# 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              ?
loop_
_publ_author_name
'Qiang Wu'
'Pei Liu'
Y.Pan
'Yan-li Xu'
'Heng-shan Wang'
_publ_contact_author_name        Y.Pan
_publ_contact_author_email       panym2004@yahoo.com.cn

data_0628-pym-lp-p273-1
_database_code_depnum_ccdc_archive 'CCDC 891243'
#TrackingRef '- 4aa.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 N2'
_chemical_formula_sum            'C21 H18 N2'
_chemical_formula_weight         298.37

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   'P 21 '

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

_cell_length_a                   8.9304(9)
_cell_length_b                   5.9067(6)
_cell_length_c                   15.6236(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.614(9)
_cell_angle_gamma                90.00
_cell_volume                     822.50(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1331
_cell_measurement_theta_min      3.3555
_cell_measurement_theta_max      29.0585

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9825
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_process_details   ?

_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  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6251
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2845
_reflns_number_gt                1592
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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^)+(0.0400P)^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'
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2845
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.028
_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 0.0664(3) 0.6332(5) 0.27529(19) 0.0712(10) Uani 1 1 d . . .
C16 C -0.0129(4) 0.5158(7) 0.2100(2) 0.0597(10) Uani 1 1 d . . .
C10 C 0.2851(4) 0.8075(6) 0.2086(2) 0.0535(9) Uani 1 1 d . . .
N1 N 0.0985(3) 0.5321(5) 0.35397(18) 0.0653(9) Uani 1 1 d . . .
C17 C -0.0192(4) 0.5989(7) 0.1269(2) 0.0697(12) Uani 1 1 d . . .
H17 H 0.0293 0.7334 0.1148 0.084 Uiso 1 1 calc R . .
C7 C 0.1787(4) 0.6712(7) 0.4011(2) 0.0644(11) Uani 1 1 d . . .
C9 C 0.1545(4) 0.8383(6) 0.2644(2) 0.0621(10) Uani 1 1 d . . .
H9 H 0.0889 0.9587 0.2405 0.075 Uiso 1 1 calc R . .
C18 C -0.0979(4) 0.4812(8) 0.0617(2) 0.0760(12) Uani 1 1 d . . .
H18 H -0.1018 0.5369 0.0059 0.091 Uiso 1 1 calc R . .
C6 C 0.2363(4) 0.6118(7) 0.4885(2) 0.0673(11) Uani 1 1 d . . .
C21 C -0.0885(4) 0.3188(7) 0.2276(3) 0.0671(11) Uani 1 1 d . . .
H21 H -0.0876 0.2641 0.2835 0.080 Uiso 1 1 calc R . .
C3 C 0.3551(5) 0.4953(12) 0.6508(3) 0.0973(16) Uani 1 1 d . . .
H3 H 0.3968 0.4555 0.7048 0.117 Uiso 1 1 calc R . .
C15 C 0.3679(5) 0.6125(7) 0.2119(3) 0.0787(12) Uani 1 1 d . . .
H15 H 0.3402 0.4932 0.2464 0.094 Uiso 1 1 calc R . .
C20 C -0.1650(4) 0.2044(7) 0.1619(3) 0.0743(12) Uani 1 1 d . . .
H20 H -0.2146 0.0707 0.1739 0.089 Uiso 1 1 calc R . .
C19 C -0.1700(4) 0.2825(8) 0.0792(3) 0.0807(13) Uani 1 1 d . . .
H19 H -0.2215 0.2020 0.0355 0.097 Uiso 1 1 calc R . .
C1 C 0.1905(5) 0.4148(7) 0.5277(3) 0.0785(12) Uani 1 1 d . . .
H1 H 0.1196 0.3213 0.4995 0.094 Uiso 1 1 calc R . .
C8 C 0.2047(5) 0.8958(7) 0.3574(2) 0.0721(12) Uani 1 1 d . . .
H8A H 0.3095 0.9398 0.3630 0.086 Uiso 1 1 calc R . .
H8B H 0.1438 1.0152 0.3799 0.086 Uiso 1 1 calc R . .
C11 C 0.3263(5) 0.9799(8) 0.1556(3) 0.0734(11) Uani 1 1 d . . .
H11 H 0.2706 1.1130 0.1522 0.088 Uiso 1 1 calc R . .
C4 C 0.3976(6) 0.6893(10) 0.6133(3) 0.1046(18) Uani 1 1 d . . .
H4 H 0.4677 0.7827 0.6422 0.126 Uiso 1 1 calc R . .
C2 C 0.2503(6) 0.3569(9) 0.6092(3) 0.0935(15) Uani 1 1 d . . .
H2 H 0.2195 0.2250 0.6354 0.112 Uiso 1 1 calc R . .
C12 C 0.4506(6) 0.9557(11) 0.1073(3) 0.0961(17) Uani 1 1 d . . .
H12 H 0.4776 1.0716 0.0711 0.115 Uiso 1 1 calc R . .
C14 C 0.4916(6) 0.5918(10) 0.1646(4) 0.1020(17) Uani 1 1 d . . .
H14 H 0.5476 0.4590 0.1680 0.122 Uiso 1 1 calc R . .
C5 C 0.3385(5) 0.7521(8) 0.5321(3) 0.0841(14) Uani 1 1 d . . .
H5 H 0.3676 0.8872 0.5075 0.101 Uiso 1 1 calc R . .
C13 C 0.5332(6) 0.7608(13) 0.1133(4) 0.1064(19) Uani 1 1 d . . .
H13 H 0.6178 0.7450 0.0821 0.128 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 0.077(2) 0.084(3) 0.051(2) 0.0062(19) -0.0087(17) -0.019(2)
C16 0.049(2) 0.076(3) 0.053(2) -0.005(2) -0.0066(17) 0.003(2)
C10 0.056(2) 0.056(2) 0.048(2) -0.0034(19) -0.0081(18) -0.002(2)
N1 0.067(2) 0.077(2) 0.051(2) 0.0042(18) -0.0059(15) -0.0114(18)
C17 0.064(3) 0.088(3) 0.055(3) 0.001(2) -0.0076(19) -0.009(2)
C7 0.056(3) 0.082(3) 0.054(2) -0.007(2) 0.0019(19) 0.005(2)
C9 0.070(3) 0.059(2) 0.057(3) 0.001(2) -0.005(2) 0.000(2)
C18 0.066(3) 0.104(3) 0.057(3) -0.002(3) -0.007(2) -0.003(3)
C6 0.065(3) 0.086(3) 0.050(2) -0.007(2) -0.0016(19) 0.007(2)
C21 0.049(2) 0.081(3) 0.070(3) 0.001(2) -0.0074(19) -0.003(2)
C3 0.095(4) 0.138(5) 0.058(3) -0.003(4) -0.008(3) 0.041(4)
C15 0.071(3) 0.073(3) 0.092(3) -0.011(3) 0.004(2) 0.005(2)
C20 0.058(3) 0.080(3) 0.083(3) -0.005(3) -0.010(2) -0.003(2)
C19 0.067(3) 0.103(4) 0.070(3) -0.020(3) -0.012(2) -0.001(3)
C1 0.082(3) 0.094(3) 0.059(3) -0.002(3) 0.003(2) 0.000(3)
C8 0.083(3) 0.075(3) 0.057(2) -0.011(2) -0.003(2) -0.002(2)
C11 0.075(3) 0.079(3) 0.064(3) 0.001(3) -0.011(2) -0.010(2)
C4 0.106(4) 0.123(5) 0.080(4) -0.015(4) -0.028(3) 0.015(3)
C2 0.100(4) 0.116(4) 0.065(3) 0.012(3) 0.011(3) 0.017(3)
C12 0.094(4) 0.134(5) 0.060(3) 0.013(3) -0.002(3) -0.048(4)
C14 0.079(4) 0.106(4) 0.120(5) -0.036(4) 0.000(3) 0.015(3)
C5 0.087(3) 0.097(4) 0.066(3) -0.009(3) -0.016(2) -0.001(3)
C13 0.073(4) 0.159(6) 0.087(4) -0.046(4) 0.007(3) -0.022(4)

_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 N1 1.381(4) . ?
N2 C16 1.390(4) . ?
N2 C9 1.461(4) . ?
C16 C21 1.382(5) . ?
C16 C17 1.386(4) . ?
C10 C15 1.368(5) . ?
C10 C11 1.377(5) . ?
C10 C9 1.510(5) . ?
N1 C7 1.290(4) . ?
C17 C18 1.387(4) . ?
C17 H17 0.9300 . ?
C7 C6 1.471(5) . ?
C7 C8 1.516(5) . ?
C9 C8 1.533(5) . ?
C9 H9 0.9800 . ?
C18 C19 1.375(5) . ?
C18 H18 0.9300 . ?
C6 C5 1.380(5) . ?
C6 C1 1.389(5) . ?
C21 C20 1.374(5) . ?
C21 H21 0.9300 . ?
C3 C4 1.353(7) . ?
C3 C2 1.375(6) . ?
C3 H3 0.9300 . ?
C15 C14 1.373(6) . ?
C15 H15 0.9300 . ?
C20 C19 1.370(5) . ?
C20 H20 0.9300 . ?
C19 H19 0.9300 . ?
C1 C2 1.392(5) . ?
C1 H1 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C11 C12 1.388(6) . ?
C11 H11 0.9300 . ?
C4 C5 1.393(6) . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
C12 C13 1.367(7) . ?
C12 H12 0.9300 . ?
C14 C13 1.346(7) . ?
C14 H14 0.9300 . ?
C5 H5 0.9300 . ?
C13 H13 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
N1 N2 C16 120.4(3) . . ?
N1 N2 C9 112.3(3) . . ?
C16 N2 C9 125.5(3) . . ?
C21 C16 C17 119.6(3) . . ?
C21 C16 N2 120.4(3) . . ?
C17 C16 N2 120.0(3) . . ?
C15 C10 C11 118.8(4) . . ?
C15 C10 C9 121.0(4) . . ?
C11 C10 C9 120.2(3) . . ?
C7 N1 N2 108.0(3) . . ?
C16 C17 C18 120.0(4) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
N1 C7 C6 121.8(4) . . ?
N1 C7 C8 113.4(3) . . ?
C6 C7 C8 124.9(4) . . ?
N2 C9 C10 114.1(3) . . ?
N2 C9 C8 101.6(3) . . ?
C10 C9 C8 112.6(3) . . ?
N2 C9 H9 109.4 . . ?
C10 C9 H9 109.4 . . ?
C8 C9 H9 109.4 . . ?
C19 C18 C17 120.2(4) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C5 C6 C1 119.3(4) . . ?
C5 C6 C7 119.8(4) . . ?
C1 C6 C7 121.0(4) . . ?
C20 C21 C16 119.4(4) . . ?
C20 C21 H21 120.3 . . ?
C16 C21 H21 120.3 . . ?
C4 C3 C2 120.0(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C10 C15 C14 120.4(5) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C19 C20 C21 121.6(4) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C20 C19 C18 119.2(4) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C6 C1 C2 120.2(4) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C7 C8 C9 100.9(3) . . ?
C7 C8 H8A 111.6 . . ?
C9 C8 H8A 111.6 . . ?
C7 C8 H8B 111.6 . . ?
C9 C8 H8B 111.6 . . ?
H8A C8 H8B 109.4 . . ?
C10 C11 C12 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C3 C4 C5 121.3(5) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C3 C2 C1 119.8(5) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C13 C12 C11 119.7(5) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C13 C14 C15 121.0(5) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C6 C5 C4 119.4(5) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C14 C13 C12 119.8(5) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?

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
N1 N2 C16 C21 14.2(5) . . . . ?
C9 N2 C16 C21 177.8(3) . . . . ?
N1 N2 C16 C17 -167.2(3) . . . . ?
C9 N2 C16 C17 -3.6(5) . . . . ?
C16 N2 N1 C7 176.7(3) . . . . ?
C9 N2 N1 C7 11.1(4) . . . . ?
C21 C16 C17 C18 -1.7(5) . . . . ?
N2 C16 C17 C18 179.8(3) . . . . ?
N2 N1 C7 C6 -178.0(3) . . . . ?
N2 N1 C7 C8 2.4(4) . . . . ?
N1 N2 C9 C10 102.4(4) . . . . ?
C16 N2 C9 C10 -62.3(4) . . . . ?
N1 N2 C9 C8 -19.0(4) . . . . ?
C16 N2 C9 C8 176.3(3) . . . . ?
C15 C10 C9 N2 -37.6(4) . . . . ?
C11 C10 C9 N2 144.8(3) . . . . ?
C15 C10 C9 C8 77.5(4) . . . . ?
C11 C10 C9 C8 -100.1(4) . . . . ?
C16 C17 C18 C19 0.2(6) . . . . ?
N1 C7 C6 C5 171.0(4) . . . . ?
C8 C7 C6 C5 -9.5(5) . . . . ?
N1 C7 C6 C1 -8.4(6) . . . . ?
C8 C7 C6 C1 171.2(4) . . . . ?
C17 C16 C21 C20 2.0(5) . . . . ?
N2 C16 C21 C20 -179.4(4) . . . . ?
C11 C10 C15 C14 1.4(5) . . . . ?
C9 C10 C15 C14 -176.2(3) . . . . ?
C16 C21 C20 C19 -0.9(6) . . . . ?
C21 C20 C19 C18 -0.6(6) . . . . ?
C17 C18 C19 C20 1.0(6) . . . . ?
C5 C6 C1 C2 -1.8(6) . . . . ?
C7 C6 C1 C2 177.6(4) . . . . ?
N1 C7 C8 C9 -13.7(4) . . . . ?
C6 C7 C8 C9 166.8(3) . . . . ?
N2 C9 C8 C7 18.0(4) . . . . ?
C10 C9 C8 C7 -104.5(4) . . . . ?
C15 C10 C11 C12 -0.6(5) . . . . ?
C9 C10 C11 C12 177.0(3) . . . . ?
C2 C3 C4 C5 -0.8(8) . . . . ?
C4 C3 C2 C1 1.3(7) . . . . ?
C6 C1 C2 C3 0.0(6) . . . . ?
C10 C11 C12 C13 -0.7(6) . . . . ?
C10 C15 C14 C13 -0.8(7) . . . . ?
C1 C6 C5 C4 2.3(6) . . . . ?
C7 C6 C5 C4 -177.1(4) . . . . ?
C3 C4 C5 C6 -1.0(7) . . . . ?
C15 C14 C13 C12 -0.6(7) . . . . ?
C11 C12 C13 C14 1.4(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.028