# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       Karl.Tornroos@uib.no
_publ_contact_author_name        'Karl Wilhelm Tornroos'
loop_
_publ_author_name
'Karel Vervisch'
'Matthias Dhooghe'
'K. W. Tornroos '
'Norbert De Kimpe'

data_kv234
_database_code_depnum_ccdc_archive 'CCDC 849690'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N2'
_chemical_formula_sum            'C20 H22 N2'
_chemical_formula_weight         290.40

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_HALL  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7575(3)
_cell_length_b                   10.4335(5)
_cell_length_c                   14.3548(7)
_cell_angle_alpha                74.9440(10)
_cell_angle_beta                 84.1930(10)
_cell_angle_gamma                77.5330(10)
_cell_volume                     812.14(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    6774
_cell_measurement_theta_min      2.215
_cell_measurement_theta_max      28.70

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.706
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
SADABS version 2008/1, G.M Sheldrick, University of
G\"ttingen, Germany, 2008.
;

_exptl_special_details           
;
Data collection was performed on a Bruker Ultra TXS Mo rotating anode
with a PT^135^ CCD detector. Data were collected performing
four 182 degree omega scans in four orthogonal phi settings.
Cooling was achieved with a Oxford Cryosystems Series 700 blower.
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS Rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12358
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         28.77
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.77
_diffrn_measured_fraction_theta_full 0.998
_reflns_number_total             4224
_reflns_number_gt                3688
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       
;
Bruker (2008). APEX2, version 2008.5-0, Bruker AXS Inc., Madison,
Wisconsin, USA.
;
_computing_cell_refinement       
;
Bruker (2008). SAINT, version 7.56A, Bruker AXS Inc., Madison,
Wisconsin, USA.
;
_computing_data_reduction        
;
Bruker (2008). SAINT, version 7.56A, Bruker AXS Inc., Madison,
Wisconsin, USA.
;
_computing_structure_solution    
;
Sheldrick, G. M. (2008). Acta Crystallographica, A64, 112-122.
;
_computing_structure_refinement  
;
Sheldrick, G. M. (2008). Acta Crystallographica, A64, 112-122.
;
_computing_molecular_graphics    
;
Brandenburg, K. (2009). DIAMOND. Version 3.2c. Crystal Impact GbR, Bonn,
Germany.
;
_computing_publication_material  
;
Bruker AXS (2008). SHELXTL. Version 2008/1. Bruker AXS Inc., Madison,
Wisconsin, USA.
;

_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^)+(0.0642P)^2^+0.2362P] 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_number_reflns         4224
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1293
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.042

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 0.47118(16) 0.39964(9) 0.26869(6) 0.0235(2) Uani 1 1 d . . .
C1 C 0.60072(18) 0.26467(11) 0.31522(8) 0.0233(2) Uani 1 1 d . . .
H1A H 0.7525 0.2734 0.3391 0.028 Uiso 1 1 calc R . .
N2 N 0.2794(2) 0.16508(12) 0.16210(8) 0.0402(3) Uani 1 1 d . . .
C2 C 0.44899(19) 0.19894(11) 0.40146(8) 0.0249(2) Uani 1 1 d . . .
H2A H 0.3065 0.1821 0.3769 0.030 Uiso 1 1 calc R . .
H2B H 0.5424 0.1102 0.4345 0.030 Uiso 1 1 calc R . .
C3 C 0.36816(18) 0.28427(11) 0.47502(8) 0.0233(2) Uani 1 1 d . . .
H3A H 0.5138 0.2927 0.5036 0.028 Uiso 1 1 calc R . .
C4 C 0.24779(19) 0.42682(11) 0.42109(8) 0.0255(2) Uani 1 1 d . . .
H4A H 0.0966 0.4227 0.3958 0.031 Uiso 1 1 calc R . .
H4B H 0.2102 0.4866 0.4663 0.031 Uiso 1 1 calc R . .
C5 C 0.4103(2) 0.48470(11) 0.33814(8) 0.0259(2) Uani 1 1 d . . .
H5A H 0.3306 0.5768 0.3045 0.031 Uiso 1 1 calc R . .
H5B H 0.5584 0.4923 0.3641 0.031 Uiso 1 1 calc R . .
C6 C 0.65956(19) 0.17110(11) 0.24511(8) 0.0266(2) Uani 1 1 d . . .
H6A H 0.7801 0.2032 0.1953 0.032 Uiso 1 1 calc R . .
H6B H 0.7287 0.0782 0.2812 0.032 Uiso 1 1 calc R . .
C7 C 0.4465(2) 0.16822(12) 0.19776(8) 0.0294(2) Uani 1 1 d . . .
C8 C 0.60220(19) 0.47021(12) 0.18395(8) 0.0274(2) Uani 1 1 d . . .
H8A H 0.6753 0.4063 0.1440 0.033 Uiso 1 1 calc R . .
H8B H 0.7316 0.5026 0.2059 0.033 Uiso 1 1 calc R . .
C9 C 0.43674(19) 0.58937(11) 0.12370(8) 0.0256(2) Uani 1 1 d . . .
C10 C 0.2412(2) 0.56706(12) 0.08373(8) 0.0290(2) Uani 1 1 d . . .
H10A H 0.2118 0.4779 0.0959 0.035 Uiso 1 1 calc R . .
C11 C 0.0901(2) 0.67413(13) 0.02650(8) 0.0311(3) Uani 1 1 d . . .
H11A H -0.0413 0.6577 -0.0005 0.037 Uiso 1 1 calc R . .
C12 C 0.1302(2) 0.80547(13) 0.00847(8) 0.0315(3) Uani 1 1 d . . .
H12A H 0.0267 0.8785 -0.0308 0.038 Uiso 1 1 calc R . .
C13 C 0.3220(2) 0.82897(12) 0.04818(9) 0.0318(3) Uani 1 1 d . . .
H13A H 0.3498 0.9184 0.0364 0.038 Uiso 1 1 calc R . .
C14 C 0.4745(2) 0.72100(12) 0.10551(8) 0.0291(2) Uani 1 1 d . . .
H14A H 0.6058 0.7378 0.1324 0.035 Uiso 1 1 calc R . .
C15 C 0.20715(18) 0.22316(10) 0.55738(8) 0.0229(2) Uani 1 1 d . . .
C16 C 0.2208(2) 0.24103(11) 0.64978(8) 0.0269(2) Uani 1 1 d . . .
H16A H 0.3400 0.2846 0.6613 0.032 Uiso 1 1 calc R . .
C17 C 0.0630(2) 0.19617(12) 0.72505(8) 0.0287(2) Uani 1 1 d . . .
H17A H 0.0731 0.2111 0.7869 0.034 Uiso 1 1 calc R . .
C18 C -0.10924(19) 0.12976(11) 0.71013(8) 0.0269(2) Uani 1 1 d . . .
H18A H -0.2168 0.0988 0.7615 0.032 Uiso 1 1 calc R . .
C19 C -0.12276(19) 0.10899(12) 0.61938(9) 0.0281(2) Uani 1 1 d . . .
H19A H -0.2392 0.0628 0.6088 0.034 Uiso 1 1 calc R . .
C20 C 0.03320(19) 0.15539(12) 0.54368(8) 0.0270(2) Uani 1 1 d . . .
H20A H 0.0214 0.1409 0.4818 0.032 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
N1 0.0212(4) 0.0236(4) 0.0231(4) -0.0039(3) 0.0018(3) -0.0022(3)
C1 0.0182(4) 0.0253(5) 0.0252(5) -0.0062(4) -0.0011(4) -0.0014(4)
N2 0.0449(6) 0.0455(6) 0.0334(6) -0.0067(5) -0.0037(5) -0.0188(5)
C2 0.0238(5) 0.0230(5) 0.0255(5) -0.0046(4) 0.0010(4) -0.0021(4)
C3 0.0206(5) 0.0249(5) 0.0235(5) -0.0048(4) 0.0002(4) -0.0045(4)
C4 0.0252(5) 0.0236(5) 0.0259(5) -0.0059(4) 0.0019(4) -0.0028(4)
C5 0.0267(5) 0.0231(5) 0.0271(5) -0.0057(4) 0.0020(4) -0.0051(4)
C6 0.0241(5) 0.0270(5) 0.0270(5) -0.0081(4) 0.0013(4) -0.0006(4)
C7 0.0344(6) 0.0287(5) 0.0251(5) -0.0065(4) 0.0022(4) -0.0079(4)
C8 0.0218(5) 0.0308(6) 0.0258(5) -0.0029(4) 0.0028(4) -0.0036(4)
C9 0.0234(5) 0.0295(5) 0.0214(5) -0.0041(4) 0.0028(4) -0.0044(4)
C10 0.0296(5) 0.0303(6) 0.0278(5) -0.0082(4) 0.0000(4) -0.0068(4)
C11 0.0267(5) 0.0404(6) 0.0273(5) -0.0125(5) -0.0022(4) -0.0035(5)
C12 0.0306(6) 0.0347(6) 0.0234(5) -0.0048(4) 0.0012(4) 0.0021(5)
C13 0.0327(6) 0.0294(6) 0.0306(6) -0.0046(4) 0.0058(5) -0.0072(5)
C14 0.0250(5) 0.0341(6) 0.0281(5) -0.0059(4) 0.0022(4) -0.0094(4)
C15 0.0203(5) 0.0222(5) 0.0244(5) -0.0036(4) -0.0008(4) -0.0027(4)
C16 0.0267(5) 0.0283(5) 0.0286(5) -0.0095(4) 0.0002(4) -0.0090(4)
C17 0.0312(6) 0.0301(5) 0.0263(5) -0.0097(4) 0.0015(4) -0.0071(4)
C18 0.0240(5) 0.0247(5) 0.0296(5) -0.0054(4) 0.0041(4) -0.0041(4)
C19 0.0217(5) 0.0309(5) 0.0326(6) -0.0072(4) -0.0017(4) -0.0082(4)
C20 0.0240(5) 0.0333(6) 0.0244(5) -0.0059(4) -0.0030(4) -0.0073(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
N1 C1 1.4643(13) . ?
N1 C5 1.4694(14) . ?
N1 C8 1.4763(13) . ?
C1 C2 1.5378(14) . ?
C1 C6 1.5425(15) . ?
C1 H1A 1.0000 . ?
N2 C7 1.1448(16) . ?
C2 C3 1.5279(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C15 1.5184(14) . ?
C3 C4 1.5353(15) . ?
C3 H3A 1.0000 . ?
C4 C5 1.5177(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.4708(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.5159(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.3902(16) . ?
C9 C10 1.4013(16) . ?
C10 C11 1.3885(16) . ?
C10 H10A 0.9500 . ?
C11 C12 1.3921(18) . ?
C11 H11A 0.9500 . ?
C12 C13 1.3862(18) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3983(17) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 C16 1.3985(15) . ?
C15 C20 1.3999(15) . ?
C16 C17 1.3910(15) . ?
C16 H16A 0.9500 . ?
C17 C18 1.3877(16) . ?
C17 H17A 0.9500 . ?
C18 C19 1.3872(16) . ?
C18 H18A 0.9500 . ?
C19 C20 1.3923(15) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?

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
C1 N1 C5 110.53(8) . . ?
C1 N1 C8 113.60(8) . . ?
C5 N1 C8 108.97(8) . . ?
N1 C1 C2 109.69(8) . . ?
N1 C1 C6 111.85(9) . . ?
C2 C1 C6 108.22(9) . . ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
C6 C1 H1A 109.0 . . ?
C3 C2 C1 113.87(9) . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C15 C3 C2 113.96(9) . . ?
C15 C3 C4 111.35(8) . . ?
C2 C3 C4 108.33(8) . . ?
C15 C3 H3A 107.7 . . ?
C2 C3 H3A 107.7 . . ?
C4 C3 H3A 107.7 . . ?
C5 C4 C3 110.35(8) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 C4 111.76(9) . . ?
N1 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
N1 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C1 111.62(9) . . ?
C7 C6 H6A 109.3 . . ?
C1 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C1 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N2 C7 C6 179.06(13) . . ?
N1 C8 C9 110.75(8) . . ?
N1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C14 C9 C10 118.55(10) . . ?
C14 C9 C8 121.95(10) . . ?
C10 C9 C8 119.49(10) . . ?
C11 C10 C9 120.59(11) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C10 C11 C12 120.37(11) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C13 C12 C11 119.59(11) . . ?
C13 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
C12 C13 C14 119.99(11) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C9 C14 C13 120.91(11) . . ?
C9 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C16 C15 C20 117.80(10) . . ?
C16 C15 C3 119.66(9) . . ?
C20 C15 C3 122.44(9) . . ?
C17 C16 C15 121.20(10) . . ?
C17 C16 H16A 119.4 . . ?
C15 C16 H16A 119.4 . . ?
C18 C17 C16 120.26(10) . . ?
C18 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C19 C18 C17 119.35(10) . . ?
C19 C18 H18A 120.3 . . ?
C17 C18 H18A 120.3 . . ?
C18 C19 C20 120.43(10) . . ?
C18 C19 H19A 119.8 . . ?
C20 C19 H19A 119.8 . . ?
C19 C20 C15 120.95(10) . . ?
C19 C20 H20A 119.5 . . ?
C15 C20 H20A 119.5 . . ?

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 57.89(11) . . . . ?
C8 N1 C1 C2 -179.26(9) . . . . ?
C5 N1 C1 C6 177.98(8) . . . . ?
C8 N1 C1 C6 -59.17(12) . . . . ?
N1 C1 C2 C3 -55.21(11) . . . . ?
C6 C1 C2 C3 -177.48(8) . . . . ?
C1 C2 C3 C15 176.83(8) . . . . ?
C1 C2 C3 C4 52.29(11) . . . . ?
C15 C3 C4 C5 -179.03(9) . . . . ?
C2 C3 C4 C5 -52.95(11) . . . . ?
C1 N1 C5 C4 -61.91(11) . . . . ?
C8 N1 C5 C4 172.58(8) . . . . ?
C3 C4 C5 N1 59.38(12) . . . . ?
N1 C1 C6 C7 -51.97(12) . . . . ?
C2 C1 C6 C7 68.97(11) . . . . ?
C1 C6 C7 N2 -68(8) . . . . ?
C1 N1 C8 C9 164.39(9) . . . . ?
C5 N1 C8 C9 -71.91(11) . . . . ?
N1 C8 C9 C14 120.88(11) . . . . ?
N1 C8 C9 C10 -60.01(13) . . . . ?
C14 C9 C10 C11 0.58(16) . . . . ?
C8 C9 C10 C11 -178.55(10) . . . . ?
C9 C10 C11 C12 -0.36(17) . . . . ?
C10 C11 C12 C13 -0.11(17) . . . . ?
C11 C12 C13 C14 0.34(17) . . . . ?
C10 C9 C14 C13 -0.35(17) . . . . ?
C8 C9 C14 C13 178.76(10) . . . . ?
C12 C13 C14 C9 -0.10(17) . . . . ?
C2 C3 C15 C16 145.65(10) . . . . ?
C4 C3 C15 C16 -91.45(12) . . . . ?
C2 C3 C15 C20 -38.24(14) . . . . ?
C4 C3 C15 C20 84.66(12) . . . . ?
C20 C15 C16 C17 -1.64(16) . . . . ?
C3 C15 C16 C17 174.65(10) . . . . ?
C15 C16 C17 C18 1.36(17) . . . . ?
C16 C17 C18 C19 -0.20(17) . . . . ?
C17 C18 C19 C20 -0.62(17) . . . . ?
C18 C19 C20 C15 0.31(17) . . . . ?
C16 C15 C20 C19 0.80(16) . . . . ?
C3 C15 C20 C19 -175.38(10) . . . . ?