# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_akwe206

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H34 Cl2 F12 N2 O3 Si'
_chemical_formula_sum            'C37 H34 Cl2 F12 N2 O3 Si'
_chemical_formula_weight         881.65
_chemical_absolute_configuration unk

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   C2221

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

_cell_length_a                   10.8393(5)
_cell_length_b                   16.7856(3)
_cell_length_c                   42.689(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7767.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13497
_cell_measurement_theta_min      1.91
_cell_measurement_theta_max      24.99
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3600
_exptl_absorpt_coefficient_mu    0.295
_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  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/Omega-Scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13497
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_sigmaI/netI    0.1473
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         24.99
_reflns_number_total             6177
_reflns_number_gt                3443
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius COLLECT'
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2004)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0811P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    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   -0.13(12)
_refine_ls_number_reflns         6177
_refine_ls_number_parameters     518
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1651
_refine_ls_wR_factor_gt          0.1412
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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
Cl1 Cl 0.2489(2) 0.39547(10) -0.01348(5) 0.0503(6) Uani 1 1 d . . .
Cl2 Cl -0.0893(2) 0.4080(2) -0.10460(5) 0.0988(11) Uani 1 1 d . . .
Si1 Si 0.05260(16) 0.47359(11) 0.18298(4) 0.0280(5) Uani 1 1 d . . .
F1 F 0.5732(4) 0.3112(3) 0.17825(12) 0.0780(17) Uani 1 1 d . . .
F2 F 0.4984(7) 0.2034(4) 0.17081(17) 0.137(3) Uani 1 1 d . . .
F3 F 0.4266(4) 0.2727(6) 0.20635(12) 0.159(4) Uani 1 1 d . . .
F4 F 0.3246(6) 0.4161(4) 0.05679(14) 0.125(3) Uani 1 1 d . . .
F5 F 0.4876(6) 0.4147(5) 0.07325(17) 0.142(3) Uani 1 1 d . . .
F6 F 0.3745(10) 0.5038(3) 0.08549(16) 0.217(6) Uani 1 1 d . . .
F7 F -0.3221(4) 0.1761(3) 0.23602(10) 0.0584(13) Uani 1 1 d . . .
F8 F -0.1780(4) 0.2184(3) 0.26614(9) 0.0528(13) Uani 1 1 d . . .
F9 F -0.2778(3) 0.2996(2) 0.23717(9) 0.0421(11) Uani 1 1 d . . .
F10 F 0.1144(7) 0.0334(3) 0.15545(15) 0.119(3) Uani 1 1 d . . .
F11 F -0.0411(4) -0.0134(3) 0.17941(17) 0.097(2) Uani 1 1 d . . .
F12 F 0.1132(5) 0.0199(3) 0.20361(15) 0.096(2) Uani 1 1 d . . .
O1 O 0.0443(5) 0.4034(3) 0.04592(11) 0.0470(14) Uani 1 1 d . . .
O2 O -0.1506(5) 0.3725(3) 0.04125(13) 0.0564(17) Uani 1 1 d . . .
O3 O -0.0125(4) 0.4059(2) 0.15960(9) 0.0256(11) Uani 1 1 d . . .
N1 N -0.0427(7) 0.3554(3) 0.04249(13) 0.0389(15) Uani 1 1 d . . .
N2 N -0.0374(4) 0.2479(3) 0.10000(11) 0.0247(13) Uani 1 1 d . . .
C1 C 0.1143(6) 0.3561(4) -0.02956(17) 0.038(2) Uani 1 1 d . . .
C2 C 0.0733(8) 0.3921(5) -0.05672(18) 0.049(2) Uani 1 1 d . . .
H2 H 0.1170 0.4358 -0.0655 0.058 Uiso 1 1 calc R . .
C3 C -0.0318(8) 0.3637(6) -0.07089(18) 0.058(3) Uani 1 1 d . . .
C4 C -0.0943(7) 0.2970(6) -0.05851(18) 0.054(2) Uani 1 1 d . . .
H4 H -0.1639 0.2752 -0.0690 0.064 Uiso 1 1 calc R . .
C5 C -0.0523(6) 0.2641(5) -0.03095(16) 0.041(2) Uani 1 1 d . . .
H5 H -0.0958 0.2206 -0.0220 0.049 Uiso 1 1 calc R . .
C6 C 0.0544(6) 0.2937(4) -0.01551(15) 0.0308(17) Uani 1 1 d . . .
C7 C 0.0918(6) 0.2555(4) 0.01535(15) 0.0305(17) Uani 1 1 d . . .
H7 H 0.1701 0.2813 0.0225 0.037 Uiso 1 1 calc R . .
C8 C -0.0065(5) 0.2682(4) 0.04102(14) 0.0239(16) Uani 1 1 d . . .
H8 H -0.0811 0.2356 0.0359 0.029 Uiso 1 1 calc R . .
C9 C 0.0448(6) 0.2422(4) 0.07330(14) 0.0246(15) Uani 1 1 d . . .
H9 H 0.1173 0.2772 0.0779 0.030 Uiso 1 1 calc R . .
C10 C -0.0560(6) 0.3240(4) 0.11580(14) 0.0239(16) Uani 1 1 d . . .
H10 H -0.0332 0.3685 0.1013 0.029 Uiso 1 1 calc R . .
C11 C 0.0234(5) 0.3298(3) 0.14663(14) 0.0214(16) Uani 1 1 d . . .
C12 C -0.0809(6) 0.5302(4) 0.19736(16) 0.0372(19) Uani 1 1 d . . .
H12A H -0.1226 0.5558 0.1797 0.056 Uiso 1 1 calc R . .
H12B H -0.0529 0.5709 0.2122 0.056 Uiso 1 1 calc R . .
H12C H -0.1383 0.4939 0.2079 0.056 Uiso 1 1 calc R . .
C13 C 0.1599(6) 0.5384(4) 0.16119(16) 0.0364(19) Uani 1 1 d . . .
H13A H 0.2326 0.5075 0.1549 0.055 Uiso 1 1 calc R . .
H13B H 0.1856 0.5828 0.1746 0.055 Uiso 1 1 calc R . .
H13C H 0.1186 0.5592 0.1425 0.055 Uiso 1 1 calc R . .
C14 C 0.1360(7) 0.4289(4) 0.21682(16) 0.040(2) Uani 1 1 d . . .
H14A H 0.0868 0.3853 0.2256 0.060 Uiso 1 1 calc R . .
H14B H 0.1494 0.4696 0.2329 0.060 Uiso 1 1 calc R . .
H14C H 0.2158 0.4081 0.2098 0.060 Uiso 1 1 calc R . .
C15 C 0.1643(6) 0.3336(4) 0.14010(15) 0.0229(16) Uani 1 1 d . . .
C16 C 0.2505(6) 0.3006(4) 0.16044(15) 0.0265(16) Uani 1 1 d . . .
H16 H 0.2222 0.2714 0.1781 0.032 Uiso 1 1 calc R . .
C17 C 0.3757(6) 0.3089(4) 0.15580(15) 0.0251(16) Uani 1 1 d . . .
C18 C 0.4656(8) 0.2743(5) 0.1789(2) 0.048(2) Uani 1 1 d . . .
C19 C 0.4190(6) 0.3516(4) 0.13004(15) 0.0285(17) Uani 1 1 d . . .
H19 H 0.5052 0.3576 0.1266 0.034 Uiso 1 1 calc R . .
C20 C 0.3351(6) 0.3853(4) 0.10951(15) 0.0271(17) Uani 1 1 d . . .
C21 C 0.3805(7) 0.4342(6) 0.08370(19) 0.046(2) Uani 1 1 d . . .
C22 C 0.2075(6) 0.3788(4) 0.11477(16) 0.0275(17) Uani 1 1 d . . .
H22 H 0.1508 0.4048 0.1012 0.033 Uiso 1 1 calc R . .
C23 C -0.0119(6) 0.2636(4) 0.16883(15) 0.0232(16) Uani 1 1 d . . .
C24 C -0.0948(5) 0.2762(4) 0.19303(15) 0.0234(16) Uani 1 1 d . . .
H24 H -0.1243 0.3287 0.1967 0.028 Uiso 1 1 calc R . .
C25 C -0.1372(6) 0.2136(4) 0.21259(15) 0.0266(17) Uani 1 1 d . . .
C26 C -0.2272(7) 0.2269(5) 0.23735(15) 0.0364(19) Uani 1 1 d . . .
C27 C -0.0929(6) 0.1380(4) 0.20735(16) 0.0329(18) Uani 1 1 d . . .
H27 H -0.1210 0.0950 0.2200 0.040 Uiso 1 1 calc R . .
C28 C -0.0070(6) 0.1240(4) 0.18362(18) 0.0316(18) Uani 1 1 d . . .
C29 C 0.0410(7) 0.0425(4) 0.17956(19) 0.0391(19) Uani 1 1 d . . .
C30 C 0.0317(6) 0.1872(4) 0.16419(15) 0.0256(16) Uani 1 1 d . . .
H30 H 0.0885 0.1772 0.1477 0.031 Uiso 1 1 calc R . .
C31 C -0.1970(5) 0.3274(4) 0.12285(15) 0.0293(18) Uani 1 1 d . . .
H31A H -0.2122 0.3490 0.1441 0.035 Uiso 1 1 calc R . .
H31B H -0.2399 0.3615 0.1074 0.035 Uiso 1 1 calc R . .
C32 C -0.2413(7) 0.2422(4) 0.12051(19) 0.050(2) Uani 1 1 d . . .
H32A H -0.2336 0.2147 0.1409 0.060 Uiso 1 1 calc R . .
H32B H -0.3284 0.2401 0.1136 0.060 Uiso 1 1 calc R . .
C33 C -0.1575(6) 0.2052(4) 0.09644(15) 0.0356(19) Uani 1 1 d . . .
H33A H -0.1473 0.1475 0.1004 0.043 Uiso 1 1 calc R . .
H33B H -0.1911 0.2127 0.0751 0.043 Uiso 1 1 calc R . .
C34 C 0.0940(5) 0.1577(4) 0.06959(15) 0.0238(16) Uani 1 1 d . . .
H34 H 0.1013 0.1268 0.0881 0.029 Uiso 1 1 calc R . .
C35 C 0.1276(6) 0.1230(4) 0.04296(17) 0.0277(17) Uani 1 1 d . . .
C36 C 0.1157(6) 0.1654(4) 0.01199(16) 0.0320(17) Uani 1 1 d . . .
H36A H 0.0471 0.1412 0.0000 0.038 Uiso 1 1 calc R . .
H36B H 0.1925 0.1573 -0.0002 0.038 Uiso 1 1 calc R . .
C37 C 0.1802(6) 0.0417(4) 0.04209(16) 0.0312(17) Uani 1 1 d . . .
H37A H 0.1977 0.0238 0.0635 0.047 Uiso 1 1 calc R . .
H37B H 0.2567 0.0421 0.0299 0.047 Uiso 1 1 calc R . .
H37C H 0.1208 0.0053 0.0323 0.047 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.743(7) . ?
Cl2 C3 1.735(8) . ?
Si1 O3 1.669(4) . ?
Si1 C12 1.836(7) . ?
Si1 C13 1.844(7) . ?
Si1 C14 1.862(7) . ?
F1 C18 1.321(8) . ?
F2 C18 1.288(9) . ?
F3 C18 1.247(9) . ?
F4 C21 1.334(9) . ?
F5 C21 1.285(9) . ?
F6 C21 1.173(10) . ?
F7 C26 1.337(7) . ?
F8 C26 1.347(7) . ?
F9 C26 1.337(8) . ?
F10 C29 1.309(9) . ?
F11 C29 1.294(8) . ?
F12 C29 1.346(8) . ?
O1 N1 1.248(7) . ?
O2 N1 1.205(7) . ?
O3 C11 1.445(7) . ?
N1 C8 1.517(8) . ?
N2 C9 1.450(7) . ?
N2 C10 1.460(8) . ?
N2 C33 1.492(8) . ?
C1 C6 1.371(9) . ?
C1 C2 1.381(10) . ?
C2 C3 1.375(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.412(11) . ?
C4 C5 1.377(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.421(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.520(9) . ?
C7 C36 1.542(8) . ?
C7 C8 1.544(8) . ?
C7 H7 1.0000 . ?
C8 C9 1.549(8) . ?
C8 H8 1.0000 . ?
C9 C34 1.524(8) . ?
C9 H9 1.0000 . ?
C10 C31 1.558(8) . ?
C10 C11 1.576(8) . ?
C10 H10 1.0000 . ?
C11 C23 1.511(8) . ?
C11 C15 1.553(8) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.391(8) . ?
C15 C22 1.401(9) . ?
C16 C17 1.378(8) . ?
C16 H16 0.9500 . ?
C17 C19 1.395(9) . ?
C17 C18 1.502(9) . ?
C19 C20 1.384(8) . ?
C19 H19 0.9500 . ?
C20 C22 1.406(9) . ?
C20 C21 1.460(9) . ?
C22 H22 0.9500 . ?
C23 C30 1.380(8) . ?
C23 C24 1.385(8) . ?
C24 C25 1.419(9) . ?
C24 H24 0.9500 . ?
C25 C27 1.376(9) . ?
C25 C26 1.456(9) . ?
C27 C28 1.396(9) . ?
C27 H27 0.9500 . ?
C28 C30 1.411(9) . ?
C28 C29 1.473(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.512(9) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.506(9) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.328(8) . ?
C34 H34 0.9500 . ?
C35 C37 1.480(8) . ?
C35 C36 1.507(9) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 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 Si1 C12 102.7(3) . . ?
O3 Si1 C13 111.5(3) . . ?
C12 Si1 C13 111.1(3) . . ?
O3 Si1 C14 113.2(3) . . ?
C12 Si1 C14 109.4(3) . . ?
C13 Si1 C14 108.8(3) . . ?
C11 O3 Si1 135.8(4) . . ?
O2 N1 O1 125.8(6) . . ?
O2 N1 C8 118.6(7) . . ?
O1 N1 C8 115.6(6) . . ?
C9 N2 C10 120.3(5) . . ?
C9 N2 C33 115.1(5) . . ?
C10 N2 C33 110.3(5) . . ?
C6 C1 C2 123.3(7) . . ?
C6 C1 Cl1 120.9(6) . . ?
C2 C1 Cl1 115.8(6) . . ?
C3 C2 C1 119.0(8) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.5(8) . . ?
C2 C3 Cl2 120.9(8) . . ?
C4 C3 Cl2 118.6(7) . . ?
C5 C4 C3 118.6(8) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 121.7(8) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 116.7(7) . . ?
C1 C6 C7 125.1(7) . . ?
C5 C6 C7 118.2(6) . . ?
C6 C7 C36 112.2(5) . . ?
C6 C7 C8 111.9(5) . . ?
C36 C7 C8 108.5(5) . . ?
C6 C7 H7 108.0 . . ?
C36 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
N1 C8 C7 109.9(5) . . ?
N1 C8 C9 109.1(5) . . ?
C7 C8 C9 110.2(5) . . ?
N1 C8 H8 109.2 . . ?
C7 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
N2 C9 C34 110.9(5) . . ?
N2 C9 C8 117.4(5) . . ?
C34 C9 C8 107.2(5) . . ?
N2 C9 H9 106.9 . . ?
C34 C9 H9 106.9 . . ?
C8 C9 H9 106.9 . . ?
N2 C10 C31 104.9(5) . . ?
N2 C10 C11 111.4(5) . . ?
C31 C10 C11 111.9(5) . . ?
N2 C10 H10 109.5 . . ?
C31 C10 H10 109.5 . . ?
C11 C10 H10 109.5 . . ?
O3 C11 C23 110.0(5) . . ?
O3 C11 C15 107.3(4) . . ?
C23 C11 C15 113.1(5) . . ?
O3 C11 C10 103.1(5) . . ?
C23 C11 C10 109.9(5) . . ?
C15 C11 C10 112.9(5) . . ?
Si1 C12 H12A 109.5 . . ?
Si1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si1 C14 H14A 109.5 . . ?
Si1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C22 118.2(6) . . ?
C16 C15 C11 122.2(6) . . ?
C22 C15 C11 119.3(6) . . ?
C17 C16 C15 122.2(6) . . ?
C17 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C16 C17 C19 119.7(6) . . ?
C16 C17 C18 120.4(6) . . ?
C19 C17 C18 119.9(6) . . ?
F3 C18 F2 109.0(8) . . ?
F3 C18 F1 109.2(7) . . ?
F2 C18 F1 100.5(8) . . ?
F3 C18 C17 114.0(7) . . ?
F2 C18 C17 111.1(7) . . ?
F1 C18 C17 112.2(7) . . ?
C20 C19 C17 119.2(6) . . ?
C20 C19 H19 120.4 . . ?
C17 C19 H19 120.4 . . ?
C19 C20 C22 120.9(6) . . ?
C19 C20 C21 119.1(6) . . ?
C22 C20 C21 119.8(6) . . ?
F6 C21 F5 109.0(8) . . ?
F6 C21 F4 104.9(8) . . ?
F5 C21 F4 93.1(8) . . ?
F6 C21 C20 119.5(9) . . ?
F5 C21 C20 115.0(7) . . ?
F4 C21 C20 111.6(6) . . ?
C15 C22 C20 119.6(6) . . ?
C15 C22 H22 120.2 . . ?
C20 C22 H22 120.2 . . ?
C30 C23 C24 118.1(6) . . ?
C30 C23 C11 120.4(6) . . ?
C24 C23 C11 121.3(6) . . ?
C23 C24 C25 122.4(6) . . ?
C23 C24 H24 118.8 . . ?
C25 C24 H24 118.8 . . ?
C27 C25 C24 118.3(6) . . ?
C27 C25 C26 119.6(6) . . ?
C24 C25 C26 122.1(6) . . ?
F7 C26 F9 105.5(6) . . ?
F7 C26 F8 106.0(5) . . ?
F9 C26 F8 105.3(5) . . ?
F7 C26 C25 112.7(6) . . ?
F9 C26 C25 114.2(6) . . ?
F8 C26 C25 112.4(6) . . ?
C25 C27 C28 120.4(6) . . ?
C25 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C30 119.9(6) . . ?
C27 C28 C29 118.5(7) . . ?
C30 C28 C29 121.6(7) . . ?
F11 C29 F10 109.2(7) . . ?
F11 C29 F12 101.5(6) . . ?
F10 C29 F12 102.3(7) . . ?
F11 C29 C28 115.5(6) . . ?
F10 C29 C28 114.5(7) . . ?
F12 C29 C28 112.2(6) . . ?
C23 C30 C28 120.8(6) . . ?
C23 C30 H30 119.6 . . ?
C28 C30 H30 119.6 . . ?
C32 C31 C10 105.3(5) . . ?
C32 C31 H31A 110.7 . . ?
C10 C31 H31A 110.7 . . ?
C32 C31 H31B 110.7 . . ?
C10 C31 H31B 110.7 . . ?
H31A C31 H31B 108.8 . . ?
C33 C32 C31 104.1(6) . . ?
C33 C32 H32A 110.9 . . ?
C31 C32 H32A 110.9 . . ?
C33 C32 H32B 110.9 . . ?
C31 C32 H32B 110.9 . . ?
H32A C32 H32B 109.0 . . ?
N2 C33 C32 105.0(5) . . ?
N2 C33 H33A 110.7 . . ?
C32 C33 H33A 110.7 . . ?
N2 C33 H33B 110.7 . . ?
C32 C33 H33B 110.7 . . ?
H33A C33 H33B 108.8 . . ?
C35 C34 C9 126.4(6) . . ?
C35 C34 H34 116.8 . . ?
C9 C34 H34 116.8 . . ?
C34 C35 C37 122.1(6) . . ?
C34 C35 C36 121.4(6) . . ?
C37 C35 C36 116.5(6) . . ?
C35 C36 C7 113.3(5) . . ?
C35 C36 H36A 108.9 . . ?
C7 C36 H36A 108.9 . . ?
C35 C36 H36B 108.9 . . ?
C7 C36 H36B 108.9 . . ?
H36A C36 H36B 107.7 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 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
C12 Si1 O3 C11 -160.3(5) . . . . ?
C13 Si1 O3 C11 80.7(6) . . . . ?
C14 Si1 O3 C11 -42.5(6) . . . . ?
C6 C1 C2 C3 -1.0(11) . . . . ?
Cl1 C1 C2 C3 179.4(6) . . . . ?
C1 C2 C3 C4 -2.3(11) . . . . ?
C1 C2 C3 Cl2 178.6(5) . . . . ?
C2 C3 C4 C5 4.0(11) . . . . ?
Cl2 C3 C4 C5 -176.9(5) . . . . ?
C3 C4 C5 C6 -2.5(10) . . . . ?
C2 C1 C6 C5 2.4(10) . . . . ?
Cl1 C1 C6 C5 -178.0(5) . . . . ?
C2 C1 C6 C7 -176.2(6) . . . . ?
Cl1 C1 C6 C7 3.4(9) . . . . ?
C4 C5 C6 C1 -0.6(10) . . . . ?
C4 C5 C6 C7 178.1(6) . . . . ?
C1 C6 C7 C36 -123.0(7) . . . . ?
C5 C6 C7 C36 58.4(8) . . . . ?
C1 C6 C7 C8 114.8(7) . . . . ?
C5 C6 C7 C8 -63.8(8) . . . . ?
O2 N1 C8 C7 128.0(6) . . . . ?
O1 N1 C8 C7 -54.1(7) . . . . ?
O2 N1 C8 C9 -111.0(6) . . . . ?
O1 N1 C8 C9 66.8(7) . . . . ?
C6 C7 C8 N1 -49.5(7) . . . . ?
C36 C7 C8 N1 -173.8(5) . . . . ?
C6 C7 C8 C9 -169.8(5) . . . . ?
C36 C7 C8 C9 65.9(7) . . . . ?
C10 N2 C9 C34 155.1(5) . . . . ?
C33 N2 C9 C34 -69.0(7) . . . . ?
C10 N2 C9 C8 -81.2(7) . . . . ?
C33 N2 C9 C8 54.7(8) . . . . ?
N1 C8 C9 N2 61.1(7) . . . . ?
C7 C8 C9 N2 -178.1(5) . . . . ?
N1 C8 C9 C34 -173.3(5) . . . . ?
C7 C8 C9 C34 -52.5(6) . . . . ?
C9 N2 C10 C31 138.7(5) . . . . ?
C33 N2 C10 C31 1.0(6) . . . . ?
C9 N2 C10 C11 -100.1(6) . . . . ?
C33 N2 C10 C11 122.2(5) . . . . ?
Si1 O3 C11 C23 89.0(6) . . . . ?
Si1 O3 C11 C15 -34.4(7) . . . . ?
Si1 O3 C11 C10 -153.9(4) . . . . ?
N2 C10 C11 O3 -176.8(5) . . . . ?
C31 C10 C11 O3 -59.8(6) . . . . ?
N2 C10 C11 C23 -59.6(6) . . . . ?
C31 C10 C11 C23 57.4(7) . . . . ?
N2 C10 C11 C15 67.8(6) . . . . ?
C31 C10 C11 C15 -175.3(5) . . . . ?
O3 C11 C15 C16 99.7(6) . . . . ?
C23 C11 C15 C16 -21.8(8) . . . . ?
C10 C11 C15 C16 -147.4(6) . . . . ?
O3 C11 C15 C22 -73.4(7) . . . . ?
C23 C11 C15 C22 165.1(6) . . . . ?
C10 C11 C15 C22 39.5(8) . . . . ?
C22 C15 C16 C17 -2.1(9) . . . . ?
C11 C15 C16 C17 -175.3(6) . . . . ?
C15 C16 C17 C19 0.1(9) . . . . ?
C15 C16 C17 C18 178.2(6) . . . . ?
C16 C17 C18 F3 -31.0(11) . . . . ?
C19 C17 C18 F3 147.0(8) . . . . ?
C16 C17 C18 F2 92.6(9) . . . . ?
C19 C17 C18 F2 -89.4(9) . . . . ?
C16 C17 C18 F1 -155.8(7) . . . . ?
C19 C17 C18 F1 22.3(10) . . . . ?
C16 C17 C19 C20 0.1(9) . . . . ?
C18 C17 C19 C20 -177.9(6) . . . . ?
C17 C19 C20 C22 1.7(10) . . . . ?
C17 C19 C20 C21 176.2(7) . . . . ?
C19 C20 C21 F6 -102.4(11) . . . . ?
C22 C20 C21 F6 72.1(11) . . . . ?
C19 C20 C21 F5 30.3(11) . . . . ?
C22 C20 C21 F5 -155.2(8) . . . . ?
C19 C20 C21 F4 134.7(7) . . . . ?
C22 C20 C21 F4 -50.8(11) . . . . ?
C16 C15 C22 C20 3.9(9) . . . . ?
C11 C15 C22 C20 177.3(6) . . . . ?
C19 C20 C22 C15 -3.8(10) . . . . ?
C21 C20 C22 C15 -178.2(7) . . . . ?
O3 C11 C23 C30 -168.7(5) . . . . ?
C15 C11 C23 C30 -48.7(8) . . . . ?
C10 C11 C23 C30 78.5(7) . . . . ?
O3 C11 C23 C24 15.6(7) . . . . ?
C15 C11 C23 C24 135.5(6) . . . . ?
C10 C11 C23 C24 -97.2(6) . . . . ?
C30 C23 C24 C25 -1.1(9) . . . . ?
C11 C23 C24 C25 174.7(6) . . . . ?
C23 C24 C25 C27 0.7(9) . . . . ?
C23 C24 C25 C26 -178.0(6) . . . . ?
C27 C25 C26 F7 -49.7(9) . . . . ?
C24 C25 C26 F7 129.0(7) . . . . ?
C27 C25 C26 F9 -170.1(6) . . . . ?
C24 C25 C26 F9 8.6(9) . . . . ?
C27 C25 C26 F8 69.9(8) . . . . ?
C24 C25 C26 F8 -111.3(8) . . . . ?
C24 C25 C27 C28 1.0(9) . . . . ?
C26 C25 C27 C28 179.7(6) . . . . ?
C25 C27 C28 C30 -2.1(10) . . . . ?
C25 C27 C28 C29 178.0(6) . . . . ?
C27 C28 C29 F11 47.2(10) . . . . ?
C30 C28 C29 F11 -132.8(8) . . . . ?
C27 C28 C29 F10 175.4(7) . . . . ?
C30 C28 C29 F10 -4.5(10) . . . . ?
C27 C28 C29 F12 -68.5(9) . . . . ?
C30 C28 C29 F12 111.6(8) . . . . ?
C24 C23 C30 C28 -0.1(9) . . . . ?
C11 C23 C30 C28 -176.0(6) . . . . ?
C27 C28 C30 C23 1.7(10) . . . . ?
C29 C28 C30 C23 -178.4(6) . . . . ?
N2 C10 C31 C32 18.7(7) . . . . ?
C11 C10 C31 C32 -102.2(6) . . . . ?
C10 C31 C32 C33 -30.9(7) . . . . ?
C9 N2 C33 C32 -160.5(6) . . . . ?
C10 N2 C33 C32 -20.3(7) . . . . ?
C31 C32 C33 N2 31.4(7) . . . . ?
N2 C9 C34 C35 151.1(6) . . . . ?
C8 C9 C34 C35 21.7(9) . . . . ?
C9 C34 C35 C37 176.9(6) . . . . ?
C9 C34 C35 C36 -2.2(10) . . . . ?
C34 C35 C36 C7 13.6(9) . . . . ?
C37 C35 C36 C7 -165.6(6) . . . . ?
C6 C7 C36 C35 -168.3(6) . . . . ?
C8 C7 C36 C35 -44.2(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.943
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.943
_refine_diff_density_max         0.815
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.076
_database_code_depnum_ccdc_archive 'CCDC 973119'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_akwe359

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H30 Cl2 N2 O3'
_chemical_formula_sum            'C30 H30 Cl2 N2 O3'
_chemical_formula_weight         537.46

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'
Cl Cl 0.1484 0.1585 '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   P212121

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                   8.9169(13)
_cell_length_b                   17.351(3)
_cell_length_c                   17.602(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2723.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12769
_cell_measurement_theta_min      1.65
_cell_measurement_theta_max      27.00
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    0.273
_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  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/Omega-Scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12769
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_sigmaI/netI    0.1243
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         27.00
_reflns_number_total             5633
_reflns_number_gt                2904
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius COLLECT'
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2004)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0608P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_number_reflns         5633
_refine_ls_number_parameters     339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1520
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1519
_refine_ls_wR_factor_gt          0.1281
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.99621(14) 0.14900(6) 0.36280(7) 0.0562(3) Uani 1 1 d . . .
Cl2 Cl 0.50949(14) 0.04397(7) 0.52176(7) 0.0611(4) Uani 1 1 d . . .
O1 O 0.3620(4) 0.12542(18) 0.3303(2) 0.0635(10) Uani 1 1 d . . .
O2 O 0.5810(4) 0.17783(18) 0.3176(2) 0.0652(10) Uani 1 1 d . . .
O3 O 0.5086(4) -0.01019(18) 0.0528(2) 0.0529(8) Uani 1 1 d . . .
H3 H 0.574(6) -0.034(3) 0.082(3) 0.072(19) Uiso 1 1 d . . .
N1 N 0.4979(5) 0.1226(2) 0.3286(2) 0.0490(10) Uani 1 1 d . . .
N2 N 0.5986(4) 0.03740(19) 0.1925(2) 0.0470(10) Uani 1 1 d . . .
C1 C 0.8703(5) 0.1508(2) 0.4395(3) 0.0465(12) Uani 1 1 d . . .
C2 C 0.7493(5) 0.0998(2) 0.4413(3) 0.0408(11) Uani 1 1 d . . .
C3 C 0.6655(5) 0.1050(2) 0.5079(3) 0.0469(12) Uani 1 1 d . . .
C4 C 0.6949(5) 0.1549(2) 0.5664(3) 0.0480(12) Uani 1 1 d . . .
H4 H 0.6341 0.1548 0.6108 0.058 Uiso 1 1 calc R . .
C5 C 0.8127(6) 0.2048(2) 0.5602(3) 0.0503(13) Uani 1 1 d . . .
H5 H 0.8321 0.2410 0.5995 0.060 Uiso 1 1 calc R . .
C6 C 0.9028(5) 0.2026(2) 0.4973(3) 0.0493(13) Uani 1 1 d . . .
H6 H 0.9866 0.2362 0.4932 0.059 Uiso 1 1 calc R . .
C7 C 0.7192(5) 0.0441(2) 0.3767(3) 0.0426(11) Uani 1 1 d . . .
H7 H 0.7896 0.0590 0.3350 0.051 Uiso 1 1 calc R . .
C8 C 0.5647(5) 0.0430(2) 0.3416(3) 0.0499(13) Uani 1 1 d . . .
H8 H 0.4969 0.0151 0.3776 0.060 Uiso 1 1 calc R . .
C9 C 0.5603(5) -0.0017(2) 0.2638(3) 0.0432(12) Uani 1 1 d . . .
H9 H 0.4530 -0.0173 0.2575 0.052 Uiso 1 1 calc R . .
C10 C 0.4826(5) 0.0835(2) 0.1527(3) 0.0496(12) Uani 1 1 d . . .
H10 H 0.4102 0.1059 0.1900 0.059 Uiso 1 1 calc R . .
C11 C 0.3993(5) 0.0298(2) 0.0954(3) 0.0439(12) Uani 1 1 d . . .
C12 C 0.3033(5) 0.0738(3) 0.0391(3) 0.0481(12) Uani 1 1 d . . .
C13 C 0.2105(6) 0.1344(3) 0.0609(3) 0.0663(16) Uani 1 1 d . . .
H13 H 0.2089 0.1501 0.1126 0.080 Uiso 1 1 calc R . .
C14 C 0.1198(6) 0.1724(3) 0.0082(3) 0.0669(16) Uani 1 1 d . . .
H14 H 0.0550 0.2126 0.0246 0.080 Uiso 1 1 calc R . .
C15 C 0.1238(7) 0.1520(3) -0.0672(3) 0.0681(16) Uani 1 1 d . . .
H15 H 0.0644 0.1790 -0.1032 0.082 Uiso 1 1 calc R . .
C16 C 0.2145(6) 0.0922(3) -0.0901(3) 0.0607(15) Uani 1 1 d . . .
H16 H 0.2154 0.0773 -0.1421 0.073 Uiso 1 1 calc R . .
C17 C 0.3057(6) 0.0527(3) -0.0380(3) 0.0576(14) Uani 1 1 d . . .
H17 H 0.3687 0.0119 -0.0547 0.069 Uiso 1 1 calc R . .
C18 C 0.3002(5) -0.0290(2) 0.1374(3) 0.0397(11) Uani 1 1 d . . .
C19 C 0.3140(5) -0.1077(2) 0.1248(3) 0.0482(13) Uani 1 1 d . . .
H19 H 0.3862 -0.1257 0.0893 0.058 Uiso 1 1 calc R . .
C20 C 0.2252(6) -0.1602(3) 0.1628(3) 0.0593(15) Uani 1 1 d . . .
H20 H 0.2388 -0.2137 0.1536 0.071 Uiso 1 1 calc R . .
C21 C 0.1177(5) -0.1369(3) 0.2136(3) 0.0537(13) Uani 1 1 d . . .
H21 H 0.0558 -0.1734 0.2388 0.064 Uiso 1 1 calc R . .
C22 C 0.1017(5) -0.0590(3) 0.2272(3) 0.0544(13) Uani 1 1 d . . .
H22 H 0.0295 -0.0418 0.2631 0.065 Uiso 1 1 calc R . .
C23 C 0.1891(5) -0.0056(2) 0.1894(3) 0.0454(12) Uani 1 1 d . . .
H23 H 0.1741 0.0478 0.1986 0.054 Uiso 1 1 calc R . .
C24 C 0.5730(6) 0.1480(3) 0.1133(3) 0.0673(15) Uani 1 1 d . . .
H24A H 0.5377 0.1558 0.0605 0.081 Uiso 1 1 calc R . .
H24B H 0.5629 0.1972 0.1413 0.081 Uiso 1 1 calc R . .
C25 C 0.7322(6) 0.1209(3) 0.1141(3) 0.0691(16) Uani 1 1 d . . .
H25A H 0.8022 0.1652 0.1140 0.083 Uiso 1 1 calc R . .
H25B H 0.7534 0.0883 0.0692 0.083 Uiso 1 1 calc R . .
C26 C 0.7477(6) 0.0749(3) 0.1864(3) 0.0638(15) Uani 1 1 d . . .
H26A H 0.8290 0.0363 0.1823 0.077 Uiso 1 1 calc R . .
H26B H 0.7675 0.1088 0.2305 0.077 Uiso 1 1 calc R . .
C27 C 0.6430(5) -0.0760(2) 0.2734(3) 0.0436(12) Uani 1 1 d . . .
H27 H 0.6336 -0.1131 0.2339 0.052 Uiso 1 1 calc R . .
C28 C 0.7295(5) -0.0949(2) 0.3329(3) 0.0461(12) Uani 1 1 d . . .
C29 C 0.7573(5) -0.0400(2) 0.3967(3) 0.0479(12) Uani 1 1 d . . .
H29A H 0.8642 -0.0430 0.4116 0.058 Uiso 1 1 calc R . .
H29B H 0.6965 -0.0559 0.4411 0.058 Uiso 1 1 calc R . .
C30 C 0.7939(5) -0.1742(2) 0.3427(3) 0.0586(14) Uani 1 1 d . . .
H30A H 0.7754 -0.2046 0.2967 0.088 Uiso 1 1 calc R . .
H30B H 0.7461 -0.1994 0.3863 0.088 Uiso 1 1 calc R . .
H30C H 0.9021 -0.1704 0.3516 0.088 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.756(5) . ?
Cl2 C3 1.765(5) . ?
O1 N1 1.213(5) . ?
O2 N1 1.227(5) . ?
O3 C11 1.412(5) . ?
O3 H3 0.88(5) . ?
N1 C8 1.522(5) . ?
N2 C9 1.468(5) . ?
N2 C10 1.483(5) . ?
N2 C26 1.484(6) . ?
C1 C6 1.388(6) . ?
C1 C2 1.396(6) . ?
C2 C3 1.394(6) . ?
C2 C7 1.516(6) . ?
C3 C4 1.371(6) . ?
C4 C5 1.366(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.369(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.511(6) . ?
C7 C29 1.538(5) . ?
C7 H7 1.0000 . ?
C8 C9 1.575(6) . ?
C8 H8 1.0000 . ?
C9 C27 1.495(6) . ?
C9 H9 1.0000 . ?
C10 C24 1.545(7) . ?
C10 C11 1.560(6) . ?
C10 H10 1.0000 . ?
C11 C12 1.515(6) . ?
C11 C18 1.540(6) . ?
C12 C13 1.392(6) . ?
C12 C17 1.406(6) . ?
C13 C14 1.397(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.405(7) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.388(5) . ?
C18 C23 1.408(6) . ?
C19 C20 1.380(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.372(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.380(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(6) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.496(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.509(7) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.341(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.495(6) . ?
C28 C30 1.500(6) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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
C11 O3 H3 112(4) . . ?
O1 N1 O2 125.2(4) . . ?
O1 N1 C8 115.1(4) . . ?
O2 N1 C8 119.7(4) . . ?
C9 N2 C10 119.4(4) . . ?
C9 N2 C26 118.2(4) . . ?
C10 N2 C26 110.8(3) . . ?
C6 C1 C2 123.8(4) . . ?
C6 C1 Cl1 116.2(4) . . ?
C2 C1 Cl1 120.0(4) . . ?
C3 C2 C1 113.1(4) . . ?
C3 C2 C7 125.3(4) . . ?
C1 C2 C7 121.6(4) . . ?
C4 C3 C2 124.8(4) . . ?
C4 C3 Cl2 115.2(4) . . ?
C2 C3 Cl2 120.0(4) . . ?
C5 C4 C3 119.2(4) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 119.9(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.2(4) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C8 C7 C2 118.4(4) . . ?
C8 C7 C29 106.4(3) . . ?
C2 C7 C29 113.2(4) . . ?
C8 C7 H7 106.0 . . ?
C2 C7 H7 106.0 . . ?
C29 C7 H7 106.0 . . ?
C7 C8 N1 114.0(4) . . ?
C7 C8 C9 112.6(4) . . ?
N1 C8 C9 107.9(4) . . ?
C7 C8 H8 107.3 . . ?
N1 C8 H8 107.3 . . ?
C9 C8 H8 107.3 . . ?
N2 C9 C27 112.4(4) . . ?
N2 C9 C8 120.7(3) . . ?
C27 C9 C8 108.3(4) . . ?
N2 C9 H9 104.6 . . ?
C27 C9 H9 104.6 . . ?
C8 C9 H9 104.6 . . ?
N2 C10 C24 103.8(4) . . ?
N2 C10 C11 108.4(3) . . ?
C24 C10 C11 113.0(4) . . ?
N2 C10 H10 110.5 . . ?
C24 C10 H10 110.5 . . ?
C11 C10 H10 110.5 . . ?
O3 C11 C12 106.9(4) . . ?
O3 C11 C18 109.0(3) . . ?
C12 C11 C18 108.9(4) . . ?
O3 C11 C10 107.9(3) . . ?
C12 C11 C10 113.0(3) . . ?
C18 C11 C10 111.1(4) . . ?
C13 C12 C17 118.1(5) . . ?
C13 C12 C11 122.4(4) . . ?
C17 C12 C11 119.5(5) . . ?
C12 C13 C14 121.2(5) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 120.3(5) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.6(5) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 121.1(5) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C12 119.7(5) . . ?
C16 C17 H17 120.2 . . ?
C12 C17 H17 120.2 . . ?
C19 C18 C23 116.7(4) . . ?
C19 C18 C11 121.7(4) . . ?
C23 C18 C11 121.6(4) . . ?
C20 C19 C18 121.4(4) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C21 C20 C19 121.4(4) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 118.3(5) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
C21 C22 C23 121.0(5) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C18 121.1(4) . . ?
C22 C23 H23 119.4 . . ?
C18 C23 H23 119.4 . . ?
C25 C24 C10 105.2(4) . . ?
C25 C24 H24A 110.7 . . ?
C10 C24 H24A 110.7 . . ?
C25 C24 H24B 110.7 . . ?
C10 C24 H24B 110.7 . . ?
H24A C24 H24B 108.8 . . ?
C24 C25 C26 105.1(4) . . ?
C24 C25 H25A 110.7 . . ?
C26 C25 H25A 110.7 . . ?
C24 C25 H25B 110.7 . . ?
C26 C25 H25B 110.7 . . ?
H25A C25 H25B 108.8 . . ?
N2 C26 C25 102.2(4) . . ?
N2 C26 H26A 111.3 . . ?
C25 C26 H26A 111.3 . . ?
N2 C26 H26B 111.3 . . ?
C25 C26 H26B 111.3 . . ?
H26A C26 H26B 109.2 . . ?
C28 C27 C9 125.7(4) . . ?
C28 C27 H27 117.2 . . ?
C9 C27 H27 117.2 . . ?
C27 C28 C29 121.7(4) . . ?
C27 C28 C30 122.3(4) . . ?
C29 C28 C30 115.8(4) . . ?
C28 C29 C7 113.4(4) . . ?
C28 C29 H29A 108.9 . . ?
C7 C29 H29A 108.9 . . ?
C28 C29 H29B 108.9 . . ?
C7 C29 H29B 108.9 . . ?
H29A C29 H29B 107.7 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
C6 C1 C2 C3 -1.3(6) . . . . ?
Cl1 C1 C2 C3 176.1(3) . . . . ?
C6 C1 C2 C7 -179.7(4) . . . . ?
Cl1 C1 C2 C7 -2.4(5) . . . . ?
C1 C2 C3 C4 0.7(6) . . . . ?
C7 C2 C3 C4 179.0(4) . . . . ?
C1 C2 C3 Cl2 -178.9(3) . . . . ?
C7 C2 C3 Cl2 -0.5(6) . . . . ?
C2 C3 C4 C5 1.1(7) . . . . ?
Cl2 C3 C4 C5 -179.3(3) . . . . ?
C3 C4 C5 C6 -2.4(7) . . . . ?
C4 C5 C6 C1 1.8(7) . . . . ?
C2 C1 C6 C5 0.1(7) . . . . ?
Cl1 C1 C6 C5 -177.3(3) . . . . ?
C3 C2 C7 C8 54.3(6) . . . . ?
C1 C2 C7 C8 -127.4(4) . . . . ?
C3 C2 C7 C29 -71.3(5) . . . . ?
C1 C2 C7 C29 107.0(5) . . . . ?
C2 C7 C8 N1 42.6(6) . . . . ?
C29 C7 C8 N1 171.5(4) . . . . ?
C2 C7 C8 C9 166.0(4) . . . . ?
C29 C7 C8 C9 -65.2(5) . . . . ?
O1 N1 C8 C7 -151.6(4) . . . . ?
O2 N1 C8 C7 28.2(6) . . . . ?
O1 N1 C8 C9 82.5(5) . . . . ?
O2 N1 C8 C9 -97.7(4) . . . . ?
C10 N2 C9 C27 147.0(4) . . . . ?
C26 N2 C9 C27 -73.1(5) . . . . ?
C10 N2 C9 C8 -83.3(5) . . . . ?
C26 N2 C9 C8 56.6(5) . . . . ?
C7 C8 C9 N2 -85.3(5) . . . . ?
N1 C8 C9 N2 41.4(5) . . . . ?
C7 C8 C9 C27 46.2(5) . . . . ?
N1 C8 C9 C27 172.9(4) . . . . ?
C9 N2 C10 C24 148.9(4) . . . . ?
C26 N2 C10 C24 6.2(5) . . . . ?
C9 N2 C10 C11 -90.7(4) . . . . ?
C26 N2 C10 C11 126.7(4) . . . . ?
N2 C10 C11 O3 -49.0(5) . . . . ?
C24 C10 C11 O3 65.5(4) . . . . ?
N2 C10 C11 C12 -166.9(4) . . . . ?
C24 C10 C11 C12 -52.4(5) . . . . ?
N2 C10 C11 C18 70.4(5) . . . . ?
C24 C10 C11 C18 -175.1(4) . . . . ?
O3 C11 C12 C13 -163.0(4) . . . . ?
C18 C11 C12 C13 79.5(5) . . . . ?
C10 C11 C12 C13 -44.4(6) . . . . ?
O3 C11 C12 C17 17.7(5) . . . . ?
C18 C11 C12 C17 -99.8(5) . . . . ?
C10 C11 C12 C17 136.3(4) . . . . ?
C17 C12 C13 C14 1.2(7) . . . . ?
C11 C12 C13 C14 -178.1(4) . . . . ?
C12 C13 C14 C15 -1.9(8) . . . . ?
C13 C14 C15 C16 2.0(8) . . . . ?
C14 C15 C16 C17 -1.4(7) . . . . ?
C15 C16 C17 C12 0.8(7) . . . . ?
C13 C12 C17 C16 -0.7(7) . . . . ?
C11 C12 C17 C16 178.6(4) . . . . ?
O3 C11 C18 C19 -6.5(6) . . . . ?
C12 C11 C18 C19 109.7(5) . . . . ?
C10 C11 C18 C19 -125.3(4) . . . . ?
O3 C11 C18 C23 174.7(4) . . . . ?
C12 C11 C18 C23 -69.1(5) . . . . ?
C10 C11 C18 C23 55.9(5) . . . . ?
C23 C18 C19 C20 -1.4(7) . . . . ?
C11 C18 C19 C20 179.8(4) . . . . ?
C18 C19 C20 C21 1.1(7) . . . . ?
C19 C20 C21 C22 -1.2(7) . . . . ?
C20 C21 C22 C23 1.5(7) . . . . ?
C21 C22 C23 C18 -1.8(7) . . . . ?
C19 C18 C23 C22 1.7(6) . . . . ?
C11 C18 C23 C22 -179.4(4) . . . . ?
N2 C10 C24 C25 16.4(5) . . . . ?
C11 C10 C24 C25 -100.8(5) . . . . ?
C10 C24 C25 C26 -32.8(5) . . . . ?
C9 N2 C26 C25 -169.0(4) . . . . ?
C10 N2 C26 C25 -25.9(5) . . . . ?
C24 C25 C26 N2 35.7(5) . . . . ?
N2 C9 C27 C28 124.5(5) . . . . ?
C8 C9 C27 C28 -11.4(6) . . . . ?
C9 C27 C28 C29 -2.5(7) . . . . ?
C9 C27 C28 C30 172.5(4) . . . . ?
C27 C28 C29 C7 -17.1(6) . . . . ?
C30 C28 C29 C7 167.7(4) . . . . ?
C8 C7 C29 C28 48.9(5) . . . . ?
C2 C7 C29 C28 -179.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 973120'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_akwe296_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 N2 O3'
_chemical_formula_sum            'C15 H18 N2 O3'
_chemical_formula_weight         274.31

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           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   19.3984(10)
_cell_length_b                   9.6352(5)
_cell_length_c                   16.2688(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.737(2)
_cell_angle_gamma                90.00
_cell_volume                     2879.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13657
_cell_measurement_theta_min      1.11
_cell_measurement_theta_max      27.00
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .06
_exptl_crystal_size_min          .02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.089
_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  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/Omega-Scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13657
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_sigmaI/netI    0.1054
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.11
_diffrn_reflns_theta_max         27.00
_reflns_number_total             5758
_reflns_number_gt                2893
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius COLLECT'
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2004)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0774P)²+1.3869P] where P=(Fo²+2Fc²)/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         5758
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1482
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1851
_refine_ls_wR_factor_gt          0.1537
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_refine_ls_shift/su_max          0.007
_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
O1 O 0.14977(13) -0.6794(3) 0.44394(15) 0.0489(7) Uani 1 1 d . . .
O2 O 0.12064(15) -0.8779(3) 0.38183(16) 0.0563(7) Uani 1 1 d . . .
O3 O 0.29159(13) -0.8910(2) 0.32886(18) 0.0538(7) Uani 1 1 d . . .
N1 N 0.12768(14) -0.7522(3) 0.37941(17) 0.0348(7) Uani 1 1 d . . .
N2 N 0.24585(13) -0.6751(3) 0.32430(16) 0.0317(6) Uani 1 1 d . . .
H2A H 0.2535 -0.5910 0.3362 0.038 Uiso 1 1 d R . .
C1 C 0.11007(16) -0.6868(3) 0.2904(2) 0.0330(8) Uani 1 1 d . . .
H1 H 0.0678 -0.7379 0.2501 0.040 Uiso 1 1 calc R . .
C2 C 0.17595(16) -0.7092(3) 0.2591(2) 0.0332(8) Uani 1 1 d . . .
H2 H 0.1772 -0.8098 0.2446 0.040 Uiso 1 1 calc R . .
C3 C 0.29959(17) -0.7689(3) 0.3530(2) 0.0342(8) Uani 1 1 d . . .
C4 C 0.36954(17) -0.7176(4) 0.4152(2) 0.0430(9) Uani 1 1 d . . .
H4A H 0.3765 -0.7576 0.4726 0.064 Uiso 1 1 calc R . .
H4B H 0.3681 -0.6162 0.4187 0.064 Uiso 1 1 calc R . .
H4C H 0.4099 -0.7453 0.3949 0.064 Uiso 1 1 calc R . .
C5 C 0.16566(18) -0.6280(3) 0.1772(2) 0.0361(8) Uani 1 1 d . . .
H5 H 0.1953 -0.6519 0.1428 0.043 Uiso 1 1 calc R . .
C6 C 0.11835(18) -0.5254(4) 0.1493(2) 0.0356(8) Uani 1 1 d . . .
C7 C 0.06798(19) -0.4824(4) 0.1972(2) 0.0385(9) Uani 1 1 d . . .
H7A H 0.0184 -0.5157 0.1648 0.046 Uiso 1 1 calc R . .
H7B H 0.0663 -0.3797 0.1983 0.046 Uiso 1 1 calc R . .
C8 C 0.08853(18) -0.5361(3) 0.2914(2) 0.0347(8) Uani 1 1 d . . .
H8 H 0.1319 -0.4830 0.3277 0.042 Uiso 1 1 calc R . .
C9 C 0.02674(17) -0.5116(3) 0.3273(2) 0.0322(8) Uani 1 1 d . . .
C10 C -0.03889(17) -0.5811(4) 0.2959(2) 0.0375(8) Uani 1 1 d . . .
H10 H -0.0448 -0.6490 0.2518 0.045 Uiso 1 1 calc R . .
C11 C -0.09627(19) -0.5548(4) 0.3268(2) 0.0436(9) Uani 1 1 d . . .
H11 H -0.1405 -0.6050 0.3045 0.052 Uiso 1 1 calc R . .
C12 C -0.08885(19) -0.4553(4) 0.3902(2) 0.0419(9) Uani 1 1 d . . .
H12 H -0.1280 -0.4367 0.4117 0.050 Uiso 1 1 calc R . .
C13 C -0.0246(2) -0.3834(4) 0.4221(2) 0.0437(9) Uani 1 1 d . . .
H13 H -0.0194 -0.3145 0.4655 0.052 Uiso 1 1 calc R . .
C14 C 0.03282(18) -0.4116(4) 0.3910(2) 0.0370(8) Uani 1 1 d . . .
H14 H 0.0771 -0.3616 0.4136 0.044 Uiso 1 1 calc R . .
C15 C 0.11072(19) -0.4469(4) 0.0666(2) 0.0455(10) Uani 1 1 d . . .
H15A H 0.1432 -0.4875 0.0377 0.068 Uiso 1 1 calc R . .
H15B H 0.1237 -0.3494 0.0803 0.068 Uiso 1 1 calc R . .
H15C H 0.0603 -0.4529 0.0280 0.068 Uiso 1 1 calc R . .
O4 O 0.44503(14) -0.4218(3) 0.38121(17) 0.0575(8) Uani 1 1 d . . .
O5 O 0.43791(13) -0.2195(3) 0.43505(15) 0.0480(7) Uani 1 1 d . . .
O6 O 0.24900(13) -0.3826(2) 0.35301(15) 0.0432(6) Uani 1 1 d . . .
N3 N 0.43160(14) -0.2973(3) 0.37399(18) 0.0353(7) Uani 1 1 d . . .
N4 N 0.28853(13) -0.1829(3) 0.31193(16) 0.0309(6) Uani 1 1 d . . .
H1A H 0.2846 -0.0911 0.3142 0.037 Uiso 1 1 d R . .
C16 C 0.40408(16) -0.2388(3) 0.28328(19) 0.0295(8) Uani 1 1 d . . .
H16 H 0.4225 -0.2985 0.2445 0.035 Uiso 1 1 calc R . .
C17 C 0.32019(16) -0.2458(3) 0.2517(2) 0.0304(7) Uani 1 1 d . . .
H17 H 0.3051 -0.3454 0.2437 0.036 Uiso 1 1 calc R . .
C18 C 0.25329(16) -0.2553(3) 0.35652(19) 0.0295(7) Uani 1 1 d . . .
C19 C 0.21847(17) -0.1712(3) 0.4104(2) 0.0365(8) Uani 1 1 d . . .
H19A H 0.1655 -0.1816 0.3873 0.055 Uiso 1 1 calc R . .
H19B H 0.2314 -0.0732 0.4085 0.055 Uiso 1 1 calc R . .
H19C H 0.2359 -0.2041 0.4706 0.055 Uiso 1 1 calc R . .
C20 C 0.29143(17) -0.1734(4) 0.1655(2) 0.0358(8) Uani 1 1 d . . .
H20 H 0.2434 -0.1952 0.1298 0.043 Uiso 1 1 calc R . .
C21 C 0.32797(18) -0.0822(4) 0.1360(2) 0.0400(9) Uani 1 1 d . . .
C22 C 0.40612(18) -0.0472(4) 0.1834(2) 0.0414(9) Uani 1 1 d . . .
H22A H 0.4129 0.0543 0.1800 0.050 Uiso 1 1 calc R . .
H22B H 0.4374 -0.0935 0.1540 0.050 Uiso 1 1 calc R . .
C23 C 0.43106(15) -0.0914(3) 0.2797(2) 0.0310(8) Uani 1 1 d . . .
H23 H 0.4067 -0.0295 0.3113 0.037 Uiso 1 1 calc R . .
C24 C 0.51294(16) -0.0753(3) 0.3209(2) 0.0320(8) Uani 1 1 d . . .
C25 C 0.56130(17) -0.1484(4) 0.2907(2) 0.0395(9) Uani 1 1 d . . .
H25 H 0.5429 -0.2107 0.2434 0.047 Uiso 1 1 calc R . .
C26 C 0.63578(18) -0.1329(4) 0.3276(2) 0.0465(10) Uani 1 1 d . . .
H26 H 0.6680 -0.1843 0.3059 0.056 Uiso 1 1 calc R . .
C27 C 0.66304(19) -0.0420(4) 0.3964(2) 0.0477(10) Uani 1 1 d . . .
H27 H 0.7141 -0.0299 0.4218 0.057 Uiso 1 1 calc R . .
C28 C 0.61583(18) 0.0306(4) 0.4277(2) 0.0444(9) Uani 1 1 d . . .
H28 H 0.6345 0.0924 0.4752 0.053 Uiso 1 1 calc R . .
C29 C 0.54138(18) 0.0144(3) 0.3907(2) 0.0376(9) Uani 1 1 d . . .
H29 H 0.5094 0.0650 0.4131 0.045 Uiso 1 1 calc R . .
C30 C 0.2954(2) -0.0067(4) 0.0510(2) 0.0585(12) Uani 1 1 d . . .
H30A H 0.2444 -0.0346 0.0248 0.088 Uiso 1 1 calc R . .
H30B H 0.3226 -0.0300 0.0116 0.088 Uiso 1 1 calc R . .
H30C H 0.2979 0.0936 0.0615 0.088 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.220(3) . ?
O2 N1 1.221(3) . ?
O3 C3 1.235(4) . ?
N1 C1 1.514(4) . ?
N2 C3 1.345(4) . ?
N2 C2 1.465(4) . ?
N2 H2A 0.8352 . ?
C1 C8 1.512(4) . ?
C1 C2 1.535(4) . ?
C1 H1 1.0000 . ?
C2 C5 1.503(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.492(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.326(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.491(5) . ?
C6 C15 1.509(5) . ?
C7 C8 1.543(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.511(4) . ?
C8 H8 1.0000 . ?
C9 C10 1.383(4) . ?
C9 C14 1.392(4) . ?
C10 C11 1.384(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O4 N3 1.225(3) . ?
O5 N3 1.219(3) . ?
O6 C18 1.230(4) . ?
N3 C16 1.508(4) . ?
N4 C18 1.341(4) . ?
N4 C17 1.446(4) . ?
N4 H1A 0.8895 . ?
C16 C23 1.521(4) . ?
C16 C17 1.543(4) . ?
C16 H16 1.0000 . ?
C17 C20 1.503(4) . ?
C17 H17 1.0000 . ?
C18 C19 1.504(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.312(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.502(4) . ?
C21 C30 1.510(5) . ?
C22 C23 1.544(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.521(4) . ?
C23 H23 1.0000 . ?
C24 C25 1.384(4) . ?
C24 C29 1.392(4) . ?
C25 C26 1.383(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.386(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.374(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.383(5) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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
O1 N1 O2 123.7(3) . . ?
O1 N1 C1 119.5(3) . . ?
O2 N1 C1 116.8(3) . . ?
C3 N2 C2 122.3(3) . . ?
C3 N2 H2A 120.7 . . ?
C2 N2 H2A 116.1 . . ?
C8 C1 N1 111.6(3) . . ?
C8 C1 C2 113.6(3) . . ?
N1 C1 C2 107.6(2) . . ?
C8 C1 H1 108.0 . . ?
N1 C1 H1 108.0 . . ?
C2 C1 H1 108.0 . . ?
N2 C2 C5 110.7(3) . . ?
N2 C2 C1 113.9(3) . . ?
C5 C2 C1 109.5(3) . . ?
N2 C2 H2 107.5 . . ?
C5 C2 H2 107.5 . . ?
C1 C2 H2 107.5 . . ?
O3 C3 N2 121.7(3) . . ?
O3 C3 C4 121.7(3) . . ?
N2 C3 C4 116.6(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C2 124.8(3) . . ?
C6 C5 H5 117.6 . . ?
C2 C5 H5 117.6 . . ?
C5 C6 C7 121.8(3) . . ?
C5 C6 C15 122.5(3) . . ?
C7 C6 C15 115.7(3) . . ?
C6 C7 C8 115.0(3) . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C1 114.2(3) . . ?
C9 C8 C7 110.3(3) . . ?
C1 C8 C7 107.2(3) . . ?
C9 C8 H8 108.3 . . ?
C1 C8 H8 108.3 . . ?
C7 C8 H8 108.3 . . ?
C10 C9 C14 117.2(3) . . ?
C10 C9 C8 122.2(3) . . ?
C14 C9 C8 120.5(3) . . ?
C11 C10 C9 122.0(3) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 119.7(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 119.8(4) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 N3 O5 124.2(3) . . ?
O4 N3 C16 117.2(3) . . ?
O5 N3 C16 118.6(3) . . ?
C18 N4 C17 123.4(3) . . ?
C18 N4 H1A 115.4 . . ?
C17 N4 H1A 120.3 . . ?
N3 C16 C23 111.6(2) . . ?
N3 C16 C17 108.3(3) . . ?
C23 C16 C17 111.5(2) . . ?
N3 C16 H16 108.4 . . ?
C23 C16 H16 108.4 . . ?
C17 C16 H16 108.4 . . ?
N4 C17 C20 109.1(3) . . ?
N4 C17 C16 112.8(2) . . ?
C20 C17 C16 109.0(3) . . ?
N4 C17 H17 108.6 . . ?
C20 C17 H17 108.6 . . ?
C16 C17 H17 108.6 . . ?
O6 C18 N4 122.1(3) . . ?
O6 C18 C19 121.9(3) . . ?
N4 C18 C19 116.0(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C17 124.7(3) . . ?
C21 C20 H20 117.7 . . ?
C17 C20 H20 117.7 . . ?
C20 C21 C22 122.5(3) . . ?
C20 C21 C30 122.7(3) . . ?
C22 C21 C30 114.7(3) . . ?
C21 C22 C23 113.2(3) . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.8 . . ?
C24 C23 C16 113.7(2) . . ?
C24 C23 C22 111.2(3) . . ?
C16 C23 C22 107.3(3) . . ?
C24 C23 H23 108.2 . . ?
C16 C23 H23 108.2 . . ?
C22 C23 H23 108.2 . . ?
C25 C24 C29 118.0(3) . . ?
C25 C24 C23 121.5(3) . . ?
C29 C24 C23 120.5(3) . . ?
C24 C25 C26 121.6(3) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C27 C26 C25 119.5(3) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C28 C27 C26 119.6(3) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C29 120.6(3) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C28 C29 C24 120.7(3) . . ?
C28 C29 H29 119.7 . . ?
C24 C29 H29 119.7 . . ?
C21 C30 H30A 109.5 . . ?
C21 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C21 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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 N1 C1 C8 -27.1(4) . . . . ?
O2 N1 C1 C8 155.0(3) . . . . ?
O1 N1 C1 C2 98.1(3) . . . . ?
O2 N1 C1 C2 -79.8(3) . . . . ?
C3 N2 C2 C5 -115.1(3) . . . . ?
C3 N2 C2 C1 121.0(3) . . . . ?
C8 C1 C2 N2 76.9(3) . . . . ?
N1 C1 C2 N2 -47.1(3) . . . . ?
C8 C1 C2 C5 -47.6(3) . . . . ?
N1 C1 C2 C5 -171.7(2) . . . . ?
C2 N2 C3 O3 -3.5(5) . . . . ?
C2 N2 C3 C4 176.2(3) . . . . ?
N2 C2 C5 C6 -109.5(4) . . . . ?
C1 C2 C5 C6 16.8(4) . . . . ?
C2 C5 C6 C7 -1.7(5) . . . . ?
C2 C5 C6 C15 179.7(3) . . . . ?
C5 C6 C7 C8 15.9(5) . . . . ?
C15 C6 C7 C8 -165.4(3) . . . . ?
N1 C1 C8 C9 -54.5(3) . . . . ?
C2 C1 C8 C9 -176.4(3) . . . . ?
N1 C1 C8 C7 -177.1(3) . . . . ?
C2 C1 C8 C7 61.1(3) . . . . ?
C6 C7 C8 C9 -168.6(3) . . . . ?
C6 C7 C8 C1 -43.6(4) . . . . ?
C1 C8 C9 C10 -53.2(4) . . . . ?
C7 C8 C9 C10 67.7(4) . . . . ?
C1 C8 C9 C14 130.1(3) . . . . ?
C7 C8 C9 C14 -109.1(3) . . . . ?
C14 C9 C10 C11 -0.8(5) . . . . ?
C8 C9 C10 C11 -177.7(3) . . . . ?
C9 C10 C11 C12 0.7(5) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?
C11 C12 C13 C14 -0.4(5) . . . . ?
C12 C13 C14 C9 0.2(5) . . . . ?
C10 C9 C14 C13 0.4(5) . . . . ?
C8 C9 C14 C13 177.3(3) . . . . ?
O4 N3 C16 C23 -145.8(3) . . . . ?
O5 N3 C16 C23 35.4(4) . . . . ?
O4 N3 C16 C17 91.0(3) . . . . ?
O5 N3 C16 C17 -87.8(3) . . . . ?
C18 N4 C17 C20 126.1(3) . . . . ?
C18 N4 C17 C16 -112.6(3) . . . . ?
N3 C16 C17 N4 52.3(3) . . . . ?
C23 C16 C17 N4 -70.9(3) . . . . ?
N3 C16 C17 C20 173.7(3) . . . . ?
C23 C16 C17 C20 50.5(3) . . . . ?
C17 N4 C18 O6 4.3(4) . . . . ?
C17 N4 C18 C19 -175.0(2) . . . . ?
N4 C17 C20 C21 103.3(4) . . . . ?
C16 C17 C20 C21 -20.3(5) . . . . ?
C17 C20 C21 C22 4.6(6) . . . . ?
C17 C20 C21 C30 -176.7(3) . . . . ?
C20 C21 C22 C23 -17.9(5) . . . . ?
C30 C21 C22 C23 163.4(3) . . . . ?
N3 C16 C23 C24 51.2(4) . . . . ?
C17 C16 C23 C24 172.5(3) . . . . ?
N3 C16 C23 C22 174.6(3) . . . . ?
C17 C16 C23 C22 -64.1(3) . . . . ?
C21 C22 C23 C24 170.8(3) . . . . ?
C21 C22 C23 C16 45.9(4) . . . . ?
C16 C23 C24 C25 60.0(4) . . . . ?
C22 C23 C24 C25 -61.2(4) . . . . ?
C16 C23 C24 C29 -120.1(3) . . . . ?
C22 C23 C24 C29 118.7(3) . . . . ?
C29 C24 C25 C26 -0.5(5) . . . . ?
C23 C24 C25 C26 179.4(3) . . . . ?
C24 C25 C26 C27 -0.2(6) . . . . ?
C25 C26 C27 C28 0.7(6) . . . . ?
C26 C27 C28 C29 -0.5(6) . . . . ?
C27 C28 C29 C24 -0.2(5) . . . . ?
C25 C24 C29 C28 0.7(5) . . . . ?
C23 C24 C29 C28 -179.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.915
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.915
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 973121'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_akwe269_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 N2 O3'
_chemical_formula_sum            'C15 H18 N2 O3'
_chemical_formula_weight         274.31

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           monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.0719(12)
_cell_length_b                   5.2738(3)
_cell_length_c                   27.2994(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.632(4)
_cell_angle_gamma                90.00
_cell_volume                     2745.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7864
_cell_measurement_theta_min      1.49
_cell_measurement_theta_max      27.00
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .07
_exptl_crystal_size_min          .03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.093
_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  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/Omega-Scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7864
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3000
_reflns_number_gt                1938
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius COLLECT'
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2004)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0693P)²+0.7113P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3000
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1300
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_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 0.16795(9) 1.2672(3) 0.13160(5) 0.0409(4) Uani 1 1 d . . .
O2 O 0.23949(8) 0.9603(3) 0.11791(6) 0.0486(5) Uani 1 1 d . . .
O3 O 0.13969(8) 1.2996(3) 0.01176(5) 0.0332(4) Uani 1 1 d . . .
N1 N 0.18035(9) 1.0443(3) 0.12277(6) 0.0297(4) Uani 1 1 d . . .
N2 N 0.12442(9) 0.8825(4) 0.02754(6) 0.0269(4) Uani 1 1 d . . .
C1 C 0.12052(11) 0.8611(4) 0.11767(7) 0.0320(5) Uani 1 1 d . . .
H1 H 0.1398 0.6851 0.1155 0.038 Uiso 1 1 calc R . .
C2 C 0.08011(11) 0.9222(4) 0.06974(7) 0.0283(5) Uani 1 1 d . . .
H2 H 0.0652 1.1039 0.0705 0.034 Uiso 1 1 calc R . .
C3 C 0.15088(11) 1.0768(4) 0.00080(7) 0.0274(5) Uani 1 1 d . . .
C4 C 0.19345(11) 1.0031(5) -0.04269(7) 0.0374(6) Uani 1 1 d . . .
H4A H 0.1710 1.0684 -0.0726 0.056 Uiso 1 1 calc R . .
H4B H 0.1965 0.8178 -0.0446 0.056 Uiso 1 1 calc R . .
H4C H 0.2407 1.0746 -0.0394 0.056 Uiso 1 1 calc R . .
C5 C 0.01599(11) 0.7580(4) 0.06701(7) 0.0292(5) Uani 1 1 d . . .
H5 H -0.0063 0.7392 0.0359 0.035 Uiso 1 1 calc R . .
C6 C -0.01224(11) 0.6364(4) 0.10478(7) 0.0272(5) Uani 1 1 d . . .
C7 C 0.01776(11) 0.6638(4) 0.15594(7) 0.0287(5) Uani 1 1 d . . .
H7A H 0.0400 0.5016 0.1657 0.034 Uiso 1 1 calc R . .
H7B H -0.0211 0.6970 0.1788 0.034 Uiso 1 1 calc R . .
C8 C 0.07195(11) 0.8766(4) 0.16097(7) 0.0324(5) Uani 1 1 d . . .
H8 H 0.0458 1.0401 0.1578 0.039 Uiso 1 1 calc R . .
C9 C 0.10858(11) 0.8812(4) 0.21058(7) 0.0289(5) Uani 1 1 d . . .
C10 C 0.09463(12) 1.0765(4) 0.24305(8) 0.0358(6) Uani 1 1 d . . .
H10 H 0.0624 1.2059 0.2338 0.043 Uiso 1 1 calc R . .
C11 C 0.12696(13) 1.0859(5) 0.28872(8) 0.0395(6) Uani 1 1 d . . .
H11 H 0.1166 1.2210 0.3105 0.047 Uiso 1 1 calc R . .
C12 C 0.17390(12) 0.9010(4) 0.30269(7) 0.0346(5) Uani 1 1 d . . .
H12 H 0.1959 0.9078 0.3340 0.042 Uiso 1 1 calc R . .
C13 C 0.18876(12) 0.7058(5) 0.27094(8) 0.0354(5) Uani 1 1 d . . .
H13 H 0.2212 0.5776 0.2804 0.043 Uiso 1 1 calc R . .
C14 C 0.15663(12) 0.6956(4) 0.22512(8) 0.0341(5) Uani 1 1 d . . .
H14 H 0.1675 0.5607 0.2034 0.041 Uiso 1 1 calc R . .
C15 C -0.07414(11) 0.4639(5) 0.09893(7) 0.0355(5) Uani 1 1 d . . .
H15A H -0.0905 0.4672 0.0648 0.053 Uiso 1 1 calc R . .
H15B H -0.1119 0.5210 0.1203 0.053 Uiso 1 1 calc R . .
H15C H -0.0605 0.2906 0.1078 0.053 Uiso 1 1 calc R . .
H1A H 0.1326(11) 0.733(5) 0.0189(7) 0.027(6) Uiso 1 1 d . . .


_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 N1 1.223(2) . ?
O2 N1 1.220(2) . ?
O3 C3 1.232(2) . ?
N1 C1 1.501(3) . ?
N2 C3 1.358(3) . ?
N2 C2 1.451(3) . ?
N2 H1A 0.84(2) . ?
C1 C8 1.512(3) . ?
C1 C2 1.545(3) . ?
C1 H1 1.0000 . ?
C2 C5 1.500(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.497(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.333(3) . ?
C5 H5 0.9500 . ?
C6 C15 1.498(3) . ?
C6 C7 1.510(3) . ?
C7 C8 1.531(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.517(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.387(3) . ?
C9 C14 1.396(3) . ?
C10 C11 1.386(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
O2 N1 O1 123.45(18) . . ?
O2 N1 C1 117.32(18) . . ?
O1 N1 C1 119.24(19) . . ?
C3 N2 C2 122.75(19) . . ?
C3 N2 H1A 119.2(14) . . ?
C2 N2 H1A 118.0(14) . . ?
N1 C1 C8 111.37(16) . . ?
N1 C1 C2 108.42(16) . . ?
C8 C1 C2 110.28(18) . . ?
N1 C1 H1 108.9 . . ?
C8 C1 H1 108.9 . . ?
C2 C1 H1 108.9 . . ?
N2 C2 C5 111.05(16) . . ?
N2 C2 C1 110.66(17) . . ?
C5 C2 C1 108.69(16) . . ?
N2 C2 H2 108.8 . . ?
C5 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
O3 C3 N2 121.50(19) . . ?
O3 C3 C4 122.51(19) . . ?
N2 C3 C4 115.99(19) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C2 125.14(18) . . ?
C6 C5 H5 117.4 . . ?
C2 C5 H5 117.4 . . ?
C5 C6 C15 122.30(18) . . ?
C5 C6 C7 121.14(19) . . ?
C15 C6 C7 116.56(17) . . ?
C6 C7 C8 113.68(17) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C1 C8 C9 114.76(18) . . ?
C1 C8 C7 108.01(17) . . ?
C9 C8 C7 113.30(17) . . ?
C1 C8 H8 106.8 . . ?
C9 C8 H8 106.8 . . ?
C7 C8 H8 106.8 . . ?
C10 C9 C14 117.98(19) . . ?
C10 C9 C8 119.5(2) . . ?
C14 C9 C8 122.49(19) . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.7(2) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O2 N1 C1 C8 128.26(19) . . . . ?
O1 N1 C1 C8 -51.5(2) . . . . ?
O2 N1 C1 C2 -110.2(2) . . . . ?
O1 N1 C1 C2 70.0(2) . . . . ?
C3 N2 C2 C5 131.7(2) . . . . ?
C3 N2 C2 C1 -107.5(2) . . . . ?
N1 C1 C2 N2 63.7(2) . . . . ?
C8 C1 C2 N2 -174.16(17) . . . . ?
N1 C1 C2 C5 -174.15(16) . . . . ?
C8 C1 C2 C5 -52.0(2) . . . . ?
C2 N2 C3 O3 1.6(3) . . . . ?
C2 N2 C3 C4 -177.82(17) . . . . ?
N2 C2 C5 C6 139.7(2) . . . . ?
C1 C2 C5 C6 17.7(3) . . . . ?
C2 C5 C6 C15 -176.6(2) . . . . ?
C2 C5 C6 C7 2.6(3) . . . . ?
C5 C6 C7 C8 11.1(3) . . . . ?
C15 C6 C7 C8 -169.72(18) . . . . ?
N1 C1 C8 C9 -46.0(3) . . . . ?
C2 C1 C8 C9 -166.37(18) . . . . ?
N1 C1 C8 C7 -173.39(17) . . . . ?
C2 C1 C8 C7 66.2(2) . . . . ?
C6 C7 C8 C1 -44.3(2) . . . . ?
C6 C7 C8 C9 -172.59(18) . . . . ?
C1 C8 C9 C10 125.3(2) . . . . ?
C7 C8 C9 C10 -110.0(2) . . . . ?
C1 C8 C9 C14 -54.4(3) . . . . ?
C7 C8 C9 C14 70.3(3) . . . . ?
C14 C9 C10 C11 -0.5(3) . . . . ?
C8 C9 C10 C11 179.7(2) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C9 -0.4(3) . . . . ?
C10 C9 C14 C13 0.6(3) . . . . ?
C8 C9 C14 C13 -179.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 973122'
