# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Yan Zhang'
_publ_contact_author_email       njuzy@nju.edu.cn
loop_
_publ_author_name
'Dongdong Wu'
'Mingtao He'
'Wei Wang'
'Jie Zhou'
'Lei Wang'
'Hoong-Kun Fun'
'Jian-Hua Xu'
'Yan Zhang'

data_mo_wdd30_0m
_database_code_depnum_ccdc_archive 'CCDC 838079'
#TrackingRef '- compound 2.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 N2 O6'
_chemical_formula_sum            'C26 H22 N2 O6'
_chemical_formula_weight         458.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   15.6780(6)
_cell_length_b                   9.3043(6)
_cell_length_c                   30.2382(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.663(2)
_cell_angle_gamma                90.00
_cell_volume                     4267.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      32.60
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1920
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9585
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100.0(1)
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40080
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         32.69
_reflns_number_total             7753
_reflns_number_gt                6551
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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^)+(0.0654P)^2^+2.2018P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7753
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.08257(5) 1.03235(7) 0.04801(2) 0.02032(14) Uani 1 1 d . . .
O2 O 0.15626(8) 0.80463(10) -0.05493(3) 0.0412(2) Uani 1 1 d . . .
O3 O 0.04444(4) 0.83442(7) 0.11497(2) 0.01440(12) Uani 1 1 d . . .
O4 O 0.06605(6) 1.27408(8) 0.15329(3) 0.02689(16) Uani 1 1 d . . .
O5 O 0.10487(4) 0.85068(7) 0.19486(2) 0.01451(12) Uani 1 1 d . . .
O6 O 0.22642(4) 0.70661(7) 0.15134(2) 0.01460(12) Uani 1 1 d . . .
N1 N 0.12404(5) 0.82775(8) 0.01355(3) 0.01655(14) Uani 1 1 d . . .
N2 N 0.12014(5) 1.04890(8) 0.15157(3) 0.01396(13) Uani 1 1 d . . .
C1 C 0.10302(6) 0.90719(9) 0.04896(3) 0.01479(15) Uani 1 1 d . . .
C2 C 0.11881(6) 0.67746(10) 0.02308(3) 0.01610(15) Uani 1 1 d . . .
C3 C 0.12221(7) 0.56046(11) -0.00483(3) 0.02167(18) Uani 1 1 d . . .
H3A H 0.1322 0.5722 -0.0336 0.026 Uiso 1 1 calc R . .
C4 C 0.11003(7) 0.42458(11) 0.01200(4) 0.02316(19) Uani 1 1 d . . .
H4A H 0.1122 0.3444 -0.0061 0.028 Uiso 1 1 calc R . .
C5 C 0.09483(7) 0.40508(10) 0.05491(3) 0.02125(18) Uani 1 1 d . . .
H5A H 0.0859 0.3131 0.0650 0.025 Uiso 1 1 calc R . .
C6 C 0.09292(6) 0.52362(9) 0.08291(3) 0.01773(16) Uani 1 1 d . . .
H6A H 0.0838 0.5118 0.1119 0.021 Uiso 1 1 calc R . .
C7 C 0.10486(6) 0.65930(9) 0.06661(3) 0.01449(15) Uani 1 1 d . . .
C8 C 0.10830(5) 0.80231(9) 0.08882(3) 0.01319(14) Uani 1 1 d . . .
C9 C 0.18653(5) 0.83538(9) 0.13251(3) 0.01252(14) Uani 1 1 d . . .
C10 C 0.24396(6) 0.96253(9) 0.13129(3) 0.01419(15) Uani 1 1 d . . .
C11 C 0.32451(6) 0.97065(11) 0.12044(3) 0.01831(17) Uani 1 1 d . . .
H11A H 0.3528 0.8881 0.1142 0.022 Uiso 1 1 calc R . .
C12 C 0.36214(6) 1.10625(12) 0.11916(3) 0.02229(19) Uani 1 1 d . . .
H12A H 0.4158 1.1148 0.1116 0.027 Uiso 1 1 calc R . .
C13 C 0.31946(7) 1.22830(11) 0.12919(3) 0.02240(19) Uani 1 1 d . . .
H13A H 0.3456 1.3176 0.1282 0.027 Uiso 1 1 calc R . .
C14 C 0.23866(6) 1.22143(10) 0.14072(3) 0.01873(17) Uani 1 1 d . . .
H14A H 0.2111 1.3038 0.1476 0.022 Uiso 1 1 calc R . .
C15 C 0.20122(6) 1.08601(9) 0.14140(3) 0.01433(15) Uani 1 1 d . . .
C16 C 0.11178(5) 0.89295(9) 0.15237(3) 0.01246(14) Uani 1 1 d . . .
C17 C 0.22948(6) 0.69367(9) 0.19869(3) 0.01415(15) Uani 1 1 d . . .
C18 C 0.29504(6) 0.58638(11) 0.22294(3) 0.02038(17) Uani 1 1 d . . .
H18A H 0.3300 0.5368 0.2054 0.024 Uiso 1 1 calc R . .
H18B H 0.2800 0.5292 0.2467 0.024 Uiso 1 1 calc R . .
C19 C 0.31191(6) 0.74597(11) 0.23198(3) 0.02006(17) Uani 1 1 d . . .
H19A H 0.3066 0.7840 0.2610 0.024 Uiso 1 1 calc R . .
H19B H 0.3567 0.7915 0.2197 0.024 Uiso 1 1 calc R . .
C20 C 0.14136(6) 0.71033(9) 0.20788(3) 0.01384(14) Uani 1 1 d . . .
C21 C 0.07667(6) 0.58937(10) 0.20370(3) 0.01804(16) Uani 1 1 d . . .
H21A H 0.0957 0.4941 0.1974 0.022 Uiso 1 1 calc R . .
H21B H 0.0149 0.6101 0.1901 0.022 Uiso 1 1 calc R . .
C22 C 0.11926(6) 0.65570(10) 0.24980(3) 0.01841(16) Uani 1 1 d . . .
H22A H 0.0829 0.7158 0.2638 0.022 Uiso 1 1 calc R . .
H22B H 0.1636 0.5998 0.2711 0.022 Uiso 1 1 calc R . .
C23 C 0.14442(7) 0.88498(11) -0.02560(3) 0.02295(19) Uani 1 1 d . . .
C24 C 0.15356(8) 1.04445(12) -0.02846(4) 0.0266(2) Uani 1 1 d . . .
H24A H 0.1872 1.0670 -0.0500 0.040 Uiso 1 1 calc R . .
H24B H 0.1832 1.0815 0.0011 0.040 Uiso 1 1 calc R . .
H24C H 0.0961 1.0872 -0.0382 0.040 Uiso 1 1 calc R . .
C25 C 0.05547(6) 1.14478(10) 0.15574(3) 0.01741(16) Uani 1 1 d . . .
C26 C -0.02803(7) 1.08301(11) 0.16351(4) 0.0252(2) Uani 1 1 d . . .
H26A H -0.0764 1.1459 0.1506 0.038 Uiso 1 1 calc R . .
H26B H -0.0223 1.0732 0.1957 0.038 Uiso 1 1 calc R . .
H26C H -0.0388 0.9904 0.1492 0.038 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 0.0277(3) 0.0133(3) 0.0189(3) 0.0006(2) 0.0037(3) 0.0017(2)
O2 0.0732(7) 0.0328(5) 0.0258(4) -0.0042(3) 0.0280(4) -0.0058(5)
O3 0.0137(3) 0.0149(3) 0.0144(3) -0.0026(2) 0.0031(2) -0.0014(2)
O4 0.0356(4) 0.0115(3) 0.0372(4) -0.0001(3) 0.0158(3) 0.0019(3)
O5 0.0191(3) 0.0122(3) 0.0136(3) 0.0011(2) 0.0067(2) 0.0011(2)
O6 0.0177(3) 0.0134(3) 0.0128(3) 0.0012(2) 0.0041(2) 0.0030(2)
N1 0.0219(4) 0.0148(3) 0.0129(3) 0.0001(2) 0.0044(3) 0.0003(3)
N2 0.0166(3) 0.0093(3) 0.0164(3) -0.0006(2) 0.0051(3) -0.0009(2)
C1 0.0164(3) 0.0139(3) 0.0127(3) -0.0004(3) 0.0011(3) -0.0009(3)
C2 0.0184(4) 0.0142(3) 0.0147(3) -0.0016(3) 0.0024(3) 0.0007(3)
C3 0.0271(5) 0.0197(4) 0.0175(4) -0.0049(3) 0.0045(3) 0.0028(3)
C4 0.0283(5) 0.0156(4) 0.0230(4) -0.0061(3) 0.0018(4) 0.0032(3)
C5 0.0250(4) 0.0118(4) 0.0235(4) -0.0021(3) -0.0003(3) 0.0007(3)
C6 0.0210(4) 0.0125(3) 0.0179(4) -0.0005(3) 0.0016(3) -0.0008(3)
C7 0.0170(3) 0.0120(3) 0.0132(3) -0.0013(3) 0.0015(3) 0.0000(3)
C8 0.0145(3) 0.0118(3) 0.0129(3) -0.0008(3) 0.0028(3) -0.0004(3)
C9 0.0142(3) 0.0117(3) 0.0115(3) -0.0006(3) 0.0031(3) -0.0003(3)
C10 0.0156(3) 0.0146(3) 0.0119(3) -0.0002(3) 0.0026(3) -0.0025(3)
C11 0.0163(4) 0.0237(4) 0.0151(4) 0.0000(3) 0.0044(3) -0.0028(3)
C12 0.0184(4) 0.0298(5) 0.0185(4) 0.0020(4) 0.0044(3) -0.0087(4)
C13 0.0244(4) 0.0223(4) 0.0186(4) 0.0022(3) 0.0019(3) -0.0110(4)
C14 0.0230(4) 0.0145(4) 0.0169(4) 0.0011(3) 0.0018(3) -0.0052(3)
C15 0.0161(3) 0.0136(3) 0.0123(3) 0.0004(3) 0.0018(3) -0.0028(3)
C16 0.0141(3) 0.0104(3) 0.0127(3) -0.0005(3) 0.0033(3) -0.0006(3)
C17 0.0151(3) 0.0140(3) 0.0126(3) 0.0013(3) 0.0021(3) 0.0003(3)
C18 0.0188(4) 0.0197(4) 0.0212(4) 0.0049(3) 0.0027(3) 0.0043(3)
C19 0.0176(4) 0.0218(4) 0.0184(4) -0.0007(3) 0.0002(3) -0.0017(3)
C20 0.0161(3) 0.0120(3) 0.0134(3) 0.0015(3) 0.0037(3) 0.0001(3)
C21 0.0200(4) 0.0157(4) 0.0181(4) 0.0002(3) 0.0044(3) -0.0042(3)
C22 0.0221(4) 0.0197(4) 0.0139(4) 0.0028(3) 0.0054(3) -0.0020(3)
C23 0.0295(5) 0.0239(4) 0.0167(4) 0.0022(3) 0.0083(3) -0.0011(4)
C24 0.0308(5) 0.0241(5) 0.0267(5) 0.0085(4) 0.0104(4) 0.0004(4)
C25 0.0224(4) 0.0129(3) 0.0181(4) -0.0003(3) 0.0073(3) 0.0022(3)
C26 0.0220(4) 0.0190(4) 0.0383(6) 0.0006(4) 0.0145(4) 0.0030(3)

_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 C1 1.2062(11) . ?
O2 C23 1.2096(13) . ?
O3 C16 1.4443(10) . ?
O3 C8 1.4551(10) . ?
O4 C25 1.2192(11) . ?
O5 C16 1.3738(10) . ?
O5 C20 1.4399(10) . ?
O6 C9 1.4037(10) . ?
O6 C17 1.4255(10) . ?
N1 C23 1.4068(12) . ?
N1 C1 1.4071(11) . ?
N1 C2 1.4342(12) . ?
N2 C25 1.3800(11) . ?
N2 C15 1.4239(11) . ?
N2 C16 1.4577(11) . ?
C1 C8 1.5367(12) . ?
C2 C3 1.3868(13) . ?
C2 C7 1.3981(12) . ?
C3 C4 1.3940(14) . ?
C3 H3A 0.9300 . ?
C4 C5 1.3892(15) . ?
C4 H4A 0.9300 . ?
C5 C6 1.3954(13) . ?
C5 H5A 0.9300 . ?
C6 C7 1.3850(12) . ?
C6 H6A 0.9300 . ?
C7 C8 1.4853(11) . ?
C8 C9 1.5887(12) . ?
C9 C10 1.4927(12) . ?
C9 C16 1.5419(11) . ?
C10 C11 1.3849(12) . ?
C10 C15 1.4023(12) . ?
C11 C12 1.3975(14) . ?
C11 H11A 0.9300 . ?
C12 C13 1.3899(16) . ?
C12 H12A 0.9300 . ?
C13 C14 1.3979(14) . ?
C13 H13A 0.9300 . ?
C14 C15 1.3923(12) . ?
C14 H14A 0.9300 . ?
C17 C20 1.4846(12) . ?
C17 C18 1.4863(12) . ?
C17 C19 1.5040(13) . ?
C18 C19 1.5208(14) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C22 1.4858(12) . ?
C20 C21 1.4988(12) . ?
C21 C22 1.5160(13) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.4952(15) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.5016(14) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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 C8 92.05(6) . . ?
C16 O5 C20 113.29(6) . . ?
C9 O6 C17 112.19(6) . . ?
C23 N1 C1 126.05(8) . . ?
C23 N1 C2 125.09(8) . . ?
C1 N1 C2 108.84(7) . . ?
C25 N2 C15 125.43(7) . . ?
C25 N2 C16 124.80(7) . . ?
C15 N2 C16 109.50(7) . . ?
O1 C1 N1 126.95(8) . . ?
O1 C1 C8 126.36(8) . . ?
N1 C1 C8 106.67(7) . . ?
C3 C2 C7 121.16(9) . . ?
C3 C2 N1 129.05(9) . . ?
C7 C2 N1 109.73(7) . . ?
C2 C3 C4 117.37(9) . . ?
C2 C3 H3A 121.3 . . ?
C4 C3 H3A 121.3 . . ?
C5 C4 C3 122.09(9) . . ?
C5 C4 H4A 119.0 . . ?
C3 C4 H4A 119.0 . . ?
C4 C5 C6 119.91(9) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C7 C6 C5 118.61(9) . . ?
C7 C6 H6A 120.7 . . ?
C5 C6 H6A 120.7 . . ?
C6 C7 C2 120.84(8) . . ?
C6 C7 C8 130.42(8) . . ?
C2 C7 C8 108.72(7) . . ?
O3 C8 C7 118.58(7) . . ?
O3 C8 C1 112.83(7) . . ?
C7 C8 C1 103.04(7) . . ?
O3 C8 C9 90.06(6) . . ?
C7 C8 C9 118.78(7) . . ?
C1 C8 C9 113.96(7) . . ?
O6 C9 C10 118.49(7) . . ?
O6 C9 C16 116.30(7) . . ?
C10 C9 C16 104.89(7) . . ?
O6 C9 C8 110.05(7) . . ?
C10 C9 C8 118.45(7) . . ?
C16 C9 C8 83.58(6) . . ?
C11 C10 C15 121.45(8) . . ?
C11 C10 C9 129.86(8) . . ?
C15 C10 C9 108.63(7) . . ?
C10 C11 C12 118.19(9) . . ?
C10 C11 H11A 120.9 . . ?
C12 C11 H11A 120.9 . . ?
C13 C12 C11 120.11(9) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C12 C13 C14 122.26(9) . . ?
C12 C13 H13A 118.9 . . ?
C14 C13 H13A 118.9 . . ?
C15 C14 C13 117.21(9) . . ?
C15 C14 H14A 121.4 . . ?
C13 C14 H14A 121.4 . . ?
C14 C15 C10 120.78(8) . . ?
C14 C15 N2 128.71(8) . . ?
C10 C15 N2 110.51(7) . . ?
O5 C16 O3 114.16(7) . . ?
O5 C16 N2 109.22(7) . . ?
O3 C16 N2 114.42(7) . . ?
O5 C16 C9 120.82(7) . . ?
O3 C16 C9 92.35(6) . . ?
N2 C16 C9 105.01(6) . . ?
O6 C17 C20 112.51(7) . . ?
O6 C17 C18 113.30(7) . . ?
C20 C17 C18 122.54(7) . . ?
O6 C17 C19 116.73(7) . . ?
C20 C17 C19 121.57(8) . . ?
C18 C17 C19 61.14(6) . . ?
C17 C18 C19 60.01(6) . . ?
C17 C18 H18A 117.8 . . ?
C19 C18 H18A 117.8 . . ?
C17 C18 H18B 117.8 . . ?
C19 C18 H18B 117.8 . . ?
H18A C18 H18B 114.9 . . ?
C17 C19 C18 58.86(6) . . ?
C17 C19 H19A 117.9 . . ?
C18 C19 H19A 117.9 . . ?
C17 C19 H19B 117.9 . . ?
C18 C19 H19B 117.9 . . ?
H19A C19 H19B 115.0 . . ?
O5 C20 C17 111.57(7) . . ?
O5 C20 C22 112.40(7) . . ?
C17 C20 C22 123.57(8) . . ?
O5 C20 C21 116.38(7) . . ?
C17 C20 C21 123.21(8) . . ?
C22 C20 C21 61.05(6) . . ?
C20 C21 C22 59.05(6) . . ?
C20 C21 H21A 117.9 . . ?
C22 C21 H21A 117.9 . . ?
C20 C21 H21B 117.9 . . ?
C22 C21 H21B 117.9 . . ?
H21A C21 H21B 115.0 . . ?
C20 C22 C21 59.90(6) . . ?
C20 C22 H22A 117.8 . . ?
C21 C22 H22A 117.8 . . ?
C20 C22 H22B 117.8 . . ?
C21 C22 H22B 117.8 . . ?
H22A C22 H22B 114.9 . . ?
O2 C23 N1 119.53(10) . . ?
O2 C23 C24 122.43(10) . . ?
N1 C23 C24 118.02(9) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O4 C25 N2 121.18(9) . . ?
O4 C25 C26 121.65(9) . . ?
N2 C25 C26 117.17(8) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C23 N1 C1 O1 15.25(15) . . . . ?
C2 N1 C1 O1 -163.05(9) . . . . ?
C23 N1 C1 C8 -166.49(9) . . . . ?
C2 N1 C1 C8 15.21(9) . . . . ?
C23 N1 C2 C3 -7.97(16) . . . . ?
C1 N1 C2 C3 170.34(9) . . . . ?
C23 N1 C2 C7 174.81(9) . . . . ?
C1 N1 C2 C7 -6.87(10) . . . . ?
C7 C2 C3 C4 0.81(14) . . . . ?
N1 C2 C3 C4 -176.12(9) . . . . ?
C2 C3 C4 C5 0.14(15) . . . . ?
C3 C4 C5 C6 -1.12(16) . . . . ?
C4 C5 C6 C7 1.12(14) . . . . ?
C5 C6 C7 C2 -0.19(14) . . . . ?
C5 C6 C7 C8 -178.27(9) . . . . ?
C3 C2 C7 C6 -0.80(14) . . . . ?
N1 C2 C7 C6 176.67(8) . . . . ?
C3 C2 C7 C8 177.66(8) . . . . ?
N1 C2 C7 C8 -4.87(10) . . . . ?
C16 O3 C8 C7 134.07(8) . . . . ?
C16 O3 C8 C1 -105.39(7) . . . . ?
C16 O3 C8 C9 10.79(6) . . . . ?
C6 C7 C8 O3 -42.88(13) . . . . ?
C2 C7 C8 O3 138.85(8) . . . . ?
C6 C7 C8 C1 -168.31(9) . . . . ?
C2 C7 C8 C1 13.42(9) . . . . ?
C6 C7 C8 C9 64.61(12) . . . . ?
C2 C7 C8 C9 -113.66(8) . . . . ?
O1 C1 C8 O3 31.82(12) . . . . ?
N1 C1 C8 O3 -146.45(7) . . . . ?
O1 C1 C8 C7 160.89(9) . . . . ?
N1 C1 C8 C7 -17.38(9) . . . . ?
O1 C1 C8 C9 -69.03(11) . . . . ?
N1 C1 C8 C9 112.69(8) . . . . ?
C17 O6 C9 C10 93.13(8) . . . . ?
C17 O6 C9 C16 -33.33(10) . . . . ?
C17 O6 C9 C8 -126.06(7) . . . . ?
O3 C8 C9 O6 105.54(7) . . . . ?
C7 C8 C9 O6 -17.58(10) . . . . ?
C1 C8 C9 O6 -139.31(7) . . . . ?
O3 C8 C9 C10 -113.63(7) . . . . ?
C7 C8 C9 C10 123.25(8) . . . . ?
C1 C8 C9 C10 1.52(10) . . . . ?
O3 C8 C9 C16 -10.15(6) . . . . ?
C7 C8 C9 C16 -133.27(8) . . . . ?
C1 C8 C9 C16 105.00(7) . . . . ?
O6 C9 C10 C11 41.88(13) . . . . ?
C16 C9 C10 C11 173.62(9) . . . . ?
C8 C9 C10 C11 -95.66(11) . . . . ?
O6 C9 C10 C15 -140.96(7) . . . . ?
C16 C9 C10 C15 -9.21(9) . . . . ?
C8 C9 C10 C15 81.50(9) . . . . ?
C15 C10 C11 C12 -0.87(13) . . . . ?
C9 C10 C11 C12 175.98(9) . . . . ?
C10 C11 C12 C13 0.82(14) . . . . ?
C11 C12 C13 C14 -0.08(15) . . . . ?
C12 C13 C14 C15 -0.61(14) . . . . ?
C13 C14 C15 C10 0.57(13) . . . . ?
C13 C14 C15 N2 -179.55(8) . . . . ?
C11 C10 C15 C14 0.17(13) . . . . ?
C9 C10 C15 C14 -177.28(8) . . . . ?
C11 C10 C15 N2 -179.73(8) . . . . ?
C9 C10 C15 N2 2.82(9) . . . . ?
C25 N2 C15 C14 11.12(14) . . . . ?
C16 N2 C15 C14 -174.58(9) . . . . ?
C25 N2 C15 C10 -168.99(8) . . . . ?
C16 N2 C15 C10 5.31(10) . . . . ?
C20 O5 C16 O3 81.17(8) . . . . ?
C20 O5 C16 N2 -149.32(7) . . . . ?
C20 O5 C16 C9 -27.49(10) . . . . ?
C8 O3 C16 O5 -136.61(7) . . . . ?
C8 O3 C16 N2 96.53(7) . . . . ?
C8 O3 C16 C9 -11.13(6) . . . . ?
C25 N2 C16 O5 -65.47(10) . . . . ?
C15 N2 C16 O5 120.18(7) . . . . ?
C25 N2 C16 O3 63.90(11) . . . . ?
C15 N2 C16 O3 -110.45(8) . . . . ?
C25 N2 C16 C9 163.59(8) . . . . ?
C15 N2 C16 C9 -10.76(9) . . . . ?
O6 C9 C16 O5 21.12(11) . . . . ?
C10 C9 C16 O5 -111.87(8) . . . . ?
C8 C9 C16 O5 130.34(8) . . . . ?
O6 C9 C16 O3 -98.98(7) . . . . ?
C10 C9 C16 O3 128.03(6) . . . . ?
C8 C9 C16 O3 10.24(6) . . . . ?
O6 C9 C16 N2 144.95(7) . . . . ?
C10 C9 C16 N2 11.96(8) . . . . ?
C8 C9 C16 N2 -105.82(7) . . . . ?
C9 O6 C17 C20 54.40(9) . . . . ?
C9 O6 C17 C18 -161.27(7) . . . . ?
C9 O6 C17 C19 -93.08(9) . . . . ?
O6 C17 C18 C19 108.78(8) . . . . ?
C20 C17 C18 C19 -110.94(9) . . . . ?
O6 C17 C19 C18 -103.18(8) . . . . ?
C20 C17 C19 C18 112.47(9) . . . . ?
C16 O5 C20 C17 46.51(9) . . . . ?
C16 O5 C20 C22 -169.76(7) . . . . ?
C16 O5 C20 C21 -102.09(8) . . . . ?
O6 C17 C20 O5 -62.10(9) . . . . ?
C18 C17 C20 O5 157.34(8) . . . . ?
C19 C17 C20 O5 83.60(10) . . . . ?
O6 C17 C20 C22 158.93(8) . . . . ?
C18 C17 C20 C22 18.38(13) . . . . ?
C19 C17 C20 C22 -55.36(12) . . . . ?
O6 C17 C20 C21 83.99(10) . . . . ?
C18 C17 C20 C21 -56.57(12) . . . . ?
C19 C17 C20 C21 -130.31(9) . . . . ?
O5 C20 C21 C22 -102.23(8) . . . . ?
C17 C20 C21 C22 113.16(9) . . . . ?
O5 C20 C22 C21 108.74(8) . . . . ?
C17 C20 C22 C21 -112.59(9) . . . . ?
C1 N1 C23 O2 -175.63(11) . . . . ?
C2 N1 C23 O2 2.40(16) . . . . ?
C1 N1 C23 C24 6.38(15) . . . . ?
C2 N1 C23 C24 -175.60(9) . . . . ?
C15 N2 C25 O4 -4.15(14) . . . . ?
C16 N2 C25 O4 -177.61(9) . . . . ?
C15 N2 C25 C26 175.98(9) . . . . ?
C16 N2 C25 C26 2.53(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        32.69
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.058

# Attachment '- compound 4.cif'

data_wdd37a_0m
_database_code_depnum_ccdc_archive 'CCDC 838080'
#TrackingRef '- compound 4.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N O3'
_chemical_formula_sum            'C15 H15 N O3'
_chemical_formula_weight         257.28

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'

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

_cell_length_a                   5.1915(1)
_cell_length_b                   12.1482(3)
_cell_length_c                   20.3530(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.797(1)
_cell_angle_gamma                90.00
_cell_volume                     1282.98(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4986
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.52
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.248
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_max          0.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9598
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2009)'
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296
_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 SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14738
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         29.86
_reflns_number_total             3830
_reflns_number_gt                2921
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009)
;

_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^)+(0.0481P)^2^+0.0221P] 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         3830
_refine_ls_number_parameters     353
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0938
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_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
O1A O 0.7466(2) 0.58428(13) 0.04591(6) 0.0475(4) Uani 1 1 d . . .
O2A O 0.9211(2) 0.62076(13) -0.04730(7) 0.0496(3) Uani 1 1 d . . .
O3A O 0.4818(3) 0.57102(18) -0.26065(8) 0.0718(5) Uani 1 1 d . . .
N1A N 0.6739(3) 0.57230(17) -0.15904(8) 0.0507(4) Uani 1 1 d . . .
C1A C 0.5454(3) 0.50559(17) -0.05259(9) 0.0386(4) Uani 1 1 d . . .
C2A C 0.7473(3) 0.57367(17) -0.01957(9) 0.0396(4) Uani 1 1 d . . .
C3A C 0.5214(3) 0.54982(19) 0.08003(9) 0.0434(4) Uani 1 1 d . . .
C4A C 0.4351(3) 0.43956(18) 0.05834(9) 0.0439(4) Uani 1 1 d . . .
C5A C 0.3912(3) 0.43669(16) -0.01453(9) 0.0395(4) Uani 1 1 d . . .
C6A C 0.2058(4) 0.36994(18) -0.04502(11) 0.0476(5) Uani 1 1 d . . .
H6AA H 0.1051 0.3235 -0.0201 0.057 Uiso 1 1 calc R . .
C7A C 0.1723(4) 0.37324(19) -0.11270(11) 0.0512(5) Uani 1 1 d . . .
H7AA H 0.0464 0.3291 -0.1328 0.061 Uiso 1 1 calc R . .
C8A C 0.3196(4) 0.43989(19) -0.15121(10) 0.0486(5) Uani 1 1 d . . .
H8AA H 0.2916 0.4409 -0.1966 0.058 Uiso 1 1 calc R . .
C9A C 0.5114(3) 0.50607(17) -0.12201(9) 0.0416(4) Uani 1 1 d . . .
C10A C 0.6553(4) 0.59999(19) -0.22357(10) 0.0511(5) Uani 1 1 d . . .
C11A C 0.8738(5) 0.6704(2) -0.24564(12) 0.0640(6) Uani 1 1 d . . .
H11A H 0.8225 0.7085 -0.2852 0.096 Uiso 1 1 calc R . .
H11B H 1.0204 0.6248 -0.2538 0.096 Uiso 1 1 calc R . .
H11C H 0.9184 0.7230 -0.2120 0.096 Uiso 1 1 calc R . .
C12A C 0.3427(4) 0.6411(2) 0.09642(10) 0.0522(5) Uani 1 1 d . . .
H12A H 0.1606 0.6242 0.0985 0.063 Uiso 1 1 calc R . .
H12B H 0.3817 0.7142 0.0803 0.063 Uiso 1 1 calc R . .
C13A C 0.5224(4) 0.5922(2) 0.14842(10) 0.0551(6) Uani 1 1 d . . .
H13A H 0.6689 0.6360 0.1635 0.066 Uiso 1 1 calc R . .
H13B H 0.4478 0.5461 0.1818 0.066 Uiso 1 1 calc R . .
C14A C 0.5544(5) 0.3401(2) 0.09310(12) 0.0599(6) Uani 1 1 d . . .
H14A H 0.5883 0.2753 0.0669 0.072 Uiso 1 1 calc R . .
H14B H 0.6781 0.3535 0.1289 0.072 Uiso 1 1 calc R . .
C15A C 0.2795(4) 0.3702(2) 0.10340(11) 0.0589(6) Uani 1 1 d . . .
H15A H 0.2370 0.4013 0.1456 0.071 Uiso 1 1 calc R . .
H15B H 0.1473 0.3233 0.0836 0.071 Uiso 1 1 calc R . .
O1B O 0.6797(3) 0.77619(15) 0.47839(7) 0.0586(4) Uani 1 1 d . . .
O2B O 0.5232(3) 0.63811(15) 0.42190(7) 0.0626(4) Uani 1 1 d . . .
O3B O 1.0079(3) 0.45980(17) 0.25010(10) 0.0777(5) Uani 1 1 d . . .
N1B N 0.7710(3) 0.56327(17) 0.31890(8) 0.0497(4) Uani 1 1 d . . .
C1B C 0.8637(4) 0.73819(19) 0.37254(9) 0.0432(4) Uani 1 1 d . . .
C2B C 0.6788(4) 0.71270(19) 0.42418(9) 0.0463(5) Uani 1 1 d . . .
C3B C 0.8820(4) 0.8558(2) 0.48921(11) 0.0533(5) Uani 1 1 d . . .
C4B C 0.9375(4) 0.91690(19) 0.42827(11) 0.0520(5) Uani 1 1 d . . .
C5B C 0.9933(4) 0.83960(19) 0.37357(10) 0.0483(5) Uani 1 1 d . . .
C6B C 1.1657(5) 0.8638(2) 0.32491(12) 0.0616(6) Uani 1 1 d . . .
H6BA H 1.2532 0.9306 0.3256 0.074 Uiso 1 1 calc R . .
C7B C 1.2070(5) 0.7895(3) 0.27595(12) 0.0674(7) Uani 1 1 d . . .
H7BA H 1.3229 0.8069 0.2436 0.081 Uiso 1 1 calc R . .
C8B C 1.0816(4) 0.6896(2) 0.27320(10) 0.0569(6) Uani 1 1 d . . .
H8BA H 1.1131 0.6403 0.2394 0.068 Uiso 1 1 calc R . .
C9B C 0.9077(4) 0.66286(18) 0.32131(9) 0.0450(5) Uani 1 1 d . . .
C10B C 0.8243(4) 0.4699(2) 0.28528(10) 0.0513(5) Uani 1 1 d . . .
C11B C 0.6352(5) 0.3786(2) 0.29425(12) 0.0624(6) Uani 1 1 d . . .
H11D H 0.6448 0.3279 0.2583 0.094 Uiso 1 1 calc R . .
H11E H 0.4643 0.4086 0.2955 0.094 Uiso 1 1 calc R . .
H11F H 0.6752 0.3409 0.3347 0.094 Uiso 1 1 calc R . .
C12B C 1.0862(5) 0.8236(3) 0.53824(11) 0.0666(7) Uani 1 1 d . . .
H12C H 1.2586 0.8521 0.5326 0.080 Uiso 1 1 calc R . .
H12D H 1.0789 0.7501 0.5567 0.080 Uiso 1 1 calc R . .
C13B C 0.8780(5) 0.9040(3) 0.55575(12) 0.0715(7) Uani 1 1 d . . .
H13C H 0.7459 0.8789 0.5849 0.086 Uiso 1 1 calc R . .
H13D H 0.9255 0.9809 0.5607 0.086 Uiso 1 1 calc R . .
C14B C 0.7890(5) 1.0232(2) 0.41439(16) 0.0732(7) Uani 1 1 d . . .
H14C H 0.7406 1.0398 0.3691 0.088 Uiso 1 1 calc R . .
H14D H 0.6664 1.0470 0.4464 0.088 Uiso 1 1 calc R . .
C15B C 1.0687(5) 1.0267(2) 0.43380(15) 0.0719(7) Uani 1 1 d . . .
H15C H 1.1151 1.0533 0.4775 0.086 Uiso 1 1 calc R . .
H15D H 1.1892 1.0461 0.4002 0.086 Uiso 1 1 calc R . .
H1NA H 0.805(4) 0.601(2) -0.1350(12) 0.058(7) Uiso 1 1 d . . .
H1NB H 0.636(5) 0.562(2) 0.3471(13) 0.073(8) Uiso 1 1 d . . .

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
O1A 0.0377(6) 0.0596(10) 0.0451(7) -0.0074(7) 0.0008(5) -0.0078(6)
O2A 0.0435(7) 0.0500(9) 0.0552(8) -0.0003(7) 0.0035(6) -0.0073(7)
O3A 0.0708(10) 0.0931(14) 0.0512(9) 0.0039(9) -0.0052(7) 0.0000(10)
N1A 0.0514(9) 0.0558(12) 0.0447(9) -0.0015(9) 0.0016(7) -0.0051(8)
C1A 0.0357(8) 0.0355(10) 0.0445(10) -0.0033(8) -0.0005(7) 0.0031(7)
C2A 0.0347(8) 0.0359(10) 0.0480(10) -0.0032(9) -0.0007(7) 0.0039(7)
C3A 0.0350(8) 0.0520(12) 0.0430(10) -0.0043(9) -0.0003(7) -0.0015(8)
C4A 0.0395(9) 0.0434(12) 0.0491(11) 0.0005(9) 0.0024(8) 0.0016(8)
C5A 0.0367(8) 0.0334(10) 0.0484(10) -0.0022(8) 0.0012(7) 0.0033(7)
C6A 0.0458(10) 0.0380(11) 0.0588(12) -0.0039(10) -0.0010(8) -0.0042(9)
C7A 0.0517(10) 0.0406(12) 0.0606(12) -0.0089(10) -0.0092(9) -0.0040(9)
C8A 0.0513(10) 0.0461(12) 0.0480(11) -0.0088(10) -0.0059(8) 0.0033(10)
C9A 0.0415(9) 0.0362(10) 0.0469(10) -0.0037(9) 0.0005(7) 0.0057(8)
C10A 0.0552(11) 0.0495(13) 0.0491(11) -0.0027(10) 0.0080(9) 0.0155(10)
C11A 0.0709(14) 0.0636(16) 0.0585(13) 0.0062(12) 0.0178(11) 0.0062(12)
C12A 0.0414(9) 0.0545(14) 0.0604(12) -0.0141(11) -0.0027(8) 0.0004(9)
C13A 0.0481(10) 0.0704(16) 0.0466(11) -0.0098(11) -0.0018(8) -0.0073(10)
C14A 0.0690(13) 0.0530(14) 0.0577(13) 0.0079(11) 0.0016(10) 0.0079(12)
C15A 0.0655(13) 0.0573(15) 0.0547(12) -0.0007(11) 0.0152(10) -0.0112(12)
O1B 0.0619(8) 0.0678(11) 0.0469(8) -0.0156(7) 0.0122(7) -0.0100(8)
O2B 0.0653(9) 0.0676(12) 0.0560(9) -0.0120(8) 0.0183(7) -0.0213(9)
O3B 0.0754(11) 0.0688(12) 0.0904(12) -0.0161(10) 0.0298(10) 0.0086(10)
N1B 0.0504(9) 0.0562(12) 0.0429(9) -0.0083(9) 0.0081(7) -0.0032(8)
C1B 0.0422(9) 0.0490(12) 0.0384(9) 0.0002(9) -0.0001(7) -0.0010(9)
C2B 0.0479(10) 0.0505(13) 0.0405(10) -0.0046(9) 0.0033(8) -0.0010(9)
C3B 0.0541(11) 0.0556(14) 0.0499(11) -0.0135(10) -0.0011(9) 0.0013(10)
C4B 0.0550(11) 0.0460(13) 0.0544(12) -0.0048(10) -0.0085(9) -0.0015(10)
C5B 0.0498(10) 0.0495(13) 0.0454(11) 0.0034(9) -0.0026(8) -0.0031(9)
C6B 0.0673(13) 0.0586(15) 0.0593(13) 0.0072(12) 0.0074(11) -0.0165(12)
C7B 0.0698(14) 0.0791(19) 0.0543(13) 0.0078(13) 0.0167(11) -0.0161(14)
C8B 0.0596(12) 0.0693(17) 0.0423(11) -0.0039(11) 0.0098(9) -0.0043(11)
C9B 0.0452(9) 0.0503(12) 0.0393(10) -0.0018(9) 0.0016(7) -0.0004(9)
C10B 0.0553(11) 0.0551(14) 0.0432(10) -0.0062(10) -0.0008(9) 0.0051(10)
C11B 0.0714(14) 0.0568(15) 0.0590(13) -0.0098(12) 0.0022(11) -0.0037(12)
C12B 0.0684(14) 0.0747(18) 0.0562(13) -0.0050(13) -0.0076(11) 0.0043(13)
C13B 0.0792(15) 0.0787(19) 0.0566(14) -0.0263(13) 0.0007(12) 0.0004(15)
C14B 0.0798(16) 0.0543(16) 0.0842(18) -0.0043(14) -0.0157(13) 0.0075(13)
C15B 0.0806(16) 0.0547(16) 0.0794(17) -0.0098(14) -0.0131(13) -0.0133(13)

_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
O1A C2A 1.339(2) . ?
O1A C3A 1.440(2) . ?
O2A C2A 1.221(2) . ?
O3A C10A 1.209(3) . ?
N1A C10A 1.356(3) . ?
N1A C9A 1.402(3) . ?
N1A H1NA 0.90(2) . ?
C1A C5A 1.407(3) . ?
C1A C9A 1.418(3) . ?
C1A C2A 1.480(3) . ?
C3A C4A 1.476(3) . ?
C3A C13A 1.484(3) . ?
C3A C12A 1.490(3) . ?
C4A C5A 1.494(3) . ?
C4A C15A 1.500(3) . ?
C4A C14A 1.522(3) . ?
C5A C6A 1.390(3) . ?
C6A C7A 1.384(3) . ?
C6A H6AA 0.9300 . ?
C7A C8A 1.376(3) . ?
C7A H7AA 0.9300 . ?
C8A C9A 1.398(3) . ?
C8A H8AA 0.9300 . ?
C10A C11A 1.501(3) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C12A C13A 1.510(3) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C14A C15A 1.494(3) . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
O1B C2B 1.346(2) . ?
O1B C3B 1.439(3) . ?
O2B C2B 1.214(2) . ?
O3B C10B 1.216(3) . ?
N1B C10B 1.358(3) . ?
N1B C9B 1.403(3) . ?
N1B H1NB 0.92(3) . ?
C1B C5B 1.404(3) . ?
C1B C9B 1.411(3) . ?
C1B C2B 1.478(3) . ?
C3B C13B 1.476(3) . ?
C3B C4B 1.481(3) . ?
C3B C12B 1.486(3) . ?
C4B C5B 1.492(3) . ?
C4B C15B 1.501(3) . ?
C4B C14B 1.526(4) . ?
C5B C6B 1.387(3) . ?
C6B C7B 1.366(4) . ?
C6B H6BA 0.9300 . ?
C7B C8B 1.378(4) . ?
C7B H7BA 0.9300 . ?
C8B C9B 1.391(3) . ?
C8B H8BA 0.9300 . ?
C10B C11B 1.495(3) . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12B C13B 1.508(4) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C14B C15B 1.493(4) . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?

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
C2A O1A C3A 118.66(14) . . ?
C10A N1A C9A 129.58(19) . . ?
C10A N1A H1NA 117.4(16) . . ?
C9A N1A H1NA 113.0(16) . . ?
C5A C1A C9A 119.71(16) . . ?
C5A C1A C2A 119.30(16) . . ?
C9A C1A C2A 120.95(17) . . ?
O2A C2A O1A 116.11(16) . . ?
O2A C2A C1A 125.09(17) . . ?
O1A C2A C1A 118.79(16) . . ?
O1A C3A C4A 111.28(16) . . ?
O1A C3A C13A 111.87(16) . . ?
C4A C3A C13A 125.99(19) . . ?
O1A C3A C12A 114.32(18) . . ?
C4A C3A C12A 123.86(16) . . ?
C13A C3A C12A 61.04(15) . . ?
C3A C4A C5A 110.71(17) . . ?
C3A C4A C15A 119.43(18) . . ?
C5A C4A C15A 121.70(18) . . ?
C3A C4A C14A 117.80(16) . . ?
C5A C4A C14A 119.35(19) . . ?
C15A C4A C14A 59.26(15) . . ?
C6A C5A C1A 119.95(17) . . ?
C6A C5A C4A 122.60(17) . . ?
C1A C5A C4A 117.45(16) . . ?
C7A C6A C5A 119.42(19) . . ?
C7A C6A H6AA 120.3 . . ?
C5A C6A H6AA 120.3 . . ?
C8A C7A C6A 121.97(19) . . ?
C8A C7A H7AA 119.0 . . ?
C6A C7A H7AA 119.0 . . ?
C7A C8A C9A 119.85(18) . . ?
C7A C8A H8AA 120.1 . . ?
C9A C8A H8AA 120.1 . . ?
C8A C9A N1A 122.27(17) . . ?
C8A C9A C1A 119.07(18) . . ?
N1A C9A C1A 118.66(17) . . ?
O3A C10A N1A 124.1(2) . . ?
O3A C10A C11A 122.3(2) . . ?
N1A C10A C11A 113.6(2) . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C3A C12A C13A 59.27(14) . . ?
C3A C12A H12A 117.8 . . ?
C13A C12A H12A 117.8 . . ?
C3A C12A H12B 117.8 . . ?
C13A C12A H12B 117.8 . . ?
H12A C12A H12B 115.0 . . ?
C3A C13A C12A 59.70(14) . . ?
C3A C13A H13A 117.8 . . ?
C12A C13A H13A 117.8 . . ?
C3A C13A H13B 117.8 . . ?
C12A C13A H13B 117.8 . . ?
H13A C13A H13B 114.9 . . ?
C15A C14A C4A 59.64(15) . . ?
C15A C14A H14A 117.8 . . ?
C4A C14A H14A 117.8 . . ?
C15A C14A H14B 117.8 . . ?
C4A C14A H14B 117.8 . . ?
H14A C14A H14B 114.9 . . ?
C14A C15A C4A 61.10(14) . . ?
C14A C15A H15A 117.7 . . ?
C4A C15A H15A 117.7 . . ?
C14A C15A H15B 117.7 . . ?
C4A C15A H15B 117.7 . . ?
H15A C15A H15B 114.8 . . ?
C2B O1B C3B 119.62(15) . . ?
C10B N1B C9B 128.86(17) . . ?
C10B N1B H1NB 118.4(19) . . ?
C9B N1B H1NB 112.5(19) . . ?
C5B C1B C9B 119.43(17) . . ?
C5B C1B C2B 119.67(18) . . ?
C9B C1B C2B 120.89(19) . . ?
O2B C2B O1B 116.37(17) . . ?
O2B C2B C1B 125.13(18) . . ?
O1B C2B C1B 118.50(18) . . ?
O1B C3B C13B 112.1(2) . . ?
O1B C3B C4B 111.64(17) . . ?
C13B C3B C4B 125.3(2) . . ?
O1B C3B C12B 115.3(2) . . ?
C13B C3B C12B 61.21(17) . . ?
C4B C3B C12B 122.7(2) . . ?
C3B C4B C5B 110.92(19) . . ?
C3B C4B C15B 118.85(19) . . ?
C5B C4B C15B 121.2(2) . . ?
C3B C4B C14B 117.9(2) . . ?
C5B C4B C14B 120.2(2) . . ?
C15B C4B C14B 59.12(17) . . ?
C6B C5B C1B 119.7(2) . . ?
C6B C5B C4B 123.0(2) . . ?
C1B C5B C4B 117.34(18) . . ?
C7B C6B C5B 120.0(2) . . ?
C7B C6B H6BA 120.0 . . ?
C5B C6B H6BA 120.0 . . ?
C6B C7B C8B 121.8(2) . . ?
C6B C7B H7BA 119.1 . . ?
C8B C7B H7BA 119.1 . . ?
C7B C8B C9B 119.6(2) . . ?
C7B C8B H8BA 120.2 . . ?
C9B C8B H8BA 120.2 . . ?
C8B C9B N1B 121.04(19) . . ?
C8B C9B C1B 119.5(2) . . ?
N1B C9B C1B 119.44(17) . . ?
O3B C10B N1B 123.8(2) . . ?
O3B C10B C11B 121.8(2) . . ?
N1B C10B C11B 114.37(18) . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C3B C12B C13B 59.09(15) . . ?
C3B C12B H12C 117.9 . . ?
C13B C12B H12C 117.9 . . ?
C3B C12B H12D 117.9 . . ?
C13B C12B H12D 117.9 . . ?
H12C C12B H12D 115.0 . . ?
C3B C13B C12B 59.70(15) . . ?
C3B C13B H13C 117.8 . . ?
C12B C13B H13C 117.8 . . ?
C3B C13B H13D 117.8 . . ?
C12B C13B H13D 117.8 . . ?
H13C C13B H13D 114.9 . . ?
C15B C14B C4B 59.61(17) . . ?
C15B C14B H14C 117.8 . . ?
C4B C14B H14C 117.8 . . ?
C15B C14B H14D 117.8 . . ?
C4B C14B H14D 117.8 . . ?
H14C C14B H14D 114.9 . . ?
C14B C15B C4B 61.27(17) . . ?
C14B C15B H15C 117.6 . . ?
C4B C15B H15C 117.6 . . ?
C14B C15B H15D 117.6 . . ?
C4B C15B H15D 117.6 . . ?
H15C C15B H15D 114.7 . . ?

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
C3A O1A C2A O2A 167.84(18) . . . . ?
C3A O1A C2A C1A -13.3(3) . . . . ?
C5A C1A C2A O2A 166.14(18) . . . . ?
C9A C1A C2A O2A -11.7(3) . . . . ?
C5A C1A C2A O1A -12.6(3) . . . . ?
C9A C1A C2A O1A 169.56(17) . . . . ?
C2A O1A C3A C4A 47.8(2) . . . . ?
C2A O1A C3A C13A -165.46(19) . . . . ?
C2A O1A C3A C12A -98.5(2) . . . . ?
O1A C3A C4A C5A -55.04(19) . . . . ?
C13A C3A C4A C5A 163.98(17) . . . . ?
C12A C3A C4A C5A 87.5(2) . . . . ?
O1A C3A C4A C15A 155.84(17) . . . . ?
C13A C3A C4A C15A 14.9(3) . . . . ?
C12A C3A C4A C15A -61.6(3) . . . . ?
O1A C3A C4A C14A 87.3(2) . . . . ?
C13A C3A C4A C14A -53.7(3) . . . . ?
C12A C3A C4A C14A -130.2(2) . . . . ?
C9A C1A C5A C6A -0.3(3) . . . . ?
C2A C1A C5A C6A -178.17(18) . . . . ?
C9A C1A C5A C4A -179.95(17) . . . . ?
C2A C1A C5A C4A 2.2(2) . . . . ?
C3A C4A C5A C6A -148.54(17) . . . . ?
C15A C4A C5A C6A -0.2(3) . . . . ?
C14A C4A C5A C6A 69.8(2) . . . . ?
C3A C4A C5A C1A 31.1(2) . . . . ?
C15A C4A C5A C1A 179.41(18) . . . . ?
C14A C4A C5A C1A -110.6(2) . . . . ?
C1A C5A C6A C7A -0.9(3) . . . . ?
C4A C5A C6A C7A 178.68(19) . . . . ?
C5A C6A C7A C8A 0.8(3) . . . . ?
C6A C7A C8A C9A 0.6(3) . . . . ?
C7A C8A C9A N1A 177.45(19) . . . . ?
C7A C8A C9A C1A -1.9(3) . . . . ?
C10A N1A C9A C8A 12.1(3) . . . . ?
C10A N1A C9A C1A -168.6(2) . . . . ?
C5A C1A C9A C8A 1.7(3) . . . . ?
C2A C1A C9A C8A 179.54(18) . . . . ?
C5A C1A C9A N1A -177.63(17) . . . . ?
C2A C1A C9A N1A 0.2(3) . . . . ?
C9A N1A C10A O3A 1.4(4) . . . . ?
C9A N1A C10A C11A -178.2(2) . . . . ?
O1A C3A C12A C13A -102.54(18) . . . . ?
C4A C3A C12A C13A 115.9(2) . . . . ?
O1A C3A C13A C12A 106.6(2) . . . . ?
C4A C3A C13A C12A -112.7(2) . . . . ?
C3A C4A C14A C15A 109.4(2) . . . . ?
C5A C4A C14A C15A -111.5(2) . . . . ?
C3A C4A C15A C14A -106.7(2) . . . . ?
C5A C4A C15A C14A 107.6(2) . . . . ?
C3B O1B C2B O2B 171.0(2) . . . . ?
C3B O1B C2B C1B -9.0(3) . . . . ?
C5B C1B C2B O2B 165.9(2) . . . . ?
C9B C1B C2B O2B -12.8(3) . . . . ?
C5B C1B C2B O1B -14.1(3) . . . . ?
C9B C1B C2B O1B 167.27(18) . . . . ?
C2B O1B C3B C13B -170.2(2) . . . . ?
C2B O1B C3B C4B 43.5(3) . . . . ?
C2B O1B C3B C12B -102.7(2) . . . . ?
O1B C3B C4B C5B -53.9(2) . . . . ?
C13B C3B C4B C5B 165.1(2) . . . . ?
C12B C3B C4B C5B 89.4(3) . . . . ?
O1B C3B C4B C15B 158.6(2) . . . . ?
C13B C3B C4B C15B 17.7(3) . . . . ?
C12B C3B C4B C15B -58.1(3) . . . . ?
O1B C3B C4B C14B 90.4(2) . . . . ?
C13B C3B C4B C14B -50.6(3) . . . . ?
C12B C3B C4B C14B -126.3(2) . . . . ?
C9B C1B C5B C6B -1.0(3) . . . . ?
C2B C1B C5B C6B -179.64(19) . . . . ?
C9B C1B C5B C4B 179.24(18) . . . . ?
C2B C1B C5B C4B 0.6(3) . . . . ?
C3B C4B C5B C6B -146.9(2) . . . . ?
C15B C4B C5B C6B -0.3(3) . . . . ?
C14B C4B C5B C6B 69.7(3) . . . . ?
C3B C4B C5B C1B 32.8(3) . . . . ?
C15B C4B C5B C1B 179.4(2) . . . . ?
C14B C4B C5B C1B -110.6(2) . . . . ?
C1B C5B C6B C7B 0.6(3) . . . . ?
C4B C5B C6B C7B -179.7(2) . . . . ?
C5B C6B C7B C8B -0.1(4) . . . . ?
C6B C7B C8B C9B 0.1(4) . . . . ?
C7B C8B C9B N1B 178.1(2) . . . . ?
C7B C8B C9B C1B -0.5(3) . . . . ?
C10B N1B C9B C8B 19.2(3) . . . . ?
C10B N1B C9B C1B -162.3(2) . . . . ?
C5B C1B C9B C8B 0.9(3) . . . . ?
C2B C1B C9B C8B 179.57(19) . . . . ?
C5B C1B C9B N1B -177.63(18) . . . . ?
C2B C1B C9B N1B 1.0(3) . . . . ?
C9B N1B C10B O3B -0.7(4) . . . . ?
C9B N1B C10B C11B 179.91(19) . . . . ?
O1B C3B C12B C13B -102.4(2) . . . . ?
C4B C3B C12B C13B 115.5(3) . . . . ?
O1B C3B C13B C12B 107.7(2) . . . . ?
C4B C3B C13B C12B -111.5(3) . . . . ?
C3B C4B C14B C15B 108.6(2) . . . . ?
C5B C4B C14B C15B -110.4(2) . . . . ?
C3B C4B C15B C14B -107.1(2) . . . . ?
C5B C4B C15B C14B 108.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        29.86
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.028
# Attachment '- compound 26.cif'

data_wdd23_0m
_database_code_depnum_ccdc_archive 'CCDC 838081'
#TrackingRef '- compound 26.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 N O4'
_chemical_formula_sum            'C16 H15 N O4'
_chemical_formula_weight         285.29

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_Hall  '-P 2ybc'
_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                   9.2089(2)
_cell_length_b                   15.1611(4)
_cell_length_c                   12.0162(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.926(1)
_cell_angle_gamma                90.00
_cell_volume                     1375.51(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      35.09

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.267
_exptl_crystal_size_mid          0.573
_exptl_crystal_size_max          0.739
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9299
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2009)'
_exptl_special_details           
;
The crystal was placed in the cold stream of an Oxford Cryosystems
Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating
at 100.0(1)K.
;
_diffrn_ambient_temperature      100.0(1)
_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 SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23386
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         35.10
_reflns_number_total             6088
_reflns_number_gt                5091
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009)
;

_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^)+(0.0689P)^2^+0.3013P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6088
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1286
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_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 0.76672(8) 0.43137(4) 0.41075(6) 0.01900(12) Uani 1 1 d . . .
O2 O 0.58948(8) 0.49049(4) 0.19839(6) 0.01707(11) Uani 1 1 d . . .
O3 O 0.86273(11) 0.72297(4) 0.37128(8) 0.02939(16) Uani 1 1 d . . .
O4 O 0.91656(10) 0.38433(4) 0.28371(8) 0.02685(15) Uani 1 1 d . . .
N1 N 0.79629(9) 0.57986(5) 0.37812(7) 0.01750(12) Uani 1 1 d . . .
C1 C 0.86882(11) 0.64546(5) 0.34542(8) 0.01810(14) Uani 1 1 d . . .
C2 C 0.95938(10) 0.61927(5) 0.27999(7) 0.01595(13) Uani 1 1 d . . .
C3 C 1.03047(12) 0.68528(6) 0.24426(9) 0.02229(16) Uani 1 1 d . . .
H3A H 1.0175 0.7442 0.2586 0.027 Uiso 1 1 calc R . .
C4 C 1.12074(13) 0.66314(7) 0.18712(10) 0.02823(19) Uani 1 1 d . . .
H4A H 1.1663 0.7075 0.1619 0.034 Uiso 1 1 calc R . .
C5 C 1.14354(13) 0.57520(7) 0.16723(10) 0.02770(19) Uani 1 1 d . . .
H5A H 1.2069 0.5609 0.1312 0.033 Uiso 1 1 calc R . .
C6 C 1.07159(11) 0.50888(6) 0.20130(9) 0.02162(15) Uani 1 1 d . . .
H6A H 1.0857 0.4500 0.1875 0.026 Uiso 1 1 calc R . .
C7 C 0.97771(10) 0.53126(5) 0.25651(7) 0.01567(13) Uani 1 1 d . . .
C8 C 0.89508(10) 0.46278(5) 0.28895(8) 0.01669(13) Uani 1 1 d . . .
C9 C 0.76307(10) 0.49289(5) 0.32173(7) 0.01508(13) Uani 1 1 d . . .
C10 C 0.52471(10) 0.40387(5) 0.19111(8) 0.01658(13) Uani 1 1 d . . .
C11 C 0.60805(10) 0.38020(5) 0.33650(7) 0.01588(13) Uani 1 1 d . . .
C12 C 0.50048(13) 0.34319(6) 0.08359(9) 0.02321(16) Uani 1 1 d . . .
H12A H 0.5258 0.2811 0.1056 0.028 Uiso 1 1 calc R . .
H12B H 0.5276 0.3657 0.0219 0.028 Uiso 1 1 calc R . .
C13 C 0.34221(12) 0.38225(6) 0.07505(9) 0.02398(16) Uani 1 1 d . . .
H13A H 0.2748 0.4279 0.0079 0.029 Uiso 1 1 calc R . .
H13B H 0.2729 0.3433 0.0916 0.029 Uiso 1 1 calc R . .
C14 C 0.61002(12) 0.29151(6) 0.38942(9) 0.02147(15) Uani 1 1 d . . .
H14A H 0.7195 0.2717 0.4715 0.026 Uiso 1 1 calc R . .
H14B H 0.5403 0.2454 0.3240 0.026 Uiso 1 1 calc R . .
C15 C 0.51127(12) 0.36739(7) 0.40138(9) 0.02404(17) Uani 1 1 d . . .
H15A H 0.3829 0.3665 0.3429 0.029 Uiso 1 1 calc R . .
H15B H 0.5622 0.3929 0.4905 0.029 Uiso 1 1 calc R . .
C16 C 0.69335(12) 0.60700(6) 0.43060(10) 0.02405(17) Uani 1 1 d . . .
H16A H 0.7487 0.6572 0.4890 0.036 Uiso 1 1 calc R . .
H16B H 0.6886 0.5593 0.4810 0.036 Uiso 1 1 calc R . .
H16C H 0.5753 0.6223 0.3562 0.036 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 0.0170(3) 0.0215(3) 0.0140(2) 0.00274(19) 0.0062(2) -0.0036(2)
O2 0.0159(2) 0.0169(2) 0.0140(2) 0.00165(18) 0.0059(2) -0.00098(19)
O3 0.0402(4) 0.0148(3) 0.0380(4) -0.0050(2) 0.0252(3) 0.0008(3)
O4 0.0326(4) 0.0140(3) 0.0395(4) -0.0012(2) 0.0239(3) 0.0022(2)
N1 0.0181(3) 0.0167(3) 0.0203(3) -0.0040(2) 0.0126(3) -0.0011(2)
C1 0.0193(3) 0.0146(3) 0.0191(3) -0.0016(2) 0.0101(3) 0.0003(2)
C2 0.0163(3) 0.0147(3) 0.0147(3) -0.0001(2) 0.0076(3) -0.0012(2)
C3 0.0230(4) 0.0199(4) 0.0206(3) 0.0012(3) 0.0105(3) -0.0062(3)
C4 0.0249(4) 0.0362(5) 0.0237(4) 0.0017(3) 0.0140(4) -0.0098(4)
C5 0.0220(4) 0.0415(5) 0.0237(4) -0.0010(3) 0.0155(3) -0.0035(4)
C6 0.0188(3) 0.0275(4) 0.0197(3) -0.0015(3) 0.0117(3) 0.0017(3)
C7 0.0154(3) 0.0162(3) 0.0146(3) -0.0001(2) 0.0080(3) 0.0004(2)
C8 0.0177(3) 0.0143(3) 0.0178(3) -0.0010(2) 0.0100(3) 0.0003(2)
C9 0.0152(3) 0.0150(3) 0.0141(3) 0.0003(2) 0.0078(3) -0.0008(2)
C10 0.0168(3) 0.0175(3) 0.0141(3) 0.0004(2) 0.0081(3) -0.0023(2)
C11 0.0148(3) 0.0189(3) 0.0143(3) 0.0008(2) 0.0085(3) -0.0015(2)
C12 0.0294(4) 0.0225(4) 0.0185(3) -0.0040(3) 0.0141(3) -0.0055(3)
C13 0.0195(4) 0.0274(4) 0.0171(3) -0.0003(3) 0.0059(3) -0.0051(3)
C14 0.0230(4) 0.0215(4) 0.0206(3) 0.0039(3) 0.0129(3) -0.0016(3)
C15 0.0221(4) 0.0338(4) 0.0220(4) 0.0026(3) 0.0160(3) 0.0004(3)
C16 0.0227(4) 0.0286(4) 0.0258(4) -0.0033(3) 0.0169(3) 0.0033(3)

_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 C9 1.4051(9) . ?
O1 C11 1.4283(10) . ?
O2 C10 1.4242(9) . ?
O2 C9 1.4285(9) . ?
O3 C1 1.2250(10) . ?
O4 C8 1.2133(10) . ?
N1 C1 1.3748(10) . ?
N1 C9 1.4331(10) . ?
N1 C16 1.4664(10) . ?
C1 C2 1.4906(11) . ?
C2 C3 1.3916(11) . ?
C2 C7 1.3939(11) . ?
C3 C4 1.3888(13) . ?
C3 H3A 0.9300 . ?
C4 C5 1.3915(16) . ?
C4 H4A 0.9300 . ?
C5 C6 1.3886(13) . ?
C5 H5A 0.9300 . ?
C6 C7 1.3997(11) . ?
C6 H6A 0.9300 . ?
C7 C8 1.4658(11) . ?
C8 C9 1.5459(10) . ?
C10 C13 1.4809(12) . ?
C10 C11 1.4949(10) . ?
C10 C12 1.4951(11) . ?
C11 C14 1.4830(11) . ?
C11 C15 1.4951(11) . ?
C12 C13 1.5213(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.5234(13) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C9 O1 C11 108.36(6) . . ?
C10 O2 C9 105.53(6) . . ?
C1 N1 C9 122.52(6) . . ?
C1 N1 C16 117.34(7) . . ?
C9 N1 C16 116.48(7) . . ?
O3 C1 N1 121.42(8) . . ?
O3 C1 C2 120.66(8) . . ?
N1 C1 C2 117.90(7) . . ?
C3 C2 C7 119.54(7) . . ?
C3 C2 C1 118.37(7) . . ?
C7 C2 C1 122.07(7) . . ?
C4 C3 C2 119.95(8) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 120.56(8) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C6 C5 C4 119.92(8) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C7 119.52(8) . . ?
C5 C6 H6A 120.2 . . ?
C7 C6 H6A 120.2 . . ?
C2 C7 C6 120.48(7) . . ?
C2 C7 C8 118.86(7) . . ?
C6 C7 C8 120.66(7) . . ?
O4 C8 C7 123.76(7) . . ?
O4 C8 C9 118.56(7) . . ?
C7 C8 C9 117.54(6) . . ?
O1 C9 O2 107.32(6) . . ?
O1 C9 N1 110.20(6) . . ?
O2 C9 N1 108.86(6) . . ?
O1 C9 C8 108.56(6) . . ?
O2 C9 C8 107.71(6) . . ?
N1 C9 C8 113.95(6) . . ?
O2 C10 C13 118.13(7) . . ?
O2 C10 C11 103.46(6) . . ?
C13 C10 C11 126.44(7) . . ?
O2 C10 C12 118.07(6) . . ?
C13 C10 C12 61.48(6) . . ?
C11 C10 C12 125.80(7) . . ?
O1 C11 C14 117.88(7) . . ?
O1 C11 C10 104.88(6) . . ?
C14 C11 C10 126.21(7) . . ?
O1 C11 C15 116.55(7) . . ?
C14 C11 C15 61.53(6) . . ?
C10 C11 C15 125.46(7) . . ?
C10 C12 C13 58.80(6) . . ?
C10 C12 H12A 117.9 . . ?
C13 C12 H12A 117.9 . . ?
C10 C12 H12B 117.9 . . ?
C13 C12 H12B 117.9 . . ?
H12A C12 H12B 115.0 . . ?
C10 C13 C12 59.72(6) . . ?
C10 C13 H13A 117.8 . . ?
C12 C13 H13A 117.8 . . ?
C10 C13 H13B 117.8 . . ?
C12 C13 H13B 117.8 . . ?
H13A C13 H13B 114.9 . . ?
C11 C14 C15 59.63(5) . . ?
C11 C14 H14A 117.8 . . ?
C15 C14 H14A 117.8 . . ?
C11 C14 H14B 117.8 . . ?
C15 C14 H14B 117.8 . . ?
H14A C14 H14B 114.9 . . ?
C11 C15 C14 58.84(5) . . ?
C11 C15 H15A 117.9 . . ?
C14 C15 H15A 117.9 . . ?
C11 C15 H15B 117.9 . . ?
C14 C15 H15B 117.9 . . ?
H15A C15 H15B 115.0 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C9 N1 C1 O3 164.65(8) . . . . ?
C16 N1 C1 O3 6.97(12) . . . . ?
C9 N1 C1 C2 -16.73(11) . . . . ?
C16 N1 C1 C2 -174.41(7) . . . . ?
O3 C1 C2 C3 -2.50(12) . . . . ?
N1 C1 C2 C3 178.87(7) . . . . ?
O3 C1 C2 C7 176.15(8) . . . . ?
N1 C1 C2 C7 -2.48(12) . . . . ?
C7 C2 C3 C4 -0.76(13) . . . . ?
C1 C2 C3 C4 177.93(8) . . . . ?
C2 C3 C4 C5 -1.09(14) . . . . ?
C3 C4 C5 C6 1.73(15) . . . . ?
C4 C5 C6 C7 -0.50(14) . . . . ?
C3 C2 C7 C6 1.98(12) . . . . ?
C1 C2 C7 C6 -176.66(7) . . . . ?
C3 C2 C7 C8 -177.22(7) . . . . ?
C1 C2 C7 C8 4.14(11) . . . . ?
C5 C6 C7 C2 -1.35(12) . . . . ?
C5 C6 C7 C8 177.84(8) . . . . ?
C2 C7 C8 O4 -173.14(8) . . . . ?
C6 C7 C8 O4 7.66(13) . . . . ?
C2 C7 C8 C9 11.32(10) . . . . ?
C6 C7 C8 C9 -167.88(7) . . . . ?
C11 O1 C9 O2 9.85(8) . . . . ?
C11 O1 C9 N1 128.25(7) . . . . ?
C11 O1 C9 C8 -106.31(7) . . . . ?
C10 O2 C9 O1 -27.14(7) . . . . ?
C10 O2 C9 N1 -146.40(6) . . . . ?
C10 O2 C9 C8 89.58(7) . . . . ?
C1 N1 C9 O1 153.53(7) . . . . ?
C16 N1 C9 O1 -48.61(9) . . . . ?
C1 N1 C9 O2 -89.02(9) . . . . ?
C16 N1 C9 O2 68.84(8) . . . . ?
C1 N1 C9 C8 31.21(10) . . . . ?
C16 N1 C9 C8 -170.93(7) . . . . ?
O4 C8 C9 O1 33.15(10) . . . . ?
C7 C8 C9 O1 -151.07(7) . . . . ?
O4 C8 C9 O2 -82.76(9) . . . . ?
C7 C8 C9 O2 93.02(8) . . . . ?
O4 C8 C9 N1 156.36(8) . . . . ?
C7 C8 C9 N1 -27.86(9) . . . . ?
C9 O2 C10 C13 177.71(7) . . . . ?
C9 O2 C10 C11 32.58(7) . . . . ?
C9 O2 C10 C12 -111.46(8) . . . . ?
C9 O1 C11 C14 156.63(7) . . . . ?
C9 O1 C11 C10 10.32(8) . . . . ?
C9 O1 C11 C15 -133.16(7) . . . . ?
O2 C10 C11 O1 -26.44(8) . . . . ?
C13 C10 C11 O1 -167.63(8) . . . . ?
C12 C10 C11 O1 113.85(8) . . . . ?
O2 C10 C11 C14 -169.01(7) . . . . ?
C13 C10 C11 C14 49.79(12) . . . . ?
C12 C10 C11 C14 -28.72(12) . . . . ?
O2 C10 C11 C15 112.75(9) . . . . ?
C13 C10 C11 C15 -28.44(13) . . . . ?
C12 C10 C11 C15 -106.96(10) . . . . ?
O2 C10 C12 C13 -108.56(8) . . . . ?
C11 C10 C12 C13 116.20(9) . . . . ?
O2 C10 C13 C12 108.47(8) . . . . ?
C11 C10 C13 C12 -115.24(9) . . . . ?
O1 C11 C14 C15 106.76(8) . . . . ?
C10 C11 C14 C15 -114.89(9) . . . . ?
O1 C11 C15 C14 -108.89(8) . . . . ?
C10 C11 C15 C14 116.03(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        35.10
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.073

#=============================================================================
#End of CIF


# Attachment '- compound 20.cif'

data_wdd63_0m
_database_code_depnum_ccdc_archive 'CCDC 859787'
#TrackingRef '- compound 20.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H27 N O4'
_chemical_formula_sum            'C22 H27 N O4'
_chemical_formula_weight         369.45

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_Hall  '-P 2ybc'
_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                   13.2402(4)
_cell_length_b                   8.7479(2)
_cell_length_c                   19.2827(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.821(2)
_cell_angle_gamma                90.00
_cell_volume                     1855.46(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    3963
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      27.70
_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.094
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_max          0.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9774
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2009)'
_exptl_special_details           
;
The crystal was placed in the cold stream of an Oxford Cryosystems
Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating
at 100.0 (1) K.
;
_diffrn_ambient_temperature      100
_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 SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21208
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         30.11
_reflns_number_total             5444
_reflns_number_gt                3902
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_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^)+(0.0369P)^2^+0.8173P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5444
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          <0.001
_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 0.29221(11) 0.76463(12) 0.68429(8) 0.0302(3) Uani 1 1 d . . .
O2 O 0.19765(10) 0.55552(11) 0.70029(7) 0.0235(2) Uani 1 1 d . . .
O3 O 0.42550(11) 0.50349(13) 0.84551(8) 0.0351(3) Uani 1 1 d . . .
O4 O 0.47600(12) 0.74387(15) 0.84830(9) 0.0427(3) Uani 1 1 d . . .
N1 N 0.11472(14) 0.91173(14) 0.62900(9) 0.0278(3) Uani 1 1 d . . .
C1 C 0.20113(18) 0.85694(17) 0.62589(11) 0.0303(4) Uani 1 1 d . . .
C2 C 0.12182(15) 0.88797(17) 0.70426(10) 0.0229(3) Uani 1 1 d . . .
C3 C 0.04930(15) 0.97824(18) 0.71971(11) 0.0263(3) Uani 1 1 d . . .
H3A H -0.0090 1.0459 0.6779 0.032 Uiso 1 1 calc R . .
C4 C 0.06257(16) 0.96893(18) 0.79610(11) 0.0299(4) Uani 1 1 d . . .
H4A H 0.0135 1.0305 0.8067 0.036 Uiso 1 1 calc R . .
C5 C 0.14703(17) 0.87030(19) 0.85705(11) 0.0303(4) Uani 1 1 d . . .
H5A H 0.1567 0.8657 0.9096 0.036 Uiso 1 1 calc R . .
C6 C 0.21790(16) 0.77780(18) 0.84162(10) 0.0265(3) Uani 1 1 d . . .
H6A H 0.2755 0.7096 0.8834 0.032 Uiso 1 1 calc R . .
C7 C 0.20398(14) 0.78571(16) 0.76475(10) 0.0219(3) Uani 1 1 d . . .
C8 C 0.27117(15) 0.68305(17) 0.74059(10) 0.0244(3) Uani 1 1 d . . .
C9 C 0.39965(16) 0.64578(19) 0.81521(12) 0.0312(4) Uani 1 1 d . . .
C10 C 0.33941(15) 0.37453(18) 0.80245(11) 0.0288(4) Uani 1 1 d . . .
C11 C 0.42340(18) 0.2359(2) 0.82506(14) 0.0435(5) Uani 1 1 d . . .
H11A H 0.3735 0.1450 0.7949 0.052 Uiso 1 1 calc R . .
H11B H 0.4783 0.2549 0.8063 0.052 Uiso 1 1 calc R . .
C12 C 0.4996(2) 0.2026(2) 0.91855(16) 0.0557(6) Uani 1 1 d . . .
H12A H 0.5473 0.1081 0.9290 0.067 Uiso 1 1 calc R . .
H12B H 0.5577 0.2876 0.9481 0.067 Uiso 1 1 calc R . .
C13 C 0.42202(19) 0.1834(2) 0.95345(14) 0.0463(5) Uani 1 1 d . . .
H13A H 0.4750 0.1661 1.0145 0.056 Uiso 1 1 calc R . .
H13B H 0.3685 0.0932 0.9276 0.056 Uiso 1 1 calc R . .
C14 C 0.34473(17) 0.3265(2) 0.93546(11) 0.0362(4) Uani 1 1 d . . .
H14A H 0.2921 0.3119 0.9564 0.043 Uiso 1 1 calc R . .
H14B H 0.3984 0.4152 0.9649 0.043 Uiso 1 1 calc R . .
C15 C 0.26616(15) 0.35792(18) 0.84177(10) 0.0261(3) Uani 1 1 d . . .
H15A H 0.2193 0.4530 0.8317 0.031 Uiso 1 1 calc R . .
H15B H 0.2072 0.2733 0.8137 0.031 Uiso 1 1 calc R . .
C16 C 0.25942(16) 0.41054(17) 0.70832(11) 0.0273(4) Uani 1 1 d . . .
C17 C 0.15609(17) 0.29537(17) 0.66093(11) 0.0296(4) Uani 1 1 d . . .
H17A H 0.1912 0.1914 0.6714 0.036 Uiso 1 1 calc R . .
H17B H 0.1045 0.2993 0.6833 0.036 Uiso 1 1 calc R . .
C18 C 0.0765(2) 0.3226(2) 0.56726(11) 0.0393(5) Uani 1 1 d . . .
H18A H 0.0310 0.4193 0.5560 0.047 Uiso 1 1 calc R . .
H18B H 0.0167 0.2385 0.5404 0.047 Uiso 1 1 calc R . .
C19 C 0.1510(2) 0.3314(2) 0.52920(14) 0.0517(6) Uani 1 1 d . . .
H19A H 0.1888 0.2309 0.5342 0.062 Uiso 1 1 calc R . .
H19B H 0.0971 0.3571 0.4692 0.062 Uiso 1 1 calc R . .
C20 C 0.2494(2) 0.4523(2) 0.57365(14) 0.0479(6) Uani 1 1 d . . .
H20A H 0.2111 0.5542 0.5639 0.058 Uiso 1 1 calc R . .
H20B H 0.2996 0.4534 0.5502 0.058 Uiso 1 1 calc R . .
C21 C 0.3306(2) 0.4219(2) 0.66719(13) 0.0404(5) Uani 1 1 d . . .
H21A H 0.3911 0.5052 0.6942 0.048 Uiso 1 1 calc R . .
H21B H 0.3755 0.3252 0.6768 0.048 Uiso 1 1 calc R . .
C22 C 0.2195(2) 0.89864(19) 0.55832(13) 0.0418(5) Uani 1 1 d . . .
H22A H 0.1495 0.9578 0.5152 0.063 Uiso 1 1 calc R . .
H22B H 0.2273 0.8053 0.5336 0.063 Uiso 1 1 calc R . .
H22C H 0.2935 0.9601 0.5820 0.063 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 0.0442(7) 0.0184(6) 0.0532(7) 0.0029(5) 0.0426(7) -0.0005(5)
O2 0.0315(6) 0.0129(5) 0.0397(6) -0.0010(4) 0.0283(5) -0.0008(4)
O3 0.0257(6) 0.0248(6) 0.0591(8) 0.0071(5) 0.0263(6) 0.0009(5)
O4 0.0319(7) 0.0348(7) 0.0669(9) 0.0026(6) 0.0310(7) -0.0107(6)
N1 0.0433(9) 0.0161(6) 0.0366(8) -0.0007(5) 0.0300(7) -0.0021(6)
C1 0.0523(11) 0.0125(7) 0.0455(10) -0.0029(6) 0.0392(9) -0.0054(7)
C2 0.0287(8) 0.0161(7) 0.0331(8) -0.0037(6) 0.0230(7) -0.0056(6)
C3 0.0273(8) 0.0183(7) 0.0418(9) -0.0003(6) 0.0246(8) -0.0011(6)
C4 0.0364(10) 0.0215(8) 0.0513(10) -0.0061(7) 0.0365(9) -0.0039(7)
C5 0.0412(10) 0.0266(8) 0.0384(9) -0.0063(7) 0.0316(8) -0.0076(7)
C6 0.0306(9) 0.0226(8) 0.0341(8) -0.0023(6) 0.0228(7) -0.0048(7)
C7 0.0254(8) 0.0155(7) 0.0364(8) -0.0033(6) 0.0244(7) -0.0053(6)
C8 0.0317(9) 0.0153(7) 0.0411(9) 0.0003(6) 0.0294(8) -0.0034(6)
C9 0.0286(9) 0.0244(8) 0.0545(11) 0.0020(7) 0.0317(9) -0.0022(7)
C10 0.0258(9) 0.0193(8) 0.0515(10) 0.0031(7) 0.0279(8) 0.0010(6)
C11 0.0387(11) 0.0268(10) 0.0803(15) 0.0104(9) 0.0426(11) 0.0115(8)
C12 0.0375(12) 0.0336(11) 0.0895(17) 0.0230(11) 0.0313(12) 0.0172(9)
C13 0.0409(11) 0.0291(10) 0.0555(12) 0.0147(9) 0.0186(10) 0.0031(8)
C14 0.0360(10) 0.0290(9) 0.0392(10) 0.0067(7) 0.0182(8) -0.0019(8)
C15 0.0246(8) 0.0226(8) 0.0378(9) 0.0047(6) 0.0217(7) 0.0019(6)
C16 0.0388(10) 0.0138(7) 0.0513(10) 0.0021(6) 0.0387(9) 0.0028(6)
C17 0.0476(11) 0.0146(7) 0.0466(10) -0.0018(6) 0.0385(9) -0.0027(7)
C18 0.0688(14) 0.0210(8) 0.0451(10) -0.0064(7) 0.0422(11) -0.0105(9)
C19 0.110(2) 0.0205(9) 0.0650(13) -0.0055(8) 0.0733(15) -0.0059(10)
C20 0.0951(17) 0.0197(9) 0.0790(15) -0.0007(9) 0.0795(15) -0.0017(10)
C21 0.0614(13) 0.0198(8) 0.0793(14) 0.0020(8) 0.0637(12) 0.0025(8)
C22 0.0813(16) 0.0189(8) 0.0591(12) -0.0008(8) 0.0602(12) -0.0035(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 C1 1.365(2) . ?
O1 C8 1.4499(17) . ?
O2 C8 1.3979(18) . ?
O2 C16 1.4698(18) . ?
O3 C9 1.336(2) . ?
O3 C10 1.486(2) . ?
O4 C9 1.203(2) . ?
N1 C1 1.272(2) . ?
N1 C2 1.4164(19) . ?
C1 C22 1.497(2) . ?
C2 C7 1.390(2) . ?
C2 C3 1.397(2) . ?
C3 C4 1.385(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.383(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.391(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.390(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.509(2) . ?
C8 C9 1.531(2) . ?
C10 C15 1.535(2) . ?
C10 C11 1.535(2) . ?
C10 C16 1.541(2) . ?
C11 C12 1.526(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.519(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.530(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.526(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.527(2) . ?
C16 C21 1.536(2) . ?
C17 C18 1.520(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.525(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.519(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.524(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C1 O1 C8 117.34(12) . . ?
C8 O2 C16 117.10(12) . . ?
C9 O3 C10 122.20(14) . . ?
C1 N1 C2 116.39(15) . . ?
N1 C1 O1 126.07(14) . . ?
N1 C1 C22 122.33(17) . . ?
O1 C1 C22 111.44(15) . . ?
C7 C2 C3 119.64(14) . . ?
C7 C2 N1 121.93(13) . . ?
C3 C2 N1 118.29(14) . . ?
C4 C3 C2 119.86(16) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C5 C4 C3 120.28(15) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 120.25(14) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C7 C6 C5 119.63(16) . . ?
C7 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
C2 C7 C6 120.28(14) . . ?
C2 C7 C8 116.40(13) . . ?
C6 C7 C8 123.28(15) . . ?
O2 C8 O1 109.94(12) . . ?
O2 C8 C7 107.39(12) . . ?
O1 C8 C7 109.28(12) . . ?
O2 C8 C9 114.71(13) . . ?
O1 C8 C9 103.43(12) . . ?
C7 C8 C9 111.97(13) . . ?
O4 C9 O3 119.83(17) . . ?
O4 C9 C8 120.83(15) . . ?
O3 C9 C8 119.30(14) . . ?
O3 C10 C15 107.17(13) . . ?
O3 C10 C11 103.40(14) . . ?
C15 C10 C11 110.00(14) . . ?
O3 C10 C16 108.26(12) . . ?
C15 C10 C16 113.10(13) . . ?
C11 C10 C16 114.21(15) . . ?
C12 C11 C10 112.61(17) . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 112.26(17) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 109.93(16) . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 C13 110.18(16) . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C10 113.58(14) . . ?
C14 C15 H15A 108.8 . . ?
C10 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C10 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
O2 C16 C17 104.22(13) . . ?
O2 C16 C21 110.82(12) . . ?
C17 C16 C21 109.67(14) . . ?
O2 C16 C10 106.12(12) . . ?
C17 C16 C10 111.68(12) . . ?
C21 C16 C10 113.85(15) . . ?
C18 C17 C16 113.91(13) . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 C19 111.95(18) . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C20 C19 C18 110.18(14) . . ?
C20 C19 H19A 109.6 . . ?
C18 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C19 C20 C21 111.39(15) . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 C16 113.01(17) . . ?
C20 C21 H21A 109.0 . . ?
C16 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
C16 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C1 C22 H22A 109.5 . . ?
C1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C2 N1 C1 O1 7.4(2) . . . . ?
C2 N1 C1 C22 -167.59(15) . . . . ?
C8 O1 C1 N1 20.4(2) . . . . ?
C8 O1 C1 C22 -164.16(13) . . . . ?
C1 N1 C2 C7 -12.5(2) . . . . ?
C1 N1 C2 C3 163.15(15) . . . . ?
C7 C2 C3 C4 2.1(2) . . . . ?
N1 C2 C3 C4 -173.60(15) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C4 C5 C6 C7 0.4(2) . . . . ?
C3 C2 C7 C6 -2.8(2) . . . . ?
N1 C2 C7 C6 172.78(14) . . . . ?
C3 C2 C7 C8 174.98(14) . . . . ?
N1 C2 C7 C8 -9.5(2) . . . . ?
C5 C6 C7 C2 1.5(2) . . . . ?
C5 C6 C7 C8 -176.09(14) . . . . ?
C16 O2 C8 O1 91.41(15) . . . . ?
C16 O2 C8 C7 -149.79(12) . . . . ?
C16 O2 C8 C9 -24.63(17) . . . . ?
C1 O1 C8 O2 78.59(16) . . . . ?
C1 O1 C8 C7 -39.05(18) . . . . ?
C1 O1 C8 C9 -158.46(13) . . . . ?
C2 C7 C8 O2 -85.75(15) . . . . ?
C6 C7 C8 O2 91.95(18) . . . . ?
C2 C7 C8 O1 33.48(19) . . . . ?
C6 C7 C8 O1 -148.82(15) . . . . ?
C2 C7 C8 C9 147.47(14) . . . . ?
C6 C7 C8 C9 -34.8(2) . . . . ?
C10 O3 C9 O4 -173.71(15) . . . . ?
C10 O3 C9 C8 8.6(2) . . . . ?
O2 C8 C9 O4 170.53(15) . . . . ?
O1 C8 C9 O4 50.79(19) . . . . ?
C7 C8 C9 O4 -66.75(19) . . . . ?
O2 C8 C9 O3 -11.8(2) . . . . ?
O1 C8 C9 O3 -131.59(14) . . . . ?
C7 C8 C9 O3 110.87(16) . . . . ?
C9 O3 C10 C15 -94.85(17) . . . . ?
C9 O3 C10 C11 148.95(15) . . . . ?
C9 O3 C10 C16 27.44(19) . . . . ?
O3 C10 C11 C12 63.43(19) . . . . ?
C15 C10 C11 C12 -50.7(2) . . . . ?
C16 C10 C11 C12 -179.16(16) . . . . ?
C10 C11 C12 C13 54.7(2) . . . . ?
C11 C12 C13 C14 -57.1(2) . . . . ?
C12 C13 C14 C15 57.2(2) . . . . ?
C13 C14 C15 C10 -56.45(19) . . . . ?
O3 C10 C15 C14 -59.21(17) . . . . ?
C11 C10 C15 C14 52.5(2) . . . . ?
C16 C10 C15 C14 -178.44(13) . . . . ?
C8 O2 C16 C17 178.03(11) . . . . ?
C8 O2 C16 C21 -64.07(18) . . . . ?
C8 O2 C16 C10 60.01(15) . . . . ?
O3 C10 C16 O2 -58.67(14) . . . . ?
C15 C10 C16 O2 59.93(16) . . . . ?
C11 C10 C16 O2 -173.25(13) . . . . ?
O3 C10 C16 C17 -171.63(12) . . . . ?
C15 C10 C16 C17 -53.03(17) . . . . ?
C11 C10 C16 C17 73.79(17) . . . . ?
O3 C10 C16 C21 63.49(16) . . . . ?
C15 C10 C16 C21 -177.91(13) . . . . ?
C11 C10 C16 C21 -51.09(19) . . . . ?
O2 C16 C17 C18 67.66(16) . . . . ?
C21 C16 C17 C18 -51.03(19) . . . . ?
C10 C16 C17 C18 -178.20(14) . . . . ?
C16 C17 C18 C19 53.75(19) . . . . ?
C17 C18 C19 C20 -55.0(2) . . . . ?
C18 C19 C20 C21 56.3(2) . . . . ?
C19 C20 C21 C16 -56.3(2) . . . . ?
O2 C16 C21 C20 -62.34(19) . . . . ?
C17 C16 C21 C20 52.17(18) . . . . ?
C10 C16 C21 C20 178.12(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        30.11
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046
# Attachment '- compound 21.cif'

data_wdd61_0m
_database_code_depnum_ccdc_archive 'CCDC 859788'
#TrackingRef '- compound 21.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H27 N O3'
_chemical_formula_sum            'C22 H27 N O3'
_chemical_formula_weight         353.45

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                   9.0404(2)
_cell_length_b                   9.9839(3)
_cell_length_c                   10.8814(3)
_cell_angle_alpha                90.8800(10)
_cell_angle_beta                 103.8590(10)
_cell_angle_gamma                111.0820(10)
_cell_volume                     884.12(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      35.03
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9496
_exptl_absorpt_correction_T_max  0.9737
_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2009)'
_exptl_special_details           
;
The crystal was placed in the cold stream of an Oxford Cryosystems
Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating
at 100.0 (1) K.
;
_diffrn_ambient_temperature      100
_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 SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28220
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         35.10
_reflns_number_total             7740
_reflns_number_gt                6619
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_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^)+(0.0728P)^2^+0.1957P] 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         7740
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1241
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
O1 O 0.78569(8) 0.91932(6) 0.42358(6) 0.01728(12) Uani 1 1 d . . .
O2 O 0.98408(7) 1.22777(7) 0.50495(6) 0.01661(11) Uani 1 1 d . . .
O3 O 0.30311(9) 0.89545(9) 0.31371(10) 0.0357(2) Uani 1 1 d . . .
N1 N 0.57934(8) 1.01144(7) 0.35789(7) 0.01451(12) Uani 1 1 d . . .
C1 C 0.74251(9) 1.01866(8) 0.39359(7) 0.01360(13) Uani 1 1 d . . .
C2 C 0.58105(10) 1.15568(8) 0.36159(7) 0.01411(13) Uani 1 1 d . . .
C3 C 0.45054(10) 1.20143(10) 0.35231(8) 0.01759(14) Uani 1 1 d . . .
C4 C 0.48802(11) 1.35029(10) 0.36760(8) 0.01929(15) Uani 1 1 d . . .
C5 C 0.64894(11) 1.44953(9) 0.39239(8) 0.01850(15) Uani 1 1 d . . .
C6 C 0.77778(10) 1.40166(9) 0.39992(8) 0.01618(14) Uani 1 1 d . . .
C7 C 0.74275(9) 1.25443(8) 0.38252(7) 0.01363(13) Uani 1 1 d . . .
C8 C 0.85779(9) 1.17502(8) 0.39018(7) 0.01292(12) Uani 1 1 d . . .
C9 C 0.93622(9) 1.17269(8) 0.27626(7) 0.01262(12) Uani 1 1 d . . .
C10 C 1.03940(10) 1.32505(8) 0.24840(8) 0.01569(13) Uani 1 1 d . . .
C11 C 0.94445(11) 1.39862(8) 0.15592(8) 0.01697(14) Uani 1 1 d . . .
C12 C 0.83015(10) 1.29785(8) 0.03693(8) 0.01590(14) Uani 1 1 d . . .
C13 C 0.71743(9) 1.15793(8) 0.07506(7) 0.01382(13) Uani 1 1 d . . .
C14 C 0.82098(9) 1.08303(8) 0.15260(7) 0.01187(12) Uani 1 1 d . . .
C15 C 0.82985(9) 0.95917(8) 0.10822(7) 0.01271(12) Uani 1 1 d . . .
C16 C 0.73125(10) 0.87629(8) -0.02109(7) 0.01512(13) Uani 1 1 d . . .
C17 C 0.63063(10) 0.71822(8) -0.00974(8) 0.01652(14) Uani 1 1 d . . .
C18 C 0.74146(11) 0.64337(8) 0.06060(8) 0.01775(14) Uani 1 1 d . . .
C19 C 0.84675(10) 0.72805(8) 0.18934(8) 0.01683(14) Uani 1 1 d . . .
C20 C 0.94210(10) 0.88732(8) 0.17775(8) 0.01488(13) Uani 1 1 d . . .
C21 C 0.43490(10) 0.88496(9) 0.32685(8) 0.01844(15) Uani 1 1 d . . .
C22 C 0.45230(12) 0.74294(10) 0.30722(9) 0.02083(16) Uani 1 1 d . . .
H1O2 H 1.041(2) 1.168(2) 0.5136(18) 0.047(5) Uiso 1 1 d . . .
H3 H 0.3435(18) 1.1383(15) 0.3399(14) 0.024(3) Uiso 1 1 d . . .
H4 H 0.3982(18) 1.3843(15) 0.3650(14) 0.027(3) Uiso 1 1 d . . .
H5 H 0.6744(18) 1.5573(16) 0.4069(14) 0.028(3) Uiso 1 1 d . . .
H6 H 0.8904(17) 1.4718(14) 0.4148(13) 0.021(3) Uiso 1 1 d . . .
H9 H 1.0153(16) 1.1241(14) 0.3137(13) 0.020(3) Uiso 1 1 d . . .
H10A H 1.0972(17) 1.3868(15) 0.3298(14) 0.024(3) Uiso 1 1 d . . .
H10B H 1.1251(16) 1.3119(14) 0.2104(13) 0.020(3) Uiso 1 1 d . . .
H11A H 1.0243(18) 1.4887(15) 0.1331(14) 0.025(3) Uiso 1 1 d . . .
H11B H 0.8741(15) 1.4326(13) 0.1958(12) 0.017(3) Uiso 1 1 d . . .
H12A H 0.7601(16) 1.3444(14) -0.0177(13) 0.020(3) Uiso 1 1 d . . .
H12B H 0.8933(17) 1.2736(14) -0.0154(13) 0.022(3) Uiso 1 1 d . . .
H13A H 0.6377(16) 1.0950(14) -0.0021(13) 0.021(3) Uiso 1 1 d . . .
H13B H 0.6513(17) 1.1841(15) 0.1275(13) 0.023(3) Uiso 1 1 d . . .
H16A H 0.6572(16) 0.9226(14) -0.0726(12) 0.018(3) Uiso 1 1 d . . .
H16B H 0.8097(17) 0.8763(15) -0.0719(13) 0.023(3) Uiso 1 1 d . . .
H17A H 0.5669(17) 0.6678(15) -0.0971(14) 0.026(3) Uiso 1 1 d . . .
H17B H 0.5457(16) 0.7154(14) 0.0373(13) 0.022(3) Uiso 1 1 d . . .
H18A H 0.6702(17) 0.5428(15) 0.0713(13) 0.024(3) Uiso 1 1 d . . .
H18B H 0.8123(17) 0.6327(15) 0.0063(13) 0.024(3) Uiso 1 1 d . . .
H19A H 0.7757(16) 0.7234(14) 0.2458(13) 0.019(3) Uiso 1 1 d . . .
H19B H 0.9277(18) 0.6860(15) 0.2322(14) 0.026(3) Uiso 1 1 d . . .
H20A H 1.0023(16) 0.9351(14) 0.2599(13) 0.020(3) Uiso 1 1 d . . .
H20B H 1.0205(16) 0.8918(14) 0.1268(13) 0.020(3) Uiso 1 1 d . . .
H22A H 0.520(2) 0.7459(18) 0.2533(17) 0.043(4) Uiso 1 1 d . . .
H22B H 0.344(2) 0.6749(18) 0.2717(16) 0.041(4) Uiso 1 1 d . . .
H22C H 0.504(2) 0.7166(17) 0.3877(16) 0.039(4) Uiso 1 1 d . . .

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 0.0179(3) 0.0166(2) 0.0194(3) 0.0040(2) 0.0035(2) 0.0097(2)
O2 0.0161(2) 0.0185(3) 0.0136(2) -0.00177(19) -0.0023(2) 0.0087(2)
O3 0.0148(3) 0.0259(3) 0.0640(6) 0.0076(4) 0.0057(3) 0.0075(3)
N1 0.0129(3) 0.0157(3) 0.0154(3) 0.0021(2) 0.0024(2) 0.0068(2)
C1 0.0130(3) 0.0158(3) 0.0126(3) 0.0015(2) 0.0020(2) 0.0070(2)
C2 0.0152(3) 0.0173(3) 0.0120(3) 0.0017(2) 0.0030(2) 0.0090(3)
C3 0.0171(3) 0.0241(4) 0.0158(3) 0.0032(3) 0.0046(3) 0.0125(3)
C4 0.0219(4) 0.0256(4) 0.0173(3) 0.0031(3) 0.0056(3) 0.0166(3)
C5 0.0243(4) 0.0205(3) 0.0156(3) 0.0016(3) 0.0047(3) 0.0145(3)
C6 0.0195(3) 0.0165(3) 0.0150(3) 0.0003(2) 0.0036(3) 0.0102(3)
C7 0.0147(3) 0.0158(3) 0.0120(3) 0.0008(2) 0.0021(2) 0.0086(2)
C8 0.0124(3) 0.0136(3) 0.0126(3) 0.0001(2) 0.0006(2) 0.0065(2)
C9 0.0114(3) 0.0123(3) 0.0143(3) -0.0002(2) 0.0017(2) 0.0057(2)
C10 0.0136(3) 0.0133(3) 0.0182(3) -0.0003(2) 0.0036(3) 0.0032(2)
C11 0.0202(3) 0.0123(3) 0.0190(3) 0.0023(2) 0.0066(3) 0.0058(3)
C12 0.0190(3) 0.0146(3) 0.0166(3) 0.0040(2) 0.0060(3) 0.0083(3)
C13 0.0134(3) 0.0141(3) 0.0148(3) 0.0021(2) 0.0022(2) 0.0070(2)
C14 0.0115(3) 0.0115(3) 0.0126(3) 0.0010(2) 0.0019(2) 0.0052(2)
C15 0.0135(3) 0.0118(3) 0.0131(3) 0.0011(2) 0.0029(2) 0.0054(2)
C16 0.0184(3) 0.0130(3) 0.0131(3) 0.0006(2) 0.0033(3) 0.0054(2)
C17 0.0166(3) 0.0136(3) 0.0164(3) -0.0002(2) 0.0026(3) 0.0034(2)
C18 0.0197(3) 0.0121(3) 0.0208(4) 0.0005(3) 0.0050(3) 0.0055(3)
C19 0.0196(3) 0.0133(3) 0.0187(3) 0.0028(2) 0.0039(3) 0.0081(3)
C20 0.0146(3) 0.0121(3) 0.0183(3) 0.0005(2) 0.0026(3) 0.0066(2)
C21 0.0149(3) 0.0188(3) 0.0195(3) 0.0038(3) 0.0026(3) 0.0051(3)
C22 0.0205(4) 0.0185(3) 0.0207(4) 0.0009(3) 0.0036(3) 0.0053(3)

_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 C1 1.2125(9) . ?
O2 C8 1.4159(9) . ?
O2 H1O2 0.908(19) . ?
O3 C21 1.2081(11) . ?
N1 C1 1.4071(10) . ?
N1 C21 1.4153(11) . ?
N1 C2 1.4345(10) . ?
C1 C8 1.5409(11) . ?
C2 C3 1.3939(11) . ?
C2 C7 1.3991(11) . ?
C3 C4 1.3980(12) . ?
C3 H3 0.920(14) . ?
C4 C5 1.3920(13) . ?
C4 H4 0.982(14) . ?
C5 C6 1.3957(11) . ?
C5 H5 1.017(14) . ?
C6 C7 1.3873(11) . ?
C6 H6 0.979(13) . ?
C7 C8 1.5069(10) . ?
C8 C9 1.5724(11) . ?
C9 C14 1.5224(10) . ?
C9 C10 1.5507(11) . ?
C9 H9 1.015(14) . ?
C10 C11 1.5334(12) . ?
C10 H10A 0.984(14) . ?
C10 H10B 1.006(13) . ?
C11 C12 1.5256(12) . ?
C11 H11A 1.009(14) . ?
C11 H11B 0.996(12) . ?
C12 C13 1.5357(11) . ?
C12 H12A 1.006(14) . ?
C12 H12B 0.980(14) . ?
C13 C14 1.5140(10) . ?
C13 H13A 0.993(14) . ?
C13 H13B 1.011(13) . ?
C14 C15 1.3566(10) . ?
C15 C20 1.5131(11) . ?
C15 C16 1.5139(11) . ?
C16 C17 1.5363(11) . ?
C16 H16A 1.014(13) . ?
C16 H16B 0.998(13) . ?
C17 C18 1.5287(12) . ?
C17 H17A 1.002(14) . ?
C17 H17B 1.013(13) . ?
C18 C19 1.5261(12) . ?
C18 H18A 1.005(14) . ?
C18 H18B 1.000(13) . ?
C19 C20 1.5361(11) . ?
C19 H19A 0.980(13) . ?
C19 H19B 0.997(15) . ?
C20 H20A 0.944(14) . ?
C20 H20B 0.989(13) . ?
C21 C22 1.4994(13) . ?
C22 H22A 0.939(17) . ?
C22 H22B 0.950(17) . ?
C22 H22C 0.977(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
C8 O2 H1O2 106.6(12) . . ?
C1 N1 C21 126.90(7) . . ?
C1 N1 C2 108.68(6) . . ?
C21 N1 C2 124.39(7) . . ?
O1 C1 N1 125.93(7) . . ?
O1 C1 C8 125.59(7) . . ?
N1 C1 C8 108.47(6) . . ?
C3 C2 C7 121.52(7) . . ?
C3 C2 N1 128.98(7) . . ?
C7 C2 N1 109.45(6) . . ?
C2 C3 C4 117.30(8) . . ?
C2 C3 H3 122.9(9) . . ?
C4 C3 H3 119.8(9) . . ?
C5 C4 C3 121.73(7) . . ?
C5 C4 H4 119.8(8) . . ?
C3 C4 H4 118.4(8) . . ?
C4 C5 C6 120.12(8) . . ?
C4 C5 H5 120.7(8) . . ?
C6 C5 H5 119.2(8) . . ?
C7 C6 C5 119.01(8) . . ?
C7 C6 H6 121.1(8) . . ?
C5 C6 H6 119.9(8) . . ?
C6 C7 C2 120.27(7) . . ?
C6 C7 C8 129.61(7) . . ?
C2 C7 C8 110.01(6) . . ?
O2 C8 C7 108.68(6) . . ?
O2 C8 C1 111.40(6) . . ?
C7 C8 C1 101.37(6) . . ?
O2 C8 C9 109.36(6) . . ?
C7 C8 C9 118.84(6) . . ?
C1 C8 C9 106.91(6) . . ?
C14 C9 C10 109.89(6) . . ?
C14 C9 C8 116.59(6) . . ?
C10 C9 C8 113.67(6) . . ?
C14 C9 H9 108.2(7) . . ?
C10 C9 H9 107.5(7) . . ?
C8 C9 H9 100.0(7) . . ?
C11 C10 C9 115.78(6) . . ?
C11 C10 H10A 110.4(8) . . ?
C9 C10 H10A 108.6(8) . . ?
C11 C10 H10B 108.4(8) . . ?
C9 C10 H10B 105.8(7) . . ?
H10A C10 H10B 107.4(11) . . ?
C12 C11 C10 112.55(6) . . ?
C12 C11 H11A 111.2(8) . . ?
C10 C11 H11A 109.6(9) . . ?
C12 C11 H11B 106.3(8) . . ?
C10 C11 H11B 111.8(7) . . ?
H11A C11 H11B 105.1(11) . . ?
C11 C12 C13 109.93(6) . . ?
C11 C12 H12A 111.3(7) . . ?
C13 C12 H12A 108.8(7) . . ?
C11 C12 H12B 110.8(8) . . ?
C13 C12 H12B 108.9(8) . . ?
H12A C12 H12B 107.1(11) . . ?
C14 C13 C12 109.41(6) . . ?
C14 C13 H13A 112.0(8) . . ?
C12 C13 H13A 110.1(8) . . ?
C14 C13 H13B 110.1(8) . . ?
C12 C13 H13B 108.2(8) . . ?
H13A C13 H13B 106.9(11) . . ?
C15 C14 C13 123.47(7) . . ?
C15 C14 C9 122.47(6) . . ?
C13 C14 C9 113.30(6) . . ?
C14 C15 C20 125.33(7) . . ?
C14 C15 C16 124.04(7) . . ?
C20 C15 C16 110.60(6) . . ?
C15 C16 C17 111.53(6) . . ?
C15 C16 H16A 113.4(7) . . ?
C17 C16 H16A 110.1(7) . . ?
C15 C16 H16B 108.1(8) . . ?
C17 C16 H16B 107.7(8) . . ?
H16A C16 H16B 105.6(11) . . ?
C18 C17 C16 111.05(7) . . ?
C18 C17 H17A 112.0(8) . . ?
C16 C17 H17A 108.9(8) . . ?
C18 C17 H17B 109.9(8) . . ?
C16 C17 H17B 109.1(7) . . ?
H17A C17 H17B 105.8(11) . . ?
C19 C18 C17 111.12(6) . . ?
C19 C18 H18A 111.0(8) . . ?
C17 C18 H18A 108.4(8) . . ?
C19 C18 H18B 110.6(8) . . ?
C17 C18 H18B 109.1(8) . . ?
H18A C18 H18B 106.5(11) . . ?
C18 C19 C20 112.27(7) . . ?
C18 C19 H19A 109.1(8) . . ?
C20 C19 H19A 108.8(7) . . ?
C18 C19 H19B 111.9(8) . . ?
C20 C19 H19B 107.9(8) . . ?
H19A C19 H19B 106.7(11) . . ?
C15 C20 C19 111.84(6) . . ?
C15 C20 H20A 112.3(8) . . ?
C19 C20 H20A 108.8(8) . . ?
C15 C20 H20B 106.9(8) . . ?
C19 C20 H20B 108.5(7) . . ?
H20A C20 H20B 108.4(11) . . ?
O3 C21 N1 119.29(8) . . ?
O3 C21 C22 122.65(8) . . ?
N1 C21 C22 118.02(7) . . ?
C21 C22 H22A 112.2(10) . . ?
C21 C22 H22B 105.7(10) . . ?
H22A C22 H22B 111.0(14) . . ?
C21 C22 H22C 110.9(10) . . ?
H22A C22 H22C 105.6(14) . . ?
H22B C22 H22C 111.5(14) . . ?

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
C21 N1 C1 O1 -12.85(13) . . . . ?
C2 N1 C1 O1 165.31(8) . . . . ?
C21 N1 C1 C8 168.01(7) . . . . ?
C2 N1 C1 C8 -13.82(8) . . . . ?
C1 N1 C2 C3 -169.54(8) . . . . ?
C21 N1 C2 C3 8.69(13) . . . . ?
C1 N1 C2 C7 7.84(9) . . . . ?
C21 N1 C2 C7 -173.93(7) . . . . ?
C7 C2 C3 C4 -1.38(12) . . . . ?
N1 C2 C3 C4 175.72(8) . . . . ?
C2 C3 C4 C5 -0.65(12) . . . . ?
C3 C4 C5 C6 1.39(13) . . . . ?
C4 C5 C6 C7 -0.08(12) . . . . ?
C5 C6 C7 C2 -1.91(12) . . . . ?
C5 C6 C7 C8 -177.63(8) . . . . ?
C3 C2 C7 C6 2.69(12) . . . . ?
N1 C2 C7 C6 -174.92(7) . . . . ?
C3 C2 C7 C8 179.19(7) . . . . ?
N1 C2 C7 C8 1.57(9) . . . . ?
C6 C7 C8 O2 49.38(11) . . . . ?
C2 C7 C8 O2 -126.69(7) . . . . ?
C6 C7 C8 C1 166.82(8) . . . . ?
C2 C7 C8 C1 -9.25(8) . . . . ?
C6 C7 C8 C9 -76.47(10) . . . . ?
C2 C7 C8 C9 107.46(8) . . . . ?
O1 C1 C8 O2 -49.78(10) . . . . ?
N1 C1 C8 O2 129.36(6) . . . . ?
O1 C1 C8 C7 -165.22(8) . . . . ?
N1 C1 C8 C7 13.92(8) . . . . ?
O1 C1 C8 C9 69.65(9) . . . . ?
N1 C1 C8 C9 -111.21(7) . . . . ?
O2 C8 C9 C14 164.07(6) . . . . ?
C7 C8 C9 C14 -70.40(9) . . . . ?
C1 C8 C9 C14 43.34(8) . . . . ?
O2 C8 C9 C10 -66.53(8) . . . . ?
C7 C8 C9 C10 59.00(9) . . . . ?
C1 C8 C9 C10 172.74(6) . . . . ?
C14 C9 C10 C11 44.55(8) . . . . ?
C8 C9 C10 C11 -88.15(8) . . . . ?
C9 C10 C11 C12 -46.53(9) . . . . ?
C10 C11 C12 C13 53.19(9) . . . . ?
C11 C12 C13 C14 -60.42(8) . . . . ?
C12 C13 C14 C15 -108.57(8) . . . . ?
C12 C13 C14 C9 61.65(8) . . . . ?
C10 C9 C14 C15 118.07(8) . . . . ?
C8 C9 C14 C15 -110.75(8) . . . . ?
C10 C9 C14 C13 -52.26(8) . . . . ?
C8 C9 C14 C13 78.92(8) . . . . ?
C13 C14 C15 C20 174.58(7) . . . . ?
C9 C14 C15 C20 5.23(12) . . . . ?
C13 C14 C15 C16 -3.31(12) . . . . ?
C9 C14 C15 C16 -172.65(7) . . . . ?
C14 C15 C16 C17 -124.71(8) . . . . ?
C20 C15 C16 C17 57.14(8) . . . . ?
C15 C16 C17 C18 -56.69(9) . . . . ?
C16 C17 C18 C19 53.84(9) . . . . ?
C17 C18 C19 C20 -52.60(9) . . . . ?
C14 C15 C20 C19 126.51(8) . . . . ?
C16 C15 C20 C19 -55.36(8) . . . . ?
C18 C19 C20 C15 53.68(9) . . . . ?
C1 N1 C21 O3 170.63(9) . . . . ?
C2 N1 C21 O3 -7.26(13) . . . . ?
C1 N1 C21 C22 -11.42(12) . . . . ?
C2 N1 C21 C22 170.68(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        35.10
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.066