# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       zhengjiehe@nankai.edu.cn
_publ_contact_author_name        'Zhengjie He'
loop_
_publ_author_name
'Lingchao Cai'
'Guiping Wu'
'Haibin Song'
'Zhengjie He'

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 782770'
#TrackingRef '3a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 N2 O5'
_chemical_formula_sum            'C26 H24 N2 O5'
_chemical_formula_weight         444.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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

_cell_length_a                   11.9164(13)
_cell_length_b                   11.4393(12)
_cell_length_c                   17.345(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.959(7)
_cell_angle_gamma                90.00
_cell_volume                     2222.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    2895
_cell_measurement_theta_min      27.6
_cell_measurement_theta_max      72.4

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7120
_exptl_absorpt_correction_T_max  0.8629
_exptl_absorpt_process_details   Crystalclear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 14.63
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            31654
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.95
_diffrn_reflns_theta_max         72.48
_reflns_number_total             4351
_reflns_number_gt                3784
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'CrystalStructure 3.8'

_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^)+(0.0721P)^2^+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.0048(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4351
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.36172(7) 0.08056(7) 0.50300(5) 0.0211(2) Uani 1 1 d . . .
O2 O 0.92090(8) 0.25078(8) 0.69575(6) 0.0333(3) Uani 1 1 d . . .
O3 O 0.85700(7) 0.07908(7) 0.63380(5) 0.0227(2) Uani 1 1 d . . .
O4 O 0.62641(8) 0.26150(8) 0.27771(5) 0.0281(2) Uani 1 1 d . . .
O5 O 0.67095(7) 0.08767(7) 0.34114(5) 0.0221(2) Uani 1 1 d . . .
N1 N 0.75721(10) 0.47190(10) 0.59663(7) 0.0310(3) Uani 1 1 d . . .
N2 N 0.57267(9) 0.46273(10) 0.40115(7) 0.0289(3) Uani 1 1 d . . .
C1 C 0.40898(9) 0.17040(10) 0.53518(7) 0.0169(2) Uani 1 1 d . . .
C2 C 0.51280(10) 0.22433(10) 0.51428(7) 0.0158(2) Uani 1 1 d . . .
H2 H 0.5021 0.3110 0.5094 0.019 Uiso 1 1 calc R . .
C3 C 0.62827(9) 0.19589(10) 0.58628(7) 0.0173(3) Uani 1 1 d . . .
H3A H 0.6360 0.1100 0.5928 0.021 Uiso 1 1 calc R . .
H3B H 0.6217 0.2285 0.6374 0.021 Uiso 1 1 calc R . .
C4 C 0.74267(10) 0.24527(10) 0.57433(7) 0.0169(3) Uani 1 1 d . . .
C5 C 0.74669(10) 0.20899(10) 0.48845(7) 0.0154(2) Uani 1 1 d . . .
H5 H 0.7491 0.1216 0.4895 0.018 Uiso 1 1 calc R . .
C6 C 0.62855(10) 0.24045(10) 0.41761(7) 0.0157(2) Uani 1 1 d . . .
C7 C 0.52229(9) 0.17561(10) 0.43393(7) 0.0152(2) Uani 1 1 d . . .
H7 H 0.5463 0.0917 0.4444 0.018 Uiso 1 1 calc R . .
C8 C 0.37155(11) 0.23236(12) 0.59869(8) 0.0281(3) Uani 1 1 d . . .
H8A H 0.2987 0.1962 0.6019 0.042 Uiso 1 1 calc R . .
H8B H 0.3562 0.3149 0.5835 0.042 Uiso 1 1 calc R . .
H8C H 0.4353 0.2265 0.6521 0.042 Uiso 1 1 calc R . .
C9 C 0.85202(10) 0.19410(10) 0.64224(7) 0.0190(3) Uani 1 1 d . . .
C10 C 0.95644(11) 0.02015(13) 0.69396(8) 0.0291(3) Uani 1 1 d . . .
H10A H 0.9429 -0.0645 0.6899 0.044 Uiso 1 1 calc R . .
H10B H 0.9633 0.0468 0.7491 0.044 Uiso 1 1 calc R . .
H10C H 1.0303 0.0383 0.6835 0.044 Uiso 1 1 calc R . .
C11 C 0.75029(10) 0.37296(11) 0.58618(7) 0.0201(3) Uani 1 1 d . . .
C12 C 0.86026(10) 0.24560(10) 0.47322(7) 0.0175(3) Uani 1 1 d . . .
C13 C 0.88058(10) 0.35801(11) 0.45074(7) 0.0207(3) Uani 1 1 d . . .
H13 H 0.8229 0.4174 0.4460 0.025 Uiso 1 1 calc R . .
C14 C 0.98490(11) 0.38446(12) 0.43503(7) 0.0251(3) Uani 1 1 d . . .
H14 H 0.9970 0.4613 0.4186 0.030 Uiso 1 1 calc R . .
C15 C 1.07065(11) 0.29979(12) 0.44314(8) 0.0285(3) Uani 1 1 d . . .
H15 H 1.1419 0.3183 0.4328 0.034 Uiso 1 1 calc R . .
C16 C 1.05237(11) 0.18759(12) 0.46651(9) 0.0299(3) Uani 1 1 d . . .
H16 H 1.1115 0.1291 0.4728 0.036 Uiso 1 1 calc R . .
C17 C 0.94735(10) 0.16076(11) 0.48071(8) 0.0238(3) Uani 1 1 d . . .
H17 H 0.9347 0.0833 0.4958 0.029 Uiso 1 1 calc R . .
C18 C 0.64116(10) 0.19958(11) 0.33649(7) 0.0188(3) Uani 1 1 d . . .
C19 C 0.68838(13) 0.04017(14) 0.26823(8) 0.0343(3) Uani 1 1 d . . .
H19A H 0.7083 -0.0431 0.2766 0.051 Uiso 1 1 calc R . .
H19B H 0.7537 0.0820 0.2580 0.051 Uiso 1 1 calc R . .
H19C H 0.6149 0.0496 0.2210 0.051 Uiso 1 1 calc R . .
C20 C 0.60038(10) 0.36629(10) 0.40802(7) 0.0190(3) Uani 1 1 d . . .
C21 C 0.40855(10) 0.17785(10) 0.35991(7) 0.0167(2) Uani 1 1 d . . .
C22 C 0.38644(10) 0.08685(11) 0.30314(7) 0.0206(3) Uani 1 1 d . . .
H22 H 0.4433 0.0258 0.3112 0.025 Uiso 1 1 calc R . .
C23 C 0.28245(11) 0.08399(12) 0.23480(8) 0.0267(3) Uani 1 1 d . . .
H23 H 0.2693 0.0220 0.1963 0.032 Uiso 1 1 calc R . .
C24 C 0.19826(11) 0.17182(12) 0.22320(8) 0.0285(3) Uani 1 1 d . . .
H24 H 0.1271 0.1704 0.1768 0.034 Uiso 1 1 calc R . .
C25 C 0.21872(11) 0.26182(11) 0.27991(8) 0.0261(3) Uani 1 1 d . . .
H25 H 0.1604 0.3213 0.2726 0.031 Uiso 1 1 calc R . .
C26 C 0.32348(10) 0.26598(10) 0.34722(8) 0.0207(3) Uani 1 1 d . . .
H26 H 0.3372 0.3292 0.3848 0.025 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 0.0183(4) 0.0183(5) 0.0274(4) 0.0006(3) 0.0089(3) -0.0028(3)
O2 0.0236(5) 0.0348(6) 0.0321(5) -0.0084(4) -0.0027(4) -0.0063(4)
O3 0.0164(4) 0.0235(5) 0.0229(4) 0.0023(3) -0.0001(3) -0.0006(3)
O4 0.0286(5) 0.0363(6) 0.0206(4) 0.0062(4) 0.0101(4) 0.0009(4)
O5 0.0213(4) 0.0257(5) 0.0208(4) -0.0034(3) 0.0090(3) 0.0036(3)
N1 0.0373(6) 0.0250(6) 0.0380(6) -0.0067(5) 0.0224(5) -0.0052(5)
N2 0.0235(6) 0.0221(6) 0.0415(7) 0.0070(5) 0.0117(5) 0.0011(4)
C1 0.0121(5) 0.0178(6) 0.0206(6) 0.0029(4) 0.0055(4) 0.0015(4)
C2 0.0132(5) 0.0157(5) 0.0193(5) 0.0006(4) 0.0067(4) 0.0002(4)
C3 0.0129(5) 0.0216(6) 0.0191(6) -0.0006(4) 0.0076(5) -0.0034(4)
C4 0.0142(5) 0.0184(6) 0.0187(6) -0.0017(4) 0.0065(4) -0.0024(4)
C5 0.0125(5) 0.0167(6) 0.0176(5) -0.0002(4) 0.0059(4) -0.0002(4)
C6 0.0127(5) 0.0160(6) 0.0196(6) 0.0016(4) 0.0068(4) 0.0004(4)
C7 0.0124(5) 0.0151(5) 0.0192(5) 0.0010(4) 0.0069(4) 0.0003(4)
C8 0.0223(6) 0.0339(8) 0.0346(7) -0.0081(6) 0.0178(6) -0.0060(5)
C9 0.0138(5) 0.0245(6) 0.0202(6) -0.0014(5) 0.0076(5) -0.0042(5)
C10 0.0185(6) 0.0334(8) 0.0292(7) 0.0078(5) 0.0000(5) 0.0029(5)
C11 0.0181(6) 0.0230(7) 0.0225(6) -0.0032(5) 0.0111(5) -0.0041(5)
C12 0.0129(5) 0.0225(6) 0.0173(5) -0.0021(4) 0.0055(4) -0.0027(4)
C13 0.0170(6) 0.0227(6) 0.0232(6) 0.0004(5) 0.0080(5) -0.0010(5)
C14 0.0233(6) 0.0279(7) 0.0265(6) -0.0011(5) 0.0116(5) -0.0076(5)
C15 0.0185(6) 0.0378(8) 0.0341(7) -0.0043(6) 0.0154(5) -0.0067(5)
C16 0.0180(6) 0.0322(8) 0.0428(8) -0.0032(6) 0.0149(6) 0.0017(5)
C17 0.0184(6) 0.0220(6) 0.0328(7) 0.0005(5) 0.0111(5) 0.0003(5)
C18 0.0100(5) 0.0269(7) 0.0194(6) -0.0001(5) 0.0047(4) -0.0014(4)
C19 0.0348(7) 0.0446(9) 0.0257(7) -0.0110(6) 0.0130(6) 0.0061(6)
C20 0.0137(5) 0.0210(7) 0.0237(6) 0.0038(5) 0.0082(4) -0.0008(4)
C21 0.0124(5) 0.0189(6) 0.0200(6) 0.0034(4) 0.0071(4) -0.0013(4)
C22 0.0153(6) 0.0244(6) 0.0238(6) -0.0017(5) 0.0088(5) -0.0013(4)
C23 0.0200(6) 0.0370(8) 0.0235(6) -0.0057(5) 0.0079(5) -0.0070(5)
C24 0.0134(6) 0.0438(8) 0.0247(6) 0.0047(6) 0.0018(5) -0.0047(5)
C25 0.0143(6) 0.0284(7) 0.0350(7) 0.0101(5) 0.0074(5) 0.0034(5)
C26 0.0150(6) 0.0209(6) 0.0269(6) 0.0033(5) 0.0081(5) 0.0008(5)

_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 1.2126(14) . ?
O2 C9 1.1980(15) . ?
O3 C9 1.3275(14) . ?
O3 C10 1.4502(14) . ?
O4 C18 1.2040(15) . ?
O5 C18 1.3236(15) . ?
O5 C19 1.4550(14) . ?
N1 C11 1.1447(16) . ?
N2 C20 1.1461(16) . ?
C1 C8 1.5000(16) . ?
C1 C2 1.5325(15) . ?
C2 C7 1.5406(15) . ?
C2 C3 1.5446(15) . ?
C2 H2 1.0000 . ?
C3 C4 1.5535(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.4735(16) . ?
C4 C9 1.5428(16) . ?
C4 C5 1.5627(15) . ?
C5 C12 1.5234(15) . ?
C5 C6 1.5621(15) . ?
C5 H5 1.0000 . ?
C6 C20 1.4746(16) . ?
C6 C18 1.5380(15) . ?
C6 C7 1.5742(14) . ?
C7 C21 1.5159(15) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 C13 1.3887(16) . ?
C12 C17 1.3943(16) . ?
C13 C14 1.3936(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3798(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.3854(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.3897(17) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C26 1.3929(16) . ?
C21 C22 1.3948(16) . ?
C22 C23 1.3925(17) . ?
C22 H22 0.9500 . ?
C23 C24 1.3852(19) . ?
C23 H23 0.9500 . ?
C24 C25 1.3867(19) . ?
C24 H24 0.9500 . ?
C25 C26 1.3888(18) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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 O3 C10 115.95(10) . . ?
C18 O5 C19 115.03(10) . . ?
O1 C1 C8 122.06(10) . . ?
O1 C1 C2 121.18(10) . . ?
C8 C1 C2 116.74(10) . . ?
C1 C2 C7 112.51(9) . . ?
C1 C2 C3 107.00(9) . . ?
C7 C2 C3 109.57(9) . . ?
C1 C2 H2 109.2 . . ?
C7 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C2 C3 C4 113.31(9) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C11 C4 C9 105.89(9) . . ?
C11 C4 C3 110.91(9) . . ?
C9 C4 C3 108.12(9) . . ?
C11 C4 C5 112.07(9) . . ?
C9 C4 C5 109.54(9) . . ?
C3 C4 C5 110.15(9) . . ?
C12 C5 C6 114.57(9) . . ?
C12 C5 C4 114.23(9) . . ?
C6 C5 C4 112.08(9) . . ?
C12 C5 H5 104.9 . . ?
C6 C5 H5 104.9 . . ?
C4 C5 H5 104.9 . . ?
C20 C6 C18 106.45(9) . . ?
C20 C6 C5 115.02(9) . . ?
C18 C6 C5 107.84(9) . . ?
C20 C6 C7 108.31(9) . . ?
C18 C6 C7 110.92(9) . . ?
C5 C6 C7 108.32(9) . . ?
C21 C7 C2 116.07(9) . . ?
C21 C7 C6 112.41(9) . . ?
C2 C7 C6 107.71(9) . . ?
C21 C7 H7 106.7 . . ?
C2 C7 H7 106.7 . . ?
C6 C7 H7 106.7 . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 O3 125.26(11) . . ?
O2 C9 C4 124.26(11) . . ?
O3 C9 C4 110.47(9) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C4 178.95(14) . . ?
C13 C12 C17 118.37(10) . . ?
C13 C12 C5 123.62(10) . . ?
C17 C12 C5 118.00(10) . . ?
C12 C13 C14 120.57(11) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.44(12) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.69(11) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 119.83(12) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C12 121.09(12) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
O4 C18 O5 125.40(11) . . ?
O4 C18 C6 124.34(11) . . ?
O5 C18 C6 110.25(9) . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C6 176.25(11) . . ?
C26 C21 C22 118.47(11) . . ?
C26 C21 C7 122.56(10) . . ?
C22 C21 C7 118.95(10) . . ?
C23 C22 C21 121.15(11) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C24 C23 C22 119.78(12) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 119.48(12) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C26 120.78(12) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C21 120.32(12) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C7 17.11(15) . . . . ?
C8 C1 C2 C7 -164.51(10) . . . . ?
O1 C1 C2 C3 -103.28(12) . . . . ?
C8 C1 C2 C3 75.10(13) . . . . ?
C1 C2 C3 C4 -179.91(9) . . . . ?
C7 C2 C3 C4 57.85(12) . . . . ?
C2 C3 C4 C11 73.64(12) . . . . ?
C2 C3 C4 C9 -170.68(9) . . . . ?
C2 C3 C4 C5 -51.02(12) . . . . ?
C11 C4 C5 C12 60.31(13) . . . . ?
C9 C4 C5 C12 -56.91(12) . . . . ?
C3 C4 C5 C12 -175.71(9) . . . . ?
C11 C4 C5 C6 -72.11(12) . . . . ?
C9 C4 C5 C6 170.67(9) . . . . ?
C3 C4 C5 C6 51.87(12) . . . . ?
C12 C5 C6 C20 -69.97(12) . . . . ?
C4 C5 C6 C20 62.28(12) . . . . ?
C12 C5 C6 C18 48.61(12) . . . . ?
C4 C5 C6 C18 -179.14(9) . . . . ?
C12 C5 C6 C7 168.72(9) . . . . ?
C4 C5 C6 C7 -59.03(12) . . . . ?
C1 C2 C7 C21 51.04(13) . . . . ?
C3 C2 C7 C21 169.94(9) . . . . ?
C1 C2 C7 C6 178.04(9) . . . . ?
C3 C2 C7 C6 -63.06(11) . . . . ?
C20 C6 C7 C21 67.56(11) . . . . ?
C18 C6 C7 C21 -48.92(12) . . . . ?
C5 C6 C7 C21 -167.08(9) . . . . ?
C20 C6 C7 C2 -61.55(11) . . . . ?
C18 C6 C7 C2 -178.02(9) . . . . ?
C5 C6 C7 C2 63.81(11) . . . . ?
C10 O3 C9 O2 -1.56(16) . . . . ?
C10 O3 C9 C4 179.79(9) . . . . ?
C11 C4 C9 O2 4.98(15) . . . . ?
C3 C4 C9 O2 -113.94(12) . . . . ?
C5 C4 C9 O2 126.01(12) . . . . ?
C11 C4 C9 O3 -176.36(8) . . . . ?
C3 C4 C9 O3 64.72(11) . . . . ?
C5 C4 C9 O3 -55.32(11) . . . . ?
C9 C4 C11 N1 -25(7) . . . . ?
C3 C4 C11 N1 92(7) . . . . ?
C5 C4 C11 N1 -145(7) . . . . ?
C6 C5 C12 C13 51.88(15) . . . . ?
C4 C5 C12 C13 -79.34(14) . . . . ?
C6 C5 C12 C17 -126.78(11) . . . . ?
C4 C5 C12 C17 102.00(12) . . . . ?
C17 C12 C13 C14 0.87(17) . . . . ?
C5 C12 C13 C14 -177.78(11) . . . . ?
C12 C13 C14 C15 -1.27(18) . . . . ?
C13 C14 C15 C16 0.5(2) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C15 C16 C17 C12 -1.1(2) . . . . ?
C13 C12 C17 C16 0.31(18) . . . . ?
C5 C12 C17 C16 179.04(12) . . . . ?
C19 O5 C18 O4 1.16(16) . . . . ?
C19 O5 C18 C6 -178.49(10) . . . . ?
C20 C6 C18 O4 -1.95(15) . . . . ?
C5 C6 C18 O4 -125.88(12) . . . . ?
C7 C6 C18 O4 115.67(12) . . . . ?
C20 C6 C18 O5 177.71(9) . . . . ?
C5 C6 C18 O5 53.78(11) . . . . ?
C7 C6 C18 O5 -64.68(11) . . . . ?
C18 C6 C20 N2 118.1(19) . . . . ?
C5 C6 C20 N2 -122.5(19) . . . . ?
C7 C6 C20 N2 -1(2) . . . . ?
C2 C7 C21 C26 33.73(15) . . . . ?
C6 C7 C21 C26 -90.89(12) . . . . ?
C2 C7 C21 C22 -144.68(10) . . . . ?
C6 C7 C21 C22 90.70(12) . . . . ?
C26 C21 C22 C23 0.56(17) . . . . ?
C7 C21 C22 C23 179.04(10) . . . . ?
C21 C22 C23 C24 -0.97(18) . . . . ?
C22 C23 C24 C25 0.08(18) . . . . ?
C23 C24 C25 C26 1.22(19) . . . . ?
C24 C25 C26 C21 -1.64(18) . . . . ?
C22 C21 C26 C25 0.73(17) . . . . ?
C7 C21 C26 C25 -177.69(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        72.48
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.059

# Attachment '4a.cif'

data_m091208b
_database_code_depnum_ccdc_archive 'CCDC 782771'
#TrackingRef '4a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 N O3'
_chemical_formula_weight         345.38

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.0537(16)
_cell_length_b                   24.192(5)
_cell_length_c                   9.0943(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.02(3)
_cell_angle_gamma                90.00
_cell_volume                     1767.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    5926
_cell_measurement_theta_min      1.684
_cell_measurement_theta_max      27.863

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9745
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean 14.63
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12157
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3113
_reflns_number_gt                2743
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'

_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^)+(0.0945P)^2^+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.129(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3113
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1253
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.002
_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 0.22285(14) 0.69938(4) 0.49967(11) 0.0328(3) Uani 1 1 d . . .
O2 O 0.15127(12) 0.57235(4) 0.86145(11) 0.0282(3) Uani 1 1 d . . .
O3 O 0.38360(13) 0.57566(4) 1.01305(10) 0.0286(3) Uani 1 1 d . . .
N1 N 0.70636(16) 0.52909(5) 0.80859(14) 0.0293(3) Uani 1 1 d . . .
C1 C 0.3354(2) 0.67194(6) 0.27591(16) 0.0355(4) Uani 1 1 d . . .
H1A H 0.2576 0.6982 0.2316 0.053 Uiso 1 1 calc R . .
H1B H 0.3155 0.6363 0.2318 0.053 Uiso 1 1 calc R . .
H1C H 0.4468 0.6836 0.2605 0.053 Uiso 1 1 calc R . .
C2 C 0.31393(19) 0.66848(5) 0.43763(15) 0.0250(4) Uani 1 1 d . . .
C3 C 0.41302(18) 0.62313(5) 0.52229(15) 0.0232(3) Uani 1 1 d . . .
H3 H 0.5277 0.6227 0.4926 0.028 Uiso 1 1 calc R . .
C4 C 0.33524(18) 0.56673(6) 0.49725(15) 0.0247(4) Uani 1 1 d . . .
H4 H 0.2972 0.5538 0.4047 0.030 Uiso 1 1 calc R . .
C5 C 0.32642(18) 0.53737(5) 0.62024(15) 0.0227(4) Uani 1 1 d . . .
C6 C 0.40694(18) 0.56950(5) 0.75158(15) 0.0218(3) Uani 1 1 d . . .
C7 C 0.41370(18) 0.63045(5) 0.69047(14) 0.0221(3) Uani 1 1 d . . .
H7 H 0.3069 0.6476 0.7093 0.026 Uiso 1 1 calc R . .
C8 C 0.54676(19) 0.66568(5) 0.76945(14) 0.0234(3) Uani 1 1 d . . .
C9 C 0.5061(2) 0.69799(5) 0.88843(16) 0.0295(4) Uani 1 1 d . . .
H9 H 0.3965 0.6993 0.9142 0.035 Uiso 1 1 calc R . .
C10 C 0.6270(2) 0.72822(6) 0.96880(18) 0.0356(4) Uani 1 1 d . . .
H10 H 0.5982 0.7492 1.0488 0.043 Uiso 1 1 calc R . .
C11 C 0.7902(2) 0.72738(6) 0.93083(17) 0.0358(4) Uani 1 1 d . . .
H11 H 0.8711 0.7478 0.9849 0.043 Uiso 1 1 calc R . .
C12 C 0.8322(2) 0.69601(6) 0.81200(17) 0.0330(4) Uani 1 1 d . . .
H12 H 0.9416 0.6955 0.7853 0.040 Uiso 1 1 calc R . .
C13 C 0.71092(19) 0.66525(5) 0.73248(16) 0.0276(4) Uani 1 1 d . . .
H13 H 0.7403 0.6440 0.6531 0.033 Uiso 1 1 calc R . .
C14 C 0.31454(18) 0.57144(5) 0.89231(16) 0.0226(3) Uani 1 1 d . . .
C15 C 0.05318(19) 0.57867(6) 0.98864(16) 0.0307(4) Uani 1 1 d . . .
H15A H 0.0850 0.5508 1.0604 0.046 Uiso 1 1 calc R . .
H15B H -0.0628 0.5747 0.9583 0.046 Uiso 1 1 calc R . .
H15C H 0.0726 0.6146 1.0312 0.046 Uiso 1 1 calc R . .
C16 C 0.57571(18) 0.54748(5) 0.78787(14) 0.0224(3) Uani 1 1 d . . .
C17 C 0.26268(17) 0.48066(5) 0.63842(15) 0.0234(3) Uani 1 1 d . . .
C18 C 0.30653(18) 0.45008(5) 0.76492(16) 0.0259(4) Uani 1 1 d . . .
H18 H 0.3785 0.4654 0.8384 0.031 Uiso 1 1 calc R . .
C19 C 0.2447(2) 0.39725(6) 0.78304(18) 0.0305(4) Uani 1 1 d . . .
H19 H 0.2765 0.3772 0.8676 0.037 Uiso 1 1 calc R . .
C20 C 0.13581(19) 0.37427(6) 0.67561(17) 0.0321(4) Uani 1 1 d . . .
H20 H 0.0930 0.3390 0.6884 0.039 Uiso 1 1 calc R . .
C21 C 0.09096(18) 0.40401(6) 0.54900(17) 0.0302(4) Uani 1 1 d . . .
H21 H 0.0175 0.3887 0.4767 0.036 Uiso 1 1 calc R . .
C22 C 0.15490(18) 0.45667(6) 0.52902(16) 0.0260(4) Uani 1 1 d . . .
H22 H 0.1259 0.4760 0.4426 0.031 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 0.0368(7) 0.0301(6) 0.0316(6) 0.0026(5) 0.0033(5) 0.0085(5)
O2 0.0227(6) 0.0378(6) 0.0241(6) -0.0038(4) 0.0018(4) 0.0013(4)
O3 0.0301(6) 0.0336(6) 0.0215(6) 0.0001(4) -0.0019(5) -0.0008(4)
N1 0.0269(8) 0.0274(7) 0.0333(7) 0.0018(5) -0.0006(6) -0.0002(5)
C1 0.0485(11) 0.0311(8) 0.0261(8) 0.0011(6) -0.0025(7) 0.0030(7)
C2 0.0269(8) 0.0213(7) 0.0262(8) 0.0003(6) -0.0019(6) -0.0039(6)
C3 0.0236(8) 0.0223(7) 0.0236(8) -0.0011(5) 0.0000(6) 0.0012(6)
C4 0.0259(8) 0.0245(7) 0.0232(8) -0.0050(6) -0.0016(6) 0.0032(6)
C5 0.0208(8) 0.0218(7) 0.0250(7) -0.0027(6) -0.0012(6) 0.0041(5)
C6 0.0214(8) 0.0201(7) 0.0237(8) -0.0002(5) -0.0012(6) 0.0003(5)
C7 0.0240(8) 0.0200(7) 0.0221(7) 0.0002(6) 0.0009(6) 0.0021(5)
C8 0.0309(9) 0.0168(6) 0.0219(7) 0.0026(5) -0.0024(6) 0.0009(6)
C9 0.0378(9) 0.0230(7) 0.0275(8) -0.0018(6) 0.0014(7) 0.0001(6)
C10 0.0525(12) 0.0227(7) 0.0307(8) -0.0050(6) -0.0040(8) -0.0017(7)
C11 0.0465(11) 0.0223(7) 0.0364(9) 0.0030(6) -0.0123(8) -0.0080(7)
C12 0.0325(9) 0.0290(8) 0.0365(9) 0.0075(6) -0.0046(7) -0.0041(6)
C13 0.0310(9) 0.0241(7) 0.0273(8) 0.0015(6) -0.0001(6) -0.0009(6)
C14 0.0254(8) 0.0166(7) 0.0254(8) 0.0002(5) -0.0009(6) -0.0003(5)
C15 0.0253(9) 0.0385(8) 0.0291(8) -0.0021(6) 0.0070(7) 0.0008(6)
C16 0.0252(8) 0.0201(7) 0.0216(7) -0.0002(5) -0.0007(6) -0.0026(6)
C17 0.0207(7) 0.0211(7) 0.0285(8) -0.0043(6) 0.0040(6) 0.0026(5)
C18 0.0244(8) 0.0247(7) 0.0285(8) -0.0024(6) 0.0016(6) 0.0004(6)
C19 0.0310(9) 0.0244(7) 0.0369(9) 0.0026(6) 0.0084(7) 0.0037(6)
C20 0.0289(9) 0.0228(7) 0.0461(10) -0.0064(7) 0.0132(7) -0.0023(6)
C21 0.0224(8) 0.0284(8) 0.0404(9) -0.0116(7) 0.0048(7) -0.0024(6)
C22 0.0215(8) 0.0268(7) 0.0298(8) -0.0066(6) 0.0023(6) 0.0042(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2137(17) . ?
O2 C14 1.3253(18) . ?
O2 C15 1.4539(17) . ?
O3 C14 1.2000(18) . ?
N1 C16 1.1458(19) . ?
C1 C2 1.495(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.532(2) . ?
C3 C4 1.5119(19) . ?
C3 C7 1.5394(19) . ?
C3 H3 0.9800 . ?
C4 C5 1.3311(19) . ?
C4 H4 0.9300 . ?
C5 C17 1.4781(19) . ?
C5 C6 1.5307(19) . ?
C6 C16 1.476(2) . ?
C6 C14 1.526(2) . ?
C6 C7 1.5781(18) . ?
C7 C8 1.511(2) . ?
C7 H7 0.9800 . ?
C8 C13 1.387(2) . ?
C8 C9 1.3922(19) . ?
C9 C10 1.385(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 C18 1.392(2) . ?
C17 C22 1.400(2) . ?
C18 C19 1.386(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.391(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

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
C14 O2 C15 114.81(11) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 122.55(13) . . ?
O1 C2 C3 121.19(13) . . ?
C1 C2 C3 116.26(12) . . ?
C4 C3 C2 112.02(12) . . ?
C4 C3 C7 103.07(11) . . ?
C2 C3 C7 112.47(11) . . ?
C4 C3 H3 109.7 . . ?
C2 C3 H3 109.7 . . ?
C7 C3 H3 109.7 . . ?
C5 C4 C3 113.64(12) . . ?
C5 C4 H4 123.2 . . ?
C3 C4 H4 123.2 . . ?
C4 C5 C17 128.96(12) . . ?
C4 C5 C6 109.88(12) . . ?
C17 C5 C6 121.03(11) . . ?
C16 C6 C14 108.62(12) . . ?
C16 C6 C5 108.93(11) . . ?
C14 C6 C5 117.73(12) . . ?
C16 C6 C7 111.23(11) . . ?
C14 C6 C7 107.31(10) . . ?
C5 C6 C7 102.88(11) . . ?
C8 C7 C3 119.36(12) . . ?
C8 C7 C6 113.61(11) . . ?
C3 C7 C6 104.15(10) . . ?
C8 C7 H7 106.3 . . ?
C3 C7 H7 106.3 . . ?
C6 C7 H7 106.3 . . ?
C13 C8 C9 118.20(14) . . ?
C13 C8 C7 122.48(12) . . ?
C9 C8 C7 119.25(14) . . ?
C10 C9 C8 120.80(15) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 120.39(14) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.54(15) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 119.92(16) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 121.14(14) . . ?
C8 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
O3 C14 O2 125.57(14) . . ?
O3 C14 C6 123.25(13) . . ?
O2 C14 C6 110.97(12) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C6 176.27(14) . . ?
C18 C17 C22 118.41(12) . . ?
C18 C17 C5 121.04(12) . . ?
C22 C17 C5 120.55(12) . . ?
C19 C18 C17 121.06(14) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 120.14(14) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.63(13) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C22 120.49(14) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 120.26(13) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 102.68(16) . . . . ?
C1 C2 C3 C4 -76.92(16) . . . . ?
O1 C2 C3 C7 -12.86(19) . . . . ?
C1 C2 C3 C7 167.54(12) . . . . ?
C2 C3 C4 C5 -134.71(13) . . . . ?
C7 C3 C4 C5 -13.57(16) . . . . ?
C3 C4 C5 C17 -178.39(13) . . . . ?
C3 C4 C5 C6 -2.62(17) . . . . ?
C4 C5 C6 C16 -100.87(13) . . . . ?
C17 C5 C6 C16 75.30(16) . . . . ?
C4 C5 C6 C14 134.96(13) . . . . ?
C17 C5 C6 C14 -48.87(17) . . . . ?
C4 C5 C6 C7 17.25(15) . . . . ?
C17 C5 C6 C7 -166.59(12) . . . . ?
C4 C3 C7 C8 150.98(12) . . . . ?
C2 C3 C7 C8 -88.19(15) . . . . ?
C4 C3 C7 C6 22.97(14) . . . . ?
C2 C3 C7 C6 143.80(11) . . . . ?
C16 C6 C7 C8 -39.48(16) . . . . ?
C14 C6 C7 C8 79.20(14) . . . . ?
C5 C6 C7 C8 -155.96(12) . . . . ?
C16 C6 C7 C3 91.98(13) . . . . ?
C14 C6 C7 C3 -149.34(11) . . . . ?
C5 C6 C7 C3 -24.50(14) . . . . ?
C3 C7 C8 C13 -39.42(18) . . . . ?
C6 C7 C8 C13 84.08(16) . . . . ?
C3 C7 C8 C9 143.67(13) . . . . ?
C6 C7 C8 C9 -92.82(15) . . . . ?
C13 C8 C9 C10 -0.9(2) . . . . ?
C7 C8 C9 C10 176.14(12) . . . . ?
C8 C9 C10 C11 0.9(2) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C9 C8 C13 C12 0.2(2) . . . . ?
C7 C8 C13 C12 -176.71(12) . . . . ?
C11 C12 C13 C8 0.5(2) . . . . ?
C15 O2 C14 O3 -0.49(19) . . . . ?
C15 O2 C14 C6 -175.31(11) . . . . ?
C16 C6 C14 O3 26.44(17) . . . . ?
C5 C6 C14 O3 150.77(13) . . . . ?
C7 C6 C14 O3 -93.91(15) . . . . ?
C16 C6 C14 O2 -158.59(11) . . . . ?
C5 C6 C14 O2 -34.26(15) . . . . ?
C7 C6 C14 O2 81.06(13) . . . . ?
C14 C6 C16 N1 147(2) . . . . ?
C5 C6 C16 N1 18(2) . . . . ?
C7 C6 C16 N1 -95(2) . . . . ?
C4 C5 C17 C18 160.56(15) . . . . ?
C6 C5 C17 C18 -14.80(19) . . . . ?
C4 C5 C17 C22 -20.2(2) . . . . ?
C6 C5 C17 C22 164.46(13) . . . . ?
C22 C17 C18 C19 -0.3(2) . . . . ?
C5 C17 C18 C19 178.96(13) . . . . ?
C17 C18 C19 C20 -0.9(2) . . . . ?
C18 C19 C20 C21 1.0(2) . . . . ?
C19 C20 C21 C22 0.2(2) . . . . ?
C20 C21 C22 C17 -1.4(2) . . . . ?
C18 C17 C22 C21 1.4(2) . . . . ?
C5 C17 C22 C21 -177.83(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.071