# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
'Yue Wang'
'Yan Fan'
'Feng Li'
'Xiaoyue Mu'
'Weifeng Song'
'Hongyu Zhang'
;
Tianlei Zhou
;
_publ_contact_author_name        'Yue Wang'
_publ_contact_author_email       YUEWANG@JLU.EDU.CN

data_1
_database_code_depnum_ccdc_archive 'CCDC 709893'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 N O2'
_chemical_formula_weight         213.23

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                   8.0800(16)
_cell_length_b                   9.812(2)
_cell_length_c                   14.043(3)
_cell_angle_alpha                85.96(3)
_cell_angle_beta                 88.64(3)
_cell_angle_gamma                73.45(3)
_cell_volume                     1064.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5795
_cell_measurement_theta_min      3
_cell_measurement_theta_max      27.51

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9498
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_process_details   
;
Higash,T(1995) Progrom for Absorption Correcttion.
Rigaku Corporation,Tokyo,Japan.
;
_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  'Omega scan'
_diffrn_measurement_method       10.0
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            10269
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0648
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4775
_reflns_number_gt                2349
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0907P)^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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4775
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1621
_refine_ls_wR_factor_gt          0.1337
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_restrained_S_all      0.907
_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 0.3611(3) -0.0496(2) 0.92694(14) 0.0510(5) Uani 1 1 d . . .
C2 C 0.2691(3) 0.08060(19) 0.87025(14) 0.0475(5) Uani 1 1 d . . .
C3 C 0.1000(3) 0.1524(2) 0.89527(16) 0.0594(6) Uani 1 1 d . . .
H3 H 0.0474 0.1156 0.9465 0.071 Uiso 1 1 calc R . .
C4 C 0.0097(3) 0.2757(2) 0.84605(17) 0.0649(6) Uani 1 1 d . . .
H4 H -0.1030 0.3221 0.8634 0.078 Uiso 1 1 calc R . .
C5 C 0.0887(3) 0.3301(2) 0.77014(16) 0.0610(6) Uani 1 1 d . . .
H5 H 0.0286 0.4142 0.7368 0.073 Uiso 1 1 calc R . .
C6 C 0.2529(3) 0.26279(19) 0.74339(15) 0.0530(5) Uani 1 1 d . . .
H6 H 0.3026 0.3016 0.6918 0.064 Uiso 1 1 calc R . .
C7 C 0.3492(3) 0.13571(19) 0.79203(13) 0.0467(5) Uani 1 1 d . . .
C8 C 0.6083(3) 0.10084(18) 0.68687(14) 0.0475(5) Uani 1 1 d . . .
C9 C 0.7753(3) 0.10473(19) 0.69771(16) 0.0548(5) Uani 1 1 d . . .
H9 H 0.8221 0.0949 0.7585 0.066 Uiso 1 1 calc R . .
C10 C 0.8743(3) 0.1231(2) 0.61903(18) 0.0638(6) Uani 1 1 d . . .
H10 H 0.9881 0.1234 0.6271 0.077 Uiso 1 1 calc R . .
C11 C 0.8057(3) 0.1409(2) 0.52872(18) 0.0654(6) Uani 1 1 d . . .
H11 H 0.8723 0.1535 0.4757 0.078 Uiso 1 1 calc R . .
C12 C 0.6381(3) 0.1397(2) 0.51791(16) 0.0639(6) Uani 1 1 d . . .
H12 H 0.5903 0.1533 0.4571 0.077 Uiso 1 1 calc R . .
C13 C 0.5395(3) 0.11885(19) 0.59567(15) 0.0564(5) Uani 1 1 d . . .
H13 H 0.4265 0.1168 0.5872 0.068 Uiso 1 1 calc R . .
C14 C 0.5998(3) 0.5944(2) 0.06721(14) 0.0509(5) Uani 1 1 d . . .
C15 C 0.6898(3) 0.4617(2) 0.12131(13) 0.0484(5) Uani 1 1 d . . .
C16 C 0.6137(3) 0.4104(2) 0.20186(14) 0.0510(5) Uani 1 1 d . . .
C17 C 0.7093(3) 0.2824(2) 0.24936(16) 0.0653(6) Uani 1 1 d . . .
H17 H 0.6616 0.2452 0.3024 0.078 Uiso 1 1 calc R . .
C18 C 0.8707(3) 0.2114(2) 0.21928(18) 0.0726(7) Uani 1 1 d . . .
H18 H 0.9310 0.1269 0.2522 0.087 Uiso 1 1 calc R . .
C19 C 0.9457(3) 0.2631(2) 0.14071(18) 0.0711(7) Uani 1 1 d . . .
H19 H 1.0562 0.2146 0.1209 0.085 Uiso 1 1 calc R . .
C20 C 0.8552(3) 0.3865(2) 0.09274(16) 0.0596(6) Uani 1 1 d . . .
H20 H 0.9050 0.4214 0.0396 0.071 Uiso 1 1 calc R . .
C21 C 0.3664(3) 0.4333(2) 0.31210(15) 0.0522(5) Uani 1 1 d . . .
C22 C 0.3008(3) 0.3199(2) 0.30522(17) 0.0691(6) Uani 1 1 d . . .
H22 H 0.3174 0.2716 0.2495 0.083 Uiso 1 1 calc R . .
C23 C 0.2107(3) 0.2772(2) 0.38031(19) 0.0728(7) Uani 1 1 d . . .
H23 H 0.1679 0.1994 0.3755 0.087 Uiso 1 1 calc R . .
C24 C 0.1838(3) 0.3486(2) 0.46196(18) 0.0668(6) Uani 1 1 d . . .
H24 H 0.1214 0.3206 0.5123 0.080 Uiso 1 1 calc R . .
C25 C 0.2491(3) 0.4612(2) 0.46913(17) 0.0679(6) Uani 1 1 d . . .
H25 H 0.2309 0.5100 0.5246 0.082 Uiso 1 1 calc R . .
C26 C 0.3418(3) 0.5034(2) 0.39479(16) 0.0615(6) Uani 1 1 d . . .
H26 H 0.3877 0.5792 0.4007 0.074 Uiso 1 1 calc R . .
N1 N 0.5160(2) 0.07050(17) 0.76765(12) 0.0585(5) Uani 1 1 d . . .
H1 H 0.5717 0.0022 0.8067 0.070 Uiso 1 1 calc R . .
N2 N 0.4549(2) 0.48152(19) 0.23424(13) 0.0692(6) Uani 1 1 d . . .
H2 H 0.4039 0.5622 0.2052 0.083 Uiso 1 1 calc R . .
O1 O 0.5118(2) -0.11791(14) 0.91174(10) 0.0610(4) Uani 1 1 d . . .
O2 O 0.2714(2) -0.08921(16) 0.99753(11) 0.0680(4) Uani 1 1 d . . .
H2A H 0.3312 -0.1617 1.0260 0.102 Uiso 1 1 calc R . .
O3 O 0.4560(2) 0.67069(15) 0.08887(11) 0.0638(4) Uani 1 1 d . . .
O4 O 0.6842(2) 0.62850(16) -0.00755(11) 0.0695(5) Uani 1 1 d . . .
H4A H 0.6302 0.7068 -0.0314 0.104 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
C1 0.0534(14) 0.0566(12) 0.0461(13) 0.0009(9) 0.0021(10) -0.0217(10)
C2 0.0466(12) 0.0539(11) 0.0446(11) -0.0007(8) 0.0016(9) -0.0193(9)
C3 0.0522(14) 0.0738(14) 0.0540(14) -0.0043(10) 0.0044(11) -0.0215(11)
C4 0.0439(13) 0.0769(15) 0.0692(16) -0.0072(12) 0.0016(11) -0.0091(11)
C5 0.0546(14) 0.0554(12) 0.0655(15) 0.0003(10) -0.0082(11) -0.0037(10)
C6 0.0526(13) 0.0510(11) 0.0525(13) 0.0026(9) 0.0015(10) -0.0114(9)
C7 0.0454(12) 0.0482(10) 0.0463(12) -0.0013(8) 0.0007(9) -0.0133(9)
C8 0.0478(12) 0.0393(9) 0.0498(12) 0.0068(8) 0.0067(9) -0.0063(8)
C9 0.0486(13) 0.0517(11) 0.0588(14) 0.0023(9) 0.0000(10) -0.0074(9)
C10 0.0460(13) 0.0593(13) 0.0832(18) -0.0017(11) 0.0109(12) -0.0117(10)
C11 0.0694(17) 0.0579(13) 0.0633(16) 0.0039(10) 0.0233(13) -0.0129(11)
C12 0.0745(17) 0.0649(13) 0.0495(14) 0.0023(10) 0.0067(12) -0.0171(12)
C13 0.0541(13) 0.0566(12) 0.0574(14) 0.0046(9) 0.0018(11) -0.0161(10)
C14 0.0573(14) 0.0581(12) 0.0417(12) 0.0008(9) 0.0011(10) -0.0242(10)
C15 0.0511(13) 0.0562(11) 0.0397(11) -0.0009(8) -0.0006(9) -0.0188(9)
C16 0.0469(13) 0.0547(11) 0.0473(12) 0.0021(9) 0.0004(10) -0.0090(9)
C17 0.0566(15) 0.0706(13) 0.0557(14) 0.0156(10) 0.0034(11) -0.0021(11)
C18 0.0601(16) 0.0725(15) 0.0700(17) 0.0132(11) -0.0020(13) 0.0016(12)
C19 0.0559(15) 0.0761(15) 0.0715(17) -0.0031(12) 0.0077(12) -0.0041(12)
C20 0.0553(14) 0.0693(14) 0.0545(14) -0.0059(10) 0.0080(11) -0.0185(11)
C21 0.0472(12) 0.0484(11) 0.0512(13) 0.0117(9) 0.0068(9) -0.0019(9)
C22 0.0754(17) 0.0664(14) 0.0664(16) -0.0091(11) 0.0083(13) -0.0213(12)
C23 0.0681(17) 0.0665(14) 0.0880(19) 0.0022(12) 0.0093(14) -0.0284(12)
C24 0.0517(14) 0.0710(14) 0.0696(17) 0.0171(12) 0.0165(12) -0.0110(11)
C25 0.0712(17) 0.0689(14) 0.0566(14) -0.0047(11) 0.0146(12) -0.0095(12)
C26 0.0624(15) 0.0483(11) 0.0704(16) 0.0007(10) 0.0079(12) -0.0121(10)
N1 0.0493(11) 0.0597(10) 0.0556(11) 0.0182(8) 0.0083(9) -0.0039(8)
N2 0.0584(12) 0.0652(11) 0.0661(13) 0.0260(9) 0.0177(10) 0.0026(9)
O1 0.0560(10) 0.0625(9) 0.0580(10) 0.0144(7) 0.0070(7) -0.0111(7)
O2 0.0601(10) 0.0773(10) 0.0641(10) 0.0191(8) 0.0106(8) -0.0222(8)
O3 0.0576(10) 0.0660(9) 0.0616(10) 0.0175(7) 0.0049(8) -0.0131(8)
O4 0.0760(12) 0.0692(10) 0.0574(10) 0.0152(7) 0.0152(9) -0.0172(8)

_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 O1 1.233(2) . ?
C1 O2 1.316(2) . ?
C1 C2 1.471(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.414(3) . ?
C3 C4 1.370(3) . ?
C4 C5 1.382(3) . ?
C5 C6 1.360(3) . ?
C6 C7 1.407(3) . ?
C7 N1 1.365(3) . ?
C8 C9 1.373(3) . ?
C8 C13 1.388(3) . ?
C8 N1 1.404(2) . ?
C9 C10 1.380(3) . ?
C10 C11 1.376(3) . ?
C11 C12 1.370(3) . ?
C12 C13 1.374(3) . ?
C14 O3 1.234(2) . ?
C14 O4 1.314(2) . ?
C14 C15 1.466(3) . ?
C15 C20 1.395(3) . ?
C15 C16 1.405(3) . ?
C16 N2 1.359(3) . ?
C16 C17 1.405(3) . ?
C17 C18 1.365(3) . ?
C18 C19 1.381(3) . ?
C19 C20 1.363(3) . ?
C21 C26 1.372(3) . ?
C21 C22 1.372(3) . ?
C21 N2 1.418(2) . ?
C22 C23 1.376(3) . ?
C23 C24 1.367(3) . ?
C24 C25 1.364(3) . ?
C25 C26 1.379(3) . ?

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
O1 C1 O2 121.14(19) . . ?
O1 C1 C2 123.77(18) . . ?
O2 C1 C2 115.08(19) . . ?
C3 C2 C7 119.42(19) . . ?
C3 C2 C1 119.20(19) . . ?
C7 C2 C1 121.38(18) . . ?
C4 C3 C2 121.6(2) . . ?
C3 C4 C5 118.9(2) . . ?
C6 C5 C4 121.2(2) . . ?
C5 C6 C7 121.4(2) . . ?
N1 C7 C6 121.63(18) . . ?
N1 C7 C2 120.81(18) . . ?
C6 C7 C2 117.50(18) . . ?
C9 C8 C13 118.90(19) . . ?
C9 C8 N1 119.0(2) . . ?
C13 C8 N1 122.0(2) . . ?
C8 C9 C10 120.5(2) . . ?
C11 C10 C9 120.4(2) . . ?
C12 C11 C10 119.1(2) . . ?
C11 C12 C13 120.9(2) . . ?
C12 C13 C8 120.1(2) . . ?
O3 C14 O4 121.24(19) . . ?
O3 C14 C15 123.80(19) . . ?
O4 C14 C15 115.0(2) . . ?
C20 C15 C16 119.63(19) . . ?
C20 C15 C14 119.09(19) . . ?
C16 C15 C14 121.27(19) . . ?
N2 C16 C17 120.58(19) . . ?
N2 C16 C15 122.01(18) . . ?
C17 C16 C15 117.41(19) . . ?
C18 C17 C16 121.4(2) . . ?
C17 C18 C19 121.0(2) . . ?
C20 C19 C18 118.9(2) . . ?
C19 C20 C15 121.7(2) . . ?
C26 C21 C22 119.31(19) . . ?
C26 C21 N2 119.7(2) . . ?
C22 C21 N2 121.0(2) . . ?
C21 C22 C23 120.3(2) . . ?
C24 C23 C22 120.3(2) . . ?
C25 C24 C23 119.6(2) . . ?
C24 C25 C26 120.5(2) . . ?
C21 C26 C25 120.0(2) . . ?
C7 N1 C8 128.15(17) . . ?
C16 N2 C21 125.25(17) . . ?

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 C3 -178.07(19) . . . . ?
O2 C1 C2 C3 1.2(3) . . . . ?
O1 C1 C2 C7 0.9(3) . . . . ?
O2 C1 C2 C7 -179.88(18) . . . . ?
C7 C2 C3 C4 -0.3(3) . . . . ?
C1 C2 C3 C4 178.65(19) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 N1 -177.61(19) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
C3 C2 C7 N1 177.94(18) . . . . ?
C1 C2 C7 N1 -1.0(3) . . . . ?
C3 C2 C7 C6 0.6(3) . . . . ?
C1 C2 C7 C6 -178.38(17) . . . . ?
C13 C8 C9 C10 -1.4(3) . . . . ?
N1 C8 C9 C10 174.87(17) . . . . ?
C8 C9 C10 C11 1.4(3) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
C11 C12 C13 C8 1.1(3) . . . . ?
C9 C8 C13 C12 0.2(3) . . . . ?
N1 C8 C13 C12 -175.98(17) . . . . ?
O3 C14 C15 C20 -177.4(2) . . . . ?
O4 C14 C15 C20 2.2(3) . . . . ?
O3 C14 C15 C16 1.6(3) . . . . ?
O4 C14 C15 C16 -178.69(19) . . . . ?
C20 C15 C16 N2 178.2(2) . . . . ?
C14 C15 C16 N2 -0.9(3) . . . . ?
C20 C15 C16 C17 -0.9(3) . . . . ?
C14 C15 C16 C17 179.99(19) . . . . ?
N2 C16 C17 C18 -178.4(2) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C17 C18 C19 C20 -0.5(4) . . . . ?
C18 C19 C20 C15 0.4(4) . . . . ?
C16 C15 C20 C19 0.4(3) . . . . ?
C14 C15 C20 C19 179.5(2) . . . . ?
C26 C21 C22 C23 0.3(4) . . . . ?
N2 C21 C22 C23 -178.0(2) . . . . ?
C21 C22 C23 C24 0.9(4) . . . . ?
C22 C23 C24 C25 -1.0(4) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
C22 C21 C26 C25 -1.3(3) . . . . ?
N2 C21 C26 C25 177.0(2) . . . . ?
C24 C25 C26 C21 1.1(4) . . . . ?
C6 C7 N1 C8 -10.6(3) . . . . ?
C2 C7 N1 C8 172.19(19) . . . . ?
C9 C8 N1 C7 136.6(2) . . . . ?
C13 C8 N1 C7 -47.2(3) . . . . ?
C17 C16 N2 C21 -4.0(4) . . . . ?
C15 C16 N2 C21 176.9(2) . . . . ?
C26 C21 N2 C16 111.3(3) . . . . ?
C22 C21 N2 C16 -70.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O3 0.82 1.84 2.661(2) 176.8 1_546
O4 H4A O1 0.82 1.85 2.668(2) 178.4 1_564

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.035

#===END

data_2
_database_code_depnum_ccdc_archive 'CCDC 709894'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25

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                   6.4397(13)
_cell_length_b                   7.3561(15)
_cell_length_c                   13.882(3)
_cell_angle_alpha                93.33(3)
_cell_angle_beta                 91.87(3)
_cell_angle_gamma                113.99(3)
_cell_volume                     598.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3787
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9719
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   
;
Higash,T(1995) Progrom for Absorption Correcttion.
Rigaku Corporation,Tokyo,Japan.
;
_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  'Omega scan'
_diffrn_measurement_method       10.0
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            5927
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2714
_reflns_number_gt                1535
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0504P)^2^+0.1753P] 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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2714
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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 0.2206(4) -0.0730(3) 0.06645(14) 0.0457(5) Uani 1 1 d . . .
C2 C 0.0048(3) -0.1261(3) 0.11313(14) 0.0437(5) Uani 1 1 d . . .
C3 C -0.1784(4) -0.3056(3) 0.08263(16) 0.0527(6) Uani 1 1 d . . .
H3 H -0.1585 -0.3904 0.0350 0.063 Uiso 1 1 calc R . .
C4 C -0.3866(4) -0.3600(3) 0.12089(17) 0.0599(6) Uani 1 1 d . . .
H4 H -0.5074 -0.4792 0.0990 0.072 Uiso 1 1 calc R . .
C5 C -0.4141(4) -0.2348(3) 0.19251(17) 0.0562(6) Uani 1 1 d . . .
H5 H -0.5553 -0.2702 0.2185 0.067 Uiso 1 1 calc R . .
C6 C -0.2374(4) -0.0595(3) 0.22611(16) 0.0538(6) Uani 1 1 d . . .
H6 H -0.2597 0.0209 0.2753 0.065 Uiso 1 1 calc R . .
C7 C -0.0235(3) 0.0003(3) 0.18729(15) 0.0455(5) Uani 1 1 d . . .
C8 C 0.1435(4) 0.3310(3) 0.28189(15) 0.0467(5) Uani 1 1 d . . .
C9 C 0.3079(4) 0.4195(3) 0.35640(16) 0.0579(6) Uani 1 1 d . . .
H9 H 0.4176 0.3706 0.3688 0.070 Uiso 1 1 calc R . .
C10 C 0.3085(5) 0.5812(4) 0.41243(16) 0.0677(7) Uani 1 1 d . . .
H10 H 0.4207 0.6405 0.4621 0.081 Uiso 1 1 calc R . .
C11 C 0.1484(4) 0.6567(3) 0.39693(17) 0.0598(6) Uani 1 1 d . . .
C12 C -0.0141(4) 0.5675(3) 0.32189(18) 0.0600(6) Uani 1 1 d . . .
H12 H -0.1244 0.6161 0.3100 0.072 Uiso 1 1 calc R . .
C13 C -0.0160(4) 0.4076(3) 0.26423(17) 0.0573(6) Uani 1 1 d . . .
H13 H -0.1253 0.3512 0.2132 0.069 Uiso 1 1 calc R . .
C14 C 0.1479(6) 0.8334(4) 0.4589(2) 0.0971(10) Uani 1 1 d . . .
H14A H 0.1260 0.9259 0.4181 0.146 Uiso 1 1 calc R . .
H14B H 0.2909 0.8984 0.4958 0.146 Uiso 1 1 calc R . .
H14C H 0.0266 0.7876 0.5020 0.146 Uiso 1 1 calc R . .
N1 N 0.1554(3) 0.1735(3) 0.22162(14) 0.0576(5) Uani 1 1 d . . .
H1 H 0.2884 0.1882 0.2049 0.069 Uiso 1 1 calc R . .
O1 O 0.3932(2) 0.0796(2) 0.08955(11) 0.0558(4) Uani 1 1 d . . .
O2 O 0.2178(3) -0.2012(2) -0.00408(11) 0.0605(5) Uani 1 1 d . . .
H2 H 0.3430 -0.1618 -0.0269 0.091 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
C1 0.0534(13) 0.0415(11) 0.0468(12) -0.0032(9) 0.0008(10) 0.0251(10)
C2 0.0524(12) 0.0386(11) 0.0419(11) 0.0024(9) 0.0038(10) 0.0206(10)
C3 0.0581(14) 0.0443(12) 0.0523(13) -0.0030(10) -0.0010(11) 0.0187(11)
C4 0.0564(14) 0.0476(13) 0.0632(15) 0.0021(11) 0.0018(12) 0.0088(11)
C5 0.0520(13) 0.0538(14) 0.0626(15) 0.0134(12) 0.0111(11) 0.0196(11)
C6 0.0606(14) 0.0457(12) 0.0542(13) 0.0033(10) 0.0148(11) 0.0201(11)
C7 0.0504(12) 0.0400(11) 0.0467(12) 0.0024(9) 0.0037(10) 0.0191(10)
C8 0.0517(12) 0.0386(11) 0.0472(12) -0.0010(9) 0.0103(10) 0.0157(10)
C9 0.0651(15) 0.0543(13) 0.0576(14) -0.0010(11) 0.0016(12) 0.0287(12)
C10 0.0867(18) 0.0588(15) 0.0472(14) -0.0096(11) -0.0053(13) 0.0216(14)
C11 0.0770(17) 0.0466(13) 0.0568(14) -0.0012(11) 0.0196(13) 0.0259(13)
C12 0.0590(14) 0.0491(13) 0.0765(17) -0.0004(12) 0.0084(13) 0.0273(11)
C13 0.0609(14) 0.0496(13) 0.0586(14) -0.0060(11) -0.0012(11) 0.0215(11)
C14 0.129(3) 0.0623(17) 0.094(2) -0.0214(15) 0.028(2) 0.0347(18)
N1 0.0515(11) 0.0475(10) 0.0678(13) -0.0149(9) 0.0123(9) 0.0160(9)
O1 0.0522(9) 0.0496(9) 0.0610(10) -0.0129(7) 0.0077(7) 0.0179(8)
O2 0.0594(10) 0.0552(9) 0.0615(10) -0.0167(8) 0.0095(8) 0.0203(8)

_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 O1 1.232(2) . ?
C1 O2 1.314(2) . ?
C1 C2 1.466(3) . ?
C2 C3 1.397(3) . ?
C2 C7 1.413(3) . ?
C3 C4 1.369(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.371(3) . ?
C6 C7 1.402(3) . ?
C7 N1 1.370(3) . ?
C8 C13 1.379(3) . ?
C8 C9 1.380(3) . ?
C8 N1 1.419(3) . ?
C9 C10 1.381(3) . ?
C10 C11 1.372(3) . ?
C11 C12 1.379(3) . ?
C11 C14 1.517(3) . ?
C12 C13 1.380(3) . ?

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
O1 C1 O2 121.28(19) . . ?
O1 C1 C2 123.94(18) . . ?
O2 C1 C2 114.77(18) . . ?
C3 C2 C7 119.15(19) . . ?
C3 C2 C1 119.04(18) . . ?
C7 C2 C1 121.81(18) . . ?
C4 C3 C2 121.8(2) . . ?
C3 C4 C5 118.8(2) . . ?
C6 C5 C4 121.3(2) . . ?
C5 C6 C7 120.8(2) . . ?
N1 C7 C6 121.27(19) . . ?
N1 C7 C2 120.64(18) . . ?
C6 C7 C2 118.07(19) . . ?
C13 C8 C9 119.1(2) . . ?
C13 C8 N1 122.3(2) . . ?
C9 C8 N1 118.5(2) . . ?
C8 C9 C10 119.6(2) . . ?
C11 C10 C9 121.9(2) . . ?
C10 C11 C12 117.8(2) . . ?
C10 C11 C14 122.0(3) . . ?
C12 C11 C14 120.2(3) . . ?
C11 C12 C13 121.2(2) . . ?
C8 C13 C12 120.3(2) . . ?
C7 N1 C8 126.63(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.82 1.82 2.641(2) 174.4 2_655

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.039

data_3
_database_code_depnum_ccdc_archive 'CCDC 709895'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H19 N O2'
_chemical_formula_weight         269.33

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                   6.7328(13)
_cell_length_b                   7.8277(16)
_cell_length_c                   15.269(3)
_cell_angle_alpha                93.68(3)
_cell_angle_beta                 90.46(3)
_cell_angle_gamma                112.33(3)
_cell_volume                     742.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3781
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      27.76

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9786
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   
;
Higash,T(1995) Progrom for Absorption Correcttion.
Rigaku Corporation,Tokyo,Japan.
;
_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  'Omega scan'
_diffrn_measurement_method       10.0
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            7326
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_sigmaI/netI    0.1202
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3367
_reflns_number_gt                1302
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.1246P)^2^+0.9272P] 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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3367
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2380
_refine_ls_R_factor_gt           0.1068
_refine_ls_wR_factor_ref         0.3101
_refine_ls_wR_factor_gt          0.2324
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_restrained_S_all      0.930
_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 0.2131(7) -0.0718(6) 0.0560(3) 0.0498(12) Uani 1 1 d . . .
C2 C 0.3797(7) -0.1244(6) 0.0931(3) 0.0487(11) Uani 1 1 d . . .
C3 C 0.3769(8) -0.3015(6) 0.0720(3) 0.0565(13) Uani 1 1 d . . .
H3 H 0.2690 -0.3833 0.0341 0.068 Uiso 1 1 calc R . .
C4 C 0.5284(9) -0.3577(7) 0.1058(4) 0.0644(14) Uani 1 1 d . . .
H4 H 0.5238 -0.4762 0.0910 0.077 Uiso 1 1 calc R . .
C5 C 0.6879(9) -0.2372(7) 0.1618(4) 0.0645(14) Uani 1 1 d . . .
H5 H 0.7913 -0.2751 0.1851 0.077 Uiso 1 1 calc R . .
C6 C 0.6968(8) -0.0622(7) 0.1839(3) 0.0637(14) Uani 1 1 d . . .
H6 H 0.8062 0.0164 0.2221 0.076 Uiso 1 1 calc R . .
C7 C 0.5459(8) 0.0012(6) 0.1505(3) 0.0512(12) Uani 1 1 d . . .
C8 C 0.7034(8) 0.3125(6) 0.2311(3) 0.0543(13) Uani 1 1 d . . .
C9 C 0.9216(9) 0.3791(7) 0.2153(4) 0.0710(16) Uani 1 1 d . . .
H9 H 0.9719 0.3287 0.1678 0.085 Uiso 1 1 calc R . .
C10 C 1.0643(8) 0.5209(7) 0.2706(4) 0.0638(14) Uani 1 1 d . . .
H10 H 1.2100 0.5635 0.2594 0.077 Uiso 1 1 calc R . .
C11 C 0.9981(7) 0.6006(6) 0.3411(3) 0.0484(12) Uani 1 1 d . . .
C12 C 0.7794(8) 0.5332(7) 0.3545(3) 0.0567(13) Uani 1 1 d . . .
H12 H 0.7280 0.5844 0.4013 0.068 Uiso 1 1 calc R . .
C13 C 0.6362(8) 0.3922(6) 0.3003(3) 0.0562(13) Uani 1 1 d . . .
H13 H 0.4903 0.3506 0.3113 0.067 Uiso 1 1 calc R . .
C14 C 1.1559(8) 0.7620(7) 0.3989(3) 0.0577(13) Uani 1 1 d . . .
C15 C 1.0725(10) 0.7815(7) 0.4899(4) 0.0748(17) Uani 1 1 d . . .
H15A H 0.9451 0.8079 0.4847 0.112 Uiso 1 1 calc R . .
H15B H 1.1804 0.8807 0.5245 0.112 Uiso 1 1 calc R . .
H15C H 1.0396 0.6680 0.5180 0.112 Uiso 1 1 calc R . .
C16 C 1.3689(10) 0.7353(11) 0.4116(5) 0.110(3) Uani 1 1 d . . .
H16A H 1.3398 0.6123 0.4286 0.165 Uiso 1 1 calc R . .
H16B H 1.4562 0.8238 0.4567 0.165 Uiso 1 1 calc R . .
H16C H 1.4436 0.7530 0.3576 0.165 Uiso 1 1 calc R . .
C17 C 1.1958(12) 0.9404(8) 0.3539(4) 0.103(2) Uani 1 1 d . . .
H17A H 1.2420 0.9282 0.2953 0.154 Uiso 1 1 calc R . .
H17B H 1.3051 1.0421 0.3865 0.154 Uiso 1 1 calc R . .
H17C H 1.0654 0.9630 0.3516 0.154 Uiso 1 1 calc R . .
N1 N 0.5516(7) 0.1740(5) 0.1731(3) 0.0635(12) Uani 1 1 d . . .
H1 H 0.4526 0.2026 0.1499 0.076 Uiso 1 1 calc R . .
O1 O 0.0724(6) -0.2009(5) 0.0027(2) 0.0660(11) Uani 1 1 d . . .
H1A H -0.0170 -0.1627 -0.0154 0.099 Uiso 1 1 calc R . .
O2 O 0.1986(5) 0.0788(4) 0.0726(2) 0.0630(10) 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 0.050(3) 0.042(3) 0.053(3) -0.002(2) -0.004(2) 0.014(2)
C2 0.054(3) 0.038(2) 0.052(3) 0.004(2) 0.002(2) 0.015(2)
C3 0.059(3) 0.043(3) 0.062(3) 0.000(2) -0.005(3) 0.014(2)
C4 0.080(4) 0.050(3) 0.068(3) 0.003(3) -0.002(3) 0.030(3)
C5 0.077(4) 0.060(3) 0.067(3) 0.014(3) -0.003(3) 0.037(3)
C6 0.062(3) 0.053(3) 0.071(4) 0.006(3) -0.018(3) 0.016(3)
C7 0.056(3) 0.041(3) 0.055(3) 0.003(2) -0.004(2) 0.017(2)
C8 0.057(3) 0.044(3) 0.059(3) -0.001(2) -0.011(3) 0.016(2)
C9 0.068(4) 0.065(4) 0.069(4) -0.018(3) -0.002(3) 0.017(3)
C10 0.050(3) 0.058(3) 0.073(4) -0.011(3) 0.004(3) 0.011(3)
C11 0.050(3) 0.037(2) 0.051(3) 0.001(2) -0.006(2) 0.010(2)
C12 0.059(3) 0.049(3) 0.058(3) -0.006(2) -0.002(3) 0.019(3)
C13 0.045(3) 0.044(3) 0.076(4) 0.002(3) -0.007(3) 0.014(2)
C14 0.050(3) 0.044(3) 0.069(3) -0.006(2) -0.009(3) 0.008(2)
C15 0.087(4) 0.054(3) 0.069(4) -0.009(3) -0.013(3) 0.014(3)
C16 0.064(4) 0.117(6) 0.133(6) -0.060(5) -0.033(4) 0.028(4)
C17 0.132(6) 0.050(4) 0.090(5) 0.004(3) 0.008(4) -0.004(4)
N1 0.068(3) 0.043(2) 0.079(3) -0.011(2) -0.030(2) 0.023(2)
O1 0.061(2) 0.052(2) 0.081(3) -0.0189(19) -0.0265(19) 0.0214(18)
O2 0.065(2) 0.048(2) 0.076(2) -0.0123(17) -0.0192(18) 0.0241(18)

_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 O2 1.230(5) . ?
C1 O1 1.318(5) . ?
C1 C2 1.455(6) . ?
C2 C3 1.397(6) . ?
C2 C7 1.423(6) . ?
C3 C4 1.364(7) . ?
C4 C5 1.374(7) . ?
C5 C6 1.368(7) . ?
C6 C7 1.394(7) . ?
C7 N1 1.361(6) . ?
C8 C13 1.360(6) . ?
C8 C9 1.389(7) . ?
C8 N1 1.423(6) . ?
C9 C10 1.387(7) . ?
C10 C11 1.371(6) . ?
C11 C12 1.384(6) . ?
C11 C14 1.525(6) . ?
C12 C13 1.376(6) . ?
C14 C15 1.523(7) . ?
C14 C17 1.529(8) . ?
C14 C16 1.538(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 121.2(4) . . ?
O2 C1 C2 124.2(4) . . ?
O1 C1 C2 114.6(4) . . ?
C3 C2 C7 119.2(4) . . ?
C3 C2 C1 119.5(4) . . ?
C7 C2 C1 121.4(4) . . ?
C4 C3 C2 121.6(5) . . ?
C3 C4 C5 119.3(5) . . ?
C6 C5 C4 120.9(5) . . ?
C5 C6 C7 121.7(5) . . ?
N1 C7 C6 122.1(4) . . ?
N1 C7 C2 120.5(4) . . ?
C6 C7 C2 117.3(4) . . ?
C13 C8 C9 118.2(4) . . ?
C13 C8 N1 120.4(5) . . ?
C9 C8 N1 121.2(5) . . ?
C10 C9 C8 119.8(5) . . ?
C11 C10 C9 122.4(5) . . ?
C10 C11 C12 116.5(4) . . ?
C10 C11 C14 121.7(4) . . ?
C12 C11 C14 121.7(4) . . ?
C13 C12 C11 121.7(5) . . ?
C8 C13 C12 121.4(5) . . ?
C15 C14 C11 112.8(4) . . ?
C15 C14 C17 108.4(5) . . ?
C11 C14 C17 108.3(4) . . ?
C15 C14 C16 107.2(5) . . ?
C11 C14 C16 110.2(4) . . ?
C17 C14 C16 109.9(6) . . ?
C7 N1 C8 127.0(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O2 0.82 1.83 2.645(5) 170.9 2
C9 H9 O1 0.93 2.70 3.532(6) 149.2 2_655

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.045

_publ_section_comment            
;
the ratio of observed/unique reflections
(_reflns_number_gt/ _reflns_number_total)
is rather low for this dataset.This probably means that the sample diffracted
only weakly at higher angles and could be the cause of the slightly high R1
and wR2 factors as well
;


#===END

data_4
_database_code_depnum_ccdc_archive 'CCDC 709896'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28

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 0.0016 '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                   4.0126(8)
_cell_length_b                   13.932(3)
_cell_length_c                   22.026(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.45(3)
_cell_angle_gamma                90.00
_cell_volume                     1229.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7104
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9830
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   
;
Higash,T(1995) Progrom for Absorption Correcttion.
Rigaku Corporation,Tokyo,Japan.
;
_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  'Omega scan'
_diffrn_measurement_method       10.0
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            11680
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2776
_reflns_number_gt                1802
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.1058P)^2^+0.0851P] 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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2776
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1793
_refine_ls_wR_factor_gt          0.1580
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.063
_refine_ls_shift/su_mean         0.002

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 1.2551(5) 0.87972(15) 0.98579(8) 0.0424(5) Uani 1 1 d . . .
C2 C 1.0823(5) 0.78859(14) 0.97579(8) 0.0378(5) Uani 1 1 d . . .
C3 C 1.0543(5) 0.72545(15) 1.02446(9) 0.0446(5) Uani 1 1 d . . .
H3 H 1.1455 0.7430 1.0627 0.054 Uiso 1 1 calc R . .
C4 C 0.8976(6) 0.63880(16) 1.01787(9) 0.0513(6) Uani 1 1 d . . .
H4 H 0.8863 0.5974 1.0508 0.062 Uiso 1 1 calc R . .
C5 C 0.7559(6) 0.61387(16) 0.96127(9) 0.0488(5) Uani 1 1 d . . .
H5 H 0.6442 0.5556 0.9565 0.059 Uiso 1 1 calc R . .
C6 C 0.7769(5) 0.67335(15) 0.91213(9) 0.0437(5) Uani 1 1 d . . .
H6 H 0.6788 0.6548 0.8746 0.052 Uiso 1 1 calc R . .
C7 C 0.9430(5) 0.76148(14) 0.91722(8) 0.0377(5) Uani 1 1 d . . .
C8 C 0.8595(5) 0.80432(15) 0.80710(8) 0.0399(5) Uani 1 1 d . . .
C9 C 0.9390(5) 0.72043(14) 0.77743(9) 0.0415(5) Uani 1 1 d . . .
H9 H 1.0513 0.6715 0.7988 0.050 Uiso 1 1 calc R . .
C10 C 0.8514(5) 0.70925(15) 0.71585(8) 0.0393(5) Uani 1 1 d . . .
C11 C 0.6864(5) 0.78311(15) 0.68476(8) 0.0419(5) Uani 1 1 d . . .
H11 H 0.6269 0.7757 0.6436 0.050 Uiso 1 1 calc R . .
C12 C 0.6075(5) 0.86781(15) 0.71355(9) 0.0416(5) Uani 1 1 d . . .
C13 C 0.6910(5) 0.87691(14) 0.77518(8) 0.0420(5) Uani 1 1 d . . .
H13 H 0.6332 0.9325 0.7954 0.050 Uiso 1 1 calc R . .
C14 C 0.9424(6) 0.61883(17) 0.68337(10) 0.0567(6) Uani 1 1 d . . .
H14A H 1.1336 0.5899 0.7043 0.085 Uiso 1 1 calc R . .
H14B H 0.9938 0.6341 0.6425 0.085 Uiso 1 1 calc R . .
H14C H 0.7580 0.5749 0.6826 0.085 Uiso 1 1 calc R . .
C15 C 0.4386(6) 0.94907(18) 0.67843(11) 0.0596(6) Uani 1 1 d . . .
H15A H 0.2938 0.9828 0.7042 0.089 Uiso 1 1 calc R . .
H15B H 0.3100 0.9237 0.6439 0.089 Uiso 1 1 calc R . .
H15C H 0.6046 0.9924 0.6648 0.089 Uiso 1 1 calc R . .
N1 N 0.9613(5) 0.82186(13) 0.86873(7) 0.0507(5) Uani 1 1 d . . .
H1 H 1.0453 0.8776 0.8766 0.061 Uiso 1 1 calc R . .
O1 O 1.2851(4) 0.94156(11) 0.94661(6) 0.0581(5) Uani 1 1 d . . .
O2 O 1.3858(4) 0.89290(11) 1.04179(6) 0.0546(5) Uani 1 1 d . . .
H2 H 1.4821 0.9448 1.0439 0.082 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
C1 0.0528(12) 0.0408(12) 0.0327(10) -0.0063(8) -0.0061(9) 0.0019(9)
C2 0.0420(10) 0.0370(11) 0.0339(10) -0.0057(7) -0.0018(8) 0.0010(8)
C3 0.0516(12) 0.0473(13) 0.0343(10) -0.0010(8) -0.0031(9) 0.0013(10)
C4 0.0658(14) 0.0474(13) 0.0409(11) 0.0067(9) 0.0037(10) -0.0022(11)
C5 0.0587(13) 0.0407(12) 0.0473(12) -0.0022(9) 0.0053(10) -0.0110(10)
C6 0.0519(12) 0.0410(12) 0.0376(10) -0.0047(8) -0.0021(9) -0.0070(9)
C7 0.0425(10) 0.0377(11) 0.0325(9) -0.0042(8) 0.0001(7) -0.0005(8)
C8 0.0472(11) 0.0393(11) 0.0325(10) -0.0011(7) -0.0029(8) -0.0089(9)
C9 0.0446(11) 0.0380(11) 0.0411(11) 0.0032(8) -0.0040(8) -0.0016(9)
C10 0.0424(10) 0.0402(11) 0.0354(10) -0.0036(8) 0.0026(8) -0.0038(8)
C11 0.0452(11) 0.0481(12) 0.0318(9) 0.0016(8) -0.0031(8) -0.0063(9)
C12 0.0429(11) 0.0426(12) 0.0388(10) 0.0085(8) -0.0021(8) -0.0038(9)
C13 0.0514(12) 0.0326(10) 0.0418(11) -0.0016(8) 0.0010(9) -0.0038(9)
C14 0.0731(16) 0.0485(14) 0.0490(12) -0.0080(10) 0.0086(11) 0.0002(11)
C15 0.0640(14) 0.0587(15) 0.0553(13) 0.0161(11) -0.0021(11) 0.0095(12)
N1 0.0783(13) 0.0388(10) 0.0332(9) -0.0009(7) -0.0116(8) -0.0166(9)
O1 0.0895(12) 0.0431(9) 0.0394(8) -0.0006(6) -0.0155(8) -0.0170(8)
O2 0.0753(11) 0.0510(10) 0.0359(8) -0.0052(6) -0.0105(7) -0.0142(8)

_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 O1 1.231(2) . ?
C1 O2 1.324(2) . ?
C1 C2 1.457(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.426(3) . ?
C3 C4 1.365(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.370(3) . ?
C6 C7 1.398(3) . ?
C7 N1 1.365(2) . ?
C8 C13 1.385(3) . ?
C8 C9 1.385(3) . ?
C8 N1 1.415(2) . ?
C9 C10 1.389(3) . ?
C10 C11 1.383(3) . ?
C10 C14 1.505(3) . ?
C11 C12 1.385(3) . ?
C12 C13 1.384(3) . ?
C12 C15 1.509(3) . ?

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
O1 C1 O2 120.42(18) . . ?
O1 C1 C2 124.74(17) . . ?
O2 C1 C2 114.83(17) . . ?
C3 C2 C7 118.83(18) . . ?
C3 C2 C1 119.51(17) . . ?
C7 C2 C1 121.66(18) . . ?
C4 C3 C2 122.24(19) . . ?
C3 C4 C5 118.7(2) . . ?
C6 C5 C4 121.3(2) . . ?
C5 C6 C7 121.29(18) . . ?
N1 C7 C6 121.74(17) . . ?
N1 C7 C2 120.54(18) . . ?
C6 C7 C2 117.67(18) . . ?
C13 C8 C9 119.73(17) . . ?
C13 C8 N1 117.70(18) . . ?
C9 C8 N1 122.46(18) . . ?
C8 C9 C10 120.21(18) . . ?
C11 C10 C9 119.04(18) . . ?
C11 C10 C14 120.69(18) . . ?
C9 C10 C14 120.25(19) . . ?
C10 C11 C12 121.55(17) . . ?
C13 C12 C11 118.57(18) . . ?
C13 C12 C15 120.6(2) . . ?
C11 C12 C15 120.84(19) . . ?
C12 C13 C8 120.87(19) . . ?
C7 N1 C8 128.19(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.82 1.84 2.662(2) 176.0 3_877

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.041