# Electronic Supplementary Material (ESI) for MedChemComm.
# 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_ww
_database_code_depnum_ccdc_archive 'CCDC 1526177'
_audit_update_record             
;
2017-01-09 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H45 N O5 S'
_chemical_formula_weight         555.75

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.9676(16)
_cell_length_b                   16.491(4)
_cell_length_c                   16.558(5)
_cell_angle_alpha                97.004(4)
_cell_angle_beta                 93.026(4)
_cell_angle_gamma                92.510(3)
_cell_volume                     1613.0(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2930
_cell_measurement_theta_min      2.4829
_cell_measurement_theta_max      25.7140

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9703
_exptl_absorpt_correction_T_max  0.9730
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  bruker-CCD
_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            13089
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         25.10
_reflns_number_total             5704
_reflns_number_gt                3487
_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)+(0.0561P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5704
_refine_ls_number_parameters     362
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.085
_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 0.71137(10) 0.94039(3) 0.08790(4) 0.0523(2) Uani 1 1 d . A .
N1 N 1.5220(3) 1.67749(10) 0.18828(11) 0.0508(5) Uani 1 1 d . . .
O1 O 1.6757(3) 1.73432(10) 0.19813(11) 0.0814(6) Uani 1 1 d . . .
O2 O 1.0890(3) 1.47037(8) 0.15220(11) 0.0632(5) Uani 1 1 d . A .
O3 O 0.7887(4) 1.49372(13) 0.2244(3) 0.0888(17) Uani 0.874(10) 1 d PDU A 1
O3A O 0.757(2) 1.4909(9) 0.1592(17) 0.064(7) Uani 0.126(10) 1 d PDU A 2
O4 O 0.7547(3) 0.89765(9) 0.00987(10) 0.0704(5) Uani 1 1 d . . .
O5 O 0.4879(2) 0.93477(9) 0.11508(10) 0.0617(5) Uani 1 1 d . . .
C1 C 1.4206(4) 1.65559(14) 0.10404(14) 0.0547(6) Uani 1 1 d . . .
C2 C 1.3091(4) 1.57004(13) 0.09784(14) 0.0592(7) Uani 1 1 d . . .
H2A H 1.2193 1.5594 0.0468 0.071 Uiso 1 1 calc R . .
H2B H 1.4252 1.5306 0.0964 0.071 Uiso 1 1 calc R . .
C3 C 1.1621(4) 1.55686(12) 0.16617(15) 0.0502(6) Uani 1 1 d . . .
H3A H 1.0325 1.5913 0.1651 0.060 Uiso 1 1 calc R . .
C4 C 1.2942(4) 1.57425(13) 0.24631(14) 0.0527(6) Uani 1 1 d . . .
H4A H 1.4093 1.5347 0.2483 0.063 Uiso 1 1 calc R . .
H4B H 1.1948 1.5669 0.2896 0.063 Uiso 1 1 calc R . .
C5 C 1.4062(4) 1.66020(13) 0.26223(14) 0.0547(6) Uani 1 1 d . . .
C6 C 1.6098(5) 1.65505(18) 0.04538(16) 0.0816(8) Uani 1 1 d . . .
H6A H 1.7149 1.6153 0.0578 0.122 Uiso 1 1 calc R . .
H6B H 1.6853 1.7082 0.0510 0.122 Uiso 1 1 calc R . .
H6C H 1.5481 1.6413 -0.0096 0.122 Uiso 1 1 calc R . .
C7 C 1.2527(5) 1.71931(16) 0.08395(18) 0.0811(9) Uani 1 1 d . . .
H7A H 1.1338 1.7199 0.1209 0.122 Uiso 1 1 calc R . .
H7B H 1.1908 1.7054 0.0290 0.122 Uiso 1 1 calc R . .
H7C H 1.3284 1.7724 0.0894 0.122 Uiso 1 1 calc R . .
C8 C 1.2348(4) 1.72480(15) 0.28455(19) 0.0849(9) Uani 1 1 d . . .
H8A H 1.1207 1.7226 0.2411 0.127 Uiso 1 1 calc R . .
H8B H 1.3096 1.7782 0.2928 0.127 Uiso 1 1 calc R . .
H8C H 1.1670 1.7141 0.3337 0.127 Uiso 1 1 calc R . .
C9 C 1.5856(5) 1.66384(18) 0.33175(16) 0.0837(9) Uani 1 1 d . . .
H9A H 1.6925 1.6232 0.3184 0.125 Uiso 1 1 calc R . .
H9B H 1.5163 1.6536 0.3808 0.125 Uiso 1 1 calc R . .
H9C H 1.6610 1.7171 0.3399 0.125 Uiso 1 1 calc R . .
C10 C 0.8996(4) 1.44697(14) 0.18229(17) 0.0605(7) Uani 1 1 d D . .
C11 C 0.8504(4) 1.35703(12) 0.16670(14) 0.0495(6) Uani 1 1 d . A .
C12 C 0.9979(4) 1.30400(13) 0.13104(14) 0.0514(6) Uani 1 1 d . . .
H12A H 1.1352 1.3243 0.1158 0.062 Uiso 1 1 calc R A .
C13 C 0.9454(4) 1.22151(13) 0.11758(14) 0.0531(6) Uani 1 1 d . A .
H13A H 1.0477 1.1866 0.0934 0.064 Uiso 1 1 calc R . .
C14 C 0.7418(4) 1.18937(12) 0.13962(13) 0.0474(6) Uani 1 1 d . . .
C15 C 0.5962(4) 1.24277(14) 0.17647(18) 0.0718(8) Uani 1 1 d . A .
H15A H 0.4599 1.2226 0.1926 0.086 Uiso 1 1 calc R . .
C16 C 0.6490(4) 1.32566(14) 0.18983(19) 0.0766(8) Uani 1 1 d . . .
H16A H 0.5481 1.3607 0.2146 0.092 Uiso 1 1 calc R A .
C17 C 0.6818(4) 1.10136(13) 0.12712(14) 0.0518(6) Uani 1 1 d . A .
H17A H 0.5470 1.0849 0.1474 0.062 Uiso 1 1 calc R . .
C18 C 0.7961(4) 1.04394(13) 0.09084(14) 0.0522(6) Uani 1 1 d . . .
H18A H 0.9257 1.0580 0.0659 0.063 Uiso 1 1 calc R A .
C19 C 0.9018(4) 0.90643(13) 0.16179(15) 0.0610(7) Uani 1 1 d . . .
H19A H 0.8594 0.8505 0.1691 0.073 Uiso 1 1 calc R A .
H19B H 1.0521 0.9073 0.1421 0.073 Uiso 1 1 calc R . .
C20 C 0.9029(4) 0.95908(14) 0.24190(15) 0.0540(6) Uani 1 1 d . A .
C21 C 0.7251(4) 0.95605(16) 0.29143(16) 0.0735(8) Uani 1 1 d . . .
H21A H 0.6108 0.9157 0.2783 0.088 Uiso 1 1 calc R A .
C22 C 0.7137(4) 1.01142(18) 0.35960(17) 0.0783(8) Uani 1 1 d . A .
H22A H 0.5890 1.0082 0.3907 0.094 Uiso 1 1 calc R . .
C23 C 0.8784(4) 1.07150(15) 0.38412(15) 0.0624(7) Uani 1 1 d . . .
C24 C 1.0607(4) 1.07224(17) 0.33528(17) 0.0736(8) Uani 1 1 d . A .
H24A H 1.1781 1.1112 0.3496 0.088 Uiso 1 1 calc R . .
C25 C 1.0727(4) 1.01728(16) 0.26659(17) 0.0696(7) Uani 1 1 d . . .
H25A H 1.1987 1.0194 0.2360 0.084 Uiso 1 1 calc R A .
C26 C 0.8550(5) 1.13579(19) 0.45728(18) 0.0782(8) Uani 1 1 d . A .
C27 C 0.7234(7) 1.0998(2) 0.5233(2) 0.1303(14) Uani 1 1 d . . .
H27A H 0.8068 1.0577 0.5442 0.195 Uiso 1 1 calc R A .
H27B H 0.5802 1.0771 0.5000 0.195 Uiso 1 1 calc R . .
H27C H 0.7013 1.1423 0.5668 0.195 Uiso 1 1 calc R . .
C28 C 0.7197(6) 1.2035(2) 0.4284(2) 0.1210(13) Uani 1 1 d . . .
H28A H 0.7989 1.2283 0.3880 0.181 Uiso 1 1 calc R A .
H28B H 0.6986 1.2441 0.4738 0.181 Uiso 1 1 calc R . .
H28C H 0.5761 1.1812 0.4052 0.181 Uiso 1 1 calc R . .
C29 C 1.0798(5) 1.1701(3) 0.4955(2) 0.1490(18) Uani 1 1 d . . .
H29A H 1.1634 1.1939 0.4556 0.223 Uiso 1 1 calc R A .
H29B H 1.1618 1.1269 0.5151 0.223 Uiso 1 1 calc R . .
H29C H 1.0571 1.2112 0.5402 0.223 Uiso 1 1 calc R . .
C30 C 1.2710(14) 1.3846(5) 0.3811(5) 0.280(4) Uani 1 1 d . B .
H30A H 1.2427 1.3266 0.3688 0.420 Uiso 1 1 calc R . .
H30B H 1.4198 1.3959 0.4060 0.420 Uiso 1 1 calc R . .
H30C H 1.2580 1.4095 0.3317 0.420 Uiso 1 1 calc R . .
C31 C 1.112(2) 1.4171(7) 0.4355(7) 0.345(6) Uani 1 1 d DU . .
H31A H 0.9788 1.4297 0.4042 0.413 Uiso 0.874(10) 1 calc PR A 1
H31B H 1.0679 1.3758 0.4694 0.413 Uiso 0.874(10) 1 calc PR A 1
H31C H 0.9702 1.3884 0.4161 0.413 Uiso 0.126(10) 1 d PR A 2
H31D H 1.1556 1.3943 0.4850 0.413 Uiso 0.126(10) 1 d PR A 2
C32 C 1.192(6) 1.4857(12) 0.4842(12) 0.291(11) Uiso 0.51(2) 1 d PDU B 1
H32D H 1.3232 1.4736 0.5159 0.436 Uiso 0.51(2) 1 d PR B 1
H32B H 1.2319 1.5267 0.4502 0.436 Uiso 0.51(2) 1 d PR B 1
C32A C 1.048(4) 1.4913(10) 0.4675(10) 0.212(9) Uiso 0.49(2) 1 d PDU . 2
H32C H 0.9272 1.4846 0.5028 0.319 Uiso 0.49(2) 1 d PR B 2
H32F H 0.9988 1.5223 0.4250 0.319 Uiso 0.49(2) 1 d PR B 2


_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 O5 1.4327(16) . ?
S1 O4 1.4360(16) . ?
S1 C18 1.754(2) . ?
S1 C19 1.783(3) . ?
N1 O1 1.272(2) . ?
N1 C1 1.487(3) . ?
N1 C5 1.489(3) . ?
O2 C10 1.320(3) . ?
O2 C3 1.460(2) . ?
O3 C10 1.217(3) . ?
O3A C10 1.216(9) . ?
C1 C2 1.523(3) . ?
C1 C6 1.527(3) . ?
C1 C7 1.537(3) . ?
C2 C3 1.498(3) . ?
C3 C4 1.497(3) . ?
C4 C5 1.527(3) . ?
C5 C9 1.524(3) . ?
C5 C8 1.535(3) . ?
C10 C11 1.488(3) . ?
C11 C12 1.373(3) . ?
C11 C16 1.378(3) . ?
C12 C13 1.371(3) . ?
C13 C14 1.389(3) . ?
C14 C15 1.376(3) . ?
C14 C17 1.467(3) . ?
C15 C16 1.378(3) . ?
C17 C18 1.298(3) . ?
C19 C20 1.494(3) . ?
C20 C25 1.375(3) . ?
C20 C21 1.378(3) . ?
C21 C22 1.369(3) . ?
C22 C23 1.374(3) . ?
C23 C24 1.390(3) . ?
C23 C26 1.526(4) . ?
C24 C25 1.372(3) . ?
C26 C29 1.509(4) . ?
C26 C28 1.516(4) . ?
C26 C27 1.540(4) . ?
C30 C31 1.420(11) . ?
C31 C32A 1.353(9) . ?
C31 C32 1.361(10) . ?
C32A C32A 1.25(3) 2_786 ?

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
O5 S1 O4 118.25(10) . . ?
O5 S1 C18 108.83(10) . . ?
O4 S1 C18 109.30(11) . . ?
O5 S1 C19 109.15(11) . . ?
O4 S1 C19 107.58(11) . . ?
C18 S1 C19 102.59(11) . . ?
O1 N1 C1 116.44(18) . . ?
O1 N1 C5 116.66(18) . . ?
C1 N1 C5 123.18(17) . . ?
C10 O2 C3 118.63(17) . . ?
N1 C1 C2 108.30(18) . . ?
N1 C1 C6 107.97(19) . . ?
C2 C1 C6 109.2(2) . . ?
N1 C1 C7 110.03(19) . . ?
C2 C1 C7 111.9(2) . . ?
C6 C1 C7 109.3(2) . . ?
C3 C2 C1 114.35(19) . . ?
O2 C3 C4 109.41(18) . . ?
O2 C3 C2 105.32(17) . . ?
C4 C3 C2 110.22(18) . . ?
C3 C4 C5 113.99(18) . . ?
N1 C5 C9 107.21(19) . . ?
N1 C5 C4 108.68(17) . . ?
C9 C5 C4 109.6(2) . . ?
N1 C5 C8 110.7(2) . . ?
C9 C5 C8 109.1(2) . . ?
C4 C5 C8 111.51(19) . . ?
O3A C10 O3 52.8(12) . . ?
O3A C10 O2 106.2(9) . . ?
O3 C10 O2 122.8(2) . . ?
O3A C10 C11 117.5(8) . . ?
O3 C10 C11 123.9(2) . . ?
O2 C10 C11 113.0(2) . . ?
C12 C11 C16 118.7(2) . . ?
C12 C11 C10 122.7(2) . . ?
C16 C11 C10 118.5(2) . . ?
C13 C12 C11 120.8(2) . . ?
C12 C13 C14 120.9(2) . . ?
C15 C14 C13 117.9(2) . . ?
C15 C14 C17 119.8(2) . . ?
C13 C14 C17 122.3(2) . . ?
C14 C15 C16 121.1(2) . . ?
C15 C16 C11 120.5(2) . . ?
C18 C17 C14 127.1(2) . . ?
C17 C18 S1 121.42(18) . . ?
C20 C19 S1 111.64(16) . . ?
C25 C20 C21 116.8(2) . . ?
C25 C20 C19 121.5(2) . . ?
C21 C20 C19 121.4(2) . . ?
C22 C21 C20 121.2(2) . . ?
C21 C22 C23 122.9(3) . . ?
C22 C23 C24 115.5(2) . . ?
C22 C23 C26 121.9(2) . . ?
C24 C23 C26 122.6(2) . . ?
C25 C24 C23 122.0(2) . . ?
C24 C25 C20 121.6(2) . . ?
C29 C26 C28 110.3(3) . . ?
C29 C26 C23 112.3(2) . . ?
C28 C26 C23 107.8(2) . . ?
C29 C26 C27 108.1(3) . . ?
C28 C26 C27 107.2(3) . . ?
C23 C26 C27 111.0(3) . . ?
C32A C31 C32 38.9(12) . . ?
C32A C31 C30 138.2(12) . . ?
C32 C31 C30 112.9(16) . . ?
C32A C32A C31 128(2) 2_786 . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_ww
_database_code_depnum_ccdc_archive 'CCDC 1526188'
_audit_update_record             
;
2017-01-09 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H29 Cl N O5 S'
_chemical_formula_weight         491.00

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   23.6905(18)
_cell_length_b                   12.9222(10)
_cell_length_c                   8.2629(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.980(2)
_cell_angle_gamma                90.00
_cell_volume                     2526.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3394
_cell_measurement_theta_min      2.9289
_cell_measurement_theta_max      24.7440

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1036
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9432
_exptl_absorpt_correction_T_max  0.9482
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  bruker-CCD
_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            12823
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         0.86
_diffrn_reflns_theta_max         25.10
_reflns_number_total             4493
_reflns_number_gt                3412
_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)+(0.1065P)²+0.1224P] 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_number_reflns         4493
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1685
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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 0.47722(2) 0.91310(4) 0.25300(7) 0.0373(2) Uani 1 1 d . . .
Cl1 Cl 0.24577(4) 0.58315(9) 0.20476(15) 0.1051(4) Uani 1 1 d . . .
O1 O 0.49280(7) 0.83406(12) 0.3690(2) 0.0483(4) Uani 1 1 d . . .
N1 N 0.06818(10) 1.49205(19) 0.7445(3) 0.0641(7) Uani 1 1 d . . .
C1 C 0.30364(12) 0.6612(2) 0.1702(4) 0.0588(7) Uani 1 1 d . . .
O2 O 0.52094(7) 0.98039(13) 0.2011(2) 0.0501(5) Uani 1 1 d . . .
C2 C 0.35703(12) 0.6220(2) 0.1908(3) 0.0513(7) Uani 1 1 d . . .
H2A H 0.3625 0.5539 0.2245 0.062 Uiso 1 1 calc R . .
O3 O 0.27683(8) 1.46256(13) 0.5993(3) 0.0655(6) Uani 1 1 d . . .
C3 C 0.40271(10) 0.68374(17) 0.1613(3) 0.0408(6) Uani 1 1 d . . .
H3A H 0.4390 0.6566 0.1739 0.049 Uiso 1 1 calc R . .
O4 O 0.21409(7) 1.33411(12) 0.6171(2) 0.0533(5) Uani 1 1 d . . .
C4 C 0.39531(10) 0.78536(17) 0.1134(3) 0.0382(5) Uani 1 1 d . . .
C5 C 0.34108(12) 0.8242(2) 0.0950(4) 0.0563(7) Uani 1 1 d . . .
H5A H 0.3356 0.8926 0.0633 0.068 Uiso 1 1 calc R . .
O5 O 0.02418(9) 1.5417(2) 0.7862(3) 0.0942(8) Uani 1 1 d . . .
C6 C 0.29505(12) 0.7630(3) 0.1231(4) 0.0679(8) Uani 1 1 d . . .
H6A H 0.2586 0.7897 0.1104 0.082 Uiso 1 1 calc R . .
C7 C 0.44507(10) 0.85233(18) 0.0785(3) 0.0423(6) Uani 1 1 d . . .
H7A H 0.4328 0.9054 0.0014 0.051 Uiso 1 1 calc R . .
H7B H 0.4731 0.8102 0.0281 0.051 Uiso 1 1 calc R . .
C8 C 0.42255(11) 0.98658(18) 0.3310(3) 0.0447(6) Uani 1 1 d . . .
H8A H 0.3937 0.9527 0.3818 0.054 Uiso 1 1 calc R . .
C9 C 0.42118(10) 1.08713(19) 0.3198(3) 0.0452(6) Uani 1 1 d . . .
H9A H 0.4500 1.1181 0.2647 0.054 Uiso 1 1 calc R . .
C10 C 0.37890(10) 1.15670(18) 0.3852(3) 0.0416(6) Uani 1 1 d . . .
C11 C 0.38754(11) 1.26198(19) 0.3764(3) 0.0486(6) Uani 1 1 d . . .
H11A H 0.4193 1.2869 0.3272 0.058 Uiso 1 1 calc R . .
C12 C 0.35037(10) 1.33064(19) 0.4387(3) 0.0477(6) Uani 1 1 d . . .
H12A H 0.3577 1.4013 0.4342 0.057 Uiso 1 1 calc R . .
C13 C 0.30176(9) 1.29556(17) 0.5086(3) 0.0410(6) Uani 1 1 d . . .
C14 C 0.29149(11) 1.18936(18) 0.5141(3) 0.0465(6) Uani 1 1 d . . .
H14A H 0.2588 1.1648 0.5587 0.056 Uiso 1 1 calc R . .
C15 C 0.32950(11) 1.12107(19) 0.4539(3) 0.0471(6) Uani 1 1 d . . .
H15A H 0.3225 1.0504 0.4588 0.056 Uiso 1 1 calc R . .
C16 C 0.26429(10) 1.37318(19) 0.5781(3) 0.0468(6) Uani 1 1 d . . .
C17 C 0.17594(11) 1.40659(19) 0.6913(4) 0.0503(7) Uani 1 1 d . . .
H17A H 0.1967 1.4487 0.7730 0.060 Uiso 1 1 calc R . .
C18 C 0.13198(12) 1.3416(2) 0.7698(4) 0.0573(7) Uani 1 1 d . . .
H18A H 0.1508 1.2967 0.8496 0.069 Uiso 1 1 calc R . .
H18B H 0.1133 1.2980 0.6878 0.069 Uiso 1 1 calc R . .
C19 C 0.08731(12) 1.4048(2) 0.8523(4) 0.0592(7) Uani 1 1 d . . .
C20 C 0.10511(12) 1.5504(2) 0.6337(4) 0.0674(9) Uani 1 1 d . . .
C21 C 0.14722(12) 1.4751(2) 0.5640(4) 0.0616(8) Uani 1 1 d . . .
H21A H 0.1275 1.4320 0.4833 0.074 Uiso 1 1 calc R . .
H21B H 0.1757 1.5142 0.5102 0.074 Uiso 1 1 calc R . .
C22 C 0.03634(13) 1.3360(3) 0.8795(5) 0.0810(10) Uani 1 1 d . . .
H22A H 0.0215 1.3098 0.7773 0.121 Uiso 1 1 calc R . .
H22B H 0.0078 1.3758 0.9295 0.121 Uiso 1 1 calc R . .
H22C H 0.0477 1.2793 0.9488 0.121 Uiso 1 1 calc R . .
C23 C 0.11072(15) 1.4481(3) 1.0172(4) 0.0836(10) Uani 1 1 d . . .
H23A H 0.1429 1.4912 1.0004 0.125 Uiso 1 1 calc R . .
H23B H 0.1218 1.3918 1.0876 0.125 Uiso 1 1 calc R . .
H23C H 0.0820 1.4882 1.0657 0.125 Uiso 1 1 calc R . .
C24 C 0.13489(17) 1.6383(3) 0.7290(7) 0.1034(14) Uani 1 1 d . . .
H24A H 0.1585 1.6098 0.8158 0.155 Uiso 1 1 calc R . .
H24B H 0.1071 1.6831 0.7727 0.155 Uiso 1 1 calc R . .
H24C H 0.1577 1.6772 0.6580 0.155 Uiso 1 1 calc R . .
C25 C 0.06761(15) 1.5949(3) 0.4961(6) 0.1011(14) Uani 1 1 d . . .
H25A H 0.0487 1.5395 0.4378 0.152 Uiso 1 1 calc R . .
H25B H 0.0904 1.6330 0.4240 0.152 Uiso 1 1 calc R . .
H25C H 0.0401 1.6401 0.5395 0.152 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 O2 1.4349(16) . ?
S1 O1 1.4357(17) . ?
S1 C8 1.755(2) . ?
S1 C7 1.778(2) . ?
Cl1 C1 1.738(3) . ?
N1 O5 1.286(3) . ?
N1 C19 1.493(4) . ?
N1 C20 1.502(4) . ?
C1 C2 1.365(4) . ?
C1 C6 1.383(4) . ?
C2 C3 1.377(3) . ?
O3 C16 1.203(3) . ?
C3 C4 1.380(3) . ?
O4 C16 1.346(3) . ?
O4 C17 1.459(3) . ?
C4 C5 1.380(3) . ?
C4 C7 1.502(3) . ?
C5 C6 1.376(4) . ?
C8 C9 1.303(3) . ?
C9 C10 1.469(3) . ?
C10 C11 1.378(3) . ?
C10 C15 1.405(3) . ?
C11 C12 1.369(3) . ?
C12 C13 1.391(3) . ?
C13 C14 1.395(3) . ?
C13 C16 1.475(3) . ?
C14 C15 1.372(3) . ?
C17 C21 1.509(4) . ?
C17 C18 1.510(4) . ?
C18 C19 1.525(4) . ?
C19 C22 1.525(4) . ?
C19 C23 1.549(5) . ?
C20 C25 1.519(5) . ?
C20 C21 1.528(4) . ?
C20 C24 1.533(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 117.80(11) . . ?
O2 S1 C8 109.86(11) . . ?
O1 S1 C8 107.99(11) . . ?
O2 S1 C7 108.09(11) . . ?
O1 S1 C7 108.15(11) . . ?
C8 S1 C7 104.08(12) . . ?
O5 N1 C19 116.2(2) . . ?
O5 N1 C20 114.8(2) . . ?
C19 N1 C20 125.1(2) . . ?
C2 C1 C6 120.7(3) . . ?
C2 C1 Cl1 119.8(2) . . ?
C6 C1 Cl1 119.5(2) . . ?
C1 C2 C3 119.6(2) . . ?
C2 C3 C4 120.9(2) . . ?
C16 O4 C17 115.73(19) . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 C7 120.9(2) . . ?
C5 C4 C7 120.3(2) . . ?
C6 C5 C4 120.9(2) . . ?
C5 C6 C1 119.2(3) . . ?
C4 C7 S1 113.97(16) . . ?
C9 C8 S1 122.0(2) . . ?
C8 C9 C10 126.8(2) . . ?
C11 C10 C15 118.3(2) . . ?
C11 C10 C9 118.6(2) . . ?
C15 C10 C9 123.1(2) . . ?
C12 C11 C10 121.3(2) . . ?
C11 C12 C13 120.5(2) . . ?
C12 C13 C14 118.9(2) . . ?
C12 C13 C16 117.9(2) . . ?
C14 C13 C16 123.1(2) . . ?
C15 C14 C13 120.1(2) . . ?
C14 C15 C10 120.8(2) . . ?
O3 C16 O4 122.7(2) . . ?
O3 C16 C13 124.1(2) . . ?
O4 C16 C13 113.3(2) . . ?
O4 C17 C21 110.5(2) . . ?
O4 C17 C18 106.3(2) . . ?
C21 C17 C18 109.2(2) . . ?
C17 C18 C19 113.9(2) . . ?
N1 C19 C22 108.0(2) . . ?
N1 C19 C18 109.5(2) . . ?
C22 C19 C18 109.1(2) . . ?
N1 C19 C23 109.6(3) . . ?
C22 C19 C23 109.3(3) . . ?
C18 C19 C23 111.2(3) . . ?
N1 C20 C25 108.1(2) . . ?
N1 C20 C21 108.8(2) . . ?
C25 C20 C21 109.1(3) . . ?
N1 C20 C24 109.0(3) . . ?
C25 C20 C24 109.9(3) . . ?
C21 C20 C24 111.9(3) . . ?
C17 C21 C20 113.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.3(4) . . . . ?
Cl1 C1 C2 C3 179.2(2) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C2 C3 C4 C7 -179.0(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C7 C4 C5 C6 178.5(3) . . . . ?
C4 C5 C6 C1 0.0(5) . . . . ?
C2 C1 C6 C5 0.8(5) . . . . ?
Cl1 C1 C6 C5 -179.7(2) . . . . ?
C3 C4 C7 S1 -85.3(2) . . . . ?
C5 C4 C7 S1 95.9(3) . . . . ?
O2 S1 C7 C4 -175.59(16) . . . . ?
O1 S1 C7 C4 55.85(19) . . . . ?
C8 S1 C7 C4 -58.8(2) . . . . ?
O2 S1 C8 C9 8.1(3) . . . . ?
O1 S1 C8 C9 137.8(2) . . . . ?
C7 S1 C8 C9 -107.4(2) . . . . ?
S1 C8 C9 C10 -177.7(2) . . . . ?
C8 C9 C10 C11 173.2(3) . . . . ?
C8 C9 C10 C15 -7.8(4) . . . . ?
C15 C10 C11 C12 2.6(4) . . . . ?
C9 C10 C11 C12 -178.4(2) . . . . ?
C10 C11 C12 C13 -1.9(4) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C11 C12 C13 C16 178.1(2) . . . . ?
C12 C13 C14 C15 1.2(4) . . . . ?
C16 C13 C14 C15 -176.9(2) . . . . ?
C13 C14 C15 C10 -0.4(4) . . . . ?
C11 C10 C15 C14 -1.4(4) . . . . ?
C9 C10 C15 C14 179.6(2) . . . . ?
C17 O4 C16 O3 -1.6(4) . . . . ?
C17 O4 C16 C13 178.1(2) . . . . ?
C12 C13 C16 O3 -11.2(4) . . . . ?
C14 C13 C16 O3 166.9(3) . . . . ?
C12 C13 C16 O4 169.1(2) . . . . ?
C14 C13 C16 O4 -12.7(4) . . . . ?
C16 O4 C17 C21 78.6(3) . . . . ?
C16 O4 C17 C18 -163.0(2) . . . . ?
O4 C17 C18 C19 -179.1(2) . . . . ?
C21 C17 C18 C19 -59.8(3) . . . . ?
O5 N1 C19 C22 50.3(3) . . . . ?
C20 N1 C19 C22 -153.3(3) . . . . ?
O5 N1 C19 C18 169.0(3) . . . . ?
C20 N1 C19 C18 -34.5(4) . . . . ?
O5 N1 C19 C23 -68.8(3) . . . . ?
C20 N1 C19 C23 87.7(3) . . . . ?
C17 C18 C19 N1 44.3(3) . . . . ?
C17 C18 C19 C22 162.4(3) . . . . ?
C17 C18 C19 C23 -76.9(3) . . . . ?
O5 N1 C20 C25 -48.8(4) . . . . ?
C19 N1 C20 C25 154.4(3) . . . . ?
O5 N1 C20 C21 -167.1(3) . . . . ?
C19 N1 C20 C21 36.1(4) . . . . ?
O5 N1 C20 C24 70.6(3) . . . . ?
C19 N1 C20 C24 -86.2(3) . . . . ?
O4 C17 C21 C20 178.0(2) . . . . ?
C18 C17 C21 C20 61.5(3) . . . . ?
N1 C20 C21 C17 -47.4(3) . . . . ?
C25 C20 C21 C17 -165.1(3) . . . . ?
C24 C20 C21 C17 73.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.082
