# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2005



data_global

_journal_coden_Cambridge         177
_journal_volume                  ?
_journal_year                    ?
_journal_page_first              ?

_publ_requested_journal          'Organic & Biomolecular Chemistry'

loop_
_publ_author_name
C.Moody
'Mark C. Bagley'
'Franck Lach'
'Francine N. Palmer'
'Adrian G. Pepper'
'Cyril Poriel'
'Alexandra M.Z. Slawin'

_publ_contact_author_name        'Christopher Moody'
_publ_contact_author_address     
;
School of Chemistry
University of Nottingham
University Park
Nottingham
NG7 2RD
UNITED KINGDOM
;

_publ_contact_author_email       C.J.MOODY@NOTTINGHAM.AC.UK

_publ_section_title              
;
The diazo route to diazonamide A. Part 2.1 Studies on
the tyrosine-derived fragment
;

data_cmex42
_database_code_depnum_ccdc_archive 'CCDC 279634'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
-
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N O4'
_chemical_formula_sum            'C10 H9 N O4'
_chemical_formula_weight         207.18

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)/n

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

_cell_length_a                   10.244(2)
_cell_length_b                   13.920(3)
_cell_length_c                   13.155(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.4243(17)
_cell_angle_gamma                90.00
_cell_volume                     1874.1(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    6196
_cell_measurement_theta_min      1.9906
_cell_measurement_theta_max      26.3714

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.1000
_exptl_crystal_size_mid          0.1000
_exptl_crystal_size_min          0.0500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8375
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 0.83
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11668
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.35
_reflns_number_total             3344
_reflns_number_gt                2820
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_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^)+(0.0514P)^2^+0.3044P] 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     SHELXL
_refine_ls_extinction_coef       0.0005(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3344
_refine_ls_number_parameters     282
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.87525(9) 0.23099(7) 0.19937(7) 0.0220(3) Uani 1 1 d . . .
O2 O 0.91394(9) 0.19369(7) 0.35783(8) 0.0244(3) Uani 1 1 d . . .
N1 N 0.87268(10) 0.24850(8) 0.29099(9) 0.0168(3) Uani 1 1 d . . .
C1 C 0.82124(12) 0.34224(10) 0.32182(10) 0.0146(3) Uani 1 1 d . . .
C2 C 0.72145(12) 0.38641(10) 0.26293(10) 0.0139(3) Uani 1 1 d . . .
C3 C 0.68631(13) 0.47858(10) 0.29344(10) 0.0156(3) Uani 1 1 d . . .
H3A H 0.6208 0.5125 0.2547 0.019 Uiso 1 1 calc R . .
C4 C 0.74439(13) 0.52185(10) 0.37859(10) 0.0184(3) Uani 1 1 d . . .
H4A H 0.7198 0.5852 0.3966 0.022 Uiso 1 1 calc R . .
C5 C 0.83806(13) 0.47346(10) 0.43759(11) 0.0196(3) Uani 1 1 d . . .
H5A H 0.8749 0.5023 0.4976 0.023 Uiso 1 1 calc R . .
C6 C 0.87782(13) 0.38270(10) 0.40864(10) 0.0178(3) Uani 1 1 d . . .
H6A H 0.9429 0.3490 0.4479 0.021 Uiso 1 1 calc R . .
C7 C 0.64449(12) 0.33880(10) 0.17827(10) 0.0147(3) Uani 1 1 d . . .
C8 C 0.58804(12) 0.24394(10) 0.20336(10) 0.0146(3) Uani 1 1 d . . .
O8 O 0.60692(9) 0.20607(7) 0.28689(7) 0.0183(2) Uani 1 1 d . . .
O9 O 0.51505(9) 0.20382(7) 0.12992(7) 0.0208(3) Uani 1 1 d D . .
H9O H 0.4784(17) 0.1437(7) 0.1549(14) 0.057(6) Uiso 1 1 d D . .
C9 C 0.61692(13) 0.37980(10) 0.08788(10) 0.0180(3) Uani 1 1 d . . .
H9A H 0.5596 0.3457 0.0422 0.022 Uiso 1 1 calc R . .
C10 C 0.66747(15) 0.47390(10) 0.05186(11) 0.0230(3) Uani 1 1 d . . .
H10A H 0.6048 0.5248 0.0664 0.034 Uiso 1 1 calc R . .
H10B H 0.6793 0.4708 -0.0216 0.034 Uiso 1 1 calc R . .
H10C H 0.7515 0.4879 0.0872 0.034 Uiso 1 1 calc R . .
O11 O 0.13912(9) 0.04326(7) 0.27968(7) 0.0217(3) Uani 1 1 d . . .
O12 O 0.09909(9) 0.06965(7) 0.11905(7) 0.0244(3) Uani 1 1 d . . .
N11 N 0.13520(10) 0.01782(8) 0.19015(9) 0.0166(3) Uani 1 1 d . . .
C11 C 0.17207(12) -0.08117(10) 0.16729(10) 0.0150(3) Uani 1 1 d . . .
C12 C 0.27005(12) -0.12728(10) 0.22619(10) 0.0148(3) Uani 1 1 d . . .
C13 C 0.29453(13) -0.22278(10) 0.20146(10) 0.0164(3) Uani 1 1 d . . .
H13A H 0.3597 -0.2574 0.2397 0.020 Uiso 1 1 calc R . .
C14 C 0.22595(13) -0.26834(10) 0.12232(10) 0.0192(3) Uani 1 1 d . . .
H14A H 0.2442 -0.3337 0.1075 0.023 Uiso 1 1 calc R . .
C15 C 0.13128(13) -0.21985(10) 0.06456(11) 0.0201(3) Uani 1 1 d . . .
H15A H 0.0859 -0.2513 0.0096 0.024 Uiso 1 1 calc R . .
C16 C 0.10313(13) -0.12542(10) 0.08732(10) 0.0176(3) Uani 1 1 d . . .
H16A H 0.0376 -0.0914 0.0488 0.021 Uiso 1 1 calc R . .
C17 C 0.35328(12) -0.08042(10) 0.30794(10) 0.0147(3) Uani 1 1 d . . .
C18 C 0.42308(12) 0.00777(10) 0.27833(10) 0.0147(3) Uani 1 1 d . . .
O18 O 0.40878(9) 0.04312(7) 0.19292(7) 0.0183(2) Uani 1 1 d . . .
O19 O 0.50037(9) 0.04641(7) 0.35011(7) 0.0209(3) Uani 1 1 d D . .
H19O H 0.5383(17) 0.1057(7) 0.3240(13) 0.057(6) Uiso 1 1 d D . .
C19 C 0.37027(13) -0.11620(10) 0.40200(10) 0.0171(3) Uani 1 1 d . . .
H19A H 0.4326 -0.0848 0.4459 0.021 Uiso 1 1 calc R . .
C20 C 0.30140(14) -0.20031(11) 0.44481(11) 0.0219(3) Uani 1 1 d . . .
H20A H 0.2204 -0.2123 0.4045 0.033 Uiso 1 1 calc R . .
H20B H 0.2808 -0.1869 0.5155 0.033 Uiso 1 1 calc R . .
H20C H 0.3578 -0.2571 0.4426 0.033 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 0.0223(5) 0.0223(6) 0.0215(6) -0.0044(4) 0.0013(4) 0.0015(4)
O2 0.0244(6) 0.0189(6) 0.0298(6) 0.0085(5) 0.0010(4) 0.0043(4)
N1 0.0138(6) 0.0149(7) 0.0216(7) 0.0006(5) 0.0005(5) -0.0028(5)
C1 0.0148(7) 0.0128(7) 0.0163(7) 0.0016(5) 0.0025(5) -0.0021(5)
C2 0.0131(7) 0.0143(7) 0.0143(7) 0.0004(5) 0.0030(5) -0.0032(5)
C3 0.0149(7) 0.0159(7) 0.0159(7) 0.0020(6) 0.0013(5) 0.0005(6)
C4 0.0216(8) 0.0155(8) 0.0183(7) -0.0032(6) 0.0049(6) -0.0020(6)
C5 0.0211(8) 0.0217(8) 0.0157(7) -0.0018(6) -0.0014(6) -0.0052(6)
C6 0.0172(7) 0.0186(8) 0.0175(7) 0.0045(6) -0.0024(6) -0.0029(6)
C7 0.0132(7) 0.0141(8) 0.0169(7) -0.0016(6) 0.0005(5) 0.0001(5)
C8 0.0130(7) 0.0159(8) 0.0149(7) -0.0029(6) -0.0008(5) 0.0005(5)
O8 0.0205(5) 0.0182(5) 0.0160(5) 0.0016(4) -0.0021(4) -0.0045(4)
O9 0.0255(6) 0.0175(6) 0.0187(5) 0.0014(4) -0.0062(4) -0.0068(4)
C9 0.0205(7) 0.0159(8) 0.0174(7) -0.0025(6) -0.0011(6) 0.0002(6)
C10 0.0321(9) 0.0194(8) 0.0171(8) 0.0018(6) -0.0024(6) -0.0030(6)
O11 0.0212(5) 0.0213(6) 0.0225(6) -0.0060(4) -0.0020(4) 0.0037(4)
O12 0.0268(6) 0.0193(6) 0.0265(6) 0.0070(5) -0.0047(4) 0.0037(4)
N11 0.0130(6) 0.0172(7) 0.0193(7) 0.0010(5) -0.0017(5) 0.0000(5)
C11 0.0152(7) 0.0125(7) 0.0176(7) -0.0004(6) 0.0035(5) -0.0020(5)
C12 0.0140(7) 0.0164(8) 0.0141(7) 0.0016(6) 0.0032(5) -0.0022(6)
C13 0.0158(7) 0.0150(7) 0.0186(7) 0.0001(6) 0.0022(5) -0.0001(6)
C14 0.0230(8) 0.0143(8) 0.0206(8) -0.0025(6) 0.0046(6) -0.0019(6)
C15 0.0230(8) 0.0204(8) 0.0169(7) -0.0043(6) -0.0005(6) -0.0085(6)
C16 0.0162(7) 0.0202(8) 0.0162(7) 0.0034(6) -0.0020(5) -0.0025(6)
C17 0.0132(7) 0.0139(7) 0.0170(7) -0.0004(6) -0.0001(5) 0.0006(5)
C18 0.0122(7) 0.0150(7) 0.0168(7) -0.0018(6) -0.0005(5) 0.0025(5)
O18 0.0194(5) 0.0191(6) 0.0163(5) 0.0013(4) -0.0009(4) -0.0041(4)
O19 0.0242(6) 0.0183(6) 0.0195(5) 0.0024(4) -0.0067(4) -0.0074(4)
C19 0.0152(7) 0.0168(8) 0.0191(8) -0.0012(6) -0.0014(5) 0.0002(6)
C20 0.0266(8) 0.0209(8) 0.0181(8) 0.0021(6) -0.0002(6) -0.0042(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 N1 1.2311(14) . ?
O2 N1 1.2257(14) . ?
N1 C1 1.4707(18) . ?
C1 C6 1.3790(19) . ?
C1 C2 1.3986(18) . ?
C2 C3 1.3960(19) . ?
C2 C7 1.4922(18) . ?
C3 C4 1.3838(19) . ?
C3 H3A 0.9500 . ?
C4 C5 1.383(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C9 1.3383(19) . ?
C7 C8 1.4843(19) . ?
C8 O8 1.2267(15) . ?
C8 O9 1.3204(16) . ?
O9 H9O 0.9798(11) . ?
C9 C10 1.493(2) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O11 N11 1.2289(14) . ?
O12 N11 1.2259(14) . ?
N11 C11 1.4634(18) . ?
C11 C16 1.3864(19) . ?
C11 C12 1.3978(19) . ?
C12 C13 1.3938(19) . ?
C12 C17 1.4938(18) . ?
C13 C14 1.3849(19) . ?
C13 H13A 0.9500 . ?
C14 C15 1.382(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.381(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C19 1.3384(19) . ?
C17 C18 1.4810(19) . ?
C18 O18 1.2297(16) . ?
C18 O19 1.3208(16) . ?
O19 H19O 0.9800(11) . ?
C19 C20 1.4897(19) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N1 O1 123.93(12) . . ?
O2 N1 C1 118.11(11) . . ?
O1 N1 C1 117.92(11) . . ?
C6 C1 C2 123.43(13) . . ?
C6 C1 N1 116.60(12) . . ?
C2 C1 N1 119.96(12) . . ?
C3 C2 C1 115.85(12) . . ?
C3 C2 C7 119.23(12) . . ?
C1 C2 C7 124.66(12) . . ?
C4 C3 C2 121.70(13) . . ?
C4 C3 H3A 119.2 . . ?
C2 C3 H3A 119.2 . . ?
C5 C4 C3 120.43(13) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C4 C5 C6 119.64(13) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 H5A 120.2 . . ?
C1 C6 C5 118.81(13) . . ?
C1 C6 H6A 120.6 . . ?
C5 C6 H6A 120.6 . . ?
C9 C7 C8 120.49(12) . . ?
C9 C7 C2 123.96(13) . . ?
C8 C7 C2 115.32(11) . . ?
O8 C8 O9 122.45(12) . . ?
O8 C8 C7 122.24(12) . . ?
O9 C8 C7 115.31(11) . . ?
C8 O9 H9O 109.2(11) . . ?
C7 C9 C10 126.38(13) . . ?
C7 C9 H9A 116.8 . . ?
C10 C9 H9A 116.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O12 N11 O11 123.93(12) . . ?
O12 N11 C11 118.01(11) . . ?
O11 N11 C11 118.03(11) . . ?
C16 C11 C12 123.19(13) . . ?
C16 C11 N11 116.53(12) . . ?
C12 C11 N11 120.27(12) . . ?
C13 C12 C11 116.15(12) . . ?
C13 C12 C17 118.79(12) . . ?
C11 C12 C17 124.97(12) . . ?
C14 C13 C12 121.44(13) . . ?
C14 C13 H13A 119.3 . . ?
C12 C13 H13A 119.3 . . ?
C15 C14 C13 120.76(13) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C16 C15 C14 119.58(13) . . ?
C16 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?
C15 C16 C11 118.88(13) . . ?
C15 C16 H16A 120.6 . . ?
C11 C16 H16A 120.6 . . ?
C19 C17 C18 120.41(12) . . ?
C19 C17 C12 123.44(12) . . ?
C18 C17 C12 116.09(11) . . ?
O18 C18 O19 122.33(12) . . ?
O18 C18 C17 122.13(12) . . ?
O19 C18 C17 115.54(12) . . ?
C18 O19 H19O 109.1(11) . . ?
C17 C19 C20 126.64(13) . . ?
C17 C19 H19A 116.7 . . ?
C20 C19 H19A 116.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N1 C1 C6 31.70(16) . . . . ?
O1 N1 C1 C6 -146.18(12) . . . . ?
O2 N1 C1 C2 -149.35(12) . . . . ?
O1 N1 C1 C2 32.77(17) . . . . ?
C6 C1 C2 C3 3.90(19) . . . . ?
N1 C1 C2 C3 -174.97(11) . . . . ?
C6 C1 C2 C7 -170.23(12) . . . . ?
N1 C1 C2 C7 10.90(19) . . . . ?
C1 C2 C3 C4 -1.88(18) . . . . ?
C7 C2 C3 C4 172.59(12) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C3 C4 C5 C6 2.8(2) . . . . ?
C2 C1 C6 C5 -2.6(2) . . . . ?
N1 C1 C6 C5 176.30(12) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C3 C2 C7 C9 50.89(18) . . . . ?
C1 C2 C7 C9 -135.16(15) . . . . ?
C3 C2 C7 C8 -123.66(13) . . . . ?
C1 C2 C7 C8 50.29(17) . . . . ?
C9 C7 C8 O8 -176.98(13) . . . . ?
C2 C7 C8 O8 -2.22(18) . . . . ?
C9 C7 C8 O9 2.30(18) . . . . ?
C2 C7 C8 O9 177.06(11) . . . . ?
C8 C7 C9 C10 -179.28(13) . . . . ?
C2 C7 C9 C10 6.4(2) . . . . ?
O12 N11 C11 C16 -34.01(16) . . . . ?
O11 N11 C11 C16 144.18(12) . . . . ?
O12 N11 C11 C12 147.46(12) . . . . ?
O11 N11 C11 C12 -34.36(17) . . . . ?
C16 C11 C12 C13 -1.10(19) . . . . ?
N11 C11 C12 C13 177.33(11) . . . . ?
C16 C11 C12 C17 175.32(12) . . . . ?
N11 C11 C12 C17 -6.25(19) . . . . ?
C11 C12 C13 C14 0.59(18) . . . . ?
C17 C12 C13 C14 -176.06(12) . . . . ?
C12 C13 C14 C15 0.5(2) . . . . ?
C13 C14 C15 C16 -1.2(2) . . . . ?
C14 C15 C16 C11 0.7(2) . . . . ?
C12 C11 C16 C15 0.5(2) . . . . ?
N11 C11 C16 C15 -178.02(11) . . . . ?
C13 C12 C17 C19 -54.73(18) . . . . ?
C11 C12 C17 C19 128.94(15) . . . . ?
C13 C12 C17 C18 122.57(13) . . . . ?
C11 C12 C17 C18 -53.76(17) . . . . ?
C19 C17 C18 O18 -179.27(13) . . . . ?
C12 C17 C18 O18 3.34(18) . . . . ?
C19 C17 C18 O19 -0.04(18) . . . . ?
C12 C17 C18 O19 -177.43(11) . . . . ?
C18 C17 C19 C20 176.06(12) . . . . ?
C12 C17 C19 C20 -6.7(2) . . . . ?

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
O9 H9O O18 0.9798(11) 1.658(2) 2.6367(14) 176.7(18) .
O19 H19O O8 0.9800(11) 1.648(2) 2.6265(14) 176.5(18) .

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.045