# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Robin Bedford'
_publ_contact_author_email       R.BEDFORD@BRISTOL.AC.UK

_publ_section_title              
;
The catalytic ortho-arylation of tryosine
;
loop_
_publ_author_name
'Robin Bedford'
'Mairi F. Haddow'
'Charlotte J. Mitchell'
'Ruth L. Webster'

# Attachment 'rw093sad.cif'

data_rw093sad
_database_code_depnum_ccdc_archive 'CCDC 725600'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H35 N O6'
_chemical_formula_sum            'C27 H35 N O6'
_chemical_formula_weight         469.56

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
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   9.9888(10)
_cell_length_b                   10.6897(10)
_cell_length_c                   13.5774(13)
_cell_angle_alpha                85.729(6)
_cell_angle_beta                 68.552(5)
_cell_angle_gamma                71.738(5)
_cell_volume                     1280.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5244
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      29.94

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_crystal_preparation       
;
A single crystal was coated in high-vacuum grease and mounted
on a glass fibre.
;
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan'
_exptl_absorpt_correction_T_min  0.9143
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_process_details   'SADABS V2008/1'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21665
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5869
_reflns_number_gt                4427
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex II'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker ShelXTL'
_computing_publication_material  'Bruker ShelXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.3205P] 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         5869
_refine_ls_number_parameters     319
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.70680(11) 0.69280(9) 0.98652(7) 0.0235(2) Uani 1 1 d . . .
O2 O -0.13291(11) 0.08682(9) 0.87402(7) 0.0229(2) Uani 1 1 d . . .
H2 H -0.1833 0.1614 0.9045 0.034 Uiso 1 1 calc R . .
O3 O 0.30576(11) 0.29224(9) 0.54133(7) 0.0214(2) Uani 1 1 d . . .
O4 O 0.12466(11) 0.49195(9) 0.56630(8) 0.0262(2) Uani 1 1 d . . .
O5 O 0.40010(11) 0.10277(9) 0.23011(7) 0.0223(2) Uani 1 1 d . . .
O6 O 0.23203(11) 0.29718(9) 0.22348(8) 0.0233(2) Uani 1 1 d . . .
N1 N 0.16738(13) 0.34374(11) 0.43876(9) 0.0183(2) Uani 1 1 d D . .
H1N H 0.0858(15) 0.3952(14) 0.4276(12) 0.022 Uiso 1 1 d D . .
C1 C -0.84735(16) 0.54088(16) 1.04165(12) 0.0296(3) Uani 1 1 d . . .
H1A H -0.9293 0.6186 1.0803 0.044 Uiso 1 1 calc R . .
H1B H -0.8239 0.4752 1.0921 0.044 Uiso 1 1 calc R . .
H1C H -0.8788 0.5031 0.9934 0.044 Uiso 1 1 calc R . .
C2 C -0.70945(15) 0.58035(14) 0.97906(10) 0.0203(3) Uani 1 1 d . . .
C3 C -0.57340(15) 0.48056(13) 0.90637(10) 0.0174(3) Uani 1 1 d . . .
C4 C -0.55619(15) 0.34599(13) 0.91012(10) 0.0190(3) Uani 1 1 d . . .
H4 H -0.6371 0.3158 0.9550 0.023 Uiso 1 1 calc R . .
C5 C -0.42126(15) 0.25591(13) 0.84848(10) 0.0186(3) Uani 1 1 d . . .
H5 H -0.4102 0.1643 0.8524 0.022 Uiso 1 1 calc R . .
C6 C -0.30118(15) 0.29807(13) 0.78058(10) 0.0170(3) Uani 1 1 d . . .
C7 C -0.32178(15) 0.43339(13) 0.77339(10) 0.0177(3) Uani 1 1 d . . .
H7 H -0.2436 0.4641 0.7251 0.021 Uiso 1 1 calc R . .
C8 C -0.45550(15) 0.52293(13) 0.83624(10) 0.0178(3) Uani 1 1 d . . .
H8 H -0.4672 0.6146 0.8316 0.021 Uiso 1 1 calc R . .
C9 C -0.15400(14) 0.20198(12) 0.71769(10) 0.0163(3) Uani 1 1 d . . .
C10 C -0.07547(15) 0.10023(12) 0.76639(10) 0.0170(3) Uani 1 1 d . . .
C11 C 0.06390(15) 0.00874(12) 0.70679(10) 0.0175(3) Uani 1 1 d . . .
C12 C 0.11907(15) 0.02484(12) 0.59798(10) 0.0175(3) Uani 1 1 d . . .
H12 H 0.2123 -0.0360 0.5561 0.021 Uiso 1 1 calc R . .
C13 C 0.04471(15) 0.12543(12) 0.54740(10) 0.0165(3) Uani 1 1 d . . .
C14 C -0.09109(15) 0.21408(12) 0.60842(10) 0.0172(3) Uani 1 1 d . . .
H14 H -0.1424 0.2843 0.5755 0.021 Uiso 1 1 calc R . .
C15 C 0.15039(16) -0.10238(13) 0.76020(11) 0.0207(3) Uani 1 1 d . . .
C16 C 0.19376(17) -0.04328(14) 0.83966(12) 0.0257(3) Uani 1 1 d . . .
H16A H 0.1020 0.0117 0.8938 0.039 Uiso 1 1 calc R . .
H16B H 0.2585 0.0108 0.8023 0.039 Uiso 1 1 calc R . .
H16C H 0.2484 -0.1146 0.8735 0.039 Uiso 1 1 calc R . .
C17 C 0.05352(17) -0.19207(14) 0.81728(12) 0.0267(3) Uani 1 1 d . . .
H17A H 0.1102 -0.2621 0.8508 0.040 Uiso 1 1 calc R . .
H17B H 0.0289 -0.2314 0.7658 0.040 Uiso 1 1 calc R . .
H17C H -0.0401 -0.1397 0.8715 0.040 Uiso 1 1 calc R . .
C18 C 0.29789(17) -0.19022(14) 0.67877(12) 0.0294(3) Uani 1 1 d . . .
H18A H 0.3497 -0.2600 0.7153 0.044 Uiso 1 1 calc R . .
H18B H 0.3636 -0.1366 0.6423 0.044 Uiso 1 1 calc R . .
H18C H 0.2743 -0.2300 0.6269 0.044 Uiso 1 1 calc R . .
C19 C 0.10904(15) 0.13655(13) 0.42871(10) 0.0180(3) Uani 1 1 d . . .
H19A H 0.0256 0.1839 0.4039 0.022 Uiso 1 1 calc R . .
H19B H 0.1554 0.0469 0.3944 0.022 Uiso 1 1 calc R . .
C20 C 0.22909(15) 0.20987(12) 0.39371(10) 0.0164(3) Uani 1 1 d . . .
H20 H 0.3155 0.1605 0.4162 0.020 Uiso 1 1 calc R . .
C21 C 0.19360(15) 0.38392(13) 0.52003(11) 0.0190(3) Uani 1 1 d . . .
C22 C 0.33924(15) 0.30565(13) 0.63667(10) 0.0200(3) Uani 1 1 d . . .
C23 C 0.40748(17) 0.41659(14) 0.62521(12) 0.0270(3) Uani 1 1 d . . .
H23A H 0.4956 0.4019 0.5592 0.041 Uiso 1 1 calc R . .
H23B H 0.4388 0.4189 0.6853 0.041 Uiso 1 1 calc R . .
H23C H 0.3321 0.5007 0.6237 0.041 Uiso 1 1 calc R . .
C24 C 0.19766(16) 0.32410(15) 0.73487(11) 0.0267(3) Uani 1 1 d . . .
H24A H 0.1275 0.4127 0.7374 0.040 Uiso 1 1 calc R . .
H24B H 0.2248 0.3134 0.7981 0.040 Uiso 1 1 calc R . .
H24C H 0.1492 0.2581 0.7326 0.040 Uiso 1 1 calc R . .
C25 C 0.45523(17) 0.17278(14) 0.63442(12) 0.0266(3) Uani 1 1 d . . .
H25A H 0.4109 0.1023 0.6368 0.040 Uiso 1 1 calc R . .
H25B H 0.4855 0.1689 0.6958 0.040 Uiso 1 1 calc R . .
H25C H 0.5441 0.1615 0.5692 0.040 Uiso 1 1 calc R . .
C26 C 0.28506(15) 0.21221(12) 0.27366(10) 0.0169(3) Uani 1 1 d . . .
C27 C 0.45613(18) 0.09103(14) 0.11584(11) 0.0263(3) Uani 1 1 d . . .
H27A H 0.3750 0.0888 0.0924 0.039 Uiso 1 1 calc R . .
H27B H 0.5408 0.0095 0.0912 0.039 Uiso 1 1 calc R . .
H27C H 0.4906 0.1668 0.0864 0.039 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0247(5) 0.0225(5) 0.0182(5) 0.0001(4) -0.0077(4) -0.0003(4)
O2 0.0268(6) 0.0216(5) 0.0133(5) 0.0023(4) -0.0041(4) -0.0022(4)
O3 0.0229(5) 0.0214(5) 0.0195(5) -0.0036(4) -0.0119(4) -0.0003(4)
O4 0.0289(6) 0.0202(5) 0.0304(6) -0.0058(4) -0.0172(5) 0.0006(4)
O5 0.0252(5) 0.0221(5) 0.0136(5) -0.0016(4) -0.0037(4) -0.0024(4)
O6 0.0268(5) 0.0236(5) 0.0192(5) 0.0048(4) -0.0090(4) -0.0074(4)
N1 0.0202(6) 0.0158(6) 0.0199(6) 0.0008(4) -0.0108(5) -0.0028(5)
C1 0.0176(7) 0.0391(9) 0.0258(8) -0.0009(6) -0.0029(6) -0.0055(7)
C2 0.0188(7) 0.0266(7) 0.0148(6) 0.0028(5) -0.0091(6) -0.0026(6)
C3 0.0161(7) 0.0219(7) 0.0148(6) 0.0011(5) -0.0079(5) -0.0042(5)
C4 0.0167(7) 0.0252(7) 0.0171(7) 0.0043(5) -0.0063(5) -0.0095(6)
C5 0.0211(7) 0.0172(6) 0.0190(7) 0.0031(5) -0.0086(6) -0.0068(5)
C6 0.0174(7) 0.0197(6) 0.0140(6) 0.0020(5) -0.0072(5) -0.0046(5)
C7 0.0180(7) 0.0201(7) 0.0148(6) 0.0026(5) -0.0049(5) -0.0074(5)
C8 0.0200(7) 0.0174(6) 0.0167(6) 0.0017(5) -0.0082(5) -0.0053(5)
C9 0.0169(7) 0.0155(6) 0.0158(6) -0.0003(5) -0.0047(5) -0.0054(5)
C10 0.0196(7) 0.0184(6) 0.0132(6) 0.0013(5) -0.0048(5) -0.0074(5)
C11 0.0193(7) 0.0160(6) 0.0184(7) 0.0011(5) -0.0081(6) -0.0055(5)
C12 0.0150(6) 0.0167(6) 0.0179(7) -0.0024(5) -0.0030(5) -0.0036(5)
C13 0.0191(7) 0.0177(6) 0.0141(6) 0.0002(5) -0.0052(5) -0.0083(5)
C14 0.0194(7) 0.0162(6) 0.0166(6) 0.0019(5) -0.0070(5) -0.0059(5)
C15 0.0207(7) 0.0196(7) 0.0199(7) 0.0033(5) -0.0081(6) -0.0034(6)
C16 0.0284(8) 0.0268(7) 0.0257(8) 0.0073(6) -0.0151(7) -0.0086(6)
C17 0.0314(8) 0.0219(7) 0.0299(8) 0.0092(6) -0.0154(7) -0.0090(6)
C18 0.0266(8) 0.0246(8) 0.0286(8) 0.0027(6) -0.0108(7) 0.0040(6)
C19 0.0204(7) 0.0183(6) 0.0152(6) -0.0001(5) -0.0056(5) -0.0067(5)
C20 0.0182(7) 0.0156(6) 0.0135(6) 0.0002(5) -0.0048(5) -0.0040(5)
C21 0.0202(7) 0.0186(7) 0.0185(7) 0.0005(5) -0.0084(6) -0.0047(6)
C22 0.0218(7) 0.0238(7) 0.0157(7) -0.0008(5) -0.0092(6) -0.0053(6)
C23 0.0304(8) 0.0289(8) 0.0279(8) 0.0038(6) -0.0152(7) -0.0125(7)
C24 0.0240(8) 0.0324(8) 0.0202(7) 0.0002(6) -0.0054(6) -0.0071(6)
C25 0.0264(8) 0.0274(8) 0.0250(8) 0.0016(6) -0.0135(6) -0.0023(6)
C26 0.0180(7) 0.0177(6) 0.0172(7) 0.0003(5) -0.0058(5) -0.0088(5)
C27 0.0325(8) 0.0281(8) 0.0130(7) -0.0025(5) -0.0019(6) -0.0092(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2230(16) . ?
O2 C10 1.3757(15) . ?
O2 H2 0.8400 . ?
O3 C21 1.3439(16) . ?
O3 C22 1.4772(16) . ?
O4 C21 1.2230(16) . ?
O5 C26 1.3425(16) . ?
O5 C27 1.4444(16) . ?
O6 C26 1.1999(16) . ?
N1 C21 1.3501(17) . ?
N1 C20 1.4505(16) . ?
N1 H1N 0.887(13) . ?
C1 C2 1.501(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.4920(19) . ?
C3 C4 1.3935(18) . ?
C3 C8 1.3960(18) . ?
C4 C5 1.3878(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.4000(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.3969(18) . ?
C6 C9 1.4872(18) . ?
C7 C8 1.3840(18) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.3976(18) . ?
C9 C10 1.4046(18) . ?
C10 C11 1.4107(18) . ?
C11 C12 1.3935(18) . ?
C11 C15 1.5395(18) . ?
C12 C13 1.3936(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3835(18) . ?
C13 C19 1.5119(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.538(2) . ?
C15 C18 1.540(2) . ?
C15 C17 1.5422(19) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.5475(17) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C26 1.5187(18) . ?
C20 H20 1.0000 . ?
C22 C23 1.5155(19) . ?
C22 C24 1.5173(19) . ?
C22 C25 1.5198(19) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 H2 109.5 . . ?
C21 O3 C22 121.28(10) . . ?
C26 O5 C27 115.17(10) . . ?
C21 N1 C20 124.51(11) . . ?
C21 N1 H1N 115.3(10) . . ?
C20 N1 H1N 117.1(10) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 119.51(12) . . ?
O1 C2 C1 121.16(13) . . ?
C3 C2 C1 119.33(12) . . ?
C4 C3 C8 118.84(12) . . ?
C4 C3 C2 122.36(12) . . ?
C8 C3 C2 118.70(12) . . ?
C5 C4 C3 120.22(12) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.95(12) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 118.52(12) . . ?
C7 C6 C9 120.20(11) . . ?
C5 C6 C9 121.28(11) . . ?
C8 C7 C6 120.37(12) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C3 120.99(12) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C14 C9 C10 119.22(12) . . ?
C14 C9 C6 119.60(11) . . ?
C10 C9 C6 121.17(11) . . ?
O2 C10 C9 120.73(12) . . ?
O2 C10 C11 118.03(11) . . ?
C9 C10 C11 121.24(12) . . ?
C12 C11 C10 116.68(12) . . ?
C12 C11 C15 122.06(12) . . ?
C10 C11 C15 121.26(11) . . ?
C13 C12 C11 123.50(12) . . ?
C13 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
C14 C13 C12 118.28(12) . . ?
C14 C13 C19 120.64(12) . . ?
C12 C13 C19 121.07(12) . . ?
C13 C14 C9 121.07(12) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
C16 C15 C18 107.32(12) . . ?
C16 C15 C11 110.02(11) . . ?
C18 C15 C11 111.59(11) . . ?
C16 C15 C17 109.97(11) . . ?
C18 C15 C17 107.31(12) . . ?
C11 C15 C17 110.55(11) . . ?
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 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C19 C20 113.03(10) . . ?
C13 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
C13 C19 H19B 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
N1 C20 C26 109.63(10) . . ?
N1 C20 C19 111.93(11) . . ?
C26 C20 C19 107.41(10) . . ?
N1 C20 H20 109.3 . . ?
C26 C20 H20 109.3 . . ?
C19 C20 H20 109.3 . . ?
O4 C21 O3 124.93(12) . . ?
O4 C21 N1 123.37(12) . . ?
O3 C21 N1 111.69(11) . . ?
O3 C22 C23 110.05(11) . . ?
O3 C22 C24 109.96(11) . . ?
C23 C22 C24 112.85(12) . . ?
O3 C22 C25 101.69(10) . . ?
C23 C22 C25 110.93(12) . . ?
C24 C22 C25 110.81(12) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O6 C26 O5 123.95(12) . . ?
O6 C26 C20 125.45(12) . . ?
O5 C26 C20 110.56(11) . . ?
O5 C27 H27A 109.5 . . ?
O5 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O5 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 166.19(12) . . . . ?
C1 C2 C3 C4 -13.91(19) . . . . ?
O1 C2 C3 C8 -10.12(19) . . . . ?
C1 C2 C3 C8 169.79(12) . . . . ?
C8 C3 C4 C5 2.89(19) . . . . ?
C2 C3 C4 C5 -173.41(12) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C4 C5 C6 C7 -2.16(19) . . . . ?
C4 C5 C6 C9 177.38(12) . . . . ?
C5 C6 C7 C8 3.23(19) . . . . ?
C9 C6 C7 C8 -176.31(12) . . . . ?
C6 C7 C8 C3 -1.3(2) . . . . ?
C4 C3 C8 C7 -1.82(19) . . . . ?
C2 C3 C8 C7 174.62(12) . . . . ?
C7 C6 C9 C14 -52.52(17) . . . . ?
C5 C6 C9 C14 127.94(14) . . . . ?
C7 C6 C9 C10 126.42(14) . . . . ?
C5 C6 C9 C10 -53.11(17) . . . . ?
C14 C9 C10 O2 178.91(11) . . . . ?
C6 C9 C10 O2 -0.04(18) . . . . ?
C14 C9 C10 C11 -1.28(18) . . . . ?
C6 C9 C10 C11 179.78(11) . . . . ?
O2 C10 C11 C12 179.95(11) . . . . ?
C9 C10 C11 C12 0.13(18) . . . . ?
O2 C10 C11 C15 -0.49(18) . . . . ?
C9 C10 C11 C15 179.69(12) . . . . ?
C10 C11 C12 C13 0.51(19) . . . . ?
C15 C11 C12 C13 -179.04(12) . . . . ?
C11 C12 C13 C14 0.02(19) . . . . ?
C11 C12 C13 C19 -179.01(12) . . . . ?
C12 C13 C14 C9 -1.22(18) . . . . ?
C19 C13 C14 C9 177.82(12) . . . . ?
C10 C9 C14 C13 1.84(19) . . . . ?
C6 C9 C14 C13 -179.20(11) . . . . ?
C12 C11 C15 C16 117.83(14) . . . . ?
C10 C11 C15 C16 -61.70(16) . . . . ?
C12 C11 C15 C18 -1.18(18) . . . . ?
C10 C11 C15 C18 179.29(12) . . . . ?
C12 C11 C15 C17 -120.52(14) . . . . ?
C10 C11 C15 C17 59.95(16) . . . . ?
C14 C13 C19 C20 97.26(14) . . . . ?
C12 C13 C19 C20 -83.73(15) . . . . ?
C21 N1 C20 C26 -136.50(13) . . . . ?
C21 N1 C20 C19 104.41(14) . . . . ?
C13 C19 C20 N1 -60.35(14) . . . . ?
C13 C19 C20 C26 179.27(11) . . . . ?
C22 O3 C21 O4 10.6(2) . . . . ?
C22 O3 C21 N1 -170.80(11) . . . . ?
C20 N1 C21 O4 -169.57(13) . . . . ?
C20 N1 C21 O3 11.79(18) . . . . ?
C21 O3 C22 C23 -70.20(15) . . . . ?
C21 O3 C22 C24 54.71(15) . . . . ?
C21 O3 C22 C25 172.17(11) . . . . ?
C27 O5 C26 O6 -1.42(18) . . . . ?
C27 O5 C26 C20 176.40(11) . . . . ?
N1 C20 C26 O6 -31.41(18) . . . . ?
C19 C20 C26 O6 90.42(15) . . . . ?
N1 C20 C26 O5 150.81(11) . . . . ?
C19 C20 C26 O5 -87.36(12) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.042