# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2003


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

loop_
_publ_author_name
'Alberto Avenoza'
'Jesus H. Busto'
'Noelia Canal'
'Jesus M. Peregrina'

_publ_contact_author_name        'Prof Alberto Avenoza'
_publ_contact_author_address     
;
Quimica
Universidad de La Rioja
Madre de Dios, 51
Logrono
La Rioja
E-26006
SPAIN
;

_publ_contact_author_email       ALBERTO.AVENOZA@DQ.UNIRIOJA.ES

_publ_section_title              
;
Reactivity of 2-acylaminoacrylates with 
ketene diethyl acetal; [2+2] cycloadditions vs. tandem condensations
;

data_shelxl_2
_database_code_CSD               204646

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
AcNH-C4Ser-CH2O-SiPh2tBu
;
_chemical_name_common            AcNH-C4Ser-CH2O-SiPh2tBu
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H31 N1 O3 Si1'
_chemical_formula_weight         397.58

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   15.8810(3)
_cell_length_b                   8.8310(2)
_cell_length_c                   18.6380(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.0891(9)
_cell_angle_gamma                90.00
_cell_volume                     2238.44(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    20035
_cell_measurement_theta_min      1.02
_cell_measurement_theta_max      27.88

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16905
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.28
_diffrn_reflns_theta_max         27.92
_reflns_number_total             5311
_reflns_number_gt                4114
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       KappaCCD
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0658P)^2^+1.0465P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5311
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1440
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Si1 Si 0.78437(3) 0.31104(6) 0.48127(3) 0.03090(14) Uani 1 1 d . . .
O2 O 0.43610(10) 0.48211(14) 0.24228(8) 0.0369(3) Uani 1 1 d . . .
O3 O 0.40443(10) 0.52063(16) 0.37659(9) 0.0423(3) Uani 1 1 d . . .
H3 H 0.4045 0.5684 0.3291 0.051 Uiso 1 1 d R . .
O4 O 0.67391(8) 0.27034(15) 0.46279(8) 0.0337(3) Uani 1 1 d . . .
C5 C 0.45991(13) 0.3506(2) 0.23583(11) 0.0320(4) Uani 1 1 d . . .
N6 N 0.49040(10) 0.24900(17) 0.29721(9) 0.0304(3) Uani 1 1 d . . .
H6 H 0.5074 0.1486 0.2894 0.036 Uiso 1 1 d R . .
C7 C 0.77467(13) 0.3952(2) 0.38464(11) 0.0350(4) Uani 1 1 d . . .
C8 C 0.59349(12) 0.3735(2) 0.43334(11) 0.0311(4) Uani 1 1 d . . .
H8A H 0.5996 0.4654 0.3982 0.037 Uiso 1 1 d R . .
H8B H 0.5879 0.4191 0.4801 0.037 Uiso 1 1 d R . .
C9 C 0.49861(12) 0.28732(19) 0.37669(10) 0.0283(3) Uani 1 1 d . . .
C10 C 0.85092(13) 0.1237(2) 0.51522(12) 0.0390(4) Uani 1 1 d . . .
C11 C 0.84653(13) 0.4512(2) 0.56927(11) 0.0359(4) Uani 1 1 d . . .
C12 C 0.48312(14) 0.1569(2) 0.42431(12) 0.0349(4) Uani 1 1 d . . .
H12A H 0.4498 0.0747 0.3863 0.042 Uiso 1 1 d R . .
H12B H 0.5458 0.1227 0.4691 0.042 Uiso 1 1 d R . .
C13 C 0.40715(12) 0.3630(2) 0.36992(11) 0.0325(4) Uani 1 1 d . . .
H13 H 0.3400 0.3358 0.3125 0.039 Uiso 1 1 d R . .
C14 C 0.42227(14) 0.2678(2) 0.44408(12) 0.0389(4) Uani 1 1 d . . .
H14A H 0.4616 0.3230 0.5000 0.047 Uiso 1 1 d R . .
H14B H 0.3680 0.2187 0.4498 0.047 Uiso 1 1 d R . .
C15 C 0.96155(14) 0.1465(3) 0.55139(14) 0.0492(5) Uani 1 1 d . . .
H15A H 0.9947 0.0506 0.5684 0.059 Uiso 1 1 d R . .
H15B H 0.9873 0.2129 0.5989 0.059 Uiso 1 1 d R . .
H15C H 0.9717 0.1905 0.5094 0.059 Uiso 1 1 d R . .
C16 C 0.45379(17) 0.2996(2) 0.15648(12) 0.0441(5) Uani 1 1 d . . .
H16A H 0.4747 0.1961 0.1619 0.053 Uiso 1 1 d R . .
H16B H 0.4954 0.3624 0.1458 0.053 Uiso 1 1 d R . .
H16C H 0.3870 0.3083 0.1109 0.053 Uiso 1 1 d R . .
C17 C 0.80082(15) 0.5451(2) 0.38216(13) 0.0435(5) Uani 1 1 d . . .
H17 H 0.8224 0.6152 0.4327 0.052 Uiso 1 1 d R . .
C18 C 0.80757(15) 0.4813(3) 0.61990(12) 0.0478(5) Uani 1 1 d . . .
H18 H 0.7458 0.4175 0.6141 0.057 Uiso 1 1 d R . .
C19 C 0.93385(14) 0.5258(3) 0.58896(13) 0.0442(5) Uani 1 1 d . . .
H19 H 0.9634 0.5057 0.5520 0.053 Uiso 1 1 d R . .
C20 C 0.73852(16) 0.3111(3) 0.31055(12) 0.0447(5) Uani 1 1 d . . .
H20 H 0.7260 0.1978 0.3102 0.054 Uiso 1 1 d R . .
C21 C 0.76254(16) 0.5195(3) 0.24060(14) 0.0507(6) Uani 1 1 d . . .
H21 H 0.7612 0.5553 0.1878 0.061 Uiso 1 1 d R . .
C22 C 0.83532(17) 0.0610(3) 0.58436(15) 0.0552(6) Uani 1 1 d . . .
H22A H 0.8682 -0.0346 0.6038 0.066 Uiso 1 1 d R . .
H22B H 0.7663 0.0478 0.5627 0.066 Uiso 1 1 d R . .
H22C H 0.8618 0.1316 0.6301 0.066 Uiso 1 1 d R . .
C23 C 0.81239(16) 0.0077(3) 0.44395(15) 0.0537(6) Uani 1 1 d . . .
H23A H 0.8489 -0.0848 0.4648 0.064 Uiso 1 1 d R . .
H23B H 0.8202 0.0466 0.3996 0.064 Uiso 1 1 d R . .
H23C H 0.7440 -0.0117 0.4229 0.064 Uiso 1 1 d R . .
C24 C 0.79486(16) 0.6069(3) 0.31127(14) 0.0517(5) Uani 1 1 d . . .
H24 H 0.8182 0.7160 0.3112 0.062 Uiso 1 1 d R . .
C25 C 0.97853(16) 0.6288(3) 0.65446(14) 0.0555(6) Uani 1 1 d . . .
H25 H 1.0462 0.6841 0.6700 0.067 Uiso 1 1 d R . .
C26 C 0.73362(17) 0.3720(3) 0.23979(13) 0.0531(6) Uani 1 1 d . . .
H26 H 0.7065 0.3070 0.1824 0.064 Uiso 1 1 d R . .
C27 C 0.85291(18) 0.5834(3) 0.68608(14) 0.0652(7) Uani 1 1 d . . .
H27 H 0.8231 0.6007 0.7226 0.078 Uiso 1 1 d R . .
C28 C 0.93750(18) 0.6588(3) 0.70210(15) 0.0649(7) Uani 1 1 d . . .
H28 H 0.9694 0.7356 0.7490 0.078 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Si1 0.0265(2) 0.0408(3) 0.0277(2) -0.0015(2) 0.01574(19) 0.00313(19)
O2 0.0474(7) 0.0328(7) 0.0344(7) 0.0028(5) 0.0237(6) 0.0045(5)
O3 0.0437(7) 0.0453(8) 0.0459(8) -0.0001(6) 0.0289(7) 0.0061(6)
O4 0.0275(6) 0.0406(7) 0.0349(7) 0.0032(5) 0.0176(5) 0.0064(5)
C5 0.0339(8) 0.0345(9) 0.0294(9) -0.0017(7) 0.0176(7) -0.0008(7)
N6 0.0354(7) 0.0314(7) 0.0277(7) -0.0004(6) 0.0186(6) 0.0010(6)
C7 0.0288(8) 0.0470(11) 0.0314(9) -0.0005(8) 0.0171(7) 0.0022(7)
C8 0.0262(8) 0.0360(9) 0.0320(9) -0.0023(7) 0.0156(7) 0.0042(7)
C9 0.0287(8) 0.0336(9) 0.0263(8) 0.0005(7) 0.0169(7) 0.0009(6)
C10 0.0306(9) 0.0461(11) 0.0403(10) -0.0007(8) 0.0182(8) 0.0070(8)
C11 0.0302(8) 0.0461(11) 0.0291(9) -0.0020(8) 0.0137(7) 0.0063(7)
C12 0.0374(9) 0.0386(10) 0.0337(9) 0.0019(8) 0.0219(8) -0.0006(7)
C13 0.0290(8) 0.0395(10) 0.0328(9) 0.0006(7) 0.0186(7) 0.0020(7)
C14 0.0400(10) 0.0489(11) 0.0382(10) -0.0006(8) 0.0276(9) -0.0020(8)
C15 0.0317(9) 0.0616(14) 0.0503(12) -0.0083(10) 0.0184(9) 0.0106(9)
C16 0.0633(13) 0.0410(11) 0.0341(10) 0.0024(8) 0.0295(10) 0.0062(9)
C17 0.0442(11) 0.0487(12) 0.0342(10) 0.0011(9) 0.0179(9) -0.0006(9)
C18 0.0379(10) 0.0708(15) 0.0336(10) -0.0073(10) 0.0176(8) 0.0102(10)
C19 0.0362(10) 0.0526(12) 0.0383(10) -0.0044(9) 0.0154(8) 0.0001(9)
C20 0.0492(11) 0.0537(12) 0.0341(10) -0.0039(9) 0.0235(9) -0.0037(9)
C21 0.0428(11) 0.0749(16) 0.0382(11) 0.0143(11) 0.0236(9) 0.0059(10)
C22 0.0525(13) 0.0600(14) 0.0558(14) 0.0199(11) 0.0299(11) 0.0176(11)
C23 0.0434(11) 0.0482(12) 0.0613(14) -0.0094(11) 0.0212(11) 0.0066(9)
C24 0.0458(11) 0.0603(14) 0.0450(12) 0.0130(10) 0.0206(10) -0.0023(10)
C25 0.0399(11) 0.0582(14) 0.0456(12) -0.0086(11) 0.0060(10) -0.0012(10)
C26 0.0552(13) 0.0735(16) 0.0342(11) -0.0037(10) 0.0256(10) 0.0023(11)
C27 0.0516(13) 0.096(2) 0.0392(12) -0.0202(12) 0.0176(10) 0.0188(13)
C28 0.0530(14) 0.0717(17) 0.0423(12) -0.0210(12) 0.0049(11) 0.0133(12)

_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
Si1 O4 1.6436(13) . ?
Si1 C11 1.877(2) . ?
Si1 C7 1.8797(19) . ?
Si1 C10 1.888(2) . ?
O2 C5 1.246(2) . ?
O3 C13 1.400(2) . ?
O3 H3 0.9810 . ?
O4 C8 1.428(2) . ?
C5 N6 1.333(2) . ?
C5 C16 1.500(3) . ?
N6 C9 1.458(2) . ?
N6 H6 0.9599 . ?
C7 C17 1.395(3) . ?
C7 C20 1.403(3) . ?
C8 C9 1.524(2) . ?
C8 H8A 1.0780 . ?
C8 H8B 1.0054 . ?
C9 C13 1.544(2) . ?
C9 C12 1.549(2) . ?
C10 C23 1.533(3) . ?
C10 C15 1.536(3) . ?
C10 C22 1.536(3) . ?
C11 C18 1.395(3) . ?
C11 C19 1.402(3) . ?
C12 C14 1.548(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C13 C14 1.527(3) . ?
C13 H13 1.0774 . ?
C14 H14A 1.0205 . ?
C14 H14B 1.0181 . ?
C15 H15A 0.9599 . ?
C15 H15B 0.9598 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9601 . ?
C16 H16B 0.9599 . ?
C16 H16C 0.9600 . ?
C17 C24 1.387(3) . ?
C17 H17 1.0278 . ?
C18 C27 1.391(3) . ?
C18 H18 1.0878 . ?
C19 C25 1.388(3) . ?
C19 H19 1.0300 . ?
C20 C26 1.389(3) . ?
C20 H20 1.0199 . ?
C21 C24 1.377(3) . ?
C21 C26 1.379(4) . ?
C21 H21 1.0234 . ?
C22 H22A 0.9601 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9601 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24 1.0328 . ?
C25 C28 1.371(4) . ?
C25 H25 1.0752 . ?
C26 H26 1.0880 . ?
C27 C28 1.387(4) . ?
C27 H27 1.0214 . ?
C28 H28 1.0118 . ?

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
O4 Si1 C11 110.49(7) . . ?
O4 Si1 C7 109.58(7) . . ?
C11 Si1 C7 108.80(9) . . ?
O4 Si1 C10 103.34(8) . . ?
C11 Si1 C10 109.52(8) . . ?
C7 Si1 C10 114.99(9) . . ?
C13 O3 H3 109.4 . . ?
C8 O4 Si1 125.95(12) . . ?
O2 C5 N6 122.58(16) . . ?
O2 C5 C16 120.43(16) . . ?
N6 C5 C16 116.98(16) . . ?
C5 N6 C9 121.19(15) . . ?
C5 N6 H6 119.8 . . ?
C9 N6 H6 119.0 . . ?
C17 C7 C20 116.55(18) . . ?
C17 C7 Si1 121.90(15) . . ?
C20 C7 Si1 121.53(15) . . ?
O4 C8 C9 108.42(14) . . ?
O4 C8 H8A 111.8 . . ?
C9 C8 H8A 108.8 . . ?
O4 C8 H8B 112.6 . . ?
C9 C8 H8B 107.6 . . ?
H8A C8 H8B 107.5 . . ?
N6 C9 C8 110.95(14) . . ?
N6 C9 C13 115.51(14) . . ?
C8 C9 C13 113.12(14) . . ?
N6 C9 C12 116.88(14) . . ?
C8 C9 C12 111.54(14) . . ?
C13 C9 C12 86.99(13) . . ?
C23 C10 C15 108.79(16) . . ?
C23 C10 C22 108.72(19) . . ?
C15 C10 C22 108.82(17) . . ?
C23 C10 Si1 113.04(14) . . ?
C15 C10 Si1 110.36(15) . . ?
C22 C10 Si1 107.00(14) . . ?
C18 C11 C19 117.22(19) . . ?
C18 C11 Si1 119.98(15) . . ?
C19 C11 Si1 122.77(15) . . ?
C14 C12 C9 88.24(14) . . ?
C14 C12 H12A 118.7 . . ?
C9 C12 H12A 109.3 . . ?
C14 C12 H12B 119.1 . . ?
C9 C12 H12B 109.4 . . ?
H12A C12 H12B 109.5 . . ?
O3 C13 C14 117.66(16) . . ?
O3 C13 C9 119.60(15) . . ?
C14 C13 C9 89.22(13) . . ?
O3 C13 H13 104.4 . . ?
C14 C13 H13 112.9 . . ?
C9 C13 H13 113.0 . . ?
C13 C14 C12 87.61(13) . . ?
C13 C14 H14A 112.9 . . ?
C12 C14 H14A 114.6 . . ?
C13 C14 H14B 125.7 . . ?
C12 C14 H14B 114.9 . . ?
H14A C14 H14B 101.6 . . ?
C10 C15 H15A 109.7 . . ?
C10 C15 H15B 109.4 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.3 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 H16A 109.9 . . ?
C5 C16 H16B 109.3 . . ?
H16A C16 H16B 109.5 . . ?
C5 C16 H16C 109.2 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C24 C17 C7 122.0(2) . . ?
C24 C17 H17 117.6 . . ?
C7 C17 H17 120.3 . . ?
C27 C18 C11 121.1(2) . . ?
C27 C18 H18 116.8 . . ?
C11 C18 H18 121.8 . . ?
C25 C19 C11 121.7(2) . . ?
C25 C19 H19 119.9 . . ?
C11 C19 H19 118.3 . . ?
C26 C20 C7 121.6(2) . . ?
C26 C20 H20 117.3 . . ?
C7 C20 H20 120.3 . . ?
C24 C21 C26 119.8(2) . . ?
C24 C21 H21 124.0 . . ?
C26 C21 H21 116.1 . . ?
C10 C22 H22A 110.0 . . ?
C10 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C10 C22 H22C 108.9 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C23 H23A 109.3 . . ?
C10 C23 H23B 109.6 . . ?
H23A C23 H23B 109.5 . . ?
C10 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 C17 119.9(2) . . ?
C21 C24 H24 118.6 . . ?
C17 C24 H24 121.3 . . ?
C28 C25 C19 119.9(2) . . ?
C28 C25 H25 118.8 . . ?
C19 C25 H25 121.3 . . ?
C21 C26 C20 120.0(2) . . ?
C21 C26 H26 118.0 . . ?
C20 C26 H26 122.0 . . ?
C28 C27 C18 120.2(2) . . ?
C28 C27 H27 121.0 . . ?
C18 C27 H27 118.8 . . ?
C25 C28 C27 119.9(2) . . ?
C25 C28 H28 119.8 . . ?
C27 C28 H28 120.3 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.92
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.047


data_shelxl
_database_code_CSD               204647

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
NOE2 
;
_chemical_name_common            NOE2
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H21 N1 O5'
_chemical_formula_weight         518.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   9.3229(3)
_cell_length_b                   13.8767(5)
_cell_length_c                   22.3925(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2896.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1735
_cell_measurement_theta_min      1.018
_cell_measurement_theta_max      21.036

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3068
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0553
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         21.02
_reflns_number_total             3068
_reflns_number_gt                2550
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       KappaCCD
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+1.0631P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(19)
_refine_ls_number_reflns         3068
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
O1 O 0.6722(3) 0.2546(2) 0.62367(13) 0.0699(8) Uani 1 1 d . . .
O2 O 0.4757(3) 0.2142(2) 0.56495(13) 0.0738(8) Uani 1 1 d . . .
O3 O 0.3251(3) 0.1743(2) 0.69454(14) 0.0712(8) Uani 1 1 d . . .
O4 O 0.1936(3) 0.2178(2) 0.85274(13) 0.0782(9) Uani 1 1 d . . .
N5 N -0.0082(3) 0.3180(2) 0.79138(16) 0.0609(9) Uani 1 1 d . . .
H5 H 0.0891 0.3437 0.7915 0.073 Uiso 1 1 d R . .
O6 O -0.2360(3) 0.3300(2) 0.76090(13) 0.0798(9) Uani 1 1 d . . .
O7 O 0.0941(3) 0.2752(3) 0.94058(14) 0.0852(10) Uani 1 1 d . . .
O8 O 0.2668(3) 0.3877(2) 0.74022(15) 0.0827(9) Uani 1 1 d . . .
C9 C 0.2939(5) 0.2431(3) 0.6551(2) 0.0656(12) Uani 1 1 d . . .
C10 C -0.0527(4) 0.2694(3) 0.84457(19) 0.0624(11) Uani 1 1 d . . .
C11 C 0.5387(4) 0.2824(3) 0.60216(19) 0.0649(11) Uani 1 1 d . . .
C12 C 0.3972(5) 0.3803(3) 0.7466(2) 0.0661(12) Uani 1 1 d . . .
C13 C 0.4182(4) 0.3120(3) 0.64758(18) 0.0584(11) Uani 1 1 d . . .
N14 N 0.4808(3) 0.3417(2) 0.70431(15) 0.0595(9) Uani 1 1 d . . .
H14 H 0.5860 0.3401 0.7032 0.071 Uiso 1 1 d R . .
O15 O 0.1841(3) 0.2466(3) 0.62770(15) 0.0875(10) Uani 1 1 d . . .
C16 C 0.0684(5) 0.2282(3) 0.8867(2) 0.0724(13) Uani 1 1 d . . .
O17 O -0.1277(4) 0.4222(3) 0.88236(16) 0.0987(12) Uani 1 1 d . . .
C18 C -0.1083(5) 0.3467(3) 0.75196(19) 0.0615(11) Uani 1 1 d . . .
C19 C 0.4691(5) 0.4171(4) 0.8016(2) 0.0847(15) Uani 1 1 d . . .
H19A H 0.5707 0.4065 0.7989 0.102 Uiso 1 1 d R . .
H19B H 0.4319 0.3834 0.8357 0.102 Uiso 1 1 d R . .
H19C H 0.4505 0.4848 0.8058 0.102 Uiso 1 1 d R . .
C20 C 0.3882(5) 0.3980(4) 0.6059(2) 0.0804(14) Uani 1 1 d . . .
H20A H 0.3050 0.3851 0.5819 0.096 Uiso 1 1 d R . .
H20B H 0.3709 0.4537 0.6303 0.096 Uiso 1 1 d R . .
C21 C 0.6763(5) 0.1599(3) 0.6521(2) 0.0791(13) Uani 1 1 d . . .
H21A H 0.6387 0.1655 0.6919 0.095 Uiso 1 1 d R . .
H21B H 0.6181 0.1159 0.6296 0.095 Uiso 1 1 d R . .
C22 C -0.0575(5) 0.3984(3) 0.69784(19) 0.0736(13) Uani 1 1 d . . .
H22A H -0.1382 0.4149 0.6733 0.088 Uiso 1 1 d R . .
H22B H 0.0069 0.3580 0.6756 0.088 Uiso 1 1 d R . .
H22C H -0.0085 0.4561 0.7098 0.088 Uiso 1 1 d R . .
O23 O -0.2511(4) 0.2927(3) 0.91084(19) 0.1155(13) Uani 1 1 d . . .
C24 C 0.2126(5) 0.1067(4) 0.7070(3) 0.0969(17) Uani 1 1 d . . .
H24A H 0.2451 0.0604 0.7359 0.116 Uiso 1 1 d R . .
H24B H 0.1863 0.0741 0.6708 0.116 Uiso 1 1 d R . .
H24C H 0.1309 0.1405 0.7226 0.116 Uiso 1 1 d R . .
C25 C -0.1073(5) 0.1643(3) 0.8398(2) 0.0848(15) Uani 1 1 d . . .
H25A H -0.2132 0.1697 0.8337 0.102 Uiso 1 1 d R . .
H25B H -0.0667 0.1335 0.8048 0.102 Uiso 1 1 d R . .
C26 C 0.5358(5) 0.3860(3) 0.5776(2) 0.0830(14) Uani 1 1 d . . .
H26A H 0.6155 0.4204 0.5943 0.100 Uiso 1 1 d R . .
H26B H 0.5445 0.3846 0.5349 0.100 Uiso 1 1 d R . .
C27 C -0.0212(6) 0.1359(3) 0.8941(2) 0.0941(16) Uani 1 1 d . . .
H27A H 0.0407 0.0807 0.8929 0.113 Uiso 1 1 d R . .
H27B H -0.0681 0.1390 0.9322 0.113 Uiso 1 1 d R . .
C28 C 0.5505(6) 0.1960(4) 0.5097(2) 0.1020(18) Uani 1 1 d . . .
H28A H 0.5481 0.2538 0.4862 0.122 Uiso 1 1 d R . .
H28B H 0.6483 0.1789 0.5179 0.122 Uiso 1 1 d R . .
C29 C 0.8244(5) 0.1259(4) 0.6530(3) 0.118(2) Uani 1 1 d . . .
H29A H 0.8273 0.0639 0.6721 0.141 Uiso 1 1 d R . .
H29B H 0.8824 0.1705 0.6751 0.141 Uiso 1 1 d R . .
H29C H 0.8607 0.1204 0.6131 0.141 Uiso 1 1 d R . .
C30 C 0.2995(6) 0.1560(5) 0.8802(3) 0.123(2) Uani 1 1 d . . .
H30A H 0.3191 0.1782 0.9200 0.148 Uiso 1 1 d R . .
H30B H 0.2616 0.0918 0.8818 0.148 Uiso 1 1 d R . .
C31 C -0.1528(6) 0.3328(5) 0.8813(2) 0.0892(16) Uani 1 1 d . A .
C32 C 0.1742(6) 0.3624(4) 0.9365(3) 0.0992(17) Uani 1 1 d . . .
H32A H 0.2746 0.3484 0.9325 0.119 Uiso 1 1 d R . .
H32B H 0.1421 0.3978 0.9022 0.119 Uiso 1 1 d R . .
C33 C 0.4768(7) 0.1189(5) 0.4771(2) 0.117(2) Uani 1 1 d . . .
H33A H 0.5247 0.1067 0.4399 0.140 Uiso 1 1 d R . .
H33B H 0.3798 0.1384 0.4695 0.140 Uiso 1 1 d R . .
H33C H 0.4768 0.0613 0.5008 0.140 Uiso 1 1 d R . .
C34 C 0.4300(6) 0.1535(5) 0.8455(3) 0.139(3) Uani 1 1 d . . .
H34A H 0.4986 0.1111 0.8637 0.167 Uiso 1 1 d R . .
H34B H 0.4684 0.2176 0.8442 0.167 Uiso 1 1 d R . .
H34C H 0.4101 0.1319 0.8056 0.167 Uiso 1 1 d R . .
C36 C 0.1495(7) 0.4199(5) 0.9915(3) 0.133(2) Uani 1 1 d . . .
H36A H 0.2015 0.4794 0.9889 0.160 Uiso 1 1 d R . .
H36B H 0.1823 0.3840 1.0255 0.160 Uiso 1 1 d R . .
H36C H 0.0490 0.4332 0.9957 0.160 Uiso 1 1 d R . .
C38 C -0.2371(14) 0.4690(9) 0.9246(5) 0.115(4) Uani 0.50 1 d P A 1
H38A H -0.2200 0.5372 0.9263 0.172 Uiso 0.50 1 calc PR A 1
H38B H -0.2272 0.4419 0.9638 0.172 Uiso 0.50 1 calc PR A 1
H38C H -0.3323 0.4574 0.9100 0.172 Uiso 0.50 1 calc PR A 1
C37 C -0.3200(13) 0.3721(10) 0.9474(5) 0.118(4) Uani 0.50 1 d P A 2
H37A H -0.3963 0.3456 0.9710 0.176 Uiso 0.50 1 calc PR A 2
H37B H -0.3579 0.4205 0.9211 0.176 Uiso 0.50 1 calc PR A 2
H37C H -0.2495 0.4005 0.9732 0.176 Uiso 0.50 1 calc PR A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0496(16) 0.076(2) 0.084(2) -0.0001(17) 0.0075(14) -0.0062(14)
O2 0.0662(17) 0.094(2) 0.0611(19) -0.0105(17) 0.0056(15) -0.0066(17)
O3 0.0538(17) 0.070(2) 0.090(2) 0.0005(19) 0.0051(16) -0.0108(16)
O4 0.0733(19) 0.091(2) 0.070(2) 0.0075(18) -0.0046(16) 0.0263(17)
N5 0.053(2) 0.067(2) 0.063(2) 0.0093(19) -0.0038(19) 0.0007(17)
O6 0.0431(18) 0.122(3) 0.075(2) 0.0045(19) 0.0011(15) 0.0039(17)
O7 0.098(2) 0.093(3) 0.065(2) 0.006(2) -0.0066(17) 0.015(2)
O8 0.0478(19) 0.102(2) 0.098(2) -0.013(2) 0.0007(17) 0.0026(16)
C9 0.053(3) 0.074(3) 0.071(3) -0.009(3) 0.003(2) -0.001(2)
C10 0.056(2) 0.063(3) 0.068(3) 0.005(2) 0.003(2) 0.006(2)
C11 0.055(3) 0.075(3) 0.065(3) -0.001(3) -0.001(2) -0.012(2)
C12 0.052(3) 0.072(3) 0.074(3) -0.009(3) -0.005(3) -0.006(2)
C13 0.051(2) 0.064(3) 0.060(3) 0.001(2) -0.001(2) 0.001(2)
N14 0.0449(19) 0.066(2) 0.067(2) -0.0096(19) 0.0048(18) -0.0014(17)
O15 0.0504(17) 0.119(3) 0.093(2) -0.007(2) -0.0131(17) -0.0066(17)
C16 0.090(3) 0.069(3) 0.059(3) 0.003(3) 0.001(3) 0.015(3)
O17 0.118(3) 0.088(3) 0.091(3) -0.010(2) -0.005(2) 0.039(2)
C18 0.060(3) 0.066(3) 0.058(3) -0.004(2) -0.001(2) 0.009(2)
C19 0.065(3) 0.098(4) 0.092(4) -0.024(3) 0.007(3) -0.002(3)
C20 0.073(3) 0.083(3) 0.086(3) 0.006(3) -0.005(3) 0.004(2)
C21 0.068(3) 0.077(3) 0.091(3) 0.003(3) -0.004(3) 0.002(2)
C22 0.070(3) 0.081(3) 0.071(3) 0.008(3) -0.002(2) 0.012(2)
O23 0.111(3) 0.138(3) 0.098(3) 0.021(3) 0.043(2) 0.022(3)
C24 0.081(4) 0.076(3) 0.134(5) -0.006(3) 0.023(3) -0.021(3)
C25 0.082(3) 0.078(4) 0.094(4) 0.007(3) 0.006(3) -0.005(3)
C26 0.080(3) 0.083(3) 0.086(3) 0.022(3) 0.003(3) -0.008(3)
C27 0.116(4) 0.073(3) 0.094(4) 0.024(3) 0.002(3) 0.012(3)
C28 0.099(4) 0.138(5) 0.069(3) -0.025(3) 0.020(3) -0.021(4)
C29 0.073(3) 0.096(4) 0.183(6) -0.006(5) -0.006(4) 0.014(3)
C30 0.118(5) 0.142(5) 0.109(4) 0.025(4) -0.008(4) 0.065(4)
C31 0.087(4) 0.113(5) 0.067(3) 0.005(4) -0.009(3) 0.031(4)
C32 0.109(4) 0.105(5) 0.083(4) -0.017(4) -0.019(3) 0.001(4)
C33 0.126(5) 0.136(5) 0.088(4) -0.032(4) 0.019(4) -0.040(4)
C34 0.091(4) 0.167(6) 0.159(6) 0.050(5) 0.002(4) 0.054(4)
C36 0.150(6) 0.136(6) 0.113(5) -0.031(5) -0.026(4) 0.013(5)
C38 0.145(10) 0.127(10) 0.072(7) -0.027(7) 0.013(7) 0.071(9)
C37 0.125(9) 0.155(12) 0.073(7) 0.011(8) 0.039(7) 0.038(9)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.389(5) . ?
O1 C21 1.462(5) . ?
O2 C11 1.392(5) . ?
O2 C28 1.444(5) . ?
O3 C9 1.333(5) . ?
O3 C24 1.435(5) . ?
O4 C16 1.401(5) . ?
O4 C30 1.445(5) . ?
N5 C18 1.345(5) . ?
N5 C10 1.430(5) . ?
N5 H5 0.9750 . ?
O6 C18 1.229(5) . ?
O7 C16 1.392(5) . ?
O7 C32 1.426(6) . ?
O8 C12 1.229(5) . ?
C9 O15 1.194(5) . ?
C9 C13 1.512(6) . ?
C10 C31 1.524(7) . ?
C10 C25 1.549(6) . ?
C10 C16 1.577(6) . ?
C11 C26 1.540(6) . ?
C11 C13 1.570(6) . ?
C12 N14 1.338(5) . ?
C12 C19 1.493(6) . ?
C13 N14 1.457(5) . ?
C13 C20 1.541(6) . ?
N14 H14 0.9812 . ?
C16 C27 1.538(7) . ?
O17 C31 1.262(7) . ?
O17 C38 1.535(10) . ?
C18 C22 1.485(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9601 . ?
C19 H19C 0.9599 . ?
C20 C26 1.523(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C21 C29 1.460(7) . ?
C21 H21A 0.9599 . ?
C21 H21B 0.9602 . ?
C22 H22A 0.9601 . ?
C22 H22B 0.9601 . ?
C22 H22C 0.9599 . ?
O23 C31 1.260(7) . ?
O23 C37 1.515(12) . ?
C24 H24A 0.9598 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9599 . ?
C25 C27 1.508(7) . ?
C25 H25A 0.9999 . ?
C25 H25B 0.9699 . ?
C26 H26A 0.9601 . ?
C26 H26B 0.9601 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9602 . ?
C28 C33 1.465(7) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9599 . ?
C29 H29C 0.9600 . ?
C30 C34 1.443(8) . ?
C30 H30A 0.9602 . ?
C30 H30B 0.9601 . ?
C32 C36 1.485(8) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C33 H33A 0.9601 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9599 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9601 . ?
C34 H34C 0.9598 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9601 . ?
C36 H36C 0.9599 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 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
C11 O1 C21 115.1(3) . . ?
C11 O2 C28 115.4(3) . . ?
C9 O3 C24 116.0(4) . . ?
C16 O4 C30 113.6(4) . . ?
C18 N5 C10 119.0(3) . . ?
C18 N5 H5 122.7 . . ?
C10 N5 H5 116.1 . . ?
C16 O7 C32 115.6(4) . . ?
O15 C9 O3 123.8(4) . . ?
O15 C9 C13 125.1(5) . . ?
O3 C9 C13 111.0(4) . . ?
N5 C10 C31 110.8(4) . . ?
N5 C10 C25 118.8(4) . . ?
C31 C10 C25 112.3(4) . . ?
N5 C10 C16 117.5(3) . . ?
C31 C10 C16 108.9(4) . . ?
C25 C10 C16 86.3(3) . . ?
O1 C11 O2 113.4(3) . . ?
O1 C11 C26 113.5(3) . . ?
O2 C11 C26 114.5(4) . . ?
O1 C11 C13 119.3(3) . . ?
O2 C11 C13 105.3(3) . . ?
C26 C11 C13 88.5(3) . . ?
O8 C12 N14 121.9(4) . . ?
O8 C12 C19 120.7(4) . . ?
N14 C12 C19 117.4(4) . . ?
N14 C13 C9 112.9(3) . . ?
N14 C13 C20 112.5(3) . . ?
C9 C13 C20 114.7(4) . . ?
N14 C13 C11 110.6(3) . . ?
C9 C13 C11 117.1(3) . . ?
C20 C13 C11 86.6(3) . . ?
C12 N14 C13 119.8(3) . . ?
C12 N14 H14 127.5 . . ?
C13 N14 H14 111.8 . . ?
O7 C16 O4 112.0(4) . . ?
O7 C16 C27 112.9(4) . . ?
O4 C16 C27 115.2(4) . . ?
O7 C16 C10 118.2(4) . . ?
O4 C16 C10 108.0(3) . . ?
C27 C16 C10 88.7(3) . . ?
C31 O17 C38 107.8(7) . . ?
O6 C18 N5 120.6(4) . . ?
O6 C18 C22 122.2(4) . . ?
N5 C18 C22 117.2(4) . . ?
C12 C19 H19A 109.8 . . ?
C12 C19 H19B 109.2 . . ?
H19A C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.4 . . ?
C26 C20 C13 90.2(3) . . ?
C26 C20 H20A 118.5 . . ?
C13 C20 H20A 109.9 . . ?
C26 C20 H20B 118.4 . . ?
C13 C20 H20B 108.0 . . ?
H20A C20 H20B 109.5 . . ?
C29 C21 O1 108.7(4) . . ?
C29 C21 H21A 111.0 . . ?
O1 C21 H21A 108.8 . . ?
C29 C21 H21B 109.6 . . ?
O1 C21 H21B 109.2 . . ?
H21A C21 H21B 109.5 . . ?
C18 C22 H22A 109.4 . . ?
C18 C22 H22B 109.9 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.1 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C31 O23 C37 105.7(7) . . ?
O3 C24 H24A 109.8 . . ?
O3 C24 H24B 109.3 . . ?
H24A C24 H24B 109.5 . . ?
O3 C24 H24C 109.4 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C27 C25 C10 90.9(4) . . ?
C27 C25 H25A 131.0 . . ?
C10 C25 H25A 105.3 . . ?
C27 C25 H25B 109.2 . . ?
C10 C25 H25B 110.0 . . ?
H25A C25 H25B 107.9 . . ?
C20 C26 C11 88.3(3) . . ?
C20 C26 H26A 118.9 . . ?
C11 C26 H26A 108.1 . . ?
C20 C26 H26B 119.5 . . ?
C11 C26 H26B 109.6 . . ?
H26A C26 H26B 109.5 . . ?
C25 C27 C16 89.1(4) . . ?
C25 C27 H27A 120.4 . . ?
C16 C27 H27A 109.7 . . ?
C25 C27 H27B 117.5 . . ?
C16 C27 H27B 107.8 . . ?
H27A C27 H27B 109.5 . . ?
O2 C28 C33 109.1(4) . . ?
O2 C28 H28A 108.2 . . ?
C33 C28 H28A 109.1 . . ?
O2 C28 H28B 109.7 . . ?
C33 C28 H28B 111.2 . . ?
H28A C28 H28B 109.5 . . ?
C21 C29 H29A 108.8 . . ?
C21 C29 H29B 109.3 . . ?
H29A C29 H29B 109.5 . . ?
C21 C29 H29C 110.3 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C34 C30 O4 111.2(5) . . ?
C34 C30 H30A 110.3 . . ?
O4 C30 H30A 109.5 . . ?
C34 C30 H30B 107.9 . . ?
O4 C30 H30B 108.4 . . ?
H30A C30 H30B 109.5 . . ?
O23 C31 O17 124.0(5) . . ?
O23 C31 C10 118.3(6) . . ?
O17 C31 C10 117.6(5) . . ?
O7 C32 C36 108.7(5) . . ?
O7 C32 H32A 110.2 . . ?
C36 C32 H32A 109.7 . . ?
O7 C32 H32B 108.8 . . ?
C36 C32 H32B 110.0 . . ?
H32A C32 H32B 109.5 . . ?
C28 C33 H33A 110.0 . . ?
C28 C33 H33B 108.9 . . ?
H33A C33 H33B 109.5 . . ?
C28 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C30 C34 H34A 110.4 . . ?
C30 C34 H34B 107.9 . . ?
H34A C34 H34B 109.5 . . ?
C30 C34 H34C 110.2 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C36 H36A 109.5 . . ?
C32 C36 H36B 109.3 . . ?
H36A C36 H36B 109.5 . . ?
C32 C36 H36C 109.6 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O17 C38 H38A 109.5 . . ?
O17 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O17 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O23 C37 H37A 109.5 . . ?
O23 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O23 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        21.02
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.027