# Electronic Supplementary Material (ESI) for ChemComm.
# 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.
#
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#  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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# 
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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_x057

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 N2 O5'
_chemical_formula_weight         370.40

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.199(3)
_cell_length_b                   12.840(3)
_cell_length_c                   14.621(3)
_cell_angle_alpha                100.605(4)
_cell_angle_beta                 114.357(4)
_cell_angle_gamma                104.026(4)
_cell_volume                     1916.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2302
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      21.87

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Bruker APEX 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            9748
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         25.03
_reflns_number_total             6679
_reflns_number_gt                4687
_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 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)+(0.0915P)²+0.4450P] 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         6679
_refine_ls_number_parameters     493
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1780
_refine_ls_wR_factor_gt          0.1560
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.005
_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 0.7962(3) 0.1457(3) 0.0711(2) 0.0552(7) Uani 1 1 d . . .
C2 C 0.7649(3) 0.1434(3) -0.0324(2) 0.0754(10) Uani 1 1 d . . .
H2 H 0.6965 0.0841 -0.0903 0.091 Uiso 1 1 calc R . .
C3 C 0.8404(4) 0.2336(4) -0.0453(3) 0.0892(12) Uani 1 1 d . . .
H3 H 0.8217 0.2345 -0.1136 0.107 Uiso 1 1 calc R . .
C4 C 0.9418(4) 0.3213(3) 0.0398(3) 0.0835(11) Uani 1 1 d . . .
H4 H 0.9902 0.3802 0.0280 0.100 Uiso 1 1 calc R . .
C5 C 0.9730(3) 0.3237(3) 0.1423(3) 0.0672(8) Uani 1 1 d . . .
H5 H 1.0420 0.3832 0.1996 0.081 Uiso 1 1 calc R . .
C6 C 0.8993(3) 0.2351(2) 0.1586(2) 0.0532(7) Uani 1 1 d . . .
C7 C 0.9023(3) 0.2123(2) 0.2519(2) 0.0500(7) Uani 1 1 d . . .
H7 H 0.9604 0.2584 0.3213 0.060 Uiso 1 1 calc R . .
C8 C 0.8077(2) 0.1136(2) 0.22314(19) 0.0457(6) Uani 1 1 d . . .
C9 C 0.6346(3) -0.0317(3) 0.0511(2) 0.0624(8) Uani 1 1 d . . .
C10 C 0.5934(3) -0.0973(3) 0.1131(2) 0.0690(9) Uani 1 1 d . . .
H10A H 0.6335 -0.1541 0.1210 0.083 Uiso 1 1 calc R . .
H10B H 0.5009 -0.1369 0.0730 0.083 Uiso 1 1 calc R . .
C11 C 0.6268(3) -0.0254(3) 0.2224(2) 0.0632(8) Uani 1 1 d . . .
H11A H 0.6055 -0.0749 0.2601 0.076 Uiso 1 1 calc R . .
H11B H 0.5750 0.0222 0.2147 0.076 Uiso 1 1 calc R . .
C12 C 0.7700(3) 0.0499(2) 0.2883(2) 0.0521(7) Uani 1 1 d . . .
C13 C 0.7916(3) 0.1396(3) 0.3881(2) 0.0759(10) Uani 1 1 d . . .
H13A H 0.8836 0.1788 0.4330 0.091 Uiso 1 1 calc R . .
H13B H 0.7554 0.1952 0.3646 0.091 Uiso 1 1 calc R . .
C14 C 0.7377(4) 0.0981(4) 0.4535(3) 0.1035(13) Uani 1 1 d . . .
H14A H 0.6463 0.0599 0.4108 0.155 Uiso 1 1 calc R . .
H14B H 0.7555 0.1610 0.5110 0.155 Uiso 1 1 calc R . .
H14C H 0.7763 0.0464 0.4813 0.155 Uiso 1 1 calc R . .
C15 C 0.8508(3) -0.0271(2) 0.3203(2) 0.0574(7) Uani 1 1 d . . .
H15A H 0.8490 -0.0438 0.3819 0.069 Uiso 1 1 calc R . .
H15B H 0.8097 -0.0983 0.2629 0.069 Uiso 1 1 calc R . .
C16 C 0.9888(3) 0.0222(2) 0.3455(2) 0.0540(7) Uani 1 1 d . . .
C17 C 1.0224(3) -0.0058(2) 0.2587(2) 0.0526(7) Uani 1 1 d . . .
C18 C 0.8708(4) -0.1462(4) -0.0107(3) 0.1027(14) Uani 1 1 d . . .
H18A H 0.8229 -0.2179 -0.0112 0.154 Uiso 1 1 calc R . .
H18B H 0.9030 -0.1586 -0.0600 0.154 Uiso 1 1 calc R . .
H18C H 0.8157 -0.1032 -0.0307 0.154 Uiso 1 1 calc R . .
C19 C 1.1608(3) 0.0406(3) 0.2846(2) 0.0605(8) Uani 1 1 d . . .
C20 C 1.3578(3) 0.0107(4) 0.3507(4) 0.1054(14) Uani 1 1 d . . .
H20A H 1.3671 0.0111 0.2886 0.158 Uiso 1 1 calc R . .
H20B H 1.3947 -0.0404 0.3815 0.158 Uiso 1 1 calc R . .
H20C H 1.4014 0.0857 0.4011 0.158 Uiso 1 1 calc R . .
C21 C 0.5079(3) 0.5760(3) 0.2159(2) 0.0555(7) Uani 1 1 d . . .
C22 C 0.3744(3) 0.5363(3) 0.1757(3) 0.0737(9) Uani 1 1 d . . .
H22 H 0.3203 0.4731 0.1157 0.088 Uiso 1 1 calc R . .
C23 C 0.3272(4) 0.5953(4) 0.2293(4) 0.0911(12) Uani 1 1 d . . .
H23 H 0.2388 0.5709 0.2048 0.109 Uiso 1 1 calc R . .
C24 C 0.4066(5) 0.6901(4) 0.3189(4) 0.0973(13) Uani 1 1 d . . .
H24 H 0.3705 0.7279 0.3525 0.117 Uiso 1 1 calc R . .
C25 C 0.5383(4) 0.7289(3) 0.3586(3) 0.0812(10) Uani 1 1 d . . .
H25 H 0.5915 0.7923 0.4186 0.097 Uiso 1 1 calc R . .
C26 C 0.5901(3) 0.6701(3) 0.3061(2) 0.0573(7) Uani 1 1 d . . .
C27 C 0.7195(3) 0.6853(2) 0.3265(2) 0.0537(7) Uani 1 1 d . . .
H27 H 0.7934 0.7425 0.3817 0.064 Uiso 1 1 calc R . .
C28 C 0.7164(2) 0.6027(2) 0.25215(19) 0.0437(6) Uani 1 1 d . . .
C29 C 0.5438(3) 0.4392(3) 0.0951(2) 0.0545(7) Uani 1 1 d . . .
C30 C 0.6471(3) 0.4109(3) 0.0782(2) 0.0590(7) Uani 1 1 d . . .
H30A H 0.6146 0.3784 0.0026 0.071 Uiso 1 1 calc R . .
H30B H 0.6657 0.3534 0.1104 0.071 Uiso 1 1 calc R . .
C31 C 0.7722(3) 0.5106(2) 0.1227(2) 0.0519(7) Uani 1 1 d . . .
H31A H 0.7578 0.5620 0.0817 0.062 Uiso 1 1 calc R . .
H31B H 0.8363 0.4829 0.1153 0.062 Uiso 1 1 calc R . .
C32 C 0.8243(2) 0.5759(2) 0.23999(19) 0.0434(6) Uani 1 1 d . . .
C33 C 0.9342(3) 0.6883(2) 0.2739(2) 0.0573(7) Uani 1 1 d . . .
H33A H 0.8976 0.7376 0.2380 0.069 Uiso 1 1 calc R . .
H33B H 0.9702 0.7247 0.3494 0.069 Uiso 1 1 calc R . .
C34 C 1.0433(3) 0.6791(3) 0.2517(3) 0.0715(9) Uani 1 1 d . . .
H34A H 1.0805 0.6302 0.2862 0.107 Uiso 1 1 calc R . .
H34B H 1.1079 0.7529 0.2781 0.107 Uiso 1 1 calc R . .
H34C H 1.0104 0.6483 0.1766 0.107 Uiso 1 1 calc R . .
C35 C 0.8754(2) 0.5024(2) 0.31049(19) 0.0418(6) Uani 1 1 d . . .
H35A H 0.8240 0.4230 0.2710 0.050 Uiso 1 1 calc R . .
H35B H 0.9635 0.5132 0.3259 0.050 Uiso 1 1 calc R . .
C36 C 0.8712(2) 0.5313(2) 0.41265(19) 0.0417(6) Uani 1 1 d . . .
C37 C 0.7540(2) 0.4662(2) 0.41572(19) 0.0419(6) Uani 1 1 d . . .
C38 C 0.4607(3) 0.2558(3) 0.2427(2) 0.0796(11) Uani 1 1 d . . .
H38A H 0.4304 0.2971 0.1951 0.119 Uiso 1 1 calc R . .
H38B H 0.3910 0.2136 0.2513 0.119 Uiso 1 1 calc R . .
H38C H 0.4929 0.2045 0.2141 0.119 Uiso 1 1 calc R . .
C39 C 0.7456(2) 0.4990(2) 0.5163(2) 0.0491(6) Uani 1 1 d . . .
C40 C 0.6594(4) 0.6009(3) 0.6014(3) 0.0901(12) Uani 1 1 d . . .
H40A H 0.6266 0.5359 0.6188 0.135 Uiso 1 1 calc R . .
H40B H 0.5991 0.6397 0.5849 0.135 Uiso 1 1 calc R . .
H40C H 0.7402 0.6511 0.6608 0.135 Uiso 1 1 calc R . .
N1 N 0.7389(2) 0.06937(19) 0.11024(16) 0.0527(6) Uani 1 1 d . . .
N2 N 0.9313(2) -0.0663(2) 0.16543(19) 0.0581(6) Uani 1 1 d . . .
N3 N 0.5860(2) 0.53327(19) 0.18217(16) 0.0478(5) Uani 1 1 d . . .
N4 N 0.6661(2) 0.38596(18) 0.33176(16) 0.0477(5) Uani 1 1 d . . .
O1 O 0.5835(2) -0.0632(2) -0.04508(16) 0.0845(7) Uani 1 1 d . . .
O2 O 1.07489(19) 0.0843(2) 0.43235(16) 0.0730(6) Uani 1 1 d . . .
O3 O 0.9773(2) -0.0846(2) 0.09448(17) 0.0772(7) Uani 1 1 d . . .
O4 O 1.2070(2) 0.1256(2) 0.2719(2) 0.0973(8) Uani 1 1 d . . .
O5 O 1.2224(2) -0.0259(2) 0.3215(2) 0.0806(7) Uani 1 1 d . . .
O6 O 0.4299(2) 0.3844(2) 0.03864(17) 0.0757(6) Uani 1 1 d . . .
O7 O 0.95633(18) 0.60689(16) 0.49200(14) 0.0599(5) Uani 1 1 d . . .
O8 O 0.56153(17) 0.33340(16) 0.34337(15) 0.0598(5) Uani 1 1 d . . .
O9 O 0.7947(2) 0.4680(2) 0.59004(17) 0.0837(7) Uani 1 1 d . . .
O10 O 0.6777(2) 0.56471(18) 0.51053(15) 0.0656(6) Uani 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
C1 C2 1.392(4) . ?
C1 N1 1.407(4) . ?
C1 C6 1.403(4) . ?
C2 C3 1.390(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.435(4) . ?
C7 C8 1.344(4) . ?
C7 H7 0.9300 . ?
C8 N1 1.426(3) . ?
C8 C12 1.502(4) . ?
C9 O1 1.215(3) . ?
C9 N1 1.389(4) . ?
C9 C10 1.495(5) . ?
C10 C11 1.520(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.538(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C15 1.558(4) . ?
C12 C13 1.562(4) . ?
C13 C14 1.472(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.502(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O2 1.214(3) . ?
C16 C17 1.497(4) . ?
C17 N2 1.280(3) . ?
C17 C19 1.500(4) . ?
C18 O3 1.444(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O4 1.185(3) . ?
C19 O5 1.316(4) . ?
C20 O5 1.449(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C26 1.392(4) . ?
C21 C22 1.398(4) . ?
C21 N3 1.413(3) . ?
C22 C23 1.372(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.390(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.379(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.406(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.436(4) . ?
C27 C28 1.352(4) . ?
C27 H27 0.9300 . ?
C28 N3 1.416(3) . ?
C28 C32 1.507(3) . ?
C29 O6 1.214(3) . ?
C29 N3 1.392(4) . ?
C29 C30 1.492(4) . ?
C30 C31 1.522(4) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.536(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.542(4) . ?
C32 C35 1.567(3) . ?
C33 C34 1.519(4) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C36 1.496(3) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 O7 1.212(3) . ?
C36 C37 1.494(3) . ?
C37 N4 1.277(3) . ?
C37 C39 1.506(3) . ?
C38 O8 1.430(3) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 O9 1.191(3) . ?
C39 O10 1.309(3) . ?
C40 O10 1.449(4) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
N2 O3 1.379(3) . ?
N4 O8 1.384(3) . ?

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
C2 C1 N1 130.8(3) . . ?
C2 C1 C6 121.6(3) . . ?
N1 C1 C6 107.6(2) . . ?
C1 C2 C3 117.1(3) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 121.1(4) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 118.7(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 C7 133.4(3) . . ?
C1 C6 C7 107.0(2) . . ?
C8 C7 C6 109.2(2) . . ?
C8 C7 H7 125.4 . . ?
C6 C7 H7 125.4 . . ?
C7 C8 N1 108.5(2) . . ?
C7 C8 C12 131.1(2) . . ?
N1 C8 C12 120.4(2) . . ?
O1 C9 N1 120.3(3) . . ?
O1 C9 C10 123.6(3) . . ?
N1 C9 C10 116.0(3) . . ?
C9 C10 C11 114.3(3) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 C12 112.6(2) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C8 C12 C11 109.0(2) . . ?
C8 C12 C15 110.9(2) . . ?
C11 C12 C15 108.7(2) . . ?
C8 C12 C13 107.3(2) . . ?
C11 C12 C13 109.7(2) . . ?
C15 C12 C13 111.3(2) . . ?
C14 C13 C12 117.4(3) . . ?
C14 C13 H13A 108.0 . . ?
C12 C13 H13A 108.0 . . ?
C14 C13 H13B 108.0 . . ?
C12 C13 H13B 108.0 . . ?
H13A C13 H13B 107.2 . . ?
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 . . ?
C16 C15 C12 115.1(2) . . ?
C16 C15 H15A 108.5 . . ?
C12 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
C12 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
O2 C16 C17 117.9(3) . . ?
O2 C16 C15 123.6(3) . . ?
C17 C16 C15 118.5(2) . . ?
N2 C17 C16 118.4(3) . . ?
N2 C17 C19 123.2(3) . . ?
C16 C17 C19 118.4(2) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 O5 125.0(3) . . ?
O4 C19 C17 123.8(3) . . ?
O5 C19 C17 111.1(3) . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 122.3(3) . . ?
C26 C21 N3 107.0(2) . . ?
C22 C21 N3 130.7(3) . . ?
C23 C22 C21 116.6(4) . . ?
C23 C22 H22 121.7 . . ?
C21 C22 H22 121.7 . . ?
C22 C23 C24 122.4(4) . . ?
C22 C23 H23 118.8 . . ?
C24 C23 H23 118.8 . . ?
C25 C24 C23 120.8(4) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 118.3(4) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
C21 C26 C25 119.5(3) . . ?
C21 C26 C27 107.7(2) . . ?
C25 C26 C27 132.8(3) . . ?
C28 C27 C26 108.8(3) . . ?
C28 C27 H27 125.6 . . ?
C26 C27 H27 125.6 . . ?
C27 C28 N3 108.1(2) . . ?
C27 C28 C32 130.6(2) . . ?
N3 C28 C32 121.3(2) . . ?
O6 C29 N3 120.9(3) . . ?
O6 C29 C30 123.5(3) . . ?
N3 C29 C30 115.6(2) . . ?
C29 C30 C31 115.0(2) . . ?
C29 C30 H30A 108.5 . . ?
C31 C30 H30A 108.5 . . ?
C29 C30 H30B 108.5 . . ?
C31 C30 H30B 108.5 . . ?
H30A C30 H30B 107.5 . . ?
C30 C31 C32 112.6(2) . . ?
C30 C31 H31A 109.1 . . ?
C32 C31 H31A 109.1 . . ?
C30 C31 H31B 109.1 . . ?
C32 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?
C28 C32 C31 108.1(2) . . ?
C28 C32 C33 108.6(2) . . ?
C31 C32 C33 109.9(2) . . ?
C28 C32 C35 110.72(19) . . ?
C31 C32 C35 109.9(2) . . ?
C33 C32 C35 109.6(2) . . ?
C34 C33 C32 116.1(2) . . ?
C34 C33 H33A 108.3 . . ?
C32 C33 H33A 108.3 . . ?
C34 C33 H33B 108.3 . . ?
C32 C33 H33B 108.3 . . ?
H33A C33 H33B 107.4 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 C32 113.0(2) . . ?
C36 C35 H35A 109.0 . . ?
C32 C35 H35A 109.0 . . ?
C36 C35 H35B 109.0 . . ?
C32 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
O7 C36 C35 123.4(2) . . ?
O7 C36 C37 118.4(2) . . ?
C35 C36 C37 118.2(2) . . ?
N4 C37 C36 117.5(2) . . ?
N4 C37 C39 123.9(2) . . ?
C36 C37 C39 118.6(2) . . ?
O8 C38 H38A 109.5 . . ?
O8 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O8 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O9 C39 O10 125.7(3) . . ?
O9 C39 C37 123.6(3) . . ?
O10 C39 C37 110.7(2) . . ?
O10 C40 H40A 109.5 . . ?
O10 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O10 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C9 N1 C1 127.0(2) . . ?
C9 N1 C8 125.2(3) . . ?
C1 N1 C8 107.7(2) . . ?
C17 N2 O3 111.5(2) . . ?
C29 N3 C21 126.5(2) . . ?
C29 N3 C28 125.1(2) . . ?
C21 N3 C28 108.4(2) . . ?
C37 N4 O8 112.3(2) . . ?
N2 O3 C18 109.6(2) . . ?
C19 O5 C20 116.3(3) . . ?
N4 O8 C38 108.9(2) . . ?
C39 O10 C40 116.7(3) . . ?

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
N1 C1 C2 C3 179.3(3) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C4 C5 C6 C7 -178.1(3) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
N1 C1 C6 C5 -179.7(2) . . . . ?
C2 C1 C6 C7 178.6(3) . . . . ?
N1 C1 C6 C7 -0.9(3) . . . . ?
C5 C6 C7 C8 179.6(3) . . . . ?
C1 C6 C7 C8 1.0(3) . . . . ?
C6 C7 C8 N1 -0.7(3) . . . . ?
C6 C7 C8 C12 178.6(3) . . . . ?
O1 C9 C10 C11 -155.0(3) . . . . ?
N1 C9 C10 C11 26.1(4) . . . . ?
C9 C10 C11 C12 -52.7(4) . . . . ?
C7 C8 C12 C11 155.1(3) . . . . ?
N1 C8 C12 C11 -25.6(3) . . . . ?
C7 C8 C12 C15 -85.3(3) . . . . ?
N1 C8 C12 C15 93.9(3) . . . . ?
C7 C8 C12 C13 36.4(4) . . . . ?
N1 C8 C12 C13 -144.4(2) . . . . ?
C10 C11 C12 C8 50.4(3) . . . . ?
C10 C11 C12 C15 -70.5(3) . . . . ?
C10 C11 C12 C13 167.6(3) . . . . ?
C8 C12 C13 C14 168.2(3) . . . . ?
C11 C12 C13 C14 50.0(4) . . . . ?
C15 C12 C13 C14 -70.3(4) . . . . ?
C8 C12 C15 C16 36.9(3) . . . . ?
C11 C12 C15 C16 156.6(2) . . . . ?
C13 C12 C15 C16 -82.4(3) . . . . ?
C12 C15 C16 O2 86.0(3) . . . . ?
C12 C15 C16 C17 -93.5(3) . . . . ?
O2 C16 C17 N2 -176.4(3) . . . . ?
C15 C16 C17 N2 3.2(4) . . . . ?
O2 C16 C17 C19 2.2(4) . . . . ?
C15 C16 C17 C19 -178.2(2) . . . . ?
N2 C17 C19 O4 83.5(4) . . . . ?
C16 C17 C19 O4 -95.0(4) . . . . ?
N2 C17 C19 O5 -95.8(3) . . . . ?
C16 C17 C19 O5 85.7(3) . . . . ?
C26 C21 C22 C23 0.4(4) . . . . ?
N3 C21 C22 C23 177.7(3) . . . . ?
C21 C22 C23 C24 0.3(5) . . . . ?
C22 C23 C24 C25 -0.5(6) . . . . ?
C23 C24 C25 C26 0.1(5) . . . . ?
C22 C21 C26 C25 -0.7(4) . . . . ?
N3 C21 C26 C25 -178.6(2) . . . . ?
C22 C21 C26 C27 178.5(3) . . . . ?
N3 C21 C26 C27 0.6(3) . . . . ?
C24 C25 C26 C21 0.5(5) . . . . ?
C24 C25 C26 C27 -178.5(3) . . . . ?
C21 C26 C27 C28 -0.6(3) . . . . ?
C25 C26 C27 C28 178.4(3) . . . . ?
C26 C27 C28 N3 0.4(3) . . . . ?
C26 C27 C28 C32 -176.5(2) . . . . ?
O6 C29 C30 C31 154.9(3) . . . . ?
N3 C29 C30 C31 -26.0(3) . . . . ?
C29 C30 C31 C32 52.3(3) . . . . ?
C27 C28 C32 C31 -156.1(3) . . . . ?
N3 C28 C32 C31 27.3(3) . . . . ?
C27 C28 C32 C33 -36.9(4) . . . . ?
N3 C28 C32 C33 146.5(2) . . . . ?
C27 C28 C32 C35 83.5(3) . . . . ?
N3 C28 C32 C35 -93.1(3) . . . . ?
C30 C31 C32 C28 -50.3(3) . . . . ?
C30 C31 C32 C33 -168.6(2) . . . . ?
C30 C31 C32 C35 70.7(3) . . . . ?
C28 C32 C33 C34 -171.3(2) . . . . ?
C31 C32 C33 C34 -53.2(3) . . . . ?
C35 C32 C33 C34 67.7(3) . . . . ?
C28 C32 C35 C36 -34.4(3) . . . . ?
C31 C32 C35 C36 -153.7(2) . . . . ?
C33 C32 C35 C36 85.4(3) . . . . ?
C32 C35 C36 O7 -85.6(3) . . . . ?
C32 C35 C36 C37 92.2(3) . . . . ?
O7 C36 C37 N4 -179.1(2) . . . . ?
C35 C36 C37 N4 2.9(3) . . . . ?
O7 C36 C37 C39 1.3(4) . . . . ?
C35 C36 C37 C39 -176.6(2) . . . . ?
N4 C37 C39 O9 97.9(4) . . . . ?
C36 C37 C39 O9 -82.5(4) . . . . ?
N4 C37 C39 O10 -81.9(3) . . . . ?
C36 C37 C39 O10 97.6(3) . . . . ?
O1 C9 N1 C1 0.8(4) . . . . ?
C10 C9 N1 C1 179.7(3) . . . . ?
O1 C9 N1 C8 -178.8(3) . . . . ?
C10 C9 N1 C8 0.0(4) . . . . ?
C2 C1 N1 C9 1.5(5) . . . . ?
C6 C1 N1 C9 -179.2(2) . . . . ?
C2 C1 N1 C8 -178.9(3) . . . . ?
C6 C1 N1 C8 0.5(3) . . . . ?
C7 C8 N1 C9 179.8(2) . . . . ?
C12 C8 N1 C9 0.4(4) . . . . ?
C7 C8 N1 C1 0.1(3) . . . . ?
C12 C8 N1 C1 -179.3(2) . . . . ?
C16 C17 N2 O3 179.9(2) . . . . ?
C19 C17 N2 O3 1.4(4) . . . . ?
O6 C29 N3 C21 0.2(4) . . . . ?
C30 C29 N3 C21 -178.9(2) . . . . ?
O6 C29 N3 C28 -179.7(2) . . . . ?
C30 C29 N3 C28 1.2(4) . . . . ?
C26 C21 N3 C29 179.7(2) . . . . ?
C22 C21 N3 C29 2.1(4) . . . . ?
C26 C21 N3 C28 -0.4(3) . . . . ?
C22 C21 N3 C28 -178.0(3) . . . . ?
C27 C28 N3 C29 179.9(2) . . . . ?
C32 C28 N3 C29 -2.8(4) . . . . ?
C27 C28 N3 C21 0.0(3) . . . . ?
C32 C28 N3 C21 177.3(2) . . . . ?
C36 C37 N4 O8 -178.8(2) . . . . ?
C39 C37 N4 O8 0.7(4) . . . . ?
C17 N2 O3 C18 -176.1(3) . . . . ?
O4 C19 O5 C20 1.5(5) . . . . ?
C17 C19 O5 C20 -179.3(3) . . . . ?
C37 N4 O8 C38 172.1(2) . . . . ?
O9 C39 O10 C40 -1.1(4) . . . . ?
C37 C39 O10 C40 178.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 995250'
#######################################################################
#
#                 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_x147

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 N2 O5'
_chemical_formula_weight         370.40

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   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                   15.2319(11)
_cell_length_b                   7.8737(6)
_cell_length_c                   15.4675(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.2330(10)
_cell_angle_gamma                90.00
_cell_volume                     1855.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    188(2)
_cell_measurement_reflns_used    3203
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      25.49

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9699
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      188(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            11430
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.34
_diffrn_reflns_theta_max         26.04
_reflns_number_total             3656
_reflns_number_gt                3037
_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 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)+(0.0614P)²+0.4868P] 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         3656
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
C1 C 0.13344(10) 0.1802(2) 0.33117(9) 0.0226(3) Uani 1 1 d . . .
C2 C 0.18374(10) 0.0961(2) 0.40425(9) 0.0222(3) Uani 1 1 d . . .
H2 H 0.1429 0.0622 0.4516 0.027 Uiso 1 1 calc R . .
C3 C 0.22058(10) -0.0603(2) 0.35967(10) 0.0228(3) Uani 1 1 d . . .
C4 C 0.25883(11) -0.2052(2) 0.39367(11) 0.0301(4) Uani 1 1 d . . .
H4 H 0.2645 -0.2190 0.4545 0.036 Uiso 1 1 calc R . .
C5 C 0.28882(12) -0.3304(2) 0.33780(12) 0.0348(4) Uani 1 1 d . . .
H5 H 0.3151 -0.4304 0.3606 0.042 Uiso 1 1 calc R . .
C6 C 0.28074(11) -0.3104(2) 0.24897(12) 0.0331(4) Uani 1 1 d . . .
H6 H 0.3019 -0.3970 0.2117 0.040 Uiso 1 1 calc R . .
C7 C 0.24235(11) -0.1663(2) 0.21354(10) 0.0284(4) Uani 1 1 d . . .
H7 H 0.2375 -0.1521 0.1527 0.034 Uiso 1 1 calc R . .
C8 C 0.21127(10) -0.0438(2) 0.27011(10) 0.0222(3) Uani 1 1 d . . .
C9 C 0.14533(10) 0.1744(2) 0.17214(10) 0.0267(4) Uani 1 1 d . . .
C10 C 0.09562(12) 0.3392(2) 0.17545(11) 0.0349(4) Uani 1 1 d . . .
H10A H 0.0647 0.3557 0.1197 0.042 Uiso 1 1 calc R . .
H10B H 0.1381 0.4334 0.1823 0.042 Uiso 1 1 calc R . .
C11 C 0.02885(12) 0.3489(2) 0.24826(11) 0.0335(4) Uani 1 1 d . . .
H11A H 0.0075 0.4671 0.2537 0.040 Uiso 1 1 calc R . .
H11B H -0.0221 0.2757 0.2341 0.040 Uiso 1 1 calc R . .
C12 C 0.06842(11) 0.2925(2) 0.33330(10) 0.0268(4) Uani 1 1 d . . .
C13 C 0.02905(11) 0.3547(2) 0.41672(11) 0.0319(4) Uani 1 1 d . . .
H13A H 0.0091 0.4735 0.4091 0.038 Uiso 1 1 calc R . .
H13B H 0.0747 0.3537 0.4625 0.038 Uiso 1 1 calc R . .
C14 C -0.04824(13) 0.2457(3) 0.44540(13) 0.0427(5) Uani 1 1 d . . .
H14A H -0.0923 0.2415 0.3991 0.064 Uiso 1 1 calc R . .
H14B H -0.0745 0.2951 0.4974 0.064 Uiso 1 1 calc R . .
H14C H -0.0277 0.1304 0.4582 0.064 Uiso 1 1 calc R . .
C15 C 0.25501(10) 0.2175(2) 0.43905(9) 0.0228(3) Uani 1 1 d . . .
H15A H 0.3023 0.2269 0.3956 0.027 Uiso 1 1 calc R . .
H15B H 0.2290 0.3318 0.4466 0.027 Uiso 1 1 calc R . .
C16 C 0.29429(10) 0.1613(2) 0.52350(10) 0.0240(4) Uani 1 1 d . . .
C17 C 0.35742(10) 0.2771(2) 0.56845(10) 0.0236(3) Uani 1 1 d . . .
C18 C 0.39846(11) 0.2123(2) 0.65123(10) 0.0263(4) Uani 1 1 d . . .
C19 C 0.51749(14) 0.0567(3) 0.70848(13) 0.0471(5) Uani 1 1 d . . .
H19A H 0.5388 0.1492 0.7454 0.071 Uiso 1 1 calc R . .
H19B H 0.5673 -0.0117 0.6888 0.071 Uiso 1 1 calc R . .
H19C H 0.4771 -0.0151 0.7414 0.071 Uiso 1 1 calc R . .
C20 C 0.43723(13) 0.6861(2) 0.55731(12) 0.0359(4) Uani 1 1 d . . .
H20A H 0.4430 0.6868 0.4942 0.054 Uiso 1 1 calc R . .
H20B H 0.4885 0.7413 0.5835 0.054 Uiso 1 1 calc R . .
H20C H 0.3839 0.7477 0.5737 0.054 Uiso 1 1 calc R . .
N1 N 0.16411(8) 0.10685(17) 0.25161(8) 0.0228(3) Uani 1 1 d . . .
N2 N 0.37111(9) 0.42537(18) 0.53752(8) 0.0261(3) Uani 1 1 d . . .
O1 O 0.16907(8) 0.10767(17) 0.10465(7) 0.0346(3) Uani 1 1 d . . .
O2 O 0.27761(8) 0.02626(15) 0.55818(7) 0.0321(3) Uani 1 1 d . . .
O3 O 0.36743(9) 0.23297(17) 0.72127(8) 0.0394(3) Uani 1 1 d . . .
O4 O 0.47177(8) 0.12733(17) 0.63399(8) 0.0369(3) Uani 1 1 d . . .
O5 O 0.43169(8) 0.51406(15) 0.58731(7) 0.0314(3) Uani 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
C1 C12 1.328(2) . ?
C1 N1 1.4391(19) . ?
C1 C2 1.515(2) . ?
C2 C3 1.520(2) . ?
C2 C15 1.542(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.384(2) . ?
C3 C8 1.398(2) . ?
C4 C5 1.389(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(2) . ?
C7 H7 0.9500 . ?
C8 N1 1.415(2) . ?
C9 O1 1.225(2) . ?
C9 N1 1.368(2) . ?
C9 C10 1.503(2) . ?
C10 C11 1.522(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.511(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.507(2) . ?
C13 C14 1.524(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.501(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O2 1.2180(19) . ?
C16 C17 1.495(2) . ?
C17 N2 1.279(2) . ?
C17 C18 1.511(2) . ?
C18 O3 1.195(2) . ?
C18 O4 1.330(2) . ?
C19 O4 1.454(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 O5 1.434(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N2 O5 1.3880(17) . ?

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
C12 C1 N1 122.22(14) . . ?
C12 C1 C2 130.33(14) . . ?
N1 C1 C2 107.30(13) . . ?
C1 C2 C3 101.67(12) . . ?
C1 C2 C15 110.03(13) . . ?
C3 C2 C15 113.57(13) . . ?
C1 C2 H2 110.4 . . ?
C3 C2 H2 110.4 . . ?
C15 C2 H2 110.4 . . ?
C4 C3 C8 119.60(15) . . ?
C4 C3 C2 130.63(14) . . ?
C8 C3 C2 109.77(13) . . ?
C3 C4 C5 119.17(15) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.51(16) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 121.25(16) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 117.62(15) . . ?
C8 C7 H7 121.2 . . ?
C6 C7 H7 121.2 . . ?
C7 C8 C3 121.82(15) . . ?
C7 C8 N1 129.01(14) . . ?
C3 C8 N1 109.12(13) . . ?
O1 C9 N1 122.51(16) . . ?
O1 C9 C10 123.37(15) . . ?
N1 C9 C10 114.10(14) . . ?
C9 C10 C11 113.99(15) . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 111.34(14) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C1 C12 C13 122.48(15) . . ?
C1 C12 C11 117.94(15) . . ?
C13 C12 C11 119.42(15) . . ?
C12 C13 C14 112.12(15) . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
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 . . ?
C16 C15 C2 113.49(13) . . ?
C16 C15 H15A 108.9 . . ?
C2 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C2 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
O2 C16 C17 117.56(14) . . ?
O2 C16 C15 123.87(15) . . ?
C17 C16 C15 118.57(14) . . ?
N2 C17 C16 119.24(14) . . ?
N2 C17 C18 123.89(14) . . ?
C16 C17 C18 116.82(14) . . ?
O3 C18 O4 125.87(15) . . ?
O3 C18 C17 123.94(16) . . ?
O4 C18 C17 110.17(14) . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 N1 C8 127.70(13) . . ?
C9 N1 C1 123.00(14) . . ?
C8 N1 C1 109.25(12) . . ?
C17 N2 O5 111.14(13) . . ?
C18 O4 C19 115.68(15) . . ?
N2 O5 C20 109.60(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
C12 C1 C2 C3 158.91(17) . . . . ?
N1 C1 C2 C3 -16.79(16) . . . . ?
C12 C1 C2 C15 -80.4(2) . . . . ?
N1 C1 C2 C15 103.87(14) . . . . ?
C1 C2 C3 C4 -166.57(17) . . . . ?
C15 C2 C3 C4 75.3(2) . . . . ?
C1 C2 C3 C8 13.26(16) . . . . ?
C15 C2 C3 C8 -104.88(15) . . . . ?
C8 C3 C4 C5 1.2(2) . . . . ?
C2 C3 C4 C5 -178.96(16) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C6 C7 C8 C3 2.2(2) . . . . ?
C6 C7 C8 N1 -174.78(15) . . . . ?
C4 C3 C8 C7 -2.5(2) . . . . ?
C2 C3 C8 C7 177.69(14) . . . . ?
C4 C3 C8 N1 175.08(14) . . . . ?
C2 C3 C8 N1 -4.77(17) . . . . ?
O1 C9 C10 C11 145.51(16) . . . . ?
N1 C9 C10 C11 -36.2(2) . . . . ?
C9 C10 C11 C12 47.9(2) . . . . ?
N1 C1 C12 C13 172.82(15) . . . . ?
C2 C1 C12 C13 -2.3(3) . . . . ?
N1 C1 C12 C11 -2.6(2) . . . . ?
C2 C1 C12 C11 -177.76(16) . . . . ?
C10 C11 C12 C1 -28.6(2) . . . . ?
C10 C11 C12 C13 155.85(16) . . . . ?
C1 C12 C13 C14 -90.5(2) . . . . ?
C11 C12 C13 C14 84.9(2) . . . . ?
C1 C2 C15 C16 167.09(13) . . . . ?
C3 C2 C15 C16 -79.71(16) . . . . ?
C2 C15 C16 O2 6.0(2) . . . . ?
C2 C15 C16 C17 -173.79(13) . . . . ?
O2 C16 C17 N2 -174.46(15) . . . . ?
C15 C16 C17 N2 5.3(2) . . . . ?
O2 C16 C17 C18 2.9(2) . . . . ?
C15 C16 C17 C18 -177.37(14) . . . . ?
N2 C17 C18 O3 87.5(2) . . . . ?
C16 C17 C18 O3 -89.7(2) . . . . ?
N2 C17 C18 O4 -93.95(19) . . . . ?
C16 C17 C18 O4 88.85(17) . . . . ?
O1 C9 N1 C8 -0.2(3) . . . . ?
C10 C9 N1 C8 -178.56(15) . . . . ?
O1 C9 N1 C1 -177.31(15) . . . . ?
C10 C9 N1 C1 4.4(2) . . . . ?
C7 C8 N1 C9 -6.7(3) . . . . ?
C3 C8 N1 C9 176.03(15) . . . . ?
C7 C8 N1 C1 170.73(16) . . . . ?
C3 C8 N1 C1 -6.57(17) . . . . ?
C12 C1 N1 C9 16.6(2) . . . . ?
C2 C1 N1 C9 -167.29(14) . . . . ?
C12 C1 N1 C8 -160.96(15) . . . . ?
C2 C1 N1 C8 15.16(16) . . . . ?
C16 C17 N2 O5 -179.70(13) . . . . ?
C18 C17 N2 O5 3.2(2) . . . . ?
O3 C18 O4 C19 -0.9(3) . . . . ?
C17 C18 O4 C19 -179.49(14) . . . . ?
C17 N2 O5 C20 -172.83(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.04
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 995251'
#######################################################################
#
#                 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_x038

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 N2 O5'
_chemical_formula_weight         370.40

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   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                   9.6837(8)
_cell_length_b                   9.5017(8)
_cell_length_c                   20.5631(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.0440(10)
_cell_angle_gamma                90.00
_cell_volume                     1890.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    188(2)
_cell_measurement_reflns_used    2532
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      25.81

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9678
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      188(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  'Bruker APEX 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            11730
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3707
_reflns_number_gt                2900
_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 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)+(0.0554P)²+0.6127P] 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         3707
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
C1 C 0.02826(18) 0.67205(19) 0.16489(9) 0.0270(4) Uani 1 1 d . . .
C2 C -0.0628(2) 0.7795(2) 0.17853(10) 0.0329(5) Uani 1 1 d . . .
H2 H -0.1592 0.7710 0.1691 0.039 Uiso 1 1 calc R . .
C3 C -0.0066(2) 0.9001(2) 0.20666(10) 0.0361(5) Uani 1 1 d . . .
H3 H -0.0659 0.9765 0.2163 0.043 Uiso 1 1 calc R . .
C4 C 0.1345(2) 0.9124(2) 0.22122(10) 0.0354(5) Uani 1 1 d . . .
H4 H 0.1697 0.9973 0.2398 0.042 Uiso 1 1 calc R . .
C5 C 0.2240(2) 0.8031(2) 0.20908(10) 0.0316(4) Uani 1 1 d . . .
H5 H 0.3199 0.8112 0.2200 0.038 Uiso 1 1 calc R . .
C6 C 0.17072(18) 0.68052(19) 0.18046(9) 0.0269(4) Uani 1 1 d . . .
C7 C 0.23161(18) 0.54816(19) 0.16212(9) 0.0257(4) Uani 1 1 d . . .
C8 C 0.13056(18) 0.46564(19) 0.13692(9) 0.0268(4) Uani 1 1 d . . .
C9 C -0.12347(19) 0.4791(2) 0.11888(10) 0.0335(5) Uani 1 1 d . . .
C10 C -0.1210(2) 0.3251(2) 0.10146(11) 0.0406(5) Uani 1 1 d . . .
H10A H -0.1245 0.3164 0.0534 0.049 Uiso 1 1 calc R . .
H10B H -0.2054 0.2802 0.1177 0.049 Uiso 1 1 calc R . .
C11 C 0.00515(19) 0.2440(2) 0.12851(10) 0.0354(5) Uani 1 1 d . . .
H11A H 0.0046 0.1478 0.1100 0.043 Uiso 1 1 calc R . .
H11B H -0.0001 0.2357 0.1764 0.043 Uiso 1 1 calc R . .
C12 C 0.14055(19) 0.3184(2) 0.11190(9) 0.0294(4) Uani 1 1 d . . .
C13 C 0.1637(2) 0.3211(2) 0.03763(10) 0.0377(5) Uani 1 1 d . . .
H13A H 0.0899 0.3790 0.0164 0.045 Uiso 1 1 calc R . .
H13B H 0.2529 0.3684 0.0303 0.045 Uiso 1 1 calc R . .
C14 C 0.1650(3) 0.1783(3) 0.00434(12) 0.0639(8) Uani 1 1 d . . .
H14A H 0.2351 0.1183 0.0258 0.096 Uiso 1 1 calc R . .
H14B H 0.1868 0.1905 -0.0415 0.096 Uiso 1 1 calc R . .
H14C H 0.0740 0.1341 0.0072 0.096 Uiso 1 1 calc R . .
C15 C 0.26564(19) 0.25290(19) 0.14932(10) 0.0317(5) Uani 1 1 d . . .
H15A H 0.2407 0.2361 0.1949 0.038 Uiso 1 1 calc R . .
H15B H 0.2868 0.1606 0.1297 0.038 Uiso 1 1 calc R . .
C16 C 0.3934(2) 0.3437(2) 0.14908(9) 0.0302(4) Uani 1 1 d . . .
C17 C 0.38003(17) 0.50289(19) 0.16848(9) 0.0265(4) Uani 1 1 d . . .
C18 C 0.43947(18) 0.51438(19) 0.23850(10) 0.0286(4) Uani 1 1 d . . .
C19 C 0.4170(3) 0.6856(3) 0.02702(12) 0.0560(7) Uani 1 1 d . . .
H19A H 0.3432 0.7427 0.0450 0.084 Uiso 1 1 calc R . .
H19B H 0.3937 0.6638 -0.0186 0.084 Uiso 1 1 calc R . .
H19C H 0.5041 0.7381 0.0299 0.084 Uiso 1 1 calc R . .
C20 C 0.4029(2) 0.4570(2) 0.34802(10) 0.0450(6) Uani 1 1 d . . .
H20A H 0.4675 0.3784 0.3546 0.067 Uiso 1 1 calc R . .
H20B H 0.3244 0.4448 0.3763 0.067 Uiso 1 1 calc R . .
H20C H 0.4501 0.5456 0.3588 0.067 Uiso 1 1 calc R . .
N1 N 0.00364(15) 0.53735(16) 0.13730(8) 0.0283(4) Uani 1 1 d . . .
N2 N 0.46749(16) 0.59306(17) 0.12954(8) 0.0302(4) Uani 1 1 d . . .
H2A H 0.5573 0.5611 0.1341 0.036 Uiso 1 1 d R . .
O1 O -0.22709(13) 0.55046(16) 0.11673(8) 0.0432(4) Uani 1 1 d . . .
O2 O 0.50616(14) 0.29958(15) 0.13639(8) 0.0421(4) Uani 1 1 d . . .
O3 O 0.43118(15) 0.55978(15) 0.06255(7) 0.0388(4) Uani 1 1 d . . .
O4 O 0.35372(14) 0.46014(15) 0.28063(7) 0.0404(4) Uani 1 1 d . . .
O5 O 0.55105(14) 0.56103(17) 0.25230(7) 0.0477(4) Uani 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
C1 C2 1.385(3) . ?
C1 C6 1.407(3) . ?
C1 N1 1.417(2) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.445(3) . ?
C7 C8 1.343(2) . ?
C7 C17 1.501(2) . ?
C8 N1 1.406(2) . ?
C8 C12 1.495(3) . ?
C9 O1 1.210(2) . ?
C9 N1 1.390(2) . ?
C9 C10 1.507(3) . ?
C10 C11 1.532(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.539(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C15 1.543(2) . ?
C12 C13 1.552(3) . ?
C13 C14 1.520(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.508(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O2 1.207(2) . ?
C16 C17 1.571(3) . ?
C17 N2 1.463(2) . ?
C17 C18 1.535(3) . ?
C18 O5 1.193(2) . ?
C18 O4 1.325(2) . ?
C19 O3 1.405(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 O4 1.450(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N2 O3 1.445(2) . ?
N2 H2A 0.9229 . ?

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
C2 C1 C6 122.56(18) . . ?
C2 C1 N1 130.40(17) . . ?
C6 C1 N1 107.00(15) . . ?
C1 C2 C3 116.79(18) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C2 C3 C4 121.75(18) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 121.03(19) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 118.58(18) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 119.25(17) . . ?
C5 C6 C7 133.49(17) . . ?
C1 C6 C7 107.26(16) . . ?
C8 C7 C6 108.08(16) . . ?
C8 C7 C17 123.24(17) . . ?
C6 C7 C17 128.68(16) . . ?
C7 C8 N1 109.87(16) . . ?
C7 C8 C12 128.59(16) . . ?
N1 C8 C12 121.53(15) . . ?
O1 C9 N1 120.80(19) . . ?
O1 C9 C10 123.72(18) . . ?
N1 C9 C10 115.48(17) . . ?
C9 C10 C11 114.92(16) . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 C12 111.28(17) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C8 C12 C11 106.71(16) . . ?
C8 C12 C15 105.37(14) . . ?
C11 C12 C15 111.35(16) . . ?
C8 C12 C13 109.65(16) . . ?
C11 C12 C13 112.35(15) . . ?
C15 C12 C13 111.06(16) . . ?
C14 C13 C12 115.61(18) . . ?
C14 C13 H13A 108.4 . . ?
C12 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C12 C13 H13B 108.4 . . ?
H13A C13 H13B 107.4 . . ?
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 . . ?
C16 C15 C12 113.41(15) . . ?
C16 C15 H15A 108.9 . . ?
C12 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C12 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
O2 C16 C15 123.42(18) . . ?
O2 C16 C17 118.22(17) . . ?
C15 C16 C17 118.34(16) . . ?
N2 C17 C7 110.83(15) . . ?
N2 C17 C18 105.46(14) . . ?
C7 C17 C18 112.77(15) . . ?
N2 C17 C16 111.73(15) . . ?
C7 C17 C16 109.95(14) . . ?
C18 C17 C16 105.96(14) . . ?
O5 C18 O4 124.92(18) . . ?
O5 C18 C17 123.76(18) . . ?
O4 C18 C17 111.26(15) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 N1 C8 124.86(16) . . ?
C9 N1 C1 127.12(16) . . ?
C8 N1 C1 107.79(14) . . ?
O3 N2 C17 105.52(13) . . ?
O3 N2 H2A 102.8 . . ?
C17 N2 H2A 108.2 . . ?
C19 O3 N2 109.00(15) . . ?
C18 O4 C20 116.15(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O1 0.92 2.13 3.006(2) 157.3 1_655

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 995252'
#######################################################################
#
#                 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_x161

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 N2 O6'
_chemical_formula_weight         386.40

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   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                   9.3854(18)
_cell_length_b                   18.319(3)
_cell_length_c                   11.434(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.579(3)
_cell_angle_gamma                90.00
_cell_volume                     1852.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    187(2)
_cell_measurement_reflns_used    3268
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      25.04

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      187(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  'Bruker APEX 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            10721
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0645
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.04
_reflns_number_total             3268
_reflns_number_gt                2136
_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 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)+(0.0587P)²+0.1275P] 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         3268
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6161(3) 0.16217(14) 0.5280(3) 0.0323(7) Uani 1 1 d . . .
C2 C 0.7334(3) 0.19347(17) 0.6227(3) 0.0481(8) Uani 1 1 d . . .
H2A H 0.8354 0.1877 0.6264 0.058 Uiso 1 1 calc R . .
C3 C 0.6981(4) 0.23300(18) 0.7110(3) 0.0573(9) Uani 1 1 d . . .
H3A H 0.7770 0.2542 0.7777 0.069 Uiso 1 1 calc R . .
C4 C 0.5485(4) 0.24253(17) 0.7044(3) 0.0540(9) Uani 1 1 d . . .
H4A H 0.5265 0.2696 0.7672 0.065 Uiso 1 1 calc R . .
C5 C 0.4320(3) 0.21319(16) 0.6079(3) 0.0424(8) Uani 1 1 d . . .
H5A H 0.3300 0.2211 0.6028 0.051 Uiso 1 1 calc R . .
C6 C 0.4645(3) 0.17191(14) 0.5181(3) 0.0320(7) Uani 1 1 d . . .
C7 C 0.3728(3) 0.12981(14) 0.4127(2) 0.0284(6) Uani 1 1 d . . .
C8 C 0.2025(3) 0.12911(15) 0.3716(2) 0.0320(7) Uani 1 1 d . . .
C9 C 0.1452(3) 0.20887(16) 0.3607(3) 0.0365(7) Uani 1 1 d . . .
C10 C 0.1620(4) 0.32468(17) 0.2742(4) 0.0703(11) Uani 1 1 d . . .
H10A H 0.2023 0.3468 0.2137 0.105 Uiso 1 1 calc R . .
H10B H 0.2098 0.3474 0.3556 0.105 Uiso 1 1 calc R . .
H10C H 0.0524 0.3324 0.2475 0.105 Uiso 1 1 calc R . .
C11 C -0.0611(4) 0.14360(19) 0.0784(3) 0.0557(9) Uani 1 1 d . . .
H11A H -0.1668 0.1597 0.0477 0.083 Uiso 1 1 calc R . .
H11B H -0.0475 0.1031 0.0272 0.083 Uiso 1 1 calc R . .
H11C H 0.0049 0.1842 0.0740 0.083 Uiso 1 1 calc R . .
C12 C 0.1438(3) 0.02168(17) 0.2287(3) 0.0392(7) Uani 1 1 d . . .
C13 C 0.3008(3) -0.00956(15) 0.2744(3) 0.0379(7) Uani 1 1 d . . .
H13A H 0.2996 -0.0557 0.2292 0.046 Uiso 1 1 calc R . .
H13B H 0.3249 -0.0222 0.3632 0.046 Uiso 1 1 calc R . .
C14 C 0.4315(3) 0.03806(15) 0.2625(2) 0.0325(7) Uani 1 1 d . . .
C15 C 0.3918(3) 0.07380(16) 0.1333(3) 0.0403(7) Uani 1 1 d . . .
H15A H 0.3194 0.1140 0.1276 0.048 Uiso 1 1 calc R . .
H15B H 0.4849 0.0955 0.1255 0.048 Uiso 1 1 calc R . .
C16 C 0.3236(4) 0.02168(19) 0.0247(3) 0.0587(10) Uani 1 1 d . . .
H16A H 0.3016 0.0484 -0.0536 0.088 Uiso 1 1 calc R . .
H16B H 0.2298 0.0009 0.0301 0.088 Uiso 1 1 calc R . .
H16C H 0.3955 -0.0177 0.0280 0.088 Uiso 1 1 calc R . .
C17 C 0.5720(3) -0.01181(16) 0.2905(3) 0.0417(8) Uani 1 1 d . . .
H17A H 0.5821 -0.0411 0.3656 0.050 Uiso 1 1 calc R . .
H17B H 0.5571 -0.0460 0.2204 0.050 Uiso 1 1 calc R . .
C18 C 0.7180(3) 0.03126(17) 0.3111(3) 0.0457(8) Uani 1 1 d . . .
H18A H 0.8043 -0.0031 0.3322 0.055 Uiso 1 1 calc R . .
H18B H 0.7125 0.0563 0.2329 0.055 Uiso 1 1 calc R . .
C19 C 0.7460(3) 0.08666(16) 0.4122(3) 0.0388(7) Uani 1 1 d . . .
C20 C 0.4669(3) 0.09438(14) 0.3639(2) 0.0286(6) Uani 1 1 d . . .
N1 N 0.6176(2) 0.11352(12) 0.4321(2) 0.0327(6) Uani 1 1 d . . .
N2 N 0.1307(2) 0.09682(13) 0.2481(2) 0.0353(6) Uani 1 1 d . . .
O1 O 0.8708(2) 0.10806(12) 0.4744(2) 0.0589(7) Uani 1 1 d . . .
O2 O 0.1939(2) 0.24709(11) 0.2828(2) 0.0475(6) Uani 1 1 d . . .
O3 O 0.0736(2) 0.23256(12) 0.4208(2) 0.0576(6) Uani 1 1 d . . .
O4 O -0.02298(19) 0.11980(11) 0.20501(17) 0.0419(5) Uani 1 1 d . . .
O5 O 0.0359(2) -0.01485(12) 0.1707(2) 0.0613(7) Uani 1 1 d . . .
O6 O 0.1616(2) 0.09264(11) 0.46313(17) 0.0410(5) Uani 1 1 d . . .
H6A H 0.0712 0.1023 0.4547 0.061 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
C1 C2 1.384(4) . ?
C1 C6 1.401(3) . ?
C1 N1 1.417(3) . ?
C2 C3 1.370(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.392(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.376(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.389(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.447(4) . ?
C7 C20 1.357(3) . ?
C7 C8 1.507(4) . ?
C8 O6 1.399(3) . ?
C8 N2 1.469(3) . ?
C8 C9 1.548(4) . ?
C9 O3 1.191(3) . ?
C9 O2 1.329(3) . ?
C10 O2 1.449(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O4 1.437(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O5 1.209(3) . ?
C12 N2 1.406(4) . ?
C12 C13 1.502(4) . ?
C13 C14 1.548(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C20 1.504(4) . ?
C14 C15 1.543(4) . ?
C14 C17 1.547(4) . ?
C15 C16 1.527(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.530(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.494(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O1 1.215(3) . ?
C19 N1 1.389(3) . ?
C20 N1 1.412(3) . ?
N2 O4 1.423(3) . ?
O6 H6A 0.8400 . ?

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
C2 C1 C6 122.0(3) . . ?
C2 C1 N1 130.9(3) . . ?
C6 C1 N1 107.0(2) . . ?
C3 C2 C1 118.1(3) . . ?
C3 C2 H2A 121.0 . . ?
C1 C2 H2A 121.0 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 H5A 120.2 . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 C7 133.6(2) . . ?
C1 C6 C7 107.7(2) . . ?
C20 C7 C6 108.1(2) . . ?
C20 C7 C8 129.5(2) . . ?
C6 C7 C8 122.5(2) . . ?
O6 C8 N2 112.0(2) . . ?
O6 C8 C7 107.4(2) . . ?
N2 C8 C7 113.6(2) . . ?
O6 C8 C9 109.6(2) . . ?
N2 C8 C9 105.5(2) . . ?
C7 C8 C9 108.7(2) . . ?
O3 C9 O2 125.6(3) . . ?
O3 C9 C8 123.1(3) . . ?
O2 C9 C8 111.2(2) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C12 N2 121.8(3) . . ?
O5 C12 C13 121.6(3) . . ?
N2 C12 C13 116.5(2) . . ?
C12 C13 C14 117.9(2) . . ?
C12 C13 H13A 107.8 . . ?
C14 C13 H13A 107.8 . . ?
C12 C13 H13B 107.8 . . ?
C14 C13 H13B 107.8 . . ?
H13A C13 H13B 107.2 . . ?
C20 C14 C15 111.5(2) . . ?
C20 C14 C17 107.0(2) . . ?
C15 C14 C17 111.3(2) . . ?
C20 C14 C13 107.2(2) . . ?
C15 C14 C13 112.3(2) . . ?
C17 C14 C13 107.1(2) . . ?
C16 C15 C14 114.5(3) . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C14 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C14 112.6(2) . . ?
C18 C17 H17A 109.1 . . ?
C14 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C14 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C17 112.6(2) . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
O1 C19 N1 120.6(3) . . ?
O1 C19 C18 123.9(3) . . ?
N1 C19 C18 115.5(2) . . ?
C7 C20 N1 108.9(2) . . ?
C7 C20 C14 129.7(2) . . ?
N1 C20 C14 121.2(2) . . ?
C19 N1 C20 125.8(2) . . ?
C19 N1 C1 125.7(2) . . ?
C20 N1 C1 108.4(2) . . ?
C12 N2 O4 111.5(2) . . ?
C12 N2 C8 120.6(2) . . ?
O4 N2 C8 107.41(19) . . ?
C9 O2 C10 116.9(2) . . ?
N2 O4 C11 108.7(2) . . ?
C8 O6 H6A 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 995253'
#######################################################################
#
#                 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_x178

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 N2 O6'
_chemical_formula_weight         386.40

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   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                   9.6391(8)
_cell_length_b                   27.150(2)
_cell_length_c                   8.0064(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.845(2)
_cell_angle_gamma                90.00
_cell_volume                     1944.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    187(2)
_cell_measurement_reflns_used    3817
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      26.04

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9692
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      187(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  'Bruker APEX 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            10243
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0692
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         26.04
_reflns_number_total             3817
_reflns_number_gt                2381
_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 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)+(0.0990P)²+2.3392P] 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         3817
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.0860
_refine_ls_wR_factor_ref         0.2420
_refine_ls_wR_factor_gt          0.2117
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3759(5) 0.20090(14) 0.1057(5) 0.0356(9) Uani 1 1 d . . .
C2 C 0.2690(4) 0.16650(14) 0.1094(5) 0.0323(9) Uani 1 1 d . . .
C3 C 0.1177(5) 0.17532(15) 0.0120(5) 0.0394(10) Uani 1 1 d . . .
H3A H 0.0443 0.1522 0.0140 0.047 Uiso 1 1 calc R . .
C4 C 0.0763(5) 0.21821(16) -0.0875(6) 0.0471(11) Uani 1 1 d . . .
H4A H -0.0262 0.2247 -0.1558 0.057 Uiso 1 1 calc R . .
C5 C 0.1846(6) 0.25166(16) -0.0872(6) 0.0491(12) Uani 1 1 d . . .
H5A H 0.1540 0.2812 -0.1548 0.059 Uiso 1 1 calc R . .
C6 C 0.3349(5) 0.24407(16) 0.0067(6) 0.0453(11) Uani 1 1 d . . .
H6A H 0.4074 0.2674 0.0038 0.054 Uiso 1 1 calc R . .
C7 C 0.3449(4) 0.12694(14) 0.2273(5) 0.0321(9) Uani 1 1 d . . .
C8 C 0.4937(4) 0.13689(13) 0.2924(5) 0.0319(9) Uani 1 1 d . . .
C9 C 0.6260(5) 0.11024(14) 0.4271(5) 0.0384(10) Uani 1 1 d . . .
C10 C 0.7665(5) 0.12341(16) 0.3885(7) 0.0487(12) Uani 1 1 d . . .
H10A H 0.8555 0.1089 0.4829 0.058 Uiso 1 1 calc R . .
H10B H 0.7582 0.1090 0.2715 0.058 Uiso 1 1 calc R . .
C11 C 0.7872(5) 0.17913(17) 0.3835(7) 0.0570(13) Uani 1 1 d . . .
H11A H 0.8068 0.1928 0.5047 0.068 Uiso 1 1 calc R . .
H11B H 0.8758 0.1860 0.3529 0.068 Uiso 1 1 calc R . .
C12 C 0.6548(5) 0.20459(16) 0.2507(6) 0.0478(11) Uani 1 1 d . . .
C13 C 0.6389(5) 0.12699(16) 0.6184(6) 0.0479(11) Uani 1 1 d . . .
H13A H 0.6514 0.1632 0.6264 0.058 Uiso 1 1 calc R . .
H13B H 0.5438 0.1192 0.6332 0.058 Uiso 1 1 calc R . .
C14 C 0.7664(6) 0.1038(2) 0.7735(7) 0.0704(16) Uani 1 1 d . . .
H14A H 0.7658 0.1164 0.8879 0.106 Uiso 1 1 calc R . .
H14B H 0.8618 0.1120 0.7629 0.106 Uiso 1 1 calc R . .
H14C H 0.7539 0.0679 0.7697 0.106 Uiso 1 1 calc R . .
C15 C 0.6014(5) 0.05393(14) 0.4124(5) 0.0394(10) Uani 1 1 d . . .
H15A H 0.6947 0.0379 0.4926 0.047 Uiso 1 1 calc R . .
H15B H 0.5227 0.0458 0.4596 0.047 Uiso 1 1 calc R . .
C16 C 0.5583(5) 0.03121(15) 0.2295(6) 0.0391(10) Uani 1 1 d . . .
C17 C 0.2612(4) 0.08540(14) 0.2646(5) 0.0362(9) Uani 1 1 d . . .
C18 C 0.1286(6) 0.01664(16) -0.1320(6) 0.0494(12) Uani 1 1 d . . .
H18A H 0.1432 0.0201 -0.2462 0.074 Uiso 1 1 calc R . .
H18B H 0.0222 0.0203 -0.1532 0.074 Uiso 1 1 calc R . .
H18C H 0.1630 -0.0160 -0.0808 0.074 Uiso 1 1 calc R . .
C19 C 0.2263(5) 0.08461(15) 0.4270(5) 0.0374(10) Uani 1 1 d . . .
C20 C 0.2379(6) 0.13017(19) 0.6820(6) 0.0577(13) Uani 1 1 d . . .
H20A H 0.2689 0.1628 0.7350 0.087 Uiso 1 1 calc R . .
H20B H 0.2963 0.1048 0.7659 0.087 Uiso 1 1 calc R . .
H20C H 0.1314 0.1254 0.6580 0.087 Uiso 1 1 calc R . .
N1 N 0.5160(4) 0.18217(11) 0.2184(4) 0.0361(8) Uani 1 1 d . . .
N2 N 0.1946(4) 0.04970(13) 0.1521(5) 0.0449(9) Uani 1 1 d . . .
O1 O 0.6631(4) 0.24260(12) 0.1766(5) 0.0684(11) Uani 1 1 d . . .
O2 O 0.5693(4) 0.05213(10) 0.0999(4) 0.0462(8) Uani 1 1 d . . .
O3 O 0.5088(4) -0.01394(10) 0.2256(4) 0.0501(8) Uani 1 1 d . . .
H3 H 0.4864 -0.0256 0.1216 0.075 Uiso 1 1 calc R . .
O4 O 0.2131(4) 0.05415(11) -0.0080(4) 0.0499(8) Uani 1 1 d . . .
O5 O 0.1695(5) 0.04858(14) 0.4733(5) 0.0746(11) Uani 1 1 d . . .
O6 O 0.2631(4) 0.12650(11) 0.5156(4) 0.0513(9) Uani 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
C1 C6 1.388(6) . ?
C1 C2 1.399(5) . ?
C1 N1 1.411(5) . ?
C2 C3 1.395(6) . ?
C2 C7 1.437(5) . ?
C3 C4 1.383(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.383(7) . ?
C4 H4A 0.9500 . ?
C5 C6 1.377(6) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.358(5) . ?
C7 C17 1.480(5) . ?
C8 N1 1.416(5) . ?
C8 C9 1.513(6) . ?
C9 C10 1.540(6) . ?
C9 C15 1.545(5) . ?
C9 C13 1.558(6) . ?
C10 C11 1.528(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.492(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O1 1.208(5) . ?
C12 N1 1.404(5) . ?
C13 C14 1.521(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.498(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O2 1.222(5) . ?
C16 O3 1.311(5) . ?
C17 N2 1.317(5) . ?
C17 C19 1.460(6) . ?
C18 O4 1.444(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O5 1.243(5) . ?
C19 O6 1.317(5) . ?
C20 O6 1.444(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N2 O4 1.364(4) . ?
O3 H3 0.8400 . ?

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 121.4(4) . . ?
C6 C1 N1 132.2(4) . . ?
C2 C1 N1 106.4(3) . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 C7 131.8(4) . . ?
C1 C2 C7 108.3(3) . . ?
C4 C3 C2 119.0(4) . . ?
C4 C3 H3A 120.5 . . ?
C2 C3 H3A 120.5 . . ?
C3 C4 C5 119.7(4) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C6 C5 C4 122.9(4) . . ?
C6 C5 H5A 118.6 . . ?
C4 C5 H5A 118.6 . . ?
C5 C6 C1 117.2(4) . . ?
C5 C6 H6A 121.4 . . ?
C1 C6 H6A 121.4 . . ?
C8 C7 C2 108.1(3) . . ?
C8 C7 C17 130.6(4) . . ?
C2 C7 C17 121.3(4) . . ?
C7 C8 N1 108.4(3) . . ?
C7 C8 C9 131.9(3) . . ?
N1 C8 C9 119.6(3) . . ?
C8 C9 C10 108.5(3) . . ?
C8 C9 C15 110.7(3) . . ?
C10 C9 C15 109.6(3) . . ?
C8 C9 C13 107.4(3) . . ?
C10 C9 C13 112.1(4) . . ?
C15 C9 C13 108.5(3) . . ?
C11 C10 C9 111.6(4) . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 113.1(4) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
O1 C12 N1 120.8(4) . . ?
O1 C12 C11 123.4(4) . . ?
N1 C12 C11 115.8(4) . . ?
C14 C13 C9 115.2(4) . . ?
C14 C13 H13A 108.5 . . ?
C9 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C9 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
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 . . ?
C16 C15 C9 117.4(3) . . ?
C16 C15 H15A 107.9 . . ?
C9 C15 H15A 107.9 . . ?
C16 C15 H15B 107.9 . . ?
C9 C15 H15B 107.9 . . ?
H15A C15 H15B 107.2 . . ?
O2 C16 O3 124.0(4) . . ?
O2 C16 C15 123.9(4) . . ?
O3 C16 C15 112.0(4) . . ?
N2 C17 C19 112.6(4) . . ?
N2 C17 C7 125.9(4) . . ?
C19 C17 C7 121.0(4) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 O6 125.4(4) . . ?
O5 C19 C17 123.4(4) . . ?
O6 C19 C17 111.2(3) . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C12 N1 C1 125.6(3) . . ?
C12 N1 C8 125.6(4) . . ?
C1 N1 C8 108.8(3) . . ?
C17 N2 O4 112.1(3) . . ?
C16 O3 H3 109.5 . . ?
N2 O4 C18 110.2(3) . . ?
C19 O6 C20 116.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.04
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.251
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 995254'
#######################################################################
#
#                 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_x183

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 N2 O6'
_chemical_formula_weight         386.40

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   P2(1)/c

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

_cell_length_a                   11.626(5)
_cell_length_b                   10.168(4)
_cell_length_c                   15.862(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.357(8)
_cell_angle_gamma                90.00
_cell_volume                     1859.6(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1809
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      23.56

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9678
_exptl_absorpt_correction_T_max  0.9797
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX CCD'
_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            9095
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         25.40
_reflns_number_total             3393
_reflns_number_gt                2396
_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 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)+(0.0765P)²+0.1683P] 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         3393
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1292
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.005
_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 0.80707(18) 1.33210(17) 0.35736(12) 0.0620(6) Uani 1 1 d . . .
O2 O 0.59155(14) 1.07667(18) 0.07561(11) 0.0544(5) Uani 1 1 d . . .
O3 O 0.63431(16) 0.9458(2) -0.02730(13) 0.0646(6) Uani 1 1 d . . .
H3 H 0.5635 0.9396 -0.0365 0.097 Uiso 1 1 calc R . .
O4 O 0.83478(14) 0.64205(15) 0.12650(11) 0.0461(5) Uani 1 1 d . . .
O5 O 0.56635(17) 0.75521(19) 0.15783(14) 0.0689(6) Uani 1 1 d . . .
O6 O 0.66894(14) 0.60633(16) 0.24052(11) 0.0485(5) Uani 1 1 d . . .
N1 N 0.77498(16) 1.13741(17) 0.28779(12) 0.0338(5) Uani 1 1 d . . .
N2 N 0.85478(17) 0.76254(17) 0.16905(12) 0.0364(5) Uani 1 1 d . . .
C1 C 0.73067(19) 1.0683(2) 0.35383(15) 0.0352(6) Uani 1 1 d . . .
C2 C 0.72311(18) 0.9359(2) 0.33064(14) 0.0318(5) Uani 1 1 d . . .
C3 C 0.6797(2) 0.8451(2) 0.38444(15) 0.0404(6) Uani 1 1 d . . .
H3A H 0.6758 0.7561 0.3707 0.048 Uiso 1 1 calc R . .
C4 C 0.6427(2) 0.8900(3) 0.45823(16) 0.0483(7) Uani 1 1 d . . .
H4 H 0.6130 0.8308 0.4946 0.058 Uiso 1 1 calc R . .
C5 C 0.6492(2) 1.0223(3) 0.47912(16) 0.0514(7) Uani 1 1 d . . .
H5 H 0.6231 1.0499 0.5292 0.062 Uiso 1 1 calc R . .
C6 C 0.6932(2) 1.1144(2) 0.42789(16) 0.0451(7) Uani 1 1 d . . .
H6 H 0.6975 1.2031 0.4424 0.054 Uiso 1 1 calc R . .
C7 C 0.76419(18) 0.9244(2) 0.24843(14) 0.0303(5) Uani 1 1 d . . .
C8 C 0.79310(17) 1.0467(2) 0.22300(14) 0.0296(5) Uani 1 1 d . . .
C9 C 0.84011(19) 1.0992(2) 0.14460(14) 0.0317(5) Uani 1 1 d . . .
C10 C 0.8092(2) 1.2468(2) 0.13592(15) 0.0383(6) Uani 1 1 d . . .
H10A H 0.8433 1.2833 0.0883 0.046 Uiso 1 1 calc R . .
H10B H 0.7257 1.2561 0.1238 0.046 Uiso 1 1 calc R . .
C11 C 0.8518(2) 1.3236(2) 0.21524(16) 0.0421(6) Uani 1 1 d . . .
H11A H 0.9359 1.3237 0.2231 0.051 Uiso 1 1 calc R . .
H11B H 0.8261 1.4141 0.2077 0.051 Uiso 1 1 calc R . .
C12 C 0.8100(2) 1.2695(2) 0.29304(17) 0.0410(6) Uani 1 1 d . . .
C13 C 0.97376(19) 1.0784(2) 0.15915(15) 0.0381(6) Uani 1 1 d . . .
H13A H 1.0024 1.1088 0.2159 0.046 Uiso 1 1 calc R . .
H13B H 0.9890 0.9847 0.1573 0.046 Uiso 1 1 calc R . .
C14 C 1.0433(2) 1.1463(3) 0.09675(18) 0.0563(8) Uani 1 1 d . . .
H14A H 1.0091 1.1276 0.0397 0.084 Uiso 1 1 calc R . .
H14B H 1.1217 1.1145 0.1050 0.084 Uiso 1 1 calc R . .
H14C H 1.0430 1.2395 0.1062 0.084 Uiso 1 1 calc R . .
C15 C 0.79126(19) 1.0277(2) 0.06222(14) 0.0342(5) Uani 1 1 d . . .
H15A H 0.8232 1.0701 0.0156 0.041 Uiso 1 1 calc R . .
H15B H 0.8208 0.9384 0.0658 0.041 Uiso 1 1 calc R . .
C16 C 0.6628(2) 1.0203(2) 0.03894(14) 0.0354(5) Uani 1 1 d . . .
C17 C 0.76502(19) 0.7977(2) 0.20326(14) 0.0317(5) Uani 1 1 d . . .
C18 C 0.9309(2) 0.6090(3) 0.08379(18) 0.0559(8) Uani 1 1 d . . .
H18A H 0.9615 0.6874 0.0613 0.084 Uiso 1 1 calc R . .
H18B H 0.9063 0.5493 0.0381 0.084 Uiso 1 1 calc R . .
H18C H 0.9898 0.5680 0.1230 0.084 Uiso 1 1 calc R . .
C19 C 0.6553(2) 0.7169(2) 0.19639(16) 0.0396(6) Uani 1 1 d . . .
C20 C 0.5659(3) 0.5259(3) 0.2415(2) 0.0669(9) Uani 1 1 d . . .
H20A H 0.5055 0.5775 0.2612 0.100 Uiso 1 1 calc R . .
H20B H 0.5836 0.4522 0.2787 0.100 Uiso 1 1 calc R . .
H20C H 0.5403 0.4947 0.1850 0.100 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 C12 1.207(3) . ?
O2 C16 1.215(3) . ?
O3 C16 1.303(3) . ?
O3 H3 0.8200 . ?
O4 N2 1.404(2) . ?
O4 C18 1.419(3) . ?
O5 C19 1.198(3) . ?
O6 C19 1.323(3) . ?
O6 C20 1.453(3) . ?
N1 C12 1.403(3) . ?
N1 C1 1.412(3) . ?
N1 C8 1.416(3) . ?
N2 C17 1.287(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.395(3) . ?
C2 C3 1.395(3) . ?
C2 C7 1.450(3) . ?
C3 C4 1.375(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.363(3) . ?
C7 C17 1.475(3) . ?
C8 C9 1.518(3) . ?
C9 C15 1.539(3) . ?
C9 C10 1.545(3) . ?
C9 C13 1.556(3) . ?
C10 C11 1.510(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.488(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 C14 1.522(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.494(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 C19 1.509(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C16 O3 H3 109.5 . . ?
N2 O4 C18 110.13(17) . . ?
C19 O6 C20 116.2(2) . . ?
C12 N1 C1 124.27(19) . . ?
C12 N1 C8 126.67(18) . . ?
C1 N1 C8 108.46(17) . . ?
C17 N2 O4 110.61(18) . . ?
C6 C1 C2 122.3(2) . . ?
C6 C1 N1 130.1(2) . . ?
C2 C1 N1 107.54(19) . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 C7 133.1(2) . . ?
C1 C2 C7 107.32(18) . . ?
C4 C3 C2 118.5(2) . . ?
C4 C3 H3A 120.7 . . ?
C2 C3 H3A 120.7 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 122.1(2) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 116.7(2) . . ?
C5 C6 H6 121.6 . . ?
C1 C6 H6 121.6 . . ?
C8 C7 C2 108.36(18) . . ?
C8 C7 C17 129.5(2) . . ?
C2 C7 C17 122.05(18) . . ?
C7 C8 N1 108.30(18) . . ?
C7 C8 C9 133.74(19) . . ?
N1 C8 C9 117.95(18) . . ?
C8 C9 C15 113.43(18) . . ?
C8 C9 C10 108.08(17) . . ?
C15 C9 C10 109.06(19) . . ?
C8 C9 C13 106.76(18) . . ?
C15 C9 C13 108.35(17) . . ?
C10 C9 C13 111.19(18) . . ?
C11 C10 C9 112.4(2) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 113.13(19) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
O1 C12 N1 121.1(2) . . ?
O1 C12 C11 123.6(2) . . ?
N1 C12 C11 115.3(2) . . ?
C14 C13 C9 116.5(2) . . ?
C14 C13 H13A 108.2 . . ?
C9 C13 H13A 108.2 . . ?
C14 C13 H13B 108.2 . . ?
C9 C13 H13B 108.2 . . ?
H13A C13 H13B 107.3 . . ?
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 . . ?
C16 C15 C9 118.84(18) . . ?
C16 C15 H15A 107.6 . . ?
C9 C15 H15A 107.6 . . ?
C16 C15 H15B 107.6 . . ?
C9 C15 H15B 107.6 . . ?
H15A C15 H15B 107.0 . . ?
O2 C16 O3 122.8(2) . . ?
O2 C16 C15 125.4(2) . . ?
O3 C16 C15 111.80(19) . . ?
N2 C17 C7 120.25(19) . . ?
N2 C17 C19 122.8(2) . . ?
C7 C17 C19 116.91(18) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 O6 125.7(2) . . ?
O5 C19 C17 121.8(2) . . ?
O6 C19 C17 112.4(2) . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 995255'
