# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014



data_global
_journal_name_full               Eur.J.Org.Chem.
_journal_coden_cambridge         1291
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
'Jianyang Chen'
'Qian He'
ChunhaoYang
_publ_contact_author_name        'Chunhao Yang'
_publ_contact_author_email       chyang@mail.shcnc.ac.cn

data_H:\Report\20120100\20120100.CIF
#TrackingRef '15222_web_deposit_cif_file_0_JianyangChen_1352210867.20120100.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            CYH-3a0
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 N3 O'
_chemical_formula_weight         313.35

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   P21/n

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

_cell_length_a                   9.1284(6)
_cell_length_b                   8.5176(6)
_cell_length_c                   20.2454(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.403(5)
_cell_angle_gamma                90.00
_cell_volume                     1561.00(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6169
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      54.87

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3283
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_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            10820
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_av_sigmaI/netI    0.0768
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2726
_reflns_number_gt                1739
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.1251P)²+0.0000P] where P=(Fo²+2Fc²)/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       0.020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         2726
_refine_ls_number_parameters     218
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.2043
_refine_ls_wR_factor_gt          0.1689
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.017
_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 0.1180(2) 0.5844(3) 0.06827(11) 0.0325(6) Uani 1 1 d . . .
N1 N 0.3834(3) 0.2104(3) 0.03982(12) 0.0268(7) Uani 1 1 d . . .
N2 N 0.1710(3) 0.3747(3) 0.00589(12) 0.0276(7) Uani 1 1 d . . .
H6 H 0.0807 0.3664 -0.0122 0.033 Uiso 1 1 calc R . .
N3 N 0.4407(3) 0.3397(3) 0.07749(12) 0.0275(7) Uani 1 1 d . . .
C1 C 0.0852(4) 0.0383(4) -0.16092(16) 0.0357(9) Uani 1 1 d . . .
H1 H 0.0507 0.0531 -0.2057 0.043 Uiso 1 1 calc R . .
C2 C 0.1580(4) 0.1581(4) -0.12429(16) 0.0328(8) Uani 1 1 d . . .
H8 H 0.1718 0.2539 -0.1446 0.039 Uiso 1 1 calc R . .
C3 C 0.2109(3) 0.1370(4) -0.05749(16) 0.0282(8) Uani 1 1 d . . .
C4 C 0.2839(3) 0.2701(4) -0.01720(15) 0.0275(8) Uani 1 1 d . . .
H7 H 0.3421 0.3311 -0.0456 0.033 Uiso 1 1 calc R . .
C5 C 0.3297(3) 0.0844(4) 0.07685(15) 0.0261(8) Uani 1 1 d . . .
C6 C 0.3877(3) 0.0690(4) 0.14870(16) 0.0261(8) Uani 1 1 d . . .
C7 C 0.4979(4) -0.0407(4) 0.16773(17) 0.0338(8) Uani 1 1 d . . .
H12 H 0.5396 -0.0968 0.1354 0.041 Uiso 1 1 calc R . .
C8 C 0.5460(4) -0.0669(4) 0.23485(18) 0.0404(9) Uani 1 1 d . . .
H11 H 0.6193 -0.1409 0.2473 0.048 Uiso 1 1 calc R . .
C9 C 0.4855(4) 0.0163(4) 0.28282(17) 0.0399(9) Uani 1 1 d . . .
H2 H 0.5161 -0.0035 0.3276 0.048 Uiso 1 1 calc R . .
C10 C 0.0639(4) -0.1045(4) -0.13046(17) 0.0365(9) Uani 1 1 d . . .
H15 H 0.0150 -0.1856 -0.1550 0.044 Uiso 1 1 calc R . .
C11 C 0.1152(3) -0.1265(4) -0.06357(17) 0.0325(8) Uani 1 1 d . . .
H14 H 0.1006 -0.2224 -0.0434 0.039 Uiso 1 1 calc R . .
C12 C 0.1885(3) -0.0055(4) -0.02633(16) 0.0268(8) Uani 1 1 d . . .
C13 C 0.2413(3) -0.0230(4) 0.04460(16) 0.0289(8) Uani 1 1 d . . .
H13 H 0.2128 -0.1101 0.0675 0.035 Uiso 1 1 calc R . .
C14 C 0.2050(3) 0.4818(4) 0.05401(15) 0.0272(8) Uani 1 1 d U . .
C15 C 0.3540(3) 0.4669(4) 0.08965(16) 0.0276(8) Uani 1 1 d . . .
C16 C 0.5755(3) 0.3499(4) 0.11448(16) 0.0306(8) Uani 1 1 d . . .
H5 H 0.6526 0.2782 0.1151 0.037 Uiso 1 1 calc R . .
C17 C 0.5765(3) 0.4852(4) 0.15046(16) 0.0310(8) Uani 1 1 d . . .
H4 H 0.6554 0.5219 0.1801 0.037 Uiso 1 1 calc R . .
C18 C 0.4395(4) 0.5600(4) 0.13561(16) 0.0318(8) Uani 1 1 d . . .
H3 H 0.4113 0.6544 0.1533 0.038 Uiso 1 1 calc R . .
C19 C 0.3800(4) 0.1285(5) 0.26478(17) 0.0375(9) Uani 1 1 d . . .
H10 H 0.3413 0.1863 0.2974 0.045 Uiso 1 1 calc R . .
C20 C 0.3307(4) 0.1562(4) 0.19774(17) 0.0344(9) Uani 1 1 d . . .
H9 H 0.2597 0.2329 0.1857 0.041 Uiso 1 1 calc R . .


_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 C14 1.240(4) . ?
N1 N3 1.401(4) . ?
N1 C5 1.432(4) . ?
N1 C4 1.465(4) . ?
N2 C14 1.341(4) . ?
N2 C4 1.482(4) . ?
N2 H6 0.8600 . ?
N3 C16 1.358(4) . ?
N3 C15 1.382(4) . ?
C1 C2 1.381(5) . ?
C1 C10 1.388(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.388(4) . ?
C2 H8 0.9300 . ?
C3 C12 1.395(5) . ?
C3 C4 1.502(5) . ?
C4 H7 0.9800 . ?
C5 C13 1.334(5) . ?
C5 C6 1.488(4) . ?
C6 C7 1.390(5) . ?
C6 C20 1.393(5) . ?
C7 C8 1.391(5) . ?
C7 H12 0.9300 . ?
C8 C9 1.374(5) . ?
C8 H11 0.9300 . ?
C9 C19 1.372(5) . ?
C9 H2 0.9300 . ?
C10 C11 1.388(5) . ?
C10 H15 0.9300 . ?
C11 C12 1.396(5) . ?
C11 H14 0.9300 . ?
C12 C13 1.462(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.461(4) . ?
C15 C18 1.384(4) . ?
C16 C17 1.363(5) . ?
C16 H5 0.9300 . ?
C17 C18 1.401(5) . ?
C17 H4 0.9300 . ?
C18 H3 0.9300 . ?
C19 C20 1.394(5) . ?
C19 H10 0.9300 . ?
C20 H9 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
N3 N1 C5 115.7(2) . . ?
N3 N1 C4 107.8(2) . . ?
C5 N1 C4 117.0(2) . . ?
C14 N2 C4 122.1(2) . . ?
C14 N2 H6 118.9 . . ?
C4 N2 H6 118.9 . . ?
C16 N3 C15 110.5(3) . . ?
C16 N3 N1 126.8(3) . . ?
C15 N3 N1 122.0(2) . . ?
C2 C1 C10 119.6(3) . . ?
C2 C1 H1 120.2 . . ?
C10 C1 H1 120.2 . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 H8 119.6 . . ?
C3 C2 H8 119.6 . . ?
C2 C3 C12 120.0(3) . . ?
C2 C3 C4 120.4(3) . . ?
C12 C3 C4 119.5(3) . . ?
N1 C4 N2 110.2(2) . . ?
N1 C4 C3 110.6(3) . . ?
N2 C4 C3 110.3(2) . . ?
N1 C4 H7 108.5 . . ?
N2 C4 H7 108.5 . . ?
C3 C4 H7 108.5 . . ?
C13 C5 N1 119.0(3) . . ?
C13 C5 C6 122.3(3) . . ?
N1 C5 C6 118.4(3) . . ?
C7 C6 C20 119.0(3) . . ?
C7 C6 C5 118.9(3) . . ?
C20 C6 C5 122.1(3) . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H12 119.9 . . ?
C8 C7 H12 119.9 . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H11 119.9 . . ?
C7 C8 H11 119.9 . . ?
C19 C9 C8 120.2(3) . . ?
C19 C9 H2 119.9 . . ?
C8 C9 H2 119.9 . . ?
C11 C10 C1 120.2(3) . . ?
C11 C10 H15 119.9 . . ?
C1 C10 H15 119.9 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H14 119.8 . . ?
C12 C11 H14 119.8 . . ?
C3 C12 C11 119.1(3) . . ?
C3 C12 C13 118.9(3) . . ?
C11 C12 C13 122.0(3) . . ?
C5 C13 C12 120.9(3) . . ?
C5 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
O1 C14 N2 123.6(3) . . ?
O1 C14 C15 122.0(3) . . ?
N2 C14 C15 114.4(3) . . ?
N3 C15 C18 106.4(3) . . ?
N3 C15 C14 119.9(3) . . ?
C18 C15 C14 133.7(3) . . ?
N3 C16 C17 107.0(3) . . ?
N3 C16 H5 126.5 . . ?
C17 C16 H5 126.5 . . ?
C16 C17 C18 109.0(3) . . ?
C16 C17 H4 125.5 . . ?
C18 C17 H4 125.5 . . ?
C15 C18 C17 107.1(3) . . ?
C15 C18 H3 126.4 . . ?
C17 C18 H3 126.4 . . ?
C9 C19 C20 120.3(3) . . ?
C9 C19 H10 119.8 . . ?
C20 C19 H10 119.8 . . ?
C6 C20 C19 120.0(3) . . ?
C6 C20 H9 120.0 . . ?
C19 C20 H9 120.0 . . ?

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
C5 N1 N3 C16 77.8(4) . . . . ?
C4 N1 N3 C16 -149.1(3) . . . . ?
C5 N1 N3 C15 -91.7(3) . . . . ?
C4 N1 N3 C15 41.4(4) . . . . ?
C10 C1 C2 C3 0.4(5) . . . . ?
C1 C2 C3 C12 -1.1(5) . . . . ?
C1 C2 C3 C4 -177.2(3) . . . . ?
N3 N1 C4 N2 -54.1(3) . . . . ?
C5 N1 C4 N2 78.3(3) . . . . ?
N3 N1 C4 C3 -176.4(2) . . . . ?
C5 N1 C4 C3 -44.0(4) . . . . ?
C14 N2 C4 N1 42.9(4) . . . . ?
C14 N2 C4 C3 165.3(3) . . . . ?
C2 C3 C4 N1 -155.9(3) . . . . ?
C12 C3 C4 N1 27.9(4) . . . . ?
C2 C3 C4 N2 81.9(4) . . . . ?
C12 C3 C4 N2 -94.3(3) . . . . ?
N3 N1 C5 C13 163.3(3) . . . . ?
C4 N1 C5 C13 34.5(4) . . . . ?
N3 N1 C5 C6 -23.1(4) . . . . ?
C4 N1 C5 C6 -151.9(3) . . . . ?
C13 C5 C6 C7 73.3(4) . . . . ?
N1 C5 C6 C7 -100.1(4) . . . . ?
C13 C5 C6 C20 -103.9(4) . . . . ?
N1 C5 C6 C20 82.7(4) . . . . ?
C20 C6 C7 C8 2.5(5) . . . . ?
C5 C6 C7 C8 -174.8(3) . . . . ?
C6 C7 C8 C9 -0.4(5) . . . . ?
C7 C8 C9 C19 -1.7(5) . . . . ?
C2 C1 C10 C11 0.1(5) . . . . ?
C1 C10 C11 C12 0.1(5) . . . . ?
C2 C3 C12 C11 1.2(5) . . . . ?
C4 C3 C12 C11 177.4(3) . . . . ?
C2 C3 C12 C13 -178.1(3) . . . . ?
C4 C3 C12 C13 -1.9(4) . . . . ?
C10 C11 C12 C3 -0.7(5) . . . . ?
C10 C11 C12 C13 178.6(3) . . . . ?
N1 C5 C13 C12 -5.5(5) . . . . ?
C6 C5 C13 C12 -178.9(3) . . . . ?
C3 C12 C13 C5 -10.7(5) . . . . ?
C11 C12 C13 C5 169.9(3) . . . . ?
C4 N2 C14 O1 170.1(3) . . . . ?
C4 N2 C14 C15 -10.8(4) . . . . ?
C16 N3 C15 C18 0.5(4) . . . . ?
N1 N3 C15 C18 171.5(3) . . . . ?
C16 N3 C15 C14 178.7(3) . . . . ?
N1 N3 C15 C14 -10.3(4) . . . . ?
O1 C14 C15 N3 172.2(3) . . . . ?
N2 C14 C15 N3 -6.9(4) . . . . ?
O1 C14 C15 C18 -10.2(6) . . . . ?
N2 C14 C15 C18 170.7(4) . . . . ?
C15 N3 C16 C17 -0.4(4) . . . . ?
N1 N3 C16 C17 -170.9(3) . . . . ?
N3 C16 C17 C18 0.2(4) . . . . ?
N3 C15 C18 C17 -0.4(4) . . . . ?
C14 C15 C18 C17 -178.2(3) . . . . ?
C16 C17 C18 C15 0.2(4) . . . . ?
C8 C9 C19 C20 1.7(5) . . . . ?
C7 C6 C20 C19 -2.5(5) . . . . ?
C5 C6 C20 C19 174.7(3) . . . . ?
C9 C19 C20 C6 0.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.085


_database_code_depnum_ccdc_archive 'CCDC 909484'
