Supplementary Material for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177

_publ_section_title              
;N-Heterocyclic carbene catalysed b-lactam synthesis
;
loop_
_publ_author_name
A.D.Smith
C.D.Campbell
N.Duguet
A.Slawin
_publ_contact_author_name        'Andrew D Smith'
_publ_contact_author_email       ADS10@ST-ANDREWS.AC.UK
# Attachment '5.cif'

data_5
_database_code_depnum_ccdc_archive 'CCDC 671783'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H23 N O3 S'
_chemical_formula_sum            'C28 H23 N O3 S'
_chemical_formula_weight         453.53

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   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                   6.6262(18)
_cell_length_b                   16.496(5)
_cell_length_c                   21.207(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2318.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    7429
_cell_measurement_theta_min      3.1288
_cell_measurement_theta_max      28.3018

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.1500
_exptl_crystal_size_mid          0.0800
_exptl_crystal_size_min          0.0800
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9268
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14524
_diffrn_reflns_av_R_equivalents  0.0820
_diffrn_reflns_av_sigmaI/netI    0.0752
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         25.33
_reflns_number_total             4181
_reflns_number_gt                3433
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0876P)^2^+0.0000P] 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   -0.15(13)
_refine_ls_number_reflns         4181
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.1741
_refine_ls_wR_factor_gt          0.1620
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.45060(14) 0.46468(6) 0.75215(4) 0.0342(3) Uani 1 1 d . . .
O4 O 0.5566(4) 0.52434(15) 0.78809(10) 0.0381(6) Uani 1 1 d . . .
O2 O 0.7574(4) 0.55800(16) 0.64977(13) 0.0430(7) Uani 1 1 d . . .
O3 O 0.2446(4) 0.44570(15) 0.76542(12) 0.0389(6) Uani 1 1 d . . .
N1 N 0.4470(4) 0.49718(17) 0.67765(13) 0.0303(7) Uani 1 1 d . . .
C2 C 0.5839(6) 0.5397(2) 0.64075(16) 0.0329(8) Uani 1 1 d . . .
C3 C 0.4263(6) 0.5510(2) 0.58807(16) 0.0331(8) Uani 1 1 d . . .
C4 C 0.2821(6) 0.4949(2) 0.62966(16) 0.0301(8) Uani 1 1 d . . .
H4A H 0.1591 0.5246 0.6442 0.036 Uiso 1 1 calc R . .
C5 C 0.5922(5) 0.3753(2) 0.75091(16) 0.0327(8) Uani 1 1 d . . .
C6 C 0.5013(6) 0.3015(2) 0.73364(18) 0.0393(9) Uani 1 1 d . . .
H6A H 0.3624 0.2995 0.7227 0.047 Uiso 1 1 calc R . .
C7 C 0.6163(7) 0.2325(2) 0.73287(18) 0.0400(9) Uani 1 1 d . . .
H7A H 0.5551 0.1828 0.7210 0.048 Uiso 1 1 calc R . .
C8 C 0.8172(6) 0.2329(2) 0.74873(18) 0.0385(9) Uani 1 1 d . . .
C9 C 0.9070(6) 0.3063(2) 0.76634(18) 0.0404(9) Uani 1 1 d . . .
H9A H 1.0456 0.3075 0.7777 0.048 Uiso 1 1 calc R . .
C10 C 0.7949(6) 0.3772(2) 0.76728(17) 0.0369(9) Uani 1 1 d . . .
H10A H 0.8565 0.4270 0.7791 0.044 Uiso 1 1 calc R . .
C11 C 0.9459(6) 0.1572(2) 0.7475(2) 0.0462(10) Uani 1 1 d . . .
H11A H 1.0570 0.1645 0.7175 0.069 Uiso 1 1 calc R . .
H11B H 0.8632 0.1109 0.7344 0.069 Uiso 1 1 calc R . .
H11C H 1.0009 0.1471 0.7897 0.069 Uiso 1 1 calc R . .
C12 C 0.3556(6) 0.6401(2) 0.58582(17) 0.0346(9) Uani 1 1 d . . .
C13 C 0.4941(6) 0.7026(2) 0.59393(17) 0.0409(10) Uani 1 1 d . . .
H13A H 0.6315 0.6907 0.6027 0.049 Uiso 1 1 calc R . .
C14 C 0.4295(8) 0.7832(2) 0.58906(19) 0.0504(11) Uani 1 1 d . . .
H14A H 0.5242 0.8259 0.5943 0.060 Uiso 1 1 calc R . .
C15 C 0.2316(8) 0.8014(3) 0.57678(18) 0.0495(12) Uani 1 1 d . . .
H15A H 0.1896 0.8563 0.5741 0.059 Uiso 1 1 calc R . .
C16 C 0.0932(8) 0.7400(3) 0.56826(19) 0.0471(11) Uani 1 1 d . . .
H16A H -0.0432 0.7527 0.5586 0.056 Uiso 1 1 calc R . .
C17 C 0.1529(7) 0.6591(3) 0.57370(18) 0.0411(10) Uani 1 1 d . . .
H17A H 0.0562 0.6169 0.5692 0.049 Uiso 1 1 calc R . .
C18 C 0.4846(6) 0.5220(2) 0.52239(16) 0.0346(9) Uani 1 1 d . . .
C19 C 0.6820(6) 0.5020(2) 0.50735(18) 0.0384(9) Uani 1 1 d . . .
H19A H 0.7847 0.5063 0.5384 0.046 Uiso 1 1 calc R . .
C20 C 0.7303(7) 0.4755(2) 0.44670(18) 0.0428(10) Uani 1 1 d . . .
H20A H 0.8656 0.4611 0.4369 0.051 Uiso 1 1 calc R . .
C21 C 0.5843(7) 0.4700(2) 0.40118(19) 0.0425(9) Uani 1 1 d . . .
H21A H 0.6187 0.4528 0.3598 0.051 Uiso 1 1 calc R . .
C22 C 0.3874(7) 0.4895(3) 0.41551(19) 0.0494(11) Uani 1 1 d . . .
H22A H 0.2857 0.4852 0.3841 0.059 Uiso 1 1 calc R . .
C23 C 0.3373(6) 0.5155(2) 0.47590(18) 0.0419(10) Uani 1 1 d . . .
H23A H 0.2013 0.5290 0.4855 0.050 Uiso 1 1 calc R . .
C24 C 0.2334(6) 0.4106(2) 0.60754(16) 0.0306(8) Uani 1 1 d . . .
C25 C 0.3796(6) 0.3560(2) 0.58643(17) 0.0386(9) Uani 1 1 d . . .
H25A H 0.5164 0.3729 0.5838 0.046 Uiso 1 1 calc R . .
C26 C 0.3288(7) 0.2779(3) 0.56933(19) 0.0454(11) Uani 1 1 d . . .
H26A H 0.4301 0.2414 0.5552 0.055 Uiso 1 1 calc R . .
C27 C 0.1269(8) 0.2524(2) 0.57295(19) 0.0470(11) Uani 1 1 d . . .
H27A H 0.0910 0.1987 0.5613 0.056 Uiso 1 1 calc R . .
C28 C -0.0174(7) 0.3054(3) 0.5934(2) 0.0468(10) Uani 1 1 d . . .
H28A H -0.1544 0.2886 0.5953 0.056 Uiso 1 1 calc R . .
C29 C 0.0344(6) 0.3834(2) 0.61117(17) 0.0363(9) Uani 1 1 d . . .
H29A H -0.0674 0.4191 0.6261 0.044 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 0.0344(5) 0.0386(5) 0.0297(5) 0.0004(4) -0.0009(4) 0.0020(4)
O4 0.0415(15) 0.0399(15) 0.0329(14) -0.0056(10) -0.0128(11) 0.0032(13)
O2 0.0279(15) 0.0571(17) 0.0439(15) -0.0007(12) -0.0033(12) -0.0066(13)
O3 0.0315(14) 0.0480(16) 0.0373(14) 0.0005(11) 0.0063(12) 0.0033(12)
N1 0.0261(15) 0.0367(16) 0.0282(15) 0.0071(12) -0.0029(12) -0.0031(14)
C2 0.031(2) 0.0328(19) 0.034(2) -0.0026(15) -0.0008(15) 0.0034(17)
C3 0.030(2) 0.037(2) 0.033(2) 0.0007(15) -0.0011(16) -0.0060(16)
C4 0.0296(19) 0.0325(19) 0.0280(18) 0.0030(14) -0.0005(15) -0.0001(16)
C5 0.0289(18) 0.035(2) 0.034(2) 0.0004(15) 0.0009(17) 0.0054(15)
C6 0.039(2) 0.036(2) 0.043(2) 0.0014(17) -0.0014(18) -0.0012(18)
C7 0.047(3) 0.036(2) 0.038(2) 0.0005(17) 0.0013(19) -0.0045(18)
C8 0.043(2) 0.037(2) 0.035(2) 0.0041(17) 0.0027(19) 0.0042(17)
C9 0.035(2) 0.045(2) 0.041(2) 0.0013(17) 0.0020(18) 0.0066(19)
C10 0.032(2) 0.046(2) 0.033(2) 0.0019(16) 0.0018(16) -0.0048(18)
C11 0.048(2) 0.038(2) 0.052(3) 0.0047(17) 0.012(2) 0.0074(19)
C12 0.042(2) 0.033(2) 0.030(2) 0.0008(16) 0.0059(17) 0.0008(17)
C13 0.044(3) 0.046(2) 0.033(2) -0.0018(17) 0.0018(17) -0.0067(19)
C14 0.071(3) 0.036(2) 0.044(2) 0.0025(17) 0.014(2) -0.004(2)
C15 0.074(3) 0.037(2) 0.038(2) 0.0016(17) 0.012(2) 0.006(2)
C16 0.050(3) 0.049(2) 0.042(2) 0.0071(18) 0.004(2) 0.013(2)
C17 0.046(3) 0.041(2) 0.037(2) 0.0018(17) -0.0038(18) 0.0026(19)
C18 0.038(2) 0.033(2) 0.0326(19) 0.0006(15) 0.0049(16) -0.0021(17)
C19 0.042(2) 0.037(2) 0.036(2) -0.0004(16) 0.0023(17) -0.0024(19)
C20 0.044(2) 0.048(2) 0.037(2) -0.0051(18) 0.0119(18) -0.004(2)
C21 0.055(3) 0.035(2) 0.038(2) -0.0010(16) 0.0120(19) 0.002(2)
C22 0.060(3) 0.056(3) 0.033(2) -0.0004(18) -0.005(2) -0.001(2)
C23 0.037(2) 0.055(3) 0.034(2) -0.0005(18) -0.0025(17) 0.0002(19)
C24 0.032(2) 0.0309(19) 0.0289(19) -0.0011(14) -0.0022(16) -0.0015(16)
C25 0.037(2) 0.042(2) 0.037(2) -0.0003(17) 0.0006(17) 0.0022(18)
C26 0.055(3) 0.039(2) 0.043(2) -0.0014(18) 0.005(2) 0.002(2)
C27 0.064(3) 0.033(2) 0.044(2) -0.0015(17) -0.005(2) -0.006(2)
C28 0.037(2) 0.048(2) 0.055(3) 0.001(2) -0.0028(19) -0.008(2)
C29 0.036(2) 0.039(2) 0.034(2) -0.0006(15) -0.0090(17) -0.0010(18)

_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 1.428(3) . ?
S1 O4 1.429(3) . ?
S1 N1 1.669(3) . ?
S1 C5 1.748(4) . ?
O2 C2 1.203(4) . ?
N1 C2 1.388(5) . ?
N1 C4 1.493(4) . ?
C2 C3 1.541(5) . ?
C3 C18 1.523(5) . ?
C3 C12 1.543(5) . ?
C3 C4 1.596(5) . ?
C4 C24 1.503(5) . ?
C4 H4A 1.0000 . ?
C5 C10 1.387(5) . ?
C5 C6 1.406(5) . ?
C6 C7 1.369(5) . ?
C6 H6A 0.9500 . ?
C7 C8 1.373(6) . ?
C7 H7A 0.9500 . ?
C8 C9 1.399(5) . ?
C8 C11 1.513(5) . ?
C9 C10 1.386(5) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.392(5) . ?
C12 C17 1.403(6) . ?
C13 C14 1.401(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.370(7) . ?
C14 H14A 0.9500 . ?
C15 C16 1.378(6) . ?
C15 H15A 0.9500 . ?
C16 C17 1.396(6) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 C19 1.386(5) . ?
C18 C23 1.391(5) . ?
C19 C20 1.396(5) . ?
C19 H19A 0.9500 . ?
C20 C21 1.370(6) . ?
C20 H20A 0.9500 . ?
C21 C22 1.378(7) . ?
C21 H21A 0.9500 . ?
C22 C23 1.391(6) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
C24 C29 1.394(5) . ?
C24 C25 1.397(5) . ?
C25 C26 1.381(6) . ?
C25 H25A 0.9500 . ?
C26 C27 1.404(6) . ?
C26 H26A 0.9500 . ?
C27 C28 1.366(6) . ?
C27 H27A 0.9500 . ?
C28 C29 1.385(5) . ?
C28 H28A 0.9500 . ?
C29 H29A 0.9500 . ?

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 121.03(17) . . ?
O3 S1 N1 104.08(15) . . ?
O4 S1 N1 106.90(15) . . ?
O3 S1 C5 109.33(16) . . ?
O4 S1 C5 108.97(16) . . ?
N1 S1 C5 105.34(15) . . ?
C2 N1 C4 96.1(2) . . ?
C2 N1 S1 133.4(2) . . ?
C4 N1 S1 130.4(2) . . ?
O2 C2 N1 131.4(3) . . ?
O2 C2 C3 137.1(3) . . ?
N1 C2 C3 91.5(3) . . ?
C18 C3 C2 117.0(3) . . ?
C18 C3 C12 110.4(3) . . ?
C2 C3 C12 110.1(3) . . ?
C18 C3 C4 118.4(3) . . ?
C2 C3 C4 86.3(2) . . ?
C12 C3 C4 112.8(3) . . ?
N1 C4 C24 113.1(3) . . ?
N1 C4 C3 85.7(2) . . ?
C24 C4 C3 119.5(3) . . ?
N1 C4 H4A 112.0 . . ?
C24 C4 H4A 112.0 . . ?
C3 C4 H4A 112.0 . . ?
C10 C5 C6 120.0(3) . . ?
C10 C5 S1 119.7(3) . . ?
C6 C5 S1 120.3(3) . . ?
C7 C6 C5 118.9(3) . . ?
C7 C6 H6A 120.6 . . ?
C5 C6 H6A 120.6 . . ?
C6 C7 C8 122.2(4) . . ?
C6 C7 H7A 118.9 . . ?
C8 C7 H7A 118.9 . . ?
C7 C8 C9 118.8(3) . . ?
C7 C8 C11 122.6(4) . . ?
C9 C8 C11 118.7(3) . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C9 C10 C5 119.7(4) . . ?
C9 C10 H10A 120.2 . . ?
C5 C10 H10A 120.2 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 119.2(4) . . ?
C13 C12 C3 120.1(4) . . ?
C17 C12 C3 120.6(3) . . ?
C12 C13 C14 119.6(4) . . ?
C12 C13 H13A 120.2 . . ?
C14 C13 H13A 120.2 . . ?
C15 C14 C13 120.9(4) . . ?
C15 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C15 C16 C17 120.2(4) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C16 C17 C12 120.0(4) . . ?
C16 C17 H17A 120.0 . . ?
C12 C17 H17A 120.0 . . ?
C19 C18 C23 118.7(3) . . ?
C19 C18 C3 121.6(3) . . ?
C23 C18 C3 119.6(3) . . ?
C18 C19 C20 120.2(4) . . ?
C18 C19 H19A 119.9 . . ?
C20 C19 H19A 119.9 . . ?
C21 C20 C19 120.5(4) . . ?
C21 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
C20 C21 C22 119.9(4) . . ?
C20 C21 H21A 120.1 . . ?
C22 C21 H21A 120.1 . . ?
C21 C22 C23 120.1(4) . . ?
C21 C22 H22A 120.0 . . ?
C23 C22 H22A 120.0 . . ?
C22 C23 C18 120.6(4) . . ?
C22 C23 H23A 119.7 . . ?
C18 C23 H23A 119.7 . . ?
C29 C24 C25 117.8(3) . . ?
C29 C24 C4 118.9(3) . . ?
C25 C24 C4 123.2(3) . . ?
C26 C25 C24 121.1(4) . . ?
C26 C25 H25A 119.4 . . ?
C24 C25 H25A 119.4 . . ?
C25 C26 C27 119.8(4) . . ?
C25 C26 H26A 120.1 . . ?
C27 C26 H26A 120.1 . . ?
C28 C27 C26 119.5(4) . . ?
C28 C27 H27A 120.3 . . ?
C26 C27 H27A 120.3 . . ?
C27 C28 C29 120.5(4) . . ?
C27 C28 H28A 119.7 . . ?
C29 C28 H28A 119.7 . . ?
C28 C29 C24 121.2(4) . . ?
C28 C29 H29A 119.4 . . ?
C24 C29 H29A 119.4 . . ?

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 N1 C2 164.4(3) . . . . ?
O4 S1 N1 C2 35.2(4) . . . . ?
C5 S1 N1 C2 -80.6(4) . . . . ?
O3 S1 N1 C4 -10.0(3) . . . . ?
O4 S1 N1 C4 -139.2(3) . . . . ?
C5 S1 N1 C4 105.0(3) . . . . ?
C4 N1 C2 O2 -174.5(4) . . . . ?
S1 N1 C2 O2 9.8(6) . . . . ?
C4 N1 C2 C3 5.2(3) . . . . ?
S1 N1 C2 C3 -170.5(3) . . . . ?
O2 C2 C3 C18 54.7(6) . . . . ?
N1 C2 C3 C18 -124.9(3) . . . . ?
O2 C2 C3 C12 -72.3(5) . . . . ?
N1 C2 C3 C12 108.1(3) . . . . ?
O2 C2 C3 C4 174.8(5) . . . . ?
N1 C2 C3 C4 -4.8(3) . . . . ?
C2 N1 C4 C24 115.3(3) . . . . ?
S1 N1 C4 C24 -68.8(4) . . . . ?
C2 N1 C4 C3 -5.0(3) . . . . ?
S1 N1 C4 C3 170.9(3) . . . . ?
C18 C3 C4 N1 123.3(3) . . . . ?
C2 C3 C4 N1 4.5(2) . . . . ?
C12 C3 C4 N1 -105.7(3) . . . . ?
C18 C3 C4 C24 9.1(5) . . . . ?
C2 C3 C4 C24 -109.7(3) . . . . ?
C12 C3 C4 C24 140.1(3) . . . . ?
O3 S1 C5 C10 -151.0(3) . . . . ?
O4 S1 C5 C10 -16.7(3) . . . . ?
N1 S1 C5 C10 97.7(3) . . . . ?
O3 S1 C5 C6 28.8(4) . . . . ?
O4 S1 C5 C6 163.1(3) . . . . ?
N1 S1 C5 C6 -82.6(3) . . . . ?
C10 C5 C6 C7 -0.5(6) . . . . ?
S1 C5 C6 C7 179.7(3) . . . . ?
C5 C6 C7 C8 0.4(6) . . . . ?
C6 C7 C8 C9 0.1(6) . . . . ?
C6 C7 C8 C11 -179.5(4) . . . . ?
C7 C8 C9 C10 -0.4(6) . . . . ?
C11 C8 C9 C10 179.1(3) . . . . ?
C8 C9 C10 C5 0.3(6) . . . . ?
C6 C5 C10 C9 0.2(6) . . . . ?
S1 C5 C10 C9 179.9(3) . . . . ?
C18 C3 C12 C13 -90.3(4) . . . . ?
C2 C3 C12 C13 40.3(4) . . . . ?
C4 C3 C12 C13 134.8(3) . . . . ?
C18 C3 C12 C17 87.7(4) . . . . ?
C2 C3 C12 C17 -141.6(4) . . . . ?
C4 C3 C12 C17 -47.1(5) . . . . ?
C17 C12 C13 C14 -0.8(6) . . . . ?
C3 C12 C13 C14 177.2(3) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
C13 C14 C15 C16 -0.8(6) . . . . ?
C14 C15 C16 C17 1.7(6) . . . . ?
C15 C16 C17 C12 -2.1(6) . . . . ?
C13 C12 C17 C16 1.7(6) . . . . ?
C3 C12 C17 C16 -176.4(3) . . . . ?
C2 C3 C18 C19 -12.9(5) . . . . ?
C12 C3 C18 C19 113.9(4) . . . . ?
C4 C3 C18 C19 -114.0(4) . . . . ?
C2 C3 C18 C23 167.4(3) . . . . ?
C12 C3 C18 C23 -65.8(4) . . . . ?
C4 C3 C18 C23 66.3(5) . . . . ?
C23 C18 C19 C20 -0.4(6) . . . . ?
C3 C18 C19 C20 179.9(3) . . . . ?
C18 C19 C20 C21 0.9(6) . . . . ?
C19 C20 C21 C22 -1.1(6) . . . . ?
C20 C21 C22 C23 0.7(7) . . . . ?
C21 C22 C23 C18 -0.1(6) . . . . ?
C19 C18 C23 C22 0.0(6) . . . . ?
C3 C18 C23 C22 179.7(4) . . . . ?
N1 C4 C24 C29 125.9(3) . . . . ?
C3 C4 C24 C29 -135.7(4) . . . . ?
N1 C4 C24 C25 -50.6(4) . . . . ?
C3 C4 C24 C25 47.9(5) . . . . ?
C29 C24 C25 C26 0.4(5) . . . . ?
C4 C24 C25 C26 176.9(3) . . . . ?
C24 C25 C26 C27 0.1(6) . . . . ?
C25 C26 C27 C28 0.1(6) . . . . ?
C26 C27 C28 C29 -0.8(6) . . . . ?
C27 C28 C29 C24 1.4(6) . . . . ?
C25 C24 C29 C28 -1.2(5) . . . . ?
C4 C24 C29 C28 -177.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.072