# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2006

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        J.Clayden
_publ_contact_author_address     
;
Department of Chemistry
University of Manchester
Oxford Road
MANCHESTER
M13 9PL
UNITED KINGDOM
;

_publ_contact_author_email       J.P.CLAYDEN@MAN.AC.UK

_publ_section_title              
;
Achieving conformational control over C-C, C-N and C-O
bonds in biaryls, N,N'-diarylureas and diaryl ethers: advantages of a
relay axis.
;
loop_
_publ_author_name
'J. Clayden'
'Mark S. Betson'
'Ann Bracegirdle'
'Madeleine Helliwell'
'Andrew Lund'
;
M.Pickworth
;
'Tim Snape'
'Christopher P. Worrall'

# Attachment '4x s1824_dc corrected.cif'

data_s1824_dc
_database_code_depnum_ccdc_archive 'CCDC 623108'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;

_publ_section_exptl_refinement   
;
The structure was solved by direct methods.
There is solvent atom assumed to be water at
0.25 occupancy.
The non-H atoms were refined anisotropically, except
for the solvent water.
H atoms were included in calculated positions, except those of the
solvent which were not included.

;

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24.50 N2 O2.25 S'
_chemical_formula_weight         397.01

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   C2

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

_cell_length_a                   24.932(6)
_cell_length_b                   8.345(3)
_cell_length_c                   10.856(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.65(2)
_cell_angle_gamma                90.00
_cell_volume                     2140.3(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1230
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      25.03

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             842
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6959
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_sigmaI/netI    0.1408
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2700
_reflns_number_gt                1230
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrysalisCCD
_computing_cell_refinement       CrysalisCCD
_computing_data_reduction        CrysalisRED
_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^)+(0.0322P)^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   0.01(11)
_refine_ls_number_reflns         2700
_refine_ls_number_parameters     259
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0761
_refine_ls_goodness_of_fit_ref   0.802
_refine_ls_restrained_S_all      0.802
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.001

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
O1S O 0.0000 0.2240(15) 0.0000 0.123(4) Uiso 0.50 2 d SP . .
S1 S 0.07603(6) 0.16430(15) 0.81449(12) 0.0674(4) Uani 1 1 d . . .
O1 O 0.02067(15) 0.0766(4) 0.7716(3) 0.0833(11) Uani 1 1 d . . .
O2 O 0.22016(16) 0.3104(4) 1.0177(3) 0.0858(12) Uani 1 1 d . . .
N1 N 0.15731(17) 0.4530(4) 0.8587(4) 0.0600(11) Uani 1 1 d . . .
N2 N 0.14404(16) 0.4274(5) 1.0600(4) 0.0553(11) Uani 1 1 d . . .
C1 C 0.0586(2) 0.3705(5) 0.7617(4) 0.0521(13) Uani 1 1 d . . .
C2 C 0.09858(19) 0.4889(6) 0.7936(4) 0.0451(12) Uani 1 1 d . . .
C3 C 0.0820(2) 0.6455(7) 0.7541(4) 0.0580(13) Uani 1 1 d . . .
H3 H 0.1083 0.7284 0.7738 0.070 Uiso 1 1 calc R . .
C4 C 0.0255(2) 0.6758(7) 0.6849(4) 0.0595(13) Uani 1 1 d . . .
H4 H 0.0147 0.7801 0.6581 0.071 Uiso 1 1 calc R . .
C5 C -0.0151(2) 0.5576(7) 0.6544(4) 0.0595(14) Uani 1 1 d . . .
C6 C 0.0025(2) 0.4031(6) 0.6966(5) 0.0587(14) Uani 1 1 d . . .
H6 H -0.0240 0.3208 0.6807 0.070 Uiso 1 1 calc R . .
C7 C 0.1963(2) 0.4716(7) 0.7845(5) 0.0818(18) Uani 1 1 d . . .
H7A H 0.2325 0.4279 0.8331 0.123 Uiso 1 1 calc R . .
H7B H 0.2004 0.5833 0.7684 0.123 Uiso 1 1 calc R . .
H7C H 0.1817 0.4159 0.7033 0.123 Uiso 1 1 calc R . .
C8 C 0.1764(2) 0.3922(6) 0.9816(5) 0.0583(14) Uani 1 1 d . . .
C9 C 0.1510(2) 0.3238(6) 1.1712(5) 0.0743(16) Uani 1 1 d . . .
H9A H 0.1667 0.2232 1.1569 0.111 Uiso 1 1 calc R . .
H9B H 0.1148 0.3060 1.1827 0.111 Uiso 1 1 calc R . .
H9C H 0.1760 0.3737 1.2477 0.111 Uiso 1 1 calc R . .
C10 C 0.1270(2) 0.5864(6) 1.0712(4) 0.0510(12) Uani 1 1 d . . .
C11 C 0.1602(2) 0.7164(6) 1.0613(4) 0.0588(15) Uani 1 1 d . . .
H11 H 0.1942 0.6986 1.0449 0.071 Uiso 1 1 calc R . .
C12 C 0.1437(2) 0.8711(7) 1.0752(5) 0.0696(17) Uani 1 1 d . . .
H12 H 0.1662 0.9568 1.0669 0.084 Uiso 1 1 calc R . .
C13 C 0.0940(2) 0.8989(7) 1.1015(5) 0.0659(15) Uani 1 1 d . . .
H13 H 0.0828 1.0029 1.1123 0.079 Uiso 1 1 calc R . .
C14 C 0.0615(2) 0.7715(8) 1.1115(5) 0.0693(16) Uani 1 1 d . . .
H14 H 0.0281 0.7900 1.1300 0.083 Uiso 1 1 calc R . .
C15 C 0.0765(2) 0.6170(6) 1.0953(4) 0.0640(15) Uani 1 1 d . . .
H15 H 0.0529 0.5327 1.1003 0.077 Uiso 1 1 calc R . .
C16 C -0.0766(2) 0.5932(6) 0.5807(4) 0.0782(17) Uani 1 1 d . . .
H16A H -0.0834 0.5772 0.4894 0.117 Uiso 1 1 calc R . .
H16B H -0.0849 0.7023 0.5960 0.117 Uiso 1 1 calc R . .
H16C H -0.1004 0.5226 0.6100 0.117 Uiso 1 1 calc R . .
C17 C 0.1127(2) 0.1097(5) 0.7042(5) 0.0552(14) Uani 1 1 d . . .
C18 C 0.0887(2) 0.1093(6) 0.5732(5) 0.0788(18) Uani 1 1 d . . .
H18 H 0.0519 0.1465 0.5373 0.095 Uiso 1 1 calc R . .
C19 C 0.1170(3) 0.0561(7) 0.4922(5) 0.092(2) Uani 1 1 d . . .
H19 H 0.0986 0.0571 0.4030 0.110 Uiso 1 1 calc R . .
C20 C 0.1716(3) 0.0012(7) 0.5389(6) 0.090(2) Uani 1 1 d . . .
C21 C 0.1954(2) 0.0002(8) 0.6737(7) 0.103(2) Uani 1 1 d . . .
H21 H 0.2322 -0.0375 0.7102 0.124 Uiso 1 1 calc R . .
C22 C 0.1667(3) 0.0527(7) 0.7544(5) 0.0884(19) Uani 1 1 d . . .
H22 H 0.1840 0.0495 0.8440 0.106 Uiso 1 1 calc R . .
C23 C 0.2038(3) -0.0567(9) 0.4493(7) 0.140(3) Uani 1 1 d . . .
H23A H 0.1777 -0.0737 0.3637 0.210 Uiso 1 1 calc R . .
H23B H 0.2228 -0.1554 0.4822 0.210 Uiso 1 1 calc R . .
H23C H 0.2312 0.0226 0.4458 0.210 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 0.0797(11) 0.0542(8) 0.0641(8) 0.0004(8) 0.0171(7) 0.0070(9)
O1 0.080(3) 0.062(2) 0.109(3) -0.001(2) 0.031(2) -0.016(2)
O2 0.068(3) 0.104(3) 0.072(3) -0.004(2) 0.004(2) 0.018(2)
N1 0.052(3) 0.067(3) 0.058(3) -0.011(2) 0.012(2) 0.000(2)
N2 0.063(3) 0.062(3) 0.040(3) 0.001(2) 0.015(2) -0.006(2)
C1 0.057(4) 0.048(3) 0.052(3) -0.006(2) 0.020(3) -0.006(3)
C2 0.047(3) 0.056(3) 0.037(3) -0.008(2) 0.018(2) 0.004(3)
C3 0.058(3) 0.061(3) 0.053(3) -0.002(3) 0.015(3) -0.013(3)
C4 0.076(4) 0.057(3) 0.048(3) 0.012(3) 0.024(3) 0.014(3)
C5 0.066(4) 0.061(3) 0.046(3) 0.000(3) 0.009(3) 0.001(3)
C6 0.048(3) 0.065(4) 0.057(3) -0.005(3) 0.008(3) -0.002(3)
C7 0.052(3) 0.124(5) 0.074(4) 0.000(4) 0.027(3) 0.005(3)
C8 0.059(4) 0.066(4) 0.049(4) -0.009(3) 0.015(3) 0.004(3)
C9 0.084(4) 0.067(4) 0.072(4) 0.001(3) 0.025(3) -0.011(3)
C10 0.055(3) 0.051(3) 0.048(3) -0.006(3) 0.019(3) 0.005(3)
C11 0.053(3) 0.074(4) 0.048(3) -0.013(3) 0.013(3) -0.011(3)
C12 0.077(4) 0.058(4) 0.063(4) -0.002(3) 0.008(3) -0.014(3)
C13 0.074(4) 0.064(4) 0.063(4) -0.006(3) 0.027(3) 0.008(4)
C14 0.062(4) 0.092(5) 0.058(4) 0.004(3) 0.025(3) 0.011(4)
C15 0.063(4) 0.062(4) 0.064(4) 0.004(3) 0.016(3) 0.002(3)
C16 0.062(4) 0.108(5) 0.064(3) 0.013(3) 0.019(3) 0.013(3)
C17 0.059(3) 0.042(3) 0.054(3) -0.004(2) 0.003(3) 0.008(2)
C18 0.078(4) 0.085(5) 0.054(4) -0.002(3) -0.006(3) 0.019(3)
C19 0.099(5) 0.107(5) 0.052(4) -0.018(4) 0.000(4) 0.020(4)
C20 0.086(5) 0.100(5) 0.072(5) -0.019(4) 0.008(4) 0.018(4)
C21 0.064(4) 0.149(6) 0.083(5) -0.025(4) 0.003(4) 0.038(4)
C22 0.082(4) 0.103(5) 0.059(4) -0.017(3) -0.008(4) 0.025(4)
C23 0.120(6) 0.183(8) 0.108(6) -0.044(5) 0.024(5) 0.049(6)

_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 1.499(3) . ?
S1 C17 1.782(5) . ?
S1 C1 1.822(5) . ?
O2 C8 1.240(5) . ?
N1 C8 1.364(6) . ?
N1 C2 1.439(5) . ?
N1 C7 1.455(6) . ?
N2 C8 1.378(6) . ?
N2 C10 1.411(6) . ?
N2 C9 1.450(5) . ?
C1 C2 1.367(6) . ?
C1 C6 1.377(6) . ?
C2 C3 1.396(6) . ?
C3 C4 1.391(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(6) . ?
C5 C16 1.516(6) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.388(6) . ?
C10 C11 1.391(6) . ?
C11 C12 1.378(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.355(6) . ?
C17 C22 1.367(6) . ?
C18 C19 1.364(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.392(7) . ?
C20 C23 1.524(8) . ?
C21 C22 1.369(7) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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 C17 106.6(2) . . ?
O1 S1 C1 105.1(2) . . ?
C17 S1 C1 98.8(2) . . ?
C8 N1 C2 122.7(4) . . ?
C8 N1 C7 119.7(4) . . ?
C2 N1 C7 117.4(4) . . ?
C8 N2 C10 120.4(4) . . ?
C8 N2 C9 116.7(5) . . ?
C10 N2 C9 116.6(4) . . ?
C2 C1 C6 121.7(4) . . ?
C2 C1 S1 121.4(4) . . ?
C6 C1 S1 116.7(4) . . ?
C1 C2 C3 118.6(4) . . ?
C1 C2 N1 121.2(4) . . ?
C3 C2 N1 120.1(4) . . ?
C4 C3 C2 119.0(5) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 122.7(5) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C4 C5 C6 117.1(5) . . ?
C4 C5 C16 121.9(5) . . ?
C6 C5 C16 120.9(5) . . ?
C1 C6 C5 120.8(5) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 N1 120.7(5) . . ?
O2 C8 N2 123.5(5) . . ?
N1 C8 N2 115.8(5) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.1(5) . . ?
C15 C10 N2 120.4(5) . . ?
C11 C10 N2 121.5(4) . . ?
C12 C11 C10 121.0(5) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.1(6) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 118.8(5) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 122.2(5) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C14 C15 C10 119.8(5) . . ?
C14 C15 H15 120.1 . . ?
C10 C15 H15 120.1 . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 117.7(5) . . ?
C18 C17 S1 123.9(4) . . ?
C22 C17 S1 118.2(4) . . ?
C17 C18 C19 122.2(5) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C18 C19 C20 121.8(6) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C19 C20 C21 115.4(6) . . ?
C19 C20 C23 122.3(6) . . ?
C21 C20 C23 122.3(6) . . ?
C22 C21 C20 122.5(6) . . ?
C22 C21 H21 118.8 . . ?
C20 C21 H21 118.8 . . ?
C17 C22 C21 120.4(5) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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 C1 C2 174.8(4) . . . . ?
C17 S1 C1 C2 -75.3(4) . . . . ?
O1 S1 C1 C6 -0.6(4) . . . . ?
C17 S1 C1 C6 109.3(4) . . . . ?
C6 C1 C2 C3 -2.5(6) . . . . ?
S1 C1 C2 C3 -177.7(3) . . . . ?
C6 C1 C2 N1 -178.4(4) . . . . ?
S1 C1 C2 N1 6.5(6) . . . . ?
C8 N1 C2 C1 -65.1(6) . . . . ?
C7 N1 C2 C1 110.1(5) . . . . ?
C8 N1 C2 C3 119.1(5) . . . . ?
C7 N1 C2 C3 -65.7(6) . . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
N1 C2 C3 C4 176.4(4) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
C3 C4 C5 C16 179.0(4) . . . . ?
C2 C1 C6 C5 3.6(7) . . . . ?
S1 C1 C6 C5 178.9(4) . . . . ?
C4 C5 C6 C1 -2.4(7) . . . . ?
C16 C5 C6 C1 178.9(4) . . . . ?
C2 N1 C8 O2 153.7(5) . . . . ?
C7 N1 C8 O2 -21.3(7) . . . . ?
C2 N1 C8 N2 -26.1(6) . . . . ?
C7 N1 C8 N2 158.8(4) . . . . ?
C10 N2 C8 O2 130.9(5) . . . . ?
C9 N2 C8 O2 -20.4(7) . . . . ?
C10 N2 C8 N1 -49.3(6) . . . . ?
C9 N2 C8 N1 159.4(4) . . . . ?
C8 N2 C10 C15 149.9(4) . . . . ?
C9 N2 C10 C15 -58.8(6) . . . . ?
C8 N2 C10 C11 -31.3(6) . . . . ?
C9 N2 C10 C11 119.9(5) . . . . ?
C15 C10 C11 C12 0.2(7) . . . . ?
N2 C10 C11 C12 -178.6(4) . . . . ?
C10 C11 C12 C13 1.0(7) . . . . ?
C11 C12 C13 C14 -0.9(8) . . . . ?
C12 C13 C14 C15 -0.6(8) . . . . ?
C13 C14 C15 C10 1.8(8) . . . . ?
C11 C10 C15 C14 -1.6(7) . . . . ?
N2 C10 C15 C14 177.2(4) . . . . ?
O1 S1 C17 C18 47.3(5) . . . . ?
C1 S1 C17 C18 -61.4(5) . . . . ?
O1 S1 C17 C22 -127.2(4) . . . . ?
C1 S1 C17 C22 124.1(4) . . . . ?
C22 C17 C18 C19 -0.7(8) . . . . ?
S1 C17 C18 C19 -175.3(4) . . . . ?
C17 C18 C19 C20 -0.6(10) . . . . ?
C18 C19 C20 C21 1.5(9) . . . . ?
C18 C19 C20 C23 -179.3(6) . . . . ?
C19 C20 C21 C22 -1.0(9) . . . . ?
C23 C20 C21 C22 179.7(6) . . . . ?
C18 C17 C22 C21 1.2(8) . . . . ?
S1 C17 C22 C21 176.1(5) . . . . ?
C20 C21 C22 C17 -0.4(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.035

# Attachment '5x s2305m.cif'

data_s2305m
_database_code_depnum_ccdc_archive 'CCDC 623109'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;

_publ_section_exptl_refinement   
;

The structure was solved by the direct methods.
All non-H atoms were refined anisotropically.
H atoms were included in calculated positions.

;

_publ_section_figure_captions    
;
ENTER FIGURE CAPTIONS
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H30 O3 S'
_chemical_formula_weight         374.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           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                   8.3358(11)
_cell_length_b                   12.2620(17)
_cell_length_c                   20.222(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.368(2)
_cell_angle_gamma                90.00
_cell_volume                     2044.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7926
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      26.92

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9170
_exptl_absorpt_correction_T_max  0.9328
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14180
_diffrn_reflns_av_R_equivalents  0.1272
_diffrn_reflns_av_sigmaI/netI    0.0678
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3606
_reflns_number_gt                3062
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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^)+(0.1009P)^2^+0.0562P] 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_number_reflns         3606
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1477
_refine_ls_wR_factor_gt          0.1430
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.16658(5) 1.00032(3) 0.32032(2) 0.02077(19) Uani 1 1 d . . .
O1 O 0.20899(14) 0.80034(10) 0.40289(6) 0.0205(3) Uani 1 1 d . . .
O2 O 0.51011(17) 0.53377(11) 0.36976(7) 0.0286(3) Uani 1 1 d . . .
O3 O 0.23552(16) 1.10503(10) 0.29739(7) 0.0276(3) Uani 1 1 d . . .
C1 C 0.3174(2) 0.89656(15) 0.31586(9) 0.0201(4) Uani 1 1 d . . .
C2 C 0.3237(2) 0.80651(15) 0.35886(9) 0.0194(4) Uani 1 1 d . . .
C3 C 0.4327(2) 0.72102(14) 0.35382(9) 0.0206(4) Uani 1 1 d . . .
C4 C 0.5362(2) 0.72864(15) 0.30551(9) 0.0234(4) Uani 1 1 d . . .
H4 H 0.6097 0.6710 0.3007 0.028 Uiso 1 1 calc R . .
C5 C 0.5328(2) 0.82016(16) 0.26413(9) 0.0245(4) Uani 1 1 d . . .
H5 H 0.6049 0.8242 0.2319 0.029 Uiso 1 1 calc R . .
C6 C 0.4259(2) 0.90494(16) 0.26941(9) 0.0238(4) Uani 1 1 d . . .
H6 H 0.4261 0.9678 0.2420 0.029 Uiso 1 1 calc R . .
C7 C 0.2604(2) 0.82052(14) 0.47139(9) 0.0200(4) Uani 1 1 d . . .
C8 C 0.1448(2) 0.80350(14) 0.51518(9) 0.0213(4) Uani 1 1 d . . .
C9 C 0.2012(2) 0.82278(16) 0.58325(9) 0.0261(4) Uani 1 1 d . . .
H9 H 0.1283 0.8122 0.6147 0.031 Uiso 1 1 calc R . .
C10 C 0.3589(2) 0.85663(16) 0.60666(10) 0.0284(5) Uani 1 1 d . . .
H10 H 0.3921 0.8677 0.6531 0.034 Uiso 1 1 calc R . .
C11 C 0.4671(2) 0.87398(16) 0.56178(10) 0.0283(5) Uani 1 1 d . . .
H11 H 0.5746 0.8977 0.5772 0.034 Uiso 1 1 calc R . .
C12 C 0.4165(2) 0.85630(15) 0.49371(9) 0.0241(4) Uani 1 1 d . . .
H12 H 0.4895 0.8689 0.4626 0.029 Uiso 1 1 calc R . .
C13 C -0.0329(2) 0.77118(16) 0.49058(10) 0.0241(4) Uani 1 1 d . . .
C14 C -0.1294(2) 0.75300(18) 0.54953(10) 0.0332(5) Uani 1 1 d . . .
H14A H -0.2403 0.7306 0.5322 0.050 Uiso 1 1 calc R . .
H14B H -0.1321 0.8210 0.5748 0.050 Uiso 1 1 calc R . .
H14C H -0.0767 0.6959 0.5790 0.050 Uiso 1 1 calc R . .
C15 C -0.1181(2) 0.86415(17) 0.44715(10) 0.0288(5) Uani 1 1 d . . .
H15A H -0.0549 0.8821 0.4114 0.043 Uiso 1 1 calc R . .
H15B H -0.1264 0.9287 0.4750 0.043 Uiso 1 1 calc R . .
H15C H -0.2270 0.8405 0.4275 0.043 Uiso 1 1 calc R . .
C16 C -0.0408(3) 0.66378(18) 0.45027(11) 0.0335(5) Uani 1 1 d . . .
H16A H 0.0102 0.6745 0.4100 0.050 Uiso 1 1 calc R . .
H16B H -0.1543 0.6424 0.4374 0.050 Uiso 1 1 calc R . .
H16C H 0.0168 0.6063 0.4778 0.050 Uiso 1 1 calc R . .
C17 C 0.4387(2) 0.62338(14) 0.39983(9) 0.0234(4) Uani 1 1 d . . .
H17A H 0.5037 0.6410 0.4435 0.028 Uiso 1 1 calc R . .
H17B H 0.3277 0.6040 0.4076 0.028 Uiso 1 1 calc R . .
C18 C 0.5331(3) 0.44192(16) 0.41333(11) 0.0363(5) Uani 1 1 d . . .
H18A H 0.6085 0.4612 0.4534 0.054 Uiso 1 1 calc R . .
H18B H 0.5779 0.3812 0.3903 0.054 Uiso 1 1 calc R . .
H18C H 0.4288 0.4202 0.4262 0.054 Uiso 1 1 calc R . .
C19 C 0.0103(2) 0.95331(15) 0.24921(9) 0.0236(4) Uani 1 1 d . . .
C20 C -0.0257(2) 0.83230(16) 0.25625(10) 0.0276(5) Uani 1 1 d . . .
H20A H -0.1136 0.8106 0.2211 0.041 Uiso 1 1 calc R . .
H20B H -0.0584 0.8188 0.3002 0.041 Uiso 1 1 calc R . .
H20C H 0.0718 0.7897 0.2520 0.041 Uiso 1 1 calc R . .
C21 C -0.1388(2) 1.02325(17) 0.25656(12) 0.0345(5) Uani 1 1 d . . .
H21A H -0.1107 1.1006 0.2542 0.052 Uiso 1 1 calc R . .
H21B H -0.1743 1.0080 0.2997 0.052 Uiso 1 1 calc R . .
H21C H -0.2267 1.0058 0.2204 0.052 Uiso 1 1 calc R . .
C22 C 0.0724(3) 0.9780(2) 0.18340(11) 0.0383(5) Uani 1 1 d . . .
H22A H 0.1534 0.9234 0.1756 0.058 Uiso 1 1 calc R . .
H22B H 0.1218 1.0507 0.1857 0.058 Uiso 1 1 calc R . .
H22C H -0.0183 0.9758 0.1467 0.058 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 0.0224(3) 0.0225(3) 0.0180(3) -0.00047(17) 0.0050(2) 0.00117(16)
O1 0.0201(7) 0.0307(7) 0.0123(7) -0.0005(5) 0.0074(5) 0.0000(5)
O2 0.0433(8) 0.0267(7) 0.0182(7) 0.0025(6) 0.0129(6) 0.0090(6)
O3 0.0304(8) 0.0228(7) 0.0295(8) 0.0014(6) 0.0043(6) -0.0022(5)
C1 0.0215(9) 0.0235(9) 0.0159(9) -0.0014(7) 0.0046(7) -0.0005(7)
C2 0.0180(9) 0.0278(10) 0.0137(9) -0.0004(7) 0.0070(7) -0.0026(7)
C3 0.0227(9) 0.0249(9) 0.0148(9) -0.0009(7) 0.0050(7) -0.0015(7)
C4 0.0229(10) 0.0293(10) 0.0191(10) -0.0017(8) 0.0069(7) 0.0022(8)
C5 0.0235(10) 0.0330(10) 0.0193(10) -0.0002(8) 0.0107(8) -0.0015(8)
C6 0.0248(10) 0.0292(10) 0.0183(10) 0.0036(8) 0.0057(7) -0.0025(8)
C7 0.0251(10) 0.0215(9) 0.0136(9) -0.0001(7) 0.0036(7) 0.0034(7)
C8 0.0280(10) 0.0205(9) 0.0169(9) 0.0007(7) 0.0083(8) 0.0037(7)
C9 0.0349(11) 0.0300(10) 0.0153(10) -0.0001(8) 0.0097(8) 0.0052(8)
C10 0.0358(11) 0.0336(11) 0.0155(10) -0.0038(8) 0.0025(8) 0.0085(8)
C11 0.0261(10) 0.0323(11) 0.0260(11) -0.0073(8) 0.0015(8) 0.0028(8)
C12 0.0261(10) 0.0282(10) 0.0197(10) -0.0024(8) 0.0085(8) 0.0018(8)
C13 0.0263(10) 0.0272(10) 0.0213(10) -0.0018(8) 0.0122(8) -0.0015(8)
C14 0.0326(11) 0.0428(12) 0.0276(12) 0.0031(9) 0.0159(9) -0.0011(9)
C15 0.0241(10) 0.0401(12) 0.0234(11) 0.0017(9) 0.0077(8) 0.0012(8)
C16 0.0323(11) 0.0336(11) 0.0383(12) -0.0087(9) 0.0172(10) -0.0079(9)
C17 0.0273(10) 0.0266(10) 0.0183(10) 0.0000(8) 0.0098(8) 0.0035(8)
C18 0.0538(14) 0.0282(11) 0.0297(12) 0.0075(9) 0.0158(10) 0.0111(10)
C19 0.0243(10) 0.0263(10) 0.0200(10) 0.0017(7) 0.0024(8) -0.0010(8)
C20 0.0286(10) 0.0267(10) 0.0270(11) -0.0023(8) 0.0025(8) -0.0005(8)
C21 0.0292(11) 0.0279(10) 0.0441(14) -0.0027(9) -0.0023(10) 0.0019(9)
C22 0.0370(12) 0.0571(14) 0.0199(11) 0.0062(10) 0.0009(9) -0.0126(11)

_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 1.5070(13) . ?
S1 C1 1.8004(18) . ?
S1 C19 1.8847(19) . ?
O1 C2 1.400(2) . ?
O1 C7 1.411(2) . ?
O2 C18 1.426(2) . ?
O2 C17 1.427(2) . ?
C1 C6 1.399(2) . ?
C1 C2 1.402(3) . ?
C2 C3 1.400(3) . ?
C3 C4 1.398(2) . ?
C3 C17 1.513(2) . ?
C4 C5 1.398(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.385(3) . ?
C7 C8 1.416(2) . ?
C8 C9 1.408(3) . ?
C8 C13 1.544(3) . ?
C9 C10 1.394(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.397(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C16 1.545(3) . ?
C13 C15 1.547(3) . ?
C13 C14 1.548(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.525(3) . ?
C19 C22 1.527(3) . ?
C19 C21 1.535(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
O3 S1 C1 106.63(8) . . ?
O3 S1 C19 106.14(8) . . ?
C1 S1 C19 98.97(8) . . ?
C2 O1 C7 118.47(13) . . ?
C18 O2 C17 111.82(14) . . ?
C6 C1 C2 120.33(16) . . ?
C6 C1 S1 120.39(14) . . ?
C2 C1 S1 119.27(13) . . ?
C3 C2 O1 121.07(15) . . ?
C3 C2 C1 120.70(16) . . ?
O1 C2 C1 118.01(15) . . ?
C4 C3 C2 118.29(16) . . ?
C4 C3 C17 120.94(16) . . ?
C2 C3 C17 120.77(15) . . ?
C5 C4 C3 120.75(17) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 120.95(17) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 118.88(17) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
C12 C7 O1 120.82(16) . . ?
C12 C7 C8 122.38(17) . . ?
O1 C7 C8 116.80(16) . . ?
C9 C8 C7 115.20(17) . . ?
C9 C8 C13 121.75(17) . . ?
C7 C8 C13 123.00(16) . . ?
C10 C9 C8 123.10(18) . . ?
C10 C9 H9 118.5 . . ?
C8 C9 H9 118.5 . . ?
C11 C10 C9 119.65(18) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 119.33(18) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C11 120.32(17) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C8 C13 C16 110.71(15) . . ?
C8 C13 C15 109.47(16) . . ?
C16 C13 C15 110.35(17) . . ?
C8 C13 C14 111.73(16) . . ?
C16 C13 C14 107.26(16) . . ?
C15 C13 C14 107.24(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 C3 109.02(14) . . ?
O2 C17 H17A 109.9 . . ?
C3 C17 H17A 109.9 . . ?
O2 C17 H17B 109.9 . . ?
C3 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C22 111.77(17) . . ?
C20 C19 C21 111.19(16) . . ?
C22 C19 C21 110.82(17) . . ?
C20 C19 S1 110.48(13) . . ?
C22 C19 S1 108.66(13) . . ?
C21 C19 S1 103.58(13) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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 C1 C6 -28.46(17) . . . . ?
C19 S1 C1 C6 81.47(16) . . . . ?
O3 S1 C1 C2 152.37(15) . . . . ?
C19 S1 C1 C2 -97.70(16) . . . . ?
C7 O1 C2 C3 78.5(2) . . . . ?
C7 O1 C2 C1 -106.90(18) . . . . ?
C6 C1 C2 C3 -3.3(3) . . . . ?
S1 C1 C2 C3 175.91(14) . . . . ?
C6 C1 C2 O1 -177.93(15) . . . . ?
S1 C1 C2 O1 1.2(2) . . . . ?
O1 C2 C3 C4 175.39(15) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
O1 C2 C3 C17 -5.0(3) . . . . ?
C1 C2 C3 C17 -179.52(17) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C17 C3 C4 C5 -178.52(17) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 -1.7(3) . . . . ?
C2 C1 C6 C5 3.6(3) . . . . ?
S1 C1 C6 C5 -175.55(15) . . . . ?
C2 O1 C7 C12 6.4(2) . . . . ?
C2 O1 C7 C8 -174.21(15) . . . . ?
C12 C7 C8 C9 -1.6(3) . . . . ?
O1 C7 C8 C9 179.04(15) . . . . ?
C12 C7 C8 C13 175.73(17) . . . . ?
O1 C7 C8 C13 -3.6(2) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C13 C8 C9 C10 -177.13(17) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
O1 C7 C12 C11 -178.75(16) . . . . ?
C8 C7 C12 C11 1.9(3) . . . . ?
C10 C11 C12 C7 -0.8(3) . . . . ?
C9 C8 C13 C16 -124.90(19) . . . . ?
C7 C8 C13 C16 57.9(2) . . . . ?
C9 C8 C13 C15 113.22(19) . . . . ?
C7 C8 C13 C15 -63.9(2) . . . . ?
C9 C8 C13 C14 -5.4(2) . . . . ?
C7 C8 C13 C14 177.41(17) . . . . ?
C18 O2 C17 C3 174.60(16) . . . . ?
C4 C3 C17 O2 -21.9(2) . . . . ?
C2 C3 C17 O2 158.51(16) . . . . ?
O3 S1 C19 C20 160.77(13) . . . . ?
C1 S1 C19 C20 50.45(14) . . . . ?
O3 S1 C19 C22 37.81(16) . . . . ?
C1 S1 C19 C22 -72.52(15) . . . . ?
O3 S1 C19 C21 -80.07(14) . . . . ?
C1 S1 C19 C21 169.61(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.071


# Attachment '4z s2228.cif'

data_s2228
_database_code_depnum_ccdc_archive 'CCDC 623110'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;

_publ_section_exptl_refinement   
;
The structure was solved by the direct methods.
The non H atoms were refined anisotropically.
H atoms were included in calculated positions.
The absolute configuration could not be determined
by refining the Flack parameter because the anomalous
signal was too low.

;

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H29 N3 O2'
_chemical_formula_weight         367.48

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   25.675(3)
_cell_length_b                   39.811(4)
_cell_length_c                   7.9886(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     8165.5(15)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3901
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.29

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3168
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11773
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         26.50
_reflns_number_total             2263
_reflns_number_gt                2012
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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^)+(0.0383P)^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
_chemical_absolute_configuration UKN
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2263
_refine_ls_number_parameters     250
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0672
_refine_ls_wR_factor_gt          0.0656
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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
O1 O 0.28354(5) 0.06300(3) 0.81687(18) 0.0254(3) Uani 1 1 d . . .
O2 O 0.10699(5) 0.08449(3) 0.87944(17) 0.0219(3) Uani 1 1 d . . .
N1 N 0.22313(6) 0.10316(4) 0.7504(2) 0.0190(4) Uani 1 1 d . . .
N2 N 0.25195(5) 0.09583(4) 1.0262(2) 0.0175(3) Uani 1 1 d . . .
N3 N 0.14697(5) 0.04561(4) 1.0429(2) 0.0174(3) Uani 1 1 d . . .
C1 C 0.21875(7) 0.13893(4) 0.7548(2) 0.0174(4) Uani 1 1 d . . .
C2 C 0.17207(7) 0.15376(5) 0.7102(3) 0.0207(4) Uani 1 1 d . . .
H2 H 0.1429 0.1401 0.6838 0.025 Uiso 1 1 calc R . .
C3 C 0.16758(7) 0.18840(5) 0.7036(3) 0.0243(5) Uani 1 1 d . . .
H3 H 0.1355 0.1984 0.6714 0.029 Uiso 1 1 calc R . .
C4 C 0.20973(7) 0.20833(5) 0.7439(3) 0.0262(5) Uani 1 1 d . . .
H4 H 0.2067 0.2321 0.7400 0.031 Uiso 1 1 calc R . .
C5 C 0.25624(7) 0.19368(5) 0.7899(3) 0.0272(5) Uani 1 1 d . . .
H5 H 0.2851 0.2074 0.8188 0.033 Uiso 1 1 calc R . .
C6 C 0.26123(7) 0.15894(5) 0.7943(3) 0.0230(4) Uani 1 1 d . . .
H6 H 0.2935 0.1490 0.8242 0.028 Uiso 1 1 calc R . .
C7 C 0.21495(9) 0.08752(5) 0.5876(3) 0.0326(5) Uani 1 1 d . . .
H7A H 0.2419 0.0952 0.5096 0.049 Uiso 1 1 calc R . .
H7B H 0.1806 0.0938 0.5446 0.049 Uiso 1 1 calc R . .
H7C H 0.2169 0.0630 0.5992 0.049 Uiso 1 1 calc R . .
C8 C 0.25510(7) 0.08591(4) 0.8610(3) 0.0178(4) Uani 1 1 d . . .
C9 C 0.29523(7) 0.08665(5) 1.1373(3) 0.0224(4) Uani 1 1 d . . .
H9A H 0.3121 0.0663 1.0951 0.034 Uiso 1 1 calc R . .
H9B H 0.2818 0.0825 1.2503 0.034 Uiso 1 1 calc R . .
H9C H 0.3206 0.1050 1.1406 0.034 Uiso 1 1 calc R . .
C10 C 0.21168(7) 0.11610(4) 1.0987(2) 0.0170(4) Uani 1 1 d . . .
C11 C 0.22634(7) 0.14495(5) 1.1861(3) 0.0199(4) Uani 1 1 d . . .
H11 H 0.2617 0.1519 1.1853 0.024 Uiso 1 1 calc R . .
C12 C 0.18994(7) 0.16356(5) 1.2738(3) 0.0242(4) Uani 1 1 d . . .
H12 H 0.2005 0.1831 1.3332 0.029 Uiso 1 1 calc R . .
C13 C 0.13811(7) 0.15386(5) 1.2753(3) 0.0236(4) Uani 1 1 d . . .
H13 H 0.1131 0.1664 1.3369 0.028 Uiso 1 1 calc R . .
C14 C 0.12335(7) 0.12569(5) 1.1856(3) 0.0205(4) Uani 1 1 d . . .
H14 H 0.0877 0.1194 1.1842 0.025 Uiso 1 1 calc R . .
C15 C 0.15938(7) 0.10627(5) 1.0972(2) 0.0171(4) Uani 1 1 d . . .
C16 C 0.13676(6) 0.07752(4) 0.9957(2) 0.0174(4) Uani 1 1 d . . .
C17 C 0.17879(7) 0.03698(5) 1.1908(3) 0.0200(4) Uani 1 1 d . . .
H17 H 0.1942 0.0584 1.2340 0.024 Uiso 1 1 calc R . .
C18 C 0.14560(8) 0.02235(5) 1.3293(3) 0.0307(5) Uani 1 1 d . . .
H18A H 0.1195 0.0389 1.3641 0.046 Uiso 1 1 calc R . .
H18B H 0.1678 0.0166 1.4249 0.046 Uiso 1 1 calc R . .
H18C H 0.1280 0.0021 1.2885 0.046 Uiso 1 1 calc R . .
C19 C 0.22392(8) 0.01384(5) 1.1443(3) 0.0282(5) Uani 1 1 d . . .
H19A H 0.2104 -0.0086 1.1183 0.042 Uiso 1 1 calc R . .
H19B H 0.2482 0.0124 1.2385 0.042 Uiso 1 1 calc R . .
H19C H 0.2421 0.0229 1.0462 0.042 Uiso 1 1 calc R . .
C20 C 0.12106(7) 0.01727(5) 0.9555(3) 0.0216(4) Uani 1 1 d . . .
H20 H 0.1339 -0.0038 1.0103 0.026 Uiso 1 1 calc R . .
C21 C 0.06209(7) 0.01756(5) 0.9772(3) 0.0304(5) Uani 1 1 d . . .
H21A H 0.0535 0.0195 1.0963 0.046 Uiso 1 1 calc R . .
H21B H 0.0475 -0.0034 0.9328 0.046 Uiso 1 1 calc R . .
H21C H 0.0473 0.0367 0.9163 0.046 Uiso 1 1 calc R . .
C22 C 0.13690(7) 0.01502(5) 0.7736(3) 0.0290(5) Uani 1 1 d . . .
H22A H 0.1212 0.0336 0.7112 0.043 Uiso 1 1 calc R . .
H22B H 0.1249 -0.0064 0.7268 0.043 Uiso 1 1 calc R . .
H22C H 0.1749 0.0163 0.7649 0.043 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
O1 0.0278(7) 0.0214(7) 0.0270(8) -0.0034(6) 0.0026(7) 0.0064(6)
O2 0.0189(7) 0.0229(7) 0.0241(8) 0.0016(6) -0.0068(6) 0.0018(6)
N1 0.0229(8) 0.0166(8) 0.0173(9) -0.0023(7) 0.0006(7) -0.0011(6)
N2 0.0163(7) 0.0169(8) 0.0192(9) -0.0021(7) 0.0009(7) 0.0005(6)
N3 0.0174(7) 0.0170(8) 0.0178(9) 0.0012(7) -0.0011(7) -0.0005(6)
C1 0.0218(9) 0.0170(9) 0.0135(9) 0.0011(8) 0.0048(8) 0.0000(7)
C2 0.0196(9) 0.0220(10) 0.0206(11) -0.0001(9) 0.0014(8) -0.0032(8)
C3 0.0216(10) 0.0245(11) 0.0270(12) 0.0039(9) 0.0034(9) 0.0040(8)
C4 0.0320(11) 0.0169(10) 0.0295(12) 0.0011(9) 0.0046(9) -0.0011(8)
C5 0.0258(10) 0.0227(11) 0.0331(13) 0.0013(9) 0.0002(10) -0.0083(8)
C6 0.0201(9) 0.0233(10) 0.0255(11) 0.0039(9) 0.0002(8) 0.0002(8)
C7 0.0535(14) 0.0250(11) 0.0192(12) -0.0033(9) -0.0039(10) -0.0012(10)
C8 0.0164(9) 0.0163(9) 0.0208(10) 0.0004(8) 0.0022(8) -0.0041(8)
C9 0.0179(9) 0.0255(10) 0.0237(12) 0.0007(9) -0.0024(8) 0.0001(8)
C10 0.0190(9) 0.0174(9) 0.0145(10) 0.0037(8) 0.0008(8) 0.0026(8)
C11 0.0218(10) 0.0196(10) 0.0184(10) 0.0008(8) -0.0009(8) -0.0027(8)
C12 0.0340(11) 0.0183(10) 0.0203(11) -0.0028(9) 0.0002(9) -0.0019(9)
C13 0.0290(10) 0.0223(10) 0.0196(11) 0.0003(9) 0.0035(9) 0.0079(9)
C14 0.0189(9) 0.0228(10) 0.0197(10) 0.0029(9) -0.0004(8) 0.0018(8)
C15 0.0196(9) 0.0176(9) 0.0141(10) 0.0031(8) -0.0003(8) 0.0009(7)
C16 0.0128(8) 0.0224(10) 0.0172(10) 0.0004(8) 0.0030(8) 0.0008(7)
C17 0.0217(9) 0.0182(10) 0.0202(10) 0.0038(8) -0.0047(8) -0.0019(8)
C18 0.0369(12) 0.0303(12) 0.0248(12) 0.0049(10) -0.0007(10) -0.0049(10)
C19 0.0243(10) 0.0249(11) 0.0354(14) 0.0077(10) -0.0064(9) 0.0018(8)
C20 0.0213(9) 0.0162(10) 0.0273(11) -0.0004(9) -0.0023(8) -0.0025(8)
C21 0.0217(10) 0.0298(12) 0.0397(14) -0.0017(10) 0.0005(10) -0.0081(9)
C22 0.0268(11) 0.0294(12) 0.0307(13) -0.0085(10) -0.0040(10) 0.0008(9)

_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
O1 C8 1.220(2) . ?
O2 C16 1.234(2) . ?
N1 C8 1.388(2) . ?
N1 C1 1.429(2) . ?
N1 C7 1.457(3) . ?
N2 C8 1.380(3) . ?
N2 C10 1.434(2) . ?
N2 C9 1.468(2) . ?
N3 C16 1.351(2) . ?
N3 C17 1.477(2) . ?
N3 C20 1.484(2) . ?
C1 C2 1.383(3) . ?
C1 C6 1.387(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.396(3) . ?
C10 C15 1.399(2) . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.398(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.518(3) . ?
C17 C18 1.513(3) . ?
C17 C19 1.526(3) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C22 1.512(3) . ?
C20 C21 1.524(3) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C8 N1 C1 121.59(15) . . ?
C8 N1 C7 116.24(16) . . ?
C1 N1 C7 115.90(16) . . ?
C8 N2 C10 126.13(15) . . ?
C8 N2 C9 117.56(15) . . ?
C10 N2 C9 116.20(16) . . ?
C16 N3 C17 123.34(15) . . ?
C16 N3 C20 119.76(16) . . ?
C17 N3 C20 116.58(15) . . ?
C2 C1 C6 119.66(17) . . ?
C2 C1 N1 119.17(16) . . ?
C6 C1 N1 121.08(16) . . ?
C1 C2 C3 120.48(17) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 119.90(17) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 119.88(18) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.51(18) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.58(17) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N2 121.69(18) . . ?
O1 C8 N1 122.65(19) . . ?
N2 C8 N1 115.65(16) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 119.55(16) . . ?
C11 C10 N2 118.09(15) . . ?
C15 C10 N2 122.11(15) . . ?
C12 C11 C10 120.79(17) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.27(18) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 118.98(18) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 121.92(17) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C14 C15 C10 118.46(17) . . ?
C14 C15 C16 115.71(15) . . ?
C10 C15 C16 125.64(16) . . ?
O2 C16 N3 122.82(17) . . ?
O2 C16 C15 117.97(16) . . ?
N3 C16 C15 119.04(16) . . ?
N3 C17 C18 111.26(14) . . ?
N3 C17 C19 111.47(17) . . ?
C18 C17 C19 111.92(17) . . ?
N3 C17 H17 107.3 . . ?
C18 C17 H17 107.3 . . ?
C19 C17 H17 107.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 C22 112.13(16) . . ?
N3 C20 C21 112.70(16) . . ?
C22 C20 C21 112.14(18) . . ?
N3 C20 H20 106.4 . . ?
C22 C20 H20 106.4 . . ?
C21 C20 H20 106.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
C8 N1 C1 C2 -148.28(18) . . . . ?
C7 N1 C1 C2 60.6(2) . . . . ?
C8 N1 C1 C6 35.2(3) . . . . ?
C7 N1 C1 C6 -115.9(2) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
N1 C1 C2 C3 -176.12(19) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
N1 C1 C6 C5 177.02(19) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C10 N2 C8 O1 -163.55(16) . . . . ?
C9 N2 C8 O1 20.4(2) . . . . ?
C10 N2 C8 N1 15.2(2) . . . . ?
C9 N2 C8 N1 -160.91(15) . . . . ?
C1 N1 C8 O1 -136.05(18) . . . . ?
C7 N1 C8 O1 15.0(3) . . . . ?
C1 N1 C8 N2 45.3(2) . . . . ?
C7 N1 C8 N2 -163.71(16) . . . . ?
C8 N2 C10 C11 -126.18(19) . . . . ?
C9 N2 C10 C11 49.9(2) . . . . ?
C8 N2 C10 C15 59.7(3) . . . . ?
C9 N2 C10 C15 -124.23(19) . . . . ?
C15 C10 C11 C12 1.2(3) . . . . ?
N2 C10 C11 C12 -173.07(18) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
C12 C13 C14 C15 1.6(3) . . . . ?
C13 C14 C15 C10 -0.8(3) . . . . ?
C13 C14 C15 C16 -176.09(19) . . . . ?
C11 C10 C15 C14 -0.7(3) . . . . ?
N2 C10 C15 C14 173.40(18) . . . . ?
C11 C10 C15 C16 174.14(18) . . . . ?
N2 C10 C15 C16 -11.8(3) . . . . ?
C17 N3 C16 O2 -174.46(16) . . . . ?
C20 N3 C16 O2 -1.2(3) . . . . ?
C17 N3 C16 C15 0.7(2) . . . . ?
C20 N3 C16 C15 174.03(15) . . . . ?
C14 C15 C16 O2 63.3(2) . . . . ?
C10 C15 C16 O2 -111.6(2) . . . . ?
C14 C15 C16 N3 -112.14(19) . . . . ?
C10 C15 C16 N3 72.9(2) . . . . ?
C16 N3 C17 C18 109.32(19) . . . . ?
C20 N3 C17 C18 -64.2(2) . . . . ?
C16 N3 C17 C19 -124.99(19) . . . . ?
C20 N3 C17 C19 61.5(2) . . . . ?
C16 N3 C20 C22 64.4(2) . . . . ?
C17 N3 C20 C22 -121.89(18) . . . . ?
C16 N3 C20 C21 -63.3(2) . . . . ?
C17 N3 C20 C21 110.44(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032

# Attachment '10y s2275 corrected.cif'

data_s2275m
_database_code_depnum_ccdc_archive 'CCDC 623111'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H42 N4 O3'
_chemical_formula_weight         542.71

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'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.5280(5)
_cell_length_b                   15.8200(8)
_cell_length_c                   20.1410(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3035.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9457
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.21

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9627
_exptl_absorpt_correction_T_max  0.9700
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26380
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         28.28
_reflns_number_total             4121
_reflns_number_gt                3648
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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^)+(0.0564P)^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   -0.6(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4121
_refine_ls_number_parameters     369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.004
_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
C1 C 0.51783(19) 0.88957(11) 0.08683(8) 0.0223(4) Uani 1 1 d . . .
C2 C 0.5113(2) 0.81508(12) 0.05020(9) 0.0277(4) Uani 1 1 d . . .
H2 H 0.5924 0.7952 0.0277 0.033 Uiso 1 1 calc R . .
C3 C 0.3873(2) 0.76990(13) 0.04637(9) 0.0321(4) Uani 1 1 d . . .
H3 H 0.3840 0.7182 0.0224 0.039 Uiso 1 1 calc R . .
C4 C 0.2678(2) 0.80041(14) 0.07770(9) 0.0333(5) Uani 1 1 d . . .
H4 H 0.1825 0.7695 0.0753 0.040 Uiso 1 1 calc R . .
C5 C 0.2730(2) 0.87569(14) 0.11226(9) 0.0310(4) Uani 1 1 d . . .
H5 H 0.1906 0.8970 0.1328 0.037 Uiso 1 1 calc R . .
C6 C 0.39733(19) 0.92022(12) 0.11723(9) 0.0261(4) Uani 1 1 d . . .
H6 H 0.4004 0.9717 0.1414 0.031 Uiso 1 1 calc R . .
C7 C 0.6565(2) 1.01995(12) 0.06632(11) 0.0367(5) Uani 1 1 d . . .
H7A H 0.7238 1.0527 0.0926 0.055 Uiso 1 1 calc R . .
H7B H 0.5640 1.0469 0.0686 0.055 Uiso 1 1 calc R . .
H7C H 0.6878 1.0178 0.0200 0.055 Uiso 1 1 calc R . .
C8 C 0.77036(19) 0.89380(12) 0.10923(9) 0.0242(4) Uani 1 1 d . . .
C9 C 0.8648(2) 0.76013(12) 0.14815(10) 0.0309(4) Uani 1 1 d . . .
H9A H 0.8458 0.7225 0.1106 0.046 Uiso 1 1 calc R . .
H9B H 0.8649 0.7273 0.1894 0.046 Uiso 1 1 calc R . .
H9C H 0.9566 0.7870 0.1421 0.046 Uiso 1 1 calc R . .
C10 C 0.64647(17) 0.81565(10) 0.19902(8) 0.0179(3) Uani 1 1 d . . .
C11 C 0.56249(18) 0.74393(10) 0.19811(8) 0.0206(3) Uani 1 1 d . . .
H11 H 0.5772 0.7021 0.1650 0.025 Uiso 1 1 calc R . .
C12 C 0.45735(18) 0.73257(11) 0.24489(9) 0.0218(3) Uani 1 1 d . . .
H12 H 0.4017 0.6828 0.2443 0.026 Uiso 1 1 calc R . .
C13 C 0.43389(17) 0.79412(11) 0.29250(8) 0.0201(3) Uani 1 1 d . . .
H13 H 0.3593 0.7876 0.3234 0.024 Uiso 1 1 calc R . .
C14 C 0.51916(17) 0.86545(10) 0.29528(8) 0.0172(3) Uani 1 1 d . . .
C15 C 0.62691(17) 0.87610(10) 0.24898(8) 0.0166(3) Uani 1 1 d . . .
C16 C 0.71683(17) 0.95460(10) 0.25343(8) 0.0171(3) Uani 1 1 d . . .
C17 C 0.92463(18) 1.02580(11) 0.29787(9) 0.0225(4) Uani 1 1 d . . .
H17 H 1.0120 1.0074 0.3213 0.027 Uiso 1 1 calc R . .
C18 C 0.9713(2) 1.06651(13) 0.23319(10) 0.0312(4) Uani 1 1 d . . .
H18A H 1.0165 1.0240 0.2050 0.047 Uiso 1 1 calc R . .
H18B H 1.0380 1.1121 0.2427 0.047 Uiso 1 1 calc R . .
H18C H 0.8894 1.0898 0.2101 0.047 Uiso 1 1 calc R . .
C19 C 0.8499(2) 1.08735(11) 0.34438(10) 0.0287(4) Uani 1 1 d . . .
H19A H 0.7653 1.1091 0.3226 0.043 Uiso 1 1 calc R . .
H19B H 0.9128 1.1345 0.3550 0.043 Uiso 1 1 calc R . .
H19C H 0.8236 1.0580 0.3854 0.043 Uiso 1 1 calc R . .
C20 C 0.89153(18) 0.86875(11) 0.31639(9) 0.0216(4) Uani 1 1 d . . .
H20 H 0.8275 0.8224 0.3015 0.026 Uiso 1 1 calc R . .
C21 C 0.8848(2) 0.87219(13) 0.39220(9) 0.0289(4) Uani 1 1 d . . .
H21A H 0.9455 0.9177 0.4084 0.043 Uiso 1 1 calc R . .
H21B H 0.9166 0.8181 0.4106 0.043 Uiso 1 1 calc R . .
H21C H 0.7879 0.8829 0.4062 0.043 Uiso 1 1 calc R . .
C22 C 1.0390(2) 0.84662(12) 0.29266(11) 0.0322(4) Uani 1 1 d . . .
H22A H 1.0445 0.8538 0.2444 0.048 Uiso 1 1 calc R . .
H22B H 1.0602 0.7878 0.3042 0.048 Uiso 1 1 calc R . .
H22C H 1.1072 0.8841 0.3142 0.048 Uiso 1 1 calc R . .
C23 C 0.49789(16) 0.92941(10) 0.34998(8) 0.0179(3) Uani 1 1 d . . .
H23 H 0.5689 0.9756 0.3456 0.021 Uiso 1 1 calc R . .
C24 C 0.35983(18) 1.00952(10) 0.41603(8) 0.0199(3) Uani 1 1 d . . .
H24 H 0.4193 1.0613 0.4117 0.024 Uiso 1 1 calc R . .
C25 C 0.43887(18) 0.94432(11) 0.46019(8) 0.0203(3) Uani 1 1 d . . .
H25 H 0.5095 0.9747 0.4881 0.024 Uiso 1 1 calc R . .
C26 C 0.33180(19) 1.02067(11) 0.29486(8) 0.0223(4) Uani 1 1 d . . .
H26A H 0.4109 1.0596 0.2894 0.033 Uiso 1 1 calc R . .
H26B H 0.2455 1.0531 0.3023 0.033 Uiso 1 1 calc R . .
H26C H 0.3216 0.9863 0.2547 0.033 Uiso 1 1 calc R . .
C27 C 0.2154(2) 1.03572(12) 0.44003(9) 0.0249(4) Uani 1 1 d . . .
H27A H 0.1742 1.0757 0.4084 0.037 Uiso 1 1 calc R . .
H27B H 0.2235 1.0627 0.4837 0.037 Uiso 1 1 calc R . .
H27C H 0.1552 0.9857 0.4435 0.037 Uiso 1 1 calc R . .
C28 C 0.34687(18) 0.89134(11) 0.50438(8) 0.0209(3) Uani 1 1 d . . .
C29 C 0.2577(2) 0.82981(12) 0.47810(9) 0.0276(4) Uani 1 1 d . . .
H29 H 0.2595 0.8181 0.4319 0.033 Uiso 1 1 calc R . .
C30 C 0.1667(2) 0.78584(12) 0.51894(10) 0.0318(4) Uani 1 1 d . . .
H30 H 0.1062 0.7441 0.5008 0.038 Uiso 1 1 calc R . .
C31 C 0.1640(2) 0.80274(13) 0.58639(10) 0.0330(4) Uani 1 1 d . . .
H31 H 0.1005 0.7731 0.6144 0.040 Uiso 1 1 calc R . .
C32 C 0.2527(2) 0.86216(13) 0.61294(10) 0.0339(5) Uani 1 1 d . . .
H32 H 0.2513 0.8730 0.6593 0.041 Uiso 1 1 calc R . .
C33 C 0.3447(2) 0.90650(11) 0.57220(9) 0.0259(4) Uani 1 1 d . . .
H33 H 0.4063 0.9473 0.5909 0.031 Uiso 1 1 calc R . .
N1 N 0.64739(16) 0.93394(10) 0.09290(7) 0.0246(3) Uani 1 1 d . . .
N2 N 0.75649(15) 0.82491(9) 0.15158(7) 0.0219(3) Uani 1 1 d . . .
N3 N 0.84045(15) 0.94839(8) 0.28631(7) 0.0185(3) Uani 1 1 d . . .
N4 N 0.35756(14) 0.96567(8) 0.35173(7) 0.0176(3) Uani 1 1 d . . .
O1 O 0.88493(14) 0.91620(9) 0.08832(7) 0.0351(3) Uani 1 1 d . . .
O2 O 0.67221(13) 1.02129(7) 0.23024(6) 0.0223(3) Uani 1 1 d . . .
O3 O 0.51143(12) 0.89048(8) 0.41327(6) 0.0210(3) Uani 1 1 d . . .

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
C1 0.0257(9) 0.0245(9) 0.0168(8) 0.0056(7) -0.0022(7) 0.0025(7)
C2 0.0317(10) 0.0327(10) 0.0187(8) -0.0006(7) -0.0007(7) 0.0045(8)
C3 0.0426(11) 0.0322(10) 0.0216(9) -0.0004(8) -0.0084(8) -0.0041(9)
C4 0.0302(10) 0.0459(12) 0.0240(9) 0.0084(9) -0.0056(8) -0.0084(9)
C5 0.0269(9) 0.0445(12) 0.0217(8) 0.0076(9) 0.0021(8) 0.0029(9)
C6 0.0314(9) 0.0288(9) 0.0181(8) 0.0036(7) 0.0000(7) 0.0053(8)
C7 0.0414(12) 0.0295(10) 0.0393(11) 0.0128(9) -0.0003(10) -0.0011(9)
C8 0.0267(9) 0.0252(9) 0.0208(8) -0.0027(7) 0.0026(7) -0.0006(7)
C9 0.0296(10) 0.0305(10) 0.0326(10) -0.0036(8) 0.0047(8) 0.0115(8)
C10 0.0173(8) 0.0191(8) 0.0174(8) 0.0014(6) -0.0034(6) 0.0039(6)
C11 0.0261(8) 0.0166(8) 0.0191(8) -0.0021(6) -0.0047(7) 0.0028(7)
C12 0.0232(8) 0.0175(8) 0.0246(8) 0.0013(7) -0.0066(7) -0.0038(7)
C13 0.0181(8) 0.0223(8) 0.0198(8) 0.0026(7) -0.0007(7) -0.0007(7)
C14 0.0166(7) 0.0175(7) 0.0176(8) 0.0011(6) -0.0038(6) 0.0011(6)
C15 0.0159(7) 0.0169(7) 0.0170(7) 0.0015(6) -0.0042(6) 0.0007(6)
C16 0.0178(7) 0.0197(8) 0.0139(7) -0.0013(6) 0.0027(6) -0.0005(6)
C17 0.0201(8) 0.0222(9) 0.0251(9) 0.0006(7) -0.0032(7) -0.0048(7)
C18 0.0304(10) 0.0310(10) 0.0323(10) 0.0057(8) -0.0005(8) -0.0116(8)
C19 0.0274(9) 0.0254(9) 0.0335(10) -0.0055(8) -0.0046(8) -0.0029(8)
C20 0.0188(8) 0.0184(8) 0.0277(9) 0.0029(7) -0.0049(7) -0.0015(7)
C21 0.0245(9) 0.0335(10) 0.0286(10) 0.0092(8) -0.0077(8) -0.0054(8)
C22 0.0240(9) 0.0275(10) 0.0451(12) -0.0013(9) -0.0002(9) 0.0043(8)
C23 0.0174(8) 0.0191(8) 0.0172(7) 0.0005(7) -0.0008(6) -0.0027(6)
C24 0.0231(8) 0.0186(8) 0.0179(8) -0.0018(6) -0.0003(7) -0.0033(7)
C25 0.0188(8) 0.0252(9) 0.0168(8) -0.0029(7) -0.0011(7) -0.0021(7)
C26 0.0247(8) 0.0209(8) 0.0213(8) 0.0012(7) -0.0001(7) 0.0020(7)
C27 0.0276(9) 0.0261(9) 0.0210(8) -0.0029(7) 0.0006(7) 0.0050(8)
C28 0.0184(8) 0.0229(8) 0.0212(8) 0.0025(7) -0.0005(7) 0.0025(7)
C29 0.0287(10) 0.0301(9) 0.0239(9) 0.0031(8) -0.0023(8) -0.0050(8)
C30 0.0292(10) 0.0286(10) 0.0375(10) 0.0078(8) -0.0012(8) -0.0043(8)
C31 0.0319(10) 0.0310(10) 0.0360(10) 0.0133(9) 0.0113(9) 0.0046(9)
C32 0.0451(12) 0.0354(11) 0.0213(9) 0.0046(8) 0.0085(9) 0.0091(9)
C33 0.0304(9) 0.0258(9) 0.0216(8) 0.0003(7) 0.0004(7) 0.0036(8)
N1 0.0265(8) 0.0241(7) 0.0233(8) 0.0040(6) 0.0000(6) 0.0016(6)
N2 0.0205(7) 0.0232(7) 0.0219(7) -0.0003(6) 0.0017(6) 0.0057(6)
N3 0.0173(6) 0.0170(6) 0.0210(7) 0.0012(5) -0.0016(6) -0.0026(5)
N4 0.0183(7) 0.0182(6) 0.0164(6) -0.0003(6) 0.0009(6) -0.0004(5)
O1 0.0272(7) 0.0404(8) 0.0376(8) 0.0050(7) 0.0112(6) -0.0015(6)
O2 0.0228(6) 0.0200(6) 0.0242(6) 0.0033(5) -0.0022(5) 0.0004(5)
O3 0.0209(6) 0.0267(6) 0.0155(5) 0.0009(5) 0.0000(5) 0.0029(5)

_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
C1 C6 1.388(2) . ?
C1 C2 1.392(3) . ?
C1 N1 1.425(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.465(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O1 1.222(2) . ?
C8 N1 1.373(2) . ?
C8 N2 1.390(2) . ?
C9 N2 1.456(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.388(2) . ?
C10 C15 1.401(2) . ?
C10 N2 1.426(2) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(2) . ?
C14 C23 1.510(2) . ?
C15 C16 1.511(2) . ?
C16 O2 1.230(2) . ?
C16 N3 1.355(2) . ?
C17 N3 1.482(2) . ?
C17 C18 1.520(3) . ?
C17 C19 1.527(3) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N3 1.480(2) . ?
C20 C22 1.525(3) . ?
C20 C21 1.529(2) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 O3 1.4215(19) . ?
C23 N4 1.455(2) . ?
C23 H23 1.0000 . ?
C24 N4 1.469(2) . ?
C24 C27 1.516(2) . ?
C24 C25 1.556(2) . ?
C24 H24 1.0000 . ?
C25 O3 1.448(2) . ?
C25 C28 1.504(2) . ?
C25 H25 1.0000 . ?
C26 N4 1.459(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C33 1.387(2) . ?
C28 C29 1.396(2) . ?
C29 C30 1.383(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.385(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.373(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.391(3) . ?
C32 H32 0.9500 . ?
C33 H33 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
C6 C1 C2 119.50(17) . . ?
C6 C1 N1 120.42(16) . . ?
C2 C1 N1 120.08(16) . . ?
C3 C2 C1 120.36(18) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.71(18) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.96(19) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.49(19) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.92(18) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N1 123.07(17) . . ?
O1 C8 N2 121.56(17) . . ?
N1 C8 N2 115.37(15) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 119.39(15) . . ?
C11 C10 N2 119.92(15) . . ?
C15 C10 N2 120.60(15) . . ?
C12 C11 C10 120.88(15) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 119.72(15) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.26(15) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.00(15) . . ?
C13 C14 C23 119.64(14) . . ?
C15 C14 C23 120.33(14) . . ?
C14 C15 C10 119.67(15) . . ?
C14 C15 C16 118.43(14) . . ?
C10 C15 C16 121.88(14) . . ?
O2 C16 N3 123.26(15) . . ?
O2 C16 C15 119.11(14) . . ?
N3 C16 C15 117.53(14) . . ?
N3 C17 C18 111.95(15) . . ?
N3 C17 C19 111.76(14) . . ?
C18 C17 C19 113.07(16) . . ?
N3 C17 H17 106.5 . . ?
C18 C17 H17 106.5 . . ?
C19 C17 H17 106.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 C22 111.72(15) . . ?
N3 C20 C21 111.38(15) . . ?
C22 C20 C21 111.09(16) . . ?
N3 C20 H20 107.5 . . ?
C22 C20 H20 107.5 . . ?
C21 C20 H20 107.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 N4 103.44(12) . . ?
O3 C23 C14 110.60(13) . . ?
N4 C23 C14 113.90(13) . . ?
O3 C23 H23 109.6 . . ?
N4 C23 H23 109.6 . . ?
C14 C23 H23 109.6 . . ?
N4 C24 C27 113.37(14) . . ?
N4 C24 C25 101.42(13) . . ?
C27 C24 C25 115.98(14) . . ?
N4 C24 H24 108.6 . . ?
C27 C24 H24 108.6 . . ?
C25 C24 H24 108.6 . . ?
O3 C25 C28 109.66(14) . . ?
O3 C25 C24 104.35(12) . . ?
C28 C25 C24 115.18(14) . . ?
O3 C25 H25 109.1 . . ?
C28 C25 H25 109.1 . . ?
C24 C25 H25 109.1 . . ?
N4 C26 H26A 109.5 . . ?
N4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C33 C28 C29 119.00(17) . . ?
C33 C28 C25 119.66(16) . . ?
C29 C28 C25 121.26(15) . . ?
C30 C29 C28 120.46(18) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 119.88(19) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C32 C31 C30 120.18(18) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C33 120.26(18) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C28 C33 C32 120.21(18) . . ?
C28 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C8 N1 C1 122.14(14) . . ?
C8 N1 C7 117.82(16) . . ?
C1 N1 C7 118.53(16) . . ?
C8 N2 C10 124.17(14) . . ?
C8 N2 C9 117.08(15) . . ?
C10 N2 C9 118.72(14) . . ?
C16 N3 C20 123.20(14) . . ?
C16 N3 C17 119.16(13) . . ?
C20 N3 C17 117.45(13) . . ?
C23 N4 C26 111.75(13) . . ?
C23 N4 C24 101.18(13) . . ?
C26 N4 C24 114.38(13) . . ?
C23 O3 C25 106.68(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -2.8(3) . . . . ?
N1 C1 C2 C3 177.34(16) . . . . ?
C1 C2 C3 C4 1.9(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
N1 C1 C6 C5 -178.54(16) . . . . ?
C15 C10 C11 C12 1.7(2) . . . . ?
N2 C10 C11 C12 178.25(15) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C11 C12 C13 C14 -2.7(2) . . . . ?
C12 C13 C14 C15 1.5(2) . . . . ?
C12 C13 C14 C23 -176.31(15) . . . . ?
C13 C14 C15 C10 1.4(2) . . . . ?
C23 C14 C15 C10 179.18(14) . . . . ?
C13 C14 C15 C16 179.71(14) . . . . ?
C23 C14 C15 C16 -2.5(2) . . . . ?
C11 C10 C15 C14 -3.0(2) . . . . ?
N2 C10 C15 C14 -179.50(14) . . . . ?
C11 C10 C15 C16 178.78(15) . . . . ?
N2 C10 C15 C16 2.3(2) . . . . ?
C14 C15 C16 O2 -80.4(2) . . . . ?
C10 C15 C16 O2 97.90(19) . . . . ?
C14 C15 C16 N3 96.17(18) . . . . ?
C10 C15 C16 N3 -85.58(19) . . . . ?
C13 C14 C23 O3 57.57(19) . . . . ?
C15 C14 C23 O3 -120.19(15) . . . . ?
C13 C14 C23 N4 -58.4(2) . . . . ?
C15 C14 C23 N4 123.81(16) . . . . ?
N4 C24 C25 O3 19.52(16) . . . . ?
C27 C24 C25 O3 142.79(14) . . . . ?
N4 C24 C25 C28 -100.75(16) . . . . ?
C27 C24 C25 C28 22.5(2) . . . . ?
O3 C25 C28 C33 135.64(16) . . . . ?
C24 C25 C28 C33 -107.05(18) . . . . ?
O3 C25 C28 C29 -47.7(2) . . . . ?
C24 C25 C28 C29 69.6(2) . . . . ?
C33 C28 C29 C30 1.2(3) . . . . ?
C25 C28 C29 C30 -175.42(17) . . . . ?
C28 C29 C30 C31 -0.1(3) . . . . ?
C29 C30 C31 C32 -0.9(3) . . . . ?
C30 C31 C32 C33 0.8(3) . . . . ?
C29 C28 C33 C32 -1.4(3) . . . . ?
C25 C28 C33 C32 175.34(17) . . . . ?
C31 C32 C33 C28 0.4(3) . . . . ?
O1 C8 N1 C1 147.18(18) . . . . ?
N2 C8 N1 C1 -32.7(2) . . . . ?
O1 C8 N1 C7 -18.6(3) . . . . ?
N2 C8 N1 C7 161.56(16) . . . . ?
C6 C1 N1 C8 132.40(18) . . . . ?
C2 C1 N1 C8 -47.7(2) . . . . ?
C6 C1 N1 C7 -62.0(2) . . . . ?
C2 C1 N1 C7 117.93(19) . . . . ?
O1 C8 N2 C10 152.10(18) . . . . ?
N1 C8 N2 C10 -28.0(2) . . . . ?
O1 C8 N2 C9 -25.7(3) . . . . ?
N1 C8 N2 C9 154.17(16) . . . . ?
C11 C10 N2 C8 124.58(18) . . . . ?
C15 C10 N2 C8 -58.9(2) . . . . ?
C11 C10 N2 C9 -57.6(2) . . . . ?
C15 C10 N2 C9 118.86(17) . . . . ?
O2 C16 N3 C20 177.63(16) . . . . ?
C15 C16 N3 C20 1.3(2) . . . . ?
O2 C16 N3 C17 2.7(2) . . . . ?
C15 C16 N3 C17 -173.67(14) . . . . ?
C22 C20 N3 C16 126.45(17) . . . . ?
C21 C20 N3 C16 -108.67(17) . . . . ?
C22 C20 N3 C17 -58.54(19) . . . . ?
C21 C20 N3 C17 66.35(19) . . . . ?
C18 C17 N3 C16 -62.2(2) . . . . ?
C19 C17 N3 C16 65.8(2) . . . . ?
C18 C17 N3 C20 122.57(17) . . . . ?
C19 C17 N3 C20 -109.42(17) . . . . ?
O3 C23 N4 C26 170.64(12) . . . . ?
C14 C23 N4 C26 -69.25(17) . . . . ?
O3 C23 N4 C24 48.51(14) . . . . ?
C14 C23 N4 C24 168.62(13) . . . . ?
C27 C24 N4 C23 -165.62(14) . . . . ?
C25 C24 N4 C23 -40.58(15) . . . . ?
C27 C24 N4 C26 74.10(18) . . . . ?
C25 C24 N4 C26 -160.87(14) . . . . ?
N4 C23 O3 C25 -36.07(15) . . . . ?
C14 C23 O3 C25 -158.41(13) . . . . ?
C28 C25 O3 C23 133.63(14) . . . . ?
C24 C25 O3 C23 9.73(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037