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

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Zhiyong Wang'
_publ_contact_author_email       ZWANG3@USTC.EDU.CN

_publ_section_title              
;
A novel and efficient methodology for the construction of
quonazolines based on supported copper oxide nanoparticles
;
_publ_author_name                'Zhiyong Wang'

# Attachment 'cif.cif'

data_091207
_database_code_depnum_ccdc_archive 'CCDC 757569'
#TrackingRef 'cif.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 N2'
_chemical_formula_weight         282.33

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'

_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                   10.633
_cell_length_b                   6.965
_cell_length_c                   19.786
_cell_angle_alpha                90.00
_cell_angle_beta                 99.74
_cell_angle_gamma                90.00
_cell_volume                     1444.2
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5161
_cell_measurement_theta_min      3.0784
_cell_measurement_theta_max      36.2331

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.52
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9553
_exptl_absorpt_correction_T_max  0.9611
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12899
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2945
_reflns_number_gt                1781
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0450P)^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_number_reflns         2945
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
N2 N 0.22421(9) 0.19192(13) 0.17267(5) 0.0423(2) Uani 1 1 d . . .
C2 C 0.28615(11) 0.19348(15) 0.29522(6) 0.0391(3) Uani 1 1 d . . .
N1 N 0.44544(8) 0.19863(13) 0.22151(5) 0.0423(2) Uani 1 1 d . . .
C3 C 0.25658(11) 0.18933(15) 0.10895(6) 0.0410(3) Uani 1 1 d . . .
C4 C 0.31811(11) 0.19512(15) 0.22497(6) 0.0386(3) Uani 1 1 d . . .
C5 C 0.38519(11) 0.19526(15) 0.09935(6) 0.0400(3) Uani 1 1 d . . .
C6 C 0.47813(10) 0.20193(15) 0.16017(6) 0.0397(3) Uani 1 1 d . . .
C7 C 0.15984(11) 0.20707(17) 0.30453(6) 0.0494(3) Uani 1 1 d . . .
H7 H 0.0953 0.2181 0.2666 0.059 Uiso 1 1 calc R . .
C8 C 0.41211(12) 0.18432(17) 0.03195(6) 0.0507(3) Uani 1 1 d . . .
H8 H 0.4963 0.1876 0.0248 0.061 Uiso 1 1 calc R . .
C9 C 0.61739(11) 0.20590(17) 0.15861(6) 0.0437(3) Uani 1 1 d . . .
C10 C 0.12959(13) 0.20432(18) 0.36945(7) 0.0569(4) Uani 1 1 d . . .
H10 H 0.0448 0.2144 0.3751 0.068 Uiso 1 1 calc R . .
C11 C 0.15911(12) 0.17564(16) 0.05131(6) 0.0513(3) Uani 1 1 d . . .
H11 H 0.0742 0.1737 0.0572 0.062 Uiso 1 1 calc R . .
C12 C 0.22295(14) 0.18687(17) 0.42565(7) 0.0581(4) Uani 1 1 d . . .
H12 H 0.2019 0.1845 0.4694 0.070 Uiso 1 1 calc R . .
C13 C 0.18824(13) 0.16523(17) -0.01267(7) 0.0565(4) Uani 1 1 d . . .
H13 H 0.1231 0.1554 -0.0503 0.068 Uiso 1 1 calc R . .
C14 C 0.37965(12) 0.17647(16) 0.35252(6) 0.0497(3) Uani 1 1 d . . .
H14 H 0.4648 0.1674 0.3474 0.060 Uiso 1 1 calc R . .
C15 C 0.31581(13) 0.16909(18) -0.02256(7) 0.0571(4) Uani 1 1 d . . .
H15 H 0.3346 0.1612 -0.0667 0.068 Uiso 1 1 calc R . .
C16 C 0.34820(13) 0.17277(18) 0.41711(7) 0.0589(4) Uani 1 1 d . . .
H16 H 0.4121 0.1606 0.4553 0.071 Uiso 1 1 calc R . .
C17 C 0.67097(12) 0.34066(18) 0.12060(6) 0.0548(3) Uani 1 1 d . . .
H17 H 0.6191 0.4310 0.0949 0.066 Uiso 1 1 calc R . .
C18 C 0.87783(13) 0.2099(3) 0.15774(7) 0.0738(5) Uani 1 1 d . . .
H18 H 0.9652 0.2108 0.1573 0.089 Uiso 1 1 calc R . .
C19 C 0.69671(12) 0.0744(2) 0.19699(6) 0.0562(4) Uani 1 1 d . . .
H19 H 0.6628 -0.0151 0.2238 0.067 Uiso 1 1 calc R . .
C20 C 0.80055(13) 0.3420(2) 0.12062(7) 0.0665(4) Uani 1 1 d . . .
H20 H 0.8355 0.4338 0.0951 0.080 Uiso 1 1 calc R . .
C21 C 0.82630(13) 0.0756(2) 0.19567(7) 0.0710(4) Uani 1 1 d . . .
H21 H 0.8788 -0.0153 0.2207 0.085 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
N2 0.0355(6) 0.0486(6) 0.0421(6) -0.0011(5) 0.0042(5) 0.0019(4)
C2 0.0379(7) 0.0367(6) 0.0428(7) -0.0031(5) 0.0070(6) -0.0029(5)
N1 0.0327(6) 0.0512(6) 0.0429(6) -0.0011(5) 0.0059(5) -0.0004(4)
C3 0.0367(7) 0.0432(7) 0.0417(7) -0.0003(5) 0.0021(6) 0.0049(5)
C4 0.0341(7) 0.0361(6) 0.0451(7) -0.0008(5) 0.0055(6) 0.0002(5)
C5 0.0359(7) 0.0423(6) 0.0413(7) -0.0004(5) 0.0049(5) 0.0039(5)
C6 0.0341(7) 0.0420(7) 0.0429(7) -0.0001(5) 0.0056(5) 0.0019(5)
C7 0.0408(8) 0.0580(8) 0.0491(8) -0.0018(6) 0.0066(6) -0.0024(6)
C8 0.0422(8) 0.0646(8) 0.0457(7) -0.0011(6) 0.0089(6) 0.0047(6)
C9 0.0340(7) 0.0603(7) 0.0362(6) -0.0042(6) 0.0045(5) 0.0015(6)
C10 0.0484(8) 0.0665(9) 0.0606(9) -0.0044(7) 0.0227(7) -0.0050(6)
C11 0.0380(7) 0.0656(8) 0.0482(8) -0.0009(6) 0.0014(6) 0.0052(6)
C12 0.0663(10) 0.0654(9) 0.0454(8) -0.0035(7) 0.0174(7) -0.0094(7)
C13 0.0486(8) 0.0714(9) 0.0445(8) -0.0024(6) -0.0061(6) 0.0072(6)
C14 0.0402(7) 0.0616(8) 0.0465(7) -0.0019(6) 0.0055(6) -0.0019(6)
C15 0.0559(9) 0.0754(9) 0.0394(7) -0.0022(6) 0.0068(7) 0.0085(7)
C16 0.0571(9) 0.0744(9) 0.0434(8) -0.0019(7) 0.0030(7) -0.0063(7)
C17 0.0431(8) 0.0728(9) 0.0481(7) 0.0025(6) 0.0066(6) -0.0042(6)
C18 0.0326(7) 0.1465(15) 0.0429(8) -0.0112(9) 0.0081(7) -0.0017(9)
C19 0.0415(8) 0.0825(9) 0.0441(7) 0.0071(7) 0.0058(6) 0.0082(7)
C20 0.0440(9) 0.1105(12) 0.0455(8) -0.0003(8) 0.0092(7) -0.0193(8)
C21 0.0420(9) 0.1199(12) 0.0491(8) 0.0052(8) 0.0027(7) 0.0209(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
N2 C4 1.3109(14) . ?
N2 C3 1.3619(14) . ?
C2 C14 1.3808(15) . ?
C2 C7 1.3894(16) . ?
C2 C4 1.4857(15) . ?
N1 C6 1.3180(13) . ?
N1 C4 1.3674(14) . ?
C3 C11 1.4086(15) . ?
C3 C5 1.4127(16) . ?
C5 C8 1.4126(15) . ?
C5 C6 1.4228(15) . ?
C6 C9 1.4865(16) . ?
C7 C10 1.3762(16) . ?
C8 C15 1.3599(17) . ?
C9 C17 1.3842(16) . ?
C9 C19 1.3820(16) . ?
C10 C12 1.3649(18) . ?
C11 C13 1.3550(17) . ?
C12 C16 1.3740(19) . ?
C13 C15 1.4031(19) . ?
C14 C16 1.3750(17) . ?
C17 C20 1.3778(17) . ?
C18 C20 1.363(2) . ?
C18 C21 1.370(2) . ?
C19 C21 1.3827(18) . ?

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
C4 N2 C3 116.93(10) . . ?
C14 C2 C7 118.35(11) . . ?
C14 C2 C4 121.46(11) . . ?
C7 C2 C4 120.18(11) . . ?
C6 N1 C4 117.65(10) . . ?
N2 C3 C11 118.94(10) . . ?
N2 C3 C5 121.74(11) . . ?
C11 C3 C5 119.30(11) . . ?
N2 C4 N1 126.09(10) . . ?
N2 C4 C2 118.30(10) . . ?
N1 C4 C2 115.60(10) . . ?
C8 C5 C3 118.74(11) . . ?
C8 C5 C6 125.28(11) . . ?
C3 C5 C6 115.90(10) . . ?
N1 C6 C5 121.64(10) . . ?
N1 C6 C9 115.99(10) . . ?
C5 C6 C9 122.33(10) . . ?
C10 C7 C2 120.44(12) . . ?
C15 C8 C5 120.48(11) . . ?
C17 C9 C19 118.61(11) . . ?
C17 C9 C6 121.79(11) . . ?
C19 C9 C6 119.58(11) . . ?
C12 C10 C7 120.60(12) . . ?
C13 C11 C3 120.46(12) . . ?
C10 C12 C16 119.52(12) . . ?
C11 C13 C15 120.56(12) . . ?
C16 C14 C2 120.68(12) . . ?
C8 C15 C13 120.45(12) . . ?
C14 C16 C12 120.41(13) . . ?
C20 C17 C9 120.54(13) . . ?
C20 C18 C21 119.71(13) . . ?
C9 C19 C21 120.20(13) . . ?
C18 C20 C17 120.47(14) . . ?
C18 C21 C19 120.44(14) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.030