# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_p

_audit_creation_method           SHELXL-97
_chemical_name_systematic        zs-spiro
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H25 N O5 S'
_chemical_formula_weight         427.50

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           monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   11.074(3)
_cell_length_b                   12.584(3)
_cell_length_c                   15.635(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.076(4)
_cell_angle_gamma                90.00
_cell_volume                     2157.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9641
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            10431
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_sigmaI/netI    0.1075
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3793
_reflns_number_gt                1536
_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)+(0.0660P)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         3793
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1692
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1679
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_restrained_S_all      0.924
_refine_ls_shift/su_max          0.003
_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 0.98863(11) 0.91327(10) 0.24559(7) 0.0770(4) Uani 1 1 d . . .
O1 O 0.8976(3) 0.9553(3) 0.18122(17) 0.1056(11) Uani 1 1 d . . .
O2 O 1.0903(3) 0.8581(2) 0.22000(17) 0.0927(10) Uani 1 1 d . . .
O3 O 1.1926(2) 0.9268(2) 0.39984(15) 0.0669(8) Uani 1 1 d . . .
O4 O 1.2361(3) 0.7720(3) 0.50211(18) 0.0935(10) Uani 1 1 d . . .
O5 O 1.4378(3) 0.7894(3) 0.5171(2) 0.1043(12) Uani 1 1 d . . .
N1 N 1.0398(3) 1.0111(2) 0.30747(19) 0.0637(9) Uani 1 1 d . . .
C1 C 0.7281(6) 0.6264(4) 0.4699(3) 0.140(2) Uani 1 1 d . . .
H1A H 0.6749 0.6683 0.4998 0.210 Uiso 1 1 calc R . .
H1B H 0.7870 0.5910 0.5111 0.210 Uiso 1 1 calc R . .
H1C H 0.6810 0.5745 0.4346 0.210 Uiso 1 1 calc R . .
C2 C 0.7932(6) 0.6979(5) 0.4133(3) 0.0902(15) Uani 1 1 d . . .
C3 C 0.7338(4) 0.7784(4) 0.3671(3) 0.0856(14) Uani 1 1 d . . .
H3 H 0.6517 0.7898 0.3704 0.103 Uiso 1 1 calc R . .
C4 C 0.7927(4) 0.8433(4) 0.3154(3) 0.0778(13) Uani 1 1 d . . .
H4 H 0.7501 0.8977 0.2841 0.093 Uiso 1 1 calc R . .
C5 C 0.9138(4) 0.8283(4) 0.3098(2) 0.0674(11) Uani 1 1 d . . .
C6 C 0.9756(4) 0.7460(4) 0.3559(3) 0.0829(14) Uani 1 1 d . . .
H6 H 1.0578 0.7343 0.3528 0.099 Uiso 1 1 calc R . .
C7 C 0.9131(6) 0.6812(4) 0.4067(3) 0.0954(16) Uani 1 1 d . . .
H7 H 0.9541 0.6252 0.4369 0.114 Uiso 1 1 calc R . .
C8 C 0.9546(4) 1.0805(3) 0.3451(3) 0.0840(13) Uani 1 1 d . . .
H8A H 0.9189 1.1325 0.3033 0.101 Uiso 1 1 calc R . .
H8B H 0.8897 1.0393 0.3648 0.101 Uiso 1 1 calc R . .
C9 C 1.0295(5) 1.1322(5) 0.4178(4) 0.133(2) Uani 1 1 d . . .
H9A H 1.0125 1.2079 0.4169 0.160 Uiso 1 1 calc R . .
H9B H 1.0102 1.1034 0.4718 0.160 Uiso 1 1 calc R . .
C10 C 1.1539(5) 1.1150(4) 0.4115(3) 0.0987(16) Uani 1 1 d . . .
H10A H 1.1981 1.0989 0.4681 0.118 Uiso 1 1 calc R . .
H10B H 1.1891 1.1785 0.3899 0.118 Uiso 1 1 calc R . .
C11 C 1.1646(4) 1.0227(3) 0.3505(2) 0.0626(11) Uani 1 1 d . . .
C12 C 1.2541(3) 1.0407(3) 0.2889(2) 0.0695(12) Uani 1 1 d . . .
H12A H 1.2328 1.1052 0.2564 0.083 Uiso 1 1 calc R . .
H12B H 1.2497 0.9820 0.2483 0.083 Uiso 1 1 calc R . .
C13 C 1.3828(4) 1.0499(3) 0.3354(3) 0.0691(12) Uani 1 1 d . . .
H13 H 1.3897 1.1170 0.3675 0.083 Uiso 1 1 calc R . .
C14 C 1.4043(4) 0.9613(4) 0.3985(2) 0.0714(12) Uani 1 1 d . . .
H14 H 1.4840 0.9427 0.4200 0.086 Uiso 1 1 calc R . .
C15 C 1.3138(4) 0.9082(3) 0.4247(2) 0.0631(11) Uani 1 1 d . . .
C16 C 1.3373(5) 0.8174(4) 0.4861(3) 0.0761(13) Uani 1 1 d . . .
C17 C 1.2494(5) 0.6837(4) 0.5614(3) 0.1231(19) Uani 1 1 d . . .
H17A H 1.1804 0.6372 0.5489 0.185 Uiso 1 1 calc R . .
H17B H 1.2538 0.7097 0.6195 0.185 Uiso 1 1 calc R . .
H17C H 1.3227 0.6455 0.5552 0.185 Uiso 1 1 calc R . .
C18 C 1.4734(4) 1.0517(4) 0.2719(3) 0.0701(12) Uani 1 1 d . . .
C19 C 1.5402(5) 1.1406(4) 0.2622(3) 0.0994(16) Uani 1 1 d . . .
H19 H 1.5320 1.1993 0.2971 0.119 Uiso 1 1 calc R . .
C20 C 1.6204(5) 1.1456(6) 0.2016(5) 0.124(2) Uani 1 1 d . . .
H20 H 1.6666 1.2065 0.1966 0.149 Uiso 1 1 calc R . .
C21 C 1.6305(6) 1.0609(7) 0.1498(4) 0.124(2) Uani 1 1 d . . .
H21 H 1.6826 1.0641 0.1082 0.149 Uiso 1 1 calc R . .
C22 C 1.5654(5) 0.9718(6) 0.1582(4) 0.1110(18) Uani 1 1 d . . .
H22 H 1.5736 0.9136 0.1228 0.133 Uiso 1 1 calc R . .
C23 C 1.4865(4) 0.9667(4) 0.2191(3) 0.0876(14) Uani 1 1 d . . .
H23 H 1.4419 0.9050 0.2244 0.105 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 O1 1.422(3) . ?
S1 O2 1.427(3) . ?
S1 N1 1.619(3) . ?
S1 C5 1.752(4) . ?
O3 C15 1.364(4) . ?
O3 C11 1.442(4) . ?
O4 C16 1.313(5) . ?
O4 C17 1.440(5) . ?
O5 C16 1.203(5) . ?
N1 C11 1.457(4) . ?
N1 C8 1.468(5) . ?
C1 C2 1.514(6) . ?
C2 C3 1.359(6) . ?
C2 C7 1.363(6) . ?
C3 C4 1.376(6) . ?
C4 C5 1.369(5) . ?
C5 C6 1.386(5) . ?
C6 C7 1.389(6) . ?
C8 C9 1.462(6) . ?
C9 C10 1.412(6) . ?
C10 C11 1.518(5) . ?
C11 C12 1.492(5) . ?
C12 C13 1.511(5) . ?
C13 C14 1.486(5) . ?
C13 C18 1.506(5) . ?
C14 C15 1.316(5) . ?
C15 C16 1.492(6) . ?
C18 C19 1.361(6) . ?
C18 C23 1.372(6) . ?
C19 C20 1.389(7) . ?
C20 C21 1.353(7) . ?
C21 C22 1.349(7) . ?
C22 C23 1.382(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
O1 S1 O2 119.40(19) . . ?
O1 S1 N1 107.11(19) . . ?
O2 S1 N1 108.27(18) . . ?
O1 S1 C5 106.7(2) . . ?
O2 S1 C5 108.6(2) . . ?
N1 S1 C5 106.04(17) . . ?
C15 O3 C11 115.1(3) . . ?
C16 O4 C17 116.5(4) . . ?
C11 N1 C8 112.1(3) . . ?
C11 N1 S1 125.6(3) . . ?
C8 N1 S1 120.1(3) . . ?
C3 C2 C7 118.6(5) . . ?
C3 C2 C1 121.3(6) . . ?
C7 C2 C1 120.1(6) . . ?
C2 C3 C4 121.4(5) . . ?
C5 C4 C3 120.3(5) . . ?
C4 C5 C6 119.1(4) . . ?
C4 C5 S1 119.9(4) . . ?
C6 C5 S1 121.0(4) . . ?
C5 C6 C7 119.2(5) . . ?
C2 C7 C6 121.4(5) . . ?
C9 C8 N1 104.5(4) . . ?
C10 C9 C8 109.3(4) . . ?
C9 C10 C11 108.9(4) . . ?
O3 C11 N1 106.4(3) . . ?
O3 C11 C12 111.1(3) . . ?
N1 C11 C12 112.9(3) . . ?
O3 C11 C10 109.5(3) . . ?
N1 C11 C10 102.4(3) . . ?
C12 C11 C10 114.0(4) . . ?
C11 C12 C13 111.6(3) . . ?
C14 C13 C18 112.9(4) . . ?
C14 C13 C12 108.2(3) . . ?
C18 C13 C12 110.8(3) . . ?
C15 C14 C13 122.0(4) . . ?
C14 C15 O3 125.9(4) . . ?
C14 C15 C16 121.2(4) . . ?
O3 C15 C16 113.0(4) . . ?
O5 C16 O4 124.2(5) . . ?
O5 C16 C15 123.5(5) . . ?
O4 C16 C15 112.3(4) . . ?
C19 C18 C23 118.0(4) . . ?
C19 C18 C13 120.5(5) . . ?
C23 C18 C13 121.4(4) . . ?
C18 C19 C20 121.6(6) . . ?
C21 C20 C19 119.1(6) . . ?
C22 C21 C20 120.5(6) . . ?
C21 C22 C23 120.3(6) . . ?
C18 C23 C22 120.6(5) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 1013252'
