# 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

_publ_contact_author_name        'Prof Dr Fushun Liang'
_publ_contact_author_email       liangfs112@nenu.edu.cn
loop_
_publ_author_name
'Shaoxia Lin'
'Ying Wei'
'Fushun Liang'
'Baozhong Zhao'
'Yanling Liu'
'Penjiu Liu'

#Northeast Normal University
#Changchun
#Jilin
#130024
#P. R. China

data_100707-lfs01-gj
_database_code_depnum_ccdc_archive 'CCDC 796156'
#TrackingRef 'linsx3.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 N3 O2'
_chemical_formula_weight         411.49

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   13.710(5)
_cell_length_b                   13.748(5)
_cell_length_c                   11.855(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 100.854(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2194.5(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9958
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.1031
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         29.22
_reflns_number_total             5063
_reflns_number_gt                1966
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0377P)^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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5063
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   0.858
_refine_ls_restrained_S_all      0.858
_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
C1 C 0.87530(12) 0.52423(13) 0.27671(15) 0.0427(5) Uani 1 1 d . . .
C2 C 0.93812(14) 0.60337(14) 0.28976(17) 0.0520(5) Uani 1 1 d . . .
H2 H 0.9579 0.6312 0.3619 0.062 Uiso 1 1 calc R . .
C3 C 0.97180(15) 0.64144(15) 0.1968(2) 0.0642(6) Uani 1 1 d . . .
H3 H 1.0134 0.6955 0.2059 0.077 Uiso 1 1 calc R . .
C4 C 0.94383(17) 0.5994(2) 0.0906(2) 0.0759(7) Uani 1 1 d . . .
H4 H 0.9668 0.6246 0.0276 0.091 Uiso 1 1 calc R . .
C5 C 0.88202(18) 0.5204(2) 0.07744(18) 0.0795(7) Uani 1 1 d . . .
H5 H 0.8635 0.4919 0.0054 0.095 Uiso 1 1 calc R . .
C6 C 0.84692(14) 0.48263(15) 0.16966(17) 0.0608(6) Uani 1 1 d . . .
H6 H 0.8043 0.4294 0.1599 0.073 Uiso 1 1 calc R . .
C7 C 0.75534(12) 0.54933(12) 0.40526(14) 0.0404(4) Uani 1 1 d . . .
H7 H 0.7715 0.6170 0.3902 0.048 Uiso 1 1 calc R . .
C8 C 0.65733(13) 0.52834(13) 0.32604(14) 0.0442(5) Uani 1 1 d . . .
C9 C 0.60009(15) 0.60475(15) 0.27647(17) 0.0647(6) Uani 1 1 d . . .
H9 H 0.6218 0.6681 0.2932 0.078 Uiso 1 1 calc R . .
C10 C 0.51017(17) 0.5891(2) 0.20169(19) 0.0822(7) Uani 1 1 d . . .
H10 H 0.4722 0.6424 0.1716 0.099 Uiso 1 1 calc R . .
C11 C 0.47642(16) 0.4976(2) 0.17140(17) 0.0705(7) Uani 1 1 d . . .
C12 C 0.38035(17) 0.4830(2) 0.0862(2) 0.1100(10) Uani 1 1 d . . .
H12A H 0.3522 0.5451 0.0617 0.165 Uiso 1 1 calc R . .
H12B H 0.3345 0.4470 0.1221 0.165 Uiso 1 1 calc R . .
H12C H 0.3935 0.4475 0.0210 0.165 Uiso 1 1 calc R . .
C13 C 0.53288(17) 0.42194(17) 0.22116(19) 0.0732(7) Uani 1 1 d . . .
H13 H 0.5110 0.3587 0.2037 0.088 Uiso 1 1 calc R . .
C14 C 0.62184(15) 0.43614(15) 0.29698(17) 0.0647(6) Uani 1 1 d . . .
H14 H 0.6582 0.3825 0.3288 0.078 Uiso 1 1 calc R . .
C15 C 0.85659(14) 0.39715(14) 0.41528(16) 0.0465(5) Uani 1 1 d . . .
C16 C 0.81234(14) 0.37177(13) 0.51265(17) 0.0491(5) Uani 1 1 d . . .
C17 C 0.81172(17) 0.27464(14) 0.57026(19) 0.0713(7) Uani 1 1 d . . .
H17A H 0.8786 0.2506 0.5971 0.086 Uiso 1 1 calc R . .
H17B H 0.7742 0.2269 0.5195 0.086 Uiso 1 1 calc R . .
C18 C 0.76047(17) 0.29980(16) 0.6703(2) 0.0786(7) Uani 1 1 d . . .
H18A H 0.6999 0.2623 0.6653 0.094 Uiso 1 1 calc R . .
H18B H 0.8038 0.2850 0.7428 0.094 Uiso 1 1 calc R . .
C19 C 0.76929(14) 0.43750(14) 0.56851(16) 0.0480(5) Uani 1 1 d . . .
C20 C 0.75739(13) 0.54304(13) 0.53744(14) 0.0438(5) Uani 1 1 d . . .
C21 C 0.66066(14) 0.58199(14) 0.56787(16) 0.0570(5) Uani 1 1 d . . .
H21A H 0.6054 0.5465 0.5232 0.068 Uiso 1 1 calc R . .
H21B H 0.6612 0.5685 0.6483 0.068 Uiso 1 1 calc R . .
C22 C 0.64302(15) 0.68839(15) 0.54744(19) 0.0676(6) Uani 1 1 d . . .
H22A H 0.6752 0.7245 0.6145 0.081 Uiso 1 1 calc R . .
H22B H 0.6720 0.7088 0.4827 0.081 Uiso 1 1 calc R . .
C23 C 0.5347(2) 0.71075(18) 0.52365(19) 0.0790(7) Uani 1 1 d . . .
C24 C 0.85133(13) 0.59960(14) 0.59724(14) 0.0510(5) Uani 1 1 d . . .
H24A H 0.9071 0.5777 0.5642 0.061 Uiso 1 1 calc R . .
H24B H 0.8412 0.6679 0.5783 0.061 Uiso 1 1 calc R . .
C25 C 0.88068(14) 0.59106(14) 0.72781(15) 0.0573(5) Uani 1 1 d . . .
H25A H 0.8729 0.5239 0.7494 0.069 Uiso 1 1 calc R . .
H25B H 0.9504 0.6076 0.7504 0.069 Uiso 1 1 calc R . .
C26 C 0.82374(16) 0.65232(15) 0.79121(17) 0.0538(5) Uani 1 1 d . . .
O1 O 0.91152(10) 0.34206(9) 0.37338(12) 0.0618(4) Uani 1 1 d . . .
O2 O 0.73766(10) 0.40462(10) 0.66271(11) 0.0671(4) Uani 1 1 d . . .
N1 N 0.83653(10) 0.48968(10) 0.37383(12) 0.0420(4) Uani 1 1 d . . .
N2 N 0.78045(15) 0.70129(13) 0.84068(15) 0.0732(6) Uani 1 1 d . . .
N3 N 0.45167(16) 0.72516(17) 0.5042(2) 0.1044(8) Uani 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
C1 0.0357(10) 0.0477(11) 0.0458(12) -0.0017(10) 0.0105(9) 0.0046(9)
C2 0.0503(12) 0.0537(12) 0.0542(12) 0.0017(10) 0.0157(10) 0.0007(10)
C3 0.0551(13) 0.0661(14) 0.0735(16) 0.0129(13) 0.0178(12) -0.0017(11)
C4 0.0601(16) 0.111(2) 0.0606(16) 0.0293(15) 0.0217(12) 0.0129(15)
C5 0.0704(16) 0.127(2) 0.0414(13) -0.0059(14) 0.0098(12) 0.0003(16)
C6 0.0540(13) 0.0768(15) 0.0509(13) -0.0091(12) 0.0079(11) -0.0048(11)
C7 0.0382(11) 0.0392(10) 0.0453(11) 0.0019(9) 0.0118(9) 0.0038(8)
C8 0.0436(11) 0.0501(12) 0.0402(10) 0.0010(9) 0.0112(9) 0.0027(10)
C9 0.0617(14) 0.0628(14) 0.0646(13) 0.0103(11) -0.0006(12) -0.0017(11)
C10 0.0611(16) 0.103(2) 0.0746(16) 0.0302(15) -0.0069(13) 0.0071(14)
C11 0.0532(14) 0.106(2) 0.0506(13) 0.0078(14) 0.0052(11) -0.0175(14)
C12 0.0670(17) 0.175(3) 0.0767(17) 0.0225(18) -0.0150(14) -0.0321(17)
C13 0.0673(16) 0.0813(17) 0.0675(14) -0.0094(13) 0.0037(13) -0.0212(14)
C14 0.0567(14) 0.0635(15) 0.0694(15) -0.0062(11) 0.0003(12) -0.0004(11)
C15 0.0424(12) 0.0403(12) 0.0543(12) -0.0034(10) 0.0028(10) -0.0003(9)
C16 0.0469(12) 0.0445(12) 0.0551(12) 0.0099(10) 0.0076(10) -0.0001(9)
C17 0.0761(16) 0.0548(14) 0.0788(16) 0.0195(12) 0.0036(13) -0.0043(12)
C18 0.0744(16) 0.0722(17) 0.0852(17) 0.0364(14) 0.0046(14) -0.0070(12)
C19 0.0429(11) 0.0569(13) 0.0433(12) 0.0074(10) 0.0057(9) -0.0075(10)
C20 0.0389(11) 0.0525(12) 0.0410(11) -0.0010(9) 0.0101(8) 0.0022(9)
C21 0.0549(13) 0.0688(15) 0.0486(12) 0.0009(10) 0.0131(10) 0.0076(11)
C22 0.0614(15) 0.0753(16) 0.0676(14) -0.0024(12) 0.0158(11) 0.0056(11)
C23 0.0767(19) 0.0889(18) 0.0698(16) -0.0012(13) 0.0095(14) 0.0238(14)
C24 0.0448(11) 0.0582(12) 0.0507(12) -0.0072(10) 0.0104(9) -0.0004(10)
C25 0.0539(13) 0.0620(13) 0.0526(12) -0.0084(11) 0.0015(10) 0.0093(10)
C26 0.0653(14) 0.0499(13) 0.0437(12) -0.0021(10) 0.0043(11) -0.0004(11)
O1 0.0599(9) 0.0481(8) 0.0788(10) -0.0061(7) 0.0170(8) 0.0126(7)
O2 0.0732(10) 0.0742(10) 0.0572(9) 0.0180(8) 0.0203(7) -0.0037(8)
N1 0.0428(9) 0.0398(9) 0.0458(9) -0.0004(7) 0.0147(7) 0.0021(7)
N2 0.0926(15) 0.0659(13) 0.0639(12) -0.0074(10) 0.0218(11) 0.0067(11)
N3 0.0601(14) 0.1226(19) 0.1227(18) -0.0064(15) -0.0028(13) 0.0277(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
C1 C6 1.380(2) . ?
C1 C2 1.378(2) . ?
C1 N1 1.437(2) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.485(2) . ?
C7 C8 1.515(2) . ?
C7 C20 1.564(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.375(2) . ?
C8 C14 1.378(2) . ?
C9 C10 1.393(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(3) . ?
C10 H10 0.9300 . ?
C11 C13 1.363(3) . ?
C11 C12 1.515(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O1 1.236(2) . ?
C15 N1 1.373(2) . ?
C15 C16 1.444(3) . ?
C16 C19 1.323(2) . ?
C16 C17 1.501(3) . ?
C17 C18 1.528(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 O2 1.474(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 O2 1.350(2) . ?
C19 C20 1.498(3) . ?
C20 C21 1.535(3) . ?
C20 C24 1.556(2) . ?
C21 C22 1.495(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.491(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 N3 1.135(3) . ?
C24 C25 1.529(2) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.451(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 N2 1.131(2) . ?

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
C6 C1 C2 119.51(18) . . ?
C6 C1 N1 121.16(17) . . ?
C2 C1 N1 119.26(15) . . ?
C3 C2 C1 120.48(18) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N1 C7 C8 111.00(13) . . ?
N1 C7 C20 110.35(13) . . ?
C8 C7 C20 117.19(14) . . ?
N1 C7 H7 105.8 . . ?
C8 C7 H7 105.8 . . ?
C20 C7 H7 105.8 . . ?
C9 C8 C14 116.71(17) . . ?
C9 C8 C7 119.18(16) . . ?
C14 C8 C7 124.08(17) . . ?
C8 C9 C10 121.3(2) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 121.7(2) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C13 C11 C10 116.93(19) . . ?
C13 C11 C12 122.6(2) . . ?
C10 C11 C12 120.5(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 122.1(2) . . ?
C11 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C8 C14 C13 121.19(19) . . ?
C8 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
O1 C15 N1 121.33(18) . . ?
O1 C15 C16 123.54(18) . . ?
N1 C15 C16 115.08(17) . . ?
C19 C16 C15 121.95(17) . . ?
C19 C16 C17 109.80(19) . . ?
C15 C16 C17 128.17(19) . . ?
C16 C17 C18 101.22(18) . . ?
C16 C17 H17A 111.5 . . ?
C18 C17 H17A 111.5 . . ?
C16 C17 H17B 111.5 . . ?
C18 C17 H17B 111.5 . . ?
H17A C17 H17B 109.3 . . ?
O2 C18 C17 107.30(16) . . ?
O2 C18 H18A 110.3 . . ?
C17 C18 H18A 110.3 . . ?
O2 C18 H18B 110.3 . . ?
C17 C18 H18B 110.3 . . ?
H18A C18 H18B 108.5 . . ?
C16 C19 O2 115.37(17) . . ?
C16 C19 C20 125.20(18) . . ?
O2 C19 C20 119.39(18) . . ?
C19 C20 C21 109.81(16) . . ?
C19 C20 C24 109.23(14) . . ?
C21 C20 C24 113.34(15) . . ?
C19 C20 C7 106.28(14) . . ?
C21 C20 C7 111.27(14) . . ?
C24 C20 C7 106.62(14) . . ?
C22 C21 C20 115.08(17) . . ?
C22 C21 H21A 108.5 . . ?
C20 C21 H21A 108.5 . . ?
C22 C21 H21B 108.5 . . ?
C20 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C23 C22 C21 110.95(18) . . ?
C23 C22 H22A 109.4 . . ?
C21 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
N3 C23 C22 178.0(3) . . ?
C25 C24 C20 117.41(16) . . ?
C25 C24 H24A 108.0 . . ?
C20 C24 H24A 108.0 . . ?
C25 C24 H24B 108.0 . . ?
C20 C24 H24B 108.0 . . ?
H24A C24 H24B 107.2 . . ?
C26 C25 C24 114.54(16) . . ?
C26 C25 H25A 108.6 . . ?
C24 C25 H25A 108.6 . . ?
C26 C25 H25B 108.6 . . ?
C24 C25 H25B 108.6 . . ?
H25A C25 H25B 107.6 . . ?
N2 C26 C25 178.9(2) . . ?
C19 O2 C18 106.28(16) . . ?
C15 N1 C1 120.92(15) . . ?
C15 N1 C7 122.07(15) . . ?
C1 N1 C7 115.23(14) . . ?

_diffrn_measured_fraction_theta_max 0.850
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.034