# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_zj
_database_code_depnum_ccdc_archive 'CCDC 1047287'
_audit_update_record             
;
2015-02-04 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H23 N'
_chemical_formula_weight         349.45

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           ?
_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                   15.205(3)
_cell_length_b                   7.3621(15)
_cell_length_c                   18.007(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.56(3)
_cell_angle_gamma                90.00
_cell_volume                     2002.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  ?
_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            29812
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4563
_reflns_number_gt                3440
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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 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)+(0.1078P)²+0.1785P] 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     SHELXL
_refine_ls_extinction_coef       0.027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4563
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1620
_refine_ls_wR_factor_gt          0.1417
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      0.942
_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 0.22277(7) -0.06557(15) 0.10695(6) 0.0490(3) Uani 1 1 d . . .
C8 C 0.12445(8) 0.07490(17) 0.17024(6) 0.0448(3) Uani 1 1 d . . .
C11 C 0.28326(9) -0.11139(17) 0.05491(7) 0.0486(3) Uani 1 1 d . . .
C9 C 0.15727(9) -0.08147(18) 0.21170(7) 0.0491(3) Uani 1 1 d . . .
C10 C 0.21687(9) -0.16172(19) 0.17178(7) 0.0531(3) Uani 1 1 d . . .
H10A H 0.2490 -0.2660 0.1860 0.064 Uiso 1 1 calc R . .
C1 C 0.15503(9) 0.21372(17) 0.04367(7) 0.0498(3) Uani 1 1 d . . .
C17 C 0.06358(8) 0.21388(18) 0.19482(6) 0.0470(3) Uani 1 1 d . . .
C19 C -0.02143(8) 0.15127(18) 0.21931(7) 0.0487(3) Uani 1 1 d . . .
C7 C 0.16561(8) 0.08129(16) 0.10539(7) 0.0450(3) Uani 1 1 d . . .
C20 C -0.06197(9) 0.2437(2) 0.27413(8) 0.0597(4) Uani 1 1 d . . .
H20A H -0.0353 0.3473 0.2960 0.072 Uiso 1 1 calc R . .
C16 C 0.25942(10) -0.10240(19) -0.02148(7) 0.0551(3) Uani 1 1 d . . .
H16A H 0.2025 -0.0672 -0.0403 0.066 Uiso 1 1 calc R . .
C25 C 0.13423(11) -0.1447(2) 0.28612(8) 0.0632(4) Uani 1 1 d . . .
H25A H 0.1662 -0.2541 0.3002 0.095 Uiso 1 1 calc R . .
H25B H 0.0718 -0.1681 0.2829 0.095 Uiso 1 1 calc R . .
H25C H 0.1499 -0.0524 0.3229 0.095 Uiso 1 1 calc R . .
C12 C 0.36735(10) -0.1664(2) 0.08210(8) 0.0619(4) Uani 1 1 d . . .
H12A H 0.3839 -0.1723 0.1334 0.074 Uiso 1 1 calc R . .
C15 C 0.32105(11) -0.1462(2) -0.06969(8) 0.0620(4) Uani 1 1 d . . .
H15A H 0.3049 -0.1382 -0.1210 0.074 Uiso 1 1 calc R . .
C18 C 0.08501(12) 0.3893(2) 0.19507(8) 0.0618(4) Uani 1 1 d . . .
C14 C 0.40581(11) -0.2015(2) -0.04368(9) 0.0620(4) Uani 1 1 d . . .
C24 C -0.06378(9) -0.0015(2) 0.18823(8) 0.0600(4) Uani 1 1 d . . .
H24A H -0.0382 -0.0664 0.1519 0.072 Uiso 1 1 calc R . .
C6 C 0.22735(12) 0.3072(2) 0.02162(9) 0.0638(4) Uani 1 1 d . . .
H6A H 0.2837 0.2862 0.0459 0.077 Uiso 1 1 calc R . .
C21 C -0.14073(11) 0.1840(3) 0.29635(10) 0.0732(5) Uani 1 1 d . . .
H21A H -0.1663 0.2469 0.3332 0.088 Uiso 1 1 calc R . .
C2 C 0.07161(11) 0.2476(2) 0.00668(8) 0.0641(4) Uani 1 1 d . . .
H2A H 0.0227 0.1859 0.0205 0.077 Uiso 1 1 calc R . .
C22 C -0.18173(10) 0.0318(3) 0.26429(10) 0.0780(5) Uani 1 1 d . . .
H22A H -0.2349 -0.0086 0.2792 0.094 Uiso 1 1 calc R . .
C23 C -0.14315(10) -0.0594(3) 0.21003(10) 0.0736(5) Uani 1 1 d . . .
H23A H -0.1708 -0.1615 0.1877 0.088 Uiso 1 1 calc R . .
C13 C 0.42735(11) -0.2130(3) 0.03280(9) 0.0693(4) Uani 1 1 d . . .
H13A H 0.4835 -0.2530 0.0517 0.083 Uiso 1 1 calc R . .
C4 C 0.1328(2) 0.4643(3) -0.07233(10) 0.0971(7) Uani 1 1 d . . .
H4A H 0.1253 0.5483 -0.1111 0.117 Uiso 1 1 calc R . .
C3 C 0.06115(16) 0.3733(3) -0.05099(9) 0.0865(6) Uani 1 1 d . . .
H3A H 0.0050 0.3961 -0.0754 0.104 Uiso 1 1 calc R . .
C5 C 0.21555(18) 0.4309(2) -0.03614(10) 0.0875(6) Uani 1 1 d . . .
H5A H 0.2642 0.4922 -0.0507 0.105 Uiso 1 1 calc R . .
C26 C 0.47220(13) -0.2502(3) -0.09639(11) 0.0862(6) Uani 1 1 d . . .
H26A H 0.5271 -0.2846 -0.0681 0.129 Uiso 1 1 calc R . .
H26B H 0.4818 -0.1473 -0.1272 0.129 Uiso 1 1 calc R . .
H26C H 0.4500 -0.3499 -0.1274 0.129 Uiso 1 1 calc R . .
H18A H 0.1429(12) 0.432(2) 0.1797(8) 0.064(4) Uiso 1 1 d . . .
H18B H 0.0400(12) 0.477(3) 0.2102(10) 0.078(5) Uiso 1 1 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 C10 1.3769(16) . ?
N1 C7 1.3855(16) . ?
N1 C11 1.4265(16) . ?
C8 C7 1.3873(16) . ?
C8 C9 1.4306(18) . ?
C8 C17 1.4808(17) . ?
C11 C12 1.377(2) . ?
C11 C16 1.3834(18) . ?
C9 C10 1.3549(18) . ?
C9 C25 1.4976(17) . ?
C1 C2 1.386(2) . ?
C1 C6 1.393(2) . ?
C1 C7 1.4733(17) . ?
C17 C18 1.332(2) . ?
C17 C19 1.4860(18) . ?
C19 C24 1.382(2) . ?
C19 C20 1.3987(18) . ?
C20 C21 1.377(2) . ?
C16 C15 1.3863(19) . ?
C12 C13 1.387(2) . ?
C15 C14 1.381(2) . ?
C14 C13 1.381(2) . ?
C14 C26 1.506(2) . ?
C24 C23 1.379(2) . ?
C6 C5 1.378(2) . ?
C21 C22 1.377(3) . ?
C2 C3 1.387(2) . ?
C22 C23 1.371(2) . ?
C4 C3 1.371(3) . ?
C4 C5 1.372(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 N1 C7 108.48(10) . . ?
C10 N1 C11 123.01(11) . . ?
C7 N1 C11 128.40(10) . . ?
C7 C8 C9 107.61(11) . . ?
C7 C8 C17 125.84(11) . . ?
C9 C8 C17 126.35(11) . . ?
C12 C11 C16 119.66(13) . . ?
C12 C11 N1 118.56(12) . . ?
C16 C11 N1 121.77(12) . . ?
C10 C9 C8 106.78(11) . . ?
C10 C9 C25 125.33(13) . . ?
C8 C9 C25 127.87(12) . . ?
C9 C10 N1 109.75(12) . . ?
C2 C1 C6 118.87(13) . . ?
C2 C1 C7 119.77(13) . . ?
C6 C1 C7 121.36(13) . . ?
C18 C17 C8 120.67(13) . . ?
C18 C17 C19 121.37(13) . . ?
C8 C17 C19 117.97(11) . . ?
C24 C19 C20 117.33(13) . . ?
C24 C19 C17 120.87(11) . . ?
C20 C19 C17 121.81(13) . . ?
C8 C7 N1 107.38(10) . . ?
C8 C7 C1 129.53(11) . . ?
N1 C7 C1 123.09(11) . . ?
C21 C20 C19 121.18(15) . . ?
C11 C16 C15 119.50(14) . . ?
C11 C12 C13 119.81(14) . . ?
C16 C15 C14 121.84(14) . . ?
C13 C14 C15 117.51(13) . . ?
C13 C14 C26 120.94(16) . . ?
C15 C14 C26 121.54(15) . . ?
C23 C24 C19 121.26(14) . . ?
C5 C6 C1 120.17(18) . . ?
C20 C21 C22 120.33(15) . . ?
C1 C2 C3 120.02(18) . . ?
C23 C22 C21 119.17(16) . . ?
C22 C23 C24 120.72(17) . . ?
C14 C13 C12 121.65(15) . . ?
C3 C4 C5 119.61(16) . . ?
C4 C3 C2 120.63(19) . . ?
C4 C5 C6 120.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.036
