# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Liu, Quanzhong'
_publ_contact_author_email       quanzhongliu@sohu.com

_publ_section_title              
;
Diastereoslective and Enantioselective Capture of Chiral
Zinc Enolate Using Nitroolefins: A Rapid Acess to Chiral
g-Nitro Carbonyl Compounds
;
_publ_contact_author_address     
;
School of Chemistry and Chemical Engineering
China West Normal University No 1 Shida Road
Nanchong 637002
Peoples' Republic of China
;
_publ_contact_author_fax         ?
_publ_contact_author_phone       ?

_publ_contact_letter             
;
Dec.29, 2010
Please consider this CIF submission for publication in
J. Org. Chem., All authors have seen
and approved of this submission.

The CIF has passed the Chester CHECKCIF routines and gives a
satisfactory PRINTCIF file.

Cheng-Yan Ni
;
_publ_requested_category         CO
_publ_requested_coeditor_name    ?
loop_
_publ_author_name
'Quanzhong Liu'
'Cheng-Yan Ni'
'Sha-Sha Kan'
'Tai-Ran Kang'

# Attachment '4d.cif'

data_4d
_database_code_depnum_ccdc_archive 'CCDC 806147'

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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H24 Br N O3'
_chemical_formula_sum            'C25 H24 Br N O3'
_chemical_formula_weight         466.36

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 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'R 3'
_symmetry_space_group_name_Hall  'R 3'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   20.3125(12)
_cell_length_b                   20.3125(12)
_cell_length_c                   15.9673(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     5705.4(6)
_cell_formula_units_Z            9
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    5458
_cell_measurement_theta_min      3.7368
_cell_measurement_theta_max      69.7417

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2160
_exptl_absorpt_coefficient_mu    2.390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5152
_exptl_absorpt_correction_T_max  0.6465
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Gemini S Ultra, Oxford Diffraction'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15602
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.74
_diffrn_reflns_theta_max         69.82
_reflns_number_total             4702
_reflns_number_gt                3179
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0505P)^2^+13.8477P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00110(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4702
_refine_ls_number_parameters     261
_refine_ls_number_restraints     89
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0842
_refine_ls_wR_factor_ref         0.1980
_refine_ls_wR_factor_gt          0.1875
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.151
_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
Br1 Br 0.49740(11) 1.07223(9) 0.41764(10) 0.2130(9) Uani 1 1 d . . .
C4 C 0.3457(4) 0.9035(4) 0.2092(4) 0.0947(17) Uani 1 1 d . . .
O3 O 0.2421(3) 0.6878(3) 0.2138(4) 0.1329(19) Uani 1 1 d . . .
C11 C 0.2338(4) 0.7427(4) 0.3387(6) 0.107(2) Uani 1 1 d . . .
C7 C 0.2912(4) 0.8464(4) 0.1467(5) 0.0985(18) Uani 1 1 d . . .
H7 H 0.2764 0.8742 0.1081 0.118 Uiso 1 1 calc R . .
C10 C 0.2337(4) 0.7381(4) 0.2490(6) 0.110(2) Uani 1 1 d . . .
C9 C 0.2187(4) 0.7901(4) 0.1957(5) 0.1064(19) Uani 1 1 d U . .
H9 H 0.2053 0.8199 0.2331 0.128 Uiso 1 1 calc R . .
C5 C 0.3380(5) 0.9630(4) 0.2322(5) 0.117(2) Uani 1 1 d . . .
H5 H 0.3021 0.9709 0.2048 0.140 Uiso 1 1 calc R . .
C8 C 0.3246(4) 0.8087(4) 0.0947(5) 0.115(2) Uani 1 1 d U . .
H8B H 0.3481 0.7881 0.1311 0.138 Uiso 1 1 calc R . .
H8A H 0.2845 0.7670 0.0635 0.138 Uiso 1 1 calc R . .
C3 C 0.3997(4) 0.8953(4) 0.2495(5) 0.108(2) Uani 1 1 d . . .
H3 H 0.4057 0.8543 0.2348 0.129 Uiso 1 1 calc R . .
C16 C 0.2363(4) 0.6855(5) 0.3865(8) 0.132(3) Uani 1 1 d . . .
H16 H 0.2377 0.6459 0.3590 0.159 Uiso 1 1 calc R . .
C2 C 0.4466(5) 0.9438(5) 0.3113(6) 0.130(3) Uani 1 1 d . . .
H2 H 0.4842 0.9373 0.3367 0.156 Uiso 1 1 calc R . .
C18 C 0.1342(4) 0.7941(5) 0.0753(5) 0.153(3) Uani 1 1 d GU . .
C19 C 0.1172(5) 0.8460(5) 0.1118(5) 0.180(4) Uani 1 1 d GU . .
H19 H 0.1155 0.8491 0.1698 0.216 Uiso 1 1 calc R . .
C20 C 0.1026(5) 0.8932(5) 0.0616(7) 0.234(5) Uani 1 1 d GU . .
H20 H 0.0913 0.9279 0.0860 0.281 Uiso 1 1 calc R . .
C21 C 0.1051(5) 0.8885(6) -0.0251(7) 0.231(5) Uani 1 1 d GU . .
H21 H 0.0954 0.9201 -0.0587 0.277 Uiso 1 1 calc R . .
C22 C 0.1221(5) 0.8367(7) -0.0616(4) 0.217(5) Uani 1 1 d GU . .
H22 H 0.1238 0.8336 -0.1195 0.260 Uiso 1 1 calc R . .
C23 C 0.1367(5) 0.7895(6) -0.0113(6) 0.203(4) Uani 1 1 d GU . .
H23 H 0.1480 0.7548 -0.0358 0.244 Uiso 1 1 calc R . .
C6 C 0.3807(6) 1.0122(5) 0.2939(7) 0.136(3) Uani 1 1 d . . .
H6 H 0.3735 1.0522 0.3095 0.163 Uiso 1 1 calc R . .
C15 C 0.2366(6) 0.6867(8) 0.4757(8) 0.157(4) Uani 1 1 d . . .
H15 H 0.2353 0.6469 0.5060 0.188 Uiso 1 1 calc R . .
C13 C 0.2363(6) 0.8017(7) 0.4684(9) 0.167(4) Uani 1 1 d . . .
H13 H 0.2363 0.8420 0.4960 0.200 Uiso 1 1 calc R . .
N1 N 0.3812(5) 0.8628(6) 0.0365(5) 0.137(3) Uani 1 1 d U . .
C14 C 0.2389(6) 0.7471(7) 0.5161(7) 0.144(3) Uani 1 1 d . . .
H14 H 0.2420 0.7510 0.5742 0.173 Uiso 1 1 calc R . .
C1 C 0.4346(5) 1.0009(5) 0.3323(5) 0.127(3) Uani 1 1 d . . .
C12 C 0.2338(5) 0.8010(5) 0.3810(6) 0.135(3) Uani 1 1 d . . .
H12 H 0.2321 0.8399 0.3520 0.162 Uiso 1 1 calc R . .
O1 O 0.3781(6) 0.9068(6) 0.0038(7) 0.220(4) Uani 1 1 d U . .
O2 O 0.4364(6) 0.8607(7) 0.0257(6) 0.221(4) Uani 1 1 d U . .
C24 C 0.0759(5) 0.6903(6) 0.1908(8) 0.162(4) Uani 1 1 d U . .
H24B H 0.0650 0.7224 0.2263 0.195 Uiso 1 1 calc R . .
H24A H 0.0876 0.6589 0.2267 0.195 Uiso 1 1 calc R . .
C25 C 0.0021(7) 0.6364(7) 0.1338(8) 0.200(5) Uani 1 1 d U . .
H25A H 0.0108 0.6006 0.1037 0.299 Uiso 1 1 calc R . .
H25C H -0.0066 0.6672 0.0948 0.299 Uiso 1 1 calc R . .
H25B H -0.0417 0.6095 0.1692 0.299 Uiso 1 1 calc R . .
C17 C 0.1471(5) 0.7419(5) 0.1329(6) 0.132(2) Uani 1 1 d U . .
H17 H 0.1581 0.7086 0.0983 0.158 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.2547(18) 0.1783(12) 0.1700(11) -0.0647(10) -0.0470(11) 0.0811(12)
C4 0.088(4) 0.083(4) 0.117(5) 0.007(3) 0.009(3) 0.046(3)
O3 0.144(4) 0.102(3) 0.166(5) 0.008(3) 0.038(4) 0.071(3)
C11 0.092(4) 0.084(4) 0.142(6) 0.006(4) 0.020(4) 0.041(3)
C7 0.093(4) 0.089(4) 0.115(5) 0.001(3) 0.003(4) 0.046(4)
C10 0.099(5) 0.085(4) 0.136(6) 0.001(4) 0.025(4) 0.039(4)
C9 0.103(4) 0.093(4) 0.124(5) -0.001(4) 0.011(4) 0.049(4)
C5 0.117(6) 0.093(5) 0.138(6) -0.001(5) -0.005(5) 0.050(4)
C8 0.109(5) 0.103(5) 0.118(5) -0.012(4) 0.014(4) 0.042(4)
C3 0.120(5) 0.088(4) 0.116(5) -0.004(4) 0.010(4) 0.053(4)
C16 0.104(5) 0.104(5) 0.197(10) 0.000(6) 0.004(6) 0.057(4)
C2 0.133(6) 0.113(6) 0.146(7) -0.007(5) 0.004(5) 0.064(5)
C18 0.103(5) 0.171(7) 0.148(6) -0.006(5) -0.016(5) 0.041(5)
C19 0.171(8) 0.171(7) 0.209(7) 0.024(6) -0.016(6) 0.094(6)
C20 0.235(10) 0.234(9) 0.240(8) 0.028(7) -0.035(8) 0.122(8)
C21 0.203(9) 0.246(9) 0.222(8) 0.025(7) -0.045(8) 0.096(7)
C22 0.165(8) 0.245(10) 0.210(8) 0.035(6) -0.023(7) 0.081(7)
C23 0.160(8) 0.225(9) 0.187(6) 0.014(6) -0.003(7) 0.068(6)
C6 0.149(7) 0.093(5) 0.173(8) -0.006(5) 0.009(7) 0.066(5)
C15 0.136(7) 0.176(10) 0.146(9) 0.045(8) 0.016(7) 0.070(7)
C13 0.183(10) 0.139(9) 0.181(11) -0.031(8) 0.025(9) 0.081(8)
N1 0.137(6) 0.178(7) 0.122(5) 0.030(5) 0.028(4) 0.098(6)
C14 0.145(8) 0.148(9) 0.148(8) -0.002(7) 0.011(6) 0.080(7)
C1 0.131(6) 0.111(6) 0.116(6) -0.011(5) -0.016(5) 0.042(5)
C12 0.153(8) 0.115(6) 0.138(8) -0.006(5) 0.023(6) 0.067(5)
O1 0.226(7) 0.222(7) 0.234(8) 0.087(6) 0.078(6) 0.128(6)
O2 0.173(6) 0.283(8) 0.217(7) 0.070(6) 0.048(5) 0.121(6)
C24 0.108(5) 0.126(7) 0.228(11) 0.007(6) 0.019(6) 0.039(5)
C25 0.148(6) 0.182(8) 0.230(9) -0.025(7) 0.007(6) 0.053(5)
C17 0.107(4) 0.120(5) 0.159(6) -0.025(4) 0.007(4) 0.049(4)

_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
Br1 C1 1.933(8) . ?
C4 C5 1.345(10) . ?
C4 C3 1.351(10) . ?
C4 C7 1.512(9) . ?
O3 C10 1.251(8) . ?
C11 C12 1.366(11) . ?
C11 C16 1.411(12) . ?
C11 C10 1.435(11) . ?
C7 C8 1.502(9) . ?
C7 C9 1.551(9) . ?
C7 H7 0.9800 . ?
C10 C9 1.500(10) . ?
C9 C17 1.630(11) . ?
C9 H9 0.9800 . ?
C5 C6 1.362(12) . ?
C5 H5 0.9300 . ?
C8 N1 1.458(10) . ?
C8 H8B 0.9700 . ?
C8 H8A 0.9700 . ?
C3 C2 1.383(11) . ?
C3 H3 0.9300 . ?
C16 C15 1.425(14) . ?
C16 H16 0.9300 . ?
C2 C1 1.341(12) . ?
C2 H2 0.9300 . ?
C18 C19 1.3900 . ?
C18 C23 1.3900 . ?
C18 C17 1.523(11) . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 C21 1.3900 . ?
C20 H20 0.9300 . ?
C21 C22 1.3900 . ?
C21 H21 0.9300 . ?
C22 C23 1.3900 . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C6 C1 1.371(12) . ?
C6 H6 0.9300 . ?
C15 C14 1.367(15) . ?
C15 H15 0.9300 . ?
C13 C14 1.367(15) . ?
C13 C12 1.396(15) . ?
C13 H13 0.9300 . ?
N1 O1 1.064(10) . ?
N1 O2 1.156(10) . ?
C14 H14 0.9300 . ?
C12 H12 0.9300 . ?
C24 C17 1.591(13) . ?
C24 C25 1.624(15) . ?
C24 H24B 0.9700 . ?
C24 H24A 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25C 0.9600 . ?
C25 H25B 0.9600 . ?
C17 H17 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
C5 C4 C3 116.6(7) . . ?
C5 C4 C7 120.0(7) . . ?
C3 C4 C7 123.3(6) . . ?
C12 C11 C16 117.5(9) . . ?
C12 C11 C10 123.3(8) . . ?
C16 C11 C10 119.2(8) . . ?
C8 C7 C4 114.3(6) . . ?
C8 C7 C9 114.1(6) . . ?
C4 C7 C9 107.1(6) . . ?
C8 C7 H7 107.0 . . ?
C4 C7 H7 107.0 . . ?
C9 C7 H7 107.0 . . ?
O3 C10 C11 120.3(7) . . ?
O3 C10 C9 118.6(8) . . ?
C11 C10 C9 121.0(7) . . ?
C10 C9 C7 110.7(6) . . ?
C10 C9 C17 111.1(6) . . ?
C7 C9 C17 111.4(6) . . ?
C10 C9 H9 107.8 . . ?
C7 C9 H9 107.8 . . ?
C17 C9 H9 107.8 . . ?
C4 C5 C6 122.6(8) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
N1 C8 C7 110.9(7) . . ?
N1 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
N1 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
H8B C8 H8A 108.1 . . ?
C4 C3 C2 124.4(7) . . ?
C4 C3 H3 117.8 . . ?
C2 C3 H3 117.8 . . ?
C11 C16 C15 122.0(9) . . ?
C11 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C1 C2 C3 115.8(9) . . ?
C1 C2 H2 122.1 . . ?
C3 C2 H2 122.1 . . ?
C19 C18 C23 120.0 . . ?
C19 C18 C17 118.1(7) . . ?
C23 C18 C17 121.9(7) . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 120.0 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 120.0 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C18 120.0 . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
C5 C6 C1 118.0(8) . . ?
C5 C6 H6 121.0 . . ?
C1 C6 H6 121.0 . . ?
C14 C15 C16 118.9(11) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C14 C13 C12 124.5(10) . . ?
C14 C13 H13 117.8 . . ?
C12 C13 H13 117.8 . . ?
O1 N1 O2 115.0(11) . . ?
O1 N1 C8 126.1(10) . . ?
O2 N1 C8 118.8(10) . . ?
C13 C14 C15 117.8(11) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
C2 C1 C6 122.6(8) . . ?
C2 C1 Br1 119.1(8) . . ?
C6 C1 Br1 118.2(8) . . ?
C11 C12 C13 119.1(10) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C17 C24 C25 110.3(9) . . ?
C17 C24 H24B 109.6 . . ?
C25 C24 H24B 109.6 . . ?
C17 C24 H24A 109.6 . . ?
C25 C24 H24A 109.6 . . ?
H24B C24 H24A 108.1 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25C C25 H25B 109.5 . . ?
C18 C17 C24 113.1(8) . . ?
C18 C17 C9 111.5(7) . . ?
C24 C17 C9 106.3(8) . . ?
C18 C17 H17 108.6 . . ?
C24 C17 H17 108.6 . . ?
C9 C17 H17 108.6 . . ?

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
C5 C4 C7 C8 150.6(7) . . . . ?
C3 C4 C7 C8 -34.7(10) . . . . ?
C5 C4 C7 C9 -82.0(8) . . . . ?
C3 C4 C7 C9 92.6(8) . . . . ?
C12 C11 C10 O3 172.2(8) . . . . ?
C16 C11 C10 O3 -6.0(10) . . . . ?
C12 C11 C10 C9 -11.6(11) . . . . ?
C16 C11 C10 C9 170.2(7) . . . . ?
O3 C10 C9 C7 -71.5(8) . . . . ?
C11 C10 C9 C7 112.2(7) . . . . ?
O3 C10 C9 C17 52.8(8) . . . . ?
C11 C10 C9 C17 -123.4(7) . . . . ?
C8 C7 C9 C10 54.9(8) . . . . ?
C4 C7 C9 C10 -72.6(7) . . . . ?
C8 C7 C9 C17 -69.3(8) . . . . ?
C4 C7 C9 C17 163.2(6) . . . . ?
C3 C4 C5 C6 -1.4(12) . . . . ?
C7 C4 C5 C6 173.6(8) . . . . ?
C4 C7 C8 N1 -69.1(8) . . . . ?
C9 C7 C8 N1 167.1(7) . . . . ?
C5 C4 C3 C2 -0.4(11) . . . . ?
C7 C4 C3 C2 -175.2(7) . . . . ?
C12 C11 C16 C15 1.7(12) . . . . ?
C10 C11 C16 C15 180.0(8) . . . . ?
C4 C3 C2 C1 1.8(12) . . . . ?
C23 C18 C19 C20 0.0 . . . . ?
C17 C18 C19 C20 -178.0(7) . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C21 C22 C23 C18 0.0 . . . . ?
C19 C18 C23 C22 0.0 . . . . ?
C17 C18 C23 C22 178.0(7) . . . . ?
C4 C5 C6 C1 1.5(14) . . . . ?
C11 C16 C15 C14 -3.7(14) . . . . ?
C7 C8 N1 O1 -37.6(15) . . . . ?
C7 C8 N1 O2 139.6(11) . . . . ?
C12 C13 C14 C15 -1.9(17) . . . . ?
C16 C15 C14 C13 3.7(15) . . . . ?
C3 C2 C1 C6 -1.7(14) . . . . ?
C3 C2 C1 Br1 -179.7(6) . . . . ?
C5 C6 C1 C2 0.1(15) . . . . ?
C5 C6 C1 Br1 178.2(7) . . . . ?
C16 C11 C12 C13 0.2(13) . . . . ?
C10 C11 C12 C13 -178.0(8) . . . . ?
C14 C13 C12 C11 -0.1(17) . . . . ?
C19 C18 C17 C24 59.0(9) . . . . ?
C23 C18 C17 C24 -119.0(8) . . . . ?
C19 C18 C17 C9 -60.8(8) . . . . ?
C23 C18 C17 C9 121.2(6) . . . . ?
C25 C24 C17 C18 60.2(11) . . . . ?
C25 C24 C17 C9 -177.1(8) . . . . ?
C10 C9 C17 C18 -177.0(7) . . . . ?
C7 C9 C17 C18 -53.0(8) . . . . ?
C10 C9 C17 C24 59.3(8) . . . . ?
C7 C9 C17 C24 -176.8(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        69.82
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.066

# Attachment '5a.cif'

data_5a
_database_code_depnum_ccdc_archive 'CCDC 816318'

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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H33 N O2 S'
_chemical_formula_weight         495.65
_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'
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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   7.4163(3)
_cell_length_b                   14.0432(6)
_cell_length_c                   25.9274(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2700.30(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    4396
_cell_measurement_theta_min      2.8951
_cell_measurement_theta_max      29.1551

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9428
_exptl_absorpt_correction_T_max  0.9651
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Gemini S Ultra, Oxford Diffraction'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14601
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         26.37
_reflns_number_total             5528
_reflns_number_gt                3728
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0365P)^2^+0.1073P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   -0.08(8)
_refine_ls_number_reflns         5528
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
S1 S 0.50859(10) 0.38907(5) 0.18488(2) 0.05191(19) Uani 1 1 d . . .
O1 O 0.4209(3) 0.29806(12) 0.18479(7) 0.0641(5) Uani 1 1 d . . .
N1 N 0.5269(3) 0.42071(13) 0.12511(7) 0.0447(5) Uani 1 1 d . . .
O2 O 0.6841(3) 0.40012(14) 0.20745(7) 0.0659(5) Uani 1 1 d . . .
C11 C 0.4528(3) 0.44264(18) 0.03627(9) 0.0449(6) Uani 1 1 d . . .
H11 H 0.3813 0.5005 0.0310 0.054 Uiso 1 1 calc R . .
C12 C 0.4241(3) 0.37741(18) -0.00971(9) 0.0440(6) Uani 1 1 d . . .
C29 C 0.1316(4) 0.6132(2) 0.24946(10) 0.0601(8) Uani 1 1 d . . .
C10 C 0.6500(3) 0.47223(17) 0.04764(9) 0.0438(6) Uani 1 1 d . . .
H10 H 0.7256 0.4156 0.0430 0.053 Uiso 1 1 calc R . .
C26 C 0.3620(4) 0.47127(18) 0.21469(10) 0.0468(7) Uani 1 1 d . . .
C7 C 0.7294(4) 0.55195(18) 0.01359(10) 0.0488(7) Uani 1 1 d . . .
H7 H 0.6619 0.6104 0.0208 0.059 Uiso 1 1 calc R . .
C18 C 0.3894(4) 0.3949(2) 0.08681(9) 0.0545(7) Uani 1 1 d . . .
H18B H 0.2718 0.4186 0.0970 0.065 Uiso 1 1 calc R . .
H18A H 0.3825 0.3263 0.0828 0.065 Uiso 1 1 calc R . .
C20 C 0.5886(4) 0.59644(19) 0.12072(9) 0.0497(7) Uani 1 1 d . . .
C17 C 0.3146(4) 0.4043(2) -0.05038(10) 0.0533(7) Uani 1 1 d . . .
H17 H 0.2573 0.4631 -0.0494 0.064 Uiso 1 1 calc R . .
C13 C 0.5056(4) 0.28836(17) -0.01204(10) 0.0526(7) Uani 1 1 d . . .
H13 H 0.5792 0.2683 0.0149 0.063 Uiso 1 1 calc R . .
C27 C 0.1777(4) 0.46112(19) 0.20875(10) 0.0533(7) Uani 1 1 d . . .
H27 H 0.1306 0.4068 0.1933 0.064 Uiso 1 1 calc R . .
C4 C 0.7099(4) 0.53057(18) -0.04370(10) 0.0496(7) Uani 1 1 d . . .
C19 C 0.6482(4) 0.49591(18) 0.10625(9) 0.0451(6) Uani 1 1 d . . .
H19 H 0.7690 0.4848 0.1203 0.054 Uiso 1 1 calc R . .
C8 C 0.9284(4) 0.5704(2) 0.02755(11) 0.0598(8) Uani 1 1 d . . .
H8B H 0.9372 0.5812 0.0644 0.072 Uiso 1 1 calc R . .
H8A H 0.9981 0.5138 0.0195 0.072 Uiso 1 1 calc R . .
C6 C 0.5870(5) 0.5674(3) -0.12740(14) 0.0822(11) Uani 1 1 d . . .
H6 H 0.5140 0.6055 -0.1480 0.099 Uiso 1 1 calc R . .
C31 C 0.4309(4) 0.5504(2) 0.23940(10) 0.0588(8) Uani 1 1 d . . .
H31 H 0.5546 0.5561 0.2445 0.071 Uiso 1 1 calc R . .
C28 C 0.0636(4) 0.5324(2) 0.22601(11) 0.0604(8) Uani 1 1 d . . .
H28 H -0.0603 0.5258 0.2218 0.072 Uiso 1 1 calc R . .
C15 C 0.3713(4) 0.2584(2) -0.09418(12) 0.0694(10) Uani 1 1 d . . .
H15 H 0.3549 0.2187 -0.1225 0.083 Uiso 1 1 calc R . .
C14 C 0.4787(4) 0.2297(2) -0.05371(12) 0.0632(8) Uani 1 1 d . . .
H14 H 0.5335 0.1702 -0.0546 0.076 Uiso 1 1 calc R . .
C21 C 0.4113(4) 0.6265(2) 0.11576(11) 0.0610(8) Uani 1 1 d . . .
H21 H 0.3258 0.5851 0.1022 0.073 Uiso 1 1 calc R . .
C16 C 0.2888(4) 0.3452(2) -0.09251(11) 0.0660(9) Uani 1 1 d . . .
H16 H 0.2155 0.3647 -0.1196 0.079 Uiso 1 1 calc R . .
C3 C 0.8002(4) 0.4552(2) -0.06620(11) 0.0597(8) Uani 1 1 d . . .
H3 H 0.8737 0.4169 -0.0459 0.072 Uiso 1 1 calc R . .
C25 C 0.7100(5) 0.6588(2) 0.14182(11) 0.0703(9) Uani 1 1 d . . .
H25 H 0.8293 0.6400 0.1463 0.084 Uiso 1 1 calc R . .
C30 C 0.3164(5) 0.6209(2) 0.25662(10) 0.0634(8) Uani 1 1 d . . .
H30 H 0.3635 0.6741 0.2732 0.076 Uiso 1 1 calc R . .
C5 C 0.6031(4) 0.5865(2) -0.07484(12) 0.0652(9) Uani 1 1 d . . .
H5 H 0.5409 0.6376 -0.0606 0.078 Uiso 1 1 calc R . .
C9 C 1.0103(5) 0.6543(2) -0.00028(13) 0.0862(11) Uani 1 1 d . . .
H9A H 1.0106 0.6421 -0.0367 0.129 Uiso 1 1 calc R . .
H9C H 1.1318 0.6636 0.0114 0.129 Uiso 1 1 calc R . .
H9B H 0.9406 0.7104 0.0067 0.129 Uiso 1 1 calc R . .
C32 C 0.0079(6) 0.6938(2) 0.26597(12) 0.0867(10) Uani 1 1 d . . .
H32A H -0.1113 0.6824 0.2529 0.130 Uiso 1 1 calc R . .
H32C H 0.0526 0.7529 0.2525 0.130 Uiso 1 1 calc R . .
H32B H 0.0042 0.6969 0.3029 0.130 Uiso 1 1 calc R . .
C2 C 0.7837(5) 0.4356(2) -0.11813(14) 0.0782(10) Uani 1 1 d . . .
H2 H 0.8438 0.3837 -0.1324 0.094 Uiso 1 1 calc R . .
C1 C 0.6788(6) 0.4925(3) -0.14863(13) 0.0858(12) Uani 1 1 d . . .
H1 H 0.6699 0.4804 -0.1838 0.103 Uiso 1 1 calc R . .
C23 C 0.4815(7) 0.7784(2) 0.15097(14) 0.0929(12) Uani 1 1 d . . .
H23 H 0.4458 0.8392 0.1609 0.111 Uiso 1 1 calc R . .
C22 C 0.3598(5) 0.7170(2) 0.13069(12) 0.0804(10) Uani 1 1 d . . .
H22 H 0.2403 0.7358 0.1268 0.096 Uiso 1 1 calc R . .
C24 C 0.6564(6) 0.7509(3) 0.15682(14) 0.0914(12) Uani 1 1 d . . .
H24 H 0.7404 0.7929 0.1707 0.110 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0563(4) 0.0515(4) 0.0479(4) 0.0060(3) -0.0041(4) 0.0009(4)
O1 0.0796(14) 0.0436(11) 0.0690(13) 0.0112(9) 0.0019(11) -0.0043(10)
N1 0.0453(13) 0.0466(12) 0.0422(12) -0.0002(9) -0.0022(11) -0.0031(11)
O2 0.0562(12) 0.0813(14) 0.0603(12) 0.0108(11) -0.0152(10) 0.0034(11)
C11 0.0401(16) 0.0496(15) 0.0449(15) -0.0032(11) -0.0027(12) 0.0028(12)
C12 0.0384(14) 0.0504(16) 0.0431(15) -0.0040(12) 0.0015(12) -0.0045(13)
C29 0.072(2) 0.0628(19) 0.0458(17) -0.0064(15) 0.0048(15) -0.0014(18)
C10 0.0417(15) 0.0428(15) 0.0468(15) -0.0024(12) 0.0028(12) 0.0003(12)
C26 0.0517(18) 0.0488(17) 0.0399(15) 0.0010(12) 0.0006(12) -0.0069(14)
C7 0.0531(17) 0.0434(15) 0.0499(17) -0.0021(12) 0.0000(13) -0.0005(13)
C18 0.0490(18) 0.0647(18) 0.0497(17) -0.0036(14) -0.0010(13) -0.0128(16)
C20 0.0630(18) 0.0489(18) 0.0372(15) 0.0017(12) -0.0014(13) -0.0039(15)
C17 0.0479(17) 0.0627(18) 0.0493(17) -0.0006(14) -0.0051(13) 0.0008(14)
C13 0.0422(15) 0.0515(16) 0.0642(17) -0.0074(13) -0.0020(15) -0.0036(15)
C27 0.0548(18) 0.0564(17) 0.0487(16) -0.0084(13) 0.0051(14) -0.0112(15)
C4 0.0497(18) 0.0518(17) 0.0471(16) 0.0030(13) -0.0008(13) -0.0089(14)
C19 0.0433(16) 0.0469(16) 0.0449(15) 0.0006(11) -0.0065(12) -0.0025(13)
C8 0.0554(18) 0.071(2) 0.0530(17) -0.0013(14) -0.0037(14) -0.0149(16)
C6 0.092(3) 0.085(3) 0.070(2) 0.0275(19) -0.026(2) -0.017(2)
C31 0.0556(18) 0.074(2) 0.0467(17) -0.0068(14) -0.0036(14) -0.0149(17)
C28 0.0502(19) 0.070(2) 0.0604(19) -0.0104(15) 0.0077(14) -0.0078(16)
C15 0.072(2) 0.080(2) 0.056(2) -0.0245(16) 0.0192(17) -0.031(2)
C14 0.0505(19) 0.0574(17) 0.082(2) -0.0183(16) 0.0150(18) -0.0087(16)
C21 0.076(2) 0.057(2) 0.0501(18) -0.0076(14) -0.0052(16) 0.0117(17)
C16 0.064(2) 0.088(2) 0.0459(18) -0.0007(16) -0.0082(16) -0.0204(19)
C3 0.061(2) 0.0670(19) 0.0506(18) -0.0063(14) 0.0007(15) -0.0007(17)
C25 0.084(3) 0.061(2) 0.066(2) -0.0075(16) -0.0061(18) -0.0118(19)
C30 0.075(2) 0.0638(19) 0.0510(18) -0.0185(15) 0.0020(17) -0.0151(19)
C5 0.072(2) 0.0561(19) 0.067(2) 0.0119(15) -0.0110(17) -0.0044(17)
C9 0.082(3) 0.080(2) 0.097(2) 0.0104(18) -0.009(2) -0.033(2)
C32 0.102(3) 0.080(2) 0.078(2) -0.0171(17) 0.002(2) 0.015(2)
C2 0.079(3) 0.088(3) 0.067(2) -0.0161(19) 0.007(2) -0.011(2)
C1 0.108(3) 0.098(3) 0.051(2) 0.000(2) -0.006(2) -0.027(3)
C23 0.140(4) 0.048(2) 0.091(3) -0.0075(17) -0.003(3) 0.017(3)
C22 0.107(3) 0.069(2) 0.066(2) -0.0027(18) -0.005(2) 0.026(2)
C24 0.114(3) 0.058(2) 0.102(3) -0.0180(19) -0.007(3) -0.017(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 O1 1.4341(18) . ?
S1 O2 1.4355(19) . ?
S1 N1 1.618(2) . ?
S1 C26 1.764(3) . ?
N1 C18 1.469(3) . ?
N1 C19 1.471(3) . ?
C11 C12 1.518(3) . ?
C11 C18 1.545(3) . ?
C11 C10 1.549(3) . ?
C11 H11 0.9800 . ?
C12 C17 1.383(3) . ?
C12 C13 1.391(3) . ?
C29 C28 1.383(4) . ?
C29 C30 1.387(4) . ?
C29 C32 1.518(4) . ?
C10 C7 1.542(3) . ?
C10 C19 1.556(3) . ?
C10 H10 0.9800 . ?
C26 C31 1.380(3) . ?
C26 C27 1.383(4) . ?
C7 C4 1.522(3) . ?
C7 C8 1.542(4) . ?
C7 H7 0.9800 . ?
C18 H18B 0.9700 . ?
C18 H18A 0.9700 . ?
C20 C25 1.370(4) . ?
C20 C21 1.387(4) . ?
C20 C19 1.526(3) . ?
C17 C16 1.385(4) . ?
C17 H17 0.9300 . ?
C13 C14 1.373(3) . ?
C13 H13 0.9300 . ?
C27 C28 1.384(4) . ?
C27 H27 0.9300 . ?
C4 C5 1.376(4) . ?
C4 C3 1.382(3) . ?
C19 H19 0.9800 . ?
C8 C9 1.509(4) . ?
C8 H8B 0.9700 . ?
C8 H8A 0.9700 . ?
C6 C1 1.368(5) . ?
C6 C5 1.394(4) . ?
C6 H6 0.9300 . ?
C31 C30 1.379(4) . ?
C31 H31 0.9300 . ?
C28 H28 0.9300 . ?
C15 C16 1.365(4) . ?
C15 C14 1.378(4) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C21 C22 1.382(4) . ?
C21 H21 0.9300 . ?
C16 H16 0.9300 . ?
C3 C2 1.380(4) . ?
C3 H3 0.9300 . ?
C25 C24 1.408(4) . ?
C25 H25 0.9300 . ?
C30 H30 0.9300 . ?
C5 H5 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9C 0.9600 . ?
C9 H9B 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32C 0.9600 . ?
C32 H32B 0.9600 . ?
C2 C1 1.368(4) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C23 C22 1.356(5) . ?
C23 C24 1.362(5) . ?
C23 H23 0.9300 . ?
C22 H22 0.9300 . ?
C24 H24 0.9300 . ?

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 120.55(12) . . ?
O1 S1 N1 106.33(11) . . ?
O2 S1 N1 106.55(11) . . ?
O1 S1 C26 107.72(12) . . ?
O2 S1 C26 108.04(13) . . ?
N1 S1 C26 106.95(11) . . ?
C18 N1 C19 112.15(19) . . ?
C18 N1 S1 121.45(16) . . ?
C19 N1 S1 124.53(16) . . ?
C12 C11 C18 111.2(2) . . ?
C12 C11 C10 116.3(2) . . ?
C18 C11 C10 104.0(2) . . ?
C12 C11 H11 108.3 . . ?
C18 C11 H11 108.3 . . ?
C10 C11 H11 108.3 . . ?
C17 C12 C13 117.9(2) . . ?
C17 C12 C11 121.1(2) . . ?
C13 C12 C11 121.1(2) . . ?
C28 C29 C30 118.9(3) . . ?
C28 C29 C32 121.0(3) . . ?
C30 C29 C32 120.1(3) . . ?
C7 C10 C11 116.5(2) . . ?
C7 C10 C19 114.0(2) . . ?
C11 C10 C19 103.60(19) . . ?
C7 C10 H10 107.4 . . ?
C11 C10 H10 107.4 . . ?
C19 C10 H10 107.4 . . ?
C31 C26 C27 120.0(3) . . ?
C31 C26 S1 120.1(2) . . ?
C27 C26 S1 119.5(2) . . ?
C4 C7 C8 110.7(2) . . ?
C4 C7 C10 112.3(2) . . ?
C8 C7 C10 110.7(2) . . ?
C4 C7 H7 107.7 . . ?
C8 C7 H7 107.7 . . ?
C10 C7 H7 107.7 . . ?
N1 C18 C11 104.8(2) . . ?
N1 C18 H18B 110.8 . . ?
C11 C18 H18B 110.8 . . ?
N1 C18 H18A 110.8 . . ?
C11 C18 H18A 110.8 . . ?
H18B C18 H18A 108.9 . . ?
C25 C20 C21 117.8(3) . . ?
C25 C20 C19 120.0(3) . . ?
C21 C20 C19 122.2(3) . . ?
C12 C17 C16 121.3(3) . . ?
C12 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C26 C27 C28 119.6(3) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 C7 121.0(3) . . ?
C3 C4 C7 121.1(2) . . ?
N1 C19 C20 113.9(2) . . ?
N1 C19 C10 100.16(18) . . ?
C20 C19 C10 116.1(2) . . ?
N1 C19 H19 108.7 . . ?
C20 C19 H19 108.7 . . ?
C10 C19 H19 108.7 . . ?
C9 C8 C7 113.8(3) . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
H8B C8 H8A 107.7 . . ?
C1 C6 C5 119.9(3) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C30 C31 C26 120.0(3) . . ?
C30 C31 H31 120.0 . . ?
C26 C31 H31 120.0 . . ?
C29 C28 C27 120.8(3) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C22 C21 C20 121.1(3) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C20 C25 C24 120.8(4) . . ?
C20 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C31 C30 C29 120.6(3) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9C C9 H9B 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32C C32 H32B 109.5 . . ?
C1 C2 C3 119.8(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C1 C6 120.0(3) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C22 C23 C24 119.8(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C22 C21 120.6(4) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C23 C24 C25 119.9(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?

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 N1 C18 33.5(2) . . . . ?
O2 S1 N1 C18 163.27(19) . . . . ?
C26 S1 N1 C18 -81.4(2) . . . . ?
O1 S1 N1 C19 -163.32(19) . . . . ?
O2 S1 N1 C19 -33.6(2) . . . . ?
C26 S1 N1 C19 81.8(2) . . . . ?
C18 C11 C12 C17 120.0(3) . . . . ?
C10 C11 C12 C17 -121.2(3) . . . . ?
C18 C11 C12 C13 -59.3(3) . . . . ?
C10 C11 C12 C13 59.5(3) . . . . ?
C12 C11 C10 C7 78.8(3) . . . . ?
C18 C11 C10 C7 -158.6(2) . . . . ?
C12 C11 C10 C19 -155.1(2) . . . . ?
C18 C11 C10 C19 -32.5(2) . . . . ?
O1 S1 C26 C31 152.8(2) . . . . ?
O2 S1 C26 C31 21.1(2) . . . . ?
N1 S1 C26 C31 -93.2(2) . . . . ?
O1 S1 C26 C27 -33.6(2) . . . . ?
O2 S1 C26 C27 -165.3(2) . . . . ?
N1 S1 C26 C27 80.4(2) . . . . ?
C11 C10 C7 C4 -53.1(3) . . . . ?
C19 C10 C7 C4 -173.7(2) . . . . ?
C11 C10 C7 C8 -177.3(2) . . . . ?
C19 C10 C7 C8 62.0(3) . . . . ?
C19 N1 C18 C11 12.1(3) . . . . ?
S1 N1 C18 C11 177.18(16) . . . . ?
C12 C11 C18 N1 139.4(2) . . . . ?
C10 C11 C18 N1 13.5(3) . . . . ?
C13 C12 C17 C16 -1.0(4) . . . . ?
C11 C12 C17 C16 179.6(3) . . . . ?
C17 C12 C13 C14 0.5(4) . . . . ?
C11 C12 C13 C14 179.9(2) . . . . ?
C31 C26 C27 C28 2.4(4) . . . . ?
S1 C26 C27 C28 -171.2(2) . . . . ?
C8 C7 C4 C5 -120.8(3) . . . . ?
C10 C7 C4 C5 115.0(3) . . . . ?
C8 C7 C4 C3 58.4(3) . . . . ?
C10 C7 C4 C3 -65.8(3) . . . . ?
C18 N1 C19 C20 92.8(2) . . . . ?
S1 N1 C19 C20 -71.8(3) . . . . ?
C18 N1 C19 C10 -31.9(3) . . . . ?
S1 N1 C19 C10 163.54(17) . . . . ?
C25 C20 C19 N1 131.6(3) . . . . ?
C21 C20 C19 N1 -45.0(3) . . . . ?
C25 C20 C19 C10 -112.8(3) . . . . ?
C21 C20 C19 C10 70.6(3) . . . . ?
C7 C10 C19 N1 166.2(2) . . . . ?
C11 C10 C19 N1 38.5(2) . . . . ?
C7 C10 C19 C20 43.0(3) . . . . ?
C11 C10 C19 C20 -84.6(3) . . . . ?
C4 C7 C8 C9 60.8(3) . . . . ?
C10 C7 C8 C9 -174.0(2) . . . . ?
C27 C26 C31 C30 -2.2(4) . . . . ?
S1 C26 C31 C30 171.3(2) . . . . ?
C30 C29 C28 C27 -1.6(4) . . . . ?
C32 C29 C28 C27 176.8(3) . . . . ?
C26 C27 C28 C29 -0.5(4) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C16 C15 C14 C13 -0.9(4) . . . . ?
C25 C20 C21 C22 1.2(4) . . . . ?
C19 C20 C21 C22 177.9(3) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C12 C17 C16 C15 0.5(4) . . . . ?
C5 C4 C3 C2 -0.5(4) . . . . ?
C7 C4 C3 C2 -179.8(3) . . . . ?
C21 C20 C25 C24 -1.4(4) . . . . ?
C19 C20 C25 C24 -178.1(3) . . . . ?
C26 C31 C30 C29 0.1(4) . . . . ?
C28 C29 C30 C31 1.8(4) . . . . ?
C32 C29 C30 C31 -176.7(3) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C7 C4 C5 C6 179.3(3) . . . . ?
C1 C6 C5 C4 -0.3(5) . . . . ?
C4 C3 C2 C1 1.3(5) . . . . ?
C3 C2 C1 C6 -1.6(5) . . . . ?
C5 C6 C1 C2 1.1(5) . . . . ?
C24 C23 C22 C21 -0.1(6) . . . . ?
C20 C21 C22 C23 -0.5(5) . . . . ?
C22 C23 C24 C25 0.0(6) . . . . ?
C20 C25 C24 C23 0.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.032