# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd201531
_database_code_depnum_ccdc_archive 'CCDC 796953'
_audit_update_record             
;
2010-10-15 deposited with the CCDC.
2014-12-03 downloaded from the CCDC.
;
#TrackingRef '2827_web_deposit_cif_file_0_JunTang_1287155432.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 N2'
_chemical_formula_weight         322.39

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   P2(1)/c

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

_cell_length_a                   8.1644(9)
_cell_length_b                   10.1980(11)
_cell_length_c                   21.107(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.1510(10)
_cell_angle_gamma                90.00
_cell_volume                     1724.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3110
_cell_measurement_theta_min      4.452
_cell_measurement_theta_max      51.822

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.362
_exptl_crystal_size_min          0.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2993
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9136
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3370
_reflns_number_gt                2482
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0999P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3370
_refine_ls_number_parameters     231
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1697
_refine_ls_wR_factor_gt          0.1587
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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
N1 N 0.53959(18) 0.92741(15) 0.23298(6) 0.0608(4) Uani 1 1 d D . .
N2 N 0.33570(17) 1.24726(12) 0.13613(6) 0.0538(4) Uani 1 1 d . . .
C1 C 0.4123(2) 0.89150(15) 0.17771(7) 0.0519(4) Uani 1 1 d . . .
H1 H 0.3329 0.8338 0.1935 0.062 Uiso 1 1 calc R . .
C2 C 0.31793(18) 1.01310(15) 0.15102(7) 0.0477(4) Uani 1 1 d . . .
C3 C 0.40568(18) 1.13458(14) 0.15681(7) 0.0459(4) Uani 1 1 d . . .
C4 C 0.58254(19) 1.13609(14) 0.18768(7) 0.0478(4) Uani 1 1 d . . .
C5 C 0.64652(19) 1.02856(16) 0.22603(7) 0.0530(4) Uani 1 1 d . . .
C6 C 0.8111(2) 1.0307(2) 0.25825(8) 0.0722(5) Uani 1 1 d . . .
H6 H 0.8540 0.9604 0.2843 0.087 Uiso 1 1 calc R . .
C7 C 0.9109(2) 1.1356(3) 0.25189(10) 0.0831(6) Uani 1 1 d . . .
H7 H 1.0215 1.1359 0.2736 0.100 Uiso 1 1 calc R . .
C8 C 0.8497(2) 1.2405(2) 0.21391(11) 0.0794(6) Uani 1 1 d . . .
H8 H 0.9188 1.3112 0.2098 0.095 Uiso 1 1 calc R . .
C9 C 0.6860(2) 1.24103(17) 0.18181(9) 0.0610(5) Uani 1 1 d . . .
H9 H 0.6447 1.3122 0.1561 0.073 Uiso 1 1 calc R . .
C10 C 0.15396(19) 1.00933(17) 0.12030(7) 0.0553(4) Uani 1 1 d . . .
C11 C 0.0779(2) 1.12849(19) 0.09537(7) 0.0587(5) Uani 1 1 d . . .
C12 C 0.1723(2) 1.24493(17) 0.10524(7) 0.0573(5) Uani 1 1 d . . .
C13 C 0.0985(3) 1.3654(2) 0.08263(9) 0.0751(6) Uani 1 1 d . . .
H13 H 0.1603 1.4425 0.0893 0.090 Uiso 1 1 calc R . .
C14 C -0.0636(3) 1.3686(3) 0.05095(10) 0.0913(8) Uani 1 1 d . . .
H14 H -0.1125 1.4482 0.0365 0.110 Uiso 1 1 calc R . .
C15 C -0.1561(3) 1.2542(3) 0.04004(11) 0.0980(8) Uani 1 1 d . . .
H15 H -0.2659 1.2579 0.0176 0.118 Uiso 1 1 calc R . .
C16 C -0.0899(2) 1.1383(3) 0.06137(9) 0.0812(6) Uani 1 1 d . . .
H16 H -0.1549 1.0630 0.0538 0.097 Uiso 1 1 calc R . .
C17 C 0.0543(2) 0.8840(2) 0.11215(10) 0.0791(6) Uani 1 1 d . . .
H17A H 0.1264 0.8114 0.1270 0.119 Uiso 1 1 calc R . .
H17B H 0.0055 0.8719 0.0674 0.119 Uiso 1 1 calc R . .
H17C H -0.0326 0.8889 0.1369 0.119 Uiso 1 1 calc R . .
C18 C 0.48337(18) 0.81491(15) 0.12703(7) 0.0511(4) Uani 1 1 d . . .
C19 C 0.4940(3) 0.68111(19) 0.13073(11) 0.0919(7) Uani 1 1 d . . .
H19 H 0.4558 0.6378 0.1638 0.110 Uiso 1 1 calc R . .
C20 C 0.5603(4) 0.6092(2) 0.08633(12) 0.1135(10) Uani 1 1 d . . .
H20 H 0.5644 0.5182 0.0893 0.136 Uiso 1 1 calc R . .
C21 C 0.6198(3) 0.6710(2) 0.03800(10) 0.0831(6) Uani 1 1 d . . .
H21 H 0.6672 0.6229 0.0087 0.100 Uiso 1 1 calc R . .
C22 C 0.6092(2) 0.80294(18) 0.03324(9) 0.0650(5) Uani 1 1 d . . .
H22 H 0.6483 0.8457 0.0002 0.078 Uiso 1 1 calc R . .
C23 C 0.5406(2) 0.87481(15) 0.07704(8) 0.0571(4) Uani 1 1 d . . .
H23 H 0.5330 0.9655 0.0727 0.069 Uiso 1 1 calc R . .
H1A H 0.585(2) 0.8630(17) 0.2577(9) 0.084(6) Uiso 1 1 d D . .


_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
N1 C5 1.377(2) . ?
N1 C1 1.451(2) . ?
N1 H1A 0.877(15) . ?
N2 C3 1.3194(18) . ?
N2 C12 1.367(2) . ?
C1 C2 1.510(2) . ?
C1 C18 1.527(2) . ?
C1 H1 0.9800 . ?
C2 C10 1.371(2) . ?
C2 C3 1.424(2) . ?
C3 C4 1.465(2) . ?
C4 C9 1.383(2) . ?
C4 C5 1.403(2) . ?
C5 C6 1.384(2) . ?
C6 C7 1.367(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.419(2) . ?
C10 C17 1.507(2) . ?
C11 C12 1.409(2) . ?
C11 C16 1.422(2) . ?
C12 C13 1.410(2) . ?
C13 C14 1.363(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.341(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.369(2) . ?
C18 C23 1.377(2) . ?
C19 C20 1.380(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.366(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.350(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.380(2) . ?
C22 H22 0.9300 . ?
C23 H23 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
C5 N1 C1 118.26(13) . . ?
C5 N1 H1A 114.8(13) . . ?
C1 N1 H1A 116.5(13) . . ?
C3 N2 C12 117.57(14) . . ?
N1 C1 C2 109.09(13) . . ?
N1 C1 C18 112.46(12) . . ?
C2 C1 C18 113.22(12) . . ?
N1 C1 H1 107.3 . . ?
C2 C1 H1 107.3 . . ?
C18 C1 H1 107.3 . . ?
C10 C2 C3 119.61(14) . . ?
C10 C2 C1 122.31(14) . . ?
C3 C2 C1 118.06(13) . . ?
N2 C3 C2 123.41(14) . . ?
N2 C3 C4 117.68(14) . . ?
C2 C3 C4 118.91(13) . . ?
C9 C4 C5 119.40(15) . . ?
C9 C4 C3 122.30(14) . . ?
C5 C4 C3 118.27(14) . . ?
N1 C5 C6 122.31(16) . . ?
N1 C5 C4 118.30(14) . . ?
C6 C5 C4 119.30(16) . . ?
C7 C6 C5 120.29(19) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.76(18) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C9 119.97(19) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C4 120.28(18) . . ?
C8 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?
C2 C10 C11 117.95(15) . . ?
C2 C10 C17 122.30(15) . . ?
C11 C10 C17 119.74(15) . . ?
C12 C11 C10 118.66(14) . . ?
C12 C11 C16 117.46(18) . . ?
C10 C11 C16 123.88(18) . . ?
N2 C12 C11 122.72(14) . . ?
N2 C12 C13 117.36(17) . . ?
C11 C12 C13 119.92(18) . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 121.0(2) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 121.2(2) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 117.32(15) . . ?
C19 C18 C1 119.90(14) . . ?
C23 C18 C1 122.78(13) . . ?
C18 C19 C20 121.32(19) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C21 C20 C19 120.30(19) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 119.22(18) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C23 120.51(17) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C18 C23 C22 121.29(15) . . ?
C18 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?

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 C1 C2 -51.21(18) . . . . ?
C5 N1 C1 C18 75.26(18) . . . . ?
N1 C1 C2 C10 -150.44(14) . . . . ?
C18 C1 C2 C10 83.52(17) . . . . ?
N1 C1 C2 C3 31.33(17) . . . . ?
C18 C1 C2 C3 -94.71(16) . . . . ?
C12 N2 C3 C2 -2.8(2) . . . . ?
C12 N2 C3 C4 177.67(12) . . . . ?
C10 C2 C3 N2 2.7(2) . . . . ?
C1 C2 C3 N2 -179.01(13) . . . . ?
C10 C2 C3 C4 -177.78(13) . . . . ?
C1 C2 C3 C4 0.49(19) . . . . ?
N2 C3 C4 C9 -16.2(2) . . . . ?
C2 C3 C4 C9 164.29(14) . . . . ?
N2 C3 C4 C5 161.81(13) . . . . ?
C2 C3 C4 C5 -17.72(19) . . . . ?
C1 N1 C5 C6 -146.71(16) . . . . ?
C1 N1 C5 C4 36.9(2) . . . . ?
C9 C4 C5 N1 177.70(14) . . . . ?
C3 C4 C5 N1 -0.3(2) . . . . ?
C9 C4 C5 C6 1.2(2) . . . . ?
C3 C4 C5 C6 -176.82(13) . . . . ?
N1 C5 C6 C7 -177.37(16) . . . . ?
C4 C5 C6 C7 -1.0(2) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C4 0.0(3) . . . . ?
C5 C4 C9 C8 -0.7(2) . . . . ?
C3 C4 C9 C8 177.25(14) . . . . ?
C3 C2 C10 C11 -0.1(2) . . . . ?
C1 C2 C10 C11 -178.28(13) . . . . ?
C3 C2 C10 C17 179.61(14) . . . . ?
C1 C2 C10 C17 1.4(2) . . . . ?
C2 C10 C11 C12 -2.1(2) . . . . ?
C17 C10 C11 C12 178.19(15) . . . . ?
C2 C10 C11 C16 178.70(14) . . . . ?
C17 C10 C11 C16 -1.0(2) . . . . ?
C3 N2 C12 C11 0.4(2) . . . . ?
C3 N2 C12 C13 -179.35(13) . . . . ?
C10 C11 C12 N2 2.1(2) . . . . ?
C16 C11 C12 N2 -178.71(14) . . . . ?
C10 C11 C12 C13 -178.18(14) . . . . ?
C16 C11 C12 C13 1.1(2) . . . . ?
N2 C12 C13 C14 179.39(16) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 C16 1.3(3) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C12 C11 C16 C15 -0.6(3) . . . . ?
C10 C11 C16 C15 178.62(18) . . . . ?
N1 C1 C18 C19 89.1(2) . . . . ?
C2 C1 C18 C19 -146.67(17) . . . . ?
N1 C1 C18 C23 -90.05(18) . . . . ?
C2 C1 C18 C23 34.2(2) . . . . ?
C23 C18 C19 C20 0.3(3) . . . . ?
C1 C18 C19 C20 -178.9(2) . . . . ?
C18 C19 C20 C21 1.2(4) . . . . ?
C19 C20 C21 C22 -1.7(4) . . . . ?
C20 C21 C22 C23 0.7(3) . . . . ?
C19 C18 C23 C22 -1.3(3) . . . . ?
C1 C18 C23 C22 177.86(15) . . . . ?
C21 C22 C23 C18 0.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.055



