C15 C16 -37.1(2) . . . . ?
C14 C15 C16 C17 12.1(2) . . . . ?
C18 C13 C17 C20 -46.3(3) . . . . ?
C12 C13 C17 C20 80.1(3) . . . . ?
C14 C13 C17 C20 -164.55(19) . . . . ?
C18 C13 C17 C16 79.9(2) . . . . ?
C12 C13 C17 C16 -153.7(2) . . . . ?
C14 C13 C17 C16 -38.4(2) . . . . ?
C15 C16 C17 C20 146.91(19) . . . . ?
C15 C16 C17 C13 16.9(2) . . . . ?
C13 C17 C20 C22 178.73(19) . . . . ?
C16 C17 C20 C22 57.2(2) . . . . ?
C13 C17 C20 C21 -58.4(3) . . . . ?
C16 C17 C20 C21 -179.9(2) . . . . ?
C21 C20 C22 C23 75.8(3) . . . . ?
C17 C20 C22 C23 -159.6(2) . . . . ?
C20 C22 C23 O2 -173.22(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
O1 H1A O2 0.84 1.87 2.657(2) 155.8 2_664
O2 H2A O1 0.84 1.93 2.669(2) 146.1 3_645

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.13
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_anc1
_database_code_depnum_ccdc_archive 'CCDC 999113'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H22 O4 S'
_chemical_formula_sum            'C17 H22 O4 S'
_chemical_formula_weight         322.41
_chemical_absolute_configuration ad

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'
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           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   7.4726(4)
_cell_length_b                   13.7659(8)
_cell_length_c                   15.3749(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1581.57(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1953
_cell_measurement_theta_min      3.035
_cell_measurement_theta_max      36.245

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_type   multi-scans
_exptl_absorpt_correction_T_min  0.8884
_exptl_absorpt_correction_T_max  0.9573
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            114970
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         36.36
_reflns_number_total             7697
_reflns_number_gt                7325
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0464P)²+0.1207P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_number_reflns         7697
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0688
_refine_ls_wR_factor_gt          0.0674
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.389996(19) 0.399313(12) 0.076465(10) 0.01041(3) Uani 1 1 d . . .
O1 O 0.45604(7) 0.37731(4) 0.17194(3) 0.01183(9) Uani 1 1 d . . .
O2 O 1.10718(9) 0.29412(5) 0.37380(5) 0.02638(13) Uani 1 1 d . . .
O3 O 0.24140(7) 0.46339(4) 0.08844(4) 0.01648(10) Uani 1 1 d . . .
O4 O 0.36582(8) 0.30957(4) 0.03076(4) 0.01589(10) Uani 1 1 d . . .
C1 C 0.57053(8) 0.46214(5) 0.03041(4) 0.01058(10) Uani 1 1 d . . .
C2 C 0.70663(9) 0.41051(5) -0.01105(5) 0.01242(11) Uani 1 1 d . . .
H2 H 0.6970(18) 0.3402(9) -0.0199(8) 0.017(3) Uiso 1 1 d . . .
C3 C 0.85908(9) 0.46057(6) -0.03773(5) 0.01457(12) Uani 1 1 d . . .
H3 H 0.9530(18) 0.4235(9) -0.0604(8) 0.021(3) Uiso 1 1 d . . .
C4 C 0.87598(9) 0.56070(5) -0.02474(5) 0.01447(11) Uani 1 1 d . . .
C5 C 0.73511(10) 0.61072(5) 0.01448(5) 0.01609(12) Uani 1 1 d . . .
H5 H 0.745(2) 0.6755(10) 0.0236(9) 0.027(3) Uiso 1 1 d . . .
C6 C 0.58271(9) 0.56234(5) 0.04264(5) 0.01415(11) Uani 1 1 d . . .
H6 H 0.4977(16) 0.5974(9) 0.0663(8) 0.016(3) Uiso 1 1 d . . .
C7 C 1.04425(10) 0.61255(7) -0.05074(6) 0.02123(15) Uani 1 1 d . . .
H7A H 1.077(3) 0.5899(14) -0.1048(13) 0.061(6) Uiso 1 1 d . . .
H7B H 1.127(2) 0.6000(10) -0.0103(9) 0.031(4) Uiso 1 1 d . . .
H7C H 1.027(2) 0.6803(12) -0.0599(10) 0.040(4) Uiso 1 1 d . . .
C8 C 0.59641(8) 0.30282(5) 0.18378(4) 0.01051(10) Uani 1 1 d . . .
H8 H 0.6413(15) 0.2884(8) 0.1261(7) 0.008(2) Uiso 1 1 d . . .
C9 C 0.50996(9) 0.21282(5) 0.22371(5) 0.01300(11) Uani 1 1 d . . .
H9A H 0.4457(17) 0.2355(9) 0.2769(8) 0.019(3) Uiso 1 1 d . . .
H9B H 0.4262(17) 0.1886(9) 0.1806(8) 0.015(3) Uiso 1 1 d . . .
C11 C 0.65087(9) 0.13574(5) 0.24653(5) 0.01453(12) Uani 1 1 d . . .
H11A H 0.593(2) 0.0772(11) 0.2776(9) 0.031(4) Uiso 1 1 d . . .
H11B H 0.7019(16) 0.1145(9) 0.1893(8) 0.015(3) Uiso 1 1 d . . .
C12 C 0.80030(9) 0.17651(5) 0.30484(5) 0.01422(11) Uani 1 1 d . . .
H12A H 0.7471(15) 0.1919(8) 0.3618(7) 0.012(2) Uiso 1 1 d . . .
H12B H 0.8968(17) 0.1285(8) 0.3133(8) 0.015(3) Uiso 1 1 d . . .
C13 C 0.88199(9) 0.26608(5) 0.26222(4) 0.01139(10) Uani 1 1 d . . .
C14 C 0.73585(9) 0.34301(5) 0.24504(4) 0.01057(10) Uani 1 1 d . . .
H14 H 0.6777(18) 0.3507(10) 0.3052(8) 0.020(3) Uiso 1 1 d . . .
C15 C 0.84022(10) 0.43625(6) 0.22396(5) 0.01517(12) Uani 1 1 d . . .
H15A H 0.7728(19) 0.4923(10) 0.2340(9) 0.023(3) Uiso 1 1 d . . .
H15B H 0.881(2) 0.4370(10) 0.1646(9) 0.025(3) Uiso 1 1 d . . .
C16 C 0.99579(10) 0.43176(6) 0.29015(5) 0.01650(12) Uani 1 1 d . . .
H16A H 0.968(2) 0.4702(10) 0.3386(9) 0.026(3) Uiso 1 1 d . . .
H16B H 1.108(2) 0.4520(10) 0.2616(9) 0.028(3) Uiso 1 1 d . . .
C17 C 1.01015(9) 0.32576(6) 0.31762(5) 0.01496(12) Uani 1 1 d . . .
C18 C 0.99078(10) 0.23870(6) 0.18053(5) 0.01762(13) Uani 1 1 d . . .
H18A H 1.085(2) 0.1940(11) 0.1974(10) 0.031(4) Uiso 1 1 d . . .
H18B H 0.9164(17) 0.2086(10) 0.1359(8) 0.021(3) Uiso 1 1 d . . .
H18C H 1.040(2) 0.2955(12) 0.1523(11) 0.038(4) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4300(5) . ?
S1 O4 1.4327(6) . ?
S1 O1 1.5780(5) . ?
S1 C1 1.7520(7) . ?
O1 C8 1.4781(8) . ?
O2 C17 1.2089(9) . ?
C1 C2 1.3950(9) . ?
C1 C6 1.3951(10) . ?
C2 C3 1.3931(10) . ?
C2 H2 0.980(12) . ?
C3 C4 1.3985(11) . ?
C3 H3 0.935(14) . ?
C4 C5 1.3950(11) . ?
C4 C7 1.5001(10) . ?
C5 C6 1.3885(10) . ?
C5 H5 0.905(14) . ?
C6 H6 0.877(12) . ?
C7 H7A 0.92(2) . ?
C7 H7B 0.892(15) . ?
C7 H7C 0.952(16) . ?
C8 C14 1.5096(9) . ?
C8 C9 1.5262(10) . ?
C8 H8 0.968(11) . ?
C9 C11 1.5355(10) . ?
C9 H9A 0.999(12) . ?
C9 H9B 0.971(12) . ?
C11 C12 1.5381(10) . ?
C11 H11A 1.031(15) . ?
C11 H11B 1.002(12) . ?
C12 C13 1.5239(10) . ?
C12 H12A 0.985(12) . ?
C12 H12B 0.987(12) . ?
C13 C17 1.5223(10) . ?
C13 C18 1.5429(10) . ?
C13 C14 1.5440(9) . ?
C14 C15 1.5364(10) . ?
C14 H14 1.027(12) . ?
C15 C16 1.5463(11) . ?
C15 H15A 0.934(13) . ?
C15 H15B 0.961(14) . ?
C16 C17 1.5229(11) . ?
C16 H16A 0.937(14) . ?
C16 H16B 0.987(15) . ?
C18 H18A 0.970(15) . ?
C18 H18B 0.976(13) . ?
C18 H18C 0.966(16) . ?

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 O4 119.81(3) . . ?
O3 S1 O1 103.97(3) . . ?
O4 S1 O1 109.28(3) . . ?
O3 S1 C1 110.21(3) . . ?
O4 S1 C1 108.93(3) . . ?
O1 S1 C1 103.30(3) . . ?
C8 O1 S1 118.01(4) . . ?
C2 C1 C6 121.18(6) . . ?
C2 C1 S1 119.65(5) . . ?
C6 C1 S1 118.94(5) . . ?
C3 C2 C1 118.60(6) . . ?
C3 C2 H2 120.5(8) . . ?
C1 C2 H2 120.9(8) . . ?
C2 C3 C4 121.29(7) . . ?
C2 C3 H3 117.0(8) . . ?
C4 C3 H3 121.6(8) . . ?
C5 C4 C3 118.69(6) . . ?
C5 C4 C7 120.85(7) . . ?
C3 C4 C7 120.44(7) . . ?
C6 C5 C4 121.13(7) . . ?
C6 C5 H5 119.4(9) . . ?
C4 C5 H5 119.4(9) . . ?
C5 C6 C1 119.06(7) . . ?
C5 C6 H6 117.4(8) . . ?
C1 C6 H6 123.5(8) . . ?
C4 C7 H7A 107.5(13) . . ?
C4 C7 H7B 107.5(10) . . ?
H7A C7 H7B 112.5(16) . . ?
C4 C7 H7C 113.0(11) . . ?
H7A C7 H7C 103.5(15) . . ?
H7B C7 H7C 112.8(14) . . ?
O1 C8 C14 108.21(5) . . ?
O1 C8 C9 108.19(5) . . ?
C14 C8 C9 109.80(5) . . ?
O1 C8 H8 106.0(7) . . ?
C14 C8 H8 114.0(7) . . ?
C9 C8 H8 110.4(7) . . ?
C8 C9 C11 111.26(5) . . ?
C8 C9 H9A 106.2(7) . . ?
C11 C9 H9A 111.0(7) . . ?
C8 C9 H9B 106.1(7) . . ?
C11 C9 H9B 111.2(7) . . ?
H9A C9 H9B 110.9(10) . . ?
C9 C11 C12 112.26(6) . . ?
C9 C11 H11A 111.0(9) . . ?
C12 C11 H11A 108.6(8) . . ?
C9 C11 H11B 105.2(7) . . ?
C12 C11 H11B 110.0(7) . . ?
H11A C11 H11B 109.8(10) . . ?
C13 C12 C11 109.60(6) . . ?
C13 C12 H12A 111.8(7) . . ?
C11 C12 H12A 107.7(6) . . ?
C13 C12 H12B 107.8(7) . . ?
C11 C12 H12B 111.3(7) . . ?
H12A C12 H12B 108.7(9) . . ?
C17 C13 C12 116.62(6) . . ?
C17 C13 C18 104.82(6) . . ?
C12 C13 C18 111.31(6) . . ?
C17 C13 C14 99.82(5) . . ?
C12 C13 C14 110.20(5) . . ?
C18 C13 C14 113.64(6) . . ?
C8 C14 C15 121.66(6) . . ?
C8 C14 C13 110.10(5) . . ?
C15 C14 C13 104.48(5) . . ?
C8 C14 H14 107.9(7) . . ?
C15 C14 H14 108.6(7) . . ?
C13 C14 H14 102.5(7) . . ?
C14 C15 C16 102.09(6) . . ?
C14 C15 H15A 112.4(8) . . ?
C16 C15 H15A 109.2(9) . . ?
C14 C15 H15B 111.6(8) . . ?
C16 C15 H15B 112.8(9) . . ?
H15A C15 H15B 108.5(11) . . ?
C17 C16 C15 105.89(6) . . ?
C17 C16 H16A 109.6(9) . . ?
C15 C16 H16A 109.7(9) . . ?
C17 C16 H16B 109.5(9) . . ?
C15 C16 H16B 109.6(8) . . ?
H16A C16 H16B 112.3(12) . . ?
O2 C17 C13 125.64(7) . . ?
O2 C17 C16 125.84(7) . . ?
C13 C17 C16 108.52(6) . . ?
C13 C18 H18A 108.6(9) . . ?
C13 C18 H18B 112.1(8) . . ?
H18A C18 H18B 109.4(11) . . ?
C13 C18 H18C 111.6(10) . . ?
H18A C18 H18C 111.0(13) . . ?
H18B C18 H18C 104.1(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
O3 S1 O1 C8 172.65(5) . . . . ?
O4 S1 O1 C8 43.61(5) . . . . ?
C1 S1 O1 C8 -72.23(5) . . . . ?
O3 S1 C1 C2 -160.41(6) . . . . ?
O4 S1 C1 C2 -27.07(7) . . . . ?
O1 S1 C1 C2 89.02(6) . . . . ?
O3 S1 C1 C6 25.10(7) . . . . ?
O4 S1 C1 C6 158.44(6) . . . . ?
O1 S1 C1 C6 -85.47(6) . . . . ?
C6 C1 C2 C3 2.13(11) . . . . ?
S1 C1 C2 C3 -172.23(5) . . . . ?
C1 C2 C3 C4 -0.90(11) . . . . ?
C2 C3 C4 C5 -1.07(11) . . . . ?
C2 C3 C4 C7 177.56(7) . . . . ?
C3 C4 C5 C6 1.88(11) . . . . ?
C7 C4 C5 C6 -176.74(7) . . . . ?
C4 C5 C6 C1 -0.70(11) . . . . ?
C2 C1 C6 C5 -1.35(11) . . . . ?
S1 C1 C6 C5 173.05(6) . . . . ?
S1 O1 C8 C14 133.67(5) . . . . ?
S1 O1 C8 C9 -107.42(5) . . . . ?
O1 C8 C9 C11 -174.28(5) . . . . ?
C14 C8 C9 C11 -56.39(8) . . . . ?
C8 C9 C11 C12 54.04(8) . . . . ?
C9 C11 C12 C13 -54.22(8) . . . . ?
C11 C12 C13 C17 170.03(6) . . . . ?
C11 C12 C13 C18 -69.80(7) . . . . ?
C11 C12 C13 C14 57.22(7) . . . . ?
O1 C8 C14 C15 -59.60(8) . . . . ?
C9 C8 C14 C15 -177.48(6) . . . . ?
O1 C8 C14 C13 177.82(5) . . . . ?
C9 C8 C14 C13 59.94(7) . . . . ?
C17 C13 C14 C8 175.46(5) . . . . ?
C12 C13 C14 C8 -61.29(7) . . . . ?
C18 C13 C14 C8 64.42(7) . . . . ?
C17 C13 C14 C15 43.26(7) . . . . ?
C12 C13 C14 C15 166.50(6) . . . . ?
C18 C13 C14 C15 -67.78(7) . . . . ?
C8 C14 C15 C16 -165.29(6) . . . . ?
C13 C14 C15 C16 -40.10(7) . . . . ?
C14 C15 C16 C17 20.57(8) . . . . ?
C12 C13 C17 O2 31.49(11) . . . . ?
C18 C13 C17 O2 -92.09(10) . . . . ?
C14 C13 C17 O2 150.10(8) . . . . ?
C12 C13 C17 C16 -148.66(6) . . . . ?
C18 C13 C17 C16 87.76(7) . . . . ?
C14 C13 C17 C16 -30.05(7) . . . . ?
C15 C16 C17 O2 -173.91(8) . . . . ?
C15 C16 C17 C13 6.24(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        36.36
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.050
