# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'RSC Advances'
_journal_coden_cambridge         1500
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       chenma@sdu.edu.cn
_publ_contact_author_name        'Chen Ma'
loop_
_publ_author_name
'Chunjing Zhan'
'Jiong Jia'
'Bingchuan Yang'
'Aiping Huang'
'Yanli Liu'
'Chen Ma'

data_test
_database_code_depnum_ccdc_archive 'CCDC 864981'
#TrackingRef 'C2RA20334K.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 N O2'
_chemical_formula_weight         253.29

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           ?
_symmetry_space_group_name_H-M   ?

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                   11.718(3)
_cell_length_b                   5.5721(13)
_cell_length_c                   20.637(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.252(2)
_cell_angle_gamma                90.00
_cell_volume                     1306.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9915
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(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            10455
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         27.51
_reflns_number_total             2978
_reflns_number_gt                2352
_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^)+(0.0717P)^2^+0.2653P] 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         2978
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.004

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 0.44613(10) 0.6981(2) -0.07066(6) 0.0652(4) Uani 1 1 d . . .
O2 O 0.72521(10) 0.9301(2) 0.01293(5) 0.0530(3) Uani 1 1 d . . .
N1 N 0.54440(10) 1.0172(2) -0.09854(5) 0.0397(3) Uani 1 1 d . . .
C11 C 0.65451(11) 1.1312(2) -0.09214(6) 0.0374(3) Uani 1 1 d . . .
C12 C 0.67558(12) 1.2920(2) -0.13946(7) 0.0410(3) Uani 1 1 d . . .
H12A H 0.6172 1.3190 -0.1784 0.049 Uiso 1 1 calc R . .
C6 C 0.42246(11) 1.0224(2) -0.21687(7) 0.0393(3) Uani 1 1 d . . .
C10 C 0.74428(13) 1.0838(3) -0.03525(7) 0.0439(3) Uani 1 1 d . . .
C7 C 0.43854(12) 1.1079(3) -0.14562(7) 0.0421(3) Uani 1 1 d . . .
H7A H 0.4413 1.2819 -0.1452 0.051 Uiso 1 1 calc R . .
H7B H 0.3703 1.0598 -0.1301 0.051 Uiso 1 1 calc R . .
C13 C 0.78215(13) 1.4131(3) -0.12980(8) 0.0480(4) Uani 1 1 d . . .
C15 C 0.85070(14) 1.2008(3) -0.02549(8) 0.0568(4) Uani 1 1 d . . .
H15A H 0.9103 1.1696 0.0126 0.068 Uiso 1 1 calc R . .
C8 C 0.53621(13) 0.8156(3) -0.06251(7) 0.0442(3) Uani 1 1 d . . .
C16 C 0.80116(16) 1.5977(3) -0.17964(9) 0.0643(5) Uani 1 1 d . . .
H16A H 0.8791 1.6630 -0.1651 0.096 Uiso 1 1 calc R . .
H16B H 0.7444 1.7241 -0.1830 0.096 Uiso 1 1 calc R . .
H16C H 0.7921 1.5232 -0.2226 0.096 Uiso 1 1 calc R . .
C14 C 0.86888(14) 1.3647(3) -0.07238(9) 0.0585(4) Uani 1 1 d . . .
H14A H 0.9408 1.4438 -0.0652 0.070 Uiso 1 1 calc R . .
C9 C 0.64706(14) 0.7385(3) -0.01320(7) 0.0476(4) Uani 1 1 d . . .
H9A H 0.6259 0.6566 0.0237 0.057 Uiso 1 1 calc R . .
H9B H 0.6881 0.6242 -0.0348 0.057 Uiso 1 1 calc R . .
C1 C 0.47193(15) 0.8126(3) -0.23230(8) 0.0534(4) Uani 1 1 d . . .
H1A H 0.5207 0.7232 -0.1985 0.064 Uiso 1 1 calc R . .
C5 C 0.35077(13) 1.1527(3) -0.26822(8) 0.0566(4) Uani 1 1 d . . .
H5A H 0.3172 1.2955 -0.2587 0.068 Uiso 1 1 calc R . .
C3 C 0.37798(16) 0.8641(4) -0.34829(9) 0.0712(6) Uani 1 1 d . . .
H3A H 0.3631 0.8108 -0.3923 0.085 Uiso 1 1 calc R . .
C4 C 0.32863(16) 1.0729(4) -0.33344(9) 0.0730(6) Uani 1 1 d . . .
H4A H 0.2799 1.1616 -0.3674 0.088 Uiso 1 1 calc R . .
C2 C 0.44941(18) 0.7338(4) -0.29805(9) 0.0687(5) Uani 1 1 d . . .
H2A H 0.4830 0.5917 -0.3080 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
O1 0.0571(7) 0.0647(7) 0.0706(8) 0.0169(6) 0.0096(6) -0.0148(6)
O2 0.0625(7) 0.0538(6) 0.0360(5) 0.0050(4) -0.0005(4) -0.0042(5)
N1 0.0406(6) 0.0395(6) 0.0361(5) 0.0010(5) 0.0039(4) -0.0009(5)
C11 0.0405(7) 0.0352(6) 0.0357(6) -0.0050(5) 0.0078(5) 0.0004(5)
C12 0.0457(7) 0.0386(7) 0.0380(7) -0.0011(5) 0.0091(6) 0.0026(6)
C6 0.0326(6) 0.0413(7) 0.0417(7) 0.0000(5) 0.0047(5) -0.0048(5)
C10 0.0466(7) 0.0447(8) 0.0376(7) 0.0002(6) 0.0049(6) 0.0024(6)
C7 0.0386(7) 0.0419(7) 0.0440(7) -0.0013(6) 0.0067(6) 0.0034(6)
C13 0.0499(8) 0.0446(8) 0.0526(8) -0.0022(6) 0.0189(7) -0.0013(6)
C15 0.0441(8) 0.0666(10) 0.0524(9) -0.0001(8) -0.0019(7) -0.0022(7)
C8 0.0509(8) 0.0434(7) 0.0385(7) 0.0001(6) 0.0117(6) -0.0030(6)
C16 0.0661(11) 0.0585(10) 0.0749(12) 0.0088(9) 0.0296(9) -0.0060(8)
C14 0.0427(8) 0.0644(10) 0.0668(10) -0.0021(8) 0.0108(7) -0.0095(7)
C9 0.0595(9) 0.0431(7) 0.0389(7) 0.0039(6) 0.0092(6) 0.0015(7)
C1 0.0632(9) 0.0464(8) 0.0489(8) -0.0020(7) 0.0107(7) 0.0039(7)
C5 0.0447(8) 0.0672(10) 0.0527(9) 0.0069(8) 0.0022(7) 0.0109(7)
C3 0.0592(10) 0.1070(16) 0.0446(9) -0.0192(10) 0.0073(8) -0.0245(11)
C4 0.0515(9) 0.1128(17) 0.0456(9) 0.0097(10) -0.0054(7) 0.0024(10)
C2 0.0828(13) 0.0623(10) 0.0633(11) -0.0202(9) 0.0225(9) -0.0080(9)

_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 C8 1.2179(18) . ?
O2 C10 1.3717(17) . ?
O2 C9 1.4233(18) . ?
N1 C8 1.3636(18) . ?
N1 C11 1.4149(17) . ?
N1 C7 1.4645(17) . ?
C11 C12 1.3915(19) . ?
C11 C10 1.3952(19) . ?
C12 C13 1.390(2) . ?
C6 C1 1.376(2) . ?
C6 C5 1.385(2) . ?
C6 C7 1.5126(19) . ?
C10 C15 1.377(2) . ?
C13 C14 1.385(2) . ?
C13 C16 1.509(2) . ?
C15 C14 1.385(2) . ?
C8 C9 1.502(2) . ?
C1 C2 1.388(2) . ?
C5 C4 1.380(2) . ?
C3 C2 1.369(3) . ?
C3 C4 1.368(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
C10 O2 C9 113.47(10) . . ?
C8 N1 C11 120.26(11) . . ?
C8 N1 C7 118.96(12) . . ?
C11 N1 C7 120.74(11) . . ?
C12 C11 C10 119.02(13) . . ?
C12 C11 N1 122.61(12) . . ?
C10 C11 N1 118.35(12) . . ?
C13 C12 C11 121.35(13) . . ?
C1 C6 C5 118.62(14) . . ?
C1 C6 C7 122.25(13) . . ?
C5 C6 C7 119.05(13) . . ?
O2 C10 C15 119.52(13) . . ?
O2 C10 C11 120.30(13) . . ?
C15 C10 C11 120.10(14) . . ?
N1 C7 C6 114.75(11) . . ?
C14 C13 C12 118.20(14) . . ?
C14 C13 C16 121.04(15) . . ?
C12 C13 C16 120.73(14) . . ?
C10 C15 C14 119.97(14) . . ?
O1 C8 N1 122.84(13) . . ?
O1 C8 C9 121.03(13) . . ?
N1 C8 C9 116.09(12) . . ?
C13 C14 C15 121.32(15) . . ?
O2 C9 C8 114.24(12) . . ?
C6 C1 C2 120.34(16) . . ?
C4 C5 C6 120.69(17) . . ?
C2 C3 C4 119.65(16) . . ?
C3 C4 C5 120.29(17) . . ?
C3 C2 C1 120.40(18) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.036