# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_e:\140304g\work\t
_database_code_depnum_ccdc_archive 'CCDC 1030461'
_audit_update_record             
;
2014-10-22 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 N2'
_chemical_formula_weight         350.45

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           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                   9.4408(17)
_cell_length_b                   25.506(5)
_cell_length_c                   8.0660(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.641(4)
_cell_angle_gamma                90.00
_cell_volume                     1932.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1801
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      21.44

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      1.204
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9916
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12169
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3388
_reflns_number_gt                2132
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0599P)²+0.2980P] 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       0.0019(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3388
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1367
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.098
_refine_ls_shift/su_mean         0.002

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
C23 C 0.2554(3) 0.55509(10) 0.9143(3) 0.0705(7) Uani 1 1 d . . .
H23 H 0.2476 0.5830 0.9871 0.085 Uiso 1 1 calc R . .
C22 C 0.3891(3) 0.54080(10) 0.8714(3) 0.0688(7) Uani 1 1 d . . .
H22 H 0.4689 0.5591 0.9167 0.083 Uiso 1 1 calc R . .
C21 C 0.4056(2) 0.50000(9) 0.7628(3) 0.0577(6) Uani 1 1 d . . .
H21 H 0.4956 0.4909 0.7347 0.069 Uiso 1 1 calc R . .
C18 C 0.1201(2) 0.42073(9) 0.5646(3) 0.0517(6) Uani 1 1 d . . .
H18 H 0.0749 0.3951 0.4966 0.062 Uiso 1 1 calc R . .
C24 C 0.1344(3) 0.52892(9) 0.8515(3) 0.0619(7) Uani 1 1 d . . .
H24 H 0.0451 0.5385 0.8805 0.074 Uiso 1 1 calc R . .
C7 C 0.2512(2) 0.39630(10) 0.1988(3) 0.0592(6) Uani 1 1 d . . .
H7 H 0.2647 0.4323 0.1901 0.071 Uiso 1 1 calc R . .
C6 C 0.1785(3) 0.36971(13) 0.0678(3) 0.0710(7) Uani 1 1 d . . .
H6 H 0.1422 0.3878 -0.0271 0.085 Uiso 1 1 calc R . .
C9 C 0.4560(2) 0.35422(9) 0.7659(3) 0.0545(6) Uani 1 1 d . . .
H9 H 0.3753 0.3613 0.8196 0.065 Uiso 1 1 calc R . .
C17 C 0.2626(2) 0.42969(8) 0.5807(3) 0.0458(5) Uani 1 1 d . . .
C1 C 0.3744(2) 0.40182(8) 0.4919(3) 0.0470(5) Uani 1 1 d . . .
H1 H 0.4318 0.4292 0.4456 0.056 Uiso 1 1 calc R . .
C8 C 0.4745(2) 0.37016(8) 0.6090(3) 0.0460(5) Uani 1 1 d . . .
N2 N 0.05149(17) 0.45477(7) 0.6627(2) 0.0527(5) Uani 1 1 d . . .
C19 C 0.1511(2) 0.48738(8) 0.7426(3) 0.0496(5) Uani 1 1 d . . .
C25 C -0.1013(2) 0.45628(10) 0.6737(3) 0.0650(7) Uani 1 1 d . . .
H25A H -0.1371 0.4211 0.6783 0.098 Uiso 1 1 calc R . .
H25B H -0.1470 0.4738 0.5776 0.098 Uiso 1 1 calc R . .
H25C H -0.1205 0.4749 0.7725 0.098 Uiso 1 1 calc R . .
C2 C 0.3047(2) 0.37052(9) 0.3436(3) 0.0480(5) Uani 1 1 d . . .
C3 C 0.2859(3) 0.31683(10) 0.3506(3) 0.0644(7) Uani 1 1 d . . .
H3 H 0.3217 0.2985 0.4451 0.077 Uiso 1 1 calc R . .
N1 N 0.5714(2) 0.32631(7) 0.8354(2) 0.0572(5) Uani 1 1 d . . .
C20 C 0.2856(2) 0.47256(8) 0.6957(3) 0.0466(5) Uani 1 1 d . . .
C11 C 0.6115(2) 0.35076(8) 0.5757(3) 0.0448(5) Uani 1 1 d . . .
C12 C 0.6909(2) 0.35333(9) 0.4384(3) 0.0547(6) Uani 1 1 d . . .
H12 H 0.6549 0.3706 0.3418 0.066 Uiso 1 1 calc R . .
C13 C 0.8222(2) 0.33006(10) 0.4480(4) 0.0664(7) Uani 1 1 d . . .
H13 H 0.8751 0.3316 0.3568 0.080 Uiso 1 1 calc R . .
C14 C 0.8777(3) 0.30430(10) 0.5914(4) 0.0718(8) Uani 1 1 d . . .
H14 H 0.9675 0.2892 0.5945 0.086 Uiso 1 1 calc R . .
C5 C 0.1600(3) 0.31625(14) 0.0781(4) 0.0800(8) Uani 1 1 d . . .
H5 H 0.1108 0.2981 -0.0095 0.096 Uiso 1 1 calc R . .
C4 C 0.2144(3) 0.29007(12) 0.2184(4) 0.0814(8) Uani 1 1 d . . .
H4 H 0.2033 0.2539 0.2249 0.098 Uiso 1 1 calc R . .
C16 C 0.5850(3) 0.30156(11) 0.9985(3) 0.0804(8) Uani 1 1 d . . .
H16A H 0.5851 0.2642 0.9854 0.121 Uiso 1 1 calc R . .
H16B H 0.5063 0.3117 1.0582 0.121 Uiso 1 1 calc R . .
H16C H 0.6725 0.3124 1.0595 0.121 Uiso 1 1 calc R . .
C10 C 0.6692(2) 0.32383(8) 0.7200(3) 0.0491(6) Uani 1 1 d . . .
C15 C 0.8030(2) 0.30060(9) 0.7293(4) 0.0652(7) Uani 1 1 d . . .
H15 H 0.8406 0.2832 0.8251 0.078 Uiso 1 1 calc R . .


_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
C23 C24 1.376(3) . ?
C23 C22 1.389(4) . ?
C23 H23 0.9300 . ?
C22 C21 1.379(3) . ?
C22 H22 0.9300 . ?
C21 C20 1.395(3) . ?
C21 H21 0.9300 . ?
C18 C17 1.358(3) . ?
C18 N2 1.378(3) . ?
C18 H18 0.9300 . ?
C24 C19 1.395(3) . ?
C24 H24 0.9300 . ?
C7 C6 1.381(3) . ?
C7 C2 1.391(3) . ?
C7 H7 0.9300 . ?
C6 C5 1.378(4) . ?
C6 H6 0.9300 . ?
C9 C8 1.357(3) . ?
C9 N1 1.374(3) . ?
C9 H9 0.9300 . ?
C17 C20 1.437(3) . ?
C17 C1 1.510(3) . ?
C1 C8 1.504(3) . ?
C1 C2 1.532(3) . ?
C1 H1 0.9800 . ?
C8 C11 1.434(3) . ?
N2 C19 1.369(3) . ?
N2 C25 1.454(3) . ?
C19 C20 1.411(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C2 C3 1.382(3) . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
N1 C10 1.376(3) . ?
N1 C16 1.453(3) . ?
C11 C12 1.398(3) . ?
C11 C10 1.413(3) . ?
C12 C13 1.370(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C5 C4 1.369(4) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C10 C15 1.390(3) . ?
C15 H15 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
C24 C23 C22 121.5(2) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C21 C22 C23 121.2(2) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C22 C21 C20 119.1(2) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C17 C18 N2 110.87(19) . . ?
C17 C18 H18 124.6 . . ?
N2 C18 H18 124.6 . . ?
C23 C24 C19 117.3(2) . . ?
C23 C24 H24 121.3 . . ?
C19 C24 H24 121.3 . . ?
C6 C7 C2 121.5(3) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
C5 C6 C7 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C9 N1 111.5(2) . . ?
C8 C9 H9 124.3 . . ?
N1 C9 H9 124.3 . . ?
C18 C17 C20 105.94(18) . . ?
C18 C17 C1 127.4(2) . . ?
C20 C17 C1 126.61(18) . . ?
C8 C1 C17 112.39(18) . . ?
C8 C1 C2 113.93(18) . . ?
C17 C1 C2 110.44(16) . . ?
C8 C1 H1 106.5 . . ?
C17 C1 H1 106.5 . . ?
C2 C1 H1 106.5 . . ?
C9 C8 C11 105.82(18) . . ?
C9 C8 C1 127.98(19) . . ?
C11 C8 C1 126.20(19) . . ?
C19 N2 C18 108.25(17) . . ?
C19 N2 C25 126.52(19) . . ?
C18 N2 C25 125.20(19) . . ?
N2 C19 C24 130.0(2) . . ?
N2 C19 C20 107.79(19) . . ?
C24 C19 C20 122.2(2) . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C3 C2 C7 117.7(2) . . ?
C3 C2 C1 122.1(2) . . ?
C7 C2 C1 120.1(2) . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C9 N1 C10 107.79(18) . . ?
C9 N1 C16 126.2(2) . . ?
C10 N1 C16 126.0(2) . . ?
C21 C20 C19 118.6(2) . . ?
C21 C20 C17 134.2(2) . . ?
C19 C20 C17 107.13(18) . . ?
C12 C11 C10 118.78(19) . . ?
C12 C11 C8 134.0(2) . . ?
C10 C11 C8 107.19(19) . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 121.2(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 121.6(2) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C10 C15 130.5(2) . . ?
N1 C10 C11 107.74(18) . . ?
C15 C10 C11 121.8(2) . . ?
C14 C15 C10 117.5(2) . . ?
C14 C15 H15 121.3 . . ?
C10 C15 H15 121.3 . . ?

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
C24 C23 C22 C21 0.5(4) . . . . ?
C23 C22 C21 C20 -0.3(4) . . . . ?
C22 C23 C24 C19 -0.1(4) . . . . ?
C2 C7 C6 C5 -1.1(4) . . . . ?
N2 C18 C17 C20 -0.5(2) . . . . ?
N2 C18 C17 C1 -178.6(2) . . . . ?
C18 C17 C1 C8 -113.6(2) . . . . ?
C20 C17 C1 C8 68.7(3) . . . . ?
C18 C17 C1 C2 14.9(3) . . . . ?
C20 C17 C1 C2 -162.9(2) . . . . ?
N1 C9 C8 C11 0.3(3) . . . . ?
N1 C9 C8 C1 -179.4(2) . . . . ?
C17 C1 C8 C9 17.3(3) . . . . ?
C2 C1 C8 C9 -109.3(3) . . . . ?
C17 C1 C8 C11 -162.39(19) . . . . ?
C2 C1 C8 C11 71.0(3) . . . . ?
C17 C18 N2 C19 1.1(3) . . . . ?
C17 C18 N2 C25 179.3(2) . . . . ?
C18 N2 C19 C24 178.3(2) . . . . ?
C25 N2 C19 C24 0.2(4) . . . . ?
C18 N2 C19 C20 -1.2(2) . . . . ?
C25 N2 C19 C20 -179.4(2) . . . . ?
C23 C24 C19 N2 179.8(2) . . . . ?
C23 C24 C19 C20 -0.7(3) . . . . ?
C6 C7 C2 C3 1.7(3) . . . . ?
C6 C7 C2 C1 -175.1(2) . . . . ?
C8 C1 C2 C3 25.7(3) . . . . ?
C17 C1 C2 C3 -101.9(2) . . . . ?
C8 C1 C2 C7 -157.63(19) . . . . ?
C17 C1 C2 C7 74.8(2) . . . . ?
C7 C2 C3 C4 -0.9(3) . . . . ?
C1 C2 C3 C4 175.8(2) . . . . ?
C8 C9 N1 C10 0.0(3) . . . . ?
C8 C9 N1 C16 -177.2(2) . . . . ?
C22 C21 C20 C19 -0.5(3) . . . . ?
C22 C21 C20 C17 179.0(2) . . . . ?
N2 C19 C20 C21 -179.42(19) . . . . ?
C24 C19 C20 C21 1.0(3) . . . . ?
N2 C19 C20 C17 0.9(2) . . . . ?
C24 C19 C20 C17 -178.7(2) . . . . ?
C18 C17 C20 C21 -179.9(2) . . . . ?
C1 C17 C20 C21 -1.7(4) . . . . ?
C18 C17 C20 C19 -0.3(2) . . . . ?
C1 C17 C20 C19 177.8(2) . . . . ?
C9 C8 C11 C12 179.3(2) . . . . ?
C1 C8 C11 C12 -0.9(4) . . . . ?
C9 C8 C11 C10 -0.5(2) . . . . ?
C1 C8 C11 C10 179.3(2) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C8 C11 C12 C13 179.8(2) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C7 C6 C5 C4 -0.2(4) . . . . ?
C6 C5 C4 C3 1.0(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C9 N1 C10 C15 179.5(2) . . . . ?
C16 N1 C10 C15 -3.3(4) . . . . ?
C9 N1 C10 C11 -0.3(2) . . . . ?
C16 N1 C10 C11 176.9(2) . . . . ?
C12 C11 C10 N1 -179.35(19) . . . . ?
C8 C11 C10 N1 0.5(2) . . . . ?
C12 C11 C10 C15 0.9(3) . . . . ?
C8 C11 C10 C15 -179.3(2) . . . . ?
C13 C14 C15 C10 -0.1(4) . . . . ?
N1 C10 C15 C14 179.7(2) . . . . ?
C11 C10 C15 C14 -0.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.035
