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


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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  fide research purposes only. It may contain copyright material 
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data_shelx
_database_code_depnum_ccdc_archive 'CCDC 862108'
#TrackingRef '9008_web_deposit_cif_file_0_LihuaYang_1326245625.shelx.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 N O3'
_chemical_formula_weight         305.32

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   5.551(3)
_cell_length_b                   11.084(6)
_cell_length_c                   24.666(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1517.5(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    5029
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      28.0

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          12.00
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.4083
_exptl_absorpt_correction_T_max  0.9838
_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 Saturn724 CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean 14.22
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15639
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         27.95
_reflns_number_total             3619
_reflns_number_gt                3010
_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^)+(0.0378P)^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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(12)
_refine_ls_number_reflns         3619
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.0927
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.2104(2) 0.57194(10) 0.13575(4) 0.0289(3) Uani 1 1 d . . .
O2 O 0.0311(2) 0.47073(14) 0.26414(5) 0.0477(4) Uani 1 1 d . . .
O3 O 0.4226(2) 0.74061(12) 0.21538(5) 0.0378(3) Uani 1 1 d . . .
N1 N 0.2959(3) 0.86382(13) 0.14561(6) 0.0298(3) Uani 1 1 d . . .
C1 C 0.1098(3) 0.86040(16) 0.10690(7) 0.0288(4) Uani 1 1 d . . .
C2 C 0.0514(4) 0.94677(17) 0.06897(7) 0.0372(5) Uani 1 1 d . . .
H2 H 0.1423 1.0190 0.0657 0.045 Uiso 1 1 calc R . .
C3 C -0.1459(4) 0.9242(2) 0.03558(7) 0.0418(5) Uani 1 1 d . . .
H3 H -0.1911 0.9825 0.0093 0.050 Uiso 1 1 calc R . .
C4 C -0.2769(4) 0.81887(19) 0.03988(7) 0.0401(5) Uani 1 1 d . . .
H4 H -0.4103 0.8055 0.0165 0.048 Uiso 1 1 calc R . .
C5 C -0.2148(3) 0.73186(17) 0.07836(7) 0.0326(4) Uani 1 1 d . . .
H5 H -0.3057 0.6596 0.0817 0.039 Uiso 1 1 calc R . .
C6 C -0.0194(3) 0.75282(15) 0.11125(6) 0.0269(4) Uani 1 1 d . . .
C7 C 0.0887(3) 0.68044(15) 0.15647(7) 0.0266(4) Uani 1 1 d . . .
C8 C 0.2897(3) 0.76403(17) 0.17719(7) 0.0297(4) Uani 1 1 d . . .
C9 C 0.4545(3) 0.96625(17) 0.15543(8) 0.0398(5) Uani 1 1 d . . .
H9A H 0.3622 1.0320 0.1720 0.060 Uiso 1 1 calc R . .
H9B H 0.5232 0.9937 0.1210 0.060 Uiso 1 1 calc R . .
H9C H 0.5847 0.9419 0.1799 0.060 Uiso 1 1 calc R . .
C10 C -0.0704(3) 0.63557(17) 0.20236(7) 0.0340(4) Uani 1 1 d . . .
H10A H -0.0826 0.6962 0.2317 0.041 Uiso 1 1 calc R . .
H10B H -0.2341 0.6156 0.1892 0.041 Uiso 1 1 calc R . .
C11 C 0.0616(3) 0.52375(18) 0.22134(7) 0.0345(4) Uani 1 1 d . . .
C12 C 0.2312(3) 0.49025(16) 0.17801(7) 0.0286(4) Uani 1 1 d . . .
C13 C 0.3812(3) 0.39627(16) 0.17941(7) 0.0308(4) Uani 1 1 d . . .
H13 H 0.3657 0.3460 0.2104 0.037 Uiso 1 1 calc R . .
C14 C 0.5657(3) 0.35852(16) 0.14072(7) 0.0298(4) Uani 1 1 d . . .
C15 C 0.5915(4) 0.40954(17) 0.08944(7) 0.0358(4) Uani 1 1 d . . .
H15 H 0.4804 0.4690 0.0774 0.043 Uiso 1 1 calc R . .
C16 C 0.7789(4) 0.37385(18) 0.05595(8) 0.0425(5) Uani 1 1 d . . .
H16 H 0.7975 0.4104 0.0214 0.051 Uiso 1 1 calc R . .
C17 C 0.9386(4) 0.28574(19) 0.07239(8) 0.0460(5) Uani 1 1 d . . .
H17 H 1.0663 0.2615 0.0492 0.055 Uiso 1 1 calc R . .
C18 C 0.9118(4) 0.23303(19) 0.12279(8) 0.0453(5) Uani 1 1 d . . .
H18 H 1.0210 0.1722 0.1342 0.054 Uiso 1 1 calc R . .
C19 C 0.7271(3) 0.26856(17) 0.15643(8) 0.0367(5) Uani 1 1 d . . .
H19 H 0.7093 0.2313 0.1909 0.044 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 0.0310(7) 0.0266(6) 0.0292(6) 0.0014(5) 0.0015(6) 0.0059(6)
O2 0.0368(8) 0.0632(10) 0.0429(8) 0.0212(7) 0.0093(7) 0.0090(7)
O3 0.0315(7) 0.0454(8) 0.0364(7) -0.0073(6) -0.0065(6) 0.0072(7)
N1 0.0263(8) 0.0290(8) 0.0341(8) -0.0040(7) 0.0006(7) -0.0007(7)
C1 0.0286(10) 0.0303(10) 0.0273(8) -0.0038(8) 0.0031(8) 0.0056(8)
C2 0.0464(12) 0.0309(10) 0.0344(9) 0.0033(8) 0.0098(10) 0.0042(10)
C3 0.0535(14) 0.0426(12) 0.0294(9) 0.0058(9) 0.0017(9) 0.0149(11)
C4 0.0418(12) 0.0464(12) 0.0320(10) -0.0010(9) -0.0048(9) 0.0108(11)
C5 0.0319(10) 0.0332(10) 0.0327(9) -0.0028(8) -0.0015(8) 0.0041(9)
C6 0.0272(10) 0.0274(9) 0.0262(8) -0.0016(8) -0.0001(7) 0.0057(8)
C7 0.0250(9) 0.0268(9) 0.0281(8) -0.0018(7) 0.0027(8) 0.0050(8)
C8 0.0254(9) 0.0340(10) 0.0296(9) -0.0058(8) 0.0042(8) 0.0068(9)
C9 0.0336(11) 0.0374(11) 0.0484(11) -0.0090(9) 0.0066(10) -0.0059(10)
C10 0.0268(10) 0.0417(11) 0.0335(9) 0.0039(9) 0.0044(8) 0.0061(9)
C11 0.0228(9) 0.0441(11) 0.0366(10) 0.0092(9) 0.0007(9) 0.0010(9)
C12 0.0260(9) 0.0303(9) 0.0294(9) 0.0062(7) -0.0008(8) -0.0009(8)
C13 0.0296(10) 0.0289(10) 0.0337(9) 0.0060(8) -0.0004(8) -0.0005(8)
C14 0.0311(10) 0.0260(9) 0.0324(9) -0.0009(8) -0.0040(9) -0.0004(9)
C15 0.0396(11) 0.0313(10) 0.0364(10) 0.0003(8) -0.0023(9) 0.0056(10)
C16 0.0504(13) 0.0395(11) 0.0378(10) -0.0012(9) 0.0069(10) 0.0083(11)
C17 0.0450(12) 0.0489(13) 0.0441(11) -0.0128(10) 0.0041(11) 0.0140(12)
C18 0.0490(12) 0.0440(12) 0.0429(11) -0.0100(10) -0.0074(10) 0.0196(11)
C19 0.0425(11) 0.0328(10) 0.0349(9) -0.0025(8) -0.0067(9) 0.0078(10)

_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 C12 1.3857(19) . ?
O1 C7 1.471(2) . ?
O2 C11 1.220(2) . ?
O3 C8 1.224(2) . ?
N1 C8 1.353(2) . ?
N1 C1 1.407(2) . ?
N1 C9 1.457(2) . ?
C1 C2 1.377(2) . ?
C1 C6 1.396(2) . ?
C2 C3 1.393(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.499(2) . ?
C7 C10 1.520(2) . ?
C7 C8 1.537(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.514(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.472(2) . ?
C12 C13 1.334(2) . ?
C13 C14 1.461(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(2) . ?
C14 C19 1.396(2) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(3) . ?
C18 H18 0.9500 . ?
C19 H19 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
C12 O1 C7 108.12(12) . . ?
C8 N1 C1 110.46(15) . . ?
C8 N1 C9 123.84(16) . . ?
C1 N1 C9 125.26(15) . . ?
C2 C1 C6 121.69(17) . . ?
C2 C1 N1 127.94(18) . . ?
C6 C1 N1 110.37(15) . . ?
C1 C2 C3 117.48(19) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 121.43(19) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.42(18) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.65(18) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 120.31(16) . . ?
C5 C6 C7 131.66(17) . . ?
C1 C6 C7 107.97(15) . . ?
O1 C7 C6 111.28(13) . . ?
O1 C7 C10 104.96(14) . . ?
C6 C7 C10 119.78(15) . . ?
O1 C7 C8 105.97(13) . . ?
C6 C7 C8 102.44(15) . . ?
C10 C7 C8 111.78(14) . . ?
O3 C8 N1 126.92(18) . . ?
O3 C8 C7 124.41(17) . . ?
N1 C8 C7 108.65(15) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 102.54(15) . . ?
C11 C10 H10A 111.3 . . ?
C7 C10 H10A 111.3 . . ?
C11 C10 H10B 111.3 . . ?
C7 C10 H10B 111.3 . . ?
H10A C10 H10B 109.2 . . ?
O2 C11 C12 126.56(19) . . ?
O2 C11 C10 126.49(18) . . ?
C12 C11 C10 106.95(15) . . ?
C13 C12 O1 125.55(16) . . ?
C13 C12 C11 125.28(16) . . ?
O1 C12 C11 109.17(15) . . ?
C12 C13 C14 130.12(16) . . ?
C12 C13 H13 114.9 . . ?
C14 C13 H13 114.9 . . ?
C15 C14 C19 118.43(18) . . ?
C15 C14 C13 123.30(17) . . ?
C19 C14 C13 118.25(16) . . ?
C16 C15 C14 120.18(19) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.59(19) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.63(19) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 120.11(19) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 121.02(18) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 177.46(17) . . . . ?
C9 N1 C1 C2 4.8(3) . . . . ?
C8 N1 C1 C6 -2.41(19) . . . . ?
C9 N1 C1 C6 -175.04(15) . . . . ?
C6 C1 C2 C3 1.4(2) . . . . ?
N1 C1 C2 C3 -178.46(16) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 1.5(2) . . . . ?
C4 C5 C6 C7 178.40(17) . . . . ?
C2 C1 C6 C5 -1.9(2) . . . . ?
N1 C1 C6 C5 177.98(14) . . . . ?
C2 C1 C6 C7 -179.46(15) . . . . ?
N1 C1 C6 C7 0.43(18) . . . . ?
C12 O1 C7 C6 -159.54(14) . . . . ?
C12 O1 C7 C10 -28.56(17) . . . . ?
C12 O1 C7 C8 89.86(15) . . . . ?
C5 C6 C7 O1 71.4(2) . . . . ?
C1 C6 C7 O1 -111.43(15) . . . . ?
C5 C6 C7 C10 -51.4(3) . . . . ?
C1 C6 C7 C10 125.74(17) . . . . ?
C5 C6 C7 C8 -175.77(17) . . . . ?
C1 C6 C7 C8 1.41(17) . . . . ?
C1 N1 C8 O3 -178.13(16) . . . . ?
C9 N1 C8 O3 -5.4(3) . . . . ?
C1 N1 C8 C7 3.29(18) . . . . ?
C9 N1 C8 C7 176.04(14) . . . . ?
O1 C7 C8 O3 -64.8(2) . . . . ?
C6 C7 C8 O3 178.52(15) . . . . ?
C10 C7 C8 O3 49.0(2) . . . . ?
O1 C7 C8 N1 113.86(14) . . . . ?
C6 C7 C8 N1 -2.86(17) . . . . ?
C10 C7 C8 N1 -132.34(16) . . . . ?
O1 C7 C10 C11 27.01(17) . . . . ?
C6 C7 C10 C11 152.86(16) . . . . ?
C8 C7 C10 C11 -87.41(17) . . . . ?
C7 C10 C11 O2 163.89(19) . . . . ?
C7 C10 C11 C12 -16.90(19) . . . . ?
C7 O1 C12 C13 -161.97(17) . . . . ?
C7 O1 C12 C11 17.88(18) . . . . ?
O2 C11 C12 C13 -0.9(3) . . . . ?
C10 C11 C12 C13 179.90(17) . . . . ?
O2 C11 C12 O1 179.27(18) . . . . ?
C10 C11 C12 O1 0.1(2) . . . . ?
O1 C12 C13 C14 3.9(3) . . . . ?
C11 C12 C13 C14 -175.96(18) . . . . ?
C12 C13 C14 C15 -9.8(3) . . . . ?
C12 C13 C14 C19 168.85(18) . . . . ?
C19 C14 C15 C16 -2.1(3) . . . . ?
C13 C14 C15 C16 176.46(17) . . . . ?
C14 C15 C16 C17 1.4(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C14 -0.6(3) . . . . ?
C15 C14 C19 C18 1.7(3) . . . . ?
C13 C14 C19 C18 -176.95(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.95
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046