# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_sn_132_999
_database_code_depnum_ccdc_archive 'CCDC 982795'
_audit_update_record             
;
2014-01-22 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N2'
_chemical_formula_weight         250.33

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                   8.2782(2)
_cell_length_b                   7.7779(2)
_cell_length_c                   23.1597(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.957(2)
_cell_angle_gamma                90.00
_cell_volume                     1468.72(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4589
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      21.96

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_correction_T_min  0.6819
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS-2008

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19269
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         26.40
_reflns_number_total             3008
_reflns_number_gt                1970
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT  A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.1000P)²+0.0920P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.031(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3008
_refine_ls_number_parameters     177
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.2029
_refine_ls_wR_factor_gt          0.1783
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_restrained_S_all      1.355
_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 0.9890(2) 0.3640(3) 0.12945(8) 0.0775(6) Uani 1 1 d . . .
N1 N 0.9688(2) 0.3149(3) 0.02639(8) 0.0794(6) Uani 1 1 d D . .
C1 C 0.9771(2) 0.3264(3) 0.07875(9) 0.0639(6) Uani 1 1 d . . .
C2 C 1.1258(3) 0.1846(4) -0.06115(12) 0.0993(9) Uani 1 1 d . . .
H2A H 1.1541 0.3039 -0.0629 0.149 Uiso 1 1 calc R . .
H2B H 1.1589 0.1245 -0.0934 0.149 Uiso 1 1 calc R . .
H2C H 1.1808 0.1362 -0.0249 0.149 Uiso 1 1 calc R . .
C4 C 0.8383(3) 0.2198(4) 0.21907(13) 0.0934(8) Uani 1 1 d . . .
H4A H 0.8110 0.1742 0.2547 0.140 Uiso 1 1 calc R . .
H4B H 0.8034 0.1408 0.1875 0.140 Uiso 1 1 calc R . .
H4C H 0.7840 0.3281 0.2104 0.140 Uiso 1 1 calc R . .
C5 C 1.3378(3) 0.4111(4) 0.13797(12) 0.0995(8) Uani 1 1 d . . .
H5A H 1.4531 0.4287 0.1510 0.149 Uiso 1 1 calc R . .
H5B H 1.2862 0.5192 0.1264 0.149 Uiso 1 1 calc R . .
H5C H 1.3215 0.3336 0.1052 0.149 Uiso 1 1 calc R . .
C3 C 0.6182(3) 0.2834(5) 0.02718(13) 0.1084(10) Uani 1 1 d . . .
H3A H 0.5013 0.2733 0.0167 0.163 Uiso 1 1 calc R . .
H3B H 0.6473 0.4021 0.0338 0.163 Uiso 1 1 calc R . .
H3C H 0.6554 0.2188 0.0623 0.163 Uiso 1 1 calc R . .
C17 C 1.0934(2) 0.3112(2) 0.18120(8) 0.0586(5) Uani 1 1 d . . .
C12 C 1.0210(3) 0.2451(3) 0.22634(10) 0.0658(6) Uani 1 1 d . . .
C13 C 1.2631(3) 0.3354(3) 0.18729(9) 0.0672(6) Uani 1 1 d . . .
C11 C 0.6985(3) 0.2137(3) -0.02224(10) 0.0755(7) Uani 1 1 d . . .
C6 C 0.8662(2) 0.2280(3) -0.02018(8) 0.0614(5) Uani 1 1 d D . .
C7 C 0.9440(3) 0.1675(3) -0.06471(9) 0.0708(6) Uani 1 1 d . . .
C14 C 1.1210(3) 0.2006(3) 0.27809(10) 0.0810(7) Uani 1 1 d . . .
H14 H 1.0751 0.1554 0.3087 0.097 Uiso 1 1 calc R . .
C16 C 1.3571(3) 0.2890(3) 0.24019(12) 0.0829(7) Uani 1 1 d . . .
H16 H 1.4703 0.3034 0.2456 0.100 Uiso 1 1 calc R . .
C8 C 0.8471(4) 0.0888(3) -0.11261(11) 0.0907(8) Uani 1 1 d . . .
H8 H 0.8951 0.0459 -0.1431 0.109 Uiso 1 1 calc R . .
C15 C 1.2882(3) 0.2223(3) 0.28482(11) 0.0875(8) Uani 1 1 d . . .
H15 H 1.3545 0.1915 0.3199 0.105 Uiso 1 1 calc R . .
C9 C 0.6800(4) 0.0746(4) -0.11483(12) 0.0981(9) Uani 1 1 d . . .
H9 H 0.6156 0.0231 -0.1471 0.118 Uiso 1 1 calc R . .
C10 C 0.6090(3) 0.1355(4) -0.07005(12) 0.0926(8) Uani 1 1 d . . .
H10 H 0.4963 0.1234 -0.0721 0.111 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 1.197(2) . ?
N2 C17 1.412(2) . ?
N1 C1 1.206(3) . ?
N1 C6 1.422(3) . ?
C2 C7 1.499(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C4 C12 1.505(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C13 1.509(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C3 C11 1.519(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C17 C12 1.391(3) . ?
C17 C13 1.400(3) . ?
C12 C14 1.378(3) . ?
C13 C16 1.381(3) . ?
C11 C10 1.364(3) . ?
C11 C6 1.385(3) . ?
C6 C7 1.389(3) . ?
C7 C8 1.393(3) . ?
C14 C15 1.376(3) . ?
C14 H14 0.9300 . ?
C16 C15 1.366(4) . ?
C16 H16 0.9300 . ?
C8 C9 1.379(4) . ?
C8 H8 0.9300 . ?
C15 H15 0.9300 . ?
C9 C10 1.363(4) . ?
C9 H9 0.9300 . ?
C10 H10 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
C1 N2 C17 134.1(2) . . ?
C1 N1 C6 136.1(2) . . ?
N2 C1 N1 170.0(2) . . ?
C7 C2 H2A 109.5 . . ?
C7 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C7 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C12 C4 H4A 109.5 . . ?
C12 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C12 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C13 C5 H5A 109.5 . . ?
C13 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C13 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C3 H3A 109.5 . . ?
C11 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C11 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C12 C17 C13 121.98(19) . . ?
C12 C17 N2 117.75(18) . . ?
C13 C17 N2 120.15(18) . . ?
C14 C12 C17 118.3(2) . . ?
C14 C12 C4 120.4(2) . . ?
C17 C12 C4 121.3(2) . . ?
C16 C13 C17 117.1(2) . . ?
C16 C13 C5 122.1(2) . . ?
C17 C13 C5 120.8(2) . . ?
C10 C11 C6 117.7(2) . . ?
C10 C11 C3 121.6(2) . . ?
C6 C11 C3 120.8(2) . . ?
C11 C6 C7 122.5(2) . . ?
C11 C6 N1 121.8(2) . . ?
C7 C6 N1 115.54(19) . . ?
C6 C7 C8 117.6(2) . . ?
C6 C7 C2 121.3(2) . . ?
C8 C7 C2 121.1(2) . . ?
C15 C14 C12 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C12 C14 H14 119.7 . . ?
C15 C16 C13 121.7(2) . . ?
C15 C16 H16 119.2 . . ?
C13 C16 H16 119.2 . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 121.8(2) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?

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
C17 N2 C1 N1 -122.3(12) . . . . ?
C6 N1 C1 N2 -136.4(12) . . . . ?
C1 N2 C17 C12 -123.4(3) . . . . ?
C1 N2 C17 C13 60.4(3) . . . . ?
C13 C17 C12 C14 -0.9(3) . . . . ?
N2 C17 C12 C14 -176.98(19) . . . . ?
C13 C17 C12 C4 180.0(2) . . . . ?
N2 C17 C12 C4 3.9(3) . . . . ?
C12 C17 C13 C16 0.7(3) . . . . ?
N2 C17 C13 C16 176.71(19) . . . . ?
C12 C17 C13 C5 -178.6(2) . . . . ?
N2 C17 C13 C5 -2.6(3) . . . . ?
C10 C11 C6 C7 0.6(3) . . . . ?
C3 C11 C6 C7 -179.4(2) . . . . ?
C10 C11 C6 N1 176.9(2) . . . . ?
C3 C11 C6 N1 -3.1(3) . . . . ?
C1 N1 C6 C11 39.1(4) . . . . ?
C1 N1 C6 C7 -144.3(3) . . . . ?
C11 C6 C7 C8 -0.5(3) . . . . ?
N1 C6 C7 C8 -177.03(19) . . . . ?
C11 C6 C7 C2 -179.9(2) . . . . ?
N1 C6 C7 C2 3.6(3) . . . . ?
C17 C12 C14 C15 0.4(3) . . . . ?
C4 C12 C14 C15 179.5(2) . . . . ?
C17 C13 C16 C15 -0.1(3) . . . . ?
C5 C13 C16 C15 179.3(2) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C2 C7 C8 C9 179.9(2) . . . . ?
C13 C16 C15 C14 -0.4(4) . . . . ?
C12 C14 C15 C16 0.2(4) . . . . ?
C7 C8 C9 C10 -0.7(4) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C6 C11 C10 C9 -0.7(4) . . . . ?
C3 C11 C10 C9 179.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.032
